5,17-Dibromo-26,28-dihy-droxy-25,27-diprop-oxy-2,8,14,20-tetra-thia-calix[4]arene.

In the title compound, C(30)H(26)Br(2)O(4)S(4), the thia-calix[4]arene unit adopts a pinched cone conformation, with one of the ether-substituted rings bent towards the calix cavity and the two phenolic rings bent outwards. The phenyl rings make dihedral angles of 27.12 (9), 36.71 (10), 75.04 (8), and 76.01 (7)° with the virtual plane defined by the four bridging S atoms. The two opposite ether-substituted rings are almost parallel to each other, with an inter-planar anagle of 2.99 (12)°, while the two phenolic rings are nearly perpendicular to each other, making a dihedral angle of 74.52 (11)° and a Br⋯Br distance of 13.17 (2) Å. Two intra-molecular O-H⋯O hydrogen bonds between the OH groups and the same ether O atom stabilize the cone conformation. In the crystal, two different chains of mol-ecules, one with alternating and the other with tail-to-tail orientations, are formed by inter-molecular offset-face-to-face π-π stacking inter-actions with distances of 3.606 (3) to 4.488 (4) Å between the centroids of the aromatic rings.

Related literature

For general background to the chemistry of thia­calix[4]arenes, see: Shokova & Kovalev (2003 ▶); Lhoták (2004 ▶); Morohashi et al. (2006 ▶); Kajiwara et al. (2007 ▶); Guo et al. (2007 ▶). For the synthesis and related structures, see: Lhoták et al. (2001 ▶); Kasyan et al. (2003 ▶); Desroches et al. (2004 ▶); Kasyan et al. (2006 ▶); Morohashi et al. (2006 ▶); Xu et al. (2008 ▶); Chen et al. (2010 ▶). For π–π stacking inter­actions, see: Tsuzuki et al. (2002 ▶).

Experimental

Crystal data

C30H26Br2O4S4

M = 738.57

Triclinic,

a = 9.3788 (16) Å

b = 11.712 (2) Å

c = 14.768 (3) Å

α = 97.904 (2)°

β = 95.614 (1)°

γ = 107.738 (2)°

V = 1513.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.99 mm−1

T = 298 K

0.29 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.478, T max = 0.586

7993 measured reflections

5513 independent reflections

4162 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.05

5513 reflections

365 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S1600536811013043/im2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013043/im2275Isup2.hkl

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

C30H26Br2O4S4	Z = 2
Mr = 738.57	F(000) = 744
Triclinic, P1	Dx = 1.621 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3788 (16) Å	Cell parameters from 2882 reflections
b = 11.712 (2) Å	θ = 2.5–26.7°
c = 14.768 (3) Å	µ = 2.99 mm−1
α = 97.904 (2)°	T = 298 K
β = 95.614 (1)°	Block, colourless
γ = 107.738 (2)°	0.29 × 0.21 × 0.20 mm
V = 1513.5 (4) Å3

