2,2-Dimethyl-N-(2-methyl-phenyl-sulfon-yl)acetamide.

The asymmetric unit of the title compound, C(11)H(15)NO(3)S, contains two independent mol-ecules 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 mol-ecules. In one of the mol-ecules, 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, mol-ecules 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. (2011 ▶)

Experimental

Crystal data

C11H15NO3S

M = 241.30

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.06

5225 reflections

306 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027838/bt5569sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811027838/bt5569Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15NO3S	F(000) = 1024
Mr = 241.30	Dx = 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

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

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(Fo2) + (0.0663P)2 + 0.310P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5225 reflections	Δρmax = 0.25 e Å−3
306 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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)

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) .