Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021328/ci6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021328/ci6085Isup2.hkl |
CCDC reference: 180558
NaOH (0.22 g) in alcohol solution (100 ml) was treated with 0.5 M 4-hydroxyacetophenone (6.8 g) and stirred well. 0.5 M of benzaldehyde (5.3 g) was added to the solution. Stirring was continued for 2 h. A viscous liquid was obtained when stirring was no longer effective. It was kept in a refrigerator overnight. A yellow crude product was obtained; yield (5.9 g). Compound (I) was recrystallized from the rectified spirit.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C15H12O2 | Dx = 1.287 Mg m−3 |
Mr = 224.25 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, Pbca | Cell parameters from 25 reflections |
a = 8.4663 (10) Å | θ = 20–30° |
b = 22.384 (2) Å | µ = 0.68 mm−1 |
c = 12.216 (3) Å | T = 293 K |
V = 2315.2 (6) Å3 | Rectangular, yellow |
Z = 8 | 0.30 × 0.22 × 0.15 mm |
F(000) = 944 |
Enraf-Nonius CAD-4 diffractometer | 1518 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 67.9°, θmin = 4.0° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→26 |
Tmin = 0.822, Tmax = 0.905 | l = −14→0 |
2107 measured reflections | 2 standard reflections every 120 min |
2107 independent reflections | intensity decay: none |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0493P)2 + 0.8408P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2107 reflections | Δρmax = 0.15 e Å−3 |
156 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (3) |
C15H12O2 | V = 2315.2 (6) Å3 |
Mr = 224.25 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 8.4663 (10) Å | µ = 0.68 mm−1 |
b = 22.384 (2) Å | T = 293 K |
c = 12.216 (3) Å | 0.30 × 0.22 × 0.15 mm |
Enraf-Nonius CAD-4 diffractometer | 1518 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.822, Tmax = 0.905 | 2 standard reflections every 120 min |
2107 measured reflections | intensity decay: none |
2107 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.15 e Å−3 |
2107 reflections | Δρmin = −0.14 e Å−3 |
156 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 | ||
O1 | −0.0431 (2) | 0.12610 (7) | 0.61789 (12) | 0.0610 (5) | |
O2 | 0.3845 (2) | 0.35874 (7) | 0.59586 (12) | 0.0666 (5) | |
H2A | 0.4137 | 0.3589 | 0.5319 | 0.100* | |
C10 | 0.1188 (2) | 0.20795 (9) | 0.66607 (15) | 0.0428 (5) | |
C6 | −0.1178 (2) | 0.07359 (9) | 0.95098 (16) | 0.0467 (5) | |
C9 | 0.0247 (2) | 0.15458 (9) | 0.69126 (16) | 0.0468 (5) | |
C11 | 0.1465 (3) | 0.25249 (10) | 0.74367 (16) | 0.0507 (5) | |
H11 | 0.1050 | 0.2482 | 0.8137 | 0.061* | |
C13 | 0.2987 (2) | 0.30913 (9) | 0.61535 (16) | 0.0485 (5) | |
C15 | 0.1843 (2) | 0.21562 (9) | 0.56201 (16) | 0.0466 (5) | |
H15 | 0.1666 | 0.1869 | 0.5085 | 0.056* | |
C14 | 0.2745 (2) | 0.26497 (9) | 0.53727 (15) | 0.0486 (5) | |
H14 | 0.3193 | 0.2688 | 0.4681 | 0.058* | |
C12 | 0.2333 (3) | 0.30244 (10) | 0.71920 (16) | 0.0566 (6) | |
H12 | 0.2486 | 0.3318 | 0.7720 | 0.068* | |
C7 | −0.0908 (2) | 0.09406 (9) | 0.83833 (16) | 0.0478 (5) | |
H7 | −0.1518 | 0.0763 | 0.7840 | 0.057* | |
C8 | 0.0116 (3) | 0.13520 (10) | 0.80625 (16) | 0.0512 (5) | |
H8 | 0.0777 | 0.1525 | 0.8581 | 0.061* | |
C1 | −0.2448 (3) | 0.03666 (11) | 0.9737 (2) | 0.0666 (7) | |
H1 | −0.3089 | 0.0236 | 0.9167 | 0.080* | |
C5 | −0.0229 (3) | 0.09103 (11) | 1.03738 (18) | 0.0611 (6) | |
H5 | 0.0644 | 0.1152 | 1.0241 | 0.073* | |
C4 | −0.0561 (3) | 0.07298 (11) | 1.14339 (19) | 0.0694 (7) | |
H4 | 0.0082 | 0.0854 | 1.2008 | 0.083* | |
C2 | −0.2777 (4) | 0.01894 (13) | 1.0799 (2) | 0.0818 (9) | |
H2 | −0.3645 | −0.0053 | 1.0941 | 0.098* | |
C3 | −0.1823 (4) | 0.03712 (11) | 1.1638 (2) | 0.0738 (8) | |
H3 | −0.2039 | 0.0249 | 1.2350 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0782 (11) | 0.0629 (9) | 0.0420 (8) | −0.0100 (9) | −0.0059 (8) | 0.0045 (7) |
O2 | 0.0833 (12) | 0.0696 (10) | 0.0469 (8) | −0.0219 (9) | 0.0072 (8) | 0.0022 (8) |
C10 | 0.0417 (10) | 0.0509 (11) | 0.0358 (9) | 0.0072 (9) | −0.0010 (8) | 0.0054 (8) |
C6 | 0.0532 (12) | 0.0430 (10) | 0.0439 (11) | 0.0028 (10) | 0.0072 (10) | 0.0015 (9) |
C9 | 0.0465 (11) | 0.0535 (12) | 0.0405 (10) | 0.0065 (10) | −0.0008 (9) | 0.0058 (9) |
C11 | 0.0571 (12) | 0.0612 (12) | 0.0337 (9) | 0.0035 (11) | 0.0059 (9) | 0.0042 (9) |
C13 | 0.0503 (12) | 0.0538 (12) | 0.0414 (10) | −0.0014 (10) | −0.0005 (9) | 0.0060 (9) |
C15 | 0.0499 (11) | 0.0546 (12) | 0.0352 (10) | 0.0047 (10) | −0.0008 (9) | 0.0015 (9) |
C14 | 0.0522 (12) | 0.0621 (13) | 0.0316 (9) | 0.0015 (10) | 0.0021 (9) | 0.0049 (9) |
C12 | 0.0698 (15) | 0.0611 (13) | 0.0390 (11) | −0.0037 (12) | 0.0038 (11) | −0.0028 (9) |
C7 | 0.0515 (12) | 0.0503 (11) | 0.0414 (11) | 0.0025 (10) | 0.0025 (9) | −0.0007 (9) |
C8 | 0.0550 (12) | 0.0595 (12) | 0.0390 (10) | −0.0038 (11) | −0.0032 (9) | 0.0082 (9) |
C1 | 0.0760 (16) | 0.0665 (15) | 0.0574 (14) | −0.0186 (13) | 0.0093 (13) | −0.0013 (12) |
C5 | 0.0687 (15) | 0.0663 (14) | 0.0482 (12) | −0.0117 (12) | −0.0022 (11) | 0.0102 (11) |
C4 | 0.0887 (18) | 0.0749 (16) | 0.0446 (12) | −0.0011 (15) | −0.0037 (13) | 0.0086 (12) |
C2 | 0.095 (2) | 0.0792 (18) | 0.0711 (17) | −0.0236 (16) | 0.0268 (16) | 0.0107 (14) |
C3 | 0.102 (2) | 0.0694 (16) | 0.0502 (14) | 0.0049 (16) | 0.0196 (14) | 0.0137 (12) |
O1—C9 | 1.241 (2) | C15—H15 | 0.93 |
O2—C13 | 1.348 (2) | C14—H14 | 0.93 |
O2—H2A | 0.82 | C12—H12 | 0.93 |
C10—C11 | 1.396 (3) | C7—C8 | 1.324 (3) |
C10—C15 | 1.398 (3) | C7—H7 | 0.93 |
C10—C9 | 1.468 (3) | C8—H8 | 0.93 |
C6—C5 | 1.383 (3) | C1—C2 | 1.386 (3) |
C6—C1 | 1.384 (3) | C1—H1 | 0.93 |
C6—C7 | 1.468 (3) | C5—C4 | 1.385 (3) |
C9—C8 | 1.475 (3) | C5—H5 | 0.93 |
C11—C12 | 1.371 (3) | C4—C3 | 1.360 (4) |
C11—H11 | 0.93 | C4—H4 | 0.93 |
C13—C14 | 1.389 (3) | C2—C3 | 1.367 (4) |
C13—C12 | 1.392 (3) | C2—H2 | 0.93 |
C15—C14 | 1.377 (3) | C3—H3 | 0.93 |
C13—O2—H2A | 109.5 | C11—C12—H12 | 120.0 |
C11—C10—C15 | 117.61 (19) | C13—C12—H12 | 120.0 |
C11—C10—C9 | 122.00 (18) | C8—C7—C6 | 126.6 (2) |
C15—C10—C9 | 120.39 (18) | C8—C7—H7 | 116.7 |
C5—C6—C1 | 117.9 (2) | C6—C7—H7 | 116.7 |
C5—C6—C7 | 122.47 (19) | C7—C8—C9 | 122.4 (2) |
C1—C6—C7 | 119.7 (2) | C7—C8—H8 | 118.8 |
O1—C9—C10 | 121.17 (18) | C9—C8—H8 | 118.8 |
O1—C9—C8 | 120.15 (19) | C6—C1—C2 | 121.0 (3) |
C10—C9—C8 | 118.68 (18) | C6—C1—H1 | 119.5 |
C12—C11—C10 | 121.63 (19) | C2—C1—H1 | 119.5 |
C12—C11—H11 | 119.2 | C6—C5—C4 | 120.9 (2) |
C10—C11—H11 | 119.2 | C6—C5—H5 | 119.6 |
O2—C13—C14 | 122.98 (18) | C4—C5—H5 | 119.6 |
O2—C13—C12 | 117.64 (19) | C3—C4—C5 | 120.2 (2) |
C14—C13—C12 | 119.4 (2) | C3—C4—H4 | 119.9 |
C14—C15—C10 | 121.24 (19) | C5—C4—H4 | 119.9 |
C14—C15—H15 | 119.4 | C3—C2—C1 | 119.9 (3) |
C10—C15—H15 | 119.4 | C3—C2—H2 | 120.0 |
C15—C14—C13 | 120.14 (18) | C1—C2—H2 | 120.0 |
C15—C14—H14 | 119.9 | C4—C3—C2 | 120.2 (2) |
C13—C14—H14 | 119.9 | C4—C3—H3 | 119.9 |
C11—C12—C13 | 120.0 (2) | C2—C3—H3 | 119.9 |
C11—C10—C9—O1 | 155.7 (2) | C5—C6—C7—C8 | −7.8 (4) |
C15—C10—C9—O1 | −24.4 (3) | C1—C6—C7—C8 | 170.5 (2) |
C11—C10—C9—C8 | −24.2 (3) | C6—C7—C8—C9 | −177.17 (19) |
C15—C10—C9—C8 | 155.73 (19) | O1—C9—C8—C7 | −11.4 (3) |
C15—C10—C11—C12 | 0.6 (3) | C10—C9—C8—C7 | 168.5 (2) |
C9—C10—C11—C12 | −179.4 (2) | C5—C6—C1—C2 | 1.5 (4) |
C11—C10—C15—C14 | 0.8 (3) | C7—C6—C1—C2 | −176.9 (2) |
C9—C10—C15—C14 | −179.15 (18) | C1—C6—C5—C4 | −1.2 (4) |
C10—C15—C14—C13 | −1.7 (3) | C7—C6—C5—C4 | 177.1 (2) |
O2—C13—C14—C15 | −179.4 (2) | C6—C5—C4—C3 | 0.7 (4) |
C12—C13—C14—C15 | 1.2 (3) | C6—C1—C2—C3 | −1.2 (4) |
C10—C11—C12—C13 | −1.1 (3) | C5—C4—C3—C2 | −0.3 (4) |
O2—C13—C12—C11 | −179.3 (2) | C1—C2—C3—C4 | 0.6 (4) |
C14—C13—C12—C11 | 0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.90 | 2.704 (2) | 168 |
C7—H7···O1 | 0.93 | 2.49 | 2.816 (3) | 101 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H12O2 |
Mr | 224.25 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 8.4663 (10), 22.384 (2), 12.216 (3) |
V (Å3) | 2315.2 (6) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.30 × 0.22 × 0.15 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.822, 0.905 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2107, 2107, 1518 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.129, 1.09 |
No. of reflections | 2107 |
No. of parameters | 156 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.14 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.90 | 2.704 (2) | 168.3 |
C7—H7···O1 | 0.93 | 2.49 | 2.816 (3) | 100.7 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
It is well known that in ketones, the carbonyl group plays an important role in the antibacterial activity of chalcones. Earlier crystal structure studies of some of the α,β-unsaturated ketone derivatives (Shanmuga Sundara Raj et al., 1996, 1998) have shown that there are two possible conformational isomers of ketones, one corresponds to the s-cis and the other to the s-trans form.
The title compound, (I), assumes an s-cis conformation, as can be seen from the torsion angle C7—C8—C9—O1 of -11.4 (3)°. The dihedral angle between the 4-hydroxyphenyl and phenyl rings is 34.96 (10)°. The central –CH═CH—C(═O)- group is oriented at angles of 13.04 (19) and 25.19 (14)° with respect to the phenyl and 4-hydroxyphenyl rings, respectively. The lengths of the C6—C7 [1.468 (3) Å], C7—C8 [1.324 (3) Å], C8—C9 [1.475 (3) Å], C9—O1 [1.241 (2) Å] and C9—C10 [1.468 (3) Å] bonds indicate conjugation. The widening of the bond angle C6—C7—C8 to 126.6 (2)° may be due to the close approach (2.20 Å) of atoms H8 and H5. A slight increase in the bond angle C7—C8—C9 to 122.4 (2)° may be attributed to the short intramolecular non-bonded interaction between O1 and H7 (2.49 Å). The unsaturated ketone group is not strictly planar, as is evident from the torsion angles C15—C10—C9—C8 [155.73 (19)°], C10—C9—C8—C7 [168.50 (2)°], C9—C8—C7—C6 [-177.17 (19)°] and C8—C7—C6—C1 [170.50 (2)°]. The H atoms H7 and H8 are trans to each other. The crystal structure is stabilized by O—H···O-type intermolecular hydrogen bonds (Table 1).