1-(4-Meth­oxy­phen­yl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxyl­ate

Fun, H.-K.; Quah, C.K.; Wu, D.

doi:10.1107/S160053681201848X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1628

doi:10.1107/S160053681201848X

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1-(4-Methoxyphenyl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah ^a § and Dongdong Wu ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 20 April 2012; accepted 25 April 2012; online 5 May 2012)

In the title molecule, C₂₃H₁₈O₅, the methoxy-substituted benzene ring makes dihedral angles of 65.12 (4) and 88.55 (4)° with the other two benzene rings. These two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, molecules are linked into inversion dimers by pairs of weak C—H⋯O hydrogen bonds.

Related literature

For the background to this study has been set out in the preceding paper, see: Fun et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For standard bond-length data, see: Allen et al. (1987 ). For the preparation, see: Wu et al. (2012 ).

Experimental

Crystal data

C₂₃H₁₈O₅
M_r = 374.37
Monoclinic, P 2₁ /c
a = 14.0049 (5) Å
b = 10.8637 (4) Å
c = 12.7190 (5) Å
β = 110.150 (1)°
V = 1816.69 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.50 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.969
30595 measured reflections
8040 independent reflections
6872 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.122
S = 1.03
8040 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O3ⁱ	0.98	2.60	3.2676 (10)	126
Symmetry code: (i) -x+1, -y+1, -z.

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/S160053681201848X/is5123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201848X/is5123Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201848X/is5123Isup3.cml

checkCIF report

Comment top

The title compound belongs to the biphenyl-containing bislactone family whose preparation could be achieved through a concise photochemical method (Wu et al., 2012). In the title compound, Fig. 1, the methoxy attached phenyl ring (C17–C22) inclines at dihedral angles of 65.12 (4) and 88.55 (4)° with the two benzene rings (C2–C7 and C8–C13), respectively. The two benzene rings form a dihedral angle of 45.70 (4)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Fun et al., 2012). In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C16—H16A···O3 hydrogen bonds (Table 1).

Related literature top

For the background to this study has been set out in the preceding paper, see: Fun et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For the preparation, see: Wu et al. (2012).

Experimental top

The title compound was the major diastereoisomer of the sequential photoreaction products of 9,10-phenanthrenedione with 1-methoxy-4-vinylbenzene. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:9) as eluents. X-ray quality crystals of the title compound were obtained from slow evaporation of an acetone and petroleum ether solution (1:10).

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.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-(4-Methoxyphenyl)ethane-1,2-diyl 1,1'-biphenyl-2,2'-dicarboxylate top

Crystal data top

C₂₃H₁₈O₅	F(000) = 784
M_r = 374.37	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9888 reflections
a = 14.0049 (5) Å	θ = 3.3–35.1°
b = 10.8637 (4) Å	µ = 0.10 mm⁻¹
c = 12.7190 (5) Å	T = 100 K
β = 110.150 (1)°	Block, colourless
V = 1816.69 (12) Å³	0.50 × 0.37 × 0.33 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	8040 independent reflections
Radiation source: fine-focus sealed tube	6872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 35.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
T_min = 0.954, T_max = 0.969	k = −17→16
30595 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0706P)² + 0.3453P] where P = (F_o² + 2F_c²)/3
8040 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₈O₅	V = 1816.69 (12) Å³
M_r = 374.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0049 (5) Å	µ = 0.10 mm⁻¹
b = 10.8637 (4) Å	T = 100 K
c = 12.7190 (5) Å	0.50 × 0.37 × 0.33 mm
β = 110.150 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	8040 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6872 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.969	R_int = 0.025
30595 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.03	Δρ_max = 0.52 e Å⁻³
8040 reflections	Δρ_min = −0.23 e Å⁻³
254 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 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 > 2sigma(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	0.38784 (4)	0.55150 (5)	0.14424 (4)	0.01591 (10)
O2	0.35057 (4)	0.34260 (5)	0.01861 (5)	0.01878 (11)
O3	0.35878 (4)	0.61128 (5)	−0.03585 (5)	0.01878 (11)
O4	0.23791 (5)	0.35189 (5)	0.11150 (5)	0.02007 (11)
O5	0.77642 (5)	0.51575 (6)	0.57884 (5)	0.02188 (12)
C1	0.33248 (5)	0.60283 (6)	0.04471 (6)	0.01410 (11)
C2	0.23425 (5)	0.64784 (6)	0.05242 (6)	0.01326 (11)
C3	0.24048 (5)	0.74160 (6)	0.12951 (6)	0.01596 (12)
H3A	0.3038	0.7721	0.1731	0.019*
C4	0.15308 (6)	0.78980 (7)	0.14184 (7)	0.01838 (13)
H4A	0.1576	0.8539	0.1918	0.022*
C5	0.05903 (6)	0.74156 (7)	0.07911 (7)	0.01791 (13)
H5A	0.0002	0.7724	0.0877	0.021*
C6	0.05267 (5)	0.64697 (6)	0.00326 (6)	0.01502 (12)
H6A	−0.0108	0.6148	−0.0377	0.018*
C7	0.13932 (5)	0.59887 (6)	−0.01318 (6)	0.01314 (11)
C8	0.12481 (5)	0.50195 (6)	−0.10053 (6)	0.01377 (11)
C9	0.04937 (5)	0.52047 (7)	−0.20515 (6)	0.01666 (12)
H9A	0.0091	0.5907	−0.2169	0.020*
C10	0.03313 (6)	0.43626 (7)	−0.29216 (6)	0.01981 (13)
H10A	−0.0186	0.4495	−0.3604	0.024*
C11	0.09433 (6)	0.33242 (7)	−0.27690 (7)	0.02003 (13)
H11A	0.0852	0.2775	−0.3356	0.024*
C12	0.16915 (6)	0.31098 (7)	−0.17363 (7)	0.01812 (13)
H12A	0.2103	0.2416	−0.1633	0.022*
C13	0.18276 (5)	0.39331 (6)	−0.08526 (6)	0.01456 (11)
C14	0.25758 (6)	0.36052 (6)	0.02653 (6)	0.01598 (12)
C15	0.43566 (6)	0.34300 (7)	0.12253 (7)	0.02087 (14)
H15A	0.4893	0.2904	0.1161	0.025*
H15B	0.4146	0.3116	0.1825	0.025*
C16	0.47489 (5)	0.47470 (7)	0.14896 (6)	0.01735 (12)
H16A	0.5039	0.5029	0.0932	0.021*
C17	0.55272 (5)	0.48569 (7)	0.26440 (6)	0.01667 (12)
C18	0.53402 (6)	0.43948 (8)	0.35776 (7)	0.02047 (14)
H18A	0.4718	0.4023	0.3484	0.025*
C19	0.60657 (6)	0.44787 (8)	0.46475 (6)	0.01999 (13)
H19A	0.5933	0.4160	0.5262	0.024*
C20	0.69930 (5)	0.50455 (7)	0.47858 (6)	0.01664 (12)
C21	0.71830 (6)	0.55306 (6)	0.38612 (6)	0.01783 (13)
H21A	0.7798	0.5922	0.3957	0.021*
C22	0.64573 (6)	0.54311 (6)	0.28016 (6)	0.01736 (12)
H22A	0.6591	0.5750	0.2188	0.021*
C23	0.76498 (7)	0.45148 (10)	0.67193 (7)	0.02796 (18)
H23A	0.8262	0.4595	0.7357	0.042*
H23B	0.7521	0.3660	0.6533	0.042*
H23C	0.7089	0.4858	0.6892	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0142 (2)	0.0186 (2)	0.0154 (2)	0.00415 (17)	0.00568 (17)	0.00102 (17)
O2	0.0156 (2)	0.0204 (2)	0.0190 (2)	0.00381 (18)	0.00424 (18)	−0.00265 (18)
O3	0.0179 (2)	0.0224 (2)	0.0184 (2)	0.00192 (19)	0.00934 (19)	0.00145 (19)
O4	0.0244 (3)	0.0174 (2)	0.0200 (2)	0.00093 (19)	0.0096 (2)	0.00254 (18)
O5	0.0199 (3)	0.0270 (3)	0.0163 (2)	−0.0030 (2)	0.0032 (2)	−0.0001 (2)
C1	0.0129 (3)	0.0133 (2)	0.0162 (3)	0.0003 (2)	0.0052 (2)	−0.0004 (2)
C2	0.0133 (3)	0.0122 (2)	0.0153 (3)	0.00065 (19)	0.0062 (2)	0.00129 (19)
C3	0.0164 (3)	0.0141 (2)	0.0187 (3)	−0.0004 (2)	0.0078 (2)	−0.0016 (2)
C4	0.0202 (3)	0.0152 (3)	0.0227 (3)	0.0006 (2)	0.0112 (3)	−0.0023 (2)
C5	0.0175 (3)	0.0165 (3)	0.0229 (3)	0.0027 (2)	0.0110 (2)	0.0014 (2)
C6	0.0137 (3)	0.0149 (2)	0.0179 (3)	0.0014 (2)	0.0072 (2)	0.0027 (2)
C7	0.0135 (3)	0.0124 (2)	0.0144 (3)	0.00076 (19)	0.0058 (2)	0.00167 (19)
C8	0.0134 (3)	0.0141 (2)	0.0148 (3)	−0.00113 (19)	0.0061 (2)	0.0003 (2)
C9	0.0153 (3)	0.0190 (3)	0.0154 (3)	−0.0012 (2)	0.0049 (2)	0.0015 (2)
C10	0.0185 (3)	0.0242 (3)	0.0160 (3)	−0.0055 (2)	0.0050 (2)	−0.0011 (2)
C11	0.0206 (3)	0.0215 (3)	0.0189 (3)	−0.0072 (2)	0.0080 (3)	−0.0057 (2)
C12	0.0185 (3)	0.0157 (3)	0.0213 (3)	−0.0028 (2)	0.0084 (2)	−0.0038 (2)
C13	0.0143 (3)	0.0137 (2)	0.0163 (3)	−0.0012 (2)	0.0061 (2)	−0.0007 (2)
C14	0.0170 (3)	0.0120 (2)	0.0189 (3)	0.0012 (2)	0.0062 (2)	−0.0005 (2)
C15	0.0183 (3)	0.0196 (3)	0.0211 (3)	0.0057 (2)	0.0022 (3)	−0.0017 (2)
C16	0.0142 (3)	0.0214 (3)	0.0165 (3)	0.0049 (2)	0.0053 (2)	−0.0004 (2)
C17	0.0143 (3)	0.0199 (3)	0.0160 (3)	0.0029 (2)	0.0054 (2)	0.0003 (2)
C18	0.0143 (3)	0.0304 (4)	0.0174 (3)	−0.0009 (3)	0.0065 (2)	0.0002 (3)
C19	0.0170 (3)	0.0284 (3)	0.0159 (3)	−0.0006 (3)	0.0074 (2)	0.0004 (2)
C20	0.0160 (3)	0.0176 (3)	0.0159 (3)	0.0011 (2)	0.0048 (2)	−0.0010 (2)
C21	0.0181 (3)	0.0161 (3)	0.0193 (3)	−0.0016 (2)	0.0065 (2)	0.0001 (2)
C22	0.0188 (3)	0.0163 (3)	0.0176 (3)	0.0010 (2)	0.0071 (2)	0.0018 (2)
C23	0.0225 (4)	0.0423 (5)	0.0169 (3)	−0.0023 (3)	0.0040 (3)	0.0039 (3)

Geometric parameters (Å, º) top

O1—C1	1.3558 (9)	C10—H10A	0.9300
O1—C16	1.4613 (9)	C11—C12	1.3890 (11)
O2—C14	1.3543 (9)	C11—H11A	0.9300
O2—C15	1.4429 (9)	C12—C13	1.3971 (10)
O3—C1	1.2058 (9)	C12—H12A	0.9300
O4—C14	1.2073 (9)	C13—C14	1.4901 (10)
O5—C20	1.3633 (9)	C15—C16	1.5281 (11)
O5—C23	1.4303 (11)	C15—H15A	0.9700
C1—C2	1.4948 (9)	C15—H15B	0.9700
C2—C3	1.3955 (10)	C16—C17	1.5019 (10)
C2—C7	1.4080 (9)	C16—H16A	0.9800
C3—C4	1.3891 (10)	C17—C18	1.3946 (11)
C3—H3A	0.9300	C17—C22	1.3950 (10)
C4—C5	1.3864 (11)	C18—C19	1.3928 (11)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.3913 (10)	C19—C20	1.3925 (11)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.4016 (9)	C20—C21	1.3954 (11)
C6—H6A	0.9300	C21—C22	1.3846 (10)
C7—C8	1.4928 (10)	C21—H21A	0.9300
C8—C9	1.3995 (10)	C22—H22A	0.9300
C8—C13	1.4074 (10)	C23—H23A	0.9600
C9—C10	1.3929 (11)	C23—H23B	0.9600
C9—H9A	0.9300	C23—H23C	0.9600
C10—C11	1.3893 (12)

C1—O1—C16	118.28 (6)	C8—C13—C14	120.98 (6)
C14—O2—C15	116.31 (6)	O4—C14—O2	125.25 (7)
C20—O5—C23	116.88 (6)	O4—C14—C13	124.78 (7)
O3—C1—O1	125.52 (6)	O2—C14—C13	109.97 (6)
O3—C1—C2	126.03 (6)	O2—C15—C16	108.98 (6)
O1—C1—C2	108.45 (6)	O2—C15—H15A	109.9
C3—C2—C7	120.66 (6)	C16—C15—H15A	109.9
C3—C2—C1	116.65 (6)	O2—C15—H15B	109.9
C7—C2—C1	122.68 (6)	C16—C15—H15B	109.9
C4—C3—C2	120.67 (7)	H15A—C15—H15B	108.3
C4—C3—H3A	119.7	O1—C16—C17	108.00 (6)
C2—C3—H3A	119.7	O1—C16—C15	107.09 (6)
C5—C4—C3	119.48 (7)	C17—C16—C15	111.98 (6)
C5—C4—H4A	120.3	O1—C16—H16A	109.9
C3—C4—H4A	120.3	C17—C16—H16A	109.9
C4—C5—C6	119.97 (7)	C15—C16—H16A	109.9
C4—C5—H5A	120.0	C18—C17—C22	118.59 (7)
C6—C5—H5A	120.0	C18—C17—C16	121.19 (7)
C5—C6—C7	121.80 (7)	C22—C17—C16	120.22 (7)
C5—C6—H6A	119.1	C19—C18—C17	121.36 (7)
C7—C6—H6A	119.1	C19—C18—H18A	119.3
C6—C7—C2	117.39 (6)	C17—C18—H18A	119.3
C6—C7—C8	118.10 (6)	C20—C19—C18	119.15 (7)
C2—C7—C8	124.49 (6)	C20—C19—H19A	120.4
C9—C8—C13	117.54 (6)	C18—C19—H19A	120.4
C9—C8—C7	118.09 (6)	O5—C20—C19	124.16 (7)
C13—C8—C7	124.37 (6)	O5—C20—C21	115.78 (7)
C10—C9—C8	121.61 (7)	C19—C20—C21	120.06 (7)
C10—C9—H9A	119.2	C22—C21—C20	120.11 (7)
C8—C9—H9A	119.2	C22—C21—H21A	119.9
C11—C10—C9	119.89 (7)	C20—C21—H21A	119.9
C11—C10—H10A	120.1	C21—C22—C17	120.71 (7)
C9—C10—H10A	120.1	C21—C22—H22A	119.6
C12—C11—C10	119.76 (7)	C17—C22—H22A	119.6
C12—C11—H11A	120.1	O5—C23—H23A	109.5
C10—C11—H11A	120.1	O5—C23—H23B	109.5
C11—C12—C13	120.18 (7)	H23A—C23—H23B	109.5
C11—C12—H12A	119.9	O5—C23—H23C	109.5
C13—C12—H12A	119.9	H23A—C23—H23C	109.5
C12—C13—C8	120.90 (6)	H23B—C23—H23C	109.5
C12—C13—C14	118.09 (6)

C16—O1—C1—O3	−15.26 (10)	C9—C8—C13—C14	−174.01 (6)
C16—O1—C1—C2	165.24 (6)	C7—C8—C13—C14	6.70 (10)
O3—C1—C2—C3	−115.76 (8)	C15—O2—C14—O4	−15.77 (10)
O1—C1—C2—C3	63.74 (8)	C15—O2—C14—C13	163.90 (6)
O3—C1—C2—C7	64.78 (10)	C12—C13—C14—O4	−122.73 (8)
O1—C1—C2—C7	−115.72 (7)	C8—C13—C14—O4	55.03 (10)
C7—C2—C3—C4	−1.00 (10)	C12—C13—C14—O2	57.60 (8)
C1—C2—C3—C4	179.52 (6)	C8—C13—C14—O2	−124.64 (7)
C2—C3—C4—C5	1.90 (11)	C14—O2—C15—C16	−89.13 (8)
C3—C4—C5—C6	−1.03 (11)	C1—O1—C16—C17	149.64 (6)
C4—C5—C6—C7	−0.75 (11)	C1—O1—C16—C15	−89.59 (7)
C5—C6—C7—C2	1.62 (10)	O2—C15—C16—O1	52.88 (8)
C5—C6—C7—C8	−176.89 (6)	O2—C15—C16—C17	171.09 (6)
C3—C2—C7—C6	−0.74 (10)	O1—C16—C17—C18	66.97 (9)
C1—C2—C7—C6	178.70 (6)	C15—C16—C17—C18	−50.70 (9)
C3—C2—C7—C8	177.67 (6)	O1—C16—C17—C22	−112.89 (7)
C1—C2—C7—C8	−2.89 (10)	C15—C16—C17—C22	129.45 (7)
C6—C7—C8—C9	45.82 (9)	C22—C17—C18—C19	−1.10 (12)
C2—C7—C8—C9	−132.57 (7)	C16—C17—C18—C19	179.04 (7)
C6—C7—C8—C13	−134.90 (7)	C17—C18—C19—C20	0.54 (12)
C2—C7—C8—C13	46.71 (10)	C23—O5—C20—C19	8.11 (11)
C13—C8—C9—C10	−1.31 (10)	C23—O5—C20—C21	−171.16 (7)
C7—C8—C9—C10	178.02 (6)	C18—C19—C20—O5	−178.66 (7)
C8—C9—C10—C11	−1.62 (11)	C18—C19—C20—C21	0.58 (12)
C9—C10—C11—C12	2.22 (11)	O5—C20—C21—C22	178.19 (7)
C10—C11—C12—C13	0.14 (11)	C19—C20—C21—C22	−1.11 (11)
C11—C12—C13—C8	−3.16 (11)	C20—C21—C22—C17	0.54 (11)
C11—C12—C13—C14	174.61 (7)	C18—C17—C22—C21	0.55 (11)
C9—C8—C13—C12	3.69 (10)	C16—C17—C22—C21	−179.59 (6)
C7—C8—C13—C12	−175.60 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3ⁱ	0.98	2.60	3.2676 (10)	126

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈O₅
M_r	374.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.0049 (5), 10.8637 (4), 12.7190 (5)
β (°)	110.150 (1)
V (Å³)	1816.69 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.37 × 0.33

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	30595, 8040, 6872
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.810

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.03
No. of reflections	8040
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.23

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
C16—H16A···O3ⁱ	0.98	2.60	3.2676 (10)	126

Symmetry code: (i) −x+1, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Natural Science Foundation of China (20972067) is acknowledged.

References

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