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

The asymmetric unit of the title compound, C(15)H(10)BrNO(4)S, contains two different conformers in which the benzisothia-zole rings are essentially planar, with r.m.s. deviations of 0.012 and 0.017 Å. The mean planes of the benzene rings form dihedral angles 70.49 (13) and 72.79 (11)° with the benzisothia-zole rings. The orientation of the Br atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two mol-ecules. The crystal structure is stabilized by π-π inter-actions between the benzene rings of the benzisothia-zole moieties of one mol-ecule and bromo-benzene rings of the other mol-ecule, with distances between the ring centroids of 3.599 (3) and 3.620 (3) Å, respectively. The crystal packing is further consolidated by pairs of weak inter-molecular C-H⋯O hydrogen bonds, which form inversion dimers.

Related literature

For non-steroidal anti-inflammatory drugs (NSAIDs) and related compounds, see: Lombardino et al. (1971 ▶); Soler (1985 ▶); Carty et al. (1993 ▶); Turck et al. (1995 ▶); Blackham & Owen (1975 ▶); Singh et al. (2007 ▶); Vaccarino et al. (2007 ▶); Kapui et al. (2003 ▶). For related structures, see: Maliha et al. (2007 ▶); Siddiqui et al. (2007 ▶).

Experimental

Crystal data

C15H10BrNO4S

M = 380.21

Triclinic,

a = 7.574 (2) Å

b = 13.903 (4) Å

c = 14.814 (4) Å

α = 110.574 (15)°

β = 96.936 (13)°

γ = 93.640 (14)°

V = 1440.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.02 mm−1

T = 123 K

0.18 × 0.18 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.613, T max = 0.644

12284 measured reflections

6541 independent reflections

5268 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.105

S = 1.12

6541 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −1.04 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/S1600536812022428/pk2412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022428/pk2412Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022428/pk2412Isup3.cml

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

C15H10BrNO4S	Z = 4
Mr = 380.21	F(000) = 760
Triclinic, P1	Dx = 1.753 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.574 (2) Å	Cell parameters from 6425 reflections
b = 13.903 (4) Å	θ = 1.0–27.5°
c = 14.814 (4) Å	µ = 3.02 mm−1
α = 110.574 (15)°	T = 123 K
β = 96.936 (13)°	Prism, colorless
γ = 93.640 (14)°	0.18 × 0.18 × 0.16 mm
V = 1440.3 (7) Å3

Nonius KappaCCD diffractometer	6541 independent reflections
Radiation source: fine-focus sealed tube	5268 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω and φ scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.613, Tmax = 0.644	k = −18→18
12284 measured reflections	l = −19→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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F2) = 0.105	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + 5.440P] where P = (Fo2 + 2Fc2)/3
6541 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −1.04 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
Br1	0.36505 (6)	0.45967 (4)	0.15933 (3)	0.03241 (12)
Br2	0.91717 (7)	0.09057 (4)	0.66368 (3)	0.03844 (13)
S1	0.67803 (14)	0.13040 (8)	−0.09125 (7)	0.0234 (2)
S2	0.60738 (13)	0.34637 (7)	0.39090 (7)	0.02000 (19)
O1	0.8217 (4)	0.1917 (2)	−0.1062 (2)	0.0349 (7)
O2	0.5086 (4)	0.1188 (2)	−0.1509 (2)	0.0321 (7)
O3	0.6920 (4)	0.1327 (2)	0.1629 (2)	0.0283 (6)
O4	0.9038 (4)	0.3378 (2)	0.1237 (2)	0.0310 (7)
O5	0.5563 (4)	0.3780 (2)	0.4859 (2)	0.0283 (6)
O6	0.4665 (4)	0.3119 (2)	0.3092 (2)	0.0283 (6)
O7	1.0338 (4)	0.2269 (2)	0.3508 (2)	0.0260 (6)
O8	0.8207 (5)	0.2096 (2)	0.5384 (2)	0.0389 (8)
N1	0.6521 (5)	0.1750 (2)	0.0257 (2)	0.0215 (7)
N2	0.7478 (4)	0.2569 (2)	0.3791 (2)	0.0207 (7)
C1	0.7402 (5)	0.0120 (3)	−0.0868 (3)	0.0209 (8)
C2	0.7806 (5)	−0.0711 (3)	−0.1628 (3)	0.0250 (8)
H2	0.7750	−0.0703	−0.2270	0.030*
C3	0.8297 (5)	−0.1558 (3)	−0.1406 (3)	0.0277 (9)
H3	0.8576	−0.2148	−0.1908	0.033*
C4	0.8388 (5)	−0.1557 (3)	−0.0463 (3)	0.0261 (9)
H4	0.8734	−0.2146	−0.0332	0.031*
C5	0.7983 (5)	−0.0711 (3)	0.0290 (3)	0.0230 (8)
H5	0.8054	−0.0711	0.0934	0.028*
C6	0.7473 (5)	0.0133 (3)	0.0077 (3)	0.0208 (8)
C7	0.6977 (5)	0.1109 (3)	0.0771 (3)	0.0198 (8)
C8	0.5961 (5)	0.2769 (3)	0.0709 (3)	0.0213 (8)
H8A	0.5346	0.2778	0.1264	0.026*
H8B	0.5100	0.2916	0.0229	0.026*
C9	0.7555 (5)	0.3606 (3)	0.1071 (3)	0.0205 (8)
C10	0.7307 (5)	0.4707 (3)	0.1184 (3)	0.0215 (8)
C11	0.5795 (5)	0.5213 (3)	0.1368 (3)	0.0234 (8)
C12	0.5781 (6)	0.6246 (3)	0.1462 (3)	0.0305 (9)
H12	0.4728	0.6577	0.1583	0.037*
C13	0.7319 (7)	0.6784 (4)	0.1378 (4)	0.0384 (11)
H13	0.7330	0.7492	0.1453	0.046*
C14	0.8831 (7)	0.6296 (4)	0.1187 (4)	0.0386 (11)
H14	0.9878	0.6663	0.1118	0.046*
C15	0.8825 (6)	0.5280 (3)	0.1095 (3)	0.0290 (9)
H15	0.9880	0.4953	0.0967	0.035*
C16	0.7715 (5)	0.4356 (3)	0.3809 (3)	0.0181 (7)
C17	0.7503 (5)	0.5350 (3)	0.3834 (3)	0.0229 (8)
H17	0.6394	0.5629	0.3918	0.028*
C18	0.8992 (5)	0.5917 (3)	0.3730 (3)	0.0249 (8)
H18	0.8906	0.6597	0.3735	0.030*
C19	1.0615 (5)	0.5497 (3)	0.3619 (3)	0.0232 (8)
H19	1.1622	0.5905	0.3564	0.028*
C20	1.0793 (5)	0.4497 (3)	0.3586 (3)	0.0226 (8)
H20	1.1896	0.4213	0.3501	0.027*
C21	0.9302 (5)	0.3926 (3)	0.3681 (3)	0.0181 (7)
C22	0.9183 (5)	0.2841 (3)	0.3645 (3)	0.0197 (8)
C23	0.6895 (6)	0.1524 (3)	0.3720 (3)	0.0224 (8)
H23A	0.7401	0.1020	0.3186	0.027*
H23B	0.5574	0.1393	0.3561	0.027*
C24	0.7505 (5)	0.1370 (3)	0.4683 (3)	0.0204 (8)
C25	0.7189 (5)	0.0296 (3)	0.4674 (3)	0.0196 (8)
C26	0.7853 (5)	−0.0009 (3)	0.5443 (3)	0.0255 (9)
C27	0.7537 (6)	−0.1035 (4)	0.5369 (4)	0.0343 (11)
H27	0.8041	−0.1240	0.5883	0.041*
C28	0.6490 (7)	−0.1757 (4)	0.4549 (4)	0.0383 (12)
H28	0.6255	−0.2452	0.4508	0.046*
C29	0.5792 (6)	−0.1468 (3)	0.3795 (3)	0.0335 (10)
H29	0.5064	−0.1961	0.3236	0.040*
C30	0.6150 (5)	−0.0461 (3)	0.3851 (3)	0.0243 (8)
H30	0.5682	−0.0275	0.3319	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.0246 (2)	0.0352 (2)	0.0418 (3)	0.01061 (18)	0.01351 (19)	0.0153 (2)
Br2	0.0388 (3)	0.0569 (3)	0.0219 (2)	0.0144 (2)	0.00103 (19)	0.0167 (2)
S1	0.0299 (5)	0.0228 (5)	0.0171 (4)	0.0017 (4)	0.0034 (4)	0.0071 (4)
S2	0.0177 (4)	0.0206 (5)	0.0245 (5)	0.0040 (4)	0.0070 (4)	0.0101 (4)
O1	0.048 (2)	0.0283 (16)	0.0300 (16)	−0.0069 (14)	0.0119 (15)	0.0128 (14)
O2	0.0371 (18)	0.0359 (17)	0.0229 (15)	0.0102 (14)	−0.0017 (13)	0.0111 (13)
O3	0.0403 (18)	0.0268 (15)	0.0198 (14)	0.0082 (13)	0.0104 (13)	0.0084 (12)
O4	0.0248 (16)	0.0288 (16)	0.0371 (17)	0.0087 (13)	0.0015 (13)	0.0092 (14)
O5	0.0278 (16)	0.0325 (16)	0.0313 (16)	0.0069 (13)	0.0172 (13)	0.0151 (13)
O6	0.0202 (14)	0.0290 (16)	0.0341 (16)	0.0009 (12)	0.0004 (12)	0.0111 (13)
O7	0.0233 (15)	0.0285 (15)	0.0328 (16)	0.0122 (12)	0.0074 (12)	0.0166 (13)
O8	0.059 (2)	0.0251 (16)	0.0254 (16)	−0.0119 (15)	−0.0055 (15)	0.0068 (13)
N1	0.0300 (18)	0.0185 (16)	0.0148 (15)	0.0028 (14)	0.0034 (14)	0.0044 (13)
N2	0.0239 (17)	0.0175 (16)	0.0249 (17)	0.0046 (13)	0.0076 (14)	0.0110 (14)
C1	0.0184 (19)	0.0199 (19)	0.0218 (19)	−0.0026 (15)	−0.0003 (15)	0.0061 (16)
C2	0.025 (2)	0.028 (2)	0.0169 (18)	−0.0004 (17)	0.0037 (16)	0.0019 (16)
C3	0.023 (2)	0.021 (2)	0.031 (2)	−0.0006 (16)	0.0070 (17)	−0.0009 (17)
C4	0.0187 (19)	0.022 (2)	0.035 (2)	0.0026 (16)	0.0054 (17)	0.0076 (18)
C5	0.023 (2)	0.0214 (19)	0.027 (2)	0.0023 (16)	0.0058 (16)	0.0105 (17)
C6	0.0180 (19)	0.0217 (19)	0.0202 (18)	−0.0023 (15)	0.0034 (15)	0.0052 (16)
C7	0.0206 (19)	0.0157 (18)	0.0222 (19)	−0.0009 (14)	0.0029 (15)	0.0065 (15)
C8	0.0207 (19)	0.0203 (19)	0.0217 (19)	0.0044 (15)	0.0010 (15)	0.0067 (16)
C9	0.024 (2)	0.0204 (19)	0.0158 (17)	0.0051 (15)	0.0028 (15)	0.0039 (15)
C10	0.022 (2)	0.024 (2)	0.0174 (18)	0.0013 (16)	0.0015 (15)	0.0072 (16)
C11	0.023 (2)	0.027 (2)	0.0204 (19)	0.0049 (16)	0.0032 (16)	0.0079 (16)
C12	0.036 (2)	0.026 (2)	0.028 (2)	0.0116 (19)	0.0030 (19)	0.0074 (18)
C13	0.046 (3)	0.023 (2)	0.045 (3)	0.004 (2)	0.001 (2)	0.012 (2)
C14	0.036 (3)	0.034 (3)	0.047 (3)	−0.008 (2)	0.003 (2)	0.019 (2)
C15	0.023 (2)	0.031 (2)	0.033 (2)	0.0036 (18)	0.0031 (18)	0.0122 (19)
C16	0.0201 (19)	0.0215 (19)	0.0129 (16)	0.0022 (15)	0.0024 (14)	0.0064 (15)
C17	0.024 (2)	0.023 (2)	0.0229 (19)	0.0068 (16)	0.0046 (16)	0.0084 (16)
C18	0.027 (2)	0.022 (2)	0.026 (2)	0.0015 (16)	0.0060 (17)	0.0087 (17)
C19	0.022 (2)	0.024 (2)	0.0216 (19)	−0.0064 (16)	0.0027 (16)	0.0085 (16)
C20	0.0170 (19)	0.029 (2)	0.0229 (19)	0.0040 (16)	0.0035 (15)	0.0101 (17)
C21	0.0193 (18)	0.0208 (18)	0.0149 (17)	0.0044 (15)	0.0045 (14)	0.0066 (15)
C22	0.0201 (19)	0.025 (2)	0.0159 (17)	0.0047 (15)	0.0016 (15)	0.0093 (15)
C23	0.029 (2)	0.0188 (19)	0.0212 (19)	−0.0011 (16)	0.0027 (16)	0.0097 (16)
C24	0.0211 (19)	0.0204 (19)	0.0224 (19)	0.0027 (15)	0.0052 (15)	0.0102 (16)
C25	0.0195 (19)	0.0214 (19)	0.0191 (18)	0.0043 (15)	0.0069 (15)	0.0070 (15)
C26	0.022 (2)	0.035 (2)	0.026 (2)	0.0116 (17)	0.0077 (16)	0.0154 (18)
C27	0.038 (3)	0.042 (3)	0.043 (3)	0.022 (2)	0.021 (2)	0.032 (2)
C28	0.047 (3)	0.026 (2)	0.056 (3)	0.015 (2)	0.033 (3)	0.022 (2)
C29	0.037 (3)	0.025 (2)	0.038 (3)	0.0022 (19)	0.018 (2)	0.007 (2)
C30	0.023 (2)	0.022 (2)	0.027 (2)	0.0052 (16)	0.0077 (17)	0.0073 (17)

Br1—C11	1.908 (4)	C10—C15	1.403 (6)
Br2—C26	1.890 (4)	C11—C12	1.394 (6)
S1—O1	1.426 (3)	C12—C13	1.387 (7)
S1—O2	1.433 (3)	C12—H12	0.9500
S1—N1	1.664 (3)	C13—C14	1.377 (7)
S1—C1	1.762 (4)	C13—H13	0.9500
S2—O5	1.429 (3)	C14—C15	1.370 (6)
S2—O6	1.431 (3)	C14—H14	0.9500
S2—N2	1.664 (3)	C15—H15	0.9500
S2—C16	1.757 (4)	C16—C21	1.380 (5)
O3—C7	1.206 (5)	C16—C17	1.389 (5)
O4—C9	1.206 (5)	C17—C18	1.390 (5)
O7—C22	1.207 (4)	C17—H17	0.9500
O8—C24	1.200 (5)	C18—C19	1.397 (6)
N1—C7	1.395 (5)	C18—H18	0.9500
N1—C8	1.453 (5)	C19—C20	1.390 (5)
N2—C22	1.386 (5)	C19—H19	0.9500
N2—C23	1.455 (5)	C20—C21	1.388 (5)
C1—C2	1.382 (5)	C20—H20	0.9500
C1—C6	1.387 (5)	C21—C22	1.487 (5)
C2—C3	1.390 (6)	C23—C24	1.537 (5)
C2—H2	0.9500	C23—H23A	0.9900
C3—C4	1.389 (6)	C23—H23B	0.9900
C3—H3	0.9500	C24—C25	1.493 (5)
C4—C5	1.389 (6)	C25—C26	1.400 (5)
C4—H4	0.9500	C25—C30	1.405 (6)
C5—C6	1.383 (5)	C26—C27	1.394 (6)
C5—H5	0.9500	C27—C28	1.387 (7)
C6—C7	1.489 (5)	C27—H27	0.9500
C8—C9	1.525 (5)	C28—C29	1.373 (7)
C8—H8A	0.9900	C28—H28	0.9500
C8—H8B	0.9900	C29—C30	1.381 (6)
C9—C10	1.507 (5)	C29—H29	0.9500
C10—C11	1.387 (5)	C30—H30	0.9500
O1—S1—O2	116.92 (19)	C14—C13—C12	120.2 (4)
O1—S1—N1	109.81 (18)	C14—C13—H13	119.9
O2—S1—N1	109.41 (18)	C12—C13—H13	119.9
O1—S1—C1	112.50 (19)	C15—C14—C13	119.9 (4)
O2—S1—C1	112.67 (18)	C15—C14—H14	120.1
N1—S1—C1	92.85 (17)	C13—C14—H14	120.1
O5—S2—O6	117.20 (18)	C14—C15—C10	122.0 (4)
O5—S2—N2	109.94 (17)	C14—C15—H15	119.0
O6—S2—N2	109.76 (18)	C10—C15—H15	119.0
O5—S2—C16	112.41 (18)	C21—C16—C17	123.2 (3)
O6—S2—C16	112.30 (17)	C21—C16—S2	110.1 (3)
N2—S2—C16	92.44 (17)	C17—C16—S2	126.7 (3)
C7—N1—C8	123.3 (3)	C16—C17—C18	116.7 (4)
C7—N1—S1	115.4 (3)	C16—C17—H17	121.7
C8—N1—S1	121.2 (3)	C18—C17—H17	121.7
C22—N2—C23	121.7 (3)	C17—C18—C19	120.7 (4)
C22—N2—S2	115.7 (3)	C17—C18—H18	119.7
C23—N2—S2	122.2 (3)	C19—C18—H18	119.7
C2—C1—C6	123.1 (4)	C20—C19—C18	121.7 (4)
C2—C1—S1	127.2 (3)	C20—C19—H19	119.2
C6—C1—S1	109.6 (3)	C18—C19—H19	119.2
C1—C2—C3	116.5 (4)	C21—C20—C19	117.7 (4)
C1—C2—H2	121.7	C21—C20—H20	121.1
C3—C2—H2	121.7	C19—C20—H20	121.1
