Diazido­bis[4,4,5,5-tetra­methyl-2-(1,3-thia­zol-2-yl)-2-imidazoline-1-oxyl-3-oxide-κ2O,N]manganese(II)

Chang, J.L.; Gao, Z.Y.; Jiang, K.

doi:10.1107/S1600536809000786

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m181

doi:10.1107/S1600536809000786

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Diazidobis[4,4,5,5-tetramethyl-2-(1,3-thiazol-2-yl)-2-imidazoline-1-oxyl-3-oxide-κ²O,N]manganese(II)

Jiu Li Chang,^a Zhi Yong Gao ^a and Kai Jiang ^a ^*

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453002, People's Republic of China
^*Correspondence e-mail: gaozhy201@sohu.com

(Received 25 December 2008; accepted 7 January 2009; online 14 January 2009)

In the crystal structure of the title compound, [Mn(N₃)₂(C₁₀H₁₄N₃O₂S)₂], the Mn(II) atom exhibits a roughly octahedral coordination geometry. The Mn(II) atom lies on an inversion centre, thus the asymmetric unit comprises one half-molecule. The metal center is six-coordinated by two azide anions and by two chelating 4,4,5,5-tetramethyl-2-(1,3-thiazol-2-yl)-2-imidazoline-1-oxyl-3-oxide nitronyl nitroxide radical ligands, leading to two six-membered chelate rings.

Related literature

For the design and synthesis of molecule-based magnetic materials, see: Aoki et al. (2003 ). For nitronyl nitroxide radicals, see: Minguet et al. (2000 ); Catala et al. (2005 ). For transition metal–radical complexes, see: Wang et al. (2005 ). For paramagnetic metal complexes of nitronyl nitroxide radicals, see: Li et al. (2002 ); Liu et al. (2001 ). For the synthesis, see: Ullman et al. (1970 , 1972 )

Experimental

Crystal data

[Mn(N₃)₂(C₁₀H₁₄N₃O₂S)₂]
M_r = 619.60
Monoclinic, P 2₁ /c
a = 9.9600 (18) Å
b = 12.272 (2) Å
c = 11.353 (2) Å
β = 103.714 (3)°
V = 1348.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 291 (2) K
0.45 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.745, T_max = 0.846
7966 measured reflections
3061 independent reflections
2628 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.06
3061 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000786/kp2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000786/kp2202Isup2.hkl

checkCIF report

Comment top

The design and synthesis of molecule-based magnetic materials is one of the major subjects of materials science(Aoki et al. 2003). In many different types of organic radicals, research has focused on the nitronyl nitroxide radicals (NITR) family because of their flexibility and functionality (Minguet et al. 2000; Catala et al. 2005). The nitroxide derivatives can be bound to the metal center through the oxygen atoms of O–N groups, affording a good variety of transition metal–radical complexes (Wang et al. 2005;). There have been many magnetic studies on transition metal complexes with nitronyl nitroxide and imino nitroxide radicals and paramagnetic metal complexes of nitronyl nitroxide radicals have been extensively studied (Li et al. 2002; Liu et al. 2001). In the present paper, we report the synthesis and crystal structure of the title compound Mn(N₃)₂(NIT2-thz)₂.

Related literature top

For the design and synthesis of molecule-based magnetic materials, see: Aoki et al. 2003. For nitronyl nitroxide radicals, see: Minguet et al. (2000); Catala et al. (2005). For transition metal–radical complexes, see: Wang et al. (2005). For paramagnetic metal complexes of nitronyl nitroxide radicals, see: Li et al. (2002); Liu et al. (2001). For the synthesis of the title compound see: Ullman et al. (1970, 1972)

Experimental top

NIT2-thz [NIT2-thz = 4,4,5,5-tetramethyl-2-(1,3-thiazol-2-yl)-2-imidazoline-1-oxyl-3-oxide] was synthesized using a method in the literatrue (Ullman et al. 1970; Ullman et al. 1972). Mn (Ac)₂. 4H₂O(1 mmol) and NIT2-thz (2 mmol) were mixed in 30 ml of methanol. An aqueous solution (10 ml) of NaN₃ (2 mmol) was added to this solution. The mixture was stirred for an 1 h and filtered off. The filtrate was kept at room temperatrue for 1 meek, and well formed dark brown crstals of Mn(N₃)₂(NIT2-thz)₂ were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: publCIF (Westrip, 2009).

Figures top

Fig. 1. ORTEP drawing of the title compound with atom labeling. The thermal ellipsoids are drawn at 30% probability level.[symmetry codes: x,-y,-z + 1].

Diazidobis[4,4,5,5-tetramethyl-2-(1,3-thiazol-2-yl)-2-imidazoline-1-oxyl- 3-oxide-κ²O,N]manganese(II) top

Crystal data top

[Mn(N₃)₂(C₁₀H₁₄N₃O₂S)₂]	F(000) = 642
M_r = 619.60	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4318 reflections
a = 9.9600 (18) Å	θ = 2.5–28.2°
b = 12.272 (2) Å	µ = 0.70 mm⁻¹
c = 11.353 (2) Å	T = 291 K
β = 103.714 (3)°	Block, dark brown
V = 1348.1 (4) Å³	0.45 × 0.30 × 0.25 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3061 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.745, T_max = 0.846	k = −15→15
7966 measured reflections	l = −12→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0605P)² + 0.2559P] where P = (F_o² + 2F_c²)/3
3061 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Mn(N₃)₂(C₁₀H₁₄N₃O₂S)₂]	V = 1348.1 (4) Å³
M_r = 619.60	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9600 (18) Å	µ = 0.70 mm⁻¹
b = 12.272 (2) Å	T = 291 K
c = 11.353 (2) Å	0.45 × 0.30 × 0.25 mm
β = 103.714 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3061 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2628 reflections with I > 2σ(I)
T_min = 0.745, T_max = 0.846	R_int = 0.036
7966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	Δρ_max = 0.37 e Å⁻³
3061 reflections	Δρ_min = −0.25 e Å⁻³
182 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
Mn1	0.0000	0.0000	0.5000	0.03345 (14)
S1	0.25159 (5)	0.27889 (4)	0.36683 (5)	0.05049 (17)
O1	0.17034 (15)	−0.08711 (11)	0.44955 (14)	0.0504 (4)
O2	0.38630 (18)	0.14599 (13)	0.23568 (17)	0.0660 (5)
N1	0.12384 (15)	0.14413 (11)	0.47278 (13)	0.0337 (3)
N2	0.23912 (14)	−0.05108 (11)	0.37542 (13)	0.0336 (3)
N3	0.34509 (15)	0.05765 (13)	0.27421 (14)	0.0407 (4)
N4	−0.1080 (2)	0.00819 (18)	0.31193 (18)	0.0641 (6)
N5	−0.08511 (17)	0.04681 (12)	0.22465 (15)	0.0433 (4)
N6	−0.0640 (3)	0.08223 (18)	0.13715 (19)	0.0761 (7)
C1	0.1569 (2)	0.32772 (15)	0.4616 (2)	0.0495 (5)
H1	0.1479	0.4012	0.4782	0.059*
C2	0.0969 (2)	0.24624 (14)	0.50955 (17)	0.0412 (4)
H2	0.0413	0.2584	0.5635	0.049*
C3	0.20718 (16)	0.14870 (12)	0.39806 (15)	0.0318 (3)
C4	0.25886 (16)	0.05337 (13)	0.34979 (15)	0.0317 (3)
C5	0.40415 (19)	−0.05207 (16)	0.25646 (16)	0.0406 (4)
C6	0.30045 (18)	−0.12873 (14)	0.29998 (16)	0.0382 (4)
C7	0.4089 (3)	−0.0651 (2)	0.12397 (19)	0.0628 (6)
H7A	0.3179	−0.0551	0.0732	0.094*
H7B	0.4417	−0.1367	0.1114	0.094*
H7C	0.4702	−0.0116	0.1039	0.094*
C8	0.5497 (2)	−0.0545 (2)	0.3366 (2)	0.0601 (6)
H8A	0.6029	0.0037	0.3137	0.090*
H8B	0.5923	−0.1230	0.3269	0.090*
H8C	0.5461	−0.0455	0.4197	0.090*
C9	0.1798 (2)	−0.1673 (2)	0.1994 (2)	0.0595 (6)
H9A	0.1102	−0.1990	0.2346	0.089*
H9B	0.2118	−0.2208	0.1507	0.089*
H9C	0.1413	−0.1064	0.1496	0.089*
C10	0.3643 (3)	−0.22455 (19)	0.3780 (2)	0.0620 (6)
H10A	0.4243	−0.1981	0.4515	0.093*
H10B	0.4167	−0.2680	0.3345	0.093*
H10C	0.2925	−0.2682	0.3974	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0362 (2)	0.0333 (2)	0.0373 (2)	−0.00148 (13)	0.02166 (16)	0.00206 (13)
S1	0.0483 (3)	0.0342 (2)	0.0743 (4)	−0.00716 (19)	0.0251 (3)	0.0074 (2)
O1	0.0597 (9)	0.0351 (6)	0.0717 (10)	0.0065 (6)	0.0459 (8)	0.0095 (6)
O2	0.0697 (10)	0.0592 (9)	0.0861 (12)	−0.0037 (8)	0.0525 (10)	0.0169 (8)
N1	0.0365 (7)	0.0299 (7)	0.0381 (7)	0.0019 (5)	0.0156 (6)	−0.0003 (5)
N2	0.0325 (7)	0.0336 (7)	0.0395 (8)	0.0037 (5)	0.0182 (6)	0.0003 (6)
N3	0.0371 (8)	0.0466 (8)	0.0452 (8)	0.0000 (6)	0.0230 (7)	0.0038 (7)
N4	0.0681 (13)	0.0827 (14)	0.0416 (10)	−0.0251 (10)	0.0134 (9)	0.0060 (9)
N5	0.0497 (9)	0.0360 (8)	0.0453 (9)	−0.0042 (6)	0.0138 (7)	0.0000 (7)
N6	0.121 (2)	0.0587 (12)	0.0582 (12)	−0.0128 (12)	0.0400 (13)	0.0104 (10)
C1	0.0490 (11)	0.0305 (8)	0.0668 (13)	0.0003 (8)	0.0093 (10)	−0.0061 (8)
C2	0.0449 (10)	0.0352 (8)	0.0444 (10)	0.0065 (7)	0.0122 (8)	−0.0065 (7)
C3	0.0297 (8)	0.0302 (7)	0.0372 (8)	−0.0012 (6)	0.0113 (6)	0.0028 (6)
C4	0.0277 (8)	0.0361 (8)	0.0335 (8)	0.0006 (6)	0.0118 (6)	0.0029 (6)
C5	0.0346 (9)	0.0556 (11)	0.0361 (9)	0.0076 (7)	0.0170 (7)	−0.0030 (8)
C6	0.0369 (9)	0.0404 (9)	0.0402 (9)	0.0095 (7)	0.0151 (7)	−0.0048 (7)
C7	0.0640 (14)	0.0898 (17)	0.0422 (11)	0.0087 (12)	0.0277 (10)	−0.0064 (11)
C8	0.0358 (10)	0.0856 (16)	0.0599 (13)	0.0054 (10)	0.0133 (10)	−0.0127 (12)
C9	0.0569 (13)	0.0618 (13)	0.0587 (13)	−0.0084 (10)	0.0117 (11)	−0.0173 (10)
C10	0.0695 (15)	0.0542 (12)	0.0703 (15)	0.0292 (11)	0.0324 (13)	0.0111 (11)

Geometric parameters (Å, º) top

Mn1—N4ⁱ	2.153 (2)	C2—H2	0.9300
Mn1—N4	2.153 (2)	C3—C4	1.438 (2)
Mn1—O1ⁱ	2.1931 (12)	C5—C8	1.518 (3)
Mn1—O1	2.1931 (12)	C5—C7	1.525 (3)
Mn1—N1	2.2194 (14)	C5—C6	1.561 (3)
Mn1—N1ⁱ	2.2194 (14)	C6—C10	1.518 (3)
S1—C1	1.699 (2)	C6—C9	1.524 (3)
S1—C3	1.7170 (16)	C7—H7A	0.9600
O1—N2	1.2832 (17)	C7—H7B	0.9600
O2—N3	1.273 (2)	C7—H7C	0.9600
N1—C3	1.321 (2)	C8—H8A	0.9600
N1—C2	1.367 (2)	C8—H8B	0.9600
N2—C4	1.339 (2)	C8—H8C	0.9600
N2—C6	1.504 (2)	C9—H9A	0.9600
N3—C4	1.3513 (19)	C9—H9B	0.9600
N3—C5	1.502 (2)	C9—H9C	0.9600
N4—N5	1.168 (2)	C10—H10A	0.9600
N5—N6	1.148 (2)	C10—H10B	0.9600
C1—C2	1.345 (3)	C10—H10C	0.9600
C1—H1	0.9300

N4ⁱ—Mn1—N4	180.0	N2—C4—C3	127.70 (14)
N4ⁱ—Mn1—O1ⁱ	89.95 (8)	N3—C4—C3	123.31 (15)
N4—Mn1—O1ⁱ	90.05 (8)	N3—C5—C8	106.60 (17)
N4ⁱ—Mn1—O1	90.05 (8)	N3—C5—C7	109.34 (17)
N4—Mn1—O1	89.95 (8)	C8—C5—C7	109.88 (17)
O1ⁱ—Mn1—O1	180.0	N3—C5—C6	100.84 (13)
N4ⁱ—Mn1—N1	90.68 (6)	C8—C5—C6	114.10 (17)
N4—Mn1—N1	89.32 (6)	C7—C5—C6	115.27 (18)
O1ⁱ—Mn1—N1	97.92 (5)	N2—C6—C10	109.20 (15)
O1—Mn1—N1	82.08 (5)	N2—C6—C9	105.59 (15)
N4ⁱ—Mn1—N1ⁱ	89.32 (6)	C10—C6—C9	110.10 (19)
N4—Mn1—N1ⁱ	90.68 (6)	N2—C6—C5	100.77 (13)
O1ⁱ—Mn1—N1ⁱ	82.08 (5)	C10—C6—C5	115.73 (16)
O1—Mn1—N1ⁱ	97.92 (5)	C9—C6—C5	114.43 (16)
N1—Mn1—N1ⁱ	180.0	C5—C7—H7A	109.5
C1—S1—C3	89.35 (9)	C5—C7—H7B	109.5
N2—O1—Mn1	124.73 (10)	H7A—C7—H7B	109.5
C3—N1—C2	110.83 (14)	C5—C7—H7C	109.5
C3—N1—Mn1	125.29 (11)	H7A—C7—H7C	109.5
C2—N1—Mn1	122.15 (11)	H7B—C7—H7C	109.5
O1—N2—C4	126.95 (13)	C5—C8—H8A	109.5
O1—N2—C6	120.47 (13)	C5—C8—H8B	109.5
C4—N2—C6	112.47 (13)	H8A—C8—H8B	109.5
O2—N3—C4	123.82 (15)	C5—C8—H8C	109.5
O2—N3—C5	123.29 (14)	H8A—C8—H8C	109.5
C4—N3—C5	112.24 (14)	H8B—C8—H8C	109.5
N5—N4—Mn1	135.07 (17)	C6—C9—H9A	109.5
N6—N5—N4	178.1 (2)	C6—C9—H9B	109.5
C2—C1—S1	111.16 (14)	H9A—C9—H9B	109.5
C2—C1—H1	124.4	C6—C9—H9C	109.5
S1—C1—H1	124.4	H9A—C9—H9C	109.5
C1—C2—N1	114.81 (16)	H9B—C9—H9C	109.5
C1—C2—H2	122.6	C6—C10—H10A	109.5
N1—C2—H2	122.6	C6—C10—H10B	109.5
N1—C3—C4	123.11 (14)	H10A—C10—H10B	109.5
N1—C3—S1	113.83 (12)	C6—C10—H10C	109.5
C4—C3—S1	123.04 (12)	H10A—C10—H10C	109.5
N2—C4—N3	108.87 (14)	H10B—C10—H10C	109.5

N4ⁱ—Mn1—O1—N2	−122.97 (15)	O1—N2—C4—N3	175.59 (17)
N4—Mn1—O1—N2	57.03 (15)	C6—N2—C4—N3	−8.19 (19)
O1ⁱ—Mn1—O1—N2	105 (8)	O1—N2—C4—C3	−0.6 (3)
N1—Mn1—O1—N2	−32.28 (14)	C6—N2—C4—C3	175.65 (17)
N1ⁱ—Mn1—O1—N2	147.72 (14)	O2—N3—C4—N2	−178.27 (17)
N4ⁱ—Mn1—N1—C3	118.52 (15)	C5—N3—C4—N2	−7.24 (19)
N4—Mn1—N1—C3	−61.48 (15)	O2—N3—C4—C3	−1.9 (3)
O1ⁱ—Mn1—N1—C3	−151.43 (14)	C5—N3—C4—C3	169.12 (16)
O1—Mn1—N1—C3	28.57 (14)	N1—C3—C4—N2	−3.7 (3)
N1ⁱ—Mn1—N1—C3	24.5 (17)	S1—C3—C4—N2	174.59 (14)
N4ⁱ—Mn1—N1—C2	−77.84 (15)	N1—C3—C4—N3	−179.39 (16)
N4—Mn1—N1—C2	102.16 (15)	S1—C3—C4—N3	−1.1 (2)
O1ⁱ—Mn1—N1—C2	12.20 (15)	O2—N3—C5—C8	70.0 (2)
O1—Mn1—N1—C2	−167.80 (15)	C4—N3—C5—C8	−101.13 (18)
N1ⁱ—Mn1—N1—C2	−171.9 (18)	O2—N3—C5—C7	−48.8 (2)
Mn1—O1—N2—C4	26.1 (2)	C4—N3—C5—C7	140.13 (18)
Mn1—O1—N2—C6	−149.81 (13)	O2—N3—C5—C6	−170.64 (18)
N4ⁱ—Mn1—N4—N5	−71 (2)	C4—N3—C5—C6	18.27 (18)
O1ⁱ—Mn1—N4—N5	118.9 (3)	O1—N2—C6—C10	−42.4 (2)
O1—Mn1—N4—N5	−61.1 (3)	C4—N2—C6—C10	141.14 (17)
N1—Mn1—N4—N5	21.0 (3)	O1—N2—C6—C9	76.0 (2)
N1ⁱ—Mn1—N4—N5	−159.0 (3)	C4—N2—C6—C9	−100.50 (18)
Mn1—N4—N5—N6	137 (8)	O1—N2—C6—C5	−164.65 (15)
C3—S1—C1—C2	−0.76 (16)	C4—N2—C6—C5	18.85 (18)
S1—C1—C2—N1	−0.1 (2)	N3—C5—C6—N2	−20.40 (16)
C3—N1—C2—C1	1.2 (2)	C8—C5—C6—N2	93.45 (18)
Mn1—N1—C2—C1	−164.58 (14)	C7—C5—C6—N2	−138.01 (17)
C2—N1—C3—C4	176.71 (16)	N3—C5—C6—C10	−138.01 (17)
Mn1—N1—C3—C4	−18.1 (2)	C8—C5—C6—C10	−24.2 (2)
C2—N1—C3—S1	−1.76 (19)	C7—C5—C6—C10	104.4 (2)
Mn1—N1—C3—S1	163.46 (8)	N3—C5—C6—C9	92.35 (18)
C1—S1—C3—N1	1.47 (15)	C8—C5—C6—C9	−153.79 (17)
C1—S1—C3—C4	−177.00 (16)	C7—C5—C6—C9	−25.3 (2)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(N₃)₂(C₁₀H₁₄N₃O₂S)₂]
M_r	619.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	9.9600 (18), 12.272 (2), 11.353 (2)
β (°)	103.714 (3)
V (Å³)	1348.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.45 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.745, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	7966, 3061, 2628
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.06
No. of reflections	3061
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.25

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20471026) and the Natural Science Foundation of Henan Province (grant No. 0311021200).

References

Aoki, C., Ishida, T. & Nogami, T. (2003). Inorg. Chem. 42, 7616–7625. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA. Google Scholar
Catala, L., Moigne, J. L., Gruber, N., Novoa, J. J., Rabu, P., Belorizky, E. & Turek, P. (2005). Chem. Eur. J. 11, 2440–2454. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, L. C., Liao, D. Z., Jiang, Z. H. & &Yan, S. P. (2002). J. Chem. Soc. Dalton Trans. pp. 1350–1353. Web of Science CSD CrossRef Google Scholar
Liu, Z. L., Zhao, Q. H., Li, S. Q., Liao, D. Z. & Jiang, Z. H. (2001). Inorg. Chem. Commun. 4, 322–325. Web of Science CSD CrossRef CAS Google Scholar
Minguet, M., Amabilino, D. B., Cirujeda, J., Wurst, K., Mata, I., Molins, E., Novoa, J. J. & Veciana, J. (2000). Chem. Eur. J. 6, 2350–2361. CrossRef PubMed 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
Ullman, E. F., Call, L. & Osieckei, J. H. J. (1970). J. Org. Chem. 35, 3623–3628. CrossRef CAS Web of Science Google Scholar
Ullman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1972). J. Am. Chem. Soc. 94, 7049–7059. CrossRef CAS Web of Science Google Scholar
Wang, L.-Y., Chang, J.-L., Jiang, K., Ma, L.-F. & Wang, Y.-F. (2005). Acta Cryst. E61, m2230–m2231. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009) publCIF. In preparation. Google Scholar

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