organic compounds
N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)benzenesulfonamide
aP. G. Department of Physics, LVD College, Raichur 584 103, Karnataka, India, bDepartment of Chemistry, Karnatak Science College, Karnatak University, Dharwad, Karnataka 580 001, India, cDepartment of Physics, Moodlakatte Institute of Technology, Kundapura 576 217, 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
The 13H11ClN4O2S, contains two molecules (A and B), in which the dihedral angles between the 1H-imidazo[4,5-c]pyridine system and terminal phenyl ring are 80.83 (10) and 62.34 (1)°. In the crystal, A–B dimers are linked by pairs of N—H⋯N hydrogen bonds, which generate R22(10) loops. The dimers are linked by C—H⋯O and C—H⋯Cl interactions, generating a three-dimensional network. Aromatic π–π stacking interactions [shortest centroid–centroid distance = 3.5211 (12) Å] are also observed.
of the title compound, CCCDC reference: 990803
Related literature
For biological background, see: 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: 990803
10.1107/S1600536814005388/hb7208sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005388/hb7208Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005388/hb7208Isup3.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: 121 mg, 64.84%); mp: 336k; IR cm-1 (KBr) 3435, 1388; Anal. Calcd for C13H11ClN4O2S C, 45.82; H, 2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%.
All H atoms were positioned geometrically, with 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.
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).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as open dashed bonds. |
C13H11ClN4O2S | F(000) = 1328 |
Mr = 322.77 | Dx = 1.518 Mg m−3 |
Monoclinic, P21/c | Melting point: 376 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1045 (4) Å | Cell parameters from 4972 reflections |
b = 14.7259 (5) Å | θ = 2.8–25.0° |
c = 14.6953 (6) Å | µ = 0.43 mm−1 |
β = 95.127 (3)° | T = 293 K |
V = 2824.49 (17) Å3 | Plate, colourless |
Z = 8 | 0.24 × 0.20 × 0.12 mm |
Bruker SMART CCD diffractometer | 4972 independent reflections |
Radiation source: fine-focus sealed tube | 3759 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and ϕ scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→15 |
Tmin = 0.770, Tmax = 1.000 | k = −17→17 |
16038 measured reflections | l = −17→17 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3 |
4972 reflections | (Δ/σ)max = 0.001 |
379 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C13H11ClN4O2S | V = 2824.49 (17) Å3 |
Mr = 322.77 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1045 (4) Å | µ = 0.43 mm−1 |
b = 14.7259 (5) Å | T = 293 K |
c = 14.6953 (6) Å | 0.24 × 0.20 × 0.12 mm |
β = 95.127 (3)° |
Bruker SMART CCD diffractometer | 4972 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3759 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 1.000 | Rint = 0.031 |
16038 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
4972 reflections | Δρmin = −0.31 e Å−3 |
379 parameters |
Experimental. IR cm-1 (KBr) 3435, 1388; Anal. Calcd for C13H11ClN4O2S C, 45.82; H, 2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%. |
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 | ||
Cl1A | 0.20678 (5) | 0.52370 (5) | 0.40718 (5) | 0.06025 (19) | |
Cl1B | 0.93941 (5) | 0.41848 (4) | 0.38570 (5) | 0.05977 (19) | |
S2A | 0.28936 (4) | 0.22270 (3) | 0.58582 (4) | 0.03821 (16) | |
S2B | 0.70463 (4) | 0.13503 (3) | 0.40663 (4) | 0.03622 (15) | |
O3A | 0.26710 (11) | 0.21724 (10) | 0.48964 (11) | 0.0500 (4) | |
O3B | 0.70151 (13) | 0.19837 (10) | 0.47946 (11) | 0.0522 (4) | |
O4A | 0.32556 (11) | 0.14347 (9) | 0.63449 (13) | 0.0562 (5) | |
O4B | 0.63810 (11) | 0.05785 (9) | 0.40271 (11) | 0.0461 (4) | |
N5A | 0.51992 (13) | 0.58429 (10) | 0.64248 (12) | 0.0357 (4) | |
N5B | 0.62508 (13) | 0.45541 (11) | 0.14780 (12) | 0.0369 (4) | |
N6A | 0.30372 (12) | 0.41345 (11) | 0.52175 (12) | 0.0371 (4) | |
N6B | 0.79517 (13) | 0.30202 (11) | 0.33564 (12) | 0.0376 (4) | |
N7A | 0.37871 (13) | 0.29776 (10) | 0.61344 (13) | 0.0439 (5) | |
H7A | 0.4314 | 0.2801 | 0.6480 | 0.053* | |
N7B | 0.67403 (13) | 0.18711 (11) | 0.30975 (12) | 0.0394 (4) | |
H7B | 0.6335 | 0.1599 | 0.2693 | 0.047* | |
N8A | 0.52770 (13) | 0.43954 (10) | 0.69189 (12) | 0.0360 (4) | |
N8B | 0.56595 (12) | 0.31475 (11) | 0.16965 (12) | 0.0364 (4) | |
C9A | 0.17905 (15) | 0.26081 (13) | 0.63400 (15) | 0.0354 (5) | |
C9B | 0.83185 (15) | 0.09728 (13) | 0.40267 (14) | 0.0354 (5) | |
C10A | 0.1679 (2) | 0.23876 (17) | 0.72382 (18) | 0.0609 (7) | |
H10A | 0.2202 | 0.2094 | 0.7593 | 0.073* | |
C10B | 0.91108 (18) | 0.14379 (15) | 0.44983 (16) | 0.0482 (6) | |
H10B | 0.8982 | 0.1949 | 0.4842 | 0.058* | |
C11A | 0.0783 (3) | 0.2610 (2) | 0.7596 (2) | 0.0800 (9) | |
H11A | 0.0695 | 0.2463 | 0.8200 | 0.096* | |
C11B | 1.01033 (19) | 0.11297 (18) | 0.44508 (19) | 0.0594 (7) | |
H11B | 1.0645 | 0.1433 | 0.4771 | 0.071* | |
C12A | 0.0013 (2) | 0.30470 (19) | 0.7073 (2) | 0.0755 (9) | |
H12A | −0.0596 | 0.3187 | 0.7321 | 0.091* | |
C12B | 1.0294 (2) | 0.03867 (19) | 0.39389 (19) | 0.0615 (7) | |
H12B | 1.0964 | 0.0189 | 0.3909 | 0.074* | |
C13A | 0.01382 (19) | 0.32755 (18) | 0.6197 (2) | 0.0641 (7) | |
H13A | −0.0383 | 0.3579 | 0.5849 | 0.077* | |
C13B | 0.9501 (2) | −0.00710 (18) | 0.34674 (18) | 0.0577 (7) | |
H13B | 0.9635 | −0.0576 | 0.3117 | 0.069* | |
C14A | 0.10334 (16) | 0.30612 (15) | 0.58193 (17) | 0.0458 (6) | |
H14A | 0.1122 | 0.3222 | 0.5219 | 0.055* | |
C14B | 0.85071 (18) | 0.02174 (14) | 0.35123 (16) | 0.0458 (6) | |
H14B | 0.7968 | −0.0094 | 0.3198 | 0.055* | |
C15A | 0.37606 (14) | 0.38857 (12) | 0.58513 (14) | 0.0318 (4) | |
C15B | 0.71004 (15) | 0.27352 (12) | 0.28880 (13) | 0.0321 (5) | |
C16A | 0.30231 (16) | 0.50038 (14) | 0.49461 (15) | 0.0378 (5) | |
C16B | 0.82753 (15) | 0.38663 (14) | 0.32074 (14) | 0.0376 (5) | |
C17A | 0.36691 (15) | 0.56812 (13) | 0.52574 (14) | 0.0356 (5) | |
H17A | 0.3617 | 0.6274 | 0.5041 | 0.043* | |
C17B | 0.78186 (16) | 0.44845 (13) | 0.26077 (14) | 0.0367 (5) | |
H17B | 0.8070 | 0.5069 | 0.2538 | 0.044* | |
C18A | 0.44159 (15) | 0.54000 (12) | 0.59313 (13) | 0.0298 (4) | |
C18B | 0.69432 (14) | 0.41563 (13) | 0.21132 (13) | 0.0317 (4) | |
C19A | 0.44741 (14) | 0.45033 (12) | 0.62405 (13) | 0.0290 (4) | |
C19B | 0.65665 (14) | 0.32852 (12) | 0.22385 (13) | 0.0309 (4) | |
C20A | 0.56688 (17) | 0.52153 (13) | 0.69992 (15) | 0.0386 (5) | |
H20A | 0.6223 | 0.5356 | 0.7415 | 0.046* | |
C20B | 0.55180 (16) | 0.39220 (14) | 0.12623 (15) | 0.0401 (5) | |
H20B | 0.4959 | 0.4029 | 0.0840 | 0.048* | |
C21A | 0.54967 (18) | 0.67998 (13) | 0.63396 (16) | 0.0468 (6) | |
H21A | 0.5035 | 0.7092 | 0.5887 | 0.070* | |
H21B | 0.6182 | 0.6833 | 0.6159 | 0.070* | |
H21C | 0.5467 | 0.7099 | 0.6917 | 0.070* | |
C21B | 0.62941 (19) | 0.54775 (14) | 0.11289 (18) | 0.0530 (6) | |
H21D | 0.6901 | 0.5772 | 0.1399 | 0.080* | |
H21E | 0.5700 | 0.5808 | 0.1280 | 0.080* | |
H21F | 0.6310 | 0.5461 | 0.0477 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0494 (4) | 0.0661 (4) | 0.0616 (4) | 0.0194 (3) | −0.0152 (3) | 0.0047 (3) |
Cl1B | 0.0511 (4) | 0.0597 (4) | 0.0645 (4) | −0.0155 (3) | −0.0170 (3) | 0.0071 (3) |
S2A | 0.0297 (3) | 0.0228 (3) | 0.0614 (4) | −0.0001 (2) | −0.0003 (2) | −0.0053 (2) |
S2B | 0.0421 (3) | 0.0276 (3) | 0.0390 (3) | −0.0011 (2) | 0.0037 (2) | 0.0059 (2) |
O3A | 0.0468 (9) | 0.0467 (9) | 0.0569 (11) | −0.0055 (7) | 0.0075 (8) | −0.0219 (7) |
O3B | 0.0701 (11) | 0.0442 (9) | 0.0439 (10) | −0.0004 (8) | 0.0137 (8) | −0.0035 (7) |
O4A | 0.0366 (8) | 0.0248 (7) | 0.1057 (14) | 0.0018 (6) | −0.0022 (9) | 0.0105 (8) |
O4B | 0.0462 (9) | 0.0344 (8) | 0.0572 (10) | −0.0067 (7) | 0.0017 (8) | 0.0130 (7) |
N5A | 0.0416 (10) | 0.0235 (8) | 0.0423 (11) | −0.0050 (7) | 0.0055 (8) | −0.0038 (7) |
N5B | 0.0379 (10) | 0.0332 (9) | 0.0396 (10) | 0.0005 (8) | 0.0031 (8) | 0.0124 (8) |
N6A | 0.0325 (9) | 0.0314 (9) | 0.0467 (11) | 0.0043 (7) | −0.0009 (8) | −0.0028 (8) |
N6B | 0.0372 (10) | 0.0336 (9) | 0.0413 (11) | −0.0010 (8) | −0.0012 (8) | 0.0063 (7) |
N7A | 0.0336 (9) | 0.0254 (9) | 0.0695 (14) | −0.0021 (7) | −0.0125 (9) | 0.0058 (8) |
N7B | 0.0438 (10) | 0.0285 (9) | 0.0437 (11) | −0.0036 (8) | −0.0083 (8) | 0.0071 (7) |
N8A | 0.0404 (10) | 0.0297 (9) | 0.0372 (10) | −0.0031 (7) | 0.0001 (8) | −0.0019 (7) |
N8B | 0.0340 (9) | 0.0362 (9) | 0.0387 (10) | −0.0022 (8) | 0.0012 (8) | 0.0083 (8) |
C9A | 0.0366 (11) | 0.0258 (10) | 0.0434 (13) | −0.0020 (9) | 0.0016 (10) | −0.0051 (9) |
C9B | 0.0400 (11) | 0.0297 (10) | 0.0356 (12) | −0.0018 (9) | −0.0016 (9) | 0.0104 (9) |
C10A | 0.0735 (18) | 0.0581 (15) | 0.0509 (17) | 0.0107 (14) | 0.0045 (14) | 0.0047 (12) |
C10B | 0.0552 (15) | 0.0413 (12) | 0.0451 (14) | −0.0063 (11) | −0.0117 (11) | 0.0010 (10) |
C11A | 0.112 (3) | 0.075 (2) | 0.059 (2) | 0.0138 (19) | 0.0413 (19) | 0.0038 (15) |
C11B | 0.0455 (14) | 0.0673 (17) | 0.0621 (18) | −0.0127 (13) | −0.0139 (12) | 0.0145 (14) |
C12A | 0.070 (2) | 0.0649 (18) | 0.098 (3) | 0.0096 (15) | 0.0439 (19) | −0.0142 (17) |
C12B | 0.0413 (14) | 0.0714 (18) | 0.072 (2) | 0.0066 (13) | 0.0078 (13) | 0.0200 (15) |
C13A | 0.0477 (15) | 0.0657 (17) | 0.080 (2) | 0.0208 (13) | 0.0115 (14) | −0.0072 (15) |
C13B | 0.0556 (16) | 0.0572 (15) | 0.0608 (17) | 0.0078 (13) | 0.0083 (13) | −0.0008 (13) |
C14A | 0.0399 (12) | 0.0465 (13) | 0.0508 (15) | 0.0105 (10) | 0.0024 (11) | −0.0005 (11) |
C14B | 0.0480 (14) | 0.0406 (12) | 0.0478 (14) | −0.0033 (10) | −0.0011 (11) | −0.0016 (10) |
C15A | 0.0319 (10) | 0.0243 (9) | 0.0393 (12) | 0.0022 (8) | 0.0044 (9) | −0.0036 (8) |
C15B | 0.0335 (11) | 0.0271 (10) | 0.0362 (12) | 0.0017 (9) | 0.0061 (9) | 0.0040 (8) |
C16A | 0.0350 (11) | 0.0386 (12) | 0.0394 (13) | 0.0117 (10) | 0.0013 (10) | −0.0018 (9) |
C16B | 0.0346 (11) | 0.0399 (12) | 0.0381 (13) | −0.0043 (9) | 0.0028 (9) | 0.0002 (9) |
C17A | 0.0401 (11) | 0.0287 (10) | 0.0394 (12) | 0.0078 (9) | 0.0106 (10) | 0.0025 (9) |
C17B | 0.0390 (11) | 0.0317 (10) | 0.0400 (13) | −0.0066 (9) | 0.0065 (10) | 0.0053 (9) |
C18A | 0.0345 (11) | 0.0264 (10) | 0.0301 (11) | 0.0021 (8) | 0.0117 (9) | −0.0037 (8) |
C18B | 0.0344 (10) | 0.0299 (10) | 0.0318 (11) | 0.0005 (9) | 0.0092 (9) | 0.0065 (8) |
C19A | 0.0310 (10) | 0.0269 (10) | 0.0297 (11) | 0.0007 (8) | 0.0063 (9) | −0.0019 (8) |
C19B | 0.0306 (10) | 0.0298 (10) | 0.0330 (12) | 0.0012 (8) | 0.0066 (9) | 0.0024 (8) |
C20A | 0.0412 (12) | 0.0351 (11) | 0.0379 (13) | −0.0038 (9) | −0.0044 (10) | −0.0052 (9) |
C20B | 0.0350 (11) | 0.0429 (12) | 0.0412 (13) | −0.0033 (10) | −0.0034 (10) | 0.0116 (10) |
C21A | 0.0570 (14) | 0.0276 (11) | 0.0568 (15) | −0.0101 (10) | 0.0108 (12) | −0.0030 (10) |
C21B | 0.0605 (15) | 0.0373 (12) | 0.0606 (16) | −0.0016 (11) | 0.0013 (13) | 0.0230 (11) |
Cl1A—C16A | 1.746 (2) | C10B—C11B | 1.385 (3) |
Cl1B—C16B | 1.741 (2) | C10B—H10B | 0.9300 |
S2A—O3A | 1.4198 (17) | C11A—C12A | 1.373 (4) |
S2A—O4A | 1.4273 (15) | C11A—H11A | 0.9300 |
S2A—N7A | 1.6347 (17) | C11B—C12B | 1.363 (4) |
S2A—C9A | 1.757 (2) | C11B—H11B | 0.9300 |
S2B—O3B | 1.4230 (16) | C12A—C13A | 1.354 (4) |
S2B—O4B | 1.4305 (14) | C12A—H12A | 0.9300 |
S2B—N7B | 1.6352 (17) | C12B—C13B | 1.373 (4) |
S2B—C9B | 1.763 (2) | C12B—H12B | 0.9300 |
N5A—C20A | 1.361 (3) | C13A—C14A | 1.379 (3) |
N5A—C18A | 1.368 (2) | C13A—H13A | 0.9300 |
N5A—C21A | 1.470 (2) | C13B—C14B | 1.377 (3) |
N5B—C20B | 1.354 (3) | C13B—H13B | 0.9300 |
N5B—C18B | 1.374 (2) | C14A—H14A | 0.9300 |
N5B—C21B | 1.456 (2) | C14B—H14B | 0.9300 |
N6A—C15A | 1.320 (2) | C15A—C19A | 1.390 (3) |
N6A—C16A | 1.341 (3) | C15B—C19B | 1.392 (3) |
N6B—C15B | 1.326 (3) | C16A—C17A | 1.361 (3) |
N6B—C16B | 1.340 (2) | C16B—C17B | 1.367 (3) |
N7A—C15A | 1.400 (2) | C17A—C18A | 1.392 (3) |
N7A—H7A | 0.8600 | C17A—H17A | 0.9300 |
N7B—C15B | 1.401 (2) | C17B—C18B | 1.389 (3) |
N7B—H7B | 0.8600 | C17B—H17B | 0.9300 |
N8A—C20A | 1.313 (2) | C18A—C19A | 1.396 (3) |
N8A—C19A | 1.392 (3) | C18B—C19B | 1.393 (3) |
N8B—C20B | 1.312 (2) | C20A—H20A | 0.9300 |
N8B—C19B | 1.385 (2) | C20B—H20B | 0.9300 |
C9A—C14A | 1.371 (3) | C21A—H21A | 0.9600 |
C9A—C10A | 1.380 (3) | C21A—H21B | 0.9600 |
C9B—C10B | 1.378 (3) | C21A—H21C | 0.9600 |
C9B—C14B | 1.380 (3) | C21B—H21D | 0.9600 |
C10A—C11A | 1.369 (4) | C21B—H21E | 0.9600 |
C10A—H10A | 0.9300 | C21B—H21F | 0.9600 |
O3A—S2A—O4A | 118.82 (10) | C12B—C13B—H13B | 120.0 |
O3A—S2A—N7A | 111.37 (10) | C14B—C13B—H13B | 120.0 |
O4A—S2A—N7A | 103.28 (9) | C9A—C14A—C13A | 119.1 (2) |
O3A—S2A—C9A | 108.41 (10) | C9A—C14A—H14A | 120.5 |
O4A—S2A—C9A | 107.92 (10) | C13A—C14A—H14A | 120.5 |
N7A—S2A—C9A | 106.31 (9) | C9B—C14B—C13B | 119.4 (2) |
O3B—S2B—O4B | 119.51 (9) | C9B—C14B—H14B | 120.3 |
O3B—S2B—N7B | 109.03 (9) | C13B—C14B—H14B | 120.3 |
O4B—S2B—N7B | 103.68 (9) | N6A—C15A—C19A | 121.52 (17) |
O3B—S2B—C9B | 108.80 (10) | N6A—C15A—N7A | 118.16 (17) |
O4B—S2B—C9B | 108.84 (9) | C19A—C15A—N7A | 120.32 (18) |
N7B—S2B—C9B | 106.16 (9) | N6B—C15B—C19B | 121.33 (17) |
C20A—N5A—C18A | 106.34 (15) | N6B—C15B—N7B | 117.25 (17) |
C20A—N5A—C21A | 126.50 (18) | C19B—C15B—N7B | 121.38 (18) |
C18A—N5A—C21A | 127.14 (18) | N6A—C16A—C17A | 127.47 (19) |
C20B—N5B—C18B | 106.11 (15) | N6A—C16A—Cl1A | 113.37 (16) |
C20B—N5B—C21B | 127.47 (19) | C17A—C16A—Cl1A | 119.14 (16) |
C18B—N5B—C21B | 126.40 (18) | N6B—C16B—C17B | 126.69 (19) |
C15A—N6A—C16A | 117.71 (17) | N6B—C16B—Cl1B | 115.09 (16) |
C15B—N6B—C16B | 118.25 (18) | C17B—C16B—Cl1B | 118.22 (15) |
C15A—N7A—S2A | 125.03 (15) | C16A—C17A—C18A | 113.45 (18) |
C15A—N7A—H7A | 117.5 | C16A—C17A—H17A | 123.3 |
S2A—N7A—H7A | 117.5 | C18A—C17A—H17A | 123.3 |
C15B—N7B—S2B | 123.79 (15) | C16B—C17B—C18B | 113.53 (18) |
C15B—N7B—H7B | 118.1 | C16B—C17B—H17B | 123.2 |
S2B—N7B—H7B | 118.1 | C18B—C17B—H17B | 123.2 |
C20A—N8A—C19A | 102.94 (16) | N5A—C18A—C17A | 133.00 (17) |
C20B—N8B—C19B | 103.25 (16) | N5A—C18A—C19A | 105.18 (17) |
C14A—C9A—C10A | 121.0 (2) | C17A—C18A—C19A | 121.82 (18) |
C14A—C9A—S2A | 120.72 (17) | N5B—C18B—C17B | 132.22 (17) |
C10A—C9A—S2A | 118.14 (18) | N5B—C18B—C19B | 105.20 (17) |
C10B—C9B—C14B | 120.8 (2) | C17B—C18B—C19B | 122.51 (18) |
C10B—C9B—S2B | 119.93 (17) | N8A—C19A—C15A | 131.09 (17) |
C14B—C9B—S2B | 119.24 (16) | N8A—C19A—C18A | 110.89 (17) |
C11A—C10A—C9A | 118.7 (3) | C15A—C19A—C18A | 118.02 (18) |
C11A—C10A—H10A | 120.7 | N8B—C19B—C18B | 110.79 (17) |
C9A—C10A—H10A | 120.7 | N8B—C19B—C15B | 131.45 (17) |
C9B—C10B—C11B | 118.7 (2) | C18B—C19B—C15B | 117.66 (18) |
C9B—C10B—H10B | 120.6 | N8A—C20A—N5A | 114.65 (19) |
C11B—C10B—H10B | 120.6 | N8A—C20A—H20A | 122.7 |
C10A—C11A—C12A | 120.6 (3) | N5A—C20A—H20A | 122.7 |
C10A—C11A—H11A | 119.7 | N8B—C20B—N5B | 114.65 (18) |
C12A—C11A—H11A | 119.7 | N8B—C20B—H20B | 122.7 |
C12B—C11B—C10B | 120.6 (2) | N5B—C20B—H20B | 122.7 |
C12B—C11B—H11B | 119.7 | N5A—C21A—H21A | 109.5 |
C10B—C11B—H11B | 119.7 | N5A—C21A—H21B | 109.5 |
C13A—C12A—C11A | 120.2 (2) | H21A—C21A—H21B | 109.5 |
C13A—C12A—H12A | 119.9 | N5A—C21A—H21C | 109.5 |
C11A—C12A—H12A | 119.9 | H21A—C21A—H21C | 109.5 |
C11B—C12B—C13B | 120.3 (2) | H21B—C21A—H21C | 109.5 |
C11B—C12B—H12B | 119.8 | N5B—C21B—H21D | 109.5 |
C13B—C12B—H12B | 119.8 | N5B—C21B—H21E | 109.5 |
C12A—C13A—C14A | 120.4 (3) | H21D—C21B—H21E | 109.5 |
C12A—C13A—H13A | 119.8 | N5B—C21B—H21F | 109.5 |
C14A—C13A—H13A | 119.8 | H21D—C21B—H21F | 109.5 |
C12B—C13B—C14B | 120.0 (2) | H21E—C21B—H21F | 109.5 |
O3A—S2A—N7A—C15A | 54.0 (2) | C15B—N6B—C16B—C17B | −0.4 (3) |
O4A—S2A—N7A—C15A | −177.38 (17) | C15B—N6B—C16B—Cl1B | 179.63 (15) |
C9A—S2A—N7A—C15A | −63.9 (2) | N6A—C16A—C17A—C18A | 0.2 (3) |
O3B—S2B—N7B—C15B | 42.58 (18) | Cl1A—C16A—C17A—C18A | −177.92 (14) |
O4B—S2B—N7B—C15B | 170.92 (16) | N6B—C16B—C17B—C18B | −1.1 (3) |
C9B—S2B—N7B—C15B | −74.47 (18) | Cl1B—C16B—C17B—C18B | 178.91 (15) |
O3A—S2A—C9A—C14A | −20.6 (2) | C20A—N5A—C18A—C17A | 179.0 (2) |
O4A—S2A—C9A—C14A | −150.49 (17) | C21A—N5A—C18A—C17A | −2.4 (3) |
N7A—S2A—C9A—C14A | 99.25 (18) | C20A—N5A—C18A—C19A | −0.8 (2) |
O3A—S2A—C9A—C10A | 155.31 (17) | C21A—N5A—C18A—C19A | 177.74 (17) |
O4A—S2A—C9A—C10A | 25.4 (2) | C16A—C17A—C18A—N5A | −179.73 (19) |
N7A—S2A—C9A—C10A | −84.85 (19) | C16A—C17A—C18A—C19A | 0.1 (3) |
O3B—S2B—C9B—C10B | −14.6 (2) | C20B—N5B—C18B—C17B | −176.7 (2) |
O4B—S2B—C9B—C10B | −146.40 (17) | C21B—N5B—C18B—C17B | 2.1 (3) |
N7B—S2B—C9B—C10B | 102.56 (18) | C20B—N5B—C18B—C19B | 0.0 (2) |
O3B—S2B—C9B—C14B | 166.09 (16) | C21B—N5B—C18B—C19B | 178.77 (19) |
O4B—S2B—C9B—C14B | 34.3 (2) | C16B—C17B—C18B—N5B | 177.4 (2) |
N7B—S2B—C9B—C14B | −76.70 (18) | C16B—C17B—C18B—C19B | 1.2 (3) |
C14A—C9A—C10A—C11A | 1.7 (4) | C20A—N8A—C19A—C15A | −179.5 (2) |
S2A—C9A—C10A—C11A | −174.2 (2) | C20A—N8A—C19A—C18A | 0.2 (2) |
C14B—C9B—C10B—C11B | −0.4 (3) | N6A—C15A—C19A—N8A | 178.71 (19) |
S2B—C9B—C10B—C11B | −179.61 (18) | N7A—C15A—C19A—N8A | −0.5 (3) |
C9A—C10A—C11A—C12A | −0.3 (4) | N6A—C15A—C19A—C18A | −1.0 (3) |
C9B—C10B—C11B—C12B | 0.7 (4) | N7A—C15A—C19A—C18A | 179.78 (17) |
C10A—C11A—C12A—C13A | −0.9 (5) | N5A—C18A—C19A—N8A | 0.4 (2) |
C10B—C11B—C12B—C13B | −0.5 (4) | C17A—C18A—C19A—N8A | −179.47 (17) |
C11A—C12A—C13A—C14A | 0.8 (4) | N5A—C18A—C19A—C15A | −179.87 (16) |
C11B—C12B—C13B—C14B | −0.2 (4) | C17A—C18A—C19A—C15A | 0.3 (3) |
C10A—C9A—C14A—C13A | −1.7 (3) | C20B—N8B—C19B—C18B | 0.4 (2) |
S2A—C9A—C14A—C13A | 174.03 (18) | C20B—N8B—C19B—C15B | 176.6 (2) |
C12A—C13A—C14A—C9A | 0.5 (4) | N5B—C18B—C19B—N8B | −0.3 (2) |
C10B—C9B—C14B—C13B | −0.3 (3) | C17B—C18B—C19B—N8B | 176.86 (18) |
S2B—C9B—C14B—C13B | 178.94 (18) | N5B—C18B—C19B—C15B | −177.09 (17) |
C12B—C13B—C14B—C9B | 0.6 (4) | C17B—C18B—C19B—C15B | 0.0 (3) |
C16A—N6A—C15A—C19A | 1.2 (3) | N6B—C15B—C19B—N8B | −177.66 (19) |
C16A—N6A—C15A—N7A | −179.50 (18) | N7B—C15B—C19B—N8B | 0.0 (3) |
S2A—N7A—C15A—N6A | −9.7 (3) | N6B—C15B—C19B—C18B | −1.6 (3) |
S2A—N7A—C15A—C19A | 169.53 (15) | N7B—C15B—C19B—C18B | 176.01 (17) |
C16B—N6B—C15B—C19B | 1.8 (3) | C19A—N8A—C20A—N5A | −0.8 (2) |
C16B—N6B—C15B—N7B | −175.93 (17) | C18A—N5A—C20A—N8A | 1.1 (2) |
S2B—N7B—C15B—N6B | 21.4 (2) | C21A—N5A—C20A—N8A | −177.51 (18) |
S2B—N7B—C15B—C19B | −156.28 (15) | C19B—N8B—C20B—N5B | −0.4 (2) |
C15A—N6A—C16A—C17A | −0.9 (3) | C18B—N5B—C20B—N8B | 0.2 (2) |
C15A—N6A—C16A—Cl1A | 177.34 (15) | C21B—N5B—C20B—N8B | −178.51 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7A—H7A···N8Bi | 0.86 | 2.25 | 3.014 (2) | 148 |
N7B—H7B···N8Aii | 0.86 | 2.25 | 3.092 (2) | 165 |
C13A—H13A···Cl1Aiii | 0.93 | 2.82 | 3.620 (3) | 144 |
C20A—H20A···O4Aiv | 0.93 | 2.47 | 3.243 (3) | 141 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N7A—H7A···N8Bi | 0.86 | 2.25 | 3.014 (2) | 148 |
N7B—H7B···N8Aii | 0.86 | 2.25 | 3.092 (2) | 165 |
C13A—H13A···Cl1Aiii | 0.93 | 2.82 | 3.620 (3) | 144 |
C20A—H20A···O4Aiv | 0.93 | 2.47 | 3.243 (3) | 141 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2. |
Acknowledgements
We thank the DST, India for funding under DST–FIST (Level II) for the X-ray diffraction facility at SSCU, IISc, Bangalore.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Imidazo[4,5]pyridine derivatives have been reported as inhibitors of mitogen and stress-activated protein kinases and aurora kinases (Kulkarni & Newman, 2007). As part of our studies of this family of compounds, we now describe the synthesis and structure of the title compound. Its gometrical data are good agreement with those of a related structure (Kandri Rodi et al., 2013)
The asymmetric unit contains two independent molecules A and B respectively are shown in Fig. 1. The 1H-imidazo [4,5-c]pyridine rings system are nearly planar, with a maximum deviations of 0.0284 (19) Å and 0.0061 (19) Å for the atoms C19a and C19b; the dihedral angles between the 1H-imidazo [4,5-c]pyridine (N5a/N6a/N8a/C15a–C20a) & (N5b/N6b/N8b/C15b–C20a) and the terminal benzene (C9a–C14a) & (C9b–C14b) rings are 80.83 (10)° and 62.34 (1)°.
In the crystal, A-B dimers are linked by pairs of N—H···N hydrogen bonds (Table 1), which generate R22(10) loops. The dimers are lined by C—H···O and C—H···Cl interactions to generate a three-dimensional network. Aromatic π–π stacking interactions [shortest centroid–centroid distance = 3.5211 (12) Å] are also observed.