organic papers
Acta Cryst.(2005). E61, o1283–o1285 doi:10.1107/S1600536805010305 Ohbaet al. C
8H12N+C14H13O3
o1283
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
(
R
)-1-Phenyl-1-ethylammonium (
R
)-2-hydroxymethyl-2-(2-naphthyl)propanoate
Shigeru Ohba,a* Tomomi Tsutsumi,bYosuke Terao,bKenji Miyamotoband Hiromichi Ohtab
aDepartment of Chemistry, Faculty of Letters,
Keio University, Hiyoshi 4-1-1, Kohoku-ku, Yokohama 223-8521, Japan, andbDepartment of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan
Correspondence e-mail: ohba@flet.keio.ac.jp
Key indicators
Single-crystal X-ray study T= 298 K
Mean(C–C) = 0.011 A˚ Disorder in main residue Rfactor = 0.048 wRfactor = 0.102 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 compound, C8H12N+C14H13O3, is the less soluble
diastereomeric salt of
2-hydroxymethyl-2-(2-naphthyl)-propanoic acid with (R)-(+)-phenylethylamine. The
ammo-nium group of the cation and the carboxylate group of the
anion are linked via N—H O hydrogen bonds, forming
ribbons along thebaxis.
Comment
Arylmalonate decarboxylase (AMDase) catalyzes the
enan-tioselective decarboxylation of arylmethylmalonic acid.
Recently, Ijima et al. (2005) have succeeded in preparing a
mutant enzyme of arylmalonate decarboxylase, which gives the opposite enantiomer compared with the product of the native enzyme. To investigate the stereochemical course of the reaction catalyzed by the mutant enzyme, both enantiomers of
methyl-2-naphthylmalonic acid, which contain 13C in either
one of the two carboxyl groups, were prepared.
The aim of the present paper is to assign the absolute configuration of the enantiomers of the
methyl-2-naphthyl-malonic acid labeled with 13C. The title compound, (I), is a
diastereomeric salt of the optically resolved synthetic inter-mediate 2-hydroxymethyl-2-(2-naphthyl)propanoic acid with phenylethylamine. An X-ray structure analysis of (I) has been carried out to determine the absolute configuration of (+)-2-hydroxymethyl-2-(2-naphthyl)propanoic acid based on the
known absolute configuration of (R)-(+)-phenylethylamine.
As shown in Fig. 1, compound (I) consists of organic ions as the result of deprotonation of the carboxylic acid group. All three H atoms of the ammonium group are involved in hydrogen bonding to the carboxylate group (Table 2). The
cations and anions are arranged alternately and connectedvia
N—H O hydrogen bonds to form ribbons that extend along
the baxis (Fig. 2). The crystals of (I) grown from methanol,
ethanol or aqueous solutions are fiber-like. As expected, the elongated direction of the needle specimen is thebaxis.
Experimental
()-2-Hydroxymethyl-2-(2-naphthyl)propanoic acid was prepared as described previously (Miyamotoet al., 1992). The optical resolution was carried out with (R)-(+)- phenylethylamine in acetone solution. The less soluble diastereomeric salts were recrystallized several times and dissolved in 2M NaOH solution, each enantiomer being extracted by ethyl acetate (94–98% enantiomeric excess). Compound (I) is the less soluble diastereomeric salt, which consists of (R)-(+)-phenylethylamine and (+)-2-hydroxymethyl-2-(2-naphthyl)-propanoic acid. The specific rotation, []D, of
(+)-2-hydroxymethyl-2-(2-naphthyl)propanoic acid at 293 K is +27.7 (1)(c= 1.0, EtOH,
wherecis a concentration of units grams per 100 cm3). Crystals of (I) suitable for X-ray study were grown from an aqueous solution by slow evaporation.
Crystal data
C8H12N+C14H13O3 Mr= 351.44
Monoclinic,P21 a= 12.791 (2) A˚ b= 6.4448 (16) A˚ c= 12.068 (3) A˚
= 104.741 (16)
V= 962.1 (4) A˚3 Z= 2
Dx= 1.213 Mg m
3
MoKradiation Cell parameters from 25
reflections
= 10.1–11.8
= 0.08 mm1 T= 298 K Needle, colorless 0.90.10.05 mm
Data collection
Rigaku AFC-7Rdiffractometer
!–2scans
Absorption correction: integration (ABSCOR; Higashi, 1999) Tmin= 0.992,Tmax= 0.996
2165 measured reflections 1854 independent reflections 698 reflections withI> 2(I)
Rint= 0.024 max= 25.0
h=6!15 k= 0!7 l=14!13 3 standard reflections
every 150 reflections intensity decay: none
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.048 wR(F2) = 0.102 S= 0.97 1854 reflections 244 parameters
H-atom parameters constrained w= 1/[2
(Fo2) + (0.0179P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.016
max= 0.16 e A˚3
min=0.19 e A˚3
Table 1
Selected geometric parameters (A˚ ,).
O1—C6 1.255 (9) O2—C6 1.280 (8)
O1—C6—C5—C9 106.1 (7)
O3A—C7—C5—C9 170.3 (6)
O3B—C7—C5—C9 57 (1)
N4—C20—C21—C26 51.3 (9)
C6—C5—C9—C10 40.6 (8)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O3A—H3A O1 0.95 2.07 2.743 (9) 126
O3B—H3B O3Ai
0.95 1.82 2.71 (2) 154
N4—H4A O1 0.95 1.84 2.769 (7) 166
N4—H4B O2ii
0.95 1.86 2.801 (6) 172
N4—H4C O2iii
0.95 1.85 2.791 (7) 172
Symmetry codes: (i)xþ1;þy1
2;z; (ii)x;þyþ 1
2;z; (iii)x;yþ1;z.
Due to the low scattering power of the crystal, only 38% of the measured reflections were observed. There is a positional disorder of the alcohol atom O3, the site occupation factors of O3Aand O3B being 70 and 30%, respectively. H atoms bonded to C atoms were positioned with idealized geometry and were refined with fixed isotropic displacement parameters [Uiso(H) = 1.2Ueq(C)] using a
organic papers
o1284
Ohbaet al. C [image:2.610.47.296.70.269.2]8H12N+C14H13O3 Acta Cryst.(2005). E61, o1283–o1285
Figure 1
Molecular structure of (I), with the atom-labeling scheme and displace-ment ellipsoids drawn at the 50% probability level. One of the two
possible positions of atom O3 has been omitted for clarity. Figure 2
riding model, with C—H = 0.95 A˚ . The positions of the N-bound H atoms were idealized on the basis of the position of one H atom, which was identified in a difference map. The O-bound H atoms were positioned with idealized geometry in the direction of the nearest appropriate hydrogen-bonding acceptor. The N- and O-bound H atoms were refined with fixed isotropic displacement parameters [Uiso(H) = 1.2Ueq(parent atom)] using a riding model with bond
distances of 0.95 A˚ . The absolute configuration was assigned on the basis of the known absolute configuration of (R )-(+)-phenylethyl-amine (Eliel, 1962; Nassimbeniet al., 1986). Because of negligible anomalous scattering effects, Friedel pairs were averaged in the refinement.
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction:TEXSAN(Molecular Structure Corpora-tion, 2001); program(s) used to solve structure:SIR92(Altomareet al., 1994); program(s) used to refine structure: SHELXL97 (Shel-drick, 1997); molecular graphics:ORTEPII(Johnson, 1976); software used to prepare material for publication:TEXSAN.
References
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994).J. Appl. Cryst.27, 435.
Eliel, E. L. (1962). Stereochemistry of Carbon Compounds. New York: McGraw-Hill.
Higashi, T. (1999).ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ijima, Y., Matoishi, K., Terao, Y., Doi, N., Yanagawa, H. & Ohta, H. (2005).J. Chem. Soc. Chem. Commun.pp. 877–879.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Nassimbeni, L. R., Niven, M. L. & Zemke, K. J. (1986).Acta Cryst.B42, 453– 461.
