2-Amino-N-[3-(2-chloro-benzo-yl)-5-ethyl-thio-phen-2-yl]acetamide.

In the title compound, C(15)H(15)ClN(2)O(2)S, the 2-amino-acetamide N-C(=O)-C-N unit is approximately planar, with an r.m.s. deviation of 0.020 (4) Å. The central thio-phene ring makes dihedral angles of 7.84 (11) and 88.11 (11)°, respectively, with the 2-amino-acetamide unit and the 2-chloro-phenyl ring. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by an N-H⋯O hydrogen bond and weak C-H⋯O inter-actions into a chain along the c axis. A C-H⋯π inter-action is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and activities of etizolam and thio­phene derivatives, see: Gewald & Schindler (1990 ▶); Jagadees Babu et al. (2011 ▶); Shafeeque et al. (1999 ▶); Nakamura & Mukasa (1992 ▶); Nakanishi et al. (1973 ▶); Ramanathan & Namboothiri (1978 ▶). For related structures, see: Dockendorff et al. (2006 ▶); Ferreira de Lima et al. (2009 ▶); Nogueira et al. (2010 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H15ClN2O2S

M = 322.80

Monoclinic,

a = 13.9784 (11) Å

b = 13.5565 (11) Å

c = 8.3334 (7) Å

β = 91.233 (1)°

V = 1578.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.56 × 0.41 × 0.28 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.817, T max = 0.902

16034 measured reflections

4184 independent reflections

3180 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.163

S = 1.05

4184 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003261/is5060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003261/is5060Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003261/is5060Isup3.cml

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

C15H15ClN2O2S	F(000) = 672
Mr = 322.80	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Melting point = 417–419 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.9784 (11) Å	Cell parameters from 4184 reflections
b = 13.5565 (11) Å	θ = 1.5–29.0°
c = 8.3334 (7) Å	µ = 0.38 mm−1
β = 91.233 (1)°	T = 293 K
V = 1578.8 (2) Å3	Block, yellow
Z = 4	0.56 × 0.41 × 0.28 mm

Bruker APEX DUO CCD area-detector diffractometer	4184 independent reflections
Radiation source: sealed tube	3180 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→19
Tmin = 0.817, Tmax = 0.902	k = −18→17
16034 measured reflections	l = −11→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.079P)2 + 0.4642P] where P = (Fo2 + 2Fc2)/3
4184 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.44203 (5)	0.00271 (7)	0.78182 (12)	0.1059 (3)
S1	0.12494 (4)	0.13080 (4)	1.17920 (6)	0.06549 (19)
O1	0.19142 (11)	−0.04825 (14)	0.72869 (17)	0.0736 (5)
O2	−0.03578 (13)	0.17865 (14)	1.0035 (2)	0.0834 (5)
N1	0.06864 (11)	0.08376 (12)	0.87282 (19)	0.0516 (4)
H1N1	0.0845	0.0597	0.7864	0.062*
N2	−0.02762 (16)	0.09813 (17)	0.5929 (3)	0.0771 (5)
H1N2	−0.0804	0.0735	0.5496	0.093*
H2N2	−0.0066	0.1416	0.5262	0.093*
C1	0.40677 (15)	−0.11245 (19)	0.8517 (3)	0.0658 (5)
C2	0.47451 (19)	−0.1860 (3)	0.8745 (3)	0.0863 (8)
H2A	0.5387	−0.1741	0.8543	0.104*
C3	0.4451 (2)	−0.2771 (2)	0.9274 (3)	0.0897 (8)
H3A	0.4899	−0.3274	0.9402	0.108*
C4	0.3506 (2)	−0.2951 (2)	0.9617 (3)	0.0834 (7)
H4A	0.3319	−0.3566	0.9988	0.100*
C5	0.28426 (17)	−0.22083 (18)	0.9404 (3)	0.0694 (6)
H5A	0.2206	−0.2324	0.9645	0.083*
C6	0.31130 (13)	−0.12879 (15)	0.8834 (2)	0.0545 (4)
C7	0.23554 (13)	−0.05129 (16)	0.8577 (2)	0.0540 (4)
C8	0.21449 (13)	0.01234 (14)	0.9924 (2)	0.0506 (4)
C9	0.13424 (13)	0.07179 (14)	0.9968 (2)	0.0497 (4)
C10	0.23183 (18)	0.07790 (18)	1.2498 (3)	0.0677 (6)
C11	0.26932 (16)	0.01788 (16)	1.1402 (2)	0.0606 (5)
H11A	0.3258	−0.0171	1.1580	0.073*
C12	0.2683 (3)	0.1027 (3)	1.4170 (3)	0.1028 (10)
H12A	0.2203	0.0829	1.4930	0.123*
H12B	0.3253	0.0639	1.4394	0.123*
C13	0.2909 (3)	0.2061 (3)	1.4438 (5)	0.1304 (15)
H13A	0.3160	0.2147	1.5510	0.196*
H13B	0.2339	0.2450	1.4296	0.196*
H13C	0.3378	0.2270	1.3684	0.196*
C14	−0.01269 (14)	0.13727 (14)	0.8807 (3)	0.0568 (4)
C15	−0.07268 (15)	0.14234 (17)	0.7292 (3)	0.0642 (5)
H15A	−0.1331	0.1092	0.7468	0.077*
H15B	−0.0865	0.2109	0.7050	0.077*

