Download citation
Download citation
link to html
The title compounds, [Cu(C15H12Cl2NO)2], (I), and [Cu(C17­H18NO2)2], (II), both adopt a compressed tetrahedral trans-[CuN2O2] coordination geometry, the mol­ecules having an umbrella conformation overall. These complexes differ from one another with respect to the 1-phenyl­ethyl­amine moieties, the direction of the benzene rings being either inside [in (I)] or inside and outside [in (II)] of the mol­ecules. The crystals of (I) and (II) have [Delta](R,R) and [Lambda](R,R) absolute configurations, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104026575/sq1180sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104026575/sq1180Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104026575/sq1180IIsup3.hkl
Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (4096) - rest discarded}

CCDC references: 259021; 259022

Comment top

Recent developments in functional switching materials (Sato et al., 2003) have shown that a good way to discover candidate metal complexes is to examine compounds that show any changes between two or more states, such as structural phase transitions, isomerism, mixed-valences and spin crossover. In this respect, bis(N-alkylsalicylideneimine)copper(II) complexes are potentially good examples, because some of them exhibit thermally induced structural phase transitions (Yamada, 1999), and structural isomers can be isolated (Chia et al., 1977). In addition, chirality (Barron & Buckingham, 2001) provides several structural and electronic modifications, and absolute asymmetric catalytic reactions (Nozaki et al., 1968) are also often susceptible to external physical influence (Avalos et al., 1998). For example, complexes incorporating 1-phenylethylamine ligands are suitable for studying the correlation between molecular structures and electronic properties (Akitsu et al., 2001; Akitsu et al., 2003), and optically active bis(N-alkylsalicylideneimine) complexes of CuII (Li et al., 1987), ZnII (Evans & Luneau, 2002; Sakiyama et al., 1990), PdII (Brunner et al., 2000) and RhV (Kühn et al., 1997) have been investigated in terms of stereochemistry, catalytic applications and second-harmonic generation. In this paper, we report the crystal structures of the title compounds, (I) and (II), having 1-phenylethylamine groups.

Both (I) (Table 1 and Fig. 1) and (II) (Table 2, and Figs. 2 and 3) adopt a compressed tetrahedral trans-[CuN2O2] coordination geometry. Both 1-phenylethylamine groups are folded along the molecular axis through the salicylideneaminate moiety, and the molecule of (I) adopts an umbrella conformation. On the other hand, complex (II), which crystallizes in the monoclinic system (space group P21 with Z = 4) contains two crystallographically independent molecules, which we denote molecules 1 (Cu1) and 2 (Cu2). The overall structure of molecule 1 differs from that of molecule 2. For both molecules of (II), one of the two 1-phenylethylamine groups is folded along the salicylideneaminate moiety, while the other is located towards the outside of the molecule. As the bond angles around the coordination environment show, complex (II) also adopts a tetrahedral trans-[CuN2O2] coordination geometry, which is closer to a tetrahedron than (I). The dihedral angles between the N1/Cu1/O1 and N2/Cu1/O2 planes are 45.0 (1)° for (I), and the dihedral angles between the N1/Cu1/O1 and N2/Cu1/O2 planes and the N3/Cu2/O5 and N4/Cu2/O6 planes are 39.80 (1) and 45.33 (1)°, respectively, for (II).

The degree of distortion of the trans-[CuN2O2] coordination environment in (I) and (II) results from both electronic effects of the 3,5-substituents and steric effects of the 1-phenylethylamine groups. However, these effects are complicated. For example, even 2-butylamine (Cheeseman et al., 1965) or 2-propylamine (Orioli & Sacconi, 1966) moieties can lead to a tetrahedral environment. In contrast, more bulky diphenylethylamine groups result in a planar environment (Fernandez et al., 2000). Most of the geometric parameters for (I) and (II) are comparable to analogous tetrahedral CuIIcomplexes (Yamada, 1999). Nevertheless only R-1-phenylethylamine was used for our preparations. The absolute configurations of the crystals of (I) and (II) examined were found to be Δ(R,R) and Λ(R,R), respectively. Both the related Cl-substituted ZnII complex (Evans & Luneau, 2001) and the CuII complex without 3-ethoxy substituents (Li et al., 1987) were reported to have Λ(R,R) configurations. Intra- and intermolecular hydrogen bonds are not detectable within van der Waals radii (Bondi, 1964) for either (I) or (II), and hence the crystal packing is dominated by weak van der Waals forces. Since no significant intermolecular interactions are found in either crystal, the factors determining the absolute configuration of the coordination environment are obscure at present.

In addition, DSC (differential scanning calorimetry) curves obtained by heating the brown precipitates of (I) and (II) showed endothermic peaks at 419 and 386 K, respectively. By analogy with similar CuII and NiII complexes (Yamada, 1999; Akitsu & Einaga, 2004; Arai et al., 1972), these features are attributed to thermally induced structural phase transitions. The structural change seems to be irreversible for both cases, though there are no intermolecular hydrogen bonds in the crystals. Moreover, whether conversion occurs between Λ(R,R) or Δ(R,R) forms during the phase transition is still unclear.

Experimental top

For the preparation of (I), treatment of equimolar quantities of copper(II) acetate (0.91 g, 5.00 mmol), R-1-phenylethylamine (1.21 g, 10.0 mmol) and 3,5-dichlorosalicylaldehyde (1.91 g, 10.0 mmol) in methanol (150 ml) at 318 K for 2 h gave rise to a brown precipitate. Plate-like brown crystals were grown by the slow evaporation of a methanol solution at 278 K overnight. Analysis found: C 55.37, H 3.98, N 4.09%; calculated for C30H24Cl4CuN2O2: C 55.44, H 3.72, N 4.31%. IR (KBr): 1623 cm−1 (C=N). m.p. 556 K (decomposed). The same preparation procedure was used for (II), except that 3-ethoxysalicylaldehyde (1.66 g, 10.0 mmol) was used instead of 3,5-diclrorosalicylaldehyde. Analysis found: C 67.84, H 6.12, N 4.59%; calculated for C34H36CuN2O4: C 68.04, H 6.05, N 4.67%; IR (KBr): 1636 cm−1 (C=N). m.p. 542 K (decomposed).

Refinement top

H atoms were placed in calculated positions (with C—H = 0.950 Å) and were included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom). The C atoms of the phenyl groups, namely C1–C6, C10–C15, C16–C21 and C25–C30 for (I), and C1–C6, C10–C15, C16–C21, C25–C30, C35–C40, C44–C49, C50–C55 and C59–C64 for (II), were treated as rigid groups of anisotropic atoms. Because of the remarkable plate-like shape and relatively poor quality of crystals for (II), we employed the present data as the best result. Since we do not have another good single-crystal, we could not recollect the data.

Computing details top

For both compounds, data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular structure of (II) (molecule 1), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. The molecular structure of (II) (molecule 2), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
(I) Bis[(R)-3,5-dichloro-N-(1-phenylethyl)salicylideneaminato-κ2N,O)]copper(II) top
Crystal data top
[Cu(C15H12Cl2NO)2]F(000) = 662.0
Mr = 649.86Dx = 1.521 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 11.166 (5) Åθ = 10.2–14.8°
b = 14.852 (7) ŵ = 1.18 mm1
c = 8.636 (4) ÅT = 297 K
β = 97.89 (4)°Plate, brown
V = 1418.6 (11) Å30.30 × 0.30 × 0.20 mm
Z = 2
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.020
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 514
Tmin = 0.709, Tmax = 0.790k = 019
3771 measured reflectionsl = 1111
3387 independent reflections3 standard reflections every 150 reflections
2958 reflections with I > 2σ(I) intensity decay: 0.1%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.597P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.034(Δ/σ)max = 0.002
wR(F2) = 0.093Δρmax = 0.63 e Å3
S = 1.05Δρmin = 0.50 e Å3
2958 reflectionsAbsolute structure: Flack (1983), 3387 Friedel pairs
304 parametersAbsolute structure parameter: 0.01 (2)
H-atom parameters constrained
Crystal data top
[Cu(C15H12Cl2NO)2]V = 1418.6 (11) Å3
Mr = 649.86Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.166 (5) ŵ = 1.18 mm1
b = 14.852 (7) ÅT = 297 K
c = 8.636 (4) Å0.30 × 0.30 × 0.20 mm
β = 97.89 (4)°
Data collection top
Rigaku AFC-7R
diffractometer
2958 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.020
Tmin = 0.709, Tmax = 0.7903 standard reflections every 150 reflections
3771 measured reflections intensity decay: 0.1%
3387 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.63 e Å3
S = 1.05Δρmin = 0.50 e Å3
2958 reflectionsAbsolute structure: Flack (1983), 3387 Friedel pairs
304 parametersAbsolute structure parameter: 0.01 (2)
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.43069 (4)0.39418 (3)0.81436 (5)0.0292 (1)
Cl10.0308 (2)0.6253 (1)0.2394 (2)0.0815 (6)
Cl20.0998 (1)0.2891 (1)0.4671 (2)0.0550 (3)
Cl30.6764 (1)0.3227 (1)1.6221 (1)0.0476 (3)
Cl40.83029 (9)0.3584 (1)1.0607 (1)0.0514 (3)
O10.3205 (3)0.3636 (2)0.6361 (3)0.0343 (6)
O20.5777 (2)0.3766 (2)0.9449 (3)0.0339 (7)
N10.4876 (3)0.5024 (3)0.7085 (4)0.0323 (7)
N20.3317 (3)0.3519 (3)0.9741 (4)0.0295 (7)
C10.2622 (2)0.4233 (2)0.5367 (3)0.0313 (8)
C20.1517 (2)0.3970 (2)0.4551 (3)0.0385 (8)
C30.0828 (2)0.4581 (2)0.3588 (3)0.045 (1)
C40.1242 (3)0.5455 (2)0.3440 (4)0.048 (1)
C50.2347 (3)0.5718 (2)0.4255 (4)0.048 (1)
C60.3037 (2)0.5107 (2)0.5219 (3)0.0364 (9)
C70.4202 (4)0.5414 (3)0.5973 (5)0.0375 (10)
C80.6029 (4)0.5447 (3)0.7783 (5)0.0343 (9)
C90.6561 (4)0.6118 (4)0.6732 (6)0.046 (1)
C100.5881 (3)0.5857 (2)0.9364 (3)0.0368 (9)
C110.6860 (2)0.5847 (2)1.0546 (4)0.049 (1)
C120.6754 (3)0.6227 (3)1.1992 (3)0.058 (1)
C130.5669 (4)0.6617 (3)1.2256 (3)0.061 (2)
C140.4690 (3)0.6627 (3)1.1074 (4)0.055 (1)
C150.4795 (2)0.6248 (2)0.9628 (3)0.042 (1)
C160.5943 (2)0.3588 (2)1.0980 (2)0.0328 (8)
C170.7133 (2)0.3534 (2)1.1698 (3)0.0347 (9)
C180.7380 (2)0.3408 (3)1.3305 (3)0.0386 (10)
C190.6437 (2)0.3336 (2)1.4194 (2)0.0365 (9)
C200.5246 (2)0.3389 (2)1.3476 (3)0.0329 (9)
C210.4999 (2)0.3515 (2)1.1869 (3)0.0311 (8)
C220.3736 (4)0.3445 (3)1.1191 (5)0.0331 (9)
C230.2004 (4)0.3379 (3)0.9222 (5)0.0325 (9)
C240.1327 (4)0.2871 (4)1.0360 (6)0.043 (1)
C250.1387 (3)0.4273 (2)0.8757 (4)0.040 (1)
C260.0286 (3)0.4245 (3)0.7787 (5)0.058 (2)
C270.0299 (3)0.5041 (4)0.7289 (5)0.082 (2)
C280.0216 (5)0.5865 (3)0.7761 (6)0.094 (3)
C290.1317 (5)0.5893 (2)0.8731 (7)0.094 (3)
C300.1903 (3)0.5098 (3)0.9229 (5)0.059 (1)
H10.00720.44010.30310.0538*
H20.26310.63160.41540.0572*
H30.44960.59630.56020.0451*
H40.66010.49730.79830.0411*
H50.66850.58300.57840.0553*
H60.73110.63350.72480.0553*
H70.60180.66080.65070.0553*
H80.76020.55811.03650.0583*
H90.74240.62201.28000.0701*
H100.55970.68771.32440.0730*
H110.39480.68941.12540.0655*
H120.41260.62550.88200.0506*
H130.81940.33721.37960.0463*
H140.46020.33401.40830.0395*
H150.31680.33331.18920.0398*
H160.19440.30250.82980.0390*
H170.05080.27940.99130.0518*
H180.13600.32031.13050.0518*
H190.16910.22981.05730.0518*
H200.00660.36810.74640.0699*
H210.10520.50210.66270.0989*
H220.01840.64090.74210.1134*
H230.16700.64570.90540.1125*
H240.26550.51170.98910.0710*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0276 (2)0.0322 (2)0.0267 (2)0.0016 (2)0.0001 (2)0.0028 (2)
Cl10.071 (1)0.076 (1)0.087 (1)0.0217 (9)0.0264 (9)0.0226 (10)
Cl20.0543 (7)0.0502 (8)0.0556 (7)0.0159 (6)0.0100 (6)0.0042 (6)
Cl30.0562 (7)0.0596 (8)0.0251 (5)0.0054 (6)0.0009 (5)0.0012 (5)
Cl40.0264 (4)0.0864 (10)0.0422 (6)0.0013 (5)0.0073 (4)0.0024 (6)
O10.038 (1)0.033 (2)0.030 (1)0.004 (1)0.004 (1)0.002 (1)
O20.028 (1)0.047 (2)0.026 (1)0.000 (1)0.0005 (10)0.005 (1)
N10.032 (2)0.035 (2)0.030 (2)0.002 (2)0.004 (1)0.001 (1)
N20.024 (1)0.033 (2)0.031 (2)0.002 (1)0.003 (1)0.003 (1)
C10.032 (2)0.033 (2)0.028 (2)0.000 (2)0.003 (2)0.001 (2)
C20.037 (2)0.045 (2)0.032 (2)0.001 (2)0.002 (2)0.005 (2)
C30.034 (2)0.060 (3)0.037 (2)0.005 (2)0.010 (2)0.005 (2)
C40.048 (3)0.053 (3)0.039 (3)0.014 (2)0.008 (2)0.009 (2)
C50.054 (3)0.042 (3)0.043 (3)0.002 (2)0.009 (2)0.013 (2)
C60.038 (2)0.036 (2)0.033 (2)0.000 (2)0.003 (2)0.003 (2)
C70.042 (2)0.034 (2)0.035 (2)0.007 (2)0.001 (2)0.006 (2)
C80.032 (2)0.035 (2)0.036 (2)0.001 (2)0.003 (2)0.001 (2)
C90.041 (2)0.054 (3)0.043 (2)0.014 (2)0.006 (2)0.002 (2)
C100.044 (2)0.030 (2)0.035 (2)0.009 (2)0.002 (2)0.002 (2)
C110.051 (3)0.048 (3)0.043 (3)0.009 (2)0.006 (2)0.002 (2)
C120.072 (4)0.058 (3)0.042 (3)0.017 (3)0.007 (3)0.000 (3)
C130.095 (5)0.047 (3)0.040 (3)0.010 (3)0.010 (3)0.005 (2)
C140.071 (4)0.042 (3)0.054 (3)0.001 (3)0.021 (3)0.006 (2)
C150.049 (3)0.032 (2)0.047 (3)0.001 (2)0.011 (2)0.004 (2)
C160.032 (2)0.037 (2)0.028 (2)0.000 (2)0.001 (2)0.002 (2)
C170.028 (2)0.043 (2)0.034 (2)0.000 (2)0.006 (2)0.001 (2)
C180.033 (2)0.046 (3)0.035 (2)0.001 (2)0.001 (2)0.001 (2)
C190.044 (2)0.040 (2)0.025 (2)0.006 (2)0.000 (2)0.001 (2)
C200.036 (2)0.038 (2)0.026 (2)0.003 (2)0.008 (2)0.001 (2)
C210.027 (2)0.036 (2)0.030 (2)0.001 (2)0.005 (1)0.001 (2)
C220.029 (2)0.039 (2)0.031 (2)0.002 (2)0.004 (2)0.004 (2)
C230.022 (2)0.037 (2)0.038 (2)0.002 (2)0.003 (2)0.004 (2)
C240.029 (2)0.051 (3)0.049 (3)0.004 (2)0.005 (2)0.004 (2)
C250.034 (2)0.048 (3)0.041 (2)0.013 (2)0.014 (2)0.006 (2)
C260.042 (3)0.078 (4)0.053 (3)0.023 (3)0.001 (2)0.003 (3)
C270.068 (4)0.108 (6)0.068 (4)0.052 (4)0.001 (3)0.015 (4)
C280.093 (6)0.082 (6)0.116 (6)0.060 (5)0.041 (5)0.047 (5)
C290.094 (6)0.052 (4)0.143 (8)0.028 (4)0.044 (5)0.022 (5)
C300.048 (3)0.042 (3)0.089 (4)0.010 (2)0.016 (3)0.010 (3)
Geometric parameters (Å, º) top
Cu1—O11.890 (3)C12—C131.390 (6)
Cu1—O21.878 (3)C12—H90.950
Cu1—N11.995 (4)C13—C141.390 (4)
Cu1—N21.984 (4)C13—H100.950
Cl1—C41.747 (4)C14—C151.390 (5)
Cl2—C21.712 (3)C14—H110.950
Cl3—C191.746 (2)C15—H120.950
Cl4—C171.714 (3)C16—C171.390 (3)
O1—C11.340 (4)C16—C211.390 (3)
O2—C161.336 (3)C17—C181.390 (3)
N1—C71.275 (6)C18—C191.390 (3)
N1—C81.484 (5)C18—H130.950
N2—C221.280 (5)C19—C201.390 (3)
N2—C231.488 (5)C20—C211.390 (3)
C1—C21.390 (4)C20—H140.950
C1—C61.390 (4)C21—C221.455 (4)
C2—C31.390 (4)C22—H150.950
C3—C41.390 (4)C23—C241.521 (7)
C3—H10.950C23—C251.524 (6)
C4—C51.390 (4)C23—H160.950
C5—C61.390 (4)C24—H170.950
C5—H20.950C24—H180.950
C6—C71.446 (5)C24—H190.950
C7—H30.950C25—C261.390 (4)
C8—C91.523 (7)C25—C301.390 (5)
C8—C101.525 (5)C26—C271.390 (6)
C8—H40.950C26—H200.950
C9—H50.950C27—C281.390 (7)
C9—H60.950C27—H210.950
C9—H70.950C28—C291.390 (7)
C10—C111.390 (4)C28—H220.950
C10—C151.390 (4)C29—C301.390 (5)
C11—C121.390 (5)C29—H230.950
C11—H80.950C30—H240.950
O1—Cu1—O2150.9 (1)C14—C13—H10120.0
O1—Cu1—N191.9 (1)C13—C14—C15120.0 (3)
O1—Cu1—N297.3 (1)C13—C14—H11120.0
O2—Cu1—N194.6 (1)C15—C14—H11120.0
O2—Cu1—N293.6 (1)C10—C15—C14120.0 (2)
N1—Cu1—N2144.7 (2)C10—C15—H12120.0
Cu1—O1—C1124.6 (2)C14—C15—H12120.0
Cu1—O2—C16127.8 (2)O2—C16—C17116.6 (2)
Cu1—N1—C7121.3 (3)O2—C16—C21123.3 (2)
Cu1—N1—C8117.9 (3)C17—C16—C21120.0 (2)
C7—N1—C8120.2 (4)Cl4—C17—C16120.4 (2)
Cu1—N2—C22122.9 (3)Cl4—C17—C18119.5 (2)
Cu1—N2—C23117.0 (2)C16—C17—C18120.0 (2)
C22—N2—C23119.7 (4)C17—C18—C19120.0 (2)
O1—C1—C2117.2 (2)C17—C18—H13120.0
O1—C1—C6122.6 (2)C19—C18—H13120.0
C2—C1—C6120.0 (2)Cl3—C19—C18119.4 (2)
Cl2—C2—C1121.1 (2)Cl3—C19—C20120.6 (2)
Cl2—C2—C3118.9 (2)C18—C19—C20120.0 (2)
C1—C2—C3120.0 (2)C19—C20—C21120.0 (2)
C2—C3—C4120.0 (2)C19—C20—H14120.0
C2—C3—H1120.0C21—C20—H14120.0
C4—C3—H1120.0C16—C21—C20120.0 (2)
Cl1—C4—C3119.9 (2)C16—C21—C22123.4 (2)
Cl1—C4—C5119.8 (2)C20—C21—C22116.1 (2)
C3—C4—C5120.0 (3)N2—C22—C21126.3 (4)
C4—C5—C6120.0 (2)N2—C22—H15116.9
C4—C5—H2120.0C21—C22—H15116.9
C6—C5—H2120.0N2—C23—C24115.5 (3)
C1—C6—C5120.0 (2)N2—C23—C25110.5 (3)
C1—C6—C7122.9 (3)N2—C23—H16106.5
C5—C6—C7117.0 (3)C24—C23—C25110.9 (3)
N1—C7—C6126.7 (4)C24—C23—H16106.5
N1—C7—H3116.6C25—C23—H16106.5
C6—C7—H3116.7C23—C24—H17109.5
N1—C8—C9115.0 (3)C23—C24—H18109.5
N1—C8—C10109.7 (3)C23—C24—H19109.5
N1—C8—H4106.6H17—C24—H18109.5
C9—C8—C10111.8 (4)H17—C24—H19109.5
C9—C8—H4106.6H18—C24—H19109.5
C10—C8—H4106.6C23—C25—C26117.6 (3)
C8—C9—H5109.5C23—C25—C30122.4 (3)
C8—C9—H6109.5C26—C25—C30120.0 (3)
C8—C9—H7109.5C25—C26—C27120.0 (3)
H5—C9—H6109.5C25—C26—H20120.0
H5—C9—H7109.5C27—C26—H20120.0
H6—C9—H7109.4C26—C27—C28120.0 (3)
C8—C10—C11118.8 (3)C26—C27—H21120.0
C8—C10—C15121.2 (3)C28—C27—H21120.0
C11—C10—C15120.0 (3)C27—C28—C29120.0 (4)
C10—C11—C12120.0 (3)C27—C28—H22120.0
C10—C11—H8120.0C29—C28—H22120.0
C12—C11—H8120.0C28—C29—C30120.0 (3)
C11—C12—C13120.0 (3)C28—C29—H23120.0
C11—C12—H9120.0C30—C29—H23120.0
C13—C12—H9120.0C25—C30—C29120.0 (3)
C12—C13—C14120.0 (3)C25—C30—H24120.0
C12—C13—H10120.0C29—C30—H24120.0
Cu1—O1—C1—C2153.3 (2)N2—C22—C21—C166.6 (7)
Cu1—O1—C1—C621.9 (4)N2—C22—C21—C20178.5 (4)
Cu1—O2—C16—C17176.7 (3)N2—C23—C25—C26159.5 (3)
Cu1—O2—C16—C211.0 (5)N2—C23—C25—C3018.6 (5)
Cu1—N1—C7—C66.7 (6)C1—C2—C3—C40.0 (4)
Cu1—N1—C8—C9166.1 (3)C1—C6—C5—C40.0 (5)
Cu1—N1—C8—C1066.9 (4)C2—C1—C6—C50.0 (4)
Cu1—N2—C22—C2110.0 (7)C2—C1—C6—C7177.0 (3)
Cu1—N2—C23—C24167.4 (3)C2—C3—C4—C50.0 (5)
Cu1—N2—C23—C2565.7 (4)C3—C2—C1—C60.0 (4)
Cl1—C4—C3—C2173.3 (2)C3—C4—C5—C60.0 (5)
Cl1—C4—C5—C6173.3 (3)C4—C5—C6—C7177.1 (3)
Cl2—C2—C1—O16.2 (4)C6—C7—N1—C8177.4 (4)
Cl2—C2—C1—C6178.4 (2)C7—N1—C8—C923.0 (6)
Cl2—C2—C3—C4178.4 (2)C7—N1—C8—C10104.1 (4)
Cl3—C19—C18—C17177.3 (3)C8—C10—C11—C12179.2 (3)
Cl3—C19—C20—C21177.2 (3)C8—C10—C15—C14179.2 (3)
Cl4—C17—C16—O26.4 (5)C9—C8—C10—C1185.4 (4)
Cl4—C17—C16—C21177.8 (3)C9—C8—C10—C1593.8 (4)
Cl4—C17—C18—C19177.8 (3)C10—C11—C12—C130.0 (6)
O1—Cu1—O2—C16123.0 (3)C10—C15—C14—C130.0 (5)
O1—Cu1—N1—C725.3 (4)C11—C10—C15—C140.0 (5)
O1—Cu1—N1—C8163.9 (3)C11—C12—C13—C140.0 (6)
O1—Cu1—N2—C22168.8 (4)C12—C11—C10—C150.0 (5)
O1—Cu1—N2—C2317.7 (3)C12—C13—C14—C150.0 (6)
O1—C1—C2—C3175.4 (3)C16—C17—C18—C190.0 (5)
O1—C1—C6—C5175.1 (3)C16—C21—C20—C190.0 (5)
O1—C1—C6—C77.9 (5)C17—C16—C21—C200.0 (5)
O2—Cu1—O1—C1136.1 (3)C17—C16—C21—C22171.6 (4)
O2—Cu1—N1—C7176.8 (4)C17—C18—C19—C200.0 (5)
O2—Cu1—N1—C812.3 (3)C18—C17—C16—C210.0 (5)
O2—Cu1—N2—C2215.9 (4)C18—C19—C20—C210.0 (5)
O2—Cu1—N2—C23170.7 (3)C19—C20—C21—C22172.2 (3)
O2—C16—C17—C18175.9 (3)C21—C22—N2—C23176.7 (4)
O2—C16—C21—C20175.6 (3)C22—N2—C23—C2418.9 (6)
O2—C16—C21—C2212.8 (5)C22—N2—C23—C25108.0 (4)
N1—Cu1—O1—C133.2 (3)C23—C25—C26—C27178.1 (4)
N1—Cu1—O2—C16134.7 (3)C23—C25—C30—C29178.0 (4)
N1—Cu1—N2—C2287.3 (4)C24—C23—C25—C2671.2 (5)
N1—Cu1—N2—C2386.2 (4)C24—C23—C25—C30110.8 (4)
N1—C7—C6—C115.6 (7)C25—C26—C27—C280.0 (6)
N1—C7—C6—C5167.3 (4)C25—C30—C29—C280.0 (8)
N1—C8—C10—C11145.8 (3)C26—C25—C30—C290.0 (6)
N1—C8—C10—C1535.0 (5)C26—C27—C28—C290.0 (8)
N2—Cu1—O1—C1112.7 (3)C27—C26—C25—C300.0 (6)
N2—Cu1—O2—C1610.9 (3)C27—C28—C29—C300.0 (8)
N2—Cu1—N1—C780.3 (4)C27—C28—C29—C300.0 (8)
N2—Cu1—N1—C890.6 (4)
(II) bis[(R)-3-ethoxy-N-(1-phenylethyl)salicylideneaminato-κ2N,O)]copper(II) top
Crystal data top
[Cu(C17H18NO2)2]F(000) = 1260.0
Mr = 600.20Dx = 1.306 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 9.227 (4) Åθ = 10.5–12.0°
b = 42.38 (1) ŵ = 0.76 mm1
c = 8.035 (3) ÅT = 298 K
β = 103.67 (3)°Plate, brown
V = 3053.0 (19) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.161
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 411
Tmin = 0.762, Tmax = 0.860k = 055
7924 measured reflectionsl = 1010
7100 independent reflections3 standard reflections every 150 reflections
3976 reflections with I > 2σ(I) intensity decay: 0.8%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.1162P)2 + 4.3366P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.066(Δ/σ)max < 0.001
wR(F2) = 0.242Δρmax = 0.69 e Å3
S = 1.02Δρmin = 0.77 e Å3
3976 reflectionsAbsolute structure: Flack (1983), ? Friedel pairs
644 parametersAbsolute structure parameter: 0.04 (3)
H-atom parameters constrained
Crystal data top
[Cu(C17H18NO2)2]V = 3053.0 (19) Å3
Mr = 600.20Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.227 (4) ŵ = 0.76 mm1
b = 42.38 (1) ÅT = 298 K
c = 8.035 (3) Å0.40 × 0.30 × 0.20 mm
β = 103.67 (3)°
Data collection top
Rigaku AFC-7R
diffractometer
3976 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.161
Tmin = 0.762, Tmax = 0.8603 standard reflections every 150 reflections
7924 measured reflections intensity decay: 0.8%
7100 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.242Δρmax = 0.69 e Å3
S = 1.02Δρmin = 0.77 e Å3
3976 reflectionsAbsolute structure: Flack (1983), ? Friedel pairs
644 parametersAbsolute structure parameter: 0.04 (3)
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.0807 (1)0.81450 (3)0.0383 (2)0.0534 (4)
Cu20.0532 (1)1.05037 (3)0.5388 (2)0.0533 (4)
O10.0208 (9)0.7768 (2)0.162 (1)0.061 (2)
O20.0643 (9)0.8591 (2)0.022 (1)0.069 (2)
O30.041 (1)0.7339 (3)0.393 (1)0.077 (3)
O40.0195 (10)0.9156 (2)0.005 (1)0.063 (2)
O50.0047 (9)1.0857 (2)0.685 (1)0.064 (2)
O60.0267 (9)1.0064 (2)0.517 (1)0.057 (2)
O70.052 (1)1.1277 (3)0.927 (1)0.081 (3)
O80.0618 (9)0.9481 (2)0.481 (1)0.063 (2)
N10.057 (1)0.8086 (2)0.115 (1)0.052 (2)
N20.2808 (10)0.8159 (3)0.088 (1)0.057 (2)
N30.053 (1)1.0655 (2)0.367 (1)0.055 (2)
N40.239 (1)1.0463 (2)0.617 (1)0.055 (2)
C10.178 (1)0.7617 (3)0.033 (1)0.049 (2)
C20.296 (1)0.7405 (3)0.037 (2)0.057 (3)
C30.332 (1)0.7177 (3)0.163 (2)0.060 (3)
C40.249 (1)0.7153 (3)0.285 (2)0.063 (3)
C50.131 (1)0.7358 (3)0.283 (2)0.056 (3)
C60.094 (1)0.7580 (3)0.156 (1)0.050 (2)
C70.154 (1)0.7857 (3)0.097 (1)0.048 (2)
C80.043 (1)0.8313 (3)0.257 (1)0.057 (3)
C90.100 (1)0.8254 (4)0.387 (2)0.088 (4)
C100.178 (1)0.8343 (3)0.334 (1)0.057 (3)
C110.294 (1)0.8542 (3)0.259 (1)0.061 (3)
C120.419 (2)0.8584 (4)0.329 (2)0.080 (4)
C130.422 (2)0.8437 (5)0.477 (2)0.094 (5)
C140.313 (2)0.8235 (4)0.550 (2)0.084 (4)
C150.188 (1)0.8176 (4)0.484 (2)0.076 (3)
C160.293 (1)0.8739 (3)0.095 (2)0.055 (3)
C170.387 (1)0.8996 (3)0.118 (2)0.067 (3)
C180.340 (2)0.9297 (3)0.106 (2)0.074 (4)
C190.204 (1)0.9368 (3)0.069 (2)0.062 (3)
C200.114 (1)0.9120 (3)0.040 (1)0.054 (3)
C210.156 (1)0.8803 (3)0.051 (1)0.049 (2)
C220.347 (1)0.8429 (3)0.105 (2)0.060 (3)
C230.366 (1)0.7875 (3)0.107 (2)0.056 (3)
C240.316 (1)0.7728 (3)0.284 (1)0.075 (4)
C250.368 (1)0.7651 (3)0.040 (2)0.053 (3)
C260.445 (1)0.7733 (3)0.205 (2)0.064 (3)
C270.464 (2)0.7529 (4)0.341 (2)0.076 (4)
C280.408 (2)0.7236 (4)0.315 (2)0.083 (4)
C290.329 (2)0.7140 (3)0.155 (2)0.082 (4)
C300.308 (1)0.7348 (3)0.019 (2)0.065 (3)
C310.082 (2)0.7140 (4)0.538 (2)0.081 (4)
C320.041 (2)0.7163 (4)0.634 (2)0.095 (5)
C330.071 (1)0.9470 (3)0.021 (1)0.065 (3)
C340.220 (2)0.9444 (3)0.067 (2)0.074 (4)
C350.185 (1)1.1083 (3)0.549 (2)0.056 (3)
C360.297 (1)1.1311 (3)0.557 (2)0.066 (3)
C370.334 (1)1.1519 (3)0.693 (2)0.066 (3)
C380.253 (1)1.1509 (3)0.822 (2)0.062 (3)
C390.142 (1)1.1294 (3)0.811 (2)0.059 (3)
C400.106 (1)1.1057 (3)0.679 (1)0.052 (3)
C410.149 (1)1.0885 (3)0.402 (2)0.054 (3)
C420.030 (1)1.0520 (3)0.187 (1)0.060 (3)
C430.110 (1)1.0328 (4)0.143 (2)0.091 (5)
C440.167 (1)1.0344 (3)0.168 (1)0.056 (3)
C450.220 (2)1.0392 (4)0.024 (2)0.092 (5)
C460.344 (3)1.0231 (5)0.001 (3)0.114 (7)
C470.420 (2)1.0031 (5)0.128 (3)0.106 (6)
C480.365 (2)0.9971 (4)0.267 (2)0.093 (5)
C490.239 (2)1.0122 (3)0.289 (2)0.072 (3)
C500.248 (1)0.9890 (3)0.594 (1)0.055 (3)
C510.338 (1)0.9627 (3)0.620 (2)0.068 (3)
C520.294 (1)0.9324 (3)0.599 (2)0.070 (3)
C530.160 (1)0.9277 (3)0.552 (2)0.063 (3)
C540.070 (1)0.9519 (3)0.527 (1)0.050 (3)
C550.113 (1)0.9829 (2)0.547 (1)0.051 (2)
C560.303 (1)1.0190 (3)0.626 (2)0.059 (3)
C570.306 (1)1.0759 (3)0.661 (2)0.059 (3)
C580.437 (2)1.0721 (3)0.745 (2)0.083 (4)
C590.351 (1)1.0961 (3)0.502 (2)0.059 (3)
C600.305 (1)1.1272 (3)0.507 (2)0.069 (3)
C610.353 (2)1.1466 (3)0.362 (2)0.086 (4)
C620.440 (2)1.1355 (4)0.214 (2)0.078 (4)
C630.484 (2)1.1045 (4)0.207 (2)0.077 (4)
C640.438 (1)1.0848 (3)0.349 (2)0.063 (3)
C650.110 (2)0.9164 (3)0.462 (2)0.065 (3)
C660.259 (2)0.9185 (3)0.417 (2)0.087 (4)
C670.063 (2)1.1520 (3)1.050 (2)0.077 (4)
C680.065 (2)1.1482 (4)1.132 (2)0.095 (5)
H10.35250.74190.04720.0694*
H20.41270.70370.16530.0722*
H30.27250.69930.37110.0765*
H40.21350.78470.17810.0582*
H50.03100.85140.20970.0689*
H60.09400.80540.43980.1069*
H70.18030.82520.33250.1069*
H80.11460.84140.47170.1069*
H90.28840.86540.15790.0734*
H100.49990.87140.27250.0964*
H110.50230.84760.52900.1141*
H120.32020.81290.65200.1017*
H130.11250.80290.53670.0922*
H140.48120.89570.14220.0816*
H150.40280.94660.12220.0900*
H160.17250.95800.06410.0755*
H170.44380.84130.12650.0719*
H180.46620.79410.09600.0682*
H190.21520.76560.30020.0908*
H200.32110.78790.36870.0908*
H210.37790.75530.29280.0908*
H220.48560.79410.22440.0773*
H230.51780.75930.45250.0914*
H240.42320.70920.40830.0998*
H250.28830.69310.13860.0993*
H260.25170.72840.09100.0795*
H270.09090.69280.50210.0973*
H280.17390.72060.60890.0973*
H290.13260.70940.56070.1136*
H300.01710.70340.73220.1136*
H310.05060.73760.66580.1136*
H320.00180.95790.10930.0782*
H330.08140.95800.08370.0782*
H340.25640.96500.08050.0897*
H350.28800.93370.02150.0897*
H360.20830.93310.17140.0897*
H370.34861.13220.46650.0800*
H380.41291.16670.70000.0806*
H390.27581.16510.91610.0750*
H400.20331.09260.31660.0650*
H410.01671.06940.10990.0730*
H420.19201.04540.15390.1081*
H430.12511.02540.02870.1081*
H440.10041.01530.21890.1081*
H450.16991.05390.06100.1101*
H460.37711.02580.10150.1354*
H470.51090.99370.11790.1272*
H480.41470.98220.35100.1122*
H490.19981.00760.38660.0877*
H500.42910.96640.65190.0830*
H510.35350.91490.61790.0845*
H520.13020.90660.53600.0767*
H530.39631.01940.65710.0723*
H540.22991.08700.73970.0718*
H550.47251.09250.76770.1007*
H560.51591.06110.66970.1007*
H570.40671.06090.84910.1007*
H580.24141.13540.60870.0829*
H590.32301.16810.36800.1033*
H600.46881.14870.11610.0958*
H610.54801.09640.10510.0935*
H620.46601.06320.34030.0763*
H630.11990.90530.56700.0796*
H640.04110.90590.37380.0796*
H650.29520.89800.40490.1053*
H660.24920.93000.31430.1053*
H670.32800.92920.50760.1053*
H680.15491.14991.13410.0931*
H690.05921.17190.99710.0931*
H700.05931.16421.21720.1149*
H710.15541.15011.04890.1149*
H720.05961.12811.18610.1149*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0516 (7)0.0481 (8)0.0627 (9)0.0010 (6)0.0179 (6)0.0007 (7)
Cu20.0565 (7)0.0449 (7)0.0603 (9)0.0043 (6)0.0175 (6)0.0000 (7)
O10.054 (4)0.065 (5)0.071 (5)0.011 (4)0.025 (4)0.007 (4)
O20.053 (5)0.062 (6)0.099 (7)0.003 (4)0.033 (5)0.008 (5)
O30.077 (6)0.092 (7)0.071 (5)0.020 (5)0.032 (5)0.033 (5)
O40.068 (5)0.050 (5)0.073 (5)0.002 (4)0.022 (4)0.002 (4)
O50.062 (5)0.070 (5)0.065 (5)0.014 (4)0.027 (4)0.017 (4)
O60.061 (4)0.045 (4)0.068 (5)0.006 (3)0.021 (4)0.003 (4)
O70.099 (7)0.071 (6)0.081 (6)0.021 (5)0.038 (5)0.021 (5)
O80.076 (5)0.043 (4)0.071 (5)0.006 (4)0.020 (4)0.003 (4)
N10.057 (5)0.036 (4)0.060 (5)0.005 (4)0.008 (4)0.001 (4)
N20.057 (5)0.059 (5)0.057 (5)0.005 (5)0.015 (4)0.002 (5)
N30.058 (5)0.052 (5)0.056 (6)0.001 (4)0.013 (4)0.002 (4)
N40.063 (5)0.049 (5)0.053 (5)0.008 (4)0.012 (4)0.007 (4)
C10.049 (5)0.040 (5)0.060 (6)0.011 (4)0.018 (5)0.004 (5)
C20.056 (6)0.048 (6)0.067 (7)0.001 (5)0.015 (5)0.006 (5)
C30.050 (6)0.047 (6)0.082 (8)0.009 (5)0.014 (6)0.001 (6)
C40.065 (7)0.061 (8)0.060 (7)0.003 (6)0.009 (6)0.003 (6)
C50.054 (6)0.056 (7)0.057 (6)0.000 (5)0.012 (5)0.007 (5)
C60.045 (5)0.044 (6)0.058 (6)0.001 (4)0.006 (4)0.006 (5)
C70.052 (6)0.042 (5)0.055 (6)0.003 (4)0.020 (5)0.002 (5)
C80.057 (6)0.060 (6)0.059 (6)0.006 (5)0.024 (5)0.003 (5)
C90.068 (8)0.10 (1)0.091 (10)0.021 (7)0.012 (7)0.023 (9)
C100.061 (6)0.047 (6)0.061 (7)0.007 (5)0.010 (5)0.005 (5)
C110.066 (7)0.053 (6)0.063 (7)0.003 (5)0.013 (5)0.002 (5)
C120.066 (8)0.086 (10)0.086 (9)0.011 (7)0.016 (7)0.018 (8)
C130.076 (9)0.11 (1)0.10 (1)0.003 (9)0.035 (9)0.03 (1)
C140.10 (1)0.088 (10)0.072 (8)0.010 (8)0.043 (8)0.004 (7)
C150.087 (8)0.086 (9)0.059 (7)0.002 (8)0.026 (6)0.007 (7)
C160.050 (6)0.060 (7)0.057 (7)0.003 (5)0.015 (5)0.001 (5)
C170.055 (6)0.066 (8)0.083 (9)0.020 (6)0.021 (6)0.006 (7)
C180.075 (8)0.059 (8)0.089 (10)0.015 (6)0.024 (7)0.006 (7)
C190.065 (7)0.051 (7)0.071 (8)0.007 (5)0.016 (6)0.002 (6)
C200.057 (6)0.058 (7)0.047 (6)0.007 (5)0.009 (5)0.005 (5)
C210.061 (6)0.038 (5)0.047 (6)0.001 (4)0.013 (5)0.005 (4)
C220.052 (6)0.070 (8)0.058 (7)0.001 (6)0.015 (5)0.006 (6)
C230.043 (6)0.066 (7)0.063 (7)0.009 (5)0.021 (5)0.007 (6)
C240.086 (9)0.092 (9)0.054 (7)0.029 (7)0.029 (6)0.000 (6)
C250.048 (6)0.049 (6)0.066 (7)0.006 (4)0.022 (5)0.007 (5)
C260.069 (7)0.058 (7)0.068 (8)0.019 (6)0.022 (6)0.003 (6)
C270.091 (9)0.082 (10)0.059 (7)0.013 (7)0.030 (7)0.005 (7)
C280.090 (10)0.076 (9)0.09 (1)0.012 (8)0.037 (8)0.026 (8)
C290.091 (10)0.059 (8)0.10 (1)0.010 (7)0.029 (8)0.008 (8)
C300.065 (7)0.057 (7)0.073 (8)0.001 (5)0.014 (6)0.001 (6)
C310.082 (9)0.09 (1)0.077 (10)0.003 (8)0.024 (7)0.017 (8)
C320.11 (1)0.10 (1)0.07 (1)0.01 (1)0.032 (9)0.028 (9)
C330.073 (8)0.053 (7)0.066 (8)0.014 (6)0.012 (6)0.004 (6)
C340.076 (8)0.070 (8)0.073 (9)0.016 (7)0.013 (7)0.002 (7)
C350.056 (6)0.049 (6)0.064 (7)0.002 (5)0.017 (5)0.007 (5)
C360.053 (6)0.048 (6)0.100 (10)0.000 (5)0.025 (6)0.008 (7)
C370.060 (7)0.040 (6)0.095 (9)0.008 (5)0.010 (6)0.005 (6)
C380.076 (8)0.038 (6)0.071 (8)0.003 (5)0.016 (6)0.001 (5)
C390.066 (7)0.049 (7)0.061 (7)0.004 (5)0.012 (5)0.002 (5)
C400.044 (5)0.049 (6)0.062 (7)0.003 (4)0.012 (5)0.008 (5)
C410.047 (6)0.053 (6)0.066 (7)0.003 (5)0.024 (5)0.004 (5)
C420.076 (7)0.061 (6)0.044 (5)0.006 (6)0.015 (5)0.004 (5)
C430.059 (8)0.14 (1)0.069 (8)0.021 (8)0.003 (6)0.023 (9)
C440.062 (6)0.053 (7)0.057 (7)0.009 (5)0.022 (5)0.004 (5)
C450.12 (1)0.09 (1)0.08 (1)0.013 (9)0.050 (9)0.008 (8)
C460.15 (2)0.08 (1)0.14 (2)0.02 (1)0.10 (2)0.02 (1)
C470.079 (10)0.09 (1)0.17 (2)0.013 (9)0.06 (1)0.04 (1)
C480.062 (8)0.08 (1)0.14 (1)0.001 (7)0.030 (9)0.027 (10)
C490.071 (8)0.059 (7)0.088 (9)0.007 (6)0.023 (7)0.006 (6)
C500.055 (6)0.054 (6)0.054 (6)0.005 (5)0.009 (5)0.002 (5)
C510.066 (7)0.059 (8)0.078 (8)0.014 (6)0.018 (6)0.012 (6)
C520.070 (8)0.051 (7)0.083 (9)0.020 (6)0.009 (7)0.004 (6)
C530.069 (8)0.052 (7)0.066 (8)0.005 (5)0.010 (6)0.003 (6)
C540.057 (7)0.046 (6)0.045 (6)0.000 (5)0.007 (5)0.003 (5)
C550.062 (6)0.026 (5)0.063 (7)0.008 (4)0.010 (5)0.004 (4)
C560.045 (6)0.065 (8)0.067 (7)0.007 (5)0.013 (5)0.009 (6)
C570.065 (7)0.057 (7)0.060 (7)0.009 (5)0.023 (5)0.004 (5)
C580.078 (9)0.089 (10)0.092 (9)0.019 (7)0.039 (8)0.019 (8)
C590.061 (6)0.051 (6)0.069 (7)0.002 (5)0.023 (6)0.001 (5)
C600.076 (8)0.056 (7)0.077 (8)0.003 (6)0.024 (7)0.004 (7)
C610.10 (1)0.057 (8)0.11 (1)0.005 (7)0.031 (9)0.008 (8)
C620.088 (9)0.071 (9)0.083 (9)0.019 (7)0.033 (8)0.005 (7)
C630.090 (9)0.073 (9)0.068 (8)0.014 (7)0.019 (7)0.001 (7)
C640.079 (8)0.046 (6)0.063 (7)0.003 (5)0.013 (6)0.007 (5)
C650.084 (9)0.047 (7)0.063 (7)0.013 (6)0.012 (6)0.001 (5)
C660.10 (1)0.073 (9)0.09 (1)0.027 (8)0.030 (9)0.004 (8)
C670.12 (1)0.048 (7)0.065 (9)0.004 (7)0.019 (8)0.016 (7)
C680.11 (1)0.08 (1)0.10 (1)0.021 (10)0.04 (1)0.007 (10)
Geometric parameters (Å, º) top
Cu1—O11.895 (9)C29—H250.950
Cu1—O21.90 (1)C30—H260.950
Cu1—N11.98 (1)C31—C321.51 (2)
Cu1—N21.980 (10)C31—H270.950
Cu2—O51.899 (9)C31—H280.950
Cu2—O61.891 (8)C32—H290.950
Cu2—N31.98 (1)C32—H300.950
Cu2—N41.97 (1)C32—H310.950
O1—C61.33 (1)C33—C341.51 (2)
O2—C211.29 (1)C33—H320.950
O3—C51.36 (2)C33—H330.950
O3—C311.41 (2)C34—H340.950
O4—C201.37 (2)C34—H350.950
O4—C331.43 (2)C34—H360.950
O5—C401.28 (1)C35—C361.41 (2)
O6—C551.33 (1)C35—C401.40 (2)
O7—C391.39 (2)C35—C411.43 (2)
O7—C671.41 (2)C36—C371.38 (2)
O8—C541.36 (2)C36—H370.950
O8—C651.43 (2)C37—C381.42 (2)
N1—C71.30 (1)C37—H380.950
N1—C81.48 (1)C38—C391.35 (2)
N2—C221.32 (2)C38—H390.950
N2—C231.47 (2)C39—C401.44 (2)
N3—C411.30 (1)C41—H400.950
N3—C421.53 (1)C42—C431.49 (2)
N4—C561.31 (2)C42—C441.51 (2)
N4—C571.48 (2)C42—H410.950
C1—C21.41 (2)C43—H420.950
C1—C61.40 (2)C43—H430.950
C1—C71.44 (2)C43—H440.950
C2—C31.38 (2)C44—C451.37 (2)
C2—H10.950C44—C491.40 (2)
C3—C41.38 (2)C45—C461.39 (3)
C3—H20.950C45—H450.950
C4—C51.39 (2)C46—C471.38 (3)
C4—H30.950C46—H460.950
C5—C61.37 (2)C47—C481.36 (3)
C7—H40.950C47—H470.950
C8—C91.49 (2)C48—C491.38 (2)
C8—C101.52 (2)C48—H480.950
C8—H50.950C49—H490.950
C9—H60.950C50—C511.43 (2)
C9—H70.950C50—C551.41 (2)
C9—H80.950C50—C561.41 (2)
C10—C111.38 (2)C51—C521.37 (2)
C10—C151.42 (2)C51—H500.950
C11—C121.41 (2)C52—C531.39 (2)
C11—H90.950C52—H510.950
C12—C131.34 (2)C53—C541.37 (2)
C12—H100.950C53—H520.950
C13—C141.35 (2)C54—C551.39 (2)
C13—H110.950C56—H530.950
C14—C151.40 (2)C57—C581.53 (2)
C14—H120.950C57—C591.51 (2)
C15—H130.950C57—H540.950
C16—C171.43 (2)C58—H550.950
C16—C211.42 (2)C58—H560.950
C16—C221.41 (2)C58—H570.950
C17—C181.36 (2)C59—C601.38 (2)
C17—H140.950C59—C641.39 (2)
C18—C191.39 (2)C60—C611.41 (2)
C18—H150.950C60—H580.950
C19—C201.39 (2)C61—C621.36 (2)
C19—H160.950C61—H590.950
C20—C211.41 (2)C62—C631.37 (2)
C22—H170.950C62—H600.950
C23—C241.52 (2)C63—C641.39 (2)
C23—C251.51 (2)C63—H610.950
C23—H180.950C64—H620.950
C24—H190.950C65—C661.50 (2)
C24—H200.950C65—H630.950
C24—H210.950C65—H640.950
C25—C261.39 (2)C66—H650.950
C25—C301.39 (2)C66—H660.950
C26—C271.37 (2)C66—H670.950
C26—H220.950C67—C681.49 (2)
C27—C281.34 (2)C67—H680.950
C27—H230.950C67—H690.950
C28—C291.38 (2)C68—H700.950
C28—H240.950C68—H710.950
C29—C301.38 (2)C68—H720.950
O1—Cu1—O2148.9 (3)C31—C32—H31109.4
O1—Cu1—N194.0 (4)H29—C32—H30109.3
O1—Cu1—N295.2 (4)H29—C32—H31109.2
O2—Cu1—N190.5 (4)H30—C32—H31109.9
O2—Cu1—N294.4 (4)O4—C33—C34107 (1)
N1—Cu1—N2153.4 (4)O4—C33—H32110.0
O5—Cu2—O6144.0 (3)O4—C33—H33110.2
O5—Cu2—N393.5 (4)C34—C33—H32110.0
O5—Cu2—N490.6 (4)C34—C33—H33110.0
O6—Cu2—N399.2 (4)H32—C33—H33109.4
O6—Cu2—N494.8 (4)C33—C34—H34109.4
N3—Cu2—N4150.0 (4)C33—C34—H35109.7
Cu1—O1—C6128.3 (8)C33—C34—H36109.4
Cu1—O2—C21127.8 (8)H34—C34—H35109.6
C5—O3—C31119 (1)H34—C34—H36109.1
C20—O4—C33117.7 (10)H35—C34—H36109.7
Cu2—O5—C40127.2 (8)C36—C35—C40121 (1)
Cu2—O6—C55128.7 (8)C36—C35—C41117 (1)
C39—O7—C67118 (1)C40—C35—C41121 (1)
C54—O8—C65117.4 (10)C35—C36—C37120 (1)
Cu1—N1—C7123.3 (8)C35—C36—H37119.5
Cu1—N1—C8116.5 (7)C37—C36—H37119.7
C7—N1—C8120 (1)C36—C37—C38119 (1)
Cu1—N2—C22121.6 (9)C36—C37—H38120.5
Cu1—N2—C23123.0 (8)C38—C37—H38120.3
C22—N2—C23115.4 (10)C37—C38—C39119 (1)
Cu2—N3—C41121.5 (8)C37—C38—H39120.4
Cu2—N3—C42123.8 (7)C39—C38—H39119.9
C41—N3—C42114 (1)O7—C39—C38123 (1)
Cu2—N4—C56122.3 (9)O7—C39—C40112 (1)
Cu2—N4—C57116.6 (8)C38—C39—C40123 (1)
C56—N4—C57121 (1)O5—C40—C35126 (1)
C2—C1—C6117 (1)O5—C40—C39118 (1)
C2—C1—C7117 (1)C35—C40—C39115 (1)
C6—C1—C7125 (1)N3—C41—C35129.4 (12)
C1—C2—C3121 (1)N3—C41—H40115.6
C1—C2—H1119.4C35—C41—H40115.7
C3—C2—H1119.5N3—C42—C43110.7 (10)
C2—C3—C4119 (1)N3—C42—C44110.3 (8)
C2—C3—H2120.2N3—C42—H41107.2
C4—C3—H2120.1C43—C42—C44113 (1)
C3—C4—C5120 (1)C43—C42—H41107.3
C3—C4—H3119.8C44—C42—H41107.3
C5—C4—H3119.8C42—C43—H42109.6
O3—C5—C4123 (1)C42—C43—H43109.7
O3—C5—C6116.4 (10)C42—C43—H44109.3
C4—C5—C6120 (1)H42—C43—H43109.6
O1—C6—C1122.2 (10)H42—C43—H44109.1
O1—C6—C5116 (1)H43—C43—H44109.5
C1—C6—C5121.3 (10)C42—C44—C45118 (1)
N1—C7—C1126 (1)C42—C44—C49122 (1)
N1—C7—H4116.8C45—C44—C49118 (1)
C1—C7—H4117.0C44—C45—C46120 (1)
N1—C8—C9109.6 (10)C44—C45—H45119.5
N1—C8—C10115.9 (9)C46—C45—H45119.8
N1—C8—H5105.7C45—C46—C47119 (2)
C9—C8—C10113 (1)C45—C46—H46120.0
C9—C8—H5105.5C47—C46—H46120.3
C10—C8—H5105.6C46—C47—C48119 (1)
C8—C9—H6109.2C46—C47—H47120.0
C8—C9—H7109.5C48—C47—H47120.1
C8—C9—H8109.7C47—C48—C49121 (1)
H6—C9—H7109.2C47—C48—H48119.6
H6—C9—H8109.4C49—C48—H48119.3
H7—C9—H8109.7C44—C49—C48119 (1)
C8—C10—C11119 (1)C44—C49—H49119.9
C8—C10—C15121 (1)C48—C49—H49120.6
C11—C10—C15118 (1)C51—C50—C55118 (1)
C10—C11—C12121 (1)C51—C50—C56115 (1)
C10—C11—H9119.1C55—C50—C56126 (1)
C12—C11—H9119.3C50—C51—C52121 (1)
C11—C12—C13118 (1)C50—C51—H50119.2
C11—C12—H10120.4C52—C51—H50119.5
C13—C12—H10120.7C51—C52—C53118 (1)
C12—C13—C14120 (1)C51—C52—H51120.9
C12—C13—H11119.3C53—C52—H51120.9
C14—C13—H11120.0C52—C53—C54122 (1)
C13—C14—C15122 (1)C52—C53—H52118.4
C13—C14—H12118.5C54—C53—H52118.6
C15—C14—H12118.5O8—C54—C53124 (1)
C10—C15—C14117 (1)O8—C54—C55116 (1)
C10—C15—H13121.5C53—C54—C55119 (1)
C14—C15—H13121.4O6—C55—C50120.8 (10)
C17—C16—C21119 (1)O6—C55—C54119 (1)
C17—C16—C22117 (1)C50—C55—C54120 (1)
C21—C16—C22122 (1)N4—C56—C50126 (1)
C16—C17—C18119 (1)N4—C56—H53116.7
C16—C17—H14120.3C50—C56—H53116.5
C18—C17—H14120.1N4—C57—C58116 (1)
C17—C18—C19122 (1)N4—C57—C59109 (1)
C17—C18—H15118.8N4—C57—H54106.9
C19—C18—H15118.8C58—C57—C59110 (1)
C18—C19—C20118 (1)C58—C57—H54107.0
C18—C19—H16120.7C59—C57—H54106.9
C20—C19—H16120.7C57—C58—H55109.4
O4—C20—C19124 (1)C57—C58—H56109.5
O4—C20—C21113 (1)C57—C58—H57109.8
C19—C20—C21121 (1)H55—C58—H56109.1
O2—C21—C16124 (1)H55—C58—H57109.4
O2—C21—C20117 (1)H56—C58—H57109.7
C16—C21—C20118 (1)C57—C59—C60119 (1)
N2—C22—C16128 (1)C57—C59—C64122 (1)
N2—C22—H17115.7C60—C59—C64117 (1)
C16—C22—H17115.9C59—C60—C61119 (1)
N2—C23—C24112.5 (9)C59—C60—H58119.8
N2—C23—C25110 (1)C61—C60—H58120.3
N2—C23—H18106.4C60—C61—C62121 (1)
C24—C23—C25114 (1)C60—C61—H59119.3
C24—C23—H18106.3C62—C61—H59118.9
C25—C23—H18106.5C61—C62—C63118 (1)
C23—C24—H19109.4C61—C62—H60121.0
C23—C24—H20109.8C63—C62—H60120.6
C23—C24—H21109.5C62—C63—C64120 (1)
H19—C24—H20109.4C62—C63—H61119.7
H19—C24—H21109.1C64—C63—H61119.5
H20—C24—H21109.6C59—C64—C63121 (1)
C23—C25—C26119.6 (10)C59—C64—H62119.3
C23—C25—C30123 (1)C63—C64—H62119.4
C26—C25—C30116 (1)O8—C65—C66107 (1)
C25—C26—C27122 (1)O8—C65—H63109.9
C25—C26—H22118.7O8—C65—H64110.1
C27—C26—H22118.5C66—C65—H63110.2
C26—C27—C28118 (1)C66—C65—H64109.8
C26—C27—H23120.6H63—C65—H64109.7
C28—C27—H23120.6C65—C66—H65109.7
C27—C28—C29121 (1)C65—C66—H66109.9
C27—C28—H24119.3C65—C66—H67109.1
C29—C28—H24119.4H65—C66—H66110.1
C28—C29—C30119 (1)H65—C66—H67108.9
C28—C29—H25120.3H66—C66—H67109.2
C30—C29—H25120.2O7—C67—C68107 (1)
C25—C30—C29120 (1)O7—C67—H68109.3
C25—C30—H26119.2O7—C67—H69110.2
C29—C30—H26119.8C68—C67—H68110.1
O3—C31—C32107 (1)C68—C67—H69110.3
O3—C31—H27109.8H68—C67—H69109.4
O3—C31—H28110.4C67—C68—H70109.1
C32—C31—H27110.0C67—C68—H71109.8
C32—C31—H28110.3C67—C68—H72109.5
H27—C31—H28109.2H70—C68—H71109.7
C31—C32—H29109.4H70—C68—H72108.7
C31—C32—H30109.7H71—C68—H72109.9
Cu1—O1—C6—C19 (1)C1—C6—C5—C43 (1)
Cu1—O1—C6—C5167.1 (8)C1—C7—N1—C8178.9 (9)
Cu1—O2—C21—C162 (1)C2—C1—C6—C54 (1)
Cu1—O2—C21—C20176.3 (7)C2—C3—C4—C50 (1)
Cu1—N1—C7—C10 (1)C3—C2—C1—C62 (1)
Cu1—N1—C8—C970 (1)C3—C2—C1—C7176 (1)
Cu1—N1—C8—C10159.3 (7)C3—C4—C5—C61 (1)
Cu1—N2—C22—C161 (1)C4—C5—O3—C3111 (1)
Cu1—N2—C23—C2480 (1)C5—O3—C31—C32178 (1)
Cu1—N2—C23—C2548 (1)C5—C6—C1—C7175 (1)
Cu2—O5—C40—C358 (1)C6—C5—O3—C31172 (1)
Cu2—O5—C40—C39174.7 (7)C7—N1—C8—C9108.2 (11)
Cu2—O6—C55—C503 (1)C7—N1—C8—C1022 (1)
Cu2—O6—C55—C54178.3 (7)C8—C10—C11—C12178 (1)
Cu2—N3—C41—C356 (1)C8—C10—C15—C14176 (1)
Cu2—N3—C42—C4315 (1)C9—C8—C10—C11147 (1)
Cu2—N3—C42—C44111.3 (10)C9—C8—C10—C1531 (1)
Cu2—N4—C56—C504 (1)C10—C11—C12—C132 (2)
Cu2—N4—C57—C58171.8 (7)C10—C15—C14—C131 (2)
Cu2—N4—C57—C5963.4 (10)C11—C10—C15—C142 (1)
O1—Cu1—O2—C21102 (1)C11—C12—C13—C144 (2)
O1—Cu1—N1—C74.8 (9)C12—C11—C10—C150 (1)
O1—Cu1—N1—C8173.3 (7)C12—C13—C14—C152 (2)
O1—Cu1—N2—C22147.4 (9)C16—C17—C18—C190 (2)
O1—Cu1—N2—C2333.1 (8)C16—C21—C20—C190 (1)
O1—C6—C1—C2179.8 (10)C16—C22—N2—C23179 (1)
O1—C6—C1—C70 (1)C17—C16—C21—C203 (1)
O1—C6—C5—O34 (1)C17—C18—C19—C201 (2)
O1—C6—C5—C4179 (1)C18—C17—C16—C213 (1)
O2—Cu1—O1—C687 (1)C18—C17—C16—C22178 (1)
O2—Cu1—N1—C7144.4 (8)C18—C19—C20—C211 (1)
O2—Cu1—N1—C837.5 (7)C19—C20—O4—C330 (1)
O2—Cu1—N2—C223.0 (9)C20—O4—C33—C34178.5 (9)
O2—Cu1—N2—C23176.6 (8)C20—C21—C16—C22178 (1)
O2—C21—C16—C17177 (1)C21—C20—O4—C33179.6 (9)
O2—C21—C16—C222 (1)C22—N2—C23—C2499 (1)
O2—C21—C20—O41 (1)C22—N2—C23—C25131.2 (10)
O2—C21—C20—C19179 (1)C23—C25—C26—C27172 (1)
O3—C5—C4—C3176 (1)C23—C25—C30—C29171 (1)
O3—C5—C6—C1179.1 (10)C24—C23—C25—C26164 (1)
O4—C20—C19—C18176 (1)C24—C23—C25—C309 (1)
O4—C20—C21—C16179.4 (9)C25—C26—C27—C280 (2)
O5—Cu2—O6—C5598.4 (10)C25—C30—C29—C281 (2)
O5—Cu2—N3—C4113.0 (9)C26—C25—C30—C292 (1)
O5—Cu2—N3—C42166.2 (8)C26—C27—C28—C291 (2)
O5—Cu2—N4—C56148.8 (9)C27—C26—C25—C301 (1)
O5—Cu2—N4—C5733.5 (7)C27—C28—C29—C300 (2)
O5—C40—C35—C36178 (1)C35—C36—C37—C382 (1)
O5—C40—C35—C413 (1)C35—C40—C39—C386 (1)
O5—C40—C39—O72 (1)C35—C41—N3—C42172 (1)
O5—C40—C39—C38176 (1)C36—C35—C40—C394 (1)
O6—Cu2—O5—C4096 (1)C36—C37—C38—C390 (1)
O6—Cu2—N3—C41133.2 (9)C37—C36—C35—C400 (1)
O6—Cu2—N3—C4247.6 (8)C37—C36—C35—C41177 (1)
O6—Cu2—N4—C564.5 (9)C37—C38—C39—C403 (1)
O6—Cu2—N4—C57177.8 (7)C38—C39—O7—C678 (1)
O6—C55—C50—C51178 (1)C39—O7—C67—C68168 (1)
O6—C55—C50—C564 (1)C39—C40—C35—C41173 (1)
O6—C55—C54—O81 (1)C40—C39—O7—C67172.1 (10)
O6—C55—C54—C53178.0 (10)C41—N3—C42—C43163 (1)
O7—C39—C38—C37176 (1)C41—N3—C42—C4469 (1)
O7—C39—C40—C35174.3 (10)C42—C44—C45—C46179 (1)
O8—C54—C53—C52179 (1)C42—C44—C49—C48179 (1)
O8—C54—C55—C50179.6 (9)C43—C42—C44—C45100 (1)
N1—Cu1—O1—C69.9 (9)C43—C42—C44—C4976 (1)
N1—Cu1—O2—C21158.8 (9)C44—C45—C46—C472 (2)
N1—Cu1—N2—C22102 (1)C44—C49—C48—C470 (2)
N1—Cu1—N2—C2376 (1)C45—C44—C49—C483 (1)
N1—C7—C1—C2175 (1)C45—C46—C47—C485 (2)
N1—C7—C1—C64 (1)C46—C45—C44—C491 (2)
N1—C8—C10—C1184 (1)C46—C47—C48—C493 (2)
N1—C8—C10—C1596 (1)C50—C51—C52—C530 (1)
N2—Cu1—O1—C6164.9 (9)C50—C55—C54—C530 (1)
N2—Cu1—O2—C215.0 (9)C50—C56—N4—C57177 (1)
N2—Cu1—N1—C7114 (1)C51—C50—C55—C540 (1)
N2—Cu1—N1—C863 (1)C51—C52—C53—C540 (1)
N2—C22—C16—C17179.9 (14)C52—C51—C50—C550 (1)
N2—C22—C16—C215 (1)C52—C51—C50—C56177 (1)
N2—C23—C25—C2667 (1)C52—C53—C54—C550 (1)
N2—C23—C25—C30118 (1)C53—C54—O8—C651 (1)
N3—Cu2—O5—C4014.4 (9)C54—O8—C65—C66178.1 (9)
N3—Cu2—O6—C55152.6 (9)C54—C55—C50—C56177.1 (10)
N3—Cu2—N4—C56113 (1)C55—C54—O8—C65178.8 (9)
N3—Cu2—N4—C5764 (1)C56—N4—C57—C5810 (1)
N3—C41—C35—C36178 (1)C56—N4—C57—C59114 (1)
N3—C41—C35—C403 (1)C57—C59—C60—C61176 (1)
N3—C42—C44—C45134 (1)C57—C59—C64—C63176 (1)
N3—C42—C44—C4948 (1)C58—C57—C59—C60103.3 (12)
N4—Cu2—O5—C40164.6 (9)C58—C57—C59—C6476 (1)
N4—Cu2—O6—C550.7 (9)C59—C60—C61—C621 (2)
N4—Cu2—N3—C41110.2 (10)C59—C64—C63—C622 (2)
N4—Cu2—N3—C4269 (1)C60—C59—C64—C633 (2)
N4—C56—C50—C51177 (1)C60—C61—C62—C631 (2)
N4—C56—C50—C550 (1)C61—C60—C59—C642 (2)
N4—C57—C59—C60128 (1)C61—C62—C63—C641 (2)
N4—C57—C59—C6451 (1)C61—C62—C63—C641 (2)
C1—C2—C3—C40 (1)

Experimental details

(I)(II)
Crystal data
Chemical formula[Cu(C15H12Cl2NO)2][Cu(C17H18NO2)2]
Mr649.86600.20
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)297298
a, b, c (Å)11.166 (5), 14.852 (7), 8.636 (4)9.227 (4), 42.38 (1), 8.035 (3)
β (°) 97.89 (4) 103.67 (3)
V3)1418.6 (11)3053.0 (19)
Z24
Radiation typeMo KαMo Kα
µ (mm1)1.180.76
Crystal size (mm)0.30 × 0.30 × 0.200.40 × 0.30 × 0.20
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Rigaku AFC-7R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
ψ scan
(North et al., 1968)
Tmin, Tmax0.709, 0.7900.762, 0.860
No. of measured, independent and
observed [I > 2σ(I)] reflections
3771, 3387, 2958 7924, 7100, 3976
Rint0.0200.161
(sin θ/λ)max1)0.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.093, 1.05 0.066, 0.242, 1.02
No. of reflections29583976
No. of parameters304644
No. of restraints??
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.500.69, 0.77
Absolute structureFlack (1983), 3387 Friedel pairsFlack (1983), ? Friedel pairs
Absolute structure parameter0.01 (2)0.04 (3)

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), WinAFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 2001), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) for (I) top
Cu1—O11.890 (3)Cu1—N21.984 (4)
Cu1—O21.878 (3)N1—C71.275 (6)
Cu1—N11.995 (4)N2—C221.280 (5)
O1—Cu1—O2150.9 (1)O2—Cu1—N194.6 (1)
O1—Cu1—N191.9 (1)O2—Cu1—N293.6 (1)
O1—Cu1—N297.3 (1)N1—Cu1—N2144.7 (2)
C7—N1—C8—C10104.1 (4)C22—N2—C23—C25108.0 (4)
Selected geometric parameters (Å, º) for (II) top
Cu1—O11.895 (9)Cu2—N31.98 (1)
Cu1—O21.90 (1)Cu2—N41.97 (1)
Cu1—N11.98 (1)N1—C71.30 (1)
Cu1—N21.980 (10)N2—C221.32 (2)
Cu2—O51.899 (9)N3—C411.30 (1)
Cu2—O61.891 (8)N4—C561.31 (2)
O1—Cu1—O2148.9 (3)O5—Cu2—O6144.0 (3)
O1—Cu1—N194.0 (4)O5—Cu2—N393.5 (4)
O1—Cu1—N295.2 (4)O5—Cu2—N490.6 (4)
O2—Cu1—N190.5 (4)O6—Cu2—N399.2 (4)
O2—Cu1—N294.4 (4)O6—Cu2—N494.8 (4)
N1—Cu1—N2153.4 (4)N3—Cu2—N4150.0 (4)
C7—N1—C8—C1022 (1)C41—N3—C42—C4469 (1)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds