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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2432.
Published online 2008 November 26. doi:  10.1107/S1600536808038701
PMCID: PMC2959828

Naphthalene-2,3-diylbis[(2-thien­yl)methanone]

Abstract

The asymmetric unit of the title compound, C20H12O2S2, contains two crystallographically independent mol­ecules 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 inter­actions.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o2432-scheme1.jpg

Experimental

Crystal data

  • C20H12O2S2
  • M r = 348.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2432-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 3970 Friedel pairs
  • Flack parameter: 0.02 (5)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

ST and ASP thank Dr J. Jothi Kumar, Principal of Presidency College (Autonomous), Chennai, for providing computer and internet facilities. Dr Babu Vargheese, SAIF, IIT, Madras, India, is thanked for his help with the data collection.

supplementary crystallographic information

Comment

Sulfur containing Schiff bases (Pellis & West, 1968; Cohen et al., 1977; Csaszar & Morvay,1983; Lakshmi et al., 1985), and their thiophene derivatives (EI-Maghraby et al., 1984; Dzhurayev et al., 1992), possess pharmacological activities such as anti-bacterial, anti-cancer, anti-inflammatory and anti-toxic properties (Gewald et al., 1996). Benzo(b)thiophene analogs have been shown to possess interesting estrogenic and antiestrogenic effects. Some of these compounds inhibit estradiol with greater potency than tamoxifen, and inhibition of the growth of DMBA induced mammary tumors by such compounds has been reported (Jones et al., 1984). Some of the thiophene derivatives were screened against gram-positive, gram-negative bacteria and have shown promising anti-bacterial activity (Palani et al., 2006). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). The corresponding bond lengths and angles of the two molecules agree with each other, and are comparable to those observed in the structure of 1,5-bis(3-thienyloxy)-3-oxapentane (Labat & Halfpenny, 2005). The two independent molecules differ in the orientations of thienylmethanone units with respect to the naphthalene ring system. The S1/C12-C15 and S2/C17-C20 rings form dihedral angles of 65.30 (11)° and 50.94 (11)°, respectively, with the C1-C10 naphthalene ring system, whereas, the S1'/C12'-C15' and S2'/C17'-C20' rings form dihedral angles of 41.94 (12)° and 69.61 (13)°, respectively, with the C1'-C10' naphthalene ring system.

The crystal structure is stabilized by C–H···O and C–H···π interactions (Table 1 and Fig.2).

Experimental

A mixture of phthalaldehyde (1 g, 7.46 mmol) and 1,4-di(thiophene-2-yl)butane- 1,4-diane (1.86 g 7.46 mmol) was dissolved in ethanol and tertiary-butane oxide (2.08 g, 18.6 mmol), and then allowed to stir for 4 h at room temperature to get the product. The crude product was filtered and then recrystallized in chloroform. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a chloroform solution at room temperature.

Refinement

All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C-H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C20H12O2S2F000 = 720
Mr = 348.42Dx = 1.377 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8580 reflections
a = 9.7638 (3) Åθ = 1.3–28.9º
b = 11.1418 (4) ŵ = 0.33 mm1
c = 15.4496 (6) ÅT = 293 (2) K
β = 90.266 (1)ºBlock, colourless
V = 1680.69 (10) Å30.21 × 0.19 × 0.16 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer8580 independent reflections
Radiation source: fine-focus sealed tube6591 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 293(2) Kθmax = 28.9º
ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.800, Tmax = 0.950k = −15→14
21289 measured reflectionsl = −20→17

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.01Δρmax = 0.44 e Å3
8580 reflectionsΔρmin = −0.32 e Å3
433 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 3970 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (5)
Secondary atom site location: difference Fourier map

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 (Å2)

xyzUiso*/Ueq
S10.06339 (8)−0.02637 (6)0.45118 (6)0.0657 (2)
S20.33739 (8)0.44467 (8)0.69777 (5)0.0644 (2)
O10.0949 (2)0.24092 (19)0.44816 (17)0.0822 (7)
O20.3446 (3)0.24071 (18)0.57466 (14)0.0815 (7)
C10.4852 (3)0.3351 (2)0.18008 (17)0.0542 (6)
H10.44680.27850.14290.065*
C20.5757 (3)0.4164 (3)0.14849 (18)0.0609 (7)
H20.59840.41480.09010.073*
C30.6350 (3)0.5021 (3)0.20256 (18)0.0571 (6)
H30.69660.55740.18000.069*
C40.6032 (2)0.5053 (2)0.28836 (17)0.0488 (6)
H40.64300.56310.32390.059*
C50.5102 (2)0.42129 (19)0.32380 (15)0.0398 (5)
C60.4485 (2)0.3350 (2)0.26773 (16)0.0421 (5)
C70.3516 (2)0.2545 (2)0.30259 (16)0.0451 (5)
H70.31270.19660.26680.054*
C80.3135 (2)0.25942 (19)0.38716 (16)0.0434 (5)
C90.3768 (2)0.3442 (2)0.44373 (16)0.0442 (5)
C100.4727 (2)0.4227 (2)0.41136 (15)0.0428 (5)
H100.51370.47790.44840.051*
C110.1943 (3)0.1879 (2)0.42024 (19)0.0508 (6)
C120.2010 (2)0.0578 (2)0.41656 (16)0.0448 (5)
C130.3071 (2)−0.0134 (2)0.39437 (17)0.0484 (6)
H130.39030.01560.37410.058*
C140.2781 (3)−0.1368 (2)0.4053 (2)0.0608 (7)
H140.3397−0.19800.39290.073*
C150.1515 (3)−0.1553 (3)0.4355 (2)0.0653 (8)
H150.1158−0.23100.44670.078*
C160.3484 (3)0.3376 (2)0.53847 (17)0.0506 (6)
C170.3315 (2)0.4492 (2)0.58672 (15)0.0456 (5)
C180.3095 (3)0.5646 (2)0.55646 (19)0.0521 (6)
H180.30260.58540.49830.062*
C190.2991 (3)0.6466 (3)0.6262 (2)0.0696 (8)
H190.28410.72840.61860.084*
C200.3127 (3)0.5957 (3)0.7037 (2)0.0722 (9)
H200.30910.63810.75550.087*
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)
H1'0.70530.05750.71970.083*
C2'0.8959 (4)0.0362 (2)0.6773 (2)0.0730 (9)
H2'0.8777−0.03190.64450.088*
C3'1.0280 (3)0.0812 (2)0.6812 (2)0.0677 (8)
H3'1.09810.04210.65210.081*
C4'1.0559 (3)0.1833 (2)0.7278 (2)0.0597 (7)
H4'1.14490.21300.73000.072*
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)
H7'0.62070.23200.80610.063*
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)
H10'1.06200.38140.82240.059*
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)
H13'0.50980.21480.93400.067*
C14'0.3192 (3)0.2820 (3)0.9735 (2)0.0713 (9)
H14'0.27520.21260.99210.086*
C15'0.2605 (3)0.3915 (3)0.9763 (2)0.0723 (9)
H15'0.17270.40560.99700.087*
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)
H18'0.95810.59640.74720.069*
C19'1.0413 (4)0.7619 (3)0.7816 (3)0.0902 (12)
H19'1.05480.79750.72780.108*
C20'1.0736 (4)0.8144 (3)0.8562 (3)0.0952 (14)
H20'1.11300.89020.86000.114*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0555 (4)0.0583 (4)0.0835 (5)−0.0129 (3)0.0201 (4)−0.0068 (4)
S20.0706 (5)0.0755 (5)0.0471 (4)−0.0149 (4)0.0070 (3)−0.0040 (4)
O10.0665 (13)0.0542 (12)0.126 (2)0.0072 (10)0.0366 (13)−0.0069 (13)
O20.135 (2)0.0491 (11)0.0603 (13)0.0066 (12)0.0098 (13)0.0124 (10)
C10.0642 (17)0.0556 (15)0.0428 (15)−0.0048 (12)−0.0067 (12)−0.0048 (12)
C20.0709 (19)0.0683 (18)0.0437 (15)−0.0089 (15)0.0013 (14)0.0006 (13)
C30.0580 (15)0.0573 (15)0.0562 (16)−0.0080 (13)0.0039 (13)0.0054 (13)
C40.0466 (13)0.0469 (12)0.0527 (15)−0.0022 (11)−0.0047 (11)−0.0053 (11)
C50.0392 (11)0.0353 (10)0.0448 (13)0.0058 (9)−0.0047 (10)−0.0025 (9)
C60.0440 (12)0.0368 (10)0.0455 (14)0.0039 (9)−0.0051 (10)−0.0031 (9)
C70.0466 (13)0.0396 (11)0.0491 (15)−0.0017 (9)−0.0061 (11)−0.0072 (10)
C80.0438 (12)0.0333 (10)0.0530 (15)0.0032 (9)−0.0011 (11)−0.0019 (10)
C90.0478 (13)0.0389 (11)0.0460 (14)0.0070 (10)−0.0008 (11)−0.0008 (10)
C100.0462 (12)0.0382 (11)0.0439 (13)0.0019 (9)−0.0068 (10)−0.0060 (10)
C110.0481 (14)0.0435 (12)0.0610 (17)0.0015 (10)0.0054 (12)−0.0060 (11)
C120.0433 (13)0.0437 (11)0.0474 (14)−0.0074 (10)−0.0008 (11)−0.0020 (10)
C130.0421 (12)0.0449 (12)0.0582 (16)−0.0006 (10)−0.0013 (11)0.0002 (11)
C140.0656 (18)0.0427 (13)0.074 (2)−0.0007 (12)−0.0019 (15)−0.0039 (13)
C150.074 (2)0.0439 (13)0.078 (2)−0.0143 (13)0.0014 (16)−0.0052 (14)
C160.0563 (15)0.0479 (13)0.0477 (15)−0.0002 (11)0.0008 (12)0.0014 (11)
C170.0433 (12)0.0505 (13)0.0429 (13)−0.0061 (10)0.0021 (10)−0.0061 (11)
C180.0522 (15)0.0505 (13)0.0536 (16)−0.0017 (11)0.0036 (12)−0.0111 (12)
C190.082 (2)0.0509 (15)0.076 (2)−0.0088 (14)0.0077 (17)−0.0145 (15)
C200.085 (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)

Geometric parameters (Å, °)

S1—C151.692 (3)S1'—C15'1.697 (3)
S1—C121.726 (2)S1'—C12'1.720 (3)
S2—C201.702 (4)S2'—C20'1.690 (4)
S2—C171.717 (2)S2'—C17'1.718 (2)
O1—C111.216 (3)O1'—C11'1.222 (3)
O2—C161.216 (3)O2'—C16'1.218 (3)
C1—C21.358 (4)C1'—C2'1.361 (5)
C1—C61.402 (4)C1'—C6'1.412 (4)
C1—H10.93C1'—H1'0.93
C2—C31.393 (4)C2'—C3'1.384 (4)
C2—H20.93C2'—H2'0.93
C3—C41.363 (4)C3'—C4'1.373 (4)
C3—H30.93C3'—H3'0.93
C4—C51.416 (3)C4'—C5'1.404 (4)
C4—H40.93C4'—H4'0.93
C5—C101.403 (3)C5'—C10'1.413 (3)
C5—C61.426 (3)C5'—C6'1.416 (3)
C6—C71.412 (3)C6'—C7'1.412 (4)
C7—C81.361 (4)C7'—C8'1.366 (3)
C7—H70.93C7'—H7'0.93
C8—C91.425 (3)C8'—C9'1.424 (3)
C8—C111.503 (4)C8'—C11'1.482 (4)
C9—C101.377 (3)C9'—C10'1.359 (4)
C9—C161.493 (4)C9'—C16'1.506 (3)
C10—H100.93C10'—H10'0.93
C11—C121.452 (3)C11'—C12'1.461 (4)
C12—C131.350 (3)C12'—C13'1.398 (4)
C13—C141.414 (4)C13'—C14'1.424 (4)
C13—H130.93C13'—H13'0.93
C14—C151.339 (4)C14'—C15'1.348 (5)
C14—H140.93C14'—H14'0.93
C15—H150.93C15'—H15'0.93
C16—C171.459 (4)C16'—C17'1.448 (4)
C17—C181.385 (4)C17'—C18'1.377 (4)
C18—C191.418 (4)C18'—C19'1.414 (4)
C18—H180.93C18'—H18'0.93
C19—C201.330 (5)C19'—C20'1.329 (6)
C19—H190.93C19'—H19'0.93
C20—H200.93C20'—H20'0.93
C15—S1—C1291.10 (14)C15'—S1'—C12'91.82 (16)
C20—S2—C1791.19 (15)C20'—S2'—C17'91.46 (17)
C2—C1—C6121.1 (2)C2'—C1'—C6'121.0 (3)
C2—C1—H1119.4C2'—C1'—H1'119.5
C6—C1—H1119.4C6'—C1'—H1'119.5
C1—C2—C3120.7 (3)C1'—C2'—C3'120.6 (3)
C1—C2—H2119.6C1'—C2'—H2'119.7
C3—C2—H2119.6C3'—C2'—H2'119.7
C4—C3—C2120.4 (3)C4'—C3'—C2'120.4 (3)
C4—C3—H3119.8C4'—C3'—H3'119.8
C2—C3—H3119.8C2'—C3'—H3'119.8
C3—C4—C5120.5 (2)C3'—C4'—C5'120.4 (3)
C3—C4—H4119.7C3'—C4'—H4'119.8
C5—C4—H4119.7C5'—C4'—H4'119.8
C10—C5—C4122.4 (2)C4'—C5'—C10'122.6 (2)
C10—C5—C6118.8 (2)C4'—C5'—C6'119.3 (2)
C4—C5—C6118.7 (2)C10'—C5'—C6'118.1 (2)
C1—C6—C7122.9 (2)C1'—C6'—C7'122.8 (2)
C1—C6—C5118.5 (2)C1'—C6'—C5'118.2 (3)
C7—C6—C5118.6 (2)C7'—C6'—C5'118.9 (2)
C8—C7—C6121.8 (2)C8'—C7'—C6'122.3 (2)
C8—C7—H7119.1C8'—C7'—H7'118.9
C6—C7—H7119.1C6'—C7'—H7'118.9
C7—C8—C9119.7 (2)C7'—C8'—C9'118.3 (2)
C7—C8—C11121.4 (2)C7'—C8'—C11'122.5 (2)
C9—C8—C11118.5 (2)C9'—C8'—C11'118.4 (2)
C10—C9—C8119.4 (2)C10'—C9'—C8'120.6 (2)
C10—C9—C16121.1 (2)C10'—C9'—C16'118.8 (2)
C8—C9—C16119.1 (2)C8'—C9'—C16'120.2 (2)
C9—C10—C5121.6 (2)C9'—C10'—C5'121.8 (2)
C9—C10—H10119.2C9'—C10'—H10'119.1
C5—C10—H10119.2C5'—C10'—H10'119.1
O1—C11—C12122.4 (3)O1'—C11'—C12'119.2 (2)
O1—C11—C8118.9 (2)O1'—C11'—C8'119.0 (2)
C12—C11—C8118.7 (2)C12'—C11'—C8'121.8 (2)
C13—C12—C11129.1 (2)C13'—C12'—C11'131.4 (3)
C13—C12—S1111.06 (19)C13'—C12'—S1'111.6 (2)
C11—C12—S1119.6 (2)C11'—C12'—S1'116.94 (19)
C12—C13—C14112.7 (2)C12'—C13'—C14'110.2 (3)
C12—C13—H13123.6C12'—C13'—H13'124.9
C14—C13—H13123.6C14'—C13'—H13'124.9
C15—C14—C13112.1 (3)C15'—C14'—C13'113.9 (3)
C15—C14—H14123.9C15'—C14'—H14'123.1
C13—C14—H14123.9C13'—C14'—H14'123.1
C14—C15—S1113.0 (2)C14'—C15'—S1'112.5 (3)
C14—C15—H15123.5C14'—C15'—H15'123.8
S1—C15—H15123.5S1'—C15'—H15'123.8
O2—C16—C17121.2 (2)O2'—C16'—C17'122.2 (2)
O2—C16—C9120.0 (2)O2'—C16'—C9'120.0 (2)
C17—C16—C9118.7 (2)C17'—C16'—C9'117.8 (2)
C18—C17—C16129.5 (2)C18'—C17'—C16'128.5 (2)
C18—C17—S2111.64 (19)C18'—C17'—S2'110.8 (2)
C16—C17—S2118.83 (19)C16'—C17'—S2'120.4 (2)
C17—C18—C19110.7 (3)C17'—C18'—C19'111.8 (3)
C17—C18—H18124.6C17'—C18'—H18'124.1
C19—C18—H18124.6C19'—C18'—H18'124.1
C20—C19—C18113.7 (3)C20'—C19'—C18'112.8 (4)
C20—C19—H19123.2C20'—C19'—H19'123.6
C18—C19—H19123.2C18'—C19'—H19'123.6
C19—C20—S2112.8 (2)C19'—C20'—S2'113.2 (3)
C19—C20—H20123.6C19'—C20'—H20'123.4
S2—C20—H20123.6S2'—C20'—H20'123.4
C6—C1—C2—C30.1 (4)C6'—C1'—C2'—C3'2.6 (6)
C1—C2—C3—C40.2 (4)C1'—C2'—C3'—C4'−1.5 (6)
C2—C3—C4—C50.3 (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—C7177.9 (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—C1179.2 (2)C4'—C5'—C6'—C1'0.7 (4)
C4—C5—C6—C11.5 (3)C10'—C5'—C6'—C1'179.1 (3)
C10—C5—C6—C70.3 (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—C81.6 (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—C11169.7 (2)C6'—C7'—C8'—C11'168.4 (2)
C7—C8—C9—C102.0 (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—C1615.6 (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—C5173.5 (2)C16'—C9'—C10'—C5'171.9 (2)
C4—C5—C10—C9176.6 (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—O156.4 (4)C9'—C8'—C11'—O1'30.0 (4)
C7—C8—C11—C1263.0 (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—C137.0 (4)C8'—C11'—C12'—C13'8.4 (4)
O1—C11—C12—S11.0 (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—C130.2 (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—C14175.2 (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—S10.3 (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—O241.8 (4)C8'—C9'—C16'—O2'55.6 (3)
C10—C9—C16—C1745.5 (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—C1814.9 (4)C9'—C16'—C17'—C18'16.6 (4)
O2—C16—C17—S211.8 (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—C16179.7 (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—C190.4 (3)S2'—C17'—C18'—C19'−1.8 (3)
C17—C18—C19—C200.1 (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—C190.7 (3)C17'—S2'—C20'—C19'−0.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.533.407 (3)158
C13—H13···Cg1ii0.932.863.737 (2)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2690).

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