Crystal structure of (2S/2R,3S/3R)-3-hydroxy-2-phenyl-chroman-4-one.

In the title mol-ecule, C15H12O3, the C atoms bearing the hy-droxy group and the phenyl ring are disordered over two sets of sites with refined occupancies of 0.573 (7) and 0.427 (7). There is also disorder of the phenyl ring but the hy-droxy group was refined as ordered. The dihedral angles between the benzene ring of the chromane ring system and the phenyl ring are 89.7 (2)° for the major component of disorder and 72.1 (3)° for the minor component. Both disorder components of the the di-hydro-pyran ring are in a half-chair conformation. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) graph-set motif. Weak C-H⋯π inter-actions link these dimers into ladders along [001].

Related literature

For the synthesis and applications of flavone derivatives, see: Gaspar et al. (2014 ▸); Huang et al. (2007 ▸); Yu et al. (2003 ▸); Phosrithong et al. (2012 ▸); Harborne & Williams (2000 ▸); Tanaka & Sugino (2001 ▸); Saxena et al. (1985 ▸). For the synthesis of the title compound, see: Juvale et al. (2013 ▸). For a related structure, see: Piaskowska et al. (2013 ▸).

Experimental

Crystal data

C15H12O3

M = 240.25

Monoclinic,

a = 5.3068 (3) Å

b = 26.7110 (18) Å

c = 9.4679 (6) Å

β = 117.431 (3)°

V = 1191.18 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.16 × 0.11 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▸) T min = 0.615, T max = 0.745

6701 measured reflections

2356 independent reflections

1517 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.148

S = 1.06

2356 reflections

216 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2011 ▸); cell refinement: SAINT (Bruker, 2011 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015001346/lh5747sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001346/lh5747Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015001346/lh5747Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015001346/lh5747fig1.tif

The mol­ecule structure of the title compound. Displacement are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radius. The minor component of disorder is not shown.

Click here for additional data file.

. DOI: 10.1107/S2056989015001346/lh5747fig2.tif

Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines and C—H⋯π intectations as green unbroken lines. The minor component of disorder is not shown.

CCDC reference: 1044756

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12O3	F(000) = 504
Mr = 240.25	Dx = 1.34 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1712 reflections
a = 5.3068 (3) Å	θ = 2.5–23.2°
b = 26.7110 (18) Å	µ = 0.09 mm−1
c = 9.4679 (6) Å	T = 295 K
β = 117.431 (3)°	Prism, colorless
V = 1191.18 (13) Å3	0.16 × 0.11 × 0.08 mm
Z = 4

