# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MC136016YG22
_database_code_depnum_ccdc_archive 'CCDC 1515383'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H40 Cd2 Cl2 N10 O6'
_chemical_formula_moiety         'C28 H40 Cd2 Cl2 N10 O6'
_chemical_formula_weight         908.41
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.9906(5)
_cell_length_b                   12.1122(5)
_cell_length_c                   13.7302(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.889(7)
_cell_angle_gamma                90.0000
_cell_volume                     1826.78(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8405
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.00
_exptl_absorpt_coefficient_mu    1.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_T_max  0.872

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12504
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.364
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4161
_reflns_number_gt                2901
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0692
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0233P)²+2.7444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.81
_refine_diff_density_min         -1.01
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cd Cd -0.8075 1.2024
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.31794(3) 0.21428(3) 0.49440(2) 0.04291(11) Uani 1 1 d . . .
Cl1 Cl 0.10145(11) 0.16904(13) 0.49810(9) 0.0671(4) Uani 1 1 d . . .
O1 O 0.4679(3) -0.2070(2) 0.4596(2) 0.0473(7) Uani 1 1 d . . .
O2 O 0.5870(3) -0.0728(3) 0.4109(2) 0.0513(8) Uani 1 1 d . . .
O3 O 0.3025(3) 0.3270(3) 0.6316(2) 0.0545(8) Uani 1 1 d . . .
N1 N 0.3987(3) 0.0310(3) 0.3094(2) 0.0411(8) Uani 1 1 d . . .
N2 N 0.3791(3) 0.1338(3) 0.3465(2) 0.0381(8) Uani 1 1 d . . .
N3 N 0.3640(3) 0.3535(3) 0.3849(2) 0.0428(8) Uani 1 1 d . . .
N4 N 0.3613(3) 0.4659(3) 0.3810(2) 0.0422(8) Uani 1 1 d . . .
N11 N 0.2707(3) 0.3208(3) 0.7936(3) 0.0552(10) Uani 1 1 d . . .
C1 C 0.4846(4) -0.1184(3) 0.4160(3) 0.0385(9) Uani 1 1 d . . .
C2 C 0.3737(4) -0.0656(3) 0.3672(3) 0.0431(10) Uani 1 1 d . . .
H2A H 0.3335 -0.1200 0.3256 0.052 Uiso 1 1 calc R . .
H2B H 0.3175 -0.0451 0.4171 0.052 Uiso 1 1 calc R . .
C3 C 0.4778(5) -0.0636(4) 0.1640(4) 0.0676(15) Uani 1 1 d . . .
H3A H 0.4062 -0.1077 0.1526 0.081 Uiso 1 1 calc R . .
H3B H 0.5375 -0.1056 0.2006 0.081 Uiso 1 1 calc R . .
H3C H 0.5103 -0.0423 0.1027 0.081 Uiso 1 1 calc R . .
C4 C 0.4457(4) 0.0371(4) 0.2198(3) 0.0458(10) Uani 1 1 d . . .
C5 C 0.4559(4) 0.1470(4) 0.1974(3) 0.0440(10) Uani 1 1 d . . .
H5 H 0.4846 0.1773 0.1403 0.053 Uiso 1 1 calc R . .
C6 C 0.4140(4) 0.2040(4) 0.2783(3) 0.0394(9) Uani 1 1 d . . .
C7 C 0.4015(4) 0.3221(3) 0.2972(3) 0.0376(9) Uani 1 1 d . . .
C8 C 0.4229(4) 0.4138(3) 0.2385(3) 0.0429(10) Uani 1 1 d . . .
H8 H 0.4496 0.4136 0.1750 0.052 Uiso 1 1 calc R . .
C9 C 0.3964(4) 0.5038(3) 0.2941(3) 0.0406(10) Uani 1 1 d . . .
C10 C 0.4006(4) 0.6248(3) 0.2720(3) 0.0482(11) Uani 1 1 d . . .
H10A H 0.4110 0.6352 0.2034 0.058 Uiso 1 1 calc R . .
H10B H 0.4677 0.6579 0.3078 0.058 Uiso 1 1 calc R . .
H10C H 0.3260 0.6588 0.2905 0.058 Uiso 1 1 calc R . .
C11 C 0.3279(5) 0.5293(4) 0.4660(3) 0.0589(13) Uani 1 1 d . . .
H11A H 0.3794 0.5931 0.4723 0.071 Uiso 1 1 calc R . .
H11B H 0.3375 0.4843 0.5233 0.071 Uiso 1 1 calc R . .
H11C H 0.2445 0.5525 0.4585 0.071 Uiso 1 1 calc R . .
C12 C 0.2707(4) 0.2784(4) 0.7058(3) 0.0548(12) Uani 1 1 d . . .
H12 H 0.2446 0.2057 0.6987 0.066 Uiso 1 1 calc R . .
C13 C 0.3059(6) 0.4338(5) 0.8122(5) 0.0864(19) Uani 1 1 d . . .
H13A H 0.3348 0.4663 0.7534 0.104 Uiso 1 1 calc R . .
H13B H 0.3695 0.4357 0.8618 0.104 Uiso 1 1 calc R . .
H13C H 0.2370 0.4747 0.8337 0.104 Uiso 1 1 calc R . .
C14 C 0.2327(7) 0.2562(6) 0.8766(4) 0.105(2) Uani 1 1 d . . .
H14A H 0.2852 0.1933 0.8849 0.126 Uiso 1 1 calc R . .
H14B H 0.1504 0.2317 0.8654 0.126 Uiso 1 1 calc R . .
H14C H 0.2376 0.3009 0.9343 0.126 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r8 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r8'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r8'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N3 2.326(3) . ?
Cd1 O3 2.337(3) . ?
Cd1 N2 2.370(3) . ?
Cd1 O2 2.373(3) 3_656 ?
Cd1 O1 2.419(3) 3_656 ?
Cd1 Cl1 2.4438(13) . ?
Cd1 C1 2.720(4) 3_656 ?
O1 C1 1.245(5) . ?
O1 Cd1 2.419(3) 3_656 ?
O2 C1 1.258(5) . ?
O2 Cd1 2.373(3) 3_656 ?
O3 C12 1.238(5) . ?
N1 C4 1.352(5) . ?
N1 N2 1.365(4) . ?
N1 C2 1.445(5) . ?
N2 C6 1.331(5) . ?
N3 C7 1.341(5) . ?
N3 N4 1.363(4) . ?
N4 C9 1.347(5) . ?
N4 C11 1.454(5) . ?
N11 C12 1.310(5) . ?
N11 C13 1.444(7) . ?
N11 C14 1.456(7) . ?
C1 C2 1.513(6) . ?
C1 Cd1 2.720(4) 3_656 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.489(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.372(6) . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(6) . ?
C7 C8 1.397(5) . ?
C8 C9 1.368(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.497(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cd1 O3 96.91(11) . . ?
N3 Cd1 N2 70.76(11) . . ?
O3 Cd1 N2 163.98(11) . . ?
N3 Cd1 O2 140.96(11) . 3_656 ?
O3 Cd1 O2 91.31(11) . 3_656 ?
N2 Cd1 O2 92.31(11) . 3_656 ?
N3 Cd1 O1 87.99(11) . 3_656 ?
O3 Cd1 O1 84.66(11) . 3_656 ?
N2 Cd1 O1 84.71(11) . 3_656 ?
O2 Cd1 O1 54.78(10) 3_656 3_656 ?
N3 Cd1 Cl1 114.12(10) . . ?
O3 Cd1 Cl1 91.00(9) . . ?
N2 Cd1 Cl1 103.25(9) . . ?
O2 Cd1 Cl1 103.77(8) 3_656 . ?
O1 Cd1 Cl1 157.86(8) 3_656 . ?
N3 Cd1 C1 114.49(12) . 3_656 ?
O3 Cd1 C1 87.89(11) . 3_656 ?
N2 Cd1 C1 88.13(11) . 3_656 ?
O2 Cd1 C1 27.54(10) 3_656 3_656 ?
O1 Cd1 C1 27.24(10) 3_656 3_656 ?
Cl1 Cd1 C1 131.14(9) . 3_656 ?
C1 O1 Cd1 90.0(3) . 3_656 ?
C1 O2 Cd1 91.8(2) . 3_656 ?
C12 O3 Cd1 114.6(3) . . ?
C4 N1 N2 111.1(3) . . ?
C4 N1 C2 129.0(4) . . ?
N2 N1 C2 119.9(3) . . ?
C6 N2 N1 105.5(3) . . ?
C6 N2 Cd1 115.9(3) . . ?
N1 N2 Cd1 138.4(2) . . ?
C7 N3 N4 104.8(3) . . ?
C7 N3 Cd1 117.0(3) . . ?
N4 N3 Cd1 138.1(3) . . ?
C9 N4 N3 111.6(3) . . ?
C9 N4 C11 128.2(4) . . ?
N3 N4 C11 120.1(3) . . ?
C12 N11 C13 121.8(4) . . ?
C12 N11 C14 121.2(5) . . ?
C13 N11 C14 117.0(5) . . ?
O1 C1 O2 123.5(4) . . ?
O1 C1 C2 116.6(4) . . ?
O2 C1 C2 119.9(4) . . ?
O1 C1 Cd1 62.8(2) . 3_656 ?
O2 C1 Cd1 60.7(2) . 3_656 ?
C2 C1 Cd1 179.3(3) . 3_656 ?
N1 C2 C1 114.9(3) . . ?
N1 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 107.0(4) . . ?
N1 C4 C3 121.9(4) . . ?
C5 C4 C3 131.1(4) . . ?
C4 C5 C6 105.7(4) . . ?
C4 C5 H5 127.2 . . ?
C6 C5 H5 127.2 . . ?
N2 C6 C5 110.7(4) . . ?
N2 C6 C7 118.0(3) . . ?
C5 C6 C7 131.3(4) . . ?
N3 C7 C8 110.8(4) . . ?
N3 C7 C6 118.1(3) . . ?
C8 C7 C6 131.1(4) . . ?
C9 C8 C7 105.6(4) . . ?
