Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
Bis(
L-glutamic acid) sulfate hemihydrate
B. Sridhar,aN. Srinivasanb and
R. K. Rajarama*
aDepartment of Physics, Madurai Kamaraj
University, Madurai 625 021, India, and bDepartment of Physics, Thiagarajar College,
Madurai 625 009, India
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.006 AÊ
Rfactor = 0.033
wRfactor = 0.087 Data-to-parameter ratio = 6.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The unit cell of the crystal structure of the title compound, 2C5H10NO4SO40.5H2O, contains eight crystallographically
independent glutamic acid residues protonated at the N atom, four sulfate anions and two water molecules. The glutamic acid residues are in different conformations. Both the - and -carboxyl groups are involved in strong OÐH O hydrogen bonding; at the same time each residue shows a different hydrogen-bonding scheme. Owing to the differences in conformational features and hydrogen-bonding patterns of each residue, there is no pseudosymmetry or higher symmetry in the structure.
Comment
Glutamic acid is a dicarboxylic amino acid which is a signi®-cant constituent in proteins. It also plays an important role in the metabolism of sugar and fats. The crystal structures of
l-glutamic acid (Hirokawa, 1955), l-glutamic acid hydro-chloride (Sequeiraet al., 1972),dl-glutamic acid monohydrate (Ciunik & Glowiak, 1983) and anhydrous dl-glutamic acid (Dunitz & Schweizer, 1995) have been reported. In order to determine the hydrogen-bonding pattern and the conforma-tion of protonated glutamic acid caconforma-tion in the crystal structure of its sulfate, the X-ray diffraction study of the title compound, (I), was undertaken.
The unit cell contains eight crystallographically indepen-dent protonated glutamic acid residues, four indepenindepen-dent sulfate anions and two water molecules (Fig. 1). An attempt to look for higher symmetry using theLEPAGEprogram (Spek, 1999) resulted in aC-centred monoclinic cell with a transfor-mation (100/102/010). However, the intensity data did not conform to a monoclinic system (Rint= 0.58).
The average bond lengths and angles of the sulfate anions con®rm nearly ideal tetrahedral symmetry. The geometries of the glutamic acid residues agree well with l-glutamic acid hydrochloride (Sequeiraet al., 1972). In the present study, the doubly bonded O atoms of - and -carboxyl groups are
labelledAandC, and the single-bonded O atoms are labelled
BandD.
The backbone conformation angle 1indicates thecisform
for all eight residues. For all residues except II and III, the branched side-chain conformation angle1is in the sterically
least favoured closedgauche-I conformation, and2is in the trans form, as found in l-glutamic acid hydrochloride (Sequeiraet al., 1972). In the case of residues II and III, the conformation angle 1 is in the trans form for the former
[ÿ172.2 (6)] and the sterically most favoured opengauche-II
conformation for the latter [ÿ64.6 (4)].
The conformation angles31 and32indicate the cis and transform for all residues except for residue II, where the conformation is in the trans and cis form [ÿ179.0 (7) and
ÿ2 (1)].
All the O atoms of sulfate anions are involved in hydrogen bonding with the amino and -carboxyl groups or water molecules. This plays a vital role in stabilizing the structure (Fig. 2).
All the -carboxyl O atoms (B) form strong OÐH O hydrogen bonds with -carboxyl O atoms (C), with the exception of residues II and V, which form a strong OÐH O hydrogen bond with water molecules. These amino acids are interconnected by the hydrogen bonding as corrugated sheets, as found indl-lysine complexes (Saraswathiet al., 2001).
The -carboxyl O atoms (D) form strong OÐH O hydrogen bonds with sulfate anions in a three-dimensional hydrogen-bonding network. Interestingly, residue VIII forms a chelated OÐH O hydrogen bond with the sulfate anion.
There are three types of NÐH O hydrogen bonding in the crystal of the title compound, viz. two-centred, three-centred and chelated three-three-centred hydrogen bonding. Two-centred NÐH O hydrogen bonding is observed in the case of amino N atom with (i) the- and-carboxyl O atom (Aand
C) and (ii) the sulfate anions in all residues except residue III. It is very interesting to note that, among these, residues I and IV are involved only in two-centred NÐH O hydrogen bonds. Three-centred hydrogen bonds are observed in resi-dues II, III, V and VIII, involving the amino N and the carboxyl O atoms (A and C). Chelated three-centred hydrogen bonding is present in residues III, V, VI and VII, involving the amino N atom of the glutamic acid residue and the O atoms of the sulfate anion (Jeffrey & Saenger, 1991). Interestingly, in the case of residue III, only the three-centred and chelated type of hydrogen bonding are observed, while in the case of residue VII, two such chelated three-centred hydrogen bonds are involved.
In the amino group of residues I and IV, a class I hydrogen-bonding pattern, involving three two-centred hydrogen bonds (Jeffrey & Saenger, 1991), is present. In the case of residues II, VI and VIII, a class II hydrogen bonding, with one three-centred hydrogen bond and two two-three-centred hydrogen bonds, is observed, while in the case of residues V and VII, a class III hydrogen bond, with two three-centred hydrogen bonds and one two-centred hydrogen bond, is observed. Interestingly, in the case of residue III, the sterically least favourable class IV hydrogen-bonding pattern, with only three-centred hydrogen bonding, is observed. In general, the class II
hydrogen-Figure 1
bonding pattern is the most favoured con®guration and occurrence of class IV is rare.
Both water molecules form OÐH O hydrogen bonds with the sulfate anions and the -carboxyl group (C) of the glutamic acid residues.
In the present study, the residues are aggregated as char-acteristic layers along the diagonal plane parallel to (011). The glutamic acid residues II, IV, VI and VIII, sulfate anions 2 and 3, and the OW1 water molecule are interconnected by hydrogen-bonded ribbons as a linear chain along the diagonal (011) plane (Fig. 3). Similarly, residues I, III, Vand VII, sulfate
anions 1 and 4, and the OW2 water molecule are inter-connected by hydrogen-bonded ribbons (Fig. 4) running as an in®nite chain parallel to the same diagonal plane and lying in between two adjacent ribbons of the ®rst type.
Experimental
The title compound was crystallized by slow evaporation from an aqueous solution of l-glutamic acid and sulfuric acid in a 2:1 stoi-chiometric ratio.
Crystal data
2C5H10NO4+SO42ÿ0:5H2O
Mr= 401.35 Triclinic,P1
a= 12.536 (2) AÊ
b= 12.596 (2) AÊ
c= 13.306 (2) AÊ
= 79.09 (1)
= 62.05 (1)
= 65.88 (1) V= 1693.9 (5) AÊ3
Z= 4
Dx= 1.574 Mg mÿ3
Dm= 1.568 Mg mÿ3
Dmmeasured by ¯otation in carbon tetrachloride and xylene MoKradiation Cell parameters from 25
re¯ections
= 11.3±13.6
= 0.26 mmÿ1
T= 293 (2) K Block, colourless 0.60.60.5 mm
Figure 4
Packing diagram of the crystal, viewed down thecaxis (for the sake of clarity only glutamic acid residues I, III, Vand VII, sulfate anions 1 and 4, and the second water molecule are shown).
Figure 3
Packing diagram of the crystal, viewed down thebaxis (for the sake of clarity only glutamic acid residues II, IV, VI and VIII, sulfate anions 2 and 3, and the ®rst water molecule are shown).
Figure 2
Data collection
Enraf±Nonius CAD-4 diffractometer
!±2scans
Absorption correction: scan (Northet al., 1968)
Tmin= 0.730,Tmax= 0.776
6238 measured re¯ections 6238 independent re¯ections
5814 re¯ections withI> 2(I)
max= 25.0
h= 0!14
k=ÿ13!14
l=ÿ13!15 3 standard re¯ections
frequency: 60 min intensity decay: none
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.033
wR(F2) = 0.087
S= 1.03 6238 re¯ections 936 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.055P)2 + 0.7347P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.42 e AÊÿ3
min=ÿ0.32 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.0219 (11) Absolute structure: Flack (1983);
298 Friedel pairs Flack parameter = 0.06 (6)
Table 1
Selected geometric parameters (AÊ,).
