4-Hy-droxy-3-meth-oxy-benzaldehyde-nicotinamide (1/1).

In the title compound, C(6)H(6)N(2)O·C(8)H(8)O(3), an equimolar co-crystal of nicotinamide and vanillin, the aromatic ring and the amide fragment of the nicotinamide mol-ecule make a dihedral angle of 32.6 (2)°. The vanillin mol-ecule 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 inter-actions, 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 = 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

Δρmax = 0.66 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811045648/pv2471Isup3.cml

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

C6H6N2O·C8H8O3	Z = 2
Mr = 274.27	F(000) = 288
Triclinic, P1	Dx = 1.429 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8979 (1) Å	Cell parameters from 1226 reflections
b = 8.5440 (2) Å	θ = 2.6–29.7°
c = 15.4713 (4) Å	µ = 0.11 mm−1
α = 98.108 (1)°	T = 100 K
β = 92.810 (2)°	Lath, colorless
γ = 94.784 (2)°	0.22 × 0.14 × 0.04 mm
V = 637.52 (3) Å3

Bruker APEXII CCD diffractometer	2243 independent reflections
Radiation source: fine-focus sealed tube	1862 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.977, Tmax = 0.996	k = −10→10
3432 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.4685P] where P = (Fo2 + 2Fc2)/3
2243 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.66 e Å−3
4 restraints	Δρmin = −0.28 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.3651 (3)	0.83011 (19)	0.61085 (10)	0.0359 (4)
O2	0.8107 (3)	0.63328 (16)	0.23075 (9)	0.0195 (3)
H2	0.949 (4)	0.698 (2)	0.2250 (15)	0.029*
O3	0.4028 (3)	0.44026 (16)	0.25734 (9)	0.0218 (3)
C1	0.3070 (5)	0.7306 (3)	0.54863 (14)	0.0286 (5)
H1	0.1529	0.6570	0.5522	0.034*
C2	0.4516 (4)	0.7113 (2)	0.46701 (13)	0.0210 (4)
C3	0.6726 (4)	0.8148 (2)	0.45164 (13)	0.0221 (5)
H3	0.7380	0.9016	0.4951	0.026*
C4	0.7972 (4)	0.7912 (2)	0.37307 (13)	0.0204 (4)
H4	0.9482	0.8620	0.3629	0.024*
C5	0.7035 (4)	0.6648 (2)	0.30888 (12)	0.0166 (4)
C6	0.4793 (4)	0.5600 (2)	0.32443 (12)	0.0176 (4)
C7	0.3561 (4)	0.5847 (2)	0.40255 (13)	0.0208 (5)
H7	0.2040	0.5146	0.4128	0.025*
C8	0.1709 (4)	0.3323 (2)	0.26827 (14)	0.0217 (5)
H8A	0.2110	0.2765	0.3179	0.033*
H8B	0.1328	0.2551	0.2150	0.033*
H8C	0.0103	0.3917	0.2793	0.033*
O4	0.8254 (3)	0.71964 (19)	−0.04761 (9)	0.0299 (4)
N1	0.3766 (4)	0.6341 (2)	−0.07875 (11)	0.0205 (4)
H1A	0.207 (3)	0.645 (3)	−0.0672 (14)	0.025*
H1B	0.415 (4)	0.586 (2)	−0.1293 (11)	0.025*
N2	0.2385 (3)	0.80224 (19)	0.18395 (10)	0.0170 (4)
C9	0.5840 (4)	0.7129 (2)	−0.02755 (13)	0.0197 (4)
C10	0.5123 (4)	0.7959 (2)	0.05932 (12)	0.0169 (4)
C11	0.6653 (4)	0.9350 (2)	0.09779 (13)	0.0201 (4)
H11	0.8121	0.9801	0.0687	0.024*
C12	0.5998 (4)	1.0066 (2)	0.17913 (13)	0.0220 (5)
H12	0.6997	1.1023	0.2066	0.026*
C13	0.3864 (4)	0.9363 (2)	0.21971 (13)	0.0192 (4)
H13	0.3429	0.9856	0.2757	0.023*
C14	0.3015 (4)	0.7346 (2)	0.10499 (12)	0.0162 (4)
H14	0.1966	0.6397	0.0788	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0440 (10)	0.0363 (9)	0.0266 (9)	0.0056 (8)	0.0038 (7)	0.0006 (7)
O2	0.0182 (8)	0.0217 (7)	0.0174 (7)	−0.0031 (6)	0.0053 (6)	0.0004 (6)
O3	0.0223 (8)	0.0214 (7)	0.0198 (7)	−0.0045 (6)	0.0064 (6)	−0.0016 (6)
C1	0.0356 (13)	0.0308 (12)	0.0189 (10)	0.0104 (10)	−0.0028 (9)	−0.0012 (9)
C2	0.0226 (11)	0.0246 (11)	0.0170 (10)	0.0074 (8)	0.0004 (8)	0.0045 (8)
C3	0.0270 (11)	0.0214 (10)	0.0165 (10)	0.0060 (9)	−0.0036 (8)	−0.0020 (8)
C4	0.0187 (10)	0.0193 (10)	0.0218 (11)	−0.0018 (8)	−0.0001 (8)	0.0014 (8)
C5	0.0157 (10)	0.0209 (10)	0.0145 (9)	0.0054 (8)	0.0026 (8)	0.0043 (8)
C6	0.0193 (10)	0.0176 (10)	0.0157 (10)	0.0033 (8)	0.0002 (8)	0.0007 (8)
C7	0.0193 (11)	0.0242 (11)	0.0199 (10)	0.0020 (8)	0.0046 (8)	0.0055 (8)
C8	0.0185 (11)	0.0198 (10)	0.0259 (11)	−0.0031 (8)	0.0035 (8)	0.0021 (8)
O4	0.0144 (8)	0.0516 (10)	0.0228 (8)	0.0064 (7)	0.0038 (6)	−0.0003 (7)
N1	0.0172 (9)	0.0279 (9)	0.0153 (9)	0.0046 (7)	0.0035 (7)	−0.0030 (7)
N2	0.0171 (9)	0.0194 (8)	0.0148 (8)	0.0031 (7)	0.0012 (6)	0.0027 (6)
C9	0.0178 (11)	0.0255 (11)	0.0168 (10)	0.0055 (8)	0.0018 (8)	0.0042 (8)
C10	0.0144 (10)	0.0210 (10)	0.0156 (10)	0.0038 (8)	−0.0008 (7)	0.0030 (8)
C11	0.0149 (10)	0.0240 (10)	0.0221 (10)	0.0003 (8)	0.0020 (8)	0.0058 (8)
C12	0.0227 (11)	0.0180 (10)	0.0234 (11)	−0.0030 (8)	−0.0011 (8)	−0.0002 (8)
C13	0.0217 (11)	0.0192 (10)	0.0160 (10)	0.0031 (8)	0.0002 (8)	0.0001 (8)
C14	0.0157 (10)	0.0162 (9)	0.0161 (10)	0.0009 (7)	−0.0013 (8)	0.0012 (7)

O1—C1	1.197 (3)	C8—H8B	0.9800
O2—C5	1.343 (2)	C8—H8C	0.9800
O2—H2	0.854 (16)	O4—C9	1.236 (2)
O3—C6	1.365 (2)	N1—C9	1.330 (3)
O3—C8	1.435 (2)	N1—H1A	0.868 (16)
C1—C2	1.474 (3)	N1—H1B	0.869 (16)
C1—H1	0.9500	N2—C13	1.336 (2)
C2—C3	1.391 (3)	N2—C14	1.338 (2)
C2—C7	1.396 (3)	C9—C10	1.500 (3)
C3—C4	1.384 (3)	C10—C14	1.388 (3)
C3—H3	0.9500	C10—C11	1.392 (3)
C4—C5	1.391 (3)	C11—C12	1.384 (3)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.410 (3)	C12—C13	1.384 (3)
C6—C7	1.375 (3)	C12—H12	0.9500
C7—H7	0.9500	C13—H13	0.9500
C8—H8A	0.9800	C14—H14	0.9500
C5—O2—H2	112.6 (16)	O3—C8—H8C	109.5
C6—O3—C8	117.44 (15)	H8A—C8—H8C	109.5
O1—C1—C2	126.2 (2)	H8B—C8—H8C	109.5
O1—C1—H1	116.9	C9—N1—H1A	121.6 (15)
C2—C1—H1	116.9	C9—N1—H1B	117.5 (15)
C3—C2—C7	119.56 (18)	H1A—N1—H1B	120 (2)
C3—C2—C1	122.83 (19)	C13—N2—C14	117.72 (17)
C7—C2—C1	117.59 (19)	O4—C9—N1	123.82 (19)
C4—C3—C2	119.93 (19)	O4—C9—C10	119.84 (18)
C4—C3—H3	120.0	N1—C9—C10	116.34 (17)
C2—C3—H3	120.0	C14—C10—C11	118.15 (18)
C3—C4—C5	120.68 (18)	C14—C10—C9	121.73 (18)
C3—C4—H4	119.7	C11—C10—C9	120.07 (18)
C5—C4—H4	119.7	C12—C11—C10	118.88 (18)
O2—C5—C4	124.72 (18)	C12—C11—H11	120.6
O2—C5—C6	115.90 (17)	C10—C11—H11	120.6
C4—C5—C6	119.38 (18)	C13—C12—C11	118.77 (19)
O3—C6—C7	125.62 (18)	C13—C12—H12	120.6
O3—C6—C5	114.82 (17)	C11—C12—H12	120.6
C7—C6—C5	119.56 (18)	N2—C13—C12	123.12 (18)
C6—C7—C2	120.88 (19)	N2—C13—H13	118.4
C6—C7—H7	119.6	C12—C13—H13	118.4
C2—C7—H7	119.6	N2—C14—C10	123.34 (18)
O3—C8—H8A	109.5	N2—C14—H14	118.3
O3—C8—H8B	109.5	C10—C14—H14	118.3
H8A—C8—H8B	109.5

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···O1iv	0.98	2.59	3.381 (3)	137.
C8—H8C···O2i	0.98	2.55	3.337 (2)	138.
C13—H13···O1v	0.95	2.49	3.185 (3)	130.

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⋯O1iv	0.98	2.59	3.381 (3)	137
C8—H8C⋯O2i	0.98	2.55	3.337 (2)	138
C13—H13⋯O1v	0.95	2.49	3.185 (3)	130

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