Tetra­aqua­bis(3,5-di-4-pyridyl-1H-1,2,4-triazolido)cadmium(II) dihydrate

Liu, T.-L.; Zhang, Y.-L.

doi:10.1107/S1600536809024908

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m913

doi:10.1107/S1600536809024908

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Tetraaquabis(3,5-di-4-pyridyl-1H-1,2,4-triazolido)cadmium(II) dihydrate

Ti-Lou Liu ^a ^* and Yun-Liang Zhang ^a

^aDepartment of Pharmacy, Shaoyang Medical College, Shaoyang, Hunan 422000, People's Republic of China
^*Correspondence e-mail: liutilou2009@163.com

(Received 18 June 2009; accepted 28 June 2009; online 11 July 2009)

In the title compound, [Cd(C₁₂H₈N₅)₂(H₂O)₄]·2H₂O, the Cd^II atom is located on an inversion center and is coordinated by the two N atoms [Cd—N = 2.278 (2) Å] and four O atoms [Cd—O = 2.304 (2)–2.322 (2) Å] in a distorted octahedral geometry. Intermolecular O—H⋯O and O—H⋯N hydrogen bonds link the complex into a three-dimensional supramolecular framework.

Related literature

For the properties of hydrogen bonds in biological systems, see: Deisenhofer & Michel (1989 ). For extended supramolecular structures, see: Beatty (2003 ); Li et al. (2006 ); Russell & Ward (1996 ). For comparitive bond distances, see: Wen et al. (2005 ); Fu et al. (2007 ).

Experimental

Crystal data

[Cd(C₁₂H₈N₅)₂(H₂O)₄]·2H₂O
M_r = 664.97
Monoclinic, P 2₁ /c
a = 7.5030 (15) Å
b = 15.748 (3) Å
c = 12.009 (2) Å
β = 106.68 (3)°
V = 1359.2 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.815, T_max = 0.911
9599 measured reflections
3101 independent reflections
2663 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.070
S = 1.01
3101 reflections
211 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2ⁱ	0.84 (2)	1.95 (3)	2.768 (3)	164 (3)
O1—H1B⋯O3	0.85 (3)	1.95 (3)	2.786 (3)	169 (3)
O2—H2A⋯N3ⁱⁱ	0.85 (3)	1.98 (3)	2.829 (3)	171 (3)
O2—H2B⋯O3ⁱⁱⁱ	0.85 (3)	1.95 (3)	2.758 (3)	161 (3)
O3—H3A⋯N4^iv	0.85 (3)	2.06 (2)	2.895 (3)	171 (3)
O3—H3B⋯N5^v	0.85 (3)	1.95 (2)	2.796 (3)	170 (3)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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/S1600536809024908/bg2273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024908/bg2273Isup2.hkl

checkCIF report

Comment top

The hydrogen bond interaction plays a important role in some biological systems (Deisenhofer & Michel, 1989). Supramolecular assembly through hydrogen bonds has been extensively exploited to generate extended one-, two- and three-dimensional structures (Beatty et al., 2003; Li et al., 2006; Russell & Ward, 1996). As part of this ongoing work, We present here the synthesis and structural characterization of the title cadmium complex, [Cd(C₁₂H₈N₅)₂(H₂O)₄].2H₂O, (I).

The molecule of the title complex, (Fig. 1), is centrosymmetric, so pairs of equivalent ligands lie trans to each other in a slightly distorted octahedral coordination geometry, cis angles deviating from 90° by less than 4°. with Cd—O bond length in the range 2.304 (2)–2.322 (2) Å and a Cd—N bond length of 2.278 (2) Å. These bond distances compare well with those in the literature (Wen et al., 2005; Fu et al., 2007). Molecules are linked by O—H···O and O—H···N hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the properties of hydrogen bonds in biological systems, see: Deisenhofer & Michel (1989). For extended supramolecular structures, see: Beatty et al. (2003); Li et al. (2006); Russell & Ward (1996). For comparitive bond distances; Wen et al. (2005); Fu et al. (2007).

Experimental top

Cd(NO₃)₂.4H₂O (0.5 mmol, 0.154 g), 1H-3,5-di(4-pyridyl)-1,2,4-triazole (0.5 mmol, 0.112 g), and water (12 ml) were placed in a 23-ml Teflon-lined Parr bomb. The bomb was heated at 453 K for 3 d. The colourless block-shapped crystals were filtered off and washed with water and acetone (yield 45%, based on Cd).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. A view of the molecular structure of (I) with the atom-numbering scheme and 30% displacement ellipsoids. Atoms with the suffix A are generated by the symmetry operation (-x, -y + 1, -z + 1).
	Fig. 2. The 3-D network of (I).

Tetraaquabis(3,5-di-4-pyridyl-1H-1,2,4-triazolido)cadmium(II) dihydrate top

Crystal data top

[Cd(C₁₂H₈N₅)₂(H₂O)₄]·2H₂O	F(000) = 676
M_r = 664.97	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2567 reflections
a = 7.5030 (15) Å	θ = 2.6–27.3°
b = 15.748 (3) Å	µ = 0.86 mm⁻¹
c = 12.009 (2) Å	T = 293 K
β = 106.68 (3)°	Block, colorless
V = 1359.2 (5) Å³	0.40 × 0.20 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3101 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.815, T_max = 0.911	k = −20→20
9599 measured reflections	l = −15→15

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0271P)² + P] where P = (F_o² + 2F_c²)/3
3101 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.30 e Å⁻³
9 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cd(C₁₂H₈N₅)₂(H₂O)₄]·2H₂O	V = 1359.2 (5) Å³
M_r = 664.97	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5030 (15) Å	µ = 0.86 mm⁻¹
b = 15.748 (3) Å	T = 293 K
c = 12.009 (2) Å	0.40 × 0.20 × 0.12 mm
β = 106.68 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3101 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2663 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.911	R_int = 0.035
9599 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	9 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.30 e Å⁻³
3101 reflections	Δρ_min = −0.47 e Å⁻³
211 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
Cd1	0.0000	0.5000	0.5000	0.02624 (8)
C1	0.0093 (4)	0.67991 (14)	0.3780 (2)	0.0362 (6)
H1	−0.0392	0.6476	0.3113	0.043*
C2	0.0355 (4)	0.76513 (14)	0.3660 (2)	0.0350 (5)
H2	0.0038	0.7894	0.2923	0.042*
C3	0.1089 (3)	0.81536 (13)	0.46302 (19)	0.0260 (5)
C4	0.1464 (4)	0.77542 (14)	0.5700 (2)	0.0371 (6)
H4	0.1919	0.8065	0.6382	0.045*
C5	0.1161 (4)	0.68949 (15)	0.5749 (2)	0.0380 (6)
H5	0.1430	0.6638	0.6476	0.046*
C6	0.1502 (3)	0.90502 (13)	0.45109 (18)	0.0265 (5)
C7	0.2512 (3)	1.02895 (14)	0.4805 (2)	0.0274 (5)
C8	0.3340 (3)	1.10850 (13)	0.53511 (19)	0.0276 (5)
C9	0.3496 (4)	1.17874 (16)	0.4689 (2)	0.0472 (7)
H9	0.3127	1.1754	0.3882	0.057*
C10	0.4202 (5)	1.25321 (16)	0.5236 (2)	0.0515 (8)
H10	0.4285	1.2995	0.4772	0.062*
C11	0.4620 (4)	1.19586 (16)	0.7006 (2)	0.0423 (6)
H11	0.5012	1.2010	0.7811	0.051*
C12	0.3919 (4)	1.11875 (15)	0.6541 (2)	0.0376 (6)
H12	0.3837	1.0738	0.7027	0.045*
H1A	0.081 (4)	0.4477 (19)	0.303 (2)	0.065 (11)*
H2A	0.251 (5)	0.487 (2)	0.722 (2)	0.076 (12)*
H3A	0.333 (4)	0.5708 (17)	0.2136 (15)	0.057 (10)*
H1B	0.225 (4)	0.5023 (14)	0.349 (3)	0.050 (9)*
H2B	0.371 (3)	0.474 (2)	0.656 (3)	0.071 (11)*
H3B	0.419 (4)	0.6266 (12)	0.301 (2)	0.059 (9)*
N1	0.0504 (3)	0.64121 (11)	0.48107 (16)	0.0309 (4)
N2	0.1075 (3)	0.94209 (12)	0.34725 (16)	0.0338 (5)
N3	0.1745 (3)	1.02282 (12)	0.36636 (17)	0.0351 (5)
N4	0.2401 (3)	0.95673 (11)	0.53920 (16)	0.0269 (4)
N5	0.4772 (3)	1.26344 (13)	0.6379 (2)	0.0413 (5)
O1	0.1563 (3)	0.46448 (12)	0.36541 (15)	0.0358 (4)
O2	0.2657 (3)	0.49379 (12)	0.65460 (16)	0.0416 (4)
O3	0.3821 (3)	0.57563 (10)	0.28626 (15)	0.0349 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03522 (14)	0.01796 (11)	0.02429 (13)	−0.00424 (9)	0.00655 (10)	−0.00067 (8)
C1	0.0537 (16)	0.0256 (11)	0.0261 (12)	−0.0094 (11)	0.0063 (11)	−0.0044 (9)
C2	0.0516 (15)	0.0269 (11)	0.0240 (11)	−0.0059 (11)	0.0067 (11)	0.0028 (9)
C3	0.0296 (11)	0.0208 (10)	0.0275 (11)	−0.0013 (8)	0.0079 (9)	0.0014 (8)
C4	0.0577 (16)	0.0233 (11)	0.0255 (12)	−0.0090 (11)	0.0042 (12)	−0.0027 (9)
C5	0.0596 (17)	0.0254 (11)	0.0249 (12)	−0.0073 (11)	0.0057 (12)	0.0031 (9)
C6	0.0331 (12)	0.0206 (10)	0.0241 (11)	−0.0013 (9)	0.0056 (9)	0.0011 (8)
C7	0.0333 (12)	0.0205 (9)	0.0295 (12)	−0.0024 (9)	0.0106 (10)	0.0006 (9)
C8	0.0302 (12)	0.0204 (10)	0.0314 (12)	−0.0019 (9)	0.0075 (10)	−0.0006 (9)
C9	0.078 (2)	0.0311 (13)	0.0308 (13)	−0.0176 (13)	0.0137 (14)	−0.0018 (10)
C10	0.084 (2)	0.0276 (12)	0.0446 (16)	−0.0188 (14)	0.0214 (16)	0.0009 (11)
C11	0.0532 (16)	0.0364 (13)	0.0303 (13)	−0.0066 (12)	0.0010 (12)	−0.0046 (10)
C12	0.0496 (15)	0.0260 (11)	0.0327 (13)	−0.0042 (10)	0.0046 (12)	0.0042 (9)
N1	0.0435 (11)	0.0199 (9)	0.0278 (10)	−0.0049 (8)	0.0077 (9)	0.0005 (7)
N2	0.0487 (13)	0.0241 (9)	0.0258 (10)	−0.0087 (9)	0.0066 (9)	0.0016 (7)
N3	0.0523 (13)	0.0239 (9)	0.0265 (10)	−0.0089 (9)	0.0073 (10)	0.0020 (8)
N4	0.0348 (10)	0.0192 (9)	0.0261 (10)	−0.0021 (7)	0.0078 (8)	0.0005 (7)
N5	0.0488 (13)	0.0280 (10)	0.0458 (13)	−0.0092 (9)	0.0112 (11)	−0.0087 (9)
O1	0.0405 (10)	0.0387 (10)	0.0295 (9)	−0.0055 (8)	0.0120 (8)	−0.0026 (8)
O2	0.0349 (10)	0.0577 (12)	0.0288 (9)	0.0058 (9)	0.0035 (8)	−0.0038 (8)
O3	0.0458 (10)	0.0258 (8)	0.0299 (9)	−0.0037 (7)	0.0060 (8)	−0.0015 (7)

Geometric parameters (Å, º) top

Cd1—N1ⁱ	2.278 (2)	C7—N4	1.353 (3)
Cd1—N1	2.278 (2)	C7—C8	1.467 (3)
Cd1—O2	2.304 (2)	C8—C12	1.379 (3)
Cd1—O2ⁱ	2.304 (2)	C8—C9	1.386 (3)
Cd1—O1ⁱ	2.322 (2)	C9—C10	1.373 (3)
Cd1—O1	2.322 (2)	C9—H9	0.9300
C1—N1	1.334 (3)	C10—N5	1.325 (3)
C1—C2	1.370 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—N5	1.327 (3)
C2—C3	1.385 (3)	C11—C12	1.376 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.385 (3)	C12—H12	0.9300
C3—C6	1.461 (3)	N2—N3	1.362 (3)
C4—C5	1.376 (3)	O1—H1A	0.844 (17)
C4—H4	0.9300	O1—H1B	0.845 (17)
C5—N1	1.331 (3)	O2—H2A	0.857 (17)
C5—H5	0.9300	O2—H2B	0.847 (17)
C6—N2	1.330 (3)	O3—H3A	0.848 (16)
C6—N4	1.352 (3)	O3—H3B	0.850 (17)
C7—N3	1.329 (3)

N1ⁱ—Cd1—N1	180.0	N3—C7—N4	113.8 (2)
N1ⁱ—Cd1—O2	90.47 (7)	N3—C7—C8	121.7 (2)
N1—Cd1—O2	89.53 (7)	N4—C7—C8	124.5 (2)
N1ⁱ—Cd1—O2ⁱ	89.53 (7)	C12—C8—C9	116.6 (2)
N1—Cd1—O2ⁱ	90.47 (7)	C12—C8—C7	122.1 (2)
O2—Cd1—O2ⁱ	180.0	C9—C8—C7	121.3 (2)
N1ⁱ—Cd1—O1ⁱ	91.96 (7)	C10—C9—C8	119.5 (2)
N1—Cd1—O1ⁱ	88.04 (7)	C10—C9—H9	120.3
O2—Cd1—O1ⁱ	86.71 (7)	C8—C9—H9	120.3
O2ⁱ—Cd1—O1ⁱ	93.29 (7)	N5—C10—C9	124.3 (2)
N1ⁱ—Cd1—O1	88.04 (7)	N5—C10—H10	117.8
N1—Cd1—O1	91.96 (7)	C9—C10—H10	117.8
O2—Cd1—O1	93.29 (7)	N5—C11—C12	124.3 (2)
O2ⁱ—Cd1—O1	86.71 (7)	N5—C11—H11	117.9
O1ⁱ—Cd1—O1	180.0	C12—C11—H11	117.9
N1—C1—C2	122.9 (2)	C11—C12—C8	119.6 (2)
N1—C1—H1	118.5	C11—C12—H12	120.2
C2—C1—H1	118.5	C8—C12—H12	120.2
C1—C2—C3	120.4 (2)	C5—N1—C1	117.07 (19)
C1—C2—H2	119.8	C5—N1—Cd1	120.33 (15)
C3—C2—H2	119.8	C1—N1—Cd1	122.54 (15)
C2—C3—C4	116.5 (2)	C6—N2—N3	105.89 (18)
C2—C3—C6	120.91 (19)	C7—N3—N2	105.73 (18)
C4—C3—C6	122.5 (2)	C6—N4—C7	100.94 (18)
C5—C4—C3	119.6 (2)	C10—N5—C11	115.8 (2)
C5—C4—H4	120.2	Cd1—O1—H1A	111 (2)
C3—C4—H4	120.2	Cd1—O1—H1B	117 (2)
N1—C5—C4	123.5 (2)	H1A—O1—H1B	108 (2)
N1—C5—H5	118.3	Cd1—O2—H2A	117 (2)
C4—C5—H5	118.3	Cd1—O2—H2B	128 (2)
N2—C6—N4	113.65 (19)	H2A—O2—H2B	108 (2)
N2—C6—C3	121.01 (19)	H3A—O3—H3B	108 (2)
N4—C6—C3	125.27 (19)

N1—C1—C2—C3	0.6 (4)	C2—C1—N1—C5	1.3 (4)
C1—C2—C3—C4	−2.3 (4)	C2—C1—N1—Cd1	178.6 (2)
C1—C2—C3—C6	175.5 (2)	O2—Cd1—N1—C5	−38.2 (2)
C2—C3—C4—C5	2.2 (4)	O2ⁱ—Cd1—N1—C5	141.8 (2)
C6—C3—C4—C5	−175.5 (2)	O1ⁱ—Cd1—N1—C5	48.5 (2)
C3—C4—C5—N1	−0.4 (4)	O1—Cd1—N1—C5	−131.5 (2)
C2—C3—C6—N2	4.4 (3)	O2—Cd1—N1—C1	144.6 (2)
C4—C3—C6—N2	−178.0 (2)	O2ⁱ—Cd1—N1—C1	−35.4 (2)
C2—C3—C6—N4	−172.4 (2)	O1ⁱ—Cd1—N1—C1	−128.6 (2)
C4—C3—C6—N4	5.2 (4)	O1—Cd1—N1—C1	51.4 (2)
N3—C7—C8—C12	171.4 (2)	N4—C6—N2—N3	0.9 (3)
N4—C7—C8—C12	−6.7 (4)	C3—C6—N2—N3	−176.3 (2)
N3—C7—C8—C9	−5.4 (4)	N4—C7—N3—N2	0.3 (3)
N4—C7—C8—C9	176.4 (2)	C8—C7—N3—N2	−178.0 (2)
C12—C8—C9—C10	0.0 (4)	C6—N2—N3—C7	−0.6 (3)
C7—C8—C9—C10	177.0 (3)	N2—C6—N4—C7	−0.7 (3)
C8—C9—C10—N5	0.4 (5)	C3—C6—N4—C7	176.3 (2)
N5—C11—C12—C8	0.6 (4)	N3—C7—N4—C6	0.2 (3)
C9—C8—C12—C11	−0.4 (4)	C8—C7—N4—C6	178.5 (2)
C7—C8—C12—C11	−177.5 (2)	C9—C10—N5—C11	−0.3 (5)
C4—C5—N1—C1	−1.4 (4)	C12—C11—N5—C10	−0.2 (4)
C4—C5—N1—Cd1	−178.7 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱⁱ	0.84 (2)	1.95 (3)	2.768 (3)	164 (3)
O1—H1B···O3	0.85 (3)	1.95 (3)	2.786 (3)	169 (3)
O2—H2A···N3ⁱⁱⁱ	0.85 (3)	1.98 (3)	2.829 (3)	171 (3)
O2—H2B···O3^iv	0.85 (3)	1.95 (3)	2.758 (3)	161 (3)
O3—H3A···N4^v	0.85 (3)	2.06 (2)	2.895 (3)	171 (3)
O3—H3B···N5^vi	0.85 (3)	1.95 (2)	2.796 (3)	170 (3)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₂H₈N₅)₂(H₂O)₄]·2H₂O
M_r	664.97
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5030 (15), 15.748 (3), 12.009 (2)
β (°)	106.68 (3)
V (Å³)	1359.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.40 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.815, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	9599, 3101, 2663
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.070, 1.01
No. of reflections	3101
No. of parameters	211
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.47

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
O1—H1A···N2ⁱ	0.84 (2)	1.95 (3)	2.768 (3)	164 (3)
O1—H1B···O3	0.85 (3)	1.95 (3)	2.786 (3)	169 (3)
O2—H2A···N3ⁱⁱ	0.85 (3)	1.98 (3)	2.829 (3)	171 (3)
O2—H2B···O3ⁱⁱⁱ	0.85 (3)	1.95 (3)	2.758 (3)	161 (3)
O3—H3A···N4^iv	0.85 (3)	2.06 (2)	2.895 (3)	171 (3)
O3—H3B···N5^v	0.85 (3)	1.95 (2)	2.796 (3)	170 (3)

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

Acknowledgements

We gratefully acknowledge the Science and Techology Foundation of Shaoyang, Hunan, China and the Foundation of Shaoyang Medical College, China.

References

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