Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carboxyl­ate

Mukhtar, A.; Tahir, M.N.; Khan, M.A.; Ather, A.Q.; Sajid, N.

doi:10.1107/S1600536812025251

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2041

https://doi.org/10.1107/S1600536812025251

Open

access

Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Asma Mukhtar,^a M. Nawaz Tahir,^b ^* Misbahul Ain Khan,^c Abdul Qayyum Ather ^d and Naveed Sajid ^c

^aInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, ^cDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, and ^dApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 3 June 2012; accepted 3 June 2012; online 13 June 2012)

In the title compound, C₁₇H₁₈N₂O₃S, the dihedral angles between the thiophene ring and the ethyl ester group and the pyridine-4-carboxamide unit are 7.1 (2) and 9.47 (11)°, respectively. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds between the tetrahydro-1-benzothiophene and the pyridine-4-carboxamide residues generate R₂²(16) loops. There exists positional disorder in three methelene groups of the cyclohexane ring and the terminal C atom of the ethyl ester side chain in a 0.691 (14):0.309 (14) occupancy ratio.

Related literature

For related structures, see: Mukhtar et al. (2010a ,b ).

Experimental

Crystal data

C₁₇H₁₈N₂O₃S
M_r = 330.39
Triclinic, $[P \overline 1]$
a = 8.5604 (6) Å
b = 9.3481 (7) Å
c = 11.7443 (10) Å
α = 105.121 (3)°
β = 99.748 (2)°
γ = 110.806 (3)°
V = 811.59 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.953, T_max = 0.958
12176 measured reflections
2914 independent reflections
1842 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.00
2914 reflections
243 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 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	1.99	2.650 (3)	132
C7A—H7A⋯O3ⁱ	0.97	2.56	3.323 (12)	136
Symmetry code: (i) -x+1, -y, -z+1.

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 global, I. DOI: https://doi.org/10.1107/S1600536812025251/hb6838sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025251/hb6838Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025251/hb6838Isup3.cml

checkCIF report

Comment top

We reported the crystal structures of ethyl 2-benzamido-4,5,6,7-tetrahydro-1- benzothiophene-3-carboxylate (Mukhtar et al., 2010a) and diethyl 5-acetamido-3-methylthiophene-2,4-dicarboxylate (Mukhtar et al., 2010b) which are related to the tile compound (I), (Fig. 1).

In (I), the thiophene ring A (S1/C8/C3/C2/C9), ethyl ester group B (O1/C1/O2/C16/C17A) and pyridine-4-carboxamide moiety C (C10—C15/N1/N2/O3) are planar with r. m. s. deviation of 0.0010, 0.0906 and 0.0520 Å, respectively. The dihedral angle between A/B, A/C and B/C is 7.07 (21), 9.47 (11) and 3.30 (20)°, respectively. In the title compound an S(6) ring motif is formed due to intramolecular H-bonding of N—H···O type (Table 1, Fig. 1). The molecules are linked in the form of dimers with R₂²(16) ring motif due to C—H···O type of H-bonding (Table 1, Fig. 2). Three methelene groups of cyclohexane ring and terminal C-atom of ethyl ester are disordered over two set of sites with occupancy ratio of 0.691 (14):0.309 (14).

Related literature top

For related structures, see: Mukhtar et al. (2010a,b).

Experimental top

A mixture of (0.4 g, 3 mmol) of pyridine-4-carboxylic acid and 0.5 ml of thionyl chloride was heated for 5 minutes. Ethyl 2-pyridyl-4-amido-4,5,6,7- tetrahydro-1-benzothiophene-3-carboxylate (0.7 g, 3 mmol) was dissolved in 30 ml chloroform separately and then added to the former mixture. The whole reaction mixture was refluxed for 45 minutes. The solvent was removed and residue was recrystallized in acetone to give colorless prisms of (I). M.p.: 431 K, yield: 0.92 g, 80%.

Structure description top

For related structures, see: Mukhtar et al. (2010a,b).

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 displacement ellipsoids drawn at the 50% probability level. The dotted line show intramolecular H-bonding.
	Fig. 2. The partial packing, which shows that molecules form dimers with R₂²(16) ring.

Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetrahydro-1-benzothiophene- 3-carboxylate top

Crystal data top

C₁₇H₁₈N₂O₃S	Z = 2
M_r = 330.39	F(000) = 384
Triclinic, P1	D_x = 1.352 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5604 (6) Å	Cell parameters from 1842 reflections
b = 9.3481 (7) Å	θ = 2.5–25.3°
c = 11.7443 (10) Å	µ = 0.22 mm⁻¹
α = 105.121 (3)°	T = 296 K
β = 99.748 (2)°	Prism, colorless
γ = 110.806 (3)°	0.24 × 0.18 × 0.15 mm
V = 811.59 (11) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2914 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.5°
ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.953, T_max = 0.958	l = −14→14
12176 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.049P)² + 0.1304P] where P = (F_o² + 2F_c²)/3
2914 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.15 e Å⁻³
10 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₃S	γ = 110.806 (3)°
M_r = 330.39	V = 811.59 (11) Å³
Triclinic, P1	Z = 2
a = 8.5604 (6) Å	Mo Kα radiation
b = 9.3481 (7) Å	µ = 0.22 mm⁻¹
c = 11.7443 (10) Å	T = 296 K
α = 105.121 (3)°	0.24 × 0.18 × 0.15 mm
β = 99.748 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2914 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1842 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.958	R_int = 0.039
12176 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	10 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
2914 reflections	Δρ_min = −0.18 e Å⁻³
243 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	0.57947 (9)	0.19759 (8)	0.46283 (7)	0.0767 (3)
O1	0.6976 (2)	0.68634 (18)	0.35270 (15)	0.0742 (6)
O2	0.8949 (2)	0.73080 (19)	0.52291 (15)	0.0730 (6)
O3	0.8381 (3)	0.2881 (3)	0.68270 (19)	0.1003 (8)
N1	0.8635 (2)	0.4829 (2)	0.60071 (17)	0.0615 (7)
N2	1.3610 (3)	0.7692 (4)	0.9953 (2)	0.0968 (11)
C1	0.7620 (3)	0.6392 (3)	0.4390 (2)	0.0580 (8)
C2	0.6600 (3)	0.4677 (3)	0.42082 (19)	0.0517 (8)
C3	0.5015 (3)	0.3510 (3)	0.3252 (2)	0.0568 (8)
C4	0.4040 (3)	0.3808 (3)	0.2210 (2)	0.0684 (9)
C5A	0.2613 (14)	0.2210 (11)	0.1232 (9)	0.084 (3)	0.691 (14)
C6A	0.1643 (9)	0.1068 (9)	0.1818 (7)	0.090 (2)	0.691 (14)
C7A	0.2885 (14)	0.0544 (12)	0.2537 (10)	0.093 (5)	0.691 (14)
C8	0.4453 (3)	0.2032 (3)	0.3374 (2)	0.0647 (9)
C9	0.7149 (3)	0.3990 (3)	0.5005 (2)	0.0571 (8)
C10	0.9163 (3)	0.4265 (3)	0.6877 (2)	0.0681 (10)
C11	1.0748 (3)	0.5483 (3)	0.7916 (2)	0.0624 (9)
C12	1.1234 (4)	0.5047 (4)	0.8909 (3)	0.0915 (12)
C13	1.2663 (5)	0.6197 (5)	0.9893 (3)	0.1068 (16)
C14	1.3131 (4)	0.8068 (4)	0.8988 (3)	0.0810 (11)
C15	1.1737 (3)	0.7024 (3)	0.7966 (2)	0.0690 (10)
C16	0.7948 (4)	0.8546 (3)	0.3616 (3)	0.0935 (11)
C17A	0.7281 (10)	0.8628 (10)	0.2439 (6)	0.113 (3)	0.691 (14)
C5B	0.221 (2)	0.242 (2)	0.159 (3)	0.083 (7)	0.310 (14)
C6B	0.225 (2)	0.0756 (16)	0.1323 (18)	0.091 (6)	0.310 (14)
C7B	0.275 (3)	0.054 (2)	0.2566 (18)	0.074 (8)	0.310 (14)
C17B	0.687 (2)	0.894 (2)	0.2657 (6)	0.103 (5)	0.310 (14)
