Isoderrone

The title compound, C₂₀H₁₆O₅, also known as 5,7-dihyr­oxy-3-(2′,2′-dimethyl-2H'-chromen-7′-yl)chroman-4-one, was isolated from the medicinal plant Ficus mucuso. The benzopyran­one (chromen-4-one) ring system is essentially planar and the dihedral angle between the benzopyranone ring system and the other benzene ring is 37.7 (10)°. In the crystal structure, one-dimensional chains are formed via inter­molecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 220 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.117
• Data-to-parameter ratio = 16.1

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Author Response: Identification and collection of plant, fractionation of extract and isolation were made at the Departement of Organic Chemistry, Faculty of Science, UY1, Cameroon by Jean Jules Bankeu , Bruno Ndjakou Lenta, Silvere Ngouela and Etienne Tsamo. Crystallisation, NMR , Xray analysis , interpretation of data were carried on at Bielefed University by Bruno Ndjakou Lenta, Norbert Sewald, Beate Newmann and Hans-Georg Stammler

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97.

5,7-dihyroxy-3-(2',2'-dimethyl-2H'-chromen-7'-yl)chroman-4-one

Crystal data

C20H16O5	F(000) = 704
Mr = 336.33	Dx = 1.389 Mg m^−3
Monoclinic, P21/c	Melting point: 215 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9241 (2) Å	Cell parameters from 25785 reflections
b = 12.4116 (3) Å	θ = 2.9–27.5°
c = 16.4595 (3) Å	µ = 0.10 mm^−1
β = 96.5733 (13)°	T = 220 K
V = 1608.15 (6) Å^3	Rhomb, yellow
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ scans and ω	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.971, Tmax = 0.971	k = −16→16
38284 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0674P)^2 + 0.2171P] where P = (Fo^2 + 2Fc^2)/3
3678 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.09628 (14)	0.61604 (8)	0.43722 (5)	0.0516 (3)
H1	−0.0599	0.6458	0.4809	0.077*
O2	−0.07379 (12)	0.64340 (8)	0.15524 (5)	0.0445 (2)
H2	−0.0335	0.6802	0.1200	0.067*
O3	0.22442 (11)	0.90051 (7)	0.32948 (5)	0.0350 (2)
O4	0.06138 (11)	0.76088 (7)	0.53152 (5)	0.0389 (2)
O5	0.44099 (12)	1.10827 (7)	0.77422 (5)	0.0383 (2)
C1	−0.03700 (15)	0.66831 (10)	0.37441 (7)	0.0338 (3)
C2	−0.08269 (15)	0.63165 (11)	0.29626 (7)	0.0358 (3)
H2A	−0.1537	0.5711	0.2873	0.043*
C3	−0.02351 (15)	0.68438 (10)	0.23029 (7)	0.0335 (3)
C4	0.08009 (15)	0.77448 (10)	0.24153 (7)	0.0331 (3)
H4	0.1194	0.8098	0.1968	0.040*
C5	0.12369 (14)	0.81064 (9)	0.32038 (7)	0.0293 (2)
C6	0.26833 (15)	0.94055 (10)	0.40499 (7)	0.0338 (3)
H6	0.3388	1.0017	0.4094	0.041*
C7	0.21974 (15)	0.90041 (9)	0.47490 (7)	0.0303 (3)
C8	0.11440 (14)	0.80424 (9)	0.46959 (6)	0.0302 (3)
C9	0.06967 (14)	0.76025 (9)	0.38919 (6)	0.0292 (2)
C10	0.27451 (14)	0.95483 (10)	0.55400 (7)	0.0308 (3)
C11	0.27728 (15)	1.06718 (10)	0.56043 (7)	0.0344 (3)
H11	0.2421	1.1092	0.5141	0.041*
C12	0.33114 (16)	1.11768 (10)	0.63426 (7)	0.0352 (3)
H12	0.3330	1.1933	0.6374	0.042*
C13	0.38219 (15)	1.05661 (10)	0.70334 (7)	0.0315 (3)
C14	0.42977 (17)	1.05071 (10)	0.85129 (7)	0.0370 (3)
C15	0.47297 (17)	0.93358 (10)	0.84277 (7)	0.0380 (3)
H15	0.5195	0.8950	0.8891	0.046*
C16	0.44690 (16)	0.88362 (10)	0.77126 (7)	0.0364 (3)
H16	0.4695	0.8095	0.7677	0.044*
C17	0.38309 (14)	0.94398 (9)	0.69835 (7)	0.0308 (3)
C18	0.32896 (15)	0.89531 (9)	0.62398 (7)	0.0315 (3)
H18	0.3290	0.8197	0.6207	0.038*
C19	0.5572 (2)	1.10677 (13)	0.91300 (8)	0.0556 (4)
H19A	0.6691	1.1034	0.8946	0.083*
H19B	0.5596	1.0713	0.9656	0.083*
H19C	0.5244	1.1815	0.9182	0.083*
C20	0.2494 (2)	1.06373 (12)	0.87295 (9)	0.0510 (4)
H20A	0.2250	1.1396	0.8793	0.077*
H20B	0.2381	1.0263	0.9238	0.077*
H20C	0.1702	1.0336	0.8296	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0690 (7)	0.0605 (6)	0.0266 (5)	−0.0275 (5)	0.0113 (4)	−0.0004 (4)
O2	0.0543 (6)	0.0564 (6)	0.0232 (4)	−0.0157 (5)	0.0060 (4)	−0.0077 (4)
O3	0.0440 (5)	0.0391 (5)	0.0223 (4)	−0.0070 (4)	0.0056 (3)	−0.0006 (3)
O4	0.0489 (5)	0.0462 (5)	0.0221 (4)	−0.0064 (4)	0.0072 (4)	0.0004 (3)
O5	0.0569 (6)	0.0335 (5)	0.0237 (4)	−0.0070 (4)	0.0015 (4)	−0.0013 (3)
C1	0.0377 (6)	0.0390 (6)	0.0257 (5)	−0.0026 (5)	0.0073 (5)	0.0010 (5)
C2	0.0383 (6)	0.0406 (7)	0.0289 (6)	−0.0058 (5)	0.0058 (5)	−0.0033 (5)
C3	0.0350 (6)	0.0427 (7)	0.0227 (5)	0.0015 (5)	0.0032 (4)	−0.0039 (5)
C4	0.0369 (6)	0.0415 (6)	0.0216 (5)	−0.0014 (5)	0.0062 (4)	0.0002 (5)
C5	0.0297 (5)	0.0332 (6)	0.0254 (5)	0.0023 (4)	0.0045 (4)	0.0007 (4)
C6	0.0369 (6)	0.0361 (6)	0.0280 (6)	−0.0009 (5)	0.0019 (5)	−0.0027 (5)
C7	0.0328 (6)	0.0341 (6)	0.0236 (5)	0.0050 (4)	0.0014 (4)	−0.0011 (4)
C8	0.0319 (6)	0.0371 (6)	0.0220 (5)	0.0045 (5)	0.0041 (4)	0.0004 (4)
C9	0.0304 (5)	0.0350 (6)	0.0222 (5)	0.0027 (5)	0.0037 (4)	0.0001 (4)
C10	0.0316 (6)	0.0354 (6)	0.0251 (5)	0.0027 (5)	0.0024 (4)	−0.0017 (4)
C11	0.0391 (6)	0.0359 (6)	0.0274 (6)	0.0056 (5)	0.0002 (5)	0.0031 (5)
C12	0.0453 (7)	0.0286 (6)	0.0310 (6)	0.0034 (5)	0.0014 (5)	0.0005 (5)
C13	0.0356 (6)	0.0340 (6)	0.0246 (5)	−0.0002 (5)	0.0027 (4)	−0.0029 (4)
C14	0.0511 (7)	0.0375 (6)	0.0219 (5)	−0.0065 (5)	0.0022 (5)	−0.0002 (5)
C15	0.0458 (7)	0.0400 (7)	0.0266 (6)	0.0008 (5)	−0.0022 (5)	0.0053 (5)
C16	0.0448 (7)	0.0328 (6)	0.0305 (6)	0.0039 (5)	−0.0010 (5)	0.0030 (5)
C17	0.0334 (6)	0.0329 (6)	0.0258 (6)	0.0027 (5)	0.0021 (4)	0.0004 (4)
C18	0.0370 (6)	0.0290 (6)	0.0280 (6)	0.0034 (4)	0.0012 (5)	−0.0015 (4)
C19	0.0817 (11)	0.0537 (9)	0.0290 (7)	−0.0267 (8)	−0.0047 (7)	0.0010 (6)
C20	0.0596 (9)	0.0501 (8)	0.0455 (8)	0.0031 (7)	0.0158 (7)	−0.0008 (6)

Geometric parameters (Å, º)

O1—C1	1.3496 (14)	C10—C18	1.3946 (16)
O1—H1	0.83	C10—C11	1.3984 (17)
O2—C3	1.3530 (13)	C11—C12	1.3902 (16)
O2—H2	0.83	C11—H11	0.94
O3—C6	1.3468 (13)	C12—C13	1.3876 (16)
O3—C5	1.3698 (14)	C12—H12	0.94
O4—C8	1.2661 (13)	C13—C17	1.4004 (17)
O5—C13	1.3655 (13)	C14—C15	1.5039 (18)
O5—C14	1.4675 (14)	C14—C19	1.5166 (18)
C1—C2	1.3733 (16)	C14—C20	1.520 (2)
C1—C9	1.4244 (17)	C15—C16	1.3255 (17)
C2—C3	1.3942 (16)	C15—H15	0.9400
C2—H2A	0.94	C16—C17	1.4554 (16)
C3—C4	1.3871 (17)	C16—H16	0.9400
C4—C5	1.3793 (15)	C17—C18	1.3882 (15)
C4—H4	0.94	C18—H18	0.94
C5—C9	1.4029 (15)	C19—H19A	0.97
C6—C7	1.3498 (16)	C19—H19B	0.97
C6—H6	0.94	C19—H19C	0.97
C7—C8	1.4535 (17)	C20—H20A	0.97
C7—C10	1.4867 (15)	C20—H20B	0.97
C8—C9	1.4379 (15)	C20—H20C	0.97
C1—O1—H1	109.5	C13—C12—C11	120.10 (11)
C3—O2—H2	109.5	C13—C12—H12	120.0
C6—O3—C5	119.15 (9)	C11—C12—H12	120.0
C13—O5—C14	117.48 (9)	O5—C13—C12	118.85 (11)
O1—C1—C2	118.73 (11)	O5—C13—C17	121.02 (10)
O1—C1—C9	120.40 (10)	C12—C13—C17	120.01 (10)
C2—C1—C9	120.86 (10)	O5—C14—C15	110.67 (9)
C1—C2—C3	119.86 (11)	O5—C14—C19	104.71 (10)
C1—C2—H2A	120.1	C15—C14—C19	111.39 (12)
C3—C2—H2A	120.1	O5—C14—C20	107.61 (11)
O2—C3—C4	122.20 (10)	C15—C14—C20	110.78 (11)
O2—C3—C2	116.38 (11)	C19—C14—C20	111.46 (12)
C4—C3—C2	121.42 (10)	C16—C15—C14	121.41 (11)
C5—C4—C3	117.94 (10)	C16—C15—H15	119.3
C5—C4—H4	121.0	C14—C15—H15	119.3
C3—C4—H4	121.0	C15—C16—C17	119.70 (12)
O3—C5—C4	116.61 (10)	C15—C16—H16	120.2
O3—C5—C9	120.18 (10)	C17—C16—H16	120.2
C4—C5—C9	123.21 (11)	C18—C17—C13	118.88 (10)
O3—C6—C7	125.57 (11)	C18—C17—C16	123.10 (11)
O3—C6—H6	117.2	C13—C17—C16	117.98 (10)
C7—C6—H6	117.2	C17—C18—C10	122.20 (11)
C6—C7—C8	118.02 (10)	C17—C18—H18	118.9
C6—C7—C10	119.71 (11)	C10—C18—H18	118.9
C8—C7—C10	122.27 (10)	C14—C19—H19A	109.5
O4—C8—C9	120.66 (11)	C14—C19—H19B	109.5
O4—C8—C7	122.81 (10)	H19A—C19—H19B	109.5
C9—C8—C7	116.52 (10)	C14—C19—H19C	109.5
C5—C9—C1	116.70 (10)	H19A—C19—H19C	109.5
C5—C9—C8	120.52 (11)	H19B—C19—H19C	109.5
C1—C9—C8	122.70 (10)	C14—C20—H20A	109.5
C18—C10—C11	117.71 (10)	C14—C20—H20B	109.5
C18—C10—C7	120.95 (11)	H20A—C20—H20B	109.5
C11—C10—C7	121.32 (10)	C14—C20—H20C	109.5
C12—C11—C10	121.09 (11)	H20A—C20—H20C	109.5
C12—C11—H11	119.5	H20B—C20—H20C	109.5
C10—C11—H11	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.83	1.86	2.5995 (15)	147
O2—H2···O4^i	0.83	1.86	2.6842 (16)	170

Symmetry code: (i) x, −y+3/2, z−1/2.