C9 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
N4 C9 C8 107.2(4) . . ?
N4 C9 C10 121.7(4) . . ?
C8 C9 C10 131.2(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N11 125.4(5) . . ?
O3 C12 H12 117.3 . . ?
N11 C12 H12 117.3 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N11 C14 H14A 109.5 . . ?
N11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cd1 O3 C12 176.0(3) . . . . ?
N2 Cd1 O3 C12 -145.3(4) . . . . ?
O2 Cd1 O3 C12 -42.2(3) 3_656 . . . ?
O1 Cd1 O3 C12 -96.7(3) 3_656 . . . ?
Cl1 Cd1 O3 C12 61.6(3) . . . . ?
C1 Cd1 O3 C12 -69.5(3) 3_656 . . . ?
C4 N1 N2 C6 0.4(4) . . . . ?
C2 N1 N2 C6 177.9(4) . . . . ?
C4 N1 N2 Cd1 -173.9(3) . . . . ?
C2 N1 N2 Cd1 3.7(6) . . . . ?
N3 Cd1 N2 C6 3.1(3) . . . . ?
O3 Cd1 N2 C6 -38.0(6) . . . . ?
O2 Cd1 N2 C6 -140.9(3) 3_656 . . . ?
O1 Cd1 N2 C6 -86.6(3) 3_656 . . . ?
Cl1 Cd1 N2 C6 114.4(3) . . . . ?
C1 Cd1 N2 C6 -113.7(3) 3_656 . . . ?
N3 Cd1 N2 N1 177.0(4) . . . . ?
O3 Cd1 N2 N1 135.9(4) . . . . ?
O2 Cd1 N2 N1 33.0(4) 3_656 . . . ?
O1 Cd1 N2 N1 87.3(4) 3_656 . . . ?
Cl1 Cd1 N2 N1 -71.7(4) . . . . ?
C1 Cd1 N2 N1 60.2(4) 3_656 . . . ?
O3 Cd1 N3 C7 168.9(3) . . . . ?
N2 Cd1 N3 C7 -0.6(3) . . . . ?
O2 Cd1 N3 C7 68.1(4) 3_656 . . . ?
O1 Cd1 N3 C7 84.5(3) 3_656 . . . ?
Cl1 Cd1 N3 C7 -96.9(3) . . . . ?
C1 Cd1 N3 C7 78.0(3) 3_656 . . . ?
O3 Cd1 N3 N4 -13.6(4) . . . . ?
N2 Cd1 N3 N4 176.9(4) . . . . ?
O2 Cd1 N3 N4 -114.3(4) 3_656 . . . ?
O1 Cd1 N3 N4 -98.0(4) 3_656 . . . ?
Cl1 Cd1 N3 N4 80.6(4) . . . . ?
C1 Cd1 N3 N4 -104.4(4) 3_656 . . . ?
C7 N3 N4 C9 -0.3(5) . . . . ?
Cd1 N3 N4 C9 -178.0(3) . . . . ?
C7 N3 N4 C11 -178.0(4) . . . . ?
Cd1 N3 N4 C11 4.3(6) . . . . ?
Cd1 O1 C1 O2 0.7(4) 3_656 . . . ?
Cd1 O1 C1 C2 -179.5(3) 3_656 . . . ?
Cd1 O2 C1 O1 -0.7(4) 3_656 . . . ?
Cd1 O2 C1 C2 179.5(3) 3_656 . . . ?
C4 N1 C2 C1 76.4(5) . . . . ?
N2 N1 C2 C1 -100.7(4) . . . . ?
O1 C1 C2 N1 -174.1(3) . . . . ?
O2 C1 C2 N1 5.7(5) . . . . ?
Cd1 C1 C2 N1 149(23) 3_656 . . . ?
N2 N1 C4 C5 -0.6(5) . . . . ?
C2 N1 C4 C5 -177.9(4) . . . . ?
N2 N1 C4 C3 178.8(4) . . . . ?
C2 N1 C4 C3 1.5(7) . . . . ?
N1 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 C6 -178.7(5) . . . . ?
N1 N2 C6 C5 0.1(4) . . . . ?
Cd1 N2 C6 C5 175.8(3) . . . . ?
N1 N2 C6 C7 179.0(3) . . . . ?
Cd1 N2 C6 C7 -5.2(5) . . . . ?
C4 C5 C6 N2 -0.4(5) . . . . ?
C4 C5 C6 C7 -179.2(4) . . . . ?
N4 N3 C7 C8 0.3(5) . . . . ?
Cd1 N3 C7 C8 178.6(3) . . . . ?
N4 N3 C7 C6 179.9(3) . . . . ?
Cd1 N3 C7 C6 -1.8(5) . . . . ?
N2 C6 C7 N3 4.8(6) . . . . ?
C5 C6 C7 N3 -176.5(4) . . . . ?
N2 C6 C7 C8 -175.7(4) . . . . ?
C5 C6 C7 C8 3.0(8) . . . . ?
N3 C7 C8 C9 -0.2(5) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
N3 N4 C9 C8 0.1(5) . . . . ?
C11 N4 C9 C8 177.7(4) . . . . ?
N3 N4 C9 C10 179.8(4) . . . . ?
C11 N4 C9 C10 -2.6(7) . . . . ?
C7 C8 C9 N4 0.0(5) . . . . ?
C7 C8 C9 C10 -179.6(4) . . . . ?
Cd1 O3 C12 N11 170.9(4) . . . . ?
C13 N11 C12 O3 1.8(8) . . . . ?
C14 N11 C12 O3 -179.3(5) . . . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1515381'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H32 Co N6 O7'
_chemical_formula_moiety         'C20 H32 Co N6 O7'
_chemical_formula_weight         527.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,+Y,1/2-Z
5 -X,-Y,-Z
6 -1/2+X,-1/2+Y,-1/2-Z
7 -1/2-X,-1/2+Y,+Z
8 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.1068(6)
_cell_length_b                   9.9563(5)
_cell_length_c                   17.5608(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2641.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4159
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108.00
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_T_max  0.933

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            3024
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         3.375
_diffrn_reflns_theta_full        27.490
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3024
_reflns_number_gt                1373
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2958
_refine_ls_wR_factor_gt          0.2068
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1410P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Co Co 0.3494 0.9721
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.0000 1.0000 0.5000 0.0510(4) Uani 1 2 d S . .
O1 O 0.8867(3) 0.9542(5) 0.5598(2) 0.0685(12) Uani 1 1 d . . .
O2 O 0.7893(3) 0.7928(5) 0.5841(3) 0.0869(15) Uani 1 1 d . . .
O3 O 1.0000 0.7506(6) 0.2500 0.0719(18) Uani 1 2 d S . .
O4 O 0.9220(3) 1.0739(5) 0.4069(2) 0.0799(14) Uani 1 1 d . . .
O5 O 0.7844(4) 0.5401(7) 0.6624(3) 0.0934(18) Uani 1 1 d . . .
N1 N 0.9756(3) 0.8015(5) 0.4634(3) 0.0528(12) Uani 1 1 d . . .
N2 N 1.0066(3) 0.7068(5) 0.4157(2) 0.0523(12) Uani 1 1 d . . .
N3 N 0.8233(4) 1.2053(7) 0.3467(4) 0.099(2) Uani 1 1 d . . .
C1 C 0.8562(4) 0.8378(7) 0.5522(3) 0.0617(16) Uani 1 1 d . . .
C2 C 0.9059(4) 0.7484(6) 0.4984(3) 0.0524(14) Uani 1 1 d . . .
C3 C 0.8927(4) 0.6173(7) 0.4710(4) 0.0670(17) Uani 1 1 d . . .
H3 H 0.8484 0.5581 0.4861 0.080 Uiso 1 1 calc R . .
C4 C 0.9577(4) 0.5928(6) 0.4174(3) 0.0600(15) Uani 1 1 d . . .
C5 C 0.9752(5) 0.4753(7) 0.3667(5) 0.087(2) Uani 1 1 d . . .
H5A H 0.9252 0.4611 0.3340 0.105 Uiso 1 1 calc R . .
H5B H 0.9849 0.3967 0.3972 0.105 Uiso 1 1 calc R . .
H5C H 1.0269 0.4927 0.3364 0.105 Uiso 1 1 calc R . .
C6 C 1.0800(4) 0.7423(6) 0.3656(3) 0.0607(15) Uani 1 1 d . . .
H6A H 1.1063 0.6608 0.3454 0.073 Uiso 1 1 calc R . .
H6B H 1.1250 0.7891 0.3948 0.073 Uiso 1 1 calc R . .
C7 C 1.0509(4) 0.8289(7) 0.3014(3) 0.0699(18) Uani 1 1 d . . .
H7A H 1.0156 0.9029 0.3206 0.084 Uiso 1 1 calc R . .
H7B H 1.1021 0.8658 0.2754 0.084 Uiso 1 1 calc R . .
C8 C 0.8593(5) 1.1515(8) 0.4078(5) 0.085(2) Uani 1 1 d . . .
H8 H 0.8353 1.1740 0.4549 0.102 Uiso 1 1 calc R . .
C9 C 0.7495(5) 1.3004(15) 0.3489(7) 0.191(7) Uani 1 1 d . . .
H9A H 0.6950 1.2533 0.3401 0.229 Uiso 1 1 calc R . .
H9B H 0.7576 1.3672 0.3101 0.229 Uiso 1 1 calc R . .
H9C H 0.7476 1.3431 0.3979 0.229 Uiso 1 1 calc R . .
C10 C 0.8595(9) 1.1751(11) 0.2719(6) 0.177(6) Uani 1 1 d . . .
H10A H 0.8957 1.0961 0.2750 0.212 Uiso 1 1 calc R . .
H10B H 0.8946 1.2494 0.2547 0.212 Uiso 1 1 calc R . .
H10C H 0.8119 1.1598 0.2367 0.212 Uiso 1 1 calc R . .
H1 H 0.785(8) 0.632(16) 0.616(8) 0.25(6) Uiso 1 1 d . . .
H2 H 0.746(3) 0.513(5) 0.637(3) 0.037(16) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r8 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r8'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r8'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.059(4) . ?
Co1 O1 2.059(4) 5_776 ?
Co1 N1 2.110(5) 5_776 ?
Co1 N1 2.111(5) . ?
Co1 O4 2.145(4) 5_776 ?
Co1 O4 2.145(4) . ?
O1 C1 1.254(7) . ?
O2 C1 1.239(7) . ?
O3 C7 1.419(7) 4_755 ?
O3 C7 1.419(7) . ?
O4 C8 1.222(8) . ?
O5 H1 1.22(15) . ?
O5 H2 0.79(5) . ?
N1 C2 1.328(7) . ?
N1 N2 1.345(6) . ?
N2 C4 1.354(7) . ?
N2 C6 1.460(7) . ?
N3 C8 1.317(8) . ?
N3 C10 1.454(12) . ?
N3 C9 1.462(12) . ?
C1 C2 1.500(8) . ?
C2 C3 1.406(8) . ?
C3 C4 1.381(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.494(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.486(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 180.0 . 5_776 ?
O1 Co1 N1 101.38(18) . 5_776 ?
O1 Co1 N1 78.62(18) 5_776 5_776 ?
O1 Co1 N1 78.62(18) . . ?
O1 Co1 N1 101.38(18) 5_776 . ?
N1 Co1 N1 180.0 5_776 . ?
O1 Co1 O4 89.55(17) . 5_776 ?
O1 Co1 O4 90.45(17) 5_776 5_776 ?
N1 Co1 O4 89.62(18) 5_776 5_776 ?
N1 Co1 O4 90.38(18) . 5_776 ?
O1 Co1 O4 90.45(17) . . ?
O1 Co1 O4 89.55(17) 5_776 . ?
N1 Co1 O4 90.38(18) 5_776 . ?
N1 Co1 O4 89.62(18) . . ?
O4 Co1 O4 180.0(2) 5_776 . ?
C1 O1 Co1 117.1(4) . . ?
C7 O3 C7 113.4(7) 4_755 . ?
C8 O4 Co1 129.3(5) . . ?
H1 O5 H2 83(7) . . ?
C2 N1 N2 106.5(5) . . ?
C2 N1 Co1 111.7(4) . . ?
N2 N1 Co1 141.7(4) . . ?
N1 N2 C4 112.6(5) . . ?
N1 N2 C6 118.0(5) . . ?
C4 N2 C6 129.1(5) . . ?
C8 N3 C10 119.7(8) . . ?
C8 N3 C9 123.8(9) . . ?
C10 N3 C9 116.4(7) . . ?
O2 C1 O1 125.9(6) . . ?
O2 C1 C2 118.6(6) . . ?
O1 C1 C2 115.5(5) . . ?
N1 C2 C3 108.9(5) . . ?
N1 C2 C1 116.9(5) . . ?
C3 C2 C1 134.1(6) . . ?
C4 C3 C2 107.2(5) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
N2 C4 C3 104.8(5) . . ?
N2 C4 C5 123.1(6) . . ?
C3 C4 C5 132.0(6) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 111.9(5) . . ?
N2 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C6 108.9(5) . . ?
O3 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
O3 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O4 C8 N3 124.6(8) . . ?
O4 C8 H8 117.7 . . ?
N3 C8 H8 117.7 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Co1 O1 C1 163(18) 5_776 . . . ?
N1 Co1 O1 C1 -177.6(4) 5_776 . . . ?
N1 Co1 O1 C1 2.4(4) . . . . ?
O4 Co1 O1 C1 -88.0(5) 5_776 . . . ?
O4 Co1 O1 C1 92.0(5) . . . . ?
O1 Co1 O4 C8 48.3(6) . . . . ?
O1 Co1 O4 C8 -131.7(6) 5_776 . . . ?
N1 Co1 O4 C8 -53.1(6) 5_776 . . . ?
N1 Co1 O4 C8 126.9(6) . . . . ?
O4 Co1 O4 C8 -17(19) 5_776 . . . ?
O1 Co1 N1 C2 -2.9(3) . . . . ?
O1 Co1 N1 C2 177.1(3) 5_776 . . . ?
N1 Co1 N1 C2 17(3) 5_776 . . . ?
O4 Co1 N1 C2 86.6(4) 5_776 . . . ?
O4 Co1 N1 C2 -93.4(4) . . . . ?
O1 Co1 N1 N2 177.1(6) . . . . ?
O1 Co1 N1 N2 -2.9(6) 5_776 . . . ?
N1 Co1 N1 N2 -163(3) 5_776 . . . ?
O4 Co1 N1 N2 -93.5(5) 5_776 . . . ?
O4 Co1 N1 N2 86.5(5) . . . . ?
C2 N1 N2 C4 1.1(6) . . . . ?
Co1 N1 N2 C4 -178.8(4) . . . . ?
C2 N1 N2 C6 175.6(4) . . . . ?
Co1 N1 N2 C6 -4.4(8) . . . . ?
Co1 O1 C1 O2 179.5(5) . . . . ?
Co1 O1 C1 C2 -1.5(7) . . . . ?
N2 N1 C2 C3 -0.6(6) . . . . ?
Co1 N1 C2 C3 179.4(4) . . . . ?
N2 N1 C2 C1 -176.9(4) . . . . ?
Co1 N1 C2 C1 3.0(6) . . . . ?
O2 C1 C2 N1 177.9(5) . . . . ?
O1 C1 C2 N1 -1.1(8) . . . . ?
O2 C1 C2 C3 2.8(10) . . . . ?
O1 C1 C2 C3 -176.3(6) . . . . ?
N1 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 175.3(6) . . . . ?
N1 N2 C4 C3 -1.2(6) . . . . ?
C6 N2 C4 C3 -174.8(5) . . . . ?
N1 N2 C4 C5 176.5(6) . . . . ?
C6 N2 C4 C5 2.9(10) . . . . ?
C2 C3 C4 N2 0.8(6) . . . . ?
C2 C3 C4 C5 -176.7(7) . . . . ?
N1 N2 C6 C7 -74.9(6) . . . . ?
C4 N2 C6 C7 98.5(7) . . . . ?
C7 O3 C7 C6 163.6(5) 4_755 . . . ?
N2 C6 C7 O3 -71.3(6) . . . . ?
Co1 O4 C8 N3 170.2(5) . . . . ?
C10 N3 C8 O4 -1.2(13) . . . . ?
C9 N3 C8 O4 -178.5(9) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H1 O2 . . . 2.868(8) 1.22(15) 1.70(16) 158(11) no
O5 H2 O2 . . 7_755 3.031(8) 0.79(5) 2.44(5) 134(5) no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1515379'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H18 Cu N4 O7'
_chemical_formula_moiety         'C12 H18 Cu N4 O7'
_chemical_formula_weight         393.84
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.9476
_cell_length_b                   9.25990(10)
_cell_length_c                   10.2507(2)
_cell_angle_alpha                88.279(5)
_cell_angle_beta                 74.957(5)
_cell_angle_gamma                72.294(4)
_cell_volume                     780.25(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3572
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             406.00
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7983
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3400
_reflns_number_gt                3242
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1148
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3400
_refine_ls_number_parameters     249
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0579P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.97
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.14128(3) 0.40784(3) 0.20668(3) 0.02971(13) Uani 1 1 d . . .
O1 O -0.3097(2) 0.5828(2) 0.31971(19) 0.0375(4) Uani 1 1 d . . .
O2 O -0.3401(2) 0.7789(2) 0.4570(2) 0.0405(4) Uani 1 1 d . . .
O3 O -0.2892(2) 0.3538(2) 0.11863(19) 0.0365(4) Uani 1 1 d . . .
O4 O -0.2892(2) 0.2069(2) -0.0503(2) 0.0427(4) Uani 1 1 d . . .
O5 O -0.1189(3) 0.2057(2) 0.3301(2) 0.0437(4) Uani 1 1 d . . .
O6 O -0.3292(2) 0.0741(3) 0.5041(2) 0.0409(4) Uani 1 1 d . . .
O7 O 0.1777(3) -0.0076(3) 0.2764(3) 0.0523(5) Uani 1 1 d . . .
N1 N 0.0017(2) 0.4873(2) 0.2789(2) 0.0300(4) Uani 1 1 d . . .
N2 N 0.1626(2) 0.4580(2) 0.2654(2) 0.0295(4) Uani 1 1 d . . .
N3 N 0.0245(2) 0.2996(2) 0.0430(2) 0.0302(4) Uani 1 1 d . . .
N4 N 0.1893(2) 0.2434(2) -0.00265(19) 0.0297(4) Uani 1 1 d . . .
C1 C -0.2556(3) 0.6647(3) 0.3819(2) 0.0303(5) Uani 1 1 d . . .
C2 C -0.0744(3) 0.6138(2) 0.3577(2) 0.0280(4) Uani 1 1 d . . .
C3 C 0.0367(3) 0.6675(3) 0.3972(3) 0.0323(5) Uani 1 1 d . . .
C4 C 0.1883(3) 0.5664(3) 0.3371(2) 0.0318(5) Uani 1 1 d . . .
C5 C 0.3539(3) 0.5658(3) 0.3406(3) 0.0434(6) Uani 1 1 d . . .
H5A H 0.4091 0.4707 0.3717 0.052 Uiso 1 1 calc R . .
H5B H 0.3450 0.6472 0.4009 0.052 Uiso 1 1 calc R . .
H5C H 0.4144 0.5792 0.2513 0.052 Uiso 1 1 calc R . .
C6 C 0.2807(3) 0.3202(3) 0.1917(3) 0.0335(5) Uani 1 1 d . . .
H6A H 0.2498 0.2330 0.2298 0.040 Uiso 1 1 calc R . .
H6B H 0.3864 0.3113 0.2052 0.040 Uiso 1 1 calc R . .
C7 C 0.2954(3) 0.3156(3) 0.0399(3) 0.0354(5) Uani 1 1 d . . .
H7A H 0.2717 0.4188 0.0108 0.042 Uiso 1 1 calc R . .
H7B H 0.4073 0.2619 -0.0068 0.042 Uiso 1 1 calc R . .
C8 C -0.2189(3) 0.2607(3) 0.0148(2) 0.0313(5) Uani 1 1 d . . .
C9 C -0.0363(3) 0.2213(3) -0.0264(2) 0.0292(4) Uani 1 1 d . . .
C10 C 0.0892(3) 0.1161(3) -0.1183(2) 0.0336(5) Uani 1 1 d . . .
C11 C 0.2318(3) 0.1316(3) -0.1014(2) 0.0319(5) Uani 1 1 d . . .
C12 C 0.4048(3) 0.0494(3) -0.1707(3) 0.0445(6) Uani 1 1 d . . .
H12A H 0.4642 0.0144 -0.1042 0.053 Uiso 1 1 calc R . .
H12B H 0.4519 0.1168 -0.2280 0.053 Uiso 1 1 calc R . .
H12C H 0.4097 -0.0358 -0.2244 0.053 Uiso 1 1 calc R . .
H1 H 0.020(4) 0.752(4) 0.449(3) 0.040(8) Uiso 1 1 d . . .
H2 H 0.071(4) 0.053(4) -0.177(3) 0.051(9) Uiso 1 1 d . . .
H3 H 0.206(5) -0.081(5) 0.208(5) 0.074(13) Uiso 1 1 d . . .
H4 H 0.215(6) -0.050(5) 0.330(4) 0.070(13) Uiso 1 1 d . . .
H6 H -0.035(5) 0.152(4) 0.319(4) 0.053(10) Uiso 1 1 d . . .
H7 H -0.192(5) 0.170(4) 0.379(4) 0.050(9) Uiso 1 1 d . . .
H8 H -0.325(4) -0.006(4) 0.491(3) 0.036(8) Uiso 1 1 d . . .
H9 H -0.440(6) 0.131(5) 0.509(5) 0.085(13) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r8 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r8'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r8'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9553(19) . ?
Cu1 O3 1.9662(17) . ?
Cu1 N3 1.981(2) . ?
Cu1 O1 1.9901(18) . ?
Cu1 O5 2.2154(19) . ?
O1 C1 1.276(3) . ?
O2 C1 1.242(3) . ?
O3 C8 1.284(3) . ?
O4 C8 1.233(3) . ?
O5 H6 0.75(4) . ?
O5 H7 0.85(4) . ?
O6 H8 0.74(3) . ?
O6 H9 0.96(5) . ?
O7 H3 0.92(5) . ?
O7 H4 0.76(4) . ?
N1 C2 1.332(3) . ?
N1 N2 1.352(3) . ?
N2 C4 1.369(3) . ?
N2 C6 1.462(3) . ?
N3 C9 1.341(3) . ?
N3 N4 1.362(3) . ?
N4 C11 1.365(3) . ?
N4 C7 1.468(3) . ?
C1 C2 1.499(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.387(3) . ?
C3 H1 0.91(3) . ?
C4 C5 1.490(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.528(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.506(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.381(3) . ?
C10 H2 0.92(4) . ?
C11 C12 1.492(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O3 171.79(8) . . ?
N1 Cu1 N3 97.00(8) . . ?
O3 Cu1 N3 82.44(8) . . ?
N1 Cu1 O1 81.55(7) . . ?
O3 Cu1 O1 95.74(7) . . ?
N3 Cu1 O1 156.94(9) . . ?
N1 Cu1 O5 95.61(8) . . ?
O3 Cu1 O5 92.59(8) . . ?
N3 Cu1 O5 95.22(8) . . ?
O1 Cu1 O5 107.84(8) . . ?
C1 O1 Cu1 115.23(14) . . ?
C8 O3 Cu1 115.03(15) . . ?
Cu1 O5 H6 115(3) . . ?
Cu1 O5 H7 131(2) . . ?
H6 O5 H7 113(4) . . ?
H8 O6 H9 104(4) . . ?
H3 O7 H4 104(4) . . ?
C2 N1 N2 107.00(18) . . ?
C2 N1 Cu1 114.34(15) . . ?
N2 N1 Cu1 138.44(16) . . ?
N1 N2 C4 110.00(19) . . ?
N1 N2 C6 120.98(19) . . ?
C4 N2 C6 128.83(19) . . ?
C9 N3 N4 106.42(19) . . ?
C9 N3 Cu1 111.49(15) . . ?
N4 N3 Cu1 138.73(16) . . ?
N3 N4 C11 110.29(19) . . ?
N3 N4 C7 121.11(19) . . ?
C11 N4 C7 128.0(2) . . ?
O2 C1 O1 125.4(2) . . ?
O2 C1 C2 120.0(2) . . ?
O1 C1 C2 114.6(2) . . ?
N1 C2 C3 110.5(2) . . ?
N1 C2 C1 114.2(2) . . ?
C3 C2 C1 135.3(2) . . ?
C2 C3 C4 105.7(2) . . ?
C2 C3 H1 129.6(19) . . ?
C4 C3 H1 124.6(19) . . ?
N2 C4 C3 106.8(2) . . ?
N2 C4 C5 122.6(2) . . ?
C3 C4 C5 130.6(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 114.11(19) . . ?
N2 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N4 C7 C6 115.5(2) . . ?
N4 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N4 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
O4 C8 O3 125.2(2) . . ?
O4 C8 C9 120.5(2) . . ?
O3 C8 C9 114.3(2) . . ?
N3 C9 C10 110.2(2) . . ?
N3 C9 C8 114.8(2) . . ?
C10 C9 C8 134.9(2) . . ?
C11 C10 C9 106.0(2) . . ?
C11 C10 H2 131(2) . . ?
C9 C10 H2 123(2) . . ?
N4 C11 C10 107.0(2) . . ?
N4 C11 C12 122.3(2) . . ?
C10 C11 C12 130.7(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O1 C1 1.27(17) . . . . ?
O3 Cu1 O1 C1 -170.91(17) . . . . ?
N3 Cu1 O1 C1 -86.7(2) . . . . ?
O5 Cu1 O1 C1 94.49(18) . . . . ?
N1 Cu1 O3 C8 96.3(5) . . . . ?
N3 Cu1 O3 C8 9.70(16) . . . . ?
O1 Cu1 O3 C8 166.56(17) . . . . ?
O5 Cu1 O3 C8 -85.22(17) . . . . ?
O3 Cu1 N1 C2 68.6(6) . . . . ?
N3 Cu1 N1 C2 154.11(17) . . . . ?
O1 Cu1 N1 C2 -2.67(16) . . . . ?
O5 Cu1 N1 C2 -109.92(17) . . . . ?
O3 Cu1 N1 N2 -105.2(5) . . . . ?
N3 Cu1 N1 N2 -19.7(2) . . . . ?
O1 Cu1 N1 N2 -176.4(2) . . . . ?
O5 Cu1 N1 N2 76.3(2) . . . . ?
C2 N1 N2 C4 0.4(3) . . . . ?
Cu1 N1 N2 C4 174.49(18) . . . . ?
C2 N1 N2 C6 175.9(2) . . . . ?
Cu1 N1 N2 C6 -10.1(4) . . . . ?
N1 Cu1 N3 C9 175.68(15) . . . . ?
O3 Cu1 N3 C9 -12.58(15) . . . . ?
O1 Cu1 N3 C9 -99.5(2) . . . . ?
O5 Cu1 N3 C9 79.35(16) . . . . ?
N1 Cu1 N3 N4 20.3(2) . . . . ?
O3 Cu1 N3 N4 -168.0(2) . . . . ?
O1 Cu1 N3 N4 105.1(3) . . . . ?
O5 Cu1 N3 N4 -76.0(2) . . . . ?
C9 N3 N4 C11 0.7(2) . . . . ?
Cu1 N3 N4 C11 156.89(19) . . . . ?
C9 N3 N4 C7 172.5(2) . . . . ?
Cu1 N3 N4 C7 -31.3(3) . . . . ?
Cu1 O1 C1 O2 179.8(2) . . . . ?
Cu1 O1 C1 C2 0.2(3) . . . . ?
N2 N1 C2 C3 -0.5(3) . . . . ?
Cu1 N1 C2 C3 -176.15(15) . . . . ?
N2 N1 C2 C1 179.16(18) . . . . ?
Cu1 N1 C2 C1 3.5(2) . . . . ?
O2 C1 C2 N1 177.9(2) . . . . ?
O1 C1 C2 N1 -2.5(3) . . . . ?
O2 C1 C2 C3 -2.6(4) . . . . ?
O1 C1 C2 C3 177.1(2) . . . . ?
N1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
N1 N2 C4 C3 -0.2(3) . . . . ?
C6 N2 C4 C3 -175.2(2) . . . . ?
N1 N2 C4 C5 -179.3(2) . . . . ?
C6 N2 C4 C5 5.8(4) . . . . ?
C2 C3 C4 N2 -0.1(3) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
N1 N2 C6 C7 67.4(3) . . . . ?
C4 N2 C6 C7 -118.1(3) . . . . ?
N3 N4 C7 C6 60.9(3) . . . . ?
C11 N4 C7 C6 -128.9(2) . . . . ?
N2 C6 C7 N4 -91.7(2) . . . . ?
Cu1 O3 C8 O4 176.1(2) . . . . ?
Cu1 O3 C8 C9 -4.9(2) . . . . ?
N4 N3 C9 C10 -0.9(2) . . . . ?
Cu1 N3 C9 C10 -164.23(15) . . . . ?
N4 N3 C9 C8 176.79(17) . . . . ?
Cu1 N3 C9 C8 13.4(2) . . . . ?
O4 C8 C9 N3 173.0(2) . . . . ?
O3 C8 C9 N3 -6.0(3) . . . . ?
O4 C8 C9 C10 -10.1(4) . . . . ?
O3 C8 C9 C10 171.0(2) . . . . ?
N3 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C11 -176.3(2) . . . . ?
N3 N4 C11 C10 -0.3(3) . . . . ?
C7 N4 C11 C10 -171.4(2) . . . . ?
N3 N4 C11 C12 179.8(2) . . . . ?
C7 N4 C11 C12 8.7(4) . . . . ?
C9 C10 C11 N4 -0.2(3) . . . . ?
C9 C10 C11 C12 179.6(2) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H6 O7 . . . 2.714(3) 0.75(4) 1.97(4) 173(5) no
O5 H7 O6 . . . 2.780(3) 0.86(4) 1.93(4) 171(4) no
O6 H8 O2 . . 1_545 2.825(3) 0.74(4) 2.09(4) 174(3) no
O6 H9 O2 . . 2_466 2.782(3) 0.96(5) 1.83(5) 171(4) no
O7 H3 O4 . . 2_555 2.776(3) 0.92(5) 1.87(4) 168(5) no
O7 H4 O6 . . 2_556 2.876(4) 0.76(5) 2.17(5) 155(5) no
_vrf_PLAT029_MC136001YG          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.949 Note
RESPONSE: The crystal was very tiny plate and weakly diffracting. We could not grow better 
quality crystal than this, evenafter many trials. 
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1515380'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H34 Co N6 O10'
_chemical_formula_moiety         'C20 H34 Co N6 O10'
_chemical_formula_weight         577.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.7238(9)
_cell_length_b                   8.9070(8)
_cell_length_c                   9.5349(9)
_cell_angle_alpha                92.976(7)
_cell_angle_beta                 106.274(8)
_cell_angle_gamma                111.903(8)
_cell_volume                     649.61(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5093
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             303.00
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_T_max  0.944

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10348
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2976
_reflns_number_gt                1696
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2505
_refine_ls_wR_factor_gt          0.1787
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     177
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0949P)²+1.7202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.88
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Co Co 0.3494 0.9721
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 1.0000 0.0375(4) Uani 1 2 d S . .
O1 O 0.2732(5) 0.3295(5) 0.8481(5) 0.0433(10) Uani 1 1 d . . .
O2 O 0.1511(6) 0.0818(6) 0.7052(5) 0.0603(13) Uani 1 1 d . . .
O3 O 0.5867(6) 0.5906(5) 0.8229(5) 0.0473(11) Uani 1 1 d . . .
O4 O 0.070(3) 0.501(4) 0.508(3) 0.294(9) Uani 1 1 d . . .
O5 O 0.1085(9) -0.1685(9) 0.4847(11) 0.090(2) Uani 1 1 d . . .
N1 N 0.5705(6) 0.2985(6) 0.9656(5) 0.0348(11) Uani 1 1 d . . .
N2 N 0.7106(6) 0.2581(6) 0.9997(5) 0.0374(11) Uani 1 1 d . . .
N3 N 0.5644(7) 0.6955(7) 0.6090(6) 0.0484(13) Uani 1 1 d . . .
C1 C 0.2766(8) 0.1956(8) 0.7974(7) 0.0416(14) Uani 1 1 d . . .
C2 C 0.4472(7) 0.1797(7) 0.8599(6) 0.0355(13) Uani 1 1 d . . .
C3 C 0.5047(8) 0.0620(7) 0.8250(7) 0.0437(15) Uani 1 1 d . . .
H3 H 0.4410 -0.0336 0.7543 0.052 Uiso 1 1 calc R . .
C4 C 0.6734(8) 0.1143(7) 0.9148(7) 0.0414(14) Uani 1 1 d . . .
C5 C 0.8067(9) 0.0423(9) 0.9319(9) 0.063(2) Uani 1 1 d . . .
H5A H 0.8800 0.0899 0.8734 0.075 Uiso 1 1 calc R . .
H5B H 0.7486 -0.0745 0.8988 0.075 Uiso 1 1 calc R . .
H5C H 0.8769 0.0654 1.0343 0.075 Uiso 1 1 calc R . .
C6 C 0.8714(7) 0.3677(8) 1.1162(7) 0.0451(15) Uani 1 1 d . . .
H6A H 0.9063 0.3047 1.1891 0.054 Uiso 1 1 calc R . .
H6B H 0.8483 0.4508 1.1659 0.054 Uiso 1 1 calc R . .
C7 C 1.0213(9) 0.4523(9) 1.0569(9) 0.062(2) Uani 1 1 d . . .
H7A H 1.1226 0.5249 1.1385 0.074 Uiso 1 1 calc R . .
H7B H 1.0516 0.3698 1.0153 0.074 Uiso 1 1 calc R . .
C8 C 0.5011(8) 0.6274(7) 0.7124(7) 0.0417(14) Uani 1 1 d . . .
H8 H 0.3852 0.6057 0.7016 0.050 Uiso 1 1 calc R . .
C9 C 0.7432(10) 0.7265(10) 0.6184(9) 0.064(2) Uani 1 1 d . . .
H9A H 0.7993 0.8351 0.5996 0.077 Uiso 1 1 calc R . .
H9B H 0.7429 0.6473 0.5460 0.077 Uiso 1 1 calc R . .
H9C H 0.8053 0.7174 0.7158 0.077 Uiso 1 1 calc R . .
C10 C 0.4595(12) 0.7395(11) 0.4854(9) 0.075(2) Uani 1 1 d . . .
H10A H 0.5244 0.8496 0.4745 0.090 Uiso 1 1 calc R . .
H10B H 0.3547 0.7333 0.5035 0.090 Uiso 1 1 calc R . .
H10C H 0.4298 0.6649 0.3962 0.090 Uiso 1 1 calc R . .
H2 H 0.013(11) -0.160(9) 0.413(9) 0.07(2) Uiso 1 1 d . . .
H4 H 0.067(10) -0.196(10) 0.554(8) 0.05(3) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r8 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r8'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r8'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.060(4) . ?
Co1 O1 2.060(4) 2_667 ?
Co1 O3 2.116(4) . ?
Co1 O3 2.116(4) 2_667 ?
Co1 N1 2.141(5) 2_667 ?
Co1 N1 2.141(5) . ?
O1 C1 1.278(7) . ?
O2 C1 1.240(7) . ?
O3 C8 1.246(7) . ?
O4 O4 1.18(3) 2_566 ?
O5 H2 0.95(8) . ?
O5 H4 0.84(7) . ?
N1 C2 1.314(7) . ?
N1 N2 1.359(6) . ?
N2 C4 1.355(8) . ?
N2 C6 1.465(7) . ?
N3 C8 1.327(8) . ?
N3 C10 1.446(9) . ?
N3 C9 1.454(9) . ?
C1 C2 1.503(8) . ?
C2 C3 1.382(8) . ?
C3 C4 1.363(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.501(8) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.524(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.463(14) 2_767 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 179.998(1) . 2_667 ?
O1 Co1 O3 89.41(17) . . ?
O1 Co1 O3 90.59(17) 2_667 . ?
O1 Co1 O3 90.59(17) . 2_667 ?
O1 Co1 O3 89.41(17) 2_667 2_667 ?
O3 Co1 O3 179.999(2) . 2_667 ?
O1 Co1 N1 101.97(17) . 2_667 ?
O1 Co1 N1 78.03(17) 2_667 2_667 ?
O3 Co1 N1 91.37(17) . 2_667 ?
O3 Co1 N1 88.63(17) 2_667 2_667 ?
O1 Co1 N1 78.03(17) . . ?
O1 Co1 N1 101.97(17) 2_667 . ?
O3 Co1 N1 88.63(17) . . ?
O3 Co1 N1 91.37(17) 2_667 . ?
N1 Co1 N1 180.000(2) 2_667 . ?
C1 O1 Co1 117.3(4) . . ?
C8 O3 Co1 126.2(4) . . ?
H2 O5 H4 101(7) . . ?
C2 N1 N2 105.6(5) . . ?
C2 N1 Co1 112.0(4) . . ?
N2 N1 Co1 141.4(4) . . ?
C4 N2 N1 110.8(5) . . ?
C4 N2 C6 130.3(5) . . ?
N1 N2 C6 118.9(5) . . ?
C8 N3 C10 121.6(6) . . ?
C8 N3 C9 119.8(6) . . ?
C10 N3 C9 118.6(6) . . ?
O2 C1 O1 124.8(6) . . ?
O2 C1 C2 119.9(6) . . ?
O1 C1 C2 115.2(5) . . ?
N1 C2 C3 111.0(5) . . ?
N1 C2 C1 117.0(5) . . ?
C3 C2 C1 132.0(6) . . ?
C4 C3 C2 106.2(5) . . ?
C4 C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
N2 C4 C3 106.3(5) . . ?
N2 C4 C5 121.2(6) . . ?
C3 C4 C5 132.5(6) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 113.0(5) . . ?
N2 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C7 C6 112.8(7) 2_767 . ?
C7 C7 H7A 109.0 2_767 . ?
C6 C7 H7A 109.0 . . ?
C7 C7 H7B 109.0 2_767 . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 N3 124.4(6) . . ?
O3 C8 H8 117.8 . . ?
N3 C8 H8 117.8 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Co1 O1 C1 -153(10) 2_667 . . . ?
O3 Co1 O1 C1 84.6(4) . . . . ?
O3 Co1 O1 C1 -95.4(4) 2_667 . . . ?
N1 Co1 O1 C1 175.9(4) 2_667 . . . ?
N1 Co1 O1 C1 -4.1(4) . . . . ?
O1 Co1 O3 C8 48.9(5) . . . . ?
O1 Co1 O3 C8 -131.1(5) 2_667 . . . ?
O3 Co1 O3 C8 111(16) 2_667 . . . ?
N1 Co1 O3 C8 -53.1(5) 2_667 . . . ?
N1 Co1 O3 C8 126.9(5) . . . . ?
O1 Co1 N1 C2 6.1(4) . . . . ?
O1 Co1 N1 C2 -173.9(4) 2_667 . . . ?
O3 Co1 N1 C2 -83.6(4) . . . . ?
O3 Co1 N1 C2 96.4(4) 2_667 . . . ?
N1 Co1 N1 C2 -55(53) 2_667 . . . ?
O1 Co1 N1 N2 172.4(6) . . . . ?
O1 Co1 N1 N2 -7.6(6) 2_667 . . . ?
O3 Co1 N1 N2 82.7(6) . . . . ?
O3 Co1 N1 N2 -97.3(6) 2_667 . . . ?
N1 Co1 N1 N2 111(53) 2_667 . . . ?
C2 N1 N2 C4 0.0(6) . . . . ?
Co1 N1 N2 C4 -166.8(5) . . . . ?
C2 N1 N2 C6 -179.7(5) . . . . ?
Co1 N1 N2 C6 13.4(8) . . . . ?
Co1 O1 C1 O2 -179.7(5) . . . . ?
Co1 O1 C1 C2 1.6(7) . . . . ?
N2 N1 C2 C3 0.2(6) . . . . ?
Co1 N1 C2 C3 171.4(4) . . . . ?
N2 N1 C2 C1 -178.4(4) . . . . ?
Co1 N1 C2 C1 -7.2(6) . . . . ?
O2 C1 C2 N1 -174.7(5) . . . . ?
O1 C1 C2 N1 4.1(8) . . . . ?
O2 C1 C2 C3 7.1(10) . . . . ?
O1 C1 C2 C3 -174.2(6) . . . . ?
N1 C2 C3 C4 -0.4(7) . . . . ?
C1 C2 C3 C4 177.9(6) . . . . ?
N1 N2 C4 C3 -0.3(6) . . . . ?
C6 N2 C4 C3 179.4(5) . . . . ?
N1 N2 C4 C5 -179.6(6) . . . . ?
C6 N2 C4 C5 0.1(10) . . . . ?
C2 C3 C4 N2 0.4(6) . . . . ?
C2 C3 C4 C5 179.6(7) . . . . ?
C4 N2 C6 C7 68.0(8) . . . . ?
N1 N2 C6 C7 -112.4(6) . . . . ?
N2 C6 C7 C7 57.3(11) . . . 2_767 ?
Co1 O3 C8 N3 174.7(4) . . . . ?
C10 N3 C8 O3 -178.2(6) . . . . ?
C9 N3 C8 O3 2.1(10) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H2 O2 . . 2_556 2.856(10) 0.95(9) 1.93(9) 165(7) no
O5 H4 O2 . . . 2.826(11) 0.84(9) 2.53(8) 102(6) no
O5 H4 O4 . . 2_556 2.80(3) 0.84(9) 2.49(8) 103(6) no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1515382'
_audit_update_record             
;
2016-11-06 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H44 Cu2 N12 O14'
_chemical_formula_moiety         'C28 H44 Cu2 N12 O14'
_chemical_formula_weight         899.82
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.7066(5)
_cell_length_b                   11.8913(3)
_cell_length_c                   19.4436(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.498(8)
_cell_angle_gamma                90.0000
_cell_volume                     3809.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17157
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1864.00
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.931

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            29927
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8687
_reflns_number_gt                5203
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1268
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8687
_refine_ls_number_parameters     521
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0961P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.78
_refine_diff_density_min         -1.10
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57525(3) 0.71642(4) 1.09006(3) 0.03007(15) Uani 1 1 d . . .
Cu2 Cu 0.90439(3) 0.21142(4) 0.91958(3) 0.03177(16) Uani 1 1 d . . .
O1 O 0.51016(17) 0.6906(2) 0.98369(16) 0.0344(6) Uani 1 1 d . . .
O2 O 0.59635(17) 0.5464(2) 1.01096(16) 0.0387(7) Uani 1 1 d . . .
O3 O 0.6517(2) 0.7064(3) 1.19403(19) 0.0430(8) Uani 1 1 d . . .
O4 O 0.65720(18) 0.7984(2) 1.06391(18) 0.0439(7) Uani 1 1 d . . .
O5 O 1.00179(19) -0.1948(2) 0.98125(17) 0.0428(7) Uani 1 1 d . . .
O6 O 1.08562(18) -0.0531(2) 0.99104(17) 0.0444(7) Uani 1 1 d . . .
O7 O 0.7970(2) 0.1696(3) 0.8388(2) 0.0448(8) Uani 1 1 d . . .
O8 O 0.84355(18) 0.2975(2) 0.96871(17) 0.0406(7) Uani 1 1 d . . .
O9 O 0.8317(2) 0.4098(3) 1.2381(3) 0.0854(13) Uani 1 1 d . . .
O10 O 0.7821(2) 0.5756(3) 1.2139(3) 0.0868(14) Uani 1 1 d . . .
O11 O 0.7121(3) 0.4406(4) 1.2307(4) 0.127(2) Uani 1 1 d . . .
O12 O 0.7630(3) 0.2801(3) 0.7071(2) 0.0946(16) Uani 1 1 d . . .
O13 O 0.7509(4) 0.4206(4) 0.7686(3) 0.1080(17) Uani 1 1 d . . .
O14 O 0.7429(2) 0.4449(3) 0.6581(2) 0.0696(11) Uani 1 1 d . . .
N1 N 0.53370(19) 0.4624(2) 0.87111(17) 0.0290(7) Uani 1 1 d . . .
N2 N 0.51207(19) 0.3556(2) 0.88028(18) 0.0301(7) Uani 1 1 d . . .
N3 N 0.4919(2) 0.1335(2) 0.88988(19) 0.0351(8) Uani 1 1 d . . .
N4 N 0.4941(2) 0.0192(2) 0.88820(19) 0.0353(8) Uani 1 1 d . . .
N5 N 0.7595(2) 0.8108(3) 1.0211(2) 0.0407(8) Uani 1 1 d . . .
N6 N 0.99344(19) 0.0339(2) 0.85714(17) 0.0299(7) Uani 1 1 d . . .
N7 N 0.97148(19) 0.1410(2) 0.86725(17) 0.0296(7) Uani 1 1 d . . .
N8 N 0.9514(2) 0.3606(3) 0.8781(2) 0.0392(8) Uani 1 1 d . . .
N9 N 0.9521(2) 0.4745(3) 0.8774(2) 0.0401(8) Uani 1 1 d . . .
N10 N 0.7559(2) 0.3075(3) 1.0279(2) 0.0401(8) Uani 1 1 d . . .
N11 N 0.7749(3) 0.4747(4) 1.2290(3) 0.0611(11) Uani 1 1 d . . .
N12 N 0.7519(2) 0.3812(3) 0.7112(2) 0.0517(10) Uani 1 1 d . . .
C1 C 0.5379(2) 0.5999(3) 0.9674(2) 0.0299(8) Uani 1 1 d . . .
C2 C 0.4936(2) 0.5575(3) 0.8894(2) 0.0305(8) Uani 1 1 d . . .
H2A H 0.4389 0.5359 0.8841 0.037 Uiso 1 1 calc R . .
H2B H 0.4896 0.6181 0.8548 0.037 Uiso 1 1 calc R . .
C3 C 0.6376(3) 0.5686(3) 0.8389(3) 0.0432(10) Uani 1 1 d . . .
H3A H 0.6573 0.6102 0.8843 0.052 Uiso 1 1 calc R . .
H3B H 0.5983 0.6130 0.8014 0.052 Uiso 1 1 calc R . .
H3C H 0.6820 0.5509 0.8237 0.052 Uiso 1 1 calc R . .
C4 C 0.5989(2) 0.4628(3) 0.8501(2) 0.0302(8) Uani 1 1 d . . .
C5 C 0.6195(2) 0.3514(3) 0.8452(2) 0.0345(9) Uani 1 1 d . . .
H5 H 0.6615 0.3245 0.8320 0.041 Uiso 1 1 calc R . .
C6 C 0.5639(2) 0.2879(3) 0.8644(2) 0.0313(8) Uani 1 1 d . . .
C7 C 0.5520(2) 0.1670(3) 0.8686(2) 0.0325(8) Uani 1 1 d . . .
C8 C 0.5931(3) 0.0745(3) 0.8541(2) 0.0387(10) Uani 1 1 d . . .
H8 H 0.6374 0.0758 0.8391 0.046 Uiso 1 1 calc R . .
C9 C 0.5538(3) -0.0184(3) 0.8667(2) 0.0363(9) Uani 1 1 d . . .
C10 C 0.5680(3) -0.1408(3) 0.8597(3) 0.0485(11) Uani 1 1 d . . .
H10A H 0.6146 -0.1505 0.8462 0.058 Uiso 1 1 calc R . .
H10B H 0.5213 -0.1732 0.8222 0.058 Uiso 1 1 calc R . .
H10C H 0.5773 -0.1775 0.9060 0.058 Uiso 1 1 calc R . .
C11 C 0.4335(3) -0.0450(4) 0.9056(3) 0.0503(12) Uani 1 1 d . . .
H11A H 0.4601 -0.0958 0.9456 0.060 Uiso 1 1 calc R . .
H11B H 0.4009 -0.0872 0.8629 0.060 Uiso 1 1 calc R . .
H11C H 0.3994 0.0054 0.9198 0.060 Uiso 1 1 calc R . .
C12 C 0.7110(2) 0.7547(3) 1.0457(2) 0.0369(9) Uani 1 1 d . . .
H12 H 0.7172 0.6770 1.0499 0.044 Uiso 1 1 calc R . .
C13 C 0.8167(3) 0.7545(5) 0.9945(3) 0.0575(13) Uani 1 1 d . . .
H13A H 0.7876 0.7063 0.9538 0.069 Uiso 1 1 calc R . .
H13B H 0.8539 0.7104 1.0337 0.069 Uiso 1 1 calc R . .
H13C H 0.8463 0.8097 0.9785 0.069 Uiso 1 1 calc R . .
C14 C 0.7538(3) 0.9327(4) 1.0168(3) 0.0586(14) Uani 1 1 d . . .
H14A H 0.7655 0.9631 1.0653 0.070 Uiso 1 1 calc R . .
H14B H 0.7000 0.9541 0.9853 0.070 Uiso 1 1 calc R . .
H14C H 0.7922 0.9613 0.9968 0.070 Uiso 1 1 calc R . .
C15 C 1.0223(3) -0.1066(3) 0.9583(2) 0.0351(9) Uani 1 1 d . . .
C16 C 0.9623(2) -0.0621(3) 0.8845(2) 0.0318(8) Uani 1 1 d . . .
H16A H 0.9497 -0.1219 0.8480 0.038 Uiso 1 1 calc R . .
H16B H 0.9123 -0.0408 0.8906 0.038 Uiso 1 1 calc R . .
C17 C 1.0873(3) -0.0711(3) 0.8120(2) 0.0421(10) Uani 1 1 d . . .
H17A H 1.0453 -0.1183 0.7795 0.050 Uiso 1 1 calc R . .
H17B H 1.1142 -0.1098 0.8579 0.050 Uiso 1 1 calc R . .
H17C H 1.1258 -0.0537 0.7894 0.050 Uiso 1 1 calc R . .
C18 C 1.0508(2) 0.0346(3) 0.8263(2) 0.0323(8) Uani 1 1 d . . .
C19 C 1.0657(2) 0.1455(3) 0.8152(2) 0.0336(9) Uani 1 1 d . . .
H19 H 1.1018 0.1724 0.7944 0.040 Uiso 1 1 calc R . .
C20 C 1.0157(2) 0.2092(3) 0.8413(2) 0.0296(8) Uani 1 1 d . . .
C21 C 1.0044(2) 0.3288(3) 0.8472(2) 0.0332(9) Uani 1 1 d . . .
C22 C 1.0388(3) 0.4229(3) 0.8265(2) 0.0389(10) Uani 1 1 d . . .
H22 H 1.0772 0.4234 0.8043 0.047 Uiso 1 1 calc R . .
C23 C 1.0036(3) 0.5146(3) 0.8464(2) 0.0402(10) Uani 1 1 d . . .
C24 C 1.0143(3) 0.6368(3) 0.8371(3) 0.0538(12) Uani 1 1 d . . .
H24A H 1.0335 0.6727 0.8846 0.065 Uiso 1 1 calc R . .
H24B H 0.9632 0.6691 0.8068 0.065 Uiso 1 1 calc R . .
H24C H 1.0531 0.6475 0.8138 0.065 Uiso 1 1 calc R . .
C25 C 0.9014(3) 0.5382(4) 0.9079(3) 0.0613(15) Uani 1 1 d . . .
H25A H 0.8820 0.4893 0.9371 0.074 Uiso 1 1 calc R . .
H25B H 0.8560 0.5695 0.8684 0.074 Uiso 1 1 calc R . .
H25C H 0.9327 0.5979 0.9385 0.074 Uiso 1 1 calc R . .
C26 C 0.7932(3) 0.2538(4) 0.9906(3) 0.0421(10) Uani 1 1 d . . .
H26 H 0.7810 0.1782 0.9800 0.051 Uiso 1 1 calc R . .
C27 C 0.6970(3) 0.2525(5) 1.0530(3) 0.0677(15) Uani 1 1 d . . .
H27A H 0.7228 0.1918 1.0857 0.081 Uiso 1 1 calc R . .
H27B H 0.6530 0.2236 1.0112 0.081 Uiso 1 1 calc R . .
H27C H 0.6763 0.3060 1.0787 0.081 Uiso 1 1 calc R . .
C28 C 0.7704(3) 0.4274(4) 1.0427(3) 0.0590(14) Uani 1 1 d . . .
H28A H 0.7557 0.4674 0.9967 0.071 Uiso 1 1 calc R . .
H28B H 0.8268 0.4396 1.0713 0.071 Uiso 1 1 calc R . .
H28C H 0.7382 0.4540 1.0697 0.071 Uiso 1 1 calc R . .
H1 H 0.794(3) 0.116(4) 0.839(3) 0.06(2) Uiso 1 1 d . . .
H4 H 0.785(5) 0.204(6) 0.794(5) 0.12(3) Uiso 1 1 d . . .
H6 H 0.690(3) 0.665(4) 1.199(3) 0.059(18) Uiso 1 1 d . . .
H7 H 0.671(3) 0.768(4) 1.209(3) 0.041(14) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r8 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r8'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r8'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.964(3) . ?
Cu1 O3 1.982(3) . ?
Cu1 O1 1.988(3) . ?
Cu1 N2 2.027(3) 3_667 ?
Cu1 N3 2.257(3) 3_667 ?
Cu2 O8 1.969(3) . ?
Cu2 N7 2.008(3) . ?
Cu2 O7 2.035(4) . ?
Cu2 O5 2.042(3) 3_757 ?
Cu2 N8 2.232(3) . ?
O1 C1 1.272(4) . ?
O2 C1 1.246(4) . ?
O3 H6 0.81(5) . ?
O3 H7 0.82(5) . ?
O4 C12 1.245(5) . ?
O5 C15 1.244(5) . ?
O5 Cu2 2.042(3) 3_757 ?
O6 C15 1.243(5) . ?
O7 H1 0.64(5) . ?
O7 H4 0.92(8) . ?
O8 C26 1.235(5) . ?
O9 N11 1.228(5) . ?
O10 N11 1.253(6) . ?
O11 N11 1.194(6) . ?
O12 N12 1.226(5) . ?
O13 N12 1.215(5) . ?
O14 N12 1.243(5) . ?
N1 N2 1.357(4) . ?
N1 C4 1.359(4) . ?
N1 C2 1.448(4) . ?
N2 C6 1.339(5) . ?
N2 Cu1 2.027(3) 3_667 ?
N3 C7 1.335(5) . ?
N3 N4 1.360(4) . ?
N3 Cu1 2.257(3) 3_667 ?
N4 C9 1.348(5) . ?
N4 C11 1.455(5) . ?
N5 C12 1.308(5) . ?
N5 C14 1.453(5) . ?
N5 C13 1.458(6) . ?
N6 C18 1.356(5) . ?
N6 N7 1.367(4) . ?
N6 C16 1.451(4) . ?
N7 C20 1.347(5) . ?
N8 C21 1.341(5) . ?
N8 N9 1.355(4) . ?
N9 C23 1.351(5) . ?
N9 C25 1.458(5) . ?
N10 C26 1.313(5) . ?
N10 C28 1.458(5) . ?
N10 C27 1.459(6) . ?
C1 C2 1.515(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.386(5) . ?
C5 C6 1.394(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(5) . ?
C7 C8 1.404(5) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.492(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.533(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.485(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.376(5) . ?
C19 C20 1.394(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.447(5) . ?
C21 C22 1.401(5) . ?
C22 C23 1.380(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.485(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O3 90.06(13) . . ?
O4 Cu1 O1 90.52(12) . . ?
O3 Cu1 O1 166.08(13) . . ?
O4 Cu1 N2 175.15(12) . 3_667 ?
O3 Cu1 N2 89.49(13) . 3_667 ?
O1 Cu1 N2 91.08(12) . 3_667 ?
O4 Cu1 N3 97.94(11) . 3_667 ?
O3 Cu1 N3 94.45(14) . 3_667 ?
O1 Cu1 N3 99.24(12) . 3_667 ?
N2 Cu1 N3 77.28(11) 3_667 3_667 ?
O8 Cu2 N7 173.27(12) . . ?
O8 Cu2 O7 88.79(14) . . ?
N7 Cu2 O7 93.79(14) . . ?
O8 Cu2 O5 89.59(12) . 3_757 ?
N7 Cu2 O5 90.59(12) . 3_757 ?
O7 Cu2 O5 155.78(14) . 3_757 ?
O8 Cu2 N8 96.02(12) . . ?
N7 Cu2 N8 77.28(12) . . ?
O7 Cu2 N8 106.36(15) . . ?
O5 Cu2 N8 97.84(12) 3_757 . ?
C1 O1 Cu1 105.1(2) . . ?
Cu1 O3 H6 113(4) . . ?
Cu1 O3 H7 111(3) . . ?
H6 O3 H7 106(5) . . ?
C12 O4 Cu1 125.5(3) . . ?
C15 O5 Cu2 100.2(3) . 3_757 ?
Cu2 O7 H1 107(5) . . ?
Cu2 O7 H4 117(5) . . ?
H1 O7 H4 117(7) . . ?
C26 O8 Cu2 122.7(3) . . ?
N2 N1 C4 110.7(3) . . ?
N2 N1 C2 120.8(3) . . ?
C4 N1 C2 128.3(3) . . ?
C6 N2 N1 106.4(3) . . ?
C6 N2 Cu1 118.1(2) . 3_667 ?
N1 N2 Cu1 135.6(2) . 3_667 ?
C7 N3 N4 105.0(3) . . ?
C7 N3 Cu1 110.3(2) . 3_667 ?
N4 N3 Cu1 144.6(2) . 3_667 ?
C9 N4 N3 111.8(3) . . ?
C9 N4 C11 128.9(3) . . ?
N3 N4 C11 119.3(3) . . ?
C12 N5 C14 119.3(4) . . ?
C12 N5 C13 122.0(4) . . ?
C14 N5 C13 118.6(4) . . ?
C18 N6 N7 110.9(3) . . ?
C18 N6 C16 127.9(3) . . ?
N7 N6 C16 120.9(3) . . ?
C20 N7 N6 105.8(3) . . ?
C20 N7 Cu2 118.2(2) . . ?
N6 N7 Cu2 135.5(2) . . ?
C21 N8 N9 105.5(3) . . ?
C21 N8 Cu2 110.7(2) . . ?
N9 N8 Cu2 143.5(3) . . ?
C23 N9 N8 111.5(3) . . ?
C23 N9 C25 128.0(3) . . ?
N8 N9 C25 120.4(3) . . ?
C26 N10 C28 119.8(4) . . ?
C26 N10 C27 122.2(4) . . ?
C28 N10 C27 117.9(4) . . ?
O11 N11 O9 120.3(5) . . ?
O11 N11 O10 120.5(5) . . ?
O9 N11 O10 119.1(5) . . ?
O13 N12 O12 119.6(5) . . ?
O13 N12 O14 119.1(5) . . ?
O12 N12 O14 121.2(4) . . ?
O2 C1 O1 124.3(4) . . ?
O2 C1 C2 120.5(3) . . ?
O1 C1 C2 115.2(3) . . ?
N1 C2 C1 112.6(3) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 106.9(3) . . ?
N1 C4 C3 122.3(3) . . ?
C5 C4 C3 130.8(3) . . ?
C4 C5 C6 105.7(3) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
N2 C6 C5 110.3(3) . . ?
N2 C6 C7 116.9(3) . . ?
C5 C6 C7 132.8(3) . . ?
N3 C7 C8 111.0(3) . . ?
N3 C7 C6 117.4(3) . . ?
C8 C7 C6 131.6(4) . . ?
C9 C8 C7 105.0(3) . . ?
C9 C8 H8 127.5 . . ?
C7 C8 H8 127.5 . . ?
N4 C9 C8 107.2(3) . . ?
N4 C9 C10 122.0(4) . . ?
C8 C9 C10 130.8(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N5 124.3(4) . . ?
O4 C12 H12 117.8 . . ?
N5 C12 H12 117.8 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 O5 125.1(4) . . ?
O6 C15 C16 119.2(3) . . ?
O5 C15 C16 115.7(4) . . ?
N6 C16 C15 112.9(3) . . ?
N6 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
N6 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 C19 107.0(3) . . ?
N6 C18 C17 121.6(3) . . ?
C19 C18 C17 131.4(4) . . ?
C18 C19 C20 106.3(3) . . ?
C18 C19 H19 126.9 . . ?
C20 C19 H19 126.9 . . ?
N7 C20 C19 110.1(3) . . ?
N7 C20 C21 116.5(3) . . ?
C19 C20 C21 133.4(3) . . ?
N8 C21 C22 110.6(3) . . ?
N8 C21 C20 116.9(3) . . ?
C22 C21 C20 132.5(4) . . ?
C23 C22 C21 105.2(4) . . ?
C23 C22 H22 127.4 . . ?
C21 C22 H22 127.4 . . ?
N9 C23 C22 107.1(3) . . ?
N9 C23 C24 122.5(4) . . ?
C22 C23 C24 130.4(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N9 C25 H25A 109.5 . . ?
N9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O8 C26 N10 123.9(4) . . ?
O8 C26 H26 118.0 . . ?
N10 C26 H26 118.0 . . ?
N10 C27 H27A 109.5 . . ?
N10 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N10 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N10 C28 H28A 109.5 . . ?
N10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Cu1 O1 C1 87.9(2) . . . . ?
O3 Cu1 O1 C1 -4.5(6) . . . . ?
N2 Cu1 O1 C1 -96.7(2) 3_667 . . . ?
N3 Cu1 O1 C1 -174.0(2) 3_667 . . . ?
O3 Cu1 O4 C12 86.9(4) . . . . ?
O1 Cu1 O4 C12 -79.2(4) . . . . ?
N2 Cu1 O4 C12 171.6(14) 3_667 . . . ?
N3 Cu1 O4 C12 -178.6(4) 3_667 . . . ?
N7 Cu2 O8 C26 173.1(10) . . . . ?
O7 Cu2 O8 C26 60.5(4) . . . . ?
O5 Cu2 O8 C26 -95.3(4) 3_757 . . . ?
N8 Cu2 O8 C26 166.8(4) . . . . ?
C4 N1 N2 C6 -0.4(4) . . . . ?
C2 N1 N2 C6 -175.2(3) . . . . ?
C4 N1 N2 Cu1 180.0(3) . . . 3_667 ?
C2 N1 N2 Cu1 5.2(5) . . . 3_667 ?
C7 N3 N4 C9 0.2(5) . . . . ?
Cu1 N3 N4 C9 176.7(4) 3_667 . . . ?
C7 N3 N4 C11 -177.4(4) . . . . ?
Cu1 N3 N4 C11 -0.9(7) 3_667 . . . ?
C18 N6 N7 C20 0.7(4) . . . . ?
C16 N6 N7 C20 175.0(3) . . . . ?
C18 N6 N7 Cu2 -170.3(3) . . . . ?
C16 N6 N7 Cu2 4.0(5) . . . . ?
O8 Cu2 N7 C20 -0.1(13) . . . . ?
O7 Cu2 N7 C20 112.3(3) . . . . ?
O5 Cu2 N7 C20 -91.6(3) 3_757 . . . ?
N8 Cu2 N7 C20 6.3(3) . . . . ?
O8 Cu2 N7 N6 170.2(10) . . . . ?
O7 Cu2 N7 N6 -77.5(4) . . . . ?
O5 Cu2 N7 N6 78.6(4) 3_757 . . . ?
N8 Cu2 N7 N6 176.5(4) . . . . ?
O8 Cu2 N8 C21 173.4(3) . . . . ?
N7 Cu2 N8 C21 -5.8(3) . . . . ?
O7 Cu2 N8 C21 -96.1(3) . . . . ?
O5 Cu2 N8 C21 83.0(3) 3_757 . . . ?
O8 Cu2 N8 N9 1.4(5) . . . . ?
N7 Cu2 N8 N9 -177.8(5) . . . . ?
O7 Cu2 N8 N9 91.9(5) . . . . ?
O5 Cu2 N8 N9 -89.0(5) 3_757 . . . ?
C21 N8 N9 C23 0.4(5) . . . . ?
Cu2 N8 N9 C23 172.7(4) . . . . ?
C21 N8 N9 C25 -179.4(4) . . . . ?
Cu2 N8 N9 C25 -7.2(7) . . . . ?
Cu1 O1 C1 O2 -3.0(4) . . . . ?
Cu1 O1 C1 C2 175.9(2) . . . . ?
N2 N1 C2 C1 93.7(4) . . . . ?
C4 N1 C2 C1 -80.1(5) . . . . ?
O2 C1 C2 N1 -8.2(5) . . . . ?
O1 C1 C2 N1 172.9(3) . . . . ?
N2 N1 C4 C5 0.3(4) . . . . ?
C2 N1 C4 C5 174.6(4) . . . . ?
N2 N1 C4 C3 -177.6(4) . . . . ?
C2 N1 C4 C3 -3.3(6) . . . . ?
N1 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
N1 N2 C6 C5 0.3(4) . . . . ?
Cu1 N2 C6 C5 180.0(3) 3_667 . . . ?
N1 N2 C6 C7 -178.6(3) . . . . ?
Cu1 N2 C6 C7 1.1(5) 3_667 . . . ?
C4 C5 C6 N2 -0.1(5) . . . . ?
C4 C5 C6 C7 178.6(4) . . . . ?
N4 N3 C7 C8 -0.6(5) . . . . ?
Cu1 N3 C7 C8 -178.5(3) 3_667 . . . ?
N4 N3 C7 C6 179.4(3) . . . . ?
Cu1 N3 C7 C6 1.5(4) 3_667 . . . ?
N2 C6 C7 N3 -1.8(6) . . . . ?
C5 C6 C7 N3 179.6(4) . . . . ?
N2 C6 C7 C8 178.2(4) . . . . ?
C5 C6 C7 C8 -0.4(8) . . . . ?
N3 C7 C8 C9 0.8(5) . . . . ?
C6 C7 C8 C9 -179.2(4) . . . . ?
N3 N4 C9 C8 0.3(5) . . . . ?
C11 N4 C9 C8 177.6(4) . . . . ?
N3 N4 C9 C10 -179.3(4) . . . . ?
C11 N4 C9 C10 -2.0(7) . . . . ?
C7 C8 C9 N4 -0.7(5) . . . . ?
C7 C8 C9 C10 178.9(4) . . . . ?
Cu1 O4 C12 N5 172.5(3) . . . . ?
C14 N5 C12 O4 2.5(7) . . . . ?
C13 N5 C12 O4 -174.5(4) . . . . ?
Cu2 O5 C15 O6 2.0(4) 3_757 . . . ?
Cu2 O5 C15 C16 -176.7(3) 3_757 . . . ?
C18 N6 C16 C15 74.3(5) . . . . ?
N7 N6 C16 C15 -99.0(4) . . . . ?
O6 C15 C16 N6 7.2(5) . . . . ?
O5 C15 C16 N6 -174.0(3) . . . . ?
N7 N6 C18 C19 -0.8(4) . . . . ?
C16 N6 C18 C19 -174.7(4) . . . . ?
N7 N6 C18 C17 177.8(3) . . . . ?
C16 N6 C18 C17 4.0(6) . . . . ?
N6 C18 C19 C20 0.6(5) . . . . ?
C17 C18 C19 C20 -177.8(4) . . . . ?
N6 N7 C20 C19 -0.3(4) . . . . ?
Cu2 N7 C20 C19 172.6(3) . . . . ?
N6 N7 C20 C21 -178.8(3) . . . . ?
Cu2 N7 C20 C21 -5.9(5) . . . . ?
C18 C19 C20 N7 -0.2(5) . . . . ?
C18 C19 C20 C21 178.0(4) . . . . ?
N9 N8 C21 C22 -0.1(5) . . . . ?
Cu2 N8 C21 C22 -175.2(3) . . . . ?
N9 N8 C21 C20 179.8(3) . . . . ?
Cu2 N8 C21 C20 4.7(4) . . . . ?
N7 C20 C21 N8 0.2(5) . . . . ?
C19 C20 C21 N8 -177.9(4) . . . . ?
N7 C20 C21 C22 -179.9(4) . . . . ?
C19 C20 C21 C22 2.0(8) . . . . ?
N8 C21 C22 C23 -0.2(5) . . . . ?
C20 C21 C22 C23 179.9(4) . . . . ?
N8 N9 C23 C22 -0.6(5) . . . . ?
C25 N9 C23 C22 179.2(4) . . . . ?
N8 N9 C23 C24 178.4(4) . . . . ?
C25 N9 C23 C24 -1.8(7) . . . . ?
C21 C22 C23 N9 0.4(5) . . . . ?
C21 C22 C23 C24 -178.4(5) . . . . ?
Cu2 O8 C26 N10 175.2(3) . . . . ?
C28 N10 C26 O8 2.9(7) . . . . ?
C27 N10 C26 O8 -179.7(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H6 O10 . . . 2.693(6) 0.81(6) 1.88(6) 177(5) no
O3 H7 O9 . . 2_657 2.720(5) 0.82(4) 1.99(5) 149(5) no
O7 H1 O14 . . 2_646 2.770(5) 0.64(5) 2.14(5) 167(8) no
O7 H4 O12 . . . 2.741(6) 0.92(8) 1.83(8) 176(7) no
