organic papers
Acta Cryst.(2005). E61, o2987–o2989 doi:10.1107/S1600536805025870 Muthamizhchelvanet al. C
6H16N+C6H2N3O7
o2987
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Triethylaminium picrate
Chellamuthu
Muthamizhchelvan,a Kolandaivelu Saminathan,b Krishnan SethuSankar,bJan Fraanje,cRene Pescharcand Kandasamy Sivakumarb*
aDepartment of Physics, SRM Engineering
College, Kattankulathur 603 203, India,
bDepartment of Physics, Anna University,
Chennai 600 025, India, andcLaboratory of
Crystallography, Institute of Molecular Chemistry, University of Amsterdam, Achtergracht 116, 1018 WV, Amsterdam, The Netherlands
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 293 K
Mean(C–C) = 0.009 A˚ Rfactor = 0.052 wRfactor = 0.165 Data-to-parameter ratio = 7.6
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The title salt, C6H16N +
C6H2N3O7
, crystallizes with two pairs of cations and anions in the asymmetric unit. AnionsAandB
are stacked alternately in the (020) plane to form anionic columns having anABABAB. . . sequence, with possible–
interactions between them. The cationic columns surround these columns in an almost hexagonal fashion, with each column of the same type of cation, A orB. The anions and cations are connected through lone N—H O and by other C—H O hydrogen bonds. N—H O and C—H O hydrogen bonds involving A-and B- type ions form a cyclic pattern with a graph-set descriptorR2
2
(10).
Comment
Picric acid forms crystalline picrates with various organic molecules and such picrates are convenient for identification and qualitative analysis of organic compounds. The formation of picrates is a common method for the conversion of liquids into stable, tractable solid compounds (Takayanagi et al., 1996). Crystal structures of a large number of picrate salts and picric acid complexes, including the biological base molecules, have been studied in the past (Nagataet al., 1995; Smithet al., 2004; Goto et al., 2004). In many cases, the bonding of these electron-donor picric acid complexes depends stronglyon the nature of the partner. The linkage could involve not only electrostatic attraction, but also the formation of molecular complexes (Zaderenko et al., 1997). The title salt, (I), was prepared to study the nature and directionality of the specific N—H O hydrogen bond involving the protonated N atom and factors influencing the tilting of the nitro groups of the picrate ion in the solid state.
The asymmetric unit of (I) contains two sets of picrate anions and triethylaminium cations. The picrate anions lie almost parallel to each other, with a dihedral angle of 8.3 (1),
but have different orientations. These ions lie on (020) planes in an alternate fashion. The triethylaminium cations take up suitable orientations to produce N—H O hydrogen bonds between the ions (Fig. 1).
The partial double-bond character of C1—O1 and length-ening of the C1—C2 and C1—C6 bonds from the regular aromatic values around C1 may be attributed to the loss of the
hydroxyl proton at O1 for anions A and B, leading to the conversion from the neutral to the anionic state of the picrate molecules, as observed in other picrate salts (Mutha-mizhchelvan et al., 2005, 2005a). This also suggests charge delocalization around atom C1.
The twist angles of the three nitro groups from the benzene plane of the picrate ion are 37.0 (3) (O2—N1—O3), 3.1 (4) (O4—N2—O5) and 37.7 (3)(O6—N3—O7) for picrate anion A, and 37.9 (4), 3.0 (4) and 40.4 (4)for anionB. An analysis
of the tilting of the nitro groups in picrate ions shows that the
ortho-nitro groups, in general, deviate away from the benzene plane due to steric interactions with the phenol group at C1, but thepara-nitro groups lie in the benzene plane. Deviations from this normal tilting behaviour arise in many structures as a result of crystal packing criteria which involve N—H O and C—H O hydrogen bonds or short contacts with the nitro group O atoms (Muthamizhchelvan et al., 2005b). In the present structure, however, the nitro-group orientations are normal in nature.
AnionsAandBare stacked alternately in a plane parallel to the crystallographic (020) plane. The stacking leads to the formation of anionic columns having an ABABAB. . . sequence, with possible – interactions, as the anions are separated by 3.486 A˚ . The cationic columns surround these columns in an almost hexagonal manner, with each column of the same type of cation,AorB. This columnar stacking of the anions along thebaxis is shown in Fig. 2. The intermolecular contacts between the anion and cation include the character-istic N—H O and extensive C—H O hydrogen bonds (Table 2). The positioning of cations facilitates the formation of N4—H4 O1, which is stronger and linear, as expected. Apart from this, the linear alignment of two of the three ethyl groups of the cation leads to the formation of C10—H10 O2 and C12—H12 O7 hydrogen bonds in ionic pairB, but only C10—H10 O2 between the A ions; C12A—H12A O7A
has longer H A (3.406 A˚ ) and C O (3.976 A˚ ) distances, and hence could not be classified as a C—H O hydrogen
bond. CationBconnects the two anions by N4B—H4B O1B
and C9B—H9D O4Ahydrogen bonds, with the C—H O bond making the link along thebaxis. C12B—H12D O4B
connects the B type anions and cations, and this link is nearly parallel to the a axis. No such linking is found among the ions of type A. The N—H O and C—H O hydrogen bonds involving A-type ions form a cyclic pattern with a graph-set descriptor R22(10), viz.
N4A—H4A O1A—C1A—C2A—N1A—O2A H10B— C10A—C9A, whereas ions of type B form two such cyclic patterns with motifs N4B—H4B O1B—C1B—C2B— N1B—O2B H10F—C10B—C9B and N4B—H4B O1B— C1B—C6B—N3B—O7B H12E—C12B—C11B (Fig. 1) (Bernsteinet al., 1995).
Experimental
Crystals of (I) were prepared from an ethanol solution containing equimolar amounts of picric acid and triethylamine at room temperature. Yellow pyramid-shaped single crystals were obtained by slow evaporation of the ethanol solution.
Crystal data
C6H16N+C6H2N3O7
Mr= 330.30
Orthorhombic,Pca21
a= 21.9799 (15) A˚
b= 6.9727 (4) A˚
c= 20.7700 (13) A˚
V= 3183.2 (3) A˚3
Z= 8
Dx= 1.378 Mg m
3
CuKradiation Cell parameters from 25
reflections
= 15–50 = 0.98 mm1
T= 293 (2) K Pyramid, yellow 0.50.40.3 mm
Data collection
Enraf–Nonius CAD-4 diffractometer
!–2scans
Absorption correction: scan (Northet al., 1968)
Tmin= 0.682,Tmax= 0.745
3634 measured reflections 3363 independent reflections 2403 reflections withI> 2(I)
Rint= 0.057
max= 74.7
h=8!27
k=3!8
l=8!25 2 standard reflections
every 100 reflections intensity decay: 1%
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Muthamizhchelvanet al. C [image:2.610.45.296.71.244.2]6H16N+C6H2N3O7 Acta Cryst.(2005). E61, o2987–o2989
Figure 1
A 30% displacement ellipsoid plot of the title salt, showing the atom-numbering scheme. Both sets of cations and anions present in the asymmetric unit are shown. Dashed lines indicate the hydrogen bonds within each set of ions.
Figure 2
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.052
wR(F2) = 0.165
S= 1.02 3363 reflections 440 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2
(Fo2) + (0.1004P)2
+ 0.2349P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.27 e A˚
3 min=0.18 e A˚
3
Extinction correction:SHELXL97
Extinction coefficient: 0.0009 (2)
Table 1
Selected geometric parameters (A˚ ,).
O1A—C1A 1.234 (5) C1A—C2A 1.450 (5) C1A—C6A 1.454 (6) N4A—C9A 1.444 (8) N4A—C7A 1.477 (8) N4A—C11A 1.487 (13)
O1B—C1B 1.250 (5) C1B—C6B 1.431 (7) C1B—C2B 1.441 (6) N4B—C11B 1.495 (6) N4B—C7B 1.502 (7) N4B—C9B 1.519 (7) O1A—C1A—C2A 123.5 (4)
O1A—C1A—C6A 124.8 (4) C2A—C1A—C6A 111.5 (3)
O1B—C1B—C6B 125.0 (4) O1B—C1B—C2B 123.4 (4) C6B—C1B—C2B 111.5 (3) C11A—N4A—C9A—C10A166.1 (11)
C9A—N4A—C11A—C12A 171.9 (7)
C11B—N4B—C9B—C10B 173.2 (5) C9B—N4B—C11B—C12B179.3 (5)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N4A—H4A O1A 1.01 (7) 1.76 (7) 2.767 (5) 172 (5) N4B—H4B O1B 1.00 (8) 1.82 (8) 2.781 (5) 160 (7) C10A—H10B O2A 0.96 2.42 3.307 (13) 154 C10B—H10F O2B 0.96 2.53 3.483 (9) 170 C12B—H12E O7B 0.96 2.64 3.258 (10) 123 C7A—H7A O5Bi
0.97 2.65 3.584 (7) 162 C8A—H8C O5Aii 0.96 2.68 3.448 (10) 137 C10A—H10A O6Aii
0.96 2.61 3.547 (14) 166 C11A—H11B O4Biii
0.97 2.62 3.265 (9) 124 C12A—H12A O6Biv
0.96 2.62 3.553 (11) 163 C7B—H7C O4Av
0.97 2.60 3.454 (7) 147 C9B—H9D O4Avi
0.97 2.44 3.336 (8) 154 C12B—H12D O4Bvii
0.96 2.58 3.496 (8) 160
Symmetry codes: (i) xþ1;yþ1;z1
2; (ii) xþ 1 2;y;zþ
1 2; (iii)
xþ1;yþ2;z1
2; (iv) xþ 1 2;yþ1;z
1
2; (v) xþ1;yþ1;zþ 1 2; (vi)
xþ1;yþ2;zþ1 2; (vii)x
1 2;yþ1;z.
The H atoms were located in difference maps. While the H atoms of the three ethyl group were made to ride (C—H = 0.93–0.96 A˚ ) on their respective C atoms, the other H atoms were refined isotropically. For CH2H atoms,Uiso(H) values were set equal to 1.2Ueq(C) and for
the methyl H atoms they were set at 1.5Ueq(C). In the absence of
significant anomalous dispersion effects, Friedel pairs were averaged. Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1997); cell refinement:CAD-4 EXPRESS; data reduction:XCAD4(Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3(Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication:SHELXL97.
The authors thank Professor H. Schenk, Laboratory of Crystallography, Institute of Molecular Chemistry, University of Amsterdam, for his encouragement and help in data collection.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995).Angew. Chem. Int. Ed. Engl.34, 1555–1573.
Enraf–Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf–Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Goto, M., Kanno, H., Sugaya, E., Osa, Y. & Takayanagi, H. (2004).Anal. Sci.
20, x39–x40.
Harms, K. & Wocadlo, S. (1995).XCAD4.University of Marburg, Germany. Muthamizhchelvan, C., Saminathan, K., Fraanje, J., Peschar, R. & Sivakumar,
K. (2005).Anal. Sci.21, x61–x62.
Muthamizhchelvan, C., Saminathan, K., SethuSankar, K., Fraanje, J., Peschar, R. & Sivakumar, K. (2005a).Acta Cryst.E61, o1377–o1380.
Muthamizhchelvan, C., Saminathan, K., SethuSankar, K., Fraanje, J., Peschar, R. & Sivakumar, K. (2005b).Acta Cryst.E61, o1546–o1548.
Nagata, H., In, Y., Doi, M., Ishida, T. & Wakahara, A. (1995).Acta Cryst.B51, 1051–1058.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351– 359.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Smith, G., Wermuth, U. D. & Healy, P. C. (2004).Acta Cryst.E60, o1800– o1803.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
Takayanagi, H., Kai, T., Yamaguchi, S., Takeda, K. & Goto, M. (1996).Chem. Pharm. Bull.44, 2199–2204.
Zaderenko, P., Gil, M. S., Lopez, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997).Acta Cryst.B53, 961–967.
organic papers
Acta Cryst.(2005). E61, o2987–o2989 Muthamizhchelvanet al. C
supporting information
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Acta Cryst. (2005). E61, o2987–o2989
supporting information
Acta Cryst. (2005). E61, o2987–o2989 [https://doi.org/10.1107/S1600536805025870]
Triethylaminium picrate
Chellamuthu Muthamizhchelvan, Kolandaivelu Saminathan, Krishnan SethuSankar, Jan Fraanje,
Rene Peschar and Kandasamy Sivakumar
Triethylaminium picrate
Crystal data
C6H16N+·C6H2N3O7−
Mr = 330.30
Orthorhombic, Pca21 Hall symbol: P 2c -2ac
a = 21.9799 (15) Å
b = 6.9727 (4) Å
c = 20.7700 (13) Å
V = 3183.2 (3) Å3
Z = 8
F(000) = 1392
Dx = 1.378 Mg m−3
Cu Kα radiation, λ = 1.54178 Å Cell parameters from 25 reflections
