# 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 2016

####################################################################### 
# 
# 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_complex3
_database_code_depnum_ccdc_archive 'CCDC 1470944'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 N6 O19 Zn2'
_chemical_formula_weight         819.31

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.2276(15)
_cell_length_b                   9.4361(6)
_cell_length_c                   13.6952(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.6580(10)
_cell_angle_gamma                90
_cell_volume                     3249.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2759
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.567
_shelx_estimated_absorpt_T_min   0.539
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_T_max  0.6954
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9966
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3928
_reflns_number_gt                2944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+3.3789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3928
_refine_ls_number_parameters     227
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.21455(2) 1.11252(3) 0.29372(2) 0.02873(10) Uani 1 1 d . . . . .
C1 C -0.13568(9) 0.7869(3) 0.45926(18) 0.0286(5) Uani 1 1 d . . . . .
C2 C -0.07863(9) 0.8120(3) 0.43755(18) 0.0275(5) Uani 1 1 d . . . . .
C3 C -0.03996(10) 0.7114(3) 0.4626(2) 0.0373(6) Uani 1 1 d . . . . .
H1 H -0.0490 0.6294 0.4950 0.045 Uiso 1 1 calc R U . . .
C4 C 0.01207(10) 0.7313(3) 0.4402(2) 0.0380(7) Uani 1 1 d . . . . .
H2 H 0.0379 0.6640 0.4583 0.046 Uiso 1 1 calc R U . . .
C5 C 0.02502(9) 0.8514(3) 0.39080(18) 0.0264(5) Uani 1 1 d . . . . .
C6 C -0.01217(9) 0.9572(3) 0.36925(19) 0.0287(5) Uani 1 1 d . . . . .
H6 H -0.0027 1.0405 0.3388 0.034 Uiso 1 1 calc R U . . .
C7 C -0.06350(10) 0.9364(3) 0.39386(19) 0.0301(6) Uani 1 1 d . . . . .
H4 H -0.0886 1.0076 0.3808 0.036 Uiso 1 1 calc R U . . .
C8 C 0.09823(12) 0.6177(3) 0.3086(3) 0.0463(8) Uani 1 1 d . . . . .
H8A H 0.0615 0.6079 0.2848 0.069 Uiso 1 1 calc R U . . .
H8B H 0.1046 0.5666 0.3690 0.069 Uiso 1 1 calc R U . . .
H8C H 0.1204 0.5803 0.2610 0.069 Uiso 1 1 calc R U . . .
C9 C 0.11073(9) 0.7694(3) 0.32534(19) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.15455(9) 0.8470(3) 0.30520(18) 0.0252(5) Uani 1 1 d . . . . .
C11 C 0.20560(9) 0.8078(3) 0.26625(18) 0.0262(5) Uani 1 1 d . . . . .
N1 N 0.14620(8) 0.9847(2) 0.32676(16) 0.0281(5) Uani 1 1 d . . . . .
N2 N 0.07783(8) 0.8690(2) 0.36047(15) 0.0264(4) Uani 1 1 d . . . . .
N3 N 0.09954(8) 1.0004(2) 0.35987(16) 0.0299(5) Uani 1 1 d . . . . .
O1 O 0.18541(8) 1.1413(2) 0.14258(14) 0.0418(5) Uani 1 1 d . . . . .
H1B H 0.1515 1.1879 0.1396 0.063 Uiso 1 1 d R U . . .
H1C H 0.1816 1.0505 0.1112 0.063 Uiso 1 1 d R U . . .
O1W O 0.11841(12) 0.3833(3) 0.0841(2) 0.0864(9) Uani 1 1 d . . . . .
H1WA H 0.1483 0.3780 0.0451 0.130 Uiso 1 1 d R U . . .
H1WC H 0.1002 0.4715 0.0716 0.130 Uiso 1 1 d R U . . .
O2W O 0.2615(3) 0.2105(7) 0.9910(6) 0.099(2) Uani 0.5 1 d . U P . .
H2WB H 0.2457 0.1781 0.9289 0.148 Uiso 0.5 1 d R U P . .
H2WC H 0.2601 0.1363 1.0387 0.148 Uiso 0.5 1 d R U P . .
O2 O 0.17655(7) 1.30212(19) 0.32094(14) 0.0353(4) Uani 1 1 d . . . . .
H2A H 0.2000 1.3798 0.3108 0.053 Uiso 1 1 d R U . . .
H2B H 0.1672 1.3029 0.3875 0.053 Uiso 1 1 d R U . . .
O3 O 0.24718(7) 1.0864(2) 0.43951(14) 0.0371(4) Uani 1 1 d . . . . .
H3A H 0.2805 1.1357 0.4481 0.056 Uiso 1 1 d R U . . .
H3C H 0.2231 1.1248 0.4835 0.056 Uiso 1 1 d R U . . .
O3W O 0.05305(12) 0.2921(3) 0.2309(3) 0.1034(11) Uani 1 1 d . . . . .
H3WB H 0.0622 0.3809 0.2025 0.155 Uiso 1 1 d R U . . .
H3WC H 0.0837 0.2535 0.2677 0.155 Uiso 1 1 d R U . . .
O4 O 0.23831(7) 0.90825(18) 0.25929(14) 0.0314(4) Uani 1 1 d . . . . .
O5 O 0.21334(7) 0.68199(18) 0.24410(14) 0.0322(4) Uani 1 1 d . . . . .
O6 O -0.14733(7) 0.6674(2) 0.49235(14) 0.0368(4) Uani 1 1 d . . . . .
O7 O -0.16817(7) 0.8858(2) 0.44351(14) 0.0355(4) Uani 1 1 d . . . . .


_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
Zn1 O5 2.0396(17) 4 ?
Zn1 O2 2.0778(17) . ?
Zn1 O4 2.0839(17) . ?
Zn1 O3 2.1114(19) . ?
Zn1 O1 2.157(2) . ?
Zn1 N1 2.182(2) . ?
C1 O7 1.249(3) . ?
C1 O6 1.259(3) . ?
C1 C2 1.512(3) . ?
C2 C3 1.385(4) . ?
C2 C7 1.385(4) . ?
C3 C4 1.385(3) . ?
C3 H1 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H2 0.9300 . ?
C5 C6 1.385(3) . ?
C5 N2 1.437(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 H4 0.9300 . ?
C8 C9 1.479(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.367(3) . ?
C9 C10 1.372(3) . ?
C10 N1 1.353(3) . ?
C10 C11 1.481(3) . ?
C11 O5 1.244(3) . ?
C11 O4 1.265(3) . ?
N1 N3 1.304(3) . ?
N2 N3 1.356(3) . ?
O1 H1B 0.9600 . ?
O1 H1C 0.9602 . ?
O1W H1WA 0.9601 . ?
O1W H1WC 0.9600 . ?
O2W O2W 0.988(12) 7_557 ?
O2W H2WB 0.9600 . ?
O2W H2WC 0.9599 . ?
O2 H2A 0.9600 . ?
O2 H2B 0.9600 . ?
O3 H3A 0.9600 . ?
O3 H3C 0.9599 . ?
O3W H3WB 0.9600 . ?
O3W H3WC 0.9599 . ?
O5 Zn1 2.0395(16) 4_545 ?

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
O5 Zn1 O2 101.71(7) 4 . ?
O5 Zn1 O4 87.77(7) 4 . ?
O2 Zn1 O4 169.23(7) . . ?
O5 Zn1 O3 89.45(7) 4 . ?
O2 Zn1 O3 94.64(7) . . ?
O4 Zn1 O3 90.51(7) . . ?
O5 Zn1 O1 87.56(8) 4 . ?
O2 Zn1 O1 86.41(8) . . ?
O4 Zn1 O1 88.93(7) . . ?
O3 Zn1 O1 176.97(7) . . ?
O5 Zn1 N1 165.15(7) 4 . ?
O2 Zn1 N1 93.14(7) . . ?
O4 Zn1 N1 77.42(7) . . ?
O3 Zn1 N1 89.62(7) . . ?
O1 Zn1 N1 93.16(8) . . ?
O7 C1 O6 124.2(2) . . ?
O7 C1 C2 118.1(2) . . ?
O6 C1 C2 117.7(2) . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 120.4(2) . . ?
C7 C2 C1 121.2(2) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H1 119.5 . . ?
C4 C3 H1 119.5 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H2 120.4 . . ?
C3 C4 H2 120.4 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 N2 120.1(2) . . ?
C6 C5 N2 118.9(2) . . ?
C7 C6 C5 118.6(2) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 121.6(2) . . ?
C6 C7 H4 119.2 . . ?
C2 C7 H4 119.2 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 103.0(2) . . ?
N2 C9 C8 126.3(2) . . ?
C10 C9 C8 130.5(2) . . ?
N1 C10 C9 109.1(2) . . ?
N1 C10 C11 118.3(2) . . ?
C9 C10 C11 132.7(2) . . ?
O5 C11 O4 125.5(2) . . ?
O5 C11 C10 119.0(2) . . ?
O4 C11 C10 115.6(2) . . ?
N3 N1 C10 110.25(19) . . ?
N3 N1 Zn1 139.50(16) . . ?
C10 N1 Zn1 110.25(14) . . ?
N3 N2 C9 111.70(19) . . ?
N3 N2 C5 119.46(19) . . ?
C9 N2 C5 128.7(2) . . ?
N1 N3 N2 105.93(19) . . ?
Zn1 O1 H1B 109.4 . . ?
Zn1 O1 H1C 109.3 . . ?
H1B O1 H1C 109.5 . . ?
H1WA O1W H1WC 109.5 . . ?
O2W O2W H2WB 104.5 7_557 . ?
O2W O2W H2WC 109.0 7_557 . ?
H2WB O2W H2WC 109.5 . . ?
Zn1 O2 H2A 109.4 . . ?
Zn1 O2 H2B 109.3 . . ?
H2A O2 H2B 109.5 . . ?
Zn1 O3 H3A 109.3 . . ?
Zn1 O3 H3C 109.3 . . ?
H3A O3 H3C 109.5 . . ?
H3WB O3W H3WC 109.5 . . ?
C11 O4 Zn1 118.34(15) . . ?
C11 O5 Zn1 121.95(16) . 4_545 ?

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
O7 C1 C2 C3 173.6(3) . . . . ?
O6 C1 C2 C3 -6.2(4) . . . . ?
O7 C1 C2 C7 -5.3(4) . . . . ?
O6 C1 C2 C7 174.9(2) . . . . ?
C7 C2 C3 C4 -3.2(4) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 4.5(4) . . . . ?
C3 C4 C5 N2 -175.4(2) . . . . ?
C4 C5 C6 C7 -3.3(4) . . . . ?
N2 C5 C6 C7 176.6(2) . . . . ?
C5 C6 C7 C2 -1.2(4) . . . . ?
C3 C2 C7 C6 4.4(4) . . . . ?
C1 C2 C7 C6 -176.6(2) . . . . ?
N2 C9 C10 N1 -0.9(3) . . . . ?
C8 C9 C10 N1 175.3(3) . . . . ?
N2 C9 C10 C11 179.4(3) . . . . ?
C8 C9 C10 C11 -4.4(5) . . . . ?
N1 C10 C11 O5 -178.5(2) . . . . ?
C9 C10 C11 O5 1.2(4) . . . . ?
N1 C10 C11 O4 2.2(3) . . . . ?
C9 C10 C11 O4 -178.1(3) . . . . ?
C9 C10 N1 N3 0.1(3) . . . . ?
C11 C10 N1 N3 179.9(2) . . . . ?
C9 C10 N1 Zn1 -179.17(16) . . . . ?
C11 C10 N1 Zn1 0.6(3) . . . . ?
C10 C9 N2 N3 1.3(3) . . . . ?
C8 C9 N2 N3 -175.0(3) . . . . ?
C10 C9 N2 C5 177.8(2) . . . . ?
C8 C9 N2 C5 1.4(4) . . . . ?
C4 C5 N2 N3 -145.9(3) . . . . ?
C6 C5 N2 N3 34.2(3) . . . . ?
C4 C5 N2 C9 37.9(4) . . . . ?
C6 C5 N2 C9 -142.0(3) . . . . ?
C10 N1 N3 N2 0.7(3) . . . . ?
Zn1 N1 N3 N2 179.7(2) . . . . ?
C9 N2 N3 N1 -1.3(3) . . . . ?
C5 N2 N3 N1 -178.1(2) . . . . ?
O5 C11 O4 Zn1 176.7(2) . . . . ?
C10 C11 O4 Zn1 -4.0(3) . . . . ?
O4 C11 O5 Zn1 7.2(4) . . . 4_545 ?
C10 C11 O5 Zn1 -172.17(16) . . . 4_545 ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_complex1
_database_code_depnum_ccdc_archive 'CCDC 1470945'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H19 Cd N3 O10'
_chemical_formula_weight         465.69

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7880(5)
_cell_length_b                   8.7135(6)
_cell_length_c                   24.6516(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1672.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1778
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      21.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    1.363
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5790
_exptl_absorpt_correction_T_max  0.6469
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8060
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         24.373
_diffrn_reflns_theta_full        24.373
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2752
_reflns_number_gt                2308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 824 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2752
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.18824(6) 0.99091(6) 0.71328(2) 0.02666(15) Uani 1 1 d . . . . .
C1 C 0.2855(9) 0.6424(8) 0.6847(3) 0.0270(17) Uani 1 1 d . . . . .
C2 C 0.2718(9) 0.7170(7) 0.6310(3) 0.0231(17) Uani 1 1 d . . . . .
C3 C 0.3054(10) 0.6652(7) 0.5794(3) 0.0249(16) Uani 1 1 d . . . . .
C4 C 0.3747(9) 0.5181(9) 0.5594(3) 0.0379(18) Uani 1 1 d . . . . .
H4A H 0.2818 0.4486 0.5523 0.057 Uiso 1 1 calc R U . . .
H4B H 0.4493 0.4747 0.5863 0.057 Uiso 1 1 calc R U . . .
H4C H 0.4381 0.5354 0.5266 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2824(9) 0.8070(7) 0.4892(3) 0.0238(16) Uani 1 1 d . . . . .
C6 C 0.2246(11) 0.6977(8) 0.4540(3) 0.031(2) Uani 1 1 d . . . . .
H6 H 0.1781 0.6064 0.4668 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2363(9) 0.7253(8) 0.3987(3) 0.034(2) Uani 1 1 d . . . . .
H7 H 0.1960 0.6521 0.3744 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3562(9) 0.9437(8) 0.4710(3) 0.031(2) Uani 1 1 d . . . . .
H8 H 0.3977 1.0159 0.4955 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3662(8) 0.9691(8) 0.4163(3) 0.0319(19) Uani 1 1 d . . . . .
H9 H 0.4132 1.0604 0.4036 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3069(10) 0.8601(7) 0.3792(3) 0.0291(17) Uani 1 1 d . . . . .
N1 N 0.2157(8) 0.8646(6) 0.6275(2) 0.0284(15) Uani 1 1 d . . . . .
N2 N 0.2119(8) 0.9080(6) 0.5770(2) 0.0338(16) Uani 1 1 d . . . . .
N3 N 0.2673(7) 0.7868(6) 0.5474(2) 0.0265(15) Uani 1 1 d . . . . .
O1W O 0.4690(7) 0.8130(6) 0.0502(3) 0.0550(18) Uani 1 1 d . . . . .
H1WB H 0.5684 0.7767 0.0441 0.082 Uiso 1 1 d R U . . .
H1WC H 0.3937 0.7509 0.0376 0.082 Uiso 1 1 d R U . . .
O1 O 0.1794(8) 1.2209(6) 0.6619(2) 0.0579(17) Uani 1 1 d . . . . .
H1A H 0.1611 1.2962 0.6830 0.087 Uiso 1 1 d R U . . .
H1C H 0.0986 1.2150 0.6388 0.087 Uiso 1 1 d R U . . .
O2 O -0.0991(5) 1.0063(7) 0.70286(17) 0.0387(11) Uani 1 1 d . . . . .
H2A H -0.1461 1.0168 0.7338 0.058 Uiso 1 1 d R U . . .
H2C H -0.1356 0.9247 0.6879 0.058 Uiso 1 1 d R U . . .
O2W O 0.0848(8) 0.2348(6) 0.3456(2) 0.0549(17) Uani 1 1 d . . . . .
H2WB H 0.1470 0.1555 0.3500 0.082 Uiso 1 1 d R U . . .
H2WC H -0.0191 0.2077 0.3412 0.082 Uiso 1 1 d R U . . .
O3W O 0.1704(10) 0.3181(6) 0.4536(3) 0.059(2) Uani 1 1 d . . . . .
H3WA H 0.1943 0.3618 0.4237 0.088 Uiso 1 1 d R U . . .
H3WC H 0.0709 0.2784 0.4517 0.088 Uiso 1 1 d R U . . .
O3 O 0.4805(5) 1.0064(8) 0.7093(2) 0.0415(12) Uani 1 1 d . . . . .
H3B H 0.5132 1.0921 0.7221 0.062 Uiso 1 1 d R U . . .
H3C H 0.5235 0.9339 0.7279 0.062 Uiso 1 1 d R U . . .
O4 O 0.2328(6) 0.7196(5) 0.72484(19) 0.0332(13) Uani 1 1 d . . . . .
O7 O 0.3456(6) 0.5086(6) 0.68788(17) 0.0406(12) Uani 1 1 d . . . . .
C11 C 0.3139(11) 0.8956(8) 0.3194(3) 0.0328(19) Uani 1 1 d . . . . .
O5 O 0.3372(8) 1.0322(5) 0.3053(2) 0.0479(15) Uani 1 1 d . . . . .
O6 O 0.2909(7) 0.7917(5) 0.2861(2) 0.0470(14) Uani 1 1 d . . . . .


_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 O2 2.256(4) . ?
Cd1 O3 2.283(4) . ?
Cd1 O5 2.287(5) 2_575 ?
Cd1 O1 2.372(5) . ?
Cd1 N1 2.393(6) . ?
Cd1 O4 2.406(4) . ?
Cd1 O6 2.615(5) 2_575 ?
C1 O7 1.259(8) . ?
C1 O4 1.265(8) . ?
C1 C2 1.479(9) . ?
C2 N1 1.360(8) . ?
C2 C3 1.376(9) . ?
C3 N3 1.353(8) . ?
C3 C4 1.475(10) . ?
C5 C6 1.365(10) . ?
C5 C8 1.397(9) . ?
C5 N3 1.451(8) . ?
C6 C7 1.385(10) . ?
C7 C10 1.384(10) . ?
C8 C9 1.369(9) . ?
C9 C10 1.397(10) . ?
C10 C11 1.507(9) . ?
N1 N2 1.303(8) . ?
N2 N3 1.354(7) . ?
C11 O6 1.235(9) . ?
C11 O5 1.252(8) . ?
O5 Cd1 2.287(5) 2_574 ?
O6 Cd1 2.615(5) 2_574 ?

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
O2 Cd1 O3 168.68(17) . . ?
O2 Cd1 O5 91.9(2) . 2_575 ?
O3 Cd1 O5 97.7(2) . 2_575 ?
O2 Cd1 O1 81.9(2) . . ?
O3 Cd1 O1 87.5(2) . . ?
O5 Cd1 O1 127.00(19) 2_575 . ?
O2 Cd1 N1 90.88(19) . . ?
O3 Cd1 N1 84.24(19) . . ?
O5 Cd1 N1 147.56(18) 2_575 . ?
O1 Cd1 N1 85.4(2) . . ?
O2 Cd1 O4 102.4(2) . . ?
O3 Cd1 O4 85.4(2) . . ?
O5 Cd1 O4 78.97(16) 2_575 . ?
O1 Cd1 O4 153.83(18) . . ?
N1 Cd1 O4 68.88(17) . . ?
O2 Cd1 O6 95.55(18) . 2_575 ?
O3 Cd1 O6 85.71(19) . 2_575 ?
O5 Cd1 O6 52.27(17) 2_575 2_575 ?
O1 Cd1 O6 75.89(18) . 2_575 ?
N1 Cd1 O6 159.08(18) . 2_575 ?
O4 Cd1 O6 128.44(17) . 2_575 ?
O7 C1 O4 124.4(6) . . ?
O7 C1 C2 119.3(6) . . ?
O4 C1 C2 116.3(6) . . ?
N1 C2 C3 108.2(6) . . ?
N1 C2 C1 119.7(6) . . ?
C3 C2 C1 132.1(6) . . ?
N3 C3 C2 103.9(6) . . ?
N3 C3 C4 124.5(6) . . ?
C2 C3 C4 131.6(6) . . ?
C6 C5 C8 121.8(7) . . ?
C6 C5 N3 121.2(6) . . ?
C8 C5 N3 117.0(6) . . ?
C5 C6 C7 118.8(7) . . ?
C10 C7 C6 121.1(7) . . ?
C9 C8 C5 118.5(6) . . ?
C8 C9 C10 121.1(7) . . ?
C7 C10 C9 118.7(6) . . ?
C7 C10 C11 122.0(7) . . ?
C9 C10 C11 119.3(7) . . ?
N2 N1 C2 110.0(5) . . ?
N2 N1 Cd1 135.2(4) . . ?
C2 N1 Cd1 114.0(4) . . ?
N1 N2 N3 106.3(5) . . ?
C3 N3 N2 111.6(6) . . ?
C3 N3 C5 130.8(6) . . ?
N2 N3 C5 117.6(5) . . ?
C1 O4 Cd1 118.5(4) . . ?
O6 C11 O5 122.3(7) . . ?
O6 C11 C10 119.6(7) . . ?
O5 C11 C10 118.0(7) . . ?
C11 O5 Cd1 100.2(5) . 2_574 ?
C11 O6 Cd1 85.2(4) . 2_574 ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_complex2
_database_code_depnum_ccdc_archive 'CCDC 1470946'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 Co2 N6 O19'
_chemical_formula_weight         806.43

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.74(2)
_cell_length_b                   9.689(9)
_cell_length_c                   13.887(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.083(15)
_cell_angle_gamma                90
_cell_volume                     3450(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2742
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.54

_exptl_crystal_description       block
_exptl_crystal_colour            deepred
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    1.047
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_T_max  0.7373
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9828
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3830
_reflns_number_gt                3018
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+1.1610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3830
_refine_ls_number_parameters     272
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.28674(2) 0.38858(2) 0.20583(2) 0.02668(9) Uani 1 1 d . . . . .
O1 O 0.32218(6) 0.19674(14) 0.17927(10) 0.0361(3) Uani 1 1 d D . . . .
H1A H 0.3296(9) 0.183(2) 0.1227(9) 0.054 Uiso 1 1 d D U . . .
H1B H 0.3018(8) 0.1375(19) 0.1971(15) 0.054 Uiso 1 1 d D U . . .
O2 O 0.28598(5) 0.81438(13) 0.25565(10) 0.0319(3) Uani 1 1 d . . . . .
O3 O 0.31510(6) 0.35976(16) 0.35620(11) 0.0424(4) Uani 1 1 d D . . . .
H3A H 0.3232(9) 0.4352(14) 0.3810(17) 0.064 Uiso 1 1 d D U . . .
H3B H 0.3355(14) 0.297(2) 0.372(3) 0.064 Uiso 0.5 1 d D U P A 1
H3E H 0.2929(16) 0.317(3) 0.384(3) 0.064 Uiso 0.5 1 d D U P B 2
O4 O 0.25344(5) 0.41282(16) 0.06134(10) 0.0380(3) Uani 1 1 d D . . . .
H4A H 0.2746(7) 0.397(2) 0.0218(14) 0.057 Uiso 1 1 d D U . . .
H4B H 0.2245(5) 0.379(2) 0.0475(16) 0.057 Uiso 1 1 d D U . . .
O5 O 0.26202(5) 0.58822(13) 0.24153(10) 0.0313(3) Uani 1 1 d . . . . .
O6 O 0.66827(5) 0.61294(14) 0.05622(10) 0.0360(3) Uani 1 1 d . . . . .
O7 O 0.64770(5) 0.83132(15) 0.00798(10) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.42199(6) 0.63084(15) 0.13888(11) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.40052(6) 0.49942(16) 0.13958(11) 0.0293(4) Uani 1 1 d . . . . .
N3 N 0.35374(6) 0.51448(15) 0.17280(11) 0.0275(3) Uani 1 1 d . . . . .
C1 C 0.63580(7) 0.7118(2) 0.04065(13) 0.0285(4) Uani 1 1 d . . . . .
C2 C 0.57871(7) 0.6875(2) 0.06237(13) 0.0268(4) Uani 1 1 d . . . . .
C3 C 0.56356(7) 0.5632(2) 0.10592(13) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.5881 0.4936 0.1187 0.035 Uiso 1 1 calc R U . . .
C4 C 0.51209(7) 0.5428(2) 0.13018(13) 0.0289(4) Uani 1 1 d . . . . .
H4 H 0.5028 0.4614 0.1597 0.035 Uiso 1 1 calc R U . . .
C5 C 0.47491(7) 0.64841(19) 0.10889(13) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.48800(7) 0.7683(2) 0.05973(15) 0.0375(5) Uani 1 1 d . . . . .
H6A H 0.4627 0.8343 0.0420 0.045 Uiso 1 1 calc R U . . .
C7 C 0.54012(8) 0.7877(2) 0.03738(15) 0.0371(5) Uani 1 1 d . . . . .
H7A H 0.5490 0.8677 0.0058 0.045 Uiso 1 1 calc R U . . .
C8 C 0.38908(7) 0.72907(19) 0.17387(13) 0.0268(4) Uani 1 1 d . . . . .
C9 C 0.40116(9) 0.8806(2) 0.19100(18) 0.0453(6) Uani 1 1 d . . . . .
H9A H 0.3795 0.9164 0.2380 0.068 Uiso 1 1 calc R U . . .
H9B H 0.3945 0.9304 0.1314 0.068 Uiso 1 1 calc R U . . .
H9C H 0.4372 0.8909 0.2145 0.068 Uiso 1 1 calc R U . . .
C10 C 0.34533(7) 0.65158(18) 0.19445(13) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.29418(7) 0.68960(19) 0.23383(13) 0.0256(4) Uani 1 1 d . . . . .
O1W O 0.38132(10) 0.1143(2) 0.4170(2) 0.0909(7) Uani 1 1 d D . . . .
H1C H 0.3747(16) 0.0326(15) 0.427(3) 0.136 Uiso 1 1 d D U . . .
H1D H 0.3549(12) 0.163(4) 0.408(6) 0.136 Uiso 0.5 1 d D U P C 1
H1E H 0.400(3) 0.130(5) 0.373(4) 0.136 Uiso 0.5 1 d D U P D 2
O2W O 0.44583(11) 0.2069(3) 0.2696(2) 0.1067(8) Uani 1 1 d D . . . .
H2C H 0.4290(16) 0.230(5) 0.219(2) 0.160 Uiso 1 1 d D U . . .
H2D H 0.447(4) 0.125(2) 0.282(5) 0.160 Uiso 0.5 1 d D U P E 1
H2E H 0.4776(4) 0.208(9) 0.269(4) 0.160 Uiso 0.5 1 d D U P F 2
O3W O 0.2625(3) 0.2072(5) 0.4899(5) 0.103(2) Uani 0.5 1 d D U P . .
H3F H 0.254(4) 0.225(8) 0.544(3) 0.154 Uiso 0.5 1 d D U P . .
H3D H 0.264(4) 0.125(3) 0.476(6) 0.154 Uiso 0.5 1 d D U P . .


_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 O5 2.109(2) . ?
Co1 O1 2.117(2) . ?
Co1 O2 2.1176(18) 4_545 ?
Co1 O4 2.124(2) . ?
Co1 O3 2.168(2) . ?
Co1 N3 2.1937(19) . ?
O1 H1A 0.836(9) . ?
O1 H1B 0.830(9) . ?
O2 C11 1.269(2) . ?
O2 Co1 2.1176(18) 4 ?
O3 H3A 0.826(9) . ?
O3 H3B 0.823(10) . ?
O3 H3E 0.824(10) . ?
O4 H4A 0.822(9) . ?
O4 H4B 0.822(9) . ?
O5 C11 1.295(2) . ?
O6 C1 1.277(2) . ?
O7 C1 1.290(2) . ?
N1 N2 1.388(2) . ?
N1 C8 1.390(2) . ?
N1 C5 1.469(2) . ?
N2 N3 1.335(2) . ?
N3 C10 1.383(3) . ?
C1 C2 1.544(3) . ?
C2 C7 1.410(3) . ?
C2 C3 1.417(3) . ?
C3 C4 1.409(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(3) . ?
C6 C7 1.416(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C10 1.404(3) . ?
C8 C9 1.515(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.515(2) . ?
O1W H1C 0.824(10) . ?
O1W H1D 0.830(10) . ?
O1W H1E 0.820(10) . ?
O2W H2C 0.817(10) . ?
O2W H2D 0.816(10) . ?
O2W H2E 0.819(10) . ?
O3W O3W 1.103(12) 7_556 ?
O3W H3F 0.818(10) . ?
O3W H3D 0.819(10) . ?

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
O5 Co1 O1 171.79(6) . . ?
O5 Co1 O2 87.72(6) . 4_545 ?
O1 Co1 O2 98.63(7) . 4_545 ?
O5 Co1 O4 90.90(6) . . ?
O1 Co1 O4 94.39(7) . . ?
O2 Co1 O4 89.11(7) 4_545 . ?
O5 Co1 O3 88.54(6) . . ?
O1 Co1 O3 86.63(6) . . ?
O2 Co1 O3 86.72(7) 4_545 . ?
O4 Co1 O3 175.81(5) . . ?
O5 Co1 N3 78.36(7) . . ?
O1 Co1 N3 95.34(8) . . ?
O2 Co1 N3 166.03(5) 4_545 . ?
O4 Co1 N3 89.99(7) . . ?
O3 Co1 N3 93.96(7) . . ?
Co1 O1 H1A 116.3(17) . . ?
Co1 O1 H1B 105.2(16) . . ?
H1A O1 H1B 111.9(15) . . ?
C11 O2 Co1 123.60(11) . 4 ?
Co1 O3 H3A 109.8(18) . . ?
Co1 O3 H3B 120(3) . . ?
H3A O3 H3B 114.6(18) . . ?
Co1 O3 H3E 109(3) . . ?
H3A O3 H3E 113.9(18) . . ?
Co1 O4 H4A 112.0(17) . . ?
Co1 O4 H4B 117.3(16) . . ?
H4A O4 H4B 114.2(16) . . ?
C11 O5 Co1 117.90(12) . . ?
N2 N1 C8 111.72(14) . . ?
N2 N1 C5 119.21(14) . . ?
C8 N1 C5 128.96(15) . . ?
N3 N2 N1 105.90(14) . . ?
N2 N3 C10 110.08(14) . . ?
N2 N3 Co1 139.58(12) . . ?
C10 N3 Co1 110.33(11) . . ?
O6 C1 O7 124.08(17) . . ?
O6 C1 C2 118.16(17) . . ?
O7 C1 C2 117.75(16) . . ?
C7 C2 C3 118.40(17) . . ?
C7 C2 C1 120.54(17) . . ?
C3 C2 C1 121.05(16) . . ?
C4 C3 C2 121.39(17) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.80(17) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.87(17) . . ?
C6 C5 N1 120.16(16) . . ?
C4 C5 N1 118.96(16) . . ?
C5 C6 C7 119.31(18) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C2 C7 C6 120.98(18) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
N1 C8 C10 103.28(16) . . ?
N1 C8 C9 126.54(16) . . ?
C10 C8 C9 130.05(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C8 109.00(15) . . ?
N3 C10 C11 118.01(15) . . ?
C8 C10 C11 132.99(17) . . ?
O2 C11 O5 125.60(16) . . ?
O2 C11 C10 119.09(15) . . ?
O5 C11 C10 115.32(16) . . ?
H1C O1W H1D 113.3(19) . . ?
H1C O1W H1E 116(2) . . ?
H2C O2W H2D 117(2) . . ?
H2C O2W H2E 117(2) . . ?
O3W O3W H3F 53(7) 7_556 . ?
O3W O3W H3D 147(8) 7_556 . ?
H3F O3W H3D 116(2) . . ?

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
C8 N1 N2 N3 1.3(2) . . . . ?
C5 N1 N2 N3 177.79(15) . . . . ?
N1 N2 N3 C10 -0.85(19) . . . . ?
N1 N2 N3 Co1 -179.51(14) . . . . ?
O6 C1 C2 C7 -173.51(18) . . . . ?
O7 C1 C2 C7 6.6(3) . . . . ?
O6 C1 C2 C3 5.2(3) . . . . ?
O7 C1 C2 C3 -174.68(17) . . . . ?
C7 C2 C3 C4 -4.3(3) . . . . ?
C1 C2 C3 C4 176.94(17) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 3.5(3) . . . . ?
C3 C4 C5 N1 -176.66(16) . . . . ?
N2 N1 C5 C6 146.61(19) . . . . ?
C8 N1 C5 C6 -37.6(3) . . . . ?
N2 N1 C5 C4 -33.3(2) . . . . ?
C8 N1 C5 C4 142.5(2) . . . . ?
C4 C5 C6 C7 -4.5(3) . . . . ?
N1 C5 C6 C7 175.63(18) . . . . ?
C3 C2 C7 C6 3.3(3) . . . . ?
C1 C2 C7 C6 -177.99(19) . . . . ?
C5 C6 C7 C2 1.1(3) . . . . ?
N2 N1 C8 C10 -1.2(2) . . . . ?
C5 N1 C8 C10 -177.26(17) . . . . ?
N2 N1 C8 C9 174.90(19) . . . . ?
C5 N1 C8 C9 -1.1(3) . . . . ?
N2 N3 C10 C8 0.1(2) . . . . ?
Co1 N3 C10 C8 179.18(12) . . . . ?
N2 N3 C10 C11 -179.71(15) . . . . ?
Co1 N3 C10 C11 -0.6(2) . . . . ?
N1 C8 C10 N3 0.7(2) . . . . ?
C9 C8 C10 N3 -175.3(2) . . . . ?
N1 C8 C10 C11 -179.55(18) . . . . ?
C9 C8 C10 C11 4.5(4) . . . . ?
Co1 O2 C11 O5 -7.7(3) 4 . . . ?
Co1 O2 C11 C10 171.83(12) 4 . . . ?
Co1 O5 C11 O2 -177.39(15) . . . . ?
Co1 O5 C11 C10 3.1(2) . . . . ?
N3 C10 C11 O2 178.88(17) . . . . ?
C8 C10 C11 O2 -0.9(3) . . . . ?
N3 C10 C11 O5 -1.6(2) . . . . ?
C8 C10 C11 O5 178.70(19) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_complex4
_database_code_depnum_ccdc_archive 'CCDC 1470947'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 N6 Ni2 O19'
_chemical_formula_weight         805.99

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.1466(17)
_cell_length_b                   9.4725(6)
_cell_length_c                   13.6233(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.5320(10)
_cell_angle_gamma                90
_cell_volume                     3234.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2753
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             1672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    1.255
_shelx_estimated_absorpt_T_min   0.596
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5960
_exptl_absorpt_correction_T_max  0.6822
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10457
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         30.911
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4486
_reflns_number_gt                3819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+2.0970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     272
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.28744(2) 0.38672(2) 0.20683(2) 0.02345(6) Uani 1 1 d . . . . .
C1 C 0.63559(5) 0.71041(16) 0.04246(10) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.57826(5) 0.68530(15) 0.06374(10) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.56299(5) 0.55964(16) 0.10668(10) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.5881 0.4885 0.1194 0.032 Uiso 1 1 calc R U . . .
C4 C 0.51108(5) 0.53886(15) 0.13075(11) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.5013 0.4553 0.1603 0.032 Uiso 1 1 calc R U . . .
C5 C 0.47392(5) 0.64521(15) 0.10998(10) 0.0244(3) Uani 1 1 d . . . . .
C6 C 0.48713(6) 0.76639(17) 0.06133(13) 0.0349(3) Uani 1 1 d . . . . .
H6A H 0.4612 0.8337 0.0434 0.042 Uiso 1 1 calc R U . . .
C7 C 0.53967(6) 0.78648(17) 0.03951(12) 0.0344(3) Uani 1 1 d . . . . .
H7A H 0.5490 0.8690 0.0082 0.041 Uiso 1 1 calc R U . . .
C8 C 0.38748(5) 0.72599(14) 0.17485(10) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.39917(7) 0.87838(16) 0.19117(15) 0.0419(4) Uani 1 1 d . . . . .
H9A H 0.3770 0.9149 0.2394 0.063 Uiso 1 1 calc R U . . .
H9B H 0.3921 0.9288 0.1304 0.063 Uiso 1 1 calc R U . . .
H9C H 0.4360 0.8899 0.2142 0.063 Uiso 1 1 calc R U . . .
C10 C 0.34364(5) 0.64837(14) 0.19598(10) 0.0225(3) Uani 1 1 d . . . . .
C11 C 0.29204(5) 0.68515(14) 0.23481(10) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.42076(4) 0.62723(12) 0.14021(9) 0.0241(2) Uani 1 1 d . . . . .
N2 N 0.39953(4) 0.49527(12) 0.14151(9) 0.0264(2) Uani 1 1 d . . . . .
N3 N 0.35260(4) 0.51063(12) 0.17519(9) 0.0249(2) Uani 1 1 d . . . . .
O1 O 0.32327(4) 0.19769(11) 0.17799(8) 0.0311(2) Uani 1 1 d D . . . .
H1A H 0.3290(7) 0.187(2) 0.1197(8) 0.047 Uiso 1 1 d D U . . .
H1B H 0.3026(7) 0.1377(17) 0.1974(12) 0.047 Uiso 1 1 d D U . . .
O1W O 0.38178(8) 0.1142(2) 0.41763(18) 0.0827(6) Uani 1 1 d D . . . .
H1C H 0.3728(14) 0.0303(14) 0.420(3) 0.124 Uiso 1 1 d D U . . .
H1D H 0.3564(13) 0.169(3) 0.424(5) 0.124 Uiso 0.5 1 d D U P A 1
H1E H 0.400(3) 0.135(4) 0.372(4) 0.124 Uiso 0.5 1 d D U P B 2
O2 O 0.28356(4) 0.81059(10) 0.25642(8) 0.0281(2) Uani 1 1 d . . . . .
O2W O 0.44560(9) 0.2039(3) 0.26983(19) 0.1006(7) Uani 1 1 d D . . . .
H2C H 0.4284(13) 0.216(4) 0.2175(16) 0.151 Uiso 1 1 d D U . . .
H2D H 0.456(3) 0.124(3) 0.283(4) 0.151 Uiso 0.5 1 d D U P C 1
H2E H 0.4781(4) 0.201(9) 0.270(3) 0.151 Uiso 0.5 1 d D U P D 2
O3 O 0.31579(5) 0.35839(13) 0.35407(9) 0.0369(3) Uani 1 1 d D . . . .
H3A H 0.3239(8) 0.4346(12) 0.3802(14) 0.055 Uiso 1 1 d D U . . .
H3B H 0.3378(11) 0.295(2) 0.365(3) 0.055 Uiso 0.5 1 d D U P E 1
H3E H 0.2949(14) 0.311(3) 0.384(2) 0.055 Uiso 0.5 1 d D U P F 2
O3W O 0.2625(3) 0.2070(5) 0.4886(4) 0.1015(18) Uani 0.5 1 d D . P . .
H3F H 0.245(4) 0.230(8) 0.534(6) 0.152 Uiso 0.5 1 d D U P . .
H3D H 0.262(4) 0.123(2) 0.474(6) 0.152 Uiso 0.5 1 d D U P . .
O4 O 0.25425(4) 0.41313(12) 0.06404(8) 0.0328(2) Uani 1 1 d D . . . .
H4A H 0.2752(6) 0.394(2) 0.0228(12) 0.049 Uiso 1 1 d D U . . .
H4B H 0.2244(4) 0.381(2) 0.0522(14) 0.049 Uiso 1 1 d D U . . .
O5 O 0.26000(4) 0.58296(11) 0.24200(8) 0.0285(2) Uani 1 1 d . . . . .
O6 O 0.66817(4) 0.61112(11) 0.05699(8) 0.0329(2) Uani 1 1 d . . . . .
O7 O 0.64777(4) 0.83103(12) 0.01120(8) 0.0340(2) Uani 1 1 d . . . . .


_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
Ni1 O2 2.0249(9) 4_545 ?
Ni1 O5 2.0526(10) . ?
Ni1 O1 2.0563(10) . ?
Ni1 O4 2.0705(11) . ?
Ni1 N3 2.0879(11) . ?
Ni1 O3 2.0923(12) . ?
C1 O6 1.2529(17) . ?
C1 O7 1.2654(18) . ?
C1 C2 1.5114(17) . ?
C2 C7 1.385(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.3848(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3879(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(2) . ?
C5 N1 1.4398(16) . ?
C6 C7 1.3901(19) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 N1 1.3639(16) . ?
C8 C10 1.3745(18) . ?
C8 C9 1.486(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.3577(17) . ?
C10 C11 1.4809(17) . ?
C11 O2 1.2466(16) . ?
C11 O5 1.2682(16) . ?
N1 N2 1.3598(15) . ?
N2 N3 1.3078(15) . ?
O1 H1A 0.823(9) . ?
O1 H1B 0.828(9) . ?
O1W H1C 0.828(10) . ?
O1W H1D 0.832(10) . ?
O1W H1E 0.823(10) . ?
O2 Ni1 2.0249(9) 4 ?
O2W H2C 0.812(10) . ?
O2W H2D 0.816(10) . ?
O2W H2E 0.819(10) . ?
O3 H3A 0.823(9) . ?
O3 H3B 0.823(10) . ?
O3 H3E 0.825(10) . ?
O3W O3W 1.090(10) 7_556 ?
O3W H3F 0.817(10) . ?
O3W H3D 0.821(10) . ?
O4 H4A 0.821(9) . ?
O4 H4B 0.813(9) . ?

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
O2 Ni1 O5 86.88(4) 4_545 . ?
O2 Ni1 O1 98.36(4) 4_545 . ?
O5 Ni1 O1 173.54(4) . . ?
O2 Ni1 O4 88.71(4) 4_545 . ?
O5 Ni1 O4 89.53(5) . . ?
O1 Ni1 O4 94.35(5) . . ?
O2 Ni1 N3 166.64(4) 4_545 . ?
O5 Ni1 N3 79.80(4) . . ?
O1 Ni1 N3 95.00(4) . . ?
O4 Ni1 N3 90.16(4) . . ?
O2 Ni1 O3 87.57(5) 4_545 . ?
O5 Ni1 O3 89.30(5) . . ?
O1 Ni1 O3 87.15(5) . . ?
O4 Ni1 O3 176.15(4) . . ?
N3 Ni1 O3 93.24(5) . . ?
O6 C1 O7 123.93(12) . . ?
O6 C1 C2 118.25(13) . . ?
O7 C1 C2 117.82(13) . . ?
C7 C2 C3 118.68(12) . . ?
C7 C2 C1 120.41(13) . . ?
C3 C2 C1 120.90(12) . . ?
C4 C3 C2 121.13(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.73(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.21(12) . . ?
C6 C5 N1 120.01(12) . . ?
C4 C5 N1 118.77(12) . . ?
C5 C6 C7 119.07(14) . . ?
C5 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
C2 C7 C6 120.94(14) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
N1 C8 C10 103.28(11) . . ?
N1 C8 C9 126.76(12) . . ?
C10 C8 C9 129.84(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C8 108.74(11) . . ?
N3 C10 C11 117.72(11) . . ?
C8 C10 C11 133.54(12) . . ?
O2 C11 O5 125.99(12) . . ?
O2 C11 C10 118.66(12) . . ?
O5 C11 C10 115.34(12) . . ?
N2 N1 C8 111.96(10) . . ?
N2 N1 C5 119.12(11) . . ?
C8 N1 C5 128.81(11) . . ?
N3 N2 N1 105.57(10) . . ?
N2 N3 C10 110.44(11) . . ?
N2 N3 Ni1 138.99(9) . . ?
C10 N3 Ni1 110.57(8) . . ?
Ni1 O1 H1A 113.5(14) . . ?
Ni1 O1 H1B 104.0(14) . . ?
H1A O1 H1B 112.9(14) . . ?
H1C O1W H1D 112.4(18) . . ?
H1C O1W H1E 115.4(19) . . ?
C11 O2 Ni1 124.65(9) . 4 ?
H2C O2W H2D 118(2) . . ?
H2C O2W H2E 118(2) . . ?
Ni1 O3 H3A 110.8(15) . . ?
Ni1 O3 H3B 116(3) . . ?
H3A O3 H3B 115.1(17) . . ?
Ni1 O3 H3E 111(3) . . ?
H3A O3 H3E 114.1(17) . . ?
O3W O3W H3F 39(6) 7_556 . ?
O3W O3W H3D 142(6) 7_556 . ?
H3F O3W H3D 116(2) . . ?
Ni1 O4 H4A 112.5(14) . . ?
Ni1 O4 H4B 116.0(14) . . ?
H4A O4 H4B 114.4(14) . . ?
C11 O5 Ni1 116.47(8) . . ?

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
O6 C1 C2 C7 -173.40(15) . . . . ?
O7 C1 C2 C7 6.8(2) . . . . ?
O6 C1 C2 C3 5.7(2) . . . . ?
O7 C1 C2 C3 -174.13(13) . . . . ?
C7 C2 C3 C4 -4.1(2) . . . . ?
C1 C2 C3 C4 176.80(13) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 3.6(2) . . . . ?
C3 C4 C5 N1 -176.38(13) . . . . ?
C4 C5 C6 C7 -4.9(2) . . . . ?
N1 C5 C6 C7 175.11(15) . . . . ?
C3 C2 C7 C6 2.8(2) . . . . ?
C1 C2 C7 C6 -178.10(15) . . . . ?
C5 C6 C7 C2 1.6(3) . . . . ?
N1 C8 C10 N3 0.90(15) . . . . ?
C9 C8 C10 N3 -175.15(16) . . . . ?
N1 C8 C10 C11 -179.25(14) . . . . ?
C9 C8 C10 C11 4.7(3) . . . . ?
N3 C10 C11 O2 178.41(13) . . . . ?
C8 C10 C11 O2 -1.4(2) . . . . ?
N3 C10 C11 O5 -2.19(19) . . . . ?
C8 C10 C11 O5 177.97(15) . . . . ?
C10 C8 N1 N2 -1.23(16) . . . . ?
C9 C8 N1 N2 174.99(15) . . . . ?
C10 C8 N1 C5 -177.26(13) . . . . ?
C9 C8 N1 C5 -1.0(3) . . . . ?
C6 C5 N1 N2 147.44(15) . . . . ?
C4 C5 N1 N2 -32.55(19) . . . . ?
C6 C5 N1 C8 -36.8(2) . . . . ?
C4 C5 N1 C8 143.24(15) . . . . ?
C8 N1 N2 N3 1.08(16) . . . . ?
C5 N1 N2 N3 177.55(12) . . . . ?
N1 N2 N3 C10 -0.46(15) . . . . ?
N1 N2 N3 Ni1 179.72(11) . . . . ?
C8 C10 N3 N2 -0.29(16) . . . . ?
C11 C10 N3 N2 179.83(12) . . . . ?
C8 C10 N3 Ni1 179.58(9) . . . . ?
C11 C10 N3 Ni1 -0.30(15) . . . . ?
O5 C11 O2 Ni1 -7.8(2) . . . 4 ?
C10 C11 O2 Ni1 171.53(9) . . . 4 ?
O2 C11 O5 Ni1 -177.04(11) . . . . ?
C10 C11 O5 Ni1 3.61(16) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_complex5
_database_code_depnum_ccdc_archive 'CCDC 1470948'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Cu3 N6 O12'
_chemical_formula_weight         751.06

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.539(4)
_cell_length_b                   8.752(5)
_cell_length_c                   12.350(7)
_cell_angle_alpha                97.275(9)
_cell_angle_beta                 101.140(9)
_cell_angle_gamma                110.523(9)
_cell_volume                     634.7(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1472
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_F_000             377
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.570
_shelx_estimated_absorpt_T_min   0.391
_shelx_estimated_absorpt_T_max   0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3909
_exptl_absorpt_correction_T_max  0.6548
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3204
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2212
_reflns_number_gt                1848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2212
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1WC H 0.063(13) 0.729(10) 0.778(6) 0.15(4) Uiso 1 1 d . . . . .
H1WA H 0.188(10) 0.880(8) 0.788(5) 0.11(2) Uiso 1 1 d . . . . .
Cu1 Cu 0.0000 0.5000 1.0000 0.01904(14) Uani 1 2 d S . P . .
Cu2 Cu 0.51036(6) 0.69854(5) 1.01558(3) 0.01869(12) Uani 1 1 d . . . . .
C1 C 0.7594(5) 1.0207(4) 0.9869(2) 0.0190(7) Uani 1 1 d . . . . .
C2 C 0.3510(5) 0.6223(4) 0.2169(2) 0.0167(6) Uani 1 1 d . . . . .
C3 C 0.4089(5) 0.6505(4) 0.3444(2) 0.0163(6) Uani 1 1 d . . . . .
C4 C 0.6353(5) 0.7158(4) 0.4052(2) 0.0247(7) Uani 1 1 d . . . . .
H4 H 0.7481 0.7362 0.3668 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6932(5) 0.7507(4) 0.5227(2) 0.0249(7) Uani 1 1 d . . . . .
H5 H 0.8436 0.7906 0.5633 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5218(5) 0.7247(4) 0.5782(2) 0.0188(7) Uani 1 1 d . . . . .
C7 C 0.2963(5) 0.6591(4) 0.5195(2) 0.0229(7) Uani 1 1 d . . . . .
H7 H 0.1839 0.6418 0.5580 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2402(5) 0.6195(4) 0.4019(3) 0.0219(7) Uani 1 1 d . . . . .
H8 H 0.0892 0.5722 0.3616 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7103(5) 0.9272(4) 0.7668(2) 0.0186(6) Uani 1 1 d . . . . .
C10 C 0.6864(5) 0.9068(4) 0.8735(2) 0.0177(6) Uani 1 1 d . . . . .
C11 C 0.8481(6) 1.0722(4) 0.7266(3) 0.0315(8) Uani 1 1 d . . . . .
H11A H 0.8891 1.1726 0.7818 0.047 Uiso 1 1 calc R U . . .
H11B H 0.7620 1.0796 0.6565 0.047 Uiso 1 1 calc R U . . .
H11C H 0.9823 1.0582 0.7155 0.047 Uiso 1 1 calc R U . . .
N1 N 0.5511(4) 0.7450(3) 0.8661(2) 0.0186(6) Uani 1 1 d . . . . .
N2 N 0.4806(4) 0.6600(3) 0.7604(2) 0.0203(6) Uani 1 1 d . . . . .
N3 N 0.5796(4) 0.7720(3) 0.70049(19) 0.0180(6) Uani 1 1 d . . . . .
O1 O 0.2622(4) 0.4823(3) 0.9586(2) 0.0187(5) Uani 1 1 d . . . . .
H1 H 0.244(5) 0.473(4) 0.907(3) 0.005(10) Uiso 1 1 d . . . . .
O1W O 0.0949(6) 0.7865(5) 0.7384(2) 0.0491(8) Uani 1 1 d . . . . .
O2 O 0.7089(4) 0.9405(3) 1.06596(17) 0.0237(5) Uani 1 1 d . . . . .
O3 O 0.8488(4) 1.1739(3) 0.99931(18) 0.0310(6) Uani 1 1 d . . . . .
O4 O 0.1467(3) 0.5377(3) 0.16373(16) 0.0226(5) Uani 1 1 d . . . . .
O5 O 0.5108(4) 0.6919(3) 0.17309(16) 0.0227(5) Uani 1 1 d . . . . .


_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 O1 1.931(2) 2_567 ?
Cu1 O1 1.931(2) . ?
Cu1 O4 1.994(2) 2_566 ?
Cu1 O4 1.994(2) 1_556 ?
Cu2 O1 1.944(2) . ?
Cu2 O5 1.953(2) 1_556 ?
Cu2 N1 1.987(3) . ?
Cu2 O2 1.996(2) . ?
C1 O3 1.236(4) . ?
C1 O2 1.300(4) . ?
C1 C10 1.496(4) . ?
C2 O4 1.268(4) . ?
C2 O5 1.269(3) . ?
C2 C3 1.514(4) . ?
C3 C8 1.392(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.385(4) . ?
C6 N3 1.451(4) . ?
C7 C8 1.394(4) . ?
C9 N3 1.371(4) . ?
C9 C10 1.382(4) . ?
C9 C11 1.483(4) . ?
C10 N1 1.361(4) . ?
N1 N2 1.323(3) . ?
N2 N3 1.361(3) . ?
O4 Cu1 1.994(2) 1_554 ?
O5 Cu2 1.953(2) 1_554 ?

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 Cu1 O1 180.0 2_567 . ?
O1 Cu1 O4 91.48(10) 2_567 2_566 ?
O1 Cu1 O4 88.52(10) . 2_566 ?
O1 Cu1 O4 88.52(10) 2_567 1_556 ?
O1 Cu1 O4 91.48(10) . 1_556 ?
O4 Cu1 O4 180.0 2_566 1_556 ?
O1 Cu2 O5 93.36(10) . 1_556 ?
O1 Cu2 N1 96.60(10) . . ?
O5 Cu2 N1 170.00(10) 1_556 . ?
O1 Cu2 O2 166.78(9) . . ?
O5 Cu2 O2 88.38(9) 1_556 . ?
N1 Cu2 O2 81.75(9) . . ?
O3 C1 O2 125.7(3) . . ?
O3 C1 C10 121.7(3) . . ?
O2 C1 C10 112.5(3) . . ?
O4 C2 O5 125.8(3) . . ?
O4 C2 C3 117.5(2) . . ?
O5 C2 C3 116.6(3) . . ?
C8 C3 C4 119.7(3) . . ?
C8 C3 C2 120.8(3) . . ?
C4 C3 C2 119.4(3) . . ?
C5 C4 C3 120.5(3) . . ?
C6 C5 C4 118.7(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 N3 118.8(3) . . ?
C5 C6 N3 119.5(3) . . ?
C6 C7 C8 119.1(3) . . ?
C3 C8 C7 120.3(3) . . ?
N3 C9 C10 103.1(3) . . ?
N3 C9 C11 125.1(3) . . ?
C10 C9 C11 131.7(3) . . ?
N1 C10 C9 108.4(3) . . ?
N1 C10 C1 116.4(2) . . ?
C9 C10 C1 135.0(3) . . ?
N2 N1 C10 111.0(2) . . ?
N2 N1 Cu2 136.8(2) . . ?
C10 N1 Cu2 112.19(18) . . ?
N1 N2 N3 104.7(2) . . ?
N2 N3 C9 112.7(2) . . ?
N2 N3 C6 119.6(2) . . ?
C9 N3 C6 127.3(2) . . ?
Cu1 O1 Cu2 107.74(11) . . ?
C1 O2 Cu2 116.42(19) . . ?
C2 O4 Cu1 128.93(19) . 1_554 ?
C2 O5 Cu2 130.51(19) . 1_554 ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.073