O11AÐC111 1.213 (5) O11BÐC111 1.301 (5) C115ÐO11C 1.202 (5) C115ÐO11D 1.306 (5) O21AÐC211 1.207 (5) O21BÐC211 1.296 (5) C215ÐO21C 1.158 (6) C215ÐO21D 1.323 (6) O31AÐC311 1.195 (5) O31BÐC311 1.311 (5) C315ÐO31C 1.216 (5) C315ÐO31D 1.284 (5) O41AÐC411 1.197 (5) O41BÐC411 1.317 (5) C415ÐO41C 1.216 (5) C415ÐO41D 1.301 (5)
O51AÐC511 1.198 (4) O51BÐC511 1.297 (5) C515ÐO51C 1.227 (5) C515ÐO51D 1.290 (5) O61AÐC611 1.204 (4) O61BÐC611 1.310 (5) C615ÐO61C 1.202 (5) C615ÐO61D 1.307 (5) O71AÐC711 1.197 (5) O71BÐC711 1.313 (5) C715ÐO71C 1.197 (5) C715ÐO71D 1.304 (5) O81AÐC811 1.199 (5) O81BÐC811 1.313 (5) C815ÐO81C 1.183 (6) C815ÐO81D 1.288 (6)
O11AÐC111ÐC112ÐN111 ÿ1.9 (5) N111ÐC112ÐC113ÐC114 61.3 (5) C112ÐC113ÐC114ÐC115 175.1 (4) C113ÐC114ÐC115ÐO11C ÿ61.4 (7) C113ÐC114ÐC115ÐO11D 120.7 (5) O21AÐC211ÐC212ÐN222 ÿ29.5 (5) N222ÐC212ÐC213ÐC214 ÿ172.2 (6) C212ÐC213ÐC214ÐC215 ÿ167.5 (7) C213ÐC214ÐC215ÐO21C ÿ179.0 (7) C213ÐC214ÐC215ÐO21D ÿ1.8 (11) O31AÐC311ÐC312ÐN333 ÿ16.3 (5) N333ÐC312ÐC313ÐC314 ÿ64.6 (4) C312ÐC313ÐC314ÐC315 ÿ161.4 (3) C313ÐC314ÐC315ÐO31C 49.6 (6) C313ÐC314ÐC315ÐO31D ÿ129.7 (4) O41AÐC411ÐC412ÐN444 ÿ1.3 (5) N444ÐC412ÐC413ÐC414 67.1 (4) C412ÐC413ÐC414ÐC415 177.5 (3) C413ÐC414ÐC415ÐO41C ÿ19.5 (5) C413ÐC414ÐC415ÐO41D 161.5 (3)
O51AÐC511ÐC512ÐN555 ÿ18.2 (5) N555ÐC512ÐC513ÐC514 78.2 (4) C512ÐC513ÐC514ÐC515 170.2 (3) C513ÐC514ÐC515ÐO51C ÿ41.7 (5) C513ÐC514ÐC515ÐO51D 139.9 (3) O61AÐC611ÐC612ÐN666 ÿ6.3 (5) N666ÐC612ÐC613ÐC614 62.9 (4) C612ÐC613ÐC614ÐC615 ÿ179.7 (3) C613ÐC614ÐC615ÐO61C ÿ13.5 (5) C613ÐC614ÐC615ÐO61D 167.4 (3) O71AÐC711ÐC712ÐN777 ÿ3.1 (5) N777ÐC712ÐC713ÐC714 72.2 (4) C712ÐC713ÐC714ÐC715 168.9 (3) C713ÐC714ÐC715ÐO71C ÿ22.9 (6) C713ÐC714ÐC715ÐO71D 159.9 (4) O81AÐC811ÐC812ÐN888 ÿ7.9 (5) N888ÐC812ÐC813ÐC814 72.0 (4) C812ÐC813ÐC814ÐC815 173.0 (4) C813ÐC814ÐC815ÐO81C ÿ6.8 (9) C813ÐC814ÐC815ÐO81D 172.8 (4)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O11BÐH1B O21Ci 0.82 1.83 2.644 (4) 176
O21BÐH2B OW2ii 0.82 1.72 2.525 (5) 165
O31BÐH3B O51C 0.82 1.93 2.733 (4) 165 O41BÐH4B O71C 0.82 1.92 2.720 (4) 164 O51BÐH5B OW1 0.82 1.70 2.495 (4) 163 O61BÐH6B O41C 0.82 1.86 2.657 (4) 164 O71BÐH7B O11Ciii 0.82 1.78 2.591 (4) 169
O81BÐH8B O31Civ 0.82 1.81 2.625 (5) 177
O11DÐH1H O34v 0.82 1.77 2.585 (4) 173
O21DÐH2F O12vi 0.82 1.76 2.555 (4) 161
O31DÐH3F O14vii 0.82 1.81 2.604 (4) 162
O41DÐH4F O32 0.82 1.78 2.577 (4) 163 O51DÐH5F O41viii 0.82 1.78 2.595 (4) 172
O61DÐH6F O42iii 0.82 1.86 2.659 (4) 166
O71DÐH7F O33iii 0.82 1.86 2.625 (4) 155
O81DÐH8E O22i 0.82 2.20 2.958 (6) 153
O81DÐH8E O23i 0.82 2.39 3.081 (6) 142
N111ÐH11A O24v 0.89 1.82 2.708 (4) 171
N111ÐH11B O42viii 0.89 2.18 2.943 (5) 144
N111ÐH11C O51C 0.89 2.13 2.998 (4) 164 N222ÐH22A O24 0.89 1.89 2.767 (4) 168 N222ÐH22B O44ix 0.89 1.95 2.801 (4) 159
N222ÐH22C O51A 0.89 2.15 2.913 (4) 144 N222ÐH22C O61Cviii 0.89 2.40 2.835 (4) 110
N333ÐH33A O43 0.89 1.93 2.795 (4) 164 N333ÐH33A O44 0.89 2.46 2.992 (4) 119 N333ÐH33B O33 0.89 2.08 2.886 (4) 151 N333ÐH33B O32 0.89 2.49 3.061 (4) 122 N333ÐH33C O71Cv 0.89 2.34 3.070 (4) 139
N333ÐH33C O41Av 0.89 2.36 3.036 (4) 133
N444ÐH44A O14vii 0.89 1.92 2.804 (4) 172
N444ÐH44B O23 0.89 1.94 2.797 (5) 161 N444ÐH44C O21Ax 0.89 2.23 2.922 (4) 134
N555ÐH55A O31vii 0.89 2.15 2.928 (4) 146
N555ÐH55A O34vii 0.89 2.39 3.193 (4) 151
N555ÐH55B O11ii 0.89 1.95 2.727 (5) 145
N555ÐH55C O71Avii 0.89 2.41 3.095 (4) 134
N555ÐH55C O11Cxi 0.89 2.48 3.056 (4) 123
N666ÐH66A O34x 0.89 1.92 2.798 (4) 166
N666ÐH66A O33x 0.89 2.59 3.254 (4) 132
N666ÐH66B O13 0.89 2.02 2.844 (5) 154 N666ÐH66C O21Cxii 0.89 2.03 2.807 (4) 145
N777ÐH77A O13 0.89 2.20 2.962 (5) 143 N777ÐH77A O14 0.89 2.21 2.992 (5) 147 N777ÐH77B O22iv 0.89 1.97 2.830 (5) 162
N777ÐH77B O21iv 0.89 2.62 3.084 (5) 114
N777ÐH77C O31Civ 0.89 2.43 3.160 (5) 140
N888ÐH88A O43 0.89 1.84 2.717 (4) 169 N888ÐH88B O31 0.89 1.95 2.827 (4) 170 N888ÐH88C O41C 0.89 2.40 3.084 (4) 134 N888ÐH88C O61A 0.89 2.48 3.151 (4) 133 OW1ÐH1WA O21 0.85 (6) 1.88 (6) 2.732 (4) 175 (5) OW1ÐH1WB O61Cviii 0.79 (6) 2.07 (6) 2.803 (5) 155 (5)
OW2ÐH2WA O11 0.81 (7) 1.96 (7) 2.706 (5) 151 (6) OW2ÐH2WB O81Ciii 0.94 (8) 1.78 (8) 2.725 (6) 174 (6)
Symmetry codes: (i)x;1y;zÿ1; (ii)xÿ1;yÿ1;z; (iii)x;y;1z; (iv)x;1y;z; (v)
x;y;zÿ1; (vi)xÿ1;yÿ1;1z; (vii)x;yÿ1;z; (viii)xÿ1;y;z; (ix)xÿ1;y;1z; (x) 1x;y;z; (xi)x;yÿ1;1z; (xii) 1x;1y;zÿ1.
The H atoms attached to water molecules were located and re®ned in the isotropic approximation (OÐH = 0.79±0.94 AÊ). All other H atoms were placed in geometrically calculated positions and included in the re®nement in a riding-model approximation withUisoequal to
1.2Ueqof the carrier atom.
program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:PLATON(Spek, 1999); software used to prepare material for publication:SHELXL97.
BS and RKR thank the Department of Science and Tech-nology (DST), India, for ®nancial support.
References
Ciunik, Z. & Glowiak, T. (1983).Acta Cryst.C39, 1271±1273. Dunitz, J. D. & Schweizer, W. B. (1995).Acta Cryst.C51, 1377±1379. Enraf±Nonius (1989).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The
Netherlands.
Flack, H. D. (1983).Acta Cryst.A39, 876±881. Hirokawa, S. (1955).Acta Cryst.8, 637±641.
Jeffrey, G. A. & Saenger, W. (1991). Hydrogen Bonding in Biological Structures. Berlin, Heidelberg, New York: Springer-Verlag.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.
Saraswathi, N. T., Manoj, N. & Vijayan, M. (2001).Acta Cryst.B57, 366±371. Sequeira, A., Rajagopal, H. & Chidambaram, R. (1972). Acta Cryst.B28,
2514±2519.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of GoÈttingen, Germany.
supporting information
Acta Cryst. (2002). E58, o272–o276 [doi:10.1107/S1600536802002234]
Bis(
L-glutamic acid) sulfate hemihydrate
B. Sridhar, N. Srinivasan and R. K. Rajaram
S1. Comment
Glutamic acid is a dicarboxylic amino acid which is a significant constituent in protein. It also plays an important role in
metabolism process of sugar and fats. The crystal structures of L-glutamic acid (Hirokawa, 1955), L-glutamic acid
hydro-chloride (Sequeira et al., 1972), DL-glutamic acid monohydrate (Ciunik & Glowiak, 1983) and anhydrous DL-glutamic
acid (Dunitz & Schweizer, 1995) have been reported. In order to determine the hydrogen-bonding pattern and
conformation of protonated glutamic acid cation in the crystal of its sulfate, the X-ray diffraction study of the title
compound, (I), was undertaken.
The unit cell contains eight crystallographically independent protonated glutamic acid residues, four independent sulfate
anions and two water molecules (Fig. 1). An attempt to look for higher symmetry using the LEPAGE program (Spek,
1999) resulted in a C-centred monoclinic cell with a transformation (100/102/010). However, the intensity data did not
conform to a monoclinic system (Rint = 0.58).
The average bond lengths and angles of sulfate anions confirm its nearly ideal tetrahedral symmetry. The geometries of
the glutamic acid residues agree well with L-glutamic acid hydrochloride (Sequeira et al., 1972). In the present study, the
doubly bonded O atoms of α- and γ-carboxyl groups are labelled as A and C and the single bonded O atoms are labelled
as B and D, respectively.
The backbone conformation angle ψ1 indicates the cis form for all eight residues. The branched side-chain conformation
angle χ1 is in the sterically least-favoured closed gauche I conformation and χ2 is in the trans form for all the residues as
found in DL-glutamic acid hydrochloride (Sequeria et al., 1972) except for residues II and III. In the case of residues II
and III, the conformation angle χ1 is in trans form for the former [-172.2 (6)°] and sterically most favoured open gauche
II conformation for the latter [-64.6 (4)°].
The conformation angles χ31 and χ32 indicate the cis and trans form for all residues except for residue II where the
conformation is in trans and cis form [-179.0 (7) and -2(1)°].
All the O atoms of sulfate anions are involved in hydrogen bonding with amino and γ-carboxyl group or water
molecules. It plays a vital role in stabilizing the structure (Fig. 2).
All the α-carboxyl O atoms (B) form strong O—H···O hydrogen bonds with γ-carboxyl O atoms (C) with the exception
of residues II and V, which form a strong O—H···O hydrogen bond with water molecules. These amino acids are
interconnected by the hydrogen bonding as corrugated sheets as found in DL-lysine complexes (Saraswathi et al., 2001).
The γ-carboxyl O atoms (D) form strong O—H···O hydrogen bonds with sulfate anions in a three-dimensional
hydrogen-bonding network. Interestingly, in the case of residue VIII, it forms a chelated O—H···O hydrogen bond with
the sulfate anion.
There are three types of N—H···O hydrogen bonding in the crystal of the title compoud, viz. two-centered,
three-centered and chelated three-three-centered hydrogen bonding. Two-three-centered N–H···O hydrogen bonding is observed in the case
It is very interesting to note that among these, residue I and IV are involved only in two-centered N—H···O hydrogen
bonds. Three-centered hydrogen bonds are observed in residues II, III, V and VIII involving the amino N and the
carboxyl O atoms (A and C). Chelated three-centered hydrogen bondings are engaged in residues III, V, VI and VII
involving the amino N atom of the glutamic acid residue and the O atoms of the sulfate anion (Jeffrey & Saenger, 1991).
Interestingly, in the case of residue III, only the three-centered and chelated type of hydrogen bonding are observed, while
in the case of residue VII, two such chelated three-centered hydrogen bonds are engaged.
In the amino group of residues I and IV, a class-I hydrogen-bonding pattern, involving three two-centred hydrogen
bonding (Jeffrey & Saenger, 1991), is present. In the case of residues II, VI and VIII, a class-II hydrogen-bonding pattern,
with one three-centred hydrogen bonding and two two-centred hydrogen bonding, is observed, while in the case of
residues V and VII, a class-III hydrogen-bonding structure, with two three-centred hydrogen bonding and one
two-centred hydrogen bonding, is observed. Interestingly, in the case of residue III, the sterically least favourable class-IV
bonding pattern, with only three-centred hydrogen bonding, is observed. In general, the class-II
hydrogen-bonding pattern is the most favoured configuration and occurrence of class-IV is rare.
Both water molecules form a O—H···O hydrogen bonding with the sulfate anions and the γ-carboxyl group (C) of the
glutamic acid residues.
In the present study, the residues are aggregated as characteristic layers along the diagonal plane. The glutamic acid
residues II, IV, VI and VIII, sulfate anions 2 and 3, and the OW1 water molecule are interconnected by hydrogen-bonded
ribbons as a linear chain along the diagonal (011) plane (Fig. 3). Similarly, the residues I, III, V and VII, sulfate anions 1
and 4, and the OW2 water molecule are interconnected by hydrogen-bonded (Fig. 4) ribbons running as an infinite chain
parallel to the same diagonal plane and lying in between two adjacent ribbons of the first type.
S2. Experimental
The title compound was crystallized by slow evaporation from an aqueous solution of L-glutamic acid and sulfuric acid
in a 2:1 stoichiometric ratio.
S3. Refinement
The H atoms attached to water molecules were located and refined in the isotropic approximation (O—H = 0.79–0.94 Å).
All other H atoms were placed in geometrically calculated positions and included in the refinement in a riding-model
Figure 1
The asymmetric unit of the title compound with the atom-numbering scheme and 50% probability displacement ellipsoids
Figure 2
Figure 3
Packing diagram of the crystal viewed down the b axis (for the sake of clarity only glutamic acid residues II, IV, VI and
Figure 4
Packing diagram of the crystal viewed down the c axis (for the sake of clarity only glutamic acid residues I, III, V and
VII, sulfate anions 1 and 4, and the second water molecule are shown).
Bis(L-glutamic acid) sulfate hemihydrate
Crystal data
2C5H10NO4+·SO42−·0.5H2O
Mr = 401.35
Triclinic, P1
a = 12.536 (2) Å
b = 12.596 (2) Å
c = 13.306 (2) Å
α = 79.09 (1)°
β = 62.05 (1)°
γ = 65.88 (1)°
V = 1693.9 (5) Å3
Z = 4
F(000) = 844
Dx = 1.574 Mg m−3
Dm = 1.568 Mg m−3
Dm measured by flotation in carbon tetrachloride and xylene
µ = 0.26 mm−1
T = 293 K
0.6 × 0.6 × 0.5 mm
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω–2θ scans
Absorption correction: ψ scan (North et al., 1968)
Tmin = 0.730, Tmax = 0.776 6238 measured reflections
6238 independent reflections 5814 reflections with I > 2σ(I)
Rint = 0.000
θmax = 25.0°, θmin = 1.7°
h = 0→14
k = −13→14
l = −13→15
3 standard reflections every 60 min intensity decay: none
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.033
wR(F2) = 0.087
S = 1.03 6238 reflections 936 parameters 3 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.055P)2 + 0.7347P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.42 e Å−3 Δρmin = −0.32 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0219 (11)
Absolute structure: Flack, (1983); 298 Friedel pairs
Absolute structure parameter: 0.06 (6)
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
S1 0.89414 (8) 0.83198 (7) 0.55962 (7) 0.0280 (2)
O11 0.9579 (3) 0.8278 (5) 0.6275 (3) 0.0851 (15)
O12 0.9784 (3) 0.8449 (3) 0.4415 (2) 0.0557 (8)
O13 0.8625 (4) 0.7303 (3) 0.5734 (4) 0.0833 (14)
O14 0.7679 (3) 0.9309 (3) 0.6012 (2) 0.0473 (7)
S2 0.39345 (9) 0.07025 (7) 0.82172 (8) 0.0292 (2)
O21 0.4676 (3) 0.0820 (3) 0.7006 (2) 0.0468 (7)
O22 0.4032 (4) −0.0497 (3) 0.8480 (4) 0.0870 (16)
O24 0.2566 (3) 0.1465 (2) 0.8577 (2) 0.0384 (6) S3 0.35802 (8) 0.55049 (7) 0.35519 (7) 0.02470 (19)
O31 0.4005 (3) 0.6452 (3) 0.3437 (3) 0.0454 (7)
O32 0.4490 (3) 0.4403 (2) 0.3754 (2) 0.0395 (6)
O33 0.3487 (3) 0.5374 (2) 0.2528 (2) 0.0406 (7)
O34 0.2267 (3) 0.5790 (3) 0.4510 (2) 0.0427 (7)
S4 0.86182 (8) 0.30737 (8) 0.07589 (7) 0.0279 (2)
O41 0.9563 (3) 0.2206 (3) 0.1131 (3) 0.0555 (8)
O42 0.9182 (3) 0.3919 (3) 0.0036 (3) 0.0478 (7)
O43 0.7382 (3) 0.3642 (3) 0.1714 (3) 0.0497 (8)
O44 0.8350 (3) 0.2476 (3) 0.0105 (3) 0.0529 (8)
O11A 0.0725 (3) 0.4852 (3) 0.1525 (3) 0.0494 (7) O11B 0.2397 (3) 0.5417 (3) 0.0450 (3) 0.0558 (9)
H1B 0.2002 0.5925 0.0937 0.084*
C111 0.1746 (4) 0.4748 (3) 0.0693 (3) 0.0345 (8) C112 0.2422 (4) 0.3794 (3) −0.0173 (3) 0.0316 (8)
H112 0.3250 0.3317 −0.0143 0.038*
N111 0.1664 (3) 0.3038 (3) 0.0194 (3) 0.0327 (7)
H11A 0.1938 0.2584 −0.0383 0.049*
H11B 0.0826 0.3476 0.0414 0.049*
H11C 0.1771 0.2598 0.0772 0.049*
C113 0.2755 (4) 0.4177 (4) −0.1405 (3) 0.0381 (9)
H11D 0.3288 0.4638 −0.1616 0.046*
H11E 0.3267 0.3492 −0.1888 0.046*
C114 0.1597 (5) 0.4871 (5) −0.1625 (4) 0.0590 (13)
H11F 0.1044 0.5526 −0.1103 0.071*
H11G 0.1102 0.4391 −0.1487 0.071*
C115 0.1988 (4) 0.5317 (4) −0.2841 (4) 0.0398 (9) O11C 0.2575 (3) 0.5963 (3) −0.3217 (3) 0.0448 (7) O11D 0.1605 (3) 0.4979 (3) −0.3441 (3) 0.0544 (8)
H1H 0.1854 0.5251 −0.4084 0.082*
O21A −0.1021 (3) −0.0092 (3) 0.8785 (3) 0.0467 (7) O21B 0.0550 (4) −0.1851 (3) 0.8477 (3) 0.0607 (9)
H2B 0.0047 −0.2041 0.8388 0.091*
C211 0.0047 (4) −0.0744 (3) 0.8680 (3) 0.0325 (8) C212 0.0941 (4) −0.0340 (3) 0.8853 (3) 0.0302 (8)
H21A 0.1850 −0.0800 0.8372 0.036*
N222 0.0663 (3) 0.0902 (3) 0.8553 (3) 0.0301 (7)
H22A 0.1185 0.1141 0.8653 0.045*
H22B −0.0160 0.1317 0.8997 0.045*
H22C 0.0799 0.0999 0.7829 0.045*
C213 0.0695 (5) −0.0457 (4) 1.0112 (3) 0.0453 (10)
H21B 0.1163 −0.0076 1.0227 0.054*
H21C −0.0224 −0.0071 1.0590 0.054*
C214 0.1115 (10) −0.1680 (5) 1.0450 (5) 0.118 (4)
H21D 0.2057 −0.2008 1.0072 0.142*
H21E 0.0806 −0.2086 1.0158 0.142*
O21D −0.0002 (5) −0.1038 (3) 1.2394 (3) 0.0836 (15)
H2F −0.0188 −0.1259 1.3055 0.125*
O31A 0.3345 (3) 0.2939 (3) 0.1785 (3) 0.0475 (7) O31B 0.4258 (3) 0.1011 (3) 0.1653 (3) 0.0548 (9)
H3B 0.3589 0.1073 0.1637 0.082*
C311 0.4226 (4) 0.2048 (3) 0.1729 (3) 0.0315 (8) C312 0.5440 (3) 0.1986 (3) 0.1766 (3) 0.0259 (7)
H31A 0.6203 0.1458 0.1166 0.031*
N333 0.5484 (3) 0.3168 (3) 0.1538 (3) 0.0285 (6)
H33A 0.6131 0.3177 0.1644 0.043*
H33B 0.4735 0.3674 0.2011 0.043*
H33C 0.5612 0.3365 0.0824 0.043*
C313 0.5421 (4) 0.1518 (4) 0.2918 (3) 0.0340 (8)
H31B 0.4682 0.2058 0.3507 0.041*
H31C 0.5296 0.0783 0.3056 0.041*
C314 0.6635 (5) 0.1333 (4) 0.3017 (4) 0.0431 (10)
H31D 0.7388 0.1006 0.2311 0.052*
H31E 0.6617 0.2077 0.3138 0.052*
C315 0.6756 (4) 0.0529 (3) 0.3985 (3) 0.0355 (9) O31C 0.6642 (4) −0.0410 (3) 0.4133 (3) 0.0578 (9) O31D 0.6979 (3) 0.0923 (2) 0.4660 (2) 0.0477 (8)
H3F 0.7032 0.0449 0.5166 0.072*
O41A 0.6074 (3) 0.2339 (3) 0.9270 (2) 0.0437 (7) O41B 0.7360 (4) 0.3273 (3) 0.8054 (2) 0.0531 (8)
H4B 0.6961 0.3743 0.8577 0.080*
C411 0.6931 (4) 0.2412 (3) 0.8368 (3) 0.0318 (8) C412 0.7642 (3) 0.1516 (3) 0.7427 (3) 0.0282 (8)
H41A 0.8559 0.1175 0.7278 0.034*
N444 0.7108 (3) 0.0570 (3) 0.7842 (3) 0.0306 (7)
H44A 0.7364 0.0137 0.7255 0.046*
H44B 0.6244 0.0882 0.8183 0.046*
H44C 0.7398 0.0126 0.8334 0.046*
C413 0.7568 (3) 0.2072 (3) 0.6321 (3) 0.0285 (7)
