1,3-Bis(phenyl­sufanylmeth­yl)benzene

Stewart, C.A.; Dickie, D.A.; Kemp, R.A.

doi:10.1107/S1600536810005775

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o677-o678

doi:10.1107/S1600536810005775

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1,3-Bis(phenylsufanylmethyl)benzene

Constantine A. Stewart,^a Diane A. Dickie ^b and Richard A. Kemp ^b ^*

^aAdvanced Materials Laboratory, Sandia National Laboratories, 1001 University Blvd SE, Albuquerque, NM, 87106, USA, and ^bDepartment of Chemistry and Chemical Biology, MSC03 2060, 1 University of New Mexico, Albuquerque, NM, 87131, USA
^*Correspondence e-mail: rakemp@unm.edu

(Received 11 December 2009; accepted 11 February 2010; online 20 February 2010)

The complete molecule of the title compound, C₂₀H₁₈S₂, is generated by crystallographic mirror symmetry, with two C atoms lying on the mirror plane. All of the independent atoms are contained within two planes defined by the thiophenyl rings (C₆S) and the central phenyl ring with the methylene bridge; the r.m.s deviations of these planes are 0.012 and 0.025 Å, respectively. The two planes are almost perpendicular to one another at a dihedral angle of 80.24 (10)°. Intermolecular C—H—π interactions are present in the crystal structure.

Related literature

For the use of the title compound as a ligand, see: Bu et al. (2002 ); Romero et al. (1996 ); Loeb & Wisner (1998 ); Kruithof et al. (2008 ); Bergholdt et al. (1998 ); Kobayashi et al. (2000 ). For related organic molecules, see: Cervantes et al. (2006 ); Sillanpää et al. (1994 ); Arroyo et al. (2003 ).

Experimental

Crystal data

C₂₀H₁₈S₂
M_r = 322.46
Orthorhombic, C m c 2₁
a = 32.072 (2) Å
b = 7.6053 (5) Å
c = 6.8224 (5) Å
V = 1664.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 228 K
0.76 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.797, T_max = 0.970
14404 measured reflections
1689 independent reflections
1417 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.12
1689 reflections
103 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 738 Friedel pairs
Flack parameter: 0.05 (12)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C3′/C2′ and C6–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg1ⁱ	0.94	2.69	3.57 (5)	155
C1—H1A⋯Cg1ⁱⁱ	0.94	2.69	3.57 (5)	155
C7—H7A⋯Cg2ⁱⁱⁱ	0.94	2.85	3.67 (6)	147
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: XL in SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: publCIF (McMahon & Westrip, 2008 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810005775/fb2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005775/fb2176Isup2.hkl

checkCIF report

Comment top

The title compound, 1,3-bis(phenylthiomethyl)benzene, belongs to a class of transition metal ligands known as SCS-pincer ligands because of their tendency to act as tridentate chelators through one carbon and two sulfur atoms. The plane containing the thiophenyl ring is rotated almost perpendicular to the plane of the central phenyl ring, at an angle of 80.24 (10)°. This is comparable to the para-fluoro (Cervantes et al., 2006) and ortho-ethylester (Sillanpää et al., 1994) derivatives, whose interplanar angles measure 78.13 (10) and 87.66 (10)° respectively. Surprisingly, in the only other structurally characterized derivative, the perfluorinated 1,3-bis(pentafluorophenylthiomethyl)benzene (Arroyo et al., 2003), the rings are nearly co-planar with angles of 8.93 (10) and 10.85 (9)° between the central phenyl and the two independent flanking perfluoro rings. In both the title compound and the para-fluoro derivative, the flanking aryl rings are oriented on the same face of the central ring.

Although the structure of the title compound has not been previously determined, several of its metal complexes are known. Two types of coordination were observered in structurally characterized metal complexes. In the presence of silver perchlorate (Bu et al., 2002) or silver nitrate (Romero et al., 1996), the title compound acts as a bridging ligand through sulfur. In these two complexes, the flanking aryls remain on the same face of the central ring. With Pd (Loeb & Wisner, 1998), Pt (Kruithof et al., 2008) and Te (Bergholdt et al., 1998; Kobayashi et al., 2000) the much more common trihapto-SCS "pincer"-type coordination is observed and the thiophenyl rings rotate to opposite faces of the central phenyl. In all seven examples, the mirror plane present within the free ligand has been broken. The nearly perpendicular orientation of the planes of flanking aryls and the central phenyl (80.24 (10)°) is maintained in each of the Te (Bergholdt et al., 1998; Kobayashi et al., 2000) and Pt (Kruithof et al., 2008) complexes, which have interplanar angles ranging from 77.8 (3) to 89.7 (3)°. In contrast, the interplanar angles in the Ag and Pd complexes cover a much wider range within and across the molecules, measuring 44.1 (6) and 65.5 (6)° in the AgClO₄ based-complex (Bu et al., 2002), 44.5 (3) and 70.4 (2)° for AgNO₃ (Romero et al., 1996), and 40.3 (12) and 88.8 (13)° at one end of the Pd-rotaxane and 41.9 (12) and 89.4 (13)° at the other (Loeb & Wisner, 1998).

Related literature top

For the use of the title compound as a ligand, see: Bu et al. (2002); Romero et al. (1996); Loeb & Wisner (1998); Kruithof et al. (2008); Bergholdt et al. (1998); Kobayashi et al. (2000). For related organic molecules, see: Cervantes et al. (2006); Sillanpää et al. (1994); Arroyo et al. (2003).

Experimental top

1,3-Bis((phenylthio)methyl)benzene was synthesized according to the literature method (Romero, et al. 1996). To grow crystals, a saturated solution of 1,3-bis((phenylthio)methyl)benzene was prepared in hot pentane. An aliquot of this saturated solution was transferred to a 20 ml vial, which was then tightly capped. The vial was placed in a bath of hot water and allowed to slowly cool to room temperature. Colorless, needle-like crystals of up to 10 mm in length formed over approximately 30 minutes. The solvent was then decanted and the crystals allowed to air dry. Several needles of ca. 1 mm in length were placed in a melting point capillary with an internal diameter 0.5 mm and the melting point was determined to be 84 - 86 °C.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008); program(s) used to refine structure: XL in SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (McMahon & Westrip, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound showing full numbering scheme. The displacement ellipsoids are shown at the 50% probability level.

1,3-Bis(phenylsufanylmethyl)benzene top

Crystal data top

C₂₀H₁₈S₂	D_x = 1.287 Mg m⁻³
M_r = 322.46	Melting point = 357–359 K
Orthorhombic, Cmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 8194 reflections
a = 32.072 (2) Å	θ = 2.8–28.1°
b = 7.6053 (5) Å	µ = 0.31 mm⁻¹
c = 6.8224 (5) Å	T = 228 K
V = 1664.1 (2) Å³	Needle, colourless
Z = 4	0.76 × 0.15 × 0.10 mm
F(000) = 680

Data collection top

Bruker APEXII CCD area-detector diffractometer	1689 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 26.4°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −40→40
T_min = 0.797, T_max = 0.970	k = −9→9
14404 measured reflections	l = −8→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0408P)² + 0.6358P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
1689 reflections	Δρ_max = 0.27 e Å⁻³
103 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 736 Friedel pairs
38 constraints	Absolute structure parameter: 0.05 (12)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₁₈S₂	V = 1664.1 (2) Å³
M_r = 322.46	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 32.072 (2) Å	µ = 0.31 mm⁻¹
b = 7.6053 (5) Å	T = 228 K
c = 6.8224 (5) Å	0.76 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1689 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1417 reflections with I > 2σ(I)
T_min = 0.797, T_max = 0.970	R_int = 0.052
14404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.27 e Å⁻³
S = 1.12	Δρ_min = −0.31 e Å⁻³
1689 reflections	Absolute structure: Flack (1983), 736 Friedel pairs
103 parameters	Absolute structure parameter: 0.05 (12)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.415866 (15)	0.21909 (7)	0.49099 (13)	0.03480 (17)
C1	0.5000	0.3639 (4)	0.7139 (5)	0.0295 (7)
H1A	0.5000	0.4312	0.5984	0.035*
C2	0.46220 (7)	0.3148 (3)	0.7983 (4)	0.0295 (5)
C3	0.46271 (7)	0.2166 (3)	0.9699 (5)	0.0362 (6)
H3A	0.4374	0.1836	1.0290	0.043*
C4	0.5000	0.1671 (4)	1.0546 (6)	0.0406 (9)
H4A	0.5000	0.0996	1.1700	0.049*
C5	0.42152 (7)	0.3621 (3)	0.7015 (4)	0.0343 (6)
H5A	0.4218	0.4855	0.6601	0.041*
H5B	0.3983	0.3448	0.7928	0.041*
C6	0.36379 (7)	0.2480 (3)	0.4147 (4)	0.0313 (5)
C7	0.33665 (6)	0.3748 (3)	0.4885 (5)	0.0344 (5)
H7A	0.3459	0.4547	0.5843	0.041*
C8	0.29608 (8)	0.3827 (3)	0.4201 (4)	0.0400 (6)
H8A	0.2779	0.4681	0.4710	0.048*
C9	0.28185 (8)	0.2686 (3)	0.2796 (4)	0.0449 (7)
H9A	0.2541	0.2750	0.2353	0.054*
C10	0.30905 (8)	0.1432 (4)	0.2032 (4)	0.0467 (7)
H10A	0.2998	0.0651	0.1058	0.056*
C11	0.34957 (8)	0.1333 (3)	0.2704 (4)	0.0401 (6)
H11A	0.3677	0.0483	0.2183	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0321 (3)	0.0375 (3)	0.0348 (3)	0.0052 (2)	0.0004 (3)	−0.0071 (4)
C1	0.0353 (17)	0.0270 (15)	0.0264 (19)	0.000	0.000	0.0012 (14)
C2	0.0326 (12)	0.0268 (10)	0.0290 (13)	0.0000 (9)	0.0007 (10)	−0.0049 (11)
C3	0.0406 (12)	0.0326 (10)	0.0356 (15)	−0.0048 (9)	0.0095 (14)	−0.0008 (13)
C4	0.058 (2)	0.0348 (17)	0.029 (2)	0.000	0.000	0.0085 (15)
C5	0.0304 (11)	0.0341 (12)	0.0382 (15)	0.0018 (10)	0.0014 (11)	−0.0071 (11)
C6	0.0316 (12)	0.0328 (11)	0.0295 (13)	−0.0041 (9)	0.0021 (9)	0.0027 (10)
C7	0.0321 (10)	0.0384 (11)	0.0327 (13)	−0.0010 (8)	0.0007 (14)	−0.0038 (15)
C8	0.0355 (13)	0.0476 (14)	0.0369 (15)	0.0035 (11)	0.0043 (11)	−0.0001 (11)
C9	0.0335 (13)	0.0581 (15)	0.0430 (18)	−0.0060 (11)	−0.0051 (12)	0.0049 (15)
C10	0.0478 (16)	0.0509 (16)	0.0413 (18)	−0.0095 (12)	−0.0065 (13)	−0.0095 (13)
C11	0.0446 (14)	0.0375 (13)	0.0381 (16)	0.0002 (11)	0.0010 (12)	−0.0101 (12)

Geometric parameters (Å, º) top

S1—C6	1.763 (2)	C5—H5B	0.9800
S1—C5	1.811 (2)	C6—C11	1.392 (3)
C1—C2ⁱ	1.393 (3)	C6—C7	1.393 (3)
C1—C2	1.393 (3)	C7—C8	1.384 (3)
C1—H1A	0.9400	C7—H7A	0.9400
C2—C3	1.388 (4)	C8—C9	1.371 (4)
C2—C5	1.506 (3)	C8—H8A	0.9400
C3—C4	1.381 (3)	C9—C10	1.394 (4)
C3—H3A	0.9400	C9—H9A	0.9400
C4—C3ⁱ	1.381 (3)	C10—C11	1.380 (3)
C4—H4A	0.9400	C10—H10A	0.9400
C5—H5A	0.9800	C11—H11A	0.9400

C6—S1—C5	104.72 (11)	C11—C6—C7	119.0 (2)
C2ⁱ—C1—C2	121.0 (3)	C11—C6—S1	116.16 (18)
C2ⁱ—C1—H1A	119.5	C7—C6—S1	124.85 (19)
C2—C1—H1A	119.5	C8—C7—C6	119.7 (2)
C3—C2—C1	118.8 (2)	C8—C7—H7A	120.2
C3—C2—C5	120.57 (19)	C6—C7—H7A	120.2
C1—C2—C5	120.5 (2)	C9—C8—C7	121.4 (2)
C4—C3—C2	120.6 (2)	C9—C8—H8A	119.3
C4—C3—H3A	119.7	C7—C8—H8A	119.3
C2—C3—H3A	119.7	C8—C9—C10	119.1 (2)
C3—C4—C3ⁱ	120.1 (4)	C8—C9—H9A	120.5
C3—C4—H4A	120.0	C10—C9—H9A	120.5
C3ⁱ—C4—H4A	120.0	C11—C10—C9	120.2 (2)
C2—C5—S1	106.92 (15)	C11—C10—H10A	119.9
C2—C5—H5A	110.3	C9—C10—H10A	119.9
S1—C5—H5A	110.3	C10—C11—C6	120.6 (2)
C2—C5—H5B	110.3	C10—C11—H11A	119.7
S1—C5—H5B	110.3	C6—C11—H11A	119.7
H5A—C5—H5B	108.6

C2ⁱ—C1—C2—C3	0.6 (4)	C5—S1—C6—C7	8.5 (2)
C2ⁱ—C1—C2—C5	−177.45 (19)	C11—C6—C7—C8	1.1 (4)
C1—C2—C3—C4	−0.6 (4)	S1—C6—C7—C8	−178.7 (2)
C5—C2—C3—C4	177.4 (2)	C6—C7—C8—C9	−0.4 (4)
C2—C3—C4—C3ⁱ	0.7 (5)	C7—C8—C9—C10	−0.5 (4)
C3—C2—C5—S1	−104.0 (2)	C8—C9—C10—C11	0.7 (4)
C1—C2—C5—S1	74.0 (2)	C9—C10—C11—C6	0.0 (4)
C6—S1—C5—C2	168.24 (15)	C7—C6—C11—C10	−0.9 (4)
C5—S1—C6—C11	−171.28 (19)	S1—C6—C11—C10	178.9 (2)

Symmetry code: (i) −x+1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C4/C3'/C2' and C6–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg1ⁱⁱ	0.94	2.69	3.57 (5)	155
C1—H1A···Cg1ⁱⁱⁱ	0.94	2.69	3.57 (5)	155
C7—H7A···Cg2^iv	0.94	2.85	3.67 (6)	147

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈S₂
M_r	322.46
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	228
a, b, c (Å)	32.072 (2), 7.6053 (5), 6.8224 (5)
V (Å³)	1664.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.76 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.797, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	14404, 1689, 1417
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.12
No. of reflections	1689
No. of parameters	103
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31
Absolute structure	Flack (1983), 736 Friedel pairs
Absolute structure parameter	0.05 (12)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XS in SHELXTL (Sheldrick, 2008), XL in SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (McMahon & Westrip, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C4/C3'/C2' and C6–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg1ⁱ	0.94	2.69	3.57 (5)	154.6
C1—H1A···Cg1ⁱⁱ	0.94	2.69	3.57 (5)	154.6
C7—H7A···Cg2ⁱⁱⁱ	0.94	2.85	3.67 (6)	146.7

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

Acknowledgements

Funding was provided by a Department of Energy grant (DE–FG02-06ER15765 to RAK) and the Sandia LDRD progam (105932). Sandia is a multiprogram laboratory operated by Sandia Corporation, a Lockheed Martin Company, for the United States Department of Energy under Contract No. DE–AC04-94 A L85000. The diffractometer was purchased via a National Science Foundation CRIF:MU award to the University of New Mexico (CHE-0443580).

References

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