2-Chloro­benzohydrazide

Shakeel Ahmad; Abdul Jabbar; Muhammad Tahir Hussain; M Nawaz Tahir

doi:10.1107/S1600536812012640

. 2012 Mar 31;68(Pt 4):o1254. doi: 10.1107/S1600536812012640

2-Chlorobenzohydrazide

Shakeel Ahmad ^a, Abdul Jabbar ^a, Muhammad Tahir Hussain ^b, M Nawaz Tahir ^c,^*

PMCID: PMC3344182 PMID: 22606185

Abstract

The asymmetric unit of the the title compound, C₇H₇ClN₂O, contains two molecules in which the chlorophenyl and the formic hydrazide units are almost planar (r.m.s. deviations of 0.0081 and 0.0100 Å, respectively, in one molecule and 0.0069 and 0.0150 Å in the other) and are oriented with respect to each other at dihedral angles of 56.8 (2) and 56.9 (2)°. In the crystal, the molecules are consolidated in the form of polymeric chains extending along [010]. R ₃ ³(10) ring motifs exist due to N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For a related structure, see: Zareef et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the synthetic method, see: Moise et al. (2009 ▶).

Experimental

Crystal data

C₇H₇ClN₂O
M _r = 170.60
Monoclinic,
a = 25.7589 (16) Å
b = 4.9618 (3) Å
c = 12.9205 (8) Å
β = 103.648 (3)°
V = 1604.75 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.34 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.979, T _max = 0.988
11488 measured reflections
3091 independent reflections
2089 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.217
S = 1.08
3091 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012640/ez2284sup1.cif

e-68-o1254-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012640/ez2284Isup2.hkl

e-68-o1254-Isup2.hkl^{(148.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012640/ez2284Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.05	2.825 (5)	149
N2—H2A⋯N2ⁱⁱ	0.89 (6)	2.27 (6)	3.151 (7)	172 (5)
N3—H3A⋯O2ⁱⁱⁱ	0.86	2.10	2.812 (5)	140
N4—H4B⋯N4^iv	0.80 (6)	2.40 (6)	3.155 (6)	158 (5)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as a precursor for the preparation of various substituted triazole derivatives.

We have reported the crystal structures of N-2-bromobenzoylhydrazide (Zareef et al., 2006), which is related to (I).

In (I), two molecules are present in the asymmetric unit, which differ slightly from each other geometrically. In one molecule, the chlorophenyl group A (C1–C6/Cl1) and the formic hydrazide moiety B (O1/C7/N1/N2) are planar with r. m. s. deviations of 0.0081Å and 0.0100 Å, respectively. The dihedral angle between A/B is 56.8 (2)°. In second molecule, the chlorophenyl group C (C8–C13/Cl2) and the formic hydrazide moiety D (O2/C14/N3/N4) are also planar with r. m. s. deviation of 0.0069Å and 0.0150 Å, respectively and the dihedral angle between C/D is 56.89 (20)°. Each molecule is connected to symmetry related neighbors through classical intermolecular H–bonding of the N—H···O or N—H···N type (Table 1, Fig. 2) with R₃³(10) ring motifs (Bernstein et al., 1995) to generate one-dimensional polymeric chains along the [0 1 0] direction.

Experimental

2-Chlorobenzoic acid (3.44 g, 22 mmol) was converted to methyl 2-chlorobenzoate by refluxing in methanol (20 ml) in the presence of a catalytic amount of sulfuric acid. This ester was converted into the title compound, 2-chlorobenzoylhydrazide, by refluxing with hydrazine hydrate (80 %, 10 ml) in dry methanol using the literature procedure (Moise et al., 2009). M.p. 379-380K.