![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
Ethyl 2-(pyridine-4-carboxamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
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
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.
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S1600536812025251/hb6838sup1.cif
contains datablocks global, I. DOI: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
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%.
In the cyclohexane ring three methelene groups and terminal C-atom of ethyl ester are disordered over two set of sites with occupancy ratio of 0.691 (14):0.309 (14).
The H-atoms were positioned geometrically (N—H = 0.86, C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for other H-atoms.
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).
For related structures, see: Mukhtar et al. (2010a,b).
Data collection: APEX2 (Bruker, 2009); cell
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).C17H18N2O3S | Z = 2 |
Mr = 330.39 | F(000) = 384 |
Triclinic, P1 | Dx = 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 |
Bruker Kappa APEXII CCD diffractometer | 2914 independent reflections |
Radiation source: fine-focus sealed tube | 1842 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.10 pixels mm-1 | θmax = 25.3°, θmin = 2.5° |
ω scans | h = −10→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −11→11 |
Tmin = 0.953, Tmax = 0.958 | l = −14→14 |
12176 measured reflections |
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(Fo2) + (0.049P)2 + 0.1304P] where P = (Fo2 + 2Fc2)/3 |
2914 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.15 e Å−3 |
10 restraints | Δρmin = −0.18 e Å−3 |
C17H18N2O3S | γ = 110.806 (3)° |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 2914 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1842 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.958 | Rint = 0.039 |
12176 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 10 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.15 e Å−3 |
2914 reflections | Δρmin = −0.18 e Å−3 |
243 parameters |
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. |
x | y | z | Uiso*/Ueq | 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) |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.953, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12176, 2914, 1842 |
Rint | 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 |
Δρmax, Δρmin (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).
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.
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).