{N′-[(E)-1-(5-Bromo-2-oxidophen­yl)ethyl­idene]-4-chloro­benzohydrazidato}pyridinenickel(II)

Chang, X.-L.; Xie, B.; Ji, C.-Y.; Xiang, Y.-G.; Zou, L.-K.

doi:10.1107/S160053680902234X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m794

doi:10.1107/S160053680902234X

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{N′-[(E)-1-(5-Bromo-2-oxidophenyl)ethylidene]-4-chlorobenzohydrazidato}pyridinenickel(II)

Xiu-Li Chang,^a ^* Bin Xie,^a Chang-You Ji,^b Yang-Guang Xiang ^a and Li-Ke Zou ^a

^aSchool of Chemistry & Pharmaceutical Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, People's Republic of China, and ^bCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China
^*Correspondence e-mail: changxiuli456789@126.com

(Received 8 May 2009; accepted 11 June 2009; online 20 June 2009)

The title complex, [Ni(C₁₅H₁₀BrClN₂O₂)(C₅H₅N)], displays a square-planar coordination geometry around the Ni^II ion, formed by the tridentate hydrazone and monodentate pyridine ligands, with the N atoms in a trans arrangement about the Ni center.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 ); Carcelli et al. (1995 ); Salem (1998 ); Singh et al. (1982 ).

Experimental

Crystal data

[Ni(C₁₅H₁₀BrClN₂O₂)(C₅H₅N)]
M_r = 503.42
Monoclinic, C 2/c
a = 32.430 (4) Å
b = 6.0816 (8) Å
c = 22.865 (3) Å
β = 121.422 (2)°
V = 3848.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 3.25 mm⁻¹
T = 278 K
0.18 × 0.13 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.581, T_max = 0.723
9680 measured reflections
3401 independent reflections
2651 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.080
S = 1.02
3401 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S160053680902234X/bh2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902234X/bh2230Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998; Ali et al., 2004) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported.

Related literature top

For the coordination properties of aroylhydrazones, see: Ali et al. (2004); Carcelli et al. (1995); Salem (1998); Singh et al. (1982).

Experimental top

A DMF solution (5 ml) of N'-[(E)-(5-bromo-2-hydroxyphenyl)ethylidene]-4-chlorobenzo-hydrazide (0.25 mmol, 0.092 g) was mixed with a methanol solution (5 ml) of NiCl₂.6H₂O (0.25 mmol, 0.059 g). The mixture was stirred at 298 K for 4 h and then filtered. A green precipitate was produced after about 10 d. A pyridine mixture (5 ml) was used to dissolve the precipitate at 330 K. Dark green block-shaped crystals were obtained after one month (yield 30%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.

{N'-[(E)-1-(5-Bromo-2-oxidophenyl)ethylidene]-4- chlorobenzohydrazidato}pyridinenickel(II) top

Crystal data top

[Ni(C₁₅H₁₀BrClNO₂)(C₅H₅N)]	F(000) = 2016
M_r = 503.42	D_x = 1.738 Mg m⁻³
Monoclinic, C2/c	Melting point: 330 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 32.430 (4) Å	Cell parameters from 2958 reflections
b = 6.0816 (8) Å	θ = 2.6–25.0°
c = 22.865 (3) Å	µ = 3.25 mm⁻¹
β = 121.422 (2)°	T = 278 K
V = 3848.3 (9) Å³	Block, green
Z = 8	0.18 × 0.13 × 0.10 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	2651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→38
T_min = 0.581, T_max = 0.723	k = −7→7
9680 measured reflections	l = −24→27

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0383P)² + 2.3403P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³
0 constraints

Crystal data top

[Ni(C₁₅H₁₀BrClNO₂)(C₅H₅N)]	V = 3848.3 (9) Å³
M_r = 503.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.430 (4) Å	µ = 3.25 mm⁻¹
b = 6.0816 (8) Å	T = 278 K
c = 22.865 (3) Å	0.18 × 0.13 × 0.10 mm
β = 121.422 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3401 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2651 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.723	R_int = 0.028
9680 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	Δρ_max = 0.48 e Å⁻³
3401 reflections	Δρ_min = −0.27 e Å⁻³
253 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.041268 (13)	0.23786 (6)	0.156018 (18)	0.04192 (13)
Br1	−0.211124 (13)	−0.09987 (7)	−0.01369 (2)	0.07519 (15)
Cl1	0.26998 (4)	−0.39055 (19)	0.14682 (6)	0.0893 (3)
O1	0.09933 (7)	0.1537 (3)	0.16792 (10)	0.0483 (5)
O2	−0.01644 (7)	0.3235 (3)	0.14192 (11)	0.0532 (5)
N1	0.05323 (9)	−0.1250 (4)	0.09609 (12)	0.0460 (6)
N2	0.01755 (9)	−0.0048 (4)	0.09955 (11)	0.0418 (6)
N3	0.07253 (9)	0.4809 (4)	0.22016 (12)	0.0449 (6)
C1	0.21951 (12)	−0.2894 (6)	0.14580 (16)	0.0572 (9)
C2	0.22207 (12)	−0.0906 (6)	0.17554 (17)	0.0647 (9)
H2	0.2510	−0.0129	0.1980	0.078*
C3	0.18122 (12)	−0.0071 (6)	0.17171 (16)	0.0578 (8)
H3	0.1827	0.1285	0.1915	0.069*
C4	0.13809 (11)	−0.1220 (5)	0.13888 (14)	0.0454 (7)
C5	0.13736 (13)	−0.3249 (5)	0.11103 (18)	0.0595 (9)
H5	0.1089	−0.4065	0.0899	0.071*
C6	0.17748 (13)	−0.4080 (6)	0.11382 (18)	0.0646 (9)
H6	0.1763	−0.5437	0.0942	0.077*
C7	0.09448 (11)	−0.0276 (5)	0.13425 (14)	0.0437 (7)
C8	−0.02649 (11)	−0.0808 (5)	0.06426 (13)	0.0417 (7)
C9	−0.03642 (12)	−0.2861 (5)	0.02193 (16)	0.0539 (8)
H9A	−0.0094	−0.3164	0.0169	0.081*
H9B	−0.0649	−0.2649	−0.0225	0.081*
H9C	−0.0413	−0.4077	0.0444	0.081*
C10	−0.06526 (10)	0.0294 (5)	0.06629 (13)	0.0415 (7)
C11	−0.05843 (11)	0.2266 (5)	0.10261 (15)	0.0456 (7)
C12	−0.09895 (12)	0.3312 (5)	0.09768 (16)	0.0545 (8)
H12	−0.0947	0.4649	0.1198	0.065*
C13	−0.14427 (12)	0.2416 (6)	0.06125 (17)	0.0564 (8)
H13	−0.1706	0.3138	0.0582	0.068*
C14	−0.15003 (11)	0.0428 (6)	0.02932 (15)	0.0516 (8)
C15	−0.11213 (11)	−0.0603 (5)	0.03060 (14)	0.0487 (7)
H15	−0.1174	−0.1926	0.0074	0.058*
C16	0.12054 (12)	0.4904 (6)	0.25973 (16)	0.0600 (9)
H16	0.1387	0.3768	0.2571	0.072*
C17	0.14431 (14)	0.6615 (6)	0.30425 (19)	0.0701 (10)
H17	0.1779	0.6628	0.3311	0.084*
C18	0.11809 (15)	0.8293 (6)	0.30861 (17)	0.0655 (10)