Bruker SMART CCD area-detector diffractometer	5513 independent reflections
Radiation source: fine-focus sealed tube	4162 reflections with I > 2σ(I)
graphite	Rint = 0.017
phi and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→11
Tmin = 0.478, Tmax = 0.586	k = −12→14
7993 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.5589P] where P = (Fo2 + 2Fc2)/3
5513 reflections	(Δ/σ)max = 0.001
365 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.54 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	0.51306 (5)	0.32748 (4)	1.28607 (3)	0.06261 (15)
Br2	−0.19390 (6)	−0.37147 (4)	0.49367 (3)	0.07472 (17)
C1	−0.1371 (4)	0.0988 (3)	0.7904 (2)	0.0413 (8)
C2	−0.2029 (4)	0.0044 (3)	0.8354 (3)	0.0525 (9)
H2	−0.2691	−0.0686	0.8016	0.063*
C3	−0.1711 (5)	0.0178 (4)	0.9301 (3)	0.0570 (10)
H3	−0.2138	−0.0469	0.9596	0.068*
C4	−0.0766 (4)	0.1264 (4)	0.9810 (3)	0.0526 (10)
H4	−0.0574	0.1352	1.0450	0.063*
C5	−0.0097 (4)	0.2227 (3)	0.9378 (2)	0.0434 (8)
C6	−0.0376 (4)	0.2078 (3)	0.8419 (2)	0.0387 (8)
C7	0.2766 (4)	0.3469 (3)	1.0398 (2)	0.0414 (8)
C8	0.3184 (4)	0.3436 (3)	1.1317 (2)	0.0451 (9)
H8	0.2522	0.3474	1.1741	0.054*
C9	0.4581 (4)	0.3349 (3)	1.1600 (2)	0.0440 (8)
C10	0.5564 (4)	0.3273 (3)	1.0981 (2)	0.0449 (8)
H10	0.6499	0.3201	1.1181	0.054*
C11	0.5164 (4)	0.3305 (3)	1.0062 (2)	0.0412 (8)
C12	0.3760 (4)	0.3422 (3)	0.9761 (2)	0.0408 (8)
C13	0.5253 (4)	0.1679 (3)	0.8624 (2)	0.0367 (7)
C14	0.4575 (4)	0.0772 (3)	0.9097 (2)	0.0439 (8)
H14	0.4753	0.0914	0.9739	0.053*
C15	0.3638 (4)	−0.0341 (3)	0.8626 (3)	0.0505 (9)
H15	0.3194	−0.0953	0.8948	0.061*
C16	0.3362 (4)	−0.0543 (3)	0.7679 (2)	0.0453 (8)
H16	0.2729	−0.1297	0.7361	0.054*
C17	0.4008 (4)	0.0357 (3)	0.7190 (2)	0.0357 (7)
C18	0.5011 (4)	0.1471 (3)	0.7661 (2)	0.0344 (7)
C19	0.1502 (4)	−0.0465 (3)	0.5925 (2)	0.0387 (8)
C20	0.0703 (4)	−0.1655 (3)	0.5527 (2)	0.0443 (8)
H20	0.1209	−0.2168	0.5282	0.053*
C21	−0.0847 (4)	−0.2084 (3)	0.5492 (2)	0.0467 (9)
C22	−0.1623 (4)	−0.1353 (3)	0.5865 (2)	0.0465 (9)
H22	−0.2667	−0.1656	0.5841	0.056*
C23	−0.0828 (4)	−0.0161 (3)	0.6278 (2)	0.0399 (8)
C24	0.0744 (4)	0.0297 (3)	0.6307 (2)	0.0401 (8)
C25	−0.0263 (4)	0.3907 (3)	0.7817 (3)	0.0548 (10)
H25A	−0.1217	0.3545	0.7407	0.066*
H25B	−0.0457	0.4288	0.8398	0.066*
C26	0.0777 (6)	0.4811 (4)	0.7405 (4)	0.0778 (14)
H26A	0.0879	0.4421	0.6803	0.093*
H26B	0.1763	0.5068	0.7784	0.093*
C27	0.0364 (6)	0.5914 (4)	0.7288 (4)	0.0860 (16)
H27A	−0.0710	0.5689	0.7107	0.129*
H27B	0.0877	0.6287	0.6819	0.129*
H27C	0.0658	0.6480	0.7861	0.129*
C28	0.5073 (4)	0.3165 (3)	0.6889 (3)	0.0496 (9)
H28A	0.4971	0.3710	0.7417	0.059*
H28B	0.4071	0.2716	0.6553	0.059*
C29	0.6031 (4)	0.3874 (3)	0.6276 (3)	0.0506 (9)
H29A	0.7014	0.4335	0.6632	0.061*
H29B	0.5568	0.4453	0.6080	0.061*
C30	0.6257 (6)	0.3113 (4)	0.5436 (3)	0.0728 (13)
H30A	0.6726	0.2542	0.5621	0.109*
H30B	0.6895	0.3629	0.5083	0.109*
H30C	0.5295	0.2679	0.5063	0.109*
O1	0.5815 (3)	0.2325 (2)	0.71942 (15)	0.0412 (5)
O2	0.3429 (3)	0.3459 (2)	0.88626 (15)	0.0491 (6)
H2A	0.2598	0.3551	0.8768	0.074*
O3	0.0416 (2)	0.2975 (2)	0.79765 (16)	0.0423 (5)
O4	0.1557 (3)	0.1454 (2)	0.66895 (17)	0.0474 (6)
H4A	0.0986	0.1822	0.6857	0.071*
S4	0.64004 (10)	0.31392 (8)	0.92504 (6)	0.0459 (2)
S3	0.35097 (10)	0.00864 (8)	0.59664 (6)	0.0453 (2)
S2	−0.18282 (10)	0.08270 (9)	0.66809 (6)	0.0486 (2)
S1	0.10033 (11)	0.36788 (9)	1.00496 (7)	0.0512 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.0684 (3)	0.0745 (3)	0.0419 (2)	0.0225 (2)	0.00312 (19)	0.00470 (19)
Br2	0.0791 (3)	0.0426 (2)	0.0834 (3)	0.0006 (2)	0.0035 (3)	−0.0026 (2)
C1	0.0335 (18)	0.048 (2)	0.0477 (19)	0.0186 (16)	0.0124 (15)	0.0088 (16)
C2	0.045 (2)	0.047 (2)	0.068 (3)	0.0160 (18)	0.0165 (19)	0.0109 (19)
C3	0.057 (3)	0.059 (3)	0.068 (3)	0.024 (2)	0.024 (2)	0.030 (2)
C4	0.053 (2)	0.068 (3)	0.049 (2)	0.030 (2)	0.0175 (19)	0.019 (2)
C5	0.0358 (19)	0.052 (2)	0.049 (2)	0.0241 (17)	0.0109 (16)	0.0067 (17)
C6	0.0328 (18)	0.0460 (19)	0.0454 (19)	0.0214 (16)	0.0119 (15)	0.0108 (16)
C7	0.0396 (19)	0.0395 (19)	0.045 (2)	0.0158 (16)	0.0072 (16)	−0.0006 (15)
C8	0.048 (2)	0.045 (2)	0.0416 (19)	0.0154 (17)	0.0140 (17)	0.0007 (15)
C9	0.048 (2)	0.0415 (19)	0.0390 (18)	0.0144 (17)	0.0035 (16)	−0.0005 (15)
C10	0.042 (2)	0.044 (2)	0.046 (2)	0.0143 (17)	0.0018 (16)	−0.0012 (16)
C11	0.0351 (19)	0.0409 (19)	0.0448 (19)	0.0112 (15)	0.0085 (15)	−0.0008 (15)
C12	0.042 (2)	0.0375 (18)	0.0420 (19)	0.0143 (15)	0.0063 (16)	0.0016 (15)
C13	0.0290 (17)	0.0390 (18)	0.0446 (19)	0.0153 (14)	0.0079 (14)	0.0042 (15)
C14	0.048 (2)	0.049 (2)	0.0393 (18)	0.0201 (18)	0.0081 (16)	0.0118 (16)
C15	0.061 (3)	0.041 (2)	0.054 (2)	0.0167 (19)	0.0138 (19)	0.0193 (17)
C16	0.047 (2)	0.0356 (18)	0.053 (2)	0.0128 (16)	0.0079 (17)	0.0065 (16)
C17	0.0349 (18)	0.0389 (18)	0.0384 (17)	0.0178 (15)	0.0094 (14)	0.0076 (14)
C18	0.0294 (17)	0.0378 (17)	0.0409 (18)	0.0155 (14)	0.0107 (14)	0.0088 (14)
C19	0.0409 (19)	0.0436 (19)	0.0302 (16)	0.0117 (16)	0.0070 (14)	0.0051 (14)
C20	0.054 (2)	0.046 (2)	0.0348 (18)	0.0190 (18)	0.0084 (16)	0.0064 (15)
C21	0.053 (2)	0.0346 (18)	0.0427 (19)	0.0037 (17)	−0.0003 (17)	0.0039 (15)
C22	0.040 (2)	0.047 (2)	0.047 (2)	0.0054 (17)	0.0043 (16)	0.0118 (17)
C23	0.0362 (19)	0.046 (2)	0.0383 (18)	0.0118 (16)	0.0075 (15)	0.0103 (15)
C24	0.040 (2)	0.0428 (19)	0.0366 (17)	0.0113 (16)	0.0056 (15)	0.0076 (15)
C25	0.041 (2)	0.054 (2)	0.076 (3)	0.0204 (18)	0.0100 (19)	0.023 (2)
C26	0.071 (3)	0.060 (3)	0.111 (4)	0.017 (2)	0.034 (3)	0.037 (3)
C27	0.065 (3)	0.067 (3)	0.125 (4)	0.008 (2)	0.005 (3)	0.049 (3)
C28	0.047 (2)	0.048 (2)	0.064 (2)	0.0217 (18)	0.0218 (19)	0.0181 (18)
C29	0.048 (2)	0.045 (2)	0.062 (2)	0.0138 (17)	0.0131 (18)	0.0164 (18)
C30	0.093 (4)	0.072 (3)	0.064 (3)	0.027 (3)	0.038 (3)	0.028 (2)
O1	0.0362 (13)	0.0439 (13)	0.0472 (13)	0.0125 (11)	0.0154 (11)	0.0156 (11)
O2	0.0443 (15)	0.0672 (17)	0.0424 (14)	0.0265 (13)	0.0083 (11)	0.0109 (12)
O3	0.0342 (13)	0.0456 (13)	0.0503 (14)	0.0144 (11)	0.0116 (11)	0.0113 (11)
O4	0.0373 (13)	0.0400 (13)	0.0595 (15)	0.0085 (11)	0.0113 (12)	−0.0035 (11)
S4	0.0334 (5)	0.0504 (5)	0.0491 (5)	0.0100 (4)	0.0085 (4)	−0.0014 (4)
S3	0.0415 (5)	0.0544 (5)	0.0383 (5)	0.0137 (4)	0.0129 (4)	0.0011 (4)
S2	0.0390 (5)	0.0596 (6)	0.0484 (5)	0.0207 (4)	0.0022 (4)	0.0051 (4)
S1	0.0480 (6)	0.0588 (6)	0.0516 (5)	0.0303 (5)	0.0067 (4)	−0.0043 (4)

Br1—C9	1.904 (3)	C17—S3	1.781 (3)
Br2—C21	1.893 (3)	C18—O1	1.369 (4)
C1—C2	1.382 (5)	C19—C20	1.379 (5)
C1—C6	1.395 (5)	C19—C24	1.396 (5)
C1—S2	1.786 (4)	C19—S3	1.787 (3)
C2—C3	1.377 (6)	C20—C21	1.379 (5)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.374 (6)	C21—C22	1.376 (5)
C3—H3	0.9300	C22—C23	1.386 (5)
C4—C5	1.386 (5)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.400 (5)
C5—C6	1.392 (5)	C23—S2	1.776 (3)
C5—S1	1.790 (4)	C24—O4	1.346 (4)
C6—O3	1.375 (4)	C25—C26	1.451 (5)
C7—C8	1.383 (5)	C25—O3	1.456 (4)
C7—C12	1.395 (5)	C25—H25A	0.9700
C7—S1	1.782 (4)	C25—H25B	0.9700
C8—C9	1.374 (5)	C26—C27	1.485 (6)
C8—H8	0.9300	C26—H26A	0.9700
C9—C10	1.373 (5)	C26—H26B	0.9700
C10—C11	1.381 (5)	C27—H27A	0.9600
C10—H10	0.9300	C27—H27B	0.9600
C11—C12	1.401 (5)	C27—H27C	0.9600
C11—S4	1.779 (3)	C28—O1	1.461 (4)
C12—O2	1.343 (4)	C28—C29	1.492 (5)
C13—C14	1.378 (5)	C28—H28A	0.9700
C13—C18	1.394 (4)	C28—H28B	0.9700
C13—S4	1.785 (3)	C29—C30	1.498 (5)
C14—C15	1.373 (5)	C29—H29A	0.9700
C14—H14	0.9300	C29—H29B	0.9700
C15—C16	1.372 (5)	C30—H30A	0.9600
C15—H15	0.9300	C30—H30B	0.9600
C16—C17	1.379 (5)	C30—H30C	0.9600
C16—H16	0.9300	O2—H2A	0.8200
C17—C18	1.395 (4)	O4—H4A	0.8200
C2—C1—C6	119.3 (3)	C21—C20—H20	120.0
C2—C1—S2	120.3 (3)	C19—C20—H20	120.0
C6—C1—S2	120.4 (3)	C22—C21—C20	121.3 (3)
C3—C2—C1	120.5 (4)	C22—C21—Br2	118.9 (3)
C3—C2—H2	119.8	C20—C21—Br2	119.8 (3)
C1—C2—H2	119.8	C21—C22—C23	119.2 (3)
C4—C3—C2	120.2 (4)	C21—C22—H22	120.4
C4—C3—H3	119.9	C23—C22—H22	120.4
C2—C3—H3	119.9	C22—C23—C24	120.4 (3)
C3—C4—C5	120.6 (4)	C22—C23—S2	119.6 (3)
C3—C4—H4	119.7	C24—C23—S2	119.8 (3)
C5—C4—H4	119.7	O4—C24—C19	118.4 (3)
C4—C5—C6	119.2 (3)	O4—C24—C23	122.4 (3)
C4—C5—S1	120.3 (3)	C19—C24—C23	119.2 (3)
C6—C5—S1	120.3 (3)	C26—C25—O3	108.5 (3)
O3—C6—C5	119.6 (3)	C26—C25—H25A	110.0
O3—C6—C1	120.0 (3)	O3—C25—H25A	110.0
C5—C6—C1	120.2 (3)	C26—C25—H25B	110.0
C8—C7—C12	120.3 (3)	O3—C25—H25B	110.0
C8—C7—S1	119.5 (3)	H25A—C25—H25B	108.4
C12—C7—S1	120.1 (3)	C25—C26—C27	116.5 (4)
C9—C8—C7	119.8 (3)	C25—C26—H26A	108.2
C9—C8—H8	120.1	C27—C26—H26A	108.2
C7—C8—H8	120.1	C25—C26—H26B	108.2
C10—C9—C8	121.0 (3)	C27—C26—H26B	108.2
C10—C9—Br1	119.6 (3)	H26A—C26—H26B	107.3
C8—C9—Br1	119.4 (3)	C26—C27—H27A	109.5
C9—C10—C11	120.0 (3)	C26—C27—H27B	109.5
C9—C10—H10	120.0	H27A—C27—H27B	109.5
C11—C10—H10	120.0	C26—C27—H27C	109.5
C10—C11—C12	120.1 (3)	H27A—C27—H27C	109.5
C10—C11—S4	120.0 (3)	H27B—C27—H27C	109.5
C12—C11—S4	119.9 (3)	O1—C28—C29	107.6 (3)
O2—C12—C7	123.3 (3)	O1—C28—H28A	110.2
O2—C12—C11	117.8 (3)	C29—C28—H28A	110.2
C7—C12—C11	118.9 (3)	O1—C28—H28B	110.2
C14—C13—C18	120.3 (3)	C29—C28—H28B	110.2
C14—C13—S4	119.8 (3)	H28A—C28—H28B	108.5
C18—C13—S4	119.9 (2)	C28—C29—C30	114.4 (3)
C15—C14—C13	120.5 (3)	C28—C29—H29A	108.7
C15—C14—H14	119.7	C30—C29—H29A	108.7
C13—C14—H14	119.7	C28—C29—H29B	108.7
C16—C15—C14	119.6 (3)	C30—C29—H29B	108.7
C16—C15—H15	120.2	H29A—C29—H29B	107.6
C14—C15—H15	120.2	C29—C30—H30A	109.5
C15—C16—C17	121.0 (3)	C29—C30—H30B	109.5
C15—C16—H16	119.5	H30A—C30—H30B	109.5
C17—C16—H16	119.5	C29—C30—H30C	109.5
C16—C17—C18	119.7 (3)	H30A—C30—H30C	109.5
C16—C17—S3	119.3 (3)	H30B—C30—H30C	109.5
C18—C17—S3	121.0 (2)	C18—O1—C28	116.7 (2)
O1—C18—C13	120.0 (3)	C12—O2—H2A	109.5
O1—C18—C17	121.2 (3)	C6—O3—C25	116.5 (2)
C13—C18—C17	118.7 (3)	C24—O4—H4A	109.5
C20—C19—C24	119.9 (3)	C11—S4—C13	97.33 (15)
C20—C19—S3	119.8 (3)	C17—S3—C19	97.63 (15)
C24—C19—S3	120.3 (3)	C23—S2—C1	101.49 (15)
C21—C20—C19	120.0 (3)	C7—S1—C5	103.06 (15)
C6—C1—C2—C3	0.2 (5)	C16—C17—C18—C13	−4.5 (5)
S2—C1—C2—C3	−178.2 (3)	S3—C17—C18—C13	174.0 (2)
C1—C2—C3—C4	1.7 (6)	C24—C19—C20—C21	1.1 (5)
C2—C3—C4—C5	−1.3 (6)	S3—C19—C20—C21	−179.9 (3)
C3—C4—C5—C6	−0.9 (5)	C19—C20—C21—C22	−1.3 (5)
C3—C4—C5—S1	174.7 (3)	C19—C20—C21—Br2	179.5 (2)
C4—C5—C6—O3	−172.5 (3)	C20—C21—C22—C23	0.4 (5)
S1—C5—C6—O3	11.9 (4)	Br2—C21—C22—C23	179.6 (3)
C4—C5—C6—C1	2.9 (5)	C21—C22—C23—C24	0.5 (5)
S1—C5—C6—C1	−172.8 (2)	C21—C22—C23—S2	175.1 (3)
C2—C1—C6—O3	172.8 (3)	C20—C19—C24—O4	−179.9 (3)
S2—C1—C6—O3	−8.8 (4)	S3—C19—C24—O4	1.1 (4)
C2—C1—C6—C5	−2.5 (5)	C20—C19—C24—C23	−0.2 (5)
S2—C1—C6—C5	175.9 (2)	S3—C19—C24—C23	−179.1 (2)
C12—C7—C8—C9	−0.5 (5)	C22—C23—C24—O4	179.1 (3)
S1—C7—C8—C9	−176.1 (3)	S2—C23—C24—O4	4.5 (5)
C7—C8—C9—C10	−1.1 (5)	C22—C23—C24—C19	−0.6 (5)
C7—C8—C9—Br1	−178.9 (3)	S2—C23—C24—C19	−175.2 (2)
C8—C9—C10—C11	1.1 (5)	O3—C25—C26—C27	−173.3 (4)
Br1—C9—C10—C11	178.9 (3)	O1—C28—C29—C30	59.9 (4)
C9—C10—C11—C12	0.4 (5)	C13—C18—O1—C28	−96.9 (3)
C9—C10—C11—S4	−177.2 (3)	C17—C18—O1—C28	86.8 (4)
C8—C7—C12—O2	−179.5 (3)	C29—C28—O1—C18	−171.2 (3)
S1—C7—C12—O2	−3.9 (5)	C5—C6—O3—C25	−91.0 (4)
C8—C7—C12—C11	1.9 (5)	C1—C6—O3—C25	93.7 (4)
S1—C7—C12—C11	177.5 (2)	C26—C25—O3—C6	176.1 (3)
C10—C11—C12—O2	179.4 (3)	C10—C11—S4—C13	111.1 (3)
S4—C11—C12—O2	−2.9 (4)	C12—C11—S4—C13	−66.5 (3)
C10—C11—C12—C7	−1.9 (5)	C14—C13—S4—C11	−44.9 (3)
S4—C11—C12—C7	175.8 (3)	C18—C13—S4—C11	133.3 (3)
C18—C13—C14—C15	−0.9 (5)	C16—C17—S3—C19	49.0 (3)
S4—C13—C14—C15	177.3 (3)	C18—C17—S3—C19	−129.5 (3)
C13—C14—C15—C16	−0.8 (5)	C20—C19—S3—C17	−114.9 (3)
C14—C15—C16—C17	−0.2 (5)	C24—C19—S3—C17	64.0 (3)
C15—C16—C17—C18	2.9 (5)	C22—C23—S2—C1	109.2 (3)
C15—C16—C17—S3	−175.6 (3)	C24—C23—S2—C1	−76.2 (3)
C14—C13—C18—O1	−172.8 (3)	C2—C1—S2—C23	−74.2 (3)
S4—C13—C18—O1	9.0 (4)	C6—C1—S2—C23	107.5 (3)
C14—C13—C18—C17	3.6 (5)	C8—C7—S1—C5	−110.4 (3)
S4—C13—C18—C17	−174.6 (2)	C12—C7—S1—C5	74.0 (3)
C16—C17—C18—O1	171.8 (3)	C4—C5—S1—C7	78.8 (3)
S3—C17—C18—O1	−9.7 (4)	C6—C5—S1—C7	−105.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.82	2.20	2.926 (3)	148
O2—H2A···O3	0.82	2.12	2.849 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3	0.82	2.20	2.926 (3)	148
O2—H2A⋯O3	0.82	2.12	2.849 (3)	148