Propane-1,2-diammonium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O')nickelate(II) tetra-hydrate.

The reaction of nickel(II) nitrate hexa-hydrate, propane-1,2-diamine and pyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in aqueous solution resulted in the formation of the title compound, (C(3)H(12)N(2))[Ni(C(7)H(3)NO(4))(2)]·4H(2)O or (p-1,2-daH(2))[Ni(pydc)(2)]·4H(2)O (where p-1,2-da is propane-1,2-diamine and pydcH(2) is pyridine-2,6-dicarboxylic acid). The geometry of the resulting NiN(2)O(4) coordination can be described as distorted octa-hedral. Considerable C=O⋯π stacking inter-actions are observed between the carboxyl-ate C=O groups and the pyridine rings of the (pydc)(2-) fragments, with O⋯π distances of 3.1563 (12) and 3.2523 (12) Å and C=O⋯π angles of 95.14 (8) and 94.64 (8)°. In the crystal structure, a wide range of non-covalent inter-actions, consisting of hydrogen bonding [O-H⋯O, N-H⋯O and C-H⋯O, with D⋯A distances ranging from 2.712 (2) to 3.484 (2) Å], ion pairing, π-π [centroid-to-centroid distance = 3.4825 (8) Å] and C=O⋯π stacking, connect the various components to form a supra-molecular structure.

Related literature

For related literature, see: Aghabozorg et al. (2007 ▶); Aghabozorg, Ghadermazi & Attar Gharamaleki (2006 ▶); Aghabozorg, Ghadermazi & Ramezanipour (2006 ▶); Aghabozorg, Heidari et al. (2008 ▶); Aghabozorg, Manteghi & Sheshmani (2008 ▶).

Experimental

Crystal data

(C3H12N2)[Ni(C7H3NO4)2]·4H2O

M = 537.13

Orthorhombic,

a = 20.7598 (6) Å

b = 8.2582 (2) Å

c = 12.7242 (4) Å

V = 2181.42 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.96 mm−1

T = 100 (2) K

0.26 × 0.22 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.781, T max = 0.898

36654 measured reflections

6379 independent reflections

6016 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.059

S = 1.01

6379 reflections

310 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 2846 Friedel pairs

Flack parameter: 0.004 (7)

Data collection: APEX2 (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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016309/su2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016309/su2054Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C3H12N2)[Ni(C7H3NO4)2]·4H2O	F000 = 1120
Mr = 537.13	Dx = 1.635 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 410 reflections
a = 20.7598 (6) Å	θ = 3–29º
b = 8.2582 (2) Å	µ = 0.96 mm−1
c = 12.7242 (4) Å	T = 100 (2) K
V = 2181.42 (11) Å3	Prism, light-green
Z = 4	0.26 × 0.22 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	6379 independent reflections
Radiation source: fine-focus sealed tube	6016 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 100(2) K	θmax = 30.0º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −29→29
Tmin = 0.781, Tmax = 0.898	k = −11→11
36654 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.023	w = 1/[σ2(Fo2) + (0.03P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.059	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.34 e Å−3
6379 reflections	Δρmin = −0.33 e Å−3
310 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.004 (7)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Ni1	0.230880 (7)	0.50781 (2)	0.25665 (2)	0.00841 (4)
O1	0.36657 (5)	0.27840 (12)	0.44207 (8)	0.0123 (2)
O2	0.30848 (5)	0.35043 (12)	0.30169 (8)	0.0110 (2)
O3	0.15872 (5)	0.68763 (13)	0.28120 (8)	0.0131 (2)
O4	0.10593 (5)	0.81657 (13)	0.41025 (9)	0.0133 (2)
O5	0.35128 (5)	0.74395 (13)	0.04995 (8)	0.0128 (2)
O6	0.30178 (5)	0.66991 (13)	0.19960 (8)	0.0113 (2)
O7	0.15889 (5)	0.32530 (12)	0.24551 (9)	0.0120 (2)
O8	0.09570 (5)	0.20477 (13)	0.12645 (9)	0.0146 (2)
N1	0.23302 (5)	0.53498 (17)	0.41041 (11)	0.0085 (2)
N2	0.22246 (6)	0.48264 (15)	0.10356 (12)	0.0090 (3)
C1	0.27701 (7)	0.45504 (17)	0.46722 (12)	0.0087 (2)
C2	0.28041 (8)	0.47344 (19)	0.57519 (13)	0.0109 (3)
H2A	0.3120	0.4178	0.6153	0.013*
C3	0.23594 (7)	0.57630 (18)	0.62343 (12)	0.0112 (3)
H3A	0.2371	0.5909	0.6975	0.013*
C4	0.18997 (7)	0.65754 (17)	0.56366 (11)	0.0102 (3)
H4A	0.1593	0.7270	0.5958	0.012*
C5	0.19040 (7)	0.63384 (17)	0.45558 (11)	0.0088 (2)
C6	0.32098 (6)	0.35197 (16)	0.39952 (12)	0.0096 (2)
C7	0.14761 (7)	0.71970 (17)	0.37710 (11)	0.0102 (3)
C8	0.26305 (6)	0.56135 (18)	0.04015 (12)	0.0095 (3)
C9	0.26076 (7)	0.5380 (2)	−0.06858 (12)	0.0105 (3)
H9A	0.2901	0.5919	−0.1140	0.013*
C10	0.21417 (7)	0.43328 (18)	−0.10826 (11)	0.0121 (3)
H10A	0.2116	0.4147	−0.1818	0.015*
C11	0.17109 (7)	0.35526 (17)	−0.04071 (12)	0.0110 (3)
H11A	0.1385	0.2857	−0.0673	0.013*
C12	0.17748 (6)	0.38260 (17)	0.06599 (12)	0.0097 (2)
C13	0.30969 (6)	0.66803 (17)	0.10021 (12)	0.0101 (3)
C14	0.14033 (7)	0.29812 (17)	0.15243 (12)	0.0108 (3)
N3	0.54006 (6)	0.43977 (15)	0.30200 (10)	0.0123 (2)
H3B	0.5651	0.5201	0.3289	0.018*
H3C	0.5010	0.4809	0.2837	0.018*
H3D	0.5595	0.3971	0.2442	0.018*
N4	0.44676 (5)	0.16524 (15)	0.27970 (10)	0.0118 (2)
H4B	0.4502	0.2393	0.2270	0.018*
H4C	0.4162	0.1982	0.3263	0.018*
H4D	0.4354	0.0676	0.2523	0.018*
C15	0.53120 (7)	0.31041 (17)	0.38271 (12)	0.0130 (3)
H15A	0.4983	0.3459	0.4340	0.016*
H15B	0.5722	0.2949	0.4212	0.016*
C16	0.51052 (7)	0.14977 (17)	0.33504 (12)	0.0113 (2)
H16A	0.5437	0.1154	0.2827	0.014*
C17	0.50526 (8)	0.01962 (18)	0.41937 (13)	0.0174 (3)
H17A	0.4940	−0.0840	0.3866	0.026*
H17B	0.4718	0.0499	0.4700	0.026*
H17C	0.5466	0.0091	0.4558	0.026*
O1W	0.42220 (5)	0.59529 (14)	0.30653 (9)	0.0169 (2)
H1WA	0.4295	0.6786	0.2735	0.020*
H1WB	0.3837	0.5823	0.2945	0.020*
O2W	0.06395 (6)	0.74698 (19)	0.13415 (10)	0.0297 (3)
H2WA	0.0821	0.6693	0.1612	0.036*
H2WB	0.0882	0.7755	0.0867	0.036*
O3W	−0.03481 (5)	0.15335 (15)	0.09506 (9)	0.0199 (2)
H3WA	0.0027	0.1743	0.0800	0.024*
H3WB	−0.0520	0.1482	0.0372	0.024*
O4W	0.44262 (5)	0.86620 (13)	0.18005 (9)	0.0158 (2)
H4WA	0.4731	0.8280	0.1474	0.019*
H4WB	0.4180	0.8294	0.1357	0.019*

	U11	U22	U33	U12	U13	U23
Ni1	0.00786 (7)	0.01104 (7)	0.00634 (7)	0.00044 (6)	−0.00030 (7)	−0.00050 (7)
O1	0.0097 (4)	0.0146 (5)	0.0125 (5)	0.0032 (4)	−0.0006 (4)	0.0011 (4)
O2	0.0123 (4)	0.0127 (5)	0.0082 (5)	0.0015 (4)	−0.0003 (4)	−0.0013 (4)
O3	0.0121 (5)	0.0174 (5)	0.0097 (5)	0.0037 (4)	−0.0006 (4)	0.0003 (4)
O4	0.0125 (5)	0.0146 (5)	0.0129 (5)	0.0047 (4)	0.0020 (4)	0.0016 (4)
O5	0.0110 (5)	0.0154 (5)	0.0121 (5)	−0.0025 (4)	0.0019 (4)	−0.0005 (4)
O6	0.0106 (5)	0.0139 (5)	0.0092 (5)	−0.0009 (4)	−0.0003 (4)	−0.0009 (4)
O7	0.0115 (4)	0.0165 (4)	0.0081 (5)	−0.0015 (3)	0.0002 (4)	0.0010 (4)
O8	0.0131 (5)	0.0173 (5)	0.0134 (5)	−0.0049 (4)	−0.0003 (4)	−0.0013 (4)
N1	0.0095 (6)	0.0079 (5)	0.0080 (6)	−0.0005 (4)	−0.0004 (4)	−0.0014 (5)
N2	0.0081 (5)	0.0099 (5)	0.0088 (6)	0.0014 (4)	0.0000 (5)	0.0009 (5)
C1	0.0084 (6)	0.0083 (6)	0.0095 (6)	−0.0008 (5)	−0.0002 (5)	0.0010 (5)
C2	0.0123 (6)	0.0093 (6)	0.0111 (7)	−0.0004 (5)	−0.0004 (5)	0.0009 (5)
C3	0.0136 (6)	0.0122 (6)	0.0080 (6)	−0.0017 (5)	0.0010 (5)	−0.0003 (5)
C4	0.0106 (6)	0.0110 (6)	0.0090 (6)	−0.0010 (5)	0.0032 (5)	−0.0012 (5)
C5	0.0074 (6)	0.0098 (6)	0.0094 (6)	−0.0007 (5)	0.0001 (5)	0.0019 (5)
C6	0.0084 (6)	0.0084 (6)	0.0121 (6)	−0.0010 (4)	0.0012 (5)	−0.0001 (5)
C7	0.0090 (6)	0.0102 (6)	0.0114 (6)	−0.0010 (5)	−0.0005 (5)	0.0012 (5)
C8	0.0080 (6)	0.0096 (6)	0.0108 (7)	0.0008 (5)	0.0000 (5)	−0.0010 (5)
C9	0.0135 (6)	0.0098 (6)	0.0081 (7)	0.0006 (5)	0.0003 (5)	0.0022 (5)
C10	0.0171 (7)	0.0122 (6)	0.0071 (6)	0.0015 (5)	−0.0011 (5)	−0.0013 (5)
C11	0.0112 (6)	0.0105 (6)	0.0112 (6)	0.0007 (5)	−0.0015 (5)	−0.0004 (5)
C12	0.0073 (6)	0.0098 (6)	0.0121 (6)	0.0011 (5)	0.0001 (5)	−0.0004 (5)
C13	0.0083 (6)	0.0096 (6)	0.0125 (6)	0.0015 (5)	−0.0007 (5)	−0.0010 (5)
C14	0.0088 (6)	0.0116 (6)	0.0119 (6)	0.0010 (5)	0.0022 (5)	0.0001 (5)
N3	0.0108 (5)	0.0121 (5)	0.0141 (6)	−0.0006 (4)	−0.0012 (4)	−0.0033 (5)
N4	0.0106 (5)	0.0127 (5)	0.0122 (6)	0.0001 (4)	−0.0016 (4)	−0.0010 (4)
C15	0.0127 (6)	0.0143 (6)	0.0119 (6)	−0.0011 (5)	−0.0011 (5)	−0.0020 (5)
C16	0.0099 (6)	0.0127 (6)	0.0113 (6)	0.0003 (5)	−0.0007 (5)	−0.0006 (5)
C17	0.0204 (7)	0.0153 (7)	0.0164 (7)	0.0027 (5)	−0.0024 (6)	0.0026 (6)
O1W	0.0118 (5)	0.0196 (5)	0.0193 (6)	0.0011 (4)	−0.0009 (4)	0.0034 (4)
O2W	0.0140 (5)	0.0595 (9)	0.0155 (6)	−0.0035 (6)	−0.0019 (4)	0.0121 (6)
O3W	0.0142 (5)	0.0318 (6)	0.0138 (5)	0.0009 (5)	−0.0037 (4)	−0.0011 (5)
O4W	0.0139 (5)	0.0171 (5)	0.0163 (5)	−0.0014 (4)	−0.0006 (4)	−0.0047 (4)

Ni1—N2	1.9668 (15)	C9—H9A	0.9500
Ni1—N1	1.9698 (14)	C10—C11	1.398 (2)
Ni1—O6	2.1178 (11)	C10—H10A	0.9500
Ni1—O7	2.1273 (10)	C11—C12	1.383 (2)
Ni1—O3	2.1324 (10)	C11—H11A	0.9500
Ni1—O2	2.1477 (10)	C12—C14	1.514 (2)
O1—C6	1.2483 (17)	N3—C15	1.4932 (19)
O2—C6	1.2717 (18)	N3—H3B	0.9100
O3—C7	1.2697 (18)	N3—H3C	0.9100
O4—C7	1.2516 (17)	N3—H3D	0.9100
O5—C13	1.2441 (18)	N4—C16	1.5048 (17)
O6—C13	1.2754 (19)	N4—H4B	0.9100
O7—C14	1.2655 (19)	N4—H4C	0.9100
O8—C14	1.2498 (18)	N4—H4D	0.9100
N1—C5	1.3340 (19)	C15—C16	1.5205 (19)
N1—C1	1.3387 (19)	C15—H15A	0.9900
N2—C12	1.335 (2)	C15—H15B	0.9900
N2—C8	1.335 (2)	C16—C17	1.523 (2)
C1—C2	1.384 (2)	C16—H16A	1.0000
C1—C6	1.516 (2)	C17—H17A	0.9800
C2—C3	1.397 (2)	C17—H17B	0.9800
C2—H2A	0.9500	C17—H17C	0.9800
C3—C4	1.393 (2)	O1W—H1WA	0.8201
C3—H3A	0.9500	O1W—H1WB	0.8200
C4—C5	1.389 (2)	O2W—H2WA	0.8201
C4—H4A	0.9500	O2W—H2WB	0.8198
C5—C7	1.5130 (19)	O3W—H3WA	0.8200
C8—C9	1.398 (2)	O3W—H3WB	0.8201
C8—C13	1.516 (2)	O4W—H4WA	0.8201
C9—C10	1.392 (2)	O4W—H4WB	0.8201
N2—Ni1—N1	176.17 (5)	C8—C9—H9A	121.0
N2—Ni1—O6	77.83 (5)	C9—C10—C11	120.52 (14)
N1—Ni1—O6	104.64 (5)	C9—C10—H10A	119.7
N2—Ni1—O7	78.27 (5)	C11—C10—H10A	119.7
N1—Ni1—O7	99.37 (5)	C12—C11—C10	117.85 (14)
O6—Ni1—O7	155.96 (4)	C12—C11—H11A	121.1
N2—Ni1—O3	98.99 (5)	C10—C11—H11A	121.1
N1—Ni1—O3	77.94 (5)	N2—C12—C11	121.31 (14)
O6—Ni1—O3	95.64 (4)	N2—C12—C14	112.42 (14)
O7—Ni1—O3	90.55 (4)	C11—C12—C14	126.11 (13)
N2—Ni1—O2	105.48 (5)	O5—C13—O6	126.37 (14)
N1—Ni1—O2	77.70 (5)	O5—C13—C8	118.49 (13)
O6—Ni1—O2	87.29 (4)	O6—C13—C8	115.14 (12)
O7—Ni1—O2	96.66 (4)	O8—C14—O7	125.63 (14)
O3—Ni1—O2	155.41 (4)	O8—C14—C12	118.02 (13)
C6—O2—Ni1	114.09 (9)	O7—C14—C12	116.31 (12)
C7—O3—Ni1	114.43 (9)	C15—N3—H3B	109.5
C13—O6—Ni1	114.94 (9)	C15—N3—H3C	109.5
C14—O7—Ni1	113.70 (9)	H3B—N3—H3C	109.5
C5—N1—C1	121.44 (14)	C15—N3—H3D	109.5
C5—N1—Ni1	118.86 (10)	H3B—N3—H3D	109.5
C1—N1—Ni1	119.70 (10)	H3C—N3—H3D	109.5
C12—N2—C8	121.75 (15)	C16—N4—H4B	109.5
C12—N2—Ni1	118.82 (11)	C16—N4—H4C	109.5
C8—N2—Ni1	119.39 (11)	H4B—N4—H4C	109.5
N1—C1—C2	121.11 (14)	C16—N4—H4D	109.5
N1—C1—C6	112.38 (13)	H4B—N4—H4D	109.5
C2—C1—C6	126.50 (14)	H4C—N4—H4D	109.5
C1—C2—C3	117.99 (14)	N3—C15—C16	112.62 (12)
C1—C2—H2A	121.0	N3—C15—H15A	109.1
C3—C2—H2A	121.0	C16—C15—H15A	109.1
C4—C3—C2	120.40 (14)	N3—C15—H15B	109.1
C4—C3—H3A	119.8	C16—C15—H15B	109.1
C2—C3—H3A	119.8	H15A—C15—H15B	107.8
C5—C4—C3	117.93 (13)	N4—C16—C15	111.16 (11)
C5—C4—H4A	121.0	N4—C16—C17	109.06 (12)
C3—C4—H4A	121.0	C15—C16—C17	110.80 (12)
N1—C5—C4	121.13 (14)	N4—C16—H16A	108.6
N1—C5—C7	113.07 (13)	C15—C16—H16A	108.6
C4—C5—C7	125.70 (13)	C17—C16—H16A	108.6
O1—C6—O2	125.06 (13)	C16—C17—H17A	109.5
O1—C6—C1	118.90 (13)	C16—C17—H17B	109.5
O2—C6—C1	116.03 (12)	H17A—C17—H17B	109.5
O4—C7—O3	125.65 (13)	C16—C17—H17C	109.5
O4—C7—C5	118.88 (13)	H17A—C17—H17C	109.5
O3—C7—C5	115.46 (12)	H17B—C17—H17C	109.5
N2—C8—C9	120.62 (14)	H1WA—O1W—H1WB	101.2
N2—C8—C13	112.42 (13)	H2WA—O2W—H2WB	104.5
C9—C8—C13	126.95 (13)	H3WA—O3W—H3WB	102.4
C10—C9—C8	117.93 (14)	H4WA—O4W—H4WB	89.5
C10—C9—H9A	121.0
N2—Ni1—O2—C6	179.68 (10)	Ni1—N1—C5—C4	−179.84 (10)
N1—Ni1—O2—C6	−2.52 (10)	C1—N1—C5—C7	176.61 (12)
O6—Ni1—O2—C6	103.10 (10)	Ni1—N1—C5—C7	−3.14 (16)
O7—Ni1—O2—C6	−100.70 (10)	C3—C4—C5—N1	0.7 (2)
O3—Ni1—O2—C6	5.46 (16)	C3—C4—C5—C7	−175.52 (13)
N2—Ni1—O3—C7	173.26 (10)	Ni1—O2—C6—O1	−175.13 (11)
N1—Ni1—O3—C7	−4.41 (10)	Ni1—O2—C6—C1	3.57 (15)
O6—Ni1—O3—C7	−108.21 (10)	N1—C1—C6—O1	175.89 (13)
O7—Ni1—O3—C7	95.05 (10)	C2—C1—C6—O1	−2.4 (2)
O2—Ni1—O3—C7	−12.39 (16)	N1—C1—C6—O2	−2.89 (18)
N2—Ni1—O6—C13	−4.98 (10)	C2—C1—C6—O2	178.85 (14)
N1—Ni1—O6—C13	178.04 (10)	Ni1—O3—C7—O4	−177.39 (11)
O7—Ni1—O6—C13	1.20 (16)	Ni1—O3—C7—C5	4.04 (15)
O3—Ni1—O6—C13	−102.99 (10)	N1—C5—C7—O4	−179.55 (13)
O2—Ni1—O6—C13	101.50 (10)	C4—C5—C7—O4	−3.0 (2)
N2—Ni1—O7—C14	−6.39 (10)	N1—C5—C7—O3	−0.87 (18)
N1—Ni1—O7—C14	170.54 (10)	C4—C5—C7—O3	175.64 (13)
O6—Ni1—O7—C14	−12.55 (15)	C12—N2—C8—C9	−1.7 (2)
O3—Ni1—O7—C14	92.68 (10)	Ni1—N2—C8—C9	176.03 (11)
O2—Ni1—O7—C14	−110.88 (10)	C12—N2—C8—C13	179.89 (12)
O6—Ni1—N1—C5	96.77 (11)	Ni1—N2—C8—C13	−2.41 (16)
O7—Ni1—N1—C5	−84.54 (11)	N2—C8—C9—C10	1.3 (2)
O3—Ni1—N1—C5	4.01 (11)	C13—C8—C9—C10	179.52 (14)
O2—Ni1—N1—C5	−179.38 (12)	C8—C9—C10—C11	0.3 (2)
O6—Ni1—N1—C1	−83.00 (12)	C9—C10—C11—C12	−1.6 (2)
O7—Ni1—N1—C1	95.70 (11)	C8—N2—C12—C11	0.3 (2)
O3—Ni1—N1—C1	−175.75 (12)	Ni1—N2—C12—C11	−177.38 (10)
O2—Ni1—N1—C1	0.86 (11)	C8—N2—C12—C14	175.92 (12)
O6—Ni1—N2—C12	−178.35 (11)	Ni1—N2—C12—C14	−1.80 (16)
O7—Ni1—N2—C12	4.21 (10)	C10—C11—C12—N2	1.3 (2)
O3—Ni1—N2—C12	−84.47 (11)	C10—C11—C12—C14	−173.67 (13)
O2—Ni1—N2—C12	97.96 (11)	Ni1—O6—C13—O5	−174.76 (11)
O6—Ni1—N2—C8	3.88 (10)	Ni1—O6—C13—C8	5.13 (15)
O7—Ni1—N2—C8	−173.56 (11)	N2—C8—C13—O5	177.84 (12)
O3—Ni1—N2—C8	97.75 (11)	C9—C8—C13—O5	−0.5 (2)
O2—Ni1—N2—C8	−79.81 (11)	N2—C8—C13—O6	−2.06 (18)
C5—N1—C1—C2	−0.8 (2)	C9—C8—C13—O6	179.62 (14)
Ni1—N1—C1—C2	179.00 (11)	Ni1—O7—C14—O8	−174.94 (12)
C5—N1—C1—C6	−179.12 (12)	Ni1—O7—C14—C12	7.30 (15)
Ni1—N1—C1—C6	0.63 (16)	N2—C12—C14—O8	178.05 (12)
N1—C1—C2—C3	0.9 (2)	C11—C12—C14—O8	−6.6 (2)
C6—C1—C2—C3	179.00 (13)	N2—C12—C14—O7	−4.02 (18)
