2,2′-Sulfonyl­bis(2-benzoyl-3-phenyl­oxirane)

The X-ray crystallographic study of the title compound, C₃₀H₂₂O₆S, demonstrates the relative configuration between the aryl and aroyl groups (cis) on one hand, and that between the two oxirane rings (cis) on the other. The crystal packing is characterized by a C—H...O interaction and C...O short contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.084
• wR factor = 0.221
• Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Organic synthesis of small ring heterocycles, such as oxiranes, assume great importance in view of their reactivity towards a host of reagents and the synthetic potential associated with them. Details of chemical synthesis, NMR studies and preliminary crystallographic data for the title compound, (I), have already been reported (Renuga et al., 1999). Interestingly, the (I) exhibits stereoisomerism and the difficulty in ascertaining the configuration arises because one of the C atoms of each oxirane ring is a chiral center, as a result of which the molecule further exhibits diastereoisomerism with respect to the oxirane rings. Recently, the crystal structure of 2.2'-thiobis[2-benzoyl-3-(4-chlorophenyl)oxirane] (Krishnakumar et al., 2002) was elucidated in our laboratory.

Fig. 1 shows the atom-numbering scheme adopted for (I). This study demonstrates the relative configuration between the aryl and aroyl groups (cis) on one hand and that between the two oxirane rings (cis) on the other. 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.

Fig. 2 shows the arrangement of molecules in layers parallel to the (020) plane, viewed down the a axis. The packing features of (I) are distinctly different from those of the 2.2'-thiobis[2-benzoyl-3-(4-chlrophenyl)oxirane], as its packing is determined, not only by the C—H···O, but also by the Cl···Cl interactions. The molecules of (I) do not directly interact among themselves, except for the presence of a C—H···O hydrogen bond. In addition, the structure is stablized by a number of C···O short contacts (see Table 1). Since the molecules of (I) have aromatic rings, C—H···π interactions are expected to play a dominent role in stablizing the crystal packing. An investigation (Malone et al., 1997) on the nature of C—H···π interactions using the Cambridge Structural Database (Allen & Kennard, 1993) and theoretical calculations suggest six possible forms of interactions between an H atom and an aromatic ring. A recent database study (Umezawa et al., 1998) on the nature of C—H···π interactions shows that these interactions also contribute sufficiently to the optimum packing modes observed in the crystal structures of organic compounds. The observed H···π distances are 3.002 and 3.003 Å (below a cut off value of 3.05 Å), with C—H···π angles 158 and 133°.

S2. Experimental

Colourless single crystals of (I) were obtained as transparent needles from a saturated solution in methanol by slow evaporation at room temperature.

S3. Refinement

All H atoms were included in calculated positions with distances of 0.93 (for sp² C—H) and 0.98 Å (for sp³ C—H). In the refinement, they were included as riding, with U_iso values equal to 1.2U_eq of the carrier atom.

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. View of (I), showing the atom-numbering scheme adopted, with the displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram, showing the arrangement of molecules in layers parallel to the (020) plane viewed down the a axis.

2,2'-Sulfonylbis(2-benzoyl-3-phenyloxirane)

Crystal data

C30H22O6S	F(000) = 1064
Mr = 510.54	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.228 (3) Å	θ = 14–27°
b = 11.754 (6) Å	µ = 1.50 mm^−1
c = 18.659 (5) Å	T = 293 K
β = 119.05 (2)°	Needle, colourless
V = 2536.2 (16) Å^3	0.40 × 0.34 × 0.24 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	3365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 69.9°, θmin = 3.8°
ω–2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = −14→0
Tmin = 0.576, Tmax = 0.698	l = −22→19
5012 measured reflections	2 standard reflections every 100 reflections
4795 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.221	w = 1/[σ^2(Fo^2) + 14.8815P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
4795 reflections	Δρmax = 0.43 e Å^−3
335 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00103 (5)

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
S1	0.34843 (13)	0.65913 (13)	0.61230 (9)	0.0489 (4)
O1	0.3329 (3)	0.7980 (4)	0.7185 (3)	0.0511 (10)
O2	0.5153 (4)	0.9143 (4)	0.7170 (3)	0.0610 (12)
O3	0.2596 (4)	0.5918 (4)	0.6147 (3)	0.0655 (13)
O1'	0.3611 (4)	0.8300 (4)	0.5232 (3)	0.0614 (12)
O2'	0.1911 (4)	0.9329 (4)	0.5424 (4)	0.0777 (15)
O3'	0.4373 (4)	0.6069 (4)	0.6007 (3)	0.0643 (13)
C1	0.4169 (4)	0.7422 (5)	0.7050 (3)	0.0414 (13)
C2	0.3932 (5)	0.7034 (5)	0.7715 (4)	0.0451 (13)
H2	0.3484	0.6330	0.7600	0.054*
C3	0.4710 (5)	0.7266 (5)	0.8579 (4)	0.0477 (14)
C4	0.5008 (6)	0.8379 (6)	0.8894 (4)	0.0564 (16)
H4	0.4728	0.9000	0.8541	0.068*
C5	0.5711 (6)	0.8550 (7)	0.9719 (4)	0.0673 (19)
H5	0.5904	0.9287	0.9921	0.081*
C6	0.6135 (6)	0.7645 (8)	1.0253 (4)	0.073 (2)
H6	0.6602	0.7766	1.0812	0.087*
C7	0.5853 (6)	0.6553 (7)	0.9943 (4)	0.070 (2)
H7	0.6144	0.5933	1.0295	0.083*
C8	0.5156 (6)	0.6380 (6)	0.9128 (4)	0.0581 (17)
H8	0.4972	0.5638	0.8934	0.070*
C9	0.5236 (5)	0.8109 (5)	0.7213 (3)	0.0420 (13)
C10	0.6313 (5)	0.7487 (5)	0.7431 (3)	0.0439 (13)
C11	0.7208 (5)	0.8060 (6)	0.7392 (4)	0.0564 (16)
H11	0.7119	0.8819	0.7233	0.068*
C12	0.8221 (6)	0.7499 (8)	0.7592 (5)	0.074 (2)
H12	0.8815	0.7880	0.7561	0.089*
C13	0.8369 (6)	0.6368 (8)	0.7839 (5)	0.075 (2)
H13	0.9061	0.5998	0.7978	0.090*
C14	0.7496 (6)	0.5800 (7)	0.7877 (4)	0.0668 (19)
H14	0.7594	0.5041	0.8038	0.080*
C15	0.6467 (5)	0.6346 (5)	0.7679 (4)	0.0496 (15)
H15	0.5878	0.5957	0.7710	0.060*
C1'	0.2779 (5)	0.7659 (5)	0.5325 (3)	0.0437 (13)
C2'	0.2976 (5)	0.7468 (6)	0.4613 (4)	0.0562 (16)
H2'	0.3405	0.6775	0.4640	0.067*
C3'	0.2155 (6)	0.7870 (7)	0.3774 (4)	0.0643 (19)
C4'	0.1838 (7)	0.8986 (8)	0.3593 (5)	0.085 (3)
H4'	0.2110	0.9532	0.4006	0.102*
C5'	0.1088 (8)	0.9298 (11)	0.2767 (7)	0.109 (4)
H5'	0.0866	1.0052	0.2630	0.131*
C6'	0.0693 (9)	0.8468 (14)	0.2168 (7)	0.121 (5)
H6'	0.0212	0.8671	0.1624	0.145*
C7'	0.0994 (8)	0.7365 (13)	0.2360 (6)	0.110 (4)
H7'	0.0693	0.6812	0.1953	0.132*
C8'	0.1735 (7)	0.7067 (9)	0.3145 (5)	0.084 (3)
H8'	0.1967	0.6313	0.3267	0.101*
C9'	0.1763 (5)	0.8315 (5)	0.5273 (4)	0.0502 (15)
C10'	0.0649 (5)	0.7747 (5)	0.5037 (4)	0.0497 (14)
C11'	−0.0185 (6)	0.8325 (7)	0.5134 (4)	0.0646 (19)
H11'	−0.0026	0.9050	0.5361	0.078*
C12'	−0.1249 (7)	0.7845 (8)	0.4900 (6)	0.086 (3)
H12'	−0.1803	0.8243	0.4970	0.103*
C13'	−0.1489 (6)	0.6763 (8)	0.4557 (5)	0.083 (3)
H13'	−0.2202	0.6426	0.4402	0.099*
C14'	−0.0667 (6)	0.6196 (7)	0.4452 (4)	0.069 (2)
H14'	−0.0833	0.5472	0.4221	0.083*
C15'	0.0398 (5)	0.6670 (6)	0.4679 (4)	0.0567 (16)
H15'	0.0942	0.6277	0.4594	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0419 (8)	0.0425 (8)	0.0499 (8)	−0.0008 (6)	0.0126 (6)	−0.0018 (7)
O1	0.046 (2)	0.055 (3)	0.056 (2)	0.0112 (19)	0.027 (2)	0.003 (2)
O2	0.066 (3)	0.038 (2)	0.083 (3)	−0.002 (2)	0.040 (3)	0.002 (2)
O3	0.055 (3)	0.056 (3)	0.063 (3)	−0.018 (2)	0.011 (2)	0.008 (2)
O1'	0.048 (2)	0.068 (3)	0.067 (3)	−0.008 (2)	0.027 (2)	0.003 (2)
O2'	0.073 (3)	0.045 (3)	0.111 (4)	0.001 (2)	0.041 (3)	−0.010 (3)
O3'	0.059 (3)	0.059 (3)	0.063 (3)	0.020 (2)	0.020 (2)	−0.008 (2)
C1	0.034 (3)	0.039 (3)	0.050 (3)	−0.001 (2)	0.020 (2)	−0.001 (3)
C2	0.040 (3)	0.043 (3)	0.055 (3)	−0.001 (2)	0.025 (3)	0.002 (3)
C3	0.046 (3)	0.058 (4)	0.050 (3)	−0.001 (3)	0.032 (3)	0.005 (3)
C4	0.067 (4)	0.053 (4)	0.057 (4)	−0.002 (3)	0.036 (3)	0.006 (3)
C5	0.078 (5)	0.077 (5)	0.052 (4)	−0.014 (4)	0.036 (4)	−0.009 (4)
C6	0.068 (5)	0.101 (6)	0.047 (4)	−0.004 (4)	0.026 (4)	0.010 (4)
C7	0.074 (5)	0.076 (5)	0.059 (4)	0.014 (4)	0.032 (4)	0.016 (4)
C8	0.065 (4)	0.055 (4)	0.061 (4)	0.008 (3)	0.036 (3)	0.004 (3)
C9	0.044 (3)	0.043 (3)	0.040 (3)	−0.004 (3)	0.021 (3)	0.000 (2)
C10	0.035 (3)	0.053 (3)	0.042 (3)	−0.006 (3)	0.017 (2)	0.003 (3)
C11	0.054 (4)	0.061 (4)	0.061 (4)	−0.012 (3)	0.034 (3)	−0.001 (3)
C12	0.051 (4)	0.092 (6)	0.091 (6)	−0.012 (4)	0.043 (4)	−0.005 (5)
C13	0.045 (4)	0.099 (6)	0.080 (5)	0.015 (4)	0.029 (4)	0.001 (5)
C14	0.055 (4)	0.069 (5)	0.073 (5)	0.014 (4)	0.029 (4)	0.013 (4)
C15	0.044 (3)	0.048 (3)	0.053 (4)	0.003 (3)	0.021 (3)	0.007 (3)
C1'	0.037 (3)	0.045 (3)	0.046 (3)	−0.008 (2)	0.017 (2)	0.000 (3)
C2'	0.045 (3)	0.071 (4)	0.052 (4)	−0.004 (3)	0.023 (3)	−0.004 (3)
C3'	0.050 (4)	0.093 (6)	0.059 (4)	−0.008 (4)	0.035 (3)	0.011 (4)
C4'	0.057 (4)	0.099 (7)	0.088 (6)	−0.015 (4)	0.027 (4)	0.024 (5)
C5'	0.073 (6)	0.131 (9)	0.115 (8)	−0.007 (6)	0.039 (6)	0.060 (8)
C6'	0.075 (7)	0.196 (15)	0.089 (8)	−0.006 (8)	0.038 (6)	0.054 (9)
C7'	0.082 (6)	0.187 (13)	0.065 (6)	−0.008 (8)	0.038 (5)	−0.003 (7)
C8'	0.068 (5)	0.124 (8)	0.061 (5)	0.006 (5)	0.032 (4)	−0.006 (5)
C9'	0.053 (4)	0.040 (3)	0.056 (4)	0.002 (3)	0.026 (3)	−0.005 (3)
C10'	0.041 (3)	0.053 (4)	0.051 (3)	0.006 (3)	0.019 (3)	0.009 (3)
C11'	0.058 (4)	0.066 (5)	0.072 (5)	0.021 (4)	0.033 (4)	0.021 (4)
C12'	0.058 (5)	0.103 (7)	0.112 (7)	0.024 (5)	0.052 (5)	0.036 (6)
C13'	0.042 (4)	0.095 (7)	0.101 (6)	−0.005 (4)	0.026 (4)	0.034 (5)
C14'	0.047 (4)	0.069 (5)	0.073 (5)	−0.007 (3)	0.014 (3)	0.014 (4)
C15'	0.045 (3)	0.053 (4)	0.062 (4)	−0.002 (3)	0.018 (3)	−0.002 (3)

Geometric parameters (Å, º)

S1—O3'	1.432 (4)	C13—C14	1.366 (10)
S1—O3	1.435 (4)	C13—H13	0.9300
S1—C1	1.801 (6)	C14—C15	1.383 (8)
S1—C1'	1.820 (6)	C14—H14	0.9300
O1—C1	1.414 (6)	C15—H15	0.9300
O1—C2	1.443 (7)	C1'—C2'	1.490 (8)
O2—C9	1.220 (7)	C1'—C9'	1.511 (8)
O1'—C1'	1.413 (7)	C2'—C3'	1.484 (9)
O1'—C2'	1.433 (8)	C2'—H2'	0.9800
O2'—C9'	1.218 (7)	C3'—C4'	1.369 (11)
C1—C2	1.490 (8)	C3'—C8'	1.394 (11)
C1—C9	1.523 (7)	C4'—C5'	1.417 (12)
C2—C3	1.457 (8)	C4'—H4'	0.9300
C2—H2	0.9800	C5'—C6'	1.381 (16)
C3—C8	1.376 (9)	C5'—H5'	0.9300
C3—C4	1.410 (9)	C6'—C7'	1.352 (16)
C4—C5	1.374 (9)	C6'—H6'	0.9300
C4—H4	0.9300	C7'—C8'	1.355 (12)
C5—C6	1.376 (10)	C7'—H7'	0.9300
C5—H5	0.9300	C8'—H8'	0.9300
C6—C7	1.383 (11)	C9'—C10'	1.476 (8)
C6—H6	0.9300	C10'—C11'	1.381 (8)
C7—C8	1.357 (9)	C10'—C15'	1.394 (9)
C7—H7	0.9300	C11'—C12'	1.374 (10)
C8—H8	0.9300	C11'—H11'	0.9300
C9—C10	1.472 (8)	C12'—C13'	1.390 (12)
C10—C11	1.393 (8)	C12'—H12'	0.9300
C10—C15	1.401 (8)	C13'—C14'	1.368 (11)
C11—C12	1.373 (10)	C13'—H13'	0.9300
C11—H11	0.9300	C14'—C15'	1.377 (9)
C12—C13	1.389 (11)	C14'—H14'	0.9300
C12—H12	0.9300	C15'—H15'	0.9300
C4···O3'^i	3.25 (1)	C14···O1^iii	3.47 (1)
C5···O3'^i	3.24 (1)	C7'···O1^v	3.29 (1)
C7···O1'^ii	3.27 (1)	C8'···O1^v	3.37 (1)
C8···O2^iii	3.46 (1)	C14'···C12^vi	3.41 (1)
C12···C14'^iv	3.41 (1)
O3'—S1—O3	120.8 (3)	C15—C14—H14	119.8
O3'—S1—C1	108.1 (3)	C14—C15—C10	119.9 (6)
O3—S1—C1	107.9 (3)	C14—C15—H15	120.0
O3'—S1—C1'	107.7 (3)	C10—C15—H15	120.0
O3—S1—C1'	107.7 (3)	O1'—C1'—C2'	59.1 (4)
C1—S1—C1'	103.3 (3)	O1'—C1'—C9'	116.2 (5)
C1—O1—C2	62.9 (3)	C2'—C1'—C9'	123.7 (5)
C1'—O1'—C2'	63.1 (4)	O1'—C1'—S1	110.3 (4)
O1—C1—C2	59.5 (3)	C2'—C1'—S1	112.5 (4)
O1—C1—C9	116.8 (5)	C9'—C1'—S1	119.5 (4)
C2—C1—C9	123.0 (5)	O1'—C2'—C3'	118.3 (6)
O1—C1—S1	110.5 (4)	O1'—C2'—C1'	57.8 (4)
C2—C1—S1	115.0 (4)	C3'—C2'—C1'	122.5 (6)
C9—C1—S1	117.7 (4)	O1'—C2'—H2'	115.3
O1—C2—C3	118.2 (5)	C3'—C2'—H2'	115.3
O1—C2—C1	57.6 (3)	C1'—C2'—H2'	115.3
C3—C2—C1	122.9 (5)	C4'—C3'—C8'	119.5 (8)
O1—C2—H2	115.3	C4'—C3'—C2'	123.0 (8)
C3—C2—H2	115.3	C8'—C3'—C2'	117.4 (8)
C1—C2—H2	115.3	C3'—C4'—C5'	119.0 (10)
C8—C3—C4	117.4 (6)	C3'—C4'—H4'	120.5
C8—C3—C2	120.0 (6)	C5'—C4'—H4'	120.5
C4—C3—C2	122.6 (6)	C6'—C5'—C4'	119.2 (11)
C5—C4—C3	120.2 (6)	C6'—C5'—H5'	120.4
C5—C4—H4	119.9	C4'—C5'—H5'	120.4
C3—C4—H4	119.9	C7'—C6'—C5'	121.0 (11)
C4—C5—C6	121.0 (7)	C7'—C6'—H6'	119.5
C4—C5—H5	119.5	C5'—C6'—H6'	119.5
C6—C5—H5	119.5	C6'—C7'—C8'	120.0 (12)
C5—C6—C7	118.9 (7)	C6'—C7'—H7'	120.0
C5—C6—H6	120.6	C8'—C7'—H7'	120.0
C7—C6—H6	120.6	C7'—C8'—C3'	121.3 (10)
C8—C7—C6	120.4 (7)	C7'—C8'—H8'	119.4
C8—C7—H7	119.8	C3'—C8'—H8'	119.4
C6—C7—H7	119.8	O2'—C9'—C10'	122.5 (6)
C7—C8—C3	122.2 (7)	O2'—C9'—C1'	116.5 (6)
C7—C8—H8	118.9	C10'—C9'—C1'	121.0 (5)
C3—C8—H8	118.9	C11'—C10'—C15'	119.3 (6)
O2—C9—C10	123.9 (5)	C11'—C10'—C9'	118.9 (6)
O2—C9—C1	118.0 (5)	C15'—C10'—C9'	121.7 (6)
C10—C9—C1	118.1 (5)	C12'—C11'—C10'	121.1 (8)
C11—C10—C15	119.3 (6)	C12'—C11'—H11'	119.4
C11—C10—C9	118.6 (6)	C10'—C11'—H11'	119.4
C15—C10—C9	122.1 (5)	C11'—C12'—C13'	119.5 (8)
C12—C11—C10	119.7 (7)	C11'—C12'—H12'	120.3
C12—C11—H11	120.2	C13'—C12'—H12'	120.3
C10—C11—H11	120.2	C14'—C13'—C12'	119.4 (7)
C11—C12—C13	120.8 (7)	C14'—C13'—H13'	120.3
C11—C12—H12	119.6	C12'—C13'—H13'	120.3
C13—C12—H12	119.6	C13'—C14'—C15'	121.7 (8)
C14—C13—C12	119.9 (7)	C13'—C14'—H14'	119.2
C14—C13—H13	120.0	C15'—C14'—H14'	119.2
C12—C13—H13	120.0	C14'—C15'—C10'	119.0 (7)
C13—C14—C15	120.4 (7)	C14'—C15'—H15'	120.5
C13—C14—H14	119.8	C10'—C15'—H15'	120.5
C2—O1—C1—C9	−114.3 (6)	C2'—O1'—C1'—C9'	−115.2 (6)
C2—O1—C1—S1	107.6 (4)	C2'—O1'—C1'—S1	104.7 (5)
O3'—S1—C1—O1	178.7 (4)	O3'—S1—C1'—O1'	−44.1 (5)
O3—S1—C1—O1	−49.2 (4)	O3—S1—C1'—O1'	−175.9 (4)
C1'—S1—C1—O1	64.7 (4)	C1—S1—C1'—O1'	70.1 (4)
O3'—S1—C1—C2	−116.4 (4)	O3'—S1—C1'—C2'	19.9 (5)
O3—S1—C1—C2	15.8 (5)	O3—S1—C1'—C2'	−111.9 (4)
C1'—S1—C1—C2	129.6 (4)	C1—S1—C1'—C2'	134.1 (4)
O3'—S1—C1—C9	41.0 (5)	O3'—S1—C1'—C9'	177.3 (4)
O3—S1—C1—C9	173.1 (4)	O3—S1—C1'—C9'	45.5 (5)
C1'—S1—C1—C9	−73.0 (5)	C1—S1—C1'—C9'	−68.4 (5)
C1—O1—C2—C3	113.0 (6)	C1'—O1'—C2'—C3'	112.4 (6)
C9—C1—C2—O1	104.0 (6)	C9'—C1'—C2'—O1'	102.6 (6)
S1—C1—C2—O1	−100.0 (4)	S1—C1'—C2'—O1'	−101.0 (4)
O1—C1—C2—C3	−104.8 (6)	O1'—C1'—C2'—C3'	−105.3 (7)
C9—C1—C2—C3	−0.8 (9)	C9'—C1'—C2'—C3'	−2.7 (10)
S1—C1—C2—C3	155.2 (5)	S1—C1'—C2'—C3'	153.7 (6)
O1—C2—C3—C8	169.5 (5)	O1'—C2'—C3'—C4'	−10.7 (10)
C1—C2—C3—C8	−122.6 (6)	C1'—C2'—C3'—C4'	57.2 (10)
O1—C2—C3—C4	−8.4 (8)	O1'—C2'—C3'—C8'	166.5 (6)
C1—C2—C3—C4	59.4 (8)	C1'—C2'—C3'—C8'	−125.5 (7)
C8—C3—C4—C5	−0.4 (9)	C8'—C3'—C4'—C5'	0.0 (11)
C2—C3—C4—C5	177.6 (6)	C2'—C3'—C4'—C5'	177.2 (7)
C3—C4—C5—C6	−0.1 (11)	C3'—C4'—C5'—C6'	0.3 (13)
C4—C5—C6—C7	0.8 (11)	C4'—C5'—C6'—C7'	1.1 (16)
C5—C6—C7—C8	−1.1 (12)	C5'—C6'—C7'—C8'	−2.9 (17)
C6—C7—C8—C3	0.6 (11)	C6'—C7'—C8'—C3'	3.2 (14)
C4—C3—C8—C7	0.2 (10)	C4'—C3'—C8'—C7'	−1.8 (12)
C2—C3—C8—C7	−177.8 (6)	C2'—C3'—C8'—C7'	−179.1 (7)
O1—C1—C9—O2	−24.7 (8)	O1'—C1'—C9'—O2'	−23.3 (8)
C2—C1—C9—O2	−94.3 (7)	C2'—C1'—C9'—O2'	−92.2 (8)
S1—C1—C9—O2	110.3 (6)	S1—C1'—C9'—O2'	113.0 (6)
O1—C1—C9—C10	154.0 (5)	O1'—C1'—C9'—C10'	155.8 (5)
C2—C1—C9—C10	84.5 (7)	C2'—C1'—C9'—C10'	86.9 (8)
S1—C1—C9—C10	−70.9 (6)	S1—C1'—C9'—C10'	−67.9 (7)
O2—C9—C10—C11	−16.3 (9)	O2'—C9'—C10'—C11'	−12.2 (10)
C1—C9—C10—C11	165.1 (5)	C1'—C9'—C10'—C11'	168.8 (6)
O2—C9—C10—C15	163.3 (6)	O2'—C9'—C10'—C15'	164.3 (7)
C1—C9—C10—C15	−15.4 (8)	C1'—C9'—C10'—C15'	−14.7 (9)
C15—C10—C11—C12	0.5 (10)	C15'—C10'—C11'—C12'	1.4 (10)
C9—C10—C11—C12	−180.0 (6)	C9'—C10'—C11'—C12'	178.0 (7)
C10—C11—C12—C13	−0.6 (11)	C10'—C11'—C12'—C13'	−0.2 (12)
C11—C12—C13—C14	0.6 (13)	C11'—C12'—C13'—C14'	−0.6 (12)
C12—C13—C14—C15	−0.6 (12)	C12'—C13'—C14'—C15'	0.2 (12)
C13—C14—C15—C10	0.5 (11)	C13'—C14'—C15'—C10'	1.0 (11)
C11—C10—C15—C14	−0.4 (9)	C11'—C10'—C15'—C14'	−1.8 (10)
C9—C10—C15—C14	−179.9 (6)	C9'—C10'—C15'—C14'	−178.3 (6)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) x−1, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2^iii	0.93	2.60	3.458 (8)	154

Symmetry code: (iii) −x+1, y−1/2, −z+3/2.