# 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 2020

####################################################################### 
# 
# 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_r
_database_code_depnum_ccdc_archive 'CCDC 1956605'
loop_
_audit_author_name
_audit_author_address
'Lars Eriksson'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-09-29 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Br2 Cu N2 O4, N O3'
_chemical_formula_sum            'C16 H13 Br2 Cu N3 O7'
_chemical_formula_weight         582.65

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'
Br Br -0.2901 2.4595 '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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1803(2)
_cell_length_b                   11.3573(2)
_cell_length_c                   15.1698(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.906(2)
_cell_angle_gamma                90
_cell_volume                     1919.17(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12196
_cell_measurement_theta_min      3.3140
_cell_measurement_theta_max      30.5920

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    5.348
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 16.5467
_diffrn_reflns_number            43533
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.238
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3918
_reflns_number_gt                3553
_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.
;

_computing_data_collection       'CrysAlisPro, (Rigaku, 2017)'
_computing_cell_refinement       'CrysAlisPro, (Rigaku, 2017)'
_computing_data_reduction        'CrysAlisPro, (Rigaku, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0558P)²+6.4601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3918
_refine_ls_number_parameters     271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.103
_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
Cu1 Cu 0.59775(5) 0.48208(5) 0.22509(4) 0.03570(18) Uani 1 1 d . . . . .
C2 C 0.3965(6) 0.7460(6) 0.0147(4) 0.0622(17) Uani 1 1 d . . . . .
H2A H 0.418165 0.757416 -0.044564 0.093 Uiso 1 1 calc R U . . .
H2B H 0.458828 0.776480 0.055898 0.093 Uiso 1 1 calc R U . . .
H2C H 0.322741 0.786755 0.022134 0.093 Uiso 1 1 calc R U . . .
C3 C 0.3809(5) 0.6220(6) 0.0308(4) 0.0481(13) Uani 1 1 d . . . . .
C4 C 0.4406(4) 0.5560(6) 0.0966(3) 0.0426(12) Uani 1 1 d . . . . .
C5 C 0.4145(4) 0.4366(6) 0.1057(3) 0.0462(13) Uani 1 1 d . . . . .
C6 C 0.3257(5) 0.3853(6) 0.0422(4) 0.0520(14) Uani 1 1 d . . . . .
H6 H 0.305904 0.305956 0.044786 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2744(5) 0.4531(8) -0.0185(4) 0.0649(19) Uani 1 1 d . . . . .
H7 H 0.217092 0.419372 -0.058839 0.078 Uiso 1 1 calc R U . . .
O8 O 0.2976(3) 0.5686(4) -0.0278(2) 0.0540(10) Uani 1 1 d . . . . .
O9 O 0.5248(3) 0.6054(4) 0.1542(2) 0.0467(9) Uani 1 1 d . . . . .
O10 O 0.4721(3) 0.3810(4) 0.1671(3) 0.0514(10) Uani 1 1 d . . . . .
O11 O 0.5142(4) 0.5208(5) 0.3548(3) 0.0565(11) Uani 1 1 d D . . . .
H11A H 0.551(6) 0.525(7) 0.400(4) 0.085 Uiso 1 1 d D U . . .
H11B H 0.457(5) 0.487(7) 0.365(4) 0.085 Uiso 1 1 d D U . . .
N12 N 0.7515(4) 0.5886(5) 0.5645(3) 0.0519(12) Uani 1 1 d . . . . .
O13 O 0.8458(5) 0.6348(7) 0.5514(5) 0.111(2) Uani 1 1 d . . . . .
O14 O 0.7291(8) 0.5674(7) 0.6386(4) 0.124(3) Uani 1 1 d . . . . .
O15 O 0.6785(7) 0.5705(8) 0.5048(6) 0.143(3) Uani 1 1 d . . . . .
N16 N 0.7024(3) 0.3481(4) 0.2655(2) 0.0326(8) Uani 1 1 d . . . . .
C17 C 0.6765(4) 0.2342(4) 0.2518(3) 0.0374(10) Uani 1 1 d . . . . .
H17 H 0.603275 0.214046 0.221856 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7547(4) 0.1457(4) 0.2808(3) 0.0375(10) Uani 1 1 d . . . . .
H18 H 0.736631 0.066970 0.269139 0.045 Uiso 1 1 calc R U . . .
C19 C 0.8604(4) 0.1782(4) 0.3274(3) 0.0338(10) Uani 1 1 d . . . . .
C20 C 0.8896(4) 0.2951(4) 0.3416(3) 0.0325(9) Uani 1 1 d . . . . .
H20 H 0.961539 0.316862 0.372686 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8080(4) 0.3787(4) 0.3080(3) 0.0297(9) Uani 1 1 d . . . . .
C22 C 0.8304(4) 0.5065(4) 0.3131(3) 0.0302(9) Uani 1 1 d . . . . .
C23 C 0.9320(4) 0.5580(4) 0.3555(3) 0.0337(10) Uani 1 1 d . . . . .
H23 H 0.991471 0.513054 0.385947 0.040 Uiso 1 1 calc R U . . .
C24 C 0.9411(4) 0.6795(4) 0.3504(3) 0.0371(10) Uani 1 1 d . . . . .
C25 C 0.8543(5) 0.7457(4) 0.3035(4) 0.0435(12) Uani 1 1 d . . . . .
H25 H 0.862446 0.826857 0.298133 0.052 Uiso 1 1 calc R U . . .
C26 C 0.7556(5) 0.6882(5) 0.2649(4) 0.0441(12) Uani 1 1 d . . . . .
H26 H 0.695253 0.732126 0.234441 0.053 Uiso 1 1 calc R U . . .
N27 N 0.7427(3) 0.5722(3) 0.2693(3) 0.0338(8) Uani 1 1 d . . . . .
Br1 Br 0.96541(5) 0.05877(5) 0.37247(4) 0.05055(19) Uani 1 1 d . . . . .
Br2 Br 1.07666(5) 0.75376(5) 0.40813(4) 0.0529(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
Cu1 O9 1.906(4) . ?
Cu1 O10 1.962(4) . ?
Cu1 N16 1.985(4) . ?
Cu1 N27 1.985(4) . ?
Cu1 O11 2.291(4) . ?
C2 C3 1.442(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O8 1.372(7) . ?
C3 C4 1.376(7) . ?
C4 O9 1.349(6) . ?
C4 C5 1.396(9) . ?
C5 O10 1.257(7) . ?
C5 C6 1.446(7) . ?
C6 C7 1.295(9) . ?
C6 H6 0.9300 . ?
C7 O8 1.347(9) . ?
C7 H7 0.9300 . ?
O11 H11A 0.77(5) . ?
O11 H11B 0.77(5) . ?
N12 O15 1.184(7) . ?
N12 O14 1.197(7) . ?
N12 O13 1.210(7) . ?
N16 C17 1.338(6) . ?
N16 C21 1.342(6) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(7) . ?
C19 Br1 1.883(5) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.473(6) . ?
C22 N27 1.359(6) . ?
C22 C23 1.386(6) . ?
C23 C24 1.386(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(7) . ?
C24 Br2 1.883(5) . ?
C25 C26 1.370(7) . ?
C25 H25 0.9300 . ?
C26 N27 1.328(7) . ?
C26 H26 0.9300 . ?

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
O9 Cu1 O10 85.49(17) . . ?
O9 Cu1 N16 161.86(16) . . ?
O10 Cu1 N16 94.03(16) . . ?
O9 Cu1 N27 96.31(16) . . ?
O10 Cu1 N27 170.24(17) . . ?
N16 Cu1 N27 81.26(15) . . ?
O9 Cu1 O11 99.05(17) . . ?
O10 Cu1 O11 99.68(17) . . ?
N16 Cu1 O11 98.91(17) . . ?
N27 Cu1 O11 89.53(17) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O8 C3 C4 119.3(6) . . ?
O8 C3 C2 114.0(5) . . ?
C4 C3 C2 126.6(6) . . ?
O9 C4 C3 120.8(6) . . ?
O9 C4 C5 118.7(5) . . ?
C3 C4 C5 120.5(5) . . ?
O10 C5 C4 117.5(5) . . ?
O10 C5 C6 124.8(6) . . ?
C4 C5 C6 117.6(5) . . ?
C7 C6 C5 118.1(6) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 O8 125.2(6) . . ?
C6 C7 H7 117.4 . . ?
O8 C7 H7 117.4 . . ?
C7 O8 C3 119.3(5) . . ?
C4 O9 Cu1 107.5(3) . . ?
C5 O10 Cu1 109.9(4) . . ?
Cu1 O11 H11A 123(6) . . ?
Cu1 O11 H11B 118(6) . . ?
H11A O11 H11B 104.3(19) . . ?
O15 N12 O14 119.9(8) . . ?
O15 N12 O13 120.2(7) . . ?
O14 N12 O13 119.8(7) . . ?
C17 N16 C21 119.7(4) . . ?
C17 N16 Cu1 125.4(3) . . ?
C21 N16 Cu1 114.9(3) . . ?
N16 C17 C18 122.1(4) . . ?
N16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 117.5(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 Br1 118.4(4) . . ?
C20 C19 Br1 120.3(4) . . ?
C19 C20 C21 117.6(4) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
N16 C21 C20 121.6(4) . . ?
N16 C21 C22 114.8(4) . . ?
C20 C21 C22 123.6(4) . . ?
N27 C22 C23 121.5(4) . . ?
N27 C22 C21 113.7(4) . . ?
C23 C22 C21 124.7(4) . . ?
C22 C23 C24 117.2(4) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C25 C24 C23 121.3(4) . . ?
C25 C24 Br2 120.0(4) . . ?
C23 C24 Br2 118.7(4) . . ?
C26 C25 C24 117.8(5) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
N27 C26 C25 122.6(5) . . ?
N27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 N27 C22 119.5(4) . . ?
C26 N27 Cu1 125.7(3) . . ?
C22 N27 Cu1 114.6(3) . . ?

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
O8 C3 C4 O9 178.7(4) . . . . ?
C2 C3 C4 O9 -0.8(8) . . . . ?
O8 C3 C4 C5 -2.0(8) . . . . ?
C2 C3 C4 C5 178.5(6) . . . . ?
O9 C4 C5 O10 -0.6(7) . . . . ?
C3 C4 C5 O10 180.0(5) . . . . ?
O9 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C5 C6 1.8(7) . . . . ?
O10 C5 C6 C7 -179.0(6) . . . . ?
C4 C5 C6 C7 -1.0(8) . . . . ?
C5 C6 C7 O8 0.4(10) . . . . ?
C6 C7 O8 C3 -0.6(9) . . . . ?
C4 C3 O8 C7 1.3(8) . . . . ?
C2 C3 O8 C7 -179.1(5) . . . . ?
C3 C4 O9 Cu1 -173.5(4) . . . . ?
C5 C4 O9 Cu1 7.1(5) . . . . ?
C4 C5 O10 Cu1 -6.1(6) . . . . ?
C6 C5 O10 Cu1 172.0(4) . . . . ?
C21 N16 C17 C18 0.6(7) . . . . ?
Cu1 N16 C17 C18 179.0(4) . . . . ?
N16 C17 C18 C19 2.1(7) . . . . ?
C17 C18 C19 C20 -2.7(7) . . . . ?
C17 C18 C19 Br1 177.1(4) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
Br1 C19 C20 C21 -179.1(3) . . . . ?
C17 N16 C21 C20 -2.8(7) . . . . ?
Cu1 N16 C21 C20 178.7(3) . . . . ?
C17 N16 C21 C22 175.6(4) . . . . ?
Cu1 N16 C21 C22 -3.0(5) . . . . ?
C19 C20 C21 N16 2.1(7) . . . . ?
C19 C20 C21 C22 -176.0(4) . . . . ?
N16 C21 C22 N27 -3.6(6) . . . . ?
C20 C21 C22 N27 174.7(4) . . . . ?
N16 C21 C22 C23 178.5(4) . . . . ?
C20 C21 C22 C23 -3.2(7) . . . . ?
N27 C22 C23 C24 -0.7(7) . . . . ?
C21 C22 C23 C24 177.0(4) . . . . ?
C22 C23 C24 C25 -1.6(7) . . . . ?
C22 C23 C24 Br2 179.2(3) . . . . ?
C23 C24 C25 C26 2.8(8) . . . . ?
Br2 C24 C25 C26 -178.0(4) . . . . ?
C24 C25 C26 N27 -1.8(9) . . . . ?
C25 C26 N27 C22 -0.4(8) . . . . ?
C25 C26 N27 Cu1 174.3(4) . . . . ?
C23 C22 N27 C26 1.7(7) . . . . ?
C21 C22 N27 C26 -176.3(4) . . . . ?
C23 C22 N27 Cu1 -173.6(3) . . . . ?
C21 C22 N27 Cu1 8.4(5) . . . . ?

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
C7 H7 Br1 0.93 2.93 3.703(6) 141.9 4_465
O11 H11A O15 0.77(5) 2.11(5) 2.856(7) 164(7) .
O11 H11B O14 0.77(5) 2.17(5) 2.909(10) 161(8) 3_666
C17 H17 O10 0.93 2.50 3.025(6) 116.3 .
C18 H18 O14 0.93 2.50 3.237(8) 136.9 4_565
C20 H20 O13 0.93 2.42 3.346(7) 176.7 3_766
C23 H23 O13 0.93 2.60 3.516(8) 170.7 3_766
C25 H25 Br1 0.93 3.05 3.880(5) 149.2 1_565
C26 H26 O9 0.93 2.61 3.103(6) 114.0 .

_refine_diff_density_max         1.085
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_r_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1956606'
loop_
_audit_author_name
_audit_author_address
'Lars Eriksson'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-09-29 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cu N2 O3, F6 P'
_chemical_formula_sum            'C16 H13 Cu F6 N2 O3 P'
_chemical_formula_weight         489.79

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'
Cu Cu 0.3201 1.2651 '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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0772(2)
_cell_length_b                   14.8170(3)
_cell_length_c                   15.2106(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.928(2)
_cell_angle_gamma                90
_cell_volume                     1781.10(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10743
_cell_measurement_theta_min      3.5040
_cell_measurement_theta_max      30.4010

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.399
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86983
_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 16.5467
_diffrn_reflns_number            27438
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.350
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3637
_reflns_number_gt                3272
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0750P)²+3.0841P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3637
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Cu Cu 0.85787(5) 0.44154(3) 0.52880(3) 0.03439(17) Uani 1 1 d . . . . .
C1 C 1.0715(4) 0.6181(2) 0.7170(2) 0.0386(7) Uani 1 1 d . . . . .
C2 C 1.0257(4) 0.5480(2) 0.6594(2) 0.0335(7) Uani 1 1 d . . . . .
C3 C 1.0631(4) 0.4575(2) 0.6903(2) 0.0362(7) Uani 1 1 d . . . . .
C4 C 1.1619(5) 0.4467(3) 0.7781(3) 0.0514(10) Uani 1 1 d . . . . .
H4 H 1.193876 0.389377 0.800283 0.062 Uiso 1 1 calc R U . . .
C5 C 1.2086(6) 0.5196(3) 0.8286(3) 0.0560(10) Uani 1 1 d . . . . .
H5 H 1.275294 0.511667 0.885702 0.067 Uiso 1 1 calc R U . . .
O6 O 1.1641(4) 0.60329(19) 0.80110(17) 0.0499(6) Uani 1 1 d . . . . .
C7 C 1.0265(6) 0.7144(3) 0.6993(3) 0.0505(9) Uani 1 1 d . . . . .
H7A H 0.961371 0.735096 0.741464 0.076 Uiso 1 1 calc R U . . .
H7B H 0.961085 0.720778 0.639316 0.076 Uiso 1 1 calc R U . . .
H7C H 1.128018 0.749668 0.705678 0.076 Uiso 1 1 calc R U . . .
O8 O 0.9427(3) 0.55758(15) 0.57455(16) 0.0370(5) Uani 1 1 d . . . . .
O9 O 1.0043(3) 0.39267(16) 0.63748(17) 0.0417(6) Uani 1 1 d . . . . .
N10 N 0.6655(3) 0.49212(19) 0.43980(18) 0.0351(6) Uani 1 1 d . . . . .
C11 C 0.6291(5) 0.5799(2) 0.4266(2) 0.0406(8) Uani 1 1 d . . . . .
H11 H 0.700156 0.622640 0.459839 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4888(5) 0.6085(3) 0.3649(3) 0.0480(9) Uani 1 1 d . . . . .
H12 H 0.465658 0.669753 0.356117 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3836(5) 0.5447(3) 0.3166(3) 0.0504(9) Uani 1 1 d . . . . .
H13 H 0.288403 0.562575 0.274730 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4198(5) 0.4544(3) 0.3306(3) 0.0463(9) Uani 1 1 d . . . . .
H14 H 0.348838 0.410811 0.298849 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5636(4) 0.4295(2) 0.3925(2) 0.0363(7) Uani 1 1 d . . . . .
C16 C 0.6187(4) 0.3355(2) 0.4127(2) 0.0365(7) Uani 1 1 d . . . . .
C17 C 0.5418(5) 0.2606(3) 0.3672(3) 0.0479(9) Uani 1 1 d . . . . .
H17 H 0.448223 0.267162 0.320376 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6064(6) 0.1758(3) 0.3925(3) 0.0526(10) Uani 1 1 d . . . . .
H18 H 0.555171 0.124681 0.363444 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7467(6) 0.1675(3) 0.4608(3) 0.0504(9) Uani 1 1 d . . . . .
H19 H 0.792410 0.110970 0.477815 0.060 Uiso 1 1 calc R U . . .
C20 C 0.8183(5) 0.2443(3) 0.5035(3) 0.0443(8) Uani 1 1 d . . . . .
H20 H 0.912472 0.238940 0.550109 0.053 Uiso 1 1 calc R U . . .
N21 N 0.7561(4) 0.32639(19) 0.47982(19) 0.0367(6) Uani 1 1 d . . . . .
P P 0.29230(14) 0.37068(7) 0.07565(7) 0.0495(3) Uani 1 1 d . . . . .
F1 F 0.3050(10) 0.4600(3) 0.1292(3) 0.175(3) Uani 1 1 d . . . . .
F2 F 0.3836(6) 0.4223(3) 0.0092(3) 0.1337(18) Uani 1 1 d . . . . .
F3 F 0.1230(5) 0.4030(4) 0.0144(4) 0.149(2) Uani 1 1 d . . . . .
F4 F 0.2759(10) 0.2840(3) 0.0200(3) 0.178(3) Uani 1 1 d . . . . .
F5 F 0.2058(7) 0.3210(4) 0.1421(3) 0.164(2) Uani 1 1 d . . . . .
F6 F 0.4587(5) 0.3422(4) 0.1373(4) 0.157(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
Cu O8 1.927(2) . ?
Cu O9 1.962(2) . ?
Cu N21 1.972(3) . ?
Cu N10 1.985(3) . ?
C1 O6 1.359(4) . ?
C1 C2 1.361(5) . ?
C1 C7 1.484(5) . ?
C2 O8 1.333(4) . ?
C2 C3 1.432(5) . ?
C3 O9 1.279(4) . ?
C3 C4 1.416(5) . ?
C4 C5 1.334(6) . ?
C4 H4 0.9300 . ?
C5 O6 1.335(5) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N10 C11 1.340(5) . ?
N10 C15 1.346(4) . ?
C11 C12 1.381(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.475(5) . ?
C16 N21 1.350(4) . ?
C16 C17 1.386(5) . ?
C17 C18 1.384(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 N21 1.336(5) . ?
C20 H20 0.9300 . ?
P F4 1.528(4) . ?
P F6 1.530(4) . ?
P F5 1.531(4) . ?
P F1 1.546(4) . ?
P F3 1.562(4) . ?
P F2 1.568(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
O8 Cu O9 85.28(10) . . ?
O8 Cu N21 176.22(11) . . ?
O9 Cu N21 97.51(11) . . ?
O8 Cu N10 94.55(11) . . ?
O9 Cu N10 164.78(11) . . ?
N21 Cu N10 82.10(12) . . ?
O6 C1 C2 120.4(3) . . ?
O6 C1 C7 113.1(3) . . ?
C2 C1 C7 126.4(3) . . ?
O8 C2 C1 123.9(3) . . ?
O8 C2 C3 116.6(3) . . ?
C1 C2 C3 119.5(3) . . ?
O9 C3 C4 124.9(3) . . ?
O9 C3 C2 118.1(3) . . ?
C4 C3 C2 117.1(3) . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 O6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
O6 C5 H5 118.4 . . ?
C5 O6 C1 120.3(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 O8 Cu 108.9(2) . . ?
C3 O9 Cu 109.5(2) . . ?
C11 N10 C15 119.9(3) . . ?
C11 N10 Cu 125.8(2) . . ?
C15 N10 Cu 114.2(2) . . ?
N10 C11 C12 121.6(4) . . ?
N10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.0(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N10 C15 C14 120.9(3) . . ?
N10 C15 C16 114.5(3) . . ?
C14 C15 C16 124.6(3) . . ?
N21 C16 C17 120.8(3) . . ?
N21 C16 C15 114.7(3) . . ?
C17 C16 C15 124.6(3) . . ?
C18 C17 C16 118.9(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 118.8(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N21 C20 C19 121.8(4) . . ?
N21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 N21 C16 119.9(3) . . ?
C20 N21 Cu 125.5(2) . . ?
C16 N21 Cu 114.4(2) . . ?
F4 P F6 94.1(4) . . ?
F4 P F5 87.8(3) . . ?
F6 P F5 85.7(3) . . ?
F4 P F1 178.0(3) . . ?
F6 P F1 87.7(4) . . ?
F5 P F1 93.0(4) . . ?
F4 P F3 87.8(4) . . ?
F6 P F3 178.0(4) . . ?
F5 P F3 94.5(3) . . ?
F1 P F3 90.4(3) . . ?
F4 P F2 92.9(3) . . ?
F6 P F2 93.4(3) . . ?
F5 P F2 178.9(3) . . ?
F1 P F2 86.2(3) . . ?
F3 P F2 86.3(3) . . ?

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 O8 -176.4(3) . . . . ?
C7 C1 C2 O8 5.4(6) . . . . ?
O6 C1 C2 C3 5.3(5) . . . . ?
C7 C1 C2 C3 -172.9(3) . . . . ?
O8 C2 C3 O9 -5.1(5) . . . . ?
C1 C2 C3 O9 173.3(3) . . . . ?
O8 C2 C3 C4 175.5(3) . . . . ?
C1 C2 C3 C4 -6.1(5) . . . . ?
O9 C3 C4 C5 -176.5(4) . . . . ?
C2 C3 C4 C5 2.9(6) . . . . ?
C3 C4 C5 O6 1.2(7) . . . . ?
C4 C5 O6 C1 -2.2(6) . . . . ?
C2 C1 O6 C5 -1.2(5) . . . . ?
C7 C1 O6 C5 177.2(4) . . . . ?
C1 C2 O8 Cu -166.1(3) . . . . ?
C3 C2 O8 Cu 12.2(4) . . . . ?
C4 C3 O9 Cu 174.4(3) . . . . ?
C2 C3 O9 Cu -4.9(4) . . . . ?
C15 N10 C11 C12 -0.3(5) . . . . ?
Cu N10 C11 C12 -177.8(3) . . . . ?
N10 C11 C12 C13 0.6(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C11 N10 C15 C14 -0.5(5) . . . . ?
Cu N10 C15 C14 177.2(3) . . . . ?
C11 N10 C15 C16 179.4(3) . . . . ?
Cu N10 C15 C16 -2.8(4) . . . . ?
C13 C14 C15 N10 1.1(6) . . . . ?
C13 C14 C15 C16 -178.8(3) . . . . ?
N10 C15 C16 N21 4.4(4) . . . . ?
C14 C15 C16 N21 -175.7(3) . . . . ?
N10 C15 C16 C17 -174.4(3) . . . . ?
C14 C15 C16 C17 5.6(6) . . . . ?
N21 C16 C17 C18 1.0(6) . . . . ?
C15 C16 C17 C18 179.7(3) . . . . ?
C16 C17 C18 C19 -1.2(6) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C18 C19 C20 N21 -0.6(6) . . . . ?
C19 C20 N21 C16 0.5(5) . . . . ?
C19 C20 N21 Cu -174.7(3) . . . . ?
C17 C16 N21 C20 -0.7(5) . . . . ?
C15 C16 N21 C20 -179.5(3) . . . . ?
C17 C16 N21 Cu 175.0(3) . . . . ?
C15 C16 N21 Cu -3.8(4) . . . . ?

_refine_diff_density_max         0.894
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_r_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1956607'
loop_
_audit_author_name
_audit_author_address
'Lars Eriksson'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-09-29 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cu2 N4 O6, 2(F6 P)'
_chemical_formula_sum            'C36 H26 Cu2 F12 N4 O6 P2'
_chemical_formula_weight         1027.63

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'
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'
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'
P P 0.1023 0.0942 '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                   8.153(2)
_cell_length_b                   11.328(3)
_cell_length_c                   22.236(7)
_cell_angle_alpha                93.697(7)
_cell_angle_beta                 92.344(7)
_cell_angle_gamma                107.709(7)
_cell_volume                     1948.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.15

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.283
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incotec 1myS'
_diffrn_measurement_device_type  'Bruker D8 Advance'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            60653
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_av_R_equivalents  0.2219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7395
_reflns_number_gt                4673
_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       'Apex3 (Bruker, 2017)'
_computing_cell_refinement       'Apex3 (Bruker, 2017)'
_computing_data_reduction        'Apex3 (Bruker, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+24.8850P] 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         7395
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.1266
_refine_ls_wR_factor_ref         0.2786
_refine_ls_wR_factor_gt          0.2552
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
P1 P -0.2355(6) 0.1069(4) 0.16975(19) 0.0797(12) Uani 1 1 d . . . . .
F11 F -0.1785(17) 0.2442(10) 0.1480(5) 0.137(4) Uani 1 1 d . . . . .
F12 F -0.137(2) 0.1481(13) 0.2295(6) 0.188(7) Uani 1 1 d . . . . .
F13 F -0.3914(17) 0.1366(13) 0.2002(7) 0.164(5) Uani 1 1 d . . . . .
F14 F -0.3011(14) -0.0269(10) 0.1916(5) 0.119(4) Uani 1 1 d . . . . .
F15 F -0.375(2) 0.0622(13) 0.1169(6) 0.195(7) Uani 1 1 d . . . . .
F16 F -0.104(2) 0.0685(16) 0.1367(11) 0.263(11) Uani 1 1 d . . . . .
P2 P 0.3156(5) 0.4506(4) 0.66194(16) 0.0653(10) Uani 1 1 d . . . . .
F21 F 0.4572(12) 0.4803(9) 0.6140(4) 0.110(3) Uani 1 1 d . . . . .
F22 F 0.3727(12) 0.5928(8) 0.6830(4) 0.103(3) Uani 1 1 d . . . . .
F23 F 0.4520(12) 0.4312(9) 0.7092(4) 0.100(3) Uani 1 1 d . . . . .
F24 F 0.1752(11) 0.4212(10) 0.7090(4) 0.101(3) Uani 1 1 d . . . . .
F25 F 0.2650(15) 0.3087(8) 0.6400(4) 0.117(4) Uani 1 1 d . . . . .
F26 F 0.1810(12) 0.4740(10) 0.6142(4) 0.119(4) Uani 1 1 d . . . . .
Cu1 Cu -0.13954(17) 0.07073(14) 0.49622(6) 0.0471(4) Uani 1 1 d . . . . .
N1 N -0.2306(12) 0.1457(9) 0.5656(4) 0.046(2) Uani 1 1 d . . . . .
C1 C -0.1783(18) 0.2579(14) 0.5895(7) 0.070(4) Uani 1 1 d . . . . .
H1 H -0.086294 0.315919 0.573930 0.085 Uiso 1 1 calc R U . . .
C2 C -0.259(2) 0.2941(18) 0.6394(7) 0.090(5) Uani 1 1 d . . . . .
H2 H -0.222744 0.375955 0.656147 0.107 Uiso 1 1 calc R U . . .
C3 C -0.388(2) 0.2101(18) 0.6619(6) 0.078(5) Uani 1 1 d . . . . .
H3 H -0.440282 0.235054 0.694640 0.093 Uiso 1 1 calc R U . . .
C4 C -0.4475(17) 0.0874(14) 0.6392(5) 0.057(3) Uani 1 1 d . . . . .
C5 C -0.5817(19) -0.016(2) 0.6600(7) 0.089(6) Uani 1 1 d . . . . .
H5 H -0.637367 -0.000187 0.693875 0.107 Uiso 1 1 calc R U . . .
C6 C -0.6290(18) -0.1277(18) 0.6346(6) 0.072(4) Uani 1 1 d . . . . .
H6 H -0.716972 -0.188973 0.650165 0.087 Uiso 1 1 calc R U . . .
C7 C -0.5462(14) -0.1587(13) 0.5818(5) 0.053(3) Uani 1 1 d . . . . .
C8 C -0.5883(15) -0.2730(14) 0.5516(6) 0.064(4) Uani 1 1 d . . . . .
H8 H -0.675782 -0.339090 0.564047 0.077 Uiso 1 1 calc R U . . .
C9 C -0.4984(16) -0.2894(12) 0.5017(6) 0.058(3) Uani 1 1 d . . . . .
H9 H -0.527103 -0.366709 0.480046 0.070 Uiso 1 1 calc R U . . .
C10 C -0.3680(14) -0.1925(11) 0.4843(5) 0.044(3) Uani 1 1 d . . . . .
H10 H -0.308377 -0.206556 0.451240 0.052 Uiso 1 1 calc R U . . .
N2 N -0.3230(10) -0.0812(9) 0.5119(3) 0.036(2) Uani 1 1 d . . . . .
C11 C -0.4131(13) -0.0621(11) 0.5612(5) 0.041(3) Uani 1 1 d . . . . .
C12 C -0.3614(14) 0.0577(12) 0.5888(5) 0.046(3) Uani 1 1 d . . . . .
C13 C 0.0245(13) 0.0829(12) 0.3956(5) 0.046(3) Uani 1 1 d . . . . .
C14 C 0.0613(14) 0.2081(12) 0.4197(6) 0.053(3) Uani 1 1 d . . . . .
C15 C 0.1585(17) 0.3023(14) 0.3844(7) 0.075(4) Uani 1 1 d . . . . .
H15 H 0.185225 0.385247 0.398816 0.091 Uiso 1 1 calc R U . . .
C16 C 0.212(2) 0.2738(19) 0.3312(8) 0.095(6) Uani 1 1 d . . . . .
H16 H 0.278601 0.337023 0.309726 0.114 Uiso 1 1 calc R U . . .
O17 O 0.1716(11) 0.1566(12) 0.3084(4) 0.078(3) Uani 1 1 d . . . . .
C18 C 0.0745(15) 0.0578(14) 0.3391(5) 0.061(4) Uani 1 1 d . . . . .
C19 C 0.0294(18) -0.0653(15) 0.3045(6) 0.075(4) Uani 1 1 d . . . . .
H19A H -0.011639 -0.129638 0.331313 0.113 Uiso 1 1 calc R U . . .
H19B H 0.129806 -0.074816 0.286273 0.113 Uiso 1 1 calc R U . . .
H19C H -0.059113 -0.071207 0.273633 0.113 Uiso 1 1 calc R U . . .
O20 O -0.0584(9) -0.0059(7) 0.4296(3) 0.0432(18) Uani 1 1 d . . . . .
O21 O 0.0016(10) 0.2268(8) 0.4707(4) 0.059(2) Uani 1 1 d . . . . .
Cu2 Cu 0.85825(19) 0.56904(16) 1.00091(6) 0.0566(5) Uani 1 1 d . . . . .
N22 N 0.7306(13) 0.6077(11) 0.9312(4) 0.055(3) Uani 1 1 d . . . . .
C23 C 0.7664(18) 0.7093(14) 0.9024(6) 0.064(4) Uani 1 1 d . . . . .
H23 H 0.865134 0.774424 0.915141 0.077 Uiso 1 1 calc R U . . .
C24 C 0.662(2) 0.7241(17) 0.8531(7) 0.086(5) Uani 1 1 d . . . . .
H24 H 0.687925 0.797543 0.833848 0.103 Uiso 1 1 calc R U . . .
C25 C 0.516(2) 0.6213(18) 0.8344(6) 0.078(5) Uani 1 1 d . . . . .
H25 H 0.442449 0.627928 0.802544 0.094 Uiso 1 1 calc R U . . .
C26 C 0.4795(16) 0.5127(15) 0.8618(5) 0.058(4) Uani 1 1 d . . . . .
C27 C 0.3401(18) 0.4047(18) 0.8459(6) 0.080(5) Uani 1 1 d . . . . .
H27 H 0.264550 0.404117 0.813316 0.096 Uiso 1 1 calc R U . . .
C28 C 0.3129(16) 0.3041(17) 0.8759(6) 0.075(5) Uani 1 1 d . . . . .
H28 H 0.218270 0.235657 0.863319 0.090 Uiso 1 1 calc R U . . .
C29 C 0.4213(15) 0.2948(14) 0.9266(6) 0.058(3) Uani 1 1 d . . . . .
C30 C 0.4016(17) 0.1955(14) 0.9605(7) 0.068(4) Uani 1 1 d . . . . .
H30 H 0.310765 0.123033 0.950567 0.081 Uiso 1 1 calc R U . . .
C31 C 0.5122(18) 0.2014(16) 1.0082(6) 0.071(4) Uani 1 1 d . . . . .
H31 H 0.498279 0.133413 1.030964 0.085 Uiso 1 1 calc R U . . .
C32 C 0.6473(17) 0.3101(13) 1.0230(5) 0.057(3) Uani 1 1 d . . . . .
H32 H 0.723266 0.313571 1.055858 0.068 Uiso 1 1 calc R U . . .
N33 N 0.6710(11) 0.4085(9) 0.9918(4) 0.042(2) Uani 1 1 d . . . . .
C34 C 0.5591(15) 0.4031(13) 0.9438(5) 0.053(3) Uani 1 1 d . . . . .
C35 C 0.5896(15) 0.5084(14) 0.9123(5) 0.055(3) Uani 1 1 d . . . . .
C36 C 1.0685(14) 0.6324(14) 1.0993(5) 0.054(3) Uani 1 1 d . . . . .
C37 C 1.0847(15) 0.7448(14) 1.0713(6) 0.062(4) Uani 1 1 d . . . . .
C38 C 1.1955(19) 0.8554(15) 1.1036(7) 0.078(4) Uani 1 1 d . . . . .
H38 H 1.221953 0.930694 1.085991 0.093 Uiso 1 1 calc R U . . .
C39 C 1.2599(19) 0.8503(18) 1.1582(10) 0.097(6) Uani 1 1 d . . . . .
H39 H 1.323112 0.924562 1.179579 0.116 Uiso 1 1 calc R U . . .
O40 O 1.2399(12) 0.7445(12) 1.1848(4) 0.077(3) Uani 1 1 d . . . . .
C41 C 1.1406(14) 0.6359(13) 1.1569(5) 0.056(3) Uani 1 1 d . . . . .
C42 C 1.1212(19) 0.5289(15) 1.1938(6) 0.078(4) Uani 1 1 d . . . . .
H42A H 1.230137 0.535692 1.214245 0.116 Uiso 1 1 calc R U . . .
H42B H 1.083186 0.452972 1.168129 0.116 Uiso 1 1 calc R U . . .
H42C H 1.037647 0.528484 1.223072 0.116 Uiso 1 1 calc R U . . .
O43 O 0.9741(10) 0.5259(8) 1.0694(3) 0.056(2) Uani 1 1 d . . . . .
O44 O 1.0055(11) 0.7376(8) 1.0203(4) 0.061(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
P1 F16 1.480(14) . ?
P1 F12 1.495(11) . ?
P1 F15 1.546(13) . ?
P1 F14 1.563(10) . ?
P1 F13 1.578(13) . ?
P1 F11 1.595(10) . ?
P2 F24 1.558(8) . ?
P2 F22 1.568(9) . ?
P2 F25 1.572(9) . ?
P2 F23 1.573(9) . ?
P2 F21 1.579(9) . ?
P2 F26 1.588(10) . ?
Cu1 O20 1.910(7) . ?
Cu1 O21 1.928(9) . ?
Cu1 N2 1.969(9) . ?
Cu1 N1 1.990(9) . ?
N1 C1 1.282(16) . ?
N1 C12 1.366(15) . ?
C1 C2 1.41(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.32(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C4 C12 1.421(15) . ?
C4 C5 1.45(2) . ?
C5 C6 1.29(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.453(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(18) . ?
C7 C11 1.403(15) . ?
C8 C9 1.386(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(16) . ?
C9 H9 0.9300 . ?
C10 N2 1.303(13) . ?
C10 H10 0.9300 . ?
N2 C11 1.386(13) . ?
C11 C12 1.386(16) . ?
C13 O20 1.329(12) . ?
C13 C18 1.376(16) . ?
C13 C14 1.420(17) . ?
C14 O21 1.284(14) . ?
C14 C15 1.423(17) . ?
C15 C16 1.33(2) . ?
C15 H15 0.9300 . ?
C16 O17 1.33(2) . ?
C16 H16 0.9300 . ?
O17 C18 1.396(15) . ?
C18 C19 1.482(19) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cu2 O43 1.926(7) . ?
Cu2 O44 1.931(9) . ?
Cu2 N22 1.977(10) . ?
Cu2 N33 1.979(10) . ?
N22 C23 1.313(16) . ?
N22 C35 1.370(16) . ?
C23 C24 1.411(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.42(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.36(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.41(2) . ?
C26 C35 1.421(15) . ?
C27 C28 1.32(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.434(18) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(19) . ?
C29 C34 1.406(18) . ?
C30 C31 1.349(18) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(19) . ?
C31 H31 0.9300 . ?
C32 N33 1.319(15) . ?
C32 H32 0.9300 . ?
N33 C34 1.362(13) . ?
C34 C35 1.385(18) . ?
C36 O43 1.334(14) . ?
C36 C41 1.380(16) . ?
C36 C37 1.426(18) . ?
C37 O44 1.267(15) . ?
C37 C38 1.429(19) . ?
C38 C39 1.31(2) . ?
C38 H38 0.9300 . ?
C39 O40 1.34(2) . ?
C39 H39 0.9300 . ?
O40 C41 1.345(15) . ?
C41 C42 1.480(19) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F16 P1 F12 98.8(12) . . ?
F16 P1 F15 93.9(12) . . ?
F12 P1 F15 166.5(11) . . ?
F16 P1 F14 88.6(8) . . ?
F12 P1 F14 88.0(7) . . ?
F15 P1 F14 87.7(7) . . ?
F16 P1 F13 173.6(12) . . ?
F12 P1 F13 86.9(9) . . ?
F15 P1 F13 80.2(9) . . ?
F14 P1 F13 88.6(7) . . ?
F16 P1 F11 94.2(8) . . ?
F12 P1 F11 92.8(8) . . ?
F15 P1 F11 90.9(7) . . ?
F14 P1 F11 176.9(7) . . ?
F13 P1 F11 88.5(7) . . ?
F24 P2 F22 91.6(6) . . ?
F24 P2 F25 90.2(6) . . ?
F22 P2 F25 178.0(6) . . ?
F24 P2 F23 90.6(5) . . ?
F22 P2 F23 90.1(5) . . ?
F25 P2 F23 89.0(6) . . ?
F24 P2 F21 179.7(6) . . ?
F22 P2 F21 88.5(6) . . ?
F25 P2 F21 89.6(5) . . ?
F23 P2 F21 89.7(6) . . ?
F24 P2 F26 90.1(5) . . ?
F22 P2 F26 88.5(6) . . ?
F25 P2 F26 92.3(6) . . ?
F23 P2 F26 178.5(6) . . ?
F21 P2 F26 89.6(6) . . ?
O20 Cu1 O21 86.3(3) . . ?
O20 Cu1 N2 94.6(3) . . ?
O21 Cu1 N2 167.8(3) . . ?
O20 Cu1 N1 178.2(4) . . ?
O21 Cu1 N1 95.4(4) . . ?
N2 Cu1 N1 83.6(4) . . ?
C1 N1 C12 120.9(12) . . ?
C1 N1 Cu1 128.7(10) . . ?
C12 N1 Cu1 110.4(8) . . ?
N1 C1 C2 120.5(15) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.2(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 123.2(14) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C12 114.7(14) . . ?
C3 C4 C5 129.7(14) . . ?
C12 C4 C5 115.6(13) . . ?
C6 C5 C4 124.5(14) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C5 C6 C7 120.6(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C11 118.4(11) . . ?
C8 C7 C6 125.0(13) . . ?
C11 C7 C6 116.7(13) . . ?
C7 C8 C9 118.9(12) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 120.2(12) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C10 C9 123.2(11) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 N2 C11 117.6(9) . . ?
C10 N2 Cu1 130.6(7) . . ?
C11 N2 Cu1 111.9(7) . . ?
C12 C11 N2 115.5(10) . . ?
C12 C11 C7 122.7(11) . . ?
N2 C11 C7 121.8(11) . . ?
N1 C12 C11 118.6(10) . . ?
N1 C12 C4 121.4(12) . . ?
C11 C12 C4 119.9(12) . . ?
O20 C13 C18 122.7(12) . . ?
O20 C13 C14 117.4(10) . . ?
C18 C13 C14 119.8(12) . . ?
O21 C14 C13 117.4(10) . . ?
O21 C14 C15 125.6(13) . . ?
C13 C14 C15 117.0(13) . . ?
C16 C15 C14 121.3(16) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
O17 C16 C15 121.0(14) . . ?
O17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 O17 C18 122.1(12) . . ?
C13 C18 O17 118.6(13) . . ?
C13 C18 C19 126.8(12) . . ?
O17 C18 C19 114.5(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 O20 Cu1 108.0(7) . . ?
C14 O21 Cu1 109.6(8) . . ?
O43 Cu2 O44 86.6(4) . . ?
O43 Cu2 N22 177.6(4) . . ?
O44 Cu2 N22 95.4(4) . . ?
O43 Cu2 N33 94.4(4) . . ?
O44 Cu2 N33 167.3(3) . . ?
N22 Cu2 N33 83.4(4) . . ?
C23 N22 C35 120.0(11) . . ?
C23 N22 Cu2 129.2(10) . . ?
C35 N22 Cu2 110.8(8) . . ?
N22 C23 C24 123.0(15) . . ?
N22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C23 C24 C25 116.4(15) . . ?
C23 C24 H24 121.8 . . ?
C25 C24 H24 121.8 . . ?
C26 C25 C24 121.9(13) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 126.3(13) . . ?
C25 C26 C35 117.3(14) . . ?
C27 C26 C35 116.4(14) . . ?
C28 C27 C26 122.1(14) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 123.6(15) . . ?
C27 C28 H28 118.2 . . ?
C29 C28 H28 118.2 . . ?
C30 C29 C34 117.6(12) . . ?
C30 C29 C28 127.4(14) . . ?
C34 C29 C28 114.9(14) . . ?
C31 C30 C29 120.8(14) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 119.4(14) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
N33 C32 C31 122.0(12) . . ?
N33 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C32 N33 C34 118.8(11) . . ?
C32 N33 Cu2 129.7(8) . . ?
C34 N33 Cu2 111.5(9) . . ?
N33 C34 C35 116.7(12) . . ?
N33 C34 C29 121.4(13) . . ?
C35 C34 C29 121.9(11) . . ?
N22 C35 C34 117.6(10) . . ?
N22 C35 C26 121.3(13) . . ?
C34 C35 C26 121.1(13) . . ?
O43 C36 C41 121.8(13) . . ?
O43 C36 C37 117.8(11) . . ?
C41 C36 C37 120.4(13) . . ?
O44 C37 C36 118.1(12) . . ?
O44 C37 C38 126.4(15) . . ?
C36 C37 C38 115.5(13) . . ?
C39 C38 C37 119.8(17) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 O40 123.9(15) . . ?
C38 C39 H39 118.0 . . ?
O40 C39 H39 118.0 . . ?
C39 O40 C41 119.9(12) . . ?
O40 C41 C36 120.0(13) . . ?
O40 C41 C42 113.5(11) . . ?
C36 C41 C42 126.5(13) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C36 O43 Cu2 106.9(8) . . ?
C37 O44 Cu2 109.2(9) . . ?

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
C12 N1 C1 C2 -2.3(17) . . . . ?
Cu1 N1 C1 C2 -179.6(9) . . . . ?
N1 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C12 -0.7(19) . . . . ?
C2 C3 C4 C5 177.7(14) . . . . ?
C3 C4 C5 C6 179.1(14) . . . . ?
C12 C4 C5 C6 -3(2) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C5 C6 C7 C8 -179.1(14) . . . . ?
C5 C6 C7 C11 0.8(19) . . . . ?
C11 C7 C8 C9 -0.1(17) . . . . ?
C6 C7 C8 C9 179.9(11) . . . . ?
C7 C8 C9 C10 1.2(18) . . . . ?
C8 C9 C10 N2 -1.3(17) . . . . ?
C9 C10 N2 C11 0.2(15) . . . . ?
C9 C10 N2 Cu1 179.0(8) . . . . ?
C10 N2 C11 C12 -179.6(9) . . . . ?
Cu1 N2 C11 C12 1.3(10) . . . . ?
C10 N2 C11 C7 1.0(13) . . . . ?
Cu1 N2 C11 C7 -178.0(8) . . . . ?
C8 C7 C11 C12 179.7(10) . . . . ?
C6 C7 C11 C12 -0.3(15) . . . . ?
C8 C7 C11 N2 -1.0(15) . . . . ?
C6 C7 C11 N2 179.0(9) . . . . ?
C1 N1 C12 C11 179.9(10) . . . . ?
Cu1 N1 C12 C11 -2.3(11) . . . . ?
C1 N1 C12 C4 1.7(15) . . . . ?
Cu1 N1 C12 C4 179.5(7) . . . . ?
N2 C11 C12 N1 0.7(13) . . . . ?
C7 C11 C12 N1 -180.0(9) . . . . ?
N2 C11 C12 C4 178.9(8) . . . . ?
C7 C11 C12 C4 -1.7(15) . . . . ?
C3 C4 C12 N1 -0.2(15) . . . . ?
C5 C4 C12 N1 -178.8(10) . . . . ?
C3 C4 C12 C11 -178.4(10) . . . . ?
C5 C4 C12 C11 3.0(14) . . . . ?
O20 C13 C14 O21 -4.7(14) . . . . ?
C18 C13 C14 O21 175.3(10) . . . . ?
O20 C13 C14 C15 176.6(10) . . . . ?
C18 C13 C14 C15 -3.5(16) . . . . ?
O21 C14 C15 C16 -178.5(13) . . . . ?
C13 C14 C15 C16 0.1(19) . . . . ?
C14 C15 C16 O17 2(2) . . . . ?
C15 C16 O17 C18 -1(2) . . . . ?
O20 C13 C18 O17 -175.5(9) . . . . ?
C14 C13 C18 O17 4.5(15) . . . . ?
O20 C13 C18 C19 7.5(18) . . . . ?
C14 C13 C18 C19 -172.5(11) . . . . ?
C16 O17 C18 C13 -2.3(17) . . . . ?
C16 O17 C18 C19 175.1(12) . . . . ?
C18 C13 O20 Cu1 -169.1(8) . . . . ?
C14 C13 O20 Cu1 10.8(10) . . . . ?
C13 C14 O21 Cu1 -4.3(12) . . . . ?
C15 C14 O21 Cu1 174.4(10) . . . . ?
C35 N22 C23 C24 2.3(18) . . . . ?
Cu2 N22 C23 C24 -179.7(9) . . . . ?
N22 C23 C24 C25 -2(2) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C24 C25 C26 C27 -178.7(13) . . . . ?
C24 C25 C26 C35 3.2(18) . . . . ?
C25 C26 C27 C28 -178.6(13) . . . . ?
C35 C26 C27 C28 -0.5(19) . . . . ?
C26 C27 C28 C29 0(2) . . . . ?
C27 C28 C29 C30 179.1(14) . . . . ?
C27 C28 C29 C34 1.5(19) . . . . ?
C34 C29 C30 C31 -0.8(18) . . . . ?
C28 C29 C30 C31 -178.3(12) . . . . ?
C29 C30 C31 C32 0.2(19) . . . . ?
C30 C31 C32 N33 0.1(19) . . . . ?
C31 C32 N33 C34 0.2(16) . . . . ?
C31 C32 N33 Cu2 -176.4(9) . . . . ?
C32 N33 C34 C35 -179.8(9) . . . . ?
Cu2 N33 C34 C35 -2.7(11) . . . . ?
C32 N33 C34 C29 -0.7(15) . . . . ?
Cu2 N33 C34 C29 176.4(8) . . . . ?
C30 C29 C34 N33 1.0(16) . . . . ?
C28 C29 C34 N33 178.9(10) . . . . ?
C30 C29 C34 C35 -180.0(11) . . . . ?
C28 C29 C34 C35 -2.1(16) . . . . ?
C23 N22 C35 C34 179.1(10) . . . . ?
Cu2 N22 C35 C34 0.8(12) . . . . ?
C23 N22 C35 C26 -0.2(16) . . . . ?
Cu2 N22 C35 C26 -178.5(8) . . . . ?
N33 C34 C35 N22 1.2(14) . . . . ?
C29 C34 C35 N22 -177.8(10) . . . . ?
N33 C34 C35 C26 -179.4(9) . . . . ?
C29 C34 C35 C26 1.5(16) . . . . ?
C25 C26 C35 N22 -2.6(16) . . . . ?
C27 C26 C35 N22 179.2(10) . . . . ?
C25 C26 C35 C34 178.2(11) . . . . ?
C27 C26 C35 C34 -0.1(16) . . . . ?
O43 C36 C37 O44 1.6(15) . . . . ?
C41 C36 C37 O44 -174.8(10) . . . . ?
O43 C36 C37 C38 -176.4(10) . . . . ?
C41 C36 C37 C38 7.2(16) . . . . ?
O44 C37 C38 C39 175.3(13) . . . . ?
C36 C37 C38 C39 -7.0(19) . . . . ?
C37 C38 C39 O40 6(2) . . . . ?
C38 C39 O40 C41 -4(2) . . . . ?
C39 O40 C41 C36 4.2(17) . . . . ?
C39 O40 C41 C42 -175.8(12) . . . . ?
O43 C36 C41 O40 177.7(9) . . . . ?
C37 C36 C41 O40 -6.0(16) . . . . ?
O43 C36 C41 C42 -2.3(18) . . . . ?
C37 C36 C41 C42 174.0(11) . . . . ?
C41 C36 O43 Cu2 166.9(8) . . . . ?
C37 C36 O43 Cu2 -9.5(11) . . . . ?
C36 C37 O44 Cu2 7.3(12) . . . . ?
C38 C37 O44 Cu2 -174.9(10) . . . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.119

