Literature DB >> 21522957

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

Michał Wera, Vasyl G Pivovarenko, Jerzy Błażejowski.

Abstract

In the title compound, C(15)H(10)O(4), the benzene ring is twisted at an angle of 20.7 (1)° relative to the 4H-chromene skeleton. In the crystal, adjacent mol-ecules are linked via a network of O-H⋯O and C-H⋯O hydrogen bonds. The mean planes of adjacent 4H-chromene moieties are parallel or oriented at an angle of 20.9 (1)° in the crystal structure.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 21522957 PMCID： PMC3051623 DOI： 10.1107/S1600536810053407

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to the properties of flavones (derivatives of 2-phenyl-4H-chromen-4-one) and fluorescence of flavonols (derivatives of 3-hydroxy-2-phenyl-4H-chromen-4-one), see: Bader et al. (2003 ▶); Choulier et al. (2010 ▶); Demchenko (2009 ▶); Klymchenko & Demchenko (2003 ▶); Nijveldt et al. (2001 ▶); Pivovarenko et al. (2004 ▶); Roshal et al. (2003 ▶); Sengupta & Kasha (1979 ▶). For related structures, see: Etter et al. (1986 ▶); Kumar et al. (1998 ▶); Waller et al. (2003 ▶). For intermolecular interactions, see: Aakeröy et al. (1992 ▶); Novoa et al. (2006 ▶). For the synthesis, see: Bader et al. (2003 ▶); Sobottka et al. (2000 ▶).

Experimental

Crystal data

C15H10O4 M = 254.23 Monoclinic, a = 3.7897 (3) Å b = 17.6380 (15) Å c = 16.7745 (16) Å β = 90.968 (9)° V = 1121.09 (17) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 295 K 0.6 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.329, T max = 1.000 9273 measured reflections 1979 independent reflections 920 reflections with I > 2σ(I) R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.155 S = 0.84 1979 reflections 179 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.28 e Å−3 Δρmin = −0.31 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/S1600536810053407/xu5114sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053407/xu5114Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₀O₄	F(000) = 528
M_r = 254.23	D_x = 1.506 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1979 reflections
a = 3.7897 (3) Å	θ = 3.4–25.0°
b = 17.6380 (15) Å	µ = 0.11 mm⁻¹
c = 16.7745 (16) Å	T = 295 K
β = 90.968 (9)°	Needle, pale brown
V = 1121.09 (17) Å³	0.6 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	1979 independent reflections
Radiation source: Enhance (Mo) X-ray Source	920 reflections with I > 2σ(I)
graphite	R_int = 0.075
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −20→20
T_min = 0.329, T_max = 1.000	l = −19→19
9273 measured reflections

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0893P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
1979 reflections	Δρ_max = 0.28 e Å⁻³
179 parameters	Δρ_min = −0.31 e Å⁻³
0 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: 0.011 (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	U_iso*/U_eq
O1	0.2942 (6)	0.46752 (12)	0.80136 (13)	0.0490 (7)
C2	0.2180 (8)	0.39182 (18)	0.8026 (2)	0.0416 (9)
C3	0.2703 (9)	0.34891 (18)	0.7361 (2)	0.0430 (9)
C4	0.4184 (9)	0.3797 (2)	0.6655 (2)	0.0470 (9)
C5	0.6344 (8)	0.4972 (2)	0.6004 (2)	0.0507 (10)
H5	0.6885	0.4702	0.5546	0.061*
C6	0.6924 (9)	0.5739 (2)	0.6035 (2)	0.0570 (10)
H6	0.7830	0.5990	0.5595	0.068*
C7	0.6161 (10)	0.6139 (2)	0.6719 (2)	0.0602 (11)
H7	0.6540	0.6660	0.6732	0.072*
C8	0.4854 (9)	0.5782 (2)	0.7379 (2)	0.0538 (10)
H8	0.4373	0.6054	0.7839	0.065*
C9	0.4944 (8)	0.45958 (18)	0.66600 (19)	0.0423 (9)
C10	0.4267 (8)	0.50063 (19)	0.7343 (2)	0.0431 (9)
O11	0.1984 (8)	0.27345 (14)	0.73772 (16)	0.0663 (9)
H11	0.167 (12)	0.257 (3)	0.692 (3)	0.099*
O12	0.4757 (7)	0.33773 (14)	0.60629 (15)	0.0662 (8)
C13	0.0981 (8)	0.36660 (19)	0.8811 (2)	0.0418 (9)
C14	0.1704 (9)	0.4109 (2)	0.9483 (2)	0.0488 (9)
H14	0.2816	0.4575	0.9424	0.059*
C15	0.0792 (9)	0.3865 (2)	1.0232 (2)	0.0514 (10)
H15	0.1291	0.4166	1.0675	0.062*
C16	−0.0861 (9)	0.3175 (2)	1.0325 (2)	0.0479 (9)
C17	−0.1637 (9)	0.2732 (2)	0.9672 (2)	0.0502 (10)
H17	−0.2771	0.2269	0.9735	0.060*
C18	−0.0727 (8)	0.29790 (19)	0.8922 (2)	0.0463 (9)
H18	−0.1270	0.2678	0.8481	0.056*
O19	−0.1701 (7)	0.29545 (15)	1.10853 (15)	0.0614 (8)
H19	−0.285 (11)	0.250 (3)	1.110 (3)	0.092*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0679 (16)	0.0378 (15)	0.0414 (16)	−0.0017 (11)	0.0061 (12)	0.0001 (11)
C2	0.053 (2)	0.036 (2)	0.036 (2)	−0.0001 (15)	−0.0006 (16)	0.0032 (16)
C3	0.061 (2)	0.033 (2)	0.035 (2)	0.0025 (16)	−0.0020 (17)	0.0000 (16)
C4	0.057 (2)	0.045 (2)	0.039 (2)	0.0033 (17)	−0.0027 (17)	−0.0001 (17)
C5	0.061 (2)	0.051 (3)	0.040 (2)	0.0038 (18)	0.0021 (18)	0.0014 (17)
C6	0.067 (2)	0.055 (3)	0.049 (3)	−0.003 (2)	0.0049 (19)	0.0112 (19)
C7	0.080 (3)	0.044 (2)	0.057 (3)	−0.007 (2)	0.002 (2)	0.007 (2)
C8	0.068 (2)	0.043 (2)	0.051 (3)	−0.0048 (19)	0.0036 (19)	−0.0028 (18)
C9	0.049 (2)	0.040 (2)	0.038 (2)	0.0041 (16)	0.0008 (17)	0.0045 (16)
C10	0.048 (2)	0.044 (2)	0.036 (2)	0.0011 (17)	0.0008 (17)	0.0049 (16)
O11	0.122 (2)	0.0371 (16)	0.0400 (17)	−0.0105 (14)	0.0089 (16)	−0.0016 (12)
O12	0.111 (2)	0.0486 (16)	0.0399 (17)	0.0058 (14)	0.0140 (14)	−0.0030 (13)
C13	0.048 (2)	0.037 (2)	0.040 (2)	0.0051 (16)	−0.0046 (16)	−0.0003 (15)
C14	0.061 (2)	0.040 (2)	0.045 (2)	−0.0006 (17)	0.0034 (18)	0.0014 (18)
C15	0.071 (3)	0.044 (2)	0.039 (2)	0.0022 (18)	0.0014 (18)	−0.0035 (17)
C16	0.057 (2)	0.044 (2)	0.043 (2)	0.0084 (18)	0.0049 (17)	0.0009 (17)
C17	0.061 (2)	0.042 (2)	0.047 (3)	−0.0046 (17)	0.0065 (18)	0.0012 (17)
C18	0.056 (2)	0.042 (2)	0.042 (2)	−0.0007 (16)	0.0041 (17)	−0.0033 (16)
O19	0.091 (2)	0.0553 (18)	0.0380 (17)	−0.0007 (14)	0.0134 (14)	0.0056 (13)

O1—C2	1.366 (4)	C8—H8	0.9300
O1—C10	1.370 (4)	C9—C10	1.383 (5)
C2—C3	1.365 (4)	O11—H11	0.82 (5)
C2—C13	1.469 (4)	C13—C18	1.388 (4)
C3—O11	1.359 (4)	C13—C14	1.394 (5)
C3—C4	1.427 (5)	C14—C15	1.378 (5)
C4—O12	1.261 (4)	C14—H14	0.9300
C4—C9	1.438 (5)	C15—C16	1.379 (5)
C5—C6	1.372 (5)	C15—H15	0.9300
C5—C9	1.397 (5)	C16—C17	1.373 (5)
C5—H5	0.9300	C16—O19	1.375 (4)
C6—C7	1.381 (5)	C17—C18	1.381 (5)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.374 (5)	C18—H18	0.9300
C7—H7	0.9300	O19—H19	0.91 (4)
C8—C10	1.387 (5)

C2—O1—C10	120.6 (3)	C5—C9—C4	122.7 (3)
O1—C2—C3	119.7 (3)	O1—C10—C9	122.2 (3)
O1—C2—C13	112.2 (3)	O1—C10—C8	116.5 (3)
C3—C2—C13	128.0 (3)	C9—C10—C8	121.3 (3)
O11—C3—C2	119.7 (3)	C3—O11—H11	110 (3)
O11—C3—C4	118.1 (3)	C18—C13—C14	117.8 (3)
C2—C3—C4	122.1 (3)	C18—C13—C2	122.4 (3)
O12—C4—C3	120.4 (3)	C14—C13—C2	119.7 (3)
O12—C4—C9	122.8 (3)	C15—C14—C13	120.9 (3)
C3—C4—C9	116.7 (3)	C15—C14—H14	119.6
C6—C5—C9	120.1 (3)	C13—C14—H14	119.6
C6—C5—H5	119.9	C14—C15—C16	120.0 (3)
C9—C5—H5	119.9	C14—C15—H15	120.0
C5—C6—C7	119.9 (4)	C16—C15—H15	120.0
C5—C6—H6	120.0	C17—C16—O19	122.0 (3)
C7—C6—H6	120.0	C17—C16—C15	120.2 (3)
C8—C7—C6	121.3 (4)	O19—C16—C15	117.8 (3)
C8—C7—H7	119.4	C16—C17—C18	119.6 (3)
C6—C7—H7	119.4	C16—C17—H17	120.2
C7—C8—C10	118.5 (4)	C18—C17—H17	120.2
C7—C8—H8	120.8	C17—C18—C13	121.4 (3)
C10—C8—H8	120.8	C17—C18—H18	119.3
C10—C9—C5	118.8 (3)	C13—C18—H18	119.3
C10—C9—C4	118.5 (3)	C16—O19—H19	113 (3)

C10—O1—C2—C3	−0.8 (4)	C5—C9—C10—O1	−179.1 (3)
C10—O1—C2—C13	176.8 (3)	C4—C9—C10—O1	0.8 (5)
O1—C2—C3—O11	179.2 (3)	C5—C9—C10—C8	1.9 (5)
C13—C2—C3—O11	2.1 (5)	C4—C9—C10—C8	−178.3 (3)
O1—C2—C3—C4	2.9 (5)	C7—C8—C10—O1	−179.6 (3)
C13—C2—C3—C4	−174.2 (3)	C7—C8—C10—C9	−0.5 (5)
O11—C3—C4—O12	0.9 (5)	O1—C2—C13—C18	164.2 (3)
C2—C3—C4—O12	177.2 (3)	C3—C2—C13—C18	−18.5 (5)
O11—C3—C4—C9	−179.4 (3)	O1—C2—C13—C14	−18.9 (4)
C2—C3—C4—C9	−3.1 (5)	C3—C2—C13—C14	158.5 (3)
C9—C5—C6—C7	0.8 (5)	C18—C13—C14—C15	0.9 (5)
C5—C6—C7—C8	0.6 (6)	C2—C13—C14—C15	−176.2 (3)
C6—C7—C8—C10	−0.8 (6)	C13—C14—C15—C16	0.0 (5)
C6—C5—C9—C10	−2.0 (5)	C14—C15—C16—C17	−0.7 (5)
C6—C5—C9—C4	178.2 (3)	C14—C15—C16—O19	179.7 (3)
O12—C4—C9—C10	−179.1 (3)	O19—C16—C17—C18	−179.8 (3)
C3—C4—C9—C10	1.2 (4)	C15—C16—C17—C18	0.6 (5)
O12—C4—C9—C5	0.7 (5)	C16—C17—C18—C13	0.3 (5)
C3—C4—C9—C5	−178.9 (3)	C14—C13—C18—C17	−1.0 (5)
C2—O1—C10—C9	−1.1 (4)	C2—C13—C18—C17	176.0 (3)
C2—O1—C10—C8	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12	0.83 (5)	2.35 (5)	2.707 (4)	107 (4)
O11—H11···O19ⁱ	0.83 (5)	2.10 (5)	2.832 (4)	148 (4)
O19—H19···O12ⁱⁱ	0.91 (5)	1.79 (5)	2.705 (4)	176 (5)
C7—H7···O11ⁱⁱⁱ	0.93	2.47	3.267 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O19ⁱ	0.83 (5)	2.10 (5)	2.832 (4)	148 (4)
O19—H19⋯O12ⁱⁱ	0.91 (5)	1.79 (5)	2.705 (4)	176 (5)
C7—H7⋯O11ⁱⁱⁱ	0.93	2.47	3.267 (4)	144

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

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