metal-organic papers
m1310
Yuanet al. [Cu(C14H9N3O4)(C4H9NO)] doi:10.1107/S1600536805017642 Acta Cryst.(2005). E61, m1310–m1312 Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
(Morpholine-
j
N
)(salicylaldehyde
4-nitrobenzoyl-hydrazonato-
j
3O
,
N
,
O
000)copper(II)
Li-Hui Yuan, Qiong-Jie Wu and Shi-Xiong Liu*
Department of Chemistry, Fuzhou University, Fuzhou, Fujian 350002, People’s Republic of China
Correspondence e-mail: shixiongliu@yahoo.com
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C–C) = 0.006 A˚ Disorder in main residue
Rfactor = 0.054
wRfactor = 0.120
Data-to-parameter ratio = 14.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the structure of the title complex, [Cu(C14H9N3O4
)-(C4H9NO)], the Cu atom is coordinated by two O atoms
and one N atom from the N-salicylaldehyde p -nitrobenzoyl-hydrazone ligand and one N atom from a morpholine molecule, forming a square-planar Cu(ONO)(N) coordina-tion. The g factors derived by an electron paramagnetic resonance study are typical for square-planar complexes.
Comment
Hydrazone compounds have been investigated for many years (Mitra et al., 1996; Belicchi-Ferrari et al., 1999). Recently, much attention has been focused on the study of aroyl-hydrazone derivatives with aryl, aroyl and heteroaroyl Schiff bases (Iskander et al., 2001; Cariati et al., 2002), because of their ability to form polynuclear complexes through the additional O-donor atom from the carbonyl group (Singh, 1992; Liu et al., 2003). As part of our systematic research on new aroylhydrazone complexes, we report here the synthesis and characterization of the title copper(II) complex, (I), with theN-salicylaldehyde-p-nitrobenzoylhydrazone ligand (Wu & Liu, 2004).
The CuIIatom in complex (I) (Fig. 1) has a square-planar coordination (Khandar & Nejati, 2000; Adamset al., 1998; Lu
et al., 2003; Chan et al., 1995). The tridentate ligand coordi-nates to the CuIIatomviathe enolate O, the imine N and the deprotonated amide O atoms, forming one five-membered chelate ring (Cu/N1/N2/C8/O2) and one six-membered chelate ring (Cu/N1/C7/C2/C1/O1) (Ruiz-Perez et al., 1997). There is no significant deviation of the metal centre from the N2O2coordination plane, which shows a small but significant
tetrahedral distortion [maximum displacements from the least-squares plane are0.066 (3) and 0.046 (3) A˚ for atoms N1 and O2, respectively], as indicated by the deviations of the bond angles around Cu from the values expected for a regular square-planar geometry (Table 1). Such distortion is often observed in CuII complexes of tridentate chelating agents (Westet al., 1993; Aliet al., 1996, 2001). The Cu—O and Cu—
N bond lengths (Table 1) are in agreement with those found in analogous aroylhydrazone copper complexes (Cheng et al., 1996; Ruiz-Perezet al., 1997; Cariatiet al., 2002).
The electron paramagnetic resonance spectrum of (I) is quasi-isotropic and asymmetric. The values of the g factors (g? = 2.180 and gk = 2.047) are typical for square-planar compounds (Davidet al., 2001; Sulekh & Rajiv, 2005).
Experimental
All reagents were of analytical grade, available commercially and used without further purification. p-Nitrobenzoic ethyl ester and
p-nitrobenzoylhydrazine were prepared following the published procedure of Huang et al. (1997). The ligand was prepared by condensing 1 equivalent of salicylaldehyde and 1 equivalent of the correspondingp-nitrobenzoylhydrazine in ethanol (87.5% yield). The title compound was obtained by dissolving salicylaldehyde-p -nitro-benzoylhydrazone (0.0165 g, 0.05 mmol) in a mixture of dimethyl-formamide (2 ml) and methanol (6 ml), and adding a methanol solution (4 ml) containing CuCl22H2O (0.0170 g, 0.1 mmol) dropwise
to the mixture. After 10 min, ten drops of morpholine were added. The mixture was then stirred at room temperature for 1 h and filtered. Blue block-shaped crystals of (I) formed upon slow evaporation of the filtrate over a period of two weeks.
Crystal data
[Cu(C14H9N3O4)(C4H9NO)]
Mr= 433.90
Monoclinic,C2=c a= 15.054 (7) A˚
b= 6.538 (3) A˚
c= 36.230 (15) A˚
= 95.800 (6) V= 3548 (3) A˚3
Z= 8
Dx= 1.625 Mg m
3 MoKradiation Cell parameters from 3892
reflections
= 2.3–27.2 = 1.27 mm1
T= 293 (2) K Block, blue
0.100.080.05 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin= 0.885,Tmax= 0.938 8552 measured reflections
3892 independent reflections 2581 reflections withI> 2(I)
Rint= 0.044
max= 27.2
h=18!19
k=8!8
l=46!34
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.054
wR(F2) = 0.120
S= 1.04 3892 reflections 272 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2
(Fo2) + (0.0497P)2 + 1.9541P]
whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001
max= 0.44 e A˚ 3
[image:2.610.42.290.70.221.2]min=0.38 e A˚ 3
Table 1
Selected geometric parameters (A˚ ,).
Cu1—O1 1.886 (2)
Cu1—O2 1.923 (3)
Cu1—N1 1.924 (3)
Cu1—N4 2.019 (3)
O1—C1 1.312 (4)
O2—C8 1.296 (4)
O5—C17 1.414 (5)
O5—C16 1.414 (5)
N1—C7 1.279 (5)
N1—N2 1.406 (4)
N2—C8 1.294 (5)
N3—C12 1.456 (5)
N4—C15 1.470 (5)
N4—C18 1.477 (4)
O1—Cu1—O2 173.66 (10) O1—Cu1—N1 93.38 (12) O2—Cu1—N1 81.24 (12) O1—Cu1—N4 92.24 (11) O2—Cu1—N4 93.30 (11) N1—Cu1—N4 173.77 (12) C1—O1—Cu1 127.1 (2) C8—O2—Cu1 110.3 (2) C17—O5—C16 110.1 (3) C7—N1—N2 117.8 (3) C7—N1—Cu1 127.4 (3) N2—N1—Cu1 114.6 (2) C8—N2—N1 108.4 (3) O3B—N3—O4B 124.3 (16) O3B—N3—C12 118.7 (12)
O4B—N3—C12 116.8 (11) C15—N4—C18 108.9 (3) C15—N4—Cu1 116.0 (2) C18—N4—Cu1 114.5 (2) O1—C1—C6 118.6 (3) O1—C1—C2 124.7 (3) N1—C7—C2 124.7 (3) N2—C8—O2 125.4 (4) N2—C8—C9 118.4 (3) O2—C8—C9 116.1 (3) C13—C12—N3 118.7 (4) C11—C12—N3 119.5 (3) N4—C15—C16 112.6 (3) O5—C16—C15 112.1 (4) O5—C17—C18 111.6 (3)
All H atoms were placed in idealized positions (aromatic C—H = 0.93 A˚ , methine C—H = 0.93 A˚, morpholine C—H = 0.97 A˚ and N— H = 0.91 A˚ ) and refined using a riding model, with Uiso (H) =
1.5Ueq(C); the isotropic displacement parameter of the H atom
attached to N4 was allowed to vary freely. Atoms O3 and O4 of the nitro group are disordered over two positions; the final occupancy factors for the disordered atoms are both 0.5.
Data collection:SMART(Bruker, 1996); cell refinement:SAINT
(Bruker, 1994); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 2000); software used to prepare material for publication:SHELXTL.
The authors are grateful for financial support from the National Natural Science Foundation of China (grant Nos. 20431010 and 20171012).
References
Adams, H., Bucknall, R. M., Fenton, D. E., Garcia, M. & Oakes, J. (1998).
Polyhedron,17, 4169–4177.
Ali, M. A., Dey, K. K., Nazimuddin, M., Butcher, R. J., Smith, F. E., Jasinski, J. P. & Jasinski, J. M. (1996).Polyhedron,15, 3331–3339.
Ali, M. A., Mirza, A. H. & Butcher, R. J. (2001).Polyhedron,20, 1037–1043. Belicchi-Ferrari, M., Capacchi, S., Pelosi., G., Reffo, G., Tarasconi, P., Albertini, R., Pinelli, S. & Lunghi, P. (1999).Inorg. Chim. Acta,286, 134– 141.
metal-organic papers
Acta Cryst.(2005). E61, m1310–m1312 Yuanet al. [Cu(C
[image:2.610.312.565.220.429.2]14H9N3O4)(C4H9NO)]
m1311
Figure 1
Bruker (2000). SADABS (Version 2.03), SAINT (Version 6.01), SMART
(Version 5.625) andSHELXTL(Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Cariati, F., Caruso, U., Centore, R., Marcolli, W., De Maria, A., Panunzi, B., Roviello, A. & Tuzi, A. (2002).Inorg. Chem.41, 6597–6603.
Chan, S. C., Koh, L. L., Leung, P. -H., Ranford, J. D. & Sim, K. Y. (1995).Inorg. Chim. Acta,236, 101–108.
Cheng, P., Liao, D.-Z., Yan, S.-P., Jiang, Z.-H., Wang, G.-l., Yao, X.-K. & Wang, H.-G. (1996).Inorg. Chim. Acta,248, 135.–137.
David, L., Cra˘ciun, C., Cozar, O., Chis¸, V., Agut, C., Rusu, D. & Rusu, M. (2001).J. Mol. Struct.563–564, 573–578.
Huang, R. Q., Wang, H. L. & Zhou, J. (1997).The Preparation of Organic Intermediation, pp. 78, 109. Beijing: Chemistry Technical Pubishing Company.
Iskander, M. F., Khalil, T. E., Haase, W., Werner, R., Svoboda, I. & Fuess, H. (2001).Polyhedron,20, 2787–2798.
Khandar, A. A. & Nejati, K. (2000).Polyhedron,19, 607–613.
Liu, L., Ji, Y.-L., Jia, D.-Z. & Yu, K.-B. (2003).Chin. J. Struct. Chem.22, 568– 572.
Lu, W.-G., Feng, X.-L., Liu, H.-W. & Wang, S.-L. (2003).Chin. J. Inorg. Chem. 19, 206–210.
Mitra, A., Banerjee, T., Roychowdhury, P., Saha, N. & Das, S. (1996).
Polyhedron,15, 3371–3375.
Ruiz-Perez, C., Gonzalez-Platas, J., Lotter, H., Lezama, L., Solans, X., Dominguez, S., Martin-Zarza, P., Rocio, M. L., Palacios, M. S. & Gili, P. (1997).Inorg. Chim. Acta,255, 139–148.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Singh, G. (1992). Synth. React. Inorg. Met.-Org. Chem. 22, 1605– 1618.
Sulekh, C. & Rajiv, K. (2005).Spectrochim. Acta A,61, 437–446.
West, D. X., Gebremedhin, H., Butcher, R. J., Jasinski, J. P. & Liberta, A. E. (1993).Polyhedron,12, 2489–2497.
Wu, Q.-J. & Liu, S.-X. (2004).Chin. J. Inorg. Chem.110, 1179–1181.
metal-organic papers
m1312
Yuanet al. [Cu(Csupporting information
sup-1 Acta Cryst. (2005). E61, m1310–m1312
supporting information
Acta Cryst. (2005). E61, m1310–m1312 [https://doi.org/10.1107/S1600536805017642]
(Morpholine-
κ
N
)(salicylaldehyde
4-nitrobenzoylhydrazonato-κ
3O
,
N
,
O
′
)copper(II)
Li-Hui Yuan, Qiong-Jie Wu and Shi-Xiong Liu
(N-Salicylaldehyde-p-nitrobenzoylhydrazonato-κ3O,N,O′) (morpholine-κN)copper(II)
Crystal data
[Cu(C14H9N3O4)(C4H9NO)]
Mr = 433.90 Monoclinic, C2/c
Hall symbol: -C 2yc
a = 15.054 (7) Å
b = 6.538 (3) Å
c = 36.230 (15) Å
β = 95.800 (6)°
V = 3548 (3) Å3
Z = 8
F(000) = 1784
Dx = 1.625 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3892 reflections
θ = 2.3–27.2°
µ = 1.27 mm−1
T = 293 K Needle, blue
0.10 × 0.08 × 0.05 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin = 0.885, Tmax = 0.938
8552 measured reflections 3892 independent reflections 2581 reflections with I > 2σ(I)
Rint = 0.044
θmax = 27.2°, θmin = 2.3°
h = −18→19
k = −8→8
l = −46→34
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.054
wR(F2) = 0.120
S = 1.04 3892 reflections 272 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 atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0497P)2 + 1.9541P] where P = (Fo2 + 2Fc2)/3
supporting information
sup-2 Acta Cryst. (2005). E61, m1310–m1312
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
Cu1 0.22389 (3) 0.07069 (7) 0.365297 (12) 0.03771 (16)
O1 0.22101 (16) −0.0999 (4) 0.32320 (7) 0.0426 (6)
O2 0.21382 (17) 0.2334 (4) 0.40890 (7) 0.0470 (7)
O3A 0.1385 (13) 0.738 (3) 0.5661 (6) 0.078 (5) 0.50
O4A 0.047 (2) 0.523 (4) 0.5802 (8) 0.068 (7) 0.50
O3B 0.067 (2) 0.499 (4) 0.5859 (8) 0.074 (8) 0.50
O4B 0.1075 (14) 0.786 (3) 0.5582 (6) 0.065 (4) 0.50
O5 0.46962 (17) 0.4718 (4) 0.33022 (8) 0.0531 (8)
N1 0.1515 (2) −0.1121 (5) 0.39117 (8) 0.0375 (7)
N2 0.1283 (2) −0.0373 (5) 0.42531 (8) 0.0445 (8)
N3 0.0962 (3) 0.5897 (6) 0.55969 (10) 0.0550 (9)
N4 0.30535 (18) 0.2736 (5) 0.34362 (8) 0.0354 (7)
H4N 0.2690 0.3525 0.3278 0.071 (15)*
C1 0.1774 (2) −0.2728 (6) 0.31768 (10) 0.0355 (8)
C2 0.1291 (2) −0.3717 (5) 0.34440 (10) 0.0356 (8)
C3 0.0872 (2) −0.5576 (6) 0.33542 (11) 0.0429 (9)
H3A 0.0562 −0.6217 0.3531 0.052*
C4 0.0897 (2) −0.6498 (6) 0.30170 (11) 0.0454 (10)
H4A 0.0614 −0.7745 0.2965 0.054*
C5 0.1355 (3) −0.5524 (6) 0.27543 (11) 0.0473 (10)
H5A 0.1368 −0.6109 0.2521 0.057*
C6 0.1788 (3) −0.3709 (6) 0.28340 (10) 0.0452 (10)
H6A 0.2101 −0.3109 0.2654 0.054*
C7 0.1180 (2) −0.2832 (6) 0.37965 (10) 0.0420 (9)
H7A 0.0840 −0.3550 0.3954 0.050*
C8 0.1644 (2) 0.1410 (6) 0.43099 (10) 0.0394 (9)
C9 0.1456 (2) 0.2563 (6) 0.46473 (10) 0.0376 (9)
C10 0.0987 (3) 0.1672 (6) 0.49192 (10) 0.0455 (10)
H10A 0.0784 0.0333 0.4889 0.055*
C11 0.0821 (3) 0.2743 (6) 0.52303 (10) 0.0461 (10)
H11A 0.0510 0.2145 0.5411 0.055*
C12 0.1126 (2) 0.4731 (6) 0.52681 (10) 0.0390 (9)
C13 0.1574 (3) 0.5654 (7) 0.50024 (11) 0.0480 (10)
H13A 0.1756 0.7010 0.5029 0.058*
supporting information
sup-3 Acta Cryst. (2005). E61, m1310–m1312
H14A 0.2071 0.5162 0.4520 0.057*
C15 0.3525 (3) 0.4172 (7) 0.37000 (11) 0.0514 (11)
H15A 0.3908 0.3406 0.3882 0.062*
H15B 0.3091 0.4903 0.3831 0.062*
C16 0.4079 (3) 0.5684 (7) 0.35146 (12) 0.0569 (12)
H16A 0.3689 0.6560 0.3354 0.068*
H16B 0.4400 0.6540 0.3702 0.068*
C17 0.4242 (3) 0.3434 (7) 0.30314 (11) 0.0527 (11)
H17A 0.4673 0.2780 0.2888 0.063*
H17B 0.3847 0.4256 0.2863 0.063*
C18 0.3703 (3) 0.1813 (6) 0.32060 (11) 0.0461 (10)
H18A 0.3387 0.0988 0.3012 0.055*
H18B 0.4103 0.0922 0.3359 0.055*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Cu1 0.0403 (3) 0.0365 (3) 0.0380 (3) −0.0084 (2) 0.01202 (18) −0.0020 (2) O1 0.0536 (16) 0.0358 (16) 0.0413 (15) −0.0165 (12) 0.0183 (12) −0.0059 (12) O2 0.0580 (17) 0.0460 (17) 0.0404 (15) −0.0186 (13) 0.0215 (13) −0.0060 (13) O3A 0.098 (13) 0.070 (13) 0.070 (11) −0.035 (8) 0.032 (8) −0.038 (8) O4A 0.082 (9) 0.066 (10) 0.063 (11) −0.017 (9) 0.047 (10) 0.002 (7)
O3B 0.13 (2) 0.056 (7) 0.039 (6) 0.010 (7) 0.036 (9) −0.009 (6)
O4B 0.103 (13) 0.036 (6) 0.060 (7) −0.007 (6) 0.021 (7) −0.006 (4)
O5 0.0428 (15) 0.0512 (19) 0.0678 (19) −0.0171 (13) 0.0181 (13) −0.0080 (15) N1 0.0445 (18) 0.0353 (19) 0.0341 (17) −0.0055 (14) 0.0111 (13) −0.0012 (14) N2 0.054 (2) 0.043 (2) 0.0395 (18) −0.0119 (16) 0.0202 (15) −0.0057 (16)
N3 0.061 (2) 0.060 (3) 0.046 (2) −0.013 (2) 0.0140 (18) −0.014 (2)
N4 0.0330 (16) 0.0357 (18) 0.0388 (17) −0.0032 (14) 0.0106 (14) 0.0023 (14) C1 0.0325 (19) 0.033 (2) 0.042 (2) −0.0027 (16) 0.0077 (15) −0.0021 (17) C2 0.0318 (19) 0.037 (2) 0.039 (2) −0.0009 (15) 0.0076 (15) 0.0003 (16) C3 0.036 (2) 0.042 (2) 0.052 (2) −0.0085 (18) 0.0128 (17) 0.003 (2) C4 0.043 (2) 0.037 (2) 0.056 (3) −0.0079 (17) 0.0035 (19) −0.0061 (19)
C5 0.053 (2) 0.050 (3) 0.040 (2) −0.006 (2) 0.0078 (18) −0.006 (2)
C6 0.051 (2) 0.047 (3) 0.039 (2) −0.0079 (19) 0.0086 (18) −0.0015 (18) C7 0.040 (2) 0.043 (2) 0.045 (2) −0.0061 (18) 0.0155 (17) 0.0052 (19) C8 0.039 (2) 0.043 (2) 0.037 (2) −0.0021 (17) 0.0078 (16) 0.0011 (17) C9 0.037 (2) 0.042 (2) 0.034 (2) −0.0031 (17) 0.0048 (15) 0.0015 (17) C10 0.057 (3) 0.036 (2) 0.045 (2) −0.0115 (19) 0.0161 (19) −0.0032 (18)
C11 0.054 (2) 0.047 (3) 0.040 (2) −0.008 (2) 0.0143 (18) 0.0018 (19)
C12 0.041 (2) 0.041 (2) 0.035 (2) −0.0018 (17) 0.0058 (16) −0.0049 (17)
C13 0.050 (2) 0.043 (2) 0.052 (2) −0.016 (2) 0.0132 (19) −0.007 (2)
C14 0.051 (2) 0.051 (3) 0.043 (2) −0.011 (2) 0.0158 (18) 0.001 (2)
C15 0.057 (2) 0.054 (3) 0.046 (2) −0.024 (2) 0.0192 (19) −0.019 (2)
C16 0.054 (3) 0.048 (3) 0.073 (3) −0.019 (2) 0.025 (2) −0.014 (2)
C17 0.050 (2) 0.062 (3) 0.050 (3) −0.015 (2) 0.023 (2) −0.003 (2)
supporting information
sup-4 Acta Cryst. (2005). E61, m1310–m1312
Geometric parameters (Å, º)
Cu1—O1 1.886 (2) C4—H4A 0.9300
Cu1—O2 1.923 (3) C5—C6 1.370 (5)
Cu1—N1 1.924 (3) C5—H5A 0.9300
Cu1—N4 2.019 (3) C6—H6A 0.9300
O1—C1 1.312 (4) C7—H7A 0.9300
O2—C8 1.296 (4) C8—C9 1.487 (5)
O3A—N3 1.17 (2) C9—C14 1.382 (5)
O4A—N3 1.19 (2) C9—C10 1.396 (5)
O3B—N3 1.24 (3) C10—C11 1.371 (5)
O4B—N3 1.30 (2) C10—H10A 0.9300
O5—C17 1.414 (5) C11—C12 1.380 (5)
O5—C16 1.414 (5) C11—H11A 0.9300
N1—C7 1.279 (5) C12—C13 1.370 (5)
N1—N2 1.406 (4) C13—C14 1.365 (5)
N2—C8 1.294 (5) C13—H13A 0.9300
N3—C12 1.456 (5) C14—H14A 0.9300
N4—C15 1.470 (5) C15—C16 1.496 (5)
N4—C18 1.477 (4) C15—H15A 0.9700
N4—H4N 0.9100 C15—H15B 0.9700
C1—C6 1.400 (5) C16—H16A 0.9700
C1—C2 1.424 (5) C16—H16B 0.9700
C2—C3 1.393 (5) C17—C18 1.512 (5)
C2—C7 1.427 (5) C17—H17A 0.9700
C3—C4 1.366 (5) C17—H17B 0.9700
C3—H3A 0.9300 C18—H18A 0.9700
C4—C5 1.385 (5) C18—H18B 0.9700
O1—Cu1—O2 173.66 (10) C2—C7—H7A 117.7
O1—Cu1—N1 93.38 (12) N2—C8—O2 125.4 (4)
O2—Cu1—N1 81.24 (12) N2—C8—C9 118.4 (3)
O1—Cu1—N4 92.24 (11) O2—C8—C9 116.1 (3)
O2—Cu1—N4 93.30 (11) C14—C9—C10 118.5 (4)
N1—Cu1—N4 173.77 (12) C14—C9—C8 120.1 (3)
C1—O1—Cu1 127.1 (2) C10—C9—C8 121.4 (4)
C8—O2—Cu1 110.3 (2) C11—C10—C9 120.9 (4)
O4B—O3A—N3 88 (5) C11—C10—H10A 119.5
O3A—O4B—N3 64 (4) C9—C10—H10A 119.5
C17—O5—C16 110.1 (3) C10—C11—C12 118.4 (4)
C7—N1—N2 117.8 (3) C10—C11—H11A 120.8
C7—N1—Cu1 127.4 (3) C12—C11—H11A 120.8
N2—N1—Cu1 114.6 (2) C13—C12—C11 121.8 (4)
C8—N2—N1 108.4 (3) C13—C12—N3 118.7 (4)
O3A—N3—O4A 122.9 (17) C11—C12—N3 119.5 (3)
O3B—N3—O4B 124.3 (16) C14—C13—C12 119.1 (4)
O3A—N3—C12 117.6 (11) C14—C13—H13A 120.5
supporting information
sup-5 Acta Cryst. (2005). E61, m1310–m1312
O3B—N3—C12 118.7 (12) C13—C14—C9 121.1 (4)
O4B—N3—C12 116.8 (11) C13—C14—H14A 119.4
C15—N4—C18 108.9 (3) C9—C14—H14A 119.4
C15—N4—Cu1 116.0 (2) N4—C15—C16 112.6 (3)
C18—N4—Cu1 114.5 (2) N4—C15—H15A 109.1
C15—N4—H4N 105.5 C16—C15—H15A 109.1
C18—N4—H4N 105.5 N4—C15—H15B 109.1
Cu1—N4—H4N 105.5 C16—C15—H15B 109.1
O1—C1—C6 118.6 (3) H15A—C15—H15B 107.8
O1—C1—C2 124.7 (3) O5—C16—C15 112.1 (4)
C6—C1—C2 116.7 (3) O5—C16—H16A 109.2
C3—C2—C1 119.2 (3) C15—C16—H16A 109.2
C3—C2—C7 118.2 (3) O5—C16—H16B 109.2
C1—C2—C7 122.6 (3) C15—C16—H16B 109.2
C4—C3—C2 122.8 (3) H16A—C16—H16B 107.9
C4—C3—H3A 118.6 O5—C17—C18 111.6 (3)
C2—C3—H3A 118.6 O5—C17—H17A 109.3
C3—C4—C5 118.2 (4) C18—C17—H17A 109.3
C3—C4—H4A 120.9 O5—C17—H17B 109.3
C5—C4—H4A 120.9 C18—C17—H17B 109.3
C6—C5—C4 120.8 (4) H17A—C17—H17B 108.0
C6—C5—H5A 119.6 N4—C18—C17 111.3 (3)
C4—C5—H5A 119.6 N4—C18—H18A 109.4
C5—C6—C1 122.3 (4) C17—C18—H18A 109.4
C5—C6—H6A 118.8 N4—C18—H18B 109.4
C1—C6—H6A 118.8 C17—C18—H18B 109.4
N1—C7—C2 124.7 (3) H18A—C18—H18B 108.0
N1—C7—H7A 117.7
N1—Cu1—O1—C1 2.9 (3) C1—C2—C7—N1 −1.9 (6)
N4—Cu1—O1—C1 −179.8 (3) N1—N2—C8—O2 −0.2 (5)
N1—Cu1—O2—C8 −1.5 (3) N1—N2—C8—C9 177.0 (3)
N4—Cu1—O2—C8 −178.5 (3) Cu1—O2—C8—N2 1.5 (5)
O1—Cu1—N1—C7 −0.4 (3) Cu1—O2—C8—C9 −175.9 (2)
O2—Cu1—N1—C7 176.2 (3) N2—C8—C9—C14 −173.0 (4)
O1—Cu1—N1—N2 −175.1 (2) O2—C8—C9—C14 4.6 (5)
O2—Cu1—N1—N2 1.5 (2) N2—C8—C9—C10 7.2 (6)
C7—N1—N2—C8 −176.4 (3) O2—C8—C9—C10 −175.3 (3)
Cu1—N1—N2—C8 −1.1 (4) C14—C9—C10—C11 −0.2 (6)
O4B—O3A—N3—O4A −91 (5) C8—C9—C10—C11 179.7 (4)
O4B—O3A—N3—O3B −111 (5) C9—C10—C11—C12 0.2 (6)
O4B—O3A—N3—C12 96 (4) C10—C11—C12—C13 1.0 (6)
O3A—O4B—N3—O4A 106 (5) C10—C11—C12—N3 −179.7 (4)
O3A—O4B—N3—O3B 86 (5) O3A—N3—C12—C13 −16.9 (10)
O3A—O4B—N3—C12 −99 (4) O4A—N3—C12—C13 169 (2)
O1—Cu1—N4—C15 −162.5 (3) O3B—N3—C12—C13 −170 (2)
O2—Cu1—N4—C15 20.6 (3) O4B—N3—C12—C13 14.6 (10)
supporting information
sup-6 Acta Cryst. (2005). E61, m1310–m1312
O2—Cu1—N4—C18 148.9 (3) O4A—N3—C12—C11 −10 (2)
Cu1—O1—C1—C6 175.7 (3) O3B—N3—C12—C11 10 (2)
Cu1—O1—C1—C2 −5.2 (5) O4B—N3—C12—C11 −164.7 (9)
O1—C1—C2—C3 −178.5 (3) C11—C12—C13—C14 −2.2 (6)
C6—C1—C2—C3 0.5 (5) N3—C12—C13—C14 178.5 (4)
O1—C1—C2—C7 4.6 (6) C12—C13—C14—C9 2.2 (6)
C6—C1—C2—C7 −176.4 (3) C10—C9—C14—C13 −1.0 (6)
C1—C2—C3—C4 −0.6 (6) C8—C9—C14—C13 179.1 (4)
C7—C2—C3—C4 176.5 (4) C18—N4—C15—C16 51.9 (5)
C2—C3—C4—C5 −0.4 (6) Cu1—N4—C15—C16 −177.2 (3)
C3—C4—C5—C6 1.5 (6) C17—O5—C16—C15 57.9 (5)
C4—C5—C6—C1 −1.6 (6) N4—C15—C16—O5 −55.7 (5)
O1—C1—C6—C5 179.6 (4) C16—O5—C17—C18 −58.9 (5)
C2—C1—C6—C5 0.5 (6) C15—N4—C18—C17 −52.4 (4)
N2—N1—C7—C2 174.7 (3) Cu1—N4—C18—C17 175.9 (3)
Cu1—N1—C7—C2 0.2 (6) O5—C17—C18—N4 57.4 (5)
