3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine.

In the title mol-ecule, C(17)H(12)BrN(3)O, the imidazopyridine ring system is almost coplanar with the furan ring [dihedral angle = 2.0 (3)°]. The benzyl phenyl ring is oriented at dihedral angles of 85.2 (2) and 85.5 (1)°, respectively, with respect to the furan ring and the imidazopyridine ring system. In the crystal, mol-ecules are linked into chains propagating along the b axis by C-H⋯N hydrogen bonds. Adjacent chains are linked via short Br⋯Br contacts [3.493 (1) Å].

Related literature

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

Experimental

Crystal data

C17H12BrN3O

M = 354.21

Monoclinic,

a = 15.8422 (3) Å

b = 5.4747 (1) Å

c = 18.4243 (3) Å

β = 111.509 (1)°

V = 1486.68 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.77 mm−1

T = 293 K

0.25 × 0.25 × 0.10 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.544, T max = 0.769

19471 measured reflections

2614 independent reflections

2105 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.110

S = 0.97

2614 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.44 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/S160053681002475X/ci5113sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002475X/ci5113Isup2.hkl

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

C17H12BrN3O	F(000) = 712
Mr = 354.21	Dx = 1.583 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5830 reflections
a = 15.8422 (3) Å	θ = 2.7–23.3°
b = 5.4747 (1) Å	µ = 2.77 mm−1
c = 18.4243 (3) Å	T = 293 K
β = 111.509 (1)°	Prism, orange
V = 1486.68 (5) Å3	0.25 × 0.25 × 0.10 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	2614 independent reflections
Radiation source: fine-focus sealed tube	2105 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→18
Tmin = 0.544, Tmax = 0.769	k = −6→5
19471 measured reflections	l = −21→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0848P)2 + 0.0891P] where P = (Fo2 + 2Fc2)/3
2614 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.47189 (2)	1.27997 (6)	0.426257 (19)	0.05859 (18)
O1	0.21672 (14)	0.1051 (4)	0.11117 (12)	0.0605 (6)
N1	0.28026 (15)	0.7379 (4)	0.34628 (14)	0.0407 (6)
N2	0.26035 (13)	0.4610 (4)	0.23929 (12)	0.0362 (5)
N3	0.37245 (14)	0.6006 (4)	0.20155 (13)	0.0415 (5)
C1	0.33253 (18)	0.9234 (5)	0.38466 (16)	0.0437 (6)
H1	0.3214	0.9916	0.4265	0.052*
C2	0.40263 (16)	1.0193 (5)	0.36533 (15)	0.0399 (6)
C3	0.42374 (17)	0.9297 (5)	0.30393 (15)	0.0400 (6)
H3	0.4701	0.9949	0.2904	0.048*
C4	0.37115 (19)	0.7370 (4)	0.26428 (18)	0.0364 (6)
C5	0.30126 (16)	0.6536 (5)	0.28810 (15)	0.0347 (6)
C6	0.18408 (17)	0.3215 (5)	0.24445 (16)	0.0398 (6)
H6A	0.1851	0.3335	0.2973	0.048*
H6B	0.1923	0.1509	0.2344	0.048*
C7	0.09249 (16)	0.4032 (4)	0.18891 (15)	0.0373 (6)
C8	0.0798 (2)	0.6091 (6)	0.1437 (2)	0.0660 (9)
H8	0.1294	0.7050	0.1467	0.079*
C9	−0.0063 (3)	0.6757 (7)	0.0935 (3)	0.0863 (13)
H9	−0.0139	0.8138	0.0623	0.104*
C10	−0.0799 (2)	0.5399 (7)	0.0897 (2)	0.0752 (10)
H10	−0.1375	0.5839	0.0556	0.090*
C11	−0.0687 (2)	0.3409 (8)	0.1356 (2)	0.0706 (10)
H11	−0.1190	0.2505	0.1340	0.085*
C12	0.0171 (2)	0.2703 (5)	0.1851 (2)	0.0549 (8)
H12	0.0239	0.1319	0.2160	0.066*
C13	0.30648 (16)	0.4385 (5)	0.18846 (15)	0.0369 (6)
C14	0.2871 (2)	0.2623 (4)	0.12615 (18)	0.0428 (7)
C15	0.3289 (2)	0.2287 (6)	0.0754 (2)	0.0587 (9)
H15	0.3787	0.3147	0.0737	0.070*
C16	0.2825 (2)	0.0376 (6)	0.02513 (19)	0.0651 (9)
H16	0.2956	−0.0266	−0.0163	0.078*
C17	0.2169 (3)	−0.0318 (6)	0.04850 (19)	0.0683 (9)
H17	0.1761	−0.1570	0.0257	0.082*

	U11	U22	U33	U12	U13	U23
Br1	0.0540 (3)	0.0519 (2)	0.0593 (3)	−0.00676 (12)	0.00831 (18)	−0.01181 (13)
O1	0.0659 (14)	0.0602 (13)	0.0594 (14)	−0.0183 (11)	0.0276 (11)	−0.0162 (10)
N1	0.0330 (13)	0.0534 (13)	0.0395 (14)	0.0029 (9)	0.0176 (11)	−0.0003 (10)
N2	0.0268 (11)	0.0449 (11)	0.0378 (13)	−0.0025 (9)	0.0130 (9)	−0.0003 (9)
N3	0.0317 (12)	0.0538 (14)	0.0424 (13)	−0.0020 (10)	0.0175 (10)	−0.0037 (10)
C1	0.0380 (15)	0.0519 (15)	0.0416 (16)	0.0036 (12)	0.0150 (12)	−0.0047 (12)
C2	0.0330 (14)	0.0416 (13)	0.0391 (16)	0.0017 (11)	0.0061 (12)	−0.0006 (11)
C3	0.0296 (14)	0.0464 (14)	0.0440 (16)	−0.0006 (11)	0.0135 (12)	0.0030 (11)
C4	0.0281 (15)	0.0436 (14)	0.0396 (17)	0.0007 (10)	0.0147 (13)	0.0028 (11)
C5	0.0253 (13)	0.0419 (13)	0.0361 (15)	0.0025 (10)	0.0101 (11)	0.0027 (11)
C6	0.0345 (15)	0.0458 (14)	0.0414 (16)	−0.0046 (11)	0.0165 (13)	0.0047 (11)
C7	0.0288 (13)	0.0408 (13)	0.0437 (16)	−0.0052 (10)	0.0152 (12)	−0.0047 (11)
C8	0.0388 (17)	0.063 (2)	0.086 (2)	−0.0040 (14)	0.0108 (17)	0.0219 (17)
C9	0.062 (2)	0.069 (2)	0.102 (3)	0.0088 (19)	−0.001 (2)	0.025 (2)
C10	0.0368 (19)	0.089 (3)	0.083 (3)	0.0077 (17)	0.0013 (17)	−0.012 (2)
C11	0.0350 (19)	0.093 (3)	0.081 (3)	−0.0156 (17)	0.0181 (19)	−0.015 (2)
C12	0.0417 (19)	0.0643 (19)	0.061 (2)	−0.0119 (13)	0.0216 (16)	0.0033 (14)
C13	0.0291 (13)	0.0446 (13)	0.0366 (15)	0.0046 (10)	0.0116 (11)	0.0011 (11)
C14	0.0353 (16)	0.0481 (15)	0.0427 (18)	0.0018 (11)	0.0117 (13)	−0.0002 (11)
C15	0.053 (2)	0.074 (2)	0.054 (2)	−0.0036 (14)	0.0244 (18)	−0.0152 (15)
C16	0.076 (2)	0.070 (2)	0.049 (2)	0.0112 (18)	0.0221 (17)	−0.0105 (15)
C17	0.091 (3)	0.0550 (18)	0.054 (2)	−0.0113 (18)	0.0199 (19)	−0.0155 (15)

Br1—C2	1.897 (3)	C7—C8	1.372 (4)
O1—C14	1.355 (3)	C7—C12	1.377 (4)
O1—C17	1.378 (4)	C8—C9	1.387 (5)
N1—C5	1.317 (3)	C8—H8	0.93
N1—C1	1.337 (3)	C9—C10	1.362 (5)
N2—C5	1.383 (3)	C9—H9	0.93
N2—C13	1.388 (3)	C10—C11	1.351 (5)
N2—C6	1.462 (3)	C10—H10	0.93
N3—C13	1.324 (3)	C11—C12	1.385 (5)
N3—C4	1.382 (4)	C11—H11	0.93
C1—C2	1.388 (4)	C12—H12	0.93
C1—H1	0.93	C13—C14	1.444 (4)
C2—C3	1.382 (4)	C14—C15	1.341 (5)
C3—C4	1.376 (4)	C15—C16	1.412 (4)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.408 (4)	C16—C17	1.317 (5)
C6—C7	1.505 (4)	C16—H16	0.93
C6—H6A	0.97	C17—H17	0.93
C6—H6B	0.97
C14—O1—C17	105.2 (2)	C7—C8—C9	120.7 (3)
C5—N1—C1	113.9 (2)	C7—C8—H8	119.7
C5—N2—C13	105.62 (19)	C9—C8—H8	119.7
C5—N2—C6	123.9 (2)	C10—C9—C8	120.3 (4)
C13—N2—C6	130.5 (2)	C10—C9—H9	119.8
C13—N3—C4	105.2 (2)	C8—C9—H9	119.8
N1—C1—C2	123.4 (3)	C11—C10—C9	119.6 (3)
N1—C1—H1	118.3	C11—C10—H10	120.2
C2—C1—H1	118.3	C9—C10—H10	120.2
C3—C2—C1	122.2 (2)	C10—C11—C12	120.6 (3)
C3—C2—Br1	119.38 (19)	C10—C11—H11	119.7
C1—C2—Br1	118.46 (19)	C12—C11—H11	119.7
C4—C3—C2	115.2 (2)	C7—C12—C11	120.6 (3)
C4—C3—H3	122.4	C7—C12—H12	119.7
C2—C3—H3	122.4	C11—C12—H12	119.7
C3—C4—N3	131.8 (2)	N3—C13—N2	113.1 (2)
C3—C4—C5	118.4 (3)	N3—C13—C14	121.1 (2)
N3—C4—C5	109.9 (2)	N2—C13—C14	125.8 (2)
N1—C5—N2	126.8 (2)	C15—C14—O1	110.5 (3)
N1—C5—C4	127.0 (2)	C15—C14—C13	129.1 (3)
N2—C5—C4	106.2 (2)	O1—C14—C13	120.3 (3)
N2—C6—C7	114.5 (2)	C14—C15—C16	106.7 (3)
N2—C6—H6A	108.6	C14—C15—H15	126.6
C7—C6—H6A	108.6	C16—C15—H15	126.6
N2—C6—H6B	108.6	C17—C16—C15	106.4 (3)
C7—C6—H6B	108.6	C17—C16—H16	126.8
H6A—C6—H6B	107.6	C15—C16—H16	126.8
C8—C7—C12	118.1 (3)	C16—C17—O1	111.2 (3)
C8—C7—C6	123.2 (2)	C16—C17—H17	124.4
C12—C7—C6	118.6 (2)	O1—C17—H17	124.4
C5—N1—C1—C2	0.0 (4)	C6—C7—C8—C9	−180.0 (3)
N1—C1—C2—C3	0.2 (4)	C7—C8—C9—C10	1.4 (7)
N1—C1—C2—Br1	−179.2 (2)	C8—C9—C10—C11	0.7 (7)
C1—C2—C3—C4	−0.8 (4)	C9—C10—C11—C12	−1.7 (6)
Br1—C2—C3—C4	178.56 (19)	C8—C7—C12—C11	1.3 (5)
C2—C3—C4—N3	−179.3 (3)	C6—C7—C12—C11	179.1 (3)
C2—C3—C4—C5	1.2 (4)	C10—C11—C12—C7	0.7 (6)
C13—N3—C4—C3	179.7 (3)	C4—N3—C13—N2	0.5 (3)
C13—N3—C4—C5	−0.7 (3)	C4—N3—C13—C14	179.9 (2)
C1—N1—C5—N2	178.7 (2)	C5—N2—C13—N3	0.0 (3)
C1—N1—C5—C4	0.4 (4)	C6—N2—C13—N3	179.7 (2)
C13—N2—C5—N1	−179.0 (2)	C5—N2—C13—C14	−179.4 (2)
C6—N2—C5—N1	1.3 (4)	C6—N2—C13—C14	0.3 (4)
C13—N2—C5—C4	−0.4 (3)	C17—O1—C14—C15	0.7 (4)
C6—N2—C5—C4	179.9 (2)	C17—O1—C14—C13	179.1 (3)
C3—C4—C5—N1	−1.1 (4)	N3—C13—C14—C15	1.2 (5)
N3—C4—C5—N1	179.3 (2)	N2—C13—C14—C15	−179.5 (3)
C3—C4—C5—N2	−179.7 (2)	N3—C13—C14—O1	−176.9 (2)
N3—C4—C5—N2	0.7 (3)	N2—C13—C14—O1	2.4 (4)
C5—N2—C6—C7	96.8 (3)	O1—C14—C15—C16	−0.3 (4)
C13—N2—C6—C7	−82.8 (3)	C13—C14—C15—C16	−178.5 (3)
N2—C6—C7—C8	−7.5 (4)	C14—C15—C16—C17	−0.3 (4)
N2—C6—C7—C12	174.8 (2)	C15—C16—C17—O1	0.7 (4)
C12—C7—C8—C9	−2.3 (5)	C14—O1—C17—C16	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3i	0.93	2.51	3.399 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N3i	0.93	2.51	3.399 (4)	160

Symmetry code: (i) .