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Volume 69 
Part 4 
Pages o476-o477  
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) = 0.003 Å
R = 0.049
wR = 0.138
Data-to-parameter ratio = 16.0
Details
Open access

3-Amino-1-(4-fluorophenyl)-8-methoxy-1H-benzo[f]chromene-2-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

The title compound, C21H15FN2O2, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluorobenzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine-cyano N-H...N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C-H...N(cyano), C-H...[pi] and [pi]-[pi] [intercentroid distance = 3.6671 (10) Å] interactions.

Related literature

For background and various applications of benzo- and naphthopyran- derivatives, see: Bonsignore et al. (1993[Bonsignore, L., Loy, G., Secci, D. & Calignano, A. (1993). Eur. J. Med. Chem. 28, 517-520.]); Hafez et al. (1987[Hafez, E. A. A., Elnagdi, M. H., Elagamey, A. G. A. & El-Taweel, F. M. A. A. (1987). Heterocycles, 26, 903-907.]). For background to the chemistry and biological activity of 4H-pyran 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 related structures, see: Wang et al. (2008[Wang, X.-S., Yang, G.-S. & Zhao, G. (2008). Tetrahedron Asymmetry, 19, 709-714.]); Shekhar et al. (2012[Shekhar, A. C., Kumar, A. R., Sathaiah, G., Raju, K., Rao, P. S., Sridhar, M., Narsaiah, B., Srinivas, P. V. S. S. & Sridhar, B. (2012). Helv. Chim. Acta, 95, 502-508.]); Amr et al. (2013[Amr, A. E.-G. E., El-Agrody, A. M., Al-Omar, M. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o478-o479.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15FN2O2

  • Mr = 346.35

  • Triclinic, [P \overline 1]

  • a = 8.9672 (7) Å

  • b = 10.4365 (8) Å

  • c = 10.9058 (8) Å

  • [alpha] = 103.063 (7)°

  • [beta] = 106.859 (7)°

  • [gamma] = 111.399 (8)°

  • V = 844.01 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 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 = 0.722, Tmax = 1.000

  • 7109 measured reflections

  • 3902 independent reflections

  • 2716 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.138

  • S = 1.05

  • 3902 reflections

  • 244 parameters

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C4,C9,C10 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.89 (2) 2.16 (2) 3.043 (2) 170.0 (18)
C19-H19...N2ii 0.93 2.51 3.259 (3) 138
C11-H11...Cg1iii 0.98 2.90 3.7084 (17) 141
C14-H14C...Cg1iv 0.96 2.92 3.772 (3) 148
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+2, -z+1.

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: HB7047 ).


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.
Amr, A. E.-G. E., El-Agrody, A. M., Al-Omar, M. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o478-o479.  [CrossRef] [details]
Bonsignore, L., Loy, G., Secci, D. & Calignano, A. (1993). Eur. J. Med. Chem. 28, 517-520.  [CrossRef] [ChemPort] [ISI]
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]
Hafez, E. A. A., Elnagdi, M. H., Elagamey, A. G. A. & El-Taweel, F. M. A. A. (1987). Heterocycles, 26, 903-907.  [ChemPort]
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]
Shekhar, A. C., Kumar, A. R., Sathaiah, G., Raju, K., Rao, P. S., Sridhar, M., Narsaiah, B., Srinivas, P. V. S. S. & Sridhar, B. (2012). Helv. Chim. Acta, 95, 502-508.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, X.-S., Yang, G.-S. & Zhao, G. (2008). Tetrahedron Asymmetry, 19, 709-714.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o476-o477   [ doi:10.1107/S160053681300545X ]

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