(Adamantan-1-yl)(phenyl-sulfan-yl)methanone.

Two independent mol-ecules (A and B) comprises the asymmetric unit of the title ester, C(17)H(20)OS. The phenyl ring is inclined with respect to the thio-carboxyl group, forming dihedral angles of 58.95 (6) (in mol-ecule A) and 62.28 (6)° (in mol-ecule B). In each independent mol-ecule, one adamantyl methyl-ene C atom is nearly coplanar with the thio-carboxyl group. The major difference between mol-ecules A and B relates to the relationship between the S atom and the coplanar adamantyl methyl-ene C atom [C(a)-C(q)-C(c)-S torsion angles = 178.25 (8) and 6.81 (13)°, respectively; C(a) = adamantyl methyl-ene C atom, C(q) = quaternary C atom and C(c) = carbonyl C atom], whereby the S atom in mol-ecule A has an anti relationship with the methyl-ene C atom and in mol-ecule B, the S atom is syn. In the crystal, C-H⋯π inter-actions are formed leading to supra-molecular layers in the ac plane.

Related literature

For applications of thio­esters in organic synthesis, see: Shah et al. (2002 ▶); Manabe et al. (2007 ▶); Horst et al. (2007 ▶). For the synthesis, see: El-Azab & Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C17H20OS

M = 272.39

Monoclinic,

a = 6.3545 (1) Å

b = 39.4559 (5) Å

c = 11.3878 (1) Å

β = 99.879 (1)°

V = 2812.84 (6) Å3

Z = 8

Cu Kα radiation

μ = 1.94 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.881, T max = 1.000

11270 measured reflections

5753 independent reflections

5445 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.02

5753 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and QMol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026116/xu5558sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026116/xu5558Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026116/xu5558Isup3.cml

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

C17H20OS	F(000) = 1168
Mr = 272.39	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7141 reflections
a = 6.3545 (1) Å	θ = 4.5–76.4°
b = 39.4559 (5) Å	µ = 1.94 mm−1
c = 11.3878 (1) Å	T = 100 K
β = 99.879 (1)°	Prism, colourless
V = 2812.84 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	5753 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5445 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −47→48
Tmin = 0.881, Tmax = 1.000	l = −8→14
11270 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0484P)2 + 1.0716P] where P = (Fo2 + 2Fc2)/3
5753 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.46660 (5)	0.389463 (8)	0.15443 (3)	0.02399 (9)
S2	0.08761 (5)	0.329812 (7)	0.36140 (3)	0.02206 (9)
O1	0.76535 (15)	0.39786 (2)	0.02056 (8)	0.0241 (2)
O2	0.44170 (15)	0.29759 (2)	0.45497 (8)	0.0251 (2)
C1	0.76163 (18)	0.44208 (3)	0.16696 (10)	0.0137 (2)
C2	0.95311 (18)	0.45667 (3)	0.11779 (10)	0.0166 (2)
H2A	1.0706	0.4399	0.1275	0.020*
H2B	0.9109	0.4616	0.0317	0.020*
C3	1.02995 (18)	0.48936 (3)	0.18489 (10)	0.0171 (2)
H3	1.1546	0.4987	0.1525	0.021*
C4	1.09809 (19)	0.48149 (3)	0.31807 (11)	0.0190 (2)
H4A	1.2160	0.4648	0.3291	0.023*
H4B	1.1499	0.5024	0.3616	0.023*
C5	0.90662 (19)	0.46717 (3)	0.36777 (10)	0.0174 (2)
H5	0.9507	0.4621	0.4546	0.021*
C6	0.72444 (19)	0.49318 (3)	0.35115 (10)	0.0179 (2)
H6A	0.6010	0.4840	0.3834	0.021*
H6B	0.7723	0.5142	0.3953	0.021*
C7	0.65749 (18)	0.50116 (3)	0.21815 (11)	0.0168 (2)
H7	0.5391	0.5182	0.2075	0.020*
C8	0.58022 (18)	0.46848 (3)	0.15095 (10)	0.0152 (2)
H8A	0.5350	0.4735	0.0652	0.018*
H8B	0.4557	0.4593	0.1820	0.018*
C9	0.82946 (19)	0.43447 (3)	0.30135 (10)	0.0162 (2)
H9A	0.7068	0.4250	0.3337	0.019*
H9B	0.9456	0.4174	0.3129	0.019*
C10	0.84922 (19)	0.51560 (3)	0.16903 (11)	0.0182 (2)
H10A	0.8063	0.5211	0.0835	0.022*
H10B	0.8992	0.5367	0.2121	0.022*
C11	0.68647 (18)	0.40943 (3)	0.10050 (10)	0.0157 (2)
C12	0.4232 (2)	0.35256 (3)	0.06489 (10)	0.0186 (2)
C13	0.2217 (2)	0.34757 (3)	−0.00245 (11)	0.0219 (3)
H13	0.1133	0.3642	−0.0035	0.026*
C14	0.1807 (2)	0.31787 (4)	−0.06838 (12)	0.0280 (3)
H14	0.0429	0.3141	−0.1140	0.034*
C15	0.3390 (3)	0.29386 (3)	−0.06799 (12)	0.0310 (3)
H15	0.3103	0.2737	−0.1138	0.037*
C16	0.5399 (3)	0.29911 (3)	−0.00078 (12)	0.0298 (3)
H16	0.6485	0.2826	−0.0010	0.036*
C17	0.5832 (2)	0.32837 (3)	0.06684 (11)	0.0232 (3)
H17	0.7201	0.3318	0.1138	0.028*
C18	0.41351 (18)	0.35295 (3)	0.54008 (10)	0.0144 (2)
C19	0.61791 (19)	0.36792 (3)	0.50444 (10)	0.0169 (2)
H19A	0.7273	0.3500	0.5068	0.020*
H19B	0.5855	0.3769	0.4221	0.020*
C20	0.70394 (19)	0.39656 (3)	0.59103 (11)	0.0183 (2)
H20	0.8358	0.4063	0.5674	0.022*
C21	0.7582 (2)	0.38215 (3)	0.71780 (11)	0.0211 (3)
H21A	0.8683	0.3643	0.7206	0.025*
H21B	0.8163	0.4003	0.7740	0.025*
C22	0.5563 (2)	0.36727 (3)	0.75447 (10)	0.0197 (2)
H22	0.5920	0.3579	0.8370	0.024*
C23	0.3884 (2)	0.39527 (3)	0.75166 (11)	0.0198 (2)
H23A	0.2581	0.3859	0.7763	0.024*
H23B	0.4446	0.4135	0.8080	0.024*
C24	0.33386 (19)	0.40958 (3)	0.62496 (11)	0.0174 (2)
H24	0.2234	0.4277	0.6227	0.021*
C25	0.24680 (19)	0.38120 (3)	0.53755 (11)	0.0183 (2)
H25A	0.1146	0.3718	0.5597	0.022*
H25B	0.2110	0.3906	0.4559	0.022*
C26	0.4675 (2)	0.33886 (3)	0.66795 (10)	0.0180 (2)
H26A	0.3372	0.3292	0.6918	0.022*
H26B	0.5745	0.3205	0.6710	0.022*
C27	0.5349 (2)	0.42451 (3)	0.58783 (11)	0.0189 (2)
H27A	0.5915	0.4430	0.6429	0.023*
H27B	0.4996	0.4340	0.5064	0.023*
C28	0.33992 (19)	0.32324 (3)	0.45677 (10)	0.0164 (2)
C29	0.0397 (2)	0.29028 (3)	0.28765 (11)	0.0189 (2)
C30	−0.1416 (2)	0.27231 (3)	0.30447 (11)	0.0228 (3)
H30	−0.2272	0.2802	0.3595	0.027*
C31	−0.1958 (2)	0.24277 (3)	0.23994 (12)	0.0257 (3)
H31	−0.3202	0.2306	0.2502	0.031*
C32	−0.0694 (2)	0.23103 (3)	0.16072 (11)	0.0247 (3)
H32	−0.1073	0.2108	0.1169	0.030*
C33	0.1126 (2)	0.24884 (3)	0.14535 (11)	0.0232 (3)
H33	0.2001	0.2406	0.0919	0.028*
C34	0.1671 (2)	0.27874 (3)	0.20787 (11)	0.0213 (3)
H34	0.2899	0.2912	0.1963	0.026*

	U11	U22	U33	U12	U13	U23
S1	0.02653 (17)	0.02207 (16)	0.02655 (16)	−0.00994 (12)	0.01353 (13)	−0.01064 (12)
S2	0.02095 (16)	0.01698 (15)	0.02578 (16)	0.00343 (11)	−0.00291 (12)	−0.00611 (11)
O1	0.0261 (5)	0.0264 (5)	0.0218 (4)	−0.0040 (4)	0.0103 (4)	−0.0081 (4)
O2	0.0249 (5)	0.0175 (4)	0.0313 (5)	0.0064 (4)	0.0003 (4)	−0.0048 (4)
C1	0.0128 (5)	0.0158 (5)	0.0128 (5)	−0.0002 (4)	0.0028 (4)	0.0004 (4)
C2	0.0142 (5)	0.0201 (6)	0.0166 (5)	−0.0003 (4)	0.0056 (4)	−0.0003 (4)
C3	0.0122 (5)	0.0201 (6)	0.0197 (6)	−0.0026 (4)	0.0049 (4)	0.0011 (4)
C4	0.0140 (5)	0.0217 (6)	0.0200 (6)	−0.0027 (4)	−0.0006 (4)	−0.0001 (5)
C5	0.0187 (6)	0.0194 (6)	0.0134 (5)	−0.0034 (5)	0.0012 (4)	0.0003 (4)
C6	0.0182 (6)	0.0177 (6)	0.0188 (6)	−0.0042 (4)	0.0063 (4)	−0.0043 (4)
C7	0.0135 (5)	0.0152 (5)	0.0222 (6)	0.0003 (4)	0.0039 (4)	0.0001 (4)
C8	0.0118 (5)	0.0166 (5)	0.0170 (5)	0.0000 (4)	0.0019 (4)	0.0010 (4)
C9	0.0181 (6)	0.0158 (5)	0.0143 (5)	−0.0007 (4)	0.0011 (4)	0.0017 (4)
C10	0.0177 (6)	0.0166 (5)	0.0208 (6)	−0.0016 (4)	0.0043 (4)	0.0031 (4)
C11	0.0150 (5)	0.0176 (5)	0.0141 (5)	0.0010 (4)	0.0015 (4)	0.0011 (4)
C12	0.0259 (6)	0.0151 (5)	0.0156 (5)	−0.0034 (5)	0.0056 (5)	−0.0006 (4)
C13	0.0259 (7)	0.0192 (6)	0.0207 (6)	−0.0040 (5)	0.0047 (5)	0.0023 (5)
C14	0.0381 (8)	0.0264 (7)	0.0185 (6)	−0.0132 (6)	0.0022 (5)	−0.0001 (5)
C15	0.0594 (10)	0.0170 (6)	0.0189 (6)	−0.0095 (6)	0.0129 (6)	−0.0028 (5)
C16	0.0490 (9)	0.0176 (6)	0.0266 (7)	0.0070 (6)	0.0172 (6)	0.0043 (5)
C17	0.0282 (7)	0.0225 (6)	0.0193 (6)	0.0025 (5)	0.0051 (5)	0.0048 (5)
C18	0.0143 (5)	0.0132 (5)	0.0163 (5)	0.0014 (4)	0.0045 (4)	0.0008 (4)
C19	0.0172 (6)	0.0164 (5)	0.0188 (5)	0.0003 (4)	0.0082 (4)	0.0011 (4)
C20	0.0148 (6)	0.0181 (6)	0.0235 (6)	−0.0023 (4)	0.0077 (4)	−0.0009 (5)
C21	0.0165 (6)	0.0226 (6)	0.0230 (6)	0.0021 (5)	−0.0005 (5)	−0.0026 (5)
C22	0.0258 (6)	0.0191 (6)	0.0142 (5)	0.0009 (5)	0.0036 (5)	0.0022 (4)
C23	0.0211 (6)	0.0202 (6)	0.0202 (6)	−0.0018 (5)	0.0094 (5)	−0.0034 (5)
C24	0.0154 (6)	0.0144 (5)	0.0227 (6)	0.0022 (4)	0.0040 (4)	−0.0023 (4)
C25	0.0152 (6)	0.0162 (5)	0.0226 (6)	0.0033 (4)	0.0012 (4)	−0.0025 (4)
C26	0.0228 (6)	0.0152 (5)	0.0171 (5)	0.0007 (4)	0.0061 (5)	0.0032 (4)
C27	0.0219 (6)	0.0135 (5)	0.0222 (6)	−0.0010 (4)	0.0064 (5)	0.0001 (4)
C28	0.0166 (6)	0.0163 (5)	0.0173 (5)	0.0006 (4)	0.0056 (4)	0.0015 (4)
C29	0.0226 (6)	0.0155 (5)	0.0173 (5)	0.0011 (5)	−0.0002 (4)	−0.0013 (4)
C30	0.0231 (6)	0.0239 (6)	0.0216 (6)	0.0000 (5)	0.0042 (5)	−0.0021 (5)
C31	0.0266 (7)	0.0236 (6)	0.0271 (7)	−0.0061 (5)	0.0051 (5)	−0.0014 (5)
C32	0.0355 (7)	0.0171 (6)	0.0204 (6)	−0.0037 (5)	0.0019 (5)	−0.0023 (5)
C33	0.0338 (7)	0.0190 (6)	0.0180 (6)	0.0010 (5)	0.0078 (5)	0.0000 (5)
C34	0.0261 (6)	0.0181 (6)	0.0203 (6)	−0.0011 (5)	0.0060 (5)	0.0024 (5)

S1—C12	1.7717 (12)	C16—C17	1.3888 (19)
S1—C11	1.8011 (12)	C16—H16	0.9500
S2—C29	1.7729 (12)	C17—H17	0.9500
S2—C28	1.7944 (12)	C18—C28	1.5298 (16)
O1—C11	1.2021 (15)	C18—C25	1.5348 (15)
O2—C28	1.2033 (15)	C18—C19	1.5432 (15)
C1—C11	1.5284 (15)	C18—C26	1.5413 (15)
C1—C2	1.5360 (15)	C19—C20	1.5373 (16)
C1—C8	1.5413 (15)	C19—H19A	0.9900
C1—C9	1.5465 (15)	C19—H19B	0.9900
C2—C3	1.5357 (16)	C20—C21	1.5347 (17)
C2—H2A	0.9900	C20—C27	1.5356 (16)
C2—H2B	0.9900	C20—H20	1.0000
C3—C10	1.5337 (16)	C21—C22	1.5331 (17)
C3—C4	1.5359 (16)	C21—H21A	0.9900
C3—H3	1.0000	C21—H21B	0.9900
C4—C5	1.5349 (16)	C22—C26	1.5343 (17)
C4—H4A	0.9900	C22—C23	1.5322 (17)
C4—H4B	0.9900	C22—H22	1.0000
C5—C9	1.5330 (16)	C23—C24	1.5328 (17)
C5—C6	1.5343 (17)	C23—H23A	0.9900
C5—H5	1.0000	C23—H23B	0.9900
C6—C7	1.5339 (16)	C24—C27	1.5308 (16)
C6—H6A	0.9900	C24—C25	1.5368 (16)
C6—H6B	0.9900	C24—H24	1.0000
C7—C10	1.5349 (16)	C25—H25A	0.9900
C7—C8	1.5362 (16)	C25—H25B	0.9900
C7—H7	1.0000	C26—H26A	0.9900
C8—H8A	0.9900	C26—H26B	0.9900
C8—H8B	0.9900	C27—H27A	0.9900
C9—H9A	0.9900	C27—H27B	0.9900
C9—H9B	0.9900	C29—C30	1.3937 (18)
C10—H10A	0.9900	C29—C34	1.3926 (18)
C10—H10B	0.9900	C30—C31	1.3891 (18)
C12—C13	1.3894 (18)	C30—H30	0.9500
C12—C17	1.3917 (18)	C31—C32	1.386 (2)
C13—C14	1.3919 (18)	C31—H31	0.9500
C13—H13	0.9500	C32—C33	1.3902 (19)
C14—C15	1.381 (2)	C32—H32	0.9500
C14—H14	0.9500	C33—C34	1.3907 (18)
C15—C16	1.386 (2)	C33—H33	0.9500
C15—H15	0.9500	C34—H34	0.9500
C12—S1—C11	102.49 (6)	C12—C17—H17	120.4
C29—S2—C28	102.86 (6)	C28—C18—C25	114.10 (10)
C11—C1—C2	109.59 (9)	C28—C18—C19	108.16 (9)
C11—C1—C8	110.32 (9)	C25—C18—C19	109.05 (9)
C2—C1—C8	109.07 (9)	C28—C18—C26	107.72 (9)
C11—C1—C9	109.68 (9)	C25—C18—C26	108.69 (9)
C2—C1—C9	109.26 (9)	C19—C18—C26	109.00 (9)
C8—C1—C9	108.91 (9)	C20—C19—C18	109.60 (9)
C3—C2—C1	109.73 (9)	C20—C19—H19A	109.8
C3—C2—H2A	109.7	C18—C19—H19A	109.8
C1—C2—H2A	109.7	C20—C19—H19B	109.8
C3—C2—H2B	109.7	C18—C19—H19B	109.8
C1—C2—H2B	109.7	H19A—C19—H19B	108.2
H2A—C2—H2B	108.2	C21—C20—C27	109.38 (10)
C10—C3—C2	109.92 (10)	C21—C20—C19	109.20 (10)
C10—C3—C4	109.36 (10)	C27—C20—C19	110.03 (10)
C2—C3—C4	109.45 (10)	C21—C20—H20	109.4
C10—C3—H3	109.4	C27—C20—H20	109.4
C2—C3—H3	109.4	C19—C20—H20	109.4
C4—C3—H3	109.4	C22—C21—C20	109.54 (10)
C5—C4—C3	109.37 (9)	C22—C21—H21A	109.8
C5—C4—H4A	109.8	C20—C21—H21A	109.8
C3—C4—H4A	109.8	C22—C21—H21B	109.8
C5—C4—H4B	109.8	C20—C21—H21B	109.8
C3—C4—H4B	109.8	H21A—C21—H21B	108.2
H4A—C4—H4B	108.2	C21—C22—C26	109.73 (10)
C9—C5—C6	109.35 (9)	C21—C22—C23	109.30 (10)
C9—C5—C4	109.55 (10)	C26—C22—C23	109.58 (10)
C6—C5—C4	109.72 (10)	C21—C22—H22	109.4
C9—C5—H5	109.4	C26—C22—H22	109.4
C6—C5—H5	109.4	C23—C22—H22	109.4
C4—C5—H5	109.4	C24—C23—C22	109.24 (9)
C7—C6—C5	109.55 (9)	C24—C23—H23A	109.8
C7—C6—H6A	109.8	C22—C23—H23A	109.8
C5—C6—H6A	109.8	C24—C23—H23B	109.8
C7—C6—H6B	109.8	C22—C23—H23B	109.8
C5—C6—H6B	109.8	H23A—C23—H23B	108.3
H6A—C6—H6B	108.2	C27—C24—C23	109.71 (10)
C6—C7—C10	109.45 (9)	C27—C24—C25	109.04 (10)
C6—C7—C8	109.29 (9)	C23—C24—C25	109.83 (10)
C10—C7—C8	109.63 (10)	C27—C24—H24	109.4
C6—C7—H7	109.5	C23—C24—H24	109.4
C10—C7—H7	109.5	C25—C24—H24	109.4
C8—C7—H7	109.5	C18—C25—C24	110.28 (9)
C7—C8—C1	109.86 (9)	C18—C25—H25A	109.6
C7—C8—H8A	109.7	C24—C25—H25A	109.6
C1—C8—H8A	109.7	C18—C25—H25B	109.6
C7—C8—H8B	109.7	C24—C25—H25B	109.6
C1—C8—H8B	109.7	H25A—C25—H25B	108.1
H8A—C8—H8B	108.2	C22—C26—C18	109.94 (9)
C5—C9—C1	109.64 (9)	C22—C26—H26A	109.7
C5—C9—H9A	109.7	C18—C26—H26A	109.7
C1—C9—H9A	109.7	C22—C26—H26B	109.7
C5—C9—H9B	109.7	C18—C26—H26B	109.7
C1—C9—H9B	109.7	H26A—C26—H26B	108.2
H9A—C9—H9B	108.2	C24—C27—C20	109.31 (9)
C3—C10—C7	109.37 (9)	C24—C27—H27A	109.8
C3—C10—H10A	109.8	C20—C27—H27A	109.8
C7—C10—H10A	109.8	C24—C27—H27B	109.8
C3—C10—H10B	109.8	C20—C27—H27B	109.8
C7—C10—H10B	109.8	H27A—C27—H27B	108.3
H10A—C10—H10B	108.2	O2—C28—C18	123.17 (11)
O1—C11—C1	124.03 (11)	O2—C28—S2	122.56 (9)
O1—C11—S1	122.73 (9)	C18—C28—S2	114.26 (8)
C1—C11—S1	113.24 (8)	C30—C29—C34	120.65 (11)
C13—C12—C17	120.87 (12)	C30—C29—S2	117.47 (10)
C13—C12—S1	118.15 (10)	C34—C29—S2	121.66 (10)
C17—C12—S1	120.90 (10)	C31—C30—C29	119.34 (12)
C12—C13—C14	119.10 (13)	C31—C30—H30	120.3
C12—C13—H13	120.4	C29—C30—H30	120.3
C14—C13—H13	120.4	C32—C31—C30	120.40 (12)
C15—C14—C13	120.47 (13)	C32—C31—H31	119.8
C15—C14—H14	119.8	C30—C31—H31	119.8
C13—C14—H14	119.8	C31—C32—C33	120.01 (12)
C14—C15—C16	120.01 (12)	C31—C32—H32	120.0
C14—C15—H15	120.0	C33—C32—H32	120.0
C16—C15—H15	120.0	C34—C33—C32	120.26 (12)
C15—C16—C17	120.42 (13)	C34—C33—H33	119.9
C15—C16—H16	119.8	C32—C33—H33	119.9
C17—C16—H16	119.8	C33—C34—C29	119.33 (12)
C16—C17—C12	119.13 (13)	C33—C34—H34	120.3
C16—C17—H17	120.4	C29—C34—H34	120.3
C11—C1—C2—C3	−179.65 (9)	C28—C18—C19—C20	−176.73 (9)
C8—C1—C2—C3	59.48 (12)	C25—C18—C19—C20	58.66 (12)
C9—C1—C2—C3	−59.46 (12)	C26—C18—C19—C20	−59.87 (12)
C1—C2—C3—C10	−59.96 (12)	C18—C19—C20—C21	60.67 (12)
C1—C2—C3—C4	60.17 (12)	C18—C19—C20—C27	−59.40 (12)
C10—C3—C4—C5	60.16 (12)	C27—C20—C21—C22	60.01 (13)
C2—C3—C4—C5	−60.31 (12)	C19—C20—C21—C22	−60.45 (12)
C3—C4—C5—C9	60.34 (12)	C20—C21—C22—C26	59.90 (13)
C3—C4—C5—C6	−59.71 (12)	C20—C21—C22—C23	−60.30 (13)
C9—C5—C6—C7	−60.61 (12)	C21—C22—C23—C24	60.27 (12)
C4—C5—C6—C7	59.56 (12)	C26—C22—C23—C24	−60.02 (12)
C5—C6—C7—C10	−59.76 (12)	C22—C23—C24—C27	−60.40 (12)
C5—C6—C7—C8	60.31 (12)	C22—C23—C24—C25	59.43 (12)
C6—C7—C8—C1	−60.07 (12)	C28—C18—C25—C24	179.25 (9)
C10—C7—C8—C1	59.89 (12)	C19—C18—C25—C24	−59.70 (12)
C11—C1—C8—C7	179.96 (9)	C26—C18—C25—C24	59.03 (12)
C2—C1—C8—C7	−59.63 (12)	C27—C24—C25—C18	60.66 (12)
C9—C1—C8—C7	59.53 (12)	C23—C24—C25—C18	−59.58 (13)
C6—C5—C9—C1	60.35 (12)	C21—C22—C26—C18	−59.45 (13)
C4—C5—C9—C1	−59.92 (12)	C23—C22—C26—C18	60.57 (12)
C11—C1—C9—C5	179.52 (9)	C28—C18—C26—C22	176.34 (9)
C2—C1—C9—C5	59.38 (12)	C25—C18—C26—C22	−59.56 (12)
C8—C1—C9—C5	−59.66 (12)	C19—C18—C26—C22	59.20 (12)
C2—C3—C10—C7	59.66 (12)	C23—C24—C27—C20	60.11 (12)
C4—C3—C10—C7	−60.52 (12)	C25—C24—C27—C20	−60.21 (12)
C6—C7—C10—C3	60.32 (12)	C21—C20—C27—C24	−59.75 (13)
C8—C7—C10—C3	−59.55 (12)	C19—C20—C27—C24	60.20 (12)
C2—C1—C11—O1	−1.39 (16)	C25—C18—C28—O2	−173.14 (11)
C8—C1—C11—O1	118.72 (12)	C19—C18—C28—O2	65.32 (14)
C9—C1—C11—O1	−121.32 (12)	C26—C18—C28—O2	−52.37 (15)
C2—C1—C11—S1	178.25 (8)	C25—C18—C28—S2	6.81 (13)
C8—C1—C11—S1	−61.65 (10)	C19—C18—C28—S2	−114.73 (9)
C9—C1—C11—S1	58.32 (11)	C26—C18—C28—S2	127.58 (9)
C12—S1—C11—O1	1.36 (12)	C29—S2—C28—O2	4.68 (12)
C12—S1—C11—C1	−178.29 (8)	C29—S2—C28—C18	−175.27 (8)
C11—S1—C12—C13	−122.88 (10)	C28—S2—C29—C30	118.64 (10)
C11—S1—C12—C17	60.50 (11)	C28—S2—C29—C34	−66.73 (11)
C17—C12—C13—C14	0.09 (18)	C34—C29—C30—C31	−0.55 (19)
S1—C12—C13—C14	−176.54 (9)	S2—C29—C30—C31	174.15 (10)
C12—C13—C14—C15	−0.74 (19)	C29—C30—C31—C32	0.8 (2)
C13—C14—C15—C16	0.6 (2)	C30—C31—C32—C33	−0.1 (2)
C14—C15—C16—C17	0.3 (2)	C31—C32—C33—C34	−1.0 (2)
C15—C16—C17—C12	−0.92 (19)	C32—C33—C34—C29	1.24 (19)
C13—C12—C17—C16	0.74 (18)	C30—C29—C34—C33	−0.48 (19)
S1—C12—C17—C16	177.27 (10)	S2—C29—C34—C33	−174.95 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1i	1.00	2.81	3.6129 (13)	138
C34—H34···Cg1	0.95	2.73	3.4234 (14)	131
C15—H15···Cg2ii	0.95	2.86	3.6668 (16)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12–C17 and C29–C34 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯Cg1i	1.00	2.81	3.6129 (13)	138
C34—H34⋯Cg1	0.95	2.73	3.4234 (14)	131
C15—H15⋯Cg2ii	0.95	2.86	3.6668 (16)	143

Symmetry codes: (i) ; (ii) .