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

In the title compound, C(16)H(12)O(4), the benzene ring is twisted at an angle of 12.3 (1)° relative to the 4H-chromene skeleton, and an intramolecular O-H⋯O hydrogen bond occurs. The meth-oxy group is almost coplanar with the benzene ring [1.5 (1)°]. In the crystal, inversely oriented mol-ecules are arranged in double (A, A') columns, along the b axis, and are linked by a network of inter-molecular O-H⋯O hydrogen bonds (between A and A') and C-H⋯π contacts (within A or A'). The 4H-chromene cores are parallel within A or A', but make a dihedral angle of 88.6 (1)° between A and A'.

Related literature

For general features of flavonols (derivatives of 3-hy­droxy-2-phenyl-4H-chromen-4-one), see: Demchenko (2009 ▶); Klymchenko et al. (2003 ▶); Sengupta & Kasha (1979 ▶). For related structures, see: Etter et al. (1986 ▶); Waller et al. (2003 ▶); Wera et al. (2011 ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sobottka et al. (2000 ▶).

Experimental

Crystal data

C16H12O4

M = 268.26

Monoclinic,

a = 11.2400 (5) Å

b = 4.9860 (2) Å

c = 21.9907 (9) Å

β = 95.116 (4)°

V = 1227.51 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.87 mm−1

T = 295 K

0.4 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.723, T max = 0.888

7763 measured reflections

2209 independent reflections

1691 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.04

2209 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100167X/om2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100167X/om2398Isup2.hkl

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

C16H12O4	F(000) = 560
Mr = 268.26	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2209 reflections
a = 11.2400 (5) Å	θ = 4.0–68.3°
b = 4.9860 (2) Å	µ = 0.87 mm−1
c = 21.9907 (9) Å	T = 295 K
β = 95.116 (4)°	Needle, colorless
V = 1227.51 (9) Å3	0.4 × 0.05 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2209 independent reflections
Radiation source: Ultra (Cu) X-ray Source'	1691 reflections with I > 2σ(I)
mirror	Rint = 0.031
Detector resolution: 10.4002 pixels mm-1	θmax = 68.3°, θmin = 4.0°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −5→5
Tmin = 0.723, Tmax = 0.888	l = −25→26
7763 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) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.056P)2 + 0.2165P] where P = (Fo2 + 2Fc2)/3
2209 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 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	0.31792 (10)	0.8649 (2)	0.40435 (5)	0.0418 (3)
C2	0.22283 (14)	0.6906 (3)	0.40261 (7)	0.0360 (4)
C3	0.14034 (15)	0.6880 (3)	0.35333 (7)	0.0382 (4)
C4	0.15007 (15)	0.8610 (3)	0.30130 (7)	0.0387 (4)
C5	0.27235 (18)	1.2220 (4)	0.25831 (8)	0.0481 (5)
H5	0.2193	1.2302	0.2234	0.058*
C6	0.37020 (19)	1.3850 (4)	0.26374 (9)	0.0526 (5)
H6	0.3833	1.5046	0.2326	0.063*
C7	0.45087 (18)	1.3732 (4)	0.31592 (9)	0.0510 (5)
H7	0.5176	1.4843	0.3191	0.061*
C8	0.43220 (16)	1.1982 (4)	0.36261 (8)	0.0459 (4)
H8	0.4857	1.1900	0.3973	0.055*
C9	0.25145 (15)	1.0416 (3)	0.30532 (7)	0.0385 (4)
C10	0.33197 (15)	1.0345 (3)	0.35681 (7)	0.0391 (4)
O11	0.04691 (11)	0.5154 (3)	0.35012 (5)	0.0495 (3)
H11	0.012 (2)	0.521 (5)	0.3111 (11)	0.074*
O12	0.07565 (12)	0.8432 (3)	0.25643 (5)	0.0523 (4)
C13	0.22946 (15)	0.5200 (3)	0.45717 (7)	0.0366 (4)
C14	0.33350 (16)	0.5131 (4)	0.49652 (8)	0.0458 (4)
H14	0.3973	0.6231	0.4888	0.055*
C15	0.34395 (16)	0.3468 (4)	0.54671 (8)	0.0485 (5)
H15	0.4151	0.3426	0.5718	0.058*
C16	0.24935 (16)	0.1858 (4)	0.56016 (7)	0.0411 (4)
C17	0.14504 (16)	0.1926 (4)	0.52235 (8)	0.0494 (5)
H17	0.0806	0.0867	0.5311	0.059*
C18	0.13582 (16)	0.3565 (4)	0.47141 (8)	0.0479 (5)
H18	0.0651	0.3573	0.4460	0.057*
O19	0.26808 (12)	0.0309 (3)	0.61117 (5)	0.0532 (4)
C20	0.17391 (19)	−0.1423 (4)	0.62537 (9)	0.0568 (5)
H20A	0.1990	−0.2448	0.6612	0.085*
H20B	0.1541	−0.2616	0.5917	0.085*
H20C	0.1051	−0.0374	0.6328	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0424 (6)	0.0461 (7)	0.0357 (6)	−0.0079 (5)	−0.0038 (5)	0.0054 (5)
C2	0.0354 (8)	0.0395 (9)	0.0327 (8)	−0.0025 (7)	0.0005 (6)	−0.0004 (7)
C3	0.0389 (9)	0.0418 (9)	0.0333 (8)	−0.0001 (7)	−0.0004 (7)	−0.0013 (7)
C4	0.0432 (9)	0.0391 (9)	0.0332 (8)	0.0070 (7)	−0.0005 (7)	−0.0010 (7)
C5	0.0617 (12)	0.0450 (10)	0.0375 (9)	0.0048 (9)	0.0042 (8)	0.0035 (7)
C6	0.0662 (12)	0.0469 (11)	0.0465 (10)	0.0011 (9)	0.0142 (9)	0.0090 (8)
C7	0.0536 (11)	0.0467 (10)	0.0542 (11)	−0.0053 (9)	0.0139 (9)	0.0017 (8)
C8	0.0460 (10)	0.0448 (10)	0.0467 (10)	−0.0030 (8)	0.0037 (8)	0.0009 (8)
C9	0.0449 (9)	0.0361 (9)	0.0347 (8)	0.0063 (7)	0.0046 (7)	−0.0004 (7)
C10	0.0456 (9)	0.0370 (9)	0.0352 (8)	0.0015 (7)	0.0059 (7)	0.0020 (7)
O11	0.0479 (7)	0.0638 (8)	0.0342 (6)	−0.0158 (6)	−0.0108 (5)	0.0056 (6)
O12	0.0593 (8)	0.0566 (8)	0.0376 (7)	0.0003 (6)	−0.0140 (6)	0.0054 (6)
C13	0.0378 (8)	0.0407 (9)	0.0307 (8)	−0.0016 (7)	0.0001 (6)	−0.0009 (7)
C14	0.0400 (9)	0.0572 (11)	0.0391 (9)	−0.0129 (8)	−0.0032 (7)	0.0069 (8)
C15	0.0401 (9)	0.0629 (12)	0.0401 (9)	−0.0094 (9)	−0.0101 (7)	0.0102 (8)
C16	0.0475 (10)	0.0455 (9)	0.0296 (8)	−0.0040 (8)	−0.0013 (7)	0.0019 (7)
C17	0.0444 (10)	0.0587 (11)	0.0438 (10)	−0.0160 (9)	−0.0037 (8)	0.0076 (8)
C18	0.0387 (9)	0.0626 (12)	0.0401 (9)	−0.0094 (9)	−0.0093 (7)	0.0091 (8)
O19	0.0547 (8)	0.0630 (8)	0.0397 (7)	−0.0141 (6)	−0.0076 (6)	0.0156 (6)
C20	0.0661 (13)	0.0593 (12)	0.0447 (10)	−0.0167 (10)	0.0025 (9)	0.0116 (9)

O1—C10	1.3645 (19)	C9—C10	1.386 (2)
O1—C2	1.3755 (19)	O11—H11	0.91 (3)
C2—C3	1.362 (2)	C13—C18	1.389 (2)
C2—C13	1.467 (2)	C13—C14	1.392 (2)
C3—O11	1.355 (2)	C14—C15	1.377 (2)
C3—C4	1.445 (2)	C14—H14	0.9300
C4—O12	1.238 (2)	C15—C16	1.385 (2)
C4—C9	1.449 (2)	C15—H15	0.9300
C5—C6	1.364 (3)	C16—O19	1.363 (2)
C5—C9	1.406 (2)	C16—C17	1.376 (2)
C5—H5	0.9300	C17—C18	1.383 (2)
C6—C7	1.399 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.378 (3)	O19—C20	1.422 (2)
C7—H7	0.9300	C20—H20A	0.9600
C8—C10	1.388 (2)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C10—O1—C2	120.85 (13)	C9—C10—C8	121.70 (16)
C3—C2—O1	120.02 (14)	C3—O11—H11	107.3 (15)
C3—C2—C13	128.80 (15)	C18—C13—C14	117.19 (15)
O1—C2—C13	111.15 (13)	C18—C13—C2	122.71 (14)
O11—C3—C2	121.13 (15)	C14—C13—C2	120.09 (15)
O11—C3—C4	116.80 (14)	C15—C14—C13	121.33 (16)
C2—C3—C4	122.03 (15)	C15—C14—H14	119.3
O12—C4—C3	119.67 (16)	C13—C14—H14	119.3
O12—C4—C9	124.37 (15)	C14—C15—C16	120.53 (16)
C3—C4—C9	115.93 (14)	C14—C15—H15	119.7
C6—C5—C9	120.20 (17)	C16—C15—H15	119.7
C6—C5—H5	119.9	O19—C16—C17	124.91 (16)
C9—C5—H5	119.9	O19—C16—C15	116.04 (15)
C5—C6—C7	120.35 (17)	C17—C16—C15	119.04 (16)
C5—C6—H6	119.8	C16—C17—C18	120.16 (17)
C7—C6—H6	119.8	C16—C17—H17	119.9
C8—C7—C6	120.48 (18)	C18—C17—H17	119.9
C8—C7—H7	119.8	C17—C18—C13	121.73 (16)
C6—C7—H7	119.8	C17—C18—H18	119.1
C7—C8—C10	118.72 (18)	C13—C18—H18	119.1
C7—C8—H8	120.6	C16—O19—C20	117.48 (14)
C10—C8—H8	120.6	O19—C20—H20A	109.5
C10—C9—C5	118.54 (16)	O19—C20—H20B	109.5
C10—C9—C4	119.12 (15)	H20A—C20—H20B	109.5
C5—C9—C4	122.33 (16)	O19—C20—H20C	109.5
O1—C10—C9	122.03 (15)	H20A—C20—H20C	109.5
O1—C10—C8	116.27 (15)	H20B—C20—H20C	109.5
C10—O1—C2—C3	−0.8 (2)	C4—C9—C10—O1	−0.9 (2)
C10—O1—C2—C13	177.25 (14)	C5—C9—C10—C8	−0.6 (3)
O1—C2—C3—O11	178.96 (15)	C4—C9—C10—C8	178.47 (16)
C13—C2—C3—O11	1.3 (3)	C7—C8—C10—O1	179.94 (15)
O1—C2—C3—C4	1.2 (2)	C7—C8—C10—C9	0.5 (3)
C13—C2—C3—C4	−176.51 (16)	C3—C2—C13—C18	−12.4 (3)
O11—C3—C4—O12	−1.0 (2)	O1—C2—C13—C18	169.72 (15)
C2—C3—C4—O12	176.88 (16)	C3—C2—C13—C14	166.24 (18)
O11—C3—C4—C9	−179.22 (14)	O1—C2—C13—C14	−11.6 (2)
C2—C3—C4—C9	−1.4 (2)	C18—C13—C14—C15	1.4 (3)
C9—C5—C6—C7	0.3 (3)	C2—C13—C14—C15	−177.35 (17)
C5—C6—C7—C8	−0.4 (3)	C13—C14—C15—C16	−1.6 (3)
C6—C7—C8—C10	0.0 (3)	C14—C15—C16—O19	−179.23 (17)
C6—C5—C9—C10	0.1 (3)	C14—C15—C16—C17	0.6 (3)
C6—C5—C9—C4	−178.88 (16)	O19—C16—C17—C18	−179.65 (17)
O12—C4—C9—C10	−176.95 (16)	C15—C16—C17—C18	0.6 (3)
C3—C4—C9—C10	1.2 (2)	C16—C17—C18—C13	−0.7 (3)
O12—C4—C9—C5	2.0 (3)	C14—C13—C18—C17	−0.2 (3)
C3—C4—C9—C5	−179.82 (16)	C2—C13—C18—C17	178.47 (17)
C2—O1—C10—C9	0.7 (2)	C17—C16—O19—C20	1.9 (3)
C2—O1—C10—C8	−178.72 (14)	C15—C16—O19—C20	−178.31 (16)
C5—C9—C10—O1	−179.96 (15)

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12	0.91 (3)	2.17 (3)	2.672 (2)	114 (2)
O11—H11···O12i	0.91 (3)	1.92 (3)	2.748 (2)	149 (2)
C20—H20B···Cg1ii	0.96	2.87	3.710 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O12	0.91 (3)	2.17 (3)	2.672 (2)	114 (2)
O11—H11⋯O12i	0.91 (3)	1.92 (3)	2.748 (2)	149 (2)
C20—H20B⋯Cg1ii	0.96	2.87	3.710 (2)	147

Symmetry codes: (i) ; (ii) .