A new nickel(II) complex, [NiL]·CH₃OH, where H₂L is 2-phenyl-3,10,18,21-tetra­azatetra­cyclo­[20.4.0.0^4,9.0^12,17]hexa­cosa-2,10,12,14,16,22,24,26-octa­ene-19,20-dionate(2−)

In the title compound, [2-phenyl-3,10,18,21-tetra­azatetracyclo­[20.4.0.0^4,9.0^12,17]hexa­cosa-2,10,12,14,16,22,24,26-octaene-19,20-dionato(2−)]copper(II) methanol solvate, [Cu(C₃₄H₂₈N₄O₂)]·CH₃OH, the Ni^II atom is coordinated by four N atoms from the doubly deprotonated tetra­aza ligand, L²⁻, in a square-planar coordination geometry. O—H...O hydrogen bonds link the complex to the methanol solvent mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.104
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H19A   ..  O3      ..       2.99 Ang.

Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.54 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O3      ..       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  N2      ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O3      ..       2.65 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  O3      ..       3.87 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N3  -NI1 -N1  -C1    139.20  1.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N3  -NI1 -N1  -C34   -44.10  1.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            N4  -NI1 -N2  -C2     50.40  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N4  -NI1 -N2  -C3   -122.80  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            N1  -NI1 -N3  -C9    -89.60  1.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -NI1 -N3  -C16    78.10  1.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            N2  -NI1 -N4  -C22   -98.00  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            N2  -NI1 -N4  -C21    74.90  0.80   1.555   1.555   1.555   1.555
PLAT728_ALERT_1_C D-H..A  Calc      141.00, Rep      143.00 Dev...       2.00 Deg.
              O3   -H3   -O2      1.555   1.555   1.565

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  13 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

[2-phenyl-3,10,18,21-tetraazatetracyclo[20.4.0.0^4,9.0^12,17]hexacosa- 2,10,12,14,16,22,24,26-octaene-19,20-dionato(2-)]copper(II) methanol solvate

Crystal data

[Ni(C34H28N4O2)]·CH4O	Z = 2
Mr = 615.36	F(000) = 644
Triclinic, P1	Dx = 1.370 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1790 (15) Å	Cell parameters from 2957 reflections
b = 12.5659 (18) Å	θ = 2.5–25.6°
c = 12.8305 (19) Å	µ = 0.69 mm^−1
α = 71.764 (2)°	T = 294 K
β = 83.782 (3)°	Block, red
γ = 73.156 (2)°	0.26 × 0.20 × 0.14 mm
V = 1491.5 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5216 independent reflections
Radiation source: fine-focus sealed tube	3953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.750, Tmax = 0.908	k = −14→14
7640 measured reflections	l = −15→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.188P] where P = (Fo^2 + 2Fc^2)/3
5216 reflections	(Δ/σ)max = 0.001
390 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.60547 (3)	−0.01025 (3)	0.77380 (3)	0.03074 (12)
O1	0.8190 (2)	−0.32335 (16)	0.79015 (18)	0.0502 (5)
O2	0.5540 (2)	−0.31608 (17)	0.8583 (2)	0.0610 (6)
N1	0.7675 (2)	−0.12777 (17)	0.78163 (18)	0.0335 (5)
N2	0.5251 (2)	−0.12491 (17)	0.85841 (17)	0.0310 (5)
N3	0.4450 (2)	0.11251 (17)	0.76998 (19)	0.0337 (5)
N4	0.6842 (2)	0.09788 (17)	0.67464 (17)	0.0314 (5)
C1	0.7417 (3)	−0.2326 (2)	0.8005 (2)	0.0363 (6)
C2	0.5933 (3)	−0.2284 (2)	0.8418 (2)	0.0386 (7)
C3	0.4040 (3)	−0.1099 (2)	0.9215 (2)	0.0321 (6)
C4	0.3642 (3)	−0.2065 (2)	0.9926 (2)	0.0392 (7)
H4	0.4157	−0.2812	0.9935	0.047*
C5	0.2502 (3)	−0.1923 (3)	1.0610 (2)	0.0458 (7)
H5	0.2250	−0.2574	1.1065	0.055*
C6	0.1736 (3)	−0.0830 (3)	1.0624 (2)	0.0489 (8)
H6	0.0969	−0.0738	1.1086	0.059*
C7	0.2113 (3)	0.0124 (3)	0.9951 (2)	0.0427 (7)
H7	0.1607	0.0859	0.9985	0.051*
C8	0.3241 (3)	0.0034 (2)	0.9208 (2)	0.0326 (6)
C9	0.3449 (3)	0.1114 (2)	0.8427 (2)	0.0329 (6)
C10	0.2456 (3)	0.2231 (2)	0.8513 (2)	0.0351 (6)
C11	0.1097 (3)	0.2573 (3)	0.8189 (3)	0.0463 (8)
H11	0.0776	0.2101	0.7905	0.056*
C12	0.0225 (3)	0.3607 (3)	0.8286 (3)	0.0523 (8)
H12	−0.0673	0.3843	0.8046	0.063*
C13	0.0684 (4)	0.4288 (3)	0.8738 (3)	0.0587 (9)
H13	0.0089	0.4979	0.8813	0.070*
C14	0.2011 (4)	0.3957 (3)	0.9079 (3)	0.0568 (9)
H14	0.2312	0.4423	0.9385	0.068*
C15	0.2908 (3)	0.2925 (2)	0.8968 (2)	0.0445 (7)
H15	0.3809	0.2702	0.9199	0.053*
C16	0.4576 (3)	0.2239 (2)	0.6852 (3)	0.0437 (7)
H16	0.4875	0.2696	0.7228	0.052*
C17	0.3346 (3)	0.3029 (3)	0.6177 (3)	0.0744 (13)
H17A	0.2596	0.3262	0.6664	0.089*
H17B	0.3577	0.3726	0.5710	0.089*
C18	0.2885 (4)	0.2450 (4)	0.5475 (4)	0.0969 (17)
H18A	0.2076	0.2977	0.5076	0.116*
H18B	0.2640	0.1759	0.5939	0.116*
C19	0.4015 (4)	0.2114 (3)	0.4665 (3)	0.0828 (13)
H19A	0.4194	0.2811	0.4151	0.099*
H19B	0.3720	0.1698	0.4253	0.099*
C20	0.5328 (4)	0.1346 (3)	0.5274 (3)	0.0567 (9)
H20A	0.5194	0.0590	0.5680	0.068*
H20B	0.6070	0.1229	0.4744	0.068*
C21	0.5731 (3)	0.1879 (2)	0.6067 (2)	0.0370 (7)
H21	0.6065	0.2552	0.5652	0.044*
C22	0.8126 (3)	0.0973 (2)	0.6534 (2)	0.0316 (6)
C23	0.8478 (3)	0.2048 (2)	0.5811 (2)	0.0334 (6)
C24	0.8190 (3)	0.3003 (2)	0.6197 (2)	0.0398 (7)
H24	0.7789	0.2961	0.6890	0.048*
C25	0.8492 (3)	0.4019 (2)	0.5566 (3)	0.0460 (7)
H25	0.8292	0.4658	0.5833	0.055*
C26	0.9088 (3)	0.4083 (3)	0.4545 (3)	0.0490 (8)
H26	0.9292	0.4766	0.4118	0.059*
C27	0.9383 (3)	0.3139 (3)	0.4151 (3)	0.0531 (8)
H27	0.9786	0.3185	0.3458	0.064*
C28	0.9084 (3)	0.2124 (3)	0.4780 (2)	0.0467 (8)
H28	0.9290	0.1487	0.4511	0.056*
C29	0.9228 (3)	−0.0046 (2)	0.7049 (2)	0.0336 (6)
C30	1.0587 (3)	0.0056 (3)	0.6926 (2)	0.0426 (7)
H30	1.0747	0.0767	0.6531	0.051*
C31	1.1674 (3)	−0.0867 (3)	0.7375 (3)	0.0526 (8)
H31	1.2562	−0.0785	0.7271	0.063*
C32	1.1441 (3)	−0.1919 (3)	0.7986 (3)	0.0530 (8)
H32	1.2175	−0.2541	0.8304	0.064*
C33	1.0137 (3)	−0.2055 (3)	0.8126 (2)	0.0444 (7)
H33	1.0002	−0.2769	0.8543	0.053*
C34	0.9000 (3)	−0.1138 (2)	0.7651 (2)	0.0339 (6)
O3	0.6704 (4)	0.4966 (3)	0.7656 (4)	0.1138 (12)
H3	0.6726	0.5560	0.7784	0.171*
C35	0.5324 (6)	0.4983 (4)	0.7570 (6)	0.133 (2)
H35A	0.5113	0.4345	0.8138	0.199*
H35B	0.5196	0.4913	0.6866	0.199*
H35C	0.4727	0.5703	0.7646	0.199*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0287 (2)	0.02421 (19)	0.0351 (2)	−0.00513 (14)	0.00141 (14)	−0.00554 (14)
O1	0.0486 (12)	0.0321 (11)	0.0651 (14)	−0.0041 (9)	0.0109 (11)	−0.0181 (10)
O2	0.0644 (15)	0.0402 (12)	0.0882 (18)	−0.0253 (11)	0.0259 (13)	−0.0318 (12)
N1	0.0321 (12)	0.0276 (12)	0.0368 (13)	−0.0041 (10)	0.0022 (10)	−0.0085 (10)
N2	0.0296 (12)	0.0252 (11)	0.0345 (13)	−0.0060 (9)	0.0040 (10)	−0.0066 (10)
N3	0.0294 (12)	0.0246 (11)	0.0415 (13)	−0.0056 (9)	0.0031 (10)	−0.0050 (10)
N4	0.0296 (12)	0.0275 (11)	0.0341 (12)	−0.0067 (9)	0.0009 (10)	−0.0063 (10)
C1	0.0429 (16)	0.0283 (15)	0.0343 (16)	−0.0049 (13)	0.0012 (13)	−0.0094 (12)
C2	0.0433 (17)	0.0327 (15)	0.0392 (17)	−0.0120 (13)	0.0024 (13)	−0.0094 (13)
C3	0.0323 (14)	0.0339 (14)	0.0298 (14)	−0.0116 (12)	−0.0027 (12)	−0.0061 (12)
C4	0.0402 (16)	0.0378 (15)	0.0376 (16)	−0.0146 (13)	−0.0005 (13)	−0.0046 (13)
C5	0.0543 (19)	0.0494 (18)	0.0354 (17)	−0.0272 (16)	0.0046 (14)	−0.0047 (14)
C6	0.0469 (18)	0.066 (2)	0.0372 (17)	−0.0245 (17)	0.0150 (14)	−0.0171 (16)
C7	0.0420 (17)	0.0462 (17)	0.0413 (17)	−0.0104 (14)	0.0067 (14)	−0.0188 (14)
C8	0.0286 (14)	0.0370 (15)	0.0336 (15)	−0.0088 (12)	0.0001 (12)	−0.0129 (12)
C9	0.0292 (14)	0.0333 (14)	0.0375 (16)	−0.0069 (12)	−0.0030 (12)	−0.0131 (12)
C10	0.0311 (14)	0.0306 (14)	0.0407 (16)	−0.0029 (12)	0.0022 (12)	−0.0124 (12)
C11	0.0323 (16)	0.0488 (18)	0.058 (2)	−0.0098 (14)	0.0028 (14)	−0.0190 (16)
C12	0.0340 (16)	0.0509 (19)	0.058 (2)	0.0017 (14)	0.0031 (15)	−0.0109 (17)
C13	0.058 (2)	0.0367 (17)	0.066 (2)	0.0070 (16)	0.0072 (18)	−0.0147 (17)
C14	0.069 (2)	0.0388 (17)	0.063 (2)	−0.0070 (16)	−0.0035 (18)	−0.0219 (16)
C15	0.0444 (17)	0.0387 (16)	0.0492 (19)	−0.0081 (14)	−0.0068 (14)	−0.0124 (14)
C16	0.0375 (16)	0.0245 (14)	0.057 (2)	−0.0038 (12)	0.0030 (14)	−0.0014 (13)
C17	0.0385 (19)	0.056 (2)	0.086 (3)	0.0026 (17)	0.0058 (19)	0.023 (2)
C18	0.047 (2)	0.095 (3)	0.111 (4)	−0.025 (2)	−0.030 (3)	0.037 (3)
C19	0.098 (3)	0.070 (3)	0.075 (3)	−0.032 (2)	−0.052 (3)	0.010 (2)
C20	0.071 (2)	0.0490 (19)	0.047 (2)	−0.0160 (17)	−0.0153 (17)	−0.0053 (16)
C21	0.0338 (15)	0.0300 (14)	0.0395 (16)	−0.0093 (12)	−0.0015 (13)	0.0012 (12)
C22	0.0326 (15)	0.0344 (14)	0.0321 (15)	−0.0111 (12)	0.0037 (12)	−0.0154 (12)
C23	0.0306 (14)	0.0354 (15)	0.0363 (16)	−0.0113 (12)	0.0033 (12)	−0.0127 (12)
C24	0.0432 (17)	0.0420 (16)	0.0376 (16)	−0.0151 (13)	0.0059 (13)	−0.0154 (13)
C25	0.0527 (19)	0.0369 (16)	0.0509 (19)	−0.0154 (14)	−0.0009 (15)	−0.0134 (14)
C26	0.0479 (18)	0.0450 (18)	0.052 (2)	−0.0227 (15)	0.0030 (15)	−0.0044 (15)
C27	0.061 (2)	0.060 (2)	0.0413 (18)	−0.0276 (17)	0.0140 (16)	−0.0137 (16)
C28	0.056 (2)	0.0461 (17)	0.0473 (19)	−0.0233 (15)	0.0126 (15)	−0.0232 (15)
C29	0.0299 (14)	0.0373 (15)	0.0376 (16)	−0.0077 (12)	0.0006 (12)	−0.0183 (13)
C30	0.0383 (16)	0.0519 (18)	0.0468 (18)	−0.0171 (14)	0.0012 (14)	−0.0237 (15)
C31	0.0338 (17)	0.071 (2)	0.061 (2)	−0.0115 (16)	−0.0048 (15)	−0.0322 (19)
C32	0.0385 (18)	0.059 (2)	0.058 (2)	0.0018 (15)	−0.0133 (15)	−0.0227 (17)
C33	0.0435 (18)	0.0408 (16)	0.0480 (18)	−0.0040 (14)	−0.0098 (14)	−0.0159 (14)
C34	0.0304 (15)	0.0380 (15)	0.0347 (15)	−0.0046 (12)	0.0001 (12)	−0.0173 (13)
O3	0.116 (3)	0.074 (2)	0.171 (4)	−0.0216 (19)	0.019 (3)	−0.074 (2)
C35	0.148 (5)	0.083 (3)	0.193 (7)	−0.054 (4)	0.034 (5)	−0.069 (4)

Geometric parameters (Å, º)

Ni1—N1	1.855 (2)	C17—C18	1.504 (6)
Ni1—N2	1.854 (2)	C17—H17A	0.9700
Ni1—N3	1.887 (2)	C17—H17B	0.9700
Ni1—N4	1.854 (2)	C18—C19	1.521 (6)
O1—C1	1.220 (3)	C18—H18A	0.9700
O2—C2	1.228 (3)	C18—H18B	0.9700
N1—C1	1.360 (3)	C19—C20	1.528 (5)
N1—C34	1.396 (3)	C19—H19A	0.9700
N2—C2	1.356 (3)	C19—H19B	0.9700
N2—C3	1.399 (3)	C20—C21	1.527 (4)
N3—C9	1.305 (3)	C20—H20A	0.9700
N3—C16	1.510 (3)	C20—H20B	0.9700
N4—C22	1.304 (3)	C21—H21	0.9800
N4—C21	1.475 (3)	C22—C29	1.461 (4)
C1—C2	1.538 (4)	C22—C23	1.496 (3)
C3—C4	1.408 (3)	C23—C24	1.382 (4)
C3—C8	1.418 (3)	C23—C28	1.384 (4)
C4—C5	1.381 (4)	C24—C25	1.380 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.374 (4)	C25—C26	1.372 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.370 (4)	C26—C27	1.374 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.413 (4)	C27—C28	1.378 (4)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.470 (4)	C28—H28	0.9300
C9—C10	1.501 (3)	C29—C30	1.414 (4)
C10—C15	1.387 (4)	C29—C34	1.419 (4)
C10—C11	1.393 (4)	C30—C31	1.370 (4)
C11—C12	1.378 (4)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.383 (4)
C12—C13	1.374 (5)	C31—H31	0.9300
C12—H12	0.9300	C32—C33	1.373 (4)
C13—C14	1.370 (5)	C32—H32	0.9300
C13—H13	0.9300	C33—C34	1.407 (4)
C14—C15	1.391 (4)	C33—H33	0.9300
C14—H14	0.9300	O3—C35	1.414 (6)
C15—H15	0.9300	O3—H3	0.8200
C16—C17	1.509 (4)	C35—H35A	0.9600
C16—C21	1.524 (4)	C35—H35B	0.9600
C16—H16	0.9800	C35—H35C	0.9600
N1—Ni1—N3	177.07 (10)	C16—C17—H17B	109.2
N2—Ni1—N1	86.88 (9)	H17A—C17—H17B	107.9
N2—Ni1—N3	94.35 (9)	C17—C18—C19	110.8 (3)
N2—Ni1—N4	172.89 (10)	C17—C18—H18A	109.5
N4—Ni1—N1	91.56 (9)	C19—C18—H18A	109.5
N4—Ni1—N3	87.55 (9)	C17—C18—H18B	109.5
C1—N1—C34	122.6 (2)	C19—C18—H18B	109.5
C1—N1—Ni1	111.07 (17)	H18A—C18—H18B	108.1
C34—N1—Ni1	126.23 (17)	C18—C19—C20	110.3 (3)
C2—N2—C3	122.7 (2)	C18—C19—H19A	109.6
C2—N2—Ni1	109.74 (17)	C20—C19—H19A	109.6
C3—N2—Ni1	127.20 (17)	C18—C19—H19B	109.6
C9—N3—C16	121.6 (2)	C20—C19—H19B	109.6
C9—N3—Ni1	125.79 (18)	H19A—C19—H19B	108.1
C16—N3—Ni1	111.49 (16)	C21—C20—C19	112.1 (3)
C22—N4—C21	121.4 (2)	C21—C20—H20A	109.2
C22—N4—Ni1	130.84 (18)	C19—C20—H20A	109.2
C21—N4—Ni1	107.35 (16)	C21—C20—H20B	109.2
O1—C1—N1	129.0 (3)	C19—C20—H20B	109.2
O1—C1—C2	119.8 (2)	H20A—C20—H20B	107.9
N1—C1—C2	111.3 (2)	N4—C21—C16	106.8 (2)
O2—C2—N2	129.2 (3)	N4—C21—C20	107.2 (2)
O2—C2—C1	118.4 (2)	C16—C21—C20	113.9 (2)
N2—C2—C1	112.4 (2)	N4—C21—H21	109.6
N2—C3—C4	120.8 (2)	C16—C21—H21	109.6
N2—C3—C8	120.3 (2)	C20—C21—H21	109.6
C4—C3—C8	118.7 (2)	N4—C22—C29	120.8 (2)
C5—C4—C3	121.1 (3)	N4—C22—C23	119.7 (2)
C5—C4—H4	119.4	C29—C22—C23	119.4 (2)
C3—C4—H4	119.4	C24—C23—C28	118.8 (2)
C6—C5—C4	120.6 (3)	C24—C23—C22	118.1 (2)
C6—C5—H5	119.7	C28—C23—C22	123.1 (2)
C4—C5—H5	119.7	C25—C24—C23	120.8 (3)
C7—C6—C5	119.4 (3)	C25—C24—H24	119.6
C7—C6—H6	120.3	C23—C24—H24	119.6
C5—C6—H6	120.3	C26—C25—C24	119.8 (3)
C6—C7—C8	122.6 (3)	C26—C25—H25	120.1
C6—C7—H7	118.7	C24—C25—H25	120.1
C8—C7—H7	118.7	C25—C26—C27	120.1 (3)
C7—C8—C3	117.6 (2)	C25—C26—H26	119.9
C7—C8—C9	118.0 (2)	C27—C26—H26	119.9
C3—C8—C9	124.3 (2)	C26—C27—C28	120.2 (3)
N3—C9—C8	122.8 (2)	C26—C27—H27	119.9
N3—C9—C10	120.7 (2)	C28—C27—H27	119.9
C8—C9—C10	116.6 (2)	C27—C28—C23	120.4 (3)
C15—C10—C11	119.1 (3)	C27—C28—H28	119.8
C15—C10—C9	118.2 (2)	C23—C28—H28	119.8
C11—C10—C9	122.7 (2)	C30—C29—C34	118.6 (2)
C12—C11—C10	120.5 (3)	C30—C29—C22	118.4 (2)
C12—C11—H11	119.8	C34—C29—C22	123.1 (2)
C10—C11—H11	119.8	C31—C30—C29	121.6 (3)
C13—C12—C11	119.9 (3)	C31—C30—H30	119.2
C13—C12—H12	120.1	C29—C30—H30	119.2
C11—C12—H12	120.1	C30—C31—C32	119.6 (3)
C14—C13—C12	120.6 (3)	C30—C31—H31	120.2
C14—C13—H13	119.7	C32—C31—H31	120.2
C12—C13—H13	119.7	C33—C32—C31	120.7 (3)
C13—C14—C15	120.1 (3)	C33—C32—H32	119.7
C13—C14—H14	119.9	C31—C32—H32	119.7
C15—C14—H14	119.9	C32—C33—C34	121.4 (3)
C10—C15—C14	119.9 (3)	C32—C33—H33	119.3
C10—C15—H15	120.1	C34—C33—H33	119.3
C14—C15—H15	120.1	N1—C34—C33	120.9 (2)
C17—C16—N3	119.4 (2)	N1—C34—C29	120.8 (2)
C17—C16—C21	108.0 (3)	C33—C34—C29	118.2 (2)
N3—C16—C21	106.0 (2)	C35—O3—H3	109.5
C17—C16—H16	107.7	O3—C35—H35A	109.5
N3—C16—H16	107.7	O3—C35—H35B	109.5
C21—C16—H16	107.7	H35A—C35—H35B	109.5
C18—C17—C16	112.2 (3)	O3—C35—H35C	109.5
C18—C17—H17A	109.2	H35A—C35—H35C	109.5
C16—C17—H17A	109.2	H35B—C35—H35C	109.5
C18—C17—H17B	109.2
N2—Ni1—N1—C1	24.41 (19)	C15—C10—C11—C12	2.1 (4)
N4—Ni1—N1—C1	−148.65 (19)	C9—C10—C11—C12	179.9 (3)
N3—Ni1—N1—C1	139.2 (18)	C10—C11—C12—C13	−2.1 (5)
N2—Ni1—N1—C34	−158.8 (2)	C11—C12—C13—C14	1.0 (5)
N4—Ni1—N1—C34	28.1 (2)	C12—C13—C14—C15	0.1 (5)
N3—Ni1—N1—C34	−44.1 (19)	C11—C10—C15—C14	−1.0 (4)
N4—Ni1—N2—C2	50.4 (8)	C9—C10—C15—C14	−178.9 (3)
N1—Ni1—N2—C2	−27.00 (19)	C13—C14—C15—C10	−0.1 (5)
N3—Ni1—N2—C2	155.66 (19)	C9—N3—C16—C17	−50.3 (4)
N4—Ni1—N2—C3	−122.8 (7)	Ni1—N3—C16—C17	141.3 (3)
N1—Ni1—N2—C3	159.7 (2)	C9—N3—C16—C21	−172.3 (2)
N3—Ni1—N2—C3	−17.6 (2)	Ni1—N3—C16—C21	19.4 (3)
N2—Ni1—N3—C9	25.0 (2)	N3—C16—C17—C18	−62.6 (4)
N4—Ni1—N3—C9	−161.9 (2)	C21—C16—C17—C18	58.3 (4)
N1—Ni1—N3—C9	−89.6 (18)	C16—C17—C18—C19	−61.1 (4)
N2—Ni1—N3—C16	−167.28 (19)	C17—C18—C19—C20	55.6 (4)
N4—Ni1—N3—C16	5.85 (19)	C18—C19—C20—C21	−51.0 (4)
N1—Ni1—N3—C16	78.1 (19)	C22—N4—C21—C16	−137.8 (2)
N2—Ni1—N4—C22	−98.0 (8)	Ni1—N4—C21—C16	48.4 (2)
N1—Ni1—N4—C22	−20.9 (2)	C22—N4—C21—C20	99.7 (3)
N3—Ni1—N4—C22	156.3 (2)	Ni1—N4—C21—C20	−74.1 (2)
N2—Ni1—N4—C21	74.9 (8)	C17—C16—C21—N4	−171.9 (2)
N1—Ni1—N4—C21	152.10 (18)	N3—C16—C21—N4	−42.9 (3)
N3—Ni1—N4—C21	−30.69 (18)	C17—C16—C21—C20	−53.8 (3)
C34—N1—C1—O1	−12.2 (5)	N3—C16—C21—C20	75.2 (3)
Ni1—N1—C1—O1	164.7 (3)	C19—C20—C21—N4	169.7 (3)
C34—N1—C1—C2	166.9 (2)	C19—C20—C21—C16	51.8 (4)
Ni1—N1—C1—C2	−16.2 (3)	C21—N4—C22—C29	−166.4 (2)
C3—N2—C2—O2	14.6 (5)	Ni1—N4—C22—C29	5.7 (4)
Ni1—N2—C2—O2	−159.0 (3)	C21—N4—C22—C23	17.4 (4)
C3—N2—C2—C1	−162.9 (2)	Ni1—N4—C22—C23	−170.49 (18)
Ni1—N2—C2—C1	23.5 (3)	N4—C22—C23—C24	68.0 (3)
O1—C1—C2—O2	−3.5 (4)	C29—C22—C23—C24	−108.2 (3)
N1—C1—C2—O2	177.3 (3)	N4—C22—C23—C28	−112.4 (3)
O1—C1—C2—N2	174.2 (3)	C29—C22—C23—C28	71.3 (4)
N1—C1—C2—N2	−4.9 (3)	C28—C23—C24—C25	0.4 (4)
C2—N2—C3—C4	15.6 (4)	C22—C23—C24—C25	180.0 (2)
Ni1—N2—C3—C4	−171.95 (19)	C23—C24—C25—C26	−0.2 (4)
C2—N2—C3—C8	−168.9 (2)	C24—C25—C26—C27	0.0 (5)
Ni1—N2—C3—C8	3.6 (4)	C25—C26—C27—C28	0.0 (5)
N2—C3—C4—C5	175.3 (3)	C26—C27—C28—C23	0.3 (5)
C8—C3—C4—C5	−0.3 (4)	C24—C23—C28—C27	−0.5 (4)
C3—C4—C5—C6	−0.9 (4)	C22—C23—C28—C27	180.0 (3)
C4—C5—C6—C7	0.0 (5)	N4—C22—C29—C30	−170.3 (2)
C5—C6—C7—C8	2.2 (4)	C23—C22—C29—C30	5.9 (4)
C6—C7—C8—C3	−3.4 (4)	N4—C22—C29—C34	10.6 (4)
C6—C7—C8—C9	172.4 (3)	C23—C22—C29—C34	−173.2 (2)
N2—C3—C8—C7	−173.3 (2)	C34—C29—C30—C31	−0.2 (4)
C4—C3—C8—C7	2.3 (4)	C22—C29—C30—C31	−179.3 (3)
N2—C3—C8—C9	11.3 (4)	C29—C30—C31—C32	−1.5 (5)
C4—C3—C8—C9	−173.1 (2)	C30—C31—C32—C33	1.4 (5)
C16—N3—C9—C8	175.3 (2)	C31—C32—C33—C34	0.4 (5)
Ni1—N3—C9—C8	−18.1 (4)	C1—N1—C34—C33	−28.6 (4)
C16—N3—C9—C10	−5.7 (4)	Ni1—N1—C34—C33	155.0 (2)
Ni1—N3—C9—C10	160.85 (19)	C1—N1—C34—C29	154.9 (3)
C7—C8—C9—N3	−179.2 (3)	Ni1—N1—C34—C29	−21.6 (4)
C3—C8—C9—N3	−3.8 (4)	C32—C33—C34—N1	−178.7 (3)
C7—C8—C9—C10	1.7 (4)	C32—C33—C34—C29	−2.1 (4)
C3—C8—C9—C10	177.2 (2)	C30—C29—C34—N1	178.6 (2)
N3—C9—C10—C15	−73.2 (3)	C22—C29—C34—N1	−2.4 (4)
C8—C9—C10—C15	105.8 (3)	C30—C29—C34—C33	1.9 (4)
N3—C9—C10—C11	108.9 (3)	C22—C29—C34—C33	−179.0 (3)
C8—C9—C10—C11	−72.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^i	0.82	2.17	2.862 (3)	143
O3—H3···O1^i	0.82	2.46	3.169 (4)	145
C5—H5···O3^ii	0.93	2.88	3.675 (5)	144
C15—H15···N2^ii	0.93	2.94	3.558 (4)	125
C12—H12···O3^iii	0.93	2.65	3.556 (5)	164
C13—H13···O1^iv	0.93	2.55	3.349 (4)	145
C19—H19A···O3^v	0.97	2.99	3.865 (5)	151
C27—H27···O1^vi	0.93	2.55	3.409 (4)	153
C35—H35C···O2^i	0.96	2.48	3.074 (5)	120

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