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Volume 69 
Part 3 
Page o401  
March 2013  

Received 13 February 2013
Accepted 14 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.091
Data-to-parameter ratio = 12.8
Details
Open access

3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fAnalytical Sciences, Manchester Metropolitan University, Manchester M1 5GD, England
Correspondence e-mail: akkurt@erciyes.edu.tr, shaabankamel@yahoo.com

In the title compound, C20H14N2O, the phenyl ring is almost normal to the naphthalene ring system with a dihedral angle of 86.72 (9)°. The 4H-pyran ring fused with the naphthalene ring system has a boat conformation. In the crystal, molecules are linked into a helical supramolecular chain along the b axis via N-H...N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C-H...[pi] interactions.

Related literature

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007[Ellis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1-1196. London: Wiley-VCH.]); Horton et al. (2003[Horton, D. A., Boume, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the graph-set analysis of hydrogen bonding, 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
  • C20H14N2O

  • Mr = 298.33

  • Monoclinic, P 21

  • a = 9.4059 (8) Å

  • b = 6.5009 (5) Å

  • c = 12.4919 (10) Å

  • [beta] = 105.914 (9)°

  • V = 734.57 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 123 K

  • 0.30 × 0.12 × 0.07 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.955, Tmax = 1.000

  • 3674 measured reflections

  • 2780 independent reflections

  • 2477 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.091

  • S = 1.06

  • 2780 reflections

  • 217 parameters

  • 49 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4/C5/C10-C13 and C5-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...N2i 0.90 (3) 2.16 (2) 2.978 (3) 150 (2)
N1-H2N...N2ii 0.87 (3) 2.33 (3) 3.138 (3) 154 (2)
C7-H7...Cg3iii 0.95 2.84 3.561 (2) 133
C12-H12...Cg2iv 0.95 2.68 3.446 (2) 139
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z]; (ii) x, y-1, z; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5198 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Ellis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1-1196. London: Wiley-VCH.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Horton, D. A., Boume, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
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, o401  [ doi:10.1107/S1600536813004376 ]

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