3-Hy­droxy-2-(4-hy­droxy­phen­yl)-4H-chromen-4-one

Wera, M.; Pivovarenko, V.G.; Błażejowski, J.

doi:10.1107/S1600536810053407

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o264-o265

doi:10.1107/S1600536810053407

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3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Michał Wera,^a Vasyl G. Pivovarenko ^b and Jerzy Błażejowski ^a ^*

^aFaculty of Chemistry, University of Gdańsk, J. Sobieskiego 18, 80-952 Gdańsk, Poland, and ^bFaculty of Chemistry, Kyiv Taras Shevchenko National University, Volodymyrska 64, 01033 Kyiv, Ukraine
^*Correspondence e-mail: bla@chem.univ.gda.pl

(Received 30 November 2010; accepted 20 December 2010; online 8 January 2011)

In the title compound, C₁₅H₁₀O₄, the benzene ring is twisted at an angle of 20.7 (1)° relative to the 4H-chromene skeleton. In the crystal, adjacent molecules 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.

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_r = 254.23
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.155
S = 0.84
1979 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053407/xu5114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053407/xu5114Isup2.hkl

checkCIF report

Comment top

Flavones (derivatives of 2-phenyl-4H-chromen-4-one) appear in numerous natural systems and have been comprehensively investigated in view of their antioxidant features (Nijveldt et al., 2001). Related to flavones, 3-hydroxy-2-phenyl-4H-chromen-4-one (flavonols) exhibit dual fluorescence in the condensed phases resulting from the Excited State Intramolecular Proton Transfer (ESIPT) (Sengupta & Kasha, 1979). In flavonols this phenomenon is strongly affected by molecules from their environment, which makes the compounds interesting fluorescent sensors for analytical applications in chemistry, biology, biochemistry, ecology and medicine (Klymchenko & Demchenko, 2003; Demchenko, 2009; Choulier et al., 2010). Continuing our investigations into the physical chemistry of flavonols (Bader et al., 2003; Roshal et al., 2003; Pivovarenko et al., 2004), we present the crystal structure of 3-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one in the hope that its structural and fluorescent features will appear interesting and helpful in its practical applications.

In the title compound (Fig. 1), the bond lengths and angles characterizing the geometry of the 2-phenyl-4H-chromen-4-one moiety are typical of this group of compounds (Etter et al., 1986; Kumar et al., 1998; Waller et al., 2003). With respective average deviations from planarity of 0.0187 (1)° and 0.0041 (1)°, the 4H-chromene and benzene ring systems are oriented at a dihedral angle of 20.7 (1)° (in the case of flavonol this angle is 5.5 (1)° (Etter et al., 1986)). The mean planes of the adjacent 4H-chromen-4-one moieties are either parallel (remain at an angle of 0.0 (1)°) or inclined at 20.9 (1)°.

The crystal structure of the title compound is stabilized by a network of O—H···O (Aakeröy et al., 1992) (Table 1, Fig. 2) and C—H···O (Novoa et al., 2006) (Table 1, Fig. 2) hydrogen bonds, and by non-specific dispersive interactions. Each of the two OH groups is involved in hydrogen bonds as H atom acceptor and donor. The O11—H11···O12 intramolecular hydrogen bond (Table 1, Figs. 1 and 2) is the one involved in the ESIPT phenomenon characteristic of flavonols (Sengupta & Kasha, 1979).

Related literature top

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 top

The title compound was synthesized in two steps. First, 3-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one was prepared by alkaline condensation of 4-methoxybenzaldehyde with 1-(2-hydroxyphenyl)ethanone and subsequent oxidative heterocyclization of the product with hydrogen peroxide (the light green-yellow precipitate of the product was recrystallized twice from a 1% solution of acetic acid in ethanol) (Bader et al., 2003). Next, the 3-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one thus obtained was converted to 3-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one by maintaining a solution of the former compound in molten pyridinium chloride at 495 K for 20 minutes, then cooling the reactant mixture, and pouring it into 1% aqueous HCl. Pale brown crystals suitable for X-ray investigations were grown from DMF solutions of the filtered precipitate of the final product (m.p. = 557–558 K; lit. 555–558 K (Sobottka et al., 2000)).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids are drawn at the 25% probability level, and H atoms are shown as small spheres of arbitrary radius. The O—H···O hydrogen bond is indicated by a dashed line.
	Fig. 2. The arrangement of the molecules in the crystal structure. The O–H···O and C–H···O hydrogen bonds are represented by dashed lines. H atoms not involved in interactions have been omitted. [Symmetry codes: (i) x, –y + 1/2, z – 1/2; (ii) x – 1, –y + 1/2, z + 1/2; (iii) –x + 1, y + 1/2, –z + 3/2.]

3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one top

Crystal data top

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

Data collection top

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 monochromator	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 top

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)

Crystal data top

C₁₅H₁₀O₄	V = 1121.09 (17) Å³
M_r = 254.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.7897 (3) Å	µ = 0.11 mm⁻¹
b = 17.6380 (15) Å	T = 295 K
c = 16.7745 (16) Å	0.6 × 0.2 × 0.2 mm
β = 90.968 (9)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	Δρ_max = 0.28 e Å⁻³
1979 reflections	Δρ_min = −0.31 e Å⁻³
179 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	0.2942 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀O₄
M_r	254.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	3.7897 (3), 17.6380 (15), 16.7745 (16)
β (°)	90.968 (9)
V (Å³)	1121.09 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.6 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.329, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9273, 1979, 920
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.155, 0.84
No. of reflections	1979
No. of parameters	179
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements

This study was financed by the State Funds for Scientific Research (grant DS/8220–4-0087–0).

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