2-Amino-N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]acetamide

Fun, H.-K.; Chantrapromma, S.; Dayananda, A.S.; Yathirajan, H.S.; Ramesha, A.R.

doi:10.1107/S1600536812003261

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o547-o548

doi:10.1107/S1600536812003261

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2-Amino-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]acetamide

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma,^b § A. S. Dayananda,^c H. S. Yathirajan ^c and A. R. Ramesha ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dR. L. Fine Chem, Bangalore 560 064, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 January 2012; accepted 25 January 2012; online 31 January 2012)

In the title compound, C₁₅H₁₅ClN₂O₂S, the 2-aminoacetamide N—C(=O)—C—N unit is approximately planar, with an r.m.s. deviation of 0.020 (4) Å. The central thiophene ring makes dihedral angles of 7.84 (11) and 88.11 (11)°, respectively, with the 2-aminoacetamide unit and the 2-chlorophenyl ring. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by an N—H⋯O hydrogen bond and weak C—H⋯O interactions into a chain along the c axis. A C—H⋯π interaction 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_r = 322.80
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.163
S = 1.05
4184 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003261/is5060sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812003261/is5060Isup3.cml

checkCIF report

Comment top

The title compound is an intermediate in the synthesis of a drug known as "etizolam" which possesses potent hypnotic properties (Nakamura & Mukasa, 1992). Thiophenes and their biheterocycles have received considerable attention during last two decades as they are endowed with variety of biological activities and have wide range of therapeutic properties (Gewald & Schindler, 1990; Ramanathan & Namboothiri, 1978). Thiophene derivatives possess different pharmacological and biological properties, of which the more potent properties are the anticonvulsant, anti-inflammatory and antibacterial activities (Jagadees Babu et al., 2011; Shafeeque et al., 1999). In view of the importance of thiophenes, the crystal structure of the title compound (I) is reported.

In the molecule of (I), C₁₅H₁₅ClN₂O₂S, the central thiophene ring makes a dihedral angle of 88.11 (11)° with the 2-chlorophenyl ring. The 2-aminoacetamide moiety is co-planar with the thiophene ring with an r.m.s. deviation of 0.067 (2) Å for the ten non-H atoms (C8–C11/C14-C15, S1, O2 N1 and N2) (Fig. 1) and with torsion angles C9–N1–C14–O2 = -1.6 (3)°, C9–N1–C14–C15 = 178.49 (18)° and N1–C14–C15–N2 = -6.9 (3)°. The orientation of the ethyl group with respect to the thiophene ring can be reflected by the torsion angle C11–C10–C12–C13 = 118.6 (4)° which indicates the (+)-anti-clinal conformation. An intramolecular N1—H1N1···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). Bond distances of (I) are in normal range (Allen et al., 1987) and comparable with the related structures (Dockendorff et al., 2006; Ferreira de Lima et al., 2009; Nogueira et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked by intermolecular N—H···O(acetamide) hydrogen bonds and weak C—H···O(acetamide) interactions (Table 1) into chains along the c axis. Weak C—H···π interactions are present (Table1).

Related literature top

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 top

The title compound was synthesized by the literature method (Nakanishi et al., 1973). Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from C₂H₅OH/DMSO (1:1 v/v) by slow evaporation of the solvent at room temperature after several days (m.p. 417–419 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular N—H···O hydrogen bond is shown as a dash line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, showing a chain running along the c axis. Hydrogen bonds are shown as dashed lines.

2-Amino-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]acetamide top

Crystal data top

C₁₅H₁₅ClN₂O₂S	F(000) = 672
M_r = 322.80	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.079P)² + 0.4642P] where P = (F_o² + 2F_c²)/3
4184 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₅ClN₂O₂S	V = 1578.8 (2) Å³
M_r = 322.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.9784 (11) Å	µ = 0.38 mm⁻¹
b = 13.5565 (11) Å	T = 293 K
c = 8.3334 (7) Å	0.56 × 0.41 × 0.28 mm
β = 91.233 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4184 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3180 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.902	R_int = 0.020
16034 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	Δρ_max = 0.47 e Å⁻³
4184 reflections	Δρ_min = −0.28 e Å⁻³
191 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅ClN₂O₂S
M_r	322.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.9784 (11), 13.5565 (11), 8.3334 (7)
β (°)	91.233 (1)
V (Å³)	1578.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.56 × 0.41 × 0.28

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.817, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	16034, 4184, 3180
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.163, 1.05
No. of reflections	4184
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) −x, −y, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

ASD thanks the University of Mysore for research facilities. SC thanks the Prince of Songkla University for generous support. The authors thank the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

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Volume 68| Part 2| February 2012| Pages o547-o548

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