N′-[(E)-(1-Methyl-1H-pyrrol-2-yl)methyl­idene]benzohydrazide

Hussain, A.; Shafiq, Z.; Tahir, M.N.; Yaqub, M.

doi:10.1107/S1600536810025390

Volume 66
Part 8
Page o1888
August 2010

Received 26 June 2010
Accepted 28 June 2010
Online 3 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.139
Data-to-parameter ratio = 18.9
Details

N'-[(E)-(1-Methyl-1H-pyrrol-2-yl)methylidene]benzohydrazide

Abid Hussain,^a Zahid Shafiq,^a M. Nawaz Tahir ^b ^* and Muhammad Yaqub ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C₁₃H₁₃N₃O, the phenyl and pyrrole rings are inclined at 47.45 (8)°. In the crystal, intermolecular N-HO and C-HO hydrogen bonds form R₂¹(6) ring motifs. Molecules connected through these hydrogen bonds are arranged into polymeric chains extending along the c axis.

Related literature

For related structures, see: Shafiq et al. (2009a,b). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₁₃N₃O
M_r = 227.26
Monoclinic, P 2₁ /c
a = 11.1170 (8) Å
b = 11.6329 (9) Å
c = 9.6735 (6) Å
= 110.241 (3)°
V = 1173.75 (15) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.28 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.942, T_max = 0.952
11164 measured reflections
2930 independent reflections
1770 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.139
S = 1.02
2930 reflections
155 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.11	2.910 (2)	155
C8-H8O1ⁱ	0.93	2.38	3.209 (2)	148
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2289 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009a). Acta Cryst. E65, o2501.
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009b). Acta Cryst. E65, o2898.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds