Ethyl 4-acetyl-5-anilino-3-methyl-thio-phene-2-carboxyl-ate.

In the title compound, C16H17NO3S, a thio-phene derivative with amino phenyl, acetyl, methyl and ethyl carboxyl susbtituents attached to a central thio-phene ring, the phenyl and thio-phene rings form a dihedral angle of 36.92 (9) Å. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, which forms an S(6) ring motif.

Related literature

For the biological activity of thio­phene derivatives, see: Mishra et al. (2011 ▶); Mabkhot et al. (2013b ▶). For the synthesis of fused heterocyclic compounds, see: Sommen et al. (2003 ▶). For crystal data for related thio­phene compounds, see: Mabkhot et al. (2013a ▶,b ▶); Buehrdel et al. (2007 ▶).

Experimental

Crystal data

C16H17NO3S

M = 303.37

Triclinic,

a = 7.9443 (6) Å

b = 9.5038 (7) Å

c = 11.8706 (9) Å

α = 66.759 (2)°

β = 89.754 (2)°

γ = 66.785 (2)°

V = 744.60 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 273 K

0.45 × 0.42 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.905, T max = 0.950

10410 measured reflections

3699 independent reflections

2848 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.126

S = 1.05

3699 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.25 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; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301547X/rz5071sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301547X/rz5071Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301547X/rz5071Isup3.cml

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

C16H17NO3S	Z = 2
Mr = 303.37	F(000) = 320
Triclinic, P1	Dx = 1.353 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9443 (6) Å	Cell parameters from 2619 reflections
b = 9.5038 (7) Å	θ = 2.5–25.8°
c = 11.8706 (9) Å	µ = 0.23 mm−1
α = 66.759 (2)°	T = 273 K
β = 89.754 (2)°	Block, yellow
γ = 66.785 (2)°	0.45 × 0.42 × 0.23 mm
V = 744.60 (10) Å3

Bruker SMART APEX CCD area-detector diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	2848 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scan	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.905, Tmax = 0.950	k = −12→12
10410 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.0954P] where P = (Fo2 + 2Fc2)/3
3699 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.25 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
S1	0.48333 (6)	0.26835 (5)	−0.00730 (4)	0.04325 (15)
O1	0.8347 (2)	0.01329 (18)	−0.22852 (13)	0.0685 (4)
O2	0.6413 (2)	−0.06433 (17)	0.34080 (12)	0.0704 (5)
O3	0.41944 (19)	0.19842 (16)	0.23323 (11)	0.0546 (3)
N1	0.5630 (2)	0.2832 (2)	−0.23190 (14)	0.0483 (4)
C2	0.6046 (2)	0.1930 (2)	−0.10687 (15)	0.0404 (4)
C3	0.7453 (2)	0.0270 (2)	−0.04358 (15)	0.0407 (4)
C4	0.7482 (2)	−0.0370 (2)	0.08869 (15)	0.0394 (4)
C5	0.6149 (2)	0.0774 (2)	0.12066 (15)	0.0419 (4)
C6	0.5653 (3)	0.0580 (2)	0.24344 (16)	0.0475 (4)
C7	0.3506 (3)	0.1937 (3)	0.34727 (19)	0.0634 (6)
H7A	0.4503	0.1639	0.4111	0.076*
H7B	0.2996	0.1109	0.3776	0.076*
C8	0.2028 (3)	0.3670 (3)	0.3158 (2)	0.0728 (6)
H8A	0.1526	0.3702	0.3889	0.109*
H8B	0.1054	0.3948	0.2524	0.109*
H8C	0.2553	0.4475	0.2858	0.109*
C9	0.8800 (3)	−0.2083 (2)	0.18489 (17)	0.0539 (5)
H9A	0.8528	−0.2197	0.2661	0.081*
H9B	1.0055	−0.2205	0.1820	0.081*
H9C	0.8659	−0.2944	0.1682	0.081*
C10	0.8559 (2)	−0.0600 (2)	−0.11438 (17)	0.0466 (4)
C11	0.9989 (3)	−0.2421 (3)	−0.0534 (2)	0.0605 (5)
H11A	1.0558	−0.2749	−0.1159	0.091*
H11B	0.9394	−0.3133	−0.0102	0.091*
H11C	1.0925	−0.2538	0.0049	0.091*
C12	0.4166 (2)	0.4428 (2)	−0.30492 (15)	0.0435 (4)
C13	0.3570 (3)	0.5761 (2)	−0.27179 (18)	0.0536 (5)
H13A	0.4097	0.5614	−0.1958	0.064*
C14	0.2190 (3)	0.7316 (2)	−0.3516 (2)	0.0640 (6)
H14A	0.1781	0.8210	−0.3286	0.077*
C15	0.1418 (3)	0.7551 (3)	−0.4643 (2)	0.0665 (6)
H15A	0.0501	0.8603	−0.5181	0.080*
C16	0.2008 (3)	0.6224 (3)	−0.49714 (19)	0.0653 (6)
H16A	0.1484	0.6380	−0.5735	0.078*
C17	0.3366 (3)	0.4667 (2)	−0.41818 (17)	0.0540 (5)
H17A	0.3750	0.3772	−0.4409	0.065*
H1A	0.627 (3)	0.228 (3)	−0.267 (2)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0447 (3)	0.0347 (2)	0.0357 (2)	−0.00843 (18)	0.00177 (18)	−0.00958 (17)
O1	0.0810 (10)	0.0576 (9)	0.0452 (8)	−0.0093 (8)	0.0116 (7)	−0.0217 (7)
O2	0.0924 (11)	0.0462 (8)	0.0366 (7)	−0.0056 (7)	0.0057 (7)	−0.0072 (6)
O3	0.0653 (8)	0.0428 (7)	0.0390 (7)	−0.0107 (6)	0.0109 (6)	−0.0139 (6)
N1	0.0532 (9)	0.0401 (8)	0.0330 (8)	−0.0071 (7)	0.0017 (7)	−0.0105 (6)
C2	0.0419 (9)	0.0394 (9)	0.0344 (8)	−0.0161 (7)	0.0013 (7)	−0.0119 (7)
C3	0.0382 (9)	0.0379 (8)	0.0387 (9)	−0.0121 (7)	0.0011 (7)	−0.0136 (7)
C4	0.0379 (8)	0.0348 (8)	0.0369 (8)	−0.0121 (7)	−0.0019 (7)	−0.0105 (7)
C5	0.0459 (9)	0.0357 (8)	0.0331 (8)	−0.0132 (7)	−0.0013 (7)	−0.0084 (7)
C6	0.0573 (11)	0.0370 (9)	0.0381 (9)	−0.0144 (8)	0.0025 (8)	−0.0121 (7)
C7	0.0785 (15)	0.0569 (12)	0.0454 (11)	−0.0198 (11)	0.0207 (10)	−0.0223 (10)
C8	0.0731 (15)	0.0667 (14)	0.0759 (16)	−0.0192 (12)	0.0235 (13)	−0.0386 (13)
C9	0.0515 (11)	0.0418 (10)	0.0426 (10)	−0.0044 (8)	−0.0029 (8)	−0.0090 (8)
C10	0.0447 (10)	0.0452 (10)	0.0461 (10)	−0.0156 (8)	0.0045 (8)	−0.0194 (8)
C11	0.0581 (12)	0.0510 (11)	0.0601 (13)	−0.0085 (9)	0.0104 (10)	−0.0268 (10)
C12	0.0440 (9)	0.0390 (9)	0.0351 (9)	−0.0153 (7)	0.0041 (7)	−0.0065 (7)
C13	0.0664 (13)	0.0430 (10)	0.0415 (10)	−0.0210 (9)	−0.0020 (9)	−0.0107 (8)
C14	0.0776 (15)	0.0396 (10)	0.0563 (13)	−0.0154 (10)	0.0040 (11)	−0.0126 (9)
C15	0.0637 (13)	0.0466 (11)	0.0528 (12)	−0.0064 (10)	−0.0046 (10)	−0.0034 (9)
C16	0.0684 (14)	0.0613 (13)	0.0417 (11)	−0.0148 (11)	−0.0086 (10)	−0.0112 (10)
C17	0.0619 (12)	0.0493 (10)	0.0368 (10)	−0.0146 (9)	0.0011 (8)	−0.0140 (8)

S1—C2	1.7182 (18)	C8—H8C	0.9600
S1—C5	1.7422 (16)	C9—H9A	0.9600
O1—C10	1.230 (2)	C9—H9B	0.9600
O2—C6	1.202 (2)	C9—H9C	0.9600
O3—C6	1.339 (2)	C10—C11	1.509 (3)
O3—C7	1.449 (2)	C11—H11A	0.9600
N1—C2	1.350 (2)	C11—H11B	0.9600
N1—C12	1.409 (2)	C11—H11C	0.9600
N1—H1A	0.82 (2)	C12—C13	1.379 (3)
C2—C3	1.409 (2)	C12—C17	1.384 (3)
C3—C4	1.439 (2)	C13—C14	1.382 (3)
C3—C10	1.460 (2)	C13—H13A	0.9300
C4—C5	1.365 (2)	C14—C15	1.371 (3)
C4—C9	1.500 (2)	C14—H14A	0.9300
C5—C6	1.468 (2)	C15—C16	1.372 (3)
C7—C8	1.491 (3)	C15—H15A	0.9300
C7—H7A	0.9700	C16—C17	1.374 (3)
C7—H7B	0.9700	C16—H16A	0.9300
C8—H8A	0.9600	C17—H17A	0.9300
C8—H8B	0.9600
C2—S1—C5	91.06 (8)	C4—C9—H9B	109.5
C6—O3—C7	116.03 (14)	H9A—C9—H9B	109.5
C2—N1—C12	129.39 (17)	C4—C9—H9C	109.5
C2—N1—H1A	111.3 (15)	H9A—C9—H9C	109.5
C12—N1—H1A	118.8 (15)	H9B—C9—H9C	109.5
N1—C2—C3	124.72 (16)	O1—C10—C3	120.70 (17)
N1—C2—S1	122.77 (13)	O1—C10—C11	116.71 (17)
C3—C2—S1	112.47 (12)	C3—C10—C11	122.59 (17)
C2—C3—C4	111.16 (15)	C10—C11—H11A	109.5
C2—C3—C10	119.78 (15)	C10—C11—H11B	109.5
C4—C3—C10	128.91 (15)	H11A—C11—H11B	109.5
C5—C4—C3	112.44 (14)	C10—C11—H11C	109.5
C5—C4—C9	121.66 (16)	H11A—C11—H11C	109.5
C3—C4—C9	125.89 (16)	H11B—C11—H11C	109.5
C4—C5—C6	129.30 (15)	C13—C12—C17	119.32 (16)
C4—C5—S1	112.85 (13)	C13—C12—N1	123.40 (16)
C6—C5—S1	117.80 (13)	C17—C12—N1	117.20 (17)
O2—C6—O3	123.37 (17)	C12—C13—C14	119.95 (18)
O2—C6—C5	126.39 (17)	C12—C13—H13A	120.0
O3—C6—C5	110.24 (14)	C14—C13—H13A	120.0
O3—C7—C8	106.38 (17)	C15—C14—C13	120.5 (2)
O3—C7—H7A	110.5	C15—C14—H14A	119.8
C8—C7—H7A	110.5	C13—C14—H14A	119.8
O3—C7—H7B	110.5	C14—C15—C16	119.61 (19)
C8—C7—H7B	110.5	C14—C15—H15A	120.2
H7A—C7—H7B	108.6	C16—C15—H15A	120.2
C7—C8—H8A	109.5	C15—C16—C17	120.50 (19)
C7—C8—H8B	109.5	C15—C16—H16A	119.7
H8A—C8—H8B	109.5	C17—C16—H16A	119.7
C7—C8—H8C	109.5	C16—C17—C12	120.15 (19)
H8A—C8—H8C	109.5	C16—C17—H17A	119.9
H8B—C8—H8C	109.5	C12—C17—H17A	119.9
C4—C9—H9A	109.5
C12—N1—C2—C3	174.03 (18)	C4—C5—C6—O2	3.2 (3)
C12—N1—C2—S1	−3.6 (3)	S1—C5—C6—O2	−179.74 (17)
C5—S1—C2—N1	176.62 (16)	C4—C5—C6—O3	−176.76 (17)
C5—S1—C2—C3	−1.28 (14)	S1—C5—C6—O3	0.3 (2)
N1—C2—C3—C4	−176.94 (17)	C6—O3—C7—C8	174.54 (18)
S1—C2—C3—C4	0.91 (19)	C2—C3—C10—O1	4.0 (3)
N1—C2—C3—C10	−1.0 (3)	C4—C3—C10—O1	179.20 (18)
S1—C2—C3—C10	176.89 (13)	C2—C3—C10—C11	−175.38 (17)
C2—C3—C4—C5	0.1 (2)	C4—C3—C10—C11	−0.2 (3)
C10—C3—C4—C5	−175.39 (17)	C2—N1—C12—C13	39.8 (3)
C2—C3—C4—C9	−179.55 (16)	C2—N1—C12—C17	−143.5 (2)
C10—C3—C4—C9	4.9 (3)	C17—C12—C13—C14	−0.1 (3)
C3—C4—C5—C6	176.08 (18)	N1—C12—C13—C14	176.61 (18)
C9—C4—C5—C6	−4.2 (3)	C12—C13—C14—C15	−0.7 (3)
C3—C4—C5—S1	−1.09 (19)	C13—C14—C15—C16	0.8 (4)
C9—C4—C5—S1	178.60 (14)	C14—C15—C16—C17	−0.2 (4)
C2—S1—C5—C4	1.37 (14)	C15—C16—C17—C12	−0.6 (3)
C2—S1—C5—C6	−176.16 (15)	C13—C12—C17—C16	0.7 (3)
C7—O3—C6—O2	−2.5 (3)	N1—C12—C17—C16	−176.19 (19)
C7—O3—C6—C5	177.47 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (3)	1.93 (3)	2.607 (3)	140 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.82 (3)	1.93 (3)	2.607 (3)	140 (2)