Tris(ethane-1,2-diamine-κ2N,N′)nickel(II) 5-hy­droxy­isophthalate monohydrate

Wang, S.-H.; Zhang, B.; Wang, C.; Xu, G.-Q.; Xie, Y.

doi:10.1107/S1600536811001449

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m257-m258

doi:10.1107/S1600536811001449

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Tris(ethane-1,2-diamine-κ²N,N′)nickel(II) 5-hydroxyisophthalate monohydrate

Shu-Hong Wang,^a,^b Bin Zhang,^a,^c Cheng Wang,^b ^* Guo-Qiang Xu ^b and Yang Xie ^b

^aCollege of Material Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, People's Republic of China, ^bKey Laboratory of Polymer Functional Materials, College of Chemical Engineering and Material, Heilongjiang University, Harbin 150080, People's Republic of China, and ^cInstitute of Petrochemistry, HLJ Academy of Sciences, Harbin 150040, People's Republic of China
^*Correspondence e-mail: wangc_93@yahoo.com

(Received 8 December 2010; accepted 20 January 2011; online 26 January 2011)

The asymmetric unit of the title compound, [Ni(C₂H₈N₂)₃](C₈H₄O₅)·H₂O, contains one [Ni(en)₃]²⁺ cation (en is ethane-1,2-diamine), one 5-hydroxyisophthalate dianion and one water molecule. In the cation, the Ni²⁺ ion is coordinated by six N atoms from three ethylenediamine ligands in a distorted octahedral geometry. The complex ions and water molecules are linked by weak N—H⋯N/O and O—H⋯N/O hydrogen bonds into a three-demensional structure.

Related literature

For the construction of supramolecular networks, see: Colacio et al. (2002 ); Guilera & Steed (1999 ); Roesky & Andruh (2003 ). For the structures of compounds with 5-hydroxyisophthalic acid, see: Braverman & LaDuca (2007 ); Feller & Cheetham (2009 ); Li et al. (2005 ); Shao et al. (2009 ); Wang et al. (2007 ); Xu & Li (2004 ).

Experimental

Crystal data

[Ni(C₂H₈N₂)₃](C₈H₄O₅)·H₂O
M_r = 437.13
Monoclinic, P 2₁ /c
a = 8.208 (5) Å
b = 14.590 (5) Å
c = 16.581 (5) Å
β = 97.747 (5)°
V = 1967.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 K
0.10 × 0.08 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.906, T_max = 0.940
8306 measured reflections
3656 independent reflections
2997 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.00
3656 reflections
258 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N5	2.112 (2)
Ni1—N4	2.120 (2)
Ni1—N2	2.123 (2)
Ni1—N3	2.129 (2)
Ni1—N6	2.135 (2)
Ni1—N1	2.139 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H4⋯O2ⁱ	0.82	1.80	2.618 (2)	174
N5—H14⋯O4ⁱⁱ	0.90	2.09	2.958 (3)	161
N5—H13⋯O4ⁱⁱⁱ	0.90	2.38	3.238 (3)	159
N5—H13⋯O3ⁱⁱⁱ	0.90	2.50	3.266 (3)	143
N4—H19⋯O6^iv	0.90	2.30	3.173 (3)	162
N4—H20⋯O3ⁱⁱⁱ	0.90	2.11	2.924 (3)	150
N3—H31⋯O4ⁱⁱ	0.90	2.14	3.011 (3)	162
N3—H32⋯O2^v	0.90	2.41	3.214 (3)	148
N2—H27⋯O6^iv	0.90	2.27	3.097 (3)	152
N2—H28⋯O1^v	0.90	2.34	3.190 (3)	157
N6—H16⋯O5^vi	0.90	2.42	3.292 (3)	164
N6—H15⋯O1^v	0.90	2.49	3.285 (3)	148
O6—H5⋯O1^v	0.82 (2)	2.28 (2)	3.076 (4)	165 (3)
O6—H6⋯O1^vi	0.83 (2)	1.94 (2)	2.749 (3)	167 (3)
N1—H26⋯O3ⁱⁱⁱ	0.92 (2)	2.08 (2)	2.953 (3)	158 (2)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x+1, y, z; (v) -x+1, -y+1, -z+2; (vi) 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001449/hy2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001449/hy2388Isup2.hkl

checkCIF report

Comment top

There has been considerable interest in the crystal engineering of supramolecular architectures organized and sustained by means of coordinate covalent supramolecular contacts (such as hydrogen bonds), aurophilicity interactions, and so on (Colacio et al., 2002; Roesky & Andruh, 2003; Guilera & Steed, 1999). As a multidentate ligand, 5-hydroxyisophthalic acid has two rigid carboxyl groups but also one exible hydroxyl group. Therefore, 5-hydroxyisophthalic acid has been widely reported as a good candidate not only in the construction of various coordination polymers but also in the construction of supramolecular networks (Braverman & LaDuca, 2007; Feller & Cheetham, 2009; Li et al., 2005; Shao et al., 2009; Wang et al., 2007; Xu & Li, 2004).

The molecular structure of the title compound is illustrated in Fig. 1, and selected geometric parameters are listed in Table 1. The asymmetric unit of the title compound, [Ni(C₂H₈N₂)₃] [C₈H₄O₅]. H₂O, contains one [Ni(en)₃]²⁺ cation, one 5-hydroxyisophthalatedianion and one water molecules. In the title compound, the Ni²⁺ ion is coordinated by six N atoms from three ethylenediamine ligands in a distorted octahedral geometry. Note that a three-dimensional supramolecular hydrogen-bonding network is observed in the crystal structure of the title compound; details are given in Table 2.

Related literature top

For the construction of supramolecular networks, see: Colacio et al. (2002); Guilera & Steed (1999); Roesky & Andruh (2003). For the structures of compounds with 5-hydroxyisophthalic acid, see: Braverman & LaDuca (2007); Feller & Cheetham (2009); Li et al. (2005); Shao et al. (2009); Wang et al. (2007); Xu & Li (2004).

Experimental top

All chemicals were purchased from commercial sources and used without further purification. A mixture of nickel nitrate (Ni(NO₃)₂. 3H₂O (0.5 mmol), 5-hydroxyisophthalic acid (0.5 mmol) and ethylenediamine (0.1 mL) were dissolved in methanol (20 mL). The reaction mixture was stirred for 2 h at 313 K. The filtrate was kept at room temperature and brown block like single crystals were obtained after 3 months.

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of [Ni(C₂H₈N₂)₃] [C₈H₄O₅]. H₂O, with the atom labeling, showing displacement at the 30% ellipsoids probability level.
	Fig. 2. View of three-dimensional supramolecule framework of [Ni(C₂H₈N₂)₃] [C₈H₄O₅]. H₂O, with hydrogen bonds indicated by dashed lines.

Tris(ethane-1,2-diamine-κ²N,N')nickel(II) 5-hydroxyisophthalate monohydrate top

Crystal data top

[Ni(C₂H₈N₂)₃](C₈H₄O₅)·H₂O	F(000) = 928
M_r = 437.13	D_x = 1.476 Mg m⁻³ D_m = 1.476 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3656 reflections
a = 8.208 (5) Å	θ = 2.0–51.0°
b = 14.590 (5) Å	µ = 1.03 mm⁻¹
c = 16.581 (5) Å	T = 293 K
β = 97.747 (5)°	Block, brown
V = 1967.5 (15) Å³	0.10 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.906, T_max = 0.940	k = −16→17
8306 measured reflections	l = −20→9

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) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0592P)² + 0.2444P] where P = (F_o² + 2F_c²)/3
3656 reflections	(Δ/σ)_max = 0.004
258 parameters	Δρ_max = 0.45 e Å⁻³
4 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ni(C₂H₈N₂)₃](C₈H₄O₅)·H₂O	V = 1967.5 (15) Å³
M_r = 437.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.208 (5) Å	µ = 1.03 mm⁻¹
b = 14.590 (5) Å	T = 293 K
c = 16.581 (5) Å	0.10 × 0.08 × 0.06 mm
β = 97.747 (5)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3656 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2997 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.940	R_int = 0.026
8306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	4 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.45 e Å⁻³
3656 reflections	Δρ_min = −0.39 e Å⁻³
258 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
Ni1	0.91637 (3)	0.259626 (17)	0.974252 (16)	0.02383 (11)
O5	0.4795 (2)	1.20853 (10)	0.77712 (10)	0.0387 (4)
H4	0.5319	1.2412	0.7497	0.058*
C4	1.2188 (3)	0.3041 (2)	1.08329 (16)	0.0453 (6)
H17	1.1993	0.3693	1.0888	0.054*
H18	1.3343	0.2922	1.1010	0.054*
C9	0.4722 (3)	0.96063 (13)	0.79873 (13)	0.0247 (5)
O2	0.3689 (2)	0.81120 (11)	0.81877 (12)	0.0564 (6)
O3	0.8221 (2)	0.88664 (12)	0.64932 (12)	0.0527 (5)
O4	0.8811 (2)	1.03211 (12)	0.62789 (11)	0.0469 (5)
N5	0.8745 (2)	0.40180 (13)	0.95883 (12)	0.0338 (4)
H14	0.8949	0.4308	1.0071	0.041*
H13	0.9411	0.4252	0.9251	0.041*
C13	0.5152 (3)	1.11865 (13)	0.76445 (13)	0.0263 (5)
C11	0.6694 (2)	0.99956 (13)	0.70870 (12)	0.0232 (4)
O1	0.3348 (3)	0.91643 (12)	0.90927 (12)	0.0614 (6)
N4	1.1751 (2)	0.27597 (14)	0.99752 (13)	0.0352 (5)
H19	1.2254	0.2228	0.9885	0.042*
H20	1.2080	0.3189	0.9642	0.042*
N3	0.9414 (3)	0.26683 (14)	1.10360 (12)	0.0369 (5)
H31	0.9101	0.3224	1.1193	0.044*
H32	0.8776	0.2242	1.1230	0.044*
C8	0.8013 (3)	0.97061 (15)	0.65782 (13)	0.0300 (5)
C10	0.5897 (3)	0.93413 (14)	0.74970 (13)	0.0254 (5)
H2	0.6146	0.8724	0.7446	0.030*
C12	0.6296 (3)	1.09163 (13)	0.71495 (12)	0.0248 (4)
H3	0.6800	1.1353	0.6858	0.030*
C14	0.4373 (3)	1.05317 (14)	0.80625 (13)	0.0283 (5)
H1	0.3609	1.0714	0.8397	0.034*
N2	0.9402 (2)	0.11470 (13)	0.97466 (11)	0.0359 (5)
H27	1.0404	0.0985	0.9995	0.043*
H28	0.8642	0.0894	1.0021	0.043*
N1	0.9271 (3)	0.24104 (13)	0.84709 (13)	0.0346 (5)
N6	0.6543 (3)	0.25611 (13)	0.96287 (14)	0.0384 (5)
H16	0.6125	0.2314	0.9148	0.046*
H15	0.6214	0.2221	1.0030	0.046*
C7	0.3851 (3)	0.89121 (15)	0.84474 (15)	0.0338 (5)
C1	0.9958 (3)	0.14870 (17)	0.83782 (15)	0.0386 (6)
H21	1.1139	0.1497	0.8540	0.046*
H24	0.9747	0.1298	0.7813	0.046*
C2	0.9176 (3)	0.08176 (16)	0.89022 (15)	0.0436 (6)
H22	0.8012	0.0761	0.8707	0.052*
H23	0.9679	0.0219	0.8875	0.052*
C5	0.5970 (3)	0.35214 (19)	0.96839 (17)	0.0465 (7)
H11	0.6052	0.3705	1.0250	0.056*
H10	0.4828	0.3569	0.9445	0.056*
C6	0.7013 (3)	0.41394 (18)	0.92398 (18)	0.0464 (7)
H12	0.6869	0.3987	0.8665	0.056*
H9	0.6686	0.4773	0.9296	0.056*
C3	1.1144 (3)	0.25055 (18)	1.13507 (16)	0.0436 (6)
H30	1.1393	0.1857	1.1327	0.052*
H29	1.1369	0.2704	1.1913	0.052*
O6	0.3136 (3)	0.07283 (15)	0.99974 (13)	0.0559 (5)
H5	0.399 (3)	0.074 (2)	1.0317 (17)	0.067*
H6	0.335 (4)	0.0285 (17)	0.9720 (17)	0.067*
H26	1.001 (3)	0.2840 (15)	0.8337 (15)	0.041 (7)*
H25	0.827 (3)	0.2482 (17)	0.8153 (16)	0.046 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02321 (18)	0.02431 (16)	0.02524 (17)	−0.00172 (10)	0.00789 (12)	0.00261 (10)
O5	0.0551 (11)	0.0185 (7)	0.0477 (10)	0.0084 (7)	0.0258 (9)	0.0027 (7)
C4	0.0298 (14)	0.0588 (17)	0.0457 (15)	−0.0068 (12)	−0.0003 (12)	−0.0092 (13)
C9	0.0259 (11)	0.0224 (10)	0.0270 (11)	−0.0007 (8)	0.0086 (9)	−0.0007 (8)
O2	0.0734 (14)	0.0239 (9)	0.0829 (14)	−0.0119 (8)	0.0509 (12)	−0.0092 (9)
O3	0.0599 (12)	0.0319 (9)	0.0750 (13)	0.0058 (8)	0.0414 (11)	−0.0119 (9)
O4	0.0528 (11)	0.0409 (10)	0.0549 (11)	0.0008 (8)	0.0363 (9)	0.0066 (8)
N5	0.0342 (11)	0.0324 (10)	0.0368 (11)	−0.0025 (8)	0.0123 (9)	0.0024 (8)
C13	0.0324 (12)	0.0182 (10)	0.0293 (11)	0.0053 (8)	0.0079 (9)	0.0007 (8)
C11	0.0242 (11)	0.0236 (10)	0.0226 (10)	0.0003 (8)	0.0058 (9)	−0.0014 (8)
O1	0.1002 (16)	0.0370 (10)	0.0593 (13)	−0.0193 (10)	0.0558 (12)	−0.0076 (8)
N4	0.0284 (11)	0.0381 (11)	0.0407 (12)	−0.0017 (8)	0.0106 (9)	0.0031 (9)
N3	0.0388 (12)	0.0384 (11)	0.0358 (11)	−0.0020 (9)	0.0136 (10)	0.0022 (8)
C8	0.0323 (12)	0.0306 (12)	0.0291 (12)	0.0021 (9)	0.0116 (10)	−0.0044 (9)
C10	0.0318 (12)	0.0174 (10)	0.0280 (11)	0.0004 (8)	0.0075 (9)	−0.0021 (8)
C12	0.0301 (11)	0.0200 (10)	0.0258 (11)	−0.0008 (8)	0.0092 (9)	0.0030 (8)
C14	0.0308 (12)	0.0258 (11)	0.0314 (12)	0.0034 (9)	0.0154 (10)	−0.0008 (9)
N2	0.0401 (12)	0.0328 (10)	0.0352 (11)	−0.0043 (9)	0.0064 (9)	0.0054 (8)
N1	0.0383 (13)	0.0343 (11)	0.0322 (11)	−0.0027 (9)	0.0086 (10)	0.0030 (8)
N6	0.0320 (12)	0.0428 (12)	0.0414 (12)	−0.0073 (8)	0.0088 (10)	0.0039 (9)
C7	0.0383 (13)	0.0235 (11)	0.0427 (14)	−0.0020 (9)	0.0174 (11)	0.0015 (9)
C1	0.0428 (14)	0.0403 (13)	0.0333 (13)	0.0041 (11)	0.0077 (11)	−0.0063 (10)
C2	0.0599 (17)	0.0281 (12)	0.0408 (14)	−0.0025 (11)	−0.0001 (13)	−0.0019 (10)
C5	0.0266 (13)	0.0508 (16)	0.0636 (18)	0.0047 (11)	0.0113 (13)	0.0016 (13)
C6	0.0364 (14)	0.0396 (14)	0.0620 (18)	0.0084 (11)	0.0016 (13)	0.0115 (12)
C3	0.0438 (16)	0.0565 (17)	0.0294 (13)	0.0077 (12)	0.0016 (12)	−0.0015 (11)
O6	0.0534 (13)	0.0568 (13)	0.0561 (14)	0.0171 (10)	0.0023 (10)	−0.0102 (10)

Geometric parameters (Å, º) top

Ni1—N5	2.112 (2)	N3—C3	1.464 (4)
Ni1—N4	2.120 (2)	N3—H31	0.9000
Ni1—N2	2.123 (2)	N3—H32	0.9000
Ni1—N3	2.129 (2)	C10—H2	0.9300
Ni1—N6	2.135 (2)	C12—H3	0.9300
Ni1—N1	2.139 (2)	C14—H1	0.9300
O5—C13	1.366 (2)	N2—C2	1.468 (3)
O5—H4	0.8200	N2—H27	0.9000
C4—N4	1.477 (3)	N2—H28	0.9000
C4—C3	1.510 (4)	N1—C1	1.476 (3)
C4—H17	0.9700	N1—H26	0.922 (17)
C4—H18	0.9700	N1—H25	0.922 (18)
C9—C14	1.389 (3)	N6—C5	1.485 (3)
C9—C10	1.397 (3)	N6—H16	0.9000
C9—C7	1.505 (3)	N6—H15	0.9000
O2—C7	1.245 (3)	C1—C2	1.507 (3)
O3—C8	1.248 (3)	C1—H21	0.9700
O4—C8	1.252 (3)	C1—H24	0.9700
N5—C6	1.472 (3)	C2—H22	0.9700
N5—H14	0.9000	C2—H23	0.9700
N5—H13	0.9000	C5—C6	1.502 (4)
C13—C12	1.385 (3)	C5—H11	0.9700
C13—C14	1.386 (3)	C5—H10	0.9700
C11—C10	1.386 (3)	C6—H12	0.9700
C11—C12	1.390 (3)	C6—H9	0.9700
C11—C8	1.520 (3)	C3—H30	0.9700
O1—C7	1.253 (3)	C3—H29	0.9700
N4—H19	0.9000	O6—H5	0.818 (18)
N4—H20	0.9000	O6—H6	0.826 (17)

N5—Ni1—N4	93.10 (8)	C11—C12—H3	119.9
N5—Ni1—N2	172.57 (8)	C13—C14—C9	120.70 (18)
N4—Ni1—N2	91.25 (8)	C13—C14—H1	119.6
N5—Ni1—N3	93.76 (8)	C9—C14—H1	119.6
N4—Ni1—N3	81.53 (8)	C2—N2—Ni1	108.85 (14)
N2—Ni1—N3	92.84 (7)	C2—N2—H27	109.9
N5—Ni1—N6	82.39 (7)	Ni1—N2—H27	109.9
N4—Ni1—N6	172.57 (8)	C2—N2—H28	109.9
N2—Ni1—N6	93.89 (8)	Ni1—N2—H28	109.9
N3—Ni1—N6	92.85 (8)	H27—N2—H28	108.3
N5—Ni1—N1	91.88 (8)	C1—N1—Ni1	106.58 (15)
N4—Ni1—N1	91.15 (8)	C1—N1—H26	108.8 (17)
N2—Ni1—N1	82.00 (7)	Ni1—N1—H26	105.5 (16)
N3—Ni1—N1	170.99 (8)	C1—N1—H25	111.6 (16)
N6—Ni1—N1	94.87 (9)	Ni1—N1—H25	113.4 (19)
C13—O5—H4	109.5	H26—N1—H25	111 (2)
N4—C4—C3	108.7 (2)	C5—N6—Ni1	107.19 (14)
N4—C4—H17	109.9	C5—N6—H16	110.3
C3—C4—H17	109.9	Ni1—N6—H16	110.3
N4—C4—H18	109.9	C5—N6—H15	110.3
C3—C4—H18	109.9	Ni1—N6—H15	110.3
H17—C4—H18	108.3	H16—N6—H15	108.5
C14—C9—C10	119.18 (18)	O2—C7—O1	122.6 (2)
C14—C9—C7	119.40 (18)	O2—C7—C9	119.42 (19)
C10—C9—C7	121.40 (18)	O1—C7—C9	118.0 (2)
C6—N5—Ni1	107.36 (14)	N1—C1—C2	109.4 (2)
C6—N5—H14	110.2	N1—C1—H21	109.8
Ni1—N5—H14	110.2	C2—C1—H21	109.8
C6—N5—H13	110.2	N1—C1—H24	109.8
Ni1—N5—H13	110.2	C2—C1—H24	109.8
H14—N5—H13	108.5	H21—C1—H24	108.2
O5—C13—C12	122.75 (18)	N2—C2—C1	109.18 (19)
O5—C13—C14	117.49 (18)	N2—C2—H22	109.8
C12—C13—C14	119.70 (18)	C1—C2—H22	109.8
C10—C11—C12	119.87 (18)	N2—C2—H23	109.8
C10—C11—C8	119.97 (18)	C1—C2—H23	109.8
C12—C11—C8	120.15 (18)	H22—C2—H23	108.3
C4—N4—Ni1	108.26 (14)	N6—C5—C6	109.3 (2)
C4—N4—H19	110.0	N6—C5—H11	109.8
Ni1—N4—H19	110.0	C6—C5—H11	109.8
C4—N4—H20	110.0	N6—C5—H10	109.8
Ni1—N4—H20	110.0	C6—C5—H10	109.8
H19—N4—H20	108.4	H11—C5—H10	108.3
C3—N3—Ni1	107.96 (15)	N5—C6—C5	108.6 (2)
C3—N3—H31	110.1	N5—C6—H12	110.0
Ni1—N3—H31	110.1	C5—C6—H12	110.0
C3—N3—H32	110.1	N5—C6—H9	110.0
Ni1—N3—H32	110.1	C5—C6—H9	110.0
H31—N3—H32	108.4	H12—C6—H9	108.3
O3—C8—O4	124.9 (2)	N3—C3—C4	108.1 (2)
O3—C8—C11	117.01 (19)	N3—C3—H30	110.1
O4—C8—C11	118.07 (19)	C4—C3—H30	110.1
C11—C10—C9	120.22 (18)	N3—C3—H29	110.1
C11—C10—H2	119.9	C4—C3—H29	110.1
C9—C10—H2	119.9	H30—C3—H29	108.4
C13—C12—C11	120.28 (18)	H5—O6—H6	99 (3)
C13—C12—H3	119.9

N4—Ni1—N5—C6	168.22 (16)	C10—C9—C14—C13	1.4 (3)
N2—Ni1—N5—C6	42.5 (6)	C7—C9—C14—C13	−179.8 (2)
N3—Ni1—N5—C6	−110.08 (16)	N5—Ni1—N2—C2	23.7 (6)
N6—Ni1—N5—C6	−17.70 (16)	N4—Ni1—N2—C2	−102.10 (16)
N1—Ni1—N5—C6	76.96 (16)	N3—Ni1—N2—C2	176.32 (16)
C3—C4—N4—Ni1	40.3 (2)	N6—Ni1—N2—C2	83.27 (16)
N5—Ni1—N4—C4	80.33 (17)	N1—Ni1—N2—C2	−11.11 (16)
N2—Ni1—N4—C4	−105.70 (17)	N5—Ni1—N1—C1	166.69 (16)
N3—Ni1—N4—C4	−13.01 (16)	N4—Ni1—N1—C1	73.56 (16)
N6—Ni1—N4—C4	28.1 (7)	N2—Ni1—N1—C1	−17.54 (16)
N1—Ni1—N4—C4	172.28 (17)	N3—Ni1—N1—C1	38.0 (6)
N5—Ni1—N3—C3	−109.45 (16)	N6—Ni1—N1—C1	−110.79 (16)
N4—Ni1—N3—C3	−16.88 (15)	N5—Ni1—N6—C5	−11.55 (16)
N2—Ni1—N3—C3	73.96 (16)	N4—Ni1—N6—C5	41.3 (7)
N6—Ni1—N3—C3	168.00 (16)	N2—Ni1—N6—C5	174.91 (16)
N1—Ni1—N3—C3	19.1 (6)	N3—Ni1—N6—C5	81.87 (17)
C10—C11—C8—O3	6.3 (3)	N1—Ni1—N6—C5	−102.80 (17)
C12—C11—C8—O3	−174.4 (2)	C14—C9—C7—O2	155.0 (2)
C10—C11—C8—O4	−173.5 (2)	C10—C9—C7—O2	−26.2 (4)
C12—C11—C8—O4	5.8 (3)	C14—C9—C7—O1	−26.6 (4)
C12—C11—C10—C9	−1.4 (3)	C10—C9—C7—O1	152.2 (2)
C8—C11—C10—C9	177.87 (19)	Ni1—N1—C1—C2	43.2 (2)
C14—C9—C10—C11	−0.5 (3)	Ni1—N2—C2—C1	37.7 (2)
C7—C9—C10—C11	−179.3 (2)	N1—C1—C2—N2	−55.4 (3)
O5—C13—C12—C11	175.5 (2)	Ni1—N6—C5—C6	38.8 (2)
C14—C13—C12—C11	−1.6 (3)	Ni1—N5—C6—C5	44.1 (2)
C10—C11—C12—C13	2.5 (3)	N6—C5—C6—N5	−56.6 (3)
C8—C11—C12—C13	−176.8 (2)	Ni1—N3—C3—C4	43.4 (2)
O5—C13—C14—C9	−177.6 (2)	N4—C4—C3—N3	−56.7 (3)
C12—C13—C14—C9	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H4···O2ⁱ	0.82	1.80	2.618 (2)	174
N5—H14···O4ⁱⁱ	0.90	2.09	2.958 (3)	161
N5—H13···O4ⁱⁱⁱ	0.90	2.38	3.238 (3)	159
N5—H13···O3ⁱⁱⁱ	0.90	2.50	3.266 (3)	143
N4—H19···O6^iv	0.90	2.30	3.173 (3)	162
N4—H20···O3ⁱⁱⁱ	0.90	2.11	2.924 (3)	150
N3—H31···O4ⁱⁱ	0.90	2.14	3.011 (3)	162
N3—H32···O2^v	0.90	2.41	3.214 (3)	148
N2—H27···O6^iv	0.90	2.27	3.097 (3)	152
N2—H28···O1^v	0.90	2.34	3.190 (3)	157
N6—H16···O5^vi	0.90	2.42	3.292 (3)	164
N6—H15···O1^v	0.90	2.49	3.285 (3)	148
O6—H5···O1^v	0.82 (2)	2.28 (2)	3.076 (4)	165 (3)
O6—H6···O1^vi	0.83 (2)	1.94 (2)	2.749 (3)	167 (3)
N1—H26···O3ⁱⁱⁱ	0.92 (2)	2.08 (2)	2.953 (3)	158 (2)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂H₈N₂)₃](C₈H₄O₅)·H₂O
M_r	437.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.208 (5), 14.590 (5), 16.581 (5)
β (°)	97.747 (5)
V (Å³)	1967.5 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.10 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.906, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	8306, 3656, 2997
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.00
No. of reflections	3656
No. of parameters	258
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

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

Selected bond lengths (Å) top

Ni1—N5	2.112 (2)	Ni1—N3	2.129 (2)
Ni1—N4	2.120 (2)	Ni1—N6	2.135 (2)
Ni1—N2	2.123 (2)	Ni1—N1	2.139 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H4···O2ⁱ	0.82	1.80	2.618 (2)	174
N5—H14···O4ⁱⁱ	0.90	2.09	2.958 (3)	161
N5—H13···O4ⁱⁱⁱ	0.90	2.38	3.238 (3)	159
N5—H13···O3ⁱⁱⁱ	0.90	2.50	3.266 (3)	143
N4—H19···O6^iv	0.90	2.30	3.173 (3)	162
N4—H20···O3ⁱⁱⁱ	0.90	2.11	2.924 (3)	150
N3—H31···O4ⁱⁱ	0.90	2.14	3.011 (3)	162
N3—H32···O2^v	0.90	2.41	3.214 (3)	148
N2—H27···O6^iv	0.90	2.27	3.097 (3)	152
N2—H28···O1^v	0.90	2.34	3.190 (3)	157
N6—H16···O5^vi	0.90	2.42	3.292 (3)	164
N6—H15···O1^v	0.90	2.49	3.285 (3)	148
O6—H5···O1^v	0.818 (18)	2.277 (19)	3.076 (4)	165 (3)
O6—H6···O1^vi	0.826 (17)	1.938 (19)	2.749 (3)	167 (3)
N1—H26···O3ⁱⁱⁱ	0.922 (17)	2.076 (18)	2.953 (3)	158 (2)

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

Acknowledgements

The present study has been supported in part by the Abroad Person with Ability Foundation of Heilongjiang Province (Nos. 11551339, 2010td03), the NSFC (No. 20872030), the China Postdoctoral Foundation and the Elitist Foundation of Heilongjiang University (No. Hdtd2010-11).

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