H41B 0.8042 0.2593 0.6035 0.034*
H41C 0.7987 0.1467 0.5757 0.034*
C414 0.6186 (4) 0.2747 (3) 0.6473 (3) 0.0309 (8)
H41D 0.5728 0.2214 0.6732 0.037*
H41E 0.5760 0.3323 0.7066 0.037*
C415 0.6060 (4) 0.3351 (3) 0.5430 (3) 0.0282 (7) O41C 0.6914 (3) 0.3585 (2) 0.4601 (2) 0.0370 (6) O41D 0.4898 (3) 0.3614 (2) 0.5526 (2) 0.0404 (7)
H4F 0.4850 0.3944 0.4947 0.061*
O51A 0.1523 (3) 0.0100 (2) 0.6287 (2) 0.0385 (6) O51B 0.3267 (3) 0.0384 (3) 0.4872 (3) 0.0544 (9)
H5B 0.3082 0.0900 0.5286 0.082*
H51A 0.3713 −0.1530 0.4316 0.032* N555 0.2099 (3) −0.1885 (3) 0.5303 (3) 0.0312 (7)
H55A 0.2441 −0.2535 0.4911 0.047*
H55B 0.1259 −0.1544 0.5467 0.047*
H55C 0.2191 −0.2057 0.5945 0.047*
C513 0.2459 (4) −0.0574 (3) 0.3598 (3) 0.0300 (8)
H51B 0.3133 −0.0296 0.3045 0.036*
H51C 0.2484 −0.1193 0.3240 0.036*
C514 0.1159 (4) 0.0410 (3) 0.3886 (3) 0.0332 (8)
H51D 0.0476 0.0103 0.4330 0.040*
H51E 0.1069 0.0972 0.4356 0.040*
C515 0.0975 (4) 0.1022 (3) 0.2860 (3) 0.0306 (8) O51C 0.1830 (3) 0.1266 (3) 0.2023 (2) 0.0425 (7) O51D −0.0180 (3) 0.1290 (3) 0.2961 (2) 0.0403 (7)
H5F −0.0229 0.1620 0.2382 0.060*
O61A 0.8369 (3) 0.5348 (2) 0.4112 (2) 0.0395 (6) O61B 0.9292 (3) 0.3415 (2) 0.4107 (3) 0.0435 (7)
H6B 0.8617 0.3449 0.4124 0.065*
C611 0.9269 (4) 0.4469 (3) 0.4078 (3) 0.0285 (8) C612 1.0502 (3) 0.4451 (3) 0.4043 (3) 0.0285 (7)
H61A 1.1244 0.4009 0.3371 0.034*
N666 1.0443 (3) 0.5678 (3) 0.3925 (3) 0.0365 (8)
H66A 1.1110 0.5694 0.3992 0.055*
H66B 0.9702 0.6117 0.4467 0.055*
H66C 1.0482 0.5952 0.3246 0.055*
C613 1.0684 (3) 0.3875 (3) 0.5101 (3) 0.0271 (7)
H61B 1.0783 0.3067 0.5122 0.032*
H61C 1.1477 0.3889 0.5047 0.032*
C614 0.9554 (4) 0.4468 (3) 0.6203 (3) 0.0308 (8)
H61D 0.9453 0.5277 0.6175 0.037*
H61E 0.8764 0.4450 0.6253 0.037*
C615 0.9708 (4) 0.3927 (3) 0.7254 (3) 0.0302 (8) O61C 1.0507 (3) 0.2991 (2) 0.7278 (3) 0.0468 (8) O61D 0.8856 (3) 0.4590 (2) 0.8149 (2) 0.0387 (6)
H6F 0.8967 0.4272 0.8708 0.058*
O71A 0.3825 (3) 0.7818 (2) 0.6482 (2) 0.0401 (6) O71B 0.4783 (3) 0.5892 (3) 0.6526 (3) 0.0572 (9)
H7B 0.4131 0.5898 0.6518 0.086*
C711 0.4713 (4) 0.6965 (3) 0.6501 (3) 0.0312 (8) C712 0.5906 (3) 0.6984 (3) 0.6516 (3) 0.0270 (7)
H71A 0.6666 0.6576 0.5834 0.032*
N777 0.5790 (3) 0.8212 (3) 0.6438 (3) 0.0376 (8)
H77A 0.6510 0.8240 0.6392 0.056*
H77B 0.5111 0.8598 0.7055 0.056*
H77C 0.5680 0.8536 0.5822 0.056*
C713 0.6097 (4) 0.6352 (3) 0.7557 (3) 0.0324 (8)
H71B 0.6373 0.5523 0.7462 0.039*
H71D 0.4715 0.7523 0.8833 0.051*
H71E 0.4162 0.6748 0.8578 0.051*
C715 0.4956 (4) 0.5986 (3) 0.9683 (3) 0.0329 (8) O71C 0.5668 (3) 0.4991 (2) 0.9635 (2) 0.0443 (7) O71D 0.4088 (3) 0.6557 (2) 1.0626 (2) 0.0459 (7)
H7F 0.4135 0.6140 1.1170 0.069*
O81A 0.6027 (3) 0.7434 (2) 0.3993 (2) 0.0404 (6) O81B 0.7564 (4) 0.8013 (3) 0.2601 (3) 0.0618 (10)
H8B 0.7294 0.8519 0.3060 0.093*
C811 0.6904 (4) 0.7324 (3) 0.3057 (3) 0.0333 (8) C812 0.7377 (4) 0.6371 (3) 0.2228 (3) 0.0292 (7)
H812 0.8308 0.5942 0.2002 0.035*
N888 0.6689 (3) 0.5565 (3) 0.2860 (3) 0.0304 (7)
H88A 0.7017 0.4946 0.2430 0.046*
H88B 0.5847 0.5926 0.3035 0.046*
H88C 0.6789 0.5339 0.3496 0.046*
C813 0.7192 (4) 0.6863 (3) 0.1156 (3) 0.0333 (8)
H81A 0.7374 0.6224 0.0719 0.040*
H81B 0.7823 0.7223 0.0695 0.040*
C814 0.5837 (4) 0.7757 (3) 0.1374 (3) 0.0370 (9)
H81C 0.5218 0.7371 0.1753 0.044*
H81D 0.5612 0.8346 0.1889 0.044*
C815 0.5697 (5) 0.8343 (5) 0.0336 (4) 0.0550 (13) O81C 0.6571 (4) 0.8227 (7) −0.0583 (4) 0.163 (4) O81D 0.4519 (3) 0.8995 (3) 0.0523 (3) 0.0501 (8)
H8E 0.4502 0.9294 −0.0076 0.075*
OW1 0.3168 (4) 0.1925 (3) 0.5882 (3) 0.0419 (7)
H1WA 0.360 (5) 0.158 (4) 0.627 (4) 0.053 (15)*
H1WB 0.250 (6) 0.237 (5) 0.630 (4) 0.049 (16)*
OW2 0.9207 (4) 0.7206 (3) 0.8310 (3) 0.0481 (8)
H2WA 0.923 (6) 0.736 (6) 0.768 (6) 0.08 (2)*
H2WB 0.830 (8) 0.761 (6) 0.868 (6) 0.09 (2)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O51A 0.0432 (16) 0.0427 (15) 0.0257 (14) −0.0182 (13) −0.0085 (13) −0.0037 (11) O51B 0.062 (2) 0.068 (2) 0.0406 (17) −0.0471 (18) −0.0078 (15) −0.0036 (15) C511 0.035 (2) 0.0334 (19) 0.0254 (18) −0.0141 (16) −0.0163 (17) 0.0038 (14) C512 0.0214 (16) 0.0280 (17) 0.0250 (17) −0.0076 (14) −0.0079 (14) −0.0001 (13) N555 0.0363 (17) 0.0231 (15) 0.0297 (16) −0.0089 (13) −0.0139 (14) 0.0031 (12) C513 0.035 (2) 0.0279 (17) 0.0228 (17) −0.0077 (15) −0.0114 (15) −0.0020 (13) C514 0.0310 (19) 0.0350 (19) 0.0278 (18) −0.0118 (16) −0.0105 (16) 0.0052 (15) C515 0.034 (2) 0.0284 (18) 0.036 (2) −0.0153 (15) −0.0187 (17) 0.0046 (15) O51C 0.0392 (16) 0.0562 (18) 0.0399 (16) −0.0278 (14) −0.0227 (14) 0.0225 (13) O51D 0.0359 (15) 0.0493 (17) 0.0443 (16) −0.0212 (13) −0.0236 (13) 0.0109 (13) O61A 0.0320 (14) 0.0397 (15) 0.0474 (16) −0.0090 (13) −0.0222 (13) 0.0025 (12) O61B 0.0413 (17) 0.0384 (16) 0.0598 (19) −0.0158 (13) −0.0276 (15) −0.0015 (13) C611 0.0307 (19) 0.0356 (19) 0.0177 (15) −0.0112 (17) −0.0107 (14) 0.0011 (13) C612 0.0241 (18) 0.0311 (18) 0.0261 (17) −0.0080 (15) −0.0104 (15) 0.0025 (14) N666 0.0296 (17) 0.0415 (19) 0.0396 (18) −0.0201 (15) −0.0165 (15) 0.0175 (15) C613 0.0252 (17) 0.0253 (17) 0.0270 (17) −0.0038 (14) −0.0140 (15) 0.0023 (13) C614 0.0294 (19) 0.0298 (17) 0.0298 (18) −0.0081 (15) −0.0136 (16) 0.0021 (14) C615 0.0303 (19) 0.0290 (18) 0.0315 (18) −0.0150 (16) −0.0128 (16) 0.0070 (14) O61C 0.0449 (17) 0.0364 (16) 0.0388 (16) −0.0050 (14) −0.0164 (14) 0.0147 (12) O61D 0.0437 (16) 0.0430 (15) 0.0268 (13) −0.0129 (13) −0.0180 (12) 0.0057 (11) O71A 0.0324 (14) 0.0413 (15) 0.0475 (16) −0.0118 (13) −0.0223 (13) 0.0071 (12) O71B 0.059 (2) 0.0361 (16) 0.102 (3) −0.0207 (15) −0.054 (2) 0.0036 (17) C711 0.033 (2) 0.034 (2) 0.0304 (19) −0.0128 (17) −0.0173 (16) 0.0024 (15) C712 0.0232 (17) 0.0284 (18) 0.0264 (17) −0.0088 (14) −0.0100 (14) 0.0024 (14) N777 0.0368 (18) 0.0367 (18) 0.045 (2) −0.0216 (15) −0.0191 (16) 0.0092 (14) C713 0.0268 (19) 0.036 (2) 0.0290 (19) −0.0112 (16) −0.0110 (16) 0.0061 (15) C714 0.047 (2) 0.037 (2) 0.029 (2) −0.0063 (18) −0.0131 (18) 0.0038 (16) C715 0.043 (2) 0.030 (2) 0.0287 (19) −0.0155 (17) −0.0174 (17) 0.0034 (15) O71C 0.0547 (18) 0.0313 (15) 0.0336 (15) −0.0073 (14) −0.0169 (14) 0.0018 (11) O71D 0.064 (2) 0.0346 (14) 0.0272 (14) −0.0131 (14) −0.0155 (14) 0.0023 (11) O81A 0.0417 (16) 0.0386 (14) 0.0350 (15) −0.0119 (13) −0.0125 (14) −0.0055 (11) O81B 0.087 (3) 0.066 (2) 0.0490 (19) −0.056 (2) −0.0179 (18) −0.0039 (16) C811 0.038 (2) 0.0345 (19) 0.036 (2) −0.0157 (17) −0.0231 (18) 0.0053 (15) C812 0.0293 (19) 0.0290 (18) 0.0292 (18) −0.0100 (15) −0.0142 (15) 0.0027 (14) N888 0.0336 (17) 0.0269 (15) 0.0292 (15) −0.0095 (13) −0.0138 (14) −0.0004 (12) C813 0.033 (2) 0.0348 (19) 0.0262 (18) −0.0077 (16) −0.0116 (16) −0.0021 (14) C814 0.036 (2) 0.039 (2) 0.033 (2) −0.0116 (17) −0.0173 (18) 0.0063 (16) C815 0.041 (3) 0.071 (3) 0.031 (2) −0.006 (2) −0.013 (2) 0.008 (2) O81C 0.049 (3) 0.262 (8) 0.042 (2) 0.029 (4) −0.006 (2) 0.050 (3) O81D 0.0449 (18) 0.0574 (19) 0.0390 (16) −0.0075 (15) −0.0243 (14) 0.0092 (14) OW1 0.0484 (19) 0.0441 (17) 0.0383 (16) −0.0157 (15) −0.0234 (16) −0.0020 (14) OW2 0.053 (2) 0.0576 (19) 0.0414 (18) −0.0277 (17) −0.0232 (16) 0.0089 (15)
Geometric parameters (Å, º)
S1—O11 1.443 (4) C414—C415 1.496 (5)
S1—O12 1.449 (3) C414—H41E 0.9700
S1—O14 1.480 (3) C415—O41C 1.216 (5)
S2—O21 1.449 (3) C415—O41D 1.301 (5)
S2—O22 1.453 (3) O41D—H4F 0.8200
S2—O23 1.464 (4) O51A—C511 1.198 (4)
S2—O24 1.468 (3) O51B—C511 1.297 (5)
S3—O31 1.451 (3) O51B—H5B 0.8200
S3—O33 1.466 (3) C511—C512 1.512 (5)
S3—O32 1.467 (3) C512—N555 1.480 (5)
S3—O34 1.479 (3) C512—C513 1.539 (5)
S4—O43 1.456 (3) C512—H51A 0.9800
S4—O41 1.459 (3) N555—H55A 0.8900
S4—O42 1.465 (3) N555—H55B 0.8900
S4—O44 1.472 (3) N555—H55C 0.8900
O11A—C111 1.213 (5) C513—C514 1.511 (5)
O11B—C111 1.301 (5) C513—H51B 0.9700
O11B—H1B 0.8200 C513—H51C 0.9700
C111—C112 1.505 (5) C514—C515 1.504 (5)
C112—N111 1.476 (5) C514—H51D 0.9700
C112—C113 1.522 (5) C514—H51E 0.9700
C112—H112 0.9800 C515—O51C 1.227 (5)
N111—H11A 0.8900 C515—O51D 1.290 (5)
N111—H11B 0.8900 O51D—H5F 0.8200
N111—H11C 0.8900 O61A—C611 1.204 (4)
C113—C114 1.491 (6) O61B—C611 1.310 (5)
C113—H11D 0.9700 O61B—H6B 0.8200
C113—H11E 0.9700 C611—C612 1.515 (5)
C114—C115 1.520 (6) C612—N666 1.498 (5)
C114—H11F 0.9700 C612—C613 1.530 (5)
C114—H11G 0.9700 C612—H61A 0.9800
C115—O11C 1.202 (5) N666—H66A 0.8900
C115—O11D 1.306 (5) N666—H66B 0.8900
O11D—H1H 0.8200 N666—H66C 0.8900
O21A—C211 1.207 (5) C613—C614 1.522 (5)
O21B—C211 1.296 (5) C613—H61B 0.9700
O21B—H2B 0.8200 C613—H61C 0.9700
C211—C212 1.522 (5) C614—C615 1.498 (5)
C212—N222 1.476 (5) C614—H61D 0.9700
C212—C213 1.544 (5) C614—H61E 0.9700
C212—H21A 0.9800 C615—O61C 1.202 (5)
N222—H22A 0.8900 C615—O61D 1.307 (5)
N222—H22B 0.8900 O61D—H6F 0.8200
N222—H22C 0.8900 O71A—C711 1.197 (5)
C213—C214 1.466 (7) O71B—C711 1.313 (5)
C213—H21B 0.9700 O71B—H7B 0.8200
C213—H21C 0.9700 C711—C712 1.515 (5)
C214—C215 1.513 (7) C712—N777 1.482 (5)
C215—O21C 1.158 (6) N777—H77A 0.8900
C215—O21D 1.323 (6) N777—H77B 0.8900
O21D—H2F 0.8200 N777—H77C 0.8900
O31A—C311 1.195 (5) C713—C714 1.513 (5)
O31B—C311 1.311 (5) C713—H71B 0.9700
O31B—H3B 0.8200 C713—H71C 0.9700
C311—C312 1.514 (5) C714—C715 1.506 (5)
C312—N333 1.481 (4) C714—H71D 0.9700
C312—C313 1.528 (5) C714—H71E 0.9700
C312—H31A 0.9800 C715—O71C 1.197 (5)
N333—H33A 0.8900 C715—O71D 1.304 (5)
N333—H33B 0.8900 O71D—H7F 0.8200
N333—H33C 0.8900 O81A—C811 1.199 (5)
C313—C314 1.508 (6) O81B—C811 1.313 (5)
C313—H31B 0.9700 O81B—H8B 0.8200
C313—H31C 0.9700 C811—C812 1.521 (5)
C314—C315 1.507 (5) C812—N888 1.482 (5)
C314—H31D 0.9700 C812—C813 1.527 (5)
C314—H31E 0.9700 C812—H812 0.9800
C315—O31C 1.216 (5) N888—H88A 0.8900
C315—O31D 1.284 (5) N888—H88B 0.8900
O31D—H3F 0.8200 N888—H88C 0.8900
O41A—C411 1.197 (5) C813—C814 1.528 (5)
O41B—C411 1.317 (5) C813—H81A 0.9700
O41B—H4B 0.8200 C813—H81B 0.9700
C411—C412 1.518 (5) C814—C815 1.489 (5)
C412—N444 1.493 (5) C814—H81C 0.9700
C412—C413 1.533 (5) C814—H81D 0.9700
C412—H41A 0.9800 C815—O81C 1.183 (6)
N444—H44A 0.8900 C815—O81D 1.288 (6)
N444—H44B 0.8900 O81D—H8E 0.8200
N444—H44C 0.8900 OW1—H1WA 0.85 (6)
C413—C414 1.515 (5) OW1—H1WB 0.79 (6)
C413—H41B 0.9700 OW2—H2WA 0.81 (7)
C413—H41C 0.9700 OW2—H2WB 0.94 (8)
O11—S1—O13 113.0 (3) H41B—C413—H41C 107.8
O11—S1—O12 108.1 (2) C415—C414—C413 115.2 (3)
O13—S1—O12 110.2 (2) C415—C414—H41D 108.5
O11—S1—O14 107.6 (2) C413—C414—H41D 108.5
O13—S1—O14 105.4 (2) C415—C414—H41E 108.5
O12—S1—O14 112.48 (19) C413—C414—H41E 108.5
O21—S2—O22 109.7 (2) H41D—C414—H41E 107.5
O21—S2—O23 109.7 (2) O41C—C415—O41D 123.7 (3)
O22—S2—O23 109.7 (3) O41C—C415—C414 125.2 (3)
O21—S2—O24 110.34 (17) O41D—C415—C414 111.1 (3)
O23—S2—O24 107.82 (18) C511—O51B—H5B 109.5
O31—S3—O33 111.49 (18) O51A—C511—O51B 126.8 (4)
O31—S3—O32 110.60 (18) O51A—C511—C512 123.3 (3)
O33—S3—O32 108.29 (16) O51B—C511—C512 109.8 (3)
O31—S3—O34 107.75 (18) N555—C512—C511 109.3 (3)
O33—S3—O34 107.75 (17) N555—C512—C513 112.6 (3)
O32—S3—O34 110.94 (17) C511—C512—C513 111.0 (3)
O43—S4—O41 112.1 (2) N555—C512—H51A 107.9
O43—S4—O42 111.36 (19) C511—C512—H51A 107.9
O41—S4—O42 108.39 (19) C513—C512—H51A 107.9
O43—S4—O44 106.62 (18) C512—N555—H55A 109.5
O41—S4—O44 108.2 (2) C512—N555—H55B 109.5
O42—S4—O44 110.1 (2) H55A—N555—H55B 109.5
C111—O11B—H1B 109.5 C512—N555—H55C 109.5
O11A—C111—O11B 124.9 (4) H55A—N555—H55C 109.5
O11A—C111—C112 123.0 (4) H55B—N555—H55C 109.5
O11B—C111—C112 112.0 (3) C514—C513—C512 115.2 (3)
N111—C112—C111 108.8 (3) C514—C513—H51B 108.5
N111—C112—C113 112.0 (3) C512—C513—H51B 108.5
C111—C112—C113 116.3 (3) C514—C513—H51C 108.5
N111—C112—H112 106.4 C512—C513—H51C 108.5
C111—C112—H112 106.4 H51B—C513—H51C 107.5
C113—C112—H112 106.4 C515—C514—C513 113.8 (3)
C112—N111—H11A 109.5 C515—C514—H51D 108.8
C112—N111—H11B 109.5 C513—C514—H51D 108.8
H11A—N111—H11B 109.5 C515—C514—H51E 108.8
C112—N111—H11C 109.5 C513—C514—H51E 108.8
H11A—N111—H11C 109.5 H51D—C514—H51E 107.7
H11B—N111—H11C 109.5 O51C—C515—O51D 123.4 (3)
C114—C113—C112 113.9 (3) O51C—C515—C514 123.3 (3)
C114—C113—H11D 108.8 O51D—C515—C514 113.3 (3)
C112—C113—H11D 108.8 C515—O51D—H5F 109.5
C114—C113—H11E 108.8 C611—O61B—H6B 109.5
C112—C113—H11E 108.8 O61A—C611—O61B 124.7 (4)
H11D—C113—H11E 107.7 O61A—C611—C612 123.8 (3)
C113—C114—C115 111.5 (4) O61B—C611—C612 111.5 (3)
C113—C114—H11F 109.3 N666—C612—C611 108.2 (3)
C115—C114—H11F 109.3 N666—C612—C613 111.1 (3)
C113—C114—H11G 109.3 C611—C612—C613 111.7 (3)
C115—C114—H11G 109.3 N666—C612—H61A 108.6
H11F—C114—H11G 108.0 C611—C612—H61A 108.6
O11C—C115—O11D 122.1 (4) C613—C612—H61A 108.6
O11C—C115—C114 122.6 (4) C612—N666—H66A 109.5
O11D—C115—C114 115.3 (4) C612—N666—H66B 109.5
C115—O11D—H1H 109.5 H66A—N666—H66B 109.5
C211—O21B—H2B 109.5 C612—N666—H66C 109.5
O21A—C211—O21B 126.0 (4) H66A—N666—H66C 109.5
N222—C212—C211 109.2 (3) C614—C613—H61B 109.0
N222—C212—C213 107.3 (3) C612—C613—H61B 109.0
C211—C212—C213 110.8 (3) C614—C613—H61C 109.0
N222—C212—H21A 109.8 C612—C613—H61C 109.0
C211—C212—H21A 109.8 H61B—C613—H61C 107.8
C213—C212—H21A 109.8 C615—C614—C613 114.2 (3)
C212—N222—H22A 109.5 C615—C614—H61D 108.7
C212—N222—H22B 109.5 C613—C614—H61D 108.7
H22A—N222—H22B 109.5 C615—C614—H61E 108.7
C212—N222—H22C 109.5 C613—C614—H61E 108.7
H22A—N222—H22C 109.5 H61D—C614—H61E 107.6
H22B—N222—H22C 109.5 O61C—C615—O61D 124.0 (3)
C214—C213—C212 111.5 (4) O61C—C615—C614 124.2 (3)
C214—C213—H21B 109.3 O61D—C615—C614 111.9 (3)
C212—C213—H21B 109.3 C615—O61D—H6F 109.5
C214—C213—H21C 109.3 C711—O71B—H7B 109.5
C212—C213—H21C 109.3 O71A—C711—O71B 125.1 (4)
H21B—C213—H21C 108.0 O71A—C711—C712 124.1 (3)
C213—C214—C215 118.0 (5) O71B—C711—C712 110.8 (3)
C213—C214—H21D 107.8 N777—C712—C711 108.0 (3)
C215—C214—H21D 107.8 N777—C712—C713 113.2 (3)
C213—C214—H21E 107.8 C711—C712—C713 111.7 (3)
C215—C214—H21E 107.8 N777—C712—H71A 107.9
H21D—C214—H21E 107.1 C711—C712—H71A 107.9
O21C—C215—O21D 124.9 (4) C713—C712—H71A 107.9
O21C—C215—C214 119.3 (4) C712—N777—H77A 109.5
O21D—C215—C214 115.7 (4) C712—N777—H77B 109.5
C215—O21D—H2F 109.5 H77A—N777—H77B 109.5
C311—O31B—H3B 109.5 C712—N777—H77C 109.5
O31A—C311—O31B 124.8 (4) H77A—N777—H77C 109.5
O31A—C311—C312 123.4 (3) H77B—N777—H77C 109.5
O31B—C311—C312 111.8 (3) C714—C713—C712 113.8 (3)
N333—C312—C311 107.7 (3) C714—C713—H71B 108.8
N333—C312—C313 112.4 (3) C712—C713—H71B 108.8
C311—C312—C313 109.8 (3) C714—C713—H71C 108.8
N333—C312—H31A 109.0 C712—C713—H71C 108.8
C311—C312—H31A 109.0 H71B—C713—H71C 107.7
C313—C312—H31A 109.0 C715—C714—C713 115.4 (3)
C312—N333—H33A 109.5 C715—C714—H71D 108.4
C312—N333—H33B 109.5 C713—C714—H71D 108.4
H33A—N333—H33B 109.5 C715—C714—H71E 108.4
C312—N333—H33C 109.5 C713—C714—H71E 108.4
H33A—N333—H33C 109.5 H71D—C714—H71E 107.5
H33B—N333—H33C 109.5 O71C—C715—O71D 124.4 (3)
C314—C313—C312 114.3 (3) O71C—C715—C714 125.0 (3)
C314—C313—H31B 108.7 O71D—C715—C714 110.5 (3)
C314—C313—H31C 108.7 C811—O81B—H8B 109.5
C312—C313—H31C 108.7 O81A—C811—O81B 125.0 (4)
H31B—C313—H31C 107.6 O81A—C811—C812 123.9 (3)
C315—C314—C313 111.6 (3) O81B—C811—C812 111.0 (3)
C315—C314—H31D 109.3 N888—C812—C811 106.9 (3)
C313—C314—H31D 109.3 N888—C812—C813 113.2 (3)
C315—C314—H31E 109.3 C811—C812—C813 112.1 (3)
