(2E)-2-(4-Hy­droxy-3-meth­oxy­benzyl­idene)hydrazinecarboxamide

M Nawaz Tahir; Akbar Ali; M Naveed Umar; Ishtiaq Hussain; Hazoor Ahmad Shad

doi:10.1107/S1600536812025299

. 2012 Jun 13;68(Pt 7):o2071. doi: 10.1107/S1600536812025299

(2E)-2-(4-Hydroxy-3-methoxybenzylidene)hydrazinecarboxamide

M Nawaz Tahir ^a,^*, Akbar Ali ^b, M Naveed Umar ^b, Ishtiaq Hussain ^c, Hazoor Ahmad Shad ^d

PMCID: PMC3393335 PMID: 22807892

Abstract

In the title compound, C₉H₁₁N₃O₃, two molecules are present in the asymmetric unit in which the 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide units are almost planar [with r.m.s. deviations 0.0212 and 0.0066 Å, respectively, in one molecule and 0.0346 and 0.0095 Å, respectively, in the other] and are oriented at dihedral angles of 9.7 (3) and 16.6 (3)°. In both molecules, two S(5) ring motifs are present due to N—H⋯N and O—H⋯O hydrogen bonds. In the crystal, the molecules are dimerized with each other due to pairs of N—H⋯O hydrogen bonds, forming an R ₂ ²(8) ring motif. O—H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For a related structure, see: Tahir et al. (2012 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₉H₁₁N₃O₃
M _r = 209.21
Orthorhombic,
a = 13.9945 (14) Å
b = 5.0440 (4) Å
c = 27.286 (2) Å
V = 1926.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.957, T _max = 0.966
8297 measured reflections
1931 independent reflections
1046 reflections with I > 2σ(I)
R _int = 0.081

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.113
S = 0.98
1931 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 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 ▶) 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/S1600536812025299/bq2364sup1.cif

e-68-o2071-sup1.cif^{(27.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025299/bq2364Isup2.hkl

e-68-o2071-Isup2.hkl^{(93.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025299/bq2364Isup3.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⋯O1	0.82	2.17	2.627 (6)	115
O2—H2A⋯O5ⁱ	0.82	2.34	3.108 (7)	156
N2—H2B⋯O6ⁱⁱ	0.86	2.11	2.923 (7)	158
N3—H3A⋯O6ⁱⁱⁱ	0.86	2.16	2.987 (7)	162
N3—H3B⋯N1	0.86	2.31	2.674 (8)	106
O5—H5A⋯O4	0.82	2.18	2.632 (6)	115
N5—H5B⋯O3^iv	0.86	2.08	2.909 (7)	161
N6—H6A⋯O3^v	0.86	2.13	2.965 (7)	164
N6—H6B⋯N4	0.86	2.32	2.677 (7)	105

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as a derivative. Recently we have reported the crystal structure of (2E)-2-(3,4-dimethoxybenzylidene)hydrazinecarboxamide (Tahir et al., 2012) which is related to the title compound.

In (I), two molecules are present in the asymmetric unit, which differ slightly from each other geometrically. In one molecule, the parts of 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide A (C1—C8/O1/O2) and B (N1/N2/C9/N3/O3), are almost planar with r.m.s. deviations of 0.0212 Å and 0.0066 Å, respectively. The dihedral angle between A/B is 16.57 (26)°. In the second molecule, the similar groups C (C10—C17/O4/O5) and D (N4/N5/C18/N6/O6) are also planar with r.m.s. deviations of 0.0346 Å and 0.0095 Å, respectively, and the dihedral angle between C/D is 9.74 (28)°. In both molecules two S(5) ring motifs (Bernstein et al., 1995) are present due to H–bonding of N—H···N and O—H···O types (Table 1, Fig. 1). The molecules are dimerized with each other due to N—H···O type of H-bondings and form R₂²(8) ring motifs (Table 1, Fig. 2). The molecules are stabilized in the form of three-dimensional polymeric network.

Experimental

Equimolar quantities of 4-hydroxy-3-methoxybenzaldehyde and hydrazinecarboxamide were refluxed in methanol along with few drops of acetic acid as catalyst for 45 min resulting in light orange solution. The solution was kept at room temperature which afforded light orange needles after few days.