1-(4-Methoxy­phen­yl)-3,3-bis­(methyl­sulfan­yl)-2-phenyl­prop-2-en-1-one

In the title compound, C₁₈H₁₈O₂S₂, there are two independent and conformationally similar mol­ecules in the asymmetric unit. In one of the mol­ecules, the dihedral angle between the two aromatic rings is 77.1 (2)°, and in the other it is 78.2 (2)°. The two independent mol­ecules are linked by a C—H...π inter­action.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.172
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5B    -   C6B     ..       7.20 su

Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

1-(4-Methoxyphenyl)-3,3-bis(methylsulfanyl)-2-phenylprop-2-en-1-one

Crystal data

C18H18O2S2	F(000) = 1392
Mr = 330.44	Dx = 1.296 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yab	Cell parameters from 25 reflections
a = 16.471 (3) Å	θ = 1.0–29.0°
b = 9.879 (4) Å	µ = 0.32 mm^−1
c = 22.065 (8) Å	T = 293 K
β = 109.362 (17)°	Block, yellow
V = 3387.2 (19) Å^3	0.24 × 0.22 × 0.19 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 29.0°, θmin = 1.0°
Graphite monochromator	h = 0→22
ω scans	k = 0→13
9240 measured reflections	l = −30→28
8931 independent reflections	3 standard reflections every 60 min
4621 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0896P)^2 + 0.1171P] where P = (Fo^2 + 2Fc^2)/3
8931 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. The IR spectrum showed a band at 1684 cm-1 due to the carbonyl group and band at 1605 cm-1 due to carbon carbon double bond. Its 1H-NMR spectrum exhibited two 6H singlets at δ 2.23 and δ 2.28 due to two S-methyl H atoms, a 3H singlet at δ 3.84 due to methoxy H atoms, and a 9H multiplet at δ 6.91–7.96 due to aromatic H atoms. Its mass spectrum showed molecular ion peak at m/z 330.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1A	0.10263 (5)	0.29082 (8)	0.48121 (3)	0.0666 (2)
S2A	0.08739 (5)	0.25045 (8)	0.34099 (3)	0.0663 (2)
O1A	0.29582 (16)	0.1729 (2)	0.36310 (11)	0.0864 (7)
O2A	0.34727 (13)	0.76805 (19)	0.28180 (10)	0.0700 (5)
C1A	0.23768 (15)	0.2816 (2)	0.43549 (11)	0.0514 (6)
C2A	0.30346 (16)	0.2865 (3)	0.50063 (12)	0.0558 (6)
C3A	0.29992 (19)	0.3836 (3)	0.54528 (13)	0.0673 (7)
