Crystal structure of a tetranuclear CuII complex with an O,N,N′-donor Schiff base ligand: hexa-μ2-acetato-bis­(2-{[(2,2,6,6-tetra­methyl­piperidin-4-yl)imino]­meth­yl}phenolato-κ3O,N,N′)tetra­copper(II)

Huang, G.; Liu, X.

doi:10.1107/S2056989016005041

Crystal structure of a tetranuclear Cu^II complex with an O,N,N′-donor Schiff base ligand: hexa-μ₂-acetato-bis(2-{[(2,2,6,6-tetramethylpiperidin-4-yl)imino]methyl}phenolato-κ³O,N,N′)tetracopper(II)

In the title compound, the symmetry-unique terminal Cu^II ion is O,N,N′-coordinated by a 2-{[(2,2,6,6-tetramethylpiperidin-4-yl)imino]methyl}phenolate ligand and an O atom from an acetate group in a slightly distorted tetrahedral coordination environment. The symmetry-unique central Cu^II ion is coordinated by a different O atom of the same acetate group and by four bridging acetate ligands, which connect the asymmetric unit into a dimeric complex and form a slightly distorted square-pyramidal coordination environment.

Keywords: crystal structure; Schiff base ligand; boat conformation; piperidines; copper(II) complex.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016005041/lh5808sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016005041/lh5808Isup2.hkl Contains datablock I

CCDC reference: 1470356

checkCIF report

Key indicators

Single-crystal X-ray study
T = 250 K
Mean (C-C) = 0.005 Å
R factor = 0.038
wR factor = 0.109
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.975 Note
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         48 Ang3

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14 Do !
            CU2 -CU2 -O3  -C17  -131.20  0.80   3.655   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28 Do !
            O1  -CU1 -N2  -C12   -11.90  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29 Do !
            O1  -CU1 -N2  -C11  -141.90  1.40   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31 Do !
            N1  -CU1 -O2  -C17   115.40  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         37 Do !
            O2  -CU1 -N1  -C7     60.10  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         38 Do !
            O2  -CU1 -N1  -C8   -114.10  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         49 Do !
            N2  -CU1 -O1  -C1     85.20  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         58 Do !
            O4  -CU2 -O6  -C21     1.80  1.10   1.555   1.555   1.555   3.655
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         71 Do !
            O6  -CU2 -O4  -C19    -5.90  1.10   1.555   1.555   1.555   3.655
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        127 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Hexa-µ₂-acetato-bis(2-{[(2,2,6,6-tetramethylpiperidin-4-yl)imino]methyl}phenolato-κ³O,N,N')tetracopper(II) top

Crystal data top

[Cu₄(C₂H₃O₂)₆(C₁₆H₂₃N₂O)₂]	D_x = 1.456 Mg m⁻³
M_r = 1127.19	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbcn	Cell parameters from 4275 reflections
a = 31.2431 (6) Å	θ = 5.2–73.9°
b = 10.7872 (2) Å	µ = 2.40 mm⁻¹
c = 15.2556 (3) Å	T = 250 K
V = 5141.53 (18) Å³	Block, blue
Z = 4	0.1 × 0.1 × 0.05 mm
F(000) = 2336

Data collection top

Agilent Gemini S Ultra CCD diffractometer	5096 independent reflections
Radiation source: fine-focus sealed tube	3794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 74.0°, θ_min = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −37→38
T_min = 0.718, T_max = 1.000	k = −12→13
12793 measured reflections	l = −18→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0512P)² + 2.024P] where P = (F_o² + 2F_c²)/3
5096 reflections	(Δ/σ)_max = 0.002
305 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.684926 (12)	0.97594 (3)	0.05439 (3)	0.03840 (12)
Cu2	0.537735 (15)	0.84119 (4)	0.21238 (3)	0.05264 (14)
O1	0.71888 (6)	0.89442 (17)	−0.03139 (13)	0.0428 (4)
N1	0.72175 (7)	1.1220 (2)	0.05451 (16)	0.0419 (5)
O2	0.65473 (7)	0.81724 (18)	0.06203 (15)	0.0551 (6)
O3	0.59817 (7)	0.85329 (19)	0.14558 (16)	0.0592 (6)
O5	0.55006 (8)	0.9679 (2)	0.30302 (16)	0.0652 (6)
N2	0.64737 (7)	1.0688 (2)	0.13950 (15)	0.0410 (5)
H2	0.6248	1.0176	0.1529	0.049*
O4	0.51510 (8)	0.9730 (2)	0.13830 (16)	0.0665 (6)
C6	0.77655 (9)	1.0411 (2)	−0.04343 (18)	0.0398 (6)
C7	0.75839 (9)	1.1298 (2)	0.0151 (2)	0.0444 (6)
H7	0.7747	1.2014	0.0263	0.053*
O7	0.50945 (8)	0.7157 (2)	0.13683 (17)	0.0713 (7)
O6	0.55359 (8)	0.7104 (2)	0.29423 (17)	0.0677 (7)
C2	0.77766 (9)	0.8474 (3)	−0.12210 (18)	0.0447 (6)
H2A	0.7654	0.7700	−0.1355	0.054*
C12	0.62916 (10)	1.1791 (3)	0.0926 (2)	0.0487 (7)
C5	0.81565 (9)	1.0710 (3)	−0.0834 (2)	0.0501 (7)
H5	0.8288	1.1469	−0.0698	0.060*
C4	0.83518 (10)	0.9928 (3)	−0.1415 (2)	0.0545 (8)
H4	0.8611	1.0152	−0.1686	0.065*
C19	0.52267 (12)	1.0102 (3)	0.3548 (2)	0.0578 (8)
C17	0.62166 (10)	0.7826 (3)	0.1042 (2)	0.0491 (7)
C1	0.75614 (8)	0.9269 (2)	−0.06385 (17)	0.0385 (6)
C21	0.47211 (12)	0.6744 (3)	0.1491 (2)	0.0622 (9)
C11	0.67169 (11)	1.0900 (3)	0.2232 (2)	0.0507 (7)
C8	0.70868 (11)	1.2271 (3)	0.1102 (2)	0.0518 (8)
H8	0.7300	1.2945	0.1042	0.062*
C20	0.53536 (14)	1.1180 (4)	0.4132 (3)	0.0764 (11)
H20A	0.5659	1.1330	0.4078	0.115*
H20B	0.5286	1.0983	0.4737	0.115*
H20C	0.5198	1.1916	0.3956	0.115*
C15	0.64393 (14)	1.1303 (4)	0.2999 (2)	0.0746 (11)
H15A	0.6317	1.2110	0.2875	0.112*
H15B	0.6613	1.1352	0.3525	0.112*
H15C	0.6211	1.0705	0.3085	0.112*
C3	0.81596 (10)	0.8793 (3)	−0.1599 (2)	0.0520 (7)
H3	0.8294	0.8239	−0.1987	0.062*
C13	0.61459 (16)	1.1326 (4)	0.0033 (3)	0.0863 (14)
H13A	0.6390	1.1004	−0.0287	0.129*
H13B	0.6019	1.2004	−0.0293	0.129*
H13C	0.5936	1.0673	0.0110	0.129*
C16	0.69203 (16)	0.9646 (3)	0.2464 (3)	0.0882 (15)
H16A	0.6698	0.9024	0.2519	0.132*
H16B	0.7074	0.9718	0.3014	0.132*
H16C	0.7118	0.9405	0.2004	0.132*
C10	0.70695 (12)	1.1862 (3)	0.2050 (2)	0.0604 (9)
H10A	0.7021	1.2590	0.2421	0.073*
H10B	0.7347	1.1507	0.2212	0.073*
C18	0.61159 (14)	0.6453 (3)	0.1017 (3)	0.0853 (14)
H18A	0.5920	0.6285	0.0539	0.128*
H18B	0.5985	0.6207	0.1567	0.128*
H18C	0.6378	0.5988	0.0929	0.128*
C9	0.66490 (11)	1.2754 (3)	0.0824 (2)	0.0597 (9)
H9A	0.6663	1.3016	0.0210	0.072*
H9B	0.6578	1.3485	0.1177	0.072*
C14	0.59022 (12)	1.2356 (3)	0.1380 (3)	0.0743 (11)
H14A	0.5704	1.1702	0.1542	0.111*
H14B	0.5762	1.2930	0.0984	0.111*
H14C	0.5993	1.2795	0.1903	0.111*
C22	0.45822 (14)	0.5698 (4)	0.0893 (3)	0.0949 (15)
H22A	0.4715	0.5800	0.0322	0.142*
H22B	0.4273	0.5712	0.0829	0.142*
H22C	0.4670	0.4911	0.1144	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0381 (2)	0.0315 (2)	0.0456 (2)	−0.00219 (16)	0.00017 (17)	−0.00167 (16)
Cu2	0.0483 (3)	0.0563 (3)	0.0533 (3)	−0.0039 (2)	0.0161 (2)	−0.0029 (2)
O1	0.0406 (10)	0.0352 (9)	0.0526 (11)	−0.0049 (8)	0.0037 (9)	−0.0039 (8)
N1	0.0436 (12)	0.0312 (11)	0.0509 (13)	−0.0015 (10)	−0.0007 (11)	−0.0017 (10)
O2	0.0482 (11)	0.0408 (11)	0.0763 (15)	−0.0090 (9)	0.0235 (11)	−0.0121 (10)
O3	0.0553 (13)	0.0473 (12)	0.0752 (15)	−0.0109 (10)	0.0275 (12)	−0.0134 (11)
O5	0.0609 (14)	0.0704 (15)	0.0645 (14)	−0.0060 (12)	0.0162 (12)	−0.0173 (12)
N2	0.0447 (12)	0.0349 (11)	0.0436 (12)	−0.0033 (10)	−0.0003 (10)	−0.0008 (10)
O4	0.0607 (15)	0.0753 (16)	0.0634 (14)	0.0009 (12)	0.0160 (12)	0.0144 (12)
C6	0.0365 (13)	0.0383 (14)	0.0444 (14)	0.0005 (11)	−0.0040 (11)	0.0067 (11)
C7	0.0458 (16)	0.0327 (13)	0.0546 (16)	−0.0046 (12)	−0.0058 (13)	0.0029 (12)
O7	0.0599 (14)	0.0801 (17)	0.0738 (16)	−0.0107 (13)	0.0179 (13)	−0.0235 (13)
O6	0.0575 (14)	0.0693 (15)	0.0763 (16)	0.0094 (12)	0.0200 (12)	0.0133 (13)
C2	0.0485 (16)	0.0435 (15)	0.0421 (14)	−0.0018 (13)	−0.0002 (13)	−0.0025 (12)
C12	0.0517 (17)	0.0435 (16)	0.0508 (16)	0.0091 (13)	−0.0024 (14)	−0.0015 (13)
C5	0.0420 (15)	0.0479 (16)	0.0604 (17)	−0.0067 (13)	−0.0029 (14)	0.0053 (14)
C4	0.0404 (16)	0.063 (2)	0.0597 (18)	−0.0049 (15)	0.0061 (14)	0.0055 (16)
C19	0.064 (2)	0.0598 (19)	0.0500 (17)	0.0040 (17)	0.0046 (16)	0.0012 (15)
C17	0.0456 (16)	0.0427 (15)	0.0590 (18)	−0.0077 (13)	0.0100 (15)	−0.0057 (14)
C1	0.0392 (13)	0.0367 (13)	0.0397 (13)	0.0001 (11)	−0.0047 (11)	0.0062 (11)
C21	0.058 (2)	0.062 (2)	0.066 (2)	−0.0063 (17)	0.0101 (17)	−0.0064 (17)
C11	0.0637 (19)	0.0457 (16)	0.0428 (15)	−0.0044 (15)	−0.0083 (14)	−0.0011 (13)
C8	0.0570 (18)	0.0350 (14)	0.0635 (19)	−0.0107 (13)	0.0066 (15)	−0.0096 (13)
C20	0.082 (3)	0.081 (3)	0.066 (2)	0.001 (2)	0.003 (2)	−0.023 (2)
C15	0.091 (3)	0.085 (3)	0.0481 (18)	−0.024 (2)	0.0074 (19)	−0.0137 (18)
C3	0.0524 (17)	0.0567 (18)	0.0470 (16)	0.0070 (15)	0.0061 (14)	0.0001 (14)
C13	0.121 (4)	0.065 (2)	0.073 (3)	0.029 (2)	−0.045 (3)	−0.0074 (19)
C16	0.136 (4)	0.053 (2)	0.076 (3)	0.007 (2)	−0.053 (3)	0.0001 (19)
C10	0.064 (2)	0.060 (2)	0.0573 (19)	−0.0151 (17)	−0.0029 (16)	−0.0133 (16)
C18	0.081 (3)	0.0451 (19)	0.130 (4)	−0.0187 (19)	0.047 (3)	−0.016 (2)
C9	0.066 (2)	0.0383 (16)	0.075 (2)	0.0073 (15)	0.0198 (18)	0.0052 (15)
C14	0.056 (2)	0.060 (2)	0.106 (3)	0.0113 (18)	0.015 (2)	0.003 (2)
C22	0.078 (3)	0.093 (3)	0.114 (4)	−0.021 (2)	0.012 (3)	−0.041 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.9004 (19)	C19—C20	1.518 (5)
Cu1—N1	1.951 (2)	C17—C18	1.515 (4)
Cu1—O2	1.958 (2)	C21—O6ⁱ	1.242 (4)
Cu1—N2	2.017 (2)	C21—C22	1.515 (5)
Cu2—Cu2ⁱ	2.6225 (9)	C11—C15	1.520 (5)
Cu2—O3	2.150 (2)	C11—C16	1.535 (5)
Cu2—O5	1.982 (2)	C11—C10	1.539 (4)
Cu2—O4	1.949 (2)	C8—H8	0.9900
Cu2—O7	1.986 (2)	C8—C10	1.513 (5)
Cu2—O6	1.948 (2)	C8—C9	1.524 (5)
O1—C1	1.313 (3)	C20—H20A	0.9700
N1—C7	1.295 (4)	C20—H20B	0.9700
N1—C8	1.474 (4)	C20—H20C	0.9700
O2—C17	1.273 (3)	C15—H15A	0.9700
O3—C17	1.232 (4)	C15—H15B	0.9700
O5—C19	1.251 (4)	C15—H15C	0.9700
N2—H2	0.9200	C3—H3	0.9400
N2—C12	1.500 (4)	C13—H13A	0.9700
N2—C11	1.503 (4)	C13—H13B	0.9700
O4—C19ⁱ	1.251 (4)	C13—H13C	0.9700
C6—C7	1.427 (4)	C16—H16A	0.9700
C6—C5	1.403 (4)	C16—H16B	0.9700
C6—C1	1.421 (4)	C16—H16C	0.9700
C7—H7	0.9400	C10—H10A	0.9800
O7—C21	1.262 (4)	C10—H10B	0.9800
O6—C21ⁱ	1.242 (4)	C18—H18A	0.9700
C2—H2A	0.9400	C18—H18B	0.9700
C2—C1	1.406 (4)	C18—H18C	0.9700
C2—C3	1.372 (4)	C9—H9A	0.9800
C12—C13	1.522 (5)	C9—H9B	0.9800
C12—C9	1.533 (5)	C14—H14A	0.9700
C12—C14	1.527 (4)	C14—H14B	0.9700
C5—H5	0.9400	C14—H14C	0.9700
C5—C4	1.368 (5)	C22—H22A	0.9700
C4—H4	0.9400	C22—H22B	0.9700
C4—C3	1.392 (4)	C22—H22C	0.9700
C19—O4ⁱ	1.251 (4)

O1—Cu1—N1	92.58 (9)	N2—C11—C15	114.1 (3)
O1—Cu1—O2	84.57 (8)	N2—C11—C16	105.7 (2)
O1—Cu1—N2	176.50 (9)	N2—C11—C10	108.1 (2)
N1—Cu1—O2	171.93 (10)	C15—C11—C16	108.1 (3)
N1—Cu1—N2	86.64 (9)	C15—C11—C10	110.7 (3)
O2—Cu1—N2	96.65 (9)	C16—C11—C10	109.8 (3)
O3—Cu2—Cu2ⁱ	175.77 (7)	N1—C8—H8	109.0
O5—Cu2—Cu2ⁱ	82.49 (7)	N1—C8—C10	109.7 (3)
O5—Cu2—O3	96.79 (9)	N1—C8—C9	110.6 (3)
O5—Cu2—O7	164.08 (10)	C10—C8—H8	109.0
O4—Cu2—Cu2ⁱ	85.84 (7)	C10—C8—C9	109.5 (3)
O4—Cu2—O3	89.98 (10)	C9—C8—H8	109.0
O4—Cu2—O5	88.41 (11)	C19—C20—H20A	109.5
O4—Cu2—O7	89.96 (12)	C19—C20—H20B	109.5
O7—Cu2—Cu2ⁱ	81.60 (7)	C19—C20—H20C	109.5
O7—Cu2—O3	99.04 (9)	H20A—C20—H20B	109.5
O6—Cu2—Cu2ⁱ	87.02 (7)	H20A—C20—H20C	109.5
O6—Cu2—O3	97.15 (10)	H20B—C20—H20C	109.5
O6—Cu2—O5	90.16 (11)	C11—C15—H15A	109.5
O6—Cu2—O4	172.85 (10)	C11—C15—H15B	109.5
O6—Cu2—O7	89.50 (12)	C11—C15—H15C	109.5
C1—O1—Cu1	129.15 (17)	H15A—C15—H15B	109.5
C7—N1—Cu1	125.01 (19)	H15A—C15—H15C	109.5
C7—N1—C8	117.5 (2)	H15B—C15—H15C	109.5
C8—N1—Cu1	117.26 (19)	C2—C3—C4	120.8 (3)
C17—O2—Cu1	132.64 (19)	C2—C3—H3	119.6
C17—O3—Cu2	136.77 (19)	C4—C3—H3	119.6
C19—O5—Cu2	124.0 (2)	C12—C13—H13A	109.5
Cu1—N2—H2	106.9	C12—C13—H13B	109.5
C12—N2—Cu1	107.93 (17)	C12—C13—H13C	109.5
C12—N2—H2	106.9	H13A—C13—H13B	109.5
C11—N2—Cu1	109.16 (18)	H13A—C13—H13C	109.5
C11—N2—H2	106.9	H13B—C13—H13C	109.5
C11—N2—C12	118.5 (2)	C11—C16—H16A	109.5
C19ⁱ—O4—Cu2	121.9 (2)	C11—C16—H16B	109.5
C5—C6—C7	117.6 (3)	C11—C16—H16C	109.5
C5—C6—C1	119.7 (3)	H16A—C16—H16B	109.5
C1—C6—C7	122.7 (3)	H16A—C16—H16C	109.5
N1—C7—C6	126.7 (3)	H16B—C16—H16C	109.5
N1—C7—H7	116.6	C11—C10—H10A	108.9
C6—C7—H7	116.6	C11—C10—H10B	108.9
C21—O7—Cu2	124.5 (2)	C8—C10—C11	113.2 (3)
C21ⁱ—O6—Cu2	120.5 (2)	C8—C10—H10A	108.9
C1—C2—H2A	119.0	C8—C10—H10B	108.9
C3—C2—H2A	119.0	H10A—C10—H10B	107.7
C3—C2—C1	122.0 (3)	C17—C18—H18A	109.5
N2—C12—C13	106.2 (2)	C17—C18—H18B	109.5
N2—C12—C9	108.0 (2)	C17—C18—H18C	109.5
N2—C12—C14	113.7 (3)	H18A—C18—H18B	109.5
C13—C12—C9	110.5 (3)	H18A—C18—H18C	109.5
C13—C12—C14	107.4 (3)	H18B—C18—H18C	109.5
C14—C12—C9	110.8 (3)	C12—C9—H9A	108.9
C6—C5—H5	119.1	C12—C9—H9B	108.9
C4—C5—C6	121.9 (3)	C8—C9—C12	113.2 (3)
C4—C5—H5	119.1	C8—C9—H9A	108.9
C5—C4—H4	120.6	C8—C9—H9B	108.9
C5—C4—C3	118.7 (3)	H9A—C9—H9B	107.8
C3—C4—H4	120.6	C12—C14—H14A	109.5
O5—C19—C20	118.1 (3)	C12—C14—H14B	109.5
O4ⁱ—C19—O5	125.5 (3)	C12—C14—H14C	109.5
O4ⁱ—C19—C20	116.3 (3)	H14A—C14—H14B	109.5
O2—C17—C18	116.3 (3)	H14A—C14—H14C	109.5
O3—C17—O2	124.1 (3)	H14B—C14—H14C	109.5
O3—C17—C18	119.6 (3)	C21—C22—H22A	109.5
O1—C1—C6	123.1 (2)	C21—C22—H22B	109.5
O1—C1—C2	120.0 (2)	C21—C22—H22C	109.5
C2—C1—C6	116.9 (2)	H22A—C22—H22B	109.5
O7—C21—C22	116.0 (3)	H22A—C22—H22C	109.5
O6ⁱ—C21—O7	126.2 (3)	H22B—C22—H22C	109.5
O6ⁱ—C21—C22	117.8 (3)

Cu1—O1—C1—C6	−5.6 (4)	O5—Cu2—O6—C21ⁱ	80.2 (3)
Cu1—O1—C1—C2	174.72 (19)	N2—Cu1—O1—C1	85.2 (15)
Cu1—N1—C7—C6	7.8 (4)	N2—Cu1—N1—C7	174.4 (3)
Cu1—N1—C8—C10	60.7 (3)	N2—Cu1—N1—C8	0.2 (2)
Cu1—N1—C8—C9	−60.1 (3)	N2—Cu1—O2—C17	1.7 (3)
Cu1—O2—C17—O3	7.8 (5)	N2—C12—C9—C8	7.7 (4)
Cu1—O2—C17—C18	−172.3 (3)	N2—C11—C10—C8	−2.6 (4)
Cu1—N2—C12—C13	44.4 (3)	O4—Cu2—O3—C17	−122.8 (3)
Cu1—N2—C12—C9	−74.1 (3)	O4—Cu2—O5—C19	80.8 (3)
Cu1—N2—C12—C14	162.4 (2)	O4—Cu2—O7—C21	−90.6 (3)
Cu1—N2—C11—C15	−165.8 (2)	O4—Cu2—O6—C21ⁱ	1.8 (11)
Cu1—N2—C11—C16	−47.1 (3)	C6—C5—C4—C3	−1.3 (5)
Cu1—N2—C11—C10	70.5 (3)	C7—N1—C8—C10	−113.9 (3)
Cu2ⁱ—Cu2—O3—C17	−131.2 (8)	C7—N1—C8—C9	125.2 (3)
Cu2ⁱ—Cu2—O5—C19	−5.2 (3)	C7—C6—C5—C4	−178.9 (3)
Cu2ⁱ—Cu2—O4—C19ⁱ	−1.9 (3)	C7—C6—C1—O1	0.7 (4)
Cu2ⁱ—Cu2—O7—C21	−4.8 (3)	C7—C6—C1—C2	−179.6 (3)
Cu2ⁱ—Cu2—O6—C21ⁱ	−2.2 (3)	O7—Cu2—O3—C17	−32.8 (4)
Cu2—O3—C17—O2	172.0 (2)	O7—Cu2—O5—C19	−3.5 (6)
Cu2—O3—C17—C18	−7.9 (6)	O7—Cu2—O4—C19ⁱ	79.7 (3)
Cu2—O5—C19—O4ⁱ	5.8 (5)	O7—Cu2—O6—C21ⁱ	−83.8 (3)
Cu2—O5—C19—C20	−172.6 (3)	O6—Cu2—O3—C17	57.8 (4)
Cu2—O7—C21—O6ⁱ	4.9 (6)	O6—Cu2—O5—C19	−92.2 (3)
Cu2—O7—C21—C22	−174.1 (3)	O6—Cu2—O4—C19ⁱ	−5.9 (11)
O1—Cu1—N1—C7	−9.0 (2)	O6—Cu2—O7—C21	82.3 (3)
O1—Cu1—N1—C8	176.8 (2)	C12—N2—C11—C15	70.2 (4)
O1—Cu1—O2—C17	−175.0 (3)	C12—N2—C11—C16	−171.1 (3)
O1—Cu1—N2—C12	−11.9 (15)	C12—N2—C11—C10	−53.5 (3)
O1—Cu1—N2—C11	−141.9 (14)	C5—C6—C7—N1	176.2 (3)
N1—Cu1—O1—C1	8.2 (2)	C5—C6—C1—O1	−177.7 (3)
N1—Cu1—O2—C17	115.4 (7)	C5—C6—C1—C2	2.0 (4)
N1—Cu1—N2—C12	65.23 (18)	C5—C4—C3—C2	1.5 (5)
N1—Cu1—N2—C11	−64.75 (18)	C1—C6—C7—N1	−2.2 (5)
N1—C8—C10—C11	−66.2 (4)	C1—C6—C5—C4	−0.4 (4)
N1—C8—C9—C12	62.4 (4)	C1—C2—C3—C4	0.2 (5)
O2—Cu1—O1—C1	−164.2 (2)	C11—N2—C12—C13	169.0 (3)
O2—Cu1—N1—C7	60.1 (8)	C11—N2—C12—C9	50.5 (3)
O2—Cu1—N1—C8	−114.1 (7)	C11—N2—C12—C14	−73.0 (4)
O2—Cu1—N2—C12	−122.17 (18)	C8—N1—C7—C6	−178.0 (3)
O2—Cu1—N2—C11	107.85 (18)	C15—C11—C10—C8	−128.3 (3)
O3—Cu2—O5—C19	170.6 (3)	C3—C2—C1—O1	177.8 (3)
O3—Cu2—O4—C19ⁱ	178.8 (3)	C3—C2—C1—C6	−2.0 (4)
O3—Cu2—O7—C21	179.5 (3)	C13—C12—C9—C8	−108.1 (3)
O3—Cu2—O6—C21ⁱ	177.1 (3)	C16—C11—C10—C8	112.3 (3)
O5—Cu2—O3—C17	148.8 (3)	C10—C8—C9—C12	−58.6 (4)
O5—Cu2—O4—C19ⁱ	−84.4 (3)	C9—C8—C10—C11	55.3 (4)
O5—Cu2—O7—C21	−6.5 (6)	C14—C12—C9—C8	133.0 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.92	1.96	2.789 (3)	149
C7—H7···O1ⁱⁱ	0.94	2.27	3.026 (3)	137
C7—H7···O2ⁱⁱ	0.94	2.59	3.460 (3)	153
C15—H15B···O1ⁱⁱⁱ	0.97	2.54	3.490 (4)	165

Symmetry codes: (ii) −x+3/2, y+1/2, z; (iii) x, −y+2, z+1/2.

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Crystal structure of a tetranuclear CuII complex with an O,N,N′-donor Schiff base ligand: hexa-μ2-acetato-bis­(2-{[(2,2,6,6-tetra­methyl­piperidin-4-yl)imino]­meth­yl}phenolato-κ3O,N,N′)tetra­copper(II)

Supporting information

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checkCIF/PLATON results

Crystal structure of a tetranuclear Cu^II complex with an O,N,N′-donor Schiff base ligand: hexa-μ₂-acetato-bis(2-{[(2,2,6,6-tetramethylpiperidin-4-yl)imino]methyl}phenolato-κ³O,N,N′)tetracopper(II)