Poly[[hexa­aqua­(μ2-fumarato-κ4O1,O1′:O4,O4′)bis­(μ3-maleato-κ4O1,O1′:O4:O4′)disamarium(III)] hexa­hydrate]

Li, B.; Wu, L.-X.

doi:10.1107/S1600536810045204

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1540

https://doi.org/10.1107/S1600536810045204

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Poly[[hexaaqua(μ₂-fumarato-κ⁴O¹,O^1′:O⁴,O^4′)bis(μ₃-maleato-κ⁴O¹,O^1′:O⁴:O^4′)disamarium(III)] hexahydrate]

Bao Li ^a and Li-Xin Wu ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: wulx@jlu.edu.cn

(Received 5 October 2010; accepted 4 November 2010; online 10 November 2010)

In the title coordination polymer, {[Sm₂(C₄H₂O₄)₃(H₂O)₆]·6H₂O}_n, the Sm^III ion is nine-coordinated by four O atoms from three different maleate ligands, two O atoms from one fumarate ligand and three O atoms from three water molecules. The fumarate ligand lies on an inversion center. Adjacent Sm^III ions are bridged by the maleate and fumarate ligands, forming a layer parallel to (011). The layers are further linked by intermolecular O—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Related literature

For the structures of transition metal complexes with malonate ligands, see: Li et al. (2006 ); Ye et al. (2007 ); Zhu et al. (2007 ). For a related structure, see: Hansson & Thörnqwist (1975 ).

Experimental

Crystal data

[Sm₂(C₄H₂O₄)₃(H₂O)₆]·6H₂O
M_r = 859.08
Triclinic, $[P \overline 1]$
a = 6.150 (3) Å
b = 10.679 (6) Å
c = 11.214 (6) Å
α = 69.99 (3)°
β = 79.64 (2)°
γ = 89.74 (2)°
V = 679.4 (6) Å³
Z = 1
Mo Kα radiation
μ = 4.38 mm⁻¹
T = 290 K
0.08 × 0.07 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.732, T_max = 0.782
6707 measured reflections
3071 independent reflections
2950 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.066
S = 1.00
3071 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O6ⁱ	0.85	1.88	2.680 (4)	156
O7—H7A⋯O11ⁱⁱ	0.85	1.95	2.774 (5)	164
O8—H8A⋯O11ⁱⁱⁱ	0.85	1.94	2.770 (5)	164
O8—H8B⋯O10ⁱⁱ	0.85	1.97	2.792 (5)	164
O9—H9A⋯O7^iv	0.85	2.10	2.893 (4)	155
O9—H9B⋯O3^iv	0.85	1.97	2.808 (4)	168
O10—H10A⋯O1^v	0.85	1.97	2.783 (4)	160
O10—H10B⋯O12	0.85	1.95	2.761 (5)	159
O11—H11B⋯O12	0.85	1.93	2.775 (5)	171
O11—H11A⋯O10^iv	0.85	1.95	2.755 (5)	157
O12—H12A⋯O4^vi	0.85	1.87	2.705 (5)	168
O12—H12B⋯O5ⁱⁱ	0.89	1.98	2.744 (5)	142
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z; (iv) x-1, y, z; (v) x, y-1, z; (vi) -x+2, -y+2, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045204/hy2363sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045204/hy2363Isup2.hkl

checkCIF report

Comment top

Diacids have been widely used to form metal–organic frameworks. Recently, we reported several compounds based on malonate ligand and different transition metal ions (Li et al., 2006; Ye et al., 2007; Zhu et al., 2007). Hererin, we report the crystal structure of the title compound based on maleate ligand.

The structure of the title compound is shown in Fig. 1. The bond lengths and angles are normal and comparable with those reported for a similar structure (Hansson & Thörnqwist, 1975). The Sm^III ion is nine-coordinated by four O atoms from three maleate ligands, two O atoms from one fumarate ligand and three coordinated water molecules. The two carboxylate groups of the fumarate ligand and one of the carboxylate groups of the maleate ligand exhibit a chelating coordination mode, while the other carboxylate group of the maleate ligand binds Sm^III ions in a bidentate bridging mode. Adjacent Sm^III ions are bridged by the maleate and fumarate ligands, forming a layer parallel to (0 1 1) (Fig. 2). Additionly, abundant O—H···O hydrogen bonds stabilize the crystal structure of the title compound (Table 1).

Related literature top

For the structures of transition metal complexes with malonate ligands, see: Li et al. (2006); Ye et al. (2007); Zhu et al. (2007). For a related structure, see: Hansson & Thörnqwist (1975).

Experimental top

Maleic acid and Sm(NO₃)₃ of analytical grade are used without further purification. Sm(NO₃)₃ (67.24 mg, 0.2 mmol) and maleic acid (69.64 mg, 0.6 mmol) were dissolved in water (10 ml), and the pH value was adjusted to about 3 using a dilute NaOH solution. The mixture was stirred for half an hour and then filtered. The filtrate was allowed to stand at room temperature for two weeks, giving colorless block-shaped crystals.

Structure description top

For the structures of transition metal complexes with malonate ligands, see: Li et al. (2006); Ye et al. (2007); Zhu et al. (2007). For a related structure, see: Hansson & Thörnqwist (1975).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with the symmetry-related atoms to complete the Sm coordination. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry codes: (A) -x, 1-y, 1-z; (B) 2-x, 2-y, -z; (C) 1+x, y, z; (D) 1-x, 2-y, -z.]
	Fig. 2. Crystal packing diagram of the title cmopound, showing the two-dimensional network.

Poly[[hexaaqua(µ₂-fumarato- κ⁴O¹,O^1':O⁴,O^4')bis(µ₃-maleato- κ⁴O¹,O^1':O⁴:O^4')disamarium(III)] hexahydrate] top

Crystal data top

[Sm₂(C₄H₂O₄)₃(H₂O)₆]·6H₂O	Z = 1
M_r = 859.08	F(000) = 418
Triclinic, P1	D_x = 2.100 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.150 (3) Å	Cell parameters from 6497 reflections
b = 10.679 (6) Å	θ = 3.3–27.5°
c = 11.214 (6) Å	µ = 4.38 mm⁻¹
α = 69.99 (3)°	T = 290 K
β = 79.64 (2)°	Block, colorless
γ = 89.74 (2)°	0.08 × 0.07 × 0.06 mm
V = 679.4 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3071 independent reflections
Radiation source: rotation anode	2950 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
T_min = 0.732, T_max = 0.782	k = −13→13
6707 measured reflections	l = −14→13

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0342P)² + 3.0041P] where P = (F_o² + 2F_c²)/3
3071 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Sm₂(C₄H₂O₄)₃(H₂O)₆]·6H₂O	γ = 89.74 (2)°
M_r = 859.08	V = 679.4 (6) Å³
Triclinic, P1	Z = 1
a = 6.150 (3) Å	Mo Kα radiation
b = 10.679 (6) Å	µ = 4.38 mm⁻¹
c = 11.214 (6) Å	T = 290 K
α = 69.99 (3)°	0.08 × 0.07 × 0.06 mm
β = 79.64 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3071 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2950 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.782	R_int = 0.018
6707 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
3071 reflections	Δρ_min = −0.58 e Å⁻³
172 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6917 (6)	1.1675 (4)	0.0453 (3)	0.0173 (7)
C2	0.7911 (7)	1.3067 (4)	0.0028 (4)	0.0256 (8)
H2	0.7026	1.3681	0.0269	0.031*
C3	0.9922 (7)	1.3525 (4)	−0.0657 (4)	0.0291 (9)
H3	1.0311	1.4423	−0.0853	0.035*
C4	1.1596 (6)	1.2717 (4)	−0.1134 (3)	0.0190 (7)
C5	0.2343 (6)	0.6379 (4)	0.4136 (3)	0.0176 (7)
C6	0.0980 (7)	0.5175 (4)	0.5083 (4)	0.0254 (8)
H6	0.1523	0.4658	0.5807	0.031*
O1	0.6917 (5)	1.0926 (3)	0.1584 (3)	0.0230 (6)
O2	0.6003 (5)	1.1329 (4)	−0.0303 (3)	0.0321 (7)
O3	1.1332 (4)	1.1467 (3)	−0.0770 (3)	0.0211 (5)
O4	1.3316 (5)	1.3327 (3)	−0.1921 (3)	0.0326 (7)
O5	0.4186 (5)	0.6652 (3)	0.4363 (3)	0.0253 (6)
O6	0.1671 (4)	0.7103 (3)	0.3142 (3)	0.0224 (5)
O7	0.8126 (4)	0.8515 (3)	0.3427 (3)	0.0223 (5)
H7B	0.8962	0.7909	0.3325	0.033*
H7A	0.8156	0.8534	0.4176	0.033*
O8	0.3684 (5)	0.9438 (3)	0.4042 (3)	0.0289 (6)
H8A	0.3148	1.0200	0.3882	0.043*
H8B	0.3346	0.9100	0.4861	0.043*
O9	0.1952 (4)	1.0193 (3)	0.1778 (3)	0.0236 (6)
H9A	0.0669	0.9933	0.2236	0.035*
H9B	0.1633	1.0477	0.1027	0.035*
O10	0.8053 (6)	0.1975 (3)	0.3360 (3)	0.0339 (7)
H10A	0.7981	0.1545	0.2853	0.051*
H10B	0.7485	0.2727	0.3128	0.051*
O11	0.2212 (5)	0.1916 (3)	0.3961 (3)	0.0322 (7)
H11B	0.3085	0.2599	0.3771	0.048*
H11A	0.1137	0.2035	0.3560	0.048*
O12	0.5308 (6)	0.4066 (3)	0.3112 (3)	0.0384 (8)
H12A	0.5696	0.4872	0.2639	0.058*
H12B	0.5062	0.4142	0.3894	0.058*
Sm1	0.50414 (3)	0.869449 (17)	0.223642 (16)	0.01447 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0152 (16)	0.0201 (17)	0.0163 (16)	0.0006 (13)	0.0001 (12)	−0.0074 (13)
C2	0.028 (2)	0.0164 (17)	0.029 (2)	0.0044 (15)	0.0018 (16)	−0.0079 (15)
C3	0.035 (2)	0.0138 (17)	0.033 (2)	−0.0033 (15)	0.0089 (17)	−0.0089 (16)
C4	0.0210 (17)	0.0184 (16)	0.0152 (16)	−0.0009 (14)	−0.0014 (13)	−0.0038 (13)
C5	0.0164 (16)	0.0167 (16)	0.0163 (16)	0.0012 (13)	−0.0015 (13)	−0.0023 (13)
C6	0.0252 (19)	0.0207 (18)	0.0224 (18)	−0.0066 (15)	0.0005 (15)	0.0002 (15)
O1	0.0281 (14)	0.0196 (13)	0.0172 (12)	−0.0039 (11)	−0.0035 (11)	−0.0013 (10)
O2	0.0257 (15)	0.051 (2)	0.0247 (15)	−0.0029 (14)	−0.0051 (12)	−0.0194 (14)
O3	0.0207 (13)	0.0153 (12)	0.0247 (13)	−0.0003 (10)	−0.0003 (10)	−0.0055 (10)
O4	0.0282 (15)	0.0187 (14)	0.0409 (18)	−0.0034 (12)	0.0135 (13)	−0.0076 (13)
O5	0.0186 (13)	0.0246 (14)	0.0274 (14)	−0.0048 (11)	−0.0072 (11)	−0.0006 (11)
O6	0.0169 (12)	0.0215 (13)	0.0219 (13)	−0.0008 (10)	−0.0043 (10)	0.0017 (10)
O7	0.0154 (12)	0.0271 (14)	0.0234 (13)	0.0044 (10)	−0.0063 (10)	−0.0062 (11)
O8	0.0423 (17)	0.0262 (15)	0.0168 (13)	0.0084 (13)	−0.0019 (12)	−0.0074 (11)
O9	0.0168 (12)	0.0270 (14)	0.0216 (13)	0.0030 (11)	−0.0029 (10)	−0.0021 (11)
O10	0.0396 (18)	0.0385 (18)	0.0292 (16)	0.0048 (14)	−0.0105 (13)	−0.0168 (14)
O11	0.0342 (17)	0.0299 (16)	0.0337 (16)	0.0009 (13)	−0.0113 (13)	−0.0101 (13)
O12	0.051 (2)	0.0229 (15)	0.0373 (18)	−0.0064 (14)	−0.0083 (15)	−0.0057 (13)
Sm1	0.01201 (10)	0.01535 (10)	0.01502 (10)	−0.00140 (6)	−0.00158 (6)	−0.00444 (7)

Geometric parameters (Å, º) top

C1—O1	1.247 (5)	O9—H9A	0.8500
C1—O2	1.249 (5)	O9—H9B	0.8500
C1—C2	1.493 (5)	O10—H10A	0.8500
C2—C3	1.328 (6)	O10—H10B	0.8501
C2—H2	0.9300	O11—H11B	0.8500
C3—C4	1.484 (5)	O11—H11A	0.8500
C3—H3	0.9300	O12—H12A	0.8500
C4—O3	1.256 (5)	O12—H12B	0.8944
C4—O4	1.265 (5)	Sm1—O1	2.464 (3)
C5—O6	1.258 (5)	Sm1—O2ⁱⁱ	2.377 (3)
C5—O5	1.262 (5)	Sm1—O3ⁱⁱⁱ	2.566 (3)
C5—C6	1.496 (5)	Sm1—O4ⁱⁱⁱ	2.486 (3)
C6—C6ⁱ	1.327 (8)	Sm1—O5	2.593 (3)
C6—H6	0.9300	Sm1—O6	2.512 (3)
O7—H7B	0.8500	Sm1—O7	2.480 (3)
O7—H7A	0.8499	Sm1—O8	2.432 (3)
O8—H8A	0.8500	Sm1—O9	2.489 (3)
O8—H8B	0.8500

O1—C1—O2	122.4 (4)	O2ⁱⁱ—Sm1—O7	145.71 (10)
O1—C1—C2	118.2 (3)	O8—Sm1—O7	73.67 (10)
O2—C1—C2	119.2 (4)	O1—Sm1—O7	71.50 (10)
C3—C2—C1	127.1 (4)	O2ⁱⁱ—Sm1—O4ⁱⁱⁱ	76.01 (12)
C3—C2—H2	116.4	O8—Sm1—O4ⁱⁱⁱ	137.15 (11)
C1—C2—H2	116.4	O1—Sm1—O4ⁱⁱⁱ	126.86 (10)
C2—C3—C4	125.2 (4)	O7—Sm1—O4ⁱⁱⁱ	80.70 (11)
C2—C3—H3	117.4	O2ⁱⁱ—Sm1—O9	71.17 (11)
C4—C3—H3	117.4	O8—Sm1—O9	69.13 (10)
O3—C4—O4	120.7 (3)	O1—Sm1—O9	77.68 (10)
O3—C4—C3	121.5 (3)	O7—Sm1—O9	136.11 (10)
O4—C4—C3	117.7 (3)	O4ⁱⁱⁱ—Sm1—O9	143.16 (11)
O3—C4—Sm1ⁱⁱⁱ	62.2 (2)	O2ⁱⁱ—Sm1—O6	79.19 (10)
O4—C4—Sm1ⁱⁱⁱ	58.6 (2)	O8—Sm1—O6	84.11 (11)
C3—C4—Sm1ⁱⁱⁱ	175.8 (3)	O1—Sm1—O6	152.27 (10)
O6—C5—O5	120.8 (3)	O7—Sm1—O6	121.53 (9)
O6—C5—C6	121.1 (3)	O4ⁱⁱⁱ—Sm1—O6	80.77 (10)
O5—C5—C6	118.1 (3)	O9—Sm1—O6	77.11 (10)
C6ⁱ—C6—C5	121.8 (5)	O2ⁱⁱ—Sm1—O3ⁱⁱⁱ	74.78 (10)
C6ⁱ—C6—H6	119.1	O8—Sm1—O3ⁱⁱⁱ	140.72 (10)
C5—C6—H6	119.1	O1—Sm1—O3ⁱⁱⁱ	76.69 (9)
C1—O1—Sm1	115.9 (2)	O7—Sm1—O3ⁱⁱⁱ	71.03 (10)
C1—O2—Sm1ⁱⁱ	161.0 (3)	O4ⁱⁱⁱ—Sm1—O3ⁱⁱⁱ	51.38 (9)
C4—O3—Sm1ⁱⁱⁱ	92.2 (2)	O9—Sm1—O3ⁱⁱⁱ	130.71 (9)
C4—O4—Sm1ⁱⁱⁱ	95.7 (2)	O6—Sm1—O3ⁱⁱⁱ	129.48 (9)
C5—O5—Sm1	92.2 (2)	O2ⁱⁱ—Sm1—O5	121.78 (11)
C5—O6—Sm1	96.1 (2)	O8—Sm1—O5	70.25 (11)
Sm1—O7—H7B	110.4	O1—Sm1—O5	134.92 (9)
Sm1—O7—H7A	131.5	O7—Sm1—O5	70.75 (9)
H7B—O7—H7A	106.8	O4ⁱⁱⁱ—Sm1—O5	69.11 (11)
Sm1—O8—H8A	118.2	O9—Sm1—O5	115.51 (9)
Sm1—O8—H8B	137.9	O6—Sm1—O5	50.82 (9)
H8A—O8—H8B	102.8	O3ⁱⁱⁱ—Sm1—O5	112.47 (9)
Sm1—O9—H9A	118.7	O2ⁱⁱ—Sm1—C4ⁱⁱⁱ	74.35 (11)
Sm1—O9—H9B	120.7	O8—Sm1—C4ⁱⁱⁱ	146.16 (11)
H9A—O9—H9B	100.2	O1—Sm1—C4ⁱⁱⁱ	101.68 (11)
H10A—O10—H10B	113.0	O7—Sm1—C4ⁱⁱⁱ	73.74 (10)
H11B—O11—H11A	115.2	O4ⁱⁱⁱ—Sm1—C4ⁱⁱⁱ	25.73 (10)
H12A—O12—H12B	100.4	O9—Sm1—C4ⁱⁱⁱ	144.26 (10)
O2ⁱⁱ—Sm1—O8	139.41 (11)	O6—Sm1—C4ⁱⁱⁱ	105.51 (11)
O2ⁱⁱ—Sm1—O1	103.29 (11)	O3ⁱⁱⁱ—Sm1—C4ⁱⁱⁱ	25.66 (9)
O8—Sm1—O1	76.25 (10)	O5—Sm1—C4ⁱⁱⁱ	90.53 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O6^iv	0.85	1.88	2.680 (4)	156
O7—H7A···O11^v	0.85	1.95	2.774 (5)	164
O8—H8A···O11^vi	0.85	1.94	2.770 (5)	164
O8—H8B···O10^v	0.85	1.97	2.792 (5)	164
O9—H9A···O7^vii	0.85	2.10	2.893 (4)	155
O9—H9B···O3^vii	0.85	1.97	2.808 (4)	168
O10—H10A···O1^viii	0.85	1.97	2.783 (4)	160
O10—H10B···O12	0.85	1.95	2.761 (5)	159
O11—H11B···O12	0.85	1.93	2.775 (5)	171
O11—H11A···O10^vii	0.85	1.95	2.755 (5)	157
O12—H12A···O4ⁱⁱⁱ	0.85	1.87	2.705 (5)	168
O12—H12B···O5^v	0.89	1.98	2.744 (5)	142

Symmetry codes: (iii) −x+2, −y+2, −z; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) x−1, y, z; (viii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Sm₂(C₄H₂O₄)₃(H₂O)₆]·6H₂O
M_r	859.08
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	6.150 (3), 10.679 (6), 11.214 (6)
α, β, γ (°)	69.99 (3), 79.64 (2), 89.74 (2)
V (Å³)	679.4 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.38
Crystal size (mm)	0.08 × 0.07 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.732, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	6707, 3071, 2950
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.066, 1.00
No. of reflections	3071
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.58

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O6ⁱ	0.85	1.88	2.680 (4)	156
O7—H7A···O11ⁱⁱ	0.85	1.95	2.774 (5)	164
O8—H8A···O11ⁱⁱⁱ	0.85	1.94	2.770 (5)	164
O8—H8B···O10ⁱⁱ	0.85	1.97	2.792 (5)	164
O9—H9A···O7^iv	0.85	2.10	2.893 (4)	155
O9—H9B···O3^iv	0.85	1.97	2.808 (4)	168
O10—H10A···O1^v	0.85	1.97	2.783 (4)	160
O10—H10B···O12	0.85	1.95	2.761 (5)	159
O11—H11B···O12	0.85	1.93	2.775 (5)	171
O11—H11A···O10^iv	0.85	1.95	2.755 (5)	157
O12—H12A···O4^vi	0.85	1.87	2.705 (5)	168
O12—H12B···O5ⁱⁱ	0.89	1.98	2.744 (5)	142

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

Acknowledgements

This work was supported financially by the National Basic Research Program of China (grant No. 2007CB808003) and the National Natural Science Foundation of China (grant Nos. 20973082, 20921003, 20703019).

References

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