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Volume 69 
Part 4 
Pages o478-o479  
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 = 0.052
wR = 0.145
Data-to-parameter ratio = 15.9
Details
Open access

3-Amino-1-(4-fluorophenyl)-7-methoxy-1H-benzo[f]chromene-2-carbonitrile

aDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,cChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,dChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt,ePharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,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, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C5 plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluorobenzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supramolecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {...HNC3N}2 and eight-membered {...HNCO}2 synthons. These are connected into a three-dimensional architecture by [pi]-[pi] [intercentroid distance for centrosymmetrically related fluorobenzene rings = 3.5181 (10) Å] and C-H...[pi] interactions.

Related literature

For a related structure and background to 4H-chromene derivatives, see: El-Agrody et al. (2013[El-Agrody, A. M., Al-Omar, M. A., Amr, A. E.-G. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o476-o477.]). 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.]);

[Scheme 1]

Experimental

Crystal data
  • C21H15FN2O2

  • Mr = 346.35

  • Triclinic, [P \overline 1]

  • a = 8.7798 (9) Å

  • b = 9.6329 (6) Å

  • c = 10.9130 (11) Å

  • [alpha] = 77.074 (7)°

  • [beta] = 68.414 (10)°

  • [gamma] = 87.083 (7)°

  • V = 835.99 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.30 × 0.30 × 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 = 0.821, Tmax = 1.000

  • 7587 measured reflections

  • 3868 independent reflections

  • 2569 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.145

  • S = 1.02

  • 3868 reflections

  • 244 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15-CC20 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.89 (2) 2.34 (3) 3.189 (2) 160 (2)
N1-H2...O1ii 0.87 (2) 2.36 (3) 3.219 (2) 169 (2)
C19-H19...Cg1iii 0.93 2.90 3.831 (2) 174
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+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: HB7049 ).


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.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Agrody, A. M., Al-Omar, M. A., Amr, A. E.-G. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o476-o477.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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, o478-o479   [ doi:10.1107/S1600536813005473 ]

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