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The possibility of using less expensive and nontoxic metals, such as copper, as substitutes for more expensive heavy metals in the synthesis of new transition-metal complexes to be used as sensitizers in dye-sensitized solar cells (DSSCs) has stimulated research in this field. The novel photoluminescent cop­per(I) com­plex bis­(tri­phenyl­phosphane-κP)[trans-(±)-2,4,5-tris­(pyridin-2-yl)-2-imidazo­line-κ2N2,N3]copper(I) hexafluorophosphate, [CuI(C18H15N5)(C18H15P)2]PF6, has been successfully synthesized and characterized by IR and 1H NMR spectroscopy, as well as by single-crystal X-ray diffraction and thermogravimetric analysis. The complex showed inter­esting photophysical properties, which were studied experimentally in solution and in the solid state by UV–Vis and fluorescence spectroscopy. Density functional theory (DFT) calculations with di­chloro­methane as solvent reproduced reasonably well the HOMO and LUMO orbitals of the title compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617002522/wq3130sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617002522/wq3130Isup2.hkl
Contains datablock I

CCDC reference: 1532543

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(triphenylphosphane-κP)[trans-(±)-2,4,5-tris(pyridin-2-yl)-2-imidazoline-κ2N2,N3]copper(I) hexafluorophosphate top
Crystal data top
[Cu(C18H15N5)(C18H15P)2]PF6F(000) = 2128
Mr = 1034.40Dx = 1.433 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.0725 (7) ÅCell parameters from 9963 reflections
b = 12.3992 (6) Åθ = 3.2–28.7°
c = 30.0047 (16) ŵ = 0.62 mm1
β = 99.734 (5)°T = 100 K
V = 4793.4 (4) Å3Block, translucent yellow
Z = 40.25 × 0.25 × 0.2 mm
Data collection top
SuperNova, Dual, Cu at zero, EosS2
diffractometer
8448 independent reflections
Radiation source: SuperNova (Mo) X-ray Source6739 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.098
Detector resolution: 8.0769 pixels mm-1θmax = 25.0°, θmin = 2.6°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1414
Tmin = 0.004, Tmax = 1.000l = 3535
29729 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.057P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
8448 reflectionsΔρmax = 0.64 e Å3
616 parametersΔρmin = 1.17 e Å3
0 restraints
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. The single-crystal X-ray diffraction study was carried out on an Agilent Technologies Super Nova diffractometer equipped with a CCD area detector (EosS2) using Mo Kα radiation (λ = 0.71073 Å) from a microfocus X-ray source and an Oxford Instruments Cryojet cooler. Frames were collected at T = 100 K. The measured intensities were reduced to F2 and corrected for absorption using spherical harmonics (CrysAlis PRO; Agilent, 2014). Intensities were corrected for Lorentz and polarization effects. Structure solution, refinement, and data output were performed with the OLEX2 (Dolomanov et al., 2009) program package using SHELXL2014 (Sheldrick, 2015) for the refinement. Non-H atoms were refined anisotropically.

Hydrogen-bonding interactions in the crystal lattice were calculated with the Mercury program package (Macrae et al., 2008). Figures were created with ORTEP (Farrugia, 1999) and Mercury (Macrae et al., 2008).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5407 (3)0.7706 (2)0.61013 (9)0.0135 (7)
C20.6176 (2)0.7035 (2)0.67708 (9)0.0127 (6)
H20.62260.62510.68080.015*
C30.5047 (2)0.7392 (2)0.68150 (9)0.0145 (7)
H30.50760.80010.70250.017*
C40.7041 (3)0.7544 (2)0.70930 (9)0.0173 (5)
C50.7179 (3)0.8659 (2)0.71014 (9)0.0173 (5)
H50.67030.91020.69220.021*
C60.8027 (3)0.9101 (3)0.73792 (10)0.0283 (8)
H60.81380.98430.73860.034*
C70.8705 (3)0.8421 (3)0.76462 (11)0.0321 (9)
H70.92860.86910.78350.039*
C80.8502 (3)0.7325 (3)0.76270 (10)0.0266 (8)
H80.89530.68710.78130.032*
C90.4419 (2)0.6489 (2)0.69710 (9)0.0165 (7)
C100.4036 (3)0.5651 (2)0.66822 (12)0.0323 (9)
H100.41370.56500.63830.039*
C110.3506 (3)0.4821 (3)0.68462 (13)0.0415 (10)
H110.32360.42550.66590.050*
C120.3382 (3)0.4845 (3)0.72900 (12)0.0334 (9)
H120.30370.42890.74110.040*
C130.3778 (3)0.5705 (3)0.75542 (11)0.0319 (9)
H130.36860.57160.78550.038*
C140.5277 (3)0.8039 (2)0.56194 (9)0.0132 (7)
C150.4368 (3)0.8465 (2)0.53832 (9)0.0185 (7)
H150.37960.85740.55250.022*
C160.4324 (3)0.8729 (2)0.49277 (10)0.0200 (7)
H160.37200.90090.47590.024*
C170.5194 (3)0.8567 (2)0.47326 (9)0.0173 (7)
H170.51900.87450.44310.021*
C180.6071 (3)0.8135 (2)0.49923 (9)0.0148 (7)
H180.66540.80260.48580.018*
C190.8504 (2)0.9632 (2)0.61919 (9)0.0136 (6)
C200.7495 (3)1.0029 (2)0.61330 (10)0.0198 (7)
H200.69540.96260.59730.024*
C210.7292 (3)1.1029 (2)0.63128 (10)0.0234 (8)
H210.66161.12910.62720.028*
C220.8091 (3)1.1629 (2)0.65503 (10)0.0239 (8)
H220.79531.22930.66710.029*
C230.9095 (3)1.1244 (2)0.66086 (10)0.0226 (8)
H230.96331.16520.67680.027*
C240.9304 (3)1.0254 (2)0.64311 (9)0.0184 (7)
H240.99831.00010.64720.022*
C250.9056 (2)0.8583 (2)0.54088 (9)0.0142 (6)
C260.8558 (3)0.9423 (2)0.51449 (10)0.0194 (7)
H260.81430.99090.52690.023*
C270.8686 (3)0.9527 (3)0.46964 (10)0.0259 (8)
H270.83451.00790.45210.031*
C280.9308 (3)0.8831 (3)0.45083 (10)0.0276 (8)
H280.93820.89040.42070.033*
C290.9826 (3)0.8015 (2)0.47724 (10)0.0268 (8)
H291.02670.75540.46500.032*
C300.9688 (3)0.7884 (2)0.52183 (10)0.0201 (7)
H301.00220.73220.53900.024*
C310.9923 (3)0.7856 (2)0.63231 (9)0.0138 (7)
C321.0903 (3)0.8207 (2)0.62730 (10)0.0191 (7)
H321.09850.86450.60300.023*
C331.1766 (3)0.7907 (2)0.65861 (11)0.0252 (8)
H331.24250.81370.65510.030*
C341.1642 (3)0.7264 (2)0.69503 (11)0.0244 (8)
H341.22180.70680.71610.029*
C351.0677 (3)0.6915 (2)0.70019 (11)0.0247 (8)
H351.06000.64810.72470.030*
C360.9811 (3)0.7205 (2)0.66907 (10)0.0179 (7)
H360.91570.69650.67270.021*
C370.6357 (2)0.4693 (2)0.58529 (9)0.0127 (6)
C380.5459 (2)0.5102 (2)0.55872 (9)0.0158 (7)
H380.55040.57010.54050.019*
C390.4509 (3)0.4629 (2)0.55929 (9)0.0173 (7)
H390.39210.49000.54090.021*
C400.4423 (3)0.3756 (2)0.58697 (9)0.0158 (7)
H400.37790.34410.58740.019*
C410.5301 (3)0.3351 (2)0.61404 (10)0.0191 (7)
H410.52450.27670.63290.023*
C420.6261 (3)0.3812 (2)0.61321 (10)0.0172 (7)
H420.68470.35330.63140.021*
C430.7830 (2)0.4903 (2)0.52609 (9)0.0124 (6)
C440.7699 (3)0.3833 (2)0.51195 (10)0.0205 (7)
H440.74820.33220.53100.025*
C450.7888 (3)0.3526 (2)0.46974 (10)0.0248 (8)
H450.78060.28080.46090.030*
C460.8196 (3)0.4274 (3)0.44059 (10)0.0256 (8)
H460.83120.40640.41210.031*
C470.8330 (3)0.5340 (2)0.45413 (10)0.0228 (7)
H470.85460.58480.43490.027*
C480.8140 (2)0.5650 (2)0.49662 (10)0.0177 (7)
H480.82210.63690.50540.021*
C490.8566 (2)0.4747 (2)0.62242 (9)0.0136 (6)
C500.9451 (3)0.4282 (2)0.61068 (10)0.0201 (7)
H500.95230.42350.58040.024*
C511.0230 (3)0.3889 (3)0.64409 (11)0.0266 (8)
H511.08160.35730.63590.032*
C521.0146 (3)0.3959 (2)0.68910 (10)0.0237 (8)
H521.06730.36950.71110.028*
C530.9274 (3)0.4424 (2)0.70135 (10)0.0212 (8)
H530.92130.44730.73170.025*
C540.8484 (3)0.4822 (2)0.66836 (9)0.0185 (7)
H540.79010.51380.67680.022*
Cu10.73795 (3)0.71671 (2)0.58958 (2)0.01164 (12)
N10.6278 (2)0.73058 (17)0.62984 (7)0.0133 (6)
N20.4633 (2)0.77549 (18)0.63520 (8)0.0150 (6)
H2A0.40070.79630.62560.018*
N30.7693 (2)0.68814 (19)0.73561 (8)0.0213 (6)
N40.4286 (2)0.6523 (2)0.74022 (8)0.0233 (6)
N50.6124 (2)0.78650 (16)0.54293 (7)0.0118 (5)
P10.87253 (6)0.82966 (5)0.59659 (2)0.01125 (18)
P20.75691 (6)0.53821 (5)0.58069 (2)0.01199 (18)
F10.32492 (15)0.96571 (13)0.61410 (5)0.0263 (5)
F20.38070 (18)0.98443 (15)0.68944 (6)0.0394 (6)
F30.47607 (17)1.05230 (18)0.63983 (7)0.0460 (6)
F40.33648 (16)1.14638 (13)0.60541 (6)0.0302 (5)
F50.24040 (17)1.07849 (15)0.65432 (7)0.0387 (5)
F60.3923 (2)1.16595 (16)0.68074 (7)0.0512 (7)
P30.35805 (7)1.06711 (6)0.64800 (3)0.0209 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0218 (19)0.0103 (13)0.0098 (14)0.0017 (12)0.0061 (13)0.0013 (11)
C20.0152 (17)0.0129 (13)0.0113 (14)0.0014 (12)0.0060 (13)0.0035 (11)
C30.0188 (18)0.0154 (14)0.0104 (14)0.0030 (13)0.0058 (13)0.0007 (11)
C40.0207 (13)0.0238 (10)0.0096 (10)0.0004 (10)0.0086 (10)0.0015 (8)
C50.0207 (13)0.0238 (10)0.0096 (10)0.0004 (10)0.0086 (10)0.0015 (8)
C60.036 (2)0.0329 (18)0.0194 (17)0.0127 (17)0.0152 (16)0.0075 (14)
C70.024 (2)0.056 (2)0.0161 (17)0.0133 (18)0.0035 (16)0.0090 (16)
C80.020 (2)0.048 (2)0.0112 (16)0.0048 (17)0.0007 (15)0.0012 (14)
C90.0133 (17)0.0236 (15)0.0139 (15)0.0051 (13)0.0055 (13)0.0049 (12)
C100.045 (3)0.0285 (18)0.0275 (19)0.0058 (17)0.0185 (18)0.0059 (14)
C110.047 (3)0.0313 (19)0.051 (2)0.0102 (19)0.023 (2)0.0067 (17)
C120.025 (2)0.0326 (19)0.044 (2)0.0032 (16)0.0089 (18)0.0201 (17)
C130.024 (2)0.052 (2)0.0189 (17)0.0040 (18)0.0016 (16)0.0187 (16)
C140.0197 (18)0.0091 (13)0.0106 (14)0.0018 (12)0.0021 (13)0.0013 (11)
C150.0169 (18)0.0220 (15)0.0165 (16)0.0049 (13)0.0027 (14)0.0023 (12)
C160.0189 (19)0.0238 (16)0.0156 (15)0.0052 (14)0.0024 (14)0.0046 (12)
C170.028 (2)0.0152 (14)0.0084 (14)0.0010 (13)0.0016 (14)0.0003 (11)
C180.0222 (19)0.0143 (13)0.0092 (14)0.0054 (13)0.0060 (13)0.0022 (11)
C190.0186 (18)0.0129 (13)0.0101 (14)0.0002 (12)0.0045 (13)0.0033 (11)
C200.0202 (19)0.0162 (14)0.0208 (16)0.0007 (13)0.0026 (14)0.0004 (12)
C210.0218 (19)0.0198 (15)0.0277 (18)0.0084 (14)0.0015 (15)0.0036 (13)
C220.033 (2)0.0138 (15)0.0229 (17)0.0074 (14)0.0001 (16)0.0029 (12)
C230.027 (2)0.0164 (15)0.0207 (16)0.0001 (14)0.0067 (15)0.0020 (12)
C240.0176 (18)0.0176 (15)0.0190 (16)0.0034 (13)0.0003 (14)0.0009 (12)
C250.0155 (17)0.0130 (13)0.0140 (14)0.0072 (12)0.0025 (13)0.0005 (11)
C260.0172 (19)0.0227 (15)0.0178 (16)0.0006 (13)0.0016 (14)0.0042 (12)
C270.022 (2)0.0321 (18)0.0216 (17)0.0070 (15)0.0019 (15)0.0090 (14)
C280.031 (2)0.043 (2)0.0104 (15)0.0157 (17)0.0088 (15)0.0009 (14)
C290.031 (2)0.0276 (17)0.0237 (18)0.0057 (16)0.0112 (16)0.0092 (14)
C300.025 (2)0.0164 (14)0.0198 (16)0.0052 (14)0.0059 (15)0.0011 (12)
C310.0174 (18)0.0088 (13)0.0154 (15)0.0010 (12)0.0037 (13)0.0033 (11)
C320.0184 (18)0.0151 (14)0.0244 (17)0.0009 (13)0.0057 (14)0.0038 (12)
C330.0129 (19)0.0218 (16)0.039 (2)0.0010 (13)0.0010 (16)0.0009 (14)
C340.019 (2)0.0202 (16)0.0303 (19)0.0033 (14)0.0065 (16)0.0012 (13)
C350.026 (2)0.0222 (16)0.0232 (17)0.0001 (15)0.0032 (16)0.0088 (13)
C360.0150 (18)0.0211 (15)0.0182 (16)0.0039 (13)0.0044 (14)0.0020 (12)
C370.0128 (17)0.0138 (13)0.0117 (14)0.0006 (12)0.0027 (12)0.0034 (11)
C380.0205 (19)0.0155 (14)0.0116 (14)0.0026 (13)0.0032 (13)0.0020 (11)
C390.0182 (18)0.0206 (15)0.0119 (14)0.0023 (13)0.0008 (13)0.0024 (12)
C400.0175 (18)0.0169 (14)0.0141 (14)0.0068 (13)0.0057 (13)0.0067 (12)
C410.028 (2)0.0108 (14)0.0193 (16)0.0039 (13)0.0049 (15)0.0010 (12)
C420.0155 (17)0.0143 (14)0.0209 (16)0.0005 (12)0.0004 (14)0.0007 (12)
C430.0102 (16)0.0153 (14)0.0109 (14)0.0028 (12)0.0004 (12)0.0024 (11)
C440.0216 (19)0.0157 (15)0.0240 (17)0.0018 (13)0.0036 (15)0.0001 (12)
C450.026 (2)0.0270 (16)0.0216 (17)0.0032 (15)0.0062 (15)0.0129 (14)
C460.024 (2)0.041 (2)0.0118 (15)0.0016 (16)0.0039 (15)0.0081 (14)
C470.0209 (19)0.0321 (17)0.0171 (16)0.0050 (15)0.0079 (14)0.0003 (13)
C480.0122 (17)0.0223 (15)0.0184 (16)0.0014 (13)0.0018 (14)0.0015 (12)
C490.0158 (17)0.0116 (13)0.0129 (14)0.0029 (12)0.0013 (13)0.0016 (11)
C500.0182 (19)0.0253 (16)0.0176 (16)0.0038 (14)0.0056 (14)0.0016 (12)
C510.0140 (18)0.0384 (18)0.0281 (18)0.0090 (15)0.0054 (15)0.0079 (15)
C520.0155 (19)0.0312 (17)0.0227 (17)0.0004 (15)0.0018 (15)0.0113 (14)
C530.025 (2)0.0224 (15)0.0158 (16)0.0056 (14)0.0016 (15)0.0053 (12)
C540.0218 (19)0.0156 (14)0.0177 (15)0.0023 (13)0.0022 (14)0.0002 (12)
Cu10.0124 (2)0.01264 (19)0.01029 (19)0.00038 (14)0.00297 (16)0.00059 (13)
N10.0170 (15)0.0141 (12)0.0085 (12)0.0000 (10)0.0013 (11)0.0011 (9)
N20.0101 (14)0.0248 (13)0.0112 (12)0.0060 (11)0.0046 (11)0.0075 (10)
N30.0223 (16)0.0300 (14)0.0115 (13)0.0043 (12)0.0026 (12)0.0018 (11)
N40.0175 (16)0.0402 (15)0.0122 (13)0.0026 (13)0.0024 (12)0.0096 (11)
N50.0156 (14)0.0107 (11)0.0099 (12)0.0032 (10)0.0041 (11)0.0026 (9)
P10.0118 (4)0.0117 (3)0.0107 (4)0.0001 (3)0.0031 (3)0.0001 (3)
P20.0137 (4)0.0128 (4)0.0099 (4)0.0003 (3)0.0030 (3)0.0006 (3)
F10.0317 (12)0.0222 (9)0.0235 (10)0.0048 (8)0.0001 (9)0.0017 (7)
F20.0518 (15)0.0451 (11)0.0190 (10)0.0083 (11)0.0010 (10)0.0137 (8)
F30.0190 (12)0.0648 (14)0.0534 (14)0.0035 (11)0.0043 (11)0.0143 (11)
F40.0384 (13)0.0257 (9)0.0273 (10)0.0047 (9)0.0074 (9)0.0101 (8)
F50.0358 (13)0.0454 (12)0.0410 (12)0.0060 (11)0.0236 (10)0.0031 (9)
F60.075 (2)0.0413 (12)0.0340 (12)0.0179 (12)0.0010 (12)0.0124 (10)
P30.0246 (5)0.0239 (4)0.0150 (4)0.0044 (4)0.0059 (4)0.0011 (3)
Geometric parameters (Å, º) top
C1—C141.486 (4)C29—C301.390 (4)
C1—N11.290 (4)C30—H300.9300
C1—N21.360 (4)C31—C321.386 (4)
C2—H20.9800C31—C361.395 (4)
C2—C31.567 (4)C31—P11.825 (3)
C2—C41.498 (4)C32—H320.9300
C2—N11.484 (3)C32—C331.391 (4)
C3—H30.9800C33—H330.9300
C3—C91.509 (4)C33—C341.384 (5)
C3—N21.474 (3)C34—H340.9300
C4—C51.393 (4)C34—C351.367 (5)
C4—N31.340 (4)C35—H350.9300
C5—H50.9300C35—C361.387 (4)
C5—C61.384 (4)C36—H360.9300
C6—H60.9300C37—C381.399 (4)
C6—C71.378 (5)C37—C421.395 (4)
C7—H70.9300C37—P21.826 (3)
C7—C81.384 (5)C38—H380.9300
C8—H80.9300C38—C391.376 (4)
C8—N31.338 (4)C39—H390.9300
C9—C101.391 (4)C39—C401.381 (4)
C9—N41.335 (4)C40—H400.9300
C10—H100.9300C40—C411.383 (4)
C10—C111.378 (5)C41—H410.9300
C11—H110.9300C41—C421.383 (4)
C11—C121.369 (5)C42—H420.9300
C12—H120.9300C43—C441.394 (4)
C12—C131.376 (5)C43—C481.388 (4)
C13—H130.9300C43—P21.828 (3)
C13—N41.335 (4)C44—H440.9300
C14—C151.382 (4)C44—C451.384 (4)
C14—N51.346 (4)C45—H450.9300
C15—H150.9300C45—C461.381 (5)
C15—C161.397 (4)C46—H460.9300
C16—H160.9300C46—C471.385 (4)
C16—C171.379 (5)C47—H470.9300
C17—H170.9300C47—C481.393 (4)
C17—C181.380 (4)C48—H480.9300
C18—H180.9300C49—C501.390 (4)
C18—N51.344 (3)C49—C541.403 (4)
C19—C201.391 (4)C49—P21.826 (3)
C19—C241.396 (4)C50—H500.9300
C19—P11.831 (3)C50—C511.390 (4)
C20—H200.9300C51—H510.9300
C20—C211.396 (4)C51—C521.376 (4)
C21—H210.9300C52—H520.9300
C21—C221.379 (4)C52—C531.382 (5)
C22—H220.9300C53—H530.9300
C22—C231.379 (5)C53—C541.394 (4)
C23—H230.9300C54—H540.9300
C23—C241.383 (4)Cu1—N12.038 (3)
C24—H240.9300Cu1—N52.150 (2)
C25—C261.400 (4)Cu1—P12.2306 (8)
C25—C301.387 (4)Cu1—P22.2479 (8)
C25—P11.831 (3)N2—H2A0.8600
C26—H260.9300F1—P31.6292 (18)
C26—C271.390 (4)F2—P31.6000 (18)
C27—H270.9300F3—P31.613 (2)
C27—C281.371 (5)F4—P31.5990 (17)
C28—H280.9300F5—P31.587 (2)
C28—C291.388 (4)F6—P31.587 (2)
C29—H290.9300
N1—C1—C14120.0 (3)C35—C34—C33120.3 (3)
N1—C1—N2116.4 (2)C35—C34—H34119.8
N2—C1—C14123.5 (3)C34—C35—H35119.8
C3—C2—H2108.5C34—C35—C36120.3 (3)
C4—C2—H2108.5C36—C35—H35119.8
C4—C2—C3116.5 (2)C31—C36—H36120.0
N1—C2—H2108.5C35—C36—C31120.0 (3)
N1—C2—C3104.8 (2)C35—C36—H36120.0
N1—C2—C4109.9 (2)C38—C37—P2116.3 (2)
C2—C3—H3109.7C42—C37—C38118.3 (3)
C9—C3—C2112.7 (2)C42—C37—P2125.4 (2)
C9—C3—H3109.7C37—C38—H38119.7
N2—C3—C2102.0 (2)C39—C38—C37120.7 (3)
N2—C3—H3109.7C39—C38—H38119.7
N2—C3—C9112.8 (2)C38—C39—H39119.8
C5—C4—C2120.7 (3)C38—C39—C40120.5 (3)
N3—C4—C2117.2 (2)C40—C39—H39119.8
N3—C4—C5122.0 (3)C39—C40—H40120.2
C4—C5—H5120.3C39—C40—C41119.6 (3)
C6—C5—C4119.5 (3)C41—C40—H40120.2
C6—C5—H5120.3C40—C41—H41119.8
C5—C6—H6120.7C42—C41—C40120.3 (3)
C7—C6—C5118.6 (3)C42—C41—H41119.8
C7—C6—H6120.7C37—C42—H42119.7
C6—C7—H7120.8C41—C42—C37120.6 (3)
C6—C7—C8118.5 (3)C41—C42—H42119.7
C8—C7—H7120.8C44—C43—P2123.3 (2)
C7—C8—H8118.1C48—C43—C44118.4 (3)
N3—C8—C7123.7 (3)C48—C43—P2118.2 (2)
N3—C8—H8118.1C43—C44—H44119.7
C10—C9—C3121.2 (3)C45—C44—C43120.5 (3)
N4—C9—C3116.3 (3)C45—C44—H44119.7
N4—C9—C10122.4 (3)C44—C45—H45119.6
C9—C10—H10120.5C46—C45—C44120.7 (3)
C11—C10—C9119.0 (3)C46—C45—H45119.6
C11—C10—H10120.5C45—C46—H46120.3
C10—C11—H11120.6C45—C46—C47119.4 (3)
C12—C11—C10118.8 (3)C47—C46—H46120.3
C12—C11—H11120.6C46—C47—H47120.1
C11—C12—H12120.6C46—C47—C48119.9 (3)
C11—C12—C13118.8 (3)C48—C47—H47120.1
C13—C12—H12120.6C43—C48—C47121.0 (3)
C12—C13—H13118.2C43—C48—H48119.5
N4—C13—C12123.6 (3)C47—C48—H48119.5
N4—C13—H13118.2C50—C49—C54118.8 (3)
C15—C14—C1123.5 (3)C50—C49—P2122.2 (2)
N5—C14—C1113.6 (3)C54—C49—P2118.7 (2)
N5—C14—C15122.8 (3)C49—C50—H50119.9
C14—C15—H15120.6C49—C50—C51120.1 (3)
C14—C15—C16118.7 (3)C51—C50—H50119.9
C16—C15—H15120.6C50—C51—H51119.5
C15—C16—H16120.6C52—C51—C50121.0 (3)
C17—C16—C15118.8 (3)C52—C51—H51119.5
C17—C16—H16120.6C51—C52—H52120.2
C16—C17—H17120.6C51—C52—C53119.6 (3)
C16—C17—C18118.9 (3)C53—C52—H52120.2
C18—C17—H17120.6C52—C53—H53119.9
C17—C18—H18118.4C52—C53—C54120.3 (3)
N5—C18—C17123.2 (3)C54—C53—H53119.9
N5—C18—H18118.4C49—C54—H54119.9
C20—C19—C24118.8 (3)C53—C54—C49120.3 (3)
C20—C19—P1118.6 (2)C53—C54—H54119.9
C24—C19—P1122.6 (2)N1—Cu1—N579.26 (9)
C19—C20—H20119.9N1—Cu1—P1121.09 (7)
C19—C20—C21120.3 (3)N1—Cu1—P2104.87 (7)
C21—C20—H20119.9N5—Cu1—P1108.16 (6)
C20—C21—H21120.0N5—Cu1—P2113.97 (6)
C22—C21—C20120.1 (3)P1—Cu1—P2121.89 (3)
C22—C21—H21120.0C1—N1—C2108.1 (3)
C21—C22—H22120.0C1—N1—Cu1114.70 (19)
C21—C22—C23120.1 (3)C2—N1—Cu1137.18 (19)
C23—C22—H22120.0C1—N2—C3108.6 (2)
C22—C23—H23119.9C1—N2—H2A125.7
C22—C23—C24120.2 (3)C3—N2—H2A125.7
C24—C23—H23119.9C8—N3—C4117.6 (3)
C19—C24—H24119.7C9—N4—C13117.4 (3)
C23—C24—C19120.6 (3)C14—N5—Cu1112.38 (17)
C23—C24—H24119.7C18—N5—C14117.6 (3)
C26—C25—P1120.1 (2)C18—N5—Cu1130.0 (2)
C30—C25—C26119.0 (3)C19—P1—Cu1115.57 (11)
C30—C25—P1120.3 (2)C25—P1—C19103.81 (13)
C25—C26—H26120.1C25—P1—Cu1109.87 (9)
C27—C26—C25119.7 (3)C31—P1—C19103.10 (12)
C27—C26—H26120.1C31—P1—C25106.44 (14)
C26—C27—H27119.4C31—P1—Cu1116.88 (9)
C28—C27—C26121.1 (3)C37—P2—C43102.20 (13)
C28—C27—H27119.4C37—P2—C49105.90 (13)
C27—C28—H28120.3C37—P2—Cu1109.73 (9)
C27—C28—C29119.3 (3)C43—P2—Cu1117.87 (9)
C29—C28—H28120.3C49—P2—C43104.74 (13)
C28—C29—H29119.8C49—P2—Cu1115.06 (9)
C28—C29—C30120.3 (3)F2—P3—F189.17 (10)
C30—C29—H29119.8F2—P3—F389.38 (12)
C25—C30—C29120.4 (3)F3—P3—F188.70 (12)
C25—C30—H30119.8F4—P3—F189.02 (9)
C29—C30—H30119.8F4—P3—F2177.93 (12)
C32—C31—C36119.4 (3)F4—P3—F389.57 (12)
C32—C31—P1124.0 (2)F5—P3—F188.99 (11)
C36—C31—P1116.3 (2)F5—P3—F291.14 (12)
C31—C32—H32119.9F5—P3—F3177.62 (12)
C31—C32—C33120.1 (3)F5—P3—F489.84 (11)
C33—C32—H32119.9F6—P3—F1178.97 (15)
C32—C33—H33120.1F6—P3—F291.03 (11)
C34—C33—C32119.9 (3)F6—P3—F390.30 (14)
C34—C33—H33120.1F6—P3—F490.76 (11)
C33—C34—H34119.8F6—P3—F592.01 (14)
C1—C14—C15—C16178.6 (2)C34—C35—C36—C310.0 (5)
C1—C14—N5—C18179.4 (2)C36—C31—C32—C330.3 (4)
C1—C14—N5—Cu10.3 (3)C36—C31—P1—C1995.7 (2)
C2—C3—C9—C1073.9 (4)C36—C31—P1—C25155.4 (2)
C2—C3—C9—N4103.9 (3)C36—C31—P1—Cu132.3 (2)
C2—C3—N2—C14.5 (3)C37—C38—C39—C401.5 (4)
C2—C4—C5—C6175.4 (3)C38—C37—C42—C410.8 (4)
C2—C4—N3—C8176.4 (3)C38—C37—P2—C4375.5 (2)
C3—C2—C4—C559.7 (4)C38—C37—P2—C49175.1 (2)
C3—C2—C4—N3122.9 (3)C38—C37—P2—Cu150.4 (2)
C3—C2—N1—C11.3 (3)C38—C39—C40—C410.4 (4)
C3—C2—N1—Cu1178.93 (19)C39—C40—C41—C420.5 (4)
C3—C9—C10—C11177.2 (3)C40—C41—C42—C370.3 (5)
C3—C9—N4—C13176.7 (3)C42—C37—C38—C391.7 (4)
C4—C2—C3—C9113.7 (3)C42—C37—P2—C43105.4 (3)
C4—C2—C3—N2125.1 (2)C42—C37—P2—C494.0 (3)
C4—C2—N1—C1127.2 (2)C42—C37—P2—Cu1128.8 (2)
C4—C2—N1—Cu155.2 (3)C43—C44—C45—C460.9 (5)
C4—C5—C6—C71.1 (5)C44—C43—C48—C470.9 (4)
C5—C4—N3—C81.0 (5)C44—C43—P2—C3742.4 (3)
C5—C6—C7—C80.5 (5)C44—C43—P2—C4967.9 (3)
C6—C7—C8—N31.5 (5)C44—C43—P2—Cu1162.7 (2)
C7—C8—N3—C40.7 (5)C44—C45—C46—C470.9 (5)
C9—C3—N2—C1125.7 (3)C45—C46—C47—C480.9 (5)
C9—C10—C11—C120.7 (6)C46—C47—C48—C430.9 (5)
C10—C9—N4—C131.0 (5)C48—C43—C44—C450.9 (5)
C10—C11—C12—C131.0 (6)C48—C43—P2—C37135.2 (2)
C11—C12—C13—N40.4 (6)C48—C43—P2—C49114.5 (2)
C12—C13—N4—C90.6 (5)C48—C43—P2—Cu114.9 (3)
C14—C1—N1—C2179.2 (2)C49—C50—C51—C520.6 (5)
C14—C1—N1—Cu11.0 (3)C50—C49—C54—C530.8 (4)
C14—C1—N2—C3178.4 (2)C50—C49—P2—C37123.5 (2)
C14—C15—C16—C170.8 (4)C50—C49—P2—C4315.9 (3)
C15—C14—N5—C180.8 (4)C50—C49—P2—Cu1115.1 (2)
C15—C14—N5—Cu1178.9 (2)C50—C51—C52—C530.2 (5)
C15—C16—C17—C180.9 (4)C51—C52—C53—C540.1 (5)
C16—C17—C18—N50.2 (4)C52—C53—C54—C490.4 (4)
C17—C18—N5—C140.7 (4)C54—C49—C50—C510.9 (4)
C17—C18—N5—Cu1179.00 (19)C54—C49—P2—C3762.8 (2)
C19—C20—C21—C220.1 (5)C54—C49—P2—C43170.4 (2)
C20—C19—C24—C230.4 (4)C54—C49—P2—Cu158.6 (2)
C20—C19—P1—C2594.5 (3)N1—C1—C14—C15179.4 (3)
C20—C19—P1—C31154.7 (2)N1—C1—C14—N50.8 (4)
C20—C19—P1—Cu125.9 (3)N1—C1—N2—C34.3 (3)
C20—C21—C22—C230.4 (5)N1—C2—C3—C9124.6 (2)
C21—C22—C23—C240.3 (5)N1—C2—C3—N23.5 (3)
C22—C23—C24—C190.1 (5)N1—C2—C4—C559.2 (4)
C24—C19—C20—C210.3 (5)N1—C2—C4—N3118.2 (3)
C24—C19—P1—C2587.3 (3)N2—C1—C14—C152.2 (4)
C24—C19—P1—C3123.5 (3)N2—C1—C14—N5176.4 (2)
C24—C19—P1—Cu1152.3 (2)N2—C1—N1—C21.8 (3)
C25—C26—C27—C281.1 (5)N2—C1—N1—Cu1176.45 (18)
C26—C25—C30—C290.1 (4)N2—C3—C9—C1040.9 (4)
C26—C25—P1—C1937.0 (3)N2—C3—C9—N4141.3 (3)
C26—C25—P1—C31145.5 (2)N3—C4—C5—C61.9 (5)
C26—C25—P1—Cu187.1 (2)N4—C9—C10—C110.4 (5)
C26—C27—C28—C290.7 (5)N5—C14—C15—C160.1 (4)
C27—C28—C29—C302.1 (5)P1—C19—C20—C21178.0 (2)
C28—C29—C30—C251.8 (5)P1—C19—C24—C23177.8 (2)
C30—C25—C26—C271.4 (4)P1—C25—C26—C27169.7 (2)
C30—C25—P1—C19152.0 (2)P1—C25—C30—C29171.1 (2)
C30—C25—P1—C3143.6 (3)P1—C31—C32—C33174.1 (2)
C30—C25—P1—Cu183.8 (2)P1—C31—C36—C35174.2 (2)
C31—C32—C33—C340.6 (5)P2—C37—C38—C39179.1 (2)
C32—C31—C36—C350.0 (4)P2—C37—C42—C41180.0 (2)
C32—C31—P1—C1978.3 (3)P2—C43—C44—C45178.5 (2)
C32—C31—P1—C2530.7 (3)P2—C43—C48—C47178.7 (2)
C32—C31—P1—Cu1153.8 (2)P2—C49—C50—C51174.6 (2)
C32—C33—C34—C350.6 (5)P2—C49—C54—C53174.7 (2)
C33—C34—C35—C360.2 (5)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C9–C13/N4 ring and Cg2 is the centroid of the C43–C48 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···F5i0.932.483.339 (4)153
C15—H15···F10.932.493.259 (4)141
C17—H17···F4ii0.932.593.260 (4)130
C17—H17···F3ii0.932.663.586 (4)174
C27—H27···F1ii0.932.653.404 (4)139
C33—H33···F1iii0.932.583.336 (4)138
C34—H34···Cg1iii0.932.823.517133
C39—H39···Cg2iv0.932.593.467 (4)158
C40—H40···F4v0.932.593.249 (3)129
N2—H2A···F10.862.322.975 (3)133
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x+1, y+2, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x, y1, z.
 

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