organic papers
o3190
Chruszczet al. C7H15NO4S doi:10.1107/S1600536805027728 Acta Cryst.(2005). E61, o3190–o3191
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
3-(Morpholinium-1-yl)propanesulfonate
Maksymilian Chruszcz,aHeping Zheng,aMarcin Cymborowski,a Anna Gawlicka-Chruszczband Wladek Minora*
aUniversity of Virginia, Department of Molecular
Physiology and Biological Physics, 1300 Jefferson Park Avenue, Charlottesville, VA 22908, USA, andbHKL Research Inc., 310 Old Ivy Way, Charlottesville, VA 22903, USA
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 103 K
Mean(C–C) = 0.001 A˚ Rfactor = 0.026 wRfactor = 0.075
Data-to-parameter ratio = 18.5
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 crystal structure of the title compound, C7H15NO4S, was determined at 103 K. There are two molecules in the asymmetric unit with different conformations of the aliphatic chains. In the solid state, the title molecule is a zwitterion.
Comment
The introduction of sulfonic compounds as zwitterionic buffers, e.g. MES [2-(N-morpholino)ethanesulfonic acid], MOPS [3-(N-morpholino)propanesulfonic acid] and HEPES {[4-(2-hydroxyethyl)-1-piperazine]ethanesulfonic acid}, has allowed better study of many biological processes (Goodet al., 1966; Good & Izawa, 1972; Fergusonet al., 1980). The crystal structures of MES, its sodium salt (Christensen et al., 1993; Deschampset al.2002) and HEPES (Wouterset al., 1996) have already been reported. In this paper, the crystal structure of MOPS, (I), is presented. Different conformations of the propanesulfonate chain in the two molecules of the asym-metric unit are illustrated by their torsion angles (Table 1).
The title compound is zwitterionic in the crystal structure, as is also observed in the structures of MES monohydrate and of HEPES. The N atoms are protonated, as confirmed by loca-tion of the H atoms in a difference Fourier map. Both N atoms are proton donors in N—H O intermolecular hydrogen bonds (Table 2). Hydrogen bonds occur only between mol-ecules with different conformations of the aliphatic chains. There are also short contacts between O atoms of the sulfonic groups (O2a, O2band O3a) and C atoms (C3a, C4a, C7aand C7b), with O C distances ranging from 3.139 to 3.401 A˚ and O H—C angles greater than 150. Both morpholine rings have chair conformations.
Experimental
3-(N-Morpholino)propanesulfonic acid was purchased from FLUKA. The crystal of (I) for data collection was obtained at room temperature by slow evaporation of 1MMOPS solution in water.
Crystal data
C7H15NO4S Mr= 209.26
Monoclinic,P21=c a= 6.149 (1) A˚
b= 11.255 (1) A˚
c= 27.402 (1) A˚
= 90.431 (1) V= 1896.4 (4) A˚3
Z= 8
Dx= 1.466 Mg m3
MoKradiation
Cell parameters from 12720 reflections
= 2.3–32.0
= 0.33 mm1 T= 103 (2) K Plate, colourless 0.100.100.02 mm
Data collection
Rigaku R-AXIS RAPID diffractometer
!scans withoffset
Absorption correction: multi-scan (Otwinowskiet al., 2003)
Tmin= 0.958,Tmax= 0.994
12720 measured reflections
6578 independent reflections 5857 reflections withI> 2(I)
Rint= 0.012
max= 32.0 h=9!9
k=16!16
l=40!40
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.026
wR(F2) = 0.075 S= 1.06 6578 reflections 355 parameters
All H-atom parameters refined
w= 1/[2(F
o2) + (0.0397P)2
+ 0.5917P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001 max= 0.45 e A˚3 min=0.41 e A˚3
Table 1
Selected torsion angles ().
N1b—C3b—C2b—C1b 177.97 (7) N1a—C3a—C2a—C1a 60.82 (10) C3b—C2b—C1b—S1b 175.84 (6)
C3a—C2a—C1a—S1a 173.62 (6) C4a—N1a—C3a—C2a 176.19 (7) C4b—N1b—C3b—C2b 177.91 (7)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N1a—H0a O4b 0.89 (1) 1.84 (1) 2.7227 (10) 174 (1) N1b—H0b O3ai
0.88 (1) 1.92 (1) 2.7871 (10) 171 (1)
Symmetry code: (i)x1;y;z.
Data collection: HKL2000 (Otwinowski & Minor, 1997); cell refinement:HKL2000; data reduction:HKL2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) and HKL2000; program(s) used to refine structure: SHELXL97(Sheldrick, 1997) andHKL2000; molecular graphics:HKL2000,ORTEPIII(Burnett & Johnson, 1996),ORTEP3(Farrugia, 1997) and O (Joneset al., 1991); software used to prepare material for publication: HKL2000 and SHELXL97.
This work was supported by contract GI11496 from HKL Research, Inc. The authors thank Rigaku/MSC for the loan of the RAPID diffractometer system.
References
Burnett, M. N. & Johnson, C. K. (1996).ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Christensen, A. N., Hazell, R. G., Lehman, M. S. & Nielsen, M. (1993).Acta Chem. Scand.47, 753–756.
Deschamps, J. R., Flippen-Anderson, J. L. & Clifford, G. (2002).Acta Cryst.
E58, m167–m168.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Ferguson, W. J., Braunschweiger, K. I., Braunschweiger, W. R., Smith, J. R., McCormick, J. J., Wasmann, C. C., Jarvis, N. P., Bell, D. H. & Good, N. E. (1980).Anal. Biochem.104, 300–10.
Good, N. E. & Izawa, S. (1972).Methods Enzymol.24, 53–68.
Good, N. E., Winget, G. D., Winter, W., Connolly, T. N., Izawa, S. & Singh, R. M. (1966).Biochemistry,5, 467-477.
Jones, T. A., Zou, J. Y., Cowan, S. W. & Kjeldgaard, M. (1991).Acta Cryst.A47, 110–119.
Otwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003).Acta Cryst.A59, 228–234.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Sheldrick, G. M. (1990).Acta Cryst.A46, 467–473.
[image:2.610.342.544.71.306.2]Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Wouters, J., Ha¨ming, L. & Sheldrick, G. (1996).Acta Cryst.C52, 1687–1688.
Figure 1
supporting information
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Acta Cryst. (2005). E61, o3190–o3191supporting information
Acta Cryst. (2005). E61, o3190–o3191 [doi:10.1107/S1600536805027728]
3-(Morpholinium-1-yl)propanesulfonate
Maksymilian Chruszcz, Heping Zheng, Marcin Cymborowski, Anna Gawlicka-Chruszcz and
Wladek Minor
S1. Comment
The introduction of sulfonic compounds as zwitterionic buffers, e.g. MES [2-(N-morpholino)ethanesulfonic acid], MOPS
[3-(N-morpholino)propanesulfonic acid] and HEPES {[4-(2-hydroxyethyl)-1-piperazine]ethanesulfonic acid}, has
allowed for better study of many biological processes (Good et al., 1966; Good & Izawa, 1972; Ferguson et al., 1980).
The crystal structures of MES, its sodium salt (Christensen et al., 1993; Deschamps et al. 2002) and HEPES (Wouters et
al., 1996) have already been reported. In this paper the crystal structure of MOPS, (I), is presented. Different
conformations of the propanesulfonate moiety are illustrated by their torsion angles (Table 1).
The title compound is zwitterionic in the crystal, which is also observed in the structures of MES monohydrate and of
HEPES. The N atoms are protonated, as confirmed by localization of the H atoms from the difference Fourier map. Both
N atoms are proton donors in N—H···O intermolecular hydrogen bonds (Table 2). Hydrogen bonds occur only between
molecules with different conformations of the aliphatic chains. There are also short contacts between O atoms of the
sulfonic groups (O2A, O2B and O3A) and C atoms (C3A, C4A, C7A and C7B), with O···C distances ranging from 3.139
to 3.401 Å and O···H—C angles greater than 150°. Both morpholine rings have a chair conformation.
S2. Experimental
3-(N-Morpholino)propanesulfonic acid was purchased from FLUKA. The crystal of (I) for data collection was obtained
Figure 1
The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as
spheres of arbitrary radii.
3-(morpholinium-1-yl)propanesulfonate
Crystal data
C7H15NO4S Mr = 209.26 Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 6.149 (1) Å
b = 11.255 (1) Å
c = 27.402 (1) Å
β = 90.431 (1)°
V = 1896.4 (4) Å3
Z = 8
F(000) = 896
Dx = 1.466 Mg m−3
Mo Kα radiation, λ = 0.71074 Å
Cell parameters from 12720 reflections
θ = 2.3–32.0°
µ = 0.33 mm−1
T = 103 K
supporting information
sup-3
Acta Cryst. (2005). E61, o3190–o3191Data collection
Goniostat vertical Euler diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 10.0 pixels mm-1
ω scan with χ offset
Absorption correction: multi-scan (Otwinowski et al., 2003)
Tmin = 0.958, Tmax = 0.994
12720 measured reflections 6578 independent reflections 5857 reflections with I > 2σ(I)
Rint = 0.012
θmax = 32.0°, θmin = 2.3°
h = −9→9
k = −16→16
l = −40→40
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.026 wR(F2) = 0.075
S = 1.06
6578 reflections 355 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map All H-atom parameters refined
w = 1/[σ2(Fo2) + (0.0397P)2 + 0.5917P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.45 e Å−3
Δρmin = −0.41 e Å−3
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
S1A 0.28275 (3) 0.717987 (18) 0.323707 (7) 0.01242 (5)
N1A 0.26199 (12) 0.29656 (6) 0.30120 (3) 0.01186 (12)
H0A 0.166 (2) 0.3149 (13) 0.3240 (5) 0.021 (3)*
O1A 0.44217 (11) 0.07792 (6) 0.33722 (2) 0.01749 (12)
O2A 0.24359 (11) 0.77974 (6) 0.27776 (2) 0.01646 (12)
O3A 0.51595 (11) 0.71193 (6) 0.33608 (2) 0.01723 (12)
O4A 0.15499 (12) 0.76277 (6) 0.36412 (3) 0.02138 (14)
C1A 0.19910 (14) 0.56788 (7) 0.31482 (3) 0.01455 (15)
H1A 0.219 (2) 0.5306 (12) 0.3454 (5) 0.021 (3)*
H2A 0.044 (2) 0.5714 (13) 0.3080 (5) 0.025 (3)*
C2A 0.32582 (15) 0.50907 (7) 0.27378 (3) 0.01489 (15)
H3A 0.306 (2) 0.5547 (12) 0.2445 (5) 0.021 (3)*
H4A 0.482 (2) 0.5061 (11) 0.2815 (5) 0.017 (3)*
C3A 0.24752 (15) 0.38543 (7) 0.26013 (3) 0.01453 (14)
H5A 0.096 (2) 0.3853 (12) 0.2497 (5) 0.019 (3)*
C4A 0.19435 (15) 0.17706 (7) 0.28183 (3) 0.01552 (15)
H7A 0.284 (2) 0.1629 (12) 0.2547 (5) 0.019 (3)*
H8A 0.046 (2) 0.1848 (12) 0.2722 (5) 0.017 (3)*
C5A 0.22253 (15) 0.08175 (8) 0.32037 (4) 0.01824 (16)
H9A 0.186 (2) 0.0038 (12) 0.3062 (5) 0.020 (3)*
H10A 0.126 (2) 0.0981 (12) 0.3476 (5) 0.020 (3)*
C6A 0.49529 (15) 0.18802 (8) 0.36034 (3) 0.01627 (15)
H11A 0.640 (2) 0.1825 (12) 0.3725 (5) 0.020 (3)*
H12A 0.397 (2) 0.2020 (12) 0.3876 (5) 0.019 (3)*
C7A 0.48440 (14) 0.29011 (8) 0.32430 (3) 0.01461 (15)
H13A 0.510 (2) 0.3633 (12) 0.3401 (5) 0.022 (3)*
H14A 0.587 (2) 0.2807 (12) 0.2988 (5) 0.021 (3)*
S1B 0.01299 (3) 0.349348 (18) 0.422149 (7) 0.01249 (5)
N1B −0.41309 (11) 0.75543 (6) 0.43506 (3) 0.01211 (12)
H0B −0.448 (2) 0.7468 (12) 0.4041 (5) 0.022 (3)*
O1B −0.42816 (11) 1.00877 (6) 0.44656 (2) 0.01616 (12)
O2B 0.00990 (12) 0.23599 (6) 0.44759 (3) 0.02099 (14)
O3B 0.21427 (10) 0.41650 (6) 0.42900 (2) 0.01785 (13)
O4B −0.04555 (10) 0.33849 (6) 0.37006 (2) 0.01573 (12)
C1B −0.19955 (14) 0.43603 (8) 0.44803 (3) 0.01436 (14)
H1B −0.170 (2) 0.4383 (12) 0.4822 (5) 0.020 (3)*
H2B −0.332 (2) 0.3943 (12) 0.4427 (5) 0.020 (3)*
C2B −0.20932 (14) 0.56177 (8) 0.42706 (3) 0.01557 (15)
H3B −0.073 (2) 0.5985 (13) 0.4310 (5) 0.024 (3)*
H4B −0.243 (2) 0.5591 (14) 0.3932 (6) 0.033 (4)*
C3B −0.38412 (14) 0.63126 (7) 0.45404 (3) 0.01381 (14)
H5B −0.522 (2) 0.5948 (12) 0.4501 (5) 0.017 (3)*
H6B −0.354 (2) 0.6381 (12) 0.4886 (5) 0.019 (3)*
C4B −0.59290 (13) 0.81659 (8) 0.46206 (3) 0.01424 (14)
H7B −0.548 (2) 0.8196 (13) 0.4967 (5) 0.021 (3)*
H8B −0.724 (2) 0.7690 (12) 0.4576 (5) 0.021 (3)*
C5B −0.62333 (14) 0.94128 (8) 0.44211 (3) 0.01570 (15)
H9B −0.731 (2) 0.9786 (12) 0.4617 (5) 0.019 (3)*
H10B −0.673 (2) 0.9373 (12) 0.4081 (5) 0.017 (3)*
C6B −0.25831 (14) 0.95341 (8) 0.41978 (3) 0.01586 (15)
H11B −0.132 (2) 1.0008 (12) 0.4229 (5) 0.018 (3)*
H12B −0.297 (2) 0.9489 (12) 0.3850 (5) 0.019 (3)*
C7B −0.21014 (13) 0.82933 (8) 0.43872 (3) 0.01424 (14)
H13B −0.107 (2) 0.7956 (12) 0.4190 (5) 0.017 (3)*
H14B −0.164 (2) 0.8293 (11) 0.4723 (5) 0.013 (3)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
S1A 0.01428 (9) 0.01221 (9) 0.01078 (9) −0.00151 (6) 0.00090 (7) −0.00072 (6)
N1A 0.0130 (3) 0.0105 (3) 0.0121 (3) 0.0007 (2) 0.0001 (2) −0.0005 (2)
O1A 0.0196 (3) 0.0127 (3) 0.0201 (3) 0.0030 (2) −0.0036 (2) −0.0001 (2)
supporting information
sup-5
Acta Cryst. (2005). E61, o3190–o3191O3A 0.0150 (3) 0.0210 (3) 0.0156 (3) −0.0015 (2) −0.0026 (2) −0.0002 (2)
O4A 0.0238 (3) 0.0213 (3) 0.0192 (3) −0.0039 (3) 0.0083 (3) −0.0069 (3)
C1A 0.0185 (4) 0.0119 (3) 0.0132 (4) −0.0019 (3) 0.0023 (3) 0.0007 (3)
C2A 0.0186 (4) 0.0120 (3) 0.0142 (4) −0.0003 (3) 0.0028 (3) 0.0012 (3)
C3A 0.0197 (4) 0.0120 (3) 0.0118 (3) 0.0009 (3) −0.0003 (3) 0.0013 (3)
C4A 0.0181 (4) 0.0111 (3) 0.0173 (4) 0.0001 (3) −0.0034 (3) −0.0018 (3)
C5A 0.0204 (4) 0.0124 (3) 0.0219 (4) −0.0016 (3) −0.0040 (3) 0.0018 (3)
C6A 0.0181 (4) 0.0148 (3) 0.0159 (4) 0.0010 (3) −0.0027 (3) 0.0010 (3)
C7A 0.0132 (3) 0.0142 (3) 0.0164 (4) −0.0001 (3) −0.0017 (3) 0.0008 (3)
S1B 0.01312 (9) 0.01215 (9) 0.01219 (9) 0.00111 (6) 0.00092 (6) 0.00083 (6)
N1B 0.0124 (3) 0.0134 (3) 0.0104 (3) 0.0015 (2) 0.0006 (2) −0.0006 (2)
O1B 0.0169 (3) 0.0140 (3) 0.0175 (3) 0.0009 (2) 0.0006 (2) −0.0025 (2)
O2B 0.0266 (3) 0.0149 (3) 0.0216 (3) 0.0044 (2) 0.0039 (3) 0.0059 (2)
O3B 0.0134 (3) 0.0208 (3) 0.0193 (3) −0.0009 (2) −0.0016 (2) −0.0010 (2)
O4B 0.0151 (3) 0.0197 (3) 0.0125 (3) 0.0003 (2) 0.0008 (2) −0.0020 (2)
C1B 0.0156 (3) 0.0137 (3) 0.0137 (4) 0.0013 (3) 0.0032 (3) 0.0008 (3)
C2B 0.0170 (4) 0.0141 (3) 0.0156 (4) 0.0030 (3) 0.0043 (3) 0.0022 (3)
C3B 0.0152 (3) 0.0127 (3) 0.0136 (4) 0.0017 (3) 0.0023 (3) 0.0009 (3)
C4B 0.0127 (3) 0.0154 (3) 0.0146 (4) 0.0023 (3) 0.0025 (3) −0.0013 (3)
C5B 0.0150 (3) 0.0149 (3) 0.0172 (4) 0.0027 (3) −0.0006 (3) −0.0016 (3)
C6B 0.0163 (3) 0.0148 (3) 0.0165 (4) 0.0008 (3) 0.0019 (3) 0.0012 (3)
C7B 0.0119 (3) 0.0157 (3) 0.0151 (4) −0.0002 (3) 0.0004 (3) 0.0003 (3)
Geometric parameters (Å, º)
S1A—O4A 1.4529 (7) S1B—O2B 1.4540 (7)
S1A—O2A 1.4567 (7) S1B—O3B 1.4610 (7)
S1A—O3A 1.4726 (7) S1B—O4B 1.4744 (7)
S1A—C1A 1.7822 (9) S1B—C1B 1.7823 (9)
N1A—C4A 1.5034 (11) N1B—C3B 1.5014 (11)
N1A—C7A 1.5044 (11) N1B—C4B 1.5020 (11)
N1A—C3A 1.5078 (11) N1B—C7B 1.5025 (11)
N1A—H0A 0.889 (14) N1B—H0B 0.879 (14)
O1A—C5A 1.4246 (11) O1B—C6B 1.4244 (11)
O1A—C6A 1.4284 (11) O1B—C5B 1.4248 (11)
C1A—C2A 1.5240 (12) C1B—C2B 1.5284 (12)
C1A—H1A 0.945 (13) C1B—H1B 0.952 (13)
C1A—H2A 0.969 (14) C1B—H2B 0.948 (14)
C2A—C3A 1.5185 (12) C2B—C3B 1.5249 (12)
C2A—H3A 0.959 (14) C2B—H3B 0.941 (14)
C2A—H4A 0.982 (13) C2B—H4B 0.950 (16)
C3A—H5A 0.972 (13) C3B—H5B 0.947 (13)
C3A—H6A 0.956 (14) C3B—H6B 0.967 (13)
C4A—C5A 1.5143 (13) C4B—C5B 1.5171 (12)
C4A—H7A 0.942 (14) C4B—H7B 0.988 (13)
C4A—H8A 0.951 (13) C4B—H8B 0.973 (14)
C5A—H9A 0.984 (14) C5B—H9B 0.953 (13)
C6A—C7A 1.5162 (12) C6B—C7B 1.5182 (12)
C6A—H11A 0.949 (14) C6B—H11B 0.947 (14)
C6A—H12A 0.977 (13) C6B—H12B 0.982 (13)
C7A—H13A 0.944 (14) C7B—H13B 0.919 (13)
C7A—H14A 0.952 (14) C7B—H14B 0.960 (12)
O4A—S1A—O2A 113.99 (4) O2B—S1B—O3B 113.98 (4)
O4A—S1A—O3A 111.82 (4) O2B—S1B—O4B 112.79 (4)
O2A—S1A—O3A 112.05 (4) O3B—S1B—O4B 111.57 (4)
O4A—S1A—C1A 106.02 (4) O2B—S1B—C1B 106.10 (4)
O2A—S1A—C1A 106.77 (4) O3B—S1B—C1B 106.78 (4)
O3A—S1A—C1A 105.49 (4) O4B—S1B—C1B 104.84 (4)
C4A—N1A—C7A 110.70 (6) C3B—N1B—C4B 109.99 (6)
C4A—N1A—C3A 108.38 (7) C3B—N1B—C7B 113.32 (6)
C7A—N1A—C3A 113.23 (7) C4B—N1B—C7B 109.12 (7)
C4A—N1A—H0A 105.8 (9) C3B—N1B—H0B 105.0 (9)
C7A—N1A—H0A 108.9 (9) C4B—N1B—H0B 110.7 (9)
C3A—N1A—H0A 109.5 (9) C7B—N1B—H0B 108.6 (9)
C5A—O1A—C6A 109.30 (7) C6B—O1B—C5B 110.06 (7)
C2A—C1A—S1A 111.34 (6) C2B—C1B—S1B 112.59 (6)
C2A—C1A—H1A 113.6 (8) C2B—C1B—H1B 110.6 (8)
S1A—C1A—H1A 105.3 (8) S1B—C1B—H1B 105.8 (8)
C2A—C1A—H2A 112.5 (8) C2B—C1B—H2B 111.7 (8)
S1A—C1A—H2A 105.6 (9) S1B—C1B—H2B 107.3 (8)
H1A—C1A—H2A 107.9 (12) H1B—C1B—H2B 108.5 (11)
C3A—C2A—C1A 114.64 (7) C3B—C2B—C1B 108.57 (7)
C3A—C2A—H3A 104.3 (8) C3B—C2B—H3B 110.5 (9)
C1A—C2A—H3A 108.8 (8) C1B—C2B—H3B 109.4 (9)
C3A—C2A—H4A 109.3 (8) C3B—C2B—H4B 110.1 (10)
C1A—C2A—H4A 111.0 (8) C1B—C2B—H4B 110.2 (10)
H3A—C2A—H4A 108.4 (11) H3B—C2B—H4B 108.1 (13)
N1A—C3A—C2A 114.03 (7) N1B—C3B—C2B 113.06 (7)
N1A—C3A—H5A 105.6 (8) N1B—C3B—H5B 105.1 (8)
C2A—C3A—H5A 112.0 (8) C2B—C3B—H5B 110.8 (8)
N1A—C3A—H6A 105.9 (8) N1B—C3B—H6B 106.7 (8)
C2A—C3A—H6A 109.2 (8) C2B—C3B—H6B 112.7 (8)
H5A—C3A—H6A 109.8 (11) H5B—C3B—H6B 108.1 (11)
N1A—C4A—C5A 110.96 (7) N1B—C4B—C5B 109.62 (7)
N1A—C4A—H7A 105.6 (8) N1B—C4B—H7B 106.8 (8)
C5A—C4A—H7A 111.4 (8) C5B—C4B—H7B 110.3 (8)
N1A—C4A—H8A 106.1 (8) N1B—C4B—H8B 107.2 (8)
C5A—C4A—H8A 111.2 (8) C5B—C4B—H8B 111.4 (8)
H7A—C4A—H8A 111.3 (11) H7B—C4B—H8B 111.3 (11)
O1A—C5A—C4A 110.53 (7) O1B—C5B—C4B 111.15 (7)
O1A—C5A—H9A 108.2 (8) O1B—C5B—H9B 107.8 (8)
C4A—C5A—H9A 109.4 (8) C4B—C5B—H9B 106.8 (8)
O1A—C5A—H10A 109.9 (8) O1B—C5B—H10B 111.2 (8)
supporting information
sup-7
Acta Cryst. (2005). E61, o3190–o3191H9A—C5A—H10A 109.4 (11) H9B—C5B—H10B 110.0 (11)
O1A—C6A—C7A 111.09 (7) O1B—C6B—C7B 111.60 (7)
O1A—C6A—H11A 108.1 (8) O1B—C6B—H11B 108.2 (8)
C7A—C6A—H11A 108.4 (9) C7B—C6B—H11B 109.3 (8)
O1A—C6A—H12A 109.7 (8) O1B—C6B—H12B 110.3 (8)
C7A—C6A—H12A 110.5 (8) C7B—C6B—H12B 109.3 (8)
H11A—C6A—H12A 108.9 (11) H11B—C6B—H12B 108.1 (11)
N1A—C7A—C6A 110.25 (7) N1B—C7B—C6B 109.06 (7)
N1A—C7A—H13A 107.5 (8) N1B—C7B—H13B 108.1 (8)
C6A—C7A—H13A 110.8 (8) C6B—C7B—H13B 108.2 (8)
N1A—C7A—H14A 107.6 (8) N1B—C7B—H14B 107.6 (8)
C6A—C7A—H14A 111.6 (8) C6B—C7B—H14B 112.5 (8)
H13A—C7A—H14A 109.0 (12) H13B—C7B—H14B 111.2 (11)
N1B—C3B—C2B—C1B −177.97 (7) C3A—C2A—C1A—S1A −173.62 (6)
N1A—C3A—C2A—C1A −60.82 (10) C4A—N1A—C3A—C2A −176.19 (7)
C3B—C2B—C1B—S1B −175.84 (6) C4B—N1B—C3B—C2B 177.91 (7)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N1A—H0A···O4B 0.889 (14) 1.837 (14) 2.7227 (10) 174.4 (14)
N1B—H0B···O3Ai 0.879 (14) 1.915 (14) 2.7871 (10) 171.1 (13)
