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electronic reprintActa Crystallographica Section E
Structure ReportsOnline
ISSN 1600-5368
Editors: W.T.A. Harrison, J. Simpson andM. Weil
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
This open-access article is distributed under the terms of the Creative Commons Attribution Licencehttp://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, andreproduction in any medium, provided the original authors and source are cited.
Acta Crystallographica Section E
Structure ReportsOnlineEditors: W. Clegg and D. G. Watson
journals.iucr.org
International Union of Crystallography * Chester
ISSN 1600-5368
Volume 61
Part 11
November 2005
Inorganic compounds
Metal-organic compounds
Organic compounds
Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popu-lar open-access structural journal. It provides a simple and easily accessible publicationmechanism for the growing number of inorganic, metal-organic and organic crystal struc-ture determinations. The electronic submission, validation, refereeing and publicationfacilities of the journal ensure very rapid and high-quality publication, whilst key indica-tors and validation reports provide measures of structural reliability. In 2007, the journalpublished over 5000 structures. The average publication time is less than one month.
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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: [email protected]
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
Acta Crystallographica Section E
Structure ReportsOnline
ISSN 1600-5368
electronic reprint