θ = 15–50°
µ = 0.98 mm−1
T = 293 K Pyramidal, yellow 0.5 × 0.4 × 0.3 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 = 0.682, Tmax = 0.745 3634 measured reflections
3363 independent reflections 2403 reflections with I > 2σ(I)
Rint = 0.057
θmax = 74.7°, θmin = 4.0°
h = −8→27
k = −3→8
l = −8→25
2 standard reflections every 100 reflections intensity decay: 1%
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.052
wR(F2) = 0.165
S = 1.02 3363 reflections 440 parameters 3 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(F
o2) + (0.1004P)2 + 0.2349P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.27 e Å−3 Δρmin = −0.18 e Å−3
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Acta Cryst. (2005). E61, o2987–o2989
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
O1A 0.27755 (14) 0.9469 (6) 0.40260 (17) 0.0799 (9)
O2A 0.3783 (2) 0.8759 (8) 0.4768 (2) 0.1118 (15)
O3A 0.44675 (19) 1.0764 (7) 0.4429 (2) 0.0972 (12)
O4A 0.50171 (18) 0.9438 (7) 0.2210 (2) 0.1016 (13)
O5A 0.4305 (2) 0.8915 (8) 0.15120 (19) 0.1101 (14)
O6A 0.2197 (2) 0.9545 (10) 0.2250 (3) 0.1254 (18)
O7A 0.20470 (17) 0.7831 (8) 0.3094 (3) 0.1168 (15)
N1A 0.40325 (19) 0.9697 (7) 0.4339 (2) 0.0727 (10)
N2A 0.4485 (2) 0.9209 (6) 0.2065 (2) 0.0790 (11)
N3A 0.2370 (2) 0.8766 (7) 0.2741 (2) 0.0809 (11)
C1A 0.31536 (17) 0.9291 (5) 0.3591 (2) 0.0552 (9)
C2A 0.38041 (18) 0.9473 (5) 0.3690 (2) 0.0554 (9)
C3A 0.42253 (18) 0.9504 (5) 0.3202 (2) 0.0569 (9)
C4A 0.4028 (2) 0.9259 (6) 0.2577 (2) 0.0615 (10)
C5A 0.3426 (2) 0.9042 (6) 0.2426 (2) 0.0622 (10)
C6A 0.30067 (18) 0.9031 (6) 0.2914 (2) 0.0576 (9)
N4A 0.17041 (19) 0.9221 (8) 0.4721 (2) 0.0895 (14)
C7A 0.1472 (3) 0.7256 (9) 0.4619 (3) 0.0944 (16)
H7A 0.1798 0.6353 0.4704 0.113*
H7B 0.1356 0.7115 0.4171 0.113*
C8A 0.0928 (4) 0.6739 (12) 0.5042 (4) 0.124 (3)
H8A 0.0803 0.5447 0.4952 0.186*
H8B 0.0598 0.7600 0.4953 0.186*
H8C 0.1041 0.6844 0.5487 0.186*
C9A 0.1930 (5) 0.981 (2) 0.5343 (4) 0.252 (11)
H9A 0.1611 0.9571 0.5656 0.302*
H9B 0.1994 1.1184 0.5329 0.302*
C10A 0.2494 (6) 0.892 (3) 0.5588 (5) 0.284 (12)
H10A 0.2565 0.9329 0.6022 0.426*
H10B 0.2831 0.9292 0.5322 0.426*
H10C 0.2453 0.7545 0.5579 0.426*
C11A 0.1246 (5) 1.0724 (11) 0.4570 (8) 0.163 (5)
H11A 0.0910 1.0613 0.4870 0.196*
H11B 0.1430 1.1975 0.4631 0.196*
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H12A 0.0710 1.1598 0.3836 0.287*
H12B 0.0814 0.9374 0.3840 0.287*
H12C 0.1332 1.0746 0.3601 0.287*
O1B 0.54679 (15) 0.5403 (6) 0.72140 (19) 0.0860 (10)
O2B 0.6359 (3) 0.6909 (11) 0.6415 (2) 0.146 (2)
O3B 0.7158 (3) 0.5304 (12) 0.6599 (3) 0.147 (2)
O4B 0.78537 (14) 0.6353 (6) 0.8795 (2) 0.0921 (11)
O5B 0.72258 (18) 0.5833 (8) 0.9564 (2) 0.1003 (13)
O6B 0.5116 (2) 0.4255 (8) 0.9027 (3) 0.1154 (16)
O7B 0.47849 (17) 0.6244 (9) 0.8318 (3) 0.1257 (18)
N1B 0.6679 (2) 0.6027 (7) 0.6778 (2) 0.0826 (12)
N2B 0.73400 (17) 0.6036 (6) 0.8994 (2) 0.0708 (10)
N3B 0.51909 (17) 0.5309 (7) 0.8561 (3) 0.0842 (13)
C1B 0.58816 (19) 0.5621 (6) 0.7620 (2) 0.0597 (9)
C6B 0.58025 (17) 0.5511 (6) 0.8303 (2) 0.0599 (10)
C5B 0.62663 (19) 0.5578 (6) 0.8749 (2) 0.0587 (10)
C4B 0.68484 (17) 0.5855 (6) 0.8535 (2) 0.0564 (9)
C3B 0.69780 (19) 0.6014 (6) 0.7880 (2) 0.0598 (10)
C2B 0.65117 (19) 0.5894 (6) 0.7451 (2) 0.0584 (9)
N4B 0.43620 (15) 0.5500 (6) 0.65648 (18) 0.0671 (10)
C7B 0.4329 (3) 0.3752 (9) 0.6143 (3) 0.0932 (17)
H7C 0.4344 0.2614 0.6411 0.112*
H7D 0.4680 0.3729 0.5861 0.112*
C8B 0.3746 (4) 0.3706 (14) 0.5734 (4) 0.131 (3)
H8D 0.3746 0.2577 0.5469 0.196*
H8E 0.3731 0.4825 0.5465 0.196*
H8F 0.3397 0.3686 0.6012 0.196*
C9B 0.4404 (2) 0.7359 (9) 0.6186 (3) 0.0889 (15)
H9C 0.4031 0.7521 0.5944 0.107*
H9D 0.4432 0.8415 0.6489 0.107*
C10B 0.4921 (3) 0.7482 (14) 0.5738 (4) 0.120 (2)
H10D 0.4912 0.8697 0.5521 0.180*
H10E 0.4893 0.6466 0.5427 0.180*
H10F 0.5295 0.7363 0.5974 0.180*
C11B 0.3868 (2) 0.5622 (9) 0.7058 (3) 0.0862 (16)
H11C 0.3951 0.6697 0.7341 0.103*
H11D 0.3485 0.5872 0.6842 0.103*
C12B 0.3806 (3) 0.3875 (13) 0.7449 (4) 0.113 (2)
H12D 0.3490 0.4055 0.7762 0.170*
H12E 0.4183 0.3616 0.7666 0.170*
H12F 0.3704 0.2813 0.7176 0.170*
H3A 0.468 (3) 0.960 (8) 0.324 (3) 0.095 (18)*
H5A 0.3294 (19) 0.873 (6) 0.199 (2) 0.055 (11)*
H4A 0.209 (3) 0.918 (9) 0.446 (3) 0.094 (18)*
H3B 0.617 (2) 0.537 (7) 0.918 (2) 0.061 (12)*
H5B 0.737 (3) 0.630 (8) 0.768 (3) 0.083 (16)*
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Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1A 0.0612 (17) 0.109 (3) 0.0691 (19) 0.0074 (16) 0.0189 (15) −0.0032 (19)
O2A 0.098 (3) 0.166 (4) 0.072 (2) 0.004 (3) 0.001 (2) 0.035 (3)
O3A 0.085 (2) 0.120 (3) 0.087 (3) −0.015 (2) −0.022 (2) −0.002 (2)
O4A 0.069 (2) 0.127 (4) 0.108 (3) 0.000 (2) 0.034 (2) 0.005 (3)
O5A 0.121 (3) 0.145 (4) 0.065 (2) 0.020 (3) 0.031 (2) −0.003 (2)
O6A 0.087 (3) 0.193 (5) 0.096 (3) 0.013 (3) −0.024 (2) 0.008 (3)
O7A 0.068 (2) 0.155 (4) 0.127 (3) −0.037 (2) 0.001 (2) 0.012 (3)
N1A 0.062 (2) 0.091 (3) 0.065 (2) 0.0123 (19) −0.0019 (17) 0.009 (2)
N2A 0.084 (3) 0.082 (3) 0.071 (3) 0.008 (2) 0.026 (2) 0.005 (2)
N3A 0.069 (2) 0.093 (3) 0.080 (3) −0.002 (2) −0.005 (2) −0.009 (2)
C1A 0.0514 (19) 0.050 (2) 0.064 (2) 0.0033 (15) 0.0049 (17) 0.0018 (17)
C2A 0.0522 (19) 0.053 (2) 0.061 (2) 0.0035 (15) 0.0042 (16) 0.0043 (18)
C3A 0.0495 (19) 0.054 (2) 0.067 (2) 0.0057 (15) 0.0105 (18) 0.0013 (18)
C4A 0.069 (2) 0.052 (2) 0.064 (2) 0.0063 (17) 0.016 (2) 0.0039 (18)
C5A 0.073 (3) 0.056 (2) 0.058 (2) 0.0047 (19) 0.004 (2) −0.0027 (19)
C6A 0.0535 (19) 0.054 (2) 0.065 (2) 0.0014 (16) 0.0031 (17) −0.0051 (19)
N4A 0.061 (2) 0.127 (4) 0.080 (3) −0.011 (2) 0.025 (2) −0.021 (3)
C7A 0.102 (4) 0.091 (4) 0.090 (3) 0.016 (3) 0.020 (3) 0.006 (3)
C8A 0.140 (6) 0.112 (5) 0.120 (5) −0.035 (4) 0.028 (5) 0.011 (4)
