3-(Morpholinium-1-yl)propane­sulfonate

Chruszcz, M.; Zheng, H.; Cymborowski, M.; Gawlicka-Chruszcz, A.; Minor, W.

doi:10.1107/S1600536805027728

3-(Morpholinium-1-yl)propanesulfonate

M. Chruszcz, H. Zheng, M. Cymborowski, A. Gawlicka-Chruszcz and W. Minor

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027728/kp6056sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027728/kp6056Isup2.hkl Contains datablock I

CCDC reference: 287618

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Key indicators

Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.001 Å
R factor = 0.026
wR factor = 0.075
Data-to-parameter ratio = 18.5

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No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H15 N O4 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

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.

Experimental top

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 1 M MOPS solution in Solvent?.

Computing details top

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) and HKL-2000; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and HKL-2000; molecular graphics: HKL-2000, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and O (Jones et al., 1991); software used to prepare material for publication: HKL-2000 and SHELXL97.

Figures top

Fig. 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 top

Crystal data top

C₇H₁₅NO₄S	F(000) = 896
M_r = 209.26	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71074 Å
Hall symbol: -P 2ybc	Cell parameters from 12720 reflections
a = 6.149 (1) Å	θ = 2.3–32.0°
b = 11.255 (1) Å	µ = 0.33 mm⁻¹
c = 27.402 (1) Å	T = 103 K
β = 90.431 (1)°	Plate, colourless
V = 1896.4 (4) Å³	0.10 × 0.10 × 0.02 mm
Z = 8

Data collection top

Goniostat vertical Euler diffractometer	6578 independent reflections
Radiation source: fine-focus sealed tube	5857 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
Detector resolution: 10.0 pixels mm^-1	θ_max = 32.0°, θ_min = 2.3°
ω scan with χ offset	h = −9→9
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −16→16
T_min = 0.958, T_max = 0.994	l = −40→40
12720 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: difference Fourier map
wR(F²) = 0.075	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0397P)² + 0.5917P] where P = (F_o² + 2F_c²)/3
6578 reflections	(Δ/σ)_max = 0.001
355 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₇H₁₅NO₄S	V = 1896.4 (4) Å³
M_r = 209.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.149 (1) Å	µ = 0.33 mm⁻¹
b = 11.255 (1) Å	T = 103 K
c = 27.402 (1) Å	0.10 × 0.10 × 0.02 mm
β = 90.431 (1)°

Data collection top

Goniostat vertical Euler diffractometer	6578 independent reflections
Absorption correction: multi-scan (Otwinowski et al., 2003)	5857 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.994	R_int = 0.012
12720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.075	All H-atom parameters refined
S = 1.06	Δρ_max = 0.45 e Å⁻³
6578 reflections	Δρ_min = −0.41 e Å⁻³
355 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)*
H6A	0.337 (2)	0.3547 (12)	0.2347 (5)	0.022 (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) top

	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)
O2A	0.0202 (3)	0.0138 (3)	0.0154 (3)	−0.0006 (2)	−0.0025 (2)	0.0024 (2)
O3A	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) top

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)
C5A—H10A	0.974 (14)	C5B—H10B	0.980 (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)
C4A—C5A—H10A	109.4 (8)	C4B—C5B—H10B	109.7 (8)
H9A—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) top

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)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₇H₁₅NO₄S
M_r	209.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	103
a, b, c (Å)	6.149 (1), 11.255 (1), 27.402 (1)
β (°)	90.431 (1)
V (Å³)	1896.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.10 × 0.10 × 0.02

Data collection
Diffractometer	Goniostat vertical Euler diffractometer
Absorption correction	Multi-scan (Otwinowski et al., 2003)
T_min, T_max	0.958, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	12720, 6578, 5857
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.075, 1.06
No. of reflections	6578
No. of parameters	355
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.41

Computer programs: HKL-2000 (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990) and HKL-2000, SHELXL97 (Sheldrick, 1997) and HKL-2000, HKL-2000, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and O (Jones et al., 1991), HKL-2000 and SHELXL97.

Selected torsion angles (º) top

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)