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N ′-[(1E)-1-(4-Chlorophenyl)ethylidene]formohydrazide

Zahid Shafiq, Muhammad Yaqub, M. Nawaz Tahir, Mian Hasnain Nawazand M. Saeed Iqbal

Acta Cryst. (2009). E65, o2494

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Acta Cryst. (2009). E65, o2494 Shafiq et al. · C9H9ClN2O

N000-[(1E)-1-(4-Chlorophenyl)ethylidene]-formohydrazide

Zahid Shafiq,a Muhammad Yaqub,a M. Nawaz Tahir,b

Mian Hasnain Nawaza and M. Saeed Iqbalc*

aDepartment of Chemistry, Bahauddin Zakariya University, Multan-60800, Pakistan,bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, andcDepartment of Chemistry, Government College University, Lahore, Pakistan

Correspondence e-mail: dmntahir_uos@yahoo.com

Received 5 September 2009; accepted 14 September 2009

Key indicators: single-crystal X-ray study; T = 296 K; mean �(C–C) = 0.003 A;

R factor = 0.050; wR factor = 0.150; data-to-parameter ratio = 19.4.

The structure of the title compound, C9H9ClN2O, consists of

centrosymmetric dimers due to intermolecular N—H� � �Ohydrogen bonding, forming R2

2(8) ring motifs. The dihedral

angle between the p-chlorophenyl unit and the remaining

heavy-atom group is 6.77 (17)�.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995). For a

related structure, see: Guo (2007).

Experimental

Crystal data

C9H9ClN2OMr = 196.63Monoclinic, P21=ca = 5.9373 (5) Ab = 6.2178 (4) A

c = 25.3495 (18) A� = 93.900 (4)�

V = 933.66 (12) A3

Z = 4Mo K� radiation

� = 0.37 mm�1

T = 296 K0.25 � 0.22 � 0.18 mm

Data collection

Bruker Kappa APEXII CCDdiffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2005)Tmin = 0.914, Tmax = 0.940

9690 measured reflections2311 independent reflections1426 reflections with I > 2�(I)Rint = 0.025

Refinement

R[F 2 > 2�(F 2)] = 0.050wR(F 2) = 0.150S = 1.052311 reflections

119 parametersH-atom parameters constrained��max = 0.26 e A�3

��min = �0.20 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N2—H2A� � �O1i 0.8600 2.0800 2.920 (3) 164.00

Symmetry code: (i) �x;�y;�z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT

(Bruker, 2007); 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.

The authors acknowledge the Higher Education Commis-

sion, Islamabad, Pakistan, and Bana International, Karachi,

Pakistan, for funding the purchase of the diffractometer at

GCU, Lahore, and for technical support, respectively.

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: BQ2157).

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 (2007). 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.Guo, H.-M. (2007). Acta Cryst. E63, o3870.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.

organic compounds

o2494 Shafiq et al. doi:10.1107/S1600536809037143 Acta Cryst. (2009). E65, o2494

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