3,5-Bis(4-fluoro­phen­yl)-1-(4-nitro­phen­yl)-4,5-dihydro-1H-pyrazole

Samshuddin, S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S160053681204370X

Volume 68
Part 11
Pages o3216-o3217
November 2012

Received 17 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.067
wR = 0.221
Data-to-parameter ratio = 17.0
Details

3,5-Bis(4-fluorophenyl)-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole

Seranthimata Samshuddin,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₂₁H₁₅F₂N₃O₂, a pyrazole derivative bearing three aromatic substituents, the central five-membered heterocyclic ring makes dihedral angles of 1.77 (14), 3.68 (13) and 72.15 (14)° with the three benzene rings. In the crystal, C-HO and C-HF interactions connect the molecules into double layers parallel to the bc plane.

Related literature

For general information about the pharmacological properties and medical applications of pyrazole derivatives, see: Kumar et al. (2009); Sarojini et al. (2010); Samshuddin et al. (2012). For the crystal structures of other pyrazole derivatives, see: Baktir et al. (2011); Jasinski et al. (2012). For the puckering analysis of cyclic motifs, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₁₅F₂N₃O₂
M_r = 379.36
Monoclinic, P 2₁ /c
a = 13.2884 (13) Å
b = 12.7364 (10) Å
c = 11.4656 (9) Å
= 115.324 (3)°
V = 1754.0 (3) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 200 K
0.57 × 0.33 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.692, T_max = 0.971
15973 measured reflections
4301 independent reflections
3066 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.221
S = 1.06
4301 reflections
253 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O2ⁱ	0.95	2.41	3.305 (3)	157
C16-H16F2ⁱⁱ	0.95	2.55	3.427 (3)	154
C26-H26F1ⁱⁱⁱ	0.95	2.56	3.494 (3)	169
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5210 ).

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292-o1293.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jasinski, J. P., Golen, J. A., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2012). Crystals, 2, 1108-1115.
Kumar, S., Bawa, S., Drabu, S., Kumar, R. & Gupta, H. (2009). Recent Pat. Anti-infect. Drug Discov. 4, 154-163.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2012). Med. Chem. Res. 21, 2012-2022.
Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214-224.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds