organic compounds
4-[(E)-3-(4-Methylphenyl)-3-oxoprop-1-en-1-yl]benzonitrile
aDepartment of Chemistry, Sri Dharmasthala Manjunatheshwara Institute of Technology, Ujire -574 240, and affiliated to, Visvesvaraya Technological University, Belagavi, Karnataka, India, bLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: y.ramli@um5s.net.ma
In the title molecule C17H13NO, the phenyl rings are inclined to one another by 48.04 (9)°. In the crystal, weak C—H⋯π(ring) interactions form a layered structure parallel to the ab plane.
Keywords: crystal structure; olefin; benzonitrile; carbonyl; chalcone.
CCDC reference: 2009913
Structure description
). Apart from their biological applications, some with appropriate substituents are also reported to be good NLO materials (Shettigar et al., 2006). As part of our work in this area, we now describe the synthesis and structure of the title compound (Fig. 1).
are compounds that can be easily synthesized, and their analogs can also be isolated from natural products (Dhar, 1981The 4-cyanophenyl and 4-methylbenzoyl units are disposed in a trans fashion about the C7=C8 double bond. The dihedral angle between the planes of the C1–C6 and C10–C15 benzene rings is 48.04 (9)° and these benzene rings are inclined to the plane defined by the propene atoms C7, C8 and C9 by 16.0 (1) and 32.6 (1)°, respectively, while O1 lies 0.24 (1) Å away from the propene plane.
In the crystal, stacked molecules form layers parallel to the ab plane with the para substituents on the phenyl rings on the outside surfaces of the layers (Figs. 2 and 3). The molecules constituting each layer are associated through very weak C2—H2⋯Cg2, C5—H5⋯Cg2, C12—H12⋯Cg1 and C15—H15⋯Cg1 interactions across centers of symmetry (Table 1; Cg1 and Cg2 are the centroids of rings C1–C6 and C10–C15, respectively).
Synthesis and crystallization
An equimolar mixture of 4-methylacetophenone (0.01 mol) and 4-cyanobenzaldehyde (0.01 mol) in ethanol (30 ml) was stirred for 3 h in the presence of NaOH (5 ml, 30%) at 283 K. The crude solid obtained was collected by filtration and dried. It was purified by repeated recrystallization. Thin layer
was used to check the purity of the compound. Single crystals were grown from ethanol solution by slow evaporation, yield 86%, m.p. 415 K.Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 2009913
https://doi.org/10.1107/S2414314620008007/vm4044sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620008007/vm4044Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620008007/vm4044Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H13NO | Z = 2 |
Mr = 247.28 | F(000) = 260 |
Triclinic, P1 | Dx = 1.250 Mg m−3 |
a = 5.8686 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.4955 (3) Å | Cell parameters from 3797 reflections |
c = 15.2792 (5) Å | θ = 3.0–72.3° |
α = 102.195 (2)° | µ = 0.61 mm−1 |
β = 90.649 (2)° | T = 296 K |
γ = 90.454 (2)° | Block, colourless |
V = 656.86 (4) Å3 | 0.28 × 0.27 × 0.22 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2432 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 2010 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
ω scans | θmax = 72.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −6→7 |
Tmin = 0.85, Tmax = 0.88 | k = −8→9 |
4923 measured reflections | l = −17→18 |
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)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.1069P)2 + 0.0967P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2432 reflections | Δρmax = 0.21 e Å−3 |
174 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL 2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.045 (6) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.2283 (2) | 0.7780 (2) | 0.53901 (10) | 0.0780 (5) | |
N1 | 0.7607 (4) | 0.3451 (3) | 0.04455 (13) | 0.0857 (6) | |
C1 | 0.2420 (3) | 0.6151 (2) | 0.32693 (12) | 0.0518 (4) | |
C2 | 0.1652 (3) | 0.6113 (3) | 0.23990 (13) | 0.0580 (5) | |
H2 | 0.022952 | 0.658976 | 0.231111 | 0.070* | |
C3 | 0.2945 (3) | 0.5390 (3) | 0.16681 (12) | 0.0613 (5) | |
H3 | 0.240243 | 0.537500 | 0.109219 | 0.074* | |
C4 | 0.5071 (3) | 0.4682 (2) | 0.17993 (12) | 0.0551 (5) | |
C5 | 0.5873 (3) | 0.4695 (2) | 0.26642 (12) | 0.0556 (5) | |
H5 | 0.729197 | 0.421032 | 0.274983 | 0.067* | |
C6 | 0.4562 (3) | 0.5427 (3) | 0.33882 (12) | 0.0558 (5) | |
H6 | 0.510499 | 0.544070 | 0.396389 | 0.067* | |
C7 | 0.0932 (3) | 0.6890 (2) | 0.40188 (13) | 0.0565 (5) | |
H7 | −0.057548 | 0.708491 | 0.387342 | 0.068* | |
C8 | 0.1490 (3) | 0.7312 (3) | 0.48794 (13) | 0.0606 (5) | |
H8 | 0.299879 | 0.721005 | 0.505402 | 0.073* | |
C9 | −0.0252 (3) | 0.7946 (3) | 0.55739 (13) | 0.0580 (5) | |
C10 | 0.0541 (3) | 0.8750 (2) | 0.64974 (12) | 0.0519 (4) | |
C11 | 0.2692 (3) | 0.9570 (3) | 0.66834 (13) | 0.0576 (5) | |
H11 | 0.369553 | 0.959948 | 0.621986 | 0.069* | |
C12 | 0.3322 (3) | 1.0337 (3) | 0.75564 (14) | 0.0611 (5) | |
H12 | 0.474772 | 1.089423 | 0.766886 | 0.073* | |
C13 | 0.1902 (3) | 1.0302 (2) | 0.82681 (13) | 0.0587 (5) | |
C14 | −0.0233 (3) | 0.9458 (3) | 0.80743 (13) | 0.0613 (5) | |
H14 | −0.121386 | 0.939348 | 0.854076 | 0.074* | |
C15 | −0.0909 (3) | 0.8723 (3) | 0.72091 (13) | 0.0574 (5) | |
H15 | −0.235381 | 0.819966 | 0.709725 | 0.069* | |
C16 | 0.2597 (4) | 1.1135 (3) | 0.92168 (15) | 0.0803 (7) | |
H16A | 0.405925 | 1.172112 | 0.922209 | 0.120* | |
H16B | 0.268634 | 1.019697 | 0.955689 | 0.120* | |
H16C | 0.149003 | 1.201979 | 0.947754 | 0.120* | |
C17 | 0.6484 (4) | 0.3977 (3) | 0.10434 (13) | 0.0648 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0489 (7) | 0.1059 (12) | 0.0725 (9) | −0.0032 (7) | −0.0061 (6) | 0.0041 (8) |
N1 | 0.0888 (14) | 0.1008 (15) | 0.0662 (12) | 0.0074 (11) | 0.0107 (10) | 0.0141 (10) |
C1 | 0.0492 (9) | 0.0493 (9) | 0.0571 (9) | −0.0090 (7) | −0.0044 (7) | 0.0121 (7) |
C2 | 0.0506 (9) | 0.0646 (11) | 0.0614 (10) | −0.0032 (8) | −0.0078 (8) | 0.0195 (8) |
C3 | 0.0596 (10) | 0.0720 (12) | 0.0545 (10) | −0.0105 (9) | −0.0090 (8) | 0.0190 (8) |
C4 | 0.0560 (10) | 0.0534 (9) | 0.0558 (10) | −0.0086 (7) | −0.0011 (7) | 0.0115 (7) |
C5 | 0.0489 (9) | 0.0591 (10) | 0.0593 (10) | −0.0033 (7) | −0.0044 (7) | 0.0139 (8) |
C6 | 0.0543 (9) | 0.0619 (10) | 0.0515 (9) | −0.0046 (8) | −0.0084 (7) | 0.0132 (7) |
C7 | 0.0499 (9) | 0.0556 (10) | 0.0637 (11) | −0.0027 (7) | −0.0052 (8) | 0.0120 (8) |
C8 | 0.0503 (9) | 0.0696 (12) | 0.0606 (10) | 0.0019 (8) | −0.0028 (8) | 0.0109 (9) |
C9 | 0.0476 (9) | 0.0609 (10) | 0.0642 (11) | 0.0008 (7) | −0.0032 (8) | 0.0105 (8) |
C10 | 0.0443 (8) | 0.0508 (9) | 0.0604 (10) | 0.0019 (7) | 0.0004 (7) | 0.0109 (7) |
C11 | 0.0450 (9) | 0.0593 (10) | 0.0672 (11) | −0.0029 (7) | 0.0050 (7) | 0.0105 (8) |
C12 | 0.0457 (8) | 0.0578 (10) | 0.0758 (12) | −0.0042 (7) | −0.0042 (8) | 0.0055 (9) |
C13 | 0.0576 (10) | 0.0524 (10) | 0.0643 (11) | 0.0019 (8) | −0.0046 (8) | 0.0082 (8) |
C14 | 0.0568 (10) | 0.0627 (11) | 0.0633 (11) | −0.0039 (8) | 0.0073 (8) | 0.0106 (8) |
C15 | 0.0437 (8) | 0.0583 (10) | 0.0685 (11) | −0.0044 (7) | 0.0026 (7) | 0.0099 (8) |
C16 | 0.0880 (15) | 0.0769 (14) | 0.0691 (13) | −0.0031 (12) | −0.0106 (11) | 0.0008 (11) |
C17 | 0.0694 (12) | 0.0678 (12) | 0.0572 (11) | −0.0050 (9) | −0.0026 (9) | 0.0135 (9) |
O1—C9 | 1.220 (2) | C8—H8 | 0.9300 |
N1—C17 | 1.136 (3) | C9—C10 | 1.481 (3) |
C1—C2 | 1.394 (3) | C10—C15 | 1.392 (3) |
C1—C6 | 1.398 (3) | C10—C11 | 1.399 (2) |
C1—C7 | 1.464 (3) | C11—C12 | 1.381 (3) |
C2—C3 | 1.373 (3) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.382 (3) |
C3—C4 | 1.389 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.399 (3) |
C4—C5 | 1.396 (3) | C13—C16 | 1.503 (3) |
C4—C17 | 1.439 (3) | C14—C15 | 1.373 (3) |
C5—C6 | 1.373 (3) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—H16A | 0.9600 |
C7—C8 | 1.323 (3) | C16—H16B | 0.9600 |
C7—H7 | 0.9300 | C16—H16C | 0.9600 |
C8—C9 | 1.489 (3) | ||
C2—C1—C6 | 118.38 (16) | C10—C9—C8 | 118.29 (15) |
C2—C1—C7 | 118.95 (16) | C15—C10—C11 | 118.40 (17) |
C6—C1—C7 | 122.64 (16) | C15—C10—C9 | 119.20 (16) |
C3—C2—C1 | 121.61 (17) | C11—C10—C9 | 122.39 (16) |
C3—C2—H2 | 119.2 | C12—C11—C10 | 119.91 (17) |
C1—C2—H2 | 119.2 | C12—C11—H11 | 120.0 |
C2—C3—C4 | 119.20 (17) | C10—C11—H11 | 120.0 |
C2—C3—H3 | 120.4 | C11—C12—C13 | 122.10 (17) |
C4—C3—H3 | 120.4 | C11—C12—H12 | 119.0 |
C3—C4—C5 | 120.28 (17) | C13—C12—H12 | 119.0 |
C3—C4—C17 | 120.01 (17) | C12—C13—C14 | 117.43 (17) |
C5—C4—C17 | 119.69 (17) | C12—C13—C16 | 121.89 (18) |
C6—C5—C4 | 119.81 (16) | C14—C13—C16 | 120.68 (18) |
C6—C5—H5 | 120.1 | C15—C14—C13 | 121.31 (17) |
C4—C5—H5 | 120.1 | C15—C14—H14 | 119.3 |
C5—C6—C1 | 120.71 (16) | C13—C14—H14 | 119.3 |
C5—C6—H6 | 119.6 | C14—C15—C10 | 120.83 (16) |
C1—C6—H6 | 119.6 | C14—C15—H15 | 119.6 |
C8—C7—C1 | 127.33 (17) | C10—C15—H15 | 119.6 |
C8—C7—H7 | 116.3 | C13—C16—H16A | 109.5 |
C1—C7—H7 | 116.3 | C13—C16—H16B | 109.5 |
C7—C8—C9 | 121.20 (17) | H16A—C16—H16B | 109.5 |
C7—C8—H8 | 119.4 | C13—C16—H16C | 109.5 |
C9—C8—H8 | 119.4 | H16A—C16—H16C | 109.5 |
O1—C9—C10 | 120.84 (17) | H16B—C16—H16C | 109.5 |
O1—C9—C8 | 120.86 (17) | N1—C17—C4 | 178.8 (2) |
C6—C1—C2—C3 | 0.0 (3) | O1—C9—C10—C15 | 22.7 (3) |
C7—C1—C2—C3 | −178.17 (16) | C8—C9—C10—C15 | −156.09 (18) |
C1—C2—C3—C4 | −0.1 (3) | O1—C9—C10—C11 | −156.2 (2) |
C2—C3—C4—C5 | 0.4 (3) | C8—C9—C10—C11 | 25.0 (3) |
C2—C3—C4—C17 | −177.81 (17) | C15—C10—C11—C12 | −0.4 (3) |
C3—C4—C5—C6 | −0.6 (3) | C9—C10—C11—C12 | 178.50 (16) |
C17—C4—C5—C6 | 177.68 (16) | C10—C11—C12—C13 | 1.0 (3) |
C4—C5—C6—C1 | 0.4 (3) | C11—C12—C13—C14 | −0.2 (3) |
C2—C1—C6—C5 | −0.1 (3) | C11—C12—C13—C16 | 179.91 (18) |
C7—C1—C6—C5 | 177.96 (16) | C12—C13—C14—C15 | −1.2 (3) |
C2—C1—C7—C8 | −167.96 (18) | C16—C13—C14—C15 | 178.69 (19) |
C6—C1—C7—C8 | 14.0 (3) | C13—C14—C15—C10 | 1.8 (3) |
C1—C7—C8—C9 | −176.11 (17) | C11—C10—C15—C14 | −1.0 (3) |
C7—C8—C9—O1 | 13.5 (3) | C9—C10—C15—C14 | −179.91 (16) |
C7—C8—C9—C10 | −167.68 (18) |
Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg2i | 0.93 | 2.98 | 3.645 (2) | 129 |
C5—H5···Cg2ii | 0.93 | 2.91 | 3.5929 (18) | 132 |
C12—H12···Cg1iii | 0.93 | 2.98 | 3.637 (2) | 129 |
C15—H15···Cg1iv | 0.93 | 2.99 | 3.604 (2) | 125 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+1, −z+1. |
Acknowledgements
DA is grateful to the Directorate of Minorities, Government of Karnataka, for providing a research fellowship and Visvesvaraya Technological University, Belagavi, for access to research facilities.
Funding information
The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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