2-[2-(2-Chloro-phen-yl)-2-oxoeth-yl]-2,3-dihydro-1λ(6),2-benzothia-zole-1,1,3-trione.

The asymmetric unit of the title compound, C(15)H(10)ClNO(4)S, contains two independent conformers wherein the 2-chloro-phenyl group in one is rotated by approximately 180° compared to the other mol-ecule. This affects the S-N-C-C(=O) and N-C-C(=O)-C torsion angles giving vlaues of -87.0 (2) and 158.7 (2)° in one mol-ecule and -104.3 (2) and -173.4 (2)° in the other. The benzisothia-zole ring systems in the two mol-ecules are essentially planar (r.m.s. deviations = 0.017 and 0.010 Å) and form dihedral angles of 73.53 (7) and 73.26 (6)° with the benzene rings. In the crystal, there are weak π-π inter-actions between the benzene rings of the benzisothia-zole groups and symmetry-related chloro-benzene rings with centroid-centroid distances of 3.6178 (13) and 3.6267 (15) Å. In addition, pairs of weak inter-molecular C-H⋯O hydrogen bonds form inversion dimers which are connected by further C-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the bromo-substituted analog of the title compound, see: Sattar et al. (2012 ▶). For related structures, see: Maliha et al. (2007 ▶); Siddiqui et al. (2007 ▶).

Experimental

Crystal data

C15H10ClNO4S

M = 335.75

Triclinic,

a = 7.4933 (2) Å

b = 13.9702 (3) Å

c = 14.5844 (3) Å

α = 109.0462 (14)°

β = 96.5998 (14)°

γ = 93.4671 (11)°

V = 1425.77 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 123 K

0.16 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.934, T max = 0.958

12676 measured reflections

6602 independent reflections

5465 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 1.03

6602 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.46 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036653/lh5517sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036653/lh5517Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036653/lh5517Isup3.cml

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

C15H10ClNO4S	Z = 4
Mr = 335.75	F(000) = 688
Triclinic, P1	Dx = 1.564 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4933 (2) Å	Cell parameters from 6513 reflections
b = 13.9702 (3) Å	θ = 1.0–27.5°
c = 14.5844 (3) Å	µ = 0.43 mm−1
α = 109.0462 (14)°	T = 123 K
β = 96.5998 (14)°	Block, colorless
γ = 93.4671 (11)°	0.16 × 0.14 × 0.10 mm
V = 1425.77 (6) Å3

Nonius KappaCCD diffractometer	6602 independent reflections
Radiation source: fine-focus sealed tube	5465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 27.7°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.934, Tmax = 0.958	k = −18→18
12676 measured reflections	l = −18→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0289P)2 + 1.9353P] where P = (Fo2 + 2Fc2)/3
6602 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.37851 (8)	0.45393 (5)	0.14792 (5)	0.03709 (15)
Cl2	0.91058 (10)	0.08491 (6)	0.65590 (4)	0.04241 (17)
S1	0.67930 (8)	0.13106 (4)	−0.09566 (4)	0.02600 (13)
S2	0.60770 (7)	0.34957 (4)	0.38890 (4)	0.02241 (12)
O1	0.8259 (3)	0.18938 (14)	−0.11376 (13)	0.0381 (4)
O2	0.5083 (2)	0.12158 (13)	−0.15434 (12)	0.0348 (4)
O3	0.6914 (2)	0.13362 (13)	0.16209 (11)	0.0315 (4)
O4	0.9088 (2)	0.33337 (13)	0.11577 (13)	0.0343 (4)
O5	0.5508 (2)	0.37794 (13)	0.48340 (12)	0.0317 (4)
O6	0.4695 (2)	0.31718 (13)	0.30561 (12)	0.0312 (4)
O7	1.0402 (2)	0.23212 (13)	0.35123 (12)	0.0301 (4)
O8	0.8149 (3)	0.21186 (13)	0.54195 (13)	0.0400 (5)
N1	0.6544 (3)	0.17557 (14)	0.02268 (13)	0.0263 (4)
N2	0.7514 (3)	0.26105 (14)	0.37907 (14)	0.0237 (4)
C1	0.7391 (3)	0.01406 (17)	−0.08817 (16)	0.0239 (4)
C2	0.7780 (3)	−0.06900 (18)	−0.16356 (17)	0.0288 (5)
H2	0.7729	−0.0684	−0.2288	0.035*
C3	0.8247 (3)	−0.15304 (18)	−0.13889 (18)	0.0306 (5)
H3	0.8507	−0.2119	−0.1886	0.037*
C4	0.8343 (3)	−0.15291 (18)	−0.04349 (18)	0.0297 (5)
H4	0.8678	−0.2114	−0.0289	0.036*
C5	0.7956 (3)	−0.06863 (17)	0.03141 (17)	0.0266 (5)
H5	0.8029	−0.0686	0.0969	0.032*
C6	0.7463 (3)	0.01491 (16)	0.00760 (15)	0.0219 (4)
C7	0.6976 (3)	0.11188 (16)	0.07564 (16)	0.0233 (4)
C8	0.5978 (3)	0.27629 (16)	0.06608 (16)	0.0249 (5)
H8A	0.5333	0.2771	0.1219	0.030*
H8B	0.5128	0.2918	0.0169	0.030*
C9	0.7584 (3)	0.35782 (17)	0.10189 (15)	0.0240 (4)
C10	0.7338 (3)	0.46790 (17)	0.11690 (15)	0.0231 (4)
C11	0.5777 (3)	0.51623 (18)	0.13554 (16)	0.0261 (5)
C12	0.5772 (4)	0.61965 (19)	0.15012 (18)	0.0348 (6)
H12	0.4701	0.6516	0.1631	0.042*
C13	0.7312 (4)	0.6758 (2)	0.1458 (2)	0.0410 (6)
H13	0.7303	0.7465	0.1561	0.049*
C14	0.8871 (4)	0.6298 (2)	0.1265 (2)	0.0402 (6)
H14	0.9931	0.6684	0.1227	0.048*
C15	0.8875 (3)	0.52734 (19)	0.11265 (18)	0.0321 (5)
H15	0.9955	0.4962	0.0999	0.038*
C16	0.7734 (3)	0.43841 (16)	0.37899 (15)	0.0202 (4)
C17	0.7539 (3)	0.53697 (17)	0.38192 (16)	0.0240 (4)
H17	0.6420	0.5649	0.3902	0.029*
C18	0.9051 (3)	0.59344 (17)	0.37227 (16)	0.0259 (5)
H18	0.8970	0.6616	0.3741	0.031*
C19	1.0687 (3)	0.55175 (17)	0.35987 (16)	0.0266 (5)
H19	1.1703	0.5921	0.3536	0.032*
C20	1.0857 (3)	0.45252 (17)	0.35657 (16)	0.0244 (4)
H20	1.1972	0.4242	0.3478	0.029*
C21	0.9355 (3)	0.39583 (16)	0.36650 (15)	0.0207 (4)
C22	0.9235 (3)	0.28879 (17)	0.36418 (15)	0.0219 (4)
C23	0.6939 (3)	0.15852 (16)	0.37356 (16)	0.0252 (5)
H23A	0.7474	0.1096	0.3208	0.030*
H23B	0.5609	0.1457	0.3567	0.030*
C24	0.7508 (3)	0.14107 (17)	0.47071 (16)	0.0238 (4)
C25	0.7229 (3)	0.03392 (17)	0.46952 (16)	0.0224 (4)
C26	0.7910 (3)	0.00201 (19)	0.54732 (17)	0.0286 (5)
C27	0.7632 (4)	−0.0988 (2)	0.5410 (2)	0.0373 (6)
H27	0.8137	−0.1197	0.5933	0.045*
C28	0.6623 (4)	−0.16928 (19)	0.4590 (2)	0.0395 (7)
H28	0.6417	−0.2381	0.4558	0.047*
C29	0.5912 (4)	−0.14066 (18)	0.3819 (2)	0.0340 (6)
H29	0.5207	−0.1891	0.3258	0.041*
C30	0.6236 (3)	−0.04047 (17)	0.38706 (17)	0.0257 (5)
H30	0.5771	−0.0214	0.3329	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.0276 (3)	0.0352 (3)	0.0512 (4)	0.0092 (2)	0.0128 (3)	0.0148 (3)
Cl2	0.0452 (4)	0.0587 (4)	0.0250 (3)	0.0151 (3)	0.0001 (3)	0.0163 (3)
S1	0.0341 (3)	0.0239 (3)	0.0193 (3)	−0.0003 (2)	0.0034 (2)	0.0071 (2)
S2	0.0216 (3)	0.0217 (3)	0.0266 (3)	0.0037 (2)	0.0076 (2)	0.0101 (2)
O1	0.0518 (12)	0.0333 (10)	0.0296 (9)	−0.0081 (8)	0.0095 (8)	0.0120 (8)
O2	0.0414 (10)	0.0362 (10)	0.0255 (8)	0.0069 (8)	−0.0013 (7)	0.0102 (7)
O3	0.0454 (10)	0.0299 (9)	0.0207 (8)	0.0082 (8)	0.0094 (7)	0.0083 (7)
O4	0.0266 (9)	0.0289 (9)	0.0423 (10)	0.0077 (7)	−0.0005 (7)	0.0059 (8)
O5	0.0330 (9)	0.0327 (9)	0.0346 (9)	0.0068 (7)	0.0168 (7)	0.0138 (7)
O6	0.0233 (8)	0.0318 (9)	0.0373 (9)	0.0018 (7)	0.0012 (7)	0.0113 (7)
O7	0.0281 (9)	0.0317 (9)	0.0375 (9)	0.0125 (7)	0.0092 (7)	0.0182 (7)
O8	0.0580 (12)	0.0272 (9)	0.0288 (9)	−0.0103 (8)	−0.0076 (8)	0.0084 (7)
N1	0.0367 (11)	0.0217 (9)	0.0204 (9)	0.0044 (8)	0.0059 (8)	0.0062 (7)
N2	0.0260 (10)	0.0205 (9)	0.0287 (10)	0.0042 (7)	0.0076 (8)	0.0124 (8)
C1	0.0216 (11)	0.0230 (11)	0.0245 (11)	−0.0026 (8)	0.0027 (8)	0.0057 (9)
C2	0.0274 (12)	0.0285 (12)	0.0238 (11)	−0.0042 (9)	0.0042 (9)	0.0008 (9)
C3	0.0235 (11)	0.0243 (11)	0.0355 (13)	−0.0009 (9)	0.0077 (10)	−0.0019 (10)
C4	0.0242 (11)	0.0235 (11)	0.0397 (13)	0.0003 (9)	0.0070 (10)	0.0081 (10)
C5	0.0257 (11)	0.0253 (11)	0.0299 (12)	0.0016 (9)	0.0078 (9)	0.0095 (9)
C6	0.0206 (10)	0.0204 (10)	0.0233 (10)	−0.0012 (8)	0.0062 (8)	0.0051 (8)
C7	0.0233 (11)	0.0213 (10)	0.0252 (11)	0.0002 (8)	0.0047 (8)	0.0078 (9)
C8	0.0280 (12)	0.0216 (11)	0.0247 (11)	0.0036 (9)	0.0037 (9)	0.0072 (9)
C9	0.0269 (11)	0.0248 (11)	0.0196 (10)	0.0048 (9)	0.0033 (8)	0.0060 (9)
C10	0.0261 (11)	0.0243 (11)	0.0187 (10)	0.0036 (9)	0.0024 (8)	0.0070 (8)
C11	0.0270 (12)	0.0285 (12)	0.0225 (11)	0.0057 (9)	0.0018 (9)	0.0084 (9)
C12	0.0416 (15)	0.0287 (12)	0.0343 (13)	0.0128 (11)	0.0015 (11)	0.0107 (10)
C13	0.0545 (18)	0.0247 (12)	0.0429 (15)	0.0028 (12)	0.0007 (13)	0.0125 (11)
C14	0.0447 (16)	0.0324 (14)	0.0445 (15)	−0.0070 (12)	0.0035 (12)	0.0169 (12)
C15	0.0320 (13)	0.0318 (13)	0.0328 (13)	0.0007 (10)	0.0050 (10)	0.0117 (10)
C16	0.0205 (10)	0.0233 (10)	0.0191 (10)	0.0022 (8)	0.0049 (8)	0.0098 (8)
C17	0.0258 (11)	0.0237 (11)	0.0247 (11)	0.0060 (9)	0.0072 (9)	0.0091 (9)
C18	0.0341 (12)	0.0189 (10)	0.0241 (11)	0.0020 (9)	0.0051 (9)	0.0064 (9)
C19	0.0282 (12)	0.0257 (11)	0.0263 (11)	−0.0035 (9)	0.0047 (9)	0.0100 (9)
C20	0.0186 (10)	0.0296 (12)	0.0263 (11)	0.0035 (9)	0.0036 (8)	0.0108 (9)
C21	0.0219 (10)	0.0235 (10)	0.0177 (10)	0.0040 (8)	0.0032 (8)	0.0077 (8)
C22	0.0227 (11)	0.0259 (11)	0.0201 (10)	0.0053 (9)	0.0040 (8)	0.0109 (8)
C23	0.0317 (12)	0.0206 (10)	0.0249 (11)	0.0020 (9)	0.0049 (9)	0.0096 (9)
C24	0.0246 (11)	0.0246 (11)	0.0235 (11)	−0.0003 (9)	0.0047 (9)	0.0098 (9)
C25	0.0218 (11)	0.0257 (11)	0.0244 (11)	0.0055 (9)	0.0088 (8)	0.0122 (9)
C26	0.0290 (12)	0.0369 (13)	0.0273 (11)	0.0141 (10)	0.0126 (9)	0.0161 (10)
C27	0.0433 (15)	0.0456 (15)	0.0419 (14)	0.0260 (13)	0.0238 (12)	0.0306 (13)
C28	0.0507 (17)	0.0251 (12)	0.0568 (17)	0.0160 (12)	0.0338 (14)	0.0217 (12)
C29	0.0364 (14)	0.0215 (11)	0.0448 (15)	0.0034 (10)	0.0185 (11)	0.0078 (10)
C30	0.0288 (12)	0.0232 (11)	0.0267 (11)	0.0034 (9)	0.0071 (9)	0.0092 (9)

