1,13-Dimethyl-6H,7H,8H-chromeno[3′,4′:5,6]pyrano[3,2-c]chromene-6,8-dione

Choudhary, M.I.; Lannang, A.M.; Anjum, S.; Fun, H.-K.; Lontsi, D.; Tangmouo, J.G.

doi:10.1107/S1600536805040523

1,13-Dimethyl-6H,7H,8H-chromeno[3′,4′:5,6]pyrano[3,2-c]chromene-6,8-dione

M. I. Choudhary, A. M. Lannang, S. Anjum, H.-K. Fun, D. Lontsi and J. G. Tangmouo

The title compound, C₂₁H₁₄O₅, is a pentacyclic chromene derivative. The dihedral angle between the two outer benzene rings is 30.3 (1)°. The pyran and one of the pyranone rings adopt twist-boat conformations. The crystal packing is stabilized by C—H

O, C—H

π and π–π interactions

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040523/ci6727sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040523/ci6727Isup2.hkl Contains datablock I

CCDC reference: 296543

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.136
Data-to-parameter ratio = 11.4

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No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion


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Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Prof. Ibqal and Dr. Shazia are supervisors of the research students, Alain Meli Lannang and David Lontsi, in this collaborative publication. HEJ is involved in the extraction and isolation of the title compound and Dr. Shazia and Prof. H. K. Fun are involved in the structure determination. All parties are involved in writing up the manuscript.


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Diospyros canaliculata De Wildeman (Ebenaceae) is a tree up to 15–20 m tall (Letouzey & White, 1970) found throughout the forest zone of West and Central Africa (Jeffreys et al., 1983). The bark extract is poisonous and causes blistering and gangrene round wounds, and is a common ingredient of the Guere (Ivory Coast) arrow poisons (Irvine, 1961). Previous investigation of the stem bark of this plant led to the isolation of gerberinol, (I) (Sengupta et al., 1985; Paknikar et al., 1996; Tangmouo et al., 2005). In the present work, we have undertaken the X-ray structure determination of the title compound, (II) (Sengupta et al., 1985) derived from (I).

The bond lengths in compound (II) show normal values (Allen et al., 1987). The molecule is non-planar, with the outer benzne rings A and E forming a dihedral angle of 30.3 (1)°. The pyranone ring B is planar, with a weighted average absolute torsion angle (τ) of 4.1°. The pyran ring C and pyranone ring D are slightly puckered and adopt twist-boat conformations; the Cremer and Pople (1975) puckering parameters Q, θ and ϕ are 0.185 (2) Å, 82.6 (6)° and 157.0 (8)° for ring C and 0.182 (2) Å, 89.6 (9)° and 30.9 (8)° for the ring D. The C1—C14B—C14A [128.3 (2)°] and C13—C13A—C13B [128.30 (2)°] angles are larger than 120° as a result of steric interactions between the methyl groups at the C1 and C13 positions.

As shown in Fig 1, the C16—H16C···O3 and C15—H15C···O3 hydrogen bonds generate rings of graph-set motif S(6) (Bernstein et al., 1995). The crystal packing is stabilized by C—H···O, C—H···π and π···π interactions (Table 1). The π···π interactions involve rings A, B and E of the inversion-related molecules with Cg2···Cg2ⁱⁱ = 3.593 (3) Å, Cg1···Cg1ⁱⁱⁱ = 3.544 (3) Å and Cg3···Cg3ⁱⁱⁱ = 3.790?(4) Å [symmetry codes: (ii) 1 − x, 1 − y, 1 − z; (iii) 1 − x, 2 − y, 1 − z; (iii) 1 − x, 1 − y, −z], where Cg1, Cg2 and Cg3 are the centroids of rings A, B and E, respectively. The C—H···π interaction involves ring A. A view of the molecular packing is shown in Fig. 2.

Experimental top

Compound (II) was prepared from gerberinol (I) using the literature method of Sengupta et al. (1985). A solution of (I) (15 mg) in pyridine (0.5 ml) and acetic anhydride (0.5 ml) was stirred for 2 d at room temperature. The solvent was evaporated and the pink solid residue obtained was crystallized from CHCl₃—CH₃OH (1:1 v/v) to afford compound (II) as pink shiny crystals (yield 54%, 8 mg; m.p. 523 K).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek,2003).

Figures top

	Fig. 1. The molecular structure of (II), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of (II), viewed approximately along the b axis. Dashed lines indicate hydrogen bonds.

1,13-Dimethyl-6H,7H,8H-chromeno[3',4':5,6]pyrano[3,2-c]chromene-6,8-dione top

Crystal data top

C₂₁H₁₄O₅	Z = 2
M_r = 346.32	F(000) = 360
Triclinic, P1	D_x = 1.495 Mg m⁻³
Hall symbol: -P 1	Melting point: 523 K
a = 8.052 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.492 (7) Å	Cell parameters from 3408 reflections
c = 12.544 (10) Å	θ = 1.7–25.0°
α = 91.441 (13)°	µ = 0.11 mm⁻¹
β = 106.324 (13)°	T = 293 K
γ = 109.489 (13)°	Plate, pink
V = 769.2 (11) Å³	0.24 × 0.12 × 0.06 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2695 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
T_min = 0.975, T_max = 0.994	l = −14→14
6917 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0615P)² + 0.1079P] where P = (F_o² + 2F_c²)/3
2695 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₁H₁₄O₅	γ = 109.489 (13)°
M_r = 346.32	V = 769.2 (11) Å³
Triclinic, P1	Z = 2
a = 8.052 (6) Å	Mo Kα radiation
b = 8.492 (7) Å	µ = 0.11 mm⁻¹
c = 12.544 (10) Å	T = 293 K
α = 91.441 (13)°	0.24 × 0.12 × 0.06 mm
β = 106.324 (13)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2695 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1842 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.994	R_int = 0.036
6917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2695 reflections	Δρ_min = −0.19 e Å⁻³
237 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	0.1354 (2)	0.4001 (2)	0.56953 (14)	0.0475 (5)
O2	−0.0884 (2)	0.0929 (2)	0.16540 (14)	0.0487 (5)
O3	0.3509 (2)	0.64825 (19)	0.27737 (12)	0.0330 (4)
O5	0.3737 (2)	0.6397 (2)	0.61133 (13)	0.0416 (5)
O9	0.0746 (2)	0.2120 (2)	0.05512 (14)	0.0440 (5)
C1	0.6665 (3)	0.8971 (3)	0.4530 (2)	0.0342 (6)
C2	0.7895 (3)	1.0164 (3)	0.5423 (2)	0.0430 (7)
H2A	0.8865	1.1031	0.5300	0.052*
C3	0.7740 (4)	1.0117 (3)	0.6490 (2)	0.0456 (7)
H3A	0.8578	1.0954	0.7068	0.055*
C4	0.6341 (3)	0.8828 (3)	0.6696 (2)	0.0421 (7)
H4A	0.6247	0.8758	0.7417	0.051*
C4A	0.5082 (3)	0.7643 (3)	0.58161 (19)	0.0344 (6)
C6	0.2413 (3)	0.5077 (3)	0.5350 (2)	0.0345 (6)
C6A	0.2368 (3)	0.5110 (3)	0.41913 (18)	0.0303 (5)
C7	0.0860 (3)	0.3698 (3)	0.33816 (19)	0.0370 (6)
H7A	0.0828	0.2632	0.3654	0.044*
H7B	−0.0325	0.3813	0.3308	0.044*
C7A	0.1192 (3)	0.3724 (3)	0.22766 (19)	0.0309 (6)
C8	0.0241 (3)	0.2192 (3)	0.1501 (2)	0.0354 (6)
C9A	0.1727 (3)	0.3576 (3)	0.02015 (19)	0.0361 (6)
C10	0.1884 (4)	0.3338 (4)	−0.0858 (2)	0.0444 (7)
H10A	0.1445	0.2264	−0.1252	0.053*
C11	0.2709 (4)	0.4737 (4)	−0.1307 (2)	0.0500 (8)
H11A	0.2867	0.4616	−0.2007	0.060*
C12	0.3304 (3)	0.6325 (4)	−0.0721 (2)	0.0468 (7)
H12A	0.3793	0.7256	−0.1061	0.056*
C13	0.3206 (3)	0.6596 (3)	0.03507 (19)	0.0376 (6)
C13A	0.2475 (3)	0.5150 (3)	0.08589 (18)	0.0321 (6)
C13B	0.2344 (3)	0.5091 (3)	0.19941 (18)	0.0298 (5)
C14A	0.3626 (3)	0.6365 (3)	0.38912 (18)	0.0282 (5)
C14B	0.5143 (3)	0.7679 (3)	0.47108 (18)	0.0307 (6)
C15	0.7035 (3)	0.9121 (3)	0.3421 (2)	0.0461 (7)
H15A	0.8312	0.9790	0.3539	0.069*
H15B	0.6261	0.9650	0.2960	0.069*
H15C	0.6769	0.8019	0.3055	0.069*
C16	0.3758 (4)	0.8381 (3)	0.0864 (2)	0.0484 (7)
H16A	0.3331	0.9022	0.0301	0.073*
H16B	0.5082	0.8865	0.1167	0.073*
H16C	0.3214	0.8397	0.1452	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0598 (12)	0.0468 (12)	0.0397 (11)	0.0125 (10)	0.0280 (9)	0.0132 (9)
O2	0.0521 (11)	0.0330 (11)	0.0440 (11)	−0.0039 (9)	0.0123 (9)	0.0027 (9)
O3	0.0369 (9)	0.0298 (10)	0.0241 (8)	0.0019 (8)	0.0092 (7)	0.0019 (7)
O5	0.0482 (11)	0.0465 (11)	0.0267 (9)	0.0111 (9)	0.0132 (8)	0.0021 (8)
O9	0.0567 (12)	0.0344 (11)	0.0353 (10)	0.0086 (9)	0.0152 (9)	−0.0014 (8)
C1	0.0321 (13)	0.0306 (14)	0.0380 (14)	0.0127 (11)	0.0058 (11)	0.0054 (12)
C2	0.0340 (14)	0.0326 (15)	0.0503 (17)	0.0066 (12)	0.0013 (12)	0.0017 (13)
C3	0.0416 (15)	0.0406 (17)	0.0426 (16)	0.0148 (13)	−0.0041 (13)	−0.0084 (13)
C4	0.0474 (16)	0.0485 (18)	0.0303 (14)	0.0237 (14)	0.0044 (12)	−0.0042 (13)
C4A	0.0348 (13)	0.0365 (15)	0.0313 (13)	0.0148 (12)	0.0067 (11)	0.0035 (11)
C6	0.0421 (14)	0.0358 (15)	0.0321 (14)	0.0174 (12)	0.0168 (12)	0.0053 (12)
C6A	0.0344 (13)	0.0295 (14)	0.0289 (13)	0.0118 (11)	0.0122 (10)	0.0042 (11)
C7	0.0406 (14)	0.0338 (15)	0.0352 (14)	0.0062 (12)	0.0181 (11)	0.0053 (11)
C7A	0.0325 (13)	0.0288 (14)	0.0295 (13)	0.0079 (11)	0.0105 (10)	0.0039 (11)
C8	0.0374 (14)	0.0341 (15)	0.0294 (13)	0.0085 (12)	0.0073 (11)	0.0037 (11)
C9A	0.0384 (14)	0.0371 (15)	0.0308 (13)	0.0111 (12)	0.0102 (11)	0.0041 (12)
C10	0.0508 (16)	0.0505 (18)	0.0299 (14)	0.0185 (14)	0.0096 (12)	−0.0049 (13)
C11	0.0568 (18)	0.069 (2)	0.0276 (14)	0.0235 (16)	0.0170 (13)	0.0047 (15)
C12	0.0462 (16)	0.059 (2)	0.0323 (15)	0.0114 (14)	0.0154 (12)	0.0143 (14)
C13	0.0355 (13)	0.0444 (16)	0.0294 (13)	0.0108 (12)	0.0085 (11)	0.0098 (12)
C13A	0.0313 (12)	0.0378 (15)	0.0253 (12)	0.0106 (11)	0.0077 (10)	0.0038 (11)
C13B	0.0305 (12)	0.0288 (14)	0.0268 (12)	0.0087 (11)	0.0060 (10)	0.0016 (11)
C14A	0.0361 (13)	0.0304 (14)	0.0239 (12)	0.0164 (11)	0.0122 (10)	0.0040 (10)
C14B	0.0318 (13)	0.0297 (14)	0.0303 (13)	0.0122 (11)	0.0075 (10)	0.0042 (11)
C15	0.0351 (14)	0.0492 (18)	0.0450 (16)	0.0029 (13)	0.0126 (12)	0.0126 (13)
C16	0.0618 (18)	0.0372 (16)	0.0372 (15)	0.0067 (14)	0.0140 (13)	0.0129 (13)

Geometric parameters (Å, º) top

O1—C6	1.207 (3)	C7—H7A	0.97
O2—C8	1.211 (3)	C7—H7B	0.97
O3—C13B	1.386 (3)	C7A—C13B	1.349 (3)
O3—C14A	1.387 (3)	C7A—C8	1.442 (3)
O5—C6	1.373 (3)	C9A—C10	1.386 (3)
O5—C4A	1.383 (3)	C9A—C13A	1.399 (4)
O9—C8	1.369 (3)	C10—C11	1.374 (4)
O9—C9A	1.384 (3)	C10—H10A	0.93
C1—C2	1.383 (3)	C11—C12	1.382 (4)
C1—C14B	1.425 (3)	C11—H11A	0.93
C1—C15	1.502 (4)	C12—C13	1.386 (4)
C2—C3	1.380 (4)	C12—H12A	0.93
C2—H2A	0.93	C13—C13A	1.424 (3)
C3—C4	1.374 (4)	C13—C16	1.500 (4)
C3—H3A	0.93	C13A—C13B	1.458 (3)
C4—C4A	1.376 (3)	C14A—C14B	1.457 (3)
C4—H4A	0.93	C15—H15A	0.96
C4A—C14B	1.402 (3)	C15—H15B	0.96
C6—C6A	1.445 (3)	C15—H15C	0.96
C6A—C14A	1.348 (3)	C16—H16A	0.96
C6A—C7	1.489 (3)	C16—H16B	0.96
C7—C7A	1.483 (3)	C16—H16C	0.96

C13B—O3—C14A	117.94 (18)	C10—C9A—C13A	123.2 (2)
C6—O5—C4A	122.07 (19)	C11—C10—C9A	117.9 (3)
C8—O9—C9A	120.7 (2)	C11—C10—H10A	121.0
C2—C1—C14B	118.7 (2)	C9A—C10—H10A	121.0
C2—C1—C15	117.3 (2)	C10—C11—C12	120.1 (3)
C14B—C1—C15	124.0 (2)	C10—C11—H11A	119.9
C3—C2—C1	122.5 (3)	C12—C11—H11A	119.9
C3—C2—H2A	118.8	C11—C12—C13	123.0 (3)
C1—C2—H2A	118.8	C11—C12—H12A	118.5
C4—C3—C2	119.7 (2)	C13—C12—H12A	118.5
C4—C3—H3A	120.1	C12—C13—C13A	117.4 (3)
C2—C3—H3A	120.1	C12—C13—C16	118.0 (2)
C3—C4—C4A	118.8 (2)	C13A—C13—C16	124.5 (2)
C3—C4—H4A	120.6	C9A—C13A—C13	117.7 (2)
C4A—C4—H4A	120.6	C9A—C13A—C13B	114.3 (2)
C4—C4A—O5	114.2 (2)	C13—C13A—C13B	128.0 (2)
C4—C4A—C14B	123.4 (2)	C7A—C13B—O3	121.9 (2)
O5—C4A—C14B	122.4 (2)	C7A—C13B—C13A	121.5 (2)
O1—C6—O5	117.5 (2)	O3—C13B—C13A	116.6 (2)
O1—C6—C6A	125.2 (2)	C6A—C14A—O3	121.1 (2)
O5—C6—C6A	117.3 (2)	C6A—C14A—C14B	122.2 (2)
C14A—C6A—C6	120.6 (2)	O3—C14A—C14B	116.6 (2)
C14A—C6A—C7	123.6 (2)	C4A—C14B—C1	116.7 (2)
C6—C6A—C7	115.7 (2)	C4A—C14B—C14A	115.0 (2)
C7A—C7—C6A	109.4 (2)	C1—C14B—C14A	128.3 (2)
C7A—C7—H7A	109.8	C1—C15—H15A	109.5
C6A—C7—H7A	109.8	C1—C15—H15B	109.5
C7A—C7—H7B	109.8	H15A—C15—H15B	109.5
C6A—C7—H7B	109.8	C1—C15—H15C	109.5
H7A—C7—H7B	108.2	H15A—C15—H15C	109.5
C13B—C7A—C8	120.3 (2)	H15B—C15—H15C	109.5
C13B—C7A—C7	122.8 (2)	C13—C16—H16A	109.5
C8—C7A—C7	116.9 (2)	C13—C16—H16B	109.5
O2—C8—O9	117.3 (2)	H16A—C16—H16B	109.5
O2—C8—C7A	125.3 (2)	C13—C16—H16C	109.5
O9—C8—C7A	117.2 (2)	H16A—C16—H16C	109.5
O9—C9A—C10	114.1 (2)	H16B—C16—H16C	109.5
O9—C9A—C13A	122.7 (2)

C14B—C1—C2—C3	2.2 (4)	O9—C9A—C13A—C13B	7.6 (3)
C15—C1—C2—C3	−177.4 (2)	C10—C9A—C13A—C13B	−173.1 (2)
C1—C2—C3—C4	1.4 (4)	C12—C13—C13A—C9A	−6.7 (3)
C2—C3—C4—C4A	−2.4 (4)	C16—C13—C13A—C9A	169.1 (2)
C3—C4—C4A—O5	179.7 (2)	C12—C13—C13A—C13B	175.4 (2)
C3—C4—C4A—C14B	−0.2 (4)	C16—C13—C13A—C13B	−8.8 (4)
C6—O5—C4A—C4	−177.4 (2)	C8—C7A—C13B—O3	−169.1 (2)
C6—O5—C4A—C14B	2.4 (3)	C7—C7A—C13B—O3	9.8 (3)
C4A—O5—C6—O1	176.2 (2)	C8—C7A—C13B—C13A	8.5 (3)
C4A—O5—C6—C6A	−5.3 (3)	C7—C7A—C13B—C13A	−172.5 (2)
O1—C6—C6A—C14A	−179.5 (2)	C14A—O3—C13B—C7A	7.5 (3)
O5—C6—C6A—C14A	2.2 (3)	C14A—O3—C13B—C13A	−170.32 (18)
O1—C6—C6A—C7	1.0 (3)	C9A—C13A—C13B—C7A	−16.3 (3)
O5—C6—C6A—C7	−177.3 (2)	C13—C13A—C13B—C7A	161.6 (2)
C14A—C6A—C7—C7A	10.8 (3)	C9A—C13A—C13B—O3	161.5 (2)
C6—C6A—C7—C7A	−169.7 (2)	C13—C13A—C13B—O3	−20.6 (3)
C6A—C7—C7A—C13B	−17.9 (3)	C6—C6A—C14A—O3	−174.85 (19)
C6A—C7—C7A—C8	161.1 (2)	C7—C6A—C14A—O3	4.7 (3)
C9A—O9—C8—O2	167.2 (2)	C6—C6A—C14A—C14B	3.8 (3)
C9A—O9—C8—C7A	−17.3 (3)	C7—C6A—C14A—C14B	−176.7 (2)
C13B—C7A—C8—O2	−176.3 (2)	C13B—O3—C14A—C6A	−14.6 (3)
C7—C7A—C8—O2	4.7 (4)	C13B—O3—C14A—C14B	166.67 (19)
C13B—C7A—C8—O9	8.6 (3)	C4—C4A—C14B—C1	3.6 (3)
C7—C7A—C8—O9	−170.4 (2)	O5—C4A—C14B—C1	−176.2 (2)
C8—O9—C9A—C10	−170.3 (2)	C4—C4A—C14B—C14A	−176.7 (2)
C8—O9—C9A—C13A	9.1 (3)	O5—C4A—C14B—C14A	3.4 (3)
O9—C9A—C10—C11	174.9 (2)	C2—C1—C14B—C4A	−4.5 (3)
C13A—C9A—C10—C11	−4.5 (4)	C15—C1—C14B—C4A	175.1 (2)
C9A—C10—C11—C12	−1.9 (4)	C2—C1—C14B—C14A	175.9 (2)
C10—C11—C12—C13	3.6 (4)	C15—C1—C14B—C14A	−4.5 (4)
C11—C12—C13—C13A	0.8 (4)	C6A—C14A—C14B—C4A	−6.5 (3)
C11—C12—C13—C16	−175.3 (2)	O3—C14A—C14B—C4A	172.18 (19)
O9—C9A—C13A—C13	−170.6 (2)	C6A—C14A—C14B—C1	173.1 (2)
C10—C9A—C13A—C13	8.8 (4)	O3—C14A—C14B—C1	−8.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.57	3.442 (4)	155
C15—H15C···O3	0.96	2.43	2.848 (4)	106
C16—H16C···O3	0.96	2.37	2.937 (4)	117
C7—H7A···Cg1ⁱⁱ	0.97	2.84	3.583 (4)	134

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄O₅
M_r	346.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.052 (6), 8.492 (7), 12.544 (10)
α, β, γ (°)	91.441 (13), 106.324 (13), 109.489 (13)
V (Å³)	769.2 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.12 × 0.06

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	6917, 2695, 1842
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.136, 1.05
No. of reflections	2695
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek,2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.57	3.442 (4)	155
C15—H15C···O3	0.96	2.43	2.848 (4)	106
C16—H16C···O3	0.96	2.37	2.937 (4)	117
C7—H7A···Cg1ⁱⁱ	0.97	2.84	3.583 (4)	134

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

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