Change in electronic structure in a six-coordinate copper(II) complex accompanied by an anion order/disorder transition

Kilner, C.A.; Halcrow, M.A.

doi:10.1107/S0108768110003678

Change in electronic structure in a six-coordinate copper(II) complex accompanied by an anion order/disorder transition

A variable-temperature crystallographic study of [Cu(L^OH)₂][ClO₄]₂·2(CH₃)₂CO [L^OH = 2,6-bis(hydroxyiminomethyl)pyridine] between 30 and 300 K is presented. The complex exhibits an unusual electronic structure at room temperature with a { $d_{z^2}$ }¹ ground state, corresponding to an axially compressed ligand coordination geometry about the copper ion. This reflects a suppression of the pseudo-Jahn–Teller distortion that is normally shown by copper(II) compounds with this ligand geometry [Halcrow et al. (2004). New J. Chem. 28, 228–233]. On cooling the compound undergoes an abrupt structural change at 157 ± 3 K, that does not involve a change in the space group (P $\bar 1$ ), but causes significant changes to c and the unit-cell angles. This reflects a conformational rearrangement of the complex dication, towards a more typical pseudo-Jahn–Teller elongated coordination geometry. This occurs concurrently with a crystallographic ordering of one of the two perchlorate anions, and a significant displacement of the two lattice acetone molecules. The transformation involves displacements of up to 0.5 Å in the non-H atoms of the structure at 30 K, compared with their positions at 300 K. The change in coordination geometry of the complex around 157 K is reflected in a small reduction in its magnetic moment near that temperature.

Keywords: Jahn–Teller distortion; variable-temperature crystallography; order/disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110003678/zb5011sup1.cif Contains datablocks mh68300, mh68250, mh68200, mh68150, mh68100, mh6830, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh68300sup2.hkl Contains datablock mh68300
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh68250sup3.hkl Contains datablock mh68250
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh68200sup4.hkl Contains datablock mh68200
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh68150sup5.hkl Contains datablock mh68150
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh68100sup6.hkl Contains datablock mh68100
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110003678/zb5011mh6830sup7.hkl Contains datablock mh6830

CCDC references: 775201; 775202; 775203; 775204; 775205; 775206

Computing details top

Data collection: COLLECT (Nonius, 1999) for mh68300, mh68250, mh68200, mh68150, mh68100; APEX 2 software, Bruker Nonius 2004 for mh6830. Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for mh68300, mh68250, mh68200, mh68150, mh68100; APEX 2 software, Bruker Nonius 2004 for mh6830. Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for mh68300, mh68250, mh68200, mh68150, mh68100; SAINT, Bruker Nonius 2004 for mh6830. For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: local program.

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh68300) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.576 Mg m⁻³
a = 7.1699 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.2151 (3) Å	Cell parameters from 24994 reflections
c = 17.3664 (5) Å	θ = 3.0–27.4°
α = 107.6727 (15)°	µ = 0.98 mm⁻¹
β = 96.0833 (14)°	T = 300 K
γ = 103.7596 (12)°	Rectangular prism, green
V = 1494.34 (7) Å³	0.26 × 0.23 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer	6655 independent reflections
Radiation source: fine-focus sealed tube	5396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.128
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
/w and /f scans	h = −9→9
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38	k = −17→16
T_min = 0.784, T_max = 0.858	l = −22→22
24994 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.199	w = 1/[σ²(F_o²) + (0.1193P)² + 0.4196P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6655 reflections	Δρ_max = 0.64 e Å⁻³
448 parameters	Δρ_min = −0.82 e Å⁻³
70 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (8)

Special details top

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Both ClO₄^- anions are disordered. Cl26A—O30A, occupancy 0.40 Cl26B—O30B, occupancy 0.40 Cl26C—O30C, occupancy 0.20 and Cl31A—O35A, occupancy 0.40 Cl31B—O35B, occupancy 0.30 Cl31C—O35C, occupancy 0.15 Cl31D—O35D, occupancy 0.15 A l l disordered Cl—O bonds were restrained to 1.44 (2)%A, and non-bonded O···O distances within a given disorder orientation were restrained to 2.35 (2) Å. All wholly occupied non-H atoms were refined anisotropically, while all H atoms were placed in calculated positions and refined using a riding model.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.35207 (5)	0.57361 (3)	0.26304 (2)	0.0545 (2)
N2	0.4821 (4)	0.7302 (2)	0.30278 (17)	0.0577 (6)
C3	0.6551 (5)	0.7686 (3)	0.2821 (2)	0.0641 (8)
C4	0.7552 (6)	0.8798 (3)	0.3113 (3)	0.0793 (11)
H4	0.8751	0.9055	0.2976	0.095*
C5	0.6706 (7)	0.9529 (3)	0.3622 (3)	0.0836 (12)
H5	0.7345	1.0284	0.3830	0.100*
C6	0.4949 (7)	0.9136 (3)	0.3813 (3)	0.0764 (10)
H6	0.4371	0.9622	0.4142	0.092*
C7	0.4030 (6)	0.8013 (3)	0.3515 (2)	0.0620 (8)
C8	0.7238 (6)	0.6820 (3)	0.2285 (2)	0.0697 (9)
H8	0.8415	0.6989	0.2107	0.084*
N9	0.6164 (5)	0.5831 (3)	0.2072 (2)	0.0677 (7)
O10	0.6912 (5)	0.5075 (3)	0.1564 (2)	0.0977 (10)
H10	0.6132	0.4456	0.1421	0.117*
C11	0.2159 (6)	0.7487 (3)	0.3695 (2)	0.0677 (9)
H11	0.1472	0.7901	0.4023	0.081*
N12	0.1526 (4)	0.6436 (2)	0.33795 (17)	0.0618 (7)
O13	−0.0216 (5)	0.6004 (3)	0.3580 (2)	0.0863 (8)
H13	−0.0528	0.5326	0.3384	0.104*
N14	0.2229 (4)	0.4143 (2)	0.22133 (16)	0.0540 (6)
C15	0.0998 (5)	0.3674 (3)	0.1481 (2)	0.0602 (7)
C16	0.0090 (6)	0.2543 (3)	0.1160 (2)	0.0747 (10)
H16	−0.0784	0.2231	0.0659	0.090*
C17	0.0517 (7)	0.1888 (3)	0.1606 (3)	0.0764 (10)
H17	−0.0040	0.1125	0.1396	0.092*
C18	0.1769 (6)	0.2370 (3)	0.2359 (3)	0.0714 (9)
H18	0.2054	0.1939	0.2666	0.086*
C19	0.2590 (5)	0.3502 (3)	0.2651 (2)	0.0583 (7)
C20	0.0674 (6)	0.4423 (3)	0.1053 (2)	0.0672 (9)
H20	−0.0158	0.4165	0.0543	0.081*
N21	0.1570 (5)	0.5444 (2)	0.14024 (17)	0.0623 (7)
O22	0.1170 (6)	0.6095 (2)	0.09487 (19)	0.0892 (9)
H22	0.1607	0.6751	0.1234	0.107*
C23	0.3934 (5)	0.4102 (3)	0.3449 (2)	0.0604 (8)
H23	0.4184	0.3741	0.3815	0.073*
N24	0.4733 (4)	0.5123 (2)	0.36210 (17)	0.0613 (7)
O25	0.5974 (5)	0.5605 (2)	0.43710 (17)	0.0803 (8)
H25	0.6532	0.6251	0.4433	0.096*
Cl26A	0.7827 (13)	0.8511 (6)	0.5468 (4)	0.061 (2)*	0.40
O27A	0.7559 (14)	0.7763 (8)	0.4643 (5)	0.068 (2)*	0.40
O28A	0.5862 (14)	0.8207 (9)	0.5675 (7)	0.087 (3)*	0.40
O29A	0.9144 (15)	0.8477 (8)	0.6118 (5)	0.081 (2)*	0.40
O30A	0.8064 (16)	0.9631 (7)	0.5444 (7)	0.079 (3)*	0.40
Cl26B	0.7490 (8)	0.8451 (4)	0.5450 (3)	0.0672 (16)*	0.40
O27B	0.8199 (17)	0.7752 (8)	0.4736 (5)	0.075 (3)*	0.40
O28B	0.5536 (11)	0.8251 (7)	0.5362 (6)	0.083 (2)*	0.40
O29B	0.8353 (17)	0.8123 (10)	0.6102 (6)	0.111 (3)*	0.40
O30B	0.8597 (15)	0.9570 (7)	0.5493 (7)	0.074 (3)*	0.40
Cl26C	0.8027 (17)	0.8441 (8)	0.5471 (6)	0.058 (3)*	0.20
O27C	0.805 (4)	0.7916 (15)	0.4622 (9)	0.071 (6)*	0.20
O28C	0.618 (2)	0.7950 (17)	0.5671 (13)	0.102 (7)*	0.20
O29C	0.956 (2)	0.8259 (16)	0.5962 (11)	0.092 (6)*	0.20
O30C	0.829 (3)	0.9620 (9)	0.5696 (10)	0.058 (4)*	0.20
Cl31A	0.1772 (7)	0.8984 (3)	0.1585 (4)	0.0664 (14)*	0.40
O32A	0.1665 (14)	0.8199 (7)	0.1995 (5)	0.076 (2)*	0.40
O33A	0.3540 (16)	0.9928 (9)	0.1834 (8)	0.118 (3)*	0.40
O34A	0.0118 (18)	0.9299 (12)	0.1590 (9)	0.151 (5)*	0.40
O35A	0.2063 (19)	0.8412 (9)	0.0707 (5)	0.109 (3)*	0.40
Cl31B	0.2478 (8)	0.8958 (4)	0.1518 (5)	0.0662 (17)*	0.30
O32B	0.228 (2)	0.8160 (9)	0.1954 (8)	0.081 (4)*	0.30
O33B	0.4337 (17)	0.9564 (12)	0.1715 (8)	0.111 (4)*	0.30
O34B	0.115 (3)	0.9653 (15)	0.1972 (12)	0.140 (6)*	0.30
O35B	0.123 (2)	0.8466 (12)	0.0735 (7)	0.098 (4)*	0.30
Cl31C	0.204 (2)	0.8950 (7)	0.1478 (6)	0.043 (2)*	0.15
O32C	0.303 (3)	0.8280 (13)	0.1813 (12)	0.060 (4)*	0.15
O33C	0.206 (5)	0.9917 (16)	0.2226 (12)	0.097 (7)*	0.15
O34C	0.003 (3)	0.835 (2)	0.114 (2)	0.151 (12)*	0.15
O35C	0.302 (5)	0.937 (3)	0.0944 (18)	0.199 (19)*	0.15
Cl31D	0.2208 (17)	0.9011 (5)	0.1690 (5)	0.0445 (18)*	0.15
O32D	0.051 (4)	0.856 (3)	0.1969 (18)	0.158 (13)*	0.15
O33D	0.319 (4)	1.0105 (12)	0.2193 (13)	0.091 (6)*	0.15
O34D	0.151 (4)	0.904 (2)	0.0852 (10)	0.105 (8)*	0.15
O35D	0.349 (3)	0.8305 (16)	0.1566 (14)	0.090 (7)*	0.15
O36	−0.1577 (5)	0.3813 (3)	0.2925 (2)	0.0942 (9)
C37	−0.2014 (6)	0.3188 (3)	0.3311 (3)	0.0784 (11)
C38	−0.3180 (8)	0.2022 (4)	0.2862 (3)	0.0951 (14)
H38A	−0.4188	0.1811	0.3153	0.114*
H38B	−0.2341	0.1548	0.2826	0.114*
H38C	−0.3765	0.1951	0.2318	0.114*
C39	−0.1472 (10)	0.3543 (5)	0.4221 (4)	0.1136 (18)
H39A	−0.0496	0.3210	0.4366	0.136*
H39B	−0.2609	0.3312	0.4441	0.136*
H39C	−0.0959	0.4335	0.4445	0.136*
O40	0.4956 (6)	0.2931 (3)	0.1033 (2)	0.0999 (10)
C41	0.4290 (8)	0.2390 (4)	0.0333 (3)	0.0880 (12)
C42	0.4016 (12)	0.2926 (6)	−0.0292 (4)	0.129 (2)
H42A	0.4841	0.2752	−0.0685	0.155*
H42B	0.4357	0.3715	−0.0025	0.155*
H42C	0.2673	0.2658	−0.0571	0.155*
C43	0.3558 (11)	0.1145 (5)	0.0057 (4)	0.120 (2)
H43A	0.4036	0.0895	0.0482	0.144*
H43B	0.4019	0.0829	−0.0435	0.144*
H43C	0.2153	0.0918	−0.0053	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0591 (3)	0.0454 (3)	0.0548 (3)	0.01192 (18)	0.00737 (18)	0.01465 (17)
N2	0.0652 (16)	0.0468 (13)	0.0554 (14)	0.0119 (12)	0.0013 (12)	0.0160 (11)
C3	0.065 (2)	0.0574 (18)	0.0649 (19)	0.0043 (15)	0.0030 (15)	0.0267 (15)
C4	0.075 (2)	0.065 (2)	0.088 (3)	−0.0031 (18)	0.000 (2)	0.033 (2)
C5	0.100 (3)	0.0510 (19)	0.081 (3)	−0.001 (2)	−0.010 (2)	0.0234 (18)
C6	0.093 (3)	0.0479 (17)	0.076 (2)	0.0143 (18)	−0.003 (2)	0.0146 (16)
C7	0.073 (2)	0.0487 (16)	0.0577 (17)	0.0167 (15)	0.0002 (15)	0.0137 (13)
C8	0.0596 (19)	0.071 (2)	0.076 (2)	0.0065 (17)	0.0146 (17)	0.0304 (18)
N9	0.0678 (18)	0.0648 (17)	0.0689 (17)	0.0169 (14)	0.0139 (14)	0.0221 (14)
O10	0.092 (2)	0.0770 (19)	0.117 (3)	0.0224 (17)	0.044 (2)	0.0161 (18)
C11	0.078 (2)	0.0544 (18)	0.0647 (19)	0.0237 (17)	0.0118 (17)	0.0087 (15)
N12	0.0646 (17)	0.0541 (15)	0.0614 (15)	0.0150 (13)	0.0087 (13)	0.0149 (12)
O13	0.0807 (19)	0.0692 (16)	0.099 (2)	0.0129 (14)	0.0286 (16)	0.0175 (16)
N14	0.0579 (15)	0.0447 (12)	0.0551 (14)	0.0124 (11)	0.0084 (11)	0.0136 (10)
C15	0.0647 (19)	0.0500 (16)	0.0593 (17)	0.0131 (14)	0.0070 (14)	0.0132 (13)
C16	0.081 (2)	0.0542 (18)	0.069 (2)	0.0082 (17)	0.0003 (18)	0.0059 (16)
C17	0.094 (3)	0.0434 (16)	0.079 (2)	0.0095 (17)	0.011 (2)	0.0127 (16)
C18	0.081 (2)	0.0526 (17)	0.082 (2)	0.0168 (17)	0.0161 (19)	0.0264 (17)
C19	0.0613 (18)	0.0500 (15)	0.0636 (18)	0.0164 (14)	0.0130 (14)	0.0187 (14)
C20	0.077 (2)	0.0571 (18)	0.0529 (17)	0.0111 (16)	−0.0048 (15)	0.0101 (14)
N21	0.0699 (18)	0.0550 (15)	0.0587 (15)	0.0146 (13)	0.0056 (13)	0.0193 (12)
O22	0.123 (3)	0.0623 (16)	0.0759 (18)	0.0170 (17)	−0.0048 (16)	0.0302 (14)
C23	0.067 (2)	0.0559 (17)	0.0628 (18)	0.0185 (15)	0.0094 (15)	0.0268 (15)
N24	0.0664 (17)	0.0563 (15)	0.0600 (15)	0.0151 (13)	0.0095 (13)	0.0208 (12)
O25	0.088 (2)	0.0685 (16)	0.0681 (15)	0.0029 (14)	−0.0056 (13)	0.0221 (13)
O36	0.097 (2)	0.0668 (17)	0.112 (2)	0.0117 (15)	0.0317 (19)	0.0256 (17)
C37	0.068 (2)	0.065 (2)	0.099 (3)	0.0197 (18)	0.023 (2)	0.022 (2)
C38	0.093 (3)	0.070 (3)	0.107 (3)	0.002 (2)	0.017 (3)	0.025 (2)
C39	0.117 (5)	0.101 (4)	0.104 (4)	0.026 (3)	−0.003 (3)	0.020 (3)
O40	0.114 (3)	0.078 (2)	0.093 (2)	0.0202 (18)	0.0150 (19)	0.0174 (18)
C41	0.086 (3)	0.080 (3)	0.098 (3)	0.026 (2)	0.027 (3)	0.025 (3)
C42	0.145 (6)	0.128 (5)	0.114 (5)	0.030 (4)	0.023 (4)	0.050 (4)
C43	0.140 (5)	0.082 (3)	0.124 (5)	0.033 (3)	0.028 (4)	0.013 (3)

Geometric parameters (Å, º) top

Cu1—N2	1.926 (3)	Cl26A—O27A	1.435 (9)
Cu1—N14	1.954 (3)	Cl26A—O30A	1.463 (10)
Cu1—N12	2.210 (3)	Cl26A—O28A	1.483 (11)
Cu1—N9	2.213 (3)	Cl26B—O28B	1.346 (8)
Cu1—N24	2.288 (3)	Cl26B—O29B	1.459 (10)
Cu1—N21	2.294 (3)	Cl26B—O30B	1.478 (9)
N2—C7	1.339 (5)	Cl26B—O27B	1.521 (9)
N2—C3	1.353 (5)	Cl26C—O27C	1.430 (13)
C3—C4	1.379 (5)	Cl26C—O29C	1.432 (14)
C3—C8	1.461 (6)	Cl26C—O30C	1.445 (12)
C4—C5	1.398 (7)	Cl26C—O28C	1.457 (14)
C4—H4	0.9300	Cl31A—O34A	1.347 (11)
C5—C6	1.359 (7)	Cl31A—O32A	1.419 (8)
C5—H5	0.9300	Cl31A—O33A	1.468 (10)
C6—C7	1.379 (5)	Cl31A—O35A	1.545 (10)
C6—H6	0.9300	Cl31B—O33B	1.328 (11)
C7—C11	1.469 (5)	Cl31B—O35B	1.415 (11)
C8—N9	1.268 (5)	Cl31B—O32B	1.463 (11)
C8—H8	0.9300	Cl31B—O34B	1.585 (12)
N9—O10	1.372 (4)	Cl31C—O35C	1.390 (16)
O10—H10	0.8200	Cl31C—O34C	1.433 (17)
C11—N12	1.274 (5)	Cl31C—O32C	1.465 (14)
C11—H11	0.9300	Cl31C—O33C	1.518 (15)
N12—O13	1.371 (4)	Cl31D—O33D	1.402 (14)
O13—H13	0.8200	Cl31D—O32D	1.423 (16)
N14—C15	1.343 (4)	Cl31D—O35D	1.443 (15)
N14—C19	1.348 (4)	Cl31D—O34D	1.504 (14)
C15—C16	1.386 (5)	O36—C37	1.220 (5)
C15—C20	1.451 (5)	C37—C38	1.484 (6)
C16—C17	1.387 (6)	C37—C39	1.484 (7)
C16—H16	0.9300	C38—H38A	0.9600
C17—C18	1.377 (6)	C38—H38B	0.9600
C17—H17	0.9300	C38—H38C	0.9600
C18—C19	1.378 (5)	C39—H39A	0.9600
C18—H18	0.9300	C39—H39B	0.9600
C19—C23	1.471 (5)	C39—H39C	0.9600
C20—N21	1.269 (5)	O40—C41	1.185 (6)
C20—H20	0.9300	C41—C42	1.486 (8)
N21—O22	1.387 (4)	C41—C43	1.507 (7)
O22—H22	0.8200	C42—H42A	0.9600
C23—N24	1.261 (4)	C42—H42B	0.9600
C23—H23	0.9300	C42—H42C	0.9600
N24—O25	1.369 (4)	C43—H43A	0.9600
O25—H25	0.8200	C43—H43B	0.9600
Cl26A—O29A	1.412 (10)	C43—H43C	0.9600

N2—Cu1—N14	179.04 (11)	C23—N24—Cu1	110.6 (2)
N2—Cu1—N12	77.21 (12)	O25—N24—Cu1	135.7 (2)
N14—Cu1—N12	103.72 (11)	N24—O25—H25	109.5
N2—Cu1—N9	77.32 (12)	O29A—Cl26A—O27A	121.1 (8)
N14—Cu1—N9	101.75 (12)	O29A—Cl26A—O30A	113.0 (7)
N12—Cu1—N9	154.52 (12)	O27A—Cl26A—O30A	108.7 (7)
N2—Cu1—N24	104.07 (11)	O29A—Cl26A—O28A	105.5 (7)
N14—Cu1—N24	76.19 (11)	O27A—Cl26A—O28A	102.7 (7)
N12—Cu1—N24	92.75 (11)	O30A—Cl26A—O28A	103.8 (8)
N9—Cu1—N24	93.86 (11)	O28B—Cl26B—O29B	113.5 (7)
N2—Cu1—N21	103.98 (11)	O28B—Cl26B—O30B	116.0 (7)
N14—Cu1—N21	75.75 (11)	O29B—Cl26B—O30B	111.8 (7)
N12—Cu1—N21	93.78 (11)	O28B—Cl26B—O27B	115.2 (7)
N9—Cu1—N21	91.86 (12)	O29B—Cl26B—O27B	98.5 (7)
N24—Cu1—N21	151.95 (10)	O30B—Cl26B—O27B	99.7 (6)
C7—N2—C3	119.9 (3)	O27C—Cl26C—O29C	108.5 (12)
C7—N2—Cu1	120.3 (2)	O27C—Cl26C—O30C	113.4 (11)
C3—N2—Cu1	119.9 (2)	O29C—Cl26C—O30C	108.8 (11)
N2—C3—C4	121.5 (4)	O27C—Cl26C—O28C	110.3 (12)
N2—C3—C8	114.0 (3)	O29C—Cl26C—O28C	107.9 (11)
C4—C3—C8	124.5 (4)	O30C—Cl26C—O28C	107.8 (11)
C3—C4—C5	117.9 (4)	O34A—Cl31A—O32A	108.9 (7)
C3—C4—H4	121.1	O34A—Cl31A—O33A	112.6 (8)
C5—C4—H4	121.1	O32A—Cl31A—O33A	117.9 (7)
C6—C5—C4	120.1 (4)	O34A—Cl31A—O35A	112.8 (8)
C6—C5—H5	120.0	O32A—Cl31A—O35A	106.5 (6)
C4—C5—H5	120.0	O33A—Cl31A—O35A	97.6 (7)
C5—C6—C7	119.6 (4)	O33B—Cl31B—O35B	128.9 (9)
C5—C6—H6	120.2	O33B—Cl31B—O32B	107.6 (9)
C7—C6—H6	120.2	O35B—Cl31B—O32B	109.7 (8)
N2—C7—C6	121.1 (4)	O33B—Cl31B—O34B	110.6 (10)
N2—C7—C11	114.3 (3)	O35B—Cl31B—O34B	97.5 (9)
C6—C7—C11	124.6 (3)	O32B—Cl31B—O34B	97.9 (8)
N9—C8—C3	117.3 (3)	O35C—Cl31C—O34C	114.3 (15)
N9—C8—H8	121.4	O35C—Cl31C—O32C	113.3 (15)
C3—C8—H8	121.4	O34C—Cl31C—O32C	109.8 (13)
C8—N9—O10	113.4 (3)	O35C—Cl31C—O33C	108.0 (14)
C8—N9—Cu1	111.5 (3)	O34C—Cl31C—O33C	106.3 (14)
O10—N9—Cu1	135.1 (2)	O32C—Cl31C—O33C	104.4 (11)
N9—O10—H10	109.5	O33D—Cl31D—O32D	112.0 (14)
N12—C11—C7	116.6 (3)	O33D—Cl31D—O35D	112.7 (13)
N12—C11—H11	121.7	O32D—Cl31D—O35D	112.6 (13)
C7—C11—H11	121.7	O33D—Cl31D—O34D	106.9 (12)
C11—N12—O13	113.3 (3)	O32D—Cl31D—O34D	106.5 (13)
C11—N12—Cu1	111.7 (3)	O35D—Cl31D—O34D	105.6 (12)
O13—N12—Cu1	135.0 (2)	O36—C37—C38	119.3 (5)
N12—O13—H13	109.5	O36—C37—C39	123.1 (5)
C15—N14—C19	119.3 (3)	C38—C37—C39	117.6 (4)
C15—N14—Cu1	120.3 (2)	C37—C38—H38A	109.5
C19—N14—Cu1	120.4 (2)	C37—C38—H38B	109.5
N14—C15—C16	121.7 (3)	H38A—C38—H38B	109.5
N14—C15—C20	115.9 (3)	C37—C38—H38C	109.5
C16—C15—C20	122.4 (3)	H38A—C38—H38C	109.5
C15—C16—C17	118.4 (4)	H38B—C38—H38C	109.5
C15—C16—H16	120.8	C37—C39—H39A	109.5
C17—C16—H16	120.8	C37—C39—H39B	109.5
C18—C17—C16	119.9 (3)	H39A—C39—H39B	109.5
C18—C17—H17	120.0	C37—C39—H39C	109.5
C16—C17—H17	120.0	H39A—C39—H39C	109.5
C17—C18—C19	118.8 (3)	H39B—C39—H39C	109.5
C17—C18—H18	120.6	O40—C41—C42	120.8 (5)
C19—C18—H18	120.6	O40—C41—C43	121.4 (5)
N14—C19—C18	121.8 (3)	C42—C41—C43	117.7 (5)
N14—C19—C23	114.9 (3)	C41—C42—H42A	109.5
C18—C19—C23	123.3 (3)	C41—C42—H42B	109.5
N21—C20—C15	117.4 (3)	H42A—C42—H42B	109.5
N21—C20—H20	121.3	C41—C42—H42C	109.5
C15—C20—H20	121.3	H42A—C42—H42C	109.5
C20—N21—O22	113.3 (3)	H42B—C42—H42C	109.5
C20—N21—Cu1	110.7 (2)	C41—C43—H43A	109.5
O22—N21—Cu1	136.1 (2)	C41—C43—H43B	109.5
N21—O22—H22	109.5	H43A—C43—H43B	109.5
N24—C23—C19	117.8 (3)	C41—C43—H43C	109.5
N24—C23—H23	121.1	H43A—C43—H43C	109.5
C19—C23—H23	121.1	H43B—C43—H43C	109.5
C23—N24—O25	113.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.82	1.86	2.663 (5)	165
O13—H13···O36	0.82	1.84	2.655 (5)	172
O22—H22···O32A	0.82	1.96	2.735 (9)	159
O22—H22···O32B	0.82	1.81	2.628 (13)	171
O22—H22···O32C	0.82	1.92	2.736 (17)	170
O22—H22···O32D	0.82	2.69	3.38 (3)	143
O22—H22···O35A	0.82	2.59	3.141 (11)	126
O22—H22···O35B	0.82	2.72	3.256 (15)	125
O22—H22···O35D	0.82	2.04	2.80 (2)	154
O25—H25···O27A	0.82	1.86	2.678 (11)	173
O25—H25···O27B	0.82	1.94	2.745 (12)	169
O25—H25···O27C	0.82	2.12	2.94 (2)	178

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh68250) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.595 Mg m⁻³
a = 7.1247 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1767 (4) Å	Cell parameters from 27221 reflections
c = 17.2946 (6) Å	θ = 2.5–27.4°
α = 107.7323 (17)°	µ = 1.00 mm⁻¹
β = 96.0184 (16)°	T = 250 K
γ = 103.5657 (13)°	Rectangular prism, green
V = 1475.84 (8) Å³	0.26 × 0.23 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer	6636 independent reflections
Radiation source: fine-focus sealed tube	5229 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.4°, θ_min = 2.5°
/w and /f scans	h = −9→9
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38	k = −17→17
T_min = 0.782, T_max = 0.857	l = −22→22
27221 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.1018P)² + 0.4601P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6635 reflections	Δρ_max = 0.55 e Å⁻³
458 parameters	Δρ_min = −0.67 e Å⁻³
50 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (4)

Special details top

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

Both ClO₄^- anions are disordered. Anion Cl26—O30 was modelled over two equally occupied orientations, labelled 'A' and 'B'. Anion Cl31—O35 was modelled over three orientations: Cl31A—O35A, occupancy 0.20 Cl31B—O35B, occupancy 0.40 Cl31C—O35C, occupancy 0.40 A l l disordered Cl—O bonds were restrained to 1.43 (2)%A, and non-bonded O···O distances within a given disorder orientation were restrained to 2.34 (2) Å. All non-H atoms with occupancy ≥0.5 were refined anisotropically, while all H atoms were placed in calculated positions and refined using a riding model.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.35715 (5)	0.57370 (3)	0.26333 (2)	0.04755 (18)
N2	0.4880 (4)	0.7309 (2)	0.30282 (15)	0.0503 (6)
C3	0.6607 (5)	0.7681 (3)	0.2815 (2)	0.0552 (7)
C4	0.7607 (6)	0.8804 (3)	0.3107 (2)	0.0684 (9)
H4	0.8834	0.9065	0.2963	0.082*
C5	0.6776 (7)	0.9529 (3)	0.3611 (2)	0.0710 (10)
H5	0.7433	1.0302	0.3818	0.085*
C6	0.5003 (6)	0.9145 (3)	0.3817 (2)	0.0659 (9)
H6	0.4419	0.9645	0.4160	0.079*
C7	0.4086 (5)	0.8021 (3)	0.35176 (19)	0.0533 (7)
C8	0.7301 (5)	0.6813 (3)	0.2275 (2)	0.0603 (8)
H8	0.8505	0.6982	0.2088	0.072*
N9	0.6207 (4)	0.5814 (2)	0.20653 (17)	0.0578 (7)
O10	0.6948 (5)	0.5056 (2)	0.1551 (2)	0.0848 (8)
H10	0.6117	0.4429	0.1383	0.102*
C11	0.2208 (5)	0.7492 (3)	0.3703 (2)	0.0569 (8)
H11	0.1507	0.7916	0.4045	0.068*
N12	0.1571 (4)	0.6445 (2)	0.33857 (16)	0.0535 (6)
O13	−0.0163 (4)	0.6008 (2)	0.35871 (18)	0.0721 (7)
H13	−0.0484	0.5313	0.3377	0.086*
N14	0.2271 (4)	0.4140 (2)	0.22164 (15)	0.0484 (6)
C15	0.1021 (5)	0.3664 (2)	0.14834 (19)	0.0520 (7)
C16	0.0113 (6)	0.2534 (3)	0.1167 (2)	0.0639 (9)
H16	−0.0782	0.2212	0.0652	0.077*
C17	0.0541 (6)	0.1880 (3)	0.1619 (2)	0.0659 (9)
H17	−0.0046	0.1100	0.1411	0.079*
C18	0.1820 (5)	0.2369 (3)	0.2370 (2)	0.0597 (8)
H18	0.2126	0.1929	0.2684	0.072*
C19	0.2651 (5)	0.3503 (2)	0.26615 (19)	0.0509 (7)
C20	0.0700 (5)	0.4423 (3)	0.1055 (2)	0.0583 (8)
H20	−0.0160	0.4160	0.0534	0.070*
N21	0.1605 (4)	0.5442 (2)	0.13992 (16)	0.0549 (6)
O22	0.1211 (5)	0.6091 (2)	0.09440 (16)	0.0751 (8)
H22	0.1775	0.6762	0.1216	0.090*
C23	0.3985 (5)	0.4096 (3)	0.3458 (2)	0.0540 (7)
H23	0.4233	0.3727	0.3835	0.065*
N24	0.4799 (4)	0.5122 (2)	0.36269 (16)	0.0537 (6)
O25	0.6046 (4)	0.5610 (2)	0.43859 (15)	0.0683 (7)
H25	0.6534	0.6288	0.4469	0.082*
Cl26A	0.7803 (10)	0.8476 (5)	0.5464 (4)	0.0532 (15)	0.50
O27A	0.783 (4)	0.771 (2)	0.4668 (10)	0.071 (5)	0.50
O28A	0.5898 (17)	0.8141 (16)	0.5664 (9)	0.085 (3)	0.50
O29A	0.923 (2)	0.8424 (18)	0.6083 (12)	0.090 (4)	0.50
O30A	0.817 (4)	0.9571 (12)	0.5433 (18)	0.070 (4)	0.50
Cl26B	0.7625 (12)	0.8508 (6)	0.5465 (4)	0.068 (2)	0.50
O27B	0.806 (4)	0.788 (2)	0.4684 (10)	0.069 (4)	0.50
O28B	0.5550 (17)	0.8244 (15)	0.5413 (9)	0.083 (3)	0.50
O29B	0.858 (2)	0.824 (2)	0.6105 (12)	0.118 (7)	0.50
O30B	0.841 (4)	0.9672 (13)	0.5584 (18)	0.073 (5)	0.50
Cl31A	0.2073 (14)	0.8941 (5)	0.1455 (5)	0.048 (2)*	0.20
O32A	0.3312 (19)	0.8292 (10)	0.1701 (8)	0.064 (3)*	0.20
O33A	0.262 (3)	1.0011 (11)	0.2191 (9)	0.096 (5)*	0.20
O34A	0.007 (2)	0.841 (2)	0.1338 (16)	0.175 (11)*	0.20
O35A	0.260 (4)	0.921 (2)	0.0789 (11)	0.170 (11)*	0.20
Cl31B	0.2456 (5)	0.8989 (2)	0.1581 (3)	0.0555 (10)*	0.40
O32B	0.2434 (14)	0.8187 (6)	0.1965 (5)	0.070 (2)*	0.40
O33B	0.4310 (15)	0.9600 (10)	0.1701 (7)	0.123 (4)*	0.40
O34B	0.120 (2)	0.9685 (11)	0.2012 (9)	0.148 (4)*	0.40
O35B	0.1271 (15)	0.8526 (8)	0.0748 (5)	0.101 (3)*	0.40
Cl31C	0.1861 (5)	0.8977 (2)	0.1602 (2)	0.0503 (9)*	0.40
O32C	0.1698 (11)	0.8190 (5)	0.1996 (4)	0.0625 (19)*	0.40
O33C	0.3580 (14)	0.9946 (7)	0.1860 (6)	0.093 (2)*	0.40
O34C	0.0216 (15)	0.9302 (10)	0.1600 (7)	0.120 (3)*	0.40
O35C	0.2077 (14)	0.8359 (7)	0.0702 (4)	0.087 (2)*	0.40
O36	−0.1564 (4)	0.3821 (2)	0.29216 (19)	0.0788 (8)
C37	−0.1971 (5)	0.3190 (3)	0.3305 (2)	0.0642 (9)
C38	−0.3147 (7)	0.2016 (3)	0.2852 (3)	0.0754 (10)
H38A	−0.4155	0.1795	0.3160	0.091*
H38B	−0.2277	0.1532	0.2799	0.091*
H38C	−0.3781	0.1949	0.2301	0.091*
C39	−0.1409 (8)	0.3542 (4)	0.4218 (3)	0.0917 (13)
H39A	−0.0501	0.3143	0.4361	0.110*
H39B	−0.2589	0.3372	0.4452	0.110*
H39C	−0.0765	0.4342	0.4444	0.110*
O40	0.4991 (5)	0.2908 (2)	0.10362 (19)	0.0834 (8)
C41	0.4248 (6)	0.2372 (3)	0.0327 (3)	0.0736 (10)
C42	0.3988 (9)	0.2912 (5)	−0.0301 (3)	0.1042 (16)
H42A	0.4434	0.2534	−0.0798	0.125*
H42B	0.4763	0.3694	−0.0075	0.125*
H42C	0.2595	0.2866	−0.0443	0.125*
C43	0.3530 (9)	0.1132 (4)	0.0055 (4)	0.1026 (16)
H43A	0.3860	0.0887	0.0520	0.123*
H43B	0.4160	0.0807	−0.0399	0.123*
H43C	0.2101	0.0891	−0.0134	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0551 (3)	0.0398 (2)	0.0468 (2)	0.01389 (17)	0.00961 (17)	0.01288 (16)
N2	0.0576 (15)	0.0456 (13)	0.0459 (13)	0.0143 (12)	0.0031 (11)	0.0157 (11)
C3	0.0567 (18)	0.0531 (17)	0.0551 (17)	0.0093 (14)	0.0053 (14)	0.0239 (14)
C4	0.068 (2)	0.0563 (19)	0.076 (2)	0.0018 (17)	0.0024 (18)	0.0319 (18)
C5	0.089 (3)	0.0434 (17)	0.072 (2)	0.0057 (18)	−0.002 (2)	0.0229 (16)
C6	0.083 (3)	0.0431 (16)	0.063 (2)	0.0159 (17)	−0.0018 (18)	0.0130 (15)
C7	0.0629 (19)	0.0441 (15)	0.0495 (16)	0.0173 (14)	0.0013 (14)	0.0126 (13)
C8	0.0557 (19)	0.063 (2)	0.065 (2)	0.0137 (16)	0.0156 (15)	0.0256 (17)
N9	0.0602 (17)	0.0552 (16)	0.0587 (16)	0.0163 (13)	0.0149 (13)	0.0188 (13)
O10	0.085 (2)	0.0657 (16)	0.100 (2)	0.0225 (15)	0.0415 (17)	0.0140 (16)
C11	0.067 (2)	0.0449 (16)	0.0553 (17)	0.0219 (15)	0.0099 (15)	0.0083 (13)
N12	0.0595 (16)	0.0479 (14)	0.0516 (14)	0.0180 (12)	0.0112 (12)	0.0124 (11)
O13	0.0715 (17)	0.0557 (14)	0.0827 (18)	0.0148 (13)	0.0259 (14)	0.0133 (13)
N14	0.0544 (15)	0.0434 (13)	0.0482 (13)	0.0143 (11)	0.0125 (11)	0.0151 (10)
C15	0.0598 (18)	0.0429 (15)	0.0492 (16)	0.0150 (14)	0.0079 (13)	0.0102 (12)
C16	0.071 (2)	0.0467 (17)	0.062 (2)	0.0106 (16)	0.0067 (17)	0.0081 (15)
C17	0.080 (2)	0.0382 (15)	0.072 (2)	0.0116 (16)	0.0141 (18)	0.0117 (15)
C18	0.070 (2)	0.0449 (16)	0.069 (2)	0.0189 (15)	0.0184 (17)	0.0223 (15)
C19	0.0572 (18)	0.0440 (15)	0.0554 (17)	0.0183 (13)	0.0150 (14)	0.0179 (13)
C20	0.070 (2)	0.0515 (17)	0.0447 (16)	0.0122 (16)	0.0017 (14)	0.0118 (13)
N21	0.0682 (17)	0.0475 (14)	0.0488 (14)	0.0177 (13)	0.0088 (12)	0.0157 (11)
O22	0.109 (2)	0.0509 (13)	0.0614 (15)	0.0191 (14)	−0.0030 (14)	0.0218 (12)
C23	0.0622 (19)	0.0491 (16)	0.0557 (17)	0.0189 (15)	0.0107 (14)	0.0228 (14)
N24	0.0625 (16)	0.0495 (14)	0.0516 (14)	0.0182 (12)	0.0112 (12)	0.0187 (11)
O25	0.0787 (17)	0.0569 (14)	0.0584 (14)	0.0056 (13)	0.0004 (12)	0.0189 (11)
Cl26A	0.0538 (19)	0.043 (2)	0.063 (3)	0.0102 (15)	0.0145 (16)	0.0197 (18)
O27A	0.102 (9)	0.048 (8)	0.052 (6)	0.006 (5)	0.022 (5)	0.011 (4)
O28A	0.074 (6)	0.092 (6)	0.095 (9)	0.023 (5)	0.039 (6)	0.035 (6)
O29A	0.104 (7)	0.092 (5)	0.080 (8)	0.026 (6)	−0.002 (6)	0.045 (5)
O30A	0.095 (10)	0.042 (5)	0.064 (9)	0.015 (6)	0.010 (7)	0.011 (5)
Cl26B	0.099 (5)	0.069 (3)	0.043 (3)	0.037 (3)	0.018 (2)	0.0158 (19)
O27B	0.095 (9)	0.045 (7)	0.068 (7)	0.023 (8)	0.030 (5)	0.013 (4)
O28B	0.081 (6)	0.078 (6)	0.083 (8)	0.007 (4)	0.026 (5)	0.024 (5)
O29B	0.176 (15)	0.154 (17)	0.064 (6)	0.094 (14)	0.034 (9)	0.055 (9)
O30B	0.076 (6)	0.052 (6)	0.066 (9)	−0.004 (4)	0.003 (5)	0.004 (4)
O36	0.0864 (19)	0.0549 (14)	0.093 (2)	0.0145 (13)	0.0327 (16)	0.0206 (14)
C37	0.059 (2)	0.0565 (19)	0.078 (2)	0.0197 (16)	0.0179 (17)	0.0193 (18)
C38	0.080 (3)	0.058 (2)	0.081 (3)	0.0086 (19)	0.015 (2)	0.0218 (19)
C39	0.095 (3)	0.079 (3)	0.086 (3)	0.018 (2)	−0.001 (2)	0.017 (2)
O40	0.100 (2)	0.0688 (17)	0.0768 (19)	0.0228 (15)	0.0171 (16)	0.0181 (15)
C41	0.071 (2)	0.067 (2)	0.082 (3)	0.0231 (19)	0.024 (2)	0.018 (2)
C42	0.125 (4)	0.105 (4)	0.088 (3)	0.031 (3)	0.024 (3)	0.039 (3)
C43	0.117 (4)	0.067 (3)	0.109 (4)	0.025 (3)	0.028 (3)	0.009 (3)

Geometric parameters (Å, º) top

Cu1—N2	1.930 (3)	C23—H23	0.9500
Cu1—N14	1.956 (3)	N24—O25	1.378 (4)
Cu1—N9	2.205 (3)	O25—H25	0.8400
Cu1—N12	2.206 (3)	Cl26A—O30A	1.423 (11)
Cu1—N24	2.289 (3)	Cl26A—O29A	1.427 (12)
Cu1—N21	2.298 (3)	Cl26A—O28A	1.438 (11)
N2—C7	1.335 (4)	Cl26A—O27A	1.443 (12)
N2—C3	1.347 (4)	Cl26B—O29B	1.416 (12)
C3—C4	1.389 (5)	Cl26B—O28B	1.424 (12)
C3—C8	1.461 (5)	Cl26B—O30B	1.446 (12)
C4—C5	1.374 (6)	Cl26B—O27B	1.459 (11)
C4—H4	0.9500	Cl31A—O35A	1.368 (14)
C5—C6	1.372 (6)	Cl31A—O34A	1.399 (15)
C5—H5	0.9500	Cl31A—O32A	1.479 (11)
C6—C7	1.377 (5)	Cl31A—O33A	1.519 (12)
C6—H6	0.9500	Cl31B—O33B	1.334 (10)
C7—C11	1.472 (5)	Cl31B—O32B	1.407 (7)
C8—N9	1.281 (4)	Cl31B—O35B	1.458 (9)
C8—H8	0.9500	Cl31B—O34B	1.517 (11)
N9—O10	1.369 (4)	Cl31C—O34C	1.339 (9)
O10—H10	0.8400	Cl31C—O32C	1.394 (7)
C11—N12	1.266 (4)	Cl31C—O33C	1.461 (8)
C11—H11	0.9500	Cl31C—O35C	1.564 (8)
N12—O13	1.363 (4)	O36—C37	1.216 (5)
O13—H13	0.8400	C37—C39	1.485 (6)
N14—C15	1.346 (4)	C37—C38	1.492 (5)
N14—C19	1.352 (4)	C38—H38A	0.9800
C15—C16	1.383 (4)	C38—H38B	0.9800
C15—C20	1.458 (4)	C38—H38C	0.9800
C16—C17	1.390 (5)	C39—H39A	0.9800
C16—H16	0.9500	C39—H39B	0.9800
C17—C18	1.379 (5)	C39—H39C	0.9800
C17—H17	0.9500	O40—C41	1.202 (5)
C18—C19	1.379 (4)	C41—C42	1.487 (7)
C18—H18	0.9500	C41—C43	1.497 (6)
C19—C23	1.460 (5)	C42—H42A	0.9800
C20—N21	1.265 (4)	C42—H42B	0.9800
C20—H20	0.9500	C42—H42C	0.9800
N21—O22	1.380 (3)	C43—H43A	0.9800
O22—H22	0.8400	C43—H43B	0.9800
C23—N24	1.267 (4)	C43—H43C	0.9800

N2—Cu1—N14	178.96 (10)	O22—N21—Cu1	136.0 (2)
N2—Cu1—N9	77.58 (11)	N21—O22—H22	109.5
N14—Cu1—N9	101.46 (11)	N24—C23—C19	117.5 (3)
N2—Cu1—N12	77.24 (11)	N24—C23—H23	121.3
N14—Cu1—N12	103.72 (10)	C19—C23—H23	121.3
N9—Cu1—N12	154.81 (11)	C23—N24—O25	113.4 (3)
N2—Cu1—N24	104.19 (10)	C23—N24—Cu1	110.6 (2)
N14—Cu1—N24	76.22 (10)	O25—N24—Cu1	135.68 (19)
N9—Cu1—N24	93.82 (10)	N24—O25—H25	109.5
N12—Cu1—N24	92.92 (10)	O30A—Cl26A—O29A	110.8 (10)
N2—Cu1—N21	103.90 (10)	O30A—Cl26A—O28A	110.2 (11)
N14—Cu1—N21	75.69 (10)	O29A—Cl26A—O28A	107.9 (9)
N9—Cu1—N21	91.63 (11)	O30A—Cl26A—O27A	109.9 (11)
N12—Cu1—N21	93.77 (10)	O29A—Cl26A—O27A	109.8 (11)
N24—Cu1—N21	151.90 (10)	O28A—Cl26A—O27A	108.2 (11)
C7—N2—C3	120.3 (3)	O29B—Cl26B—O28B	112.2 (9)
C7—N2—Cu1	120.1 (2)	O29B—Cl26B—O30B	110.2 (11)
C3—N2—Cu1	119.6 (2)	O28B—Cl26B—O30B	109.9 (11)
N2—C3—C4	120.8 (3)	O29B—Cl26B—O27B	108.1 (11)
N2—C3—C8	114.5 (3)	O28B—Cl26B—O27B	109.3 (10)
C4—C3—C8	124.7 (3)	O30B—Cl26B—O27B	106.9 (11)
C5—C4—C3	118.4 (4)	O35A—Cl31A—O34A	113.3 (13)
C5—C4—H4	120.8	O35A—Cl31A—O32A	110.8 (12)
C3—C4—H4	120.8	O34A—Cl31A—O32A	111.9 (11)
C6—C5—C4	120.4 (3)	O35A—Cl31A—O33A	107.4 (11)
C6—C5—H5	119.8	O34A—Cl31A—O33A	109.3 (12)
C4—C5—H5	119.8	O32A—Cl31A—O33A	103.5 (8)
C5—C6—C7	118.8 (4)	O33B—Cl31B—O32B	108.3 (6)
C5—C6—H6	120.6	O33B—Cl31B—O35B	119.2 (7)
C7—C6—H6	120.6	O32B—Cl31B—O35B	112.7 (5)
N2—C7—C6	121.3 (3)	O33B—Cl31B—O34B	111.1 (8)
N2—C7—C11	114.1 (3)	O32B—Cl31B—O34B	105.2 (7)
C6—C7—C11	124.7 (3)	O35B—Cl31B—O34B	99.2 (7)
N9—C8—C3	116.8 (3)	O34C—Cl31C—O32C	108.4 (6)
N9—C8—H8	121.6	O34C—Cl31C—O33C	109.8 (6)
C3—C8—H8	121.6	O32C—Cl31C—O33C	120.6 (5)
C8—N9—O10	113.1 (3)	O34C—Cl31C—O35C	111.0 (6)
C8—N9—Cu1	111.5 (2)	O32C—Cl31C—O35C	105.2 (5)
O10—N9—Cu1	135.4 (2)	O33C—Cl31C—O35C	101.4 (5)
N9—O10—H10	109.5	O36—C37—C39	123.0 (4)
N12—C11—C7	116.9 (3)	O36—C37—C38	119.4 (4)
N12—C11—H11	121.6	C39—C37—C38	117.6 (4)
C7—C11—H11	121.6	C37—C38—H38A	109.5
C11—N12—O13	113.9 (3)	C37—C38—H38B	109.5
C11—N12—Cu1	111.7 (2)	H38A—C38—H38B	109.5
O13—N12—Cu1	134.4 (2)	C37—C38—H38C	109.5
N12—O13—H13	109.5	H38A—C38—H38C	109.5
C15—N14—C19	119.5 (3)	H38B—C38—H38C	109.5
C15—N14—Cu1	120.7 (2)	C37—C39—H39A	109.5
C19—N14—Cu1	119.9 (2)	C37—C39—H39B	109.5
N14—C15—C16	121.8 (3)	H39A—C39—H39B	109.5
N14—C15—C20	115.3 (3)	C37—C39—H39C	109.5
C16—C15—C20	122.9 (3)	H39A—C39—H39C	109.5
C15—C16—C17	118.4 (3)	H39B—C39—H39C	109.5
C15—C16—H16	120.8	O40—C41—C42	121.4 (4)
C17—C16—H16	120.8	O40—C41—C43	120.4 (4)
C18—C17—C16	119.7 (3)	C42—C41—C43	118.1 (4)
C18—C17—H17	120.2	C41—C42—H42A	109.5
C16—C17—H17	120.2	C41—C42—H42B	109.5
C19—C18—C17	119.3 (3)	H42A—C42—H42B	109.5
C19—C18—H18	120.4	C41—C42—H42C	109.5
C17—C18—H18	120.4	H42A—C42—H42C	109.5
N14—C19—C18	121.3 (3)	H42B—C42—H42C	109.5
N14—C19—C23	115.6 (3)	C41—C43—H43A	109.5
C18—C19—C23	123.1 (3)	C41—C43—H43B	109.5
N21—C20—C15	117.8 (3)	H43A—C43—H43B	109.5
N21—C20—H20	121.1	C41—C43—H43C	109.5
C15—C20—H20	121.1	H43A—C43—H43C	109.5
C20—N21—O22	113.4 (3)	H43B—C43—H43C	109.5
C20—N21—Cu1	110.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.84	1.85	2.664 (4)	162
O13—H13···O36	0.84	1.82	2.648 (4)	171
O22—H22···O32A	0.84	1.93	2.759 (13)	171
O22—H22···O32B	0.84	1.84	2.662 (8)	164
O22—H22···O32C	0.84	1.97	2.727 (7)	149
O22—H22···O35A	0.84	3.46	4.10 (2)	135
O22—H22···O35B	0.84	2.77	3.319 (10)	125
O22—H22···O35C	0.84	2.50	3.073 (9)	127
O25—H25···O27A	0.84	1.79	2.63 (3)	174
O25—H25···O27B	0.84	2.03	2.86 (3)	172

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh68200) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.611 Mg m⁻³
a = 7.0855 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1506 (5) Å	Cell parameters from 24551 reflections
c = 17.2510 (8) Å	θ = 3.0–27.5°
α = 107.936 (3)°	µ = 1.01 mm⁻¹
β = 95.762 (2)°	T = 200 K
γ = 103.4315 (15)°	Rectangular prism, green
V = 1461.57 (11) Å³	0.26 × 0.23 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer	6483 independent reflections
Radiation source: fine-focus sealed tube	4699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
/w and /f scans	h = −9→9
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38	k = −17→17
T_min = 0.780, T_max = 0.856	l = −22→22
24551 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.0967P)² + 0.4298P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6483 reflections	Δρ_max = 0.81 e Å⁻³
413 parameters	Δρ_min = −0.62 e Å⁻³
30 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Special details top

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

The ClO₄^- anion Cl31—O35 is disordered, and was modelled over three orientations: Cl31A—O35A, occupancy 0.30 Cl31B—O35B, occupancy 0.30 Cl31C—O35C, occupancy 0.40 A l l disordered Cl—O bonds were restrained to 1.43 (2)%A, and non-bonded O···O distances within a given disorder orientation were restrained to 2.34 (2) Å. All non-H atoms except for the disordered anion were refined anisotropically, while all H atoms were placed in calculated positions and refined using a riding model.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.36152 (6)	0.57336 (3)	0.26340 (2)	0.04165 (18)
N2	0.4930 (4)	0.7304 (2)	0.30285 (16)	0.0426 (6)
C3	0.6668 (6)	0.7676 (3)	0.2808 (2)	0.0484 (8)
C4	0.7668 (7)	0.8793 (3)	0.3092 (2)	0.0578 (10)
H4	0.8896	0.9048	0.2941	0.069*
C5	0.6837 (7)	0.9530 (3)	0.3604 (2)	0.0598 (10)
H5	0.7496	1.0303	0.3807	0.072*
C6	0.5055 (6)	0.9148 (3)	0.3821 (2)	0.0559 (10)
H6	0.4473	0.9653	0.4169	0.067*
C7	0.4132 (6)	0.8023 (3)	0.3523 (2)	0.0477 (8)
C8	0.7355 (6)	0.6801 (3)	0.2263 (2)	0.0518 (8)
H8	0.8560	0.6965	0.2070	0.062*
N9	0.6252 (5)	0.5799 (2)	0.20567 (18)	0.0488 (7)
O10	0.6993 (5)	0.5034 (2)	0.1539 (2)	0.0709 (8)
H10	0.6181	0.4402	0.1391	0.085*
C11	0.2259 (6)	0.7497 (3)	0.3709 (2)	0.0486 (8)
H11	0.1554	0.7924	0.4054	0.058*
N12	0.1620 (5)	0.6451 (2)	0.33912 (17)	0.0454 (7)
O13	−0.0129 (4)	0.6010 (2)	0.35984 (18)	0.0610 (7)
H13	−0.0398	0.5312	0.3421	0.073*
N14	0.2314 (4)	0.4136 (2)	0.22238 (16)	0.0412 (6)
C15	0.1056 (6)	0.3657 (3)	0.1485 (2)	0.0459 (8)
C16	0.0122 (6)	0.2526 (3)	0.1175 (2)	0.0538 (9)
H16	−0.0797	0.2205	0.0666	0.065*
C17	0.0561 (6)	0.1871 (3)	0.1627 (2)	0.0560 (9)
H17	−0.0027	0.1090	0.1418	0.067*
C18	0.1845 (6)	0.2353 (3)	0.2374 (2)	0.0512 (9)
H18	0.2146	0.1911	0.2687	0.061*
C19	0.2703 (5)	0.3504 (3)	0.2669 (2)	0.0448 (8)
C20	0.0729 (6)	0.4410 (3)	0.1050 (2)	0.0490 (8)
H20	−0.0127	0.4143	0.0527	0.059*
N21	0.1634 (5)	0.5438 (2)	0.13989 (17)	0.0481 (7)
O22	0.1243 (5)	0.6080 (2)	0.09351 (16)	0.0641 (8)
H22	0.1624	0.6755	0.1234	0.077*
C23	0.4028 (5)	0.4090 (3)	0.3460 (2)	0.0466 (8)
H23	0.4281	0.3715	0.3833	0.056*
N24	0.4840 (4)	0.5122 (2)	0.36386 (17)	0.0455 (7)
O25	0.6093 (4)	0.5606 (2)	0.43922 (15)	0.0578 (7)
H25	0.6475	0.6298	0.4501	0.069*
Cl26	0.77202 (15)	0.85049 (7)	0.54636 (5)	0.0519 (3)
O27	0.7967 (5)	0.7797 (2)	0.46750 (16)	0.0609 (7)
O28	0.5703 (6)	0.8197 (3)	0.5532 (2)	0.0927 (12)
O29	0.8951 (7)	0.8374 (3)	0.6108 (2)	0.0962 (12)
O30	0.8276 (5)	0.9636 (2)	0.55053 (18)	0.0636 (7)
Cl31A	0.2432 (9)	0.8946 (3)	0.1485 (3)	0.0404 (11)*	0.30
O32A	0.3009 (18)	0.8230 (8)	0.1834 (7)	0.074 (3)*	0.30
O33A	0.4056 (18)	0.9831 (10)	0.1608 (9)	0.091 (4)*	0.30
O34A	0.084 (2)	0.9507 (11)	0.1817 (8)	0.079 (3)*	0.30
O35A	0.1449 (19)	0.8339 (10)	0.0673 (6)	0.063 (3)*	0.30
Cl31B	0.2317 (11)	0.9006 (4)	0.1657 (3)	0.0456 (15)*	0.30
O32B	0.165 (2)	0.8148 (10)	0.1971 (8)	0.068 (5)*	0.30
O33B	0.4401 (16)	0.9489 (11)	0.1774 (8)	0.089 (4)*	0.30
O34B	0.183 (3)	0.9951 (11)	0.2211 (9)	0.118 (5)*	0.30
O35B	0.137 (3)	0.8779 (17)	0.0834 (9)	0.159 (9)*	0.30
Cl31C	0.1875 (5)	0.8949 (2)	0.1539 (3)	0.0412 (9)*	0.40
O32C	0.2182 (17)	0.8205 (6)	0.2009 (5)	0.043 (2)*	0.40
O33C	0.3470 (15)	0.9965 (7)	0.1926 (6)	0.088 (3)*	0.40
O34C	0.0081 (17)	0.9114 (12)	0.1513 (9)	0.131 (5)*	0.40
O35C	0.2279 (16)	0.8391 (7)	0.0704 (5)	0.075 (3)*	0.40
O36	−0.1544 (5)	0.3826 (2)	0.29118 (18)	0.0654 (8)
C37	−0.1958 (6)	0.3183 (3)	0.3295 (2)	0.0546 (9)
C38	−0.3140 (7)	0.2011 (3)	0.2844 (3)	0.0627 (10)
H38A	−0.4185	0.1803	0.3144	0.075*
H38B	−0.2279	0.1519	0.2806	0.075*
H38C	−0.3734	0.1939	0.2285	0.075*
C39	−0.1361 (8)	0.3541 (4)	0.4216 (3)	0.0756 (13)
H39A	−0.0188	0.3309	0.4350	0.091*
H39B	−0.2444	0.3196	0.4445	0.091*
H39C	−0.1060	0.4352	0.4456	0.091*
O40	0.5021 (5)	0.2877 (2)	0.10283 (18)	0.0685 (8)
C41	0.4259 (7)	0.2352 (4)	0.0322 (3)	0.0639 (10)
C42	0.3981 (9)	0.2905 (5)	−0.0308 (3)	0.0878 (15)
H42A	0.4488	0.2552	−0.0800	0.105*
H42B	0.4701	0.3696	−0.0070	0.105*
H42C	0.2572	0.2826	−0.0465	0.105*
C43	0.3460 (9)	0.1092 (4)	0.0038 (3)	0.0880 (15)
H43A	0.3659	0.0841	0.0511	0.106*
H43B	0.4160	0.0749	−0.0388	0.106*
H43C	0.2046	0.0873	−0.0194	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0472 (3)	0.0347 (2)	0.0424 (3)	0.01151 (18)	0.00859 (18)	0.01195 (17)
N2	0.0455 (17)	0.0404 (14)	0.0418 (14)	0.0113 (12)	0.0033 (12)	0.0159 (11)
C3	0.051 (2)	0.0464 (18)	0.0463 (18)	0.0087 (16)	0.0026 (16)	0.0198 (15)
C4	0.063 (3)	0.050 (2)	0.058 (2)	0.0030 (18)	0.0047 (19)	0.0256 (17)
C5	0.075 (3)	0.0365 (18)	0.059 (2)	0.0034 (18)	−0.003 (2)	0.0181 (16)
C6	0.071 (3)	0.0399 (18)	0.052 (2)	0.0161 (18)	−0.0003 (18)	0.0126 (16)
C7	0.058 (2)	0.0413 (17)	0.0427 (17)	0.0166 (16)	0.0028 (16)	0.0133 (14)
C8	0.045 (2)	0.057 (2)	0.057 (2)	0.0114 (17)	0.0126 (16)	0.0251 (17)
N9	0.0526 (19)	0.0466 (16)	0.0502 (16)	0.0164 (14)	0.0145 (14)	0.0171 (13)
O10	0.072 (2)	0.0538 (16)	0.084 (2)	0.0184 (15)	0.0338 (17)	0.0140 (15)
C11	0.057 (2)	0.0422 (18)	0.0458 (18)	0.0192 (16)	0.0096 (16)	0.0094 (14)
N12	0.0509 (18)	0.0396 (14)	0.0466 (15)	0.0169 (13)	0.0103 (13)	0.0124 (12)
O13	0.0589 (18)	0.0478 (14)	0.0719 (17)	0.0114 (13)	0.0229 (14)	0.0136 (13)
N14	0.0442 (16)	0.0363 (13)	0.0439 (14)	0.0128 (12)	0.0090 (12)	0.0136 (11)
C15	0.051 (2)	0.0378 (16)	0.0455 (17)	0.0130 (15)	0.0088 (15)	0.0088 (14)
C16	0.058 (2)	0.0401 (17)	0.053 (2)	0.0092 (17)	0.0040 (17)	0.0075 (15)
C17	0.064 (3)	0.0300 (16)	0.066 (2)	0.0069 (16)	0.0148 (19)	0.0087 (15)
C18	0.060 (2)	0.0372 (16)	0.061 (2)	0.0170 (16)	0.0177 (18)	0.0182 (15)
C19	0.051 (2)	0.0376 (16)	0.0501 (18)	0.0160 (15)	0.0139 (15)	0.0163 (14)
C20	0.057 (2)	0.0425 (18)	0.0421 (17)	0.0125 (16)	0.0031 (16)	0.0092 (14)
N21	0.0553 (19)	0.0429 (15)	0.0463 (15)	0.0157 (14)	0.0063 (13)	0.0149 (12)
O22	0.091 (2)	0.0422 (13)	0.0565 (15)	0.0150 (14)	−0.0016 (14)	0.0204 (12)
C23	0.052 (2)	0.0429 (17)	0.0516 (19)	0.0164 (16)	0.0120 (16)	0.0231 (15)
N24	0.0493 (18)	0.0433 (15)	0.0447 (15)	0.0140 (13)	0.0095 (13)	0.0152 (12)
O25	0.0637 (18)	0.0491 (14)	0.0526 (14)	0.0050 (13)	0.0011 (13)	0.0170 (12)
Cl26	0.0635 (6)	0.0463 (5)	0.0469 (5)	0.0157 (4)	0.0145 (4)	0.0159 (4)
O27	0.078 (2)	0.0486 (14)	0.0539 (14)	0.0162 (14)	0.0221 (14)	0.0127 (11)
O28	0.083 (3)	0.0666 (19)	0.116 (3)	0.0053 (18)	0.052 (2)	0.0150 (19)
O29	0.141 (4)	0.100 (3)	0.0615 (19)	0.052 (3)	0.005 (2)	0.0379 (18)
O30	0.072 (2)	0.0419 (13)	0.0696 (17)	0.0090 (13)	0.0147 (14)	0.0143 (12)
O36	0.071 (2)	0.0471 (14)	0.0766 (18)	0.0130 (14)	0.0272 (15)	0.0182 (14)
C37	0.047 (2)	0.050 (2)	0.067 (2)	0.0177 (17)	0.0149 (18)	0.0166 (18)
C38	0.066 (3)	0.049 (2)	0.065 (2)	0.0050 (19)	0.010 (2)	0.0171 (18)
C39	0.077 (3)	0.064 (3)	0.072 (3)	0.014 (2)	−0.003 (2)	0.013 (2)
O40	0.076 (2)	0.0592 (17)	0.0647 (18)	0.0171 (15)	0.0114 (15)	0.0161 (14)
C41	0.067 (3)	0.057 (2)	0.068 (3)	0.020 (2)	0.018 (2)	0.019 (2)
C42	0.099 (4)	0.087 (3)	0.081 (3)	0.023 (3)	0.016 (3)	0.035 (3)
C43	0.100 (4)	0.059 (3)	0.095 (4)	0.021 (3)	0.028 (3)	0.009 (2)

Geometric parameters (Å, º) top

Cu1—N2	1.925 (3)	O22—H22	0.8400
Cu1—N14	1.954 (3)	C23—N24	1.269 (4)
Cu1—N12	2.197 (3)	C23—H23	0.9500
Cu1—N9	2.200 (3)	N24—O25	1.371 (4)
Cu1—N24	2.299 (3)	O25—H25	0.8400
Cu1—N21	2.302 (3)	Cl26—O28	1.419 (4)
N2—C7	1.338 (4)	Cl26—O29	1.420 (3)
N2—C3	1.353 (5)	Cl26—O30	1.424 (3)
C3—C4	1.380 (5)	Cl26—O27	1.446 (3)
C3—C8	1.459 (5)	Cl31A—O32A	1.378 (10)
C4—C5	1.382 (6)	Cl31A—O33A	1.379 (11)
C4—H4	0.9500	Cl31A—O35A	1.393 (10)
C5—C6	1.379 (6)	Cl31A—O34A	1.547 (10)
C5—H5	0.9500	Cl31B—O32B	1.402 (10)
C6—C7	1.377 (5)	Cl31B—O35B	1.418 (13)
C6—H6	0.9500	Cl31B—O33B	1.432 (12)
C7—C11	1.463 (5)	Cl31B—O34B	1.452 (12)
C8—N9	1.285 (5)	Cl31C—O34C	1.337 (10)
C8—H8	0.9500	Cl31C—O33C	1.451 (9)
N9—O10	1.368 (4)	Cl31C—O32C	1.488 (7)
O10—H10	0.8400	Cl31C—O35C	1.491 (8)
C11—N12	1.263 (4)	O36—C37	1.227 (5)
C11—H11	0.9500	C37—C38	1.487 (5)
N12—O13	1.372 (4)	C37—C39	1.495 (6)
O13—H13	0.8400	C38—H38A	0.9800
N14—C19	1.346 (4)	C38—H38B	0.9800
N14—C15	1.354 (4)	C38—H38C	0.9800
C15—C16	1.385 (5)	C39—H39A	0.9800
C15—C20	1.457 (5)	C39—H39B	0.9800
C16—C17	1.390 (5)	C39—H39C	0.9800
C16—H16	0.9500	O40—C41	1.195 (5)
C17—C18	1.373 (6)	C41—C42	1.503 (7)
C17—H17	0.9500	C41—C43	1.522 (6)
C18—C19	1.398 (5)	C42—H42A	0.9800
C18—H18	0.9500	C42—H42B	0.9800
C19—C23	1.448 (5)	C42—H42C	0.9800
C20—N21	1.273 (4)	C43—H43A	0.9800
C20—H20	0.9500	C43—H43B	0.9800
N21—O22	1.382 (4)	C43—H43C	0.9800

N2—Cu1—N14	179.09 (12)	C15—C20—H20	121.3
N2—Cu1—N12	77.16 (11)	C20—N21—O22	113.1 (3)
N14—Cu1—N12	103.75 (11)	C20—N21—Cu1	110.5 (2)
N2—Cu1—N9	77.65 (11)	O22—N21—Cu1	136.4 (2)
N14—Cu1—N9	101.43 (11)	N21—O22—H22	109.5
N12—Cu1—N9	154.80 (11)	N24—C23—C19	117.8 (3)
N2—Cu1—N24	103.98 (11)	N24—C23—H23	121.1
N14—Cu1—N24	76.04 (11)	C19—C23—H23	121.1
N12—Cu1—N24	92.55 (10)	C23—N24—O25	113.9 (3)
N9—Cu1—N24	94.22 (11)	C23—N24—Cu1	110.0 (2)
N2—Cu1—N21	103.99 (11)	O25—N24—Cu1	135.9 (2)
N14—Cu1—N21	75.99 (11)	N24—O25—H25	109.5
N12—Cu1—N21	93.73 (11)	O28—Cl26—O29	111.1 (3)
N9—Cu1—N21	91.59 (11)	O28—Cl26—O30	109.2 (2)
N24—Cu1—N21	152.03 (10)	O29—Cl26—O30	109.5 (2)
C7—N2—C3	120.1 (3)	O28—Cl26—O27	108.7 (2)
C7—N2—Cu1	120.1 (2)	O29—Cl26—O27	108.6 (2)
C3—N2—Cu1	119.7 (2)	O30—Cl26—O27	109.67 (17)
N2—C3—C4	121.2 (3)	O32A—Cl31A—O33A	108.1 (8)
N2—C3—C8	114.2 (3)	O32A—Cl31A—O35A	108.6 (7)
C4—C3—C8	124.5 (4)	O33A—Cl31A—O35A	117.8 (8)
C3—C4—C5	118.2 (4)	O32A—Cl31A—O34A	119.5 (7)
C3—C4—H4	120.9	O33A—Cl31A—O34A	103.7 (8)
C5—C4—H4	120.9	O35A—Cl31A—O34A	99.5 (8)
C6—C5—C4	120.3 (3)	O32B—Cl31B—O35B	113.8 (10)
C6—C5—H5	119.8	O32B—Cl31B—O33B	118.3 (9)
C4—C5—H5	119.8	O35B—Cl31B—O33B	111.4 (10)
C7—C6—C5	118.9 (4)	O32B—Cl31B—O34B	104.0 (8)
C7—C6—H6	120.6	O35B—Cl31B—O34B	109.3 (10)
C5—C6—H6	120.6	O33B—Cl31B—O34B	98.2 (8)
N2—C7—C6	121.2 (4)	O34C—Cl31C—O33C	113.5 (7)
N2—C7—C11	113.8 (3)	O34C—Cl31C—O32C	113.4 (7)
C6—C7—C11	125.0 (3)	O33C—Cl31C—O32C	105.3 (6)
N9—C8—C3	116.8 (3)	O34C—Cl31C—O35C	113.2 (7)
N9—C8—H8	121.6	O33C—Cl31C—O35C	106.9 (6)
C3—C8—H8	121.6	O32C—Cl31C—O35C	103.8 (5)
C8—N9—O10	113.0 (3)	O36—C37—C38	119.8 (4)
C8—N9—Cu1	111.5 (2)	O36—C37—C39	122.3 (4)
O10—N9—Cu1	135.5 (2)	C38—C37—C39	117.9 (4)
N9—O10—H10	109.5	C37—C38—H38A	109.5
N12—C11—C7	117.0 (3)	C37—C38—H38B	109.5
N12—C11—H11	121.5	H38A—C38—H38B	109.5
C7—C11—H11	121.5	C37—C38—H38C	109.5
C11—N12—O13	114.1 (3)	H38A—C38—H38C	109.5
C11—N12—Cu1	111.9 (2)	H38B—C38—H38C	109.5
O13—N12—Cu1	134.0 (2)	C37—C39—H39A	109.5
N12—O13—H13	109.5	C37—C39—H39B	109.5
C19—N14—C15	119.8 (3)	H39A—C39—H39B	109.5
C19—N14—Cu1	119.9 (2)	C37—C39—H39C	109.5
C15—N14—Cu1	120.3 (2)	H39A—C39—H39C	109.5
N14—C15—C16	121.6 (3)	H39B—C39—H39C	109.5
N14—C15—C20	115.7 (3)	O40—C41—C42	121.9 (4)
C16—C15—C20	122.7 (3)	O40—C41—C43	120.6 (4)
C15—C16—C17	118.5 (3)	C42—C41—C43	117.5 (4)
C15—C16—H16	120.8	C41—C42—H42A	109.5
C17—C16—H16	120.8	C41—C42—H42B	109.5
C18—C17—C16	120.1 (3)	H42A—C42—H42B	109.5
C18—C17—H17	120.0	C41—C42—H42C	109.5
C16—C17—H17	120.0	H42A—C42—H42C	109.5
C17—C18—C19	119.1 (3)	H42B—C42—H42C	109.5
C17—C18—H18	120.5	C41—C43—H43A	109.5
C19—C18—H18	120.5	C41—C43—H43B	109.5
N14—C19—C18	120.9 (3)	H43A—C43—H43B	109.5
N14—C19—C23	116.0 (3)	C41—C43—H43C	109.5
C18—C19—C23	123.1 (3)	H43A—C43—H43C	109.5
N21—C20—C15	117.5 (3)	H43B—C43—H43C	109.5
N21—C20—H20	121.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.84	1.86	2.674 (4)	164
O13—H13···O36	0.84	1.82	2.644 (4)	166
O22—H22···O32A	0.84	1.86	2.689 (11)	167
O22—H22···O32B	0.84	1.87	2.685 (13)	162
O22—H22···O32C	0.84	1.88	2.717 (8)	171
O22—H22···O35A	0.84	2.57	3.113 (12)	123
O22—H22···O35B	0.84	2.99	3.59 (2)	130
O22—H22···O35C	0.84	2.55	3.114 (9)	125
O25—H25···O27	0.84	1.92	2.743 (4)	165

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh68150) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.634 Mg m⁻³
a = 6.8970 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1061 (3) Å	Cell parameters from 28604 reflections
c = 17.5747 (5) Å	θ = 3.1–27.5°
α = 107.2954 (16)°	µ = 1.02 mm⁻¹
β = 94.5678 (12)°	T = 150 K
γ = 105.3383 (11)°	Rectangular prism, green
V = 1441.00 (7) Å³	0.26 × 0.23 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer	6556 independent reflections
Radiation source: fine-focus sealed tube	5328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
/w and /f scans	h = −8→8
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38	k = −17→16
T_min = 0.777, T_max = 0.854	l = −22→22
28604 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0495P)² + 0.540P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
6556 reflections	Δρ_max = 0.37 e Å⁻³
407 parameters	Δρ_min = −0.64 e Å⁻³
4 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (14)

Special details top

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

There is no disorder in this structure. All non-H atoms were refined anisotropically. All C-bound H atoms were placed in calculated positions, and refined using a riding model. All O—H H atoms were located in the difference map, then allowed to refine with a common thermal parameter subject to the restraint O—H = 0.79 (2) Å.

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

	x	y	z	U_iso*/U_eq
Cu1	0.35659 (4)	0.57945 (2)	0.260696 (15)	0.03068 (11)
N2	0.5066 (3)	0.73676 (15)	0.29751 (11)	0.0319 (4)
C3	0.6865 (3)	0.77130 (19)	0.27403 (13)	0.0346 (5)
C4	0.8008 (4)	0.8834 (2)	0.30094 (15)	0.0403 (5)
H4	0.9279	0.9073	0.2843	0.048*
C5	0.7245 (4)	0.95970 (19)	0.35294 (15)	0.0413 (5)
H5	0.8008	1.0369	0.3728	0.050*
C6	0.5388 (4)	0.92436 (19)	0.37607 (14)	0.0386 (5)
H6	0.4852	0.9766	0.4111	0.046*
C7	0.4318 (3)	0.81086 (18)	0.34712 (13)	0.0335 (5)
C8	0.7432 (3)	0.68023 (19)	0.21885 (14)	0.0364 (5)
H8	0.8657	0.6937	0.1972	0.044*
N9	0.6192 (3)	0.58126 (16)	0.20123 (12)	0.0361 (4)
O10	0.6792 (3)	0.50081 (15)	0.14700 (12)	0.0513 (5)
H10	0.603 (4)	0.441 (2)	0.1418 (19)	0.057 (5)*
C11	0.2356 (3)	0.75985 (18)	0.36730 (13)	0.0348 (5)
H11	0.1671	0.8033	0.4020	0.042*
N12	0.1617 (3)	0.65310 (15)	0.33538 (11)	0.0330 (4)
O13	−0.0208 (3)	0.61008 (14)	0.35704 (11)	0.0437 (4)
H13	−0.055 (5)	0.5447 (19)	0.3364 (18)	0.057 (5)*
N14	0.2092 (3)	0.41776 (14)	0.22205 (10)	0.0298 (4)
C15	0.0788 (3)	0.37023 (18)	0.15056 (13)	0.0322 (5)
C16	−0.0271 (4)	0.25695 (19)	0.12205 (14)	0.0370 (5)
H16	−0.1206	0.2253	0.0724	0.044*
C17	0.0056 (4)	0.19044 (19)	0.16708 (14)	0.0381 (5)
H17	−0.0644	0.1123	0.1482	0.046*
C18	0.1407 (4)	0.23860 (18)	0.23963 (14)	0.0358 (5)
H18	0.1664	0.1938	0.2706	0.043*
C19	0.2379 (3)	0.35319 (18)	0.26644 (13)	0.0313 (4)
C20	0.0570 (3)	0.44518 (18)	0.10544 (13)	0.0343 (5)
H20	−0.0278	0.4177	0.0539	0.041*
N21	0.1560 (3)	0.54851 (15)	0.13789 (11)	0.0335 (4)
O22	0.1254 (3)	0.61191 (14)	0.08990 (10)	0.0442 (4)
H22	0.171 (5)	0.6762 (19)	0.1175 (17)	0.057 (5)*
C23	0.3772 (3)	0.41108 (17)	0.34376 (13)	0.0326 (5)
H23	0.3968	0.3726	0.3804	0.039*
N24	0.4718 (3)	0.51521 (15)	0.36033 (11)	0.0330 (4)
O25	0.6014 (3)	0.56118 (14)	0.43349 (10)	0.0401 (4)
H25	0.660 (4)	0.6240 (19)	0.4383 (19)	0.057 (5)*
Cl26	0.73875 (8)	0.84868 (4)	0.53653 (3)	0.03528 (14)
O27	0.7932 (3)	0.78552 (13)	0.46270 (10)	0.0427 (4)
O28	0.5196 (3)	0.81507 (15)	0.52926 (11)	0.0499 (4)
O29	0.8271 (3)	0.82389 (17)	0.60343 (11)	0.0553 (5)
O30	0.8151 (3)	0.96563 (13)	0.54873 (10)	0.0434 (4)
Cl31	0.26813 (10)	0.90450 (5)	0.15095 (3)	0.04124 (15)
O32	0.2331 (3)	0.82404 (15)	0.19380 (11)	0.0560 (5)
O33	0.4797 (3)	0.96208 (19)	0.16471 (15)	0.0754 (7)
O34	0.1595 (4)	0.9815 (2)	0.18003 (17)	0.0863 (8)
O35	0.2001 (4)	0.84384 (18)	0.06653 (11)	0.0675 (6)
O36	−0.1866 (3)	0.39067 (13)	0.29253 (11)	0.0443 (4)
C37	−0.2187 (4)	0.32516 (19)	0.33066 (15)	0.0396 (5)
C38	−0.3576 (4)	0.20823 (19)	0.29095 (16)	0.0460 (6)
H38A	−0.4622	0.1921	0.3240	0.055*
H38B	−0.2784	0.1552	0.2856	0.055*
H38C	−0.4234	0.2007	0.2372	0.055*
C39	−0.1223 (4)	0.3578 (2)	0.41683 (17)	0.0549 (7)
H39A	−0.0541	0.3032	0.4229	0.066*
H39B	−0.2276	0.3593	0.4511	0.066*
H39C	−0.0219	0.4323	0.4331	0.066*
O40	0.4681 (3)	0.28523 (14)	0.10367 (11)	0.0483 (4)
C41	0.3870 (4)	0.2287 (2)	0.03438 (16)	0.0434 (6)
C42	0.3650 (5)	0.2801 (3)	−0.03011 (19)	0.0604 (7)
H42A	0.4182	0.2427	−0.0771	0.073*
H42B	0.4418	0.3601	−0.0092	0.073*
H42C	0.2204	0.2711	−0.0462	0.073*
C43	0.3012 (5)	0.1043 (2)	0.01018 (19)	0.0587 (7)
H43A	0.3174	0.0810	0.0577	0.070*
H43B	0.3738	0.0688	−0.0305	0.070*
H43C	0.1559	0.0815	−0.0126	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03140 (16)	0.02758 (15)	0.03222 (16)	0.00875 (11)	0.00584 (11)	0.00874 (11)
N2	0.0317 (9)	0.0327 (9)	0.0314 (9)	0.0095 (7)	0.0031 (7)	0.0115 (8)
C3	0.0349 (12)	0.0364 (11)	0.0337 (11)	0.0098 (9)	0.0034 (9)	0.0147 (10)
C4	0.0364 (12)	0.0390 (12)	0.0434 (13)	0.0054 (10)	0.0022 (10)	0.0173 (11)
C5	0.0418 (13)	0.0312 (11)	0.0447 (13)	0.0031 (10)	−0.0044 (10)	0.0138 (10)
C6	0.0438 (13)	0.0306 (11)	0.0388 (12)	0.0122 (10)	−0.0009 (10)	0.0090 (10)
C7	0.0356 (12)	0.0307 (11)	0.0335 (11)	0.0102 (9)	0.0017 (9)	0.0106 (9)
C8	0.0310 (11)	0.0401 (12)	0.0395 (12)	0.0108 (10)	0.0080 (9)	0.0145 (10)
N9	0.0359 (10)	0.0355 (10)	0.0387 (10)	0.0130 (8)	0.0083 (8)	0.0124 (8)
O10	0.0474 (11)	0.0384 (10)	0.0636 (12)	0.0130 (8)	0.0228 (9)	0.0068 (9)
C11	0.0370 (12)	0.0327 (11)	0.0337 (11)	0.0128 (9)	0.0054 (9)	0.0076 (9)
N12	0.0324 (10)	0.0312 (9)	0.0351 (10)	0.0096 (8)	0.0062 (8)	0.0103 (8)
O13	0.0389 (9)	0.0323 (8)	0.0553 (11)	0.0075 (7)	0.0174 (8)	0.0082 (8)
N14	0.0303 (9)	0.0301 (9)	0.0291 (9)	0.0104 (7)	0.0056 (7)	0.0086 (7)
C15	0.0339 (11)	0.0319 (11)	0.0303 (11)	0.0120 (9)	0.0060 (9)	0.0077 (9)
C16	0.0395 (13)	0.0337 (11)	0.0337 (11)	0.0105 (10)	0.0031 (9)	0.0065 (10)
C17	0.0434 (13)	0.0273 (11)	0.0396 (12)	0.0088 (9)	0.0058 (10)	0.0074 (9)
C18	0.0401 (13)	0.0304 (11)	0.0378 (12)	0.0123 (9)	0.0069 (10)	0.0112 (9)
C19	0.0324 (11)	0.0312 (10)	0.0325 (11)	0.0118 (9)	0.0081 (9)	0.0110 (9)
C20	0.0362 (12)	0.0333 (11)	0.0305 (11)	0.0108 (9)	0.0022 (9)	0.0071 (9)
N21	0.0365 (10)	0.0342 (10)	0.0322 (9)	0.0121 (8)	0.0053 (8)	0.0133 (8)
O22	0.0586 (11)	0.0336 (9)	0.0403 (9)	0.0119 (8)	0.0008 (8)	0.0161 (8)
C23	0.0346 (11)	0.0312 (11)	0.0333 (11)	0.0111 (9)	0.0048 (9)	0.0115 (9)
N24	0.0335 (10)	0.0337 (9)	0.0302 (9)	0.0107 (8)	0.0033 (7)	0.0084 (8)
O25	0.0409 (9)	0.0344 (9)	0.0370 (9)	0.0039 (7)	−0.0036 (7)	0.0093 (7)
Cl26	0.0376 (3)	0.0335 (3)	0.0326 (3)	0.0084 (2)	0.0057 (2)	0.0101 (2)
O27	0.0505 (10)	0.0370 (8)	0.0388 (9)	0.0128 (7)	0.0135 (8)	0.0087 (7)
O28	0.0372 (9)	0.0510 (10)	0.0548 (11)	0.0057 (8)	0.0122 (8)	0.0133 (9)
O29	0.0674 (13)	0.0616 (12)	0.0431 (10)	0.0213 (10)	0.0047 (9)	0.0261 (9)
O30	0.0444 (10)	0.0317 (8)	0.0490 (10)	0.0076 (7)	0.0066 (8)	0.0095 (7)
Cl31	0.0530 (4)	0.0328 (3)	0.0384 (3)	0.0139 (2)	0.0059 (3)	0.0121 (2)
O32	0.0862 (15)	0.0393 (9)	0.0420 (10)	0.0162 (9)	0.0009 (9)	0.0175 (8)
O33	0.0602 (14)	0.0625 (13)	0.0756 (15)	−0.0040 (11)	0.0070 (11)	0.0037 (12)
O34	0.112 (2)	0.0753 (15)	0.111 (2)	0.0657 (15)	0.0525 (17)	0.0474 (15)
O35	0.0881 (16)	0.0613 (12)	0.0377 (10)	0.0026 (11)	−0.0075 (10)	0.0166 (9)
O36	0.0444 (10)	0.0344 (8)	0.0526 (10)	0.0104 (7)	0.0159 (8)	0.0116 (8)
C37	0.0367 (13)	0.0340 (12)	0.0480 (13)	0.0127 (10)	0.0144 (10)	0.0099 (11)
C38	0.0495 (15)	0.0326 (12)	0.0514 (15)	0.0072 (11)	0.0120 (12)	0.0111 (11)
C39	0.0512 (16)	0.0511 (15)	0.0550 (16)	0.0111 (13)	0.0049 (13)	0.0118 (13)
O40	0.0512 (11)	0.0421 (10)	0.0482 (11)	0.0141 (8)	0.0086 (8)	0.0102 (9)
C41	0.0413 (14)	0.0423 (13)	0.0492 (15)	0.0155 (11)	0.0155 (11)	0.0146 (12)
C42	0.0649 (19)	0.0641 (18)	0.0596 (18)	0.0236 (15)	0.0125 (15)	0.0271 (15)
C43	0.069 (2)	0.0401 (14)	0.0580 (17)	0.0098 (13)	0.0167 (15)	0.0073 (13)

Geometric parameters (Å, º) top

Cu1—N2	1.9266 (18)	C19—C23	1.463 (3)
Cu1—N14	1.9698 (17)	C20—N21	1.271 (3)
Cu1—N9	2.1600 (19)	C20—H20	0.9500
Cu1—N12	2.1621 (18)	N21—O22	1.388 (2)
Cu1—N24	2.3271 (18)	O22—H22	0.80 (2)
Cu1—N21	2.3331 (18)	C23—N24	1.279 (3)
N2—C7	1.343 (3)	C23—H23	0.9500
N2—C3	1.345 (3)	N24—O25	1.373 (2)
C3—C4	1.385 (3)	O25—H25	0.79 (2)
C3—C8	1.462 (3)	Cl26—O30	1.4255 (16)
C4—C5	1.388 (4)	Cl26—O29	1.4411 (18)
C4—H4	0.9500	Cl26—O28	1.4418 (18)
C5—C6	1.379 (3)	Cl26—O27	1.4538 (16)
C5—H5	0.9500	Cl31—O34	1.413 (2)
C6—C7	1.388 (3)	Cl31—O33	1.418 (2)
C6—H6	0.9500	Cl31—O35	1.430 (2)
C7—C11	1.464 (3)	Cl31—O32	1.4505 (18)
C8—N9	1.282 (3)	O36—C37	1.225 (3)
C8—H8	0.9500	C37—C39	1.491 (4)
N9—O10	1.374 (2)	C37—C38	1.495 (3)
O10—H10	0.79 (2)	C38—H38A	0.9800
C11—N12	1.282 (3)	C38—H38B	0.9800
C11—H11	0.9500	C38—H38C	0.9800
N12—O13	1.370 (2)	C39—H39A	0.9800
O13—H13	0.78 (2)	C39—H39B	0.9800
N14—C19	1.349 (3)	C39—H39C	0.9800
N14—C15	1.354 (3)	O40—C41	1.217 (3)
C15—C16	1.384 (3)	C41—C43	1.492 (3)
C15—C20	1.462 (3)	C41—C42	1.497 (4)
C16—C17	1.387 (3)	C42—H42A	0.9800
C16—H16	0.9500	C42—H42B	0.9800
C17—C18	1.383 (3)	C42—H42C	0.9800
C17—H17	0.9500	C43—H43A	0.9800
C18—C19	1.387 (3)	C43—H43B	0.9800
C18—H18	0.9500	C43—H43C	0.9800

N2—Cu1—N14	178.59 (7)	C19—C18—H18	120.5
N2—Cu1—N9	77.78 (7)	N14—C19—C18	121.5 (2)
N14—Cu1—N9	100.85 (7)	N14—C19—C23	116.11 (18)
N2—Cu1—N12	77.68 (7)	C18—C19—C23	122.38 (19)
N14—Cu1—N12	103.70 (7)	N21—C20—C15	117.4 (2)
N9—Cu1—N12	155.42 (7)	N21—C20—H20	121.3
N2—Cu1—N24	103.94 (7)	C15—C20—H20	121.3
N14—Cu1—N24	75.81 (7)	C20—N21—O22	112.66 (18)
N9—Cu1—N24	95.39 (7)	C20—N21—Cu1	110.49 (14)
N12—Cu1—N24	91.76 (7)	O22—N21—Cu1	136.75 (13)
N2—Cu1—N21	104.80 (7)	N21—O22—H22	107 (2)
N14—Cu1—N21	75.43 (7)	N24—C23—C19	117.74 (19)
N9—Cu1—N21	89.67 (7)	N24—C23—H23	121.1
N12—Cu1—N21	95.29 (7)	C19—C23—H23	121.1
N24—Cu1—N21	151.24 (6)	C23—N24—O25	113.20 (18)
C7—N2—C3	120.56 (19)	C23—N24—Cu1	109.82 (14)
C7—N2—Cu1	119.70 (15)	O25—N24—Cu1	136.77 (13)
C3—N2—Cu1	119.73 (15)	N24—O25—H25	108 (2)
N2—C3—C4	121.3 (2)	O30—Cl26—O29	109.97 (11)
N2—C3—C8	113.45 (19)	O30—Cl26—O28	110.12 (11)
C4—C3—C8	125.3 (2)	O29—Cl26—O28	109.61 (12)
C3—C4—C5	118.1 (2)	O30—Cl26—O27	109.57 (10)
C3—C4—H4	121.0	O29—Cl26—O27	108.66 (11)
C5—C4—H4	121.0	O28—Cl26—O27	108.88 (11)
C6—C5—C4	120.5 (2)	O34—Cl31—O33	109.84 (16)
C6—C5—H5	119.7	O34—Cl31—O35	111.64 (16)
C4—C5—H5	119.7	O33—Cl31—O35	109.34 (14)
C5—C6—C7	118.5 (2)	O34—Cl31—O32	108.61 (13)
C5—C6—H6	120.7	O33—Cl31—O32	109.53 (14)
C7—C6—H6	120.7	O35—Cl31—O32	107.83 (12)
N2—C7—C6	121.0 (2)	O36—C37—C39	122.1 (2)
N2—C7—C11	113.83 (19)	O36—C37—C38	120.1 (2)
C6—C7—C11	125.2 (2)	C39—C37—C38	117.8 (2)
N9—C8—C3	116.6 (2)	C37—C38—H38A	109.5
N9—C8—H8	121.7	C37—C38—H38B	109.5
C3—C8—H8	121.7	H38A—C38—H38B	109.5
C8—N9—O10	113.17 (18)	C37—C38—H38C	109.5
C8—N9—Cu1	112.45 (15)	H38A—C38—H38C	109.5
O10—N9—Cu1	134.34 (14)	H38B—C38—H38C	109.5
N9—O10—H10	109 (2)	C37—C39—H39A	109.5
N12—C11—C7	116.09 (19)	C37—C39—H39B	109.5
N12—C11—H11	122.0	H39A—C39—H39B	109.5
C7—C11—H11	122.0	C37—C39—H39C	109.5
C11—N12—O13	113.45 (17)	H39A—C39—H39C	109.5
C11—N12—Cu1	112.69 (15)	H39B—C39—H39C	109.5
O13—N12—Cu1	133.84 (13)	O40—C41—C43	121.1 (2)
N12—O13—H13	108 (2)	O40—C41—C42	122.0 (2)
C19—N14—C15	119.35 (18)	C43—C41—C42	116.8 (2)
C19—N14—Cu1	120.27 (14)	C41—C42—H42A	109.5
C15—N14—Cu1	120.37 (14)	C41—C42—H42B	109.5
N14—C15—C16	121.6 (2)	H42A—C42—H42B	109.5
N14—C15—C20	116.27 (19)	C41—C42—H42C	109.5
C16—C15—C20	122.1 (2)	H42A—C42—H42C	109.5
C15—C16—C17	118.9 (2)	H42B—C42—H42C	109.5
C15—C16—H16	120.5	C41—C43—H43A	109.5
C17—C16—H16	120.5	C41—C43—H43B	109.5
C18—C17—C16	119.6 (2)	H43A—C43—H43B	109.5
C18—C17—H17	120.2	C41—C43—H43C	109.5
C16—C17—H17	120.2	H43A—C43—H43C	109.5
C17—C18—C19	119.0 (2)	H43B—C43—H43C	109.5
C17—C18—H18	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.79 (2)	1.89 (2)	2.655 (3)	162 (3)
O13—H13···O36	0.78 (2)	1.87 (2)	2.642 (2)	168 (3)
O22—H22···O32	0.80 (2)	1.91 (2)	2.700 (3)	168 (3)
O22—H22···O35	0.80 (2)	2.58 (3)	3.102 (3)	125 (3)
O25—H25···O27	0.79 (2)	1.97 (2)	2.756 (2)	173 (3)

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh68100) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.649 Mg m⁻³
a = 6.8625 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0680 (3) Å	Cell parameters from 25612 reflections
c = 17.5693 (5) Å	θ = 3.1–27.5°
α = 107.2708 (17)°	µ = 1.03 mm⁻¹
β = 94.0866 (13)°	T = 100 K
γ = 105.7498 (12)°	Rectangular prism, green
V = 1428.16 (7) Å³	0.26 × 0.23 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer	6476 independent reflections
Radiation source: fine-focus sealed tube	5285 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
/w and /f scans	h = −8→8
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38	k = −16→16
T_min = 0.776, T_max = 0.853	l = −22→22
25612 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0568P)² + 0.4415P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
6476 reflections	Δρ_max = 0.45 e Å⁻³
407 parameters	Δρ_min = −0.73 e Å⁻³
4 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (15)

Special details top

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

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

	x	y	z	U_iso*/U_eq
Cu1	0.35663 (4)	0.58026 (2)	0.260268 (15)	0.02533 (11)
N2	0.5096 (3)	0.73809 (15)	0.29648 (10)	0.0257 (4)
C3	0.6912 (3)	0.77214 (18)	0.27247 (13)	0.0278 (4)
C4	0.8082 (4)	0.88466 (19)	0.29920 (14)	0.0315 (5)
H4	0.9363	0.9082	0.2822	0.038*
C5	0.7335 (4)	0.96177 (19)	0.35135 (14)	0.0323 (5)
H5	0.8119	1.0392	0.3710	0.039*
C6	0.5447 (4)	0.92679 (18)	0.37513 (13)	0.0305 (5)
H6	0.4914	0.9795	0.4101	0.037*
C7	0.4360 (3)	0.81275 (18)	0.34642 (13)	0.0272 (4)
C8	0.7457 (3)	0.67991 (18)	0.21706 (13)	0.0293 (5)
H8	0.8688	0.6927	0.1949	0.035*
N9	0.6190 (3)	0.58106 (15)	0.20005 (11)	0.0300 (4)
O10	0.6770 (3)	0.49960 (14)	0.14556 (11)	0.0392 (4)
H10	0.597 (4)	0.442 (2)	0.1386 (18)	0.047 (4)*
C11	0.2374 (3)	0.76220 (18)	0.36671 (13)	0.0288 (5)
H11	0.1686	0.8061	0.4013	0.035*
N12	0.1618 (3)	0.65467 (15)	0.33476 (11)	0.0273 (4)
O13	−0.0225 (3)	0.61153 (14)	0.35671 (11)	0.0350 (4)
H13	−0.056 (5)	0.5477 (18)	0.3376 (18)	0.047 (4)*
N14	0.2053 (3)	0.41782 (14)	0.22236 (10)	0.0251 (4)
C15	0.0749 (3)	0.37009 (18)	0.15133 (12)	0.0264 (4)
C16	−0.0341 (3)	0.25609 (18)	0.12321 (13)	0.0290 (5)
H16	−0.1278	0.2243	0.0737	0.035*
C17	−0.0039 (4)	0.18967 (18)	0.16846 (14)	0.0306 (5)
H17	−0.0759	0.1113	0.1500	0.037*
C18	0.1319 (3)	0.23794 (17)	0.24098 (13)	0.0284 (5)
H18	0.1561	0.1931	0.2722	0.034*
C19	0.2324 (3)	0.35341 (17)	0.26714 (13)	0.0264 (4)
C20	0.0557 (3)	0.44456 (18)	0.10555 (13)	0.0284 (5)
H20	−0.0285	0.4165	0.0540	0.034*
N21	0.1564 (3)	0.54886 (15)	0.13744 (11)	0.0274 (4)
O22	0.1283 (3)	0.61196 (14)	0.08880 (10)	0.0349 (4)
H22	0.174 (5)	0.6747 (19)	0.1174 (17)	0.047 (4)*
C23	0.3725 (3)	0.41146 (17)	0.34437 (13)	0.0272 (4)
H23	0.3907	0.3730	0.3812	0.033*
N24	0.4697 (3)	0.51614 (15)	0.36028 (10)	0.0268 (4)
O25	0.6003 (2)	0.56217 (13)	0.43320 (9)	0.0318 (4)
H25	0.656 (4)	0.6254 (19)	0.4352 (18)	0.047 (4)*
Cl26	0.73509 (8)	0.84916 (4)	0.53464 (3)	0.02790 (13)
O27	0.7929 (3)	0.78733 (13)	0.46082 (9)	0.0332 (4)
O28	0.5140 (2)	0.81472 (14)	0.52660 (10)	0.0360 (4)
O29	0.8198 (3)	0.82189 (15)	0.60108 (10)	0.0390 (4)
O30	0.8142 (2)	0.96729 (12)	0.54852 (10)	0.0328 (4)
Cl31	0.27712 (9)	0.90565 (4)	0.14989 (3)	0.03166 (14)
O32	0.2388 (3)	0.82494 (14)	0.19354 (10)	0.0414 (4)
O33	0.4920 (3)	0.96221 (16)	0.16291 (12)	0.0512 (5)
O34	0.1690 (3)	0.98430 (16)	0.17871 (13)	0.0555 (5)
O35	0.2054 (3)	0.84370 (16)	0.06513 (10)	0.0486 (5)
O36	−0.1940 (2)	0.39171 (13)	0.29160 (10)	0.0335 (4)
C37	−0.2256 (3)	0.32576 (18)	0.32980 (14)	0.0311 (5)
C38	−0.3688 (4)	0.20861 (19)	0.29110 (15)	0.0353 (5)
H38A	−0.4748	0.1940	0.3244	0.042*
H38B	−0.2917	0.1545	0.2863	0.042*
H38C	−0.4336	0.2006	0.2372	0.042*
C39	−0.1244 (4)	0.3579 (2)	0.41562 (15)	0.0404 (6)
H39A	−0.0551	0.3031	0.4203	0.048*
H39B	−0.2285	0.3586	0.4510	0.048*
H39C	−0.0236	0.4330	0.4316	0.048*
O40	0.4625 (3)	0.28378 (13)	0.10387 (10)	0.0373 (4)
C41	0.3796 (4)	0.2277 (2)	0.03463 (14)	0.0334 (5)
C42	0.3606 (4)	0.2797 (2)	−0.02956 (17)	0.0444 (6)
H42A	0.4078	0.2396	−0.0776	0.053*
H42B	0.4448	0.3590	−0.0096	0.053*
H42C	0.2167	0.2746	−0.0436	0.053*
C43	0.2892 (4)	0.1025 (2)	0.01011 (16)	0.0421 (6)
H43A	0.2960	0.0789	0.0580	0.050*
H43B	0.3667	0.0663	−0.0283	0.050*
H43C	0.1456	0.0802	−0.0154	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02646 (16)	0.02183 (15)	0.02593 (16)	0.00694 (11)	0.00459 (11)	0.00567 (11)
N2	0.0265 (9)	0.0267 (9)	0.0244 (9)	0.0088 (7)	0.0020 (7)	0.0092 (7)
C3	0.0275 (11)	0.0281 (11)	0.0274 (10)	0.0072 (9)	0.0021 (9)	0.0102 (9)
C4	0.0294 (12)	0.0307 (11)	0.0335 (12)	0.0061 (9)	0.0033 (9)	0.0125 (9)
C5	0.0341 (12)	0.0248 (10)	0.0345 (12)	0.0036 (9)	−0.0021 (9)	0.0114 (9)
C6	0.0345 (12)	0.0247 (10)	0.0298 (11)	0.0094 (9)	0.0004 (9)	0.0062 (9)
C7	0.0298 (11)	0.0250 (10)	0.0262 (10)	0.0095 (9)	0.0016 (9)	0.0075 (9)
C8	0.0279 (11)	0.0317 (11)	0.0296 (11)	0.0102 (9)	0.0068 (9)	0.0105 (9)
N9	0.0304 (10)	0.0286 (9)	0.0306 (10)	0.0109 (8)	0.0059 (8)	0.0075 (8)
O10	0.0376 (10)	0.0281 (8)	0.0464 (10)	0.0091 (7)	0.0150 (8)	0.0037 (8)
C11	0.0311 (12)	0.0260 (10)	0.0281 (11)	0.0110 (9)	0.0046 (9)	0.0050 (9)
N12	0.0274 (9)	0.0253 (9)	0.0284 (9)	0.0076 (7)	0.0053 (7)	0.0079 (7)
O13	0.0301 (9)	0.0266 (8)	0.0439 (10)	0.0056 (7)	0.0126 (7)	0.0069 (7)
N14	0.0264 (9)	0.0257 (9)	0.0241 (9)	0.0104 (7)	0.0058 (7)	0.0068 (7)
C15	0.0261 (11)	0.0271 (10)	0.0246 (10)	0.0085 (9)	0.0052 (8)	0.0060 (9)
C16	0.0303 (11)	0.0275 (10)	0.0257 (10)	0.0092 (9)	0.0027 (9)	0.0039 (9)
C17	0.0338 (12)	0.0222 (10)	0.0320 (11)	0.0077 (9)	0.0074 (9)	0.0037 (9)
C18	0.0319 (12)	0.0241 (10)	0.0288 (11)	0.0096 (9)	0.0059 (9)	0.0072 (9)
C19	0.0268 (11)	0.0254 (10)	0.0265 (10)	0.0096 (8)	0.0061 (8)	0.0063 (8)
C20	0.0288 (11)	0.0292 (11)	0.0260 (10)	0.0094 (9)	0.0028 (9)	0.0073 (9)
N21	0.0312 (10)	0.0268 (9)	0.0262 (9)	0.0105 (8)	0.0052 (7)	0.0099 (7)
O22	0.0467 (10)	0.0263 (8)	0.0305 (8)	0.0096 (7)	0.0014 (7)	0.0102 (7)
C23	0.0288 (11)	0.0252 (10)	0.0277 (11)	0.0087 (9)	0.0047 (9)	0.0086 (9)
N24	0.0280 (9)	0.0262 (9)	0.0241 (9)	0.0083 (7)	0.0027 (7)	0.0059 (7)
O25	0.0337 (9)	0.0273 (8)	0.0280 (8)	0.0039 (7)	−0.0021 (7)	0.0065 (7)
Cl26	0.0301 (3)	0.0256 (3)	0.0260 (3)	0.0073 (2)	0.0040 (2)	0.0068 (2)
O27	0.0398 (9)	0.0282 (8)	0.0286 (8)	0.0098 (7)	0.0095 (7)	0.0048 (6)
O28	0.0286 (8)	0.0365 (9)	0.0378 (9)	0.0052 (7)	0.0071 (7)	0.0088 (7)
O29	0.0463 (10)	0.0428 (9)	0.0318 (9)	0.0148 (8)	0.0036 (7)	0.0175 (8)
O30	0.0356 (9)	0.0244 (8)	0.0349 (8)	0.0069 (7)	0.0049 (7)	0.0068 (7)
Cl31	0.0391 (3)	0.0259 (3)	0.0294 (3)	0.0105 (2)	0.0046 (2)	0.0079 (2)
O32	0.0606 (12)	0.0294 (8)	0.0328 (9)	0.0108 (8)	0.0033 (8)	0.0118 (7)
O33	0.0415 (11)	0.0423 (10)	0.0516 (11)	0.0007 (8)	0.0068 (9)	0.0007 (9)
O34	0.0696 (14)	0.0480 (11)	0.0692 (13)	0.0376 (10)	0.0287 (11)	0.0268 (10)
O35	0.0634 (13)	0.0440 (10)	0.0293 (9)	0.0054 (9)	−0.0034 (8)	0.0116 (8)
O36	0.0347 (9)	0.0265 (8)	0.0388 (9)	0.0094 (7)	0.0115 (7)	0.0087 (7)
C37	0.0286 (12)	0.0263 (11)	0.0370 (12)	0.0110 (9)	0.0104 (9)	0.0050 (10)
C38	0.0351 (13)	0.0278 (11)	0.0382 (13)	0.0057 (10)	0.0079 (10)	0.0071 (10)
C39	0.0398 (14)	0.0359 (13)	0.0401 (13)	0.0078 (11)	0.0052 (11)	0.0086 (11)
O40	0.0391 (10)	0.0330 (9)	0.0353 (9)	0.0104 (7)	0.0054 (7)	0.0058 (7)
C41	0.0322 (12)	0.0317 (12)	0.0374 (13)	0.0112 (10)	0.0105 (10)	0.0108 (10)
C42	0.0473 (16)	0.0432 (14)	0.0450 (14)	0.0145 (12)	0.0094 (12)	0.0167 (12)
C43	0.0510 (16)	0.0309 (12)	0.0397 (13)	0.0090 (11)	0.0120 (12)	0.0073 (11)

Geometric parameters (Å, º) top

Cu1—N2	1.9263 (18)	C19—C23	1.466 (3)
Cu1—N14	1.9732 (17)	C20—N21	1.276 (3)
Cu1—N9	2.1514 (19)	C20—H20	0.9500
Cu1—N12	2.1553 (18)	N21—O22	1.389 (2)
Cu1—N24	2.3291 (18)	O22—H22	0.78 (2)
Cu1—N21	2.3364 (18)	C23—N24	1.283 (3)
N2—C7	1.341 (3)	C23—H23	0.9500
N2—C3	1.347 (3)	N24—O25	1.376 (2)
C3—C4	1.386 (3)	O25—H25	0.80 (2)
C3—C8	1.463 (3)	Cl26—O30	1.4284 (16)
C4—C5	1.384 (3)	Cl26—O28	1.4438 (17)
C4—H4	0.9500	Cl26—O29	1.4459 (17)
C5—C6	1.390 (3)	Cl26—O27	1.4550 (16)
C5—H5	0.9500	Cl31—O34	1.4218 (19)
C6—C7	1.389 (3)	Cl31—O33	1.4257 (19)
C6—H6	0.9500	Cl31—O35	1.4417 (18)
C7—C11	1.464 (3)	Cl31—O32	1.4588 (17)
C8—N9	1.280 (3)	O36—C37	1.226 (3)
C8—H8	0.9500	C37—C38	1.497 (3)
N9—O10	1.374 (2)	C37—C39	1.499 (3)
O10—H10	0.77 (2)	C38—H38A	0.9800
C11—N12	1.286 (3)	C38—H38B	0.9800
C11—H11	0.9500	C38—H38C	0.9800
N12—O13	1.370 (2)	C39—H39A	0.9800
O13—H13	0.76 (2)	C39—H39B	0.9800
N14—C19	1.349 (3)	C39—H39C	0.9800
N14—C15	1.350 (3)	O40—C41	1.219 (3)
C15—C16	1.389 (3)	C41—C42	1.495 (4)
C15—C20	1.460 (3)	C41—C43	1.497 (3)
C16—C17	1.383 (3)	C42—H42A	0.9800
C16—H16	0.9500	C42—H42B	0.9800
C17—C18	1.387 (3)	C42—H42C	0.9800
C17—H17	0.9500	C43—H43A	0.9800
C18—C19	1.393 (3)	C43—H43B	0.9800
C18—H18	0.9500	C43—H43C	0.9800

N2—Cu1—N14	178.75 (7)	C19—C18—H18	120.6
N2—Cu1—N9	77.87 (7)	N14—C19—C18	121.5 (2)
N14—Cu1—N9	100.92 (7)	N14—C19—C23	116.40 (18)
N2—Cu1—N12	77.71 (7)	C18—C19—C23	122.12 (19)
N14—Cu1—N12	103.51 (7)	N21—C20—C15	117.48 (19)
N9—Cu1—N12	155.52 (7)	N21—C20—H20	121.3
N2—Cu1—N24	103.87 (7)	C15—C20—H20	121.3
N14—Cu1—N24	75.87 (7)	C20—N21—O22	112.80 (18)
N9—Cu1—N24	95.71 (7)	C20—N21—Cu1	110.20 (14)
N12—Cu1—N24	91.69 (7)	O22—N21—Cu1	136.87 (13)
N2—Cu1—N21	104.84 (7)	N21—O22—H22	104 (2)
N14—Cu1—N21	75.40 (7)	N24—C23—C19	117.44 (19)
N9—Cu1—N21	89.31 (7)	N24—C23—H23	121.3
N12—Cu1—N21	95.33 (7)	C19—C23—H23	121.3
N24—Cu1—N21	151.27 (6)	C23—N24—O25	112.95 (17)
C7—N2—C3	120.65 (18)	C23—N24—Cu1	109.90 (14)
C7—N2—Cu1	119.71 (15)	O25—N24—Cu1	136.96 (13)
C3—N2—Cu1	119.62 (15)	N24—O25—H25	104 (2)
N2—C3—C4	121.2 (2)	O30—Cl26—O28	110.50 (10)
N2—C3—C8	113.26 (19)	O30—Cl26—O29	109.97 (10)
C4—C3—C8	125.6 (2)	O28—Cl26—O29	109.28 (10)
C5—C4—C3	118.3 (2)	O30—Cl26—O27	109.65 (9)
C5—C4—H4	120.8	O28—Cl26—O27	108.95 (10)
C3—C4—H4	120.8	O29—Cl26—O27	108.45 (10)
C4—C5—C6	120.5 (2)	O34—Cl31—O33	110.29 (12)
C4—C5—H5	119.8	O34—Cl31—O35	110.91 (13)
C6—C5—H5	119.8	O33—Cl31—O35	109.79 (12)
C7—C6—C5	118.2 (2)	O34—Cl31—O32	108.69 (11)
C7—C6—H6	120.9	O33—Cl31—O32	109.38 (12)
C5—C6—H6	120.9	O35—Cl31—O32	107.73 (10)
N2—C7—C6	121.2 (2)	O36—C37—C38	120.2 (2)
N2—C7—C11	113.86 (18)	O36—C37—C39	122.2 (2)
C6—C7—C11	125.0 (2)	C38—C37—C39	117.6 (2)
N9—C8—C3	116.55 (19)	C37—C38—H38A	109.5
N9—C8—H8	121.7	C37—C38—H38B	109.5
C3—C8—H8	121.7	H38A—C38—H38B	109.5
C8—N9—O10	113.14 (18)	C37—C38—H38C	109.5
C8—N9—Cu1	112.67 (15)	H38A—C38—H38C	109.5
O10—N9—Cu1	134.16 (14)	H38B—C38—H38C	109.5
N9—O10—H10	108 (2)	C37—C39—H39A	109.5
N12—C11—C7	115.81 (19)	C37—C39—H39B	109.5
N12—C11—H11	122.1	H39A—C39—H39B	109.5
C7—C11—H11	122.1	C37—C39—H39C	109.5
C11—N12—O13	113.42 (18)	H39A—C39—H39C	109.5
C11—N12—Cu1	112.90 (15)	H39B—C39—H39C	109.5
O13—N12—Cu1	133.67 (13)	O40—C41—C42	122.1 (2)
N12—O13—H13	108 (2)	O40—C41—C43	121.2 (2)
C19—N14—C15	119.46 (18)	C42—C41—C43	116.7 (2)
C19—N14—Cu1	120.14 (14)	C41—C42—H42A	109.5
C15—N14—Cu1	120.41 (14)	C41—C42—H42B	109.5
N14—C15—C16	121.7 (2)	H42A—C42—H42B	109.5
N14—C15—C20	116.43 (18)	C41—C42—H42C	109.5
C16—C15—C20	121.87 (19)	H42A—C42—H42C	109.5
C17—C16—C15	118.9 (2)	H42B—C42—H42C	109.5
C17—C16—H16	120.6	C41—C43—H43A	109.5
C15—C16—H16	120.6	C41—C43—H43B	109.5
C16—C17—C18	119.7 (2)	H43A—C43—H43B	109.5
C16—C17—H17	120.2	C41—C43—H43C	109.5
C18—C17—H17	120.2	H43A—C43—H43C	109.5
C17—C18—C19	118.8 (2)	H43B—C43—H43C	109.5
C17—C18—H18	120.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.77 (2)	1.91 (2)	2.650 (2)	162 (3)
O13—H13···O36	0.76 (2)	1.89 (2)	2.640 (2)	168 (3)
O22—H22···O32	0.78 (2)	1.93 (2)	2.706 (2)	170 (3)
O22—H22···O35	0.78 (2)	2.60 (3)	3.088 (2)	122 (3)
O25—H25···O27	0.80 (2)	1.96 (2)	2.755 (2)	170 (3)

Bis[2,6-bis{oximomethyl}pyridine]copper(II) diperchlorate bis-acetone solvate (mh6830) top

Crystal data top

C₁₄H₁₄CuN₆O₄·2[ClO₄]·2[C₃H₆O]	Z = 2
M_r = 708.91	F(000) = 726
Triclinic, P1	D_x = 1.650 Mg m⁻³
a = 6.8472 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0645 (5) Å	Cell parameters from 11317 reflections
c = 17.5942 (6) Å	θ = 3.3–27.6°
α = 107.211 (2)°	µ = 1.03 mm⁻¹
β = 93.712 (2)°	T = 30 K
γ = 105.976 (2)°	Rectangular prism, green
V = 1426.92 (8) Å³	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker X8 Apex diffractometer	6087 independent reflections
Radiation source: rotating anode	5373 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 120 microns pixels mm^-1	θ_max = 27.6°, θ_min = 3.3°
/w and /f scans	h = −8→8
Absorption correction: multi-scan Sheldrick, G. M. (2002). SADABS v. 2.03. University of G/ottingen, Germany.	k = −16→16
T_min = 0.822, T_max = 1.154	l = −22→22
11317 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0306P)² + 1.0526P] where P = (F_o² + 2F_c²)/3
6089 reflections	(Δ/σ)_max = 0.001
406 parameters	Δρ_max = 0.47 e Å⁻³
4 restraints	Δρ_min = −0.63 e Å⁻³

Special details top

Experimental. Rotating anode power 3 kW.

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

	x	y	z	U_iso*/U_eq
Cu1	0.35668 (3)	0.580458 (16)	0.259984 (11)	0.00772 (6)
N2	0.5121 (2)	0.73926 (11)	0.29580 (8)	0.0086 (3)
C3	0.6940 (3)	0.77259 (14)	0.27155 (9)	0.0104 (3)
C4	0.8135 (3)	0.88532 (14)	0.29751 (10)	0.0114 (3)
H4	0.9419	0.9084	0.2801	0.014*
C5	0.7383 (3)	0.96349 (14)	0.35012 (10)	0.0116 (3)
H5	0.8171	1.0409	0.3693	0.014*
C6	0.5494 (3)	0.92865 (14)	0.37447 (10)	0.0107 (3)
H6	0.4968	0.9816	0.4096	0.013*
C7	0.4382 (3)	0.81391 (14)	0.34607 (9)	0.0098 (3)
C8	0.7489 (3)	0.67981 (14)	0.21580 (10)	0.0108 (3)
H8	0.8721	0.6925	0.1933	0.013*
N9	0.6203 (2)	0.58045 (12)	0.19930 (8)	0.0108 (3)
O10	0.6767 (2)	0.49813 (10)	0.14440 (7)	0.0144 (2)
H10	0.594 (4)	0.4389 (19)	0.1404 (15)	0.026 (3)*
C11	0.2379 (3)	0.76341 (14)	0.36654 (9)	0.0100 (3)
H11	0.1690	0.8073	0.4012	0.012*
N12	0.1612 (2)	0.65532 (12)	0.33439 (8)	0.0102 (3)
O13	−0.02491 (19)	0.61178 (10)	0.35641 (8)	0.0136 (2)
H13	−0.062 (4)	0.5446 (18)	0.3332 (15)	0.026 (3)*
N14	0.2036 (2)	0.41762 (11)	0.22253 (8)	0.0081 (2)
C15	0.0723 (3)	0.36926 (14)	0.15163 (9)	0.0099 (3)
C16	−0.0387 (3)	0.25509 (14)	0.12381 (10)	0.0112 (3)
H16	−0.1323	0.2235	0.0746	0.013*
C17	−0.0102 (3)	0.18780 (14)	0.16961 (10)	0.0113 (3)
H17	−0.0822	0.1094	0.1514	0.014*
C18	0.1255 (3)	0.23730 (14)	0.24230 (10)	0.0110 (3)
H18	0.1479	0.1929	0.2741	0.013*
C19	0.2279 (2)	0.35282 (14)	0.26781 (9)	0.0093 (3)
C20	0.0548 (3)	0.44388 (14)	0.10498 (10)	0.0101 (3)
H20	−0.0287	0.4157	0.0535	0.012*
N21	0.1574 (2)	0.54876 (12)	0.13689 (8)	0.0106 (3)
O22	0.1309 (2)	0.61191 (11)	0.08812 (7)	0.0133 (2)
H22	0.180 (4)	0.6744 (19)	0.1172 (15)	0.026 (3)*
C23	0.3690 (3)	0.41179 (14)	0.34532 (10)	0.0103 (3)
H23	0.3856	0.3738	0.3825	0.012*
N24	0.4678 (2)	0.51576 (12)	0.36038 (8)	0.0101 (3)
O25	0.59941 (19)	0.56277 (10)	0.43334 (7)	0.0123 (2)
H25	0.652 (4)	0.6251 (18)	0.4360 (15)	0.026 (3)*
Cl26	0.73327 (6)	0.84941 (3)	0.53318 (2)	0.00900 (9)
O27	0.79322 (19)	0.78883 (10)	0.45889 (7)	0.0123 (2)
O28	0.51059 (19)	0.81485 (10)	0.52508 (7)	0.0137 (2)
O29	0.8168 (2)	0.82020 (11)	0.59919 (7)	0.0143 (2)
O30	0.81419 (19)	0.96892 (10)	0.54840 (7)	0.0127 (2)
Cl31	0.28283 (6)	0.90646 (3)	0.14951 (2)	0.00973 (9)
O32	0.2409 (2)	0.82523 (10)	0.19364 (7)	0.0145 (2)
O33	0.5008 (2)	0.96156 (11)	0.16205 (8)	0.0175 (3)
O34	0.1746 (2)	0.98699 (11)	0.17805 (8)	0.0179 (3)
O35	0.2097 (2)	0.84415 (11)	0.06436 (7)	0.0168 (3)
O36	−0.20036 (19)	0.39218 (10)	0.29049 (7)	0.0122 (2)
C37	−0.2308 (3)	0.32599 (14)	0.32883 (10)	0.0110 (3)
C38	−0.3781 (3)	0.20867 (14)	0.29120 (10)	0.0128 (3)
H38A	−0.4823	0.1949	0.3257	0.015*
H38B	−0.3025	0.1538	0.2854	0.015*
H38C	−0.4455	0.2009	0.2380	0.015*
C39	−0.1268 (3)	0.35842 (15)	0.41424 (10)	0.0153 (3)
H39A	−0.0548	0.3045	0.4182	0.018*
H39B	−0.2303	0.3578	0.4502	0.018*
H39C	−0.0276	0.4341	0.4299	0.018*
O40	0.45923 (19)	0.28220 (10)	0.10423 (7)	0.0138 (2)
C41	0.3752 (3)	0.22666 (14)	0.03469 (10)	0.0118 (3)
C42	0.3587 (3)	0.28026 (15)	−0.02973 (11)	0.0166 (3)
H42A	0.3999	0.2380	−0.0786	0.020*
H42B	0.4494	0.3583	−0.0105	0.020*
H42C	0.2163	0.2792	−0.0418	0.020*
C43	0.2809 (3)	0.10073 (14)	0.00994 (11)	0.0160 (3)
H43A	0.2780	0.0773	0.0580	0.019*
H43B	0.3632	0.0640	−0.0258	0.019*
H43C	0.1403	0.0790	−0.0184	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.00681 (10)	0.00617 (10)	0.00985 (10)	0.00171 (7)	0.00119 (7)	0.00244 (7)
N2	0.0079 (6)	0.0082 (6)	0.0103 (6)	0.0027 (5)	0.0002 (5)	0.0040 (5)
C3	0.0105 (8)	0.0117 (7)	0.0096 (7)	0.0038 (6)	−0.0004 (6)	0.0046 (6)
C4	0.0088 (7)	0.0127 (8)	0.0130 (7)	0.0016 (6)	0.0002 (6)	0.0065 (6)
C5	0.0126 (8)	0.0079 (7)	0.0133 (8)	0.0015 (6)	−0.0027 (6)	0.0046 (6)
C6	0.0115 (8)	0.0094 (7)	0.0108 (7)	0.0039 (6)	−0.0010 (6)	0.0026 (6)
C7	0.0106 (8)	0.0101 (7)	0.0093 (7)	0.0043 (6)	−0.0008 (6)	0.0035 (6)
C8	0.0090 (7)	0.0130 (8)	0.0117 (7)	0.0041 (6)	0.0008 (6)	0.0053 (6)
N9	0.0108 (7)	0.0117 (7)	0.0109 (6)	0.0058 (5)	0.0016 (5)	0.0030 (5)
O10	0.0131 (6)	0.0095 (6)	0.0192 (6)	0.0041 (5)	0.0064 (5)	0.0014 (5)
C11	0.0101 (7)	0.0096 (7)	0.0109 (7)	0.0036 (6)	0.0008 (6)	0.0036 (6)
N12	0.0075 (6)	0.0111 (6)	0.0121 (6)	0.0024 (5)	0.0012 (5)	0.0044 (5)
O13	0.0091 (6)	0.0096 (6)	0.0196 (6)	−0.0002 (5)	0.0052 (5)	0.0031 (5)
N14	0.0064 (6)	0.0091 (6)	0.0104 (6)	0.0041 (5)	0.0019 (5)	0.0037 (5)
C15	0.0086 (7)	0.0109 (7)	0.0110 (7)	0.0047 (6)	0.0019 (6)	0.0030 (6)
C16	0.0101 (7)	0.0114 (7)	0.0109 (7)	0.0035 (6)	0.0017 (6)	0.0017 (6)
C17	0.0113 (8)	0.0085 (7)	0.0134 (7)	0.0030 (6)	0.0036 (6)	0.0025 (6)
C18	0.0108 (7)	0.0106 (7)	0.0133 (7)	0.0048 (6)	0.0034 (6)	0.0049 (6)
C19	0.0072 (7)	0.0113 (7)	0.0113 (7)	0.0050 (6)	0.0029 (6)	0.0038 (6)
C20	0.0079 (7)	0.0124 (7)	0.0109 (7)	0.0038 (6)	0.0006 (6)	0.0044 (6)
N21	0.0103 (7)	0.0116 (6)	0.0126 (6)	0.0048 (5)	0.0027 (5)	0.0064 (5)
O22	0.0171 (6)	0.0091 (6)	0.0138 (6)	0.0030 (5)	−0.0001 (5)	0.0056 (5)
C23	0.0097 (7)	0.0112 (7)	0.0109 (7)	0.0045 (6)	0.0015 (6)	0.0037 (6)
N24	0.0086 (6)	0.0116 (6)	0.0097 (6)	0.0037 (5)	0.0001 (5)	0.0028 (5)
O25	0.0116 (6)	0.0107 (6)	0.0112 (5)	0.0004 (5)	−0.0029 (4)	0.0026 (4)
Cl26	0.00856 (18)	0.00856 (17)	0.00973 (17)	0.00231 (13)	0.00089 (13)	0.00318 (13)
O27	0.0139 (6)	0.0106 (5)	0.0122 (5)	0.0044 (5)	0.0036 (4)	0.0024 (4)
O28	0.0087 (6)	0.0143 (6)	0.0170 (6)	0.0020 (4)	0.0018 (5)	0.0051 (5)
O29	0.0148 (6)	0.0165 (6)	0.0131 (6)	0.0049 (5)	0.0002 (5)	0.0075 (5)
O30	0.0134 (6)	0.0087 (5)	0.0153 (6)	0.0028 (5)	0.0016 (5)	0.0035 (4)
Cl31	0.01092 (18)	0.00815 (17)	0.01041 (17)	0.00312 (13)	0.00116 (13)	0.00341 (13)
O32	0.0206 (7)	0.0108 (6)	0.0129 (6)	0.0042 (5)	0.0010 (5)	0.0059 (5)
O33	0.0126 (6)	0.0147 (6)	0.0204 (6)	0.0010 (5)	0.0023 (5)	0.0017 (5)
O34	0.0210 (7)	0.0159 (6)	0.0238 (7)	0.0126 (5)	0.0086 (5)	0.0094 (5)
O35	0.0213 (7)	0.0157 (6)	0.0108 (6)	0.0031 (5)	−0.0020 (5)	0.0040 (5)
O36	0.0108 (6)	0.0101 (5)	0.0170 (6)	0.0043 (4)	0.0041 (5)	0.0048 (5)
C37	0.0080 (7)	0.0096 (7)	0.0144 (8)	0.0034 (6)	0.0031 (6)	0.0015 (6)
C38	0.0123 (8)	0.0097 (7)	0.0151 (8)	0.0020 (6)	0.0018 (6)	0.0034 (6)
C39	0.0143 (8)	0.0148 (8)	0.0153 (8)	0.0029 (6)	0.0000 (6)	0.0047 (7)
O40	0.0133 (6)	0.0130 (6)	0.0138 (6)	0.0040 (5)	0.0014 (5)	0.0028 (5)
C41	0.0094 (7)	0.0125 (8)	0.0157 (8)	0.0055 (6)	0.0047 (6)	0.0052 (6)
C42	0.0184 (9)	0.0151 (8)	0.0176 (8)	0.0053 (7)	0.0022 (7)	0.0073 (7)
C43	0.0186 (9)	0.0111 (8)	0.0164 (8)	0.0027 (7)	0.0040 (7)	0.0030 (6)

Geometric parameters (Å, º) top

Cu1—N2	1.9386 (14)	C19—C23	1.478 (2)
Cu1—N14	1.9780 (14)	C20—N21	1.284 (2)
Cu1—N9	2.1559 (14)	C20—H20	0.9500
Cu1—N12	2.1567 (14)	N21—O22	1.3896 (18)
Cu1—N24	2.3403 (14)	O22—H22	0.79 (2)
Cu1—N21	2.3450 (14)	C23—N24	1.277 (2)
N2—C3	1.343 (2)	C23—H23	0.9500
N2—C7	1.345 (2)	N24—O25	1.3842 (18)
C3—C4	1.392 (2)	O25—H25	0.78 (2)
C3—C8	1.472 (2)	Cl26—O30	1.4401 (12)
C4—C5	1.398 (2)	Cl26—O28	1.4505 (13)
C4—H4	0.9500	Cl26—O29	1.4554 (12)
C5—C6	1.388 (3)	Cl26—O27	1.4627 (12)
C5—H5	0.9500	Cl31—O33	1.4373 (14)
C6—C7	1.398 (2)	Cl31—O34	1.4398 (13)
C6—H6	0.9500	Cl31—O35	1.4543 (12)
C7—C11	1.467 (2)	Cl31—O32	1.4697 (12)
C8—N9	1.288 (2)	O36—C37	1.229 (2)
C8—H8	0.9500	C37—C39	1.504 (2)
N9—O10	1.3786 (18)	C37—C38	1.506 (2)
O10—H10	0.80 (2)	C38—H38A	0.9800
C11—N12	1.293 (2)	C38—H38B	0.9800
C11—H11	0.9500	C38—H38C	0.9800
N12—O13	1.3759 (19)	C39—H39A	0.9800
O13—H13	0.81 (2)	C39—H39B	0.9800
N14—C19	1.356 (2)	C39—H39C	0.9800
N14—C15	1.356 (2)	O40—C41	1.228 (2)
C15—C16	1.392 (2)	C41—C43	1.506 (2)
C15—C20	1.471 (2)	C41—C42	1.511 (2)
C16—C17	1.398 (2)	C42—H42A	0.9800
C16—H16	0.9500	C42—H42B	0.9800
C17—C18	1.394 (2)	C42—H42C	0.9800
C17—H17	0.9500	C43—H43A	0.9800
C18—C19	1.395 (2)	C43—H43B	0.9800
C18—H18	0.9500	C43—H43C	0.9800

N2—Cu1—N14	178.71 (6)	C19—C18—H18	120.4
N2—Cu1—N9	77.94 (6)	N14—C19—C18	121.66 (15)
N14—Cu1—N9	100.80 (5)	N14—C19—C23	116.06 (14)
N2—Cu1—N12	77.77 (6)	C18—C19—C23	122.28 (14)
N14—Cu1—N12	103.49 (6)	N21—C20—C15	117.08 (14)
N9—Cu1—N12	155.65 (6)	N21—C20—H20	121.5
N2—Cu1—N24	104.00 (5)	C15—C20—H20	121.5
N14—Cu1—N24	75.77 (5)	C20—N21—O22	112.62 (13)
N9—Cu1—N24	95.84 (5)	C20—N21—Cu1	110.45 (11)
N12—Cu1—N24	91.63 (5)	O22—N21—Cu1	136.81 (10)
N2—Cu1—N21	104.84 (5)	N21—O22—H22	103.0 (19)
N14—Cu1—N21	75.38 (5)	N24—C23—C19	117.51 (14)
N9—Cu1—N21	89.06 (5)	N24—C23—H23	121.2
N12—Cu1—N21	95.50 (5)	C19—C23—H23	121.2
N24—Cu1—N21	151.15 (5)	C23—N24—O25	113.22 (13)
C3—N2—C7	121.11 (14)	C23—N24—Cu1	110.09 (11)
C3—N2—Cu1	119.48 (11)	O25—N24—Cu1	136.47 (10)
C7—N2—Cu1	119.40 (12)	N24—O25—H25	104.6 (19)
N2—C3—C4	121.45 (15)	O30—Cl26—O28	110.47 (7)
N2—C3—C8	113.61 (14)	O30—Cl26—O29	109.90 (7)
C4—C3—C8	124.93 (15)	O28—Cl26—O29	109.25 (8)
C3—C4—C5	117.85 (16)	O30—Cl26—O27	109.63 (7)
C3—C4—H4	121.1	O28—Cl26—O27	109.17 (7)
C5—C4—H4	121.1	O29—Cl26—O27	108.38 (7)
C6—C5—C4	120.43 (15)	O33—Cl31—O34	110.85 (8)
C6—C5—H5	119.8	O33—Cl31—O35	109.75 (8)
C4—C5—H5	119.8	O34—Cl31—O35	110.31 (8)
C5—C6—C7	118.50 (15)	O33—Cl31—O32	109.23 (8)
C5—C6—H6	120.7	O34—Cl31—O32	108.87 (8)
C7—C6—H6	120.7	O35—Cl31—O32	107.77 (7)
N2—C7—C6	120.64 (15)	O36—C37—C39	122.08 (15)
N2—C7—C11	114.07 (14)	O36—C37—C38	120.26 (15)
C6—C7—C11	125.29 (15)	C39—C37—C38	117.66 (14)
N9—C8—C3	116.24 (15)	C37—C38—H38A	109.5
N9—C8—H8	121.9	C37—C38—H38B	109.5
C3—C8—H8	121.9	H38A—C38—H38B	109.5
C8—N9—O10	113.32 (14)	C37—C38—H38C	109.5
C8—N9—Cu1	112.69 (11)	H38A—C38—H38C	109.5
O10—N9—Cu1	133.93 (11)	H38B—C38—H38C	109.5
N9—O10—H10	106.8 (19)	C37—C39—H39A	109.5
N12—C11—C7	115.68 (14)	C37—C39—H39B	109.5
N12—C11—H11	122.2	H39A—C39—H39B	109.5
C7—C11—H11	122.2	C37—C39—H39C	109.5
C11—N12—O13	113.48 (13)	H39A—C39—H39C	109.5
C11—N12—Cu1	113.06 (11)	H39B—C39—H39C	109.5
O13—N12—Cu1	133.43 (10)	O40—C41—C43	120.98 (15)
N12—O13—H13	107 (2)	O40—C41—C42	122.27 (15)
C19—N14—C15	119.06 (14)	C43—C41—C42	116.75 (15)
C19—N14—Cu1	120.27 (11)	C41—C42—H42A	109.5
C15—N14—Cu1	120.67 (11)	C41—C42—H42B	109.5
N14—C15—C16	122.10 (15)	H42A—C42—H42B	109.5
N14—C15—C20	116.33 (14)	C41—C42—H42C	109.5
C16—C15—C20	121.57 (15)	H42A—C42—H42C	109.5
C15—C16—C17	118.84 (15)	H42B—C42—H42C	109.5
C15—C16—H16	120.6	C41—C43—H43A	109.5
C17—C16—H16	120.6	C41—C43—H43B	109.5
C18—C17—C16	119.10 (15)	H43A—C43—H43B	109.5
C18—C17—H17	120.5	C41—C43—H43C	109.5
C16—C17—H17	120.5	H43A—C43—H43C	109.5
C17—C18—C19	119.21 (15)	H43B—C43—H43C	109.5
C17—C18—H18	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O40	0.80 (2)	1.89 (2)	2.6545 (18)	160 (3)
O13—H13···O36	0.81 (2)	1.85 (2)	2.6406 (17)	167 (3)
O22—H22···O32	0.79 (2)	1.94 (2)	2.7171 (18)	168 (3)
O22—H22···O35	0.79 (2)	2.61 (3)	3.0904 (18)	121 (2)
O25—H25···O27	0.78 (2)	1.99 (2)	2.7686 (18)	172 (3)

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