Ethyl 2-benzamido-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carboxyl­ate

Mukhtar, A.; Tahir, M.N.; Khan, M.A.; Khan, M.N.

doi:10.1107/S1600536810037761

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2652

doi:10.1107/S1600536810037761

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Ethyl 2-benzamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Asma Mukhtar,^a M. Nawaz Tahir,^b ^* Misbahul Ain Khan ^a and Muhammad Naeem Khan ^c

^aInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 September 2010; accepted 21 September 2010; online 30 September 2010)

The molecule of the title compound, C₁₈H₁₉NO₃S, adopts an approximately planar conformation: the thiophene and phenyl rings form a dihedral angle of 8.13 (11)° while the ethyl ester group (r.m.s. deviation = 0.0217 Å) is inclined at 1.25 (14) and 8.61 (13)°, respectively, to the thiophene and phenyl rings. An intramolecular N—H⋯O hydrogen bond with an S(6) ring motif occurs as well as an intramolecular S⋯O hypervalent interaction [S⋯O = 2.7369 (18) Å]. The cyclohexene ring adopts a half-chair conformation and is disordered over two positions with site occupation factors of 0.641 (6) and 0.359 (6). In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(10) loops.

Related literature

For background on thiophene derivatives, see: Dupin et al. (2002 ); Khan & Rolim (1983 ); Sabnis et al. (1999 ). For related structures, see: Harrison et al. (2006 ); Yathirajan et al. (2007 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₉NO₃S
M_r = 329.40
Monoclinic, P 2₁ /c
a = 8.1061 (2) Å
b = 10.6593 (3) Å
c = 19.0554 (5) Å
β = 92.500 (1)°
V = 1644.92 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.953, T_max = 0.958
12204 measured reflections
2964 independent reflections
2052 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.01
2964 reflections
210 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.16 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—H1⋯O2	0.86	2.02	2.664 (2)	131
C6—H6⋯O1ⁱ	0.93	2.44	3.242 (3)	145
Symmetry code: (i) -x+2, -y+2, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536810037761/gk2302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037761/gk2302Isup2.hkl

checkCIF report

Comment top

Thiophenes and their condensed derivatives have been described in the literature (Khan & Rolim, 1983). Tetrahydro-1-benzothiophenes are intermediates for many useful products such as dyes and pharmaceuticals (Sabnis et al., 1999) and compounds containing thrombolytic activity (Dupin et al., 2002). The title compound (Fig. 1) has been prepared for the derivatization of other compounds.

The crystal structures of ethyl 2-acetylamino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (Harrison et al., 2006) and i.e. ethyl 2-(propionylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (Yathirajan et al., 2007) have been published which are related to the title compound.

In the title compound, the heterocyclic ring A (S1/C8/C9/C10/C15) and the phenyl ring B (C1—C6) are planar. The dihedral angle between A/B is 8.13 (11)°. The ethyl ester group C (O2/C16/O3/C17/C18) is planar with r. m. s. deviation of 0.0217 Å and is inclined at 1.25 (14) and 8.61 (13)° with the rings A and B, respectively. In the title compound an S(6) ring motif (Bernstein et al., 1995) is formed due to intramolecular H-bonding of N—H···O type (Table 1, Fig. 1). Two methylene groups of the cyclohexene ring in half-chair conformation are disordered over two positions with site occupation factors of 0.641 (6) and 0.359 (6).

Related literature top

For background on thiophene derivatives, see: Dupin et al. (2002); Khan & Rolim (1983); Sabnis et al. (1999). For related structures, see: Harrison et al. (2006); Yathirajan et al. (2007). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (0.3 g, 1.0 mmol) was dissolved in 10 ml of chloroform. To this solution 0.15 ml of benzoyl chloride was added and heated under reflux for 9 h. The solvent was removed and the residue was recrystallized from ethanol to affoard the colorless prism.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. The dotted line shows intramolecular hydrogen bonding.

Ethyl 2-benzamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate top

Crystal data top

C₁₈H₁₉NO₃S	F(000) = 696
M_r = 329.40	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2052 reflections
a = 8.1061 (2) Å	θ = 2.5–25.3°
b = 10.6593 (3) Å	µ = 0.21 mm⁻¹
c = 19.0554 (5) Å	T = 296 K
β = 92.500 (1)°	Prism, colorless
V = 1644.92 (8) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.953, T_max = 0.958	l = −22→22
12204 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0503P)² + 0.4332P] where P = (F_o² + 2F_c²)/3
2964 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.16 e Å⁻³
6 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₉NO₃S	V = 1644.92 (8) Å³
M_r = 329.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1061 (2) Å	µ = 0.21 mm⁻¹
b = 10.6593 (3) Å	T = 296 K
c = 19.0554 (5) Å	0.25 × 0.20 × 0.20 mm
β = 92.500 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2964 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2052 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.958	R_int = 0.037
12204 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	6 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
2964 reflections	Δρ_min = −0.20 e Å⁻³
210 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
S1	0.75739 (8)	0.64947 (6)	0.09851 (3)	0.0685 (2)
O1	0.9000 (2)	0.82309 (16)	0.01442 (9)	0.0875 (7)
O2	0.8026 (2)	0.41537 (14)	−0.09850 (7)	0.0658 (6)
O3	0.6816 (2)	0.26412 (14)	−0.03830 (7)	0.0666 (6)
N1	0.8625 (2)	0.63457 (16)	−0.03524 (8)	0.0527 (6)
C1	0.9770 (3)	0.8019 (2)	−0.10411 (11)	0.0545 (7)
C2	0.9702 (3)	0.7346 (2)	−0.16629 (12)	0.0679 (9)
C3	1.0262 (3)	0.7864 (3)	−0.22706 (13)	0.0781 (10)
C4	1.0909 (3)	0.9047 (3)	−0.22675 (14)	0.0804 (11)
C5	1.1013 (3)	0.9711 (3)	−0.16569 (16)	0.0830 (11)
C6	1.0438 (3)	0.9216 (2)	−0.10479 (13)	0.0697 (9)
C7	0.9121 (3)	0.7563 (2)	−0.03689 (12)	0.0582 (8)
C8	0.7865 (2)	0.5770 (2)	0.01970 (10)	0.0484 (7)
C9	0.7256 (2)	0.45660 (19)	0.01795 (10)	0.0464 (7)
C10	0.6520 (2)	0.4227 (2)	0.08292 (10)	0.0505 (7)
C11	0.5695 (3)	0.2999 (2)	0.09967 (11)	0.0615 (8)
C12A	0.5302 (8)	0.2864 (5)	0.1768 (3)	0.0771 (13)	0.641 (6)
C13A	0.4684 (7)	0.4071 (4)	0.2069 (3)	0.0771 (13)	0.641 (6)
C14	0.5952 (3)	0.5146 (3)	0.20270 (12)	0.0820 (10)
C15	0.6620 (3)	0.5167 (2)	0.12986 (11)	0.0601 (8)
C16	0.7408 (3)	0.3798 (2)	−0.04470 (11)	0.0518 (7)
C17	0.6953 (4)	0.1819 (2)	−0.09806 (13)	0.0804 (10)
C18	0.6130 (4)	0.0615 (3)	−0.08052 (16)	0.1017 (13)
C12B	0.4639 (11)	0.3191 (11)	0.1642 (4)	0.0771 (13)	0.359 (6)
C13B	0.5564 (13)	0.3883 (8)	0.2231 (4)	0.0771 (13)	0.359 (6)
H1	0.88006	0.58943	−0.07157	0.0632*
H4	1.12771	0.93963	−0.26797	0.0964*
H2	0.92751	0.65362	−0.16705	0.0815*
H3	1.01981	0.74051	−0.26860	0.0936*
