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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3168
https://doi.org/10.1107/S1600536811045648

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

Fiona N.-F. How,a M. S. Amalina,a Hamid Khaledib* and Hapipah Mohd Alib

aDepartment of Biomedical Sciences, Kulliyah of Science, IIUM Kuantan, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200 Kuantan, Pahang Darul Makmur, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 24 October 2011; accepted 31 October 2011; online 5 November 2011)

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[Miwa, Y., Mizuno, T., Tsuchida, K., Taga, T. & Iwata, Y. (1999). Acta Cryst. B55, 78-84.]); Li et al. (2011[Li, J., Bourne, S. A. & Caira, M. R. (2011). Chem. Commun. 47, 1530-1532.]). For the structure of vanillin, see: Velavan et al. (1995[Velavan, R., Sureshkumar, P., Sivakumar, K. & Natarajan, S. (1995). Acta Cryst. C51, 1131-1133.]).

[Scheme 1]

Experimental

Crystal data

  • C6H6N2O·C8H8O3

  • Mr = 274.27

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.996

  • 3432 measured reflections

  • 2243 independent reflections

  • 1862 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

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) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem, 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045648/pv2471sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045648/pv2471Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045648/pv2471Isup3.cml

checkCIF report


Comment top

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.

Related literature top

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 top

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.

Refinement top

The C-bound H atoms were placed at calculated positions and were treated as riding on their parent C atoms with C—H distances of 0.95 (aryl) and 0.98 (methyl) Å. The N– and O-bound H atoms were located in a difference Fourier map, and refined with distance restraints of O—H = 0.84 (2) Å and N—H = 0.88 (2) Å. For all H atoms, Uiso(H) was set to 1.2–1.5eq(carrier atom). An additional rigid-bond type restraint (DELU in SHELXL97) was placed on the displacement parameters of C1 and C2.

Structure description top

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.

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.
[Figure 2] Fig. 2. A chain along the a axis formed by N—H···O and O—H···N hydrogen bonds.
4-Hydroxy-3-methoxybenzaldehyde–nicotinamide (1/1) top
Crystal data top
C6H6N2O·C8H8O3Z = 2
Mr = 274.27F(000) = 288
Triclinic, P1Dx = 1.429 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8979 (1) ÅCell parameters from 1226 reflections
b = 8.5440 (2) Åθ = 2.6–29.7°
c = 15.4713 (4) ŵ = 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
Data collection top
Bruker APEXII CCD
diffractometer		2243 independent reflections
Radiation source: fine-focus sealed tube1862 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→5
Tmin = 0.977, Tmax = 0.996k = −10→10
3432 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H 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 parametersΔρmax = 0.66 e Å−3
4 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C6H6N2O·C8H8O3γ = 94.784 (2)°
Mr = 274.27V = 637.52 (3) Å3
Triclinic, P1Z = 2
a = 4.8979 (1) ÅMo Kα radiation
b = 8.5440 (2) ŵ = 0.11 mm−1
c = 15.4713 (4) ÅT = 100 K
α = 98.108 (1)°0.22 × 0.14 × 0.04 mm
β = 92.810 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2243 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1862 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.996Rint = 0.019
3432 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.66 e Å−3
2243 reflectionsΔρmin = −0.28 e Å−3
191 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3651 (3)0.83011 (19)0.61085 (10)0.0359 (4)
O20.8107 (3)0.63328 (16)0.23075 (9)0.0195 (3)
H20.949 (4)0.698 (2)0.2250 (15)0.029*
O30.4028 (3)0.44026 (16)0.25734 (9)0.0218 (3)
C10.3070 (5)0.7306 (3)0.54863 (14)0.0286 (5)
H10.15290.65700.55220.034*
C20.4516 (4)0.7113 (2)0.46701 (13)0.0210 (4)
C30.6726 (4)0.8148 (2)0.45164 (13)0.0221 (5)
H30.73800.90160.49510.026*
C40.7972 (4)0.7912 (2)0.37307 (13)0.0204 (4)
H40.94820.86200.36290.024*
C50.7035 (4)0.6648 (2)0.30888 (12)0.0166 (4)
C60.4793 (4)0.5600 (2)0.32443 (12)0.0176 (4)
C70.3561 (4)0.5847 (2)0.40255 (13)0.0208 (5)
H70.20400.51460.41280.025*
C80.1709 (4)0.3323 (2)0.26827 (14)0.0217 (5)
H8A0.21100.27650.31790.033*
H8B0.13280.25510.21500.033*
H8C0.01030.39170.27930.033*
O40.8254 (3)0.71964 (19)−0.04761 (9)0.0299 (4)
N10.3766 (4)0.6341 (2)−0.07875 (11)0.0205 (4)
H1A0.207 (3)0.645 (3)−0.0672 (14)0.025*
H1B0.415 (4)0.586 (2)−0.1293 (11)0.025*
N20.2385 (3)0.80224 (19)0.18395 (10)0.0170 (4)
C90.5840 (4)0.7129 (2)−0.02755 (13)0.0197 (4)
C100.5123 (4)0.7959 (2)0.05932 (12)0.0169 (4)
C110.6653 (4)0.9350 (2)0.09779 (13)0.0201 (4)
H110.81210.98010.06870.024*
C120.5998 (4)1.0066 (2)0.17913 (13)0.0220 (5)
H120.69971.10230.20660.026*
C130.3864 (4)0.9363 (2)0.21971 (13)0.0192 (4)
H130.34290.98560.27570.023*
C140.3015 (4)0.7346 (2)0.10499 (12)0.0162 (4)
H140.19660.63970.07880.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0440 (10)0.0363 (9)0.0266 (9)0.0056 (8)0.0038 (7)0.0006 (7)
O20.0182 (8)0.0217 (7)0.0174 (7)−0.0031 (6)0.0053 (6)0.0004 (6)
O30.0223 (8)0.0214 (7)0.0198 (7)−0.0045 (6)0.0064 (6)−0.0016 (6)
C10.0356 (13)0.0308 (12)0.0189 (10)0.0104 (10)−0.0028 (9)−0.0012 (9)
C20.0226 (11)0.0246 (11)0.0170 (10)0.0074 (8)0.0004 (8)0.0045 (8)
C30.0270 (11)0.0214 (10)0.0165 (10)0.0060 (9)−0.0036 (8)−0.0020 (8)
C40.0187 (10)0.0193 (10)0.0218 (11)−0.0018 (8)−0.0001 (8)0.0014 (8)
C50.0157 (10)0.0209 (10)0.0145 (9)0.0054 (8)0.0026 (8)0.0043 (8)
C60.0193 (10)0.0176 (10)0.0157 (10)0.0033 (8)0.0002 (8)0.0007 (8)
C70.0193 (11)0.0242 (11)0.0199 (10)0.0020 (8)0.0046 (8)0.0055 (8)
C80.0185 (11)0.0198 (10)0.0259 (11)−0.0031 (8)0.0035 (8)0.0021 (8)
O40.0144 (8)0.0516 (10)0.0228 (8)0.0064 (7)0.0038 (6)−0.0003 (7)
N10.0172 (9)0.0279 (9)0.0153 (9)0.0046 (7)0.0035 (7)−0.0030 (7)
N20.0171 (9)0.0194 (8)0.0148 (8)0.0031 (7)0.0012 (6)0.0027 (6)
C90.0178 (11)0.0255 (11)0.0168 (10)0.0055 (8)0.0018 (8)0.0042 (8)
C100.0144 (10)0.0210 (10)0.0156 (10)0.0038 (8)−0.0008 (7)0.0030 (8)
C110.0149 (10)0.0240 (10)0.0221 (10)0.0003 (8)0.0020 (8)0.0058 (8)
C120.0227 (11)0.0180 (10)0.0234 (11)−0.0030 (8)−0.0011 (8)−0.0002 (8)
C130.0217 (11)0.0192 (10)0.0160 (10)0.0031 (8)0.0002 (8)0.0001 (8)
C140.0157 (10)0.0162 (9)0.0161 (10)0.0009 (7)−0.0013 (8)0.0012 (7)
Geometric parameters (Å, º) top
O1—C11.197 (3)C8—H8B0.9800
O2—C51.343 (2)C8—H8C0.9800
O2—H20.854 (16)O4—C91.236 (2)
O3—C61.365 (2)N1—C91.330 (3)
O3—C81.435 (2)N1—H1A0.868 (16)
C1—C21.474 (3)N1—H1B0.869 (16)
C1—H10.9500N2—C131.336 (2)
C2—C31.391 (3)N2—C141.338 (2)
C2—C71.396 (3)C9—C101.500 (3)
C3—C41.384 (3)C10—C141.388 (3)
C3—H30.9500C10—C111.392 (3)
C4—C51.391 (3)C11—C121.384 (3)
C4—H40.9500C11—H110.9500
C5—C61.410 (3)C12—C131.384 (3)
C6—C71.375 (3)C12—H120.9500
C7—H70.9500C13—H130.9500
C8—H8A0.9800C14—H140.9500
C5—O2—H2112.6 (16)O3—C8—H8C109.5
C6—O3—C8117.44 (15)H8A—C8—H8C109.5
O1—C1—C2126.2 (2)H8B—C8—H8C109.5
O1—C1—H1116.9C9—N1—H1A121.6 (15)
C2—C1—H1116.9C9—N1—H1B117.5 (15)
C3—C2—C7119.56 (18)H1A—N1—H1B120 (2)
C3—C2—C1122.83 (19)C13—N2—C14117.72 (17)
C7—C2—C1117.59 (19)O4—C9—N1123.82 (19)
C4—C3—C2119.93 (19)O4—C9—C10119.84 (18)
C4—C3—H3120.0N1—C9—C10116.34 (17)
C2—C3—H3120.0C14—C10—C11118.15 (18)
C3—C4—C5120.68 (18)C14—C10—C9121.73 (18)
C3—C4—H4119.7C11—C10—C9120.07 (18)
C5—C4—H4119.7C12—C11—C10118.88 (18)
O2—C5—C4124.72 (18)C12—C11—H11120.6
O2—C5—C6115.90 (17)C10—C11—H11120.6
C4—C5—C6119.38 (18)C13—C12—C11118.77 (19)
O3—C6—C7125.62 (18)C13—C12—H12120.6
O3—C6—C5114.82 (17)C11—C12—H12120.6
C7—C6—C5119.56 (18)N2—C13—C12123.12 (18)
C6—C7—C2120.88 (19)N2—C13—H13118.4
C6—C7—H7119.6C12—C13—H13118.4
C2—C7—H7119.6N2—C14—C10123.34 (18)
O3—C8—H8A109.5N2—C14—H14118.3
O3—C8—H8B109.5C10—C14—H14118.3
H8A—C8—H8B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.87 (2)2.05 (2)2.900 (2)167 (2)
N1—H1B···O2ii0.87 (2)2.42 (2)3.085 (2)134 (2)
N1—H1B···O3ii0.87 (2)2.20 (2)3.019 (2)156 (2)
O2—H2···N2iii0.85 (2)1.80 (2)2.634 (2)164 (2)
C8—H8A···O1iv0.982.593.381 (3)137
C8—H8C···O2i0.982.553.337 (2)138
C13—H13···O1v0.952.493.185 (3)130
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC6H6N2O·C8H8O3
Mr274.27
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)4.8979 (1), 8.5440 (2), 15.4713 (4)
α, β, γ (°)98.108 (1), 92.810 (2), 94.784 (2)
V (Å3)637.52 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.22 × 0.14 × 0.04
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.977, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		3432, 2243, 1862
Rint0.019
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.112, 1.05
No. of reflections2243
No. of parameters191
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.66, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.868 (16)2.048 (17)2.900 (2)167 (2)
N1—H1B···O2ii0.869 (16)2.416 (19)3.085 (2)134.2 (18)
N1—H1B···O3ii0.869 (16)2.203 (18)3.019 (2)156 (2)
O2—H2···N2iii0.854 (16)1.801 (17)2.634 (2)164 (2)
C8—H8A···O1iv0.982.593.381 (3)137.4
C8—H8C···O2i0.982.553.337 (2)137.7
C13—H13···O1v0.952.493.185 (3)129.9
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3168
https://doi.org/10.1107/S1600536811045648
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