1-(2-Hydr­oxy-4-isopropoxyphen­yl)-2-phenyl­ethanone

Zhang, S.-P.; Wang, X.-B.; Zhang, Z.-T.

doi:10.1107/S1600536805010408

1-(2-Hydroxy-4-isopropoxyphenyl)-2-phenylethanone

The title compound, C₁₇H₁₈O₃, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010408/ya6236sup1.cif Contains datablocks I, 041014b
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010408/ya6236Isup2.hkl Contains datablock I

CCDC reference: 272135

checkCIF report

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

Computing details top

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
M_r = 270.31	D_x = 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	R_int = 0.047
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (North et al., 1968)	h = −11→17
T_min = 0.956, T_max = 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(F_o²) + (0.0342P)²] where P = (F_o² + 2F_c²)/3
2523 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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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1-(2-Hydr­oxy-4-isopropoxyphen­yl)-2-phenyl­ethanone

Supporting information

Key indicators

checkCIF/PLATON results

1-(2-Hydroxy-4-isopropoxyphenyl)-2-phenylethanone