organic compounds
4-{2-[4-(Dimethylamino)phenyl]ethylidene}benzonitrile
aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, Universidade de São Paulo, USP, São Carlos, SP, Brazil
*Correspondence e-mail: rodimo26@yahoo.es
In the crystal of the title compound, C17H16N2, molecules are linked by C—H⋯N hydrogen bonds, forming rings of graph-set motifs R21(6) and R22(10). The title molecule is close to planar, with a dihedral angle between the aromatic rings of 0.6 (1)°. Torsion angles confirm a conformational trans structure.
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
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 2000); cell 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).
Supporting information
10.1107/S1600536809018674/bv2116sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018674/bv2116Isup2.hkl
By means of Wittig reaction (Maryanoff & Reitz, 1989), the 4-dimethylamino-benzyl-triphenylphosphonium iodide was prepared. The title stilbene was obtained by the reaction of equimolar quantities of phosphonium salt and 4-cyano benzaldehyde (0.02 mol) in THF solution. The mixture was maintained with stirring under argon atmosphere. The reaction mixture was kept at 273 K and it was dropped with a solution of tert-butanol and potassium tert-butoxide. Crystals of suitable quality for single-crystal X-ray diffraction were grown in chloroform. Thin layer
(TLC) was used to confirm the structure of the individual compounds. IR spectra were recorded on a Shimadzu FT—IR 8400 spectrophotometer.N-(p-chlorophenyl)maleimide. Yellow crystals; yield 40%; mp 384 (1) K. IR (KBr) 3051 cm-1 (C—H), 2922 cm-1 (=C—H), 2217 cm-1 (C—N), 1590 cm-1 (C=C).
The
P 21/n was uniquely assigned from the All H-atoms were located from difference maps and then they were treated as riding atoms [Caro—H= 0.93 A° and Csp3—H= 0.96 A°, Uiso(H)= 1.2Ueq(Caro), Uiso(H)= 1.5Ueq(Csp3)).Some reflections were omitted in the FCF file perhaps because the crystal was placed in a position very close to the detector and therefore some diffracted reflections at low angle were potentially covered by the beamstop.
Data collection: COLLECT (Nonius, 2000); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).C17H16N2 | F(000) = 528 |
Mr = 248.32 | Dx = 1.196 Mg m−3 |
Monoclinic, P21/n | Melting point: 384(1) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2009 (2) Å | Cell parameters from 4640 reflections |
b = 7.9706 (3) Å | θ = 2.9–27.5° |
c = 27.9619 (11) Å | µ = 0.07 mm−1 |
β = 93.6027 (13)° | T = 291 K |
V = 1379.28 (9) Å3 | Prism, yellow |
Z = 4 | 0.28 × 0.14 × 0.08 mm |
Bruker–Nonius KappaCCD diffractometer | 1428 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Horizonally mounted graphite crystal monochromator | θmax = 25.1°, θmin = 3.3° |
Detector resolution: 9 pixels mm-1 | h = −7→7 |
CCD scans | k = −9→9 |
4640 measured reflections | l = −33→33 |
2443 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0926P)2 + 0.0631P] where P = (Fo2 + 2Fc2)/3 |
2443 reflections | (Δ/σ)max < 0.001 |
192 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C17H16N2 | V = 1379.28 (9) Å3 |
Mr = 248.32 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.2009 (2) Å | µ = 0.07 mm−1 |
b = 7.9706 (3) Å | T = 291 K |
c = 27.9619 (11) Å | 0.28 × 0.14 × 0.08 mm |
β = 93.6027 (13)° |
Bruker–Nonius KappaCCD diffractometer | 1428 reflections with I > 2σ(I) |
4640 measured reflections | Rint = 0.037 |
2443 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.12 e Å−3 |
2443 reflections | Δρmin = −0.16 e Å−3 |
192 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 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 | Occ. (<1) | |
N1 | 0.0557 (2) | 0.34596 (18) | 0.41210 (5) | 0.0821 (5) | |
N2 | 1.1813 (3) | 0.3178 (3) | 0.01870 (7) | 0.1246 (8) | |
C1 | −0.1199 (3) | 0.4594 (3) | 0.41729 (7) | 0.1036 (7) | |
H1A | −0.2208 | 0.4503 | 0.3899 | 0.155* | |
H1B | −0.0658 | 0.5721 | 0.4197 | 0.155* | |
H1C | −0.1912 | 0.4320 | 0.4458 | 0.155* | |
C2 | 0.1629 (4) | 0.2885 (3) | 0.45672 (7) | 0.1152 (8) | |
H2A | 0.2872 | 0.3573 | 0.4645 | 0.173* | |
H2B | 0.2075 | 0.1740 | 0.4533 | 0.173* | |
H2C | 0.0648 | 0.2961 | 0.4819 | 0.173* | |
C3 | 0.1650 (3) | 0.34508 (19) | 0.37074 (6) | 0.0701 (5) | |
C4 | 0.0836 (3) | 0.4231 (2) | 0.32872 (6) | 0.0797 (5) | |
H4 | −0.0494 | 0.4772 | 0.3282 | 0.096* | |
C5 | 0.1975 (4) | 0.4211 (2) | 0.28796 (7) | 0.0934 (6) | |
H5 | 0.1395 | 0.4750 | 0.2606 | 0.112* | |
C6 | 0.3973 (4) | 0.3406 (3) | 0.28637 (9) | 0.1056 (8) | |
C7 | 0.4692 (4) | 0.2609 (3) | 0.32802 (11) | 0.1121 (8) | |
H7 | 0.5992 | 0.2026 | 0.3283 | 0.135* | |
C8 | 0.3615 (3) | 0.2627 (3) | 0.36853 (8) | 0.0935 (6) | |
H8 | 0.4204 | 0.2074 | 0.3956 | 0.112* | |
C9A | 0.5574 (9) | 0.3187 (5) | 0.25116 (12) | 0.0751 (9) | 0.60 |
H9A | 0.6791 | 0.2535 | 0.2588 | 0.075* | 0.60 |
C10A | 0.5323 (10) | 0.3906 (6) | 0.20808 (14) | 0.0727 (9) | 0.60 |
H10A | 0.4141 | 0.4596 | 0.2005 | 0.073* | 0.60 |
C11 | 0.6991 (4) | 0.3586 (3) | 0.17129 (8) | 0.0981 (7) | |
C12 | 0.6354 (3) | 0.4322 (3) | 0.12852 (8) | 0.0905 (6) | |
H12 | 0.5050 | 0.4902 | 0.1261 | 0.109* | |
C13 | 0.7552 (3) | 0.4241 (2) | 0.08934 (6) | 0.0803 (5) | |
H13 | 0.7071 | 0.4769 | 0.0610 | 0.096* | |
C14 | 0.9488 (3) | 0.3369 (2) | 0.09185 (6) | 0.0732 (5) | |
C15 | 1.0198 (3) | 0.2606 (2) | 0.13431 (7) | 0.0889 (6) | |
H15 | 1.1502 | 0.2025 | 0.1365 | 0.107* | |
C16 | 0.8952 (5) | 0.2714 (3) | 0.17349 (7) | 0.1034 (7) | |
H16 | 0.9429 | 0.2194 | 0.2020 | 0.124* | |
C17 | 1.0761 (3) | 0.3277 (3) | 0.05086 (7) | 0.0880 (6) | |
C9B | 0.4576 (10) | 0.3811 (9) | 0.2327 (3) | 0.0708 (13) | 0.40 |
H9B | 0.3677 | 0.4425 | 0.2113 | 0.071* | 0.40 |
C10B | 0.6456 (9) | 0.3229 (8) | 0.2215 (3) | 0.0737 (13) | 0.40 |
H10B | 0.7370 | 0.2629 | 0.2429 | 0.074* | 0.40 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0877 (10) | 0.0838 (10) | 0.0747 (10) | 0.0108 (8) | 0.0039 (8) | 0.0070 (7) |
N2 | 0.1098 (15) | 0.150 (2) | 0.1173 (16) | 0.0013 (13) | 0.0338 (13) | −0.0152 (13) |
C1 | 0.0975 (14) | 0.1195 (17) | 0.0957 (14) | 0.0204 (13) | 0.0203 (11) | 0.0006 (12) |
C2 | 0.1341 (19) | 0.1260 (18) | 0.0844 (14) | 0.0219 (15) | −0.0015 (13) | 0.0214 (12) |
C3 | 0.0744 (11) | 0.0586 (10) | 0.0770 (11) | −0.0002 (8) | 0.0043 (9) | −0.0007 (8) |
C4 | 0.0851 (12) | 0.0759 (12) | 0.0776 (12) | 0.0027 (10) | 0.0001 (9) | −0.0036 (9) |
C5 | 0.1241 (17) | 0.0847 (13) | 0.0718 (12) | −0.0215 (13) | 0.0105 (11) | −0.0066 (10) |
C6 | 0.1192 (19) | 0.0875 (15) | 0.1158 (18) | −0.0355 (14) | 0.0531 (16) | −0.0418 (13) |
C7 | 0.1003 (17) | 0.0895 (16) | 0.150 (2) | 0.0056 (13) | 0.0389 (17) | −0.0172 (16) |
C8 | 0.0871 (13) | 0.0776 (13) | 0.1165 (16) | 0.0126 (11) | 0.0113 (12) | 0.0065 (11) |
C9A | 0.077 (2) | 0.071 (2) | 0.076 (2) | 0.0044 (19) | −0.003 (2) | −0.0016 (19) |
C10A | 0.072 (3) | 0.068 (2) | 0.077 (3) | 0.001 (2) | 0.000 (2) | −0.002 (2) |
C11 | 0.1216 (18) | 0.0869 (15) | 0.0880 (15) | −0.0386 (14) | 0.0244 (14) | −0.0234 (12) |
C12 | 0.0883 (13) | 0.0880 (14) | 0.0967 (15) | −0.0082 (10) | 0.0177 (11) | −0.0184 (11) |
C13 | 0.0801 (12) | 0.0784 (12) | 0.0821 (12) | −0.0027 (9) | 0.0024 (10) | 0.0007 (9) |
C14 | 0.0737 (11) | 0.0689 (11) | 0.0769 (12) | −0.0083 (9) | 0.0034 (9) | −0.0078 (9) |
C15 | 0.0949 (14) | 0.0773 (12) | 0.0920 (14) | 0.0007 (11) | −0.0143 (11) | −0.0034 (10) |
C16 | 0.153 (2) | 0.0870 (14) | 0.0688 (13) | −0.0326 (15) | −0.0075 (13) | 0.0035 (10) |
C17 | 0.0785 (12) | 0.0918 (14) | 0.0936 (14) | −0.0045 (11) | 0.0064 (11) | −0.0123 (11) |
C9B | 0.072 (4) | 0.066 (3) | 0.072 (4) | −0.003 (3) | −0.010 (3) | 0.002 (3) |
C10B | 0.078 (3) | 0.072 (3) | 0.070 (4) | 0.002 (3) | −0.005 (3) | 0.005 (3) |
N1—C3 | 1.377 (2) | C9A—C10A | 1.334 (6) |
N1—C1 | 1.430 (2) | C9A—H9A | 0.9300 |
N1—C2 | 1.451 (2) | C9A—H10B | 1.2345 |
N2—C17 | 1.146 (2) | C10A—C11 | 1.525 (6) |
C1—H1A | 0.9600 | C10A—H10A | 0.9300 |
C1—H1B | 0.9600 | C10A—H9B | 1.1103 |
C1—H1C | 0.9600 | C11—C12 | 1.368 (3) |
C2—H2A | 0.9600 | C11—C16 | 1.399 (3) |
C2—H2B | 0.9600 | C11—C10B | 1.491 (8) |
C2—H2C | 0.9600 | C12—C13 | 1.363 (2) |
C3—C8 | 1.389 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.396 (2) | C13—C14 | 1.385 (2) |
C4—C5 | 1.378 (3) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—C15 | 1.381 (2) |
C5—C6 | 1.398 (3) | C14—C17 | 1.434 (3) |
C5—H5 | 0.9300 | C15—C16 | 1.382 (3) |
C6—C7 | 1.376 (3) | C15—H15 | 0.9300 |
C6—C9A | 1.452 (5) | C16—H16 | 0.9300 |
C6—C9B | 1.603 (9) | C9B—C10B | 1.310 (9) |
C7—C8 | 1.350 (3) | C9B—H9B | 0.9300 |
C7—H7 | 0.9300 | C10B—H10B | 0.9300 |
C8—H8 | 0.9300 | ||
C3—N1—C1 | 120.45 (15) | C10A—C9A—H9A | 119.5 |
C3—N1—C2 | 119.86 (16) | C6—C9A—H9A | 119.5 |
C1—N1—C2 | 115.03 (16) | C10A—C9A—H10B | 92.3 |
N1—C1—H1A | 109.5 | C6—C9A—H10B | 146.5 |
N1—C1—H1B | 109.5 | C9A—C10A—C11 | 119.5 (6) |
H1A—C1—H1B | 109.5 | C9A—C10A—H10A | 120.3 |
N1—C1—H1C | 109.5 | C11—C10A—H10A | 120.3 |
H1A—C1—H1C | 109.5 | C9A—C10A—H9B | 98.2 |
H1B—C1—H1C | 109.5 | C11—C10A—H9B | 141.5 |
N1—C2—H2A | 109.5 | C12—C11—C16 | 117.02 (19) |
N1—C2—H2B | 109.5 | C12—C11—C10B | 146.8 (4) |
H2A—C2—H2B | 109.5 | C16—C11—C10B | 96.2 (3) |
N1—C2—H2C | 109.5 | C12—C11—C10A | 110.3 (3) |
H2A—C2—H2C | 109.5 | C16—C11—C10A | 132.7 (3) |
H2B—C2—H2C | 109.5 | C13—C12—C11 | 122.7 (2) |
N1—C3—C8 | 121.29 (17) | C13—C12—H12 | 118.7 |
N1—C3—C4 | 122.25 (16) | C11—C12—H12 | 118.7 |
C8—C3—C4 | 116.45 (17) | C12—C13—C14 | 119.85 (18) |
C5—C4—C3 | 120.92 (18) | C12—C13—H13 | 120.1 |
C5—C4—H4 | 119.5 | C14—C13—H13 | 120.1 |
C3—C4—H4 | 119.5 | C15—C14—C13 | 119.55 (17) |
C4—C5—C6 | 122.2 (2) | C15—C14—C17 | 120.16 (18) |
C4—C5—H5 | 118.9 | C13—C14—C17 | 120.28 (17) |
C6—C5—H5 | 118.9 | C14—C15—C16 | 119.3 (2) |
C7—C6—C5 | 115.18 (19) | C14—C15—H15 | 120.3 |
C7—C6—C9A | 108.6 (3) | C16—C15—H15 | 120.3 |
C5—C6—C9A | 136.2 (3) | C15—C16—C11 | 121.58 (19) |
C7—C6—C9B | 143.5 (3) | C15—C16—H16 | 119.2 |
C5—C6—C9B | 101.4 (3) | C11—C16—H16 | 119.2 |
C8—C7—C6 | 123.7 (2) | N2—C17—C14 | 178.3 (2) |
C8—C7—H7 | 118.2 | C10B—C9B—C6 | 114.5 (9) |
C6—C7—H7 | 118.2 | C10B—C9B—H9B | 122.7 |
C7—C8—C3 | 121.6 (2) | C6—C9B—H9B | 122.8 |
C7—C8—H8 | 119.2 | C9B—C10B—C11 | 114.2 (9) |
C3—C8—H8 | 119.2 | C9B—C10B—H10B | 123.0 |
C10A—C9A—C6 | 121.0 (7) | C11—C10B—H10B | 122.8 |
C1—N1—C3—C8 | 166.46 (18) | C9A—C10A—C11—C16 | −4.6 (5) |
C2—N1—C3—C8 | 11.9 (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—C5 | 179.55 (15) | C10A—C11—C12—C13 | 179.7 (2) |
C8—C3—C4—C5 | −1.8 (3) | C11—C12—C13—C14 | 0.7 (3) |
C3—C4—C5—C6 | 0.5 (3) | C12—C13—C14—C15 | −0.7 (3) |
C4—C5—C6—C7 | 1.3 (3) | C12—C13—C14—C17 | −179.97 (16) |
C4—C5—C6—C9A | −178.0 (2) | C13—C14—C15—C16 | 0.6 (3) |
C4—C5—C6—C9B | −178.5 (2) | C17—C14—C15—C16 | 179.78 (16) |
C5—C6—C7—C8 | −2.1 (3) | C14—C15—C16—C11 | −0.3 (3) |
C9A—C6—C7—C8 | 177.5 (2) | C12—C11—C16—C15 | 0.3 (3) |
C9B—C6—C7—C8 | 177.6 (4) | C10B—C11—C16—C15 | 179.1 (2) |
C6—C7—C8—C3 | 0.9 (3) | C10A—C11—C16—C15 | −179.9 (2) |
N1—C3—C8—C7 | 179.79 (17) | C7—C6—C9B—C10B | −1.6 (7) |
C4—C3—C8—C7 | 1.1 (3) | C5—C6—C9B—C10B | 178.1 (4) |
C7—C6—C9A—C10A | −176.8 (3) | C9A—C6—C9B—C10B | −1.3 (3) |
C5—C6—C9A—C10A | 2.5 (5) | C6—C9B—C10B—C11 | 179.1 (3) |
C9B—C6—C9A—C10A | 3.3 (4) | C12—C11—C10B—C9B | 1.2 (7) |
C6—C9A—C10A—C11 | −177.4 (3) | C16—C11—C10B—C9B | −176.8 (4) |
C9A—C10A—C11—C12 | 175.2 (3) | C10A—C11—C10B—C9B | 4.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···N2i | 0.96 | 2.99 | 3.858 (3) | 151 |
C2—H2C···N2i | 0.96 | 2.80 | 3.646 (3) | 147 |
C13—H13···N2ii | 0.93 | 2.88 | 3.696 (3) | 147 |
Symmetry codes: (i) x−3/2, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2 |
Mr | 248.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 6.2009 (2), 7.9706 (3), 27.9619 (11) |
β (°) | 93.6027 (13) |
V (Å3) | 1379.28 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.28 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Bruker–Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4640, 2443, 1428 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.173, 1.02 |
No. of reflections | 2443 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.16 |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PARST95 (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···N2i | 0.96 | 2.99 | 3.858 (3) | 150.7 |
C2—H2C···N2i | 0.96 | 2.80 | 3.646 (3) | 147.2 |
C13—H13···N2ii | 0.93 | 2.88 | 3.696 (3) | 146.7 |
Symmetry codes: (i) x−3/2, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z. |
Acknowledgements
RM-F is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge license to the Cambridge Structural Database (Allen, 2002). RM-F also acknowledges Dr K. A. Abboud of the University of Florida, USA, for his valuable discussions on this structure and the Universidad del Valle, Colombia, for partial financial support.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blanchard-Desce, M., Ledoux, I., Lehn, J. M., Malthete, J. & Zyss, J. (1988). J. Chem. Soc. Chem. Commun. pp. 737–739. CrossRef Web of Science Google Scholar
Craig, N. C., Groner, P. & McKean, D. C. (2006). J. Phys. Chem. A, 110, 7461–7469. Web of Science CrossRef PubMed CAS Google Scholar
Daum, R., Hansson, T., Norenberg, R., Schwarzer, D. & Schroeder, J. (1995). Chem. Phys. Lett. 246, 607–614. CrossRef CAS Web of Science Google Scholar
Etter, M. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kubicki, A. A. (2007). Chem. Phys. Lett. 439, 243–246. Web of Science CrossRef CAS Google Scholar
Lapouyade, R., Kuhn, A., Letard, J. F. & Retting, W. (1993). Chem. Phys. Lett. 208, 48–58. CrossRef CAS Web of Science Google Scholar
Maryanoff, B. E. & Reitz, A. B. (1989). J. Chem. Rev. 89, 863. CrossRef Web of Science Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Papper, V., Pines, D., Likhtenshtein, G. & Pines, E. (1997). J. Photochem. Photobiol. A, 111, 87–96. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Polyene systems are often used as π conjugating units as they provide an effective pathway for the efficient push-pull charge transfer between the donor and acceptor groups (Blanchard-Desce et al., 1988). Stilbene materials are expected to have diverse applications in photochemistry, fluorescense and non linear optical (NLO) processes when donor-acceptor substituents are introduced in the phenyl rings in order to spread the conjugation over the whole molecule (Lapouyade et al., 1993; Papper et al., 1997). Spectroscopic properties of the title 4-dimethylamino-4-cyano-stilbene (DCS) system have been extensively studied (Daum et al., 1995; Kubicki, 2007). Nevertheless, a survey of the literature shows that crystallographic information of stilbene compounds is still rather scarce.
The main aim of this work is to present the molecular and crystal structure of the DCS, one of the best exponents of the stilbene series, to analyse its configuration, its C=C double bond and to show the supramolecular arranging of the system. A perspective view of the molecule of the title compound, showing the atomic numbering scheme, is given in Fig. 1. The DCS molecule suffers a rotational disorder, atoms C9 and C10 were modeled as exchanged with a minor occupancy fraction refined to 39 (1)%. The dimethylamino group forms a dihedral angle of 20.9 (2)° with respect to its phenyl ring. The phenyl rings of the title structure is almost coplanar showing a dihedral angle of 0.6 (1)° between the planes of the rings. The phenyl rings are twisted out of the ethylene bond plane, and are defined by the torsion angles C16—C11=C10A—C9A and C10A=C9A—C6—C5 (Table 1). The C9A=C10A bond length is close to the reported value for the ethylene C=C bond length [1.330 (1) A°] (Craig et al., 2006). The title molecule shows a torsion angle C6 C9A C10A C11 equal to 177.4 (3)° and it also shows that the bond angles between the olefinic double bond and the two aromatic rings C6—C9A=C10A and C11—C10A=C9A are close to 120° (Table 1) indicating small repulsion between the aromatic rings. These values allow to define its configuration as trans.
The molecules of the title compound are linked into sheets by a C—H···N weak intermolecular interactions (Table 2) (Nardelli, 1995) generating two dimensional substructures. In the first substructure, methyl amino C1 and C2 atoms in the molecule at (1 + x, y, z) acts as a hydrogen bond donors to cyano N2 atom in the molecule at (-1/2 + x, 1/2 - y, 1/2 + z) so forming a R21(6) rings (Etter, 1990) and generating sheets which lie in the (104) plane (Fig. 2, Supp. Mat). In the second substructure, atom C13 in the molecule at (x, y, z) acts as a hydrogen bond donor to cyano N2 atom in the molecule at (3/2 - x, -1/2 + y, 1/2 - z) so forming a R22(10) rings which are running parallel to the [112] direction (Fig. 3, Supp. Mat).