C9A 0.181 (11) 0.46 (3) 0.115 (7) −0.177 (15) 0.082 (8) −0.124 (12)
C10A 0.136 (9) 0.63 (4) 0.087 (6) −0.020 (16) 0.018 (6) 0.053 (12)
C11A 0.127 (7) 0.079 (4) 0.284 (15) −0.011 (4) 0.125 (9) −0.016 (6)
C12A 0.081 (5) 0.154 (9) 0.34 (2) 0.017 (5) 0.008 (8) 0.094 (12)
O1B 0.0656 (18) 0.103 (3) 0.090 (2) −0.0009 (17) −0.0277 (18) 0.002 (2)
O2B 0.141 (4) 0.218 (7) 0.081 (3) 0.011 (4) −0.008 (3) 0.045 (4)
O3B 0.128 (4) 0.225 (7) 0.087 (3) 0.025 (4) 0.024 (3) −0.002 (4)
O4B 0.0517 (17) 0.121 (3) 0.103 (3) −0.0057 (17) −0.0094 (17) −0.014 (2)
O5B 0.082 (2) 0.147 (4) 0.072 (2) 0.001 (2) −0.0132 (18) 0.003 (2)
O6B 0.087 (3) 0.135 (4) 0.125 (4) −0.016 (2) 0.030 (3) 0.017 (3)
O7B 0.0568 (19) 0.170 (4) 0.150 (4) 0.023 (2) −0.005 (2) −0.012 (4)
N1B 0.085 (3) 0.097 (3) 0.066 (2) −0.002 (2) −0.004 (2) 0.000 (2)
N2B 0.064 (2) 0.074 (2) 0.074 (3) 0.0040 (17) −0.0172 (19) −0.007 (2)
N3B 0.052 (2) 0.094 (3) 0.106 (3) −0.004 (2) 0.001 (2) −0.016 (3)
C1B 0.056 (2) 0.052 (2) 0.071 (2) 0.0059 (16) −0.0130 (18) −0.0016 (19)
C6B 0.0483 (18) 0.054 (2) 0.077 (3) 0.0035 (15) −0.0006 (18) 0.001 (2)
C5B 0.059 (2) 0.054 (2) 0.064 (2) −0.0014 (16) −0.0027 (18) 0.0037 (19)
C4B 0.0489 (18) 0.050 (2) 0.071 (2) 0.0039 (15) −0.0075 (17) −0.0014 (17)
C3B 0.054 (2) 0.054 (2) 0.071 (3) −0.0009 (17) −0.0029 (19) −0.0013 (19)
C2B 0.059 (2) 0.052 (2) 0.064 (2) 0.0016 (16) −0.0046 (18) 0.0019 (18)
N4B 0.0489 (16) 0.097 (3) 0.0549 (18) 0.0111 (17) −0.0060 (14) −0.0012 (19)
C7B 0.099 (4) 0.103 (4) 0.078 (3) 0.033 (3) −0.005 (3) −0.007 (3)
C8B 0.146 (7) 0.146 (7) 0.100 (5) −0.005 (5) −0.029 (5) −0.046 (5)
C9B 0.086 (3) 0.094 (4) 0.087 (3) 0.008 (3) −0.015 (3) −0.002 (3)
C10B 0.085 (4) 0.169 (7) 0.107 (4) −0.022 (4) −0.013 (3) 0.047 (5)
supporting information
sup-5
Acta Cryst. (2005). E61, o2987–o2989
C12B 0.081 (4) 0.162 (7) 0.096 (4) −0.005 (4) 0.015 (3) 0.021 (4)
Geometric parameters (Å, º)
O1A—C1A 1.234 (5) O1B—C1B 1.250 (5)
O2A—N1A 1.233 (6) O2B—N1B 1.200 (7)
O3A—N1A 1.226 (6) O3B—N1B 1.227 (7)
O4A—N2A 1.219 (6) O4B—N2B 1.222 (5)
O5A—N2A 1.232 (6) O5B—N2B 1.218 (6)
O6A—N3A 1.217 (7) O6B—N3B 1.226 (7)
O7A—N3A 1.210 (6) O7B—N3B 1.215 (7)
N1A—C2A 1.447 (6) N1B—C2B 1.447 (7)
N2A—C4A 1.463 (6) N2B—C4B 1.447 (5)
N3A—C6A 1.457 (6) N3B—C6B 1.454 (6)
C1A—C2A 1.450 (5) C1B—C6B 1.431 (7)
C1A—C6A 1.454 (6) C1B—C2B 1.441 (6)
C2A—C3A 1.373 (6) C6B—C5B 1.379 (6)
C3A—C4A 1.378 (7) C5B—C4B 1.369 (6)
C3A—H3A 1.00 (6) C5B—H3B 0.93 (5)
C4A—C5A 1.368 (7) C4B—C3B 1.393 (6)
C5A—C6A 1.371 (6) C3B—C2B 1.362 (6)
C5A—H5A 0.97 (5) C3B—H5B 0.97 (6)
N4A—C9A 1.444 (8) N4B—C11B 1.495 (6)
N4A—C7A 1.477 (8) N4B—C7B 1.502 (7)
N4A—C11A 1.487 (13) N4B—C9B 1.519 (7)
N4A—H4A 1.01 (7) N4B—H4B 1.00 (8)
C7A—C8A 1.526 (9) C7B—C8B 1.539 (9)
C7A—H7A 0.9700 C7B—H7C 0.9700
C7A—H7B 0.9700 C7B—H7D 0.9700
C8A—H8A 0.9600 C8B—H8D 0.9600
C8A—H8B 0.9600 C8B—H8E 0.9600
C8A—H8C 0.9600 C8B—H8F 0.9600
