3-(4-Chloro-benzene-sulfonamido)-5-methyl-cyclo-hex-2-en-1-one.

For the title compound, C(13)H(14)ClNO(3)S, geometrical parameters, determined using X-ray diffraction techniques, are compared with those calculated by density functional theory (DFT), using hybrid exchange-correlation functional, B3LYP methods. The dihedral angle between the benzene ring and the conjugated part of the cyclo-hexene ring is 87.47 (5)°. The cyclo-hexene ring and its substituents are disordered over two conformations, with occupancies of 0.786 (3) and 0.214 (3). In the crystal, mol-ecules are linked into chains in the c-axis direction by inter-molecular N-H⋯O(C=O) hydrogen bonds. C-H⋯O inter-actions are also observed.

Related literature

For the crystal growth of the title compound, see: Assey (2010 ▶). For related enaminone structures and properties, see: Edafiogho et al. (2006 ▶, 2007 ▶); Eddington et al. (2000 ▶); Jackson (2009 ▶); Michael et al. (1996 ▶, 2001 ▶). For their anti-convulsant activity, see: Stables & Kupferburg (1997 ▶). For information related to GAUSSIAN software, see: Frisch et al. (2004 ▶)

Experimental

Crystal data

C13H14ClNO3S

M = 299.76

Monoclinic,

a = 10.2031 (2) Å

b = 10.3267 (3) Å

c = 14.1217 (3) Å

β = 108.989 (3)°

V = 1406.95 (6) Å3

Z = 4

Cu Kα radiation

μ = 3.83 mm−1

T = 295 K

0.76 × 0.61 × 0.31 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.119, T max = 0.355

5137 measured reflections

2778 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.250

S = 1.07

2778 reflections

205 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.26 e Å−3

Δρmin = −0.65 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030662/hg5071sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030662/hg5071Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030662/hg5071Isup3.cml

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

C13H14ClNO3S	F(000) = 624
Mr = 299.76	Dx = 1.415 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4047 reflections
a = 10.2031 (2) Å	θ = 4.3–77.2°
b = 10.3267 (3) Å	µ = 3.83 mm−1
c = 14.1217 (3) Å	T = 295 K
β = 108.989 (3)°	Large plate, colorless
V = 1406.95 (6) Å3	0.76 × 0.61 × 0.31 mm
Z = 4

Oxford Diffraction Gemini R diffractometer	2778 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 10.5081 pixels mm-1	θmax = 77.7°, θmin = 4.6°
φ and ω scans	h = −12→11
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −11→12
Tmin = 0.119, Tmax = 0.355	l = −17→16
5137 measured reflections

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)] = 0.083	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.250	w = 1/[σ2(Fo2) + (0.183P)2 + 0.6772P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2778 reflections	Δρmax = 1.26 e Å−3
205 parameters	Δρmin = −0.65 e Å−3
18 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: 0.0074 (13)

