Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006705/bt6038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006705/bt6038Isup2.hkl |
CCDC reference: 165668
The title compound was synthesized by the condensation of 4,6-dimethylquinoline-2-carbaldehyde with o-toluidine in dry ethanol for 6.5 h. Light-yellow crystals were obtained after crystallization from ethanol. Yield: 54%; m.p.: 392 K; IR (KBr): γ 3040, 2890, 1585 cm-1; 1H NMR (CDCl3, δ, 200 MHz): 2.46 (3H, s, o-CH3), 2.59 (3H, s, 6-CH3), 2.76 (3H, s, 4-CH3), 7.05–8.64 (9H, m, ArH and CH) p.p.m.; UV (CHCl3): λmax 260.8, 312.5 nm. Elemental analysis, C19H18N2 requires: C 83.18, H 6.61, N 10.21%; found: C 83.14, H 6.58, N 10.11% (Aydo~gan, 1993).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976).
Fig. 1. An ORTEPII drawing of the molecular structure of (I) showing the labelling of the non-H atoms. Anisotropic displacement ellipsoids are shown at the 50% probability level. |
C19H18N2 | Z = 2 |
Mr = 274.37 | F(000) = 294 |
Triclinic, P1 | Dx = 1.180 Mg m−3 |
a = 7.5693 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5620 (9) Å | Cell parameters from 1739 reflections |
c = 11.3908 (11) Å | θ = 3.1–27.5° |
α = 79.203 (2)° | µ = 0.07 mm−1 |
β = 76.735 (2)° | T = 293 K |
γ = 77.514 (2)° | Needle, colourless |
V = 775.19 (13) Å3 | 0.44 × 0.26 × 0.06 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 1697 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −9→9 |
5000 measured reflections | k = −12→12 |
3414 independent reflections | l = −14→14 |
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)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.236 | w = 1/[σ2(Fo2) + (0.1124P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3414 reflections | Δρmax = 0.24 e Å−3 |
194 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL93, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.023 (9) |
C19H18N2 | γ = 77.514 (2)° |
Mr = 274.37 | V = 775.19 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5693 (7) Å | Mo Kα radiation |
b = 9.5620 (9) Å | µ = 0.07 mm−1 |
c = 11.3908 (11) Å | T = 293 K |
α = 79.203 (2)° | 0.44 × 0.26 × 0.06 mm |
β = 76.735 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 1697 reflections with I > 2σ(I) |
5000 measured reflections | Rint = 0.035 |
3414 independent reflections |
R[F2 > 2σ(F2)] = 0.073 | 0 restraints |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.24 e Å−3 |
3414 reflections | Δρmin = −0.27 e Å−3 |
194 parameters |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor-obs 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 | ||
N1 | 0.2160 (3) | 0.1467 (2) | 0.2710 (2) | 0.0529 (6) | |
N2 | 0.2614 (3) | 0.5139 (2) | 0.2097 (2) | 0.0544 (6) | |
C1 | 0.2282 (4) | 0.2707 (3) | 0.2999 (2) | 0.0504 (7) | |
C2 | 0.2442 (4) | 0.2870 (3) | 0.4167 (2) | 0.0531 (7) | |
H2B | 0.2493 | 0.3779 | 0.4326 | 0.064* | |
C3 | 0.2524 (4) | 0.1713 (3) | 0.5074 (2) | 0.0504 (7) | |
C4 | 0.2448 (3) | 0.0344 (3) | 0.4775 (2) | 0.0463 (6) | |
