2-(4-{4-[4-(Oxiran-2-ylmeth­oxy)phen­oxy]phen­yl}phen­oxy­meth­yl)oxirane

Song, T.; Liu, J.; Yang, S.

doi:10.1107/S1600536812005740

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o719

doi:10.1107/S1600536812005740

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2-(4-{4-[4-(Oxiran-2-ylmethoxy)phenoxy]phenyl}phenoxymethyl)oxirane

Tao Song,^a Jin-gang Liu ^a ^* and Shi-yong Yang ^a ^*

^aLaboratory of Advanced Polymer Materials, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), Beijing 100190, People's Republic of China
^*Correspondence e-mail: liujg@iccas.ac.cn, shiyang@iccas.ac.cn

(Received 8 February 2012; accepted 9 February 2012; online 17 February 2012)

In the title epoxy monomer, C₂₄H₂₂O₅, the dihedral angle in the biphenyl residue is 3.34 (19)°, indicating a nearly coplanar conformation; this residue is not planar with the adjacent benzene ring [dihedral angle = 58.93 (14)°]. Each of the epoxide rings is disordered. Each epoxide ring was resolved over two alternative positions with site-occupancy ratios of 0.638 (10):0.362 (10) and 0.797 (9):0.203 (9).

Related literature

For micro-electronic applications of biphenyl-type epoxy compounds, see: Lee & Neville (1990 ); Yoda (1997 ); Kim & Lee (2002 ). For related structures, see: Cho et al. (1999 ); Flippen-Anderson & Gilardi (1981 ).

Experimental

Crystal data

C₂₄H₂₂O₅
M_r = 390.42
Monoclinic, P c
a = 21.261 (4) Å
b = 7.3103 (15) Å
c = 6.1322 (12) Å
β = 93.59 (3)°
V = 951.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.35 × 0.15 × 0.08 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.983, T_max = 0.992
6607 measured reflections
1965 independent reflections
1728 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.172
S = 1.18
1965 reflections
318 parameters
264 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005740/tk5057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005740/tk5057Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005740/tk5057Isup3.cml

checkCIF report

Comment top

The title compound can be used as matrix for epoxy coating, paintings, composites and adhesives (Lee & Neville, 1990). Especially, this compound is a very useful component for advanced epoxy molding compounds (EMCs) for microelectronic packaging. The asymmetric crystalline nature of the title epoxy compound endows the obtained EMCs with very low melting viscosity, thus providing good flow-ability during molding process (Kim & Lee, 2002). Good flow-ability of the EMCs is crucial for the packaging of thin type microelectronic devices (Yoda, 1997).

The title compound has an asymmetrical structure. The dihedral angle between the benzene ring (C16—C21) and the biphenyl ring is 58.93 (14)°. The dihedral angle in the biphenyl moiety is 3.34 (19)°, indicating a essentially co-planar conformation.

As can be seen from Fig. 1, the epoxide rings in molecule (I) are locally disordered. The two disordered residues consist of two alternative orientations for the epoxide rings connected to C3 and C22, respectively. Such disorder for epoxide rings has been noted in the literature (Cho et al., 1999; Flippen-Anderson & Gilardi, 1981).

Related literature top

For micro-electronic applications of biphenyl-type epoxy compounds, see: Lee & Neville (1990); Yoda (1997); Kim & Lee (2002). For related structures, see: Cho et al. (1999); Flippen-Anderson & Gilardi (1981).

Experimental top

4-(p-Hydroxyphenoxy)-4'-hydroxybiphenyl (27.8 g, 0.1 mol), epichlorohydrin (222 g, 2.4 mol), and the phase transfer agent, benzyltrimethylammonium chloride (BTMAC, 0.216 g, 1 mmol) were put into a 250 ml four-necked flask equipped with a stirrer, a drop funnel, a condenser, and a thermometer. The reaction mixture was then heated to reflux for 60 min. until a homogeneous solution formed. An aqueous solution of NaOH (45 wt%, 20 g) was added drop wise over 3 h at 333 K. Then, the reaction was heated under reflux for 2 h and cooled to room temperature. The obtained white precipitate was filtered, washed with deionized water and dried in vacuo at 353 K overnight. The white crystalline powder was further purified by recrystallization from acetonitrile to afford the title compound (29.2 g, 75% yield). Elemental analysis: calculated for C₂₄H₂₂O₅: C, 73.83; H, 5.68%. Found: C, 73.73; H, 5.69%. EI—MS, m/z: 390(100, M⁺). Colourless crystals were grown by slow evaporation of an acetone-diethyl ether solution (1:3, volume ratio) over a period of several days, M.pt:. 438 K.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown. The atoms labelled with a prime correspond to the minor components of the disordered residues.

2-(4-{4-[4-(Oxiran-2-ylmethoxy)phenoxy]phenyl}phenoxymethyl)oxirane top

Crystal data top

C₂₄H₂₂O₅	F(000) = 412
M_r = 390.42	D_x = 1.363 Mg m⁻³
Monoclinic, Pc	Melting point: 438 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.261 (4) Å	Cell parameters from 2903 reflections
b = 7.3103 (15) Å	θ = 1.9–27.4°
c = 6.1322 (12) Å	µ = 0.10 mm⁻¹
β = 93.59 (3)°	T = 173 K
V = 951.2 (3) Å³	Rod, colourless
Z = 2	0.35 × 0.15 × 0.08 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	1965 independent reflections
Radiation source: fine-focus sealed tube	1728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 28.5714 pixels mm^-1	θ_max = 26.5°, θ_min = 2.8°
ω scans at fixed χ = 45°	h = −26→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −9→8
T_min = 0.983, T_max = 0.992	l = −6→7
6607 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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0442P)² + 0.969P] where P = (F_o² + 2F_c²)/3
1965 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.23 e Å⁻³
264 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₂₂O₅	V = 951.2 (3) Å³
M_r = 390.42	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 21.261 (4) Å	µ = 0.10 mm⁻¹
b = 7.3103 (15) Å	T = 173 K
c = 6.1322 (12) Å	0.35 × 0.15 × 0.08 mm
β = 93.59 (3)°

Data collection top

Rigaku Saturn724+ CCD diffractometer	1965 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	1728 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.992	R_int = 0.065
6607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	264 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.18	Δρ_max = 0.23 e Å⁻³
1965 reflections	Δρ_min = −0.19 e Å⁻³
318 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	Occ. (<1)
O2	0.9679 (2)	0.7379 (6)	0.1402 (7)	0.0392 (11)
O3	0.54379 (19)	0.7479 (6)	−0.6168 (6)	0.0332 (10)
O4	0.3068 (2)	0.7607 (6)	−0.2978 (7)	0.0410 (11)
O1	1.0723 (6)	0.8198 (13)	0.6156 (15)	0.061 (2)	0.638 (10)
C1	1.0717 (6)	0.6394 (13)	0.5111 (18)	0.060 (2)	0.638 (10)
H1B	1.1127	0.5836	0.4810	0.072*	0.638 (10)
H1A	1.0386	0.5516	0.5492	0.072*	0.638 (10)
C2	1.0523 (4)	0.7999 (16)	0.3903 (17)	0.055 (2)	0.638 (10)
H2	1.0802	0.8476	0.2777	0.066*	0.638 (10)
O1'	1.0674 (10)	0.770 (3)	0.653 (2)	0.060 (3)	0.362 (10)
C1'	1.0982 (9)	0.767 (3)	0.449 (3)	0.059 (3)	0.362 (10)
H1'B	1.1318	0.6756	0.4321	0.070*	0.362 (10)
H1'A	1.1042	0.8853	0.3743	0.070*	0.362 (10)
C2'	1.0322 (7)	0.700 (2)	0.466 (3)	0.058 (3)	0.362 (10)
H2'	1.0254	0.5642	0.4592	0.070*	0.362 (10)
C3	0.9816 (3)	0.8206 (11)	0.3504 (11)	0.0502 (19)
H3A	0.9591	0.7566	0.4646	0.060*
H3B	0.9692	0.9512	0.3485	0.060*
C4	0.9072 (2)	0.7504 (8)	0.0492 (9)	0.0279 (13)
C5	0.8585 (3)	0.8380 (8)	0.1427 (9)	0.0354 (15)
H5	0.8656	0.8995	0.2784	0.042*
C6	0.7988 (3)	0.8361 (8)	0.0377 (9)	0.0346 (14)
H6	0.7654	0.8960	0.1051	0.041*
C7	0.7856 (3)	0.7487 (8)	−0.1651 (9)	0.0267 (12)
C8	0.8369 (3)	0.6606 (8)	−0.2527 (9)	0.0317 (14)
H8	0.8308	0.5998	−0.3893	0.038*
C9	0.8956 (3)	0.6597 (8)	−0.1472 (9)	0.0300 (13)
H9	0.9289	0.5957	−0.2098	0.036*
C10	0.7221 (3)	0.7498 (7)	−0.2772 (9)	0.0263 (12)
C11	0.6702 (3)	0.8303 (8)	−0.1862 (9)	0.0336 (14)
H11	0.6764	0.8877	−0.0475	0.040*
C12	0.6101 (3)	0.8307 (8)	−0.2881 (10)	0.0343 (14)
H12	0.5760	0.8871	−0.2209	0.041*
C13	0.6008 (3)	0.7464 (8)	−0.4914 (9)	0.0313 (14)
C14	0.6509 (3)	0.6685 (8)	−0.5893 (9)	0.0299 (13)
H14	0.6449	0.6136	−0.7295	0.036*
C15	0.7100 (3)	0.6714 (8)	−0.4809 (9)	0.0315 (13)
H15	0.7441	0.6166	−0.5500	0.038*
C16	0.4871 (3)	0.7515 (8)	−0.5173 (9)	0.0294 (13)
C17	0.4759 (3)	0.6561 (8)	−0.3279 (9)	0.0292 (12)
H17	0.5092	0.5914	−0.2517	0.035*
C18	0.4161 (3)	0.6554 (8)	−0.2499 (10)	0.0370 (14)
H18	0.4082	0.5906	−0.1202	0.044*
C19	0.3672 (3)	0.7514 (8)	−0.3645 (9)	0.0311 (14)
C20	0.3787 (3)	0.8422 (8)	−0.5512 (9)	0.0349 (14)
H20	0.3453	0.9050	−0.6294	0.042*
C21	0.4385 (3)	0.8444 (8)	−0.6291 (9)	0.0299 (13)
H21	0.4460	0.9096	−0.7589	0.036*
C22	0.2927 (3)	0.6724 (9)	−0.1012 (10)	0.0426 (16)
H22B	0.3163	0.7297	0.0254	0.051*
H22A	0.3041	0.5412	−0.1060	0.051*
O5	0.2061 (4)	0.6830 (10)	0.1419 (11)	0.061 (2)	0.797 (9)
C23	0.2222 (4)	0.6948 (12)	−0.0834 (13)	0.056 (2)	0.797 (9)
H23	0.1924	0.6448	−0.2014	0.067*	0.797 (9)
C24	0.2043 (5)	0.8605 (11)	0.0384 (15)	0.063 (2)	0.797 (9)
H24B	0.2380	0.9489	0.0829	0.075*	0.797 (9)
H24A	0.1626	0.9157	0.0004	0.075*	0.797 (9)
O5'	0.1776 (12)	0.714 (4)	−0.023 (4)	0.063 (3)	0.203 (9)
C23'	0.2400 (10)	0.788 (4)	−0.012 (6)	0.059 (3)	0.203 (9)
H23A	0.2427	0.9221	−0.0413	0.071*	0.203 (9)
C24'	0.207 (2)	0.737 (8)	0.193 (4)	0.061 (3)	0.203 (9)
H24C	0.2210	0.6258	0.2739	0.073*	0.203 (9)
H24D	0.1915	0.8373	0.2843	0.073*	0.203 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.028 (2)	0.047 (3)	0.042 (3)	0.011 (2)	−0.0011 (18)	−0.008 (2)
O3	0.030 (2)	0.042 (3)	0.028 (2)	−0.0026 (18)	0.0013 (17)	−0.0061 (18)
O4	0.040 (3)	0.042 (3)	0.041 (2)	0.006 (2)	0.001 (2)	0.011 (2)
O1	0.060 (4)	0.069 (5)	0.053 (4)	0.006 (4)	−0.008 (3)	−0.003 (4)
C1	0.057 (4)	0.064 (5)	0.058 (4)	0.004 (4)	−0.005 (4)	−0.005 (4)
C2	0.053 (4)	0.063 (5)	0.048 (4)	0.002 (4)	−0.001 (4)	−0.003 (4)
O1'	0.058 (4)	0.069 (5)	0.052 (5)	0.005 (4)	−0.003 (4)	−0.003 (4)
C1'	0.056 (5)	0.067 (5)	0.052 (5)	0.003 (4)	−0.001 (4)	0.000 (4)
C2'	0.056 (5)	0.064 (5)	0.053 (5)	0.003 (4)	−0.007 (4)	−0.002 (4)
C3	0.039 (4)	0.062 (5)	0.047 (4)	0.015 (3)	−0.012 (3)	−0.011 (4)
C4	0.022 (3)	0.029 (3)	0.032 (3)	0.007 (2)	0.002 (2)	0.005 (2)
C5	0.045 (4)	0.029 (3)	0.032 (3)	−0.003 (3)	0.000 (3)	0.003 (2)
C6	0.045 (4)	0.027 (3)	0.032 (3)	0.009 (3)	0.001 (3)	0.001 (3)
C7	0.031 (3)	0.024 (3)	0.025 (3)	−0.004 (2)	0.005 (2)	0.011 (2)
C8	0.033 (3)	0.032 (3)	0.031 (3)	0.004 (3)	0.007 (3)	−0.006 (2)
C9	0.024 (3)	0.033 (3)	0.035 (3)	0.009 (2)	0.013 (2)	−0.003 (3)
C10	0.031 (3)	0.022 (3)	0.026 (3)	0.003 (2)	0.008 (2)	−0.002 (2)
C11	0.044 (4)	0.026 (3)	0.030 (3)	−0.002 (3)	0.000 (3)	−0.006 (2)
C12	0.037 (4)	0.028 (3)	0.038 (3)	−0.005 (3)	−0.001 (3)	−0.005 (3)
C13	0.036 (3)	0.026 (3)	0.032 (3)	−0.018 (3)	0.004 (3)	0.002 (2)
C14	0.033 (3)	0.035 (3)	0.022 (3)	0.005 (3)	0.002 (2)	−0.006 (2)
C15	0.025 (3)	0.039 (3)	0.032 (3)	−0.003 (3)	0.016 (2)	−0.004 (3)
C16	0.036 (3)	0.020 (3)	0.033 (3)	0.001 (2)	0.003 (2)	−0.011 (2)
C17	0.028 (3)	0.028 (3)	0.031 (3)	0.000 (2)	−0.002 (2)	0.002 (2)
C18	0.045 (4)	0.030 (3)	0.036 (3)	−0.003 (3)	0.001 (3)	−0.004 (3)
C19	0.019 (3)	0.034 (3)	0.040 (3)	0.007 (2)	−0.005 (2)	−0.009 (3)
C20	0.041 (4)	0.033 (3)	0.030 (3)	0.009 (3)	−0.008 (3)	0.007 (3)
C21	0.033 (3)	0.030 (3)	0.027 (3)	0.000 (3)	0.004 (2)	0.007 (2)
C22	0.034 (3)	0.050 (4)	0.044 (4)	0.004 (3)	0.007 (3)	0.017 (3)
O5	0.057 (3)	0.071 (4)	0.058 (3)	0.011 (3)	0.024 (3)	0.009 (3)
C23	0.055 (4)	0.063 (4)	0.053 (4)	0.006 (4)	0.020 (3)	0.001 (4)
C24	0.060 (4)	0.066 (4)	0.064 (4)	0.006 (4)	0.016 (3)	0.002 (4)
O5'	0.061 (5)	0.070 (5)	0.061 (5)	0.005 (5)	0.017 (4)	0.002 (5)
C23'	0.058 (5)	0.064 (5)	0.057 (5)	0.005 (5)	0.015 (5)	0.004 (5)
C24'	0.060 (5)	0.067 (6)	0.058 (5)	0.007 (5)	0.017 (5)	0.002 (5)

Geometric parameters (Å, º) top

O2—C4	1.378 (7)	C11—C12	1.386 (8)
O2—C3	1.437 (7)	C11—H11	0.9500
O3—C16	1.385 (7)	C12—C13	1.393 (8)
O3—C13	1.395 (7)	C12—H12	0.9500
O4—C19	1.374 (7)	C13—C14	1.377 (8)
O4—C22	1.416 (7)	C14—C15	1.385 (8)
O1—C2	1.427 (8)	C14—H14	0.9500
O1—C1	1.466 (9)	C15—H15	0.9500
C1—C2	1.434 (13)	C16—C21	1.382 (8)
C1—H1B	0.9900	C16—C17	1.388 (8)
C1—H1A	0.9900	C17—C18	1.387 (8)
C2—C3	1.517 (8)	C17—H17	0.9500
C2—H2	1.0000	C18—C19	1.405 (8)
O1'—C2'	1.423 (10)	C18—H18	0.9500
O1'—C1'	1.444 (10)	C19—C20	1.359 (9)
C1'—C2'	1.498 (18)	C20—C21	1.386 (8)
C1'—H1'B	0.9900	C20—H20	0.9500
C1'—H1'A	0.9900	C21—H21	0.9500
C2'—C3	1.532 (10)	C22—C23	1.519 (8)
C2'—H2'	1.0000	C22—C23'	1.532 (10)
C3—H3A	0.9900	C22—H22B	0.9900
C3—H3B	0.9900	C22—H22A	0.9900
C4—C5	1.373 (8)	O5—C24	1.444 (8)
C4—C9	1.383 (8)	O5—C23	1.447 (8)
C5—C6	1.387 (8)	C23—C24	1.485 (8)
C5—H5	0.9500	C23—H23	1.0000
C6—C7	1.410 (8)	C24—H24B	0.9900
C6—H6	0.9500	C24—H24A	0.9900
C7—C8	1.404 (8)	O5'—C23'	1.430 (10)
C7—C10	1.476 (7)	O5'—C24'	1.435 (10)
C8—C9	1.369 (8)	C23'—C24'	1.526 (10)
C8—H8	0.9500	C23'—H23A	1.0000
C9—H9	0.9500	C24'—H24C	0.9900
C10—C15	1.383 (8)	C24'—H24D	0.9900
C10—C11	1.398 (8)

C4—O2—C3	117.8 (4)	C13—C12—H12	120.8
C16—O3—C13	120.6 (4)	C14—C13—C12	120.2 (6)
C19—O4—C22	118.8 (5)	C14—C13—O3	115.6 (5)
C2—O1—C1	59.4 (6)	C12—C13—O3	124.0 (6)
C2—C1—O1	59.0 (5)	C13—C14—C15	119.1 (5)
C2—C1—H1B	117.9	C13—C14—H14	120.4
O1—C1—H1B	117.9	C15—C14—H14	120.4
C2—C1—H1A	117.9	C10—C15—C14	123.5 (5)
O1—C1—H1A	117.9	C10—C15—H15	118.3
H1B—C1—H1A	115.0	C14—C15—H15	118.3
O1—C2—C1	61.6 (5)	C21—C16—O3	115.8 (5)
O1—C2—C3	112.2 (9)	C21—C16—C17	120.0 (5)
C1—C2—C3	114.5 (10)	O3—C16—C17	123.9 (5)
O1—C2—H2	118.6	C18—C17—C16	119.9 (5)
C1—C2—H2	118.6	C18—C17—H17	120.0
C3—C2—H2	118.6	C16—C17—H17	120.0
C2'—O1'—C1'	63.0 (9)	C17—C18—C19	119.4 (6)
O1'—C1'—C2'	57.8 (6)	C17—C18—H18	120.3
O1'—C1'—H1'B	118.0	C19—C18—H18	120.3
C2'—C1'—H1'B	118.0	C20—C19—O4	116.6 (5)
O1'—C1'—H1'A	118.0	C20—C19—C18	119.9 (6)
C2'—C1'—H1'A	118.0	O4—C19—C18	123.5 (5)
H1'B—C1'—H1'A	115.2	C19—C20—C21	120.9 (5)
O1'—C2'—C1'	59.2 (6)	C19—C20—H20	119.6
O1'—C2'—C3	118.9 (16)	C21—C20—H20	119.6
C1'—C2'—C3	114.3 (16)	C16—C21—C20	119.8 (5)
O1'—C2'—H2'	117.2	C16—C21—H21	120.1
C1'—C2'—H2'	117.2	C20—C21—H21	120.1
C3—C2'—H2'	117.2	O4—C22—C23	105.8 (5)
O2—C3—C2	104.2 (6)	O4—C22—C23'	104.5 (14)
O2—C3—C2'	105.6 (8)	O4—C22—H22B	110.6
O2—C3—H3A	110.9	C23—C22—H22B	110.6
C2—C3—H3A	110.9	C23'—C22—H22B	80.3
C2'—C3—H3A	75.9	O4—C22—H22A	110.6
O2—C3—H3B	110.9	C23—C22—H22A	110.6
C2—C3—H3B	110.9	C23'—C22—H22A	136.9
C2'—C3—H3B	137.7	H22B—C22—H22A	108.7
H3A—C3—H3B	108.9	C24—O5—C23	61.8 (4)
C5—C4—O2	125.1 (5)	O5—C23—C24	59.0 (4)
C5—C4—C9	119.3 (5)	O5—C23—C22	110.8 (7)
O2—C4—C9	115.6 (5)	C24—C23—C22	114.1 (8)
C4—C5—C6	119.6 (5)	O5—C23—H23	119.5
C4—C5—H5	120.2	C24—C23—H23	119.5
C6—C5—H5	120.2	C22—C23—H23	119.5
C5—C6—C7	122.7 (6)	O5—C24—C23	59.2 (4)
C5—C6—H6	118.7	O5—C24—H24B	117.9
C7—C6—H6	118.7	C23—C24—H24B	117.9
C8—C7—C6	115.4 (6)	O5—C24—H24A	117.9
C8—C7—C10	122.3 (5)	C23—C24—H24A	117.9
C6—C7—C10	122.3 (5)	H24B—C24—H24A	115.0
C9—C8—C7	121.9 (5)	C23'—O5'—C24'	64.3 (6)
C9—C8—H8	119.0	O5'—C23'—C24'	58.0 (6)
C7—C8—H8	119.0	O5'—C23'—C22	118 (2)
C8—C9—C4	121.1 (5)	C24'—C23'—C22	123 (3)
C8—C9—H9	119.4	O5'—C23'—H23A	115.1
C4—C9—H9	119.4	C24'—C23'—H23A	115.1
C15—C10—C11	115.3 (5)	C22—C23'—H23A	115.1
C15—C10—C7	122.1 (5)	O5'—C24'—C23'	57.7 (5)
C11—C10—C7	122.6 (5)	O5'—C24'—H24C	118.0
C12—C11—C10	123.3 (5)	C23'—C24'—H24C	118.0
C12—C11—H11	118.3	O5'—C24'—H24D	118.0
C10—C11—H11	118.3	C23'—C24'—H24D	118.0
C11—C12—C13	118.5 (6)	H24C—C24'—H24D	115.2
C11—C12—H12	120.8

C1—O1—C2—C3	106.7 (11)	C16—O3—C13—C14	154.0 (5)
O1—C1—C2—C3	−103.1 (10)	C16—O3—C13—C12	−31.6 (8)
C1'—O1'—C2'—C3	−103 (2)	C12—C13—C14—C15	1.5 (9)
O1'—C1'—C2'—C3	110.3 (19)	O3—C13—C14—C15	176.2 (5)
C4—O2—C3—C2	−174.2 (6)	C11—C10—C15—C14	−0.9 (8)
C4—O2—C3—C2'	146.9 (9)	C7—C10—C15—C14	179.3 (5)
O1—C2—C3—O2	−161.3 (8)	C13—C14—C15—C10	−0.3 (9)
C1—C2—C3—O2	−93.5 (9)	C13—O3—C16—C21	147.4 (5)
O1—C2—C3—C2'	−64.0 (15)	C13—O3—C16—C17	−38.3 (8)
C1—C2—C3—C2'	3.8 (13)	C21—C16—C17—C18	−0.5 (8)
O1'—C2'—C3—O2	163.7 (14)	O3—C16—C17—C18	−174.6 (5)
C1'—C2'—C3—O2	96.8 (14)	C16—C17—C18—C19	0.1 (8)
O1'—C2'—C3—C2	70.6 (16)	C22—O4—C19—C20	−178.4 (6)
C1'—C2'—C3—C2	3.7 (11)	C22—O4—C19—C18	1.3 (9)
C3—O2—C4—C5	0.8 (9)	C17—C18—C19—C20	0.7 (9)
C3—O2—C4—C9	−176.4 (6)	C17—C18—C19—O4	−178.9 (5)
O2—C4—C5—C6	−177.9 (5)	O4—C19—C20—C21	178.5 (5)
C9—C4—C5—C6	−0.8 (9)	C18—C19—C20—C21	−1.2 (9)
C4—C5—C6—C7	−0.7 (9)	O3—C16—C21—C20	174.6 (5)
C5—C6—C7—C8	1.0 (8)	C17—C16—C21—C20	0.1 (8)
C5—C6—C7—C10	−179.1 (5)	C19—C20—C21—C16	0.8 (9)
C6—C7—C8—C9	0.2 (8)	C19—O4—C22—C23	−175.6 (5)
C10—C7—C8—C9	−179.7 (5)	C19—O4—C22—C23'	149.6 (13)
C7—C8—C9—C4	−1.7 (9)	C24—O5—C23—C22	106.3 (8)
C5—C4—C9—C8	2.0 (9)	O4—C22—C23—O5	−155.6 (6)
O2—C4—C9—C8	179.4 (5)	C23'—C22—C23—O5	−63 (3)
C8—C7—C10—C15	−3.2 (8)	O4—C22—C23—C24	−91.2 (7)
C6—C7—C10—C15	176.9 (6)	C23'—C22—C23—C24	1 (2)
C8—C7—C10—C11	177.1 (6)	C22—C23—C24—O5	−100.7 (8)
C6—C7—C10—C11	−2.8 (8)	C24'—O5'—C23'—C22	113 (4)
C15—C10—C11—C12	1.0 (8)	O4—C22—C23'—O5'	107 (2)
C7—C10—C11—C12	−179.2 (5)	C23—C22—C23'—O5'	10.7 (14)
C10—C11—C12—C13	0.1 (9)	O4—C22—C23'—C24'	176 (2)
C11—C12—C13—C14	−1.4 (9)	C23—C22—C23'—C24'	79 (2)
C11—C12—C13—O3	−175.6 (5)	C22—C23'—C24'—O5'	−105 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₅
M_r	390.42
Crystal system, space group	Monoclinic, Pc
Temperature (K)	173
a, b, c (Å)	21.261 (4), 7.3103 (15), 6.1322 (12)
β (°)	93.59 (3)
V (Å³)	951.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.15 × 0.08

Data collection
Diffractometer	Rigaku Saturn724+ CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.983, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6607, 1965, 1728
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.172, 1.18
No. of reflections	1965
No. of parameters	318
No. of restraints	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support. They thank Dr Lin Wang of ICCAS for the X-ray data collection.

References

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