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Although there are many examples of acetate complexes, acetamide complexes are virtually unknown. A side-by-side comparison in (acetato-[kappa]2O,O')(1,4,7,10-tetra­methyl-1,4,7,10-tetra­aza­cyclo­dodecane-[kappa]4N)nickel(II) hexafluoridophosphate, [Ni(C2H3O2)(C12H28N4)]PF6, (1), and (acetamidato-[kappa]2O,O')(1,4,7,10-tetra­methyl-1,4,7,10-tetra­aza­cyclo­dodecane-[kappa]4N)nickel(II) hexafluoridophosphate, [Ni(C2H4NO)(C12H28N4)]PF6, (2), shows the steric equivalence between these two ligands, suggesting that acetamide could be considered as a viable acetate replacement for electronic tuning.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614011620/sf3230sup1.cif
Contains datablocks 1, 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614011620/sf32301sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614011620/sf32302sup3.hkl
Contains datablock 2

CCDC references: 1004252; 1004253

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: APEX2 (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(1) (Acetato-κ2O,O')(1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane-κ4N)nickel(II) hexafluoridophosphate top
Crystal data top
[Ni(C2H3O2)(C12H28N4)]PF6F(000) = 1024
Mr = 491.11Dx = 1.548 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 10.5588 (10) ÅCell parameters from 2513 reflections
b = 11.7643 (11) Åθ = 2.4–20.9°
c = 17.2263 (16) ŵ = 1.07 mm1
β = 99.929 (2)°T = 200 K
V = 2107.7 (3) Å3Needle, blue
Z = 40.20 × 0.12 × 0.12 mm
Data collection top
Bruker APEXII
diffractometer
4725 independent reflections
Graphite monochromator4117 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1Rint = 0.041
φ and ω scansθmax = 27.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1313
Tmin = 0.642, Tmax = 0.746k = 1515
11775 measured reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0446P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.52 e Å3
4725 reflectionsΔρmin = 0.30 e Å3
259 parametersAbsolute structure: Refined as an inversion twin
2 restraintsAbsolute structure parameter: 0.143 (19)
0 constraints
Special details top

Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames), at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 ° (600 frames). Frame width = 0.30 \& in ω.

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. Refined as a two-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50415 (4)0.57477 (4)0.24742 (3)0.02109 (15)
O10.6177 (3)0.4425 (3)0.3014 (2)0.0310 (8)
O20.4145 (4)0.4484 (3)0.3095 (2)0.0317 (8)
N10.3346 (4)0.6648 (4)0.2049 (2)0.0285 (10)
N20.4746 (4)0.5075 (3)0.1290 (2)0.0282 (10)
N30.6602 (4)0.6608 (3)0.2126 (2)0.0274 (9)
N40.5284 (4)0.6994 (4)0.3399 (2)0.0286 (9)
C10.3311 (6)0.6791 (5)0.1191 (3)0.0417 (14)
H1A0.39450.73740.11000.050*
H1B0.24470.70540.09390.050*
C20.3618 (6)0.5673 (5)0.0828 (4)0.0430 (15)
H2A0.28570.51700.07810.052*
H2B0.37890.58180.02890.052*
C30.5945 (6)0.5355 (5)0.0997 (3)0.0378 (13)
H3A0.57830.53170.04140.045*
H3B0.66090.47810.11950.045*
C40.6452 (6)0.6529 (5)0.1254 (3)0.0345 (12)
H4A0.72910.66570.10860.041*
H4B0.58440.71180.10060.041*
C50.6534 (6)0.7792 (5)0.2404 (4)0.0340 (14)
H5A0.58200.81970.20680.041*
H5B0.73460.81930.23680.041*
C60.6316 (6)0.7784 (5)0.3253 (3)0.0375 (13)
H6A0.71280.75680.35990.045*
H6B0.60930.85630.33990.045*
C70.4016 (6)0.7575 (5)0.3324 (4)0.0431 (15)
H7A0.41310.83220.35920.052*
H7B0.34310.71140.35880.052*
C80.3416 (6)0.7747 (5)0.2467 (4)0.0377 (15)
H8A0.25420.80690.24330.045*
H8B0.39390.82900.22180.045*
C90.2194 (6)0.6009 (6)0.2195 (4)0.0402 (15)
H9A0.22330.59120.27640.060*
H9B0.21750.52600.19430.060*
H9C0.14150.64320.19750.060*
C100.4539 (6)0.3836 (5)0.1231 (4)0.0411 (14)
H10A0.44710.35990.06800.062*
H10B0.37430.36420.14210.062*
H10C0.52640.34450.15530.062*
C110.7841 (5)0.6101 (6)0.2487 (4)0.0375 (14)
H11A0.85470.65730.23670.056*
H11B0.79120.53350.22740.056*
H11C0.78880.60560.30590.056*
C120.5620 (6)0.6527 (6)0.4200 (3)0.0431 (15)
H12A0.57180.71500.45840.065*
H12B0.64300.61050.42480.065*
H12C0.49370.60140.43030.065*
C130.5251 (5)0.4019 (5)0.3285 (3)0.0286 (11)
C140.5438 (6)0.3008 (5)0.3817 (3)0.0407 (14)
H14A0.55280.23250.35050.061*
H14B0.46930.29240.40810.061*
H14C0.62160.31120.42120.061*
P10.45346 (14)0.01522 (13)0.51715 (9)0.0344 (3)
F10.4883 (5)0.0116 (4)0.4309 (3)0.0858 (15)
F20.3829 (4)0.1338 (4)0.4933 (3)0.0717 (12)
F30.5792 (4)0.0863 (3)0.5493 (3)0.0792 (15)
F40.4172 (6)0.0244 (4)0.6019 (3)0.0963 (18)
F50.5291 (5)0.0987 (4)0.5378 (4)0.100 (2)
F60.3272 (4)0.0550 (4)0.4857 (3)0.0704 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0217 (3)0.0185 (3)0.0234 (3)0.0004 (3)0.0049 (2)0.0002 (3)
O10.028 (2)0.027 (2)0.039 (2)0.0045 (15)0.0076 (16)0.0086 (16)
O20.028 (2)0.028 (2)0.040 (2)0.0015 (15)0.0070 (16)0.0055 (16)
N10.027 (2)0.024 (2)0.033 (2)0.0022 (18)0.0025 (18)0.0003 (17)
N20.031 (2)0.027 (2)0.028 (2)0.0043 (19)0.0069 (18)0.0023 (18)
N30.027 (2)0.024 (2)0.032 (2)0.0032 (18)0.0075 (18)0.0010 (18)
N40.028 (2)0.031 (2)0.028 (2)0.0009 (19)0.0075 (17)0.0062 (18)
C10.043 (4)0.040 (3)0.038 (3)0.005 (3)0.007 (3)0.009 (3)
C20.042 (4)0.056 (4)0.029 (3)0.001 (3)0.001 (2)0.002 (3)
C30.043 (3)0.040 (3)0.035 (3)0.012 (3)0.020 (3)0.012 (2)
C40.042 (3)0.036 (3)0.028 (3)0.010 (3)0.014 (2)0.000 (2)
C50.036 (3)0.018 (3)0.048 (4)0.007 (2)0.009 (3)0.003 (3)
C60.042 (3)0.034 (3)0.037 (3)0.010 (3)0.009 (2)0.015 (2)
C70.037 (3)0.042 (3)0.051 (4)0.009 (3)0.011 (3)0.020 (3)
C80.035 (4)0.025 (3)0.053 (4)0.010 (3)0.007 (3)0.002 (3)
C90.027 (3)0.037 (3)0.056 (4)0.004 (3)0.007 (3)0.001 (3)
C100.053 (4)0.032 (3)0.041 (3)0.017 (3)0.017 (3)0.011 (3)
C110.020 (3)0.037 (3)0.056 (4)0.003 (3)0.008 (3)0.001 (3)
C120.057 (4)0.048 (4)0.023 (3)0.005 (3)0.003 (3)0.005 (2)
C130.032 (3)0.027 (3)0.027 (3)0.003 (2)0.003 (2)0.002 (2)
C140.051 (4)0.031 (3)0.039 (3)0.001 (3)0.005 (3)0.016 (3)
P10.0307 (7)0.0369 (8)0.0338 (8)0.0035 (7)0.0003 (6)0.0098 (6)
F10.119 (4)0.082 (4)0.067 (3)0.024 (3)0.045 (3)0.027 (3)
F20.079 (3)0.055 (3)0.076 (3)0.017 (2)0.000 (2)0.006 (2)
F30.055 (3)0.056 (3)0.117 (4)0.008 (2)0.013 (3)0.035 (3)
F40.160 (5)0.091 (3)0.049 (3)0.036 (4)0.048 (3)0.018 (2)
F50.102 (4)0.043 (2)0.132 (5)0.030 (3)0.047 (3)0.023 (3)
F60.047 (2)0.081 (3)0.081 (3)0.023 (2)0.005 (2)0.018 (2)
Geometric parameters (Å, º) top
Ni1—N12.100 (4)C5—H5A0.9900
Ni1—N22.160 (4)C5—H5B0.9900
Ni1—N32.107 (4)C6—H6A0.9900
Ni1—N42.148 (4)C6—H6B0.9900
Ni1—O12.083 (3)C7—C81.517 (9)
Ni1—O22.145 (4)C7—H7A0.9900
Ni1—C132.456 (6)C7—H7B0.9900
O1—C131.250 (7)C8—H8A0.9900
O2—C131.280 (7)C8—H8B0.9900
N1—C81.477 (7)C9—H9A0.9800
N1—C11.480 (7)C9—H9B0.9800
N1—C91.488 (8)C9—H9C0.9800
N2—C101.475 (7)C10—H10A0.9800
N2—C31.479 (6)C10—H10B0.9800
N2—C21.490 (7)C10—H10C0.9800
N3—C111.475 (7)C11—H11A0.9800
N3—C51.478 (7)C11—H11B0.9800
N3—C41.486 (6)C11—H11C0.9800
N4—C121.471 (7)C12—H12A0.9800
N4—C61.486 (7)C12—H12B0.9800
N4—C71.488 (7)C12—H12C0.9800
C1—C21.516 (8)C13—C141.493 (7)
C1—H1A0.9900C14—H14A0.9800
C1—H1B0.9900C14—H14B0.9800
C2—H2A0.9900C14—H14C0.9800
C2—H2B0.9900P1—F51.570 (4)
C3—C41.519 (8)P1—F41.576 (4)
C3—H3A0.9900P1—F61.582 (4)
C3—H3B0.9900P1—F31.586 (4)
C4—H4A0.9900P1—F11.592 (5)
C4—H4B0.9900P1—F21.602 (4)
C5—C61.519 (8)
O1—Ni1—N1157.34 (15)C6—C5—H5A109.8
O1—Ni1—N393.89 (15)N3—C5—H5B109.8
N1—Ni1—N3108.64 (17)C6—C5—H5B109.8
O1—Ni1—O261.92 (14)H5A—C5—H5B108.3
N1—Ni1—O295.77 (16)N4—C6—C5113.9 (4)
N3—Ni1—O2155.39 (15)N4—C6—H6A108.8
O1—Ni1—N4101.13 (16)C5—C6—H6A108.8
N1—Ni1—N484.28 (16)N4—C6—H6B108.8
N3—Ni1—N483.35 (16)C5—C6—H6B108.8
O2—Ni1—N496.30 (16)H6A—C6—H6B107.7
O1—Ni1—N297.25 (16)N4—C7—C8111.4 (4)
N1—Ni1—N283.07 (16)N4—C7—H7A109.4
N3—Ni1—N284.25 (16)C8—C7—H7A109.4
O2—Ni1—N2102.28 (15)N4—C7—H7B109.4
N4—Ni1—N2158.44 (16)C8—C7—H7B109.4
O1—Ni1—C1330.58 (16)H7A—C7—H7B108.0
N1—Ni1—C13127.13 (18)N1—C8—C7109.6 (5)
N3—Ni1—C13124.20 (18)N1—C8—H8A109.7
O2—Ni1—C1331.38 (16)C7—C8—H8A109.7
N4—Ni1—C1398.97 (17)N1—C8—H8B109.7
N2—Ni1—C13102.59 (17)C7—C8—H8B109.7
C13—O1—Ni191.4 (3)H8A—C8—H8B108.2
C13—O2—Ni187.8 (3)N1—C9—H9A109.5
C8—N1—C1112.2 (4)N1—C9—H9B109.5
C8—N1—C9109.5 (4)H9A—C9—H9B109.5
C1—N1—C9110.3 (4)N1—C9—H9C109.5
C8—N1—Ni1107.6 (3)H9A—C9—H9C109.5
C1—N1—Ni1106.2 (3)H9B—C9—H9C109.5
C9—N1—Ni1111.0 (3)N2—C10—H10A109.5
C10—N2—C3108.8 (4)N2—C10—H10B109.5
C10—N2—C2109.5 (4)H10A—C10—H10B109.5
C3—N2—C2111.4 (5)N2—C10—H10C109.5
C10—N2—Ni1115.0 (3)H10A—C10—H10C109.5
C3—N2—Ni1104.3 (3)H10B—C10—H10C109.5
C2—N2—Ni1107.7 (3)N3—C11—H11A109.5
C11—N3—C5109.5 (5)N3—C11—H11B109.5
C11—N3—C4109.5 (4)H11A—C11—H11B109.5
C5—N3—C4112.6 (4)N3—C11—H11C109.5
C11—N3—Ni1111.5 (3)H11A—C11—H11C109.5
C5—N3—Ni1106.1 (3)H11B—C11—H11C109.5
C4—N3—Ni1107.8 (3)N4—C12—H12A109.5
C12—N4—C6109.1 (4)N4—C12—H12B109.5
C12—N4—C7108.7 (4)H12A—C12—H12B109.5
C6—N4—C7111.9 (4)N4—C12—H12C109.5
C12—N4—Ni1114.8 (3)H12A—C12—H12C109.5
C6—N4—Ni1107.3 (3)H12B—C12—H12C109.5
C7—N4—Ni1105.0 (3)O1—C13—O2118.7 (5)
N1—C1—C2110.0 (4)O1—C13—C14120.3 (5)
N1—C1—H1A109.7O2—C13—C14121.0 (5)
C2—C1—H1A109.7O1—C13—Ni158.0 (3)
N1—C1—H1B109.7O2—C13—Ni160.8 (3)
C2—C1—H1B109.7C14—C13—Ni1176.3 (4)
H1A—C1—H1B108.2C13—C14—H14A109.5
N2—C2—C1113.4 (5)C13—C14—H14B109.5
N2—C2—H2A108.9H14A—C14—H14B109.5
C1—C2—H2A108.9C13—C14—H14C109.5
N2—C2—H2B108.9H14A—C14—H14C109.5
C1—C2—H2B108.9H14B—C14—H14C109.5
H2A—C2—H2B107.7F5—P1—F492.5 (3)
N2—C3—C4112.5 (4)F5—P1—F689.9 (3)
N2—C3—H3A109.1F4—P1—F691.6 (3)
C4—C3—H3A109.1F5—P1—F390.5 (3)
N2—C3—H3B109.1F4—P1—F387.8 (3)
C4—C3—H3B109.1F6—P1—F3179.4 (3)
H3A—C3—H3B107.8F5—P1—F189.9 (3)
N3—C4—C3108.8 (4)F4—P1—F1177.5 (3)
N3—C4—H4A109.9F6—P1—F189.0 (3)
C3—C4—H4A109.9F3—P1—F191.5 (3)
N3—C4—H4B109.9F5—P1—F2176.6 (3)
C3—C4—H4B109.9F4—P1—F290.1 (3)
H4A—C4—H4B108.3F6—P1—F292.3 (2)
N3—C5—C6109.3 (4)F3—P1—F287.4 (3)
N3—C5—H5A109.8F1—P1—F287.5 (3)
C8—N1—C1—C2164.0 (5)Ni1—N3—C5—C646.5 (5)
C9—N1—C1—C273.7 (6)C12—N4—C6—C5146.5 (5)
Ni1—N1—C1—C246.7 (5)C7—N4—C6—C593.1 (6)
C10—N2—C2—C1145.6 (5)Ni1—N4—C6—C521.5 (6)
C3—N2—C2—C194.0 (6)N3—C5—C6—N446.9 (6)
Ni1—N2—C2—C119.9 (6)C12—N4—C7—C8162.1 (5)
N1—C1—C2—N245.6 (7)C6—N4—C7—C877.3 (6)
C10—N2—C3—C4162.9 (5)Ni1—N4—C7—C838.7 (5)
C2—N2—C3—C476.2 (6)C1—N1—C8—C7155.5 (5)
Ni1—N2—C3—C439.7 (5)C9—N1—C8—C781.7 (6)
C11—N3—C4—C382.9 (6)Ni1—N1—C8—C739.1 (5)
C5—N3—C4—C3155.1 (5)N4—C7—C8—N154.2 (6)
Ni1—N3—C4—C338.5 (5)Ni1—O1—C13—O24.1 (5)
N2—C3—C4—N354.7 (6)Ni1—O1—C13—C14176.2 (5)
C11—N3—C5—C673.8 (6)Ni1—O2—C13—O14.0 (5)
C4—N3—C5—C6164.2 (4)Ni1—O2—C13—C14176.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···F2i0.992.503.202 (7)127
C1—H1B···F5ii0.992.633.389 (8)133
C2—H2A···F3ii0.992.473.451 (8)170
C4—H4B···F3i0.992.533.362 (7)141
C5—H5B···O2iii0.992.583.442 (7)146
C7—H7A···F1iv0.992.503.480 (8)169
C8—H8A···O1v0.992.473.337 (7)146
C12—H12B···F2iii0.982.623.412 (7)138
C14—H14B···F20.982.633.402 (7)136
Symmetry codes: (i) x, y+1, z1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z; (iv) x, y+1, z; (v) x1/2, y+1/2, z.
(2) (Acetamidato-κ2O,O')(1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane-κ4N)nickel(II) hexafluoridophosphate top
Crystal data top
[Ni(C2H4NO)(C12H28N4)]PF6Z = 2
Mr = 490.12F(000) = 512
Triclinic, P1Dx = 1.541 Mg m3
a = 8.0392 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.6289 (10) ÅCell parameters from 4379 reflections
c = 15.8882 (19) Åθ = 2.5–21.9°
α = 78.883 (2)°µ = 1.06 mm1
β = 89.641 (2)°T = 200 K
γ = 77.826 (2)°Plate, blue
V = 1056.5 (2) Å30.49 × 0.34 × 0.07 mm
Data collection top
Bruker APEXII
diffractometer
3720 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1Rint = 0.064
φ and ω scansθmax = 27.8°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1010
Tmin = 0.592, Tmax = 0.746k = 1111
26793 measured reflectionsl = 2020
4810 independent reflections
Refinement top
Refinement on F27 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0317P)2 + 0.7758P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4810 reflectionsΔρmax = 0.80 e Å3
271 parametersΔρmin = 0.56 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.35609 (4)0.45003 (4)0.23694 (2)0.02149 (10)
N10.1327 (3)0.3770 (2)0.20368 (13)0.0270 (5)
N20.1810 (3)0.6008 (2)0.30687 (14)0.0305 (5)
N30.4362 (3)0.3191 (3)0.36320 (14)0.0305 (5)
N40.4822 (3)0.2269 (3)0.20044 (14)0.0300 (5)
N50.3676 (3)0.6179 (3)0.12767 (14)0.0309 (5)
H5N0.324 (4)0.669 (3)0.0827 (19)0.037*
O10.5728 (2)0.5622 (2)0.22545 (11)0.0326 (4)
C10.0044 (3)0.4356 (3)0.25969 (19)0.0355 (6)
H1A0.00600.35960.31560.043*
H1B0.11680.44150.23270.043*
C20.0091 (3)0.6015 (3)0.2734 (2)0.0383 (7)
H2A0.01570.67980.21820.046*
H2B0.07690.63710.31440.046*
C30.2052 (4)0.5275 (4)0.40008 (18)0.0437 (7)
H3A0.09310.54210.42710.052*
H3B0.27710.58520.42750.052*
C40.2877 (4)0.3487 (4)0.41657 (17)0.0398 (7)
H4A0.32360.31130.47790.048*
H4B0.20410.28660.40330.048*
C50.4942 (4)0.1463 (3)0.35932 (18)0.0385 (7)
H5A0.39510.09460.36110.046*
H5B0.57130.09040.40930.046*
C60.5869 (4)0.1323 (3)0.27709 (19)0.0434 (7)
H6A0.69390.17130.27930.052*
H6B0.61740.01720.27210.052*
C70.3485 (4)0.1458 (3)0.17720 (19)0.0378 (7)
H7A0.38820.02750.19610.045*
H7B0.33260.16870.11390.045*
C80.1782 (3)0.1982 (3)0.21629 (19)0.0340 (6)
H8A0.08920.15900.18880.041*
H8B0.18480.15060.27840.041*
C90.0800 (4)0.4469 (4)0.11289 (18)0.0398 (7)
H9A0.01380.40110.09650.060*
H9B0.17650.42140.07630.060*
H9C0.04230.56440.10570.060*
C100.2029 (4)0.7709 (3)0.2921 (2)0.0451 (8)
H10A0.18890.81770.23060.068*
H10B0.31700.77300.31250.068*
H10C0.11720.83400.32340.068*
C110.5788 (4)0.3768 (4)0.39645 (18)0.0432 (7)
H11A0.54610.49400.39270.065*
H11B0.67910.35140.36220.065*
H11C0.60570.32320.45650.065*
C120.5965 (4)0.2496 (4)0.1273 (2)0.0442 (7)
H12A0.68380.30470.14210.066*
H12B0.52980.31500.07650.066*
H12C0.65130.14390.11510.066*
C130.5097 (3)0.6448 (3)0.15271 (16)0.0268 (5)
C140.6060 (4)0.7611 (3)0.10163 (18)0.0383 (7)
H14A0.65820.81390.14060.057*
H14B0.52730.84300.06080.057*
H14C0.69500.70200.07030.057*
P10.00000.00000.00000.0250 (2)
P20.00000.00000.50000.0295 (2)
F10.1916 (2)0.0034 (2)0.02653 (12)0.0510 (5)
F20.0553 (2)0.18309 (19)0.01107 (11)0.0525 (5)
F30.0372 (2)0.0592 (2)0.09804 (10)0.0501 (5)
F50.1877 (2)0.0281 (2)0.46488 (12)0.0550 (5)
F40.0669 (4)0.0535 (5)0.40314 (17)0.0837 (13)0.768 (4)
F60.0068 (5)0.1836 (3)0.5021 (3)0.0833 (13)0.768 (4)
F4'0.0555 (14)0.1423 (17)0.4245 (6)0.0837 (13)0.232 (4)
F6'0.0794 (14)0.1083 (13)0.5479 (8)0.0833 (13)0.232 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01885 (16)0.02385 (17)0.02261 (17)0.00717 (12)0.00068 (12)0.00373 (12)
N10.0232 (11)0.0270 (11)0.0322 (12)0.0101 (9)0.0006 (9)0.0037 (9)
N20.0333 (12)0.0274 (11)0.0316 (12)0.0066 (10)0.0054 (10)0.0079 (9)
N30.0281 (12)0.0336 (12)0.0291 (12)0.0086 (10)0.0011 (9)0.0020 (9)
N40.0272 (12)0.0290 (11)0.0353 (12)0.0064 (9)0.0052 (10)0.0100 (10)
N50.0275 (12)0.0351 (13)0.0290 (12)0.0118 (10)0.0022 (10)0.0023 (10)
O10.0242 (9)0.0384 (10)0.0353 (10)0.0124 (8)0.0029 (8)0.0009 (8)
C10.0188 (13)0.0413 (16)0.0465 (17)0.0086 (12)0.0040 (12)0.0070 (13)
C20.0260 (14)0.0366 (15)0.0503 (18)0.0010 (12)0.0071 (13)0.0095 (13)
C30.0502 (19)0.0506 (18)0.0285 (15)0.0040 (15)0.0099 (13)0.0114 (13)
C40.0428 (17)0.0485 (18)0.0246 (14)0.0089 (14)0.0041 (12)0.0007 (12)
C50.0384 (16)0.0322 (15)0.0379 (16)0.0026 (13)0.0065 (13)0.0048 (12)
C60.0386 (17)0.0353 (16)0.0503 (19)0.0054 (13)0.0024 (14)0.0087 (14)
C70.0397 (16)0.0309 (14)0.0490 (18)0.0128 (13)0.0052 (14)0.0173 (13)
C80.0324 (15)0.0288 (14)0.0443 (16)0.0143 (12)0.0005 (12)0.0067 (12)
C90.0372 (16)0.0476 (17)0.0369 (16)0.0196 (14)0.0113 (13)0.0016 (13)
C100.0541 (19)0.0306 (15)0.0554 (19)0.0114 (14)0.0117 (15)0.0180 (14)
C110.0416 (18)0.0558 (19)0.0330 (16)0.0165 (15)0.0119 (13)0.0039 (14)
C120.0420 (18)0.0470 (17)0.0488 (18)0.0112 (14)0.0224 (14)0.0213 (15)
C130.0236 (13)0.0255 (13)0.0319 (14)0.0063 (10)0.0055 (11)0.0060 (11)
C140.0342 (16)0.0371 (15)0.0440 (17)0.0157 (13)0.0084 (13)0.0005 (13)
P10.0247 (5)0.0230 (4)0.0275 (5)0.0072 (4)0.0016 (4)0.0029 (4)
P20.0267 (5)0.0293 (5)0.0290 (5)0.0038 (4)0.0048 (4)0.0002 (4)
F10.0301 (9)0.0613 (12)0.0611 (12)0.0167 (8)0.0103 (8)0.0023 (9)
F20.0700 (13)0.0269 (8)0.0594 (12)0.0036 (8)0.0076 (10)0.0127 (8)
F30.0555 (11)0.0592 (11)0.0308 (9)0.0113 (9)0.0046 (8)0.0021 (8)
F50.0328 (10)0.0643 (12)0.0615 (12)0.0037 (9)0.0178 (8)0.0046 (10)
F40.0581 (15)0.142 (4)0.0265 (14)0.036 (2)0.0048 (12)0.0184 (16)
F60.080 (2)0.0326 (17)0.148 (4)0.0216 (15)0.072 (2)0.0359 (19)
F4'0.0581 (15)0.142 (4)0.0265 (14)0.036 (2)0.0048 (12)0.0184 (16)
F6'0.080 (2)0.0326 (17)0.148 (4)0.0216 (15)0.072 (2)0.0359 (19)
Geometric parameters (Å, º) top
Ni1—N12.126 (2)C1—C21.514 (4)
Ni1—N22.162 (2)C3—C41.518 (4)
Ni1—N32.133 (2)C5—C61.513 (4)
Ni1—N42.162 (2)C7—C81.517 (4)
Ni1—O12.1550 (17)C13—C141.506 (3)
Ni1—N52.051 (2)P1—F31.5901 (16)
N5—C131.293 (3)P1—F3i1.5901 (16)
O1—C131.280 (3)P1—F2i1.5920 (15)
Ni1—C132.476 (2)P1—F21.5920 (15)
N1—C91.479 (3)P1—F11.5921 (16)
N1—C11.480 (3)P1—F1i1.5921 (16)
N1—C81.482 (3)P2—F4'ii1.534 (10)
N2—C21.483 (3)P2—F4'1.534 (10)
N2—C101.488 (3)P2—F6'1.546 (9)
N2—C31.491 (3)P2—F6'ii1.546 (9)
N3—C41.467 (3)P2—F6ii1.581 (2)
N3—C51.478 (3)P2—F61.581 (2)
N3—C111.480 (3)P2—F41.582 (3)
N4—C61.482 (3)P2—F4ii1.582 (3)
N4—C71.484 (3)P2—F51.5921 (16)
N4—C121.486 (3)P2—F5ii1.5921 (16)
N5—Ni1—N198.45 (8)N4—C7—C8113.8 (2)
N5—Ni1—N3154.59 (9)N1—C8—C7109.8 (2)
N1—Ni1—N3106.87 (8)O1—C13—N5116.3 (2)
N5—Ni1—O162.55 (8)O1—C13—C14118.9 (2)
N1—Ni1—O1160.58 (7)N5—C13—C14124.8 (2)
N3—Ni1—O192.31 (7)O1—C13—Ni160.47 (12)
N5—Ni1—N4102.31 (9)N5—C13—Ni155.83 (13)
N1—Ni1—N482.96 (8)C14—C13—Ni1179.01 (19)
N3—Ni1—N483.10 (8)F3—P1—F3i180.0
O1—Ni1—N496.65 (8)F3—P1—F2i90.02 (9)
N5—Ni1—N298.93 (9)F3i—P1—F2i89.98 (9)
N1—Ni1—N283.27 (8)F3—P1—F289.98 (9)
N3—Ni1—N282.37 (8)F3i—P1—F290.02 (9)
O1—Ni1—N2102.76 (8)F2i—P1—F2180.0
N4—Ni1—N2156.13 (8)F3—P1—F189.76 (9)
N5—Ni1—C1331.43 (8)F3i—P1—F190.24 (9)
N1—Ni1—C13129.80 (8)F2i—P1—F189.70 (10)
N3—Ni1—C13123.32 (8)F2—P1—F190.30 (10)
O1—Ni1—C1331.12 (7)F3—P1—F1i90.24 (9)
N4—Ni1—C13101.36 (8)F3i—P1—F1i89.76 (9)
N2—Ni1—C13102.44 (8)F2i—P1—F1i90.30 (10)
C9—N1—C1109.4 (2)F2—P1—F1i89.70 (10)
C9—N1—C8109.8 (2)F1—P1—F1i180.0
C1—N1—C8112.9 (2)F4'ii—P2—F4'180.0
C9—N1—Ni1110.52 (15)F4'ii—P2—F6'89.6 (6)
C1—N1—Ni1108.13 (15)F4'—P2—F6'90.4 (6)
C8—N1—Ni1106.11 (15)F4'ii—P2—F6'ii90.4 (6)
C2—N2—C10108.1 (2)F4'—P2—F6'ii89.6 (6)
C2—N2—C3111.9 (2)F6'—P2—F6'ii180.0
C10—N2—C3109.9 (2)F6ii—P2—F6180.0
C2—N2—Ni1105.25 (15)F6ii—P2—F491.32 (19)
C10—N2—Ni1113.30 (17)F6—P2—F488.68 (19)
C3—N2—Ni1108.34 (16)F6ii—P2—F4ii88.68 (19)
C4—N3—C5112.6 (2)F6—P2—F4ii91.32 (19)
C4—N3—C11110.1 (2)F4—P2—F4ii180.0 (3)
C5—N3—C11108.9 (2)F4'ii—P2—F590.6 (4)
C4—N3—Ni1106.05 (16)F4'—P2—F589.4 (4)
C5—N3—Ni1108.28 (16)F6'—P2—F579.6 (4)
C11—N3—Ni1110.87 (16)F6'ii—P2—F5100.4 (4)
C6—N4—C7112.4 (2)F6ii—P2—F586.56 (12)
C6—N4—C12108.4 (2)F6—P2—F593.44 (12)
C7—N4—C12109.2 (2)F4—P2—F587.30 (13)
C6—N4—Ni1105.33 (16)F4ii—P2—F592.70 (13)
C7—N4—Ni1107.69 (15)F4'ii—P2—F5ii89.4 (4)
C12—N4—Ni1113.80 (16)F4'—P2—F5ii90.6 (4)
C13—N5—Ni192.74 (16)F6'—P2—F5ii100.4 (4)
C13—O1—Ni188.41 (14)F6'ii—P2—F5ii79.6 (4)
N1—C1—C2109.4 (2)F6ii—P2—F5ii93.44 (12)
N2—C2—C1111.5 (2)F6—P2—F5ii86.56 (12)
N2—C3—C4112.8 (2)F4—P2—F5ii92.70 (13)
N3—C4—C3110.4 (2)F4ii—P2—F5ii87.30 (13)
N3—C5—C6109.2 (2)F5—P2—F5ii180.0
N4—C6—C5112.0 (2)
C9—N1—C1—C282.4 (3)Ni1—N3—C5—C637.7 (3)
C8—N1—C1—C2155.0 (2)C7—N4—C6—C576.7 (3)
Ni1—N1—C1—C238.0 (2)C12—N4—C6—C5162.5 (2)
C10—N2—C2—C1162.0 (2)Ni1—N4—C6—C540.3 (3)
C3—N2—C2—C176.9 (3)N3—C5—C6—N454.2 (3)
Ni1—N2—C2—C140.6 (3)C6—N4—C7—C893.1 (3)
N1—C1—C2—N254.6 (3)C12—N4—C7—C8146.5 (2)
C2—N2—C3—C494.1 (3)Ni1—N4—C7—C822.5 (3)
C10—N2—C3—C4145.8 (3)C9—N1—C8—C773.7 (3)
Ni1—N2—C3—C421.5 (3)C1—N1—C8—C7164.0 (2)
C5—N3—C4—C3165.0 (2)Ni1—N1—C8—C745.7 (2)
C11—N3—C4—C373.2 (3)N4—C7—C8—N147.1 (3)
Ni1—N3—C4—C346.8 (3)Ni1—O1—C13—N50.9 (2)
N2—C3—C4—N347.1 (3)Ni1—O1—C13—C14179.1 (2)
C4—N3—C5—C6154.6 (2)Ni1—N5—C13—O10.9 (2)
C11—N3—C5—C682.9 (3)Ni1—N5—C13—C14179.0 (2)
Symmetry codes: (i) x, y, z; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···F2iii0.80 (3)2.58 (3)3.302 (3)150 (3)
C1—H1A···F40.992.433.362 (12)158
C1—H1B···O1iv0.992.493.357 (3)146
C2—H2A···F3v0.992.633.589 (3)162
C4—H4B···F60.992.493.181 (4)127
C4—H4B···F40.992.643.576 (16)159
C5—H5A···F50.992.583.419 (3)143
C7—H7B···F10.992.643.301 (3)125
C9—H9A···F20.982.603.386 (3)138
C9—H9C···F2iii0.982.603.380 (3)137
C10—H10C···F6vi0.982.643.557 (10)157
C11—H11B···F4vii0.982.553.177 (10)122
Symmetry codes: (iii) x, y+1, z; (iv) x1, y, z; (v) x, y+1, z; (vi) x, y+1, z+1; (vii) x+1, y, z.
 

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