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ISSN: 2056-9890

Crystal structure and Hirshfeld surface analysis of a copper(II) complex with ethyl­enedi­amine and non-coordinated benzoate

aDepartment of Chemistry, College of Science, Salahaddin University, Erbil, Iraq, bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Kurupelit, Samsun, Turkey, cInstitute of Chemical Sciences, School of Engineering & Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK, and dDepartment of Chemistry, Taras Shevchenko National University of Kyiv, 64, Vladimirska Str., Kiev 01601, Ukraine
*Correspondence e-mail: sevgi.kansiz85@gmail.com, tiskenderov@ukr.net

Edited by A. J. Lough, University of Toronto, Canada (Received 15 November 2019; accepted 11 December 2019; online 1 January 2020)

In the title compound, di­aqua­bis­(ethyl­enedi­amine-κ2N,N′)copper(II) bis­(2-nitro­benzoate), [Cu(C2H8N2)2(H2O)2](C7H4NO4)2, two di­aqua­bis­(ethyl­enedi­amine)­copper(II) cations and four nitro­benzoate anions are present in the asymmetric unit. All four anions are `whole-mol­ecule' disordered over two sets of sites. The major components have refined occupancies of 0.572 (13), 0.591 (9), 0.601 (9) and 0.794 (10). The CuII ions exhibit slightly distorted octa­hedral geometries. In the crystal, cations and anions are connected to each other via N—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (200). The inter­molecular contacts in the crystal were further analysed using Hirshfeld surface analysis, which indicates that the most significant contacts are O⋯H/H⋯O (42.9%), followed by H⋯H (35.7%), C⋯H/H⋯C (14.2%), C⋯C (2.9%), C⋯O/O⋯C (2.2%), N⋯H/H⋯N (0.9%) and N⋯O/O⋯N (0.3%).

1. Chemical context

Carboxyl­ates are employed in the synthesis of new transition-metal complexes because they can stabilize them and additionally display different coordination modes such as monodendate, bidendate, bridging (synsyn, synanti or antianti mode) and ionic. Copper(II) carboxyl­ates have been used as single precursors for the preparation of copper(II) oxide nanoparticles (Karthik & Qadir, 2019[Karthik, K. & Qadir, A. M. (2019). J. Struct. Chem. 60, 1172-1178.]). Copper(II) complexes containing ethyl­enedi­amine derivatives and carboxyl­ate have shown anti­bacterial activity against pathogenic bacteria (Kumar et al., 2013[Kumar, R., Obrai, S., Kaur, A., Hundal, G., Meehnian, H. & Jana, A. K. (2013). Polyhedron, 56, 55-61.]). It has been reported that some copper(II) carboxyl­ate complexes involving nitro­gen donor ligands exhibit carbonic anhydrase inhibitory activity (Dilek et al., 2017[Dilek, E., Caglar, S., Dogancay, N., Caglar, B., Sahin, O. & Tabak, A. (2017). J. Coord. Chem. 70, 2833-2852.]). Ethyl­enedi­amine has good coordination and chelating ability, forming five-membered ring compounds with metal centers. Generally, these metallacycles display a twist conformation. Copper can take part in different biological processes. Thus, copper shows an important role in electron transfer, oxidation, and di­oxy­gen transport (Mirica et al., 2004[Mirica, L. M., Ottenwaelder, X. & Stack, T. D. P. (2004). Chem. Rev. 104, 1013-1046.]; Rosenzweig et al., 2006[Rosenzweig, A. C. & Sazinsky, M. H. (2006). Curr. Opin. Struct. Biol. 16, 729-735.]). In this paper, we report the synthesis, single crystal structure determination and Hirshfeld surface analysis of a copper(II) complex containing ethyl­enedi­amine and 2-nitro­benzoate.

[Scheme 1]

2. Structural commentary

The asymmetric unit of title compound is shown in Fig. 1[link] and selected geometric parameters are given in Table 1[link]. There are two independent bis­(ethyl­enedi­amine-κ2N)di­aqua­copper(II) cations and four 2-nitro­benzoate anions. In both cations, the CuII ion is coordinated by four N atoms of the ethyl­enedi­amine ligands which chelate the metal in the equatorial plane, and two axially coordinated water mol­ecules forming a slightly distorted octa­hedral geometry. The Cu—N bond lengths range from 1.991 (6) and 2.050 (5) Å (Table 1[link]) and are similar to those observed in the structures containing [Cu(en)2(H2O)2]2+ cations (Kovbasyuk et al., 1997[Kovbasyuk, L. A., Fritsky, I. O., Kokozay, V. N. & Iskenderov, T. S. (1997). Polyhedron, 16, 1723-1729.]; Gumienna-Kontecka et al., 2007[Gumienna-Kontecka, E., Golenya, I. A., Dudarenko, N. M., Dobosz, A., Haukka, M., Fritsky, I. O. & Świątek-Kozłowska, J. (2007). New J. Chem. 31, 1798-1805.]; Şen et al., 2017[Şen, F., Kansiz, S. & Uçar, İ. (2017). Acta Cryst. C73, 517-524.]). The axial Cu—O contacts in both conformers [2.599 (5) and 2.621 (5) Å for Cu1A and 2.557 (5) and 2.564 (5) Å for Cu1B] are noticeably longer than the equatorial Cu—N distances (Table 1[link]) as a consequence of the Jahn–Teller effect (Kovbasyuk et al., 1997[Kovbasyuk, L. A., Fritsky, I. O., Kokozay, V. N. & Iskenderov, T. S. (1997). Polyhedron, 16, 1723-1729.]). It is notable that although the complex cations are crystallographically non-centrosymmetric, the Cu—O bond lengths are very similar. In addition, the distances involving Cu1A and O are somewhat longer than for Cu1B. The N—O bond lengths [ranging from 1.223 (11) to 1.251 (15) Å] in the nitro group are close to the values observed for related compounds reported in the literature (Boulhaoua et al., 2019[Boulhaoua, M., Kansiz, S., El Hafi, M., Lahmidi, S., Dege, N., Benchidmi, M. & Mague, J. T. (2019). Acta Cryst. E75, 71-74.]; Kansız et al., 2018[Kansız, S., Çakmak, Ş., Dege, N., Meral, G. & Kütük, H. (2018). X-Ray Struct. Anal. Online, 34, 17-18.], 2019[Kansız, S., Dege, N., Aydin, A. S., Ağar, E. & Matushko, I. P. (2019). Acta Cryst. E75, 812-815.]).

Table 1
Selected geometric parameters (Å, °)

N1A—Cu1A 1.991 (6) N1B—Cu1B 1.999 (6)
Cu1A—N2A 2.044 (5) Cu1B—N2B 2.050 (5)
Cu1A—N3A 2.012 (6) Cu1B—N3B 2.004 (6)
Cu1A—N4A 2.017 (5) Cu1B—N4B 2.031 (5)
Cu1A—O1W 2.621 (5) Cu1B—O2W 2.557 (5)
Cu1A—O4W 2.599 (5) Cu1B—O3W 2.564 (5)
       
N1A—Cu1A—N2A 85.1 (2) N1B—Cu1B—N2B 84.8 (2)
N3A—Cu1A—N4A 85.2 (2) N3B—Cu1B—N4B 85.0 (2)
O4W—Cu1A—O1W 177.6 (2) O2W—Cu1B—O3W 176.3 (2)
[Figure 1]
Figure 1
The asymmetric unit of the title complex, showing the major component of the disorder only, with the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

The crystal structure displays an extensive hydrogen-bonding network (Table 2[link]). The crystal packing of the title compound (Fig. 2[link]) features N—H⋯O and O—H⋯O hydrogen bonds, which connect the cations and anions, forming layers parallel to (200). All four water ligands are involved in inter­molecular hydrogen bonds. In addition, there are ππ stacking inter­actions with a centroid–centroid distance of 3.812 (6) Å between rings (C1B–C6B) and (C1A–C6A) at ([{1\over 2}] + x, 1/2 – y, [{1\over 2}] + z). These inter­actions consolidate the three-dimensional structure (Fig. 2[link]).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1AA⋯O71B 0.91 1.98 2.881 (14) 172
N3A—H3AB⋯O72D 0.91 1.90 2.809 (11) 174
N1B—H1BB⋯O72C 0.91 1.99 2.902 (8) 174
N2B—H2BB⋯O72A 0.91 2.02 2.874 (12) 155
N3B—H3BA⋯O71A 0.91 1.89 2.795 (10) 176
O1W—H1WA⋯O72A 0.85 1.97 2.794 (13) 164
O1W—H1WB⋯O71D 0.85 1.94 2.763 (19) 162
O2W—H2WA⋯O71C 0.87 1.98 2.739 (9) 145
O2W—H2WB⋯O71Ci 1.07 1.78 2.803 (10) 160
O3W—H3WA⋯O71Dii 0.85 1.92 2.739 (15) 160
O3W—H3WB⋯O72A 0.85 2.04 2.750 (13) 141
O4W—H4WA⋯O72B 0.85 1.91 2.753 (12) 173
O4W—H4WB⋯O72Biii 0.85 1.90 2.726 (13) 164
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) x, y, z+1; (iii) [x, -y+1, z-{\script{1\over 2}}].
[Figure 2]
Figure 2
A view of the crystal packing of the title complex with only the major component of disorder shown and fine red dotted lines indicating hydrogen bonds (Table 2[link]). Displacement ellipsoids are drawn at the 50% probability level [symmetry codes: (i) x, 1 − y, −[{1\over 2}] + z; (ii) x, −y, [{1\over 2}] + z; (iii) [{1\over 2}] + x, [{1\over 2}] − y, [{1\over 2}] + z].

4. Hirshfeld surface analysis

In order to visualize the inter­molecular inter­actions in the crystal of the title compound, Hirshfeld surface analysis (Hirshfeld, 1977[Hirshfeld, H. L. (1977). Theor. Chim. Acta, 44, 129-138.]) was carried out by using CrystalExplorer17.5 (Turner et al., 2017[Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17.5. University of Western Australia. http://hirshfeldsurface.net.]). The Hirshfeld surface of the title complex plotted over dnorm is shown in Fig. 3[link] where the N—H⋯O and O—H⋯O hydrogen bonds are indicated by red spots. Selected two-dimensional fingerprint plots are shown in Fig. 4[link] for all contacts as well as individual O⋯H/H⋯O, H⋯H and C⋯H/H⋯C contacts, whose percentage contribution is also given. The small percentage contributions from the other different inter­atomic contacts to the Hirshfeld surface are as follows: C⋯C (2.9%), C⋯O/O⋯C (2.2%), N⋯H/H⋯N (0.9%) and N⋯O/O⋯N (0.3%).

[Figure 3]
Figure 3
View of the Hirshfeld surface mapped over dnorm in the range −0.6381 to +1.2243 (arbitrary units).
[Figure 4]
Figure 4
Hirshfeld surface fingerprint plots for the O⋯H/H⋯O, H⋯H and C⋯H/H⋯C contacts of the title complex.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update of February 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the title complex revealed two similar structures: di­aqua­bis­(ethane-1,2-di­amine)­copper(II) 5-chloro-2-nitro­benzoate dihydrate (JUMGOP; Saini et al., 2015[Saini, A., Sharma, R. P., Kumar, S., Venugopalan, P., Starynowicz, P. & Jezierska, J. (2015). Inorg. Chim. Acta, 436, 169-178.]) and trans-di­aqua­(1,3-di­amino­propane)­copper(II) 2-nitro­benzoate (WIFRUY; Sundberg & Klinga, 1994[Sundberg, M. R. & Klinga, M. (1994). Polyhedron, 13, 1099-1100.]). Both complexes have an octa­hedral coordination geometry at the metal center and the Cu—N and Cu—O bond lengths in these structure are comparable to those in the title compound.

6. Synthesis and crystallization

An aqueous solution of sodium 2-nitro­benzoate (20 mmol, 3.78 g) was added to an aqueous solution of CuSO4·5H2O (10 mmol, 2.5 g) under stirring. The precipitate was filtered, dried and dissolved in a hot methanol solution containing ethyl­enedi­amine (20 mmol, 1.2 g) under stirring. The mixture was filtered and single crystals were obtained after slow evaporation for one week.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 and 0.99 Å with Uiso(H) = 1.2Ueq(C) for all C-bound H atoms. The N-bound H atoms were located in a difference-Fourier map and refined with N—H = 0.91 Å, and with Uiso(H) = 1.5Ueq(N). The H atoms bonded to O atoms (O1W, O2W, O3W and O4W) were located in a difference map and treated as part of a rigid group with oxygen as the pivot atom. All four anions are whole-mol­ecule disordered over two sets of sites. The major components have refined occupancies of 0.572 (13), 0.591 (9), 0.601 (9) and 794 (10). The major and minor components of disorder for each anion were constrained using the SAME command in SHELXL (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]). The SIMU command was used to apply restraints to the displacement parameters of the atoms of the anions.

Table 3
Experimental details

Crystal data
Chemical formula [Cu(C2H8N2)2(H2O)2](C7H4NO4)2
Mr 552.00
Crystal system, space group Monoclinic, Cc
Temperature (K) 100
a, b, c (Å) 26.7742 (16), 20.8916 (14), 8.4254 (5)
β (°) 93.460 (3)
V3) 4704.2 (5)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.99
Crystal size (mm) 0.52 × 0.32 × 0.3
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.593, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 44253, 13693, 11671
Rint 0.038
(sin θ/λ)max−1) 0.746
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.138, 1.07
No. of reflections 13693
No. of parameters 1026
No. of restraints 1750
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.95, −0.86
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.49 (2)
Computer programs: APEX2and SAINT (Bruker, 2013[Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Diaquabis(ethylenediamine-κ2N,N')copper(II) bis(2-nitrobenzoate) top
Crystal data top
[Cu(C2H8N2)2(H2O)2](C7H4NO4)2F(000) = 2296
Mr = 552.00Dx = 1.559 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 26.7742 (16) ÅCell parameters from 9966 reflections
b = 20.8916 (14) Åθ = 3.0–32.0°
c = 8.4254 (5) ŵ = 0.99 mm1
β = 93.460 (3)°T = 100 K
V = 4704.2 (5) Å3Block, violet
Z = 80.52 × 0.32 × 0.3 mm
Data collection top
Bruker APEXII CCD
diffractometer
13693 independent reflections
Radiation source: sealed tube11671 reflections with I > 2σ(I)
Detector resolution: 8 pixels mm-1Rint = 0.038
φ and ω scansθmax = 32.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
h = 3639
Tmin = 0.593, Tmax = 0.746k = 3130
44253 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.0259P)2 + 37.9856P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.95 e Å3
13693 reflectionsΔρmin = 0.86 e Å3
1026 parametersAbsolute structure: Refined as an inversion twin
1750 restraintsAbsolute structure parameter: 0.49 (2)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.5784 (2)0.3461 (2)0.2462 (6)0.0126 (10)
H1AA0.5985990.3652560.3229800.015*
H1AB0.5803810.3029640.2604970.015*
Cu1A0.50809 (3)0.37528 (4)0.26174 (6)0.01011 (15)
N2A0.5082 (2)0.3874 (3)0.0210 (6)0.0126 (10)
H2AA0.4793640.3718580.0271000.015*
H2AB0.5106260.4297070.0030590.015*
N3A0.4375 (2)0.4064 (2)0.2787 (6)0.0117 (10)
H3AA0.4363020.4497440.2686000.014*
H3AB0.4171250.3888980.1998950.014*
N4A0.5077 (2)0.3610 (3)0.4985 (6)0.0111 (9)
H4AA0.5049220.3184070.5194110.013*
H4AB0.5367090.3755010.5473330.013*
C11A0.5949 (3)0.3633 (4)0.0863 (9)0.0162 (13)
H11A0.6238990.3366460.0605650.019*
H11B0.6051940.4088130.0848180.019*
C12A0.5518 (2)0.3521 (3)0.0344 (7)0.0118 (10)
H12A0.5603150.3678890.1402320.014*
H12B0.5441700.3057980.0429890.014*
C13A0.4207 (3)0.3872 (4)0.4358 (9)0.0145 (12)
H13A0.4096860.3419550.4329680.017*
H13B0.3921680.4141620.4642800.017*
C14A0.4648 (2)0.3958 (3)0.5584 (7)0.0147 (11)
H14A0.4729470.4417650.5717340.018*
H14B0.4562970.3783100.6625880.018*
C1D0.3508 (2)0.3417 (3)0.2268 (7)0.0171 (4)0.572 (13)
C2D0.3305 (5)0.3975 (4)0.2818 (15)0.0177 (5)0.572 (13)
C3D0.2951 (4)0.4012 (6)0.4118 (13)0.0180 (5)0.572 (13)
H3D0.2811730.4411780.4451400.022*0.572 (13)
C4D0.2814 (4)0.3459 (7)0.4887 (12)0.0179 (6)0.572 (13)
H4D0.2569000.3471130.5750550.021*0.572 (13)
C5D0.3017 (4)0.2907 (6)0.4444 (12)0.0177 (6)0.572 (13)
H5D0.2924270.2531160.5024160.021*0.572 (13)
C6D0.3366 (5)0.2860 (5)0.3142 (13)0.0175 (5)0.572 (13)
H6D0.3507250.2456590.2846580.021*0.572 (13)
C7D0.3826 (2)0.3304 (3)0.0777 (7)0.0165 (4)0.572 (13)
N8D0.3502 (4)0.4560 (4)0.2127 (12)0.0181 (6)0.572 (13)
O71D0.4229 (6)0.2993 (13)0.096 (2)0.0165 (9)0.572 (13)
O72D0.3693 (4)0.3535 (7)0.0484 (12)0.0155 (9)0.572 (13)
O81D0.3947 (3)0.4573 (5)0.1649 (12)0.0191 (10)0.572 (13)
O82D0.3215 (3)0.5017 (4)0.2149 (12)0.0208 (10)0.572 (13)
C1E0.3508 (2)0.3417 (3)0.2268 (7)0.0171 (4)0.428 (13)
C2E0.3347 (7)0.4043 (5)0.263 (2)0.0177 (5)0.428 (13)
C3E0.3013 (5)0.4194 (7)0.3942 (16)0.0178 (6)0.428 (13)
H3E0.2907270.4622770.4123750.021*0.428 (13)
C4E0.2844 (5)0.3710 (8)0.4958 (15)0.0179 (6)0.428 (13)
H4E0.2625880.3802410.5861080.021*0.428 (13)
C5E0.2989 (5)0.3119 (8)0.4652 (16)0.0177 (6)0.428 (13)
H5E0.2867540.2785590.5339190.021*0.428 (13)
C6E0.3315 (6)0.2964 (6)0.3355 (17)0.0175 (5)0.428 (13)
H6E0.3410440.2528870.3205930.021*0.428 (13)
C7E0.3826 (2)0.3304 (3)0.0777 (7)0.0165 (4)0.428 (13)
N8E0.3549 (5)0.4602 (6)0.1759 (17)0.0182 (6)0.428 (13)
O71E0.4244 (8)0.3014 (17)0.085 (3)0.0165 (10)0.428 (13)
O72E0.3622 (5)0.3489 (10)0.0442 (16)0.0156 (10)0.428 (13)
O81E0.3978 (4)0.4578 (7)0.1178 (15)0.0185 (10)0.428 (13)
O82E0.3282 (5)0.5073 (5)0.1606 (16)0.0203 (10)0.428 (13)
N1B0.5666 (2)0.1555 (3)0.7183 (6)0.0148 (10)
H1BA0.5675450.1990050.7206570.018*
H1BB0.5872030.1403280.7995730.018*
Cu1B0.49668 (3)0.12486 (4)0.74192 (6)0.01311 (18)
N2B0.4957 (2)0.1094 (3)0.5015 (6)0.0140 (10)
H2BA0.4962620.0666840.4805380.017*
H2BB0.4674560.1263680.4526220.017*
N3B0.4264 (2)0.0950 (3)0.7658 (6)0.0141 (10)
H3BA0.4057170.1118280.6868880.017*
H3BB0.4249480.0515830.7585590.017*
N4B0.4984 (2)0.1396 (3)0.9805 (6)0.0136 (10)
H4BA0.5271410.1233261.0278030.016*
H4BB0.4972200.1822171.0019130.016*
C11B0.5830 (3)0.1318 (3)0.5646 (9)0.0154 (13)
H11C0.5917970.0858520.5730450.019*
H11D0.6128880.1557620.5344590.019*
C12B0.5411 (3)0.1412 (3)0.4428 (7)0.0171 (13)
H12C0.5496690.1220340.3403880.021*
H12D0.5347520.1874390.4258880.021*
C13B0.4103 (3)0.1158 (4)0.9221 (9)0.0161 (13)
H13C0.3816760.0896730.9533690.019*
H13D0.3998890.1613050.9178180.019*
C14B0.4548 (3)0.1071 (4)1.0404 (8)0.0221 (14)
H14C0.4470850.1252921.1445950.027*
H14D0.4620080.0609041.0550280.027*
C1B0.6625 (2)0.4018 (2)0.7429 (6)0.0102 (4)0.591 (19)
