organic compounds
1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea
aP. G. Department of Physics, LVD College, Raichur 584 103, Karnataka, India, bDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India, cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India, and dDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com
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 intramolecular N—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, N—H⋯O hydrogen bonds link the molecules into inversion dimers. These dimers are connected by π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å].
CCDC reference: 981048
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
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Data collection: SMART (Bruker, 2001); cell 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.
Supporting information
CCDC reference: 981048
10.1107/S1600536814000695/bt6956sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000695/bt6956Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000695/bt6956Isup3.cml
A mixture of 2,4,6-trichloropyridene, methylamine in ethanol was heated and filtered to get pure product. To this sulfuric acid and fuming nitric acid was added, then it was stirred and cooled. A solution of iron powder and ammonium chloride in methanol/water was added and heated. Then triethylorthoformate in ethanol was added and continued the heating. Amination of reaction product was achieved by adding benzophenone imine, potassium carbonate, palladium complex, in dioxane, and then it was heated. The obtained product was dissolved in HCl, stirred, and concentrated in vacuo to give the product. A mixture of obtained product, sodium hydride, 6-chloro-1-methyl-1H-imidazol [4,5-c]pyridin-4-amine and carbonyl/sulfonyl chlorides in tetahydrofuran was stirred and concentrated in vacuo to give the expected products. After completion of each step of the reaction TLC was monitored. The compound is recrystallized by ethanol- chloroform mixture. Colourless needles of the title compound were grown from a mixed solution of Ethanol/Chloroform (V/V = 2/1) by slow evaporation at room temperature. Yield: 122 mg, 66.27%; m p: 380; 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%.
All H atoms were positioned geometrically; N—H = 0.86 Å, C—H = 0.93 Å for aromatic H, and C—H = 0.96 Å for methyl H, and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.
The identification of chemotherapeutic targets could lead to new therapeutic approaches and may be a key for the discovery of really effective drugs. The imidazopyridine (Cappelli et al., 2006; Weier et al., 1994; Barraclough et al., 1990; Bavetsias et al., 2007) moieties are important pharmacophores, which have proven to be useful for a number of biologically relevant targets. The compounds derived from the imidazopyridine system have recently been evaluated as antagonists of various biological receptors, including angiotensin-II and platelet activating factor (Cooper et al., 1992). Substituted imidazo[4,5]pyridines have also been tested for their potential as anticancer (Temple et al., 1987) and selective antihistamine (H1) agents (Janssens et al., 1985). Imidazo[4,5]pyridine derivatives were also reported as inhibitors of Mitogen and stress-activated protein kinases and Aurora kinases (Kulkarni & Newman, 2007). The bond lengths and bond angles are good agreement with a related structure (Kandri Rodi et al., 2013)
The
of 1-(6-chloro-1-methyl-1H-imidazo [4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea is shown in Fig. 1. The 1H-imidazo[4,5-c]pyridine ring (N4/N5/N6/C10–C15) system makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring.An intramolecular N-H···N hydrogen bond stabilizes the π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å]. A view of the crystal packing is given in Figure 2.
Intermolecular N-H···O hydrogen bonds link the molecules to centrosymmetric dimers. These dimers are further connected by intermolecularFor biological applications of imidazopyridine, 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).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).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 |
C14H11Cl2N5O | V = 1458.33 (7) Å3 |
Mr = 336.18 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.9368 (3) Å | µ = 0.45 mm−1 |
b = 17.2369 (4) Å | T = 293 K |
c = 10.3805 (3) Å | 0.24 × 0.20 × 0.12 mm |
β = 114.216 (4)° |
Bruker SMART CCD area-detector diffractometer | 2576 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 2175 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 1.000 | Rint = 0.023 |
11425 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.38 e Å−3 |
2576 reflections | Δρmin = −0.28 e Å−3 |
199 parameters |
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 |
Symmetry code: (i) −x+1, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O3i | 0.86 | 2.0700 | 2.862 (3) | 153 |
N8—H8···N6 | 0.86 | 2.0300 | 2.723 (2) | 136 |
Symmetry code: (i) −x+1, −y, −z+2. |
Acknowledgements
VBD acknowledges the VGST (Vision Group of Science & Technology, Department. IT, BT and S & T, Govt. of Karnataka) for financial support (No. VGST/P-15/K-FIST Level-1 /2010–11/744 dated 21/03/2011).
References
Barraclough, P., Black, J. W., Cambridge, D., Collard, D., Firmin, D., Gerskowitch, V. P., Glen, R. C., Giles, H., Hill, A. P., Hull, R. A. D., Iyer, R., King, W. R., Kneen, C. O., Lindon, J. C., Nobbs, M. S., Randall, P., Shah, G. P., Smith, S., Vine, S. J., Whiting, M. V. & Williams, J. M. (1990). J. Med. Chem. 33, 2231–2239. CrossRef CAS PubMed Web of Science Google Scholar
Bavetsias, V., Sun, C., Bouloc, N., Reynisson, J., Workman, P., Linardopoulos, S. & McDonald, E. (2007). Bioorg. Med. Chem. 17, 6567–6571. Web of Science CrossRef CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Cappelli, A., Mohr, G. P., Giuliani, G., Galeazzi, S., Anzini, M., Mennuni, L., Ferrari, F., Macoves, F., Krienrath, E. M., Langer, T., Valoti, M., Giorgi, G. & Vomero, S. (2006). J. Med. Chem. 49, 6451–6464. Web of Science CSD CrossRef PubMed CAS Google Scholar
Cooper, K., Fray, M. J., Parry, J. M., Richardson, K. & Steele, J. (1992). J. Med. Chem. 35, 3115–3120. CrossRef PubMed CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943–1947. CrossRef CAS PubMed Web of Science Google Scholar
Kandri Rodi, Y., Haoudi, A., Capet, F., Mazzah, A., Essassi, E. M. & El Ammari, L. (2013). Acta Cryst. E69, o1029–o1030. CSD CrossRef CAS IUCr Journals Google Scholar
Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987–2991. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Temple, J. C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746–1751. CrossRef CAS PubMed Web of Science Google Scholar
Weier, R. M., Khanna, I. K., Lentz, K., Stealey, M. A. & Julien, J. (1994). (Searle) US Patent No. 5359073. Google Scholar
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The identification of chemotherapeutic targets could lead to new therapeutic approaches and may be a key for the discovery of really effective drugs. The imidazopyridine (Cappelli et al., 2006; Weier et al., 1994; Barraclough et al., 1990; Bavetsias et al., 2007) moieties are important pharmacophores, which have proven to be useful for a number of biologically relevant targets. The compounds derived from the imidazopyridine system have recently been evaluated as antagonists of various biological receptors, including angiotensin-II and platelet activating factor (Cooper et al., 1992). Substituted imidazo[4,5]pyridines have also been tested for their potential as anticancer (Temple et al., 1987) and selective antihistamine (H1) agents (Janssens et al., 1985). Imidazo[4,5]pyridine derivatives were also reported as inhibitors of Mitogen and stress-activated protein kinases and Aurora kinases (Kulkarni & Newman, 2007). The bond lengths and bond angles are good agreement with a related structure (Kandri Rodi et al., 2013)
The asymmetric unit of 1-(6-chloro-1-methyl-1H-imidazo [4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea is shown in Fig. 1. The 1H-imidazo[4,5-c]pyridine ring (N4/N5/N6/C10–C15) system makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring.
An intramolecular N-H···N hydrogen bond stabilizes the molecular conformation. Intermolecular N-H···O hydrogen bonds link the molecules to centrosymmetric dimers. These dimers are further connected by intermolecular π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å]. A view of the crystal packing is given in Figure 2.