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Acta Cryst. (2007). E63, m1972-m1973    [ doi:10.1107/S1600536807029819 ]

Di-[mu]-chlorido-bis{aqua[5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinato]copper(II)}

Y. Zhao, K. Qian, Y.-G. Tu, J.-K. Li and W. Liu

Abstract top

In the title centrosymmetric complex, [Cu2(C15H18N3O3)2(H2O)2Cl2], the bridging Cu2Cl2 ring, which is exactly planar by virtue of a crystallographic inversion center, has two different Cu-Cl distances. The dihedral angle between the pyridine and imidazole ring planes is 2.49 (4)°. In the crystal structure, intermolecular O-H...O hydrogen bonds link dimer molecules into a one-dimensional chain in the c-axis direction. The atoms of the isopropyl and ethyl groups are disordered over two sites with approximate occupancies of 0.75:0.25 and 0.5:0.5, respectively.

Comment top

The synthesis and characterization of binuclear copper(II) complexes has made an impact on bio-inorganic chemistry (Solomon et al., 1996). The exchange mechanism of bridged copper(II) complexes has been published (Johnson et al., 1984). An excellent treatise on the orbital interaction in metal dimer complexes was also published (Hoffman et al., 1975).

The molecular structure is shown in Fig. 1. The bridging Cu2Cl2 unit is exactly planar. The Cu1—Cl1 and Cu1—Cl1i [symmetry code: (i) 1 − x, 1 − y, 1 − z] distances are not equal [2.2301 (11) and 2.7249 (11) Å]. The distance between Cu and Cu1i is less than the value in di-u-chloro- bis{chloro[1,2-diphenyl-2-(phenylamino)ethanoximato]copper(II)} (Puschmann, Batsanov et al., 2001) [3.4275 (4) versus 3.5172 (4) Å] and is longer than that in di-[µ]-chloro-bis{chloro[1,2-diphenyl-2-(4-chlorophenylamino) ethanoximato]copper(II)} [3.3514 (3) Å] [Puschmann, Howard et al., 2001]. In the asymmetric unit, the dihedral angle between the plane of the pyridine ring and the imidazole group plane is 2.49 (4) °. In the crystal structure, there is a O4—H4B···O1ii [symmetry code: (ii) x, y, z + 1] hydrogen bond (H4B···O1 = 1.70 Å), which links molecules into chains in the c axis direction.

Related literature top

For background information, see: Solomon et al. (1996); Hay et al. (1995); Johnson et al. (1984). For related structures, see: Puschmann, Batsanov et al. (2001); Puschmann, Howard et al. (2001).

Experimental top

A heavy-walled Pyrex tube containing a mixture of CuCl2·2H2O (0.02 g), 5-Ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)- nicotinic acid (0.03 g), 0.65 mol/l NaOH solution (0.3 ml) and H2O (2 ml) was frozen in liquid N2, sealed under vacuum and placed in an oven at 423 K. Blue single crystals suitable for X-ray analysis were then obtained after heating for one month.

Refinement top

The water H atoms were located in a difference Fourier map and included in the 'as found' positions with with Uiso(H)= 1.5Ueq(O); All other H atoms were included in calculated positions and refined as riding (C—H= 0.93–0.98 Å; N—H = 0.86 Å), with Uiso(H)= 1.5 Ueq(C) for methyl and 1.2 Ueq(C,N) for all other H atoms. Atoms C9 and C10 of the ethyl group are disordered over two sites with refined occupancies of 0.503 (7) and 0.497 (7) for the major and minor components, respectively. Atoms C13, C14 and C15 of the isopropyl group are disordered, with the ratio between the major and minor components refining to 75 (3):25 (3).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt (2005); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. : The molecular structure, showing 30% probability displacement ellipsoids. Hydrogen atoms and the minor components of disorder have been omitted [Symmetry code: (A) 1 − x, 1 − y, 1 − z].
[Figure 2] Fig. 2. : The crystal packing, viewed approximately along the a axis, showing the hydrogen bonded chain formed along the c axis. Hydrogen bonds are shown as dashed lines.
Di-µ-chloro-bis{aqua[5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro- 1H-imidazol-2-yl)nicotinato]copper(II)} top
Crystal data top
[Cu2(C15H18N3O3)2(H2O)2Cl2]F000 = 836
Mr = 810.68Dx = 1.514 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2342 reflections
a = 12.960 (2) Åθ = 2.3–22.5º
b = 13.2235 (19) ŵ = 1.40 mm−1
c = 10.4526 (16) ÅT = 291 (2) K
β = 97.012 (3)ºBlock, blue
V = 1778.0 (5) Å30.34 × 0.30 × 0.28 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		3487 independent reflections
Radiation source: fine-focus sealed tube2260 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 291(2) Kθmax = 26.0º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→15
Tmin = 0.647, Tmax = 0.695k = −13→16
9418 measured reflectionsl = −12→12
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0218P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3487 reflectionsΔρmax = 0.60 e Å−3
241 parametersΔρmin = −0.28 e Å−3
177 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu2(C15H18N3O3)2(H2O)2Cl2]V = 1778.0 (5) Å3
Mr = 810.68Z = 2
Monoclinic, P21/cMo Kα
a = 12.960 (2) ŵ = 1.40 mm−1
b = 13.2235 (19) ÅT = 291 (2) K
c = 10.4526 (16) Å0.34 × 0.30 × 0.28 mm
β = 97.012 (3)º
Data collection top
Bruker SMART CCD
diffractometer		3487 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2260 reflections with I > 2σ(I)
Tmin = 0.647, Tmax = 0.695Rint = 0.047
9418 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049177 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.01Δρmax = 0.60 e Å−3
3487 reflectionsΔρmin = −0.28 e Å−3
241 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C90.2667 (15)0.6115 (10)0.0561 (13)0.070 (2)0.503 (7)
H9A0.26190.6002−0.03610.084*0.503 (7)
H9B0.23420.55530.09540.084*0.503 (7)
C100.2156 (7)0.7105 (7)0.0849 (12)0.093 (2)0.503 (7)
H10A0.21630.71780.17640.139*0.503 (7)
H10B0.14500.71080.04420.139*0.503 (7)
H10C0.25290.76560.05220.139*0.503 (7)
C9'0.2633 (15)0.6291 (11)0.0901 (12)0.070 (2)0.497 (7)
H9'10.23570.56140.07540.084*0.497 (7)
H9'20.23700.65570.16640.084*0.497 (7)
C10'0.2247 (8)0.6943 (8)−0.0233 (12)0.093 (2)0.497 (7)
H10D0.23770.7640−0.00160.139*0.497 (7)
H10E0.15140.6840−0.04530.139*0.497 (7)
H10F0.26030.6765−0.09540.139*0.497 (7)
C130.9367 (14)0.5454 (8)0.3180 (14)0.0696 (14)0.75 (3)
H130.99380.54880.38860.084*0.75 (3)
C140.8774 (9)0.4486 (4)0.3335 (11)0.0709 (19)0.75 (3)
H14A0.82480.44040.26120.106*0.75 (3)
H14B0.84530.45170.41140.106*0.75 (3)
H14C0.92440.39230.33760.106*0.75 (3)
C150.9844 (10)0.5461 (10)0.1909 (8)0.091 (3)0.75 (3)
H15A1.03680.49460.19310.136*0.75 (3)
H15B1.01520.61100.17920.136*0.75 (3)
H15C0.93110.53320.12060.136*0.75 (3)
C13'0.944 (4)0.564 (2)0.316 (4)0.0696 (14)0.25 (3)
H13'0.98810.56550.39840.084*0.25 (3)
C14'0.905 (3)0.4542 (8)0.305 (3)0.0709 (19)0.25 (3)
H14D0.88540.43260.38620.106*0.25 (3)
H14E0.95870.41130.28050.106*0.25 (3)
H14F0.84510.45020.24030.106*0.25 (3)
C15'1.019 (2)0.585 (3)0.216 (3)0.091 (3)0.25 (3)
H15D0.98030.58700.13120.136*0.25 (3)
H15E1.06990.53250.21950.136*0.25 (3)
H15F1.05220.64900.23450.136*0.25 (3)
Cu10.57594 (3)0.60289 (3)0.47672 (4)0.04189 (16)
Cl10.42446 (7)0.60139 (7)0.55756 (9)0.0512 (3)
N10.5182 (2)0.6183 (2)0.2872 (3)0.0371 (7)
N20.7035 (2)0.6214 (2)0.4018 (3)0.0390 (7)
N30.7798 (2)0.6384 (2)0.2244 (3)0.0524 (9)
H3A0.78530.64390.14350.063*
O10.5822 (2)0.6509 (2)−0.1448 (3)0.0809 (10)
O20.7255 (2)0.6343 (2)−0.0127 (2)0.0674 (9)
O30.8461 (2)0.6231 (2)0.5567 (2)0.0669 (9)
O40.6551 (2)0.6095 (2)0.6469 (2)0.0786 (9)
H4A0.71790.61160.63970.118*
H4B0.63230.62760.71480.118*
C10.4177 (3)0.6166 (3)0.2445 (4)0.0473 (10)
H10.37020.61060.30390.057*
C20.3808 (3)0.6234 (3)0.1149 (4)0.0527 (11)
C30.4533 (3)0.6309 (3)0.0314 (4)0.0501 (11)
H30.43030.6356−0.05620.060*
C40.5595 (3)0.6318 (2)0.0701 (3)0.0386 (9)
C50.5886 (3)0.6261 (2)0.2032 (3)0.0325 (9)
C60.6938 (3)0.6284 (2)0.2732 (3)0.0366 (9)
C70.8071 (3)0.6269 (3)0.4445 (4)0.0492 (10)
C80.8673 (3)0.6389 (3)0.3283 (4)0.0537 (11)
C110.6306 (4)0.6391 (3)−0.0363 (4)0.0498 (11)
C120.9234 (3)0.7421 (3)0.3368 (4)0.0748 (14)
H12A0.95450.75350.25930.112*
H12B0.97640.74220.40950.112*
H12C0.87410.79480.34700.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C90.053 (3)0.089 (4)0.066 (5)−0.001 (3)0.000 (4)0.000 (4)
C100.073 (4)0.099 (4)0.103 (5)0.001 (3)−0.006 (4)0.008 (4)
C9'0.053 (3)0.089 (4)0.066 (5)−0.001 (3)0.000 (4)0.000 (4)
C10'0.073 (4)0.099 (4)0.103 (5)0.001 (3)−0.006 (4)0.008 (4)
C130.057 (3)0.089 (4)0.063 (3)0.012 (3)0.010 (2)0.008 (3)
C140.063 (5)0.077 (3)0.075 (4)0.017 (3)0.018 (3)0.000 (3)
C150.072 (4)0.114 (5)0.091 (4)0.004 (4)0.033 (3)−0.009 (4)
C13'0.057 (3)0.089 (4)0.063 (3)0.012 (3)0.010 (2)0.008 (3)
C14'0.063 (5)0.077 (3)0.075 (4)0.017 (3)0.018 (3)0.000 (3)
C15'0.072 (4)0.114 (5)0.091 (4)0.004 (4)0.033 (3)−0.009 (4)
Cu10.0406 (3)0.0545 (3)0.0317 (3)−0.0056 (3)0.0091 (2)−0.0009 (2)
Cl10.0510 (6)0.0529 (6)0.0537 (7)0.0025 (5)0.0230 (5)0.0001 (5)
N10.0360 (18)0.0410 (19)0.0342 (18)−0.0005 (15)0.0035 (14)0.0028 (13)
N20.0292 (17)0.058 (2)0.0291 (17)−0.0044 (15)0.0026 (13)0.0047 (14)
N30.0369 (19)0.091 (3)0.0300 (19)−0.0031 (18)0.0070 (15)0.0113 (16)
O10.076 (2)0.137 (3)0.0288 (17)0.016 (2)0.0030 (15)0.0025 (17)
O20.0510 (18)0.116 (3)0.0367 (17)0.0012 (18)0.0123 (14)0.0056 (15)
O30.0456 (18)0.118 (2)0.0346 (17)−0.0046 (17)−0.0075 (14)0.0030 (15)
O40.0585 (19)0.148 (3)0.0307 (16)−0.0201 (19)0.0088 (13)−0.0151 (17)
C10.035 (2)0.059 (3)0.048 (3)0.002 (2)0.0064 (19)0.007 (2)
C20.035 (2)0.062 (3)0.059 (3)0.001 (2)−0.006 (2)0.010 (2)
C30.053 (3)0.055 (3)0.038 (2)−0.001 (2)−0.012 (2)0.0102 (19)
C40.042 (2)0.038 (2)0.034 (2)0.0002 (18)−0.0023 (18)−0.0021 (16)
C50.034 (2)0.031 (2)0.031 (2)−0.0009 (16)0.0002 (16)0.0023 (15)
C60.033 (2)0.045 (2)0.032 (2)−0.0050 (18)0.0061 (17)0.0036 (16)
C70.045 (3)0.065 (3)0.037 (2)−0.003 (2)0.0028 (19)0.000 (2)
C80.036 (2)0.084 (3)0.041 (3)−0.003 (2)0.0043 (19)0.006 (2)
C110.067 (3)0.049 (3)0.033 (2)−0.001 (2)0.005 (2)0.0013 (18)
C120.054 (3)0.097 (4)0.072 (3)−0.035 (3)0.002 (2)0.015 (3)
Geometric parameters (Å, °) top
C9—C101.513 (9)C15'—H15F0.9600
C9—C21.538 (19)Cu1—N21.930 (3)
C9—H9A0.9700Cu1—O41.944 (2)
C9—H9B0.9700Cu1—N12.041 (3)
C10—H10A0.9600Cu1—Cl12.2301 (11)
C10—H10B0.9600Cu1—Cl1i2.7249 (11)
C10—H10C0.9600Cl1—Cu1i2.7249 (11)
C9'—C10'1.501 (9)N1—C11.325 (4)
C9'—C21.51 (2)N1—C51.345 (4)
C9'—H9'10.9700N2—C61.338 (4)
C9'—H9'20.9700N2—C71.364 (4)
C10'—H10D0.9600N3—C61.287 (4)
C10'—H10E0.9600N3—C81.472 (4)
C10'—H10F0.9600N3—H3A0.8600
C13—C141.511 (6)O1—C111.237 (4)
C13—C151.532 (7)O2—C111.227 (5)
C13—C81.540 (15)O3—C71.220 (4)
C13—H130.9800O4—H4A0.8257
C14—H14A0.9600O4—H4B0.8371
C14—H14B0.9600C1—C21.384 (5)
C14—H14C0.9600C1—H10.9300
C15—H15A0.9600C2—C31.362 (5)
C15—H15B0.9600C3—C41.387 (5)
C15—H15C0.9600C3—H30.9300
C13'—C81.42 (4)C4—C51.398 (4)
C13'—C14'1.533 (10)C4—C111.531 (5)
C13'—C15'1.536 (10)C5—C61.467 (4)
C13'—H13'0.9800C7—C81.530 (5)
C14'—H14D0.9600C8—C121.544 (5)
C14'—H14E0.9600C12—H12A0.9600
C14'—H14F0.9600C12—H12B0.9600
C15'—H15D0.9600C12—H12C0.9600
C15'—H15E0.9600
C10—C9—C2104.8 (10)C1—N1—C5119.9 (3)
C10—C9—H9A110.8C1—N1—Cu1123.7 (3)
C2—C9—H9A110.8C5—N1—Cu1116.4 (2)
C10—C9—H9B110.8C6—N2—C7107.1 (3)
C2—C9—H9B110.8C6—N2—Cu1115.9 (2)
H9A—C9—H9B108.9C7—N2—Cu1137.0 (3)
C10'—C9'—C2113.3 (13)C6—N3—C8109.5 (3)
C10'—C9'—H9'1108.9C6—N3—H3A125.2
C2—C9'—H9'1108.9C8—N3—H3A125.2
C10'—C9'—H9'2108.9Cu1—O4—H4A109.5
C2—C9'—H9'2108.9Cu1—O4—H4B126.0
H9'1—C9'—H9'2107.7H4A—O4—H4B121.4
C9'—C10'—H10D109.5N1—C1—C2122.5 (4)
C9'—C10'—H10E109.5N1—C1—H1118.8
H10D—C10'—H10E109.5C2—C1—H1118.8
C9'—C10'—H10F109.5C3—C2—C1116.7 (4)
H10D—C10'—H10F109.5C3—C2—C9'130.1 (6)
H10E—C10'—H10F109.5C1—C2—C9'113.0 (6)
C14—C13—C15111.2 (6)C3—C2—C9117.1 (7)
C14—C13—C8111.3 (9)C1—C2—C9125.8 (7)
C15—C13—C8110.9 (10)C2—C3—C4123.5 (4)
C14—C13—H13107.8C2—C3—H3118.3
C15—C13—H13107.8C4—C3—H3118.3
C8—C13—H13107.8C3—C4—C5115.3 (4)
C8—C13'—C14'116 (3)C3—C4—C11116.9 (3)
C8—C13'—C15'116 (3)C5—C4—C11127.8 (3)
C14'—C13'—C15'110.7 (10)N1—C5—C4122.1 (3)
C8—C13'—H13'104.0N1—C5—C6109.8 (3)
C14'—C13'—H13'104.0C4—C5—C6128.0 (3)
C15'—C13'—H13'104.0N3—C6—N2115.2 (3)
C13'—C14'—H14D109.5N3—C6—C5127.0 (3)
C13'—C14'—H14E109.5N2—C6—C5117.8 (3)
H14D—C14'—H14E109.5O3—C7—N2126.0 (4)
C13'—C14'—H14F109.5O3—C7—C8125.2 (4)
H14D—C14'—H14F109.5N2—C7—C8108.8 (3)
H14E—C14'—H14F109.5C13'—C8—N3114 (2)
C13'—C15'—H15D109.5C13'—C8—C7115.5 (13)
C13'—C15'—H15E109.5N3—C8—C799.4 (3)
H15D—C15'—H15E109.5N3—C8—C13110.4 (7)
C13'—C15'—H15F109.5C7—C8—C13109.4 (5)
H15D—C15'—H15F109.5C13'—C8—C12107.2 (11)
H15E—C15'—H15F109.5N3—C8—C12111.2 (3)
N2—Cu1—O489.01 (11)C7—C8—C12109.1 (3)
N2—Cu1—N179.86 (12)C13—C8—C12116.0 (6)
O4—Cu1—N1166.85 (11)O2—C11—O1125.1 (4)
N2—Cu1—Cl1172.96 (9)O2—C11—C4121.9 (3)
O4—Cu1—Cl192.56 (9)O1—C11—C4113.0 (4)
N1—Cu1—Cl197.67 (9)C8—C12—H12A109.5
N2—Cu1—Cl1i93.48 (9)C8—C12—H12B109.5
O4—Cu1—Cl1i99.06 (9)H12A—C12—H12B109.5
N1—Cu1—Cl1i88.66 (8)C8—C12—H12C109.5
Cl1—Cu1—Cl1i93.06 (3)H12A—C12—H12C109.5
Cu1—Cl1—Cu1i86.94 (3)H12B—C12—H12C109.5
O4—Cu1—Cl1—Cu1i−99.22 (9)Cu1—N2—C6—N3−178.5 (2)
N1—Cu1—Cl1—Cu1i89.06 (8)C7—N2—C6—C5−179.0 (3)
Cl1i—Cu1—Cl1—Cu1i0.0Cu1—N2—C6—C52.8 (4)
N2—Cu1—N1—C1−178.6 (3)N1—C5—C6—N3−177.8 (3)
O4—Cu1—N1—C1−146.0 (5)C4—C5—C6—N31.7 (6)
Cl1—Cu1—N1—C1−5.2 (3)N1—C5—C6—N20.8 (4)
Cl1i—Cu1—N1—C187.7 (3)C4—C5—C6—N2−179.7 (3)
N2—Cu1—N1—C54.3 (2)C6—N2—C7—O3−179.8 (4)
O4—Cu1—N1—C536.9 (6)Cu1—N2—C7—O3−2.2 (7)
Cl1—Cu1—N1—C5177.6 (2)C6—N2—C7—C80.1 (4)
Cl1i—Cu1—N1—C5−89.4 (2)Cu1—N2—C7—C8177.8 (3)
O4—Cu1—N2—C6−176.7 (3)C14'—C13'—C8—N3−56 (3)
N1—Cu1—N2—C6−3.7 (2)C15'—C13'—C8—N377 (3)
Cl1i—Cu1—N2—C684.3 (2)C14'—C13'—C8—C759 (4)
O4—Cu1—N2—C75.9 (4)C15'—C13'—C8—C7−169 (3)
N1—Cu1—N2—C7178.8 (4)C14'—C13'—C8—C1310 (14)
Cl1i—Cu1—N2—C7−93.2 (4)C15'—C13'—C8—C13143 (19)
C5—N1—C1—C2−0.5 (5)C14'—C13'—C8—C12−180 (3)
Cu1—N1—C1—C2−177.5 (3)C15'—C13'—C8—C12−47 (4)
N1—C1—C2—C30.8 (6)C6—N3—C8—C13'123.5 (10)
N1—C1—C2—C9'−175.0 (7)C6—N3—C8—C7−0.1 (4)
N1—C1—C2—C9173.5 (6)C6—N3—C8—C13114.7 (4)
C10'—C9'—C2—C3−29.3 (16)C6—N3—C8—C12−115.0 (4)
C10'—C9'—C2—C1145.7 (9)O3—C7—C8—C13'57 (2)
C10'—C9'—C2—C9−70 (3)N2—C7—C8—C13'−123 (2)
C10—C9—C2—C3−110.5 (10)O3—C7—C8—N3180.0 (4)
C10—C9—C2—C176.7 (12)N2—C7—C8—N30.0 (4)
C10—C9—C2—C9'36 (3)O3—C7—C8—C1364.3 (8)
C1—C2—C3—C40.0 (6)N2—C7—C8—C13−115.7 (7)
C9'—C2—C3—C4174.9 (8)O3—C7—C8—C12−63.6 (5)
C9—C2—C3—C4−173.4 (6)N2—C7—C8—C12116.4 (3)
C2—C3—C4—C5−1.0 (5)C14—C13—C8—C13'−179 (17)
C2—C3—C4—C11179.2 (3)C15—C13—C8—C13'−55 (16)
C1—N1—C5—C4−0.6 (5)C14—C13—C8—N3−62.2 (10)
Cu1—N1—C5—C4176.6 (2)C15—C13—C8—N362.2 (10)
C1—N1—C5—C6178.9 (3)C14—C13—C8—C746.3 (12)
Cu1—N1—C5—C6−3.9 (3)C15—C13—C8—C7170.6 (8)
C3—C4—C5—N11.3 (5)C14—C13—C8—C12170.2 (8)
C11—C4—C5—N1−178.9 (3)C15—C13—C8—C12−65.5 (12)
C3—C4—C5—C6−178.1 (3)C3—C4—C11—O2−175.5 (4)
C11—C4—C5—C61.7 (6)C5—C4—C11—O24.7 (6)
C8—N3—C6—N20.3 (5)C3—C4—C11—O15.0 (5)
C8—N3—C6—C5178.9 (3)C5—C4—C11—O1−174.8 (3)
C7—N2—C6—N3−0.2 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O1ii0.841.702.537 (4)174
O4—H4A···O30.831.972.759 (4)159
N3—H3A···O20.861.722.493 (4)148
Symmetry codes: (ii) x, y, z+1.
Table 1
Selected geometric parameters (Å, °) top
Cu1—N21.930 (3)Cu1—Cl12.2301 (11)
Cu1—O41.944 (2)Cu1—Cl1i2.7249 (11)
Cu1—N12.041 (3)
N2—Cu1—O489.01 (11)N2—Cu1—Cl1i93.48 (9)
N2—Cu1—N179.86 (12)O4—Cu1—Cl1i99.06 (9)
O4—Cu1—N1166.85 (11)N1—Cu1—Cl1i88.66 (8)
N2—Cu1—Cl1172.96 (9)Cl1—Cu1—Cl1i93.06 (3)
O4—Cu1—Cl192.56 (9)Cu1—Cl1—Cu1i86.94 (3)
N1—Cu1—Cl197.67 (9)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O1ii0.841.702.537 (4)174
O4—H4A···O30.831.972.759 (4)159
N3—H3A···O20.861.722.493 (4)148
Symmetry codes: (ii) x, y, z+1.
Acknowledgements top

The authors thank Dr Hai-Bin Song of Nankai University and Dr Jian-Ge Wang of Luoyang Normal University for their help.

references
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