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

The imidazopyridine fused ring in the title compound, C(19)H(14)BrN(3), is almost coplanar with the phenyl ring at the 2-position of the five-membered ring [dihedral angle = 2.4 (1). The crystal structure features short Br⋯Br contacts [3.562 (1) Å].

Related literature

For the synthesis of imidazo[4,5-b]pyridines, see: Aridoss et al. (2006 ▶); Benham et al. (1995 ▶); Cundy et al. (1997 ▶); Kale et al. (2009 ▶); Walsh et al. (1994 ▶); Zaki & Proença (2007 ▶).

Experimental

Crystal data

C19H14BrN3

M = 364.24

Monoclinic,

a = 8.6613 (6) Å

b = 19.7631 (13) Å

c = 9.3683 (6) Å

β = 99.647 (3)°

V = 1580.93 (18) Å3

Z = 4

Mo Kα radiation

μ = 2.60 mm−1

T = 293 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.529, T max = 0.624

57936 measured reflections

4613 independent reflections

3492 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.098

S = 1.00

4613 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.51 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/S160053681001038X/pk2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001038X/pk2232Isup2.hkl

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

C19H14BrN3	F(000) = 736
Mr = 364.24	Dx = 1.530 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9876 reflections
a = 8.6613 (6) Å	θ = 2.4–27.2°
b = 19.7631 (13) Å	µ = 2.60 mm−1
c = 9.3683 (6) Å	T = 293 K
β = 99.647 (3)°	Prism, brown
V = 1580.93 (18) Å3	0.28 × 0.24 × 0.20 mm
Z = 4

Bruker X8 APEXII diffractometer	4613 independent reflections
Radiation source: fine-focus sealed tube	3492 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.529, Tmax = 0.624	k = −27→27
57936 measured reflections	l = −13→13

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.5269P] where P = (Fo2 + 2Fc2)/3
4613 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.10158 (3)	0.475089 (12)	0.85824 (2)	0.06483 (10)
N1	0.29485 (16)	0.43405 (7)	0.49901 (15)	0.0385 (3)
N2	0.26154 (17)	0.60722 (7)	0.40338 (16)	0.0424 (3)
N3	0.35446 (17)	0.50867 (7)	0.31224 (15)	0.0387 (3)
C1	0.1792 (2)	0.48667 (9)	0.68312 (19)	0.0454 (4)
C2	0.1807 (2)	0.55060 (9)	0.62007 (19)	0.0458 (4)
H2	0.1429	0.5886	0.6616	0.055*
C3	0.2408 (2)	0.55460 (8)	0.49376 (18)	0.0392 (3)
C4	0.29944 (19)	0.49489 (8)	0.43321 (17)	0.0367 (3)
C5	0.2352 (2)	0.43003 (9)	0.62362 (18)	0.0437 (4)
H5	0.2322	0.3884	0.6694	0.052*
C6	0.32810 (19)	0.57716 (8)	0.30027 (17)	0.0379 (3)
C7	0.37246 (19)	0.61435 (8)	0.17772 (18)	0.0390 (3)
C8	0.3423 (2)	0.68335 (9)	0.1595 (2)	0.0459 (4)
H8	0.2938	0.7067	0.2261	0.055*
C9	0.3845 (2)	0.71728 (10)	0.0425 (2)	0.0547 (5)
H9	0.3644	0.7634	0.0310	0.066*
C10	0.4557 (3)	0.68322 (11)	−0.0569 (2)	0.0574 (5)
H10	0.4829	0.7062	−0.1357	0.069*
C11	0.4869 (3)	0.61517 (11)	−0.0399 (2)	0.0624 (5)
H11	0.5353	0.5922	−0.1069	0.075*
C12	0.4459 (3)	0.58097 (10)	0.0773 (2)	0.0538 (5)
H12	0.4679	0.5350	0.0888	0.065*
C13	0.3544 (2)	0.37271 (8)	0.43491 (19)	0.0427 (3)
H13A	0.4041	0.3433	0.5121	0.051*
H13B	0.4331	0.3859	0.3778	0.051*
C14	0.22599 (19)	0.33413 (8)	0.34017 (17)	0.0380 (3)
C15	0.1392 (2)	0.36407 (9)	0.21824 (19)	0.0481 (4)
H15	0.1605	0.4084	0.1945	0.058*
C16	0.0214 (3)	0.32854 (11)	0.1321 (2)	0.0574 (5)
H16	−0.0379	0.3494	0.0522	0.069*
C17	−0.0082 (3)	0.26217 (11)	0.1643 (2)	0.0585 (5)
H17	−0.0859	0.2380	0.1050	0.070*
C18	0.0769 (3)	0.23206 (10)	0.2833 (3)	0.0598 (5)
H18	0.0570	0.1873	0.3047	0.072*
C19	0.1930 (2)	0.26789 (9)	0.3728 (2)	0.0517 (4)
H19	0.2487	0.2473	0.4548	0.062*

	U11	U22	U33	U12	U13	U23
Br1	0.08695 (19)	0.06436 (15)	0.05128 (13)	0.00593 (10)	0.03507 (11)	0.00630 (9)
N1	0.0419 (7)	0.0355 (6)	0.0382 (7)	0.0001 (5)	0.0074 (5)	0.0003 (5)
N2	0.0515 (8)	0.0338 (6)	0.0437 (7)	−0.0007 (6)	0.0131 (6)	−0.0028 (5)
N3	0.0443 (7)	0.0337 (6)	0.0394 (7)	−0.0009 (5)	0.0104 (5)	−0.0012 (5)
C1	0.0501 (10)	0.0498 (10)	0.0386 (8)	−0.0024 (7)	0.0140 (7)	0.0004 (7)
C2	0.0535 (10)	0.0417 (9)	0.0444 (9)	−0.0007 (7)	0.0147 (7)	−0.0056 (7)
C3	0.0431 (8)	0.0349 (7)	0.0402 (8)	−0.0015 (6)	0.0088 (6)	−0.0046 (6)
C4	0.0390 (8)	0.0345 (7)	0.0366 (7)	−0.0020 (6)	0.0061 (6)	−0.0035 (6)
C5	0.0485 (9)	0.0430 (8)	0.0403 (8)	−0.0019 (7)	0.0094 (7)	0.0036 (7)
C6	0.0407 (8)	0.0345 (7)	0.0385 (7)	−0.0028 (6)	0.0068 (6)	−0.0023 (6)
C7	0.0420 (8)	0.0353 (7)	0.0395 (7)	−0.0036 (6)	0.0064 (6)	−0.0004 (6)
C8	0.0471 (9)	0.0360 (8)	0.0553 (10)	−0.0020 (7)	0.0105 (8)	−0.0007 (7)
C9	0.0567 (11)	0.0391 (9)	0.0678 (12)	−0.0031 (8)	0.0092 (9)	0.0118 (8)
C10	0.0647 (12)	0.0560 (11)	0.0530 (10)	−0.0070 (9)	0.0141 (9)	0.0153 (9)
C11	0.0851 (15)	0.0567 (12)	0.0516 (10)	0.0037 (11)	0.0298 (10)	0.0062 (9)
C12	0.0782 (13)	0.0393 (9)	0.0486 (10)	0.0062 (9)	0.0240 (9)	0.0040 (7)
C13	0.0430 (9)	0.0371 (8)	0.0483 (9)	0.0064 (7)	0.0091 (7)	0.0015 (7)
C14	0.0419 (8)	0.0331 (7)	0.0416 (8)	0.0029 (6)	0.0147 (6)	−0.0002 (6)
C15	0.0608 (11)	0.0390 (8)	0.0446 (9)	−0.0013 (8)	0.0092 (8)	0.0021 (7)
C16	0.0660 (12)	0.0574 (11)	0.0462 (10)	−0.0037 (9)	0.0015 (9)	−0.0030 (8)
C17	0.0603 (12)	0.0584 (12)	0.0587 (11)	−0.0140 (9)	0.0152 (9)	−0.0156 (9)
C18	0.0683 (13)	0.0396 (9)	0.0754 (14)	−0.0103 (9)	0.0233 (11)	−0.0022 (9)
C19	0.0583 (11)	0.0388 (9)	0.0593 (11)	0.0013 (8)	0.0139 (9)	0.0088 (8)

Br1—C1	1.8882 (18)	C9—H9	0.9300
N1—C4	1.355 (2)	C10—C11	1.376 (3)
N1—C5	1.356 (2)	C10—H10	0.9300
N1—C13	1.483 (2)	C11—C12	1.385 (3)
N2—C6	1.344 (2)	C11—H11	0.9300
N2—C3	1.372 (2)	C12—H12	0.9300
N3—C4	1.329 (2)	C13—C14	1.508 (2)
N3—C6	1.374 (2)	C13—H13A	0.9700
C1—C5	1.375 (3)	C13—H13B	0.9700
C1—C2	1.396 (3)	C14—C19	1.385 (2)
C2—C3	1.373 (2)	C14—C15	1.390 (2)
C2—H2	0.9300	C15—C16	1.382 (3)
C3—C4	1.438 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.379 (3)
C6—C7	1.468 (2)	C16—H16	0.9300
C7—C12	1.388 (3)	C17—C18	1.366 (3)
C7—C8	1.394 (2)	C17—H17	0.9300
C8—C9	1.385 (3)	C18—C19	1.390 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.376 (3)	C19—H19	0.9300
C4—N1—C5	119.22 (14)	C11—C10—H10	120.0
C4—N1—C13	120.17 (14)	C9—C10—H10	120.0
C5—N1—C13	120.61 (14)	C10—C11—C12	119.8 (2)
C6—N2—C3	102.99 (13)	C10—C11—H11	120.1
C4—N3—C6	101.13 (13)	C12—C11—H11	120.1
C5—C1—C2	122.44 (16)	C11—C12—C7	120.86 (18)
C5—C1—Br1	117.06 (13)	C11—C12—H12	119.6
C2—C1—Br1	120.49 (14)	C7—C12—H12	119.6
C3—C2—C1	116.66 (16)	N1—C13—C14	112.30 (13)
C3—C2—H2	121.7	N1—C13—H13A	109.1
C1—C2—H2	121.7	C14—C13—H13A	109.1
N2—C3—C2	133.11 (16)	N1—C13—H13B	109.1
N2—C3—C4	106.70 (14)	C14—C13—H13B	109.1
C2—C3—C4	120.18 (16)	H13A—C13—H13B	107.9
N3—C4—N1	127.72 (15)	C19—C14—C15	118.70 (17)
N3—C4—C3	111.64 (14)	C19—C14—C13	120.47 (16)
N1—C4—C3	120.64 (15)	C15—C14—C13	120.82 (15)
N1—C5—C1	120.85 (16)	C16—C15—C14	120.56 (17)
N1—C5—H5	119.6	C16—C15—H15	119.7
C1—C5—H5	119.6	C14—C15—H15	119.7
N2—C6—N3	117.54 (14)	C17—C16—C15	120.1 (2)
N2—C6—C7	122.76 (14)	C17—C16—H16	119.9
N3—C6—C7	119.70 (14)	C15—C16—H16	119.9
C12—C7—C8	118.69 (17)	C18—C17—C16	119.88 (19)
C12—C7—C6	120.15 (15)	C18—C17—H17	120.1
C8—C7—C6	121.17 (16)	C16—C17—H17	120.1
C9—C8—C7	120.11 (18)	C17—C18—C19	120.47 (18)
C9—C8—H8	119.9	C17—C18—H18	119.8
C7—C8—H8	119.9	C19—C18—H18	119.8
C10—C9—C8	120.42 (18)	C14—C19—C18	120.25 (18)
C10—C9—H9	119.8	C14—C19—H19	119.9
C8—C9—H9	119.8	C18—C19—H19	119.9
C11—C10—C9	120.08 (18)
C5—C1—C2—C3	0.3 (3)	N2—C6—C7—C12	177.72 (18)
Br1—C1—C2—C3	179.25 (13)	N3—C6—C7—C12	−2.4 (2)
C6—N2—C3—C2	179.20 (19)	N2—C6—C7—C8	−2.2 (3)
C6—N2—C3—C4	−0.16 (17)	N3—C6—C7—C8	177.69 (16)
C1—C2—C3—N2	−179.77 (18)	C12—C7—C8—C9	0.4 (3)
C1—C2—C3—C4	−0.5 (3)	C6—C7—C8—C9	−179.61 (16)
C6—N3—C4—N1	−179.97 (16)	C7—C8—C9—C10	0.2 (3)
C6—N3—C4—C3	−0.15 (18)	C8—C9—C10—C11	−0.6 (3)
C5—N1—C4—N3	179.35 (16)	C9—C10—C11—C12	0.2 (4)
C13—N1—C4—N3	−0.7 (3)	C10—C11—C12—C7	0.5 (4)
C5—N1—C4—C3	−0.5 (2)	C8—C7—C12—C11	−0.8 (3)
C13—N1—C4—C3	179.47 (15)	C6—C7—C12—C11	179.25 (19)
N2—C3—C4—N3	0.21 (19)	C4—N1—C13—C14	−94.67 (18)
C2—C3—C4—N3	−179.25 (16)	C5—N1—C13—C14	85.26 (19)
N2—C3—C4—N1	−179.95 (15)	N1—C13—C14—C19	−119.47 (17)
C2—C3—C4—N1	0.6 (2)	N1—C13—C14—C15	60.9 (2)
C4—N1—C5—C1	0.3 (2)	C19—C14—C15—C16	0.5 (3)
C13—N1—C5—C1	−179.68 (16)	C13—C14—C15—C16	−179.83 (17)
C2—C1—C5—N1	−0.2 (3)	C14—C15—C16—C17	−1.8 (3)
Br1—C1—C5—N1	−179.17 (13)	C15—C16—C17—C18	1.4 (3)
C3—N2—C6—N3	0.1 (2)	C16—C17—C18—C19	0.2 (3)
C3—N2—C6—C7	180.00 (15)	C15—C14—C19—C18	1.1 (3)
C4—N3—C6—N2	0.05 (19)	C13—C14—C19—C18	−178.56 (17)
C4—N3—C6—C7	−179.88 (14)	C17—C18—C19—C14	−1.5 (3)