H18	0.1335	0.9482	0.3375	0.079*
C19	0.06898 (14)	0.8192 (5)	0.26974 (17)	0.0589 (9)
H19	0.0503	0.9294	0.2727	0.071*
C20	0.04720 (12)	0.6437 (5)	0.22580 (15)	0.0525 (8)
H20	0.0136	0.6388	0.1992	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0420 (2)	0.0397 (2)	0.0444 (2)	−0.00392 (17)	0.02273 (18)	−0.00596 (17)
Br1	0.0486 (2)	0.0968 (3)	0.0797 (3)	−0.0210 (2)	0.0332 (2)	−0.0084 (2)
Cl1	0.0596 (6)	0.1029 (8)	0.1085 (8)	0.0179 (6)	0.0461 (6)	−0.0134 (6)
O1	0.0456 (12)	0.0462 (12)	0.0522 (12)	−0.0061 (9)	0.0248 (10)	−0.0130 (10)
O2	0.0433 (13)	0.0501 (12)	0.0657 (13)	−0.0055 (10)	0.0281 (11)	−0.0161 (11)
N1	0.0454 (15)	0.0431 (15)	0.0514 (15)	0.0007 (12)	0.0265 (13)	−0.0048 (12)
N2	0.0445 (15)	0.0388 (13)	0.0440 (13)	−0.0011 (11)	0.0245 (12)	−0.0025 (11)
N3	0.0486 (16)	0.0436 (14)	0.0464 (14)	−0.0058 (12)	0.0275 (12)	−0.0051 (11)
C1	0.047 (2)	0.067 (2)	0.058 (2)	0.0122 (17)	0.0272 (17)	0.0007 (17)
C2	0.044 (2)	0.074 (3)	0.074 (2)	−0.0059 (17)	0.0297 (18)	−0.0151 (19)
C3	0.054 (2)	0.057 (2)	0.067 (2)	−0.0062 (17)	0.0347 (18)	−0.0163 (17)
C4	0.0454 (18)	0.0493 (19)	0.0432 (16)	0.0000 (14)	0.0242 (15)	−0.0001 (14)
C5	0.050 (2)	0.054 (2)	0.072 (2)	−0.0075 (16)	0.0299 (18)	−0.0163 (17)
C6	0.065 (2)	0.056 (2)	0.078 (2)	0.0055 (18)	0.040 (2)	−0.0129 (18)
C7	0.0457 (18)	0.0448 (17)	0.0423 (16)	0.0001 (14)	0.0241 (15)	0.0003 (14)
C8	0.0465 (18)	0.0381 (16)	0.0388 (15)	−0.0049 (13)	0.0210 (14)	0.0000 (13)
C9	0.055 (2)	0.0444 (19)	0.0595 (19)	−0.0082 (15)	0.0274 (17)	−0.0105 (15)
C10	0.0414 (17)	0.0421 (17)	0.0425 (15)	−0.0046 (13)	0.0229 (14)	0.0012 (13)
C11	0.0441 (18)	0.0476 (18)	0.0494 (17)	−0.0047 (14)	0.0274 (15)	0.0001 (14)
C12	0.053 (2)	0.0525 (19)	0.064 (2)	−0.0029 (16)	0.0350 (17)	−0.0048 (16)
C13	0.047 (2)	0.066 (2)	0.066 (2)	0.0010 (17)	0.0358 (17)	0.0043 (18)
C14	0.0421 (18)	0.063 (2)	0.0496 (18)	−0.0102 (16)	0.0239 (15)	0.0023 (16)
C15	0.0504 (19)	0.0510 (18)	0.0465 (17)	−0.0095 (15)	0.0266 (15)	−0.0020 (14)
C16	0.048 (2)	0.064 (2)	0.070 (2)	−0.0108 (17)	0.0320 (18)	−0.0193 (18)
C17	0.059 (2)	0.075 (2)	0.074 (2)	−0.025 (2)	0.033 (2)	−0.028 (2)
C18	0.085 (3)	0.059 (2)	0.062 (2)	−0.028 (2)	0.045 (2)	−0.0210 (18)
C19	0.079 (3)	0.0463 (19)	0.059 (2)	−0.0047 (18)	0.042 (2)	−0.0088 (16)
C20	0.056 (2)	0.0511 (19)	0.0510 (18)	−0.0009 (16)	0.0288 (17)	−0.0042 (15)

Geometric parameters (Å, º) top

Ni1—O2	1.802 (2)	C8—C10	1.447 (4)
Ni1—O1	1.830 (2)	C8—C9	1.508 (4)
Ni1—N2	1.844 (2)	C9—H9A	0.9600
Ni1—N3	1.953 (2)	C9—H9B	0.9600
Br1—C14	1.901 (3)	C9—H9C	0.9600
Cl1—C1	1.737 (3)	C10—C15	1.407 (4)
O1—C7	1.306 (3)	C10—C11	1.409 (4)
O2—C11	1.317 (3)	C11—C12	1.410 (4)
N1—C7	1.298 (4)	C12—C13	1.369 (4)
N1—N2	1.405 (3)	C12—H12	0.9300
N2—C8	1.305 (4)	C13—C14	1.374 (4)
N3—C16	1.333 (4)	C13—H13	0.9300
N3—C20	1.335 (4)	C14—C15	1.366 (4)
C1—C2	1.368 (5)	C15—H15	0.9300
C1—C6	1.369 (5)	C16—C17	1.377 (4)
C2—C3	1.378 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.364 (5)
C3—C4	1.383 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.362 (5)
C4—C5	1.383 (4)	C18—H18	0.9300
C4—C7	1.478 (4)	C19—C20	1.381 (4)
C5—C6	1.366 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300

O2—Ni1—O1	178.39 (9)	C8—C9—H9A	109.5
O2—Ni1—N2	95.20 (10)	C8—C9—H9B	109.5
O1—Ni1—N2	84.35 (9)	H9A—C9—H9B	109.5
O2—Ni1—N3	89.99 (10)	C8—C9—H9C	109.5
O1—Ni1—N3	90.52 (9)	H9A—C9—H9C	109.5
N2—Ni1—N3	174.43 (11)	H9B—C9—H9C	109.5
C7—O1—Ni1	110.50 (18)	C15—C10—C11	117.5 (3)
C11—O2—Ni1	126.92 (19)	C15—C10—C8	119.7 (3)
C7—N1—N2	108.4 (2)	C11—C10—C8	122.7 (3)
C8—N2—N1	116.7 (2)	O2—C11—C10	124.9 (3)
C8—N2—Ni1	129.7 (2)	O2—C11—C12	116.2 (3)
N1—N2—Ni1	113.61 (18)	C10—C11—C12	118.9 (3)
C16—N3—C20	117.5 (3)	C13—C12—C11	122.0 (3)
C16—N3—Ni1	120.5 (2)	C13—C12—H12	119.0
C20—N3—Ni1	122.0 (2)	C11—C12—H12	119.0
C2—C1—C6	121.1 (3)	C12—C13—C14	118.6 (3)
C2—C1—Cl1	119.6 (3)	C12—C13—H13	120.7
C6—C1—Cl1	119.3 (3)	C14—C13—H13	120.7
C1—C2—C3	119.1 (3)	C15—C14—C13	121.4 (3)
C1—C2—H2	120.4	C15—C14—Br1	119.0 (3)
C3—C2—H2	120.4	C13—C14—Br1	119.5 (2)
C2—C3—C4	121.0 (3)	C14—C15—C10	121.5 (3)
C2—C3—H3	119.5	C14—C15—H15	119.3
C4—C3—H3	119.5	C10—C15—H15	119.3
C3—C4—C5	118.1 (3)	N3—C16—C17	122.7 (3)
C3—C4—C7	120.1 (3)	N3—C16—H16	118.6
C5—C4—C7	121.8 (3)	C17—C16—H16	118.6
C6—C5—C4	121.4 (3)	C18—C17—C16	119.3 (4)
C6—C5—H5	119.3	C18—C17—H17	120.4
C4—C5—H5	119.3	C16—C17—H17	120.4
C5—C6—C1	119.2 (3)	C19—C18—C17	118.7 (3)
C5—C6—H6	120.4	C19—C18—H18	120.7
C1—C6—H6	120.4	C17—C18—H18	120.7
N1—C7—O1	123.1 (3)	C18—C19—C20	119.4 (3)
N1—C7—C4	118.9 (3)	C18—C19—H19	120.3
O1—C7—C4	118.0 (3)	C20—C19—H19	120.3
N2—C8—C10	120.4 (3)	N3—C20—C19	122.4 (3)
N2—C8—C9	119.3 (3)	N3—C20—H20	118.8
C10—C8—C9	120.4 (3)	C19—C20—H20	118.8

N2—Ni1—O1—C7	−2.06 (18)	N1—N2—C8—C10	178.4 (2)
N3—Ni1—O1—C7	175.76 (18)	Ni1—N2—C8—C10	−0.2 (4)
N2—Ni1—O2—C11	0.0 (2)	N1—N2—C8—C9	−1.0 (4)
N3—Ni1—O2—C11	−178.0 (2)	Ni1—N2—C8—C9	−179.5 (2)
C7—N1—N2—C8	−179.6 (2)	N2—C8—C10—C15	−177.0 (2)
C7—N1—N2—Ni1	−0.8 (3)	C9—C8—C10—C15	2.4 (4)
O2—Ni1—N2—C8	−1.3 (3)	N2—C8—C10—C11	3.4 (4)
O1—Ni1—N2—C8	−179.8 (3)	C9—C8—C10—C11	−177.3 (3)
O2—Ni1—N2—N1	−179.92 (18)	Ni1—O2—C11—C10	2.9 (4)
O1—Ni1—N2—N1	1.62 (17)	Ni1—O2—C11—C12	−177.3 (2)
O2—Ni1—N3—C16	168.9 (2)	C15—C10—C11—O2	175.5 (3)
O1—Ni1—N3—C16	−12.6 (2)	C8—C10—C11—O2	−4.9 (4)
O2—Ni1—N3—C20	−11.7 (2)	C15—C10—C11—C12	−4.3 (4)
O1—Ni1—N3—C20	166.7 (2)	C8—C10—C11—C12	175.4 (3)
C6—C1—C2—C3	−1.5 (5)	O2—C11—C12—C13	−176.7 (3)
Cl1—C1—C2—C3	177.0 (3)	C10—C11—C12—C13	3.1 (5)
C1—C2—C3—C4	0.5 (5)	C11—C12—C13—C14	0.7 (5)
C2—C3—C4—C5	1.1 (5)	C12—C13—C14—C15	−3.2 (5)
C2—C3—C4—C7	−178.9 (3)	C12—C13—C14—Br1	173.6 (2)
C3—C4—C5—C6	−1.9 (5)	C13—C14—C15—C10	1.9 (5)
C7—C4—C5—C6	178.1 (3)	Br1—C14—C15—C10	−175.0 (2)
C4—C5—C6—C1	1.0 (5)	C11—C10—C15—C14	2.0 (4)
C2—C1—C6—C5	0.7 (5)	C8—C10—C15—C14	−177.7 (3)
Cl1—C1—C6—C5	−177.8 (3)	C20—N3—C16—C17	−1.3 (5)
N2—N1—C7—O1	−1.1 (4)	Ni1—N3—C16—C17	178.0 (3)
N2—N1—C7—C4	−179.6 (2)	N3—C16—C17—C18	0.0 (5)
Ni1—O1—C7—N1	2.4 (3)	C16—C17—C18—C19	1.5 (5)
Ni1—O1—C7—C4	−179.08 (19)	C17—C18—C19—C20	−1.8 (5)
C3—C4—C7—N1	171.6 (3)	C16—N3—C20—C19	1.0 (4)
C5—C4—C7—N1	−8.4 (4)	Ni1—N3—C20—C19	−178.3 (2)
C3—C4—C7—O1	−7.0 (4)	C18—C19—C20—N3	0.5 (5)
C5—C4—C7—O1	173.0 (3)

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₀BrClNO₂)(C₅H₅N)]
M_r	503.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	278
a, b, c (Å)	32.430 (4), 6.0816 (8), 22.865 (3)
β (°)	121.422 (2)
V (Å³)	3848.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.25
Crystal size (mm)	0.18 × 0.13 × 0.10

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.581, 0.723
No. of measured, independent and observed [I > 2σ(I)] reflections	9680, 3401, 2651
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.080, 1.02
No. of reflections	3401
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Postgraduate Foundation of Sichuan University of Science and Engineering (No.Y05–2–09).

References

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