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The crystal structures of the title compounds, [Cu(C15H11N2O2)2(C14H15N)2] and [Cu(C15H11N2O2)2(C14H15N)2]·2CHCl3, respectively, have been determined. The red disolvate complex affords a square-planar CuN4 coordination environment in which the CuII atom lies on a centre of symmetry. The blue solvent-free complex affords a distorted square-pyramidal CuN4O coordination environment and adjacent mol­ecules form centrosymmetric dimers. A comparison of the different crystal structures focuses on the role of the solvent mol­ecules in supramolecular assemblies of the copper(II) complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010500209X/ta1482sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010500209X/ta1482Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010500209X/ta1482IIsup3.hkl
Contains datablock II

CCDC references: 269013; 269014

Comment top

In recent years, studies of supramolecular self-assembling metal–organic frameworks of metal complexes have been extensively carried out, with the aim of rational construction of desired crystal structures and fine-tuning of their functions (Eddaoudi et al., 2001; Evans et al., 2002; Yaghi et al., 1998). In particular, host–guest inclusion of small molecules and hydrogen-bonded flexible self-assemblies enable the realisation of appropriate crystal packing containing guest molecules (Holman et al., 2001), which depends on the novelty of the secondary building units as a synthon. In this respect, for example, vapochromic switching of optoelectronic properties may be one of the most promising strategies for the preparation of functional materials (Kato et al., 2002; Fernandez et al., 2003). It is well known that copper(II) complexes exhibit a remarkable variety in their coordination geometries and corresponding optoelectronic properties. Some copper(II) complexes incorporating monodentate 5,5-diphenylhydantoinate ligands have been studied previously. In the solid state, most of the related complexes afford a four-coordinated square-planar CuN4 coordination geometry (Akitsu, Komorita & Urushiyama, 2001) with the aid of crystal-packing forces. Appropriate steric factors of the ligands can lead to a tetrahedrally distorted square-planar CuN4 coordination geometry (Akitsu et al., 2003) or a five-coordinated square-pyramidal CuN4O coordination geometry (Akitsu et al., 1997). To date, structural regulation by other means, such as solvent in the crystal (Tynan et al., 2004), has not been observed for analogous complexes. We report here a structural comparison of trans-bis(2,2-diphenylethylamine)bis(5,5-diphenylhydantoinato)copper(II)chloroform disolvate, (I), and dimeric trans-bis(2,2-diphenylethylamine)bis(5,5-diphenylhydantoinato)copper(II), (II).

Complex (I), the chloroform disolvate, affords a square-planar CuN4 coordination geometry, in which the Cu atom lies on an inversion centre (Fig. 1). Both the neutral 2,2-diphenylethylamine ligands and the anionic deprotonated 5,5-diphenylhydantoinate ligands act as monodentate ligands with N-atom donors, and they are coordinated on trans sites with respect to the Cu atom. The Cu—N bond distances (Table 1) are within the range found in related complexes, some of which are planar and some of which exhibit some tetrahedral distortion, viz. the Cu—N(imide) distances range from 1.975 (5) to 2.05 (1) Å, whereas the Cu—N(amine) distances range from 1.97 (1) to 2.030 (4) Å (Akitsu, Komorita & Kushi, 2001; Akitsu et al., 2003; Akitsu & Einaga, 2004). The cis-N1—Cu1—N3 angles are close to right angles. The dihedral angle between the Cu1/N1/N3/N1i/N3i mean plane of the coordination sphere and the N1/C1/N2/C2/C3 plane of the ligands is 139.4 (1)°, and those between the five-membered C3/C2/N1/C1/N2 ring of the 5,5-diphenylhydantoinate ligand and the connecting phenyl groups, i.e. C4/C5/C6/C7/C8/C9 and C10/C11/C12/C13/C14/C15, are 57.7 (1) and 123.0 (1)°, respectively [symmetry code: (i) 1 − x, 1 − y, 1 − z].

The solvent-free complex, (II), affords a slightly distorted pyramidal CuN4 coordination geometry (Fig. 2) and adjacent molecules form centrosymmetric dimers, with Cu1—O3iii 2.397 (4) Å [symmetry code: (iii) 2 − x, 1 − y, 1 − z] (Fig. 3). The Cu—N bond distances are also within the range found in related complexes (Table 3). The dihedral angle between the N1/Cu1/N3 and N4/Cu1/N6 planes is 16.69 (1)°. The Cu atom deviates slightly from the N1/N3/N4/N6 plane, by 0.178 (2) Å. The dihedral angle between the Cu1/N1/N3/N4/N6 and N1/C1/N2/C2/C3 planes is 94.7 (2)°, while that between the Cu1/N1/N3/N4/N6 and N4/C30/N5/C31/C32 planes is 35.2 (2)°. Although the planarity of the coordination environment is broken, the sp2 character of the N-donor atoms of the 5,5-diphenylhydantoinate ligands is still maintained; the C1—N1—C3 and C30—N4—C31 bond angles are 108.0 (5) and 106.2 (5)°, respectively.

To the best of our knowledge, this is the first case of related complexes which exhibit different coordination geometries in the presence or absence of solvent molecules in the crystal. In the crystal structure of (I), four intramolecular hydrogen bonds are formed around the coordination sphere, i.e. N3—H13···O2 and N3—H12···O1i (Table 2). Furthermore, adjacent molecules are linked by double complementary intermolecular N2—H1···O1ii hydrogen bonds along the crystallographic b axis [N···O 2.900 (3) Å; symmetry code: (ii) 1 − x, 1 − y, −z]. The chloroform solvent molecules also play an important role in stabilizing the crystal packing of (I) via a C30—H27···O2 hydrogen bond [C···O 3.507 (5) Å]. On the other hand, the crystal-packing mode of (II) is quite different. Only two intramolecular hydrogen bonds, namely N3—H12···O4 and N6—H39···O3, are formed on one side of the coordination sphere (Table 4). Moreover, intermolecular hydrogen bonds, i.e. N5—H27···O2iii and N2—H1···O4iv, link adjacent molecules to form hydrogen-bonded networks [symmetry codes: (iii) 2 − x, 1 − y, 1 − z; (iv) 2 − x, 1 − y, −z].

Experimental top

Treatment of equimolar quantities of copper(II) acetate (0.454 g, 2.50 mmol), 5,5-diphenylhydantoin (1.26 g, 5.00 mmol) and 2,2-diphenylethylamine (0.99 g, 5.00 mmol) in ethanol (100 ml) at 323 K for 2 h gave rise to crude precipitates. Red–violet plate-like crystals of (I) were obtained from a solution in chloroform–methanol (4:1 v/v) at 298 K over a period of several days. IR (KBr): 1644 cm−1 (amide I band); m.p. 629 K (decomposition). Recrystallization of the crude precipitates from a solution in chloroform–methanol (4:1 v/v) at 283 K overnight yielded only a small amount of blue–violet plate-like crystals of the solvent-free complex, (II). IR (KBr): 1645 cm−1 (amide I band); m.p. 605 K (decomposition).

Refinement top

All H atoms were placed in calculated positions, with C—H = N—H = 0.95 Å, and 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, viz. C4–C9, C10–C15, C18–C23 and C24–C29 for (I), and C4–C9, C10–C15, C18–C23, C24–C29, C33–C38, C39–C44, C47–C52 and C53–C58 for (II), were treated as rigid groups of anisotropic atoms. The intensity of the data was relatively weak, similar to some analogous mononuclear copper complexes with large organic ligands. The largest hole in the difference map of (II) is near atom Cu1, at (0.9919, 0.4909, 0.2953).

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]
[Figure 2]
[Figure 3]
[Figure 4]
Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. Only one chloroform solvent molecule is shown. [Symmetry code: (i) 1 − x, 1 − y, 1 − z].

Fig. 2. The molecular structure of (II) as a monomer, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Fig. 3. The dimeric structure of (II). Displacement ellipsoids are drawn at the 30% probability level. H atoms and phenyl groups have been omitted for clarity. [Symmetry code: (iii) 2 − x, 1 − y, 1 − z].
(I) top
Crystal data top
[Cu(C15H11N2O2)2(C14H15N)2]·2CHCl3F(000) = 2476.0
Mr = 1199.34Dx = 1.393 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 19.37 (1) Åθ = 10.3–12.6°
b = 29.796 (7) ŵ = 0.72 mm1
c = 9.910 (3) ÅT = 298 K
V = 5720 (4) Å3Plate-like, red–violet
Z = 40.41 × 0.16 × 0.10 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.021
ω/2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 1025
Tmin = 0.872, Tmax = 0.931k = 038
8516 measured reflectionsl = 125
6565 independent reflections3 standard reflections every 150 reflections
3338 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.163(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.43 e Å3
3338 reflectionsΔρmin = 0.46 e Å3
302 parameters
Crystal data top
[Cu(C15H11N2O2)2(C14H15N)2]·2CHCl3V = 5720 (4) Å3
Mr = 1199.34Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 19.37 (1) ŵ = 0.72 mm1
b = 29.796 (7) ÅT = 298 K
c = 9.910 (3) Å0.41 × 0.16 × 0.10 mm
Data collection top
Rigaku AFC-7R
diffractometer
3338 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.021
Tmin = 0.872, Tmax = 0.9313 standard reflections every 150 reflections
8516 measured reflections intensity decay: 0.2%
6565 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050302 parameters
wR(F2) = 0.163H-atom parameters constrained
S = 0.99Δρmax = 0.43 e Å3
3338 reflectionsΔρmin = 0.46 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.50000.50000.50000.0307 (1)
Cl10.14371 (8)0.44923 (5)0.42211 (2)0.1146 (6)
Cl20.1733 (1)0.37426 (8)0.5972 (2)0.1334 (7)
Cl30.17950 (7)0.36416 (6)0.3122 (2)0.1019 (5)
O10.5246 (1)0.51803 (8)0.1754 (2)0.0439 (6)
O20.3656 (1)0.43479 (8)0.4037 (2)0.0395 (6)
N10.4545 (1)0.48014 (9)0.3279 (3)0.0318 (6)
N20.4543 (2)0.46060 (9)0.1070 (3)0.0346 (6)
N30.4891 (2)0.43761 (9)0.5727 (3)0.0392 (7)
C10.4814 (2)0.4887 (1)0.1992 (4)0.0334 (8)
C20.4025 (2)0.4493 (1)0.3137 (4)0.0331 (7)
C30.3996 (2)0.4330 (1)0.1652 (3)0.0314 (7)
C40.3313 (1)0.44243 (8)0.0926 (2)0.0375 (8)
C50.2762 (1)0.46458 (9)0.1527 (2)0.055 (1)
C60.2169 (1)0.4736 (1)0.0784 (3)0.074 (1)
C70.2128 (1)0.4605 (1)0.0559 (3)0.075 (2)
C80.2679 (2)0.4383 (1)0.1160 (2)0.067 (1)
C90.3272 (1)0.42931 (9)0.0418 (2)0.051 (1)
C100.4162 (1)0.38285 (5)0.1652 (3)0.0341 (7)
C110.36363 (9)0.35262 (7)0.1946 (3)0.0417 (8)
C120.3778 (1)0.30693 (7)0.2008 (3)0.050 (1)
C130.4444 (1)0.29147 (6)0.1776 (3)0.059 (1)
C140.4970 (1)0.32170 (8)0.1482 (3)0.059 (1)
C150.4828 (1)0.36739 (7)0.1419 (3)0.0480 (10)
C160.5351 (2)0.4026 (1)0.5163 (4)0.0427 (9)
C170.5388 (2)0.3603 (1)0.6065 (4)0.0431 (9)
C180.4681 (1)0.34290 (8)0.6445 (2)0.0387 (8)
C190.4542 (1)0.33384 (9)0.7793 (2)0.053 (1)
C200.3889 (2)0.3193 (1)0.8178 (2)0.066 (1)
C210.3375 (1)0.31388 (9)0.7214 (3)0.066 (1)
C220.3513 (1)0.32295 (9)0.5865 (3)0.061 (1)
C230.4166 (1)0.33746 (9)0.5480 (2)0.0494 (10)
C240.5871 (1)0.32564 (8)0.5414 (3)0.0477 (10)
C250.5617 (1)0.28857 (9)0.4721 (4)0.072 (1)
C260.6071 (2)0.25845 (9)0.4122 (4)0.097 (2)
C270.6779 (2)0.2654 (1)0.4216 (4)0.097 (2)
C280.7033 (1)0.3024 (1)0.4909 (4)0.087 (2)
C290.6579 (1)0.3326 (1)0.5508 (3)0.070 (1)
C300.1934 (2)0.4010 (2)0.4437 (6)0.072 (1)
H10.46900.45890.01570.0416*
H20.27900.47370.24480.0668*
H30.17920.48890.11970.0870*
H40.17220.46670.10640.0899*
H50.26510.42950.20760.0825*
H60.36490.41420.08260.0626*
H70.31800.36320.21070.0501*
H80.34180.28620.22110.0597*
H90.45410.26020.18200.0710*
H100.54250.31110.13230.0712*
H110.51870.38810.12190.0581*
H120.49670.43880.66700.0474*
H130.44270.42860.55550.0474*
H140.51840.39420.42970.0514*
H150.58020.41480.50760.0514*
H160.56020.36930.68830.0520*
H170.48930.33750.84520.0636*
H180.37940.31310.90990.0798*
H190.29280.30400.74740.0795*
H200.31620.31930.52040.0730*
H210.42620.34370.45580.0593*
H220.51330.28380.46590.0860*
H230.58970.23310.36500.1183*
H240.70890.24480.38040.1161*
H250.75160.30720.49680.1047*
H260.67520.35790.59770.0825*
H270.24060.40920.44490.0864*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0421 (3)0.0223 (2)0.0279 (3)0.0042 (3)0.0015 (3)0.0007 (3)
Cl10.0811 (10)0.0693 (9)0.193 (2)0.0002 (8)0.023 (1)0.021 (1)
Cl20.115 (1)0.189 (2)0.096 (1)0.005 (1)0.004 (1)0.025 (1)
Cl30.0743 (9)0.110 (1)0.121 (1)0.0162 (9)0.0226 (9)0.050 (1)
O10.055 (2)0.044 (1)0.032 (1)0.021 (1)0.004 (1)0.002 (1)
O20.042 (1)0.040 (1)0.037 (1)0.006 (1)0.007 (1)0.001 (1)
N10.040 (2)0.027 (1)0.029 (1)0.007 (1)0.002 (1)0.002 (1)
N20.043 (2)0.032 (1)0.028 (1)0.009 (1)0.004 (1)0.002 (1)
N30.057 (2)0.027 (1)0.033 (2)0.006 (1)0.002 (1)0.002 (1)
C10.038 (2)0.029 (2)0.032 (2)0.003 (1)0.001 (1)0.000 (1)
C20.037 (2)0.025 (2)0.038 (2)0.001 (1)0.000 (2)0.002 (1)
C30.035 (2)0.025 (2)0.034 (2)0.003 (1)0.002 (1)0.001 (1)
C40.043 (2)0.029 (2)0.040 (2)0.003 (1)0.005 (2)0.003 (1)
C50.049 (2)0.051 (2)0.066 (3)0.007 (2)0.007 (2)0.006 (2)
C60.045 (3)0.071 (3)0.106 (4)0.013 (2)0.005 (3)0.021 (3)
C70.062 (3)0.067 (3)0.097 (4)0.020 (3)0.036 (3)0.037 (3)
C80.081 (3)0.058 (3)0.062 (3)0.015 (2)0.032 (3)0.012 (2)
C90.059 (3)0.047 (2)0.048 (2)0.004 (2)0.017 (2)0.002 (2)
C100.043 (2)0.029 (2)0.031 (2)0.000 (1)0.004 (2)0.003 (1)
C110.046 (2)0.034 (2)0.045 (2)0.006 (2)0.001 (2)0.002 (2)
C120.061 (3)0.033 (2)0.056 (2)0.008 (2)0.003 (2)0.002 (2)
C130.078 (3)0.031 (2)0.068 (3)0.009 (2)0.011 (2)0.003 (2)
C140.056 (2)0.048 (2)0.074 (3)0.018 (2)0.003 (2)0.005 (2)
C150.046 (2)0.039 (2)0.059 (3)0.002 (2)0.003 (2)0.004 (2)
C160.050 (2)0.031 (2)0.047 (2)0.004 (2)0.003 (2)0.006 (2)
C170.050 (2)0.035 (2)0.045 (2)0.004 (2)0.010 (2)0.004 (2)
C180.046 (2)0.025 (2)0.045 (2)0.002 (2)0.004 (2)0.001 (1)
C190.067 (3)0.045 (2)0.046 (2)0.002 (2)0.001 (2)0.003 (2)
C200.086 (3)0.061 (3)0.052 (3)0.002 (3)0.024 (3)0.004 (2)
C210.055 (3)0.053 (3)0.089 (4)0.004 (2)0.016 (3)0.001 (3)
C220.049 (2)0.055 (2)0.080 (3)0.005 (2)0.011 (2)0.001 (2)
C230.056 (2)0.043 (2)0.049 (2)0.010 (2)0.007 (2)0.007 (2)
C240.046 (2)0.039 (2)0.057 (2)0.004 (2)0.000 (2)0.010 (2)
C250.055 (3)0.046 (2)0.115 (5)0.001 (2)0.013 (3)0.016 (3)
C260.080 (4)0.065 (3)0.147 (6)0.008 (3)0.017 (4)0.033 (4)
C270.084 (4)0.086 (4)0.121 (5)0.036 (3)0.024 (4)0.005 (4)
C280.055 (3)0.117 (5)0.090 (4)0.017 (3)0.004 (3)0.002 (4)
C290.055 (3)0.077 (3)0.078 (3)0.002 (2)0.004 (2)0.001 (3)
C300.042 (2)0.081 (3)0.092 (4)0.008 (2)0.008 (2)0.016 (3)
Geometric parameters (Å, º) top
Cu1—N12.009 (3)C13—C141.390 (3)
Cu1—N32.005 (3)C13—H90.950
Cl1—C301.742 (5)C14—C151.390 (3)
Cl2—C301.761 (6)C14—H100.950
Cl3—C301.725 (6)C15—H110.950
O1—C11.232 (4)C16—C171.547 (5)
O2—C21.222 (4)C16—H140.950
N1—C11.401 (4)C16—H150.950
N1—C21.372 (4)C17—C181.512 (4)
N2—C11.346 (4)C17—C241.534 (4)
N2—C31.460 (4)C17—H160.950
N2—H10.950C18—C191.390 (3)
N3—C161.482 (4)C18—C231.390 (3)
N3—H120.950C19—C201.390 (4)
N3—H130.950C19—H170.950
C2—C31.549 (5)C20—C211.390 (4)
C3—C41.532 (4)C20—H180.950
C3—C101.529 (3)C21—C221.390 (4)
C4—C51.390 (4)C21—H190.950
C4—C91.390 (3)C22—C231.390 (3)
C5—C61.390 (4)C22—H200.950
C5—H20.950C23—H210.950
C6—C71.390 (5)C24—C251.390 (4)
C6—H30.950C24—C291.390 (4)
C7—C81.390 (4)C25—C261.390 (4)
C7—H40.950C25—H220.950
C8—C91.390 (4)C26—C271.390 (5)
C8—H50.950C26—H230.950
C9—H60.950C27—C281.390 (5)
C10—C111.390 (3)C27—H240.950
C10—C151.390 (3)C28—C291.390 (4)
C11—C121.390 (3)C28—H250.950
C11—H70.950C29—H260.950
C12—C131.390 (4)C30—H270.950
C12—H80.950
N1—Cu1—N1i180.0C13—C14—H10120.0
N1—Cu1—N389.2 (1)C15—C14—H10120.0
N1—Cu1—N3i90.8 (1)C10—C15—C14120.0 (2)
N3—Cu1—N3i180.0C10—C15—H11119.9
Cu1—N1—C1123.8 (2)C14—C15—H11120.1
Cu1—N1—C2127.3 (2)N3—C16—C17112.6 (3)
C1—N1—C2107.6 (3)N3—C16—H14108.7
C1—N2—C3111.4 (3)N3—C16—H15108.5
C1—N2—H1124.3C17—C16—H14108.8
C3—N2—H1124.3C17—C16—H15108.7
Cu1—N3—C16117.0 (2)H14—C16—H15109.3
Cu1—N3—H12107.6C16—C17—C18112.3 (3)
Cu1—N3—H13107.3C16—C17—C24109.5 (3)
C16—N3—H12107.8C16—C17—H16106.4
C16—N3—H13107.5C18—C17—C24115.2 (3)
H12—N3—H13109.5C18—C17—H16106.3
O1—C1—N1123.8 (3)C24—C17—H16106.5
O1—C1—N2125.2 (3)C17—C18—C19118.7 (2)
N1—C1—N2111.1 (3)C17—C18—C23121.2 (2)
O2—C2—N1126.3 (3)C19—C18—C23120.0 (2)
O2—C2—C3124.2 (3)C18—C19—C20120.0 (2)
N1—C2—C3109.4 (3)C18—C19—H17120.0
N2—C3—C2100.0 (2)C20—C19—H17120.0
N2—C3—C4109.8 (2)C19—C20—C21120.0 (2)
N2—C3—C10113.4 (2)C19—C20—H18120.1
C2—C3—C4114.9 (2)C21—C20—H18119.9
C2—C3—C10107.3 (2)C20—C21—C22120.0 (2)
C4—C3—C10111.1 (2)C20—C21—H19120.1
C3—C4—C5123.3 (2)C22—C21—H19119.9
C3—C4—C9116.6 (2)C21—C22—C23120.0 (2)
C5—C4—C9120.0 (2)C21—C22—H20120.1
C4—C5—C6120.0 (2)C23—C22—H20119.9
C4—C5—H2120.1C18—C23—C22120.0 (2)
C6—C5—H2119.9C18—C23—H21119.9
C5—C6—C7120.0 (2)C22—C23—H21120.1
C5—C6—H3119.9C17—C24—C25121.8 (2)
C7—C6—H3120.1C17—C24—C29118.2 (3)
C6—C7—C8120.0 (2)C25—C24—C29120.0 (2)
C6—C7—H4119.8C24—C25—C26120.0 (2)
C8—C7—H4120.2C24—C25—H22119.9
C7—C8—C9120.0 (2)C26—C25—H22120.1
C7—C8—H5119.9C25—C26—C27120.0 (3)
C9—C8—H5120.1C25—C26—H23119.9
C4—C9—C8120.0 (2)C27—C26—H23120.1
C4—C9—H6119.9C26—C27—C28120.0 (3)
C8—C9—H6120.1C26—C27—H24119.9
C3—C10—C11118.7 (2)C28—C27—H24120.1
C3—C10—C15121.3 (2)C27—C28—C29120.0 (2)
C11—C10—C15120.0 (2)C27—C28—H25119.9
C10—C11—C12120.0 (2)C29—C28—H25120.1
C10—C11—H7120.0C24—C29—C28120.0 (3)
C12—C11—H7120.0C24—C29—H26120.1
C11—C12—C13120.0 (2)C28—C29—H26119.9
C11—C12—H8120.0Cl1—C30—Cl2110.9 (3)
C13—C12—H8120.0Cl1—C30—Cl3110.3 (3)
C12—C13—C14120.0 (2)Cl1—C30—H27108.8
C12—C13—H9120.0Cl2—C30—Cl3109.3 (3)
C14—C13—H9120.0Cl2—C30—H27108.6
C13—C14—C15120.0 (2)Cl3—C30—H27108.9
Cu1—N1—C1—O118.9 (5)C4—C3—C10—C1144.1 (3)
Cu1—N1—C1—N2160.4 (2)C4—C3—C10—C15138.6 (3)
Cu1—N1—C2—O215.3 (5)C4—C5—C6—C70.0 (4)
Cu1—N1—C2—C3161.7 (2)C4—C9—C8—C70.0 (4)
Cu1—N1i—C1i—O1i18.9 (5)C5—C4—C3—C10123.3 (3)
Cu1—N1i—C1i—N2i160.4 (2)C5—C4—C9—C80.0 (4)
Cu1—N1i—C2i—O2i15.3 (5)C5—C6—C7—C80.0 (5)
Cu1—N1i—C2i—C3i161.7 (2)C6—C5—C4—C90.0 (4)
Cu1—N3—C16—C17162.3 (2)C6—C7—C8—C90.0 (5)
Cu1—N3i—C16i—C17i162.3 (2)C9—C4—C3—C1059.4 (3)
O1—C1—N1—C2173.1 (3)C10—C11—C12—C130.0 (4)
O1—C1—N2—C3174.3 (3)C10—C15—C14—C130.0 (4)
O2—C2—N1—C1177.3 (3)C11—C10—C15—C140.0 (4)
O2—C2—C3—N2179.1 (3)C11—C12—C13—C140.0 (4)
O2—C2—C3—C1060.5 (4)C12—C11—C10—C150.0 (4)
N1—Cu1—N3i—C16i106.8 (2)C12—C13—C14—C150.0 (4)
N1—C1—N2—C36.4 (4)C16—C17—C18—C19130.1 (3)
N1—C2—C3—N22.0 (3)C16—C17—C18—C2347.7 (4)
N1—C2—C3—C4119.4 (3)C16—C17—C24—C25102.2 (4)
N1—C2—C3—C10116.6 (3)C16—C17—C24—C2976.6 (4)
N2—C1—N1—C27.6 (4)C17—C18—C19—C20177.8 (3)
N2—C3—C4—C5110.4 (3)C17—C18—C23—C22177.7 (3)
N2—C3—C4—C966.9 (3)C17—C24—C25—C26178.8 (3)
N2—C3—C10—C11168.3 (2)C17—C24—C29—C28178.8 (3)
N2—C3—C10—C1514.4 (4)C18—C17—C24—C2525.5 (4)
N3—Cu1—N1—C1130.9 (3)C18—C17—C24—C29155.7 (3)
N3—Cu1—N1—C234.6 (3)C18—C19—C20—C210.0 (4)
N3—Cu1—N1i—C1i49.1 (3)C18—C23—C22—C210.0 (4)
N3—Cu1—N1i—C2i145.4 (3)C19—C18—C17—C24103.7 (3)
N3—C16—C17—C24179.8 (3)C19—C18—C23—C220.0 (4)
C1—N1—C2—C35.7 (3)C19—C20—C21—C220.0 (4)
C1—N2—C3—C22.7 (3)C20—C19—C18—C230.0 (4)
C1—N2—C3—C4118.5 (3)C20—C21—C22—C230.0 (4)
C1—N2—C3—C10116.6 (3)C23—C18—C17—C2478.6 (4)
C2—C3—C4—C51.3 (4)C24—C25—C26—C270.0 (5)
C2—C3—C4—C9178.6 (2)C24—C29—C28—C270.0 (5)
C2—C3—C10—C1182.2 (3)C25—C24—C29—C280.0 (5)
C2—C3—C10—C1595.1 (3)C25—C26—C27—C280.0 (6)
C3—C4—C5—C6177.2 (3)C26—C25—C24—C290.0 (5)
C3—C4—C9—C8177.4 (2)C26—C27—C28—C290.0 (6)
C3—C10—C11—C12177.3 (2)C26—C27—C28—C290.0 (6)
C3—C10—C15—C14177.2 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O1ii0.952.022.900 (3)153
N3—H12···O1i0.952.062.837 (3)137
N3—H13···O20.952.132.922 (3)140
C30—H27···O20.952.573.507 (5)170
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z.
(II) top
Crystal data top
[Cu(C15H11N2O2)2(C14H15N)2]Z = 2
Mr = 960.63F(000) = 1006
Triclinic, P1Dx = 1.327 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 14.313 (4) ÅCell parameters from 25 reflections
b = 15.888 (5) Åθ = 10.0–12.4°
c = 11.863 (4) ŵ = 0.51 mm1
α = 90.13 (3)°T = 298 K
β = 95.00 (3)°Plate-like, blue–violet
γ = 63.58 (2)°0.50 × 0.40 × 0.20 mm
V = 2404.7 (14) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.087
ω/2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 1818
Tmin = 0.783, Tmax = 0.903k = 2020
12233 measured reflectionsl = 615
12233 independent reflections3 standard reflections every 150 reflections
11075 reflections with I > 0σ(I) intensity decay: 0.3%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.069 w = 1/[σ2(Fo2) + (0.0502P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.161(Δ/σ)max < 0.001
S = 0.85Δρmax = 0.62 e Å3
11075 reflectionsΔρmin = 1.31 e Å3
527 parameters
Crystal data top
[Cu(C15H11N2O2)2(C14H15N)2]γ = 63.58 (2)°
Mr = 960.63V = 2404.7 (14) Å3
Triclinic, P1Z = 2
a = 14.313 (4) ÅMo Kα radiation
b = 15.888 (5) ŵ = 0.51 mm1
c = 11.863 (4) ÅT = 298 K
α = 90.13 (3)°0.50 × 0.40 × 0.20 mm
β = 95.00 (3)°
Data collection top
Rigaku AFC-7R
diffractometer
11075 reflections with I > 0σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.087
Tmin = 0.783, Tmax = 0.9033 standard reflections every 150 reflections
12233 measured reflections intensity decay: 0.3%
12233 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069527 parameters
wR(F2) = 0.161H-atom parameters constrained
S = 0.85Δρmax = 0.62 e Å3
11075 reflectionsΔρmin = 1.31 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.99199 (5)0.48877 (4)0.29269 (5)0.0246 (2)
O11.0577 (2)0.4010 (2)0.0607 (3)0.0412 (9)
O20.7685 (3)0.4529 (2)0.2396 (3)0.0397 (9)
O31.1150 (2)0.4528 (2)0.5536 (3)0.0298 (8)
O41.1108 (2)0.6262 (2)0.2463 (3)0.0349 (8)
N10.9244 (3)0.4360 (3)0.1786 (3)0.0279 (9)
N20.9004 (3)0.4027 (3)0.0037 (3)0.0324 (10)
N30.9143 (3)0.6129 (3)0.2026 (3)0.0278 (9)
N41.0937 (3)0.5284 (3)0.3785 (3)0.0235 (9)
N51.2063 (3)0.5348 (3)0.5203 (3)0.0314 (10)
N61.0715 (3)0.3589 (3)0.3699 (3)0.0317 (10)
C10.9685 (4)0.4116 (3)0.0750 (4)0.030 (1)
C20.8292 (4)0.4377 (3)0.1662 (4)0.031 (1)
C30.8029 (3)0.4189 (3)0.0426 (4)0.025 (1)
C40.7880 (3)0.3298 (2)0.0300 (3)0.034 (1)
C50.8239 (3)0.2610 (3)0.1168 (2)0.072 (2)
C60.8201 (4)0.1761 (2)0.0992 (3)0.092 (3)
C70.7802 (4)0.1599 (2)0.0053 (4)0.063 (2)
C80.7443 (3)0.2287 (3)0.0921 (3)0.059 (2)
C90.7481 (3)0.3137 (2)0.0744 (3)0.049 (1)
C100.7094 (2)0.5085 (2)0.0082 (3)0.030 (1)
C110.6111 (3)0.5302 (2)0.0261 (3)0.043 (1)
C120.5255 (2)0.6140 (3)0.0119 (4)0.057 (2)
C130.5381 (3)0.6760 (2)0.0843 (4)0.068 (2)
C140.6364 (3)0.6544 (2)0.1186 (3)0.057 (2)
C150.7221 (2)0.5706 (3)0.0806 (3)0.044 (1)
C160.8022 (4)0.6693 (3)0.2186 (4)0.033 (1)
C170.7472 (4)0.7552 (3)0.1361 (4)0.033 (1)
C180.6293 (2)0.8074 (3)0.1473 (3)0.039 (1)
C190.5650 (3)0.8633 (3)0.0552 (3)0.058 (2)
C200.4577 (3)0.9138 (3)0.0619 (3)0.073 (2)
C210.4148 (2)0.9085 (3)0.1607 (4)0.068 (2)
C220.4791 (3)0.8526 (3)0.2528 (3)0.081 (2)
C230.5864 (3)0.8020 (3)0.2462 (3)0.077 (2)
C240.8010 (3)0.8194 (2)0.1466 (3)0.038 (1)
C250.7791 (3)0.8839 (3)0.2317 (3)0.058 (2)
C260.8346 (4)0.9366 (3)0.2466 (4)0.074 (2)
C270.9119 (3)0.9250 (3)0.1763 (4)0.082 (2)
C280.9338 (3)0.8605 (3)0.0912 (4)0.077 (2)
C290.8784 (3)0.8077 (3)0.0763 (3)0.057 (2)
C301.1366 (3)0.5020 (3)0.4901 (4)0.025 (1)
C311.1328 (3)0.5871 (3)0.3411 (4)0.027 (1)
C321.2061 (3)0.6000 (3)0.4340 (4)0.027 (1)
C331.1617 (3)0.6985 (2)0.4796 (3)0.032 (1)
C341.0631 (3)0.7685 (3)0.4410 (3)0.061 (2)
C351.0255 (3)0.8566 (2)0.4874 (4)0.086 (2)
C361.0864 (4)0.8748 (2)0.5724 (4)0.068 (2)
C371.1851 (4)0.8048 (3)0.6111 (3)0.072 (2)
C381.2227 (2)0.7166 (3)0.5647 (3)0.056 (2)
C391.3152 (2)0.5693 (3)0.3915 (3)0.034 (1)
C401.3475 (3)0.6353 (2)0.3584 (3)0.052 (2)
C411.4448 (3)0.6058 (3)0.3175 (4)0.072 (2)
C421.5098 (2)0.5104 (3)0.3096 (3)0.066 (2)
C431.4775 (3)0.4444 (2)0.3426 (4)0.075 (2)
C441.3801 (3)0.4739 (2)0.3836 (4)0.058 (2)
C451.1778 (4)0.3075 (3)0.3330 (4)0.040 (1)
C461.2445 (4)0.2093 (4)0.3910 (4)0.039 (1)
C471.3600 (2)0.1808 (3)0.3729 (3)0.043 (1)
C481.4149 (3)0.2214 (3)0.4356 (3)0.061 (2)
C491.5179 (3)0.1979 (3)0.4167 (4)0.078 (2)
C501.5660 (2)0.1339 (3)0.3352 (4)0.076 (2)
C511.5111 (3)0.0934 (3)0.2725 (3)0.072 (2)
C521.4081 (3)0.1168 (3)0.2914 (3)0.054 (2)
C531.2101 (3)0.1341 (2)0.3606 (3)0.041 (1)
C541.2504 (3)0.0531 (3)0.4303 (3)0.054 (2)
C551.2255 (3)0.0200 (2)0.4026 (4)0.066 (2)
C561.1603 (3)0.0122 (3)0.3051 (4)0.072 (2)
C571.1200 (3)0.0688 (3)0.2354 (3)0.074 (2)
C581.1449 (3)0.1419 (2)0.2632 (3)0.060 (2)
H10.91410.38770.08000.0386*
H20.85100.27200.18820.0871*
H30.84450.12910.15840.1109*
H40.77750.10190.01750.0752*
H50.71710.21770.16360.0711*
H60.72370.36070.13380.0593*
H70.60250.48780.07560.0515*
H80.45830.62870.01160.0685*
H90.47950.73320.11030.0812*
H100.64500.69670.16810.0681*
H110.78930.55580.10400.0522*
H120.94910.65050.22250.0331*
H130.91890.59970.12460.0331*
H140.76780.63030.20790.0397*
H150.79700.69050.29390.0397*
H160.75490.73210.06190.0388*
H170.59440.86700.01230.0701*
H180.41380.95200.00110.0879*
H190.34140.94300.16520.0807*
H200.44970.84890.32030.0979*
H210.63030.76390.30920.0925*
H220.72630.89180.27970.0701*
H230.81960.98070.30470.0880*
H240.94980.96110.18640.0983*
H250.98660.85260.04310.0923*
H260.89330.76370.01810.0684*
H271.25020.51780.58940.0375*
H281.02150.75610.38270.0732*
H290.95800.90450.46080.1035*
H301.06060.93510.60410.0813*
H311.22650.81730.66930.0859*
H321.29000.66890.59110.0676*
H331.30310.70050.36380.0630*
H341.46700.65090.29490.0869*
H351.57630.49030.28160.0787*
H361.52180.37920.33720.0898*
H371.35800.42880.40620.0698*
H381.07720.36560.44960.0380*
H391.03360.32370.35230.0380*
H401.17120.30000.25370.0480*
H411.21420.34460.34840.0480*
H421.23910.21740.46990.0468*
H431.38200.26500.49150.0733*
H441.55550.22560.45970.0940*
H451.63650.11790.32250.0920*
H461.54410.04970.21690.0871*
H471.37060.08910.24860.0647*
H481.29480.04790.49700.0651*
H491.25290.07530.45030.0795*
H501.14320.06220.28620.0863*
H511.07550.07410.16880.0883*
H521.11740.19720.21550.0720*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0241 (3)0.0258 (3)0.0235 (3)0.0109 (3)0.0019 (3)0.0015 (3)
O10.026 (2)0.060 (2)0.043 (2)0.024 (2)0.006 (2)0.004 (2)
O20.045 (2)0.063 (2)0.022 (2)0.031 (2)0.015 (2)0.009 (2)
O30.035 (2)0.033 (2)0.024 (2)0.016 (2)0.003 (1)0.004 (1)
O40.040 (2)0.048 (2)0.021 (2)0.024 (2)0.000 (2)0.008 (2)
N10.030 (2)0.036 (2)0.016 (2)0.014 (2)0.000 (2)0.000 (2)
N20.033 (2)0.049 (3)0.018 (2)0.021 (2)0.006 (2)0.006 (2)
N30.026 (2)0.029 (2)0.026 (2)0.012 (2)0.003 (2)0.005 (2)
N40.022 (2)0.031 (2)0.019 (2)0.013 (2)0.001 (2)0.005 (2)
N50.028 (2)0.039 (2)0.027 (2)0.015 (2)0.003 (2)0.004 (2)
N60.030 (2)0.031 (2)0.030 (2)0.011 (2)0.003 (2)0.001 (2)
C10.037 (3)0.034 (3)0.026 (3)0.022 (2)0.001 (2)0.000 (2)
C20.037 (3)0.036 (3)0.020 (3)0.017 (2)0.002 (2)0.004 (2)
C30.028 (3)0.040 (3)0.015 (2)0.021 (2)0.006 (2)0.005 (2)
C40.039 (3)0.033 (3)0.034 (3)0.020 (2)0.006 (2)0.003 (2)
C50.123 (6)0.053 (4)0.051 (4)0.053 (4)0.009 (4)0.004 (3)
C60.181 (8)0.066 (5)0.046 (4)0.073 (5)0.007 (5)0.001 (4)
C70.086 (5)0.045 (4)0.065 (4)0.034 (4)0.003 (4)0.022 (3)
C80.073 (4)0.055 (4)0.052 (4)0.034 (4)0.007 (3)0.007 (3)
C90.079 (4)0.054 (4)0.032 (3)0.045 (3)0.009 (3)0.009 (3)
C100.032 (3)0.035 (3)0.028 (3)0.019 (2)0.004 (2)0.006 (2)
C110.037 (3)0.044 (3)0.051 (4)0.019 (3)0.011 (3)0.003 (3)
C120.041 (4)0.059 (4)0.070 (4)0.020 (3)0.009 (3)0.001 (3)
C130.047 (4)0.057 (4)0.087 (5)0.015 (3)0.011 (4)0.009 (4)
C140.065 (4)0.058 (4)0.048 (4)0.030 (4)0.007 (3)0.021 (3)
C150.045 (3)0.055 (4)0.044 (3)0.031 (3)0.010 (3)0.002 (3)
C160.032 (3)0.031 (3)0.033 (3)0.010 (2)0.006 (2)0.004 (2)
C170.035 (3)0.027 (3)0.028 (3)0.007 (2)0.004 (2)0.001 (2)
C180.037 (3)0.023 (3)0.047 (3)0.005 (2)0.003 (3)0.001 (2)
C190.041 (3)0.066 (4)0.044 (4)0.003 (3)0.002 (3)0.005 (3)
C200.042 (4)0.076 (5)0.072 (5)0.002 (4)0.010 (3)0.007 (4)
C210.032 (3)0.046 (4)0.116 (6)0.009 (3)0.010 (4)0.027 (4)
C220.045 (4)0.094 (6)0.084 (5)0.009 (4)0.025 (4)0.017 (4)
C230.040 (4)0.090 (5)0.073 (5)0.003 (4)0.013 (3)0.026 (4)
C240.030 (3)0.033 (3)0.037 (3)0.002 (2)0.003 (2)0.010 (2)
C250.054 (4)0.045 (4)0.073 (5)0.019 (3)0.009 (3)0.015 (3)
C260.054 (4)0.054 (4)0.111 (6)0.022 (4)0.012 (4)0.034 (4)
C270.063 (5)0.045 (4)0.141 (8)0.029 (4)0.002 (5)0.015 (5)
C280.066 (5)0.065 (5)0.108 (6)0.034 (4)0.020 (4)0.021 (4)
C290.064 (4)0.056 (4)0.058 (4)0.029 (3)0.021 (3)0.004 (3)
C300.021 (2)0.026 (3)0.026 (3)0.008 (2)0.005 (2)0.001 (2)
C310.024 (3)0.034 (3)0.021 (3)0.011 (2)0.005 (2)0.011 (2)
C320.030 (3)0.036 (3)0.019 (2)0.019 (2)0.002 (2)0.001 (2)
C330.040 (3)0.047 (3)0.023 (3)0.030 (3)0.011 (2)0.004 (2)
C340.045 (4)0.048 (4)0.074 (5)0.009 (3)0.002 (3)0.016 (3)
C350.056 (4)0.060 (5)0.125 (7)0.013 (4)0.001 (4)0.018 (5)
C360.089 (5)0.058 (4)0.073 (5)0.043 (4)0.033 (4)0.023 (4)
C370.113 (6)0.068 (5)0.057 (4)0.057 (5)0.024 (4)0.029 (4)
C380.065 (4)0.059 (4)0.046 (4)0.030 (3)0.003 (3)0.007 (3)
C390.024 (3)0.054 (3)0.026 (3)0.019 (3)0.000 (2)0.000 (2)
C400.038 (3)0.067 (4)0.057 (4)0.026 (3)0.010 (3)0.010 (3)
C410.048 (4)0.112 (6)0.069 (5)0.044 (4)0.013 (3)0.020 (4)
C420.035 (4)0.118 (6)0.045 (4)0.034 (4)0.007 (3)0.002 (4)
C430.043 (4)0.081 (5)0.090 (5)0.016 (4)0.024 (4)0.016 (4)
C440.045 (4)0.057 (4)0.075 (5)0.022 (3)0.021 (3)0.016 (3)
C450.036 (3)0.026 (3)0.043 (3)0.001 (2)0.002 (2)0.002 (2)
C460.038 (3)0.037 (3)0.032 (3)0.007 (3)0.006 (2)0.002 (2)
C470.044 (3)0.027 (3)0.047 (3)0.005 (3)0.006 (3)0.010 (3)
C480.058 (4)0.065 (4)0.051 (4)0.021 (4)0.006 (3)0.005 (3)
C490.055 (5)0.092 (6)0.086 (6)0.034 (4)0.012 (4)0.012 (5)
C500.038 (4)0.075 (5)0.097 (6)0.008 (4)0.005 (4)0.020 (4)
C510.055 (4)0.056 (4)0.092 (6)0.007 (4)0.033 (4)0.005 (4)
C520.051 (4)0.046 (4)0.062 (4)0.018 (3)0.012 (3)0.003 (3)
C530.031 (3)0.037 (3)0.047 (3)0.007 (3)0.006 (3)0.003 (3)
C540.048 (4)0.035 (3)0.069 (4)0.010 (3)0.004 (3)0.013 (3)
C550.057 (4)0.050 (4)0.093 (5)0.023 (3)0.018 (4)0.007 (4)
C560.053 (4)0.049 (4)0.120 (7)0.023 (4)0.030 (4)0.021 (4)
C570.062 (4)0.062 (5)0.092 (6)0.024 (4)0.001 (4)0.022 (4)
C580.059 (4)0.045 (4)0.067 (4)0.018 (3)0.003 (3)0.006 (3)
Geometric parameters (Å, º) top
Cu1—O3i2.397 (4)C23—H210.950
Cu1—N11.990 (4)C24—C251.390 (5)
Cu1—N32.030 (3)C24—C291.390 (6)
Cu1—N42.026 (4)C25—C261.390 (7)
Cu1—N62.032 (4)C25—H220.950
O1—C11.238 (7)C26—C271.390 (7)
O2—C21.232 (6)C26—H230.950
O3—C301.237 (7)C27—C281.390 (7)
O4—C311.232 (6)C27—H240.950
N1—C11.405 (6)C28—C291.390 (8)
N1—C21.345 (7)C28—H250.950
N2—C11.343 (7)C29—H260.950
N2—C31.459 (7)C31—C321.532 (7)
N2—H10.950C32—C331.522 (6)
N3—C161.478 (6)C32—C391.545 (6)
N3—H120.950C33—C341.390 (4)
N3—H130.950C33—C381.390 (5)
N4—C301.392 (5)C34—C351.390 (6)
N4—C311.374 (7)C34—H280.950
N5—C301.340 (7)C35—C361.390 (7)
N5—C321.457 (7)C35—H290.950
N5—H270.950C36—C371.390 (5)
N6—C451.478 (6)C36—H300.950
N6—H380.950C37—C381.390 (6)
N6—H390.950C37—H310.950
C2—C31.544 (6)C38—H320.950
C3—C41.528 (7)C39—C401.390 (6)
C3—C101.532 (4)C39—C441.390 (4)
C4—C51.390 (5)C40—C411.390 (6)
C4—C91.390 (5)C40—H330.950
C5—C61.390 (7)C41—C421.390 (6)
C5—H20.950C41—H340.950
C6—C71.390 (6)C42—C431.390 (7)
C6—H30.950C42—H350.950
C7—C81.390 (5)C43—C441.390 (6)
C7—H40.950C43—H360.950
C8—C91.390 (6)C44—H370.950
C8—H50.950C45—C461.544 (6)
C9—H60.950C45—H400.950
C10—C111.390 (5)C45—H410.950
C10—C151.390 (6)C46—C471.541 (6)
C11—C121.390 (4)C46—C531.515 (8)
C11—H70.950C46—H420.950
C12—C131.390 (6)C47—C481.390 (7)
C12—H80.950C47—C521.390 (5)
C13—C141.390 (6)C48—C491.390 (7)
C13—H90.950C48—H430.950
C14—C151.390 (4)C49—C501.390 (7)
C14—H100.950C49—H440.950
C15—H110.950C50—C511.390 (7)
C16—C171.536 (6)C50—H450.950
C16—H140.950C51—C521.390 (7)
C16—H150.950C51—H460.950
C17—C181.532 (5)C52—H470.950
C17—C241.526 (8)C53—C541.390 (5)
C17—H160.950C53—C581.390 (5)
C18—C191.390 (4)C54—C551.390 (7)
C18—C231.390 (6)C54—H480.950
C19—C201.390 (5)C55—C561.390 (7)
C19—H170.950C55—H490.950
C20—C211.390 (6)C56—C571.390 (6)
C20—H180.950C56—H500.950
C21—C221.390 (6)C57—C581.390 (7)
C21—H190.950C57—H510.950
C22—C231.390 (6)C58—H520.950
C22—H200.950
O3i—Cu1—N1109.8 (1)C17—C24—C29119.5 (3)
O3i—Cu1—N392.2 (1)C25—C24—C29120.0 (4)
O3i—Cu1—N486.7 (1)C24—C25—C26120.0 (4)
O3i—Cu1—N691.9 (1)C24—C25—H22120.0
N1—Cu1—N386.9 (2)C26—C25—H22120.0
N1—Cu1—N4163.5 (2)C25—C26—C27120.0 (4)
N1—Cu1—N689.1 (2)C25—C26—H23120.0
N3—Cu1—N493.7 (2)C27—C26—H23120.0
N3—Cu1—N6175.0 (2)C26—C27—C28120.0 (5)
N4—Cu1—N689.2 (2)C26—C27—H24120.0
Cu1—N1—C1117.1 (4)C28—C27—H24120.0
Cu1—N1—C2132.8 (3)C27—C28—C29120.0 (4)
C1—N1—C2108.0 (4)C27—C28—H25120.0
C1—N2—C3111.6 (4)C29—C28—H25120.0
C1—N2—H1124.2C24—C29—C28120.0 (4)
C3—N2—H1124.2C24—C29—H26120.0
Cu1—N3—C16117.1 (3)C28—C29—H26120.0
Cu1—N3—H12107.5O3—C30—N4124.7 (5)
Cu1—N3—H13107.6O3—C30—N5123.7 (4)
C16—N3—H12107.5N4—C30—N5111.7 (5)
C16—N3—H13107.5O4—C31—N4125.0 (5)
H12—N3—H13109.5O4—C31—C32123.8 (5)
Cu1—N4—C30125.9 (4)N4—C31—C32111.2 (4)
Cu1—N4—C31128.0 (3)N5—C32—C3198.9 (4)
C30—N4—C31106.1 (4)N5—C32—C33108.9 (3)
C30—N5—C32111.6 (4)N5—C32—C39112.7 (3)
C30—N5—H27124.2C31—C32—C33113.5 (3)
C32—N5—H27124.2C31—C32—C39109.7 (3)
Cu1—N6—C45112.0 (3)C33—C32—C39112.5 (4)
Cu1—N6—H38108.8C32—C33—C34122.4 (4)
Cu1—N6—H39108.9C32—C33—C38117.6 (3)
C45—N6—H38108.8C34—C33—C38120.0 (3)
C45—N6—H39108.9C33—C34—C35120.0 (4)
H38—N6—H39109.5C33—C34—H28120.0
O1—C1—N1123.4 (5)C35—C34—H28120.0
O1—C1—N2126.1 (4)C34—C35—C36120.0 (3)
N1—C1—N2110.5 (5)C34—C35—H29120.0
O2—C2—N1127.0 (4)C36—C35—H29120.0
O2—C2—C3122.7 (5)C35—C36—C37120.0 (3)
N1—C2—C3110.3 (4)C35—C36—H30119.9
N2—C3—C299.5 (4)C37—C36—H30120.1
N2—C3—C4108.3 (3)C36—C37—C38120.0 (4)
N2—C3—C10112.5 (4)C36—C37—H31119.9
C2—C3—C4113.7 (4)C38—C37—H31120.1
C2—C3—C10107.6 (3)C33—C38—C37120.0 (3)
C4—C3—C10114.3 (4)C33—C38—H32120.0
C3—C4—C5121.0 (4)C37—C38—H32120.0
C3—C4—C9118.6 (3)C32—C39—C40121.2 (3)
C5—C4—C9120.0 (4)C32—C39—C44118.8 (4)
C4—C5—C6120.0 (3)C40—C39—C44120.0 (3)
C4—C5—H2120.0C39—C40—C41120.0 (3)
C6—C5—H2120.0C39—C40—H33120.0
C5—C6—C7120.0 (3)C41—C40—H33120.0
C5—C6—H3120.1C40—C41—C42120.0 (5)
C7—C6—H3119.9C40—C41—H34120.0
C6—C7—C8120.0 (4)C42—C41—H34120.0
C6—C7—H4120.1C41—C42—C43120.0 (4)
C8—C7—H4119.9C41—C42—H35120.0
C7—C8—C9120.0 (3)C43—C42—H35120.0
C7—C8—H5120.1C42—C43—C44120.0 (3)
C9—C8—H5119.9C42—C43—H36120.0
C4—C9—C8120.0 (3)C44—C43—H36120.0
C4—C9—H6120.0C39—C44—C43120.0 (4)
C8—C9—H6120.0C39—C44—H37120.0
C3—C10—C11118.1 (3)C43—C44—H37120.0
C3—C10—C15121.7 (3)N6—C45—C46115.0 (5)
C11—C10—C15120.0 (2)N6—C45—H40108.1
C10—C11—C12120.0 (4)N6—C45—H41108.1
C10—C11—H7120.0C46—C45—H40108.1
C12—C11—H7120.0C46—C45—H41108.0
C11—C12—C13120.0 (3)H40—C45—H41109.3
C11—C12—H8120.0C45—C46—C47107.5 (5)
C13—C12—H8120.0C45—C46—C53116.4 (4)
C12—C13—C14120.0 (3)C45—C46—H42106.2
C12—C13—H9120.0C47—C46—C53113.6 (3)
C14—C13—H9120.0C47—C46—H42106.4
C13—C14—C15120.0 (4)C53—C46—H42106.1
C13—C14—H10120.0C46—C47—C48120.0 (4)
C15—C14—H10120.0C46—C47—C52120.0 (4)
C10—C15—C14120.0 (3)C48—C47—C52120.0 (4)
C10—C15—H11120.0C47—C48—C49120.0 (4)
C14—C15—H11120.0C47—C48—H43120.0
N3—C16—C17113.0 (4)C49—C48—H43120.0
N3—C16—H14108.6C48—C49—C50120.0 (5)
N3—C16—H15108.5C48—C49—H44119.9
C17—C16—H14108.7C50—C49—H44120.1
C17—C16—H15108.6C49—C50—C51120.0 (4)
H14—C16—H15109.4C49—C50—H45119.9
C16—C17—C18112.0 (4)C51—C50—H45120.1
C16—C17—C24111.3 (4)C50—C51—C52120.0 (4)
C16—C17—H16106.7C50—C51—H46119.9
C18—C17—C24112.9 (3)C52—C51—H46120.1
C18—C17—H16106.7C47—C52—C51120.0 (4)
C24—C17—H16106.8C47—C52—H47120.0
C17—C18—C19117.7 (4)C51—C52—H47120.0
C17—C18—C23122.3 (3)C46—C53—C54117.9 (4)
C19—C18—C23120.0 (3)C46—C53—C58122.0 (3)
C18—C19—C20120.0 (3)C54—C53—C58120.0 (4)
C18—C19—H17120.0C53—C54—C55120.0 (3)
C20—C19—H17120.0C53—C54—H48120.0
C19—C20—C21120.0 (3)C55—C54—H48120.0
C19—C20—H18120.0C54—C55—C56120.0 (3)
C21—C20—H18120.0C54—C55—H49120.0
C20—C21—C22120.0 (3)C56—C55—H49120.0
C20—C21—H19120.0C55—C56—C57120.0 (4)
C22—C21—H19120.0C55—C56—H50120.0
C21—C22—C23120.0 (4)C57—C56—H50120.0
C21—C22—H20120.0C56—C57—C58120.0 (4)
C23—C22—H20120.0C56—C57—H51120.0
C18—C23—C22120.0 (3)C58—C57—H51120.0
C18—C23—H21120.0C53—C58—C57120.0 (3)
C22—C23—H21120.0C53—C58—H52120.0
C17—C24—C25120.3 (4)C57—C58—H52120.0
Cu1—N1—C1—O117.0 (6)C10—C15—C14—C130.0 (6)
Cu1—N1—C1—N2162.7 (3)C11—C10—C15—C140.0 (6)
Cu1—N1—C2—O220.2 (8)C11—C12—C13—C140.0 (6)
Cu1—N1—C2—C3158.9 (3)C12—C11—C10—C150.0 (6)
Cu1—N3—C16—C17172.7 (3)C12—C13—C14—C150.0 (6)
Cu1—N4—C30—O32.8 (5)C16—C17—C18—C19157.4 (4)
Cu1—N4—C30—N5176.0 (2)C16—C17—C18—C2324.2 (6)
Cu1—N4—C31—O40.3 (6)C16—C17—C24—C2581.9 (4)
Cu1—N4—C31—C32178.9 (2)C16—C17—C24—C2992.9 (4)
Cu1—N6—C45—C46178.1 (4)C17—C18—C19—C20178.5 (4)
O1—C1—N1—C2177.3 (5)C17—C18—C23—C22178.4 (5)
O1—C1—N2—C3179.2 (5)C17—C24—C25—C26174.7 (3)
O2—C2—N1—C1177.2 (5)C17—C24—C29—C28174.8 (3)
O2—C2—C3—N2178.0 (4)C18—C17—C24—C2545.0 (5)
O2—C2—C3—C463.1 (5)C18—C17—C24—C29140.2 (3)
O2—C2—C3—C1064.6 (6)C18—C19—C20—C210.0 (7)
O3—C30—N4—C31176.2 (4)C18—C23—C22—C210.0 (8)
O3—C30—N5—C32172.9 (4)C19—C18—C17—C2476.1 (5)
O4—C31—N4—C30178.6 (4)C19—C18—C23—C220.0 (7)
O4—C31—C32—N5177.0 (4)C19—C20—C21—C220.0 (7)
O4—C31—C32—C3367.8 (5)C20—C19—C18—C230.0 (7)
O4—C31—C32—C3959.0 (5)C20—C21—C22—C230.0 (8)
N1—Cu1—N3—C1678.7 (3)C23—C18—C17—C24102.4 (5)
N1—Cu1—N4—C30122.3 (5)C24—C25—C26—C270.0 (5)
N1—Cu1—N4—C3159.0 (6)C24—C29—C28—C270.0 (5)
N1—Cu1—N6—C4596.1 (3)C25—C24—C29—C280.0 (5)
N1—C1—N2—C31.1 (5)C25—C26—C27—C280.0 (6)
N1—C2—C3—N22.8 (5)C26—C25—C24—C290.0 (5)
N1—C2—C3—C4117.7 (4)C26—C27—C28—C290.0 (6)
N1—C2—C3—C10114.6 (4)C30—N4—C31—C320.0 (4)
N2—C1—N1—C23.1 (5)C30—N5—C32—C317.4 (4)
N2—C3—C4—C592.6 (4)C30—N5—C32—C33111.3 (4)
N2—C3—C4—C980.3 (4)C30—N5—C32—C39123.1 (4)
N2—C3—C10—C11177.8 (4)C31—C32—C33—C341.1 (6)
N2—C3—C10—C156.6 (6)C31—C32—C33—C38179.7 (4)
N3—Cu1—N1—C179.3 (3)C31—C32—C39—C40104.1 (5)
N3—Cu1—N1—C282.0 (4)C31—C32—C39—C4474.1 (5)
N3—Cu1—N4—C30146.0 (3)C32—C33—C34—C35178.6 (4)
N3—Cu1—N4—C3132.7 (3)C32—C33—C38—C37178.7 (4)
N3—C16—C17—C18174.9 (4)C32—C39—C40—C41178.1 (4)
N3—C16—C17—C2457.6 (5)C32—C39—C44—C43178.2 (4)
N4—Cu1—N1—C113.4 (7)C33—C32—C39—C4023.2 (5)
N4—Cu1—N1—C2174.7 (5)C33—C32—C39—C44158.6 (3)
N4—Cu1—N3—C16117.8 (3)C33—C34—C35—C360.0 (7)
N4—Cu1—N6—C4567.5 (3)C33—C38—C37—C360.0 (7)
N4—C30—N5—C328.3 (5)C34—C33—C32—C39126.4 (4)
N4—C31—C32—N54.3 (4)C34—C33—C38—C370.0 (6)
N4—C31—C32—C33110.9 (4)C34—C35—C36—C370.0 (8)
N4—C31—C32—C39122.3 (4)C35—C34—C33—C380.0 (6)
N5—C30—N4—C315.0 (4)C35—C36—C37—C380.0 (8)
N5—C32—C33—C34108.0 (4)C38—C33—C32—C3955.0 (5)
N5—C32—C33—C3870.7 (5)C39—C40—C41—C420.0 (6)
N5—C32—C39—C40146.8 (4)C39—C44—C43—C420.0 (6)
N5—C32—C39—C4435.0 (5)C40—C39—C44—C430.0 (6)
N6—Cu1—N1—C197.7 (3)C40—C41—C42—C430.0 (6)
N6—Cu1—N1—C2101.0 (4)C41—C40—C39—C440.0 (6)
N6—Cu1—N4—C3038.0 (3)C41—C42—C43—C440.0 (6)
N6—Cu1—N4—C31143.3 (3)C45—C46—C47—C4875.4 (5)
N6—C45—C46—C47162.0 (4)C45—C46—C47—C52102.5 (5)
N6—C45—C46—C5369.3 (6)C45—C46—C53—C54164.2 (4)
C1—N1—C2—C33.7 (5)C45—C46—C53—C5819.3 (6)
C1—N2—C3—C21.0 (5)C46—C47—C48—C49177.9 (4)
C1—N2—C3—C4120.0 (4)C46—C47—C52—C51177.9 (4)
C1—N2—C3—C10112.7 (4)C46—C53—C54—C55176.6 (4)
C2—C3—C4—C517.0 (5)C46—C53—C58—C57176.4 (4)
C2—C3—C4—C9170.1 (4)C47—C46—C53—C5470.1 (5)
C2—C3—C10—C1173.5 (5)C47—C46—C53—C58106.4 (4)
C2—C3—C10—C15102.1 (5)C47—C48—C49—C500.0 (6)
C3—C4—C5—C6172.9 (4)C47—C52—C51—C500.0 (6)
C3—C4—C9—C8173.0 (4)C48—C47—C46—C53154.2 (4)
C3—C10—C11—C12175.7 (4)C48—C47—C52—C510.0 (6)
C3—C10—C15—C14175.5 (4)C48—C49—C50—C510.0 (7)
C4—C3—C10—C1153.8 (5)C49—C48—C47—C520.0 (6)
C4—C3—C10—C15130.6 (4)C49—C50—C51—C520.0 (7)
C4—C5—C6—C70.0 (7)C52—C47—C46—C5327.8 (5)
C4—C9—C8—C70.0 (6)C53—C54—C55—C560.0 (6)
C5—C4—C3—C10141.1 (4)C53—C58—C57—C560.0 (6)
C5—C4—C9—C80.0 (6)C54—C53—C58—C570.0 (6)
C5—C6—C7—C80.0 (7)C54—C55—C56—C570.0 (7)
C6—C5—C4—C90.0 (6)C55—C54—C53—C580.0 (6)
C6—C7—C8—C90.0 (7)C55—C56—C57—C580.0 (7)
C9—C4—C3—C1045.9 (5)C55—C56—C57—C580.0 (7)
C10—C11—C12—C130.0 (6)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O4ii0.952.002.915 (6)160
N3—H12···O40.952.172.915 (6)135
N5—H27···O2i0.952.092.857 (5)136
N6—H39···O30.952.072.817 (5)134
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z.

Experimental details

(I)(II)
Crystal data
Chemical formula[Cu(C15H11N2O2)2(C14H15N)2]·2CHCl3[Cu(C15H11N2O2)2(C14H15N)2]
Mr1199.34960.63
Crystal system, space groupOrthorhombic, PbcaTriclinic, P1
Temperature (K)298298
a, b, c (Å)19.37 (1), 29.796 (7), 9.910 (3)14.313 (4), 15.888 (5), 11.863 (4)
α, β, γ (°)90, 90, 9090.13 (3), 95.00 (3), 63.58 (2)
V3)5720 (4)2404.7 (14)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.720.51
Crystal size (mm)0.41 × 0.16 × 0.100.50 × 0.40 × 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, Tmax0.872, 0.9310.783, 0.903
No. of measured, independent and
observed reflections
8516, 6565, 3338 [I > 2σ(I)]12233, 12233, 11075 [I > 0σ(I)]
Rint0.0210.087
(sin θ/λ)max1)0.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.163, 0.99 0.069, 0.161, 0.85
No. of reflections333811075
No. of parameters302527
No. of restraints??
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.460.62, 1.31

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—N12.009 (3)Cu1—N32.005 (3)
N1—Cu1—N389.2 (1)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O1i0.952.022.900 (3)153
N3—H12···O1ii0.952.062.837 (3)137
N3—H13···O20.952.132.922 (3)140
C30—H27···O20.952.573.507 (5)170
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1.
Selected geometric parameters (Å, º) for (II) top
Cu1—O3i2.397 (4)Cu1—N42.026 (4)
Cu1—N11.990 (4)Cu1—N62.032 (4)
Cu1—N32.030 (3)
O3i—Cu1—N1109.8 (1)N1—Cu1—N4163.5 (2)
O3i—Cu1—N392.2 (1)N1—Cu1—N689.1 (2)
O3i—Cu1—N486.7 (1)N3—Cu1—N493.7 (2)
O3i—Cu1—N691.9 (1)N3—Cu1—N6175.0 (2)
N1—Cu1—N386.9 (2)N4—Cu1—N689.2 (2)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O4ii0.952.002.915 (6)160
N3—H12···O40.952.172.915 (6)135
N5—H27···O2i0.952.092.857 (5)136
N6—H39···O30.952.072.817 (5)134
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z.
 

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