2-(4-Hy-droxy-phen-yl)-3-meth-oxy-4H-chromen-4-one.

In the title compound, C16H12O4, the substituent benzene ring and meth-oxy group are twisted relative to the 4H-chromene skeleton by 24.1 (1) and 61.3 (1)°, respectively. In the crystal, mol-ecules are connected by classical O-H⋯O and weak C-H⋯O hydrogen bonds, forming chains parallel to [201]. The 4H-chromene ring systems of adjacent mol-ecules are either parallel or inclined at an angle of 28.9 (1)°.

Related literature

For general features of flavones and flavonols (derivatives of 3-hy­droxy-2-phenyl-4H-chromen-4-one), see: Demchenko (2009 ▶); Ma et al. (2012 ▶). For related structures, see: Wera et al. (2011a ▶,b ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Etter et al. (1990 ▶); Novoa et al. (2006 ▶). For the synthesis, see: Bader et al. (2003 ▶); Wera et al. (2011b ▶).

Experimental

Crystal data

C16H12O4

M = 268.26

Monoclinic,

a = 8.7191 (5) Å

b = 8.8978 (4) Å

c = 16.706 (1) Å

β = 103.801 (6)°

V = 1258.65 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.6 × 0.45 × 0.25 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.943, T max = 0.970

5100 measured reflections

2245 independent reflections

1801 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.03

2245 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010982/xu5696sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010982/xu5696Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010982/xu5696Isup3.cml

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

C16H12O4	F(000) = 560
Mr = 268.26	Dx = 1.416 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 2245 reflections
a = 8.7191 (5) Å	θ = 3.3–25.1°
b = 8.8978 (4) Å	µ = 0.10 mm−1
c = 16.706 (1) Å	T = 295 K
β = 103.801 (6)°	Prism, pale yellow
V = 1258.65 (12) Å3	0.6 × 0.45 × 0.25 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2245 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1801 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.3°
ω scans	h = −7→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −10→10
Tmin = 0.943, Tmax = 0.970	l = −18→19
5100 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1866P] where P = (Fo2 + 2Fc2)/3
2245 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 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	0.26225 (13)	0.08174 (12)	0.03249 (6)	0.0445 (3)
C2	0.31549 (18)	−0.06240 (17)	0.03302 (10)	0.0390 (4)
C3	0.2506 (2)	−0.15818 (18)	−0.02953 (10)	0.0443 (4)
C4	0.1209 (2)	−0.1136 (2)	−0.09642 (10)	0.0503 (5)
C5	−0.0405 (2)	0.1077 (3)	−0.16006 (12)	0.0656 (6)
H5	−0.0915	0.0491	−0.2046	0.079*
C6	−0.0777 (3)	0.2560 (3)	−0.15735 (13)	0.0762 (7)
H6	−0.1540	0.2979	−0.2001	0.091*
C7	−0.0028 (3)	0.3448 (3)	−0.09160 (13)	0.0729 (6)
H7	−0.0295	0.4459	−0.0906	0.087*
C8	0.1101 (2)	0.2854 (2)	−0.02795 (11)	0.0589 (5)
H8	0.1607	0.3449	0.0163	0.071*
C9	0.07400 (19)	0.0433 (2)	−0.09613 (10)	0.0488 (5)
C10	0.14684 (19)	0.1346 (2)	−0.03126 (10)	0.0451 (4)
O11	0.29961 (17)	−0.30466 (13)	−0.02436 (8)	0.0603 (4)
O12	0.05411 (16)	−0.20337 (16)	−0.15021 (8)	0.0712 (4)
C13	0.43909 (17)	−0.09082 (16)	0.10765 (9)	0.0358 (4)
C14	0.4500 (2)	0.00252 (18)	0.17590 (10)	0.0460 (4)
H14	0.3772	0.0799	0.1733	0.055*
C15	0.5654 (2)	−0.01740 (19)	0.24656 (10)	0.0483 (4)
H15	0.5694	0.0456	0.2914	0.058*
C16	0.67592 (19)	−0.12985 (17)	0.25180 (10)	0.0403 (4)
C17	0.66761 (19)	−0.22373 (17)	0.18547 (10)	0.0417 (4)
H17	0.7414	−0.3003	0.1885	0.050*
C18	0.55044 (19)	−0.20481 (16)	0.11453 (10)	0.0406 (4)
H18	0.5458	−0.2697	0.0704	0.049*
C19	0.3675 (3)	−0.3531 (2)	−0.09013 (14)	0.0818 (7)
H19A	0.2869	−0.3571	−0.1405	0.123*
H19B	0.4130	−0.4511	−0.0778	0.123*
H19C	0.4481	−0.2835	−0.0962	0.123*
O20	0.78716 (16)	−0.14223 (15)	0.32342 (8)	0.0600 (4)
H20	0.867 (3)	−0.209 (3)	0.3198 (15)	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0465 (7)	0.0475 (7)	0.0342 (6)	0.0080 (5)	−0.0007 (5)	−0.0006 (5)
C2	0.0394 (9)	0.0405 (9)	0.0364 (9)	−0.0031 (7)	0.0078 (7)	−0.0004 (7)
C3	0.0477 (10)	0.0457 (9)	0.0382 (10)	−0.0106 (8)	0.0074 (8)	−0.0029 (7)
C4	0.0425 (10)	0.0709 (12)	0.0363 (10)	−0.0205 (9)	0.0075 (8)	−0.0040 (8)
C5	0.0418 (10)	0.1093 (18)	0.0412 (11)	−0.0004 (11)	0.0011 (9)	0.0086 (11)
C6	0.0557 (13)	0.123 (2)	0.0467 (13)	0.0313 (13)	0.0047 (10)	0.0234 (13)
C7	0.0751 (14)	0.0945 (16)	0.0489 (13)	0.0405 (13)	0.0144 (11)	0.0157 (11)
C8	0.0638 (12)	0.0716 (13)	0.0405 (11)	0.0243 (10)	0.0109 (9)	0.0053 (9)
C9	0.0357 (9)	0.0756 (12)	0.0339 (9)	−0.0045 (8)	0.0062 (7)	0.0050 (8)
C10	0.0365 (9)	0.0655 (11)	0.0325 (9)	0.0077 (8)	0.0069 (7)	0.0073 (8)
O11	0.0815 (10)	0.0453 (7)	0.0497 (8)	−0.0114 (6)	0.0069 (7)	−0.0083 (6)
O12	0.0654 (9)	0.0919 (10)	0.0484 (8)	−0.0313 (8)	−0.0021 (7)	−0.0173 (7)
C13	0.0363 (8)	0.0346 (8)	0.0356 (9)	−0.0031 (7)	0.0068 (7)	−0.0008 (6)
C14	0.0451 (9)	0.0458 (9)	0.0427 (10)	0.0103 (8)	0.0018 (8)	−0.0065 (7)
C15	0.0497 (10)	0.0511 (10)	0.0389 (10)	0.0079 (8)	−0.0001 (8)	−0.0113 (8)
C16	0.0391 (9)	0.0412 (8)	0.0371 (9)	−0.0008 (7)	0.0020 (7)	0.0038 (7)
C17	0.0413 (9)	0.0362 (8)	0.0471 (10)	0.0060 (7)	0.0092 (8)	0.0029 (7)
C18	0.0458 (10)	0.0370 (8)	0.0387 (9)	−0.0021 (7)	0.0097 (8)	−0.0056 (7)
C19	0.1109 (19)	0.0646 (13)	0.0691 (15)	0.0072 (13)	0.0199 (14)	−0.0224 (11)
O20	0.0549 (8)	0.0682 (9)	0.0459 (8)	0.0154 (6)	−0.0100 (6)	−0.0035 (6)

O1—C10	1.3627 (18)	C9—C10	1.382 (2)
O1—C2	1.3633 (19)	O11—C19	1.433 (3)
C2—C3	1.362 (2)	C13—C18	1.390 (2)
C2—C13	1.462 (2)	C13—C14	1.395 (2)
C3—O11	1.368 (2)	C14—C15	1.368 (2)
C3—C4	1.443 (2)	C14—H14	0.9300
C4—O12	1.239 (2)	C15—C16	1.377 (2)
C4—C9	1.455 (3)	C15—H15	0.9300
C5—C6	1.362 (3)	C16—O20	1.3530 (19)
C5—C9	1.399 (2)	C16—C17	1.376 (2)
C5—H5	0.9300	C17—C18	1.378 (2)
C6—C7	1.384 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.371 (3)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C10	1.383 (3)	C19—H19C	0.9600
C8—H8	0.9300	O20—H20	0.93 (3)
C10—O1—C2	121.13 (13)	C9—C10—C8	122.28 (16)
C3—C2—O1	120.33 (14)	C3—O11—C19	114.71 (15)
C3—C2—C13	129.24 (15)	C18—C13—C14	117.18 (14)
O1—C2—C13	110.41 (12)	C18—C13—C2	123.70 (14)
C2—C3—O11	118.76 (15)	C14—C13—C2	119.10 (14)
C2—C3—C4	121.84 (16)	C15—C14—C13	121.37 (15)
O11—C3—C4	119.09 (14)	C15—C14—H14	119.3
O12—C4—C3	122.05 (18)	C13—C14—H14	119.3
O12—C4—C9	122.48 (17)	C14—C15—C16	120.58 (15)
C3—C4—C9	115.47 (15)	C14—C15—H15	119.7
C6—C5—C9	120.2 (2)	C16—C15—H15	119.7
C6—C5—H5	119.9	O20—C16—C17	123.49 (15)
C9—C5—H5	119.9	O20—C16—C15	117.29 (15)
C5—C6—C7	120.58 (19)	C17—C16—C15	119.22 (15)
C5—C6—H6	119.7	C16—C17—C18	120.29 (14)
C7—C6—H6	119.7	C16—C17—H17	119.9
C8—C7—C6	120.7 (2)	C18—C17—H17	119.9
C8—C7—H7	119.6	C17—C18—C13	121.35 (14)
C6—C7—H7	119.6	C17—C18—H18	119.3
C7—C8—C10	118.22 (19)	C13—C18—H18	119.3
C7—C8—H8	120.9	O11—C19—H19A	109.5
C10—C8—H8	120.9	O11—C19—H19B	109.5
C10—C9—C5	117.95 (18)	H19A—C19—H19B	109.5
C10—C9—C4	119.33 (15)	O11—C19—H19C	109.5
C5—C9—C4	122.71 (17)	H19A—C19—H19C	109.5
O1—C10—C9	121.69 (16)	H19B—C19—H19C	109.5
O1—C10—C8	116.01 (15)	C16—O20—H20	112.6 (15)
C10—O1—C2—C3	−1.9 (2)	C4—C9—C10—O1	0.3 (2)
C10—O1—C2—C13	179.79 (13)	C5—C9—C10—C8	0.0 (3)
O1—C2—C3—O11	−175.76 (14)	C4—C9—C10—C8	178.69 (17)
C13—C2—C3—O11	2.2 (3)	C7—C8—C10—O1	178.60 (17)
O1—C2—C3—C4	−2.3 (2)	C7—C8—C10—C9	0.1 (3)
C13—C2—C3—C4	175.66 (15)	C2—C3—O11—C19	−120.39 (19)
C2—C3—C4—O12	−174.71 (16)	C4—C3—O11—C19	65.9 (2)
O11—C3—C4—O12	−1.2 (3)	C3—C2—C13—C18	23.8 (3)
C2—C3—C4—C9	5.1 (2)	O1—C2—C13—C18	−158.16 (14)
O11—C3—C4—C9	178.60 (15)	C3—C2—C13—C14	−157.69 (17)
C9—C5—C6—C7	0.1 (3)	O1—C2—C13—C14	20.4 (2)
C5—C6—C7—C8	0.0 (3)	C18—C13—C14—C15	0.0 (2)
C6—C7—C8—C10	−0.1 (3)	C2—C13—C14—C15	−178.62 (15)
C6—C5—C9—C10	−0.1 (3)	C13—C14—C15—C16	0.8 (3)
C6—C5—C9—C4	−178.73 (19)	C14—C15—C16—O20	179.61 (16)
O12—C4—C9—C10	175.76 (16)	C14—C15—C16—C17	−0.9 (3)
C3—C4—C9—C10	−4.1 (2)	O20—C16—C17—C18	179.71 (15)
O12—C4—C9—C5	−5.6 (3)	C15—C16—C17—C18	0.3 (2)
C3—C4—C9—C5	174.56 (16)	C16—C17—C18—C13	0.5 (2)
C2—O1—C10—C9	2.9 (2)	C14—C13—C18—C17	−0.7 (2)
C2—O1—C10—C8	−175.60 (15)	C2—C13—C18—C17	177.91 (14)
C5—C9—C10—O1	−178.42 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···O12i	0.93 (3)	1.77 (3)	2.648 (2)	157 (2)
C7—H7···O20ii	0.93	2.56	3.337 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20⋯O12i	0.93 (3)	1.77 (3)	2.648 (2)	157 (2)
C7—H7⋯O20ii	0.93	2.56	3.337 (3)	141

Symmetry codes: (i) ; (ii) .