In the title compound, alternatively called 1-(2-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one, C
15H
12O
3, 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
CCDC reference: 170910
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
All H atoms were located from difference Fourier map and refined isotropically.
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.
Crystal data top
C15H12O3 | F(000) = 1008 |
Mr = 240.25 | Dx = 1.349 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 23.630 (5) Å | θ = 11.0–11.5° |
b = 5.582 (2) Å | µ = 0.09 mm−1 |
c = 18.004 (6) Å | T = 298 K |
β = 95.04 (2)° | Plate, yellow |
V = 2365.4 (12) Å3 | 0.30 × 0.25 × 0.10 mm |
Z = 8 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.019 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.0° |
Graphite monochromator | h = −30→30 |
ω–2θ scans | k = 0→7 |
2812 measured reflections | l = 0→23 |
2719 independent reflections | 3 standard reflections every 97 reflections |
1824 reflections with I > 2σ(I) | intensity decay: 0.8% |
Refinement top
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.048 | Weighting 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 = 1.17 | Δρmax = 0.24 e Å−3 |
2718 reflections | Δρmin = −0.19 e Å−3 |
212 parameters | Extinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213. |
0 restraints | Extinction coefficient: 4.8E-7 (9) |
Crystal data top
C15H12O3 | V = 2365.4 (12) Å3 |
Mr = 240.25 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.630 (5) Å | µ = 0.09 mm−1 |
b = 5.582 (2) Å | T = 298 K |
c = 18.004 (6) Å | 0.30 × 0.25 × 0.10 mm |
β = 95.04 (2)° | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.019 |
2812 measured reflections | 3 standard reflections every 97 reflections |
2719 independent reflections | intensity decay: 0.8% |
1824 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.129 | All H-atom parameters refined |
S = 1.17 | Δρmax = 0.24 e Å−3 |
2718 reflections | Δρmin = −0.19 e Å−3 |
212 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.39992 (4) | 0.14556 (18) | 0.08456 (6) | 0.0555 (3) | |
O2 | 0.30951 (5) | 0.0103 (2) | 0.14146 (8) | 0.0697 (4) | |
O3 | 0.56842 (5) | 0.5006 (2) | 0.01064 (7) | 0.0645 (4) | |
C1 | 0.42843 (6) | −0.0153 (3) | 0.11815 (8) | 0.0457 (4) | |
C2 | 0.49003 (6) | −0.0275 (3) | 0.11526 (9) | 0.0548 (5) | |
C3 | 0.51974 (6) | 0.1400 (3) | 0.08475 (8) | 0.0458 (4) | |
C4 | 0.39992 (6) | −0.1917 (3) | 0.16317 (7) | 0.0452 (4) | |
C5 | 0.34157 (6) | −0.1668 (3) | 0.17308 (8) | 0.0509 (4) | |
C6 | 0.31553 (7) | −0.3311 (4) | 0.21797 (9) | 0.0625 (5) | |
C7 | 0.34594 (8) | −0.5147 (3) | 0.25190 (9) | 0.0643 (5) | |
C8 | 0.40283 (8) | −0.5444 (3) | 0.24205 (9) | 0.0624 (5) | |
