rac-3-(4-Hy-droxy-benz-yl)chroman-4-one.

In the racemic title compound, C16H14O3, the ring of the 4-hy-droxy-benzyl substituent group forms a dihedral angle of 80.12 (12)° with the benzene ring of the chromanone system. Two C atoms of the pyran-one ring and the H atoms on the benzyl α-C atom are disordered over two sites, with site-occupation factors of 0.818 (8) and 0.182 (8). The crystal structure is stabilized by O-H⋯O hydrogen bonds, which form parallel one-dimensional zigzag chains down the c axis and are inter-connected by both methine C-H⋯O hydrogen bonds and weak aromatic C-H⋯π inter-actions, giving a sheet structure lying parallel to [011].

Related literature

For general background on the properties of isoflavanones (derivatives of 3-benzyl-4H-chromen-4-one), see: Klymchenko et al. (2003 ▶); Sengupta & Kasha (1979 ▶). For related structures, see: Etter et al. (1986 ▶); Waller et al. (2003 ▶); Wera et al. (2011 ▶); Shalini et al. (2013 ▶). For inter­molecular inter­actions, see: Takahashi et al. (2001 ▶). For ring-puckering calculations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H14O3

M = 254.27

Monoclinic,

a = 5.2570 (2) Å

b = 17.0254 (7) Å

c = 14.6879 (5) Å

β = 97.806 (2)°

V = 1302.42 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.962, T max = 0.991

12297 measured reflections

2288 independent reflections

1523 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.11

2288 reflections

187 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014645/zs2259sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014645/zs2259Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014645/zs2259Isup3.cml

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

C16H14O3	F(000) = 536
Mr = 254.27	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3775 reflections
a = 5.2570 (2) Å	θ = 2.5–23.5°
b = 17.0254 (7) Å	µ = 0.09 mm−1
c = 14.6879 (5) Å	T = 293 K
β = 97.806 (2)°	Block, colourless
V = 1302.42 (9) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEX2 CCD diffractometer	2288 independent reflections
Radiation source: fine-focus sealed tube	1523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.962, Tmax = 0.991	k = −17→20
12297 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.4082P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2288 reflections	Δρmax = 0.13 e Å−3
187 parameters	Δρmin = −0.11 e Å−3
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (15)

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	Occ. (<1)
C1	1.4022 (4)	−0.27353 (12)	1.13065 (15)	0.0628 (6)
C2	1.2332 (4)	−0.28490 (13)	1.05275 (15)	0.0717 (6)
H2	1.0932	−0.3182	1.0534	0.086*
C3	1.2717 (5)	−0.24661 (14)	0.97306 (15)	0.0768 (7)
H3	1.1565	−0.2551	0.9201	0.092*
C4	1.4740 (4)	−0.19636 (12)	0.96916 (14)	0.0620 (6)
C5	1.6411 (4)	−0.18607 (13)	1.04841 (16)	0.0685 (6)
H5	1.7807	−0.1526	1.0481	0.082*
C6	1.6067 (4)	−0.22434 (14)	1.12857 (16)	0.0741 (6)
H6	1.7230	−0.2166	1.1814	0.089*
C7	1.5106 (4)	−0.15507 (15)	0.88088 (15)	0.0770 (7)
H7A	1.6694	−0.1253	0.8906	0.092*	0.818 (8)
H7B	1.5272	−0.1942	0.8340	0.092*	0.818 (8)
H7C	1.6938	−0.1473	0.8820	0.092*	0.182 (8)
H7D	1.4570	−0.1915	0.8312	0.092*	0.182 (8)
C8	1.2935 (8)	−0.10032 (19)	0.8465 (2)	0.0608 (9)	0.818 (8)
H8	1.1365	−0.1320	0.8389	0.073*	0.818 (8)
C9	1.2480 (9)	−0.0336 (3)	0.9090 (2)	0.0726 (11)	0.818 (8)
H9A	1.2381	−0.0543	0.9700	0.087*	0.818 (8)
H9B	1.3937	0.0018	0.9135	0.087*	0.818 (8)
C8'	1.387 (3)	−0.0801 (8)	0.8553 (13)	0.0608 (9)	0.182 (8)
H8'	1.5045	−0.0383	0.8803	0.073*	0.182 (8)
C9'	1.146 (3)	−0.0730 (10)	0.8989 (10)	0.058 (4)	0.182 (8)
H9'1	1.1852	−0.0811	0.9646	0.070*	0.182 (8)
H9'2	1.0246	−0.1130	0.8742	0.070*	0.182 (8)
C10	1.0010 (4)	0.03237 (13)	0.79097 (18)	0.0718 (6)
C11	1.1423 (4)	−0.00044 (12)	0.72734 (15)	0.0671 (6)
C12	1.3175 (4)	−0.06544 (13)	0.75340 (15)	0.0662 (6)
C13	1.1050 (6)	0.02833 (16)	0.63788 (18)	0.0956 (8)
H13	1.1988	0.0074	0.5943	0.115*
C14	0.9319 (7)	0.0870 (2)	0.6134 (3)	0.1193 (11)
H14	0.9071	0.1057	0.5534	0.143*
C15	0.7942 (7)	0.11842 (19)	0.6781 (3)	0.1237 (12)
H15	0.6769	0.1584	0.6612	0.148*
C16	0.8271 (5)	0.09181 (16)	0.7663 (2)	0.0994 (9)
H16	0.7333	0.1135	0.8094	0.119*
O1	1.3727 (3)	−0.30821 (10)	1.21218 (10)	0.0888 (6)
H1	1.2435	−0.3357	1.2055	0.107*
O2	1.4570 (3)	−0.09234 (10)	0.70136 (10)	0.0866 (5)
O3	1.0259 (3)	0.00860 (9)	0.88004 (12)	0.0819 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0626 (13)	0.0639 (14)	0.0646 (13)	0.0046 (11)	0.0181 (11)	0.0075 (11)
C2	0.0703 (14)	0.0750 (15)	0.0719 (15)	−0.0148 (11)	0.0176 (12)	0.0028 (12)
C3	0.0750 (15)	0.0922 (17)	0.0625 (14)	−0.0139 (13)	0.0072 (11)	0.0019 (12)
C4	0.0578 (12)	0.0648 (14)	0.0667 (14)	0.0074 (10)	0.0207 (11)	0.0064 (11)
C5	0.0550 (12)	0.0682 (15)	0.0841 (16)	−0.0017 (10)	0.0156 (11)	0.0113 (12)
C6	0.0676 (14)	0.0841 (17)	0.0685 (14)	−0.0034 (12)	0.0015 (11)	0.0076 (12)
C7	0.0683 (14)	0.0928 (17)	0.0747 (15)	0.0110 (13)	0.0278 (12)	0.0168 (13)
C8	0.074 (2)	0.0546 (17)	0.0585 (15)	−0.0042 (14)	0.0242 (17)	−0.0011 (14)
C9	0.079 (3)	0.080 (3)	0.0608 (18)	0.007 (2)	0.0166 (17)	−0.0059 (18)
C8'	0.074 (2)	0.0546 (17)	0.0585 (15)	−0.0042 (14)	0.0242 (17)	−0.0011 (14)
C9'	0.061 (8)	0.054 (10)	0.065 (8)	−0.009 (6)	0.022 (7)	−0.008 (7)
C10	0.0660 (14)	0.0589 (14)	0.0909 (18)	−0.0062 (11)	0.0119 (13)	−0.0013 (13)
C11	0.0734 (14)	0.0571 (13)	0.0708 (15)	−0.0064 (11)	0.0097 (11)	0.0041 (11)
C12	0.0796 (15)	0.0618 (14)	0.0610 (13)	−0.0042 (11)	0.0229 (12)	−0.0044 (11)
C13	0.118 (2)	0.0855 (19)	0.0816 (18)	−0.0047 (17)	0.0078 (15)	0.0140 (15)
C14	0.134 (3)	0.096 (2)	0.119 (3)	−0.002 (2)	−0.017 (2)	0.036 (2)
C15	0.108 (3)	0.080 (2)	0.173 (4)	0.0091 (18)	−0.016 (3)	0.024 (2)
C16	0.0839 (19)	0.0734 (18)	0.140 (3)	0.0107 (15)	0.0117 (18)	0.0041 (18)
O1	0.0925 (12)	0.1042 (13)	0.0711 (10)	−0.0090 (9)	0.0164 (9)	0.0248 (9)
O2	0.1092 (13)	0.0882 (12)	0.0706 (10)	0.0128 (10)	0.0413 (9)	0.0031 (9)
O3	0.0861 (12)	0.0782 (11)	0.0868 (12)	0.0134 (9)	0.0308 (9)	−0.0065 (9)

C1—O1	1.363 (2)	C9—H9A	0.9700
C1—C2	1.364 (3)	C9—H9B	0.9700
C1—C6	1.366 (3)	C8'—C9'	1.501 (10)
C2—C3	1.379 (3)	C8'—C12	1.513 (18)
C2—H2	0.9300	C8'—H8'	0.9800
C3—C4	1.372 (3)	C9'—O3	1.535 (15)
C3—H3	0.9300	C9'—H9'1	0.9700
C4—C5	1.371 (3)	C9'—H9'2	0.9700
C4—C7	1.510 (3)	C10—O3	1.359 (3)
C5—C6	1.379 (3)	C10—C16	1.379 (3)
C5—H5	0.9300	C10—C11	1.388 (3)
C6—H6	0.9300	C11—C13	1.391 (3)
C7—C8'	1.457 (9)	C11—C12	1.457 (3)
C7—C8	1.507 (4)	C12—O2	1.218 (2)
C7—H7A	0.9700	C13—C14	1.366 (4)
C7—H7B	0.9700	C13—H13	0.9300
C7—H7C	0.9700	C14—C15	1.378 (4)
C7—H7D	0.9700	C14—H14	0.9300
C8—C9	1.500 (4)	C15—C16	1.361 (4)
C8—C12	1.512 (4)	C15—H15	0.9300
C8—H8	0.9800	C16—H16	0.9300
C9—O3	1.388 (4)	O1—H1	0.8200
O1—C1—C2	122.4 (2)	O3—C9—H9A	108.8
O1—C1—C6	118.0 (2)	C8—C9—H9A	108.8
C2—C1—C6	119.6 (2)	O3—C9—H9B	108.8
C1—C2—C3	119.4 (2)	C8—C9—H9B	108.8
C1—C2—H2	120.3	H9A—C9—H9B	107.7
C3—C2—H2	120.3	C7—C8'—C9'	109.5 (10)
C4—C3—C2	122.3 (2)	C7—C8'—C12	116.1 (11)
C4—C3—H3	118.8	C9'—C8'—C12	107.6 (12)
C2—C3—H3	118.8	C7—C8'—H8'	107.8
C5—C4—C3	117.1 (2)	C9'—C8'—H8'	107.8
C5—C4—C7	121.8 (2)	C12—C8'—H8'	107.8
C3—C4—C7	121.1 (2)	C8'—C9'—O3	110.4 (10)
C4—C5—C6	121.4 (2)	C8'—C9'—H9'1	109.6
C4—C5—H5	119.3	O3—C9'—H9'1	109.6
C6—C5—H5	119.3	C8'—C9'—H9'2	109.6
C1—C6—C5	120.2 (2)	O3—C9'—H9'2	109.6
C1—C6—H6	119.9	H9'1—C9'—H9'2	108.1
C5—C6—H6	119.9	O3—C10—C16	116.5 (2)
C8'—C7—C4	121.6 (6)	O3—C10—C11	122.6 (2)
C8—C7—C4	113.3 (2)	C16—C10—C11	121.0 (3)
C8'—C7—H7A	85.7	C10—C11—C13	118.3 (2)
C8—C7—H7A	108.9	C10—C11—C12	120.4 (2)
C4—C7—H7A	108.9	C13—C11—C12	121.2 (2)
C8'—C7—H7B	119.9	O2—C12—C11	122.2 (2)
C8—C7—H7B	108.9	O2—C12—C8	123.4 (2)
C4—C7—H7B	108.9	C11—C12—C8	114.1 (2)
H7A—C7—H7B	107.7	O2—C12—C8'	118.2 (4)
C8'—C7—H7C	106.9	C11—C12—C8'	116.4 (4)
C8—C7—H7C	128.8	C14—C13—C11	120.6 (3)
C4—C7—H7C	106.9	C14—C13—H13	119.7
H7B—C7—H7C	85.5	C11—C13—H13	119.7
C8'—C7—H7D	107.0	C13—C14—C15	119.8 (3)
C8—C7—H7D	90.8	C13—C14—H14	120.1
C4—C7—H7D	106.9	C15—C14—H14	120.1
H7A—C7—H7D	126.9	C16—C15—C14	121.1 (3)
H7C—C7—H7D	106.7	C16—C15—H15	119.5
C9—C8—C7	116.1 (3)	C14—C15—H15	119.5
C9—C8—C12	107.2 (3)	C15—C16—C10	119.3 (3)
C7—C8—C12	113.2 (3)	C15—C16—H16	120.4
C9—C8—H8	106.6	C10—C16—H16	120.4
C7—C8—H8	106.6	C1—O1—H1	109.5
C12—C8—H8	106.6	C10—O3—C9	114.6 (2)
O3—C9—C8	113.7 (3)	C10—O3—C9'	115.2 (5)
O1—C1—C2—C3	178.6 (2)	C10—C11—C12—C8	9.9 (3)
C6—C1—C2—C3	0.1 (3)	C13—C11—C12—C8	−167.7 (3)
C1—C2—C3—C4	−0.7 (4)	C10—C11—C12—C8'	−15.4 (8)
C2—C3—C4—C5	0.7 (3)	C13—C11—C12—C8'	167.0 (7)
C2—C3—C4—C7	−179.8 (2)	C9—C8—C12—O2	146.6 (3)
C3—C4—C5—C6	−0.2 (3)	C7—C8—C12—O2	17.2 (4)
C7—C4—C5—C6	−179.7 (2)	C9—C8—C12—C11	−38.5 (5)
O1—C1—C6—C5	−178.2 (2)	C7—C8—C12—C11	−167.8 (2)
C2—C1—C6—C5	0.4 (3)	C9—C8—C12—C8'	62.8 (11)
C4—C5—C6—C1	−0.3 (3)	C7—C8—C12—C8'	−66.6 (12)
C5—C4—C7—C8'	−93.3 (10)	C7—C8'—C12—O2	−33.5 (13)
C3—C4—C7—C8'	87.3 (10)	C9'—C8'—C12—O2	−156.6 (10)
C5—C4—C7—C8	−117.9 (3)	C7—C8'—C12—C11	165.9 (7)
C3—C4—C7—C8	62.7 (3)	C9'—C8'—C12—C11	42.9 (16)
C8'—C7—C8—C9	−55.0 (17)	C7—C8'—C12—C8	76.2 (15)
C4—C7—C8—C9	61.2 (5)	C9'—C8'—C12—C8	−46.8 (12)
C8'—C7—C8—C12	69.6 (19)	C10—C11—C13—C14	−0.5 (4)
C4—C7—C8—C12	−174.1 (2)	C12—C11—C13—C14	177.1 (2)
C7—C8—C9—O3	−171.8 (2)	C11—C13—C14—C15	0.5 (5)
C12—C8—C9—O3	60.6 (6)	C13—C14—C15—C16	−0.2 (5)
C8—C7—C8'—C9'	48.6 (12)	C14—C15—C16—C10	−0.1 (5)
C4—C7—C8'—C9'	−27 (2)	O3—C10—C16—C15	179.7 (3)
C8—C7—C8'—C12	−73 (2)	C11—C10—C16—C15	0.0 (4)
C4—C7—C8'—C12	−148.8 (6)	C16—C10—O3—C9	−162.3 (3)
C7—C8'—C9'—O3	174.9 (10)	C11—C10—O3—C9	17.4 (4)
C12—C8'—C9'—O3	−58.1 (18)	C16—C10—O3—C9'	160.5 (7)
O3—C10—C11—C13	−179.4 (2)	C11—C10—O3—C9'	−19.8 (7)
C16—C10—C11—C13	0.3 (3)	C8—C9—O3—C10	−50.6 (5)
O3—C10—C11—C12	2.9 (3)	C8—C9—O3—C9'	48.5 (9)
C16—C10—C11—C12	−177.4 (2)	C8'—C9'—O3—C10	48.9 (17)
C10—C11—C12—O2	−175.1 (2)	C8'—C9'—O3—C9	−48.2 (12)
C13—C11—C12—O2	7.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.94	2.752 (2)	173
C8—H8···O1ii	0.98	2.39	3.166 (4)	136
C16—H16···Cg1iii	0.93	3.14	4.022 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.94	2.752 (2)	173
C8—H8⋯O1ii	0.98	2.39	3.166 (4)	136
C16—H16⋯Cg1iii	0.93	3.14	4.022 (3)	159

Symmetry codes: (i) ; (ii) ; (iii) .