4-Hy­droxy-3-meth­oxy­benzaldehyde–nicotinamide (1/1)

Fiona N-F How; M S Amalina; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536811045648

. 2011 Nov 5;67(Pt 12):o3168. doi: 10.1107/S1600536811045648

4-Hydroxy-3-methoxybenzaldehyde–nicotinamide (1/1)

Fiona N-F How ^a, M S Amalina ^a, Hamid Khaledi ^b,^*, Hapipah Mohd Ali ^b

PMCID: PMC3238839 PMID: 22199692

Abstract

In the title compound, C₆H₆N₂O·C₈H₈O₃, an equimolar co-crystal of nicotinamide and vanillin, the aromatic ring and the amide fragment of the nicotinamide molecule make a dihedral angle of 32.6 (2)°. The vanillin molecule is almost planar, with an r.m.s. deviation for all non-H atoms of 0.0094 Å. The vaniline and nicotinamide aromatic rings are nearly coplanar, the dihedral angle between them being 3.20 (9)°. In the crystal, the two components are linked through N—H⋯O and O—H⋯N hydrogen bonds into chains along the a axis. The chains are connected via C—H⋯O interactions, forming a three-dimensional polymeric structure.

Related literature

For the crystal structure of nicotinamide, see: Miwa et al. (1999 ▶); Li et al. (2011 ▶). For the structure of vanillin, see: Velavan et al. (1995 ▶).

Experimental

Crystal data

C₆H₆N₂O·C₈H₈O₃
M _r = 274.27
Triclinic,
a = 4.8979 (1) Å
b = 8.5440 (2) Å
c = 15.4713 (4) Å
α = 98.108 (1)°
β = 92.810 (2)°
γ = 94.784 (2)°
V = 637.52 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.22 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.996
3432 measured reflections
2243 independent reflections
1862 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.112
S = 1.05
2243 reflections
191 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.28 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045648/pv2471sup1.cif

e-67-o3168-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045648/pv2471Isup2.hkl

e-67-o3168-Isup2.hkl^{(110.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811045648/pv2471Isup3.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—H1A⋯O4ⁱ	0.87 (2)	2.05 (2)	2.900 (2)	167 (2)
N1—H1B⋯O2ⁱⁱ	0.87 (2)	2.42 (2)	3.085 (2)	134 (2)
N1—H1B⋯O3ⁱⁱ	0.87 (2)	2.20 (2)	3.019 (2)	156 (2)
O2—H2⋯N2ⁱⁱⁱ	0.85 (2)	1.80 (2)	2.634 (2)	164 (2)
C8—H8A⋯O1^iv	0.98	2.59	3.381 (3)	137
C8—H8C⋯O2ⁱ	0.98	2.55	3.337 (2)	138
C13—H13⋯O1^v	0.95	2.49	3.185 (3)	130

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

Acknowledgments

IIUM is acknowledged for funding this study (Endowment fund A No. EDWA10–150–0697).

supplementary crystallographic information

Comment

The crystal structures of nicotinamide (Miwa et al.,1999; Li et al., 2011) and 4-hydroxy-3-methoxybenzaldehyde, vanillin, (Velavan et al.,1995) have been previously reported. The title compound is an equimolar cocrystal of nicotinamide and vanillin (Fig. 1). The nicotinamide aromatic ring and the plane of the amide fragment, N1—C9—O4, are twisted with respect to each other, making a dihedral angle of 32.6 (2)°. The vanillin molecule is essentially planar, the highest deviation from the best plane passing through all non-H atoms being 0.0156 (13) Å for O3 atom. In the crystal, the molecules of nicotinamide and vanillin are linked through N—H···O and O—H···N hydrogen bonds into infinite chains along the a axis (Fig. 2). The chains are connected via C—H···O interactions (Table 1 and Fig. 2) to form a three-dimensional polymeric structure.

Experimental

A mixture of vanillin (1.52 g, 0.1 mol) and nicotinamide (1.22 g, 0.1 mol) in ethanol (30 ml) was heated for 1 hr. The solvent was then evaporated partially and the solution was left at room temperature. The colorless crystals of the title compound were obtained in a day.