1-(4-Benz-yloxy-2-hy-droxy-phen-yl)ethanone.

The title compound, C(15)H(14)O(3), has been obtained from the reaction of 2,4-dihy-droxy-acetophenone, potassium carbonate and benzyl bromide. The remaining hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond. In the crystal, inter-molecular C-H⋯O contacts occur.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ▶). For synthetic procedures for related compounds, see: Mendelson et al. (1996 ▶). For a related structure, see: Ma et al. (2010 ▶).

Experimental

Crystal data

C15H14O3

M = 242.26

Triclinic,

a = 5.8433 (7) Å

b = 8.0096 (8) Å

c = 13.8089 (13) Å

α = 74.061 (1)°

β = 84.589 (1)°

γ = 87.372 (2)°

V = 618.54 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.23 × 0.20 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.987

3169 measured reflections

2167 independent reflections

1291 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 1.02

2167 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104637X/im2328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104637X/im2328Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104637X/im2328Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14O3	Z = 2
Mr = 242.26	F(000) = 256
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Melting point = 378–379 K
a = 5.8433 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0096 (8) Å	Cell parameters from 945 reflections
c = 13.8089 (13) Å	θ = 2.7–25.4°
α = 74.061 (1)°	µ = 0.09 mm−1
β = 84.589 (1)°	T = 298 K
γ = 87.372 (2)°	Triclinic, colourless
V = 618.54 (11) Å3	0.23 × 0.20 × 0.15 mm

