Four copper(II) complexes with potentially tetradentate tripodal ligands

Kani, Y.; Ohba, S.; Ito, S.; Nishida, Y.

doi:10.1107/S010827010000603X

Four copper(II) complexes with potentially tetradentate tripodal ligands

The four title Cu^II 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000603X/qa0275sup1.cif Contains datablocks global, I, II, III, IV
	Structure factor file (CIF format) https://doi.org/10.1107/S010827010000603X/qa0275Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S010827010000603X/qa0275IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S010827010000603X/qa0275IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S010827010000603X/qa0275IVsup5.hkl Contains datablock IV

CCDC references: 146078; 146079; 146080; 146081

Computing details top

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.

(I) top

Crystal data top

[CuCl(C₁₇H₁₇N₃O)]ClO₄	Z = 4
M_r = 477.79	D_x = 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	R_int = 0.011
θ–2θ scans	θ_max = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = 0→18
T_min = 0.477, T_max = 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(F_o²) + (0.1(F_o² + 2F_c²)/3)²]
wR(F²) = 0.148	(Δ/σ)_max = 0.003
S = 0.99	Δρ_max = 0.42 e Å⁻³
8895 reflections	Δρ_min = −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	U_iso*/U_eq
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···O6^vi	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···C9^viii	3.403 (7)
Cl1···N1ⁱ	3.356 (3)	O7···C29	3.516 (7)
Cl1···C6ⁱ	3.480 (4)	O8···C17^ix	3.276 (7)
Cl1···C7ⁱ	3.518 (4)	O8···C16^ix	3.344 (7)
Cl1···N2ⁱ	3.536 (3)	O8···C32^x	3.384 (8)
Cl2···C24ⁱⁱ	3.398 (4)	O8···C2ⁱ	3.559 (7)
Cl2···N6ⁱⁱ	3.424 (3)	O9···C21^x	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···C20^x	3.188 (6)
O3···C6	3.463 (6)	O10···C7^viii	3.338 (6)
O3···C23^iv	3.490 (8)	O10···C21^x	3.430 (6)
O3···C13	3.513 (6)	N3···C1ⁱ	3.571 (5)
O3···C20^v	3.525 (8)	C1···C12ⁱ	3.558 (6)
O4···C3^vi	3.210 (6)	C13···C14ⁱⁱⁱ	3.439 (5)
O4···C4^vi	3.357 (6)	C13···C17ⁱⁱⁱ	3.569 (6)
O4···C28^vii	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.

(II) top

Crystal data top

[Cu(C₁₄H₁₇N₃O)Cl][CuCl₄]_0.5	D_x = 1.720 Mg m⁻³
M_r = 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	R_int = 0.041
θ–2θ scans	θ_max = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = 0→30
T_min = 0.331, T_max = 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(F_o²) + (0.1(F_o² + 2F_c²)/3)²]
wR(F²) = 0.131	(Δ/σ)_max = 0.026
S = 1.00	Δρ_max = 0.51 e Å⁻³
3943 reflections	Δρ_min = −0.86 e Å⁻³
207 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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···C10^iv	3.588 (5)
Cl3···C4	3.546 (4)	C2···C12ⁱⁱ	3.487 (5)
Cl3···C14ⁱⁱⁱ	3.571 (4)	C3···C12ⁱⁱ	3.544 (6)
O1···C10^iv	3.312 (4)	C9···H1^v	3.51 (4)
O1···C9^iv	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.

(III) top

Crystal data top

[Cu(C₁₈H₂₄N₄O)Cl]ClO₄	D_x = 1.599 Mg m⁻³
M_r = 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	R_int = 0.015
θ–2θ scans	θ_max = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = 0→12
T_min = 0.638, T_max = 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(F_o²) + (0.1(F_o² + 2F_c²)/3)²]
wR(F²) = 0.197	(Δ/σ)_max = 0.011
S = 1.32	Δρ_max = 0.59 e Å⁻³
4878 reflections	Δρ_min = −0.48 e Å⁻³
271 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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···C10^iv	3.340 (8)
O1···C6ⁱⁱ	3.197 (6)	O3···C4^v	3.42 (1)
O1···C7ⁱⁱ	3.423 (6)	O3···C17^vi	3.474 (10)
O2···C15	3.244 (8)	O3···C6^v	3.511 (9)
O2···C4ⁱⁱⁱ	3.361 (10)	O4···C17^vii	3.212 (8)
O2···C10	3.37 (1)	O4···C1^vii	3.497 (9)
O2···C11	3.395 (9)	O4···C10	3.538 (9)
O2···C3ⁱⁱⁱ	3.42 (1)	O5···C14^v	3.167 (8)
O2···C9	3.44 (1)	O5···C13^v	3.407 (8)
O2···C12	3.477 (9)	O5···C13	3.457 (9)
O2···C8	3.505 (9)	O5···C2^vii	3.50 (1)
O2···N3	3.553 (8)	O5···C9	3.56 (1)
O3···C11^iv	3.338 (9)	C6···C17^viii	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.

(IV) top

Crystal data top

[Cu(C₁₉H₂₆N₄)Cl]PF₆	D_x = 1.599 Mg m⁻³
M_r = 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	R_int = 0.026
θ–2θ scans	θ_max = 25.0°
Absorption correction: integration (Coppens et al., 1965)	h = 0→14
T_min = 0.654, T_max = 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(F_o²) + (0.1(F_o² + 2F_c²)/3)²]
wR(F²) = 0.147	(Δ/σ)_max = 0.002
S = 0.99	Δρ_max = 0.33 e Å⁻³
4048 reflections	Δρ_min = −0.27 e Å⁻³
289 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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···C17^iv	3.504 (7)	F5···C16	3.391 (6)
F2···C7^v	3.330 (6)	F5···C9^v	3.452 (6)
F2···C3ⁱⁱ	3.459 (7)	F6···C11^vi	3.277 (6)
F2···C9^v	3.541 (7)	F6···C10^vi	3.319 (6)
F3···C9^v	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.

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