Crystal structure of 2-amino-N-(2-fluoro­phen­yl)-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carboxamide

K Chandra Kumar; V Umesh; T K Madhura; B M Rajesh; Chandra

doi:10.1107/S2056989015018022

. 2015 Oct 3;71(Pt 11):o807–o808. doi: 10.1107/S2056989015018022

Crystal structure of 2-amino-N-(2-fluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

K Chandra Kumar ^a, V Umesh ^b, T K Madhura ^c, B M Rajesh ^a, Chandra ^d,^*

PMCID: PMC4645083 PMID: 26594537

Abstract

In the title compound, C₁₅H₁₅FN₂OS, the dihedral angle between the planes of the benzothiophene ring system and the fluorobenzene ring is 3.74 (14)°. The six-membered ring of the benzothiophene moiety adopts a half-chair conformation. The molecular conformation is consolidated by intramolecular N—H⋯F and N—H⋯O hydrogen bonds. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(6) [001] chains.

Keywords: crystal structure, benzothiophene derivative, biological properties, hydrogen bonding

Related literature

For background to thiophene derivatives, see: Bonini et al. (2005 ▸); Brault et al. (2005 ▸); Isloor et al. (2010 ▸). For intermolecular interactions involving F atoms, see: Choudhury et al. (2004 ▸). graphic file with name e-71-0o807-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₅FN₂OS
M _r = 290.36
Monoclinic
a = 11.213 (13) Å
b = 14.231 (17) Å
c = 9.582 (15) Å
β = 116.76 (3)°
V = 1365 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
5264 measured reflections
2577 independent reflections
2363 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.081
S = 1.84
2577 reflections
182 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▸)
Absolute structure parameter: 0.06 (7)

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: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015018022/hb7493sup1.cif

e-71-0o807-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018022/hb7493Isup2.hkl

e-71-0o807-Isup2.hkl^{(126.6KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015018022/hb7493Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015018022/hb7493fig1.tif

Perspective diagram of the molecule with 50% probability displacement ellipsoids.

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015018022/hb7493fig2.tif

Packing diagram of the molecule viewed down the ’a′ axis.

CCDC reference: 1045467

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N8H9AF7	0.86	2.26	2.643(5)	107
N16H15CO10	0.86	2.16	2.733(5)	124
N16H15DO10ⁱ	0.86	2.25	2.986(6)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the University of Mysore and HKBK College of Engineering for support.

supplementary crystallographic information

S1. Comment

Thiophene nucleus has been established as a potential entity in the largely growing chemical world of heterocyclic compounds possessing promising pharmacological characteristics such as anti-HIV PR inhibitors (Bonini et al., 2005) and anti-breast cancer (Brault et al., 2005) activities. Particularly, benzothiophene derivative shows significant antimicrobial and anti- inflammatory activities (Isloora et al., 2010). In addition structures containing fluorine atoms plays a major role in intermolecular interactions (Choudhury et al., 2004). The title compound was prepared and characterized by single-crystal X-ray diffraction studies.

In the molecular structure of the title compound (Fig. 1), the dihedral angle between the flurobenzene (C1–C2–C3–C4–C5–C6) and benzothiophene (C11–C12–C13–S14–C15–C17–C18–C19–C20) ring is 3.74 (14)°. The benzothiophene moiety adopts a half chair conformation conformation with puckering parameter Q = 0.475 (3) Å and φ = 215.4 (5)°, and the maximum deviation found on the puckered atom at C18 is 0.372 (4) Å. The carboximidamide unit is in anti-periplanar conformation with respect to the benzothiophene moiety, as indicated by the torsion angle value of 161.9 (3)° (N8–C9–C11–C15). The crystal structure features intermolecular N—H···O hydrogen bonds. The packing diagram of the molecule viewed down the a axis as shown in Fig. 2.

S2. Experimental

Cyclohexanone (1 equiv.), 2-cyano-N-(2-fluorophenyl) acetamide (1.1 equiv.), elemental sulfur (1.2 equiv.), diethylamine (0.8 equiv.) was taken in ethanol and mixed thoroughly in a microwave tube. The tube was sealed and irradiated at 325 K for 15 min. After cooling ethyl acetate was added to the reaction mixture and solid residue was removed by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain yellow block shaped crystals.