Siemens SMART CCD area-detector diffractometer	2167 independent reflections
Radiation source: fine-focus sealed tube	1291 reflections with I > 2σ(I)
graphite	Rint = 0.026
phi and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.980, Tmax = 0.987	k = −9→9
3169 measured reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
2167 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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	0.6013 (3)	0.8182 (2)	−0.02477 (10)	0.0812 (5)
O2	0.8544 (3)	0.91909 (18)	0.08846 (10)	0.0723 (5)
H2	0.8070	0.9162	0.0349	0.108*
O3	0.6839 (2)	0.71044 (16)	0.44284 (9)	0.0584 (4)
C1	0.2766 (4)	0.6428 (3)	0.03392 (16)	0.0804 (7)
H1A	0.2655	0.6613	−0.0372	0.121*
H1B	0.1382	0.6848	0.0635	0.121*
H1C	0.2971	0.5210	0.0653	0.121*
C2	0.4770 (4)	0.7384 (3)	0.04958 (16)	0.0627 (6)
C3	0.5296 (3)	0.7344 (2)	0.15150 (13)	0.0499 (5)
C4	0.7175 (3)	0.8243 (2)	0.16617 (13)	0.0529 (5)
C5	0.7750 (3)	0.8181 (2)	0.26222 (13)	0.0520 (5)
H5	0.9021	0.8771	0.2705	0.062*
C6	0.6417 (3)	0.7236 (2)	0.34562 (13)	0.0479 (5)
C7	0.4525 (3)	0.6338 (2)	0.33393 (14)	0.0544 (5)
H7	0.3636	0.5700	0.3902	0.065*
C8	0.3993 (3)	0.6409 (2)	0.23848 (14)	0.0566 (5)
H8	0.2719	0.5815	0.2310	0.068*
C9	0.8747 (3)	0.8038 (3)	0.45748 (14)	0.0605 (6)
H9A	0.8578	0.9257	0.4220	0.073*
H9B	1.0162	0.7594	0.4301	0.073*
C10	0.8863 (3)	0.7845 (2)	0.56755 (14)	0.0501 (5)
C11	0.7172 (3)	0.8552 (3)	0.62181 (15)	0.0618 (6)
H11	0.5887	0.9088	0.5905	0.074*
C12	0.7353 (4)	0.8478 (3)	0.72185 (15)	0.0655 (6)
H12	0.6197	0.8961	0.7574	0.079*
C13	0.9239 (4)	0.7690 (3)	0.76880 (16)	0.0654 (6)
H13	0.9373	0.7646	0.8360	0.078*
C14	1.0919 (4)	0.6970 (3)	0.71643 (17)	0.0688 (6)
H14	1.2196	0.6430	0.7482	0.083*
C15	1.0730 (4)	0.7039 (3)	0.61631 (15)	0.0606 (6)
H15	1.1878	0.6535	0.5815	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.1067 (13)	0.0896 (12)	0.0446 (9)	0.0045 (10)	−0.0021 (9)	−0.0160 (8)
O2	0.0836 (10)	0.0796 (11)	0.0449 (8)	−0.0142 (8)	0.0097 (7)	−0.0051 (7)
O3	0.0708 (9)	0.0625 (9)	0.0418 (8)	−0.0226 (7)	−0.0022 (6)	−0.0115 (6)
C1	0.0932 (18)	0.0912 (18)	0.0669 (15)	0.0076 (15)	−0.0257 (13)	−0.0336 (13)
C2	0.0768 (16)	0.0593 (14)	0.0544 (14)	0.0154 (12)	−0.0087 (12)	−0.0211 (11)
C3	0.0601 (13)	0.0478 (12)	0.0422 (12)	0.0036 (10)	−0.0029 (9)	−0.0139 (9)
C4	0.0627 (14)	0.0488 (12)	0.0410 (12)	0.0001 (10)	0.0065 (10)	−0.0057 (9)
C5	0.0569 (13)	0.0515 (12)	0.0464 (12)	−0.0099 (10)	−0.0014 (10)	−0.0106 (9)
C6	0.0593 (12)	0.0441 (11)	0.0385 (11)	−0.0048 (10)	0.0007 (9)	−0.0096 (9)
C7	0.0612 (13)	0.0548 (13)	0.0461 (12)	−0.0141 (10)	0.0056 (10)	−0.0134 (9)
C8	0.0581 (13)	0.0589 (13)	0.0558 (13)	−0.0075 (10)	−0.0035 (10)	−0.0202 (10)
C9	0.0640 (14)	0.0650 (14)	0.0533 (13)	−0.0178 (11)	−0.0017 (10)	−0.0158 (10)
C10	0.0537 (12)	0.0511 (12)	0.0466 (12)	−0.0088 (10)	−0.0041 (10)	−0.0137 (9)
C11	0.0546 (13)	0.0719 (15)	0.0578 (14)	0.0027 (11)	−0.0098 (10)	−0.0147 (11)
C12	0.0641 (14)	0.0770 (16)	0.0577 (14)	−0.0032 (12)	0.0022 (11)	−0.0245 (11)
C13	0.0768 (16)	0.0720 (16)	0.0485 (13)	−0.0132 (13)	−0.0077 (12)	−0.0158 (11)
C14	0.0660 (15)	0.0761 (16)	0.0606 (15)	0.0005 (12)	−0.0168 (12)	−0.0088 (12)
C15	0.0606 (14)	0.0612 (14)	0.0595 (14)	0.0012 (11)	0.0002 (11)	−0.0178 (10)

O1—C2	1.238 (2)	C7—H7	0.9300
O2—C4	1.347 (2)	C8—H8	0.9300
O2—H2	0.8200	C9—C10	1.493 (2)
O3—C6	1.362 (2)	C9—H9A	0.9700
O3—C9	1.430 (2)	C9—H9B	0.9700
C1—C2	1.491 (3)	C10—C15	1.377 (3)
C1—H1A	0.9600	C10—C11	1.379 (3)
C1—H1B	0.9600	C11—C12	1.380 (2)
C1—H1C	0.9600	C11—H11	0.9300
C2—C3	1.460 (3)	C12—C13	1.371 (3)
C3—C4	1.400 (3)	C12—H12	0.9300
C3—C8	1.404 (2)	C13—C14	1.365 (3)
C4—C5	1.386 (2)	C13—H13	0.9300
C5—C6	1.383 (2)	C14—C15	1.383 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.392 (2)	C15—H15	0.9300
C7—C8	1.368 (2)
C4—O2—H2	109.5	C7—C8—H8	118.8
C6—O3—C9	117.04 (14)	C3—C8—H8	118.8
C2—C1—H1A	109.5	O3—C9—C10	109.89 (15)
C2—C1—H1B	109.5	O3—C9—H9A	109.7
H1A—C1—H1B	109.5	C10—C9—H9A	109.7
C2—C1—H1C	109.5	O3—C9—H9B	109.7
H1A—C1—H1C	109.5	C10—C9—H9B	109.7
H1B—C1—H1C	109.5	H9A—C9—H9B	108.2
O1—C2—C3	120.3 (2)	C15—C10—C11	118.14 (18)
O1—C2—C1	119.2 (2)	C15—C10—C9	120.72 (17)
C3—C2—C1	120.5 (2)	C11—C10—C9	121.03 (18)
C4—C3—C8	116.92 (17)	C10—C11—C12	121.11 (19)
C4—C3—C2	120.48 (19)	C10—C11—H11	119.4
C8—C3—C2	122.6 (2)	C12—C11—H11	119.4
O2—C4—C5	116.22 (19)	C13—C12—C11	119.94 (19)
O2—C4—C3	122.26 (17)	C13—C12—H12	120.0
C5—C4—C3	121.51 (17)	C11—C12—H12	120.0
C6—C5—C4	119.41 (19)	C14—C13—C12	119.7 (2)
C6—C5—H5	120.3	C14—C13—H13	120.2
C4—C5—H5	120.3	C12—C13—H13	120.2
O3—C6—C5	123.69 (18)	C13—C14—C15	120.3 (2)
O3—C6—C7	115.64 (16)	C13—C14—H14	119.8
C5—C6—C7	120.67 (17)	C15—C14—H14	119.8
C8—C7—C6	119.02 (18)	C10—C15—C14	120.81 (19)
C8—C7—H7	120.5	C10—C15—H15	119.6
C6—C7—H7	120.5	C14—C15—H15	119.6
C7—C8—C3	122.5 (2)
O1—C2—C3—C4	1.6 (3)	C5—C6—C7—C8	−0.3 (3)
C1—C2—C3—C4	−179.90 (17)	C6—C7—C8—C3	0.5 (3)
O1—C2—C3—C8	−177.70 (18)	C4—C3—C8—C7	−1.0 (3)
C1—C2—C3—C8	0.8 (3)	C2—C3—C8—C7	178.29 (16)
C8—C3—C4—O2	−179.70 (16)	C6—O3—C9—C10	176.25 (14)
C2—C3—C4—O2	1.0 (3)	O3—C9—C10—C15	117.1 (2)
C8—C3—C4—C5	1.3 (3)	O3—C9—C10—C11	−66.5 (2)
C2—C3—C4—C5	−178.00 (16)	C15—C10—C11—C12	0.9 (3)
O2—C4—C5—C6	179.84 (16)	C9—C10—C11—C12	−175.56 (18)
C3—C4—C5—C6	−1.1 (3)	C10—C11—C12—C13	0.0 (3)
C9—O3—C6—C5	1.4 (2)	C11—C12—C13—C14	−0.6 (3)
C9—O3—C6—C7	−178.88 (15)	C12—C13—C14—C15	0.3 (3)
C4—C5—C6—O3	−179.73 (15)	C11—C10—C15—C14	−1.2 (3)
C4—C5—C6—C7	0.6 (3)	C9—C10—C15—C14	175.30 (19)
O3—C6—C7—C8	−179.99 (15)	C13—C14—C15—C10	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.84	2.554 (2)	146
C1—H1B···O2i	0.96	2.52	3.408 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.84	2.554 (2)	146
C1—H1B⋯O2i	0.96	2.52	3.408 (3)	154

Symmetry code: (i) .