Naphthalene-2,3-diylbis[(2-thien-yl)methanone].

The asymmetric unit of the title compound, C(20)H(12)O(2)S(2), contains two crystallographically independent mol-ecules which differ in the orientations of thienylmethanone units with respect to the naphthalene ring system [dihedral angles of 65.30 (11) and 50.94 (11)° in one molecule, 41.94 (12) and 69.61 (13)° in the other]. The crystal structure is stabilized by C-H⋯O and C-H⋯π inter-actions.

Related literature

For a related structure, see: Labat & Halfpenny (2005 ▶). For general background, see: Pellis & West (1968 ▶); Cohen et al. (1977 ▶); Csaszar & Morvay (1983 ▶); Lakshmi et al. (1985 ▶); EI-Maghraby et al. (1984 ▶); Dzhurayev et al. (1992 ▶); Gewald et al. (1996 ▶); Jones et al. (1984 ▶); Palani et al. (2006 ▶).

Experimental

Crystal data

C20H12O2S2

M = 348.42

Monoclinic,

a = 9.7638 (3) Å

b = 11.1418 (4) Å

c = 15.4496 (6) Å

β = 90.266 (1)°

V = 1680.69 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 (2) K

0.21 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.800, T max = 0.950

21289 measured reflections

8580 independent reflections

6591 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.01

8580 reflections

433 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 3970 Friedel pairs

Flack parameter: 0.02 (5)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038701/ci2690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038701/ci2690Isup2.hkl

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

C20H12O2S2	F000 = 720
Mr = 348.42	Dx = 1.377 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8580 reflections
a = 9.7638 (3) Å	θ = 1.3–28.9º
b = 11.1418 (4) Å	µ = 0.33 mm−1
c = 15.4496 (6) Å	T = 293 (2) K
β = 90.266 (1)º	Block, colourless
V = 1680.69 (10) Å3	0.21 × 0.19 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	8580 independent reflections
Radiation source: fine-focus sealed tube	6591 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 293(2) K	θmax = 28.9º
ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.800, Tmax = 0.950	k = −15→14
21289 measured reflections	l = −20→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.3545P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.44 e Å−3
8580 reflections	Δρmin = −0.32 e Å−3
433 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 3970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (5)
Secondary atom site location: difference Fourier map

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
S1	0.06339 (8)	−0.02637 (6)	0.45118 (6)	0.0657 (2)
S2	0.33739 (8)	0.44467 (8)	0.69777 (5)	0.0644 (2)
O1	0.0949 (2)	0.24092 (19)	0.44816 (17)	0.0822 (7)
O2	0.3446 (3)	0.24071 (18)	0.57466 (14)	0.0815 (7)
C1	0.4852 (3)	0.3351 (2)	0.18008 (17)	0.0542 (6)
H1	0.4468	0.2785	0.1429	0.065*
C2	0.5757 (3)	0.4164 (3)	0.14849 (18)	0.0609 (7)
H2	0.5984	0.4148	0.0901	0.073*
C3	0.6350 (3)	0.5021 (3)	0.20256 (18)	0.0571 (6)
H3	0.6966	0.5574	0.1800	0.069*
C4	0.6032 (2)	0.5053 (2)	0.28836 (17)	0.0488 (6)
H4	0.6430	0.5631	0.3239	0.059*
C5	0.5102 (2)	0.42129 (19)	0.32380 (15)	0.0398 (5)
C6	0.4485 (2)	0.3350 (2)	0.26773 (16)	0.0421 (5)
C7	0.3516 (2)	0.2545 (2)	0.30259 (16)	0.0451 (5)
H7	0.3127	0.1966	0.2668	0.054*
C8	0.3135 (2)	0.25942 (19)	0.38716 (16)	0.0434 (5)
C9	0.3768 (2)	0.3442 (2)	0.44373 (16)	0.0442 (5)
C10	0.4727 (2)	0.4227 (2)	0.41136 (15)	0.0428 (5)
H10	0.5137	0.4779	0.4484	0.051*
C11	0.1943 (3)	0.1879 (2)	0.42024 (19)	0.0508 (6)
C12	0.2010 (2)	0.0578 (2)	0.41656 (16)	0.0448 (5)
C13	0.3071 (2)	−0.0134 (2)	0.39437 (17)	0.0484 (6)
H13	0.3903	0.0156	0.3741	0.058*
C14	0.2781 (3)	−0.1368 (2)	0.4053 (2)	0.0608 (7)
H14	0.3397	−0.1980	0.3929	0.073*
C15	0.1515 (3)	−0.1553 (3)	0.4355 (2)	0.0653 (8)
H15	0.1158	−0.2310	0.4467	0.078*
C16	0.3484 (3)	0.3376 (2)	0.53847 (17)	0.0506 (6)
C17	0.3315 (2)	0.4492 (2)	0.58672 (15)	0.0456 (5)
C18	0.3095 (3)	0.5646 (2)	0.55646 (19)	0.0521 (6)
H18	0.3026	0.5854	0.4983	0.062*
C19	0.2991 (3)	0.6466 (3)	0.6262 (2)	0.0696 (8)
H19	0.2841	0.7284	0.6186	0.084*
C20	0.3127 (3)	0.5957 (3)	0.7037 (2)	0.0722 (9)
H20	0.3091	0.6381	0.7555	0.087*
S1'	0.36488 (7)	0.50071 (8)	0.93775 (5)	0.0670 (2)
S2'	1.03585 (9)	0.72925 (8)	0.94344 (7)	0.0795 (3)
O1'	0.6344 (2)	0.55500 (17)	0.87437 (16)	0.0701 (6)
O2'	0.8753 (3)	0.5098 (2)	0.99329 (14)	0.0745 (6)
C1'	0.7926 (3)	0.0907 (2)	0.7211 (2)	0.0694 (9)
H1'	0.7053	0.0575	0.7197	0.083*
C2'	0.8959 (4)	0.0362 (2)	0.6773 (2)	0.0730 (9)
H2'	0.8777	−0.0319	0.6445	0.088*
C3'	1.0280 (3)	0.0812 (2)	0.6812 (2)	0.0677 (8)
H3'	1.0981	0.0421	0.6521	0.081*
C4'	1.0559 (3)	0.1833 (2)	0.7278 (2)	0.0597 (7)
H4'	1.1449	0.2130	0.7300	0.072*
C5'	0.9510 (3)	0.2433 (2)	0.77216 (17)	0.0469 (6)
C6'	0.8160 (3)	0.1970 (2)	0.76870 (18)	0.0498 (6)
C7'	0.7096 (3)	0.2617 (2)	0.80915 (18)	0.0526 (6)
H7'	0.6207	0.2320	0.8061	0.063*
C8'	0.7328 (2)	0.3666 (2)	0.85265 (17)	0.0450 (5)
C9'	0.8698 (2)	0.40998 (19)	0.85839 (16)	0.0433 (5)
C10'	0.9736 (3)	0.3506 (2)	0.81877 (18)	0.0491 (6)
H10'	1.0620	0.3814	0.8224	0.059*
C11'	0.6203 (3)	0.4464 (2)	0.88117 (17)	0.0490 (6)
C12'	0.4927 (3)	0.3989 (2)	0.91630 (17)	0.0484 (6)
C13'	0.4546 (3)	0.2823 (3)	0.93971 (18)	0.0561 (7)
H13'	0.5098	0.2148	0.9340	0.067*
C14'	0.3192 (3)	0.2820 (3)	0.9735 (2)	0.0713 (9)
H14'	0.2752	0.2126	0.9921	0.086*
C15'	0.2605 (3)	0.3915 (3)	0.9763 (2)	0.0723 (9)
H15'	0.1727	0.4056	0.9970	0.087*
C16'	0.9038 (3)	0.5142 (2)	0.91669 (18)	0.0495 (6)
C17'	0.9723 (2)	0.6167 (2)	0.87875 (19)	0.0511 (6)
C18'	0.9843 (3)	0.6463 (2)	0.7926 (2)	0.0577 (7)
H18'	0.9581	0.5964	0.7472	0.069*
C19'	1.0413 (4)	0.7619 (3)	0.7816 (3)	0.0902 (12)
H19'	1.0548	0.7975	0.7278	0.108*
C20'	1.0736 (4)	0.8144 (3)	0.8562 (3)	0.0952 (14)
H20'	1.1130	0.8902	0.8600	0.114*

	U11	U22	U33	U12	U13	U23
S1	0.0555 (4)	0.0583 (4)	0.0835 (5)	−0.0129 (3)	0.0201 (4)	−0.0068 (4)
S2	0.0706 (5)	0.0755 (5)	0.0471 (4)	−0.0149 (4)	0.0070 (3)	−0.0040 (4)
O1	0.0665 (13)	0.0542 (12)	0.126 (2)	0.0072 (10)	0.0366 (13)	−0.0069 (13)
O2	0.135 (2)	0.0491 (11)	0.0603 (13)	0.0066 (12)	0.0098 (13)	0.0124 (10)
C1	0.0642 (17)	0.0556 (15)	0.0428 (15)	−0.0048 (12)	−0.0067 (12)	−0.0048 (12)
C2	0.0709 (19)	0.0683 (18)	0.0437 (15)	−0.0089 (15)	0.0013 (14)	0.0006 (13)
C3	0.0580 (15)	0.0573 (15)	0.0562 (16)	−0.0080 (13)	0.0039 (13)	0.0054 (13)
C4	0.0466 (13)	0.0469 (12)	0.0527 (15)	−0.0022 (11)	−0.0047 (11)	−0.0053 (11)
C5	0.0392 (11)	0.0353 (10)	0.0448 (13)	0.0058 (9)	−0.0047 (10)	−0.0025 (9)
C6	0.0440 (12)	0.0368 (10)	0.0455 (14)	0.0039 (9)	−0.0051 (10)	−0.0031 (9)
C7	0.0466 (13)	0.0396 (11)	0.0491 (15)	−0.0017 (9)	−0.0061 (11)	−0.0072 (10)
C8	0.0438 (12)	0.0333 (10)	0.0530 (15)	0.0032 (9)	−0.0011 (11)	−0.0019 (10)
C9	0.0478 (13)	0.0389 (11)	0.0460 (14)	0.0070 (10)	−0.0008 (11)	−0.0008 (10)
C10	0.0462 (12)	0.0382 (11)	0.0439 (13)	0.0019 (9)	−0.0068 (10)	−0.0060 (10)
C11	0.0481 (14)	0.0435 (12)	0.0610 (17)	0.0015 (10)	0.0054 (12)	−0.0060 (11)
C12	0.0433 (13)	0.0437 (11)	0.0474 (14)	−0.0074 (10)	−0.0008 (11)	−0.0020 (10)
C13	0.0421 (12)	0.0449 (12)	0.0582 (16)	−0.0006 (10)	−0.0013 (11)	0.0002 (11)
C14	0.0656 (18)	0.0427 (13)	0.074 (2)	−0.0007 (12)	−0.0019 (15)	−0.0039 (13)
C15	0.074 (2)	0.0439 (13)	0.078 (2)	−0.0143 (13)	0.0014 (16)	−0.0052 (14)
C16	0.0563 (15)	0.0479 (13)	0.0477 (15)	−0.0002 (11)	0.0008 (12)	0.0014 (11)
C17	0.0433 (12)	0.0505 (13)	0.0429 (13)	−0.0061 (10)	0.0021 (10)	−0.0061 (11)
C18	0.0522 (15)	0.0505 (13)	0.0536 (16)	−0.0017 (11)	0.0036 (12)	−0.0111 (12)
C19	0.082 (2)	0.0509 (15)	0.076 (2)	−0.0088 (14)	0.0077 (17)	−0.0145 (15)
C20	0.085 (2)	0.0714 (19)	0.061 (2)	−0.0177 (17)	0.0105 (17)	−0.0213 (16)
S1'	0.0518 (4)	0.0751 (5)	0.0741 (5)	0.0064 (4)	0.0049 (3)	0.0109 (4)
S2'	0.0642 (5)	0.0705 (5)	0.1039 (7)	−0.0178 (4)	0.0145 (4)	−0.0433 (5)
O1'	0.0608 (12)	0.0444 (10)	0.1051 (18)	0.0024 (8)	0.0171 (12)	0.0143 (10)
O2'	0.1087 (17)	0.0605 (11)	0.0544 (13)	−0.0031 (12)	0.0069 (12)	−0.0051 (10)
C1'	0.0614 (17)	0.0451 (14)	0.102 (3)	−0.0143 (13)	−0.0104 (17)	−0.0143 (15)
C2'	0.077 (2)	0.0430 (15)	0.099 (3)	−0.0012 (13)	−0.0106 (18)	−0.0220 (15)
C3'	0.0627 (18)	0.0486 (15)	0.092 (2)	0.0101 (13)	−0.0075 (16)	−0.0179 (15)
C4'	0.0483 (14)	0.0480 (14)	0.083 (2)	0.0035 (11)	−0.0085 (14)	−0.0124 (14)
C5'	0.0477 (13)	0.0370 (11)	0.0559 (15)	−0.0005 (10)	−0.0089 (11)	−0.0013 (11)
C6'	0.0494 (13)	0.0375 (11)	0.0624 (16)	−0.0048 (10)	−0.0072 (12)	−0.0010 (11)
C7'	0.0459 (14)	0.0474 (13)	0.0645 (17)	−0.0124 (11)	−0.0019 (12)	0.0012 (12)
C8'	0.0424 (12)	0.0398 (12)	0.0528 (15)	−0.0050 (9)	−0.0026 (11)	0.0064 (10)
C9'	0.0453 (13)	0.0356 (11)	0.0489 (14)	−0.0034 (9)	−0.0055 (11)	0.0015 (9)
C10'	0.0417 (13)	0.0427 (12)	0.0629 (17)	−0.0068 (10)	−0.0077 (12)	−0.0056 (12)
C11'	0.0474 (13)	0.0449 (12)	0.0547 (15)	−0.0022 (10)	−0.0015 (11)	0.0052 (11)
C12'	0.0455 (13)	0.0548 (13)	0.0447 (14)	−0.0021 (10)	−0.0032 (11)	0.0053 (11)
C13'	0.0575 (16)	0.0607 (15)	0.0502 (16)	−0.0155 (12)	0.0022 (13)	0.0066 (13)
C14'	0.0674 (19)	0.080 (2)	0.067 (2)	−0.0244 (17)	0.0051 (16)	0.0108 (17)
C15'	0.0505 (16)	0.097 (2)	0.070 (2)	−0.0097 (16)	0.0056 (15)	0.0123 (18)
C16'	0.0467 (13)	0.0436 (12)	0.0580 (17)	0.0035 (10)	−0.0070 (12)	−0.0038 (12)
C17'	0.0399 (13)	0.0418 (11)	0.0717 (18)	−0.0020 (10)	0.0014 (12)	−0.0172 (12)
C18'	0.0589 (16)	0.0415 (13)	0.073 (2)	−0.0023 (11)	0.0052 (14)	−0.0020 (12)
C19'	0.102 (3)	0.0523 (18)	0.116 (3)	−0.0066 (17)	0.041 (2)	0.0019 (19)
C20'	0.080 (2)	0.0568 (18)	0.150 (4)	−0.0257 (17)	0.051 (2)	−0.027 (2)

S1—C15	1.692 (3)	S1'—C15'	1.697 (3)
S1—C12	1.726 (2)	S1'—C12'	1.720 (3)
S2—C20	1.702 (4)	S2'—C20'	1.690 (4)
S2—C17	1.717 (2)	S2'—C17'	1.718 (2)
O1—C11	1.216 (3)	O1'—C11'	1.222 (3)
O2—C16	1.216 (3)	O2'—C16'	1.218 (3)
C1—C2	1.358 (4)	C1'—C2'	1.361 (5)
C1—C6	1.402 (4)	C1'—C6'	1.412 (4)
C1—H1	0.93	C1'—H1'	0.93
C2—C3	1.393 (4)	C2'—C3'	1.384 (4)
C2—H2	0.93	C2'—H2'	0.93
C3—C4	1.363 (4)	C3'—C4'	1.373 (4)
C3—H3	0.93	C3'—H3'	0.93
C4—C5	1.416 (3)	C4'—C5'	1.404 (4)
C4—H4	0.93	C4'—H4'	0.93
C5—C10	1.403 (3)	C5'—C10'	1.413 (3)
C5—C6	1.426 (3)	C5'—C6'	1.416 (3)
C6—C7	1.412 (3)	C6'—C7'	1.412 (4)
C7—C8	1.361 (4)	C7'—C8'	1.366 (3)
C7—H7	0.93	C7'—H7'	0.93
C8—C9	1.425 (3)	C8'—C9'	1.424 (3)
C8—C11	1.503 (4)	C8'—C11'	1.482 (4)
C9—C10	1.377 (3)	C9'—C10'	1.359 (4)
C9—C16	1.493 (4)	C9'—C16'	1.506 (3)
C10—H10	0.93	C10'—H10'	0.93
C11—C12	1.452 (3)	C11'—C12'	1.461 (4)
C12—C13	1.350 (3)	C12'—C13'	1.398 (4)
C13—C14	1.414 (4)	C13'—C14'	1.424 (4)
C13—H13	0.93	C13'—H13'	0.93
C14—C15	1.339 (4)	C14'—C15'	1.348 (5)
C14—H14	0.93	C14'—H14'	0.93
C15—H15	0.93	C15'—H15'	0.93
C16—C17	1.459 (4)	C16'—C17'	1.448 (4)
C17—C18	1.385 (4)	C17'—C18'	1.377 (4)
C18—C19	1.418 (4)	C18'—C19'	1.414 (4)
C18—H18	0.93	C18'—H18'	0.93
C19—C20	1.330 (5)	C19'—C20'	1.329 (6)
C19—H19	0.93	C19'—H19'	0.93
C20—H20	0.93	C20'—H20'	0.93
C15—S1—C12	91.10 (14)	C15'—S1'—C12'	91.82 (16)
C20—S2—C17	91.19 (15)	C20'—S2'—C17'	91.46 (17)
C2—C1—C6	121.1 (2)	C2'—C1'—C6'	121.0 (3)
C2—C1—H1	119.4	C2'—C1'—H1'	119.5
C6—C1—H1	119.4	C6'—C1'—H1'	119.5
C1—C2—C3	120.7 (3)	C1'—C2'—C3'	120.6 (3)
C1—C2—H2	119.6	C1'—C2'—H2'	119.7
C3—C2—H2	119.6	C3'—C2'—H2'	119.7
C4—C3—C2	120.4 (3)	C4'—C3'—C2'	120.4 (3)
C4—C3—H3	119.8	C4'—C3'—H3'	119.8
C2—C3—H3	119.8	C2'—C3'—H3'	119.8
C3—C4—C5	120.5 (2)	C3'—C4'—C5'	120.4 (3)
C3—C4—H4	119.7	C3'—C4'—H4'	119.8
C5—C4—H4	119.7	C5'—C4'—H4'	119.8
C10—C5—C4	122.4 (2)	C4'—C5'—C10'	122.6 (2)
C10—C5—C6	118.8 (2)	C4'—C5'—C6'	119.3 (2)
C4—C5—C6	118.7 (2)	C10'—C5'—C6'	118.1 (2)
C1—C6—C7	122.9 (2)	C1'—C6'—C7'	122.8 (2)
C1—C6—C5	118.5 (2)	C1'—C6'—C5'	118.2 (3)
C7—C6—C5	118.6 (2)	C7'—C6'—C5'	118.9 (2)
C8—C7—C6	121.8 (2)	C8'—C7'—C6'	122.3 (2)
C8—C7—H7	119.1	C8'—C7'—H7'	118.9
C6—C7—H7	119.1	C6'—C7'—H7'	118.9
C7—C8—C9	119.7 (2)	C7'—C8'—C9'	118.3 (2)
C7—C8—C11	121.4 (2)	C7'—C8'—C11'	122.5 (2)
C9—C8—C11	118.5 (2)	C9'—C8'—C11'	118.4 (2)
C10—C9—C8	119.4 (2)	C10'—C9'—C8'	120.6 (2)
C10—C9—C16	121.1 (2)	C10'—C9'—C16'	118.8 (2)
C8—C9—C16	119.1 (2)	C8'—C9'—C16'	120.2 (2)
C9—C10—C5	121.6 (2)	C9'—C10'—C5'	121.8 (2)
C9—C10—H10	119.2	C9'—C10'—H10'	119.1
C5—C10—H10	119.2	C5'—C10'—H10'	119.1
O1—C11—C12	122.4 (3)	O1'—C11'—C12'	119.2 (2)
O1—C11—C8	118.9 (2)	O1'—C11'—C8'	119.0 (2)
C12—C11—C8	118.7 (2)	C12'—C11'—C8'	121.8 (2)
C13—C12—C11	129.1 (2)	C13'—C12'—C11'	131.4 (3)
C13—C12—S1	111.06 (19)	C13'—C12'—S1'	111.6 (2)
C11—C12—S1	119.6 (2)	C11'—C12'—S1'	116.94 (19)
C12—C13—C14	112.7 (2)	C12'—C13'—C14'	110.2 (3)
C12—C13—H13	123.6	C12'—C13'—H13'	124.9
C14—C13—H13	123.6	C14'—C13'—H13'	124.9
C15—C14—C13	112.1 (3)	C15'—C14'—C13'	113.9 (3)
C15—C14—H14	123.9	C15'—C14'—H14'	123.1
C13—C14—H14	123.9	C13'—C14'—H14'	123.1
C14—C15—S1	113.0 (2)	C14'—C15'—S1'	112.5 (3)
C14—C15—H15	123.5	C14'—C15'—H15'	123.8
S1—C15—H15	123.5	S1'—C15'—H15'	123.8
O2—C16—C17	121.2 (2)	O2'—C16'—C17'	122.2 (2)
O2—C16—C9	120.0 (2)	O2'—C16'—C9'	120.0 (2)
C17—C16—C9	118.7 (2)	C17'—C16'—C9'	117.8 (2)
C18—C17—C16	129.5 (2)	C18'—C17'—C16'	128.5 (2)
C18—C17—S2	111.64 (19)	C18'—C17'—S2'	110.8 (2)
C16—C17—S2	118.83 (19)	C16'—C17'—S2'	120.4 (2)
C17—C18—C19	110.7 (3)	C17'—C18'—C19'	111.8 (3)
C17—C18—H18	124.6	C17'—C18'—H18'	124.1
C19—C18—H18	124.6	C19'—C18'—H18'	124.1
C20—C19—C18	113.7 (3)	C20'—C19'—C18'	112.8 (4)
C20—C19—H19	123.2	C20'—C19'—H19'	123.6
C18—C19—H19	123.2	C18'—C19'—H19'	123.6
C19—C20—S2	112.8 (2)	C19'—C20'—S2'	113.2 (3)
C19—C20—H20	123.6	C19'—C20'—H20'	123.4
S2—C20—H20	123.6	S2'—C20'—H20'	123.4
C6—C1—C2—C3	0.1 (4)	C6'—C1'—C2'—C3'	2.6 (6)
C1—C2—C3—C4	0.2 (4)	C1'—C2'—C3'—C4'	−1.5 (6)
C2—C3—C4—C5	0.3 (4)	C2'—C3'—C4'—C5'	0.1 (5)
C3—C4—C5—C10	−178.8 (2)	C3'—C4'—C5'—C10'	−178.0 (3)
C3—C4—C5—C6	−1.2 (3)	C3'—C4'—C5'—C6'	0.3 (4)
C2—C1—C6—C7	177.9 (3)	C2'—C1'—C6'—C7'	174.7 (3)
C2—C1—C6—C5	−1.0 (4)	C2'—C1'—C6'—C5'	−2.1 (5)
C10—C5—C6—C1	179.2 (2)	C4'—C5'—C6'—C1'	0.7 (4)
C4—C5—C6—C1	1.5 (3)	C10'—C5'—C6'—C1'	179.1 (3)
C10—C5—C6—C7	0.3 (3)	C4'—C5'—C6'—C7'	−176.3 (2)
C4—C5—C6—C7	−177.5 (2)	C10'—C5'—C6'—C7'	2.1 (4)
C1—C6—C7—C8	−177.3 (2)	C1'—C6'—C7'—C8'	−177.8 (3)
C5—C6—C7—C8	1.6 (3)	C5'—C6'—C7'—C8'	−1.0 (4)
C6—C7—C8—C9	−2.8 (3)	C6'—C7'—C8'—C9'	−1.3 (4)
C6—C7—C8—C11	169.7 (2)	C6'—C7'—C8'—C11'	168.4 (2)
C7—C8—C9—C10	2.0 (3)	C7'—C8'—C9'—C10'	2.4 (4)
C11—C8—C9—C10	−170.7 (2)	C11'—C8'—C9'—C10'	−167.7 (2)
C7—C8—C9—C16	−171.7 (2)	C7'—C8'—C9'—C16'	−170.7 (2)
C11—C8—C9—C16	15.6 (3)	C11'—C8'—C9'—C16'	19.2 (3)
C8—C9—C10—C5	−0.1 (3)	C8'—C9'—C10'—C5'	−1.2 (4)
C16—C9—C10—C5	173.5 (2)	C16'—C9'—C10'—C5'	171.9 (2)
C4—C5—C10—C9	176.6 (2)	C4'—C5'—C10'—C9'	177.3 (3)
C6—C5—C10—C9	−1.0 (3)	C6'—C5'—C10'—C9'	−1.0 (4)
C7—C8—C11—O1	−116.2 (3)	C7'—C8'—C11'—O1'	−139.6 (3)
C9—C8—C11—O1	56.4 (4)	C9'—C8'—C11'—O1'	30.0 (4)
C7—C8—C11—C12	63.0 (3)	C7'—C8'—C11'—C12'	39.7 (4)
C9—C8—C11—C12	−124.5 (3)	C9'—C8'—C11'—C12'	−150.6 (2)
O1—C11—C12—C13	−173.9 (3)	O1'—C11'—C12'—C13'	−172.2 (3)
C8—C11—C12—C13	7.0 (4)	C8'—C11'—C12'—C13'	8.4 (4)
O1—C11—C12—S1	1.0 (4)	O1'—C11'—C12'—S1'	5.0 (4)
C8—C11—C12—S1	−178.11 (18)	C8'—C11'—C12'—S1'	−174.30 (19)
C15—S1—C12—C13	0.2 (2)	C15'—S1'—C12'—C13'	−0.6 (2)
C15—S1—C12—C11	−175.6 (2)	C15'—S1'—C12'—C11'	−178.4 (2)
C11—C12—C13—C14	175.2 (3)	C11'—C12'—C13'—C14'	178.2 (3)
S1—C12—C13—C14	−0.1 (3)	S1'—C12'—C13'—C14'	0.9 (3)
C12—C13—C14—C15	−0.2 (4)	C12'—C13'—C14'—C15'	−0.8 (4)
C13—C14—C15—S1	0.3 (4)	C13'—C14'—C15'—S1'	0.3 (4)
C12—S1—C15—C14	−0.3 (3)	C12'—S1'—C15'—C14'	0.1 (3)
C10—C9—C16—O2	−131.8 (3)	C10'—C9'—C16'—O2'	−117.6 (3)
C8—C9—C16—O2	41.8 (4)	C8'—C9'—C16'—O2'	55.6 (3)
C10—C9—C16—C17	45.5 (3)	C10'—C9'—C16'—C17'	61.4 (3)
C8—C9—C16—C17	−140.8 (2)	C8'—C9'—C16'—C17'	−125.4 (2)
O2—C16—C17—C18	−167.8 (3)	O2'—C16'—C17'—C18'	−164.4 (3)
C9—C16—C17—C18	14.9 (4)	C9'—C16'—C17'—C18'	16.6 (4)
O2—C16—C17—S2	11.8 (4)	O2'—C16'—C17'—S2'	8.2 (4)
C9—C16—C17—S2	−165.52 (19)	C9'—C16'—C17'—S2'	−170.75 (18)
C20—S2—C17—C18	−0.6 (2)	C20'—S2'—C17'—C18'	1.2 (2)
C20—S2—C17—C16	179.7 (2)	C20'—S2'—C17'—C16'	−172.6 (2)
C16—C17—C18—C19	−180.0 (3)	C16'—C17'—C18'—C19'	171.4 (3)
S2—C17—C18—C19	0.4 (3)	S2'—C17'—C18'—C19'	−1.8 (3)
C17—C18—C19—C20	0.1 (4)	C17'—C18'—C19'—C20'	1.6 (4)
C18—C19—C20—S2	−0.6 (4)	C18'—C19'—C20'—S2'	−0.7 (5)
C17—S2—C20—C19	0.7 (3)	C17'—S2'—C20'—C19'	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.53	3.407 (3)	158
C13—H13···Cg1ii	0.93	2.86	3.737 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.53	3.407 (3)	158
C13—H13⋯Cg1ii	0.93	2.86	3.737 (2)	157

Symmetry codes: (i) ; (ii) . Cg1 is the S2/C17–C20 ring centroid.