	U11	U22	U33	U12	U13	U23
Cl1	0.0672 (4)	0.1184 (7)	0.1321 (7)	−0.0118 (4)	0.0012 (4)	0.0488 (5)
S1	0.0777 (4)	0.0644 (3)	0.0544 (3)	−0.0016 (2)	0.0008 (2)	−0.0138 (2)
O1	0.0712 (9)	0.1004 (12)	0.0487 (7)	0.0291 (9)	−0.0113 (6)	−0.0111 (7)
O2	0.0772 (11)	0.0864 (12)	0.0864 (11)	0.0238 (9)	0.0016 (9)	−0.0235 (10)
N1	0.0509 (8)	0.0529 (9)	0.0509 (8)	0.0057 (7)	−0.0018 (6)	−0.0039 (6)
N2	0.0811 (13)	0.0784 (13)	0.0710 (12)	0.0116 (11)	−0.0191 (10)	−0.0050 (10)
C1	0.0517 (10)	0.0825 (15)	0.0631 (12)	0.0085 (10)	−0.0008 (9)	0.0073 (11)
C2	0.0599 (13)	0.119 (2)	0.0801 (16)	0.0295 (14)	−0.0003 (11)	0.0058 (16)
C3	0.095 (2)	0.0887 (19)	0.0849 (17)	0.0402 (16)	−0.0130 (14)	−0.0049 (15)
C4	0.099 (2)	0.0647 (14)	0.0851 (17)	0.0086 (13)	−0.0192 (14)	−0.0007 (12)
C5	0.0655 (13)	0.0703 (14)	0.0720 (13)	−0.0003 (10)	−0.0114 (10)	0.0000 (11)
C6	0.0497 (9)	0.0654 (12)	0.0483 (9)	0.0070 (8)	−0.0045 (7)	−0.0031 (8)
C7	0.0470 (9)	0.0654 (11)	0.0494 (9)	0.0045 (8)	−0.0027 (7)	0.0002 (8)
C8	0.0477 (9)	0.0560 (10)	0.0478 (9)	−0.0027 (7)	−0.0047 (7)	−0.0009 (7)
C9	0.0518 (9)	0.0492 (9)	0.0480 (9)	−0.0050 (7)	−0.0003 (7)	−0.0030 (7)
C10	0.0822 (14)	0.0698 (13)	0.0505 (10)	−0.0120 (11)	−0.0132 (10)	−0.0024 (9)
C11	0.0608 (11)	0.0649 (12)	0.0555 (10)	−0.0065 (9)	−0.0135 (9)	0.0017 (9)
C12	0.129 (3)	0.121 (2)	0.0574 (13)	−0.024 (2)	−0.0235 (15)	−0.0127 (15)
C13	0.131 (3)	0.144 (3)	0.114 (3)	0.016 (2)	−0.040 (2)	−0.072 (3)
C14	0.0534 (10)	0.0485 (10)	0.0686 (12)	0.0021 (8)	0.0015 (9)	−0.0005 (9)
C15	0.0538 (11)	0.0601 (12)	0.0784 (14)	0.0042 (9)	−0.0054 (9)	0.0132 (10)

Cl1—C1	1.741 (3)	C5—C6	1.390 (3)
S1—C9	1.7248 (18)	C5—H5A	0.9300
S1—C10	1.748 (3)	C6—C7	1.504 (3)
O1—C7	1.229 (2)	C7—C8	1.451 (3)
O2—C14	1.217 (3)	C8—C9	1.382 (3)
N1—C14	1.351 (2)	C8—C11	1.438 (3)
N1—C9	1.376 (2)	C10—C11	1.338 (3)
N1—H1N1	0.8253	C10—C12	1.511 (3)
N2—C15	1.441 (3)	C11—H11A	0.9300
N2—H1N2	0.8805	C12—C13	1.454 (5)
N2—H2N2	0.8655	C12—H12A	0.9700
C1—C6	1.384 (3)	C12—H12B	0.9700
C1—C2	1.386 (3)	C13—H13A	0.9600
C2—C3	1.376 (5)	C13—H13B	0.9600
C2—H2A	0.9300	C13—H13C	0.9600
C3—C4	1.379 (4)	C14—C15	1.502 (3)
C3—H3A	0.9300	C15—H15A	0.9700
C4—C5	1.378 (3)	C15—H15B	0.9700
C4—H4A	0.9300
C9—S1—C10	91.49 (10)	N1—C9—C8	125.22 (16)
C14—N1—C9	125.06 (17)	N1—C9—S1	123.04 (14)
C14—N1—H1N1	119.8	C8—C9—S1	111.74 (13)
C9—N1—H1N1	114.9	C11—C10—C12	129.4 (3)
C15—N2—H1N2	96.0	C11—C10—S1	111.37 (15)
C15—N2—H2N2	112.5	C12—C10—S1	119.2 (2)
H1N2—N2—H2N2	106.7	C10—C11—C8	114.0 (2)
C6—C1—C2	121.2 (2)	C10—C11—H11A	123.0
C6—C1—Cl1	119.25 (17)	C8—C11—H11A	123.0
C2—C1—Cl1	119.6 (2)	C13—C12—C10	115.1 (3)
C3—C2—C1	118.8 (3)	C13—C12—H12A	108.5
C3—C2—H2A	120.6	C10—C12—H12A	108.5
C1—C2—H2A	120.6	C13—C12—H12B	108.5
C2—C3—C4	121.2 (2)	C10—C12—H12B	108.5
C2—C3—H3A	119.4	H12A—C12—H12B	107.5
C4—C3—H3A	119.4	C12—C13—H13A	109.5
C5—C4—C3	119.3 (3)	C12—C13—H13B	109.5
C5—C4—H4A	120.3	H13A—C13—H13B	109.5
C3—C4—H4A	120.3	C12—C13—H13C	109.5
C4—C5—C6	120.8 (2)	H13A—C13—H13C	109.5
C4—C5—H5A	119.6	H13B—C13—H13C	109.5
C6—C5—H5A	119.6	O2—C14—N1	121.8 (2)
C1—C6—C5	118.6 (2)	O2—C14—C15	122.17 (19)
C1—C6—C7	122.7 (2)	N1—C14—C15	116.03 (18)
C5—C6—C7	118.68 (18)	N2—C15—C14	113.44 (17)
O1—C7—C8	123.42 (18)	N2—C15—H15A	108.9
O1—C7—C6	119.14 (18)	C14—C15—H15A	108.9
C8—C7—C6	117.31 (16)	N2—C15—H15B	108.9
C9—C8—C11	111.39 (17)	C14—C15—H15B	108.9
C9—C8—C7	123.05 (16)	H15A—C15—H15B	107.7
C11—C8—C7	125.47 (18)
C6—C1—C2—C3	1.0 (4)	C14—N1—C9—S1	−4.1 (3)
Cl1—C1—C2—C3	−179.0 (2)	C11—C8—C9—N1	178.71 (18)
C1—C2—C3—C4	−1.7 (4)	C7—C8—C9—N1	−4.8 (3)
C2—C3—C4—C5	0.9 (4)	C11—C8—C9—S1	−1.3 (2)
C3—C4—C5—C6	0.7 (4)	C7—C8—C9—S1	175.21 (15)
C2—C1—C6—C5	0.6 (3)	C10—S1—C9—N1	−178.53 (17)
Cl1—C1—C6—C5	−179.48 (17)	C10—S1—C9—C8	1.49 (16)
C2—C1—C6—C7	−179.0 (2)	C9—S1—C10—C11	−1.31 (19)
Cl1—C1—C6—C7	1.0 (3)	C9—S1—C10—C12	179.3 (2)
C4—C5—C6—C1	−1.4 (3)	C12—C10—C11—C8	−179.9 (3)
C4—C5—C6—C7	178.2 (2)	S1—C10—C11—C8	0.8 (3)
C1—C6—C7—O1	92.5 (3)	C9—C8—C11—C10	0.3 (3)
C5—C6—C7—O1	−87.0 (3)	C7—C8—C11—C10	−176.1 (2)
C1—C6—C7—C8	−91.3 (2)	C11—C10—C12—C13	118.6 (4)
C5—C6—C7—C8	89.1 (2)	S1—C10—C12—C13	−62.2 (4)
O1—C7—C8—C9	10.0 (3)	C9—N1—C14—O2	−1.6 (3)
C6—C7—C8—C9	−166.00 (18)	C9—N1—C14—C15	178.49 (18)
O1—C7—C8—C11	−174.0 (2)	O2—C14—C15—N2	173.2 (2)
C6—C7—C8—C11	10.0 (3)	N1—C14—C15—N2	−6.9 (3)
C14—N1—C9—C8	175.84 (19)

Cg1 is the centroid of the thiophene C8/C9/S1/C10/C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.83	2.15	2.771 (2)	132
N2—H2N2···O2i	0.87	2.48	3.118 (3)	131
C15—H15B···O2i	0.97	2.37	3.120 (3)	134
C15—H15A···Cg1ii	0.97	2.75	3.530 (2)	238

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thio­phene C8/C9/S1/C10/C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.83	2.15	2.771 (2)	132
N2—H2N2⋯O2i	0.87	2.48	3.118 (3)	131
C15—H15B⋯O2i	0.97	2.37	3.120 (3)	134
C15—H15A⋯Cg1ii	0.97	2.75	3.530 (2)	238

Symmetry codes: (i) ; (ii) .