H4A	0.48597	0.43620	0.18225	0.0821*
H4B	0.35058	0.45180	0.25392	0.0821*
H1	0.92888	0.58106	0.60821	0.0738*
H7A	0.23001	−0.00598	0.30131	0.1119*	0.691 (14)
H7B	0.32310	−0.01579	0.19682	0.1119*	0.691 (14)
H12	1.06183	0.40089	0.89190	0.1100*
H13	1.29763	0.58902	1.05578	0.1283*
H14	1.37777	0.91097	0.89972	0.0972*
H15	1.14681	0.73660	0.73125	0.0828*
H16A	0.77654	0.92982	0.42663	0.1120*
H16B	0.91878	0.88177	0.37895	0.1120*
H17A	0.60304	0.82038	0.22283	0.1699*	0.691 (14)
H17B	0.76116	0.79910	0.18235	0.1699*	0.691 (14)
H17C	0.77538	0.97428	0.24783	0.1699*	0.691 (14)
H5A	0.17977	0.24607	0.07281	0.1004*	0.691 (14)
H5B	0.31459	0.16809	0.06985	0.1004*	0.691 (14)
H6A	0.06979	0.01117	0.11859	0.1079*	0.691 (14)
H6B	0.11397	0.16052	0.23733	0.1079*	0.691 (14)
H5C	0.14711	0.25201	0.21193	0.0997*	0.310 (14)
H5D	0.17039	0.25150	0.08217	0.0997*	0.310 (14)
H6C	0.31023	0.06938	0.08848	0.1103*	0.310 (14)
H6D	0.11147	−0.00965	0.08180	0.1103*	0.310 (14)
H7C	0.29232	−0.04536	0.24441	0.0886*	0.310 (14)
H7D	0.18307	0.04701	0.29589	0.0886*	0.310 (14)
H17D	0.56995	0.86379	0.27276	0.1534*	0.310 (14)
H17E	0.68253	0.83476	0.18437	0.1534*	0.310 (14)
H17F	0.73952	1.00931	0.28019	0.1534*	0.310 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0865 (5)	0.0500 (4)	0.0840 (5)	0.0152 (3)	0.0208 (4)	0.0297 (3)
O1	0.0827 (12)	0.0456 (10)	0.0725 (11)	0.0125 (9)	−0.0016 (9)	0.0224 (8)
O2	0.0732 (11)	0.0510 (10)	0.0704 (11)	0.0079 (9)	−0.0004 (10)	0.0225 (9)
O3	0.1113 (16)	0.0709 (13)	0.1059 (15)	0.0190 (12)	0.0106 (12)	0.0512 (12)
N1	0.0666 (13)	0.0511 (12)	0.0605 (12)	0.0171 (10)	0.0133 (10)	0.0238 (10)
N2	0.0930 (19)	0.110 (2)	0.0823 (17)	0.0380 (17)	0.0115 (14)	0.0410 (16)
C1	0.0664 (16)	0.0493 (14)	0.0562 (14)	0.0225 (13)	0.0151 (13)	0.0193 (12)
C2	0.0573 (14)	0.0414 (13)	0.0528 (13)	0.0167 (11)	0.0177 (11)	0.0152 (10)
C3	0.0581 (14)	0.0496 (14)	0.0562 (14)	0.0177 (12)	0.0194 (12)	0.0133 (11)
C4	0.0658 (16)	0.0581 (15)	0.0681 (16)	0.0203 (13)	0.0112 (13)	0.0147 (12)
C5A	0.074 (4)	0.073 (5)	0.076 (6)	0.019 (3)	0.003 (3)	0.012 (3)
C6A	0.067 (4)	0.072 (4)	0.085 (4)	0.000 (3)	0.003 (3)	0.008 (3)
C7A	0.090 (9)	0.074 (8)	0.098 (9)	0.010 (6)	0.028 (7)	0.037 (6)
C8	0.0640 (16)	0.0470 (15)	0.0688 (16)	0.0117 (13)	0.0176 (13)	0.0156 (12)
C9	0.0635 (15)	0.0458 (13)	0.0590 (14)	0.0177 (12)	0.0229 (13)	0.0178 (12)
C10	0.0803 (18)	0.0627 (17)	0.0696 (17)	0.0299 (15)	0.0245 (14)	0.0343 (14)
C11	0.0681 (16)	0.0712 (18)	0.0609 (15)	0.0365 (14)	0.0223 (13)	0.0306 (13)
C12	0.096 (2)	0.098 (2)	0.086 (2)	0.0341 (19)	0.0211 (19)	0.0535 (19)
C13	0.108 (3)	0.134 (3)	0.083 (2)	0.048 (2)	0.010 (2)	0.060 (2)
C14	0.0760 (19)	0.084 (2)	0.0749 (19)	0.0317 (16)	0.0091 (16)	0.0260 (16)
C15	0.0719 (17)	0.0702 (17)	0.0687 (17)	0.0327 (15)	0.0147 (14)	0.0295 (14)
C16	0.108 (2)	0.0462 (16)	0.097 (2)	0.0126 (15)	−0.0073 (17)	0.0308 (15)
C17A	0.155 (6)	0.062 (5)	0.118 (5)	0.040 (4)	0.010 (4)	0.050 (4)
C5B	0.071 (11)	0.066 (9)	0.081 (14)	0.023 (8)	−0.005 (7)	0.001 (8)
C6B	0.073 (9)	0.074 (9)	0.098 (12)	0.025 (6)	0.004 (7)	0.006 (7)
C7B	0.060 (13)	0.027 (10)	0.083 (18)	−0.002 (9)	0.000 (11)	−0.019 (10)
C17B	0.151 (12)	0.052 (7)	0.076 (8)	0.055 (8)	−0.032 (7)	0.002 (5)

Geometric parameters (Å, º) top

S1—C8	1.733 (3)	C16—C17A	1.436 (8)
S1—C9	1.711 (3)	C16—C17B	1.537 (14)
O1—C1	1.320 (3)	C4—H4A	0.9700
O1—C16	1.460 (3)	C4—H4B	0.9700
O2—C1	1.219 (3)	C5A—H5A	0.9700
O3—C10	1.207 (4)	C5A—H5B	0.9700
N1—C9	1.386 (3)	C5B—H5D	0.9700
N1—C10	1.349 (3)	C5B—H5C	0.9700
N2—C13	1.319 (6)	C6A—H6B	0.9700
N2—C14	1.315 (4)	C6A—H6A	0.9700
N1—H1	0.8600	C6B—H6D	0.9700
C1—C2	1.464 (4)	C6B—H6C	0.9700
C2—C3	1.444 (3)	C7A—H7B	0.9700
C2—C9	1.374 (4)	C7A—H7A	0.9700
C3—C4	1.506 (3)	C7B—H7D	0.9700
C3—C8	1.347 (4)	C7B—H7C	0.9700
C4—C5B	1.53 (2)	C12—H12	0.9300
C4—C5A	1.542 (11)	C13—H13	0.9300
C5A—C6A	1.500 (13)	C14—H14	0.9300
C5B—C6B	1.52 (3)	C15—H15	0.9300
C6A—C7A	1.538 (14)	C16—H16A	0.9700
C6B—C7B	1.54 (3)	C16—H16B	0.9700
C7A—C8	1.489 (12)	C17A—H17C	0.9600
C7B—C8	1.54 (2)	C17A—H17A	0.9600
C10—C11	1.498 (3)	C17A—H17B	0.9600
C11—C12	1.380 (4)	C17B—H17D	0.9600
C11—C15	1.367 (4)	C17B—H17E	0.9600
C12—C13	1.388 (5)	C17B—H17F	0.9600
C14—C15	1.376 (4)

C8—S1—C9	90.88 (13)	H5A—C5A—H5B	108.00
C1—O1—C16	116.6 (2)	C4—C5B—H5C	109.00
C9—N1—C10	126.8 (2)	C4—C5B—H5D	109.00
C13—N2—C14	115.6 (3)	C6B—C5B—H5C	109.00
C10—N1—H1	117.00	C6B—C5B—H5D	109.00
C9—N1—H1	117.00	H5C—C5B—H5D	108.00
O1—C1—C2	113.0 (2)	H6A—C6A—H6B	108.00
O2—C1—C2	124.7 (2)	C5A—C6A—H6A	110.00
O1—C1—O2	122.3 (2)	C5A—C6A—H6B	110.00
C3—C2—C9	111.7 (2)	C7A—C6A—H6A	110.00
C1—C2—C3	128.5 (2)	C7A—C6A—H6B	110.00
C1—C2—C9	119.8 (2)	C7B—C6B—H6C	110.00
C4—C3—C8	121.2 (2)	C7B—C6B—H6D	110.00
C2—C3—C8	111.9 (2)	C5B—C6B—H6D	110.00
C2—C3—C4	126.9 (2)	C5B—C6B—H6C	110.00
C3—C4—C5B	110.8 (10)	H6C—C6B—H6D	108.00
C3—C4—C5A	112.2 (4)	C6A—C7A—H7A	110.00
C4—C5A—C6A	111.4 (7)	C6A—C7A—H7B	110.00
C4—C5B—C6B	111.8 (14)	H7A—C7A—H7B	108.00
C5A—C6A—C7A	110.2 (8)	C8—C7A—H7B	110.00
C5B—C6B—C7B	107.5 (18)	C8—C7A—H7A	110.00
C6A—C7A—C8	108.7 (8)	C6B—C7B—H7C	110.00
C6B—C7B—C8	107.5 (13)	C8—C7B—H7D	110.00
C3—C8—C7B	125.6 (8)	C8—C7B—H7C	110.00
C3—C8—C7A	126.1 (5)	C6B—C7B—H7D	110.00
S1—C8—C3	112.96 (19)	H7C—C7B—H7D	109.00
S1—C8—C7A	121.0 (5)	C11—C12—H12	121.00
S1—C8—C7B	121.3 (8)	C13—C12—H12	121.00
S1—C9—N1	123.36 (19)	C12—C13—H13	118.00
S1—C9—C2	112.64 (19)	N2—C13—H13	118.00
N1—C9—C2	124.0 (2)	C15—C14—H14	118.00
N1—C10—C11	115.4 (2)	N2—C14—H14	118.00
O3—C10—C11	122.7 (2)	C11—C15—H15	120.00
O3—C10—N1	121.8 (2)	C14—C15—H15	120.00
C10—C11—C15	124.5 (2)	O1—C16—H16A	111.00
C10—C11—C12	118.4 (3)	O1—C16—H16B	111.00
C12—C11—C15	117.1 (2)	C17A—C16—H16A	111.00
C11—C12—C13	118.4 (3)	C17A—C16—H16B	111.00
N2—C13—C12	124.8 (3)	H16A—C16—H16B	109.00
N2—C14—C15	124.4 (3)	C17B—C16—H16A	89.00
C11—C15—C14	119.7 (3)	C17B—C16—H16B	126.00
O1—C16—C17B	108.9 (7)	C16—C17A—H17A	109.00
O1—C16—C17A	105.7 (4)	C16—C17A—H17B	109.00
C3—C4—H4A	109.00	C16—C17A—H17C	109.00
C3—C4—H4B	109.00	H17A—C17A—H17B	109.00
C5A—C4—H4A	109.00	H17A—C17A—H17C	109.00
C5A—C4—H4B	109.00	H17B—C17A—H17C	110.00
H4A—C4—H4B	108.00	C16—C17B—H17D	110.00
C5B—C4—H4A	128.00	C16—C17B—H17E	110.00
C5B—C4—H4B	89.00	C16—C17B—H17F	110.00
C4—C5A—H5A	109.00	H17D—C17B—H17E	109.00
C4—C5A—H5B	109.00	H17D—C17B—H17F	109.00
C6A—C5A—H5A	109.00	H17E—C17B—H17F	109.00
C6A—C5A—H5B	109.00

C9—S1—C8—C3	0.1 (2)	C3—C2—C9—S1	−0.2 (3)
C9—S1—C8—C7A	178.7 (6)	C3—C2—C9—N1	179.9 (2)
C8—S1—C9—N1	−180.0 (2)	C2—C3—C4—C5A	169.0 (5)
C8—S1—C9—C2	0.1 (2)	C8—C3—C4—C5A	−10.4 (6)
C16—O1—C1—O2	0.6 (4)	C2—C3—C8—S1	−0.2 (3)
C16—O1—C1—C2	−178.1 (2)	C2—C3—C8—C7A	−178.7 (6)
C1—O1—C16—C17A	165.1 (4)	C4—C3—C8—S1	179.3 (2)
C10—N1—C9—S1	−5.8 (4)	C4—C3—C8—C7A	0.8 (7)
C10—N1—C9—C2	174.1 (2)	C3—C4—C5A—C6A	41.5 (9)
C9—N1—C10—O3	3.3 (4)	C4—C5A—C6A—C7A	−63.6 (10)
C9—N1—C10—C11	−175.2 (2)	C5A—C6A—C7A—C8	51.1 (10)
C14—N2—C13—C12	−0.6 (6)	C6A—C7A—C8—S1	160.6 (5)
C13—N2—C14—C15	0.6 (5)	C6A—C7A—C8—C3	−21.0 (10)
O1—C1—C2—C3	−1.7 (4)	O3—C10—C11—C12	−6.1 (4)
O1—C1—C2—C9	177.4 (2)	O3—C10—C11—C15	175.4 (3)
O2—C1—C2—C3	179.6 (3)	N1—C10—C11—C12	172.3 (3)
O2—C1—C2—C9	−1.3 (4)	N1—C10—C11—C15	−6.2 (4)
C1—C2—C3—C4	−0.1 (4)	C10—C11—C12—C13	−177.6 (3)
C1—C2—C3—C8	179.4 (3)	C15—C11—C12—C13	1.0 (5)
C9—C2—C3—C4	−179.3 (2)	C10—C11—C15—C14	177.5 (3)
C9—C2—C3—C8	0.2 (3)	C12—C11—C15—C14	−1.0 (4)
C1—C2—C9—S1	−179.41 (19)	C11—C12—C13—N2	−0.3 (6)
C1—C2—C9—N1	0.6 (4)	N2—C14—C15—C11	0.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.99	2.650 (3)	132
C7A—H7A···O3ⁱ	0.97	2.56	3.323 (12)	136

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₃S
M_r	330.39
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.5604 (6), 9.3481 (7), 11.7443 (10)
α, β, γ (°)	105.121 (3), 99.748 (2), 110.806 (3)
V (Å³)	811.59 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.18 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD
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	12176, 2914, 1842
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.00
No. of reflections	2914
No. of parameters	243
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

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	1.99	2.650 (3)	132
C7A—H7A···O3ⁱ	0.97	2.56	3.323 (12)	136

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

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

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Mukhtar, A., Tahir, M. N., Khan, M. A. & Khan, M. N. (2010a). Acta Cryst. E66, o2652. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mukhtar, A., Tahir, M. N., Khan, M. A. & Khan, M. N. (2010b). Acta Cryst. E66, o3171. Web of Science CSD 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2041

https://doi.org/10.1107/S1600536812025251

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate