Hydroxonium creatininium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)nickel-ate(II) trihydrate.

The title compound, (C(4)H(8)N(3)O)(H(3)O)[Ni(C(7)H(3)NO(4))(2)]·3H(2)O, exhibits isotypism with its Co(II) analogue. All intramolecular distances and angles are similar for the two structures. This applies also for the intermolecular forces, consisting of O-H⋯O and N-H⋯O hydrogen bonds and π-π interactions [with centroid-centroid distances of 3.428 (2) and 3.579 (2) Å], that lead to a cohesion of the structure.

Related literature

For background to proton-transfer agents, see: Aghabozorg, Manteghi et al. (2008 ▶); Soleimannejad et al. (2005 ▶); Aghabozorg, Ramezanipour et al. (2008 ▶). For related structures, see: Moghimi et al. (2004 ▶, 2005 ▶); Aghabozorg, Motyeian et al. (2008 ▶); Aghabozorg, Derikvand et al. (2008 ▶). For the isotypic Co compound, see: Aghabozorg et al. (2009 ▶).

Experimental

Crystal data

(C4H8N3O)(H3O)[Ni(C7H3NO4)2]·3H2O

M = 576.12

Triclinic,

a = 8.1466 (9) Å

b = 10.7420 (12) Å

c = 13.5061 (15) Å

α = 74.890 (2)°

β = 89.944 (2)°

γ = 87.564 (3)°

V = 1140.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 120 K

0.18 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.803, T max = 0.896

11509 measured reflections

5404 independent reflections

3827 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.134

S = 1.00

5404 reflections

335 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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/S1600536809022053/pv2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022053/pv2161Isup2.hkl

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

(C4H8N3O)(H3O)[Ni(C7H3NO4)2]·3H2O	Z = 2
Mr = 576.12	F(000) = 596
Triclinic, P1	Dx = 1.678 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1466 (9) Å	Cell parameters from 1838 reflections
b = 10.7420 (12) Å	θ = 2.8–24.2°
c = 13.5061 (15) Å	µ = 0.93 mm−1
α = 74.890 (2)°	T = 120 K
β = 89.944 (2)°	Prism, green
γ = 87.564 (3)°	0.18 × 0.14 × 0.12 mm
V = 1140.0 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	5404 independent reflections
Radiation source: fine-focus sealed tube	3827 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.803, Tmax = 0.896	k = −14→14
11509 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: mixed
wR(F2) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0405P)2 + 2.37P] where P = (Fo2 + 2Fc2)/3
5404 reflections	(Δ/σ)max = 0.001
335 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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	0.26883 (5)	0.07342 (4)	0.22939 (3)	0.01905 (13)
O1	0.4241 (3)	−0.0881 (2)	0.23014 (17)	0.0225 (5)
O2	0.4819 (3)	−0.2302 (2)	0.13848 (18)	0.0245 (5)
O3	0.0829 (3)	0.2229 (2)	0.16633 (17)	0.0211 (5)
O4	−0.0572 (3)	0.3100 (2)	0.01983 (17)	0.0254 (5)
O5	0.4573 (3)	0.2152 (2)	0.18788 (17)	0.0220 (5)
O6	0.6101 (3)	0.3404 (2)	0.25748 (18)	0.0271 (5)
O7	0.1100 (3)	−0.0493 (2)	0.33115 (17)	0.0228 (5)
O8	0.0881 (3)	−0.1386 (2)	0.50037 (18)	0.0271 (5)
N1	0.2282 (3)	0.0494 (2)	0.0918 (2)	0.0165 (5)
N2	0.3261 (3)	0.1077 (2)	0.3616 (2)	0.0161 (5)
C1	0.3098 (4)	−0.0458 (3)	0.0640 (2)	0.0175 (6)
C2	0.2950 (4)	−0.0601 (3)	−0.0352 (2)	0.0201 (7)
H2A	0.3515	−0.1291	−0.0547	0.024*
C3	0.1952 (4)	0.0295 (3)	−0.1048 (3)	0.0221 (7)
H3A	0.1842	0.0227	−0.1732	0.027*
C4	0.1118 (4)	0.1285 (3)	−0.0749 (2)	0.0208 (7)
H4A	0.0440	0.1904	−0.1221	0.025*
C5	0.1297 (4)	0.1347 (3)	0.0252 (2)	0.0174 (6)
C6	0.4140 (4)	−0.1286 (3)	0.1508 (2)	0.0189 (7)
C7	0.0456 (4)	0.2315 (3)	0.0738 (2)	0.0203 (7)
C8	0.4375 (4)	0.1947 (3)	0.3651 (2)	0.0175 (6)
C9	0.4809 (4)	0.2192 (3)	0.4569 (2)	0.0207 (7)
H9A	0.5607	0.2803	0.4591	0.025*
C10	0.4039 (4)	0.1512 (3)	0.5470 (2)	0.0212 (7)
H10A	0.4291	0.1671	0.6112	0.025*
C11	0.2910 (4)	0.0610 (3)	0.5404 (2)	0.0220 (7)
H11A	0.2383	0.0134	0.6003	0.026*
C12	0.2554 (4)	0.0409 (3)	0.4455 (2)	0.0168 (6)
C13	0.5092 (4)	0.2559 (3)	0.2620 (2)	0.0202 (7)
C14	0.1407 (4)	−0.0569 (3)	0.4255 (2)	0.0193 (7)
O9	0.7005 (3)	0.4732 (2)	0.46109 (18)	0.0300 (6)
N3	0.8635 (3)	0.5880 (3)	0.5417 (2)	0.0186 (6)
H3N	0.9098	0.6328	0.4886	0.028*
N4	0.7837 (3)	0.5199 (3)	0.7029 (2)	0.0202 (6)
N5	0.9931 (3)	0.6668 (3)	0.6669 (2)	0.0213 (6)
H5NB	0.9862	0.6905	0.7286	0.032*
H5NA	1.0388	0.7217	0.6217	0.032*
C15	0.7458 (4)	0.5019 (3)	0.5378 (3)	0.0217 (7)
C16	0.8858 (4)	0.5953 (3)	0.6403 (2)	0.0185 (6)
C17	0.6828 (4)	0.4533 (3)	0.6458 (3)	0.0226 (7)
H17A	0.5647	0.4771	0.6499	0.027*
H17B	0.6996	0.3585	0.6710	0.027*
C18	0.7939 (5)	0.4855 (4)	0.8144 (3)	0.0288 (8)
H18A	0.8137	0.5627	0.8376	0.043*
H18B	0.8844	0.4214	0.8376	0.043*
H18C	0.6904	0.4491	0.8429	0.043*
O1W	0.9969 (3)	0.7014 (2)	0.35667 (18)	0.0257 (5)
H1WA	0.9086	0.6978	0.3243	0.038*
H1WB	1.0206	0.7804	0.3398	0.038*
O2W	0.7807 (3)	0.4512 (2)	0.10606 (19)	0.0310 (6)
H2WA	0.7267	0.3996	0.1517	0.046*
H2WB	0.8208	0.4006	0.0723	0.046*
H2WC	0.7360	0.5102	0.0580	0.046*
O3W	0.7459 (3)	0.6405 (3)	0.2550 (2)	0.0385 (7)
H3WA	0.7188	0.5734	0.3000	0.058*
H3WB	0.6564	0.6811	0.2316	0.058*
O4W	0.6023 (4)	0.6403 (3)	0.0074 (2)	0.0454 (8)
H4WA	0.5592	0.6919	0.0393	0.068*
H4WB	0.5964	0.6694	−0.0574	0.068*

	U11	U22	U33	U12	U13	U23
Ni1	0.0227 (2)	0.0187 (2)	0.0156 (2)	−0.00178 (16)	−0.00045 (16)	−0.00419 (16)
O1	0.0295 (13)	0.0209 (12)	0.0176 (11)	0.0012 (10)	0.0011 (10)	−0.0064 (9)
O2	0.0315 (13)	0.0208 (12)	0.0220 (12)	0.0086 (10)	−0.0026 (10)	−0.0087 (10)
O3	0.0254 (12)	0.0215 (12)	0.0168 (11)	0.0008 (10)	0.0001 (9)	−0.0062 (9)
O4	0.0287 (13)	0.0262 (13)	0.0193 (12)	0.0074 (10)	−0.0034 (10)	−0.0040 (10)
O5	0.0249 (12)	0.0263 (12)	0.0155 (11)	−0.0045 (10)	0.0021 (9)	−0.0060 (9)
O6	0.0306 (14)	0.0279 (13)	0.0220 (12)	−0.0110 (11)	0.0015 (10)	−0.0038 (10)
O7	0.0294 (13)	0.0204 (12)	0.0186 (12)	−0.0068 (10)	0.0023 (10)	−0.0042 (9)
O8	0.0349 (14)	0.0231 (12)	0.0222 (12)	−0.0078 (11)	0.0060 (10)	−0.0027 (10)
N1	0.0151 (13)	0.0140 (12)	0.0186 (13)	−0.0019 (10)	0.0003 (10)	−0.0009 (10)
N2	0.0170 (13)	0.0132 (12)	0.0167 (13)	0.0031 (10)	0.0000 (10)	−0.0023 (10)
C1	0.0153 (15)	0.0184 (15)	0.0193 (16)	−0.0025 (12)	0.0014 (12)	−0.0058 (12)
C2	0.0194 (16)	0.0195 (16)	0.0226 (17)	−0.0040 (13)	0.0014 (13)	−0.0071 (13)
C3	0.0268 (18)	0.0234 (17)	0.0170 (16)	−0.0025 (14)	−0.0039 (13)	−0.0065 (13)
C4	0.0216 (17)	0.0204 (16)	0.0178 (16)	−0.0010 (13)	−0.0030 (13)	−0.0002 (12)
C5	0.0180 (16)	0.0158 (15)	0.0178 (15)	−0.0031 (12)	0.0026 (12)	−0.0031 (12)
C6	0.0182 (16)	0.0195 (16)	0.0187 (16)	−0.0032 (13)	0.0012 (12)	−0.0039 (13)
C7	0.0229 (17)	0.0175 (15)	0.0188 (16)	0.0005 (13)	−0.0011 (13)	−0.0019 (12)
C8	0.0146 (15)	0.0129 (14)	0.0233 (16)	0.0017 (12)	0.0007 (12)	−0.0021 (12)
C9	0.0204 (16)	0.0193 (16)	0.0216 (16)	0.0027 (13)	−0.0028 (13)	−0.0046 (13)
C10	0.0263 (18)	0.0221 (16)	0.0157 (15)	0.0054 (14)	−0.0040 (13)	−0.0066 (13)
C11	0.0242 (17)	0.0226 (17)	0.0164 (16)	0.0071 (14)	0.0006 (13)	−0.0012 (13)
C12	0.0148 (15)	0.0151 (15)	0.0193 (16)	0.0040 (12)	0.0008 (12)	−0.0032 (12)
C13	0.0204 (16)	0.0196 (16)	0.0195 (16)	0.0003 (13)	0.0004 (13)	−0.0030 (13)
C14	0.0180 (16)	0.0168 (15)	0.0232 (17)	0.0015 (12)	0.0016 (13)	−0.0055 (13)
O9	0.0341 (14)	0.0351 (14)	0.0227 (13)	−0.0115 (12)	−0.0032 (11)	−0.0094 (11)
N3	0.0211 (14)	0.0209 (14)	0.0132 (13)	−0.0024 (11)	0.0022 (10)	−0.0035 (10)
N4	0.0246 (15)	0.0185 (13)	0.0165 (13)	−0.0040 (11)	0.0016 (11)	−0.0021 (11)
N5	0.0267 (15)	0.0225 (14)	0.0140 (13)	−0.0018 (12)	−0.0001 (11)	−0.0034 (11)
C15	0.0211 (16)	0.0188 (16)	0.0241 (17)	−0.0007 (13)	−0.0012 (13)	−0.0037 (13)
C16	0.0199 (16)	0.0165 (15)	0.0179 (16)	0.0050 (12)	0.0009 (12)	−0.0032 (12)
C17	0.0220 (17)	0.0231 (17)	0.0220 (17)	−0.0050 (14)	−0.0002 (13)	−0.0043 (13)
C18	0.040 (2)	0.0268 (18)	0.0181 (17)	−0.0089 (16)	0.0017 (15)	−0.0015 (14)
O1W	0.0261 (13)	0.0248 (13)	0.0248 (13)	−0.0066 (10)	−0.0014 (10)	−0.0034 (10)
O2W	0.0373 (15)	0.0255 (13)	0.0266 (13)	0.0023 (11)	0.0072 (11)	−0.0013 (11)
O3W	0.0363 (16)	0.0365 (15)	0.0345 (15)	−0.0107 (12)	−0.0101 (12)	0.0067 (12)
O4W	0.082 (2)	0.0346 (15)	0.0169 (13)	0.0270 (15)	−0.0012 (13)	−0.0065 (11)

Ni1—N1	1.972 (3)	C10—C11	1.384 (5)
Ni1—N2	1.974 (3)	C10—H10A	0.9500
Ni1—O1	2.101 (2)	C11—C12	1.387 (4)
Ni1—O7	2.121 (2)	C11—H11A	0.9500
Ni1—O3	2.163 (2)	C12—C14	1.511 (4)
Ni1—O5	2.178 (2)	O9—C15	1.218 (4)
O1—C6	1.262 (4)	N3—C16	1.368 (4)
O2—C6	1.252 (4)	N3—C15	1.370 (4)
O3—C7	1.265 (4)	N3—H3N	0.8511
O4—C7	1.251 (4)	N4—C16	1.327 (4)
O5—C13	1.272 (4)	N4—C18	1.455 (4)
O6—C13	1.240 (4)	N4—C17	1.457 (4)
O7—C14	1.280 (4)	N5—C16	1.298 (4)
O8—C14	1.243 (4)	N5—H5NB	0.9334
N1—C1	1.330 (4)	N5—H5NA	0.8300
N1—C5	1.342 (4)	C15—C17	1.512 (5)
N2—C12	1.320 (4)	C17—H17A	0.9900
N2—C8	1.340 (4)	C17—H17B	0.9900
C1—C2	1.394 (4)	C18—H18A	0.9800
C1—C6	1.509 (4)	C18—H18B	0.9800
C2—C3	1.391 (5)	C18—H18C	0.9800
C2—H2A	0.9500	O1W—H1WA	0.8500
C3—C4	1.385 (5)	O1W—H1WB	0.8500
C3—H3A	0.9500	O2W—H2WA	0.8499
C4—C5	1.379 (4)	O2W—H2WB	0.8500
C4—H4A	0.9500	O2W—H2WC	0.8500
C5—C7	1.509 (4)	O3W—H3WA	0.8500
C8—C9	1.382 (5)	O3W—H3WB	0.8500
C8—C13	1.505 (4)	O4W—H4WA	0.8500
C9—C10	1.408 (5)	O4W—H4WB	0.8500
C9—H9A	0.9500
N1—Ni1—N2	174.74 (11)	C8—C9—H9A	120.8
N1—Ni1—O1	78.05 (10)	C10—C9—H9A	120.8
N2—Ni1—O1	101.80 (10)	C11—C10—C9	118.8 (3)
N1—Ni1—O7	106.74 (10)	C11—C10—H10A	120.6
N2—Ni1—O7	78.49 (10)	C9—C10—H10A	120.6
O1—Ni1—O7	89.16 (9)	C10—C11—C12	119.3 (3)
N1—Ni1—O3	77.19 (9)	C10—C11—H11A	120.3
N2—Ni1—O3	103.06 (9)	C12—C11—H11A	120.3
O1—Ni1—O3	155.14 (9)	N2—C12—C11	121.0 (3)
O7—Ni1—O3	95.81 (9)	N2—C12—C14	112.9 (3)
N1—Ni1—O5	98.03 (9)	C11—C12—C14	126.1 (3)
N2—Ni1—O5	76.74 (10)	O6—C13—O5	126.9 (3)
O1—Ni1—O5	96.01 (9)	O6—C13—C8	117.6 (3)
O7—Ni1—O5	155.22 (9)	O5—C13—C8	115.5 (3)
O3—Ni1—O5	89.63 (9)	O8—C14—O7	125.9 (3)
C6—O1—Ni1	114.6 (2)	O8—C14—C12	118.2 (3)
C7—O3—Ni1	113.8 (2)	O7—C14—C12	115.9 (3)
C13—O5—Ni1	114.4 (2)	C16—N3—C15	110.3 (3)
C14—O7—Ni1	112.9 (2)	C16—N3—H3N	126.5
C1—N1—C5	121.1 (3)	C15—N3—H3N	123.1
C1—N1—Ni1	118.9 (2)	C16—N4—C18	125.2 (3)
C5—N1—Ni1	119.8 (2)	C16—N4—C17	110.3 (3)
C12—N2—C8	121.4 (3)	C18—N4—C17	123.3 (3)
C12—N2—Ni1	118.5 (2)	C16—N5—H5NB	122.1
C8—N2—Ni1	120.1 (2)	C16—N5—H5NA	119.2
N1—C1—C2	120.9 (3)	H5NB—N5—H5NA	111.9
N1—C1—C6	111.8 (3)	O9—C15—N3	125.8 (3)
C2—C1—C6	127.3 (3)	O9—C15—C17	127.5 (3)
C3—C2—C1	118.1 (3)	N3—C15—C17	106.7 (3)
C3—C2—H2A	120.9	N5—C16—N4	125.9 (3)
C1—C2—H2A	120.9	N5—C16—N3	123.6 (3)
C4—C3—C2	120.3 (3)	N4—C16—N3	110.6 (3)
C4—C3—H3A	119.8	N4—C17—C15	102.1 (3)
C2—C3—H3A	119.8	N4—C17—H17A	111.3
C5—C4—C3	118.3 (3)	C15—C17—H17A	111.3
C5—C4—H4A	120.9	N4—C17—H17B	111.3
C3—C4—H4A	120.9	C15—C17—H17B	111.3
N1—C5—C4	121.3 (3)	H17A—C17—H17B	109.2
N1—C5—C7	112.1 (3)	N4—C18—H18A	109.5
C4—C5—C7	126.6 (3)	N4—C18—H18B	109.5
O2—C6—O1	125.8 (3)	H18A—C18—H18B	109.5
O2—C6—C1	118.1 (3)	N4—C18—H18C	109.5
O1—C6—C1	116.1 (3)	H18A—C18—H18C	109.5
O4—C7—O3	126.4 (3)	H18B—C18—H18C	109.5
O4—C7—C5	117.0 (3)	H1WA—O1W—H1WB	105.5
O3—C7—C5	116.6 (3)	H2WA—O2W—H2WB	101.4
N2—C8—C9	121.1 (3)	H2WA—O2W—H2WC	123.5
N2—C8—C13	113.2 (3)	H2WB—O2W—H2WC	100.7
C9—C8—C13	125.7 (3)	H3WA—O3W—H3WB	106.0
C8—C9—C10	118.4 (3)	H4WA—O4W—H4WB	113.1
N1—Ni1—O1—C6	−3.8 (2)	Ni1—O1—C6—O2	−172.4 (3)
N2—Ni1—O1—C6	−178.4 (2)	Ni1—O1—C6—C1	7.4 (3)
O7—Ni1—O1—C6	103.5 (2)	N1—C1—C6—O2	171.8 (3)
O3—Ni1—O1—C6	1.4 (4)	C2—C1—C6—O2	−8.7 (5)
O5—Ni1—O1—C6	−100.8 (2)	N1—C1—C6—O1	−8.1 (4)
N1—Ni1—O3—C7	−4.7 (2)	C2—C1—C6—O1	171.5 (3)
N2—Ni1—O3—C7	169.9 (2)	Ni1—O3—C7—O4	−179.7 (3)
O1—Ni1—O3—C7	−10.0 (4)	Ni1—O3—C7—C5	2.4 (3)
O7—Ni1—O3—C7	−110.6 (2)	N1—C5—C7—O4	−175.4 (3)
O5—Ni1—O3—C7	93.6 (2)	C4—C5—C7—O4	4.0 (5)
N1—Ni1—O5—C13	178.0 (2)	N1—C5—C7—O3	2.7 (4)
N2—Ni1—O5—C13	−2.5 (2)	C4—C5—C7—O3	−177.9 (3)
O1—Ni1—O5—C13	−103.3 (2)	C12—N2—C8—C9	−1.0 (4)
O7—Ni1—O5—C13	−2.2 (4)	Ni1—N2—C8—C9	−179.2 (2)
O3—Ni1—O5—C13	101.0 (2)	C12—N2—C8—C13	177.3 (3)
N1—Ni1—O7—C14	170.5 (2)	Ni1—N2—C8—C13	−1.0 (3)
N2—Ni1—O7—C14	−8.9 (2)	N2—C8—C9—C10	−0.6 (5)
O1—Ni1—O7—C14	93.3 (2)	C13—C8—C9—C10	−178.7 (3)
O3—Ni1—O7—C14	−111.1 (2)	C8—C9—C10—C11	1.4 (5)
O5—Ni1—O7—C14	−9.3 (4)	C9—C10—C11—C12	−0.7 (5)
O1—Ni1—N1—C1	−1.0 (2)	C8—N2—C12—C11	1.8 (4)
O7—Ni1—N1—C1	−86.4 (2)	Ni1—N2—C12—C11	−179.9 (2)
O3—Ni1—N1—C1	−178.7 (2)	C8—N2—C12—C14	−176.9 (3)
O5—Ni1—N1—C1	93.5 (2)	Ni1—N2—C12—C14	1.4 (3)
O1—Ni1—N1—C5	−175.6 (2)	C10—C11—C12—N2	−0.9 (5)
O7—Ni1—N1—C5	98.9 (2)	C10—C11—C12—C14	177.5 (3)
O3—Ni1—N1—C5	6.6 (2)	Ni1—O5—C13—O6	−176.5 (3)
O5—Ni1—N1—C5	−81.1 (2)	Ni1—O5—C13—C8	2.8 (3)
O1—Ni1—N2—C12	−83.0 (2)	N2—C8—C13—O6	178.0 (3)
O7—Ni1—N2—C12	3.6 (2)	C9—C8—C13—O6	−3.9 (5)
O3—Ni1—N2—C12	97.0 (2)	N2—C8—C13—O5	−1.3 (4)
O5—Ni1—N2—C12	−176.5 (2)	C9—C8—C13—O5	176.8 (3)
O1—Ni1—N2—C8	95.3 (2)	Ni1—O7—C14—O8	−165.9 (3)
O7—Ni1—N2—C8	−178.0 (2)	Ni1—O7—C14—C12	12.2 (3)
O3—Ni1—N2—C8	−84.7 (2)	N2—C12—C14—O8	168.8 (3)
O5—Ni1—N2—C8	1.8 (2)	C11—C12—C14—O8	−9.8 (5)
C5—N1—C1—C2	−0.3 (4)	N2—C12—C14—O7	−9.5 (4)
Ni1—N1—C1—C2	−174.8 (2)	C11—C12—C14—O7	171.9 (3)
C5—N1—C1—C6	179.3 (3)	C16—N3—C15—O9	−178.9 (3)
Ni1—N1—C1—C6	4.8 (3)	C16—N3—C15—C17	2.2 (4)
N1—C1—C2—C3	1.3 (5)	C18—N4—C16—N5	−11.9 (5)
C6—C1—C2—C3	−178.2 (3)	C17—N4—C16—N5	−179.3 (3)
C1—C2—C3—C4	−0.9 (5)	C18—N4—C16—N3	167.9 (3)
C2—C3—C4—C5	−0.5 (5)	C17—N4—C16—N3	0.5 (4)
C1—N1—C5—C4	−1.2 (5)	C15—N3—C16—N5	178.1 (3)
Ni1—N1—C5—C4	173.3 (2)	C15—N3—C16—N4	−1.8 (4)
C1—N1—C5—C7	178.2 (3)	C16—N4—C17—C15	0.8 (3)
Ni1—N1—C5—C7	−7.3 (3)	C18—N4—C17—C15	−166.9 (3)
C3—C4—C5—N1	1.6 (5)	O9—C15—C17—N4	179.4 (3)
C3—C4—C5—C7	−177.8 (3)	N3—C15—C17—N4	−1.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1W	0.85	1.89	2.726 (4)	166
N5—H5NB···O3i	0.93	1.96	2.861 (4)	162
N5—H5NA···O8ii	0.83	1.97	2.777 (4)	165
O1W—H1WA···O3W	0.85	1.84	2.662 (3)	162
O1W—H1WB···O7ii	0.85	1.97	2.804 (3)	166
O2W—H2WA···O6	0.85	1.71	2.529 (3)	161
O2W—H2WB···O4iii	0.85	1.65	2.480 (3)	165
O2W—H2WC···O4W	0.85	1.73	2.521 (3)	155
O3W—H3WA···O9	0.85	2.17	2.926 (4)	148
O3W—H3WB···O2iv	0.85	1.94	2.765 (4)	162
O4W—H4WA···O2iv	0.85	1.85	2.682 (4)	165
O4W—H4WB···O5v	0.85	1.91	2.722 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1W	0.85	1.89	2.726 (4)	166
N5—H5NB⋯O3i	0.93	1.96	2.861 (4)	162
N5—H5NA⋯O8ii	0.83	1.97	2.777 (4)	165
O1W—H1WA⋯O3W	0.85	1.84	2.662 (3)	162
O1W—H1WB⋯O7ii	0.85	1.97	2.804 (3)	166
O2W—H2WA⋯O6	0.85	1.71	2.529 (3)	161
O2W—H2WB⋯O4iii	0.85	1.65	2.480 (3)	165
O2W—H2WC⋯O4W	0.85	1.73	2.521 (3)	155
O3W—H3WA⋯O9	0.85	2.17	2.926 (4)	148
O3W—H3WB⋯O2iv	0.85	1.94	2.765 (4)	162
O4W—H4WA⋯O2iv	0.85	1.85	2.682 (4)	165
O4W—H4WB⋯O5v	0.85	1.91	2.722 (4)	159

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