7-(4-Bromo­phen­yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra­zolo[1,5-c]pyrimidine

Jotani, M.M.; Shah, R.D.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536810004368

Volume 66
Part 3
Page o574
March 2010

Received 2 February 2010
Accepted 3 February 2010
Online 10 February 2010

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.090
Data-to-parameter ratio = 22.2
Details

7-(4-Bromophenyl)-9-phenyl-7H-pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine

Mukesh M. Jotani,^a Rina D. Shah,^b Jerry P. Jasinski ^c ^* and Ray J. Butcher ^d

^aDepartment of Physics, Bhavan's Sheth R.A. College of Science, Ahmedabad, Gujarat, 380 001, India,^bDepartment of Chemistry, M.G. Science Institute, Navrangpura, Navrangpura, Ahmedabad, Gujarat, 380 009, India,^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C₁₈H₁₁BrN₆, the phenyl ring is almost coplanar [dihedral angle 7.2 (1)°] with the planar (r.m.s. deviation 0.039 Å) tricyclic ring system while the 4-bromophenyl ring makes a dihedral angle of 33.98 (6)° with the ring system. Weak intermolecular C-HN and C-HBr hydrogen-bonding interactions and [pi] - [pi] stacking [centroid-centroid distances = 3.7971 (17) and 3.5599 (16) Å] stabilize the crystal packing. A comparison of the structure to a MOPAC PM3 geometry optimization calculation in vacuo supports these observations.

Related literature

For anticancer relationships, see: Hiedo & Yasuo (1960, 1961). For the synthesis of derivative compounds, see: Dave & Shukla (1997); Dave & Shah (1998). For graph-set motifs, see: Bernstein et al. (1995). For MOPAC PM3 calculations, see: Schmidt & Polik (2007).

Experimental

Crystal data

C₁₈H₁₁BrN₆
M_r = 391.24
Monoclinic, P 2₁ /c
a = 12.0173 (5) Å
b = 17.4007 (7) Å
c = 7.4201 (4) Å
= 91.004 (4)°
V = 1551.37 (12) Å³
Z = 4
Mo K radiation
= 2.66 mm^-1
T = 200 K
0.47 × 0.39 × 0.22 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.494, T_max = 1.000
13458 measured reflections
5032 independent reflections
2606 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.090
S = 1.14
5032 reflections
227 parameters
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.71 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8N4ⁱ	0.95	2.54	3.421 (3)	154
C4-H4N5ⁱ	0.95	2.60	3.532 (3)	166
C5-H5Brⁱⁱ	0.95	2.87	3.667 (3)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5188 ).

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Dave, C. G. & Shah, R. D. (1998). J. Heterocycl. Chem. 35, 1295-1300.
Dave, C. G. & Shukla, M. C. (1997). J. Heterocycl. Chem. 34, 1805-1808.
Hiedo, K. & Yasuo, M. (1960). Japan Patent 17,236.
Hiedo, K. & Yasuo, M. (1961). Chem. Abstr. 55, 17664.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds