(3,4-Dimeth-oxy-phen-yl)[2-(thio-phen-2-ylcarbon-yl)phen-yl]methanone.

In the title compound, C(20)H(16)O(4)S, the thiophene ring makes dihedral angles of 72.9 (2) and 60.5 (2)°, respectively, with the dimethoxy benzene and phenyl rings. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a C(9) chain along the b axis. The S and C atoms of the thio-phene ring are disordered over two sets of sites [site occupancies = 0.675 (3) and 0.325 (3)]. A short inter-molecular S⋯O contact [3.084 (2) Å] is observed in the crystal structure, which also features C-H⋯π inter-actions.

Related literature

For background to thio­phene derivatives and their biological activity, see: Bonini et al. (2005 ▶); Khan et al. (2009 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For related structures, see: Asiri et al. (2010 ▶); Aslam et al. (2011 ▶).

Experimental

Crystal data

C20H16O4S

M = 352.40

Orthorhombic,

a = 15.7324 (6) Å

b = 10.7988 (5) Å

c = 20.4877 (11) Å

V = 3480.7 (3) Å3

Z = 8

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 = 0.950, T max = 0.961

22015 measured reflections

4469 independent reflections

2968 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.03

4469 reflections

236 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536812037336/bt5963sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037336/bt5963Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037336/bt5963Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812037336/bt5963Isup4.cml

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

C20H16O4S	F(000) = 1472
Mr = 352.40	Dx = 1.345 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4469 reflections
a = 15.7324 (6) Å	θ = 2.4–28.6°
b = 10.7988 (5) Å	µ = 0.21 mm−1
c = 20.4877 (11) Å	T = 293 K
V = 3480.7 (3) Å3	Block, white crystalline
Z = 8	0.25 × 0.22 × 0.19 mm

Bruker APEXII CCD area-detector diffractometer	4469 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 28.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→12
Tmin = 0.950, Tmax = 0.961	k = −14→13
22015 measured reflections	l = −26→27

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) = 0.107	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.6807P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4469 reflections	Δρmax = 0.19 e Å−3
236 parameters	Δρmin = −0.20 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (4)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.07420 (12)	0.29212 (17)	0.52465 (9)	0.0702 (5)
H1A	0.0927	0.2750	0.5684	0.105*
H1B	0.0939	0.2278	0.4960	0.105*
H1C	0.0132	0.2953	0.5235	0.105*
C2	0.08842 (9)	0.44770 (14)	0.44314 (7)	0.0447 (3)
C3	0.03902 (9)	0.38431 (14)	0.39886 (7)	0.0487 (4)
H3	0.0165	0.3075	0.4099	0.058*
C4	0.02285 (9)	0.43475 (14)	0.33805 (7)	0.0471 (3)
H4	−0.0110	0.3917	0.3086	0.056*
C5	0.05654 (8)	0.54875 (13)	0.32047 (7)	0.0419 (3)
C6	0.10764 (8)	0.61269 (13)	0.36538 (7)	0.0432 (3)
H6	0.1313	0.6885	0.3539	0.052*
C7	0.12280 (9)	0.56397 (14)	0.42603 (7)	0.0448 (3)
C8	0.20416 (12)	0.73733 (16)	0.46082 (9)	0.0669 (5)
H8A	0.2364	0.7649	0.4979	0.100*
H8B	0.1584	0.7942	0.4528	0.100*
H8C	0.2404	0.7337	0.4232	0.100*
C10	−0.02731 (9)	0.55919 (13)	0.21288 (7)	0.0432 (3)
C11	−0.10859 (9)	0.55142 (16)	0.23926 (9)	0.0567 (4)
H11	−0.1164	0.5629	0.2838	0.068*
C12	−0.17778 (10)	0.52680 (18)	0.19982 (10)	0.0672 (5)
H12	−0.2320	0.5229	0.2178	0.081*
C13	−0.16671 (11)	0.50815 (17)	0.13424 (10)	0.0664 (5)
H13	−0.2134	0.4912	0.1079	0.080*
C14	−0.08662 (10)	0.51440 (15)	0.10716 (8)	0.0567 (4)
H14	−0.0796	0.5011	0.0626	0.068*
C15	−0.01622 (9)	0.54042 (13)	0.14591 (7)	0.0443 (3)
C16	0.06748 (10)	0.54873 (14)	0.11162 (7)	0.0496 (4)
C17	0.13814 (9)	0.47030 (14)	0.13224 (7)	0.0464 (3)
C9	0.04505 (9)	0.60239 (13)	0.25482 (7)	0.0436 (3)
O1	0.10795 (7)	0.40790 (11)	0.50401 (5)	0.0615 (3)
O2	0.17058 (8)	0.61823 (10)	0.47356 (5)	0.0634 (3)
O3	0.09238 (7)	0.68272 (10)	0.23367 (5)	0.0606 (3)
O4	0.07382 (8)	0.61470 (13)	0.06358 (6)	0.0795 (4)
C19	0.22592 (12)	0.31667 (19)	0.17820 (10)	0.0741 (5)
H19	0.2419	0.2511	0.2050	0.089*
C20	0.27476 (11)	0.37328 (19)	0.13340 (10)	0.0747 (6)
H20	0.3309	0.3501	0.1263	0.090*
S1	0.22947 (5)	0.48657 (9)	0.09150 (7)	0.0691 (3)	0.675 (3)
C18	0.1412 (3)	0.3789 (4)	0.1768 (2)	0.0592 (17)*	0.675 (3)
H18	0.0959	0.3571	0.2036	0.071*	0.675 (3)
S1'	0.13250 (13)	0.3528 (2)	0.18931 (11)	0.0487 (5)	0.325 (3)
C18'	0.2189 (6)	0.4727 (13)	0.1078 (7)	0.160 (9)*	0.325 (3)
H18'	0.2373	0.5316	0.0778	0.192*	0.325 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0799 (12)	0.0676 (11)	0.0631 (11)	0.0014 (9)	0.0013 (9)	0.0211 (9)
C2	0.0434 (7)	0.0473 (8)	0.0434 (8)	0.0063 (6)	0.0002 (6)	0.0017 (6)
C3	0.0491 (8)	0.0439 (8)	0.0530 (9)	−0.0046 (6)	−0.0002 (7)	0.0035 (7)
C4	0.0457 (8)	0.0474 (8)	0.0481 (8)	−0.0060 (6)	−0.0023 (6)	−0.0029 (7)
C5	0.0387 (7)	0.0450 (8)	0.0420 (7)	0.0002 (6)	0.0029 (6)	−0.0017 (6)
C6	0.0409 (7)	0.0412 (7)	0.0475 (8)	−0.0024 (6)	0.0012 (6)	−0.0024 (6)
C7	0.0410 (7)	0.0457 (8)	0.0477 (8)	0.0011 (6)	−0.0031 (6)	−0.0060 (7)
C8	0.0731 (11)	0.0563 (10)	0.0713 (11)	−0.0111 (9)	−0.0122 (9)	−0.0112 (9)
C10	0.0414 (7)	0.0428 (8)	0.0455 (8)	0.0021 (6)	0.0003 (6)	0.0048 (6)
C11	0.0468 (8)	0.0665 (10)	0.0567 (9)	0.0039 (7)	0.0043 (7)	0.0047 (8)
C12	0.0392 (9)	0.0766 (12)	0.0860 (13)	0.0023 (8)	−0.0010 (8)	0.0088 (10)
C13	0.0522 (10)	0.0669 (11)	0.0801 (13)	0.0023 (8)	−0.0214 (9)	0.0003 (10)
C14	0.0617 (10)	0.0565 (10)	0.0520 (9)	0.0055 (8)	−0.0131 (8)	−0.0006 (8)
C15	0.0479 (8)	0.0403 (7)	0.0448 (8)	0.0039 (6)	−0.0027 (6)	0.0035 (6)
C16	0.0590 (9)	0.0486 (8)	0.0411 (8)	0.0023 (7)	0.0036 (7)	0.0010 (7)
C17	0.0464 (8)	0.0490 (8)	0.0438 (8)	−0.0003 (6)	0.0065 (6)	−0.0059 (7)
C9	0.0436 (7)	0.0431 (7)	0.0441 (8)	0.0003 (6)	0.0049 (6)	−0.0030 (6)
O1	0.0726 (7)	0.0614 (7)	0.0506 (6)	−0.0004 (6)	−0.0104 (5)	0.0102 (5)
O2	0.0760 (8)	0.0576 (7)	0.0565 (7)	−0.0122 (6)	−0.0208 (6)	−0.0018 (5)
O3	0.0676 (7)	0.0615 (7)	0.0527 (6)	−0.0207 (6)	0.0014 (5)	0.0064 (5)
O4	0.0883 (9)	0.0898 (9)	0.0605 (7)	0.0172 (7)	0.0181 (7)	0.0303 (7)
C19	0.0794 (13)	0.0703 (12)	0.0724 (12)	0.0139 (10)	−0.0122 (10)	−0.0096 (10)
C20	0.0453 (9)	0.0834 (13)	0.0954 (15)	0.0117 (9)	0.0010 (10)	−0.0217 (12)
S1	0.0501 (4)	0.0695 (5)	0.0876 (6)	0.0022 (3)	0.0239 (4)	−0.0130 (4)
S1'	0.0502 (9)	0.0473 (9)	0.0485 (9)	0.0120 (7)	0.0026 (7)	0.0027 (8)

C1—O1	1.423 (2)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.370 (3)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.378 (2)
C2—O1	1.3544 (17)	C13—H13	0.9300
C2—C3	1.377 (2)	C14—C15	1.391 (2)
C2—C7	1.411 (2)	C14—H14	0.9300
C3—C4	1.383 (2)	C15—C16	1.495 (2)
C3—H3	0.9300	C16—O4	1.2191 (18)
C4—C5	1.388 (2)	C16—C17	1.460 (2)
C4—H4	0.9300	C17—C18	1.345 (4)
C5—C6	1.4034 (19)	C17—C18'	1.366 (9)
C5—C9	1.4756 (19)	C17—S1	1.6709 (17)
C6—C7	1.370 (2)	C17—S1'	1.728 (3)
C6—H6	0.9300	C9—O3	1.2225 (16)
C7—O2	1.3625 (17)	C19—C20	1.344 (3)
C8—O2	1.415 (2)	C19—C18	1.493 (5)
C8—H8A	0.9600	C19—S1'	1.538 (3)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—C18'	1.483 (10)
C10—C11	1.391 (2)	C20—S1	1.656 (2)
C10—C15	1.3979 (19)	C20—H20	0.9300
C10—C9	1.501 (2)	C18—H18	0.9300
C11—C12	1.382 (2)	C18'—H18'	0.9300
O1—C1—H1A	109.5	C13—C14—H14	119.7
O1—C1—H1B	109.5	C15—C14—H14	119.7
H1A—C1—H1B	109.5	C14—C15—C10	119.35 (14)
O1—C1—H1C	109.5	C14—C15—C16	116.43 (13)
H1A—C1—H1C	109.5	C10—C15—C16	124.22 (13)
H1B—C1—H1C	109.5	O4—C16—C17	120.68 (14)
O1—C2—C3	125.24 (14)	O4—C16—C15	119.11 (14)
O1—C2—C7	115.09 (13)	C17—C16—C15	119.99 (13)
C3—C2—C7	119.67 (13)	C18—C17—C18'	103.3 (6)
C2—C3—C4	120.10 (14)	C18—C17—C16	130.5 (2)
C2—C3—H3	120.0	C18'—C17—C16	126.3 (5)
C4—C3—H3	120.0	C18—C17—S1	112.7 (2)
C3—C4—C5	120.85 (13)	C18'—C17—S1	10.0 (5)
C3—C4—H4	119.6	C16—C17—S1	116.69 (11)
C5—C4—H4	119.6	C18—C17—S1'	5.0 (3)
C4—C5—C6	119.02 (13)	C18'—C17—S1'	108.0 (5)
C4—C5—C9	122.54 (13)	C16—C17—S1'	125.64 (12)
C6—C5—C9	118.33 (12)	S1—C17—S1'	117.35 (12)
C7—C6—C5	120.35 (13)	O3—C9—C5	121.81 (13)
C7—C6—H6	119.8	O3—C9—C10	118.66 (13)
C5—C6—H6	119.8	C5—C9—C10	119.52 (12)
O2—C7—C6	125.38 (13)	C2—O1—C1	117.90 (13)
O2—C7—C2	114.62 (13)	C7—O2—C8	117.72 (12)
C6—C7—C2	120.00 (13)	C20—C19—C18	107.0 (2)
O2—C8—H8A	109.5	C20—C19—S1'	122.1 (2)
O2—C8—H8B	109.5	C18—C19—S1'	15.25 (19)
H8A—C8—H8B	109.5	C20—C19—H19	126.5
O2—C8—H8C	109.5	C18—C19—H19	126.5
H8A—C8—H8C	109.5	S1'—C19—H19	111.3
H8B—C8—H8C	109.5	C19—C20—C18'	103.4 (4)
C11—C10—C15	119.17 (14)	C19—C20—S1	116.37 (14)
C11—C10—C9	119.58 (13)	C18'—C20—S1	13.3 (4)
C15—C10—C9	120.83 (13)	C19—C20—H20	121.8
C12—C11—C10	120.58 (16)	C18'—C20—H20	134.6
C12—C11—H11	119.7	S1—C20—H20	121.8
C10—C11—H11	119.7	C20—S1—C17	91.91 (11)
C13—C12—C11	120.11 (16)	C17—C18—C19	112.0 (3)
C13—C12—H12	119.9	C17—C18—H18	124.0
C11—C12—H12	119.9	C19—C18—H18	124.0
C12—C13—C14	120.26 (16)	C19—S1'—C17	92.13 (16)
C12—C13—H13	119.9	C17—C18'—C20	114.1 (8)
C14—C13—H13	119.9	C17—C18'—H18'	123.0
C13—C14—C15	120.52 (16)	C20—C18'—H18'	123.0
O1—C2—C3—C4	179.55 (13)	C4—C5—C9—C10	21.6 (2)
C7—C2—C3—C4	−0.3 (2)	C6—C5—C9—C10	−162.15 (12)
C2—C3—C4—C5	0.6 (2)	C11—C10—C9—O3	−131.30 (15)
C3—C4—C5—C6	0.1 (2)	C15—C10—C9—O3	41.2 (2)
C3—C4—C5—C9	176.30 (13)	C11—C10—C9—C5	47.76 (19)
C4—C5—C6—C7	−1.1 (2)	C15—C10—C9—C5	−139.72 (14)
C9—C5—C6—C7	−177.44 (12)	C3—C2—O1—C1	−0.8 (2)
C5—C6—C7—O2	−179.37 (13)	C7—C2—O1—C1	179.09 (14)
C5—C6—C7—C2	1.3 (2)	C6—C7—O2—C8	3.2 (2)
O1—C2—C7—O2	0.10 (18)	C2—C7—O2—C8	−177.42 (14)
C3—C2—C7—O2	179.99 (13)	C18—C19—C20—C18'	2.3 (7)
O1—C2—C7—C6	179.46 (12)	S1'—C19—C20—C18'	4.5 (7)
C3—C2—C7—C6	−0.6 (2)	C18—C19—C20—S1	−1.0 (3)
C15—C10—C11—C12	−0.7 (2)	S1'—C19—C20—S1	1.2 (3)
C9—C10—C11—C12	171.96 (15)	C19—C20—S1—C17	1.00 (17)
C10—C11—C12—C13	0.9 (3)	C18'—C20—S1—C17	−13 (3)
C11—C12—C13—C14	−0.3 (3)	C18—C17—S1—C20	−0.7 (3)
C12—C13—C14—C15	−0.4 (3)	C18'—C17—S1—C20	19 (4)
C13—C14—C15—C10	0.5 (2)	C16—C17—S1—C20	−176.59 (13)
C13—C14—C15—C16	−178.31 (15)	S1'—C17—S1—C20	−2.63 (14)
C11—C10—C15—C14	0.0 (2)	C18'—C17—C18—C19	−3.2 (8)
C9—C10—C15—C14	−172.56 (13)	C16—C17—C18—C19	175.46 (19)
C11—C10—C15—C16	178.76 (14)	S1—C17—C18—C19	0.3 (4)
C9—C10—C15—C16	6.2 (2)	S1'—C17—C18—C19	160 (3)
C14—C15—C16—O4	50.8 (2)	C20—C19—C18—C17	0.4 (4)
C10—C15—C16—O4	−127.95 (17)	S1'—C19—C18—C17	−172.7 (12)
C14—C15—C16—C17	−123.81 (15)	C20—C19—S1'—C17	−2.5 (2)
C10—C15—C16—C17	57.4 (2)	C18—C19—S1'—C17	5.3 (9)
O4—C16—C17—C18	−169.2 (3)	C18—C17—S1'—C19	−18 (3)
C15—C16—C17—C18	5.4 (4)	C18'—C17—S1'—C19	−0.7 (8)
O4—C16—C17—C18'	9.2 (9)	C16—C17—S1'—C19	176.50 (15)
C15—C16—C17—C18'	−176.3 (9)	S1—C17—S1'—C19	3.15 (16)
O4—C16—C17—S1	5.9 (2)	C18—C17—C18'—C20	4.8 (13)
C15—C16—C17—S1	−179.57 (11)	C16—C17—C18'—C20	−173.9 (6)
O4—C16—C17—S1'	−167.53 (16)	S1—C17—C18'—C20	−157 (5)
C15—C16—C17—S1'	7.0 (2)	S1'—C17—C18'—C20	3.3 (13)
C4—C5—C9—O3	−159.37 (14)	C19—C20—C18'—C17	−4.7 (13)
C6—C5—C9—O3	16.9 (2)	S1—C20—C18'—C17	162 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.93	2.58	3.496 (2)	169
C1—H1A···Cg2ii	0.96	2.99	3.799 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C17/C19/C20/S1′/C18′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.93	2.58	3.496 (2)	169
C1—H1A⋯Cg2ii	0.96	2.99	3.799 (3)	143

Symmetry codes: (i) ; (ii) .