2,4-Bis(4-fluoro­phen­yl)-2,3-dihydro-1H-1,5-benzodiazepine

Baktır, Z.; Akkurt, M.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811015455

Volume 67
Part 5
Pages o1262-o1263
May 2011

Received 15 April 2011
Accepted 24 April 2011
Online 29 April 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R = 0.061
wR = 0.151
Data-to-parameter ratio = 14.6
Details

2,4-Bis(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine

Zeliha Baktir,^a Mehmet Akkurt,^a ^* S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₂₁H₁₆F₂N₂, the seven-membered 1,4-diazepine ring of the benzodiazepine ring system adopts a distorted-boat conformation. The benzene ring of this system makes dihedral angles of 18.6 (2) and 78.8 (2)° with those of two fluorophenyl substituents. In the crystal, inversion dimers linked by two weak C-HF hydrogen bonds generate R₂²(20) ring motifs. There are also weak N-H [pi] and C-H [pi] interactions.

Related literature

For related structures, see: An et al. (2007); Bibila Mayaya Bisseyou et al. (2010); Harrison et al. (2005); Peeters et al. (1997). For puckering parameters, see: Cremer & Pople (1975). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₁₆F₂N₂
M_r = 334.36
Monoclinic, P 2₁ /n
a = 12.9151 (4) Å
b = 6.0438 (3) Å
c = 21.2851 (7) Å
= 92.147 (3)°
V = 1660.27 (11) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: refined from F (XABS2; Parkin et al., 1995) T_min = 0.981, T_max = 0.981
3413 measured reflections
3413 independent reflections
1226 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.151
S = 1.04
3413 reflections
233 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the benzene rings of the two fluorophenyl substituents (C10-C15 and C16-C21, respectively).

D-HA	D-H	HA	DA	D-HA
C5-H5F1ⁱ	0.93	2.54	3.469 (6)	175
N1-H1NCg2ⁱ	0.86 (3)	2.82 (5)	3.601 (4)	151 (4)
C2-H2Cg1ⁱⁱ	0.93	2.89	3.640 (5)	138
C11-H11Cg2	0.93	2.79	3.494 (5)	134
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5848 ).

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10-2949, and for support of the data collection at Atatürk University, Turkey. SS and BN thank Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
An, L.-T., Ding, F.-Q., Zou, J.-P. & Lu, X.-H. (2007). Acta Cryst. E63, o3272-o3273.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bibila Mayaya Bisseyou, Y., Adjou, A., Yapo, Y. M., Bany, G. E. & Kakou-Yao, R. C. A. (2010). Acta Cryst. E66, o87-o88.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Harrison, W. T. A., Yathirajan, H. S., Anilkumar, H. G., Sarojini, B. K., Narayana, B. & Lobo, K. G. (2005). Acta Cryst. E61, o3810-o3812.
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.
Peeters, O. M., Blaton, N. M. & de Ranter, C. J. (1997). Acta Cryst. C53, 95-97.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds