# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1406556'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 Cu N4 O4'
_chemical_formula_weight         501.97

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.9763(5)
_cell_length_b                   10.5573(3)
_cell_length_c                   27.4132(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4334.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9511
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.57

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             2056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.050
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7942
_exptl_absorpt_correction_T_max  0.8341
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91187
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.475
_diffrn_reflns_theta_max         25.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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             4136
_reflns_number_gt                2728
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0530P)²+2.6457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4136
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
C1 C -0.0695(2) 0.0143(3) 0.36751(12) 0.0462(8) Uani 1 1 d . . . . .
C2 C -0.1215(2) 0.0814(4) 0.33414(14) 0.0614(10) Uani 1 1 d . . . . .
H2 H -0.1028 0.1584 0.3212 0.074 Uiso 1 1 calc R U . . .
C3 C -0.2022(3) 0.0274(5) 0.32130(17) 0.0747(13) Uani 1 1 d . . . . .
H3 H -0.2388 0.0693 0.2992 0.090 Uiso 1 1 calc R U . . .
C4 C -0.2302(3) -0.0874(5) 0.34048(17) 0.0791(13) Uani 1 1 d . . . . .
H4 H -0.2858 -0.1189 0.3315 0.095 Uiso 1 1 calc R U . . .
C5 C -0.1792(3) -0.1553(4) 0.37196(15) 0.0660(11) Uani 1 1 d . . . . .
H5 H -0.1978 -0.2332 0.3841 0.079 Uiso 1 1 calc R U . . .
C6 C -0.0975(2) -0.1018(3) 0.38504(12) 0.0489(8) Uani 1 1 d . . . . .
C7 C 0.0322(2) -0.0525(3) 0.41845(11) 0.0399(7) Uani 1 1 d . . . . .
C8 C 0.10945(19) -0.0529(3) 0.45124(11) 0.0391(7) Uani 1 1 d . . . . .
C9 C 0.1051(2) -0.1191(3) 0.49508(12) 0.0486(8) Uani 1 1 d . . . . .
H9 H 0.0535 -0.1641 0.5026 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1754(2) -0.1198(4) 0.52767(13) 0.0563(9) Uani 1 1 d . . . . .
H10 H 0.1715 -0.1668 0.5563 0.068 Uiso 1 1 calc R U . . .
C11 C 0.2503(3) -0.0513(4) 0.51781(13) 0.0597(10) Uani 1 1 d . . . . .
H11 H 0.2978 -0.0516 0.5397 0.072 Uiso 1 1 calc R U . . .
C12 C 0.2558(2) 0.0187(3) 0.47529(13) 0.0526(9) Uani 1 1 d . . . . .
H12 H 0.3065 0.0671 0.4694 0.063 Uiso 1 1 calc R U . . .
C13 C 0.1871(2) 0.0181(3) 0.44121(12) 0.0400(7) Uani 1 1 d . . . . .
C14 C 0.2717(2) 0.1090(3) 0.37845(11) 0.0401(7) Uani 1 1 d . . . . .
H14 H 0.3165 0.0546 0.3891 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2960(2) 0.1975(3) 0.34170(11) 0.0384(7) Uani 1 1 d . . . . .
C16 C 0.3858(2) 0.1932(3) 0.32120(11) 0.0385(7) Uani 1 1 d . . . . .
C17 C 0.4463(2) 0.0949(3) 0.32994(12) 0.0490(8) Uani 1 1 d . . . . .
H17 H 0.4288 0.0264 0.3490 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5311(2) 0.0979(4) 0.31087(14) 0.0567(9) Uani 1 1 d . . . . .
H18 H 0.5708 0.0330 0.3182 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5584(2) 0.1960(4) 0.28084(14) 0.0583(10) Uani 1 1 d . . . . .
H19 H 0.6158 0.1966 0.2680 0.070 Uiso 1 1 calc R U . . .
C20 C 0.5012(2) 0.2907(3) 0.27037(13) 0.0548(9) Uani 1 1 d . . . . .
H20 H 0.5193 0.3561 0.2499 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4140(2) 0.2920(3) 0.29002(12) 0.0447(8) Uani 1 1 d . . . . .
C22 C 0.3528(3) 0.3901(3) 0.27854(14) 0.0584(10) Uani 1 1 d . . . . .
H22 H 0.3717 0.4563 0.2587 0.070 Uiso 1 1 calc R U . . .
C23 C 0.2688(2) 0.3909(3) 0.29534(13) 0.0550(9) Uani 1 1 d . . . . .
H23 H 0.2303 0.4555 0.2858 0.066 Uiso 1 1 calc R U . . .
C24 C 0.2374(2) 0.2953(3) 0.32729(11) 0.0437(8) Uani 1 1 d . . . . .
C25 C -0.0321(3) -0.2721(4) 0.43732(15) 0.0690(12) Uani 1 1 d . . . . .
H25A H 0.0283 -0.2999 0.4422 0.103 Uiso 1 1 calc R U . . .
H25B H -0.0618 -0.3289 0.4153 0.103 Uiso 1 1 calc R U . . .
H25C H -0.0630 -0.2713 0.4680 0.103 Uiso 1 1 calc R U . . .
Cu1 Cu 0.08873(2) 0.18849(4) 0.37758(2) 0.04235(14) Uani 1 1 d . . . . .
N1 N 0.01194(16) 0.0435(3) 0.38885(9) 0.0418(6) Uani 1 1 d . . . . .
N2 N -0.03181(18) -0.1442(3) 0.41656(10) 0.0465(7) Uani 1 1 d . . . . .
N3 N 0.19381(16) 0.0956(2) 0.39886(9) 0.0397(6) Uani 1 1 d . . . . .
N4 N -0.0177(2) 0.3568(3) 0.41609(16) 0.0644(10) Uani 1 1 d . . . . .
O1 O 0.15532(15) 0.3069(2) 0.34232(9) 0.0569(6) Uani 1 1 d . . . . .
O2 O 0.0432(2) 0.3261(3) 0.44427(11) 0.0859(9) Uani 1 1 d . . . . .
O3 O -0.01672(16) 0.3079(2) 0.37402(11) 0.0599(7) Uani 1 1 d . . . . .
O4 O -0.0767(2) 0.4301(3) 0.42716(17) 0.1240(15) 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
C1 C6 1.382(5) . ?
C1 N1 1.388(4) . ?
C1 C2 1.395(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.383(4) . ?
C7 N1 1.334(4) . ?
C7 N2 1.363(4) . ?
C7 C8 1.465(4) . ?
C8 C9 1.392(4) . ?
C8 C13 1.410(4) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 N3 1.423(4) . ?
C14 N3 1.302(4) . ?
C14 C15 1.421(4) . ?
C14 H14 0.9300 . ?
C15 C24 1.412(4) . ?
C15 C16 1.458(4) . ?
C16 C17 1.398(4) . ?
C16 C21 1.413(4) . ?
C17 C18 1.374(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.347(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.413(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.418(5) . ?
C22 C23 1.341(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.417(4) . ?
C23 H23 0.9300 . ?
C24 O1 1.302(4) . ?
C25 N2 1.466(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
Cu1 O1 1.868(2) . ?
Cu1 N1 1.939(3) . ?
Cu1 N3 1.944(2) . ?
Cu1 O3 2.023(2) . ?
Cu1 O2 2.433(3) . ?
N4 O4 1.213(4) . ?
N4 O2 1.239(4) . ?
N4 O3 1.264(4) . ?

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
C6 C1 N1 108.5(3) . . ?
C6 C1 C2 120.6(3) . . ?
N1 C1 C2 130.9(3) . . ?
C3 C2 C1 116.5(4) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 116.3(4) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C1 C6 N2 106.8(3) . . ?
C1 C6 C5 122.4(4) . . ?
N2 C6 C5 130.8(4) . . ?
N1 C7 N2 110.9(3) . . ?
N1 C7 C8 123.7(3) . . ?
N2 C7 C8 125.2(3) . . ?
C9 C8 C13 118.3(3) . . ?
C9 C8 C7 119.6(3) . . ?
C13 C8 C7 122.0(3) . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.8(3) . . ?
C12 C13 N3 119.6(3) . . ?
C8 C13 N3 121.5(3) . . ?
N3 C14 C15 127.3(3) . . ?
N3 C14 H14 116.4 . . ?
C15 C14 H14 116.4 . . ?
C24 C15 C14 121.3(3) . . ?
C24 C15 C16 119.3(3) . . ?
C14 C15 C16 119.3(3) . . ?
C17 C16 C21 117.3(3) . . ?
C17 C16 C15 123.7(3) . . ?
C21 C16 C15 119.0(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C20 119.9(3) . . ?
C16 C21 C22 118.8(3) . . ?
C20 C21 C22 121.3(3) . . ?
C23 C22 C21 122.3(3) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
O1 C24 C15 124.6(3) . . ?
O1 C24 C23 116.2(3) . . ?
C15 C24 C23 119.2(3) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 Cu1 N1 157.96(11) . . ?
O1 Cu1 N3 93.48(10) . . ?
N1 Cu1 N3 91.95(10) . . ?
O1 Cu1 O3 88.57(10) . . ?
N1 Cu1 O3 92.09(10) . . ?
N3 Cu1 O3 163.91(12) . . ?
O1 Cu1 O2 97.98(11) . . ?
N1 Cu1 O2 100.69(11) . . ?
N3 Cu1 O2 107.62(12) . . ?
O3 Cu1 O2 56.31(11) . . ?
C7 N1 C1 106.7(3) . . ?
C7 N1 Cu1 124.2(2) . . ?
C1 N1 Cu1 129.0(2) . . ?
C7 N2 C6 107.1(3) . . ?
C7 N2 C25 129.9(3) . . ?
C6 N2 C25 122.6(3) . . ?
C14 N3 C13 118.5(3) . . ?
C14 N3 Cu1 122.8(2) . . ?
C13 N3 Cu1 118.51(19) . . ?
O4 N4 O2 123.2(5) . . ?
O4 N4 O3 119.9(4) . . ?
O2 N4 O3 116.9(3) . . ?
C24 O1 Cu1 127.2(2) . . ?
N4 O2 Cu1 83.9(2) . . ?
N4 O3 Cu1 102.7(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
C6 C1 C2 C3 2.0(5) . . . . ?
N1 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
N1 C1 C6 N2 -1.0(4) . . . . ?
C2 C1 C6 N2 179.3(3) . . . . ?
N1 C1 C6 C5 177.3(3) . . . . ?
C2 C1 C6 C5 -2.4(5) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 N2 178.4(4) . . . . ?
N1 C7 C8 C9 149.4(3) . . . . ?
N2 C7 C8 C9 -25.3(5) . . . . ?
N1 C7 C8 C13 -26.9(5) . . . . ?
N2 C7 C8 C13 158.4(3) . . . . ?
C13 C8 C9 C10 -2.1(5) . . . . ?
C7 C8 C9 C10 -178.5(3) . . . . ?
C8 C9 C10 C11 2.0(6) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 -1.9(6) . . . . ?
C11 C12 C13 C8 1.7(5) . . . . ?
C11 C12 C13 N3 177.4(3) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C7 C8 C13 C12 176.5(3) . . . . ?
C9 C8 C13 N3 -175.4(3) . . . . ?
C7 C8 C13 N3 0.9(5) . . . . ?
N3 C14 C15 C24 8.4(5) . . . . ?
N3 C14 C15 C16 -176.4(3) . . . . ?
C24 C15 C16 C17 -174.6(3) . . . . ?
C14 C15 C16 C17 10.2(5) . . . . ?
C24 C15 C16 C21 4.4(4) . . . . ?
C14 C15 C16 C21 -170.9(3) . . . . ?
C21 C16 C17 C18 3.2(5) . . . . ?
C15 C16 C17 C18 -177.9(3) . . . . ?
C16 C17 C18 C19 -2.5(6) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C17 C16 C21 C20 -2.0(5) . . . . ?
C15 C16 C21 C20 179.0(3) . . . . ?
C17 C16 C21 C22 177.1(3) . . . . ?
C15 C16 C21 C22 -1.9(5) . . . . ?
C19 C20 C21 C16 0.1(5) . . . . ?
C19 C20 C21 C22 -179.0(4) . . . . ?
C16 C21 C22 C23 -1.6(6) . . . . ?
C20 C21 C22 C23 177.5(4) . . . . ?
C21 C22 C23 C24 2.5(6) . . . . ?
C14 C15 C24 O1 -6.4(5) . . . . ?
C16 C15 C24 O1 178.4(3) . . . . ?
C14 C15 C24 C23 171.7(3) . . . . ?
C16 C15 C24 C23 -3.5(5) . . . . ?
C22 C23 C24 O1 178.4(4) . . . . ?
C22 C23 C24 C15 0.1(5) . . . . ?
N2 C7 N1 C1 1.1(3) . . . . ?
C8 C7 N1 C1 -174.2(3) . . . . ?
N2 C7 N1 Cu1 -176.1(2) . . . . ?
C8 C7 N1 Cu1 8.6(4) . . . . ?
C6 C1 N1 C7 -0.1(3) . . . . ?
C2 C1 N1 C7 179.5(4) . . . . ?
C6 C1 N1 Cu1 177.0(2) . . . . ?
C2 C1 N1 Cu1 -3.4(5) . . . . ?
N1 C7 N2 C6 -1.8(4) . . . . ?
C8 C7 N2 C6 173.5(3) . . . . ?
N1 C7 N2 C25 170.8(3) . . . . ?
C8 C7 N2 C25 -13.9(5) . . . . ?
C1 C6 N2 C7 1.7(4) . . . . ?
C5 C6 N2 C7 -176.4(4) . . . . ?
C1 C6 N2 C25 -171.6(3) . . . . ?
C5 C6 N2 C25 10.3(6) . . . . ?
C15 C14 N3 C13 -168.3(3) . . . . ?
C15 C14 N3 Cu1 5.9(5) . . . . ?
C12 C13 N3 C14 37.0(4) . . . . ?
C8 C13 N3 C14 -147.4(3) . . . . ?
C12 C13 N3 Cu1 -137.5(3) . . . . ?
C8 C13 N3 Cu1 38.1(4) . . . . ?
C15 C24 O1 Cu1 -10.5(5) . . . . ?
C23 C24 O1 Cu1 171.4(2) . . . . ?
N1 Cu1 O1 C24 -85.3(4) . . . . ?
N3 Cu1 O1 C24 18.6(3) . . . . ?
O3 Cu1 O1 C24 -177.3(3) . . . . ?
O2 Cu1 O1 C24 127.0(3) . . . . ?
O4 N4 O2 Cu1 177.1(3) . . . . ?
O3 N4 O2 Cu1 -2.8(3) . . . . ?
O4 N4 O3 Cu1 -176.5(3) . . . . ?
O2 N4 O3 Cu1 3.5(4) . . . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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 1406557'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 Cu N4 O4'
_chemical_formula_sum            'C27 H22 Cu N4 O4'
_chemical_formula_weight         530.02

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                   9.9413(7)
_cell_length_b                   15.3917(10)
_cell_length_c                   17.7468(11)
_cell_angle_alpha                69.236(3)
_cell_angle_beta                 85.698(5)
_cell_angle_gamma                72.483(3)
_cell_volume                     2419.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.33

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.944
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31610
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.744
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             8595
_reflns_number_gt                5497
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1368P)²+9.3101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8595
_refine_ls_number_parameters     649
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.2796
_refine_ls_wR_factor_gt          0.2552
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.4355(8) 0.3871(6) 0.4139(5) 0.053(2) Uani 1 1 d . . . . .
C2 C 0.3023(10) 0.4535(7) 0.3830(6) 0.073(3) Uani 1 1 d . . . . .
H2 H 0.2724 0.4633 0.3315 0.088 Uiso 1 1 calc R U . . .
C3 C 0.2181(10) 0.5027(7) 0.4261(7) 0.083(3) Uani 1 1 d . . . . .
H3 H 0.1335 0.5482 0.4022 0.100 Uiso 1 1 calc R U . . .
C4 C 0.2518(9) 0.4887(6) 0.5051(6) 0.058(2) Uani 1 1 d . . . . .
C5 C 0.1596(12) 0.5399(7) 0.5507(8) 0.092(4) Uani 1 1 d . . . . .
H5 H 0.0728 0.5830 0.5280 0.110 Uiso 1 1 calc R U . . .
C6 C 0.1970(13) 0.5264(7) 0.6271(7) 0.091(4) Uani 1 1 d . . . . .
H6 H 0.1344 0.5595 0.6563 0.109 Uiso 1 1 calc R U . . .
C7 C 0.3262(12) 0.4643(6) 0.6621(6) 0.072(3) Uani 1 1 d . . . . .
H7 H 0.3516 0.4571 0.7138 0.086 Uiso 1 1 calc R U . . .
C8 C 0.4178(10) 0.4128(6) 0.6192(5) 0.060(2) Uani 1 1 d . . . . .
H8 H 0.5037 0.3698 0.6433 0.071 Uiso 1 1 calc R U . . .
C9 C 0.3842(9) 0.4238(5) 0.5412(5) 0.051(2) Uani 1 1 d . . . . .
C10 C 0.4769(7) 0.3681(5) 0.4942(5) 0.0431(17) Uani 1 1 d . . . . .
C11 C 0.5948(8) 0.2920(5) 0.5345(4) 0.0430(17) Uani 1 1 d . . . . .
H11 H 0.6064 0.2794 0.5892 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7840(8) 0.1500(5) 0.5558(4) 0.0436(17) Uani 1 1 d . . . . .
C13 C 0.7330(9) 0.0925(6) 0.6239(5) 0.057(2) Uani 1 1 d . . . . .
H13 H 0.6384 0.1125 0.6357 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8209(10) 0.0059(7) 0.6745(5) 0.066(2) Uani 1 1 d . . . . .
H14 H 0.7855 -0.0315 0.7204 0.079 Uiso 1 1 calc R U . . .
C15 C 0.9598(9) -0.0249(6) 0.6570(5) 0.060(2) Uani 1 1 d . . . . .
H15 H 1.0197 -0.0825 0.6913 0.071 Uiso 1 1 calc R U . . .
C16 C 1.0091(9) 0.0294(6) 0.5891(5) 0.056(2) Uani 1 1 d . . . . .
H16 H 1.1025 0.0064 0.5766 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9264(8) 0.1182(6) 0.5372(4) 0.0462(18) Uani 1 1 d . . . . .
C18 C 0.9793(7) 0.1741(6) 0.4632(5) 0.0479(19) Uani 1 1 d . . . . .
C20 C 1.1312(9) 0.2251(6) 0.3726(6) 0.062(2) Uani 1 1 d . . . . .
C21 C 1.2490(11) 0.2456(9) 0.3310(9) 0.088(3) Uani 1 1 d . . . . .
H21 H 1.3365 0.2274 0.3566 0.105 Uiso 1 1 calc R U . . .
C22 C 1.2262(15) 0.2950(10) 0.2487(10) 0.112(5) Uani 1 1 d . . . . .
H22 H 1.3019 0.3088 0.2177 0.135 Uiso 1 1 calc R U . . .
C23 C 1.1018(16) 0.3229(8) 0.2129(8) 0.103(4) Uani 1 1 d . . . . .
H23 H 1.0929 0.3572 0.1576 0.123 Uiso 1 1 calc R U . . .
C24 C 0.9809(12) 0.3037(7) 0.2537(6) 0.078(3) Uani 1 1 d . . . . .
H24 H 0.8939 0.3235 0.2271 0.094 Uiso 1 1 calc R U . . .
C25 C 0.9996(9) 0.2542(6) 0.3346(5) 0.055(2) Uani 1 1 d . . . . .
C26 C 1.2240(11) 0.1502(9) 0.5184(8) 0.094(4) Uani 1 1 d D . . . .
H26A H 1.3144 0.1532 0.4948 0.113 Uiso 1 1 calc R U . . .
H26B H 1.2349 0.0839 0.5541 0.113 Uiso 1 1 calc R U . . .
C27 C 1.1822(18) 0.2176(12) 0.5676(10) 0.168(8) Uani 1 1 d D . . . .
H27A H 1.1775 0.2831 0.5321 0.202 Uiso 1 1 calc R U . . .
H27B H 1.0884 0.2183 0.5873 0.202 Uiso 1 1 calc R U . . .
C28 C 1.281(3) 0.1904(18) 0.6392(12) 0.225(12) Uani 1 1 d . . . . .
H28A H 1.2466 0.2358 0.6668 0.338 Uiso 1 1 calc R U . . .
H28B H 1.3739 0.1921 0.6204 0.338 Uiso 1 1 calc R U . . .
H28C H 1.2857 0.1261 0.6754 0.338 Uiso 1 1 calc R U . . .
C29 C 0.3986(9) 0.3819(5) 0.9289(5) 0.0475(18) Uani 1 1 d . . . . .
C30 C 0.2642(9) 0.4529(6) 0.9068(6) 0.062(2) Uani 1 1 d . . . . .
H30 H 0.2185 0.4630 0.8592 0.075 Uiso 1 1 calc R U . . .
C31 C 0.2020(10) 0.5056(6) 0.9528(6) 0.068(3) Uani 1 1 d . . . . .
H31 H 0.1131 0.5500 0.9368 0.082 Uiso 1 1 calc R U . . .
C32 C 0.2666(9) 0.4962(6) 1.0248(5) 0.055(2) Uani 1 1 d . . . . .
C33 C 0.2008(11) 0.5557(6) 1.0704(6) 0.072(3) Uani 1 1 d . . . . .
H33 H 0.1118 0.5997 1.0541 0.086 Uiso 1 1 calc R U . . .
C34 C 0.2646(11) 0.5495(6) 1.1366(6) 0.073(3) Uani 1 1 d . . . . .
H34 H 0.2209 0.5902 1.1651 0.087 Uiso 1 1 calc R U . . .
C35 C 0.3971(10) 0.4821(6) 1.1630(5) 0.058(2) Uani 1 1 d . . . . .
H35 H 0.4413 0.4773 1.2092 0.070 Uiso 1 1 calc R U . . .
C36 C 0.4613(8) 0.4228(5) 1.1202(5) 0.0457(18) Uani 1 1 d . . . . .
H36 H 0.5496 0.3785 1.1380 0.055 Uiso 1 1 calc R U . . .
C37 C 0.3980(8) 0.4271(5) 1.0503(4) 0.0415(17) Uani 1 1 d . . . . .
C38 C 0.4635(7) 0.3661(4) 1.0029(4) 0.0366(15) Uani 1 1 d . . . . .
C39 C 0.5901(7) 0.2896(4) 1.0340(4) 0.0348(15) Uani 1 1 d . . . . .
H39 H 0.6249 0.2834 1.0835 0.042 Uiso 1 1 calc R U . . .
C40 C 0.7842(7) 0.1562(5) 1.0463(4) 0.0357(15) Uani 1 1 d . . . . .
C41 C 0.8730(8) 0.1847(5) 1.0836(4) 0.0447(17) Uani 1 1 d . . . . .
H41 H 0.8536 0.2499 1.0776 0.054 Uiso 1 1 calc R U . . .
C42 C 0.9884(8) 0.1177(6) 1.1291(4) 0.0474(18) Uani 1 1 d . . . . .
H42 H 1.0455 0.1372 1.1551 0.057 Uiso 1 1 calc R U . . .
C43 C 1.0205(8) 0.0214(6) 1.1367(5) 0.0486(19) Uani 1 1 d . . . . .
H43 H 1.0980 -0.0244 1.1685 0.058 Uiso 1 1 calc R U . . .
C44 C 0.9374(7) -0.0064(5) 1.0969(4) 0.0437(17) Uani 1 1 d . . . . .
H44 H 0.9605 -0.0712 1.1013 0.052 Uiso 1 1 calc R U . . .
C45 C 0.8196(7) 0.0599(5) 1.0503(4) 0.0390(16) Uani 1 1 d . . . . .
C46 C 0.7401(7) 0.0295(5) 1.0031(4) 0.0376(15) Uani 1 1 d . . . . .
C48 C 0.6641(8) -0.0657(5) 0.9583(5) 0.0437(17) Uani 1 1 d . . . . .
C49 C 0.6311(9) -0.1390(6) 0.9426(5) 0.053(2) Uani 1 1 d . . . . .
H49 H 0.6537 -0.2020 0.9798 0.064 Uiso 1 1 calc R U . . .
C50 C 0.5648(9) -0.1156(7) 0.8714(5) 0.059(2) Uani 1 1 d . . . . .
H50 H 0.5420 -0.1639 0.8598 0.071 Uiso 1 1 calc R U . . .
C51 C 0.5292(9) -0.0216(7) 0.8144(5) 0.058(2) Uani 1 1 d . . . . .
H51 H 0.4834 -0.0091 0.7662 0.069 Uiso 1 1 calc R U . . .
C52 C 0.5605(8) 0.0526(6) 0.8282(5) 0.0465(18) Uani 1 1 d . . . . .
H52 H 0.5373 0.1153 0.7903 0.056 Uiso 1 1 calc R U . . .
C53 C 0.6281(7) 0.0299(5) 0.9007(4) 0.0406(16) Uani 1 1 d . . . . .
C54 C 0.7568(8) -0.1442(5) 1.1000(5) 0.0459(17) Uani 1 1 d . . . . .
H54A H 0.6719 -0.1643 1.1143 0.055 Uiso 1 1 calc R U . . .
H54B H 0.7755 -0.1203 1.1407 0.055 Uiso 1 1 calc R U . . .
C55 C 0.8786(8) -0.2320(5) 1.1016(5) 0.0485(19) Uani 1 1 d . . . . .
H55A H 0.9655 -0.2142 1.0903 0.058 Uiso 1 1 calc R U . . .
H55B H 0.8625 -0.2566 1.0608 0.058 Uiso 1 1 calc R U . . .
C56 C 0.8903(11) -0.3101(7) 1.1850(6) 0.080(3) Uani 1 1 d . . . . .
H56A H 0.9671 -0.3664 1.1868 0.120 Uiso 1 1 calc R U . . .
H56B H 0.8040 -0.3275 1.1956 0.120 Uiso 1 1 calc R U . . .
H56C H 0.9071 -0.2855 1.2250 0.120 Uiso 1 1 calc R U . . .
N1 N 0.9072(7) 0.2212(4) 0.3940(4) 0.0475(15) Uani 1 1 d . . . . .
N2 N 1.1185(7) 0.1763(6) 0.4535(5) 0.065(2) Uani 1 1 d . . . . .
N3 N 0.6911(6) 0.2364(4) 0.5023(4) 0.0438(14) Uani 1 1 d . . . . .
N4 N 0.6619(6) 0.2281(4) 1.0017(3) 0.0370(13) Uani 1 1 d . . . . .
N5 N 0.6769(6) 0.0862(4) 0.9316(4) 0.0410(14) Uani 1 1 d . . . . .
N6 N 0.7308(6) -0.0647(4) 1.0223(3) 0.0385(13) Uani 1 1 d . . . . .
N10 N 0.6633(7) 0.1740(7) 0.2919(4) 0.065(2) Uani 1 1 d . . . . .
N20 N 0.7493(9) 0.2479(5) 0.7636(4) 0.0572(18) Uani 1 1 d . . . . .
O1 O 0.5144(6) 0.3426(5) 0.3682(3) 0.0631(16) Uani 1 1 d . . . . .
O2 O 0.4528(6) 0.3343(4) 0.8805(3) 0.0521(13) Uani 1 1 d . . . . .
O11 O 0.6935(6) 0.2539(5) 0.2768(3) 0.0617(15) Uani 1 1 d . . . . .
O12 O 0.6453(10) 0.1516(7) 0.2359(5) 0.114(3) Uani 1 1 d . . . . .
O13 O 0.6540(8) 0.1246(5) 0.3637(4) 0.0800(19) Uani 1 1 d . . . . .
O21 O 0.6243(7) 0.2529(4) 0.7798(3) 0.0598(15) Uani 1 1 d . . . . .
O22 O 0.7931(9) 0.2554(6) 0.6951(4) 0.096(2) Uani 1 1 d . . . . .
O23 O 0.8343(7) 0.2349(5) 0.8189(4) 0.0730(17) Uani 1 1 d . . . . .
Cu1 Cu 0.69903(10) 0.26092(7) 0.38805(6) 0.0496(3) Uani 1 1 d . . . . .
Cu2 Cu 0.61588(10) 0.22980(6) 0.89750(5) 0.0477(3) 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
C1 O1 1.311(9) . ?
C1 C2 1.412(11) . ?
C1 C10 1.416(11) . ?
C2 C3 1.339(13) . ?
C3 C4 1.392(13) . ?
C4 C9 1.421(11) . ?
C4 C5 1.421(13) . ?
C5 C6 1.360(15) . ?
C6 C7 1.382(15) . ?
C7 C8 1.387(12) . ?
C8 C9 1.388(12) . ?
C9 C10 1.482(10) . ?
C10 C11 1.400(10) . ?
C11 N3 1.322(9) . ?
C12 C13 1.385(11) . ?
C12 C17 1.407(10) . ?
C12 N3 1.421(9) . ?
C13 C14 1.384(12) . ?
C14 C15 1.369(12) . ?
C15 C16 1.355(12) . ?
C16 C17 1.391(11) . ?
C17 C18 1.453(11) . ?
C18 N1 1.316(10) . ?
C18 N2 1.390(9) . ?
C20 N2 1.381(12) . ?
C20 C25 1.390(12) . ?
C20 C21 1.394(13) . ?
C21 C22 1.387(17) . ?
C22 C23 1.312(18) . ?
C23 C24 1.410(15) . ?
C24 C25 1.362(13) . ?
C25 N1 1.402(10) . ?
C26 N2 1.479(13) . ?
C26 C27 1.529(15) . ?
C27 C28 1.523(19) . ?
C29 O2 1.305(9) . ?
C29 C38 1.416(10) . ?
C29 C30 1.425(11) . ?
C30 C31 1.342(13) . ?
C31 C32 1.415(13) . ?
C32 C37 1.397(11) . ?
C32 C33 1.416(12) . ?
C33 C34 1.337(14) . ?
C34 C35 1.399(13) . ?
C35 C36 1.372(10) . ?
C36 C37 1.406(11) . ?
C37 C38 1.457(10) . ?
C38 C39 1.423(9) . ?
C39 N4 1.285(8) . ?
C40 C41 1.391(10) . ?
C40 C45 1.393(10) . ?
C40 N4 1.430(8) . ?
C41 C42 1.367(10) . ?
C42 C43 1.378(11) . ?
C43 C44 1.370(10) . ?
C44 C45 1.388(9) . ?
C45 C46 1.466(9) . ?
C46 N5 1.331(9) . ?
C46 N6 1.396(9) . ?
C48 N6 1.364(9) . ?
C48 C49 1.385(10) . ?
C48 C53 1.417(10) . ?
C49 C50 1.350(11) . ?
C50 C51 1.395(12) . ?
C51 C52 1.374(11) . ?
C52 C53 1.378(10) . ?
C53 N5 1.385(9) . ?
C54 N6 1.460(9) . ?
C54 C55 1.512(10) . ?
C55 C56 1.525(12) . ?
N1 Cu1 1.973(6) . ?
N3 Cu1 1.926(6) . ?
N4 Cu2 1.927(6) . ?
N5 Cu2 1.980(6) . ?
N10 O12 1.202(9) . ?
N10 O13 1.244(9) . ?
N10 O11 1.285(10) . ?
N20 O22 1.238(9) . ?
N20 O21 1.240(9) . ?
N20 O23 1.266(9) . ?
O1 Cu1 1.862(5) . ?
O2 Cu2 1.862(5) . ?
O11 Cu1 2.021(6) . ?
O21 Cu2 1.990(6) . ?

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 C1 C2 118.8(8) . . ?
O1 C1 C10 122.2(7) . . ?
C2 C1 C10 119.0(7) . . ?
C3 C2 C1 121.6(9) . . ?
C2 C3 C4 122.7(9) . . ?
C3 C4 C9 119.6(8) . . ?
C3 C4 C5 122.0(9) . . ?
C9 C4 C5 118.4(9) . . ?
C6 C5 C4 120.6(10) . . ?
C5 C6 C7 121.2(9) . . ?
C6 C7 C8 119.3(10) . . ?
C7 C8 C9 121.6(9) . . ?
C8 C9 C4 118.8(7) . . ?
C8 C9 C10 123.3(7) . . ?
C4 C9 C10 117.8(8) . . ?
C11 C10 C1 122.9(6) . . ?
C11 C10 C9 117.8(7) . . ?
C1 C10 C9 119.0(7) . . ?
N3 C11 C10 126.4(7) . . ?
C13 C12 C17 119.2(7) . . ?
C13 C12 N3 120.3(7) . . ?
C17 C12 N3 120.3(7) . . ?
C14 C13 C12 120.9(8) . . ?
C15 C14 C13 120.1(8) . . ?
C16 C15 C14 119.3(8) . . ?
C15 C16 C17 123.1(8) . . ?
C16 C17 C12 117.5(7) . . ?
C16 C17 C18 122.4(7) . . ?
C12 C17 C18 120.0(7) . . ?
N1 C18 N2 110.5(7) . . ?
N1 C18 C17 125.0(7) . . ?
N2 C18 C17 124.2(7) . . ?
N2 C20 C25 107.8(7) . . ?
N2 C20 C21 129.8(10) . . ?
C25 C20 C21 122.4(10) . . ?
C22 C21 C20 115.2(11) . . ?
C23 C22 C21 122.4(11) . . ?
C22 C23 C24 123.4(12) . . ?
C25 C24 C23 115.8(12) . . ?
C24 C25 C20 120.7(8) . . ?
C24 C25 N1 132.3(9) . . ?
C20 C25 N1 107.0(7) . . ?
N2 C26 C27 112.4(9) . . ?
C28 C27 C26 115.1(15) . . ?
O2 C29 C38 124.2(7) . . ?
O2 C29 C30 118.0(7) . . ?
C38 C29 C30 117.8(7) . . ?
C31 C30 C29 121.6(8) . . ?
C30 C31 C32 122.4(8) . . ?
C37 C32 C31 118.7(8) . . ?
C37 C32 C33 120.2(9) . . ?
C31 C32 C33 121.1(9) . . ?
C34 C33 C32 121.0(9) . . ?
C33 C34 C35 120.1(8) . . ?
C36 C35 C34 119.5(9) . . ?
C35 C36 C37 122.2(8) . . ?
C32 C37 C36 116.9(7) . . ?
C32 C37 C38 119.4(7) . . ?
C36 C37 C38 123.7(6) . . ?
C29 C38 C39 121.7(6) . . ?
C29 C38 C37 119.8(6) . . ?
C39 C38 C37 118.5(6) . . ?
N4 C39 C38 127.5(6) . . ?
C41 C40 C45 119.5(6) . . ?
C41 C40 N4 118.7(6) . . ?
C45 C40 N4 121.7(6) . . ?
C42 C41 C40 120.5(7) . . ?
C41 C42 C43 120.3(7) . . ?
C44 C43 C42 119.5(7) . . ?
C43 C44 C45 121.6(7) . . ?
C44 C45 C40 118.4(6) . . ?
C44 C45 C46 120.1(6) . . ?
C40 C45 C46 121.4(6) . . ?
N5 C46 N6 110.2(6) . . ?
N5 C46 C45 124.2(6) . . ?
N6 C46 C45 125.3(6) . . ?
N6 C48 C49 132.5(7) . . ?
N6 C48 C53 107.4(6) . . ?
C49 C48 C53 120.1(7) . . ?
C50 C49 C48 117.6(8) . . ?
C49 C50 C51 122.6(8) . . ?
C52 C51 C50 121.2(8) . . ?
C51 C52 C53 116.9(8) . . ?
C52 C53 N5 131.1(7) . . ?
C52 C53 C48 121.6(6) . . ?
N5 C53 C48 107.3(6) . . ?
N6 C54 C55 114.3(6) . . ?
C54 C55 C56 108.6(7) . . ?
C18 N1 C25 108.1(7) . . ?
C18 N1 Cu1 122.0(5) . . ?
C25 N1 Cu1 128.3(6) . . ?
C20 N2 C18 106.5(7) . . ?
C20 N2 C26 125.7(8) . . ?
C18 N2 C26 126.7(8) . . ?
C11 N3 C12 117.5(6) . . ?
C11 N3 Cu1 123.1(5) . . ?
C12 N3 Cu1 119.2(4) . . ?
C39 N4 C40 116.7(6) . . ?
C39 N4 Cu2 123.9(5) . . ?
C40 N4 Cu2 119.4(4) . . ?
C46 N5 C53 108.1(6) . . ?
C46 N5 Cu2 122.3(4) . . ?
C53 N5 Cu2 127.1(5) . . ?
C48 N6 C46 107.0(6) . . ?
C48 N6 C54 122.8(6) . . ?
C46 N6 C54 129.0(6) . . ?
O12 N10 O13 124.0(10) . . ?
O12 N10 O11 118.1(9) . . ?
O13 N10 O11 117.9(7) . . ?
O22 N20 O21 122.0(8) . . ?
O22 N20 O23 119.2(9) . . ?
O21 N20 O23 118.8(7) . . ?
C1 O1 Cu1 128.7(5) . . ?
C29 O2 Cu2 127.9(5) . . ?
N10 O11 Cu1 102.1(4) . . ?
N20 O21 Cu2 104.9(5) . . ?
O1 Cu1 N3 93.1(2) . . ?
O1 Cu1 N1 158.9(3) . . ?
N3 Cu1 N1 91.2(3) . . ?
O1 Cu1 O11 88.4(2) . . ?
N3 Cu1 O11 165.0(3) . . ?
N1 Cu1 O11 92.8(3) . . ?
O2 Cu2 N4 94.6(2) . . ?
O2 Cu2 N5 140.8(2) . . ?
N4 Cu2 N5 93.1(2) . . ?
O2 Cu2 O21 90.6(2) . . ?
N4 Cu2 O21 159.5(3) . . ?
N5 Cu2 O21 95.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C24 H24 O11 0.93 2.50 3.137(13) 125.9 .
C52 H52 O21 0.93 2.46 3.141(10) 129.7 .
C11 H11 O22 0.93 2.59 3.371(11) 141.4 .
C24 H24 O11 0.93 2.50 3.137(13) 125.9 .
C52 H52 O21 0.93 2.46 3.141(10) 129.7 .
C55 H55A O23 0.97 2.53 3.259(10) 132.1 2_757
C11 H11 O22 0.93 2.59 3.371(11) 141.4 .
C24 H24 O11 0.93 2.50 3.137(13) 125.9 .
C52 H52 O21 0.93 2.46 3.141(10) 129.7 .
C55 H55A O23 0.97 2.53 3.259(10) 132.1 2_757

_refine_diff_density_max         3.191
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.144

_shelxl_version_number           2013-4

