Crystal structure of poly[di­aqua­(μ2-benzene-1,4-di­carboxyl­ato-κ2O1:O4)(μ2-benzene-1,4-di­carboxyl­ato-κ4O1,O1′:O4,O4′)bis­(μ2-3,3′,5,5′-tetra­methyl-4,4′-bi­pyrazole-κ2N:N′)dinickel(II)]

Wu, C.; Cao, P.

doi:10.1107/S2056989015008415

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages m127-m128

doi:10.1107/S2056989015008415

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Crystal structure of poly[diaqua(μ₂-benzene-1,4-dicarboxylato-κ²O¹:O⁴)(μ₂-benzene-1,4-dicarboxylato-κ⁴O¹,O^1′:O⁴,O^4′)bis(μ₂-3,3′,5,5′-tetramethyl-4,4′-bipyrazole-κ²N:N′)dinickel(II)]

Chao Wu ^a and Peng Cao ^a ^*

^aSchool of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, Guangdong, People's Republic of China
^*Correspondence e-mail: g_jhe@126.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 22 April 2015; accepted 28 April 2015; online 7 May 2015)

The asymmetric unit of the polymeric title compound, [Ni(C₈H₄O₄)(C₁₀H₁₄N₄)(H₂O)]_n, contains one Ni²⁺ cation, one coordinating water molecule, one 3,3′,5,5′-tetramethyl-4,4′-bipyrazole ligand and half each of two benzene-1,4-dicarboxylate anions, the other halves being generated by inversion symmetry. The Ni²⁺ cation exhibits an octahedral N₂O₄ coordination sphere defined by the O atoms of the water molecule and two different anions and the N atoms of two symmetry-related N-heterocycles. The N-heterocycles and both anions bridge adjacent Ni²⁺ cations into a three-dimensional network structure, with one of the anions in a bis-bidentate and the other in a bis-monodentate bridging mode. N—H⋯O and O—H⋯O hydrogen bonds between the N-heterocycles and water molecules as donor groups and the carboxylate O atoms as acceptor groups consolidate the crystal packing.

Keywords: crystal structure; nickel; coordination polymer; hydrogen bonding.

CCDC reference: 1062289

1. Related literature

In the related water-free coordination polymer {[Zn(terephthalate)(H₂Bpz)]·0.5(H₂Bpz)}_n (H₂Bpz = 3,3′,5,5′-tetramethyl-4,4′-bipyrazole), the Zn²⁺ cation is tetrahedrally coordinated, see: He et al. (2007 ). For the structure of [Ni(terephthalate)(pyrazole)₄], see: Hong et al. (2005 ).

2. Experimental

2.1. Crystal data

[Ni(C₈H₄O₄)(C₁₀H₁₄N₄)(H₂O)]
M_r = 431.09
Monoclinic, P 2₁ /n
a = 11.1603 (7) Å
b = 17.3367 (11) Å
c = 11.2345 (7) Å
β = 116.081 (1)°
V = 1952.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 K
0.28 × 0.18 × 0.15 mm

2.2. Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.645, T_max = 0.746
11758 measured reflections
4236 independent reflections
3627 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.04
4236 reflections
272 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 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—H11⋯O1ⁱ	0.84 (1)	1.80 (2)	2.601 (2)	159 (4)
O1w—H12⋯O4ⁱ	0.84 (1)	1.90 (2)	2.731 (2)	173 (3)
N2—H2⋯O4	0.88 (1)	1.98 (1)	2.837 (2)	164 (2)
N4—H4⋯O4ⁱⁱ	0.87 (1)	2.23 (1)	3.080 (3)	164 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); 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

CCDC reference: 1062289

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015008415/wm5150sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015008415/wm5150Isup2.hkl

checkCIF report

Synthesis and crystallization top

An aqueous mixture of nickel sulfate hexahydrate (52.6 mg, 0.2 mmol), 3,3',5,5'-tetramethyl-4,4'-bipyrazole (38.1 mg, 0.2 mmol) and 1,4-benzene dicarboxylic acid (33.2 mg, 0.2 mmol) was placed in a Teflon-lined, stainless-steel reactor. The reactor was heated to 393 K for 48 hours. It was then cooled to room temperatuer at the rate of 5 K per hour. Green crystals were isolated in 70% yield. C, H, N elemental analysis. Calcd. for C₁₈H₂₀N₄O₅Ni: C 50.15, H 4.68, N 13.00%; found C 50.28, H 4.81, N 12.92%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2 to 1.5 times U_iso(C). The water and amino H-atoms were located in a difference Fourier map, and were refined with distance restraints of O—H 0.84 (1) Å and N—H 0.88 (1) Å; their U_iso(H) parameter were refined independently.

Related literature top

In the related water-free coordination polymer {[Zn(terephthalate)(H₂Bpz)]·0.5(H₂Bpz)}_n (H₂Bpz = 3,3',5,5'-tetramethyl-4,4'-bipyrazole), the Zn²⁺ cation is tetrahedrally coordinated, see: He et al. (2007). For the structure of [Ni(terephthalate)(pyrazole)₄], see: Hong et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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. Displacement ellipsoid plot of a fragment of the three-dimensional network of [Ni(H₂O)(C₁₀H₁₄N₄)(C₈H₄O₄)]_n drawn at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Poly[diaqua(µ₂-benzene-1,4-dicarboxylato-κ²O¹:O⁴)(µ₂-benzene-1,4-dicarboxylato-κ⁴O¹,O^1':O⁴,O^4')bis(µ₂-3,3',5,5'-tetramethyl-4,4'-bipyrazole-κ²N:N')dinickel(II)] top

Crystal data top

[Ni(C₈H₄O₄)(C₁₀H₁₄N₄)(H₂O)]	F(000) = 896
M_r = 431.09	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3721 reflections
a = 11.1603 (7) Å	θ = 2.3–26.7°
b = 17.3367 (11) Å	µ = 1.03 mm⁻¹
c = 11.2345 (7) Å	T = 293 K
β = 116.081 (1)°	Prism, green
V = 1952.3 (2) Å³	0.28 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker SMART diffractometer	4236 independent reflections
Radiation source: fine-focus sealed tube	3627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −13→14
T_min = 0.645, T_max = 0.746	k = −21→22
11758 measured reflections	l = −10→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0583P)² + 0.4664P] where P = (F_o² + 2F_c²)/3
4236 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.40 e Å⁻³
4 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ni(C₈H₄O₄)(C₁₀H₁₄N₄)(H₂O)]	V = 1952.3 (2) Å³
M_r = 431.09	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1603 (7) Å	µ = 1.03 mm⁻¹
b = 17.3367 (11) Å	T = 293 K
c = 11.2345 (7) Å	0.28 × 0.18 × 0.15 mm
β = 116.081 (1)°

Data collection top

Bruker SMART diffractometer	4236 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	3627 reflections with I > 2σ(I)
T_min = 0.645, T_max = 0.746	R_int = 0.027
11758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	4 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.40 e Å⁻³
4236 reflections	Δρ_min = −0.25 e Å⁻³
272 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.36576 (2)	0.277787 (13)	0.18220 (2)	0.01814 (10)
O1	0.19348 (13)	0.32361 (8)	0.02675 (15)	0.0266 (3)
O2	0.29813 (13)	0.38770 (8)	0.21146 (14)	0.0261 (3)
O3	0.40583 (14)	0.17246 (8)	0.12360 (15)	0.0279 (3)
O4	0.21805 (14)	0.11750 (9)	−0.02559 (15)	0.0308 (4)
O1w	0.52381 (16)	0.27350 (9)	0.36205 (17)	0.0316 (4)
H11	0.561 (3)	0.2350 (13)	0.408 (3)	0.068 (11)*
H12	0.580 (2)	0.3083 (13)	0.400 (3)	0.057 (9)*
N1	0.24869 (18)	0.22143 (9)	0.25933 (18)	0.0253 (4)
N2	0.17275 (17)	0.15986 (10)	0.19515 (17)	0.0243 (4)
H2	0.172 (2)	0.1420 (14)	0.1219 (15)	0.034 (7)*
N3	−0.01548 (17)	0.17170 (10)	0.59896 (18)	0.0269 (4)
N4	0.10431 (19)	0.13770 (12)	0.67197 (19)	0.0326 (4)
H4	0.125 (3)	0.1247 (15)	0.7539 (13)	0.044 (8)*
C1	0.20219 (18)	0.38216 (11)	0.0984 (2)	0.0221 (4)
C2	0.09733 (19)	0.44350 (11)	0.0473 (2)	0.0234 (4)
C3	0.0975 (2)	0.50261 (12)	0.1296 (2)	0.0285 (5)
H3	0.1633	0.5043	0.2167	0.034*
C4	0.0006 (2)	0.55935 (12)	0.0835 (2)	0.0285 (5)
H4A	0.0007	0.5990	0.1393	0.034*
C5	0.3431 (2)	0.12127 (11)	0.0413 (2)	0.0241 (4)
C6	0.42497 (19)	0.05760 (12)	0.0211 (2)	0.0234 (4)
C7	0.3661 (2)	−0.01133 (13)	−0.0363 (3)	0.0348 (5)
H7	0.2760	−0.0193	−0.0602	0.042*
C8	0.4405 (2)	−0.06880 (13)	−0.0584 (2)	0.0326 (5)
H8	0.4000	−0.1148	−0.0983	0.039*
C9	0.2976 (3)	0.29163 (17)	0.4676 (3)	0.0512 (8)
H9A	0.3063	0.3368	0.4226	0.077*
H9B	0.3844	0.2748	0.5306	0.077*
H9C	0.2445	0.3036	0.5131	0.077*
C10	0.2318 (2)	0.22909 (12)	0.3692 (2)	0.0289 (5)
C11	0.1447 (2)	0.17158 (12)	0.3746 (2)	0.0262 (4)
C12	0.1100 (2)	0.12834 (12)	0.2614 (2)	0.0261 (4)
C13	0.0226 (2)	0.05878 (14)	0.2117 (3)	0.0408 (6)
H13A	−0.0315	0.0634	0.1180	0.061*
H13B	−0.0339	0.0549	0.2558	0.061*
H13C	0.0771	0.0134	0.2296	0.061*
C14	−0.1337 (3)	0.22052 (18)	0.3690 (3)	0.0508 (8)
H14A	−0.2020	0.2318	0.3964	0.076*
H14B	−0.1677	0.1850	0.2960	0.076*
H14C	−0.1066	0.2673	0.3419	0.076*
C15	−0.0169 (2)	0.18548 (13)	0.4814 (2)	0.0287 (5)
C16	0.1032 (2)	0.16093 (13)	0.4805 (2)	0.0278 (5)
C17	0.1780 (2)	0.13039 (15)	0.6040 (2)	0.0358 (5)
C18	0.3125 (3)	0.0935 (2)	0.6595 (3)	0.0668 (10)
H18A	0.3648	0.1117	0.7481	0.100*
H18B	0.3563	0.1065	0.6053	0.100*
H18C	0.3029	0.0385	0.6606	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01651 (14)	0.01908 (15)	0.01932 (16)	0.00261 (9)	0.00832 (11)	0.00007 (10)
O1	0.0223 (7)	0.0220 (7)	0.0284 (8)	0.0043 (5)	0.0047 (6)	−0.0059 (6)
O2	0.0222 (7)	0.0227 (7)	0.0269 (8)	0.0042 (5)	0.0049 (6)	−0.0023 (6)
O3	0.0311 (8)	0.0217 (7)	0.0331 (9)	0.0056 (6)	0.0161 (7)	−0.0049 (6)
O4	0.0239 (7)	0.0372 (9)	0.0292 (9)	0.0117 (6)	0.0097 (7)	−0.0029 (7)
O1w	0.0261 (8)	0.0268 (9)	0.0284 (9)	−0.0014 (6)	−0.0006 (7)	0.0042 (7)
N1	0.0289 (9)	0.0267 (9)	0.0251 (9)	−0.0038 (7)	0.0162 (8)	−0.0052 (7)
N2	0.0255 (8)	0.0302 (9)	0.0211 (9)	−0.0027 (7)	0.0138 (8)	−0.0041 (7)
N3	0.0248 (9)	0.0342 (10)	0.0237 (9)	0.0024 (7)	0.0126 (8)	0.0008 (8)
N4	0.0358 (10)	0.0439 (11)	0.0248 (11)	0.0133 (8)	0.0195 (9)	0.0087 (9)
C1	0.0194 (9)	0.0201 (10)	0.0258 (11)	0.0013 (7)	0.0090 (8)	0.0001 (8)
C2	0.0191 (9)	0.0208 (10)	0.0276 (11)	0.0029 (7)	0.0076 (8)	0.0001 (8)
C3	0.0241 (10)	0.0278 (11)	0.0249 (11)	0.0054 (8)	0.0027 (9)	−0.0024 (9)
C4	0.0295 (11)	0.0234 (10)	0.0265 (12)	0.0061 (8)	0.0069 (9)	−0.0043 (9)
C5	0.0293 (10)	0.0245 (10)	0.0231 (11)	0.0078 (8)	0.0158 (9)	0.0036 (8)
C6	0.0241 (10)	0.0238 (10)	0.0228 (11)	0.0064 (7)	0.0108 (8)	−0.0019 (8)
C7	0.0207 (10)	0.0328 (12)	0.0516 (15)	0.0008 (8)	0.0166 (10)	−0.0108 (11)
C8	0.0273 (11)	0.0262 (11)	0.0442 (14)	−0.0023 (8)	0.0157 (10)	−0.0132 (10)
C9	0.0678 (19)	0.0585 (17)	0.0416 (16)	−0.0270 (15)	0.0372 (15)	−0.0238 (13)
C10	0.0310 (11)	0.0344 (12)	0.0278 (12)	−0.0031 (9)	0.0190 (10)	−0.0045 (9)
C11	0.0266 (10)	0.0320 (11)	0.0251 (11)	0.0031 (8)	0.0159 (9)	0.0009 (9)
C12	0.0238 (10)	0.0306 (11)	0.0268 (11)	0.0009 (8)	0.0138 (9)	0.0009 (9)
C13	0.0405 (13)	0.0400 (14)	0.0455 (15)	−0.0118 (11)	0.0223 (12)	−0.0045 (11)
C14	0.0406 (15)	0.086 (2)	0.0278 (14)	0.0220 (14)	0.0174 (12)	0.0123 (14)
C15	0.0309 (11)	0.0345 (12)	0.0264 (12)	0.0011 (9)	0.0178 (10)	0.0006 (9)
C16	0.0293 (10)	0.0336 (12)	0.0261 (11)	0.0002 (9)	0.0173 (9)	0.0014 (9)
C17	0.0355 (12)	0.0491 (14)	0.0298 (13)	0.0106 (10)	0.0209 (11)	0.0032 (11)
C18	0.0548 (17)	0.109 (3)	0.0436 (17)	0.0446 (19)	0.0283 (14)	0.0177 (18)

Geometric parameters (Å, º) top

Ni1—O1	2.1036 (14)	C5—C6	1.512 (3)
Ni1—O2	2.1276 (14)	C6—C7	1.380 (3)
Ni1—O3	2.0559 (14)	C6—C8^iv	1.383 (3)
Ni1—O1w	2.0164 (16)	C7—C8	1.388 (3)
Ni1—N1	2.0995 (17)	C7—H7	0.9300
Ni1—N3ⁱ	2.1185 (17)	C8—C6^iv	1.383 (3)
O1—C1	1.273 (2)	C8—H8	0.9300
O2—C1	1.254 (2)	C9—C10	1.491 (3)
O3—C5	1.251 (3)	C9—H9A	0.9600
O4—C5	1.262 (2)	C9—H9B	0.9600
O1w—H11	0.836 (10)	C9—H9C	0.9600
O1w—H12	0.836 (10)	C10—C11	1.412 (3)
N1—C10	1.335 (3)	C11—C12	1.378 (3)
N1—N2	1.357 (2)	C11—C16	1.466 (3)
N2—C12	1.342 (3)	C12—C13	1.496 (3)
N2—H2	0.877 (10)	C13—H13A	0.9600
N3—C15	1.335 (3)	C13—H13B	0.9600
N3—N4	1.358 (2)	C13—H13C	0.9600
N3—Ni1ⁱⁱ	2.1185 (17)	C14—C15	1.489 (3)
N4—C17	1.352 (3)	C14—H14A	0.9600
N4—H4	0.874 (10)	C14—H14B	0.9600
C1—C2	1.497 (3)	C14—H14C	0.9600
C2—C3	1.380 (3)	C15—C16	1.410 (3)
C2—C4ⁱⁱⁱ	1.395 (3)	C16—C17	1.372 (3)
C3—C4	1.383 (3)	C17—C18	1.493 (3)
C3—H3	0.9300	C18—H18A	0.9600
C4—C2ⁱⁱⁱ	1.395 (3)	C18—H18B	0.9600
C4—H4A	0.9300	C18—H18C	0.9600

O1w—Ni1—O3	94.04 (6)	C8^iv—C6—C5	119.95 (19)
O1w—Ni1—N1	89.90 (7)	C6—C7—C8	120.42 (19)
O3—Ni1—N1	88.93 (6)	C6—C7—H7	119.8
O1w—Ni1—O1	157.43 (6)	C8—C7—H7	119.8
O3—Ni1—O1	108.52 (6)	C6^iv—C8—C7	120.0 (2)
N1—Ni1—O1	90.63 (7)	C6^iv—C8—H8	120.0
O1w—Ni1—N3ⁱ	90.92 (7)	C7—C8—H8	120.0
O3—Ni1—N3ⁱ	87.68 (6)	C10—C9—H9A	109.5
N1—Ni1—N3ⁱ	176.55 (7)	C10—C9—H9B	109.5
O1—Ni1—N3ⁱ	89.90 (6)	H9A—C9—H9B	109.5
O1w—Ni1—O2	95.26 (6)	C10—C9—H9C	109.5
O3—Ni1—O2	170.69 (6)	H9A—C9—H9C	109.5
N1—Ni1—O2	91.47 (6)	H9B—C9—H9C	109.5
O1—Ni1—O2	62.17 (5)	N1—C10—C11	110.44 (19)
N3ⁱ—Ni1—O2	91.79 (6)	N1—C10—C9	122.3 (2)
C1—O1—Ni1	89.33 (11)	C11—C10—C9	127.3 (2)
C1—O2—Ni1	88.74 (11)	C12—C11—C10	105.30 (18)
C5—O3—Ni1	137.48 (13)	C12—C11—C16	128.3 (2)
Ni1—O1w—H11	129 (2)	C10—C11—C16	126.3 (2)
Ni1—O1w—H12	127 (2)	N2—C12—C11	106.69 (18)
H11—O1w—H12	102 (3)	N2—C12—C13	122.4 (2)
C10—N1—N2	105.09 (17)	C11—C12—C13	130.9 (2)
C10—N1—Ni1	134.60 (15)	C12—C13—H13A	109.5
N2—N1—Ni1	120.24 (13)	C12—C13—H13B	109.5
C12—N2—N1	112.47 (17)	H13A—C13—H13B	109.5
C12—N2—H2	126.0 (16)	C12—C13—H13C	109.5
N1—N2—H2	121.4 (16)	H13A—C13—H13C	109.5
C15—N3—N4	104.79 (17)	H13B—C13—H13C	109.5
C15—N3—Ni1ⁱⁱ	128.69 (15)	C15—C14—H14A	109.5
N4—N3—Ni1ⁱⁱ	123.63 (14)	C15—C14—H14B	109.5
C17—N4—N3	112.41 (19)	H14A—C14—H14B	109.5
C17—N4—H4	128.6 (18)	C15—C14—H14C	109.5
N3—N4—H4	119.0 (17)	H14A—C14—H14C	109.5
O2—C1—O1	119.70 (17)	H14B—C14—H14C	109.5
O2—C1—C2	120.65 (18)	N3—C15—C16	110.80 (19)
O1—C1—C2	119.65 (18)	N3—C15—C14	122.5 (2)
C3—C2—C4ⁱⁱⁱ	120.16 (18)	C16—C15—C14	126.7 (2)
C3—C2—C1	120.00 (18)	C17—C16—C15	105.50 (19)
C4ⁱⁱⁱ—C2—C1	119.84 (18)	C17—C16—C11	126.9 (2)
C2—C3—C4	120.5 (2)	C15—C16—C11	127.4 (2)
C2—C3—H3	119.8	N4—C17—C16	106.5 (2)
C4—C3—H3	119.8	N4—C17—C18	123.6 (2)
C3—C4—C2ⁱⁱⁱ	119.38 (19)	C16—C17—C18	129.9 (2)
C3—C4—H4A	120.3	C17—C18—H18A	109.5
C2ⁱⁱⁱ—C4—H4A	120.3	C17—C18—H18B	109.5
O3—C5—O4	126.16 (18)	H18A—C18—H18B	109.5
O3—C5—C6	116.72 (18)	C17—C18—H18C	109.5
O4—C5—C6	117.12 (18)	H18A—C18—H18C	109.5
C7—C6—C8^iv	119.55 (19)	H18B—C18—H18C	109.5
C7—C6—C5	120.49 (18)

O1w—Ni1—O1—C1	−1.3 (2)	Ni1—O3—C5—C6	170.67 (14)
O3—Ni1—O1—C1	178.98 (11)	O3—C5—C6—C7	161.3 (2)
N1—Ni1—O1—C1	89.91 (12)	O4—C5—C6—C7	−18.2 (3)
N3ⁱ—Ni1—O1—C1	−93.50 (12)	O3—C5—C6—C8^iv	−19.8 (3)
O2—Ni1—O1—C1	−1.42 (11)	O4—C5—C6—C8^iv	160.8 (2)
O1w—Ni1—O2—C1	−178.52 (12)	C8^iv—C6—C7—C8	−0.9 (4)
O3—Ni1—O2—C1	3.8 (4)	C5—C6—C7—C8	178.0 (2)
N1—Ni1—O2—C1	−88.49 (12)	C6—C7—C8—C6^iv	0.9 (4)
O1—Ni1—O2—C1	1.45 (11)	N2—N1—C10—C11	0.2 (2)
N3ⁱ—Ni1—O2—C1	90.39 (12)	Ni1—N1—C10—C11	−176.44 (15)
O1w—Ni1—O3—C5	157.3 (2)	N2—N1—C10—C9	−179.1 (2)
N1—Ni1—O3—C5	67.5 (2)	Ni1—N1—C10—C9	4.2 (4)
O1—Ni1—O3—C5	−22.8 (2)	N1—C10—C11—C12	0.2 (3)
N3ⁱ—Ni1—O3—C5	−112.0 (2)	C9—C10—C11—C12	179.5 (3)
O2—Ni1—O3—C5	−25.1 (5)	N1—C10—C11—C16	179.4 (2)
O1w—Ni1—N1—C10	44.9 (2)	C9—C10—C11—C16	−1.3 (4)
O3—Ni1—N1—C10	138.9 (2)	N1—N2—C12—C11	0.7 (2)
O1—Ni1—N1—C10	−112.6 (2)	N1—N2—C12—C13	−178.74 (19)
N3ⁱ—Ni1—N1—C10	148.7 (11)	C10—C11—C12—N2	−0.5 (2)
O2—Ni1—N1—C10	−50.4 (2)	C16—C11—C12—N2	−179.7 (2)
O1w—Ni1—N1—N2	−131.40 (15)	C10—C11—C12—C13	178.9 (2)
O3—Ni1—N1—N2	−37.35 (15)	C16—C11—C12—C13	−0.4 (4)
O1—Ni1—N1—N2	71.16 (15)	N4—N3—C15—C16	−0.7 (2)
N3ⁱ—Ni1—N1—N2	−27.6 (12)	Ni1ⁱⁱ—N3—C15—C16	160.26 (15)
O2—Ni1—N1—N2	133.34 (15)	N4—N3—C15—C14	178.0 (2)
C10—N1—N2—C12	−0.6 (2)	Ni1ⁱⁱ—N3—C15—C14	−21.1 (3)
Ni1—N1—N2—C12	176.69 (14)	N3—C15—C16—C17	0.7 (3)
C15—N3—N4—C17	0.5 (3)	C14—C15—C16—C17	−177.9 (3)
Ni1ⁱⁱ—N3—N4—C17	−161.73 (17)	N3—C15—C16—C11	−174.6 (2)
Ni1—O2—C1—O1	−2.43 (19)	C14—C15—C16—C11	6.8 (4)
Ni1—O2—C1—C2	177.19 (17)	C12—C11—C16—C17	103.9 (3)
Ni1—O1—C1—O2	2.46 (19)	C10—C11—C16—C17	−75.2 (3)
Ni1—O1—C1—C2	−177.17 (17)	C12—C11—C16—C15	−81.9 (3)
O2—C1—C2—C3	−7.0 (3)	C10—C11—C16—C15	99.1 (3)
O1—C1—C2—C3	172.62 (19)	N3—N4—C17—C16	0.0 (3)
O2—C1—C2—C4ⁱⁱⁱ	173.1 (2)	N3—N4—C17—C18	−178.6 (3)
O1—C1—C2—C4ⁱⁱⁱ	−7.2 (3)	C15—C16—C17—N4	−0.4 (3)
C4ⁱⁱⁱ—C2—C3—C4	0.2 (4)	C11—C16—C17—N4	174.9 (2)
C1—C2—C3—C4	−179.6 (2)	C15—C16—C17—C18	178.1 (3)
C2—C3—C4—C2ⁱⁱⁱ	−0.2 (4)	C11—C16—C17—C18	−6.6 (5)
Ni1—O3—C5—O4	−9.9 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O1^v	0.84 (1)	1.80 (2)	2.601 (2)	159 (4)
O1w—H12···O4^v	0.84 (1)	1.90 (2)	2.731 (2)	173 (3)
N2—H2···O4	0.88 (1)	1.98 (1)	2.837 (2)	164 (2)
N4—H4···O4^vi	0.87 (1)	2.23 (1)	3.080 (3)	164 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O1ⁱ	0.84 (1)	1.80 (2)	2.601 (2)	159 (4)
O1w—H12···O4ⁱ	0.84 (1)	1.90 (2)	2.731 (2)	173 (3)
N2—H2···O4	0.88 (1)	1.98 (1)	2.837 (2)	164 (2)
N4—H4···O4ⁱⁱ	0.87 (1)	2.23 (1)	3.080 (3)	164 (2)

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

Acknowledgements

The authors acknowledge Guangdong University of Technology for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 71| Part 6| June 2015| Pages m127-m128

doi:10.1107/S2056989015008415

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