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In the title compound, C20H14N2, the orientations of the three aromatic rings are determined by the sp2 state of the two central N and C atoms. The crystal packing of the title compound is stabilized by weak C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011066/cv6121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011066/cv6121Isup2.hkl
Contains datablock I

CCDC reference: 189916

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.059
  • wR factor = 0.139
  • Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.101 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(19) - C(20) = 1.44 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

2-Cyano-N-diphenylmethylenebenzenamine top
Crystal data top
C20H14N2F(000) = 592
Mr = 282.33Dx = 1.233 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.3429 (3) ÅCell parameters from 2721 reflections
b = 15.8543 (2) Åθ = 2.6–28.3°
c = 10.6022 (3) ŵ = 0.07 mm1
β = 104.45 (3)°T = 213 K
V = 1520.8 (2) Å3Slab, colorless
Z = 40.32 × 0.22 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1539 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.102
Graphite monochromatorθmax = 28.3°, θmin = 2.6°
Detector resolution: 8.33 pixels mm-1h = 1212
ω scansk = 2016
8637 measured reflectionsl = 1312
3625 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0345P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.81(Δ/σ)max < 0.001
3625 reflectionsΔρmax = 0.24 e Å3
200 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (3)
Special details top

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 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2885 (2)0.09522 (11)0.04620 (17)0.0302 (5)
C200.1070 (3)0.21491 (14)0.1201 (2)0.0353 (6)
C10.2486 (3)0.05998 (16)0.2188 (2)0.0353 (6)
H10.28170.11350.18940.042*
C20.2123 (3)0.04245 (17)0.3507 (2)0.0480 (7)
H20.22140.08410.41000.058*
C30.1627 (3)0.03669 (18)0.3943 (3)0.0498 (8)
H30.13760.04800.48320.060*
C40.1497 (3)0.09916 (17)0.3082 (2)0.0448 (7)
H40.11720.15270.33820.054*
C50.1858 (3)0.08158 (14)0.1760 (2)0.0350 (6)
H50.17640.12360.11740.042*
C60.2355 (2)0.00264 (13)0.1299 (2)0.0248 (5)
C70.2677 (2)0.01782 (13)0.0121 (2)0.0246 (5)
C80.2653 (2)0.05309 (13)0.1050 (2)0.0249 (5)
C90.1588 (3)0.05495 (15)0.1758 (2)0.0351 (6)
H90.08870.01220.16540.042*
C100.1569 (3)0.12035 (16)0.2620 (2)0.0429 (7)
H100.08380.12230.30750.052*
C110.2625 (3)0.18232 (17)0.2802 (2)0.0466 (7)
H110.26280.22510.34020.056*
C120.3672 (3)0.18141 (15)0.2105 (2)0.0445 (7)
H120.43820.22380.22320.053*
C130.3686 (3)0.11760 (14)0.1208 (2)0.0328 (6)
H130.43830.11820.07170.039*
C140.3207 (3)0.11934 (14)0.1793 (2)0.0281 (5)
C150.4428 (3)0.08998 (14)0.2726 (2)0.0366 (6)
H150.50570.05050.24990.044*
C160.4708 (3)0.11956 (16)0.3992 (2)0.0439 (7)
H160.55270.09950.46100.053*
C170.3796 (3)0.17813 (16)0.4355 (2)0.0452 (7)
H170.39950.19710.52110.054*
C180.2588 (3)0.20844 (15)0.3442 (2)0.0394 (7)
H180.19610.24750.36820.047*
C190.2309 (3)0.18042 (13)0.2158 (2)0.0283 (5)
N20.0089 (3)0.24445 (14)0.0470 (2)0.0504 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0392 (12)0.0286 (11)0.0243 (11)0.0013 (9)0.0108 (9)0.0044 (8)
C200.0492 (17)0.0284 (14)0.0353 (15)0.0008 (12)0.0239 (13)0.0012 (11)
C10.0393 (15)0.0357 (14)0.0315 (14)0.0060 (11)0.0100 (11)0.0009 (11)
C20.0624 (19)0.0529 (19)0.0284 (15)0.0180 (15)0.0110 (13)0.0097 (12)
C30.0530 (19)0.063 (2)0.0273 (15)0.0171 (15)0.0009 (13)0.0106 (14)
C40.0454 (17)0.0479 (17)0.0365 (16)0.0041 (13)0.0014 (12)0.0158 (13)
C50.0363 (15)0.0371 (15)0.0298 (14)0.0026 (11)0.0049 (11)0.0033 (10)
C60.0243 (12)0.0278 (13)0.0235 (12)0.0055 (10)0.0081 (9)0.0018 (9)
C70.0223 (13)0.0269 (13)0.0273 (13)0.0033 (10)0.0111 (9)0.0005 (10)
C80.0269 (13)0.0239 (13)0.0254 (12)0.0028 (10)0.0092 (10)0.0068 (9)
C90.0334 (15)0.0386 (15)0.0378 (15)0.0042 (11)0.0173 (11)0.0058 (11)
C100.0569 (19)0.0453 (17)0.0339 (15)0.0203 (14)0.0251 (13)0.0109 (12)
C110.072 (2)0.0383 (17)0.0294 (15)0.0132 (15)0.0118 (14)0.0037 (11)
C120.0574 (19)0.0344 (16)0.0394 (16)0.0049 (13)0.0078 (14)0.0033 (12)
C130.0349 (15)0.0345 (15)0.0319 (14)0.0019 (11)0.0139 (11)0.0007 (11)
C140.0385 (15)0.0247 (13)0.0234 (12)0.0047 (10)0.0120 (10)0.0034 (9)
C150.0385 (15)0.0392 (15)0.0334 (15)0.0000 (12)0.0117 (12)0.0053 (11)
C160.0490 (18)0.0517 (18)0.0289 (15)0.0013 (13)0.0059 (12)0.0051 (12)
C170.062 (2)0.0487 (17)0.0268 (15)0.0052 (14)0.0153 (13)0.0069 (12)
C180.0553 (18)0.0350 (15)0.0355 (15)0.0013 (12)0.0256 (13)0.0039 (11)
C190.0408 (15)0.0246 (13)0.0241 (13)0.0026 (11)0.0169 (11)0.0002 (10)
N20.0586 (16)0.0520 (15)0.0429 (14)0.0144 (12)0.0173 (12)0.0073 (11)
Geometric parameters (Å, º) top
N1—C71.280 (2)C9—C101.385 (3)
N1—C141.420 (3)C9—H90.9300
C20—N21.143 (3)C10—C111.372 (4)
C20—C191.443 (4)C10—H100.9300
C1—C21.383 (3)C11—C121.365 (4)
C1—C61.395 (3)C11—H110.9300
C1—H10.9300C12—C131.391 (3)
C2—C31.377 (3)C12—H120.9300
C2—H20.9300C13—H130.9300
C3—C41.373 (4)C14—C151.391 (3)
C3—H30.9300C14—C191.397 (3)
C4—C51.385 (3)C15—C161.384 (3)
C4—H40.9300C15—H150.9300
C5—C61.381 (3)C16—C171.379 (3)
C5—H50.9300C16—H160.9300
C6—C71.496 (3)C17—C181.376 (3)
C7—C81.498 (3)C17—H170.9300
C8—C131.387 (3)C18—C191.394 (3)
C8—C91.389 (3)C18—H180.9300
C7—N1—C14121.20 (18)C11—C10—H10119.9
N2—C20—C19177.7 (3)C9—C10—H10119.9
C2—C1—C6120.0 (2)C12—C11—C10120.3 (2)
C2—C1—H1120.0C12—C11—H11119.9
C6—C1—H1120.0C10—C11—H11119.9
C3—C2—C1120.0 (2)C11—C12—C13120.5 (2)
C3—C2—H2120.0C11—C12—H12119.7
C1—C2—H2120.0C13—C12—H12119.7
C4—C3—C2120.8 (2)C8—C13—C12119.6 (2)
C4—C3—H3119.6C8—C13—H13120.2
C2—C3—H3119.6C12—C13—H13120.2
C3—C4—C5119.2 (2)C15—C14—C19118.5 (2)
C3—C4—H4120.4C15—C14—N1123.3 (2)
C5—C4—H4120.4C19—C14—N1118.0 (2)
C6—C5—C4121.1 (2)C16—C15—C14120.0 (2)
C6—C5—H5119.5C16—C15—H15120.0
C4—C5—H5119.5C14—C15—H15120.0
C5—C6—C1118.9 (2)C17—C16—C15121.2 (2)
C5—C6—C7121.21 (19)C17—C16—H16119.4
C1—C6—C7119.8 (2)C15—C16—H16119.4
N1—C7—C6118.03 (18)C18—C17—C16119.7 (2)
N1—C7—C8124.07 (19)C18—C17—H17120.2
C6—C7—C8117.81 (18)C16—C17—H17120.2
C13—C8—C9119.3 (2)C17—C18—C19119.7 (2)
C13—C8—C7120.6 (2)C17—C18—H18120.1
C9—C8—C7120.1 (2)C19—C18—H18120.1
C10—C9—C8120.1 (2)C18—C19—C14120.8 (2)
C10—C9—H9119.9C18—C19—C20119.2 (2)
C8—C9—H9119.9C14—C19—C20120.0 (2)
C11—C10—C9120.1 (3)
C6—C1—C2—C30.3 (4)C8—C9—C10—C111.7 (3)
C1—C2—C3—C40.6 (4)C9—C10—C11—C122.1 (4)
C2—C3—C4—C50.7 (4)C10—C11—C12—C130.3 (4)
C3—C4—C5—C60.5 (4)C9—C8—C13—C122.3 (3)
C4—C5—C6—C10.3 (3)C7—C8—C13—C12178.0 (2)
C4—C5—C6—C7177.0 (2)C11—C12—C13—C82.0 (4)
C2—C1—C6—C50.1 (3)C7—N1—C14—C1559.3 (3)
C2—C1—C6—C7176.9 (2)C7—N1—C14—C19125.6 (2)
C14—N1—C7—C6179.49 (19)C19—C14—C15—C161.8 (3)
C14—N1—C7—C83.9 (3)N1—C14—C15—C16176.8 (2)
C5—C6—C7—N1168.2 (2)C14—C15—C16—C170.1 (4)
C1—C6—C7—N18.6 (3)C15—C16—C17—C180.5 (4)
C5—C6—C7—C88.6 (3)C16—C17—C18—C190.8 (4)
C1—C6—C7—C8174.6 (2)C17—C18—C19—C142.6 (3)
N1—C7—C8—C13118.0 (2)C17—C18—C19—C20177.8 (2)
C6—C7—C8—C1365.4 (3)C15—C14—C19—C183.0 (3)
N1—C7—C8—C962.3 (3)N1—C14—C19—C18178.36 (19)
C6—C7—C8—C9114.3 (2)C15—C14—C19—C20177.3 (2)
C13—C8—C9—C100.5 (3)N1—C14—C19—C202.0 (3)
C7—C8—C9—C10179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg(A)i0.932.893.801 (2)165
C15—H15···Cg(B)ii0.932.773.552 (2)142
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z.
 

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