1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chloro-phen-yl)urea.

In the title compound, C14H11Cl2N5O, the plane of the 1H-imidazo[4,5-c]pyridine ring system [r.m.s. deviation = 0.087 (19) Å] makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring. An intra-molecular N-H⋯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers. These dimers are connected by π-π inter-actions between imidazole rings [shortest centroid-centroid distance = 3.4443 (14) Å].

Related literature

For biological applications of imidazo­pyridines, see: Cappelli et al. (2006 ▶); Weier et al. (1994 ▶); Barraclough et al. (1990 ▶); Bavetsias et al. (2007 ▶); Cooper et al. (1992 ▶); Temple et al. (1987 ▶); Janssens et al. (1985 ▶); Kulkarni & Newman (2007 ▶). For a related structure, see: Kandri Rodi et al. (2013 ▶).

Experimental

Crystal data

C14H11Cl2N5O

M = 336.18

Monoclinic,

a = 8.9368 (3) Å

b = 17.2369 (4) Å

c = 10.3805 (3) Å

β = 114.216 (4)°

V = 1458.33 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 293 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.770, T max = 1.000

11425 measured reflections

2576 independent reflections

2175 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.06

2576 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814000695/bt6956sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000695/bt6956Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000695/bt6956Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H11Cl2N5O	F(000) = 688
Mr = 336.18	Dx = 1.531 Mg m−3
Monoclinic, P21/c	Melting point: 380 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9368 (3) Å	Cell parameters from 2576 reflections
b = 17.2369 (4) Å	θ = 2.4–25.0°
c = 10.3805 (3) Å	µ = 0.45 mm−1
β = 114.216 (4)°	T = 293 K
V = 1458.33 (7) Å3	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	2576 independent reflections
Radiation source: fine-focus sealed tube	2175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
Tmin = 0.770, Tmax = 1.000	k = −20→20
11425 measured reflections	l = −12→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.5893P] where P = (Fo2 + 2Fc2)/3
2576 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. IR cm-1 (KBr) 3431, 1669; Anal. Calcd for C14H11Cl2N5O C,50.02; H, 3.30; N, 20.83%; Found, C, 49.45; H, 3.25; N, 20.44%.

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
Cl1	0.98140 (8)	0.21079 (4)	0.85698 (7)	0.0611 (2)
Cl2	1.28185 (8)	0.14285 (4)	1.18265 (7)	0.0693 (2)
O3	0.50876 (19)	0.04206 (11)	0.86633 (16)	0.0599 (5)
N4	1.1433 (2)	−0.06979 (11)	1.47101 (19)	0.0457 (5)
N5	0.8783 (2)	−0.07679 (11)	1.31848 (19)	0.0474 (5)
N6	1.0050 (2)	0.07252 (10)	1.12745 (18)	0.0424 (4)
N7	0.7418 (2)	0.01864 (11)	1.05733 (18)	0.0447 (5)
H7	0.6847	−0.0136	1.0818	0.054*
N8	0.7379 (2)	0.10758 (10)	0.88673 (17)	0.0389 (4)
H8	0.8420	0.1107	0.9357	0.047*
C9	1.2941 (3)	−0.08685 (16)	1.5946 (2)	0.0587 (6)
H9A	1.3816	−0.0553	1.5925	0.088*
H9B	1.3215	−0.1406	1.5937	0.088*
H9C	1.2783	−0.0758	1.6789	0.088*
C10	0.9933 (3)	−0.10224 (14)	1.4362 (2)	0.0502 (6)
H10	0.9738	−0.1398	1.4919	0.060*
C11	0.9608 (3)	−0.02290 (12)	1.2725 (2)	0.0386 (5)
C12	0.9041 (2)	0.02356 (12)	1.1512 (2)	0.0379 (5)
C13	1.1616 (3)	0.07603 (13)	1.2225 (2)	0.0451 (5)
C14	1.2320 (3)	0.03333 (13)	1.3434 (2)	0.0461 (5)
H14	1.3418	0.0380	1.4053	0.055*
C15	1.1242 (3)	−0.01774 (12)	1.3656 (2)	0.0397 (5)
C16	0.6546 (3)	0.05620 (13)	0.9311 (2)	0.0408 (5)
C17	0.6706 (3)	0.15605 (11)	0.7687 (2)	0.0389 (5)
C18	0.5051 (3)	0.15738 (14)	0.6761 (2)	0.0472 (5)
H18	0.4318	0.1235	0.6897	0.057*
C19	0.4496 (3)	0.20893 (14)	0.5640 (3)	0.0545 (6)
H19	0.3389	0.2093	0.5032	0.065*
C20	0.5541 (4)	0.25923 (15)	0.5406 (3)	0.0621 (7)
H20	0.5148	0.2933	0.4646	0.075*
C21	0.7172 (4)	0.25902 (14)	0.6304 (3)	0.0599 (7)
H21	0.7893	0.2929	0.6152	0.072*
C22	0.7742 (3)	0.20852 (12)	0.7430 (2)	0.0444 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0526 (4)	0.0597 (4)	0.0696 (4)	−0.0158 (3)	0.0237 (3)	−0.0005 (3)
Cl2	0.0440 (4)	0.0822 (5)	0.0688 (4)	−0.0224 (3)	0.0101 (3)	0.0153 (3)
O3	0.0347 (9)	0.0818 (12)	0.0484 (9)	−0.0163 (8)	0.0022 (7)	0.0204 (8)
N4	0.0397 (10)	0.0505 (11)	0.0404 (10)	0.0087 (8)	0.0100 (8)	0.0054 (8)
N5	0.0400 (10)	0.0526 (11)	0.0467 (11)	0.0006 (9)	0.0147 (9)	0.0106 (9)
N6	0.0363 (10)	0.0455 (10)	0.0408 (10)	−0.0063 (8)	0.0112 (8)	−0.0004 (8)
N7	0.0341 (10)	0.0529 (11)	0.0387 (10)	−0.0093 (8)	0.0065 (8)	0.0110 (8)
N8	0.0336 (9)	0.0449 (10)	0.0351 (9)	−0.0055 (8)	0.0111 (7)	0.0019 (8)
C9	0.0453 (14)	0.0688 (16)	0.0477 (14)	0.0113 (12)	0.0047 (11)	0.0098 (12)
C10	0.0472 (13)	0.0525 (13)	0.0499 (13)	0.0054 (11)	0.0188 (11)	0.0130 (11)
C11	0.0343 (11)	0.0416 (11)	0.0379 (11)	0.0012 (9)	0.0126 (9)	0.0003 (9)
C12	0.0327 (11)	0.0422 (11)	0.0362 (11)	−0.0005 (9)	0.0114 (9)	−0.0016 (9)
C13	0.0357 (11)	0.0494 (13)	0.0465 (12)	−0.0066 (10)	0.0131 (10)	−0.0024 (10)
C14	0.0315 (11)	0.0536 (13)	0.0450 (12)	−0.0006 (10)	0.0074 (10)	−0.0022 (10)
C15	0.0378 (11)	0.0415 (11)	0.0365 (11)	0.0041 (9)	0.0119 (9)	−0.0026 (9)
C16	0.0363 (12)	0.0457 (12)	0.0363 (11)	−0.0043 (9)	0.0108 (9)	0.0019 (9)
C17	0.0470 (12)	0.0365 (11)	0.0353 (10)	−0.0009 (9)	0.0191 (10)	−0.0032 (9)
C18	0.0472 (13)	0.0524 (13)	0.0402 (12)	−0.0004 (11)	0.0162 (10)	0.0034 (10)
C19	0.0591 (15)	0.0563 (15)	0.0422 (13)	0.0083 (12)	0.0146 (12)	0.0050 (11)
C20	0.084 (2)	0.0523 (14)	0.0493 (14)	0.0061 (14)	0.0261 (14)	0.0143 (12)
C21	0.0801 (19)	0.0470 (14)	0.0592 (16)	−0.0078 (13)	0.0351 (15)	0.0056 (12)
C22	0.0544 (14)	0.0394 (11)	0.0433 (12)	−0.0050 (10)	0.0239 (11)	−0.0041 (9)

Cl1—C22	1.741 (2)	C9—H9C	0.9600
Cl2—C13	1.737 (2)	C10—H10	0.9300
O3—C16	1.221 (2)	C11—C15	1.384 (3)
N4—C10	1.357 (3)	C11—C12	1.399 (3)
N4—C15	1.371 (3)	C13—C14	1.366 (3)
N4—C9	1.460 (3)	C14—C15	1.391 (3)
N5—C10	1.309 (3)	C14—H14	0.9300
N5—C11	1.387 (3)	C17—C18	1.395 (3)
N6—C12	1.330 (3)	C17—C22	1.396 (3)
N6—C13	1.343 (3)	C18—C19	1.384 (3)
N7—C12	1.379 (3)	C18—H18	0.9300
N7—C16	1.381 (3)	C19—C20	1.366 (4)
N7—H7	0.8600	C19—H19	0.9300
N8—C16	1.353 (3)	C20—C21	1.371 (4)
N8—C17	1.399 (3)	C20—H20	0.9300
N8—H8	0.8600	C21—C22	1.377 (3)
C9—H9A	0.9600	C21—H21	0.9300
C9—H9B	0.9600
C10—N4—C15	105.76 (18)	C14—C13—Cl2	118.66 (17)
C10—N4—C9	127.3 (2)	C13—C14—C15	113.8 (2)
C15—N4—C9	127.0 (2)	C13—C14—H14	123.1
C10—N5—C11	102.76 (18)	C15—C14—H14	123.1
C12—N6—C13	118.28 (18)	N4—C15—C11	105.38 (18)
C12—N7—C16	131.50 (18)	N4—C15—C14	132.7 (2)
C12—N7—H7	114.3	C11—C15—C14	121.92 (19)
C16—N7—H7	114.3	O3—C16—N8	123.74 (19)
C16—N8—C17	126.16 (18)	O3—C16—N7	119.21 (19)
C16—N8—H8	116.9	N8—C16—N7	117.06 (18)
C17—N8—H8	116.9	C18—C17—C22	117.2 (2)
N4—C9—H9A	109.5	C18—C17—N8	124.54 (19)
N4—C9—H9B	109.5	C22—C17—N8	118.3 (2)
H9A—C9—H9B	109.5	C19—C18—C17	120.2 (2)
N4—C9—H9C	109.5	C19—C18—H18	119.9
H9A—C9—H9C	109.5	C17—C18—H18	119.9
H9B—C9—H9C	109.5	C20—C19—C18	121.4 (3)
N5—C10—N4	115.0 (2)	C20—C19—H19	119.3
N5—C10—H10	122.5	C18—C19—H19	119.3
N4—C10—H10	122.5	C19—C20—C21	119.4 (2)
C15—C11—N5	111.13 (18)	C19—C20—H20	120.3
C15—C11—C12	118.69 (19)	C21—C20—H20	120.3
N5—C11—C12	130.18 (19)	C20—C21—C22	119.9 (2)
N6—C12—N7	120.29 (18)	C20—C21—H21	120.0
N6—C12—C11	120.47 (19)	C22—C21—H21	120.0
N7—C12—C11	119.24 (18)	C21—C22—C17	121.9 (2)
N6—C13—C14	126.8 (2)	C21—C22—Cl1	118.86 (18)
N6—C13—Cl2	114.53 (16)	C17—C22—Cl1	119.23 (17)
C11—N5—C10—N4	0.0 (3)	C12—C11—C15—N4	−179.29 (18)
C15—N4—C10—N5	0.2 (3)	N5—C11—C15—C14	−179.01 (19)
C9—N4—C10—N5	−179.6 (2)	C12—C11—C15—C14	1.4 (3)
C10—N5—C11—C15	−0.2 (2)	C13—C14—C15—N4	−179.8 (2)
C10—N5—C11—C12	179.3 (2)	C13—C14—C15—C11	−0.7 (3)
C13—N6—C12—N7	179.27 (19)	C17—N8—C16—O3	5.1 (3)
C13—N6—C12—C11	0.0 (3)	C17—N8—C16—N7	−174.47 (18)
C16—N7—C12—N6	1.5 (4)	C12—N7—C16—O3	−179.5 (2)
C16—N7—C12—C11	−179.2 (2)	C12—N7—C16—N8	0.1 (4)
C15—C11—C12—N6	−1.1 (3)	C16—N8—C17—C18	−1.4 (3)
N5—C11—C12—N6	179.5 (2)	C16—N8—C17—C22	176.71 (19)
C15—C11—C12—N7	179.66 (19)	C22—C17—C18—C19	0.3 (3)
N5—C11—C12—N7	0.2 (3)	N8—C17—C18—C19	178.4 (2)
C12—N6—C13—C14	0.8 (4)	C17—C18—C19—C20	0.2 (4)
C12—N6—C13—Cl2	−179.04 (15)	C18—C19—C20—C21	−0.3 (4)
N6—C13—C14—C15	−0.5 (3)	C19—C20—C21—C22	−0.2 (4)
Cl2—C13—C14—C15	179.40 (16)	C20—C21—C22—C17	0.8 (4)
C10—N4—C15—C11	−0.3 (2)	C20—C21—C22—Cl1	−178.9 (2)
C9—N4—C15—C11	179.5 (2)	C18—C17—C22—C21	−0.8 (3)
C10—N4—C15—C14	178.9 (2)	N8—C17—C22—C21	−179.0 (2)
C9—N4—C15—C14	−1.3 (4)	C18—C17—C22—Cl1	178.84 (16)
N5—C11—C15—N4	0.3 (2)	N8—C17—C22—Cl1	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O3i	0.86	2.07	2.862 (3)	153
N8—H8···N6	0.86	2.03	2.723 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O3i	0.86	2.07	2.862 (3)	153
N8—H8⋯N6	0.86	2.03	2.723 (2)	136

Symmetry code: (i) .