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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 [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.161
Data-to-parameter ratio = 15.5
Details
Open access

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

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-H...N 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[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011a). Acta Cryst. E67, o2254.],b[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2355.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18N2OS

  • Mr = 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[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.858, Tmax = 1.000

  • 28490 measured reflections

  • 7066 independent reflections

  • 5288 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...N1 0.82 (3) 1.84 (3) 2.578 (2) 150 (3)
O2-H2O...N3 0.82 (3) 1.84 (3) 2.582 (2) 151 (3)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


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.  [CSD] [CrossRef] [details]
Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2355.  [CSD] [CrossRef] [details]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o193  [ doi:10.1107/S160053681300007X ]

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