Bis(methanol-κO)bis­{5-(pyridin-2-yl-κN)-3-[4-(pyridin-4-yl)phen­yl]-1H-1,2,4-triazol-1-ido-κN1}cobalt(II)

Peng, Z.; Xia, L.; Dong, W.-W.

doi:10.1107/S241431461601316X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161316

doi:10.1107/S241431461601316X

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Bis(methanol-κO)bis{5-(pyridin-2-yl-κN)-3-[4-(pyridin-4-yl)phenyl]-1H-1,2,4-triazol-1-ido-κN¹}cobalt(II)

Zhen Peng,^a Liang Xia ^a ^* and Wen-Wen Dong ^a ^*

^aCollege of Materials and Chemical Engineering, China Three Gorges University, YiChang 443002, People's Republic of China
^*Correspondence e-mail: 18162391708@163.com, dongww1@126.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 14 July 2016; accepted 16 August 2016; online 26 August 2016)

The asymmetric unit of the title Co^II complex, [Co(C₁₈H₁₂N₅)₂(CH₃OH)₂], contains one half-molecule, and the complex is completed by application of an inversion centre. The Co^II cation is coordinated by two deprotonated 1,2,4-triazole-based ligands, and two methanol molecules, in an N₄O₂ octahedral coordination geometry. Four N atoms are placed in the equatorial plane, while trans-methanol molecules occupy the axial positions. In the crystal, neighbouring complexes are linked via O—H⋯N hydrogen-bonding interactions, involving the methanol as donor and non-coordinating N triazole sites as acceptor groups, forming a two-dimensional network parallel to (100).

Keywords: crystal structure; triazole; cobalt; hydrogen bonding.

CCDC reference: 1487833

Structure description

The single-crystal X-ray diffraction analysis of the title complex reveals that the Co^II atom is six-coordinate. The metal is located on an inversion centre, forming a centrosymmetric complex with coordinating methanol molecules occupying trans sites (Fig. 1). The isotypic complex bearing water as ligands in place of methanol has been reported (Li, 2013a ). However, for the water-containing complex, the triazole derivative was not planar, while this ligand is almost planar in the title complex. The same triazole derivative has also been used for the synthesis of Fe^II and Zn^II mononuclear complexes (Li, 2013b ,c ), and polymeric species (Zhang et al., 2012 , 2013 ). Multidentate ligands containing 1,2,4-trizaole heterocycle and other N-donor heterocyclic groups are frequently used in the preparation of metal complexes (Gong et al., 2014 ; Liu et al., 2015 ; Dong et al., 2016 ).

Figure 1
The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

The crystal structure features intermolecular O—H⋯N hydrogen bonds (Table 1) involving the hydroxyl group of MeOH and one triazole N atom, forming a two-dimensional network parallel to (100).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4ⁱ	0.85 (1)	1.92 (2)	2.760 (5)	168 (5)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Synthesis and crystallization

A mixture of 5-(pyridin-2-yl)-3-[4-(pyridin-4-yl)phenyl]-1H-1,2,4-triazole (0.15 mmol, 0.0448 g), cobalt(II) nitrate hexahydrate (0.10 mmol, 0.0234 g) and CH₃OH (12 ml) were placed in a Teflon-lined stainless steel vessel, heated to 437 K for 3 d, followed by slow cooling to room temperature. Yellow prismatic crystals were obtained. Analysis calculated for C₃₈H₃₂CoN₁₀O₂: C 63.36, H 4.44, N 19.45%; found: C 63.52, H 4.48, N 19.45%

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Co(C₁₈H₁₂N₅)₂(CH₄O)₂]
M_r	719.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.414 (4), 12.654 (3), 9.964 (1)
β (°)	101.43 (2)
V (Å³)	1657.8 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.57
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.880, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	17371, 3842, 2915
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.193, 1.00
No. of reflections	3842
No. of parameters	235
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.55
Computer programs: SMART and SAINT (Bruker, 2007 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1487833

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S241431461601316X/bh4009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S241431461601316X/bh4009Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (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: publCIF (Westrip, 2010).

Bis(methanol-κO)bis{5-(pyridin-2-yl-κN)-3-[4-(pyridin-4-yl)phenyl]-1H-1,2,4-triazol-1-ido-κN¹}cobalt(II) top

Crystal data top

[Co(C₁₈H₁₂N₅)₂(CH₄O)₂]	F(000) = 746
M_r = 719.67	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.414 (4) Å	Cell parameters from 3457 reflections
b = 12.654 (3) Å	θ = 2.2–27.5°
c = 9.964 (1) Å	µ = 0.57 mm⁻¹
β = 101.43 (2)°	T = 296 K
V = 1657.8 (7) Å³	Prism, yellow
Z = 2	0.23 × 0.21 × 0.18 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3842 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
φ and ω scans	θ_max = 27.7°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→17
T_min = 0.880, T_max = 0.904	k = −16→16
17371 measured reflections	l = −12→12

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0867P)² + 2.491P] where P = (F_o² + 2F_c²)/3
3842 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.43 e Å⁻³
1 restraint	Δρ_min = −0.55 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Co1	0.5000	0.5000	0.0000	0.0276 (2)
O1	0.4016 (2)	0.5716 (2)	0.1228 (3)	0.0366 (6)
H1	0.398 (4)	0.6381 (10)	0.132 (5)	0.055*
N1	0.4240 (2)	0.3508 (2)	−0.0040 (3)	0.0279 (7)
N2	0.5827 (2)	0.4245 (2)	0.1702 (3)	0.0310 (7)
N3	0.6646 (2)	0.4464 (2)	0.2708 (3)	0.0315 (7)
N4	0.6079 (2)	0.2819 (2)	0.3071 (3)	0.0282 (7)
N5	1.1509 (3)	0.3720 (4)	1.0761 (4)	0.0662 (13)
C1	0.3465 (3)	0.3180 (3)	−0.1010 (4)	0.0334 (8)
H1A	0.3178	0.3651	−0.1694	0.040*
C2	0.3072 (3)	0.2164 (3)	−0.1036 (4)	0.0387 (9)
H2A	0.2534	0.1953	−0.1725	0.046*
C3	0.3500 (3)	0.1477 (3)	−0.0015 (4)	0.0399 (10)
H3B	0.3256	0.0789	−0.0018	0.048*
C4	0.4283 (3)	0.1795 (3)	0.1010 (4)	0.0337 (8)
H4B	0.4561	0.1336	0.1714	0.040*
C5	0.4649 (3)	0.2818 (3)	0.0968 (4)	0.0255 (7)
C6	0.5516 (3)	0.3269 (3)	0.1939 (3)	0.0264 (7)
C7	0.6775 (3)	0.3599 (3)	0.3507 (4)	0.0277 (7)
C8	0.7604 (3)	0.3551 (3)	0.4717 (4)	0.0299 (8)
C9	0.8303 (3)	0.4378 (3)	0.4960 (4)	0.0364 (9)
H9A	0.8252	0.4930	0.4335	0.044*
C10	0.9068 (3)	0.4394 (3)	0.6113 (4)	0.0412 (10)
H10A	0.9520	0.4958	0.6250	0.049*
C11	0.9178 (3)	0.3579 (3)	0.7077 (4)	0.0353 (9)
C12	0.8490 (3)	0.2738 (4)	0.6814 (4)	0.0412 (10)
H12A	0.8553	0.2175	0.7426	0.049*
C13	0.7711 (3)	0.2723 (3)	0.5654 (4)	0.0358 (9)
H13A	0.7261	0.2156	0.5507	0.043*
C14	0.9990 (3)	0.3617 (4)	0.8330 (4)	0.0404 (10)
C15	1.0129 (4)	0.2820 (5)	0.9295 (5)	0.0670 (17)
H15A	0.9722	0.2220	0.9157	0.080*
C16	1.0886 (4)	0.2912 (6)	1.0489 (6)	0.076 (2)
H16A	1.0949	0.2367	1.1125	0.091*
C17	1.1400 (5)	0.4469 (5)	0.9823 (6)	0.080 (2)
H17A	1.1837	0.5046	0.9979	0.096*
C18	1.0668 (5)	0.4453 (5)	0.8609 (6)	0.0734 (18)
H18A	1.0636	0.5005	0.7986	0.088*
C19	0.3625 (4)	0.5204 (3)	0.2296 (5)	0.0445 (10)
H19A	0.3210	0.5691	0.2682	0.067*
H19B	0.4180	0.4971	0.2996	0.067*
H19C	0.3222	0.4605	0.1927	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0360 (4)	0.0185 (3)	0.0245 (4)	−0.0016 (3)	−0.0034 (3)	0.0023 (3)
O1	0.0509 (17)	0.0258 (14)	0.0336 (14)	0.0025 (12)	0.0100 (13)	−0.0025 (11)
N1	0.0338 (16)	0.0222 (15)	0.0246 (15)	−0.0017 (12)	−0.0020 (13)	0.0029 (11)
N2	0.0351 (17)	0.0245 (15)	0.0294 (16)	−0.0022 (12)	−0.0036 (14)	0.0007 (12)
N3	0.0360 (17)	0.0251 (16)	0.0290 (16)	−0.0004 (13)	−0.0043 (14)	−0.0003 (12)
N4	0.0335 (16)	0.0230 (15)	0.0265 (15)	0.0001 (12)	0.0021 (13)	0.0039 (11)
N5	0.052 (3)	0.092 (4)	0.044 (2)	−0.005 (2)	−0.015 (2)	0.002 (2)
C1	0.034 (2)	0.031 (2)	0.0311 (19)	−0.0014 (15)	−0.0019 (16)	0.0038 (15)
C2	0.039 (2)	0.037 (2)	0.034 (2)	−0.0082 (17)	−0.0060 (18)	−0.0045 (17)
C3	0.048 (2)	0.028 (2)	0.042 (2)	−0.0094 (17)	0.005 (2)	−0.0016 (16)
C4	0.041 (2)	0.0261 (19)	0.0324 (19)	−0.0020 (15)	0.0035 (17)	0.0044 (15)
C5	0.0308 (18)	0.0193 (16)	0.0257 (17)	0.0013 (13)	0.0041 (14)	0.0037 (13)
C6	0.0312 (18)	0.0228 (17)	0.0239 (17)	0.0016 (14)	0.0027 (14)	0.0030 (13)
C7	0.0321 (19)	0.0249 (17)	0.0250 (17)	0.0039 (14)	0.0031 (15)	−0.0001 (13)
C8	0.0286 (18)	0.0310 (19)	0.0281 (18)	0.0020 (14)	0.0010 (15)	−0.0012 (14)
C9	0.041 (2)	0.030 (2)	0.035 (2)	−0.0015 (16)	−0.0002 (17)	0.0049 (15)
C10	0.041 (2)	0.039 (2)	0.038 (2)	−0.0078 (18)	−0.0053 (19)	0.0011 (17)
C11	0.0308 (19)	0.045 (2)	0.0284 (19)	−0.0004 (16)	0.0015 (16)	0.0031 (16)
C12	0.042 (2)	0.046 (2)	0.031 (2)	−0.0021 (18)	−0.0049 (18)	0.0109 (18)
C13	0.037 (2)	0.039 (2)	0.0290 (19)	−0.0073 (16)	0.0007 (17)	0.0056 (16)
C14	0.036 (2)	0.049 (2)	0.034 (2)	0.0000 (18)	0.0024 (18)	0.0002 (18)
C15	0.055 (3)	0.084 (4)	0.051 (3)	−0.028 (3)	−0.015 (3)	0.023 (3)
C16	0.055 (3)	0.111 (5)	0.053 (3)	−0.022 (3)	−0.012 (3)	0.037 (3)
C17	0.083 (4)	0.073 (4)	0.062 (4)	−0.020 (3)	−0.036 (3)	0.007 (3)
C18	0.076 (4)	0.061 (4)	0.066 (4)	−0.023 (3)	−0.028 (3)	0.014 (3)
C19	0.054 (3)	0.038 (2)	0.045 (2)	−0.0061 (19)	0.017 (2)	−0.0009 (18)

Geometric parameters (Å, º) top

Co1—N2	2.067 (3)	C5—C6	1.473 (5)
Co1—N2ⁱ	2.067 (3)	C7—C8	1.471 (5)
Co1—N1ⁱ	2.142 (3)	C8—C13	1.392 (5)
Co1—N1	2.142 (3)	C8—C9	1.394 (5)
Co1—O1ⁱ	2.168 (3)	C9—C10	1.381 (6)
Co1—O1	2.168 (3)	C9—H9A	0.9300
O1—C19	1.432 (5)	C10—C11	1.396 (6)
O1—H1	0.849 (10)	C10—H10A	0.9300
N1—C1	1.338 (5)	C11—C12	1.400 (6)
N1—C5	1.362 (4)	C11—C14	1.486 (6)
N2—C6	1.339 (5)	C12—C13	1.396 (5)
N2—N3	1.361 (4)	C12—H12A	0.9300
N3—C7	1.344 (5)	C13—H13A	0.9300
N4—C6	1.353 (4)	C14—C15	1.380 (7)
N4—C7	1.369 (5)	C14—C18	1.387 (7)
N5—C16	1.314 (8)	C15—C16	1.407 (7)
N5—C17	1.320 (8)	C15—H15A	0.9300
C1—C2	1.388 (6)	C16—H16A	0.9300
C1—H1A	0.9300	C17—C18	1.399 (7)
C2—C3	1.374 (6)	C17—H17A	0.9300
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.372 (6)	C19—H19A	0.9600
C3—H3B	0.9300	C19—H19B	0.9600
C4—C5	1.388 (5)	C19—H19C	0.9600
C4—H4B	0.9300

N2—Co1—N2ⁱ	180.0	N4—C6—C5	128.5 (3)
N2—Co1—N1ⁱ	102.48 (12)	N3—C7—N4	113.6 (3)
N2ⁱ—Co1—N1ⁱ	77.52 (12)	N3—C7—C8	120.5 (3)
N2—Co1—N1	77.52 (12)	N4—C7—C8	125.9 (3)
N2ⁱ—Co1—N1	102.48 (12)	C13—C8—C9	118.2 (4)
N1ⁱ—Co1—N1	180.00 (16)	C13—C8—C7	122.8 (3)
N2—Co1—O1ⁱ	88.97 (14)	C9—C8—C7	119.0 (3)
N2ⁱ—Co1—O1ⁱ	91.03 (14)	C10—C9—C8	121.3 (4)
N1ⁱ—Co1—O1ⁱ	92.20 (13)	C10—C9—H9A	119.4
N1—Co1—O1ⁱ	87.80 (13)	C8—C9—H9A	119.4
N2—Co1—O1	91.03 (14)	C9—C10—C11	121.4 (4)
N2ⁱ—Co1—O1	88.97 (14)	C9—C10—H10A	119.3
N1ⁱ—Co1—O1	87.80 (13)	C11—C10—H10A	119.3
N1—Co1—O1	92.20 (13)	C10—C11—C12	117.2 (4)
O1ⁱ—Co1—O1	180.00 (11)	C10—C11—C14	121.0 (4)
C19—O1—Co1	125.7 (3)	C12—C11—C14	121.8 (4)
C19—O1—H1	109 (3)	C13—C12—C11	121.5 (4)
Co1—O1—H1	122 (3)	C13—C12—H12A	119.2
C1—N1—C5	118.4 (3)	C11—C12—H12A	119.2
C1—N1—Co1	125.9 (2)	C12—C13—C8	120.4 (4)
C5—N1—Co1	115.5 (2)	C12—C13—H13A	119.8
C6—N2—N3	107.0 (3)	C8—C13—H13A	119.8
C6—N2—Co1	115.8 (2)	C15—C14—C18	115.1 (4)
N3—N2—Co1	137.2 (2)	C15—C14—C11	122.6 (4)
C7—N3—N2	105.1 (3)	C18—C14—C11	122.3 (4)
C6—N4—C7	101.2 (3)	C14—C15—C16	120.3 (5)
C16—N5—C17	115.8 (5)	C14—C15—H15A	119.8
N1—C1—C2	122.6 (3)	C16—C15—H15A	119.8
N1—C1—H1A	118.7	N5—C16—C15	124.2 (5)
C2—C1—H1A	118.7	N5—C16—H16A	117.9
C3—C2—C1	118.0 (4)	C15—C16—H16A	117.9
C3—C2—H2A	121.0	N5—C17—C18	124.2 (6)
C1—C2—H2A	121.0	N5—C17—H17A	117.9
C4—C3—C2	120.8 (4)	C18—C17—H17A	117.9
C4—C3—H3B	119.6	C14—C18—C17	120.3 (5)
C2—C3—H3B	119.6	C14—C18—H18A	119.8
C3—C4—C5	118.3 (4)	C17—C18—H18A	119.8
C3—C4—H4B	120.8	O1—C19—H19A	109.5
C5—C4—H4B	120.8	O1—C19—H19B	109.5
N1—C5—C4	121.8 (3)	H19A—C19—H19B	109.5
N1—C5—C6	112.7 (3)	O1—C19—H19C	109.5
C4—C5—C6	125.5 (3)	H19A—C19—H19C	109.5
N2—C6—N4	113.2 (3)	H19B—C19—H19C	109.5
N2—C6—C5	118.3 (3)

N2—Co1—O1—C19	−40.9 (3)	C7—N4—C6—N2	−0.7 (4)
N2ⁱ—Co1—O1—C19	139.1 (3)	C7—N4—C6—C5	178.2 (4)
N1ⁱ—Co1—O1—C19	−143.3 (3)	N1—C5—C6—N2	−3.0 (5)
N1—Co1—O1—C19	36.7 (3)	C4—C5—C6—N2	175.0 (4)
N2—Co1—N1—C1	−176.5 (3)	N1—C5—C6—N4	178.2 (4)
N2ⁱ—Co1—N1—C1	3.5 (3)	C4—C5—C6—N4	−3.8 (6)
O1ⁱ—Co1—N1—C1	−87.1 (3)	N2—N3—C7—N4	0.2 (4)
O1—Co1—N1—C1	92.9 (3)	N2—N3—C7—C8	180.0 (3)
N2—Co1—N1—C5	−1.8 (3)	C6—N4—C7—N3	0.3 (4)
N2ⁱ—Co1—N1—C5	178.2 (3)	C6—N4—C7—C8	−179.5 (4)
O1ⁱ—Co1—N1—C5	87.7 (3)	N3—C7—C8—C13	173.3 (4)
O1—Co1—N1—C5	−92.3 (3)	N4—C7—C8—C13	−6.9 (6)
N1ⁱ—Co1—N2—C6	−179.9 (3)	N3—C7—C8—C9	−5.1 (6)
N1—Co1—N2—C6	0.1 (3)	N4—C7—C8—C9	174.7 (4)
O1ⁱ—Co1—N2—C6	−87.9 (3)	C13—C8—C9—C10	−1.4 (6)
O1—Co1—N2—C6	92.1 (3)	C7—C8—C9—C10	177.1 (4)
N1ⁱ—Co1—N2—N3	−0.3 (4)	C8—C9—C10—C11	0.4 (7)
N1—Co1—N2—N3	179.7 (4)	C9—C10—C11—C12	1.1 (7)
O1ⁱ—Co1—N2—N3	91.7 (4)	C9—C10—C11—C14	−178.5 (4)
O1—Co1—N2—N3	−88.3 (4)	C10—C11—C12—C13	−1.5 (7)
C6—N2—N3—C7	−0.6 (4)	C14—C11—C12—C13	178.1 (4)
Co1—N2—N3—C7	179.8 (3)	C11—C12—C13—C8	0.5 (7)
C5—N1—C1—C2	−0.8 (6)	C9—C8—C13—C12	0.9 (6)
Co1—N1—C1—C2	173.8 (3)	C7—C8—C13—C12	−177.4 (4)
N1—C1—C2—C3	0.3 (7)	C10—C11—C14—C15	−179.1 (5)
C1—C2—C3—C4	0.9 (7)	C12—C11—C14—C15	1.3 (7)
C2—C3—C4—C5	−1.7 (6)	C10—C11—C14—C18	0.4 (7)
C1—N1—C5—C4	0.0 (5)	C12—C11—C14—C18	−179.2 (5)
Co1—N1—C5—C4	−175.2 (3)	C18—C14—C15—C16	2.8 (9)
C1—N1—C5—C6	178.1 (3)	C11—C14—C15—C16	−177.7 (5)
Co1—N1—C5—C6	3.0 (4)	C17—N5—C16—C15	−0.7 (10)
C3—C4—C5—N1	1.3 (6)	C14—C15—C16—N5	−1.3 (11)
C3—C4—C5—C6	−176.6 (4)	C16—N5—C17—C18	1.1 (11)
N3—N2—C6—N4	0.8 (4)	C15—C14—C18—C17	−2.5 (9)
Co1—N2—C6—N4	−179.5 (2)	C11—C14—C18—C17	178.0 (6)
N3—N2—C6—C5	−178.2 (3)	N5—C17—C18—C14	0.6 (12)
Co1—N2—C6—C5	1.5 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4ⁱⁱ	0.85 (1)	1.92 (2)	2.760 (5)	168 (5)

Symmetry code: (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (No. 21301106) and the Project of Hubei Provincial Education Office (No. Q20141201).

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