Tetra­aqua­bis{5-[2-(1H-tetrazol-5-yl)ethenyl]pyrazolato-κN2}manganese(II) dihydrate

Hu, T.

doi:10.1107/S1600536808012464

metal-organic compounds

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Volume 64| Part 6| June 2008| Page m772

doi:10.1107/S1600536808012464

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Tetraaquabis{5-[2-(1H-tetrazol-5-yl)ethenyl]pyrazolato-κN²}manganese(II) dihydrate

Tuoping Hu ^a ^*

^aDepartment of Chemistry, North University of China, Taiyuan, Shanxi 030051, People's Republic of China
^*Correspondence e-mail: hutuopingsx@yahoo.com.cn

(Received 8 January 2008; accepted 29 April 2008; online 3 May 2008)

The title compound, [Mn(C₄H₃N₈)₂(H₂O)₄]·2H₂O, represents the first structurally characterized transition metal complex of the 1,2-bis(tetrazol-5-yl)ethene ligand. The complex molecule occupies a special position on an inversion centre and the Mn atom has a tetragonally distorted octahedral coordination. The bis(tetrazolyl)ethene ligand is planar within 0.0366 (7) Å. All `active' H atoms participate in hydrogen bonds, which link molecules of the complex and the uncoordinated water molecules into an infinite three-dimensional framework.

Related literature

For related literature, see: Huang et al. (2005 ); Demko & Sharpless (2001 ).

Experimental

Crystal data

[Mn(C₄H₃N₈)₂(H₂O)₄]·2H₂O
M_r = 489.32
Triclinic, $[P \overline 1]$
a = 6.2296 (2) Å
b = 7.0093 (2) Å
c = 12.1212 (3) Å
α = 84.405 (1)°
β = 89.457 (1)°
γ = 67.016 (1)°
V = 484.70 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 273 (2) K
0.36 × 0.28 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.717, T_max = 0.887
9107 measured reflections
3246 independent reflections
3149 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.068
S = 1.04
3246 reflections
179 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O1	2.1923 (7)
Mn1—O2	2.1835 (8)
Mn1—N2	2.2538 (7)

O2—Mn1—O1	84.57 (3)
O2—Mn1—N2	91.07 (3)
O1—Mn1—N2	90.24 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1ⁱ	0.833 (18)	2.021 (18)	2.8419 (10)	168.8 (17)
O1—H1A⋯O3ⁱⁱ	0.823 (18)	1.940 (18)	2.7599 (11)	174.0 (16)
O2—H2B⋯O3ⁱⁱⁱ	0.790 (18)	1.996 (19)	2.7797 (11)	171.4 (18)
O2—H2A⋯N6^iv	0.81 (2)	2.04 (2)	2.8472 (10)	173.7 (18)
O3—H3A⋯N5^v	0.82 (2)	2.09 (2)	2.8922 (11)	164.2 (19)
O3—H3B⋯O1	0.80 (2)	2.30 (2)	3.0693 (12)	160 (2)
N8—H8⋯N4^vi	0.926 (18)	1.792 (18)	2.7171 (10)	176.6 (16)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z+1; (v) -x+1, -y+1, -z; (vi) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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/S1600536808012464/ya2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012464/ya2068Isup2.hkl

checkCIF report

Comment top

The 1,2-bis(1,2,3,4-tetrazol-5-yl)ethene ligand (H₂BTAE) was previously reported in its twice deprotonated form in the cystal structure of its sodium salt pentahydrate (Huang et al., 2005). The present paper provides the fist example of its structurally characterized complex with a transition metal; the ligand in this complex is monodeprotonated.

The molecule of Mn(H-BTAE)₂(H₂O)₄ occupies a special position in the inversion centre (Fig. 1); the Mn1 atom has a tetragonally distorted octahedral coordination (Table 1). The H-BTAE ligand has essentailly planar conformation, the maximum deviation of the N6 atom from its mean plane being 0.0366 (7) Å. The geometry of the ligand is similar to the one observed in Huang et al. (2005).

All "active" hydrogen atoms in the structure participate in the H-bonding (Table 2); the extensive H-bond system links molecules of the complex and non-coordinated water molecules into three-dimensional infinite network (Fig. 2).

Related literature top

For related literature, see: Huang et al. (2005); Demko & Sharpless (2001)

Experimental top

MnCl₂.4H₂O (0.5 mmol, 99 mg) and 1,2-bis(1,2,3,4-tetrazol-5-yl)ethene (1 mmol, 192 mg) (Demko & Sharpless, 2001) were added to 30 ml of water:MeOH (1:1) mixture. After stirring for 30 min at room temperature, the pH value was adjusted to 7 by 1M NaOH, and clear solution was allowed to evaporate in the air. Nice prism-shaped crystals of the title compound were obtained after 3 days. The crystals were filtered, washed by EtOH and dried in the air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (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. Molecular structure showing 50% probability displacement ellipsoids. The unlabeled atoms are derived from the reference atoms by means of the (1 - x, -y, 1 - z) symmetry transformation..
	Fig. 2. Packing diagram viewed down the a axis, The hydrogen bonds are shown as dotted lines.

Tetraaquabis{5-[2-(1H-tetrazol-5-yl)ethenyl]pyrazolato-κN²}manganese(II) dihydrate top

Crystal data top

[Mn(C₄H₃N₈)₂(H₂O)₄]·2H₂O	Z = 1
M_r = 489.32	F(000) = 251
Triclinic, P1	D_x = 1.676 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2296 (2) Å	Cell parameters from 7983 reflections
b = 7.0093 (2) Å	θ = 3.2–33.5°
c = 12.1212 (3) Å	µ = 0.75 mm⁻¹
α = 84.405 (1)°	T = 273 K
β = 89.457 (1)°	Prism, brown
γ = 67.016 (1)°	0.36 × 0.28 × 0.16 mm
V = 484.70 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3246 independent reflections
Radiation source: fine-focus sealed tube	3149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 33.5°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.717, T_max = 0.887	k = −10→10
9107 measured reflections	l = −16→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	All H-atom parameters refined
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.039P)² + 0.093P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3246 reflections	Δρ_max = 0.37 e Å⁻³
179 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Crystal data top

[Mn(C₄H₃N₈)₂(H₂O)₄]·2H₂O	γ = 67.016 (1)°
M_r = 489.32	V = 484.70 (2) Å³
Triclinic, P1	Z = 1
a = 6.2296 (2) Å	Mo Kα radiation
b = 7.0093 (2) Å	µ = 0.75 mm⁻¹
c = 12.1212 (3) Å	T = 273 K
α = 84.405 (1)°	0.36 × 0.28 × 0.16 mm
β = 89.457 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3246 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3149 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.887	R_int = 0.015
9107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.068	All H-atom parameters refined
S = 1.05	Δρ_max = 0.37 e Å⁻³
3246 reflections	Δρ_min = −0.22 e Å⁻³
179 parameters

Special details top

Experimental. H atoms were located on intermediate difference Fourier map

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
Mn1	0.5000	0.0000	0.5000	0.02323 (6)
O1	0.13139 (12)	0.18659 (13)	0.45633 (6)	0.03342 (15)
O2	0.48182 (15)	0.26842 (14)	0.58308 (6)	0.03732 (17)
O3	0.15295 (14)	0.60925 (13)	0.38023 (6)	0.03452 (15)
H3A	0.108 (4)	0.639 (3)	0.3151 (17)	0.063 (5)*
H3B	0.180 (4)	0.488 (3)	0.3935 (17)	0.068 (6)*
N1	0.80858 (13)	0.13919 (13)	0.30839 (6)	0.02546 (14)
N2	0.60467 (13)	0.13162 (13)	0.34123 (6)	0.02647 (14)
N3	0.46087 (14)	0.17201 (14)	0.25572 (6)	0.02953 (16)
N4	0.56698 (13)	0.20725 (13)	0.16459 (6)	0.02663 (15)
N5	1.08450 (14)	0.30165 (13)	−0.16586 (6)	0.02657 (14)
N6	1.28887 (14)	0.30586 (14)	−0.20234 (6)	0.02983 (16)
N7	1.43373 (14)	0.27581 (14)	−0.12043 (6)	0.03067 (16)
N8	1.32424 (13)	0.25048 (12)	−0.02771 (6)	0.02534 (14)
C1	0.78023 (14)	0.18638 (13)	0.19858 (6)	0.02208 (14)
C2	0.96111 (15)	0.20610 (14)	0.12755 (7)	0.02469 (15)
C3	0.93208 (15)	0.24900 (14)	0.01755 (7)	0.02401 (15)
C4	1.11010 (14)	0.26607 (13)	−0.05597 (6)	0.02185 (14)
H3	0.794 (2)	0.271 (2)	−0.0175 (12)	0.035 (3)*
H2	1.104 (3)	0.186 (2)	0.1658 (12)	0.039 (4)*
H8	1.405 (3)	0.232 (3)	0.0389 (15)	0.057 (5)*
H1A	0.047 (3)	0.239 (3)	0.5070 (15)	0.046 (4)*
H1B	0.050 (3)	0.155 (3)	0.4134 (15)	0.055 (5)*
H2B	0.587 (3)	0.304 (3)	0.5865 (15)	0.052 (4)*
H2A	0.417 (3)	0.280 (3)	0.6422 (17)	0.057 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02135 (10)	0.03467 (10)	0.01477 (8)	−0.01276 (7)	0.00178 (6)	−0.00004 (6)
O1	0.0225 (3)	0.0535 (4)	0.0236 (3)	−0.0133 (3)	−0.0009 (2)	−0.0078 (3)
O2	0.0443 (4)	0.0551 (5)	0.0264 (3)	−0.0324 (4)	0.0122 (3)	−0.0141 (3)
O3	0.0370 (4)	0.0392 (4)	0.0279 (3)	−0.0154 (3)	−0.0016 (3)	−0.0036 (3)
N1	0.0241 (3)	0.0396 (4)	0.0164 (3)	−0.0169 (3)	0.0007 (2)	−0.0007 (2)
N2	0.0249 (3)	0.0414 (4)	0.0161 (3)	−0.0170 (3)	0.0019 (2)	0.0003 (3)
N3	0.0255 (3)	0.0484 (4)	0.0179 (3)	−0.0190 (3)	0.0011 (2)	0.0012 (3)
N4	0.0250 (3)	0.0419 (4)	0.0161 (3)	−0.0174 (3)	0.0002 (2)	0.0011 (3)
N5	0.0283 (3)	0.0380 (4)	0.0167 (3)	−0.0167 (3)	0.0015 (2)	−0.0020 (3)
N6	0.0302 (4)	0.0437 (4)	0.0185 (3)	−0.0178 (3)	0.0051 (3)	−0.0027 (3)
N7	0.0268 (4)	0.0464 (4)	0.0213 (3)	−0.0174 (3)	0.0052 (3)	−0.0024 (3)
N8	0.0230 (3)	0.0373 (4)	0.0172 (3)	−0.0138 (3)	0.0015 (2)	−0.0006 (3)
C1	0.0232 (3)	0.0296 (3)	0.0159 (3)	−0.0133 (3)	0.0014 (2)	−0.0012 (2)
C2	0.0236 (4)	0.0351 (4)	0.0190 (3)	−0.0158 (3)	0.0024 (3)	−0.0014 (3)
C3	0.0234 (4)	0.0332 (4)	0.0189 (3)	−0.0150 (3)	0.0025 (3)	−0.0019 (3)
C4	0.0234 (3)	0.0277 (3)	0.0164 (3)	−0.0122 (3)	0.0017 (2)	−0.0021 (2)

Geometric parameters (Å, º) top

Mn1—O2ⁱ	2.1835 (8)	N2—N3	1.3112 (10)
Mn1—O1	2.1923 (7)	N3—N4	1.3336 (9)
Mn1—O2	2.1835 (8)	N4—C1	1.3427 (11)
Mn1—O1ⁱ	2.1923 (7)	N5—C4	1.3304 (10)
Mn1—N2ⁱ	2.2538 (7)	N5—N6	1.3541 (10)
Mn1—N2	2.2538 (7)	N6—N7	1.2931 (11)
O1—H1A	0.823 (18)	N7—N8	1.3420 (10)
O1—H1B	0.833 (18)	N8—C4	1.3403 (11)
O2—H2B	0.790 (18)	N8—H8	0.926 (18)
O2—H2A	0.81 (2)	C1—C2	1.4526 (11)
O3—H3A	0.82 (2)	C2—C3	1.3360 (11)
O3—H3B	0.80 (2)	C2—H2	0.963 (15)
N1—C1	1.3361 (10)	C3—C4	1.4499 (11)
N1—N2	1.3468 (10)	C3—H3	0.914 (14)

O2ⁱ—Mn1—O2	180.0	N3—N2—N1	110.34 (6)
O2ⁱ—Mn1—O1	95.43 (3)	N3—N2—Mn1	115.77 (5)
O2—Mn1—O1	84.57 (3)	N1—N2—Mn1	132.31 (6)
O2ⁱ—Mn1—O1ⁱ	84.57 (3)	N2—N3—N4	108.57 (7)
O2—Mn1—O1ⁱ	95.43 (3)	N3—N4—C1	105.93 (7)
O1—Mn1—O1ⁱ	180.0	C4—N5—N6	105.63 (7)
O2ⁱ—Mn1—N2ⁱ	91.07 (3)	N7—N6—N5	111.07 (7)
O2—Mn1—N2ⁱ	88.93 (3)	N6—N7—N8	106.55 (7)
O1—Mn1—N2ⁱ	89.76 (3)	C4—N8—N7	108.63 (7)
O1ⁱ—Mn1—N2ⁱ	90.24 (3)	C4—N8—H8	134.5 (11)
O2ⁱ—Mn1—N2	88.93 (3)	N7—N8—H8	116.8 (11)
O2—Mn1—N2	91.07 (3)	N1—C1—N4	110.73 (7)
O1—Mn1—N2	90.24 (3)	N1—C1—C2	123.47 (7)
O1ⁱ—Mn1—N2	89.76 (3)	N4—C1—C2	125.79 (7)
N2ⁱ—Mn1—N2	179.999 (2)	C3—C2—C1	122.84 (8)
Mn1—O1—H1A	116.9 (11)	C3—C2—H2	122.3 (9)
Mn1—O1—H1B	125.3 (12)	C1—C2—H2	114.9 (9)
H1A—O1—H1B	106.3 (16)	C2—C3—C4	124.29 (8)
Mn1—O2—H2B	123.3 (13)	C2—C3—H3	121.3 (9)
Mn1—O2—H2A	114.9 (13)	C4—C3—H3	114.4 (9)
H2B—O2—H2A	109.2 (17)	N5—C4—N8	108.11 (7)
H3A—O3—H3B	105.6 (18)	N5—C4—C3	124.43 (8)
C1—N1—N2	104.43 (7)	N8—C4—C3	127.46 (7)

C1—N1—N2—N3	0.04 (10)	N6—N7—N8—C4	−0.01 (10)
C1—N1—N2—Mn1	164.68 (7)	N2—N1—C1—N4	−0.02 (10)
O2ⁱ—Mn1—N2—N3	61.58 (7)	N2—N1—C1—C2	−178.57 (8)
O2—Mn1—N2—N3	−118.42 (7)	N3—N4—C1—N1	−0.01 (10)
O1—Mn1—N2—N3	−33.84 (7)	N3—N4—C1—C2	178.50 (8)
O1ⁱ—Mn1—N2—N3	146.16 (7)	N1—C1—C2—C3	178.52 (9)
O2ⁱ—Mn1—N2—N1	−102.42 (8)	N4—C1—C2—C3	0.19 (14)
O2—Mn1—N2—N1	77.58 (8)	C1—C2—C3—C4	−178.84 (8)
O1—Mn1—N2—N1	162.16 (8)	N6—N5—C4—N8	0.29 (10)
O1ⁱ—Mn1—N2—N1	−17.84 (8)	N6—N5—C4—C3	−179.93 (8)
N1—N2—N3—N4	−0.05 (11)	N7—N8—C4—N5	−0.18 (10)
Mn1—N2—N3—N4	−167.49 (6)	N7—N8—C4—C3	−179.96 (8)
N2—N3—N4—C1	0.03 (10)	C2—C3—C4—N5	177.57 (9)
C4—N5—N6—N7	−0.30 (10)	C2—C3—C4—N8	−2.68 (15)
N5—N6—N7—N8	0.19 (11)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1ⁱⁱ	0.833 (18)	2.021 (18)	2.8419 (10)	168.8 (17)
O1—H1A···O3ⁱⁱⁱ	0.823 (18)	1.940 (18)	2.7599 (11)	174.0 (16)
O2—H2B···O3^iv	0.790 (18)	1.996 (19)	2.7797 (11)	171.4 (18)
O2—H2A···N6^v	0.81 (2)	2.04 (2)	2.8472 (10)	173.7 (18)
O3—H3A···N5^vi	0.82 (2)	2.09 (2)	2.8922 (11)	164.2 (19)
O3—H3B···O1	0.80 (2)	2.30 (2)	3.0693 (12)	160 (2)
N8—H8···N4^vii	0.926 (18)	1.792 (18)	2.7171 (10)	176.6 (16)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₄H₃N₈)₂(H₂O)₄]·2H₂O
M_r	489.32
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	6.2296 (2), 7.0093 (2), 12.1212 (3)
α, β, γ (°)	84.405 (1), 89.457 (1), 67.016 (1)
V (Å³)	484.70 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.36 × 0.28 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.717, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	9107, 3246, 3149
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.777

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.068, 1.05
No. of reflections	3246
No. of parameters	179
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.22

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—O1	2.1923 (7)	O3—H3A	0.82 (2)
Mn1—O2	2.1835 (8)	O3—H3B	0.80 (2)
Mn1—N2	2.2538 (7)

O2—Mn1—O1	84.57 (3)	O1—Mn1—N2	90.24 (3)
O2—Mn1—N2	91.07 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1ⁱ	0.833 (18)	2.021 (18)	2.8419 (10)	168.8 (17)
O1—H1A···O3ⁱⁱ	0.823 (18)	1.940 (18)	2.7599 (11)	174.0 (16)
O2—H2B···O3ⁱⁱⁱ	0.790 (18)	1.996 (19)	2.7797 (11)	171.4 (18)
O2—H2A···N6^iv	0.81 (2)	2.04 (2)	2.8472 (10)	173.7 (18)
O3—H3A···N5^v	0.82 (2)	2.09 (2)	2.8922 (11)	164.2 (19)
O3—H3B···O1	0.80 (2)	2.30 (2)	3.0693 (12)	160 (2)
N8—H8···N4^vi	0.926 (18)	1.792 (18)	2.7171 (10)	176.6 (16)

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

Acknowledgements

The author is grateful for funding from the Natural Science Foundation of Shanxi Province (2007011033), the Program of Technological Industrialization in Universities of Shanxi Province (20070308) and the Start-up Fund of the Northern University of China.

References

Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Demko, Z. P. & Sharpless, K. B. (2001). J. Org. Chem. 66, 7945–7950. Web of Science CrossRef PubMed CAS Google Scholar
Huang, X. F., Song, Y. M., Wu, Q., Ye, Q., Chen, X. B., Xiong, R. G. & You, X. Z. (2005). Inorg. Chem. Commun. 8, 58–60. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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