4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate.

In the mol-ecule of the title compound, C(15)H(12)BrN(3)·H(2)O, the phenyl ring is coplanar with the imidazopyridine ring system [dihedral angle = 0.4 (1)°]. The water mol-ecule is disordered over two positions with occupancies of 0.58 (1) and 0.42 (1), and it is linked to the main mol-ecule via an O-H⋯N hydrogen bond.

Related literature

For a related structure, see: Ouzidan et al. (2010 ▶).

Experimental

Crystal data

C15H12BrN3·H2O

M = 332.20

Triclinic,

a = 7.4363 (1) Å

b = 9.4238 (1) Å

c = 11.0829 (2) Å

α = 68.076 (1)°

β = 74.637 (1)°

γ = 79.736 (1)°

V = 692.02 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.97 mm−1

T = 293 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.588, T max = 0.664

14314 measured reflections

3158 independent reflections

2791 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.078

S = 0.98

3158 reflections

203 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025122/ci5117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025122/ci5117Isup2.hkl

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

C15H12BrN3·H2O	Z = 2
Mr = 332.20	F(000) = 336
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4363 (1) Å	Cell parameters from 7204 reflections
b = 9.4238 (1) Å	θ = 2.3–27.2°
c = 11.0829 (2) Å	µ = 2.97 mm−1
α = 68.076 (1)°	T = 293 K
β = 74.637 (1)°	Prism, yellow
γ = 79.736 (1)°	0.20 × 0.20 × 0.15 mm
V = 692.02 (2) Å3

Bruker X8 APEXII area-detector diffractometer	3158 independent reflections
Radiation source: fine-focus sealed tube	2791 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.588, Tmax = 0.664	k = −12→12
14314 measured reflections	l = −13→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.1091P] where P = (Fo2 + 2Fc2)/3
3158 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.25 e Å−3
6 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.78351 (3)	0.73753 (2)	0.425170 (19)	0.05007 (9)
O1	1.1389 (9)	0.1942 (6)	0.8855 (4)	0.0635 (16)	0.582 (14)
H11	1.028 (3)	0.229 (7)	0.903 (7)	0.095*	0.582 (14)
H12	1.208 (6)	0.237 (6)	0.908 (6)	0.095*	0.582 (14)
O1'	1.0501 (14)	0.1260 (12)	0.8987 (6)	0.081 (3)	0.418 (14)
H13	1.089 (17)	0.191 (10)	0.917 (11)	0.122*	0.418 (14)
H14	1.001 (16)	0.059 (9)	0.969 (6)	0.122*	0.418 (14)
N1	0.61186 (19)	0.78390 (15)	0.79149 (15)	0.0323 (3)
N2	0.66816 (19)	0.61173 (15)	1.00435 (15)	0.0347 (3)
N3	0.82874 (19)	0.41411 (16)	0.93153 (16)	0.0358 (3)
C1	0.6432 (2)	0.80592 (19)	0.66074 (18)	0.0350 (3)
H1	0.5976	0.8977	0.6035	0.042*
C2	0.7415 (2)	0.6947 (2)	0.61055 (19)	0.0368 (4)
C3	0.8123 (2)	0.55420 (19)	0.69201 (19)	0.0371 (4)
H3	0.8780	0.4791	0.6576	0.044*
C4	0.7798 (2)	0.53257 (18)	0.82533 (18)	0.0331 (3)
C5	0.6797 (2)	0.65118 (18)	0.87503 (17)	0.0313 (3)
C6	0.5091 (2)	0.90590 (19)	0.84527 (19)	0.0381 (4)
H6A	0.4210	0.9672	0.7908	0.046*
H6B	0.4386	0.8587	0.9352	0.046*
C7	0.6408 (3)	1.0068 (2)	0.8464 (2)	0.0481 (5)
H7	0.7367	0.9607	0.8917	0.058*
C8	0.6310 (5)	1.1541 (3)	0.7888 (3)	0.0711 (7)
H8A	0.5368	1.2037	0.7427	0.085*
H8B	0.7180	1.2105	0.7933	0.085*
C9	0.7604 (2)	0.46733 (18)	1.03315 (18)	0.0339 (3)
C10	0.7799 (2)	0.37743 (19)	1.17031 (18)	0.0354 (4)
C11	0.7034 (3)	0.4364 (2)	1.2724 (2)	0.0422 (4)
H11A	0.6407	0.5342	1.2535	0.051*
C12	0.7194 (3)	0.3511 (3)	1.4024 (2)	0.0498 (5)
H12A	0.6678	0.3919	1.4699	0.060*
C13	0.8118 (3)	0.2058 (3)	1.4313 (2)	0.0522 (5)
H13A	0.8219	0.1481	1.5184	0.063*
C14	0.8890 (3)	0.1467 (2)	1.3309 (2)	0.0509 (5)
H14A	0.9520	0.0490	1.3505	0.061*
C15	0.8741 (3)	0.2306 (2)	1.2012 (2)	0.0436 (4)
H15	0.9269	0.1892	1.1342	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.06412 (15)	0.05036 (14)	0.03761 (13)	0.00253 (9)	−0.01310 (9)	−0.01926 (9)
O1	0.076 (3)	0.056 (2)	0.068 (2)	0.020 (2)	−0.0289 (19)	−0.0341 (17)
O1'	0.091 (5)	0.084 (5)	0.074 (3)	0.022 (4)	−0.021 (3)	−0.044 (3)
N1	0.0350 (7)	0.0260 (6)	0.0359 (8)	0.0023 (5)	−0.0108 (6)	−0.0108 (5)
N2	0.0360 (7)	0.0294 (7)	0.0370 (8)	0.0013 (5)	−0.0094 (6)	−0.0104 (6)
N3	0.0352 (7)	0.0288 (7)	0.0422 (8)	0.0013 (5)	−0.0112 (6)	−0.0107 (6)
C1	0.0373 (8)	0.0307 (8)	0.0371 (9)	0.0006 (6)	−0.0122 (7)	−0.0106 (7)
C2	0.0394 (8)	0.0368 (9)	0.0373 (9)	−0.0032 (7)	−0.0104 (7)	−0.0148 (7)
C3	0.0382 (8)	0.0321 (8)	0.0435 (10)	0.0008 (6)	−0.0084 (7)	−0.0181 (7)
C4	0.0307 (7)	0.0276 (7)	0.0418 (9)	0.0004 (6)	−0.0095 (7)	−0.0129 (7)
C5	0.0302 (7)	0.0274 (7)	0.0368 (9)	−0.0010 (6)	−0.0083 (6)	−0.0116 (6)
C6	0.0422 (9)	0.0305 (8)	0.0394 (9)	0.0086 (7)	−0.0097 (7)	−0.0143 (7)
C7	0.0513 (11)	0.0487 (11)	0.0530 (12)	0.0017 (8)	−0.0112 (9)	−0.0303 (9)
C8	0.101 (2)	0.0508 (13)	0.0645 (16)	−0.0212 (13)	−0.0088 (14)	−0.0227 (12)
C9	0.0293 (7)	0.0299 (8)	0.0402 (9)	−0.0027 (6)	−0.0087 (6)	−0.0085 (7)
C10	0.0318 (8)	0.0307 (8)	0.0407 (9)	−0.0048 (6)	−0.0107 (7)	−0.0058 (7)
C11	0.0443 (9)	0.0376 (9)	0.0419 (10)	−0.0011 (7)	−0.0118 (8)	−0.0101 (7)
C12	0.0521 (11)	0.0543 (12)	0.0419 (11)	−0.0061 (9)	−0.0123 (9)	−0.0132 (9)
C13	0.0524 (11)	0.0521 (12)	0.0427 (11)	−0.0107 (9)	−0.0178 (9)	0.0021 (9)
C14	0.0495 (11)	0.0370 (10)	0.0561 (13)	−0.0005 (8)	−0.0199 (9)	−0.0006 (9)
C15	0.0432 (9)	0.0348 (9)	0.0482 (11)	0.0000 (7)	−0.0120 (8)	−0.0093 (8)

Br1—C2	1.8887 (19)	C6—C7	1.487 (3)
O1—H11	0.834 (10)	C6—H6A	0.97
O1—H12	0.838 (10)	C6—H6B	0.97
O1—H13	0.43 (12)	C7—C8	1.291 (3)
O1'—H11	0.97 (5)	C7—H7	0.93
O1'—H13	0.836 (10)	C8—H8A	0.93
O1'—H14	0.838 (10)	C8—H8B	0.93
N1—C1	1.346 (2)	C9—C10	1.470 (3)
N1—C5	1.354 (2)	C10—C11	1.389 (3)
N1—C6	1.489 (2)	C10—C15	1.396 (2)
N2—C5	1.322 (2)	C11—C12	1.388 (3)
N2—C9	1.372 (2)	C11—H11A	0.93
N3—C9	1.344 (2)	C12—C13	1.379 (3)
N3—C4	1.365 (2)	C12—H12A	0.93
C1—C2	1.375 (2)	C13—C14	1.374 (3)
C1—H1	0.93	C13—H13A	0.93
C2—C3	1.398 (2)	C14—C15	1.381 (3)
C3—C4	1.374 (3)	C14—H14A	0.93
C3—H3	0.93	C15—H15	0.93
C4—C5	1.433 (2)
H11—O1—H12	110.6 (18)	H6A—C6—H6B	108.0
H12—O1—H13	101 (6)	C8—C7—C6	124.3 (2)
H11—O1'—H14	114 (9)	C8—C7—H7	117.8
H13—O1'—H14	110.2 (19)	C6—C7—H7	117.8
C1—N1—C5	119.78 (14)	C7—C8—H8A	120.0
C1—N1—C6	120.89 (14)	C7—C8—H8B	120.0
C5—N1—C6	119.29 (14)	H8A—C8—H8B	120.0
C5—N2—C9	101.46 (14)	N3—C9—N2	117.02 (16)
C9—N3—C4	103.09 (13)	N3—C9—C10	122.81 (15)
N1—C1—C2	120.95 (16)	N2—C9—C10	120.17 (16)
N1—C1—H1	119.5	C11—C10—C15	118.49 (18)
C2—C1—H1	119.5	C11—C10—C9	120.61 (16)
C1—C2—C3	122.00 (17)	C15—C10—C9	120.90 (17)
C1—C2—Br1	117.99 (14)	C12—C11—C10	120.79 (18)
C3—C2—Br1	120.01 (13)	C12—C11—H11A	119.6
C4—C3—C2	116.73 (15)	C10—C11—H11A	119.6
C4—C3—H3	121.6	C13—C12—C11	120.0 (2)
C2—C3—H3	121.6	C13—C12—H12A	120.0
N3—C4—C3	132.84 (15)	C11—C12—H12A	120.0
N3—C4—C5	106.85 (15)	C14—C13—C12	119.7 (2)
C3—C4—C5	120.29 (15)	C14—C13—H13A	120.1
N2—C5—N1	128.19 (15)	C12—C13—H13A	120.1
N2—C5—C4	111.57 (14)	C13—C14—C15	120.79 (19)
N1—C5—C4	120.24 (16)	C13—C14—H14A	119.6
C7—C6—N1	110.95 (14)	C15—C14—H14A	119.6
C7—C6—H6A	109.4	C14—C15—C10	120.2 (2)
N1—C6—H6A	109.4	C14—C15—H15	119.9
C7—C6—H6B	109.4	C10—C15—H15	119.9
N1—C6—H6B	109.4
C5—N1—C1—C2	0.8 (2)	C1—N1—C6—C7	−91.40 (19)
C6—N1—C1—C2	178.59 (16)	C5—N1—C6—C7	86.45 (19)
N1—C1—C2—C3	0.4 (3)	N1—C6—C7—C8	124.1 (2)
N1—C1—C2—Br1	−178.60 (12)	C4—N3—C9—N2	0.46 (19)
C1—C2—C3—C4	−0.4 (3)	C4—N3—C9—C10	179.96 (15)
Br1—C2—C3—C4	178.57 (12)	C5—N2—C9—N3	0.11 (19)
C9—N3—C4—C3	177.66 (18)	C5—N2—C9—C10	−179.41 (14)
C9—N3—C4—C5	−0.79 (17)	N3—C9—C10—C11	−178.67 (16)
C2—C3—C4—N3	−178.94 (17)	N2—C9—C10—C11	0.8 (2)
C2—C3—C4—C5	−0.7 (2)	N3—C9—C10—C15	0.8 (2)
C9—N2—C5—N1	179.89 (16)	N2—C9—C10—C15	−179.71 (15)
C9—N2—C5—C4	−0.63 (17)	C15—C10—C11—C12	−0.3 (3)
C1—N1—C5—N2	177.63 (16)	C9—C10—C11—C12	179.18 (17)
C6—N1—C5—N2	−0.2 (3)	C10—C11—C12—C13	−0.1 (3)
C1—N1—C5—C4	−1.8 (2)	C11—C12—C13—C14	0.5 (3)
C6—N1—C5—C4	−179.69 (15)	C12—C13—C14—C15	−0.4 (3)
N3—C4—C5—N2	0.95 (19)	C13—C14—C15—C10	0.0 (3)
C3—C4—C5—N2	−177.74 (14)	C11—C10—C15—C14	0.4 (3)
N3—C4—C5—N1	−179.52 (14)	C9—C10—C15—C14	−179.12 (16)
C3—C4—C5—N1	1.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···N3	0.83 (1)	2.14 (3)	2.887 (4)	149 (5)
O1—H12···N2i	0.84 (1)	2.41 (2)	3.229 (7)	165 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯N3	0.83 (1)	2.14 (3)	2.887 (4)	149 (5)