2,2,2-Trimethyl-N-(phenyl­sulfon­yl)­acetamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Nirmala, P.G.; Fuess, H.

doi:10.1107/S1600536808019983

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1410

doi:10.1107/S1600536808019983

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2,2,2-Trimethyl-N-(phenylsulfonyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya,^a P. G. Nirmala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 6 June 2008; accepted 30 June 2008; online 5 July 2008)

The N—H and C=O bonds of the SO₂—NH—CO group in the title compound, C₁₁H₁₅NO₃S, are anti to each other. The asymmetric unit contains two independent molecules. The benzene rings form dihedral angles of 83.19 (8) and 76.01 (10)° with the mean planes of the C₂NOS fragments. The molecules are linked into chains parallel to the b axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda, Nayak et al. (2007 ); Gowda, Foro & Fuess (2007 ); Gowda, Kožíšek et al. (2007 ); Gowda, Svoboda et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₅NO₃S
M_r = 241.30
Monoclinic, P 2₁ /c
a = 12.3045 (9) Å
b = 11.3016 (7) Å
c = 18.466 (1) Å
β = 103.117 (6)°
V = 2500.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 299 (2) K
0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.885, T_max = 0.906
15589 measured reflections
4985 independent reflections
3639 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.167
S = 1.16
4985 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4ⁱ	0.86	2.09	2.946 (3)	171
N2—H2N⋯O2ⁱⁱ	0.86	2.32	3.094 (3)	151
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019983/rz2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019983/rz2222Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the substituent effects on the solid state geometries of N-(aryl)-sulfonamides and substituted amides, the structure of N-(phenylsulfonyl)-2,2,2-trimethylacetamide (NPSTMAA) has been determined. The conformations of the N—H and C=O bonds of the SO₂—NH—CO group in NPSTMAA are anti to each other (Fig. 1). The asymmetric unit of the structure contains two molecules. The bond parameters in NPSTMAA are similar to those in N-(aryl)-2,2,2-trimethylacetamides (Gowda, Foro & Fuess, 2007; Gowda, Kožíšek et al., 2007; Gowda, Svoboda et al., 2007) and benzenesulfonamide (Gowda, Nayak et al., 2007). The benzene rings form dihedral angles of 83.19 (8) and 76.01 (10)° with the mean planes of the C₂NOS fragments. A packing diagram of NPSTMAA molecules showing the formation of molecular chains parallel to the b axis through N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For related literature, see: Gowda, Nayak et al. (2007); Gowda, Foro & Fuess (2007); Gowda, Kožíšek et al. (2007); Gowda, Svoboda et al. (2007).

Experimental top

The title compound was prepared by refluxing benzenesulfonamide (0.10 mol) in excess pivalyl chloride (0.20 mol) for about an hour on a water bath. The reaction mixture was cooled and poured into ice-cold water. The resulting solid was separated, washed thoroughly with water and dissolved in a warm sodium hydrogen carbonate solution. The title compound was precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound suitable for X-ray diffraction studies were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The molecular packing of the title compound viewed along tha a axis. Hydrogen bonds are shown as dashed lines.

2,2,2-Trimethyl-N-(phenylsulfonyl)acetamide top

Crystal data top

C₁₁H₁₅NO₃S	F(000) = 1024
M_r = 241.30	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7426 reflections
a = 12.3045 (9) Å	θ = 2.5–28.0°
b = 11.3016 (7) Å	µ = 0.25 mm⁻¹
c = 18.466 (1) Å	T = 299 K
β = 103.117 (6)°	Prism, colourless
V = 2500.9 (3) Å³	0.50 × 0.48 × 0.40 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4985 independent reflections
Radiation source: fine-focus sealed tube	3639 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −15→15
T_min = 0.885, T_max = 0.906	k = −13→13
15589 measured reflections	l = −21→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0676P)² + 1.8991P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.002
4985 reflections	Δρ_max = 0.44 e Å⁻³
290 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.100 (4)

Crystal data top

C₁₁H₁₅NO₃S	V = 2500.9 (3) Å³
M_r = 241.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3045 (9) Å	µ = 0.25 mm⁻¹
b = 11.3016 (7) Å	T = 299 K
c = 18.466 (1) Å	0.50 × 0.48 × 0.40 mm
β = 103.117 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4985 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3639 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.906	R_int = 0.029
15589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.16	Δρ_max = 0.44 e Å⁻³
4985 reflections	Δρ_min = −0.40 e Å⁻³
290 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
C1	0.6562 (2)	0.7079 (2)	0.00179 (14)	0.0448 (6)
C2	0.7702 (3)	0.7222 (3)	0.00846 (18)	0.0580 (8)
H2	0.8043	0.7948	0.0223	0.070*
C3	0.8318 (3)	0.6267 (3)	−0.0058 (2)	0.0693 (9)
H3	0.9082	0.6350	−0.0015	0.083*
C4	0.7817 (3)	0.5195 (3)	−0.02624 (19)	0.0679 (9)
H4	0.8244	0.4554	−0.0350	0.081*
C5	0.6688 (3)	0.5067 (3)	−0.03380 (18)	0.0624 (8)
H5	0.6350	0.4344	−0.0486	0.075*
C6	0.6053 (3)	0.6003 (3)	−0.01956 (16)	0.0515 (7)
H6	0.5289	0.5913	−0.0242	0.062*
C7	0.5886 (2)	0.7797 (2)	0.15920 (15)	0.0440 (6)
C8	0.6204 (3)	0.8245 (3)	0.23927 (15)	0.0541 (7)
C9	0.5795 (4)	0.7357 (4)	0.2886 (2)	0.0894 (13)
H9A	0.6138	0.6603	0.2849	0.107*
H9B	0.5000	0.7281	0.2730	0.107*
H9C	0.5990	0.7625	0.3393	0.107*
C10	0.5687 (3)	0.9456 (3)	0.24601 (19)	0.0713 (9)
H10A	0.4889	0.9399	0.2307	0.086*
H10B	0.5953	1.0013	0.2148	0.086*
H10C	0.5892	0.9718	0.2967	0.086*
C11	0.7482 (3)	0.8339 (4)	0.2623 (2)	0.0856 (12)
H11A	0.7740	0.8874	0.2295	0.103*
H11B	0.7805	0.7572	0.2596	0.103*
H11C	0.7698	0.8630	0.3124	0.103*
N1	0.6084 (2)	0.8572 (2)	0.10554 (12)	0.0499 (6)
H1N	0.6401	0.9236	0.1200	0.060*
O1	0.46068 (17)	0.79593 (19)	−0.00518 (12)	0.0590 (6)
O2	0.6126 (2)	0.93176 (18)	−0.01691 (11)	0.0613 (6)
O3	0.54943 (18)	0.68328 (17)	0.14170 (11)	0.0541 (5)
S1	0.57470 (6)	0.82976 (6)	0.01579 (4)	0.0467 (2)
C12	0.8299 (2)	0.2840 (2)	0.14176 (14)	0.0476 (6)
C13	0.9320 (3)	0.3399 (3)	0.15839 (18)	0.0678 (9)
H13	0.9972	0.2991	0.1572	0.081*
C14	0.9346 (6)	0.4580 (5)	0.1769 (2)	0.1085 (19)
H14	1.0028	0.4973	0.1888	0.130*
C15	0.8403 (8)	0.5176 (4)	0.1781 (3)	0.120 (2)
H15	0.8442	0.5975	0.1905	0.144*
C16	0.7397 (5)	0.4626 (4)	0.1615 (2)	0.0985 (16)
H16	0.6752	0.5051	0.1625	0.118*
C17	0.7324 (3)	0.3431 (3)	0.14311 (17)	0.0657 (9)
H17	0.6640	0.3042	0.1321	0.079*
C18	0.8663 (2)	0.1631 (3)	−0.01406 (16)	0.0531 (7)
C19	0.8292 (3)	0.1401 (3)	−0.09727 (16)	0.0547 (7)
C20	0.9144 (4)	0.1923 (4)	−0.1351 (2)	0.0894 (13)
H20A	0.9856	0.1557	−0.1160	0.107*
H20B	0.9202	0.2759	−0.1258	0.107*
H20C	0.8918	0.1785	−0.1877	0.107*
C21	0.8234 (4)	0.0072 (4)	−0.1109 (2)	0.0822 (11)
H21A	0.7707	−0.0273	−0.0859	0.099*
H21B	0.8957	−0.0271	−0.0921	0.099*
H21C	0.8002	−0.0079	−0.1633	0.099*
C22	0.7149 (4)	0.1925 (5)	−0.1277 (2)	0.0991 (15)
H22A	0.7175	0.2764	−0.1193	0.119*
H22B	0.6622	0.1573	−0.1030	0.119*
H22C	0.6925	0.1771	−0.1801	0.119*
N2	0.7948 (2)	0.1235 (2)	0.02886 (12)	0.0541 (6)
H2N	0.7323	0.0925	0.0067	0.065*
O4	0.7261 (2)	0.0845 (2)	0.13953 (12)	0.0719 (7)
O5	0.9285 (2)	0.0813 (2)	0.15009 (14)	0.0811 (8)
O6	0.9519 (2)	0.2109 (3)	0.01479 (13)	0.0823 (8)
S2	0.82357 (6)	0.13285 (7)	0.12026 (4)	0.0512 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0553 (15)	0.0441 (14)	0.0354 (12)	−0.0074 (12)	0.0111 (11)	−0.0005 (10)
C2	0.0561 (17)	0.0525 (17)	0.0625 (18)	−0.0116 (14)	0.0070 (14)	0.0000 (14)
C3	0.0572 (19)	0.076 (2)	0.077 (2)	0.0004 (17)	0.0198 (16)	0.0044 (18)
C4	0.081 (2)	0.061 (2)	0.068 (2)	0.0118 (17)	0.0315 (17)	−0.0010 (16)
C5	0.082 (2)	0.0481 (17)	0.0640 (19)	−0.0070 (15)	0.0306 (16)	−0.0093 (14)
C6	0.0598 (17)	0.0494 (16)	0.0481 (15)	−0.0122 (13)	0.0184 (12)	−0.0038 (12)
C7	0.0478 (14)	0.0402 (14)	0.0453 (14)	0.0023 (11)	0.0132 (11)	−0.0035 (11)
C8	0.0719 (19)	0.0524 (16)	0.0370 (14)	−0.0026 (14)	0.0103 (13)	−0.0038 (12)
C9	0.144 (4)	0.079 (3)	0.0471 (18)	−0.019 (3)	0.027 (2)	0.0023 (17)
C10	0.092 (3)	0.067 (2)	0.0593 (19)	0.0040 (19)	0.0272 (18)	−0.0160 (16)
C11	0.082 (3)	0.099 (3)	0.064 (2)	0.008 (2)	−0.0068 (19)	−0.011 (2)
N1	0.0684 (15)	0.0436 (12)	0.0376 (11)	−0.0118 (11)	0.0119 (10)	−0.0049 (9)
O1	0.0524 (12)	0.0616 (13)	0.0582 (12)	0.0000 (10)	0.0025 (9)	−0.0063 (10)
O2	0.0892 (16)	0.0466 (11)	0.0499 (11)	−0.0053 (11)	0.0195 (10)	0.0045 (9)
O3	0.0697 (13)	0.0420 (11)	0.0520 (11)	−0.0059 (9)	0.0165 (9)	−0.0025 (8)
S1	0.0585 (4)	0.0419 (4)	0.0387 (4)	−0.0035 (3)	0.0088 (3)	−0.0003 (3)
C12	0.0596 (17)	0.0470 (15)	0.0345 (13)	−0.0036 (12)	0.0071 (11)	−0.0018 (11)
C13	0.077 (2)	0.075 (2)	0.0491 (17)	−0.0233 (18)	0.0108 (15)	−0.0077 (15)
C14	0.172 (5)	0.084 (3)	0.068 (3)	−0.066 (4)	0.023 (3)	−0.021 (2)
C15	0.244 (8)	0.054 (3)	0.064 (3)	−0.014 (4)	0.039 (4)	−0.011 (2)
C16	0.164 (5)	0.078 (3)	0.057 (2)	0.056 (3)	0.031 (3)	0.005 (2)
C17	0.077 (2)	0.072 (2)	0.0467 (16)	0.0168 (17)	0.0098 (15)	0.0002 (15)
C18	0.0506 (16)	0.0640 (18)	0.0474 (16)	−0.0065 (14)	0.0164 (12)	−0.0095 (13)
C19	0.0563 (17)	0.0657 (19)	0.0445 (15)	−0.0009 (14)	0.0164 (12)	−0.0089 (13)
C20	0.111 (3)	0.112 (3)	0.053 (2)	−0.033 (3)	0.036 (2)	−0.012 (2)
C21	0.114 (3)	0.074 (2)	0.068 (2)	−0.010 (2)	0.040 (2)	−0.0204 (18)
C22	0.085 (3)	0.152 (4)	0.056 (2)	0.037 (3)	0.0070 (19)	−0.008 (2)
N2	0.0570 (14)	0.0692 (16)	0.0382 (12)	−0.0159 (12)	0.0152 (10)	−0.0152 (11)
O4	0.0986 (18)	0.0684 (15)	0.0565 (13)	−0.0316 (13)	0.0338 (12)	−0.0093 (11)
O5	0.0916 (18)	0.0805 (17)	0.0672 (15)	0.0328 (14)	0.0099 (13)	0.0079 (13)
O6	0.0625 (14)	0.132 (2)	0.0541 (13)	−0.0361 (15)	0.0165 (11)	−0.0164 (14)
S2	0.0652 (5)	0.0477 (4)	0.0410 (4)	−0.0019 (3)	0.0130 (3)	−0.0016 (3)

Geometric parameters (Å, º) top

C1—C6	1.384 (4)	C12—C13	1.377 (4)
C1—C2	1.389 (4)	C12—C17	1.378 (4)
C1—S1	1.757 (3)	C12—S2	1.752 (3)
C2—C3	1.378 (5)	C13—C14	1.376 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.373 (5)	C14—C15	1.347 (8)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.372 (5)	C15—C16	1.357 (8)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.375 (4)	C16—C17	1.391 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—O3	1.206 (3)	C18—O6	1.195 (4)
C7—N1	1.384 (3)	C18—N2	1.386 (4)
C7—C8	1.527 (4)	C18—C19	1.523 (4)
C8—C9	1.516 (5)	C19—C20	1.506 (5)
C8—C10	1.526 (5)	C19—C22	1.512 (5)
C8—C11	1.536 (5)	C19—C21	1.522 (5)
C9—H9A	0.9600	C20—H20A	0.9600
C9—H9B	0.9600	C20—H20B	0.9600
C9—H9C	0.9600	C20—H20C	0.9600
C10—H10A	0.9600	C21—H21A	0.9600
C10—H10B	0.9600	C21—H21B	0.9600
C10—H10C	0.9600	C21—H21C	0.9600
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
N1—S1	1.644 (2)	N2—S2	1.647 (2)
N1—H1N	0.8600	N2—H2N	0.8600
O1—S1	1.421 (2)	O4—S2	1.434 (2)
O2—S1	1.428 (2)	O5—S2	1.410 (2)

C6—C1—C2	120.7 (3)	C13—C12—C17	121.9 (3)
C6—C1—S1	119.6 (2)	C13—C12—S2	119.3 (3)
C2—C1—S1	119.6 (2)	C17—C12—S2	118.8 (2)
C3—C2—C1	118.7 (3)	C14—C13—C12	118.0 (4)
C3—C2—H2	120.7	C14—C13—H13	121.0
C1—C2—H2	120.7	C12—C13—H13	121.0
C4—C3—C2	120.8 (3)	C15—C14—C13	121.2 (5)
C4—C3—H3	119.6	C15—C14—H14	119.4
C2—C3—H3	119.6	C13—C14—H14	119.4
C5—C4—C3	120.1 (3)	C14—C15—C16	120.9 (4)
C5—C4—H4	119.9	C14—C15—H15	119.6
C3—C4—H4	119.9	C16—C15—H15	119.6
C4—C5—C6	120.4 (3)	C15—C16—C17	120.3 (5)
C4—C5—H5	119.8	C15—C16—H16	119.9
C6—C5—H5	119.8	C17—C16—H16	119.9
C5—C6—C1	119.4 (3)	C12—C17—C16	117.8 (4)
C5—C6—H6	120.3	C12—C17—H17	121.1
C1—C6—H6	120.3	C16—C17—H17	121.1
O3—C7—N1	120.3 (2)	O6—C18—N2	120.0 (3)
O3—C7—C8	123.9 (3)	O6—C18—C19	124.0 (3)
N1—C7—C8	115.8 (2)	N2—C18—C19	116.0 (2)
C9—C8—C10	110.1 (3)	C20—C19—C22	111.2 (4)
C9—C8—C7	108.4 (3)	C20—C19—C21	108.7 (3)
C10—C8—C7	110.9 (2)	C22—C19—C21	108.7 (3)
C9—C8—C11	109.7 (3)	C20—C19—C18	108.7 (3)
C10—C8—C11	109.6 (3)	C22—C19—C18	110.4 (3)
C7—C8—C11	108.2 (3)	C21—C19—C18	109.1 (3)
C8—C9—H9A	109.5	C19—C20—H20A	109.5
C8—C9—H9B	109.5	C19—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C8—C9—H9C	109.5	C19—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
C8—C10—H10A	109.5	C19—C21—H21A	109.5
C8—C10—H10B	109.5	C19—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
C8—C10—H10C	109.5	C19—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
C8—C11—H11A	109.5	C19—C22—H22A	109.5
C8—C11—H11B	109.5	C19—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C8—C11—H11C	109.5	C19—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C7—N1—S1	123.86 (19)	C18—N2—S2	123.3 (2)
C7—N1—H1N	118.1	C18—N2—H2N	118.4
S1—N1—H1N	118.1	S2—N2—H2N	118.4
O1—S1—O2	119.96 (14)	O5—S2—O4	119.27 (17)
O1—S1—N1	109.45 (13)	O5—S2—N2	109.80 (14)
O2—S1—N1	104.02 (12)	O4—S2—N2	103.43 (13)
O1—S1—C1	108.08 (13)	O5—S2—C12	108.93 (16)
O2—S1—C1	108.55 (13)	O4—S2—C12	108.21 (14)
N1—S1—C1	105.93 (12)	N2—S2—C12	106.43 (13)

C6—C1—C2—C3	−0.7 (4)	C17—C12—C13—C14	0.2 (5)
S1—C1—C2—C3	−177.3 (3)	S2—C12—C13—C14	−178.4 (3)
C1—C2—C3—C4	0.1 (5)	C12—C13—C14—C15	−0.6 (6)
C2—C3—C4—C5	0.9 (5)	C13—C14—C15—C16	0.4 (7)
C3—C4—C5—C6	−1.3 (5)	C14—C15—C16—C17	0.2 (7)
C4—C5—C6—C1	0.6 (5)	C13—C12—C17—C16	0.4 (5)
C2—C1—C6—C5	0.4 (4)	S2—C12—C17—C16	179.0 (3)
S1—C1—C6—C5	177.0 (2)	C15—C16—C17—C12	−0.6 (6)
O3—C7—C8—C9	−7.8 (4)	O6—C18—C19—C20	−2.7 (5)
N1—C7—C8—C9	172.8 (3)	N2—C18—C19—C20	178.1 (3)
O3—C7—C8—C10	−128.7 (3)	O6—C18—C19—C22	−124.9 (4)
N1—C7—C8—C10	51.9 (4)	N2—C18—C19—C22	56.0 (4)
O3—C7—C8—C11	111.1 (3)	O6—C18—C19—C21	115.7 (4)
N1—C7—C8—C11	−68.3 (3)	N2—C18—C19—C21	−63.4 (4)
O3—C7—N1—S1	3.8 (4)	O6—C18—N2—S2	−2.9 (5)
C8—C7—N1—S1	−176.8 (2)	C19—C18—N2—S2	176.2 (2)
C7—N1—S1—O1	51.8 (3)	C18—N2—S2—O5	−53.0 (3)
C7—N1—S1—O2	−178.8 (2)	C18—N2—S2—O4	178.7 (3)
C7—N1—S1—C1	−64.5 (3)	C18—N2—S2—C12	64.7 (3)
C6—C1—S1—O1	−5.4 (3)	C13—C12—S2—O5	22.0 (3)
C2—C1—S1—O1	171.3 (2)	C17—C12—S2—O5	−156.6 (2)
C6—C1—S1—O2	−136.9 (2)	C13—C12—S2—O4	153.0 (2)
C2—C1—S1—O2	39.7 (3)	C17—C12—S2—O4	−25.5 (3)
C6—C1—S1—N1	111.9 (2)	C13—C12—S2—N2	−96.4 (2)
C2—C1—S1—N1	−71.5 (3)	C17—C12—S2—N2	85.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ⁱ	0.86	2.09	2.946 (3)	171
N2—H2N···O2ⁱⁱ	0.86	2.32	3.094 (3)	151

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅NO₃S
M_r	241.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	12.3045 (9), 11.3016 (7), 18.466 (1)
β (°)	103.117 (6)
V (Å³)	2500.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.50 × 0.48 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.885, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	15589, 4985, 3639
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.167, 1.16
No. of reflections	4985
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.40

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ⁱ	0.86	2.09	2.946 (3)	170.9
N2—H2N···O2ⁱⁱ	0.86	2.32	3.094 (3)	150.6

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2329–o2330. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Gowda, B. T., Nayak, R., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007). Acta Cryst. E63, o2967. Web of Science CSD CrossRef IUCr Journals Google Scholar
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