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In the title compound, alternatively called 1-(2-hydroxy­phenyl)-3-(2-hydroxy­phenyl)-2-propen-1-one, C15H12O3, inter­molecular O—H...O hydrogen bonds are formed between mol­ecules related by a center of symmetry, and the dimer is planar as a whole. The dimers are stacked along the shortest axis to form a column. In the column, the C=C double bonds related by another center of symmetry approach the shortest C...C distance of 3.482 Å. The intermolecular hydrogen bonds and a chevron structure in the crystal may prohibit topochemical reaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011898/om6036sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011898/om6036Isup2.hkl
Contains datablock I

CCDC reference: 170910

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.129
  • Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Some chalcones are known to be photoreactive in solid state, e.g. 4-methoxychalcone (Rabinovich & Schmidt, 1970) and one of the six polymorphs of chalcone (Montaudo & Caccamese, 1973). We carried out the present study as part of topochemical study (Iwamoto & Kashino, 1993; Kanao et al., 1990). After completion of the structure determination for the title compound, (I), we noticed that substantially the same structure has already been reported by Feng et al. (1999). However, they could only determine the structure with poor precision because good quality of crystals were not available at the time. We report here the crystal structure of (I), determined with significantly higher precision than before.

An intramolecular O2—H21···O1 hydrogen bond is formed in (I) (Fig. 1) and the molecule is roughly planar, as seen from the torsion angles in Table 1. The molecules related by a center of symmetry at Wyckoff position 4a form a dimer linked by an O3—H31···O1i hydrogen bond [symmetry code: (i) 1 - x, 1 - y, -z] (Fig. 1 and Table 2). The dimer lies on (014). The dimers are stacked along b to form a column. The columns related by a twofold screw axis form a chevron.

In the column, the CC double bonds of the molecules related by a center of symmetry at Wyckoff position 4 b approach to give a shortest C···C distance of C3···C3ii = 3.482 Å [symmetry code: (ii) 1 - x, -y, -z]. However, this is not an optimal contact for photodimerization to occur, because the C2ii atom does not make a short contact with the C3 atom. The mode of molecular overlapping shows that the molecule at (ii) should be displaced along the C2—C3 bond by about 1.3 Å relative to the original molecule in order to realise the shortest contact between atoms C3 and C2ii. Such a displacement may be prohibited, because it causes breakdown of the intermolecular hydrogen bonds and the chevron structure formed in the crystal. We could not observe any indication of the photoreaction in the rotation and Weissenerg photographs of the crystals taken after exposing the specimens to sunlight for one month (the method of light exposure used by Cohen et al. (1964).

Experimental top

Compound (I) was prepared by the reaction of 2-hydroxyacetophenone and 2-hydroxybenzaldehyde according to the method described by Alcantara et al. (1987). Crystals were grown from an ethanol solution by slow evaporation.

Refinement top

All H atoms were located from difference Fourier map and refined isotropically.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN for Windows; software used to prepare material for publication: TEXSAN for Windows.

Figures top
[Figure 1] Fig. 1. A molecular view of the title compound showing the hydrogen-bonding pattern and the atomic numbering scheme for the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are indicated by dashed lines (Farrugia, 1997). [Symmetry code: (i) 1 - x, 1 - y, -z.]
(I) top
Crystal data top
C15H12O3F(000) = 1008
Mr = 240.25Dx = 1.349 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 23.630 (5) Åθ = 11.0–11.5°
b = 5.582 (2) ŵ = 0.09 mm1
c = 18.004 (6) ÅT = 298 K
β = 95.04 (2)°Plate, yellow
V = 2365.4 (12) Å30.30 × 0.25 × 0.10 mm
Z = 8
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.019
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.0°
Graphite monochromatorh = 3030
ω–2θ scansk = 07
2812 measured reflectionsl = 023
2719 independent reflections3 standard reflections every 97 reflections
1824 reflections with I > 2σ(I) intensity decay: 0.8%
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.048Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.0009|Fo|2]
wR(F2) = 0.129(Δ/σ)max = 0.01
S = 1.17Δρmax = 0.24 e Å3
2718 reflectionsΔρmin = 0.19 e Å3
212 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraintsExtinction coefficient: 4.8E-7 (9)
Crystal data top
C15H12O3V = 2365.4 (12) Å3
Mr = 240.25Z = 8
Monoclinic, C2/cMo Kα radiation
a = 23.630 (5) ŵ = 0.09 mm1
b = 5.582 (2) ÅT = 298 K
c = 18.004 (6) Å0.30 × 0.25 × 0.10 mm
β = 95.04 (2)°
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.019
2812 measured reflections3 standard reflections every 97 reflections
2719 independent reflections intensity decay: 0.8%
1824 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.129All H-atom parameters refined
S = 1.17Δρmax = 0.24 e Å3
2718 reflectionsΔρmin = 0.19 e Å3
212 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.39992 (4)0.14556 (18)0.08456 (6)0.0555 (3)
O20.30951 (5)0.0103 (2)0.14146 (8)0.0697 (4)
O30.56842 (5)0.5006 (2)0.01064 (7)0.0645 (4)
C10.42843 (6)0.0153 (3)0.11815 (8)0.0457 (4)
C20.49003 (6)0.0275 (3)0.11526 (9)0.0548 (5)
C30.51974 (6)0.1400 (3)0.08475 (8)0.0458 (4)
C40.39992 (6)0.1917 (3)0.16317 (7)0.0452 (4)
C50.34157 (6)0.1668 (3)0.17308 (8)0.0509 (4)
C60.31553 (7)0.3311 (4)0.21797 (9)0.0625 (5)
C70.34594 (8)0.5147 (3)0.25190 (9)0.0643 (5)
C80.40283 (8)0.5444 (3)0.24205 (9)0.0624 (5)
C90.42887 (7)0.3852 (3)0.19824 (9)0.0540 (5)
C100.58107 (5)0.1446 (2)0.07967 (7)0.0422 (4)
C110.60452 (6)0.3325 (3)0.04089 (8)0.0449 (4)
C120.66281 (6)0.3426 (3)0.03453 (9)0.0514 (4)
C130.69739 (6)0.1650 (3)0.06576 (9)0.0564 (5)
C140.67531 (7)0.0225 (3)0.10406 (9)0.0568 (5)
C150.61762 (6)0.0308 (3)0.11090 (9)0.0506 (4)
H20.5091 (7)0.156 (3)0.1361 (10)0.080 (6)*
H30.4994 (7)0.269 (3)0.0652 (9)0.067 (5)*
H60.2759 (7)0.306 (3)0.2201 (10)0.081 (6)*
H70.3276 (8)0.624 (3)0.2819 (11)0.080 (6)*
H80.4240 (7)0.681 (3)0.2664 (10)0.080 (6)*
H90.4672 (7)0.414 (3)0.1898 (9)0.059 (5)*
H120.6774 (7)0.479 (3)0.0068 (9)0.065 (5)*
H130.7375 (7)0.175 (3)0.0614 (9)0.073 (5)*
H140.6994 (6)0.144 (3)0.1252 (9)0.060 (5)*
H150.6043 (6)0.157 (3)0.1382 (9)0.059 (5)*
H210.3321 (9)0.095 (4)0.1149 (12)0.094 (7)*
H310.5834 (8)0.604 (3)0.0145 (11)0.076 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0493 (6)0.0572 (7)0.0605 (6)0.0075 (5)0.0072 (5)0.0113 (6)
O20.0462 (6)0.0741 (8)0.0895 (9)0.0078 (6)0.0109 (6)0.0118 (7)
O30.0479 (6)0.0569 (7)0.0896 (9)0.0036 (6)0.0108 (6)0.0315 (7)
C10.0470 (7)0.0471 (8)0.0436 (7)0.0086 (7)0.0075 (6)0.0026 (7)
C20.0474 (8)0.0526 (9)0.0657 (10)0.0037 (8)0.0118 (7)0.0106 (8)
C30.0442 (8)0.0487 (8)0.0446 (8)0.0054 (7)0.0044 (6)0.0046 (7)
C40.0460 (7)0.0475 (8)0.0429 (7)0.0121 (7)0.0078 (6)0.0032 (6)
C50.0475 (8)0.0543 (9)0.0508 (8)0.0139 (7)0.0046 (7)0.0042 (7)
C60.0519 (9)0.0780 (12)0.0591 (10)0.0250 (9)0.0140 (8)0.0045 (9)
C70.0765 (11)0.0677 (11)0.0503 (9)0.0307 (10)0.0140 (8)0.0054 (9)
C80.0737 (11)0.0597 (10)0.0545 (9)0.0118 (9)0.0104 (8)0.0090 (8)
C90.0558 (9)0.0568 (9)0.0505 (8)0.0072 (8)0.0108 (7)0.0022 (8)
C100.0417 (7)0.0451 (8)0.0404 (7)0.0057 (6)0.0067 (6)0.0023 (6)
C110.0438 (7)0.0453 (8)0.0459 (7)0.0041 (7)0.0048 (6)0.0019 (7)
C120.0468 (8)0.0543 (9)0.0547 (9)0.0095 (7)0.0129 (7)0.0036 (8)
C130.0416 (8)0.0716 (11)0.0574 (9)0.0021 (8)0.0113 (7)0.0017 (8)
C140.0498 (8)0.0620 (10)0.0587 (9)0.0071 (8)0.0046 (7)0.0058 (8)
C150.0518 (8)0.0503 (9)0.0504 (8)0.0033 (7)0.0076 (7)0.0080 (7)
Geometric parameters (Å, º) top
O1—C11.2467 (18)C7—C81.381 (3)
O2—C51.341 (2)C7—H70.94 (2)
O2—H210.89 (2)C8—C91.370 (2)
O3—C111.3500 (18)C8—H80.99 (2)
O3—H310.83 (2)C9—H90.946 (17)
C1—C21.462 (2)C10—C111.401 (2)
C1—C41.475 (2)C10—C151.391 (2)
C2—C31.318 (2)C11—C121.393 (2)
C2—H20.91 (2)C12—C131.373 (2)
C3—C101.460 (2)C12—H120.989 (19)
C3—H30.918 (18)C13—C141.381 (3)
C4—C51.413 (2)C13—H130.960 (18)
C4—C91.399 (2)C14—C151.380 (2)
C5—C61.400 (2)C14—H140.943 (18)
C6—C71.365 (3)C15—H150.929 (17)
C6—H60.950 (18)
O1···C8i3.318 (2)O3···C15i3.329 (2)
O1···C9i3.357 (2)H3···H31ii2.20 (3)
O2···C7i3.380 (3)
C5—O2—H21106.1 (14)C7—C8—H8119.6 (11)
C11—O3—H31114.8 (13)C9—C8—H8121.2 (11)
O1—C1—C2120.88 (14)C4—C9—C8122.28 (17)
O1—C1—C4119.58 (13)C4—C9—H9119.8 (10)
C2—C1—C4119.52 (14)C8—C9—H9117.8 (11)
C1—C2—C3123.39 (17)C3—C10—C11118.85 (14)
C1—C2—H2118.7 (12)C3—C10—C15123.14 (13)
C3—C2—H2117.9 (12)C11—C10—C15118.01 (13)
C2—C3—C10127.35 (16)O3—C11—C10117.24 (13)
C2—C3—H3115.9 (11)O3—C11—C12122.20 (14)
C10—C3—H3116.8 (11)C10—C11—C12120.56 (14)
C1—C4—C5120.13 (14)C11—C12—C13119.62 (15)
C1—C4—C9122.29 (14)C11—C12—H12117.6 (10)
C5—C4—C9117.57 (14)C13—C12—H12122.8 (10)
O2—C5—C4122.68 (14)C12—C13—C14120.94 (15)
O2—C5—C6117.86 (15)C12—C13—H13118.9 (11)
C4—C5—C6119.46 (16)C14—C13—H13120.2 (11)
C5—C6—C7120.63 (17)C13—C14—C15119.32 (17)
C5—C6—H6114.3 (12)C13—C14—H14120.3 (10)
C7—C6—H6125.0 (12)C15—C14—H14120.4 (10)
C6—C7—C8120.84 (17)C10—C15—C14121.55 (16)
C6—C7—H7119.3 (12)C10—C15—H15121.4 (10)
C8—C7—H7119.8 (12)C14—C15—H15117.0 (10)
C7—C8—C9119.19 (19)
O1—C1—C2—C37.5 (3)C3—C2—C1—C4170.77 (15)
O1—C1—C4—C55.2 (2)C3—C10—C11—C12179.71 (14)
O1—C1—C4—C9175.81 (14)C3—C10—C15—C14179.05 (15)
O2—C5—C4—C11.7 (2)C4—C5—C6—C70.2 (3)
O2—C5—C4—C9179.26 (14)C4—C9—C8—C70.4 (3)
O2—C5—C6—C7179.75 (15)C5—C4—C9—C81.3 (2)
O3—C11—C10—C30.4 (2)C5—C6—C7—C80.8 (3)
O3—C11—C10—C15179.70 (14)C6—C5—C4—C91.2 (2)
O3—C11—C12—C13179.27 (15)C6—C7—C8—C90.7 (3)
C1—C2—C3—C10179.53 (15)C10—C11—C12—C130.8 (2)
C1—C4—C5—C6177.92 (14)C10—C15—C14—C130.4 (3)
C1—C4—C9—C8177.78 (15)C11—C10—C15—C140.2 (2)
C2—C1—C4—C5173.11 (14)C11—C12—C13—C140.7 (3)
C2—C1—C4—C95.9 (2)C12—C11—C10—C150.4 (2)
C2—C3—C10—C11176.16 (17)C12—C13—C14—C150.0 (3)
C2—C3—C10—C153.1 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H21···O10.89 (2)1.76 (2)2.5630 (17)150 (2)
O3—H31···O1ii0.83 (2)1.95 (2)2.7610 (18)166 (2)
C3—H3···O3ii0.92 (2)2.39 (2)3.269 (2)161 (2)
Symmetry code: (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H12O3
Mr240.25
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)23.630 (5), 5.582 (2), 18.004 (6)
β (°) 95.04 (2)
V3)2365.4 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.25 × 0.10
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2812, 2719, 1824
Rint0.019
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.129, 1.17
No. of reflections2718
No. of parameters212
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.24, 0.19

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997-1999), SAPI91 (Fan, 1991), TEXSAN for Windows.

Selected geometric parameters (Å, º) top
O1—C11.2467 (18)C6—C71.365 (3)
O2—C51.341 (2)C7—C81.381 (3)
O3—C111.3500 (18)C8—C91.370 (2)
C1—C21.462 (2)C10—C111.401 (2)
C1—C41.475 (2)C10—C151.391 (2)
C2—C31.318 (2)C11—C121.393 (2)
C3—C101.460 (2)C12—C131.373 (2)
C4—C51.413 (2)C13—C141.381 (3)
C4—C91.399 (2)C14—C151.380 (2)
C5—C61.400 (2)
O1—C1—C2120.88 (14)C7—C8—C9119.19 (19)
O1—C1—C4119.58 (13)C4—C9—C8122.28 (17)
C2—C1—C4119.52 (14)C3—C10—C11118.85 (14)
C1—C2—C3123.39 (17)C3—C10—C15123.14 (13)
C2—C3—C10127.35 (16)C11—C10—C15118.01 (13)
C1—C4—C5120.13 (14)O3—C11—C10117.24 (13)
C1—C4—C9122.29 (14)O3—C11—C12122.20 (14)
C5—C4—C9117.57 (14)C10—C11—C12120.56 (14)
O2—C5—C4122.68 (14)C11—C12—C13119.62 (15)
O2—C5—C6117.86 (15)C12—C13—C14120.94 (15)
C4—C5—C6119.46 (16)C13—C14—C15119.32 (17)
C5—C6—C7120.63 (17)C10—C15—C14121.55 (16)
C6—C7—C8120.84 (17)
C1—C2—C3—C10179.53 (15)C2—C3—C10—C11176.16 (17)
C2—C1—C4—C5173.11 (14)C3—C2—C1—C4170.77 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H21···O10.89 (2)1.76 (2)2.5630 (17)150 (2)
O3—H31···O1i0.83 (2)1.95 (2)2.7610 (18)166.4 (19)
C3—H3···O3i0.918 (18)2.388 (18)3.269 (2)160.7 (15)
Symmetry code: (i) x+1, y+1, z.
 

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