Crystal structure of 2-(3,4-di-meth-oxy-phen-yl)-3-hy-droxy-4H-chromen-4-one.

In the title compound, C17H14O5, the dimeth-oxy-substituted benzene ring is twisted relative to the 4H-chromenon skeleton (r.m.s. deviation = 0.015 Å) by 5.2 (4)°. The C atoms of the meth-oxy groups lie close to the plane of their attached benzene ring [deviations = 0.036 (3) and 0.290 (3)Å for the meta and para substituents, respectively]. An intra-molecular O-H⋯O hydrogen bond closes an S(5) ring. In the cystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops and C-H⋯O inter-actions connect the dimers into [010] chains.

Related literature

For the syntheses and biological properties of flavonols, see: Lee et al. (2014 ▶); Singh et al. (2014 ▶); Dias et al. (2013 ▶); Yong et al. (2013 ▶). For flavonols in natural products, see: Bendaikha et al. (2014 ▶); Prescott et al. (2013 ▶). For related structures, see: Marciniec et al. (2013 ▶); Serdiuk et al. (2013 ▶); Yu et al. (2006 ▶).

Experimental

Crystal data

C17H14O5

M = 298.28

Monoclinic,

a = 8.2009 (7) Å

b = 9.2917 (8) Å

c = 18.2684 (15) Å

β = 96.322 (2)°

V = 1383.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.31 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9945 measured reflections

3442 independent reflections

2438 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.204

S = 1.20

3442 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.56 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, New_Global_Publ_Block. DOI: 10.1107/S1600536814018212/hb7265sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018212/hb7265Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814018212/hb7265fig1.tif

Mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814018212/hb7265fig2.tif

Part of the crystal structure with inter­molecular O—H⋯O hydrogen bonds shown as dashed lines

CCDC reference: 1018484

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

C17H14O5	F(000) = 624
Mr = 298.28	Dx = 1.432 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5723 reflections
a = 8.2009 (7) Å	θ = 2.2–28.3°
b = 9.2917 (8) Å	µ = 0.11 mm−1
c = 18.2684 (15) Å	T = 200 K
β = 96.322 (2)°	Block, orange
V = 1383.6 (2) Å3	0.31 × 0.18 × 0.09 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2438 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 28.3°, θmin = 2.2°
phi and ω scans	h = −10→8
9945 measured reflections	k = −12→10
3442 independent reflections	l = −24→23

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0768P)2 + 1.2451P] where P = (Fo2 + 2Fc2)/3
3442 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.56 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	0.4617 (3)	0.3933 (2)	−0.06661 (11)	0.0482 (5)
C1	0.5311 (3)	0.2734 (3)	−0.06091 (14)	0.0359 (5)
C2	0.4995 (3)	0.1608 (3)	−0.11530 (13)	0.0331 (5)
C3	0.3917 (3)	0.1776 (3)	−0.17952 (14)	0.0376 (6)
H3	0.3373	0.2669	−0.1893	0.045*
C4	0.3639 (3)	0.0662 (3)	−0.22855 (14)	0.0418 (6)
H4	0.2905	0.0787	−0.2721	0.050*
C5	0.4433 (3)	−0.0657 (3)	−0.21466 (14)	0.0415 (6)
H5	0.4236	−0.1426	−0.2488	0.050*
C6	0.5503 (3)	−0.0846 (3)	−0.15152 (14)	0.0366 (5)
H6	0.6038	−0.1743	−0.1417	0.044*
C7	0.5784 (3)	0.0295 (3)	−0.10267 (12)	0.0314 (5)
O2	0.6861 (2)	0.00521 (17)	−0.04197 (9)	0.0324 (4)
C8	0.7237 (3)	0.1100 (2)	0.00988 (12)	0.0294 (5)
C9	0.6471 (3)	0.2409 (3)	0.00173 (13)	0.0328 (5)
O3	0.6804 (2)	0.34504 (19)	0.05317 (11)	0.0446 (5)
H3A	0.6195	0.4164	0.0425	0.067*
C10	0.8434 (3)	0.0586 (2)	0.06893 (12)	0.0299 (5)
C11	0.8933 (3)	−0.0875 (2)	0.06779 (12)	0.0302 (5)
H11	0.8517	−0.1475	0.0280	0.036*
C12	1.0008 (3)	−0.1431 (2)	0.12337 (12)	0.0302 (5)
C13	1.0641 (3)	−0.0565 (3)	0.18262 (12)	0.0309 (5)
C14	1.0198 (3)	0.0875 (3)	0.18304 (14)	0.0359 (5)
H14	1.0646	0.1479	0.2221	0.043*
C15	0.9108 (3)	0.1445 (3)	0.12696 (14)	0.0348 (5)
H15	0.8818	0.2434	0.1282	0.042*
O4	1.0533 (2)	−0.28329 (18)	0.12628 (9)	0.0386 (4)
C16	0.9847 (4)	−0.3755 (3)	0.06895 (16)	0.0467 (7)
H16A	0.8652	−0.3785	0.0688	0.070*
H16B	1.0296	−0.4726	0.0770	0.070*
H16C	1.0119	−0.3389	0.0215	0.070*
O5	1.1652 (2)	−0.12376 (19)	0.23612 (9)	0.0387 (4)
C17	1.2109 (4)	−0.0443 (3)	0.30216 (14)	0.0456 (7)
H17A	1.2667	0.0445	0.2903	0.068*
H17B	1.2849	−0.1026	0.3360	0.068*
H17C	1.1124	−0.0204	0.3256	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0552 (12)	0.0343 (10)	0.0526 (11)	0.0138 (8)	−0.0047 (9)	0.0018 (8)
C1	0.0362 (12)	0.0309 (12)	0.0411 (13)	0.0041 (10)	0.0072 (10)	0.0040 (10)
C2	0.0320 (12)	0.0341 (12)	0.0337 (11)	0.0015 (9)	0.0064 (9)	0.0060 (9)
C3	0.0325 (12)	0.0419 (13)	0.0386 (13)	0.0033 (10)	0.0049 (10)	0.0057 (10)
C4	0.0348 (13)	0.0535 (16)	0.0364 (12)	−0.0016 (11)	0.0010 (10)	0.0084 (11)
C5	0.0385 (13)	0.0535 (16)	0.0310 (12)	−0.0045 (12)	−0.0021 (10)	−0.0052 (11)
C6	0.0367 (13)	0.0341 (12)	0.0387 (12)	0.0027 (10)	0.0032 (10)	−0.0021 (10)
C7	0.0275 (11)	0.0383 (12)	0.0284 (10)	−0.0015 (9)	0.0024 (8)	0.0025 (9)
O2	0.0334 (9)	0.0288 (8)	0.0338 (8)	0.0034 (6)	−0.0010 (7)	−0.0029 (6)
C8	0.0288 (11)	0.0274 (11)	0.0323 (11)	0.0008 (8)	0.0043 (9)	−0.0005 (8)
C9	0.0352 (12)	0.0279 (11)	0.0355 (12)	0.0019 (9)	0.0047 (9)	−0.0007 (9)
O3	0.0531 (12)	0.0278 (9)	0.0499 (11)	0.0098 (8)	−0.0076 (9)	−0.0076 (8)
C10	0.0287 (11)	0.0295 (11)	0.0319 (11)	0.0007 (9)	0.0056 (9)	−0.0028 (9)
C11	0.0295 (11)	0.0306 (11)	0.0305 (11)	0.0011 (9)	0.0033 (9)	−0.0020 (9)
C12	0.0307 (11)	0.0290 (11)	0.0304 (11)	0.0017 (9)	0.0019 (9)	−0.0008 (9)
C13	0.0289 (11)	0.0325 (12)	0.0312 (11)	−0.0004 (9)	0.0025 (9)	−0.0036 (9)
C14	0.0362 (12)	0.0346 (12)	0.0366 (12)	−0.0012 (10)	0.0020 (10)	−0.0068 (10)
C15	0.0348 (12)	0.0293 (11)	0.0392 (12)	0.0016 (9)	−0.0010 (10)	−0.0033 (9)
O4	0.0478 (10)	0.0286 (9)	0.0364 (9)	0.0067 (7)	−0.0086 (7)	−0.0043 (7)
C16	0.0587 (17)	0.0295 (12)	0.0469 (15)	0.0069 (12)	−0.0167 (13)	−0.0093 (11)
O5	0.0425 (10)	0.0384 (9)	0.0321 (8)	0.0018 (8)	−0.0089 (7)	−0.0028 (7)
C17	0.0534 (16)	0.0455 (15)	0.0351 (13)	−0.0058 (12)	−0.0086 (11)	−0.0064 (11)

O1—C1	1.250 (3)	C10—C15	1.392 (3)
C1—C9	1.437 (3)	C10—C11	1.418 (3)
C1—C2	1.447 (4)	C11—C12	1.370 (3)
C2—C7	1.388 (3)	C11—H11	0.9500
C2—C3	1.398 (3)	C12—O4	1.371 (3)
C3—C4	1.371 (4)	C12—C13	1.401 (3)
C3—H3	0.9500	C13—O5	1.362 (3)
C4—C5	1.397 (4)	C13—C14	1.387 (3)
C4—H4	0.9500	C14—C15	1.388 (3)
C5—C6	1.381 (3)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.388 (3)	O4—C16	1.420 (3)
C6—H6	0.9500	C16—H16A	0.9800
C7—O2	1.359 (3)	C16—H16B	0.9800
O2—C8	1.370 (3)	C16—H16C	0.9800
C8—C9	1.369 (3)	O5—C17	1.429 (3)
C8—C10	1.457 (3)	C17—H17A	0.9800
C9—O3	1.356 (3)	C17—H17B	0.9800
O3—H3A	0.8400	C17—H17C	0.9800
O1—C1—C9	120.6 (2)	C11—C10—C8	118.4 (2)
O1—C1—C2	122.8 (2)	C12—C11—C10	120.9 (2)
C9—C1—C2	116.6 (2)	C12—C11—H11	119.6
C7—C2—C3	118.5 (2)	C10—C11—H11	119.6
C7—C2—C1	118.5 (2)	C11—C12—O4	124.1 (2)
C3—C2—C1	123.0 (2)	C11—C12—C13	120.6 (2)
C4—C3—C2	120.5 (2)	O4—C12—C13	115.3 (2)
C4—C3—H3	119.7	O5—C13—C14	125.3 (2)
C2—C3—H3	119.7	O5—C13—C12	115.8 (2)
C3—C4—C5	120.2 (2)	C14—C13—C12	118.9 (2)
C3—C4—H4	119.9	C13—C14—C15	120.8 (2)
C5—C4—H4	119.9	C13—C14—H14	119.6
C6—C5—C4	120.2 (3)	C15—C14—H14	119.6
C6—C5—H5	119.9	C14—C15—C10	120.9 (2)
C4—C5—H5	119.9	C14—C15—H15	119.6
C5—C6—C7	119.0 (2)	C10—C15—H15	119.6
C5—C6—H6	120.5	C12—O4—C16	116.58 (18)
C7—C6—H6	120.5	O4—C16—H16A	109.5
O2—C7—C6	116.4 (2)	O4—C16—H16B	109.5
O2—C7—C2	122.0 (2)	H16A—C16—H16B	109.5
C6—C7—C2	121.5 (2)	O4—C16—H16C	109.5
C7—O2—C8	121.53 (18)	H16A—C16—H16C	109.5
C9—C8—O2	119.4 (2)	H16B—C16—H16C	109.5
C9—C8—C10	129.5 (2)	C13—O5—C17	116.8 (2)
O2—C8—C10	111.13 (19)	O5—C17—H17A	109.5
O3—C9—C8	120.2 (2)	O5—C17—H17B	109.5
O3—C9—C1	117.8 (2)	H17A—C17—H17B	109.5
C8—C9—C1	121.9 (2)	O5—C17—H17C	109.5
C9—O3—H3A	109.5	H17A—C17—H17C	109.5
C15—C10—C11	117.9 (2)	H17B—C17—H17C	109.5
C15—C10—C8	123.7 (2)
O1—C1—C2—C7	−177.7 (2)	C2—C1—C9—O3	179.3 (2)
C9—C1—C2—C7	1.8 (3)	O1—C1—C9—C8	179.3 (2)
O1—C1—C2—C3	1.5 (4)	C2—C1—C9—C8	−0.2 (4)
C9—C1—C2—C3	−179.1 (2)	C9—C8—C10—C15	−5.2 (4)
C7—C2—C3—C4	0.5 (4)	O2—C8—C10—C15	176.3 (2)
C1—C2—C3—C4	−178.7 (2)	C9—C8—C10—C11	174.2 (2)
C2—C3—C4—C5	0.0 (4)	O2—C8—C10—C11	−4.2 (3)
C3—C4—C5—C6	0.0 (4)	C15—C10—C11—C12	2.0 (3)
C4—C5—C6—C7	−0.5 (4)	C8—C10—C11—C12	−177.5 (2)
C5—C6—C7—O2	−179.3 (2)	C10—C11—C12—O4	179.4 (2)
C5—C6—C7—C2	1.0 (4)	C10—C11—C12—C13	−0.1 (3)
C3—C2—C7—O2	179.3 (2)	C11—C12—C13—O5	177.7 (2)
C1—C2—C7—O2	−1.5 (3)	O4—C12—C13—O5	−1.8 (3)
C3—C2—C7—C6	−1.0 (4)	C11—C12—C13—C14	−1.8 (3)
C1—C2—C7—C6	178.2 (2)	O4—C12—C13—C14	178.6 (2)
C6—C7—O2—C8	179.8 (2)	O5—C13—C14—C15	−177.6 (2)
C2—C7—O2—C8	−0.5 (3)	C12—C13—C14—C15	1.9 (4)
C7—O2—C8—C9	2.1 (3)	C13—C14—C15—C10	−0.1 (4)
C7—O2—C8—C10	−179.22 (19)	C11—C10—C15—C14	−1.9 (4)
O2—C8—C9—O3	178.8 (2)	C8—C10—C15—C14	177.6 (2)
C10—C8—C9—O3	0.5 (4)	C11—C12—O4—C16	−2.7 (4)
O2—C8—C9—C1	−1.8 (4)	C13—C12—O4—C16	176.9 (2)
C10—C8—C9—C1	179.9 (2)	C14—C13—O5—C17	8.9 (3)
O1—C1—C9—O3	−1.3 (4)	C12—C13—O5—C17	−170.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.84	2.26	2.710 (3)	113
O3—H3A···O1i	0.84	1.96	2.719 (3)	150
C17—H17A···O4ii	0.98	2.56	3.283 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1	0.84	2.26	2.710 (3)	113
O3—H3A⋯O1i	0.84	1.96	2.719 (3)	150
C17—H17A⋯O4ii	0.98	2.56	3.283 (3)	130

Symmetry codes: (i) ; (ii) .