Crystal structure of 2-(3,4-di­meth­oxy­phen­yl)-3-hy­droxy-4H-chromen-4-one

Yoo, J.S.; Lim, Y.; Koh, D.

doi:10.1107/S1600536814018212

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o999-o1000

doi:10.1107/S1600536814018212

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Crystal structure of 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one

Jin Sil Yoo,^a Yoongho Lim ^b and Dongsoo Koh ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea, and ^bDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 August 2014; accepted 8 August 2014; online 13 August 2014)

In the title compound, C₁₇H₁₄O₅, the dimethoxy-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 methoxy 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 intramolecular 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 R₂²(10) loops and C—H⋯O interactions connect the dimers into [010] chains.

Keywords: crystal structure; 4H-chromen-4-one; biological properties; flavonols; natural products.

CCDC reference: 1018484

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₄O₅
M_r = 298.28
Monoclinic, P 2₁ /n
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

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
9945 measured reflections
3442 independent reflections
2438 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.204
S = 1.20
3442 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.56 e Å⁻³

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) -x+1, -y+1, -z; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1018484

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018212/hb7265sup1.cif

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

checkCIF report

Experimental top

Synthesis and crystallization top

Chalcone (1 mmol, 284 mg) was suspended in 15 ml of MeOH / THF (2:1), and 0.5 mL NaOH (30% aq.) was added to produce a red solution, which was cooled to 0°C. To this reaction mixture, was added 1 ml H₂O₂ (32% aq.) and the solution was stirred for 2h at room temperature. The resulting solution was poured into water (100 ml) and was acidified with 3M HCl. The pale yellow precipitate obtained was filtered and washed with ethanol give the titled compound (57%). Recrystallization in the ethanol solvent gave orange blocks of the title compound (mp: 475-476K)

Refinement top

The H atoms were placed at calculated positions and refined as riding with C–H = 0.95 A [Uiso(H) = 1.2 Ueq(C)].

Results and discussion top

Flavonoids are one of secondary metabolites in plants with C6—C3—C6 skeleton, which include flavones, flavonols, chalcones and isoflavones. Variety of flanonols have been isolated from natural sources and syntheized (Bendaikha et al. 2014; Prescott et al. 2013), because they have shown wide spectrum of biological activities (Lee et al. 2014; Dias et al. 2013). Inspired by the important biological activities of flavonols, our research project has been focused on development of novel flavonols which show broad range of biological activities. Because it has been well established that the presence and position of hydroxy and methoxy substituents plays an important role in determining the biological activity of flavonoids (Singh et al. 2014), the title compound was synthesized and its crystal structure was determined. A starting material, chalcone, (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, was prepared by the previously reported methods (Yong et al. 2013). Flavonol was obtained by oxidative cyclization of the chalcone with H₂O₂ in alkaline methanol medium (Lee et al. 2014).

In the title compound, C₁₇H₁₄O₅, dimethoxy substituted benzene ring is twisted relative to 4H-chromenon skeleton by 5.2 (4)^o. The methoxy groups at C12 and C13 are tilted from benzene ring by 2.7 (3)^o and 8.9 (4)^o, respectively. In the crystal, pairs of O—H—O hydrogen bonds form inversion dimer with graph-set notation R₂²(10) (Marciniec et al. 2013). In addition, each molecule contains intramolecular O—H—O hydrogen bond with a S(5) motif. Examples of structures of flavonols have been published (Serdiuk et al., 2013; Yu et al., 2006).

Related literature top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure with intermolecular O—H···O hydrogen bonds shown as dashed lines

2-(3,4-Dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one top

Crystal data top

C₁₇H₁₄O₅	F(000) = 624
M_r = 298.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0768P)² + 1.2451P] where P = (F_o² + 2F_c²)/3
3442 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₇H₁₄O₅	V = 1383.6 (2) Å³
M_r = 298.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2009 (7) Å	µ = 0.11 mm⁻¹
b = 9.2917 (8) Å	T = 200 K
c = 18.2684 (15) Å	0.31 × 0.18 × 0.09 mm
β = 96.322 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2438 reflections with I > 2σ(I)
9945 measured reflections	R_int = 0.033
3442 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.20	Δρ_max = 0.41 e Å⁻³
3442 reflections	Δρ_min = −0.56 e Å⁻³
202 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+5/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+5/2, y+1/2, −z+1/2.

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Volume 70| Part 9| September 2014| Pages o999-o1000

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