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1,5-Diphenylpenta-2,4-dien-1-one (DDO) chalcone single crystals, synthesized by a base-catalysed aldol condensation reaction between cinnamaldehyde and acetophenone, have been grown by the slow evaporation of an ethanol solution. The crystals belong to the orthorhombic system with centrosymmetric space group Pbca. The DDO crystals are transparent in the visible region and have a lower optical cut-off at ∼445 nm with a band-gap energy of 2.87 eV. Thermogravimetry/differential scanning calorimetry thermal analysis shows that the crystal is stable up to 375 K and it has a good chemical stability. The vibrational patterns of the chalcone have been investigated by Fourier transform IR and Fourier transform Raman spectroscopy. Microhardness studies were also carried out to elucidate the mechanical behaviour. Theoretical calculations were performed using the Hartree–Fock method with 6-31G(d,p) as the basis set, and the first-order hyperpolarizability is 7.077 × 10−30 electrostatic units, which is >25 times that of urea. The crystalline perfection evaluated by high-resolution X-ray diffraction analysis reveals multiple peaks. The molecular packing leads to a centrosymmetric arrangement, resulting in zero second harmonic generation [χ(2) = 0] efficiency. Interestingly, the bromo- and chloro-substituted chalcones are good nonlinear optical materials.
Supporting information
CCDC reference: 856740
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altornare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Crystal data top
C17H14O | Dx = 1.197 Mg m−3 |
Mr = 234.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2996 reflections |
a = 15.4307 (9) Å | θ = 2.5–23.1° |
b = 10.2659 (5) Å | µ = 0.07 mm−1 |
c = 16.4124 (9) Å | T = 293 K |
V = 2599.9 (2) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
F(000) = 992 | |
Data collection top
Bruker axs kappa apex2 CCD Diffractometer | 2041 independent reflections |
Radiation source: fine-focus sealed tube | 1430 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω and φ scan | θmax = 24.1°, θmin = 2.5° |
Absorption correction: multi-scan SADABS (Bruker, 1999) | h = −13→17 |
Tmin = 0.961, Tmax = 0.992 | k = −11→11 |
11155 measured reflections | l = −18→18 |
Refinement top
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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.4186P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2041 reflections | Δρmax = 0.31 e Å−3 |
164 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (8) |
Crystal data top
C17H14O | V = 2599.9 (2) Å3 |
Mr = 234.28 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 15.4307 (9) Å | µ = 0.07 mm−1 |
b = 10.2659 (5) Å | T = 293 K |
c = 16.4124 (9) Å | 0.30 × 0.20 × 0.20 mm |
Data collection top
Bruker axs kappa apex2 CCD Diffractometer | 2041 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 1999) | 1430 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.992 | Rint = 0.025 |
11155 measured reflections | θmax = 24.1° |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.31 e Å−3 |
2041 reflections | Δρmin = −0.12 e Å−3 |
164 parameters | |
Special details top
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.65266 (13) | 0.14890 (19) | 0.61284 (12) | 0.0630 (5) | |
H1 | 0.6542 | 0.0589 | 0.6193 | 0.076* | |
C2 | 0.69425 (14) | 0.2049 (2) | 0.54790 (13) | 0.0757 (6) | |
H2 | 0.7238 | 0.1529 | 0.5108 | 0.091* | |
C3 | 0.69250 (14) | 0.3374 (2) | 0.53742 (13) | 0.0772 (7) | |
H3 | 0.7201 | 0.3752 | 0.4929 | 0.093* | |
C4 | 0.64976 (14) | 0.4139 (2) | 0.59307 (13) | 0.0722 (6) | |
H4 | 0.6493 | 0.5039 | 0.5866 | 0.087* | |
C5 | 0.60759 (12) | 0.35819 (17) | 0.65836 (11) | 0.0581 (5) | |
H5 | 0.5784 | 0.4108 | 0.6955 | 0.070* | |
C6 | 0.60837 (11) | 0.22454 (16) | 0.66904 (10) | 0.0488 (5) | |
C7 | 0.56664 (12) | 0.15942 (16) | 0.74004 (11) | 0.0548 (5) | |
C8 | 0.52131 (12) | 0.23788 (17) | 0.80105 (11) | 0.0580 (5) | |
H8 | 0.5039 | 0.3217 | 0.7871 | 0.070* | |
C9 | 0.50403 (12) | 0.19458 (18) | 0.87556 (11) | 0.0572 (5) | |
H9 | 0.5218 | 0.1104 | 0.8882 | 0.069* | |
C10 | 0.46067 (12) | 0.26582 (17) | 0.93781 (11) | 0.0583 (5) | |
H10 | 0.4440 | 0.3508 | 0.9260 | 0.070* | |
C11 | 0.44226 (12) | 0.21989 (18) | 1.01173 (11) | 0.0592 (5) | |
H11 | 0.4608 | 0.1356 | 1.0228 | 0.071* | |
C12 | 0.39641 (11) | 0.28646 (18) | 1.07716 (10) | 0.0542 (5) | |
C13 | 0.38653 (13) | 0.42074 (19) | 1.07965 (11) | 0.0633 (6) | |
H13 | 0.4122 | 0.4717 | 1.0395 | 0.076* | |
C14 | 0.33945 (15) | 0.4797 (2) | 1.14036 (13) | 0.0748 (6) | |
H14 | 0.3331 | 0.5698 | 1.1407 | 0.090* | |
C15 | 0.30184 (15) | 0.4064 (2) | 1.20029 (13) | 0.0801 (7) | |
H15 | 0.2693 | 0.4462 | 1.2409 | 0.096* | |
C16 | 0.31232 (15) | 0.2744 (2) | 1.20010 (13) | 0.0802 (7) | |
H16 | 0.2873 | 0.2245 | 1.2411 | 0.096* | |
C17 | 0.35956 (14) | 0.2149 (2) | 1.13985 (11) | 0.0687 (6) | |
H17 | 0.3670 | 0.1251 | 1.1411 | 0.082* | |
O1 | 0.57175 (11) | 0.04065 (12) | 0.74720 (8) | 0.0832 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0654 (14) | 0.0573 (11) | 0.0663 (12) | 0.0012 (10) | 0.0040 (10) | −0.0042 (9) |
C2 | 0.0732 (15) | 0.0849 (15) | 0.0689 (13) | 0.0057 (12) | 0.0193 (12) | −0.0076 (11) |
C3 | 0.0649 (15) | 0.0946 (17) | 0.0720 (14) | −0.0033 (13) | 0.0172 (11) | 0.0164 (12) |
C4 | 0.0711 (15) | 0.0625 (12) | 0.0830 (14) | −0.0038 (11) | 0.0126 (12) | 0.0156 (11) |
C5 | 0.0599 (13) | 0.0535 (11) | 0.0608 (11) | 0.0000 (9) | 0.0062 (10) | 0.0003 (8) |
C6 | 0.0462 (11) | 0.0502 (10) | 0.0500 (10) | −0.0015 (8) | −0.0035 (8) | −0.0006 (8) |
C7 | 0.0582 (12) | 0.0478 (10) | 0.0584 (11) | −0.0011 (9) | −0.0024 (9) | 0.0025 (8) |
C8 | 0.0630 (13) | 0.0505 (10) | 0.0605 (12) | 0.0026 (9) | 0.0051 (10) | 0.0045 (9) |
C9 | 0.0596 (13) | 0.0544 (10) | 0.0575 (11) | 0.0029 (9) | 0.0014 (10) | 0.0038 (9) |
C10 | 0.0601 (12) | 0.0545 (10) | 0.0601 (11) | 0.0021 (9) | 0.0012 (10) | 0.0032 (9) |
C11 | 0.0580 (13) | 0.0641 (11) | 0.0554 (11) | 0.0060 (9) | −0.0024 (10) | 0.0031 (9) |
C12 | 0.0479 (11) | 0.0645 (11) | 0.0502 (10) | −0.0009 (9) | −0.0073 (9) | 0.0008 (9) |
C13 | 0.0614 (13) | 0.0689 (13) | 0.0595 (12) | −0.0100 (10) | 0.0010 (10) | −0.0046 (9) |
C14 | 0.0771 (16) | 0.0704 (13) | 0.0770 (14) | −0.0064 (11) | 0.0002 (12) | −0.0184 (11) |
C15 | 0.0726 (16) | 0.0987 (17) | 0.0689 (14) | −0.0072 (13) | 0.0082 (12) | −0.0234 (12) |
C16 | 0.0808 (17) | 0.0996 (18) | 0.0601 (13) | −0.0126 (14) | 0.0123 (12) | 0.0007 (12) |
C17 | 0.0769 (15) | 0.0701 (12) | 0.0592 (12) | 0.0017 (11) | 0.0032 (11) | 0.0063 (10) |
O1 | 0.1140 (13) | 0.0524 (8) | 0.0832 (10) | 0.0011 (8) | 0.0189 (9) | 0.0061 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.371 (3) | C9—H9 | 0.9300 |
C1—C6 | 1.386 (2) | C10—C11 | 1.332 (2) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.371 (3) | C11—C12 | 1.456 (2) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.373 (3) | C12—C17 | 1.386 (3) |
C3—H3 | 0.9300 | C12—C13 | 1.388 (3) |
C4—C5 | 1.378 (3) | C13—C14 | 1.374 (3) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.383 (2) | C14—C15 | 1.368 (3) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—C7 | 1.490 (2) | C15—C16 | 1.364 (3) |
C7—O1 | 1.2275 (19) | C15—H15 | 0.9300 |
C7—C8 | 1.463 (2) | C16—C17 | 1.372 (3) |
C8—C9 | 1.328 (2) | C16—H16 | 0.9300 |
C8—H8 | 0.9300 | C17—H17 | 0.9300 |
C9—C10 | 1.423 (2) | | |
| | | |
C2—C1—C6 | 120.88 (18) | C10—C9—H9 | 117.2 |
C2—C1—H1 | 119.6 | C11—C10—C9 | 124.89 (17) |
C6—C1—H1 | 119.6 | C11—C10—H10 | 117.6 |
C1—C2—C3 | 120.3 (2) | C9—C10—H10 | 117.6 |
C1—C2—H2 | 119.8 | C10—C11—C12 | 127.52 (18) |
C3—C2—H2 | 119.8 | C10—C11—H11 | 116.2 |
C2—C3—C4 | 119.54 (19) | C12—C11—H11 | 116.2 |
C2—C3—H3 | 120.2 | C17—C12—C13 | 117.35 (18) |
C4—C3—H3 | 120.2 | C17—C12—C11 | 119.88 (18) |
C3—C4—C5 | 120.48 (19) | C13—C12—C11 | 122.77 (17) |
C3—C4—H4 | 119.8 | C14—C13—C12 | 121.16 (19) |
C5—C4—H4 | 119.8 | C14—C13—H13 | 119.4 |
C4—C5—C6 | 120.39 (18) | C12—C13—H13 | 119.4 |
C4—C5—H5 | 119.8 | C15—C14—C13 | 120.2 (2) |
C6—C5—H5 | 119.8 | C15—C14—H14 | 119.9 |
C5—C6—C1 | 118.40 (17) | C13—C14—H14 | 119.9 |
C5—C6—C7 | 122.72 (16) | C16—C15—C14 | 119.6 (2) |
C1—C6—C7 | 118.83 (16) | C16—C15—H15 | 120.2 |
O1—C7—C8 | 120.80 (16) | C14—C15—H15 | 120.2 |
O1—C7—C6 | 119.53 (16) | C15—C16—C17 | 120.5 (2) |
C8—C7—C6 | 119.66 (14) | C15—C16—H16 | 119.8 |
C9—C8—C7 | 122.81 (16) | C17—C16—H16 | 119.8 |
C9—C8—H8 | 118.6 | C16—C17—C12 | 121.1 (2) |
C7—C8—H8 | 118.6 | C16—C17—H17 | 119.4 |
C8—C9—C10 | 125.68 (17) | C12—C17—H17 | 119.4 |
C8—C9—H9 | 117.2 | | |
| | | |
C6—C1—C2—C3 | −0.1 (3) | C7—C8—C9—C10 | 179.67 (17) |
C1—C2—C3—C4 | 0.9 (4) | C8—C9—C10—C11 | 178.5 (2) |
C2—C3—C4—C5 | −1.1 (3) | C9—C10—C11—C12 | −178.39 (18) |
C3—C4—C5—C6 | 0.5 (3) | C10—C11—C12—C17 | 160.3 (2) |
C4—C5—C6—C1 | 0.2 (3) | C10—C11—C12—C13 | −18.9 (3) |
C4—C5—C6—C7 | 177.74 (17) | C17—C12—C13—C14 | −2.2 (3) |
C2—C1—C6—C5 | −0.4 (3) | C11—C12—C13—C14 | 176.97 (18) |
C2—C1—C6—C7 | −178.03 (18) | C12—C13—C14—C15 | 0.6 (3) |
C5—C6—C7—O1 | −177.93 (18) | C13—C14—C15—C16 | 0.9 (3) |
C1—C6—C7—O1 | −0.4 (3) | C14—C15—C16—C17 | −0.6 (4) |
C5—C6—C7—C8 | 1.1 (3) | C15—C16—C17—C12 | −1.1 (3) |
C1—C6—C7—C8 | 178.58 (16) | C13—C12—C17—C16 | 2.5 (3) |
O1—C7—C8—C9 | 18.4 (3) | C11—C12—C17—C16 | −176.72 (18) |
C6—C7—C8—C9 | −160.63 (18) | | |
Experimental details
Crystal data |
Chemical formula | C17H14O |
Mr | 234.28 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 15.4307 (9), 10.2659 (5), 16.4124 (9) |
V (Å3) | 2599.9 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker axs kappa apex2 CCD Diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 1999) |
Tmin, Tmax | 0.961, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11155, 2041, 1430 |
Rint | 0.025 |
θmax (°) | 24.1 |
(sin θ/λ)max (Å−1) | 0.574 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.130, 1.07 |
No. of reflections | 2041 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.12 |
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