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The title compound, C
17H
18O
3, is a product of sodium hypochlorite-induced degradation of ipriflavone, a synthetic isoflavone, which, according to some reports, is effective for prevention and treatment of postmenopausal osteoporosis. The dioxyphenyl fragment of the title molecule is almost coplanar with the carbonyl group and approximately orthogonal to the phenyl plane of the 2-phenylethanone group [the dihedral angle is 73.37 (9)°]. The molecule is stabilized by an intramolecular O—H
O bond, which closes the almost planar six-membered pseudo-ring. There is a π–π interaction between the benzene rings of hydroxyisopropoxyphenyl groups of neighbouring molecules (centroid-to-centroid distance 3.673 Å), which links the molecules into infinite chains extending along the
c axis of the crystal.
Supporting information
CCDC reference: 272135
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.096
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies
outside the range 0.95 <> 1.05
Calculated value of mu = 0.085
Value of mu given = 0.080
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
1-(2-hydroxy-4-isopropoxyphenyl)-2-phenylethanone
top
Crystal data top
C17H18O3 | F(000) = 576 |
Mr = 270.31 | Dx = 1.250 Mg m−3 |
Monoclinic, P21/c | Melting point: 351 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.949 (4) Å | Cell parameters from 1340 reflections |
b = 13.366 (2) Å | θ = 2.8–22.0° |
c = 7.324 (8) Å | µ = 0.08 mm−1 |
β = 101.214 (8)° | T = 298 K |
V = 1435.5 (16) Å3 | Prism, colorless |
Z = 4 | 0.53 × 0.28 × 0.16 mm |
Data collection top
Bruker Smart-1000 CCD area detector diffractometer | 2523 independent reflections |
Radiation source: fine-focus sealed tube | 1363 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (North et al., 1968) | h = −11→17 |
Tmin = 0.956, Tmax = 0.987 | k = −15→15 |
7179 measured reflections | l = −8→8 |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3 |
2523 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | |
O1 | 0.46160 (9) | 0.07444 (9) | 0.0997 (2) | 0.0553 (5) | |
H1O | 0.5118 | 0.0906 | 0.0801 | 0.083* | |
O2 | 0.58939 (9) | 0.19553 (10) | 0.0516 (2) | 0.0496 (5) | |
O3 | 0.18460 (9) | 0.21920 (10) | 0.2001 (2) | 0.0476 (4) | |
C1 | 0.41295 (14) | 0.15793 (14) | 0.1211 (3) | 0.0374 (6) | |
C2 | 0.45041 (14) | 0.25472 (14) | 0.1137 (3) | 0.0342 (5) | |
C3 | 0.39284 (14) | 0.33516 (14) | 0.1354 (3) | 0.0408 (6) | |
H3 | 0.4149 | 0.4000 | 0.1318 | 0.049* | |
C4 | 0.30567 (14) | 0.32162 (15) | 0.1617 (3) | 0.0416 (6) | |
H4 | 0.2692 | 0.3766 | 0.1739 | 0.050* | |
C5 | 0.27145 (14) | 0.22447 (15) | 0.1703 (3) | 0.0376 (6) | |
C6 | 0.32518 (14) | 0.14353 (15) | 0.1500 (3) | 0.0394 (6) | |
H6 | 0.3026 | 0.0790 | 0.1558 | 0.047* | |
C7 | 0.54311 (15) | 0.26790 (16) | 0.0834 (3) | 0.0390 (6) | |
C8 | 0.58325 (14) | 0.37265 (14) | 0.0897 (3) | 0.0484 (6) | |
H8B | 0.5516 | 0.4100 | −0.0171 | 0.058* | |
H8A | 0.5723 | 0.4062 | 0.2008 | 0.058* | |
C9 | 0.68424 (15) | 0.37473 (15) | 0.0900 (4) | 0.0445 (6) | |
C10 | 0.71758 (17) | 0.40314 (16) | −0.0647 (4) | 0.0543 (7) | |
H10 | 0.6771 | 0.4226 | −0.1718 | 0.065* | |
C11 | 0.8104 (2) | 0.40323 (18) | −0.0636 (4) | 0.0660 (8) | |
H11 | 0.8317 | 0.4238 | −0.1687 | 0.079* | |
C12 | 0.87060 (19) | 0.37306 (18) | 0.0917 (5) | 0.0720 (9) | |
H12 | 0.9328 | 0.3718 | 0.0919 | 0.086* | |
C13 | 0.83852 (18) | 0.34453 (18) | 0.2474 (5) | 0.0713 (9) | |
H13 | 0.8792 | 0.3244 | 0.3538 | 0.086* | |
C14 | 0.74587 (17) | 0.34568 (16) | 0.2462 (4) | 0.0589 (7) | |
H14 | 0.7248 | 0.3265 | 0.3525 | 0.071* | |
C15 | 0.14078 (14) | 0.12209 (15) | 0.1972 (3) | 0.0473 (6) | |
H15 | 0.1834 | 0.0740 | 0.2680 | 0.057* | |
C16 | 0.06113 (15) | 0.13765 (18) | 0.2934 (4) | 0.0689 (8) | |
H16A | 0.0832 | 0.1602 | 0.4185 | 0.103* | |
H16B | 0.0289 | 0.0757 | 0.2959 | 0.103* | |
H16C | 0.0207 | 0.1869 | 0.2270 | 0.103* | |
C17 | 0.11203 (16) | 0.08607 (18) | −0.0012 (4) | 0.0691 (8) | |
H17A | 0.1650 | 0.0776 | −0.0556 | 0.104* | |
H17B | 0.0721 | 0.1345 | −0.0717 | 0.104* | |
H17C | 0.0807 | 0.0233 | −0.0022 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0478 (10) | 0.0389 (8) | 0.0850 (14) | 0.0021 (8) | 0.0269 (9) | −0.0054 (9) |
O2 | 0.0420 (10) | 0.0444 (9) | 0.0658 (13) | 0.0005 (8) | 0.0186 (8) | −0.0048 (8) |
O3 | 0.0376 (10) | 0.0448 (9) | 0.0632 (13) | −0.0039 (7) | 0.0171 (8) | −0.0008 (8) |
C1 | 0.0393 (14) | 0.0377 (12) | 0.0357 (16) | 0.0038 (11) | 0.0086 (11) | −0.0028 (11) |
C2 | 0.0358 (14) | 0.0350 (12) | 0.0324 (15) | −0.0007 (10) | 0.0085 (11) | −0.0015 (10) |
C3 | 0.0453 (15) | 0.0349 (11) | 0.0430 (17) | −0.0050 (11) | 0.0103 (12) | −0.0007 (11) |
C4 | 0.0422 (15) | 0.0360 (12) | 0.0482 (18) | 0.0024 (11) | 0.0127 (12) | −0.0016 (11) |
C5 | 0.0344 (14) | 0.0438 (13) | 0.0355 (16) | −0.0021 (11) | 0.0090 (11) | −0.0013 (11) |
C6 | 0.0399 (14) | 0.0341 (12) | 0.0456 (17) | −0.0066 (11) | 0.0116 (11) | −0.0019 (11) |
C7 | 0.0391 (15) | 0.0429 (13) | 0.0353 (16) | −0.0026 (11) | 0.0077 (11) | −0.0003 (11) |
C8 | 0.0453 (15) | 0.0414 (12) | 0.0607 (19) | −0.0032 (11) | 0.0161 (12) | −0.0011 (12) |
C9 | 0.0455 (16) | 0.0346 (12) | 0.0558 (19) | −0.0036 (11) | 0.0157 (14) | −0.0011 (12) |
C10 | 0.0557 (17) | 0.0490 (14) | 0.060 (2) | −0.0091 (13) | 0.0161 (14) | −0.0038 (13) |
C11 | 0.067 (2) | 0.0586 (16) | 0.083 (2) | −0.0109 (15) | 0.0417 (18) | −0.0045 (16) |
C12 | 0.0510 (19) | 0.0520 (16) | 0.121 (3) | −0.0027 (14) | 0.036 (2) | −0.0009 (18) |
C13 | 0.0504 (19) | 0.0603 (17) | 0.099 (3) | −0.0059 (14) | 0.0039 (17) | 0.0125 (17) |
C14 | 0.0531 (18) | 0.0562 (15) | 0.069 (2) | −0.0097 (13) | 0.0168 (15) | 0.0099 (14) |
C15 | 0.0384 (14) | 0.0425 (13) | 0.063 (2) | −0.0076 (11) | 0.0135 (13) | 0.0007 (13) |
C16 | 0.0482 (16) | 0.0697 (17) | 0.095 (2) | −0.0111 (13) | 0.0305 (15) | −0.0034 (16) |
C17 | 0.0618 (18) | 0.0701 (16) | 0.073 (2) | −0.0177 (14) | 0.0069 (15) | −0.0087 (16) |
Geometric parameters (Å, º) top
O1—C1 | 1.357 (2) | C9—C14 | 1.378 (3) |
O1—H1O | 0.8200 | C10—C11 | 1.386 (3) |
O2—C7 | 1.237 (2) | C10—H10 | 0.9300 |
O3—C5 | 1.360 (3) | C11—C12 | 1.367 (4) |
O3—C15 | 1.452 (3) | C11—H11 | 0.9300 |
C1—C6 | 1.383 (3) | C12—C13 | 1.375 (4) |
C1—C2 | 1.415 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.405 (3) | C13—C14 | 1.383 (3) |
C2—C7 | 1.456 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.366 (3) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C17 | 1.511 (3) |
C4—C5 | 1.402 (3) | C15—C16 | 1.511 (3) |
C4—H4 | 0.9300 | C15—H15 | 0.9800 |
C5—C6 | 1.373 (3) | C16—H16A | 0.9600 |
C6—H6 | 0.9300 | C16—H16B | 0.9600 |
C7—C8 | 1.520 (3) | C16—H16C | 0.9600 |
C8—C9 | 1.510 (3) | C17—H17A | 0.9600 |
C8—H8B | 0.9700 | C17—H17B | 0.9600 |
C8—H8A | 0.9700 | C17—H17C | 0.9600 |
C9—C10 | 1.377 (3) | | |
| | | |
C1—O1—H1O | 109.5 | C9—C10—H10 | 119.4 |
C5—O3—C15 | 119.08 (16) | C11—C10—H10 | 119.4 |
O1—C1—C6 | 116.68 (18) | C12—C11—C10 | 120.1 (3) |
O1—C1—C2 | 121.5 (2) | C12—C11—H11 | 120.0 |
C6—C1—C2 | 121.83 (19) | C10—C11—H11 | 120.0 |
C3—C2—C1 | 116.1 (2) | C11—C12—C13 | 119.5 (3) |
C3—C2—C7 | 123.13 (19) | C11—C12—H12 | 120.2 |
C1—C2—C7 | 120.79 (18) | C13—C12—H12 | 120.2 |
C4—C3—C2 | 122.46 (19) | C12—C13—C14 | 120.1 (3) |
C4—C3—H3 | 118.8 | C12—C13—H13 | 119.9 |
C2—C3—H3 | 118.8 | C14—C13—H13 | 119.9 |
C3—C4—C5 | 119.71 (19) | C9—C14—C13 | 121.0 (3) |
C3—C4—H4 | 120.1 | C9—C14—H14 | 119.5 |
C5—C4—H4 | 120.1 | C13—C14—H14 | 119.5 |
O3—C5—C6 | 125.01 (19) | O3—C15—C17 | 110.01 (19) |
O3—C5—C4 | 115.06 (19) | O3—C15—C16 | 105.32 (18) |
C6—C5—C4 | 119.9 (2) | C17—C15—C16 | 112.9 (2) |
C5—C6—C1 | 119.98 (19) | O3—C15—H15 | 109.5 |
C5—C6—H6 | 120.0 | C17—C15—H15 | 109.5 |
C1—C6—H6 | 120.0 | C16—C15—H15 | 109.5 |
O2—C7—C2 | 121.18 (19) | C15—C16—H16A | 109.5 |
O2—C7—C8 | 119.6 (2) | C15—C16—H16B | 109.5 |
C2—C7—C8 | 119.24 (19) | H16A—C16—H16B | 109.5 |
C9—C8—C7 | 113.94 (18) | C15—C16—H16C | 109.5 |
C9—C8—H8B | 108.8 | H16A—C16—H16C | 109.5 |
C7—C8—H8B | 108.8 | H16B—C16—H16C | 109.5 |
C9—C8—H8A | 108.8 | C15—C17—H17A | 109.5 |
C7—C8—H8A | 108.8 | C15—C17—H17B | 109.5 |
H8B—C8—H8A | 107.7 | H17A—C17—H17B | 109.5 |
C10—C9—C14 | 118.1 (2) | C15—C17—H17C | 109.5 |
C10—C9—C8 | 121.7 (2) | H17A—C17—H17C | 109.5 |
C14—C9—C8 | 120.2 (2) | H17B—C17—H17C | 109.5 |
C9—C10—C11 | 121.2 (3) | | |
| | | |
O1—C1—C2—C3 | 179.23 (19) | C3—C2—C7—C8 | 4.8 (3) |
C6—C1—C2—C3 | −0.7 (3) | C1—C2—C7—C8 | −175.8 (2) |
O1—C1—C2—C7 | −0.2 (3) | O2—C7—C8—C9 | −10.6 (3) |
C6—C1—C2—C7 | 179.9 (2) | C2—C7—C8—C9 | 169.8 (2) |
C1—C2—C3—C4 | −0.2 (3) | C7—C8—C9—C10 | 106.4 (2) |
C7—C2—C3—C4 | 179.3 (2) | C7—C8—C9—C14 | −72.2 (3) |
C2—C3—C4—C5 | 0.9 (3) | C14—C9—C10—C11 | −0.4 (3) |
C15—O3—C5—C6 | −5.0 (3) | C8—C9—C10—C11 | −179.0 (2) |
C15—O3—C5—C4 | 175.38 (19) | C9—C10—C11—C12 | 1.2 (4) |
C3—C4—C5—O3 | 178.89 (19) | C10—C11—C12—C13 | −1.2 (4) |
C3—C4—C5—C6 | −0.8 (3) | C11—C12—C13—C14 | 0.5 (4) |
O3—C5—C6—C1 | −179.69 (19) | C10—C9—C14—C13 | −0.3 (3) |
C4—C5—C6—C1 | 0.0 (3) | C8—C9—C14—C13 | 178.3 (2) |
O1—C1—C6—C5 | −179.13 (19) | C12—C13—C14—C9 | 0.3 (4) |
C2—C1—C6—C5 | 0.8 (3) | C5—O3—C15—C17 | −75.7 (2) |
C3—C2—C7—O2 | −174.7 (2) | C5—O3—C15—C16 | 162.27 (19) |
C1—C2—C7—O2 | 4.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.82 | 1.86 | 2.580 (3) | 146 |
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