2-(2,3-Dimethyl­anilino)benzohydrazide

Hoong-Kun Fun; Tze Shyang Chia; Tilal Elsaman; Mohamed I Attia; Hatem A Abdel-Aziz

doi:10.1107/S1600536812032576

. 2012 Jul 25;68(Pt 8):o2527–o2528. doi: 10.1107/S1600536812032576

2-(2,3-Dimethylanilino)benzohydrazide

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Tilal Elsaman ^b, Mohamed I Attia ^b, Hatem A Abdel-Aziz ^b

PMCID: PMC3414975 PMID: 22904962

Abstract

In the title compound, C₁₅H₁₇N₃O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif in the molecule, and a short intramolecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π interactions.

Related literature

For the biological activity of fenamates, see: Boschelli et al. (1990 ▶); Reddy et al. (2010 ▶); Aboul-Fadl et al. (2011 ▶). For the synthesis, see: Reddy et al. (2010 ▶); Aboul-Fadl et al. (2011 ▶). For a related structure, see: Bhat et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₇N₃O
M _r = 255.32
Triclinic,
a = 6.9092 (8) Å
b = 6.9609 (7) Å
c = 14.9458 (15) Å
α = 81.562 (2)°
β = 81.328 (2)°
γ = 66.269 (2)°
V = 647.56 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.28 × 0.18 × 0.13 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.977, T _max = 0.989
8491 measured reflections
2218 independent reflections
1826 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.108
S = 1.05
2218 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032576/hb6900sup1.cif

e-68-o2527-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032576/hb6900Isup2.hkl

e-68-o2527-Isup2.hkl^{(109KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032576/hb6900Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N3ⁱ	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1⋯O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A⋯Cg1ⁱⁱ	0.93	2.58	3.303 (2)	135
C14—H14C⋯Cg1ⁱⁱⁱ	0.96	2.77	3.535 (2)	137

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for funding and facilities.

supplementary crystallographic information

Comment

Mefenamic acid (MFA), N-(2,3-xylyl)anthranilic acid and meclofenamic acid (MCFA) are derivatives of fenamates. They are non-steroidal anti-inflammatory drugs (NSAIDs) used as potent analgesic and anti-inflammatory agents in the treatment of osteoarthritis and rheumatoid arthritis (Boschelli et al., 1990; Reddy et al., 2010; Aboul-Fadl et al., 2011). In view of the importance of the hydrazide of fenamic acid as an active synthon in the synthesis of compounds with biological interests (Reddy et al., 2010; Bhat et al., 2012), we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The C1–C6 benzene ring makes a dihedral angle of 58.05 (9)° with the C7–C12 benzene ring. The non-H atoms of hydrazide group (O1/N2/N3/C13) lie nearly on a plane [r.m.s. deviation = 0.0006 Å] and are nearly coplanar with the attached C7–C12 benzene ring as indicated by the dihedral angle of 8.02 (9)°. An intramolecular N1—H1N1···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) in the molecule. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in a related structure (Bhat et al., 2012).

In the crystal (Fig. 2), the molecules are linked by pairs of intermolecular N2—H1N2···N3 hydrogen bond into inversion dimers. The crystal packing is further stabilized by C—H···π interactions (Table 1), involving Cg1 which is the centroid of C1–C6 ring. A short intramolecular contact [H1N2···H9A = 1.88 Å] is also observed.

Experimental

The title compound was prepared by the reaction of the methyl ester of fenamic acid with hydrazine hydrate or with the direct reaction of fenamic acid with hydrazine hydrate under microwave irritation (Reddy et al., 2010; Aboul-Fadl et al., 2011). Brown blocks were grown from the slow evaporation of a methanol solution.