Tetra­kis(1H-imidazole-κN3)(2-phenyl­propanedioato-κ2O1,O3)nickel(II)

Zhang, K.-L.; Diao, G.-W.; Ng, S.W.

doi:10.1107/S1600536810041577

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1430

https://doi.org/10.1107/S1600536810041577

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Tetrakis(1H-imidazole-κN³)(2-phenylpropanedioato-κ²O¹,O³)nickel(II)

Kou-Lin Zhang,^a Guo-Wang Diao ^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 12 October 2010; accepted 14 October 2010; online 23 October 2010)

In the title complex, [Ni(C₉H₆O₄)(C₃H₄N₂)₄], the Ni^II ion is O,O′-chelated by the phenylmalonato ligand and coordinated by four imidazole ligands in a slightly distorted octahedral geometry. In the crystal structure, symmetry-related molecules are linked by N—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For the cobalt(II) analog, see: Zhang et al. (2007 ).

Experimental

Crystal data

[Ni(C₉H₆O₄)(C₃H₄N₂)₄]
M_r = 509.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.5358 (8) Å
b = 13.3148 (12) Å
c = 20.6996 (19) Å
V = 2352.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.812, T_max = 0.881
15962 measured reflections
5516 independent reflections
4013 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.086
S = 0.98
5516 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 2344 Friedel pairs
Flack parameter: 0.082 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.88	2.06	2.943 (3)	176
N4—H4⋯O1ⁱⁱ	0.88	1.97	2.839 (3)	168
N6—H6⋯O2ⁱⁱⁱ	0.88	1.90	2.774 (3)	172
N8—H8⋯O4^iv	0.88	1.85	2.718 (3)	169
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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: https://doi.org/10.1107/S1600536810041577/lh5153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041577/lh5153Isup2.hkl

checkCIF report

Comment top

We have previously reported the crystal structure of the tetrakis(imidazole) adduct of cobalt(II) phenylmalonate. The structure features the carboxylate-chelated cobalt(II) atom bonded to four N-heterocycles; each of these has a nitrogen-donor site that enables the octahedrally coordinated mononuclear molecule to connect with each other to form a three-dimensional network (Zhang et al., 2007). The nickel analog (Fig. 1) is isostructural, the two compounds crystallizing with similar unit cell dimensions.

Related literature top

For the cobalt(II) analog, see: Zhang et al. (2007).

Experimental top

Imidazole (0.339 g. 0.56 mmol) was dissolved in methanol (10 ml) and to the solution was added nickel nitrate hexahydrate (0.480 g, 1.65 mmol) dissolved in water (6 ml). To the clear soluiton was added phenylmalonic acid (0.300 g, 1.65 mmol) and sodium hydroxide (0.120 g, 3.30 mmol) dissolved in water (10 ml). The filtered solution was set aside for the growth of green crystals over several days; yield 50%. CH&N elemental analysis. Calc. for C₂₁H₂₂N₈NiO₄: C 49.53, H 4.36, N 22.00%. Found: C 49.61, H 4.49, N 21.91%.

Structure description top

For the cobalt(II) analog, see: Zhang et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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. Thermal ellipsoid plot (Barbour, 2001) of Ni(C₃H₄N₂)₄(C₉H₆O₄) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Tetrakis(1H-imidazole-κN³)(2-phenylpropanedioato- κ²O¹,O³)nickel(II) top

Crystal data top

[Ni(C₉H₆O₄)(C₃H₄N₂)₄]	F(000) = 1056
M_r = 509.18	D_x = 1.438 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2481 reflections
a = 8.5358 (8) Å	θ = 2.6–21.7°
b = 13.3148 (12) Å	µ = 0.87 mm⁻¹
c = 20.6996 (19) Å	T = 293 K
V = 2352.6 (4) Å³	Prism, green
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	5516 independent reflections
Radiation source: fine-focus sealed tube	4013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.812, T_max = 0.881	k = −17→17
15962 measured reflections	l = −19→27

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0326P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
5516 reflections	Δρ_max = 0.41 e Å⁻³
307 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2344 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.082 (13)

Crystal data top

[Ni(C₉H₆O₄)(C₃H₄N₂)₄]	V = 2352.6 (4) Å³
M_r = 509.18	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5358 (8) Å	µ = 0.87 mm⁻¹
b = 13.3148 (12) Å	T = 293 K
c = 20.6996 (19) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	5516 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4013 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.881	R_int = 0.051
15962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.41 e Å⁻³
S = 0.98	Δρ_min = −0.31 e Å⁻³
5516 reflections	Absolute structure: Flack (1983), 2344 Friedel pairs
307 parameters	Absolute structure parameter: 0.082 (13)
0 restraints

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

	x	y	z	U_iso*/U_eq
Ni1	0.66167 (4)	0.40568 (3)	0.336577 (18)	0.02636 (10)
O1	0.8851 (2)	0.40575 (17)	0.29819 (9)	0.0324 (4)
O2	1.0679 (2)	0.37546 (16)	0.22649 (12)	0.0433 (6)
O3	0.5823 (2)	0.41866 (15)	0.24132 (9)	0.0323 (5)
O4	0.6203 (3)	0.43579 (17)	0.13674 (11)	0.0515 (7)
N1	0.6652 (3)	0.24683 (16)	0.33088 (13)	0.0338 (6)
N2	0.5969 (3)	0.0939 (2)	0.30389 (16)	0.0597 (9)
H2	0.5388	0.0432	0.2908	0.072*
N3	0.4310 (2)	0.4058 (2)	0.37002 (11)	0.0301 (5)
N4	0.1739 (3)	0.4091 (2)	0.36620 (12)	0.0388 (6)
H4	0.0782	0.4110	0.3504	0.047*
N5	0.6703 (3)	0.56328 (16)	0.33579 (12)	0.0312 (5)
N6	0.7570 (3)	0.7169 (2)	0.32201 (14)	0.0424 (8)
H6	0.8180	0.7667	0.3098	0.051*
N7	0.7489 (3)	0.4034 (2)	0.43160 (11)	0.0324 (6)
N8	0.8143 (4)	0.4576 (2)	0.52810 (14)	0.0500 (8)
H8	0.8359	0.4991	0.5599	0.060*
C1	0.9291 (3)	0.3761 (2)	0.24304 (17)	0.0300 (7)
C2	0.8045 (3)	0.3333 (2)	0.19607 (15)	0.0343 (8)
H2A	0.7662	0.2713	0.2161	0.041*
C3	0.6602 (3)	0.4033 (2)	0.19068 (14)	0.0315 (6)
C4	0.8732 (3)	0.3022 (2)	0.13164 (16)	0.0361 (8)
C5	0.8607 (4)	0.2032 (3)	0.11128 (17)	0.0468 (9)
H5	0.8055	0.1569	0.1360	0.056*
C6	0.9301 (5)	0.1738 (3)	0.0545 (2)	0.0635 (12)
H6A	0.9202	0.1075	0.0410	0.076*
C7	1.0126 (5)	0.2392 (4)	0.0179 (2)	0.0683 (13)
H7	1.0602	0.2173	−0.0199	0.082*
C8	1.0264 (5)	0.3368 (3)	0.0363 (2)	0.0643 (12)
H8A	1.0831	0.3817	0.0110	0.077*
C9	0.9556 (4)	0.3689 (3)	0.09264 (17)	0.0471 (9)
H9	0.9632	0.4360	0.1047	0.057*
C10	0.5503 (4)	0.1886 (2)	0.31110 (17)	0.0450 (9)
H10	0.4488	0.2108	0.3031	0.054*
C11	0.7919 (4)	0.1839 (2)	0.3360 (2)	0.0493 (9)
H11	0.8920	0.2036	0.3484	0.059*
C12	0.7502 (4)	0.0899 (3)	0.3204 (2)	0.0626 (12)
H12	0.8139	0.0333	0.3208	0.075*
C13	0.3064 (3)	0.4087 (2)	0.33245 (16)	0.0361 (7)
H13	0.3106	0.4102	0.2876	0.043*
C14	0.3722 (3)	0.4050 (3)	0.43166 (15)	0.0391 (7)
H14	0.4318	0.4040	0.4693	0.047*
C15	0.2137 (4)	0.4060 (3)	0.42918 (17)	0.0446 (8)
H15	0.1454	0.4048	0.4642	0.054*
C16	0.7835 (4)	0.6195 (2)	0.31334 (16)	0.0383 (8)
H16	0.8728	0.5941	0.2935	0.046*
C17	0.5650 (4)	0.6304 (2)	0.36077 (17)	0.0427 (9)
H17	0.4705	0.6132	0.3802	0.051*
C18	0.6178 (4)	0.7249 (2)	0.35329 (17)	0.0426 (9)
H18	0.5690	0.7837	0.3668	0.051*
C19	0.7768 (4)	0.4830 (3)	0.46802 (16)	0.0392 (8)
H19	0.7709	0.5489	0.4533	0.047*
C20	0.7710 (5)	0.3241 (3)	0.47194 (18)	0.0585 (12)
H20	0.7590	0.2571	0.4604	0.070*
C21	0.8133 (6)	0.3571 (3)	0.53140 (18)	0.0682 (13)
H21	0.8368	0.3179	0.5673	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02413 (16)	0.02630 (16)	0.02864 (19)	−0.00065 (17)	−0.00168 (18)	−0.00153 (19)
O1	0.0262 (10)	0.0397 (11)	0.0312 (11)	−0.0002 (10)	0.0005 (9)	−0.0080 (11)
O2	0.0255 (11)	0.0565 (15)	0.0479 (15)	0.0019 (10)	0.0034 (11)	−0.0166 (12)
O3	0.0296 (10)	0.0422 (13)	0.0252 (11)	0.0041 (10)	0.0009 (9)	−0.0002 (10)
O4	0.0486 (14)	0.0700 (17)	0.0359 (14)	0.0183 (12)	0.0071 (12)	0.0217 (12)
N1	0.0380 (13)	0.0312 (13)	0.0322 (15)	−0.0052 (12)	−0.0028 (18)	0.0004 (11)
N2	0.0581 (18)	0.0281 (14)	0.093 (3)	−0.0143 (16)	−0.0013 (17)	−0.0146 (18)
N3	0.0258 (11)	0.0332 (12)	0.0313 (14)	−0.0023 (13)	−0.0017 (11)	−0.0005 (14)
N4	0.0232 (11)	0.0497 (15)	0.0436 (15)	0.0030 (15)	−0.0003 (13)	0.0011 (15)
N5	0.0278 (12)	0.0303 (12)	0.0356 (14)	−0.0031 (10)	0.0006 (17)	−0.0003 (11)
N6	0.0387 (15)	0.0343 (15)	0.054 (2)	−0.0088 (13)	−0.0008 (14)	0.0059 (15)
N7	0.0331 (12)	0.0349 (13)	0.0291 (14)	0.0015 (13)	−0.0029 (11)	−0.0033 (15)
N8	0.064 (2)	0.053 (2)	0.0330 (18)	0.0026 (18)	−0.0074 (17)	−0.0125 (15)
C1	0.0243 (15)	0.0255 (16)	0.040 (2)	0.0061 (12)	−0.0016 (14)	−0.0010 (13)
C2	0.0326 (18)	0.0358 (17)	0.0346 (18)	−0.0004 (14)	0.0001 (15)	0.0012 (15)
C3	0.0283 (13)	0.0343 (14)	0.0319 (15)	−0.0006 (18)	0.0009 (14)	−0.0023 (15)
C4	0.0273 (16)	0.049 (2)	0.0322 (17)	0.0077 (15)	−0.0009 (14)	−0.0051 (16)
C5	0.0362 (18)	0.051 (2)	0.053 (2)	0.0041 (18)	−0.0058 (18)	−0.0053 (18)
C6	0.064 (3)	0.069 (3)	0.057 (3)	0.018 (2)	−0.007 (2)	−0.031 (2)
C7	0.075 (3)	0.088 (3)	0.042 (3)	0.032 (3)	−0.001 (2)	−0.013 (2)
C8	0.060 (3)	0.088 (3)	0.045 (3)	0.018 (2)	0.015 (2)	0.015 (2)
C9	0.052 (2)	0.048 (2)	0.042 (2)	0.0090 (17)	0.0023 (19)	0.0043 (17)
C10	0.0379 (18)	0.0350 (18)	0.062 (3)	−0.0055 (15)	0.0071 (17)	−0.0004 (17)
C11	0.0431 (19)	0.0379 (18)	0.067 (3)	0.0085 (14)	−0.018 (2)	−0.004 (2)
C12	0.056 (2)	0.0342 (19)	0.098 (4)	0.006 (2)	−0.009 (2)	−0.003 (3)
C13	0.0293 (14)	0.0416 (16)	0.0374 (17)	−0.0031 (14)	−0.0022 (14)	−0.0015 (19)
C14	0.0350 (16)	0.0509 (18)	0.0313 (17)	0.0019 (18)	−0.0008 (14)	0.0026 (18)
C15	0.0366 (16)	0.056 (2)	0.041 (2)	0.0009 (19)	0.0089 (15)	0.006 (2)
C16	0.0365 (17)	0.0314 (19)	0.047 (2)	0.0011 (13)	0.0027 (15)	−0.0013 (15)
C17	0.0347 (17)	0.0400 (18)	0.053 (2)	0.0016 (14)	0.0081 (17)	0.0003 (16)
C18	0.0430 (19)	0.0261 (16)	0.059 (3)	0.0068 (14)	0.0016 (17)	0.0031 (15)
C19	0.0401 (19)	0.044 (2)	0.034 (2)	−0.0004 (16)	−0.0038 (16)	−0.0028 (17)
C20	0.102 (3)	0.038 (2)	0.036 (2)	0.003 (2)	−0.020 (2)	0.0050 (17)
C21	0.112 (4)	0.057 (3)	0.036 (2)	0.006 (3)	−0.025 (3)	0.0050 (19)

Geometric parameters (Å, º) top

Ni1—O1	2.0662 (18)	C2—C4	1.515 (4)
Ni1—N3	2.087 (2)	C2—C3	1.549 (4)
Ni1—O3	2.092 (2)	C2—H2A	0.9800
Ni1—N5	2.100 (2)	C4—C5	1.388 (5)
Ni1—N7	2.103 (2)	C4—C9	1.391 (4)
Ni1—N1	2.118 (2)	C5—C6	1.372 (5)
O1—C1	1.265 (4)	C5—H5	0.9300
O2—C1	1.234 (3)	C6—C7	1.352 (6)
O3—C3	1.258 (3)	C6—H6A	0.9300
O4—C3	1.245 (3)	C7—C8	1.359 (5)
N1—C10	1.316 (4)	C7—H7	0.9300
N1—C11	1.373 (4)	C8—C9	1.382 (5)
N2—C10	1.330 (4)	C8—H8A	0.9300
N2—C12	1.353 (4)	C9—H9	0.9300
N2—H2	0.8800	C10—H10	0.9300
N3—C13	1.318 (3)	C11—C12	1.340 (5)
N3—C14	1.371 (4)	C11—H11	0.9300
N4—C13	1.329 (3)	C12—H12	0.9300
N4—C15	1.348 (4)	C13—H13	0.9300
N4—H4	0.8800	C14—C15	1.355 (4)
N5—C16	1.308 (4)	C14—H14	0.9300
N5—C17	1.369 (4)	C15—H15	0.9300
N6—C16	1.329 (4)	C16—H16	0.9300
N6—C18	1.357 (4)	C17—C18	1.345 (4)
N6—H6	0.8800	C17—H17	0.9300
N7—C19	1.323 (4)	C18—H18	0.9300
N7—C20	1.359 (4)	C19—H19	0.9300
N8—C19	1.328 (4)	C20—C21	1.356 (5)
N8—C21	1.339 (4)	C20—H20	0.9300
N8—H8	0.8800	C21—H21	0.9300
C1—C2	1.550 (4)

O1—Ni1—N3	176.75 (9)	C5—C4—C2	119.8 (3)
O1—Ni1—O3	86.37 (7)	C9—C4—C2	122.2 (3)
N3—Ni1—O3	90.39 (8)	C6—C5—C4	119.9 (4)
O1—Ni1—N5	87.95 (9)	C6—C5—H5	120.1
N3—Ni1—N5	91.98 (10)	C4—C5—H5	120.1
O3—Ni1—N5	85.50 (9)	C7—C6—C5	121.4 (4)
O1—Ni1—N7	91.88 (8)	C7—C6—H6A	119.3
N3—Ni1—N7	91.36 (9)	C5—C6—H6A	119.3
O3—Ni1—N7	175.72 (9)	C6—C7—C8	120.3 (4)
N5—Ni1—N7	90.54 (10)	C6—C7—H7	119.9
O1—Ni1—N1	88.05 (10)	C8—C7—H7	119.9
N3—Ni1—N1	91.88 (10)	C7—C8—C9	119.6 (4)
O3—Ni1—N1	91.98 (9)	C7—C8—H8A	120.2
N5—Ni1—N1	175.40 (10)	C9—C8—H8A	120.2
N7—Ni1—N1	91.87 (10)	C8—C9—C4	120.9 (4)
C1—O1—Ni1	128.36 (18)	C8—C9—H9	119.5
C3—O3—Ni1	126.92 (18)	C4—C9—H9	119.5
C10—N1—C11	104.6 (2)	N1—C10—N2	111.8 (3)
C10—N1—Ni1	126.6 (2)	N1—C10—H10	124.1
C11—N1—Ni1	128.0 (2)	N2—C10—H10	124.1
C10—N2—C12	107.3 (3)	C12—C11—N1	110.0 (3)
C10—N2—H2	126.3	C12—C11—H11	125.0
C12—N2—H2	126.3	N1—C11—H11	125.0
C13—N3—C14	104.7 (2)	C11—C12—N2	106.3 (4)
C13—N3—Ni1	124.44 (19)	C11—C12—H12	126.8
C14—N3—Ni1	130.84 (18)	N2—C12—H12	126.8
C13—N4—C15	107.1 (2)	N3—C13—N4	112.1 (3)
C13—N4—H4	126.5	N3—C13—H13	123.9
C15—N4—H4	126.5	N4—C13—H13	123.9
C16—N5—C17	104.2 (3)	C15—C14—N3	109.3 (3)
C16—N5—Ni1	126.9 (2)	C15—C14—H14	125.4
C17—N5—Ni1	128.8 (2)	N3—C14—H14	125.4
C16—N6—C18	106.8 (3)	N4—C15—C14	106.8 (3)
C16—N6—H6	126.6	N4—C15—H15	126.6
C18—N6—H6	126.6	C14—C15—H15	126.6
C19—N7—C20	104.3 (3)	N5—C16—N6	112.7 (3)
C19—N7—Ni1	125.8 (2)	N5—C16—H16	123.7
C20—N7—Ni1	129.4 (2)	N6—C16—H16	123.7
C19—N8—C21	107.5 (3)	C18—C17—N5	110.3 (3)
C19—N8—H8	126.2	C18—C17—H17	124.8
C21—N8—H8	126.2	N5—C17—H17	124.8
O2—C1—O1	122.5 (3)	C17—C18—N6	106.0 (3)
O2—C1—C2	118.9 (3)	C17—C18—H18	127.0
O1—C1—C2	118.5 (3)	N6—C18—H18	127.0
C4—C2—C3	114.1 (2)	N7—C19—N8	111.9 (3)
C4—C2—C1	112.8 (2)	N7—C19—H19	124.1
C3—C2—C1	111.7 (2)	N8—C19—H19	124.1
C4—C2—H2A	105.8	C21—C20—N7	110.1 (3)
C3—C2—H2A	105.8	C21—C20—H20	125.0
C1—C2—H2A	105.8	N7—C20—H20	125.0
O4—C3—O3	123.1 (3)	N8—C21—C20	106.2 (4)
O4—C3—C2	119.4 (3)	N8—C21—H21	126.9
O3—C3—C2	117.2 (3)	C20—C21—H21	126.9
C5—C4—C9	118.0 (3)

O3—Ni1—O1—C1	−28.3 (3)	Ni1—O3—C3—O4	−161.4 (2)
N5—Ni1—O1—C1	−113.9 (3)	Ni1—O3—C3—C2	23.8 (4)
N7—Ni1—O1—C1	155.7 (3)	C4—C2—C3—O4	−6.3 (4)
N1—Ni1—O1—C1	63.9 (3)	C1—C2—C3—O4	123.0 (3)
O1—Ni1—O3—C3	15.1 (2)	C4—C2—C3—O3	168.7 (3)
N3—Ni1—O3—C3	−164.7 (2)	C1—C2—C3—O3	−61.9 (4)
N5—Ni1—O3—C3	103.4 (2)	C3—C2—C4—C5	−111.2 (3)
N1—Ni1—O3—C3	−72.8 (2)	C1—C2—C4—C5	120.0 (3)
O1—Ni1—N1—C10	−137.2 (3)	C3—C2—C4—C9	71.8 (4)
N3—Ni1—N1—C10	39.6 (3)	C1—C2—C4—C9	−57.1 (4)
O3—Ni1—N1—C10	−50.9 (3)	C9—C4—C5—C6	0.6 (5)
N7—Ni1—N1—C10	131.0 (3)	C2—C4—C5—C6	−176.6 (3)
O1—Ni1—N1—C11	30.7 (3)	C4—C5—C6—C7	0.8 (6)
N3—Ni1—N1—C11	−152.6 (3)	C5—C6—C7—C8	−1.1 (7)
O3—Ni1—N1—C11	117.0 (3)	C6—C7—C8—C9	0.1 (7)
N7—Ni1—N1—C11	−61.1 (3)	C7—C8—C9—C4	1.4 (6)
O3—Ni1—N3—C13	2.8 (3)	C5—C4—C9—C8	−1.7 (5)
N5—Ni1—N3—C13	88.3 (3)	C2—C4—C9—C8	175.4 (3)
N7—Ni1—N3—C13	178.9 (3)	C11—N1—C10—N2	0.3 (4)
N1—Ni1—N3—C13	−89.2 (3)	Ni1—N1—C10—N2	170.4 (2)
O3—Ni1—N3—C14	−175.9 (3)	C12—N2—C10—N1	0.5 (4)
N5—Ni1—N3—C14	−90.4 (3)	C10—N1—C11—C12	−1.0 (4)
N7—Ni1—N3—C14	0.2 (3)	Ni1—N1—C11—C12	−171.0 (3)
N1—Ni1—N3—C14	92.1 (3)	N1—C11—C12—N2	1.3 (5)
O1—Ni1—N5—C16	3.4 (3)	C10—N2—C12—C11	−1.1 (5)
N3—Ni1—N5—C16	−173.4 (3)	C14—N3—C13—N4	−0.4 (4)
O3—Ni1—N5—C16	−83.1 (3)	Ni1—N3—C13—N4	−179.4 (2)
N7—Ni1—N5—C16	95.3 (3)	C15—N4—C13—N3	−0.2 (4)
O1—Ni1—N5—C17	−173.2 (3)	C13—N3—C14—C15	0.8 (4)
N3—Ni1—N5—C17	10.1 (3)	Ni1—N3—C14—C15	179.7 (2)
O3—Ni1—N5—C17	100.3 (3)	C13—N4—C15—C14	0.7 (4)
N7—Ni1—N5—C17	−81.3 (3)	N3—C14—C15—N4	−1.0 (4)
O1—Ni1—N7—C19	92.3 (2)	C17—N5—C16—N6	−0.3 (4)
N3—Ni1—N7—C19	−87.6 (3)	Ni1—N5—C16—N6	−177.6 (2)
N5—Ni1—N7—C19	4.4 (3)	C18—N6—C16—N5	1.1 (4)
N1—Ni1—N7—C19	−179.5 (3)	C16—N5—C17—C18	−0.5 (4)
O1—Ni1—N7—C20	−96.5 (3)	Ni1—N5—C17—C18	176.7 (2)
N3—Ni1—N7—C20	83.5 (3)	N5—C17—C18—N6	1.2 (4)
N5—Ni1—N7—C20	175.5 (3)	C16—N6—C18—C17	−1.3 (4)
N1—Ni1—N7—C20	−8.4 (3)	C20—N7—C19—N8	−0.1 (4)
Ni1—O1—C1—O2	−176.5 (2)	Ni1—N7—C19—N8	172.8 (2)
Ni1—O1—C1—C2	−0.1 (4)	C21—N8—C19—N7	0.9 (5)
O2—C1—C2—C4	−4.3 (4)	C19—N7—C20—C21	−0.6 (5)
O1—C1—C2—C4	179.1 (3)	Ni1—N7—C20—C21	−173.2 (3)
O2—C1—C2—C3	−134.4 (3)	C19—N8—C21—C20	−1.2 (6)
O1—C1—C2—C3	49.0 (4)	N7—C20—C21—N8	1.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.88	2.06	2.943 (3)	176
N4—H4···O1ⁱⁱ	0.88	1.97	2.839 (3)	168
N6—H6···O2ⁱⁱⁱ	0.88	1.90	2.774 (3)	172
N8—H8···O4^iv	0.88	1.85	2.718 (3)	169

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₆O₄)(C₃H₄N₂)₄]
M_r	509.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.5358 (8), 13.3148 (12), 20.6996 (19)
V (Å³)	2352.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.812, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	15962, 5516, 4013
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.086, 0.98
No. of reflections	5516
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.31
Absolute structure	Flack (1983), 2344 Friedel pairs
Absolute structure parameter	0.082 (13)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.88	2.06	2.943 (3)	176
N4—H4···O1ⁱⁱ	0.88	1.97	2.839 (3)	168
N6—H6···O2ⁱⁱⁱ	0.88	1.90	2.774 (3)	172
N8—H8···O4^iv	0.88	1.85	2.718 (3)	169

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

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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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
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