2-[(4-Chloro­benzyl­idene)amino]-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carbonitrile

Abdullah M Asiri; Salman A Khan; M Nawaz Tahir

doi:10.1107/S1600536811030704

. 2011 Aug 6;67(Pt 9):o2254. doi: 10.1107/S1600536811030704

2-[(4-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile

Abdullah M Asiri ^a,^b, Salman A Khan ^b, M Nawaz Tahir ^c,^*

PMCID: PMC3200595 PMID: 22058913

Abstract

In the title compound, C₁₆H₁₃ClN₂S, the dihedral angle between the 4-chlorobenzaldehyde moiety and the heterocyclic five-membered ring is 7.21 (17)°. In the crystal, molecules are linked by weak C—H⋯π interactions, generating [100] chains.

Related literature

For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₃ClN₂S
M _r = 300.79
Orthorhombic,
a = 4.7815 (3) Å
b = 16.5670 (13) Å
c = 18.1658 (14) Å
V = 1439.01 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.931, T _max = 0.951
11075 measured reflections
2607 independent reflections
1821 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.099
S = 1.02
2607 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 1053 Friedel pairs
Flack parameter: 0.03 (10)

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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030704/hb6331sup1.cif

e-67-o2254-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030704/hb6331Isup2.hkl

e-67-o2254-Isup2.hkl^{(125.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030704/hb6331Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg is the centroid of the C8–C11/S1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.97	2.99	3.841 (6)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for providing the research facilities and for the financial support of this work via grant No. (3–045/430).

supplementary crystallographic information

Comment

We have reported the crystal structure of 2-[(benzo[1,3]dioxol-5-ylmethylene)-amino]-4,5,6,7-tetrahydro-benzo[b]thiophene -3-carbonitrile (Asiri et al., 2011) which is related to the title compound, (I), Fig. 1.

In (I), the group A (C1–C7/CL1) of 4-chlorobenzaldehyde and the five membered ring B (C8—C11/S1) of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3- carbonitrile group are almost planar with r. m. s. deviation of 0.0150 and 0.0110 Å, respectively. The dihedral angle between A/B is 7.21 (17)°. A C—H···π interaction (Table 1) occurs in the crystal.

Experimental

A mixture of 4-chloro benzaldehyde (0.46 g, 2.4 mmol) and 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-carbonitrile (0.32 g, 3.3 mmol) in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture (8:2) to give yellow needles of the title compound (I). Yield: 82%, m.p. 504–505 K.