C9A—C10A 1.479 (10) C9B—C10B 1.471 (9)
C9A—H9A 0.9700 C9B—H9C 0.9700
C9A—H9B 0.9700 C9B—H9D 0.9700
C10A—H10A 0.9600 C10B—H10D 0.9600
C10A—H10B 0.9600 C10B—H10E 0.9600
C10A—H10C 0.9600 C10B—H10F 0.9600
C11A—C12A 1.49 (2) C11B—C12B 1.470 (10)
C11A—H11A 0.9700 C11B—H11C 0.9700
C11A—H11B 0.9700 C11B—H11D 0.9700
C12A—H12A 0.9600 C12B—H12D 0.9600
C12A—H12B 0.9600 C12B—H12E 0.9600
C12A—H12C 0.9600 C12B—H12F 0.9600
O3A—N1A—O2A 123.9 (5) O2B—N1B—O3B 121.5 (6)
O3A—N1A—C2A 118.6 (4) O2B—N1B—C2B 119.4 (5)
supporting information
sup-6
Acta Cryst. (2005). E61, o2987–o2989
O4A—N2A—O5A 124.0 (4) O5B—N2B—O4B 122.7 (4)
O4A—N2A—C4A 118.4 (5) O5B—N2B—C4B 118.4 (4)
O5A—N2A—C4A 117.6 (5) O4B—N2B—C4B 118.9 (4)
O7A—N3A—O6A 124.4 (5) O7B—N3B—O6B 123.4 (5)
O7A—N3A—C6A 118.9 (5) O7B—N3B—C6B 118.3 (6)
O6A—N3A—C6A 116.8 (5) O6B—N3B—C6B 118.2 (5)
O1A—C1A—C2A 123.5 (4) O1B—C1B—C6B 125.0 (4)
O1A—C1A—C6A 124.8 (4) O1B—C1B—C2B 123.4 (4)
C2A—C1A—C6A 111.5 (3) C6B—C1B—C2B 111.5 (3)
C3A—C2A—N1A 116.9 (4) C5B—C6B—C1B 125.1 (4)
C3A—C2A—C1A 124.2 (4) C5B—C6B—N3B 116.1 (4)
N1A—C2A—C1A 118.9 (4) C1B—C6B—N3B 118.9 (4)
C2A—C3A—C4A 118.7 (4) C4B—C5B—C6B 118.5 (4)
C2A—C3A—H3A 127 (4) C4B—C5B—H3B 123 (3)
C4A—C3A—H3A 114 (4) C6B—C5B—H3B 118 (3)
C5A—C4A—C3A 122.3 (4) C5B—C4B—C3B 121.4 (4)
C5A—C4A—N2A 119.6 (4) C5B—C4B—N2B 119.7 (4)
C3A—C4A—N2A 118.1 (4) C3B—C4B—N2B 118.9 (4)
C4A—C5A—C6A 118.7 (4) C2B—C3B—C4B 118.7 (4)
C4A—C5A—H5A 122 (3) C2B—C3B—H5B 113 (4)
C6A—C5A—H5A 119 (3) C4B—C3B—H5B 128 (4)
C5A—C6A—C1A 124.4 (4) C3B—C2B—C1B 124.8 (4)
C5A—C6A—N3A 117.7 (4) C3B—C2B—N1B 116.0 (4)
C1A—C6A—N3A 117.8 (4) C1B—C2B—N1B 119.2 (4)
C9A—N4A—C7A 120.6 (8) C11B—N4B—C7B 114.3 (4)
C9A—N4A—C11A 102.8 (9) C11B—N4B—C9B 110.5 (4)
C7A—N4A—C11A 112.9 (5) C7B—N4B—C9B 113.2 (4)
C9A—N4A—H4A 102 (4) C11B—N4B—H4B 110 (5)
C7A—N4A—H4A 101 (3) C7B—N4B—H4B 96 (5)
C11A—N4A—H4A 118 (4) C9B—N4B—H4B 113 (5)
N4A—C7A—C8A 114.0 (5) N4B—C7B—C8B 112.3 (5)
N4A—C7A—H7A 108.7 N4B—C7B—H7C 109.1
C8A—C7A—H7A 108.7 C8B—C7B—H7C 109.1
N4A—C7A—H7B 108.7 N4B—C7B—H7D 109.1
C8A—C7A—H7B 108.7 C8B—C7B—H7D 109.1
H7A—C7A—H7B 107.6 H7C—C7B—H7D 107.9
C7A—C8A—H8A 109.5 C7B—C8B—H8D 109.5
C7A—C8A—H8B 109.5 C7B—C8B—H8E 109.5
H8A—C8A—H8B 109.5 H8D—C8B—H8E 109.5
C7A—C8A—H8C 109.5 C7B—C8B—H8F 109.5
H8A—C8A—H8C 109.5 H8D—C8B—H8F 109.5
H8B—C8A—H8C 109.5 H8E—C8B—H8F 109.5
N4A—C9A—C10A 118.5 (10) C10B—C9B—N4B 115.1 (5)
N4A—C9A—H9A 107.7 C10B—C9B—H9C 108.5
C10A—C9A—H9A 107.7 N4B—C9B—H9C 108.5
N4A—C9A—H9B 107.7 C10B—C9B—H9D 108.5
C10A—C9A—H9B 107.7 N4B—C9B—H9D 108.5
supporting information
sup-7
Acta Cryst. (2005). E61, o2987–o2989
C9A—C10A—H10A 109.5 C9B—C10B—H10D 109.5
C9A—C10A—H10B 109.5 C9B—C10B—H10E 109.5
H10A—C10A—H10B 109.5 H10D—C10B—H10E 109.5
C9A—C10A—H10C 109.5 C9B—C10B—H10F 109.5
H10A—C10A—H10C 109.5 H10D—C10B—H10F 109.5
H10B—C10A—H10C 109.5 H10E—C10B—H10F 109.5
C12A—C11A—N4A 113.4 (8) C12B—C11B—N4B 113.5 (5)
C12A—C11A—H11A 108.9 C12B—C11B—H11C 108.9
N4A—C11A—H11A 108.9 N4B—C11B—H11C 108.9
C12A—C11A—H11B 108.9 C12B—C11B—H11D 108.9
N4A—C11A—H11B 108.9 N4B—C11B—H11D 108.9
H11A—C11A—H11B 107.7 H11C—C11B—H11D 107.7
C11A—C12A—H12A 109.5 C11B—C12B—H12D 109.5
C11A—C12A—H12B 109.5 C11B—C12B—H12E 109.5
H12A—C12A—H12B 109.5 H12D—C12B—H12E 109.5
C11A—C12A—H12C 109.5 C11B—C12B—H12F 109.5
H12A—C12A—H12C 109.5 H12D—C12B—H12F 109.5
H12B—C12A—H12C 109.5 H12E—C12B—H12F 109.5
O3A—N1A—C2A—C3A 35.3 (6) O1B—C1B—C6B—C5B 173.8 (4)
O2A—N1A—C2A—C3A −143.1 (4) C2B—C1B—C6B—C5B −2.4 (6)
O3A—N1A—C2A—C1A −142.8 (4) O1B—C1B—C6B—N3B −6.1 (7)
O2A—N1A—C2A—C1A 38.8 (6) C2B—C1B—C6B—N3B 177.7 (4)
O1A—C1A—C2A—C3A −172.0 (4) O7B—N3B—C6B—C5B 138.8 (5)
C6A—C1A—C2A—C3A 3.4 (5) O6B—N3B—C6B—C5B −38.6 (7)
O1A—C1A—C2A—N1A 6.0 (6) O7B—N3B—C6B—C1B −41.3 (7)
C6A—C1A—C2A—N1A −178.6 (4) O6B—N3B—C6B—C1B 141.3 (5)
N1A—C2A—C3A—C4A 178.8 (4) C1B—C6B—C5B—C4B 3.0 (6)
C1A—C2A—C3A—C4A −3.2 (6) N3B—C6B—C5B—C4B −177.1 (4)
C2A—C3A—C4A—C5A 1.9 (6) C6B—C5B—C4B—C3B −1.8 (6)
C2A—C3A—C4A—N2A −177.3 (4) C6B—C5B—C4B—N2B 176.6 (4)
O4A—N2A—C4A—C5A 178.8 (4) O5B—N2B—C4B—C5B 3.9 (7)
O5A—N2A—C4A—C5A −2.0 (7) O4B—N2B—C4B—C5B −177.4 (4)
O4A—N2A—C4A—C3A −2.0 (6) O5B—N2B—C4B—C3B −177.7 (4)
O5A—N2A—C4A—C3A 177.3 (5) O4B—N2B—C4B—C3B 1.1 (6)
C3A—C4A—C5A—C6A −1.3 (6) C5B—C4B—C3B—C2B 0.2 (6)
N2A—C4A—C5A—C6A 177.9 (4) N2B—C4B—C3B—C2B −178.2 (4)
C4A—C5A—C6A—C1A 1.8 (7) C4B—C3B—C2B—C1B 0.4 (7)
C4A—C5A—C6A—N3A −179.0 (4) C4B—C3B—C2B—N1B −178.7 (4)
O1A—C1A—C6A—C5A 172.6 (4) O1B—C1B—C2B—C3B −175.6 (4)
C2A—C1A—C6A—C5A −2.7 (6) C6B—C1B—C2B—C3B 0.7 (6)
O1A—C1A—C6A—N3A −6.6 (6) O1B—C1B—C2B—N1B 3.4 (6)
C2A—C1A—C6A—N3A 178.1 (4) C6B—C1B—C2B—N1B 179.6 (4)
O7A—N3A—C6A—C5A 143.2 (5) O2B—N1B—C2B—C3B −140.7 (6)
O6A—N3A—C6A—C5A −38.2 (7) O3B—N1B—C2B—C3B 36.1 (8)
O7A—N3A—C6A—C1A −37.6 (7) O2B—N1B—C2B—C1B 40.3 (7)
O6A—N3A—C6A—C1A 141.1 (5) O3B—N1B—C2B—C1B −142.9 (6)
supporting information
sup-8
Acta Cryst. (2005). E61, o2987–o2989
C11A—N4A—C7A—C8A −61.5 (9) C9B—N4B—C7B—C8B −64.5 (7)
C7A—N4A—C9A—C10A 67.1 (11) C11B—N4B—C9B—C10B 173.2 (5)
C11A—N4A—C9A—C10A −166.1 (11) C7B—N4B—C9B—C10B −57.1 (6)
C9A—N4A—C11A—C12A 171.9 (7) C7B—N4B—C11B—C12B 51.7 (6)
C7A—N4A—C11A—C12A −56.6 (8) C9B—N4B—C11B—C12B −179.3 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N4A—H4A···O1A 1.01 (7) 1.76 (7) 2.767 (5) 172 (5)
N4B—H4B···O1B 1.00 (8) 1.82 (8) 2.781 (5) 160 (7)
C10A—H10B···O2A 0.96 2.42 3.307 (13) 154
C10B—H10F···O2B 0.96 2.53 3.483 (9) 170
C12B—H12E···O7B 0.96 2.64 3.258 (10) 123
C7A—H7A···O5Bi 0.97 2.65 3.584 (7) 162
C8A—H8C···O5Aii 0.96 2.68 3.448 (10) 137
C10A—H10A···O6Aii 0.96 2.61 3.547 (14) 166
C11A—H11B···O4Biii 0.97 2.62 3.265 (9) 124
C12A—H12A···O6Biv 0.96 2.62 3.553 (11) 163
C7B—H7C···O4Av 0.97 2.60 3.454 (7) 147
C9B—H9D···O4Avi 0.97 2.44 3.336 (8) 154
C12B—H12D···O4Bvii 0.96 2.58 3.496 (8) 160
