Diethyl 2-{[3-(2-meth-oxy-benz-yl)thio-phen-2-yl]methyl-idene}malonate.

In the title compound, C(20)H(22)O(5)S, the dihedral angle between the mean planes through the thio-phene and benzene rings is 75.2 (1)°. The meth-oxy group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.019 (2) Å for the O atom. The malonate group assumes an extended conformation.

Related literature

For the biological activities of thio­phene derivatives, see: Bonini et al. (2005 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For a similar thio­phene structure, see: Dufresne & Skene (2010 ▶).

Experimental

Crystal data

C20H22O5S

M = 374.44

Orthorhombic,

a = 8.1680 (2) Å

b = 16.4046 (4) Å

c = 28.8651 (7) Å

V = 3867.72 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.19 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 = 0.953, T max = 0.964

35690 measured reflections

3695 independent reflections

2687 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.145

S = 1.02

3695 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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/S1600536811022525/nk2101sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022525/nk2101Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022525/nk2101Isup3.cml

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

C20H22O5S	F(000) = 1584
Mr = 374.44	Dx = 1.286 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3696 reflections
a = 8.1680 (2) Å	θ = 1.4–25.8°
b = 16.4046 (4) Å	µ = 0.19 mm−1
c = 28.8651 (7) Å	T = 293 K
V = 3867.72 (16) Å3	Block, white
Z = 8	0.25 × 0.22 × 0.19 mm

Bruker APEXII CCD area detector diffractometer	3695 independent reflections
Radiation source: fine-focus sealed tube	2687 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω and φ scans	θmax = 25.8°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.953, Tmax = 0.964	k = −20→19
35690 measured reflections	l = −35→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0896P)2 + 0.4403P] where P = (Fo2 + 2Fc2)/3
3695 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.2480 (3)	0.84683 (13)	0.40960 (7)	0.0502 (5)
H1	0.2853	0.7955	0.4182	0.060*
C2	0.0917 (3)	0.87086 (14)	0.41448 (8)	0.0577 (6)
H2	0.0097	0.8382	0.4270	0.069*
C3	0.2653 (2)	0.97752 (12)	0.37999 (6)	0.0406 (5)
C4	0.3501 (2)	0.90728 (11)	0.39004 (6)	0.0391 (4)
C5	0.5308 (2)	0.89232 (12)	0.38274 (6)	0.0416 (5)
H5A	0.5455	0.8420	0.3656	0.050*
H5B	0.5764	0.9363	0.3644	0.050*
C6	0.6220 (2)	0.88675 (12)	0.42814 (6)	0.0392 (4)
C7	0.6554 (3)	0.81224 (12)	0.44834 (7)	0.0499 (5)
H7	0.6246	0.7646	0.4332	0.060*
C8	0.7338 (3)	0.80722 (15)	0.49063 (8)	0.0605 (6)
H8	0.7551	0.7566	0.5039	0.073*
C9	0.7800 (3)	0.87723 (15)	0.51296 (7)	0.0600 (6)
H9	0.8333	0.8739	0.5414	0.072*
C10	0.7487 (3)	0.95238 (14)	0.49386 (7)	0.0541 (6)
H10	0.7799	0.9996	0.5094	0.065*
C11	0.6703 (2)	0.95747 (11)	0.45135 (7)	0.0415 (5)
C12	0.6731 (3)	1.10362 (14)	0.45138 (9)	0.0702 (7)
H12A	0.6190	1.1058	0.4809	0.105*
H12B	0.6364	1.1481	0.4325	0.105*
H12C	0.7893	1.1076	0.4559	0.105*
C13	0.3340 (2)	1.05129 (11)	0.36133 (6)	0.0410 (5)
H13	0.4477	1.0519	0.3598	0.049*
C14	0.2619 (2)	1.11897 (12)	0.34583 (6)	0.0418 (5)
C15	0.0810 (2)	1.13214 (12)	0.34553 (7)	0.0467 (5)
C16	−0.1688 (3)	1.09125 (18)	0.31161 (12)	0.0825 (9)
H16A	−0.2077	1.1441	0.3013	0.099*
H16B	−0.2117	1.0811	0.3424	0.099*
C17	−0.2233 (4)	1.0273 (3)	0.27952 (11)	0.1122 (13)
H17A	−0.1722	1.0351	0.2499	0.168*
H17B	−0.3401	1.0300	0.2761	0.168*
H17C	−0.1933	0.9748	0.2916	0.168*
C18	0.3658 (3)	1.18679 (13)	0.32912 (8)	0.0541 (6)
C19	0.3623 (4)	1.31693 (16)	0.29168 (9)	0.0758 (8)
H19A	0.2947	1.3649	0.2963	0.091*
H19B	0.4635	1.3244	0.3088	0.091*
C20	0.3981 (4)	1.3071 (2)	0.24258 (10)	0.0962 (10)
H20A	0.4699	1.2614	0.2383	0.144*
H20B	0.4500	1.3556	0.2311	0.144*
H20C	0.2980	1.2980	0.2259	0.144*
O1	0.63527 (19)	1.02826 (8)	0.42901 (5)	0.0542 (4)
O2	0.0111 (2)	1.17398 (10)	0.37271 (7)	0.0752 (5)
O3	0.00937 (18)	1.08978 (10)	0.31226 (5)	0.0587 (4)
O4	0.5109 (2)	1.18958 (11)	0.33296 (8)	0.0910 (7)
O5	0.2766 (2)	1.24465 (9)	0.30883 (5)	0.0639 (5)
S1	0.06061 (7)	0.96745 (4)	0.39524 (2)	0.0526 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0581 (14)	0.0429 (11)	0.0496 (11)	−0.0054 (10)	−0.0043 (10)	0.0073 (9)
C2	0.0579 (15)	0.0586 (14)	0.0565 (13)	−0.0150 (12)	0.0021 (11)	0.0091 (11)
C3	0.0398 (11)	0.0421 (11)	0.0399 (10)	0.0006 (8)	−0.0028 (8)	−0.0007 (8)
C4	0.0450 (12)	0.0387 (10)	0.0338 (9)	−0.0009 (8)	−0.0038 (8)	−0.0015 (8)
C5	0.0489 (12)	0.0380 (10)	0.0378 (10)	0.0053 (9)	−0.0007 (9)	−0.0010 (8)
C6	0.0382 (10)	0.0396 (10)	0.0397 (10)	0.0030 (8)	0.0012 (8)	−0.0015 (8)
C7	0.0595 (14)	0.0385 (11)	0.0516 (12)	0.0054 (10)	−0.0067 (10)	−0.0025 (9)
C8	0.0754 (16)	0.0534 (14)	0.0526 (13)	0.0114 (12)	−0.0090 (11)	0.0089 (10)
C9	0.0710 (16)	0.0669 (16)	0.0422 (12)	0.0082 (13)	−0.0118 (11)	0.0015 (11)
C10	0.0600 (14)	0.0544 (14)	0.0478 (12)	−0.0047 (10)	−0.0056 (11)	−0.0106 (10)
C11	0.0420 (11)	0.0369 (10)	0.0457 (11)	0.0004 (8)	0.0015 (9)	−0.0011 (8)
C12	0.0827 (18)	0.0391 (12)	0.0889 (18)	−0.0098 (12)	−0.0012 (14)	−0.0097 (12)
C13	0.0364 (10)	0.0416 (11)	0.0450 (11)	0.0006 (8)	0.0001 (8)	−0.0002 (8)
C14	0.0389 (11)	0.0385 (10)	0.0480 (11)	0.0017 (8)	0.0007 (9)	−0.0007 (8)
C15	0.0447 (12)	0.0361 (10)	0.0592 (13)	0.0028 (9)	0.0043 (10)	0.0044 (10)
C16	0.0380 (13)	0.088 (2)	0.121 (2)	0.0024 (13)	−0.0115 (14)	0.0139 (18)
C17	0.070 (2)	0.178 (4)	0.088 (2)	−0.035 (2)	−0.0234 (17)	0.002 (2)
C18	0.0474 (14)	0.0444 (12)	0.0706 (14)	0.0025 (10)	0.0056 (11)	0.0067 (11)
C19	0.096 (2)	0.0568 (15)	0.0747 (17)	−0.0089 (14)	0.0089 (15)	0.0113 (13)
C20	0.111 (3)	0.101 (2)	0.0764 (19)	−0.0050 (19)	0.0193 (17)	0.0097 (17)
O1	0.0689 (10)	0.0344 (7)	0.0593 (9)	−0.0046 (7)	−0.0092 (7)	−0.0008 (6)
O2	0.0597 (10)	0.0637 (11)	0.1023 (13)	0.0107 (9)	0.0193 (10)	−0.0254 (10)
O3	0.0378 (8)	0.0702 (10)	0.0681 (10)	0.0033 (7)	−0.0059 (7)	−0.0051 (8)
O4	0.0428 (10)	0.0703 (12)	0.160 (2)	−0.0049 (9)	0.0016 (11)	0.0353 (12)
O5	0.0642 (10)	0.0492 (9)	0.0782 (11)	−0.0018 (8)	−0.0022 (8)	0.0227 (8)
S1	0.0422 (3)	0.0553 (4)	0.0603 (4)	−0.0012 (2)	0.0033 (2)	0.0067 (3)

C1—C2	1.344 (3)	C12—H12B	0.9600
C1—C4	1.413 (3)	C12—H12C	0.9600
C1—H1	0.9300	C13—C14	1.334 (3)
C2—S1	1.698 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C18	1.480 (3)
C3—C4	1.375 (3)	C14—C15	1.493 (3)
C3—C13	1.439 (3)	C15—O2	1.189 (2)
C3—S1	1.737 (2)	C15—O3	1.322 (3)
C4—C5	1.511 (3)	C16—O3	1.456 (3)
C5—C6	1.510 (3)	C16—C17	1.469 (4)
C5—H5A	0.9700	C16—H16A	0.9700
C5—H5B	0.9700	C16—H16B	0.9700
C6—C7	1.381 (3)	C17—H17A	0.9600
C6—C11	1.396 (3)	C17—H17B	0.9600
C7—C8	1.381 (3)	C17—H17C	0.9600
C7—H7	0.9300	C18—O4	1.192 (3)
C8—C9	1.370 (3)	C18—O5	1.332 (3)
C8—H8	0.9300	C19—C20	1.456 (4)
C9—C10	1.375 (3)	C19—O5	1.463 (3)
C9—H9	0.9300	C19—H19A	0.9700
C10—C11	1.387 (3)	C19—H19B	0.9700
C10—H10	0.9300	C20—H20A	0.9600
C11—O1	1.359 (2)	C20—H20B	0.9600
C12—O1	1.429 (3)	C20—H20C	0.9600
C12—H12A	0.9600
C2—C1—C4	113.4 (2)	H12B—C12—H12C	109.5
C2—C1—H1	123.3	C14—C13—C3	130.83 (19)
C4—C1—H1	123.3	C14—C13—H13	114.6
C1—C2—S1	112.43 (17)	C3—C13—H13	114.6
C1—C2—H2	123.8	C13—C14—C18	118.84 (18)
S1—C2—H2	123.8	C13—C14—C15	123.97 (18)
C4—C3—C13	125.96 (18)	C18—C14—C15	117.16 (17)
C4—C3—S1	110.60 (15)	O2—C15—O3	124.75 (19)
C13—C3—S1	123.39 (15)	O2—C15—C14	123.7 (2)
C3—C4—C1	112.01 (18)	O3—C15—C14	111.48 (17)
C3—C4—C5	126.77 (17)	O3—C16—C17	107.4 (2)
C1—C4—C5	121.21 (18)	O3—C16—H16A	110.2
C6—C5—C4	111.75 (15)	C17—C16—H16A	110.2
C6—C5—H5A	109.3	O3—C16—H16B	110.2
C4—C5—H5A	109.3	C17—C16—H16B	110.2
C6—C5—H5B	109.3	H16A—C16—H16B	108.5
C4—C5—H5B	109.3	C16—C17—H17A	109.5
H5A—C5—H5B	107.9	C16—C17—H17B	109.5
C7—C6—C11	118.48 (17)	H17A—C17—H17B	109.5
C7—C6—C5	121.15 (17)	C16—C17—H17C	109.5
C11—C6—C5	120.34 (17)	H17A—C17—H17C	109.5
C6—C7—C8	121.2 (2)	H17B—C17—H17C	109.5
C6—C7—H7	119.4	O4—C18—O5	123.9 (2)
C8—C7—H7	119.4	O4—C18—C14	124.7 (2)
C9—C8—C7	119.6 (2)	O5—C18—C14	111.45 (18)
C9—C8—H8	120.2	C20—C19—O5	109.6 (2)
C7—C8—H8	120.2	C20—C19—H19A	109.7
C8—C9—C10	120.78 (19)	O5—C19—H19A	109.7
C8—C9—H9	119.6	C20—C19—H19B	109.7
C10—C9—H9	119.6	O5—C19—H19B	109.7
C9—C10—C11	119.7 (2)	H19A—C19—H19B	108.2
C9—C10—H10	120.2	C19—C20—H20A	109.5
C11—C10—H10	120.2	C19—C20—H20B	109.5
O1—C11—C10	124.65 (18)	H20A—C20—H20B	109.5
O1—C11—C6	115.03 (17)	C19—C20—H20C	109.5
C10—C11—C6	120.32 (18)	H20A—C20—H20C	109.5
O1—C12—H12A	109.5	H20B—C20—H20C	109.5
O1—C12—H12B	109.5	C11—O1—C12	118.66 (17)
H12A—C12—H12B	109.5	C15—O3—C16	116.32 (19)
O1—C12—H12C	109.5	C18—O5—C19	117.7 (2)
H12A—C12—H12C	109.5	C2—S1—C3	91.58 (10)
C4—C1—C2—S1	0.5 (2)	S1—C3—C13—C14	−10.9 (3)
C13—C3—C4—C1	177.77 (18)	C3—C13—C14—C18	178.9 (2)
S1—C3—C4—C1	0.3 (2)	C3—C13—C14—C15	0.9 (3)
C13—C3—C4—C5	−1.4 (3)	C13—C14—C15—O2	103.5 (3)
S1—C3—C4—C5	−178.86 (14)	C18—C14—C15—O2	−74.5 (3)
C2—C1—C4—C3	−0.5 (3)	C13—C14—C15—O3	−74.7 (2)
C2—C1—C4—C5	178.72 (18)	C18—C14—C15—O3	107.2 (2)
C3—C4—C5—C6	110.5 (2)	C13—C14—C18—O4	−8.6 (3)
C1—C4—C5—C6	−68.6 (2)	C15—C14—C18—O4	169.6 (2)
C4—C5—C6—C7	96.2 (2)	C13—C14—C18—O5	171.06 (18)
C4—C5—C6—C11	−81.9 (2)	C15—C14—C18—O5	−10.8 (3)
C11—C6—C7—C8	0.4 (3)	C10—C11—O1—C12	−3.5 (3)
C5—C6—C7—C8	−177.7 (2)	C6—C11—O1—C12	176.92 (18)
C6—C7—C8—C9	−0.2 (4)	O2—C15—O3—C16	−4.3 (3)
C7—C8—C9—C10	0.3 (4)	C14—C15—O3—C16	173.90 (19)
C8—C9—C10—C11	−0.4 (4)	C17—C16—O3—C15	−167.5 (2)
C9—C10—C11—O1	−179.0 (2)	O4—C18—O5—C19	−2.1 (4)
C9—C10—C11—C6	0.5 (3)	C14—C18—O5—C19	178.30 (19)
C7—C6—C11—O1	179.11 (18)	C20—C19—O5—C18	95.8 (3)
C5—C6—C11—O1	−2.8 (3)	C1—C2—S1—C3	−0.25 (18)
C7—C6—C11—C10	−0.5 (3)	C4—C3—S1—C2	−0.03 (16)
C5—C6—C11—C10	177.62 (19)	C13—C3—S1—C2	−177.60 (17)
C4—C3—C13—C14	171.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.93	2.55	3.429 (3)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.93	2.55	3.429 (3)	159

Symmetry code: (i) .