H11A	0.64111	0.23142	0.08692	0.0738*
H11B	0.46774	0.29269	0.07120	0.0738*
H12A	0.44709	0.22178	0.18136	0.0926*	0.641 (6)
H12B	0.62887	0.26010	0.20338	0.0926*	0.641 (6)
H13A	0.44302	0.39369	0.25557	0.0926*	0.641 (6)
H13B	0.36703	0.43138	0.18147	0.0926*	0.641 (6)
H14A	0.54276	0.59409	0.21247	0.0985*
H14B	0.68476	0.50168	0.23738	0.0985*
H17A	0.81052	0.16736	−0.10724	0.0962*
H17B	0.64183	0.21915	−0.13955	0.0962*
H18A	0.66559	0.02642	−0.03888	0.1525*
H18B	0.62180	0.00366	−0.11881	0.1525*
H18C	0.49861	0.07682	−0.07259	0.1525*
H5	1.14776	1.05084	−0.16517	0.0996*
H6	1.04969	0.96880	−0.06371	0.0837*
H12C	0.36549	0.36616	0.15021	0.0926*	0.359 (6)
H12D	0.42929	0.23798	0.18130	0.0926*	0.359 (6)
H13C	0.48949	0.39036	0.26402	0.0926*	0.359 (6)
H13D	0.65770	0.34371	0.23564	0.0926*	0.359 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0836 (4)	0.0704 (4)	0.0522 (3)	−0.0085 (3)	0.0127 (3)	−0.0147 (3)
O1	0.1332 (16)	0.0676 (12)	0.0634 (10)	−0.0298 (11)	0.0243 (10)	−0.0167 (9)
O2	0.0950 (11)	0.0567 (10)	0.0472 (9)	−0.0046 (8)	0.0196 (8)	−0.0014 (7)
O3	0.0983 (12)	0.0495 (9)	0.0532 (9)	−0.0073 (8)	0.0168 (8)	−0.0036 (7)
N1	0.0610 (11)	0.0512 (11)	0.0463 (10)	−0.0008 (8)	0.0086 (8)	−0.0027 (8)
C1	0.0553 (12)	0.0529 (13)	0.0555 (13)	−0.0032 (10)	0.0045 (10)	0.0017 (11)
C2	0.0746 (15)	0.0689 (16)	0.0609 (14)	−0.0185 (12)	0.0098 (12)	−0.0028 (13)
C3	0.0868 (18)	0.089 (2)	0.0591 (15)	−0.0080 (15)	0.0115 (13)	−0.0011 (14)
C4	0.0936 (19)	0.0776 (19)	0.0714 (17)	0.0040 (15)	0.0196 (14)	0.0237 (16)
C5	0.101 (2)	0.0565 (16)	0.093 (2)	−0.0055 (14)	0.0221 (16)	0.0151 (15)
C6	0.0878 (17)	0.0550 (15)	0.0670 (15)	−0.0053 (12)	0.0108 (13)	0.0003 (12)
C7	0.0642 (14)	0.0529 (14)	0.0576 (13)	−0.0069 (11)	0.0053 (10)	−0.0027 (12)
C8	0.0476 (11)	0.0559 (13)	0.0418 (11)	0.0043 (10)	0.0031 (9)	−0.0007 (9)
C9	0.0489 (11)	0.0482 (12)	0.0420 (11)	0.0049 (9)	0.0025 (9)	0.0029 (9)
C10	0.0485 (12)	0.0593 (14)	0.0439 (11)	0.0080 (10)	0.0039 (9)	0.0047 (10)
C11	0.0621 (13)	0.0656 (15)	0.0576 (13)	0.0034 (11)	0.0117 (10)	0.0105 (11)
C12A	0.076 (3)	0.098 (2)	0.0587 (18)	0.004 (2)	0.0198 (18)	0.0171 (15)
C13A	0.076 (3)	0.098 (2)	0.0587 (18)	0.004 (2)	0.0198 (18)	0.0171 (15)
C14	0.0943 (18)	0.105 (2)	0.0479 (13)	0.0045 (16)	0.0172 (12)	−0.0045 (14)
C15	0.0626 (14)	0.0730 (16)	0.0452 (12)	0.0009 (11)	0.0096 (10)	−0.0011 (11)
C16	0.0594 (13)	0.0505 (13)	0.0456 (12)	0.0025 (10)	0.0044 (10)	0.0043 (10)
C17	0.127 (2)	0.0565 (15)	0.0587 (15)	−0.0111 (15)	0.0169 (14)	−0.0116 (12)
C18	0.154 (3)	0.0614 (18)	0.090 (2)	−0.0203 (18)	0.0097 (19)	−0.0084 (16)
C12B	0.076 (3)	0.098 (2)	0.0587 (18)	0.004 (2)	0.0198 (18)	0.0171 (15)
C13B	0.076 (3)	0.098 (2)	0.0587 (18)	0.004 (2)	0.0198 (18)	0.0171 (15)

Geometric parameters (Å, º) top

S1—C8	1.714 (2)	C13B—C14	1.440 (9)
S1—C15	1.732 (2)	C14—C15	1.512 (3)
O1—C7	1.217 (3)	C17—C18	1.491 (4)
O2—C16	1.221 (3)	C2—H2	0.9300
O3—C16	1.331 (3)	C3—H3	0.9300
O3—C17	1.445 (3)	C4—H4	0.9300
N1—C7	1.359 (3)	C5—H5	0.9300
N1—C8	1.381 (2)	C6—H6	0.9300
N1—H1	0.8600	C11—H11A	0.9700
C1—C2	1.384 (3)	C11—H11B	0.9700
C1—C6	1.386 (3)	C12A—H12A	0.9700
C1—C7	1.488 (3)	C12A—H12B	0.9700
C2—C3	1.378 (3)	C12B—H12D	0.9700
C3—C4	1.366 (4)	C12B—H12C	0.9700
C4—C5	1.361 (4)	C13A—H13B	0.9700
C5—C6	1.375 (4)	C13A—H13A	0.9700
C8—C9	1.375 (3)	C13B—H13C	0.9700
C9—C10	1.444 (3)	C13B—H13D	0.9700
C9—C16	1.457 (3)	C14—H14A	0.9700
C10—C15	1.343 (3)	C14—H14B	0.9700
C10—C11	1.510 (3)	C17—H17A	0.9700
C11—C12A	1.524 (6)	C17—H17B	0.9700
C11—C12B	1.542 (8)	C18—H18B	0.9600
C12A—C13A	1.503 (7)	C18—H18C	0.9600
C12B—C13B	1.514 (12)	C18—H18A	0.9600
C13A—C14	1.544 (6)

C8—S1—C15	90.83 (10)	C1—C6—H6	120.00
C16—O3—C17	116.70 (17)	C5—C6—H6	120.00
C7—N1—C8	125.72 (18)	C10—C11—H11A	109.00
C7—N1—H1	117.00	C10—C11—H11B	109.00
C8—N1—H1	117.00	C12A—C11—H11A	109.00
C2—C1—C6	118.0 (2)	C12A—C11—H11B	109.00
C2—C1—C7	124.4 (2)	H11A—C11—H11B	108.00
C6—C1—C7	117.5 (2)	C12B—C11—H11A	131.00
C1—C2—C3	120.6 (2)	C12B—C11—H11B	88.00
C2—C3—C4	120.5 (2)	C11—C12A—H12A	109.00
C3—C4—C5	119.6 (3)	C11—C12A—H12B	109.00
C4—C5—C6	120.8 (3)	C13A—C12A—H12A	109.00
C1—C6—C5	120.5 (2)	C13A—C12A—H12B	109.00
O1—C7—C1	123.0 (2)	H12A—C12A—H12B	108.00
O1—C7—N1	120.4 (2)	C13B—C12B—H12C	109.00
N1—C7—C1	116.61 (19)	C11—C12B—H12C	109.00
S1—C8—C9	112.26 (14)	C11—C12B—H12D	109.00
S1—C8—N1	123.14 (16)	C13B—C12B—H12D	109.00
N1—C8—C9	124.60 (18)	H12C—C12B—H12D	108.00
C8—C9—C16	120.08 (17)	C12A—C13A—H13A	109.00
C10—C9—C16	127.95 (18)	C14—C13A—H13A	109.00
C8—C9—C10	111.98 (17)	C14—C13A—H13B	109.00
C11—C10—C15	121.34 (18)	C12A—C13A—H13B	109.00
C9—C10—C11	126.98 (18)	H13A—C13A—H13B	108.00
C9—C10—C15	111.67 (19)	C14—C13B—H13C	109.00
C10—C11—C12B	108.7 (5)	C14—C13B—H13D	109.00
C10—C11—C12A	113.5 (3)	C12B—C13B—H13C	109.00
C11—C12A—C13A	112.0 (4)	C12B—C13B—H13D	109.00
C11—C12B—C13B	112.4 (7)	H13C—C13B—H13D	108.00
C12A—C13A—C14	112.4 (4)	C13A—C14—H14A	110.00
C12B—C13B—C14	111.2 (7)	C13A—C14—H14B	110.00
C13A—C14—C15	108.9 (3)	C15—C14—H14A	110.00
C13B—C14—C15	110.7 (4)	C13B—C14—H14A	131.00
S1—C15—C10	113.26 (16)	C13B—C14—H14B	81.00
S1—C15—C14	120.80 (18)	C15—C14—H14B	110.00
C10—C15—C14	125.9 (2)	H14A—C14—H14B	108.00
O2—C16—C9	124.47 (19)	C18—C17—H17A	110.00
O3—C16—C9	113.69 (18)	O3—C17—H17A	110.00
O2—C16—O3	121.84 (19)	O3—C17—H17B	110.00
O3—C17—C18	107.2 (2)	H17A—C17—H17B	109.00
C1—C2—H2	120.00	C18—C17—H17B	110.00
C3—C2—H2	120.00	C17—C18—H18C	109.00
C2—C3—H3	120.00	C17—C18—H18B	109.00
C4—C3—H3	120.00	H18B—C18—H18C	109.00
C3—C4—H4	120.00	H18A—C18—H18B	109.00
C5—C4—H4	120.00	H18A—C18—H18C	109.00
C4—C5—H5	120.00	C17—C18—H18A	109.00
C6—C5—H5	120.00

C15—S1—C8—N1	179.88 (17)	S1—C8—C9—C10	0.33 (19)
C15—S1—C8—C9	−0.02 (15)	S1—C8—C9—C16	−179.36 (15)
C8—S1—C15—C10	−0.32 (18)	N1—C8—C9—C10	−179.57 (16)
C8—S1—C15—C14	−178.7 (2)	N1—C8—C9—C16	0.8 (3)
C17—O3—C16—O2	0.5 (3)	C8—C9—C10—C11	178.53 (18)
C17—O3—C16—C9	−178.9 (2)	C8—C9—C10—C15	−0.6 (2)
C16—O3—C17—C18	−176.8 (2)	C16—C9—C10—C11	−1.8 (3)
C8—N1—C7—O1	4.4 (3)	C16—C9—C10—C15	179.1 (2)
C8—N1—C7—C1	−174.38 (19)	C8—C9—C16—O2	−1.6 (3)
C7—N1—C8—S1	−5.3 (3)	C8—C9—C16—O3	177.88 (18)
C7—N1—C8—C9	174.55 (19)	C10—C9—C16—O2	178.8 (2)
C6—C1—C2—C3	−0.9 (4)	C10—C9—C16—O3	−1.8 (3)
C7—C1—C2—C3	176.9 (2)	C9—C10—C11—C12A	170.4 (3)
C2—C1—C6—C5	0.0 (4)	C15—C10—C11—C12A	−10.6 (4)
C7—C1—C6—C5	−178.0 (2)	C9—C10—C15—S1	0.6 (2)
C2—C1—C7—O1	−170.1 (2)	C9—C10—C15—C14	178.9 (2)
C2—C1—C7—N1	8.6 (3)	C11—C10—C15—S1	−178.60 (16)
C6—C1—C7—O1	7.7 (4)	C11—C10—C15—C14	−0.3 (3)
C6—C1—C7—N1	−173.6 (2)	C10—C11—C12A—C13A	39.9 (5)
C1—C2—C3—C4	0.7 (4)	C11—C12A—C13A—C14	−59.8 (6)
C2—C3—C4—C5	0.6 (4)	C12A—C13A—C14—C15	46.7 (5)
C3—C4—C5—C6	−1.6 (4)	C13A—C14—C15—S1	160.7 (3)
C4—C5—C6—C1	1.3 (4)	C13A—C14—C15—C10	−17.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.02	2.664 (2)	131
C6—H6···O1ⁱ	0.93	2.44	3.242 (3)	145
C11—H11A···O3	0.97	2.45	2.845 (3)	104

Symmetry code: (i) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₃S
M_r	329.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.1061 (2), 10.6593 (3), 19.0554 (5)
β (°)	92.500 (1)
V (Å³)	1644.92 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.953, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	12204, 2964, 2052
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.01
No. of reflections	2964
No. of parameters	210
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.02	2.664 (2)	131
C6—H6···O1ⁱ	0.93	2.44	3.242 (3)	145

Symmetry code: (i) −x+2, −y+2, −z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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