Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011771/bt6063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011771/bt6063Isup2.hkl |
CCDC reference: 170908
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.071
- wR factor = 0.217
- Data-to-parameter ratio = 17.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
PLAT_030 Alert B Refined Extinction parameter within range .... 2.00 Sigma
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
The title compound was synthesized by the condensation of 4,6-dimethylquinoline-2-carbaldehyde with o-chloroaniline in dry benzene over a period of 11 h. Light-yellow crystals were obtained after crystallization from petroleum ether (313–333 K). Yield: 81%; m.p.: 405 K; IR (KBr): γ = 3030, 2900, 1580 cm-1; 1H NMR (CDCl3, δ, 200 MHz): 2.58 (3H, s, 6-CH3), 2.74 (3H, s, 4-CH3), 7.12–8.65 (9H, m, ArH and CH) p.p.m.; UV (CHCl3): λmax = 262.3, 314.4 nm. Elemental analysis, C18H15N2 requires: C 73.34, H 5.13, N 9.50%; found: C 73.18, H 5.07, N 9.43% (Aydo~gan, 1993).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).
C18H15ClN2 | Z = 2 |
Mr = 294.77 | F(000) = 308 |
Triclinic, P1 | Dx = 1.278 Mg m−3 |
a = 7.4962 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5511 (9) Å | Cell parameters from 1530 reflections |
c = 11.4013 (11) Å | θ = 2.8–27.5° |
α = 79.039 (2)° | µ = 0.24 mm−1 |
β = 76.866 (2)° | T = 293 K |
γ = 76.886 (2)° | Needle, light yellow |
V = 765.90 (13) Å3 | 0.34 × 0.22 × 0.10 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 3363 independent reflections |
Radiation source: fine-focus sealed tube | 1573 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
ω scans | h = −8→9 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.922, Tmax = 0.976 | l = −12→14 |
4930 measured reflections |
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)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.217 | w = 1/[σ2(Fo2) + (0.0995P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.006 |
3363 reflections | Δρmax = 0.24 e Å−3 |
193 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (6) |
C18H15ClN2 | γ = 76.886 (2)° |
Mr = 294.77 | V = 765.90 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4962 (7) Å | Mo Kα radiation |
b = 9.5511 (9) Å | µ = 0.24 mm−1 |
c = 11.4013 (11) Å | T = 293 K |
α = 79.039 (2)° | 0.34 × 0.22 × 0.10 mm |
β = 76.866 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3363 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1573 reflections with I > 2σ(I) |
Tmin = 0.922, Tmax = 0.976 | Rint = 0.040 |
4930 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.24 e Å−3 |
3363 reflections | Δρmin = −0.29 e Å−3 |
193 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. |
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. |
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 | ||
Cl1 | 0.09265 (15) | 0.64820 (14) | 0.13413 (10) | 0.0847 (5) | |
N1 | −0.2795 (4) | 0.1499 (3) | 0.2679 (3) | 0.0529 (8) | |
N2 | −0.2447 (4) | 0.5196 (3) | 0.2078 (3) | 0.0557 (8) | |
C1 | −0.2753 (5) | 0.2763 (4) | 0.2971 (3) | 0.0504 (9) | |
C2 | −0.2659 (5) | 0.2931 (4) | 0.4162 (3) | 0.0535 (9) | |
H2B | −0.2652 | 0.3846 | 0.4327 | 0.064* | |
C3 | −0.2581 (5) | 0.1783 (4) | 0.5066 (3) | 0.0496 (9) | |
C4 | −0.2561 (4) | 0.0402 (4) | 0.4773 (3) | 0.0467 (8) | |
C5 | −0.2413 (5) | −0.0895 (4) | 0.5605 (3) | 0.0558 (9) | |
H5A | −0.2324 | −0.0855 | 0.6398 | 0.067* | |
C6 | −0.2397 (5) | −0.2211 (4) | 0.5288 (4) | 0.0608 (10) | |
C7 | −0.2565 (5) | −0.2259 (4) | 0.4094 (4) | 0.0635 (11) | |
H7A | −0.2580 | −0.3145 | 0.3874 | 0.076* | |
C8 | −0.2707 (5) | −0.1043 (4) | 0.3256 (4) | 0.0614 (10) | |
H8A | −0.2811 | −0.1108 | 0.2471 | 0.074* | |
C9 | −0.2699 (4) | 0.0319 (4) | 0.3562 (3) | 0.0496 (9) | |
C10 | −0.2508 (6) | 0.1982 (4) | 0.6332 (3) | 0.0664 (11) | |
H10A | −0.2508 | 0.2984 | 0.6347 | 0.100* | |
H10B | −0.1391 | 0.1388 | 0.6565 | 0.100* | |
H10C | −0.3578 | 0.1702 | 0.6891 | 0.100* | |
C11 | −0.2192 (7) | −0.3590 (4) | 0.6193 (4) | 0.0807 (13) | |
H11A | −0.2231 | −0.3352 | 0.6980 | 0.121* | |
H11B | −0.1021 | −0.4211 | 0.5935 | 0.121* | |
H11C | −0.3195 | −0.4081 | 0.6236 | 0.121* | |
C12 | −0.2763 (5) | 0.3988 (4) | 0.1977 (3) | 0.0545 (9) | |
H12A | −0.3013 | 0.3869 | 0.1243 | 0.065* | |
C13 | −0.2514 (5) | 0.6330 (4) | 0.1083 (3) | 0.0509 (9) | |
C14 | −0.4048 (6) | 0.6813 (5) | 0.0530 (4) | 0.0702 (11) | |
H14A | −0.5047 | 0.6329 | 0.0773 | 0.084* | |
C15 | −0.4128 (8) | 0.7990 (5) | −0.0371 (4) | 0.0865 (14) | |
H15A | −0.5184 | 0.8311 | −0.0720 | 0.104* | |
C16 | −0.2639 (8) | 0.8698 (5) | −0.0757 (4) | 0.0865 (14) | |
H16A | −0.2686 | 0.9491 | −0.1373 | 0.104* | |
C17 | −0.1083 (7) | 0.8233 (5) | −0.0232 (4) | 0.0714 (12) | |
H17A | −0.0077 | 0.8708 | −0.0490 | 0.086* | |
C18 | −0.1035 (5) | 0.7061 (4) | 0.0676 (3) | 0.0550 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0617 (7) | 0.1274 (11) | 0.0706 (8) | −0.0348 (6) | −0.0137 (5) | −0.0067 (7) |
N1 | 0.0569 (18) | 0.0596 (19) | 0.0461 (18) | −0.0206 (15) | −0.0049 (13) | −0.0116 (16) |
N2 | 0.061 (2) | 0.0602 (19) | 0.0485 (19) | −0.0228 (16) | −0.0107 (14) | −0.0018 (15) |
C1 | 0.051 (2) | 0.055 (2) | 0.046 (2) | −0.0164 (18) | −0.0059 (16) | −0.0075 (18) |
C2 | 0.062 (2) | 0.055 (2) | 0.050 (2) | −0.0259 (19) | −0.0080 (17) | −0.0100 (18) |
C3 | 0.054 (2) | 0.059 (2) | 0.040 (2) | −0.0238 (18) | −0.0067 (15) | −0.0050 (18) |
C4 | 0.0415 (19) | 0.049 (2) | 0.050 (2) | −0.0145 (16) | −0.0058 (15) | −0.0063 (17) |
C5 | 0.052 (2) | 0.061 (2) | 0.053 (2) | −0.0162 (18) | −0.0046 (17) | −0.0050 (19) |
C6 | 0.051 (2) | 0.055 (2) | 0.072 (3) | −0.0130 (18) | −0.0044 (19) | −0.006 (2) |
C7 | 0.066 (3) | 0.049 (2) | 0.077 (3) | −0.014 (2) | −0.007 (2) | −0.016 (2) |
C8 | 0.065 (2) | 0.062 (2) | 0.062 (3) | −0.020 (2) | −0.0022 (19) | −0.022 (2) |
C9 | 0.046 (2) | 0.053 (2) | 0.052 (2) | −0.0165 (17) | −0.0038 (16) | −0.0094 (18) |
C10 | 0.092 (3) | 0.063 (2) | 0.055 (2) | −0.027 (2) | −0.023 (2) | −0.008 (2) |
C11 | 0.085 (3) | 0.058 (3) | 0.092 (3) | −0.016 (2) | −0.014 (3) | 0.005 (2) |
C12 | 0.058 (2) | 0.067 (2) | 0.041 (2) | −0.0226 (19) | −0.0085 (16) | −0.0038 (18) |
C13 | 0.055 (2) | 0.055 (2) | 0.043 (2) | −0.0136 (18) | −0.0064 (17) | −0.0096 (18) |
C14 | 0.066 (3) | 0.081 (3) | 0.068 (3) | −0.019 (2) | −0.024 (2) | −0.003 (2) |
C15 | 0.096 (4) | 0.082 (3) | 0.080 (3) | 0.002 (3) | −0.040 (3) | −0.002 (3) |
C16 | 0.123 (4) | 0.070 (3) | 0.058 (3) | −0.014 (3) | −0.020 (3) | 0.008 (2) |
C17 | 0.091 (3) | 0.070 (3) | 0.050 (2) | −0.033 (2) | 0.006 (2) | −0.004 (2) |
C18 | 0.060 (2) | 0.063 (2) | 0.043 (2) | −0.0200 (19) | −0.0018 (16) | −0.0087 (19) |
Cl1—C18 | 1.738 (4) | C8—C9 | 1.411 (5) |
N1—C1 | 1.321 (4) | C8—H8A | 0.9300 |
N1—C9 | 1.361 (4) | C10—H10A | 0.9600 |
N2—C12 | 1.260 (4) | C10—H10B | 0.9600 |
N2—C13 | 1.413 (4) | C10—H10C | 0.9600 |
C1—C2 | 1.416 (5) | C11—H11A | 0.9600 |
C1—C12 | 1.466 (5) | C11—H11B | 0.9600 |
C2—C3 | 1.355 (5) | C11—H11C | 0.9600 |
C2—H2B | 0.9300 | C12—H12A | 0.9300 |
C3—C4 | 1.418 (4) | C13—C14 | 1.382 (5) |
C3—C10 | 1.505 (5) | C13—C18 | 1.389 (5) |
C4—C5 | 1.408 (5) | C14—C15 | 1.372 (6) |
C4—C9 | 1.427 (5) | C14—H14A | 0.9300 |
C5—C6 | 1.369 (5) | C15—C16 | 1.379 (7) |
C5—H5A | 0.9300 | C15—H15A | 0.9300 |
C6—C7 | 1.405 (5) | C16—C17 | 1.377 (6) |
C6—C11 | 1.512 (5) | C16—H16A | 0.9300 |
C7—C8 | 1.357 (5) | C17—C18 | 1.372 (5) |
C7—H7A | 0.9300 | C17—H17A | 0.9300 |
C1—N1—C9 | 117.8 (3) | H10A—C10—H10B | 109.5 |
C12—N2—C13 | 119.0 (3) | C3—C10—H10C | 109.5 |
N1—C1—C2 | 122.5 (3) | H10A—C10—H10C | 109.5 |
N1—C1—C12 | 115.9 (3) | H10B—C10—H10C | 109.5 |
C2—C1—C12 | 121.6 (3) | C6—C11—H11A | 109.5 |
C3—C2—C1 | 121.3 (3) | C6—C11—H11B | 109.5 |
C3—C2—H2B | 119.4 | H11A—C11—H11B | 109.5 |
C1—C2—H2B | 119.4 | C6—C11—H11C | 109.5 |
C2—C3—C4 | 117.7 (3) | H11A—C11—H11C | 109.5 |
C2—C3—C10 | 120.7 (3) | H11B—C11—H11C | 109.5 |
C4—C3—C10 | 121.7 (3) | N2—C12—C1 | 122.5 (3) |
C5—C4—C3 | 124.0 (3) | N2—C12—H12A | 118.7 |
C5—C4—C9 | 118.0 (3) | C1—C12—H12A | 118.7 |
C3—C4—C9 | 118.0 (3) | C14—C13—C18 | 117.6 (4) |
C6—C5—C4 | 122.4 (4) | C14—C13—N2 | 122.9 (3) |
C6—C5—H5A | 118.8 | C18—C13—N2 | 119.5 (3) |
C4—C5—H5A | 118.8 | C15—C14—C13 | 121.4 (4) |
C5—C6—C7 | 118.5 (4) | C15—C14—H14A | 119.3 |
C5—C6—C11 | 121.2 (4) | C13—C14—H14A | 119.3 |
C7—C6—C11 | 120.3 (4) | C14—C15—C16 | 119.8 (4) |
C8—C7—C6 | 121.5 (3) | C14—C15—H15A | 120.1 |
C8—C7—H7A | 119.2 | C16—C15—H15A | 120.1 |
C6—C7—H7A | 119.2 | C17—C16—C15 | 120.2 (4) |
C7—C8—C9 | 120.7 (4) | C17—C16—H16A | 119.9 |
C7—C8—H8A | 119.6 | C15—C16—H16A | 119.9 |
C9—C8—H8A | 119.6 | C16—C17—C18 | 119.2 (4) |
N1—C9—C8 | 118.4 (3) | C16—C17—H17A | 120.4 |
N1—C9—C4 | 122.7 (3) | C18—C17—H17A | 120.4 |
C8—C9—C4 | 118.9 (3) | C17—C18—C13 | 121.8 (4) |
C3—C10—H10A | 109.5 | C17—C18—Cl1 | 119.1 (3) |
C3—C10—H10B | 109.5 | C13—C18—Cl1 | 119.0 (3) |
C9—N1—C1—C2 | −1.5 (5) | C5—C4—C9—N1 | −178.1 (3) |
C9—N1—C1—C12 | 177.0 (3) | C3—C4—C9—N1 | 1.9 (5) |
N1—C1—C2—C3 | 0.9 (5) | C5—C4—C9—C8 | 0.8 (5) |
C12—C1—C2—C3 | −177.5 (3) | C3—C4—C9—C8 | −179.2 (3) |
C1—C2—C3—C4 | 1.1 (5) | C13—N2—C12—C1 | −178.9 (3) |
C1—C2—C3—C10 | −179.1 (3) | N1—C1—C12—N2 | −169.1 (3) |
C2—C3—C4—C5 | 177.6 (3) | C2—C1—C12—N2 | 9.5 (5) |
C10—C3—C4—C5 | −2.1 (5) | C12—N2—C13—C14 | 54.7 (5) |
C2—C3—C4—C9 | −2.4 (5) | C12—N2—C13—C18 | −129.3 (4) |
C10—C3—C4—C9 | 177.9 (3) | C18—C13—C14—C15 | −1.4 (6) |
C3—C4—C5—C6 | −179.9 (3) | N2—C13—C14—C15 | 174.7 (4) |
C9—C4—C5—C6 | 0.1 (5) | C13—C14—C15—C16 | 1.3 (7) |
C4—C5—C6—C7 | −1.1 (5) | C14—C15—C16—C17 | −0.6 (7) |
C4—C5—C6—C11 | 178.6 (3) | C15—C16—C17—C18 | 0.0 (7) |
C5—C6—C7—C8 | 1.2 (6) | C16—C17—C18—C13 | −0.1 (6) |
C11—C6—C7—C8 | −178.4 (4) | C16—C17—C18—Cl1 | −179.7 (3) |
C6—C7—C8—C9 | −0.3 (6) | C14—C13—C18—C17 | 0.8 (5) |
C1—N1—C9—C8 | −178.8 (3) | N2—C13—C18—C17 | −175.5 (3) |
C1—N1—C9—C4 | 0.1 (5) | C14—C13—C18—Cl1 | −179.6 (3) |
C7—C8—C9—N1 | 178.3 (3) | N2—C13—C18—Cl1 | 4.1 (4) |
C7—C8—C9—C4 | −0.7 (5) |
Experimental details
Crystal data | |
Chemical formula | C18H15ClN2 |
Mr | 294.77 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.4962 (7), 9.5511 (9), 11.4013 (11) |
α, β, γ (°) | 79.039 (2), 76.866 (2), 76.886 (2) |
V (Å3) | 765.90 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.34 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.922, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4930, 3363, 1573 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.217, 0.98 |
No. of reflections | 3363 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.29 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
Cl1—C18 | 1.738 (4) | C2—C3 | 1.355 (5) |
N1—C1 | 1.321 (4) | C3—C10 | 1.505 (5) |
N1—C9 | 1.361 (4) | C6—C11 | 1.512 (5) |
N2—C12 | 1.260 (4) | C7—C8 | 1.357 (5) |
N2—C13 | 1.413 (4) | C13—C14 | 1.382 (5) |
C1—C2 | 1.416 (5) | C13—C18 | 1.389 (5) |
C1—C12 | 1.466 (5) | ||
C1—N1—C9 | 117.8 (3) | C7—C6—C11 | 120.3 (4) |
C12—N2—C13 | 119.0 (3) | N1—C9—C8 | 118.4 (3) |
N1—C1—C2 | 122.5 (3) | N1—C9—C4 | 122.7 (3) |
N1—C1—C12 | 115.9 (3) | N2—C12—C1 | 122.5 (3) |
C2—C1—C12 | 121.6 (3) | C14—C13—C18 | 117.6 (4) |
C2—C3—C10 | 120.7 (3) | C14—C13—N2 | 122.9 (3) |
C4—C3—C10 | 121.7 (3) | C18—C13—N2 | 119.5 (3) |
C5—C4—C3 | 124.0 (3) | C17—C18—Cl1 | 119.1 (3) |
C5—C6—C11 | 121.2 (4) | C13—C18—Cl1 | 119.0 (3) |
C1—C2—C3—C10 | −179.1 (3) | C2—C1—C12—N2 | 9.5 (5) |
C4—C5—C6—C11 | 178.6 (3) | C12—N2—C13—C14 | 54.7 (5) |
C13—N2—C12—C1 | −178.9 (3) | C12—N2—C13—C18 | −129.3 (4) |
N1—C1—C12—N2 | −169.1 (3) | N2—C13—C18—Cl1 | 4.1 (4) |
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Schiff bases, occupying an important place in medicine and industry, are generally useful compounds as starting materials in the preparation of textile, dyestuffs, pesticides and pharmaceuticals, and of compounds that serve as stabilizers and inhibitors in photography (Sommes, 1976). Great attention has been recently begun to concentrate on the compounds obtained from heterocyclic carbaldehydes for the therapy of cancer, the disease of our age (Kouznetsov et al., 1998; Öcal & Kaban, 1998). Hence, in our research, new Schiff bases containing different functional groups have been synthesized for the purpose of making some contributions to that class of substances which are now being tried as anticancer reagents.
This structure of the title compound, 4,6-Dimethylquinoline-2-[N-(o-chlorophenyl)formimidoyl], (I), is isomorphous with 4,6-dimethylquinoline-2-[N-(o-tolyl)formimidoyl], (II) (Akkurt et al., 2001). The quinoline and phenyl rings are planar. In the quinoline ring, the C3—C4—C5 angle is bigger than 120° [124.0 (3)°] and the N1—C9—C8 angle is smaller than 120° [118.4 (3)°]. Corresponding values are almostly comparable with the ones in 3-(p-chlorophenyl)-5-methyl-2-(8-quinolinyl)-4-thiazolidinone (Öztürk et al., 2000) [for molecule A of two independent molecules in the asymmetric unit, 122.8 (6) and 120.3 (5)°, respectively, and for the molecule B, 124.4 (7) and 117.4 (4)°, respectively] and in (II) [123.4 (2) and 118.2 (2)°, respectively]. The fold angles between the least-squares planes of the quinoline and phenyl rings are 116.2 (1) and 118.5 (1)° in (II) and 61.8 (1)° in N-8-azanaphtylmethylene-4-chloroaniline (Öztürk et al., 2001). This large deviation is possibly due to the steric factors which occur the different position of the Cl atom in the phenyl ring. There are non-bonded contacts > 3.3 Å between non-H atoms.