2,2′-Thio­bis­[2-benzoyl-3-(4-chloro­phenyl)­oxirane]

The X-ray crystallographic study of the title mol­ecule, C₃₀H₂₀Cl₂O₄S, demonstrates the relative configuration between the aryl and aroyl groups (trans) on the one hand, and that between the two oxirane rings (trans) on the other. In the crystal, the molecular packing is stabilized by C—H...O hydrogen bonds and Cl...Cl short contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.116
• Data-to-parameter ratio = 11.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Among heterocycles, small ring systems, such as oxiranes, assume much importance in organic synthesis. These strained heterocycles can undergo facile reaction with a host of nucleophiles affording novel products. Details of chemical synthesis, NMR studies and preliminary crystallographic data of the title compound, (I), have already been reported (Renuga et al., 1999). Interestingly, (I) exhibits stereoisomerism and the difficulty in ascertaining the configuration arises as one of the C atoms of each oxirane ring is quaternary as a result of which the molecule further exhibits diastereoisomerism with respect to the oxirane rings. The present X-ray study reports the complete structural details of (I).

This study points to the relative configuration between the aryl and aroyl groups (trans) on one hand and that between the two oxirane rings (trans) on the other. The molecular packing in the crystal is characterized by C—H···O hydrogen bonds and Cl···Cl short contacts. In the crystal, the molecules are linked by intermolecular C—H···O hydrogen bonds to form an infinite two-dimensional zigzag network parallel to the bc plane. The Cl···Cl short contacts observed in the structure are (a) Cl1···Cl1'ⁱ 3.746 (2) Å and (b) Cl1'···Cl1'ⁱⁱ 3.459 (1) Å [symmetry codes: (i) 1 - x, -y,-z; (ii) -x, -y, -z]. A study on the nature of Cl···Cl interactions on flat rigid molecules with moderately polar substituents (Sarma & Desiraju, 1986) suggests a range of 3.27–4.10 Å for the Cl···Cl short contacts in these group of structures. The value of 3.746 (2) Å in (I) is also significant. This may be due to the flexible nature of the molecule, in spite of being bulky. The configuration of (I) which is symmetrical in solution in the absence of intermolecular interactions, assumes an unsymmetrical configuration in the solid state. The absence of symmetry is probably necessitated by the optimum packing considerations which bring different oxirane molecules in proximity, unlike in solution.

S2. Experimental

Colourless single crystals of the title compound were obtained as transparent needles from its saturated solution in methanol by slow evaporation at room temperature.

S3. Refinement

All the H atoms were located from a difference Fourier map and were included in refinement with isotropic displacement parameters. The C—H distances range from 0.90 (3) to 0.99 (3) Å.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. PLATON (Spek, 1999) diagram with displacement ellipsoids drawn at the 30% probability level showing the numbering scheme adopted.
	Fig. 2. Packing of the molecules of (I) viewed down the a axis.

2,2'-thiobis(2-benzoyl-3-(4-chlorophenyl)oxirane)

Crystal data

C30H20Cl2O4S	F(000) = 1128
Mr = 547.42	Dx = 1.385 Mg m^−3
Monoclinic, P21/c	Melting point: 157(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.0724 (17) Å	Cell parameters from 25 reflections
b = 16.3184 (16) Å	θ = 8–13°
c = 11.768 (3) Å	µ = 0.36 mm^−1
β = 103.66 (2)°	T = 293 K
V = 2626.0 (8) Å^3	Needle, colourless
Z = 4	0.43 × 0.32 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3241 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–2θ scans	h = −16→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.84, Tmax = 0.91	l = 0→13
4835 measured reflections	2 standard reflections every 60 min
4587 independent reflections	intensity decay: <2%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	All H-atom parameters refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.9486P] where P = (Fo^2 + 2Fc^2)/3
4587 reflections	(Δ/σ)max < 0.001
414 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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
Cl1	0.02500 (7)	0.29560 (6)	0.49783 (10)	0.0971 (3)
Cl1'	0.88584 (5)	0.49366 (6)	0.40510 (7)	0.0730 (3)
S1	0.39182 (5)	0.47228 (4)	0.31217 (5)	0.04482 (18)
O1	0.30838 (14)	0.38156 (12)	0.11740 (15)	0.0596 (5)
O1'	0.41833 (13)	0.63302 (11)	0.27413 (15)	0.0518 (5)
O2	0.49349 (17)	0.37525 (17)	0.08187 (17)	0.0884 (8)
O2'	0.29636 (15)	0.56429 (15)	0.01881 (16)	0.0704 (6)
C1	0.39180 (19)	0.38917 (16)	0.2125 (2)	0.0475 (6)
C1'	0.38650 (18)	0.55804 (15)	0.2149 (2)	0.0425 (6)
C2	0.3206 (2)	0.32129 (18)	0.2089 (3)	0.0567 (7)
C2'	0.47509 (19)	0.59922 (16)	0.1974 (2)	0.0478 (6)
C3	0.24644 (19)	0.31651 (16)	0.2791 (3)	0.0537 (7)
C3'	0.57680 (18)	0.57421 (15)	0.2510 (2)	0.0435 (6)
C4	0.1679 (2)	0.36992 (19)	0.2628 (3)	0.0608 (8)
C4'	0.6136 (2)	0.57065 (19)	0.3717 (2)	0.0557 (7)
C5	0.0995 (2)	0.3637 (2)	0.3282 (3)	0.0667 (9)
C5'	0.7076 (2)	0.5472 (2)	0.4186 (2)	0.0595 (8)
C6	0.1095 (2)	0.30344 (18)	0.4118 (3)	0.0625 (8)
C6'	0.76716 (18)	0.52692 (17)	0.3457 (2)	0.0510 (7)
C7	0.1854 (2)	0.2493 (2)	0.4288 (3)	0.0667 (8)
C7'	0.7334 (2)	0.53037 (18)	0.2264 (2)	0.0529 (7)
C8	0.2533 (2)	0.25561 (19)	0.3628 (3)	0.0633 (8)
C8'	0.6386 (2)	0.55418 (17)	0.1798 (2)	0.0504 (7)
C9	0.4877 (2)	0.36998 (17)	0.1821 (2)	0.0531 (7)
C9'	0.2922 (2)	0.56770 (16)	0.1205 (2)	0.0490 (6)
C10	0.57080 (19)	0.34187 (15)	0.2760 (2)	0.0466 (6)
C10'	0.19918 (19)	0.58210 (15)	0.1551 (2)	0.0478 (6)
C11	0.6625 (2)	0.33480 (18)	0.2532 (3)	0.0572 (7)
C11'	0.1120 (2)	0.5799 (2)	0.0693 (3)	0.0639 (8)
C12	0.7402 (2)	0.3049 (2)	0.3366 (4)	0.0742 (10)
C12'	0.0240 (2)	0.5926 (2)	0.0982 (4)	0.0813 (10)
C13	0.7268 (3)	0.2810 (2)	0.4434 (4)	0.0766 (10)
C13'	0.0208 (3)	0.6076 (2)	0.2128 (4)	0.0803 (10)
C14	0.6366 (3)	0.2886 (2)	0.4692 (3)	0.0702 (9)
C14'	0.1063 (2)	0.6108 (2)	0.2972 (3)	0.0701 (9)
C15	0.5582 (2)	0.31847 (18)	0.3858 (2)	0.0553 (7)
C15'	0.1949 (2)	0.59803 (19)	0.2695 (3)	0.0575 (7)
H2	0.3423 (18)	0.2708 (17)	0.188 (2)	0.052 (8)*
H2'	0.4696 (19)	0.6282 (17)	0.129 (2)	0.055 (8)*
H4	0.1621 (19)	0.4090 (18)	0.205 (3)	0.059 (8)*
H4'	0.5691 (19)	0.5840 (16)	0.414 (2)	0.054 (8)*
H5	0.046 (2)	0.401 (2)	0.315 (3)	0.087 (11)*
H5'	0.733 (2)	0.5422 (18)	0.497 (3)	0.066 (9)*
H7	0.190 (2)	0.206 (2)	0.486 (3)	0.079 (10)*
H7'	0.774 (2)	0.5168 (17)	0.181 (2)	0.058 (8)*
H8	0.304 (2)	0.2204 (19)	0.371 (3)	0.074 (10)*
H8'	0.6152 (19)	0.5571 (17)	0.101 (3)	0.058 (8)*
H11	0.669 (2)	0.3501 (17)	0.181 (3)	0.061 (9)*
H11'	0.116 (2)	0.5705 (19)	−0.009 (3)	0.075 (10)*
H12	0.804 (2)	0.301 (2)	0.320 (3)	0.081 (10)*
H12'	−0.034 (3)	0.591 (2)	0.037 (3)	0.099 (12)*
H13	0.782 (2)	0.257 (2)	0.503 (3)	0.083 (10)*
H13'	−0.042 (2)	0.6194 (19)	0.233 (3)	0.079 (10)*
H14	0.627 (2)	0.271 (2)	0.542 (3)	0.084 (11)*
H14'	0.105 (3)	0.617 (2)	0.375 (3)	0.092 (12)*
H15	0.4971 (19)	0.3251 (16)	0.402 (2)	0.050 (8)*
H15'	0.252 (2)	0.5996 (16)	0.330 (2)	0.054 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0980 (7)	0.0851 (6)	0.1232 (9)	0.0002 (5)	0.0562 (6)	0.0049 (6)
Cl1'	0.0505 (4)	0.0934 (6)	0.0690 (5)	0.0062 (4)	0.0021 (4)	0.0037 (4)
S1	0.0546 (4)	0.0477 (4)	0.0313 (3)	0.0023 (3)	0.0083 (3)	−0.0001 (3)
O1	0.0664 (12)	0.0643 (12)	0.0403 (10)	−0.0008 (10)	−0.0032 (9)	−0.0077 (9)
O1'	0.0582 (11)	0.0458 (10)	0.0509 (10)	0.0041 (8)	0.0119 (9)	−0.0080 (9)
O2	0.0930 (16)	0.138 (2)	0.0377 (12)	0.0303 (15)	0.0235 (11)	0.0139 (13)
O2'	0.0709 (13)	0.1043 (17)	0.0332 (10)	0.0112 (12)	0.0066 (9)	−0.0033 (11)
C1	0.0545 (15)	0.0495 (15)	0.0335 (13)	0.0037 (12)	0.0005 (11)	−0.0015 (11)
C1'	0.0511 (14)	0.0420 (13)	0.0323 (12)	0.0049 (11)	0.0057 (11)	−0.0043 (11)
C2	0.0634 (18)	0.0481 (16)	0.0529 (17)	0.0022 (14)	0.0026 (14)	−0.0077 (14)
C2'	0.0578 (16)	0.0477 (15)	0.0373 (14)	0.0018 (12)	0.0097 (12)	0.0029 (12)
C3	0.0504 (15)	0.0435 (15)	0.0615 (18)	−0.0028 (12)	0.0017 (13)	−0.0050 (13)
C3'	0.0465 (14)	0.0448 (14)	0.0378 (13)	−0.0030 (11)	0.0069 (11)	0.0013 (11)
C4	0.0600 (18)	0.0516 (17)	0.0645 (19)	0.0026 (14)	0.0023 (15)	0.0098 (16)
C4'	0.0501 (16)	0.078 (2)	0.0393 (15)	−0.0010 (14)	0.0106 (13)	−0.0081 (14)
C5	0.0533 (17)	0.0571 (19)	0.086 (2)	0.0079 (15)	0.0098 (17)	0.0079 (17)
C5'	0.0552 (17)	0.088 (2)	0.0324 (14)	−0.0046 (15)	0.0039 (13)	−0.0022 (15)
C6	0.0557 (17)	0.0553 (17)	0.075 (2)	−0.0042 (14)	0.0132 (15)	−0.0011 (16)
C6'	0.0454 (14)	0.0564 (16)	0.0475 (15)	−0.0035 (12)	0.0035 (12)	0.0002 (13)
C7	0.0625 (19)	0.0592 (19)	0.074 (2)	−0.0015 (16)	0.0075 (16)	0.0165 (17)
C7'	0.0514 (16)	0.0645 (18)	0.0450 (15)	0.0009 (14)	0.0158 (13)	−0.0005 (14)
C8	0.0500 (16)	0.0474 (17)	0.087 (2)	0.0058 (14)	0.0061 (16)	0.0093 (16)
C8'	0.0607 (17)	0.0585 (17)	0.0313 (14)	−0.0039 (13)	0.0096 (13)	0.0014 (13)
C9	0.0649 (17)	0.0545 (16)	0.0399 (15)	0.0073 (13)	0.0124 (13)	−0.0022 (12)
C9'	0.0590 (16)	0.0465 (15)	0.0387 (15)	0.0060 (12)	0.0056 (12)	0.0014 (12)
C10	0.0566 (15)	0.0392 (14)	0.0429 (14)	0.0022 (11)	0.0098 (12)	−0.0034 (11)
C10'	0.0500 (14)	0.0445 (14)	0.0461 (15)	0.0056 (12)	0.0060 (12)	0.0017 (12)
C11	0.0624 (18)	0.0509 (17)	0.0601 (19)	−0.0011 (14)	0.0182 (16)	−0.0106 (15)
C11'	0.0590 (18)	0.067 (2)	0.0577 (19)	0.0029 (15)	−0.0015 (15)	0.0007 (16)
C12	0.056 (2)	0.064 (2)	0.097 (3)	0.0017 (16)	0.008 (2)	−0.018 (2)
C12'	0.0511 (19)	0.095 (3)	0.089 (3)	0.0068 (18)	−0.0019 (19)	0.002 (2)
C13	0.076 (2)	0.061 (2)	0.077 (2)	0.0135 (17)	−0.012 (2)	−0.0081 (18)
C13'	0.056 (2)	0.085 (2)	0.104 (3)	0.0121 (18)	0.029 (2)	0.011 (2)
C14	0.093 (3)	0.0616 (19)	0.0480 (18)	0.0090 (18)	0.0002 (18)	0.0072 (16)
C14'	0.068 (2)	0.081 (2)	0.066 (2)	0.0151 (17)	0.0255 (18)	0.0086 (18)
C15	0.0652 (19)	0.0544 (17)	0.0451 (16)	0.0092 (14)	0.0107 (14)	0.0035 (13)
C15'	0.0567 (17)	0.0641 (18)	0.0504 (17)	0.0102 (14)	0.0103 (14)	0.0003 (14)

Geometric parameters (Å, º)

Cl1—C6	1.738 (3)	C6'—C7'	1.374 (4)
Cl1'—C6'	1.738 (3)	C7—C8	1.370 (5)
S1—C1	1.793 (3)	C7—H7	0.96 (3)
S1—C1'	1.798 (3)	C7'—C8'	1.373 (4)
O1—C1	1.423 (3)	C7'—H7'	0.90 (3)
O1—C2	1.438 (3)	C8—H8	0.90 (3)
O1'—C1'	1.427 (3)	C8'—H8'	0.91 (3)
O1'—C2'	1.449 (3)	C9—C10	1.479 (4)
O2—C9	1.205 (3)	C9'—C10'	1.479 (4)
O2'—C9'	1.213 (3)	C10—C11	1.383 (4)
C1—C2	1.488 (4)	C10—C15	1.398 (4)
C1—C9	1.509 (4)	C10'—C15'	1.387 (4)
C1'—C2'	1.473 (4)	C10'—C11'	1.393 (4)
C1'—C9'	1.525 (3)	C11—C12	1.375 (5)
C2—C3	1.478 (4)	C11—H11	0.91 (3)
C2—H2	0.93 (3)	C11'—C12'	1.375 (5)
C2'—C3'	1.479 (4)	C11'—H11'	0.95 (3)
C2'—H2'	0.92 (3)	C12—C13	1.372 (5)
C3—C4	1.385 (4)	C12—H12	0.97 (3)
C3—C8	1.386 (4)	C12'—C13'	1.382 (5)
C3'—C8'	1.381 (4)	C12'—H12'	0.95 (4)
C3'—C4'	1.393 (4)	C13—C14	1.378 (5)
C4—C5	1.371 (5)	C13—H13	0.99 (3)
C4—H4	0.92 (3)	C13'—C14'	1.369 (5)
C4'—C5'	1.363 (4)	C13'—H13'	0.98 (3)
C4'—H4'	0.91 (3)	C14—C15	1.381 (4)
C5—C6	1.375 (4)	C14—H14	0.94 (3)
C5—H5	0.96 (3)	C14'—C15'	1.376 (4)
C5'—C6'	1.373 (4)	C14'—H14'	0.93 (4)
C5'—H5'	0.91 (3)	C15—H15	0.93 (3)
C6—C7	1.365 (4)	C15'—H15'	0.94 (3)
C1—S1—C1'	100.30 (11)	C8—C7—H7	120.5 (19)
C1—O1—C2	62.65 (17)	C8'—C7'—C6'	119.3 (3)
C1'—O1'—C2'	61.63 (16)	C8'—C7'—H7'	121.5 (18)
O1—C1—C2	59.18 (17)	C6'—C7'—H7'	119.2 (18)
O1—C1—C9	114.4 (2)	C7—C8—C3	121.1 (3)
C2—C1—C9	118.2 (2)	C7—C8—H8	122 (2)
O1—C1—S1	116.94 (18)	C3—C8—H8	117 (2)
C2—C1—S1	118.5 (2)	C7'—C8'—C3'	121.1 (3)
C9—C1—S1	116.75 (19)	C7'—C8'—H8'	120.4 (17)
O1'—C1'—C2'	59.92 (16)	C3'—C8'—H8'	118.6 (17)
O1'—C1'—C9'	112.72 (19)	O2—C9—C10	122.0 (3)
C2'—C1'—C9'	118.1 (2)	O2—C9—C1	119.2 (2)
O1'—C1'—S1	113.31 (16)	C10—C9—C1	118.8 (2)
C2'—C1'—S1	122.33 (18)	O2'—C9'—C10'	122.1 (2)
C9'—C1'—S1	116.27 (18)	O2'—C9'—C1'	118.5 (2)
O1—C2—C3	118.6 (2)	C10'—C9'—C1'	119.4 (2)
O1—C2—C1	58.17 (16)	C11—C10—C15	118.9 (3)
C3—C2—C1	125.7 (3)	C11—C10—C9	119.3 (3)
O1—C2—H2	113.4 (17)	C15—C10—C9	121.6 (2)
C3—C2—H2	114.8 (16)	C15'—C10'—C11'	118.4 (3)
C1—C2—H2	113.9 (16)	C15'—C10'—C9'	122.8 (2)
O1'—C2'—C1'	58.45 (15)	C11'—C10'—C9'	118.8 (3)
O1'—C2'—C3'	117.4 (2)	C12—C11—C10	120.8 (3)
C1'—C2'—C3'	125.5 (2)	C12—C11—H11	121.9 (18)
O1'—C2'—H2'	113.9 (17)	C10—C11—H11	117.2 (18)
C1'—C2'—H2'	117.2 (16)	C12'—C11'—C10'	120.5 (3)
C3'—C2'—H2'	112.8 (16)	C12'—C11'—H11'	122.2 (19)
C4—C3—C8	118.0 (3)	C10'—C11'—H11'	117.2 (19)
C4—C3—C2	122.3 (3)	C13—C12—C11	119.8 (3)
C8—C3—C2	119.7 (3)	C13—C12—H12	120 (2)
C8'—C3'—C4'	118.2 (2)	C11—C12—H12	120 (2)
C8'—C3'—C2'	119.4 (2)	C11'—C12'—C13'	120.4 (3)
C4'—C3'—C2'	122.4 (2)	C11'—C12'—H12'	118 (2)
C5—C4—C3	121.2 (3)	C13'—C12'—H12'	121 (2)
C5—C4—H4	120.9 (17)	C12—C13—C14	120.6 (3)
C3—C4—H4	117.9 (18)	C12—C13—H13	120.1 (19)
C5'—C4'—C3'	121.1 (3)	C14—C13—H13	119.3 (19)
C5'—C4'—H4'	125.0 (17)	C14'—C13'—C12'	119.3 (3)
C3'—C4'—H4'	113.9 (17)	C14'—C13'—H13'	120.3 (19)
C4—C5—C6	119.3 (3)	C12'—C13'—H13'	120.3 (19)
C4—C5—H5	120 (2)	C13—C14—C15	119.9 (3)
C6—C5—H5	121 (2)	C13—C14—H14	120 (2)
C4'—C5'—C6'	119.5 (3)	C15—C14—H14	120 (2)
C4'—C5'—H5'	122.7 (18)	C13'—C14'—C15'	120.9 (3)
C6'—C5'—H5'	117.8 (18)	C13'—C14'—H14'	120 (2)
C7—C6—C5	120.8 (3)	C15'—C14'—H14'	119 (2)
C7—C6—Cl1	119.1 (3)	C14—C15—C10	119.9 (3)
C5—C6—Cl1	120.1 (2)	C14—C15—H15	121.4 (16)
C5'—C6'—C7'	120.9 (3)	C10—C15—H15	118.6 (16)
C5'—C6'—Cl1'	119.6 (2)	C14'—C15'—C10'	120.5 (3)
C7'—C6'—Cl1'	119.4 (2)	C14'—C15'—H15'	118.2 (17)
C6—C7—C8	119.6 (3)	C10'—C15'—H15'	121.2 (17)
C6—C7—H7	119.8 (19)
C2—O1—C1—C9	109.5 (3)	Cl1'—C6'—C7'—C8'	177.9 (2)
C2—O1—C1—S1	−108.7 (2)	C6—C7—C8—C3	0.3 (5)
C1'—S1—C1—O1	−61.7 (2)	C4—C3—C8—C7	−1.1 (5)
C1'—S1—C1—C2	−129.5 (2)	C2—C3—C8—C7	−179.7 (3)
C1'—S1—C1—C9	79.2 (2)	C6'—C7'—C8'—C3'	−0.4 (4)
C2'—O1'—C1'—C9'	−110.3 (2)	C4'—C3'—C8'—C7'	0.8 (4)
C2'—O1'—C1'—S1	115.0 (2)	C2'—C3'—C8'—C7'	−179.7 (3)
C1—S1—C1'—O1'	−159.95 (17)	O1—C1—C9—O2	22.9 (4)
C1—S1—C1'—C2'	−91.9 (2)	C2—C1—C9—O2	89.6 (3)
C1—S1—C1'—C9'	67.1 (2)	S1—C1—C9—O2	−119.0 (3)
C1—O1—C2—C3	116.3 (3)	O1—C1—C9—C10	−154.6 (2)
C9—C1—C2—O1	−103.1 (2)	C2—C1—C9—C10	−87.8 (3)
S1—C1—C2—O1	106.0 (2)	S1—C1—C9—C10	63.5 (3)
O1—C1—C2—C3	−104.4 (3)	O1'—C1'—C9'—O2'	108.2 (3)
C9—C1—C2—C3	152.5 (3)	C2'—C1'—C9'—O2'	41.4 (4)
S1—C1—C2—C3	1.6 (4)	S1—C1'—C9'—O2'	−118.5 (3)
C1'—O1'—C2'—C3'	−116.7 (3)	O1'—C1'—C9'—C10'	−70.8 (3)
C9'—C1'—C2'—O1'	101.4 (2)	C2'—C1'—C9'—C10'	−137.7 (2)
S1—C1'—C2'—O1'	−100.1 (2)	S1—C1'—C9'—C10'	62.4 (3)
O1'—C1'—C2'—C3'	103.0 (3)	O2—C9—C10—C11	11.3 (4)
C9'—C1'—C2'—C3'	−155.6 (2)	C1—C9—C10—C11	−171.2 (2)
S1—C1'—C2'—C3'	3.0 (4)	O2—C9—C10—C15	−165.6 (3)
O1—C2—C3—C4	−2.5 (4)	C1—C9—C10—C15	11.9 (4)
C1—C2—C3—C4	67.1 (4)	O2'—C9'—C10'—C15'	−170.3 (3)
O1—C2—C3—C8	175.9 (3)	C1'—C9'—C10'—C15'	8.7 (4)
C1—C2—C3—C8	−114.4 (3)	O2'—C9'—C10'—C11'	9.4 (4)
O1'—C2'—C3'—C8'	−169.6 (2)	C1'—C9'—C10'—C11'	−171.5 (2)
C1'—C2'—C3'—C8'	121.1 (3)	C15—C10—C11—C12	0.3 (4)
O1'—C2'—C3'—C4'	9.8 (4)	C9—C10—C11—C12	−176.7 (3)
C1'—C2'—C3'—C4'	−59.4 (4)	C15'—C10'—C11'—C12'	−0.6 (5)
C8—C3—C4—C5	0.9 (4)	C9'—C10'—C11'—C12'	179.7 (3)
C2—C3—C4—C5	179.3 (3)	C10—C11—C12—C13	0.6 (5)
C8'—C3'—C4'—C5'	−0.7 (4)	C10'—C11'—C12'—C13'	0.0 (6)
C2'—C3'—C4'—C5'	179.8 (3)	C11—C12—C13—C14	−1.7 (5)
C3—C4—C5—C6	0.2 (5)	C11'—C12'—C13'—C14'	0.8 (6)
C3'—C4'—C5'—C6'	0.2 (5)	C12—C13—C14—C15	1.9 (5)
C4—C5—C6—C7	−1.0 (5)	C12'—C13'—C14'—C15'	−1.0 (6)
C4—C5—C6—Cl1	178.8 (2)	C13—C14—C15—C10	−0.9 (5)
C4'—C5'—C6'—C7'	0.3 (5)	C11—C10—C15—C14	−0.2 (4)
C4'—C5'—C6'—Cl1'	−177.9 (2)	C9—C10—C15—C14	176.7 (3)
C5—C6—C7—C8	0.8 (5)	C13'—C14'—C15'—C10'	0.4 (5)
Cl1—C6—C7—C8	−179.0 (3)	C11'—C10'—C15'—C14'	0.4 (4)
C5'—C6'—C7'—C8'	−0.2 (4)	C9'—C10'—C15'—C14'	−179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.97 (3)	2.45 (3)	3.266 (4)	142 (2)
C8′—H8′···O2^ii	0.91 (3)	2.58 (3)	3.400 (3)	151 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z.