3,3′-[Biphenyl-4,4′-diylbis(­oxy)]diphthalic acid

Zhao, N.; Li, W.; Chang, Z.; Sun, C.; Fan, H.

doi:10.1107/S1600536811053219

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o211

doi:10.1107/S1600536811053219

Open

access

3,3′-[Biphenyl-4,4′-diylbis(oxy)]diphthalic acid

Ningning Zhao,^a Wenjun Li,^a ^* Zhidong Chang,^a Changyan Sun ^a and Hongxia Fan ^a

^aDepartment of Chemistry and Chemical Engineering, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
^*Correspondence e-mail: wjli@sas.ustb.edu.cn

(Received 21 November 2011; accepted 10 December 2011; online 21 December 2011)

In the title molecule, C₂₈H₁₈O₁₀, the two central benzene rings form a dihedral angle of 31.0 (1)°. In the phthalic acid fragments, the carboxy groups in the meta positions are approximately coplanar with the attached benzene rings, being inclined to their planes at 2.7 (1) and 10.3 (1)°, while the carboxy groups in the ortho positions are twisted from the benzene ring planes by 83.5 (1) and 75.4 (1)°. In the crystal, O—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane. Weak C—H⋯O hydrogen bonds and π–π interactions between the aromatic rings [centroid–centroid distance = 3.7674 (3) Å] further consolidate the crystal packing.

Related literature

For applications of metal-organic frameworks with semi-rigid carboxylic acid ligands, see: Li et al. (2008 ); Chen et al. (2008 ). For background to the synthesis of various semi-rigid multicarboxylate ligands, see: Maglio et al. (1997 ).

Experimental

Crystal data

C₂₈H₁₈O₁₀
M_r = 514.42
Orthorhombic, P n a 2₁
a = 21.5817 (7) Å
b = 11.2676 (4) Å
c = 9.5025 (3) Å
V = 2310.76 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.39 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.957, T_max = 0.969
5587 measured reflections
2857 independent reflections
2352 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.118
S = 1.08
2857 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O7ⁱ	0.82	1.85	2.649 (4)	164
O8—H8A⋯O1ⁱⁱ	0.82	1.85	2.659 (4)	169
O3—H3⋯O6ⁱⁱⁱ	0.82	1.76	2.575 (4)	172
O5—H5⋯O4^iv	0.82	1.92	2.732 (4)	169
C11—H11⋯O6^v	0.93	2.46	3.284 (5)	148
C13—H13⋯O3^vi	0.93	2.51	3.438 (6)	173
C16—H16⋯O6^v	0.93	2.54	3.431 (6)	161
Symmetry codes: (i) x, y+1, z+2; (ii) x, y-1, z-2; (iii) $[-x+1, -y+2, z+{\script{3\over 2}}]$ ; (iv) $[-x+1, -y+2, z-{\script{3\over 2}}]$ ; (v) x, y, z+1; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: 10.1107/S1600536811053219/cv5208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053219/cv5208Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053219/cv5208Isup3.cml

checkCIF report

Comment top

Various semirigid multicarboxylate ligands are being used in design of metal-organic frameworks (MOFs) having various potential applications (Chen et al., 2008; Li et al., 2008). Herewith we report the synthesis (Maglio et al., 1997) and single-crystal structure of the title compound - a new semirigid multicarboxylate ligand containing two semirigid phthalic acid groups.

In the title molecule (Fig.1), two central benzene rings form a dihedral angle of 31.0 (1)°. In the phthalic acid fragments, the carboxy groups in meta positions are approximately coplanar with the attached benzene rings being inclined to their planes at 2.7 (1) and 10.3 (1)°, respectively, while carboxy groups in ortho positions are twisted from the benzene rings at 83.5 (1) and 75.4 (1)°, respectively. In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane. Weak intermolecular C—H···O hydrogen bonds (Table 1) and π–π interactions between the aromatic rings [centroid-centroid distance of 3.7674 (3) Å] consolidate further the crystal packing.

Related literature top

For applications of metal-organic frameworks with semi-rigid carboxylic acid ligands, see: Li et al. (2008); Chen et al. (2008). For background to the synthesis of various semi-rigid multicarboxylate ligands, see: Maglio et al. (1997).

Experimental top

To a solution of 4,4'-biphenol(1.62 g,0.01 mol) and anhydrous Na2CO3(2.12 g,0.02 mol) in DMF(25 ml)stirred for 30 min, 3-nitropthalonitrile(3.46 g,0.02 mol) was added.The resulting mixture was stirred for 48 h. Then the mixture was poured into water (500 ml), and a slightly yellow solid was yielded and isolated by filtration. The crude product was dried in air, yielding 3,3'-(4,4'-biphenylenebis(oxy))diphthalonitrile. The mixture of 3,3'-(4,4'-biphenylenebis(oxy))diphthalonitrile (3.6 g, 0.01 mol) and NaOH (3.2 g, 0.08 mol) in distilled water (150 ml) was refluxed until the solution turned clear Then, the solution was cooled drown to room temperature and filtered. After the pH value of the filtrate was adjusted to about 4–5 with HCl (6.0 mol/L), the filtrate was kept undisturbed at room temperature. After about one day, a large amount of yellow solid of (I) was collected by filtration. A mixture containing Zn(NO₃)₂.6H₂O (0.0595 g, 0.2 mmol), (I)(0.0514 g, 0.1 mmol), and H₂O (15 ml) was sealed in a Teflon-lined stainless steel reactor and heated at 120 for 3 days. Unfortunately, X-ray quality single crystals of (I) were only obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

3,3'-[Biphenyl-4,4'-diylbis(oxy)]diphthalic acid top

Crystal data top

C₂₈H₁₈O₁₀	D_x = 1.479 Mg m⁻³
M_r = 514.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1882 reflections
a = 21.5817 (7) Å	θ = 3.0–29.1°
b = 11.2676 (4) Å	µ = 0.11 mm⁻¹
c = 9.5025 (3) Å	T = 293 K
V = 2310.76 (13) Å³	Block, yellow
Z = 4	0.39 × 0.32 × 0.28 mm
F(000) = 1064

Data collection top

Bruker APEXII CCD area-detector diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→25
T_min = 0.957, T_max = 0.969	k = −13→9
5587 measured reflections	l = −5→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0626P)² + 0.1818P] where P = (F_o² + 2F_c²)/3
2857 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₈H₁₈O₁₀	V = 2310.76 (13) Å³
M_r = 514.42	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 21.5817 (7) Å	µ = 0.11 mm⁻¹
b = 11.2676 (4) Å	T = 293 K
c = 9.5025 (3) Å	0.39 × 0.32 × 0.28 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2857 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2352 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.969	R_int = 0.024
5587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.118	H-atom parameters constrained
S = 1.08	Δρ_max = 0.18 e Å⁻³
2857 reflections	Δρ_min = −0.16 e Å⁻³
343 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
C1	0.30406 (19)	1.3782 (3)	1.6071 (4)	0.0542 (10)
C2	0.41811 (18)	1.3386 (3)	1.4287 (4)	0.0450 (9)
C3	0.30093 (19)	1.3259 (3)	1.4624 (4)	0.0527 (10)
C4	0.35348 (17)	1.3116 (3)	1.3805 (4)	0.0445 (9)
C5	0.34704 (19)	1.2629 (3)	1.2462 (4)	0.0515 (10)
C6	0.2897 (2)	1.2302 (4)	1.1958 (5)	0.0638 (12)
H6	0.2860	1.1980	1.1061	0.077*
C7	0.2378 (2)	1.2454 (4)	1.2786 (5)	0.0691 (13)
H7	0.1990	1.2236	1.2444	0.083*
C8	0.2431 (2)	1.2924 (4)	1.4110 (5)	0.0609 (11)
H8	0.2081	1.3020	1.4667	0.073*
C9	0.40425 (18)	1.1761 (4)	1.0552 (4)	0.0509 (10)
C10	0.3961 (2)	1.0575 (4)	1.0751 (4)	0.0666 (13)
H10	0.3870	1.0279	1.1641	0.080*
C11	0.4016 (2)	0.9812 (3)	0.9611 (5)	0.0609 (12)
H11	0.3963	0.9001	0.9749	0.073*
C12	0.41474 (16)	1.0225 (3)	0.8286 (4)	0.0446 (9)
C13	0.4236 (2)	1.1432 (3)	0.8129 (5)	0.0589 (11)
H13	0.4335	1.1738	0.7248	0.071*
C14	0.4178 (2)	1.2195 (3)	0.9266 (5)	0.0596 (11)
H14	0.4233	1.3007	0.9142	0.071*
C15	0.41748 (16)	0.9389 (3)	0.7056 (4)	0.0438 (9)
C16	0.4346 (2)	0.8221 (3)	0.7200 (4)	0.0616 (11)
H16	0.4469	0.7950	0.8082	0.074*
C17	0.4343 (2)	0.7437 (4)	0.6092 (5)	0.0624 (11)
H17	0.4464	0.6653	0.6227	0.075*
C18	0.41619 (17)	0.7812 (3)	0.4798 (4)	0.0467 (9)
C19	0.3990 (2)	0.8959 (3)	0.4610 (5)	0.0639 (12)
H19	0.3865	0.9217	0.3724	0.077*
C20	0.3997 (2)	0.9744 (3)	0.5721 (4)	0.0606 (12)
H20	0.3881	1.0529	0.5571	0.073*
C21	0.42764 (16)	0.6151 (3)	0.1051 (4)	0.0410 (8)
C22	0.3124 (2)	0.5020 (3)	−0.0191 (4)	0.0539 (10)
C23	0.31384 (17)	0.5530 (3)	0.1252 (4)	0.0458 (9)
C24	0.36704 (17)	0.6045 (3)	0.1821 (4)	0.0421 (8)
C25	0.36412 (17)	0.6571 (3)	0.3145 (4)	0.0466 (9)
C26	0.30915 (18)	0.6577 (4)	0.3882 (4)	0.0587 (11)
H26	0.3074	0.6929	0.4767	0.070*
C27	0.25716 (19)	0.6067 (4)	0.3322 (5)	0.0656 (12)
H27	0.2202	0.6080	0.3824	0.079*
C28	0.2594 (2)	0.5534 (4)	0.2014 (4)	0.0598 (11)
H28	0.2241	0.5177	0.1646	0.072*
O1	0.35545 (15)	1.4066 (3)	1.6566 (3)	0.0855 (10)
O2	0.25406 (16)	1.3930 (3)	1.6720 (3)	0.0896 (11)
H2	0.2612	1.4218	1.7496	0.134*
O3	0.44618 (13)	1.2493 (2)	1.4775 (4)	0.0628 (8)
H3	0.4811	1.2688	1.5023	0.094*
O4	0.43977 (14)	1.4384 (2)	1.4219 (4)	0.0752 (10)
O5	0.46202 (13)	0.5243 (2)	0.0978 (4)	0.0697 (9)
H5	0.4936	0.5406	0.0537	0.105*
O6	0.44146 (14)	0.7116 (2)	0.0561 (4)	0.0679 (9)
O7	0.26478 (17)	0.4490 (3)	−0.0584 (4)	0.0890 (11)
O8	0.35855 (15)	0.5180 (3)	−0.0969 (3)	0.0740 (9)
H8A	0.3525	0.4863	−0.1733	0.111*
O9	0.40081 (14)	1.2559 (3)	1.1684 (3)	0.0626 (8)
O10	0.41860 (12)	0.7034 (2)	0.3652 (3)	0.0551 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (2)	0.072 (2)	0.039 (2)	0.0091 (19)	−0.004 (2)	−0.016 (2)
C2	0.059 (2)	0.0429 (19)	0.0327 (19)	0.0044 (19)	−0.0064 (19)	−0.0080 (16)
C3	0.059 (2)	0.057 (2)	0.042 (2)	0.0023 (18)	−0.004 (2)	−0.014 (2)
C4	0.045 (2)	0.054 (2)	0.035 (2)	−0.0003 (16)	−0.0065 (18)	−0.0138 (17)
C5	0.050 (2)	0.060 (2)	0.044 (2)	−0.0032 (18)	−0.002 (2)	−0.0131 (19)
C6	0.062 (3)	0.082 (3)	0.047 (3)	−0.013 (2)	−0.013 (2)	−0.022 (2)
C7	0.052 (3)	0.098 (3)	0.057 (3)	−0.011 (2)	−0.009 (2)	−0.024 (3)
C8	0.049 (2)	0.083 (3)	0.051 (3)	−0.004 (2)	−0.001 (2)	−0.019 (2)
C9	0.054 (2)	0.060 (2)	0.039 (2)	−0.0010 (19)	−0.003 (2)	−0.016 (2)
C10	0.101 (4)	0.074 (3)	0.025 (2)	0.001 (2)	−0.008 (2)	−0.006 (2)
C11	0.082 (3)	0.054 (2)	0.047 (3)	0.000 (2)	−0.005 (2)	−0.009 (2)
C12	0.0415 (19)	0.0541 (19)	0.038 (2)	0.0004 (16)	−0.0004 (18)	−0.0093 (19)
C13	0.081 (3)	0.061 (2)	0.035 (2)	−0.013 (2)	0.005 (2)	−0.012 (2)
C14	0.076 (3)	0.053 (2)	0.050 (3)	−0.010 (2)	0.005 (2)	−0.012 (2)
C15	0.039 (2)	0.054 (2)	0.038 (2)	−0.0012 (16)	−0.0011 (18)	−0.0119 (18)
C16	0.075 (3)	0.071 (2)	0.038 (2)	0.026 (2)	−0.013 (2)	−0.009 (2)
C17	0.077 (3)	0.057 (2)	0.053 (3)	0.019 (2)	−0.001 (2)	−0.011 (2)
C18	0.044 (2)	0.053 (2)	0.043 (2)	−0.0015 (17)	0.006 (2)	−0.0169 (19)
C19	0.094 (3)	0.066 (2)	0.031 (2)	0.005 (2)	−0.008 (2)	−0.002 (2)
C20	0.089 (3)	0.049 (2)	0.044 (3)	0.003 (2)	−0.002 (2)	−0.0033 (19)
C21	0.047 (2)	0.0430 (19)	0.0329 (19)	0.0040 (16)	0.0014 (17)	−0.0074 (17)
C22	0.057 (3)	0.065 (2)	0.039 (2)	−0.001 (2)	0.010 (2)	−0.009 (2)
C23	0.051 (2)	0.0537 (19)	0.033 (2)	−0.0001 (16)	0.0028 (19)	−0.0076 (17)
C24	0.048 (2)	0.0423 (16)	0.036 (2)	0.0029 (16)	0.0074 (17)	−0.0066 (17)
C25	0.047 (2)	0.0537 (19)	0.039 (2)	−0.0015 (16)	0.0073 (19)	−0.0128 (18)
C26	0.058 (3)	0.083 (3)	0.035 (2)	−0.005 (2)	0.011 (2)	−0.024 (2)
C27	0.049 (2)	0.097 (3)	0.051 (3)	−0.012 (2)	0.016 (2)	−0.024 (2)
C28	0.054 (2)	0.081 (3)	0.045 (2)	−0.009 (2)	0.005 (2)	−0.016 (2)
O1	0.060 (2)	0.141 (3)	0.055 (2)	0.0096 (19)	−0.0108 (16)	−0.046 (2)
O2	0.070 (2)	0.148 (3)	0.0512 (19)	−0.008 (2)	0.0082 (17)	−0.042 (2)
O3	0.0580 (17)	0.0637 (16)	0.067 (2)	−0.0040 (14)	−0.0070 (15)	0.0019 (16)
O4	0.075 (2)	0.0582 (16)	0.092 (3)	−0.0139 (15)	−0.032 (2)	0.0110 (17)
O5	0.0570 (17)	0.0566 (14)	0.096 (3)	0.0102 (13)	0.0271 (18)	0.0128 (17)
O6	0.0712 (19)	0.0516 (15)	0.081 (2)	0.0075 (13)	0.0242 (17)	0.0159 (15)
O7	0.083 (2)	0.132 (3)	0.0516 (18)	−0.042 (2)	0.0072 (18)	−0.037 (2)
O8	0.067 (2)	0.111 (2)	0.0439 (18)	−0.0010 (16)	0.0045 (16)	−0.0348 (17)
O9	0.0624 (18)	0.0821 (18)	0.0433 (17)	−0.0121 (14)	0.0023 (15)	−0.0300 (14)
O10	0.0456 (14)	0.0718 (16)	0.0479 (17)	−0.0056 (12)	0.0097 (13)	−0.0281 (14)

Geometric parameters (Å, º) top

C1—O1	1.246 (5)	C16—C17	1.375 (6)
C1—O2	1.254 (5)	C16—H16	0.9300
C1—C3	1.497 (6)	C17—C18	1.357 (6)
C2—O4	1.219 (4)	C17—H17	0.9300
C2—O3	1.263 (4)	C18—C19	1.357 (5)
C2—C4	1.499 (5)	C18—O10	1.399 (4)
C3—C4	1.385 (5)	C19—C20	1.378 (6)
C3—C8	1.392 (5)	C19—H19	0.9300
C4—C5	1.396 (5)	C20—H20	0.9300
C5—C6	1.377 (6)	C21—O6	1.220 (4)
C5—O9	1.378 (5)	C21—O5	1.266 (4)
C6—C7	1.381 (6)	C21—C24	1.504 (5)
C6—H6	0.9300	C22—O7	1.246 (5)
C7—C8	1.370 (6)	C22—O8	1.253 (5)
C7—H7	0.9300	C22—C23	1.487 (5)
C8—H8	0.9300	C23—C28	1.380 (5)
C9—C14	1.349 (6)	C23—C24	1.395 (5)
C9—C10	1.361 (6)	C24—C25	1.392 (5)
C9—O9	1.404 (4)	C25—O10	1.373 (4)
C10—C11	1.388 (6)	C25—C26	1.378 (5)
C10—H10	0.9300	C26—C27	1.368 (6)
C11—C12	1.372 (6)	C26—H26	0.9300
C11—H11	0.9300	C27—C28	1.381 (6)
C12—C13	1.382 (5)	C27—H27	0.9300
C12—C15	1.503 (5)	C28—H28	0.9300
C13—C14	1.386 (5)	O2—H2	0.8200
C13—H13	0.9300	O3—H3	0.8200
C14—H14	0.9300	O5—H5	0.8200
C15—C16	1.374 (5)	O8—H8A	0.8200
C15—C20	1.384 (6)

O1—C1—O2	123.1 (4)	C15—C16—C17	122.5 (4)
O1—C1—C3	119.2 (4)	C15—C16—H16	118.8
O2—C1—C3	117.7 (4)	C17—C16—H16	118.8
O4—C2—O3	124.7 (4)	C18—C17—C16	119.7 (4)
O4—C2—C4	121.8 (3)	C18—C17—H17	120.1
O3—C2—C4	113.4 (3)	C16—C17—H17	120.1
C4—C3—C8	120.3 (4)	C17—C18—C19	119.6 (4)
C4—C3—C1	121.7 (4)	C17—C18—O10	120.0 (3)
C8—C3—C1	118.0 (4)	C19—C18—O10	120.3 (4)
C3—C4—C5	118.6 (4)	C18—C19—C20	120.5 (4)
C3—C4—C2	124.5 (3)	C18—C19—H19	119.7
C5—C4—C2	116.8 (3)	C20—C19—H19	119.7
C6—C5—O9	123.7 (4)	C19—C20—C15	121.3 (4)
C6—C5—C4	120.8 (4)	C19—C20—H20	119.3
O9—C5—C4	115.4 (3)	C15—C20—H20	119.3
C5—C6—C7	119.9 (4)	O6—C21—O5	123.8 (3)
C5—C6—H6	120.1	O6—C21—C24	118.0 (3)
C7—C6—H6	120.1	O5—C21—C24	118.2 (3)
C8—C7—C6	120.2 (4)	O7—C22—O8	123.2 (4)
C8—C7—H7	119.9	O7—C22—C23	118.6 (4)
C6—C7—H7	119.9	O8—C22—C23	118.2 (4)
C7—C8—C3	120.2 (4)	C28—C23—C24	119.7 (3)
C7—C8—H8	119.9	C28—C23—C22	117.9 (4)
C3—C8—H8	119.9	C24—C23—C22	122.3 (3)
C14—C9—C10	120.6 (4)	C25—C24—C23	119.3 (3)
C14—C9—O9	118.3 (3)	C25—C24—C21	116.4 (3)
C10—C9—O9	121.0 (4)	C23—C24—C21	124.1 (3)
C9—C10—C11	119.3 (4)	O10—C25—C26	123.9 (3)
C9—C10—H10	120.4	O10—C25—C24	116.1 (3)
C11—C10—H10	120.4	C26—C25—C24	120.0 (3)
C12—C11—C10	121.6 (3)	C27—C26—C25	120.4 (4)
C12—C11—H11	119.2	C27—C26—H26	119.8
C10—C11—H11	119.2	C25—C26—H26	119.8
C11—C12—C13	117.5 (3)	C26—C27—C28	120.2 (4)
C11—C12—C15	120.6 (3)	C26—C27—H27	119.9
C13—C12—C15	121.8 (3)	C28—C27—H27	119.9
C12—C13—C14	120.9 (4)	C23—C28—C27	120.3 (4)
C12—C13—H13	119.6	C23—C28—H28	119.9
C14—C13—H13	119.6	C27—C28—H28	119.9
C9—C14—C13	120.1 (3)	C1—O2—H2	109.5
C9—C14—H14	120.0	C2—O3—H3	109.5
C13—C14—H14	120.0	C21—O5—H5	109.5
C16—C15—C20	116.3 (3)	C22—O8—H8A	109.5
C16—C15—C12	122.2 (3)	C5—O9—C9	119.5 (3)
C20—C15—C12	121.4 (3)	C25—O10—C18	118.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O7ⁱ	0.82	1.85	2.649 (4)	164
O8—H8A···O1ⁱⁱ	0.82	1.85	2.659 (4)	169
O3—H3···O6ⁱⁱⁱ	0.82	1.76	2.575 (4)	172
O5—H5···O4^iv	0.82	1.92	2.732 (4)	169
C11—H11···O6^v	0.93	2.46	3.284 (5)	148
C13—H13···O3^vi	0.93	2.51	3.438 (6)	173
C16—H16···O6^v	0.93	2.54	3.431 (6)	161

Symmetry codes: (i) x, y+1, z+2; (ii) x, y−1, z−2; (iii) −x+1, −y+2, z+3/2; (iv) −x+1, −y+2, z−3/2; (v) x, y, z+1; (vi) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₈O₁₀
M_r	514.42
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	21.5817 (7), 11.2676 (4), 9.5025 (3)
V (Å³)	2310.76 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.39 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	5587, 2857, 2352
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.118, 1.08
No. of reflections	2857
No. of parameters	343
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
O2—H2···O7ⁱ	0.82	1.85	2.649 (4)	163.6
O8—H8A···O1ⁱⁱ	0.82	1.85	2.659 (4)	168.5
O3—H3···O6ⁱⁱⁱ	0.82	1.76	2.575 (4)	171.6
O5—H5···O4^iv	0.82	1.92	2.732 (4)	169.0
C11—H11···O6^v	0.93	2.46	3.284 (5)	147.5
C13—H13···O3^vi	0.93	2.51	3.438 (6)	172.5
C16—H16···O6^v	0.93	2.54	3.431 (6)	160.7

Symmetry codes: (i) x, y+1, z+2; (ii) x, y−1, z−2; (iii) −x+1, −y+2, z+3/2; (iv) −x+1, −y+2, z−3/2; (v) x, y, z+1; (vi) x, y, z−1.

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 21101013) and the Foundation of University of Science and Technology Beijing (grant Nos. 00009805 and 06113004).

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X.-L., Zhang, B., Hu, H.-M., Fu, F., Wu, X.-L., Qin, T., Yang, M.-L., Xue, G.-L. & Wang, J.-W. (2008). Cryst. Growth Des. 8, 3706–3712. Web of Science CSD CrossRef CAS Google Scholar
Li, S.-L., Lan, Y.-Q., Ma, J.-F., Yang, J., Wei, G.-H., Zhang, L.-P. & Su, Z.-M. (2008). Cryst. Growth Des. 8, 1610–1616. Web of Science CSD CrossRef CAS Google Scholar
Maglio, G., Palumbo, R., Schioppa, A. & Tesauro, D. (1997). Polymer, 38, 5849–5856. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar