4-Chloro-N-(2,3-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

The asymmetric unit of the title compound, C(15)H(16)ClNO(2)S, contains two independent moleules. The conformation of the N-H bonds are anti to the ortho-methyl groups in the sulfonyl benzene rings of both the mol-ecules, while the N-H bonds are anti to the ortho- and meta-methyl groups in the aniline ring of one of the mol-ecules and syn in the other. Furthermore, the torsion angles of the C-SO(2)-NH-C segments in the two mol-ecules of are -66.8 (3) and 70.3 (3)°. The sulfonyl and the aniline benzene rings are oriented at angles of 44.1 (1) and 39.7 (1)° in the two mol-ecules. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of n class="Chemical">sulfonamides, see; Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (2006 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Gowda et al. (2010 ▶).

Experimental

Crystal data

C15H16ClNO2S

M = 309.80

Triclinic,

a = 8.2747 (7) Å

b = 11.0464 (9) Å

c = 17.021 (1) Å

α = 82.722 (7)°

β = 79.529 (7)°

γ = 80.267 (7)°

V = 1500.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.40 × 0.28 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.858, T max = 0.947

10437 measured reflections

6064 independent reflections

4140 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.166

S = 1.12

6064 reflections

373 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S1600536811037536/bq2304sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037536/bq2304Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037536/bq2304Isup3.cml

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

C15H16ClNO2S	Z = 4
Mr = 309.80	F(000) = 648
Triclinic, P1	Dx = 1.371 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2747 (7) Å	Cell parameters from 3482 reflections
b = 11.0464 (9) Å	θ = 2.5–27.9°
c = 17.021 (1) Å	µ = 0.39 mm−1
α = 82.722 (7)°	T = 293 K
β = 79.529 (7)°	Prism, light pink
γ = 80.267 (7)°	0.40 × 0.28 × 0.14 mm
V = 1500.5 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	6064 independent reflections
Radiation source: fine-focus sealed tube	4140 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→10
Tmin = 0.858, Tmax = 0.947	k = −13→13
10437 measured reflections	l = −20→21

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0505P)2 + 1.8811P] where P = (Fo2 + 2Fc2)/3
6064 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.58 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

