metal-organic papers
m916
Liet al. [Cu(C10H8N2)(C4H2O4)(H2O)].2H2O doi:10.1107/S1600536806011020 Acta Cryst.(2006). E62, m916–m918
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
Aqua(2,2
000-bipyridine)maleatocopper(II)
dihydrate
Ming-Tian Li,a,bXu-Cheng Fuc and Cheng-Gang Wanga*
a
Department of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People’s Republic of China,bDepartment of Chemistry, Shangqiu Normal University, Shangqiu, Henan 476000, People’s Republic of China, andcChemistry and Biology Department, West Anhui University, Liu an Anhui 237000, People’s Republic of China
Correspondence e-mail: wangcg23@yahoo.com.cn
Key indicators
Single-crystal X-ray study
T= 292 K
Mean(C–C) = 0.006 A˚
Rfactor = 0.052
wRfactor = 0.123
Data-to-parameter ratio = 14.6
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 17 March 2006 Accepted 27 March 2006
#2006 International Union of Crystallography
All rights reserved
In the molecule of the title compound, [Cu(C10H8N2)-(C4H2O4)(H2O)]2H2O, the Cu(II) atom has elongated tetra-gonal pyramidal geometry, coordinated by one water O atom, two N atoms of the 2,20-bipyridine ligand and two O atoms of
the two carboxylate groups of the maleate dianion. The molecules are linked through hydrogen-bonding and –
stacking interactions, forming a two-dimensional supra-molecular structure.
Comment
Metal–organic coordination complexes containing the maleate ligand have been studied extensively due to their wide range of applications (Maruoka et al., 1993; Chen & Suslick, 1993; Hoskins & Robson, 1990; Kondoet al., 1997). Here, we report the crystal structure of one such complex, the title compound, (I).
The structure of (I) consists of discrete monomers. The CuII atom exhibits an elongated tetragonal pyramidal geometry, coordinated by one water O atom, two N atoms of the 2,20
-bipyridine ligand and two O atoms of the two carboxylate groups of the maleate dianion (Table 1, Fig. 1).
The Cu—O(maleate) and Cu—O(water) bonds (Table 1) are slightly longer than the corresponding ones [1.876 (6), 1.894 (6) and 2.150 (6) A˚ ] in [Cu(pz)2(male)(H2O)] -1.5H2O, (II), where pz and male are 3,5-dimethylpyrazole and the maleate anion, respectively (Chen et al., 2003). It is not possible to compare the Cu—O(water) bond in (I) with those [1.975 (2) and 2.414 (2) A˚ ] reported in {[Cu(4,40
In the crystal structure, the molecules are packed via hydrogen bonds (Fig. 2) between water molecules and the uncoordinated O(maleate) atoms of neighbouring molecules (Table 2), and – stacking interactions with centroid– centroid distances of 3.811 (3) and 3.974 (3) A˚ between the pyridine ring of the molecule at (x;y;z) and those at (2x, y, 2z) and (2x,y, 1z), respectively, forming a two-dimensional supramolecular structure.
Experimental
Cu(NO3)23H2O (0.241 g, 1.0 mmol) was added slowly to an aqueous solution of maleic acid (0.116 g, 1.0 mmol, 15 ml), and the reaction mixture was stirred for 1 h at 353 K. An ethanol solution (5 ml) of 2,20-bipyridine (0.156 g, 1.0 mmol) was then added with continuous
stirring. NaOH solution (0.1 mol/l) was added until a pH of 7 was obtained. After 1 h, the reaction mixture was cooled to room temperature and then filtered. Blue single crystals were obtained from the filtrate after two weeks (yield 139.9 mg, 36%, m.p. 525 K).
Crystal data
[Cu(C10H8N2)(C4H2O4
)-(H2O)]2H2O
Mr= 387.83
Monoclinic,P21=c
a= 8.9793 (18) A˚
b= 22.487 (5) A˚
c= 7.7187 (15) A˚
= 95.62 (3) V= 1551.0 (5) A˚3
Z= 4
Dx= 1.661 Mg m 3
MoKradiation Cell parameters from 3123
reflections
= 2.6–27.8
= 1.45 mm1
T= 292 (2) K Block, blue
0.200.060.06 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin= 0.760,Tmax= 0.918
10456 measured reflections
3528 independent reflections 2257 reflections withI> 2(I)
Rint= 0.073
max= 27.5
h=11!11
k=28!24
l=9!6
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.052
wR(F2) = 0.123
S= 0.97 3528 reflections 241 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2(F
o2) + (0.05P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.42 e A˚
3
min=0.36 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
Cu1—O1 1.931 (3) Cu1—O3 1.931 (3) Cu1—O5 2.261 (3)
Cu1—N1 2.003 (3) Cu1—N2 2.003 (3) O1—Cu1—O3 93.44 (12)
O3—Cu1—N1 91.72 (12) O1—Cu1—N2 90.55 (12) N1—Cu1—N2 80.53 (13)
[image:2.610.52.292.68.311.2]O1—Cu1—O5 107.62 (12) O3—Cu1—O5 100.11 (12) N1—Cu1—O5 86.57 (12) N2—Cu1—O5 93.38 (12)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O5—H5a O7i
0.80 (3) 1.96 (3) 2.752 (5) 172 (5) O7—H7b O6 0.75 (3) 2.07 (4) 2.819 (6) 174 (5) O6—H6a O4ii 0.75 (4) 2.18 (4) 2.889 (5) 159 (7) O7—H7a O2 0.83 (4) 2.03 (4) 2.850 (5) 169 (5) O5—H5b O4iii
0.80 (3) 1.99 (3) 2.783 (4) 174 (4) O6—H6b O2iv
0.79 (4) 2.14 (4) 2.903 (5) 162 (6)
Symmetry codes: (i) x;y;zþ1; (ii) xþ1;yþ3 2;z
1
2; (iii) x;yþ 3 2;zþ
1 2; (iv)
x;yþ3 2;z
1 2.
Atoms H5a, H5b, H6a, H6b, H7a and H7b were located in a difference map and refined isotropically [O—H = 0.75 (3)–0.83 (4) A˚ andUiso(H) = 0.043 (17)–0.10 (3) A˚
2]. The remaining H atoms were
positioned geometrically, with C—H = 0.93 A˚ for aromatic H, and constrained to ride on their parent atoms, withUiso(H) = 1.2Ueq(C). Data collection:SMART(Bruker, 2000); cell refinement:SAINT
(Bruker, 2000); data reduction:SAINT; program(s) used to solve
metal-organic papers
Acta Cryst.(2006). E62, m916–m918 Liet al. [Cu(C
10H8N2)(C4H2O4)(H2O)].2H2O
m917
Figure 1 [image:2.610.315.563.73.188.2]The asymmetric unit, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. Hydrogen bonds are shown as dashed lines.
Figure 2
[image:2.610.313.566.568.641.2]structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.
This work was supported by the Hubei Key Laboratory of Novel Chemical Reactors and Green Chemical Technology (grant No. RCT2004011).
References
Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2000).SMART(Version 6.10),SAINT(Version 6.10) andSADABS
(Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Chen, C.-T. & Suslick, K. S. (1993).Coord. Chem. Rev.128, 293–322. Chen, X.-Y., Shen, W.-Z., Cheng, P., Yan, S.-P., Liao, D.-Z. & Jiang, Z.-H.
(2003).Z. Anorg. Allg. Chem.629, 697–702.
Hoskins, B. F. & Robson, R. (1990). J. Am. Chem. Soc. 112, 1546– 1554.
Kang, Y., Li, -Z. J., Qin, Y.-Y., Chen, Y.-B., Zhang, J., Hu, R.-F., Wen, Y.-H., Cheng, J.-K. & Yao, Y.-G. (2004).Chin. J. Struct. Chem.23, 862–864. Kondo, M., Yoshitomi, T., Seki, K., Matsuzaka, H. & Kitagawa, S. (1997).
Angew. Chem. Int. Ed. Engl.36, 1725–1727.
Maruoka, K., Murase, N. & Yamamoto, H. (1993).J. Org. Chem.58, 2938– 2939.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
metal-organic papers
m918
Liet al. [Cu(Csupporting information
sup-1
Acta Cryst. (2006). E62, m916–m918
supporting information
Acta Cryst. (2006). E62, m916–m918 [https://doi.org/10.1107/S1600536806011020]
Aqua(2,2
′
-bipyridine)maleatocopper(II) dihydrate
Ming-Tian Li, Xu-Cheng Fu and Cheng-Gang Wang
Aquamaleato(2,2′-bipyridine)copper(II) dihydrate
Crystal data
[Cu(C10H8N2)(C4H2O4)(H2O)].2H2O
Mr = 387.83
Monoclinic, P21/c Hall symbol: -P 2ybc
a = 8.9793 (18) Å
b = 22.487 (5) Å
c = 7.7187 (15) Å
β = 95.62 (3)°
V = 1551.0 (5) Å3
Z = 4
F(000) = 796
Dx = 1.661 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3123 reflections
θ = 2.6–27.8°
µ = 1.45 mm−1
T = 292 K
Block, blue
0.20 × 0.06 × 0.06 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; Bruker, 2000) Tmin = 0.760, Tmax = 0.918
10456 measured reflections 3528 independent reflections 2257 reflections with I > 2σ(I) Rint = 0.073
θmax = 27.5°, θmin = 1.8°
h = −11→11
k = −28→24
l = −9→6
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.052
wR(F2) = 0.123
S = 0.97
3528 reflections 241 parameters 6 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) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001
Δρmax = 0.42 e Å−3 Δρmin = −0.36 e Å−3
Special details
supporting information
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Acta Cryst. (2006). E62, m916–m918
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
Cu1 0.08386 (5) 0.60739 (2) 0.63719 (6) 0.02924 (17)
O1 0.2542 (3) 0.62204 (12) 0.5087 (4) 0.0431 (8)
O2 0.4522 (3) 0.67026 (13) 0.4346 (4) 0.0435 (8)
O3 −0.0163 (3) 0.67980 (12) 0.5575 (4) 0.0407 (7)
O4 −0.0346 (3) 0.77636 (13) 0.5061 (4) 0.0455 (8)
O5 0.1509 (4) 0.63151 (14) 0.9184 (4) 0.0354 (7)
H5a 0.235 (4) 0.637 (2) 0.959 (6) 0.050 (15)*
H5b 0.102 (4) 0.6584 (18) 0.950 (5) 0.043 (15)*
O6 0.6422 (5) 0.7250 (2) −0.0366 (6) 0.0673 (12)
H6a 0.723 (5) 0.725 (3) 0.000 (8) 0.10 (3)*
H6b 0.606 (6) 0.7568 (19) −0.054 (7) 0.08 (2)*
O7 0.4389 (4) 0.64095 (17) 0.0742 (6) 0.0473 (9)
H7a 0.451 (5) 0.646 (2) 0.181 (5) 0.053 (17)*
H7b 0.497 (5) 0.661 (2) 0.043 (6) 0.043 (17)*
N1 −0.1045 (3) 0.57454 (15) 0.7188 (4) 0.0312 (8)
N2 0.1452 (3) 0.52221 (14) 0.6714 (4) 0.0269 (7)
C1 −0.2298 (4) 0.6060 (2) 0.7369 (6) 0.0407 (11)
H1 −0.2329 0.6462 0.7085 0.049*
C2 −0.3532 (4) 0.5797 (2) 0.7966 (6) 0.0500 (13)
H2 −0.4393 0.6018 0.8071 0.060*
C3 −0.3484 (5) 0.5206 (2) 0.8406 (6) 0.0508 (13)
H3 −0.4307 0.5023 0.8823 0.061*
C4 −0.2196 (5) 0.4885 (2) 0.8223 (5) 0.0429 (11)
H4 −0.2147 0.4483 0.8502 0.051*
C5 −0.0990 (4) 0.51663 (18) 0.7623 (5) 0.0302 (9)
C6 0.0423 (4) 0.48682 (18) 0.7357 (5) 0.0297 (9)
C7 0.0717 (5) 0.42719 (19) 0.7704 (5) 0.0407 (11)
H7 0.0005 0.4033 0.8157 0.049*
C8 0.2087 (5) 0.4037 (2) 0.7368 (6) 0.0480 (12)
H8 0.2302 0.3638 0.7587 0.058*
C9 0.3121 (5) 0.4400 (2) 0.6708 (6) 0.0453 (12)
H9 0.4049 0.4252 0.6478 0.054*
C10 0.2763 (4) 0.49848 (19) 0.6394 (5) 0.0375 (10)
H10 0.3465 0.5228 0.5936 0.045*
C11 0.3419 (4) 0.66653 (18) 0.5198 (5) 0.0312 (9)
C12 0.3159 (4) 0.71698 (17) 0.6396 (5) 0.0304 (9)
H12 0.3995 0.7306 0.7091 0.037*
C13 0.1889 (4) 0.74438 (17) 0.6585 (5) 0.0294 (9)
H13 0.1941 0.7752 0.7391 0.035*
supporting information
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Acta Cryst. (2006). E62, m916–m918
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Cu1 0.0301 (3) 0.0223 (3) 0.0358 (3) −0.0035 (2) 0.0056 (2) 0.0006 (2)
O1 0.0499 (18) 0.0297 (18) 0.053 (2) −0.0103 (13) 0.0236 (15) −0.0069 (14)
O2 0.0315 (15) 0.046 (2) 0.056 (2) −0.0033 (13) 0.0152 (14) 0.0012 (15)
O3 0.0393 (16) 0.0251 (17) 0.055 (2) −0.0079 (13) −0.0075 (14) 0.0061 (14)
O4 0.0351 (15) 0.0292 (17) 0.071 (2) 0.0022 (13) 0.0015 (15) 0.0161 (15)
O5 0.0380 (18) 0.0312 (18) 0.0367 (18) −0.0018 (15) 0.0017 (15) −0.0043 (14)
O6 0.041 (2) 0.052 (3) 0.109 (4) 0.003 (2) 0.009 (2) 0.000 (2)
O7 0.0375 (19) 0.053 (2) 0.051 (3) 0.0041 (17) 0.0032 (18) −0.0050 (19)
N1 0.0278 (17) 0.032 (2) 0.034 (2) −0.0037 (14) 0.0026 (15) −0.0038 (15)
N2 0.0302 (16) 0.0234 (18) 0.0272 (18) −0.0019 (14) 0.0027 (14) −0.0003 (14)
C1 0.035 (2) 0.044 (3) 0.043 (3) 0.004 (2) 0.007 (2) −0.009 (2)
C2 0.025 (2) 0.076 (4) 0.050 (3) 0.004 (2) 0.011 (2) −0.012 (3)
C3 0.039 (3) 0.077 (4) 0.040 (3) −0.016 (3) 0.016 (2) 0.003 (3)
C4 0.045 (3) 0.046 (3) 0.039 (3) −0.015 (2) 0.008 (2) 0.003 (2)
C5 0.037 (2) 0.029 (2) 0.025 (2) −0.0082 (18) 0.0021 (17) −0.0002 (17)
C6 0.034 (2) 0.027 (2) 0.026 (2) −0.0042 (17) −0.0029 (17) −0.0023 (17)
C7 0.052 (3) 0.028 (3) 0.041 (3) −0.006 (2) −0.003 (2) 0.0048 (19)
C8 0.059 (3) 0.033 (3) 0.049 (3) 0.013 (2) −0.010 (2) 0.000 (2)
C9 0.039 (2) 0.045 (3) 0.051 (3) 0.016 (2) −0.002 (2) −0.002 (2)
C10 0.035 (2) 0.040 (3) 0.037 (2) 0.0006 (19) 0.0006 (19) −0.003 (2)
C11 0.029 (2) 0.030 (2) 0.034 (2) −0.0015 (17) −0.0018 (18) 0.0075 (18)
C12 0.035 (2) 0.029 (2) 0.026 (2) −0.0064 (17) −0.0003 (18) 0.0055 (17)
C13 0.036 (2) 0.024 (2) 0.028 (2) −0.0058 (17) 0.0023 (18) −0.0007 (17)
C14 0.032 (2) 0.031 (2) 0.033 (2) 0.0005 (18) 0.0083 (18) 0.0004 (19)
Geometric parameters (Å, º)
Cu1—O1 1.931 (3) C10—C9 1.369 (6)
Cu1—O3 1.931 (3) C10—H10 0.9300
Cu1—O5 2.261 (3) C11—C12 1.497 (6)
Cu1—N1 2.003 (3) C12—C13 1.317 (5)
Cu1—N2 2.003 (3) C12—H12 0.9300
O3—C14 1.270 (4) C7—C8 1.386 (6)
O5—H5a 0.80 (3) C7—H7 0.9300
O5—H5b 0.80 (3) C9—C8 1.372 (6)
O1—C11 1.271 (4) C9—H9 0.9300
N2—C10 1.338 (5) C8—H8 0.9300
N2—C6 1.350 (5) C13—H13 0.9300
O4—C14 1.244 (5) C4—C3 1.382 (6)
O2—C11 1.244 (4) C4—H4 0.9300
N1—C5 1.345 (5) C2—C3 1.371 (7)
N1—C1 1.348 (5) C2—H2 0.9300
C6—C7 1.388 (5) C3—H3 0.9300
C6—C5 1.467 (5) O7—H7b 0.75 (3)
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Acta Cryst. (2006). E62, m916–m918
C14—C13 1.505 (5) O6—H6a 0.75 (4)
C1—C2 1.374 (6) O6—H6b 0.79 (4)
C1—H1 0.9300
O1—Cu1—O3 93.44 (12) N2—C10—C9 123.1 (4)
O1—Cu1—N1 163.76 (13) N2—C10—H10 118.5
O3—Cu1—N1 91.72 (12) C9—C10—H10 118.5
O1—Cu1—N2 90.55 (12) O2—C11—O1 122.5 (4)
O3—Cu1—N2 164.04 (12) O2—C11—C12 117.1 (4)
N1—Cu1—N2 80.53 (13) O1—C11—C12 120.4 (4)
O1—Cu1—O5 107.62 (12) C13—C12—C11 127.7 (4)
O3—Cu1—O5 100.11 (12) C13—C12—H12 116.1
N1—Cu1—O5 86.57 (12) C11—C12—H12 116.1
N2—Cu1—O5 93.38 (12) C8—C7—C6 119.2 (4)
C14—O3—Cu1 127.3 (3) C8—C7—H7 120.4
Cu1—O5—H5a 125 (3) C6—C7—H7 120.4
Cu1—O5—H5b 112 (3) C10—C9—C8 118.8 (4)
H5a—O5—H5b 106 (4) C10—C9—H9 120.6
C11—O1—Cu1 128.1 (3) C8—C9—H9 120.6
C10—N2—C6 118.6 (4) C9—C8—C7 119.2 (4)
C10—N2—Cu1 126.3 (3) C9—C8—H8 120.4
C6—N2—Cu1 115.0 (3) C7—C8—H8 120.4
C5—N1—C1 119.5 (4) C12—C13—C14 128.4 (4)
C5—N1—Cu1 115.1 (3) C12—C13—H13 115.8
C1—N1—Cu1 125.4 (3) C14—C13—H13 115.8
N2—C6—C7 121.1 (4) C5—C4—C3 119.3 (4)
N2—C6—C5 114.5 (3) C5—C4—H4 120.3
C7—C6—C5 124.4 (4) C3—C4—H4 120.3
N1—C5—C4 121.3 (4) C3—C2—C1 119.6 (4)
N1—C5—C6 114.7 (3) C3—C2—H2 120.2
C4—C5—C6 123.9 (4) C1—C2—H2 120.2
O4—C14—O3 123.1 (4) C2—C3—C4 119.1 (4)
O4—C14—C13 116.2 (4) C2—C3—H3 120.5
O3—C14—C13 120.7 (3) C4—C3—H3 120.5
N1—C1—C2 121.2 (4) H7b—O7—H7a 102 (5)
N1—C1—H1 119.4 H6a—O6—H6b 116 (6)
C2—C1—H1 119.4
O1—Cu1—O3—C14 −53.2 (3) C1—N1—C5—C6 179.5 (3)
N1—Cu1—O3—C14 142.2 (3) Cu1—N1—C5—C6 −2.4 (4)
N2—Cu1—O3—C14 −157.4 (4) N2—C6—C5—N1 0.0 (5)
O5—Cu1—O3—C14 55.4 (3) C7—C6—C5—N1 −179.4 (4)
O3—Cu1—O1—C11 58.3 (3) N2—C6—C5—C4 178.3 (4)
N1—Cu1—O1—C11 166.6 (4) C7—C6—C5—C4 −1.1 (6)
N2—Cu1—O1—C11 −137.2 (3) Cu1—O3—C14—O4 177.4 (3)
O5—Cu1—O1—C11 −43.4 (4) Cu1—O3—C14—C13 −4.7 (5)
O1—Cu1—N2—C10 11.8 (3) C5—N1—C1—C2 −1.0 (6)
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N1—Cu1—N2—C10 178.2 (3) C6—N2—C10—C9 −0.9 (6)
O5—Cu1—N2—C10 −95.9 (3) Cu1—N2—C10—C9 178.0 (3)
O1—Cu1—N2—C6 −169.2 (3) Cu1—O1—C11—O2 177.2 (3)
O3—Cu1—N2—C6 −64.7 (5) Cu1—O1—C11—C12 −2.2 (5)
N1—Cu1—N2—C6 −2.9 (2) O2—C11—C12—C13 134.2 (4)
O5—Cu1—N2—C6 83.1 (3) O1—C11—C12—C13 −46.3 (6)
O1—Cu1—N1—C5 60.3 (6) N2—C6—C7—C8 −0.6 (6)
O3—Cu1—N1—C5 168.8 (3) C5—C6—C7—C8 178.7 (4)
N2—Cu1—N1—C5 2.9 (3) N2—C10—C9—C8 0.6 (6)
O5—Cu1—N1—C5 −91.1 (3) C10—C9—C8—C7 −0.3 (7)
O1—Cu1—N1—C1 −121.7 (5) C6—C7—C8—C9 0.3 (6)
O3—Cu1—N1—C1 −13.1 (3) C11—C12—C13—C14 0.5 (7)
N2—Cu1—N1—C1 −179.1 (3) O4—C14—C13—C12 −132.4 (4)
O5—Cu1—N1—C1 86.9 (3) O3—C14—C13—C12 49.6 (6)
C10—N2—C6—C7 0.8 (5) N1—C5—C4—C3 −1.0 (6)
Cu1—N2—C6—C7 −178.2 (3) C6—C5—C4—C3 −179.2 (4)
C10—N2—C6—C5 −178.6 (3) N1—C1—C2—C3 0.8 (7)
Cu1—N2—C6—C5 2.4 (4) C1—C2—C3—C4 −0.6 (7)
C1—N1—C5—C4 1.1 (6) C5—C4—C3—C2 0.7 (7)
Cu1—N1—C5—C4 179.3 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O5—H5a···O7i 0.80 (3) 1.96 (3) 2.752 (5) 172 (5)
O7—H7b···O6 0.75 (3) 2.07 (4) 2.819 (6) 174 (5)
O6—H6a···O4ii 0.75 (4) 2.18 (4) 2.889 (5) 159 (7)
O7—H7a···O2 0.83 (4) 2.03 (4) 2.850 (5) 169 (5)
O5—H5b···O4iii 0.80 (3) 1.99 (3) 2.783 (4) 174 (4)
O6—H6b···O2iv 0.79 (4) 2.14 (4) 2.903 (5) 162 (6)
