(E)-3-Chloro-N′-hy­droxy­benzene-1-carboximidamide

S Sreenivasa; K E ManojKumar; P A Suchetan; N R Mohan; B S Palakshamurthy

doi:10.1107/S1600536812046612

. 2012 Nov 24;68(Pt 12):o3402. doi: 10.1107/S1600536812046612

(E)-3-Chloro-N′-hydroxybenzene-1-carboximidamide

S Sreenivasa ^a,^*, K E ManojKumar ^a, P A Suchetan ^b, N R Mohan ^a, B S Palakshamurthy ^c

PMCID: PMC3588992 PMID: 23476228

Abstract

The title compound, C₇H₇ClN₂O, crystallizes with two independent molecules in the asymmetric unit. The compound adopts an E configuration across the C=N double bond, as the –OH group and the benzene ring are on opposite sides of the double bond while the H atom of the hydroxy group is directed away from the –NH₂ group. In the crystal, molecules are linked to one another through O—H⋯N and N—H⋯O hydrogen bonds, forming chains along [010].

Related literature

For related syntheses and the biological activity of oxadiazoles, see: Kundu et al. (2012 ▶); Sakamoto et al. (2007 ▶); Tyrkov & Sukhenko (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₇H₇ClN₂O
M _r = 170.60
Triclinic,
a = 5.0018 (17) Å
b = 10.984 (4) Å
c = 14.407 (6) Å
α = 74.000 (12)°
β = 89.952 (12)°
γ = 89.877 (11)°
V = 760.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 298 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.902, T _max = 0.917
14972 measured reflections
2655 independent reflections
2192 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.109
S = 1.05
2655 reflections
218 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(21.4KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046612/jj2159sup1.cif

e-68-o3402-sup1.cif^{(21.4KB, cif)}

Click here for additional data file.^{(130.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046612/jj2159Isup2.hkl

e-68-o3402-Isup2.hkl^{(130.4KB, hkl)}

Click here for additional data file.^{(3.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812046612/jj2159Isup3.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
O2—H2A⋯N4ⁱ	0.82	2.09	2.811 (2)	147
N3—H3B⋯O1ⁱⁱ	0.92 (3)	2.32 (3)	3.006 (2)	131 (2)
O1—H1⋯N2ⁱⁱⁱ	0.82	2.08	2.805 (2)	147
N1—H1B⋯O2^iv	0.87 (3)	2.36 (3)	3.006 (3)	132 (3)

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

Acknowledgments

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement, and Professor T. N. Guru Row and Vijithkumar, S. S. C. U, Indian Institute of Science, Bangalore, for their help with the data collection. They also thank Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support.

supplementary crystallographic information

Comment

Substituted N'-hydroxybenzamidines is a key intermediate obtained during the synthesis of pharmaceutically important 1,2,4-oxadiazole derivatives. 1,2,4-Oxadiazole derivatives are well known for their anti-HIV and anti-microbial activities (Kundu et al., 2012; Sakamoto et al., 2007; Tyrkov et al., 2004). In our studies on these types of compounds, we synthesized the title compound,C₇H₇ClN₂O, (I) and report here its crystal structure.

The title compound, (I), crystallizes with two independent molecules (A & B) in the asymmetric unit (Fig. 1). The compound prefers an E configuration across the C—N double bond, as the OH group and the benzene ring are on opposite sides of the double bond while the hydrogen atom of the hydroxyl group is directed away from the NH₂ group. In the crystal, the independent molecules (A & B) are connected to their respective crystallographically identical molecules through O1—H1···N2 and O2—H2···N4 intermolecular hydrogen bonds, each forming R₂²(6) dimeric pairs (Fig 2). The dimeric pairs are further connected to one another through intermolecular N1-H1N1···O2 and N3-H3N3···O1 hydrogen bonds forming a chain of ring patterns (Bernstein et al., 1995) along [010] (Fig 2).

Experimental

To a solution of 3-chlorobenzonitrile (1 mmol) in ethanol was added triethyl amine (2.5 mmol) and NH₂OH.HCl (3.5 mmol). The reaction mixture was stirred at room temperature for 12hrs. (The reaction was monitored by TLC). The solvent was removed and the crude product was purified by column chromatography using hexane and ethyl acetate as the eluent. Single crystals required for X-ray diffraction measurements were obtained from slow evaporation of the solution of the compound in a mixture of ethanol and dichloromethane (1:4).