(E)-Ethyl 2-anilino-5-[3-(dimethyl-amino)-acrylo-yl]-4-phenyl-thio-phene-3-carboxyl-ate.

In the title compound, C24H24N2O3S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thio-phene ring. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related mol-ecules are linked into dimers by two pairs of C-H⋯O inter-actions.

Related literature

For background to biological activity of thio­phene derivatives see: Mishra et al. (2011 ▶). For the synthesis of different thio­phene derivatives, see: Mabkhot et al. (2011 ▶); Mabkhot, Barakat & Alshahrani (2012 ▶); Mabkhot, Barakat, Al-Majid, Alamary & Al-Nahary (2012 ▶); Mabkhot, Barakat, Al-Majid & Alshahrani (2012 ▶). For related structures, see: Cao et al. (2003 ▶).

Experimental

Crystal data

C24H24N2O3S

M = 420.51

Triclinic,

a = 6.5776 (9) Å

b = 10.7119 (14) Å

c = 16.516 (2) Å

α = 78.459 (3)°

β = 79.743 (3)°

γ = 80.765 (3)°

V = 1112.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 273 K

0.28 × 0.27 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.953, T max = 0.970

12618 measured reflections

4123 independent reflections

3373 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.142

S = 1.05

4123 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003231/rz5041sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003231/rz5041Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003231/rz5041Isup3.cml

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

C24H24N2O3S	Z = 2
Mr = 420.51	F(000) = 444
Triclinic, P1	Dx = 1.255 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5776 (9) Å	Cell parameters from 4320 reflections
b = 10.7119 (14) Å	θ = 1.3–25.5°
c = 16.516 (2) Å	µ = 0.17 mm−1
α = 78.459 (3)°	T = 273 K
β = 79.743 (3)°	Block, yellow
γ = 80.765 (3)°	0.28 × 0.27 × 0.18 mm
V = 1112.5 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	4123 independent reflections
Radiation source: fine-focus sealed tube	3373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 25.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.953, Tmax = 0.970	k = −12→12
12618 measured reflections	l = −19→19

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0761P)2 + 0.2541P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4123 reflections	Δρmax = 0.27 e Å−3
272 parameters	Δρmin = −0.20 e Å−3
0 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: 0.004 (2)

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
S1	0.88423 (8)	0.46635 (5)	0.24436 (3)	0.0586 (2)
O1	0.9061 (3)	0.04813 (14)	0.16466 (10)	0.0714 (4)
O2	1.1246 (3)	0.16911 (16)	0.07700 (11)	0.0837 (5)
O3	0.5995 (3)	0.49861 (18)	0.38688 (12)	0.0932 (6)
N1	1.1535 (3)	0.40198 (17)	0.11137 (11)	0.0613 (5)
H1A	1.1971	0.3505	0.0763	0.074*
N2	0.0937 (3)	0.31677 (18)	0.51004 (11)	0.0648 (5)
C1	1.2694 (3)	0.5907 (2)	0.01997 (14)	0.0666 (6)
H1B	1.2136	0.5698	−0.0228	0.080*
C2	1.3713 (4)	0.6972 (2)	0.00528 (18)	0.0797 (7)
H2B	1.3839	0.7481	−0.0476	0.096*
C3	1.4536 (4)	0.7293 (2)	0.0667 (2)	0.0851 (8)
H3A	1.5233	0.8012	0.0558	0.102*
C4	1.4336 (4)	0.6544 (3)	0.14570 (19)	0.0851 (8)
H4A	1.4881	0.6767	0.1883	0.102*
C5	1.3326 (3)	0.5465 (2)	0.16131 (16)	0.0712 (6)
H5A	1.3205	0.4955	0.2142	0.085*
C6	1.2499 (3)	0.51465 (19)	0.09836 (14)	0.0572 (5)
C7	0.9978 (3)	0.36762 (18)	0.17430 (12)	0.0511 (5)
C8	0.9084 (3)	0.25406 (17)	0.18880 (11)	0.0488 (4)
C9	0.7401 (3)	0.25055 (17)	0.25779 (11)	0.0464 (4)
C10	0.6210 (3)	0.13903 (17)	0.28969 (11)	0.0477 (4)
C11	0.4610 (3)	0.1211 (2)	0.25139 (14)	0.0670 (6)
H11A	0.4247	0.1799	0.2050	0.080*
C12	0.3543 (4)	0.0164 (3)	0.28151 (19)	0.0899 (8)
H12A	0.2458	0.0051	0.2556	0.108*
C13	0.4077 (5)	−0.0709 (3)	0.34945 (19)	0.0919 (9)
H13A	0.3382	−0.1427	0.3688	0.110*
C14	0.5630 (5)	−0.0524 (2)	0.38873 (17)	0.0837 (8)
H14A	0.5969	−0.1105	0.4358	0.100*
C15	0.6697 (4)	0.0519 (2)	0.35904 (14)	0.0652 (6)
H15A	0.7758	0.0637	0.3861	0.078*
C16	0.7077 (3)	0.35877 (18)	0.29284 (12)	0.0510 (5)
C17	0.5610 (3)	0.4031 (2)	0.36344 (13)	0.0592 (5)
C18	0.3834 (3)	0.33914 (19)	0.39894 (13)	0.0560 (5)
H18A	0.3461	0.2800	0.3718	0.067*
C19	0.2683 (3)	0.3641 (2)	0.47208 (13)	0.0578 (5)
H19A	0.3165	0.4201	0.4984	0.069*
C20	0.0008 (4)	0.2328 (3)	0.47236 (17)	0.0910 (9)
H20A	0.0754	0.2277	0.4173	0.136*
H20B	−0.1422	0.2665	0.4687	0.136*
H20C	0.0078	0.1486	0.5061	0.136*
C21	−0.0001 (4)	0.3365 (3)	0.59369 (16)	0.0827 (7)
H21A	0.0754	0.3926	0.6120	0.124*
H21B	0.0049	0.2554	0.6311	0.124*
H21C	−0.1424	0.3745	0.5933	0.124*
C22	0.9907 (3)	0.15623 (19)	0.13755 (13)	0.0578 (5)
C23	0.9697 (5)	−0.0552 (2)	0.11770 (18)	0.0968 (9)
H23A	0.9220	−0.0306	0.0637	0.116*
H23B	1.1205	−0.0732	0.1083	0.116*
C24	0.8828 (6)	−0.1672 (3)	0.1632 (2)	0.1179 (12)
H24A	0.9261	−0.2363	0.1324	0.177*
H24B	0.7335	−0.1494	0.1713	0.177*
H24C	0.9302	−0.1910	0.2166	0.177*

	U11	U22	U33	U12	U13	U23
S1	0.0597 (3)	0.0517 (3)	0.0638 (3)	−0.0230 (2)	0.0070 (2)	−0.0104 (2)
O1	0.0851 (11)	0.0547 (8)	0.0723 (10)	−0.0266 (8)	0.0191 (8)	−0.0197 (7)
O2	0.0937 (12)	0.0687 (10)	0.0789 (11)	−0.0259 (9)	0.0347 (9)	−0.0200 (8)
O3	0.1033 (13)	0.0889 (12)	0.0949 (13)	−0.0538 (11)	0.0363 (10)	−0.0462 (10)
N1	0.0593 (10)	0.0572 (10)	0.0626 (10)	−0.0223 (8)	0.0135 (8)	−0.0077 (8)
N2	0.0615 (10)	0.0710 (11)	0.0586 (10)	−0.0229 (9)	0.0085 (8)	−0.0076 (9)
C1	0.0562 (12)	0.0691 (14)	0.0638 (13)	−0.0128 (10)	0.0044 (10)	0.0052 (11)
C2	0.0621 (14)	0.0681 (15)	0.0893 (18)	−0.0143 (12)	0.0089 (13)	0.0193 (13)
C3	0.0613 (14)	0.0622 (14)	0.121 (2)	−0.0241 (11)	0.0048 (15)	0.0067 (15)
C4	0.0691 (15)	0.0835 (17)	0.106 (2)	−0.0331 (13)	−0.0149 (14)	−0.0050 (15)
C5	0.0605 (13)	0.0720 (14)	0.0771 (15)	−0.0246 (11)	−0.0114 (11)	0.0097 (12)
C6	0.0418 (10)	0.0529 (11)	0.0688 (13)	−0.0110 (8)	0.0034 (9)	0.0015 (9)
C7	0.0478 (10)	0.0496 (10)	0.0522 (10)	−0.0124 (8)	−0.0020 (8)	−0.0007 (8)
C8	0.0486 (10)	0.0471 (10)	0.0484 (10)	−0.0126 (8)	−0.0014 (8)	−0.0030 (8)
C9	0.0460 (10)	0.0475 (10)	0.0444 (9)	−0.0119 (8)	−0.0062 (8)	−0.0009 (8)
C10	0.0478 (10)	0.0465 (10)	0.0466 (10)	−0.0121 (8)	−0.0008 (8)	−0.0041 (8)
C11	0.0658 (13)	0.0723 (14)	0.0640 (13)	−0.0282 (11)	−0.0150 (11)	0.0052 (11)
C12	0.0818 (17)	0.099 (2)	0.0988 (19)	−0.0515 (15)	−0.0179 (15)	−0.0043 (16)
C13	0.097 (2)	0.0732 (16)	0.103 (2)	−0.0499 (15)	0.0031 (17)	0.0069 (15)
C14	0.101 (2)	0.0623 (14)	0.0775 (16)	−0.0230 (14)	−0.0109 (15)	0.0192 (12)
C15	0.0724 (14)	0.0579 (12)	0.0632 (13)	−0.0174 (10)	−0.0158 (11)	0.0062 (10)
C16	0.0487 (10)	0.0520 (11)	0.0513 (10)	−0.0174 (8)	−0.0003 (8)	−0.0048 (8)
C17	0.0621 (12)	0.0575 (12)	0.0577 (12)	−0.0190 (10)	0.0036 (10)	−0.0117 (9)
C18	0.0569 (12)	0.0549 (11)	0.0556 (11)	−0.0150 (9)	0.0013 (9)	−0.0106 (9)
C19	0.0581 (12)	0.0532 (11)	0.0594 (12)	−0.0149 (9)	0.0022 (9)	−0.0071 (9)
C20	0.0783 (17)	0.130 (2)	0.0743 (16)	−0.0554 (17)	−0.0024 (13)	−0.0165 (16)
C21	0.0838 (17)	0.0813 (16)	0.0765 (16)	−0.0251 (13)	0.0255 (13)	−0.0201 (13)
C22	0.0592 (12)	0.0525 (11)	0.0578 (12)	−0.0138 (9)	0.0019 (10)	−0.0049 (9)
C23	0.135 (3)	0.0640 (15)	0.0864 (18)	−0.0254 (16)	0.0287 (17)	−0.0319 (13)
C24	0.144 (3)	0.0774 (19)	0.135 (3)	−0.0471 (19)	0.028 (2)	−0.0445 (19)

S1—C7	1.716 (2)	C10—C15	1.376 (3)
S1—C16	1.7454 (18)	C10—C11	1.376 (3)
O1—C22	1.327 (2)	C11—C12	1.380 (3)
O1—C23	1.443 (3)	C11—H11A	0.9300
O2—C22	1.211 (2)	C12—C13	1.368 (4)
O3—C17	1.240 (2)	C12—H12A	0.9300
N1—C7	1.361 (2)	C13—C14	1.362 (4)
N1—C6	1.414 (3)	C13—H13A	0.9300
N1—H1A	0.8600	C14—C15	1.375 (3)
N2—C19	1.332 (3)	C14—H14A	0.9300
N2—C20	1.451 (3)	C15—H15A	0.9300
N2—C21	1.451 (3)	C16—C17	1.480 (3)
C1—C2	1.374 (3)	C17—C18	1.425 (3)
C1—C6	1.381 (3)	C18—C19	1.357 (3)
C1—H1B	0.9300	C18—H18A	0.9300
C2—C3	1.354 (4)	C19—H19A	0.9300
C2—H2B	0.9300	C20—H20A	0.9600
C3—C4	1.385 (4)	C20—H20B	0.9600
C3—H3A	0.9300	C20—H20C	0.9600
C4—C5	1.382 (3)	C21—H21A	0.9600
C4—H4A	0.9300	C21—H21B	0.9600
C5—C6	1.377 (3)	C21—H21C	0.9600
C5—H5A	0.9300	C23—C24	1.426 (4)
C7—C8	1.395 (3)	C23—H23A	0.9700
C8—C9	1.440 (2)	C23—H23B	0.9700
C8—C22	1.455 (3)	C24—H24A	0.9600
C9—C16	1.367 (3)	C24—H24B	0.9600
C9—C10	1.490 (2)	C24—H24C	0.9600
C7—S1—C16	91.40 (9)	C12—C13—H13A	120.1
C22—O1—C23	118.51 (17)	C13—C14—C15	120.2 (2)
C7—N1—C6	125.94 (18)	C13—C14—H14A	119.9
C7—N1—H1A	117.0	C15—C14—H14A	119.9
C6—N1—H1A	117.0	C14—C15—C10	120.6 (2)
C19—N2—C20	120.91 (19)	C14—C15—H15A	119.7
C19—N2—C21	121.6 (2)	C10—C15—H15A	119.7
C20—N2—C21	117.18 (19)	C9—C16—C17	134.44 (18)
C2—C1—C6	119.8 (2)	C9—C16—S1	112.14 (14)
C2—C1—H1B	120.1	C17—C16—S1	113.40 (14)
C6—C1—H1B	120.1	O3—C17—C18	123.6 (2)
C3—C2—C1	121.0 (2)	O3—C17—C16	116.37 (18)
C3—C2—H2B	119.5	C18—C17—C16	120.04 (18)
C1—C2—H2B	119.5	C19—C18—C17	120.38 (19)
C2—C3—C4	119.7 (2)	C19—C18—H18A	119.8
C2—C3—H3A	120.2	C17—C18—H18A	119.8
C4—C3—H3A	120.2	N2—C19—C18	126.8 (2)
C5—C4—C3	120.0 (3)	N2—C19—H19A	116.6
C5—C4—H4A	120.0	C18—C19—H19A	116.6
C3—C4—H4A	120.0	N2—C20—H20A	109.5
C6—C5—C4	119.8 (2)	N2—C20—H20B	109.5
C6—C5—H5A	120.1	H20A—C20—H20B	109.5
C4—C5—H5A	120.1	N2—C20—H20C	109.5
C5—C6—C1	119.7 (2)	H20A—C20—H20C	109.5
C5—C6—N1	121.13 (19)	H20B—C20—H20C	109.5
C1—C6—N1	119.1 (2)	N2—C21—H21A	109.5
N1—C7—C8	125.77 (18)	N2—C21—H21B	109.5
N1—C7—S1	121.90 (15)	H21A—C21—H21B	109.5
C8—C7—S1	112.31 (14)	N2—C21—H21C	109.5
C7—C8—C9	111.73 (17)	H21A—C21—H21C	109.5
C7—C8—C22	120.01 (17)	H21B—C21—H21C	109.5
C9—C8—C22	128.25 (17)	O2—C22—O1	122.38 (19)
C16—C9—C8	112.39 (16)	O2—C22—C8	124.57 (19)
C16—C9—C10	123.85 (17)	O1—C22—C8	113.04 (17)
C8—C9—C10	123.71 (16)	C24—C23—O1	109.3 (2)
C15—C10—C11	118.77 (18)	C24—C23—H23A	109.8
C15—C10—C9	119.88 (17)	O1—C23—H23A	109.8
C11—C10—C9	121.34 (17)	C24—C23—H23B	109.8
C10—C11—C12	120.3 (2)	O1—C23—H23B	109.8
C10—C11—H11A	119.8	H23A—C23—H23B	108.3
C12—C11—H11A	119.8	C23—C24—H24A	109.5
C13—C12—C11	120.2 (2)	C23—C24—H24B	109.5
C13—C12—H12A	119.9	H24A—C24—H24B	109.5
C11—C12—H12A	119.9	C23—C24—H24C	109.5
C14—C13—C12	119.8 (2)	H24A—C24—H24C	109.5
C14—C13—H13A	120.1	H24B—C24—H24C	109.5
C6—C1—C2—C3	0.0 (4)	C10—C11—C12—C13	−0.4 (4)
C1—C2—C3—C4	−0.6 (4)	C11—C12—C13—C14	1.8 (5)
C2—C3—C4—C5	1.0 (4)	C12—C13—C14—C15	−1.7 (5)
C3—C4—C5—C6	−0.8 (4)	C13—C14—C15—C10	0.2 (4)
C4—C5—C6—C1	0.2 (3)	C11—C10—C15—C14	1.1 (3)
C4—C5—C6—N1	177.3 (2)	C9—C10—C15—C14	−179.2 (2)
C2—C1—C6—C5	0.2 (3)	C8—C9—C16—C17	−179.4 (2)
C2—C1—C6—N1	−177.0 (2)	C10—C9—C16—C17	−1.9 (4)
C7—N1—C6—C5	52.8 (3)	C8—C9—C16—S1	−1.2 (2)
C7—N1—C6—C1	−130.1 (2)	C10—C9—C16—S1	176.24 (14)
C6—N1—C7—C8	−177.4 (2)	C7—S1—C16—C9	1.72 (16)
C6—N1—C7—S1	4.4 (3)	C7—S1—C16—C17	−179.70 (16)
C16—S1—C7—N1	176.63 (17)	C9—C16—C17—O3	168.0 (2)
C16—S1—C7—C8	−1.78 (16)	S1—C16—C17—O3	−10.2 (3)
N1—C7—C8—C9	−176.91 (18)	C9—C16—C17—C18	−13.9 (4)
S1—C7—C8—C9	1.4 (2)	S1—C16—C17—C18	167.92 (16)
N1—C7—C8—C22	4.2 (3)	O3—C17—C18—C19	−13.4 (4)
S1—C7—C8—C22	−177.48 (15)	C16—C17—C18—C19	168.64 (19)
C7—C8—C9—C16	−0.1 (2)	C20—N2—C19—C18	−2.6 (4)
C22—C8—C9—C16	178.68 (19)	C21—N2—C19—C18	171.4 (2)
C7—C8—C9—C10	−177.58 (17)	C17—C18—C19—N2	176.3 (2)
C22—C8—C9—C10	1.2 (3)	C23—O1—C22—O2	−3.0 (4)
C16—C9—C10—C15	−78.4 (3)	C23—O1—C22—C8	178.1 (2)
C8—C9—C10—C15	98.8 (2)	C7—C8—C22—O2	−6.2 (3)
C16—C9—C10—C11	101.3 (2)	C9—C8—C22—O2	175.1 (2)
C8—C9—C10—C11	−81.5 (3)	C7—C8—C22—O1	172.74 (18)
C15—C10—C11—C12	−1.0 (4)	C9—C8—C22—O1	−6.0 (3)
C9—C10—C11—C12	179.3 (2)	C22—O1—C23—C24	172.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.07	2.709 (3)	130
C19—H19A···O3i	0.93	2.42	3.294 (3)	157
C21—H21A···O3i	0.96	2.60	3.491 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.07	2.709 (3)	130
C19—H19A⋯O3i	0.93	2.42	3.294 (3)	157
C21—H21A⋯O3i	0.96	2.60	3.491 (4)	155

Symmetry code: (i) .