Cl1—C11	1.739 (2)	C10—C15	1.398 (3)
Cl2—C26	1.733 (3)	C11—C12	1.390 (3)
S1—O1	1.4277 (18)	C12—C13	1.375 (4)
S1—O2	1.4300 (18)	C12—H12	0.9500
S1—N1	1.6697 (19)	C13—C14	1.380 (4)
S1—C1	1.754 (2)	C13—H13	0.9500
S2—O5	1.4273 (17)	C14—C15	1.379 (4)
S2—O6	1.4310 (17)	C14—H14	0.9500
S2—N2	1.6700 (19)	C15—H15	0.9500
S2—C16	1.754 (2)	C16—C17	1.381 (3)
O3—C7	1.204 (3)	C16—C21	1.389 (3)
O4—C9	1.211 (3)	C17—C18	1.388 (3)
O7—C22	1.205 (3)	C17—H17	0.9500
O8—C24	1.202 (3)	C18—C19	1.394 (3)
N1—C7	1.385 (3)	C18—H18	0.9500
N1—C8	1.454 (3)	C19—C20	1.385 (3)
N2—C22	1.385 (3)	C19—H19	0.9500
N2—C23	1.444 (3)	C20—C21	1.386 (3)
C1—C2	1.386 (3)	C20—H20	0.9500
C1—C6	1.388 (3)	C21—C22	1.482 (3)
C2—C3	1.388 (4)	C23—C24	1.532 (3)
C2—H2	0.9500	C23—H23A	0.9900
C3—C4	1.384 (4)	C23—H23B	0.9900
C3—H3	0.9500	C24—C25	1.493 (3)
C4—C5	1.392 (3)	C25—C30	1.402 (3)
C4—H4	0.9500	C25—C26	1.404 (3)
C5—C6	1.381 (3)	C26—C27	1.383 (4)
C5—H5	0.9500	C27—C28	1.380 (4)
C6—C7	1.490 (3)	C27—H27	0.9500
C8—C9	1.523 (3)	C28—C29	1.374 (4)
C8—H8A	0.9900	C28—H28	0.9500
C8—H8B	0.9900	C29—C30	1.382 (3)
C9—C10	1.507 (3)	C29—H29	0.9500
C10—C11	1.396 (3)	C30—H30	0.9500
O1—S1—O2	117.15 (11)	C12—C13—C14	120.2 (2)
O1—S1—N1	109.99 (10)	C12—C13—H13	119.9
O2—S1—N1	109.32 (10)	C14—C13—H13	119.9
O1—S1—C1	112.33 (11)	C15—C14—C13	119.4 (3)
O2—S1—C1	112.65 (11)	C15—C14—H14	120.3
N1—S1—C1	92.64 (10)	C13—C14—H14	120.3
O5—S2—O6	117.21 (11)	C14—C15—C10	121.9 (2)
O5—S2—N2	109.79 (10)	C14—C15—H15	119.0
O6—S2—N2	109.74 (10)	C10—C15—H15	119.0
O5—S2—C16	112.99 (10)	C17—C16—C21	122.5 (2)
O6—S2—C16	111.84 (10)	C17—C16—S2	127.32 (17)
N2—S2—C16	92.49 (10)	C21—C16—S2	110.21 (16)
C7—N1—C8	123.36 (18)	C16—C17—C18	117.0 (2)
C7—N1—S1	115.46 (15)	C16—C17—H17	121.5
C8—N1—S1	121.14 (15)	C18—C17—H17	121.5
C22—N2—C23	122.02 (18)	C17—C18—C19	121.1 (2)
C22—N2—S2	115.33 (14)	C17—C18—H18	119.5
C23—N2—S2	122.17 (16)	C19—C18—H18	119.5
C2—C1—C6	122.6 (2)	C20—C19—C18	121.1 (2)
C2—C1—S1	127.34 (18)	C20—C19—H19	119.4
C6—C1—S1	110.04 (16)	C18—C19—H19	119.4
C1—C2—C3	116.6 (2)	C19—C20—C21	118.1 (2)
C1—C2—H2	121.7	C19—C20—H20	121.0
C3—C2—H2	121.7	C21—C20—H20	121.0
C4—C3—C2	121.4 (2)	C20—C21—C16	120.2 (2)
C4—C3—H3	119.3	C20—C21—C22	126.94 (19)
C2—C3—H3	119.3	C16—C21—C22	112.88 (19)
C3—C4—C5	121.2 (2)	O7—C22—N2	123.5 (2)
C3—C4—H4	119.4	O7—C22—C21	127.5 (2)
C5—C4—H4	119.4	N2—C22—C21	109.01 (18)
C6—C5—C4	117.9 (2)	N2—C23—C24	111.54 (18)
C6—C5—H5	121.0	N2—C23—H23A	109.3
C4—C5—H5	121.0	C24—C23—H23A	109.3
C5—C6—C1	120.2 (2)	N2—C23—H23B	109.3
C5—C6—C7	126.7 (2)	C24—C23—H23B	109.3
C1—C6—C7	113.05 (19)	H23A—C23—H23B	108.0
O3—C7—N1	123.8 (2)	O8—C24—C25	124.0 (2)
O3—C7—C6	127.5 (2)	O8—C24—C23	119.7 (2)
N1—C7—C6	108.69 (18)	C25—C24—C23	116.26 (18)
N1—C8—C9	111.51 (18)	C30—C25—C26	116.9 (2)
N1—C8—H8A	109.3	C30—C25—C24	119.42 (19)
C9—C8—H8A	109.3	C26—C25—C24	123.6 (2)
N1—C8—H8B	109.3	C27—C26—C25	120.8 (2)
C9—C8—H8B	109.3	C27—C26—Cl2	116.34 (19)
H8A—C8—H8B	108.0	C25—C26—Cl2	122.81 (19)
O4—C9—C10	119.5 (2)	C28—C27—C26	120.3 (2)
O4—C9—C8	119.5 (2)	C28—C27—H27	119.9
C10—C9—C8	121.01 (19)	C26—C27—H27	119.9
C11—C10—C15	117.4 (2)	C29—C28—C27	120.6 (2)
C11—C10—C9	127.5 (2)	C29—C28—H28	119.7
C15—C10—C9	115.1 (2)	C27—C28—H28	119.7
C12—C11—C10	120.8 (2)	C28—C29—C30	119.1 (2)
C12—C11—Cl1	116.29 (19)	C28—C29—H29	120.4
C10—C11—Cl1	122.82 (18)	C30—C29—H29	120.4
C13—C12—C11	120.2 (2)	C29—C30—C25	122.2 (2)
C13—C12—H12	119.9	C29—C30—H30	118.9
C11—C12—H12	119.9	C25—C30—H30	118.9
O1—S1—N1—C7	−111.31 (18)	Cl1—C11—C12—C13	177.3 (2)
O2—S1—N1—C7	118.75 (18)	C11—C12—C13—C14	0.3 (4)
C1—S1—N1—C7	3.62 (18)	C12—C13—C14—C15	−0.7 (4)
O1—S1—N1—C8	66.4 (2)	C13—C14—C15—C10	0.5 (4)
O2—S1—N1—C8	−63.5 (2)	C11—C10—C15—C14	0.2 (3)
C1—S1—N1—C8	−178.64 (18)	C9—C10—C15—C14	−179.0 (2)
O5—S2—N2—C22	−118.06 (16)	O5—S2—C16—C17	−66.6 (2)
O6—S2—N2—C22	111.76 (17)	O6—S2—C16—C17	68.2 (2)
C16—S2—N2—C22	−2.52 (17)	N2—S2—C16—C17	−179.3 (2)
O5—S2—N2—C23	69.74 (19)	O5—S2—C16—C21	113.82 (16)
O6—S2—N2—C23	−60.45 (19)	O6—S2—C16—C21	−111.35 (16)
C16—S2—N2—C23	−174.73 (17)	N2—S2—C16—C21	1.08 (16)
O1—S1—C1—C2	−68.9 (2)	C21—C16—C17—C18	−0.3 (3)
O2—S1—C1—C2	66.0 (2)	S2—C16—C17—C18	−179.87 (17)
N1—S1—C1—C2	178.2 (2)	C16—C17—C18—C19	0.2 (3)
O1—S1—C1—C6	110.06 (17)	C17—C18—C19—C20	0.1 (3)
O2—S1—C1—C6	−115.04 (17)	C18—C19—C20—C21	−0.3 (3)
N1—S1—C1—C6	−2.83 (17)	C19—C20—C21—C16	0.2 (3)
C6—C1—C2—C3	0.2 (3)	C19—C20—C21—C22	179.4 (2)
S1—C1—C2—C3	179.07 (18)	C17—C16—C21—C20	0.1 (3)
C1—C2—C3—C4	−0.9 (3)	S2—C16—C21—C20	179.73 (16)
C2—C3—C4—C5	0.6 (4)	C17—C16—C21—C22	−179.13 (19)
C3—C4—C5—C6	0.3 (3)	S2—C16—C21—C22	0.5 (2)
C4—C5—C6—C1	−1.0 (3)	C23—N2—C22—O7	−4.3 (3)
C4—C5—C6—C7	179.3 (2)	S2—N2—C22—O7	−176.55 (18)
C2—C1—C6—C5	0.8 (3)	C23—N2—C22—C21	175.33 (18)
S1—C1—C6—C5	−178.28 (17)	S2—N2—C22—C21	3.1 (2)
C2—C1—C6—C7	−179.5 (2)	C20—C21—C22—O7	−1.8 (4)
S1—C1—C6—C7	1.5 (2)	C16—C21—C22—O7	177.4 (2)
C8—N1—C7—O3	0.4 (4)	C20—C21—C22—N2	178.6 (2)
S1—N1—C7—O3	178.06 (19)	C16—C21—C22—N2	−2.2 (2)
C8—N1—C7—C6	179.05 (19)	C22—N2—C23—C24	84.0 (2)
S1—N1—C7—C6	−3.3 (2)	S2—N2—C23—C24	−104.3 (2)
C5—C6—C7—O3	−0.7 (4)	N2—C23—C24—O8	8.2 (3)
C1—C6—C7—O3	179.6 (2)	N2—C23—C24—C25	−171.35 (18)
C5—C6—C7—N1	−179.3 (2)	O8—C24—C25—C30	170.8 (2)
C1—C6—C7—N1	1.0 (3)	C23—C24—C25—C30	−9.7 (3)
C7—N1—C8—C9	90.5 (3)	O8—C24—C25—C26	−9.2 (4)
S1—N1—C8—C9	−87.0 (2)	C23—C24—C25—C26	170.3 (2)
N1—C8—C9—O4	−19.1 (3)	C30—C25—C26—C27	1.2 (3)
N1—C8—C9—C10	158.73 (19)	C24—C25—C26—C27	−178.8 (2)
O4—C9—C10—C11	−157.7 (2)	C30—C25—C26—Cl2	−178.03 (17)
C8—C9—C10—C11	24.5 (3)	C24—C25—C26—Cl2	2.0 (3)
O4—C9—C10—C15	21.4 (3)	C25—C26—C27—C28	−2.2 (4)
C8—C9—C10—C15	−156.5 (2)	Cl2—C26—C27—C28	177.04 (19)
C15—C10—C11—C12	−0.6 (3)	C26—C27—C28—C29	1.3 (4)
C9—C10—C11—C12	178.5 (2)	C27—C28—C29—C30	0.7 (4)
C15—C10—C11—Cl1	−177.34 (17)	C28—C29—C30—C25	−1.7 (4)
C9—C10—C11—Cl1	1.7 (3)	C26—C25—C30—C29	0.8 (3)
C10—C11—C12—C13	0.4 (4)	C24—C25—C30—C29	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O7i	0.95	2.53	3.234 (3)	131
C14—H14···O1ii	0.95	2.39	3.284 (3)	158
C17—H17···O5iii	0.95	2.43	3.213 (3)	139
C27—H27···O7iv	0.95	2.27	3.133 (3)	151
C30—H30···O2v	0.95	2.51	3.219 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O7i	0.95	2.53	3.234 (3)	131
C14—H14⋯O1ii	0.95	2.39	3.284 (3)	158
C17—H17⋯O5iii	0.95	2.43	3.213 (3)	139
C27—H27⋯O7iv	0.95	2.27	3.133 (3)	151
C30—H30⋯O2v	0.95	2.51	3.219 (3)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .