Biphenyl-2,2′,4,4′-tetra­carb­oxy­lic acid monohydrate

Bu, D.; Zhang, A.; Zhao, D.

doi:10.1107/S1600536810037438

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2626

doi:10.1107/S1600536810037438

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Biphenyl-2,2′,4,4′-tetracarboxylic acid monohydrate

Dong Bu,^a Ai-yun Zhang ^a ^* and Dan Zhao ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: zay@hpu.edu.cn

(Received 11 August 2010; accepted 18 September 2010; online 25 September 2010)

In the title compound, C₁₆H₁₀O₈·H₂O, the dihedral angle between the two benzene rings is 71.63 (5)°. In the crystal structure, pairs of inversion-related molecules are stacked [mean interplanar spacing = 3.5195 (18) Å], and O—H⋯O and C—H⋯O hydrogen bonds create a three-dimensional network.

Related literature

For general background to the use of aromatic carboxylates as building blocks for the construction of various architectures, see: Li et al. (2008 ); Du et al. (2007 ). For previous studies on the synthesis of aromatic carboxylate hydrates, see: Jiang et al. (2008 ); Li et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₀O₈·H₂O
M_r = 348.26
Triclinic, $[P \overline 1]$
a = 7.1765 (1) Å
b = 9.4677 (2) Å
c = 11.9301 (2) Å
α = 106.013 (1)°
β = 100.098 (1)°
γ = 96.753 (1)°
V = 755.18 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.972, T_max = 0.976
13177 measured reflections
2663 independent reflections
2441 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.03
2663 reflections
236 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O9	0.82	1.79	2.6076 (18)	174
O1—H1A⋯O2ⁱ	0.82	1.87	2.680 (2)	169
O3—H3A⋯O4ⁱⁱ	0.82	1.84	2.6400 (17)	166
O7—H7A⋯O5ⁱⁱⁱ	0.82	1.82	2.6280 (17)	171
O9—H9B⋯O8^iv	0.85 (1)	1.92 (1)	2.7616 (19)	170 (2)
O9—H9A⋯O8^v	0.84 (1)	2.20 (1)	2.983 (2)	154 (2)
C12—H12⋯O3^vi	0.93	2.57	3.451 (2)	159
Symmetry codes: (i) -x+2, -y+3, -z+1; (ii) -x, -y+2, -z+1; (iii) x, y-1, z; (iv) -x, -y+2, -z+2; (v) x, y+1, z; (vi) -x+1, -y+2, -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 I, global. DOI: 10.1107/S1600536810037438/pk2260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037438/pk2260Isup2.hkl

checkCIF report

Comment top

Aromatic carboxylates have been proven to be effective building blocks in constructing various architectures (Li et al., 2008; Du et al., 2007). Many crystal structures of aromatic carboxylic hydrates have been reported (Jiang et al., 2008; Li et al., 2009). In this paper, we report the synthesis and structure of a new aromatic carboxylic hydrate, biphenyl-2, 2', 4, 4' -tetracarboxylic acid monohydrate, (Fig. 1).

The dihedral angle between the two benzene rings of biphenyl-2, 2', 4, 4' -tetracarboxylic acid monohydrate is 71.63 (5)°, which is markedly different from 42.30 (11)° found in the biphenyl-2, 3, 3', 4'-tetracarboxylic acid monohydrate (Jiang et al., 2008). This might be a result of the hydrogen bonding ineractions of the title compound. The lattice water molecule links with biphenyl-2, 2', 4, 4'-tetracarboxylic acid via O—H···O hydrogen bonding. The extensive O—H···O hydrogen bonding and a weak intermolecular C—H···O hydrogen bond helps to stabilize the crystal structure (Fig. 2 and Table 1). In addition, pairs of inversion related molecules are stacked with mean interplanar spacing = 3.5195 (18)Å)

Related literature top

For general background to the use of aromatic carboxylates as building blocks, see: Li et al. (2008); Du et al. (2007). For previous studies on the synthesis of aromatic carboxylate hydrates, see: Jiang et al. (2008); Li et al. (2009).

Experimental top

A mixture of C₁₆H₁₀O₈ (0.3360 g), BaCl₂ (0.3451 g) and water (12 ml) was stirred at room temperature for 6 h. The solution was filtered and the filtrate was left to stand undisturbed. Upon slow evaporation at room temperature, a colorless crystalline solid appeared about a month later. The resulting colorless blocks were filtered off washed with water and dried at ambient temperature.

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 structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level
	Fig. 2. The O···H—O and C—H···O hydrogen bonds of biphenyl-2, 2', 4, 4' -tetracarboxylic acid monhydrate.

Biphenyl-2,2',4,4'-tetracarboxylic acid monohydrate top

Crystal data top

C₁₆H₁₀O₈·H₂O	Z = 2
M_r = 348.26	F(000) = 360
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1765 (1) Å	Cell parameters from 9316 reflections
b = 9.4677 (2) Å	θ = 2.8–27.5°
c = 11.9301 (2) Å	µ = 0.13 mm⁻¹
α = 106.013 (1)°	T = 296 K
β = 100.098 (1)°	Block, yellow
γ = 96.753 (1)°	0.22 × 0.20 × 0.19 mm
V = 755.18 (2) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.972, T_max = 0.976	k = −11→11
13177 measured reflections	l = −14→14

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) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0701P)² + 0.3599P] where P = (F_o² + 2F_c²)/3
2663 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.22 e Å⁻³
3 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₆H₁₀O₈·H₂O	γ = 96.753 (1)°
M_r = 348.26	V = 755.18 (2) Å³
Triclinic, P1	Z = 2
a = 7.1765 (1) Å	Mo Kα radiation
b = 9.4677 (2) Å	µ = 0.13 mm⁻¹
c = 11.9301 (2) Å	T = 296 K
α = 106.013 (1)°	0.22 × 0.20 × 0.19 mm
β = 100.098 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2663 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2441 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.976	R_int = 0.019
13177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.22 e Å⁻³
2663 reflections	Δρ_min = −0.41 e Å⁻³
236 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	0.7651 (3)	1.4462 (2)	0.51405 (19)	0.0815 (6)
H1A	0.8362	1.4851	0.4799	0.122*
O2	1.0447 (2)	1.4309 (2)	0.61981 (17)	0.0734 (5)
O3	0.19262 (18)	1.12724 (18)	0.49778 (13)	0.0522 (4)
H3A	0.0770	1.0941	0.4759	0.078*
O4	0.17196 (18)	0.97698 (17)	0.60878 (13)	0.0518 (4)
O5	0.3535 (2)	1.20930 (14)	0.88045 (14)	0.0531 (4)
O6	0.1817 (2)	1.07466 (14)	0.96298 (13)	0.0448 (3)
H6A	0.1502	1.1551	0.9916	0.067*
O7	0.4508 (2)	0.46084 (14)	0.83504 (15)	0.0531 (4)
H7A	0.4132	0.3873	0.8539	0.080*
O8	0.2313 (2)	0.55361 (14)	0.92899 (13)	0.0474 (4)
O9	0.1086 (2)	1.34013 (16)	1.05603 (16)	0.0556 (4)
C1	0.7674 (2)	1.1428 (2)	0.77090 (16)	0.0376 (4)
H1	0.8355	1.1113	0.8306	0.045*
C2	0.8611 (3)	1.2492 (2)	0.73154 (17)	0.0398 (4)
H2	0.9908	1.2877	0.7640	0.048*
C3	0.7614 (2)	1.29848 (19)	0.64325 (15)	0.0341 (4)
C4	0.5674 (2)	1.24238 (18)	0.59864 (14)	0.0308 (4)
H4	0.4990	1.2783	0.5419	0.037*
C5	0.4723 (2)	1.13359 (17)	0.63672 (13)	0.0273 (3)
C6	0.5744 (2)	1.08125 (17)	0.72423 (14)	0.0283 (4)
C7	0.4997 (2)	0.95149 (17)	0.76245 (14)	0.0278 (3)
C8	0.3751 (2)	0.95295 (17)	0.84121 (14)	0.0275 (3)
C9	0.3250 (2)	0.82523 (17)	0.87296 (14)	0.0288 (4)
H9	0.2409	0.8259	0.9241	0.035*
C10	0.3984 (2)	0.69691 (17)	0.82967 (14)	0.0298 (4)
C11	0.5231 (3)	0.69593 (18)	0.75326 (15)	0.0346 (4)
H11	0.5729	0.6103	0.7236	0.041*
C12	0.5734 (2)	0.82211 (19)	0.72119 (15)	0.0337 (4)
H12	0.6588	0.8206	0.6707	0.040*
C13	0.8643 (3)	1.4007 (2)	0.59059 (18)	0.0441 (5)
C14	0.2659 (2)	1.07440 (18)	0.57925 (14)	0.0289 (4)
C15	0.3025 (2)	1.09080 (18)	0.89507 (15)	0.0305 (4)
C16	0.3493 (2)	0.56452 (18)	0.86928 (15)	0.0326 (4)
H9B	0.0046 (19)	1.370 (2)	1.0685 (19)	0.049*
H9A	0.177 (2)	1.4042 (19)	1.037 (2)	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0562 (10)	0.1074 (15)	0.0975 (14)	−0.0142 (10)	0.0034 (9)	0.0776 (12)
O2	0.0451 (9)	0.0946 (13)	0.0903 (13)	−0.0128 (8)	0.0080 (8)	0.0581 (11)
O3	0.0305 (7)	0.0725 (10)	0.0609 (9)	−0.0063 (6)	−0.0048 (6)	0.0472 (8)
O4	0.0309 (7)	0.0645 (9)	0.0665 (9)	−0.0116 (6)	−0.0020 (6)	0.0463 (8)
O5	0.0791 (10)	0.0269 (7)	0.0717 (10)	0.0150 (6)	0.0410 (8)	0.0268 (6)
O6	0.0483 (8)	0.0325 (7)	0.0667 (9)	0.0130 (6)	0.0330 (7)	0.0210 (6)
O7	0.0648 (9)	0.0334 (7)	0.0836 (10)	0.0199 (7)	0.0408 (8)	0.0341 (7)
O8	0.0514 (8)	0.0381 (7)	0.0709 (9)	0.0136 (6)	0.0310 (7)	0.0326 (7)
O9	0.0501 (9)	0.0410 (8)	0.0905 (11)	0.0181 (6)	0.0342 (8)	0.0280 (8)
C1	0.0303 (9)	0.0426 (10)	0.0421 (9)	−0.0012 (7)	0.0001 (7)	0.0243 (8)
C2	0.0291 (9)	0.0432 (10)	0.0462 (10)	−0.0070 (7)	0.0026 (7)	0.0210 (8)
C3	0.0327 (9)	0.0336 (9)	0.0372 (9)	−0.0034 (7)	0.0087 (7)	0.0158 (7)
C4	0.0323 (9)	0.0319 (8)	0.0319 (8)	0.0013 (7)	0.0071 (7)	0.0172 (7)
C5	0.0268 (8)	0.0283 (8)	0.0293 (8)	0.0022 (6)	0.0083 (6)	0.0125 (6)
C6	0.0290 (8)	0.0278 (8)	0.0306 (8)	0.0020 (6)	0.0081 (6)	0.0130 (6)
C7	0.0270 (8)	0.0286 (8)	0.0292 (8)	0.0011 (6)	0.0027 (6)	0.0147 (6)
C8	0.0264 (8)	0.0256 (8)	0.0328 (8)	0.0024 (6)	0.0051 (6)	0.0144 (6)
C9	0.0288 (8)	0.0274 (8)	0.0350 (8)	0.0029 (6)	0.0103 (6)	0.0156 (6)
C10	0.0315 (8)	0.0252 (8)	0.0349 (8)	0.0028 (6)	0.0063 (7)	0.0142 (6)
C11	0.0409 (9)	0.0277 (8)	0.0401 (9)	0.0095 (7)	0.0136 (7)	0.0138 (7)
C12	0.0378 (9)	0.0340 (9)	0.0356 (9)	0.0068 (7)	0.0148 (7)	0.0164 (7)
C13	0.0344 (10)	0.0508 (11)	0.0503 (11)	−0.0077 (8)	0.0054 (8)	0.0289 (9)
C14	0.0274 (8)	0.0321 (8)	0.0310 (8)	0.0028 (6)	0.0075 (6)	0.0159 (6)
C15	0.0309 (8)	0.0277 (8)	0.0371 (8)	0.0049 (6)	0.0078 (7)	0.0165 (7)
C16	0.0337 (9)	0.0264 (8)	0.0422 (9)	0.0048 (6)	0.0097 (7)	0.0170 (7)

Geometric parameters (Å, º) top

O1—C13	1.260 (2)	C3—C4	1.384 (2)
O1—H1A	0.8200	C3—C13	1.486 (2)
O2—C13	1.256 (2)	C4—C5	1.391 (2)
O3—C14	1.274 (2)	C4—H4	0.9300
O3—H3A	0.8200	C5—C6	1.405 (2)
O4—C14	1.243 (2)	C5—C14	1.489 (2)
O5—C15	1.207 (2)	C6—C7	1.498 (2)
O6—C15	1.309 (2)	C7—C12	1.391 (2)
O6—H6A	0.8200	C7—C8	1.405 (2)
O7—C16	1.309 (2)	C8—C9	1.390 (2)
O7—H7A	0.8200	C8—C15	1.484 (2)
O8—C16	1.211 (2)	C9—C10	1.385 (2)
O9—H9B	0.852 (9)	C9—H9	0.9300
O9—H9A	0.843 (9)	C10—C11	1.384 (2)
C1—C2	1.378 (2)	C10—C16	1.483 (2)
C1—C6	1.389 (2)	C11—C12	1.380 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.387 (3)	C12—H12	0.9300
C2—H2	0.9300

C13—O1—H1A	109.5	C9—C8—C15	119.43 (14)
C14—O3—H3A	109.5	C7—C8—C15	120.93 (14)
C15—O6—H6A	109.5	C10—C9—C8	121.11 (15)
C16—O7—H7A	109.5	C10—C9—H9	119.4
H9B—O9—H9A	109.6 (14)	C8—C9—H9	119.4
C2—C1—C6	122.08 (16)	C11—C10—C9	119.36 (14)
C2—C1—H1	119.0	C11—C10—C16	120.69 (15)
C6—C1—H1	119.0	C9—C10—C16	119.91 (15)
C1—C2—C3	119.76 (16)	C12—C11—C10	119.95 (15)
C1—C2—H2	120.1	C12—C11—H11	120.0
C3—C2—H2	120.1	C10—C11—H11	120.0
C4—C3—C2	119.01 (15)	C11—C12—C7	121.64 (15)
C4—C3—C13	120.32 (16)	C11—C12—H12	119.2
C2—C3—C13	120.49 (16)	C7—C12—H12	119.2
C3—C4—C5	121.54 (15)	O2—C13—O1	123.66 (18)
C3—C4—H4	119.2	O2—C13—C3	118.64 (17)
C5—C4—H4	119.2	O1—C13—C3	117.59 (16)
C4—C5—C6	119.40 (14)	O4—C14—O3	122.26 (15)
C4—C5—C14	117.74 (14)	O4—C14—C5	121.23 (14)
C6—C5—C14	122.84 (14)	O3—C14—C5	116.51 (14)
C1—C6—C5	118.14 (14)	O5—C15—O6	122.33 (16)
C1—C6—C7	115.96 (14)	O5—C15—C8	123.22 (15)
C5—C6—C7	125.51 (14)	O6—C15—C8	114.42 (14)
C12—C7—C8	118.34 (14)	O8—C16—O7	123.12 (15)
C12—C7—C6	115.43 (14)	O8—C16—C10	124.19 (15)
C8—C7—C6	126.07 (14)	O7—C16—C10	112.68 (14)
C9—C8—C7	119.59 (15)

C6—C1—C2—C3	0.5 (3)	C8—C9—C10—C11	−0.2 (2)
C1—C2—C3—C4	1.7 (3)	C8—C9—C10—C16	177.30 (15)
C1—C2—C3—C13	−173.46 (18)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−2.7 (3)	C16—C10—C11—C12	−177.33 (16)
C13—C3—C4—C5	172.56 (16)	C10—C11—C12—C7	−0.9 (3)
C3—C4—C5—C6	1.3 (2)	C8—C7—C12—C11	1.7 (2)
C3—C4—C5—C14	−176.96 (15)	C6—C7—C12—C11	177.43 (15)
C2—C1—C6—C5	−1.9 (3)	C4—C3—C13—O2	−168.9 (2)
C2—C1—C6—C7	171.29 (17)	C2—C3—C13—O2	6.2 (3)
C4—C5—C6—C1	1.0 (2)	C4—C3—C13—O1	7.5 (3)
C14—C5—C6—C1	179.14 (15)	C2—C3—C13—O1	−177.4 (2)
C4—C5—C6—C7	−171.49 (15)	C4—C5—C14—O4	179.96 (16)
C14—C5—C6—C7	6.6 (2)	C6—C5—C14—O4	1.8 (3)
C1—C6—C7—C12	−67.3 (2)	C4—C5—C14—O3	0.9 (2)
C5—C6—C7—C12	105.40 (19)	C6—C5—C14—O3	−177.24 (16)
C1—C6—C7—C8	108.06 (19)	C9—C8—C15—O5	173.05 (17)
C5—C6—C7—C8	−79.3 (2)	C7—C8—C15—O5	−4.3 (3)
C12—C7—C8—C9	−1.7 (2)	C9—C8—C15—O6	−5.2 (2)
C6—C7—C8—C9	−176.93 (15)	C7—C8—C15—O6	177.43 (15)
C12—C7—C8—C15	175.65 (15)	C11—C10—C16—O8	−174.54 (17)
C6—C7—C8—C15	0.5 (2)	C9—C10—C16—O8	8.0 (3)
C7—C8—C9—C10	1.0 (2)	C11—C10—C16—O7	6.9 (2)
C15—C8—C9—C10	−176.42 (14)	C9—C10—C16—O7	−170.53 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O9	0.82	1.79	2.6076 (18)	174
C4—H4···O3	0.93	2.37	2.706 (2)	101
C9—H9···O6	0.93	2.38	2.711 (2)	101
O1—H1A···O2ⁱ	0.82	1.87	2.680 (2)	169
O3—H3A···O4ⁱⁱ	0.82	1.84	2.6400 (17)	166
O7—H7A···O5ⁱⁱⁱ	0.82	1.82	2.6280 (17)	171
O9—H9B···O8^iv	0.85 (1)	1.92 (1)	2.7616 (19)	170 (2)
O9—H9A···O8^v	0.84 (1)	2.20 (1)	2.983 (2)	154 (2)
C12—H12···O3^vi	0.93	2.57	3.451 (2)	159

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀O₈·H₂O
M_r	348.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1765 (1), 9.4677 (2), 11.9301 (2)
α, β, γ (°)	106.013 (1), 100.098 (1), 96.753 (1)
V (Å³)	755.18 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.972, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	13177, 2663, 2441
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.03
No. of reflections	2663
No. of parameters	236
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.41

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
O6—H6A···O9	0.82	1.79	2.6076 (18)	173.6
C4—H4···O3	0.93	2.37	2.706 (2)	101.3
C9—H9···O6	0.93	2.38	2.711 (2)	101.0
O1—H1A···O2ⁱ	0.82	1.87	2.680 (2)	169.1
O3—H3A···O4ⁱⁱ	0.82	1.84	2.6400 (17)	165.8
O7—H7A···O5ⁱⁱⁱ	0.82	1.82	2.6280 (17)	170.8
O9—H9B···O8^iv	0.852 (9)	1.918 (11)	2.7616 (19)	170 (2)
O9—H9A···O8^v	0.843 (9)	2.202 (13)	2.983 (2)	154 (2)
C12—H12···O3^vi	0.93	2.57	3.451 (2)	158.7

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

Acknowledgements

We thank the Universities and Colleges Natural Science Foundation of Henan (2009 A150011) and the Natural Science Foundation of China (200903036) for support.

References

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