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Macrocyclic ligand systems with a variety of (different) donor sites oftentimes give rise to very exciting and unexpected multinuclear metal complexes. We report herein the structure of a trinuclear mixed imidazolyl­idene/imidazolium nickel N-heterocyclic carbene (NHC) complex, namely di-μ-chlorido-bis{μ-calix[2]imidazolium[2]imidazolylidene[2]pyrazolate}trinickel(II) tetrakis(hexafluoridophosphate) acetonitrile tetrasolvate, [Ni3(C24H24N12)2Cl2](PF6)4·4CH3CN or [Ni3(LMe)2Cl2](PF6)4·4CH3CN, that can be understood as a trapped reaction inter­mediate during the synthesis of the respective [Ni2LMe](PF6)2 product. The structure not only contains protonated next to deprotonated imidazole heterocycles, but also Ni2+ ions with fundamentally different coordination modes within one mol­ecule. Two of the three metal atoms are coordinated in a square-pyramidal fashion by half a ligand mol­ecule and one chloride ligand, whereas the third Ni2+ ion is bound octa­hedrally by four pyrazolate moieties and two chloride anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013250/fp3043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013250/fp3043Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2053229617013250/fp3043Isup3.cdx
Supplementary material

png

Portable Network Graphics (PNG) image https://doi.org/10.1107/S2053229617013250/fp3043sup4.png
TOC graphic

CCDC reference: 1568200

Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015), SHELXLE (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009), enCIFer (Allen et al., 2004).

Di-µ-chlorido-bis{µ-calix[2]imidazolium[2]imidazolylidene[2]pyrazolate}trinickel(II) tetrakis(hexafluoridophosphate) acetonitrile tetrasolvate top
Crystal data top
[Ni3(C24H24N12)2Cl2](PF6)4·4C2H3NZ = 1
Mr = 1952.17F(000) = 986
Triclinic, P1Dx = 1.778 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.8775 (9) ÅCell parameters from 9868 reflections
b = 13.3374 (9) Åθ = 2.3–32.0°
c = 13.9741 (9) ŵ = 1.05 mm1
α = 66.056 (3)°T = 100 K
β = 73.926 (3)°Fragment, clear yellow
γ = 65.297 (3)°0.20 × 0.13 × 0.08 mm
V = 1822.7 (2) Å3
Data collection top
Bruker Photon CMOS
diffractometer
9819 independent reflections
Radiation source: IMS microsource7472 reflections with I > 2σ(I)
Helios optic monochromatorRint = 0.061
Detector resolution: 16 pixels mm-1θmax = 29.1°, θmin = 2.3°
phi– and ω–rotation scansh = 1616
Absorption correction: multi-scan
SADABS 2014/5, Bruker, 2014
k = 1818
Tmin = 0.673, Tmax = 0.746l = 1919
51283 measured reflections
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 W = 1/[Σ2(FO2) + (0.0381P)2 + 2.3353P] WHERE P = (FO2 + 2FC2)/3
S = 1.02(Δ/σ)max < 0.001
9819 reflectionsΔρmax = 1.67 e Å3
539 parametersΔρmin = 0.77 e Å3
Special details top

Experimental. Diffractometer operator Philipp J. Altmann scanspeed 60 s per frame dx 34 mm 6428 frames measured in 23 data sets phi-scans with delta_phi = 0.5 omega-scans with delta_omega = 0.5

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
Ni10.18222 (3)0.27876 (2)0.68985 (2)0.00985 (7)
Ni20.00000.50000.50000.00856 (9)
Cl10.04051 (5)0.42980 (5)0.69365 (4)0.01104 (11)
N10.25435 (18)0.39455 (17)0.16855 (15)0.0134 (4)
N20.09296 (18)0.34947 (17)0.26072 (15)0.0124 (4)
N30.07904 (17)0.32379 (16)0.50325 (14)0.0096 (4)
N40.14200 (17)0.24252 (16)0.58621 (14)0.0107 (4)
N50.17948 (19)0.04291 (17)0.77712 (15)0.0145 (4)
N60.12259 (18)0.12316 (17)0.89528 (15)0.0139 (4)
N70.19490 (19)0.25883 (17)0.90073 (15)0.0148 (4)
N80.33596 (19)0.31899 (17)0.78935 (16)0.0145 (4)
N90.23851 (17)0.40452 (16)0.59363 (14)0.0106 (4)
N100.17849 (17)0.49036 (16)0.51056 (14)0.0098 (4)
N110.27539 (18)0.63160 (17)0.27492 (15)0.0127 (4)
N120.34110 (18)0.52256 (17)0.17706 (15)0.0133 (4)
C10.3689 (2)0.4192 (2)0.14945 (19)0.0148 (5)
H1A0.40420.43320.07410.018*
H1B0.43140.35120.19260.018*
C20.2079 (2)0.3379 (2)0.26376 (19)0.0129 (4)
C30.1633 (2)0.4470 (2)0.10200 (19)0.0164 (5)
H30.17020.49410.02980.020*
C40.0632 (2)0.4182 (2)0.15988 (18)0.0161 (5)
H40.01400.44090.13570.019*
C50.0014 (2)0.3201 (2)0.35500 (17)0.0129 (4)
H5A0.03140.26630.34850.015*
H5B0.06970.39230.35860.015*
C60.0612 (2)0.2636 (2)0.45378 (18)0.0123 (4)
C70.1098 (2)0.1443 (2)0.50590 (19)0.0151 (5)
H70.10920.08280.48840.018*
C80.1592 (2)0.1350 (2)0.58914 (19)0.0146 (5)
C90.2220 (3)0.0272 (2)0.67348 (19)0.0192 (5)
H9A0.20350.03940.67530.023*
H9B0.31360.00850.65710.023*
C100.1554 (2)0.1445 (2)0.79008 (18)0.0134 (4)
C110.1660 (2)0.0428 (2)0.87331 (19)0.0182 (5)
H110.17880.12170.88430.022*
C120.1312 (2)0.0077 (2)0.9480 (2)0.0178 (5)
H120.11560.02871.02210.021*
C130.0920 (2)0.2148 (2)0.93958 (19)0.0170 (5)
H13A0.01310.27840.91690.020*
H13B0.08170.18271.01770.020*
C140.2382 (2)0.28962 (19)0.79639 (18)0.0135 (4)
C150.2678 (3)0.2655 (2)0.9583 (2)0.0191 (5)
H150.25750.24661.03270.023*
C160.3560 (3)0.3041 (2)0.8881 (2)0.0200 (5)
H160.42000.31850.90310.024*
C170.4114 (2)0.3571 (2)0.68931 (19)0.0159 (5)
H17A0.47470.28780.67180.019*
H17B0.45610.40170.69600.019*
C180.3314 (2)0.4322 (2)0.60247 (18)0.0119 (4)
C190.3354 (2)0.5352 (2)0.52378 (18)0.0133 (4)
H190.39160.57440.51100.016*
C200.2386 (2)0.56861 (19)0.46741 (17)0.0111 (4)
C210.2088 (2)0.6697 (2)0.36821 (17)0.0129 (4)
H21A0.11760.70200.36570.016*
H21B0.23450.73200.36680.016*
C220.3116 (2)0.5231 (2)0.27621 (18)0.0123 (4)
C230.2803 (2)0.7043 (2)0.17070 (19)0.0184 (5)
H230.25890.78680.14670.022*
C240.3213 (2)0.6360 (2)0.10939 (19)0.0181 (5)
H240.33400.66120.03440.022*
H20.248 (2)0.298 (2)0.322 (2)0.010 (6)*
H220.316 (2)0.459 (2)0.336 (2)0.015 (7)*
P10.80480 (7)0.00924 (6)0.76308 (5)0.02291 (15)
F10.88392 (16)0.05572 (15)0.77728 (14)0.0315 (4)
F20.72555 (18)0.07490 (16)0.75257 (15)0.0378 (4)
F30.69023 (15)0.11300 (13)0.73112 (13)0.0287 (4)
F40.8644 (2)0.01359 (18)0.64277 (14)0.0434 (5)
F50.91719 (18)0.13127 (15)0.79802 (15)0.0410 (5)
F60.74400 (15)0.02860 (15)0.88527 (12)0.0299 (4)
P20.71199 (6)0.35070 (6)0.19854 (5)0.01652 (13)
F70.77596 (15)0.43748 (14)0.19221 (15)0.0308 (4)
F80.64811 (14)0.26367 (14)0.20333 (14)0.0275 (4)
F90.82073 (15)0.30684 (14)0.11073 (13)0.0292 (4)
F100.79073 (15)0.24998 (14)0.29032 (14)0.0307 (4)
F110.60129 (15)0.39598 (15)0.28365 (13)0.0292 (4)
F120.63129 (14)0.45153 (14)0.10512 (12)0.0256 (3)
N130.4955 (2)0.2079 (2)0.9165 (2)0.0289 (5)
C250.4749 (3)0.1115 (2)0.8972 (2)0.0239 (6)
C260.4477 (3)0.0122 (3)0.8749 (3)0.0360 (7)
H26A0.52480.02500.87020.054*
H26B0.38680.03730.93170.054*
H26C0.41300.05770.80780.054*
N140.4185 (3)0.2205 (3)0.4152 (2)0.0551 (8)
C270.5005 (3)0.1757 (4)0.4612 (3)0.0503 (8)
C280.6071 (4)0.1257 (4)0.5191 (3)0.0611 (9)
H28A0.64870.04260.52630.092*
H28B0.57810.13360.58940.092*
H28C0.66610.16710.48060.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01309 (14)0.00777 (14)0.00867 (13)0.00374 (11)0.00414 (10)0.00081 (11)
Ni20.00964 (19)0.00759 (19)0.00830 (18)0.00324 (15)0.00262 (14)0.00133 (15)
Cl10.0112 (2)0.0110 (2)0.0101 (2)0.00318 (19)0.00209 (19)0.0030 (2)
N10.0128 (9)0.0129 (9)0.0144 (9)0.0035 (8)0.0003 (7)0.0064 (8)
N20.0141 (9)0.0126 (9)0.0120 (9)0.0044 (8)0.0010 (7)0.0061 (8)
N30.0110 (9)0.0092 (9)0.0076 (8)0.0026 (7)0.0028 (7)0.0016 (7)
N40.0118 (9)0.0087 (9)0.0098 (9)0.0022 (7)0.0040 (7)0.0010 (7)
N50.0195 (10)0.0102 (9)0.0128 (9)0.0053 (8)0.0050 (8)0.0007 (8)
N60.0170 (10)0.0105 (9)0.0108 (9)0.0040 (8)0.0040 (7)0.0004 (8)
N70.0203 (10)0.0117 (9)0.0106 (9)0.0034 (8)0.0059 (8)0.0018 (8)
N80.0202 (10)0.0113 (9)0.0135 (9)0.0056 (8)0.0096 (8)0.0007 (8)
N90.0126 (9)0.0091 (9)0.0098 (9)0.0030 (7)0.0048 (7)0.0015 (7)
N100.0110 (9)0.0087 (9)0.0081 (8)0.0024 (7)0.0020 (7)0.0017 (7)
N110.0144 (9)0.0126 (9)0.0102 (9)0.0058 (8)0.0019 (7)0.0015 (8)
N120.0117 (9)0.0156 (10)0.0125 (9)0.0057 (8)0.0001 (7)0.0043 (8)
C10.0110 (11)0.0171 (12)0.0174 (11)0.0047 (9)0.0019 (9)0.0094 (10)
C20.0138 (11)0.0117 (11)0.0134 (11)0.0031 (9)0.0025 (9)0.0052 (9)
C30.0183 (12)0.0218 (12)0.0109 (11)0.0080 (10)0.0024 (9)0.0058 (10)
C40.0179 (12)0.0217 (12)0.0113 (11)0.0080 (10)0.0030 (9)0.0059 (10)
C50.0141 (11)0.0166 (11)0.0107 (10)0.0086 (9)0.0008 (8)0.0044 (9)
C60.0132 (11)0.0141 (11)0.0111 (10)0.0072 (9)0.0001 (8)0.0042 (9)
C70.0210 (12)0.0131 (11)0.0156 (11)0.0086 (9)0.0022 (9)0.0063 (9)
C80.0191 (12)0.0099 (11)0.0144 (11)0.0055 (9)0.0024 (9)0.0029 (9)
C90.0296 (14)0.0114 (11)0.0166 (12)0.0049 (10)0.0074 (10)0.0040 (10)
C100.0137 (11)0.0110 (11)0.0144 (11)0.0035 (9)0.0053 (9)0.0017 (9)
C110.0223 (12)0.0095 (11)0.0177 (12)0.0063 (10)0.0065 (10)0.0038 (9)
C120.0187 (12)0.0150 (12)0.0159 (11)0.0074 (10)0.0050 (9)0.0019 (9)
C130.0201 (12)0.0147 (11)0.0130 (11)0.0035 (10)0.0037 (9)0.0033 (9)
C140.0172 (11)0.0070 (10)0.0136 (11)0.0005 (9)0.0070 (9)0.0015 (9)
C150.0327 (14)0.0127 (11)0.0144 (11)0.0062 (10)0.0114 (10)0.0033 (9)
C160.0325 (14)0.0133 (12)0.0182 (12)0.0073 (10)0.0164 (11)0.0012 (10)
C170.0142 (11)0.0163 (12)0.0172 (12)0.0057 (9)0.0068 (9)0.0019 (10)
C180.0100 (10)0.0128 (11)0.0138 (11)0.0028 (8)0.0034 (8)0.0054 (9)
C190.0128 (11)0.0130 (11)0.0145 (11)0.0060 (9)0.0033 (9)0.0025 (9)
C200.0127 (10)0.0108 (10)0.0109 (10)0.0046 (8)0.0010 (8)0.0043 (9)
C210.0156 (11)0.0127 (11)0.0111 (10)0.0067 (9)0.0008 (9)0.0034 (9)
C220.0106 (10)0.0133 (11)0.0123 (11)0.0044 (9)0.0008 (8)0.0038 (9)
C230.0249 (13)0.0164 (12)0.0119 (11)0.0099 (10)0.0040 (9)0.0010 (9)
C240.0217 (12)0.0193 (12)0.0122 (11)0.0098 (10)0.0022 (9)0.0012 (10)
P10.0367 (4)0.0157 (3)0.0175 (3)0.0094 (3)0.0092 (3)0.0027 (3)
F10.0342 (9)0.0317 (9)0.0373 (10)0.0121 (8)0.0119 (8)0.0142 (8)
F20.0467 (11)0.0312 (10)0.0490 (11)0.0215 (8)0.0083 (9)0.0165 (9)
F30.0321 (9)0.0175 (8)0.0331 (9)0.0090 (7)0.0149 (7)0.0021 (7)
F40.0637 (13)0.0552 (13)0.0200 (9)0.0312 (11)0.0007 (8)0.0131 (9)
F50.0466 (11)0.0230 (9)0.0413 (11)0.0023 (8)0.0068 (9)0.0134 (8)
F60.0306 (9)0.0313 (9)0.0177 (8)0.0069 (7)0.0042 (7)0.0018 (7)
P20.0147 (3)0.0152 (3)0.0211 (3)0.0047 (2)0.0062 (2)0.0054 (3)
F70.0246 (8)0.0186 (8)0.0545 (11)0.0081 (7)0.0145 (8)0.0104 (8)
F80.0229 (8)0.0231 (8)0.0436 (10)0.0100 (7)0.0084 (7)0.0131 (8)
F90.0221 (8)0.0272 (9)0.0308 (9)0.0050 (7)0.0042 (7)0.0112 (7)
F100.0308 (9)0.0224 (8)0.0363 (10)0.0044 (7)0.0197 (7)0.0021 (7)
F110.0261 (8)0.0325 (9)0.0294 (9)0.0053 (7)0.0017 (7)0.0170 (8)
F120.0247 (8)0.0224 (8)0.0220 (8)0.0035 (7)0.0106 (6)0.0002 (6)
N130.0326 (13)0.0243 (13)0.0325 (13)0.0062 (10)0.0128 (11)0.0100 (11)
C250.0228 (13)0.0228 (14)0.0266 (14)0.0046 (11)0.0102 (11)0.0077 (12)
C260.0252 (15)0.0189 (14)0.059 (2)0.0036 (12)0.0078 (14)0.0111 (14)
N140.0364 (14)0.0775 (19)0.0378 (14)0.0161 (13)0.0158 (11)0.0030 (14)
C270.0385 (14)0.0704 (17)0.0355 (13)0.0061 (13)0.0142 (11)0.0187 (13)
C280.0464 (17)0.080 (2)0.0433 (16)0.0062 (16)0.0205 (14)0.0269 (16)
Geometric parameters (Å, º) top
Ni1—C101.861 (2)C6—C71.386 (3)
Ni1—C141.866 (2)C7—C81.383 (3)
Ni1—N91.9176 (19)C7—H70.9500
Ni1—N41.9245 (19)C8—C91.492 (3)
Ni1—Cl12.5718 (6)C9—H9A0.9900
Ni2—N10i2.1126 (18)C9—H9B0.9900
Ni2—N102.1126 (18)C11—C121.346 (4)
Ni2—N3i2.1213 (18)C11—H110.9500
Ni2—N32.1213 (18)C12—H120.9500
Ni2—Cl12.4556 (5)C13—H13A0.9900
Ni2—Cl1i2.4556 (5)C13—H13B0.9900
N1—C21.331 (3)C15—C161.340 (4)
N1—C31.386 (3)C15—H150.9500
N1—C11.460 (3)C16—H160.9500
N2—C21.319 (3)C17—C181.496 (3)
N2—C41.381 (3)C17—H17A0.9900
N2—C51.488 (3)C17—H17B0.9900
N3—C61.356 (3)C18—C191.377 (3)
N3—N41.364 (2)C19—C201.389 (3)
N4—C81.347 (3)C19—H190.9500
N5—C101.341 (3)C20—C211.490 (3)
N5—C111.388 (3)C21—H21A0.9900
N5—C91.466 (3)C21—H21B0.9900
N6—C101.353 (3)C22—H220.92 (3)
N6—C121.384 (3)C23—C241.354 (4)
N6—C131.458 (3)C23—H230.9500
N7—C141.354 (3)C24—H240.9500
N7—C151.384 (3)P1—F41.5895 (19)
N7—C131.452 (3)P1—F21.5951 (18)
N8—C141.341 (3)P1—F51.6030 (19)
N8—C161.385 (3)P1—F11.6114 (17)
N8—C171.458 (3)P1—F31.6126 (17)
N9—C181.350 (3)P1—F61.6184 (17)
N9—N101.365 (2)P2—F71.5936 (16)
N10—C201.355 (3)P2—F101.5937 (17)
N11—C221.320 (3)P2—F111.6005 (17)
N11—C231.385 (3)P2—F81.6038 (16)
N11—C211.488 (3)P2—F91.6092 (17)
N12—C221.334 (3)P2—F121.6193 (16)
N12—C241.379 (3)N13—C251.131 (4)
N12—C11.463 (3)C25—C261.455 (4)
C1—H1A0.9900C26—H26A0.9800
C1—H1B0.9900C26—H26B0.9800
C2—H20.91 (3)C26—H26C0.9800
C3—C41.347 (3)N14—C271.125 (4)
C3—H30.9500C27—C281.458 (5)
C4—H40.9500C28—H28A0.9800
C5—C61.493 (3)C28—H28B0.9800
C5—H5A0.9900C28—H28C0.9800
C5—H5B0.9900
C10—Ni1—C1486.29 (10)N5—C10—N6104.57 (19)
C10—Ni1—N9170.02 (9)N5—C10—Ni1128.00 (18)
C14—Ni1—N987.53 (9)N6—C10—Ni1126.93 (18)
C10—Ni1—N487.91 (9)C12—C11—N5106.6 (2)
C14—Ni1—N4171.02 (9)C12—C11—H11126.7
N9—Ni1—N497.24 (8)N5—C11—H11126.7
C10—Ni1—Cl1100.88 (7)C11—C12—N6106.2 (2)
C14—Ni1—Cl1100.19 (7)C11—C12—H12126.9
N9—Ni1—Cl187.92 (6)N6—C12—H12126.9
N4—Ni1—Cl187.63 (6)N7—C13—N6106.87 (19)
N10i—Ni2—N10180.00 (10)N7—C13—H13A110.3
N10i—Ni2—N3i88.87 (7)N6—C13—H13A110.3
N10—Ni2—N3i91.13 (7)N7—C13—H13B110.3
N10i—Ni2—N391.13 (7)N6—C13—H13B110.3
N10—Ni2—N388.87 (7)H13A—C13—H13B108.6
N3i—Ni2—N3180.00 (10)N8—C14—N7104.5 (2)
N10i—Ni2—Cl190.74 (5)N8—C14—Ni1128.36 (18)
N10—Ni2—Cl189.26 (5)N7—C14—Ni1126.92 (18)
N3i—Ni2—Cl190.83 (5)C16—C15—N7106.3 (2)
N3—Ni2—Cl189.17 (5)C16—C15—H15126.9
N10i—Ni2—Cl1i89.26 (5)N7—C15—H15126.9
N10—Ni2—Cl1i90.74 (5)C15—C16—N8106.9 (2)
N3i—Ni2—Cl1i89.17 (5)C15—C16—H16126.5
N3—Ni2—Cl1i90.83 (5)N8—C16—H16126.5
Cl1—Ni2—Cl1i180.0N8—C17—C18110.79 (19)
Ni2—Cl1—Ni186.701 (18)N8—C17—H17A109.5
C2—N1—C3108.40 (19)C18—C17—H17A109.5
C2—N1—C1123.0 (2)N8—C17—H17B109.5
C3—N1—C1126.9 (2)C18—C17—H17B109.5
C2—N2—C4108.3 (2)H17A—C17—H17B108.1
C2—N2—C5124.97 (19)N9—C18—C19109.94 (19)
C4—N2—C5125.05 (19)N9—C18—C17121.3 (2)
C6—N3—N4106.63 (18)C19—C18—C17128.8 (2)
C6—N3—Ni2134.34 (15)C18—C19—C20104.4 (2)
N4—N3—Ni2117.30 (13)C18—C19—H19127.8
C8—N4—N3108.90 (18)C20—C19—H19127.8
C8—N4—Ni1126.18 (15)N10—C20—C19110.4 (2)
N3—N4—Ni1124.60 (14)N10—C20—C21123.21 (19)
C10—N5—C11111.2 (2)C19—C20—C21126.2 (2)
C10—N5—C9122.3 (2)N11—C21—C20110.05 (18)
C11—N5—C9126.3 (2)N11—C21—H21A109.7
C10—N6—C12111.3 (2)C20—C21—H21A109.7
C10—N6—C13120.13 (19)N11—C21—H21B109.7
C12—N6—C13128.5 (2)C20—C21—H21B109.7
C14—N7—C15111.2 (2)H21A—C21—H21B108.2
C14—N7—C13120.2 (2)N11—C22—N12109.0 (2)
C15—N7—C13128.4 (2)N11—C22—H22124.8 (17)
C14—N8—C16111.1 (2)N12—C22—H22126.2 (17)
C14—N8—C17122.66 (19)C24—C23—N11107.3 (2)
C16—N8—C17126.2 (2)C24—C23—H23126.3
C18—N9—N10108.49 (18)N11—C23—H23126.3
C18—N9—Ni1127.13 (15)C23—C24—N12106.6 (2)
N10—N9—Ni1123.91 (14)C23—C24—H24126.7
C20—N10—N9106.79 (17)N12—C24—H24126.7
C20—N10—Ni2132.83 (15)F4—P1—F291.74 (11)
N9—N10—Ni2118.10 (14)F4—P1—F590.84 (11)
C22—N11—C23108.4 (2)F2—P1—F590.21 (11)
C22—N11—C21123.80 (19)F4—P1—F189.84 (10)
C23—N11—C21125.9 (2)F2—P1—F1178.38 (11)
C22—N12—C24108.7 (2)F5—P1—F189.41 (10)
C22—N12—C1123.2 (2)F4—P1—F390.65 (11)
C24—N12—C1127.3 (2)F2—P1—F389.81 (10)
N1—C1—N12109.47 (18)F5—P1—F3178.50 (11)
N1—C1—H1A109.8F1—P1—F390.53 (9)
N12—C1—H1A109.8F4—P1—F6178.24 (11)
N1—C1—H1B109.8F2—P1—F689.69 (10)
N12—C1—H1B109.8F5—P1—F690.18 (10)
H1A—C1—H1B108.2F1—P1—F688.73 (10)
N2—C2—N1109.1 (2)F3—P1—F688.32 (9)
N2—C2—H2124.9 (16)F7—P2—F1090.77 (9)
N1—C2—H2125.9 (16)F7—P2—F1190.67 (10)
C4—C3—N1106.5 (2)F10—P2—F1190.77 (9)
C4—C3—H3126.8F7—P2—F8179.28 (10)
N1—C3—H3126.8F10—P2—F889.66 (9)
C3—C4—N2107.7 (2)F11—P2—F889.90 (9)
C3—C4—H4126.2F7—P2—F989.85 (10)
N2—C4—H4126.2F10—P2—F990.64 (9)
N2—C5—C6110.78 (18)F11—P2—F9178.49 (9)
N2—C5—H5A109.5F8—P2—F989.56 (9)
C6—C5—H5A109.5F7—P2—F1290.12 (9)
N2—C5—H5B109.5F10—P2—F12179.09 (9)
C6—C5—H5B109.5F11—P2—F1289.39 (9)
H5A—C5—H5B108.1F8—P2—F1289.44 (9)
N3—C6—C7110.4 (2)F9—P2—F1289.20 (9)
N3—C6—C5123.8 (2)N13—C25—C26178.8 (3)
C7—C6—C5125.7 (2)C25—C26—H26A109.5
C8—C7—C6104.5 (2)C25—C26—H26B109.5
C8—C7—H7127.8H26A—C26—H26B109.5
C6—C7—H7127.8C25—C26—H26C109.5
N4—C8—C7109.5 (2)H26A—C26—H26C109.5
N4—C8—C9121.7 (2)H26B—C26—H26C109.5
C7—C8—C9128.7 (2)N14—C27—C28176.0 (5)
N5—C9—C8111.1 (2)C27—C28—H28A109.5
N5—C9—H9A109.4C27—C28—H28B109.5
C8—C9—H9A109.4H28A—C28—H28B109.5
N5—C9—H9B109.4C27—C28—H28C109.5
C8—C9—H9B109.4H28A—C28—H28C109.5
H9A—C9—H9B108.0H28B—C28—H28C109.5
C6—N3—N4—C81.7 (2)C9—N5—C11—C12176.9 (2)
Ni2—N3—N4—C8165.49 (15)N5—C11—C12—N60.9 (3)
C6—N3—N4—Ni1175.50 (15)C10—N6—C12—C112.1 (3)
Ni2—N3—N4—Ni18.3 (2)C13—N6—C12—C11178.0 (2)
C18—N9—N10—C201.7 (2)C14—N7—C13—N649.5 (3)
Ni1—N9—N10—C20174.35 (15)C15—N7—C13—N6124.0 (2)
C18—N9—N10—Ni2163.28 (14)C10—N6—C13—N752.0 (3)
Ni1—N9—N10—Ni29.3 (2)C12—N6—C13—N7123.5 (2)
C2—N1—C1—N1281.1 (3)C16—N8—C14—N71.5 (3)
C3—N1—C1—N1282.2 (3)C17—N8—C14—N7179.4 (2)
C22—N12—C1—N170.5 (3)C16—N8—C14—Ni1173.07 (17)
C24—N12—C1—N198.4 (3)C17—N8—C14—Ni14.8 (3)
C4—N2—C2—N11.1 (3)C15—N7—C14—N81.9 (3)
C5—N2—C2—N1166.8 (2)C13—N7—C14—N8176.4 (2)
C3—N1—C2—N21.3 (3)C15—N7—C14—Ni1172.79 (17)
C1—N1—C2—N2167.3 (2)C13—N7—C14—Ni11.8 (3)
C2—N1—C3—C41.1 (3)C10—Ni1—C14—N8139.2 (2)
C1—N1—C3—C4166.3 (2)N9—Ni1—C14—N833.0 (2)
N1—C3—C4—N20.4 (3)Cl1—Ni1—C14—N8120.4 (2)
C2—N2—C4—C30.4 (3)C10—Ni1—C14—N734.3 (2)
C5—N2—C4—C3166.1 (2)N9—Ni1—C14—N7153.6 (2)
C2—N2—C5—C66.0 (3)Cl1—Ni1—C14—N766.1 (2)
C4—N2—C5—C6169.3 (2)C14—N7—C15—C161.6 (3)
N4—N3—C6—C71.4 (2)C13—N7—C15—C16175.6 (2)
Ni2—N3—C6—C7162.60 (17)N7—C15—C16—N80.6 (3)
N4—N3—C6—C5176.6 (2)C14—N8—C16—C150.6 (3)
Ni2—N3—C6—C519.4 (3)C17—N8—C16—C15178.4 (2)
N2—C5—C6—N381.1 (3)C14—N8—C17—C1838.0 (3)
N2—C5—C6—C796.7 (3)C16—N8—C17—C18144.4 (2)
N3—C6—C7—C80.6 (3)N10—N9—C18—C191.4 (3)
C5—C6—C7—C8177.4 (2)Ni1—N9—C18—C19173.75 (16)
N3—N4—C8—C71.4 (3)N10—N9—C18—C17177.6 (2)
Ni1—N4—C8—C7175.06 (16)Ni1—N9—C18—C175.3 (3)
N3—N4—C8—C9178.0 (2)N8—C17—C18—N942.5 (3)
Ni1—N4—C8—C94.3 (3)N8—C17—C18—C19136.3 (2)
C6—C7—C8—N40.5 (3)N9—C18—C19—C200.5 (3)
C6—C7—C8—C9178.9 (2)C17—C18—C19—C20178.4 (2)
C10—N5—C9—C837.5 (3)N9—N10—C20—C191.4 (2)
C11—N5—C9—C8146.6 (2)Ni2—N10—C20—C19160.46 (16)
N4—C8—C9—N542.2 (3)N9—N10—C20—C21173.9 (2)
C7—C8—C9—N5137.1 (3)Ni2—N10—C20—C2124.2 (3)
C11—N5—C10—N61.9 (3)C18—C19—C20—N100.6 (3)
C9—N5—C10—N6178.4 (2)C18—C19—C20—C21174.6 (2)
C11—N5—C10—Ni1170.33 (18)C22—N11—C21—C2025.2 (3)
C9—N5—C10—Ni16.1 (3)C23—N11—C21—C20172.6 (2)
C12—N6—C10—N52.5 (3)N10—C20—C21—N1183.4 (3)
C13—N6—C10—N5178.7 (2)C19—C20—C21—N1191.2 (3)
C12—N6—C10—Ni1169.87 (17)C23—N11—C22—N120.7 (3)
C13—N6—C10—Ni16.3 (3)C21—N11—C22—N12165.59 (19)
C14—Ni1—C10—N5138.8 (2)C24—N12—C22—N110.8 (3)
N4—Ni1—C10—N534.4 (2)C1—N12—C22—N11171.56 (19)
Cl1—Ni1—C10—N5121.6 (2)C22—N11—C23—C240.3 (3)
C14—Ni1—C10—N631.8 (2)C21—N11—C23—C24164.8 (2)
N4—Ni1—C10—N6155.0 (2)N11—C23—C24—N120.2 (3)
Cl1—Ni1—C10—N667.8 (2)C22—N12—C24—C230.6 (3)
C10—N5—C11—C120.7 (3)C1—N12—C24—C23170.9 (2)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···F12ii0.992.393.263 (3)146
C1—H1B···F80.992.363.199 (3)142
C4—H4···F7iii0.952.413.227 (3)144
C5—H5B···N10i0.992.613.407 (3)138
C7—H7···F4iv0.952.523.392 (3)152
C11—H11···F9iv0.952.443.375 (3)168
C13—H13B···F5v0.992.383.356 (3)167
C13—H13B···F6v0.992.473.101 (3)122
C16—H16···N13v0.952.593.186 (3)122
C21—H21A···Cl1i0.992.753.257 (2)112
C21—H21A···N3i0.992.593.376 (3)136
C21—H21B···F3vi0.992.353.238 (3)149
C23—H23···F1vi0.952.503.235 (3)134
C2—H2···N140.91 (3)2.34 (3)3.188 (4)155 (2)
C22—H22···N100.92 (3)2.62 (3)3.156 (3)119 (2)
C26—H26A···F60.982.443.365 (4)157
C28—H28B···F30.982.553.295 (4)133
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x+1, y, z+1; (v) x+1, y, z+2; (vi) x+1, y+1, z+1.
 

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