(2-Amino-benzoato-κO,O')(rac-5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-decane-κN,N',N'',N''')nickel(II) perchlorate monohydrate.

In the title salt, [Ni(C(7)H(6)NO(2))(C(16)H(36)N(4))]ClO(4)·H(2)O, the Ni(II) cation is O,O'-chelated by the benzoate anion and N,N',N'',N'''-chelated by the macrocycle ligand, confering a distorted octa-hedral geometry on the metal atom. The complex cations, perchlorate anions and uncoordinated water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into a three-dimensional network. The perchlorate ion is disordered over two positions in a 0.554 (8):0.446 (8) ratio.

Related literature

For two related structures, see: Ou et al. (2008a ▶,b ▶).

Experimental

Crystal data

[Ni(C7H6NO2)(C16H36N4)]ClO4·H2O

M = 596.79

Monoclinic,

a = 9.6452 (5) Å

b = 21.5350 (11) Å

c = 13.5083 (7) Å

β = 90.784 (1)°

V = 2805.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.84 mm−1

T = 110 K

0.45 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.818, T max = 1.000

6638 measured reflections

3832 independent reflections

3667 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.064

S = 1.08

3832 reflections

410 parameters

142 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 874 Friedel pairs

Flack parameter: −0.012 (9)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037116/xu5028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037116/xu5028Isup2.hkl

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

[Ni(C7H6NO2)(C16H36N4)]ClO4·H2O	F(000) = 1272
Mr = 596.79	Dx = 1.413 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5267 reflections
a = 9.6452 (5) Å	θ = 2.3–27.0°
b = 21.5350 (11) Å	µ = 0.84 mm−1
c = 13.5083 (7) Å	T = 110 K
β = 90.784 (1)°	Prism, violet
V = 2805.5 (3) Å3	0.45 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	3832 independent reflections
Radiation source: fine-focus sealed tube	3667 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.818, Tmax = 1.000	k = −26→26
6638 measured reflections	l = −8→17

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.1275P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3832 reflections	Δρmax = 0.25 e Å−3
410 parameters	Δρmin = −0.21 e Å−3
142 restraints	Absolute structure: Flack (1983), 874 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.012 (9)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.50011 (3)	0.399116 (12)	0.49992 (3)	0.01859 (8)
O1	0.58175 (16)	0.44546 (8)	0.37089 (12)	0.0219 (4)
O2	0.66792 (16)	0.46225 (7)	0.51979 (12)	0.0201 (3)
Cl1	0.6956 (5)	0.2675 (2)	0.1539 (3)	0.0295 (7)	0.554 (8)
O3	0.5575 (5)	0.2886 (4)	0.1347 (6)	0.0444 (19)	0.554 (8)
O4	0.7620 (5)	0.3111 (2)	0.2197 (4)	0.0581 (17)	0.554 (8)
O5	0.6945 (9)	0.2080 (2)	0.2001 (5)	0.0439 (19)	0.554 (8)
O6	0.7708 (7)	0.2650 (3)	0.0641 (4)	0.070 (2)	0.554 (8)
Cl1'	0.6956 (6)	0.2641 (3)	0.1262 (4)	0.0311 (10)	0.446 (8)
O3'	0.5794 (8)	0.2974 (4)	0.1623 (6)	0.042 (2)	0.446 (8)
O4'	0.8213 (6)	0.2957 (3)	0.1496 (6)	0.060 (3)	0.446 (8)
O5'	0.6992 (12)	0.2028 (3)	0.1656 (9)	0.057 (3)	0.446 (8)
O6'	0.6838 (8)	0.2577 (3)	0.0218 (4)	0.058 (2)	0.446 (8)
O1W	0.5173 (2)	0.42855 (9)	0.17034 (14)	0.0296 (4)
H11	0.545 (3)	0.4343 (13)	0.2291 (11)	0.044*
H12	0.537 (4)	0.3925 (8)	0.153 (2)	0.044*
N1	0.3714 (2)	0.46844 (10)	0.56243 (16)	0.0190 (4)
H1	0.423 (2)	0.4982 (10)	0.585 (2)	0.023*
N2	0.4909 (2)	0.35763 (9)	0.63905 (16)	0.0211 (4)
H2	0.428 (2)	0.3296 (10)	0.636 (2)	0.025*
N3	0.6127 (2)	0.32080 (10)	0.44631 (17)	0.0243 (4)
H3	0.652 (3)	0.3351 (13)	0.3944 (14)	0.029*
N4	0.3296 (2)	0.36063 (10)	0.42555 (16)	0.0242 (4)
H4	0.280 (3)	0.3380 (12)	0.4632 (19)	0.029*
N5	0.7978 (2)	0.57537 (11)	0.53966 (18)	0.0289 (5)
H51	0.739 (3)	0.5514 (12)	0.567 (2)	0.035*
H52	0.814 (3)	0.6115 (8)	0.563 (2)	0.035*
C1	0.3207 (3)	0.44029 (12)	0.65532 (18)	0.0245 (5)
H1A	0.2438	0.4112	0.6402	0.029*
H1B	0.2852	0.4732	0.6995	0.029*
C2	0.4374 (3)	0.40601 (11)	0.70620 (19)	0.0253 (5)
H2A	0.5126	0.4354	0.7241	0.030*
H2B	0.4037	0.3866	0.7678	0.030*
C3	0.6234 (3)	0.33020 (13)	0.6779 (2)	0.0282 (6)
H3a	0.6968	0.3629	0.6751	0.034*
C4	0.6109 (3)	0.30893 (15)	0.7856 (2)	0.0378 (7)
H4A	0.5814	0.3440	0.8265	0.057*
H4B	0.7011	0.2937	0.8096	0.057*
H4C	0.5423	0.2755	0.7895	0.057*
C5	0.6684 (3)	0.27612 (12)	0.6133 (2)	0.0293 (6)
H5A	0.5883	0.2477	0.6059	0.035*
H5B	0.7418	0.2532	0.6499	0.035*
C6	0.7230 (3)	0.28992 (12)	0.5088 (2)	0.0298 (6)
C7	0.8464 (3)	0.33447 (13)	0.5146 (2)	0.0353 (7)
H7A	0.8832	0.3409	0.4481	0.053*
H7B	0.9188	0.3167	0.5575	0.053*
H7C	0.8162	0.3743	0.5418	0.053*
C8	0.7727 (3)	0.22831 (14)	0.4626 (3)	0.0393 (7)
H8A	0.7921	0.2348	0.3923	0.059*
H8B	0.7003	0.1967	0.4692	0.059*
H8C	0.8573	0.2143	0.4969	0.059*
C9	0.5037 (3)	0.27846 (12)	0.4086 (2)	0.0297 (6)
H9A	0.4632	0.2551	0.4643	0.036*
H9B	0.5444	0.2483	0.3620	0.036*
C10	0.3920 (3)	0.31573 (13)	0.3564 (2)	0.0288 (6)
H10A	0.4324	0.3383	0.2998	0.035*
H10B	0.3194	0.2874	0.3304	0.035*
C11	0.2384 (3)	0.40671 (11)	0.37461 (19)	0.0241 (5)
H11A	0.2979	0.4328	0.3310	0.029*
C12	0.1271 (3)	0.37581 (15)	0.3090 (2)	0.0335 (6)
H12A	0.1719	0.3517	0.2568	0.050*
H12B	0.0680	0.4078	0.2788	0.050*
H12C	0.0704	0.3481	0.3494	0.050*
C13	0.1684 (2)	0.45014 (12)	0.44934 (19)	0.0238 (5)
H13A	0.1253	0.4240	0.5007	0.029*
H13B	0.0923	0.4722	0.4142	0.029*
C14	0.2594 (2)	0.49930 (12)	0.50235 (18)	0.0217 (5)
C15	0.3297 (3)	0.54169 (12)	0.42814 (19)	0.0237 (5)
H15A	0.3819	0.5740	0.4637	0.036*
H15B	0.2592	0.5611	0.3853	0.036*
H15C	0.3932	0.5173	0.3876	0.036*
C16	0.1671 (3)	0.54025 (13)	0.5675 (2)	0.0259 (6)
H16A	0.2256	0.5678	0.6079	0.039*
H16B	0.1117	0.5138	0.6109	0.039*
H16C	0.1053	0.5652	0.5253	0.039*
C17	0.6690 (2)	0.47306 (11)	0.42754 (19)	0.0186 (5)
C18	0.7701 (2)	0.51743 (11)	0.38477 (18)	0.0198 (5)
C19	0.8068 (2)	0.51078 (12)	0.28554 (19)	0.0234 (5)
H19	0.7678	0.4777	0.2479	0.028*
C20	0.8984 (3)	0.55104 (13)	0.2407 (2)	0.0292 (6)
H20	0.9247	0.5450	0.1739	0.035*
C21	0.9514 (3)	0.60087 (12)	0.2959 (2)	0.0301 (6)
H21	1.0125	0.6296	0.2657	0.036*
C22	0.9161 (3)	0.60871 (12)	0.3934 (2)	0.0276 (6)
H22	0.9532	0.6430	0.4292	0.033*
C23	0.8259 (2)	0.56699 (12)	0.4417 (2)	0.0219 (5)

	U11	U22	U33	U12	U13	U23
Ni1	0.01972 (13)	0.01555 (14)	0.02064 (13)	−0.00292 (12)	0.00605 (9)	−0.00109 (13)
O1	0.0225 (8)	0.0217 (9)	0.0217 (8)	−0.0068 (7)	0.0050 (7)	−0.0017 (7)
O2	0.0227 (8)	0.0171 (9)	0.0207 (8)	−0.0015 (6)	0.0043 (7)	−0.0002 (7)
Cl1	0.0273 (9)	0.0245 (10)	0.0371 (17)	0.0031 (6)	0.0107 (11)	0.0046 (11)
O3	0.036 (2)	0.035 (3)	0.062 (4)	0.005 (2)	−0.007 (2)	−0.016 (3)
O4	0.053 (3)	0.045 (3)	0.075 (4)	−0.004 (2)	−0.017 (3)	−0.008 (2)
O5	0.055 (3)	0.015 (2)	0.062 (4)	0.000 (2)	0.014 (3)	0.010 (2)
O6	0.071 (4)	0.077 (4)	0.065 (4)	0.031 (3)	0.052 (4)	0.012 (3)
Cl1'	0.0308 (12)	0.0213 (12)	0.041 (3)	0.0025 (8)	0.0045 (16)	0.0042 (15)
O3'	0.048 (4)	0.033 (4)	0.047 (4)	0.016 (3)	0.024 (3)	0.001 (3)
O4'	0.055 (3)	0.038 (3)	0.087 (6)	−0.014 (3)	−0.021 (3)	0.020 (3)
O5'	0.051 (4)	0.027 (4)	0.094 (7)	0.008 (3)	0.017 (5)	0.010 (4)
O6'	0.055 (4)	0.079 (4)	0.041 (3)	0.016 (3)	0.009 (3)	−0.017 (3)
O1W	0.0405 (11)	0.0243 (10)	0.0239 (9)	0.0039 (8)	−0.0026 (8)	0.0000 (7)
N1	0.0222 (10)	0.0145 (10)	0.0205 (10)	−0.0003 (8)	0.0027 (8)	0.0008 (8)
N2	0.0208 (10)	0.0180 (10)	0.0248 (10)	0.0008 (8)	0.0057 (8)	0.0009 (8)
N3	0.0254 (10)	0.0186 (11)	0.0291 (11)	−0.0042 (8)	0.0107 (9)	−0.0014 (9)
N4	0.0258 (10)	0.0228 (11)	0.0242 (10)	−0.0061 (8)	0.0086 (8)	−0.0022 (9)
N5	0.0337 (12)	0.0215 (11)	0.0315 (12)	−0.0095 (9)	0.0063 (9)	−0.0075 (9)
C1	0.0287 (12)	0.0262 (13)	0.0187 (11)	0.0058 (10)	0.0078 (10)	0.0013 (10)
C2	0.0314 (13)	0.0246 (13)	0.0202 (11)	0.0062 (10)	0.0056 (10)	0.0018 (10)
C3	0.0250 (12)	0.0240 (14)	0.0356 (15)	0.0034 (10)	0.0030 (11)	0.0032 (11)
C4	0.0416 (16)	0.0366 (16)	0.0353 (15)	0.0169 (13)	0.0014 (13)	0.0070 (13)
C5	0.0295 (13)	0.0180 (12)	0.0406 (15)	0.0043 (10)	0.0081 (11)	0.0038 (11)
C6	0.0245 (13)	0.0232 (14)	0.0420 (16)	0.0016 (10)	0.0122 (11)	−0.0024 (12)
C7	0.0229 (13)	0.0326 (16)	0.0507 (17)	0.0009 (11)	0.0090 (12)	−0.0002 (13)
C8	0.0370 (16)	0.0235 (15)	0.058 (2)	0.0074 (12)	0.0127 (15)	−0.0063 (14)
C9	0.0347 (13)	0.0181 (13)	0.0368 (14)	−0.0057 (10)	0.0146 (11)	−0.0073 (11)
C10	0.0315 (14)	0.0250 (14)	0.0301 (14)	−0.0081 (10)	0.0079 (11)	−0.0125 (11)
C11	0.0247 (12)	0.0247 (13)	0.0232 (12)	−0.0063 (9)	0.0049 (10)	−0.0010 (10)
C12	0.0295 (13)	0.0429 (17)	0.0282 (13)	−0.0081 (12)	0.0010 (11)	−0.0065 (12)
C13	0.0193 (11)	0.0276 (13)	0.0245 (12)	−0.0013 (9)	0.0031 (10)	0.0017 (10)
C14	0.0229 (11)	0.0224 (12)	0.0200 (11)	0.0015 (9)	0.0040 (9)	0.0031 (10)
C15	0.0278 (12)	0.0222 (12)	0.0212 (11)	0.0021 (9)	0.0048 (10)	0.0034 (10)
C16	0.0263 (13)	0.0259 (15)	0.0256 (13)	0.0059 (10)	0.0062 (10)	0.0040 (11)
C17	0.0197 (11)	0.0140 (11)	0.0222 (12)	0.0024 (9)	0.0045 (9)	−0.0008 (9)
C18	0.0190 (11)	0.0170 (12)	0.0236 (12)	0.0000 (8)	0.0017 (9)	0.0014 (9)
C19	0.0210 (12)	0.0238 (13)	0.0255 (12)	−0.0011 (9)	0.0037 (10)	0.0014 (10)
C20	0.0253 (12)	0.0355 (15)	0.0269 (13)	0.0006 (10)	0.0083 (10)	0.0080 (11)
C21	0.0210 (12)	0.0288 (14)	0.0405 (15)	−0.0034 (9)	0.0045 (11)	0.0131 (12)
C22	0.0249 (12)	0.0199 (13)	0.0378 (15)	−0.0048 (9)	−0.0005 (11)	0.0034 (11)
C23	0.0194 (11)	0.0193 (12)	0.0269 (12)	0.0015 (9)	0.0022 (10)	0.0017 (10)

Ni1—N1	2.124 (2)	C5—C6	1.541 (4)
Ni1—N2	2.084 (2)	C5—H5A	0.9900
Ni1—N3	2.138 (2)	C5—H5B	0.9900
Ni1—N4	2.087 (2)	C6—C7	1.530 (4)
Ni1—O1	2.1659 (17)	C6—C8	1.546 (4)
Ni1—O2	2.1280 (16)	C7—H7A	0.9800
O1—C17	1.276 (3)	C7—H7B	0.9800
O2—C17	1.268 (3)	C7—H7C	0.9800
Cl1—O6	1.423 (4)	C8—H8A	0.9800
Cl1—O5	1.425 (5)	C8—H8B	0.9800
Cl1—O3	1.427 (5)	C8—H8C	0.9800
Cl1—O4	1.437 (5)	C9—C10	1.510 (4)
Cl1'—O6'	1.421 (5)	C9—H9A	0.9900
Cl1'—O5'	1.423 (6)	C9—H9B	0.9900
Cl1'—O3'	1.422 (5)	C10—H10A	0.9900
Cl1'—O4'	1.422 (6)	C10—H10B	0.9900
O1W—H11	0.843 (10)	C11—C12	1.534 (4)
O1W—H12	0.833 (10)	C11—C13	1.539 (3)
N1—C1	1.482 (3)	C11—H11A	1.0000
N1—C14	1.498 (3)	C12—H12A	0.9800
N1—H1	0.861 (10)	C12—H12B	0.9800
N2—C2	1.479 (3)	C12—H12C	0.9800
N2—C3	1.496 (3)	C13—C14	1.545 (3)
N2—H2	0.858 (10)	C13—H13A	0.9900
N3—C9	1.477 (3)	C13—H13B	0.9900
N3—C6	1.504 (4)	C14—C15	1.522 (3)
N3—H3	0.860 (10)	C14—C16	1.538 (3)
N4—C10	1.478 (3)	C15—H15A	0.9800
N4—C11	1.489 (3)	C15—H15B	0.9800
N4—H4	0.86 (3)	C15—H15C	0.9800
N5—C23	1.366 (3)	C16—H16A	0.9800
N5—H51	0.86 (3)	C16—H16B	0.9800
N5—H52	0.854 (10)	C16—H16C	0.9800
C1—C2	1.504 (3)	C17—C18	1.487 (3)
C1—H1A	0.9900	C18—C19	1.399 (3)
C1—H1B	0.9900	C18—C23	1.418 (3)
C2—H2A	0.9900	C19—C20	1.383 (3)
C2—H2B	0.9900	C19—H19	0.9500
C3—C5	1.522 (4)	C20—C21	1.400 (4)
C3—C4	1.532 (4)	C20—H20	0.9500
C3—H3a	1.0000	C21—C22	1.375 (4)
C4—H4A	0.9800	C21—H21	0.9500
C4—H4B	0.9800	C22—C23	1.416 (4)
C4—H4C	0.9800	C22—H22	0.9500
N2—Ni1—N4	102.76 (8)	N3—C6—C7	107.2 (2)
N2—Ni1—N1	84.86 (8)	N3—C6—C5	110.60 (19)
N4—Ni1—N1	90.54 (8)	C7—C6—C5	110.5 (2)
N2—Ni1—O2	101.64 (7)	N3—C6—C8	111.9 (2)
N4—Ni1—O2	155.16 (8)	C7—C6—C8	108.2 (2)
N1—Ni1—O2	87.05 (7)	C5—C6—C8	108.4 (2)
N2—Ni1—N3	89.73 (8)	C6—C7—H7A	109.5
N4—Ni1—N3	85.66 (8)	C6—C7—H7B	109.5
N1—Ni1—N3	172.56 (8)	H7A—C7—H7B	109.5
O2—Ni1—N3	99.07 (7)	C6—C7—H7C	109.5
N2—Ni1—O1	160.67 (7)	H7A—C7—H7C	109.5
N4—Ni1—O1	95.07 (7)	H7B—C7—H7C	109.5
N1—Ni1—O1	102.53 (7)	C6—C8—H8A	109.5
O2—Ni1—O1	61.50 (6)	C6—C8—H8B	109.5
N3—Ni1—O1	84.20 (7)	H8A—C8—H8B	109.5
C17—O1—Ni1	88.63 (14)	C6—C8—H8C	109.5
C17—O2—Ni1	90.56 (14)	H8A—C8—H8C	109.5
O6—Cl1—O5	110.2 (4)	H8B—C8—H8C	109.5
O6—Cl1—O3	110.1 (4)	N3—C9—C10	109.4 (2)
O5—Cl1—O3	110.7 (4)	N3—C9—H9A	109.8
O6—Cl1—O4	108.9 (4)	C10—C9—H9A	109.8
O5—Cl1—O4	108.8 (4)	N3—C9—H9B	109.8
O3—Cl1—O4	108.1 (4)	C10—C9—H9B	109.8
O6'—Cl1'—O5'	106.4 (7)	H9A—C9—H9B	108.2
O6'—Cl1'—O3'	109.6 (5)	N4—C10—C9	110.3 (2)
O5'—Cl1'—O3'	110.8 (5)	N4—C10—H10A	109.6
O6'—Cl1'—O4'	108.9 (5)	C9—C10—H10A	109.6
O5'—Cl1'—O4'	110.2 (5)	N4—C10—H10B	109.6
O3'—Cl1'—O4'	110.8 (5)	C9—C10—H10B	109.6
H11—O1W—H12	109.4 (17)	H10A—C10—H10B	108.1
C1—N1—C14	113.35 (19)	N4—C11—C12	112.5 (2)
C1—N1—Ni1	104.50 (15)	N4—C11—C13	111.3 (2)
C14—N1—Ni1	121.17 (16)	C12—C11—C13	109.5 (2)
C1—N1—H1	101.7 (19)	N4—C11—H11A	107.8
C14—N1—H1	105.3 (19)	C12—C11—H11A	107.8
Ni1—N1—H1	109.1 (18)	C13—C11—H11A	107.8
C2—N2—C3	111.5 (2)	C11—C12—H12A	109.5
C2—N2—Ni1	105.70 (15)	C11—C12—H12B	109.5
C3—N2—Ni1	116.01 (15)	H12A—C12—H12B	109.5
C2—N2—H2	106 (2)	C11—C12—H12C	109.5
C3—N2—H2	110 (2)	H12A—C12—H12C	109.5
Ni1—N2—H2	107 (2)	H12B—C12—H12C	109.5
C9—N3—C6	114.5 (2)	C11—C13—C14	117.97 (19)
C9—N3—Ni1	103.96 (15)	C11—C13—H13A	107.8
C6—N3—Ni1	121.14 (16)	C14—C13—H13A	107.8
C9—N3—H3	105 (2)	C11—C13—H13B	107.8
C6—N3—H3	107 (2)	C14—C13—H13B	107.8
Ni1—N3—H3	103 (2)	H13A—C13—H13B	107.2
C10—N4—C11	112.8 (2)	N1—C14—C15	107.37 (19)
C10—N4—Ni1	103.81 (15)	N1—C14—C16	111.3 (2)
C11—N4—Ni1	114.50 (15)	C15—C14—C16	107.4 (2)
C10—N4—H4	104 (2)	N1—C14—C13	110.4 (2)
C11—N4—H4	109 (2)	C15—C14—C13	111.2 (2)
Ni1—N4—H4	113 (2)	C16—C14—C13	109.19 (19)
C23—N5—H51	119 (2)	C14—C15—H15A	109.5
C23—N5—H52	116 (2)	C14—C15—H15B	109.5
H51—N5—H52	121 (3)	H15A—C15—H15B	109.5
N1—C1—C2	109.5 (2)	C14—C15—H15C	109.5
N1—C1—H1A	109.8	H15A—C15—H15C	109.5
C2—C1—H1A	109.8	H15B—C15—H15C	109.5
N1—C1—H1B	109.8	C14—C16—H16A	109.5
C2—C1—H1B	109.8	C14—C16—H16B	109.5
H1A—C1—H1B	108.2	H16A—C16—H16B	109.5
N2—C2—C1	109.3 (2)	C14—C16—H16C	109.5
N2—C2—H2A	109.8	H16A—C16—H16C	109.5
C1—C2—H2A	109.8	H16B—C16—H16C	109.5
N2—C2—H2B	109.8	O2—C17—O1	119.3 (2)
C1—C2—H2B	109.8	O2—C17—C18	120.9 (2)
H2A—C2—H2B	108.3	O1—C17—C18	119.8 (2)
N2—C3—C5	110.5 (2)	C19—C18—C23	119.9 (2)
N2—C3—C4	111.9 (2)	C19—C18—C17	118.9 (2)
C5—C3—C4	110.0 (2)	C23—C18—C17	121.3 (2)
N2—C3—H3a	108.1	C20—C19—C18	121.8 (2)
C5—C3—H3a	108.1	C20—C19—H19	119.1
C4—C3—H3a	108.1	C18—C19—H19	119.1
C3—C4—H4A	109.5	C19—C20—C21	118.6 (2)
C3—C4—H4B	109.5	C19—C20—H20	120.7
H4A—C4—H4B	109.5	C21—C20—H20	120.7
C3—C4—H4C	109.5	C22—C21—C20	120.7 (2)
H4A—C4—H4C	109.5	C22—C21—H21	119.6
H4B—C4—H4C	109.5	C20—C21—H21	119.6
C3—C5—C6	118.7 (2)	C21—C22—C23	121.7 (3)
C3—C5—H5A	107.6	C21—C22—H22	119.1
C6—C5—H5A	107.6	C23—C22—H22	119.1
C3—C5—H5B	107.6	N5—C23—C18	123.1 (2)
C6—C5—H5B	107.6	N5—C23—C22	119.6 (2)
H5A—C5—H5B	107.1	C18—C23—C22	117.3 (2)
N2—Ni1—O1—C17	−31.3 (3)	C2—N2—C3—C4	51.2 (3)
N4—Ni1—O1—C17	171.28 (14)	Ni1—N2—C3—C4	172.23 (19)
N1—Ni1—O1—C17	79.59 (14)	N2—C3—C5—C6	71.2 (3)
O2—Ni1—O1—C17	0.00 (13)	C4—C3—C5—C6	−164.7 (2)
N3—Ni1—O1—C17	−103.62 (14)	C9—N3—C6—C7	163.1 (2)
N2—Ni1—O2—C17	169.89 (14)	Ni1—N3—C6—C7	−71.0 (2)
N4—Ni1—O2—C17	−21.1 (2)	C9—N3—C6—C5	−76.4 (3)
N1—Ni1—O2—C17	−105.97 (14)	Ni1—N3—C6—C5	49.4 (3)
N3—Ni1—O2—C17	78.28 (15)	C9—N3—C6—C8	44.6 (3)
O1—Ni1—O2—C17	0.00 (13)	Ni1—N3—C6—C8	170.46 (18)
N2—Ni1—N1—C1	−14.19 (16)	C3—C5—C6—N3	−61.6 (3)
N4—Ni1—N1—C1	88.57 (16)	C3—C5—C6—C7	56.8 (3)
O2—Ni1—N1—C1	−116.17 (16)	C3—C5—C6—C8	175.3 (2)
O1—Ni1—N1—C1	−176.11 (15)	C6—N3—C9—C10	174.1 (2)
N2—Ni1—N1—C14	−143.61 (18)	Ni1—N3—C9—C10	39.7 (2)
N4—Ni1—N1—C14	−40.84 (18)	C11—N4—C10—C9	169.1 (2)
O2—Ni1—N1—C14	114.42 (17)	Ni1—N4—C10—C9	44.6 (2)
O1—Ni1—N1—C14	54.48 (18)	N3—C9—C10—N4	−59.9 (3)
N4—Ni1—N2—C2	−104.54 (16)	C10—N4—C11—C12	53.3 (3)
N1—Ni1—N2—C2	−15.15 (16)	Ni1—N4—C11—C12	171.73 (16)
O2—Ni1—N2—C2	70.77 (16)	C10—N4—C11—C13	176.57 (19)
N3—Ni1—N2—C2	169.98 (16)	Ni1—N4—C11—C13	−65.0 (2)
O1—Ni1—N2—C2	98.6 (2)	N4—C11—C13—C14	71.8 (3)
N4—Ni1—N2—C3	131.31 (17)	C12—C11—C13—C14	−163.2 (2)
N1—Ni1—N2—C3	−139.30 (18)	C1—N1—C14—C15	163.3 (2)
O2—Ni1—N2—C3	−53.38 (18)	Ni1—N1—C14—C15	−71.2 (2)
N3—Ni1—N2—C3	45.83 (18)	C1—N1—C14—C16	46.1 (3)
O1—Ni1—N2—C3	−25.6 (3)	Ni1—N1—C14—C16	171.49 (16)
N2—Ni1—N3—C9	90.51 (16)	C1—N1—C14—C13	−75.4 (2)
N4—Ni1—N3—C9	−12.31 (16)	Ni1—N1—C14—C13	50.1 (2)
O2—Ni1—N3—C9	−167.74 (16)	C11—C13—C14—N1	−61.3 (3)
O1—Ni1—N3—C9	−107.87 (16)	C11—C13—C14—C15	57.7 (3)
N2—Ni1—N3—C6	−40.04 (18)	C11—C13—C14—C16	176.0 (2)
N4—Ni1—N3—C6	−142.86 (18)	Ni1—O2—C17—O1	0.0 (2)
O2—Ni1—N3—C6	61.70 (18)	Ni1—O2—C17—C18	179.87 (19)
O1—Ni1—N3—C6	121.58 (18)	Ni1—O1—C17—O2	0.0 (2)
N2—Ni1—N4—C10	−105.88 (17)	Ni1—O1—C17—C18	−179.88 (19)
N1—Ni1—N4—C10	169.26 (17)	O2—C17—C18—C19	155.0 (2)
O2—Ni1—N4—C10	85.1 (2)	O1—C17—C18—C19	−25.2 (3)
N3—Ni1—N4—C10	−17.14 (17)	O2—C17—C18—C23	−26.9 (3)
O1—Ni1—N4—C10	66.63 (17)	O1—C17—C18—C23	152.9 (2)
N2—Ni1—N4—C11	130.71 (15)	C23—C18—C19—C20	0.8 (4)
N1—Ni1—N4—C11	45.86 (16)	C17—C18—C19—C20	178.9 (2)
O2—Ni1—N4—C11	−38.3 (3)	C18—C19—C20—C21	−2.2 (4)
N3—Ni1—N4—C11	−140.55 (16)	C19—C20—C21—C22	1.7 (4)
O1—Ni1—N4—C11	−56.77 (16)	C20—C21—C22—C23	0.3 (4)
C14—N1—C1—C2	175.3 (2)	C19—C18—C23—N5	−178.1 (2)
Ni1—N1—C1—C2	41.4 (2)	C17—C18—C23—N5	3.8 (4)
C3—N2—C2—C1	169.3 (2)	C19—C18—C23—C22	1.1 (3)
Ni1—N2—C2—C1	42.4 (2)	C17—C18—C23—C22	−176.9 (2)
N1—C1—C2—N2	−58.6 (3)	C21—C22—C23—N5	177.6 (2)
C2—N2—C3—C5	174.1 (2)	C21—C22—C23—C18	−1.7 (4)
Ni1—N2—C3—C5	−64.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1wi	0.86 (2)	2.15 (2)	2.995 (3)	166 (2)
N2—H2···O5ii	0.86 (2)	2.56 (2)	3.304 (8)	147 (2)
N2—H2···O5'ii	0.86 (2)	2.35 (2)	3.125 (11)	150 (3)
N3—H3···O1	0.86 (2)	2.49 (3)	2.885 (3)	109 (2)
N4—H4···O6ii	0.86 (3)	2.61 (2)	3.343 (6)	145 (3)
N4—H4···O6'ii	0.86 (3)	2.40 (2)	3.195 (6)	155 (3)
N5—H51···O2	0.85 (3)	2.13 (3)	2.751 (3)	129 (2)
N5—H52···O4'i	0.85 (1)	2.32 (1)	3.155 (6)	168 (3)
O1w—H11···O1	0.84 (2)	1.96 (2)	2.795 (2)	172 (3)
O1w—H12···O3	0.83 (2)	2.26 (2)	3.077 (9)	167 (3)
O1w—H12···O3'	0.83 (2)	2.09 (2)	2.890 (9)	160 (3)

Table 1

Selected bond lengths (Å)

Ni1—N1	2.124 (2)
Ni1—N2	2.084 (2)
Ni1—N3	2.138 (2)
Ni1—N4	2.087 (2)
Ni1—O1	2.1659 (17)
Ni1—O2	2.1280 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1wi	0.86 (2)	2.15 (2)	2.995 (3)	166 (2)
N2—H2⋯O5′ii	0.86 (2)	2.35 (2)	3.125 (11)	150 (3)
N3—H3⋯O1	0.86 (2)	2.49 (3)	2.885 (3)	109 (2)
N4—H4⋯O6′ii	0.86 (3)	2.40 (2)	3.195 (6)	155 (3)
N5—H51⋯O2	0.85 (3)	2.13 (3)	2.751 (3)	129 (2)
N5—H52⋯O4′i	0.85 (1)	2.32 (1)	3.155 (6)	168 (3)
O1w—H11⋯O1	0.84 (2)	1.96 (2)	2.795 (2)	172 (3)
O1w—H12⋯O3	0.83 (2)	2.26 (2)	3.077 (9)	167 (3)
O1w—H12⋯O3′	0.83 (2)	2.09 (2)	2.890 (9)	160 (3)

Symmetry codes: (i) ; (ii) .