4-(4-Bromo­phenyl­hydrazono)-1-(5-bromo­pyrimidin-2-yl)-3-methyl-2-pyrazolin-5-one

Subramanyam, M.; Lingappa, B.; Thiruvalluvar, A.; Butcher, R.J.; Kalluraya, B.

doi:10.1107/S1600536807067943

Volume 64
Part 2
Page o362
February 2008

Received 16 November 2007
Accepted 20 December 2007
Online 4 January 2008

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.008 Å
R = 0.083
wR = 0.139
Data-to-parameter ratio = 23.0
Details

4-(4-Bromophenylhydrazono)-1-(5-bromopyrimidin-2-yl)-3-methyl-2-pyrazolin-5-one

M. Subramanyam,^a B. Lingappa,^b A. Thiruvalluvar,^a ^* R. J. Butcher ^c and Balakrishna Kalluraya ^b

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India,^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: athiru@vsnl.net

The asymmetric unit of the title compound, C₁₄H₁₀Br₂N₆O, contains two crystallographically independent molecules. The pyrazole ring of one molecule makes dihedral angles of 22.0 (3) and 3.5 (3)° with the pyrimidine and benzene rings, respectively; the corresponding values in the other molecule are 9.2 (3) and 2.1 (3)°, respectively. The molecules are linked by N-HO, C-HN and C-HBr hydrogen bonds.

Related literature

For related literature, see: Baraldi et al. (1996, 2003); Kalluraya & Rahiman (1997); Kalluraya et al. (2001); Lingappa et al. (2006, 2007). For related crystal structures, see: Thiruvalluvar, Subramanyam, Kalluraya et al. (2007a,b); Thiruvalluvar, Subramanyam, Lingappa et al. (2007).

Experimental

Crystal data

C₁₄H₁₀Br₂N₆O
M_r = 438.08
Triclinic, $[P \overline 1]$
a = 9.1647 (3) Å
b = 12.2833 (5) Å
c = 14.0288 (5) Å
= 86.532 (3)°
= 84.218 (3)°
= 78.747 (3)°
V = 1539.67 (10) Å³
Z = 4
Mo K radiation
= 5.28 mm^-1
T = 200 (2) K
0.44 × 0.39 × 0.28 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.205, T_max = 0.320 (expected range = 0.146-0.228)
24958 measured reflections
9542 independent reflections
6336 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.082
wR(F²) = 0.139
S = 1.25
9542 reflections
415 parameters
H-atom parameters constrained
_max = 0.83 e Å^-3
_min = -0.64 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N6A-H6AO5A	0.88	2.14	2.821 (6)	134
N6B-H6BO5B	0.88	2.10	2.782 (6)	134
C13A-H13AN12Bⁱ	0.95	2.61	3.193 (7)	120
C15A-H15ABr4ⁱⁱ	0.95	2.92	3.761 (6)	148
C15B-H15BBr2ⁱⁱ	0.95	2.87	3.746 (6)	153
C31A-H31ABr3ⁱ	0.98	2.88	3.858 (6)	173
C31B-H31DBr1ⁱ	0.98	2.92	3.862 (6)	160
C45A-H45AN16Bⁱⁱ	0.95	2.62	3.539 (7)	162
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2116 ).

Acknowledgements

RJB acknowledges the NSF-MRI program for funding to purchase the X-ray CCD diffractometer. AT thanks the UGC, India, for the award of a Minor Research Project [file No. MRP-2355/06(UGC-SERO), link No. 2355, 10/01/2007].

References

Baraldi, P. G., Cacciari, B. & Spalluto, G. (1996). J. Med. Chem. 39, 1164-1169.
Baraldi, P. G., Fruttarolo, F., Tabrizi, M. A., Preti, D., Romagnoli, H., El-Kashef, H., Moorman, A., Varani, K., Gessi, S., Merighi, S. & Borea, P. A. (2003). J. Med. Chem. 46, 1229-1233.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kalluraya, B. & Rahiman, A. M. (1997). Pol. J. Chem. 1049, 71-75.
Kalluraya, B., Rahiman, A. M. & Banji, D. (2001). Arch. Pharm. Med. Chem. 263, 334-341.
Lingappa, B., Kalluraya, B. & Satheesha Rai, N. (2006). Indian J. Org. Chem. 2, 5-6.
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Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Thiruvalluvar, A., Subramanyam, M., Kalluraya, B. & Lingappa, B. (2007a). Acta Cryst. E63, o2911.
Thiruvalluvar, A., Subramanyam, M., Kalluraya, B. & Lingappa, B. (2007b). Acta Cryst. E63, o3362.
Thiruvalluvar, A., Subramanyam, M., Lingappa, B. & Kalluraya, B. (2007). Acta Cryst. E63, o3425.

organic compounds