Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033491/pr2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033491/pr2008Isup2.hkl |
CCDC reference: 657798
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.143
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.114 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound is synthesized according to the method reported in the literature (Furniss et al., 1989) with a yield of 75–80%. The compound was purified by recrystallization from ethanol. The crystal grew by slow evaporation from an acetone:toluene solution (50:50). Analysis for C18H16O2: Found (Calculated): C: 81.50 (81.79); H: 6.01(6.10).
H atoms were placed at calculated positions and refined using a riding model on the respective carrier atoms.
The title compound, (I), is a optically active molecule. The present-day demand is for large, high quality ferroelectric and piezoelectric single crystals with minimum defects and inhomogenities. The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crystals, alkali halide crystals, and nonlinear optical (NLO) crystals. The NLO effect in organic molecules originates from a strong donor–acceptor intermolecular interaction, a delocalized π-electron system, and also the ability to crystallize in noncentrosymmetric space groups. Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of non-centrosymmetric crystals (Fichou et al., 1988). The molecular hyperpolarizability is strongly influenced not only by the electronic effect but also by the steric effect of the substituent (Cho et al., 1996). Among several organic compounds reported for NLO properties, chalcone derivatives are notable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show an NLO property with two planar rings connected through a conjugated double bond (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira et al., 2002, Sarojini et al., 2006). The crystal structures of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006), 5-phenyl-1-(2-thienyl)penta-2,4-dien-1-one (Yathirajan et al., 2007), and 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (Harrison et al., 2006) have been reported. This paper reports crystal structure of the title compound. Fig 1 shows the molecular structure. The geometry of the molecule is unexceptional. The dihedral angle between the two phenyl groups is 9.28 (9)\%. The crystal packing is stabilized by van der Waals forces.
For related literature, see: Butcher et al. (2006); Cho et al. (1996); Fichou et al. (1988); Furniss et al. (1989); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Sarojini et al. (2006); Tam et al. (1989); Uchida et al. (1998); Yathirajan et al. (2007).
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).
Fig. 1. The molecular structure of (I). Thermal ellipsoids at the 50% probability level. |
C18H16O2 | F(000) = 560 |
Mr = 264.32 | Dx = 1.229 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23 reflections |
a = 29.017 (7) Å | θ = 7.9–16.8° |
b = 5.8088 (14) Å | µ = 0.08 mm−1 |
c = 8.4868 (10) Å | T = 298 K |
β = 93.308 (16)° | Block, colourless |
V = 1428.1 (5) Å3 | 0.35 × 0.30 × 0.28 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | Rint = 0.114 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 4.5° |
ω scans | h = −35→35 |
13388 measured reflections | k = −6→6 |
2633 independent reflections | l = −10→10 |
1558 reflections with I > 2σ(I) |
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)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0295P)2 + 0.4375P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2633 reflections | Δρmax = 0.11 e Å−3 |
181 parameters | Δρmin = −0.15 e Å−3 |
0 restraints |
C18H16O2 | V = 1428.1 (5) Å3 |
Mr = 264.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 29.017 (7) Å | µ = 0.08 mm−1 |
b = 5.8088 (14) Å | T = 298 K |
c = 8.4868 (10) Å | 0.35 × 0.30 × 0.28 mm |
β = 93.308 (16)° |
Nonius KappaCCD area-detector diffractometer | 1558 reflections with I > 2σ(I) |
13388 measured reflections | Rint = 0.114 |
2633 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.11 e Å−3 |
2633 reflections | Δρmin = −0.15 e Å−3 |
181 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 | ||
C1 | 0.38172 (9) | 0.0845 (4) | −0.2302 (3) | 0.0578 (6) | |
C2 | 0.36674 (9) | −0.1304 (4) | −0.2890 (3) | 0.0646 (7) | |
C3 | 0.39574 (11) | −0.2695 (5) | −0.3692 (3) | 0.0749 (8) | |
C4 | 0.43995 (12) | −0.2026 (5) | −0.3913 (3) | 0.0838 (9) | |
C5 | 0.45590 (10) | 0.0061 (5) | −0.3321 (3) | 0.0819 (8) | |
C6 | 0.42687 (10) | 0.1465 (5) | −0.2519 (3) | 0.0712 (7) | |
C7 | 0.35161 (9) | 0.2417 (4) | −0.1507 (3) | 0.0647 (7) | |
C8 | 0.31018 (9) | 0.2028 (4) | −0.0991 (3) | 0.0642 (7) | |
C9 | 0.28328 (9) | 0.3786 (4) | −0.0280 (3) | 0.0674 (7) | |
C10 | 0.24440 (9) | 0.3508 (4) | 0.0427 (3) | 0.0684 (7) | |
C11 | 0.22146 (9) | 0.5437 (4) | 0.1185 (3) | 0.0634 (7) | |
C12 | 0.17642 (8) | 0.5074 (4) | 0.1882 (3) | 0.0570 (6) | |
C13 | 0.15943 (9) | 0.6766 (4) | 0.2867 (3) | 0.0664 (7) | |
C14 | 0.11768 (9) | 0.6524 (4) | 0.3513 (3) | 0.0688 (7) | |
C15 | 0.09115 (9) | 0.4579 (4) | 0.3199 (3) | 0.0631 (7) | |
C16 | 0.10710 (9) | 0.2878 (4) | 0.2227 (3) | 0.0697 (7) | |
C17 | 0.14966 (9) | 0.3132 (4) | 0.1591 (3) | 0.0677 (7) | |
C18 | 0.02246 (11) | 0.2487 (6) | 0.3656 (4) | 0.0971 (10) | |
O1 | 0.23951 (7) | 0.7363 (3) | 0.1259 (3) | 0.0929 (7) | |
O2 | 0.04997 (6) | 0.4496 (3) | 0.3901 (2) | 0.0784 (6) | |
H2 | 0.3369 | −0.1794 | −0.2736 | 0.078* | |
H3 | 0.3852 | −0.4108 | −0.4089 | 0.090* | |
H4 | 0.4592 | −0.2977 | −0.4462 | 0.101* | |
H5 | 0.4860 | 0.0518 | −0.3461 | 0.098* | |
H6 | 0.4379 | 0.2865 | −0.2114 | 0.085* | |
H7 | 0.3630 | 0.3902 | −0.1337 | 0.078* | |
H8 | 0.2979 | 0.0548 | −0.1094 | 0.077* | |
H9 | 0.2945 | 0.5288 | −0.0322 | 0.081* | |
H10 | 0.2311 | 0.2046 | 0.0445 | 0.082* | |
H13 | 0.1768 | 0.8086 | 0.3088 | 0.080* | |
H14 | 0.1071 | 0.7674 | 0.4168 | 0.083* | |
H16 | 0.0894 | 0.1570 | 0.2001 | 0.084* | |
H17 | 0.1605 | 0.1967 | 0.0954 | 0.081* | |
H18A | 0.0156 | 0.2276 | 0.2547 | 0.146* | |
H18B | −0.0057 | 0.2664 | 0.4184 | 0.146* | |
H18C | 0.0389 | 0.1163 | 0.4073 | 0.146* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0763 (17) | 0.0467 (15) | 0.0503 (13) | 0.0012 (13) | 0.0038 (12) | 0.0023 (12) |
C2 | 0.0840 (18) | 0.0550 (16) | 0.0548 (14) | −0.0046 (14) | 0.0018 (13) | 0.0003 (13) |
C3 | 0.111 (2) | 0.0544 (17) | 0.0593 (16) | −0.0032 (17) | 0.0069 (16) | −0.0036 (13) |
C4 | 0.108 (3) | 0.072 (2) | 0.0723 (19) | 0.0150 (18) | 0.0178 (17) | −0.0006 (16) |
C5 | 0.080 (2) | 0.076 (2) | 0.090 (2) | 0.0022 (17) | 0.0174 (16) | 0.0018 (18) |
C6 | 0.083 (2) | 0.0578 (17) | 0.0732 (17) | −0.0076 (15) | 0.0098 (15) | −0.0011 (14) |
C7 | 0.0801 (19) | 0.0522 (15) | 0.0618 (15) | −0.0038 (14) | 0.0041 (14) | −0.0027 (13) |
C8 | 0.0757 (19) | 0.0502 (15) | 0.0662 (16) | −0.0014 (14) | −0.0015 (14) | −0.0042 (12) |
C9 | 0.0787 (19) | 0.0543 (16) | 0.0687 (16) | 0.0011 (14) | −0.0009 (14) | −0.0021 (14) |
C10 | 0.0698 (18) | 0.0538 (16) | 0.0814 (18) | −0.0005 (13) | 0.0013 (15) | −0.0091 (14) |
C11 | 0.0692 (17) | 0.0502 (16) | 0.0696 (16) | 0.0000 (13) | −0.0063 (13) | −0.0030 (13) |
C12 | 0.0656 (16) | 0.0454 (14) | 0.0589 (14) | 0.0050 (12) | −0.0059 (12) | −0.0014 (12) |
C13 | 0.0731 (19) | 0.0469 (15) | 0.0782 (17) | 0.0020 (13) | −0.0045 (15) | −0.0080 (13) |
C14 | 0.0793 (19) | 0.0512 (16) | 0.0753 (17) | 0.0108 (14) | −0.0008 (15) | −0.0112 (13) |
C15 | 0.0666 (17) | 0.0588 (16) | 0.0634 (15) | 0.0092 (14) | −0.0017 (13) | 0.0016 (14) |
C16 | 0.0761 (19) | 0.0540 (16) | 0.0786 (18) | −0.0076 (14) | −0.0002 (15) | −0.0122 (14) |
C17 | 0.0776 (19) | 0.0542 (16) | 0.0711 (17) | 0.0006 (14) | 0.0037 (14) | −0.0126 (13) |
C18 | 0.083 (2) | 0.092 (2) | 0.118 (3) | −0.0125 (19) | 0.0188 (19) | −0.008 (2) |
O1 | 0.0942 (15) | 0.0578 (12) | 0.1283 (18) | −0.0129 (11) | 0.0214 (12) | −0.0151 (12) |
O2 | 0.0736 (12) | 0.0743 (13) | 0.0878 (13) | 0.0044 (10) | 0.0081 (10) | −0.0039 (10) |
C1—C6 | 1.385 (3) | C16—C17 | 1.387 (3) |
C1—C2 | 1.401 (3) | C18—O2 | 1.420 (3) |
C1—C7 | 1.455 (3) | C2—H2 | 0.9300 |
C2—C3 | 1.374 (3) | C3—H3 | 0.9300 |
C3—C4 | 1.367 (4) | C4—H4 | 0.9300 |
C4—C5 | 1.379 (4) | C5—H5 | 0.9300 |
C5—C6 | 1.379 (4) | C6—H6 | 0.9300 |
C7—C8 | 1.325 (3) | C7—H7 | 0.9300 |
C8—C9 | 1.437 (3) | C8—H8 | 0.9300 |
C9—C10 | 1.320 (3) | C9—H9 | 0.9300 |
C10—C11 | 1.467 (3) | C10—H10 | 0.9300 |
C11—O1 | 1.232 (3) | C13—H13 | 0.9300 |
C11—C12 | 1.483 (3) | C14—H14 | 0.9300 |
C12—C17 | 1.382 (3) | C16—H16 | 0.9300 |
C12—C13 | 1.395 (3) | C17—H17 | 0.9300 |
C13—C14 | 1.368 (3) | C18—H18A | 0.9600 |
C14—C15 | 1.383 (3) | C18—H18B | 0.9600 |
C15—O2 | 1.369 (3) | C18—H18C | 0.9600 |
C15—C16 | 1.384 (3) | ||
C6—C1—C2 | 117.5 (2) | C2—C3—H3 | 119.6 |
C6—C1—C7 | 120.0 (2) | C3—C4—H4 | 120.0 |
C2—C1—C7 | 122.7 (2) | C5—C4—H4 | 120.0 |
C3—C2—C1 | 120.6 (3) | C6—C5—H5 | 120.2 |
C4—C3—C2 | 120.7 (3) | C4—C5—H5 | 120.2 |
C3—C4—C5 | 119.9 (3) | C5—C6—H6 | 119.2 |
C6—C5—C4 | 119.5 (3) | C1—C6—H6 | 119.2 |
C5—C6—C1 | 121.7 (3) | C8—C7—H7 | 115.5 |
C8—C7—C1 | 129.1 (2) | C1—C7—H7 | 115.5 |
C7—C8—C9 | 123.1 (2) | C7—C8—H8 | 118.5 |
C10—C9—C8 | 127.3 (2) | C9—C8—H8 | 118.5 |
C9—C10—C11 | 121.9 (2) | C10—C9—H9 | 116.4 |
O1—C11—C10 | 120.5 (2) | C8—C9—H9 | 116.4 |
O1—C11—C12 | 119.5 (2) | C9—C10—H10 | 119.0 |
C10—C11—C12 | 120.1 (2) | C11—C10—H10 | 119.0 |
C17—C12—C13 | 117.8 (2) | C14—C13—H13 | 119.3 |
C17—C12—C11 | 123.1 (2) | C12—C13—H13 | 119.3 |
C13—C12—C11 | 119.3 (2) | C13—C14—H14 | 119.8 |
C14—C13—C12 | 121.4 (2) | C15—C14—H14 | 119.8 |
C13—C14—C15 | 120.3 (2) | C15—C16—H16 | 120.2 |
O2—C15—C16 | 124.5 (2) | C17—C16—H16 | 120.2 |
O2—C15—C14 | 115.9 (2) | C12—C17—H17 | 119.2 |
C16—C15—C14 | 119.5 (2) | C16—C17—H17 | 119.2 |
C15—C16—C17 | 119.6 (2) | O2—C18—H18A | 109.5 |
C12—C17—C16 | 121.6 (2) | O2—C18—H18B | 109.5 |
C15—O2—C18 | 117.7 (2) | H18A—C18—H18B | 109.5 |
C3—C2—H2 | 119.7 | O2—C18—H18C | 109.5 |
C1—C2—H2 | 119.7 | H18A—C18—H18C | 109.5 |
C4—C3—H3 | 119.6 | H18B—C18—H18C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C18H16O2 |
Mr | 264.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 29.017 (7), 5.8088 (14), 8.4868 (10) |
β (°) | 93.308 (16) |
V (Å3) | 1428.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13388, 2633, 1558 |
Rint | 0.114 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.143, 1.12 |
No. of reflections | 2633 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.15 |
Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).
The title compound, (I), is a optically active molecule. The present-day demand is for large, high quality ferroelectric and piezoelectric single crystals with minimum defects and inhomogenities. The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crystals, alkali halide crystals, and nonlinear optical (NLO) crystals. The NLO effect in organic molecules originates from a strong donor–acceptor intermolecular interaction, a delocalized π-electron system, and also the ability to crystallize in noncentrosymmetric space groups. Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of non-centrosymmetric crystals (Fichou et al., 1988). The molecular hyperpolarizability is strongly influenced not only by the electronic effect but also by the steric effect of the substituent (Cho et al., 1996). Among several organic compounds reported for NLO properties, chalcone derivatives are notable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show an NLO property with two planar rings connected through a conjugated double bond (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira et al., 2002, Sarojini et al., 2006). The crystal structures of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006), 5-phenyl-1-(2-thienyl)penta-2,4-dien-1-one (Yathirajan et al., 2007), and 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (Harrison et al., 2006) have been reported. This paper reports crystal structure of the title compound. Fig 1 shows the molecular structure. The geometry of the molecule is unexceptional. The dihedral angle between the two phenyl groups is 9.28 (9)\%. The crystal packing is stabilized by van der Waals forces.