Bruker APEXII diffractometer	2356 independent reflections
Radiation source: Enraf Nonius FR590	1517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
CCD rotation images, thick slices scans	θmax = 26.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −5→6
Tmin = 0.615, Tmax = 0.745	k = −32→31
6701 measured reflections	l = −11→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.5327P] where P = (Fo2 + 2Fc2)/3
2356 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.14 e Å−3
30 restraints	Δρmin = −0.16 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	Occ. (<1)
O1	0.4498 (4)	0.85751 (6)	0.56442 (18)	0.0538 (5)
O2	0.8643 (5)	0.98972 (7)	0.6185 (2)	0.0768 (6)
O3	0.7507 (5)	0.93216 (8)	0.3576 (2)	0.0811 (7)
C1	0.5095 (5)	0.88656 (9)	0.6949 (3)	0.0487 (6)
C2	0.4263 (6)	0.86841 (11)	0.8046 (3)	0.0654 (8)
H2A	0.3327	0.8379	0.7875	0.079*
C3	0.4833 (7)	0.89589 (12)	0.9380 (3)	0.0782 (9)
H3A	0.428	0.8837	1.0116	0.094*
C4	0.6224 (8)	0.94163 (13)	0.9653 (3)	0.0826 (10)
H4A	0.6623	0.9598	1.057	0.099*
C5	0.7001 (7)	0.95974 (11)	0.8560 (3)	0.0694 (8)
H5A	0.7888	0.9908	0.8725	0.083*
C6	0.6481 (5)	0.93229 (9)	0.7201 (3)	0.0504 (6)
C7	0.7425 (6)	0.95026 (10)	0.6059 (3)	0.0590 (7)
C8	0.7356 (10)	0.91069 (15)	0.4871 (5)	0.0480 (15)	0.573 (7)
H8A	0.8973	0.888	0.5412	0.058*	0.573 (7)
C9	0.4642 (10)	0.88120 (18)	0.4324 (4)	0.0440 (14)	0.573 (7)
H9A	0.3063	0.905	0.386	0.053*	0.573 (7)
C8A	0.6023 (12)	0.9234 (2)	0.4446 (5)	0.048 (2)	0.427 (7)
H8AA	0.4052	0.9346	0.3836	0.058*	0.427 (7)
C9A	0.6092 (14)	0.8684 (2)	0.4818 (8)	0.0491 (18)	0.427 (7)
H9AA	0.8071	0.859	0.5506	0.059*	0.427 (7)
C10	0.4143 (17)	0.8417 (2)	0.3093 (6)	0.0438 (19)	0.573 (7)
C11	0.1560 (16)	0.8427 (3)	0.1717 (8)	0.066 (2)	0.573 (7)
H11A	0.0207	0.8667	0.1596	0.08*	0.573 (7)
C12	0.0997 (14)	0.8077 (3)	0.0521 (6)	0.082 (3)	0.573 (7)
H12A	−0.0731	0.8083	−0.0399	0.099*	0.573 (7)
C13	0.3018 (18)	0.7718 (3)	0.0702 (8)	0.075 (4)	0.573 (7)
H13A	0.2642	0.7484	−0.0098	0.09*	0.573 (7)
C14	0.5602 (16)	0.7708 (3)	0.2078 (9)	0.0589 (19)	0.573 (7)
H14A	0.6954	0.7468	0.2199	0.071*	0.573 (7)
C15	0.6165 (13)	0.8058 (3)	0.3273 (7)	0.0531 (19)	0.573 (7)
H15A	0.7893	0.8052	0.4194	0.064*	0.573 (7)
C10A	0.499 (2)	0.8360 (4)	0.3363 (9)	0.054 (3)	0.427 (7)
C11A	0.212 (2)	0.8324 (3)	0.2302 (10)	0.053 (2)	0.427 (7)
H11B	0.0805	0.8519	0.2447	0.063*	0.427 (7)
C12A	0.1204 (18)	0.7995 (4)	0.1023 (10)	0.063 (3)	0.427 (7)
H12B	−0.0718	0.797	0.0313	0.076*	0.427 (7)
C13A	0.317 (3)	0.7703 (3)	0.0806 (11)	0.063 (5)	0.427 (7)
H13B	0.2555	0.7482	−0.005	0.076*	0.427 (7)
C14A	0.604 (2)	0.7739 (5)	0.1867 (13)	0.081 (4)	0.427 (7)
H14B	0.735	0.7544	0.1721	0.097*	0.427 (7)
C15A	0.6950 (16)	0.8068 (5)	0.3145 (11)	0.066 (3)	0.427 (7)
H15B	0.8872	0.8093	0.3855	0.079*	0.427 (7)
H3O	0.843 (9)	0.9610 (11)	0.382 (5)	0.160 (18)*

	U11	U22	U33	U12	U13	U23
O1	0.0702 (11)	0.0484 (10)	0.0507 (10)	−0.0118 (8)	0.0346 (9)	−0.0009 (7)
O2	0.0990 (16)	0.0637 (12)	0.0829 (14)	−0.0364 (11)	0.0548 (13)	−0.0229 (10)
O3	0.1237 (19)	0.0708 (14)	0.0775 (13)	−0.0378 (13)	0.0709 (14)	−0.0188 (11)
C1	0.0544 (14)	0.0501 (14)	0.0424 (12)	0.0046 (12)	0.0229 (11)	0.0071 (11)
C2	0.085 (2)	0.0643 (17)	0.0572 (16)	0.0026 (15)	0.0411 (16)	0.0131 (13)
C3	0.110 (3)	0.082 (2)	0.0583 (18)	0.0144 (19)	0.0524 (18)	0.0184 (16)
C4	0.124 (3)	0.080 (2)	0.0492 (16)	0.016 (2)	0.0449 (19)	0.0012 (15)
C5	0.092 (2)	0.0647 (18)	0.0500 (15)	−0.0016 (15)	0.0312 (15)	−0.0051 (13)
C6	0.0578 (15)	0.0511 (15)	0.0414 (12)	0.0033 (12)	0.0220 (12)	0.0015 (11)
C7	0.0714 (17)	0.0544 (16)	0.0567 (16)	−0.0152 (14)	0.0340 (14)	−0.0079 (12)
C8	0.046 (3)	0.052 (3)	0.049 (3)	−0.006 (2)	0.024 (2)	0.003 (2)
C9	0.049 (3)	0.045 (3)	0.046 (3)	−0.008 (2)	0.029 (2)	−0.003 (2)
C8A	0.067 (5)	0.040 (4)	0.044 (4)	0.003 (3)	0.030 (4)	0.005 (3)
C9A	0.040 (4)	0.053 (4)	0.053 (4)	−0.001 (3)	0.021 (3)	−0.001 (3)
C10	0.046 (5)	0.046 (4)	0.053 (4)	−0.013 (3)	0.034 (4)	−0.005 (3)
C11	0.050 (3)	0.058 (5)	0.073 (5)	0.002 (3)	0.013 (4)	−0.007 (4)
C12	0.067 (5)	0.085 (6)	0.075 (5)	0.000 (4)	0.016 (4)	−0.021 (4)
C13	0.062 (6)	0.088 (9)	0.080 (8)	−0.031 (5)	0.038 (6)	−0.027 (6)
C14	0.068 (4)	0.044 (4)	0.073 (4)	0.017 (3)	0.040 (4)	0.002 (3)
C15	0.051 (4)	0.061 (4)	0.044 (3)	0.001 (4)	0.018 (3)	0.000 (3)
C10A	0.053 (7)	0.051 (6)	0.061 (5)	−0.012 (4)	0.029 (4)	−0.005 (4)
C11A	0.052 (6)	0.045 (5)	0.067 (7)	0.014 (4)	0.032 (6)	0.002 (4)
C12A	0.052 (5)	0.063 (5)	0.058 (5)	−0.013 (4)	0.011 (4)	−0.014 (5)
C13A	0.101 (11)	0.022 (6)	0.064 (9)	0.011 (6)	0.036 (8)	−0.008 (5)
C14A	0.090 (7)	0.078 (8)	0.084 (8)	−0.001 (6)	0.050 (6)	−0.012 (6)
C15A	0.059 (5)	0.078 (6)	0.076 (5)	−0.002 (5)	0.045 (5)	−0.004 (4)

O1—C1	1.367 (3)	C8A—H8AA	0.98
O1—C9A	1.422 (4)	C9A—C10A	1.498 (4)
O1—C9	1.434 (4)	C9A—H9AA	0.98
O2—C7	1.213 (3)	C10—C11	1.39
O3—C8	1.389 (4)	C10—C15	1.39
O3—C8A	1.396 (4)	C11—C12	1.39
O3—H3O	0.885 (19)	C11—H11A	0.93
C1—C6	1.388 (3)	C12—C13	1.39
C1—C2	1.390 (3)	C12—H12A	0.93
C2—C3	1.369 (4)	C13—C14	1.39
C2—H2A	0.93	C13—H13A	0.93
C3—C4	1.389 (4)	C14—C15	1.39
C3—H3A	0.93	C14—H14A	0.93
C4—C5	1.367 (4)	C15—H15A	0.93
C4—H4A	0.93	C10A—C11A	1.39
C5—C6	1.394 (3)	C10A—C15A	1.39
C5—H5A	0.93	C11A—C12A	1.39
C6—C7	1.466 (3)	C11A—H11B	0.93
C7—C8	1.532 (4)	C12A—C13A	1.39
C7—C8A	1.534 (5)	C12A—H12B	0.93
C8—C9	1.509 (4)	C13A—C14A	1.39
C8—H8A	0.98	C13A—H13B	0.93
C9—C10	1.502 (4)	C14A—C15A	1.39
C9—H9A	0.98	C14A—H14B	0.93
C8A—C9A	1.507 (5)	C15A—H15B	0.93
C1—O1—C9A	115.6 (3)	O3—C8A—H8AA	109.9
C1—O1—C9	117.0 (2)	C9A—C8A—H8AA	109.9
C9A—O1—C9	31.3 (2)	C7—C8A—H8AA	109.9
C8—O3—C8A	29.9 (3)	O1—C9A—C10A	107.9 (5)
C8—O3—H3O	113 (3)	O1—C9A—C8A	111.8 (4)
C8A—O3—H3O	113 (3)	C10A—C9A—C8A	113.0 (6)
O1—C1—C6	122.6 (2)	O1—C9A—H9AA	108
O1—C1—C2	117.1 (2)	C10A—C9A—H9AA	108
C6—C1—C2	120.3 (2)	C8A—C9A—H9AA	108
C3—C2—C1	119.4 (3)	C11—C10—C15	120
C3—C2—H2A	120.3	C11—C10—C9	117.4 (5)
C1—C2—H2A	120.3	C15—C10—C9	122.6 (5)
C2—C3—C4	121.0 (3)	C12—C11—C10	120
C2—C3—H3A	119.5	C12—C11—H11A	120
C4—C3—H3A	119.5	C10—C11—H11A	120
C5—C4—C3	119.4 (3)	C11—C12—C13	120
C5—C4—H4A	120.3	C11—C12—H12A	120
C3—C4—H4A	120.3	C13—C12—H12A	120
C4—C5—C6	120.8 (3)	C14—C13—C12	120
C4—C5—H5A	119.6	C14—C13—H13A	120
C6—C5—H5A	119.6	C12—C13—H13A	120
C1—C6—C5	119.0 (2)	C13—C14—C15	120
C1—C6—C7	119.7 (2)	C13—C14—H14A	120
C5—C6—C7	121.3 (2)	C15—C14—H14A	120
O2—C7—C6	124.0 (2)	C14—C15—C10	120
O2—C7—C8	120.2 (2)	C14—C15—H15A	120
C6—C7—C8	114.5 (2)	C10—C15—H15A	120
O2—C7—C8A	119.7 (3)	C11A—C10A—C15A	120
C6—C7—C8A	114.0 (3)	C11A—C10A—C9A	122.6 (8)
C8—C7—C8A	27.1 (2)	C15A—C10A—C9A	117.3 (8)
O3—C8—C9	110.3 (3)	C12A—C11A—C10A	120
O3—C8—C7	111.8 (3)	C12A—C11A—H11B	120
C9—C8—C7	107.9 (3)	C10A—C11A—H11B	120
O3—C8—H8A	108.9	C11A—C12A—C13A	120
C9—C8—H8A	108.9	C11A—C12A—H12B	120
C7—C8—H8A	108.9	C13A—C12A—H12B	120
O1—C9—C10	107.8 (4)	C12A—C13A—C14A	120
O1—C9—C8	110.9 (3)	C12A—C13A—H13B	120
C10—C9—C8	115.6 (5)	C14A—C13A—H13B	120
O1—C9—H9A	107.4	C15A—C14A—C13A	120
C10—C9—H9A	107.4	C15A—C14A—H14B	120
C8—C9—H9A	107.4	C13A—C14A—H14B	120
