(E)-Ethyl 2-anilino-5-[3-(dimethyl­amino)­acrylo­yl]-4-phenyl­thio­phene-3-carboxyl­ate

Mabkhot, Y.N.; Barakat, A.; Alatibi, F.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S1600536813003231

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o351

doi:10.1107/S1600536813003231

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(E)-Ethyl 2-anilino-5-[3-(dimethylamino)acryloyl]-4-phenylthiophene-3-carboxylate

Yahia Nasser Mabkhot,^a ^* Assem Barakat,^a,^b Fatima Alatibi,^a M. Iqbal Choudhary ^c,^a and Sammer Yousuf ^c ^*

^aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia, 21321 Alexandria, Egypt, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: yahia@ksu.edu.sa, dr.sammer.yousuf@gmail.com

(Received 28 January 2013; accepted 31 January 2013; online 6 February 2013)

In the title compound, C₂₄H₂₄N₂O₃S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thiophene ring. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related molecules are linked into dimers by two pairs of C—H⋯O interactions.

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_r = 420.51
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.142
S = 1.05
4123 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003231/rz5041sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813003231/rz5041Isup3.cml

checkCIF report

Comment top

Thiophene moeities containing hetereocyclic compounds are well known for their wide range of biological activities such as antidiabetic, antiinflammatory, antibacterial, antidepressent and antiellergic (Mishra et al., 2011). Mabkhot and co-workers have been extensively involved in the synthesis of biologically valuable thiophene derivatives (Mabkhot et al., 2011; Mabkhot, Barakat & Alshahrani, 2012; Mabkhot, Barakat, Al-Majid Alamary & Al-Nahary, 2012; Mabkhot, Barakat, Al-Majid & Alshahrani, 2012). The title compound is an enaminone derivative of a substituted thiophene nucleus, and was synthesized in order to create a library for the evaluation of different biological activities.

The structure of the title compound is composed of a central thiophene unit (S1/C7–C9/C16) with an aminophenyl (N1/C1–C6), an ethyl acyl (O1–O2/C22—C24), a phenyl (C10–C15) and an enaminone (O3/N2/C17–C21) susbtituent attached to C7, C8, C9 and C16, respectively. The thiophene and phenyl rings form dihedral angles of 55.65 (11), 79.60 (11) and 24.67 (12)° between S1/C7–C9/C16 and C1–C6, S1/C7–C9/C16 and C10–C15) and C1–C6 and C10–C15, respectively. The C18–C19 (1.357 (3) Å) olefinic bond of the enaminone side chain has an E configuration. The shorter C—C bond length of C17–C18 (1.423 (3) Å), as compared to single bond (1.54 Å), indicates that the olefinic bond is involved in conjugation with a carbonyl functionality (C17–O3, 1.240 (2) Å). The bond lengths and angles were found to be in same range as in other related compounds (Cao et al., 2003). The conformation of the molecule is stabilized by an N1—H1A···O2 intramolecular hydrogen bond to form an S6 graph set ring motif (Fig. 1, Table 1). In the crystal (Fig. 2), centrosymmetrically related molecules are linked via C19—H19A···O3 and C21—H21A···O3 intermolecular hydrogen bonds (symmetry codes as in Table 1) into dimers.

Related literature top

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 top

The title compound was synthesized by following the same procedure as described by Mabkhot et al., 2011). The compound was recrystallized from a 95% ethanol solution to obtain dark yellow crystals (m. p. 440 K) found to be suitable for single-crystal X-ray data collection. All chemicals were purchased from Sigma- Aldrich.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of title compound with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. Crystal packing of the title compound viewed along the a axis. Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.

(E)-Ethyl 2-anilino-5-[3-(dimethylamino)acryloyl]-4-phenylthiophene-3-carboxylate top

Crystal data top

C₂₄H₂₄N₂O₃S	Z = 2
M_r = 420.51	F(000) = 444
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0761P)² + 0.2541P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4123 reflections	Δρ_max = 0.27 e Å⁻³
272 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₄N₂O₃S	γ = 80.765 (3)°
M_r = 420.51	V = 1112.5 (3) Å³
Triclinic, P1	Z = 2
a = 6.5776 (9) Å	Mo Kα radiation
b = 10.7119 (14) Å	µ = 0.17 mm⁻¹
c = 16.516 (2) Å	T = 273 K
α = 78.459 (3)°	0.28 × 0.27 × 0.18 mm
β = 79.743 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4123 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3373 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.970	R_int = 0.021
12618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
4123 reflections	Δρ_min = −0.20 e Å⁻³
272 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₃S
M_r	420.51
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	6.5776 (9), 10.7119 (14), 16.516 (2)
α, β, γ (°)	78.459 (3), 79.743 (3), 80.765 (3)
V (Å³)	1112.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.28 × 0.27 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.953, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	12618, 4123, 3373
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 1.05
No. of reflections	4123
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.8600	2.0700	2.709 (3)	130.00
C19—H19A···O3ⁱ	0.9300	2.4200	3.294 (3)	157.00
C21—H21A···O3ⁱ	0.9600	2.6000	3.491 (4)	155.00

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This project was supported by King Saud University, Deanship of Scientific Research, College of Science Research Center.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, K.-G., Wang, Z.-W., Zhao, X.-Q. & Fang, T. (2003). Chin. J. Org. Chem. 23, 1411–1415. CAS Google Scholar
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Alamary, A. S. & Al-Nahary, T. T. (2012). Int. J. Mol. Sci. 13, 5035–5047. Web of Science CrossRef CAS PubMed Google Scholar
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Al-Othman, Z. A. & Alamary, A. S. (2011). Int. J. Mol. Sci. 12, 7824–7834. Web of Science CAS PubMed Google Scholar
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263–2275. Web of Science CrossRef CAS PubMed Google Scholar
Mabkhot, Y. N., Barakat, A. & Alshahrani, S. (2012). J. Mol. Struct., 1027, 15–19. Web of Science CrossRef CAS Google Scholar
Mishra, R., Tomar, I., Singhal, S. & Jha, K. K. (2011). Pharma Chem. 3, 38–54. CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 3| March 2013| Page o351

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(E)-Ethyl 2-anilino-5-[3-(di­methyl­amino)­acrylo­yl]-4-phenyl­thio­phene-3-carboxyl­ate

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Experimental

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organic compounds

(E)-Ethyl 2-anilino-5-[3-(dimethylamino)acryloyl]-4-phenylthiophene-3-carboxylate