Literature DB >> 21583220

4-{2-[4-(Dimethyl-amino)phen-yl]ethyl-idene}benzonitrile.

Rodolfo Moreno-Fuquen, Richard Dvries, Jahyr Theodoro, Javier Ellena.   

Abstract

In the crystal of the title compound, C(17)H(16)N(2), mol-ecules are linked by C-H⋯N hydrogen bonds, forming rings of graph-set motifs R(2) (1)(6) and R(2) (2)(10). The title mol-ecule is close to planar, with a dihedral angle between the aromatic rings of 0.6 (1)°. Torsion angles confirm a conformational trans structure.

Entities:  

Year:  2009        PMID： 21583220      PMCID： PMC2969814          DOI： 10.1107/S1600536809018674

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background information on photonic materials, see: Blanchard-Desce et al. (1988 ▶); Lapouyade et al. (1993 ▶); Papper et al. (1997 ▶). For background information on spectroscopic properties, see: Daum et al. (1995 ▶); Kubicki (2007 ▶). For graph-set motifs, see: Etter (1990 ▶). For related literature, see: Craig et al. (2006 ▶); Maryanoff & Reitz (1989 ▶).

Experimental

Crystal data

C17H16N2 M = 248.32 Monoclinic, a = 6.2009 (2) Å b = 7.9706 (3) Å c = 27.9619 (11) Å β = 93.6027 (13)° V = 1379.28 (9) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 291 K 0.28 × 0.14 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer Absorption correction: none 4640 measured reflections 2443 independent reflections 1428 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.173 S = 1.02 2443 reflections 192 parameters H-atom parameters constrained Δρmax = 0.12 e Å−3 Δρmin = −0.16 e Å−3 Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PARST95 (Nardelli, 1995 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018674/bv2116sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018674/bv2116Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H16N2F(000) = 528
Mr = 248.32Dx = 1.196 Mg m−3
Monoclinic, P21/nMelting point: 384(1) K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 6.2009 (2) ÅCell parameters from 4640 reflections
b = 7.9706 (3) Åθ = 2.9–27.5°
c = 27.9619 (11) ŵ = 0.07 mm−1
β = 93.6027 (13)°T = 291 K
V = 1379.28 (9) Å3Prism, yellow
Z = 40.28 × 0.14 × 0.08 mm
Bruker–Nonius KappaCCD diffractometer1428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
horizonally mounted graphite crystalθmax = 25.1°, θmin = 3.3°
Detector resolution: 9 pixels mm-1h = −7→7
CCD scansk = −9→9
4640 measured reflectionsl = −33→33
2443 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0926P)2 + 0.0631P] where P = (Fo2 + 2Fc2)/3
2443 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.12 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
N10.0557 (2)0.34596 (18)0.41210 (5)0.0821 (5)
N21.1813 (3)0.3178 (3)0.01870 (7)0.1246 (8)
C1−0.1199 (3)0.4594 (3)0.41729 (7)0.1036 (7)
H1A−0.22080.45030.38990.155*
H1B−0.06580.57210.41970.155*
H1C−0.19120.43200.44580.155*
C20.1629 (4)0.2885 (3)0.45672 (7)0.1152 (8)
H2A0.28720.35730.46450.173*
H2B0.20750.17400.45330.173*
H2C0.06480.29610.48190.173*
C30.1650 (3)0.34508 (19)0.37074 (6)0.0701 (5)
C40.0836 (3)0.4231 (2)0.32872 (6)0.0797 (5)
H4−0.04940.47720.32820.096*
C50.1975 (4)0.4211 (2)0.28796 (7)0.0934 (6)
H50.13950.47500.26060.112*
C60.3973 (4)0.3406 (3)0.28637 (9)0.1056 (8)
C70.4692 (4)0.2609 (3)0.32802 (11)0.1121 (8)
H70.59920.20260.32830.135*
C80.3615 (3)0.2627 (3)0.36853 (8)0.0935 (6)
H80.42040.20740.39560.112*
C9A0.5574 (9)0.3187 (5)0.25116 (12)0.0751 (9)0.60
H9A0.67910.25350.25880.075*0.60
C10A0.5323 (10)0.3906 (6)0.20808 (14)0.0727 (9)0.60
H10A0.41410.45960.20050.073*0.60
C110.6991 (4)0.3586 (3)0.17129 (8)0.0981 (7)
C120.6354 (3)0.4322 (3)0.12852 (8)0.0905 (6)
H120.50500.49020.12610.109*
C130.7552 (3)0.4241 (2)0.08934 (6)0.0803 (5)
H130.70710.47690.06100.096*
C140.9488 (3)0.3369 (2)0.09185 (6)0.0732 (5)
C151.0198 (3)0.2606 (2)0.13431 (7)0.0889 (6)
H151.15020.20250.13650.107*
C160.8952 (5)0.2714 (3)0.17349 (7)0.1034 (7)
H160.94290.21940.20200.124*
C171.0761 (3)0.3277 (3)0.05086 (7)0.0880 (6)
C9B0.4576 (10)0.3811 (9)0.2327 (3)0.0708 (13)0.40
H9B0.36770.44250.21130.071*0.40
C10B0.6456 (9)0.3229 (8)0.2215 (3)0.0737 (13)0.40
H10B0.73700.26290.24290.074*0.40
U11U22U33U12U13U23
N10.0877 (10)0.0838 (10)0.0747 (10)0.0108 (8)0.0039 (8)0.0070 (7)
N20.1098 (15)0.150 (2)0.1173 (16)0.0013 (13)0.0338 (13)−0.0152 (13)
C10.0975 (14)0.1195 (17)0.0957 (14)0.0204 (13)0.0203 (11)0.0006 (12)
C20.1341 (19)0.1260 (18)0.0844 (14)0.0219 (15)−0.0015 (13)0.0214 (12)
C30.0744 (11)0.0586 (10)0.0770 (11)−0.0002 (8)0.0043 (9)−0.0007 (8)
C40.0851 (12)0.0759 (12)0.0776 (12)0.0027 (10)0.0001 (9)−0.0036 (9)
C50.1241 (17)0.0847 (13)0.0718 (12)−0.0215 (13)0.0105 (11)−0.0066 (10)
C60.1192 (19)0.0875 (15)0.1158 (18)−0.0355 (14)0.0531 (16)−0.0418 (13)
C70.1003 (17)0.0895 (16)0.150 (2)0.0056 (13)0.0389 (17)−0.0172 (16)
C80.0871 (13)0.0776 (13)0.1165 (16)0.0126 (11)0.0113 (12)0.0065 (11)
C9A0.077 (2)0.071 (2)0.076 (2)0.0044 (19)−0.003 (2)−0.0016 (19)
C10A0.072 (3)0.068 (2)0.077 (3)0.001 (2)0.000 (2)−0.002 (2)
C110.1216 (18)0.0869 (15)0.0880 (15)−0.0386 (14)0.0244 (14)−0.0234 (12)
C120.0883 (13)0.0880 (14)0.0967 (15)−0.0082 (10)0.0177 (11)−0.0184 (11)
C130.0801 (12)0.0784 (12)0.0821 (12)−0.0027 (9)0.0024 (10)0.0007 (9)
C140.0737 (11)0.0689 (11)0.0769 (12)−0.0083 (9)0.0034 (9)−0.0078 (9)
C150.0949 (14)0.0773 (12)0.0920 (14)0.0007 (11)−0.0143 (11)−0.0034 (10)
C160.153 (2)0.0870 (14)0.0688 (13)−0.0326 (15)−0.0075 (13)0.0035 (10)
C170.0785 (12)0.0918 (14)0.0936 (14)−0.0045 (11)0.0064 (11)−0.0123 (11)
C9B0.072 (4)0.066 (3)0.072 (4)−0.003 (3)−0.010 (3)0.002 (3)
C10B0.078 (3)0.072 (3)0.070 (4)0.002 (3)−0.005 (3)0.005 (3)
N1—C31.377 (2)C9A—C10A1.334 (6)
N1—C11.430 (2)C9A—H9A0.9300
N1—C21.451 (2)C9A—H10B1.2345
N2—C171.146 (2)C10A—C111.525 (6)
C1—H1A0.9600C10A—H10A0.9300
C1—H1B0.9600C10A—H9B1.1103
C1—H1C0.9600C11—C121.368 (3)
C2—H2A0.9600C11—C161.399 (3)
C2—H2B0.9600C11—C10B1.491 (8)
C2—H2C0.9600C12—C131.363 (2)
C3—C81.389 (3)C12—H120.9300
C3—C41.396 (2)C13—C141.385 (2)
C4—C51.378 (3)C13—H130.9300
C4—H40.9300C14—C151.381 (2)
C5—C61.398 (3)C14—C171.434 (3)
C5—H50.9300C15—C161.382 (3)
C6—C71.376 (3)C15—H150.9300
C6—C9A1.452 (5)C16—H160.9300
C6—C9B1.603 (9)C9B—C10B1.310 (9)
C7—C81.350 (3)C9B—H9B0.9300
C7—H70.9300C10B—H10B0.9300
C8—H80.9300
C3—N1—C1120.45 (15)C10A—C9A—H9A119.5
C3—N1—C2119.86 (16)C6—C9A—H9A119.5
C1—N1—C2115.03 (16)C10A—C9A—H10B92.3
N1—C1—H1A109.5C6—C9A—H10B146.5
N1—C1—H1B109.5C9A—C10A—C11119.5 (6)
H1A—C1—H1B109.5C9A—C10A—H10A120.3
N1—C1—H1C109.5C11—C10A—H10A120.3
H1A—C1—H1C109.5C9A—C10A—H9B98.2
H1B—C1—H1C109.5C11—C10A—H9B141.5
N1—C2—H2A109.5C12—C11—C16117.02 (19)
N1—C2—H2B109.5C12—C11—C10B146.8 (4)
H2A—C2—H2B109.5C16—C11—C10B96.2 (3)
N1—C2—H2C109.5C12—C11—C10A110.3 (3)
H2A—C2—H2C109.5C16—C11—C10A132.7 (3)
H2B—C2—H2C109.5C13—C12—C11122.7 (2)
N1—C3—C8121.29 (17)C13—C12—H12118.7
N1—C3—C4122.25 (16)C11—C12—H12118.7
C8—C3—C4116.45 (17)C12—C13—C14119.85 (18)
C5—C4—C3120.92 (18)C12—C13—H13120.1
C5—C4—H4119.5C14—C13—H13120.1
C3—C4—H4119.5C15—C14—C13119.55 (17)
C4—C5—C6122.2 (2)C15—C14—C17120.16 (18)
C4—C5—H5118.9C13—C14—C17120.28 (17)
C6—C5—H5118.9C14—C15—C16119.3 (2)
C7—C6—C5115.18 (19)C14—C15—H15120.3
C7—C6—C9A108.6 (3)C16—C15—H15120.3
C5—C6—C9A136.2 (3)C15—C16—C11121.58 (19)
C7—C6—C9B143.5 (3)C15—C16—H16119.2
C5—C6—C9B101.4 (3)C11—C16—H16119.2
C8—C7—C6123.7 (2)N2—C17—C14178.3 (2)
C8—C7—H7118.2C10B—C9B—C6114.5 (9)
C6—C7—H7118.2C10B—C9B—H9B122.7
C7—C8—C3121.6 (2)C6—C9B—H9B122.8
C7—C8—H8119.2C9B—C10B—C11114.2 (9)
C3—C8—H8119.2C9B—C10B—H10B123.0
C10A—C9A—C6121.0 (7)C11—C10B—H10B122.8
C1—N1—C3—C8166.46 (18)C9A—C10A—C11—C16−4.6 (5)
C2—N1—C3—C811.9 (3)C9A—C10A—C11—C10B−2.9 (4)
C1—N1—C3—C4−14.9 (3)C16—C11—C12—C13−0.5 (3)
C2—N1—C3—C4−169.52 (18)C10B—C11—C12—C13−178.3 (4)
N1—C3—C4—C5179.55 (15)C10A—C11—C12—C13179.7 (2)
C8—C3—C4—C5−1.8 (3)C11—C12—C13—C140.7 (3)
C3—C4—C5—C60.5 (3)C12—C13—C14—C15−0.7 (3)
C4—C5—C6—C71.3 (3)C12—C13—C14—C17−179.97 (16)
C4—C5—C6—C9A−178.0 (2)C13—C14—C15—C160.6 (3)
C4—C5—C6—C9B−178.5 (2)C17—C14—C15—C16179.78 (16)
C5—C6—C7—C8−2.1 (3)C14—C15—C16—C11−0.3 (3)
C9A—C6—C7—C8177.5 (2)C12—C11—C16—C150.3 (3)
C9B—C6—C7—C8177.6 (4)C10B—C11—C16—C15179.1 (2)
C6—C7—C8—C30.9 (3)C10A—C11—C16—C15−179.9 (2)
N1—C3—C8—C7179.79 (17)C7—C6—C9B—C10B−1.6 (7)
C4—C3—C8—C71.1 (3)C5—C6—C9B—C10B178.1 (4)
C7—C6—C9A—C10A−176.8 (3)C9A—C6—C9B—C10B−1.3 (3)
C5—C6—C9A—C10A2.5 (5)C6—C9B—C10B—C11179.1 (3)
C9B—C6—C9A—C10A3.3 (4)C12—C11—C10B—C9B1.2 (7)
C6—C9A—C10A—C11−177.4 (3)C16—C11—C10B—C9B−176.8 (4)
C9A—C10A—C11—C12175.2 (3)C10A—C11—C10B—C9B4.4 (4)
D—H···AD—HH···AD···AD—H···A
C1—H1C···N2i0.962.993.858 (3)151
C2—H2C···N2i0.962.803.646 (3)147
C13—H13···N2ii0.932.883.696 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1—H1C⋯N2i0.962.993.858 (3)151
C2—H2C⋯N2i0.962.803.646 (3)147
C13—H13⋯N2ii0.932.883.696 (3)147

Symmetry codes: (i) ; (ii) .

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