Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, [Cu(C15H20N2O4)]n, the copper(II) coordination is square planar. The anionic L-tyrosyl-L-leucinate ligand binds in an N,N',O-tridentate mode to one CuII cation on one side and in an O-monodentate mode to a second CuII cation on the other side, thus defining -Cu-O-C-O-Cu'- chains which run along the a axis. These chains are held together by a strong hydrogen bond involving the hydroxy H atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010500987X/ob1224sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010500987X/ob1224Isup2.hkl
Contains datablock I

CCDC reference: 273031

Comment top

Weak and long non-covalent interactions are important in the structure and function of biological macromolecules (Lippard & Berg, 1994). They contribute to the structure, optimize molecular reactivity, allow molecular recognition, and more. In electron-transfer proteins, these bonds are conveniently tuned to regulate the kinetics of the transfer process, and thus the function of the protein.

The best known and probably most important weak interactions between metal ions, radicals or redox centres are hydrogen bonds (Jeffrey & Saenger, 1991). Real chemical paths are usually a sequence of elemental weak interactions plus strong covalent bonds. They may be identified in protein structures (Perutz, 1993), assigned to a specific biological function (Calvo et al., 2000) and in some cases reproduced in model systems (Costa-Filho et al. 2001, 2004; Santana et al., 2005). Thus, characterization of these weak interactions in model systems is important, and metal compounds with amino acids and peptides are particularly relevant. In previous work (Costa-Filho et al., 2001, 2004; Santana et al., 2005), we characterized the properties of weak interactions between metal ions using electron paramagnetic resonance (EPR) and magnetic measurements. Recently, our work allowed comparison with results obtained in an electron-transfer protein (Calvo et al., 2000; Santana et al., 2005). Both structural and magnetic information about a compound are needed to progress in this direction. In line with the work performed by Costa-Filho et al. (2001, 2004), we are now involved in the study of magnetic interactions in the title compound, (I). So far, our EPR experiments have allowed the evaluation of the exchange interactions transmitted through a 13-step path (two coordination + ten covalent + one hydrogen bond) and which connects CuII ions 9.735 (1) Å apart (see below). Magnetic measurements at very low temperature displayed a magnetic phase transition of the compound, intimately connected to this path. Thus, a detailed structural determination is essential in order to be able to analyze these magnetic data, and this is the scope of the present report.

Fig. 1 presents a molecular view of complex (I). The L-tyrosyl–L-leucine (TyrLeu) ligand binds to atom Cu1 in a tridentate mode via the amino atom N1, the deprotonated peptide atom N2 and the carboxylate atom O3. The square-planar coordination of the metal centre is completed through the binding of the second carboxylate atom O4i [symmetry code: (i) x + 1/2, 1/2 − y, 1 − z] of a neighbouring ligand. This particular coordination leads to CuN2O2 polyhedra mounted onto a 21 screw axis parallel to the a axis, with the CuII cations bridged by carboxylato groups in a –Cu—O—C—O—Cu'- chain sequence. Similar one-dimensional structures have already been described in other Cu–dipeptide complexes [(II) (Nascimento et al., 2001), (III) (Tiliakos et al., 2002) and (IV) (Amirthalingam & Muralidharan, 1976)]. Table 1 presents selected bond distances and angles around the CuII cation in (I), which depart significantly from a regular pattern due to restraints imposed by chelation, a general trend (Cu—Npeptide < Cu—Namine Cu—Ocarbox) which is shared by other dipeptide complexes. There are, however, some distortions which are intrinsic of each structure and which depend on the particular interaction scheme. One of these is the departure from planarity of the CuN2O2 group. The copper coordination plane in (I) presents a slight tetrahedral distortion, with the mean plane through atom Cu1 leaving the donor atoms alternately above and below the mean plane by a mean of 0.10 (1) Å. This value lies somewhere in between the distortions presented in complexes (II) [0.05 (1) Å], (III) [0.12 (1) Å] and (IV) [0.22 (1) Å].

Another distinctive feature is the shape that the two five-membered coordination loops adopt upon chelation. In the present case, the description is simplified by the fact that, in both five-membered loops, four atoms lie very nearly in the same plane, with the fifth one departing significantly and thus giving each ring a well defined `envelope' appearance, viz. in the Cu1/O3/C11/C10/N2 and N2/C9/C8/N1/Cu1 groups, the first four atoms depart by a mean of 0.01 (1) and 0.02 (1) Å from planarity, respectively, while the fifth atom is 0.14 (1) or 0.38 (2) Å away, respectively. An alternative way to evaluate this is through the torsion angles calculated around the loops (Table 1). It can be seen that, in each cycle, one of these torsion angles is distinctly smaller than the rest and corresponds to the quasi-planar part of the cycle.

From the two possible H-donor groups present in the dipeptide (OH and NH2), the first provides a strong intermolecular interaction [O1—H1A···O2(1 − x, y − 1/2, 1/2 − z)], while only one of the amino H atoms appears involved in a fairly weak contact N1—H1C···O3(x + 1/2, 1/2 − y, 1 − z) (Table 2).

In many related compounds where the Cu centre is complexed to dipeptides with aromatic groups in their side chains, some sort of Cu···π interaction has been observed [viz. glycyl-L–leucyl-L-tyrosine (Franks & Van der Helm, 1971), L-tyrosine (Van der Helm & Tatsch, 1972) and glycyl-L-tryptophan (Hursthouse et al., 1971)]. This does not seem to be the case in (I), where the benzene ring is at an angle of 103.5 (1)° to the CuN2O2 mean plane, and the nearest Cu···Carom approach is 3.84 (1) Å. There is, however, a close approach of a methyl H atom to the centroid G of the benzene ring (Table 2).

As already stated, the elemental packing units in the structure are the chains running along the a axis. The synanti carboxylate bridges link symmetry related CuII ions to a nearest-neighbour distance along the chain of 4.981 (1) Å. Fig. 2 presents a simplified view, showing the chain `spine' in bold, as well as two intrachain non-bonding interactions providing the chain stability, namely the weak hydrogen bond involving the amino H atom (full broken lines) and the C—H···π interaction (double broken line).

These `S' shaped strips (Fig. 3) stack parallel to each other, the main link between neighbouring units being the strong hydrogen bond involving the hydroxy group. The bulky lateral wings act as effective chain spacers and, as a result, the second nearest-neighbour distance between cations [Cu1···Cu1(x + 1,y,z) 9.031 (1) Å] is also achieved along the chain and corresponds to one full unit-cell translation along a. The shortest chemical path joining cations from different chains goes through the hydroxy hydrogen bond and links CuII centres 9.735 (1) Å apart via a 19.12 (1) Å path made up of 12 covalent/coordination steps plus one hydrogen bond. We have detected a weak interchain magnetic interaction through this path, of a still unknown character, exhibiting J' (kB) ~0.05 K. This should be compared with the direct link along the chain, Cu1···Cu1(x + 1/2, 1/2 − y, 1 − z), of 4.981 (1) Å, through a four-step path of 6.39 (1) Å, along which a ferromagnetic interaction takes place with J (kB) ~2.5 K.

The way in which chains approach each other favours the appearance of a very short Cu···H contact [Cu1···H14B (1/2 − x, 1 − y, z + 1/2) 2.50 (1) Å, shown as double broken lines in Fig. 3]. A survey of the Cambridge Structural Database (November 2003 update; Allen, 2002) showed this to be a rather infrequent case: out of 4060 reported cases with a CuNnO4-n polyhedra (0< = n < = 4), only 30 presented shorter H···Cu distances, in the range 2.04–2.50 Å.

Experimental top

To a solution containing cupric acetate monohydrate (0.25 mmol) (Merck, Darmstadt, Germany) and L-tyrosyl–L-leucine (0.25 mmol) (Sigma, St Louis, Missouri, USA) in water (20 ml), we added ethanol (20 ml) and 0.1 N NaOH solution (5 ml). After one week, a number of well shaped, though small and extremely poorly diffracting, needles appeared by evaporation of the solution at room temperature.

Refinement top

H atoms attached to C and N atoms were included in calculated positions, with idealized distances to their hosts (C—H = 0.98, C—H2 = 0.97, C—H3 = 0.96, C—Harom = 0.93 and N—H2 = 0.92 Å), and allowed to ride; in the case of terminal CH3, they were allowed to rotate as well. The H atom attached to an O atom was found in the difference density map and refined with a restrained O—H distance of 0.82 (1) Å. In all cases, H atoms were ascribed an isotropic displacement factor Uiso(H) = xUeq(parent), with x = 1.2 for non-methyl H atoms and x = 1.5 for methyl ones.

Computing details top

Data collection: P3/P4-PC (Siemens, 1991); cell refinement: P3/P4-PC; data reduction: XDISK in SHELXTL/PC (Sheldrick, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of (I). The independent part of the molecule is shown in bold and with atom-numbering. Displacement ellipsoids are drawn at the 50% level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) x + 1/2, 1/2 − y, 1 − z.] Please check added symmetry code.
[Figure 2] Fig. 2. A lateral view of a chain, with the main path connecting Cu atoms shown in bold. Full broken lines denote the hydrogen bond involving the amino H atom and double broken lines indicate the C—H···π interactions. [Symmetry code: (i) x + 1/2, 1/2 − y, 1 − z.] Please check added symmetry code.
[Figure 3] Fig. 3. A packing view of (I), down the a axis. For clarity, chains are shown in alternate line weights. Full broken lines denote the hydrogen bond involving the hydroxy H atom, and double broken lines indicate the short H···Cu contact (see text). [Symmetry code: (i) x + 1/2, 1/2 − y, 1 − z.] Please check added symmetry code.
catena-Poly[copper(II)-µ-L-tyrosyl-L-leucinato] top
Crystal data top
[Cu(C15H20N2O4)]F(000) = 740
Mr = 355.87Dx = 1.553 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 9.0307 (9) Åθ = 7.5–12.5°
b = 10.4375 (12) ŵ = 1.45 mm1
c = 16.1471 (18) ÅT = 295 K
V = 1522.0 (3) Å3Needle, blue
Z = 40.55 × 0.14 × 0.12 mm
Data collection top
Siemens R3m
diffractometer
1066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω/2θ scansh = 010
Absorption correction: ψ scan
(SHELXTL/PC; Sheldrick,1994)
k = 012
Tmin = 0.785, Tmax = 0.845l = 019
1662 measured reflections2 standard reflections every 98 reflections
1557 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom+difmap
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0517P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.05
1557 reflectionsΔρmax = 0.32 e Å3
202 parametersΔρmin = 0.36 e Å3
0 restraintsAbsolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (5)
Crystal data top
[Cu(C15H20N2O4)]V = 1522.0 (3) Å3
Mr = 355.87Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.0307 (9) ŵ = 1.45 mm1
b = 10.4375 (12) ÅT = 295 K
c = 16.1471 (18) Å0.55 × 0.14 × 0.12 mm
Data collection top
Siemens R3m
diffractometer
1066 reflections with I > 2σ(I)
Absorption correction: ψ scan
(SHELXTL/PC; Sheldrick,1994)
Rint = 0.055
Tmin = 0.785, Tmax = 0.8452 standard reflections every 98 reflections
1662 measured reflections intensity decay: 2%
1557 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111Δρmax = 0.32 e Å3
S = 1.02Δρmin = 0.36 e Å3
1557 reflectionsAbsolute structure: Flack (1983), no Friedel pairs
202 parametersAbsolute structure parameter: 0.07 (5)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.40970 (10)0.35067 (8)0.49942 (8)0.0315 (3)
O10.6050 (10)0.4465 (6)0.0854 (4)0.059 (2)
H1A0.636 (12)0.370 (4)0.090 (7)0.089*
O20.3197 (7)0.7021 (5)0.4223 (4)0.0414 (16)
O30.2077 (6)0.2797 (4)0.5017 (5)0.0381 (13)
O40.0165 (7)0.3041 (5)0.4511 (4)0.0374 (15)
N10.5822 (7)0.4670 (5)0.4986 (6)0.0482 (17)
H1B0.62220.46980.54970.058*
H1C0.65120.43620.46370.058*
N20.3198 (8)0.4842 (6)0.4387 (4)0.0318 (17)
C10.6188 (10)0.4933 (9)0.1640 (6)0.040 (2)
C20.5624 (11)0.6135 (8)0.1815 (6)0.046 (3)
H2A0.51750.66070.13960.055*
C30.5716 (11)0.6637 (8)0.2594 (5)0.041 (2)
H3A0.53170.74440.26950.049*
C40.6381 (10)0.5984 (8)0.3237 (6)0.040 (2)
C50.7009 (11)0.4791 (9)0.3044 (6)0.048 (3)
H5A0.74970.43320.34560.058*
C60.6916 (11)0.4282 (8)0.2252 (6)0.047 (2)
H6A0.73520.34950.21370.056*
C70.6477 (9)0.6557 (9)0.4098 (5)0.041 (2)
H7A0.62980.74720.40590.049*
H7B0.74770.64410.43040.049*
C80.5399 (10)0.5990 (8)0.4726 (5)0.034 (2)
H8A0.54310.65340.52200.041*
C90.3778 (10)0.5976 (8)0.4415 (5)0.033 (2)
C100.1662 (9)0.4623 (7)0.4151 (5)0.032 (2)
H10A0.10470.53530.43150.038*
C110.1152 (10)0.3401 (9)0.4601 (5)0.033 (2)
C120.1479 (11)0.4352 (8)0.3223 (5)0.038 (2)
H12A0.21440.36600.30750.045*
H12B0.04760.40510.31300.045*
C130.1764 (12)0.5458 (10)0.2646 (6)0.054 (3)
H13A0.27160.58460.27940.064*
C140.1862 (16)0.4958 (14)0.1739 (6)0.099 (5)
H14A0.27970.45380.16560.148*
H14B0.17780.56660.13620.148*
H14C0.10730.43620.16380.148*
C150.0574 (13)0.6476 (11)0.2709 (8)0.083 (4)
H15A0.06150.68700.32450.125*
H15B0.03810.60900.26310.125*
H15C0.07330.71140.22900.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0352 (4)0.0263 (4)0.0330 (4)0.0013 (5)0.0003 (8)0.0057 (7)
O10.100 (6)0.036 (3)0.042 (4)0.008 (4)0.013 (5)0.004 (3)
O20.055 (4)0.024 (3)0.045 (4)0.006 (3)0.001 (3)0.001 (3)
O30.040 (3)0.031 (3)0.044 (3)0.009 (2)0.000 (5)0.013 (5)
O40.034 (3)0.031 (3)0.047 (4)0.002 (3)0.002 (3)0.016 (3)
N10.043 (4)0.034 (3)0.067 (4)0.002 (3)0.019 (7)0.012 (5)
N20.035 (4)0.027 (4)0.033 (4)0.003 (3)0.004 (4)0.008 (3)
C10.039 (6)0.031 (5)0.049 (6)0.007 (5)0.006 (5)0.009 (4)
C20.062 (7)0.036 (5)0.040 (5)0.003 (5)0.001 (5)0.011 (4)
C30.058 (6)0.021 (4)0.044 (5)0.001 (5)0.011 (5)0.007 (4)
C40.036 (5)0.030 (4)0.055 (6)0.007 (4)0.014 (5)0.002 (5)
C50.046 (6)0.043 (6)0.054 (6)0.006 (5)0.003 (5)0.002 (5)
C60.055 (6)0.027 (5)0.058 (6)0.013 (5)0.001 (6)0.005 (5)
C70.039 (5)0.035 (5)0.049 (5)0.014 (5)0.008 (4)0.008 (5)
C80.047 (5)0.020 (4)0.035 (5)0.004 (4)0.003 (4)0.003 (3)
C90.044 (6)0.029 (4)0.026 (4)0.006 (4)0.002 (4)0.005 (4)
C100.035 (5)0.022 (4)0.037 (5)0.002 (4)0.008 (4)0.011 (4)
C110.039 (6)0.037 (5)0.023 (4)0.003 (5)0.002 (4)0.001 (4)
C120.051 (5)0.037 (5)0.025 (4)0.003 (5)0.009 (4)0.008 (4)
C130.047 (6)0.058 (7)0.056 (6)0.011 (6)0.014 (5)0.020 (6)
C140.139 (13)0.128 (11)0.028 (6)0.045 (12)0.014 (8)0.025 (8)
C150.077 (9)0.057 (7)0.116 (10)0.005 (8)0.028 (8)0.045 (8)
Geometric parameters (Å, º) top
Cu1—N21.887 (7)C5—C61.388 (13)
Cu1—O4i1.922 (5)C5—H5A0.9300
Cu1—O31.969 (5)C6—H6A0.9300
Cu1—N11.975 (6)C7—C81.525 (11)
O1—C11.365 (11)C7—H7A0.9700
O1—H1A0.85 (4)C7—H7B0.9700
O2—C91.251 (9)C8—C91.547 (12)
O3—C111.244 (10)C8—H8A0.9800
O4—C111.256 (10)C10—C121.533 (11)
O4—Cu1ii1.922 (5)C10—C111.538 (11)
N1—C81.491 (10)C10—H10A0.9800
N1—H1B0.9000C12—C131.505 (11)
N1—H1C0.9000C12—H12A0.9700
N2—C91.295 (10)C12—H12B0.9700
N2—C101.456 (10)C13—C151.515 (14)
C1—C61.368 (12)C13—C141.558 (15)
C1—C21.383 (12)C13—H13A0.9800
C2—C31.366 (12)C14—H14A0.9600
C2—H2A0.9300C14—H14B0.9600
C3—C41.379 (12)C14—H14C0.9600
C3—H3A0.9300C15—H15A0.9600
C4—C51.403 (12)C15—H15B0.9600
C4—C71.517 (12)C15—H15C0.9600
N2—Cu1—O4i170.4 (3)N1—C8—C7112.5 (7)
N2—Cu1—O383.6 (3)N1—C8—C9109.0 (7)
O4i—Cu1—O389.8 (2)C7—C8—C9113.1 (7)
N2—Cu1—N183.2 (3)N1—C8—H8A107.3
O4i—Cu1—N1104.2 (3)C7—C8—H8A107.3
O3—Cu1—N1164.2 (2)C9—C8—H8A107.3
C1—O1—H1A103 (8)O2—C9—N2128.2 (8)
C11—O3—Cu1114.9 (5)O2—C9—C8118.0 (7)
C11—O4—Cu1ii122.1 (6)N2—C9—C8113.8 (7)
C8—N1—Cu1111.6 (5)N2—C10—C12112.9 (7)
C8—N1—H1B109.3N2—C10—C11107.0 (7)
Cu1—N1—H1B109.3C12—C10—C11106.0 (6)
C8—N1—H1C109.3N2—C10—H10A110.3
Cu1—N1—H1C109.3C12—C10—H10A110.3
H1B—N1—H1C108.0C11—C10—H10A110.3
C9—N2—C10122.6 (7)O3—C11—O4123.2 (8)
C9—N2—Cu1118.8 (6)O3—C11—C10118.3 (7)
C10—N2—Cu1115.5 (5)O4—C11—C10118.5 (8)
O1—C1—C6122.5 (8)C13—C12—C10116.4 (7)
O1—C1—C2118.7 (9)C13—C12—H12A108.2
C6—C1—C2118.7 (9)C10—C12—H12A108.2
C3—C2—C1120.9 (9)C13—C12—H12B108.2
C3—C2—H2A119.5C10—C12—H12B108.2
C1—C2—H2A119.5H12A—C12—H12B107.3
C2—C3—C4122.0 (8)C12—C13—C15112.0 (9)
C2—C3—H3A119.0C12—C13—C14109.6 (9)
C4—C3—H3A119.0C15—C13—C14109.8 (10)
C3—C4—C5116.6 (9)C12—C13—H13A108.5
C3—C4—C7121.3 (8)C15—C13—H13A108.5
C5—C4—C7122.0 (9)C14—C13—H13A108.5
C6—C5—C4121.3 (9)C13—C14—H14A109.5
C6—C5—H5A119.4C13—C14—H14B109.5
C4—C5—H5A119.4H14A—C14—H14B109.5
C1—C6—C5120.4 (9)C13—C14—H14C109.5
C1—C6—H6A119.8H14A—C14—H14C109.5
C5—C6—H6A119.8H14B—C14—H14C109.5
C4—C7—C8114.8 (7)C13—C15—H15A109.5
C4—C7—H7A108.6C13—C15—H15B109.5
C8—C7—H7A108.6H15A—C15—H15B109.5
C4—C7—H7B108.6C13—C15—H15C109.5
C8—C7—H7B108.6H15A—C15—H15C109.5
H7A—C7—H7B107.5H15B—C15—H15C109.5
Cu1—N1—C8—C98.6 (8)Cu1—O3—C11—C101.9 (10)
N1—C8—C9—N25.0 (10)O3—C10—C11—N24.2 (10)
C8—C9—N2—Cu117.9 (9)C10—C11—N2—Cu1172.0 (7)
C9—N2—Cu1—N118.7 (7)C11—N2—Cu1—O32.7 (3)
N2—Cu1—N1—C814.0 (6)N2—Cu1—O3—C104.5 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2iii0.85 (4)1.81 (4)2.642 (8)168 (12)
N1—H1C···O3i0.902.382.813 (7)110
C15—H15B···Giv0.963.084.02167
Symmetry codes: (i) x+1/2, y+1/2, z+1; (iii) x+1, y1/2, z+1/2; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formula[Cu(C15H20N2O4)]
Mr355.87
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)9.0307 (9), 10.4375 (12), 16.1471 (18)
V3)1522.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.55 × 0.14 × 0.12
Data collection
DiffractometerSiemens R3m
diffractometer
Absorption correctionψ scan
(SHELXTL/PC; Sheldrick,1994)
Tmin, Tmax0.785, 0.845
No. of measured, independent and
observed [I > 2σ(I)] reflections
1662, 1557, 1066
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.111, 1.02
No. of reflections1557
No. of parameters202
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.36
Absolute structureFlack (1983), no Friedel pairs
Absolute structure parameter0.07 (5)

Computer programs: P3/P4-PC (Siemens, 1991), P3/P4-PC, XDISK in SHELXTL/PC (Sheldrick, 1994), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC, SHELXL97.

Selected geometric parameters (Å, º) top
Cu1—N21.887 (7)Cu1—O31.969 (5)
Cu1—O4i1.922 (5)Cu1—N11.975 (6)
N2—Cu1—O4i170.4 (3)N2—Cu1—N183.2 (3)
N2—Cu1—O383.6 (3)O4i—Cu1—N1104.2 (3)
O4i—Cu1—O389.8 (2)O3—Cu1—N1164.2 (2)
Cu1—N1—C8—C98.6 (8)Cu1—O3—C11—C101.9 (10)
N1—C8—C9—N25.0 (10)O3—C10—C11—N24.2 (10)
C8—C9—N2—Cu117.9 (9)C10—C11—N2—Cu1172.0 (7)
C9—N2—Cu1—N118.7 (7)C11—N2—Cu1—O32.7 (3)
N2—Cu1—N1—C814.0 (6)N2—Cu1—O3—C104.5 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2ii0.85 (4)1.81 (4)2.642 (8)168 (12)
N1—H1C···O3i0.902.382.813 (7)110
C15—H15B···Giii0.963.084.02167
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y1/2, z+1/2; (iii) x1, y, z.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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