O3—C8A—C9A	109.9 (4)	C14A—C15A—C10A	120
O3—C8A—C7	111.2 (3)	C14A—C15A—H15B	120
C9A—C8A—C7	105.9 (4)	C10A—C15A—H15B	120
C9A—O1—C1—C6	18.5 (4)	O2—C7—C8A—O3	32.0 (6)
C9—O1—C1—C6	−16.6 (4)	C6—C7—C8A—O3	−164.2 (3)
C9A—O1—C1—C2	−161.2 (4)	C8—C7—C8A—O3	−67.0 (5)
C9—O1—C1—C2	163.7 (3)	O2—C7—C8A—C9A	151.4 (4)
O1—C1—C2—C3	179.4 (2)	C6—C7—C8A—C9A	−44.8 (5)
C6—C1—C2—C3	−0.3 (4)	C8—C7—C8A—C9A	52.5 (5)
C1—C2—C3—C4	0.1 (5)	C1—O1—C9A—C10A	−175.4 (5)
C2—C3—C4—C5	0.9 (5)	C9—O1—C9A—C10A	−75.0 (9)
C3—C4—C5—C6	−1.7 (5)	C1—O1—C9A—C8A	−50.5 (6)
O1—C1—C6—C5	179.8 (2)	C9—O1—C9A—C8A	49.9 (5)
C2—C1—C6—C5	−0.5 (4)	O3—C8A—C9A—O1	−177.4 (4)
O1—C1—C6—C7	−1.6 (4)	C7—C8A—C9A—O1	62.3 (6)
C2—C1—C6—C7	178.1 (2)	O3—C8A—C9A—C10A	−55.4 (7)
C4—C5—C6—C1	1.5 (4)	C7—C8A—C9A—C10A	−175.7 (5)
C4—C5—C6—C7	−177.1 (3)	O1—C9—C10—C11	107.8 (5)
C1—C6—C7—O2	179.8 (3)	C8—C9—C10—C11	−127.5 (4)
C5—C6—C7—O2	−1.6 (4)	O1—C9—C10—C15	−73.4 (6)
C1—C6—C7—C8	−13.0 (4)	C8—C9—C10—C15	51.3 (6)
C5—C6—C7—C8	165.6 (3)	C15—C10—C11—C12	0
C1—C6—C7—C8A	16.8 (4)	C9—C10—C11—C12	178.8 (6)
C5—C6—C7—C8A	−164.6 (3)	C10—C11—C12—C13	0
C8A—O3—C8—C9	51.2 (5)	C11—C12—C13—C14	0
C8A—O3—C8—C7	−68.9 (4)	C12—C13—C14—C15	0
O2—C7—C8—O3	−28.7 (5)	C13—C14—C15—C10	0
C6—C7—C8—O3	163.6 (3)	C11—C10—C15—C14	0
C8A—C7—C8—O3	68.3 (4)	C9—C10—C15—C14	−178.7 (6)
O2—C7—C8—C9	−150.2 (3)	O1—C9A—C10A—C11A	50.0 (9)
C6—C7—C8—C9	42.1 (4)	C8A—C9A—C10A—C11A	−74.2 (8)
C8A—C7—C8—C9	−53.2 (5)	O1—C9A—C10A—C15A	−126.3 (6)
C1—O1—C9—C10	175.6 (4)	C8A—C9A—C10A—C15A	109.5 (6)
C9A—O1—C9—C10	80.1 (8)	C15A—C10A—C11A—C12A	0
C1—O1—C9—C8	48.1 (5)	C9A—C10A—C11A—C12A	−176.2 (9)
C9A—O1—C9—C8	−47.4 (5)	C10A—C11A—C12A—C13A	0
O3—C8—C9—O1	178.2 (3)	C11A—C12A—C13A—C14A	0
C7—C8—C9—O1	−59.4 (5)	C12A—C13A—C14A—C15A	0
O3—C8—C9—C10	55.1 (5)	C13A—C14A—C15A—C10A	0
C7—C8—C9—C10	177.6 (4)	C11A—C10A—C15A—C14A	0
C8—O3—C8A—C9A	−48.9 (5)	C9A—C10A—C15A—C14A	176.4 (9)
C8—O3—C8A—C7	68.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.89 (4)	2.04 (4)	2.856 (3)	153 (4)
C3—H3A···Cg1ii	0.93	2.74	3.596 (5)	153
C3—H3A···Cg2ii	0.93	2.92	3.756 (5)	151

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C10C15 and C10AC15A rings, respectively.

DHA	DH	HA	D A	DHA
O3H3OO2i	0.89(4)	2.04(4)	2.856(3)	153(4)
C3H3A Cg1ii	0.93	2.74	3.596(5)	153
C3H3A Cg2ii	0.93	2.92	3.756(5)	151

Symmetry codes: (i) ; (ii) .