Diethyl 2,5-diphenyl­furan-3,4-dicarboxyl­ate

Hu, S.-L.; Le, Y.-C.; Huang, L.

doi:10.1107/S1600536810045241

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3116

https://doi.org/10.1107/S1600536810045241

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Diethyl 2,5-diphenylfuran-3,4-dicarboxylate

Sheng-Li Hu,^a ^* Yi-Cheng Le ^b and Ling Huang ^a

^aDepartment of Chemistry & Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China, and ^b712th Research Institute, CSIC, Wuhan 430064, People's Republic of China
^*Correspondence e-mail: hushengli168@126.com

(Received 20 October 2010; accepted 4 November 2010; online 10 November 2010)

In the title compound, C₂₂H₂₀O₅, the substituted benzene rings are twisted away from the furan ring, making dihedral angles of 54.91 (14) and 20.96 (15)° with the furan ring. The dihedral angle between the two benzene rings is 46.89 (13)°. One ethyl group of one ethoxycarbonyl unit is disordered over two sets of sites with occupancies of 0.56 (12) and 0.44 (12). In the crystal, weak intramolecular C—H⋯O hydrogen bonds link the molecules into chains along the c axis.

Related literature

For background to the applications of furan-3,4-dicarboxylic acid and its esters, see: Deshpande et al. (2002 ). For related structures, see: Hu & Wu (2005 ) Hu et al. (2005 ). For the synthesis, see: Wu et al. (1997 ).

Experimental

Crystal data

C₂₂H₂₀O₅
M_r = 364.38
Orthorhombic, P b c a
a = 11.9535 (8) Å
b = 17.0116 (12) Å
c = 18.9219 (14) Å
V = 3847.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.965, T_max = 0.993
19957 measured reflections
3778 independent reflections
1952 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.160
S = 1.01
3778 reflections
268 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3	0.93	2.56	3.453 (4)	161

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045241/sj5048sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045241/sj5048Isup2.hkl

checkCIF report

Comment top

Furan-3,4-dicarboxylic acid and its esters have been used as starting materials in the synthesis of several bioactive natural products and several pharmacologically useful molecules, preparation of complexes with rare earth metal ions and also as a potential dienes in Diels-Alder reactions for the synthesis of several novel heterocycles (Deshpande et al., 2002). The crystal structures of some furan-3,4-dicarboxylic acid diethyl esters have been reported previously (Hu & Wu, 2005; Hu et al., 2005). In this paper, we report the crystal structure of the title compound, (I). In compound (I), the C1–C6 and C11–C16 phenyl rings form dihedral angles of 54.91 (14) and 20.96 (15)°, respectively with the furan ring, Fig 1. The dihedral angle between the two benzene rings is 46.89 (13)°. In the crystal structure, weak intramolecular C4—H4···O3 hydrogen bonds link the molecules into chains along the c axis (Table 1 and Fig. 2).

Related literature top

For background to the applications of furan-3,4-dicarboxylic acid and its esters, see: Deshpande et al. (2002). For related structures, see: Hu & Wu (2005) Hu et al. (2005). For the synthesis, see: Wu et al. (1997).

Experimental top

Compound (I) was synthesized according to the literature procedure (Wu et al., 1997). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution at room temperature.

Structure description top

For background to the applications of furan-3,4-dicarboxylic acid and its esters, see: Deshpande et al. (2002). For related structures, see: Hu & Wu (2005) Hu et al. (2005). For the synthesis, see: Wu et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing of (I), viewed along the a axis.

Diethyl 2,5-diphenylfuran-3,4-dicarboxylate top

Crystal data top

C₂₂H₂₀O₅	F(000) = 1536
M_r = 364.38	D_x = 1.258 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1354 reflections
a = 11.9535 (8) Å	θ = 2.3–16.5°
b = 17.0116 (12) Å	µ = 0.09 mm⁻¹
c = 18.9219 (14) Å	T = 293 K
V = 3847.7 (5) Å³	Block, colorless
Z = 8	0.40 × 0.10 × 0.08 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3778 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
T_min = 0.965, T_max = 0.993	k = −18→20
19957 measured reflections	l = −23→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0624P)² + 0.4808P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3778 reflections	Δρ_max = 0.25 e Å⁻³
268 parameters	Δρ_min = −0.27 e Å⁻³
6 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0010 (4)

Crystal data top

C₂₂H₂₀O₅	V = 3847.7 (5) Å³
M_r = 364.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.9535 (8) Å	µ = 0.09 mm⁻¹
b = 17.0116 (12) Å	T = 293 K
c = 18.9219 (14) Å	0.40 × 0.10 × 0.08 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3778 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1952 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.993	R_int = 0.081
19957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	6 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
3778 reflections	Δρ_min = −0.27 e Å⁻³
268 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)
C1	0.8016 (2)	0.14397 (15)	0.62303 (14)	0.0490 (7)
C2	0.8864 (3)	0.17700 (17)	0.58313 (15)	0.0605 (8)
H2	0.9579	0.1817	0.6021	0.073*
C3	0.8659 (4)	0.2028 (2)	0.51602 (17)	0.0791 (10)
H3	0.9234	0.2252	0.4898	0.095*
C4	0.7618 (4)	0.1959 (2)	0.48719 (18)	0.0840 (11)
H4	0.7483	0.2141	0.4417	0.101*
C5	0.6774 (3)	0.1621 (2)	0.52514 (18)	0.0820 (11)
H5	0.6067	0.1569	0.5051	0.098*
C6	0.6963 (3)	0.13579 (18)	0.59302 (16)	0.0665 (9)
H6	0.6387	0.1126	0.6186	0.080*
C7	0.8238 (2)	0.11805 (15)	0.69580 (14)	0.0492 (7)
C8	0.7797 (2)	0.13356 (15)	0.76053 (14)	0.0482 (7)
C9	0.8438 (2)	0.08957 (16)	0.81084 (14)	0.0502 (7)
C10	0.9221 (2)	0.04934 (16)	0.77404 (14)	0.0523 (7)
C11	1.0088 (2)	−0.00776 (16)	0.79305 (15)	0.0527 (7)
C12	1.0976 (3)	−0.02123 (18)	0.74782 (17)	0.0644 (8)
H12	1.1025	0.0058	0.7052	0.077*
C13	1.1795 (3)	−0.0752 (2)	0.7664 (2)	0.0765 (10)
H13	1.2394	−0.0841	0.7361	0.092*
C14	1.1728 (3)	−0.1154 (2)	0.8287 (2)	0.0823 (11)
H14	1.2277	−0.1519	0.8404	0.099*
C15	1.0860 (3)	−0.10230 (19)	0.87366 (19)	0.0791 (10)
H15	1.0820	−0.1295	0.9162	0.095*
C16	1.0039 (3)	−0.04870 (17)	0.85632 (16)	0.0664 (9)
H16	0.9449	−0.0399	0.8873	0.080*
C17	0.6899 (2)	0.18876 (18)	0.77946 (16)	0.0570 (8)
C18	0.5443 (3)	0.27088 (19)	0.73529 (17)	0.0713 (9)
H18A	0.5707	0.3181	0.7587	0.086*
H18B	0.4872	0.2468	0.7645	0.086*
C19	0.4984 (3)	0.2902 (2)	0.66417 (18)	0.0901 (11)
H19A	0.5539	0.3179	0.6372	0.135*
H19B	0.4332	0.3227	0.6694	0.135*
H19C	0.4785	0.2426	0.6401	0.135*
C20	0.8287 (3)	0.08891 (18)	0.88887 (16)	0.0598 (8)
O1	0.91184 (16)	0.06707 (10)	0.70331 (9)	0.0542 (5)
O2	0.63606 (18)	0.21673 (12)	0.72406 (10)	0.0703 (6)
O3	0.66800 (19)	0.20603 (17)	0.83882 (12)	0.1034 (9)
O4	0.7383 (2)	0.04851 (17)	0.90669 (11)	0.1010 (9)
O5	0.89136 (19)	0.11776 (13)	0.93023 (11)	0.0773 (7)
C22	0.6437 (8)	0.0896 (6)	1.0062 (4)	0.108 (3)	0.56
H22A	0.6858	0.1376	1.0073	0.163*	0.56
H22B	0.6179	0.0774	1.0530	0.163*	0.56
H22C	0.5806	0.0956	0.9753	0.163*	0.56
C21	0.7149 (11)	0.0258 (6)	0.9805 (5)	0.088 (4)	0.56
H21A	0.6762	−0.0243	0.9826	0.106*	0.56
H21B	0.7834	0.0223	1.0078	0.106*	0.56
C21'	0.7110 (15)	0.0659 (11)	0.9813 (5)	0.107 (6)	0.44
H21C	0.7015	0.1220	0.9882	0.128*	0.44
H21D	0.7700	0.0475	1.0123	0.128*	0.44
C22'	0.6045 (8)	0.0235 (7)	0.9961 (5)	0.116 (4)	0.44
H22D	0.5445	0.0479	0.9705	0.173*	0.44
H22E	0.5888	0.0255	1.0458	0.173*	0.44
H22F	0.6115	−0.0304	0.9815	0.173*	0.44

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0605 (18)	0.0467 (16)	0.0398 (16)	0.0013 (14)	0.0019 (14)	−0.0015 (13)
C2	0.072 (2)	0.0598 (19)	0.0498 (19)	−0.0033 (16)	0.0079 (16)	0.0032 (15)
C3	0.106 (3)	0.078 (2)	0.053 (2)	−0.002 (2)	0.013 (2)	0.0133 (17)
C4	0.124 (3)	0.081 (3)	0.047 (2)	0.024 (2)	−0.003 (2)	0.0108 (18)
C5	0.088 (3)	0.105 (3)	0.053 (2)	0.015 (2)	−0.012 (2)	−0.006 (2)
C6	0.068 (2)	0.083 (2)	0.0479 (19)	−0.0009 (17)	0.0025 (16)	−0.0035 (17)
C7	0.0581 (18)	0.0435 (16)	0.0458 (18)	−0.0024 (14)	−0.0003 (14)	0.0012 (13)
C8	0.0561 (18)	0.0496 (17)	0.0389 (16)	−0.0037 (14)	0.0023 (14)	0.0003 (13)
C9	0.0573 (17)	0.0552 (17)	0.0380 (16)	−0.0107 (15)	−0.0010 (14)	0.0001 (13)
C10	0.0598 (19)	0.0561 (19)	0.0411 (17)	−0.0076 (16)	−0.0020 (15)	0.0014 (14)
C11	0.0583 (19)	0.0511 (17)	0.0486 (18)	−0.0080 (15)	−0.0070 (15)	−0.0027 (14)
C12	0.065 (2)	0.059 (2)	0.069 (2)	−0.0058 (17)	−0.0023 (18)	0.0043 (16)
C13	0.063 (2)	0.073 (2)	0.093 (3)	−0.0019 (19)	−0.0025 (19)	−0.004 (2)
C14	0.077 (3)	0.070 (2)	0.100 (3)	0.0083 (19)	−0.024 (2)	0.002 (2)
C15	0.093 (3)	0.075 (2)	0.069 (2)	0.011 (2)	−0.018 (2)	0.0121 (18)
C16	0.078 (2)	0.064 (2)	0.057 (2)	0.0032 (18)	−0.0064 (17)	0.0031 (16)
C17	0.062 (2)	0.070 (2)	0.0397 (18)	−0.0095 (16)	−0.0018 (15)	−0.0039 (15)
C18	0.068 (2)	0.074 (2)	0.072 (2)	0.0157 (18)	0.0038 (18)	−0.0095 (17)
C19	0.099 (3)	0.096 (3)	0.075 (3)	0.025 (2)	−0.011 (2)	0.002 (2)
C20	0.064 (2)	0.070 (2)	0.0456 (19)	−0.0010 (17)	−0.0030 (17)	0.0004 (15)
O1	0.0654 (13)	0.0538 (12)	0.0434 (12)	0.0046 (10)	0.0026 (9)	0.0025 (9)
O2	0.0822 (15)	0.0820 (15)	0.0465 (13)	0.0269 (12)	0.0012 (11)	−0.0039 (11)
O3	0.0985 (18)	0.164 (3)	0.0481 (15)	0.0494 (17)	−0.0063 (13)	−0.0242 (15)
O4	0.0833 (17)	0.174 (3)	0.0456 (14)	−0.0452 (18)	0.0023 (12)	0.0138 (15)
O5	0.0858 (16)	0.0948 (17)	0.0513 (14)	−0.0113 (13)	−0.0116 (12)	−0.0124 (12)
C22	0.122 (8)	0.127 (8)	0.076 (6)	0.025 (6)	0.022 (5)	0.004 (5)
C21	0.081 (7)	0.103 (9)	0.081 (7)	−0.008 (5)	0.003 (5)	0.018 (5)
C21'	0.121 (12)	0.162 (17)	0.036 (6)	−0.034 (12)	0.029 (6)	−0.015 (8)
C22'	0.119 (9)	0.105 (9)	0.123 (9)	−0.006 (7)	0.049 (7)	0.033 (7)

Geometric parameters (Å, º) top

C1—C2	1.384 (4)	C15—C16	1.379 (4)
C1—C6	1.387 (4)	C15—H15	0.9300
C1—C7	1.470 (4)	C16—H16	0.9300
C2—C3	1.366 (4)	C17—O3	1.190 (3)
C2—H2	0.9300	C17—O2	1.319 (3)
C3—C4	1.364 (5)	C18—O2	1.448 (3)
C3—H3	0.9300	C18—C19	1.491 (4)
C4—C5	1.365 (5)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.379 (4)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.359 (3)	C20—O5	1.189 (3)
C7—O1	1.371 (3)	C20—O4	1.324 (4)
C8—C9	1.433 (4)	O4—C21	1.475 (8)
C8—C17	1.470 (4)	O4—C21'	1.479 (8)
C9—C10	1.353 (4)	C22—C21	1.462 (9)
C9—C20	1.487 (4)	C22—H22A	0.9600
C10—O1	1.378 (3)	C22—H22B	0.9600
C10—C11	1.465 (4)	C22—H22C	0.9600
C11—C12	1.383 (4)	C21—H21A	0.9700
C11—C16	1.386 (4)	C21—H21B	0.9700
C12—C13	1.387 (4)	C21'—C22'	1.490 (10)
C12—H12	0.9300	C21'—H21C	0.9700
C13—C14	1.365 (5)	C21'—H21D	0.9700
C13—H13	0.9300	C22'—H22D	0.9600
C14—C15	1.360 (5)	C22'—H22E	0.9600
C14—H14	0.9300	C22'—H22F	0.9600

C2—C1—C6	118.8 (3)	C15—C16—C11	120.5 (3)
C2—C1—C7	120.0 (3)	C15—C16—H16	119.7
C6—C1—C7	121.2 (3)	C11—C16—H16	119.7
C3—C2—C1	120.4 (3)	O3—C17—O2	123.6 (3)
C3—C2—H2	119.8	O3—C17—C8	123.2 (3)
C1—C2—H2	119.8	O2—C17—C8	113.1 (2)
C4—C3—C2	120.5 (3)	O2—C18—C19	106.7 (3)
C4—C3—H3	119.7	O2—C18—H18A	110.4
C2—C3—H3	119.7	C19—C18—H18A	110.4
C3—C4—C5	120.0 (3)	O2—C18—H18B	110.4
C3—C4—H4	120.0	C19—C18—H18B	110.4
C5—C4—H4	120.0	H18A—C18—H18B	108.6
C4—C5—C6	120.4 (3)	C18—C19—H19A	109.5
C4—C5—H5	119.8	C18—C19—H19B	109.5
C6—C5—H5	119.8	H19A—C19—H19B	109.5
C5—C6—C1	119.8 (3)	C18—C19—H19C	109.5
C5—C6—H6	120.1	H19A—C19—H19C	109.5
C1—C6—H6	120.1	H19B—C19—H19C	109.5
C8—C7—O1	109.1 (2)	O5—C20—O4	124.1 (3)
C8—C7—C1	135.7 (3)	O5—C20—C9	125.0 (3)
O1—C7—C1	115.2 (2)	O4—C20—C9	110.8 (3)
C7—C8—C9	106.8 (2)	C7—O1—C10	107.9 (2)
C7—C8—C17	128.8 (3)	C17—O2—C18	118.8 (2)
C9—C8—C17	124.2 (2)	C20—O4—C21	122.1 (6)
C10—C9—C8	107.0 (2)	C20—O4—C21'	108.6 (5)
C10—C9—C20	126.2 (3)	C21—O4—C21'	26.8 (8)
C8—C9—C20	126.8 (3)	C22—C21—O4	103.4 (7)
C9—C10—O1	109.1 (2)	C22—C21—H21A	111.1
C9—C10—C11	134.3 (3)	O4—C21—H21A	111.1
O1—C10—C11	116.5 (2)	C22—C21—H21B	111.1
C12—C11—C16	118.9 (3)	O4—C21—H21B	111.1
C12—C11—C10	120.1 (3)	H21A—C21—H21B	109.1
C16—C11—C10	121.0 (3)	O4—C21'—C22'	105.7 (8)
C11—C12—C13	119.7 (3)	O4—C21'—H21C	110.6
C11—C12—H12	120.2	C22'—C21'—H21C	110.6
C13—C12—H12	120.2	O4—C21'—H21D	110.6
C14—C13—C12	120.6 (3)	C22'—C21'—H21D	110.6
C14—C13—H13	119.7	H21C—C21'—H21D	108.7
C12—C13—H13	119.7	C21'—C22'—H22D	109.5
C15—C14—C13	120.2 (3)	C21'—C22'—H22E	109.5
C15—C14—H14	119.9	H22D—C22'—H22E	109.5
C13—C14—H14	119.9	C21'—C22'—H22F	109.5
C14—C15—C16	120.1 (3)	H22D—C22'—H22F	109.5
C14—C15—H15	119.9	H22E—C22'—H22F	109.5
C16—C15—H15	119.9

C6—C1—C2—C3	1.6 (4)	C11—C12—C13—C14	0.3 (5)
C7—C1—C2—C3	−178.6 (3)	C12—C13—C14—C15	−0.6 (5)
C1—C2—C3—C4	−0.4 (5)	C13—C14—C15—C16	0.5 (5)
C2—C3—C4—C5	−0.8 (5)	C14—C15—C16—C11	0.0 (5)
C3—C4—C5—C6	0.8 (5)	C12—C11—C16—C15	−0.4 (4)
C4—C5—C6—C1	0.4 (5)	C10—C11—C16—C15	180.0 (3)
C2—C1—C6—C5	−1.5 (4)	C7—C8—C17—O3	−169.1 (3)
C7—C1—C6—C5	178.7 (3)	C9—C8—C17—O3	5.6 (5)
C2—C1—C7—C8	124.2 (4)	C7—C8—C17—O2	11.2 (4)
C6—C1—C7—C8	−56.0 (5)	C9—C8—C17—O2	−174.0 (2)
C2—C1—C7—O1	−53.9 (3)	C10—C9—C20—O5	69.8 (4)
C6—C1—C7—O1	125.9 (3)	C8—C9—C20—O5	−109.1 (4)
O1—C7—C8—C9	−0.1 (3)	C10—C9—C20—O4	−107.2 (3)
C1—C7—C8—C9	−178.2 (3)	C8—C9—C20—O4	73.8 (4)
O1—C7—C8—C17	175.3 (2)	C8—C7—O1—C10	0.9 (3)
C1—C7—C8—C17	−2.8 (5)	C1—C7—O1—C10	179.4 (2)
C7—C8—C9—C10	−0.6 (3)	C9—C10—O1—C7	−1.3 (3)
C17—C8—C9—C10	−176.3 (2)	C11—C10—O1—C7	177.2 (2)
C7—C8—C9—C20	178.5 (3)	O3—C17—O2—C18	−0.6 (5)
C17—C8—C9—C20	2.8 (4)	C8—C17—O2—C18	179.0 (2)
C8—C9—C10—O1	1.2 (3)	C19—C18—O2—C17	−178.4 (3)
C20—C9—C10—O1	−178.0 (3)	O5—C20—O4—C21	−8.8 (6)
C8—C9—C10—C11	−176.9 (3)	C9—C20—O4—C21	168.3 (5)
C20—C9—C10—C11	4.0 (5)	O5—C20—O4—C21'	17.0 (11)
C9—C10—C11—C12	−160.6 (3)	C9—C20—O4—C21'	−166.0 (10)
O1—C10—C11—C12	21.5 (4)	C20—O4—C21—C22	93.6 (10)
C9—C10—C11—C16	19.1 (5)	C21'—O4—C21—C22	27.6 (18)
O1—C10—C11—C16	−158.9 (3)	C20—O4—C21'—C22'	175.9 (12)
C16—C11—C12—C13	0.2 (4)	C21—O4—C21'—C22'	−58.8 (17)
C10—C11—C12—C13	179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3	0.93	2.56	3.453 (4)	161

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀O₅
M_r	364.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	11.9535 (8), 17.0116 (12), 18.9219 (14)
V (Å³)	3847.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.965, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	19957, 3778, 1952
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.160, 1.01
No. of reflections	3778
No. of parameters	268
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3	0.93	2.56	3.453 (4)	161

Acknowledgements

We are grateful to Hubei Normal University for financial support.

References

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