(Benzoato-κO,O')(5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-azacyclo-tetra-decane-κN,N',N'',N''')nickel(II) perchlorate benzoic acid solvate.

In the title compound, [Ni(C(7)H(5)O(2))(C(16)H(36)N(4))]ClO(4)·C(7)H(6)O(2), the Ni atom displays a distorted octa-hedral coordination geometry with four N atoms of the ligand rac-5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-azacyclo-tetra-decane (L) in a folded configuration and two benzoate (bz) O atoms. The [Ni(rac-L)(bz)](+) complex cation, perchlorate anion and benzoic acid mol-ecules engage in hydrogen bonding, with N⋯O distances between 2.970 (3) and 3.123 (3) Å and an O⋯O distance of 2.691 (3) Å.

Related literature

For related background, see: Tait & Busch (1976 ▶); Curtis (1965 ▶). For related structures, see: Ou et al. (2008 ▶); Basiuk et al. (2001 ▶); Jiang et al. (2005 ▶).

Experimental

Crystal data

[Ni(C7H5O2)(C16H36N4)]ClO4·C7H6O2

M = 685.88

Monoclinic,

a = 8.8035 (11) Å

b = 18.138 (2) Å

c = 20.966 (3) Å

β = 95.512 (2)°

V = 3332.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.72 mm−1

T = 293 (2) K

0.48 × 0.26 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.725, T max = 0.900

22312 measured reflections

7304 independent reflections

5272 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.11

7304 reflections

404 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 1997 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038051/pv2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038051/pv2117Isup2.hkl

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

[Ni(C7H5O2)(C16H36N4)]ClO4·C7H6O2	F000 = 1456
Mr = 685.88	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 8.8035 (11) Å	Cell parameters from 7647 reflections
b = 18.138 (2) Å	θ = 2.3–26.9º
c = 20.966 (3) Å	µ = 0.72 mm−1
β = 95.512 (2)º	T = 293 (2) K
V = 3332.4 (7) Å3	Prism, light-blue
Z = 4	0.48 × 0.26 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	7304 independent reflections
Radiation source: fine-focus sealed tube	5272 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 293(2) K	θmax = 27.1º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.725, Tmax = 0.900	k = −20→23
22312 measured reflections	l = −26→26

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.7856P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
7304 reflections	Δρmax = 0.58 e Å−3
404 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.64844 (4)	0.771339 (17)	0.564296 (14)	0.01920 (11)
Cl1	0.08075 (7)	0.70176 (4)	0.44238 (3)	0.02611 (16)
N3	0.5075 (2)	0.77519 (11)	0.47565 (9)	0.0208 (5)
H3C	0.4098	0.7716	0.4861	0.025*
N1	0.8063 (2)	0.76085 (12)	0.64759 (9)	0.0219 (5)
H1C	0.7838	0.7983	0.6740	0.026*
O1	0.5623 (2)	0.87209 (10)	0.60812 (8)	0.0226 (4)
O2	0.4528 (2)	0.76422 (10)	0.61520 (8)	0.0253 (4)
N4	0.6736 (2)	0.65959 (12)	0.54328 (10)	0.0220 (5)
H4D	0.7638	0.6540	0.5260	0.026*
O6	−0.0503 (3)	0.67518 (13)	0.47084 (12)	0.0527 (6)
O5	0.1734 (3)	0.64124 (12)	0.42671 (10)	0.0428 (6)
N2	0.8262 (2)	0.82271 (12)	0.52275 (10)	0.0233 (5)
H2C	0.8728	0.7876	0.5005	0.028*
O8	0.1626 (3)	0.74917 (15)	0.48804 (11)	0.0530 (6)
C6	0.5101 (3)	0.84150 (15)	0.43238 (12)	0.0258 (6)
C14	0.8130 (3)	0.69224 (14)	0.68843 (12)	0.0244 (6)
C9	0.5394 (3)	0.70458 (14)	0.44370 (12)	0.0257 (6)
H9A	0.6351	0.7081	0.4245	0.031*
H9B	0.4589	0.6943	0.4100	0.031*
C18	0.3568 (3)	0.86310 (14)	0.67420 (11)	0.0229 (6)
C17	0.4615 (3)	0.83124 (14)	0.62995 (11)	0.0217 (5)
O7	0.0320 (4)	0.74181 (15)	0.38604 (11)	0.0672 (8)
C7	0.4224 (3)	0.82719 (17)	0.36663 (12)	0.0326 (7)
H7A	0.4733	0.7894	0.3447	0.049*
H7B	0.4187	0.8717	0.3418	0.049*
H7C	0.3204	0.8115	0.3724	0.049*
C3	0.7870 (3)	0.88481 (15)	0.47783 (12)	0.0278 (6)
H3A	0.7378	0.9235	0.5011	0.033*
C5	0.6758 (3)	0.86021 (15)	0.42156 (12)	0.0268 (6)
H5A	0.7193	0.8170	0.4030	0.032*
H5B	0.6727	0.8989	0.3895	0.032*
C23	0.3032 (4)	0.93478 (16)	0.66577 (14)	0.0359 (7)
H23	0.3329	0.9634	0.6323	0.043*
C15	0.6751 (3)	0.69292 (16)	0.72747 (13)	0.0317 (7)
H15A	0.6786	0.7362	0.7540	0.048*
H15B	0.6770	0.6497	0.7540	0.048*
H15C	0.5830	0.6933	0.6989	0.048*
C10	0.5483 (3)	0.64341 (15)	0.49227 (12)	0.0265 (6)
H10A	0.4521	0.6393	0.5110	0.032*
H10B	0.5679	0.5969	0.4717	0.032*
C1	0.9551 (3)	0.78073 (16)	0.62444 (13)	0.0289 (6)
H1A	0.9963	0.7385	0.6035	0.035*
H1B	1.0269	0.7944	0.6605	0.035*
C2	0.9351 (3)	0.84413 (16)	0.57805 (12)	0.0286 (6)
H2A	0.8965	0.8868	0.5992	0.034*
H2B	1.0327	0.8571	0.5632	0.034*
C13	0.8127 (3)	0.62333 (15)	0.64645 (12)	0.0280 (6)
H13A	0.9016	0.6257	0.6225	0.034*
H13B	0.8261	0.5809	0.6746	0.034*
C8	0.4328 (4)	0.90494 (16)	0.46373 (13)	0.0334 (7)
H8A	0.3276	0.8929	0.4669	0.050*
H8B	0.4390	0.9486	0.4383	0.050*
H8C	0.4830	0.9134	0.5058	0.050*
C19	0.3146 (3)	0.82170 (16)	0.72532 (12)	0.0298 (6)
H19	0.3495	0.7735	0.7311	0.036*
C4	0.9287 (4)	0.91798 (16)	0.45124 (14)	0.0373 (7)
H4A	1.0007	0.9329	0.4861	0.056*
H4B	0.8992	0.9600	0.4251	0.056*
H4C	0.9747	0.8817	0.4258	0.056*
C16	0.9575 (3)	0.69124 (16)	0.73619 (13)	0.0346 (7)
H16A	1.0463	0.6881	0.7131	0.052*
H16B	0.9543	0.6493	0.7640	0.052*
H16C	0.9619	0.7356	0.7613	0.052*
C11	0.6742 (3)	0.60875 (14)	0.59886 (12)	0.0260 (6)
H11	0.5826	0.6189	0.6205	0.031*
C12	0.6712 (4)	0.52789 (16)	0.58023 (15)	0.0436 (8)
H12A	0.5821	0.5181	0.5513	0.065*
H12B	0.6685	0.4981	0.6179	0.065*
H12C	0.7610	0.5163	0.5596	0.065*
C20	0.2205 (3)	0.85191 (18)	0.76787 (13)	0.0365 (7)
H20	0.1938	0.8244	0.8025	0.044*
C22	0.2050 (4)	0.96368 (19)	0.70754 (15)	0.0443 (8)
H22	0.1651	1.0108	0.7008	0.053*
C21	0.1668 (4)	0.92287 (19)	0.75872 (15)	0.0423 (8)
H21	0.1043	0.9432	0.7874	0.051*
O3	0.3369 (3)	0.47611 (10)	0.80658 (9)	0.0360 (5)
H3B	0.3730	0.4465	0.8334	0.054*
O4	0.2469 (3)	0.37507 (12)	0.75552 (10)	0.0530 (7)
C30	0.2927 (3)	0.55960 (15)	0.69518 (13)	0.0303 (6)
H30	0.3393	0.5819	0.7319	0.036*
C29	0.2669 (3)	0.59937 (16)	0.63842 (14)	0.0342 (7)
H29	0.2966	0.6485	0.6370	0.041*
C24	0.2768 (3)	0.44005 (16)	0.75521 (13)	0.0308 (6)
C25	0.2481 (3)	0.48619 (15)	0.69640 (12)	0.0264 (6)
C26	0.1793 (3)	0.45290 (16)	0.64188 (13)	0.0320 (7)
H26	0.1509	0.4036	0.6429	0.038*
C27	0.1524 (4)	0.49276 (18)	0.58565 (13)	0.0362 (7)
H27	0.1046	0.4706	0.5491	0.043*
C28	0.1971 (4)	0.56580 (17)	0.58414 (14)	0.0365 (7)
H28	0.1801	0.5925	0.5463	0.044*

	U11	U22	U33	U12	U13	U23
Ni1	0.02147 (19)	0.01929 (18)	0.01704 (16)	−0.00093 (13)	0.00287 (12)	−0.00228 (13)
Cl1	0.0256 (4)	0.0316 (4)	0.0216 (3)	0.0031 (3)	0.0049 (3)	0.0003 (3)
N3	0.0188 (11)	0.0249 (12)	0.0193 (10)	−0.0003 (9)	0.0048 (8)	0.0003 (9)
N1	0.0241 (12)	0.0218 (12)	0.0198 (10)	0.0002 (9)	0.0028 (9)	−0.0028 (9)
O1	0.0251 (10)	0.0244 (10)	0.0187 (8)	−0.0022 (8)	0.0044 (7)	−0.0002 (7)
O2	0.0289 (11)	0.0240 (10)	0.0233 (9)	−0.0022 (8)	0.0044 (8)	−0.0030 (8)
N4	0.0210 (12)	0.0240 (12)	0.0214 (10)	−0.0026 (9)	0.0035 (9)	−0.0034 (9)
O6	0.0437 (14)	0.0526 (15)	0.0674 (16)	−0.0160 (11)	0.0336 (12)	−0.0186 (12)
O5	0.0486 (14)	0.0445 (13)	0.0372 (11)	0.0199 (11)	0.0146 (10)	0.0008 (10)
N2	0.0251 (12)	0.0221 (12)	0.0231 (11)	−0.0010 (9)	0.0038 (9)	−0.0029 (9)
O8	0.0355 (14)	0.0714 (17)	0.0527 (14)	−0.0149 (12)	0.0072 (11)	−0.0293 (12)
C6	0.0291 (15)	0.0268 (15)	0.0212 (12)	−0.0008 (11)	0.0008 (11)	0.0031 (11)
C14	0.0281 (15)	0.0251 (14)	0.0199 (12)	0.0029 (11)	0.0015 (11)	0.0002 (11)
C9	0.0325 (16)	0.0257 (14)	0.0185 (12)	−0.0047 (12)	−0.0003 (11)	−0.0047 (10)
C18	0.0221 (14)	0.0271 (14)	0.0195 (12)	−0.0008 (11)	0.0013 (10)	−0.0017 (10)
C17	0.0244 (14)	0.0240 (14)	0.0157 (11)	0.0014 (11)	−0.0024 (10)	0.0012 (10)
O7	0.107 (2)	0.0608 (17)	0.0328 (12)	0.0366 (16)	−0.0002 (14)	0.0145 (12)
C7	0.0348 (17)	0.0392 (17)	0.0230 (13)	−0.0028 (13)	−0.0018 (12)	0.0060 (12)
C3	0.0344 (16)	0.0204 (14)	0.0288 (14)	−0.0024 (12)	0.0044 (12)	−0.0001 (11)
C5	0.0337 (16)	0.0236 (14)	0.0234 (13)	−0.0027 (12)	0.0049 (11)	0.0051 (11)
C23	0.0443 (19)	0.0305 (17)	0.0345 (15)	0.0063 (14)	0.0118 (14)	−0.0006 (13)
C15	0.0438 (18)	0.0303 (16)	0.0222 (13)	0.0037 (13)	0.0090 (12)	0.0011 (12)
C10	0.0269 (15)	0.0271 (15)	0.0247 (13)	−0.0062 (11)	−0.0011 (11)	−0.0037 (11)
C1	0.0210 (14)	0.0395 (17)	0.0258 (13)	−0.0041 (12)	0.0006 (11)	0.0002 (12)
C2	0.0248 (15)	0.0353 (16)	0.0251 (13)	−0.0086 (12)	0.0001 (11)	−0.0050 (12)
C13	0.0324 (16)	0.0252 (15)	0.0261 (13)	0.0028 (12)	0.0016 (11)	−0.0012 (11)
C8	0.0375 (18)	0.0328 (16)	0.0293 (14)	0.0075 (13)	0.0000 (12)	0.0042 (12)
C19	0.0336 (17)	0.0337 (16)	0.0222 (13)	−0.0015 (13)	0.0037 (12)	−0.0006 (12)
C4	0.0380 (18)	0.0305 (17)	0.0433 (17)	−0.0106 (13)	0.0030 (14)	0.0065 (14)
C16	0.0395 (18)	0.0364 (17)	0.0259 (14)	0.0026 (14)	−0.0071 (12)	−0.0011 (12)
C11	0.0326 (16)	0.0211 (14)	0.0246 (13)	−0.0028 (11)	0.0040 (11)	0.0009 (11)
C12	0.069 (2)	0.0228 (16)	0.0367 (16)	−0.0051 (15)	−0.0085 (16)	0.0017 (13)
C20	0.0347 (17)	0.050 (2)	0.0263 (14)	−0.0108 (14)	0.0100 (12)	−0.0080 (13)
C22	0.045 (2)	0.0380 (19)	0.0514 (19)	0.0114 (15)	0.0147 (16)	−0.0105 (15)
C21	0.0358 (18)	0.056 (2)	0.0379 (17)	−0.0041 (16)	0.0158 (14)	−0.0217 (15)
O3	0.0535 (14)	0.0279 (11)	0.0243 (10)	0.0026 (10)	−0.0078 (9)	0.0011 (8)
O4	0.093 (2)	0.0331 (13)	0.0289 (11)	−0.0227 (12)	−0.0128 (12)	0.0130 (9)
C30	0.0327 (16)	0.0280 (15)	0.0297 (14)	−0.0047 (12)	0.0005 (12)	0.0028 (12)
C29	0.0327 (17)	0.0253 (15)	0.0455 (17)	0.0006 (12)	0.0085 (13)	0.0099 (13)
C24	0.0365 (17)	0.0299 (16)	0.0255 (14)	−0.0018 (13)	0.0010 (12)	0.0037 (12)
C25	0.0286 (16)	0.0257 (15)	0.0250 (13)	−0.0016 (11)	0.0028 (11)	0.0038 (11)
C26	0.0370 (18)	0.0307 (16)	0.0283 (14)	−0.0033 (13)	0.0032 (12)	0.0034 (12)
C27	0.0414 (19)	0.0423 (18)	0.0244 (13)	−0.0005 (14)	0.0005 (12)	0.0038 (13)
C28	0.0374 (18)	0.0431 (19)	0.0297 (15)	0.0064 (14)	0.0068 (13)	0.0152 (13)

Ni1—N2	2.082 (2)	C15—H15C	0.9600
Ni1—N4	2.091 (2)	C10—H10A	0.9700
Ni1—O2	2.116 (2)	C10—H10B	0.9700
Ni1—N1	2.133 (2)	C1—C2	1.506 (4)
Ni1—N3	2.134 (2)	C1—H1A	0.9700
Ni1—O1	2.212 (2)	C1—H1B	0.9700
Cl1—O7	1.418 (2)	C2—H2A	0.9700
Cl1—O5	1.425 (2)	C2—H2B	0.9700
Cl1—O8	1.429 (2)	C13—C11	1.523 (4)
Cl1—O6	1.433 (2)	C13—H13A	0.9700
N3—C9	1.484 (3)	C13—H13B	0.9700
N3—C6	1.508 (3)	C8—H8A	0.9600
N3—H3C	0.9100	C8—H8B	0.9600
N1—C1	1.485 (3)	C8—H8C	0.9600
N1—C14	1.508 (3)	C19—C20	1.387 (4)
N1—H1C	0.9100	C19—H19	0.9300
O1—C17	1.274 (3)	C4—H4A	0.9600
O2—C17	1.255 (3)	C4—H4B	0.9600
N4—C11	1.485 (3)	C4—H4C	0.9600
N4—C10	1.490 (3)	C16—H16A	0.9600
N4—H4D	0.9100	C16—H16B	0.9600
N2—C2	1.484 (3)	C16—H16C	0.9600
N2—C3	1.487 (3)	C11—C12	1.517 (4)
N2—H2C	0.9100	C11—H11	0.9800
C6—C8	1.518 (4)	C12—H12A	0.9600
C6—C5	1.536 (4)	C12—H12B	0.9600
C6—C7	1.536 (3)	C12—H12C	0.9600
C14—C13	1.529 (4)	C20—C21	1.378 (5)
C14—C15	1.529 (4)	C20—H20	0.9300
C14—C16	1.541 (4)	C22—C21	1.372 (5)
C9—C10	1.503 (4)	C22—H22	0.9300
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	O3—C24	1.326 (3)
C18—C19	1.388 (4)	O3—H3B	0.8200
C18—C23	1.389 (4)	O4—C24	1.208 (3)
C18—C17	1.486 (4)	C30—C25	1.389 (4)
C7—H7A	0.9600	C30—C29	1.392 (4)
C7—H7B	0.9600	C30—H30	0.9300
C7—H7C	0.9600	C29—C28	1.382 (4)
C3—C5	1.526 (4)	C29—H29	0.9300
C3—C4	1.537 (4)	C24—C25	1.492 (4)
C3—H3A	0.9800	C25—C26	1.380 (4)
C5—H5A	0.9700	C26—C27	1.384 (4)
C5—H5B	0.9700	C26—H26	0.9300
C23—C22	1.391 (4)	C27—C28	1.383 (4)
C23—H23	0.9300	C27—H27	0.9300
C15—H15A	0.9600	C28—H28	0.9300
C15—H15B	0.9600
N2—Ni1—N4	104.28 (8)	C14—C15—H15B	109.5
N2—Ni1—O2	156.80 (8)	H15A—C15—H15B	109.5
N4—Ni1—O2	98.91 (8)	C14—C15—H15C	109.5
N2—Ni1—N1	85.74 (8)	H15A—C15—H15C	109.5
N4—Ni1—N1	90.70 (8)	H15B—C15—H15C	109.5
O2—Ni1—N1	94.56 (8)	N4—C10—C9	109.1 (2)
N2—Ni1—N3	91.05 (8)	N4—C10—H10A	109.9
N4—Ni1—N3	84.99 (8)	C9—C10—H10A	109.9
O2—Ni1—N3	90.46 (8)	N4—C10—H10B	109.9
N1—Ni1—N3	173.84 (8)	C9—C10—H10B	109.9
N2—Ni1—O1	96.06 (8)	H10A—C10—H10B	108.3
N4—Ni1—O1	159.39 (8)	N1—C1—C2	110.1 (2)
O2—Ni1—O1	60.82 (7)	N1—C1—H1A	109.6
N1—Ni1—O1	87.49 (7)	C2—C1—H1A	109.6
N3—Ni1—O1	98.09 (7)	N1—C1—H1B	109.6
O7—Cl1—O5	109.69 (14)	C2—C1—H1B	109.6
O7—Cl1—O8	110.04 (18)	H1A—C1—H1B	108.1
O5—Cl1—O8	110.78 (15)	N2—C2—C1	109.4 (2)
O7—Cl1—O6	109.14 (18)	N2—C2—H2A	109.8
O5—Cl1—O6	109.81 (14)	C1—C2—H2A	109.8
O8—Cl1—O6	107.34 (14)	N2—C2—H2B	109.8
C9—N3—C6	113.71 (19)	C1—C2—H2B	109.8
C9—N3—Ni1	104.21 (14)	H2A—C2—H2B	108.2
C6—N3—Ni1	120.59 (15)	C11—C13—C14	118.4 (2)
C9—N3—H3C	105.7	C11—C13—H13A	107.7
C6—N3—H3C	105.7	C14—C13—H13A	107.7
Ni1—N3—H3C	105.7	C11—C13—H13B	107.7
C1—N1—C14	113.5 (2)	C14—C13—H13B	107.7
C1—N1—Ni1	103.69 (15)	H13A—C13—H13B	107.1
C14—N1—Ni1	121.68 (15)	C6—C8—H8A	109.5
C1—N1—H1C	105.6	C6—C8—H8B	109.5
C14—N1—H1C	105.6	H8A—C8—H8B	109.5
Ni1—N1—H1C	105.6	C6—C8—H8C	109.5
C17—O1—Ni1	86.98 (15)	H8A—C8—H8C	109.5
C17—O2—Ni1	91.82 (16)	H8B—C8—H8C	109.5
C11—N4—C10	112.8 (2)	C20—C19—C18	120.2 (3)
C11—N4—Ni1	115.40 (15)	C20—C19—H19	119.9
C10—N4—Ni1	104.85 (15)	C18—C19—H19	119.9
C11—N4—H4D	107.8	C3—C4—H4A	109.5
C10—N4—H4D	107.8	C3—C4—H4B	109.5
Ni1—N4—H4D	107.8	H4A—C4—H4B	109.5
C2—N2—C3	112.9 (2)	C3—C4—H4C	109.5
C2—N2—Ni1	104.20 (15)	H4A—C4—H4C	109.5
C3—N2—Ni1	117.77 (16)	H4B—C4—H4C	109.5
C2—N2—H2C	107.1	C14—C16—H16A	109.5
C3—N2—H2C	107.1	C14—C16—H16B	109.5
Ni1—N2—H2C	107.1	H16A—C16—H16B	109.5
N3—C6—C8	108.1 (2)	C14—C16—H16C	109.5
N3—C6—C5	109.5 (2)	H16A—C16—H16C	109.5
C8—C6—C5	111.6 (2)	H16B—C16—H16C	109.5
N3—C6—C7	111.7 (2)	N4—C11—C12	113.5 (2)
C8—C6—C7	108.0 (2)	N4—C11—C13	110.4 (2)
C5—C6—C7	107.9 (2)	C12—C11—C13	109.2 (2)
N1—C14—C13	110.5 (2)	N4—C11—H11	107.8
N1—C14—C15	107.9 (2)	C12—C11—H11	107.8
C13—C14—C15	110.9 (2)	C13—C11—H11	107.8
N1—C14—C16	111.3 (2)	C11—C12—H12A	109.5
C13—C14—C16	108.7 (2)	C11—C12—H12B	109.5
C15—C14—C16	107.5 (2)	H12A—C12—H12B	109.5
N3—C9—C10	109.3 (2)	C11—C12—H12C	109.5
N3—C9—H9A	109.8	H12A—C12—H12C	109.5
C10—C9—H9A	109.8	H12B—C12—H12C	109.5
N3—C9—H9B	109.8	C21—C20—C19	119.8 (3)
C10—C9—H9B	109.8	C21—C20—H20	120.1
H9A—C9—H9B	108.3	C19—C20—H20	120.1
C19—C18—C23	119.5 (3)	C21—C22—C23	120.2 (3)
C19—C18—C17	120.0 (2)	C21—C22—H22	119.9
C23—C18—C17	120.5 (2)	C23—C22—H22	119.9
O2—C17—O1	120.2 (2)	C22—C21—C20	120.4 (3)
O2—C17—C18	120.2 (2)	C22—C21—H21	119.8
O1—C17—C18	119.6 (2)	C20—C21—H21	119.8
C6—C7—H7A	109.5	C24—O3—H3B	109.5
C6—C7—H7B	109.5	C25—C30—C29	119.3 (3)
H7A—C7—H7B	109.5	C25—C30—H30	120.3
C6—C7—H7C	109.5	C29—C30—H30	120.3
H7A—C7—H7C	109.5	C28—C29—C30	119.9 (3)
H7B—C7—H7C	109.5	C28—C29—H29	120.0
N2—C3—C5	111.1 (2)	C30—C29—H29	120.0
N2—C3—C4	112.3 (2)	O4—C24—O3	123.2 (2)
C5—C3—C4	108.5 (2)	O4—C24—C25	122.2 (2)
N2—C3—H3A	108.3	O3—C24—C25	114.7 (2)
C5—C3—H3A	108.3	C26—C25—C30	120.4 (2)
C4—C3—H3A	108.3	C26—C25—C24	117.7 (2)
C3—C5—C6	119.9 (2)	C30—C25—C24	121.8 (2)
C3—C5—H5A	107.3	C25—C26—C27	120.2 (3)
C6—C5—H5A	107.3	C25—C26—H26	119.9
C3—C5—H5B	107.3	C27—C26—H26	119.9
C6—C5—H5B	107.3	C28—C27—C26	119.6 (3)
H5A—C5—H5B	106.9	C28—C27—H27	120.2
C18—C23—C22	119.8 (3)	C26—C27—H27	120.2
C18—C23—H23	120.1	C29—C28—C27	120.5 (3)
C22—C23—H23	120.1	C29—C28—H28	119.7
C14—C15—H15A	109.5	C27—C28—H28	119.7
N2—Ni1—N3—C9	90.62 (16)	Ni1—N1—C14—C15	−74.8 (2)
N4—Ni1—N3—C9	−13.62 (16)	C1—N1—C14—C16	42.7 (3)
O2—Ni1—N3—C9	−112.53 (16)	Ni1—N1—C14—C16	167.49 (17)
N1—Ni1—N3—C9	32.1 (8)	C6—N3—C9—C10	174.9 (2)
O1—Ni1—N3—C9	−173.10 (15)	Ni1—N3—C9—C10	41.7 (2)
N2—Ni1—N3—C6	−38.55 (19)	Ni1—O2—C17—O1	4.4 (2)
N4—Ni1—N3—C6	−142.79 (19)	Ni1—O2—C17—C18	−174.22 (19)
O2—Ni1—N3—C6	118.30 (18)	Ni1—O1—C17—O2	−4.2 (2)
N1—Ni1—N3—C6	−97.1 (8)	Ni1—O1—C17—C18	174.4 (2)
O1—Ni1—N3—C6	57.73 (19)	C19—C18—C17—O2	36.7 (4)
N2—Ni1—N1—C1	−11.37 (16)	C23—C18—C17—O2	−144.8 (3)
N4—Ni1—N1—C1	92.90 (16)	C19—C18—C17—O1	−141.9 (2)
O2—Ni1—N1—C1	−168.10 (16)	C23—C18—C17—O1	36.6 (4)
N3—Ni1—N1—C1	47.4 (8)	C2—N2—C3—C5	179.6 (2)
O1—Ni1—N1—C1	−107.64 (16)	Ni1—N2—C3—C5	−58.8 (3)
N2—Ni1—N1—C14	−140.56 (19)	C2—N2—C3—C4	57.9 (3)
N4—Ni1—N1—C14	−36.29 (19)	Ni1—N2—C3—C4	179.49 (17)
O2—Ni1—N1—C14	62.71 (19)	N2—C3—C5—C6	70.1 (3)
N3—Ni1—N1—C14	−81.8 (8)	C4—C3—C5—C6	−166.0 (2)
O1—Ni1—N1—C14	123.17 (18)	N3—C6—C5—C3	−64.4 (3)
N2—Ni1—O1—C17	−179.64 (13)	C8—C6—C5—C3	55.3 (3)
N4—Ni1—O1—C17	−8.9 (3)	C7—C6—C5—C3	173.8 (2)
O2—Ni1—O1—C17	2.45 (13)	C19—C18—C23—C22	−1.6 (4)
N1—Ni1—O1—C17	−94.19 (14)	C17—C18—C23—C22	179.9 (3)
N3—Ni1—O1—C17	88.43 (14)	C11—N4—C10—C9	170.4 (2)
N2—Ni1—O2—C17	−7.8 (3)	Ni1—N4—C10—C9	44.0 (2)
N4—Ni1—O2—C17	173.50 (14)	N3—C9—C10—N4	−60.2 (3)
N1—Ni1—O2—C17	82.07 (15)	C14—N1—C1—C2	173.4 (2)
N3—Ni1—O2—C17	−101.50 (14)	Ni1—N1—C1—C2	39.4 (2)
O1—Ni1—O2—C17	−2.48 (13)	C3—N2—C2—C1	173.9 (2)
N2—Ni1—N4—C11	129.24 (18)	Ni1—N2—C2—C1	45.0 (2)
O2—Ni1—N4—C11	−51.27 (18)	N1—C1—C2—N2	−59.7 (3)
N1—Ni1—N4—C11	43.46 (18)	N1—C14—C13—C11	−62.5 (3)
N3—Ni1—N4—C11	−140.95 (18)	C15—C14—C13—C11	57.1 (3)
O1—Ni1—N4—C11	−41.3 (3)	C16—C14—C13—C11	175.1 (2)
N2—Ni1—N4—C10	−106.03 (16)	C23—C18—C19—C20	−0.4 (4)
O2—Ni1—N4—C10	73.46 (16)	C17—C18—C19—C20	178.1 (2)
N1—Ni1—N4—C10	168.18 (16)	C10—N4—C11—C12	51.8 (3)
N3—Ni1—N4—C10	−16.22 (16)	Ni1—N4—C11—C12	172.2 (2)
O1—Ni1—N4—C10	83.5 (3)	C10—N4—C11—C13	174.8 (2)
N4—Ni1—N2—C2	−107.64 (16)	Ni1—N4—C11—C13	−64.7 (2)
O2—Ni1—N2—C2	73.6 (3)	C14—C13—C11—N4	74.4 (3)
N1—Ni1—N2—C2	−18.00 (16)	C14—C13—C11—C12	−160.1 (2)
N3—Ni1—N2—C2	167.26 (16)	C18—C19—C20—C21	1.1 (4)
O1—Ni1—N2—C2	69.01 (16)	C18—C23—C22—C21	3.1 (5)
N4—Ni1—N2—C3	126.38 (17)	C23—C22—C21—C20	−2.5 (5)
O2—Ni1—N2—C3	−52.3 (3)	C19—C20—C21—C22	0.4 (5)
N1—Ni1—N2—C3	−143.98 (18)	C25—C30—C29—C28	0.2 (4)
N3—Ni1—N2—C3	41.29 (18)	C29—C30—C25—C26	0.2 (4)
O1—Ni1—N2—C3	−56.96 (18)	C29—C30—C25—C24	178.1 (3)
C9—N3—C6—C8	163.9 (2)	O4—C24—C25—C26	2.7 (5)
Ni1—N3—C6—C8	−71.2 (2)	O3—C24—C25—C26	−177.2 (3)
C9—N3—C6—C5	−74.3 (3)	O4—C24—C25—C30	−175.3 (3)
Ni1—N3—C6—C5	50.6 (3)	O3—C24—C25—C30	4.8 (4)
C9—N3—C6—C7	45.2 (3)	C30—C25—C26—C27	−0.8 (4)
Ni1—N3—C6—C7	170.07 (17)	C24—C25—C26—C27	−178.8 (3)
C1—N1—C14—C13	−78.2 (3)	C25—C26—C27—C28	1.0 (5)
Ni1—N1—C14—C13	46.7 (3)	C30—C29—C28—C27	0.0 (5)
C1—N1—C14—C15	160.4 (2)	C26—C27—C28—C29	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O4i	0.91	2.07	2.970 (3)	171
N4—H4D···O6ii	0.91	2.13	3.001 (3)	161
O3—H3B···O1iii	0.82	1.87	2.691 (3)	174
N3—H3C···O8	0.91	2.22	3.108 (3)	166
N2—H2C···O6ii	0.91	2.25	3.123 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O4i	0.91	2.07	2.970 (3)	171
N4—H4D⋯O6ii	0.91	2.13	3.001 (3)	161
O3—H3B⋯O1iii	0.82	1.87	2.691 (3)	174
N3—H3C⋯O8	0.91	2.22	3.108 (3)	166
N2—H2C⋯O6ii	0.91	2.25	3.123 (3)	160

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