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
Cl1	0.52306 (16)	1.04270 (13)	0.11188 (11)	0.1031 (5)
S1	0.01951 (12)	0.67472 (8)	0.25114 (5)	0.0460 (2)
O1	−0.1489 (3)	0.7348 (2)	0.26297 (15)	0.0552 (7)
O2	0.0856 (4)	0.6027 (2)	0.31763 (14)	0.0610 (7)
N1	0.0393 (4)	0.5780 (3)	0.18362 (17)	0.0443 (7)
H1N	0.134 (3)	0.533 (3)	0.182 (2)	0.053*
C1	0.1528 (4)	0.7859 (3)	0.2117 (2)	0.0437 (8)
C2	0.1054 (4)	0.8924 (3)	0.1619 (2)	0.0494 (9)
C3	0.2245 (5)	0.9684 (3)	0.1318 (3)	0.0590 (10)
H3	0.1971	1.0392	0.0982	0.071*
C4	0.3823 (5)	0.9412 (4)	0.1508 (3)	0.0597 (10)
C5	0.4282 (5)	0.8370 (4)	0.2000 (3)	0.0608 (11)
H5	0.5349	0.8195	0.2127	0.073*
C6	0.3138 (5)	0.7598 (4)	0.2299 (2)	0.0519 (9)
H6	0.3436	0.6888	0.2629	0.062*
C7	−0.0170 (4)	0.6186 (3)	0.10819 (19)	0.0388 (7)
C8	0.0950 (4)	0.6401 (3)	0.0383 (2)	0.0422 (8)
C9	0.0315 (5)	0.6788 (3)	−0.0338 (2)	0.0495 (9)
C10	−0.1381 (5)	0.6941 (4)	−0.0326 (3)	0.0591 (10)
H10	−0.1795	0.7191	−0.0803	0.071*
C11	−0.2468 (5)	0.6733 (4)	0.0370 (3)	0.0597 (11)
H11	−0.3607	0.6858	0.0366	0.072*
C12	−0.1861 (4)	0.6338 (3)	0.1073 (2)	0.0501 (9)
H12	−0.2589	0.6172	0.1545	0.060*
C13	−0.0679 (5)	0.9320 (4)	0.1388 (3)	0.0660 (12)
H13A	−0.1452	0.9589	0.1848	0.079*
H13B	−0.1029	0.8634	0.1206	0.079*
H13C	−0.0641	0.9986	0.0967	0.079*
C14	0.2798 (4)	0.6235 (4)	0.0383 (2)	0.0569 (10)
H14A	0.3052	0.5743	0.0864	0.068*
H14B	0.3141	0.7028	0.0362	0.068*
H14C	0.3376	0.5830	−0.0076	0.068*
C15	0.1476 (6)	0.7027 (4)	−0.1115 (2)	0.0740 (13)
H15A	0.2166	0.6269	−0.1253	0.089*
H15B	0.2163	0.7615	−0.1052	0.089*
H15C	0.0839	0.7348	−0.1534	0.089*
Cl2	−0.09225 (15)	−0.06815 (12)	0.40474 (9)	0.0840 (4)
S2	0.39623 (11)	0.31016 (8)	0.26485 (5)	0.0461 (2)
O3	0.3263 (3)	0.3796 (2)	0.19847 (15)	0.0607 (7)
O4	0.5651 (3)	0.2535 (2)	0.25283 (15)	0.0579 (7)
N2	0.3740 (4)	0.4077 (3)	0.33141 (18)	0.0475 (7)
H2N	0.282 (3)	0.456 (3)	0.334 (2)	0.057*
C16	0.2681 (4)	0.1958 (3)	0.3046 (2)	0.0424 (8)
C17	0.3215 (5)	0.0878 (3)	0.3519 (2)	0.0489 (9)
C18	0.2057 (5)	0.0090 (3)	0.3816 (2)	0.0558 (10)
H18	0.2368	−0.0631	0.4133	0.067*
C19	0.0459 (5)	0.0349 (3)	0.3652 (2)	0.0518 (9)
C20	−0.0065 (5)	0.1399 (4)	0.3189 (2)	0.0556 (10)
H20	−0.1145	0.1562	0.3077	0.067*
C21	0.1047 (4)	0.2201 (4)	0.2893 (2)	0.0511 (9)
H21	0.0706	0.2924	0.2585	0.061*
C22	0.4406 (4)	0.3718 (3)	0.4052 (2)	0.0404 (7)
C23	0.6040 (4)	0.3884 (3)	0.4066 (2)	0.0408 (8)
C24	0.6675 (5)	0.3519 (3)	0.4783 (2)	0.0510 (9)
C25	0.5644 (6)	0.3059 (4)	0.5452 (2)	0.0649 (12)
H25	0.6061	0.2827	0.5929	0.078*
C26	0.4023 (6)	0.2936 (4)	0.5431 (2)	0.0649 (12)
H26	0.3358	0.2638	0.5891	0.078*
C27	0.3396 (5)	0.3256 (3)	0.4727 (2)	0.0524 (9)
H27	0.2309	0.3164	0.4703	0.063*
C28	0.4975 (5)	0.0499 (4)	0.3714 (3)	0.0690 (12)
H28A	0.5307	0.1174	0.3918	0.083*
H28B	0.5729	0.0287	0.3235	0.083*
H28C	0.4994	−0.0201	0.4111	0.083*
C29	0.7049 (5)	0.4485 (4)	0.3345 (2)	0.0571 (10)
H29A	0.6317	0.5008	0.3023	0.069*
H29B	0.7720	0.3861	0.3033	0.069*
H29C	0.7754	0.4971	0.3517	0.069*
C30	0.8441 (5)	0.3647 (5)	0.4836 (3)	0.0803 (15)
H30A	0.8636	0.4473	0.4642	0.096*
H30B	0.9199	0.3073	0.4515	0.096*
H30C	0.8610	0.3476	0.5385	0.096*

	U11	U22	U33	U12	U13	U23
Cl1	0.0637 (8)	0.0905 (9)	0.1610 (15)	−0.0338 (7)	−0.0213 (8)	−0.0007 (9)
S1	0.0517 (6)	0.0501 (5)	0.0345 (4)	−0.0050 (4)	−0.0070 (4)	−0.0013 (4)
O1	0.0483 (15)	0.0622 (16)	0.0507 (15)	−0.0037 (12)	0.0005 (12)	−0.0073 (12)
O2	0.0770 (19)	0.0663 (17)	0.0369 (13)	−0.0031 (14)	−0.0143 (13)	0.0025 (12)
N1	0.0492 (18)	0.0428 (17)	0.0386 (15)	−0.0028 (13)	−0.0090 (14)	0.0018 (13)
C1	0.0432 (19)	0.0454 (19)	0.0437 (19)	−0.0010 (15)	−0.0113 (16)	−0.0107 (15)
C2	0.044 (2)	0.0425 (19)	0.064 (2)	−0.0018 (16)	−0.0161 (18)	−0.0065 (17)
C3	0.053 (2)	0.044 (2)	0.082 (3)	−0.0069 (18)	−0.020 (2)	−0.001 (2)
C4	0.044 (2)	0.060 (2)	0.079 (3)	−0.0130 (18)	−0.011 (2)	−0.016 (2)
C5	0.044 (2)	0.070 (3)	0.074 (3)	0.000 (2)	−0.022 (2)	−0.023 (2)
C6	0.050 (2)	0.057 (2)	0.052 (2)	−0.0012 (18)	−0.0198 (18)	−0.0066 (18)
C7	0.0441 (19)	0.0356 (17)	0.0376 (17)	−0.0076 (14)	−0.0076 (15)	−0.0030 (14)
C8	0.0436 (19)	0.0409 (18)	0.0429 (19)	−0.0085 (15)	−0.0064 (15)	−0.0050 (15)
C9	0.067 (3)	0.046 (2)	0.0381 (19)	−0.0141 (18)	−0.0113 (17)	−0.0037 (15)
C10	0.070 (3)	0.057 (2)	0.057 (2)	−0.005 (2)	−0.031 (2)	−0.0062 (19)
C11	0.049 (2)	0.064 (3)	0.073 (3)	−0.0065 (19)	−0.025 (2)	−0.014 (2)
C12	0.045 (2)	0.054 (2)	0.053 (2)	−0.0141 (17)	−0.0053 (17)	−0.0083 (17)
C13	0.050 (2)	0.045 (2)	0.102 (3)	−0.0053 (18)	−0.030 (2)	0.017 (2)
C14	0.046 (2)	0.071 (3)	0.051 (2)	−0.0146 (19)	0.0008 (17)	−0.0053 (19)
C15	0.097 (4)	0.081 (3)	0.044 (2)	−0.026 (3)	−0.006 (2)	0.003 (2)
Cl2	0.0711 (8)	0.0751 (8)	0.1086 (10)	−0.0281 (6)	−0.0147 (7)	0.0035 (7)
S2	0.0475 (5)	0.0498 (5)	0.0412 (5)	−0.0046 (4)	−0.0127 (4)	−0.0012 (4)
O3	0.0714 (18)	0.0662 (17)	0.0443 (14)	−0.0072 (14)	−0.0201 (13)	0.0061 (13)
O4	0.0504 (16)	0.0676 (17)	0.0542 (16)	−0.0069 (13)	−0.0039 (12)	−0.0093 (13)
N2	0.0470 (18)	0.0454 (17)	0.0506 (17)	0.0005 (13)	−0.0177 (15)	−0.0029 (14)
C16	0.046 (2)	0.0422 (19)	0.0406 (18)	−0.0005 (15)	−0.0127 (15)	−0.0086 (15)
C17	0.049 (2)	0.045 (2)	0.054 (2)	0.0033 (16)	−0.0197 (18)	−0.0062 (17)
C18	0.060 (2)	0.044 (2)	0.064 (2)	−0.0040 (18)	−0.017 (2)	−0.0008 (18)
C19	0.051 (2)	0.051 (2)	0.056 (2)	−0.0090 (17)	−0.0104 (18)	−0.0110 (18)
C20	0.043 (2)	0.065 (3)	0.063 (2)	−0.0058 (18)	−0.0175 (19)	−0.007 (2)
C21	0.046 (2)	0.056 (2)	0.051 (2)	0.0028 (17)	−0.0205 (17)	−0.0029 (17)
C22	0.0439 (19)	0.0348 (17)	0.0418 (18)	−0.0046 (14)	−0.0056 (15)	−0.0050 (14)
C23	0.0441 (19)	0.0369 (17)	0.0418 (18)	−0.0088 (14)	−0.0051 (15)	−0.0044 (14)
C24	0.056 (2)	0.048 (2)	0.052 (2)	0.0047 (17)	−0.0185 (18)	−0.0169 (17)
C25	0.098 (4)	0.052 (2)	0.041 (2)	0.010 (2)	−0.022 (2)	−0.0056 (18)
C26	0.091 (3)	0.053 (2)	0.043 (2)	−0.012 (2)	0.008 (2)	0.0007 (18)
C27	0.055 (2)	0.049 (2)	0.052 (2)	−0.0155 (17)	0.0028 (18)	−0.0066 (17)
C28	0.052 (2)	0.055 (2)	0.098 (3)	0.0012 (19)	−0.032 (2)	0.015 (2)
C29	0.050 (2)	0.063 (2)	0.060 (2)	−0.0185 (19)	−0.0006 (19)	−0.0093 (19)
C30	0.061 (3)	0.098 (4)	0.090 (3)	0.011 (3)	−0.035 (3)	−0.036 (3)

Cl1—C4	1.739 (4)	Cl2—C19	1.738 (4)
S1—O1	1.429 (3)	S2—O4	1.421 (3)
S1—O2	1.436 (2)	S2—O3	1.438 (2)
S1—N1	1.635 (3)	S2—N2	1.626 (3)
S1—C1	1.777 (4)	S2—C16	1.776 (4)
N1—C7	1.438 (4)	N2—C22	1.445 (4)
N1—H1N	0.850 (18)	N2—H2N	0.848 (18)
C1—C6	1.396 (5)	C16—C21	1.398 (5)
C1—C2	1.403 (5)	C16—C17	1.405 (5)
C2—C3	1.387 (5)	C17—C18	1.388 (5)
C2—C13	1.533 (5)	C17—C28	1.530 (5)
C3—C4	1.377 (5)	C18—C19	1.376 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.376 (6)	C19—C20	1.371 (5)
C5—C6	1.368 (5)	C20—C21	1.371 (5)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C12	1.384 (5)	C22—C27	1.388 (5)
C7—C8	1.390 (5)	C22—C23	1.400 (5)
C8—C9	1.410 (5)	C23—C24	1.403 (5)
C8—C14	1.509 (5)	C23—C29	1.500 (5)
C9—C10	1.382 (5)	C24—C25	1.389 (6)
C9—C15	1.509 (5)	C24—C30	1.512 (6)
C10—C11	1.372 (6)	C25—C26	1.378 (6)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.374 (5)	C26—C27	1.374 (6)
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—H14A	0.9600	C29—H29A	0.9600
C14—H14B	0.9600	C29—H29B	0.9600
C14—H14C	0.9600	C29—H29C	0.9600
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600
O1—S1—O2	119.33 (16)	O4—S2—O3	119.65 (17)
O1—S1—N1	108.10 (16)	O4—S2—N2	107.93 (16)
O2—S1—N1	104.79 (15)	O3—S2—N2	104.94 (16)
O1—S1—C1	109.28 (16)	O4—S2—C16	109.10 (16)
O2—S1—C1	107.43 (17)	O3—S2—C16	106.85 (16)
N1—S1—C1	107.27 (16)	N2—S2—C16	107.82 (16)
C7—N1—S1	120.3 (2)	C22—N2—S2	120.5 (2)
C7—N1—H1N	117 (3)	C22—N2—H2N	118 (3)
S1—N1—H1N	109 (3)	S2—N2—H2N	112 (3)
C6—C1—C2	120.4 (3)	C21—C16—C17	120.1 (3)
C6—C1—S1	116.4 (3)	C21—C16—S2	116.5 (3)
C2—C1—S1	123.2 (3)	C17—C16—S2	123.3 (3)
C3—C2—C1	117.3 (3)	C18—C17—C16	117.0 (3)
C3—C2—C13	117.5 (3)	C18—C17—C28	118.0 (3)
C1—C2—C13	125.2 (3)	C16—C17—C28	124.9 (3)
C4—C3—C2	121.4 (4)	C19—C18—C17	121.6 (4)
C4—C3—H3	119.3	C19—C18—H18	119.2
C2—C3—H3	119.3	C17—C18—H18	119.2
C5—C4—C3	121.2 (4)	C20—C19—C18	121.6 (4)
C5—C4—Cl1	120.4 (3)	C20—C19—Cl2	119.5 (3)
C3—C4—Cl1	118.4 (3)	C18—C19—Cl2	119.0 (3)
C6—C5—C4	118.7 (4)	C19—C20—C21	118.1 (3)
C6—C5—H5	120.7	C19—C20—H20	120.9
C4—C5—H5	120.7	C21—C20—H20	120.9
C5—C6—C1	121.1 (4)	C20—C21—C16	121.5 (3)
C5—C6—H6	119.5	C20—C21—H21	119.2
C1—C6—H6	119.5	C16—C21—H21	119.2
C12—C7—C8	121.2 (3)	C27—C22—C23	122.2 (3)
C12—C7—N1	117.8 (3)	C27—C22—N2	119.2 (3)
C8—C7—N1	121.1 (3)	C23—C22—N2	118.6 (3)
C7—C8—C9	118.2 (3)	C22—C23—C24	117.9 (3)
C7—C8—C14	121.7 (3)	C22—C23—C29	120.8 (3)
C9—C8—C14	120.1 (3)	C24—C23—C29	121.3 (3)
C10—C9—C8	119.3 (4)	C25—C24—C23	118.9 (4)
C10—C9—C15	120.3 (4)	C25—C24—C30	120.3 (4)
C8—C9—C15	120.4 (4)	C23—C24—C30	120.8 (4)
C11—C10—C9	121.7 (4)	C26—C25—C24	122.2 (4)
C11—C10—H10	119.2	C26—C25—H25	118.9
C9—C10—H10	119.2	C24—C25—H25	118.9
C10—C11—C12	119.4 (4)	C27—C26—C25	119.6 (4)
C10—C11—H11	120.3	C27—C26—H26	120.2
C12—C11—H11	120.3	C25—C26—H26	120.2
C11—C12—C7	120.2 (4)	C26—C27—C22	119.0 (4)
C11—C12—H12	119.9	C26—C27—H27	120.5
C7—C12—H12	119.9	C22—C27—H27	120.5
C2—C13—H13A	109.5	C17—C28—H28A	109.5
C2—C13—H13B	109.5	C17—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28B	109.5
C2—C13—H13C	109.5	C17—C28—H28C	109.5
H13A—C13—H13C	109.5	H28A—C28—H28C	109.5
H13B—C13—H13C	109.5	H28B—C28—H28C	109.5
C8—C14—H14A	109.5	C23—C29—H29A	109.5
C8—C14—H14B	109.5	C23—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C8—C14—H14C	109.5	C23—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C9—C15—H15A	109.5	C24—C30—H30A	109.5
C9—C15—H15B	109.5	C24—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C9—C15—H15C	109.5	C24—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O1—S1—N1—C7	50.9 (3)	O4—S2—N2—C22	−47.4 (3)
O2—S1—N1—C7	179.2 (3)	O3—S2—N2—C22	−176.0 (3)
C1—S1—N1—C7	−66.8 (3)	C16—S2—N2—C22	70.3 (3)
O1—S1—C1—C6	151.7 (3)	O4—S2—C16—C21	−154.0 (3)