H3A	0.2554	0.4466	0.5345	0.081*
C4A	0.3615 (3)	0.3875 (4)	0.60503 (15)	0.0925 (12)
H4A	0.3580	0.4516	0.6350	0.111*
C5A	0.4285 (3)	0.2959 (5)	0.62059 (18)	0.1089 (16)
H5A	0.4705	0.2989	0.6610	0.131*
C6A	0.4334 (2)	0.2005 (5)	0.5767 (2)	0.1048 (14)
H6A	0.4786	0.1388	0.5875	0.126*
C7A	0.37103 (18)	0.1958 (3)	0.51647 (16)	0.0745 (8)
H7A	0.3747	0.1315	0.4867	0.089*
C8A	0.27609 (16)	0.2793 (3)	0.38139 (12)	0.0563 (6)
C9A	0.29304 (14)	0.4099 (2)	0.35643 (11)	0.0481 (5)
C10A	0.26504 (18)	0.5301 (3)	0.37382 (12)	0.0619 (7)
H10A	0.2344	0.5292	0.4024	0.074*
C11A	0.28126 (19)	0.6513 (3)	0.34999 (14)	0.0657 (7)
H11A	0.2616	0.7315	0.3623	0.079*
C12A	0.32706 (15)	0.6542 (3)	0.30751 (12)	0.0532 (6)
C13A	0.35610 (17)	0.5340 (3)	0.28990 (12)	0.0592 (6)
H13A	0.3875	0.5350	0.2618	0.071*
C14A	0.33899 (16)	0.4148 (3)	0.31355 (11)	0.0539 (6)
H14A	0.3583	0.3347	0.3009	0.065*
C15A	0.3168 (2)	0.8927 (3)	0.29752 (17)	0.0870 (10)
H15A	0.3352	0.9652	0.2761	0.130*
H15B	0.3395	0.9064	0.3431	0.130*
H15C	0.2551	0.8911	0.2840	0.130*
C16A	0.15323 (16)	0.2774 (3)	0.42217 (11)	0.0528 (6)
C17A	0.0373 (2)	0.1430 (3)	0.46781 (17)	0.0827 (9)
H17A	0.0066	0.1406	0.4980	0.124*
H17B	0.0730	0.0641	0.4733	0.124*
H17C	−0.0031	0.1446	0.4249	0.124*
C18A	0.0054 (2)	0.3763 (3)	0.32782 (16)	0.0845 (9)
H18A	−0.0337	0.3692	0.2846	0.127*
H18B	0.0313	0.4645	0.3344	0.127*
H18C	−0.0254	0.3627	0.3574	0.127*
S1B	0.11701 (4)	0.28229 (9)	0.02277 (3)	0.0697 (2)
S2B	0.22673 (5)	0.23672 (8)	0.16264 (3)	0.0645 (2)
O1B	0.41220 (14)	0.1525 (2)	0.14058 (11)	0.0829 (6)
O2B	0.54948 (15)	0.7431 (2)	0.21339 (11)	0.0847 (7)
C1B	0.29231 (15)	0.2643 (3)	0.06705 (12)	0.0529 (6)
C2B	0.29988 (16)	0.2702 (3)	0.00176 (13)	0.0569 (6)
C3B	0.25708 (19)	0.3657 (3)	−0.04290 (14)	0.0681 (7)
H3B	0.2221	0.4289	−0.0324	0.082*
C4B	0.2656 (2)	0.3689 (4)	−0.10345 (15)	0.0855 (10)
H4B	0.2358	0.4334	−0.1332	0.103*
C5B	0.3172 (3)	0.2783 (5)	−0.11936 (17)	0.0947 (12)
H5B	0.3223	0.2798	−0.1601	0.114*
C6B	0.3614 (2)	0.1850 (4)	−0.07505 (19)	0.0971 (12)
H6B	0.3973	0.1236	−0.0857	0.117*
C7B	0.35363 (19)	0.1804 (3)	−0.01411 (15)	0.0722 (8)
H7B	0.3846	0.1170	0.0158	0.087*
C8B	0.37829 (16)	0.2603 (3)	0.12102 (12)	0.0562 (6)
C9B	0.41999 (14)	0.3899 (2)	0.14421 (11)	0.0465 (5)
C10B	0.38113 (16)	0.5115 (3)	0.12247 (11)	0.0553 (6)
H10B	0.3260	0.5124	0.0925	0.066*
C11B	0.42191 (18)	0.6315 (3)	0.14404 (13)	0.0603 (7)
H11B	0.3945	0.7130	0.1288	0.072*
C12B	0.50305 (18)	0.6313 (3)	0.18813 (12)	0.0585 (7)
C13B	0.54407 (17)	0.5100 (3)	0.21030 (12)	0.0646 (7)
H13B	0.5996	0.5095	0.2398	0.078*
C14B	0.50270 (16)	0.3914 (3)	0.18863 (11)	0.0567 (6)
H14B	0.5302	0.3099	0.2038	0.068*
C15B	0.5076 (3)	0.8697 (4)	0.1970 (2)	0.1086 (14)
H15D	0.5466	0.9410	0.2177	0.163*
H15E	0.4581	0.8722	0.2108	0.163*
H15F	0.4897	0.8819	0.1512	0.163*
C16B	0.21969 (16)	0.2631 (3)	0.08147 (12)	0.0543 (6)
C17B	0.0620 (2)	0.1377 (3)	0.03621 (19)	0.0901 (10)
H17D	0.0043	0.1375	0.0065	0.135*
H17E	0.0606	0.1395	0.0794	0.135*
H17F	0.0914	0.0576	0.0301	0.135*
C18B	0.1628 (2)	0.3701 (3)	0.17691 (14)	0.0754 (8)
H18D	0.1626	0.3647	0.2203	0.113*
H18E	0.1050	0.3620	0.1477	0.113*
H18F	0.1864	0.4556	0.1704	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0709 (4)	0.0752 (5)	0.0616 (4)	−0.0159 (4)	0.0324 (3)	−0.0068 (3)
S2A	0.0644 (4)	0.0757 (5)	0.0517 (4)	−0.0044 (4)	0.0098 (3)	−0.0076 (3)
O1A	0.1219 (18)	0.0543 (12)	0.1049 (17)	0.0035 (12)	0.0670 (15)	−0.0088 (11)
O2A	0.0815 (13)	0.0591 (12)	0.0764 (13)	−0.0058 (10)	0.0355 (11)	0.0057 (10)
C1A	0.0541 (14)	0.0483 (14)	0.0524 (13)	−0.0056 (11)	0.0186 (11)	0.0017 (11)
C2A	0.0538 (14)	0.0581 (15)	0.0523 (13)	−0.0154 (12)	0.0131 (11)	0.0118 (12)
C3A	0.0750 (18)	0.0682 (18)	0.0535 (15)	−0.0235 (15)	0.0144 (13)	0.0017 (13)
C4A	0.105 (3)	0.106 (3)	0.0554 (18)	−0.053 (2)	0.0115 (18)	0.0016 (18)
C5A	0.086 (3)	0.154 (4)	0.064 (2)	−0.055 (3)	−0.0047 (19)	0.035 (3)
C6A	0.0606 (19)	0.138 (4)	0.102 (3)	−0.009 (2)	0.0081 (19)	0.060 (3)
C7A	0.0574 (16)	0.078 (2)	0.084 (2)	−0.0063 (15)	0.0184 (15)	0.0215 (16)
C8A	0.0570 (14)	0.0571 (16)	0.0566 (14)	−0.0017 (12)	0.0211 (12)	−0.0066 (12)
C9A	0.0477 (12)	0.0531 (14)	0.0443 (12)	0.0016 (11)	0.0166 (10)	−0.0047 (10)
C10A	0.0767 (17)	0.0606 (16)	0.0639 (15)	0.0056 (14)	0.0440 (14)	−0.0023 (13)
C11A	0.084 (2)	0.0535 (16)	0.0725 (18)	0.0095 (14)	0.0439 (16)	−0.0028 (13)
C12A	0.0521 (14)	0.0574 (15)	0.0507 (13)	−0.0026 (12)	0.0180 (11)	−0.0005 (11)
C13A	0.0656 (16)	0.0651 (17)	0.0581 (14)	−0.0027 (13)	0.0356 (13)	−0.0058 (13)
C14A	0.0565 (14)	0.0580 (15)	0.0528 (14)	0.0039 (12)	0.0255 (11)	−0.0093 (12)
C15A	0.099 (2)	0.0552 (18)	0.109 (3)	0.0003 (17)	0.039 (2)	0.0082 (17)
C16A	0.0565 (14)	0.0555 (15)	0.0445 (12)	−0.0084 (12)	0.0143 (10)	−0.0015 (11)
C17A	0.078 (2)	0.075 (2)	0.113 (3)	−0.0139 (16)	0.0548 (19)	−0.0056 (18)
C18A	0.087 (2)	0.077 (2)	0.075 (2)	0.0081 (17)	0.0077 (17)	0.0113 (16)
S1B	0.0556 (4)	0.0873 (5)	0.0617 (4)	−0.0171 (4)	0.0135 (3)	−0.0039 (4)
S2B	0.0682 (4)	0.0732 (5)	0.0555 (4)	−0.0027 (3)	0.0249 (3)	−0.0027 (3)
O1B	0.0819 (14)	0.0517 (12)	0.1040 (17)	0.0081 (11)	0.0160 (12)	0.0036 (11)
O2B	0.0960 (16)	0.0791 (15)	0.0869 (15)	−0.0380 (13)	0.0410 (13)	−0.0284 (12)
C1B	0.0526 (13)	0.0510 (14)	0.0555 (14)	−0.0087 (11)	0.0184 (11)	−0.0112 (11)
C2B	0.0538 (13)	0.0612 (16)	0.0585 (14)	−0.0178 (12)	0.0224 (12)	−0.0172 (13)
C3B	0.0771 (18)	0.0663 (18)	0.0661 (17)	−0.0112 (15)	0.0307 (15)	−0.0067 (14)
C4B	0.098 (2)	0.095 (3)	0.0671 (19)	−0.025 (2)	0.0318 (18)	0.0033 (18)
C5B	0.105 (3)	0.126 (3)	0.067 (2)	−0.031 (3)	0.046 (2)	−0.019 (2)
C6B	0.090 (2)	0.120 (3)	0.098 (3)	−0.022 (2)	0.054 (2)	−0.048 (2)
C7B	0.0714 (18)	0.0763 (19)	0.0782 (19)	−0.0112 (15)	0.0372 (16)	−0.0180 (16)
C8B	0.0568 (14)	0.0550 (16)	0.0604 (15)	0.0034 (12)	0.0244 (12)	−0.0014 (12)
C9B	0.0445 (12)	0.0516 (14)	0.0441 (12)	0.0000 (10)	0.0155 (10)	0.0002 (10)
C10B	0.0518 (14)	0.0548 (15)	0.0517 (13)	0.0029 (12)	0.0070 (11)	−0.0007 (11)
C11B	0.0697 (17)	0.0524 (16)	0.0585 (15)	0.0027 (13)	0.0210 (13)	0.0048 (12)
C12B	0.0679 (16)	0.0635 (17)	0.0525 (14)	−0.0169 (13)	0.0313 (13)	−0.0095 (12)
C13B	0.0503 (14)	0.082 (2)	0.0539 (15)	−0.0086 (14)	0.0076 (11)	−0.0115 (14)
C14B	0.0517 (14)	0.0639 (17)	0.0512 (14)	0.0095 (12)	0.0128 (11)	0.0042 (12)
C15B	0.156 (4)	0.062 (2)	0.138 (3)	−0.039 (2)	0.089 (3)	−0.032 (2)
C16B	0.0540 (13)	0.0593 (15)	0.0500 (13)	−0.0093 (12)	0.0177 (11)	−0.0058 (11)
C17B	0.0612 (18)	0.080 (2)	0.123 (3)	−0.0223 (16)	0.0229 (18)	−0.013 (2)
C18B	0.0768 (19)	0.084 (2)	0.0700 (18)	0.0000 (16)	0.0310 (15)	−0.0127 (16)

Geometric parameters (Å, º)

S1A—C16A	1.769 (3)	S1B—C16B	1.767 (3)
S1A—C17A	1.780 (3)	S1B—C17B	1.768 (3)
S2A—C16A	1.780 (2)	S2B—C16B	1.775 (3)
S2A—C18A	1.786 (3)	S2B—C18B	1.778 (3)
O1A—C8A	1.208 (3)	O1B—C8B	1.214 (3)
O2A—C12A	1.350 (3)	O2B—C12B	1.354 (3)
O2A—C15A	1.415 (4)	O2B—C15B	1.417 (4)
C1A—C16A	1.323 (3)	C1B—C16B	1.336 (3)
C1A—C2A	1.487 (3)	C1B—C2B	1.488 (3)
C1A—C8A	1.525 (3)	C1B—C8B	1.519 (3)
C2A—C7A	1.381 (4)	C2B—C7B	1.377 (4)
C2A—C3A	1.390 (4)	C2B—C3B	1.378 (4)
C3A—C4A	1.372 (4)	C3B—C4B	1.389 (4)
C3A—H3A	0.93	C3B—H3B	0.93
C4A—C5A	1.379 (6)	C4B—C5B	1.358 (5)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.373 (6)	C5B—C6B	1.365 (6)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.386 (5)	C6B—C7B	1.393 (5)
C6A—H6A	0.93	C6B—H6B	0.93
C7A—H7A	0.93	C7B—H7B	0.93
C8A—C9A	1.465 (4)	C8B—C9B	1.463 (3)
C9A—C10A	1.374 (3)	C9B—C10B	1.371 (3)
C9A—C14A	1.395 (3)	C9B—C14B	1.390 (3)
C10A—C11A	1.369 (4)	C10B—C11B	1.368 (4)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.385 (3)	C11B—C12B	1.368 (4)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.383 (4)	C12B—C13B	1.383 (4)
C13A—C14A	1.355 (4)	C13B—C14B	1.360 (4)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—H14A	0.93	C14B—H14B	0.93
C15A—H15A	0.96	C15B—H15D	0.96
C15A—H15B	0.96	C15B—H15E	0.96
C15A—H15C	0.96	C15B—H15F	0.96
C17A—H17A	0.96	C17B—H17D	0.96
C17A—H17B	0.96	C17B—H17E	0.96
C17A—H17C	0.96	C17B—H17F	0.96
C18A—H18A	0.96	C18B—H18D	0.96
C18A—H18B	0.96	C18B—H18E	0.96
C18A—H18C	0.96	C18B—H18F	0.96
C16A—S1A—C17A	102.89 (13)	C16B—S1B—C17B	102.10 (15)
C16A—S2A—C18A	103.59 (14)	C16B—S2B—C18B	103.01 (14)
C12A—O2A—C15A	117.7 (2)	C12B—O2B—C15B	117.0 (3)
C16A—C1A—C2A	126.2 (2)	C16B—C1B—C2B	126.9 (2)
C16A—C1A—C8A	120.3 (2)	C16B—C1B—C8B	119.3 (2)
C2A—C1A—C8A	113.5 (2)	C2B—C1B—C8B	113.9 (2)
C7A—C2A—C3A	119.2 (3)	C7B—C2B—C3B	118.6 (3)
C7A—C2A—C1A	119.4 (3)	C7B—C2B—C1B	119.2 (3)
C3A—C2A—C1A	121.3 (2)	C3B—C2B—C1B	122.1 (2)
C4A—C3A—C2A	120.6 (3)	C2B—C3B—C4B	120.8 (3)
C4A—C3A—H3A	119.7	C2B—C3B—H3B	119.6
C2A—C3A—H3A	119.7	C4B—C3B—H3B	119.6
C3A—C4A—C5A	119.8 (4)	C5B—C4B—C3B	120.3 (3)
C3A—C4A—H4A	120.1	C5B—C4B—H4B	119.8
C5A—C4A—H4A	120.1	C3B—C4B—H4B	119.8
C6A—C5A—C4A	120.3 (3)	C4B—C5B—C6B	119.4 (3)
C6A—C5A—H5A	119.9	C4B—C5B—H5B	120.3
C4A—C5A—H5A	119.9	C6B—C5B—H5B	120.3
C5A—C6A—C7A	120.1 (4)	C5B—C6B—C7B	121.0 (3)
C5A—C6A—H6A	120.0	C5B—C6B—H6B	119.5
C7A—C6A—H6A	120.0	C7B—C6B—H6B	119.5
C2A—C7A—C6A	120.0 (4)	C2B—C7B—C6B	119.8 (3)
C2A—C7A—H7A	120.0	C2B—C7B—H7B	120.1
C6A—C7A—H7A	120.0	C6B—C7B—H7B	120.1
O1A—C8A—C9A	122.3 (2)	O1B—C8B—C9B	122.4 (2)
O1A—C8A—C1A	120.1 (2)	O1B—C8B—C1B	120.1 (2)
C9A—C8A—C1A	117.5 (2)	C9B—C8B—C1B	117.3 (2)
C10A—C9A—C14A	117.8 (2)	C10B—C9B—C14B	118.2 (2)
C10A—C9A—C8A	122.2 (2)	C10B—C9B—C8B	122.3 (2)
C14A—C9A—C8A	120.0 (2)	C14B—C9B—C8B	119.5 (2)
C11A—C10A—C9A	121.5 (2)	C11B—C10B—C9B	121.3 (2)
C11A—C10A—H10A	119.2	C11B—C10B—H10B	119.4
C9A—C10A—H10A	119.2	C9B—C10B—H10B	119.4
C10A—C11A—C12A	119.8 (2)	C12B—C11B—C10B	119.8 (3)
C10A—C11A—H11A	120.1	C12B—C11B—H11B	120.1
C12A—C11A—H11A	120.1	C10B—C11B—H11B	120.1
O2A—C12A—C13A	116.1 (2)	O2B—C12B—C11B	125.2 (3)
O2A—C12A—C11A	124.5 (2)	O2B—C12B—C13B	114.7 (3)
C13A—C12A—C11A	119.3 (2)	C11B—C12B—C13B	120.1 (2)
C14A—C13A—C12A	120.2 (2)	C14B—C13B—C12B	119.5 (2)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	120.2
C12A—C13A—H13A	119.9	C12B—C13B—H13B	120.2
C13A—C14A—C9A	121.4 (2)	C13B—C14B—C9B	121.1 (2)
C13A—C14A—H14A	119.3	C13B—C14B—H14B	119.4
C9A—C14A—H14A	119.3	C9B—C14B—H14B	119.4
O2A—C15A—H15A	109.5	O2B—C15B—H15D	109.5
O2A—C15A—H15B	109.5	O2B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O2A—C15A—H15C	109.5	O2B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C1A—C16A—S1A	123.45 (19)	C1B—C16B—S1B	122.6 (2)
C1A—C16A—S2A	118.23 (19)	C1B—C16B—S2B	118.5 (2)
S1A—C16A—S2A	118.27 (14)	S1B—C16B—S2B	118.81 (14)
S1A—C17A—H17A	109.5	S1B—C17B—H17D	109.5
S1A—C17A—H17B	109.5	S1B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
S1A—C17A—H17C	109.5	S1B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
S2A—C18A—H18A	109.5	S2B—C18B—H18D	109.5
S2A—C18A—H18B	109.5	S2B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
S2A—C18A—H18C	109.5	S2B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C16A—C1A—C2A—C7A	129.3 (3)	C16B—C1B—C2B—C7B	−131.6 (3)
C8A—C1A—C2A—C7A	−49.8 (3)	C8B—C1B—C2B—C7B	48.8 (3)
C16A—C1A—C2A—C3A	−52.8 (4)	C16B—C1B—C2B—C3B	50.7 (4)
C8A—C1A—C2A—C3A	128.1 (3)	C8B—C1B—C2B—C3B	−128.9 (3)
C7A—C2A—C3A—C4A	−1.7 (4)	C7B—C2B—C3B—C4B	2.1 (4)
C1A—C2A—C3A—C4A	−179.5 (2)	C1B—C2B—C3B—C4B	179.8 (3)
C2A—C3A—C4A—C5A	1.3 (4)	C2B—C3B—C4B—C5B	−0.7 (5)
C3A—C4A—C5A—C6A	−0.5 (5)	C3B—C4B—C5B—C6B	−0.7 (5)
C4A—C5A—C6A—C7A	0.1 (5)	C4B—C5B—C6B—C7B	0.7 (6)
C3A—C2A—C7A—C6A	1.3 (4)	C3B—C2B—C7B—C6B	−2.1 (4)
C1A—C2A—C7A—C6A	179.2 (3)	C1B—C2B—C7B—C6B	−179.9 (3)
C5A—C6A—C7A—C2A	−0.5 (5)	C5B—C6B—C7B—C2B	0.7 (5)
C16A—C1A—C8A—O1A	−92.0 (3)	C16B—C1B—C8B—O1B	90.4 (3)
C2A—C1A—C8A—O1A	87.2 (3)	C2B—C1B—C8B—O1B	−89.9 (3)
C16A—C1A—C8A—C9A	92.1 (3)	C16B—C1B—C8B—C9B	−94.0 (3)
C2A—C1A—C8A—C9A	−88.7 (3)	C2B—C1B—C8B—C9B	85.7 (3)
O1A—C8A—C9A—C10A	175.2 (3)	O1B—C8B—C9B—C10B	−179.3 (3)
C1A—C8A—C9A—C10A	−9.0 (4)	C1B—C8B—C9B—C10B	5.2 (3)
O1A—C8A—C9A—C14A	−4.8 (4)	O1B—C8B—C9B—C14B	2.3 (4)
C1A—C8A—C9A—C14A	171.0 (2)	C1B—C8B—C9B—C14B	−173.2 (2)
C14A—C9A—C10A—C11A	0.1 (4)	C14B—C9B—C10B—C11B	−0.5 (4)
C8A—C9A—C10A—C11A	−179.9 (3)	C8B—C9B—C10B—C11B	−178.9 (2)
C9A—C10A—C11A—C12A	−0.2 (4)	C9B—C10B—C11B—C12B	0.0 (4)
C15A—O2A—C12A—C13A	178.5 (3)	C15B—O2B—C12B—C11B	5.8 (4)
C15A—O2A—C12A—C11A	−2.4 (4)	C15B—O2B—C12B—C13B	−174.3 (3)
C10A—C11A—C12A—O2A	−179.3 (3)	C10B—C11B—C12B—O2B	−179.4 (2)
C10A—C11A—C12A—C13A	−0.2 (4)	C10B—C11B—C12B—C13B	0.7 (4)
O2A—C12A—C13A—C14A	179.8 (2)	O2B—C12B—C13B—C14B	179.2 (2)
C11A—C12A—C13A—C14A	0.7 (4)	C11B—C12B—C13B—C14B	−0.9 (4)
C12A—C13A—C14A—C9A	−0.8 (4)	C12B—C13B—C14B—C9B	0.4 (4)
C10A—C9A—C14A—C13A	0.4 (4)	C10B—C9B—C14B—C13B	0.3 (4)
C8A—C9A—C14A—C13A	−179.6 (2)	C8B—C9B—C14B—C13B	178.7 (2)
C2A—C1A—C16A—S1A	5.3 (4)	C2B—C1B—C16B—S1B	−5.2 (4)
C8A—C1A—C16A—S1A	−175.67 (19)	C8B—C1B—C16B—S1B	174.36 (19)
C2A—C1A—C16A—S2A	−172.2 (2)	C2B—C1B—C16B—S2B	173.0 (2)
C8A—C1A—C16A—S2A	6.8 (3)	C8B—C1B—C16B—S2B	−7.4 (3)
C17A—S1A—C16A—C1A	−125.5 (2)	C17B—S1B—C16B—C1B	125.9 (3)
C17A—S1A—C16A—S2A	52.0 (2)	C17B—S1B—C16B—S2B	−52.4 (2)
C18A—S2A—C16A—C1A	−133.1 (2)	C18B—S2B—C16B—C1B	130.6 (2)
C18A—S2A—C16A—S1A	49.3 (2)	C18B—S2B—C16B—S1B	−51.04 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···S1A	0.93	2.85	3.218 (4)	105
C3B—H3B···S1B	0.93	2.82	3.212 (4)	106
C13A—H13A···Cg1	0.93	2.78	3.701 (3)	171