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

Thenmozhi, S.; SubbiahPandi, A.; Ranjith, S.; Clement, J.A.; MohanaKrishnan, A.K.

doi:10.1107/S1600536808038701

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2432

doi:10.1107/S1600536808038701

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

S. Thenmozhi,^a A. SubbiahPandi,^a ^* S. Ranjith,^a J. Arul Clement ^b and A. K. MohanaKrishnan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 15 October 2008; accepted 19 November 2008; online 26 November 2008)

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 ). 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_r = 348.42
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 1.01
8580 reflections
433 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 3970 Friedel pairs
Flack parameter: 0.02 (5)

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) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ . Cg1 is the S2/C17–C20 ring centroid.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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). Cg1 is the S2/C17–C20 ring centroid.

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	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.

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

Crystal data top

C₂₀H₁₂O₂S₂	F(000) = 720
M_r = 348.42	D_x = 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 = 1.3–28.9°
b = 11.1418 (4) Å	µ = 0.33 mm⁻¹
c = 15.4496 (6) Å	T = 293 K
β = 90.266 (1)°	Block, colourless
V = 1680.69 (10) Å³	0.21 × 0.19 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	8580 independent reflections
Radiation source: fine-focus sealed tube	6591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 28.9°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.800, T_max = 0.950	k = −15→14
21289 measured reflections	l = −20→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0499P)² + 0.3545P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
8580 reflections	Δρ_max = 0.44 e Å⁻³
433 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

C₂₀H₁₂O₂S₂	V = 1680.69 (10) Å³
M_r = 348.42	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.7638 (3) Å	µ = 0.33 mm⁻¹
b = 11.1418 (4) Å	T = 293 K
c = 15.4496 (6) Å	0.21 × 0.19 × 0.16 mm
β = 90.266 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	8580 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6591 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.950	R_int = 0.024
21289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.112	Δρ_max = 0.44 e Å⁻³
S = 1.01	Δρ_min = −0.32 e Å⁻³
8580 reflections	Absolute structure: Flack (1983), 3970 Friedel pairs
433 parameters	Absolute structure parameter: 0.02 (5)
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂O₂S₂
M_r	348.42
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.7638 (3), 11.1418 (4), 15.4496 (6)
β (°)	90.266 (1)
V (Å³)	1680.69 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.21 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.800, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	21289, 8580, 6591
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.679

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 1.01
No. of reflections	8580
No. of parameters	433
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.32
Absolute structure	Flack (1983), 3970 Friedel pairs
Absolute structure parameter	0.02 (5)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Acknowledgements

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.

References

Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cohen, V. I., Rist, N. & Duponchel, C. (1977). J. Pharm. Sci. 66, 1322–1334. PubMed Web of Science Google Scholar
Csaszar, J. & Morvay, J. (1983). Acta Pharm. Hung. 53, 121–128. CAS PubMed Google Scholar
Dzhurayev, A. D., Karimkulov, K. M., Makhsumov, A. G. & Amanov, N. (1992). Khim. Form. Zh. 26, 73–75. CAS Google Scholar
EI-Maghraby, A. A., Haroun, B. & Mohammed, N. A. (1984). Egypt. J. Pharm. Sci. 23, 327–336. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gewald, K., Schinke, E. & Botcher, H. (1996). Chem. Ber. 99, 99–100. Google Scholar
Jones, C. D., Jevnikar, M. G., Pike, A. J., Peters, M. K., Black, L. J., Thompson, A. R., Falcone, J. F. & Clemens, J. A. (1984). J. Med. Chem. 27, 1057–1066. CrossRef CAS PubMed Web of Science Google Scholar
Labat, G. & Halfpenny, J. (2005). Acta Cryst. E61, o2813–o2814. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lakshmi, V. V., Sridhar, P. & Polasa, H. (1985). Indian J. Pharm. Sci. 47, 202–204. CAS Google Scholar
Palani, K., Amaladass, P., Mohanakrishnan, A. K. & Ponnuswamy, M. N. (2006). Acta Cryst. E62, o49–o51. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pellis, G. & West, G. B. (1968). Progress in Medicinal Chemistry, Vol. 5, pp. 320–324. London: Butterworth & Co. Ltd. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar