# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_C_JE_002
_database_code_depnum_ccdc_archive 'CCDC 2263164'
loop_
_audit_author_name
_audit_author_address
'Bruno Donnadieu'
;Mississippi State University
United States of America
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cu F6 N4 O2 P'
_chemical_formula_sum            'C17 H17 Cu F6 N4 O2 P'
_chemical_formula_weight         517.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.0314(3)
_cell_length_b                   17.4564(4)
_cell_length_c                   9.0216(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.6770(14)
_cell_angle_gamma                90
_cell_volume                     1994.05(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1866
_cell_measurement_theta_min      3.490
_cell_measurement_theta_max      74.489

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    3.045
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture  '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23796
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.490
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4057
_reflns_number_gt                3172
_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       'APEX4 v2021.4.0'
_computing_cell_refinement       'APEX4 v2021 4.0'
_computing_data_reduction        'Saint, APEX v2021.4.0.'
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXTL-2018/3
_computing_molecular_graphics    'Mercury V.4.2.0,POV-Ray v 3.7'
_computing_publication_material  'APEX3 v202.4.0'
_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)+8.2561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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 0.18235(4) 0.28742(3) 0.67082(6) 0.01493(14) Uani 1 1 d . . . . .
N1 N 0.0410(2) 0.33250(18) 0.5469(3) 0.0175(7) Uani 1 1 d . . . . .
N2 N 0.2175(3) 0.43563(18) 0.5398(3) 0.0167(7) Uani 1 1 d . . . . .
N3 N 0.3315(3) 0.24787(19) 0.7925(4) 0.0186(7) Uani 1 1 d . . . . .
N4 N 0.3335(2) 0.41344(18) 0.7458(4) 0.0179(7) Uani 1 1 d . . . . .
C1 C -0.0476(3) 0.2961(2) 0.5619(5) 0.0203(8) Uani 1 1 d . . . . .
H1 H -0.042762 0.260966 0.643704 0.024 Uiso 1 1 calc R U . . .
C2 C -0.1444(3) 0.3079(2) 0.4635(5) 0.0254(9) Uani 1 1 d . . . . .
H2 H -0.204976 0.280732 0.476133 0.030 Uiso 1 1 calc R U . . .
C3 C -0.1519(3) 0.3599(3) 0.3461(5) 0.0272(9) Uani 1 1 d . . . . .
H3 H -0.217291 0.367998 0.274509 0.033 Uiso 1 1 calc R U . . .
C4 C -0.0631(3) 0.3998(2) 0.3345(5) 0.0232(9) Uani 1 1 d . . . . .
H4 H -0.067567 0.437415 0.257198 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0331(3) 0.3851(2) 0.4357(4) 0.0170(8) Uani 1 1 d . . . . .
C6 C 0.1298(3) 0.4247(2) 0.4073(4) 0.0191(8) Uani 1 1 d . . . . .
H6A H 0.155746 0.394679 0.330531 0.023 Uiso 1 1 calc R U . . .
H6B H 0.108190 0.475606 0.362140 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2882(3) 0.4959(2) 0.5590(5) 0.0204(8) Uani 1 1 d . . . . .
H7 H 0.286090 0.538524 0.492760 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3611(3) 0.4824(2) 0.6903(5) 0.0227(9) Uani 1 1 d . . . . .
H8 H 0.419617 0.513933 0.735350 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2460(3) 0.3853(2) 0.6543(4) 0.0178(8) Uani 1 1 d . . . . .
C10 C 0.3836(3) 0.3784(2) 0.8918(4) 0.0234(9) Uani 1 1 d . . . . .
H10A H 0.338636 0.387889 0.964375 0.028 Uiso 1 1 calc R U . . .
H10B H 0.452215 0.404039 0.932676 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4024(3) 0.2930(2) 0.8846(4) 0.0201(8) Uani 1 1 d . . . . .
C12 C 0.4915(3) 0.2629(3) 0.9836(5) 0.0291(10) Uani 1 1 d . . . . .
H12 H 0.540185 0.295894 1.048640 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5087(4) 0.1849(3) 0.9870(6) 0.0357(11) Uani 1 1 d . . . . .
H13 H 0.568785 0.163516 1.055115 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4378(3) 0.1387(3) 0.8905(5) 0.0300(10) Uani 1 1 d . . . . .
H14 H 0.448379 0.084893 0.890072 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3504(3) 0.1717(2) 0.7937(5) 0.0214(8) Uani 1 1 d . . . . .
H15 H 0.302068 0.139683 0.725722 0.026 Uiso 1 1 calc R U . . .
O1 O 0.1252(2) 0.18312(14) 0.6229(3) 0.0166(5) Uani 1 1 d . . . . .
O2 O 0.1438(2) 0.21544(16) 0.3936(3) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.1124(3) 0.1693(2) 0.4800(4) 0.0161(8) Uani 1 1 d . . . . .
C17 C 0.0559(3) 0.0973(2) 0.4195(5) 0.0225(8) Uani 1 1 d . . . . .
H17A H -0.020429 0.106752 0.392658 0.034 Uiso 1 1 calc R U . . .
H17B H 0.072274 0.057247 0.497551 0.034 Uiso 1 1 calc R U . . .
H17C H 0.078658 0.080776 0.328519 0.034 Uiso 1 1 calc R U . . .
P1 P 0.70589(8) 0.42517(6) 0.87247(12) 0.0235(2) Uani 1 1 d . . . . .
F1 F 0.6039(2) 0.44425(18) 0.7386(4) 0.0486(8) Uani 1 1 d . . . . .
F2 F 0.6397(3) 0.4436(2) 0.9958(4) 0.0592(10) Uani 1 1 d . . . . .
F3 F 0.8071(2) 0.4058(2) 1.0014(3) 0.0585(9) Uani 1 1 d . . . . .
F4 F 0.7705(2) 0.40664(19) 0.7471(3) 0.0474(8) Uani 1 1 d . . . . .
F5 F 0.7399(3) 0.51221(18) 0.8692(5) 0.0651(10) Uani 1 1 d . . . . .
F6 F 0.6688(3) 0.33882(17) 0.8676(4) 0.0556(9) 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 C9 1.920(4) . ?
Cu1 O1 1.976(3) . ?
Cu1 N1 2.071(3) . ?
Cu1 N3 2.109(3) . ?
Cu1 O2 2.184(2) 4_566 ?
N1 C5 1.346(5) . ?
N1 C1 1.352(5) . ?
N2 C9 1.340(5) . ?
N2 C7 1.383(5) . ?
N2 C6 1.457(5) . ?
N3 C11 1.342(5) . ?
N3 C15 1.351(5) . ?
N4 C9 1.333(5) . ?
N4 C8 1.384(5) . ?
N4 C10 1.459(5) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.512(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.352(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.516(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.390(6) . ?
C12 C13 1.379(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O1 C16 1.283(4) . ?
O2 C16 1.254(4) . ?
C16 C17 1.493(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
P1 F3 1.576(3) . ?
P1 F6 1.580(3) . ?
P1 F5 1.585(3) . ?
P1 F2 1.594(3) . ?
P1 F4 1.594(3) . ?
P1 F1 1.605(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
C9 Cu1 O1 161.83(13) . . ?
C9 Cu1 N1 88.03(15) . . ?
O1 Cu1 N1 89.46(12) . . ?
C9 Cu1 N3 88.26(15) . . ?
O1 Cu1 N3 93.77(12) . . ?
N1 Cu1 N3 176.17(13) . . ?
C9 Cu1 O2 106.82(13) . 4_566 ?
O1 Cu1 O2 91.34(10) . 4_566 ?
N1 Cu1 O2 97.85(11) . 4_566 ?
N3 Cu1 O2 84.14(11) . 4_566 ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Cu1 124.3(3) . . ?
C1 N1 Cu1 116.0(3) . . ?
C9 N2 C7 110.3(3) . . ?
C9 N2 C6 124.6(3) . . ?
C7 N2 C6 124.9(3) . . ?
C11 N3 C15 118.3(4) . . ?
C11 N3 Cu1 123.0(3) . . ?
C15 N3 Cu1 118.0(3) . . ?
C9 N4 C8 110.8(3) . . ?
C9 N4 C10 122.6(3) . . ?
C8 N4 C10 126.3(3) . . ?
N1 C1 C2 122.6(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.9(4) . . ?
N1 C5 C6 121.2(3) . . ?
C4 C5 C6 117.6(3) . . ?
N2 C6 C5 116.4(3) . . ?
N2 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
N2 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C8 C7 N2 106.6(3) . . ?
C8 C7 H7 126.7 . . ?
N2 C7 H7 126.7 . . ?