Experimental. CrysAlis RED (Oxford Diffraction , 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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)
Cl	1.22572 (8)	0.52485 (10)	0.58620 (7)	0.0804 (3)
S	0.75611 (6)	0.92036 (5)	0.56637 (4)	0.04691 (16)
O1	0.7602 (2)	1.02174 (17)	0.49885 (16)	0.0609 (5)
O2	0.7649 (2)	0.9502 (2)	0.66719 (15)	0.0706 (6)
N	0.60950 (18)	0.84131 (18)	0.52132 (10)	0.0412 (4)
H1N	0.591 (2)	0.802 (2)	0.5668 (14)	0.048 (7)*
C1	0.8877 (2)	0.8073 (2)	0.56969 (17)	0.0441 (5)
C2	0.9599 (3)	0.8170 (3)	0.5024 (2)	0.0538 (6)
H2A	0.9385	0.8817	0.4540	0.065*
C3	1.0638 (3)	0.7296 (3)	0.5081 (2)	0.0605 (7)
H3A	1.1137	0.7351	0.4636	0.073*
C4	1.0935 (2)	0.6346 (3)	0.5792 (2)	0.0557 (7)
C5	1.0217 (3)	0.6238 (3)	0.6468 (2)	0.0596 (7)
H5A	1.0433	0.5585	0.6948	0.072*
C6	0.9181 (2)	0.7110 (3)	0.64169 (19)	0.0534 (6)
H6A	0.8686	0.7054	0.6864	0.064*
O3A'	0.5775 (3)	0.8028 (3)	0.17833 (16)	0.0530 (5)	0.786 (3)
C1A'	0.5533 (3)	0.7962 (2)	0.42417 (12)	0.0339 (4)	0.786 (3)
C2A'	0.6036 (3)	0.8212 (3)	0.34828 (19)	0.0364 (5)	0.786 (3)
H2AA	0.6808	0.8745	0.3599	0.044*	0.786 (3)
C3A'	0.5401 (3)	0.7671 (3)	0.2502 (2)	0.0393 (5)	0.786 (3)
C4A'	0.4276 (3)	0.6688 (3)	0.2359 (2)	0.0466 (7)	0.786 (3)
H4AA	0.4685	0.5832	0.2497	0.056*	0.786 (3)
H4AB	0.3677	0.6704	0.1666	0.056*	0.786 (3)
C5A'	0.3411 (3)	0.6942 (3)	0.3040 (2)	0.0437 (7)	0.786 (3)
H5AA	0.2954	0.7784	0.2855	0.052*	0.786 (3)
C6A'	0.4363 (3)	0.7032 (3)	0.4122 (2)	0.0421 (6)	0.786 (3)
H6AA	0.3828	0.7308	0.4542	0.051*	0.786 (3)
H6AB	0.4738	0.6181	0.4347	0.051*	0.786 (3)
C7A'	0.2296 (4)	0.5931 (4)	0.2902 (3)	0.0558 (9)	0.786 (3)
H7AA	0.1709	0.5922	0.2215	0.084*	0.786 (3)
H7AB	0.1753	0.6132	0.3324	0.084*	0.786 (3)
H7AC	0.2718	0.5096	0.3079	0.084*	0.786 (3)
O3B'	0.5921 (10)	0.7747 (12)	0.1904 (6)	0.0530 (5)	0.214 (3)
C1B'	0.5549 (9)	0.7864 (5)	0.4272 (2)	0.0339 (4)	0.214 (3)
C2B'	0.5841 (11)	0.8367 (12)	0.3478 (6)	0.0364 (5)	0.214 (3)
H2BA	0.6405	0.9093	0.3552	0.044*	0.214 (3)
C3B'	0.5260 (10)	0.7750 (12)	0.2512 (7)	0.0393 (5)	0.214 (3)
C4B'	0.3941 (10)	0.7012 (12)	0.2334 (7)	0.0466 (7)	0.214 (3)
H4BA	0.3842	0.6399	0.1795	0.056*	0.214 (3)
H4BB	0.3169	0.7612	0.2119	0.056*	0.214 (3)
C5B'	0.3867 (10)	0.6284 (10)	0.3246 (6)	0.0437 (7)	0.214 (3)
H5BA	0.4570	0.5600	0.3395	0.052*	0.214 (3)
C6B'	0.4207 (11)	0.7179 (13)	0.4147 (8)	0.0421 (6)	0.214 (3)
H6BA	0.3470	0.7808	0.4053	0.051*	0.214 (3)
H6BB	0.4282	0.6680	0.4744	0.051*	0.214 (3)
C7B'	0.2415 (16)	0.5623 (17)	0.3043 (14)	0.0558 (9)	0.214 (3)
H7BA	0.1711	0.6277	0.2920	0.084*	0.214 (3)
H7BB	0.2423	0.5120	0.3617	0.084*	0.214 (3)
H7BC	0.2225	0.5068	0.2469	0.084*	0.214 (3)

