Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617002522/wq3130sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617002522/wq3130Isup2.hkl |
CCDC reference: 1532543
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).
[Cu(C18H15N5)(C18H15P)2]PF6 | F(000) = 2128 |
Mr = 1034.40 | Dx = 1.433 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0725 (7) Å | Cell parameters from 9963 reflections |
b = 12.3992 (6) Å | θ = 3.2–28.7° |
c = 30.0047 (16) Å | µ = 0.62 mm−1 |
β = 99.734 (5)° | T = 100 K |
V = 4793.4 (4) Å3 | Block, translucent yellow |
Z = 4 | 0.25 × 0.25 × 0.2 mm |
SuperNova, Dual, Cu at zero, EosS2 diffractometer | 8448 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 6739 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.098 |
Detector resolution: 8.0769 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −14→14 |
Tmin = 0.004, Tmax = 1.000 | l = −35→35 |
29729 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.64 e Å−3 |
616 parameters | Δρmin = −1.17 e Å−3 |
0 restraints |
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). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5407 (3) | 0.7706 (2) | 0.61013 (9) | 0.0135 (7) | |
C2 | 0.6176 (2) | 0.7035 (2) | 0.67708 (9) | 0.0127 (6) | |
H2 | 0.6226 | 0.6251 | 0.6808 | 0.015* | |
C3 | 0.5047 (2) | 0.7392 (2) | 0.68150 (9) | 0.0145 (7) | |
H3 | 0.5076 | 0.8001 | 0.7025 | 0.017* | |
C4 | 0.7041 (3) | 0.7544 (2) | 0.70930 (9) | 0.0173 (5) | |
C5 | 0.7179 (3) | 0.8659 (2) | 0.71014 (9) | 0.0173 (5) | |
H5 | 0.6703 | 0.9102 | 0.6922 | 0.021* | |
C6 | 0.8027 (3) | 0.9101 (3) | 0.73792 (10) | 0.0283 (8) | |
H6 | 0.8138 | 0.9843 | 0.7386 | 0.034* | |
C7 | 0.8705 (3) | 0.8421 (3) | 0.76462 (11) | 0.0321 (9) | |
H7 | 0.9286 | 0.8691 | 0.7835 | 0.039* | |
C8 | 0.8502 (3) | 0.7325 (3) | 0.76270 (10) | 0.0266 (8) | |
H8 | 0.8953 | 0.6871 | 0.7813 | 0.032* | |
C9 | 0.4419 (2) | 0.6489 (2) | 0.69710 (9) | 0.0165 (7) | |
C10 | 0.4036 (3) | 0.5651 (2) | 0.66822 (12) | 0.0323 (9) | |
H10 | 0.4137 | 0.5650 | 0.6383 | 0.039* | |
C11 | 0.3506 (3) | 0.4821 (3) | 0.68462 (13) | 0.0415 (10) | |
H11 | 0.3236 | 0.4255 | 0.6659 | 0.050* | |
C12 | 0.3382 (3) | 0.4845 (3) | 0.72900 (12) | 0.0334 (9) | |
H12 | 0.3037 | 0.4289 | 0.7411 | 0.040* | |
C13 | 0.3778 (3) | 0.5705 (3) | 0.75542 (11) | 0.0319 (9) | |
H13 | 0.3686 | 0.5716 | 0.7855 | 0.038* | |
C14 | 0.5277 (3) | 0.8039 (2) | 0.56194 (9) | 0.0132 (7) | |
C15 | 0.4368 (3) | 0.8465 (2) | 0.53832 (9) | 0.0185 (7) | |
H15 | 0.3796 | 0.8574 | 0.5525 | 0.022* | |
C16 | 0.4324 (3) | 0.8729 (2) | 0.49277 (10) | 0.0200 (7) | |
H16 | 0.3720 | 0.9009 | 0.4759 | 0.024* | |
C17 | 0.5194 (3) | 0.8567 (2) | 0.47326 (9) | 0.0173 (7) | |
H17 | 0.5190 | 0.8745 | 0.4431 | 0.021* | |
C18 | 0.6071 (3) | 0.8135 (2) | 0.49923 (9) | 0.0148 (7) | |
H18 | 0.6654 | 0.8026 | 0.4858 | 0.018* | |
C19 | 0.8504 (2) | 0.9632 (2) | 0.61919 (9) | 0.0136 (6) | |
C20 | 0.7495 (3) | 1.0029 (2) | 0.61330 (10) | 0.0198 (7) | |
H20 | 0.6954 | 0.9626 | 0.5973 | 0.024* | |
C21 | 0.7292 (3) | 1.1029 (2) | 0.63128 (10) | 0.0234 (8) | |
H21 | 0.6616 | 1.1291 | 0.6272 | 0.028* | |
C22 | 0.8091 (3) | 1.1629 (2) | 0.65503 (10) | 0.0239 (8) | |
H22 | 0.7953 | 1.2293 | 0.6671 | 0.029* | |
C23 | 0.9095 (3) | 1.1244 (2) | 0.66086 (10) | 0.0226 (8) | |
H23 | 0.9633 | 1.1652 | 0.6768 | 0.027* | |
C24 | 0.9304 (3) | 1.0254 (2) | 0.64311 (9) | 0.0184 (7) | |
H24 | 0.9983 | 1.0001 | 0.6472 | 0.022* | |
C25 | 0.9056 (2) | 0.8583 (2) | 0.54088 (9) | 0.0142 (6) | |
C26 | 0.8558 (3) | 0.9423 (2) | 0.51449 (10) | 0.0194 (7) | |
H26 | 0.8143 | 0.9909 | 0.5269 | 0.023* | |
C27 | 0.8686 (3) | 0.9527 (3) | 0.46964 (10) | 0.0259 (8) | |
H27 | 0.8345 | 1.0079 | 0.4521 | 0.031* | |
C28 | 0.9308 (3) | 0.8831 (3) | 0.45083 (10) | 0.0276 (8) | |
H28 | 0.9382 | 0.8904 | 0.4207 | 0.033* | |
C29 | 0.9826 (3) | 0.8015 (2) | 0.47724 (10) | 0.0268 (8) | |
H29 | 1.0267 | 0.7554 | 0.4650 | 0.032* | |
C30 | 0.9688 (3) | 0.7884 (2) | 0.52183 (10) | 0.0201 (7) | |
H30 | 1.0022 | 0.7322 | 0.5390 | 0.024* | |
C31 | 0.9923 (3) | 0.7856 (2) | 0.63231 (9) | 0.0138 (7) | |
C32 | 1.0903 (3) | 0.8207 (2) | 0.62730 (10) | 0.0191 (7) | |
H32 | 1.0985 | 0.8645 | 0.6030 | 0.023* | |
C33 | 1.1766 (3) | 0.7907 (2) | 0.65861 (11) | 0.0252 (8) | |
H33 | 1.2425 | 0.8137 | 0.6551 | 0.030* | |
C34 | 1.1642 (3) | 0.7264 (2) | 0.69503 (11) | 0.0244 (8) | |
H34 | 1.2218 | 0.7068 | 0.7161 | 0.029* | |
C35 | 1.0677 (3) | 0.6915 (2) | 0.70019 (11) | 0.0247 (8) | |
H35 | 1.0600 | 0.6481 | 0.7247 | 0.030* | |
C36 | 0.9811 (3) | 0.7205 (2) | 0.66907 (10) | 0.0179 (7) | |
H36 | 0.9157 | 0.6965 | 0.6727 | 0.021* | |
C37 | 0.6357 (2) | 0.4693 (2) | 0.58529 (9) | 0.0127 (6) | |
C38 | 0.5459 (2) | 0.5102 (2) | 0.55872 (9) | 0.0158 (7) | |
H38 | 0.5504 | 0.5701 | 0.5405 | 0.019* | |
C39 | 0.4509 (3) | 0.4629 (2) | 0.55929 (9) | 0.0173 (7) | |
H39 | 0.3921 | 0.4900 | 0.5409 | 0.021* | |
C40 | 0.4423 (3) | 0.3756 (2) | 0.58697 (9) | 0.0158 (7) | |
H40 | 0.3779 | 0.3441 | 0.5874 | 0.019* | |
C41 | 0.5301 (3) | 0.3351 (2) | 0.61404 (10) | 0.0191 (7) | |
H41 | 0.5245 | 0.2767 | 0.6329 | 0.023* | |
C42 | 0.6261 (3) | 0.3812 (2) | 0.61321 (10) | 0.0172 (7) | |
H42 | 0.6847 | 0.3533 | 0.6314 | 0.021* | |
C43 | 0.7830 (2) | 0.4903 (2) | 0.52609 (9) | 0.0124 (6) | |
C44 | 0.7699 (3) | 0.3833 (2) | 0.51195 (10) | 0.0205 (7) | |
H44 | 0.7482 | 0.3322 | 0.5310 | 0.025* | |
C45 | 0.7888 (3) | 0.3526 (2) | 0.46974 (10) | 0.0248 (8) | |
H45 | 0.7806 | 0.2808 | 0.4609 | 0.030* | |
C46 | 0.8196 (3) | 0.4274 (3) | 0.44059 (10) | 0.0256 (8) | |
H46 | 0.8312 | 0.4064 | 0.4121 | 0.031* | |
C47 | 0.8330 (3) | 0.5340 (2) | 0.45413 (10) | 0.0228 (7) | |
H47 | 0.8546 | 0.5848 | 0.4349 | 0.027* | |
C48 | 0.8140 (2) | 0.5650 (2) | 0.49662 (10) | 0.0177 (7) | |
H48 | 0.8221 | 0.6369 | 0.5054 | 0.021* | |
C49 | 0.8566 (2) | 0.4747 (2) | 0.62242 (9) | 0.0136 (6) | |
C50 | 0.9451 (3) | 0.4282 (2) | 0.61068 (10) | 0.0201 (7) | |
H50 | 0.9523 | 0.4235 | 0.5804 | 0.024* | |
C51 | 1.0230 (3) | 0.3889 (3) | 0.64409 (11) | 0.0266 (8) | |
H51 | 1.0816 | 0.3573 | 0.6359 | 0.032* | |
C52 | 1.0146 (3) | 0.3959 (2) | 0.68910 (10) | 0.0237 (8) | |
H52 | 1.0673 | 0.3695 | 0.7111 | 0.028* | |
C53 | 0.9274 (3) | 0.4424 (2) | 0.70135 (10) | 0.0212 (8) | |
H53 | 0.9213 | 0.4473 | 0.7317 | 0.025* | |
C54 | 0.8484 (3) | 0.4822 (2) | 0.66836 (9) | 0.0185 (7) | |
H54 | 0.7901 | 0.5138 | 0.6768 | 0.022* | |
Cu1 | 0.73795 (3) | 0.71671 (2) | 0.58958 (2) | 0.01164 (12) | |
N1 | 0.6278 (2) | 0.73058 (17) | 0.62984 (7) | 0.0133 (6) | |
N2 | 0.4633 (2) | 0.77549 (18) | 0.63520 (8) | 0.0150 (6) | |
H2A | 0.4007 | 0.7963 | 0.6256 | 0.018* | |
N3 | 0.7693 (2) | 0.68814 (19) | 0.73561 (8) | 0.0213 (6) | |
N4 | 0.4286 (2) | 0.6523 (2) | 0.74022 (8) | 0.0233 (6) | |
N5 | 0.6124 (2) | 0.78650 (16) | 0.54293 (7) | 0.0118 (5) | |
P1 | 0.87253 (6) | 0.82966 (5) | 0.59659 (2) | 0.01125 (18) | |
P2 | 0.75691 (6) | 0.53821 (5) | 0.58069 (2) | 0.01199 (18) | |
F1 | 0.32492 (15) | 0.96571 (13) | 0.61410 (5) | 0.0263 (5) | |
F2 | 0.38070 (18) | 0.98443 (15) | 0.68944 (6) | 0.0394 (6) | |
F3 | 0.47607 (17) | 1.05230 (18) | 0.63983 (7) | 0.0460 (6) | |
F4 | 0.33648 (16) | 1.14638 (13) | 0.60541 (6) | 0.0302 (5) | |
F5 | 0.24040 (17) | 1.07849 (15) | 0.65432 (7) | 0.0387 (5) | |
F6 | 0.3923 (2) | 1.16595 (16) | 0.68074 (7) | 0.0512 (7) | |
P3 | 0.35805 (7) | 1.06711 (6) | 0.64800 (3) | 0.0209 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0218 (19) | 0.0103 (13) | 0.0098 (14) | −0.0017 (12) | 0.0061 (13) | −0.0013 (11) |
C2 | 0.0152 (17) | 0.0129 (13) | 0.0113 (14) | 0.0014 (12) | 0.0060 (13) | 0.0035 (11) |
C3 | 0.0188 (18) | 0.0154 (14) | 0.0104 (14) | 0.0030 (13) | 0.0058 (13) | 0.0007 (11) |
C4 | 0.0207 (13) | 0.0238 (10) | 0.0096 (10) | −0.0004 (10) | 0.0086 (10) | −0.0015 (8) |
C5 | 0.0207 (13) | 0.0238 (10) | 0.0096 (10) | −0.0004 (10) | 0.0086 (10) | −0.0015 (8) |
C6 | 0.036 (2) | 0.0329 (18) | 0.0194 (17) | −0.0127 (17) | 0.0152 (16) | −0.0075 (14) |
C7 | 0.024 (2) | 0.056 (2) | 0.0161 (17) | −0.0133 (18) | 0.0035 (16) | −0.0090 (16) |
C8 | 0.020 (2) | 0.048 (2) | 0.0112 (16) | 0.0048 (17) | −0.0007 (15) | −0.0012 (14) |
C9 | 0.0133 (17) | 0.0236 (15) | 0.0139 (15) | 0.0051 (13) | 0.0055 (13) | 0.0049 (12) |
C10 | 0.045 (3) | 0.0285 (18) | 0.0275 (19) | −0.0058 (17) | 0.0185 (18) | −0.0059 (14) |
C11 | 0.047 (3) | 0.0313 (19) | 0.051 (2) | −0.0102 (19) | 0.023 (2) | −0.0067 (17) |
C12 | 0.025 (2) | 0.0326 (19) | 0.044 (2) | −0.0032 (16) | 0.0089 (18) | 0.0201 (17) |
C13 | 0.024 (2) | 0.052 (2) | 0.0189 (17) | −0.0040 (18) | 0.0016 (16) | 0.0187 (16) |
C14 | 0.0197 (18) | 0.0091 (13) | 0.0106 (14) | −0.0018 (12) | 0.0021 (13) | −0.0013 (11) |
C15 | 0.0169 (18) | 0.0220 (15) | 0.0165 (16) | 0.0049 (13) | 0.0027 (14) | −0.0023 (12) |
C16 | 0.0189 (19) | 0.0238 (16) | 0.0156 (15) | 0.0052 (14) | −0.0024 (14) | 0.0046 (12) |
C17 | 0.028 (2) | 0.0152 (14) | 0.0084 (14) | −0.0010 (13) | 0.0016 (14) | −0.0003 (11) |
C18 | 0.0222 (19) | 0.0143 (13) | 0.0092 (14) | −0.0054 (13) | 0.0060 (13) | −0.0022 (11) |
C19 | 0.0186 (18) | 0.0129 (13) | 0.0101 (14) | 0.0002 (12) | 0.0045 (13) | 0.0033 (11) |
C20 | 0.0202 (19) | 0.0162 (14) | 0.0208 (16) | −0.0007 (13) | −0.0026 (14) | −0.0004 (12) |
C21 | 0.0218 (19) | 0.0198 (15) | 0.0277 (18) | 0.0084 (14) | 0.0015 (15) | −0.0036 (13) |
C22 | 0.033 (2) | 0.0138 (15) | 0.0229 (17) | 0.0074 (14) | 0.0001 (16) | −0.0029 (12) |
C23 | 0.027 (2) | 0.0164 (15) | 0.0207 (16) | 0.0001 (14) | −0.0067 (15) | −0.0020 (12) |
C24 | 0.0176 (18) | 0.0176 (15) | 0.0190 (16) | 0.0034 (13) | −0.0003 (14) | −0.0009 (12) |
C25 | 0.0155 (17) | 0.0130 (13) | 0.0140 (14) | −0.0072 (12) | 0.0025 (13) | 0.0005 (11) |
C26 | 0.0172 (19) | 0.0227 (15) | 0.0178 (16) | −0.0006 (13) | 0.0016 (14) | 0.0042 (12) |
C27 | 0.022 (2) | 0.0321 (18) | 0.0216 (17) | −0.0070 (15) | −0.0019 (15) | 0.0090 (14) |
C28 | 0.031 (2) | 0.043 (2) | 0.0104 (15) | −0.0157 (17) | 0.0088 (15) | 0.0009 (14) |
C29 | 0.031 (2) | 0.0276 (17) | 0.0237 (18) | −0.0057 (16) | 0.0112 (16) | −0.0092 (14) |
C30 | 0.025 (2) | 0.0164 (14) | 0.0198 (16) | −0.0052 (14) | 0.0059 (15) | −0.0011 (12) |
C31 | 0.0174 (18) | 0.0088 (13) | 0.0154 (15) | −0.0010 (12) | 0.0037 (13) | −0.0033 (11) |
C32 | 0.0184 (18) | 0.0151 (14) | 0.0244 (17) | −0.0009 (13) | 0.0057 (14) | 0.0038 (12) |
C33 | 0.0129 (19) | 0.0218 (16) | 0.039 (2) | −0.0010 (13) | −0.0010 (16) | 0.0009 (14) |
C34 | 0.019 (2) | 0.0202 (16) | 0.0303 (19) | 0.0033 (14) | −0.0065 (16) | 0.0012 (13) |
C35 | 0.026 (2) | 0.0222 (16) | 0.0232 (17) | −0.0001 (15) | −0.0032 (16) | 0.0088 (13) |
C36 | 0.0150 (18) | 0.0211 (15) | 0.0182 (16) | −0.0039 (13) | 0.0044 (14) | 0.0020 (12) |
C37 | 0.0128 (17) | 0.0138 (13) | 0.0117 (14) | 0.0006 (12) | 0.0027 (12) | −0.0034 (11) |
C38 | 0.0205 (19) | 0.0155 (14) | 0.0116 (14) | −0.0026 (13) | 0.0032 (13) | −0.0020 (11) |
C39 | 0.0182 (18) | 0.0206 (15) | 0.0119 (14) | −0.0023 (13) | −0.0008 (13) | −0.0024 (12) |
C40 | 0.0175 (18) | 0.0169 (14) | 0.0141 (14) | −0.0068 (13) | 0.0057 (13) | −0.0067 (12) |
C41 | 0.028 (2) | 0.0108 (14) | 0.0193 (16) | −0.0039 (13) | 0.0049 (15) | 0.0010 (12) |
C42 | 0.0155 (17) | 0.0143 (14) | 0.0209 (16) | −0.0005 (12) | 0.0004 (14) | −0.0007 (12) |
C43 | 0.0102 (16) | 0.0153 (14) | 0.0109 (14) | 0.0028 (12) | −0.0004 (12) | −0.0024 (11) |
C44 | 0.0216 (19) | 0.0157 (15) | 0.0240 (17) | 0.0018 (13) | 0.0036 (15) | 0.0001 (12) |
C45 | 0.026 (2) | 0.0270 (16) | 0.0216 (17) | 0.0032 (15) | 0.0062 (15) | −0.0129 (14) |
C46 | 0.024 (2) | 0.041 (2) | 0.0118 (15) | 0.0016 (16) | 0.0039 (15) | −0.0081 (14) |
C47 | 0.0209 (19) | 0.0321 (17) | 0.0171 (16) | −0.0050 (15) | 0.0079 (14) | −0.0003 (13) |
C48 | 0.0122 (17) | 0.0223 (15) | 0.0184 (16) | −0.0014 (13) | 0.0018 (14) | −0.0015 (12) |
C49 | 0.0158 (17) | 0.0116 (13) | 0.0129 (14) | −0.0029 (12) | 0.0013 (13) | 0.0016 (11) |
C50 | 0.0182 (19) | 0.0253 (16) | 0.0176 (16) | 0.0038 (14) | 0.0056 (14) | 0.0016 (12) |
C51 | 0.0140 (18) | 0.0384 (18) | 0.0281 (18) | 0.0090 (15) | 0.0054 (15) | 0.0079 (15) |
C52 | 0.0155 (19) | 0.0312 (17) | 0.0227 (17) | −0.0004 (15) | −0.0018 (15) | 0.0113 (14) |
C53 | 0.025 (2) | 0.0224 (15) | 0.0158 (16) | −0.0056 (14) | 0.0016 (15) | 0.0053 (12) |
C54 | 0.0218 (19) | 0.0156 (14) | 0.0177 (15) | −0.0023 (13) | 0.0022 (14) | −0.0002 (12) |
Cu1 | 0.0124 (2) | 0.01264 (19) | 0.01029 (19) | −0.00038 (14) | 0.00297 (16) | −0.00059 (13) |
N1 | 0.0170 (15) | 0.0141 (12) | 0.0085 (12) | 0.0000 (10) | 0.0013 (11) | −0.0011 (9) |
N2 | 0.0101 (14) | 0.0248 (13) | 0.0112 (12) | 0.0060 (11) | 0.0046 (11) | 0.0075 (10) |
N3 | 0.0223 (16) | 0.0300 (14) | 0.0115 (13) | 0.0043 (12) | 0.0026 (12) | 0.0018 (11) |
N4 | 0.0175 (16) | 0.0402 (15) | 0.0122 (13) | −0.0026 (13) | 0.0024 (12) | 0.0096 (11) |
N5 | 0.0156 (14) | 0.0107 (11) | 0.0099 (12) | −0.0032 (10) | 0.0041 (11) | −0.0026 (9) |
P1 | 0.0118 (4) | 0.0117 (3) | 0.0107 (4) | −0.0001 (3) | 0.0031 (3) | −0.0001 (3) |
P2 | 0.0137 (4) | 0.0128 (4) | 0.0099 (4) | −0.0003 (3) | 0.0030 (3) | −0.0006 (3) |
F1 | 0.0317 (12) | 0.0222 (9) | 0.0235 (10) | 0.0048 (8) | 0.0001 (9) | −0.0017 (7) |
F2 | 0.0518 (15) | 0.0451 (11) | 0.0190 (10) | −0.0083 (11) | −0.0010 (10) | 0.0137 (8) |
F3 | 0.0190 (12) | 0.0648 (14) | 0.0534 (14) | −0.0035 (11) | 0.0043 (11) | 0.0143 (11) |
F4 | 0.0384 (13) | 0.0257 (9) | 0.0273 (10) | −0.0047 (9) | 0.0074 (9) | 0.0101 (8) |
F5 | 0.0358 (13) | 0.0454 (12) | 0.0410 (12) | 0.0060 (11) | 0.0236 (10) | 0.0031 (9) |
F6 | 0.075 (2) | 0.0413 (12) | 0.0340 (12) | −0.0179 (12) | −0.0010 (12) | −0.0124 (10) |
P3 | 0.0246 (5) | 0.0239 (4) | 0.0150 (4) | −0.0044 (4) | 0.0059 (4) | 0.0011 (3) |
C1—C14 | 1.486 (4) | C29—C30 | 1.390 (4) |
C1—N1 | 1.290 (4) | C30—H30 | 0.9300 |
C1—N2 | 1.360 (4) | C31—C32 | 1.386 (4) |
C2—H2 | 0.9800 | C31—C36 | 1.395 (4) |
C2—C3 | 1.567 (4) | C31—P1 | 1.825 (3) |
C2—C4 | 1.498 (4) | C32—H32 | 0.9300 |
C2—N1 | 1.484 (3) | C32—C33 | 1.391 (4) |
C3—H3 | 0.9800 | C33—H33 | 0.9300 |
C3—C9 | 1.509 (4) | C33—C34 | 1.384 (5) |
C3—N2 | 1.474 (3) | C34—H34 | 0.9300 |
C4—C5 | 1.393 (4) | C34—C35 | 1.367 (5) |
C4—N3 | 1.340 (4) | C35—H35 | 0.9300 |
C5—H5 | 0.9300 | C35—C36 | 1.387 (4) |
C5—C6 | 1.384 (4) | C36—H36 | 0.9300 |
C6—H6 | 0.9300 | C37—C38 | 1.399 (4) |
C6—C7 | 1.378 (5) | C37—C42 | 1.395 (4) |
C7—H7 | 0.9300 | C37—P2 | 1.826 (3) |
C7—C8 | 1.384 (5) | C38—H38 | 0.9300 |
C8—H8 | 0.9300 | C38—C39 | 1.376 (4) |
C8—N3 | 1.338 (4) | C39—H39 | 0.9300 |
C9—C10 | 1.391 (4) | C39—C40 | 1.381 (4) |
C9—N4 | 1.335 (4) | C40—H40 | 0.9300 |
C10—H10 | 0.9300 | C40—C41 | 1.383 (4) |
C10—C11 | 1.378 (5) | C41—H41 | 0.9300 |
C11—H11 | 0.9300 | C41—C42 | 1.383 (4) |
C11—C12 | 1.369 (5) | C42—H42 | 0.9300 |
C12—H12 | 0.9300 | C43—C44 | 1.394 (4) |
C12—C13 | 1.376 (5) | C43—C48 | 1.388 (4) |
C13—H13 | 0.9300 | C43—P2 | 1.828 (3) |
C13—N4 | 1.335 (4) | C44—H44 | 0.9300 |
C14—C15 | 1.382 (4) | C44—C45 | 1.384 (4) |
C14—N5 | 1.346 (4) | C45—H45 | 0.9300 |
C15—H15 | 0.9300 | C45—C46 | 1.381 (5) |
C15—C16 | 1.397 (4) | C46—H46 | 0.9300 |
C16—H16 | 0.9300 | C46—C47 | 1.385 (4) |
C16—C17 | 1.379 (5) | C47—H47 | 0.9300 |
C17—H17 | 0.9300 | C47—C48 | 1.393 (4) |
C17—C18 | 1.380 (4) | C48—H48 | 0.9300 |
C18—H18 | 0.9300 | C49—C50 | 1.390 (4) |
C18—N5 | 1.344 (3) | C49—C54 | 1.403 (4) |
C19—C20 | 1.391 (4) | C49—P2 | 1.826 (3) |
C19—C24 | 1.396 (4) | C50—H50 | 0.9300 |
C19—P1 | 1.831 (3) | C50—C51 | 1.390 (4) |
C20—H20 | 0.9300 | C51—H51 | 0.9300 |
C20—C21 | 1.396 (4) | C51—C52 | 1.376 (4) |
C21—H21 | 0.9300 | C52—H52 | 0.9300 |
C21—C22 | 1.379 (4) | C52—C53 | 1.382 (5) |
C22—H22 | 0.9300 | C53—H53 | 0.9300 |
C22—C23 | 1.379 (5) | C53—C54 | 1.394 (4) |
C23—H23 | 0.9300 | C54—H54 | 0.9300 |
C23—C24 | 1.383 (4) | Cu1—N1 | 2.038 (3) |
C24—H24 | 0.9300 | Cu1—N5 | 2.150 (2) |
C25—C26 | 1.400 (4) | Cu1—P1 | 2.2306 (8) |
C25—C30 | 1.387 (4) | Cu1—P2 | 2.2479 (8) |
C25—P1 | 1.831 (3) | N2—H2A | 0.8600 |
C26—H26 | 0.9300 | F1—P3 | 1.6292 (18) |
C26—C27 | 1.390 (4) | F2—P3 | 1.6000 (18) |
C27—H27 | 0.9300 | F3—P3 | 1.613 (2) |
C27—C28 | 1.371 (5) | F4—P3 | 1.5990 (17) |
C28—H28 | 0.9300 | F5—P3 | 1.587 (2) |
C28—C29 | 1.388 (4) | F6—P3 | 1.587 (2) |
C29—H29 | 0.9300 | ||
N1—C1—C14 | 120.0 (3) | C35—C34—C33 | 120.3 (3) |
N1—C1—N2 | 116.4 (2) | C35—C34—H34 | 119.8 |
N2—C1—C14 | 123.5 (3) | C34—C35—H35 | 119.8 |
C3—C2—H2 | 108.5 | C34—C35—C36 | 120.3 (3) |
C4—C2—H2 | 108.5 | C36—C35—H35 | 119.8 |
C4—C2—C3 | 116.5 (2) | C31—C36—H36 | 120.0 |
N1—C2—H2 | 108.5 | C35—C36—C31 | 120.0 (3) |
N1—C2—C3 | 104.8 (2) | C35—C36—H36 | 120.0 |
N1—C2—C4 | 109.9 (2) | C38—C37—P2 | 116.3 (2) |
C2—C3—H3 | 109.7 | C42—C37—C38 | 118.3 (3) |
C9—C3—C2 | 112.7 (2) | C42—C37—P2 | 125.4 (2) |
C9—C3—H3 | 109.7 | C37—C38—H38 | 119.7 |
N2—C3—C2 | 102.0 (2) | C39—C38—C37 | 120.7 (3) |
N2—C3—H3 | 109.7 | C39—C38—H38 | 119.7 |
N2—C3—C9 | 112.8 (2) | C38—C39—H39 | 119.8 |
C5—C4—C2 | 120.7 (3) | C38—C39—C40 | 120.5 (3) |
N3—C4—C2 | 117.2 (2) | C40—C39—H39 | 119.8 |
N3—C4—C5 | 122.0 (3) | C39—C40—H40 | 120.2 |
C4—C5—H5 | 120.3 | C39—C40—C41 | 119.6 (3) |
C6—C5—C4 | 119.5 (3) | C41—C40—H40 | 120.2 |
C6—C5—H5 | 120.3 | C40—C41—H41 | 119.8 |
C5—C6—H6 | 120.7 | C42—C41—C40 | 120.3 (3) |
C7—C6—C5 | 118.6 (3) | C42—C41—H41 | 119.8 |
C7—C6—H6 | 120.7 | C37—C42—H42 | 119.7 |
C6—C7—H7 | 120.8 | C41—C42—C37 | 120.6 (3) |
C6—C7—C8 | 118.5 (3) | C41—C42—H42 | 119.7 |
C8—C7—H7 | 120.8 | C44—C43—P2 | 123.3 (2) |
C7—C8—H8 | 118.1 | C48—C43—C44 | 118.4 (3) |
N3—C8—C7 | 123.7 (3) | C48—C43—P2 | 118.2 (2) |
N3—C8—H8 | 118.1 | C43—C44—H44 | 119.7 |
C10—C9—C3 | 121.2 (3) | C45—C44—C43 | 120.5 (3) |
N4—C9—C3 | 116.3 (3) | C45—C44—H44 | 119.7 |
N4—C9—C10 | 122.4 (3) | C44—C45—H45 | 119.6 |
C9—C10—H10 | 120.5 | C46—C45—C44 | 120.7 (3) |
C11—C10—C9 | 119.0 (3) | C46—C45—H45 | 119.6 |
C11—C10—H10 | 120.5 | C45—C46—H46 | 120.3 |
C10—C11—H11 | 120.6 | C45—C46—C47 | 119.4 (3) |
C12—C11—C10 | 118.8 (3) | C47—C46—H46 | 120.3 |
C12—C11—H11 | 120.6 | C46—C47—H47 | 120.1 |
C11—C12—H12 | 120.6 | C46—C47—C48 | 119.9 (3) |
C11—C12—C13 | 118.8 (3) | C48—C47—H47 | 120.1 |
C13—C12—H12 | 120.6 | C43—C48—C47 | 121.0 (3) |
C12—C13—H13 | 118.2 | C43—C48—H48 | 119.5 |
N4—C13—C12 | 123.6 (3) | C47—C48—H48 | 119.5 |
N4—C13—H13 | 118.2 | C50—C49—C54 | 118.8 (3) |
C15—C14—C1 | 123.5 (3) | C50—C49—P2 | 122.2 (2) |
N5—C14—C1 | 113.6 (3) | C54—C49—P2 | 118.7 (2) |
N5—C14—C15 | 122.8 (3) | C49—C50—H50 | 119.9 |
C14—C15—H15 | 120.6 | C49—C50—C51 | 120.1 (3) |
C14—C15—C16 | 118.7 (3) | C51—C50—H50 | 119.9 |
C16—C15—H15 | 120.6 | C50—C51—H51 | 119.5 |
C15—C16—H16 | 120.6 | C52—C51—C50 | 121.0 (3) |
C17—C16—C15 | 118.8 (3) | C52—C51—H51 | 119.5 |
C17—C16—H16 | 120.6 | C51—C52—H52 | 120.2 |
C16—C17—H17 | 120.6 | C51—C52—C53 | 119.6 (3) |
C16—C17—C18 | 118.9 (3) | C53—C52—H52 | 120.2 |
C18—C17—H17 | 120.6 | C52—C53—H53 | 119.9 |
C17—C18—H18 | 118.4 | C52—C53—C54 | 120.3 (3) |
N5—C18—C17 | 123.2 (3) | C54—C53—H53 | 119.9 |
N5—C18—H18 | 118.4 | C49—C54—H54 | 119.9 |
C20—C19—C24 | 118.8 (3) | C53—C54—C49 | 120.3 (3) |
C20—C19—P1 | 118.6 (2) | C53—C54—H54 | 119.9 |
C24—C19—P1 | 122.6 (2) | N1—Cu1—N5 | 79.26 (9) |
C19—C20—H20 | 119.9 | N1—Cu1—P1 | 121.09 (7) |
C19—C20—C21 | 120.3 (3) | N1—Cu1—P2 | 104.87 (7) |
C21—C20—H20 | 119.9 | N5—Cu1—P1 | 108.16 (6) |
C20—C21—H21 | 120.0 | N5—Cu1—P2 | 113.97 (6) |
C22—C21—C20 | 120.1 (3) | P1—Cu1—P2 | 121.89 (3) |
C22—C21—H21 | 120.0 | C1—N1—C2 | 108.1 (3) |
C21—C22—H22 | 120.0 | C1—N1—Cu1 | 114.70 (19) |
C21—C22—C23 | 120.1 (3) | C2—N1—Cu1 | 137.18 (19) |
C23—C22—H22 | 120.0 | C1—N2—C3 | 108.6 (2) |
C22—C23—H23 | 119.9 | C1—N2—H2A | 125.7 |
C22—C23—C24 | 120.2 (3) | C3—N2—H2A | 125.7 |
C24—C23—H23 | 119.9 | C8—N3—C4 | 117.6 (3) |
C19—C24—H24 | 119.7 | C9—N4—C13 | 117.4 (3) |
C23—C24—C19 | 120.6 (3) | C14—N5—Cu1 | 112.38 (17) |
C23—C24—H24 | 119.7 | C18—N5—C14 | 117.6 (3) |
C26—C25—P1 | 120.1 (2) | C18—N5—Cu1 | 130.0 (2) |
C30—C25—C26 | 119.0 (3) | C19—P1—Cu1 | 115.57 (11) |
C30—C25—P1 | 120.3 (2) | C25—P1—C19 | 103.81 (13) |
C25—C26—H26 | 120.1 | C25—P1—Cu1 | 109.87 (9) |
C27—C26—C25 | 119.7 (3) | C31—P1—C19 | 103.10 (12) |
C27—C26—H26 | 120.1 | C31—P1—C25 | 106.44 (14) |
C26—C27—H27 | 119.4 | C31—P1—Cu1 | 116.88 (9) |
C28—C27—C26 | 121.1 (3) | C37—P2—C43 | 102.20 (13) |
C28—C27—H27 | 119.4 | C37—P2—C49 | 105.90 (13) |
C27—C28—H28 | 120.3 | C37—P2—Cu1 | 109.73 (9) |
C27—C28—C29 | 119.3 (3) | C43—P2—Cu1 | 117.87 (9) |
C29—C28—H28 | 120.3 | C49—P2—C43 | 104.74 (13) |
C28—C29—H29 | 119.8 | C49—P2—Cu1 | 115.06 (9) |
C28—C29—C30 | 120.3 (3) | F2—P3—F1 | 89.17 (10) |
C30—C29—H29 | 119.8 | F2—P3—F3 | 89.38 (12) |
C25—C30—C29 | 120.4 (3) | F3—P3—F1 | 88.70 (12) |
C25—C30—H30 | 119.8 | F4—P3—F1 | 89.02 (9) |
C29—C30—H30 | 119.8 | F4—P3—F2 | 177.93 (12) |
C32—C31—C36 | 119.4 (3) | F4—P3—F3 | 89.57 (12) |
C32—C31—P1 | 124.0 (2) | F5—P3—F1 | 88.99 (11) |
C36—C31—P1 | 116.3 (2) | F5—P3—F2 | 91.14 (12) |
C31—C32—H32 | 119.9 | F5—P3—F3 | 177.62 (12) |
C31—C32—C33 | 120.1 (3) | F5—P3—F4 | 89.84 (11) |
C33—C32—H32 | 119.9 | F6—P3—F1 | 178.97 (15) |
C32—C33—H33 | 120.1 | F6—P3—F2 | 91.03 (11) |
C34—C33—C32 | 119.9 (3) | F6—P3—F3 | 90.30 (14) |
C34—C33—H33 | 120.1 | F6—P3—F4 | 90.76 (11) |
C33—C34—H34 | 119.8 | F6—P3—F5 | 92.01 (14) |
C1—C14—C15—C16 | −178.6 (2) | C34—C35—C36—C31 | 0.0 (5) |
C1—C14—N5—C18 | 179.4 (2) | C36—C31—C32—C33 | 0.3 (4) |
C1—C14—N5—Cu1 | −0.3 (3) | C36—C31—P1—C19 | 95.7 (2) |
C2—C3—C9—C10 | −73.9 (4) | C36—C31—P1—C25 | −155.4 (2) |
C2—C3—C9—N4 | 103.9 (3) | C36—C31—P1—Cu1 | −32.3 (2) |
C2—C3—N2—C1 | −4.5 (3) | C37—C38—C39—C40 | 1.5 (4) |
C2—C4—C5—C6 | −175.4 (3) | C38—C37—C42—C41 | 0.8 (4) |
C2—C4—N3—C8 | 176.4 (3) | C38—C37—P2—C43 | −75.5 (2) |
C3—C2—C4—C5 | −59.7 (4) | C38—C37—P2—C49 | 175.1 (2) |
C3—C2—C4—N3 | 122.9 (3) | C38—C37—P2—Cu1 | 50.4 (2) |
C3—C2—N1—C1 | −1.3 (3) | C38—C39—C40—C41 | −0.4 (4) |
C3—C2—N1—Cu1 | −178.93 (19) | C39—C40—C41—C42 | −0.5 (4) |
C3—C9—C10—C11 | 177.2 (3) | C40—C41—C42—C37 | 0.3 (5) |
C3—C9—N4—C13 | −176.7 (3) | C42—C37—C38—C39 | −1.7 (4) |
C4—C2—C3—C9 | −113.7 (3) | C42—C37—P2—C43 | 105.4 (3) |
C4—C2—C3—N2 | 125.1 (2) | C42—C37—P2—C49 | −4.0 (3) |
C4—C2—N1—C1 | −127.2 (2) | C42—C37—P2—Cu1 | −128.8 (2) |
C4—C2—N1—Cu1 | 55.2 (3) | C43—C44—C45—C46 | −0.9 (5) |
C4—C5—C6—C7 | −1.1 (5) | C44—C43—C48—C47 | −0.9 (4) |
C5—C4—N3—C8 | −1.0 (5) | C44—C43—P2—C37 | −42.4 (3) |
C5—C6—C7—C8 | −0.5 (5) | C44—C43—P2—C49 | 67.9 (3) |
C6—C7—C8—N3 | 1.5 (5) | C44—C43—P2—Cu1 | −162.7 (2) |
C7—C8—N3—C4 | −0.7 (5) | C44—C45—C46—C47 | 0.9 (5) |
C9—C3—N2—C1 | −125.7 (3) | C45—C46—C47—C48 | −0.9 (5) |
C9—C10—C11—C12 | −0.7 (6) | C46—C47—C48—C43 | 0.9 (5) |
C10—C9—N4—C13 | 1.0 (5) | C48—C43—C44—C45 | 0.9 (5) |
C10—C11—C12—C13 | 1.0 (6) | C48—C43—P2—C37 | 135.2 (2) |
C11—C12—C13—N4 | −0.4 (6) | C48—C43—P2—C49 | −114.5 (2) |
C12—C13—N4—C9 | −0.6 (5) | C48—C43—P2—Cu1 | 14.9 (3) |
C14—C1—N1—C2 | −179.2 (2) | C49—C50—C51—C52 | −0.6 (5) |
C14—C1—N1—Cu1 | −1.0 (3) | C50—C49—C54—C53 | −0.8 (4) |
C14—C1—N2—C3 | −178.4 (2) | C50—C49—P2—C37 | 123.5 (2) |
C14—C15—C16—C17 | −0.8 (4) | C50—C49—P2—C43 | 15.9 (3) |
C15—C14—N5—C18 | 0.8 (4) | C50—C49—P2—Cu1 | −115.1 (2) |
C15—C14—N5—Cu1 | −178.9 (2) | C50—C51—C52—C53 | 0.2 (5) |
C15—C16—C17—C18 | 0.9 (4) | C51—C52—C53—C54 | −0.1 (5) |
C16—C17—C18—N5 | −0.2 (4) | C52—C53—C54—C49 | 0.4 (4) |
C17—C18—N5—C14 | −0.7 (4) | C54—C49—C50—C51 | 0.9 (4) |
C17—C18—N5—Cu1 | 179.00 (19) | C54—C49—P2—C37 | −62.8 (2) |
C19—C20—C21—C22 | −0.1 (5) | C54—C49—P2—C43 | −170.4 (2) |
C20—C19—C24—C23 | 0.4 (4) | C54—C49—P2—Cu1 | 58.6 (2) |
C20—C19—P1—C25 | 94.5 (3) | N1—C1—C14—C15 | 179.4 (3) |
C20—C19—P1—C31 | −154.7 (2) | N1—C1—C14—N5 | 0.8 (4) |
C20—C19—P1—Cu1 | −25.9 (3) | N1—C1—N2—C3 | 4.3 (3) |
C20—C21—C22—C23 | 0.4 (5) | N1—C2—C3—C9 | 124.6 (2) |
C21—C22—C23—C24 | −0.3 (5) | N1—C2—C3—N2 | 3.5 (3) |
C22—C23—C24—C19 | −0.1 (5) | N1—C2—C4—C5 | 59.2 (4) |
C24—C19—C20—C21 | −0.3 (5) | N1—C2—C4—N3 | −118.2 (3) |
C24—C19—P1—C25 | −87.3 (3) | N2—C1—C14—C15 | 2.2 (4) |
C24—C19—P1—C31 | 23.5 (3) | N2—C1—C14—N5 | −176.4 (2) |
C24—C19—P1—Cu1 | 152.3 (2) | N2—C1—N1—C2 | −1.8 (3) |
C25—C26—C27—C28 | −1.1 (5) | N2—C1—N1—Cu1 | 176.45 (18) |
C26—C25—C30—C29 | 0.1 (4) | N2—C3—C9—C10 | 40.9 (4) |
C26—C25—P1—C19 | −37.0 (3) | N2—C3—C9—N4 | −141.3 (3) |
C26—C25—P1—C31 | −145.5 (2) | N3—C4—C5—C6 | 1.9 (5) |
C26—C25—P1—Cu1 | 87.1 (2) | N4—C9—C10—C11 | −0.4 (5) |
C26—C27—C28—C29 | −0.7 (5) | N5—C14—C15—C16 | −0.1 (4) |
C27—C28—C29—C30 | 2.1 (5) | P1—C19—C20—C21 | 178.0 (2) |
C28—C29—C30—C25 | −1.8 (5) | P1—C19—C24—C23 | −177.8 (2) |
C30—C25—C26—C27 | 1.4 (4) | P1—C25—C26—C27 | −169.7 (2) |
C30—C25—P1—C19 | 152.0 (2) | P1—C25—C30—C29 | 171.1 (2) |
C30—C25—P1—C31 | 43.6 (3) | P1—C31—C32—C33 | 174.1 (2) |
C30—C25—P1—Cu1 | −83.8 (2) | P1—C31—C36—C35 | −174.2 (2) |
C31—C32—C33—C34 | −0.6 (5) | P2—C37—C38—C39 | 179.1 (2) |
C32—C31—C36—C35 | 0.0 (4) | P2—C37—C42—C41 | 180.0 (2) |
C32—C31—P1—C19 | −78.3 (3) | P2—C43—C44—C45 | 178.5 (2) |
C32—C31—P1—C25 | 30.7 (3) | P2—C43—C48—C47 | −178.7 (2) |
C32—C31—P1—Cu1 | 153.8 (2) | P2—C49—C50—C51 | 174.6 (2) |
C32—C33—C34—C35 | 0.6 (5) | P2—C49—C54—C53 | −174.7 (2) |
C33—C34—C35—C36 | −0.2 (5) |
Cg1 is the centroid of the C9–C13/N4 ring and Cg2 is the centroid of the C43–C48 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···F5i | 0.93 | 2.48 | 3.339 (4) | 153 |
C15—H15···F1 | 0.93 | 2.49 | 3.259 (4) | 141 |
C17—H17···F4ii | 0.93 | 2.59 | 3.260 (4) | 130 |
C17—H17···F3ii | 0.93 | 2.66 | 3.586 (4) | 174 |
C27—H27···F1ii | 0.93 | 2.65 | 3.404 (4) | 139 |
C33—H33···F1iii | 0.93 | 2.58 | 3.336 (4) | 138 |
C34—H34···Cg1iii | 0.93 | 2.82 | 3.517 | 133 |
C39—H39···Cg2iv | 0.93 | 2.59 | 3.467 (4) | 158 |
C40—H40···F4v | 0.93 | 2.59 | 3.249 (3) | 129 |
N2—H2A···F1 | 0.86 | 2.32 | 2.975 (3) | 133 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register