C9 | 0.42887 (7) | −0.3852 (3) | 0.19824 (9) | 0.0540 (5) | |
C10 | 0.58107 (5) | 0.1446 (2) | 0.07967 (7) | 0.0422 (4) | |
C11 | 0.60452 (6) | 0.3325 (3) | 0.04089 (8) | 0.0449 (4) | |
C12 | 0.66281 (6) | 0.3426 (3) | 0.03453 (9) | 0.0514 (4) | |
C13 | 0.69739 (6) | 0.1650 (3) | 0.06576 (9) | 0.0564 (5) | |
C14 | 0.67531 (7) | −0.0225 (3) | 0.10406 (9) | 0.0568 (5) | |
C15 | 0.61762 (6) | −0.0308 (3) | 0.11090 (9) | 0.0506 (4) | |
H2 | 0.5091 (7) | −0.156 (3) | 0.1361 (10) | 0.080 (6)* | |
H3 | 0.4994 (7) | 0.269 (3) | 0.0652 (9) | 0.067 (5)* | |
H6 | 0.2759 (7) | −0.306 (3) | 0.2201 (10) | 0.081 (6)* | |
H7 | 0.3276 (8) | −0.624 (3) | 0.2819 (11) | 0.080 (6)* | |
H8 | 0.4240 (7) | −0.681 (3) | 0.2664 (10) | 0.080 (6)* | |
H9 | 0.4672 (7) | −0.414 (3) | 0.1898 (9) | 0.059 (5)* | |
H12 | 0.6774 (7) | 0.479 (3) | 0.0068 (9) | 0.065 (5)* | |
H13 | 0.7375 (7) | 0.175 (3) | 0.0614 (9) | 0.073 (5)* | |
H14 | 0.6994 (6) | −0.144 (3) | 0.1252 (9) | 0.060 (5)* | |
H15 | 0.6043 (6) | −0.157 (3) | 0.1382 (9) | 0.059 (5)* | |
H21 | 0.3321 (9) | 0.095 (4) | 0.1149 (12) | 0.094 (7)* | |
H31 | 0.5834 (8) | 0.604 (3) | −0.0145 (11) | 0.076 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0493 (6) | 0.0572 (7) | 0.0605 (6) | −0.0075 (5) | 0.0072 (5) | 0.0113 (6) |
O2 | 0.0462 (6) | 0.0741 (8) | 0.0895 (9) | −0.0078 (6) | 0.0109 (6) | 0.0118 (7) |
O3 | 0.0479 (6) | 0.0569 (7) | 0.0896 (9) | −0.0036 (6) | 0.0108 (6) | 0.0315 (7) |
C1 | 0.0470 (7) | 0.0471 (8) | 0.0436 (7) | −0.0086 (7) | 0.0075 (6) | −0.0026 (7) |
C2 | 0.0474 (8) | 0.0526 (9) | 0.0657 (10) | −0.0037 (8) | 0.0118 (7) | 0.0106 (8) |
C3 | 0.0442 (8) | 0.0487 (8) | 0.0446 (8) | −0.0054 (7) | 0.0044 (6) | 0.0046 (7) |
C4 | 0.0460 (7) | 0.0475 (8) | 0.0429 (7) | −0.0121 (7) | 0.0078 (6) | −0.0032 (6) |
C5 | 0.0475 (8) | 0.0543 (9) | 0.0508 (8) | −0.0139 (7) | 0.0046 (7) | −0.0042 (7) |
C6 | 0.0519 (9) | 0.0780 (12) | 0.0591 (10) | −0.0250 (9) | 0.0140 (8) | −0.0045 (9) |
C7 | 0.0765 (11) | 0.0677 (11) | 0.0503 (9) | −0.0307 (10) | 0.0140 (8) | 0.0054 (9) |
C8 | 0.0737 (11) | 0.0597 (10) | 0.0545 (9) | −0.0118 (9) | 0.0104 (8) | 0.0090 (8) |
C9 | 0.0558 (9) | 0.0568 (9) | 0.0505 (8) | −0.0072 (8) | 0.0108 (7) | 0.0022 (8) |
C10 | 0.0417 (7) | 0.0451 (8) | 0.0404 (7) | −0.0057 (6) | 0.0067 (6) | −0.0023 (6) |
C11 | 0.0438 (7) | 0.0453 (8) | 0.0459 (7) | −0.0041 (7) | 0.0048 (6) | 0.0019 (7) |
C12 | 0.0468 (8) | 0.0543 (9) | 0.0547 (9) | −0.0095 (7) | 0.0129 (7) | 0.0036 (8) |
C13 | 0.0416 (8) | 0.0716 (11) | 0.0574 (9) | −0.0021 (8) | 0.0113 (7) | −0.0017 (8) |
C14 | 0.0498 (8) | 0.0620 (10) | 0.0587 (9) | 0.0071 (8) | 0.0046 (7) | 0.0058 (8) |
C15 | 0.0518 (8) | 0.0503 (9) | 0.0504 (8) | −0.0033 (7) | 0.0076 (7) | 0.0080 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.2467 (18) | C7—C8 | 1.381 (3) |
O2—C5 | 1.341 (2) | C7—H7 | 0.94 (2) |
O2—H21 | 0.89 (2) | C8—C9 | 1.370 (2) |
O3—C11 | 1.3500 (18) | C8—H8 | 0.99 (2) |
O3—H31 | 0.83 (2) | C9—H9 | 0.946 (17) |
C1—C2 | 1.462 (2) | C10—C11 | 1.401 (2) |
C1—C4 | 1.475 (2) | C10—C15 | 1.391 (2) |
C2—C3 | 1.318 (2) | C11—C12 | 1.393 (2) |
C2—H2 | 0.91 (2) | C12—C13 | 1.373 (2) |
C3—C10 | 1.460 (2) | C12—H12 | 0.989 (19) |
C3—H3 | 0.918 (18) | C13—C14 | 1.381 (3) |
C4—C5 | 1.413 (2) | C13—H13 | 0.960 (18) |
C4—C9 | 1.399 (2) | C14—C15 | 1.380 (2) |
C5—C6 | 1.400 (2) | C14—H14 | 0.943 (18) |
C6—C7 | 1.365 (3) | C15—H15 | 0.929 (17) |
C6—H6 | 0.950 (18) | | |
| | | |
O1···C8i | 3.318 (2) | O3···C15i | 3.329 (2) |
O1···C9i | 3.357 (2) | H3···H31ii | 2.20 (3) |
O2···C7i | 3.380 (3) | | |
| | | |
C5—O2—H21 | 106.1 (14) | C7—C8—H8 | 119.6 (11) |
C11—O3—H31 | 114.8 (13) | C9—C8—H8 | 121.2 (11) |
O1—C1—C2 | 120.88 (14) | C4—C9—C8 | 122.28 (17) |
O1—C1—C4 | 119.58 (13) | C4—C9—H9 | 119.8 (10) |
C2—C1—C4 | 119.52 (14) | C8—C9—H9 | 117.8 (11) |
C1—C2—C3 | 123.39 (17) | C3—C10—C11 | 118.85 (14) |
C1—C2—H2 | 118.7 (12) | C3—C10—C15 | 123.14 (13) |
C3—C2—H2 | 117.9 (12) | C11—C10—C15 | 118.01 (13) |
C2—C3—C10 | 127.35 (16) | O3—C11—C10 | 117.24 (13) |
C2—C3—H3 | 115.9 (11) | O3—C11—C12 | 122.20 (14) |
C10—C3—H3 | 116.8 (11) | C10—C11—C12 | 120.56 (14) |
C1—C4—C5 | 120.13 (14) | C11—C12—C13 | 119.62 (15) |
C1—C4—C9 | 122.29 (14) | C11—C12—H12 | 117.6 (10) |
C5—C4—C9 | 117.57 (14) | C13—C12—H12 | 122.8 (10) |
O2—C5—C4 | 122.68 (14) | C12—C13—C14 | 120.94 (15) |
O2—C5—C6 | 117.86 (15) | C12—C13—H13 | 118.9 (11) |
C4—C5—C6 | 119.46 (16) | C14—C13—H13 | 120.2 (11) |
C5—C6—C7 | 120.63 (17) | C13—C14—C15 | 119.32 (17) |
C5—C6—H6 | 114.3 (12) | C13—C14—H14 | 120.3 (10) |
C7—C6—H6 | 125.0 (12) | C15—C14—H14 | 120.4 (10) |
C6—C7—C8 | 120.84 (17) | C10—C15—C14 | 121.55 (16) |
C6—C7—H7 | 119.3 (12) | C10—C15—H15 | 121.4 (10) |
C8—C7—H7 | 119.8 (12) | C14—C15—H15 | 117.0 (10) |
C7—C8—C9 | 119.19 (19) | | |
| | | |
O1—C1—C2—C3 | 7.5 (3) | C3—C2—C1—C4 | −170.77 (15) |
O1—C1—C4—C5 | −5.2 (2) | C3—C10—C11—C12 | −179.71 (14) |
O1—C1—C4—C9 | 175.81 (14) | C3—C10—C15—C14 | 179.05 (15) |
O2—C5—C4—C1 | 1.7 (2) | C4—C5—C6—C7 | −0.2 (3) |
O2—C5—C4—C9 | −179.26 (14) | C4—C9—C8—C7 | 0.4 (3) |
O2—C5—C6—C7 | −179.75 (15) | C5—C4—C9—C8 | −1.3 (2) |
O3—C11—C10—C3 | 0.4 (2) | C5—C6—C7—C8 | −0.8 (3) |
O3—C11—C10—C15 | 179.70 (14) | C6—C5—C4—C9 | 1.2 (2) |
O3—C11—C12—C13 | −179.27 (15) | C6—C7—C8—C9 | 0.7 (3) |
C1—C2—C3—C10 | 179.53 (15) | C10—C11—C12—C13 | 0.8 (2) |
C1—C4—C5—C6 | −177.92 (14) | C10—C15—C14—C13 | 0.4 (3) |
C1—C4—C9—C8 | 177.78 (15) | C11—C10—C15—C14 | −0.2 (2) |
C2—C1—C4—C5 | 173.11 (14) | C11—C12—C13—C14 | −0.7 (3) |
C2—C1—C4—C9 | −5.9 (2) | C12—C11—C10—C15 | −0.4 (2) |
C2—C3—C10—C11 | 176.16 (17) | C12—C13—C14—C15 | 0.0 (3) |
C2—C3—C10—C15 | −3.1 (3) | | |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H21···O1 | 0.89 (2) | 1.76 (2) | 2.5630 (17) | 150 (2) |
O3—H31···O1ii | 0.83 (2) | 1.95 (2) | 2.7610 (18) | 166 (2) |
C3—H3···O3ii | 0.92 (2) | 2.39 (2) | 3.269 (2) | 161 (2) |
Symmetry code: (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C15H12O3 |
Mr | 240.25 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 23.630 (5), 5.582 (2), 18.004 (6) |
β (°) | 95.04 (2) |
V (Å3) | 2365.4 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.10 |
|
Data collection |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2812, 2719, 1824 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.129, 1.17 |
No. of reflections | 2718 |
No. of parameters | 212 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 |
Selected geometric parameters (Å, º) topO1—C1 | 1.2467 (18) | C6—C7 | 1.365 (3) |
O2—C5 | 1.341 (2) | C7—C8 | 1.381 (3) |
O3—C11 | 1.3500 (18) | C8—C9 | 1.370 (2) |
C1—C2 | 1.462 (2) | C10—C11 | 1.401 (2) |
C1—C4 | 1.475 (2) | C10—C15 | 1.391 (2) |
C2—C3 | 1.318 (2) | C11—C12 | 1.393 (2) |
C3—C10 | 1.460 (2) | C12—C13 | 1.373 (2) |
C4—C5 | 1.413 (2) | C13—C14 | 1.381 (3) |
C4—C9 | 1.399 (2) | C14—C15 | 1.380 (2) |
C5—C6 | 1.400 (2) | | |
| | | |
O1—C1—C2 | 120.88 (14) | C7—C8—C9 | 119.19 (19) |
O1—C1—C4 | 119.58 (13) | C4—C9—C8 | 122.28 (17) |
C2—C1—C4 | 119.52 (14) | C3—C10—C11 | 118.85 (14) |
C1—C2—C3 | 123.39 (17) | C3—C10—C15 | 123.14 (13) |
C2—C3—C10 | 127.35 (16) | C11—C10—C15 | 118.01 (13) |
C1—C4—C5 | 120.13 (14) | O3—C11—C10 | 117.24 (13) |
C1—C4—C9 | 122.29 (14) | O3—C11—C12 | 122.20 (14) |
C5—C4—C9 | 117.57 (14) | C10—C11—C12 | 120.56 (14) |
O2—C5—C4 | 122.68 (14) | C11—C12—C13 | 119.62 (15) |
O2—C5—C6 | 117.86 (15) | C12—C13—C14 | 120.94 (15) |
C4—C5—C6 | 119.46 (16) | C13—C14—C15 | 119.32 (17) |
C5—C6—C7 | 120.63 (17) | C10—C15—C14 | 121.55 (16) |
C6—C7—C8 | 120.84 (17) | | |
| | | |
C1—C2—C3—C10 | 179.53 (15) | C2—C3—C10—C11 | 176.16 (17) |
C2—C1—C4—C5 | 173.11 (14) | C3—C2—C1—C4 | −170.77 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H21···O1 | 0.89 (2) | 1.76 (2) | 2.5630 (17) | 150 (2) |
O3—H31···O1i | 0.83 (2) | 1.95 (2) | 2.7610 (18) | 166.4 (19) |
C3—H3···O3i | 0.918 (18) | 2.388 (18) | 3.269 (2) | 160.7 (15) |
Symmetry code: (i) −x+1, −y+1, −z. |
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 C═C 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).