Crystal structure of 4-bromo-2-(1H-imidazo[4,5-b]pyridin-2-yl)phenol

Kamel Ouari

doi:10.1107/S2056989015022197

. 2015 Nov 28;71(Pt 12):o991–o992. doi: 10.1107/S2056989015022197

Crystal structure of 4-bromo-2-(1H-imidazo[4,5-b]pyridin-2-yl)phenol

Kamel Ouari ^a,^*

PMCID: PMC4719939 PMID: 26870567

Abstract

In the title compound, C₁₂H₈BrN₃O, the 4-bromophenol ring is coplanar with the planar imidazo[4,5-b]pyridine moiety (r.m.s deviation = 0.015 Å), making a dihedral angle of 1.8 (2)°. There is an intramolecular O—H⋯N hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked via N—H⋯N and O—H⋯Br hydrogen bonds, forming undulating sheets parallel to (10-2). The sheets are linked by π–π interactions [inter-centroid distance = 3.7680 (17) Å], involving inversion-related molecules, forming a three-dimensional structure.

Keywords: crystal structure; 2,3-diaminopyridine; 5-bromo-2-hydroxy-1-salycilaldehyde; hydrogen bonding

Related literature

For some recent examples of transition metal complexes of Schiff bases, see: Ouari et al. (2015b ▸); Benghanem et al. (2012 ▸); Basu et al. (2010 ▸). For the biological activity of Schiff bases, see: Yıldız et al. (2015 ▸); Salama et al. (2015 ▸); Zayed et al. (2015 ▸). For the photoluminescence of the title compound, see: Köse et al. (2015 ▸); Pal et al. (2015 ▸); Ray et al. (2014 ▸). For the literature method used to prepare the title compound, see: Ouari et al. (2015a ▸). For the crystal structure of a related compound, see: Belguedj et al. (2015 ▸).

Experimental

Crystal data

C₁₂H₈BrN₃O
M _r = 290.12
Monoclinic,
a = 5.5906 (3) Å
b = 12.9032 (7) Å
c = 14.7622 (6) Å
β = 102.836 (3)°
V = 1038.28 (9) Å³
Z = 4
Mo Kα radiation
μ = 3.94 mm⁻¹
T = 193 K
0.25 × 0.20 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009 ▸) T _min = 0.457, T _max = 0.721
8584 measured reflections
3017 independent reflections
1977 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.111
S = 1.02
3017 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▸); cell refinement: DENZO (Nonius, 1998 ▸); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989015022197/su5238sup1.cif

e-71-0o991-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022197/su5238Isup2.hkl

e-71-0o991-Isup2.hkl^{(145.1KB, hkl)}

Click here for additional data file.^{(4.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015022197/su5238Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015022197/su5238fig1.tif

The molecular structure of the title compound, with atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O-H⋯N hydrogen bond is shown as a dashed line (see Table 1).

Click here for additional data file.^{(1.9MB, tif)}

c . DOI: 10.1107/S2056989015022197/su5238fig2.tif

A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1), and H atoms not involved in these interactions have been omitted for clarity.

CCDC reference: 1437912

Additional supporting information: 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⋯N2	0.84	1.90	2.640 (3)	147
O1—H1⋯Br1ⁱ	0.84	2.91	3.478 (2)	127
N1—H1N⋯N3ⁱⁱ	0.92 (4)	2.11 (4)	3.010 (4)	168 (3)

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

Acknowledgments

The author gratefully acknowledges financial support from the Algerian Ministry of Higher Education and Scientific Research. He also acknowledges the help of Dr Jean Weiss (CLAC) at the University of Strasbourg, France.

supplementary crystallographic information

S1. Comment

Coordination chemistry of transition metal complexes with Schiff base ligands is an important and fascinating branch of chemistry (Ouari et al., 2015b; Benghanem et al., 2012; Basu et al., 2010). A literature survey revealed that this kind of compound possesses diverse biological activities such as antibiotic (Yıldız et al., 2015) and antimicrobial (Salama et al., 2015; Zayed et al., 2015). The photoluminescence of the title compound has been reported (Köse et al., 2015; Pal et al., 2015; Ray et al., 2014).

The molecular structure of the title compound is shown in Fig. 1. The bond distances and angles are normal and similar to those in related compounds (Belguedj et al., 2015).

In the crystal, molecules are linked via N—H···N and O—H···Br hydrogen bonds forming undulating sheets parallel to (102); see Table 1 and Fig. 2. The sheets are linked by π-π interactions [Cg2···Cg3ⁱ = 3.7680 (17) Å, Cg2 and Cg3 are the centroids of rings N3/C8—C12 and C1—C6, symmetry code: (i) - x + 1, - y + 2, - z + 2], forming a three-dimensional structure.

S2. Synthesis and crystallisation

The title compound was prepared following a literature method (Ouari et al., 2015a). To a MeOH solution (15 ml) of 5-bromosalicylaldehyde (0.122 g, 1 mmol) was added drop wise to a MeOH solution (5 ml) of 2,3-diaminopyridine (0.109 g, 1 mmol). The mixture was refluxed with constant stirring under a nitrogen atmosphere for 3 h, yielding an abundant orange precipitate that was collected by filtration. The product was washed with methanol (3 × 5 ml) then with diethyl ether (3 × 5 ml) and dried under vacuum for 4 h. Orange crystals of the title compound, suitable for X-ray diffraction analysis, were obtained after two weeks by slow evaporation of the DMSO solvent (yield: 70%; m.p.: 528-531 K).

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The iminium H atom was located from a difference Fourier map and freely refined. The OH and C-bound H atoms were included in calculated positions and treated as riding atoms: O—H = 0.82 Å, C—H = 0.95-0.99 Å with U_iso(H) = 1.5U_eq(O) and 1.2U_eq(C).