	U11	U22	U33	U12	U13	U23
Cl	0.0536 (4)	0.0905 (5)	0.0885 (6)	0.0121 (3)	0.0112 (4)	−0.0009 (4)
S	0.0462 (3)	0.0526 (3)	0.0352 (3)	−0.0116 (2)	0.0040 (2)	−0.00969 (19)
O1	0.0640 (10)	0.0465 (9)	0.0670 (11)	−0.0130 (8)	0.0142 (8)	0.0008 (8)
O2	0.0764 (12)	0.0880 (12)	0.0396 (9)	−0.0123 (11)	0.0081 (8)	−0.0268 (9)
N	0.0399 (8)	0.0581 (10)	0.0253 (7)	−0.0102 (7)	0.0103 (6)	−0.0050 (7)
C1	0.0329 (9)	0.0557 (11)	0.0368 (10)	−0.0111 (8)	0.0019 (8)	0.0004 (8)
C2	0.0531 (11)	0.0599 (13)	0.0486 (12)	−0.0120 (10)	0.0170 (10)	0.0062 (10)
C3	0.0536 (12)	0.0721 (16)	0.0600 (14)	−0.0106 (12)	0.0243 (10)	0.0014 (12)
C4	0.0339 (10)	0.0649 (14)	0.0592 (14)	−0.0056 (10)	0.0026 (9)	−0.0020 (12)
C5	0.0433 (11)	0.0763 (16)	0.0511 (13)	−0.0075 (11)	0.0044 (10)	0.0162 (12)
C6	0.0404 (10)	0.0725 (15)	0.0426 (11)	−0.0100 (10)	0.0070 (9)	0.0114 (10)
O3A'	0.0683 (9)	0.0686 (13)	0.0278 (8)	−0.0041 (9)	0.0235 (7)	0.0011 (7)
C1A'	0.0317 (8)	0.0430 (9)	0.0264 (8)	−0.0005 (7)	0.0083 (6)	0.0000 (7)
C2A'	0.0329 (9)	0.0498 (11)	0.0272 (9)	−0.0061 (9)	0.0108 (7)	−0.0035 (8)
C3A'	0.0405 (10)	0.0513 (11)	0.0274 (9)	0.0008 (9)	0.0129 (8)	−0.0024 (8)
C4A'	0.0476 (14)	0.0558 (16)	0.0347 (11)	−0.0052 (12)	0.0112 (10)	−0.0115 (10)
C5A'	0.0333 (11)	0.0538 (15)	0.0403 (13)	−0.0072 (10)	0.0071 (9)	−0.0063 (11)
C6A'	0.0367 (10)	0.0599 (13)	0.0313 (9)	−0.0072 (9)	0.0132 (8)	0.0001 (9)
C7A'	0.0404 (11)	0.0595 (19)	0.0639 (17)	−0.0150 (12)	0.0122 (11)	−0.0074 (14)
O3B'	0.0683 (9)	0.0686 (13)	0.0278 (8)	−0.0041 (9)	0.0235 (7)	0.0011 (7)
C1B'	0.0317 (8)	0.0430 (9)	0.0264 (8)	−0.0005 (7)	0.0083 (6)	0.0000 (7)
C2B'	0.0329 (9)	0.0498 (11)	0.0272 (9)	−0.0061 (9)	0.0108 (7)	−0.0035 (8)
C3B'	0.0405 (10)	0.0513 (11)	0.0274 (9)	0.0008 (9)	0.0129 (8)	−0.0024 (8)
C4B'	0.0476 (14)	0.0558 (16)	0.0347 (11)	−0.0052 (12)	0.0112 (10)	−0.0115 (10)
C5B'	0.0333 (11)	0.0538 (15)	0.0403 (13)	−0.0072 (10)	0.0071 (9)	−0.0063 (11)
C6B'	0.0367 (10)	0.0599 (13)	0.0313 (9)	−0.0072 (9)	0.0132 (8)	0.0001 (9)
C7B'	0.0404 (11)	0.0595 (19)	0.0639 (17)	−0.0150 (12)	0.0122 (11)	−0.0074 (14)

Cl—C4	1.740 (3)	C4A'—H4AB	0.9700
S—O1	1.426 (2)	C5A'—C7A'	1.509 (5)
S—O2	1.431 (2)	C5A'—C6A'	1.524 (4)
S—N	1.6400 (17)	C5A'—H5AA	0.9800
S—C1	1.768 (2)	C6A'—H6AA	0.9700
N—C1B'	1.384 (2)	C6A'—H6AB	0.9700
N—C1A'	1.3843 (18)	C7A'—H7AA	0.9600
N—H1N	0.833 (16)	C7A'—H7AB	0.9600
C1—C2	1.382 (4)	C7A'—H7AC	0.9600
C1—C6	1.383 (3)	O3B'—C3B'	1.252 (12)
C2—C3	1.375 (4)	C1B'—C2B'	1.355 (10)
C2—H2A	0.9300	C1B'—C6B'	1.499 (11)
C3—C4	1.365 (4)	C2B'—C3B'	1.446 (11)
C3—H3A	0.9300	C2B'—H2BA	0.9300
C4—C5	1.384 (4)	C3B'—C4B'	1.494 (12)
C5—C6	1.373 (4)	C4B'—C5B'	1.514 (12)
C5—H5A	0.9300	C4B'—H4BA	0.9700
C6—H6A	0.9300	C4B'—H4BB	0.9700
O3A'—C3A'	1.251 (4)	C5B'—C6B'	1.519 (12)
C1A'—C2A'	1.356 (4)	C5B'—C7B'	1.570 (18)
C1A'—C6A'	1.498 (4)	C5B'—H5BA	0.9800
C2A'—C3A'	1.437 (3)	C6B'—H6BA	0.9700
C2A'—H2AA	0.9300	C6B'—H6BB	0.9700
C3A'—C4A'	1.496 (4)	C7B'—H7BA	0.9600
C4A'—C5A'	1.525 (4)	C7B'—H7BB	0.9600
C4A'—H4AA	0.9700	C7B'—H7BC	0.9600
O1—S—O2	120.11 (14)	C7A'—C5A'—C4A'	111.5 (3)
O1—S—N	109.11 (10)	C6A'—C5A'—C4A'	109.4 (2)
O2—S—N	104.28 (12)	C7A'—C5A'—H5AA	107.8
O1—S—C1	108.39 (12)	C6A'—C5A'—H5AA	107.8
O2—S—C1	108.34 (13)	C4A'—C5A'—H5AA	107.8
N—S—C1	105.70 (10)	C1A'—C6A'—C5A'	112.1 (2)
C1B'—N—S	127.4 (4)	C1A'—C6A'—H6AA	109.2
C1A'—N—S	125.70 (16)	C5A'—C6A'—H6AA	109.2
C1B'—N—H1N	114.7 (17)	C1A'—C6A'—H6AB	109.2
C1A'—N—H1N	118.3 (16)	C5A'—C6A'—H6AB	109.2
S—N—H1N	110.6 (15)	H6AA—C6A'—H6AB	107.9
C2—C1—C6	121.0 (2)	C2B'—C1B'—N	120.6 (6)
C2—C1—S	120.28 (19)	C2B'—C1B'—C6B'	121.5 (6)
C6—C1—S	118.7 (2)	N—C1B'—C6B'	112.0 (6)
C3—C2—C1	119.1 (2)	C1B'—C2B'—C3B'	118.6 (9)
C3—C2—H2A	120.5	C1B'—C2B'—H2BA	120.7
C1—C2—H2A	120.5	C3B'—C2B'—H2BA	120.7
C4—C3—C2	119.8 (3)	O3B'—C3B'—C2B'	120.0 (9)
C4—C3—H3A	120.1	O3B'—C3B'—C4B'	122.7 (9)
C2—C3—H3A	120.1	C2B'—C3B'—C4B'	117.0 (9)
C3—C4—C5	121.7 (3)	C3B'—C4B'—C5B'	113.7 (8)
C3—C4—Cl	119.5 (2)	C3B'—C4B'—H4BA	108.8
C5—C4—Cl	118.9 (2)	C5B'—C4B'—H4BA	108.8
C6—C5—C4	118.8 (3)	C3B'—C4B'—H4BB	108.8
C6—C5—H5A	120.6	C5B'—C4B'—H4BB	108.8
C4—C5—H5A	120.6	H4BA—C4B'—H4BB	107.7
C5—C6—C1	119.7 (3)	C4B'—C5B'—C6B'	110.5 (9)
C5—C6—H6A	120.2	C4B'—C5B'—C7B'	111.5 (9)
C1—C6—H6A	120.2	C6B'—C5B'—C7B'	111.2 (10)
C2A'—C1A'—N	125.3 (2)	C4B'—C5B'—H5BA	107.8
C2A'—C1A'—C6A'	121.7 (2)	C6B'—C5B'—H5BA	107.8
N—C1A'—C6A'	112.7 (2)	C7B'—C5B'—H5BA	107.8
C1A'—C2A'—C3A'	121.3 (2)	C1B'—C6B'—C5B'	109.7 (8)
C1A'—C2A'—H2AA	119.4	C1B'—C6B'—H6BA	109.7
C3A'—C2A'—H2AA	119.4	C5B'—C6B'—H6BA	109.7
O3A'—C3A'—C2A'	120.4 (3)	C1B'—C6B'—H6BB	109.7
O3A'—C3A'—C4A'	120.9 (2)	C5B'—C6B'—H6BB	109.7
C2A'—C3A'—C4A'	118.7 (3)	H6BA—C6B'—H6BB	108.2
C3A'—C4A'—C5A'	111.9 (2)	C5B'—C7B'—H7BA	109.5
C3A'—C4A'—H4AA	109.2	C5B'—C7B'—H7BB	109.5
C5A'—C4A'—H4AA	109.2	H7BA—C7B'—H7BB	109.5
C3A'—C4A'—H4AB	109.2	C5B'—C7B'—H7BC	109.5
C5A'—C4A'—H4AB	109.2	H7BA—C7B'—H7BC	109.5
H4AA—C4A'—H4AB	107.9	H7BB—C7B'—H7BC	109.5
C7A'—C5A'—C6A'	112.3 (3)
O1—S—N—C1B'	53.1 (4)	C6A'—C1A'—C2A'—C3A'	4.8 (4)
O2—S—N—C1B'	−177.4 (4)	C1A'—C2A'—C3A'—O3A'	171.7 (3)
C1—S—N—C1B'	−63.2 (4)	C1A'—C2A'—C3A'—C4A'	−7.5 (4)
O1—S—N—C1A'	48.0 (2)	O3A'—C3A'—C4A'—C5A'	−146.2 (3)
O2—S—N—C1A'	177.5 (2)	C2A'—C3A'—C4A'—C5A'	33.0 (4)
C1—S—N—C1A'	−68.4 (2)	C3A'—C4A'—C5A'—C7A'	−178.9 (3)
O1—S—C1—C2	−9.0 (2)	C3A'—C4A'—C5A'—C6A'	−54.2 (3)
O2—S—C1—C2	−140.8 (2)	C2A'—C1A'—C6A'—C5A'	−27.7 (4)
N—S—C1—C2	107.90 (19)	N—C1A'—C6A'—C5A'	158.0 (2)
O1—S—C1—C6	169.99 (18)	C7A'—C5A'—C6A'—C1A'	175.5 (3)
O2—S—C1—C6	38.1 (2)	C4A'—C5A'—C6A'—C1A'	51.3 (3)
N—S—C1—C6	−73.15 (19)	C1A'—N—C1B'—C2B'	40 (5)
C6—C1—C2—C3	−0.4 (4)	S—N—C1B'—C2B'	−28.9 (10)
S—C1—C2—C3	178.6 (2)	C1A'—N—C1B'—C6B'	−113 (6)
C1—C2—C3—C4	0.4 (4)	S—N—C1B'—C6B'	177.9 (6)
C2—C3—C4—C5	−0.2 (4)	N—C1B'—C2B'—C3B'	179.2 (8)
C2—C3—C4—Cl	−179.7 (2)	C6B'—C1B'—C2B'—C3B'	−30.1 (15)
C3—C4—C5—C6	0.0 (4)	C1B'—C2B'—C3B'—O3B'	−147.4 (12)
Cl—C4—C5—C6	179.5 (2)	C1B'—C2B'—C3B'—C4B'	26.1 (16)
C4—C5—C6—C1	0.0 (4)	O3B'—C3B'—C4B'—C5B'	135.8 (12)
C2—C1—C6—C5	0.2 (4)	C2B'—C3B'—C4B'—C5B'	−37.6 (15)
S—C1—C6—C5	−178.8 (2)	C3B'—C4B'—C5B'—C6B'	51.1 (13)
C1B'—N—C1A'—C2A'	−121 (6)	C3B'—C4B'—C5B'—C7B'	175.3 (11)
S—N—C1A'—C2A'	−6.9 (4)	C2B'—C1B'—C6B'—C5B'	43.2 (13)
C1B'—N—C1A'—C6A'	53 (6)	N—C1B'—C6B'—C5B'	−163.8 (7)
S—N—C1A'—C6A'	167.16 (19)	C4B'—C5B'—C6B'—C1B'	−51.6 (11)
N—C1A'—C2A'—C3A'	178.3 (3)	C7B'—C5B'—C6B'—C1B'	−175.9 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O3B'i	0.83 (2)	1.91 (2)	2.729 (10)	166 (2)
N—H1N···O3A'i	0.83 (2)	1.95 (2)	2.777 (3)	171 (2)
C5—H5A···O2ii	0.93	2.53	3.337 (3)	145.

Parameters	X-ray	DFT/B3LYP(3-21G**)
Cl—C4	1.7404 (12)	1.7556
S—O1	1.4262 (9)	1.4610
S—O2	1.4300 (9)	1.4613
S—N	1.6397 (7)	1.6831
S—C1	1.7675 (10)	1.7663
N—C1A'	1.4049 (11)	1.4055
O3A'—C3A'	1.2376 (14)	1.2415
C5A'—C7A'	1.5102 (18)	1.5477
O1—S—O2	120.12 (5)	123.44
O1—S—N	109.07 (4)	108.92
O2—S—N	104.34 (5)	103.61
O1—S—C1	108.40 (5)	107.79
O2—S—C1	108.31 (5)	108.21
N—S—C1	105.69 (4)	103.02
C6—C1—C2	120.93 (9)	121.18
C6—C1—S	118.79 (8)	120.04
C3—C4—C5	121.65 (11)	121.58
C3—C4—Cl	119.40 (10)	119.14
C5—C4—Cl	118.95 (9)	119.28
C2A'—C1A'—C6A'	122.58 (8)	122.53
C7A'—C5A'—C4A'	110.73 (11)	111.36
C1—S—N—C1A'	-67.84 (8)	76.42
N—S—C1—C6	-73.16 (8)	88.67
N—S—C1—C2	107.82 (8)	-92.03
S—N—C1A'—C2A'	-8.93 (14)	13.37

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H1N⋯O3B′i	0.83 (2)	1.91 (2)	2.729 (10)	166 (2)
N—H1N⋯O3A′i	0.83 (2)	1.95 (2)	2.777 (3)	171 (2)
C5—H5A⋯O2ii	0.93	2.53	3.337 (3)	145

Symmetry codes: (i) ; (ii) .