Diaqua­[3,5-bis­(4-pyrid­yl)-1H-1,2,4-triazole-κN3](pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)nickel(II)

Cheng, F.-J.; Wang, Y.-S.; Liu, Y.-C.

doi:10.1107/S1600536810053687

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m137

doi:10.1107/S1600536810053687

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Diaqua[3,5-bis(4-pyridyl)-1H-1,2,4-triazole-κN³](pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)nickel(II)

Feng-Jie Cheng,^a Yi-Sen Wang ^b and Yan-Cheng Liu ^a ^*

^aKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, People's Republic of China, and ^bPetrochemical Research Institute of PetroChina Co. Ltd, Beijing 100195, People's Republic of China
^*Correspondence e-mail: ycliugxnu@yahoo.cn

(Received 9 December 2010; accepted 21 December 2010; online 8 January 2011)

In the title compound, [Ni(C₇H₃NO₄)(C₁₂H₉N₅)(H₂O)₂], the Ni^II atom is coordinated in a distorted octahedral geometry by one N and two O atoms from a pyridine-2,6-dicarboxylate ligand, one N atom from a 3,5-bis(4-pyridyl)-1H-1,2,4-triazole ligand in equatorial positions and two water molecules in axial positions. The crystal packing is consolidated by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For synthesis of the 1H-3,5-bis(4-pyridyl)-1,2,4-triazole (BPT) ligand, see: Liu et al. (2004 ). For BPT–metal complexes, see: Huang et al. (2010a ,b ).

Experimental

Crystal data

[Ni(C₇H₃NO₄)(C₁₂H₉N₅)(H₂O)₂]
M_r = 483.07
Monoclinic, C 2/c
a = 26.434 (5) Å
b = 6.0190 (12) Å
c = 26.170 (5) Å
β = 105.69 (3)°
V = 4008.7 (13) Å³
Z = 8
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.32 × 0.21 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.768, T_max = 0.910
10662 measured reflections
3534 independent reflections
2669 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.104
S = 1.11
3534 reflections
310 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O4ⁱ	0.88 (4)	1.81 (4)	2.685 (5)	179 (7)
O5—H5B⋯O1ⁱⁱ	0.86 (4)	1.87 (4)	2.718 (5)	168 (5)
O5—H5C⋯O2ⁱⁱⁱ	0.86 (4)	1.89 (4)	2.705 (5)	160 (4)
O6—H6B⋯N6^iv	0.87 (4)	1.93 (4)	2.781 (5)	167 (6)
O6—H6C⋯O3^v	0.86 (4)	2.39 (4)	3.246 (5)	169 (8)
O6—H6C⋯O4^v	0.86 (4)	2.41 (7)	3.081 (5)	135 (6)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) x, y-1, z; (iv) $[-x+1, y+1, -z+{\script{1\over 2}}]$ ; (v) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053687/cv5017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053687/cv5017Isup2.hkl

checkCIF report

Comment top

As a contribution to structural studies of coordination abilities of 1H-3,5-bis(4-pyridyl)-1,2,4-triazole (BPT) ligand (Huang et al., 2010a,b), we present here the crystal structure of the title compound (Fig. 1)- a new nickel(II) complex with the BPT and pyridine-2,6-dicarboxylate(PDC) ligands.

Within the title compound, the nickel(II) center is six-coordinated respectively by two carboxylic O atoms [Ni1—O1 2.112 (3) Å, Ni1—O3 2.103 (3) Å,] and one N atom of PDC [Ni1—N1 1.989 (3) Å], as well as one N atom of BPT ligand [Ni1—N2 2.054 (3) Å], from the equatorial orientation, while two O atoms of two H₂O occupy the axial positions. Nickel(II) center shows a distorted octahedral coordination geometries, with bond angles of N1—Ni1—N2 175.31 (14)°, O1—Ni1—O3 156.12 (10) ° and O5—Ni1—O6 176.93 (14)°, respectively. Viewed from the whole crystal structure, each complex is linked together by intermolecular O—H···O hydrogen bonds from H₂O and carboxyl of PDC to form a supramolecular structure.