O2—S1—C1—C6	20.8 (3)	O3—S2—C16—C21	−23.3 (3)
N1—S1—C1—C6	−91.4 (3)	N2—S2—C16—C21	89.0 (3)
O1—S1—C1—C2	−31.0 (3)	O4—S2—C16—C17	28.5 (3)
O2—S1—C1—C2	−161.8 (3)	O3—S2—C16—C17	159.2 (3)
N1—S1—C1—C2	86.0 (3)	N2—S2—C16—C17	−88.4 (3)
C6—C1—C2—C3	0.5 (5)	C21—C16—C17—C18	0.0 (5)
S1—C1—C2—C3	−176.7 (3)	S2—C16—C17—C18	177.4 (3)
C6—C1—C2—C13	−178.9 (4)	C21—C16—C17—C28	178.8 (4)
S1—C1—C2—C13	3.8 (5)	S2—C16—C17—C28	−3.8 (5)
C1—C2—C3—C4	−0.7 (6)	C16—C17—C18—C19	0.4 (6)
C13—C2—C3—C4	178.7 (4)	C28—C17—C18—C19	−178.5 (4)
C2—C3—C4—C5	0.3 (7)	C17—C18—C19—C20	−0.1 (6)
C2—C3—C4—Cl1	−178.9 (3)	C17—C18—C19—Cl2	−179.9 (3)
C3—C4—C5—C6	0.3 (6)	C18—C19—C20—C21	−0.6 (6)
Cl1—C4—C5—C6	179.6 (3)	Cl2—C19—C20—C21	179.2 (3)
C4—C5—C6—C1	−0.5 (6)	C19—C20—C21—C16	1.0 (6)
C2—C1—C6—C5	0.1 (6)	C17—C16—C21—C20	−0.7 (6)
S1—C1—C6—C5	177.5 (3)	S2—C16—C21—C20	−178.3 (3)
S1—N1—C7—C12	−76.7 (4)	S2—N2—C22—C27	−92.8 (4)
S1—N1—C7—C8	104.2 (3)	S2—N2—C22—C23	89.1 (4)
C12—C7—C8—C9	0.5 (5)	C27—C22—C23—C24	2.7 (5)
N1—C7—C8—C9	179.5 (3)	N2—C22—C23—C24	−179.3 (3)
C12—C7—C8—C14	−179.8 (3)	C27—C22—C23—C29	−174.8 (3)
N1—C7—C8—C14	−0.8 (5)	N2—C22—C23—C29	3.2 (5)
C7—C8—C9—C10	0.0 (5)	C22—C23—C24—C25	−2.6 (5)
C14—C8—C9—C10	−179.7 (3)	C29—C23—C24—C25	174.8 (3)
C7—C8—C9—C15	−179.6 (3)	C22—C23—C24—C30	178.7 (3)
C14—C8—C9—C15	0.7 (5)	C29—C23—C24—C30	−3.8 (5)
C8—C9—C10—C11	0.4 (6)	C23—C24—C25—C26	0.8 (6)
C15—C9—C10—C11	−179.9 (4)	C30—C24—C25—C26	179.5 (4)
C9—C10—C11—C12	−1.4 (6)	C24—C25—C26—C27	1.1 (6)
C10—C11—C12—C7	1.8 (6)	C25—C26—C27—C22	−1.1 (6)
C8—C7—C12—C11	−1.4 (5)	C23—C22—C27—C26	−0.8 (5)
N1—C7—C12—C11	179.5 (3)	N2—C22—C27—C26	−178.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.85 (2)	2.15 (2)	2.971 (4)	162 (4)
N2—H2N···O2	0.85 (2)	2.12 (2)	2.954 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.85 (2)	2.15 (2)	2.971 (4)	162 (4)
N2—H2N⋯O2	0.85 (2)	2.12 (2)	2.954 (4)	166 (4)