C1—C2—C3—C4	−0.2 (2)	C11—C12—C14—O7	171.32 (14)
C2—C3—C4—C5	−0.6 (2)	N3—C15—C16—N4	−61.32 (15)
C1—N1—C5—C4	−0.1 (2)	N3—C15—C16—C17	177.24 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4W	0.82	1.97	2.788 (2)	173
O1W—H1WB···O2	0.82	2.47	3.109 (2)	135
O1W—H1WB···O6	0.82	2.21	2.912 (2)	144
O2W—H2WA···O3	0.82	2.21	2.759 (2)	125
N3—H3B···O4i	0.91	1.90	2.795 (2)	168
N3—H3C···O1W	0.91	1.91	2.763 (2)	155
N3—H3D···O8ii	0.91	1.88	2.783 (2)	176
O2W—H2WB···O1iii	0.82	2.07	2.849 (2)	160
N4—H4B···O3Wii	0.91	1.92	2.812 (2)	165
N4—H4C···O1	0.91	1.92	2.813 (2)	168
N4—H4D···O4Wiv	0.91	1.91	2.777 (2)	160
O3W—H3WA···O8	0.82	2.03	2.771 (2)	149
O3W—H3WB···O4v	0.82	1.99	2.787 (2)	166
O4W—H4WA···O2Wi	0.82	1.99	2.749 (2)	153
O4W—H4WB···O5	0.82	1.90	2.712 (2)	171
C10—H10A···O6vi	0.95	2.54	3.289 (2)	136
C11—H11A···O1Wvi	0.95	2.58	3.484 (2)	160
C15—H15B···O5vii	0.99	2.30	3.268 (2)	164
C16—H16A···O7ii	1.00	2.49	3.291 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4W	0.82	1.97	2.788 (2)	173
O1W—H1WB⋯O2	0.82	2.47	3.109 (2)	135
O1W—H1WB⋯O6	0.82	2.21	2.912 (2)	144
O2W—H2WA⋯O3	0.82	2.21	2.759 (2)	125
N3—H3B⋯O4i	0.91	1.90	2.795 (2)	168
N3—H3C⋯O1W	0.91	1.91	2.763 (2)	155
N3—H3D⋯O8ii	0.91	1.88	2.783 (2)	176
O2W—H2WB⋯O1iii	0.82	2.07	2.849 (2)	160
N4—H4B⋯O3Wii	0.91	1.92	2.812 (2)	165
N4—H4C⋯O1	0.91	1.92	2.813 (2)	168
N4—H4D⋯O4Wiv	0.91	1.91	2.777 (2)	160
O3W—H3WA⋯O8	0.82	2.03	2.771 (2)	149
O3W—H3WB⋯O4v	0.82	1.99	2.787 (2)	166
O4W—H4WA⋯O2Wi	0.82	1.99	2.749 (2)	153
O4W—H4WB⋯O5	0.82	1.90	2.712 (2)	171
C10—H10A⋯O6vi	0.95	2.54	3.289 (2)	136
C11—H11A⋯O1Wvi	0.95	2.58	3.484 (2)	160
C15—H15B⋯O5vii	0.99	2.30	3.268 (2)	164
C16—H16A⋯O7ii	1.00	2.49	3.291 (2)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .