2-[(2-Hy­droxy­naphthalen-1-yl)methyl­idene­amino]-5,6,7,8-tetra­hydro-4H-cyclo­hepta­[b]thio­phene-3-carbonitrile

Asiri, A.M.; Arshad, M.N.; Sobahi, T.R.; Mustafa, G.

doi:10.1107/S160053681300007X

Volume 69
Part 2
Page o193
February 2013

Received 27 December 2012
Accepted 2 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.161
Data-to-parameter ratio = 15.5
Details

2-[(2-Hydroxynaphthalen-1-yl)methylideneamino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile

Abdullah M. Asiri,^a,^b ^* Muhammad Nadeem Arshad,^a,^b Tariq R. Sobahi ^a and Ghulam Mustafa ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,^bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^cDepartment of Chemistry, University of Gujrat, Gujrat, Pakistan
Correspondence e-mail: aasiri2@kau.edu.sa, ghulam.mustafa@uog.edu.pk

Two independent molecules, A and B, comprise the asymmetric unit of the title compound, C₂₁H₁₈N₂OS, with the difference in the angle of orientation between the naphthalene ring system and the mean plane of the cycloheptyl ring [16.13 (1) in A and 11.48 (5)° in B], being evident. The cycloheptyl ring adopts a distorted chair conformation in each molecule with r.m.s. deviations of 0.2345 (4) (A) and 0.2302 (4) Å (B). Intramolecular O-HN hydrogen bonding generates planar six-membered S(6) loops with r.m.s. deviations of 0.0099 (1) (A) and 0.0286 (1) Å (B).

Related literature

For the synthesis and related structures, see: Asiri et al. (2011a,b). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₁₈N₂OS
M_r = 346.43
Orthorhombic, P b c a
a = 13.5472 (2) Å
b = 14.4747 (4) Å
c = 35.7902 (6) Å
V = 7018.2 (2) Å³
Z = 16
Cu K radiation
= 1.71 mm^-1
T = 296 K
0.37 × 0.21 × 0.14 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.858, T_max = 1.000
28490 measured reflections
7066 independent reflections
5288 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.161
S = 1.02
7066 reflections
457 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.52 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1ON1	0.82 (3)	1.84 (3)	2.578 (2)	150 (3)
O2-H2ON3	0.82 (3)	1.84 (3)	2.582 (2)	151 (3)

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5186 ).

Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via Research Group Track grant No. 3-102/428.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011a). Acta Cryst. E67, o2254.
Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2355.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds