4,4′-[(5-Carb­oxy-1,3-phenyl­ene)bis­(­oxy)]dibenzoic acid

Du, C.; Wu, W.; Tian, G.

doi:10.1107/S1600536812012275

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1243

doi:10.1107/S1600536812012275

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4,4′-[(5-Carboxy-1,3-phenylene)bis(oxy)]dibenzoic acid

Chao Du,^a Wei Wu ^b and Ge Tian ^c ^*

^aSecond Department of Neurosurgery, Bethune Third Hospital (China–Japan Union Hospital), Jilin University, People's Republic of China, ^bRadiological Department, Tumor Hospital of Jilin Province, People's Republic of China, and ^cState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: tiange@mail.jlu.edu.cn

(Received 2 March 2012; accepted 21 March 2012; online 31 March 2012)

In the title compound, C₂₁H₁₄O₈, the central benzene ring makes dihedral angles of 77.8 (6) and 75.9 (5)° with the outer benzene rings. In the crystal, molecules are linked by O—H⋯O hydrogen bonds involving carboxyl groups, forming one-dimensional ladders. Two-dimensional layers are formed by interpenetration of these one-dimensional ladders.

Related literature

For general background, see: Moulton & Zaworotko,(2001 ); Kitagawa et al.,(2001 ); Lee et al.,(2009 ); Robin & Fromm, (2006 ). For the preparation of title compound, see: Neogi et al.(2009 ). For related structares, see: Lama et al.(2010 ); Pan et al. (2007 ).

Experimental

Crystal data

C₂₁H₁₄O₈
M_r = 394.32
Monoclinic, C 2/c
a = 17.235 (3) Å
b = 13.419 (3) Å
c = 15.586 (3) Å
β = 96.24 (3)°
V = 3583.3 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.33 × 0.29 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.316, T_max = 0.622
16922 measured reflections
4073 independent reflections
2862 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.09
4073 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H6⋯O4ⁱ	0.82	1.87	2.6919 (16)	176.4
O6—H3⋯O8ⁱⁱ	0.82	1.85	2.6615 (18)	169.9
O7—H8⋯O5ⁱⁱⁱ	0.82	1.82	2.6307 (18)	167.2
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXP97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012275/bq2343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012275/bq2343Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012275/bq2343Isup3.cml

checkCIF report

Comment top

As a new kind of functional molecular materials, metal-organic frameworks have received extensive attention for their potential applications in gas storage, catalysis, optoelectronics, sensors, magnetism, luminescence, porous materials and so on. (Moulton & Zaworotko, 2001; Kitagawa et al., 2001; Lee et al., 2009). Organic molecules with O– and N-donors can be used as organic linkers in these coordination polymers (Robin & Fromm, 2006). In fact, there are many organic ligands which are linked by ether bond (Lama et al. 2010; Pan et al., 2007). Here, we report the crystal structure of the title compound.

In the crystal structure, two benzene rings, β(composed of C₈—C₁₃) and γ (composed of C₁₅—C₂₀) are connected to the center ring (α, composed of C₁—C₆) by ether bond. The dihedral angle between α and β is 77.8 (6)°, and between α and γ is 75.9 (5)° (Fig. 1). Strong intermolecular O—H···O hydrogen bonds are formed between the carboxylic acid groups of neighboring molecules (Table 1), which link the molecules to one-dimensional supra-molecular ladder (Fig. 2). The interpenetration among the one-dimensional molecular ladders which are parallel produce two-dimensional layer (Fig. 3).

Related literature top

For general background, see: Moulton & Zaworotko,(2001); Kitagawa et al.,(2001); Lee et al.,(2009); Robin & Fromm, (2006). For the preparation of title compound, see: Neogi et al.(2009). For related structares, see: Lama et al.(2010); Pan et al. (2007).

Experimental top

The title compound was synthesized by a modified literature method (Neogi et al.2009). Methyl 3,5-dihydroxylbenzoate (1.68 g,10 mmol) was dissolved in DMF (50 ml). To this solution was added K₂CO₃ (7 g,51 mmol) and 4-fluorobenzonitrile (2.4 g,20 mmol). The mixture was heated under reflux for 2 days. The resulting solution was poured in 250 ml ice-cold water and kept over-night. The yellow compound was filtered and washed several times with water. The yellow compound (3.73 g, 10 mmol) was allowed to reflux with 6 N NaOH solution (50 ml) for 12 h, cooled to room temperature and acidified with HCl (6 N). Colorless crystalline product was obtained and isolated by filtration, washed with water and dried in vacuum. Zn(NO₃)₂ (0.075 g,0.25 mmol), 4,4'-(5-carboxy-1,3-phenylene)bis(oxy)dibenzoic acid (0.098 g,0.25 mmol), were mixed in water (5 ml). The mixture were placed in a 25 ml Teflon-lined stainless steel autoclave and heated autogenously under pressure for 2 d at 393 K. After cooling to room temperature, the block-shaped colourless crystals were obtained.

Structure description top

For general background, see: Moulton & Zaworotko,(2001); Kitagawa et al.,(2001); Lee et al.,(2009); Robin & Fromm, (2006). For the preparation of title compound, see: Neogi et al.(2009). For related structares, see: Lama et al.(2010); Pan et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXP97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme, with 50% probability displacement ellipsoids.
	Fig. 2. The packing of title compound, showing one ladder of molecules connected by O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. The interpenetration among the one-dimensional ladders, showing two-dimensional layer. H atoms not involved in hydrogen bonding have been omitted for clarity.

4,4'-[(5-Carboxy-1,3-phenylene)bis(oxy)]dibenzoic acid top

Crystal data top

C₂₁H₁₄O₈	F(000) = 1632
M_r = 394.32	D_x = 1.462 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4073 reflections
a = 17.235 (3) Å	θ = 3.0–27.5°
b = 13.419 (3) Å	µ = 0.11 mm⁻¹
c = 15.586 (3) Å	T = 293 K
β = 96.24 (3)°	Block, colourless
V = 3583.3 (12) Å³	0.33 × 0.29 × 0.25 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4073 independent reflections
Radiation source: fine-focus sealed tube	2862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
phi and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −22→22
T_min = 0.316, T_max = 0.622	k = −17→17
16922 measured reflections	l = −19→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0601P)² + 0.3436P] where P = (F_o² + 2F_c²)/3
4073 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₄O₈	V = 3583.3 (12) Å³
M_r = 394.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.235 (3) Å	µ = 0.11 mm⁻¹
b = 13.419 (3) Å	T = 293 K
c = 15.586 (3) Å	0.33 × 0.29 × 0.25 mm
β = 96.24 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4073 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2862 reflections with I > 2σ(I)
T_min = 0.316, T_max = 0.622	R_int = 0.046
16922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
4073 reflections	Δρ_min = −0.22 e Å⁻³
262 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
O1	0.16748 (7)	0.89288 (12)	−0.11510 (7)	0.0630 (4)
O2	−0.07879 (6)	0.73896 (9)	−0.14922 (7)	0.0404 (3)
O3	−0.06065 (6)	0.88133 (11)	0.15033 (7)	0.0503 (4)
H6	−0.0624	0.8964	0.2011	0.080*
O4	0.06498 (6)	0.92236 (9)	0.18120 (7)	0.0386 (3)
O5	0.44526 (7)	1.12170 (10)	0.10342 (8)	0.0533 (3)
O6	0.48890 (7)	0.96517 (11)	0.10924 (10)	0.0622 (4)
H3	0.5260	0.9916	0.1379	0.080*
O7	−0.42509 (6)	0.81151 (10)	−0.31119 (8)	0.0517 (3)
H8	−0.4653	0.8389	−0.3320	0.080*
O8	−0.38899 (7)	0.96958 (10)	−0.28672 (8)	0.0510 (3)
C1	0.10101 (8)	0.87058 (14)	−0.07678 (10)	0.0383 (4)
C2	0.04339 (9)	0.82152 (13)	−0.12950 (10)	0.0389 (4)
H11A	0.0509	0.8057	−0.1861	0.080*
C3	−0.02518 (8)	0.79647 (12)	−0.09712 (10)	0.0335 (4)
C4	−0.03815 (8)	0.82052 (12)	−0.01343 (10)	0.0338 (4)
H9A	−0.0852	0.8047	0.0074	0.080*
C5	0.02053 (8)	0.86866 (12)	0.03845 (9)	0.0305 (3)
C6	0.09117 (8)	0.89385 (12)	0.00791 (9)	0.0340 (4)
H13A	0.1305	0.9254	0.0435	0.080*
C7	0.01100 (8)	0.89365 (12)	0.13006 (10)	0.0318 (3)
C8	0.23310 (9)	0.92824 (16)	−0.06384 (10)	0.0457 (5)
C9	0.24061 (9)	1.02836 (17)	−0.04567 (12)	0.0520 (5)
H3A	0.2011	1.0727	−0.0652	0.080*
C10	0.30817 (10)	1.06221 (15)	0.00240 (12)	0.0475 (4)
H2A	0.3139	1.1296	0.0154	0.080*
C11	0.36696 (8)	0.99590 (14)	0.03100 (10)	0.0379 (4)
C12	0.35866 (10)	0.89573 (15)	0.01005 (12)	0.0491 (5)
H6A	0.3984	0.8512	0.0282	0.080*
C13	0.29151 (10)	0.86173 (16)	−0.03783 (11)	0.0510 (5)
H5A	0.2860	0.7946	−0.0522	0.080*
C14	0.43795 (9)	1.03153 (14)	0.08419 (11)	0.0393 (4)
C15	−0.15218 (8)	0.77687 (12)	−0.17470 (9)	0.0310 (3)
C16	−0.20659 (9)	0.70800 (13)	−0.21092 (11)	0.0396 (4)
H17A	−0.1938	0.6408	−0.2131	0.080*
C17	−0.27973 (9)	0.74089 (13)	−0.24351 (11)	0.0407 (4)
H16A	−0.3166	0.6952	−0.2673	0.080*
C18	−0.29914 (8)	0.84138 (13)	−0.24126 (10)	0.0340 (4)
C19	−0.24389 (9)	0.90878 (13)	−0.20428 (10)	0.0380 (4)
H20A	−0.2565	0.9761	−0.2023	0.080*
C20	−0.17048 (9)	0.87698 (13)	−0.17049 (10)	0.0367 (4)
H19A	−0.1340	0.9223	−0.1453	0.080*
C21	−0.37538 (9)	0.87785 (13)	−0.28147 (10)	0.0376 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0313 (6)	0.1242 (13)	0.0339 (6)	−0.0307 (7)	0.0050 (5)	−0.0151 (7)
O2	0.0226 (5)	0.0450 (7)	0.0501 (7)	0.0008 (5)	−0.0117 (5)	−0.0106 (5)
O3	0.0275 (6)	0.0879 (10)	0.0359 (6)	−0.0055 (6)	0.0051 (5)	−0.0026 (6)
O4	0.0332 (6)	0.0474 (7)	0.0347 (6)	−0.0087 (5)	0.0009 (5)	−0.0024 (5)
O5	0.0394 (7)	0.0487 (9)	0.0676 (9)	−0.0075 (6)	−0.0131 (6)	−0.0023 (6)
O6	0.0382 (7)	0.0610 (10)	0.0805 (9)	0.0024 (7)	−0.0247 (6)	−0.0065 (7)
O7	0.0291 (6)	0.0479 (8)	0.0730 (9)	0.0008 (5)	−0.0179 (6)	−0.0011 (6)
O8	0.0401 (7)	0.0423 (8)	0.0657 (8)	0.0062 (6)	−0.0167 (6)	−0.0016 (6)
C1	0.0226 (7)	0.0587 (12)	0.0329 (8)	−0.0054 (7)	0.0002 (6)	0.0002 (8)
C2	0.0266 (8)	0.0567 (12)	0.0317 (8)	−0.0007 (7)	−0.0045 (6)	−0.0038 (7)
C3	0.0207 (7)	0.0385 (9)	0.0386 (8)	0.0009 (6)	−0.0088 (6)	−0.0009 (7)
C4	0.0215 (7)	0.0412 (10)	0.0378 (8)	−0.0012 (6)	−0.0016 (6)	0.0027 (7)
C5	0.0242 (7)	0.0348 (9)	0.0316 (7)	0.0010 (6)	−0.0014 (6)	0.0048 (6)
C6	0.0242 (7)	0.0442 (10)	0.0320 (8)	−0.0050 (7)	−0.0036 (6)	0.0010 (7)
C7	0.0254 (7)	0.0353 (9)	0.0340 (8)	0.0012 (6)	0.0000 (6)	0.0043 (6)
C8	0.0257 (8)	0.0812 (15)	0.0303 (8)	−0.0177 (9)	0.0038 (7)	−0.0046 (9)
C9	0.0272 (8)	0.0777 (15)	0.0488 (10)	0.0032 (9)	−0.0062 (7)	0.0007 (10)
C10	0.0311 (9)	0.0559 (12)	0.0537 (11)	−0.0020 (8)	−0.0039 (8)	−0.0007 (9)
C11	0.0259 (8)	0.0483 (11)	0.0383 (8)	−0.0064 (7)	−0.0018 (6)	0.0044 (8)
C12	0.0402 (9)	0.0508 (12)	0.0537 (11)	−0.0071 (8)	−0.0072 (8)	0.0019 (9)
C13	0.0452 (10)	0.0584 (13)	0.0481 (10)	−0.0179 (9)	−0.0011 (9)	−0.0028 (9)
C14	0.0264 (8)	0.0454 (11)	0.0444 (9)	−0.0010 (7)	−0.0031 (7)	0.0028 (8)
C15	0.0211 (7)	0.0401 (9)	0.0307 (7)	−0.0023 (6)	−0.0026 (6)	0.0010 (7)
C16	0.0287 (8)	0.0352 (10)	0.0518 (10)	−0.0024 (7)	−0.0098 (7)	−0.0023 (7)
C17	0.0260 (8)	0.0401 (10)	0.0526 (10)	−0.0063 (7)	−0.0106 (7)	−0.0001 (8)
C18	0.0246 (7)	0.0408 (10)	0.0353 (8)	−0.0009 (7)	−0.0033 (6)	0.0021 (7)
C19	0.0325 (8)	0.0379 (10)	0.0412 (9)	0.0015 (7)	−0.0065 (7)	0.0004 (7)
C20	0.0289 (8)	0.0396 (10)	0.0394 (8)	−0.0070 (7)	−0.0065 (7)	−0.0021 (7)
C21	0.0265 (8)	0.0438 (11)	0.0406 (9)	−0.0007 (7)	−0.0043 (7)	−0.0004 (7)

Geometric parameters (Å, º) top

O1—C1	1.3811 (18)	C8—C13	1.373 (3)
O1—C8	1.395 (2)	C8—C9	1.376 (3)
O2—C15	1.3810 (17)	C9—C10	1.391 (2)
O2—C3	1.3949 (18)	C9—H3A	0.9300
O3—C7	1.3179 (17)	C10—C11	1.385 (2)
O3—H6	0.8200	C10—H2A	0.9300
O4—C7	1.2199 (19)	C11—C12	1.387 (3)
O5—C14	1.250 (2)	C11—C14	1.481 (2)
O6—C14	1.281 (2)	C12—C13	1.384 (2)
O6—H3	0.8200	C12—H6A	0.9300
O7—C21	1.286 (2)	C13—H5A	0.9300
O7—H8	0.8200	C15—C20	1.383 (2)
O8—C21	1.254 (2)	C15—C16	1.392 (2)
C1—C6	1.385 (2)	C16—C17	1.379 (2)
C1—C2	1.385 (2)	C16—H17A	0.9300
C2—C3	1.376 (2)	C17—C18	1.391 (2)
C2—H11A	0.9300	C17—H16A	0.9300
C3—C4	1.385 (2)	C18—C19	1.392 (2)
C4—C5	1.384 (2)	C18—C21	1.476 (2)
C4—H9A	0.9300	C19—C20	1.384 (2)
C5—C6	1.396 (2)	C19—H20A	0.9300
C5—C7	1.493 (2)	C20—H19A	0.9300
C6—H13A	0.9300

C1—O1—C8	119.01 (12)	C9—C10—H2A	119.9
C15—O2—C3	119.45 (12)	C10—C11—C12	119.59 (16)
C7—O3—H6	109.5	C10—C11—C14	120.24 (17)
C14—O6—H3	109.5	C12—C11—C14	120.17 (15)
C21—O7—H8	109.5	C13—C12—C11	120.33 (18)
O1—C1—C6	123.82 (14)	C13—C12—H6A	119.8
O1—C1—C2	114.92 (13)	C11—C12—H6A	119.8
C6—C1—C2	121.25 (14)	C8—C13—C12	119.21 (19)
C3—C2—C1	119.18 (14)	C8—C13—H5A	120.4
C3—C2—H11A	120.4	C12—C13—H5A	120.4
C1—C2—H11A	120.4	O5—C14—O6	123.49 (16)
C2—C3—C4	121.42 (14)	O5—C14—C11	120.18 (15)
C2—C3—O2	117.55 (13)	O6—C14—C11	116.32 (16)
C4—C3—O2	120.84 (13)	O2—C15—C20	123.41 (14)
C5—C4—C3	118.45 (13)	O2—C15—C16	115.32 (14)
C5—C4—H9A	120.8	C20—C15—C16	121.14 (14)
C3—C4—H9A	120.8	C17—C16—C15	119.03 (16)
C4—C5—C6	121.50 (14)	C17—C16—H17A	120.5
C4—C5—C7	120.94 (13)	C15—C16—H17A	120.5
C6—C5—C7	117.54 (14)	C16—C17—C18	120.92 (15)
C1—C6—C5	118.17 (14)	C16—C17—H16A	119.5
C1—C6—H13A	120.9	C18—C17—H16A	119.5
C5—C6—H13A	120.9	C17—C18—C19	119.00 (14)
O4—C7—O3	123.42 (14)	C17—C18—C21	121.08 (14)
O4—C7—C5	122.71 (13)	C19—C18—C21	119.84 (15)
O3—C7—C5	113.86 (13)	C20—C19—C18	120.88 (16)
C13—C8—C9	121.61 (16)	C20—C19—H20A	119.6
C13—C8—O1	118.08 (19)	C18—C19—H20A	119.6
C9—C8—O1	120.15 (18)	C15—C20—C19	119.02 (15)
C8—C9—C10	118.97 (17)	C15—C20—H19A	120.5
C8—C9—H3A	120.5	C19—C20—H19A	120.5
C10—C9—H3A	120.5	O8—C21—O7	122.91 (15)
C11—C10—C9	120.25 (19)	O8—C21—C18	120.30 (14)
C11—C10—H2A	119.9	O7—C21—C18	116.78 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O4ⁱ	0.82	1.87	2.6919 (16)	176.4
O6—H3···O8ⁱⁱ	0.82	1.85	2.6615 (18)	169.9
O7—H8···O5ⁱⁱⁱ	0.82	1.82	2.6307 (18)	167.2

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄O₈
M_r	394.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.235 (3), 13.419 (3), 15.586 (3)
β (°)	96.24 (3)
V (Å³)	3583.3 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.29 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.316, 0.622
No. of measured, independent and observed [I > 2σ(I)] reflections	16922, 4073, 2862
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.09
No. of reflections	4073
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.22

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXP97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O4ⁱ	0.82	1.87	2.6919 (16)	176.4
O6—H3···O8ⁱⁱ	0.82	1.85	2.6615 (18)	169.9
O7—H8···O5ⁱⁱⁱ	0.82	1.82	2.6307 (18)	167.2

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

Acknowledgements

The authors thank the National Natural Science Foundation of China.

References

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