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Volume 69 
Part 4 
Pages o482-o483  
April 2013  

Received 25 February 2013
Accepted 26 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.179
Data-to-parameter ratio = 17.4
Details
Open access

N'-[3-Cyano-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromen-2-yl]-N,N-dimethylmethanimidamide

aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,bPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,cDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,dApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and fChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C24H20FN3O2, despite the 4H-pyran ring having a flattened half-chair conformation [the methine C atom lies 0.257 (3) Å above the plane of the remaining atoms with an r.m.s. deviation of 0.0295 Å], the 14 non-H atoms of the 4H-benzo[h]chromene residue are approximately coplanar (r.m.s. deviation = 0.081 Å). The benzene ring is nearly perpendicular to this plane [dihedral angle = 76.18 (10)°], but the planar (r.m.s. deviation = 0.033 Å) dimethylmethanimidamide substituent is coplanar [dihedral angle = 1.96 (12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C-H...N interactions, and these are connected into supramolecular layers in the ab plane by C-H...[pi] and [pi]-[pi] [intercentroid (central C6 ring)...(outer C6 ring)i distance = 3.8564 (14) Å] interactions.

Related literature

For background to synthetic aspects of benzochromene derivatives, see: El-Agrody et al. (2011[El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.]); 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.]). For biological interest in these derivatives, see: 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.]); Vukovic et al. (2010[Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Food Chem. 120, 1011-1018.]); Abd-El-Aziz et al. (2007[Abd-El-Aziz, A. S., Mohamed, H. M., Mohammed, S., Zahid, S., Ata, A., Bedair, A. H., El-Agrody, A. M. & Harvey, P. D. (2007). J. Heterocycl. Chem. 44, 1287-1301.]). For a closely related structure, 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
  • C24H20FN3O2

  • Mr = 401.43

  • Triclinic, [P \overline 1]

  • a = 8.8438 (8) Å

  • b = 11.0887 (12) Å

  • c = 11.8001 (13) Å

  • [alpha] = 66.054 (10)°

  • [beta] = 83.684 (8)°

  • [gamma] = 75.946 (9)°

  • V = 1025.85 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 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 = 0.982, Tmax = 1.000

  • 9814 measured reflections

  • 4745 independent reflections

  • 2729 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.179

  • S = 1.04

  • 4745 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C18-C23, C2-C7 and C1,C2,C7-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C23-H23...N3i 0.93 2.62 3.542 (3) 171
C5-H5...Cg1ii 0.93 2.79 3.670 (3) 159
C15-H15B...Cg2iii 0.96 2.93 3.732 (3) 142
C16-H16C...Cg3iii 0.96 2.91 3.589 (3) 129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z; (iii) x+1, y, z.

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: HG5296 ).


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

Abd-El-Aziz, A. S., Mohamed, H. M., Mohammed, S., Zahid, S., Ata, A., Bedair, A. H., El-Agrody, A. M. & Harvey, P. D. (2007). J. Heterocycl. Chem. 44, 1287-1301.  [ChemPort]
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]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.  [ChemPort]
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]
Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Food Chem. 120, 1011-1018.  [ISI] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o482-o483   [ doi:10.1107/S1600536813005503 ]

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