C7 C8 N4 106.2(3) . . ?
C7 C8 H8 126.9 . . ?
N4 C8 H8 126.9 . . ?
N4 C9 N2 106.0(3) . . ?
N4 C9 Cu1 127.0(3) . . ?
N2 C9 Cu1 126.7(3) . . ?
N4 C10 C11 114.6(3) . . ?
N4 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N4 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N3 C11 C12 121.7(4) . . ?
N3 C11 C10 120.6(3) . . ?
C12 C11 C10 117.6(4) . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 122.3(4) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C16 O1 Cu1 110.2(2) . . ?
C16 O2 Cu1 137.5(2) . 4_565 ?
O2 C16 O1 121.3(3) . . ?
O2 C16 C17 121.2(3) . . ?
O1 C16 C17 117.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F3 P1 F6 90.7(2) . . ?
F3 P1 F5 91.8(2) . . ?
F6 P1 F5 177.3(2) . . ?
F3 P1 F2 91.40(19) . . ?
F6 P1 F2 89.98(19) . . ?
F5 P1 F2 91.1(2) . . ?
F3 P1 F4 89.43(17) . . ?
F6 P1 F4 89.76(18) . . ?
F5 P1 F4 89.10(19) . . ?
F2 P1 F4 179.13(18) . . ?
F3 P1 F1 178.86(19) . . ?
F6 P1 F1 89.08(18) . . ?
F5 P1 F1 88.42(19) . . ?
F2 P1 F1 89.72(18) . . ?
F4 P1 F1 89.45(16) . . ?

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
C5 N1 C1 C2 3.3(6) . . . . ?
Cu1 N1 C1 C2 -165.2(3) . . . . ?
N1 C1 C2 C3 -1.1(6) . . . . ?
C1 C2 C3 C4 -2.0(6) . . . . ?
C2 C3 C4 C5 2.8(6) . . . . ?
C1 N1 C5 C4 -2.5(5) . . . . ?
Cu1 N1 C5 C4 165.0(3) . . . . ?
C1 N1 C5 C6 -176.6(3) . . . . ?
Cu1 N1 C5 C6 -9.1(5) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
C3 C4 C5 C6 173.8(4) . . . . ?
C9 N2 C6 C5 36.7(5) . . . . ?
C7 N2 C6 C5 -149.2(3) . . . . ?
N1 C5 C6 N2 -30.6(5) . . . . ?
C4 C5 C6 N2 155.0(3) . . . . ?
C9 N2 C7 C8 -0.9(4) . . . . ?
C6 N2 C7 C8 -175.8(3) . . . . ?
N2 C7 C8 N4 1.0(4) . . . . ?
C9 N4 C8 C7 -0.8(4) . . . . ?
C10 N4 C8 C7 -174.4(3) . . . . ?
C8 N4 C9 N2 0.2(4) . . . . ?
C10 N4 C9 N2 174.1(3) . . . . ?
C8 N4 C9 Cu1 174.2(3) . . . . ?
C10 N4 C9 Cu1 -12.0(5) . . . . ?
C7 N2 C9 N4 0.4(4) . . . . ?
C6 N2 C9 N4 175.3(3) . . . . ?
C7 N2 C9 Cu1 -173.5(3) . . . . ?
C6 N2 C9 Cu1 1.3(5) . . . . ?
C9 N4 C10 C11 50.2(5) . . . . ?
C8 N4 C10 C11 -137.0(4) . . . . ?
C15 N3 C11 C12 -2.4(5) . . . . ?
Cu1 N3 C11 C12 168.4(3) . . . . ?
C15 N3 C11 C10 -178.0(3) . . . . ?
Cu1 N3 C11 C10 -7.3(5) . . . . ?
N4 C10 C11 N3 -37.5(5) . . . . ?
N4 C10 C11 C12 146.7(4) . . . . ?
N3 C11 C12 C13 0.7(6) . . . . ?
C10 C11 C12 C13 176.5(4) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C11 N3 C15 C14 2.6(6) . . . . ?
Cu1 N3 C15 C14 -168.6(3) . . . . ?
C13 C14 C15 N3 -1.1(6) . . . . ?
Cu1 O2 C16 O1 159.8(3) 4_565 . . . ?
Cu1 O2 C16 C17 -22.0(6) 4_565 . . . ?
Cu1 O1 C16 O2 6.5(4) . . . . ?
Cu1 O1 C16 C17 -171.7(3) . . . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.095



####################################################################### 
# 
# 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_cu_c_jm_001
_database_code_depnum_ccdc_archive 'CCDC 2263165'
loop_
_audit_author_name
_audit_author_address
'Bruno Donnadieu'
;Mississippi State University
United States of America
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 Cu F6 N4 O3 P'
_chemical_formula_sum            'C24 H27 Cu F6 N4 O3 P'
_chemical_formula_weight         628.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   9.4890(14)
_cell_length_b                   10.9068(16)
_cell_length_c                   14.481(2)
_cell_angle_alpha                111.242(6)
_cell_angle_beta                 103.332(6)
_cell_angle_gamma                96.766(5)
_cell_volume                     1325.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1302
_cell_measurement_theta_min      3.427
_cell_measurement_theta_max      68.241

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             642
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    2.432
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture  '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29336
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.427
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4812
_reflns_number_gt                4349
_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       'APEX4 v2021.4.0'
_computing_cell_refinement       'APEX4 v2021.4.0'
_computing_data_reduction        'Saint, APEX4 v2021.4.0.'
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXTL-2018/3
_computing_molecular_graphics    'Mercury V.4.2.0,POV-Ray v 3.7'
_computing_publication_material  'APEX4 v2021.4.0'
_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)+(0.0322P)²+1.3940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4812
_refine_ls_number_parameters     474
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

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 0.50974(4) 0.23824(3) 0.15753(2) 0.03451(13) Uani 1 1 d . . . . .
N1 N 0.6944(2) 0.1813(2) 0.22635(15) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.3143(2) 0.2917(2) 0.09503(15) 0.0399(5) Uani 1 1 d . . . . .
N3 N 0.4834(2) 0.22838(19) 0.35155(14) 0.0325(4) Uani 1 1 d . . . . .
N4 N 0.3756(2) 0.37723(19) 0.31818(15) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.8188(3) 0.1983(3) 0.1989(2) 0.0436(6) Uani 1 1 d . . . . .
H1 H 0.815725 0.228129 0.144572 0.052 Uiso 1 1 calc R U . . .
C2 C 0.9504(3) 0.1748(3) 0.2455(2) 0.0510(7) Uani 1 1 d . . . . .
H2 H 1.035560 0.187587 0.223254 0.061 Uiso 1 1 calc R U . . .
C3 C 0.9566(3) 0.1328(3) 0.3243(2) 0.0539(7) Uani 1 1 d . . . . .
H3 H 1.045944 0.115506 0.357577 0.065 Uiso 1 1 calc R U . . .
C4 C 0.8294(3) 0.1160(3) 0.3547(2) 0.0470(6) Uani 1 1 d . . . . .
H4 H 0.831324 0.087530 0.409589 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6999(3) 0.1410(2) 0.30461(18) 0.0360(5) Uani 1 1 d . . . . .
C6 C 0.5609(3) 0.1169(2) 0.33583(19) 0.0383(5) Uani 1 1 d . . . . .
H6A H 0.492136 0.033353 0.281404 0.046 Uiso 1 1 calc R U . . .
H6B H 0.588097 0.102720 0.400846 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4585(3) 0.2883(2) 0.28538(17) 0.0326(5) Uani 1 1 d . . . . .
C8 C 0.3430(2) 0.3734(2) 0.40657(17) 0.0315(5) Uani 1 1 d . . . . .
C9 C 0.2604(3) 0.4416(2) 0.46775(18) 0.0353(5) Uani 1 1 d . . . . .
H9 H 0.216753 0.510022 0.454670 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2435(3) 0.4071(2) 0.54832(18) 0.0367(5) Uani 1 1 d . . . . .
C11 C 0.3128(3) 0.3077(2) 0.56906(18) 0.0366(5) Uani 1 1 d . . . . .
C12 C 0.3985(3) 0.2431(2) 0.50923(18) 0.0345(5) Uani 1 1 d . . . . .
H12 H 0.446734 0.177797 0.523775 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4116(2) 0.2768(2) 0.42772(17) 0.0309(5) Uani 1 1 d . . . . .
C14 C 0.3282(3) 0.4626(2) 0.26427(19) 0.0401(6) Uani 1 1 d . . . . .
H14A H 0.416338 0.527726 0.271599 0.048 Uiso 1 1 calc R U . . .
H14B H 0.261389 0.514614 0.297266 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2488(3) 0.3819(2) 0.15093(19) 0.0373(5) Uani 1 1 d . . . . .
C16 C 0.1154(3) 0.4059(3) 0.1055(2) 0.0491(7) Uani 1 1 d . . . . .
H16 H 0.069622 0.468709 0.146340 0.059 Uiso 1 1 calc R U . . .
C17 C 0.0501(3) 0.3366(3) -0.0004(3) 0.0622(8) Uani 1 1 d . . . . .
H17 H -0.040442 0.352616 -0.033256 0.075 Uiso 1 1 calc R U . . .
C18 C 0.1168(3) 0.2452(3) -0.0572(2) 0.0610(8) Uani 1 1 d . . . . .
H18 H 0.073477 0.197275 -0.129951 0.073 Uiso 1 1 calc R U . . .
C19 C 0.2475(3) 0.2236(3) -0.0076(2) 0.0515(7) Uani 1 1 d . . . . .
H19 H 0.292310 0.158406 -0.047079 0.062 Uiso 1 1 calc R U . . .
C20 C 0.1473(3) 0.4739(3) 0.6126(2) 0.0514(7) Uani 1 1 d . . . . .
H20A H 0.114160 0.544037 0.591379 0.077 Uiso 1 1 calc R U . . .
H20B H 0.204836 0.514763 0.686087 0.077 Uiso 1 1 calc R U . . .
H20C H 0.060700 0.406268 0.601931 0.077 Uiso 1 1 calc R U . . .
C21 C 0.2924(3) 0.2687(3) 0.6559(2) 0.0507(7) Uani 1 1 d . . . . .
H21A H 0.189055 0.221975 0.638442 0.076 Uiso 1 1 calc R U . . .
H21B H 0.316656 0.350085 0.720149 0.076 Uiso 1 1 calc R U . . .
H21C H 0.358394 0.208814 0.665602 0.076 Uiso 1 1 calc R U . . .
O1A O 0.5554(18) 0.2115(12) 0.0297(12) 0.036(2) Uani 0.5 1 d D U P A 1
C22A C 0.609(3) 0.3265(14) 0.0308(10) 0.059(6) Uani 0.5 1 d D U P A 1
C23A C 0.595(2) 0.3320(18) -0.0728(10) 0.070(5) Uani 0.5 1 d D U P A 1
H23A H 0.614804 0.426320 -0.064111 0.105 Uiso 0.5 1 calc R U P A 1
H23B H 0.493487 0.286825 -0.118627 0.105 Uiso 0.5 1 calc R U P A 1
H23C H 0.665889 0.286355 -0.103344 0.105 Uiso 0.5 1 calc R U P A 1
O2A O 0.6563(14) 0.4289(13) 0.1119(10) 0.073(3) Uani 0.5 1 d D U P A 1
O1S O 0.3638(15) 0.0178(13) 0.0711(8) 0.041(2) Uani 0.5 1 d . U P A 1
H1S H 0.409100 -0.064436 0.039700 0.061 Uiso 0.5 1 d . U P B 1
C1S C 0.220(3) -0.021(2) 0.0797(18) 0.052(4) Uani 0.5 1 d . U P A 1
H1S1 H 0.144200 -0.008721 0.026821 0.077 Uiso 0.5 1 calc R U P A 1
H1S2 H 0.214636 0.035082 0.148731 0.077 Uiso 0.5 1 calc R U P A 1
H1S3 H 0.200975 -0.116042 0.069480 0.077 Uiso 0.5 1 calc R U P A 1
P1A P 0.20075(14) 0.82657(13) 0.34538(14) 0.0312(15) Uani 0.5 1 d D U P C 1
F1A F 0.2060(10) 0.7199(7) 0.3980(6) 0.067(4) Uani 0.5 1 d D U P C 1
F2A F 0.1989(10) 0.9338(7) 0.2954(6) 0.082(3) Uani 0.5 1 d D U P C 1
F3A F 0.0878(8) 0.7151(6) 0.2446(5) 0.120(3) Uani 0.5 1 d D U P C 1
F4A F 0.0734(6) 0.8744(7) 0.3911(6) 0.093(2) Uani 0.5 1 d D U P C 1
F5A F 0.3324(7) 0.7799(8) 0.3027(6) 0.096(3) Uani 0.5 1 d D U P C 1
F6A F 0.3179(6) 0.9338(6) 0.4461(4) 0.081(2) Uani 0.5 1 d D U P C 1
O1B O 0.5814(18) 0.2222(11) 0.0348(12) 0.035(2) Uani 0.5 1 d D U P A 2
C22B C 0.6073(19) 0.3434(10) 0.0397(7) 0.032(3) Uani 0.5 1 d D U P A 2
C23B C 0.622(2) 0.3586(17) -0.0565(10) 0.059(3) Uani 0.5 1 d D U P A 2
H23D H 0.535671 0.387724 -0.086462 0.088 Uiso 0.5 1 calc R U P A 2
H23E H 0.628036 0.271902 -0.106819 0.088 Uiso 0.5 1 calc R U P A 2
H23F H 0.712661 0.426204 -0.039140 0.088 Uiso 0.5 1 calc R U P A 2
O2B O 0.6192(13) 0.4418(12) 0.1196(9) 0.057(2) Uani 0.5 1 d D U P A 2
O1T O 0.3827(15) 0.0137(13) 0.0943(8) 0.040(2) Uani 0.5 1 d . U P A 2
H1T H 0.409100 -0.064436 0.039700 0.061 Uiso 0.5 1 d . U P D 2
C1T C 0.236(3) -0.020(3) 0.0961(19) 0.061(5) Uani 0.5 1 d . U P A 2
H1T1 H 0.202648 0.063007 0.127709 0.092 Uiso 0.5 1 calc R U P A 2
H1T2 H 0.232138 -0.074213 0.136860 0.092 Uiso 0.5 1 calc R U P A 2
H1T3 H 0.171211 -0.071480 0.025120 0.092 Uiso 0.5 1 calc R U P A 2
P1B P 0.200300 0.826621 0.341208 0.054(2) Uani 0.5 1 d D U P E 2
F1B F 0.2209(10) 0.7347(7) 0.4065(6) 0.059(3) Uani 0.5 1 d D U P E 2
F2B F 0.1804(10) 0.9184(7) 0.2783(6) 0.075(3) Uani 0.5 1 d D U P E 2
F3B F 0.0467(6) 0.7285(8) 0.2714(5) 0.106(3) Uani 0.5 1 d D U P E 2
F4B F 0.1212(7) 0.9134(7) 0.4181(4) 0.085(2) Uani 0.5 1 d D U P E 2
F5B F 0.2796(8) 0.7391(6) 0.2669(5) 0.090(2) Uani 0.5 1 d D U P E 2
F6B F 0.3518(5) 0.9227(6) 0.4143(5) 0.087(2) Uani 0.5 1 d D U P E 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
Cu C7 1.925(2) . ?
Cu O1A 1.925(16) . ?
Cu O1B 2.002(15) . ?
Cu N1 2.086(2) . ?
Cu N2 2.112(2) . ?
Cu O1T 2.337(13) . ?
Cu O1S 2.346(13) . ?
N1 C1 1.343(3) . ?
N1 C5 1.349(3) . ?
N2 C15 1.345(3) . ?
N2 C19 1.348(3) . ?
N3 C7 1.337(3) . ?
N3 C13 1.403(3) . ?
N3 C6 1.469(3) . ?
N4 C7 1.343(3) . ?
N4 C8 1.398(3) . ?
N4 C14 1.463(3) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C13 1.390(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.418(4) . ?
C10 C20 1.512(3) . ?
C11 C12 1.388(3) . ?
C11 C21 1.510(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.504(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.386(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.366(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1A C22A 1.289(7) . ?
C22A O2A 1.232(8) . ?
C22A C23A 1.499(7) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
O1S C1S 1.43(3) . ?
O1S H1S 1.040(15) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
P1A F4A 1.561(3) . ?
P1A F6A 1.562(3) . ?
P1A F3A 1.563(4) . ?
P1A F5A 1.575(3) . ?
P1A F2A 1.583(3) . ?
P1A F1A 1.605(3) . ?
O1B C22B 1.288(7) . ?
C22B O2B 1.230(8) . ?
C22B C23B 1.497(6) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
O1T C1T 1.40(3) . ?
O1T H1T 1.033(14) . ?
C1T H1T1 0.9800 . ?
C1T H1T2 0.9800 . ?
C1T H1T3 0.9800 . ?
P1B F6B 1.558(3) . ?
P1B F5B 1.560(3) . ?
P1B F3B 1.569(4) . ?
P1B F4B 1.578(3) . ?
P1B F2B 1.579(3) . ?
P1B F1B 1.608(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
C7 Cu O1A 172.1(4) . . ?
C7 Cu O1B 169.4(3) . . ?
C7 Cu N1 88.74(9) . . ?
O1A Cu N1 96.8(5) . . ?
O1B Cu N1 92.2(5) . . ?
C7 Cu N2 87.53(9) . . ?
O1A Cu N2 87.2(5) . . ?
O1B Cu N2 91.9(5) . . ?
N1 Cu N2 175.65(8) . . ?
C7 Cu O1T 93.5(3) . . ?
O1B Cu O1T 97.1(4) . . ?
N1 Cu O1T 87.2(3) . . ?
N2 Cu O1T 90.8(3) . . ?
C7 Cu O1S 98.8(3) . . ?
O1A Cu O1S 86.4(5) . . ?
N1 Cu O1S 94.4(3) . . ?
N2 Cu O1S 84.0(3) . . ?
C1 N1 C5 118.2(2) . . ?
C1 N1 Cu 118.51(17) . . ?
C5 N1 Cu 122.97(16) . . ?
C15 N2 C19 118.6(2) . . ?
C15 N2 Cu 124.77(16) . . ?
C19 N2 Cu 116.53(18) . . ?
C7 N3 C13 110.33(18) . . ?
C7 N3 C6 122.62(19) . . ?
C13 N3 C6 126.68(19) . . ?
C7 N4 C8 110.79(18) . . ?
C7 N4 C14 122.12(19) . . ?
C8 N4 C14 127.08(19) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 121.2(2) . . ?
N1 C5 C6 119.7(2) . . ?
C4 C5 C6 119.1(2) . . ?
N3 C6 C5 113.6(2) . . ?
N3 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N3 C7 N4 107.10(19) . . ?
N3 C7 Cu 125.77(17) . . ?
N4 C7 Cu 126.64(17) . . ?
C13 C8 C9 121.2(2) . . ?
C13 C8 N4 105.58(19) . . ?
C9 C8 N4 133.3(2) . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 C20 119.4(2) . . ?
C11 C10 C20 120.1(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 C21 118.8(2) . . ?
C10 C11 C21 120.4(2) . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 N3 132.4(2) . . ?
C8 C13 N3 106.17(19) . . ?
N4 C14 C15 112.33(19) . . ?
N4 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N4 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C16 121.6(2) . . ?
N2 C15 C14 118.1(2) . . ?
C16 C15 C14 120.2(2) . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N2 C19 C18 122.3(3) . . ?
N2 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22A O1A Cu 109.6(9) . . ?
O2A C22A O1A 121.8(6) . . ?
O2A C22A C23A 121.6(7) . . ?
O1A C22A C23A 116.3(8) . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C1S O1S Cu 123.7(12) . . ?
C1S O1S H1S 112.7(14) . . ?
Cu O1S H1S 121.7(10) . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
F4A P1A F6A 89.8(3) . . ?
F4A P1A F3A 92.1(4) . . ?
F6A P1A F3A 177.6(3) . . ?
F4A P1A F5A 178.3(4) . . ?
F6A P1A F5A 88.7(4) . . ?
F3A P1A F5A 89.5(4) . . ?
F4A P1A F2A 90.5(3) . . ?
F6A P1A F2A 89.5(3) . . ?
F3A P1A F2A 92.0(3) . . ?
F5A P1A F2A 90.2(3) . . ?
F4A P1A F1A 89.8(3) . . ?
F6A P1A F1A 89.3(3) . . ?
F3A P1A F1A 89.2(3) . . ?
F5A P1A F1A 89.4(3) . . ?
F2A P1A F1A 178.7(4) . . ?
C22B O1B Cu 104.7(9) . . ?
O2B C22B O1B 121.6(5) . . ?
O2B C22B C23B 121.7(6) . . ?
O1B C22B C23B 116.8(7) . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C1T O1T Cu 121.4(14) . . ?
C1T O1T H1T 111.8(14) . . ?
Cu O1T H1T 122.8(10) . . ?
O1T C1T H1T1 109.5 . . ?
O1T C1T H1T2 109.5 . . ?
H1T1 C1T H1T2 109.5 . . ?
O1T C1T H1T3 109.5 . . ?
H1T1 C1T H1T3 109.5 . . ?
H1T2 C1T H1T3 109.5 . . ?
F6B P1B F5B 91.0(4) . . ?
F6B P1B F3B 177.7(3) . . ?
F5B P1B F3B 90.2(4) . . ?
F6B P1B F4B 88.8(3) . . ?
F5B P1B F4B 178.6(3) . . ?
F3B P1B F4B 90.0(4) . . ?
F6B P1B F2B 90.5(3) . . ?
F5B P1B F2B 91.0(3) . . ?
F3B P1B F2B 91.5(3) . . ?
F4B P1B F2B 90.4(3) . . ?
F6B P1B F1B 89.1(3) . . ?
F5B P1B F1B 89.6(3) . . ?
F3B P1B F1B 88.9(3) . . ?
F4B P1B F1B 89.1(3) . . ?
F2B P1B F1B 179.3(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
C5 N1 C1 C2 1.0(4) . . . . ?
Cu N1 C1 C2 174.4(2) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C1 N1 C5 C4 -0.8(4) . . . . ?
Cu N1 C5 C4 -173.92(19) . . . . ?
C1 N1 C5 C6 -178.3(2) . . . . ?
Cu N1 C5 C6 8.6(3) . . . . ?
C3 C4 C5 N1 0.1(4) . . . . ?
C3 C4 C5 C6 177.6(2) . . . . ?
C7 N3 C6 C5 45.2(3) . . . . ?
C13 N3 C6 C5 -142.4(2) . . . . ?
N1 C5 C6 N3 -49.5(3) . . . . ?
C4 C5 C6 N3 133.0(2) . . . . ?
C13 N3 C7 N4 1.6(3) . . . . ?
C6 N3 C7 N4 175.1(2) . . . . ?
C13 N3 C7 Cu -170.83(16) . . . . ?
C6 N3 C7 Cu 2.7(3) . . . . ?
C8 N4 C7 N3 -1.2(3) . . . . ?
C14 N4 C7 N3 179.4(2) . . . . ?
C8 N4 C7 Cu 171.12(16) . . . . ?
C14 N4 C7 Cu -8.3(3) . . . . ?
C7 N4 C8 C13 0.4(3) . . . . ?
C14 N4 C8 C13 179.7(2) . . . . ?
C7 N4 C8 C9 -178.5(2) . . . . ?
C14 N4 C8 C9 0.9(4) . . . . ?
C13 C8 C9 C10 -2.4(3) . . . . ?
N4 C8 C9 C10 176.3(2) . . . . ?
C8 C9 C10 C11 1.9(3) . . . . ?
C8 C9 C10 C20 -176.6(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C20 C10 C11 C12 178.5(2) . . . . ?
C9 C10 C11 C21 -179.1(2) . . . . ?
C20 C10 C11 C21 -0.6(4) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C21 C11 C12 C13 177.8(2) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
C11 C12 C13 N3 -177.3(2) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
N4 C8 C13 C12 -177.9(2) . . . . ?
C9 C8 C13 N3 179.6(2) . . . . ?
N4 C8 C13 N3 0.6(2) . . . . ?
C7 N3 C13 C12 176.9(2) . . . . ?
C6 N3 C13 C12 3.7(4) . . . . ?
C7 N3 C13 C8 -1.4(3) . . . . ?
C6 N3 C13 C8 -174.5(2) . . . . ?
C7 N4 C14 C15 54.0(3) . . . . ?
C8 N4 C14 C15 -125.3(2) . . . . ?
C19 N2 C15 C16 0.0(4) . . . . ?
Cu N2 C15 C16 -175.86(19) . . . . ?
C19 N2 C15 C14 -176.9(2) . . . . ?
Cu N2 C15 C14 7.3(3) . . . . ?
N4 C14 C15 N2 -50.8(3) . . . . ?
N4 C14 C15 C16 132.3(2) . . . . ?
N2 C15 C16 C17 -1.2(4) . . . . ?
C14 C15 C16 C17 175.6(3) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C15 N2 C19 C18 1.4(4) . . . . ?
Cu N2 C19 C18 177.6(2) . . . . ?
C17 C18 C19 N2 -1.5(5) . . . . ?
Cu O1A C22A O2A 17(3) . . . . ?
Cu O1A C22A C23A -156.7(16) . . . . ?
Cu O1B C22B O2B 16(2) . . . . ?
Cu O1B C22B C23B -163.6(14) . . . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.057