C5 | 0.2588 (4) | −0.0961 (3) | 0.5607 (3) | 0.0566 (7) | |
H5A | 0.2738 | −0.0940 | 0.6391 | 0.068* | |
C6 | 0.2507 (4) | −0.2254 (3) | 0.5284 (3) | 0.0604 (8) | |
C7 | 0.2279 (4) | −0.2278 (3) | 0.4103 (3) | 0.0641 (8) | |
H7A | 0.2215 | −0.3151 | 0.3882 | 0.077* | |
C8 | 0.2148 (4) | −0.1058 (3) | 0.3274 (3) | 0.0594 (8) | |
H8A | 0.1982 | −0.1103 | 0.2499 | 0.071* | |
C9 | 0.2263 (4) | 0.0276 (3) | 0.3581 (2) | 0.0494 (7) | |
C10 | 0.2665 (5) | 0.1883 (3) | 0.6327 (3) | 0.0649 (9) | |
H10A | 0.3793 | 0.1303 | 0.6522 | 0.097* | |
H10B | 0.1635 | 0.1573 | 0.6907 | 0.097* | |
H10C | 0.2657 | 0.2881 | 0.6356 | 0.097* | |
C11 | 0.2706 (5) | −0.3633 (3) | 0.6187 (4) | 0.0832 (11) | |
H11A | 0.1772 | −0.4169 | 0.6183 | 0.125* | |
H11B | 0.2569 | −0.3394 | 0.6989 | 0.125* | |
H11C | 0.3903 | −0.4209 | 0.5961 | 0.125* | |
C12 | 0.2241 (4) | 0.3936 (3) | 0.2010 (3) | 0.0556 (7) | |
H12A | 0.1930 | 0.3828 | 0.1293 | 0.067* | |
C13 | 0.2501 (4) | 0.6284 (3) | 0.1108 (2) | 0.0514 (7) | |
C14 | 0.0932 (5) | 0.6723 (3) | 0.0603 (3) | 0.0696 (9) | |
H14A | −0.0047 | 0.6224 | 0.0885 | 0.083* | |
C15 | 0.0804 (6) | 0.7884 (4) | −0.0307 (3) | 0.0859 (11) | |
H15A | −0.0250 | 0.8171 | −0.0642 | 0.103* | |
C16 | 0.2257 (6) | 0.8616 (4) | −0.0716 (3) | 0.0853 (12) | |
H16A | 0.2185 | 0.9401 | −0.1334 | 0.102* | |
C17 | 0.3818 (5) | 0.8196 (3) | −0.0218 (3) | 0.0724 (9) | |
H17A | 0.4786 | 0.8705 | −0.0504 | 0.087* | |
C18 | 0.3972 (4) | 0.7027 (3) | 0.0705 (2) | 0.0549 (7) | |
C19 | 0.5668 (5) | 0.6568 (4) | 0.1253 (3) | 0.0773 (10) | |
H19A | 0.6451 | 0.7278 | 0.0960 | 0.116* | |
H19B | 0.6322 | 0.5650 | 0.1024 | 0.116* | |
H19C | 0.5317 | 0.6483 | 0.2125 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.061 (2) | 0.0579 (14) | 0.0441 (12) | −0.0158 (11) | −0.0143 (10) | −0.0078 (11) |
N2 | 0.061 (2) | 0.0510 (13) | 0.0520 (13) | −0.0140 (11) | −0.0165 (11) | 0.0016 (11) |
C1 | 0.052 (2) | 0.049 (2) | 0.053 (2) | −0.0121 (12) | −0.0143 (13) | −0.0062 (13) |
C2 | 0.062 (2) | 0.0454 (15) | 0.057 (2) | −0.0178 (13) | −0.0171 (13) | −0.0053 (14) |
C3 | 0.052 (2) | 0.051 (2) | 0.052 (2) | −0.0145 (12) | −0.0133 (12) | −0.0064 (13) |
C4 | 0.0426 (15) | 0.0440 (14) | 0.053 (2) | −0.0101 (11) | −0.0101 (12) | −0.0041 (13) |
C5 | 0.059 (2) | 0.050 (2) | 0.059 (2) | −0.0092 (13) | −0.0149 (14) | 0.0000 (14) |
C6 | 0.056 (2) | 0.045 (2) | 0.075 (2) | −0.0076 (13) | −0.0081 (15) | −0.0040 (15) |
C7 | 0.065 (2) | 0.045 (2) | 0.085 (2) | −0.0112 (14) | −0.011 (2) | −0.017 (2) |
C8 | 0.061 (2) | 0.057 (2) | 0.064 (2) | −0.0143 (14) | −0.0119 (14) | −0.017 (2) |
C9 | 0.046 (2) | 0.0477 (15) | 0.056 (2) | −0.0100 (12) | −0.0100 (12) | −0.0080 (13) |
C10 | 0.088 (2) | 0.057 (2) | 0.056 (2) | −0.021 (2) | −0.024 (2) | −0.0058 (15) |
C11 | 0.086 (3) | 0.050 (2) | 0.105 (3) | −0.010 (2) | −0.017 (2) | 0.005 (2) |
C12 | 0.063 (2) | 0.058 (2) | 0.049 (2) | −0.0120 (14) | −0.0172 (13) | −0.0045 (14) |
C13 | 0.064 (2) | 0.0474 (15) | 0.0455 (15) | −0.0115 (13) | −0.0170 (13) | −0.0036 (13) |
C14 | 0.074 (2) | 0.066 (2) | 0.074 (2) | −0.017 (2) | −0.031 (2) | 0.002 (2) |
C15 | 0.100 (3) | 0.074 (2) | 0.087 (2) | −0.007 (2) | −0.050 (2) | 0.009 (2) |
C16 | 0.126 (3) | 0.062 (2) | 0.061 (2) | −0.013 (2) | −0.028 (2) | 0.014 (2) |
C17 | 0.094 (3) | 0.064 (2) | 0.057 (2) | −0.026 (2) | −0.007 (2) | −0.001 (2) |
C18 | 0.067 (2) | 0.053 (2) | 0.0457 (15) | −0.0158 (14) | −0.0092 (13) | −0.0050 (13) |
C19 | 0.068 (2) | 0.093 (2) | 0.074 (2) | −0.025 (2) | −0.016 (2) | −0.006 (2) |
N1—C1 | 1.316 (3) | C10—H10B | 0.96 |
N1—C9 | 1.364 (3) | C10—H10C | 0.96 |
N2—C12 | 1.267 (3) | C11—H11A | 0.96 |
N2—C13 | 1.420 (3) | C11—H11B | 0.96 |
C1—C2 | 1.403 (4) | C11—H11C | 0.96 |
C1—C12 | 1.468 (4) | C12—H12A | 0.93 |
C2—C3 | 1.366 (3) | C13—C14 | 1.388 (4) |
C2—H2B | 0.93 | C13—C18 | 1.393 (4) |
C3—C4 | 1.429 (3) | C14—C15 | 1.373 (4) |
C3—C10 | 1.496 (4) | C14—H14A | 0.93 |
C4—C9 | 1.413 (4) | C15—C16 | 1.376 (5) |
C4—C5 | 1.419 (3) | C15—H15A | 0.93 |
C5—C6 | 1.371 (4) | C16—C17 | 1.377 (5) |
C5—H5A | 0.93 | C16—H16A | 0.93 |
C6—C7 | 1.400 (4) | C17—C18 | 1.388 (4) |
C6—C11 | 1.515 (4) | C17—H17A | 0.93 |
C7—C8 | 1.357 (4) | C18—C19 | 1.501 (4) |
C7—H7A | 0.93 | C19—H19A | 0.96 |
C8—C9 | 1.410 (4) | C19—H19B | 0.96 |
C8—H8A | 0.93 | C19—H19C | 0.96 |
C10—H10A | 0.96 | ||
C1—N1—C9 | 118.0 (2) | H10B—C10—H10C | 109.5 |
C12—N2—C13 | 119.0 (2) | C6—C11—H11A | 109.5 (2) |
N1—C1—C2 | 123.2 (3) | C6—C11—H11B | 109.5 (2) |
N1—C1—C12 | 115.5 (2) | H11A—C11—H11B | 109.5 |
C2—C1—C12 | 121.3 (2) | C6—C11—H11C | 109.5 (2) |
C3—C2—C1 | 120.9 (2) | H11A—C11—H11C | 109.5 |
C3—C2—H2B | 119.6 (2) | H11B—C11—H11C | 109.5 |
C1—C2—H2B | 119.6 (2) | N2—C12—C1 | 122.5 (3) |
C2—C3—C4 | 117.0 (2) | N2—C12—H12A | 118.7 (2) |
C2—C3—C10 | 121.2 (2) | C1—C12—H12A | 118.7 (2) |
C4—C3—C10 | 121.8 (2) | C14—C13—C18 | 120.3 (3) |
C9—C4—C5 | 118.1 (2) | C14—C13—N2 | 121.6 (3) |
C9—C4—C3 | 118.5 (2) | C18—C13—N2 | 118.0 (2) |
C5—C4—C3 | 123.4 (2) | C15—C14—C13 | 120.8 (3) |
C6—C5—C4 | 121.6 (3) | C15—C14—H14A | 119.6 (2) |
C6—C5—H5A | 119.2 (2) | C13—C14—H14A | 119.6 (2) |
C4—C5—H5A | 119.2 (2) | C14—C15—C16 | 119.1 (3) |
C5—C6—C7 | 118.9 (3) | C14—C15—H15A | 120.4 (2) |
C5—C6—C11 | 120.2 (3) | C16—C15—H15A | 120.4 (2) |
C7—C6—C11 | 120.9 (3) | C15—C16—C17 | 120.6 (3) |
C8—C7—C6 | 121.6 (3) | C15—C16—H16A | 119.7 (2) |
C8—C7—H7A | 119.2 (2) | C17—C16—H16A | 119.7 (2) |
C6—C7—H7A | 119.2 (2) | C16—C17—C18 | 121.2 (3) |
C7—C8—C9 | 120.3 (3) | C16—C17—H17A | 119.4 (2) |
C7—C8—H8A | 119.8 (2) | C18—C17—H17A | 119.4 (2) |
C9—C8—H8A | 119.8 (2) | C17—C18—C13 | 117.9 (3) |
N1—C9—C8 | 118.2 (2) | C17—C18—C19 | 121.3 (3) |
N1—C9—C4 | 122.3 (2) | C13—C18—C19 | 120.7 (3) |
C8—C9—C4 | 119.5 (3) | C18—C19—H19A | 109.5 (2) |
C3—C10—H10A | 109.5 (2) | C18—C19—H19B | 109.5 (2) |
C3—C10—H10B | 109.5 (2) | H19A—C19—H19B | 109.5 |
H10A—C10—H10B | 109.5 | C18—C19—H19C | 109.5 (2) |
C3—C10—H10C | 109.5 (2) | H19A—C19—H19C | 109.5 |
H10A—C10—H10C | 109.5 | H19B—C19—H19C | 109.5 |
C9—N1—C1—C2 | −2.5 (4) | C5—C4—C9—N1 | −178.5 (2) |
C9—N1—C1—C12 | 177.5 (2) | C3—C4—C9—N1 | 0.2 (4) |
N1—C1—C2—C3 | 1.6 (4) | C5—C4—C9—C8 | 2.6 (4) |
C12—C1—C2—C3 | −178.4 (3) | C3—C4—C9—C8 | −178.7 (2) |
C1—C2—C3—C4 | 0.3 (4) | C13—N2—C12—C1 | −178.6 (2) |
C1—C2—C3—C10 | −179.1 (3) | N1—C1—C12—N2 | −169.4 (3) |
C2—C3—C4—C9 | −1.1 (4) | C2—C1—C12—N2 | 10.6 (4) |
C10—C3—C4—C9 | 178.3 (3) | C12—N2—C13—C14 | 52.1 (4) |
C2—C3—C4—C5 | 177.5 (3) | C12—N2—C13—C18 | −132.1 (3) |
C10—C3—C4—C5 | −3.1 (4) | C18—C13—C14—C15 | 0.6 (5) |
C9—C4—C5—C6 | −1.4 (4) | N2—C13—C14—C15 | 176.3 (3) |
C3—C4—C5—C6 | 179.9 (3) | C13—C14—C15—C16 | −0.1 (5) |
C4—C5—C6—C7 | −0.1 (4) | C14—C15—C16—C17 | −0.3 (5) |
C4—C5—C6—C11 | 178.5 (3) | C15—C16—C17—C18 | 0.2 (5) |
C5—C6—C7—C8 | 0.4 (5) | C16—C17—C18—C13 | 0.3 (4) |
C11—C6—C7—C8 | −178.2 (3) | C16—C17—C18—C19 | −179.8 (3) |
C6—C7—C8—C9 | 0.8 (5) | C14—C13—C18—C17 | −0.7 (4) |
C1—N1—C9—C8 | −179.5 (2) | N2—C13—C18—C17 | −176.6 (3) |
C1—N1—C9—C4 | 1.6 (4) | C14—C13—C18—C19 | 179.4 (3) |
C7—C8—C9—N1 | 178.7 (3) | N2—C13—C18—C19 | 3.6 (4) |
C7—C8—C9—C4 | −2.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C19H18N2 |
Mr | 274.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5693 (7), 9.5620 (9), 11.3908 (11) |
α, β, γ (°) | 79.203 (2), 76.735 (2), 77.514 (2) |
V (Å3) | 775.19 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.44 × 0.26 × 0.06 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5000, 3414, 1697 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.236, 1.02 |
No. of reflections | 3414 |
No. of parameters | 194 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), ORTEPII (Johnson, 1976).
N1—C1 | 1.316 (3) | C3—C10 | 1.496 (4) |
N1—C9 | 1.364 (3) | C6—C11 | 1.515 (4) |
N2—C12 | 1.267 (3) | C18—C19 | 1.501 (4) |
N2—C13 | 1.420 (3) | ||
C1—N1—C9 | 118.0 (2) | C5—C6—C11 | 120.2 (3) |
C12—N2—C13 | 119.0 (2) | C7—C6—C11 | 120.9 (3) |
C2—C3—C10 | 121.2 (2) | N1—C9—C8 | 118.2 (2) |
C4—C3—C10 | 121.8 (2) | C17—C18—C19 | 121.3 (3) |
C5—C4—C3 | 123.4 (2) | C13—C18—C19 | 120.7 (3) |
C13—N2—C12—C1 | −178.6 (2) |
Interest in quinoxaline derivatives has increased greatly during recent years due to their different applications in various areas. Some derivatives are used as colorimetric agents (Campaigne & McLaughlin, 1983), antibacterial agents (Boutti & Lecolier,1976) and colouring matter. Other derivatives possess various biological activities (De Clercq, 1998; Li et al., 1997). Much attention has recently begun to concentrate on compounds obtained from heterocyclic carbaldehydes for the treatment of cancer (Kouznetsov et al., 1998; Öcal & Kaban, 1998). The structure of 4,6-Dimethyl-2-(o-tolyliminomethyl)quinoline, (I), has beed determined and is presented here.
The quinoline and phenyl rings are planar. In the quinoline ring, the angle C3—C4—C5 is greater than 120° [123.4 (2)°] and the angle C8—C9—N1 is smaller than 120° [118.2 (2)°] (Öztürk et al., 2000). The dihedral angle between the least-squares planes of the quinoline and phenyl rings is 118.5 (1)°.