metal-organic papers
m670
Mac-Leod-Careyet al. [Cu(C12H13N2O3)2] doi:10.1107/S1600536806053396 Acta Cryst.(2007). E63, m670–m672
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Bis[2-(2,4-dioxopentan-3-ylidene-j
O
)-1-(4-methoxy-phenyl)hydrazinato-j
N
1]copper(II)
Desmond A. Mac-Leod-Carey,a
Carlos Bustos,bEduardo Schott,b
Luis Alvarez-Thonc* and
Mauricio Fuentealbad
aFacultad de Quı´mica, Departamento de Quı´mica Inorga´nica, Pontificia Universidad Cato´lica de Chile, Avenida Vicun˜a Mackenna 4860, Casilla 306, Macul, Santiago de Chile, Chile,bInstituto de Quı´mica, Universidad Austral de Chile, Avenida Los Robles s/n, Campus Isla Teja, Casilla 567, Valdivia, Chile, cDepartamento de Ciencias Quı´micas, Universidad Andre´s Bello, Repu´blica 275, Santiago de Chile, Chile, anddCIMAT, Departamento de Cristalografı´a, Facultad de Ciencias Fı´sicas y Matema´ticas, Universidad de Chile, Casilla 487-3, Santiago de Chile, Chile
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 298 K
Mean(C–C) = 0.003 A˚
Rfactor = 0.045
wRfactor = 0.122
Data-to-parameter ratio = 16.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 17 November 2006 Accepted 10 December 2006
#2007 International Union of Crystallography All rights reserved
Molecules in the title compound, [Cu(C12H13N2O3)2], are
linkedviaweak C—H O and C—H (arene) interactions into a three-dimensional network. The Cu atom lies on an inversion centre, and therefore the asymmetric unit contains half a formula unit. The coordination geometry about the Cu atom can be described as tetragonally distorted octahedral.
Comment
Copper complexes containing Schiff bases have important applications, e.g. as a mimetic peroxidase in the catalytic oxidation of phenol by H2O2(Liet al., 2004) or as a source of
cross-linking in polymers that contain a Schiff base at the side chain (Campilloset al., 1996). On the other hand, we have used -diketohydrazones of the type (CH3CO)2C NNHC6H4-R
(Yao, 1964) for obtaining organic functions as isoxazoles (Alvarez-Thonet al., 2006) and pyrazoles (Bustoset al., 2006). The title compound represents a case where the -diketohy-drazone ligands or its derivatives can be used as metal extracting agents.
The molecular structure of the title compound, (I), is shown in Fig. 1. The Cu atom lies on an inversion centre and there-fore the asymmetric unit contains half a formula unit. Despite the long Cu—O2i distance [2.866 (2) A˚ ; symmetry code: (i)
1 2+x,
1
2y, 1z], the coordination geometry about the Cu
Atoms O1, C1, C2, N1, N2, C3 and C4 are essentially coplanar (r.m.s. deviation = 0.002 A˚ for all atoms), while the Cu atom deviates by 0.51 A˚ from this plane.
There are no conventional intermolecular hydrogen bonds in (I) and the entire supramolecular structure is constructed only by weak interactions. For the sake of clarity, the crystal packing can be described as a combination of two types of
interactions, namely weak C7—H7 O2i and C5—
H5A O1iiinteractions (Fig. 2) and C12—H12A (arene)iii interactions (Maloneet al., 1997), which further stabilize the structure (Fig. 3) and where the distance from atom H12Ato the centroid of the C6–C9 ring at (1x,1
2+y, 1
2z) is 2.93 A˚ ,
which is short enough (less than 3.05 A˚ ; see Malone et al., 1997) for this interaction to be considered significant. (All symmetry codes are as given in Table 2 and in Figs. 2 and 3).
Experimental
Copper(II) acetate monohydrate, Cu(OAc)2H2O (2.0 mmol, 0.40 g),
2-(2,4-dioxopentan-3-ylidene)-1-(4-methoxyphenyl)hydrazin-1-ide {deprotonated form of 3-[2-(4-methoxyphenyl)hydrazono]pentane-2,4-dione; 4.26 mmol, 1.00 g} and ethanol (10 ml), were added to a 100 ml round-bottomed flask connected to a reflux condenser. The mixture was stirred and gently heated under reflux until a dark solid appeared. The insoluble material was filtered off by suction and dried under vacuum. The solid was purified by extraction in a Soxhlet apparatus using acetone as solvent. The microcrystalline plates which formed were filtered off and washed with acetone. Single crystals of (I) suitable for diffraction studies were obtained by diffusion of methanol into a concentrated solution containing 15 mg of the purified complex in 5 ml of anhydrous dimethyl sulfoxide (crude yield: 90%).
Crystal data
[Cu(C12H13N2O3)2]
Mr= 530.04
Orthorhombic,Pbca a= 13.6125 (17) A˚ b= 7.5417 (9) A˚ c= 23.135 (3) A˚ V= 2375.1 (5) A˚3
Z= 4
Dx= 1.482 Mg m
3
MoKradiation = 0.97 mm1
T= 298 K Block, dark red 0.410.260.21 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan [SADABS(Sheldrick, 1996) in SAINT(Bruker, 2000)] Tmin= 0.678,Tmax= 0.816
16264 measured reflections 2743 independent reflections 1979 reflections withI> 2(I) Rint= 0.040
max= 28.0
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.045 wR(F2) = 0.122
S= 1.09 2743 reflections 163 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0621P)2
+ 0.589P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.47 e A˚
3
min=0.19 e A˚
3
metal-organic papers
Acta Cryst.(2007). E63, m670–m672 Mac-Leod-Careyet al. [Cu(C
[image:2.610.47.295.72.266.2]12H13N2O3)2]
m671
Figure 1
The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Part of the crystal structure of (I), showing the formation of two weak C— H O contacts. H atoms not involved in these interactions (dotted lines) have been omitted. [Symmetry codes: (i)x+1
2,y+ 1
2,z+ 1; (ii)x 1 2, 1
[image:2.610.314.561.72.158.2]2y,z+ 1].
Figure 3
Detail of the C—H (arene) interactions that further stabilize (I). The dotted lines represent the vectors between H atoms and the ring centroids. [Symmetry code: (iii) 1x,1
[image:2.610.46.294.323.535.2]Table 1
Selected geometric parameters (A˚ ,).
Cu1—O1 1.9164 (14)
Cu1—N1 1.9855 (18)
Cu1—O2i 2.866 (2)
O1—C2 1.264 (3)
N1—N2 1.279 (2)
N2—C1 1.357 (3)
O1—Cu1—N1 88.05 (7)
O1—Cu1—O2i 98.36 (6)
O2i
—Cu1—N1 94.26 (7)
Cu1—O1—C2 128.68 (14)
Cu1—N1—N2 124.88 (14)
Cu1—N1—C6 124.97 (14)
N1—N2—C1 125.02 (18)
N2—C1—C2 124.53 (19)
N2—C1—C4 110.74 (18)
C2—C1—C4 124.46 (19)
O1—C2—C1 122.00 (19)
O1—C2—C3 114.97 (19)
C1—C2—C3 123.0 (2)
Symmetry code: (i)xþ1 2;yþ
1 2;zþ1.
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
C7—H7 O2i
0.93 2.55 3.426 (3) 158
C5—H5A O1ii
0.96 2.55 3.363 (3) 142
Symmetry codes: (i)xþ1 2;yþ
1
2;zþ1; (ii)x 1 2;yþ
1 2;zþ1.
H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with aromatic C—H = 0.93 A˚ and Uiso(H) = 1.2 Ueq(C), and methyl C—H = 0.96 A˚ and
Uiso(H) = 1.5Ueq(C). The methyl groups were allowed to rotate but
not to tip.
Data collection:SMART(Bruker, 2001); cell refinement:SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine
structure:SHELXL97(Sheldrick, 1997); molecular graphics:XPin SHELXTL/PC(Sheldrick, 1994); software used to prepare material for publication:PLATON(Spek, 2003) andMercury(Macraeet al., 2006).
The authors gratefully acknowledge financial support from Direccio´n de Investigacio´n y Desarrollo of the Universidad Austral de Chile (grant No. S-2006-45) and the Universidad Andre´s Bello (grant No. DI-UNAB 12-04). We also thank CONICYT–FONDAP (grant No. 11980002).
References
Alvarez-Thon, L., Bustos, C., Schott, E., Sanchez, C. & Iban˜ez, A. (2006).Acta Cryst.E62, o595–o597.
Bruker (2000).SAINT. Version 6.02a. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001).SMART. Version 5.624. Bruker AXS Inc., Madison, Wisconsin, USA.
Bustos, C., Schott, E., Mac-Leod-Carey, D. A., Iban˜ez, A. & Alvarez-Thon, L. (2006).Acta Cryst.E62, o2499–o2501.
Campillos, E., Marcos, M., Serrano, J. L., Alonso, P. J. & Martı´nez, J. I. (1996). J. Mater. Chem.6, 533–538.
Li, S.-X., Li, J.-Z., Xie, J.-Q., Chen, Y., Meng, X.-G., Hu, C.-W. & Zeng, X.-C. (2004).Acta Chim. Sinica,62, 567–572.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).J. Appl. Cryst.39, 453–457. Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J.
(1997).J. Chem. Soc. Faraday Trans.93, 3429–3436.
Sheldrick, G. M. (1994).SHELXTL/PC. Version 5.03. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13. Yao, H. C. (1964).J. Org. Chem.29, 2059–2963.
metal-organic papers
m672
Mac-Leod-Careyet al. [Cu(Csupporting information
sup-1 Acta Cryst. (2007). E63, m670–m672
supporting information
Acta Cryst. (2007). E63, m670–m672 [https://doi.org/10.1107/S1600536806053396]
Bis[2-(2,4-dioxopentan-3-ylidene-
κ
O
)-1-(4-methoxyphenyl)hydrazinato-κ
N
1]copper(II)
Desmond A. Mac-Leod-Carey, Carlos Bustos, Eduardo Schott, Luis Alvarez-Thon and Mauricio
Fuentealba
Bis[2-(2,4-dioxopentan-3-ylidene-κO)-1-(4-methoxyphenyl)hydrazinato- κN1]copper(II)
Crystal data
[Cu(C12H13N2O3)2]
Mr = 530.04
Orthorhombic, Pbca
Hall symbol: -P 2ac 2ab
a = 13.6125 (17) Å
b = 7.5417 (9) Å
c = 23.135 (3) Å
V = 2375.1 (5) Å3
Z = 4
F(000) = 1100
Dx = 1.482 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2743 reflections
θ = 2.3–28.0°
µ = 0.97 mm−1
T = 298 K Block, dark red 0.41 × 0.26 × 0.21 mm
Data collection
Bruker SMART CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan
[SADABS (Sheldrick, 1996) in SAINT (Bruker, 2000)]
Tmin = 0.678, Tmax = 0.816
16264 measured reflections
2743 independent reflections 1979 reflections with I > 2σ(I)
Rint = 0.040
θmax = 28.0°, θmin = 2.3°
h = −17→18
k = −9→9
l = −30→29
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.045
wR(F2) = 0.122
S = 1.09 2743 reflections 163 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0621P)2 + 0.589P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.47 e Å−3
supporting information
sup-2 Acta Cryst. (2007). E63, m670–m672
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to
zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant
to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F,
and R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
Cu1 0.50000 0.00000 0.50000 0.0393 (1) O1 0.42398 (10) 0.1371 (2) 0.55351 (6) 0.0428 (5) O2 0.11896 (12) 0.2196 (3) 0.54570 (7) 0.0613 (7) O3 0.41303 (14) −0.0581 (3) 0.20377 (7) 0.0578 (6) N1 0.39297 (13) 0.0336 (3) 0.44273 (8) 0.0379 (6) N2 0.30328 (12) 0.0662 (3) 0.45540 (7) 0.0375 (6) C1 0.27050 (16) 0.1162 (3) 0.50835 (9) 0.0360 (7) C2 0.33182 (16) 0.1564 (3) 0.55578 (9) 0.0375 (7) C3 0.29370 (18) 0.2281 (4) 0.61170 (10) 0.0529 (9) C4 0.16306 (17) 0.1404 (3) 0.50789 (9) 0.0407 (7) C5 0.10739 (17) 0.0661 (4) 0.45772 (11) 0.0493 (8) C6 0.40179 (16) 0.0013 (3) 0.38126 (10) 0.0388 (7) C7 0.48358 (16) 0.0595 (4) 0.35232 (10) 0.0420 (7) C8 0.49043 (17) 0.0413 (4) 0.29254 (11) 0.0464 (8) C9 0.41455 (18) −0.0365 (3) 0.26242 (10) 0.0458 (8) C10 0.33371 (18) −0.1000 (4) 0.29172 (10) 0.0519 (9) C11 0.32709 (17) −0.0817 (4) 0.35071 (9) 0.0477 (8) C12 0.4951 (2) 0.0024 (4) 0.17215 (14) 0.0642 (11) H3A 0.34190 0.21070 0.64140 0.0790* H3B 0.23430 0.16720 0.62200 0.0790* H3C 0.28040 0.35250 0.60760 0.0790* H5A 0.03960 0.10010 0.46060 0.0740* H5B 0.11240 −0.06080 0.45800 0.0740* H5C 0.13450 0.11140 0.42240 0.0740* H7 0.53490 0.11140 0.37280 0.0500* H8 0.54590 0.08160 0.27310 0.0560* H10 0.28330 −0.15550 0.27150 0.0620* H11 0.27240 −0.12510 0.37020 0.0570* H12A 0.50140 0.12830 0.17680 0.0960* H12B 0.48630 −0.02520 0.13200 0.0960* H12C 0.55340 −0.05490 0.18620 0.0960*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
supporting information
sup-3 Acta Cryst. (2007). E63, m670–m672
O1 0.0315 (8) 0.0591 (10) 0.0378 (8) 0.0024 (7) −0.0023 (6) −0.0104 (7) O2 0.0397 (9) 0.0913 (15) 0.0528 (10) 0.0092 (9) 0.0066 (8) −0.0208 (10) O3 0.0657 (12) 0.0778 (12) 0.0299 (9) −0.0027 (10) 0.0025 (8) −0.0024 (8) N1 0.0308 (10) 0.0518 (11) 0.0312 (9) 0.0021 (8) −0.0004 (8) −0.0022 (8) N2 0.0310 (9) 0.0470 (10) 0.0344 (10) 0.0007 (8) 0.0003 (7) −0.0001 (8) C1 0.0316 (11) 0.0432 (12) 0.0331 (11) 0.0023 (9) 0.0020 (8) −0.0017 (9) C2 0.0368 (11) 0.0400 (12) 0.0357 (11) −0.0001 (9) 0.0043 (9) −0.0003 (9) C3 0.0480 (14) 0.0694 (17) 0.0414 (13) 0.0056 (12) 0.0006 (11) −0.0162 (12) C4 0.0341 (12) 0.0490 (13) 0.0389 (12) 0.0038 (10) 0.0022 (9) −0.0007 (10) C5 0.0335 (12) 0.0654 (16) 0.0490 (14) 0.0033 (11) −0.0021 (10) −0.0029 (13) C6 0.0351 (11) 0.0506 (13) 0.0306 (11) 0.0054 (9) −0.0015 (9) −0.0020 (9) C7 0.0389 (12) 0.0522 (13) 0.0350 (12) −0.0030 (10) 0.0012 (9) −0.0015 (11) C8 0.0464 (15) 0.0564 (15) 0.0364 (13) −0.0027 (11) 0.0054 (10) 0.0043 (11) C9 0.0522 (14) 0.0537 (14) 0.0314 (12) 0.0058 (11) −0.0011 (10) −0.0020 (10) C10 0.0435 (14) 0.0739 (18) 0.0384 (12) −0.0053 (12) −0.0026 (11) −0.0105 (12) C11 0.0371 (12) 0.0700 (17) 0.0361 (12) −0.0061 (11) 0.0012 (10) −0.0054 (12) C12 0.080 (2) 0.075 (2) 0.0375 (15) −0.0070 (15) 0.0137 (13) 0.0025 (12)
Geometric parameters (Å, º)
Cu1—O1 1.9164 (14) C6—C11 1.388 (3) Cu1—N1 1.9855 (18) C7—C8 1.393 (3) Cu1—O2i 2.866 (2) C8—C9 1.377 (3)
Cu1—O1ii 1.9164 (14) C9—C10 1.378 (3)
Cu1—N1ii 1.9855 (18) C10—C11 1.375 (3)
Cu1—O2iii 2.866 (2) C3—H3A 0.9600
O1—C2 1.264 (3) C3—H3B 0.9600 O2—C4 1.218 (3) C3—H3C 0.9600 O3—C9 1.367 (3) C5—H5A 0.9600 O3—C12 1.411 (3) C5—H5B 0.9600 N1—N2 1.279 (2) C5—H5C 0.9600 N1—C6 1.448 (3) C7—H7 0.9300 N2—C1 1.357 (3) C8—H8 0.9300 C1—C2 1.412 (3) C10—H10 0.9300 C1—C4 1.474 (3) C11—H11 0.9300 C2—C3 1.495 (3) C12—H12A 0.9600 C4—C5 1.495 (3) C12—H12B 0.9600 C6—C7 1.371 (3) C12—H12C 0.9600
Cu1···O2i 2.866 (2) C5···H12Bix 2.7400
Cu1···O2iii 2.866 (2) C5···H5Axii 3.0200
Cu1···H7 3.1000 C7···H12Cx 3.0800
Cu1···H5Ai 3.2000 C8···H12A 2.7600
Cu1···H7ii 3.1000 C8···H12C 2.7000
Cu1···H5Aiii 3.2000 C9···H8vi 3.0400
O1···N1 2.712 (2) C11···H5Ciii 2.9000
supporting information
sup-4 Acta Cryst. (2007). E63, m670–m672
O1···C7ii 2.920 (3) C12···H3Axiii 3.0900
O1···N1ii 2.806 (2) H3A···C12xiv 3.0900
O1···C6ii 2.999 (3) H3B···O2 2.4000
O1···O2iii 3.208 (3) H3B···C4 2.8200
O2···C2iv 3.370 (3) H3B···O3vii 2.8800
O2···Cu1v 2.866 (2) H3B···H3Ciii 2.4000
O2···C3 2.827 (3) H3C···O2 2.8100 O2···O1iv 3.208 (3) H3C···C2iv 3.0000
O2···Cu1v 2.866 (2) H3C···C3iv 3.0100
O3···C8vi 3.296 (4) H3C···H3Biv 2.4000
O1···H7ii 2.5900 H5A···Cu1v 3.2000
O1···H5Ai 2.5500 H5A···O1v 2.5500
O2···H3C 2.8100 H5A···C5xii 3.0200
O2···H7v 2.5500 H5A···H12Bix 2.4500
O2···H3B 2.4000 H5A···Cu1v 3.2000
O2···H12Bvii 2.8600 H5B···N2 2.7700
O3···H3Bviii 2.8800 H5C···N2 2.4400
O3···H8vi 2.8300 H5C···C12ix 3.0100
N1···O1 2.712 (2) H5C···H12Bix 2.5900
N1···C2 2.897 (3) H5C···C11iv 2.9000
N1···O1ii 2.806 (2) H7···Cu1 3.1000
N1···C4iii 3.413 (3) H7···O2i 2.5500
N2···O1 2.853 (2) H7···O1ii 2.5900
N2···H5B 2.7700 H8···C12 2.5100 N2···H5C 2.4400 H8···H12A 2.3400 N2···H11 2.4800 H8···H12C 2.2600 C3···O2 2.827 (3) H8···O3x 2.8300
C5···C12ix 3.405 (4) H8···C9x 3.0400
C5···O1v 3.363 (3) H11···N2 2.4800
C7···C12x 3.400 (4) H12A···C8 2.7600
C7···O1ii 2.920 (3) H12A···H8 2.3400
C8···C12x 3.578 (4) H12B···O2viii 2.8600
C8···O3x 3.296 (4) H12B···C5xi 2.7400
C12···C5xi 3.405 (4) H12B···H5Axi 2.4500
C12···C8vi 3.578 (4) H12B···H5Cxi 2.5900
C12···C7vi 3.400 (4) H12C···C8 2.7000
C2···H3Ciii 3.0000 H12C···H8 2.2600
C3···H3Ciii 3.0100 H12C···C7vi 3.0800
C4···H3B 2.8200
O1—Cu1—N1 88.05 (7) C6—C7—C8 120.5 (2) O1—Cu1—O2i 98.36 (6) C7—C8—C9 119.6 (2)
O1—Cu1—O1ii 180.00 O3—C9—C8 124.4 (2)
O1—Cu1—N1ii 91.95 (7) O3—C9—C10 115.8 (2)
O1—Cu1—O2iii 81.64 (6) C8—C9—C10 119.9 (2)
O2i—Cu1—N1 94.26 (7) C9—C10—C11 120.4 (2)
O1ii—Cu1—N1 91.95 (7) C6—C11—C10 120.2 (2)
supporting information
sup-5 Acta Cryst. (2007). E63, m670–m672
O2iii—Cu1—N1 85.74 (7) C2—C3—H3B 110.00
O1ii—Cu1—O2i 81.64 (6) C2—C3—H3C 109.00
O2i—Cu1—N1ii 85.74 (7) H3A—C3—H3B 109.00
O2i—Cu1—O2iii 180.00 H3A—C3—H3C 109.00
O1ii—Cu1—N1ii 88.05 (7) H3B—C3—H3C 109.00
O1ii—Cu1—O2iii 98.36 (6) C4—C5—H5A 109.00
O2iii—Cu1—N1ii 94.26 (7) C4—C5—H5B 109.00
Cu1—O1—C2 128.68 (14) C4—C5—H5C 109.00 Cu1v—O2—C4 112.06 (14) H5A—C5—H5B 110.00
C9—O3—C12 117.7 (2) H5A—C5—H5C 109.00 Cu1—N1—N2 124.88 (14) H5B—C5—H5C 109.00 Cu1—N1—C6 124.97 (14) C6—C7—H7 120.00 N2—N1—C6 109.66 (17) C8—C7—H7 120.00 N1—N2—C1 125.02 (18) C7—C8—H8 120.00 N2—C1—C2 124.53 (19) C9—C8—H8 120.00 N2—C1—C4 110.74 (18) C9—C10—H10 120.00 C2—C1—C4 124.46 (19) C11—C10—H10 120.00 O1—C2—C1 122.00 (19) C6—C11—H11 120.00 O1—C2—C3 114.97 (19) C10—C11—H11 120.00 C1—C2—C3 123.0 (2) O3—C12—H12A 109.00 O2—C4—C1 123.0 (2) O3—C12—H12B 109.00 O2—C4—C5 119.5 (2) O3—C12—H12C 109.00 C1—C4—C5 117.53 (19) H12A—C12—H12B 110.00 N1—C6—C7 119.5 (2) H12A—C12—H12C 109.00 N1—C6—C11 121.03 (19) H12B—C12—H12C 109.00 C7—C6—C11 119.4 (2)
N1—Cu1—O1—C2 27.20 (18) N2—N1—C6—C7 143.6 (2) O2i—Cu1—O1—C2 121.22 (18) N2—N1—C6—C11 −34.0 (3)
N1ii—Cu1—O1—C2 −152.80 (18) N1—N2—C1—C4 −179.2 (2)
O2iii—Cu1—O1—C2 −58.78 (18) N1—N2—C1—C2 6.5 (4)
O1—Cu1—N1—N2 −24.3 (2) N2—C1—C2—O1 −4.9 (4) O1—Cu1—N1—C6 164.60 (19) N2—C1—C2—C3 173.8 (2) O2i—Cu1—N1—N2 −122.5 (2) C4—C1—C2—O1 −178.3 (2)
O2i—Cu1—N1—C6 66.36 (19) C2—C1—C4—O2 10.2 (4)
O1ii—Cu1—N1—N2 155.7 (2) C2—C1—C4—C5 −171.0 (2)
O1ii—Cu1—N1—C6 −15.40 (19) C4—C1—C2—C3 0.4 (4)
O2iii—Cu1—N1—N2 57.5 (2) N2—C1—C4—O2 −164.0 (2)
O2iii—Cu1—N1—C6 −113.64 (19) N2—C1—C4—C5 14.8 (3)
Cu1—O1—C2—C1 −18.0 (3) N1—C6—C7—C8 −175.3 (2) Cu1—O1—C2—C3 163.26 (16) C11—C6—C7—C8 2.2 (4) Cu1v—O2—C4—C1 125.40 (19) N1—C6—C11—C10 175.4 (2)
Cu1v—O2—C4—C5 −53.4 (3) C7—C6—C11—C10 −2.1 (4)
supporting information
sup-6 Acta Cryst. (2007). E63, m670–m672
Cu1—N1—C6—C7 −44.1 (3) C8—C9—C10—C11 1.8 (4) Cu1—N1—C6—C11 138.3 (2) C9—C10—C11—C6 0.1 (4)
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, z; (iv) −x+1/2, y+1/2, z; (v) x−1/2, −y+1/2, −z+1; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1/2, −y, z+1/2; (viii) −x+1/2, −y, z−1/2; (ix) x−1/2, y, −z+1/2; (x) −x+1, y+1/2, −z+1/2; (xi) x+1/2, y, −z+1/2; (xii) −x, −y, −z+1; (xiii) x, −y+1/2, z−1/2; (xiv) x, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C3—H3B···O2 0.96 2.40 2.827 (3) 107 C7—H7···O2i 0.93 2.55 3.426 (3) 158
C5—H5A···O1v 0.96 2.55 3.363 (3) 142
C7—H7···O1ii 0.93 2.59 2.920 (3) 101
C12—H12A···Cgx 0.96 2.93 3.841 (3) 160