Related literature top

For synthesis of the 1H-3,5-bis(4-pyridyl)-1,2,4-triazole (BPT) ligand, see: Liu et al. (2004). For BPT–metal complexes, see: Huang et al. (2010a,b).

Experimental top

1H-3,5-bis(4-pyridyl)-1,2,4-triazole (BPT) was prepared according to the literature (Liu et al., 2004). A mixture of pyridine-2,6-dicarboxylic acid (0.084 g, 0.5 mmol), Ni(NO₃)₂.6H₂O (0.145 g, 0.5 mmol), NaOH (0.040 g, 1 mmol), BPT (0.112 g, 0.5 mmol), ethanol (0.1 ml), and H₂O (10 ml) was enclosed in a Teflon-lined autoclave under autogenous pressure at 383 K for 4 days after stirring. Red block crystals were then obtained with yield of 47% (based on Ni^II). Single crystals fit for X-ray diffraction analysis was picked out for measurement. Elemental analysis calculated for C₁₉H₁₆N₆NiO₆: C, 47.20; H, 3.31; N, 17.39. Found: C, 46.97; H, 3.51; N, 17.21.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Diaqua[3,5-bis(4-pyridyl)-1H-1,2,4-triazole-κN³](pyridine- 2,6-dicarboxylato-κ³O²,N,O⁶)nickel(II) top

Crystal data top

[Ni(C₇H₃NO₄)(C₁₂H₉N₅)(H₂O)₂]	F(000) = 1984
M_r = 483.07	D_x = 1.601 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.434 (5) Å	θ = 1.5–25.1°
b = 6.0190 (12) Å	µ = 1.02 mm⁻¹
c = 26.170 (5) Å	T = 293 K
β = 105.69 (3)°	Block, green
V = 4008.7 (13) Å³	0.32 × 0.21 × 0.11 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	2669 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
phi and ω scans	θ_max = 25.1°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
T_min = 0.768, T_max = 0.910	k = −6→7
10662 measured reflections	l = −31→30

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0251P)² + 7.5822P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
3534 reflections	Δρ_max = 0.33 e Å⁻³
310 parameters	Δρ_min = −0.33 e Å⁻³
7 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: 0.00023 (7)

Crystal data top

[Ni(C₇H₃NO₄)(C₁₂H₉N₅)(H₂O)₂]	V = 4008.7 (13) Å³
M_r = 483.07	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.434 (5) Å	µ = 1.02 mm⁻¹
b = 6.0190 (12) Å	T = 293 K
c = 26.170 (5) Å	0.32 × 0.21 × 0.11 mm
β = 105.69 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3534 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2669 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.910	R_int = 0.071
10662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	7 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.33 e Å⁻³
3534 reflections	Δρ_min = −0.33 e Å⁻³
310 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Ni1	0.226457 (19)	0.64878 (9)	0.08540 (2)	0.02533 (18)
C1	0.16122 (16)	0.9930 (7)	0.02297 (17)	0.0284 (10)
C2	0.12404 (14)	0.8314 (7)	0.03879 (16)	0.0246 (9)
C3	0.06954 (15)	0.8470 (7)	0.02545 (18)	0.0350 (11)
H3A	0.0521	0.9624	0.0043	0.042*
C4	0.04206 (16)	0.6862 (8)	0.04454 (19)	0.0412 (12)
H4A	0.0056	0.6929	0.0363	0.049*
C5	0.06859 (15)	0.5162 (7)	0.07569 (18)	0.0341 (11)
H5A	0.0504	0.4075	0.0887	0.041*
C6	0.12286 (14)	0.5098 (7)	0.08726 (16)	0.0240 (10)
C7	0.16017 (15)	0.3376 (7)	0.11997 (16)	0.0277 (10)
C8	0.34025 (16)	0.7559 (7)	0.09586 (18)	0.0354 (11)
H8A	0.3270	0.8909	0.0807	0.042*
C9	0.39403 (16)	0.7200 (7)	0.10786 (18)	0.0334 (11)
H9A	0.4161	0.8294	0.1009	0.040*
C10	0.41453 (15)	0.5203 (7)	0.13023 (17)	0.0296 (10)
C11	0.37953 (15)	0.3656 (7)	0.13924 (18)	0.0364 (11)
H11A	0.3916	0.2291	0.1543	0.044*
C12	0.32645 (16)	0.4132 (7)	0.12595 (19)	0.0361 (12)
H12A	0.3036	0.3052	0.1320	0.043*
C13	0.47160 (15)	0.4758 (7)	0.14512 (17)	0.0299 (10)
C14	0.54546 (15)	0.3328 (8)	0.17986 (16)	0.0302 (10)
C15	0.58930 (16)	0.1971 (7)	0.21043 (17)	0.0318 (11)
C16	0.64134 (17)	0.2613 (8)	0.2184 (2)	0.0485 (14)
H16A	0.6497	0.3918	0.2035	0.058*
C17	0.68063 (18)	0.1269 (9)	0.2492 (2)	0.0579 (16)
H17A	0.7153	0.1726	0.2544	0.070*
C18	0.62206 (18)	−0.1208 (8)	0.26260 (19)	0.0441 (13)
H18A	0.6149	−0.2535	0.2774	0.053*
C19	0.57996 (17)	0.0004 (8)	0.23279 (18)	0.0388 (12)
H19A	0.5458	−0.0507	0.2280	0.047*
N1	0.14859 (11)	0.6669 (5)	0.06894 (13)	0.0231 (8)
N2	0.30646 (12)	0.6050 (6)	0.10502 (14)	0.0282 (9)
N3	0.49458 (12)	0.3023 (6)	0.17511 (14)	0.0329 (9)
N4	0.50503 (12)	0.6110 (6)	0.13012 (15)	0.0363 (10)
N5	0.55201 (13)	0.5164 (6)	0.15348 (15)	0.0352 (10)
N6	0.67239 (15)	−0.0606 (7)	0.27162 (16)	0.0473 (11)
O1	0.20996 (10)	0.9403 (4)	0.03895 (11)	0.0304 (7)
O2	0.14263 (11)	1.1605 (5)	−0.00256 (12)	0.0382 (8)
O3	0.20889 (10)	0.3681 (5)	0.12533 (11)	0.0312 (7)
O4	0.14157 (11)	0.1758 (5)	0.13800 (13)	0.0427 (8)
O5	0.21976 (13)	0.4697 (5)	0.01727 (13)	0.0394 (8)
O6	0.23372 (12)	0.8463 (6)	0.15262 (13)	0.0394 (8)
H5C	0.1995 (14)	0.360 (5)	0.0075 (17)	0.055 (16)*
H6B	0.2635 (11)	0.861 (8)	0.1761 (15)	0.070 (19)*
H5B	0.2419 (14)	0.479 (7)	−0.0008 (16)	0.060 (17)*
H5	0.5810 (13)	0.575 (8)	0.147 (2)	0.076 (19)*
H6C	0.222 (2)	0.977 (5)	0.145 (3)	0.17 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0181 (3)	0.0257 (3)	0.0334 (3)	−0.0014 (3)	0.0092 (2)	0.0005 (3)
C1	0.030 (3)	0.029 (3)	0.024 (3)	−0.004 (2)	0.004 (2)	−0.003 (2)
C2	0.024 (2)	0.023 (2)	0.027 (2)	−0.0006 (19)	0.0068 (19)	−0.001 (2)
C3	0.026 (2)	0.029 (2)	0.046 (3)	0.003 (2)	0.003 (2)	0.007 (2)
C4	0.020 (2)	0.044 (3)	0.059 (3)	0.001 (2)	0.010 (2)	0.007 (3)
C5	0.024 (2)	0.033 (3)	0.048 (3)	−0.006 (2)	0.013 (2)	0.010 (2)
C6	0.021 (2)	0.025 (2)	0.027 (2)	−0.0019 (18)	0.0075 (19)	0.001 (2)
C7	0.028 (2)	0.027 (2)	0.030 (2)	−0.002 (2)	0.011 (2)	−0.001 (2)
C8	0.027 (2)	0.032 (3)	0.045 (3)	0.002 (2)	0.005 (2)	0.009 (2)
C9	0.027 (2)	0.029 (3)	0.046 (3)	−0.0044 (19)	0.013 (2)	0.007 (2)
C10	0.023 (2)	0.032 (3)	0.034 (3)	−0.0009 (19)	0.008 (2)	0.000 (2)
C11	0.026 (2)	0.030 (3)	0.056 (3)	0.003 (2)	0.014 (2)	0.012 (2)
C12	0.023 (2)	0.033 (3)	0.054 (3)	−0.001 (2)	0.012 (2)	0.010 (2)
C13	0.020 (2)	0.038 (3)	0.032 (3)	0.002 (2)	0.007 (2)	0.008 (2)
C14	0.022 (2)	0.037 (3)	0.032 (3)	0.003 (2)	0.007 (2)	0.010 (2)
C15	0.027 (2)	0.040 (3)	0.029 (3)	0.003 (2)	0.009 (2)	0.007 (2)
C16	0.026 (3)	0.055 (3)	0.064 (4)	0.005 (2)	0.013 (3)	0.034 (3)
C17	0.027 (3)	0.072 (4)	0.073 (4)	0.007 (3)	0.011 (3)	0.033 (3)
C18	0.044 (3)	0.042 (3)	0.044 (3)	0.004 (2)	0.009 (3)	0.012 (3)
C19	0.030 (3)	0.044 (3)	0.041 (3)	0.001 (2)	0.006 (2)	0.007 (2)
N1	0.0214 (18)	0.0195 (18)	0.0280 (19)	−0.0029 (16)	0.0057 (16)	−0.0002 (17)
N2	0.0193 (18)	0.031 (2)	0.033 (2)	−0.0017 (16)	0.0054 (16)	−0.0002 (17)
N3	0.0222 (19)	0.038 (2)	0.040 (2)	0.0020 (17)	0.0104 (18)	0.0104 (19)
N4	0.0206 (19)	0.038 (2)	0.052 (3)	0.0041 (17)	0.0113 (18)	0.015 (2)
N5	0.017 (2)	0.039 (2)	0.049 (3)	0.0041 (17)	0.0074 (19)	0.014 (2)
N6	0.035 (2)	0.057 (3)	0.047 (3)	0.012 (2)	0.005 (2)	0.021 (2)
O1	0.0237 (16)	0.0296 (17)	0.0403 (19)	−0.0028 (13)	0.0129 (14)	0.0045 (15)
O2	0.0390 (18)	0.0273 (17)	0.0454 (19)	−0.0032 (15)	0.0063 (15)	0.0097 (17)
O3	0.0206 (15)	0.0348 (17)	0.0394 (18)	0.0019 (14)	0.0103 (14)	0.0095 (15)
O4	0.0305 (17)	0.0379 (19)	0.061 (2)	−0.0006 (15)	0.0153 (16)	0.0213 (18)
O5	0.044 (2)	0.036 (2)	0.046 (2)	−0.0169 (17)	0.0237 (18)	−0.0124 (17)
O6	0.0326 (19)	0.044 (2)	0.036 (2)	0.0048 (17)	−0.0016 (16)	−0.0132 (18)

