(4-Methyl-phen-yl)[2-(thio-phen-2-ylcarbon-yl)phen-yl]methanone.

The crystal studied of the title compound, C(19)H(14)O(2)S, was an inversion twin with a 0.7 (1):0.3 (1) domain ratio. The central benzene ring makes dihedral angles of 63.31 (9) and 60.86 (9)°, respectively, with the 4-methyl-phenyl and thio-phene rings. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and S⋯π [3.609 (3) Å] inter-actions.

Related literature

For the biological activity of thiophene derivatives, see: Bonini et al. (2005 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For related structures, see: Ranjith et al. (2011 ▶); Dufresne & Skene (2010 ▶).

Experimental

Crystal data

C19H14O2S

M = 306.36

Orthorhombic,

a = 6.8748 (2) Å

b = 13.3291 (4) Å

c = 16.8667 (5) Å

V = 1545.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.948, T max = 0.960

14787 measured reflections

3757 independent reflections

3073 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.154

S = 1.04

3757 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 1564 Friedel pairs

Flack parameter: 0.31 (11)

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, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032478/lx2197sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032478/lx2197Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032478/lx2197Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H14O2S	F(000) = 640
Mr = 306.36	Dx = 1.317 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3758 reflections
a = 6.8748 (2) Å	θ = 2.0–28.2°
b = 13.3291 (4) Å	µ = 0.21 mm−1
c = 16.8667 (5) Å	T = 293 K
V = 1545.58 (8) Å3	Block, white crystalline
Z = 4	0.25 × 0.22 × 0.19 mm

Bruker APEXII CCD area-detector diffractometer	3757 independent reflections
Radiation source: fine-focus sealed tube	3073 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.948, Tmax = 0.960	k = −17→17
14787 measured reflections	l = −21→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0975P)2 + 0.2738P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3757 reflections	Δρmax = 0.84 e Å−3
195 parameters	Δρmin = −0.38 e Å−3
0 restraints	Absolute structure: Flack (1983), 1564 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.31 (11)

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.1784 (5)	0.1736 (3)	0.51343 (18)	0.0572 (8)
H1	0.1693	0.1232	0.5514	0.069*
C2	0.1844 (4)	0.2720 (2)	0.53175 (14)	0.0457 (4)
H2	0.1790	0.2949	0.5838	0.055*
C3	0.2000 (4)	0.3398 (2)	0.46487 (14)	0.0457 (4)
H3	0.2065	0.4095	0.4665	0.055*
C4	0.2035 (4)	0.27597 (17)	0.39395 (13)	0.0364 (5)
C5	0.2388 (3)	0.30681 (16)	0.31244 (13)	0.0336 (5)
C6	0.2404 (4)	0.41697 (16)	0.29365 (12)	0.0335 (5)
C7	0.0825 (4)	0.4758 (2)	0.31315 (15)	0.0438 (6)
H7	−0.0201	0.4487	0.3420	0.053*
C8	0.0768 (5)	0.5760 (2)	0.28959 (17)	0.0536 (7)
H8	−0.0296	0.6157	0.3027	0.064*
C9	0.2277 (5)	0.61580 (19)	0.24717 (16)	0.0544 (7)
H9	0.2235	0.6828	0.2318	0.065*
C10	0.3856 (5)	0.55782 (18)	0.22697 (15)	0.0462 (6)
H10	0.4872	0.5859	0.1981	0.055*
C11	0.3943 (4)	0.45704 (16)	0.24953 (13)	0.0347 (5)
C12	0.5750 (4)	0.39723 (16)	0.23542 (13)	0.0353 (5)
C13	0.6576 (4)	0.39061 (17)	0.15393 (14)	0.0370 (5)
C14	0.5507 (4)	0.41308 (19)	0.08690 (16)	0.0439 (6)
H14	0.4223	0.4340	0.0920	0.053*
C15	0.6323 (5)	0.4049 (2)	0.01220 (15)	0.0525 (7)
H15	0.5573	0.4191	−0.0323	0.063*
C16	0.8252 (5)	0.3755 (2)	0.00285 (15)	0.0519 (7)
C17	0.9301 (5)	0.3518 (2)	0.06999 (17)	0.0543 (7)
H17	1.0586	0.3311	0.0650	0.065*
C18	0.8480 (4)	0.3583 (2)	0.14457 (16)	0.0463 (6)
H18	0.9211	0.3409	0.1889	0.056*
C19	0.9150 (7)	0.3703 (3)	−0.07938 (19)	0.0795 (11)
H19A	0.8544	0.3174	−0.1091	0.119*
H19B	1.0519	0.3572	−0.0748	0.119*
H19C	0.8955	0.4331	−0.1062	0.119*
O1	0.2661 (3)	0.24586 (12)	0.25971 (10)	0.0490 (5)
O2	0.6549 (3)	0.35775 (15)	0.29111 (10)	0.0483 (5)
S1	0.18865 (12)	0.15059 (5)	0.41576 (4)	0.0541 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0465 (16)	0.0748 (19)	0.0504 (16)	0.0050 (15)	0.0071 (13)	0.0224 (14)
C2	0.0344 (9)	0.0752 (12)	0.0275 (7)	0.0050 (9)	0.0001 (7)	0.0048 (8)
C3	0.0344 (9)	0.0752 (12)	0.0275 (7)	0.0050 (9)	0.0001 (7)	0.0048 (8)
C4	0.0339 (12)	0.0403 (11)	0.0351 (11)	−0.0001 (10)	0.0018 (10)	0.0025 (9)
C5	0.0315 (12)	0.0366 (10)	0.0327 (11)	−0.0048 (9)	0.0016 (9)	0.0011 (8)
C6	0.0402 (13)	0.0333 (10)	0.0271 (10)	−0.0022 (9)	−0.0007 (9)	−0.0001 (8)
C7	0.0419 (15)	0.0500 (13)	0.0394 (13)	0.0057 (12)	0.0032 (11)	0.0017 (11)
C8	0.0650 (19)	0.0483 (14)	0.0476 (14)	0.0202 (14)	0.0050 (14)	−0.0002 (12)
C9	0.084 (2)	0.0355 (11)	0.0438 (14)	0.0101 (13)	0.0057 (15)	0.0066 (10)
C10	0.0640 (18)	0.0370 (11)	0.0378 (12)	−0.0016 (12)	0.0100 (12)	0.0066 (10)
C11	0.0431 (13)	0.0346 (10)	0.0265 (10)	−0.0024 (9)	−0.0003 (9)	0.0005 (8)
C12	0.0379 (12)	0.0375 (11)	0.0304 (11)	−0.0072 (9)	0.0002 (9)	0.0015 (9)
C13	0.0448 (14)	0.0351 (10)	0.0311 (11)	−0.0057 (10)	0.0025 (10)	−0.0011 (9)
C14	0.0475 (15)	0.0488 (13)	0.0352 (12)	0.0052 (11)	−0.0001 (11)	0.0020 (11)
C15	0.066 (2)	0.0595 (16)	0.0317 (13)	0.0077 (14)	−0.0008 (12)	0.0007 (11)
C16	0.073 (2)	0.0504 (14)	0.0327 (12)	0.0000 (15)	0.0097 (13)	−0.0047 (10)
C17	0.0479 (15)	0.0639 (17)	0.0512 (16)	0.0054 (14)	0.0120 (13)	−0.0039 (14)
C18	0.0435 (15)	0.0566 (14)	0.0386 (13)	0.0029 (13)	−0.0020 (11)	−0.0016 (11)
C19	0.107 (3)	0.091 (2)	0.0410 (16)	0.014 (2)	0.0258 (18)	−0.0050 (16)
O1	0.0730 (14)	0.0372 (8)	0.0369 (8)	−0.0093 (8)	0.0091 (9)	−0.0068 (7)
O2	0.0488 (11)	0.0629 (11)	0.0333 (9)	0.0044 (9)	0.0005 (8)	0.0104 (8)
S1	0.0591 (4)	0.0503 (4)	0.0529 (4)	0.0018 (3)	0.0079 (3)	0.0118 (3)

C1—C2	1.348 (5)	C10—C11	1.397 (3)
C1—S1	1.677 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.495 (3)
C2—C3	1.449 (4)	C12—O2	1.209 (3)
C2—H2	0.9300	C12—C13	1.490 (3)
C3—C4	1.468 (3)	C13—C14	1.381 (4)
C3—H3	0.9300	C13—C18	1.387 (4)
C4—C5	1.455 (3)	C14—C15	1.383 (4)
C4—S1	1.714 (2)	C14—H14	0.9300
C5—O1	1.219 (3)	C15—C16	1.392 (5)
C5—C6	1.502 (3)	C15—H15	0.9300
C6—C7	1.379 (3)	C16—C17	1.379 (4)
C6—C11	1.399 (3)	C16—C19	1.520 (4)
C7—C8	1.393 (4)	C17—C18	1.381 (4)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.367 (4)	C18—H18	0.9300
C8—H8	0.9300	C19—H19A	0.9600
C9—C10	1.375 (4)	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C2—C1—S1	113.7 (2)	C10—C11—C12	120.3 (2)
C2—C1—H1	123.2	C6—C11—C12	120.61 (19)
S1—C1—H1	123.2	O2—C12—C13	121.2 (2)
C1—C2—C3	115.5 (3)	O2—C12—C11	119.1 (2)
C1—C2—H2	122.2	C13—C12—C11	119.7 (2)
C3—C2—H2	122.2	C14—C13—C18	118.4 (2)
C2—C3—C4	105.9 (2)	C14—C13—C12	122.7 (2)
C2—C3—H3	127.0	C18—C13—C12	118.9 (2)
C4—C3—H3	127.0	C13—C14—C15	120.9 (3)
C5—C4—C3	127.5 (2)	C13—C14—H14	119.6
C5—C4—S1	119.21 (17)	C15—C14—H14	119.6
C3—C4—S1	112.90 (18)	C14—C15—C16	120.8 (3)
O1—C5—C4	121.8 (2)	C14—C15—H15	119.6
O1—C5—C6	119.7 (2)	C16—C15—H15	119.6
C4—C5—C6	118.5 (2)	C17—C16—C15	118.0 (3)
C7—C6—C11	120.3 (2)	C17—C16—C19	121.8 (3)
C7—C6—C5	120.0 (2)	C15—C16—C19	120.2 (3)
C11—C6—C5	119.4 (2)	C16—C17—C18	121.3 (3)
C6—C7—C8	119.9 (3)	C16—C17—H17	119.3
C6—C7—H7	120.0	C18—C17—H17	119.3
C8—C7—H7	120.0	C17—C18—C13	120.6 (3)
C9—C8—C7	120.0 (3)	C17—C18—H18	119.7
C9—C8—H8	120.0	C13—C18—H18	119.7
C7—C8—H8	120.0	C16—C19—H19A	109.5
C8—C9—C10	120.7 (2)	C16—C19—H19B	109.5
C8—C9—H9	119.7	H19A—C19—H19B	109.5
C10—C9—H9	119.7	C16—C19—H19C	109.5
C9—C10—C11	120.4 (3)	H19A—C19—H19C	109.5
C9—C10—H10	119.8	H19B—C19—H19C	109.5
C11—C10—H10	119.8	C1—S1—C4	92.00 (14)
C10—C11—C6	118.6 (2)
S1—C1—C2—C3	−0.4 (4)	C5—C6—C11—C12	−12.7 (3)
C1—C2—C3—C4	0.3 (3)	C10—C11—C12—O2	122.4 (3)
C2—C3—C4—C5	−172.8 (2)	C6—C11—C12—O2	−50.0 (3)
C2—C3—C4—S1	0.0 (3)	C10—C11—C12—C13	−55.2 (3)
C3—C4—C5—O1	169.2 (2)	C6—C11—C12—C13	132.4 (2)
S1—C4—C5—O1	−3.1 (3)	O2—C12—C13—C14	164.1 (2)
C3—C4—C5—C6	−11.0 (4)	C11—C12—C13—C14	−18.3 (3)
S1—C4—C5—C6	176.69 (18)	O2—C12—C13—C18	−14.3 (3)
O1—C5—C6—C7	124.5 (3)	C11—C12—C13—C18	163.3 (2)
C4—C5—C6—C7	−55.3 (3)	C18—C13—C14—C15	−0.8 (4)
O1—C5—C6—C11	−49.3 (3)	C12—C13—C14—C15	−179.3 (2)
C4—C5—C6—C11	131.0 (2)	C13—C14—C15—C16	−1.2 (4)
C11—C6—C7—C8	−0.7 (4)	C14—C15—C16—C17	2.0 (4)
C5—C6—C7—C8	−174.4 (2)	C14—C15—C16—C19	−177.8 (3)
C6—C7—C8—C9	0.0 (4)	C15—C16—C17—C18	−0.9 (5)
C7—C8—C9—C10	0.3 (5)	C19—C16—C17—C18	178.9 (3)
C8—C9—C10—C11	0.0 (4)	C16—C17—C18—C13	−1.1 (5)
C9—C10—C11—C6	−0.7 (4)	C14—C13—C18—C17	1.9 (4)
C9—C10—C11—C12	−173.2 (3)	C12—C13—C18—C17	−179.6 (3)
C7—C6—C11—C10	1.0 (3)	C2—C1—S1—C4	0.3 (3)
C5—C6—C11—C10	174.8 (2)	C5—C4—S1—C1	173.2 (2)
C7—C6—C11—C12	173.5 (2)	C3—C4—S1—C1	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.93	2.51	3.386 (3)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2i	0.93	2.51	3.386 (3)	158

Symmetry code: (i) .