Miyamoto, K., Tsuchiya, S. & Ohta, H. (1992).J. Am. Chem. Soc.114, 6256– 6257.
Molecular Structure Corporation (2001).TEXSAN. Version 1.11. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.
Rigaku (1999).WinAFC Diffractometer Control Software. Rigaku Corpora-tion, Tokyo, Japan.
Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany.
organic papers
Acta Cryst.(2005). E61, o1283–o1285 Ohbaet al. C
supporting information
sup-1 Acta Cryst. (2005). E61, o1283–o1285
supporting information
Acta Cryst. (2005). E61, o1283–o1285 [https://doi.org/10.1107/S1600536805010305]
(
R
)-1-Phenyl-1-ethylammonium (
R
)-2-hydroxymethyl-2-(2-naphthyl)propanoate
Shigeru Ohba, Tomomi Tsutsumi, Yosuke Terao, Kenji Miyamoto and Hiromichi Ohta
(R)-1-Phenyl-1-ethylammonium (R)-2-hydroxymethyl-2-(2-naphthyl)propanoate
Crystal data
C8H12N+·C14H13O3−
Mr = 351.44
Monoclinic, P21
Hall symbol: P 2yb a = 12.791 (2) Å b = 6.4448 (16) Å c = 12.068 (3) Å β = 104.741 (16)° V = 962.1 (4) Å3
Z = 2
F(000) = 376 Dx = 1.213 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 10.1–11.8°
µ = 0.08 mm−1
T = 298 K Needle, colorless 0.9 × 0.1 × 0.05 mm
Data collection
Rigaku AFC-7R diffractometer ω–2θ scans
Absorption correction: integration (ABSCOR; Higashi, 1999) Tmin = 0.992, Tmax = 0.996
2165 measured reflections 1854 independent reflections
698 reflections with I > 2σ(I) Rint = 0.024
θmax = 25.0°
h = −6→15 k = 0→7 l = −14→13
3 standard reflections every 150 reflections intensity decay: none
Refinement
Refinement on F2
R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.102
S = 0.97 1854 reflections 244 parameters
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0179P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.016
Δρmax = 0.16 e Å−3
Δρmin = −0.19 e Å−3
Absolute structure: see text
Special details
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R
-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for
calculating R-factor (gt).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
supporting information
sup-2 Acta Cryst. (2005). E61, o1283–o1285
O2 0.1292 (3) −0.1683 (7) 0.0477 (3) 0.049 (1)
O3A 0.4034 (5) 0.088 (1) −0.0053 (6) 0.082 (3) 0.70 O3B 0.522 (1) −0.151 (3) 0.144 (2) 0.103 (7) 0.30 N4 0.0723 (4) 0.4311 (8) 0.0981 (4) 0.043 (1)
C5 0.3239 (5) −0.182 (1) 0.1008 (6) 0.042 (2) C6 0.2165 (6) −0.062 (1) 0.0704 (5) 0.038 (2) C7 0.4176 (5) −0.030 (1) 0.1003 (6) 0.061 (2) C8 0.3199 (5) −0.351 (1) 0.0109 (6) 0.063 (2) C9 0.3413 (5) −0.265 (1) 0.2237 (7) 0.051 (2) C10 0.3167 (5) −0.142 (1) 0.3064 (7) 0.051 (2) C11 0.3321 (6) −0.208 (1) 0.4203 (7) 0.058 (2) C12 0.3048 (6) −0.087 (1) 0.5040 (7) 0.070 (2) C13 0.3165 (6) −0.155 (2) 0.6126 (8) 0.085 (3) C14 0.3594 (7) −0.353 (2) 0.6449 (7) 0.086 (3) C15 0.3879 (7) −0.479 (2) 0.5663 (9) 0.084 (3) C16 0.3742 (6) −0.411 (1) 0.4509 (8) 0.056 (2) C17 0.4001 (6) −0.532 (1) 0.3665 (9) 0.070 (3) C18 0.3836 (6) −0.463 (1) 0.2566 (7) 0.059 (2) C19 0.0365 (7) 0.181 (1) 0.2359 (6) 0.076 (3) C20 0.0757 (5) 0.396 (1) 0.2216 (6) 0.051 (2) C21 0.0135 (5) 0.560 (1) 0.2682 (6) 0.048 (2) C22 0.0582 (5) 0.643 (1) 0.3732 (6) 0.053 (2) C23 −0.0007 (7) 0.777 (1) 0.4241 (6) 0.063 (2) C24 −0.1056 (7) 0.826 (1) 0.3710 (6) 0.067 (2) C25 −0.1506 (6) 0.745 (1) 0.2639 (7) 0.078 (3) C26 −0.0922 (6) 0.612 (2) 0.2137 (6) 0.071 (2)
H3A 0.3381 0.1653 −0.0189 0.0978* 0.70
H3B 0.5263 −0.2562 0.0899 0.1231* 0.30
H4A 0.1214 0.3393 0.0758 0.0517*
H4B 0.0012 0.4060 0.0524 0.0517*
H4C 0.0922 0.5704 0.0878 0.0517*
H7A1 0.4826 −0.1078 0.1119 0.0729* 0.70
H7A2 0.4235 0.0651 0.1618 0.0729* 0.70
H7B1 0.4155 0.0844 0.1494 0.0729* 0.30
H7B2 0.4121 0.0190 0.0248 0.0729* 0.30
H8A 0.2614 −0.4421 0.0099 0.0757*
H8B 0.3100 −0.2882 −0.0624 0.0757*
H8C 0.3858 −0.4264 0.0291 0.0757*
H10 0.2882 −0.0071 0.2858 0.0609*
H12 0.2770 0.0485 0.4844 0.0836*
H13 0.2955 −0.0690 0.6671 0.1022*
H14 0.3687 −0.3988 0.7216 0.1028*
H15 0.4169 −0.6128 0.5886 0.1009*
H17 0.4300 −0.6664 0.3858 0.0842*
H18 0.4011 −0.5512 0.2008 0.0707*
H19A −0.0362 0.1668 0.1920 0.0915*
H19B 0.0806 0.0829 0.2104 0.0915*
supporting information
sup-3 Acta Cryst. (2005). E61, o1283–o1285
H20 0.1492 0.4039 0.2641 0.0615*
H22 0.1304 0.6087 0.4122 0.0639*
H23 0.0323 0.8361 0.4967 0.0759*
H24 −0.1464 0.9142 0.4072 0.0809*
H25 −0.2224 0.7818 0.2244 0.0939*
H26 −0.1249 0.5542 0.1406 0.0847*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.052 (3) 0.034 (3) 0.070 (4) 0.004 (3) 0.015 (2) 0.006 (3) O2 0.033 (3) 0.044 (3) 0.065 (3) −0.005 (3) 0.004 (2) 0.005 (3) O3A 0.046 (4) 0.091 (7) 0.115 (6) −0.012 (5) 0.034 (4) 0.028 (6) O3B 0.07 (1) 0.09 (2) 0.15 (2) −0.03 (1) 0.04 (1) −0.04 (2) N4 0.039 (3) 0.032 (4) 0.061 (4) 0.003 (3) 0.017 (3) 0.002 (4) C5 0.032 (4) 0.038 (5) 0.062 (5) 0.001 (4) 0.022 (4) 0.001 (5) C6 0.043 (5) 0.042 (5) 0.032 (4) 0.016 (5) 0.014 (4) 0.001 (5) C7 0.045 (5) 0.050 (6) 0.089 (6) 0.002 (4) 0.020 (5) 0.008 (5) C8 0.061 (5) 0.050 (5) 0.082 (6) 0.003 (5) 0.025 (4) −0.013 (5) C9 0.031 (4) 0.035 (5) 0.086 (6) 0.006 (4) 0.014 (4) −0.001 (5) C10 0.043 (4) 0.042 (5) 0.066 (5) 0.011 (4) 0.012 (4) 0.001 (5) C11 0.040 (4) 0.064 (7) 0.068 (7) −0.015 (5) 0.013 (4) −0.015 (6) C12 0.067 (6) 0.081 (6) 0.055 (5) 0.006 (5) 0.003 (5) 0.001 (6) C13 0.057 (5) 0.13 (1) 0.069 (7) 0.002 (7) 0.015 (5) 0.004 (7) C14 0.059 (6) 0.124 (10) 0.067 (7) −0.004 (7) 0.004 (5) 0.044 (8) C15 0.062 (6) 0.094 (8) 0.089 (7) −0.006 (6) 0.006 (6) 0.015 (8) C16 0.046 (5) 0.044 (6) 0.073 (7) 0.004 (5) 0.007 (4) 0.011 (5) C17 0.057 (5) 0.045 (6) 0.097 (7) 0.009 (5) −0.001 (6) 0.011 (6) C18 0.050 (5) 0.042 (6) 0.079 (6) 0.015 (5) 0.006 (5) −0.001 (5) C19 0.118 (7) 0.040 (6) 0.086 (7) 0.016 (6) 0.054 (6) 0.022 (5) C20 0.050 (4) 0.056 (6) 0.048 (5) 0.007 (4) 0.013 (4) 0.009 (5) C21 0.053 (5) 0.047 (5) 0.047 (5) 0.002 (5) 0.019 (4) −0.005 (5) C22 0.062 (5) 0.057 (5) 0.042 (5) 0.004 (5) 0.016 (4) 0.015 (5) C23 0.081 (6) 0.059 (6) 0.053 (5) −0.004 (5) 0.023 (5) −0.003 (5) C24 0.084 (6) 0.053 (6) 0.073 (6) 0.005 (6) 0.033 (5) −0.008 (6) C25 0.044 (5) 0.102 (8) 0.087 (6) 0.025 (5) 0.013 (5) −0.010 (6) C26 0.046 (5) 0.092 (7) 0.064 (5) 0.007 (5) −0.003 (4) −0.023 (6)
Geometric parameters (Å, º)
O1—C6 1.255 (9) C12—H12 0.950
O2—C6 1.280 (8) C13—C14 1.40 (2)
O3A—C7 1.46 (1) C13—H13 0.950
O3A—H3A 0.950 C14—C15 1.37 (2)
O3B—C7 1.52 (2) C14—H14 0.950
O3B—H3B 0.950 C15—C16 1.43 (1)
N4—C20 1.497 (9) C15—H15 0.950
supporting information
sup-4 Acta Cryst. (2005). E61, o1283–o1285
N4—H4B 0.950 C17—C18 1.36 (1)
N4—H4C 0.950 C17—H17 0.950
C5—C6 1.539 (9) C18—H18 0.950
C5—C7 1.551 (10) C19—C20 1.50 (1)
C5—C8 1.53 (1) C19—H19A 0.950
C5—C9 1.54 (1) C19—H19B 0.950
C7—H7A1 0.950 C19—H19C 0.950
C7—H7A2 0.950 C20—C21 1.51 (1)
C7—H7B1 0.950 C20—H20 0.950
C7—H7B2 0.950 C21—C22 1.362 (10)
C8—H8A 0.950 C21—C26 1.386 (9)
C8—H8B 0.950 C22—C23 1.39 (1)
C8—H8C 0.950 C22—H22 0.950
C9—C10 1.37 (1) C23—C24 1.37 (1)
C9—C18 1.41 (1) C23—H23 0.950
C10—C11 1.40 (1) C24—C25 1.38 (1)
C10—H10 0.950 C24—H24 0.950
C11—C12 1.39 (1) C25—C26 1.38 (1)
C11—C16 1.42 (1) C25—H25 0.950
C12—C13 1.35 (1) C26—H26 0.950
C7—O3A—H3A 109.5 C12—C13—C14 120.2 (10)
C7—O3B—H3B 109.5 C12—C13—H13 119.9
C20—N4—H4A 109.5 C14—C13—H13 119.9
C20—N4—H4B 109.5 C13—C14—C15 120.1 (9)
C20—N4—H4C 109.5 C13—C14—H14 119.9
H4A—N4—H4B 109.5 C15—C14—H14 119.9
H4A—N4—H4C 109.5 C14—C15—C16 120.3 (9)
H4B—N4—H4C 109.5 C14—C15—H15 119.9
C6—C5—C7 108.8 (6) C16—C15—H15 119.9
C6—C5—C8 108.9 (5) C11—C16—C15 118.7 (9)
C6—C5—C9 107.8 (6) C11—C16—C17 118.1 (8)
C7—C5—C8 109.5 (6) C15—C16—C17 123.2 (8)
C7—C5—C9 107.4 (5) C16—C17—C18 121.4 (7)
C8—C5—C9 114.3 (6) C16—C17—H17 119.3
O1—C6—O2 123.2 (6) C18—C17—H17 119.3
O1—C6—C5 119.6 (6) C9—C18—C17 121.7 (8)
O2—C6—C5 117.2 (6) C9—C18—H18 119.1
O3A—C7—O3B 118.2 (10) C17—C18—H18 119.1
O3A—C7—C5 114.2 (5) C20—C19—H19A 109.5
O3A—C7—H7A1 108.3 C20—C19—H19B 109.5
O3A—C7—H7A2 108.3 C20—C19—H19C 109.5
O3B—C7—C5 106.6 (9) H19A—C19—H19B 109.5
O3B—C7—H7B1 110.2 H19A—C19—H19C 109.5
O3B—C7—H7B2 110.2 H19B—C19—H19C 109.5
C5—C7—H7A1 108.3 N4—C20—C19 109.2 (5)
C5—C7—H7A2 108.3 N4—C20—C21 112.3 (5)
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sup-5 Acta Cryst. (2005). E61, o1283–o1285
C5—C7—H7B2 110.2 C19—C20—C21 112.2 (6)
H7A1—C7—H7A2 109.5 C19—C20—H20 107.6
H7B1—C7—H7B2 109.5 C21—C20—H20 107.6
C5—C8—H8A 109.5 C20—C21—C22 119.0 (6)
C5—C8—H8B 109.5 C20—C21—C26 122.3 (6)
C5—C8—H8C 109.5 C22—C21—C26 118.3 (7)
H8A—C8—H8B 109.5 C21—C22—C23 120.7 (6)
H8A—C8—H8C 109.5 C21—C22—H22 119.6
H8B—C8—H8C 109.5 C23—C22—H22 119.6
C5—C9—C10 119.9 (6) C22—C23—C24 120.9 (6)
C5—C9—C18 122.5 (7) C22—C23—H23 119.5
C10—C9—C18 117.6 (8) C24—C23—H23 119.5
C9—C10—C11 122.4 (7) C23—C24—C25 118.6 (8)
C9—C10—H10 118.8 C23—C24—H24 120.7
C11—C10—H10 118.8 C25—C24—H24 120.7
C10—C11—C12 122.8 (8) C24—C25—C26 120.3 (7)
C10—C11—C16 118.8 (8) C24—C25—H25 119.8
C12—C11—C16 118.3 (8) C26—C25—H25 119.8
C11—C12—C13 122.3 (9) C21—C26—C25 121.1 (6)
C11—C12—H12 118.8 C21—C26—H26 119.5
C13—C12—H12 118.8 C25—C26—H26 119.5
supporting information
sup-6 Acta Cryst. (2005). E61, o1283–o1285
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O3A—H3A···O1 0.95 2.07 2.743 (9) 126
O3B—H3B···O3Ai 0.95 1.82 2.71 (2) 154
N4—H4A···O1 0.95 1.84 2.769 (7) 166
N4—H4B···O2ii 0.95 1.86 2.801 (6) 172
N4—H4C···O2iii 0.95 1.85 2.791 (7) 172