C313—C314—H31E 109.3 N888—C812—H812 108.1
H31D—C314—H31E 108.0 C811—C812—H812 108.1
O31C—C315—O31D 122.1 (3) C813—C812—H812 108.1
O31C—C315—C314 123.7 (4) C812—N888—H88A 109.5
O31D—C315—C314 114.2 (3) C812—N888—H88B 109.5
C315—O31D—H3F 109.5 H88A—N888—H88B 109.5
C411—O41B—H4B 109.5 C812—N888—H88C 109.5
O41A—C411—O41B 125.2 (4) H88A—N888—H88C 109.5
O41A—C411—C412 123.3 (3) H88B—N888—H88C 109.5
O41B—C411—C412 111.5 (3) C812—C813—C814 114.7 (3)
N444—C412—C411 108.5 (3) C812—C813—H81A 108.6
N444—C412—C413 112.9 (3) C814—C813—H81A 108.6
C411—C412—C413 111.5 (3) C812—C813—H81B 108.6
N444—C412—H41A 107.9 C814—C813—H81B 108.6
C411—C412—H41A 107.9 H81A—C813—H81B 107.6
C413—C412—H41A 107.9 C815—C814—C813 114.9 (3)
C412—N444—H44A 109.5 C815—C814—H81C 108.6
C412—N444—H44B 109.5 C813—C814—H81C 108.6
H44A—N444—H44B 109.5 C815—C814—H81D 108.6
C412—N444—H44C 109.5 C813—C814—H81D 108.6
H44A—N444—H44C 109.5 H81C—C814—H81D 107.5
H44B—N444—H44C 109.5 O81C—C815—O81D 122.0 (4)
C414—C413—C412 113.0 (3) O81C—C815—C814 124.2 (4)
C414—C413—H41B 109.0 O81D—C815—C814 113.8 (4)
C412—C413—H41B 109.0 C815—O81D—H8E 109.5
C414—C413—H41C 109.0 H1WA—OW1—H1WB 106 (5)
C412—C413—H41C 109.0 H2WA—OW2—H2WB 93 (6)
C211—C212—C213—C214 68.6 (6) C611—C612—C613—C614 −58.1 (4) C212—C213—C214—C215 −167.5 (7) C612—C613—C614—C615 −179.7 (3) C213—C214—C215—O21C −179.0 (7) C613—C614—C615—O61C −13.5 (5) C213—C214—C215—O21D −1.8 (11) C613—C614—C615—O61D 167.4 (3) O31A—C311—C312—N333 −16.3 (5) O71A—C711—C712—N777 −3.1 (5) O31B—C311—C312—N333 165.0 (3) O71B—C711—C712—N777 177.7 (3) O31A—C311—C312—C313 106.4 (4) O71A—C711—C712—C713 122.0 (4) O31B—C311—C312—C313 −72.4 (4) O71B—C711—C712—C713 −57.2 (4) N333—C312—C313—C314 −64.6 (4) N777—C712—C713—C714 72.2 (4) C311—C312—C313—C314 175.6 (3) C711—C712—C713—C714 −50.0 (4) C312—C313—C314—C315 −161.4 (3) C712—C713—C714—C715 168.9 (3) C313—C314—C315—O31C 49.6 (6) C713—C714—C715—O71C −22.9 (6) C313—C314—C315—O31D −129.7 (4) C713—C714—C715—O71D 159.9 (4) O41A—C411—C412—N444 −1.3 (5) O81A—C811—C812—N888 −7.9 (5) O41B—C411—C412—N444 179.9 (3) O81B—C811—C812—N888 173.5 (3) O41A—C411—C412—C413 123.7 (4) O81A—C811—C812—C813 116.8 (4) O41B—C411—C412—C413 −55.1 (4) O81B—C811—C812—C813 −61.9 (4) N444—C412—C413—C414 67.1 (4) N888—C812—C813—C814 72.0 (4) C411—C412—C413—C414 −55.3 (4) C811—C812—C813—C814 −49.1 (5) C412—C413—C414—C415 177.5 (3) C812—C813—C814—C815 173.0 (4) C413—C414—C415—O41C −19.5 (5) C813—C814—C815—O81C −6.8 (9) C413—C414—C415—O41D 161.5 (3) C813—C814—C815—O81D 172.8 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O11B—H1B···O21Ci 0.82 1.83 2.644 (4) 176
O21B—H2B···OW2ii 0.82 1.72 2.525 (5) 165
O31B—H3B···O51C 0.82 1.93 2.733 (4) 165
O41B—H4B···O71C 0.82 1.92 2.720 (4) 164
O51B—H5B···OW1 0.82 1.70 2.495 (4) 163
O61B—H6B···O41C 0.82 1.86 2.657 (4) 164
O71B—H7B···O11Ciii 0.82 1.78 2.591 (4) 169
O81B—H8B···O31Civ 0.82 1.81 2.625 (5) 177
O11D—H1H···O34v 0.82 1.77 2.585 (4) 173
O21D—H2F···O12vi 0.82 1.76 2.555 (4) 161
O31D—H3F···O14vii 0.82 1.81 2.604 (4) 162
O41D—H4F···O32 0.82 1.78 2.577 (4) 164
O51D—H5F···O41viii 0.82 1.78 2.595 (4) 172
O61D—H6F···O42iii 0.82 1.86 2.659 (4) 166
O71D—H7F···O33iii 0.82 1.86 2.625 (4) 155
O81D—H8E···O22i 0.82 2.20 2.958 (6) 153
O81D—H8E···O23i 0.82 2.39 3.081 (6) 142
N111—H11A···O24v 0.89 1.82 2.708 (4) 171
N111—H11B···O42viii 0.89 2.18 2.943 (5) 144
N111—H11C···O51C 0.89 2.13 2.998 (4) 164
N222—H22B···O44ix 0.89 1.95 2.801 (4) 160
N222—H22C···O51A 0.89 2.15 2.913 (4) 144
N222—H22C···O61Cviii 0.89 2.40 2.835 (4) 110
N333—H33A···O43 0.89 1.93 2.795 (4) 164
N333—H33A···O44 0.89 2.46 2.992 (4) 119
N333—H33B···O33 0.89 2.08 2.886 (4) 151
N333—H33B···O32 0.89 2.49 3.061 (4) 122
N333—H33C···O71Cv 0.89 2.34 3.070 (4) 139
N333—H33C···O41Av 0.89 2.36 3.036 (4) 133
N444—H44A···O14vii 0.89 1.92 2.804 (4) 172
N444—H44B···O23 0.89 1.94 2.797 (5) 161
N444—H44C···O21Ax 0.89 2.23 2.922 (4) 134
N555—H55A···O31vii 0.89 2.15 2.928 (4) 146
N555—H55A···O34vii 0.89 2.39 3.193 (4) 151
N555—H55B···O11ii 0.89 1.95 2.727 (5) 145
N555—H55C···O71Avii 0.89 2.41 3.095 (4) 134
N555—H55C···O11Cxi 0.89 2.48 3.056 (4) 123
N666—H66A···O34x 0.89 1.92 2.798 (4) 166
N666—H66A···O33x 0.89 2.59 3.254 (4) 132
N666—H66B···O13 0.89 2.02 2.844 (5) 154
N666—H66C···O21Cxii 0.89 2.03 2.807 (4) 145
N777—H77A···O13 0.89 2.20 2.962 (5) 143
N777—H77A···O14 0.89 2.21 2.992 (5) 147
N777—H77B···O22iv 0.89 1.97 2.830 (5) 162
N777—H77B···O21iv 0.89 2.62 3.084 (5) 114
N777—H77C···O31Civ 0.89 2.43 3.160 (5) 140
N888—H88A···O43 0.89 1.84 2.717 (4) 169
N888—H88B···O31 0.89 1.95 2.827 (4) 170
N888—H88C···O41C 0.89 2.40 3.084 (4) 134
N888—H88C···O61A 0.89 2.48 3.151 (4) 133
OW1—H1WA···O21 0.85 (6) 1.88 (6) 2.732 (4) 175 (5) OW1—H1WB···O61Cviii 0.79 (6) 2.07 (6) 2.803 (5) 155 (5) OW2—H2WA···O11 0.81 (7) 1.96 (7) 2.706 (5) 151 (6) OW2—H2WB···O81Ciii 0.94 (8) 1.78 (8) 2.725 (6) 174 (6)
Symmetry codes: (i) x, y+1, z−1; (ii) x−1, y−1, z; (iii) x, y, z+1; (iv) x, y+1, z; (v) x, y, z−1; (vi) x−1, y−1, z+1; (vii) x, y−1, z; (viii) x−1, y, z; (ix) x−1, y,
