1-Meth­oxy-4-({[(4-meth­oxy­phen­yl)­sulfan­yl](phen­yl)meth­yl}sulfan­yl)benzene

Li, H.; Ramachandran, G.; Sathishkumar, M.; Sathiyanarayanan, K.; Rathore, R.S.

doi:10.1107/S1600536812006320

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o782

doi:10.1107/S1600536812006320

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1-Methoxy-4-({[(4-methoxyphenyl)sulfanyl](phenyl)methyl}sulfanyl)benzene

Hongqi Li,^a ^* G. Ramachandran,^b M. Sathishkumar,^b K. Sathiyanarayanan ^b and R. S. Rathore ^c

^aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, and ^cBioinformatics Infrastructure Facility, Department of Biotechnology, School of Life Sciences, University of Hyderabad, Hyderabad 500 046, India
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 12 February 2012; accepted 13 February 2012; online 17 February 2012)

The title compound, C₂₁H₂₀O₂S₂, forms a propeller-shaped structure with the tetrahedral C atom as the central hub and methoxybenzene and phenyl residues as radiating blades. Short C—H⋯π contacts are observed.

Related literature

For related structures, see: Farrugia et al. (2000 ). For details on the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₂₁H₂₀O₂S₂
M_r = 368.49
Monoclinic, P 2₁ /c
a = 21.1506 (15) Å
b = 5.6114 (3) Å
c = 17.1219 (11) Å
β = 110.336 (2)°
V = 1905.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.42 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.888, T_max = 0.950
12756 measured reflections
4154 independent reflections
2725 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.128
S = 1.02
4154 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg2ⁱ	0.93	2.99	3.713 (3)	136
C10—H10⋯Cg2ⁱⁱ	0.93	2.96	3.610 (2)	128
C21—H21B⋯Cg1ⁱⁱⁱ	0.96	2.98	3.914 (5)	165
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT-Plus (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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006320/tk5059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006320/tk5059Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006320/tk5059Isup3.cml

checkCIF report

Comment top

A search in Cambridge Structural Database (CCDC; version 5.31; Allen, 2002) revealed four similar crystal structures (Farrugia et al., 2000). The title compound, Fig. 1, forms a propeller-shaped structure with the tetrahedral carbon of the phenylmethyl moiety as the central hub and methoxybenzene and phenyl moieties as radiating blades. Short C—H···π contacts stabilize the structure, Table 1.

Related literature top

For related structures, see: Farrugia et al. (2000). For details on the Cambridge Structural Database, see: Allen (2002).

Experimental top

In a dry 100 ml Erlenmeyer flask were placed benzaldehyde (10 mmol), 4-methoxythiophenol (10 mmol), iodine (15 mol %) and dichloromethane (DCM; 15 ml). The reaction mixture was stirred at room temperature for an hour. The reaction was monitored by TLC and after the completion of reaction the iodine utilized was removed from the product by treating it with aqueous sodium thiosulfate solution. The final product was extracted into DCM (2 x 20 ml). The crude reaction mixture was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluents. Final yields: 93%; M.pt: 322 (1) °K. Suitable single crystals of the title compound were grown from its ethanol/tetrahydrofuran mixture (1:1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (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, 2009).

Figures top

Fig. 1. A view of the title compound with non-H atoms shown with 30% probability ellipsoids.

1-Methoxy-4-({[(4-methoxyphenyl)sulfanyl](phenyl)methyl}sulfanyl)benzene top

Crystal data top

C₂₁H₂₀O₂S₂	F(000) = 776
M_r = 368.49	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 322(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.1506 (15) Å	Cell parameters from 4040 reflections
b = 5.6114 (3) Å	θ = 2.5–25.1°
c = 17.1219 (11) Å	µ = 0.29 mm⁻¹
β = 110.336 (2)°	T = 298 K
V = 1905.4 (2) Å³	Rectangular, colourless
Z = 4	0.42 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4154 independent reflections
Radiation source: fine-focus sealed tube	2725 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −27→26
T_min = 0.888, T_max = 0.950	k = −6→7
12756 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0584P)² + 0.5757P] where P = (F_o² + 2F_c²)/3
4154 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₂₀O₂S₂	V = 1905.4 (2) Å³
M_r = 368.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.1506 (15) Å	µ = 0.29 mm⁻¹
b = 5.6114 (3) Å	T = 298 K
c = 17.1219 (11) Å	0.42 × 0.20 × 0.18 mm
β = 110.336 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4154 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2725 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.950	R_int = 0.024
12756 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
4154 reflections	Δρ_min = −0.27 e Å⁻³
228 parameters

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
C1	0.28208 (12)	0.3397 (4)	0.08333 (15)	0.0582 (6)
H1	0.2956	0.2300	0.1267	0.070*
C2	0.30050 (14)	0.3069 (5)	0.01429 (17)	0.0682 (7)
H2	0.3269	0.1764	0.0118	0.082*
C3	0.28023 (12)	0.4651 (5)	−0.05079 (14)	0.0582 (6)
H3	0.2923	0.4412	−0.0975	0.070*
C4	0.24238 (12)	0.6575 (4)	−0.04643 (14)	0.0579 (6)
H4	0.2286	0.7656	−0.0903	0.069*
C5	0.22434 (11)	0.6929 (4)	0.02289 (14)	0.0553 (6)
H5	0.1988	0.8255	0.0255	0.066*
C6	0.24388 (10)	0.5330 (4)	0.08852 (12)	0.0437 (5)
C7	0.22303 (10)	0.5625 (4)	0.16395 (13)	0.0472 (5)
H7	0.2331	0.4144	0.1963	0.057*
C8	0.11543 (10)	0.5823 (4)	0.22356 (13)	0.0465 (5)
C9	0.07731 (10)	0.7557 (4)	0.24299 (13)	0.0498 (5)
H9	0.0650	0.8914	0.2099	0.060*
C10	0.05727 (10)	0.7304 (4)	0.31070 (13)	0.0497 (5)
H10	0.0306	0.8472	0.3223	0.060*
C11	0.07636 (10)	0.5324 (4)	0.36186 (13)	0.0463 (5)
C12	0.11566 (11)	0.3596 (4)	0.34425 (15)	0.0534 (6)
H12	0.1297	0.2275	0.3788	0.064*
C13	0.13406 (11)	0.3849 (4)	0.27413 (15)	0.0561 (6)
H13	0.1594	0.2660	0.2612	0.067*
C14	0.06989 (14)	0.3243 (5)	0.48056 (16)	0.0749 (8)
H14A	0.0515	0.1833	0.4491	0.112*
H14B	0.0514	0.3439	0.5240	0.112*
H14C	0.1180	0.3095	0.5047	0.112*
C15	0.34680 (11)	0.6870 (4)	0.27962 (13)	0.0504 (5)
C16	0.35770 (14)	0.5044 (6)	0.33572 (17)	0.0822 (9)
H16	0.3216	0.4438	0.3486	0.099*
C17	0.42130 (16)	0.4077 (6)	0.37378 (19)	0.0917 (10)
H17	0.4276	0.2804	0.4105	0.110*
C18	0.47508 (14)	0.5028 (6)	0.35644 (17)	0.0741 (8)
C19	0.46437 (15)	0.6859 (6)	0.3018 (2)	0.0877 (9)
H19	0.5007	0.7511	0.2906	0.105*
C20	0.40113 (13)	0.7771 (5)	0.26288 (17)	0.0718 (7)
H20	0.3949	0.9008	0.2248	0.086*
C21	0.5537 (2)	0.2212 (8)	0.4413 (3)	0.1463 (19)
H21A	0.5398	0.2463	0.4884	0.220*
H21B	0.6011	0.1866	0.4603	0.220*
H21C	0.5291	0.0896	0.4090	0.220*
O1	0.05333 (8)	0.5258 (3)	0.42700 (10)	0.0633 (4)
O2	0.54066 (11)	0.4281 (5)	0.39166 (15)	0.1103 (8)
S1	0.13305 (3)	0.61593 (13)	0.12994 (4)	0.0614 (2)
S2	0.26527 (3)	0.80951 (11)	0.23220 (3)	0.05424 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0697 (15)	0.0523 (15)	0.0573 (14)	0.0096 (11)	0.0281 (12)	0.0104 (11)
C2	0.0824 (18)	0.0560 (16)	0.0804 (18)	0.0158 (13)	0.0463 (15)	0.0015 (14)
C3	0.0652 (15)	0.0657 (16)	0.0505 (13)	−0.0064 (12)	0.0287 (11)	−0.0081 (12)
C4	0.0617 (14)	0.0656 (16)	0.0474 (13)	0.0037 (12)	0.0203 (11)	0.0117 (11)
C5	0.0600 (14)	0.0544 (14)	0.0561 (13)	0.0129 (11)	0.0262 (11)	0.0068 (11)
C6	0.0443 (11)	0.0451 (12)	0.0425 (11)	−0.0031 (9)	0.0160 (9)	−0.0024 (9)
C7	0.0485 (11)	0.0502 (13)	0.0447 (11)	−0.0023 (10)	0.0183 (9)	−0.0008 (10)
C8	0.0387 (10)	0.0504 (13)	0.0508 (12)	−0.0041 (9)	0.0162 (9)	−0.0030 (10)
C9	0.0435 (11)	0.0502 (14)	0.0541 (13)	0.0018 (10)	0.0149 (9)	0.0050 (10)
C10	0.0452 (11)	0.0468 (13)	0.0590 (13)	0.0059 (9)	0.0206 (10)	−0.0026 (11)
C11	0.0388 (11)	0.0511 (13)	0.0502 (12)	−0.0024 (9)	0.0169 (9)	−0.0016 (10)
C12	0.0497 (12)	0.0449 (13)	0.0688 (15)	0.0040 (10)	0.0250 (11)	0.0089 (11)
C13	0.0490 (12)	0.0469 (14)	0.0801 (16)	0.0039 (10)	0.0322 (12)	−0.0059 (12)
C14	0.0818 (19)	0.082 (2)	0.0701 (17)	0.0028 (15)	0.0380 (15)	0.0216 (15)
C15	0.0551 (13)	0.0552 (14)	0.0423 (11)	−0.0060 (10)	0.0186 (9)	−0.0050 (10)
C16	0.0661 (17)	0.102 (2)	0.0743 (17)	−0.0057 (16)	0.0187 (14)	0.0297 (17)
C17	0.086 (2)	0.096 (2)	0.077 (2)	0.0070 (18)	0.0083 (16)	0.0303 (17)
C18	0.0609 (16)	0.088 (2)	0.0660 (16)	0.0093 (15)	0.0134 (13)	−0.0180 (15)
C19	0.0616 (17)	0.101 (3)	0.109 (2)	−0.0023 (16)	0.0406 (17)	0.006 (2)
C20	0.0687 (17)	0.0734 (18)	0.0814 (18)	−0.0002 (14)	0.0362 (14)	0.0113 (15)
C21	0.115 (3)	0.132 (4)	0.138 (4)	0.051 (3)	−0.025 (3)	−0.013 (3)
O1	0.0678 (10)	0.0719 (12)	0.0588 (9)	0.0083 (9)	0.0329 (8)	0.0075 (9)
O2	0.0726 (14)	0.136 (2)	0.1071 (17)	0.0291 (14)	0.0116 (12)	−0.0111 (16)
S1	0.0485 (3)	0.0866 (5)	0.0493 (3)	0.0027 (3)	0.0174 (2)	0.0004 (3)
S2	0.0579 (3)	0.0549 (4)	0.0504 (3)	−0.0013 (3)	0.0195 (3)	−0.0066 (3)

Geometric parameters (Å, º) top

C1—C6	1.374 (3)	C12—C13	1.392 (3)
C1—C2	1.379 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.372 (3)	C14—O1	1.421 (3)
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.361 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.381 (3)	C15—C16	1.368 (3)
C4—H4	0.9300	C15—C20	1.374 (3)
C5—C6	1.384 (3)	C15—S2	1.770 (2)
C5—H5	0.9300	C16—C17	1.385 (4)
C6—C7	1.512 (3)	C16—H16	0.9300
C7—S1	1.811 (2)	C17—C18	1.379 (4)
C7—S2	1.833 (2)	C17—H17	0.9300
C7—H7	0.9800	C18—C19	1.354 (4)
C8—C9	1.376 (3)	C18—O2	1.372 (3)
C8—C13	1.377 (3)	C19—C20	1.370 (4)
C8—S1	1.778 (2)	C19—H19	0.9300
C9—C10	1.373 (3)	C20—H20	0.9300
C9—H9	0.9300	C21—O2	1.408 (5)
C10—C11	1.385 (3)	C21—H21A	0.9600
C10—H10	0.9300	C21—H21B	0.9600
C11—O1	1.364 (2)	C21—H21C	0.9600
C11—C12	1.377 (3)

C6—C1—C2	120.6 (2)	C13—C12—H12	120.4
C6—C1—H1	119.7	C8—C13—C12	121.3 (2)
C2—C1—H1	119.7	C8—C13—H13	119.3
C3—C2—C1	120.5 (2)	C12—C13—H13	119.3
C3—C2—H2	119.7	O1—C14—H14A	109.5
C1—C2—H2	119.7	O1—C14—H14B	109.5
C4—C3—C2	119.5 (2)	H14A—C14—H14B	109.5
C4—C3—H3	120.3	O1—C14—H14C	109.5
C2—C3—H3	120.3	H14A—C14—H14C	109.5
C3—C4—C5	120.3 (2)	H14B—C14—H14C	109.5
C3—C4—H4	119.9	C16—C15—C20	118.2 (2)
C5—C4—H4	119.9	C16—C15—S2	120.83 (19)
C4—C5—C6	120.7 (2)	C20—C15—S2	120.9 (2)
C4—C5—H5	119.6	C15—C16—C17	121.5 (3)
C6—C5—H5	119.6	C15—C16—H16	119.2
C1—C6—C5	118.41 (19)	C17—C16—H16	119.2
C1—C6—C7	119.62 (19)	C18—C17—C16	119.1 (3)
C5—C6—C7	121.96 (19)	C18—C17—H17	120.5
C6—C7—S1	109.22 (13)	C16—C17—H17	120.5
C6—C7—S2	113.90 (14)	C19—C18—O2	115.9 (3)
S1—C7—S2	107.73 (11)	C19—C18—C17	119.3 (3)
C6—C7—H7	108.6	O2—C18—C17	124.8 (3)
S1—C7—H7	108.6	C18—C19—C20	121.4 (3)
S2—C7—H7	108.6	C18—C19—H19	119.3
C9—C8—C13	118.7 (2)	C20—C19—H19	119.3
C9—C8—S1	117.84 (17)	C19—C20—C15	120.5 (3)
C13—C8—S1	123.28 (17)	C19—C20—H20	119.8
C10—C9—C8	120.6 (2)	C15—C20—H20	119.8
C10—C9—H9	119.7	O2—C21—H21A	109.5
C8—C9—H9	119.7	O2—C21—H21B	109.5
C9—C10—C11	120.6 (2)	H21A—C21—H21B	109.5
C9—C10—H10	119.7	O2—C21—H21C	109.5
C11—C10—H10	119.7	H21A—C21—H21C	109.5
O1—C11—C12	125.0 (2)	H21B—C21—H21C	109.5
O1—C11—C10	115.50 (19)	C11—O1—C14	118.12 (18)
C12—C11—C10	119.5 (2)	C18—O2—C21	118.2 (3)
C11—C12—C13	119.2 (2)	C8—S1—C7	102.63 (9)
C11—C12—H12	120.4	C15—S2—C7	100.37 (10)

C6—C1—C2—C3	−0.8 (4)	C20—C15—C16—C17	−1.4 (4)
C1—C2—C3—C4	0.8 (4)	S2—C15—C16—C17	−179.6 (2)
C2—C3—C4—C5	−0.2 (4)	C15—C16—C17—C18	2.0 (5)
C3—C4—C5—C6	−0.5 (4)	C16—C17—C18—C19	−0.9 (5)
C2—C1—C6—C5	0.1 (3)	C16—C17—C18—O2	178.1 (3)
C2—C1—C6—C7	178.7 (2)	O2—C18—C19—C20	−179.7 (3)
C4—C5—C6—C1	0.5 (3)	C17—C18—C19—C20	−0.6 (5)
C4—C5—C6—C7	−178.0 (2)	C18—C19—C20—C15	1.2 (5)
C1—C6—C7—S1	−129.59 (19)	C16—C15—C20—C19	−0.2 (4)
C5—C6—C7—S1	48.9 (2)	S2—C15—C20—C19	178.0 (2)
C1—C6—C7—S2	109.9 (2)	C12—C11—O1—C14	−1.1 (3)
C5—C6—C7—S2	−71.6 (2)	C10—C11—O1—C14	178.5 (2)
C13—C8—C9—C10	−1.1 (3)	C19—C18—O2—C21	−172.7 (3)
S1—C8—C9—C10	174.58 (16)	C17—C18—O2—C21	8.2 (5)
C8—C9—C10—C11	1.5 (3)	C9—C8—S1—C7	131.85 (17)
C9—C10—C11—O1	−179.77 (18)	C13—C8—S1—C7	−52.7 (2)
C9—C10—C11—C12	−0.2 (3)	C6—C7—S1—C8	168.12 (15)
O1—C11—C12—C13	178.0 (2)	S2—C7—S1—C8	−67.69 (13)
C10—C11—C12—C13	−1.5 (3)	C16—C15—S2—C7	−70.3 (2)
C9—C8—C13—C12	−0.6 (3)	C20—C15—S2—C7	111.6 (2)
S1—C8—C13—C12	−176.06 (17)	C6—C7—S2—C15	−73.83 (16)
C11—C12—C13—C8	1.9 (3)	S1—C7—S2—C15	164.86 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2ⁱ	0.93	2.99	3.713 (3)	136
C10—H10···Cg2ⁱⁱ	0.93	2.96	3.610 (2)	128
C21—H21B···Cg1ⁱⁱⁱ	0.96	2.98	3.914 (5)	165

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀O₂S₂
M_r	368.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	21.1506 (15), 5.6114 (3), 17.1219 (11)
β (°)	110.336 (2)
V (Å³)	1905.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.42 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.888, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	12756, 4154, 2725
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.128, 1.02
No. of reflections	4154
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2ⁱ	0.93	2.99	3.713 (3)	136
C10—H10···Cg2ⁱⁱ	0.93	2.96	3.610 (2)	128
C21—H21B···Cg1ⁱⁱⁱ	0.96	2.98	3.914 (5)	165

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

Acknowledgements

RSR thanks CSIR, New Delhi, for funding under the Scientist's Pool Scheme and BIF, University of Hyderabad, for computational resources.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J., Hartley, R. C. & Guthrie, E. (2000). Private communication [refcodes QITPEO, QITPOY, QITPUE and QITQAL (CCDC 149307–CCDC 149310l, respectively)]. CCDC, Union Road, Cambridge, England. 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

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Volume 68| Part 3| March 2012| Page o782

doi:10.1107/S1600536812006320

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Meth­­oxy-4-({[(4-meth­­oxy­phen­yl)­sulfan­yl](phen­yl)meth­yl}sulfan­yl)benzene

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Experimental

Crystal data

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Refinement

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Acknowledgements

References

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