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Volume 69 
Part 4 
Pages o480-o481  
April 2013  

Received 25 February 2013
Accepted 25 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.150
Data-to-parameter ratio = 17.1
Details
Open access

2-Amino-4-(4-bromophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile

aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,bChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt,cPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,dDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,eApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and gChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromobenzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supramolecular layers parallel to (101) are sustained by amine-cyano N-H...N and amine-methoxy N-H...O hydrogen bonds. The layers stack with interactions of the type (bromobenzene)C-H...[pi](outer-C6 ring of the fused-ring system) connecting them.

Related literature

For background to biologically active molecules having the 4H-chromene or 4H-benzochromene residue, see: Sabry et al. (2011[Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.]); Amin et al. (2010[Amin, K. M., Kamel, M. M., Anwar, M. M., Khedr, M. & Syam, Y. M. (2010). Eur. J. Med. Chem. 45, 2117-2131.]); Kidwai et al. (2010[Kidwai, M., Poddar, R., Bhardwaj, S., Singh, S. & Mehta Luthra, P. (2010). Eur. J. Med. Chem. 45, 5031-5038.]); Singh et al. (2010[Singh, O. M., Devi, N. S., Thokchom, D. S. & Sharma, G. J. (2010). Eur. J. Med. Chem. 45, 2250-2257.]), For the structure of the fluoro derivative, see: Al-Dies et al. (2012[Al-Dies, A.-A. M., Amr, A.-G. E., El-Agrody, A. M., Chia, T. S. & Fun, H.-K. (2012). Acta Cryst. E68, o1934-o1935.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15BrN2O2

  • Mr = 407.26

  • Monoclinic, P 21 /c

  • a = 6.0823 (7) Å

  • b = 16.6918 (18) Å

  • c = 17.7700 (16) Å

  • [beta] = 93.646 (9)°

  • V = 1800.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.30 mm-1

  • T = 295 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.694, Tmax = 1.000

  • 8976 measured reflections

  • 4144 independent reflections

  • 2250 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.150

  • S = 1.03

  • 4144 reflections

  • 243 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.78 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.88 (1) 2.22 (2) 3.059 (5) 159 (4)
N1-H2...O2ii 0.87 (3) 2.56 (5) 3.324 (4) 147 (4)
C18-H18...Cg1iii 0.93 2.87 3.528 (4) 129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7048 ).


Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group project No. RGP-VPP-099. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Dies, A.-A. M., Amr, A.-G. E., El-Agrody, A. M., Chia, T. S. & Fun, H.-K. (2012). Acta Cryst. E68, o1934-o1935.  [CSD] [CrossRef] [details]
Amin, K. M., Kamel, M. M., Anwar, M. M., Khedr, M. & Syam, Y. M. (2010). Eur. J. Med. Chem. 45, 2117-2131.  [ISI] [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kidwai, M., Poddar, R., Bhardwaj, S., Singh, S. & Mehta Luthra, P. (2010). Eur. J. Med. Chem. 45, 5031-5038.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, O. M., Devi, N. S., Thokchom, D. S. & Sharma, G. J. (2010). Eur. J. Med. Chem. 45, 2250-2257.  [ISI] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o480-o481   [ doi:10.1107/S1600536813005461 ]

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