9-(4-Hy­droxy-3-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6-tetra­hydro-9H-xanthene-1,8(2H,7H)-dione

Hasanudin, N.; Abdul Rahim, A.S.; Mohamed, N.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810020258

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1538-o1539

doi:10.1107/S1600536810020258

Open

access

9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6-tetrahydro-9H-xanthene-1,8(2H,7H)-dione

Noorhafizah Hasanudin,^a Aisyah Saad Abdul Rahim,^a ‡ Nornisah Mohamed,^a Ching Kheng Quah ^b § and Hoong-Kun Fun ^b ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 17 May 2010; accepted 28 May 2010; online 5 June 2010)

In the title compound, C₂₄H₂₈O₅, the two cyclohexene rings adopt envelope conformations, and the planes through the coplanar atoms makes dihedral angles of 82.86 (6) and 77.90 (6)° with the benzene ring. The two cyclohexene rings make a dihedral angle of 5.33 (6)° between their least-squares planes. The pyran ring adopts a flattened boat conformation. In the crystal packing, molecules are linked into two-dimensional networks parallel to the ab plane via O—H⋯O and C—H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Venkatesan et al. (2008 ). For general background to and the biological activity of xanthene derivatives, see: Hafez et al. (2008 ); Ashry et al. (2006 ); Sill & Sweet (1977 ); Ion (1997 ); Chibale et al. (2003 ). For reference bond lengths, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₈O₅
M_r = 396.46
Orthorhombic, P b c a
a = 11.4861 (10) Å
b = 11.8659 (11) Å
c = 30.087 (3) Å
V = 4100.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.24 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.979
26584 measured reflections
5972 independent reflections
4634 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.136
S = 1.06
5972 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H14O⋯O3ⁱ	0.86 (2)	1.95 (2)	2.7319 (13)	151 (2)
C2—H2A⋯O2ⁱⁱ	0.97	2.55	3.5003 (16)	165
C20—H20C⋯O2ⁱⁱⁱ	0.96	2.58	3.4646 (17)	154
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020258/rz2454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020258/rz2454Isup2.hkl

checkCIF report

Comment top

Xanthene derivatives especially benzoxanthenes are well-known in organic synthesis due to their biologically active properties such as anti-inflammatory (Hafez et al., 2008), antimicrobial (Ashry et al., 2006), antiviral (Sill & Sweet, 1977) activities and as well as being used in photodynamic therapy (Ion, 1997). Molecules based on the 9,9-dimethylxanthene moiety have inhibitory activity towards trypanothione reductase (TryR) (Chibale et al., 2003). In view of its importance in this field, the crystal structure of the title compound was determined and the results are presented here.

The bond lengths (Allen et al., 1987) and angles in the title compound (Fig. 1) are within normal ranges. The two cyclohexene rings, C1—C6 and C8—C13, adopt an envelope conformation, and the plane through the coplanar atoms makes dihedral angles of 82.86 (6)° and 77.90 (6)°, respectively, with the benzene ring (C14—C19). The puckering parameters (Cremer & Pople, 1975) are Q = 0.4872 (14) Å, Θ = 125.01 (16)° and ϕ = 307.7 (2)° for the C1—C6 ring, Q = 0.4698 (14) Å, Θ = 56.48 (17)° and ϕ = 172.6 (2) ° for the C8—C13 ring. The two cyclohexene rings make a dihedral angle of 5.33 (6)° between their least-squares planes. The pyran ring (O1/C1/C6—C8/C13) adopts a flattened boat conformation with atoms C7 and O1 deviating by 0.150 (1) and 0.111 (1) Å, respectively, from the base of the boat.

In the crystal packing (Fig. 2), the molecules are linked into two-dimensional networks parallel to the ab plane via O5–H14O···O3, C2–H2A···O2 and C20–H20C···O2 interactions (Table 1).

Related literature top

For the synthesis of the title compound, see: Venkatesan et al. (2008). For general background to and the biological activity of xanthene derivatives, see: Hafez et al. (2008); Ashry et al. (2006); Sill & Sweet (1977); Ion (1997); Chibale et al. (2003). For reference bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The synthesis of the title compound was performed according to the procedure described in the literature (Venkatesan et al., 2008). A mixture of vanilin (90 mg, 0.59 mmol), dimedone (160 mg, 1.14 mmol), p-toluenesulfonic acid (2 mg) in MeOH (4 ml) and water (2 ml) was heated to 50 °C in N₂ atmosphere for about 20 min. Good quality crystals suitable for characterisation by X-ray crystallography were obtained by recrystallisation from hot methanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. The crystal structure of the title compound viewed along the c axis. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6-tetrahydro- 9H-xanthene-1,8(2H,7H)-dione top

Crystal data top

C₂₄H₂₈O₅	F(000) = 1696
M_r = 396.46	D_x = 1.284 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5544 reflections
a = 11.4861 (10) Å	θ = 2.2–31.4°
b = 11.8659 (11) Å	µ = 0.09 mm⁻¹
c = 30.087 (3) Å	T = 100 K
V = 4100.6 (6) Å³	Block, colourless
Z = 8	0.35 × 0.30 × 0.24 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5972 independent reflections
Radiation source: fine-focus sealed tube	4634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→12
T_min = 0.970, T_max = 0.979	k = −16→16
26584 measured reflections	l = −20→42

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0729P)² + 0.8139P] where P = (F_o² + 2F_c²)/3
5972 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₄H₂₈O₅	V = 4100.6 (6) Å³
M_r = 396.46	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.4861 (10) Å	µ = 0.09 mm⁻¹
b = 11.8659 (11) Å	T = 100 K
c = 30.087 (3) Å	0.35 × 0.30 × 0.24 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5972 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4634 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.979	R_int = 0.046
26584 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.57 e Å⁻³
5972 reflections	Δρ_min = −0.38 e Å⁻³
271 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.28861 (7)	0.40281 (8)	0.37337 (3)	0.01617 (19)
O2	0.01386 (8)	0.44676 (8)	0.26832 (3)	0.0228 (2)
O3	−0.01627 (8)	0.68315 (9)	0.41472 (4)	0.0257 (2)
O4	0.35090 (8)	0.35573 (8)	0.36534 (3)	0.0207 (2)
O5	0.27890 (8)	0.17322 (8)	0.41056 (4)	0.0225 (2)
C1	−0.23302 (10)	0.38185 (10)	0.33355 (4)	0.0146 (2)
C2	−0.30172 (10)	0.30335 (11)	0.30502 (4)	0.0170 (2)
H2A	−0.3616	0.3454	0.2895	0.020*
H2B	−0.3398	0.2477	0.3236	0.020*
C3	−0.22358 (11)	0.24318 (11)	0.27099 (4)	0.0190 (3)
C4	−0.15068 (12)	0.33410 (12)	0.24770 (5)	0.0215 (3)
H4A	−0.0983	0.2979	0.2268	0.026*
H4B	−0.2023	0.3826	0.2308	0.026*
C5	−0.08000 (11)	0.40592 (10)	0.27917 (4)	0.0171 (2)
C6	−0.12984 (10)	0.42841 (10)	0.32340 (4)	0.0142 (2)
C7	−0.05937 (10)	0.49443 (10)	0.35702 (4)	0.0142 (2)
H7A	−0.0228	0.5590	0.3423	0.017*
C8	−0.14118 (10)	0.53630 (10)	0.39271 (4)	0.0143 (2)
C9	−0.10776 (11)	0.63245 (11)	0.42079 (4)	0.0172 (2)
C10	−0.19236 (11)	0.67093 (11)	0.45628 (5)	0.0195 (3)
H10A	−0.2428	0.7283	0.4438	0.023*
H10B	−0.1487	0.7054	0.4803	0.023*
C11	−0.26798 (11)	0.57635 (11)	0.47544 (4)	0.0185 (3)
C12	−0.32808 (11)	0.51647 (11)	0.43638 (4)	0.0182 (3)
H12A	−0.3646	0.4479	0.4471	0.022*
H12B	−0.3888	0.5649	0.4247	0.022*
C13	−0.24524 (10)	0.48756 (10)	0.39991 (4)	0.0145 (2)
C14	0.03504 (10)	0.41644 (10)	0.37528 (4)	0.0144 (2)
C15	0.15186 (10)	0.43068 (10)	0.36324 (4)	0.0150 (2)
H15A	0.1742	0.4937	0.3470	0.018*
C16	0.23459 (10)	0.35118 (11)	0.37548 (4)	0.0154 (2)
C17	0.20159 (11)	0.25532 (10)	0.39955 (4)	0.0163 (2)
C18	0.08671 (11)	0.24362 (11)	0.41294 (5)	0.0192 (3)
H18A	0.0648	0.1820	0.4301	0.023*
C19	0.00419 (11)	0.32338 (11)	0.40088 (5)	0.0186 (3)
H19A	−0.0726	0.3146	0.4100	0.022*
C20	−0.14395 (12)	0.15751 (11)	0.29401 (5)	0.0253 (3)
H20A	−0.1906	0.1025	0.3092	0.038*
H20B	−0.0951	0.1957	0.3151	0.038*
H20C	−0.0963	0.1207	0.2722	0.038*
C21	−0.29993 (13)	0.18345 (13)	0.23661 (5)	0.0291 (3)
H21A	−0.3498	0.1304	0.2514	0.044*
H21B	−0.2513	0.1444	0.2157	0.044*
H21C	−0.3465	0.2381	0.2212	0.044*
C22	−0.36133 (12)	0.62585 (14)	0.50611 (5)	0.0282 (3)
H22A	−0.3246	0.6625	0.5308	0.042*
H22B	−0.4107	0.5664	0.5168	0.042*
H22C	−0.4072	0.6796	0.4899	0.042*
C23	−0.19191 (13)	0.49357 (13)	0.50166 (5)	0.0280 (3)
H23A	−0.1551	0.5324	0.5259	0.042*
H23B	−0.1334	0.4626	0.4824	0.042*
H23C	−0.2396	0.4338	0.5131	0.042*
C24	0.39966 (11)	0.46439 (12)	0.35714 (5)	0.0238 (3)
H24A	0.4831	0.4594	0.3577	0.036*
H24B	0.3739	0.5160	0.3797	0.036*
H24C	0.3748	0.4908	0.3285	0.036*
H14O	0.3488 (19)	0.1956 (19)	0.4055 (8)	0.047 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0129 (4)	0.0191 (4)	0.0165 (4)	−0.0030 (3)	0.0024 (3)	−0.0032 (3)
O2	0.0224 (5)	0.0237 (5)	0.0223 (5)	−0.0030 (4)	0.0075 (4)	0.0022 (4)
O3	0.0185 (5)	0.0247 (5)	0.0339 (6)	−0.0067 (4)	0.0031 (4)	−0.0047 (4)
O4	0.0105 (4)	0.0246 (5)	0.0272 (5)	0.0030 (3)	0.0023 (3)	0.0053 (4)
O5	0.0165 (5)	0.0195 (5)	0.0315 (5)	0.0044 (4)	−0.0038 (4)	0.0044 (4)
C1	0.0140 (5)	0.0146 (5)	0.0152 (5)	0.0022 (4)	0.0005 (4)	0.0006 (4)
C2	0.0153 (5)	0.0179 (5)	0.0179 (6)	−0.0010 (4)	−0.0009 (4)	−0.0017 (5)
C3	0.0214 (6)	0.0169 (6)	0.0187 (6)	−0.0027 (5)	0.0022 (5)	−0.0026 (5)
C4	0.0263 (7)	0.0216 (6)	0.0166 (6)	−0.0029 (5)	0.0036 (5)	−0.0008 (5)
C5	0.0205 (6)	0.0143 (5)	0.0166 (6)	0.0021 (4)	0.0024 (5)	0.0028 (5)
C6	0.0132 (5)	0.0135 (5)	0.0159 (5)	0.0021 (4)	0.0003 (4)	0.0024 (4)
C7	0.0106 (5)	0.0146 (5)	0.0173 (6)	0.0004 (4)	0.0012 (4)	0.0017 (4)
C8	0.0114 (5)	0.0148 (5)	0.0166 (5)	0.0015 (4)	−0.0001 (4)	0.0015 (4)
C9	0.0144 (5)	0.0166 (5)	0.0206 (6)	0.0004 (4)	−0.0021 (5)	0.0007 (5)
C10	0.0165 (6)	0.0202 (6)	0.0219 (6)	−0.0002 (5)	−0.0008 (5)	−0.0049 (5)
C11	0.0155 (5)	0.0237 (6)	0.0163 (6)	−0.0008 (5)	0.0010 (5)	−0.0023 (5)
C12	0.0127 (5)	0.0229 (6)	0.0191 (6)	−0.0005 (4)	0.0017 (4)	−0.0036 (5)
C13	0.0119 (5)	0.0161 (5)	0.0156 (5)	0.0006 (4)	−0.0011 (4)	−0.0001 (5)
C14	0.0116 (5)	0.0152 (5)	0.0164 (5)	0.0014 (4)	−0.0005 (4)	−0.0004 (4)
C15	0.0129 (5)	0.0156 (5)	0.0164 (5)	−0.0004 (4)	0.0002 (4)	0.0008 (4)
C16	0.0112 (5)	0.0199 (6)	0.0151 (5)	0.0013 (4)	−0.0007 (4)	−0.0016 (5)
C17	0.0141 (5)	0.0177 (6)	0.0171 (6)	0.0026 (4)	−0.0031 (4)	−0.0001 (5)
C18	0.0169 (6)	0.0173 (6)	0.0235 (6)	−0.0005 (4)	−0.0003 (5)	0.0043 (5)
C19	0.0130 (5)	0.0193 (6)	0.0235 (6)	−0.0002 (4)	0.0016 (5)	0.0028 (5)
C20	0.0260 (7)	0.0145 (6)	0.0354 (8)	0.0013 (5)	0.0065 (6)	0.0001 (6)
C21	0.0334 (8)	0.0288 (7)	0.0252 (7)	−0.0090 (6)	0.0034 (6)	−0.0102 (6)
C22	0.0221 (7)	0.0409 (8)	0.0216 (7)	−0.0028 (6)	0.0033 (5)	−0.0115 (6)
C23	0.0301 (7)	0.0339 (8)	0.0200 (7)	0.0016 (6)	−0.0021 (6)	0.0045 (6)
C24	0.0143 (6)	0.0272 (7)	0.0298 (7)	−0.0045 (5)	0.0002 (5)	−0.0047 (6)

Geometric parameters (Å, º) top

O1—C13	1.3772 (15)	C11—C22	1.5317 (18)
O1—C1	1.3802 (14)	C11—C23	1.5333 (19)
O2—C5	1.2263 (15)	C11—C12	1.5370 (18)
O3—C9	1.2246 (15)	C12—C13	1.4922 (17)
O4—C16	1.3714 (15)	C12—H12A	0.9700
O4—C24	1.4272 (17)	C12—H12B	0.9700
O5—C17	1.3591 (15)	C14—C19	1.3922 (18)
O5—H14O	0.86 (2)	C14—C15	1.4001 (16)
C1—C6	1.3427 (17)	C15—C16	1.3886 (17)
C1—C2	1.4924 (17)	C15—H15A	0.9300
C2—C3	1.5372 (18)	C16—C17	1.4007 (18)
C2—H2A	0.9700	C17—C18	1.3867 (18)
C2—H2B	0.9700	C18—C19	1.3877 (18)
C3—C21	1.5301 (19)	C18—H18A	0.9300
C3—C20	1.5329 (19)	C19—H19A	0.9300
C3—C4	1.5350 (18)	C20—H20A	0.9600
C4—C5	1.5106 (19)	C20—H20B	0.9600
C4—H4A	0.9700	C20—H20C	0.9600
C4—H4B	0.9700	C21—H21A	0.9600
C5—C6	1.4730 (17)	C21—H21B	0.9600
C6—C7	1.5140 (17)	C21—H21C	0.9600
C7—C8	1.5108 (17)	C22—H22A	0.9600
C7—C14	1.5278 (16)	C22—H22B	0.9600
C7—H7A	0.9800	C22—H22C	0.9600
C8—C13	1.3454 (16)	C23—H23A	0.9600
C8—C9	1.4706 (17)	C23—H23B	0.9600
C9—C10	1.5143 (18)	C23—H23C	0.9600
C10—C11	1.5317 (18)	C24—H24A	0.9600
C10—H10A	0.9700	C24—H24B	0.9600
C10—H10B	0.9700	C24—H24C	0.9600

C13—O1—C1	117.88 (9)	C11—C12—H12A	109.1
C16—O4—C24	117.15 (10)	C13—C12—H12B	109.1
C17—O5—H14O	110.3 (15)	C11—C12—H12B	109.1
C6—C1—O1	122.11 (11)	H12A—C12—H12B	107.8
C6—C1—C2	126.34 (11)	C8—C13—O1	122.80 (11)
O1—C1—C2	111.55 (10)	C8—C13—C12	125.88 (11)
C1—C2—C3	111.36 (10)	O1—C13—C12	111.32 (10)
C1—C2—H2A	109.4	C19—C14—C15	118.86 (11)
C3—C2—H2A	109.4	C19—C14—C7	119.92 (10)
C1—C2—H2B	109.4	C15—C14—C7	120.94 (11)
C3—C2—H2B	109.4	C16—C15—C14	120.35 (12)
H2A—C2—H2B	108.0	C16—C15—H15A	119.8
C21—C3—C20	109.88 (12)	C14—C15—H15A	119.8
C21—C3—C4	109.24 (11)	O4—C16—C15	125.52 (12)
C20—C3—C4	110.30 (11)	O4—C16—C17	114.24 (11)
C21—C3—C2	109.31 (11)	C15—C16—C17	120.23 (11)
C20—C3—C2	110.83 (11)	O5—C17—C18	118.62 (12)
C4—C3—C2	107.22 (10)	O5—C17—C16	122.09 (11)
C5—C4—C3	113.79 (11)	C18—C17—C16	119.28 (11)
C5—C4—H4A	108.8	C17—C18—C19	120.37 (12)
C3—C4—H4A	108.8	C17—C18—H18A	119.8
C5—C4—H4B	108.8	C19—C18—H18A	119.8
C3—C4—H4B	108.8	C18—C19—C14	120.78 (12)
H4A—C4—H4B	107.7	C18—C19—H19A	119.6
O2—C5—C6	120.71 (12)	C14—C19—H19A	119.6
O2—C5—C4	121.91 (12)	C3—C20—H20A	109.5
C6—C5—C4	117.36 (11)	C3—C20—H20B	109.5
C1—C6—C5	118.29 (11)	H20A—C20—H20B	109.5
C1—C6—C7	122.20 (11)	C3—C20—H20C	109.5
C5—C6—C7	119.31 (10)	H20A—C20—H20C	109.5
C8—C7—C6	108.21 (10)	H20B—C20—H20C	109.5
C8—C7—C14	112.65 (10)	C3—C21—H21A	109.5
C6—C7—C14	107.84 (10)	C3—C21—H21B	109.5
C8—C7—H7A	109.4	H21A—C21—H21B	109.5
C6—C7—H7A	109.4	C3—C21—H21C	109.5
C14—C7—H7A	109.4	H21A—C21—H21C	109.5
C13—C8—C9	118.22 (11)	H21B—C21—H21C	109.5
C13—C8—C7	121.72 (11)	C11—C22—H22A	109.5
C9—C8—C7	120.07 (10)	C11—C22—H22B	109.5
O3—C9—C8	121.30 (12)	H22A—C22—H22B	109.5
O3—C9—C10	120.51 (12)	C11—C22—H22C	109.5
C8—C9—C10	118.14 (11)	H22A—C22—H22C	109.5
C9—C10—C11	114.09 (11)	H22B—C22—H22C	109.5
C9—C10—H10A	108.7	C11—C23—H23A	109.5
C11—C10—H10A	108.7	C11—C23—H23B	109.5
C9—C10—H10B	108.7	H23A—C23—H23B	109.5
C11—C10—H10B	108.7	C11—C23—H23C	109.5
H10A—C10—H10B	107.6	H23A—C23—H23C	109.5
C22—C11—C10	110.04 (11)	H23B—C23—H23C	109.5
C22—C11—C23	109.54 (12)	O4—C24—H24A	109.5
C10—C11—C23	109.87 (11)	O4—C24—H24B	109.5
C22—C11—C12	108.88 (10)	H24A—C24—H24B	109.5
C10—C11—C12	107.80 (11)	O4—C24—H24C	109.5
C23—C11—C12	110.68 (11)	H24A—C24—H24C	109.5
C13—C12—C11	112.46 (10)	H24B—C24—H24C	109.5
C13—C12—H12A	109.1

C13—O1—C1—C6	10.47 (17)	C9—C10—C11—C22	−172.25 (11)
C13—O1—C1—C2	−169.61 (10)	C9—C10—C11—C23	67.06 (14)
C6—C1—C2—C3	22.80 (18)	C9—C10—C11—C12	−53.64 (14)
O1—C1—C2—C3	−157.11 (10)	C22—C11—C12—C13	167.54 (12)
C1—C2—C3—C21	−168.27 (11)	C10—C11—C12—C13	48.19 (14)
C1—C2—C3—C20	70.47 (13)	C23—C11—C12—C13	−71.99 (14)
C1—C2—C3—C4	−49.96 (14)	C9—C8—C13—O1	174.91 (11)
C21—C3—C4—C5	174.64 (12)	C7—C8—C13—O1	−5.31 (18)
C20—C3—C4—C5	−64.49 (15)	C9—C8—C13—C12	−4.82 (19)
C2—C3—C4—C5	56.29 (14)	C7—C8—C13—C12	174.95 (12)
C3—C4—C5—O2	148.98 (12)	C1—O1—C13—C8	−12.05 (17)
C3—C4—C5—C6	−32.87 (16)	C1—O1—C13—C12	167.72 (10)
O1—C1—C6—C5	−176.84 (10)	C11—C12—C13—C8	−21.12 (18)
C2—C1—C6—C5	3.25 (18)	C11—C12—C13—O1	159.11 (10)
O1—C1—C6—C7	8.37 (18)	C8—C7—C14—C19	52.88 (15)
C2—C1—C6—C7	−171.54 (11)	C6—C7—C14—C19	−66.46 (15)
O2—C5—C6—C1	179.82 (11)	C8—C7—C14—C15	−133.24 (12)
C4—C5—C6—C1	1.65 (17)	C6—C7—C14—C15	107.43 (13)
O2—C5—C6—C7	−5.23 (17)	C19—C14—C15—C16	2.08 (19)
C4—C5—C6—C7	176.59 (11)	C7—C14—C15—C16	−171.87 (11)
C1—C6—C7—C8	−22.67 (15)	C24—O4—C16—C15	25.08 (18)
C5—C6—C7—C8	162.59 (10)	C24—O4—C16—C17	−156.10 (12)
C1—C6—C7—C14	99.45 (13)	C14—C15—C16—O4	179.50 (12)
C5—C6—C7—C14	−75.29 (13)	C14—C15—C16—C17	0.74 (19)
C6—C7—C8—C13	21.08 (15)	O4—C16—C17—O5	−1.71 (18)
C14—C7—C8—C13	−98.04 (13)	C15—C16—C17—O5	177.18 (12)
C6—C7—C8—C9	−159.15 (11)	O4—C16—C17—C18	177.85 (12)
C14—C7—C8—C9	81.73 (14)	C15—C16—C17—C18	−3.26 (19)
C13—C8—C9—O3	−177.09 (12)	O5—C17—C18—C19	−177.48 (12)
C7—C8—C9—O3	3.13 (18)	C16—C17—C18—C19	3.0 (2)
C13—C8—C9—C10	0.12 (17)	C17—C18—C19—C14	−0.1 (2)
C7—C8—C9—C10	−179.65 (11)	C15—C14—C19—C18	−2.4 (2)
O3—C9—C10—C11	−152.16 (12)	C7—C14—C19—C18	171.61 (12)
C8—C9—C10—C11	30.60 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H14O···O3ⁱ	0.86 (2)	1.95 (2)	2.7319 (13)	151 (2)
C2—H2A···O2ⁱⁱ	0.97	2.55	3.5003 (16)	165
C20—H20C···O2ⁱⁱⁱ	0.96	2.58	3.4646 (17)	154

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈O₅
M_r	396.46
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	11.4861 (10), 11.8659 (11), 30.087 (3)
V (Å³)	4100.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.30 × 0.24

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	26584, 5972, 4634
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.136, 1.06
No. of reflections	5972
No. of parameters	271
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H14O···O3ⁱ	0.86 (2)	1.95 (2)	2.7319 (13)	151 (2)
C2—H2A···O2ⁱⁱ	0.9700	2.5500	3.5003 (16)	165.00
C20—H20C···O2ⁱⁱⁱ	0.9600	2.5800	3.4646 (17)	154.00

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

Footnotes

‡Additional correspondence author, e-mail: aisyah@usm.my.

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NH, ASAR and NM are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the University Research Grant (1001/PFARMASI/815026). HKF and CKQ thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ also thanks USM for the award of USM Fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Ashry, E. S. H. E., Awad, L. F., Ibrahim, E. S. I. & Bdeewy, O. K. (2006). Arkivoc, 2, 178–186. CrossRef Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chibale, K., Visser, M., Schalkwyk, D., Smith, P. J., Saravanamuthu, A. & Fairlamb, A. H. (2003). Tetrahedron, 59, 2289–2296. Web of Science CrossRef CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Hafez, H. N., Hegab, M. I., Ahmed-Farag, I. S. & El-Gazzar, A. B. A. (2008). Bioorg. Med. Chem. Lett. 18, 4538–4543. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ion, R. M. (1997). Prog. Catal. 2, 55–76. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sill, A. D. & Sweet, F. W. (1977). US Patent No. 4008240. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Venkatesan, K., Pujari, S. S., Lahoti, R. J. & Srinivasan, K. V. (2008). Ultrason. Sonochem. 15, 548–553. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.