3-Chloro­benzohydrazide

Uzma Ashiq; Rifat Ara Jamal; Muhammad Nadeem Arshad; Islam Ullah Khan

doi:10.1107/S1600536810029508

. 2010 Jul 31;66(Pt 8):o2169. doi: 10.1107/S1600536810029508

3-Chlorobenzohydrazide

Uzma Ashiq ^a,^*, Rifat Ara Jamal ^a, Muhammad Nadeem Arshad ^b, Islam Ullah Khan ^b

PMCID: PMC3007237 PMID: 21588450

Abstract

In the title compound, C₇H₇ClN₂O, the hydrazide group is inclined at a dihedral angle of 32.30 (11)° with respect to the benzene ring. The amino H atoms form intermolecular N—H⋯O hydrogen bonds with the O atoms of two adjacent molecules, resulting in 10-membered rings of graph-set motif R ₂ ²(10). The imino H atom is also involved in an intermolecular hydrogen bond with an amino N atom of a symmetry-related molecule, resulting in a zigzag chain along the b axis. The structure is further consolidated by an intramolecular N—H⋯O interaction, which results in a five-membered ring.

Related literature

For the biological activity of hydrazides, see: Ashiq, Ara et al. (2008 ▶); Ara et al. (2007 ▶); Maqsood et al. (2006 ▶); For related structures, see: Ashiq, Jamal et al. (2008 ▶); Jamal et al. (2008 ▶, 2009 ▶); Kallel et al. (1992 ▶); Ratajczak et al. (2001 ▶); Saraogi et al. (2002 ▶). For graph-set notation of hydrogen-bond motifs, see: (Bernstein et al. 1995 ▶).

Experimental

Crystal data

C₇H₇ClN₂O
M _r = 170.60
Monoclinic,
a = 16.2005 (15) Å
b = 3.8165 (4) Å
c = 12.7646 (13) Å
β = 108.030 (5)°
V = 750.47 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 296 K
0.43 × 0.21 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.832, T _max = 0.928
8144 measured reflections
1881 independent reflections
1101 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.121
S = 1.01
1880 reflections
109 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029508/pv2308sup1.cif

e-66-o2169-sup1.cif^{(14.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029508/pv2308Isup2.hkl

e-66-o2169-Isup2.hkl^{(90.6KB, hkl)}

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
N2—H2N⋯O1	0.90 (3)	2.45 (3)	2.766 (3)	101 (2)
N1—H1N⋯N2ⁱ	0.87 (3)	2.11 (3)	2.955 (3)	162 (2)
N2—H3N⋯O1ⁱⁱ	0.86 (3)	2.24 (3)	3.091 (3)	171 (2)
N2—H2N⋯O1ⁱⁱⁱ	0.90 (3)	2.25 (3)	2.935 (3)	133 (2)

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

Acknowledgments

The authors thank the Higher Education Commission Pakistan for providing the diffractometer at GCU, Lahore, and BANA International for the data collection.

supplementary crystallographic information

Comment

Hydrazides are known to have different biological activities (Ashiq, Ara et al., 2008; Ara et al., 2007). In order to study the biological activity of 3-chlorobenzohydrazide, we undertook the synthesis of the title compound and report its crystal structure in this paper. The title compound was found to be antifungal (Maqsood et al., 2006). The structures of benzhydrazide (Kallel et al., 1992), and its p-chloro (Saraogi et al., 2002), m-methoxy (Jamal et al., 2009), m-nitro (Ratajczak et al. 2001), p-bromo (Ashiq, Jamal et al., 2008) and p-iodo (Jamal et al., 2008) analogues have been reported.

The bond lengths and bond angles in the title compound (Fig. 1) are comparable with the corresponding distances and angles reported in its analogues quoted above. The hydrazide moiety, C7/O1/N1/N2, is oriented at a dihedral angle of 32.30 (11)° with respect to the plane of benzene ring C1–C6. The H atoms bonded to N2 form intermolecular hydrogen bonds of the type N–H···O with O atoms of two adjacent molecules, resulting in 10-membered rings which may be assigned to R₂²(10) motif in graph set notation (Bernstein et al., 1995). The H-atom bonded to N1 is also involved in an intermolecular hydrogen bond with N2, linking the molecules into a zigzag chain along the b axis (Tab. 1 and Fig. 2). The structure is further stabilized by an intramolecular interaction, N2–H2···O1, resulting in a five membered ring in S(5) motif (Bernstein et al., 1995).

Experimental

All reagent-grade chemicals were obtained from Aldrich and Sigma Chemical companies and were used without further purification. To a solution of ethyl-3-chlorobenzoate (3.69 g, 20 mmol) in 75 ml ethanol, hydrazine hydrate (5.0 ml, 100 mmol) was added. The mixture was refluxed for 5 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford the title compound (yield 75%). The crystals of the title compound suitable for crystallographic study were grown from a solution of methanol by slow evaporation at room temperature.