meso-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra­azacyclo­tetra­deca-1,7-diene)nickel(II) bis­[dioxalato(1,10-phenanthroline)chromate(III)] octa­hydrate

Wang, W.-B.; Yang, L.-X.; Lin, Y.

doi:10.1107/S1600536807007209

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meso-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-1,7-diene)nickel(II) bis[dioxalato(1,10-phenanthroline)chromate(III)] octahydrate

W.-B. Wang, L.-X. Yang and Y. Lin

The asymmetric unit of the title complex, [meso-Ni(1,7-CT)][Cr(C₂O₄)₂(phen)]₂·8H₂O (1,7-CT is 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradeca-1,7-diene; phen is 1,10-phenanthroline) or [Ni(C₁₆H₃₂N₄)][Cr(C₂O₄)₂(C₁₂H₈N₂)]₂·8H₂O, consists of one-half of an [Ni(1,7-CT)]²⁺ cation, one [Cr(C₂O₄)₂(phen)]⁻ anion and four water molecules of crystallization. The Ni^II atom (site symmetry $\overline{1}$ ) is coordinated by four N atoms from the tetraazamacrocycle in a square-planar geometry, while the Cr^III centre has a distorted cis-CrN₂O₄ octahedral geometry. A network of π–π stacking interactions and O—H

O and N—H

O hydrogen bonds helps the formation of a three-dimensional structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007209/hb2286sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007209/hb2286Isup2.hkl Contains datablock I

CCDC reference: 633778

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
H-atom completeness 97%
R factor = 0.037
wR factor = 0.100
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C13    -   C14    ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C15    -   C16    ...       1.55 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C48 H64 Cr2 N8 Ni1 O24
            Atom count from the _atom_site data:  C48 H62 Cr2 N8 Ni1 O24
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    1
           From the CIF: _chemical_formula_sum  C48 H64 Cr2 N8 Ni O24
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         48.00     48.00    0.00
           H         64.00     62.00    2.00
           Cr         2.00      2.00    0.00
           N          8.00      8.00    0.00
           Ni         1.00      1.00    0.00
           O         24.00     24.00    0.00

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

Computing details top

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: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

meso-(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca- 1,7-diene)nickel(II) bis[dioxalato(1,10-phenanthroline)chromate(III)] octahydrate top

Crystal data top

[Ni(C₁₆H₃₂N₄)][Cr(C₂O₄)₂(C₁₂H₈N₂)]₂·8H₂O	Z = 1
M_r = 1299.78	F(000) = 676
Triclinic, P1	D_x = 1.561 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8465 (8) Å	Cell parameters from 4761 reflections
b = 11.5280 (9) Å	θ = 2.5–29.5°
c = 12.8997 (10) Å	µ = 0.81 mm⁻¹
α = 77.683 (1)°	T = 273 K
β = 80.891 (1)°	Block, red
γ = 76.669 (1)°	0.38 × 0.34 × 0.21 mm
V = 1382.80 (19) Å³

Data collection top

Bruker SMART APEX-II CCD diffractometer	5064 independent reflections
Radiation source: fine-focus sealed tube	4518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
T_min = 0.747, T_max = 0.848	k = −7→13
7629 measured reflections	l = −14→15

Refinement top

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)] = 0.037	Hydrogen site location: difmap and geom
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0438P)² + 1.3721P] where P = (F_o² + 2F_c²)/3
5064 reflections	(Δ/σ)_max < 0.001
407 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cr1	0.34916 (4)	0.81622 (3)	0.80274 (3)	0.03093 (12)
Ni1	1.0000	0.5000	0.5000	0.03274 (13)
N1	0.3969 (2)	0.96824 (18)	0.83740 (16)	0.0322 (4)
N2	0.2343 (2)	0.82025 (18)	0.95112 (16)	0.0330 (4)
N3	0.8119 (2)	0.5266 (2)	0.4651 (2)	0.0475 (6)
H4	0.7813	0.4849	0.5285	0.057*
N4	1.0361 (2)	0.36203 (19)	0.43248 (17)	0.0364 (5)
O1	0.31191 (19)	0.65896 (16)	0.79521 (15)	0.0408 (4)
O2	0.52589 (19)	0.71570 (16)	0.85097 (15)	0.0404 (4)
O3	0.17833 (18)	0.91083 (17)	0.74177 (14)	0.0387 (4)
O4	0.43167 (18)	0.84710 (17)	0.65425 (14)	0.0404 (4)
O5	0.4138 (3)	0.46281 (19)	0.8159 (2)	0.0642 (6)
O6	0.6552 (2)	0.5292 (2)	0.8499 (2)	0.0746 (8)
O7	0.3706 (2)	0.9176 (2)	0.48976 (15)	0.0542 (5)
O8	0.1016 (2)	1.0046 (2)	0.58619 (17)	0.0594 (6)
O1W	0.1806 (3)	0.8691 (2)	0.3646 (2)	0.0595 (6)
O2W	0.1425 (3)	0.4171 (3)	0.8973 (3)	0.0791 (8)
O3W	0.2565 (4)	0.6250 (3)	0.3288 (3)	0.0975 (11)
O4W	0.8992 (4)	0.5927 (3)	0.8816 (3)	0.0816 (8)
C1	0.4866 (3)	1.0361 (2)	0.7830 (2)	0.0398 (6)
H1	0.5377	1.0153	0.7202	0.048*
C2	0.5066 (3)	1.1372 (3)	0.8170 (2)	0.0447 (7)
H2	0.5718	1.1814	0.7779	0.054*
C3	0.4306 (3)	1.1715 (2)	0.9076 (2)	0.0425 (6)
H3	0.4422	1.2400	0.9295	0.051*
C4	0.3346 (3)	1.1023 (2)	0.9673 (2)	0.0343 (5)
C5	0.2485 (3)	1.1299 (2)	1.0629 (2)	0.0424 (6)
H5	0.2547	1.1978	1.0885	0.051*
C6	0.1588 (3)	1.0595 (3)	1.1165 (2)	0.0424 (6)
H6	0.1020	1.0811	1.1770	0.051*
C7	0.1493 (3)	0.9518 (2)	1.08167 (19)	0.0347 (5)
C8	0.0609 (3)	0.8725 (3)	1.1350 (2)	0.0441 (6)
H8	0.0023	0.8891	1.1963	0.053*
C9	0.0615 (3)	0.7715 (3)	1.0965 (2)	0.0495 (7)
H9	0.0032	0.7187	1.1314	0.059*
C10	0.1501 (3)	0.7472 (3)	1.0042 (2)	0.0443 (6)
H10	0.1499	0.6773	0.9792	0.053*
C11	0.2333 (2)	0.9220 (2)	0.98917 (19)	0.0301 (5)
C12	0.3236 (2)	0.9996 (2)	0.92974 (19)	0.0295 (5)
C13	0.5456 (3)	0.6040 (3)	0.8415 (2)	0.0439 (6)
C14	0.4146 (3)	0.5687 (2)	0.8156 (2)	0.0416 (6)
C15	0.3438 (3)	0.9007 (2)	0.5864 (2)	0.0370 (6)
C16	0.1926 (3)	0.9442 (2)	0.6397 (2)	0.0369 (6)
C17	0.9077 (3)	0.3416 (3)	0.4005 (3)	0.0521 (7)
H17A	0.8659	0.2850	0.4562	0.062*
H17B	0.9295	0.3082	0.3355	0.062*
C18	0.8098 (4)	0.4601 (4)	0.3829 (4)	0.0786 (13)
H18A	0.8367	0.5063	0.3136	0.094*
H18B	0.7154	0.4478	0.3837	0.094*
C19	0.7243 (3)	0.6532 (2)	0.4502 (2)	0.0447 (7)
C20	0.7912 (4)	0.7358 (3)	0.3593 (3)	0.0703 (10)
H20A	0.8879	0.7282	0.3683	0.105*
H20B	0.7426	0.8183	0.3590	0.105*
H20C	0.7855	0.7135	0.2927	0.105*
C21	0.5754 (3)	0.6512 (3)	0.4302 (4)	0.0676 (10)
H21A	0.5797	0.6219	0.3653	0.101*
H21B	0.5191	0.7318	0.4242	0.101*
H21C	0.5343	0.5988	0.4888	0.101*
C22	0.7155 (3)	0.6938 (3)	0.5556 (3)	0.0616 (9)
H22A	0.6499	0.7711	0.5525	0.074*
H22B	0.6753	0.6360	0.6110	0.074*
C23	1.1535 (3)	0.2922 (2)	0.4103 (2)	0.0411 (6)
C24	1.1705 (4)	0.1919 (3)	0.3491 (3)	0.0590 (9)
H24A	1.1335	0.1257	0.3939	0.089*
H24B	1.2684	0.1646	0.3268	0.089*
H24C	1.1205	0.2212	0.2874	0.089*
H1A	0.094 (4)	0.911 (3)	0.382 (3)	0.066 (11)*
H1B	0.225 (4)	0.893 (4)	0.410 (3)	0.079 (13)*
H2A	0.233 (12)	0.431 (11)	0.885 (10)	0.34 (6)*
H3A	0.224 (6)	0.706 (5)	0.318 (4)	0.121 (19)*
H3B	0.289 (6)	0.620 (5)	0.260 (5)	0.114 (18)*
H4A	0.977 (7)	0.531 (6)	0.881 (5)	0.15 (2)*
H4B	0.870 (5)	0.569 (4)	0.953 (4)	0.091 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0298 (2)	0.0320 (2)	0.0323 (2)	−0.00480 (16)	−0.00061 (15)	−0.01271 (16)
Ni1	0.0316 (2)	0.0284 (2)	0.0398 (3)	−0.00273 (18)	0.00047 (18)	−0.01656 (19)
N1	0.0312 (10)	0.0314 (10)	0.0332 (11)	−0.0065 (8)	−0.0003 (8)	−0.0064 (8)
N2	0.0364 (11)	0.0335 (11)	0.0319 (10)	−0.0119 (9)	−0.0010 (8)	−0.0090 (8)
N3	0.0390 (12)	0.0386 (13)	0.0701 (16)	0.0008 (10)	−0.0119 (11)	−0.0263 (12)
N4	0.0423 (12)	0.0312 (11)	0.0366 (11)	−0.0044 (9)	−0.0009 (9)	−0.0142 (9)
O1	0.0394 (10)	0.0387 (10)	0.0504 (11)	−0.0081 (8)	−0.0076 (8)	−0.0197 (8)
O2	0.0378 (10)	0.0378 (10)	0.0489 (11)	−0.0060 (8)	−0.0115 (8)	−0.0123 (8)
O3	0.0301 (9)	0.0464 (10)	0.0373 (10)	−0.0011 (8)	0.0013 (7)	−0.0135 (8)
O4	0.0323 (9)	0.0506 (11)	0.0345 (9)	0.0010 (8)	0.0018 (7)	−0.0140 (8)
O5	0.0681 (15)	0.0362 (11)	0.0954 (18)	−0.0100 (10)	−0.0195 (13)	−0.0206 (11)
O6	0.0506 (13)	0.0516 (14)	0.124 (2)	0.0082 (11)	−0.0290 (14)	−0.0274 (14)
O7	0.0552 (12)	0.0712 (14)	0.0334 (11)	−0.0060 (11)	0.0007 (9)	−0.0152 (9)
O8	0.0443 (12)	0.0758 (16)	0.0514 (13)	0.0033 (11)	−0.0140 (10)	−0.0076 (11)
O1W	0.0633 (15)	0.0588 (14)	0.0587 (14)	−0.0021 (12)	−0.0095 (12)	−0.0248 (11)
O2W	0.0714 (18)	0.0783 (18)	0.092 (2)	−0.0235 (15)	−0.0120 (15)	−0.0145 (15)
O3W	0.149 (3)	0.0566 (18)	0.072 (2)	−0.0126 (19)	0.012 (2)	−0.0044 (15)
O4W	0.0739 (19)	0.0757 (19)	0.095 (2)	−0.0066 (16)	−0.0192 (17)	−0.0184 (17)
C1	0.0345 (13)	0.0406 (14)	0.0414 (14)	−0.0099 (11)	0.0032 (11)	−0.0041 (11)
C2	0.0418 (15)	0.0392 (15)	0.0532 (17)	−0.0176 (12)	−0.0041 (13)	0.0006 (12)
C3	0.0472 (15)	0.0298 (13)	0.0543 (17)	−0.0121 (11)	−0.0136 (13)	−0.0058 (12)
C4	0.0371 (13)	0.0278 (12)	0.0396 (13)	−0.0038 (10)	−0.0106 (11)	−0.0081 (10)
C5	0.0517 (16)	0.0348 (14)	0.0451 (15)	−0.0043 (12)	−0.0093 (12)	−0.0188 (12)
C6	0.0468 (15)	0.0465 (15)	0.0363 (14)	−0.0043 (12)	−0.0023 (12)	−0.0204 (12)
C7	0.0338 (13)	0.0412 (14)	0.0301 (12)	−0.0067 (11)	−0.0028 (10)	−0.0105 (10)
C8	0.0422 (15)	0.0583 (18)	0.0327 (13)	−0.0156 (13)	0.0048 (11)	−0.0111 (12)
C9	0.0514 (17)	0.0590 (18)	0.0431 (16)	−0.0301 (15)	0.0073 (13)	−0.0090 (13)
C10	0.0519 (16)	0.0425 (15)	0.0439 (15)	−0.0225 (13)	0.0035 (12)	−0.0125 (12)
C11	0.0308 (12)	0.0316 (12)	0.0298 (12)	−0.0065 (10)	−0.0043 (9)	−0.0087 (9)
C12	0.0289 (12)	0.0286 (12)	0.0312 (12)	−0.0037 (9)	−0.0050 (9)	−0.0072 (9)
C13	0.0414 (15)	0.0383 (15)	0.0519 (16)	−0.0030 (12)	−0.0077 (12)	−0.0118 (12)
C14	0.0448 (15)	0.0372 (15)	0.0455 (15)	−0.0068 (12)	−0.0033 (12)	−0.0165 (12)
C15	0.0388 (14)	0.0376 (14)	0.0361 (14)	−0.0056 (11)	−0.0007 (11)	−0.0153 (11)
C16	0.0337 (13)	0.0378 (14)	0.0414 (14)	−0.0046 (11)	−0.0053 (11)	−0.0142 (11)
C17	0.0558 (18)	0.0436 (16)	0.066 (2)	−0.0050 (14)	−0.0150 (15)	−0.0292 (14)
C18	0.072 (2)	0.074 (2)	0.104 (3)	0.0181 (19)	−0.044 (2)	−0.057 (2)
C19	0.0355 (14)	0.0374 (14)	0.0620 (18)	−0.0016 (11)	−0.0062 (13)	−0.0169 (13)
C20	0.081 (3)	0.066 (2)	0.068 (2)	−0.029 (2)	−0.031 (2)	0.0096 (18)
C21	0.0389 (17)	0.056 (2)	0.111 (3)	0.0028 (15)	−0.0148 (18)	−0.031 (2)
C22	0.0408 (16)	0.069 (2)	0.075 (2)	0.0039 (15)	0.0052 (15)	−0.0394 (18)
C23	0.0503 (16)	0.0336 (13)	0.0352 (13)	0.0000 (12)	0.0044 (12)	−0.0128 (11)
C24	0.078 (2)	0.0416 (16)	0.0539 (18)	0.0078 (15)	−0.0028 (16)	−0.0261 (14)

Geometric parameters (Å, º) top

Cr1—O4	1.9507 (18)	C3—H3	0.9300
Cr1—O1	1.9554 (18)	C4—C12	1.403 (3)
Cr1—O3	1.9608 (18)	C4—C5	1.432 (4)
Cr1—O2	1.9655 (18)	C5—C6	1.347 (4)
Cr1—N1	2.067 (2)	C5—H5	0.9300
Cr1—N2	2.067 (2)	C6—C7	1.433 (4)
Ni1—N4	1.910 (2)	C6—H6	0.9300
Ni1—N4ⁱ	1.910 (2)	C7—C11	1.399 (3)
Ni1—N3	1.915 (2)	C7—C8	1.406 (4)
Ni1—N3ⁱ	1.915 (2)	C8—C9	1.358 (4)
N1—C1	1.332 (3)	C8—H8	0.9300
N1—C12	1.364 (3)	C9—C10	1.399 (4)
N2—C10	1.328 (3)	C9—H9	0.9300
N2—C11	1.362 (3)	C10—H10	0.9300
N3—C18	1.440 (4)	C11—C12	1.427 (3)
N3—C19	1.504 (3)	C13—C14	1.542 (4)
N3—H4	0.9000	C15—C16	1.555 (4)
N4—C23	1.277 (3)	C17—C18	1.475 (4)
N4—C17	1.473 (4)	C17—H17A	0.9700
O1—C14	1.287 (3)	C17—H17B	0.9700
O2—C13	1.287 (3)	C18—H18A	0.9700
O3—C16	1.285 (3)	C18—H18B	0.9700
O4—C15	1.288 (3)	C19—C20	1.511 (5)
O5—C14	1.222 (3)	C19—C22	1.515 (4)
O6—C13	1.220 (3)	C19—C21	1.534 (4)
O7—C15	1.215 (3)	C20—H20A	0.9600
O8—C16	1.211 (3)	C20—H20B	0.9600
O1W—H1A	0.90 (4)	C20—H20C	0.9600
O1W—H1B	0.90 (4)	C21—H21A	0.9600
O2W—H2A	0.92 (12)	C21—H21B	0.9600
O3W—H3A	0.91 (6)	C21—H21C	0.9600
O3W—H3B	0.90 (6)	C22—C23ⁱ	1.479 (4)
O4W—H4A	0.92 (7)	C22—H22A	0.9700
O4W—H4B	0.92 (5)	C22—H22B	0.9700
C1—C2	1.393 (4)	C23—C22ⁱ	1.479 (4)
C1—H1	0.9300	C23—C24	1.499 (4)
C2—C3	1.366 (4)	C24—H24A	0.9600
C2—H2	0.9300	C24—H24B	0.9600
C3—C4	1.407 (4)	C24—H24C	0.9600

O4—Cr1—O1	94.43 (8)	C8—C9—H9	120.1
O4—Cr1—O3	82.52 (7)	C10—C9—H9	120.1
O1—Cr1—O3	94.79 (8)	N2—C10—C9	122.4 (3)
O4—Cr1—O2	92.87 (8)	N2—C10—H10	118.8
O1—Cr1—O2	82.63 (8)	C9—C10—H10	118.8
O3—Cr1—O2	174.54 (8)	N2—C11—C7	123.1 (2)
O4—Cr1—N1	93.57 (8)	N2—C11—C12	116.7 (2)
O1—Cr1—N1	169.96 (8)	C7—C11—C12	120.1 (2)
O3—Cr1—N1	92.25 (8)	N1—C12—C4	123.0 (2)
O2—Cr1—N1	90.93 (8)	N1—C12—C11	117.0 (2)
O4—Cr1—N2	167.51 (8)	C4—C12—C11	120.0 (2)
O1—Cr1—N2	93.14 (8)	O6—C13—O2	126.0 (3)
O3—Cr1—N2	86.98 (8)	O6—C13—C14	120.3 (3)
O2—Cr1—N2	97.94 (8)	O2—C13—C14	113.6 (2)
N1—Cr1—N2	80.08 (8)	O5—C14—O1	125.4 (3)
N4—Ni1—N4ⁱ	180.0	O5—C14—C13	120.5 (3)
N4—Ni1—N3	85.68 (9)	O1—C14—C13	114.1 (2)
N4ⁱ—Ni1—N3	94.32 (9)	O7—C15—O4	125.8 (2)
N4—Ni1—N3ⁱ	94.32 (9)	O7—C15—C16	120.9 (2)
N4ⁱ—Ni1—N3ⁱ	85.68 (9)	O4—C15—C16	113.3 (2)
N3—Ni1—N3ⁱ	180.0	O8—C16—O3	125.9 (2)
C1—N1—C12	118.1 (2)	O8—C16—C15	120.6 (2)
C1—N1—Cr1	129.11 (18)	O3—C16—C15	113.5 (2)
C12—N1—Cr1	112.79 (15)	N4—C17—C18	107.3 (2)
C10—N2—C11	118.0 (2)	N4—C17—H17A	110.3
C10—N2—Cr1	128.56 (18)	C18—C17—H17A	110.3
C11—N2—Cr1	112.81 (15)	N4—C17—H17B	110.3
C18—N3—C19	114.6 (3)	C18—C17—H17B	110.3
C18—N3—Ni1	109.6 (2)	H17A—C17—H17B	108.5
C19—N3—Ni1	119.36 (18)	N3—C18—C17	110.2 (3)
C18—N3—H4	108.6	N3—C18—H18A	109.6
C19—N3—H4	108.6	C17—C18—H18A	109.6
Ni1—N3—H4	93.7	N3—C18—H18B	109.6
C23—N4—C17	119.1 (2)	C17—C18—H18B	109.6
C23—N4—Ni1	128.6 (2)	H18A—C18—H18B	108.1
C17—N4—Ni1	112.21 (16)	N3—C19—C20	111.1 (3)
C14—O1—Cr1	114.49 (16)	N3—C19—C22	105.1 (2)
C13—O2—Cr1	114.04 (17)	C20—C19—C22	111.4 (3)
C16—O3—Cr1	115.05 (15)	N3—C19—C21	110.1 (2)
C15—O4—Cr1	115.20 (16)	C20—C19—C21	110.5 (3)
H1A—O1W—H1B	98 (3)	C22—C19—C21	108.5 (3)
H3A—O3W—H3B	96 (4)	C19—C20—H20A	109.5
H4A—O4W—H4B	94 (4)	C19—C20—H20B	109.5
N1—C1—C2	122.2 (3)	H20A—C20—H20B	109.5
N1—C1—H1	118.9	C19—C20—H20C	109.5
C2—C1—H1	118.9	H20A—C20—H20C	109.5
C3—C2—C1	120.2 (2)	H20B—C20—H20C	109.5
C3—C2—H2	119.9	C19—C21—H21A	109.5
C1—C2—H2	119.9	C19—C21—H21B	109.5
C2—C3—C4	119.4 (2)	H21A—C21—H21B	109.5
C2—C3—H3	120.3	C19—C21—H21C	109.5
C4—C3—H3	120.3	H21A—C21—H21C	109.5
C12—C4—C3	117.0 (2)	H21B—C21—H21C	109.5
C12—C4—C5	118.5 (2)	C23ⁱ—C22—C19	118.3 (2)
C3—C4—C5	124.4 (2)	C23ⁱ—C22—H22A	107.7
C6—C5—C4	121.4 (2)	C19—C22—H22A	107.7
C6—C5—H5	119.3	C23ⁱ—C22—H22B	107.7
C4—C5—H5	119.3	C19—C22—H22B	107.7
C5—C6—C7	121.1 (2)	H22A—C22—H22B	107.1
C5—C6—H6	119.5	N4—C23—C22ⁱ	121.1 (2)
C7—C6—H6	119.5	N4—C23—C24	123.8 (3)
C11—C7—C8	117.0 (2)	C22ⁱ—C23—C24	115.1 (3)
C11—C7—C6	118.7 (2)	C23—C24—H24A	109.5
C8—C7—C6	124.2 (2)	C23—C24—H24B	109.5
C9—C8—C7	119.7 (2)	H24A—C24—H24B	109.5
C9—C8—H8	120.1	C23—C24—H24C	109.5
C7—C8—H8	120.1	H24A—C24—H24C	109.5
C8—C9—C10	119.8 (3)	H24B—C24—H24C	109.5

O4—Cr1—N1—C1	−16.3 (2)	C7—C8—C9—C10	0.1 (5)
O1—Cr1—N1—C1	126.5 (4)	C11—N2—C10—C9	0.2 (4)
O3—Cr1—N1—C1	−99.0 (2)	Cr1—N2—C10—C9	−169.7 (2)
O2—Cr1—N1—C1	76.6 (2)	C8—C9—C10—N2	−0.6 (5)
N2—Cr1—N1—C1	174.5 (2)	C10—N2—C11—C7	0.8 (4)
O4—Cr1—N1—C12	163.80 (16)	Cr1—N2—C11—C7	172.15 (19)
O1—Cr1—N1—C12	−53.4 (5)	C10—N2—C11—C12	−179.3 (2)
O3—Cr1—N1—C12	81.16 (16)	Cr1—N2—C11—C12	−7.9 (3)
O2—Cr1—N1—C12	−103.27 (17)	C8—C7—C11—N2	−1.3 (4)
N2—Cr1—N1—C12	−5.37 (16)	C6—C7—C11—N2	178.4 (2)
O4—Cr1—N2—C10	117.2 (4)	C8—C7—C11—C12	178.8 (2)
O1—Cr1—N2—C10	−10.1 (2)	C6—C7—C11—C12	−1.6 (4)
O3—Cr1—N2—C10	84.6 (2)	C1—N1—C12—C4	2.6 (3)
O2—Cr1—N2—C10	−93.0 (2)	Cr1—N1—C12—C4	−177.50 (18)
N1—Cr1—N2—C10	177.4 (2)	C1—N1—C12—C11	−177.0 (2)
O4—Cr1—N2—C11	−53.0 (5)	Cr1—N1—C12—C11	2.9 (3)
O1—Cr1—N2—C11	179.70 (17)	C3—C4—C12—N1	−2.6 (4)
O3—Cr1—N2—C11	−85.67 (17)	C5—C4—C12—N1	177.4 (2)
O2—Cr1—N2—C11	96.71 (17)	C3—C4—C12—C11	177.0 (2)
N1—Cr1—N2—C11	7.15 (16)	C5—C4—C12—C11	−3.0 (3)
N4—Ni1—N3—C18	−18.1 (3)	N2—C11—C12—N1	3.4 (3)
N4ⁱ—Ni1—N3—C18	161.9 (3)	C7—C11—C12—N1	−176.6 (2)
N4—Ni1—N3—C19	−153.1 (2)	N2—C11—C12—C4	−176.2 (2)
N4ⁱ—Ni1—N3—C19	26.9 (2)	C7—C11—C12—C4	3.7 (4)
N3—Ni1—N4—C23	172.3 (3)	Cr1—O2—C13—O6	167.8 (3)
N3ⁱ—Ni1—N4—C23	−7.7 (3)	Cr1—O2—C13—C14	−11.4 (3)
N3—Ni1—N4—C17	−5.3 (2)	Cr1—O1—C14—O5	179.7 (2)
N3ⁱ—Ni1—N4—C17	174.7 (2)	Cr1—O1—C14—C13	−0.2 (3)
O4—Cr1—O1—C14	87.81 (19)	O6—C13—C14—O5	8.7 (5)
O3—Cr1—O1—C14	170.65 (18)	O2—C13—C14—O5	−172.0 (3)
O2—Cr1—O1—C14	−4.51 (19)	O6—C13—C14—O1	−171.4 (3)
N1—Cr1—O1—C14	−55.0 (5)	O2—C13—C14—O1	7.8 (4)
N2—Cr1—O1—C14	−102.12 (19)	Cr1—O4—C15—O7	−172.3 (2)
O4—Cr1—O2—C13	−84.9 (2)	Cr1—O4—C15—C16	7.5 (3)
O1—Cr1—O2—C13	9.18 (19)	Cr1—O3—C16—O8	−178.8 (2)
N1—Cr1—O2—C13	−178.55 (19)	Cr1—O3—C16—C15	0.5 (3)
N2—Cr1—O2—C13	101.3 (2)	O7—C15—C16—O8	−6.2 (4)
O4—Cr1—O3—C16	2.66 (18)	O4—C15—C16—O8	174.0 (3)
O1—Cr1—O3—C16	−91.20 (18)	O7—C15—C16—O3	174.5 (2)
N1—Cr1—O3—C16	95.96 (18)	O4—C15—C16—O3	−5.3 (3)
N2—Cr1—O3—C16	175.90 (18)	C23—N4—C17—C18	−151.2 (3)
O1—Cr1—O4—C15	88.36 (18)	Ni1—N4—C17—C18	26.7 (3)
O3—Cr1—O4—C15	−5.90 (18)	C19—N3—C18—C17	175.4 (3)
O2—Cr1—O4—C15	171.19 (18)	Ni1—N3—C18—C17	38.0 (4)
N1—Cr1—O4—C15	−97.70 (18)	N4—C17—C18—N3	−41.7 (4)
N2—Cr1—O4—C15	−38.8 (5)	C18—N3—C19—C20	−71.9 (4)
C12—N1—C1—C2	−0.5 (4)	Ni1—N3—C19—C20	61.0 (3)
Cr1—N1—C1—C2	179.7 (2)	C18—N3—C19—C22	167.5 (3)
N1—C1—C2—C3	−1.6 (4)	Ni1—N3—C19—C22	−59.6 (3)
C1—C2—C3—C4	1.5 (4)	C18—N3—C19—C21	50.8 (4)
C2—C3—C4—C12	0.5 (4)	Ni1—N3—C19—C21	−176.3 (2)
C2—C3—C4—C5	−179.5 (3)	N3—C19—C22—C23ⁱ	64.9 (4)
C12—C4—C5—C6	0.1 (4)	C20—C19—C22—C23ⁱ	−55.5 (4)
C3—C4—C5—C6	−179.9 (3)	C21—C19—C22—C23ⁱ	−177.4 (3)
C4—C5—C6—C7	2.1 (4)	C17—N4—C23—C22ⁱ	−177.6 (3)
C5—C6—C7—C11	−1.3 (4)	Ni1—N4—C23—C22ⁱ	4.9 (4)
C5—C6—C7—C8	178.3 (3)	C17—N4—C23—C24	2.5 (4)
C11—C7—C8—C9	0.8 (4)	Ni1—N4—C23—C24	−175.0 (2)
C6—C7—C8—C9	−178.8 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4···O3Wⁱⁱ	0.90	2.03	2.927 (4)	171
O3W—H3B···O6ⁱⁱ	0.90 (6)	2.38 (6)	3.104 (5)	138 (4)
O3W—H3A···O1W	0.91 (6)	2.02 (6)	2.857 (4)	152 (5)
O4W—H4B···O2Wⁱⁱⁱ	0.92 (5)	1.96 (5)	2.799 (5)	152 (4)
O2W—H2A···O5	0.92 (12)	1.94 (12)	2.835 (4)	163 (11)
O1W—H1B···O7	0.90 (4)	2.00 (4)	2.871 (3)	164 (4)
O1W—H1A···O8^iv	0.90 (4)	1.97 (4)	2.866 (3)	176 (4)

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

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