(5-Amino­isophthalato-κN)triaqua­(1,10-phenanthroline-κ2N,N′)nickel(II) trihydrate

Huang, H.; Zhang, K.-L.; Ng, S.W.

doi:10.1107/S1600536811008919

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m444-m445

doi:10.1107/S1600536811008919

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(5-Aminoisophthalato-κN)triaqua(1,10-phenanthroline-κ²N,N′)nickel(II) trihydrate

Han Huang,^a Kou-Lin Zhang ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 February 2011; accepted 9 March 2011; online 15 March 2011)

The Ni^II atom in the title compound, [Ni(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O, is six-coordinated in an NiN₃O₃ octahedral geometry. The triply water-coordinated Ni^II atom is chelated by the phenantroline ligand and is additionally coordinated by the amino group of the 5-aminoisophtalate anion. The anion, the coordinated and the uncoordinated water molecules interact through an extensive O—H⋯O and N—H⋯O hydrogen-bonding network, generating a three-dimensional cage-like network.

Related literature

For the isotypic Co^II analog, see: Zhang et al. (2010 ).

Experimental

Crystal data

[Ni(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O
M_r = 526.14
Monoclinic, P 2₁ /n
a = 10.1039 (10) Å
b = 13.9448 (14) Å
c = 16.4237 (16) Å
β = 95.522 (1)°
V = 2303.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 295 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.892, T_max = 0.915
20080 measured reflections
5258 independent reflections
3702 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.081
S = 0.89
5258 reflections
363 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1w	2.0408 (16)
Ni1—N2	2.0800 (16)
Ni1—O2w	2.0797 (14)
Ni1—N3	2.0883 (16)
Ni1—O3w	2.0965 (15)
Ni1—N1	2.1409 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O6wⁱ	0.84 (1)	1.91 (1)	2.747 (2)	177 (3)
O1w—H1w2⋯O2ⁱⁱ	0.84 (1)	1.82 (1)	2.654 (2)	180 (2)
O2w—H2w1⋯O5wⁱ	0.85 (1)	1.94 (1)	2.781 (2)	173 (3)
O2w—H2w2⋯O4ⁱⁱⁱ	0.85 (1)	1.98 (1)	2.832 (2)	178 (3)
O3w—H3w1⋯O5w^iv	0.84 (1)	2.16 (2)	2.914 (3)	148 (3)
O3w—H3w2⋯O3ⁱⁱ	0.85 (1)	1.88 (1)	2.721 (2)	173 (3)
O4w—H4w1⋯O6w^v	0.85 (1)	1.97 (1)	2.817 (3)	171 (3)
O4w—H4w2⋯O2^iv	0.85 (1)	2.16 (2)	2.915 (3)	149 (3)
O5w—H5w1⋯O1	0.85 (1)	1.90 (1)	2.726 (3)	163 (3)
O5w—H5w2⋯O3^vi	0.84 (1)	1.91 (1)	2.716 (2)	159 (3)
O6w—H6w1⋯O1	0.85 (1)	1.83 (1)	2.678 (2)	177 (3)
O6w—H6w2⋯O4ⁱⁱⁱ	0.85 (1)	1.95 (1)	2.791 (2)	176 (3)
N1—H1⋯O4w	0.85 (1)	2.08 (1)	2.928 (3)	173 (2)
N1—H2⋯O4ⁱⁱⁱ	0.85 (1)	2.30 (1)	3.116 (2)	162 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; method used to solve structure: atomic coordinates taken from an isotypic structure (Zhang et al., 2010); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008919/wm2464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008919/wm2464Isup2.hkl

checkCIF report

Comment top

We reported the structure of [Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]^.3H₂O], whose 5-aminoisophthlate dianion binds only through the neutral amino donor site. The coordinated water molecules comprise the fac points of the NiN₃O₃ octahedron (Zhang et al., 2010). The nickel analog (Scheme I) is isotypic. The dianion, the coordinated and the lattice water molecules interact through hydrogen bonds (Table 1) to furnish a tightly-held, three-dimensional network. Pairs of phenanthroline units show π···π interactions about a center-of-inversion at a distance of ca 3.5 Å.

Related literature top

For the isotypic Co^II analog, see: Zhang et al. (2010).

Experimental top

Nickel nitrate hexahydrate (0.048 g, 0.165 mmol) dissolved in water (5 ml) was added to a mixture of 5-aminoisophthalic acid (0.030 g, 0.165 mmol) and sodium hydroxide (0.013 g, 0.330 mmol) dissolved in water (5 ml). To this solution was added 1,10-phenanthroline (0.033 g, 0.165 mmol) dissolved in methanol (10 ml). The mixture was filtered and set aside for the growth of green crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: atomic coordinates taken from an isotypic structure (Zhang et al., 2010); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular entities of (I) with atom labelling and displacement parameters at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius.

(5-Aminoisophthalato-κN)triaqua(1,10-phenanthroline- κ²N,N')nickel(II) trihydrate top

Crystal data top

[Ni(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O	F(000) = 1096
M_r = 526.14	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5121 reflections
a = 10.1039 (10) Å	θ = 2.3–26.3°
b = 13.9448 (14) Å	µ = 0.90 mm⁻¹
c = 16.4237 (16) Å	T = 295 K
β = 95.522 (1)°	Block, green
V = 2303.3 (4) Å³	0.13 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5258 independent reflections
Radiation source: fine-focus sealed tube	3702 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.892, T_max = 0.915	k = −18→18
20080 measured reflections	l = −21→20

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0347P)²] where P = (F_o² + 2F_c²)/3
5258 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.35 e Å⁻³
14 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Ni(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O	V = 2303.3 (4) Å³
M_r = 526.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1039 (10) Å	µ = 0.90 mm⁻¹
b = 13.9448 (14) Å	T = 295 K
c = 16.4237 (16) Å	0.13 × 0.12 × 0.10 mm
β = 95.522 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	5258 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3702 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.915	R_int = 0.092
20080 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	14 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.35 e Å⁻³
5258 reflections	Δρ_min = −0.55 e Å⁻³
363 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.74294 (2)	0.686043 (16)	0.465623 (15)	0.02405 (8)
O1	1.15737 (15)	0.53335 (11)	0.26472 (11)	0.0506 (5)
O2	1.22244 (15)	0.64153 (11)	0.18022 (11)	0.0484 (4)
O3	0.91901 (14)	0.91569 (10)	0.09761 (9)	0.0368 (4)
O4	0.72199 (14)	0.92528 (10)	0.14342 (10)	0.0413 (4)
O1w	0.76412 (16)	0.70612 (11)	0.58928 (10)	0.0360 (4)
H1w1	0.8275 (18)	0.6793 (16)	0.6169 (14)	0.054 (8)*
H1w2	0.751 (2)	0.7541 (11)	0.6177 (12)	0.044 (7)*
O2w	0.79265 (16)	0.54505 (10)	0.49643 (10)	0.0331 (3)
H2w1	0.743 (2)	0.5271 (18)	0.5323 (12)	0.059 (9)*
H2w2	0.787 (3)	0.5091 (17)	0.4543 (11)	0.074 (10)*
O3w	0.53887 (15)	0.66633 (12)	0.47353 (11)	0.0370 (4)
H3w1	0.493 (3)	0.642 (2)	0.4334 (14)	0.097 (12)*
H3w2	0.507 (3)	0.6419 (18)	0.5148 (11)	0.071 (9)*
O4w	0.4426 (2)	0.71882 (19)	0.28820 (16)	0.0763 (7)
H4w1	0.449 (3)	0.7708 (14)	0.2618 (18)	0.090 (12)*
H4w2	0.403 (3)	0.681 (2)	0.2532 (18)	0.111 (16)*
O5w	1.36084 (19)	0.52842 (12)	0.38634 (12)	0.0482 (4)
H5w1	1.309 (2)	0.5233 (18)	0.3428 (10)	0.055 (9)*
H5w2	1.4241 (18)	0.4915 (16)	0.3787 (16)	0.061 (9)*
O6w	1.03103 (17)	0.37826 (11)	0.31434 (11)	0.0426 (4)
H6w1	1.069 (3)	0.4278 (14)	0.2974 (18)	0.088 (11)*
H6w2	0.9539 (14)	0.3894 (18)	0.3281 (16)	0.062 (9)*
N1	0.70709 (18)	0.64237 (12)	0.34047 (11)	0.0268 (4)
H1	0.6280 (12)	0.6600 (15)	0.3259 (14)	0.042 (7)*
H2	0.708 (2)	0.5815 (7)	0.3415 (14)	0.044 (7)*
N2	0.71486 (16)	0.83087 (11)	0.43901 (11)	0.0306 (4)
N3	0.93864 (16)	0.72811 (11)	0.45417 (11)	0.0282 (4)
C1	0.79789 (19)	0.67558 (13)	0.28500 (12)	0.0247 (4)
C2	0.91676 (19)	0.62745 (13)	0.27875 (12)	0.0266 (4)
H2A	0.9348	0.5716	0.3087	0.032*
C3	1.00920 (19)	0.66171 (13)	0.22835 (12)	0.0257 (4)
C4	0.98077 (19)	0.74537 (13)	0.18383 (13)	0.0265 (4)
H4	1.0420	0.7689	0.1501	0.032*
C5	0.86192 (19)	0.79422 (13)	0.18922 (12)	0.0248 (4)
C6	0.77066 (19)	0.75923 (13)	0.24048 (12)	0.0263 (4)
H6	0.6915	0.7919	0.2449	0.032*
C7	1.1392 (2)	0.60854 (14)	0.22376 (14)	0.0301 (5)
C8	0.83267 (19)	0.88458 (13)	0.14050 (13)	0.0260 (4)
C9	0.6034 (2)	0.88175 (16)	0.43450 (14)	0.0418 (6)
H9	0.5250	0.8512	0.4450	0.050*
C10	0.5988 (3)	0.97908 (17)	0.41470 (16)	0.0499 (7)
H10	0.5190	1.0125	0.4130	0.060*
C11	0.7119 (3)	1.02457 (16)	0.39797 (15)	0.0501 (7)
H11	0.7097	1.0895	0.3852	0.060*
C12	0.8322 (2)	0.97357 (15)	0.40000 (15)	0.0415 (6)
C13	0.8284 (2)	0.87628 (14)	0.42274 (13)	0.0302 (5)
C14	0.9557 (3)	1.01401 (18)	0.38102 (17)	0.0592 (8)
H14	0.9587	1.0781	0.3657	0.071*
C15	1.0675 (3)	0.96117 (19)	0.38490 (18)	0.0606 (8)
H15	1.1459	0.9889	0.3708	0.073*
C16	1.0679 (2)	0.86237 (17)	0.41062 (16)	0.0447 (6)
C17	0.9485 (2)	0.82052 (14)	0.42931 (13)	0.0309 (5)
C18	1.1817 (2)	0.80332 (19)	0.41870 (18)	0.0561 (7)
H18	1.2631	0.8269	0.4055	0.067*
C19	1.1720 (2)	0.71140 (19)	0.44591 (17)	0.0518 (7)
H19	1.2472	0.6727	0.4530	0.062*
C20	1.0490 (2)	0.67576 (16)	0.46297 (14)	0.0376 (5)
H20	1.0438	0.6129	0.4812	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02322 (14)	0.02102 (12)	0.02825 (15)	0.00025 (10)	0.00421 (10)	−0.00008 (11)
O1	0.0315 (9)	0.0409 (9)	0.0806 (13)	0.0094 (7)	0.0107 (9)	0.0334 (9)
O2	0.0349 (9)	0.0411 (9)	0.0730 (12)	0.0125 (7)	0.0248 (8)	0.0254 (9)
O3	0.0359 (8)	0.0326 (8)	0.0437 (10)	0.0020 (6)	0.0139 (7)	0.0150 (7)
O4	0.0363 (9)	0.0308 (8)	0.0594 (11)	0.0116 (7)	0.0170 (8)	0.0170 (7)
O1w	0.0397 (9)	0.0367 (9)	0.0307 (9)	0.0105 (7)	−0.0013 (8)	−0.0102 (7)
O2w	0.0453 (10)	0.0239 (7)	0.0302 (9)	−0.0001 (7)	0.0043 (8)	−0.0023 (7)
O3w	0.0277 (8)	0.0503 (10)	0.0339 (10)	−0.0067 (7)	0.0073 (8)	0.0004 (8)
O4w	0.0468 (12)	0.0806 (16)	0.0972 (19)	−0.0116 (12)	−0.0149 (12)	0.0407 (15)
O5w	0.0492 (12)	0.0439 (10)	0.0510 (12)	0.0107 (9)	0.0022 (10)	0.0044 (9)
O6w	0.0340 (9)	0.0325 (8)	0.0620 (12)	0.0006 (7)	0.0077 (9)	0.0046 (8)
N1	0.0275 (10)	0.0246 (9)	0.0289 (10)	−0.0008 (7)	0.0050 (8)	0.0054 (8)
N2	0.0292 (9)	0.0276 (9)	0.0351 (10)	0.0039 (7)	0.0040 (8)	0.0003 (7)
N3	0.0255 (9)	0.0250 (8)	0.0339 (10)	0.0011 (7)	0.0026 (8)	−0.0019 (7)
C1	0.0277 (10)	0.0246 (10)	0.0220 (10)	−0.0023 (8)	0.0035 (8)	0.0005 (8)
C2	0.0298 (11)	0.0225 (9)	0.0272 (12)	0.0005 (8)	0.0020 (9)	0.0038 (8)
C3	0.0247 (11)	0.0233 (9)	0.0291 (12)	0.0007 (8)	0.0023 (9)	0.0010 (8)
C4	0.0255 (10)	0.0250 (9)	0.0297 (11)	−0.0002 (8)	0.0062 (9)	0.0047 (8)
C5	0.0254 (10)	0.0220 (9)	0.0273 (11)	0.0002 (7)	0.0036 (9)	0.0016 (8)
C6	0.0251 (10)	0.0251 (10)	0.0294 (12)	0.0047 (8)	0.0069 (9)	0.0023 (8)
C7	0.0251 (11)	0.0248 (10)	0.0400 (13)	0.0003 (8)	0.0013 (10)	0.0046 (9)
C8	0.0274 (11)	0.0218 (9)	0.0293 (12)	0.0009 (8)	0.0052 (9)	0.0020 (8)
C9	0.0379 (13)	0.0374 (12)	0.0502 (16)	0.0104 (10)	0.0054 (11)	0.0036 (11)
C10	0.0548 (16)	0.0411 (13)	0.0532 (17)	0.0242 (12)	0.0026 (13)	0.0047 (12)
C11	0.0728 (19)	0.0283 (12)	0.0472 (16)	0.0087 (12)	−0.0040 (14)	0.0060 (11)
C12	0.0558 (15)	0.0263 (11)	0.0416 (15)	−0.0030 (10)	−0.0001 (12)	0.0076 (10)
C13	0.0370 (12)	0.0245 (10)	0.0287 (12)	−0.0019 (9)	0.0005 (10)	−0.0008 (9)
C14	0.070 (2)	0.0360 (13)	0.070 (2)	−0.0163 (13)	0.0022 (16)	0.0167 (13)
C15	0.0546 (17)	0.0536 (16)	0.074 (2)	−0.0244 (14)	0.0083 (15)	0.0153 (15)
C16	0.0361 (13)	0.0468 (14)	0.0511 (16)	−0.0122 (11)	0.0034 (12)	0.0046 (12)
C17	0.0296 (11)	0.0293 (10)	0.0336 (12)	−0.0043 (9)	0.0023 (9)	−0.0005 (9)
C18	0.0264 (13)	0.0691 (18)	0.074 (2)	−0.0113 (12)	0.0101 (13)	0.0005 (15)
C19	0.0266 (13)	0.0561 (16)	0.072 (2)	0.0056 (11)	0.0036 (13)	−0.0040 (14)
C20	0.0308 (12)	0.0355 (11)	0.0457 (14)	0.0054 (9)	0.0000 (11)	−0.0018 (10)

Geometric parameters (Å, º) top

Ni1—O1w	2.0408 (16)	C1—C2	1.388 (3)
Ni1—N2	2.0800 (16)	C2—C3	1.391 (3)
Ni1—O2w	2.0797 (14)	C2—H2A	0.9300
Ni1—N3	2.0883 (16)	C3—C4	1.392 (3)
Ni1—O3w	2.0965 (15)	C3—C7	1.516 (3)
Ni1—N1	2.1409 (18)	C4—C5	1.391 (3)
O1—C7	1.250 (2)	C4—H4	0.9300
O2—C7	1.244 (2)	C5—C6	1.395 (3)
O3—C8	1.250 (2)	C5—C8	1.507 (3)
O4—C8	1.259 (2)	C6—H6	0.9300
O1w—H1w1	0.84 (1)	C9—C10	1.395 (3)
O1w—H1w2	0.84 (1)	C9—H9	0.9300
O2w—H2w1	0.85 (1)	C10—C11	1.357 (3)
O2w—H2w2	0.85 (1)	C10—H10	0.9300
O3w—H3w1	0.84 (1)	C11—C12	1.406 (3)
O3w—H3w2	0.85 (1)	C11—H11	0.9300
O4w—H4w1	0.85 (1)	C12—C13	1.409 (3)
O4w—H4w2	0.85 (1)	C12—C14	1.431 (3)
O5w—H5w1	0.85 (1)	C13—C17	1.437 (3)
O5w—H5w2	0.84 (1)	C14—C15	1.346 (4)
O6w—H6w1	0.85 (1)	C14—H14	0.9300
O6w—H6w2	0.85 (1)	C15—C16	1.441 (3)
N1—C1	1.431 (2)	C15—H15	0.9300
N1—H1	0.85 (1)	C16—C17	1.401 (3)
N1—H2	0.85 (1)	C16—C18	1.410 (3)
N2—C9	1.327 (3)	C18—C19	1.364 (4)
N2—C13	1.359 (3)	C18—H18	0.9300
N3—C20	1.329 (2)	C19—C20	1.392 (3)
N3—C17	1.358 (2)	C19—H19	0.9300
C1—C6	1.390 (3)	C20—H20	0.9300

O1w—Ni1—N2	94.30 (7)	C5—C4—H4	119.6
O1w—Ni1—O2w	83.56 (6)	C4—C5—C6	119.46 (17)
N2—Ni1—O2w	173.68 (7)	C4—C5—C8	120.15 (17)
O1w—Ni1—N3	92.38 (7)	C6—C5—C8	120.39 (17)
N2—Ni1—N3	79.60 (6)	C1—C6—C5	120.14 (18)
O2w—Ni1—N3	94.52 (6)	C1—C6—H6	119.9
O1w—Ni1—O3w	88.05 (7)	C5—C6—H6	119.9
N2—Ni1—O3w	91.45 (6)	O2—C7—O1	123.19 (19)
O2w—Ni1—O3w	94.41 (6)	O2—C7—C3	118.99 (17)
N3—Ni1—O3w	171.05 (6)	O1—C7—C3	117.82 (19)
O1w—Ni1—N1	170.49 (6)	O3—C8—O4	122.37 (18)
N2—Ni1—N1	93.87 (7)	O3—C8—C5	118.53 (17)
O2w—Ni1—N1	88.81 (6)	O4—C8—C5	119.09 (17)
N3—Ni1—N1	93.88 (7)	N2—C9—C10	122.8 (2)
O3w—Ni1—N1	86.89 (7)	N2—C9—H9	118.6
Ni1—O1w—H1w1	118.7 (18)	C10—C9—H9	118.6
Ni1—O1w—H1w2	131.3 (16)	C11—C10—C9	119.5 (2)
H1w1—O1w—H1w2	102 (2)	C11—C10—H10	120.3
Ni1—O2w—H2w1	107.6 (18)	C9—C10—H10	120.3
Ni1—O2w—H2w2	111.2 (19)	C10—C11—C12	120.1 (2)
H2w1—O2w—H2w2	113 (3)	C10—C11—H11	120.0
Ni1—O3w—H3w1	119 (2)	C12—C11—H11	120.0
Ni1—O3w—H3w2	123.6 (19)	C11—C12—C13	116.6 (2)
H3w1—O3w—H3w2	104 (3)	C11—C12—C14	124.4 (2)
H4w1—O4w—H4w2	104 (3)	C13—C12—C14	118.9 (2)
H5w1—O5w—H5w2	104 (3)	N2—C13—C12	123.1 (2)
H6w1—O6w—H6w2	113 (3)	N2—C13—C17	117.12 (17)
C1—N1—Ni1	117.36 (13)	C12—C13—C17	119.8 (2)
C1—N1—H1	111.8 (16)	C15—C14—C12	121.3 (2)
Ni1—N1—H1	104.8 (16)	C15—C14—H14	119.3
C1—N1—H2	109.2 (16)	C12—C14—H14	119.3
Ni1—N1—H2	105.4 (16)	C14—C15—C16	121.1 (2)
H1—N1—H2	108 (2)	C14—C15—H15	119.5
C9—N2—C13	117.89 (18)	C16—C15—H15	119.5
C9—N2—Ni1	128.95 (15)	C17—C16—C18	116.6 (2)
C13—N2—Ni1	113.14 (13)	C17—C16—C15	119.0 (2)
C20—N3—C17	117.96 (18)	C18—C16—C15	124.4 (2)
C20—N3—Ni1	128.87 (14)	N3—C17—C16	123.43 (19)
C17—N3—Ni1	113.03 (13)	N3—C17—C13	116.75 (18)
C6—C1—C2	119.71 (18)	C16—C17—C13	119.82 (19)
C6—C1—N1	120.00 (17)	C19—C18—C16	119.7 (2)
C2—C1—N1	120.20 (17)	C19—C18—H18	120.1
C1—C2—C3	120.88 (18)	C16—C18—H18	120.1
C1—C2—H2A	119.6	C18—C19—C20	119.7 (2)
C3—C2—H2A	119.6	C18—C19—H19	120.1
C4—C3—C2	118.95 (18)	C20—C19—H19	120.1
C4—C3—C7	121.31 (18)	N3—C20—C19	122.5 (2)
C2—C3—C7	119.74 (17)	N3—C20—H20	118.7
C3—C4—C5	120.86 (18)	C19—C20—H20	118.7
C3—C4—H4	119.6

N2—Ni1—N1—C1	63.44 (14)	C4—C5—C8—O4	176.82 (19)
O2w—Ni1—N1—C1	−110.83 (14)	C6—C5—C8—O4	−3.6 (3)
N3—Ni1—N1—C1	−16.38 (14)	C13—N2—C9—C10	−0.6 (3)
O3w—Ni1—N1—C1	154.68 (14)	Ni1—N2—C9—C10	−179.05 (18)
O1w—Ni1—N2—C9	−85.7 (2)	N2—C9—C10—C11	1.0 (4)
N3—Ni1—N2—C9	−177.4 (2)	C9—C10—C11—C12	0.5 (4)
O3w—Ni1—N2—C9	2.4 (2)	C10—C11—C12—C13	−2.2 (4)
N1—Ni1—N2—C9	89.4 (2)	C10—C11—C12—C14	178.1 (2)
O1w—Ni1—N2—C13	95.80 (15)	C9—N2—C13—C12	−1.2 (3)
N3—Ni1—N2—C13	4.16 (14)	Ni1—N2—C13—C12	177.41 (17)
O3w—Ni1—N2—C13	−176.05 (15)	C9—N2—C13—C17	178.95 (19)
N1—Ni1—N2—C13	−89.08 (15)	Ni1—N2—C13—C17	−2.4 (2)
O1w—Ni1—N3—C20	85.17 (19)	C11—C12—C13—N2	2.6 (3)
N2—Ni1—N3—C20	179.1 (2)	C14—C12—C13—N2	−177.6 (2)
O2w—Ni1—N3—C20	1.45 (19)	C11—C12—C13—C17	−177.6 (2)
N1—Ni1—N3—C20	−87.66 (19)	C14—C12—C13—C17	2.2 (3)
O1w—Ni1—N3—C17	−99.33 (15)	C11—C12—C14—C15	179.4 (3)
N2—Ni1—N3—C17	−5.39 (14)	C13—C12—C14—C15	−0.3 (4)
O2w—Ni1—N3—C17	176.95 (15)	C12—C14—C15—C16	−1.8 (5)
N1—Ni1—N3—C17	87.83 (15)	C14—C15—C16—C17	2.0 (4)
Ni1—N1—C1—C6	−93.21 (19)	C14—C15—C16—C18	−177.9 (3)
Ni1—N1—C1—C2	83.2 (2)	C20—N3—C17—C16	1.7 (3)
C6—C1—C2—C3	−0.1 (3)	Ni1—N3—C17—C16	−174.38 (18)
N1—C1—C2—C3	−176.57 (17)	C20—N3—C17—C13	−178.14 (19)
C1—C2—C3—C4	−0.1 (3)	Ni1—N3—C17—C13	5.8 (2)
C1—C2—C3—C7	179.01 (18)	C18—C16—C17—N3	0.0 (4)
C2—C3—C4—C5	−0.1 (3)	C15—C16—C17—N3	−179.9 (2)
C7—C3—C4—C5	−179.23 (18)	C18—C16—C17—C13	179.8 (2)
C3—C4—C5—C6	0.6 (3)	C15—C16—C17—C13	−0.1 (4)
C3—C4—C5—C8	−179.89 (18)	N2—C13—C17—N3	−2.3 (3)
C2—C1—C6—C5	0.5 (3)	C12—C13—C17—N3	177.8 (2)
N1—C1—C6—C5	177.01 (17)	N2—C13—C17—C16	177.8 (2)
C4—C5—C6—C1	−0.8 (3)	C12—C13—C17—C16	−2.0 (3)
C8—C5—C6—C1	179.70 (18)	C17—C16—C18—C19	−1.9 (4)
C4—C3—C7—O2	1.1 (3)	C15—C16—C18—C19	178.0 (3)
C2—C3—C7—O2	−177.98 (19)	C16—C18—C19—C20	2.0 (4)
C4—C3—C7—O1	−179.3 (2)	C17—N3—C20—C19	−1.5 (3)
C2—C3—C7—O1	1.7 (3)	Ni1—N3—C20—C19	173.77 (18)
C4—C5—C8—O3	−2.2 (3)	C18—C19—C20—N3	−0.3 (4)
C6—C5—C8—O3	177.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O6wⁱ	0.84 (1)	1.91 (1)	2.747 (2)	177 (3)
O1w—H1w2···O2ⁱⁱ	0.84 (1)	1.82 (1)	2.654 (2)	180 (2)
O2w—H2w1···O5wⁱ	0.85 (1)	1.94 (1)	2.781 (2)	173 (3)
O2w—H2w2···O4ⁱⁱⁱ	0.85 (1)	1.98 (1)	2.832 (2)	178 (3)
O3w—H3w1···O5w^iv	0.84 (1)	2.16 (2)	2.914 (3)	148 (3)
O3w—H3w2···O3ⁱⁱ	0.85 (1)	1.88 (1)	2.721 (2)	173 (3)
O4w—H4w1···O6w^v	0.85 (1)	1.97 (1)	2.817 (3)	171 (3)
O4w—H4w2···O2^iv	0.85 (1)	2.16 (2)	2.915 (3)	149 (3)
O5w—H5w1···O1	0.85 (1)	1.90 (1)	2.726 (3)	163 (3)
O5w—H5w2···O3^vi	0.84 (1)	1.91 (1)	2.716 (2)	159 (3)
O6w—H6w1···O1	0.85 (1)	1.83 (1)	2.678 (2)	177 (3)
O6w—H6w2···O4ⁱⁱⁱ	0.85 (1)	1.95 (1)	2.791 (2)	176 (3)
N1—H1···O4w	0.85 (1)	2.08 (1)	2.928 (3)	173 (2)
N1—H2···O4ⁱⁱⁱ	0.85 (1)	2.30 (1)	3.116 (2)	162 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O
M_r	526.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.1039 (10), 13.9448 (14), 16.4237 (16)
β (°)	95.522 (1)
V (Å³)	2303.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.892, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	20080, 5258, 3702
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.081, 0.89
No. of reflections	5258
No. of parameters	363
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.55

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), atomic coordinates taken from an isotypic structure (Zhang et al., 2010), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni1—O1w	2.0408 (16)	Ni1—N3	2.0883 (16)
Ni1—N2	2.0800 (16)	Ni1—O3w	2.0965 (15)
Ni1—O2w	2.0797 (14)	Ni1—N1	2.1409 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O6wⁱ	0.84 (1)	1.91 (1)	2.747 (2)	177 (3)
O1w—H1w2···O2ⁱⁱ	0.84 (1)	1.82 (1)	2.654 (2)	180 (2)
O2w—H2w1···O5wⁱ	0.85 (1)	1.94 (1)	2.781 (2)	173 (3)
O2w—H2w2···O4ⁱⁱⁱ	0.85 (1)	1.98 (1)	2.832 (2)	178 (3)
O3w—H3w1···O5w^iv	0.84 (1)	2.16 (2)	2.914 (3)	148 (3)
O3w—H3w2···O3ⁱⁱ	0.85 (1)	1.88 (1)	2.721 (2)	173 (3)
O4w—H4w1···O6w^v	0.85 (1)	1.97 (1)	2.817 (3)	171 (3)
O4w—H4w2···O2^iv	0.85 (1)	2.16 (2)	2.915 (3)	149 (3)
O5w—H5w1···O1	0.85 (1)	1.90 (1)	2.726 (3)	163 (3)
O5w—H5w2···O3^vi	0.84 (1)	1.91 (1)	2.716 (2)	159 (3)
O6w—H6w1···O1	0.85 (1)	1.83 (1)	2.678 (2)	177 (3)
O6w—H6w2···O4ⁱⁱⁱ	0.85 (1)	1.95 (1)	2.791 (2)	176 (3)
N1—H1···O4w	0.85 (1)	2.08 (1)	2.928 (3)	173 (2)
N1—H2···O4ⁱⁱⁱ	0.85 (1)	2.30 (1)	3.116 (2)	162 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, Yangzhou University, and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Winsonsin, USA. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, K.-L., Diao, G.-W. & Ng, S. W. (2010). Acta Cryst. E66, m1421. Web of Science CSD CrossRef IUCr Journals Google Scholar

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