Geometric parameters (Å, º) top

Ni1—N1	1.989 (3)	C10—C13	1.477 (5)
Ni1—O5	2.050 (3)	C11—C12	1.381 (5)
Ni1—N2	2.054 (3)	C11—H11A	0.9300
Ni1—O6	2.088 (3)	C12—N2	1.325 (5)
Ni1—O3	2.103 (3)	C12—H12A	0.9300
Ni1—O1	2.112 (3)	C13—N4	1.336 (5)
C1—O2	1.236 (5)	C13—N3	1.348 (5)
C1—O1	1.282 (4)	C14—N3	1.330 (5)
C1—C2	1.518 (5)	C14—N5	1.339 (5)
C2—N1	1.322 (5)	C14—C15	1.466 (6)
C2—C3	1.391 (5)	C15—C19	1.372 (6)
C3—C4	1.382 (6)	C15—C16	1.389 (6)
C3—H3A	0.9300	C16—C17	1.389 (6)
C4—C5	1.376 (6)	C16—H16A	0.9300
C4—H4A	0.9300	C17—N6	1.317 (6)
C5—C6	1.384 (5)	C17—H17A	0.9300
C5—H5A	0.9300	C18—N6	1.337 (5)
C6—N1	1.328 (5)	C18—C19	1.382 (6)
C6—C7	1.524 (6)	C18—H18A	0.9300
C7—O4	1.241 (5)	C19—H19A	0.9300
C7—O3	1.271 (4)	N4—N5	1.352 (4)
C8—N2	1.340 (5)	N5—H5	0.901 (19)
C8—C9	1.387 (5)	O5—H5C	0.842 (18)
C8—H8A	0.9300	O5—H5B	0.848 (18)
C9—C10	1.382 (6)	O6—H6B	0.861 (19)
C9—H9A	0.9300	O6—H6C	0.854 (19)
C10—C11	1.377 (5)

N1—Ni1—O5	89.97 (13)	C10—C11—H11A	120.0
N1—Ni1—N2	175.33 (14)	C12—C11—H11A	120.0
O5—Ni1—N2	89.48 (14)	N2—C12—C11	123.3 (4)
N1—Ni1—O6	90.30 (13)	N2—C12—H12A	118.3
O5—Ni1—O6	177.00 (14)	C11—C12—H12A	118.3
N2—Ni1—O6	90.49 (13)	N4—C13—N3	114.4 (3)
N1—Ni1—O3	78.29 (12)	N4—C13—C10	121.4 (4)
O5—Ni1—O3	91.78 (12)	N3—C13—C10	124.2 (4)
N2—Ni1—O3	97.09 (12)	N3—C14—N5	109.5 (4)
O6—Ni1—O3	91.20 (13)	N3—C14—C15	127.2 (4)
N1—Ni1—O1	77.83 (12)	N5—C14—C15	123.2 (4)
O5—Ni1—O1	88.88 (13)	C19—C15—C16	117.4 (4)
N2—Ni1—O1	106.79 (12)	C19—C15—C14	120.4 (4)
O6—Ni1—O1	88.25 (13)	C16—C15—C14	122.1 (4)
O3—Ni1—O1	156.11 (10)	C15—C16—C17	118.7 (4)
O2—C1—O1	126.6 (4)	C15—C16—H16A	120.7
O2—C1—C2	118.6 (4)	C17—C16—H16A	120.7
O1—C1—C2	114.9 (4)	N6—C17—C16	124.7 (4)
N1—C2—C3	120.6 (4)	N6—C17—H17A	117.6
N1—C2—C1	113.2 (3)	C16—C17—H17A	117.6
C3—C2—C1	126.3 (4)	N6—C18—C19	124.6 (5)
C4—C3—C2	118.2 (4)	N6—C18—H18A	117.7
C4—C3—H3A	120.9	C19—C18—H18A	117.7
C2—C3—H3A	120.9	C15—C19—C18	119.1 (4)
C5—C4—C3	120.1 (4)	C15—C19—H19A	120.5
C5—C4—H4A	120.0	C18—C19—H19A	120.5
C3—C4—H4A	120.0	C2—N1—C6	122.2 (3)
C4—C5—C6	118.8 (4)	C2—N1—Ni1	118.9 (3)
C4—C5—H5A	120.6	C6—N1—Ni1	118.9 (3)
C6—C5—H5A	120.6	C12—N2—C8	117.0 (3)
N1—C6—C5	120.2 (4)	C12—N2—Ni1	118.9 (3)
N1—C6—C7	111.7 (3)	C8—N2—Ni1	124.0 (3)
C5—C6—C7	128.1 (4)	C14—N3—C13	103.5 (3)
O4—C7—O3	124.5 (4)	C13—N4—N5	102.2 (3)
O4—C7—C6	119.0 (3)	C14—N5—N4	110.5 (3)
O3—C7—C6	116.5 (4)	C14—N5—H5	131 (3)
N2—C8—C9	123.1 (4)	N4—N5—H5	118 (3)
N2—C8—H8A	118.5	C17—N6—C18	115.5 (4)
C9—C8—H8A	118.5	C1—O1—Ni1	115.2 (2)
C10—C9—C8	119.5 (4)	C7—O3—Ni1	114.5 (3)
C10—C9—H9A	120.3	Ni1—O5—H5C	125 (3)
C8—C9—H9A	120.3	Ni1—O5—H5B	123 (3)
C11—C10—C9	117.1 (4)	H5C—O5—H5B	111 (3)
C11—C10—C13	121.2 (4)	Ni1—O6—H6B	121 (3)
C9—C10—C13	121.7 (4)	Ni1—O6—H6C	112 (5)
C10—C11—C12	120.0 (4)	H6B—O6—H6C	107 (3)

O2—C1—C2—N1	−175.7 (4)	O1—Ni1—N1—C2	1.3 (3)
O1—C1—C2—N1	3.1 (5)	O5—Ni1—N1—C6	90.5 (3)
O2—C1—C2—C3	2.9 (6)	N2—Ni1—N1—C6	7.3 (19)
O1—C1—C2—C3	−178.3 (4)	O6—Ni1—N1—C6	−92.5 (3)
N1—C2—C3—C4	0.0 (6)	O3—Ni1—N1—C6	−1.3 (3)
C1—C2—C3—C4	−178.5 (4)	O1—Ni1—N1—C6	179.4 (3)
C2—C3—C4—C5	−0.2 (7)	C11—C12—N2—C8	1.2 (7)
C3—C4—C5—C6	−0.1 (7)	C11—C12—N2—Ni1	178.3 (3)
C4—C5—C6—N1	0.7 (6)	C9—C8—N2—C12	−0.8 (7)
C4—C5—C6—C7	−179.1 (4)	C9—C8—N2—Ni1	−177.8 (3)
N1—C6—C7—O4	−177.3 (4)	N1—Ni1—N2—C12	4.0 (19)
C5—C6—C7—O4	2.5 (7)	O5—Ni1—N2—C12	−79.3 (3)
N1—C6—C7—O3	0.5 (5)	O6—Ni1—N2—C12	103.7 (3)
C5—C6—C7—O3	−179.7 (4)	O3—Ni1—N2—C12	12.5 (3)
N2—C8—C9—C10	0.1 (7)	O1—Ni1—N2—C12	−167.9 (3)
C8—C9—C10—C11	0.2 (7)	N1—Ni1—N2—C8	−179 (100)
C8—C9—C10—C13	−178.3 (4)	O5—Ni1—N2—C8	97.7 (4)
C9—C10—C11—C12	0.1 (7)	O6—Ni1—N2—C8	−79.3 (4)
C13—C10—C11—C12	178.6 (4)	O3—Ni1—N2—C8	−170.6 (3)
C10—C11—C12—N2	−0.8 (7)	O1—Ni1—N2—C8	9.0 (4)
C11—C10—C13—N4	170.7 (4)	N5—C14—N3—C13	−0.3 (5)
C9—C10—C13—N4	−10.8 (7)	C15—C14—N3—C13	177.4 (4)
C11—C10—C13—N3	−10.5 (7)	N4—C13—N3—C14	1.0 (5)
C9—C10—C13—N3	168.0 (4)	C10—C13—N3—C14	−177.8 (4)
N3—C14—C15—C19	8.3 (7)	N3—C13—N4—N5	−1.3 (5)
N5—C14—C15—C19	−174.3 (4)	C10—C13—N4—N5	177.6 (4)
N3—C14—C15—C16	−171.1 (5)	N3—C14—N5—N4	−0.5 (5)
N5—C14—C15—C16	6.3 (7)	C15—C14—N5—N4	−178.4 (4)
C19—C15—C16—C17	−1.3 (7)	C13—N4—N5—C14	1.1 (5)
C14—C15—C16—C17	178.1 (5)	C16—C17—N6—C18	0.8 (8)
C15—C16—C17—N6	0.3 (9)	C19—C18—N6—C17	−0.9 (7)
C16—C15—C19—C18	1.1 (7)	O2—C1—O1—Ni1	176.6 (3)
C14—C15—C19—C18	−178.2 (4)	C2—C1—O1—Ni1	−2.0 (4)
N6—C18—C19—C15	−0.1 (7)	N1—Ni1—O1—C1	0.5 (3)
C3—C2—N1—C6	0.6 (6)	O5—Ni1—O1—C1	90.7 (3)
C1—C2—N1—C6	179.3 (3)	N2—Ni1—O1—C1	179.9 (3)
C3—C2—N1—Ni1	178.6 (3)	O6—Ni1—O1—C1	−90.2 (3)
C1—C2—N1—Ni1	−2.7 (4)	O3—Ni1—O1—C1	−1.1 (5)
C5—C6—N1—C2	−1.0 (6)	O4—C7—O3—Ni1	176.1 (3)
C7—C6—N1—C2	178.8 (3)	C6—C7—O3—Ni1	−1.6 (4)
C5—C6—N1—Ni1	−178.9 (3)	N1—Ni1—O3—C7	1.6 (3)
C7—C6—N1—Ni1	0.9 (4)	O5—Ni1—O3—C7	−88.0 (3)
O5—Ni1—N1—C2	−87.5 (3)	N2—Ni1—O3—C7	−177.7 (3)
N2—Ni1—N1—C2	−170.7 (16)	O6—Ni1—O3—C7	91.6 (3)
O6—Ni1—N1—C2	89.5 (3)	O1—Ni1—O3—C7	3.2 (5)
O3—Ni1—N1—C2	−179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4ⁱ	0.88 (4)	1.81 (4)	2.685 (5)	179 (7)
O5—H5B···O1ⁱⁱ	0.86 (4)	1.87 (4)	2.718 (5)	168 (5)
O5—H5C···O2ⁱⁱⁱ	0.86 (4)	1.89 (4)	2.705 (5)	160 (4)
O6—H6B···N6^iv	0.87 (4)	1.93 (4)	2.781 (5)	167 (6)
O6—H6C···O3^v	0.86 (4)	2.39 (4)	3.246 (5)	169 (8)
O6—H6C···O4^v	0.86 (4)	2.41 (7)	3.081 (5)	135 (6)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₃NO₄)(C₁₂H₉N₅)(H₂O)₂]
M_r	483.07
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	26.434 (5), 6.0190 (12), 26.170 (5)
β (°)	105.69 (3)
V (Å³)	4008.7 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.32 × 0.21 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.768, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	10662, 3534, 2669
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.104, 1.11
No. of reflections	3534
No. of parameters	310
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4ⁱ	0.88 (4)	1.81 (4)	2.685 (5)	179 (7)
O5—H5B···O1ⁱⁱ	0.86 (4)	1.87 (4)	2.718 (5)	168 (5)
O5—H5C···O2ⁱⁱⁱ	0.86 (4)	1.89 (4)	2.705 (5)	160 (4)
O6—H6B···N6^iv	0.87 (4)	1.93 (4)	2.781 (5)	167 (6)
O6—H6C···O3^v	0.86 (4)	2.39 (4)	3.246 (5)	169 (8)
O6—H6C···O4^v	0.86 (4)	2.41 (7)	3.081 (5)	135 (6)

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20861002), the Natural Science Foundation of Guangxi Province (grant Nos. 0991012Z, 0991003), the Education Department Foundation of Guangxi Province (grant No. 200807MS014), as well as the Key Laboratory Open Fund of the Ministry of Education and the Doctoral Fund of Guangxi Normal University for financial support. We also thank Dr F.-P. Huang for assistance with the crystallographic analysis.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, F.-P., Tian, J.-L., Li, D.-D., Chen, G.-J., Gu, W., Yan, S.-P., Liu, X., Liao, D.-Z. & Cheng, P. (2010a). CrystEngComm, 12, 395–400. Web of Science CSD CrossRef Google Scholar
Huang, F.-P., Tian, J.-L., Li, D.-D., Chen, G.-J., Gu, W., Yan, S.-P., Liu, X., Liao, D.-Z. & Cheng, P. (2010b). Inorg. Chem. 49, 2525–2529. Web of Science CSD CrossRef CAS PubMed Google Scholar
Liu, H. B., Gao, J. M., Maynard, L., Saito, Y. D. & Kool, E. T. (2004). J. Am. Chem. Soc. 126, 1102–1109. Web of Science 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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