2,2-Dimethyl-N-(2-methyl­phenyl­sulfon­yl)acetamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811027838

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2055

doi:10.1107/S1600536811027838

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2,2-Dimethyl-N-(2-methylphenylsulfonyl)acetamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 3 July 2011; accepted 11 July 2011; online 16 July 2011)

The asymmetric unit of the title compound, C₁₁H₁₅NO₃S, contains two independent molecules in which the amide bonds show a trans conformation. The C—S—N—C torsion angles are −67.4 (2) and 63.8 (2)° in the two independent molecules. In one of the molecules, a methyl group is disordered over two sets of sites with a site-occupation factor of 0.661 (16) for the major occupany component. In the crystal, molecules are packed into chains running along [101] through N—H⋯O(S) hydrogen bonds.

Related literature

For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ); Gowda et al. (2007 ), on N-(aryl)-sulfonamides, see: Gowda et al. (2005 ), and on N-(arylsulfonyl)-amides, see: Shakuntala et al. (2011a ,b )

Experimental

Crystal data

C₁₁H₁₅NO₃S
M_r = 241.30
Monoclinic, P 2₁ /n
a = 11.829 (1) Å
b = 16.351 (1) Å
c = 13.351 (1) Å
β = 96.485 (8)°
V = 2565.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.46 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.896, T_max = 0.908
9793 measured reflections
5225 independent reflections
3538 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.06
5225 reflections
306 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6	0.82 (2)	2.02 (2)	2.844 (2)	175 (2)
N2—H2N⋯O3ⁱ	0.81 (2)	2.08 (2)	2.870 (2)	167 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027838/bt5569sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027838/bt5569Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027838/bt5569Isup3.cml

checkCIF report

Comment top

The hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2007), N-(aryl)-sulfonamides (Gowda et al., 2005) and N-(arylsulfonyl)-amides (Shakuntala et al., 2011a,b). As a part of studying the effects of substituents on the structures of this class of compounds, the structure of N-(2-methylphenylsulfonyl)-2,2-dimethylacetamide (I) has been determined (Fig. 1). In (I), the asymmetric unit contains two independent molecules. The conformations of the N—H and C=O bonds in the side chains are anti to each other, similar to that observed in N-(2-methylphenylsulfonyl)-acetamide (II) (Shakuntala et al., 2011b) and N-(2-chlorophenylsulfonyl)-2,2-dimethylacetamide (III) (Shakuntala et al., 2011a).

Further, in both the independent molecules, the conformation of the amide H atoms are syn to the ortho-methyl groups in the benzene rings, similar to that observed between the amide H atom and the ortho-methyl group in (II), but contrary to the anti conformation observed between the amide H atom and the ortho-chloro group in (III).

The molecules in (I) are bent at the S-atoms with a C—S—N—C torsion angle of -67.4 (2)° and 63.8 (2)° in the two independent molecules, compared to the values of -58.2 (2)° in (II) and 64.4 (2)° in (III). Further, the dihedral angle between the benzene rings and the SO2—NH—CO—C groups in (I) are 86.1 (2)° (molecule 1) and 87.4 (2)° (molecule 2), compared to the values of 87.0 (1)° in (II) and 87.4 (1)° in (III).

In the crystal structure, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into chains. Part of the crystal structure is shown in Fig. 2.

Related literature top

For hydrogen bonding modes of sulfonamides, see; Adsmond & Grant (2001). For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2007), on N-(aryl)-sulfonamides, see: Gowda et al. (2005), and on N-(arylsulfonyl)-amides, see: Shakuntala et al. (2011a,b)

Experimental top

The title compound was prepared by refluxing 2-methylbenzenesulfonamide (0.10 mole) with an excess of 2,2-dimethylacetyl chloride (0.20 mole) for one 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 warm dilute sodium hydrogen carbonate solution. The title compound was reprecipitated 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 further characterized by recording its infrared spectra.

Prism like colorless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of an ethanolic solution of the compound.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom- labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

2,2-Dimethyl-N-(2-methylphenylsulfonyl)acetamide top

Crystal data top

C₁₁H₁₅NO₃S	F(000) = 1024
M_r = 241.30	D_x = 1.249 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2934 reflections
a = 11.829 (1) Å	θ = 2.9–27.7°
b = 16.351 (1) Å	µ = 0.25 mm⁻¹
c = 13.351 (1) Å	T = 293 K
β = 96.485 (8)°	Prism, colourless
V = 2565.8 (3) Å³	0.46 × 0.44 × 0.40 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5225 independent reflections
Radiation source: fine-focus sealed tube	3538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
T_min = 0.896, T_max = 0.908	k = −20→15
9793 measured reflections	l = −16→14

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0663P)² + 0.310P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5225 reflections	Δρ_max = 0.25 e Å⁻³
306 parameters	Δρ_min = −0.32 e Å⁻³
5 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: 0.0160 (11)

Crystal data top

C₁₁H₁₅NO₃S	V = 2565.8 (3) Å³
M_r = 241.30	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.829 (1) Å	µ = 0.25 mm⁻¹
b = 16.351 (1) Å	T = 293 K
c = 13.351 (1) Å	0.46 × 0.44 × 0.40 mm
β = 96.485 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5225 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3538 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.908	R_int = 0.015
9793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	5 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
5225 reflections	Δρ_min = −0.32 e Å⁻³
306 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	Occ. (<1)
C1	0.24942 (16)	0.90807 (11)	0.25752 (15)	0.0439 (5)
C2	0.24885 (19)	0.97836 (13)	0.31734 (18)	0.0566 (6)
C3	0.2774 (2)	1.05064 (15)	0.2737 (2)	0.0771 (8)
H3	0.2784	1.0986	0.3112	0.093*
C4	0.3040 (3)	1.05412 (18)	0.1779 (3)	0.0960 (10)
H4	0.3225	1.1042	0.1512	0.115*
C5	0.3042 (3)	0.98543 (19)	0.1197 (2)	0.0959 (10)
H5	0.3230	0.9886	0.0540	0.115*
C6	0.2762 (2)	0.91095 (15)	0.16000 (18)	0.0641 (6)
H6	0.2755	0.8635	0.1215	0.077*
C7	0.3989 (2)	0.77526 (15)	0.41066 (16)	0.0557 (6)
C8	0.4565 (3)	0.7573 (2)	0.5134 (2)	0.0990 (10)
H8A	0.4036	0.7839	0.5547	0.119*	0.661 (16)
H8B	0.4179	0.7894	0.5617	0.119*	0.339 (16)
C9	0.4490 (4)	0.6760 (2)	0.5464 (3)	0.1276 (15)
H9A	0.4842	0.6403	0.5018	0.153*
H9B	0.3705	0.6611	0.5464	0.153*
H9C	0.4873	0.6709	0.6134	0.153*
C10A	0.5512 (10)	0.8134 (5)	0.5426 (7)	0.121 (4)	0.661 (16)
H10A	0.5244	0.8688	0.5369	0.145*	0.661 (16)
H10B	0.6094	0.8054	0.4989	0.145*	0.661 (16)
H10C	0.5818	0.8026	0.6110	0.145*	0.661 (16)
C10B	0.4852 (11)	0.8264 (5)	0.5782 (8)	0.072 (3)	0.339 (16)
H10D	0.5199	0.8075	0.6425	0.086*	0.339 (16)
H10E	0.4174	0.8566	0.5871	0.086*	0.339 (16)
H10F	0.5375	0.8612	0.5482	0.086*	0.339 (16)
C11	0.2176 (3)	0.97897 (18)	0.4234 (2)	0.0941 (10)
H11A	0.2694	0.9447	0.4651	0.113*
H11B	0.1415	0.9587	0.4238	0.113*
H11C	0.2220	1.0339	0.4491	0.113*
N1	0.28574 (16)	0.79150 (11)	0.40442 (13)	0.0498 (4)
H1N	0.2555 (19)	0.7959 (15)	0.4568 (14)	0.060*
O1	0.09374 (14)	0.82144 (12)	0.32966 (16)	0.0884 (6)
O2	0.22413 (17)	0.75295 (9)	0.22545 (13)	0.0776 (5)
O3	0.44952 (15)	0.77645 (13)	0.33654 (13)	0.0803 (6)
S1	0.20407 (5)	0.81269 (3)	0.29885 (4)	0.05239 (18)
C12	0.25372 (19)	0.94032 (13)	0.75834 (16)	0.0540 (5)
C13	0.1651 (2)	0.99676 (15)	0.7539 (2)	0.0689 (7)
C14	0.1867 (3)	1.07325 (18)	0.7135 (2)	0.0941 (10)
H14	0.1293	1.1124	0.7074	0.113*
C15	0.2888 (4)	1.0921 (2)	0.6828 (3)	0.1094 (12)
H15	0.2998	1.1437	0.6563	0.131*
C16	0.3756 (3)	1.0370 (2)	0.6901 (3)	0.1032 (11)
H16	0.4458	1.0510	0.6700	0.124*
C17	0.3575 (2)	0.96009 (17)	0.7278 (2)	0.0770 (8)
H17	0.4157	0.9215	0.7326	0.092*
C18	0.12222 (18)	0.78145 (13)	0.64273 (16)	0.0475 (5)
C19	0.0175 (2)	0.73490 (15)	0.60130 (17)	0.0587 (6)
H19	−0.0153	0.7092	0.6577	0.070*
C20	−0.0680 (2)	0.7950 (2)	0.5511 (3)	0.0923 (9)
H20A	−0.0360	0.8223	0.4972	0.111*
H20B	−0.0867	0.8346	0.5997	0.111*
H20C	−0.1356	0.7663	0.5246	0.111*
C21	0.0469 (3)	0.66856 (17)	0.5299 (2)	0.0847 (9)
H21A	0.1004	0.6314	0.5650	0.102*
H21B	0.0799	0.6927	0.4745	0.102*
H21C	−0.0209	0.6394	0.5049	0.102*
C22	0.0524 (2)	0.9796 (2)	0.7900 (3)	0.1058 (11)
H22A	0.0632	0.9669	0.8606	0.127*
H22B	0.0172	0.9341	0.7534	0.127*
H22C	0.0045	1.0269	0.7791	0.127*
N2	0.13051 (15)	0.79850 (11)	0.74326 (13)	0.0484 (4)
H2N	0.0846 (17)	0.7801 (14)	0.7778 (16)	0.058*
O4	0.34155 (14)	0.79679 (11)	0.79255 (15)	0.0763 (5)
O5	0.21005 (16)	0.84663 (12)	0.90834 (12)	0.0793 (5)
O6	0.19510 (14)	0.80550 (11)	0.59210 (12)	0.0650 (5)
S2	0.24242 (5)	0.84139 (4)	0.80908 (4)	0.05448 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0460 (11)	0.0338 (10)	0.0508 (12)	0.0038 (9)	0.0004 (9)	0.0021 (8)
C2	0.0646 (14)	0.0393 (12)	0.0641 (14)	0.0062 (10)	−0.0001 (11)	−0.0043 (10)
C3	0.099 (2)	0.0351 (13)	0.097 (2)	−0.0028 (13)	0.0053 (16)	−0.0023 (13)
C4	0.123 (3)	0.0485 (17)	0.121 (3)	−0.0030 (17)	0.034 (2)	0.0257 (17)
C5	0.136 (3)	0.075 (2)	0.085 (2)	0.0200 (19)	0.050 (2)	0.0288 (17)
C6	0.0875 (18)	0.0487 (14)	0.0581 (14)	0.0144 (12)	0.0162 (12)	0.0046 (11)
C7	0.0590 (14)	0.0630 (15)	0.0451 (12)	0.0084 (11)	0.0056 (10)	0.0098 (10)
C8	0.108 (2)	0.123 (3)	0.0601 (18)	−0.004 (2)	−0.0171 (16)	0.0297 (18)
C9	0.168 (4)	0.113 (3)	0.092 (2)	−0.006 (3)	−0.028 (2)	0.054 (2)
C10A	0.142 (8)	0.126 (5)	0.081 (4)	−0.010 (5)	−0.043 (5)	0.018 (4)
C10B	0.058 (6)	0.089 (7)	0.066 (6)	−0.001 (5)	0.000 (4)	−0.005 (4)
C11	0.150 (3)	0.0631 (18)	0.0695 (18)	0.0237 (18)	0.0144 (18)	−0.0181 (13)
N1	0.0553 (11)	0.0534 (11)	0.0426 (10)	0.0039 (8)	0.0140 (8)	0.0064 (8)
O1	0.0473 (10)	0.0915 (15)	0.1265 (17)	−0.0073 (9)	0.0104 (10)	0.0322 (12)
O2	0.1242 (15)	0.0351 (8)	0.0670 (11)	−0.0057 (9)	−0.0176 (10)	−0.0091 (7)
O3	0.0660 (11)	0.1159 (16)	0.0623 (11)	0.0321 (10)	0.0218 (9)	0.0169 (10)
S1	0.0526 (3)	0.0400 (3)	0.0622 (4)	−0.0057 (2)	−0.0041 (2)	0.0048 (2)
C12	0.0569 (13)	0.0462 (12)	0.0566 (13)	−0.0050 (10)	−0.0041 (10)	−0.0071 (10)
C13	0.0740 (17)	0.0484 (14)	0.0807 (18)	0.0047 (12)	−0.0070 (13)	−0.0155 (12)
C14	0.126 (3)	0.0484 (17)	0.101 (2)	0.0135 (18)	−0.016 (2)	−0.0136 (15)
C15	0.165 (4)	0.0490 (18)	0.113 (3)	−0.026 (2)	0.009 (3)	−0.0052 (17)
C16	0.112 (3)	0.077 (2)	0.123 (3)	−0.042 (2)	0.022 (2)	−0.0035 (19)
C17	0.0714 (17)	0.0647 (17)	0.095 (2)	−0.0182 (14)	0.0082 (14)	−0.0027 (14)
C18	0.0501 (12)	0.0457 (12)	0.0485 (12)	−0.0006 (9)	0.0134 (10)	−0.0045 (9)
C19	0.0616 (14)	0.0678 (16)	0.0490 (13)	−0.0193 (12)	0.0164 (11)	−0.0106 (11)
C20	0.0634 (17)	0.106 (2)	0.104 (2)	−0.0036 (17)	−0.0055 (15)	−0.0181 (19)
C21	0.102 (2)	0.0694 (19)	0.084 (2)	−0.0232 (16)	0.0195 (16)	−0.0267 (14)
C22	0.075 (2)	0.087 (2)	0.154 (3)	0.0248 (17)	0.009 (2)	−0.029 (2)
N2	0.0493 (11)	0.0518 (11)	0.0455 (10)	−0.0092 (8)	0.0117 (8)	−0.0011 (8)
O4	0.0547 (10)	0.0647 (11)	0.1057 (14)	0.0137 (8)	−0.0069 (9)	0.0100 (10)
O5	0.0944 (14)	0.0959 (14)	0.0447 (9)	−0.0164 (11)	−0.0041 (8)	0.0007 (9)
O6	0.0611 (10)	0.0820 (12)	0.0556 (9)	−0.0186 (9)	0.0232 (8)	−0.0101 (8)
S2	0.0530 (3)	0.0532 (3)	0.0549 (3)	−0.0023 (3)	−0.0044 (2)	0.0031 (2)

Geometric parameters (Å, º) top

C1—C6	1.375 (3)	N1—H1N	0.824 (16)
C1—C2	1.400 (3)	O1—S1	1.4193 (18)
C1—S1	1.758 (2)	O2—S1	1.4224 (17)
C2—C3	1.377 (3)	C12—C17	1.375 (3)
C2—C11	1.504 (3)	C12—C13	1.393 (3)
C3—C4	1.352 (4)	C12—S2	1.765 (2)
C3—H3	0.9300	C13—C14	1.397 (4)
C4—C5	1.366 (4)	C13—C22	1.493 (4)
C4—H4	0.9300	C14—C15	1.354 (5)
C5—C6	1.387 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.361 (5)
C6—H6	0.9300	C15—H15	0.9300
C7—O3	1.214 (2)	C16—C17	1.381 (4)
C7—N1	1.357 (3)	C16—H16	0.9300
C7—C8	1.491 (3)	C17—H17	0.9300
C8—C9	1.407 (5)	C18—O6	1.219 (2)
C8—C10B	1.439 (7)	C18—N2	1.363 (3)
C8—C10A	1.465 (6)	C18—C19	1.505 (3)
C8—H8A	0.9800	C19—C21	1.510 (3)
C8—H8B	0.9815	C19—C20	1.512 (4)
C9—H9A	0.9600	C19—H19	0.9800
C9—H9B	0.9600	C20—H20A	0.9600
C9—H9C	0.9600	C20—H20B	0.9600
C10A—H10A	0.9600	C20—H20C	0.9600
C10A—H10B	0.9600	C21—H21A	0.9600
C10A—H10C	0.9600	C21—H21B	0.9600
C10B—H8A	1.2021	C21—H21C	0.9600
C10B—H8B	1.0050	C22—H22A	0.9600
C10B—H10D	0.9600	C22—H22B	0.9600
C10B—H10E	0.9600	C22—H22C	0.9600
C10B—H10F	0.9600	N2—S2	1.6594 (18)
C11—H11A	0.9600	N2—H2N	0.809 (15)
C11—H11B	0.9600	O4—S2	1.4191 (17)
C11—H11C	0.9600	O5—S2	1.4230 (18)
N1—S1	1.6530 (19)

C6—C1—C2	121.9 (2)	C2—C11—H11C	109.5
C6—C1—S1	116.01 (16)	H11A—C11—H11C	109.5
C2—C1—S1	121.86 (17)	H11B—C11—H11C	109.5
C3—C2—C1	116.5 (2)	C7—N1—S1	124.78 (15)
C3—C2—C11	119.4 (2)	C7—N1—H1N	119.0 (17)
C1—C2—C11	124.1 (2)	S1—N1—H1N	116.0 (17)
C4—C3—C2	122.1 (3)	O1—S1—O2	119.96 (13)
C4—C3—H3	119.0	O1—S1—N1	104.00 (11)
C2—C3—H3	119.0	O2—S1—N1	108.46 (10)
C3—C4—C5	121.3 (3)	O1—S1—C1	108.94 (11)
C3—C4—H4	119.4	O2—S1—C1	108.20 (11)
C5—C4—H4	119.4	N1—S1—C1	106.49 (9)
C4—C5—C6	119.0 (3)	C17—C12—C13	121.7 (2)
C4—C5—H5	120.5	C17—C12—S2	115.98 (19)
C6—C5—H5	120.5	C13—C12—S2	122.29 (19)
C1—C6—C5	119.2 (2)	C12—C13—C14	116.1 (3)
C1—C6—H6	120.4	C12—C13—C22	123.8 (2)
C5—C6—H6	120.4	C14—C13—C22	120.1 (3)
O3—C7—N1	121.4 (2)	C15—C14—C13	122.0 (3)
O3—C7—C8	122.5 (2)	C15—C14—H14	119.0
N1—C7—C8	116.1 (2)	C13—C14—H14	119.0
C9—C8—C10B	124.9 (5)	C14—C15—C16	121.3 (3)
C9—C8—C10A	125.5 (4)	C14—C15—H15	119.4
C10B—C8—C10A	39.5 (4)	C16—C15—H15	119.4
C9—C8—C7	115.8 (3)	C15—C16—C17	118.9 (3)
C10B—C8—C7	116.8 (5)	C15—C16—H16	120.6
C10A—C8—C7	112.2 (3)	C17—C16—H16	120.6
C9—C8—H8A	100.1	C12—C17—C16	120.2 (3)
C10B—C8—H8A	55.8	C12—C17—H17	119.9
C10A—C8—H8A	95.2	C16—C17—H17	119.9
C7—C8—H8A	100.1	O6—C18—N2	120.2 (2)
C9—C8—H8B	104.4	O6—C18—C19	124.29 (19)
C10B—C8—H8B	44.2	N2—C18—C19	115.47 (17)
C10A—C8—H8B	83.7	C18—C19—C21	110.9 (2)
C7—C8—H8B	107.5	C18—C19—C20	108.4 (2)
H8A—C8—H8B	11.9	C21—C19—C20	112.2 (2)
C8—C9—H9A	109.5	C18—C19—H19	108.4
C8—C9—H9B	109.5	C21—C19—H19	108.4
H9A—C9—H9B	109.5	C20—C19—H19	108.4
C8—C9—H9C	109.5	C19—C20—H20A	109.5
H9A—C9—H9C	109.5	C19—C20—H20B	109.5
H9B—C9—H9C	109.5	H20A—C20—H20B	109.5
C8—C10A—H10A	109.5	C19—C20—H20C	109.5
C8—C10A—H10B	109.5	H20A—C20—H20C	109.5
H10A—C10A—H10B	109.5	H20B—C20—H20C	109.5
C8—C10A—H10C	109.5	C19—C21—H21A	109.5
H10A—C10A—H10C	109.5	C19—C21—H21B	109.5
H10B—C10A—H10C	109.5	H21A—C21—H21B	109.5
C8—C10B—H8A	42.4	C19—C21—H21C	109.5
C8—C10B—H8B	42.9	H21A—C21—H21C	109.5
H8A—C10B—H8B	2.7	H21B—C21—H21C	109.5
C8—C10B—H10D	109.5	C13—C22—H22A	109.5
H8A—C10B—H10D	107.3	C13—C22—H22B	109.5
H8B—C10B—H10D	104.5	H22A—C22—H22B	109.5
C8—C10B—H10E	109.5	C13—C22—H22C	109.5
H8A—C10B—H10E	70.9	H22A—C22—H22C	109.5
H8B—C10B—H10E	71.6	H22B—C22—H22C	109.5
H10D—C10B—H10E	109.5	C18—N2—S2	124.90 (14)
C8—C10B—H10F	109.5	C18—N2—H2N	120.5 (17)
H8A—C10B—H10F	140.3	S2—N2—H2N	113.7 (17)
H8B—C10B—H10F	142.8	O4—S2—O5	119.32 (12)
H10D—C10B—H10F	109.5	O4—S2—N2	108.92 (10)
H10E—C10B—H10F	109.5	O5—S2—N2	103.66 (10)
C2—C11—H11A	109.5	O4—S2—C12	108.15 (11)
C2—C11—H11B	109.5	O5—S2—C12	110.02 (11)
H11A—C11—H11B	109.5	N2—S2—C12	105.94 (10)

C6—C1—C2—C3	−0.5 (3)	C2—C1—S1—N1	−58.61 (19)
S1—C1—C2—C3	−174.84 (18)	C17—C12—C13—C14	2.2 (4)
C6—C1—C2—C11	178.5 (2)	S2—C12—C13—C14	178.89 (19)
S1—C1—C2—C11	4.1 (3)	C17—C12—C13—C22	−177.4 (3)
C1—C2—C3—C4	0.4 (4)	S2—C12—C13—C22	−0.7 (3)
C11—C2—C3—C4	−178.7 (3)	C12—C13—C14—C15	−1.7 (4)
C2—C3—C4—C5	−0.3 (5)	C22—C13—C14—C15	177.9 (3)
C3—C4—C5—C6	0.2 (5)	C13—C14—C15—C16	0.0 (5)
C2—C1—C6—C5	0.5 (4)	C14—C15—C16—C17	1.2 (5)
S1—C1—C6—C5	175.1 (2)	C13—C12—C17—C16	−1.1 (4)
C4—C5—C6—C1	−0.3 (5)	S2—C12—C17—C16	−178.0 (2)
O3—C7—C8—C9	−96.8 (4)	C15—C16—C17—C12	−0.7 (5)
N1—C7—C8—C9	84.1 (4)	O6—C18—C19—C21	44.9 (3)
O3—C7—C8—C10B	100.0 (8)	N2—C18—C19—C21	−137.2 (2)
N1—C7—C8—C10B	−79.1 (8)	O6—C18—C19—C20	−78.7 (3)
O3—C7—C8—C10A	56.6 (8)	N2—C18—C19—C20	99.2 (2)
N1—C7—C8—C10A	−122.5 (7)	O6—C18—N2—S2	−7.8 (3)
O3—C7—N1—S1	1.1 (3)	C19—C18—N2—S2	174.15 (16)
C8—C7—N1—S1	−179.8 (2)	C18—N2—S2—O4	−52.3 (2)
C7—N1—S1—O1	177.60 (19)	C18—N2—S2—O5	179.70 (18)
C7—N1—S1—O2	48.9 (2)	C18—N2—S2—C12	63.9 (2)
C7—N1—S1—C1	−67.4 (2)	C17—C12—S2—O4	−9.3 (2)
C6—C1—S1—O1	−121.66 (19)	C13—C12—S2—O4	173.83 (19)
C2—C1—S1—O1	53.0 (2)	C17—C12—S2—O5	122.6 (2)
C6—C1—S1—O2	10.3 (2)	C13—C12—S2—O5	−54.3 (2)
C2—C1—S1—O2	−175.03 (17)	C17—C12—S2—N2	−125.97 (19)
C6—C1—S1—N1	126.72 (17)	C13—C12—S2—N2	57.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6	0.82 (2)	2.02 (2)	2.844 (2)	175 (2)
N2—H2N···O3ⁱ	0.81 (2)	2.08 (2)	2.870 (2)	167 (2)

Symmetry code: (i) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅NO₃S
M_r	241.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.829 (1), 16.351 (1), 13.351 (1)
β (°)	96.485 (8)
V (Å³)	2565.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.46 × 0.44 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.896, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	9793, 5225, 3538
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.06
No. of reflections	5225
No. of parameters	306
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6	0.824 (16)	2.022 (16)	2.844 (2)	175 (2)
N2—H2N···O3ⁱ	0.809 (15)	2.076 (16)	2.870 (2)	167 (2)

Symmetry code: (i) x−1/2, −y+3/2, z+1/2.

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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