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

In the title compound, C12H8BrN3O, the 4-bromo-phenol 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 intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules 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 inter-actions [inter-centroid distance = 3.7680 (17) Å], involving inversion-related mol-ecules, forming a three-dimensional structure.

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 = 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

Δρmax = 0.52 e Å−3

Δρmin = −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 ▸).

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

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

Click here for additional data file.

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

Click here for additional data file.

. 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.

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

C12H8BrN3O	F(000) = 576
Mr = 290.12	Dx = 1.856 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4475 reflections
a = 5.5906 (3) Å	θ = 1.0–30.0°
b = 12.9032 (7) Å	µ = 3.94 mm−1
c = 14.7622 (6) Å	T = 193 K
β = 102.836 (3)°	Plate, orange
V = 1038.28 (9) Å3	0.25 × 0.20 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	3017 independent reflections
Radiation source: sealed tube	1977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
phi and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	h = −7→4
Tmin = 0.457, Tmax = 0.721	k = −17→18
8584 measured reflections	l = −20→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.045P)2 + 0.5334P] where P = (Fo2 + 2Fc2)/3
3017 reflections	(Δ/σ)max = 0.002
159 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.84 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1	0.83482 (7)	0.58489 (3)	1.18198 (2)	0.03255 (13)
O1	0.0419 (4)	0.75774 (17)	0.87477 (15)	0.0274 (5)
H1	0.0891	0.8104	0.8502	0.041*
N1	0.7079 (5)	0.9288 (2)	0.95213 (18)	0.0226 (6)
N2	0.3311 (5)	0.91524 (19)	0.85876 (18)	0.0249 (6)
N3	0.8399 (5)	1.09033 (19)	0.89394 (18)	0.0242 (6)
C1	0.4545 (6)	0.7733 (2)	0.9701 (2)	0.0231 (7)
C2	0.6365 (6)	0.7295 (2)	1.0408 (2)	0.0248 (7)
H2	0.7917	0.7625	1.0592	0.030*
C3	0.5911 (6)	0.6389 (2)	1.0835 (2)	0.0245 (7)
C4	0.3660 (6)	0.5889 (2)	1.0569 (2)	0.0276 (7)
H4	0.3362	0.5266	1.0868	0.033*
C5	0.1866 (6)	0.6303 (3)	0.9869 (2)	0.0299 (8)
H5	0.0333	0.5959	0.9684	0.036*
C6	0.2276 (6)	0.7220 (2)	0.9429 (2)	0.0247 (7)
C7	0.4972 (6)	0.8720 (2)	0.9272 (2)	0.0229 (7)
C8	0.6765 (6)	1.0143 (2)	0.8952 (2)	0.0222 (6)
C9	0.4404 (6)	1.0061 (2)	0.8373 (2)	0.0233 (7)
C10	0.3592 (6)	1.0841 (2)	0.7730 (2)	0.0265 (7)
H10	0.1997	1.0834	0.7336	0.032*
C11	0.5249 (7)	1.1633 (2)	0.7697 (2)	0.0287 (7)
H11	0.4796	1.2182	0.7264	0.034*
C12	0.7572 (6)	1.1635 (3)	0.8290 (2)	0.0281 (7)
H12	0.8647	1.2189	0.8233	0.034*
H1N	0.843 (8)	0.912 (3)	0.998 (3)	0.034 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.0314 (2)	0.0314 (2)	0.0320 (2)	−0.00049 (16)	0.00116 (14)	0.00779 (15)
O1	0.0181 (12)	0.0281 (12)	0.0317 (12)	−0.0034 (9)	−0.0036 (9)	0.0059 (10)
N1	0.0197 (14)	0.0238 (14)	0.0231 (13)	−0.0013 (11)	0.0025 (11)	0.0028 (11)
N2	0.0211 (14)	0.0251 (14)	0.0264 (13)	−0.0024 (12)	0.0010 (11)	−0.0003 (11)
N3	0.0236 (14)	0.0224 (14)	0.0270 (14)	−0.0024 (11)	0.0063 (11)	0.0007 (11)
C1	0.0212 (17)	0.0236 (16)	0.0258 (16)	−0.0015 (12)	0.0079 (13)	−0.0015 (13)
C2	0.0195 (17)	0.0261 (17)	0.0281 (16)	−0.0050 (13)	0.0038 (13)	−0.0016 (13)
C3	0.0252 (18)	0.0223 (16)	0.0253 (16)	0.0027 (13)	0.0037 (13)	0.0003 (13)
C4	0.0292 (18)	0.0198 (15)	0.0343 (18)	−0.0048 (14)	0.0079 (14)	0.0019 (14)
C5	0.0261 (19)	0.0254 (18)	0.0381 (19)	−0.0082 (14)	0.0070 (15)	−0.0064 (15)
C6	0.0212 (17)	0.0274 (17)	0.0257 (16)	−0.0006 (13)	0.0055 (13)	−0.0049 (13)
C7	0.0192 (16)	0.0259 (16)	0.0235 (15)	−0.0018 (13)	0.0044 (13)	−0.0017 (13)
C8	0.0212 (16)	0.0251 (16)	0.0211 (15)	0.0012 (13)	0.0067 (12)	−0.0042 (13)
C9	0.0220 (17)	0.0248 (16)	0.0235 (15)	−0.0014 (13)	0.0056 (13)	−0.0007 (13)
C10	0.0232 (17)	0.0309 (17)	0.0232 (15)	0.0006 (15)	0.0004 (12)	−0.0014 (14)
C11	0.035 (2)	0.0248 (17)	0.0261 (17)	0.0003 (15)	0.0066 (14)	0.0036 (14)
C12	0.0287 (18)	0.0255 (17)	0.0315 (18)	−0.0025 (14)	0.0100 (14)	0.0014 (14)

Br1—C3	1.891 (3)	C2—H2	0.9500
O1—C6	1.356 (4)	C3—C4	1.391 (5)
O1—H1	0.8400	C4—C5	1.378 (5)
N1—C7	1.366 (4)	C4—H4	0.9500
N1—C8	1.375 (4)	C5—C6	1.393 (5)
N1—H1N	0.92 (4)	C5—H5	0.9500
N2—C7	1.333 (4)	C8—C9	1.407 (4)
N2—C9	1.390 (4)	C9—C10	1.390 (4)
N3—C8	1.344 (4)	C10—C11	1.387 (5)
N3—C12	1.352 (4)	C10—H10	0.9500
C1—C2	1.405 (4)	C11—C12	1.395 (5)
C1—C6	1.408 (4)	C11—H11	0.9500
C1—C7	1.465 (4)	C12—H12	0.9500
C2—C3	1.378 (4)
C6—O1—H1	109.5	O1—C6—C5	117.2 (3)
C7—N1—C8	106.2 (3)	O1—C6—C1	123.0 (3)
C7—N1—H1N	126 (2)	C5—C6—C1	119.9 (3)
C8—N1—H1N	127 (2)	N2—C7—N1	113.2 (3)
C7—N2—C9	104.9 (3)	N2—C7—C1	122.6 (3)
C8—N3—C12	113.1 (3)	N1—C7—C1	124.3 (3)
C2—C1—C6	118.7 (3)	N3—C8—N1	126.8 (3)
C2—C1—C7	120.7 (3)	N3—C8—C9	126.6 (3)
C6—C1—C7	120.6 (3)	N1—C8—C9	106.6 (3)
C3—C2—C1	120.3 (3)	C10—C9—N2	132.3 (3)
C3—C2—H2	119.8	C10—C9—C8	118.7 (3)
C1—C2—H2	119.8	N2—C9—C8	109.0 (3)
C2—C3—C4	120.8 (3)	C11—C10—C9	116.0 (3)
C2—C3—Br1	119.4 (2)	C11—C10—H10	122.0
C4—C3—Br1	119.9 (2)	C9—C10—H10	122.0
C5—C4—C3	119.6 (3)	C10—C11—C12	121.0 (3)
C5—C4—H4	120.2	C10—C11—H11	119.5
C3—C4—H4	120.2	C12—C11—H11	119.5
C4—C5—C6	120.7 (3)	N3—C12—C11	124.6 (3)
C4—C5—H5	119.6	N3—C12—H12	117.7
C6—C5—H5	119.6	C11—C12—H12	117.7
C6—C1—C2—C3	−1.1 (5)	C6—C1—C7—N2	−3.0 (5)
C7—C1—C2—C3	177.2 (3)	C2—C1—C7—N1	−1.0 (5)
C1—C2—C3—C4	0.6 (5)	C6—C1—C7—N1	177.3 (3)
C1—C2—C3—Br1	−177.4 (2)	C12—N3—C8—N1	179.0 (3)
C2—C3—C4—C5	0.1 (5)	C12—N3—C8—C9	0.0 (5)
Br1—C3—C4—C5	178.1 (3)	C7—N1—C8—N3	−178.5 (3)
C3—C4—C5—C6	−0.4 (5)	C7—N1—C8—C9	0.7 (3)
C4—C5—C6—O1	−179.9 (3)	C7—N2—C9—C10	−179.5 (3)
C4—C5—C6—C1	−0.1 (5)	C7—N2—C9—C8	0.3 (4)
C2—C1—C6—O1	−179.4 (3)	N3—C8—C9—C10	−1.6 (5)
C7—C1—C6—O1	2.3 (5)	N1—C8—C9—C10	179.2 (3)
C2—C1—C6—C5	0.8 (5)	N3—C8—C9—N2	178.6 (3)
C7—C1—C6—C5	−177.5 (3)	N1—C8—C9—N2	−0.6 (4)
C9—N2—C7—N1	0.2 (4)	N2—C9—C10—C11	−178.4 (3)
C9—N2—C7—C1	−179.6 (3)	C8—C9—C10—C11	1.9 (4)
C8—N1—C7—N2	−0.6 (4)	C9—C10—C11—C12	−0.8 (5)
C8—N1—C7—C1	179.2 (3)	C8—N3—C12—C11	1.3 (5)
C2—C1—C7—N2	178.7 (3)	C10—C11—C12—N3	−0.9 (5)

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)

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)

Symmetry codes: (i) ; (ii) .