catena-Poly[[diaqua­(1,10-phenanthroline-κ2N,N′)nickel(II)]-μ-1H-benzimidazole-5,6-dicarboxyl­ato-κ2N3:O6]

Song, W.-D.; Wang, H.; Hu, S.-W.; Qin, P.-W.; Li, S.-J.

doi:10.1107/S1600536809019680

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m701

doi:10.1107/S1600536809019680

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catena-Poly[[diaqua(1,10-phenanthroline-κ²N,N′)nickel(II)]-μ-1H-benzimidazole-5,6-dicarboxylato-κ²N³:O⁶]

Wen-Dong Song,^a ^* Hao Wang,^a Shi-Wei Hu,^a Pei-Wen Qin ^a and Shi-Jie Li ^a

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 18 May 2009; accepted 24 May 2009; online 29 May 2009)

In the title complex, [Ni(C₉H₄N₂O₄)(C₁₂H₈N₂)(H₂O)₂]_n, the Ni^II atom is hexacoordinated by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxylate ligands, two N atoms from one 1,10-phenanthroline ligand and two water molecules. The flexible 1H-benzimidazole-5,6-dicarboxylate ligands link the Ni^II centres, forming an infinite zigzag chain parallel to [001]. The crystal packing is governed by intermolecular hydrogen-bonding interactions of the O—H⋯O, N—H⋯O and C—H⋯O types.

Related literature

For background to 1H-benzoimidazole-5,6-dicarboxylate complexes, see: Lo et al. (2007 ); Yao et al. (2008 ); Gao et al. (2008 ). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999 ).

Experimental

Crystal data

[Ni(C₉H₄N₂O₄)(C₁₂H₈N₂)(H₂O)₂]
M_r = 479.09
Monoclinic, P 2₁ /c
a = 10.021 (2) Å
b = 16.980 (3) Å
c = 15.327 (5) Å
β = 129.09 (2)°
V = 2024.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 293 K
0.31 × 0.26 × 0.22 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.746, T_max = 0.809
15765 measured reflections
3639 independent reflections
3195 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.091
S = 1.09
3639 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1ⁱ	0.84	1.90	2.710 (2)	163
O1W—H2W⋯O4ⁱⁱ	0.84	1.76	2.584 (2)	165
O2W—H3W⋯O1ⁱ	0.84	1.87	2.703 (2)	169
O2W—H4W⋯O1ⁱⁱ	0.84	2.11	2.932 (2)	165
N2—H2⋯O2ⁱⁱⁱ	0.86	2.00	2.739 (2)	144
N2—H2⋯O1ⁱⁱⁱ	0.86	2.54	3.355 (2)	159
C10—H10⋯O2ⁱⁱ	0.93	2.56	3.346 (8)	143
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019680/im2119sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019680/im2119Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 1H-benzimidazole-5,6-dicarboxylate complexes, it has been found that 1H-benzimidazole-5,6-dicarboxylic acid can function as a multidentate ligand (Lo et al., 2007; Yao et al., 2008; Gao et al., 2008), with versatile binding and coordination modes. 1,10-Phenanthroline is also a good example for a bridging ligand that can link metal centres into extended networks, and a number of one-, two- and three- dimensional metal-1,10-phenanthroline frameworks have been generated (Chesnut et al., 1999). The reaction of 1H-benzimidazole-5,6-dicarboxylic acid with nickel chloride in an alkaline aqueous solution yielded a new Ni^II coordination polymer, whose crystal structure is reported here.

As illustrated in Figure 1, the Ni^II atom exhibits a slightly distorted octahedral coordination sphere, defined by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxylate ligands, two N atoms from one 1,10-phenanthroline ligand and two water molecules. The metal atoms are linked by bidentate 1H-benzimidazole-5,6-dicarboxylate groups into a linear chain (Fig. 2). Inter/intramolecular O—H···O and C—H···O hydrogen bonds between the carboxylate O atoms of 1H-benzimidazole-5,6-dicarboxylate and the coordinated water molecule lead to a two-dimensional layer (Fig. 3). The layers are further self-assembled into a three-dimensional supramolecular network by intermolecular N—H···O hydrogen bonds between the imidazole units and carboxylate groups (Table 1).

Related literature top

For background to 1H-benzimidazole-5,6-dicarboxylate complexes, see: Lo et al. (2007); Yao et al. (2008); Gao et al. (2008). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999).

Experimental top

A mixture of nickel chloride (1 mmol), 1H-benzimidazole-5,6-dicarboxylic acid (1 mmol), 1,10-phenanthroline (1 mmol), NaOH (1.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. [Symmetry codes: (i) x, 1/2 - y, 1/2 + z.
	Fig. 2. A view of the infinite chain of title compound.
	Fig. 3. A view of the two-dimensional layer constructed by O—H···O and C—H···O hydrogen bonding interactions.

catena-Poly[[diaqua(1,10-phenanthroline- κ²N,N')nickel(II)]-µ-1H-benzimidazole-5,6- dicarboxylato-κ²N³:O⁶] top

Crystal data top

[Ni(C₉H₄N₂O₄)(C₁₂H₈N₂)(H₂O)₂]	F(000) = 984
M_r = 479.09	D_x = 1.572 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3600 reflections
a = 10.021 (2) Å	θ = 1.4–28°
b = 16.980 (3) Å	µ = 1.01 mm⁻¹
c = 15.327 (5) Å	T = 293 K
β = 129.09 (2)°	Block, blue
V = 2024.3 (9) Å³	0.31 × 0.26 × 0.22 mm
Z = 4

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3639 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 25.2°, θ_min = 3.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −11→12
T_min = 0.746, T_max = 0.809	k = −20→20
15765 measured reflections	l = −18→18

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) = 0.091	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0565P)² + 0.2141P] where P = (F_o² + 2F_c²)/3
3639 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ni(C₉H₄N₂O₄)(C₁₂H₈N₂)(H₂O)₂]	V = 2024.3 (9) Å³
M_r = 479.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.021 (2) Å	µ = 1.01 mm⁻¹
b = 16.980 (3) Å	T = 293 K
c = 15.327 (5) Å	0.31 × 0.26 × 0.22 mm
β = 129.09 (2)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3639 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	3195 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.809	R_int = 0.039
15765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.09	Δρ_max = 0.37 e Å⁻³
3639 reflections	Δρ_min = −0.25 e Å⁻³
289 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	0.55530 (3)	0.434786 (13)	0.82246 (2)	0.02591 (11)
O1	0.38387 (19)	0.10540 (8)	0.49825 (13)	0.0398 (4)
O1W	0.76448 (17)	0.50597 (8)	0.94690 (12)	0.0318 (3)
H1W	0.7283	0.5441	0.9617	0.048*
H2W	0.8137	0.4736	1.0003	0.048*
O2	0.27333 (18)	0.22040 (9)	0.41361 (14)	0.0456 (4)
O2W	0.39504 (19)	0.49621 (9)	0.84828 (13)	0.0395 (4)
H3W	0.4521	0.5341	0.8920	0.059*
H4W	0.3796	0.4618	0.8805	0.059*
O3	0.59904 (17)	0.14247 (8)	0.43858 (11)	0.0314 (3)
O4	0.86749 (19)	0.10944 (10)	0.58603 (13)	0.0479 (4)
N1	0.7201 (2)	0.37301 (10)	0.80627 (14)	0.0296 (4)
N2	0.9708 (2)	0.34131 (11)	0.84962 (15)	0.0357 (4)
H2	1.0793	0.3421	0.8837	0.043*
N3	0.3234 (2)	0.38391 (10)	0.68890 (14)	0.0334 (4)
N5	0.4878 (3)	0.51071 (11)	0.69453 (16)	0.0407 (4)
C1	0.5577 (2)	0.22029 (11)	0.58394 (16)	0.0259 (4)
C2	0.7187 (2)	0.20098 (11)	0.61273 (16)	0.0277 (4)
C3	0.8679 (2)	0.23640 (12)	0.70388 (17)	0.0300 (4)
H3	0.9750	0.2227	0.7257	0.036*
C4	0.8508 (2)	0.29313 (12)	0.76130 (16)	0.0288 (4)
C5	0.6930 (2)	0.31336 (11)	0.73392 (16)	0.0261 (4)
C6	0.5439 (2)	0.27566 (11)	0.64394 (17)	0.0273 (4)
H6	0.4378	0.2875	0.6248	0.033*
C7	0.8876 (3)	0.38666 (13)	0.87258 (18)	0.0355 (5)
H7	0.9419	0.4241	0.9296	0.043*
C8	0.3932 (2)	0.17945 (12)	0.48969 (17)	0.0296 (4)
C9	0.7307 (2)	0.14601 (11)	0.54114 (17)	0.0297 (4)
C10	0.2431 (3)	0.32210 (15)	0.6884 (2)	0.0456 (6)
H10	0.2925	0.2953	0.7554	0.055*
C11	0.0856 (3)	0.29550 (19)	0.5899 (3)	0.0632 (8)
H11	0.0322	0.2514	0.5915	0.076*
C12	0.0117 (3)	0.33512 (19)	0.4919 (2)	0.0622 (8)
H12	−0.0927	0.3178	0.4263	0.075*
C13	0.0909 (3)	0.40118 (17)	0.4888 (2)	0.0523 (7)
C14	0.0237 (4)	0.4466 (2)	0.3894 (2)	0.0712 (9)
H14	−0.0821	0.4332	0.3217	0.085*
C15	0.1116 (5)	0.5081 (2)	0.3928 (2)	0.0775 (10)
H15	0.0667	0.5352	0.3268	0.093*
C16	0.2709 (4)	0.53257 (17)	0.4943 (2)	0.0600 (7)
C17	0.3695 (5)	0.59590 (19)	0.5046 (3)	0.0785 (10)
H17	0.3296	0.6257	0.4415	0.094*
C18	0.5209 (5)	0.61432 (19)	0.6043 (3)	0.0812 (10)
H18	0.5865	0.6558	0.6099	0.097*
C19	0.5781 (4)	0.57061 (14)	0.6991 (3)	0.0577 (7)
H19	0.6827	0.5836	0.7678	0.069*
C20	0.3383 (3)	0.49073 (13)	0.59409 (19)	0.0406 (5)
C21	0.2485 (3)	0.42380 (14)	0.59078 (19)	0.0391 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02516 (17)	0.02713 (17)	0.02261 (17)	0.00032 (8)	0.01370 (14)	0.00058 (9)
O1	0.0485 (9)	0.0309 (8)	0.0463 (9)	−0.0124 (6)	0.0330 (8)	−0.0050 (6)
O1W	0.0337 (8)	0.0273 (7)	0.0319 (8)	−0.0008 (5)	0.0196 (7)	−0.0031 (6)
O2	0.0250 (8)	0.0409 (9)	0.0475 (10)	0.0004 (6)	0.0117 (8)	−0.0029 (7)
O2W	0.0397 (8)	0.0405 (8)	0.0361 (9)	0.0052 (6)	0.0228 (8)	−0.0012 (6)
O3	0.0311 (7)	0.0347 (7)	0.0257 (7)	0.0014 (5)	0.0165 (7)	−0.0032 (6)
O4	0.0298 (8)	0.0577 (10)	0.0384 (9)	0.0097 (7)	0.0130 (7)	−0.0155 (8)
N1	0.0280 (9)	0.0324 (9)	0.0272 (9)	−0.0026 (6)	0.0168 (8)	−0.0065 (7)
N2	0.0222 (8)	0.0463 (10)	0.0297 (9)	−0.0029 (7)	0.0121 (8)	−0.0118 (8)
N3	0.0301 (9)	0.0417 (10)	0.0281 (9)	0.0000 (7)	0.0181 (8)	−0.0045 (7)
N5	0.0483 (11)	0.0373 (10)	0.0342 (10)	0.0045 (8)	0.0250 (10)	0.0062 (8)
C1	0.0247 (10)	0.0249 (9)	0.0250 (10)	−0.0008 (7)	0.0141 (9)	0.0011 (7)
C2	0.0266 (10)	0.0275 (10)	0.0249 (10)	0.0023 (7)	0.0142 (9)	0.0004 (8)
C3	0.0238 (9)	0.0356 (11)	0.0280 (10)	0.0020 (8)	0.0150 (9)	−0.0013 (8)
C4	0.0247 (9)	0.0324 (10)	0.0234 (10)	−0.0004 (7)	0.0123 (9)	−0.0004 (8)
C5	0.0273 (9)	0.0259 (9)	0.0253 (10)	0.0003 (7)	0.0167 (9)	0.0006 (8)
C6	0.0227 (9)	0.0301 (10)	0.0306 (11)	−0.0013 (7)	0.0175 (9)	−0.0022 (8)
C7	0.0290 (11)	0.0405 (12)	0.0309 (11)	−0.0045 (8)	0.0159 (10)	−0.0123 (9)
C8	0.0283 (10)	0.0314 (11)	0.0331 (11)	−0.0057 (8)	0.0212 (9)	−0.0058 (8)
C9	0.0251 (10)	0.0316 (10)	0.0296 (11)	−0.0026 (8)	0.0160 (9)	−0.0027 (8)
C10	0.0447 (13)	0.0568 (15)	0.0428 (13)	−0.0148 (11)	0.0311 (12)	−0.0131 (11)
C11	0.0558 (16)	0.084 (2)	0.0632 (19)	−0.0333 (15)	0.0437 (16)	−0.0301 (16)
C12	0.0387 (14)	0.091 (2)	0.0433 (16)	−0.0135 (13)	0.0195 (13)	−0.0268 (15)
C13	0.0389 (13)	0.0677 (17)	0.0340 (13)	0.0058 (12)	0.0152 (12)	−0.0118 (12)
C14	0.0542 (18)	0.091 (2)	0.0265 (14)	0.0131 (15)	0.0055 (14)	−0.0051 (13)
C15	0.085 (2)	0.079 (2)	0.0324 (15)	0.0178 (18)	0.0202 (16)	0.0141 (14)
C16	0.0776 (19)	0.0562 (16)	0.0387 (14)	0.0174 (14)	0.0330 (15)	0.0119 (12)
C17	0.110 (3)	0.0605 (19)	0.056 (2)	0.0062 (18)	0.048 (2)	0.0265 (15)
C18	0.112 (3)	0.0601 (19)	0.069 (2)	−0.0128 (18)	0.056 (2)	0.0185 (16)
C19	0.0712 (19)	0.0452 (15)	0.0536 (17)	−0.0087 (12)	0.0378 (16)	0.0068 (11)
C20	0.0473 (13)	0.0392 (12)	0.0311 (12)	0.0119 (9)	0.0227 (11)	0.0060 (9)
C21	0.0332 (12)	0.0501 (13)	0.0249 (11)	0.0109 (9)	0.0140 (10)	−0.0035 (9)

Geometric parameters (Å, º) top

Ni1—O3ⁱ	2.0241 (14)	C2—C9	1.502 (3)
Ni1—N5	2.0715 (19)	C3—C4	1.386 (3)
Ni1—N3	2.0828 (18)	C3—H3	0.9300
Ni1—N1	2.0994 (16)	C4—C5	1.399 (3)
Ni1—O1W	2.1098 (15)	C5—C6	1.395 (3)
Ni1—O2W	2.1507 (15)	C6—H6	0.9300
O1—C8	1.274 (2)	C7—H7	0.9300
O1W—H1W	0.8402	C10—C11	1.404 (3)
O1W—H2W	0.8401	C10—H10	0.9300
O2—C8	1.233 (2)	C11—C12	1.362 (4)
O2W—H3W	0.8400	C11—H11	0.9300
O2W—H4W	0.8400	C12—C13	1.392 (4)
O3—C9	1.265 (2)	C12—H12	0.9300
O3—Ni1ⁱⁱ	2.0241 (14)	C13—C21	1.404 (3)
O4—C9	1.244 (2)	C13—C14	1.441 (4)
N1—C7	1.323 (3)	C14—C15	1.345 (5)
N1—C5	1.396 (3)	C14—H14	0.9300
N2—C7	1.335 (3)	C15—C16	1.418 (4)
N2—C4	1.376 (3)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.400 (5)
N3—C10	1.319 (3)	C16—C20	1.413 (3)
N3—C21	1.364 (3)	C17—C18	1.346 (5)
N5—C19	1.334 (3)	C17—H17	0.9300
N5—C20	1.350 (3)	C18—C19	1.393 (4)
C1—C6	1.381 (3)	C18—H18	0.9300
C1—C2	1.417 (3)	C19—H19	0.9300
C1—C8	1.510 (3)	C20—C21	1.431 (3)
C2—C3	1.384 (3)

O3ⁱ—Ni1—N5	174.88 (7)	C1—C6—C5	118.45 (17)
O3ⁱ—Ni1—N3	94.83 (7)	C1—C6—H6	120.8
N5—Ni1—N3	80.31 (8)	C5—C6—H6	120.8
O3ⁱ—Ni1—N1	91.71 (6)	N1—C7—N2	113.37 (18)
N5—Ni1—N1	90.62 (8)	N1—C7—H7	123.3
N3—Ni1—N1	98.62 (7)	N2—C7—H7	123.3
O3ⁱ—Ni1—O1W	92.03 (6)	O2—C8—O1	124.26 (18)
N5—Ni1—O1W	92.56 (7)	O2—C8—C1	118.08 (18)
N3—Ni1—O1W	169.42 (6)	O1—C8—C1	117.48 (17)
N1—Ni1—O1W	89.19 (6)	O4—C9—O3	125.86 (19)
O3ⁱ—Ni1—O2W	85.71 (6)	O4—C9—C2	118.28 (17)
N5—Ni1—O2W	92.07 (7)	O3—C9—C2	115.85 (16)
N3—Ni1—O2W	83.24 (7)	N3—C10—C11	122.1 (2)
N1—Ni1—O2W	176.95 (6)	N3—C10—H10	119.0
O1W—Ni1—O2W	89.27 (6)	C11—C10—H10	119.0
Ni1—O1W—H1W	109.5	C12—C11—C10	119.2 (3)
Ni1—O1W—H2W	98.3	C12—C11—H11	120.4
H1W—O1W—H2W	109.2	C10—C11—H11	120.4
Ni1—O2W—H3W	107.8	C11—C12—C13	120.7 (2)
Ni1—O2W—H4W	102.0	C11—C12—H12	119.6
H3W—O2W—H4W	110.4	C13—C12—H12	119.6
C9—O3—Ni1ⁱⁱ	126.97 (12)	C12—C13—C21	116.6 (2)
C7—N1—C5	104.75 (16)	C12—C13—C14	124.8 (3)
C7—N1—Ni1	122.19 (14)	C21—C13—C14	118.6 (3)
C5—N1—Ni1	133.06 (13)	C15—C14—C13	121.1 (3)
C7—N2—C4	107.40 (17)	C15—C14—H14	119.5
C7—N2—H2	126.3	C13—C14—H14	119.5
C4—N2—H2	126.3	C14—C15—C16	121.8 (3)
C10—N3—C21	118.60 (19)	C14—C15—H15	119.1
C10—N3—Ni1	129.35 (15)	C16—C15—H15	119.1
C21—N3—Ni1	112.04 (15)	C17—C16—C15	125.1 (3)
C19—N5—C20	118.7 (2)	C17—C16—C20	116.3 (3)
C19—N5—Ni1	128.25 (18)	C15—C16—C20	118.6 (3)
C20—N5—Ni1	112.85 (15)	C18—C17—C16	121.1 (3)
C6—C1—C2	121.47 (17)	C18—C17—H17	119.5
C6—C1—C8	116.26 (16)	C16—C17—H17	119.5
C2—C1—C8	122.22 (17)	C17—C18—C19	119.2 (3)
C3—C2—C1	120.47 (18)	C17—C18—H18	120.4
C3—C2—C9	118.32 (17)	C19—C18—H18	120.4
C1—C2—C9	121.09 (16)	N5—C19—C18	122.2 (3)
C4—C3—C2	117.13 (18)	N5—C19—H19	118.9
C4—C3—H3	121.4	C18—C19—H19	118.9
C2—C3—H3	121.4	N5—C20—C16	122.5 (2)
N2—C4—C3	131.06 (18)	N5—C20—C21	117.47 (19)
N2—C4—C5	105.66 (17)	C16—C20—C21	120.0 (2)
C3—C4—C5	123.27 (18)	N3—C21—C13	122.9 (2)
N1—C5—C6	131.99 (17)	N3—C21—C20	117.3 (2)
N1—C5—C4	108.82 (16)	C13—C21—C20	119.8 (2)
C6—C5—C4	119.16 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱⁱⁱ	0.84	1.90	2.710 (2)	163
O1W—H2W···O4ⁱ	0.84	1.76	2.584 (2)	165
O2W—H3W···O1ⁱⁱⁱ	0.84	1.87	2.703 (2)	169
O2W—H4W···O1ⁱ	0.84	2.11	2.932 (2)	165
N2—H2···O2^iv	0.86	2.00	2.739 (2)	144
N2—H2···O1^iv	0.86	2.54	3.355 (2)	159
C10—H10···O2ⁱ	0.93	2.56	3.346 (8)	143

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₄N₂O₄)(C₁₂H₈N₂)(H₂O)₂]
M_r	479.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.021 (2), 16.980 (3), 15.327 (5)
β (°)	129.09 (2)
V (Å³)	2024.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.31 × 0.26 × 0.22

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.746, 0.809
No. of measured, independent and observed [I > 2σ(I)] reflections	15765, 3639, 3195
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.09
No. of reflections	3639
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.25

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱ	0.84	1.90	2.710 (2)	162.8
O1W—H2W···O4ⁱⁱ	0.84	1.76	2.584 (2)	164.6
O2W—H3W···O1ⁱ	0.84	1.87	2.703 (2)	168.9
O2W—H4W···O1ⁱⁱ	0.84	2.11	2.932 (2)	165.0
N2—H2···O2ⁱⁱⁱ	0.86	2.00	2.739 (2)	143.8
N2—H2···O1ⁱⁱⁱ	0.86	2.54	3.355 (2)	159.2
C10—H10···O2ⁱⁱ	0.93	2.56	3.346 (8)	143

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for support of this work.

References

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