organic compounds
4-(4-Chlorophenyl)-N-[(E)-4-(dimethylamino)benzylidene]-1,3-thiazol-2-amine
aDepartment of Physics, Government First Grade College, Bidadi, Bangalore 560 067, India, bOrganic Chemistry Division, Vivekananda Degree Collage, Bangalore 560 055, India, cDepartment of Physics, Government First Grade College, Mandya 571 401, India, dMaterials Research Center, Indian Institute of Science, Bangalore 560 012, India, and eBioinformatics Infrastructure Facility, School of Life Sciences, University of Hyderabad, Hyderabad 500 046, India
*Correspondence e-mail: rsrsl@uohyd.ernet.in
The title compound, C18H16ClN3S, adopts an extended molecular structure. The thiazole ring is inclined by 9.2 (1) and 15.3 (1)° with respect to the chlorophenyl and 4-(dimethylamino)phenyl rings, respectively, while the benzene ring planes make an angle of 19.0 (1)°. A weak intermolecular C—H⋯π contact is observed in the crystal structure.
Related literature
For related structures, see: Lynch et al. (1999; 2002). For medicinal applications of thiazole derivatives, see: Misra et al. (2004).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2010); cell SAINT-Plus (Bruker, 2010); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536811028078/xu5251sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811028078/xu5251Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811028078/xu5251Isup3.cml
A mixture of 2-amino-4-(4-chloro) phenyl thiazole (0.01 mol; CAS No. 2103–99-3) and paradimethyl amino benzaldehyde (0.01 mol) in ethanol (30 ml), and catalytic amount of glacial acetic acid (2 ml) in a clean conical flask was refluxed for 2 h. The resulting mixture was cooled, filtered and dried to get the title compound (m.p. 506–507°C). To obtain the suitable single crystals for X-ray diffraction, (I) was mixed with DMF (30 ml) and heated until completely dissolved. The mixture was left for slow evaporation.
Hydrogen atoms were placed in their stereochemically expected positions and refined with the riding options. Methyl hydrogen atoms were fixed with reference to local
The distances with hydrogen atoms are as follows: C(aromatic/sp2)—H = 0.93 Å, C(methyl)—H = 0.96 Å, and Uiso = 1.2 Ueq(parent) [1.5Ueq(parent) for methyl groups].Data collection: APEX2 (Bruker, 2010); cell
SAINT-Plus (Bruker, 2010); data reduction: SAINT-Plus (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).Fig. 1. A view of (I) with adopted atom-numbering scheme and non-H atoms shown as probability ellipsoids at 30% levels. |
C18H16ClN3S | F(000) = 356 |
Mr = 341.85 | Dx = 1.374 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1055 reflections |
a = 6.1169 (7) Å | θ = 2.2–29.2° |
b = 7.4708 (8) Å | µ = 0.36 mm−1 |
c = 18.2536 (18) Å | T = 294 K |
β = 97.975 (11)° | Needle, brown |
V = 826.09 (15) Å3 | 0.24 × 0.18 × 0.16 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 3242 independent reflections |
Radiation source: fine-focus sealed tube | 1355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
ϕ and ω scans | θmax = 26.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −7→7 |
Tmin = 0.919, Tmax = 0.945 | k = −9→9 |
9063 measured reflections | l = −22→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.78 | (Δ/σ)max = 0.004 |
3242 reflections | Δρmax = 0.18 e Å−3 |
210 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1483 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (8) |
C18H16ClN3S | V = 826.09 (15) Å3 |
Mr = 341.85 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.1169 (7) Å | µ = 0.36 mm−1 |
b = 7.4708 (8) Å | T = 294 K |
c = 18.2536 (18) Å | 0.24 × 0.18 × 0.16 mm |
β = 97.975 (11)° |
Bruker APEXII CCD diffractometer | 3242 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1355 reflections with I > 2σ(I) |
Tmin = 0.919, Tmax = 0.945 | Rint = 0.084 |
9063 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.062 | Δρmax = 0.18 e Å−3 |
S = 0.78 | Δρmin = −0.20 e Å−3 |
3242 reflections | Absolute structure: Flack (1983), 1483 Friedel pairs |
210 parameters | Absolute structure parameter: 0.06 (8) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = -0.44990(0.00160) m2 = -0.87347(0.00086) m3 = -0.18611(0.00175) D = -3.47756(0.01551) Atom d s d/s (d/s)**2 C1 * -0.0082 0.0048 - 1.706 2.911 C2 * 0.0089 0.0046 1.925 3.707 C3 * -0.0021 0.0045 - 0.472 0.223 C4 * -0.0040 0.0039 - 1.036 1.072 C5 * 0.0051 0.0039 1.304 1.700 C6 * -0.0004 0.0040 - 0.096 0.009 Cl1 - 0.0062 0.0013 - 4.835 23.378 C7 - 0.0409 0.0039 - 10.501 110.265 ============ Sum((d/s)**2) for starred atoms 9.623 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 2 m1 = -0.34887(0.00131) m2 = -0.93392(0.00058) m3 = -0.07797(0.00194) D = -2.96690(0.02047) Atom d s d/s (d/s)**2 N1 * 0.0036 0.0034 1.053 1.108 S1 * 0.0002 0.0012 0.201 0.041 C7 * -0.0021 0.0039 - 0.541 0.293 C8 * -0.0007 0.0043 - 0.157 0.025 C9 * -0.0054 0.0042 - 1.283 1.647 N2 - 0.0838 0.0039 - 21.454 460.260 C4 - 0.0329 0.0039 - 8.470 71.739 ============ Sum((d/s)**2) for starred atoms 3.113 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms does not deviate significantly from planarity Plane 3 m1 = 0.47925(0.00159) m2 = 0.86590(0.00089) m3 = -0.14330(0.00169) D = -0.77606(0.02916) Atom d s d/s (d/s)**2 C11 * 0.0080 0.0041 1.980 3.920 C12 * -0.0093 0.0041 - 2.291 5.251 C13 * 0.0037 0.0043 0.856 0.733 C14 * 0.0043 0.0042 1.010 1.021 C15 * -0.0044 0.0038 - 1.160 1.346 C16 * -0.0009 0.0040 - 0.219 0.048 N3 0.0139 0.0033 4.236 17.942 C10 0.0759 0.0041 18.730 350.815 ============ Sum((d/s)**2) for starred atoms 12.318 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 4 m1 = 0.46397(0.00261) m2 = 0.88241(0.00119) m3 = -0.07795(0.00540) D = 0.57261(0.10767) Atom d s d/s (d/s)**2 N3 * 0.0000 0.0033 0.000 0.000 C17 * 0.0000 0.0040 0.000 0.000 C18 * 0.0000 0.0041 0.000 0.000 C14 - 0.0851 0.0042 - 20.162 406.523 ============ Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 9.17 (0.13) 170.83 (0.13) 1 3 19.04 (0.14) 160.96 (0.14) 1 4 15.20 (0.31) 164.80 (0.31) 2 3 15.27 (0.13) 164.73 (0.13) 2 4 11.51 (0.27) 168.49 (0.27) 3 4 3.96 (0.31) 176.04 (0.31) |
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 > σ(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 | ||
S1 | −0.58295 (18) | 0.55168 (16) | 0.68740 (6) | 0.0603 (4) | |
Cl1 | −0.0164 (2) | 0.44097 (17) | 0.29270 (6) | 0.0840 (5) | |
N1 | −0.2184 (5) | 0.4428 (5) | 0.64682 (18) | 0.0417 (9) | |
N2 | −0.2363 (6) | 0.4507 (5) | 0.77983 (19) | 0.0541 (10) | |
N3 | 0.3895 (6) | 0.3460 (4) | 1.0889 (2) | 0.0448 (10) | |
C1 | −0.1183 (8) | 0.4555 (6) | 0.3769 (2) | 0.0504 (13) | |
C2 | −0.3184 (7) | 0.5363 (6) | 0.3800 (2) | 0.0577 (13) | |
H2 | −0.4002 | 0.5824 | 0.3374 | 0.069* | |
C3 | −0.3970 (6) | 0.5480 (6) | 0.4478 (2) | 0.0490 (12) | |
H3 | −0.5311 | 0.6045 | 0.4506 | 0.059* | |
C4 | −0.2781 (6) | 0.4765 (5) | 0.5114 (2) | 0.0340 (11) | |
C5 | −0.0787 (6) | 0.3928 (5) | 0.5059 (2) | 0.0445 (13) | |
H5 | 0.0023 | 0.3429 | 0.5478 | 0.053* | |
C6 | 0.0014 (7) | 0.3830 (5) | 0.4382 (2) | 0.0473 (13) | |
H6 | 0.1356 | 0.3273 | 0.4349 | 0.057* | |
C7 | −0.3576 (7) | 0.4909 (5) | 0.5840 (2) | 0.0373 (12) | |
C8 | −0.5606 (6) | 0.5520 (6) | 0.5945 (2) | 0.0512 (12) | |
H8 | −0.6706 | 0.5884 | 0.5571 | 0.061* | |
C9 | −0.3158 (6) | 0.4695 (6) | 0.7050 (3) | 0.0491 (13) | |
C10 | −0.0454 (7) | 0.3803 (5) | 0.7958 (2) | 0.0442 (13) | |
H10 | 0.0264 | 0.3374 | 0.7577 | 0.053* | |
C11 | 0.0633 (7) | 0.3650 (5) | 0.8714 (3) | 0.0369 (11) | |
C12 | −0.0298 (6) | 0.4390 (6) | 0.9301 (2) | 0.0422 (11) | |
H12 | −0.1679 | 0.4928 | 0.9206 | 0.051* | |
C13 | 0.0767 (6) | 0.4348 (6) | 1.0015 (2) | 0.0422 (12) | |
H13 | 0.0112 | 0.4879 | 1.0391 | 0.051* | |
C14 | 0.2839 (7) | 0.3510 (6) | 1.0185 (2) | 0.0376 (12) | |
C15 | 0.3763 (7) | 0.2732 (5) | 0.9598 (2) | 0.0415 (12) | |
H15 | 0.5122 | 0.2158 | 0.9690 | 0.050* | |
C16 | 0.2669 (7) | 0.2815 (5) | 0.8887 (2) | 0.0466 (13) | |
H16 | 0.3318 | 0.2293 | 0.8508 | 0.056* | |
C17 | 0.2862 (6) | 0.4146 (6) | 1.1505 (2) | 0.0654 (15) | |
H17C | 0.1580 | 0.3443 | 1.1559 | 0.098* | |
H17B | 0.2435 | 0.5370 | 1.1411 | 0.098* | |
H17A | 0.3891 | 0.4078 | 1.1952 | 0.098* | |
C18 | 0.6027 (7) | 0.2620 (6) | 1.1087 (2) | 0.0608 (14) | |
H18A | 0.7059 | 0.3112 | 1.0790 | 0.091* | |
H18B | 0.5894 | 0.1354 | 1.1002 | 0.091* | |
H18C | 0.6543 | 0.2836 | 1.1600 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0511 (8) | 0.0798 (10) | 0.0498 (9) | 0.0126 (8) | 0.0057 (7) | −0.0004 (8) |
Cl1 | 0.1220 (12) | 0.0840 (10) | 0.0528 (9) | −0.0034 (9) | 0.0367 (9) | 0.0026 (8) |
N1 | 0.045 (2) | 0.048 (2) | 0.032 (2) | 0.010 (2) | 0.0036 (19) | −0.003 (2) |
N2 | 0.047 (2) | 0.072 (3) | 0.044 (3) | 0.005 (2) | 0.009 (2) | 0.002 (2) |
N3 | 0.050 (3) | 0.047 (3) | 0.041 (3) | 0.014 (2) | 0.018 (2) | 0.001 (2) |
C1 | 0.072 (4) | 0.039 (3) | 0.043 (3) | −0.006 (3) | 0.016 (3) | 0.003 (3) |
C2 | 0.074 (4) | 0.056 (3) | 0.043 (3) | 0.009 (3) | 0.006 (3) | 0.019 (3) |
C3 | 0.052 (3) | 0.048 (3) | 0.045 (3) | −0.003 (3) | −0.001 (3) | 0.007 (3) |
C4 | 0.040 (3) | 0.028 (3) | 0.035 (3) | −0.005 (2) | 0.006 (2) | −0.002 (2) |
C5 | 0.050 (3) | 0.044 (3) | 0.039 (3) | 0.005 (2) | 0.005 (3) | 0.002 (2) |
C6 | 0.053 (3) | 0.041 (3) | 0.049 (3) | 0.001 (3) | 0.015 (3) | −0.007 (3) |
C7 | 0.043 (3) | 0.026 (3) | 0.042 (3) | −0.002 (2) | 0.000 (2) | −0.004 (2) |
C8 | 0.051 (3) | 0.059 (3) | 0.042 (3) | 0.003 (3) | −0.002 (2) | −0.001 (3) |
C9 | 0.048 (3) | 0.045 (3) | 0.052 (3) | 0.009 (2) | −0.001 (3) | 0.001 (3) |
C10 | 0.057 (3) | 0.040 (3) | 0.039 (3) | −0.008 (3) | 0.015 (3) | −0.006 (2) |
C11 | 0.039 (3) | 0.038 (3) | 0.035 (3) | −0.003 (2) | 0.008 (3) | −0.001 (2) |
C12 | 0.037 (3) | 0.046 (3) | 0.046 (3) | 0.003 (2) | 0.013 (3) | −0.006 (3) |
C13 | 0.041 (3) | 0.053 (3) | 0.034 (3) | 0.006 (3) | 0.011 (2) | 0.001 (3) |
C14 | 0.046 (3) | 0.037 (3) | 0.033 (3) | −0.001 (2) | 0.016 (3) | 0.006 (2) |
C15 | 0.042 (3) | 0.045 (3) | 0.038 (3) | 0.012 (2) | 0.006 (3) | −0.008 (3) |
C16 | 0.049 (3) | 0.046 (3) | 0.047 (3) | 0.004 (2) | 0.015 (3) | −0.004 (3) |
C17 | 0.066 (3) | 0.089 (4) | 0.042 (3) | 0.018 (3) | 0.013 (3) | −0.003 (3) |
C18 | 0.055 (4) | 0.074 (4) | 0.050 (4) | 0.015 (3) | −0.005 (3) | 0.001 (3) |
S1—C8 | 1.720 (4) | C7—C8 | 1.362 (4) |
S1—C9 | 1.733 (4) | C8—H8 | 0.9300 |
Cl1—C1 | 1.741 (4) | C10—C11 | 1.451 (5) |
N1—C9 | 1.303 (4) | C10—H10 | 0.9300 |
N1—C7 | 1.378 (4) | C11—C16 | 1.390 (5) |
N2—C10 | 1.277 (4) | C11—C12 | 1.394 (4) |
N2—C9 | 1.393 (4) | C12—C13 | 1.375 (4) |
N3—C14 | 1.357 (5) | C12—H12 | 0.9300 |
N3—C18 | 1.447 (5) | C13—C14 | 1.409 (5) |
N3—C17 | 1.458 (4) | C13—H13 | 0.9300 |
C1—C6 | 1.361 (5) | C14—C15 | 1.404 (5) |
C1—C2 | 1.373 (5) | C15—C16 | 1.377 (5) |
C2—C3 | 1.392 (4) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.388 (5) | C17—H17C | 0.9600 |
C3—H3 | 0.9300 | C17—H17B | 0.9600 |
C4—C5 | 1.386 (5) | C17—H17A | 0.9600 |
C4—C7 | 1.477 (4) | C18—H18A | 0.9600 |
C5—C6 | 1.394 (4) | C18—H18B | 0.9600 |
C5—H5 | 0.9300 | C18—H18C | 0.9600 |
C6—H6 | 0.9300 | ||
C8—S1—C9 | 88.9 (2) | N2—C10—C11 | 122.3 (4) |
C9—N1—C7 | 109.8 (3) | N2—C10—H10 | 118.9 |
C10—N2—C9 | 116.7 (4) | C11—C10—H10 | 118.9 |
C14—N3—C18 | 122.9 (3) | C16—C11—C12 | 116.9 (4) |
C14—N3—C17 | 121.4 (3) | C16—C11—C10 | 121.9 (4) |
C18—N3—C17 | 115.6 (4) | C12—C11—C10 | 121.1 (4) |
C6—C1—C2 | 121.5 (4) | C13—C12—C11 | 121.9 (4) |
C6—C1—Cl1 | 118.9 (4) | C13—C12—H12 | 119.0 |
C2—C1—Cl1 | 119.6 (4) | C11—C12—H12 | 119.0 |
C1—C2—C3 | 118.9 (4) | C12—C13—C14 | 120.8 (4) |
C1—C2—H2 | 120.6 | C12—C13—H13 | 119.6 |
C3—C2—H2 | 120.6 | C14—C13—H13 | 119.6 |
C4—C3—C2 | 120.9 (4) | N3—C14—C15 | 121.5 (4) |
C4—C3—H3 | 119.5 | N3—C14—C13 | 121.0 (4) |
C2—C3—H3 | 119.5 | C15—C14—C13 | 117.5 (4) |
C5—C4—C3 | 118.6 (3) | C16—C15—C14 | 120.4 (4) |
C5—C4—C7 | 120.0 (4) | C16—C15—H15 | 119.8 |
C3—C4—C7 | 121.5 (4) | C14—C15—H15 | 119.8 |
C4—C5—C6 | 120.6 (4) | C15—C16—C11 | 122.5 (4) |
C4—C5—H5 | 119.7 | C15—C16—H16 | 118.8 |
C6—C5—H5 | 119.7 | C11—C16—H16 | 118.8 |
C1—C6—C5 | 119.5 (4) | N3—C17—H17C | 109.5 |
C1—C6—H6 | 120.3 | N3—C17—H17B | 109.5 |
C5—C6—H6 | 120.3 | H17C—C17—H17B | 109.5 |
C8—C7—N1 | 116.1 (4) | N3—C17—H17A | 109.5 |
C8—C7—C4 | 124.8 (4) | H17C—C17—H17A | 109.5 |
N1—C7—C4 | 119.1 (4) | H17B—C17—H17A | 109.5 |
C7—C8—S1 | 109.7 (3) | N3—C18—H18A | 109.5 |
C7—C8—H8 | 125.1 | N3—C18—H18B | 109.5 |
S1—C8—H8 | 125.1 | H18A—C18—H18B | 109.5 |
N1—C9—N2 | 130.3 (4) | N3—C18—H18C | 109.5 |
N1—C9—S1 | 115.5 (3) | H18A—C18—H18C | 109.5 |
N2—C9—S1 | 114.1 (3) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | 1.7 (7) | C10—N2—C9—N1 | −7.6 (7) |
Cl1—C1—C2—C3 | −179.6 (3) | C10—N2—C9—S1 | 175.8 (3) |
C1—C2—C3—C4 | −1.2 (7) | C8—S1—C9—N1 | −0.6 (4) |
C2—C3—C4—C5 | 0.0 (6) | C8—S1—C9—N2 | 176.5 (3) |
C2—C3—C4—C7 | 178.9 (4) | C9—N2—C10—C11 | 175.4 (4) |
C3—C4—C5—C6 | 0.8 (6) | N2—C10—C11—C16 | 177.2 (4) |
C7—C4—C5—C6 | −178.1 (4) | N2—C10—C11—C12 | −4.8 (6) |
C2—C1—C6—C5 | −1.0 (7) | C16—C11—C12—C13 | 1.9 (6) |
Cl1—C1—C6—C5 | −179.7 (3) | C10—C11—C12—C13 | −176.2 (4) |
C4—C5—C6—C1 | −0.3 (6) | C11—C12—C13—C14 | −1.5 (7) |
C9—N1—C7—C8 | −0.7 (5) | C18—N3—C14—C15 | 0.2 (6) |
C9—N1—C7—C4 | 178.3 (4) | C17—N3—C14—C15 | −175.3 (4) |
C5—C4—C7—C8 | −172.4 (4) | C18—N3—C14—C13 | −179.8 (4) |
C3—C4—C7—C8 | 8.8 (6) | C17—N3—C14—C13 | 4.8 (6) |
C5—C4—C7—N1 | 8.8 (5) | C12—C13—C14—N3 | −179.8 (4) |
C3—C4—C7—N1 | −170.0 (4) | C12—C13—C14—C15 | 0.2 (6) |
N1—C7—C8—S1 | 0.3 (5) | N3—C14—C15—C16 | −179.4 (4) |
C4—C7—C8—S1 | −178.6 (3) | C13—C14—C15—C16 | 0.6 (6) |
C9—S1—C8—C7 | 0.1 (3) | C14—C15—C16—C11 | −0.2 (6) |
C7—N1—C9—N2 | −175.7 (4) | C12—C11—C16—C15 | −1.0 (6) |
C7—N1—C9—S1 | 0.8 (5) | C10—C11—C16—C15 | 177.0 (4) |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···Cgi | 0.96 | 2.73 | 3.515 (5) | 140 |
Symmetry code: (i) −x+1, y−1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H16ClN3S |
Mr | 341.85 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 6.1169 (7), 7.4708 (8), 18.2536 (18) |
β (°) | 97.975 (11) |
V (Å3) | 826.09 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.24 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.919, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9063, 3242, 1355 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.062, 0.78 |
No. of reflections | 3242 |
No. of parameters | 210 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Absolute structure | Flack (1983), 1483 Friedel pairs |
Absolute structure parameter | 0.06 (8) |
Computer programs: APEX2 (Bruker, 2010), SAINT-Plus (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2009).
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···Cgi | 0.96 | 2.73 | 3.515 (5) | 140 |
Symmetry code: (i) −x+1, y−1/2, −z+2. |
Acknowledgements
We acknowledge the CCD facility, set up under the IRHPA–DST program at the IISc., Bangalore. RSR acknowledges the CSIR, Government of India, for funding under the scientist's pool scheme.
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.
The title compound, C18H16ClN3S, (I), is a 2-amino-thiazole derivative. Few structures of such derivatives have been determined (Lynch et al., 1999; 2002) and some of them have been shown to act as inhibitor of cyclin-dependent kinase (Misra et al., 2004). The structure of (I) with adopted atom-numbering scheme is shown in Fig 1.
(I) adopts an extended structure. The thiazole ring is inclined with respect to chlorophenyl and dimethylaminophenyl rings by 9.2 (1)° and 15.3 (1)°, respectively, while both benzene ring planes make an angle of 19.0 (1)°. The dimethylamino group makes an angle of 4.0 (3)° with respect to the adjacent benzene ring. The crystal packing is governed by van der waals interactions only. Short intermolecular C—H···π contact is also observed (Table 1).