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The mol­ecule of the title compound, C20H20N2, is not planar. The dihedral angle between the planes of the quinoline and phenyl rings is 64.6 (1)°, and these two planes make angles of 17.7 (2) and 47.7 (3)°, respectively, with the plane of the central imino­methyl moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000788/cv6081sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000788/cv6081Isup2.hkl
Contains datablock I

CCDC reference: 180792

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.063
  • wR factor = 0.190
  • Data-to-parameter ratio = 15.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

4,6-Dimethylquinoline-2-[N-(2,4-dimethylphenyl)formimidoyl] top
Crystal data top
C20H20N2Z = 2
Mr = 288.38F(000) = 308
Triclinic, P1Dx = 1.175 Mg m3
a = 7.4939 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6449 (8) ÅCell parameters from 2189 reflections
c = 12.1632 (9) Åθ = 2.7–27.5°
α = 84.559 (2)°µ = 0.07 mm1
β = 84.522 (2)°T = 293 K
γ = 68.944 (2)°Needle, colorless
V = 814.95 (11) Å30.42 × 0.30 × 0.08 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
Detector resolution: 8.33 pixels mm-1h = 99
ω scansk = 1212
5288 measured reflectionsl = 1015
3600 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0792P)2 + 0.1802P]
where P = (Fo2 + 2Fc2)/3
3600 reflections(Δ/σ)max = 0.003
235 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

Experimental. The data was collected by using a Siemens SMART 1000 CCD area-detector diffractometer and graphite monochromator. The structure was solved by direct methods and refined by full-matrix least-squares technique.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7090 (3)0.1756 (2)0.25376 (15)0.0533 (5)
N20.7675 (3)0.5216 (2)0.20649 (15)0.0550 (5)
C10.7143 (3)0.3018 (3)0.28407 (18)0.0497 (5)
C20.7217 (3)0.3300 (3)0.39523 (18)0.0496 (5)
C30.7306 (3)0.2230 (3)0.47835 (18)0.0493 (5)
C40.7350 (3)0.0816 (2)0.44846 (17)0.0458 (5)
C50.7537 (3)0.0413 (3)0.5249 (2)0.0533 (6)
C60.7571 (3)0.1752 (3)0.4936 (2)0.0566 (6)
C70.7408 (4)0.1890 (3)0.3809 (2)0.0607 (7)
C80.7225 (4)0.0733 (3)0.3042 (2)0.0583 (6)
C90.7217 (3)0.0642 (2)0.33519 (18)0.0478 (5)
C100.7369 (4)0.2512 (3)0.59708 (19)0.0618 (7)
H10A0.73580.35040.60130.093*
H10B0.85170.18090.62650.093*
H10C0.62710.24050.63930.093*
C110.7802 (4)0.3062 (3)0.5773 (2)0.0735 (8)
H11A0.77520.27460.65040.110*
H11B0.90140.38330.56200.110*
H11C0.67870.34350.57250.110*
C120.7170 (3)0.4135 (3)0.19309 (19)0.0535 (6)
C130.7711 (4)0.6248 (3)0.11542 (18)0.0529 (6)
C140.6163 (4)0.6895 (3)0.0497 (2)0.0660 (7)
C150.6192 (5)0.7954 (3)0.0348 (2)0.0730 (8)
C160.7759 (4)0.8393 (3)0.0558 (2)0.0649 (7)
C170.9302 (4)0.7736 (3)0.0097 (2)0.0609 (7)
C180.9312 (4)0.6672 (3)0.09544 (18)0.0532 (6)
C191.1028 (4)0.5964 (3)0.1631 (2)0.0740 (8)
H19A1.17330.49790.14010.111*
H19B1.06110.59090.23990.111*
H19C1.18350.65520.15240.111*
C200.7820 (5)0.9555 (4)0.1475 (3)0.0958 (11)
H20A0.66080.99520.18020.144*
H20B0.88120.91070.20280.144*
H20C0.80801.03440.11750.144*
H20.718 (3)0.426 (3)0.4115 (17)0.054 (6)*
H50.767 (3)0.032 (2)0.6013 (19)0.051 (6)*
H70.741 (4)0.279 (3)0.360 (2)0.073 (8)*
H80.716 (4)0.083 (3)0.223 (2)0.065 (7)*
H120.684 (3)0.394 (3)0.118 (2)0.061 (7)*
H150.501 (4)0.663 (3)0.067 (2)0.069 (7)*
H160.504 (5)0.838 (3)0.081 (2)0.095 (10)*
H181.044 (4)0.802 (3)0.003 (2)0.078 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0576 (12)0.0546 (12)0.0529 (11)0.0256 (10)0.0008 (9)0.0084 (9)
N20.0658 (13)0.0530 (12)0.0504 (11)0.0270 (10)0.0014 (9)0.0022 (9)
C10.0483 (13)0.0528 (13)0.0521 (13)0.0227 (11)0.0008 (10)0.0057 (10)
C20.0565 (14)0.0464 (13)0.0527 (13)0.0256 (11)0.0023 (10)0.0071 (10)
C30.0448 (13)0.0556 (14)0.0530 (13)0.0233 (11)0.0038 (10)0.0076 (11)
C40.0401 (12)0.0476 (12)0.0524 (12)0.0188 (10)0.0008 (9)0.0047 (10)
C50.0475 (13)0.0565 (14)0.0578 (14)0.0215 (11)0.0037 (11)0.0007 (11)
C60.0437 (13)0.0509 (14)0.0763 (16)0.0197 (11)0.0002 (11)0.0015 (12)
C70.0548 (15)0.0481 (14)0.0839 (18)0.0227 (12)0.0018 (12)0.0152 (13)
C80.0580 (15)0.0565 (15)0.0660 (16)0.0251 (12)0.0002 (12)0.0152 (12)
C90.0438 (12)0.0500 (13)0.0536 (12)0.0209 (11)0.0019 (9)0.0071 (10)
C100.0761 (17)0.0659 (16)0.0529 (14)0.0347 (14)0.0067 (12)0.0080 (12)
C110.0629 (17)0.0545 (16)0.101 (2)0.0221 (14)0.0043 (15)0.0090 (15)
C120.0572 (14)0.0562 (14)0.0495 (13)0.0228 (12)0.0029 (11)0.0046 (11)
C130.0652 (15)0.0524 (14)0.0450 (12)0.0261 (12)0.0022 (11)0.0066 (10)
C140.0662 (18)0.0701 (18)0.0663 (16)0.0310 (15)0.0067 (13)0.0029 (13)
C150.078 (2)0.0729 (19)0.0627 (16)0.0213 (16)0.0099 (14)0.0072 (14)
C160.0807 (19)0.0568 (15)0.0499 (13)0.0197 (14)0.0103 (13)0.0010 (11)
C170.0704 (17)0.0611 (16)0.0542 (14)0.0294 (14)0.0116 (12)0.0083 (12)
C180.0634 (15)0.0522 (13)0.0460 (12)0.0228 (12)0.0033 (10)0.0095 (10)
C190.0692 (18)0.087 (2)0.0704 (17)0.0342 (16)0.0084 (14)0.0031 (15)
C200.113 (3)0.087 (2)0.074 (2)0.028 (2)0.0066 (18)0.0216 (17)
Geometric parameters (Å, º) top
N1—C11.320 (3)C10—H10C0.9600
N1—C91.373 (3)C11—H11A0.9600
N2—C121.259 (3)C11—H11B0.9600
N2—C131.423 (3)C11—H11C0.9600
C1—C21.414 (3)C12—H121.03 (2)
C1—C121.473 (3)C13—C141.392 (3)
C2—C31.363 (3)C13—C181.394 (3)
C2—H20.95 (2)C14—C151.383 (4)
C3—C41.432 (3)C14—H150.99 (3)
C3—C101.503 (3)C15—C161.380 (4)
C4—C51.409 (3)C15—H161.01 (3)
C4—C91.421 (3)C16—C171.387 (4)
C5—C61.372 (3)C16—C201.514 (3)
C5—H50.96 (2)C17—C181.391 (3)
C6—C71.410 (4)C17—H180.98 (3)
C6—C111.515 (3)C18—C191.504 (3)
C7—C81.361 (4)C19—H19A0.9600
C7—H70.93 (3)C19—H19B0.9600
C8—C91.410 (3)C19—H19C0.9600
C8—H81.01 (2)C20—H20A0.9600
C10—H10A0.9600C20—H20B0.9600
C10—H10B0.9600C20—H20C0.9600
C1—N1—C9117.2 (2)H11A—C11—H11B109.5
C12—N2—C13119.4 (2)C6—C11—H11C109.5
N1—C1—C2123.6 (2)H11A—C11—H11C109.5
N1—C1—C12115.4 (2)H11B—C11—H11C109.5
C2—C1—C12121.0 (2)N2—C12—C1121.6 (2)
C3—C2—C1120.6 (2)N2—C12—H12122.2 (13)
C3—C2—H2120.3 (13)C1—C12—H12116.0 (13)
C1—C2—H2119.0 (13)C14—C13—C18119.5 (2)
C2—C3—C4117.6 (2)C14—C13—N2121.9 (2)
C2—C3—C10121.4 (2)C18—C13—N2118.6 (2)
C4—C3—C10121.0 (2)C15—C14—C13120.8 (3)
C5—C4—C9118.3 (2)C15—C14—H15120.4 (15)
C5—C4—C3123.6 (2)C13—C14—H15118.7 (14)
C9—C4—C3118.04 (19)C16—C15—C14120.7 (3)
C6—C5—C4122.2 (2)C16—C15—H16121.4 (17)
C6—C5—H5118.8 (13)C14—C15—H16118.0 (17)
C4—C5—H5119.0 (13)C15—C16—C17118.1 (2)
C5—C6—C7118.4 (2)C15—C16—C20121.6 (3)
C5—C6—C11121.1 (2)C17—C16—C20120.3 (3)
C7—C6—C11120.5 (2)C16—C17—C18122.5 (2)
C8—C7—C6121.4 (2)C16—C17—H18120.2 (15)
C8—C7—H7120.1 (16)C18—C17—H18117.2 (15)
C6—C7—H7118.5 (16)C17—C18—C13118.4 (2)
C7—C8—C9120.7 (2)C17—C18—C19120.9 (2)
C7—C8—H8121.8 (14)C13—C18—C19120.7 (2)
C9—C8—H8117.4 (14)C18—C19—H19A109.5
N1—C9—C8118.2 (2)C18—C19—H19B109.5
N1—C9—C4122.85 (19)H19A—C19—H19B109.5
C8—C9—C4119.0 (2)C18—C19—H19C109.5
C3—C10—H10A109.5H19A—C19—H19C109.5
C3—C10—H10B109.5H19B—C19—H19C109.5
H10A—C10—H10B109.5C16—C20—H20A109.5
C3—C10—H10C109.5C16—C20—H20B109.5
H10A—C10—H10C109.5H20A—C20—H20B109.5
H10B—C10—H10C109.5C16—C20—H20C109.5
C6—C11—H11A109.5H20A—C20—H20C109.5
C6—C11—H11B109.5H20B—C20—H20C109.5
 

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