C4—C3—C2	121.3 (4)	C16—C21—C20	120.1 (3)
C4—C3—H3	119.4	C16—C21—C22	113.3 (3)
C2—C3—H3	119.4	C20—C21—C22	126.6 (3)
C3—C4—C5	121.1 (4)	O7—C22—N2	124.1 (4)
C3—C4—H4	119.5	O7—C22—C21	127.4 (4)
C5—C4—H4	119.5	N2—C22—C21	108.4 (3)
C6—C5—C4	118.3 (4)	N2—C23—C24	110.8 (3)
C6—C5—H5	120.9	N2—C23—H23A	109.5
C4—C5—H5	120.9	C24—C23—H23A	109.5
C5—C6—C1	119.7 (4)	N2—C23—H23B	109.5
C5—C6—C7	126.8 (4)	C24—C23—H23B	109.5
C1—C6—C7	113.5 (3)	H23A—C23—H23B	108.1
O3—C7—N1	124.0 (4)	O8—C24—C25	124.0 (4)
O3—C7—C6	127.5 (4)	O8—C24—C23	119.6 (3)
N1—C7—C6	108.4 (3)	C25—C24—C23	116.4 (3)
N1—C8—C9	111.4 (3)	C26—C25—C30	117.4 (4)
N1—C8—H8A	109.4	C26—C25—C24	124.0 (4)
C9—C8—H8A	109.4	C30—C25—C24	118.6 (3)
N1—C8—H8B	109.4	C27—C26—C25	120.6 (4)
C9—C8—H8B	109.4	C27—C26—Br2	115.6 (3)
H8A—C8—H8B	108.0	C25—C26—Br2	123.8 (3)
O4—C9—C10	119.6 (4)	C28—C27—C26	120.3 (4)
O4—C9—C8	119.7 (3)	C28—C27—H27	119.9
C10—C9—C8	120.6 (3)	C26—C27—H27	119.9
C11—C10—C15	117.1 (4)	C29—C28—C27	120.0 (4)
C11—C10—C9	128.4 (4)	C29—C28—H28	120.0
C15—C10—C9	114.5 (4)	C27—C28—H28	120.0
C10—C11—C12	121.6 (4)	C28—C29—C30	119.9 (4)
C10—C11—Br1	123.4 (3)	C28—C29—H29	120.0
C12—C11—Br1	114.8 (3)	C30—C29—H29	120.0
C13—C12—C11	119.3 (4)	C29—C30—C25	121.8 (4)
C13—C12—H12	120.4	C29—C30—H30	119.1
C11—C12—H12	120.4	C25—C30—H30	119.1
O1—S1—N1—C7	−111.1 (3)	Br1—C11—C12—C13	175.6 (3)
O2—S1—N1—C7	119.3 (3)	C11—C12—C13—C14	1.1 (7)
C1—S1—N1—C7	4.1 (3)	C12—C13—C14—C15	−1.1 (7)
O1—S1—N1—C8	65.3 (3)	C13—C14—C15—C10	0.4 (7)
O2—S1—N1—C8	−64.3 (3)	C11—C10—C15—C14	0.2 (6)
C1—S1—N1—C8	−179.6 (3)	C9—C10—C15—C14	−179.4 (4)
O5—S2—N2—C22	−116.7 (3)	O5—S2—C16—C21	113.1 (3)
O6—S2—N2—C22	113.0 (3)	O6—S2—C16—C21	−112.2 (3)
C16—S2—N2—C22	−1.8 (3)	N2—S2—C16—C21	0.3 (3)
O5—S2—N2—C23	70.9 (3)	O5—S2—C16—C17	−67.8 (4)
O6—S2—N2—C23	−59.4 (3)	O6—S2—C16—C17	66.9 (4)
C16—S2—N2—C23	−174.2 (3)	N2—S2—C16—C17	179.4 (3)
O1—S1—C1—C2	−69.0 (4)	C21—C16—C17—C18	−0.4 (6)
O2—S1—C1—C2	65.8 (4)	S2—C16—C17—C18	−179.4 (3)
N1—S1—C1—C2	178.2 (4)	C16—C17—C18—C19	−0.8 (6)
O1—S1—C1—C6	109.9 (3)	C17—C18—C19—C20	1.5 (6)
O2—S1—C1—C6	−115.4 (3)	C18—C19—C20—C21	−0.9 (6)
N1—S1—C1—C6	−2.9 (3)	C17—C16—C21—C20	1.0 (6)
C6—C1—C2—C3	0.1 (6)	S2—C16—C21—C20	−179.9 (3)
S1—C1—C2—C3	178.8 (3)	C17—C16—C21—C22	−178.0 (3)
C1—C2—C3—C4	−0.5 (6)	S2—C16—C21—C22	1.1 (4)
C2—C3—C4—C5	0.3 (6)	C19—C20—C21—C16	−0.3 (5)
C3—C4—C5—C6	0.4 (6)	C19—C20—C21—C22	178.6 (4)
C4—C5—C6—C1	−0.8 (6)	C23—N2—C22—O7	−4.5 (6)
C4—C5—C6—C7	179.7 (4)	S2—N2—C22—O7	−176.9 (3)
C2—C1—C6—C5	0.6 (6)	C23—N2—C22—C21	175.0 (3)
S1—C1—C6—C5	−178.3 (3)	S2—N2—C22—C21	2.6 (4)
C2—C1—C6—C7	−179.9 (4)	C16—C21—C22—O7	177.2 (4)
S1—C1—C6—C7	1.3 (4)	C20—C21—C22—O7	−1.7 (6)
C8—N1—C7—O3	1.4 (6)	C16—C21—C22—N2	−2.3 (4)
S1—N1—C7—O3	177.7 (3)	C20—C21—C22—N2	178.8 (4)
C8—N1—C7—C6	179.8 (3)	C22—N2—C23—C24	83.4 (4)
S1—N1—C7—C6	−3.9 (4)	S2—N2—C23—C24	−104.7 (3)
C5—C6—C7—O3	−0.7 (7)	N2—C23—C24—O8	6.4 (5)
C1—C6—C7—O3	179.8 (4)	N2—C23—C24—C25	−172.9 (3)
C5—C6—C7—N1	−179.0 (4)	O8—C24—C25—C26	−7.6 (6)
C1—C6—C7—N1	1.5 (4)	C23—C24—C25—C26	171.7 (4)
C7—N1—C8—C9	90.7 (4)	O8—C24—C25—C30	171.8 (4)
S1—N1—C8—C9	−85.4 (4)	C23—C24—C25—C30	−8.9 (5)
N1—C8—C9—O4	−22.3 (5)	C30—C25—C26—C27	2.2 (6)
N1—C8—C9—C10	155.1 (3)	C24—C25—C26—C27	−178.4 (4)
O4—C9—C10—C11	−155.3 (4)	C30—C25—C26—Br2	−176.7 (3)
C8—C9—C10—C11	27.3 (6)	C24—C25—C26—Br2	2.7 (5)
O4—C9—C10—C15	24.3 (5)	C25—C26—C27—C28	−2.9 (6)
C8—C9—C10—C15	−153.1 (4)	Br2—C26—C27—C28	176.0 (3)
C15—C10—C11—C12	−0.2 (6)	C26—C27—C28—C29	1.4 (6)
C9—C10—C11—C12	179.4 (4)	C27—C28—C29—C30	0.7 (6)
C15—C10—C11—Br1	−176.0 (3)	C28—C29—C30—C25	−1.4 (6)
C9—C10—C11—Br1	3.6 (6)	C26—C25—C30—C29	−0.1 (6)
C10—C11—C12—C13	−0.5 (6)	C24—C25—C30—C29	−179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O7i	0.95	2.56	3.238 (5)	129
C14—H14···O1ii	0.95	2.40	3.305 (5)	159
C17—H17···O5iii	0.95	2.43	3.225 (5)	141
C27—H27···O7iv	0.95	2.29	3.164 (5)	153
C30—H30···O2v	0.95	2.51	3.251 (5)	135
C8—H8A···Br1	0.99	2.82	3.165 (4)	101
C23—H23A···O3	0.99	2.48	3.014 (5)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.95	2.40	3.305 (5)	159
C17—H17⋯O5ii	0.95	2.43	3.225 (5)	141
C27—H27⋯O7iii	0.95	2.29	3.164 (5)	153

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