# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 887474'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H32 Cu2 N6 O4, 2(Cl O4)'
_chemical_formula_sum            'C44 H32 Cl2 Cu2 N6 O12'
_chemical_formula_weight         1034.73

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'
Cl Cl 0.1484 0.1585 '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      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                   24.267(3)
_cell_length_b                   16.0881(19)
_cell_length_c                   12.0926(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.822(3)
_cell_angle_gamma                90
_cell_volume                     4249.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3510
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      31.06

_exptl_crystal_description       prism
_exptl_crystal_colour            light-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             2104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    1.200
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_T_max  0.9337
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            19077
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             19077
_reflns_number_gt                11115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0152P)²+18.7043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         19077
_refine_ls_number_parameters     336
_refine_ls_number_restraints     385
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2077
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.029
_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
Cu1 Cu 0.53371(4) 0.38660(6) 0.62025(9) 0.0399(3) Uani 1 1 d . U . . .
O1 O 0.5584(2) 0.4944(3) 0.6904(5) 0.0463(14) Uani 1 1 d . U . . .
O2 O 0.5137(2) 0.4174(3) 0.4332(5) 0.0412(13) Uani 1 1 d . U . . .
N1 N 0.5268(3) 0.2664(4) 0.6177(6) 0.0452(16) Uani 1 1 d . U . . .
C2 C 0.5764(4) 0.2201(6) 0.6414(8) 0.057(2) Uani 1 1 d . U . . .
C3 C 0.5724(5) 0.1346(6) 0.6383(9) 0.077(3) Uani 1 1 d . U . . .
H3 H 0.6066 0.1016 0.6556 0.092 Uiso 1 1 calc R U . . .
C4 C 0.5158(6) 0.0995(6) 0.6089(10) 0.088(3) Uani 1 1 d . U . . .
H4 H 0.5120 0.0419 0.6059 0.106 Uiso 1 1 calc R U . . .
C5 C 0.4654(5) 0.1471(6) 0.5841(9) 0.072(3) Uani 1 1 d . U . . .
H5 H 0.4276 0.1227 0.5643 0.087 Uiso 1 1 calc R U . . .
C6 C 0.4719(4) 0.2323(5) 0.5889(7) 0.052(2) Uani 1 1 d . U . . .
N7 N 0.6228(3) 0.3527(4) 0.6719(6) 0.0494(18) Uani 1 1 d . U . . .
C8 C 0.6320(4) 0.2693(6) 0.6729(7) 0.054(2) Uani 1 1 d . U . . .
C9 C 0.6897(5) 0.2378(7) 0.7051(9) 0.071(3) Uani 1 1 d . U . . .
H9 H 0.6961 0.1807 0.7068 0.085 Uiso 1 1 calc R U . . .
C10 C 0.7376(5) 0.2919(8) 0.7346(9) 0.079(3) Uani 1 1 d . U . . .
H10 H 0.7769 0.2713 0.7575 0.095 Uiso 1 1 calc R U . . .
C11 C 0.7285(4) 0.3752(7) 0.7308(9) 0.073(3) Uani 1 1 d . U . . .
H11 H 0.7608 0.4120 0.7484 0.088 Uiso 1 1 calc R U . . .
C12 C 0.6699(4) 0.4042(6) 0.7001(8) 0.060(2) Uani 1 1 d . U . . .
H12 H 0.6633 0.4612 0.6992 0.072 Uiso 1 1 calc R U . . .
N13 N 0.4425(3) 0.3737(4) 0.5778(6) 0.0418(16) Uani 1 1 d . U . . .
C14 C 0.4234(4) 0.2936(5) 0.5645(7) 0.047(2) Uani 1 1 d . U . . .
C15 C 0.3623(4) 0.2740(6) 0.5276(8) 0.061(2) Uani 1 1 d . U . . .
H15 H 0.3499 0.2188 0.5209 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3207(4) 0.3364(6) 0.5013(8) 0.062(2) Uani 1 1 d . U . . .
H16 H 0.2794 0.3243 0.4756 0.074 Uiso 1 1 calc R U . . .
C17 C 0.3402(4) 0.4175(6) 0.5131(8) 0.054(2) Uani 1 1 d . U . . .
H17 H 0.3124 0.4611 0.4953 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4010(4) 0.4331(5) 0.5512(7) 0.044(2) Uani 1 1 d . U . . .
H18 H 0.4139 0.4881 0.5588 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5756(3) 0.6372(4) 0.7281(7) 0.0367(17) Uani 1 1 d . U . . .
C20 C 0.6334(4) 0.6244(5) 0.8212(7) 0.048(2) Uani 1 1 d . U . . .
H20 H 0.6494 0.5708 0.8362 0.057 Uiso 1 1 calc R U . . .
C21 C 0.6682(4) 0.6886(5) 0.8923(8) 0.060(2) Uani 1 1 d . U . . .
H21 H 0.7069 0.6785 0.9554 0.072 Uiso 1 1 calc R U . . .
C22 C 0.6453(4) 0.7673(6) 0.8693(9) 0.065(3) Uani 1 1 d . U . . .
H22 H 0.6684 0.8112 0.9171 0.078 Uiso 1 1 calc R U . . .
C23 C 0.5889(4) 0.7820(5) 0.7765(9) 0.060(2) Uani 1 1 d . U . . .
H23 H 0.5739 0.8361 0.7608 0.072 Uiso 1 1 calc R U . . .
C24 C 0.5535(4) 0.7176(5) 0.7055(8) 0.050(2) Uani 1 1 d . U . . .
H24 H 0.5149 0.7283 0.6426 0.060 Uiso 1 1 calc R U . . .
C25 C 0.5365(4) 0.5663(5) 0.6551(6) 0.0340(18) Uani 1 1 d . U . . .
Cl1 Cl 0.17293(12) 0.49632(16) 0.4487(3) 0.0801(9) Uani 1 1 d D U . . .
O3 O 0.1821(11) 0.4126(9) 0.474(2) 0.102(8) Uani 0.590(16) 1 d D U P A 1
O4 O 0.1136(6) 0.5197(8) 0.430(2) 0.108(6) Uani 0.590(16) 1 d D U P A 1
O5 O 0.2150(8) 0.5428(11) 0.548(2) 0.143(8) Uani 0.590(16) 1 d D U P A 1
O6 O 0.1798(11) 0.5174(11) 0.3437(18) 0.154(7) Uani 0.590(16) 1 d D U P A 1
O3B O 0.1883(18) 0.4130(17) 0.432(4) 0.102(9) Uani 0.410(16) 1 d . U P A 2
O4B O 0.1289(14) 0.5199(13) 0.333(3) 0.135(9) Uani 0.410(16) 1 d . U P A 2
O5B O 0.2238(10) 0.5435(14) 0.478(3) 0.088(7) Uani 0.410(16) 1 d . U P A 2
O6B O 0.1475(14) 0.4949(19) 0.527(3) 0.146(8) Uani 0.410(16) 1 d . U P A 2


_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 1.910(5) . ?
Cu1 N1 1.940(6) . ?
Cu1 N7 2.046(7) . ?
Cu1 N13 2.054(6) . ?
Cu1 O2 2.154(5) . ?
O1 C25 1.267(8) . ?
O2 C25 1.250(8) 5_666 ?
N1 C2 1.337(10) . ?
N1 C6 1.340(10) . ?
C2 C3 1.378(12) . ?
C2 C8 1.464(12) . ?
C3 C4 1.379(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(12) . ?
C5 H5 0.9300 . ?
C6 C14 1.465(11) . ?
N7 C12 1.330(10) . ?
N7 C8 1.359(10) . ?
C8 C9 1.377(12) . ?
C9 C10 1.369(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(12) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N13 C18 1.322(10) . ?
N13 C14 1.355(9) . ?
C14 C15 1.385(11) . ?
C15 C16 1.360(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.379(10) . ?
C19 C24 1.381(10) . ?
C19 C25 1.500(10) . ?
C20 C21 1.374(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(11) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 O2 1.250(8) 5_666 ?
Cl1 O6B 1.34(3) . ?
Cl1 O5B 1.357(19) . ?
Cl1 O3 1.378(14) . ?
Cl1 O4B 1.39(2) . ?
Cl1 O6 1.392(13) . ?
Cl1 O5 1.404(14) . ?
Cl1 O4 1.407(12) . ?
Cl1 O3B 1.43(3) . ?

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 N1 157.1(2) . . ?
O1 Cu1 N7 91.2(2) . . ?
N1 Cu1 N7 79.1(3) . . ?
O1 Cu1 N13 107.3(2) . . ?
N1 Cu1 N13 79.6(3) . . ?
N7 Cu1 N13 158.5(3) . . ?
O1 Cu1 O2 98.1(2) . . ?
N1 Cu1 O2 103.5(2) . . ?
N7 Cu1 O2 96.1(2) . . ?
N13 Cu1 O2 92.1(2) . . ?
C25 O1 Cu1 132.5(5) . . ?
C25 O2 Cu1 129.4(4) 5_666 . ?
C2 N1 C6 121.9(7) . . ?
C2 N1 Cu1 119.2(6) . . ?
C6 N1 Cu1 118.8(6) . . ?
N1 C2 C3 120.2(9) . . ?
N1 C2 C8 113.3(8) . . ?
C3 C2 C8 126.4(9) . . ?
C2 C3 C4 117.8(10) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 121.6(10) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.5(10) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 120.0(8) . . ?
N1 C6 C14 113.4(7) . . ?
C5 C6 C14 126.6(8) . . ?
C12 N7 C8 119.6(8) . . ?
C12 N7 Cu1 126.0(6) . . ?
C8 N7 Cu1 114.4(6) . . ?
N7 C8 C9 120.6(9) . . ?
N7 C8 C2 113.8(7) . . ?
C9 C8 C2 125.6(9) . . ?
C10 C9 C8 118.9(10) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 120.8(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 118.5(10) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N7 C12 C11 121.7(9) . . ?
N7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C18 N13 C14 118.2(7) . . ?
C18 N13 Cu1 127.7(5) . . ?
C14 N13 Cu1 113.7(5) . . ?
N13 C14 C15 121.2(8) . . ?
N13 C14 C6 114.4(7) . . ?
C15 C14 C6 124.4(8) . . ?
C16 C15 C14 119.3(8) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 119.3(8) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 118.9(8) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
N13 C18 C17 123.1(8) . . ?
N13 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C20 C19 C24 118.0(7) . . ?
C20 C19 C25 121.7(7) . . ?
C24 C19 C25 120.2(7) . . ?
C21 C20 C19 121.9(8) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C22 C21 C20 119.1(9) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 C21 120.3(8) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.8(8) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 119.8(8) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
O2 C25 O1 126.1(7) 5_666 . ?
O2 C25 C19 118.4(7) 5_666 . ?
O1 C25 C19 115.5(7) . . ?
O6B Cl1 O5B 117.9(16) . . ?
O6B Cl1 O4B 109.0(19) . . ?
O5B Cl1 O4B 109.0(17) . . ?
O3 Cl1 O6 111.7(10) . . ?
O3 Cl1 O5 110.0(10) . . ?
O6 Cl1 O5 108.5(13) . . ?
O3 Cl1 O4 110.6(9) . . ?
O6 Cl1 O4 107.8(9) . . ?
O5 Cl1 O4 108.0(9) . . ?
O6B Cl1 O3B 108.4(19) . . ?
O5B Cl1 O3B 107.4(17) . . ?
O4B Cl1 O3B 104.2(19) . . ?

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 N1 C2 C3 -0.8(13) . . . . ?
Cu1 N1 C2 C3 -179.1(7) . . . . ?
C6 N1 C2 C8 -179.0(7) . . . . ?
Cu1 N1 C2 C8 2.8(10) . . . . ?
N1 C2 C3 C4 0.7(14) . . . . ?
C8 C2 C3 C4 178.7(9) . . . . ?
C2 C3 C4 C5 -0.3(17) . . . . ?
C3 C4 C5 C6 0.0(17) . . . . ?
C2 N1 C6 C5 0.5(13) . . . . ?
Cu1 N1 C6 C5 178.7(7) . . . . ?
C2 N1 C6 C14 -179.2(7) . . . . ?
Cu1 N1 C6 C14 -0.9(9) . . . . ?
C4 C5 C6 N1 -0.1(14) . . . . ?
C4 C5 C6 C14 179.5(9) . . . . ?
C12 N7 C8 C9 1.2(12) . . . . ?
Cu1 N7 C8 C9 179.6(7) . . . . ?
C12 N7 C8 C2 179.3(7) . . . . ?
Cu1 N7 C8 C2 -2.3(9) . . . . ?
N1 C2 C8 N7 -0.1(11) . . . . ?
C3 C2 C8 N7 -178.2(9) . . . . ?
N1 C2 C8 C9 177.9(8) . . . . ?
C3 C2 C8 C9 -0.2(15) . . . . ?
N7 C8 C9 C10 -0.8(14) . . . . ?
C2 C8 C9 C10 -178.7(9) . . . . ?
C8 C9 C10 C11 -0.8(16) . . . . ?
C9 C10 C11 C12 2.0(16) . . . . ?
C8 N7 C12 C11 0.0(13) . . . . ?
Cu1 N7 C12 C11 -178.2(7) . . . . ?
C10 C11 C12 N7 -1.6(15) . . . . ?
C18 N13 C14 C15 -1.9(11) . . . . ?
Cu1 N13 C14 C15 -175.5(6) . . . . ?
C18 N13 C14 C6 176.5(7) . . . . ?
Cu1 N13 C14 C6 2.9(8) . . . . ?
N1 C6 C14 N13 -1.4(10) . . . . ?
C5 C6 C14 N13 179.0(8) . . . . ?
N1 C6 C14 C15 177.0(8) . . . . ?
C5 C6 C14 C15 -2.7(14) . . . . ?
N13 C14 C15 C16 1.7(13) . . . . ?
C6 C14 C15 C16 -176.5(8) . . . . ?
C14 C15 C16 C17 -0.7(14) . . . . ?
C15 C16 C17 C18 -0.1(14) . . . . ?
C14 N13 C18 C17 1.1(12) . . . . ?
Cu1 N13 C18 C17 173.7(6) . . . . ?
C16 C17 C18 N13 -0.1(13) . . . . ?
C24 C19 C20 C21 1.6(12) . . . . ?
C25 C19 C20 C21 -176.6(8) . . . . ?
C19 C20 C21 C22 -1.0(14) . . . . ?
C20 C21 C22 C23 -0.3(15) . . . . ?
C21 C22 C23 C24 0.9(15) . . . . ?
C22 C23 C24 C19 -0.3(13) . . . . ?
C20 C19 C24 C23 -0.9(12) . . . . ?
C25 C19 C24 C23 177.3(7) . . . . ?
Cu1 O1 C25 O2 9.4(11) . . . 5_666 ?
Cu1 O1 C25 C19 -170.7(5) . . . . ?
C20 C19 C25 O2 -175.3(7) . . . 5_666 ?
C24 C19 C25 O2 6.5(10) . . . 5_666 ?
C20 C19 C25 O1 4.8(10) . . . . ?
C24 C19 C25 O1 -173.4(7) . . . . ?

_refine_diff_density_max         1.511
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_020vmj06
_database_code_depnum_ccdc_archive 'CCDC 887476'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H22 Cu2 F4 N6 O4, 2(Cl O4)'
_chemical_formula_sum            'C38 H22 Cl2 Cu2 F4 N6 O12'
_chemical_formula_weight         1028.60

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.7752(8)
_cell_length_b                   24.8336(15)
_cell_length_c                   13.2397(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.343(1)
_cell_angle_gamma                90.00
_cell_volume                     3856.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    8153
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.92

_exptl_crystal_description       Prism
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      No
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    1.336
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_T_max  0.9097
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX AXS CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.61
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31343
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6781
_reflns_number_gt                4203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625'
_computing_cell_refinement       'SMART V 5.625'
_computing_data_reduction        'SAINTPLUS V 7.01A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL V 6.10'
_computing_publication_material  'SHELXTL V 6.10'
_solved_by                       SimonHO

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6781
_refine_ls_number_parameters     614
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.856
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.26022(4) 0.076889(17) 0.98116(3) 0.04572(14) Uani 1 1 d . . .
Cu2 Cu 0.62501(4) -0.066182(17) 0.57783(3) 0.04298(14) Uani 1 1 d . . .
F1 F 0.46395(17) 0.01588(8) 0.78366(16) 0.0554(6) Uani 1 1 d . . .
F2 F 0.69247(19) 0.13507(8) 0.68668(18) 0.0728(7) Uani 1 1 d . . .
F3 F 0.6966(2) 0.20382(9) 0.8457(2) 0.0850(8) Uani 1 1 d . . .
F4 F 0.58097(19) 0.17914(8) 0.97165(18) 0.0736(7) Uani 1 1 d . . .
O1 O 0.4942(2) 0.07774(11) 1.0447(2) 0.0692(8) Uani 1 1 d . . .
O2 O 0.3413(2) 0.08642(10) 0.88883(19) 0.0501(7) Uani 1 1 d . . .
O3 O 0.62501(18) -0.01158(9) 0.68081(16) 0.0401(6) Uani 1 1 d . . .
O4 O 0.55055(19) 0.05118(9) 0.55054(18) 0.0441(6) Uani 1 1 d . . .
N1 N 0.2729(2) 0.15230(12) 1.0431(2) 0.0467(8) Uani 1 1 d . . .
N2 N 0.1925(2) 0.06523(13) 1.0855(2) 0.0427(7) Uani 1 1 d . . .
N3 N 0.2314(2) -0.00320(12) 0.9621(2) 0.0480(8) Uani 1 1 d . . .
N4 N 0.5480(2) -0.12219(11) 0.6366(2) 0.0456(8) Uani 1 1 d . . .
N5 N 0.6454(3) -0.12913(12) 0.5020(2) 0.0491(8) Uani 1 1 d . . .
N6 N 0.7249(2) -0.03457(14) 0.5045(2) 0.0504(8) Uani 1 1 d . . .
C1 C 0.5182(3) 0.09676(14) 0.8794(3) 0.0386(9) Uani 1 1 d . . .
C2 C 0.5223(3) 0.06297(14) 0.7999(3) 0.0381(8) Uani 1 1 d . . .
C3 C 0.5801(3) 0.07300(13) 0.7333(3) 0.0355(8) Uani 1 1 d . . .
C4 C 0.6348(3) 0.12214(14) 0.7485(3) 0.0444(9) Uani 1 1 d . . .
C5 C 0.6357(3) 0.15723(15) 0.8285(3) 0.0517(10) Uani 1 1 d . . .
C6 C 0.5786(3) 0.14434(15) 0.8937(3) 0.0469(10) Uani 1 1 d . . .
C7 C 0.4488(4) 0.08536(14) 0.9464(3) 0.0450(9) Uani 1 1 d . . .
C8 C 0.5836(3) 0.03479(14) 0.6453(3) 0.0358(8) Uani 1 1 d . . .
C9 C 0.3201(3) 0.19525(16) 1.0176(3) 0.0578(11) Uani 1 1 d . . .
H9 H 0.3483 0.1921 0.9630 0.069 Uiso 1 1 calc R . .
C10 C 0.3286(3) 0.24398(16) 1.0691(4) 0.0630(12) Uani 1 1 d . . .
H10 H 0.3629 0.2732 1.0504 0.076 Uiso 1 1 calc R . .
C11 C 0.2860(4) 0.24882(17) 1.1478(4) 0.0679(12) Uani 1 1 d . . .
H11 H 0.2917 0.2814 1.1842 0.082 Uiso 1 1 calc R . .
C12 C 0.2345(3) 0.20548(17) 1.1735(3) 0.0608(11) Uani 1 1 d . . .
H12 H 0.2028 0.2088 1.2255 0.073 Uiso 1 1 calc R . .
C13 C 0.2305(3) 0.15727(16) 1.1219(3) 0.0465(10) Uani 1 1 d . . .
C14 C 0.1831(3) 0.10668(17) 1.1452(3) 0.0472(10) Uani 1 1 d . . .
C15 C 0.1329(3) 0.09994(19) 1.2202(3) 0.0595(11) Uani 1 1 d . . .
H15 H 0.1255 0.1286 1.2622 0.071 Uiso 1 1 calc R . .
C16 C 0.0943(3) 0.0488(2) 1.2299(3) 0.0663(13) Uani 1 1 d . . .
H16 H 0.0600 0.0431 1.2792 0.080 Uiso 1 1 calc R . .
C17 C 0.1057(3) 0.00659(19) 1.1685(3) 0.0621(12) Uani 1 1 d . . .
H17 H 0.0797 -0.0276 1.1758 0.074 Uiso 1 1 calc R . .
C18 C 0.1566(3) 0.01582(17) 1.0957(3) 0.0500(10) Uani 1 1 d . . .
C19 C 0.1765(3) -0.02374(16) 1.0221(3) 0.0507(10) Uani 1 1 d . . .
C20 C 0.1411(3) -0.07665(18) 1.0105(4) 0.0691(13) Uani 1 1 d . . .
H20 H 0.1047 -0.0907 1.0531 0.083 Uiso 1 1 calc R . .
C21 C 0.1606(4) -0.10790(19) 0.9349(5) 0.0822(15) Uani 1 1 d . . .
H21 H 0.1351 -0.1434 0.9245 0.099 Uiso 1 1 calc R . .
C22 C 0.2167(4) -0.08802(19) 0.8744(4) 0.0767(14) Uani 1 1 d . . .
H22 H 0.2310 -0.1095 0.8236 0.092 Uiso 1 1 calc R . .
C23 C 0.2518(3) -0.03486(17) 0.8910(3) 0.0598(11) Uani 1 1 d . . .
H23 H 0.2911 -0.0208 0.8511 0.072 Uiso 1 1 calc R . .
C24 C 0.5006(3) -0.11455(15) 0.7083(3) 0.0535(10) Uani 1 1 d . . .
H24 H 0.5111 -0.0815 0.7442 0.064 Uiso 1 1 calc R . .
C25 C 0.4367(4) -0.15313(18) 0.7320(4) 0.0720(13) Uani 1 1 d . . .
H25 H 0.4043 -0.1465 0.7826 0.086 Uiso 1 1 calc R . .
C26 C 0.4221(4) -0.20161(19) 0.6789(4) 0.0856(15) Uani 1 1 d . . .
H26 H 0.3789 -0.2285 0.6929 0.103 Uiso 1 1 calc R . .
C27 C 0.4709(4) -0.21054(17) 0.6053(4) 0.0732(13) Uani 1 1 d . . .
H27 H 0.4614 -0.2435 0.5692 0.088 Uiso 1 1 calc R . .
C28 C 0.5342(3) -0.17031(16) 0.5851(3) 0.0530(10) Uani 1 1 d . . .
C29 C 0.5929(3) -0.17458(17) 0.5096(3) 0.0560(11) Uani 1 1 d . . .
C30 C 0.5966(4) -0.21895(18) 0.4479(4) 0.0833(14) Uani 1 1 d . . .
H30 H 0.5603 -0.2509 0.4517 0.100 Uiso 1 1 calc R . .
C31 C 0.6552(5) -0.2145(2) 0.3809(5) 0.1028(19) Uani 1 1 d . . .
H31 H 0.6582 -0.2440 0.3387 0.123 Uiso 1 1 calc R . .
C32 C 0.7098(4) -0.1676(2) 0.3745(4) 0.0844(15) Uani 1 1 d . . .
H32 H 0.7501 -0.1652 0.3296 0.101 Uiso 1 1 calc R . .
C33 C 0.7029(3) -0.12407(18) 0.4371(3) 0.0566(11) Uani 1 1 d . . .
C34 C 0.7514(3) -0.07015(19) 0.4407(3) 0.0557(11) Uani 1 1 d . . .
C35 C 0.8183(4) -0.0560(2) 0.3849(3) 0.0744(14) Uani 1 1 d . . .
H35 H 0.8352 -0.0809 0.3412 0.089 Uiso 1 1 calc R . .
C36 C 0.8595(4) -0.0041(3) 0.3952(4) 0.0872(16) Uani 1 1 d . . .
H36 H 0.9045 0.0064 0.3581 0.105 Uiso 1 1 calc R . .
C37 C 0.8341(3) 0.0318(2) 0.4600(4) 0.0738(13) Uani 1 1 d . . .
H37 H 0.8620 0.0668 0.4679 0.089 Uiso 1 1 calc R . .
C38 C 0.7665(3) 0.01554(18) 0.5138(3) 0.0602(11) Uani 1 1 d . . .
H38 H 0.7492 0.0401 0.5579 0.072 Uiso 1 1 calc R . .
Cl1 Cl 0.02380(9) 0.13392(4) 0.78624(9) 0.0561(3) Uani 1 1 d . . .
O5 O 0.0832(2) 0.08402(10) 0.8273(2) 0.0680(8) Uani 1 1 d . . .
O6 O -0.0095(3) 0.15593(12) 0.8675(3) 0.1000(11) Uani 1 1 d . . .
O7 O 0.0985(3) 0.16971(11) 0.7657(3) 0.0883(10) Uani 1 1 d . . .
O8 O -0.0723(3) 0.12271(13) 0.6898(3) 0.1103(12) Uani 1 1 d . . .
Cl2 Cl 0.47276(11) 0.32348(5) 0.87083(11) 0.0793(4) Uani 1 1 d DU . .
O9 O 0.5066(7) 0.3026(2) 0.7878(7) 0.1149(18) Uani 0.735(10) 1 d PDU A 1
O10 O 0.3529(4) 0.3177(3) 0.8216(5) 0.1197(18) Uani 0.735(10) 1 d PDU A 1
O11 O 0.5023(6) 0.37938(17) 0.8856(6) 0.0944(17) Uani 0.735(10) 1 d PDU A 1
O12 O 0.5229(7) 0.2954(3) 0.9715(5) 0.133(2) Uani 0.735(10) 1 d PDU A 1
O9A O 0.5684(13) 0.3034(6) 0.8541(17) 0.094(3) Uani 0.265(10) 1 d PDU A 2
O10A O 0.3792(12) 0.2885(7) 0.8464(16) 0.112(3) Uani 0.265(10) 1 d PDU A 2
O11A O 0.4528(17) 0.3795(3) 0.8518(18) 0.098(3) Uani 0.265(10) 1 d PDU A 2
O12A O 0.5089(17) 0.3206(8) 0.9882(7) 0.110(3) Uani 0.265(10) 1 d PDU A 2


_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 O2 1.904(2) . ?
Cu1 N2 1.920(3) . ?
Cu1 N3 2.020(3) . ?
Cu1 N1 2.025(3) . ?
Cu1 O5 2.376(3) . ?
Cu2 O3 1.923(2) . ?
Cu2 N5 1.930(3) . ?
Cu2 N4 2.029(3) . ?
Cu2 N6 2.042(3) . ?
Cu2 O4 2.244(2) 3_656 ?
F1 C2 1.358(3) . ?
F2 C4 1.340(4) . ?
F3 C5 1.362(4) . ?
F4 C6 1.337(4) . ?
O1 C7 1.212(4) . ?
O2 C7 1.280(4) . ?
O3 C8 1.276(4) . ?
O4 C8 1.224(4) . ?
O4 Cu2 2.244(2) 3_656 ?
N1 C9 1.333(4) . ?
N1 C13 1.358(4) . ?
N2 C14 1.331(4) . ?
N2 C18 1.336(4) . ?
N3 C23 1.329(4) . ?
N3 C19 1.351(4) . ?
N4 C24 1.326(4) . ?
N4 C28 1.353(4) . ?
N5 C29 1.337(5) . ?
N5 C33 1.339(4) . ?
N6 C38 1.340(4) . ?
N6 C34 1.355(4) . ?
C1 C2 1.363(4) . ?
C1 C6 1.383(5) . ?
C1 C7 1.508(5) . ?
C2 C3 1.379(4) . ?
C3 C4 1.381(4) . ?
C3 C8 1.516(4) . ?
C4 C5 1.368(5) . ?
C5 C6 1.371(5) . ?
C9 C10 1.372(5) . ?
C10 C11 1.360(5) . ?
C11 C12 1.373(5) . ?
C12 C13 1.370(5) . ?
C13 C14 1.479(5) . ?
C14 C15 1.390(5) . ?
C15 C16 1.386(5) . ?
C16 C17 1.370(5) . ?
C17 C18 1.379(5) . ?
C18 C19 1.475(5) . ?
C19 C20 1.378(5) . ?
C20 C21 1.365(6) . ?
C21 C22 1.362(6) . ?
C22 C23 1.384(5) . ?
C24 C25 1.373(5) . ?
C25 C26 1.369(5) . ?
C26 C27 1.367(6) . ?
C27 C28 1.377(5) . ?
C28 C29 1.473(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.374(6) . ?
C31 C32 1.378(6) . ?
C32 C33 1.386(5) . ?
C33 C34 1.468(5) . ?
C34 C35 1.378(5) . ?
C35 C36 1.378(6) . ?
C36 C37 1.362(6) . ?
C37 C38 1.380(5) . ?
Cl1 O8 1.404(3) . ?
Cl1 O7 1.407(3) . ?
Cl1 O6 1.414(3) . ?
Cl1 O5 1.442(2) . ?
Cl2 O10A 1.407(7) . ?
Cl2 O10 1.414(4) . ?
Cl2 O12 1.414(4) . ?
Cl2 O9A 1.416(7) . ?
Cl2 O11A 1.418(8) . ?
Cl2 O9 1.429(4) . ?
Cl2 O11 1.432(4) . ?
Cl2 O12A 1.437(8) . ?

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 Cu1 N2 174.36(11) . . ?
O2 Cu1 N3 99.25(12) . . ?
N2 Cu1 N3 80.20(13) . . ?
O2 Cu1 N1 99.70(11) . . ?
N2 Cu1 N1 80.48(13) . . ?
N3 Cu1 N1 160.46(13) . . ?
O2 Cu1 O5 90.90(10) . . ?
N2 Cu1 O5 94.62(10) . . ?
N3 Cu1 O5 84.36(10) . . ?
N1 Cu1 O5 100.06(10) . . ?
O3 Cu2 N5 167.86(11) . . ?
O3 Cu2 N4 94.30(11) . . ?
N5 Cu2 N4 80.24(14) . . ?
O3 Cu2 N6 103.99(11) . . ?
N5 Cu2 N6 79.94(14) . . ?
N4 Cu2 N6 159.33(13) . . ?
O3 Cu2 O4 97.99(9) . 3_656 ?
N5 Cu2 O4 92.36(10) . 3_656 ?
N4 Cu2 O4 85.02(10) . 3_656 ?
N6 Cu2 O4 101.60(10) . 3_656 ?
C7 O2 Cu1 110.1(2) . . ?
C8 O3 Cu2 119.5(2) . . ?
C8 O4 Cu2 131.8(2) . 3_656 ?
C9 N1 C13 118.7(3) . . ?
C9 N1 Cu1 127.5(3) . . ?
C13 N1 Cu1 113.7(2) . . ?
C14 N2 C18 122.3(3) . . ?
C14 N2 Cu1 118.8(3) . . ?
C18 N2 Cu1 118.8(3) . . ?
C23 N3 C19 119.1(3) . . ?
C23 N3 Cu1 126.4(3) . . ?
C19 N3 Cu1 114.2(3) . . ?
C24 N4 C28 118.9(3) . . ?
C24 N4 Cu2 127.2(3) . . ?
C28 N4 Cu2 113.4(3) . . ?
C29 N5 C33 123.1(3) . . ?
C29 N5 Cu2 118.0(3) . . ?
C33 N5 Cu2 118.6(3) . . ?
C38 N6 C34 118.4(4) . . ?
C38 N6 Cu2 127.8(3) . . ?
C34 N6 Cu2 113.8(3) . . ?
C2 C1 C6 116.2(3) . . ?
C2 C1 C7 123.4(3) . . ?
C6 C1 C7 120.4(3) . . ?
F1 C2 C1 117.8(3) . . ?
F1 C2 C3 117.0(3) . . ?
C1 C2 C3 125.3(3) . . ?
C2 C3 C4 115.7(3) . . ?
C2 C3 C8 124.4(3) . . ?
C4 C3 C8 119.9(3) . . ?
F2 C4 C5 118.8(3) . . ?
F2 C4 C3 119.4(3) . . ?
C5 C4 C3 121.7(3) . . ?
F3 C5 C4 120.0(3) . . ?
F3 C5 C6 120.3(3) . . ?
C4 C5 C6 119.7(3) . . ?
F4 C6 C5 118.7(3) . . ?
F4 C6 C1 119.9(3) . . ?
C5 C6 C1 121.4(3) . . ?
O1 C7 O2 125.9(4) . . ?
O1 C7 C1 121.2(4) . . ?
O2 C7 C1 112.8(3) . . ?
O4 C8 O3 127.0(3) . . ?
O4 C8 C3 118.4(3) . . ?
O3 C8 C3 114.6(3) . . ?
N1 C9 C10 122.3(4) . . ?
C11 C10 C9 118.8(4) . . ?
C10 C11 C12 119.9(4) . . ?
C13 C12 C11 119.2(4) . . ?
N1 C13 C12 121.0(4) . . ?
N1 C13 C14 113.8(3) . . ?
C12 C13 C14 125.2(4) . . ?
N2 C14 C15 120.4(4) . . ?
N2 C14 C13 113.1(3) . . ?
C15 C14 C13 126.5(4) . . ?
C16 C15 C14 117.3(4) . . ?
C17 C16 C15 121.4(4) . . ?
C16 C17 C18 118.5(4) . . ?
N2 C18 C17 120.0(4) . . ?
N2 C18 C19 112.9(3) . . ?
C17 C18 C19 127.1(4) . . ?
N3 C19 C20 121.2(4) . . ?
N3 C19 C18 113.7(3) . . ?
C20 C19 C18 125.0(4) . . ?
C21 C20 C19 118.4(4) . . ?
C22 C21 C20 121.1(5) . . ?
C21 C22 C23 117.7(5) . . ?
N3 C23 C22 122.3(4) . . ?
N4 C24 C25 123.0(4) . . ?
C26 C25 C24 117.9(4) . . ?
C27 C26 C25 120.1(4) . . ?
C26 C27 C28 119.3(4) . . ?
N4 C28 C27 120.8(4) . . ?
N4 C28 C29 114.0(4) . . ?
C27 C28 C29 125.2(4) . . ?
N5 C29 C30 119.6(4) . . ?
N5 C29 C28 113.3(3) . . ?
C30 C29 C28 127.1(5) . . ?
C31 C30 C29 118.2(5) . . ?
C30 C31 C32 121.7(5) . . ?
C31 C32 C33 118.0(5) . . ?
N5 C33 C32 119.5(4) . . ?
N5 C33 C34 113.3(3) . . ?
C32 C33 C34 127.2(4) . . ?
N6 C34 C35 121.9(4) . . ?
N6 C34 C33 114.1(4) . . ?
C35 C34 C33 124.0(4) . . ?
C34 C35 C36 118.6(4) . . ?
C37 C36 C35 119.8(4) . . ?
C36 C37 C38 119.2(5) . . ?
N6 C38 C37 122.0(4) . . ?
O8 Cl1 O7 111.4(2) . . ?
O8 Cl1 O6 110.5(2) . . ?
O7 Cl1 O6 109.52(19) . . ?
O8 Cl1 O5 108.19(18) . . ?
O7 Cl1 O5 108.66(17) . . ?
O6 Cl1 O5 108.45(18) . . ?
Cl1 O5 Cu1 124.56(15) . . ?
O10A Cl2 O10 33.5(7) . . ?
O10A Cl2 O12 86.5(9) . . ?
O10 Cl2 O12 112.9(5) . . ?
O10A Cl2 O9A 117.0(9) . . ?
O10 Cl2 O9A 137.4(9) . . ?
O12 Cl2 O9A 82.9(7) . . ?
O10A Cl2 O11A 119.2(9) . . ?
O10 Cl2 O11A 86.1(7) . . ?
O12 Cl2 O11A 129.4(9) . . ?
O9A Cl2 O11A 115.0(11) . . ?
O10A Cl2 O9 95.0(8) . . ?
O10 Cl2 O9 102.2(4) . . ?
O12 Cl2 O9 112.6(4) . . ?
O9A Cl2 O9 37.7(7) . . ?
O11A Cl2 O9 107.9(10) . . ?
O10A Cl2 O11 141.6(8) . . ?
O10 Cl2 O11 109.9(3) . . ?
O12 Cl2 O11 110.7(4) . . ?
O9A Cl2 O11 99.5(7) . . ?
O11A Cl2 O11 24.8(8) . . ?
O9 Cl2 O11 108.3(4) . . ?
O10A Cl2 O12A 95.6(10) . . ?
O10 Cl2 O12A 108.6(9) . . ?
O12 Cl2 O12A 28.9(7) . . ?
O9A Cl2 O12A 103.0(9) . . ?
O11A Cl2 O12A 101.5(10) . . ?
O9 Cl2 O12A 138.5(8) . . ?
O11 Cl2 O12A 86.9(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 887475'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H22 Cu2 F8 N6 O8, 6(H2 O)'
_chemical_formula_sum            'C46 H34 Cu2 F8 N6 O14'
_chemical_formula_weight         1173.87

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'
F F 0.0171 0.0103 '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                   9.6850(10)
_cell_length_b                   10.5570(10)
_cell_length_c                   12.3960(10)
_cell_angle_alpha                107.106(2)
_cell_angle_beta                 100.958(2)
_cell_angle_gamma                96.022(2)
_cell_volume                     1171.67(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6095
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.32

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    1.015
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_T_max  0.8677
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            13175
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4281
_reflns_number_gt                3355
_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4281
_refine_ls_number_parameters     371
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.953
_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
Cu1 Cu 0.16818(3) -0.03740(3) 0.77400(3) 0.04241(13) Uani 1 1 d . . . . .
F1 F 0.23931(17) 0.12249(16) 0.52502(13) 0.0558(4) Uani 1 1 d . . . . .
F2 F -0.0808(2) 0.42493(19) 0.57023(16) 0.0722(5) Uani 1 1 d . . . . .
F3 F 0.0443(3) 0.53018(19) 0.79891(17) 0.0905(7) Uani 1 1 d . . . . .
F4 F 0.2623(2) 0.42644(18) 0.89240(14) 0.0773(6) Uani 1 1 d . . . . .
O1 O 0.3541(2) 0.1011(2) 0.77215(18) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.5015(2) 0.2817(3) 0.7849(2) 0.0921(9) Uani 1 1 d . . . . .
O3 O 0.0974(2) -0.11485(19) 0.60816(15) 0.0483(5) Uani 1 1 d . . . . .
O4 O -0.0549(2) -0.2492(2) 0.65515(16) 0.0632(6) Uani 1 1 d . . . . .
N1 N 0.0288(2) 0.0928(2) 0.8064(2) 0.0471(6) Uani 1 1 d . . . . .
C2 C 0.0447(3) 0.1590(3) 0.9207(3) 0.0541(8) Uani 1 1 d . . . . .
C3 C -0.0387(4) 0.2566(3) 0.9561(3) 0.0730(10) Uani 1 1 d . . . . .
H3 H -0.0256 0.3040 1.0345 0.088 Uiso 1 1 calc R U . . .
C4 C -0.1389(4) 0.2825(4) 0.8763(4) 0.0833(12) Uani 1 1 d . . . . .
H4 H -0.1950 0.3471 0.8998 0.100 Uiso 1 1 calc R U . . .
C5 C -0.1565(4) 0.2130(3) 0.7616(4) 0.0704(9) Uani 1 1 d . . . . .
H5 H -0.2255 0.2285 0.7058 0.084 Uiso 1 1 calc R U . . .
C6 C -0.0704(3) 0.1197(3) 0.7298(3) 0.0549(8) Uani 1 1 d . . . . .
H6 H -0.0819 0.0732 0.6514 0.066 Uiso 1 1 calc R U . . .
N7 N 0.2101(2) 0.0152(2) 0.94157(19) 0.0468(6) Uani 1 1 d . . . . .
C8 C 0.1491(3) 0.1155(3) 0.9983(2) 0.0531(8) Uani 1 1 d . . . . .
C9 C 0.1855(4) 0.1609(4) 1.1194(3) 0.0664(9) Uani 1 1 d . . . . .
H9 H 0.1455 0.2301 1.1611 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2816(4) 0.1010(4) 1.1756(3) 0.0741(11) Uani 1 1 d . . . . .
H10 H 0.3073 0.1313 1.2562 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3409(4) -0.0029(4) 1.1155(3) 0.0645(9) Uani 1 1 d . . . . .
H11 H 0.4056 -0.0431 1.1543 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3006(3) -0.0456(3) 0.9951(2) 0.0486(7) Uani 1 1 d . . . . .
N13 N 0.2941(2) -0.1729(2) 0.80065(19) 0.0446(6) Uani 1 1 d . . . . .
C14 C 0.3461(3) -0.1567(3) 0.9141(3) 0.0486(7) Uani 1 1 d . . . . .
C15 C 0.4320(3) -0.2421(3) 0.9481(3) 0.0622(9) Uani 1 1 d . . . . .
H15 H 0.4664 -0.2304 1.0263 0.075 Uiso 1 1 calc R U . . .
C16 C 0.4653(3) -0.3435(4) 0.8645(3) 0.0680(9) Uani 1 1 d . . . . .
H16 H 0.5228 -0.4016 0.8855 0.082 Uiso 1 1 calc R U . . .
C17 C 0.4134(3) -0.3593(3) 0.7496(3) 0.0626(8) Uani 1 1 d . . . . .
H17 H 0.4358 -0.4276 0.6919 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3276(3) -0.2722(3) 0.7210(3) 0.0531(7) Uani 1 1 d . . . . .
H18 H 0.2919 -0.2835 0.6431 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2583(3) 0.2717(3) 0.7103(2) 0.0441(7) Uani 1 1 d . . . . .
C20 C 0.1907(3) 0.2238(3) 0.5939(2) 0.0405(6) Uani 1 1 d . . . . .
C21 C 0.0772(3) 0.2710(3) 0.5432(2) 0.0389(6) Uani 1 1 d . . . . .
C22 C 0.0306(3) 0.3754(3) 0.6142(2) 0.0492(7) Uani 1 1 d . . . . .
C23 C 0.0931(4) 0.4283(3) 0.7304(3) 0.0567(8) Uani 1 1 d . . . . .
C24 C 0.2044(3) 0.3758(3) 0.7765(2) 0.0527(8) Uani 1 1 d . . . . .
C25 C 0.3822(3) 0.2140(3) 0.7608(2) 0.0516(7) Uani 1 1 d . . . . .
C26 C -0.0077(3) -0.2093(3) 0.5843(2) 0.0415(6) Uani 1 1 d . . . . .
O5 O 0.6676(6) 0.5907(7) 0.5726(5) 0.118(2) Uani 0.810(4) 1 d . U P A 1
H5A H 0.7563 0.6046 0.5748 0.177 Uiso 0.810(4) 1 d R U P A 1
H5B H 0.6005 0.6140 0.5316 0.177 Uiso 0.810(4) 1 d R U P A 1
O6 O 0.5501(4) 0.3318(3) 0.5623(3) 0.1113(15) Uani 0.810(4) 1 d . . P A 1
H6A H 0.5307 0.3185 0.6225 0.167 Uiso 0.810(4) 1 d R U P A 1
H6B H 0.5865 0.4099 0.5650 0.167 Uiso 0.810(4) 1 d R U P A 1
O7 O 0.4891(6) 0.9354(5) 0.5827(4) 0.1349(19) Uani 0.810(4) 1 d . U P A 1
H7A H 0.4482 0.9778 0.6337 0.202 Uiso 0.810(4) 1 d R U P A 1
H7B H 0.4790 0.8542 0.5396 0.202 Uiso 0.810(4) 1 d R U P A 1
O5B O 0.699(3) 0.584(3) 0.628(3) 0.112(6) Uani 0.190(4) 1 d . U P A 2
H5C H 0.7854 0.5761 0.6501 0.168 Uiso 0.190(4) 1 d R U P A 2
H5D H 0.6793 0.5638 0.5550 0.168 Uiso 0.190(4) 1 d R U P A 2
O6B O 0.7009(12) 0.4911(12) 0.7971(12) 0.082(5) Uani 0.190(4) 1 d . . P A 2
H6C H 0.6323 0.4277 0.7852 0.123 Uiso 0.190(4) 1 d R U P A 2
H6D H 0.6976 0.5214 0.7405 0.123 Uiso 0.190(4) 1 d R U P A 2
O7B O 0.364(2) 0.8784(16) 0.4986(15) 0.106(4) Uani 0.190(4) 1 d . U P A 2
H7C H 0.2919 0.8862 0.5287 0.159 Uiso 0.190(4) 1 d R U P A 2
H7D H 0.4291 0.9385 0.4981 0.159 Uiso 0.190(4) 1 d R U P A 2


_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 O3 1.9293(18) . ?
Cu1 N7 1.934(2) . ?
Cu1 N13 2.034(2) . ?
Cu1 N1 2.036(2) . ?
Cu1 O1 2.206(2) . ?
Cu1 O4 2.771(2) . ?
F1 C20 1.348(3) . ?
F2 C22 1.340(3) . ?
F3 C23 1.350(3) . ?
F4 C24 1.358(3) . ?
O1 C25 1.249(3) . ?
O2 C25 1.227(3) . ?
O3 C26 1.272(3) . ?
O4 C26 1.219(3) . ?
N1 C6 1.331(4) . ?
N1 C2 1.353(4) . ?
C2 C3 1.397(4) . ?
C2 C8 1.465(4) . ?
C3 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N7 C12 1.329(4) . ?
N7 C8 1.348(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.471(4) . ?
N13 C18 1.328(4) . ?
N13 C14 1.353(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.380(4) . ?
C19 C20 1.381(4) . ?
C19 C25 1.515(4) . ?
C20 C21 1.374(4) . ?
C21 C22 1.371(4) . ?
C21 C26 1.507(4) 2_556 ?
C22 C23 1.370(4) . ?
C23 C24 1.370(4) . ?
C26 C21 1.507(4) 2_556 ?
O5 H5A 0.8500 . ?
O5 H5B 0.8502 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8502 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8501 . ?
O5B H5C 0.8500 . ?
O5B H5D 0.8500 . ?
O6B H6C 0.8500 . ?
O6B H6D 0.8496 . ?
O7B H7C 0.8500 . ?
O7B H7D 0.8502 . ?

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
O3 Cu1 N7 168.98(8) . . ?
O3 Cu1 N13 98.94(9) . . ?
N7 Cu1 N13 79.89(10) . . ?
O3 Cu1 N1 98.62(9) . . ?
N7 Cu1 N1 80.27(10) . . ?
N13 Cu1 N1 157.79(9) . . ?
O3 Cu1 O1 97.34(8) . . ?
N7 Cu1 O1 93.64(8) . . ?
N13 Cu1 O1 91.02(8) . . ?
N1 Cu1 O1 100.12(8) . . ?
O3 Cu1 O4 52.57(7) . . ?
N7 Cu1 O4 116.41(8) . . ?
N13 Cu1 O4 88.84(8) . . ?
N1 Cu1 O4 91.09(8) . . ?
O1 Cu1 O4 149.39(7) . . ?
C25 O1 Cu1 139.3(2) . . ?
C26 O3 Cu1 110.31(16) . . ?
C26 O4 Cu1 71.73(16) . . ?
C6 N1 C2 118.7(3) . . ?
C6 N1 Cu1 127.9(2) . . ?
C2 N1 Cu1 113.4(2) . . ?
N1 C2 C3 120.0(3) . . ?
N1 C2 C8 114.6(3) . . ?
C3 C2 C8 125.4(3) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 122.9(3) . . ?
N1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C12 N7 C8 123.3(3) . . ?
C12 N7 Cu1 118.8(2) . . ?
C8 N7 Cu1 117.8(2) . . ?
N7 C8 C9 118.6(3) . . ?
N7 C8 C2 113.2(3) . . ?
C9 C8 C2 128.1(3) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N7 C12 C11 120.0(3) . . ?
N7 C12 C14 112.9(2) . . ?
C11 C12 C14 127.0(3) . . ?
C18 N13 C14 118.7(3) . . ?
C18 N13 Cu1 127.60(19) . . ?
C14 N13 Cu1 113.7(2) . . ?
N13 C14 C15 121.4(3) . . ?
N13 C14 C12 114.4(3) . . ?
C15 C14 C12 124.2(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N13 C18 C17 122.5(3) . . ?
N13 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C24 C19 C20 114.9(3) . . ?
C24 C19 C25 122.8(3) . . ?
C20 C19 C25 122.3(3) . . ?
F1 C20 C21 117.5(2) . . ?
F1 C20 C19 117.4(2) . . ?
C21 C20 C19 125.0(3) . . ?
C22 C21 C20 116.7(2) . . ?
C22 C21 C26 122.2(2) . 2_556 ?
C20 C21 C26 121.1(2) . 2_556 ?
F2 C22 C23 119.0(3) . . ?
F2 C22 C21 119.6(3) . . ?
C23 C22 C21 121.4(3) . . ?
F3 C23 C22 120.3(3) . . ?
F3 C23 C24 120.4(3) . . ?
C22 C23 C24 119.3(3) . . ?
F4 C24 C23 118.6(3) . . ?
F4 C24 C19 118.7(3) . . ?
C23 C24 C19 122.7(3) . . ?
O2 C25 O1 126.0(3) . . ?
O2 C25 C19 116.8(3) . . ?
O1 C25 C19 117.2(2) . . ?
O4 C26 O3 125.4(2) . . ?
O4 C26 C21 120.0(2) . 2_556 ?
O3 C26 C21 114.6(2) . 2_556 ?
H5A O5 H5B 127.7 . . ?
H6A O6 H6B 120.3 . . ?
H7A O7 H7B 135.1 . . ?
H5C O5B H5D 107.7 . . ?
H6C O6B H6D 113.1 . . ?
H7C O7B H7D 130.1 . . ?

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
O5 H5A O4 0.85 2.13 2.848(6) 142.2 1_665
O5 H5A F2 0.85 2.59 3.145(7) 124.4 1_655
O5 H5B O6 0.85 1.93 2.782(7) 179.2 2_666
O6 H6A O2 0.85 2.22 3.068(5) 174.6 .
O6 H6B O5 0.85 1.95 2.805(7) 178.9 .
O7 H7A O1 0.85 2.24 3.085(4) 175.9 1_565
O7 H7B O6 0.85 1.95 2.805(6) 178.2 2_666
O5B H5C O4 0.85 2.26 2.72(3) 114.1 1_665
O5B H5C F2 0.85 2.28 2.92(3) 131.9 1_655
O6B H6C O2 0.85 1.89 2.726(12) 168.7 .
O6B H6D O5B 0.85 1.71 2.55(3) 177.5 .
O7B H7C O3 0.85 2.29 3.133(17) 174.3 1_565
O7B H7D O7B 0.85 2.62 3.47(4) 178.3 2_676

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.063

