3-[(E)-(Pyridin-3-yl­imino)­meth­yl]phenol

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

doi:10.1107/S1600536812025822

. 2012 Jun 13;68(Pt 7):o2072. doi: 10.1107/S1600536812025822

3-[(E)-(Pyridin-3-ylimino)methyl]phenol

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

PMCID: PMC3393889 PMID: 22798754

Abstract

Two independent molecules are present in the asymmetric unit of the title compound, C₁₂H₁₀N₂O, in which the 3-hydroxybenzaldehyde and the pyridin-3-amine units are almost planar [r.m.s. deviations of 0.0236 and 0.0116Å, respectively, in one molecule and 0.0245 and 0.0162Å, respectively, in the other] and are oriented at dihedral angles of 7.21 (7) and 14.77 (7)°. In the crystal, molecules of the same type form inversion dimers via pairs of O—H⋯N hydrogen bonds, forming R ₂ ²(20) ring motifs. There exist π–π interactions between the benzene and pyridine rings of molecules of the same type with centroid–centroid distances of 3.7127 (10) and 3.8439 (10) Å.

Related literature

For a related structure, see: Wiebcke & Mootz (1982 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₁₀N₂O
M _r = 198.22
Triclinic,
a = 5.7768 (5) Å
b = 12.1450 (11) Å
c = 14.8194 (13) Å
α = 78.207 (4)°
β = 89.641 (3)°
γ = 77.601 (4)°
V = 993.26 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.957, T _max = 0.966
14798 measured reflections
3876 independent reflections
2704 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.118
S = 1.04
3876 reflections
261 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 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 (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/S1600536812025822/rk2365sup1.cif

e-68-o2072-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025822/rk2365Isup2.hkl

e-68-o2072-Isup2.hkl^{(186.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025822/rk2365Isup3.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
O1—H1⋯N2ⁱ	0.82	2.00	2.810 (2)	172
O2—H2A⋯N4ⁱⁱ	0.82	1.99	2.8058 (12)	174

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

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

In the crystal structure, (Fig. 1), of title compound, two molecules in the asymmetric unit are present, which differ slightly from each other geometrically. In one molecule, the 3-hydroxybenzaldehyde group A (C1–C7/O1) and the pyridin-3-amine moiety B (C8–C12/N1/N2) are planar with r.m.s. deviation of 0.0236Å and 0.0116Å, respectively. The dihedral angle between A/B is 14.78 (7)°. In second molecule, the similar groups C (C13–C19/O2) and D (C20–C24/N3/N4) are also planar with r.m.s. deviation of 0.0245Å and 0.0162Å, respectively and the dihedral angle between C/D is 7.21 (7)°. Both molecules are dimerized with themselves due to intermolecular H-bonding of O—H···N type (Table 1, Fig. 2) and form R₂²(20) ring motif (Bernstein et al., 1995). There exist π···π interaction between Cg1···Cg2ⁱⁱⁱ and Cg2···Cg1ⁱⁱⁱ at a distance of 3.8439 (11)Å. Similarly, there exist π···π interaction between Cg3···Cg4^iv and Cg4···Cg3^iv at a distance of 3.7126 (10)Å. Cg1, Cg2, Cg3 and Cg4 are the centroids of (C8–C12/N2), (C1–C6), (C20–C24/N4) and (C13–C18) rings, respectively. Symmetry codes: (iii) = -x, -y, -z; (iv) = -x, -y, -z+1.

The structure of related compounds - trans-N-benzylidene-3-pyridinamine has been published by Wiebcke & Mootz, 1982.

Experimental

The title compound has been synthesized as a derivative. Equimolar quantities of 3-hydroxybenzaldehyde and pyridin-3-amine were refluxed in methanol along with few drops of acetic acid as catalyst for 30 min resulting in colourless solution. The solution was kept at room temperature which affoarded colourless prisms after three days.