Bis{4-[(Z)-(2,4-dimethyl­phenyl­amino)phenyl­methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onato-κ²N,O}(ethanol-κO)nickel(II)

The Ni^II atom in the title compound, [Ni(C₂₅H₂₂N₃O)₂(C₂H₆O)], is chelated by two deprotonated 4-[(Z)-(2,4-dimethyl­phenyl­amino)phenyl­methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one ligands through their amide N and carbonyl O atoms and coordinated by an ethanol mol­ecule in a five-coordinate trigonal–bipyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.151
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.07 Ratio

Author Response: The ethanol is somewhat disordered, but the disorder was not treated.

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C51     ..      19.01 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT731_ALERT_1_C Bond    Calc   1.476(12), Rep    1.478(5) ......       2.40 su-Ra
              C51  -C52     1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis{4-[(Z)-(2,4-dimethylphenylamino)phenylmethylene]-3-methyl-1-phenyl-1H- pyrazol-5(4H)-onatoκ²N,O}(ethanol-κO)nickel(II)

Crystal data

[Ni(C25H22N3O)2(C2H6O)]	F(000) = 1824
Mr = 865.69	Dx = 1.262 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6181 reflections
a = 24.478 (1) Å	θ = 2.2–21.3°
b = 14.8835 (6) Å	µ = 0.48 mm^−1
c = 12.6757 (5) Å	T = 295 K
β = 99.366 (1)°	Block, green
V = 4556.4 (3) Å^3	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	8022 independent reflections
Radiation source: fine-focus sealed tube	5347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
ω and φ scans	θmax = 25.0°, θmin = 0.8°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −29→29
Tmin = 0.911, Tmax = 0.954	k = −17→17
43522 measured reflections	l = −15→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0811P)^2] where P = (Fo^2 + 2Fc^2)/3
8022 reflections	(Δ/σ)max = 0.001
565 parameters	Δρmax = 0.60 e Å^−3
20 restraints	Δρmin = −0.58 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.735525 (17)	0.47477 (3)	0.56797 (3)	0.04315 (16)
O1	0.69442 (10)	0.37465 (15)	0.62216 (18)	0.0518 (6)
O2	0.77269 (9)	0.55354 (16)	0.47710 (18)	0.0510 (6)
O3	0.71478 (16)	0.3998 (2)	0.4273 (2)	0.1100 (13)
H3O	0.7029	0.3471	0.4359	0.132*
N1	0.66967 (12)	0.30073 (19)	0.7689 (2)	0.0520 (7)
N2	0.69085 (13)	0.2884 (2)	0.8777 (2)	0.0578 (8)
N3	0.79942 (11)	0.46261 (17)	0.6898 (2)	0.0451 (7)
N4	0.81215 (11)	0.69196 (19)	0.4499 (2)	0.0517 (7)
N5	0.80716 (12)	0.7817 (2)	0.4793 (2)	0.0576 (8)
N6	0.69457 (10)	0.57912 (17)	0.6216 (2)	0.0419 (6)
C1	0.61568 (16)	0.2695 (2)	0.7303 (3)	0.0537 (9)
C2	0.59412 (19)	0.2717 (3)	0.6237 (4)	0.0874 (15)
H2	0.6157	0.2919	0.5746	0.105*
C3	0.5398 (2)	0.2438 (4)	0.5888 (4)	0.1010 (17)
H3	0.5250	0.2483	0.5167	0.121*
C4	0.5083 (2)	0.2103 (3)	0.6579 (4)	0.0933 (15)
H4	0.4724	0.1903	0.6335	0.112*
C5	0.5300 (2)	0.2064 (4)	0.7640 (4)	0.1025 (17)
H5	0.5087	0.1839	0.8126	0.123*
C6	0.58346 (19)	0.2358 (3)	0.7998 (4)	0.0836 (14)
H6	0.5978	0.2326	0.8724	0.100*
C7	0.70465 (14)	0.3524 (2)	0.7205 (3)	0.0453 (8)
C8	0.75121 (14)	0.3712 (2)	0.7993 (3)	0.0451 (8)
C9	0.73865 (16)	0.3304 (2)	0.8944 (3)	0.0530 (9)
C10	0.77083 (18)	0.3296 (3)	1.0061 (3)	0.0795 (13)
H10A	0.7491	0.3014	1.0534	0.119*
H10B	0.7793	0.3901	1.0293	0.119*
H10C	0.8046	0.2966	1.0070	0.119*
C11	0.79856 (14)	0.4209 (2)	0.7807 (3)	0.0455 (8)
C12	0.84809 (14)	0.4233 (2)	0.8664 (3)	0.0494 (9)
C13	0.88322 (17)	0.3510 (3)	0.8847 (3)	0.0731 (12)
H13	0.8760	0.2992	0.8438	0.088*
C14	0.9293 (2)	0.3550 (4)	0.9638 (4)	0.0944 (16)
H14	0.9528	0.3057	0.9756	0.113*
C15	0.9408 (2)	0.4301 (4)	1.0244 (4)	0.0952 (16)
H15	0.9719	0.4322	1.0772	0.114*
C16	0.9063 (2)	0.5025 (3)	1.0070 (3)	0.0804 (13)
H16	0.9140	0.5539	1.0484	0.096*
C17	0.86028 (17)	0.5001 (3)	0.9288 (3)	0.0626 (11)
H17	0.8371	0.5499	0.9176	0.075*
C18	0.85002 (14)	0.5064 (2)	0.6746 (3)	0.0484 (9)
C19	0.85793 (16)	0.5962 (3)	0.7029 (3)	0.0603 (10)
H19	0.8312	0.6271	0.7329	0.072*
C20	0.9058 (2)	0.6395 (3)	0.6863 (3)	0.0748 (13)
H20	0.9104	0.7001	0.7032	0.090*
C21	0.94639 (19)	0.5951 (4)	0.6455 (4)	0.0801 (14)
C22	0.93680 (18)	0.5079 (4)	0.6138 (4)	0.0770 (13)
H22	0.9634	0.4783	0.5822	0.092*
C23	0.88931 (16)	0.4620 (3)	0.6266 (3)	0.0600 (10)
C24	1.0014 (2)	0.6409 (4)	0.6354 (4)	0.123 (2)
H24A	0.9956	0.7045	0.6265	0.185*
H24B	1.0153	0.6171	0.5745	0.185*
H24C	1.0278	0.6299	0.6989	0.185*
C25	0.8808 (2)	0.3672 (3)	0.5903 (4)	0.0988 (16)
H25A	0.9061	0.3529	0.5424	0.148*
H25B	0.8435	0.3597	0.5540	0.148*
H25C	0.8872	0.3279	0.6511	0.148*
C26	0.85622 (15)	0.6665 (3)	0.3970 (3)	0.0548 (10)
C27	0.85144 (19)	0.5927 (3)	0.3331 (4)	0.0827 (14)
H27	0.8188	0.5595	0.3231	0.099*
C28	0.8953 (2)	0.5667 (4)	0.2827 (4)	0.1015 (17)
H28	0.8923	0.5154	0.2402	0.122*
C29	0.9428 (2)	0.6162 (5)	0.2953 (4)	0.0951 (17)
H29	0.9718	0.5997	0.2600	0.114*
C30	0.94767 (19)	0.6883 (4)	0.3583 (4)	0.0892 (16)
H30	0.9804	0.7212	0.3676	0.107*
C31	0.90419 (17)	0.7157 (3)	0.4111 (3)	0.0748 (12)
H31	0.9079	0.7663	0.4548	0.090*
C32	0.77607 (13)	0.6380 (2)	0.4921 (3)	0.0446 (8)
C33	0.74543 (13)	0.6953 (2)	0.5496 (3)	0.0431 (8)
C34	0.76731 (14)	0.7834 (2)	0.5365 (3)	0.0515 (9)
C35	0.75288 (18)	0.8717 (3)	0.5797 (4)	0.0743 (12)
H35A	0.7785	0.9166	0.5636	0.112*
H35B	0.7549	0.8674	0.6558	0.112*
H35C	0.7160	0.8882	0.5476	0.112*
C36	0.70392 (13)	0.6653 (2)	0.6090 (2)	0.0405 (8)
C37	0.67006 (13)	0.7349 (2)	0.6529 (3)	0.0424 (8)
C38	0.62550 (16)	0.7727 (3)	0.5871 (3)	0.0647 (11)
H38	0.6167	0.7534	0.5166	0.078*
C39	0.59395 (17)	0.8383 (3)	0.6236 (4)	0.0833 (14)
H39	0.5637	0.8623	0.5786	0.100*
C40	0.60746 (19)	0.8685 (3)	0.7284 (4)	0.0808 (13)
H40	0.5867	0.9135	0.7538	0.097*
C41	0.65155 (18)	0.8313 (3)	0.7936 (3)	0.0681 (11)
H41	0.6605	0.8512	0.8639	0.082*
C42	0.68273 (15)	0.7654 (2)	0.7574 (3)	0.0554 (9)
H42	0.7126	0.7409	0.8031	0.067*
C43	0.65425 (13)	0.5545 (2)	0.6869 (3)	0.0429 (8)
C44	0.66932 (15)	0.5512 (2)	0.7965 (3)	0.0515 (9)
H44	0.7048	0.5691	0.8273	0.062*
C45	0.63270 (17)	0.5219 (2)	0.8614 (3)	0.0610 (10)
H45	0.6437	0.5194	0.9351	0.073*
C46	0.57977 (18)	0.4963 (3)	0.8166 (4)	0.0645 (11)
C47	0.56553 (16)	0.4988 (3)	0.7073 (4)	0.0687 (12)
H47	0.5302	0.4804	0.6767	0.082*
C48	0.60162 (15)	0.5274 (3)	0.6409 (3)	0.0570 (10)
C49	0.5389 (2)	0.4628 (3)	0.8855 (4)	0.0980 (17)
H49A	0.5567	0.4594	0.9586	0.147*
H49B	0.5258	0.4043	0.8615	0.147*
H49C	0.5081	0.5036	0.8799	0.147*
C50	0.58494 (17)	0.5256 (3)	0.5203 (3)	0.0855 (14)
H50A	0.5505	0.4939	0.5020	0.128*
H50B	0.6131	0.4956	0.4888	0.128*
H50C	0.5806	0.5860	0.4936	0.128*
C51	0.7177 (3)	0.4244 (4)	0.3156 (4)	0.154 (3)
H51A	0.7160	0.4890	0.3053	0.185*
H51B	0.6883	0.3962	0.2661	0.185*
C52	0.7725 (4)	0.3881 (6)	0.3038 (8)	0.206 (4)
H52A	0.7799	0.4011	0.2333	0.310*
H52B	0.7729	0.3243	0.3146	0.310*
H52C	0.8005	0.4155	0.3558	0.310*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0507 (3)	0.0407 (3)	0.0398 (3)	−0.0023 (2)	0.0125 (2)	0.00241 (19)
O1	0.0670 (16)	0.0483 (14)	0.0410 (14)	−0.0152 (12)	0.0116 (12)	0.0015 (11)
O2	0.0636 (16)	0.0476 (14)	0.0460 (14)	−0.0051 (12)	0.0213 (12)	0.0012 (11)
O3	0.214 (4)	0.075 (2)	0.0544 (18)	−0.065 (2)	0.063 (2)	−0.0199 (15)
N1	0.066 (2)	0.0477 (17)	0.0431 (18)	−0.0096 (15)	0.0125 (15)	0.0058 (14)
N2	0.070 (2)	0.0549 (19)	0.0502 (19)	−0.0031 (17)	0.0155 (16)	0.0116 (15)
N3	0.0450 (16)	0.0386 (16)	0.0523 (18)	0.0017 (13)	0.0099 (14)	0.0039 (13)
N4	0.0515 (18)	0.0517 (19)	0.0562 (19)	−0.0035 (14)	0.0213 (15)	0.0066 (15)
N5	0.061 (2)	0.0460 (18)	0.069 (2)	−0.0060 (15)	0.0218 (17)	0.0098 (15)
N6	0.0398 (15)	0.0441 (17)	0.0434 (16)	0.0009 (13)	0.0111 (12)	0.0079 (13)
C1	0.065 (2)	0.047 (2)	0.050 (2)	−0.0111 (18)	0.0145 (19)	0.0005 (17)
C2	0.091 (3)	0.108 (4)	0.063 (3)	−0.050 (3)	0.014 (3)	0.000 (3)
C3	0.112 (4)	0.117 (4)	0.071 (3)	−0.052 (3)	0.005 (3)	0.003 (3)
C4	0.077 (3)	0.111 (4)	0.095 (4)	−0.034 (3)	0.020 (3)	−0.010 (3)
C5	0.085 (4)	0.146 (5)	0.083 (4)	−0.046 (3)	0.033 (3)	0.005 (3)
C6	0.081 (3)	0.108 (4)	0.064 (3)	−0.028 (3)	0.021 (2)	0.007 (3)
C7	0.059 (2)	0.0341 (18)	0.046 (2)	−0.0019 (16)	0.0164 (18)	0.0035 (16)
C8	0.052 (2)	0.0387 (19)	0.046 (2)	0.0031 (16)	0.0136 (17)	0.0046 (16)
C9	0.064 (2)	0.049 (2)	0.046 (2)	0.0039 (19)	0.0089 (19)	0.0075 (17)
C10	0.091 (3)	0.096 (3)	0.051 (3)	−0.010 (3)	0.010 (2)	0.023 (2)
C11	0.054 (2)	0.0350 (18)	0.048 (2)	0.0073 (16)	0.0103 (17)	−0.0007 (16)
C12	0.052 (2)	0.049 (2)	0.049 (2)	0.0030 (17)	0.0126 (17)	0.0035 (17)
C13	0.075 (3)	0.060 (3)	0.079 (3)	0.022 (2)	−0.001 (2)	−0.002 (2)
C14	0.076 (3)	0.104 (4)	0.097 (4)	0.032 (3)	−0.008 (3)	0.014 (3)
C15	0.075 (3)	0.125 (5)	0.076 (3)	−0.005 (3)	−0.016 (3)	0.012 (3)
C16	0.100 (4)	0.083 (3)	0.053 (3)	−0.020 (3)	−0.003 (3)	−0.005 (2)
C17	0.078 (3)	0.059 (2)	0.051 (2)	0.008 (2)	0.010 (2)	−0.0014 (19)
C18	0.048 (2)	0.052 (2)	0.045 (2)	−0.0012 (17)	0.0052 (17)	0.0059 (16)
C19	0.071 (3)	0.056 (2)	0.054 (2)	−0.011 (2)	0.010 (2)	−0.0021 (19)
C20	0.096 (3)	0.068 (3)	0.058 (3)	−0.032 (3)	0.007 (2)	0.004 (2)
C21	0.070 (3)	0.108 (4)	0.061 (3)	−0.032 (3)	0.008 (2)	0.016 (3)
C22	0.057 (3)	0.105 (4)	0.072 (3)	0.001 (3)	0.021 (2)	0.006 (3)
C23	0.056 (2)	0.062 (3)	0.065 (3)	0.001 (2)	0.017 (2)	0.000 (2)
C24	0.092 (4)	0.171 (6)	0.105 (4)	−0.066 (4)	0.010 (3)	0.028 (4)
C25	0.088 (3)	0.088 (4)	0.129 (4)	0.005 (3)	0.043 (3)	−0.032 (3)
C26	0.057 (2)	0.064 (2)	0.047 (2)	0.0019 (19)	0.0197 (18)	0.0168 (19)
C27	0.089 (3)	0.094 (4)	0.076 (3)	−0.013 (3)	0.045 (3)	−0.004 (3)
C28	0.117 (4)	0.117 (4)	0.081 (4)	0.003 (4)	0.047 (3)	−0.008 (3)
C29	0.085 (4)	0.129 (5)	0.081 (4)	0.029 (4)	0.042 (3)	0.025 (3)
C30	0.058 (3)	0.129 (5)	0.084 (4)	0.005 (3)	0.023 (3)	0.034 (3)
C31	0.063 (3)	0.090 (3)	0.074 (3)	−0.004 (2)	0.020 (2)	0.017 (2)
C32	0.047 (2)	0.046 (2)	0.041 (2)	−0.0036 (17)	0.0070 (16)	0.0079 (16)
C33	0.043 (2)	0.0428 (19)	0.043 (2)	−0.0020 (15)	0.0068 (16)	0.0052 (15)
C34	0.049 (2)	0.047 (2)	0.060 (2)	−0.0024 (17)	0.0110 (18)	0.0082 (17)
C35	0.079 (3)	0.049 (2)	0.101 (3)	−0.008 (2)	0.032 (3)	0.003 (2)
C36	0.0366 (18)	0.048 (2)	0.0357 (18)	0.0007 (15)	0.0018 (14)	0.0049 (15)
C37	0.0385 (19)	0.045 (2)	0.044 (2)	−0.0006 (15)	0.0073 (16)	0.0034 (16)
C38	0.060 (2)	0.082 (3)	0.050 (2)	0.018 (2)	0.003 (2)	−0.011 (2)
C39	0.062 (3)	0.104 (4)	0.081 (3)	0.034 (3)	0.001 (2)	−0.009 (3)
C40	0.077 (3)	0.086 (3)	0.081 (3)	0.027 (3)	0.016 (3)	−0.017 (3)
C41	0.087 (3)	0.068 (3)	0.050 (2)	0.010 (2)	0.013 (2)	−0.008 (2)
C42	0.062 (2)	0.052 (2)	0.050 (2)	0.0044 (19)	0.0016 (18)	−0.0004 (18)
C43	0.0408 (19)	0.0391 (18)	0.051 (2)	0.0010 (15)	0.0152 (17)	0.0038 (15)
C44	0.051 (2)	0.053 (2)	0.053 (2)	−0.0068 (17)	0.0150 (18)	0.0021 (17)
C45	0.078 (3)	0.057 (2)	0.055 (2)	−0.007 (2)	0.030 (2)	0.0021 (19)
C46	0.070 (3)	0.059 (2)	0.076 (3)	−0.012 (2)	0.043 (2)	−0.004 (2)
C47	0.048 (2)	0.078 (3)	0.084 (3)	−0.019 (2)	0.023 (2)	−0.008 (2)
C48	0.048 (2)	0.064 (3)	0.060 (2)	−0.0049 (19)	0.0131 (19)	0.003 (2)
C49	0.110 (4)	0.095 (4)	0.106 (4)	−0.030 (3)	0.068 (3)	−0.005 (3)
C50	0.058 (3)	0.123 (4)	0.073 (3)	−0.018 (3)	0.004 (2)	0.001 (3)
C51	0.202 (6)	0.099 (5)	0.166 (6)	−0.072 (5)	0.045 (5)	−0.026 (4)
C52	0.278 (8)	0.151 (6)	0.204 (7)	−0.040 (6)	0.081 (7)	−0.025 (6)

Geometric parameters (Å, º)

Ni1—O1	1.982 (2)	C23—C25	1.488 (6)
Ni1—O2	1.967 (2)	C24—H24A	0.9600
Ni1—O3	2.094 (3)	C24—H24B	0.9600
Ni1—N3	2.020 (3)	C24—H24C	0.9600
Ni1—N6	2.025 (3)	C25—H25A	0.9600
O1—C7	1.275 (4)	C25—H25B	0.9600
O2—C32	1.272 (4)	C25—H25C	0.9600
O3—C51	1.475 (4)	C26—C27	1.358 (6)
O3—H3O	0.8500	C26—C31	1.371 (5)
N1—C7	1.368 (4)	C27—C28	1.391 (6)
N1—N2	1.404 (4)	C27—H27	0.9300
N1—C1	1.411 (4)	C28—C29	1.364 (7)
N2—C9	1.314 (4)	C28—H28	0.9300
N3—C11	1.312 (4)	C29—C30	1.332 (7)
N3—C18	1.440 (4)	C29—H29	0.9300
N4—C32	1.366 (4)	C30—C31	1.407 (6)
N4—N5	1.398 (4)	C30—H30	0.9300
N4—C26	1.412 (4)	C31—H31	0.9300
N5—C34	1.308 (4)	C32—C33	1.415 (4)
N6—C36	1.317 (4)	C33—C36	1.431 (4)
N6—C43	1.434 (4)	C33—C34	1.436 (4)
C1—C2	1.368 (5)	C34—C35	1.488 (5)
C1—C6	1.371 (5)	C35—H35A	0.9600
C2—C3	1.395 (6)	C35—H35B	0.9600
C2—H2	0.9300	C35—H35C	0.9600
C3—C4	1.353 (6)	C36—C37	1.490 (4)
C3—H3	0.9300	C37—C38	1.381 (5)
C4—C5	1.365 (6)	C37—C42	1.387 (5)
C4—H4	0.9300	C38—C39	1.370 (5)
C5—C6	1.385 (6)	C38—H38	0.9300
C5—H5	0.9300	C39—C40	1.391 (6)
C6—H6	0.9300	C39—H39	0.9300
C7—C8	1.416 (5)	C40—C41	1.365 (5)
C8—C9	1.426 (5)	C40—H40	0.9300
C8—C11	1.426 (5)	C41—C42	1.368 (5)
C9—C10	1.505 (5)	C41—H41	0.9300
C10—H10A	0.9600	C42—H42	0.9300
C10—H10B	0.9600	C43—C44	1.379 (5)
C10—H10C	0.9600	C43—C48	1.385 (5)
C11—C12	1.490 (5)	C44—C45	1.382 (5)
C12—C13	1.373 (5)	C44—H44	0.9300
C12—C17	1.394 (5)	C45—C46	1.381 (6)
C13—C14	1.384 (6)	C45—H45	0.9300
C13—H13	0.9300	C46—C47	1.374 (6)
C14—C15	1.359 (7)	C46—C49	1.515 (5)
C14—H14	0.9300	C47—C48	1.383 (5)
C15—C16	1.364 (7)	C47—H47	0.9300
C15—H15	0.9300	C48—C50	1.517 (5)
C16—C17	1.374 (6)	C49—H49A	0.9600
C16—H16	0.9300	C49—H49B	0.9600
C17—H17	0.9300	C49—H49C	0.9600
C18—C23	1.386 (5)	C50—H50A	0.9600
C18—C19	1.390 (5)	C50—H50B	0.9600
C19—C20	1.382 (5)	C50—H50C	0.9600
C19—H19	0.9300	C51—C52	1.478 (5)
C20—C21	1.363 (6)	C51—H51A	0.9700
C20—H20	0.9300	C51—H51B	0.9700
C21—C22	1.367 (6)	C52—H52A	0.9600
C21—C24	1.534 (6)	C52—H52B	0.9600
C22—C23	1.381 (6)	C52—H52C	0.9600
C22—H22	0.9300
O1—Ni1—O2	163.8 (1)	H24A—C24—H24C	109.5
O1—Ni1—O3	80.1 (1)	H24B—C24—H24C	109.5
O1—Ni1—N3	92.4 (1)	C23—C25—H25A	109.5
O1—Ni1—N6	98.8 (1)	C23—C25—H25B	109.5
O2—Ni1—O3	83.7 (1)	H25A—C25—H25B	109.5
O2—Ni1—N3	97.3 (1)	C23—C25—H25C	109.5
O2—Ni1—N6	92.4 (1)	H25A—C25—H25C	109.5
O3—Ni1—N3	130.8 (1)	H25B—C25—H25C	109.5
O3—Ni1—N6	129.0 (1)	C27—C26—C31	119.9 (4)
N3—Ni1—N6	100.1 (1)	C27—C26—N4	120.1 (4)
C7—O1—Ni1	120.3 (2)	C31—C26—N4	119.9 (4)
C32—O2—Ni1	121.8 (2)	C26—C27—C28	120.0 (5)
C51—O3—Ni1	130.0 (3)	C26—C27—H27	120.0
C51—O3—H3O	115.0	C28—C27—H27	120.0
Ni1—O3—H3O	115.0	C29—C28—C27	120.2 (5)
C7—N1—N2	110.8 (3)	C29—C28—H28	119.9
C7—N1—C1	130.5 (3)	C27—C28—H28	119.9
N2—N1—C1	118.2 (3)	C30—C29—C28	119.7 (5)
C9—N2—N1	105.8 (3)	C30—C29—H29	120.1
C11—N3—C18	118.0 (3)	C28—C29—H29	120.1
C11—N3—Ni1	126.4 (2)	C29—C30—C31	121.3 (5)
C18—N3—Ni1	115.6 (2)	C29—C30—H30	119.4
C32—N4—N5	111.6 (3)	C31—C30—H30	119.4
C32—N4—C26	128.4 (3)	C26—C31—C30	118.8 (5)
N5—N4—C26	119.3 (3)	C26—C31—H31	120.6
C34—N5—N4	105.8 (3)	C30—C31—H31	120.6
C36—N6—C43	117.9 (3)	O2—C32—N4	123.6 (3)
C36—N6—Ni1	126.9 (2)	O2—C32—C33	130.3 (3)
C43—N6—Ni1	115.0 (2)	N4—C32—C33	106.1 (3)
C2—C1—C6	118.3 (4)	C32—C33—C36	124.4 (3)
C2—C1—N1	121.5 (3)	C32—C33—C34	104.6 (3)
C6—C1—N1	120.1 (4)	C36—C33—C34	131.0 (3)
C1—C2—C3	120.0 (4)	N5—C34—C33	111.9 (3)
C1—C2—H2	120.0	N5—C34—C35	117.6 (3)
C3—C2—H2	120.0	C33—C34—C35	130.4 (3)
C4—C3—C2	121.3 (5)	C34—C35—H35A	109.5
C4—C3—H3	119.4	C34—C35—H35B	109.5
C2—C3—H3	119.4	H35A—C35—H35B	109.5
C3—C4—C5	118.8 (5)	C34—C35—H35C	109.5
C3—C4—H4	120.6	H35A—C35—H35C	109.5
C5—C4—H4	120.6	H35B—C35—H35C	109.5
C4—C5—C6	120.4 (4)	N6—C36—C33	121.3 (3)
C4—C5—H5	119.8	N6—C36—C37	120.9 (3)
C6—C5—H5	119.8	C33—C36—C37	117.7 (3)
C1—C6—C5	121.1 (4)	C38—C37—C42	118.4 (3)
C1—C6—H6	119.4	C38—C37—C36	119.4 (3)
C5—C6—H6	119.4	C42—C37—C36	122.2 (3)
O1—C7—N1	123.1 (3)	C39—C38—C37	121.3 (4)
O1—C7—C8	130.2 (3)	C39—C38—H38	119.4
N1—C7—C8	106.6 (3)	C37—C38—H38	119.4
C7—C8—C9	104.6 (3)	C38—C39—C40	119.6 (4)
C7—C8—C11	124.6 (3)	C38—C39—H39	120.2
C9—C8—C11	130.8 (3)	C40—C39—H39	120.2
N2—C9—C8	112.1 (3)	C41—C40—C39	119.3 (4)
N2—C9—C10	117.6 (3)	C41—C40—H40	120.4
C8—C9—C10	130.3 (4)	C39—C40—H40	120.4
C9—C10—H10A	109.5	C40—C41—C42	121.1 (4)
C9—C10—H10B	109.5	C40—C41—H41	119.5
H10A—C10—H10B	109.5	C42—C41—H41	119.5
C9—C10—H10C	109.5	C41—C42—C37	120.4 (3)
H10A—C10—H10C	109.5	C41—C42—H42	119.8
H10B—C10—H10C	109.5	C37—C42—H42	119.8
N3—C11—C8	121.3 (3)	C44—C43—C48	119.4 (3)
N3—C11—C12	120.1 (3)	C44—C43—N6	119.6 (3)
C8—C11—C12	118.6 (3)	C48—C43—N6	120.8 (3)
C13—C12—C17	118.4 (4)	C43—C44—C45	121.2 (3)
C13—C12—C11	121.1 (3)	C43—C44—H44	119.4
C17—C12—C11	120.5 (3)	C45—C44—H44	119.4
C12—C13—C14	120.2 (4)	C46—C45—C44	119.9 (4)
C12—C13—H13	119.9	C46—C45—H45	120.0
C14—C13—H13	119.9	C44—C45—H45	120.0
C15—C14—C13	120.9 (5)	C47—C46—C45	118.3 (4)
C15—C14—H14	119.5	C47—C46—C49	120.5 (4)
C13—C14—H14	119.5	C45—C46—C49	121.2 (4)
C14—C15—C16	119.5 (5)	C46—C47—C48	122.7 (4)
C14—C15—H15	120.2	C46—C47—H47	118.7
C16—C15—H15	120.2	C48—C47—H47	118.7
C15—C16—C17	120.6 (4)	C47—C48—C43	118.4 (4)
C15—C16—H16	119.7	C47—C48—C50	120.9 (4)
C17—C16—H16	119.7	C43—C48—C50	120.6 (3)
C16—C17—C12	120.4 (4)	C46—C49—H49A	109.5
C16—C17—H17	119.8	C46—C49—H49B	109.5
C12—C17—H17	119.8	H49A—C49—H49B	109.5
C23—C18—C19	119.7 (3)	C46—C49—H49C	109.5
C23—C18—N3	121.1 (3)	H49A—C49—H49C	109.5
C19—C18—N3	119.1 (3)	H49B—C49—H49C	109.5
C20—C19—C18	119.6 (4)	C48—C50—H50A	109.5
C20—C19—H19	120.2	C48—C50—H50B	109.5
C18—C19—H19	120.2	H50A—C50—H50B	109.5
C21—C20—C19	121.4 (4)	C48—C50—H50C	109.5
C21—C20—H20	119.3	H50A—C50—H50C	109.5
C19—C20—H20	119.3	H50B—C50—H50C	109.5
C20—C21—C22	118.1 (4)	O3—C51—C52	101.1 (6)
C20—C21—C24	121.4 (5)	O3—C51—H51A	111.5
C22—C21—C24	120.6 (5)	C52—C51—H51A	111.5
C21—C22—C23	122.9 (4)	O3—C51—H51B	111.5
C21—C22—H22	118.6	C52—C51—H51B	111.5
C23—C22—H22	118.6	H51A—C51—H51B	109.4
C22—C23—C18	118.2 (4)	C51—C52—H52A	109.5
C22—C23—C25	120.8 (4)	C51—C52—H52B	109.5
C18—C23—C25	121.0 (4)	H52A—C52—H52B	109.5
C21—C24—H24A	109.5	C51—C52—H52C	109.5
C21—C24—H24B	109.5	H52A—C52—H52C	109.5
H24A—C24—H24B	109.5	H52B—C52—H52C	109.5
C21—C24—H24C	109.5
O2—Ni1—O1—C7	149.2 (3)	C11—N3—C18—C19	−91.6 (4)
N3—Ni1—O1—C7	22.6 (3)	Ni1—N3—C18—C19	87.0 (3)
N6—Ni1—O1—C7	−78.0 (3)	C23—C18—C19—C20	−2.2 (5)
O3—Ni1—O1—C7	153.7 (3)	N3—C18—C19—C20	−178.5 (3)
O1—Ni1—O2—C32	151.9 (3)	C18—C19—C20—C21	−2.1 (6)
N3—Ni1—O2—C32	−82.1 (3)	C19—C20—C21—C22	4.9 (7)
N6—Ni1—O2—C32	18.4 (3)	C19—C20—C21—C24	−175.1 (4)
O3—Ni1—O2—C32	147.4 (3)	C20—C21—C22—C23	−3.6 (7)
O2—Ni1—O3—C51	−14.3 (5)	C24—C21—C22—C23	176.3 (4)
O1—Ni1—O3—C51	166.9 (5)	C21—C22—C23—C18	−0.5 (7)
N3—Ni1—O3—C51	−108.5 (5)	C21—C22—C23—C25	179.8 (5)
N6—Ni1—O3—C51	73.6 (5)	C19—C18—C23—C22	3.4 (6)
C7—N1—N2—C9	−1.3 (4)	N3—C18—C23—C22	179.6 (3)
C1—N1—N2—C9	−174.1 (3)	C19—C18—C23—C25	−176.9 (4)
O2—Ni1—N3—C11	175.3 (3)	N3—C18—C23—C25	−0.6 (6)
O1—Ni1—N3—C11	−17.8 (3)	C32—N4—C26—C27	35.5 (6)
N6—Ni1—N3—C11	81.6 (3)	N5—N4—C26—C27	−155.0 (4)
O3—Ni1—N3—C11	−96.7 (3)	C32—N4—C26—C31	−143.8 (4)
O2—Ni1—N3—C18	−3.1 (2)	N5—N4—C26—C31	25.8 (5)
O1—Ni1—N3—C18	163.8 (2)	C31—C26—C27—C28	0.5 (7)
N6—Ni1—N3—C18	−96.8 (2)	N4—C26—C27—C28	−178.8 (4)
O3—Ni1—N3—C18	84.8 (3)	C26—C27—C28—C29	−1.4 (8)
C32—N4—N5—C34	−1.7 (4)	C27—C28—C29—C30	1.8 (8)
C26—N4—N5—C34	−173.0 (3)	C28—C29—C30—C31	−1.2 (8)
O2—Ni1—N6—C36	−11.8 (3)	C27—C26—C31—C30	0.1 (6)
O1—Ni1—N6—C36	−179.9 (3)	N4—C26—C31—C30	179.4 (3)
N3—Ni1—N6—C36	86.1 (3)	C29—C30—C31—C26	0.2 (7)
O3—Ni1—N6—C36	−95.5 (3)	Ni1—O2—C32—N4	163.4 (2)
O2—Ni1—N6—C43	173.3 (2)	Ni1—O2—C32—C33	−18.0 (5)
O1—Ni1—N6—C43	5.2 (2)	N5—N4—C32—O2	−179.9 (3)
N3—Ni1—N6—C43	−88.8 (2)	C26—N4—C32—O2	−9.6 (6)
O3—Ni1—N6—C43	89.6 (2)	N5—N4—C32—C33	1.3 (4)
C7—N1—C1—C2	14.8 (6)	C26—N4—C32—C33	171.5 (3)
N2—N1—C1—C2	−174.0 (4)	O2—C32—C33—C36	3.0 (6)
C7—N1—C1—C6	−165.2 (4)	N4—C32—C33—C36	−178.2 (3)
N2—N1—C1—C6	5.9 (5)	O2—C32—C33—C34	−179.1 (3)
C6—C1—C2—C3	2.7 (7)	N4—C32—C33—C34	−0.3 (3)
N1—C1—C2—C3	−177.3 (4)	N4—N5—C34—C33	1.5 (4)
C1—C2—C3—C4	−3.1 (8)	N4—N5—C34—C35	179.7 (3)
C2—C3—C4—C5	1.8 (9)	C32—C33—C34—N5	−0.8 (4)
C3—C4—C5—C6	−0.4 (9)	C36—C33—C34—N5	176.9 (3)
C2—C1—C6—C5	−1.4 (7)	C32—C33—C34—C35	−178.7 (4)
N1—C1—C6—C5	178.7 (4)	C36—C33—C34—C35	−1.1 (6)
C4—C5—C6—C1	0.2 (8)	C43—N6—C36—C33	176.8 (3)
Ni1—O1—C7—N1	163.2 (2)	Ni1—N6—C36—C33	2.1 (4)
Ni1—O1—C7—C8	−18.3 (5)	C43—N6—C36—C37	−5.5 (4)
N2—N1—C7—O1	−178.8 (3)	Ni1—N6—C36—C37	179.7 (2)
C1—N1—C7—O1	−7.1 (6)	C32—C33—C36—N6	5.9 (5)
N2—N1—C7—C8	2.4 (4)	C34—C33—C36—N6	−171.3 (3)
C1—N1—C7—C8	174.1 (3)	C32—C33—C36—C37	−171.8 (3)
O1—C7—C8—C9	178.9 (3)	C34—C33—C36—C37	10.9 (5)
N1—C7—C8—C9	−2.5 (4)	N6—C36—C37—C38	−96.3 (4)
O1—C7—C8—C11	−1.1 (6)	C33—C36—C37—C38	81.4 (4)
N1—C7—C8—C11	177.6 (3)	N6—C36—C37—C42	85.7 (4)
N1—N2—C9—C8	−0.3 (4)	C33—C36—C37—C42	−96.6 (4)
N1—N2—C9—C10	179.2 (3)	C42—C37—C38—C39	−0.6 (6)
C7—C8—C9—N2	1.8 (4)	C36—C37—C38—C39	−178.7 (4)
C11—C8—C9—N2	−178.3 (3)	C37—C38—C39—C40	1.1 (7)
C7—C8—C9—C10	−177.7 (4)	C38—C39—C40—C41	−0.9 (7)
C11—C8—C9—C10	2.2 (6)	C39—C40—C41—C42	0.4 (7)
C18—N3—C11—C8	−176.0 (3)	C40—C41—C42—C37	0.1 (6)
Ni1—N3—C11—C8	5.5 (4)	C38—C37—C42—C41	0.0 (5)
C18—N3—C11—C12	2.8 (4)	C36—C37—C42—C41	178.0 (3)
Ni1—N3—C11—C12	−175.6 (2)	C36—N6—C43—C44	−82.7 (4)
C7—C8—C11—N3	8.4 (5)	Ni1—N6—C43—C44	92.7 (3)
C9—C8—C11—N3	−171.5 (3)	C36—N6—C43—C48	102.3 (4)
C7—C8—C11—C12	−170.5 (3)	Ni1—N6—C43—C48	−82.3 (3)
C9—C8—C11—C12	9.6 (5)	C48—C43—C44—C45	−0.4 (5)
N3—C11—C12—C13	−102.6 (4)	N6—C43—C44—C45	−175.5 (3)
C8—C11—C12—C13	76.3 (4)	C43—C44—C45—C46	−0.8 (6)
N3—C11—C12—C17	76.4 (4)	C44—C45—C46—C47	1.6 (6)
C8—C11—C12—C17	−104.7 (4)	C44—C45—C46—C49	179.3 (4)
C17—C12—C13—C14	0.2 (6)	C45—C46—C47—C48	−1.3 (6)
C11—C12—C13—C14	179.2 (4)	C49—C46—C47—C48	−179.0 (4)
C12—C13—C14—C15	−0.1 (8)	C46—C47—C48—C43	0.1 (6)
C13—C14—C15—C16	0.1 (8)	C46—C47—C48—C50	177.5 (4)
C14—C15—C16—C17	−0.1 (8)	C44—C43—C48—C47	0.8 (5)
C15—C16—C17—C12	0.2 (7)	N6—C43—C48—C47	175.8 (3)
C13—C12—C17—C16	−0.3 (6)	C44—C43—C48—C50	−176.7 (4)
C11—C12—C17—C16	−179.3 (4)	N6—C43—C48—C50	−1.7 (5)
C11—N3—C18—C23	92.1 (4)	Ni1—O3—C51—C52	94.4 (6)
Ni1—N3—C18—C23	−89.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N2^i	0.85	2.15	2.910 (4)	148

Symmetry code: (i) x, −y+1/2, z−1/2.