C2B0.6758 (2)0.3377 (2)0.7682 (6)0.0106 (4)0.591 (19)
C3B0.7066 (4)0.3136 (4)0.8906 (10)0.0107 (5)0.591 (19)
H3B0.7131140.2690870.9011140.013*0.591 (19)
C4B0.7276 (4)0.3579 (5)0.9978 (10)0.0108 (5)0.591 (19)
H4B0.7504580.3445031.0817970.013*0.591 (19)
C5B0.7145 (4)0.4224 (5)0.9804 (11)0.0107 (5)0.591 (19)
H5B0.7281210.4524871.0557350.013*0.591 (19)
C6B0.6825 (5)0.4438 (4)0.8574 (12)0.0106 (5)0.591 (19)
H6B0.6740710.4879550.8508700.013*0.591 (19)
C7B0.6310 (7)0.4229 (13)0.5960 (10)0.0102 (5)0.591 (19)
N8B0.6529 (4)0.2899 (4)0.6573 (11)0.0111 (5)0.591 (19)
O71B0.6474 (5)0.4129 (6)0.4634 (13)0.0105 (9)0.591 (19)
O72B0.5899 (4)0.4499 (6)0.6186 (14)0.0098 (9)0.591 (19)
O81B0.6092 (4)0.2968 (6)0.6063 (12)0.0109 (9)0.591 (19)
O82B0.6781 (3)0.2426 (4)0.6213 (12)0.0131 (9)0.591 (19)
C1G0.6625 (2)0.4018 (2)0.7429 (6)0.0102 (4)0.409 (19)
C2G0.6758 (2)0.3377 (2)0.7682 (6)0.0106 (4)0.409 (19)
C3G0.7112 (6)0.3263 (7)0.8914 (15)0.0108 (5)0.409 (19)
H3G0.7231050.2839230.9098900.013*0.409 (19)
C4G0.7297 (5)0.3758 (7)0.9888 (16)0.0110 (5)0.409 (19)
H4G0.7544180.3660331.0708510.013*0.409 (19)
C5G0.7137 (6)0.4388 (7)0.9714 (16)0.0108 (5)0.409 (19)
H5G0.7250740.4715681.0429730.013*0.409 (19)
C6G0.6801 (8)0.4509 (5)0.8428 (18)0.0105 (5)0.409 (19)
H6G0.6689330.4934660.8228250.013*0.409 (19)
C7G0.6322 (10)0.4214 (18)0.5917 (14)0.0101 (5)0.409 (19)
N8G0.6527 (5)0.2851 (5)0.6764 (16)0.0111 (5)0.409 (19)
O71G0.6525 (7)0.4050 (8)0.4693 (18)0.0103 (10)0.409 (19)
O72G0.5939 (6)0.4560 (8)0.603 (2)0.0097 (10)0.409 (19)
O81G0.6082 (5)0.2910 (9)0.6290 (18)0.0112 (10)0.409 (19)
O82G0.6783 (4)0.2361 (5)0.6735 (18)0.0128 (10)0.409 (19)
C1A0.3417 (2)0.1623 (2)0.2578 (6)0.0152 (4)0.601 (9)
C2A0.3179 (5)0.1062 (4)0.2068 (14)0.0158 (5)0.601 (9)
C3A0.2819 (4)0.1031 (5)0.0828 (11)0.0157 (6)0.601 (9)
H3A0.2658870.0638680.0536600.019*0.601 (9)
C4A0.2702 (4)0.1593 (5)0.0027 (11)0.0159 (6)0.601 (9)
H4A0.2454080.1590140.0830110.019*0.601 (9)
C5A0.2941 (4)0.2164 (5)0.0459 (11)0.0157 (6)0.601 (9)
H5A0.2861640.2544080.0121460.019*0.601 (9)
C6A0.3296 (5)0.2183 (4)0.1730 (12)0.0154 (5)0.601 (9)
H6A0.3455300.2575560.2023000.018*0.601 (9)
C7A0.3746 (5)0.1699 (8)0.4095 (10)0.0153 (6)0.601 (9)
N8A0.3354 (3)0.0455 (4)0.2762 (11)0.0171 (6)0.601 (9)
O71A0.3590 (4)0.1453 (4)0.5321 (10)0.0160 (9)0.601 (9)
O72A0.4171 (4)0.1964 (5)0.3989 (16)0.0155 (10)0.601 (9)
O81A0.3057 (3)0.0005 (3)0.2881 (11)0.0202 (9)0.601 (9)
O82A0.3802 (3)0.0417 (4)0.3236 (10)0.0193 (9)0.601 (9)
C1F0.3417 (2)0.1623 (2)0.2578 (6)0.0152 (4)0.399 (9)
C2F0.3231 (7)0.1000 (4)0.225 (2)0.0159 (5)0.399 (9)
C3F0.2893 (6)0.0852 (7)0.0989 (16)0.0159 (6)0.399 (9)
H3F0.2773810.0427280.0833860.019*0.399 (9)
C4F0.2734 (6)0.1340 (7)0.0043 (16)0.0159 (6)0.399 (9)
H4F0.2507950.1253020.0929630.019*0.399 (9)
C5F0.2910 (6)0.1957 (7)0.0244 (16)0.0157 (6)0.399 (9)
H5F0.2793480.2293310.0441190.019*0.399 (9)
C6F0.3252 (7)0.2097 (6)0.1502 (17)0.0154 (6)0.399 (9)
H6F0.3375210.2521870.1632070.018*0.399 (9)
C7F0.3737 (7)0.1752 (12)0.4088 (13)0.0153 (6)0.399 (9)
N8F0.3431 (4)0.0451 (5)0.3204 (16)0.0169 (6)0.399 (9)
O71F0.3543 (5)0.1626 (6)0.5361 (15)0.0152 (10)0.399 (9)
O72F0.4133 (6)0.2073 (7)0.393 (2)0.0154 (10)0.399 (9)
O81F0.3166 (4)0.0008 (5)0.3512 (16)0.0190 (9)0.399 (9)
O82F0.3868 (4)0.0483 (6)0.3765 (15)0.0187 (10)0.399 (9)
C1C0.6565 (2)0.0820 (2)1.2352 (7)0.0121 (4)0.794 (10)
C2C0.6821 (3)0.1344 (3)1.3002 (9)0.0125 (5)0.794 (10)
C3C0.7183 (3)0.1298 (3)1.4243 (8)0.0126 (5)0.794 (10)
H3C0.7349270.1670921.4648200.015*0.794 (10)
C4C0.7299 (3)0.0706 (4)1.4880 (8)0.0126 (5)0.794 (10)
H4C0.7550420.0660971.5717900.015*0.794 (10)
C5C0.7036 (3)0.0167 (3)1.4261 (8)0.0124 (5)0.794 (10)
H5C0.7105920.0243181.4708130.015*0.794 (10)
C6C0.6679 (4)0.0225 (3)1.3015 (9)0.0121 (5)0.794 (10)
H6C0.6509970.0144991.2608190.014*0.794 (10)
C7C0.6219 (4)0.0840 (7)1.0855 (12)0.0123 (5)0.794 (10)
N8C0.6677 (3)0.1993 (3)1.2447 (8)0.0133 (5)0.794 (10)
O71C0.5823 (3)0.0503 (3)1.0884 (10)0.0129 (9)0.794 (10)
O72C0.6380 (3)0.1118 (3)0.9677 (8)0.0142 (9)0.794 (10)
O81C0.6224 (2)0.2084 (2)1.2129 (7)0.0151 (8)0.794 (10)
O82C0.7004 (2)0.2407 (2)1.2412 (7)0.0172 (8)0.794 (10)
C1H0.6565 (2)0.0820 (2)1.2352 (7)0.0121 (4)0.206 (10)
C2H0.6740 (11)0.1416 (6)1.285 (3)0.0126 (5)0.206 (10)
C3H0.7100 (10)0.1454 (11)1.409 (3)0.0126 (5)0.206 (10)
H3H0.7253960.1853761.4335050.015*0.206 (10)
C4H0.7237 (10)0.0926 (12)1.497 (3)0.0126 (6)0.206 (10)
H4H0.7466430.0963251.5866910.015*0.206 (10)
C5H0.7034 (11)0.0325 (11)1.451 (3)0.0124 (6)0.206 (10)
H5H0.7131710.0046121.5104620.015*0.206 (10)
C6H0.6692 (15)0.0272 (8)1.321 (4)0.0122 (5)0.206 (10)
H6H0.6548640.0130131.2913860.015*0.206 (10)
C7H0.6201 (15)0.082 (3)1.088 (4)0.0124 (5)0.206 (10)
N8H0.6538 (8)0.2019 (8)1.211 (3)0.0135 (6)0.206 (10)
O71H0.5758 (9)0.0596 (13)1.097 (4)0.0124 (10)0.206 (10)
O72H0.6288 (10)0.1206 (12)0.978 (3)0.0128 (10)0.206 (10)
O81H0.6090 (8)0.2047 (10)1.160 (3)0.0144 (10)0.206 (10)
O82H0.6831 (9)0.2480 (9)1.210 (3)0.0151 (9)0.206 (10)
O1W0.47408 (19)0.2612 (2)0.1831 (6)0.0168 (10)
H1WA0.4610640.2355580.2471760.025*
H1WB0.4528280.2701770.1074840.025*
O2W0.52864 (19)0.0129 (2)0.8172 (6)0.0156 (9)
H2WA0.5517090.0344050.8721220.023*
H2WB0.5556030.0042570.7395090.023*
O3W0.47048 (19)0.2395 (2)0.6668 (6)0.0154 (9)
H3WA0.4576330.2660810.7288230.023*
H3WB0.4436930.2363960.6082470.023*
O4W0.53815 (18)0.4895 (2)0.3438 (5)0.0133 (9)
H4WA0.5539130.4804660.4314160.020*
H4WB0.5586110.5032530.2783340.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.017 (3)0.013 (2)0.009 (2)0.0022 (18)0.0027 (17)0.0001 (16)
Cu1A0.0101 (4)0.0129 (3)0.0077 (3)0.0029 (2)0.0033 (3)0.00127 (19)
N2A0.012 (2)0.014 (2)0.012 (2)0.000 (2)0.0029 (18)0.0035 (19)
N3A0.013 (2)0.013 (2)0.009 (2)0.0027 (17)0.0003 (17)0.0020 (16)
N4A0.010 (2)0.012 (2)0.012 (2)0.0010 (19)0.0023 (17)0.0009 (18)
C11A0.015 (3)0.019 (3)0.015 (3)0.001 (2)0.003 (2)0.003 (2)
C12A0.008 (2)0.019 (3)0.008 (2)0.004 (2)0.0043 (18)0.001 (2)
C13A0.011 (3)0.017 (3)0.016 (3)0.003 (2)0.007 (2)0.002 (2)
C14A0.012 (3)0.022 (3)0.010 (2)0.002 (2)0.0011 (19)0.002 (2)
C1D0.0134 (7)0.0233 (8)0.0143 (7)0.0031 (7)0.0007 (7)0.0010 (7)
C2D0.0137 (9)0.0239 (9)0.0151 (9)0.0026 (9)0.0010 (9)0.0005 (9)
C3D0.0137 (10)0.0243 (11)0.0157 (10)0.0028 (10)0.0012 (9)0.0008 (10)
C4D0.0134 (11)0.0242 (11)0.0158 (11)0.0031 (11)0.0016 (10)0.0011 (11)
C5D0.0134 (10)0.0241 (11)0.0154 (10)0.0030 (10)0.0016 (10)0.0010 (10)
C6D0.0134 (10)0.0239 (10)0.0149 (10)0.0031 (9)0.0011 (9)0.0010 (9)
C7D0.0137 (8)0.0219 (8)0.0135 (8)0.0031 (7)0.0007 (7)0.0014 (7)
N8D0.0145 (11)0.0238 (11)0.0158 (12)0.0016 (10)0.0010 (11)0.0003 (11)
O71D0.0142 (16)0.0215 (17)0.0137 (17)0.0022 (15)0.0000 (15)0.0023 (16)
O72D0.0141 (18)0.0201 (17)0.0121 (15)0.0014 (17)0.0014 (15)0.0031 (14)
O81D0.0166 (17)0.0225 (17)0.0177 (19)0.0033 (16)0.0034 (18)0.0004 (18)
O82D0.0174 (17)0.0260 (17)0.0187 (19)0.0022 (16)0.0016 (17)0.0008 (18)
C1E0.0134 (7)0.0233 (8)0.0143 (7)0.0031 (7)0.0007 (7)0.0010 (7)
C2E0.0137 (9)0.0239 (9)0.0152 (9)0.0026 (9)0.0010 (9)0.0005 (9)
C3E0.0135 (10)0.0242 (11)0.0156 (10)0.0027 (10)0.0013 (10)0.0008 (10)
C4E0.0134 (11)0.0244 (11)0.0156 (11)0.0028 (11)0.0015 (10)0.0008 (11)
C5E0.0134 (10)0.0241 (11)0.0153 (10)0.0031 (10)0.0014 (9)0.0009 (10)
C6E0.0134 (10)0.0239 (10)0.0148 (10)0.0031 (10)0.0010 (9)0.0009 (10)
C7E0.0137 (8)0.0219 (8)0.0135 (8)0.0031 (7)0.0007 (7)0.0014 (7)
N8E0.0146 (11)0.0238 (11)0.0160 (12)0.0017 (10)0.0009 (11)0.0000 (11)
O71E0.0143 (17)0.0215 (17)0.0136 (18)0.0022 (16)0.0001 (16)0.0021 (16)
O72E0.0142 (18)0.0201 (17)0.0122 (16)0.0024 (17)0.0009 (16)0.0027 (15)
O81E0.0157 (18)0.0229 (17)0.016 (2)0.0028 (17)0.0025 (19)0.0005 (19)
O82E0.0169 (18)0.0256 (18)0.0181 (19)0.0017 (17)0.0011 (18)0.0008 (19)
N1B0.022 (3)0.012 (2)0.012 (2)0.0015 (19)0.0041 (19)0.0002 (16)
Cu1B0.0176 (5)0.0136 (3)0.0087 (4)0.0001 (2)0.0056 (3)0.0000 (2)
N2B0.018 (3)0.016 (2)0.008 (2)0.001 (2)0.0033 (18)0.0025 (19)
N3B0.017 (3)0.013 (2)0.014 (2)0.0024 (18)0.0077 (18)0.0003 (17)
N4B0.021 (3)0.011 (2)0.009 (2)0.003 (2)0.0010 (18)0.0019 (18)
C11B0.018 (3)0.016 (3)0.013 (3)0.000 (2)0.007 (2)0.003 (2)
C12B0.031 (4)0.011 (3)0.010 (2)0.000 (2)0.008 (2)0.001 (2)
C13B0.017 (3)0.019 (3)0.014 (3)0.003 (2)0.008 (2)0.002 (2)
C14B0.033 (4)0.020 (3)0.015 (3)0.003 (3)0.012 (3)0.002 (2)
C1B0.0092 (7)0.0119 (7)0.0095 (7)0.0040 (6)0.0003 (6)0.0026 (6)
C2B0.0096 (7)0.0119 (7)0.0101 (7)0.0043 (6)0.0003 (6)0.0026 (6)
C3B0.0097 (9)0.0118 (10)0.0106 (9)0.0041 (9)0.0001 (8)0.0031 (9)
C4B0.0099 (9)0.0118 (11)0.0106 (9)0.0041 (10)0.0002 (9)0.0035 (10)
C5B0.0097 (9)0.0119 (10)0.0104 (9)0.0043 (10)0.0001 (9)0.0034 (10)
C6B0.0095 (9)0.0120 (10)0.0101 (9)0.0041 (9)0.0004 (8)0.0029 (9)
C7B0.0092 (10)0.0118 (10)0.0094 (9)0.0036 (9)0.0002 (9)0.0025 (9)
N8B0.0108 (9)0.0120 (10)0.0105 (10)0.0040 (9)0.0006 (9)0.0026 (9)
O71B0.0099 (18)0.0122 (18)0.0094 (15)0.0045 (15)0.0008 (15)0.0018 (15)
O72B0.0082 (16)0.0122 (17)0.0086 (17)0.0032 (15)0.0018 (15)0.0031 (15)
O81B0.0097 (15)0.0121 (17)0.0108 (18)0.0013 (14)0.0018 (15)0.0034 (16)
O82B0.0140 (16)0.0132 (16)0.0122 (18)0.0065 (14)0.0010 (17)0.0018 (16)
C1G0.0092 (7)0.0119 (7)0.0095 (7)0.0040 (6)0.0003 (6)0.0026 (6)
C2G0.0096 (7)0.0119 (7)0.0101 (7)0.0043 (6)0.0003 (6)0.0026 (6)
C3G0.0099 (9)0.0118 (10)0.0107 (9)0.0043 (9)0.0001 (8)0.0030 (9)
C4G0.0100 (10)0.0120 (11)0.0108 (9)0.0043 (10)0.0000 (9)0.0034 (10)
C5G0.0098 (10)0.0119 (11)0.0105 (9)0.0043 (10)0.0000 (9)0.0034 (10)
C6G0.0095 (9)0.0120 (10)0.0101 (9)0.0042 (9)0.0003 (8)0.0031 (9)
C7G0.0092 (10)0.0118 (10)0.0094 (9)0.0037 (9)0.0002 (9)0.0025 (9)
N8G0.0107 (9)0.0120 (10)0.0106 (10)0.0041 (9)0.0004 (9)0.0026 (9)
O71G0.0098 (18)0.0120 (19)0.0091 (16)0.0047 (17)0.0008 (16)0.0021 (16)
O72G0.0078 (17)0.0124 (18)0.0086 (18)0.0028 (16)0.0013 (16)0.0028 (16)
O81G0.0105 (16)0.0123 (18)0.0101 (19)0.0023 (16)0.0030 (17)0.0037 (17)
O82G0.0135 (17)0.0127 (17)0.0120 (19)0.0061 (16)0.0003 (18)0.0025 (17)
C1A0.0139 (8)0.0167 (9)0.0152 (8)0.0021 (8)0.0027 (7)0.0013 (8)
C2A0.0145 (10)0.0171 (10)0.0162 (10)0.0021 (9)0.0028 (9)0.0010 (9)
C3A0.0141 (11)0.0174 (11)0.0158 (10)0.0023 (10)0.0025 (10)0.0011 (10)
C4A0.0143 (11)0.0177 (12)0.0158 (11)0.0025 (11)0.0027 (10)0.0014 (11)
C5A0.0142 (11)0.0174 (12)0.0158 (11)0.0024 (11)0.0028 (10)0.0016 (10)
C6A0.0140 (10)0.0170 (11)0.0153 (10)0.0023 (10)0.0029 (9)0.0015 (10)
C7A0.0143 (11)0.0167 (12)0.0150 (10)0.0018 (10)0.0023 (9)0.0014 (10)
N8A0.0159 (11)0.0176 (11)0.0180 (12)0.0019 (10)0.0022 (10)0.0006 (11)
O71A0.0163 (17)0.0181 (19)0.0137 (15)0.0012 (17)0.0013 (15)0.0026 (17)
O72A0.0138 (17)0.0167 (19)0.0160 (16)0.0003 (17)0.0017 (15)0.0011 (17)
O81A0.0197 (18)0.0190 (16)0.0218 (18)0.0011 (16)0.0009 (17)0.0018 (17)
O82A0.0178 (16)0.0184 (15)0.0215 (17)0.0037 (15)0.0005 (16)0.0005 (16)
C1F0.0139 (8)0.0167 (9)0.0152 (8)0.0021 (8)0.0027 (7)0.0013 (8)
C2F0.0145 (10)0.0172 (10)0.0161 (10)0.0020 (9)0.0027 (9)0.0009 (9)
C3F0.0145 (11)0.0175 (11)0.0160 (11)0.0019 (10)0.0028 (10)0.0011 (10)
C4F0.0144 (11)0.0175 (12)0.0159 (11)0.0020 (11)0.0027 (10)0.0013 (11)
C5F0.0143 (11)0.0174 (12)0.0156 (11)0.0022 (11)0.0028 (10)0.0014 (11)
C6F0.0141 (10)0.0170 (11)0.0154 (10)0.0021 (10)0.0028 (9)0.0014 (10)
C7F0.0143 (11)0.0167 (12)0.0150 (10)0.0019 (10)0.0023 (9)0.0013 (10)
N8F0.0158 (12)0.0174 (11)0.0177 (12)0.0018 (10)0.0025 (11)0.0006 (11)
O71F0.0152 (18)0.017 (2)0.0137 (16)0.0029 (18)0.0028 (16)0.0014 (18)
O72F0.0139 (18)0.016 (2)0.0159 (17)0.0012 (18)0.0017 (16)0.0013 (18)
O81F0.0180 (17)0.0185 (16)0.0206 (18)0.0004 (16)0.0024 (16)0.0011 (17)
O82F0.0183 (18)0.0184 (18)0.0196 (19)0.0045 (17)0.0023 (18)0.0002 (18)
C1C0.0137 (8)0.0106 (7)0.0120 (7)0.0051 (7)0.0002 (7)0.0010 (6)
C2C0.0139 (10)0.0106 (8)0.0129 (9)0.0055 (8)0.0003 (8)0.0009 (8)
C3C0.0138 (10)0.0109 (10)0.0128 (9)0.0057 (9)0.0002 (9)0.0004 (9)
C4C0.0137 (11)0.0112 (10)0.0129 (10)0.0055 (10)0.0001 (9)0.0004 (9)
C5C0.0134 (10)0.0111 (10)0.0126 (10)0.0052 (10)0.0001 (9)0.0006 (9)
C6C0.0134 (10)0.0107 (9)0.0120 (9)0.0048 (9)0.0000 (9)0.0009 (9)
C7C0.0146 (11)0.0105 (10)0.0116 (9)0.0048 (9)0.0001 (9)0.0011 (9)
N8C0.0143 (11)0.0110 (10)0.0141 (10)0.0056 (9)0.0020 (9)0.0008 (9)
O71C0.0163 (17)0.0111 (17)0.0112 (15)0.0028 (14)0.0004 (14)0.0008 (14)
O72C0.0175 (18)0.0132 (16)0.0120 (14)0.0039 (14)0.0018 (14)0.0032 (13)
O81C0.0155 (16)0.0121 (13)0.0169 (15)0.0071 (13)0.0051 (14)0.0013 (13)
O82C0.0166 (17)0.0137 (14)0.0206 (16)0.0035 (14)0.0049 (14)0.0030 (13)
C1H0.0137 (8)0.0106 (7)0.0120 (7)0.0051 (7)0.0002 (7)0.0010 (6)
C2H0.0139 (10)0.0108 (9)0.0130 (9)0.0055 (8)0.0005 (8)0.0009 (8)
C3H0.0139 (11)0.0109 (10)0.0129 (10)0.0055 (10)0.0002 (9)0.0007 (9)
C4H0.0138 (11)0.0110 (11)0.0129 (10)0.0054 (10)0.0001 (10)0.0005 (10)
C5H0.0136 (11)0.0109 (10)0.0125 (10)0.0052 (10)0.0000 (9)0.0007 (10)
C6H0.0135 (10)0.0107 (10)0.0122 (10)0.0050 (9)0.0001 (9)0.0008 (9)
C7H0.0145 (11)0.0107 (10)0.0117 (10)0.0048 (9)0.0003 (9)0.0012 (9)
N8H0.0144 (12)0.0112 (10)0.0145 (11)0.0054 (10)0.0015 (10)0.0010 (10)
O71H0.0151 (19)0.0105 (19)0.0114 (17)0.0045 (18)0.0002 (17)0.0007 (17)
O72H0.0153 (19)0.0113 (18)0.0118 (17)0.0051 (18)0.0017 (18)0.0016 (17)
O81H0.0151 (19)0.0116 (18)0.0159 (19)0.0066 (18)0.0030 (18)0.0004 (18)
O82H0.0154 (18)0.0126 (16)0.0167 (17)0.0047 (16)0.0033 (16)0.0022 (16)
O1W0.013 (2)0.019 (2)0.018 (2)0.0011 (17)0.0015 (17)0.0087 (16)
O2W0.018 (2)0.014 (2)0.015 (2)0.0025 (17)0.0007 (17)0.0002 (15)
O3W0.014 (2)0.014 (2)0.018 (2)0.0018 (16)0.0006 (16)0.0010 (15)
O4W0.011 (2)0.017 (2)0.0113 (18)0.0006 (16)0.0011 (15)0.0043 (15)
Geometric parameters (Å, º) top
N1A—H1AA0.9100C4B—C5B1.399 (8)
N1A—H1AB0.9100C5B—H5B0.9500
N1A—Cu1A1.991 (6)C5B—C6B1.379 (8)
N1A—C11A1.487 (9)C6B—H6B0.9500
Cu1A—N2A2.044 (5)C7B—O71B1.242 (8)
Cu1A—N3A2.012 (6)C7B—O72B1.261 (8)
Cu1A—N4A2.017 (5)N8B—O81B1.231 (8)
Cu1A—O1W2.621 (5)N8B—O82B1.244 (8)
Cu1A—O4W2.599 (5)C1G—C2G1.400 (5)
N2A—H2AA0.9100C1G—C6G1.391 (8)
N2A—H2AB0.9100C1G—C7G1.524 (9)
N2A—C12A1.480 (9)C2G—C3G1.383 (8)
N3A—H3AA0.9100C2G—N8G1.459 (9)
N3A—H3AB0.9100C3G—H3G0.9500
N3A—C13A1.479 (9)C3G—C4G1.393 (9)
N4A—H4AA0.9100C4G—H4G0.9500
N4A—H4AB0.9100C4G—C5G1.389 (10)
N4A—C14A1.474 (9)C5G—H5G0.9500
C11A—H11A0.9900C5G—C6G1.389 (9)
C11A—H11B0.9900C6G—H6G0.9500
C11A—C12A1.510 (9)C7G—O71G1.243 (9)
C12A—H12A0.9900C7G—O72G1.263 (9)
C12A—H12B0.9900N8G—O81G1.239 (9)
C13A—H13A0.9900N8G—O82G1.235 (9)
C13A—H13B0.9900C1A—C2A1.390 (8)
C13A—C14A1.531 (9)C1A—C6A1.400 (8)
C14A—H14A0.9900C1A—C7A1.517 (8)
C14A—H14B0.9900C2A—C3A1.379 (9)
C1D—C2D1.357 (10)C2A—N8A1.463 (9)
C1D—C6D1.416 (10)C3A—H3A0.9500
C1D—C7D1.492 (8)C3A—C4A1.382 (10)
C2D—C3D1.407 (10)C4A—H4A0.9500
C2D—N8D1.439 (11)C4A—C5A1.393 (10)
C3D—H3D0.9500C5A—H5A0.9500
C3D—C4D1.366 (14)C5A—C6A1.387 (9)
C4D—H4D0.9500C6A—H6A0.9500
C4D—C5D1.319 (14)C7A—O71A1.249 (8)
C5D—H5D0.9500C7A—O72A1.271 (8)
C5D—C6D1.402 (11)N8A—O81A1.239 (8)
C6D—H6D0.9500N8A—O82A1.244 (8)
C7D—O71D1.277 (10)C1F—C2F1.414 (9)
C7D—O72D1.238 (9)C1F—C6F1.398 (9)
N8D—O81D1.234 (9)C1F—C7F1.514 (9)
N8D—O82D1.225 (9)C2F—C3F1.390 (10)
C1E—C2E1.405 (11)C2F—N8F1.480 (10)
C1E—C6E1.395 (11)C3F—H3F0.9500
C1E—C7E1.492 (8)C3F—C4F1.390 (11)
C2E—C3E1.414 (12)C4F—H4F0.9500
C2E—N8E1.467 (12)C4F—C5F1.389 (12)
C3E—H3E0.9500C5F—H5F0.9500
C3E—C4E1.385 (15)C5F—C6F1.389 (10)
C4E—H4E0.9500C6F—H6F0.9500
C4E—C5E1.315 (16)C7F—O71F1.247 (9)
C5E—H5E0.9500C7F—O72F1.268 (9)
C5E—C6E1.395 (13)N8F—O81F1.231 (10)
C6E—H6E0.9500N8F—O82F1.238 (10)
C7E—O71E1.277 (11)C1C—C2C1.386 (8)
C7E—O72E1.252 (11)C1C—C6C1.388 (7)
N8E—O81E1.223 (11)C1C—C7C1.519 (8)
N8E—O82E1.226 (11)C2C—C3C1.386 (9)
N1B—H1BA0.9100C2C—N8C1.479 (8)
N1B—H1BB0.9100C3C—H3C0.9500
N1B—Cu1B1.999 (6)C3C—C4C1.377 (9)
N1B—C11B1.478 (9)C4C—H4C0.9500
Cu1B—N2B2.050 (5)C4C—C5C1.411 (10)
Cu1B—N3B2.004 (6)C5C—H5C0.9500
Cu1B—N4B2.031 (5)C5C—C6C1.382 (8)
Cu1B—O2W2.557 (5)C6C—H6C0.9500
Cu1B—O3W2.564 (5)C7C—O71C1.275 (8)
N2B—H2BA0.9100C7C—O72C1.249 (8)
N2B—H2BB0.9100N8C—O81C1.239 (8)
N2B—C12B1.497 (9)N8C—O82C1.233 (8)
N3B—H3BA0.9100C1H—C2H1.386 (13)
N3B—H3BB0.9100C1H—C6H1.385 (13)
N3B—C13B1.475 (9)C1H—C7H1.529 (13)
N4B—H4BA0.9100C2H—C3H1.380 (14)
N4B—H4BB0.9100C2H—N8H1.490 (14)
N4B—C14B1.468 (10)C3H—H3H0.9500
C11B—H11C0.9900C3H—C4H1.366 (16)
C11B—H11D0.9900C4H—H4H0.9500
C11B—C12B1.487 (10)C4H—C5H1.412 (15)
C12B—H12C0.9900C5H—H5H0.9500
C12B—H12D0.9900C5H—C6H1.393 (14)
C13B—H13C0.9900C6H—H6H0.9500
C13B—H13D0.9900C7H—O71H1.281 (14)
C13B—C14B1.517 (11)C7H—O72H1.260 (14)
C14B—H14C0.9900N8H—O81H1.251 (15)
C14B—H14D0.9900N8H—O82H1.242 (14)
C1B—C2B1.400 (5)O1W—H1WA0.8505
C1B—C6B1.388 (7)O1W—H1WB0.8491
C1B—C7B1.521 (8)O2W—H2WA0.8734
C2B—C3B1.375 (7)O2W—H2WB1.0656
C2B—N8B1.475 (8)O3W—H3WA0.8500
C3B—H3B0.9500O3W—H3WB0.8478
C3B—C4B1.387 (8)O4W—H4WA0.8497
C4B—H4B0.9500O4W—H4WB0.8500
H1AA—N1A—H1AB108.4H13C—C13B—H13D108.6
Cu1A—N1A—H1AA110.0C14B—C13B—H13C110.3
Cu1A—N1A—H1AB110.0C14B—C13B—H13D110.3
C11A—N1A—H1AA110.0N4B—C14B—C13B109.1 (6)
C11A—N1A—H1AB110.0N4B—C14B—H14C109.9
C11A—N1A—Cu1A108.6 (4)N4B—C14B—H14D109.9
N1A—Cu1A—N2A85.1 (2)C13B—C14B—H14C109.9
N1A—Cu1A—N3A178.9 (2)C13B—C14B—H14D109.9
N1A—Cu1A—N4A94.7 (2)H14C—C14B—H14D108.3
N1A—Cu1A—O1W91.18 (19)C2B—C1B—C7B121.7 (11)
N1A—Cu1A—O4W91.14 (19)C6B—C1B—C2B114.5 (5)
N2A—Cu1A—O1W83.3 (2)C6B—C1B—C7B123.7 (11)
N2A—Cu1A—O4W97.5 (2)C1B—C2B—N8B117.3 (5)
N3A—Cu1A—N2A95.1 (2)C3B—C2B—C1B126.8 (6)
N3A—Cu1A—N4A85.2 (2)C3B—C2B—N8B115.8 (6)
N3A—Cu1A—O1W89.89 (19)C2B—C3B—H3B121.8
N3A—Cu1A—O4W87.80 (19)C2B—C3B—C4B116.5 (7)
N4A—Cu1A—N2A178.6 (3)C4B—C3B—H3B121.8
N4A—Cu1A—O1W95.3 (2)C3B—C4B—H4B120.5
N4A—Cu1A—O4W83.9 (2)C3B—C4B—C5B119.0 (8)
O4W—Cu1A—O1W177.6 (2)C5B—C4B—H4B120.5
Cu1A—N2A—H2AA110.2C4B—C5B—H5B118.9
Cu1A—N2A—H2AB110.2C6B—C5B—C4B122.1 (8)
H2AA—N2A—H2AB108.5C6B—C5B—H5B118.9
C12A—N2A—Cu1A107.4 (4)C1B—C6B—H6B119.5
C12A—N2A—H2AA110.2C5B—C6B—C1B120.9 (7)
C12A—N2A—H2AB110.2C5B—C6B—H6B119.5
Cu1A—N3A—H3AA110.0O71B—C7B—C1B118.3 (9)
Cu1A—N3A—H3AB110.0O71B—C7B—O72B124.7 (9)
H3AA—N3A—H3AB108.4O72B—C7B—C1B117.0 (9)
C13A—N3A—Cu1A108.3 (4)O81B—N8B—C2B119.5 (8)
C13A—N3A—H3AA110.0O81B—N8B—O82B121.7 (9)
C13A—N3A—H3AB110.0O82B—N8B—C2B118.8 (7)
Cu1A—N4A—H4AA110.0C2G—C1G—C7G120.1 (14)
Cu1A—N4A—H4AB110.0C6G—C1G—C2G122.7 (6)
H4AA—N4A—H4AB108.4C6G—C1G—C7G116.9 (15)
C14A—N4A—Cu1A108.4 (4)C1G—C2G—N8G122.9 (6)
C14A—N4A—H4AA110.0C3G—C2G—C1G115.8 (7)
C14A—N4A—H4AB110.0C3G—C2G—N8G121.2 (7)
N1A—C11A—H11A110.0C2G—C3G—H3G119.4
N1A—C11A—H11B110.0C2G—C3G—C4G121.2 (10)
N1A—C11A—C12A108.4 (6)C4G—C3G—H3G119.4
H11A—C11A—H11B108.4C3G—C4G—H4G118.5
C12A—C11A—H11A110.0C5G—C4G—C3G123.1 (11)
C12A—C11A—H11B110.0C5G—C4G—H4G118.5
N2A—C12A—C11A107.2 (5)C4G—C5G—H5G122.1
N2A—C12A—H12A110.3C4G—C5G—C6G115.8 (11)
N2A—C12A—H12B110.3C6G—C5G—H5G122.1
C11A—C12A—H12A110.3C1G—C6G—H6G119.4
C11A—C12A—H12B110.3C5G—C6G—C1G121.2 (10)
H12A—C12A—H12B108.5C5G—C6G—H6G119.4
N3A—C13A—H13A110.1O71G—C7G—C1G112.5 (12)
N3A—C13A—H13B110.1O71G—C7G—O72G128.1 (12)
N3A—C13A—C14A107.9 (6)O72G—C7G—C1G119.0 (13)
H13A—C13A—H13B108.4O81G—N8G—C2G117.8 (11)
C14A—C13A—H13A110.1O82G—N8G—C2G114.6 (10)
C14A—C13A—H13B110.1O82G—N8G—O81G126.9 (12)
N4A—C14A—C13A107.2 (5)C2A—C1A—C6A117.3 (6)
N4A—C14A—H14A110.3C2A—C1A—C7A125.6 (7)
N4A—C14A—H14B110.3C6A—C1A—C7A116.6 (8)
C13A—C14A—H14A110.3C1A—C2A—N8A118.5 (6)
C13A—C14A—H14B110.3C3A—C2A—C1A124.1 (7)
H14A—C14A—H14B108.5C3A—C2A—N8A117.0 (7)
C2D—C1D—C6D116.1 (7)C2A—C3A—H3A121.4
C2D—C1D—C7D128.2 (6)C2A—C3A—C4A117.3 (8)
C6D—C1D—C7D115.5 (6)C4A—C3A—H3A121.4
C1D—C2D—C3D123.4 (8)C3A—C4A—H4A119.6
C1D—C2D—N8D117.6 (7)C3A—C4A—C5A120.8 (8)
C3D—C2D—N8D118.8 (8)C5A—C4A—H4A119.6
C2D—C3D—H3D120.9C4A—C5A—H5A119.7
C4D—C3D—C2D118.2 (10)C6A—C5A—C4A120.6 (8)
C4D—C3D—H3D120.9C6A—C5A—H5A119.7
C3D—C4D—H4D119.6C1A—C6A—H6A120.1
C5D—C4D—C3D120.7 (9)C5A—C6A—C1A119.8 (8)
C5D—C4D—H4D119.6C5A—C6A—H6A120.1
C4D—C5D—H5D119.1O71A—C7A—C1A116.5 (8)
C4D—C5D—C6D121.8 (10)O71A—C7A—O72A125.7 (9)
C6D—C5D—H5D119.1O72A—C7A—C1A117.5 (9)
C1D—C6D—H6D120.2O81A—N8A—C2A119.9 (8)
C5D—C6D—C1D119.7 (9)O81A—N8A—O82A122.5 (8)
C5D—C6D—H6D120.2O82A—N8A—C2A117.6 (7)
O71D—C7D—C1D115.1 (10)C2F—C1F—C7F120.1 (10)
O72D—C7D—C1D118.9 (8)C6F—C1F—C2F115.7 (7)
O72D—C7D—O71D126.0 (11)C6F—C1F—C7F124.0 (11)
O81D—N8D—C2D118.2 (9)C1F—C2F—N8F119.8 (8)
O82D—N8D—C2D116.1 (8)C3F—C2F—C1F124.0 (9)
O82D—N8D—O81D125.6 (9)C3F—C2F—N8F116.1 (9)
C2E—C1E—C7E118.8 (7)C2F—C3F—H3F120.7
C6E—C1E—C2E113.1 (8)C2F—C3F—C4F118.5 (11)
C6E—C1E—C7E128.0 (8)C4F—C3F—H3F120.7
C1E—C2E—C3E123.3 (10)C3F—C4F—H4F120.5
C1E—C2E—N8E122.3 (9)C5F—C4F—C3F118.9 (11)
C3E—C2E—N8E114.2 (9)C5F—C4F—H4F120.5
C2E—C3E—H3E120.4C4F—C5F—H5F119.0
C4E—C3E—C2E119.3 (12)C4F—C5F—C6F122.0 (11)
C4E—C3E—H3E120.4C6F—C5F—H5F119.0
C3E—C4E—H4E120.6C1F—C6F—H6F119.6
C5E—C4E—C3E118.8 (11)C5F—C6F—C1F120.9 (11)
C5E—C4E—H4E120.6C5F—C6F—H6F119.6
C4E—C5E—H5E118.8O71F—C7F—C1F116.2 (11)
C4E—C5E—C6E122.4 (12)O71F—C7F—O72F126.6 (14)
C6E—C5E—H5E118.8O72F—C7F—C1F116.1 (12)
C1E—C6E—C5E123.2 (11)O81F—N8F—C2F121.7 (11)
C1E—C6E—H6E118.4O81F—N8F—O82F120.4 (11)
C5E—C6E—H6E118.4O82F—N8F—C2F117.8 (11)
O71E—C7E—C1E119.3 (12)C2C—C1C—C6C117.1 (5)
O72E—C7E—C1E112.8 (10)C2C—C1C—C7C124.6 (7)
O72E—C7E—O71E127.8 (15)C6C—C1C—C7C117.8 (7)
O81E—N8E—C2E118.5 (11)C1C—C2C—C3C123.4 (6)
O81E—N8E—O82E122.1 (12)C1C—C2C—N8C119.1 (5)
O82E—N8E—C2E119.4 (11)C3C—C2C—N8C117.3 (5)
H1BA—N1B—H1BB108.4C2C—C3C—H3C120.4
Cu1B—N1B—H1BA110.1C4C—C3C—C2C119.1 (6)
Cu1B—N1B—H1BB110.1C4C—C3C—H3C120.4
C11B—N1B—H1BA110.1C3C—C4C—H4C120.7
C11B—N1B—H1BB110.1C3C—C4C—C5C118.5 (6)
C11B—N1B—Cu1B108.1 (4)C5C—C4C—H4C120.7
N1B—Cu1B—N2B84.8 (2)C4C—C5C—H5C119.4
N1B—Cu1B—N3B179.5 (3)C6C—C5C—C4C121.1 (6)
N1B—Cu1B—N4B94.8 (2)C6C—C5C—H5C119.4
N1B—Cu1B—O2W90.9 (2)C1C—C6C—H6C119.7
N1B—Cu1B—O3W85.4 (2)C5C—C6C—C1C120.7 (6)
N2B—Cu1B—O2W94.9 (2)C5C—C6C—H6C119.7
N2B—Cu1B—O3W85.2 (2)O71C—C7C—C1C115.8 (7)
N3B—Cu1B—N2B95.4 (2)O72C—C7C—C1C116.8 (7)
N3B—Cu1B—N4B85.0 (2)O72C—C7C—O71C126.8 (7)
N3B—Cu1B—O2W89.6 (2)O81C—N8C—C2C116.2 (6)
N3B—Cu1B—O3W94.1 (2)O82C—N8C—C2C118.7 (6)
N4B—Cu1B—N2B179.3 (3)O82C—N8C—O81C125.0 (6)
N4B—Cu1B—O2W84.6 (2)C2H—C1H—C7H116 (2)
N4B—Cu1B—O3W95.3 (2)C6H—C1H—C2H121.2 (12)
O2W—Cu1B—O3W176.3 (2)C6H—C1H—C7H123 (2)
Cu1B—N2B—H2BA110.3C1H—C2H—N8H121.7 (14)
Cu1B—N2B—H2BB110.3C3H—C2H—C1H119.2 (14)
H2BA—N2B—H2BB108.5C3H—C2H—N8H119.1 (14)
C12B—N2B—Cu1B107.1 (4)C2H—C3H—H3H119.4
C12B—N2B—H2BA110.3C4H—C3H—C2H121.2 (18)
C12B—N2B—H2BB110.3C4H—C3H—H3H119.4
Cu1B—N3B—H3BA109.9C3H—C4H—H4H120.5
Cu1B—N3B—H3BB109.9C3H—C4H—C5H119.0 (18)
H3BA—N3B—H3BB108.3C5H—C4H—H4H120.5
C13B—N3B—Cu1B108.9 (4)C4H—C5H—H5H119.7
C13B—N3B—H3BA109.9C6H—C5H—C4H120.6 (19)
C13B—N3B—H3BB109.9C6H—C5H—H5H119.7
Cu1B—N4B—H4BA110.2C1H—C6H—C5H118.3 (17)
Cu1B—N4B—H4BB110.2C1H—C6H—H6H120.8
H4BA—N4B—H4BB108.5C5H—C6H—H6H120.8
C14B—N4B—Cu1B107.4 (4)O71H—C7H—C1H120 (2)
C14B—N4B—H4BA110.2O72H—C7H—C1H117.4 (19)
C14B—N4B—H4BB110.2O72H—C7H—O71H119 (3)
N1B—C11B—H11C110.1O81H—N8H—C2H119.9 (17)
N1B—C11B—H11D110.1O82H—N8H—C2H116.5 (17)
N1B—C11B—C12B108.0 (6)O82H—N8H—O81H123.5 (18)
H11C—C11B—H11D108.4Cu1A—O1W—H1WA124.2
C12B—C11B—H11C110.1Cu1A—O1W—H1WB101.4
C12B—C11B—H11D110.1H1WA—O1W—H1WB109.5
N2B—C12B—H12C110.1Cu1B—O2W—H2WA82.9
N2B—C12B—H12D110.1Cu1B—O2W—H2WB112.6
C11B—C12B—N2B107.9 (5)H2WA—O2W—H2WB90.8
C11B—C12B—H12C110.1Cu1B—O3W—H3WA125.0
C11B—C12B—H12D110.1Cu1B—O3W—H3WB106.4
H12C—C12B—H12D108.4H3WA—O3W—H3WB92.7
N3B—C13B—H13C110.3Cu1A—O4W—H4WA99.0
N3B—C13B—H13D110.3Cu1A—O4W—H4WB109.8
N3B—C13B—C14B106.9 (6)H4WA—O4W—H4WB109.5
N1A—C11A—C12A—N2A53.3 (7)C6G—C1G—C7G—O71G118 (3)
Cu1A—N1A—C11A—C12A39.2 (6)C6G—C1G—C7G—O72G56 (4)
Cu1A—N2A—C12A—C11A40.7 (6)C7G—C1G—C2G—C3G167.7 (17)
Cu1A—N3A—C13A—C14A39.2 (6)C7G—C1G—C2G—N8G14.9 (17)
Cu1A—N4A—C14A—C13A40.1 (6)C7G—C1G—C6G—C5G170.9 (19)
N3A—C13A—C14A—N4A52.8 (7)N8G—C2G—C3G—C4G173.8 (14)
C1D—C2D—C3D—C4D2 (2)C1A—C2A—C3A—C4A1.8 (19)
C1D—C2D—N8D—O81D31.0 (18)C1A—C2A—N8A—O81A150.2 (11)
C1D—C2D—N8D—O82D153.0 (12)C1A—C2A—N8A—O82A28.7 (16)
C2D—C1D—C6D—C5D2.9 (17)C2A—C1A—C6A—C5A1.4 (16)
C2D—C1D—C7D—O71D130.2 (19)C2A—C1A—C7A—O71A44 (2)
C2D—C1D—C7D—O72D47.0 (15)C2A—C1A—C7A—O72A130.7 (14)
C2D—C3D—C4D—C5D1.6 (19)C2A—C3A—C4A—C5A0.4 (16)
C3D—C2D—N8D—O81D143.0 (13)C3A—C2A—N8A—O81A36.2 (17)
C3D—C2D—N8D—O82D33.1 (18)C3A—C2A—N8A—O82A144.9 (11)
C3D—C4D—C5D—C6D2.4 (19)C3A—C4A—C5A—C6A1.5 (16)
C4D—C5D—C6D—C1D0.0 (19)C4A—C5A—C6A—C1A0.6 (17)
C6D—C1D—C2D—C3D4 (2)C6A—C1A—C2A—C3A2.7 (18)
C6D—C1D—C2D—N8D170.0 (12)C6A—C1A—C2A—N8A170.4 (10)
C6D—C1D—C7D—O71D55.8 (19)C6A—C1A—C7A—O71A127.6 (14)
C6D—C1D—C7D—O72D127.0 (11)C6A—C1A—C7A—O72A57.6 (18)
C7D—C1D—C2D—C3D170.2 (11)C7A—C1A—C2A—C3A168.9 (12)
C7D—C1D—C2D—N8D16.1 (19)C7A—C1A—C2A—N8A17.9 (18)
C7D—C1D—C6D—C5D171.8 (10)C7A—C1A—C6A—C5A171.0 (11)
N8D—C2D—C3D—C4D172.0 (12)N8A—C2A—C3A—C4A171.4 (10)
C1E—C2E—C3E—C4E2 (3)C1F—C2F—C3F—C4F1 (3)
C1E—C2E—N8E—O81E29 (3)C1F—C2F—N8F—O81F146.7 (16)
C1E—C2E—N8E—O82E149.5 (17)C1F—C2F—N8F—O82F29 (2)
C2E—C1E—C6E—C5E1 (2)C2F—C1F—C6F—C5F3 (2)
C2E—C1E—C7E—O71E127 (3)C2F—C1F—C7F—O71F58 (3)
C2E—C1E—C7E—O72E57.0 (16)C2F—C1F—C7F—O72F133 (2)
C2E—C3E—C4E—C5E1 (2)C2F—C3F—C4F—C5F1 (3)
C3E—C2E—N8E—O81E145.5 (16)C3F—C2F—N8F—O81F38 (2)
C3E—C2E—N8E—O82E36 (2)C3F—C2F—N8F—O82F145.7 (17)
C3E—C4E—C5E—C6E1 (2)C3F—C4F—C5F—C6F2 (3)
C4E—C5E—C6E—C1E1 (3)C4F—C5F—C6F—C1F3 (3)
C6E—C1E—C2E—C3E1 (2)C6F—C1F—C2F—C3F2 (3)
C6E—C1E—C2E—N8E172.6 (17)C6F—C1F—C2F—N8F172.5 (16)
C6E—C1E—C7E—O71E58 (3)C6F—C1F—C7F—O71F116 (2)
C6E—C1E—C7E—O72E118.5 (15)C6F—C1F—C7F—O72F52 (3)
C7E—C1E—C2E—C3E174.9 (15)C7F—C1F—C2F—C3F172.9 (18)
C7E—C1E—C2E—N8E11 (2)C7F—C1F—C2F—N8F13 (2)
C7E—C1E—C6E—C5E174.8 (12)C7F—C1F—C6F—C5F172.0 (16)
N8E—C2E—C3E—C4E172.7 (15)N8F—C2F—C3F—C4F173.4 (16)
N1B—C11B—C12B—N2B54.4 (7)C1C—C2C—C3C—C4C0.1 (12)
Cu1B—N1B—C11B—C12B43.4 (6)C1C—C2C—N8C—O81C36.2 (10)
Cu1B—N2B—C12B—C11B38.0 (6)C1C—C2C—N8C—O82C147.5 (7)
Cu1B—N3B—C13B—C14B39.8 (6)C2C—C1C—C6C—C5C0.5 (13)
Cu1B—N4B—C14B—C13B39.0 (7)C2C—C1C—C7C—O71C140.6 (11)
N3B—C13B—C14B—N4B52.7 (7)C2C—C1C—C7C—O72C48 (2)
C1B—C2B—C3B—C4B1.7 (14)C2C—C3C—C4C—C5C1.2 (11)
C1B—C2B—N8B—O81B36.9 (11)C3C—C2C—N8C—O81C139.0 (7)
C1B—C2B—N8B—O82B145.1 (8)C3C—C2C—N8C—O82C37.3 (11)
C2B—C1B—C6B—C5B2.6 (16)C3C—C4C—C5C—C6C1.7 (11)
C2B—C1B—C7B—O71B60 (3)C4C—C5C—C6C—C1C0.8 (14)
C2B—C1B—C7B—O72B120 (2)C6C—C1C—C2C—C3C1.0 (13)
C2B—C3B—C4B—C5B3.2 (15)C6C—C1C—C2C—N8C173.9 (8)
C3B—C2B—N8B—O81B140.4 (10)C6C—C1C—C7C—O71C47.3 (18)
C3B—C2B—N8B—O82B37.5 (12)C6C—C1C—C7C—O72C124.6 (13)
C3B—C4B—C5B—C6B1.9 (16)C7C—C1C—C2C—C3C171.2 (10)
C4B—C5B—C6B—C1B1.2 (19)C7C—C1C—C2C—N8C13.9 (14)
C6B—C1B—C2B—C3B1.2 (12)C7C—C1C—C6C—C5C172.3 (10)
C6B—C1B—C2B—N8B175.8 (9)N8C—C2C—C3C—C4C174.8 (7)
C6B—C1B—C7B—O71B116 (2)C1H—C2H—C3H—C4H9 (5)
C6B—C1B—C7B—O72B63 (3)C1H—C2H—N8H—O81H32 (4)
C7B—C1B—C2B—C3B175.6 (12)C1H—C2H—N8H—O82H150 (3)
C7B—C1B—C2B—N8B7.5 (13)C2H—C1H—C6H—C5H5 (5)
C7B—C1B—C6B—C5B174.1 (13)C2H—C1H—C7H—O71H120 (5)
N8B—C2B—C3B—C4B178.7 (9)C2H—C1H—C7H—O72H39 (6)
C1G—C2G—C3G—C4G3.7 (19)C2H—C3H—C4H—C5H5 (5)
C1G—C2G—N8G—O81G32.4 (17)C3H—C2H—N8H—O81H145 (3)
C1G—C2G—N8G—O82G156.9 (11)C3H—C2H—N8H—O82H32 (4)
C2G—C1G—C6G—C5G2 (3)C3H—C4H—C5H—C6H1 (5)
C2G—C1G—C7G—O71G56 (4)C4H—C5H—C6H—C1H1 (5)
C2G—C1G—C7G—O72G131 (3)C6H—C1H—C2H—C3H9 (4)
C2G—C3G—C4G—C5G1 (3)C6H—C1H—C2H—N8H169 (3)
C3G—C2G—N8G—O81G144.9 (14)C6H—C1H—C7H—O71H56 (7)
C3G—C2G—N8G—O82G25.7 (18)C6H—C1H—C7H—O72H145 (5)
C3G—C4G—C5G—C6G4 (2)C7H—C1H—C2H—C3H175 (3)
C4G—C5G—C6G—C1G2 (3)C7H—C1H—C2H—N8H7 (4)
C6G—C1G—C2G—C3G5.5 (16)C7H—C1H—C6H—C5H179 (4)
C6G—C1G—C2G—N8G172.0 (14)N8H—C2H—C3H—C4H169 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O71B0.911.982.881 (14)172
N3A—H3AB···O72D0.911.902.809 (11)174
N1B—H1BB···O72C0.911.992.902 (8)174
N1B—H1BB···O72H0.911.862.77 (2)172
N2B—H2BB···O72A0.912.022.874 (12)155
N3B—H3BA···O71A0.911.892.795 (10)176
N4B—H4BA···O71H0.911.932.79 (3)158
O1W—H1WA···O72A0.851.972.794 (13)164
O1W—H1WA···O72F0.851.922.719 (18)156
O1W—H1WB···O71D0.851.942.763 (19)162
O1W—H1WB···O71E0.851.872.69 (3)162
O2W—H2WA···O71C0.871.982.739 (9)145
O2W—H2WA···O71H0.872.032.78 (3)143
O2W—H2WB···O71Ci1.071.782.803 (10)160
O2W—H2WB···O71Hi1.071.782.76 (3)152
O3W—H3WA···O71Dii0.851.922.739 (15)160
O3W—H3WA···O71Eii0.851.992.808 (19)161
O3W—H3WB···O72A0.852.042.750 (13)141
O3W—H3WB···O72F0.852.042.774 (19)145
O4W—H4WA···O72B0.851.912.753 (12)173
O4W—H4WA···O72G0.851.822.662 (17)172
O4W—H4WB···O72Biii0.851.902.726 (13)164
O4W—H4WB···O72Giii0.851.992.829 (17)168
Symmetry codes: (i) x, y, z1/2; (ii) x, y, z+1; (iii) x, y+1, z1/2.
 

Acknowledgements

We would like to thank the EPSRC for an equipment grant, which funded the diffractometer at Heriot-Watt University.

References

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