The four title CuII compounds are chloro[(2-furylmethyl)bis(2-pyridylmethyl)amine-N,N',N'']copper(II) perchlorate, [CuCl(C17H17N3O)]ClO4, (I), chloro{2-[bis(2-pyridylmethyl)amino]ethanolato-N,N',N'',O}copper(II) hemi[tetrachlorocopper(II)], [CuCl(C14H17N3O)][CuCl4]1/2, (II), chloro[(2-morpholinoethyl)bis(2-pyridylmethyl)amine-N,N',N'',N''']copper(II) perchlorate, [CuCl(C18H24N4O)]ClO4, (III), and chloro[(2-piperidinylethyl)bis(2-pyridylmethyl)amine-N,N',N'',N''']copper(II) hexafluorophosphate, [CuCl(C19H26N4)]PF6, (IV). They have tripodal potentially tetradentate ligands. In (I), the O atom of the furan moiety weakly coordinates to the Cu atom at a distance of 2.750 (3) Å.
Supporting information
CCDC references: 146078; 146079; 146080; 146081
For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (III), (IV); DIRDIF94 (Beurskens et al., 1994) for (II). For all compounds, program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
[CuCl(C17H17N3O)]ClO4 | Z = 4 |
Mr = 477.79 | Dx = 1.637 Mg m−3 |
Triclinic, P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.658 (2) Å | Cell parameters from 25 reflections |
b = 14.199 (3) Å | θ = 10–15° |
c = 11.720 (3) Å | µ = 1.44 mm−1 |
α = 104.92 (2)° | T = 299 K |
β = 112.08 (2)° | Plate, blue- |
γ = 68.32 (1)° | 0.5 × 0.4 × 0.2 mm |
V = 1938.5 (8) Å3 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.011 |
θ–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→18 |
Tmin = 0.477, Tmax = 0.780 | k = −18→18 |
9268 measured reflections | l = −15→15 |
8895 independent reflections | 3 standard reflections every 100 reflections |
6332 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.148 | (Δ/σ)max = 0.003 |
S = 0.99 | Δρmax = 0.42 e Å−3 |
8895 reflections | Δρmin = −0.53 e Å−3 |
505 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.49866 (3) | 0.49143 (3) | 0.34506 (4) | 0.0383 (1) | |
Cu2 | 0.94462 (3) | 0.90680 (3) | 0.39059 (4) | 0.0417 (1) | |
Cl1 | 0.38467 (8) | 0.61852 (6) | 0.43799 (8) | 0.0498 (2) | |
Cl2 | 1.08464 (8) | 0.87583 (7) | 0.56800 (9) | 0.0526 (2) | |
Cl3 | 0.57409 (8) | 0.09827 (8) | −0.11273 (9) | 0.0549 (3) | |
Cl4 | 1.01086 (9) | 0.7156 (1) | 0.7826 (1) | 0.0698 (3) | |
O1 | 0.3908 (2) | 0.5272 (2) | 0.1024 (2) | 0.0516 (7) | |
O2 | 0.9373 (3) | 0.7027 (3) | 0.2866 (3) | 0.075 (1) | |
O3 | 0.6413 (4) | 0.1478 (4) | −0.0197 (5) | 0.147 (2) | |
O4 | 0.6341 (5) | 0.0016 (3) | −0.1512 (5) | 0.136 (2) | |
O5 | 0.5202 (9) | 0.1483 (6) | −0.2097 (6) | 0.265 (4) | |
O6 | 0.4984 (7) | 0.1006 (7) | −0.0636 (9) | 0.242 (5) | |
O7 | 0.9923 (4) | 0.6825 (4) | 0.6551 (4) | 0.127 (2) | |
O8 | 1.0314 (4) | 0.6382 (5) | 0.8488 (7) | 0.161 (3) | |
O9 | 0.9158 (3) | 0.7944 (3) | 0.8006 (4) | 0.101 (1) | |
O10 | 1.1042 (4) | 0.7489 (5) | 0.8269 (4) | 0.133 (2) | |
N1 | 0.4116 (2) | 0.3942 (2) | 0.2886 (3) | 0.0415 (7) | |
N2 | 0.5984 (2) | 0.3806 (2) | 0.2532 (2) | 0.0397 (7) | |
N3 | 0.6106 (3) | 0.5609 (2) | 0.3778 (3) | 0.0493 (8) | |
N4 | 1.0369 (2) | 0.8773 (2) | 0.2825 (3) | 0.0466 (8) | |
N5 | 0.8169 (2) | 0.9257 (2) | 0.2274 (3) | 0.0491 (8) | |
N6 | 0.8206 (2) | 0.9411 (2) | 0.4584 (3) | 0.0480 (8) | |
C1 | 0.3086 (3) | 0.4132 (3) | 0.2912 (4) | 0.053 (1) | |
C2 | 0.2555 (4) | 0.3399 (4) | 0.2508 (4) | 0.064 (1) | |
C3 | 0.3102 (4) | 0.2428 (3) | 0.2047 (4) | 0.062 (1) | |
C4 | 0.4156 (3) | 0.2223 (3) | 0.1994 (4) | 0.053 (1) | |
C5 | 0.4649 (3) | 0.2995 (2) | 0.2438 (3) | 0.0418 (8) | |
C6 | 0.5822 (3) | 0.2827 (2) | 0.2503 (3) | 0.0443 (9) | |
C7 | 0.7133 (3) | 0.3855 (3) | 0.3258 (4) | 0.052 (1) | |
C8 | 0.7080 (3) | 0.4960 (3) | 0.3653 (3) | 0.050 (1) | |
C9 | 0.7975 (4) | 0.5313 (4) | 0.3883 (4) | 0.068 (1) | |
C10 | 0.7836 (5) | 0.6348 (5) | 0.4236 (5) | 0.082 (2) | |
C11 | 0.6843 (5) | 0.6999 (4) | 0.4323 (5) | 0.080 (2) | |
C12 | 0.5973 (4) | 0.6620 (3) | 0.4090 (4) | 0.066 (1) | |
C13 | 0.5699 (3) | 0.4025 (3) | 0.1233 (3) | 0.0472 (10) | |
C14 | 0.4498 (3) | 0.4322 (3) | 0.0590 (3) | 0.0444 (9) | |
C15 | 0.3798 (4) | 0.3878 (3) | −0.0363 (4) | 0.058 (1) | |
C16 | 0.2726 (4) | 0.4577 (4) | −0.0529 (4) | 0.065 (1) | |
C17 | 0.2822 (4) | 0.5396 (3) | 0.0305 (4) | 0.061 (1) | |
C18 | 1.1471 (3) | 0.8291 (3) | 0.3085 (4) | 0.053 (1) | |
C19 | 1.2019 (4) | 0.8143 (4) | 0.2257 (4) | 0.064 (1) | |
C20 | 1.1429 (4) | 0.8471 (4) | 0.1114 (5) | 0.068 (1) | |
C21 | 1.0305 (4) | 0.8930 (3) | 0.0825 (4) | 0.064 (1) | |
C22 | 0.9793 (3) | 0.9075 (3) | 0.1697 (4) | 0.051 (1) | |
C23 | 0.8571 (4) | 0.9599 (3) | 0.1474 (4) | 0.060 (1) | |
C24 | 0.7206 (3) | 1.0049 (3) | 0.2603 (4) | 0.057 (1) | |
C25 | 0.7216 (3) | 0.9900 (3) | 0.3826 (4) | 0.0520 (10) | |
C26 | 0.6283 (3) | 1.0283 (4) | 0.4216 (5) | 0.067 (1) | |
C27 | 0.6383 (4) | 1.0168 (4) | 0.5397 (5) | 0.073 (1) | |
C28 | 0.7390 (4) | 0.9634 (4) | 0.6135 (4) | 0.062 (1) | |
C29 | 0.8287 (3) | 0.9266 (3) | 0.5712 (4) | 0.055 (1) | |
C30 | 0.7872 (3) | 0.8284 (3) | 0.1690 (4) | 0.060 (1) | |
C31 | 0.8843 (3) | 0.7365 (3) | 0.1736 (4) | 0.054 (1) | |
C32 | 0.9380 (4) | 0.6765 (4) | 0.0918 (5) | 0.071 (1) | |
C33 | 1.0282 (5) | 0.6001 (4) | 0.1583 (7) | 0.088 (2) | |
C34 | 1.0244 (5) | 0.6187 (4) | 0.2730 (7) | 0.093 (2) | |
H1 | 0.2705 | 0.4809 | 0.3226 | 0.0632* | |
H2 | 0.1820 | 0.3557 | 0.2545 | 0.0766* | |
H3 | 0.2752 | 0.1899 | 0.1766 | 0.0742* | |
H4 | 0.4539 | 0.1557 | 0.1655 | 0.0632* | |
H5 | 0.5971 | 0.2366 | 0.1786 | 0.0531* | |
H6 | 0.6323 | 0.2534 | 0.3242 | 0.0531* | |
H7 | 0.7413 | 0.3514 | 0.3978 | 0.0620* | |
H8 | 0.7610 | 0.3531 | 0.2749 | 0.0620* | |
H9 | 0.8670 | 0.4847 | 0.3798 | 0.0817* | |
H10 | 0.8444 | 0.6607 | 0.4421 | 0.0990* | |
H11 | 0.6740 | 0.7721 | 0.4545 | 0.0961* | |
H12 | 0.5269 | 0.7083 | 0.4152 | 0.0793* | |
H13 | 0.5971 | 0.4573 | 0.1280 | 0.0566* | |
H14 | 0.6052 | 0.3422 | 0.0764 | 0.0566* | |
H15 | 0.3995 | 0.3214 | −0.0834 | 0.0691* | |
H16 | 0.2052 | 0.4480 | −0.1133 | 0.0778* | |
H17 | 0.2214 | 0.5994 | 0.0395 | 0.0737* | |
H18 | 1.1880 | 0.8045 | 0.3873 | 0.0641* | |
H19 | 1.2805 | 0.7814 | 0.2470 | 0.0772* | |
H20 | 1.1802 | 0.8379 | 0.0524 | 0.0822* | |
H21 | 0.9879 | 0.9148 | 0.0024 | 0.0766* | |
H22 | 0.8177 | 0.9432 | 0.0616 | 0.0718* | |
H23 | 0.8438 | 1.0326 | 0.1669 | 0.0718* | |
H24 | 0.7258 | 1.0717 | 0.2665 | 0.0689* | |
H25 | 0.6530 | 0.9983 | 0.1974 | 0.0689* | |
H26 | 0.5576 | 1.0623 | 0.3674 | 0.0805* | |
H27 | 0.5754 | 1.0459 | 0.5697 | 0.0876* | |
H28 | 0.7463 | 0.9519 | 0.6939 | 0.0748* | |
H29 | 0.8990 | 0.8897 | 0.6231 | 0.0660* | |
H30 | 0.7439 | 0.8203 | 0.2119 | 0.0723* | |
H31 | 0.7438 | 0.8341 | 0.0835 | 0.0723* | |
H32 | 0.9192 | 0.6839 | 0.0063 | 0.0847* | |
H33 | 1.0818 | 0.5454 | 0.1258 | 0.1056* | |
H34 | 1.0758 | 0.5786 | 0.3380 | 0.1112* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0366 (2) | 0.0348 (2) | 0.0426 (2) | −0.0069 (2) | 0.0165 (2) | 0.0020 (2) |
Cu2 | 0.0342 (2) | 0.0457 (2) | 0.0406 (2) | −0.0064 (2) | 0.0080 (2) | 0.0113 (2) |
Cl1 | 0.0480 (5) | 0.0418 (4) | 0.0490 (5) | 0.0020 (4) | 0.0197 (4) | 0.0033 (3) |
Cl2 | 0.0438 (5) | 0.0605 (5) | 0.0484 (5) | −0.0093 (4) | 0.0053 (4) | 0.0209 (4) |
Cl3 | 0.0479 (5) | 0.0580 (5) | 0.0538 (5) | −0.0130 (4) | 0.0194 (4) | −0.0036 (4) |
Cl4 | 0.0457 (5) | 0.0917 (8) | 0.0722 (7) | −0.0143 (5) | 0.0145 (5) | 0.0244 (6) |
O1 | 0.052 (1) | 0.048 (1) | 0.052 (1) | −0.007 (1) | 0.019 (1) | 0.008 (1) |
O2 | 0.071 (2) | 0.078 (2) | 0.082 (2) | −0.008 (2) | 0.031 (2) | 0.030 (2) |
O3 | 0.110 (4) | 0.136 (4) | 0.162 (5) | −0.053 (3) | 0.042 (3) | −0.063 (4) |
O4 | 0.168 (5) | 0.063 (2) | 0.152 (4) | 0.002 (3) | 0.077 (4) | −0.017 (3) |
O5 | 0.37 (1) | 0.164 (6) | 0.109 (4) | 0.080 (7) | 0.038 (6) | 0.055 (4) |
O6 | 0.230 (9) | 0.28 (1) | 0.33 (1) | −0.144 (8) | 0.210 (9) | −0.061 (9) |
O7 | 0.109 (3) | 0.136 (4) | 0.083 (3) | −0.024 (3) | 0.003 (2) | −0.013 (3) |
O8 | 0.106 (4) | 0.161 (5) | 0.236 (7) | 0.017 (3) | 0.052 (4) | 0.140 (5) |
O9 | 0.064 (2) | 0.101 (3) | 0.127 (3) | −0.005 (2) | 0.029 (2) | 0.021 (3) |
O10 | 0.097 (3) | 0.235 (6) | 0.100 (3) | −0.103 (4) | 0.052 (3) | −0.039 (3) |
N1 | 0.039 (1) | 0.043 (1) | 0.039 (1) | −0.008 (1) | 0.013 (1) | 0.006 (1) |
N2 | 0.039 (1) | 0.041 (1) | 0.040 (1) | −0.005 (1) | 0.017 (1) | 0.009 (1) |
N3 | 0.049 (2) | 0.051 (2) | 0.052 (2) | −0.018 (1) | 0.014 (1) | 0.010 (1) |
N4 | 0.043 (2) | 0.047 (2) | 0.047 (2) | −0.011 (1) | 0.012 (1) | 0.007 (1) |
N5 | 0.041 (2) | 0.049 (2) | 0.047 (2) | −0.005 (1) | 0.008 (1) | 0.009 (1) |
N6 | 0.043 (2) | 0.048 (2) | 0.052 (2) | −0.010 (1) | 0.015 (1) | 0.011 (1) |
C1 | 0.045 (2) | 0.056 (2) | 0.058 (2) | −0.014 (2) | 0.020 (2) | 0.004 (2) |
C2 | 0.051 (2) | 0.079 (3) | 0.068 (3) | −0.027 (2) | 0.017 (2) | 0.010 (2) |
C3 | 0.070 (3) | 0.062 (2) | 0.060 (2) | −0.035 (2) | 0.012 (2) | 0.007 (2) |
C4 | 0.063 (2) | 0.047 (2) | 0.052 (2) | −0.020 (2) | 0.017 (2) | 0.007 (2) |
C5 | 0.050 (2) | 0.039 (2) | 0.036 (2) | −0.010 (1) | 0.013 (1) | 0.008 (1) |
C6 | 0.050 (2) | 0.036 (2) | 0.046 (2) | −0.003 (1) | 0.022 (2) | 0.008 (1) |
C7 | 0.035 (2) | 0.062 (2) | 0.056 (2) | −0.006 (2) | 0.015 (2) | 0.015 (2) |
C8 | 0.042 (2) | 0.069 (2) | 0.044 (2) | −0.019 (2) | 0.010 (2) | 0.013 (2) |
C9 | 0.056 (2) | 0.098 (3) | 0.060 (2) | −0.038 (2) | 0.013 (2) | 0.011 (2) |
C10 | 0.089 (4) | 0.109 (4) | 0.072 (3) | −0.064 (3) | 0.017 (3) | 0.006 (3) |
C11 | 0.101 (4) | 0.075 (3) | 0.087 (3) | −0.057 (3) | 0.030 (3) | −0.003 (3) |
C12 | 0.071 (3) | 0.056 (2) | 0.074 (3) | −0.027 (2) | 0.020 (2) | 0.005 (2) |
C13 | 0.051 (2) | 0.052 (2) | 0.046 (2) | −0.011 (2) | 0.023 (2) | 0.011 (2) |
C14 | 0.053 (2) | 0.044 (2) | 0.040 (2) | −0.010 (1) | 0.018 (2) | 0.012 (1) |
C15 | 0.069 (3) | 0.055 (2) | 0.050 (2) | −0.024 (2) | 0.013 (2) | 0.007 (2) |
C16 | 0.056 (2) | 0.076 (3) | 0.063 (3) | −0.023 (2) | 0.003 (2) | 0.027 (2) |
C17 | 0.051 (2) | 0.066 (2) | 0.070 (3) | −0.008 (2) | 0.019 (2) | 0.025 (2) |
C18 | 0.047 (2) | 0.054 (2) | 0.056 (2) | −0.013 (2) | 0.014 (2) | 0.007 (2) |
C19 | 0.052 (2) | 0.073 (3) | 0.071 (3) | −0.019 (2) | 0.028 (2) | −0.002 (2) |
C20 | 0.077 (3) | 0.075 (3) | 0.073 (3) | −0.029 (2) | 0.041 (3) | 0.002 (2) |
C21 | 0.083 (3) | 0.065 (2) | 0.052 (2) | −0.026 (2) | 0.025 (2) | 0.010 (2) |
C22 | 0.060 (2) | 0.044 (2) | 0.049 (2) | −0.014 (2) | 0.017 (2) | 0.007 (2) |
C23 | 0.056 (2) | 0.065 (2) | 0.047 (2) | −0.005 (2) | 0.009 (2) | 0.019 (2) |
C24 | 0.039 (2) | 0.057 (2) | 0.059 (2) | 0.000 (2) | 0.007 (2) | 0.010 (2) |
C25 | 0.042 (2) | 0.048 (2) | 0.059 (2) | −0.007 (2) | 0.014 (2) | 0.004 (2) |
C26 | 0.045 (2) | 0.069 (3) | 0.077 (3) | −0.007 (2) | 0.019 (2) | 0.005 (2) |
C27 | 0.056 (3) | 0.078 (3) | 0.093 (3) | −0.022 (2) | 0.038 (3) | −0.006 (3) |
C28 | 0.064 (3) | 0.073 (3) | 0.065 (3) | −0.027 (2) | 0.029 (2) | 0.007 (2) |
C29 | 0.052 (2) | 0.059 (2) | 0.059 (2) | −0.016 (2) | 0.018 (2) | 0.014 (2) |
C30 | 0.046 (2) | 0.062 (2) | 0.062 (2) | −0.016 (2) | 0.008 (2) | 0.001 (2) |
C31 | 0.049 (2) | 0.052 (2) | 0.060 (2) | −0.021 (2) | 0.010 (2) | 0.006 (2) |
C32 | 0.071 (3) | 0.063 (3) | 0.072 (3) | −0.022 (2) | 0.023 (2) | −0.008 (2) |
C33 | 0.070 (3) | 0.064 (3) | 0.124 (5) | −0.010 (2) | 0.036 (3) | 0.004 (3) |
C34 | 0.078 (4) | 0.075 (3) | 0.125 (5) | 0.004 (3) | 0.033 (4) | 0.047 (3) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.248 (1) | C7—H7 | 0.960 |
Cu1—Cl1i | 2.933 (1) | C7—H8 | 0.960 |
Cu1—O1 | 2.750 (3) | C8—C9 | 1.397 (6) |
Cu1—N1 | 1.977 (3) | C9—C10 | 1.381 (7) |
Cu1—N2 | 2.034 (3) | C9—H9 | 0.960 |
Cu1—N3 | 1.984 (3) | C10—C11 | 1.354 (8) |
Cu2—Cl2 | 2.244 (1) | C10—H10 | 0.960 |
Cu2—Cl2ii | 2.896 (1) | C11—C12 | 1.389 (7) |
Cu2—O2 | 2.864 (4) | C11—H11 | 0.960 |
Cu2—N4 | 1.977 (3) | C12—H12 | 0.960 |
Cu2—N5 | 2.046 (3) | C13—C14 | 1.469 (5) |
Cu2—N6 | 1.985 (3) | C13—H13 | 0.960 |
Cl3—O3 | 1.362 (5) | C13—H14 | 0.960 |
Cl3—O4 | 1.373 (4) | C14—C15 | 1.357 (5) |
Cl3—O5 | 1.318 (6) | C15—C16 | 1.406 (6) |
Cl3—O6 | 1.347 (6) | C15—H15 | 0.960 |
Cl4—O7 | 1.400 (4) | C16—C17 | 1.324 (6) |
Cl4—O8 | 1.392 (5) | C16—H16 | 0.960 |
Cl4—O9 | 1.412 (4) | C17—H17 | 0.960 |
Cl4—O10 | 1.393 (4) | C18—C19 | 1.368 (6) |
O1—C14 | 1.371 (4) | C18—H18 | 0.960 |
O1—C17 | 1.373 (5) | C19—C20 | 1.376 (7) |
O2—C31 | 1.363 (5) | C19—H19 | 0.960 |
O2—C34 | 1.363 (6) | C20—C21 | 1.372 (7) |
N1—C1 | 1.342 (5) | C20—H20 | 0.960 |
N1—C5 | 1.347 (4) | C21—C22 | 1.378 (6) |
N2—C6 | 1.477 (4) | C21—H21 | 0.960 |
N2—C7 | 1.496 (5) | C22—C23 | 1.504 (6) |
N2—C13 | 1.508 (4) | C23—H22 | 0.960 |
N3—C8 | 1.346 (5) | C23—H23 | 0.960 |
N3—C12 | 1.346 (5) | C24—C25 | 1.496 (6) |
N4—C18 | 1.352 (5) | C24—H24 | 0.960 |
N4—C22 | 1.345 (5) | C24—H25 | 0.960 |
N5—C23 | 1.495 (5) | C25—C26 | 1.388 (6) |
N5—C24 | 1.486 (5) | C26—C27 | 1.385 (7) |
N5—C30 | 1.504 (5) | C26—H26 | 0.960 |
N6—C25 | 1.349 (5) | C27—C28 | 1.374 (7) |
N6—C29 | 1.348 (5) | C27—H27 | 0.960 |
C1—C2 | 1.370 (6) | C28—C29 | 1.367 (6) |
C1—H1 | 0.960 | C28—H28 | 0.960 |
C2—C3 | 1.383 (6) | C29—H29 | 0.960 |
C2—H2 | 0.960 | C30—C31 | 1.472 (6) |
C3—C4 | 1.382 (6) | C30—H30 | 0.960 |
C3—H3 | 0.960 | C30—H31 | 0.960 |
C4—C5 | 1.383 (5) | C31—C32 | 1.353 (6) |
C4—H4 | 0.960 | C32—C33 | 1.424 (8) |
C5—C6 | 1.505 (5) | C32—H32 | 0.960 |
C6—H5 | 0.960 | C33—C34 | 1.319 (9) |
C6—H6 | 0.960 | C33—H33 | 0.960 |
C7—C8 | 1.500 (6) | C34—H34 | 0.960 |
| | | |
Cu1···Cl1i | 2.933 (1) | O6···O6vi | 3.53 (2) |
Cu1···Cu1i | 3.5640 (8) | O6···C24iii | 3.585 (9) |
Cu2···Cl2ii | 2.896 (1) | O7···C10 | 3.258 (7) |
Cu2···Cu2ii | 3.5237 (8) | O7···C9viii | 3.403 (7) |
Cl1···N1i | 3.356 (3) | O7···C29 | 3.516 (7) |
Cl1···C6i | 3.480 (4) | O8···C17ix | 3.276 (7) |
Cl1···C7i | 3.518 (4) | O8···C16ix | 3.344 (7) |
Cl1···N2i | 3.536 (3) | O8···C32x | 3.384 (8) |
Cl2···C24ii | 3.398 (4) | O8···C2i | 3.559 (7) |
Cl2···N6ii | 3.424 (3) | O9···C21x | 3.267 (6) |
Cl2···N5ii | 3.520 (3) | O9···C29 | 3.273 (6) |
Cl2···C23ii | 3.545 (4) | O9···C28 | 3.293 (6) |
Cl2···N4ii | 3.583 (3) | O9···C3i | 3.296 (6) |
O1···C13iii | 3.332 (4) | O9···C2i | 3.336 (6) |
O2···C10 | 3.570 (6) | O10···C20x | 3.188 (6) |
O3···C6 | 3.463 (6) | O10···C7viii | 3.338 (6) |
O3···C23iv | 3.490 (8) | O10···C21x | 3.430 (6) |
O3···C13 | 3.513 (6) | N3···C1i | 3.571 (5) |
O3···C20v | 3.525 (8) | C1···C12i | 3.558 (6) |
O4···C3vi | 3.210 (6) | C13···C14iii | 3.439 (5) |
O4···C4vi | 3.357 (6) | C13···C17iii | 3.569 (6) |
O4···C28vii | 3.402 (7) | C14···C14iii | 3.500 (7) |
O5···C11iii | 3.496 (9) | C18···C29ii | 3.480 (6) |
O5···C12iii | 3.538 (8) | C18···C28ii | 3.588 (6) |
O6···C30iii | 3.446 (10) | C19···C28ii | 3.443 (6) |
O6···C4 | 3.492 (9) | | |
| | | |
Cl1—Cu1—O1 | 99.7 (1) | N3—C8—C7 | 115.8 (3) |
Cl1—Cu1—N1 | 97.3 (1) | N3—C8—C9 | 121.0 (4) |
Cl1—Cu1—N2 | 177.0 (1) | C7—C8—C9 | 123.1 (4) |
Cl1—Cu1—N3 | 97.6 (1) | C8—C9—C10 | 118.4 (5) |
O1—Cu1—Cl1i | 160.22 (6) | C8—C9—H9 | 120.8 |
O1—Cu1—N1 | 80.5 (1) | C10—C9—H9 | 120.8 |
O1—Cu1—N2 | 77.4 (1) | C9—C10—C11 | 120.1 (4) |
O1—Cu1—N3 | 96.0 (1) | C9—C10—H10 | 119.9 |
N1—Cu1—N2 | 83.3 (1) | C11—C10—H10 | 119.9 |
N1—Cu1—N3 | 165.1 (1) | C10—C11—C12 | 119.8 (5) |
N2—Cu1—N3 | 81.8 (1) | C10—C11—H11 | 120.1 |
Cl2—Cu2—O2 | 100.0 (1) | C12—C11—H11 | 120.1 |
Cl2—Cu2—N4 | 96.9 (1) | N3—C12—C11 | 120.7 (5) |
Cl2—Cu2—N5 | 176.4 (1) | N3—C12—H12 | 119.7 |
Cl2—Cu2—N6 | 97.8 (1) | C11—C12—H12 | 119.7 |
O2—Cu2—Cl2ii | 165.23 (7) | N2—C13—C14 | 112.4 (3) |
O2—Cu2—N4 | 82.4 (1) | N2—C13—H13 | 108.7 |
O2—Cu2—N5 | 76.5 (1) | N2—C13—H14 | 108.7 |
O2—Cu2—N6 | 94.2 (1) | C14—C13—H13 | 108.7 |
N4—Cu2—N5 | 83.4 (1) | C14—C13—H14 | 108.7 |
N4—Cu2—N6 | 165.3 (1) | H13—C13—H14 | 109.5 |
N5—Cu2—N6 | 81.9 (1) | O1—C14—C13 | 115.2 (3) |
Cu1—Cl1i—Cu1i | 85.85 (3) | O1—C14—C15 | 109.5 (3) |
Cu2—Cl2ii—Cu2ii | 85.58 (3) | C13—C14—C15 | 135.3 (3) |
O3—Cl3—O4 | 111.0 (4) | C14—C15—C16 | 106.8 (4) |
O3—Cl3—O5 | 111.7 (5) | C14—C15—H15 | 126.6 |
O3—Cl3—O6 | 104.0 (5) | C16—C15—H15 | 126.6 |
O4—Cl3—O5 | 108.4 (4) | C15—C16—C17 | 107.1 (4) |
O4—Cl3—O6 | 114.4 (5) | C15—C16—H16 | 126.4 |
O5—Cl3—O6 | 107.3 (7) | C17—C16—H16 | 126.4 |
O7—Cl4—O8 | 112.9 (4) | O1—C17—C16 | 110.8 (4) |
O7—Cl4—O9 | 109.1 (3) | O1—C17—H17 | 124.6 |
O7—Cl4—O10 | 107.2 (3) | C16—C17—H17 | 124.6 |
O8—Cl4—O9 | 107.6 (3) | N4—C18—C19 | 121.9 (4) |
O8—Cl4—O10 | 108.1 (4) | N4—C18—H18 | 119.1 |
O9—Cl4—O10 | 112.1 (3) | C19—C18—H18 | 119.1 |
Cu1—O1—C14 | 91.8 (2) | C18—C19—C20 | 119.2 (4) |
Cu1—O1—C17 | 131.1 (2) | C18—C19—H19 | 120.4 |
C14—O1—C17 | 105.8 (3) | C20—C19—H19 | 120.4 |
Cu2—O2—C31 | 87.5 (2) | C19—C20—C21 | 119.3 (4) |
Cu2—O2—C34 | 127.0 (4) | C19—C20—H20 | 120.3 |
C31—O2—C34 | 106.7 (4) | C21—C20—H20 | 120.3 |
Cu1—N1—C1 | 127.1 (2) | C20—C21—C22 | 119.3 (4) |
Cu1—N1—C5 | 114.1 (2) | C20—C21—H21 | 120.4 |
C1—N1—C5 | 118.8 (3) | C22—C21—H21 | 120.4 |
Cu1—N2—C6 | 107.0 (2) | N4—C22—C21 | 121.6 (4) |
Cu1—N2—C7 | 105.2 (2) | N4—C22—C23 | 115.5 (3) |
Cu1—N2—C13 | 110.9 (2) | C21—C22—C23 | 122.8 (4) |
C6—N2—C7 | 113.7 (3) | N5—C23—C22 | 110.3 (3) |
C6—N2—C13 | 110.9 (3) | N5—C23—H22 | 109.3 |
C7—N2—C13 | 109.0 (3) | N5—C23—H23 | 109.3 |
Cu1—N3—C8 | 113.2 (3) | C22—C23—H22 | 109.3 |
Cu1—N3—C12 | 126.9 (3) | C22—C23—H23 | 109.3 |
C8—N3—C12 | 119.9 (4) | H22—C23—H23 | 109.5 |
Cu2—N4—C18 | 127.5 (3) | N5—C24—C25 | 108.9 (3) |
Cu2—N4—C22 | 113.8 (3) | N5—C24—H24 | 109.6 |
C18—N4—C22 | 118.6 (3) | N5—C24—H25 | 109.6 |
Cu2—N5—C23 | 105.0 (2) | C25—C24—H24 | 109.6 |
Cu2—N5—C24 | 106.0 (2) | C25—C24—H25 | 109.6 |
Cu2—N5—C30 | 111.4 (2) | H24—C24—H25 | 109.5 |
C23—N5—C24 | 113.0 (3) | N6—C25—C24 | 116.4 (3) |
C23—N5—C30 | 112.3 (3) | N6—C25—C26 | 120.4 (4) |
C24—N5—C30 | 108.9 (3) | C24—C25—C26 | 123.1 (4) |
Cu2—N6—C25 | 113.2 (3) | C25—C26—C27 | 119.2 (4) |
Cu2—N6—C29 | 126.7 (3) | C25—C26—H26 | 120.4 |
C25—N6—C29 | 120.0 (3) | C27—C26—H26 | 120.4 |
N1—C1—C2 | 122.6 (4) | C26—C27—C28 | 119.4 (4) |
N1—C1—H1 | 118.7 | C26—C27—H27 | 120.3 |
C2—C1—H1 | 118.7 | C28—C27—H27 | 120.3 |
C1—C2—C3 | 118.5 (4) | C27—C28—C29 | 119.4 (4) |
C1—C2—H2 | 120.7 | C27—C28—H28 | 120.3 |
C3—C2—H2 | 120.7 | C29—C28—H28 | 120.3 |
C2—C3—C4 | 119.7 (4) | N6—C29—C28 | 121.6 (4) |
C2—C3—H3 | 120.2 | N6—C29—H29 | 119.2 |
C4—C3—H3 | 120.2 | C28—C29—H29 | 119.2 |
C3—C4—C5 | 118.7 (4) | N5—C30—C31 | 113.6 (3) |
C3—C4—H4 | 120.7 | N5—C30—H30 | 108.4 |
C5—C4—H4 | 120.7 | N5—C30—H31 | 108.4 |
N1—C5—C4 | 121.7 (3) | C31—C30—H30 | 108.4 |
N1—C5—C6 | 115.6 (3) | C31—C30—H31 | 108.4 |
C4—C5—C6 | 122.6 (3) | H30—C30—H31 | 109.5 |
N2—C6—C5 | 110.5 (3) | O2—C31—C30 | 115.1 (4) |
N2—C6—H5 | 109.2 | O2—C31—C32 | 109.6 (4) |
N2—C6—H6 | 109.2 | C30—C31—C32 | 135.3 (4) |
C5—C6—H5 | 109.2 | C31—C32—C33 | 106.1 (5) |
C5—C6—H6 | 109.2 | C31—C32—H32 | 127.0 |
H5—C6—H6 | 109.5 | C33—C32—H32 | 127.0 |
N2—C7—C8 | 108.1 (3) | C32—C33—C34 | 107.1 (5) |
N2—C7—H7 | 109.8 | C32—C33—H33 | 126.4 |
N2—C7—H8 | 109.8 | C34—C33—H33 | 126.4 |
C8—C7—H7 | 109.8 | O2—C34—C33 | 110.6 (5) |
C8—C7—H8 | 109.8 | O2—C34—H34 | 124.7 |
H7—C7—H8 | 109.5 | C33—C34—H34 | 124.7 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) x, y−1, z; (v) −x+2, −y+1, −z; (vi) −x+1, −y, −z; (vii) x, y−1, z−1; (viii) −x+2, −y+1, −z+1; (ix) x+1, y, z+1; (x) x, y, z+1. |
Crystal data top
[Cu(C14H17N3O)Cl][CuCl4]0.5 | Dx = 1.720 Mg m−3 |
Mr = 444.99 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, C2/c | Cell parameters from 25 reflections |
a = 23.377 (4) Å | θ = 10–15° |
b = 9.204 (2) Å | µ = 2.34 mm−1 |
c = 16.361 (3) Å | T = 295 K |
β = 102.43 (1)° | Plate, dark blue |
V = 3437.8 (10) Å3 | 0.6 × 0.5 × 0.4 mm |
Z = 8 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.041 |
θ–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→30 |
Tmin = 0.331, Tmax = 0.446 | k = 0→12 |
4290 measured reflections | l = −21→21 |
3943 independent reflections | 3 standard reflections every 100 reflections |
3182 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.131 | (Δ/σ)max = 0.026 |
S = 1.00 | Δρmax = 0.51 e Å−3 |
3943 reflections | Δρmin = −0.86 e Å−3 |
207 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.16739 (2) | −0.34527 (4) | 0.44410 (2) | 0.03629 (9) | |
Cu2 | 0.0000 | 0.14495 (5) | 0.2500 | 0.0433 (1) | |
Cl1 | 0.23894 (4) | −0.4717 (1) | 0.40455 (6) | 0.0664 (3) | |
Cl2 | 0.04792 (4) | −0.01008 (9) | 0.18383 (6) | 0.0505 (2) | |
Cl3 | 0.02483 (5) | 0.3064 (1) | 0.35798 (9) | 0.0771 (3) | |
O1 | 0.08743 (10) | −0.4067 (3) | 0.3406 (1) | 0.0459 (6) | |
N1 | 0.1777 (1) | −0.1594 (3) | 0.3872 (2) | 0.0433 (6) | |
N2 | 0.1054 (1) | −0.2297 (3) | 0.4882 (1) | 0.0370 (6) | |
N3 | 0.1579 (1) | −0.4811 (3) | 0.5357 (1) | 0.0384 (6) | |
C1 | 0.2114 (2) | −0.1383 (4) | 0.3306 (2) | 0.0544 (9) | |
C2 | 0.2169 (2) | −0.0066 (5) | 0.2952 (2) | 0.067 (1) | |
C3 | 0.1884 (2) | 0.1106 (5) | 0.3186 (3) | 0.070 (1) | |
C4 | 0.1530 (2) | 0.0919 (4) | 0.3759 (2) | 0.0588 (10) | |
C5 | 0.1482 (1) | −0.0459 (4) | 0.4088 (2) | 0.0444 (7) | |
C6 | 0.1109 (2) | −0.0725 (4) | 0.4712 (2) | 0.0515 (9) | |
C7 | 0.1170 (1) | −0.2617 (4) | 0.5791 (2) | 0.0427 (7) | |
C8 | 0.1301 (1) | −0.4214 (3) | 0.5918 (2) | 0.0388 (7) | |
C9 | 0.1156 (1) | −0.5015 (4) | 0.6554 (2) | 0.0497 (8) | |
C10 | 0.1297 (2) | −0.6470 (4) | 0.6623 (2) | 0.0556 (9) | |
C11 | 0.1584 (2) | −0.7077 (4) | 0.6058 (2) | 0.0554 (10) | |
C12 | 0.1722 (2) | −0.6226 (4) | 0.5433 (2) | 0.0480 (8) | |
C13 | 0.0463 (1) | −0.2871 (4) | 0.4459 (2) | 0.0422 (7) | |
C14 | 0.0426 (1) | −0.3085 (4) | 0.3536 (2) | 0.0465 (8) | |
H1 | 0.073 (2) | −0.502 (2) | 0.348 (3) | 0.0714* | |
H2 | 0.2324 | −0.2196 | 0.3148 | 0.0653* | |
H3 | 0.2406 | 0.0038 | 0.2543 | 0.0806* | |
H4 | 0.1928 | 0.2049 | 0.2957 | 0.0838* | |
H5 | 0.1321 | 0.1727 | 0.3925 | 0.0705* | |
H6 | 0.0726 | −0.0333 | 0.4496 | 0.0619* | |
H7 | 0.1283 | −0.0244 | 0.5226 | 0.0619* | |
H8 | 0.1499 | −0.2058 | 0.6077 | 0.0512* | |
H9 | 0.0832 | −0.2373 | 0.6007 | 0.0512* | |
H10 | 0.0959 | −0.4564 | 0.6945 | 0.0596* | |
H11 | 0.1196 | −0.7049 | 0.7059 | 0.0667* | |
H12 | 0.1688 | −0.8088 | 0.6098 | 0.0665* | |
H13 | 0.1926 | −0.6655 | 0.5043 | 0.0576* | |
H14 | 0.0398 | −0.3786 | 0.4706 | 0.0507* | |
H15 | 0.0168 | −0.2192 | 0.4535 | 0.0507* | |
H16 | 0.0476 | −0.2166 | 0.3283 | 0.0558* | |
H17 | 0.0049 | −0.3479 | 0.3283 | 0.0558* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0339 (2) | 0.0451 (2) | 0.0347 (2) | 0.0036 (1) | 0.0180 (1) | −0.0012 (1) |
Cu2 | 0.0406 (3) | 0.0293 (2) | 0.0645 (4) | 0.0000 | 0.0212 (3) | 0.0000 |
Cl1 | 0.0593 (5) | 0.0875 (7) | 0.0635 (5) | 0.0276 (5) | 0.0380 (4) | 0.0041 (5) |
Cl2 | 0.0553 (4) | 0.0391 (4) | 0.0642 (5) | −0.0014 (3) | 0.0284 (4) | −0.0048 (3) |
Cl3 | 0.0633 (6) | 0.0598 (6) | 0.1180 (9) | −0.0185 (5) | 0.0412 (6) | −0.0426 (6) |
O1 | 0.046 (1) | 0.053 (1) | 0.042 (1) | −0.0011 (9) | 0.0158 (8) | −0.0045 (10) |
N1 | 0.042 (1) | 0.053 (1) | 0.038 (1) | −0.011 (1) | 0.015 (1) | −0.001 (1) |
N2 | 0.038 (1) | 0.040 (1) | 0.037 (1) | 0.0035 (9) | 0.0163 (9) | 0.0001 (9) |
N3 | 0.038 (1) | 0.045 (1) | 0.035 (1) | 0.0046 (10) | 0.0125 (9) | −0.0015 (9) |
C1 | 0.050 (2) | 0.079 (2) | 0.038 (2) | −0.018 (2) | 0.016 (1) | −0.002 (1) |
C2 | 0.066 (2) | 0.091 (2) | 0.046 (2) | −0.031 (2) | 0.016 (2) | 0.010 (2) |
C3 | 0.077 (3) | 0.070 (2) | 0.060 (2) | −0.025 (2) | 0.007 (2) | 0.024 (2) |
C4 | 0.064 (2) | 0.049 (2) | 0.059 (2) | −0.009 (2) | 0.004 (1) | 0.009 (2) |
C5 | 0.044 (2) | 0.047 (1) | 0.042 (1) | −0.011 (1) | 0.007 (1) | −0.001 (1) |
C6 | 0.059 (2) | 0.041 (1) | 0.061 (2) | 0.000 (1) | 0.029 (2) | −0.001 (1) |
C7 | 0.047 (2) | 0.049 (1) | 0.035 (1) | 0.003 (1) | 0.018 (1) | −0.005 (1) |
C8 | 0.035 (1) | 0.051 (1) | 0.033 (1) | 0.004 (1) | 0.012 (1) | 0.000 (1) |
C9 | 0.045 (2) | 0.066 (2) | 0.041 (2) | 0.007 (1) | 0.017 (1) | 0.012 (1) |
C10 | 0.048 (2) | 0.065 (2) | 0.054 (2) | 0.002 (1) | 0.012 (1) | 0.018 (2) |
C11 | 0.059 (2) | 0.045 (2) | 0.061 (2) | 0.003 (2) | 0.009 (1) | 0.007 (1) |
C12 | 0.050 (2) | 0.048 (1) | 0.047 (2) | 0.008 (1) | 0.011 (1) | −0.006 (1) |
C13 | 0.036 (1) | 0.050 (2) | 0.044 (1) | 0.006 (1) | 0.015 (1) | 0.005 (1) |
C14 | 0.043 (2) | 0.052 (2) | 0.044 (1) | 0.003 (1) | 0.007 (1) | 0.003 (1) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.244 (1) | C3—H4 | 0.960 |
Cu1—O1 | 2.306 (2) | C4—C5 | 1.392 (5) |
Cu1—N1 | 1.987 (3) | C4—H5 | 0.960 |
Cu1—N2 | 2.050 (2) | C5—C6 | 1.498 (4) |
Cu1—N3 | 2.001 (3) | C6—H6 | 0.960 |
Cu2—Cl2i | 2.233 (1) | C6—H7 | 0.960 |
Cu2—Cl2 | 2.233 (1) | C7—C8 | 1.507 (4) |
Cu2—Cl3i | 2.286 (1) | C7—H8 | 0.960 |
Cu2—Cl3 | 2.286 (1) | C7—H9 | 0.960 |
O1—C14 | 1.434 (4) | C8—C9 | 1.375 (4) |
O1—H1 | 0.958 (8) | C9—C10 | 1.378 (5) |
N1—C1 | 1.352 (4) | C9—H10 | 0.960 |
N1—C5 | 1.340 (4) | C10—C11 | 1.373 (6) |
N2—C6 | 1.485 (4) | C10—H11 | 0.960 |
N2—C7 | 1.482 (4) | C11—C12 | 1.380 (5) |
N2—C13 | 1.501 (4) | C11—H12 | 0.960 |
N3—C8 | 1.349 (4) | C12—H13 | 0.960 |
N3—C12 | 1.344 (4) | C13—C14 | 1.507 (4) |
C1—C2 | 1.362 (6) | C13—H14 | 0.960 |
C1—H2 | 0.960 | C13—H15 | 0.960 |
C2—C3 | 1.365 (7) | C14—H16 | 0.960 |
C2—H3 | 0.960 | C14—H17 | 0.960 |
C3—C4 | 1.388 (6) | | |
| | | |
Cl1···C5ii | 3.583 (3) | N3···C1ii | 3.529 (4) |
Cl2···C14i | 3.440 (3) | N3···C2ii | 3.570 (5) |
Cl3···O1iii | 3.061 (3) | C1···C10iv | 3.588 (5) |
Cl3···C4 | 3.546 (4) | C2···C12ii | 3.487 (5) |
Cl3···C14iii | 3.571 (4) | C3···C12ii | 3.544 (6) |
O1···C10iv | 3.312 (4) | C9···H1v | 3.51 (4) |
O1···C9iv | 3.347 (4) | C14···C14i | 3.542 (6) |
| | | |
Cl1—Cu1—O1 | 101.4 (1) | N1—C5—C4 | 121.3 (3) |
Cl1—Cu1—N1 | 97.9 (1) | N1—C5—C6 | 117.4 (3) |
Cl1—Cu1—N2 | 176.2 (1) | C4—C5—C6 | 121.3 (3) |
Cl1—Cu1—N3 | 95.9 (1) | N2—C6—C5 | 112.0 (3) |
O1—Cu1—N1 | 91.6 (1) | N2—C6—H6 | 108.8 |
O1—Cu1—N2 | 82.1 (1) | N2—C6—H7 | 108.8 |
O1—Cu1—N3 | 101.2 (1) | C5—C6—H6 | 108.9 |
N1—Cu1—N2 | 83.4 (1) | C5—C6—H7 | 108.9 |
N1—Cu1—N3 | 159.0 (1) | H6—C6—H7 | 109.5 |
N2—Cu1—N3 | 81.9 (1) | N2—C7—C8 | 108.7 (2) |
Cl2—Cu2—Cl2i | 100.6 (1) | N2—C7—H8 | 109.7 |
Cl2—Cu2—Cl3 | 136.0 (1) | N2—C7—H9 | 109.7 |
Cl2—Cu2—Cl3i | 96.4 (1) | C8—C7—H8 | 109.7 |
Cl2i—Cu2—Cl3 | 96.4 (1) | C8—C7—H9 | 109.7 |
Cl2i—Cu2—Cl3i | 136.0 (1) | H8—C7—H9 | 109.5 |
Cl3—Cu2—Cl3i | 98.9 (1) | N3—C8—C7 | 114.6 (2) |
Cu1—O1—C14 | 103.9 (2) | N3—C8—C9 | 121.9 (3) |
Cu1—O1—H1 | 112 (2) | C7—C8—C9 | 123.5 (3) |
C14—O1—H1 | 105 (2) | C8—C9—C10 | 119.4 (3) |
Cu1—N1—C1 | 126.3 (3) | C8—C9—H10 | 120.3 |
Cu1—N1—C5 | 115.2 (2) | C10—C9—H10 | 120.3 |
C1—N1—C5 | 118.5 (3) | C9—C10—C11 | 118.8 (3) |
Cu1—N2—C6 | 110.1 (2) | C9—C10—H11 | 120.6 |
Cu1—N2—C7 | 105.1 (2) | C11—C10—H11 | 120.6 |
Cu1—N2—C13 | 107.8 (2) | C10—C11—C12 | 119.6 (3) |
C6—N2—C7 | 112.2 (2) | C10—C11—H12 | 120.2 |
C6—N2—C13 | 111.4 (2) | C12—C11—H12 | 120.2 |
C7—N2—C13 | 110.1 (2) | N3—C12—C11 | 121.6 (3) |
Cu1—N3—C8 | 113.7 (2) | N3—C12—H13 | 119.2 |
Cu1—N3—C12 | 127.5 (2) | C11—C12—H13 | 119.2 |
C8—N3—C12 | 118.6 (3) | N2—C13—C14 | 111.0 (2) |
N1—C1—C2 | 122.8 (4) | N2—C13—H14 | 109.1 |
N1—C1—H2 | 118.6 | N2—C13—H15 | 109.1 |
C2—C1—H2 | 118.6 | C14—C13—H14 | 109.1 |
C1—C2—C3 | 119.1 (3) | C14—C13—H15 | 109.1 |
C1—C2—H3 | 120.4 | H14—C13—H15 | 109.5 |
C3—C2—H3 | 120.4 | O1—C14—C13 | 110.1 (2) |
C2—C3—C4 | 119.3 (4) | O1—C14—H16 | 109.3 |
C2—C3—H4 | 120.3 | O1—C14—H17 | 109.3 |
C4—C3—H4 | 120.3 | C13—C14—H16 | 109.3 |
C3—C4—C5 | 118.9 (4) | C13—C14—H17 | 109.3 |
C3—C4—H5 | 120.6 | H16—C14—H17 | 109.5 |
C5—C4—H5 | 120.6 | | |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y−1/2, −z+1; (iii) x, y+1, z; (iv) x, −y−1, z−1/2; (v) x, −y−1, z+1/2. |
Crystal data top
[Cu(C18H24N4O)Cl]ClO4 | Dx = 1.599 Mg m−3 |
Mr = 510.86 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/n | Cell parameters from 25 reflections |
a = 9.282 (3) Å | θ = 10–15° |
b = 11.592 (4) Å | µ = 1.32 mm−1 |
c = 19.731 (3) Å | T = 299 K |
β = 90.76 (2)° | Prism, blue |
V = 2122.8 (9) Å3 | 0.6 × 0.3 × 0.2 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.015 |
θ–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→12 |
Tmin = 0.638, Tmax = 0.799 | k = 0→15 |
5433 measured reflections | l = −26→26 |
4878 independent reflections | 3 standard reflections every 100 reflections |
3479 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.197 | (Δ/σ)max = 0.011 |
S = 1.32 | Δρmax = 0.59 e Å−3 |
4878 reflections | Δρmin = −0.48 e Å−3 |
271 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.29803 (6) | 0.14321 (5) | 0.42748 (3) | 0.0326 (2) | |
Cl1 | 0.1413 (1) | −0.0017 (1) | 0.41111 (7) | 0.0514 (4) | |
Cl2 | 0.3531 (2) | 0.4078 (1) | 0.68156 (7) | 0.0512 (4) | |
O1 | −0.1291 (4) | 0.3132 (4) | 0.4439 (2) | 0.065 (1) | |
O2 | 0.2571 (8) | 0.3365 (7) | 0.6442 (3) | 0.118 (3) | |
O3 | 0.285 (1) | 0.5102 (6) | 0.6981 (4) | 0.150 (3) | |
O4 | 0.3898 (8) | 0.3430 (6) | 0.7394 (3) | 0.112 (2) | |
O5 | 0.4689 (8) | 0.4197 (7) | 0.6368 (3) | 0.126 (3) | |
N1 | 0.3453 (4) | 0.1664 (3) | 0.3302 (2) | 0.039 (1) | |
N2 | 0.4797 (4) | 0.2418 (3) | 0.4439 (2) | 0.0344 (9) | |
N3 | 0.3263 (4) | 0.1119 (3) | 0.5265 (2) | 0.038 (1) | |
N4 | 0.1802 (4) | 0.3274 (3) | 0.4293 (2) | 0.038 (1) | |
C1 | 0.2587 (6) | 0.1399 (5) | 0.2763 (3) | 0.052 (2) | |
C2 | 0.2947 (8) | 0.1702 (7) | 0.2114 (3) | 0.067 (2) | |
C3 | 0.4207 (9) | 0.2306 (8) | 0.2008 (3) | 0.086 (3) | |
C4 | 0.5110 (7) | 0.2564 (7) | 0.2551 (3) | 0.069 (2) | |
C5 | 0.4681 (5) | 0.2238 (4) | 0.3193 (2) | 0.041 (1) | |
C6 | 0.5635 (5) | 0.2470 (4) | 0.3801 (3) | 0.041 (1) | |
C7 | 0.5619 (5) | 0.1861 (4) | 0.5004 (3) | 0.041 (1) | |
C8 | 0.4590 (5) | 0.1377 (4) | 0.5511 (2) | 0.037 (1) | |
C9 | 0.4974 (6) | 0.1153 (5) | 0.6178 (3) | 0.048 (1) | |
C10 | 0.3954 (7) | 0.0688 (5) | 0.6608 (3) | 0.054 (2) | |
C11 | 0.2596 (6) | 0.0439 (5) | 0.6355 (3) | 0.052 (2) | |
C12 | 0.2291 (5) | 0.0660 (4) | 0.5690 (3) | 0.042 (1) | |
C13 | 0.4324 (5) | 0.3586 (4) | 0.4660 (3) | 0.041 (1) | |
C14 | 0.3075 (5) | 0.4028 (4) | 0.4237 (3) | 0.044 (1) | |
C15 | 0.1074 (6) | 0.3469 (5) | 0.4948 (3) | 0.048 (1) | |
C16 | −0.0325 (6) | 0.2807 (6) | 0.4976 (3) | 0.061 (2) | |
C17 | −0.0613 (6) | 0.2893 (6) | 0.3809 (3) | 0.060 (2) | |
C18 | 0.0754 (5) | 0.3563 (5) | 0.3747 (3) | 0.048 (1) | |
H1 | 0.1703 | 0.0991 | 0.2838 | 0.0630* | |
H2 | 0.2330 | 0.1496 | 0.1739 | 0.0807* | |
H3 | 0.4457 | 0.2544 | 0.1559 | 0.1039* | |
H4 | 0.6008 | 0.2958 | 0.2485 | 0.0827* | |
H5 | 0.6054 | 0.3223 | 0.3758 | 0.0492* | |
H6 | 0.6386 | 0.1901 | 0.3820 | 0.0492* | |
H7 | 0.6200 | 0.1249 | 0.4826 | 0.0496* | |
H8 | 0.6229 | 0.2423 | 0.5221 | 0.0496* | |
H9 | 0.5931 | 0.1317 | 0.6342 | 0.0580* | |
H10 | 0.4192 | 0.0540 | 0.7075 | 0.0651* | |
H11 | 0.1877 | 0.0115 | 0.6644 | 0.0620* | |
H12 | 0.1345 | 0.0482 | 0.5516 | 0.0503* | |
H13 | 0.4035 | 0.3546 | 0.5125 | 0.0498* | |
H14 | 0.5117 | 0.4111 | 0.4619 | 0.0498* | |
H15 | 0.3358 | 0.4061 | 0.3771 | 0.0525* | |
H16 | 0.2827 | 0.4789 | 0.4389 | 0.0525* | |
H17 | 0.1696 | 0.3218 | 0.5311 | 0.0582* | |
H18 | 0.0877 | 0.4277 | 0.4998 | 0.0582* | |
H19 | −0.0776 | 0.2958 | 0.5402 | 0.0736* | |
H20 | −0.0122 | 0.1997 | 0.4939 | 0.0736* | |
H21 | −0.0401 | 0.2083 | 0.3783 | 0.0718* | |
H22 | −0.1256 | 0.3101 | 0.3443 | 0.0718* | |
H23 | 0.0536 | 0.4371 | 0.3770 | 0.0579* | |
H24 | 0.1179 | 0.3392 | 0.3317 | 0.0579* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0274 (3) | 0.0329 (3) | 0.0376 (3) | −0.0049 (2) | 0.0009 (2) | −0.0011 (2) |
Cl1 | 0.0420 (7) | 0.0484 (7) | 0.0638 (8) | −0.0182 (5) | 0.0033 (6) | −0.0059 (6) |
Cl2 | 0.0669 (9) | 0.0443 (7) | 0.0424 (7) | −0.0011 (6) | 0.0020 (6) | 0.0027 (5) |
O1 | 0.033 (2) | 0.099 (3) | 0.062 (2) | 0.012 (2) | 0.004 (2) | 0.013 (2) |
O2 | 0.132 (6) | 0.134 (6) | 0.089 (4) | −0.037 (4) | −0.033 (4) | −0.013 (4) |
O3 | 0.26 (1) | 0.071 (4) | 0.116 (5) | 0.054 (5) | 0.058 (6) | 0.001 (4) |
O4 | 0.134 (6) | 0.123 (6) | 0.080 (4) | 0.018 (4) | −0.012 (4) | 0.039 (4) |
O5 | 0.120 (5) | 0.150 (7) | 0.109 (5) | −0.006 (5) | 0.050 (4) | 0.036 (5) |
N1 | 0.036 (2) | 0.040 (2) | 0.040 (2) | −0.001 (2) | 0.001 (2) | −0.003 (2) |
N2 | 0.028 (2) | 0.031 (2) | 0.044 (2) | −0.001 (1) | 0.000 (1) | 0.001 (2) |
N3 | 0.035 (2) | 0.033 (2) | 0.048 (2) | 0.001 (2) | 0.003 (2) | 0.003 (2) |
N4 | 0.031 (2) | 0.037 (2) | 0.047 (2) | 0.006 (2) | 0.001 (2) | 0.002 (2) |
C1 | 0.048 (3) | 0.062 (4) | 0.047 (3) | −0.007 (3) | −0.003 (2) | −0.011 (3) |
C2 | 0.077 (4) | 0.085 (5) | 0.039 (3) | −0.012 (4) | −0.008 (3) | −0.008 (3) |
C3 | 0.096 (6) | 0.125 (7) | 0.038 (3) | −0.030 (5) | 0.006 (3) | 0.003 (4) |
C4 | 0.071 (4) | 0.091 (5) | 0.046 (3) | −0.024 (4) | 0.012 (3) | −0.003 (3) |
C5 | 0.040 (2) | 0.043 (3) | 0.040 (2) | −0.001 (2) | 0.004 (2) | −0.001 (2) |
C6 | 0.032 (2) | 0.045 (3) | 0.046 (3) | −0.005 (2) | 0.002 (2) | 0.000 (2) |
C7 | 0.030 (2) | 0.042 (3) | 0.051 (3) | 0.000 (2) | −0.007 (2) | 0.005 (2) |
C8 | 0.036 (2) | 0.035 (2) | 0.040 (2) | 0.001 (2) | −0.003 (2) | 0.001 (2) |
C9 | 0.048 (3) | 0.051 (3) | 0.046 (3) | 0.005 (2) | −0.008 (2) | 0.001 (2) |
C10 | 0.070 (4) | 0.056 (3) | 0.038 (3) | 0.005 (3) | 0.000 (2) | 0.007 (2) |
C11 | 0.057 (3) | 0.045 (3) | 0.053 (3) | 0.001 (2) | 0.017 (2) | 0.007 (2) |
C12 | 0.034 (2) | 0.042 (3) | 0.050 (3) | 0.000 (2) | 0.005 (2) | 0.004 (2) |
C13 | 0.039 (2) | 0.031 (2) | 0.054 (3) | −0.004 (2) | −0.006 (2) | −0.007 (2) |
C14 | 0.043 (3) | 0.030 (2) | 0.058 (3) | 0.002 (2) | −0.004 (2) | 0.002 (2) |
C15 | 0.050 (3) | 0.053 (3) | 0.042 (3) | 0.019 (2) | 0.001 (2) | −0.003 (2) |
C16 | 0.044 (3) | 0.089 (5) | 0.051 (3) | 0.011 (3) | 0.008 (2) | 0.014 (3) |
C17 | 0.039 (3) | 0.087 (5) | 0.054 (3) | 0.007 (3) | −0.006 (2) | 0.010 (3) |
C18 | 0.037 (2) | 0.059 (3) | 0.048 (3) | 0.011 (2) | 0.001 (2) | 0.007 (3) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.243 (1) | C5—C6 | 1.506 (7) |
Cu1—N1 | 1.993 (4) | C6—H5 | 0.960 |
Cu1—N2 | 2.059 (4) | C6—H6 | 0.960 |
Cu1—N3 | 2.000 (4) | C7—C8 | 1.501 (7) |
Cu1—N4 | 2.399 (4) | C7—H7 | 0.960 |
Cl2—O2 | 1.416 (6) | C7—H8 | 0.960 |
Cl2—O3 | 1.385 (6) | C8—C9 | 1.384 (7) |
Cl2—O4 | 1.404 (5) | C9—C10 | 1.388 (8) |
Cl2—O5 | 1.407 (6) | C9—H9 | 0.960 |
O1—C16 | 1.429 (7) | C10—C11 | 1.380 (8) |
O1—C17 | 1.429 (7) | C10—H10 | 0.961 |
N1—C1 | 1.359 (7) | C11—C12 | 1.364 (7) |
N1—C5 | 1.339 (6) | C11—H11 | 0.960 |
N2—C6 | 1.490 (6) | C12—H12 | 0.960 |
N2—C7 | 1.489 (6) | C13—C14 | 1.509 (7) |
N2—C13 | 1.490 (6) | C13—H13 | 0.960 |
N3—C8 | 1.352 (6) | C13—H14 | 0.960 |
N3—C12 | 1.349 (6) | C14—H15 | 0.960 |
N4—C14 | 1.475 (6) | C14—H16 | 0.960 |
N4—C15 | 1.483 (6) | C15—C16 | 1.510 (9) |
N4—C18 | 1.481 (6) | C15—H17 | 0.960 |
C1—C2 | 1.372 (8) | C15—H18 | 0.960 |
C1—H1 | 0.961 | C16—H19 | 0.960 |
C2—C3 | 1.381 (10) | C16—H20 | 0.960 |
C2—H2 | 0.960 | C17—C18 | 1.494 (8) |
C3—C4 | 1.386 (10) | C17—H21 | 0.960 |
C3—H3 | 0.960 | C17—H22 | 0.960 |
C4—C5 | 1.385 (7) | C18—H23 | 0.960 |
C4—H4 | 0.960 | C18—H24 | 0.960 |
| | | |
Cl1···C12i | 3.544 (5) | O3···C10iv | 3.340 (8) |
O1···C6ii | 3.197 (6) | O3···C4v | 3.42 (1) |
O1···C7ii | 3.423 (6) | O3···C17vi | 3.474 (10) |
O2···C15 | 3.244 (8) | O3···C6v | 3.511 (9) |
O2···C4iii | 3.361 (10) | O4···C17vii | 3.212 (8) |
O2···C10 | 3.37 (1) | O4···C1vii | 3.497 (9) |
O2···C11 | 3.395 (9) | O4···C10 | 3.538 (9) |
O2···C3iii | 3.42 (1) | O5···C14v | 3.167 (8) |
O2···C9 | 3.44 (1) | O5···C13v | 3.407 (8) |
O2···C12 | 3.477 (9) | O5···C13 | 3.457 (9) |
O2···C8 | 3.505 (9) | O5···C2vii | 3.50 (1) |
O2···N3 | 3.553 (8) | O5···C9 | 3.56 (1) |
O3···C11iv | 3.338 (9) | C6···C17viii | 3.517 (7) |
| | | |
Cl1—Cu1—N1 | 96.5 (1) | N2—C7—H7 | 109.4 |
Cl1—Cu1—N2 | 165.2 (1) | N2—C7—H8 | 109.4 |
Cl1—Cu1—N3 | 94.7 (1) | C8—C7—H7 | 109.4 |
Cl1—Cu1—N4 | 111.9 (1) | C8—C7—H8 | 109.4 |
N1—Cu1—N2 | 83.5 (2) | H7—C7—H8 | 109.5 |
N1—Cu1—N3 | 159.6 (2) | N3—C8—C7 | 115.3 (4) |
N1—Cu1—N4 | 90.0 (1) | N3—C8—C9 | 121.5 (4) |
N2—Cu1—N3 | 81.4 (2) | C7—C8—C9 | 123.1 (4) |
N2—Cu1—N4 | 82.9 (1) | C8—C9—C10 | 119.0 (5) |
N3—Cu1—N4 | 101.6 (1) | C8—C9—H9 | 120.5 |
O2—Cl2—O3 | 109.8 (6) | C10—C9—H9 | 120.5 |
O2—Cl2—O4 | 104.8 (4) | C9—C10—C11 | 119.2 (5) |
O2—Cl2—O5 | 102.2 (5) | C9—C10—H10 | 120.4 |
O3—Cl2—O4 | 111.9 (4) | C11—C10—H10 | 120.4 |
O3—Cl2—O5 | 114.6 (5) | C10—C11—C12 | 119.1 (5) |
O4—Cl2—O5 | 112.5 (4) | C10—C11—H11 | 120.5 |
C16—O1—C17 | 108.4 (4) | C12—C11—H11 | 120.5 |
Cu1—N1—C1 | 126.0 (4) | N3—C12—C11 | 122.7 (5) |
Cu1—N1—C5 | 114.8 (3) | N3—C12—H12 | 118.6 |
C1—N1—C5 | 118.9 (4) | C11—C12—H12 | 118.7 |
Cu1—N2—C6 | 109.0 (3) | N2—C13—C14 | 112.0 (4) |
Cu1—N2—C7 | 106.7 (3) | N2—C13—H13 | 108.8 |
Cu1—N2—C13 | 107.8 (3) | N2—C13—H14 | 108.8 |
C6—N2—C7 | 112.4 (4) | C14—C13—H13 | 108.8 |
C6—N2—C13 | 111.7 (4) | C14—C13—H14 | 108.8 |
C7—N2—C13 | 109.0 (4) | H13—C13—H14 | 109.5 |
Cu1—N3—C8 | 114.7 (3) | N4—C14—C13 | 111.5 (4) |
Cu1—N3—C12 | 126.7 (3) | N4—C14—H15 | 109.0 |
C8—N3—C12 | 118.5 (4) | N4—C14—H16 | 109.0 |
Cu1—N4—C14 | 99.2 (3) | C13—C14—H15 | 109.0 |
Cu1—N4—C15 | 111.2 (3) | C13—C14—H16 | 108.9 |
Cu1—N4—C18 | 119.0 (3) | H15—C14—H16 | 109.5 |
C14—N4—C15 | 110.5 (4) | N4—C15—C16 | 110.9 (5) |
C14—N4—C18 | 109.3 (4) | N4—C15—H17 | 109.1 |
C15—N4—C18 | 107.3 (4) | N4—C15—H18 | 109.1 |
N1—C1—C2 | 121.5 (5) | C16—C15—H17 | 109.1 |
N1—C1—H1 | 119.2 | C16—C15—H18 | 109.1 |
C2—C1—H1 | 119.2 | H17—C15—H18 | 109.5 |
C1—C2—C3 | 119.3 (6) | O1—C16—C15 | 111.7 (5) |
C1—C2—H2 | 120.4 | O1—C16—H19 | 108.9 |
C3—C2—H2 | 120.4 | O1—C16—H20 | 108.9 |
C2—C3—C4 | 119.8 (6) | C15—C16—H19 | 108.9 |
C2—C3—H3 | 120.2 | C15—C16—H20 | 108.9 |
C4—C3—H3 | 120.0 | H19—C16—H20 | 109.4 |
C3—C4—C5 | 118.0 (6) | O1—C17—C18 | 110.8 (5) |
C3—C4—H4 | 121.0 | O1—C17—H21 | 109.2 |
C5—C4—H4 | 121.0 | O1—C17—H22 | 109.2 |
N1—C5—C4 | 122.5 (5) | C18—C17—H21 | 109.2 |
N1—C5—C6 | 117.0 (4) | C18—C17—H22 | 109.2 |
C4—C5—C6 | 120.4 (5) | H21—C17—H22 | 109.4 |
N2—C6—C5 | 111.0 (4) | N4—C18—C17 | 111.9 (4) |
N2—C6—H5 | 109.1 | N4—C18—H23 | 108.8 |
N2—C6—H6 | 109.1 | N4—C18—H24 | 108.8 |
C5—C6—H5 | 109.1 | C17—C18—H23 | 108.9 |
C5—C6—H6 | 109.1 | C17—C18—H24 | 108.9 |
H5—C6—H6 | 109.4 | H23—C18—H24 | 109.5 |
N2—C7—C8 | 109.6 (4) | | |
Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1; (vii) x+1/2, −y+1/2, z+1/2; (viii) x+1, y, z. |
Crystal data top
[Cu(C19H26N4)Cl]PF6 | Dx = 1.599 Mg m−3 |
Mr = 554.41 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/c | Cell parameters from 25 reflections |
a = 11.855 (3) Å | θ = 10–15° |
b = 15.258 (2) Å | µ = 1.20 mm−1 |
c = 13.186 (3) Å | T = 299 K |
β = 105.14 (2)° | Prism, blue |
V = 2302.2 (7) Å3 | 0.6 × 0.3 × 0.3 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.026 |
θ–2θ scans | θmax = 25.0° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→14 |
Tmin = 0.654, Tmax = 0.717 | k = 0→18 |
4439 measured reflections | l = −15→15 |
4048 independent reflections | 3 standard reflections every 100 reflections |
2903 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.147 | (Δ/σ)max = 0.002 |
S = 0.99 | Δρmax = 0.33 e Å−3 |
4048 reflections | Δρmin = −0.27 e Å−3 |
289 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.85260 (4) | 0.07907 (3) | 0.00216 (4) | 0.0493 (2) | |
Cl1 | 0.9661 (1) | 0.15244 (9) | −0.0808 (1) | 0.0729 (4) | |
P1 | 0.3561 (1) | 0.13326 (8) | −0.37571 (10) | 0.0655 (4) | |
F1 | 0.2400 (4) | 0.0775 (3) | −0.4051 (4) | 0.137 (2) | |
F2 | 0.3049 (4) | 0.2016 (3) | −0.4638 (4) | 0.153 (2) | |
F3 | 0.3086 (4) | 0.1851 (3) | −0.2936 (4) | 0.150 (2) | |
F4 | 0.4062 (3) | 0.0630 (3) | −0.2877 (3) | 0.107 (1) | |
F5 | 0.4700 (3) | 0.1899 (3) | −0.3446 (3) | 0.112 (1) | |
F6 | 0.4120 (5) | 0.0785 (3) | −0.4510 (3) | 0.144 (2) | |
N1 | 0.9544 (3) | 0.0936 (2) | 0.1488 (3) | 0.059 (1) | |
N2 | 0.7619 (3) | −0.0055 (2) | 0.0733 (3) | 0.0520 (9) | |
N3 | 0.7592 (3) | 0.0177 (2) | −0.1264 (2) | 0.0489 (9) | |
N4 | 0.7161 (3) | 0.1857 (2) | 0.0383 (2) | 0.0501 (9) | |
C1 | 1.0384 (4) | 0.1551 (4) | 0.1794 (4) | 0.072 (1) | |
C2 | 1.0948 (5) | 0.1671 (5) | 0.2849 (5) | 0.094 (2) | |
C3 | 1.0629 (6) | 0.1157 (5) | 0.3577 (5) | 0.101 (2) | |
C4 | 0.9784 (5) | 0.0536 (4) | 0.3260 (4) | 0.089 (2) | |
C5 | 0.9246 (4) | 0.0431 (3) | 0.2195 (4) | 0.064 (1) | |
C6 | 0.8343 (4) | −0.0264 (4) | 0.1798 (3) | 0.067 (1) | |
C7 | 0.7348 (4) | −0.0840 (3) | 0.0052 (4) | 0.061 (1) | |
C8 | 0.7071 (4) | −0.0564 (3) | −0.1083 (3) | 0.052 (1) | |
C9 | 0.6371 (4) | −0.1048 (3) | −0.1891 (4) | 0.063 (1) | |
C10 | 0.6231 (4) | −0.0767 (3) | −0.2909 (4) | 0.068 (1) | |
C11 | 0.6767 (4) | −0.0006 (3) | −0.3098 (3) | 0.068 (1) | |
C12 | 0.7434 (4) | 0.0444 (3) | −0.2266 (3) | 0.059 (1) | |
C13 | 0.6497 (4) | 0.0382 (3) | 0.0753 (4) | 0.062 (1) | |
C14 | 0.6688 (4) | 0.1327 (3) | 0.1108 (3) | 0.059 (1) | |
C15 | 0.6223 (4) | 0.2086 (3) | −0.0571 (3) | 0.058 (1) | |
C16 | 0.6654 (4) | 0.2684 (3) | −0.1280 (3) | 0.066 (1) | |
C17 | 0.7163 (5) | 0.3519 (3) | −0.0728 (4) | 0.079 (2) | |
C18 | 0.8090 (5) | 0.3298 (3) | 0.0263 (4) | 0.073 (2) | |
C19 | 0.7635 (4) | 0.2679 (3) | 0.0949 (3) | 0.062 (1) | |
H1 | 1.0595 | 0.1911 | 0.1274 | 0.0861* | |
H2 | 1.1549 | 0.2106 | 0.3063 | 0.1125* | |
H3 | 1.1001 | 0.1233 | 0.4311 | 0.1212* | |
H4 | 0.9560 | 0.0173 | 0.3769 | 0.1062* | |
H5 | 0.7847 | −0.0308 | 0.2266 | 0.0807* | |
H6 | 0.8729 | −0.0815 | 0.1778 | 0.0807* | |
H7 | 0.8010 | −0.1226 | 0.0204 | 0.0738* | |
H8 | 0.6687 | −0.1138 | 0.0182 | 0.0738* | |
H9 | 0.5990 | −0.1570 | −0.1746 | 0.0759* | |
H10 | 0.5762 | −0.1100 | −0.3484 | 0.0813* | |
H11 | 0.6671 | 0.0203 | −0.3802 | 0.0820* | |
H12 | 0.7809 | 0.0974 | −0.2398 | 0.0714* | |
H13 | 0.5978 | 0.0367 | 0.0059 | 0.0742* | |
H14 | 0.6151 | 0.0070 | 0.1228 | 0.0742* | |
H15 | 0.7228 | 0.1342 | 0.1792 | 0.0709* | |
H16 | 0.5954 | 0.1572 | 0.1145 | 0.0709* | |
H17 | 0.5937 | 0.1558 | −0.0946 | 0.0701* | |
H18 | 0.5598 | 0.2369 | −0.0359 | 0.0701* | |
H19 | 0.7248 | 0.2388 | −0.1524 | 0.0794* | |
H20 | 0.6014 | 0.2832 | −0.1869 | 0.0794* | |
H21 | 0.7505 | 0.3858 | −0.1185 | 0.0945* | |
H22 | 0.6554 | 0.3853 | −0.0551 | 0.0945* | |
H23 | 0.8741 | 0.3030 | 0.0076 | 0.0877* | |
H24 | 0.8344 | 0.3828 | 0.0647 | 0.0877* | |
H25 | 0.7022 | 0.2965 | 0.1176 | 0.0746* | |
H26 | 0.8260 | 0.2531 | 0.1549 | 0.0746* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0438 (3) | 0.0582 (3) | 0.0480 (3) | −0.0068 (2) | 0.0156 (2) | −0.0054 (2) |
Cl1 | 0.0632 (7) | 0.0835 (8) | 0.0832 (8) | −0.0214 (6) | 0.0391 (6) | −0.0119 (6) |
P1 | 0.0777 (8) | 0.0535 (7) | 0.0613 (7) | −0.0110 (6) | 0.0113 (6) | −0.0022 (5) |
F1 | 0.118 (3) | 0.113 (3) | 0.146 (4) | −0.052 (2) | −0.024 (3) | 0.031 (3) |
F2 | 0.146 (3) | 0.114 (3) | 0.161 (4) | −0.017 (3) | −0.027 (3) | 0.072 (3) |
F3 | 0.180 (4) | 0.106 (3) | 0.206 (5) | −0.001 (3) | 0.125 (4) | −0.036 (3) |
F4 | 0.117 (3) | 0.115 (3) | 0.090 (2) | 0.018 (2) | 0.028 (2) | 0.035 (2) |
F5 | 0.093 (2) | 0.123 (3) | 0.120 (3) | −0.043 (2) | 0.029 (2) | −0.023 (2) |
F6 | 0.253 (6) | 0.108 (3) | 0.090 (3) | −0.012 (3) | 0.080 (3) | −0.025 (2) |
N1 | 0.045 (2) | 0.071 (2) | 0.056 (2) | 0.004 (2) | 0.007 (2) | −0.008 (2) |
N2 | 0.047 (2) | 0.055 (2) | 0.055 (2) | 0.003 (2) | 0.015 (1) | 0.007 (2) |
N3 | 0.051 (2) | 0.047 (2) | 0.049 (2) | −0.006 (2) | 0.016 (1) | −0.005 (1) |
N4 | 0.049 (2) | 0.056 (2) | 0.047 (2) | 0.006 (2) | 0.015 (1) | 0.000 (1) |
C1 | 0.048 (2) | 0.082 (3) | 0.081 (3) | 0.004 (2) | 0.009 (2) | −0.024 (3) |
C2 | 0.056 (3) | 0.112 (5) | 0.098 (4) | 0.010 (3) | −0.008 (3) | −0.038 (4) |
C3 | 0.075 (4) | 0.140 (6) | 0.070 (4) | 0.019 (4) | −0.011 (3) | −0.026 (4) |
C4 | 0.073 (3) | 0.122 (5) | 0.062 (3) | 0.025 (3) | 0.001 (3) | −0.003 (3) |
C5 | 0.053 (2) | 0.080 (3) | 0.058 (3) | 0.022 (2) | 0.010 (2) | −0.001 (2) |
C6 | 0.069 (3) | 0.081 (3) | 0.052 (2) | 0.011 (2) | 0.016 (2) | 0.011 (2) |
C7 | 0.059 (2) | 0.051 (2) | 0.073 (3) | −0.002 (2) | 0.015 (2) | 0.011 (2) |
C8 | 0.048 (2) | 0.046 (2) | 0.063 (3) | 0.002 (2) | 0.015 (2) | 0.000 (2) |
C9 | 0.052 (2) | 0.053 (2) | 0.082 (3) | −0.007 (2) | 0.013 (2) | −0.009 (2) |
C10 | 0.063 (3) | 0.073 (3) | 0.062 (3) | −0.004 (2) | 0.008 (2) | −0.016 (2) |
C11 | 0.078 (3) | 0.069 (3) | 0.055 (3) | 0.000 (3) | 0.013 (2) | −0.009 (2) |
C12 | 0.073 (3) | 0.055 (2) | 0.053 (2) | −0.001 (2) | 0.021 (2) | 0.000 (2) |
C13 | 0.050 (2) | 0.072 (3) | 0.069 (3) | 0.000 (2) | 0.026 (2) | 0.010 (2) |
C14 | 0.052 (2) | 0.076 (3) | 0.055 (2) | 0.010 (2) | 0.024 (2) | 0.002 (2) |
C15 | 0.051 (2) | 0.065 (3) | 0.055 (2) | 0.007 (2) | 0.007 (2) | −0.008 (2) |
C16 | 0.080 (3) | 0.063 (3) | 0.052 (2) | 0.009 (2) | 0.011 (2) | 0.002 (2) |
C17 | 0.092 (4) | 0.063 (3) | 0.080 (3) | 0.003 (3) | 0.022 (3) | 0.004 (3) |
C18 | 0.079 (3) | 0.060 (3) | 0.083 (3) | −0.009 (2) | 0.025 (3) | −0.023 (2) |
C19 | 0.063 (3) | 0.066 (3) | 0.055 (2) | 0.009 (2) | 0.012 (2) | −0.015 (2) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.243 (1) | C6—H6 | 0.960 |
Cu1—N1 | 2.006 (3) | C7—C8 | 1.506 (6) |
Cu1—N2 | 2.056 (3) | C7—H7 | 0.960 |
Cu1—N3 | 1.998 (3) | C7—H8 | 0.960 |
Cu1—N4 | 2.428 (3) | C8—C9 | 1.381 (6) |
P1—F1 | 1.579 (4) | C9—C10 | 1.377 (7) |
P1—F2 | 1.561 (4) | C9—H9 | 0.960 |
P1—F3 | 1.560 (4) | C10—C11 | 1.378 (7) |
P1—F4 | 1.578 (4) | C10—H10 | 0.960 |
P1—F5 | 1.565 (3) | C11—C12 | 1.358 (6) |
P1—F6 | 1.570 (4) | C11—H11 | 0.960 |
N1—C1 | 1.352 (6) | C12—H12 | 0.960 |
N1—C5 | 1.327 (6) | C13—C14 | 1.514 (7) |
N2—C6 | 1.477 (5) | C13—H13 | 0.960 |
N2—C7 | 1.480 (6) | C13—H14 | 0.960 |
N2—C13 | 1.495 (5) | C14—H15 | 0.960 |
N3—C8 | 1.340 (5) | C14—H16 | 0.960 |
N3—C12 | 1.349 (5) | C15—C16 | 1.490 (7) |
N4—C14 | 1.471 (5) | C15—H17 | 0.960 |
N4—C15 | 1.487 (5) | C15—H18 | 0.960 |
N4—C19 | 1.492 (6) | C16—C17 | 1.513 (7) |
C1—C2 | 1.390 (7) | C16—H19 | 0.960 |
C1—H1 | 0.960 | C16—H20 | 0.960 |
C2—C3 | 1.367 (10) | C17—C18 | 1.509 (7) |
C2—H2 | 0.960 | C17—H21 | 0.960 |
C3—C4 | 1.362 (9) | C17—H22 | 0.960 |
C3—H3 | 0.960 | C18—C19 | 1.502 (7) |
C4—C5 | 1.391 (7) | C18—H23 | 0.960 |
C4—H4 | 0.960 | C18—H24 | 0.960 |
C5—C6 | 1.501 (7) | C19—H25 | 0.960 |
C6—H5 | 0.960 | C19—H26 | 0.960 |
| | | |
Cl1···C6i | 3.551 (5) | F4···C10 | 3.348 (6) |
Cl1···C7i | 3.579 (5) | F4···C13iii | 3.411 (6) |
F1···C3ii | 3.331 (7) | F4···C11 | 3.434 (6) |
F1···C6iii | 3.402 (7) | F4···C6iii | 3.547 (6) |
F1···C17iv | 3.504 (7) | F5···C16 | 3.391 (6) |
F2···C7v | 3.330 (6) | F5···C9v | 3.452 (6) |
F2···C3ii | 3.459 (7) | F6···C11vi | 3.277 (6) |
F2···C9v | 3.541 (7) | F6···C10vi | 3.319 (6) |
F3···C9v | 3.291 (6) | F6···C11 | 3.423 (8) |
F3···C6iii | 3.508 (7) | C2···C10i | 3.600 (7) |
| | | |
Cl1—Cu1—N1 | 97.4 (1) | N2—C7—C8 | 109.4 (3) |
Cl1—Cu1—N2 | 171.0 (1) | N2—C7—H7 | 109.5 |
Cl1—Cu1—N3 | 95.2 (1) | N2—C7—H8 | 109.5 |
Cl1—Cu1—N4 | 106.1 (1) | C8—C7—H7 | 109.5 |
N1—Cu1—N2 | 83.3 (1) | C8—C7—H8 | 109.5 |
N1—Cu1—N3 | 158.4 (1) | H7—C7—H8 | 109.5 |
N1—Cu1—N4 | 90.0 (1) | N3—C8—C7 | 114.9 (4) |
N2—Cu1—N3 | 81.5 (1) | N3—C8—C9 | 121.7 (4) |
N2—Cu1—N4 | 82.9 (1) | C7—C8—C9 | 123.3 (4) |
N3—Cu1—N4 | 103.3 (1) | C8—C9—C10 | 118.8 (4) |
F1—P1—F2 | 91.9 (2) | C8—C9—H9 | 120.6 |
F1—P1—F3 | 89.6 (3) | C10—C9—H9 | 120.6 |
F1—P1—F4 | 87.2 (2) | C9—C10—C11 | 119.6 (4) |
F1—P1—F5 | 178.6 (3) | C9—C10—H10 | 120.2 |
F1—P1—F6 | 92.4 (3) | C11—C10—H10 | 120.2 |
F2—P1—F3 | 92.1 (3) | C10—C11—C12 | 118.6 (4) |
F2—P1—F4 | 179.0 (2) | C10—C11—H11 | 120.7 |
F2—P1—F5 | 88.1 (2) | C12—C11—H11 | 120.7 |
F2—P1—F6 | 91.8 (3) | N3—C12—C11 | 122.8 (4) |
F3—P1—F4 | 88.2 (3) | N3—C12—H12 | 118.6 |
F3—P1—F5 | 88.9 (2) | C11—C12—H12 | 118.6 |
F3—P1—F6 | 175.5 (3) | N2—C13—C14 | 111.7 (3) |
F4—P1—F5 | 92.8 (2) | N2—C13—H13 | 108.9 |
F4—P1—F6 | 87.9 (2) | N2—C13—H14 | 108.9 |
F5—P1—F6 | 89.0 (3) | C14—C13—H13 | 108.9 |
Cu1—N1—C1 | 125.1 (3) | C14—C13—H14 | 108.9 |
Cu1—N1—C5 | 114.2 (3) | H13—C13—H14 | 109.5 |
C1—N1—C5 | 120.3 (4) | N4—C14—C13 | 111.9 (3) |
Cu1—N2—C6 | 109.0 (3) | N4—C14—H15 | 108.9 |
Cu1—N2—C7 | 106.7 (2) | N4—C14—H16 | 108.9 |
Cu1—N2—C13 | 107.5 (2) | C13—C14—H15 | 108.9 |
C6—N2—C7 | 112.5 (3) | C13—C14—H16 | 108.9 |
C6—N2—C13 | 112.2 (3) | H15—C14—H16 | 109.5 |
C7—N2—C13 | 108.6 (3) | N4—C15—C16 | 111.8 (4) |
Cu1—N3—C8 | 115.1 (3) | N4—C15—H17 | 108.9 |
Cu1—N3—C12 | 126.5 (3) | N4—C15—H18 | 108.9 |
C8—N3—C12 | 118.5 (4) | C16—C15—H17 | 108.9 |
Cu1—N4—C14 | 98.4 (2) | C16—C15—H18 | 108.9 |
Cu1—N4—C15 | 112.4 (2) | H17—C15—H18 | 109.5 |
Cu1—N4—C19 | 118.6 (2) | C15—C16—C17 | 111.9 (4) |
C14—N4—C15 | 110.5 (3) | C15—C16—H19 | 108.9 |
C14—N4—C19 | 107.2 (3) | C15—C16—H20 | 108.9 |
C15—N4—C19 | 109.0 (3) | C17—C16—H19 | 108.9 |
N1—C1—C2 | 120.9 (6) | C17—C16—H20 | 108.9 |
N1—C1—H1 | 119.5 | H19—C16—H20 | 109.5 |
C2—C1—H1 | 119.5 | C16—C17—C18 | 109.7 (4) |
C1—C2—C3 | 118.6 (6) | C16—C17—H21 | 109.4 |
C1—C2—H2 | 120.7 | C16—C17—H22 | 109.4 |
C3—C2—H2 | 120.7 | C18—C17—H21 | 109.4 |
C2—C3—C4 | 119.9 (5) | C18—C17—H22 | 109.4 |
C2—C3—H3 | 120.0 | H21—C17—H22 | 109.5 |
C4—C3—H3 | 120.0 | C17—C18—C19 | 111.5 (4) |
C3—C4—C5 | 119.8 (6) | C17—C18—H23 | 109.0 |
C3—C4—H4 | 120.1 | C17—C18—H24 | 109.0 |
C5—C4—H4 | 120.1 | C19—C18—H23 | 109.0 |
N1—C5—C4 | 120.4 (5) | C19—C18—H24 | 109.0 |
N1—C5—C6 | 117.4 (4) | H23—C18—H24 | 109.5 |
C4—C5—C6 | 122.1 (5) | N4—C19—C18 | 112.1 (3) |
N2—C6—C5 | 111.4 (4) | N4—C19—H25 | 108.8 |
N2—C6—H5 | 109.0 | N4—C19—H26 | 108.8 |
N2—C6—H6 | 109.0 | C18—C19—H25 | 108.8 |
C5—C6—H5 | 109.0 | C18—C19—H26 | 108.8 |
C5—C6—H6 | 109.0 | H25—C19—H26 | 109.5 |
H5—C6—H6 | 109.5 | | |
Symmetry codes: (i) −x+2, −y, −z; (ii) x−1, y, z−1; (iii) −x+1, −y, −z; (iv) −x+1, y−1/2, −z−1/2; (v) −x+1, y+1/2, −z−1/2; (vi) −x+1, −y, −z−1. |