3-Acetyl-5-hy­droxy-2-methyl­anthra[1,2-b]furan-6,11-dione

Ahmad, R.; Jeinie, M.F.; Ismail, N.H.; Hazni, H.; Ng, S.W.

doi:10.1107/S1600536811013389

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1144

doi:10.1107/S1600536811013389

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3-Acetyl-5-hydroxy-2-methylanthra[1,2-b]furan-6,11-dione

Rohaya Ahmad,^a Mohamad Faiz Jeinie,^a Nor Hadiani Ismail,^a Hazrina Hazni ^b and Seik Weng Ng ^b ^*

^aFaculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam 40450, Selangor, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 April 2011; accepted 10 April 2011; online 16 April 2011)

The asymmetric unit of the title compound, C₁₉H₁₂O₅, contains two independent molecules, both slightly buckled along an axis passing through the C=O bonds of the anthraquinone ring system (r.m.s. deviation of non-H atoms = 0.082 and 0.148 Å): the benzene rings are twisted to each other by 4.3 (3)°in one molecule and 10.6(3)° in the other. In both molecules, the hydroxy group forms an intramolecular O—H⋯O hydrogen bond. The two independent molecules interact by π–π stacking with a centroid–centroid distance of 3.539 (2) Å between hydroxybenzene rings of adjacent molecules.

Related literature

For background to the synthesis, see: Boddy et al. (1986 ).

Experimental

Crystal data

C₁₉H₁₂O₅
M_r = 320.29
Monoclinic, P 2₁ /c
a = 12.5739 (9) Å
b = 22.0375 (12) Å
c = 10.7453 (8) Å
β = 110.342 (8)°
V = 2791.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.35 × 0.05 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.962, T_max = 0.998
12061 measured reflections
4905 independent reflections
2305 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.149
S = 0.95
4905 reflections
445 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4	0.84 (1)	1.82 (2)	2.596 (4)	153 (4)
O10—H10⋯O9	0.84 (1)	1.77 (3)	2.552 (4)	153 (6)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013389/xu5188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013389/xu5188Isup2.hkl

checkCIF report

Comment top

The title compound (Scheme I) is one of the intermediates of the multi-stepsynthesis of a substituted isobenzofuran from anthradifuran (Boddy et al., 1986). In the present microwave-assisted synthesis, even the 1,4-dihdyroanthraquinone reactant can be prepared under microwave conditions.

The two independent molecules C₁₉H₁₂O₅ (Fig. 1 and Fig. 2) are both slightly buckled along an axis passing through the C═O bonds of the anthraquinone ring-system; for one molecule, the benzene rings are twisted by 4.3 (3) ° and for the other, the benzene rings are twisted by 10.6 (3)°. The two independent molecules interact by π–π stacking with a centroid-to-centroid distance of 3.539 (2) Å between hydroxybenzene rings of adjacent molecules.

Related literature top

For background to the synthesis, see: Boddy et al. (1986).

Experimental top

Phthalic anhydride (0.001 mol) and hydroquinone (0.001 mol) were reacted over montmorillonite K10 clay (without any solvent) in a microwave oven. The reactants were subject to microwave radiation for 1 h. This afforded 1,4-dihydroxyanthraquinone in 95% yield. In the next step, acetylacetone (0.001 mol) was added to the prepared 1,4-dihydroxyanthraquinone (0.001 mol) in the presence of 4-dimethylaminopyridine (0.01 mol). The mixture was agained subject to microwave irradiation (100% power level for 1 h) to give the title compound, whose formulation was established by 1H NMR spectroscopy; yield 95% yield. Orange crystals were obtained by recrystallization from a hexane-chloroform (5:95) mixture.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of one independent molecule of C₁₉H₁₂O₅ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of second independent molecule of C₁₉H₁₂O₅ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 3. π–π Stacking of the two independent molecules of C₁₉H₁₂O₅.

3-Acetyl-5-hydroxy-2-methylanthra[1,2-b]furan-6,11-dione top

Crystal data top

C₁₉H₁₂O₅	F(000) = 1328
M_r = 320.29	D_x = 1.524 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1530 reflections
a = 12.5739 (9) Å	θ = 2.2–29.1°
b = 22.0375 (12) Å	µ = 0.11 mm⁻¹
c = 10.7453 (8) Å	T = 100 K
β = 110.342 (8)°	Plate, orange
V = 2791.8 (3) Å³	0.35 × 0.05 × 0.02 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4905 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2305 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.093
Detector resolution: 10.4041 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −26→21
T_min = 0.962, T_max = 0.998	l = −12→9
12061 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.029P)²] where P = (F_o² + 2F_c²)/3
4905 reflections	(Δ/σ)_max = 0.001
445 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₂O₅	V = 2791.8 (3) Å³
M_r = 320.29	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5739 (9) Å	µ = 0.11 mm⁻¹
b = 22.0375 (12) Å	T = 100 K
c = 10.7453 (8) Å	0.35 × 0.05 × 0.02 mm
β = 110.342 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4905 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2305 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.998	R_int = 0.093
12061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	2 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.25 e Å⁻³
4905 reflections	Δρ_min = −0.28 e Å⁻³
445 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.1639 (2)	0.63359 (13)	0.4656 (3)	0.0307 (8)
O2	0.1956 (2)	0.42672 (12)	0.4828 (3)	0.0225 (7)
O3	0.1802 (2)	0.32131 (13)	0.6137 (3)	0.0308 (8)
O4	0.0110 (2)	0.44812 (14)	0.9299 (3)	0.0406 (9)
O5	0.0397 (3)	0.55000 (14)	0.8246 (3)	0.0303 (8)
O6	0.4668 (2)	0.26821 (13)	0.8213 (3)	0.0361 (8)
O7	0.3238 (2)	0.41683 (13)	1.0149 (3)	0.0256 (7)
O8	0.2983 (2)	0.53832 (13)	1.0463 (3)	0.0315 (8)
O9	0.4542 (2)	0.58374 (13)	0.6465 (3)	0.0297 (8)
O10	0.4846 (3)	0.47096 (16)	0.6165 (3)	0.0313 (8)
C1	0.2569 (4)	0.60289 (19)	0.3177 (5)	0.0344 (13)
H1A	0.2554	0.6464	0.2986	0.052*
H1B	0.2167	0.5807	0.2358	0.052*
H1C	0.3357	0.5889	0.3537	0.052*
C2	0.2001 (3)	0.5916 (2)	0.4175 (4)	0.0242 (11)
C3	0.1909 (3)	0.52918 (19)	0.4607 (4)	0.0218 (11)
C4	0.2152 (3)	0.4754 (2)	0.4141 (4)	0.0235 (11)
C5	0.2569 (3)	0.4558 (2)	0.3062 (4)	0.0291 (11)
H5A	0.3127	0.4232	0.3390	0.044*
H5B	0.2925	0.4904	0.2784	0.044*
H5C	0.1930	0.4411	0.2304	0.044*
C6	0.1547 (3)	0.45001 (19)	0.5772 (4)	0.0205 (10)
C7	0.1232 (3)	0.41721 (18)	0.6675 (4)	0.0195 (10)
C8	0.1320 (3)	0.3503 (2)	0.6764 (4)	0.0249 (11)
C9	0.0804 (3)	0.31883 (19)	0.7640 (4)	0.0240 (11)
C10	0.0730 (3)	0.2559 (2)	0.7613 (4)	0.0302 (12)
H10A	0.1046	0.2333	0.7073	0.036*
C11	0.0198 (4)	0.2258 (2)	0.8367 (5)	0.0373 (13)
H11	0.0144	0.1828	0.8339	0.045*
C12	−0.0259 (4)	0.2590 (2)	0.9169 (5)	0.0370 (13)
H12	−0.0635	0.2385	0.9676	0.044*
C13	−0.0167 (3)	0.3215 (2)	0.9230 (4)	0.0302 (12)
H13	−0.0455	0.3438	0.9799	0.036*
C14	0.0356 (3)	0.3520 (2)	0.8445 (4)	0.0249 (11)
C15	0.0417 (3)	0.4196 (2)	0.8474 (4)	0.0280 (12)
C16	0.0813 (3)	0.45079 (19)	0.7526 (4)	0.0219 (10)
C17	0.0767 (3)	0.5151 (2)	0.7443 (4)	0.0223 (11)
C18	0.1098 (3)	0.54647 (19)	0.6509 (4)	0.0210 (10)
H18	0.1059	0.5895	0.6459	0.025*
C19	0.1483 (3)	0.51364 (18)	0.5662 (4)	0.0178 (10)
C20	0.3954 (4)	0.22087 (18)	0.9754 (4)	0.0335 (12)
H20A	0.4295	0.1844	0.9528	0.050*
H20B	0.3133	0.2150	0.9502	0.050*
H20C	0.4284	0.2282	1.0712	0.050*
C21	0.4183 (4)	0.2744 (2)	0.9022 (4)	0.0273 (11)
C22	0.3851 (3)	0.33562 (18)	0.9271 (4)	0.0216 (10)
C23	0.3357 (3)	0.35386 (19)	1.0167 (4)	0.0232 (11)
C24	0.2934 (4)	0.32387 (19)	1.1114 (4)	0.0331 (12)
H24A	0.2659	0.2832	1.0789	0.050*
H24B	0.2310	0.3477	1.1215	0.050*
H24C	0.3548	0.3206	1.1975	0.050*
C25	0.3663 (3)	0.43878 (19)	0.9207 (4)	0.0211 (10)
C26	0.3693 (3)	0.49820 (19)	0.8854 (4)	0.0188 (10)
C27	0.3289 (3)	0.54833 (19)	0.9518 (4)	0.0223 (10)
C28	0.3271 (3)	0.61072 (19)	0.8981 (4)	0.0223 (11)
C29	0.2850 (4)	0.65801 (19)	0.9521 (5)	0.0303 (12)
H29	0.2585	0.6506	1.0235	0.036*
C30	0.2814 (4)	0.7162 (2)	0.9015 (5)	0.0341 (12)
H30	0.2503	0.7485	0.9364	0.041*
C31	0.3238 (4)	0.7273 (2)	0.7989 (5)	0.0346 (12)
H31	0.3232	0.7673	0.7658	0.042*
C32	0.3665 (3)	0.6800 (2)	0.7460 (5)	0.0309 (12)
H32	0.3942	0.6874	0.6756	0.037*
C33	0.3689 (3)	0.62214 (19)	0.7951 (4)	0.0203 (10)
C34	0.4148 (3)	0.5720 (2)	0.7356 (4)	0.0249 (11)
C35	0.4106 (3)	0.51037 (19)	0.7802 (4)	0.0193 (10)
C36	0.4479 (3)	0.46163 (19)	0.7192 (4)	0.0216 (10)
C37	0.4450 (3)	0.4014 (2)	0.7599 (4)	0.0246 (11)
H37	0.4705	0.3692	0.7187	0.030*
C38	0.4041 (3)	0.39022 (19)	0.8614 (4)	0.0218 (11)
H5	0.022 (3)	0.5247 (15)	0.873 (4)	0.034 (15)*
H10	0.478 (5)	0.5087 (7)	0.603 (6)	0.09 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0392 (19)	0.0233 (18)	0.030 (2)	−0.0006 (15)	0.0133 (16)	−0.0033 (16)
O2	0.0276 (17)	0.0213 (17)	0.0210 (18)	0.0004 (14)	0.0117 (14)	0.0014 (14)
O3	0.0354 (19)	0.0278 (19)	0.031 (2)	−0.0003 (15)	0.0138 (16)	−0.0033 (16)
O4	0.051 (2)	0.047 (2)	0.037 (2)	0.0000 (17)	0.0321 (19)	−0.0083 (18)
O5	0.0377 (19)	0.031 (2)	0.029 (2)	−0.0037 (17)	0.0201 (17)	−0.0064 (17)
O6	0.048 (2)	0.0312 (19)	0.036 (2)	0.0053 (17)	0.0242 (18)	−0.0004 (17)
O7	0.0329 (18)	0.0278 (19)	0.0185 (18)	0.0013 (15)	0.0118 (15)	0.0035 (15)
O8	0.045 (2)	0.0299 (19)	0.024 (2)	−0.0007 (16)	0.0181 (17)	−0.0013 (16)
O9	0.0312 (18)	0.036 (2)	0.028 (2)	0.0023 (15)	0.0180 (16)	0.0068 (16)
O10	0.0380 (19)	0.037 (2)	0.027 (2)	0.0013 (18)	0.0215 (16)	0.0040 (18)
C1	0.047 (3)	0.024 (3)	0.039 (3)	0.003 (2)	0.023 (3)	0.008 (2)
C2	0.022 (2)	0.029 (3)	0.020 (3)	−0.003 (2)	0.007 (2)	0.000 (2)
C3	0.020 (2)	0.025 (3)	0.020 (3)	−0.001 (2)	0.007 (2)	−0.003 (2)
C4	0.021 (2)	0.029 (3)	0.019 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C5	0.033 (3)	0.033 (3)	0.029 (3)	−0.001 (2)	0.020 (2)	−0.001 (2)
C6	0.017 (2)	0.027 (3)	0.016 (3)	0.002 (2)	0.004 (2)	−0.004 (2)
C7	0.015 (2)	0.024 (3)	0.016 (3)	−0.002 (2)	0.0015 (19)	−0.002 (2)
C8	0.022 (2)	0.032 (3)	0.017 (3)	−0.001 (2)	0.003 (2)	0.000 (2)
C9	0.022 (2)	0.031 (3)	0.015 (3)	−0.002 (2)	0.001 (2)	0.001 (2)
C10	0.029 (3)	0.034 (3)	0.025 (3)	0.000 (2)	0.006 (2)	0.005 (2)
C11	0.042 (3)	0.036 (3)	0.029 (3)	−0.003 (3)	0.006 (3)	0.011 (3)
C12	0.036 (3)	0.046 (3)	0.028 (3)	−0.003 (3)	0.010 (2)	0.016 (3)
C13	0.029 (3)	0.044 (3)	0.020 (3)	−0.001 (2)	0.011 (2)	0.002 (2)
C14	0.020 (2)	0.033 (3)	0.019 (3)	−0.002 (2)	0.005 (2)	0.004 (2)
C15	0.025 (3)	0.039 (3)	0.024 (3)	−0.003 (2)	0.014 (2)	−0.004 (2)
C16	0.016 (2)	0.029 (3)	0.020 (3)	−0.002 (2)	0.007 (2)	0.000 (2)
C17	0.020 (2)	0.035 (3)	0.015 (3)	0.001 (2)	0.009 (2)	−0.006 (2)
C18	0.021 (2)	0.020 (2)	0.020 (3)	−0.002 (2)	0.005 (2)	−0.006 (2)
C19	0.010 (2)	0.023 (3)	0.015 (3)	−0.002 (2)	−0.0008 (19)	−0.002 (2)
C20	0.053 (3)	0.024 (3)	0.029 (3)	0.004 (2)	0.020 (3)	0.003 (2)
C21	0.031 (3)	0.025 (3)	0.023 (3)	−0.002 (2)	0.006 (2)	−0.007 (2)
C22	0.022 (2)	0.023 (3)	0.018 (3)	−0.004 (2)	0.005 (2)	0.000 (2)
C23	0.025 (2)	0.018 (3)	0.021 (3)	−0.003 (2)	0.002 (2)	−0.001 (2)
C24	0.045 (3)	0.028 (3)	0.031 (3)	−0.006 (2)	0.019 (2)	0.003 (2)
C25	0.014 (2)	0.028 (3)	0.017 (3)	0.000 (2)	0.0006 (19)	−0.005 (2)
C26	0.012 (2)	0.024 (3)	0.019 (3)	−0.003 (2)	0.0029 (19)	0.002 (2)
C27	0.023 (2)	0.029 (3)	0.013 (3)	−0.002 (2)	0.004 (2)	−0.003 (2)
C28	0.021 (2)	0.026 (3)	0.019 (3)	−0.003 (2)	0.005 (2)	0.000 (2)
C29	0.038 (3)	0.027 (3)	0.027 (3)	−0.001 (2)	0.013 (2)	−0.002 (2)
C30	0.041 (3)	0.026 (3)	0.040 (3)	0.004 (2)	0.020 (3)	−0.004 (2)
C31	0.044 (3)	0.019 (3)	0.044 (4)	0.001 (2)	0.019 (3)	0.002 (2)
C32	0.032 (3)	0.031 (3)	0.033 (3)	−0.006 (2)	0.016 (2)	0.001 (3)
C33	0.017 (2)	0.022 (3)	0.020 (3)	−0.004 (2)	0.003 (2)	−0.001 (2)
C34	0.018 (2)	0.034 (3)	0.017 (3)	−0.005 (2)	−0.001 (2)	−0.001 (2)
C35	0.014 (2)	0.023 (3)	0.020 (3)	0.002 (2)	0.005 (2)	0.005 (2)
C36	0.014 (2)	0.026 (3)	0.024 (3)	0.003 (2)	0.006 (2)	0.001 (2)
C37	0.022 (2)	0.032 (3)	0.023 (3)	0.000 (2)	0.012 (2)	−0.003 (2)
C38	0.016 (2)	0.025 (3)	0.020 (3)	−0.002 (2)	0.000 (2)	−0.003 (2)

Geometric parameters (Å, º) top

O1—C2	1.223 (5)	C13—H13	0.9500
O2—C4	1.373 (5)	C14—C15	1.492 (6)
O2—C6	1.385 (4)	C15—C16	1.453 (6)
O3—C8	1.230 (5)	C16—C17	1.420 (6)
O4—C15	1.252 (5)	C17—C18	1.396 (5)
O5—C17	1.354 (5)	C18—C19	1.375 (5)
O5—H5	0.84 (1)	C18—H18	0.9500
O6—C21	1.231 (5)	C20—C21	1.501 (6)
O7—C25	1.385 (5)	C20—H20A	0.9800
O7—C23	1.395 (5)	C20—H20B	0.9800
O8—C27	1.224 (5)	C20—H20C	0.9800
O9—C34	1.248 (5)	C21—C22	1.464 (6)
O10—C36	1.352 (5)	C22—C23	1.375 (6)
O10—H10	0.84 (1)	C22—C38	1.456 (5)
C1—C2	1.502 (5)	C23—C24	1.461 (5)
C1—H1A	0.9800	C24—H24A	0.9800
C1—H1B	0.9800	C24—H24B	0.9800
C1—H1C	0.9800	C24—H24C	0.9800
C2—C3	1.469 (6)	C25—C26	1.368 (5)
C3—C4	1.361 (5)	C25—C38	1.410 (5)
C3—C19	1.453 (5)	C26—C35	1.424 (5)
C4—C5	1.493 (5)	C26—C27	1.496 (5)
C5—H5A	0.9800	C27—C28	1.488 (6)
C5—H5B	0.9800	C28—C29	1.385 (5)
C5—H5C	0.9800	C28—C33	1.403 (5)
C6—C7	1.374 (5)	C29—C30	1.388 (6)
C6—C19	1.407 (5)	C29—H29	0.9500
C7—C16	1.413 (5)	C30—C31	1.403 (6)
C7—C8	1.479 (6)	C30—H30	0.9500
C8—C9	1.487 (6)	C31—C32	1.383 (6)
C9—C10	1.390 (6)	C31—H31	0.9500
C9—C14	1.393 (5)	C32—C33	1.375 (6)
C10—C11	1.386 (6)	C32—H32	0.9500
C10—H10A	0.9500	C33—C34	1.490 (5)
C11—C12	1.397 (6)	C34—C35	1.447 (6)
C11—H11	0.9500	C35—C36	1.420 (5)
C12—C13	1.383 (6)	C36—C37	1.401 (6)
C12—H12	0.9500	C37—C38	1.380 (5)
C13—C14	1.407 (5)	C37—H37	0.9500

C4—O2—C6	106.6 (3)	C18—C19—C3	134.6 (4)
C17—O5—H5	104 (3)	C6—C19—C3	105.9 (4)
C25—O7—C23	106.9 (3)	C21—C20—H20A	109.5
C36—O10—H10	104 (4)	C21—C20—H20B	109.5
C2—C1—H1A	109.5	H20A—C20—H20B	109.5
C2—C1—H1B	109.5	C21—C20—H20C	109.5
H1A—C1—H1B	109.5	H20A—C20—H20C	109.5
C2—C1—H1C	109.5	H20B—C20—H20C	109.5
H1A—C1—H1C	109.5	O6—C21—C22	118.3 (4)
H1B—C1—H1C	109.5	O6—C21—C20	121.1 (4)
O1—C2—C3	119.6 (4)	C22—C21—C20	120.6 (4)
O1—C2—C1	121.0 (4)	C23—C22—C38	106.7 (4)
C3—C2—C1	119.4 (4)	C23—C22—C21	128.6 (4)
C4—C3—C19	105.8 (4)	C38—C22—C21	124.6 (4)
C4—C3—C2	130.3 (4)	C22—C23—O7	110.7 (4)
C19—C3—C2	123.9 (4)	C22—C23—C24	135.9 (4)
C3—C4—O2	112.2 (4)	O7—C23—C24	113.4 (4)
C3—C4—C5	136.2 (4)	C23—C24—H24A	109.5
O2—C4—C5	111.6 (4)	C23—C24—H24B	109.5
C4—C5—H5A	109.5	H24A—C24—H24B	109.5
C4—C5—H5B	109.5	C23—C24—H24C	109.5
H5A—C5—H5B	109.5	H24A—C24—H24C	109.5
C4—C5—H5C	109.5	H24B—C24—H24C	109.5
H5A—C5—H5C	109.5	C26—C25—O7	126.3 (4)
H5B—C5—H5C	109.5	C26—C25—C38	123.7 (4)
C7—C6—O2	126.4 (4)	O7—C25—C38	110.0 (4)
C7—C6—C19	124.1 (4)	C25—C26—C35	117.0 (4)
O2—C6—C19	109.4 (4)	C25—C26—C27	121.9 (4)
C6—C7—C16	116.5 (4)	C35—C26—C27	121.2 (4)
C6—C7—C8	122.5 (4)	O8—C27—C28	121.4 (4)
C16—C7—C8	121.1 (4)	O8—C27—C26	121.3 (4)
O3—C8—C7	121.5 (4)	C28—C27—C26	117.3 (4)
O3—C8—C9	120.7 (4)	C29—C28—C33	119.9 (4)
C7—C8—C9	117.8 (4)	C29—C28—C27	119.3 (4)
C10—C9—C14	119.9 (4)	C33—C28—C27	120.8 (4)
C10—C9—C8	119.6 (4)	C28—C29—C30	119.8 (4)
C14—C9—C8	120.5 (4)	C28—C29—H29	120.1
C11—C10—C9	120.5 (4)	C30—C29—H29	120.1
C11—C10—H10A	119.8	C29—C30—C31	120.0 (4)
C9—C10—H10A	119.8	C29—C30—H30	120.0
C10—C11—C12	119.8 (4)	C31—C30—H30	120.0
C10—C11—H11	120.1	C32—C31—C30	120.0 (4)
C12—C11—H11	120.1	C32—C31—H31	120.0
C13—C12—C11	120.3 (4)	C30—C31—H31	120.0
C13—C12—H12	119.9	C33—C32—C31	120.1 (4)
C11—C12—H12	119.9	C33—C32—H32	120.0
C12—C13—C14	119.8 (4)	C31—C32—H32	120.0
C12—C13—H13	120.1	C32—C33—C28	120.3 (4)
C14—C13—H13	120.1	C32—C33—C34	118.9 (4)
C9—C14—C13	119.7 (4)	C28—C33—C34	120.8 (4)
C9—C14—C15	120.6 (4)	O9—C34—C35	121.3 (4)
C13—C14—C15	119.7 (4)	O9—C34—C33	119.4 (4)
O4—C15—C16	121.6 (4)	C35—C34—C33	119.3 (4)
O4—C15—C14	119.3 (4)	C26—C35—C36	119.6 (4)
C16—C15—C14	119.0 (4)	C26—C35—C34	120.3 (4)
C7—C16—C17	119.9 (4)	C36—C35—C34	120.0 (4)
C7—C16—C15	120.1 (4)	O10—C36—C37	116.9 (4)
C17—C16—C15	120.0 (4)	O10—C36—C35	121.5 (4)
O5—C17—C18	115.6 (4)	C37—C36—C35	121.6 (4)
O5—C17—C16	122.8 (4)	C38—C37—C36	118.2 (4)
C18—C17—C16	121.6 (4)	C38—C37—H37	120.9
C19—C18—C17	118.5 (4)	C36—C37—H37	120.9
C19—C18—H18	120.8	C37—C38—C25	119.9 (4)
C17—C18—H18	120.8	C37—C38—C22	134.4 (4)
C18—C19—C6	119.5 (4)	C25—C38—C22	105.7 (3)

O1—C2—C3—C4	173.4 (4)	O6—C21—C22—C23	−176.5 (4)
C1—C2—C3—C4	−8.3 (7)	C20—C21—C22—C23	2.5 (7)
O1—C2—C3—C19	−4.8 (6)	O6—C21—C22—C38	0.8 (7)
C1—C2—C3—C19	173.4 (4)	C20—C21—C22—C38	179.8 (4)
C19—C3—C4—O2	−1.9 (5)	C38—C22—C23—O7	−1.3 (5)
C2—C3—C4—O2	179.6 (4)	C21—C22—C23—O7	176.4 (4)
C19—C3—C4—C5	177.4 (5)	C38—C22—C23—C24	178.7 (5)
C2—C3—C4—C5	−1.1 (8)	C21—C22—C23—C24	−3.6 (9)
C6—O2—C4—C3	1.0 (4)	C25—O7—C23—C22	0.5 (5)
C6—O2—C4—C5	−178.5 (3)	C25—O7—C23—C24	−179.5 (3)
C4—O2—C6—C7	179.6 (4)	C23—O7—C25—C26	178.8 (4)
C4—O2—C6—C19	0.4 (4)	C23—O7—C25—C38	0.6 (4)
O2—C6—C7—C16	−178.5 (4)	O7—C25—C26—C35	−176.4 (4)
C19—C6—C7—C16	0.5 (6)	C38—C25—C26—C35	1.7 (6)
O2—C6—C7—C8	1.4 (7)	O7—C25—C26—C27	2.4 (6)
C19—C6—C7—C8	−179.6 (4)	C38—C25—C26—C27	−179.5 (4)
C6—C7—C8—O3	8.5 (6)	C25—C26—C27—O8	4.7 (6)
C16—C7—C8—O3	−171.5 (4)	C35—C26—C27—O8	−176.5 (4)
C6—C7—C8—C9	−171.4 (4)	C25—C26—C27—C28	−175.1 (4)
C16—C7—C8—C9	8.5 (6)	C35—C26—C27—C28	3.7 (6)
O3—C8—C9—C10	−8.8 (6)	O8—C27—C28—C29	−3.1 (6)
C7—C8—C9—C10	171.2 (4)	C26—C27—C28—C29	176.7 (4)
O3—C8—C9—C14	173.8 (4)	O8—C27—C28—C33	176.1 (4)
C7—C8—C9—C14	−6.3 (6)	C26—C27—C28—C33	−4.1 (6)
C14—C9—C10—C11	0.9 (6)	C33—C28—C29—C30	1.7 (6)
C8—C9—C10—C11	−176.5 (4)	C27—C28—C29—C30	−179.1 (4)
C9—C10—C11—C12	−0.5 (7)	C28—C29—C30—C31	−2.0 (7)
C10—C11—C12—C13	−1.0 (7)	C29—C30—C31—C32	1.6 (7)
C11—C12—C13—C14	2.1 (7)	C30—C31—C32—C33	−0.9 (7)
C10—C9—C14—C13	0.2 (6)	C31—C32—C33—C28	0.6 (7)
C8—C9—C14—C13	177.6 (4)	C31—C32—C33—C34	179.7 (4)
C10—C9—C14—C15	−179.3 (4)	C29—C28—C33—C32	−1.0 (6)
C8—C9—C14—C15	−1.8 (6)	C27—C28—C33—C32	179.8 (4)
C12—C13—C14—C9	−1.7 (6)	C29—C28—C33—C34	179.9 (4)
C12—C13—C14—C15	177.7 (4)	C27—C28—C33—C34	0.7 (6)
C9—C14—C15—O4	−173.1 (4)	C32—C33—C34—O9	2.9 (6)
C13—C14—C15—O4	7.5 (6)	C28—C33—C34—O9	−178.1 (4)
C9—C14—C15—C16	8.0 (6)	C32—C33—C34—C35	−175.8 (4)
C13—C14—C15—C16	−171.4 (4)	C28—C33—C34—C35	3.3 (6)
C6—C7—C16—C17	−1.8 (6)	C25—C26—C35—C36	−1.0 (6)
C8—C7—C16—C17	178.3 (4)	C27—C26—C35—C36	−179.8 (4)
C6—C7—C16—C15	177.5 (4)	C25—C26—C35—C34	179.0 (4)
C8—C7—C16—C15	−2.4 (6)	C27—C26—C35—C34	0.2 (6)
O4—C15—C16—C7	175.3 (4)	O9—C34—C35—C26	177.7 (4)
C14—C15—C16—C7	−5.8 (6)	C33—C34—C35—C26	−3.7 (6)
O4—C15—C16—C17	−5.4 (7)	O9—C34—C35—C36	−2.3 (6)
C14—C15—C16—C17	173.5 (4)	C33—C34—C35—C36	176.3 (4)
C7—C16—C17—O5	−178.6 (4)	C26—C35—C36—O10	178.0 (4)
C15—C16—C17—O5	2.1 (6)	C34—C35—C36—O10	−2.0 (6)
C7—C16—C17—C18	1.9 (6)	C26—C35—C36—C37	0.0 (6)
C15—C16—C17—C18	−177.5 (4)	C34—C35—C36—C37	180.0 (4)
O5—C17—C18—C19	180.0 (3)	O10—C36—C37—C38	−177.7 (4)
C16—C17—C18—C19	−0.5 (6)	C35—C36—C37—C38	0.3 (6)
C17—C18—C19—C6	−0.9 (6)	C36—C37—C38—C25	0.3 (6)
C17—C18—C19—C3	−178.7 (4)	C36—C37—C38—C22	177.9 (4)
C7—C6—C19—C18	0.9 (6)	C26—C25—C38—C37	−1.3 (6)
O2—C6—C19—C18	−179.9 (3)	O7—C25—C38—C37	177.0 (4)
C7—C6—C19—C3	179.3 (4)	C26—C25—C38—C22	−179.6 (4)
O2—C6—C19—C3	−1.5 (5)	O7—C25—C38—C22	−1.3 (4)
C4—C3—C19—C18	−179.9 (4)	C23—C22—C38—C37	−176.4 (5)
C2—C3—C19—C18	−1.3 (7)	C21—C22—C38—C37	5.9 (7)
C4—C3—C19—C6	2.1 (5)	C23—C22—C38—C25	1.5 (4)
C2—C3—C19—C6	−179.3 (4)	C21—C22—C38—C25	−176.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.84 (1)	1.82 (2)	2.596 (4)	153 (4)
O10—H10···O9	0.84 (1)	1.77 (3)	2.552 (4)	153 (6)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂O₅
M_r	320.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.5739 (9), 22.0375 (12), 10.7453 (8)
β (°)	110.342 (8)
V (Å³)	2791.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.05 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.962, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	12061, 4905, 2305
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.149, 0.95
No. of reflections	4905
No. of parameters	445
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.84 (1)	1.82 (2)	2.596 (4)	153 (4)
O10—H10···O9	0.84 (1)	1.77 (3)	2.552 (4)	153 (6)

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Boddy, I. K., Cambie, R. C., Rutledge, P. S. & Woodgate, P. D. (1986). Aust. J. Chem. 39, 2075–2088. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar