{2-[(2-Bromo-5-meth­oxy­benzyl­idene)amino]-4,5,6,7-tetra­hydro­benzo[b]thiophen-3-yl}(phen­yl)methanone

Manpreet Kaur; Jerry P Jasinski; Thammarse S Yamuna; H S Yathirajan; K Byrappa

doi:10.1107/S1600536814008290

. 2014 Apr 18;70(Pt 5):o581–o582. doi: 10.1107/S1600536814008290

{2-[(2-Bromo-5-methoxybenzylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}(phenyl)methanone

Manpreet Kaur ^a, Jerry P Jasinski ^b,^*, Thammarse S Yamuna ^a, H S Yathirajan ^a, K Byrappa ^c

PMCID: PMC4011278 PMID: 24860382

Abstract

In the title compound, C₂₃H₂₀BrNO₂S, disorder was modeled for the outer two C atoms of the cyclohexene ring over two sets of sites with an occupancy ratio of 0.580 (11):0.420 (11). Both rings have a half-chair conformation. The dihedral angles between the mean plane of the thiophene ring and the benzene and phenyl rings are 9.2 (2) and 66.1 (2)°, respectively. The benzene and phenyl rings are inclined to each other by 74.8 (8)°. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For applications of 2-aminothiophene derivatives, see: Sabnis et al. (1999 ▶); Puterová et al. (2010 ▶). For the biological and industrial importance of Schiff bases, see: Desai et al. (2001 ▶); Karia & Parsania (1999 ▶); Samadhiya & Halve (2001 ▶); Singh & Dash (1988 ▶); Aydogan et al. (2001 ▶); Taggi et al. (2002 ▶). For a related structure, see: Kubicki et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₂₀BrNO₂S
M _r = 454.37
Monoclinic,
a = 8.84813 (17) Å
b = 12.5563 (2) Å
c = 18.4384 (4) Å
β = 102.363 (2)°
V = 2001.00 (7) Å³
Z = 4
Cu Kα radiation
μ = 3.92 mm⁻¹
T = 173 K
0.26 × 0.22 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.725, T _max = 1.000
12404 measured reflections
3853 independent reflections
3440 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.087
S = 1.05
3853 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008290/su2721sup1.cif

e-70-0o581-sup1.cif^{(31.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008290/su2721Isup2.hkl

e-70-0o581-Isup2.hkl^{(211.4KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814008290/su2721Isup3.cml

CCDC reference: 997010

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.95	2.58	3.294 (3)	132

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Symmetry code: (i) Inline graphic .

Acknowledgments

MK is grateful to the CPEPA–UGC for the award of a Junior Research Fellowship and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

1. Comment

2-Aminothiophene derivatives have been used in a number of applications in pesticides, dyes and pharmaceuticals (Sabnis et al. 1999; Puterová et al. 2010). Schiff base compounds show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al., 2001; Karia & Parsania, 1999; Samadhiya & Halve, 2001; Singh & Dash, 1988) and have been used as starting materials in the synthesis of compounds of industrial (Aydogan et al., 2001) and biological interest such as β-lactams (Taggi et al., 2002). In continuation of our work on the Schiff base derivatives of 2-aminothiophenes (Kubicki et al., 2012), we report herein on the crystal structure of the title compound.

In the title compound, Fig. 1, disorder was modeled for atoms C5 and C6 of the cyclohexene ring over two sites (A and B) with an occupancy ratio of 0.580 (11):0.420 (11). Both rings have half-chair conformations with puckering parameters (Cremer & Pople, 1975) Q,θ, and φ being = 0.520 (6) Å, 49.9 (4) ° and 154.8 (6) °, respectively, for ring A and being = 0.527 (8) Å, 130.1 (5) ° and 322.0 (7) °, respectively, for ring B. The dihedral angles between the mean plane of the thiophene ring and the benzene and phenyl rings are 9.2 (2) ° and 66.1 (2) °, respectively. The benzene and phenyl rings are twisted with respect to each other by 74.8 (8)°. Bond lengths are in normal ranges (Allen et al., 1987).

In the crystal, molecules are linked by pairs of C-H···O hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

2. Experimental

To a solution of (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)- phenyl-methanone (200 mg, 0.79 mmol) in 10 ml of methanol an equimolar amount of 2-bromo-5-methoxybenzaldehyde (170 mg, 0.79 mmol) was added with constant stirring. The mixture was then refluxed for 6 hours and a yellow precipitate was obtained. The reaction completion was confirmed by thin layer chromatography. The precipitate was filtered and dried at room temperature overnight. Slow evaporation of a solution in CH₂Cl₂ gave yellow block-like crystals of the title compound.