2-(Pyrene-1-yl)-1,3-dithiane

Fun, H.-K.; Jebas, S.R.; Maity, A.C.; Das, N.K.; Goswami, S.

doi:10.1107/S1600536809010320

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o891

doi:10.1107/S1600536809010320

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2-(Pyrene-1-yl)-1,3-dithiane

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Annada C. Maity,^b Nirmal K. Das ^b and Shyamaprasad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 16 March 2009; accepted 20 March 2009; online 28 March 2009)

In the title compound, C₂₀H₁₆S₂, the pyrene ring is planar [maximum deviation 0.0144 (15) Å] and the dithiane ring adopts a chair conformation. The crystal packing is stabilized by C—H⋯π interactions. An intramolecular C—H⋯S hydrogen bond generates an S(5) ring motif.

Related literature

For thionation reactions, see: Goswami & Maity (2008 ); Goswami et al. (2009 ); Fun et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ). For ring puckering analysis, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₁₆S₂
M_r = 320.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.1424 (1) Å
b = 8.6016 (1) Å
c = 24.5049 (2) Å
V = 1505.48 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 100 K
0.36 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.885, T_max = 0.962
29712 measured reflections
6424 independent reflections
5501 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.092
S = 1.05
6424 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 2662 Friedel pairs
Flack parameter: 0.03 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯S2	0.93	2.65	3.0416 (13)	106
C9—H9A⋯Cg1ⁱ	0.93	2.68	3.4196 (15)	137
C4—H4A⋯Cg2ⁱⁱ	0.93	2.98	3.8073 (16)	149
C20—H20A⋯Cg3ⁱⁱⁱ	0.97	2.78	3.5339 (15)	135
Symmetry codes: (i) $[x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{5\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x-1, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring, Cg2 is the centroid of the C1/C6–C10 ring and Cg3 is the centroid of the C2/C3/C13–C16 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010320/at2745sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010320/at2745Isup2.hkl

checkCIF report

Comment top

Thioacetal protection of carbonyl groups is of paramount importance in synthetic organic chemistry and hence the development of novel thionation reactions remains of great interest (Goswami & Maity, 2008; Fun et al., 2009; Goswami et al., 2009). In addition, thioacetals are also utilized as masked acyl anions or masked methylene functions in carbon-carbon bond forming reactions. Here we report the synthesis of 2-pyrene-1-yl-[1,3]dithiane from pyrene-1-aldehyde using BF₃—Et₂O as catalyst and its crystal structure.

The asymmetric unit of (I), (Fig. 1), consists of one molecule of the title compound. The bond lengths (Allen et al., 1987) and bond angles are found to have normal values. The pyrene ring is essentially planar with the maximum deviation from planarity being 0.0144 (15)Å for atom C15. The dithiane group adopts a chair conformation with the puckering parameters Q = 0.7477 (12) Å, θ = 9.61 (10)° and ϕ = 66.3 (5)° (Cremer & Pople, 1975).

The crystal packing is stabilized by C—H···π interactions (Table 1). An intramolecular C—H···S hydrogen bonding generates an S(5) ring motif (Bernstein et al., 1995).

Related literature top

For thionation reactions, see: Goswami & Maity (2008); Goswami et al. (2009); Fun et al. (2009). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). For ring puckering analysis, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1–C6 ring, Cg2 is the centroid of the C1/C6–C10 ring and Cg3 is the centroid of the C2/C3/C13–C16 ring.

Experimental top

To a stirred solution of pyrene-1-aldehyde (500 mg., 2.17 mmol) and boron trifluoride etherate (0.5 ml) in dichloromethane (50 ml) cooled at 273 K is added 1,3-propanedithiol (490 mg, 4.5 mmol) dropwise over 15 min with stirring. The mixture is stirred at room temperature for 3 h. The progress of the reaction is monitored by TLC. After completion of the reaction, NaHCO₃ solution is added slowly and carefully to neutralize the mixture at room temperature which is then extracted with dichloromethane. The organic layer is dried (anhydrous Na₂SO₄) and then the solvent is removed under reduced pressure. The crude product was purified by column chromatography using silica gel with 10% ethyl acetate in pet ether as eluant to afford 2-pyrene-1-yl-[1,3]dithiane (620 mg, 89%) as a colourless crystalline solid along with other thiane derivatives.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate the hydrogen bonding.

2-(Pyrene-1-yl)-1,3-dithiane top

Crystal data top

C₂₀H₁₆S₂	F(000) = 672
M_r = 320.45	D_x = 1.414 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9340 reflections
a = 7.1424 (1) Å	θ = 2.5–33.7°
b = 8.6016 (1) Å	µ = 0.35 mm⁻¹
c = 24.5049 (2) Å	T = 100 K
V = 1505.48 (3) Å³	Block, colourless
Z = 4	0.36 × 0.17 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6424 independent reflections
Radiation source: fine-focus sealed tube	5501 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 35.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.885, T_max = 0.962	k = −13→13
29712 measured reflections	l = −39→39

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0461P)² + 0.0807P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.004
6424 reflections	Δρ_max = 0.48 e Å⁻³
199 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2662 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (5)

Crystal data top

C₂₀H₁₆S₂	V = 1505.48 (3) Å³
M_r = 320.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.1424 (1) Å	µ = 0.35 mm⁻¹
b = 8.6016 (1) Å	T = 100 K
c = 24.5049 (2) Å	0.36 × 0.17 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6424 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5501 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.962	R_int = 0.041
29712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.48 e Å⁻³
S = 1.05	Δρ_min = −0.27 e Å⁻³
6424 reflections	Absolute structure: Flack (1983), 2662 Friedel pairs
199 parameters	Absolute structure parameter: 0.03 (5)
0 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.38288 (5)	0.10233 (4)	0.977454 (13)	0.01668 (8)
S2	0.68513 (5)	−0.07534 (4)	1.037145 (12)	0.01665 (8)
C1	0.6709 (2)	−0.12016 (15)	0.77433 (5)	0.0134 (2)
C2	0.73272 (19)	−0.07300 (16)	0.82744 (5)	0.0131 (2)
C3	0.9112 (2)	−0.00108 (16)	0.83308 (5)	0.0140 (2)
C4	1.0265 (2)	0.01927 (17)	0.78565 (6)	0.0173 (3)
H4A	1.1443	0.0640	0.7894	0.021*
C5	0.9675 (2)	−0.02513 (17)	0.73559 (6)	0.0177 (3)
H5A	1.0456	−0.0107	0.7057	0.021*
C6	0.7869 (2)	−0.09392 (16)	0.72787 (5)	0.0156 (3)
C7	0.7187 (2)	−0.13545 (17)	0.67611 (5)	0.0180 (3)
H7A	0.7932	−0.1193	0.6455	0.022*
C8	0.5425 (2)	−0.19998 (17)	0.66994 (6)	0.0190 (3)
H8A	0.4998	−0.2264	0.6353	0.023*
C9	0.4287 (2)	−0.22556 (16)	0.71502 (5)	0.0180 (3)
H9A	0.3102	−0.2682	0.7103	0.022*
C10	0.4912 (2)	−0.18750 (16)	0.76761 (5)	0.0145 (2)
C11	0.3773 (2)	−0.21097 (16)	0.81490 (5)	0.0162 (3)
H11A	0.2612	−0.2588	0.8110	0.019*
C12	0.4341 (2)	−0.16537 (17)	0.86520 (5)	0.0155 (3)
H12A	0.3555	−0.1810	0.8950	0.019*
C13	0.61341 (19)	−0.09331 (15)	0.87345 (5)	0.0129 (2)
C14	0.6739 (2)	−0.03780 (15)	0.92506 (5)	0.0139 (2)
C15	0.8468 (2)	0.03716 (16)	0.92932 (5)	0.0159 (3)
H15A	0.8838	0.0771	0.9629	0.019*
C16	0.9649 (2)	0.05354 (16)	0.88468 (5)	0.0164 (3)
H16A	1.0808	0.1012	0.8890	0.020*
C17	0.54924 (19)	−0.05773 (15)	0.97455 (5)	0.0142 (2)
H17A	0.4780	−0.1542	0.9698	0.017*
C18	0.2364 (2)	0.03068 (18)	1.03263 (5)	0.0201 (3)
H18A	0.1366	0.1049	1.0391	0.024*
H18B	0.1791	−0.0663	1.0213	0.024*
C19	0.3411 (2)	0.00340 (18)	1.08623 (5)	0.0184 (3)
H19A	0.3993	0.1001	1.0975	0.022*
H19B	0.2516	−0.0259	1.1142	0.022*
C20	0.4911 (2)	−0.12196 (17)	1.08241 (5)	0.0174 (3)
H20A	0.4331	−0.2175	1.0699	0.021*
H20B	0.5404	−0.1410	1.1187	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01679 (16)	0.01854 (16)	0.01470 (14)	0.00372 (13)	−0.00236 (11)	0.00034 (12)
S2	0.01684 (15)	0.02099 (17)	0.01214 (13)	0.00328 (14)	−0.00233 (11)	0.00104 (12)
C1	0.0165 (6)	0.0116 (5)	0.0120 (5)	0.0012 (5)	−0.0008 (4)	−0.0008 (4)
C2	0.0142 (6)	0.0121 (6)	0.0131 (5)	0.0004 (5)	−0.0012 (4)	0.0010 (4)
C3	0.0131 (6)	0.0128 (6)	0.0160 (5)	0.0010 (5)	−0.0021 (5)	0.0015 (4)
C4	0.0148 (7)	0.0169 (6)	0.0203 (6)	0.0002 (5)	0.0011 (5)	0.0020 (5)
C5	0.0171 (7)	0.0185 (7)	0.0177 (6)	0.0019 (5)	0.0038 (5)	0.0024 (5)
C6	0.0174 (6)	0.0145 (6)	0.0148 (5)	0.0021 (5)	0.0004 (4)	0.0012 (5)
C7	0.0236 (7)	0.0177 (7)	0.0128 (6)	0.0025 (5)	0.0003 (5)	0.0001 (5)
C8	0.0256 (7)	0.0182 (7)	0.0133 (6)	0.0021 (6)	−0.0034 (5)	−0.0019 (5)
C9	0.0216 (7)	0.0158 (6)	0.0166 (6)	−0.0008 (5)	−0.0035 (5)	−0.0020 (5)
C10	0.0178 (6)	0.0124 (6)	0.0134 (5)	0.0001 (5)	−0.0017 (5)	−0.0019 (4)
C11	0.0159 (6)	0.0169 (6)	0.0159 (6)	−0.0033 (5)	−0.0015 (5)	−0.0010 (5)
C12	0.0159 (6)	0.0164 (6)	0.0141 (5)	−0.0028 (5)	0.0002 (5)	0.0007 (5)
C13	0.0153 (6)	0.0103 (5)	0.0130 (5)	0.0004 (5)	−0.0015 (4)	0.0001 (4)
C14	0.0151 (6)	0.0133 (6)	0.0133 (5)	0.0012 (5)	−0.0021 (5)	0.0003 (4)
C15	0.0181 (7)	0.0157 (6)	0.0138 (5)	−0.0010 (5)	−0.0043 (5)	−0.0001 (5)
C16	0.0147 (6)	0.0160 (6)	0.0186 (6)	−0.0016 (5)	−0.0027 (5)	0.0016 (5)
C17	0.0163 (6)	0.0148 (6)	0.0115 (5)	0.0014 (5)	−0.0024 (4)	−0.0008 (4)
C18	0.0154 (6)	0.0269 (7)	0.0179 (6)	0.0021 (6)	−0.0001 (5)	−0.0018 (5)
C19	0.0212 (7)	0.0212 (7)	0.0128 (5)	0.0008 (6)	0.0005 (5)	−0.0010 (5)
C20	0.0207 (7)	0.0179 (7)	0.0136 (5)	−0.0005 (6)	0.0001 (5)	0.0018 (5)

Geometric parameters (Å, º) top

S1—C18	1.8173 (15)	C9—H9A	0.9300
S1—C17	1.8200 (14)	C10—C11	1.4301 (19)
S2—C20	1.8200 (15)	C11—C12	1.3557 (18)
S2—C17	1.8214 (13)	C11—H11A	0.9300
C1—C10	1.418 (2)	C12—C13	1.4373 (19)
C1—C6	1.4260 (18)	C12—H12A	0.9300
C1—C2	1.4328 (17)	C13—C14	1.4191 (17)
C2—C3	1.4239 (19)	C14—C15	1.397 (2)
C2—C13	1.4242 (17)	C14—C17	1.5144 (18)
C3—C16	1.4024 (18)	C15—C16	1.3884 (19)
C3—C4	1.4349 (19)	C15—H15A	0.9300
C4—C5	1.3521 (19)	C16—H16A	0.9300
C4—H4A	0.9300	C17—H17A	0.9800
C5—C6	1.432 (2)	C18—C19	1.5298 (19)
C5—H5A	0.9300	C18—H18A	0.9700
C6—C7	1.4047 (18)	C18—H18B	0.9700
C7—C8	1.384 (2)	C19—C20	1.523 (2)
C7—H7A	0.9300	C19—H19A	0.9700
C8—C9	1.389 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—H20A	0.9700
C9—C10	1.4025 (18)	C20—H20B	0.9700

C18—S1—C17	98.54 (7)	C13—C12—H12A	119.4
C20—S2—C17	97.23 (6)	C14—C13—C2	118.82 (12)
C10—C1—C6	119.86 (11)	C14—C13—C12	122.81 (12)
C10—C1—C2	120.01 (12)	C2—C13—C12	118.34 (11)
C6—C1—C2	120.09 (12)	C15—C14—C13	119.42 (12)
C3—C2—C13	120.81 (11)	C15—C14—C17	120.80 (11)
C3—C2—C1	119.16 (12)	C13—C14—C17	119.77 (12)
C13—C2—C1	120.00 (12)	C16—C15—C14	121.66 (12)
C16—C3—C2	118.55 (12)	C16—C15—H15A	119.2
C16—C3—C4	122.18 (13)	C14—C15—H15A	119.2
C2—C3—C4	119.21 (12)	C15—C16—C3	120.69 (13)
C5—C4—C3	121.43 (14)	C15—C16—H16A	119.7
C5—C4—H4A	119.3	C3—C16—H16A	119.7
C3—C4—H4A	119.3	C14—C17—S1	109.24 (9)
C4—C5—C6	121.17 (13)	C14—C17—S2	111.75 (9)
C4—C5—H5A	119.4	S1—C17—S2	112.20 (7)
C6—C5—H5A	119.4	C14—C17—H17A	107.8
C7—C6—C1	118.64 (13)	S1—C17—H17A	107.8
C7—C6—C5	122.46 (12)	S2—C17—H17A	107.8
C1—C6—C5	118.89 (11)	C19—C18—S1	114.16 (10)
C8—C7—C6	121.05 (13)	C19—C18—H18A	108.7
C8—C7—H7A	119.5	S1—C18—H18A	108.7
C6—C7—H7A	119.5	C19—C18—H18B	108.7
C7—C8—C9	120.58 (13)	S1—C18—H18B	108.7
C7—C8—H8A	119.7	H18A—C18—H18B	107.6
C9—C8—H8A	119.7	C20—C19—C18	113.57 (11)
C8—C9—C10	120.51 (14)	C20—C19—H19A	108.9
C8—C9—H9A	119.7	C18—C19—H19A	108.9
C10—C9—H9A	119.7	C20—C19—H19B	108.9
C9—C10—C1	119.35 (13)	C18—C19—H19B	108.9
C9—C10—C11	122.04 (13)	H19A—C19—H19B	107.7
C1—C10—C11	118.60 (11)	C19—C20—S2	114.65 (10)
C12—C11—C10	121.71 (13)	C19—C20—H20A	108.6
C12—C11—H11A	119.1	S2—C20—H20A	108.6
C10—C11—H11A	119.1	C19—C20—H20B	108.6
C11—C12—C13	121.29 (13)	S2—C20—H20B	108.6
C11—C12—H12A	119.4	H20A—C20—H20B	107.6

C10—C1—C2—C3	−178.01 (12)	C10—C11—C12—C13	−1.0 (2)
C6—C1—C2—C3	−0.47 (19)	C3—C2—C13—C14	1.21 (19)
C10—C1—C2—C13	−0.20 (19)	C1—C2—C13—C14	−176.56 (12)
C6—C1—C2—C13	177.34 (12)	C3—C2—C13—C12	179.43 (12)
C13—C2—C3—C16	−1.84 (19)	C1—C2—C13—C12	1.66 (19)
C1—C2—C3—C16	175.95 (13)	C11—C12—C13—C14	177.07 (13)
C13—C2—C3—C4	−179.16 (13)	C11—C12—C13—C2	−1.1 (2)
C1—C2—C3—C4	−1.37 (19)	C2—C13—C14—C15	0.97 (19)
C16—C3—C4—C5	−175.68 (14)	C12—C13—C14—C15	−177.17 (13)
C2—C3—C4—C5	1.5 (2)	C2—C13—C14—C17	179.86 (12)
C3—C4—C5—C6	0.2 (2)	C12—C13—C14—C17	1.7 (2)
C10—C1—C6—C7	0.25 (19)	C13—C14—C15—C16	−2.6 (2)
C2—C1—C6—C7	−177.30 (13)	C17—C14—C15—C16	178.56 (12)
C10—C1—C6—C5	179.72 (13)	C14—C15—C16—C3	1.9 (2)
C2—C1—C6—C5	2.17 (19)	C2—C3—C16—C15	0.3 (2)
C4—C5—C6—C7	177.38 (14)	C4—C3—C16—C15	177.52 (13)
C4—C5—C6—C1	−2.1 (2)	C15—C14—C17—S1	93.99 (13)
C1—C6—C7—C8	0.3 (2)	C13—C14—C17—S1	−84.88 (13)
C5—C6—C7—C8	−179.18 (13)	C15—C14—C17—S2	−30.77 (16)
C6—C7—C8—C9	−0.2 (2)	C13—C14—C17—S2	150.36 (10)
C7—C8—C9—C10	−0.5 (2)	C18—S1—C17—C14	171.69 (9)
C8—C9—C10—C1	1.0 (2)	C18—S1—C17—S2	−63.82 (9)
C8—C9—C10—C11	179.45 (13)	C20—S2—C17—C14	−172.85 (9)
C6—C1—C10—C9	−0.88 (19)	C20—S2—C17—S1	64.05 (8)
C2—C1—C10—C9	176.67 (13)	C17—S1—C18—C19	59.16 (12)
C6—C1—C10—C11	−179.38 (13)	S1—C18—C19—C20	−63.42 (15)
C2—C1—C10—C11	−1.83 (19)	C18—C19—C20—S2	65.04 (15)
C9—C10—C11—C12	−175.99 (14)	C17—S2—C20—C19	−61.20 (11)
C1—C10—C11—C12	2.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S2	0.93	2.65	3.0416 (13)	106
C9—H9A···Cg1ⁱ	0.93	2.68	3.4196 (15)	137
C4—H4A···Cg2ⁱⁱ	0.93	2.98	3.8073 (16)	149
C20—H20A···Cg3ⁱⁱⁱ	0.97	2.78	3.5339 (15)	135

Symmetry codes: (i) x+3/2, −y−1/2, −z+1; (ii) x+5/2, −y+1/2, −z+1; (iii) −x−1, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆S₂
M_r	320.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.1424 (1), 8.6016 (1), 24.5049 (2)
V (Å³)	1505.48 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.36 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.885, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	29712, 6424, 5501
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.809

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.092, 1.05
No. of reflections	6424
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.27
Absolute structure	Flack (1983), 2662 Friedel pairs
Absolute structure parameter	0.03 (5)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S2	0.93	2.65	3.0416 (13)	106
C9—H9A···Cg1ⁱ	0.93	2.68	3.4196 (15)	137
C4—H4A···Cg2ⁱⁱ	0.93	2.98	3.8073 (16)	149
C20—H20A···Cg3ⁱⁱⁱ	0.97	2.78	3.5339 (15)	135

Symmetry codes: (i) x+3/2, −y−1/2, −z+1; (ii) x+5/2, −y+1/2, −z+1; (iii) −x−1, y−1/2, −z+5/2.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. ACM, NKD and SG thank the DST [SR/S1/OC-13/2005], Government of India, for financial support. ACM and NKD thank the UGC, Government of India, for awarding them each a fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354—1358. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Kia, R., Maity, A. C. & Goswami, S. (2009). Acta Cryst. E65, o173. Web of Science CSD CrossRef IUCr Journals Google Scholar
Goswami, S. P. & Maity, A. C. (2008). Tetrahedron Lett. 49, 3092–3096. Web of Science CrossRef CAS Google Scholar
Goswami, S. P., Maity, A. C., Fun, H. K. & Chantrapromma, S. (2009). Eur. J. Org. Chem. pp. 1417–1426. CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar