metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

Tetra­kis­[μ3-2-(piperidin-1-yl)ethanolato]tetra­kis­[chloridocopper(II)]

aHefei University of Technology, Hefei, People's Republic of China
*Correspondence e-mail: luomei@pku.edu.cn

(Received 1 April 2014; accepted 22 April 2014; online 30 April 2014)

In the title tetra­nuclear compound, [Cu4(C7H14NO)4Cl4], each CuII cation is N,O-chelated by a piperidineethanolate anion and coordinated by a Cl anion and two O atoms from neighboring piperidine­ethano­late anions in a distorted NO3Cl square-pyramidal geometry. The deprotonated hydroxyl groups of the piperidineethanolate anions bridge CuII cations, forming the tetra­nuclear complex. All piperidine rings display a chair conformation. In the crystal, there are no significant inter­molecular inter­actions present. The crystal studied was an inversion twin refined with a minor component of 0.18 (5).

Related literature

For related metal complexes with piperidineethanolate as a chelating ligand, see: Yilmaz et al. (2010[Yilmaz, V. T., Soyer, E. & Buyukgungor, O. (2010). Polyhedron, 29, 920-924.]); Hamamci et al. (2008[Hamamci, S., Yilmaz, V. T. & Buyukgungor, O. (2008). Z. Naturforsch. Teil B, 63, 139-142.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu4(C7H14NO)4Cl4]

  • Mr = 908.72

  • Tetragonal, P 41 21 2

  • a = 13.9016 (2) Å

  • c = 38.8340 (9) Å

  • V = 7504.8 (3) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 5.47 mm−1

  • T = 293 K

  • 0.16 × 0.12 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.569, Tmax = 0.753

  • 66705 measured reflections

  • 6976 independent reflections

  • 6547 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.182

  • S = 1.17

  • 6976 reflections

  • 398 parameters

  • H-atom parameters constrained

  • Δρmax = 0.93 e Å−3

  • Δρmin = −0.81 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2913 Friedel pairs

  • Absolute structure parameter: 0.18 (5)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The piperidineethanol chelated metal complexes have been synthesized and their crystal structures have been reported previously (Hamamci et al., 2008; Yilmaz et al. 2010). We report here the structure of the title tetranuclear complex, a CuII complex N,O-chelated by the deprotonated piperidineethanol anion.

The molecular structure is shown in Fig. 1. Each CuII cation is N,O-chelated by a piperidineethnolate anion and coordinated by a Cl- anion and two O atoms from neighboring piperidineethanolate anions in a distorted NO3Cl square-pyramidal geometry. The Cu—O bond distances in the apical direction are significantly longer than those in the basal planes. The deprotonated hydroxyl groups of piperidineethanolate anions bridge the CuII cations to form the tetranuclear complex. The piperidine ring displays a chair conformation.

In the crystal, there are no significant intermolecular interactions present.

Related literature top

For related piperidineethnol-chelated complexes, see: Yilmaz et al. (2010); Hamamci et al. (2008).

Experimental top

1-(2-Hydroxyethyl)piperidine (1.292 g, 10 mmol) was added to a methanol solution (50 ml) of CuCl2.2H2O (0.853 g, 5 mmol). The mixture was refluxed for 48 h. The filtrate was slowly evaporated, the blue single crystals were obtained after a day.

Refinement top

H atoms were placed in calculated positions with C—H = 0.97 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
Tetrakis[µ3-2-(piperidin-1-yl)ethanolato]tetrakis[chloridocopper(II)] top
Crystal data top
[Cu4(C7H14NO)4Cl4]Dx = 1.609 Mg m3
Mr = 908.72Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P41212Cell parameters from 9940 reflections
Hall symbol: P 4abw 2nwθ = 3.9–68.8°
a = 13.9016 (2) ŵ = 5.47 mm1
c = 38.8340 (9) ÅT = 293 K
V = 7504.8 (3) Å3Prism, blue
Z = 80.16 × 0.12 × 0.08 mm
F(000) = 3744
Data collection top
Bruker APEXII CCD
diffractometer
6547 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.066
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 69.7°, θmin = 3.4°
Tmin = 0.569, Tmax = 0.753h = 1616
66705 measured reflectionsk = 1615
6976 independent reflectionsl = 4546
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.182 w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
6976 reflectionsΔρmax = 0.93 e Å3
398 parametersΔρmin = 0.81 e Å3
0 restraintsAbsolute structure: Flack (1983), 2913 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.18 (5)
Crystal data top
[Cu4(C7H14NO)4Cl4]Z = 8
Mr = 908.72Cu Kα radiation
Tetragonal, P41212µ = 5.47 mm1
a = 13.9016 (2) ÅT = 293 K
c = 38.8340 (9) Å0.16 × 0.12 × 0.08 mm
V = 7504.8 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6976 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6547 reflections with I > 2σ(I)
Tmin = 0.569, Tmax = 0.753Rint = 0.066
66705 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.182 w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P]
where P = (Fo2 + 2Fc2)/3
S = 1.17Δρmax = 0.93 e Å3
6976 reflectionsΔρmin = 0.81 e Å3
398 parametersAbsolute structure: Flack (1983), 2913 Friedel pairs
0 restraintsAbsolute structure parameter: 0.18 (5)
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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.03847 (9)0.68690 (8)0.03396 (3)0.0359 (3)
Cu20.19814 (9)0.54936 (8)0.03808 (3)0.0352 (3)
Cu30.19184 (8)0.68392 (9)0.03586 (3)0.0336 (3)
Cu40.05180 (8)0.52599 (8)0.03383 (4)0.0366 (3)
Cl10.02892 (19)0.84482 (16)0.04415 (7)0.0529 (6)
Cl20.20776 (19)0.39762 (16)0.05687 (8)0.0545 (6)
Cl30.34843 (16)0.68975 (19)0.04958 (7)0.0502 (6)
Cl40.10283 (18)0.5147 (2)0.04883 (9)0.0632 (8)
N10.3352 (5)0.5899 (5)0.05397 (18)0.0368 (16)
N20.0955 (6)0.6526 (5)0.0528 (2)0.0417 (18)
N30.1545 (5)0.8161 (5)0.05649 (18)0.0341 (15)
N40.0914 (5)0.3890 (5)0.04787 (19)0.0361 (16)
O10.1787 (4)0.6858 (4)0.02744 (15)0.0325 (12)
O20.0590 (4)0.5475 (4)0.02994 (15)0.0370 (13)
O30.0527 (4)0.6684 (4)0.02958 (17)0.0394 (14)
O40.1893 (4)0.5442 (4)0.02558 (15)0.0346 (12)
C10.2455 (6)0.7412 (6)0.0465 (2)0.040 (2)
H1A0.24780.80620.03740.048*
H1B0.22570.74450.07040.048*
C20.3414 (6)0.6967 (6)0.0440 (2)0.0364 (19)
H2A0.36560.70270.02070.044*
H2B0.38570.72960.05930.044*
C30.3439 (7)0.5788 (7)0.0916 (2)0.042 (2)
H3A0.29950.62280.10270.050*
H3B0.32520.51390.09790.050*
C40.4451 (8)0.5979 (8)0.1053 (3)0.051 (2)
H4A0.44790.58130.12950.062*
H4B0.45970.66590.10310.062*
C50.5196 (7)0.5397 (8)0.0857 (2)0.050 (2)
H5A0.58360.55770.09320.060*
H5B0.51060.47180.09040.060*
C60.5095 (5)0.5583 (8)0.0469 (2)0.043 (2)
H6A0.55600.51980.03440.051*
H6B0.52210.62550.04200.051*
C70.4089 (6)0.5323 (7)0.0357 (2)0.040 (2)
H7A0.39770.46460.04010.048*
H7B0.40280.54300.01110.048*
C80.0104 (7)0.4958 (6)0.0498 (3)0.046 (2)
H8A0.01580.43020.04150.055*
H8B0.00840.49440.07380.055*
C90.1069 (6)0.5489 (6)0.0455 (3)0.041 (2)
H9A0.15400.52170.06120.050*
H9B0.13040.54040.02220.050*
C100.1754 (6)0.7091 (7)0.0363 (3)0.044 (2)
H10A0.16000.77710.03760.053*
H10B0.17910.69180.01210.053*
C110.2722 (7)0.6925 (9)0.0527 (4)0.072 (4)
H11A0.32050.73100.04110.087*
H11B0.29000.62530.05040.087*
C120.2676 (9)0.7200 (9)0.0907 (4)0.074 (4)
H12A0.32920.70740.10160.089*
H12B0.25370.78810.09300.089*
C130.1893 (10)0.6614 (9)0.1083 (3)0.068 (3)
H13A0.18350.68190.13210.082*
H13B0.20740.59400.10820.082*
C140.0920 (7)0.6728 (7)0.0904 (2)0.047 (2)
H14A0.04610.62960.10110.056*
H14B0.06920.73800.09390.056*
C150.0002 (7)0.7326 (6)0.0510 (3)0.048 (2)
H15A0.00120.70910.07450.058*
H15B0.06540.73900.04280.058*
C160.0504 (7)0.8256 (7)0.0492 (3)0.048 (2)
H16A0.02200.86950.06570.057*
H16B0.04190.85300.02640.057*
C170.2152 (7)0.8908 (6)0.0417 (2)0.040 (2)
H17A0.20160.89620.01720.047*
H17B0.28220.87260.04420.047*
C180.1989 (8)0.9886 (7)0.0588 (3)0.055 (3)
H18A0.24021.03640.04820.066*
H18B0.13261.00850.05550.066*
C190.2207 (8)0.9825 (8)0.0970 (3)0.058 (3)
H19A0.28880.97030.10040.069*
H19B0.20481.04300.10800.069*
C200.1625 (8)0.9022 (7)0.1127 (3)0.050 (2)
H20A0.18100.89470.13670.060*
H20B0.09490.91960.11220.060*
C210.1757 (7)0.8089 (7)0.0946 (2)0.041 (2)
H21A0.13360.76120.10480.050*
H21B0.24150.78730.09770.050*
C220.2464 (7)0.4756 (7)0.0441 (3)0.048 (2)
H22A0.24850.49130.06840.057*
H22B0.31150.47380.03520.057*
C230.1969 (6)0.3820 (7)0.0384 (3)0.043 (2)
H23A0.22740.33260.05220.052*
H23B0.20280.36370.01430.052*
C240.0357 (8)0.3141 (7)0.0299 (3)0.051 (2)
H24A0.05190.31680.00560.061*
H24B0.03200.32980.03200.061*
C250.0498 (10)0.2113 (9)0.0421 (3)0.068 (3)
H25A0.00420.16980.03040.082*
H25B0.11410.19010.03600.082*
C260.0364 (8)0.2022 (7)0.0800 (3)0.055 (3)
H26A0.05530.13810.08720.066*
H26B0.03100.21080.08560.066*
C270.0955 (9)0.2757 (8)0.0991 (3)0.054 (3)
H27A0.16320.25990.09670.065*
H27B0.07950.27310.12340.065*
C280.0785 (7)0.3783 (7)0.0857 (2)0.044 (2)
H28A0.01370.39780.09170.053*
H28B0.12270.42160.09730.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0306 (6)0.0252 (6)0.0519 (7)0.0000 (5)0.0094 (6)0.0002 (6)
Cu20.0311 (6)0.0219 (6)0.0527 (7)0.0011 (5)0.0025 (6)0.0030 (5)
Cu30.0254 (6)0.0291 (6)0.0463 (7)0.0015 (5)0.0030 (5)0.0041 (5)
Cu40.0252 (6)0.0267 (6)0.0578 (8)0.0005 (5)0.0042 (6)0.0029 (6)
Cl10.0513 (14)0.0268 (10)0.0807 (17)0.0015 (9)0.0163 (12)0.0049 (11)
Cl20.0510 (14)0.0273 (11)0.0854 (18)0.0012 (10)0.0042 (12)0.0133 (11)
Cl30.0267 (10)0.0533 (14)0.0706 (15)0.0043 (10)0.0088 (10)0.0159 (12)
Cl40.0335 (12)0.0500 (14)0.106 (2)0.0035 (10)0.0059 (13)0.0126 (14)
N10.038 (4)0.036 (4)0.036 (4)0.010 (3)0.003 (3)0.001 (3)
N20.043 (4)0.027 (4)0.055 (4)0.007 (3)0.018 (4)0.002 (3)
N30.043 (4)0.021 (3)0.038 (4)0.000 (3)0.002 (3)0.004 (3)
N40.026 (4)0.034 (4)0.048 (4)0.008 (3)0.001 (3)0.002 (3)
O10.025 (3)0.025 (3)0.047 (3)0.008 (2)0.003 (2)0.001 (2)
O20.031 (3)0.026 (3)0.054 (3)0.010 (2)0.011 (3)0.008 (3)
O30.025 (3)0.026 (3)0.067 (4)0.009 (2)0.002 (3)0.005 (3)
O40.028 (3)0.026 (3)0.050 (3)0.008 (2)0.005 (2)0.005 (2)
C10.034 (5)0.027 (4)0.058 (5)0.004 (3)0.022 (4)0.003 (4)
C20.026 (4)0.039 (5)0.044 (5)0.006 (4)0.002 (3)0.011 (4)
C30.038 (5)0.039 (5)0.049 (5)0.006 (4)0.002 (4)0.002 (4)
C40.058 (6)0.050 (6)0.046 (5)0.000 (5)0.008 (5)0.005 (4)
C50.042 (5)0.057 (6)0.052 (6)0.011 (5)0.005 (4)0.008 (5)
C60.010 (4)0.053 (6)0.064 (6)0.005 (3)0.001 (4)0.013 (5)
C70.024 (4)0.049 (5)0.048 (5)0.009 (4)0.004 (4)0.005 (4)
C80.043 (5)0.023 (4)0.071 (6)0.004 (4)0.022 (5)0.002 (4)
C90.027 (4)0.028 (4)0.068 (6)0.006 (3)0.021 (4)0.005 (4)
C100.021 (4)0.039 (5)0.072 (6)0.003 (3)0.001 (4)0.008 (5)
C110.032 (5)0.063 (7)0.121 (11)0.027 (5)0.018 (6)0.035 (7)
C120.058 (7)0.049 (6)0.115 (11)0.015 (5)0.044 (7)0.003 (7)
C130.083 (9)0.053 (7)0.068 (7)0.001 (6)0.037 (7)0.004 (5)
C140.053 (6)0.038 (5)0.050 (5)0.005 (4)0.008 (4)0.002 (4)
C150.038 (5)0.026 (4)0.080 (7)0.003 (4)0.002 (5)0.012 (5)
C160.047 (5)0.034 (5)0.062 (6)0.023 (4)0.010 (5)0.020 (4)
C170.052 (6)0.029 (4)0.038 (5)0.005 (4)0.012 (4)0.002 (4)
C180.049 (6)0.034 (5)0.083 (7)0.010 (4)0.003 (5)0.005 (5)
C190.060 (6)0.048 (6)0.065 (6)0.005 (5)0.005 (5)0.022 (5)
C200.057 (6)0.047 (6)0.046 (5)0.008 (5)0.004 (5)0.016 (4)
C210.046 (5)0.041 (5)0.037 (4)0.008 (4)0.000 (4)0.001 (4)
C220.030 (5)0.040 (5)0.073 (7)0.013 (4)0.012 (4)0.010 (5)
C230.021 (4)0.048 (5)0.060 (6)0.018 (4)0.007 (4)0.007 (4)
C240.055 (6)0.046 (5)0.051 (5)0.011 (5)0.004 (5)0.004 (5)
C250.065 (8)0.069 (8)0.070 (7)0.034 (6)0.013 (6)0.001 (6)
C260.048 (6)0.043 (6)0.073 (7)0.009 (5)0.004 (5)0.016 (5)
C270.071 (7)0.044 (6)0.048 (6)0.006 (5)0.004 (5)0.013 (4)
C280.048 (5)0.038 (5)0.046 (5)0.001 (4)0.009 (4)0.009 (4)
Geometric parameters (Å, º) top
Cu1—O21.965 (6)C8—H8B0.9700
Cu1—O11.965 (5)C9—H9A0.9700
Cu1—N22.058 (7)C9—H9B0.9700
Cu1—Cl12.235 (2)C10—C111.507 (13)
Cu1—Cu22.9341 (17)C10—H10A0.9700
Cu2—O21.960 (6)C10—H10B0.9700
Cu2—O11.960 (5)C11—C121.529 (19)
Cu2—N12.081 (7)C11—H11A0.9700
Cu2—Cl22.236 (2)C11—H11B0.9700
Cu3—O31.961 (6)C12—C131.522 (18)
Cu3—O41.983 (6)C12—H12A0.9700
Cu3—N32.070 (7)C12—H12B0.9700
Cu3—Cl32.242 (2)C13—C141.528 (15)
Cu3—Cu42.9354 (17)C13—H13A0.9700
Cu4—O41.954 (6)C13—H13B0.9700
Cu4—O31.986 (6)C14—H14A0.9700
Cu4—N42.057 (7)C14—H14B0.9700
Cu4—Cl42.233 (3)C15—C161.472 (13)
N1—C31.476 (11)C15—H15A0.9700
N1—C71.482 (12)C15—H15B0.9700
N1—C21.536 (11)C16—H16A0.9700
N2—C91.478 (11)C16—H16B0.9700
N2—C141.488 (12)C17—C181.532 (13)
N2—C101.505 (12)C17—H17A0.9700
N3—C171.457 (11)C17—H17B0.9700
N3—C161.480 (12)C18—C191.514 (15)
N3—C211.512 (11)C18—H18A0.9700
N4—C241.474 (12)C18—H18B0.9700
N4—C281.488 (12)C19—C201.508 (15)
N4—C231.515 (10)C19—H19A0.9700
O1—C11.416 (9)C19—H19B0.9700
O2—C81.429 (10)C20—C211.488 (13)
O3—C151.421 (11)C20—H20A0.9700
O4—C221.434 (10)C20—H20B0.9700
C1—C21.473 (12)C21—H21A0.9700
C1—H1A0.9700C21—H21B0.9700
C1—H1B0.9700C22—C231.489 (14)
C2—H2A0.9700C22—H22A0.9700
C2—H2B0.9700C22—H22B0.9700
C3—C41.526 (14)C23—H23A0.9700
C3—H3A0.9700C23—H23B0.9700
C3—H3B0.9700C24—C251.518 (15)
C4—C51.519 (14)C24—H24A0.9700
C4—H4A0.9700C24—H24B0.9700
C4—H4B0.9700C25—C261.488 (15)
C5—C61.533 (13)C25—H25A0.9700
C5—H5A0.9700C25—H25B0.9700
C5—H5B0.9700C26—C271.508 (15)
C6—C71.510 (11)C26—H26A0.9700
C6—H6A0.9700C26—H26B0.9700
C6—H6B0.9700C27—C281.536 (13)
C7—H7A0.9700C27—H27A0.9700
C7—H7B0.9700C27—H27B0.9700
C8—C91.540 (12)C28—H28A0.9700
C8—H8A0.9700C28—H28B0.9700
O2—Cu1—O180.7 (2)C9—C8—H8B110.4
O2—Cu1—N286.1 (3)H8A—C8—H8B108.6
O1—Cu1—N2160.3 (3)N2—C9—C8110.7 (7)
O2—Cu1—Cl1172.5 (2)N2—C9—H9A109.5
O1—Cu1—Cl195.13 (18)C8—C9—H9A109.5
N2—Cu1—Cl196.4 (2)N2—C9—H9B109.5
O2—Cu1—Cu241.55 (17)C8—C9—H9B109.5
O1—Cu1—Cu241.56 (16)H9A—C9—H9B108.1
N2—Cu1—Cu2121.0 (2)N2—C10—C11113.4 (8)
Cl1—Cu1—Cu2132.50 (9)N2—C10—H10A108.9
O2—Cu2—O180.9 (2)C11—C10—H10A108.9
O2—Cu2—N1162.8 (3)N2—C10—H10B108.9
O1—Cu2—N185.8 (3)C11—C10—H10B108.9
O2—Cu2—Cl295.71 (18)H10A—C10—H10B107.7
O1—Cu2—Cl2171.88 (19)C10—C11—C12109.5 (11)
N1—Cu2—Cl296.0 (2)C10—C11—H11A109.8
O2—Cu2—Cu141.67 (16)C12—C11—H11A109.8
O1—Cu2—Cu141.69 (16)C10—C11—H11B109.8
N1—Cu2—Cu1122.2 (2)C12—C11—H11B109.8
Cl2—Cu2—Cu1132.67 (9)H11A—C11—H11B108.2
O3—Cu3—O481.3 (2)C13—C12—C11109.2 (9)
O3—Cu3—N384.2 (3)C13—C12—H12A109.8
O4—Cu3—N3160.5 (3)C11—C12—H12A109.8
O3—Cu3—Cl3172.2 (2)C13—C12—H12B109.8
O4—Cu3—Cl395.78 (18)C11—C12—H12B109.8
N3—Cu3—Cl396.9 (2)H12A—C12—H12B108.3
O3—Cu3—Cu442.29 (16)C12—C13—C14112.0 (9)
O4—Cu3—Cu441.42 (17)C12—C13—H13A109.2
N3—Cu3—Cu4120.5 (2)C14—C13—H13A109.2
Cl3—Cu3—Cu4132.62 (9)C12—C13—H13B109.2
O4—Cu4—O381.4 (2)C14—C13—H13B109.2
O4—Cu4—N484.4 (2)H13A—C13—H13B107.9
O3—Cu4—N4160.6 (3)N2—C14—C13113.4 (9)
O4—Cu4—Cl4173.4 (2)N2—C14—H14A108.9
O3—Cu4—Cl495.61 (18)C13—C14—H14A108.9
N4—Cu4—Cl497.1 (2)N2—C14—H14B108.9
O4—Cu4—Cu342.17 (16)C13—C14—H14B108.9
O3—Cu4—Cu341.63 (16)H14A—C14—H14B107.7
N4—Cu4—Cu3120.5 (2)O3—C15—C16106.3 (8)
Cl4—Cu4—Cu3133.15 (9)O3—C15—H15A110.5
C3—N1—C7111.3 (7)C16—C15—H15A110.5
C3—N1—C2110.2 (7)O3—C15—H15B110.5
C7—N1—C2111.3 (7)C16—C15—H15B110.5
C3—N1—Cu2109.9 (5)H15A—C15—H15B108.7
C7—N1—Cu2110.1 (5)C15—C16—N3112.1 (7)
C2—N1—Cu2103.8 (5)C15—C16—H16A109.2
C9—N2—C14112.1 (7)N3—C16—H16A109.2
C9—N2—C10110.3 (7)C15—C16—H16B109.2
C14—N2—C10110.2 (7)N3—C16—H16B109.2
C9—N2—Cu1104.8 (5)H16A—C16—H16B107.9
C14—N2—Cu1106.1 (6)N3—C17—C18112.0 (7)
C10—N2—Cu1113.2 (5)N3—C17—H17A109.2
C17—N3—C16115.2 (7)C18—C17—H17A109.2
C17—N3—C21108.7 (7)N3—C17—H17B109.2
C16—N3—C21112.6 (7)C18—C17—H17B109.2
C17—N3—Cu3109.6 (5)H17A—C17—H17B107.9
C16—N3—Cu3104.5 (5)C19—C18—C17110.3 (9)
C21—N3—Cu3105.7 (5)C19—C18—H18A109.6
C24—N4—C28109.5 (7)C17—C18—H18A109.6
C24—N4—C23110.4 (8)C19—C18—H18B109.6
C28—N4—C23110.6 (7)C17—C18—H18B109.6
C24—N4—Cu4112.8 (6)H18A—C18—H18B108.1
C28—N4—Cu4108.8 (5)C20—C19—C18109.3 (8)
C23—N4—Cu4104.7 (5)C20—C19—H19A109.8
C1—O1—Cu2109.0 (5)C18—C19—H19A109.8
C1—O1—Cu1125.4 (5)C20—C19—H19B109.8
Cu2—O1—Cu196.7 (2)C18—C19—H19B109.8
C8—O2—Cu2125.9 (6)H19A—C19—H19B108.3
C8—O2—Cu1110.8 (5)C21—C20—C19112.7 (9)
Cu2—O2—Cu196.8 (3)C21—C20—H20A109.1
C15—O3—Cu3111.4 (5)C19—C20—H20A109.1
C15—O3—Cu4125.0 (6)C21—C20—H20B109.1
Cu3—O3—Cu496.1 (2)C19—C20—H20B109.1
C22—O4—Cu4111.9 (5)H20A—C20—H20B107.8
C22—O4—Cu3122.7 (6)C20—C21—N3112.5 (8)
Cu4—O4—Cu396.4 (2)C20—C21—H21A109.1
O1—C1—C2109.4 (7)N3—C21—H21A109.1
O1—C1—H1A109.8C20—C21—H21B109.1
C2—C1—H1A109.8N3—C21—H21B109.1
O1—C1—H1B109.8H21A—C21—H21B107.8
C2—C1—H1B109.8O4—C22—C23104.5 (7)
H1A—C1—H1B108.2O4—C22—H22A110.8
C1—C2—N1109.8 (7)C23—C22—H22A110.8
C1—C2—H2A109.7O4—C22—H22B110.8
N1—C2—H2A109.7C23—C22—H22B110.8
C1—C2—H2B109.7H22A—C22—H22B108.9
N1—C2—H2B109.7C22—C23—N4110.8 (7)
H2A—C2—H2B108.2C22—C23—H23A109.5
N1—C3—C4113.6 (8)N4—C23—H23A109.5
N1—C3—H3A108.8C22—C23—H23B109.5
C4—C3—H3A108.8N4—C23—H23B109.5
N1—C3—H3B108.8H23A—C23—H23B108.1
C4—C3—H3B108.8N4—C24—C25116.7 (9)
H3A—C3—H3B107.7N4—C24—H24A108.1
C5—C4—C3111.2 (8)C25—C24—H24A108.1
C5—C4—H4A109.4N4—C24—H24B108.1
C3—C4—H4A109.4C25—C24—H24B108.1
C5—C4—H4B109.4H24A—C24—H24B107.3
C3—C4—H4B109.4C26—C25—C24111.9 (9)
H4A—C4—H4B108.0C26—C25—H25A109.2
C4—C5—C6109.9 (8)C24—C25—H25A109.2
C4—C5—H5A109.7C26—C25—H25B109.2
C6—C5—H5A109.7C24—C25—H25B109.2
C4—C5—H5B109.7H25A—C25—H25B107.9
C6—C5—H5B109.7C25—C26—C27111.1 (10)
H5A—C5—H5B108.2C25—C26—H26A109.4
C7—C6—C5109.2 (8)C27—C26—H26A109.4
C7—C6—H6A109.8C25—C26—H26B109.4
C5—C6—H6A109.8C27—C26—H26B109.4
C7—C6—H6B109.8H26A—C26—H26B108.0
C5—C6—H6B109.8C26—C27—C28112.3 (8)
H6A—C6—H6B108.3C26—C27—H27A109.1
N1—C7—C6111.9 (7)C28—C27—H27A109.1
N1—C7—H7A109.2C26—C27—H27B109.1
C6—C7—H7A109.2C28—C27—H27B109.1
N1—C7—H7B109.2H27A—C27—H27B107.9
C6—C7—H7B109.2N4—C28—C27114.0 (8)
H7A—C7—H7B107.9N4—C28—H28A108.7
O2—C8—C9106.9 (7)C27—C28—H28A108.7
O2—C8—H8A110.4N4—C28—H28B108.7
C9—C8—H8A110.4C27—C28—H28B108.7
O2—C8—H8B110.4H28A—C28—H28B107.6
O1—Cu1—Cu2—O2154.7 (4)N2—Cu1—O2—C816.2 (6)
N2—Cu1—Cu2—O237.2 (4)Cl1—Cu1—O2—C893.1 (16)
Cl1—Cu1—Cu2—O2173.6 (3)Cu2—Cu1—O2—C8132.6 (7)
O2—Cu1—Cu2—O1154.7 (4)O1—Cu1—O2—Cu216.7 (2)
N2—Cu1—Cu2—O1168.2 (4)N2—Cu1—O2—Cu2148.7 (3)
Cl1—Cu1—Cu2—O131.7 (3)Cl1—Cu1—O2—Cu239.4 (16)
O2—Cu1—Cu2—N1172.0 (3)O4—Cu3—O3—C15147.7 (6)
O1—Cu1—Cu2—N133.3 (3)N3—Cu3—O3—C1519.1 (6)
N2—Cu1—Cu2—N1134.9 (4)Cl3—Cu3—O3—C1579.0 (15)
Cl1—Cu1—Cu2—N11.5 (3)Cu4—Cu3—O3—C15131.4 (7)
O2—Cu1—Cu2—Cl233.7 (3)O4—Cu3—O3—Cu416.3 (2)
O1—Cu1—Cu2—Cl2171.6 (3)N3—Cu3—O3—Cu4150.5 (3)
N2—Cu1—Cu2—Cl23.5 (3)Cl3—Cu3—O3—Cu452.4 (15)
Cl1—Cu1—Cu2—Cl2139.90 (16)O4—Cu4—O3—C15138.1 (7)
O3—Cu3—Cu4—O4155.2 (4)N4—Cu4—O3—C1594.8 (10)
N3—Cu3—Cu4—O4170.2 (3)Cl4—Cu4—O3—C1536.0 (7)
Cl3—Cu3—Cu4—O433.2 (3)Cu3—Cu4—O3—C15121.5 (8)
O4—Cu3—Cu4—O3155.2 (4)O4—Cu4—O3—Cu316.6 (3)
N3—Cu3—Cu4—O334.6 (4)N4—Cu4—O3—Cu326.6 (10)
Cl3—Cu3—Cu4—O3171.6 (3)Cl4—Cu4—O3—Cu3157.5 (2)
O3—Cu3—Cu4—N4170.0 (4)O3—Cu4—O4—C22145.5 (6)
O4—Cu3—Cu4—N434.8 (3)N4—Cu4—O4—C2221.3 (6)
N3—Cu3—Cu4—N4135.4 (3)Cl4—Cu4—O4—C2282.0 (17)
Cl3—Cu3—Cu4—N41.6 (3)Cu3—Cu4—O4—C22129.1 (7)
O3—Cu3—Cu4—Cl431.5 (3)O3—Cu4—O4—Cu316.4 (2)
O4—Cu3—Cu4—Cl4173.4 (3)N4—Cu4—O4—Cu3150.4 (3)
N3—Cu3—Cu4—Cl43.2 (3)Cl4—Cu4—O4—Cu347.1 (17)
Cl3—Cu3—Cu4—Cl4140.15 (16)O3—Cu3—O4—C22137.8 (7)
O2—Cu2—N1—C372.1 (11)N3—Cu3—O4—C2295.2 (10)
O1—Cu2—N1—C3111.7 (6)Cl3—Cu3—O4—C2234.9 (7)
Cl2—Cu2—N1—C360.4 (6)Cu4—Cu3—O4—C22121.2 (7)
Cu1—Cu2—N1—C390.2 (6)O3—Cu3—O4—Cu416.6 (2)
O2—Cu2—N1—C7165.0 (8)N3—Cu3—O4—Cu426.0 (9)
O1—Cu2—N1—C7125.4 (6)Cl3—Cu3—O4—Cu4156.08 (19)
Cl2—Cu2—N1—C762.6 (6)Cu2—O1—C1—C245.4 (8)
Cu1—Cu2—N1—C7146.9 (5)Cu1—O1—C1—C2158.8 (5)
O2—Cu2—N1—C245.8 (11)O1—C1—C2—N152.2 (10)
O1—Cu2—N1—C26.2 (5)C3—N1—C2—C185.9 (9)
Cl2—Cu2—N1—C2178.2 (5)C7—N1—C2—C1150.2 (7)
Cu1—Cu2—N1—C227.6 (6)Cu2—N1—C2—C131.7 (8)
O2—Cu1—N2—C911.8 (6)C7—N1—C3—C452.3 (10)
O1—Cu1—N2—C959.4 (11)C2—N1—C3—C471.6 (10)
Cl1—Cu1—N2—C9175.2 (6)Cu2—N1—C3—C4174.6 (6)
Cu2—Cu1—N2—C935.5 (7)N1—C3—C4—C551.6 (11)
O2—Cu1—N2—C14106.9 (6)C3—C4—C5—C653.8 (12)
O1—Cu1—N2—C1459.4 (10)C4—C5—C6—C758.0 (11)
Cl1—Cu1—N2—C1466.0 (6)C3—N1—C7—C656.8 (10)
Cu2—Cu1—N2—C1483.2 (6)C2—N1—C7—C666.5 (10)
O2—Cu1—N2—C10132.1 (6)Cu2—N1—C7—C6179.0 (7)
O1—Cu1—N2—C10179.7 (7)C5—C6—C7—N159.9 (10)
Cl1—Cu1—N2—C1055.0 (6)Cu2—O2—C8—C9154.7 (6)
Cu2—Cu1—N2—C10155.8 (5)Cu1—O2—C8—C939.2 (9)
O3—Cu3—N3—C17132.6 (6)C14—N2—C9—C878.3 (9)
O4—Cu3—N3—C17174.8 (7)C10—N2—C9—C8158.4 (8)
Cl3—Cu3—N3—C1755.2 (6)Cu1—N2—C9—C836.2 (9)
Cu4—Cu3—N3—C17155.2 (5)O2—C8—C9—N251.1 (10)
O3—Cu3—N3—C168.6 (6)C9—N2—C10—C1169.4 (11)
O4—Cu3—N3—C1650.8 (11)C14—N2—C10—C1154.9 (11)
Cl3—Cu3—N3—C16179.2 (6)Cu1—N2—C10—C11173.6 (8)
Cu4—Cu3—N3—C1631.2 (6)N2—C10—C11—C1258.9 (12)
O3—Cu3—N3—C21110.4 (6)C10—C11—C12—C1357.6 (12)
O4—Cu3—N3—C2168.2 (10)C11—C12—C13—C1455.2 (13)
Cl3—Cu3—N3—C2161.8 (5)C9—N2—C14—C1372.3 (10)
Cu4—Cu3—N3—C2187.8 (5)C10—N2—C14—C1351.0 (10)
O4—Cu4—N4—C24128.1 (6)Cu1—N2—C14—C13173.9 (7)
O3—Cu4—N4—C24171.0 (7)C12—C13—C14—N253.1 (12)
Cl4—Cu4—N4—C2458.3 (6)Cu3—O3—C15—C1642.3 (9)
Cu3—Cu4—N4—C24150.8 (5)Cu4—O3—C15—C16156.7 (6)
O4—Cu4—N4—C28110.1 (6)O3—C15—C16—N351.6 (11)
O3—Cu4—N4—C2867.2 (10)C17—N3—C16—C15155.0 (8)
Cl4—Cu4—N4—C2863.4 (6)C21—N3—C16—C1579.6 (10)
Cu3—Cu4—N4—C2887.5 (5)Cu3—N3—C16—C1534.7 (10)
O4—Cu4—N4—C238.1 (6)C16—N3—C17—C1869.0 (10)
O3—Cu4—N4—C2351.0 (11)C21—N3—C17—C1858.5 (10)
Cl4—Cu4—N4—C23178.4 (5)Cu3—N3—C17—C18173.6 (7)
Cu3—Cu4—N4—C2330.7 (6)N3—C17—C18—C1959.5 (11)
O2—Cu2—O1—C1147.9 (6)C17—C18—C19—C2054.4 (12)
N1—Cu2—O1—C121.1 (6)C18—C19—C20—C2153.5 (13)
Cl2—Cu2—O1—C182.0 (15)C19—C20—C21—N355.0 (12)
Cu1—Cu2—O1—C1131.2 (6)C17—N3—C21—C2056.3 (10)
O2—Cu2—O1—Cu116.7 (2)C16—N3—C21—C2072.6 (10)
N1—Cu2—O1—Cu1152.2 (3)Cu3—N3—C21—C20173.9 (7)
Cl2—Cu2—O1—Cu149.2 (15)Cu4—O4—C22—C2345.1 (9)
O2—Cu1—O1—C1135.8 (6)Cu3—O4—C22—C23158.7 (6)
N2—Cu1—O1—C187.6 (10)O4—C22—C23—N453.0 (10)
Cl1—Cu1—O1—C138.0 (6)C24—N4—C23—C22157.2 (8)
Cu2—Cu1—O1—C1119.1 (7)C28—N4—C23—C2281.5 (9)
O2—Cu1—O1—Cu216.7 (2)Cu4—N4—C23—C2235.5 (9)
N2—Cu1—O1—Cu231.5 (9)C28—N4—C24—C2550.4 (11)
Cl1—Cu1—O1—Cu2157.1 (2)C23—N4—C24—C2571.5 (11)
O1—Cu2—O2—C8138.5 (7)Cu4—N4—C24—C25171.7 (7)
N1—Cu2—O2—C898.5 (10)N4—C24—C25—C2652.0 (14)
Cl2—Cu2—O2—C834.0 (6)C24—C25—C26—C2750.6 (13)
Cu1—Cu2—O2—C8121.8 (7)C25—C26—C27—C2852.0 (12)
O1—Cu2—O2—Cu116.7 (2)C24—N4—C28—C2750.2 (11)
N1—Cu2—O2—Cu123.3 (10)C23—N4—C28—C2771.7 (10)
Cl2—Cu2—O2—Cu1155.8 (2)Cu4—N4—C28—C27173.9 (7)
O1—Cu1—O2—C8149.3 (6)C26—C27—C28—N453.0 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Cl30.972.753.638 (9)153
C2—H2B···Cl4i0.972.973.689 (9)132
C3—H3B···Cl20.972.803.428 (10)124
C7—H7A···Cl20.972.873.464 (9)120
C9—H9B···Cl40.972.813.696 (11)153
C10—H10A···Cl10.972.803.423 (9)123
C14—H14B···Cl10.972.793.432 (10)124
C16—H16B···Cl10.972.753.647 (11)154
C17—H17B···Cl30.972.713.367 (9)125
C21—H21B···Cl30.972.753.400 (10)125
C23—H23A···Cl2ii0.972.943.765 (9)144
C23—H23B···Cl20.972.813.708 (10)155
C24—H24B···Cl40.972.833.469 (11)124
C28—H28A···Cl40.972.843.465 (10)123
Symmetry codes: (i) y, x+1, z; (ii) y, x, z.

Experimental details

Crystal data
Chemical formula[Cu4(C7H14NO)4Cl4]
Mr908.72
Crystal system, space groupTetragonal, P41212
Temperature (K)293
a, c (Å)13.9016 (2), 38.8340 (9)
V3)7504.8 (3)
Z8
Radiation typeCu Kα
µ (mm1)5.47
Crystal size (mm)0.16 × 0.12 × 0.08
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.569, 0.753
No. of measured, independent and
observed [I > 2σ(I)] reflections
66705, 6976, 6547
Rint0.066
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.182, 1.17
No. of reflections6976
No. of parameters398
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.93, 0.81
Absolute structureFlack (1983), 2913 Friedel pairs
Absolute structure parameter0.18 (5)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported financially by Hefei University of Technology, China.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationHamamci, S., Yilmaz, V. T. & Buyukgungor, O. (2008). Z. Naturforsch. Teil B, 63, 139–142.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationYilmaz, V. T., Soyer, E. & Buyukgungor, O. (2010). Polyhedron, 29, 920–924.  Web of Science CSD CrossRef CAS

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