2-(5,7-Di­hydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzo­quinone (isoflavone­quinone)

Aree, T.; Tip-pyang, S.; Seesukphronrarak, S.; Chaichit, N.

doi:10.1107/S1600536803003684

2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone (isoflavonequinone)

T. Aree, S. Tip-pyang, S. Seesukphronrarak and N. Chaichit

In the title molecule, 5,7-dihydroxy-4′-methoxyisoflavonequinone, C₁₆H₁₀O₇, the dihedral angle between the chromene moiety and the cyclohexa-1,4-diene ring is 51.72 (5)°. The molecular structure is stabilized by an intramolecular O—H

O hydrogen bond. In the crystal structure, intermolecular O—H

O hydrogen bonds link the molecules to form chains along the c axis. Adjacent molecular chains are linked along the b axis by C—H

O hydrogen bonds to form a network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003684/ci6202sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003684/ci6202Isup2.hkl Contains datablock I

CCDC reference: 206794

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.125
Data-to-parameter ratio = 15.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.50
         From the CIF: _reflns_number_total               3781
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4011
         Completeness (_total/calc)             94.27%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Siemens, 1996) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON and SHELXL97.

2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone top

Crystal data top

C₁₆H₁₀O₇	F(000) = 648
M_r = 314.24	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/a	Melting point: decomposed at 523 K K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 12.6447 (2) Å	Cell parameters from 75 reflections
b = 7.7044 (1) Å	θ = 1.5–30.5°
c = 13.5573 (1) Å	µ = 0.13 mm⁻¹
β = 92.103 (1)°	T = 295 K
V = 1319.86 (3) Å³	Needle, yellow
Z = 4	0.5 × 0.2 × 0.1 mm

Data collection top

SMART CCD diffractometer	3781 independent reflections
Radiation source: fine-focus sealed tube	2899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 30.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→15
T_min = 0.970, T_max = 0.987	k = −10→10
9429 measured reflections	l = −16→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0661P)² + 0.2705P] where P = (F_o² + 2F_c²)/3
3781 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

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	0.40673 (7)	0.26346 (15)	0.64956 (6)	0.0414 (2)
O2	0.11495 (7)	0.06300 (14)	0.57570 (7)	0.0402 (2)
O3	0.08836 (8)	0.00122 (16)	0.76029 (8)	0.0480 (3)
H3O	0.078 (2)	0.013 (3)	0.6910 (19)	0.094 (8)*
O4	0.36494 (10)	0.1724 (2)	0.98672 (8)	0.0679 (4)
H4O	0.325 (2)	0.132 (3)	1.029 (2)	0.095 (9)*
O5	0.35210 (8)	0.05104 (17)	0.18676 (7)	0.0532 (3)
O6	0.16852 (8)	0.16144 (16)	0.11319 (7)	0.0467 (3)
O7	0.09250 (8)	0.34275 (14)	0.43611 (7)	0.0423 (2)
C2	0.37182 (10)	0.24859 (19)	0.55453 (9)	0.0356 (3)
H2	0.4224 (13)	0.287 (2)	0.5120 (13)	0.046 (4)*
C3	0.27620 (9)	0.18883 (17)	0.52454 (8)	0.0311 (2)
C4	0.20287 (9)	0.12771 (16)	0.59776 (9)	0.0298 (2)
C5	0.18383 (10)	0.07363 (17)	0.77835 (9)	0.0334 (3)
C6	0.22462 (11)	0.0808 (2)	0.87443 (9)	0.0398 (3)
H6	0.1842 (15)	0.032 (2)	0.9267 (15)	0.058 (5)*
C7	0.32257 (12)	0.1578 (2)	0.89376 (9)	0.0441 (3)
C8	0.38381 (12)	0.2208 (2)	0.81853 (10)	0.0451 (3)
H8	0.4552 (16)	0.268 (3)	0.8314 (15)	0.066 (6)*
C9	0.34276 (10)	0.20696 (18)	0.72299 (9)	0.0338 (3)
C10	0.24274 (9)	0.13899 (16)	0.69937 (8)	0.0299 (2)
C11	0.06753 (14)	0.2245 (3)	0.07344 (12)	0.0548 (4)
H11A	0.0082 (19)	0.152 (3)	0.0981 (17)	0.078 (7)*
H11B	0.0577 (17)	0.353 (3)	0.0908 (17)	0.076 (7)*
H11C	0.0757 (18)	0.216 (3)	0.0057 (19)	0.082 (7)*
C1'	0.24900 (9)	0.17788 (17)	0.41753 (8)	0.0313 (3)
C2'	0.31432 (10)	0.10665 (19)	0.35280 (9)	0.0368 (3)
H2'	0.3826 (14)	0.058 (2)	0.3738 (13)	0.048 (4)*
C3'	0.28946 (10)	0.10552 (19)	0.24592 (9)	0.0371 (3)
C4'	0.18355 (10)	0.17454 (18)	0.21166 (9)	0.0352 (3)
C5'	0.11710 (10)	0.24311 (19)	0.27543 (9)	0.0365 (3)
H5'	0.0516 (14)	0.292 (2)	0.2571 (13)	0.049 (5)*
C6'	0.14703 (9)	0.25907 (17)	0.38066 (9)	0.0323 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (4)	0.0668 (7)	0.0232 (4)	−0.0134 (4)	0.0012 (3)	0.0063 (4)
O2	0.0384 (5)	0.0523 (6)	0.0299 (4)	−0.0119 (4)	0.0010 (4)	−0.0018 (4)
O3	0.0408 (5)	0.0697 (7)	0.0339 (5)	−0.0177 (5)	0.0057 (4)	0.0043 (5)
O4	0.0609 (7)	0.1222 (12)	0.0204 (5)	−0.0271 (8)	−0.0015 (5)	0.0023 (6)
O5	0.0470 (6)	0.0835 (8)	0.0297 (5)	0.0121 (5)	0.0104 (4)	−0.0039 (5)
O6	0.0452 (5)	0.0721 (7)	0.0226 (4)	0.0027 (5)	−0.0017 (4)	−0.0012 (4)
O7	0.0425 (5)	0.0519 (6)	0.0328 (5)	0.0068 (4)	0.0070 (4)	−0.0032 (4)
C2	0.0334 (6)	0.0504 (8)	0.0232 (5)	−0.0024 (5)	0.0038 (5)	0.0057 (5)
C3	0.0337 (6)	0.0386 (6)	0.0211 (5)	0.0003 (5)	0.0028 (4)	0.0017 (4)
C4	0.0330 (5)	0.0330 (6)	0.0235 (5)	−0.0003 (4)	0.0034 (4)	−0.0010 (4)
C5	0.0338 (6)	0.0395 (7)	0.0273 (5)	−0.0030 (5)	0.0067 (4)	0.0001 (5)
C6	0.0425 (7)	0.0537 (8)	0.0238 (5)	−0.0041 (6)	0.0097 (5)	0.0011 (5)
C7	0.0468 (7)	0.0646 (9)	0.0208 (5)	−0.0049 (7)	0.0008 (5)	−0.0001 (6)
C8	0.0395 (7)	0.0698 (10)	0.0258 (6)	−0.0134 (7)	−0.0009 (5)	0.0016 (6)
C9	0.0334 (6)	0.0452 (7)	0.0231 (5)	−0.0048 (5)	0.0045 (4)	0.0025 (5)
C10	0.0323 (5)	0.0356 (6)	0.0220 (5)	−0.0015 (5)	0.0037 (4)	−0.0005 (4)
C11	0.0488 (9)	0.0860 (14)	0.0292 (7)	0.0050 (9)	−0.0061 (6)	0.0014 (7)
C1'	0.0334 (6)	0.0385 (6)	0.0221 (5)	−0.0034 (5)	0.0024 (4)	0.0020 (4)
C2'	0.0338 (6)	0.0515 (8)	0.0253 (5)	0.0032 (5)	0.0018 (5)	0.0014 (5)
C3'	0.0376 (6)	0.0495 (8)	0.0246 (5)	−0.0010 (5)	0.0052 (5)	0.0004 (5)
C4'	0.0375 (6)	0.0456 (7)	0.0225 (5)	−0.0060 (5)	−0.0002 (4)	0.0010 (5)
C5'	0.0320 (6)	0.0492 (8)	0.0281 (6)	−0.0024 (5)	−0.0004 (5)	0.0009 (5)
C6'	0.0318 (6)	0.0397 (7)	0.0255 (5)	−0.0045 (5)	0.0038 (4)	0.0010 (5)

Geometric parameters (Å, º) top

O1—C2	1.3513 (14)	C6—C7	1.389 (2)
O1—C9	1.3761 (14)	C6—H6	0.96 (2)
O2—C4	1.2448 (15)	C7—C8	1.3905 (19)
O3—C5	1.3442 (16)	C8—C9	1.3816 (17)
O3—H3O	0.95 (3)	C8—H8	0.98 (2)
O4—C7	1.3559 (16)	C9—C10	1.3953 (17)
O4—H4O	0.84 (3)	C11—H11A	1.00 (2)
O5—C3'	1.2221 (16)	C11—H11B	1.02 (2)
O6—C4'	1.3453 (14)	C11—H11C	0.93 (2)
O6—C11	1.4513 (19)	C1'—C2'	1.3442 (17)
O7—C6'	1.2223 (15)	C1'—C6'	1.5021 (17)
C2—C3	1.3428 (17)	C2'—C3'	1.4713 (17)
C2—H2	0.926 (18)	C2'—H2'	0.973 (17)
C3—C4	1.4610 (16)	C3'—C4'	1.4988 (18)
C3—C1'	1.4811 (15)	C4'—C5'	1.3364 (18)
C4—C10	1.4519 (15)	C5'—C6'	1.4677 (16)
C5—C6	1.3843 (17)	C5'—H5'	0.934 (17)
C5—C10	1.4190 (16)

C2—O1—C9	118.87 (10)	C9—C10—C5	117.16 (11)
C5—O3—H3O	103.2 (15)	C9—C10—C4	121.37 (10)
C7—O4—H4O	112.1 (19)	C5—C10—C4	121.41 (11)
C4'—O6—C11	115.70 (11)	O6—C11—H11A	110.4 (13)
C3—C2—O1	125.22 (11)	O6—C11—H11B	110.5 (12)
C3—C2—H2	123.8 (10)	H11A—C11—H11B	111.2 (18)
O1—C2—H2	111.0 (10)	O6—C11—H11C	102.3 (14)
C2—C3—C4	119.45 (10)	H11A—C11—H11C	113.6 (19)
C2—C3—C1'	119.36 (10)	H11B—C11—H11C	108.5 (19)
C4—C3—C1'	121.12 (10)	C2'—C1'—C3	122.45 (11)
O2—C4—C10	121.86 (10)	C2'—C1'—C6'	119.56 (11)
O2—C4—C3	123.32 (11)	C3—C1'—C6'	117.90 (10)
C10—C4—C3	114.73 (10)	C1'—C2'—C3'	122.08 (12)
O3—C5—C6	119.28 (11)	C1'—C2'—H2'	121.6 (10)
O3—C5—C10	120.17 (11)	C3'—C2'—H2'	116.2 (10)
C6—C5—C10	120.54 (12)	O5—C3'—C2'	121.88 (12)
C5—C6—C7	119.56 (11)	O5—C3'—C4'	120.78 (12)
C5—C6—H6	119.1 (11)	C2'—C3'—C4'	117.35 (11)
C7—C6—H6	121.3 (11)	C5'—C4'—O6	127.04 (12)
O4—C7—C6	122.01 (12)	C5'—C4'—C3'	121.04 (11)
O4—C7—C8	116.17 (13)	O6—C4'—C3'	111.90 (11)
C6—C7—C8	121.81 (12)	C4'—C5'—C6'	121.08 (12)
C9—C8—C7	117.43 (13)	C4'—C5'—H5'	124.0 (11)
C9—C8—H8	120.4 (12)	C6'—C5'—H5'	114.8 (11)
C7—C8—H8	122.1 (12)	O7—C6'—C5'	120.72 (12)
O1—C9—C8	116.31 (11)	O7—C6'—C1'	120.78 (11)
O1—C9—C10	120.30 (10)	C5'—C6'—C1'	118.43 (11)
C8—C9—C10	123.38 (11)

C9—O1—C2—C3	3.0 (2)	C3—C4—C10—C9	1.29 (18)
O1—C2—C3—C4	−2.4 (2)	O2—C4—C10—C5	1.15 (19)
O1—C2—C3—C1'	−179.34 (12)	C3—C4—C10—C5	−175.58 (12)
C2—C3—C4—O2	−176.52 (13)	C2—C3—C1'—C2'	47.86 (19)
C1'—C3—C4—O2	0.40 (19)	C4—C3—C1'—C2'	−129.06 (14)
C2—C3—C4—C10	0.16 (18)	C2—C3—C1'—C6'	−128.63 (14)
C1'—C3—C4—C10	177.08 (11)	C4—C3—C1'—C6'	54.44 (17)
O3—C5—C6—C7	−179.07 (14)	C3—C1'—C2'—C3'	−176.32 (12)
C10—C5—C6—C7	2.1 (2)	C6'—C1'—C2'—C3'	0.1 (2)
C5—C6—C7—O4	178.21 (15)	C1'—C2'—C3'—O5	175.06 (15)
C5—C6—C7—C8	−3.2 (2)	C1'—C2'—C3'—C4'	−4.8 (2)
O4—C7—C8—C9	179.78 (15)	C11—O6—C4'—C5'	−2.0 (2)
C6—C7—C8—C9	1.1 (3)	C11—O6—C4'—C3'	179.67 (14)
C2—O1—C9—C8	178.19 (13)	O5—C3'—C4'—C5'	−176.25 (15)
C2—O1—C9—C10	−1.3 (2)	C2'—C3'—C4'—C5'	3.6 (2)
C7—C8—C9—O1	−177.33 (14)	O5—C3'—C4'—O6	2.2 (2)
C7—C8—C9—C10	2.2 (2)	C2'—C3'—C4'—O6	−177.90 (12)
O1—C9—C10—C5	176.27 (12)	O6—C4'—C5'—C6'	−175.94 (13)
C8—C9—C10—C5	−3.2 (2)	C3'—C4'—C5'—C6'	2.3 (2)
O1—C9—C10—C4	−0.7 (2)	C4'—C5'—C6'—O7	169.91 (13)
C8—C9—C10—C4	179.78 (13)	C4'—C5'—C6'—C1'	−7.02 (19)
O3—C5—C10—C9	−177.83 (12)	C2'—C1'—C6'—O7	−171.13 (13)
C6—C5—C10—C9	1.01 (19)	C3—C1'—C6'—O7	5.47 (18)
O3—C5—C10—C4	−0.8 (2)	C2'—C1'—C6'—C5'	5.80 (18)
C6—C5—C10—C4	178.01 (12)	C3—C1'—C6'—C5'	−177.61 (11)
O2—C4—C10—C9	178.02 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.95 (3)	1.69 (3)	2.582 (1)	155 (2)
O4—H4O···O5ⁱ	0.84 (3)	2.24 (3)	2.879 (2)	133 (2)
O4—H4O···O6ⁱ	0.84 (3)	2.33 (3)	3.071 (2)	147 (2)
C2—H2···O2ⁱⁱ	0.93 (2)	2.47 (2)	3.006 (2)	117 (1)
C11—H11A···O3ⁱⁱⁱ	1.00 (2)	2.60 (2)	3.510 (2)	151 (2)

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

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2-(5,7-Di­hydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzo­quinone (isoflavone­quinone)

Supporting information

Key indicators

checkCIF results

2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone (isoflavonequinone)