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

Fun, H.-K.; Loh, W.-S.; Rajesh, K.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S160053681102527X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1876-o1877

doi:10.1107/S160053681102527X

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

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § K. Rajesh,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 23 June 2011; accepted 27 June 2011; online 2 July 2011)

In the title compound, C₂₃H₂₆O₄, the two cyclohexene rings adopt envelope conformations whereas the pyran ring adopts a boat conformation. In the crystal, pairs of intermolecular O—H⋯O hydrogen bonds link the molecules into inversion dimers.

Related literature

For background to xanthene derivatives and their microbial activity, see: Jonathan et al. (1988 ); Hatakeyama et al. (1988 ); Shchekotikhin & Nikolaeva (2006 ); Hilderbrand & Weissleder (2007 ); Pohlers & Scaiano (1997 ); Knight & Stephens (1989 ); Reddy et al. (2010 ); Rathore et al. (2009 ); Rajesh et al. (2010 ); Mookiah et al. (2009 ). For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Odabaşoğlu et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₂₆O₄
M_r = 366.44
Triclinic, $[P \overline 1]$
a = 9.3525 (1) Å
b = 10.2140 (1) Å
c = 11.6913 (1) Å
α = 67.271 (1)°
β = 76.119 (1)°
γ = 69.419 (1)°
V = 957.32 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.43 × 0.37 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.964, T_max = 0.979
31226 measured reflections
8415 independent reflections
7287 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.119
S = 1.05
8415 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O2ⁱ	0.851 (18)	1.910 (17)	2.7423 (9)	165.6 (17)
Symmetry code: (i) -x, -y+2, -z+1.

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/S160053681102527X/is2739sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102527X/is2739Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102527X/is2739Isup3.cml

checkCIF report

Comment top

Xanthenes are known for possessing various biological properties including antibacterial, antiviral and anti-inflammatory activities (Jonathan et al., 1988). In particular, xanthenedione derivatives constitute a structural unit in several natural products (Hatakeyama et al., 1988), and they are valuable synthons because of the inherent reactivity of the inbuilt pyran ring (Shchekotikhin et al., 2006). Xanthene derivatives are also very useful and important organic compounds widely used as dye (Hilderbrand et al., 2007), in laser technologies (Pohlers et al., 1997), and fluorescent materials for visualization of biomolecules (Knight et al., 1989). The structural resemblance of xanthenes to 1,4-dihydropyridines which was our area of interest (Reddy et al., 2010; Rathore et al., 2009; Rajesh et al., 2010; Mookiah et al., 2009), and which can function as calcium channel blockers made us to focus on xanthenes and its synthesis.

In the title compound (Fig. 1), the cyclohexene (C1–C6 & C8–C13) and the pyran (O1/C1/C6–C8/C13) rings are not planar, having puckering amplitudes, Q of 0.4840 (8), 0.4538 (8) and 0.1049 (8) Å, respectively. The cyclohexene rings (C1–C6 & C8–C13) adopt envelope conformations [ϕ = 118.78 (11)° and Θ = 58.70 (9)°; ϕ = 3.56 (12)° and Θ = 120.92 (10)°] whereas the pyran ring adopts a boat conformation [ϕ = 355.6 (5)° and 114.4 (4)°; Cremer & Pople, 1975). Bond lengths and angles are comparable to the related structure (Odabaşoğlu et al., 2008).

In the crystal packing (Fig. 2), intermolecular O4—H1O4···O2 hydrogen bonds (Table 1) link the molecules into dimers.

Related literature top

For background to xanthene derivatives and their microbial activity, see: Jonathan et al. (1988); Hatakeyama et al. (1988); Shchekotikhin et al. (2006); Hilderbrand et al. (2007); Pohlers et al. (1997); Knight & Stephens (1989); Reddy et al. (2010); Rathore et al. (2009); Rajesh et al. (2010); Mookiah et al. (2009). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For a related structure, see: Odabaşoğlu et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of p-hydroxybenzaldehyde (0.5 g, 8 mmol) and 5,5-dimethyl-1,3-cyclohexanedione (1.15 g, 1.6 mmol) were mixed along with 15 ml of ethylene glycol and then heated at 70 °C for about 1.5 h. The progress of the reaction was monitored by TLC. After confirming that the reaction was completed, the reaction mixture was allowed to cool to room temperature and poured it onto water. The solid obtained was filtered, dried and recrystalized from chloroform/methanol (1:1) to yield colourless crystals (m.p. 519–521 K).

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 and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

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

Crystal data top

C₂₃H₂₆O₄	Z = 2
M_r = 366.44	F(000) = 392
Triclinic, P1	D_x = 1.271 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3525 (1) Å	Cell parameters from 9935 reflections
b = 10.2140 (1) Å	θ = 2.3–35.1°
c = 11.6913 (1) Å	µ = 0.09 mm⁻¹
α = 67.271 (1)°	T = 100 K
β = 76.119 (1)°	Block, colourless
γ = 69.419 (1)°	0.43 × 0.37 × 0.25 mm
V = 957.32 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8415 independent reflections
Radiation source: fine-focus sealed tube	7287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 35.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.964, T_max = 0.979	k = −14→16
31226 measured reflections	l = −17→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0652P)² + 0.1943P] where P = (F_o² + 2F_c²)/3
8415 reflections	(Δ/σ)_max = 0.001
252 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₆O₄	γ = 69.419 (1)°
M_r = 366.44	V = 957.32 (2) Å³
Triclinic, P1	Z = 2
a = 9.3525 (1) Å	Mo Kα radiation
b = 10.2140 (1) Å	µ = 0.09 mm⁻¹
c = 11.6913 (1) Å	T = 100 K
α = 67.271 (1)°	0.43 × 0.37 × 0.25 mm
β = 76.119 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8415 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7287 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.979	R_int = 0.019
31226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.59 e Å⁻³
8415 reflections	Δρ_min = −0.21 e Å⁻³
252 parameters

Special details top

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

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	0.34521 (6)	0.83032 (6)	0.99915 (5)	0.01579 (9)
O2	0.02841 (7)	1.17532 (6)	0.69020 (5)	0.02010 (11)
O3	−0.10300 (7)	0.70038 (7)	1.02725 (5)	0.02242 (11)
O4	0.16175 (7)	0.64603 (6)	0.49102 (5)	0.02133 (11)
C1	0.30785 (8)	0.95394 (7)	0.89677 (6)	0.01442 (11)
C2	0.42026 (8)	1.04139 (8)	0.85853 (6)	0.01674 (12)
H2A	0.5217	0.9742	0.8762	0.020*
H2B	0.3915	1.1068	0.9074	0.020*
C3	0.42656 (8)	1.13402 (7)	0.71914 (6)	0.01599 (11)
C4	0.26065 (9)	1.22259 (8)	0.69255 (7)	0.01843 (12)
H4A	0.2241	1.2977	0.7326	0.022*
H4B	0.2604	1.2733	0.6032	0.022*
C5	0.14947 (8)	1.13060 (7)	0.73661 (6)	0.01591 (11)
C6	0.18373 (8)	0.98961 (7)	0.83917 (6)	0.01459 (11)
C7	0.08188 (8)	0.88931 (7)	0.87495 (6)	0.01454 (11)
H7A	−0.0257	0.9474	0.8870	0.017*
C8	0.12303 (8)	0.76682 (7)	0.99633 (6)	0.01441 (11)
C9	0.02202 (8)	0.67001 (8)	1.06217 (6)	0.01635 (11)
C10	0.07186 (8)	0.53779 (8)	1.17715 (7)	0.01825 (12)
H10A	0.0404	0.4566	1.1776	0.022*
H10B	0.0174	0.5639	1.2507	0.022*
C11	0.24508 (8)	0.48275 (7)	1.18770 (6)	0.01565 (11)
C12	0.30063 (8)	0.61720 (7)	1.16306 (6)	0.01557 (11)
H12A	0.2626	0.6521	1.2341	0.019*
H12B	0.4122	0.5866	1.1551	0.019*
C13	0.24825 (8)	0.74137 (7)	1.04798 (6)	0.01417 (11)
C14	0.10119 (8)	0.82609 (7)	0.77113 (6)	0.01428 (11)
C15	−0.01107 (8)	0.87860 (7)	0.69164 (6)	0.01535 (11)
H15A	−0.1004	0.9526	0.7027	0.018*
C16	0.00783 (8)	0.82251 (7)	0.59602 (6)	0.01557 (11)
H16A	−0.0677	0.8601	0.5431	0.019*
C17	0.14000 (8)	0.70988 (7)	0.57955 (6)	0.01580 (11)
C18	0.25476 (8)	0.65753 (8)	0.65697 (7)	0.01858 (12)
H18A	0.3442	0.5839	0.6457	0.022*
C19	0.23478 (8)	0.71605 (8)	0.75134 (6)	0.01734 (12)
H19A	0.3120	0.6811	0.8023	0.021*
C20	0.50082 (11)	1.03502 (10)	0.63814 (8)	0.02510 (15)
H20A	0.5058	1.0956	0.5516	0.038*
H20B	0.4405	0.9697	0.6530	0.038*
H20C	0.6029	0.9775	0.6588	0.038*
C21	0.52047 (10)	1.24087 (8)	0.69189 (7)	0.02181 (14)
H21A	0.5222	1.3013	0.6053	0.033*
H21B	0.6238	1.1854	0.7104	0.033*
H21C	0.4745	1.3031	0.7429	0.033*
C22	0.33171 (9)	0.40175 (8)	1.09396 (7)	0.02121 (13)
H22A	0.2959	0.3178	1.1116	0.032*
H22B	0.4399	0.3687	1.1007	0.032*
H22C	0.3136	0.4680	1.0108	0.032*
C23	0.27504 (9)	0.37755 (8)	1.32038 (7)	0.02137 (13)
H23A	0.2417	0.2922	1.3380	0.032*
H23B	0.2191	0.4278	1.3792	0.032*
H23C	0.3831	0.3467	1.3271	0.032*
H1O4	0.0906 (19)	0.6959 (18)	0.4441 (15)	0.049 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0185 (2)	0.0151 (2)	0.0139 (2)	−0.00786 (17)	−0.00582 (16)	0.00009 (16)
O2	0.0238 (3)	0.0185 (2)	0.0186 (2)	−0.00527 (19)	−0.01005 (19)	−0.00298 (18)
O3	0.0192 (2)	0.0266 (3)	0.0221 (2)	−0.0106 (2)	−0.00590 (19)	−0.0033 (2)
O4	0.0263 (3)	0.0223 (2)	0.0170 (2)	−0.0028 (2)	−0.00794 (19)	−0.00877 (19)
C1	0.0185 (3)	0.0136 (2)	0.0116 (2)	−0.0058 (2)	−0.0037 (2)	−0.0025 (2)
C2	0.0210 (3)	0.0167 (3)	0.0145 (3)	−0.0092 (2)	−0.0052 (2)	−0.0022 (2)
C3	0.0206 (3)	0.0154 (3)	0.0131 (2)	−0.0077 (2)	−0.0017 (2)	−0.0040 (2)
C4	0.0225 (3)	0.0157 (3)	0.0155 (3)	−0.0072 (2)	−0.0050 (2)	−0.0005 (2)
C5	0.0208 (3)	0.0147 (2)	0.0126 (2)	−0.0050 (2)	−0.0049 (2)	−0.0034 (2)
C6	0.0178 (3)	0.0143 (2)	0.0121 (2)	−0.0057 (2)	−0.0042 (2)	−0.0026 (2)
C7	0.0156 (3)	0.0156 (2)	0.0129 (2)	−0.0051 (2)	−0.00397 (19)	−0.0033 (2)
C8	0.0163 (3)	0.0155 (2)	0.0119 (2)	−0.0062 (2)	−0.00282 (19)	−0.0031 (2)
C9	0.0173 (3)	0.0177 (3)	0.0148 (3)	−0.0072 (2)	−0.0019 (2)	−0.0044 (2)
C10	0.0176 (3)	0.0173 (3)	0.0177 (3)	−0.0072 (2)	−0.0021 (2)	−0.0018 (2)
C11	0.0175 (3)	0.0142 (2)	0.0152 (3)	−0.0060 (2)	−0.0028 (2)	−0.0032 (2)
C12	0.0195 (3)	0.0150 (2)	0.0128 (2)	−0.0070 (2)	−0.0047 (2)	−0.0018 (2)
C13	0.0169 (3)	0.0145 (2)	0.0121 (2)	−0.0066 (2)	−0.0024 (2)	−0.0032 (2)
C14	0.0157 (3)	0.0156 (2)	0.0125 (2)	−0.0058 (2)	−0.0036 (2)	−0.0034 (2)
C15	0.0158 (3)	0.0156 (2)	0.0150 (3)	−0.0046 (2)	−0.0048 (2)	−0.0036 (2)
C16	0.0176 (3)	0.0162 (3)	0.0137 (2)	−0.0059 (2)	−0.0055 (2)	−0.0027 (2)
C17	0.0197 (3)	0.0164 (3)	0.0120 (2)	−0.0065 (2)	−0.0035 (2)	−0.0033 (2)
C18	0.0182 (3)	0.0204 (3)	0.0161 (3)	−0.0019 (2)	−0.0052 (2)	−0.0065 (2)
C19	0.0164 (3)	0.0206 (3)	0.0151 (3)	−0.0035 (2)	−0.0051 (2)	−0.0057 (2)
C20	0.0305 (4)	0.0256 (3)	0.0223 (3)	−0.0114 (3)	0.0047 (3)	−0.0130 (3)
C21	0.0256 (3)	0.0196 (3)	0.0213 (3)	−0.0121 (3)	−0.0028 (3)	−0.0029 (3)
C22	0.0220 (3)	0.0194 (3)	0.0239 (3)	−0.0048 (2)	−0.0029 (3)	−0.0100 (3)
C23	0.0250 (3)	0.0172 (3)	0.0187 (3)	−0.0082 (2)	−0.0058 (2)	0.0011 (2)

Geometric parameters (Å, º) top

O1—C1	1.3680 (8)	C11—C22	1.5314 (10)
O1—C13	1.3798 (8)	C11—C23	1.5324 (10)
O2—C5	1.2348 (9)	C11—C12	1.5371 (9)
O3—C9	1.2273 (9)	C12—C13	1.4897 (9)
O4—C17	1.3658 (8)	C12—H12A	0.9700
O4—H1O4	0.851 (17)	C12—H12B	0.9700
C1—C6	1.3498 (9)	C14—C15	1.3931 (9)
C1—C2	1.4930 (9)	C14—C19	1.3974 (10)
C2—C3	1.5349 (9)	C15—C16	1.3922 (9)
C2—H2A	0.9700	C15—H15A	0.9300
C2—H2B	0.9700	C16—C17	1.3948 (10)
C3—C20	1.5272 (10)	C16—H16A	0.9300
C3—C21	1.5280 (10)	C17—C18	1.3950 (10)
C3—C4	1.5330 (10)	C18—C19	1.3934 (10)
C4—C5	1.5116 (10)	C18—H18A	0.9300
C4—H4A	0.9700	C19—H19A	0.9300
C4—H4B	0.9700	C20—H20A	0.9600
C5—C6	1.4628 (9)	C20—H20B	0.9600
C6—C7	1.5152 (9)	C20—H20C	0.9600
C7—C8	1.5096 (9)	C21—H21A	0.9600
C7—C14	1.5302 (9)	C21—H21B	0.9600
C7—H7A	0.9800	C21—H21C	0.9600
C8—C13	1.3445 (9)	C22—H22A	0.9600
C8—C9	1.4773 (9)	C22—H22B	0.9600
C9—C10	1.5177 (10)	C22—H22C	0.9600
C10—C11	1.5354 (10)	C23—H23A	0.9600
C10—H10A	0.9700	C23—H23B	0.9600
C10—H10B	0.9700	C23—H23C	0.9600

C1—O1—C13	118.25 (5)	C10—C11—C12	108.40 (6)
C17—O4—H1O4	108.2 (11)	C13—C12—C11	112.63 (5)
C6—C1—O1	122.95 (6)	C13—C12—H12A	109.1
C6—C1—C2	125.29 (6)	C11—C12—H12A	109.1
O1—C1—C2	111.76 (5)	C13—C12—H12B	109.1
C1—C2—C3	112.06 (5)	C11—C12—H12B	109.1
C1—C2—H2A	109.2	H12A—C12—H12B	107.8
C3—C2—H2A	109.2	C8—C13—O1	123.08 (6)
C1—C2—H2B	109.2	C8—C13—C12	125.63 (6)
C3—C2—H2B	109.2	O1—C13—C12	111.29 (5)
H2A—C2—H2B	107.9	C15—C14—C19	118.00 (6)
C20—C3—C21	109.14 (6)	C15—C14—C7	121.39 (6)
C20—C3—C4	110.88 (6)	C19—C14—C7	120.59 (6)
C21—C3—C4	109.50 (6)	C16—C15—C14	121.28 (6)
C20—C3—C2	111.08 (6)	C16—C15—H15A	119.4
C21—C3—C2	109.08 (6)	C14—C15—H15A	119.4
C4—C3—C2	107.12 (6)	C15—C16—C17	120.04 (6)
C5—C4—C3	114.58 (6)	C15—C16—H16A	120.0
C5—C4—H4A	108.6	C17—C16—H16A	120.0
C3—C4—H4A	108.6	O4—C17—C16	122.64 (6)
C5—C4—H4B	108.6	O4—C17—C18	117.87 (6)
C3—C4—H4B	108.6	C16—C17—C18	119.48 (6)
H4A—C4—H4B	107.6	C19—C18—C17	119.72 (7)
O2—C5—C6	119.90 (6)	C19—C18—H18A	120.1
O2—C5—C4	120.92 (6)	C17—C18—H18A	120.1
C6—C5—C4	119.14 (6)	C18—C19—C14	121.44 (6)
C1—C6—C5	117.69 (6)	C18—C19—H19A	119.3
C1—C6—C7	122.86 (6)	C14—C19—H19A	119.3
C5—C6—C7	119.44 (6)	C3—C20—H20A	109.5
C8—C7—C6	108.86 (5)	C3—C20—H20B	109.5
C8—C7—C14	111.06 (5)	H20A—C20—H20B	109.5
C6—C7—C14	110.30 (5)	C3—C20—H20C	109.5
C8—C7—H7A	108.9	H20A—C20—H20C	109.5
C6—C7—H7A	108.9	H20B—C20—H20C	109.5
C14—C7—H7A	108.9	C3—C21—H21A	109.5
C13—C8—C9	118.04 (6)	C3—C21—H21B	109.5
C13—C8—C7	122.91 (6)	H21A—C21—H21B	109.5
C9—C8—C7	119.05 (6)	C3—C21—H21C	109.5
O3—C9—C8	120.20 (6)	H21A—C21—H21C	109.5
O3—C9—C10	120.86 (6)	H21B—C21—H21C	109.5
C8—C9—C10	118.87 (6)	C11—C22—H22A	109.5
C9—C10—C11	115.38 (6)	C11—C22—H22B	109.5
C9—C10—H10A	108.4	H22A—C22—H22B	109.5
C11—C10—H10A	108.4	C11—C22—H22C	109.5
C9—C10—H10B	108.4	H22A—C22—H22C	109.5
C11—C10—H10B	108.4	H22B—C22—H22C	109.5
H10A—C10—H10B	107.5	C11—C23—H23A	109.5
C22—C11—C23	109.53 (6)	C11—C23—H23B	109.5
C22—C11—C10	110.09 (6)	H23A—C23—H23B	109.5
C23—C11—C10	110.01 (6)	C11—C23—H23C	109.5
C22—C11—C12	110.94 (6)	H23A—C23—H23C	109.5
C23—C11—C12	107.83 (5)	H23B—C23—H23C	109.5

C13—O1—C1—C6	−2.38 (10)	C7—C8—C9—C10	174.00 (6)
C13—O1—C1—C2	177.69 (6)	O3—C9—C10—C11	161.59 (7)
C6—C1—C2—C3	−25.58 (10)	C8—C9—C10—C11	−21.61 (9)
O1—C1—C2—C3	154.34 (6)	C9—C10—C11—C22	−73.51 (7)
C1—C2—C3—C20	−69.86 (8)	C9—C10—C11—C23	165.69 (6)
C1—C2—C3—C21	169.79 (6)	C9—C10—C11—C12	48.00 (8)
C1—C2—C3—C4	51.36 (7)	C22—C11—C12—C13	72.05 (7)
C20—C3—C4—C5	69.49 (8)	C23—C11—C12—C13	−168.01 (6)
C21—C3—C4—C5	−170.02 (6)	C10—C11—C12—C13	−48.94 (7)
C2—C3—C4—C5	−51.86 (7)	C9—C8—C13—O1	−175.73 (6)
C3—C4—C5—O2	−157.76 (6)	C7—C8—C13—O1	4.22 (10)
C3—C4—C5—C6	24.75 (9)	C9—C8—C13—C12	4.00 (10)
O1—C1—C6—C5	175.35 (6)	C7—C8—C13—C12	−176.05 (6)
C2—C1—C6—C5	−4.74 (10)	C1—O1—C13—C8	3.14 (10)
O1—C1—C6—C7	−5.68 (10)	C1—O1—C13—C12	−176.62 (5)
C2—C1—C6—C7	174.24 (6)	C11—C12—C13—C8	25.26 (9)
O2—C5—C6—C1	−172.19 (6)	C11—C12—C13—O1	−154.98 (6)
C4—C5—C6—C1	5.34 (9)	C8—C7—C14—C15	134.11 (6)
O2—C5—C6—C7	8.80 (10)	C6—C7—C14—C15	−105.11 (7)
C4—C5—C6—C7	−173.67 (6)	C8—C7—C14—C19	−47.61 (8)
C1—C6—C7—C8	11.35 (9)	C6—C7—C14—C19	73.17 (8)
C5—C6—C7—C8	−169.70 (6)	C19—C14—C15—C16	0.67 (10)
C1—C6—C7—C14	−110.74 (7)	C7—C14—C15—C16	178.99 (6)
C5—C6—C7—C14	68.21 (8)	C14—C15—C16—C17	1.03 (10)
C6—C7—C8—C13	−10.62 (9)	C15—C16—C17—O4	177.02 (6)
C14—C7—C8—C13	111.01 (7)	C15—C16—C17—C18	−2.02 (10)
C6—C7—C8—C9	169.33 (6)	O4—C17—C18—C19	−177.79 (6)
C14—C7—C8—C9	−69.04 (8)	C16—C17—C18—C19	1.30 (11)
C13—C8—C9—O3	170.78 (7)	C17—C18—C19—C14	0.43 (11)
C7—C8—C9—O3	−9.17 (10)	C15—C14—C19—C18	−1.40 (10)
C13—C8—C9—C10	−6.04 (9)	C7—C14—C19—C18	−179.74 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O2ⁱ	0.851 (18)	1.910 (17)	2.7423 (9)	165.6 (17)

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆O₄
M_r	366.44
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3525 (1), 10.2140 (1), 11.6913 (1)
α, β, γ (°)	67.271 (1), 76.119 (1), 69.419 (1)
V (Å³)	957.32 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.37 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.964, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	31226, 8415, 7287
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.811

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.119, 1.05
No. of reflections	8415
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.21

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
O4—H1O4···O2ⁱ	0.851 (18)	1.910 (17)	2.7423 (9)	165.6 (17)

Symmetry code: (i) −x, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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