# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2430824'
loop_
_audit_author_name
_audit_author_address
'Fedor Dolgushin'
;Kurnakov Institute of general and inorganic chemistry of Russian Academy of Sciences (IGIC RAS)
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 F12 N8 Zn'
_chemical_formula_weight         663.79

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   8.7719(14)
_cell_length_b                   11.2287(18)
_cell_length_c                   15.981(3)
_cell_angle_alpha                70.082(3)
_cell_angle_beta                 89.231(3)
_cell_angle_gamma                72.118(3)
_cell_volume                     1401.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3421
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.81

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.982
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12505
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.362
_diffrn_reflns_theta_max         25.999
_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             5499
_reflns_number_gt                3679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0969P)²+0.4267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     422
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.63319(6) 0.63720(4) 0.73263(3) 0.0767(2) Uani 1 1 d . . . . .
N1 N 0.4311(4) 0.7752(3) 0.7395(2) 0.0780(8) Uani 1 1 d . . . . .
N2 N 0.4391(4) 0.8461(3) 0.7919(2) 0.0824(9) Uani 1 1 d . . . . .
N3 N 0.6285(4) 0.4506(3) 0.7626(2) 0.0779(8) Uani 1 1 d . . . . .
N4 N 0.6673(4) 0.3939(3) 0.6996(2) 0.0819(9) Uani 1 1 d . . . . .
N5 N 0.7981(4) 0.6430(3) 0.8151(2) 0.0781(8) Uani 1 1 d . . . . .
N6 N 0.7646(5) 0.7351(4) 0.8551(2) 0.0815(9) Uani 1 1 d . . . . .
H6 H 0.664(6) 0.788(5) 0.855(3) 0.104(16) Uiso 1 1 d . . . . .
N7 N 0.7003(4) 0.6857(3) 0.6086(2) 0.0774(8) Uani 1 1 d . . . . .
N8 N 0.7262(4) 0.6031(4) 0.5611(2) 0.0805(9) Uani 1 1 d . . . . .
H8 H 0.727(4) 0.532(4) 0.588(2) 0.051(10) Uiso 1 1 d . . . . .
C1 C 0.2912(6) 0.9261(4) 0.7885(3) 0.0880(12) Uani 1 1 d . . . . .
C2 C 0.2629(6) 1.0158(5) 0.8394(4) 0.1203(19) Uani 1 1 d D . . . .
C3 C 0.1856(6) 0.9091(5) 0.7348(4) 0.1029(14) Uani 1 1 d . . . . .
H3A H 0.075231 0.952844 0.721933 0.123 Uiso 1 1 calc R U . . .
C4 C 0.2791(5) 0.8134(4) 0.7045(3) 0.0843(11) Uani 1 1 d . . . . .
C5 C 0.2309(6) 0.7572(5) 0.6437(3) 0.1116(16) Uani 1 1 d D . . . .
C6 C 0.5967(5) 0.3611(4) 0.8356(3) 0.0759(10) Uani 1 1 d . . . . .
C7 C 0.5535(5) 0.3926(4) 0.9159(3) 0.0916(12) Uani 1 1 d D . . . .
C8 C 0.6154(6) 0.2450(4) 0.8205(3) 0.0928(12) Uani 1 1 d . . . . .
H8A H 0.602913 0.166138 0.859431 0.111 Uiso 1 1 calc R U . . .
C9 C 0.6568(5) 0.2716(4) 0.7346(3) 0.0849(11) Uani 1 1 d . . . . .
C10 C 0.6941(6) 0.1827(4) 0.6837(3) 0.1110(17) Uani 1 1 d D . . . .
C11 C 0.8937(6) 0.7249(5) 0.9025(3) 0.0915(12) Uani 1 1 d . . . . .
C12 C 0.8852(8) 0.8178(6) 0.9529(4) 0.130(2) Uani 1 1 d . . . . .
H12A H 0.793102 0.822647 0.986261 0.195 Uiso 1 1 calc R U . . .
H12B H 0.875869 0.905383 0.911309 0.195 Uiso 1 1 calc R U . . .
H12C H 0.981213 0.784697 0.993182 0.195 Uiso 1 1 calc R U . . .
C13 C 1.0166(6) 0.6234(5) 0.8928(3) 0.1034(14) Uani 1 1 d . . . . .
H13A H 1.122322 0.593064 0.918367 0.124 Uiso 1 1 calc R U . . .
C14 C 0.9545(6) 0.5735(4) 0.8373(3) 0.0860(11) Uani 1 1 d . . . . .
C15 C 1.0318(7) 0.4625(6) 0.8055(4) 0.1233(18) Uani 1 1 d . . . . .
H15A H 0.987413 0.391467 0.831328 0.185 Uiso 1 1 calc R U . . .
H15B H 1.145625 0.430122 0.822862 0.185 Uiso 1 1 calc R U . . .
H15C H 1.012771 0.493824 0.741437 0.185 Uiso 1 1 calc R U . . .
C16 C 0.7248(5) 0.7958(4) 0.5547(3) 0.0852(11) Uani 1 1 d . . . . .
C17 C 0.7026(7) 0.9127(5) 0.5844(4) 0.1119(16) Uani 1 1 d . . . . .
H17A H 0.715451 0.882090 0.648569 0.168 Uiso 1 1 calc R U . . .
H17B H 0.596709 0.975669 0.562650 0.168 Uiso 1 1 calc R U . . .
H17C H 0.781574 0.955257 0.560992 0.168 Uiso 1 1 calc R U . . .
C18 C 0.7659(6) 0.7823(5) 0.4739(3) 0.1023(14) Uani 1 1 d . . . . .
H18A H 0.789245 0.845410 0.424884 0.123 Uiso 1 1 calc R U . . .
C19 C 0.7656(6) 0.6584(5) 0.4801(3) 0.0903(12) Uani 1 1 d . . . . .
C20 C 0.7997(8) 0.5854(6) 0.4153(4) 0.130(2) Uani 1 1 d . . . . .
H20A H 0.861862 0.624339 0.370695 0.195 Uiso 1 1 calc R U . . .
H20B H 0.699891 0.592220 0.387073 0.195 Uiso 1 1 calc R U . . .
H20C H 0.858982 0.492916 0.446837 0.195 Uiso 1 1 calc R U . . .
F1 F 0.2307(18) 1.1418(5) 0.7909(5) 0.211(5) Uani 0.686(5) 1 d D . P A 1
F2 F 0.1457(14) 1.0121(13) 0.8898(9) 0.216(5) Uani 0.686(5) 1 d D . P A 1
F3 F 0.3874(8) 0.9992(8) 0.8938(6) 0.155(2) Uani 0.686(5) 1 d D . P A 1
F1' F 0.263(5) 0.9607(13) 0.9265(6) 0.211(5) Uani 0.314(5) 1 d D . P A 2
F2' F 0.341(3) 1.103(2) 0.814(2) 0.216(5) Uani 0.314(5) 1 d D . P A 2
F3' F 0.1131(13) 1.0972(17) 0.8125(14) 0.155(2) Uani 0.314(5) 1 d D . P A 2
F4 F 0.1181(13) 0.8432(9) 0.5793(8) 0.167(3) Uani 0.533(4) 1 d D . P B 1
F5 F 0.204(3) 0.6442(14) 0.6869(7) 0.250(7) Uani 0.533(4) 1 d D . P B 1
F6 F 0.3394(8) 0.7123(13) 0.5943(6) 0.1303(19) Uani 0.533(4) 1 d D . P B 1
F4' F 0.3124(15) 0.6291(8) 0.6630(12) 0.167(3) Uani 0.467(4) 1 d D . P B 2
F5' F 0.276(3) 0.809(2) 0.5646(7) 0.250(7) Uani 0.467(4) 1 d D . P B 2
F6' F 0.0839(8) 0.7518(14) 0.6495(8) 0.1303(19) Uani 0.467(4) 1 d D . P B 2
F7 F 0.6784(6) 0.3582(10) 0.9730(4) 0.158(2) Uani 0.786(5) 1 d D . P C 1
F8 F 0.4530(8) 0.3356(7) 0.9601(3) 0.1403(18) Uani 0.786(5) 1 d D . P C 1
F9 F 0.4846(11) 0.5209(4) 0.9006(3) 0.147(2) Uani 0.786(5) 1 d D . P C 1
F7' F 0.4003(13) 0.464(3) 0.9057(16) 0.158(2) Uani 0.214(5) 1 d D . P C 2
F8' F 0.621(4) 0.475(3) 0.9301(15) 0.1403(18) Uani 0.214(5) 1 d D . P C 2
F9' F 0.606(4) 0.2899(12) 0.9907(6) 0.147(2) Uani 0.214(5) 1 d D . P C 2
F10 F 0.8124(12) 0.1967(8) 0.6332(7) 0.206(5) Uani 0.675(7) 1 d D . P D 1
F11 F 0.5739(10) 0.1942(13) 0.6323(10) 0.226(5) Uani 0.675(7) 1 d D . P D 1
F12 F 0.7619(10) 0.0547(4) 0.7305(4) 0.140(2) Uani 0.675(7) 1 d D . P D 1
F10' F 0.619(3) 0.093(2) 0.7169(16) 0.206(5) Uani 0.325(7) 1 d D . P D 2
F11' F 0.8372(11) 0.145(3) 0.6567(16) 0.226(5) Uani 0.325(7) 1 d D . P D 2
F12' F 0.632(2) 0.2429(12) 0.6002(5) 0.140(2) Uani 0.325(7) 1 d D . P D 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
Zn1 N1 1.995(3) . ?
Zn1 N3 1.998(3) . ?
Zn1 N7 2.000(3) . ?
Zn1 N5 2.001(3) . ?
N1 C4 1.334(5) . ?
N1 N2 1.353(4) . ?
N2 C1 1.321(5) . ?
N3 C6 1.346(5) . ?
N3 N4 1.353(4) . ?
N4 C9 1.326(5) . ?
N5 C14 1.336(6) . ?
N5 N6 1.350(4) . ?
N6 C11 1.324(6) . ?
N6 H6 0.90(5) . ?
N7 C16 1.323(5) . ?
N7 N8 1.355(4) . ?
N8 C19 1.324(6) . ?
N8 H8 0.77(3) . ?
C1 C3 1.368(7) . ?
C1 C2 1.462(6) . ?
C2 F2 1.299(4) . ?
C2 F1 1.302(4) . ?
C2 F2' 1.313(5) . ?
C2 F1' 1.316(5) . ?
C2 F3' 1.325(5) . ?
C2 F3 1.332(4) . ?
C3 C4 1.367(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.454(7) . ?
C5 F6' 1.309(5) . ?
C5 F5' 1.311(5) . ?
C5 F5 1.314(5) . ?
C5 F4 1.317(5) . ?
C5 F6 1.319(5) . ?
C5 F4' 1.321(5) . ?
C6 C8 1.367(5) . ?
C6 C7 1.459(6) . ?
C7 F8 1.307(4) . ?
C7 F7 1.308(4) . ?
C7 F9' 1.312(5) . ?
C7 F7' 1.314(5) . ?
C7 F9 1.315(4) . ?
C7 F8' 1.318(5) . ?
C8 C9 1.371(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.453(6) . ?
C10 F11 1.292(4) . ?
C10 F12' 1.309(5) . ?
C10 F11' 1.313(5) . ?
C10 F12 1.317(4) . ?
C10 F10 1.320(5) . ?
C10 F10' 1.326(5) . ?
C11 C13 1.359(7) . ?
C11 C12 1.505(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.391(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.475(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.381(6) . ?
C16 C17 1.501(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.361(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.501(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N1 Zn1 N3 117.46(13) . . ?
N1 Zn1 N7 110.73(13) . . ?
N3 Zn1 N7 104.37(12) . . ?
N1 Zn1 N5 104.46(13) . . ?
N3 Zn1 N5 110.79(13) . . ?
N7 Zn1 N5 108.93(14) . . ?
C4 N1 N2 108.8(3) . . ?
C4 N1 Zn1 133.5(3) . . ?
N2 N1 Zn1 117.7(3) . . ?
C1 N2 N1 106.5(4) . . ?
C6 N3 N4 108.6(3) . . ?
C6 N3 Zn1 134.0(2) . . ?
N4 N3 Zn1 117.4(3) . . ?
C9 N4 N3 106.4(3) . . ?
C14 N5 N6 106.5(4) . . ?
C14 N5 Zn1 131.5(3) . . ?
N6 N5 Zn1 121.8(3) . . ?
C11 N6 N5 111.3(4) . . ?
C11 N6 H6 125(3) . . ?
N5 N6 H6 123(3) . . ?
C16 N7 N8 105.2(3) . . ?
C16 N7 Zn1 131.7(3) . . ?
N8 N7 Zn1 123.1(3) . . ?
C19 N8 N7 112.0(4) . . ?
C19 N8 H8 133(3) . . ?
N7 N8 H8 115(3) . . ?
N2 C1 C3 111.2(4) . . ?
N2 C1 C2 118.7(4) . . ?
C3 C1 C2 130.0(4) . . ?
F2 C2 F1 104.7(7) . . ?
F2' C2 F1' 114.9(17) . . ?
F2' C2 F3' 100.1(15) . . ?
F1' C2 F3' 103.8(15) . . ?
F2 C2 F3 104.5(7) . . ?
F1 C2 F3 100.0(7) . . ?
F2 C2 C1 115.0(5) . . ?
F1 C2 C1 114.7(5) . . ?
F2' C2 C1 113.7(8) . . ?
F1' C2 C1 116.5(7) . . ?
F3' C2 C1 105.4(7) . . ?
F3 C2 C1 116.1(4) . . ?
C4 C3 C1 104.3(4) . . ?
C4 C3 H3A 127.9 . . ?
C1 C3 H3A 127.9 . . ?
N1 C4 C3 109.2(4) . . ?
N1 C4 C5 122.4(4) . . ?
C3 C4 C5 128.4(5) . . ?
F6' C5 F5' 119.1(11) . . ?
F5 C5 F4 114.6(10) . . ?
F5 C5 F6 97.7(8) . . ?
F4 C5 F6 98.9(7) . . ?
F6' C5 F4' 100.2(7) . . ?
F5' C5 F4' 100.8(11) . . ?
F6' C5 C4 113.8(5) . . ?
F5' C5 C4 108.9(6) . . ?
F5 C5 C4 111.9(6) . . ?
F4 C5 C4 114.5(5) . . ?
F6 C5 C4 117.7(5) . . ?
F4' C5 C4 113.0(6) . . ?
N3 C6 C8 109.4(4) . . ?
N3 C6 C7 121.5(3) . . ?
C8 C6 C7 129.1(4) . . ?
F8 C7 F7 106.3(5) . . ?
F9' C7 F7' 116.8(17) . . ?
F8 C7 F9 104.7(5) . . ?
F7 C7 F9 104.0(5) . . ?
F9' C7 F8' 100.0(16) . . ?
F7' C7 F8' 101.2(16) . . ?
F8 C7 C6 114.1(4) . . ?
F7 C7 C6 112.8(4) . . ?
F9' C7 C6 114.0(7) . . ?
F7' C7 C6 109.8(8) . . ?
F9 C7 C6 114.0(4) . . ?
F8' C7 C6 114.1(8) . . ?
C6 C8 C9 103.9(4) . . ?
C6 C8 H8A 128.0 . . ?
C9 C8 H8A 128.0 . . ?
N4 C9 C8 111.6(3) . . ?
N4 C9 C10 120.2(4) . . ?
C8 C9 C10 128.1(4) . . ?
F12' C10 F11' 89.8(12) . . ?
F11 C10 F12 107.8(7) . . ?
F11 C10 F10 107.1(9) . . ?
F12 C10 F10 96.7(6) . . ?
F12' C10 F10' 103.6(14) . . ?
F11' C10 F10' 119.0(13) . . ?
F11 C10 C9 114.6(5) . . ?
F12' C10 C9 112.7(6) . . ?
F11' C10 C9 121.8(8) . . ?
F12 C10 C9 115.8(4) . . ?
F10 C10 C9 113.1(5) . . ?
F10' C10 C9 107.1(7) . . ?
N6 C11 C13 106.8(4) . . ?
N6 C11 C12 120.8(5) . . ?
C13 C11 C12 132.4(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 107.1(4) . . ?
C11 C13 H13A 126.4 . . ?
C14 C13 H13A 126.4 . . ?
N5 C14 C13 108.2(4) . . ?
N5 C14 C15 121.0(4) . . ?
C13 C14 C15 130.8(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C16 C18 109.9(4) . . ?
N7 C16 C17 120.3(4) . . ?
C18 C16 C17 129.7(5) . . ?
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 . . ?
C19 C18 C16 106.6(4) . . ?
C19 C18 H18A 126.7 . . ?
C16 C18 H18A 126.7 . . ?
N8 C19 C18 106.3(4) . . ?
N8 C19 C20 121.4(5) . . ?
C18 C19 C20 132.3(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C4 N1 N2 C1 0.4(4) . . . . ?
Zn1 N1 N2 C1 -177.5(3) . . . . ?
C6 N3 N4 C9 0.7(5) . . . . ?
Zn1 N3 N4 C9 179.6(3) . . . . ?
C14 N5 N6 C11 -0.8(5) . . . . ?
Zn1 N5 N6 C11 -176.4(3) . . . . ?
C16 N7 N8 C19 0.0(5) . . . . ?
Zn1 N7 N8 C19 178.4(3) . . . . ?
N1 N2 C1 C3 0.1(5) . . . . ?
N1 N2 C1 C2 -179.9(4) . . . . ?
N2 C1 C2 F2 -129.6(10) . . . . ?
C3 C1 C2 F2 50.3(11) . . . . ?
N2 C1 C2 F1 108.8(9) . . . . ?
C3 C1 C2 F1 -71.2(10) . . . . ?
N2 C1 C2 F2' 62(2) . . . . ?
C3 C1 C2 F2' -118.3(19) . . . . ?
N2 C1 C2 F1' -75(2) . . . . ?
C3 C1 C2 F1' 105(2) . . . . ?
N2 C1 C2 F3' 170.3(12) . . . . ?
C3 C1 C2 F3' -9.8(13) . . . . ?
N2 C1 C2 F3 -7.2(8) . . . . ?
C3 C1 C2 F3 172.8(7) . . . . ?
N2 C1 C3 C4 -0.5(5) . . . . ?
C2 C1 C3 C4 179.5(5) . . . . ?
N2 N1 C4 C3 -0.7(5) . . . . ?
Zn1 N1 C4 C3 176.7(3) . . . . ?
N2 N1 C4 C5 179.0(4) . . . . ?
Zn1 N1 C4 C5 -3.5(7) . . . . ?
C1 C3 C4 N1 0.7(5) . . . . ?
C1 C3 C4 C5 -179.0(5) . . . . ?
N1 C4 C5 F6' 148.5(8) . . . . ?
C3 C4 C5 F6' -31.8(10) . . . . ?
N1 C4 C5 F5' -76.1(15) . . . . ?
C3 C4 C5 F5' 103.6(15) . . . . ?
N1 C4 C5 F5 84.0(14) . . . . ?
C3 C4 C5 F5 -96.3(13) . . . . ?
N1 C4 C5 F4 -143.4(9) . . . . ?
C3 C4 C5 F4 36.3(10) . . . . ?
N1 C4 C5 F6 -27.9(9) . . . . ?
C3 C4 C5 F6 151.8(8) . . . . ?
N1 C4 C5 F4' 35.1(12) . . . . ?
C3 C4 C5 F4' -145.2(11) . . . . ?
N4 N3 C6 C8 0.2(5) . . . . ?
Zn1 N3 C6 C8 -178.4(3) . . . . ?
N4 N3 C6 C7 179.0(4) . . . . ?
Zn1 N3 C6 C7 0.3(6) . . . . ?
N3 C6 C7 F8 147.2(5) . . . . ?
C8 C6 C7 F8 -34.3(7) . . . . ?
N3 C6 C7 F7 -91.4(7) . . . . ?
C8 C6 C7 F7 87.0(7) . . . . ?
N3 C6 C7 F9' -146.1(18) . . . . ?
C8 C6 C7 F9' 32.3(19) . . . . ?
N3 C6 C7 F7' 80.7(18) . . . . ?
C8 C6 C7 F7' -100.8(19) . . . . ?
N3 C6 C7 F9 27.0(7) . . . . ?
C8 C6 C7 F9 -154.6(6) . . . . ?
N3 C6 C7 F8' -32.0(18) . . . . ?
C8 C6 C7 F8' 146.4(18) . . . . ?
N3 C6 C8 C9 -1.1(5) . . . . ?
C7 C6 C8 C9 -179.7(4) . . . . ?
N3 N4 C9 C8 -1.4(5) . . . . ?
N3 N4 C9 C10 -179.0(4) . . . . ?
C6 C8 C9 N4 1.6(5) . . . . ?
C6 C8 C9 C10 178.8(5) . . . . ?
N4 C9 C10 F11 -87.7(11) . . . . ?
C8 C9 C10 F11 95.3(11) . . . . ?
N4 C9 C10 F12' -43.9(12) . . . . ?
C8 C9 C10 F12' 139.1(11) . . . . ?
N4 C9 C10 F11' 60.9(16) . . . . ?
C8 C9 C10 F11' -116.2(16) . . . . ?
N4 C9 C10 F12 145.8(6) . . . . ?
C8 C9 C10 F12 -31.3(9) . . . . ?
N4 C9 C10 F10 35.5(8) . . . . ?
C8 C9 C10 F10 -141.6(7) . . . . ?
N4 C9 C10 F10' -157.2(16) . . . . ?
C8 C9 C10 F10' 25.8(17) . . . . ?
N5 N6 C11 C13 0.5(5) . . . . ?
N5 N6 C11 C12 179.8(4) . . . . ?
N6 C11 C13 C14 0.0(5) . . . . ?
C12 C11 C13 C14 -179.2(5) . . . . ?
N6 N5 C14 C13 0.7(5) . . . . ?
Zn1 N5 C14 C13 175.8(3) . . . . ?
N6 N5 C14 C15 179.3(4) . . . . ?
Zn1 N5 C14 C15 -5.6(7) . . . . ?
C11 C13 C14 N5 -0.4(6) . . . . ?
C11 C13 C14 C15 -178.8(5) . . . . ?
N8 N7 C16 C18 -0.1(5) . . . . ?
Zn1 N7 C16 C18 -178.3(3) . . . . ?
N8 N7 C16 C17 178.5(4) . . . . ?
Zn1 N7 C16 C17 0.3(7) . . . . ?
N7 C16 C18 C19 0.1(6) . . . . ?
C17 C16 C18 C19 -178.2(5) . . . . ?
N7 N8 C19 C18 0.1(5) . . . . ?
N7 N8 C19 C20 -179.9(4) . . . . ?
C16 C18 C19 N8 -0.1(5) . . . . ?
C16 C18 C19 C20 179.9(6) . . . . ?

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
_geom_hbond_publ_flag
N6 H6 N2 0.90(6) 2.04(5) 2.786(6) 140(5) . yes
N8 H8 N4 0.77(4) 2.11(3) 2.803(5) 151(4) . yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_Cu1_tw
_database_code_depnum_ccdc_archive 'CCDC 2430826'
loop_
_audit_author_name
_audit_author_address
'Fedor Dolgushin'
;Kurnakov Institute of general and inorganic chemistry of Russian Academy of Sciences (IGIC RAS)
Russia
;
_audit_update_record             
;
2025-03-12 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Cu F12 N8'
_chemical_formula_weight         661.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

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

_cell_length_a                   17.982(3)
_cell_length_b                   17.969(3)
_cell_length_c                   15.915(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5142.2(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7832
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.47

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             2648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.964
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6763
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6763
_reflns_number_gt                6060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
Refined as a 2-component twin. Twin law is 0 1 0 1 0 0 0 0 -1, HKLF 5 refinement 
with BASF = 0.191(2). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2634 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.001(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6763
_refine_ls_number_parameters     383
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.58128(2) 0.08009(2) 0.39701(4) 0.01582(11) Uani 1 1 d . . . . .
F1 F 0.83980(15) 0.0521(2) 0.4336(2) 0.0517(9) Uani 1 1 d . . . . .
F2 F 0.76295(17) 0.0374(2) 0.53573(19) 0.0454(8) Uani 1 1 d . . . . .
F3 F 0.73965(16) 0.11823(16) 0.4398(2) 0.0418(7) Uani 1 1 d . . . . .
F4 F 0.7342(3) -0.1698(3) 0.2075(3) 0.0926(19) Uani 1 1 d . . . . .
F5 F 0.7276(2) -0.2301(2) 0.3239(3) 0.0757(15) Uani 1 1 d . . . . .
F6 F 0.62921(14) -0.19672(15) 0.25940(19) 0.0332(6) Uani 1 1 d . . . . .
F7 F 0.61923(16) 0.23632(17) 0.3470(2) 0.0388(7) Uani 1 1 d . . . . .
F8 F 0.53207(19) 0.26083(17) 0.25906(18) 0.0407(7) Uani 1 1 d . . . . .
F9 F 0.5555(2) 0.33771(16) 0.3585(2) 0.0475(8) Uani 1 1 d . . . . .
F10 F 0.2920(2) 0.2529(2) 0.5161(3) 0.0831(16) Uani 1 1 d . . . . .
F11 F 0.3626(2) 0.2238(2) 0.6195(2) 0.0531(9) Uani 1 1 d . . . . .
F12 F 0.30825(15) 0.13804(16) 0.54771(18) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.6566(2) 0.00096(18) 0.3760(2) 0.0196(8) Uani 1 1 d . . . . .
N2 N 0.63829(18) -0.0591(2) 0.3291(2) 0.0216(7) Uani 1 1 d . . . . .
N3 N 0.50285(17) 0.1553(2) 0.4197(2) 0.0181(7) Uani 1 1 d . . . . .
N4 N 0.44683(19) 0.13933(19) 0.4736(2) 0.0206(7) Uani 1 1 d . . . . .
N5 N 0.5936(2) 0.0676(2) 0.5201(2) 0.0206(7) Uani 1 1 d . . . . .
N6 N 0.5896(2) -0.0003(2) 0.5583(3) 0.0204(7) Uani 1 1 d . . . . .
H6 H 0.580(3) -0.039(4) 0.527(4) 0.034(16) Uiso 1 1 d . . . . .
N7 N 0.5655(2) 0.08938(19) 0.2741(2) 0.0184(7) Uani 1 1 d . . . . .
N8 N 0.49574(18) 0.0871(2) 0.2392(2) 0.0202(7) Uani 1 1 d . . . . .
H8 H 0.454(3) 0.089(3) 0.274(3) 0.021(12) Uiso 1 1 d . . . . .
C1 C 0.7280(2) -0.0075(2) 0.4023(3) 0.0221(8) Uani 1 1 d . . . . .
C2 C 0.7669(2) 0.0503(3) 0.4533(3) 0.0322(10) Uani 1 1 d . . . . .
C3 C 0.7570(2) -0.0730(3) 0.3718(3) 0.0257(9) Uani 1 1 d . . . . .
H3 H 0.805642 -0.092499 0.379465 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6984(2) -0.1035(2) 0.3272(3) 0.0233(8) Uani 1 1 d . . . . .
C5 C 0.6974(2) -0.1743(3) 0.2796(4) 0.0372(11) Uani 1 1 d . . . . .
C6 C 0.49671(19) 0.2275(2) 0.3973(3) 0.0216(8) Uani 1 1 d . . . . .
C7 C 0.5506(3) 0.2645(3) 0.3399(3) 0.0301(9) Uani 1 1 d . . . . .
C8 C 0.4360(3) 0.2598(2) 0.4346(3) 0.0276(9) Uani 1 1 d . . . . .
H8A H 0.418240 0.309439 0.429577 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4070(2) 0.2013(2) 0.4818(3) 0.0244(8) Uani 1 1 d . . . . .
C10 C 0.3421(3) 0.2042(3) 0.5410(3) 0.0329(10) Uani 1 1 d . . . . .
C11 C 0.6040(2) 0.1167(3) 0.5825(3) 0.0226(9) Uani 1 1 d . . . . .
C12 C 0.6120(3) 0.1981(3) 0.5672(3) 0.0324(10) Uani 1 1 d . . . . .
H12A H 0.634940 0.206249 0.512158 0.049 Uiso 1 1 calc R U . . .
H12B H 0.643369 0.220001 0.611051 0.049 Uiso 1 1 calc R U . . .
H12C H 0.562785 0.221605 0.568411 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6066(3) 0.0794(3) 0.6601(3) 0.0265(9) Uani 1 1 d . . . . .
H13 H 0.613700 0.100953 0.713966 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5968(3) 0.0058(3) 0.6420(3) 0.0243(9) Uani 1 1 d . . . . .
C15 C 0.5936(3) -0.0604(3) 0.6986(3) 0.0336(10) Uani 1 1 d . . . . .
H15A H 0.558446 -0.096879 0.675689 0.050 Uiso 1 1 calc R U . . .
H15B H 0.577119 -0.044895 0.754567 0.050 Uiso 1 1 calc R U . . .
H15C H 0.643081 -0.082998 0.702546 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6130(2) 0.1000(3) 0.2096(3) 0.0228(8) Uani 1 1 d . . . . .
C17 C 0.6945(2) 0.1066(3) 0.2215(3) 0.0301(9) Uani 1 1 d . . . . .
H17A H 0.704788 0.131293 0.275168 0.045 Uiso 1 1 calc R U . . .
H17B H 0.715808 0.135893 0.175521 0.045 Uiso 1 1 calc R U . . .
H17C H 0.716878 0.056810 0.221755 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5731(3) 0.1028(3) 0.1345(3) 0.0260(9) Uani 1 1 d . . . . .
H18 H 0.593000 0.109385 0.079688 0.031 Uiso 1 1 calc R U . . .
C19 C 0.4989(2) 0.0942(3) 0.1556(3) 0.0238(9) Uani 1 1 d . . . . .
C20 C 0.4308(3) 0.0925(3) 0.1016(3) 0.0322(11) Uani 1 1 d . . . . .
H20A H 0.386548 0.088471 0.137203 0.048 Uiso 1 1 calc R U . . .
H20B H 0.433210 0.049579 0.063693 0.048 Uiso 1 1 calc R U . . .
H20C H 0.428062 0.138395 0.068397 0.048 Uiso 1 1 calc R U . . .


_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 N7 1.983(4) . ?
Cu1 N5 1.985(4) . ?
Cu1 N3 1.987(3) . ?
Cu1 N1 1.992(3) . ?
F1 C2 1.348(5) . ?
F2 C2 1.335(6) . ?
F3 C2 1.332(6) . ?
F4 C5 1.327(7) . ?
F5 C5 1.341(7) . ?
F6 C5 1.330(5) . ?
F7 C7 1.338(6) . ?
F8 C7 1.331(6) . ?
F9 C7 1.351(6) . ?
F10 C10 1.317(6) . ?
F11 C10 1.349(6) . ?
F12 C10 1.341(5) . ?
N1 N2 1.353(5) . ?
N1 C1 1.359(5) . ?
N2 C4 1.343(5) . ?
N3 C6 1.349(5) . ?
N3 N4 1.354(4) . ?
N4 C9 1.330(5) . ?
N5 C11 1.341(6) . ?
N5 N6 1.365(5) . ?
N6 C14 1.342(6) . ?
N6 H6 0.87(7) . ?
N7 C16 1.349(6) . ?
N7 N8 1.372(5) . ?
N8 C19 1.338(6) . ?
N8 H8 0.93(5) . ?
C1 C3 1.375(6) . ?
C1 C2 1.492(6) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.482(6) . ?
C6 C8 1.373(6) . ?
C6 C7 1.488(6) . ?
C8 C9 1.395(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.499(6) . ?
C11 C13 1.405(7) . ?
C11 C12 1.491(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.365(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.493(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.395(7) . ?
C16 C17 1.483(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.385(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.497(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
N7 Cu1 N5 177.56(14) . . ?
N7 Cu1 N3 91.17(15) . . ?
N5 Cu1 N3 88.66(15) . . ?
N7 Cu1 N1 89.52(15) . . ?
N5 Cu1 N1 90.53(15) . . ?
N3 Cu1 N1 177.30(13) . . ?
N2 N1 C1 108.1(3) . . ?
N2 N1 Cu1 119.8(3) . . ?
C1 N1 Cu1 132.1(3) . . ?
C4 N2 N1 106.9(3) . . ?
C6 N3 N4 108.1(3) . . ?
C6 N3 Cu1 131.6(3) . . ?
N4 N3 Cu1 119.9(3) . . ?
C9 N4 N3 106.6(3) . . ?
C11 N5 N6 105.4(4) . . ?
C11 N5 Cu1 132.3(3) . . ?
N6 N5 Cu1 122.3(3) . . ?
C14 N6 N5 111.3(4) . . ?
C14 N6 H6 131(4) . . ?
N5 N6 H6 117(4) . . ?
C16 N7 N8 106.0(4) . . ?
C16 N7 Cu1 132.2(3) . . ?
N8 N7 Cu1 121.8(3) . . ?
C19 N8 N7 111.1(3) . . ?
C19 N8 H8 129(3) . . ?
N7 N8 H8 119(3) . . ?
N1 C1 C3 110.2(4) . . ?
N1 C1 C2 122.2(4) . . ?
C3 C1 C2 127.5(4) . . ?
F3 C2 F2 107.3(4) . . ?
F3 C2 F1 107.4(4) . . ?
F2 C2 F1 106.5(4) . . ?
F3 C2 C1 112.2(4) . . ?
F2 C2 C1 112.8(4) . . ?
F1 C2 C1 110.3(4) . . ?
C1 C3 C4 103.3(4) . . ?
C1 C3 H3 128.3 . . ?
C4 C3 H3 128.3 . . ?
N2 C4 C3 111.5(4) . . ?
N2 C4 C5 120.8(4) . . ?
C3 C4 C5 127.7(4) . . ?
F4 C5 F6 105.6(5) . . ?
F4 C5 F5 107.4(5) . . ?
F6 C5 F5 105.9(4) . . ?
F4 C5 C4 112.6(4) . . ?
F6 C5 C4 113.2(3) . . ?
F5 C5 C4 111.6(4) . . ?
N3 C6 C8 110.9(4) . . ?
N3 C6 C7 122.6(4) . . ?
C8 C6 C7 126.5(4) . . ?
F8 C7 F7 107.1(4) . . ?
F8 C7 F9 106.0(4) . . ?
F7 C7 F9 106.9(4) . . ?
F8 C7 C6 114.0(4) . . ?
F7 C7 C6 112.4(4) . . ?
F9 C7 C6 110.1(4) . . ?
C6 C8 C9 102.2(4) . . ?
C6 C8 H8A 128.9 . . ?
C9 C8 H8A 128.9 . . ?
N4 C9 C8 112.2(4) . . ?
N4 C9 C10 120.7(4) . . ?
C8 C9 C10 127.0(4) . . ?
F10 C10 F12 107.6(4) . . ?
F10 C10 F11 107.0(4) . . ?
F12 C10 F11 106.3(4) . . ?
F10 C10 C9 111.6(4) . . ?
F12 C10 C9 111.9(4) . . ?
F11 C10 C9 112.2(4) . . ?
N5 C11 C13 110.0(4) . . ?
N5 C11 C12 122.5(4) . . ?
C13 C11 C12 127.5(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 105.8(4) . . ?
C14 C13 H13 127.1 . . ?
C11 C13 H13 127.1 . . ?
N6 C14 C13 107.5(4) . . ?
N6 C14 C15 122.0(4) . . ?
C13 C14 C15 130.5(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C16 C18 109.4(4) . . ?
N7 C16 C17 122.7(4) . . ?
C18 C16 C17 127.9(4) . . ?
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 . . ?
C19 C18 C16 106.5(4) . . ?
C19 C18 H18 126.8 . . ?
C16 C18 H18 126.8 . . ?
N8 C19 C18 107.0(4) . . ?
N8 C19 C20 122.3(4) . . ?
C18 C19 C20 130.7(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C1 N1 N2 C4 0.0(5) . . . . ?
Cu1 N1 N2 C4 -178.5(3) . . . . ?
C6 N3 N4 C9 1.1(5) . . . . ?
Cu1 N3 N4 C9 174.9(3) . . . . ?
C11 N5 N6 C14 0.3(5) . . . . ?
Cu1 N5 N6 C14 -177.6(3) . . . . ?
C16 N7 N8 C19 1.4(5) . . . . ?
Cu1 N7 N8 C19 -179.8(3) . . . . ?
N2 N1 C1 C3 0.7(5) . . . . ?
Cu1 N1 C1 C3 178.9(3) . . . . ?
N2 N1 C1 C2 177.9(4) . . . . ?
Cu1 N1 C1 C2 -3.9(7) . . . . ?
N1 C1 C2 F3 -26.6(7) . . . . ?
C3 C1 C2 F3 150.1(5) . . . . ?
N1 C1 C2 F2 94.8(6) . . . . ?
C3 C1 C2 F2 -88.6(6) . . . . ?
N1 C1 C2 F1 -146.2(5) . . . . ?
C3 C1 C2 F1 30.4(8) . . . . ?
N1 C1 C3 C4 -1.1(5) . . . . ?
C2 C1 C3 C4 -178.1(5) . . . . ?
N1 N2 C4 C3 -0.7(5) . . . . ?
N1 N2 C4 C5 -179.1(4) . . . . ?
C1 C3 C4 N2 1.1(5) . . . . ?
C1 C3 C4 C5 179.3(5) . . . . ?
N2 C4 C5 F4 103.6(5) . . . . ?
C3 C4 C5 F4 -74.4(7) . . . . ?
N2 C4 C5 F6 -16.1(7) . . . . ?
C3 C4 C5 F6 165.9(5) . . . . ?
N2 C4 C5 F5 -135.5(5) . . . . ?
C3 C4 C5 F5 46.5(7) . . . . ?
N4 N3 C6 C8 -1.1(5) . . . . ?
Cu1 N3 C6 C8 -173.9(3) . . . . ?
N4 N3 C6 C7 178.4(4) . . . . ?
Cu1 N3 C6 C7 5.6(7) . . . . ?
N3 C6 C7 F8 90.7(6) . . . . ?
C8 C6 C7 F8 -89.8(6) . . . . ?
N3 C6 C7 F7 -31.3(7) . . . . ?
C8 C6 C7 F7 148.1(5) . . . . ?
N3 C6 C7 F9 -150.3(4) . . . . ?
C8 C6 C7 F9 29.1(7) . . . . ?
N3 C6 C8 C9 0.6(5) . . . . ?
C7 C6 C8 C9 -178.9(5) . . . . ?
N3 N4 C9 C8 -0.7(5) . . . . ?
N3 N4 C9 C10 -177.0(4) . . . . ?
C6 C8 C9 N4 0.1(6) . . . . ?
C6 C8 C9 C10 176.0(5) . . . . ?
N4 C9 C10 F10 -152.2(5) . . . . ?
C8 C9 C10 F10 32.2(7) . . . . ?
N4 C9 C10 F12 -31.6(6) . . . . ?
C8 C9 C10 F12 152.7(5) . . . . ?
N4 C9 C10 F11 87.8(5) . . . . ?
C8 C9 C10 F11 -87.9(6) . . . . ?
N6 N5 C11 C13 0.1(5) . . . . ?
Cu1 N5 C11 C13 177.7(3) . . . . ?
N6 N5 C11 C12 179.5(4) . . . . ?
Cu1 N5 C11 C12 -2.9(7) . . . . ?
N5 C11 C13 C14 -0.4(5) . . . . ?
C12 C11 C13 C14 -179.8(4) . . . . ?
N5 N6 C14 C13 -0.6(5) . . . . ?
N5 N6 C14 C15 179.3(4) . . . . ?
C11 C13 C14 N6 0.6(5) . . . . ?
C11 C13 C14 C15 -179.3(5) . . . . ?
N8 N7 C16 C18 -1.2(5) . . . . ?
Cu1 N7 C16 C18 -179.8(3) . . . . ?
N8 N7 C16 C17 179.3(4) . . . . ?
Cu1 N7 C16 C17 0.6(7) . . . . ?
N7 C16 C18 C19 0.6(6) . . . . ?
C17 C16 C18 C19 -179.9(5) . . . . ?
N7 N8 C19 C18 -1.0(5) . . . . ?
N7 N8 C19 C20 179.1(4) . . . . ?
C16 C18 C19 N8 0.3(5) . . . . ?
C16 C18 C19 C20 -179.9(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
_geom_hbond_publ_flag
N6 H6 N4 0.87(7) 2.05(7) 2.913(5) 170(7) 2_655 yes
N8 H8 N2 0.93(5) 1.95(5) 2.848(5) 160(5) 2_655 yes

_refine_diff_density_max         0.931
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2430825'
loop_
_audit_author_name
_audit_author_address
'Fedor Dolgushin'
;Kurnakov Institute of general and inorganic chemistry of Russian Academy of Sciences (IGIC RAS)
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Co F12 N8'
_chemical_formula_weight         657.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.466(14)
_cell_length_b                   11.005(16)
_cell_length_c                   14.72(2)
_cell_angle_alpha                109.39(2)
_cell_angle_beta                 101.21(2)
_cell_angle_gamma                91.60(2)
_cell_volume                     1412(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2237
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.90

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             658
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6797
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.204
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             5320
_reflns_number_gt                3367
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+0.1825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5320
_refine_ls_number_parameters     412
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.37110(5) 0.58555(4) 0.74775(4) 0.0538(2) Uani 1 1 d . . . . .
F1 F 0.0513(4) 0.7720(3) 0.8783(3) 0.1281(12) Uani 1 1 d . . . . .
F2 F 0.2706(3) 0.7470(3) 0.9298(2) 0.1150(11) Uani 1 1 d . . . . .
F3 F 0.1058(4) 0.7082(3) 0.9990(2) 0.1145(10) Uani 1 1 d . . . . .
F4 F -0.1913(4) 0.2300(5) 0.6792(8) 0.148(3) Uani 0.748(4) 1 d D . P A 1
F5 F -0.0422(11) 0.1639(6) 0.7729(4) 0.150(3) Uani 0.748(4) 1 d D . P A 1
F6 F -0.0051(6) 0.1517(4) 0.6368(4) 0.1114(16) Uani 0.748(4) 1 d D . P A 1
F4' F 0.0278(15) 0.1394(13) 0.727(2) 0.148(3) Uani 0.252(4) 1 d D . P A 2
F5' F -0.116(3) 0.2066(19) 0.6201(9) 0.150(3) Uani 0.252(4) 1 d D . P A 2
F6' F -0.157(2) 0.2229(14) 0.7587(15) 0.1114(16) Uani 0.252(4) 1 d D . P A 2
F7 F -0.0116(4) 0.6829(6) 0.6425(4) 0.1366(19) Uani 0.849(5) 1 d D . P B 1
F8 F 0.0358(6) 0.7015(5) 0.5142(4) 0.1303(19) Uani 0.849(5) 1 d D . P B 1
F9 F 0.1307(4) 0.5617(3) 0.5724(3) 0.1075(15) Uani 0.849(5) 1 d D . P B 1
F7' F 0.126(3) 0.628(3) 0.5088(11) 0.1366(19) Uani 0.151(5) 1 d D . P B 2
F8' F 0.041(3) 0.608(3) 0.637(2) 0.1303(19) Uani 0.151(5) 1 d D . P B 2
F9' F -0.016(2) 0.7414(18) 0.570(2) 0.1075(15) Uani 0.151(5) 1 d D . P B 2
F10 F 0.3717(9) 1.1708(5) 0.7933(8) 0.142(3) Uani 0.594(5) 1 d D . P C 1
F11 F 0.5177(10) 1.1076(6) 0.7078(5) 0.114(2) Uani 0.594(5) 1 d D . P C 1
F12 F 0.5468(16) 1.0985(8) 0.8535(7) 0.213(6) Uani 0.594(5) 1 d D . P C 1
F10' F 0.5950(8) 1.0668(8) 0.7655(14) 0.142(3) Uani 0.406(5) 1 d D . P C 2
F11' F 0.4882(13) 1.1380(9) 0.8642(4) 0.114(2) Uani 0.406(5) 1 d D . P C 2
F12' F 0.390(2) 1.1562(9) 0.7309(14) 0.213(6) Uani 0.406(5) 1 d D . P C 2
N1 N 0.1980(3) 0.5111(3) 0.7802(2) 0.0541(8) Uani 1 1 d . . . . .
N2 N 0.1457(3) 0.3859(3) 0.7255(2) 0.0558(8) Uani 1 1 d . . . . .
N3 N 0.3297(3) 0.7467(3) 0.7161(2) 0.0562(8) Uani 1 1 d . . . . .
N4 N 0.4286(3) 0.8528(3) 0.7628(2) 0.0604(8) Uani 1 1 d . . . . .
N5 N 0.5476(3) 0.6421(3) 0.8599(2) 0.0562(8) Uani 1 1 d . . . . .
N6 N 0.6094(3) 0.7668(3) 0.8999(3) 0.0588(8) Uani 1 1 d . . . . .
H6 H 0.575(4) 0.824(4) 0.869(3) 0.071(13) Uiso 1 1 d . . . . .
N7 N 0.4245(3) 0.4372(3) 0.6400(2) 0.0576(8) Uani 1 1 d . . . . .
N8 N 0.3333(4) 0.3266(3) 0.5930(3) 0.0618(9) Uani 1 1 d . . . . .
H8 H 0.261(5) 0.320(4) 0.616(3) 0.067(13) Uiso 1 1 d . . . . .
C1 C 0.1118(4) 0.5590(4) 0.8445(3) 0.0577(9) Uani 1 1 d . . . . .
C2 C 0.1357(5) 0.6948(4) 0.9116(3) 0.0729(12) Uani 1 1 d . . . . .
C3 C 0.0020(4) 0.4653(4) 0.8328(3) 0.0654(11) Uani 1 1 d . . . . .
H3A H -0.071757 0.471610 0.867136 0.079 Uiso 1 1 calc R U . . .
C4 C 0.0290(4) 0.3612(4) 0.7579(3) 0.0576(10) Uani 1 1 d . . . . .
C5 C -0.0522(4) 0.2296(4) 0.7126(3) 0.0794(13) Uani 1 1 d D . . . .
C6 C 0.2190(4) 0.7794(4) 0.6576(3) 0.0572(9) Uani 1 1 d . . . . .
C7 C 0.0957(4) 0.6828(4) 0.5964(3) 0.0743(12) Uani 1 1 d D . . . .
C8 C 0.2430(5) 0.9052(4) 0.6653(3) 0.0700(11) Uani 1 1 d . . . . .
H8A H 0.184453 0.951965 0.633631 0.084 Uiso 1 1 calc R U . . .
C9 C 0.3761(5) 0.9477(4) 0.7319(3) 0.0626(10) Uani 1 1 d . . . . .
C10 C 0.4564(5) 1.0759(4) 0.7692(3) 0.0852(14) Uani 1 1 d D . . . .
C11 C 0.6226(4) 0.5794(4) 0.9139(3) 0.0567(9) Uani 1 1 d . . . . .
C12 C 0.5849(5) 0.4368(4) 0.8898(4) 0.0791(13) Uani 1 1 d . . . . .
H12A H 0.481756 0.417147 0.869846 0.119 Uiso 1 1 calc R U . . .
H12B H 0.620040 0.413873 0.947042 0.119 Uiso 1 1 calc R U . . .
H12C H 0.628971 0.388542 0.837127 0.119 Uiso 1 1 calc R U . . .
C13 C 0.7316(5) 0.6641(4) 0.9867(3) 0.0681(11) Uani 1 1 d . . . . .
H13A H 0.799075 0.644284 1.033451 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7196(4) 0.7835(4) 0.9759(3) 0.0612(10) Uani 1 1 d . . . . .
C15 C 0.8035(5) 0.9119(4) 1.0316(4) 0.0893(15) Uani 1 1 d . . . . .
H15A H 0.850706 0.939165 0.988449 0.134 Uiso 1 1 calc R U . . .
H15B H 0.874884 0.905349 1.085392 0.134 Uiso 1 1 calc R U . . .
H15C H 0.739097 0.974165 1.056871 0.134 Uiso 1 1 calc R U . . .
C16 C 0.5410(4) 0.4198(4) 0.5983(3) 0.0667(11) Uani 1 1 d . . . . .
C17 C 0.6655(5) 0.5231(5) 0.6322(4) 0.0923(15) Uani 1 1 d . . . . .
H17A H 0.631157 0.606513 0.657152 0.138 Uiso 1 1 calc R U . . .
H17B H 0.708991 0.519434 0.577755 0.138 Uiso 1 1 calc R U . . .
H17C H 0.736035 0.509583 0.683472 0.138 Uiso 1 1 calc R U . . .
C18 C 0.5204(5) 0.2967(5) 0.5257(4) 0.0828(13) Uani 1 1 d . . . . .
H18A H 0.583910 0.260152 0.485629 0.099 Uiso 1 1 calc R U . . .
C19 C 0.3892(5) 0.2403(4) 0.5249(3) 0.0704(11) Uani 1 1 d . . . . .
C20 C 0.3082(7) 0.1105(5) 0.4645(4) 0.1111(19) Uani 1 1 d . . . . .
H20A H 0.223990 0.099393 0.489318 0.167 Uiso 1 1 calc R U . . .
H20B H 0.369622 0.043656 0.468454 0.167 Uiso 1 1 calc R U . . .
H20C H 0.279174 0.105367 0.396989 0.167 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.008(4) . ?
Co1 N1 2.019(4) . ?
Co1 N7 2.019(4) . ?
Co1 N5 2.023(4) . ?
F1 C2 1.328(5) . ?
F2 C2 1.325(5) . ?
F3 C2 1.333(5) . ?
F4 C5 1.314(4) . ?
F5 C5 1.310(4) . ?
F6 C5 1.326(4) . ?
F4' C5 1.314(5) . ?
F5' C5 1.313(5) . ?
F6' C5 1.315(5) . ?
F7 C7 1.326(4) . ?
F8 C7 1.316(4) . ?
F9 C7 1.329(4) . ?
F7' C7 1.320(5) . ?
F8' C7 1.314(5) . ?
F9' C7 1.315(5) . ?
F10 C10 1.332(5) . ?
F11 C10 1.295(4) . ?
F12 C10 1.306(5) . ?
F10' C10 1.329(5) . ?
F11' C10 1.305(5) . ?
F12' C10 1.310(5) . ?
N1 C1 1.354(5) . ?
N1 N2 1.365(4) . ?
N2 C4 1.340(5) . ?
N3 C6 1.359(5) . ?
N3 N4 1.366(4) . ?
N4 C9 1.343(5) . ?
N5 C11 1.336(5) . ?
N5 N6 1.363(4) . ?
N6 C14 1.332(5) . ?
N6 H6 0.92(4) . ?
N7 C16 1.351(5) . ?
N7 N8 1.362(4) . ?
N8 C19 1.338(5) . ?
N8 H8 0.84(4) . ?
C1 C3 1.387(6) . ?
C1 C2 1.474(6) . ?
C3 C4 1.372(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.493(6) . ?
C6 C8 1.359(6) . ?
C6 C7 1.481(6) . ?
C8 C9 1.396(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.460(6) . ?
C11 C13 1.392(6) . ?
C11 C12 1.504(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.380(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.489(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.400(6) . ?
C16 C17 1.500(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.370(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.500(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N3 Co1 N1 111.46(14) . . ?
N3 Co1 N7 116.23(16) . . ?
N1 Co1 N7 104.73(15) . . ?
N3 Co1 N5 104.16(14) . . ?
N1 Co1 N5 114.16(16) . . ?
N7 Co1 N5 106.31(15) . . ?
C1 N1 N2 108.0(3) . . ?
C1 N1 Co1 134.5(3) . . ?
N2 N1 Co1 117.4(2) . . ?
C4 N2 N1 106.2(3) . . ?
C6 N3 N4 108.2(3) . . ?
C6 N3 Co1 134.4(2) . . ?
N4 N3 Co1 117.4(3) . . ?
C9 N4 N3 106.4(3) . . ?
C11 N5 N6 105.2(3) . . ?
C11 N5 Co1 132.2(2) . . ?
N6 N5 Co1 122.4(2) . . ?
C14 N6 N5 112.2(3) . . ?
C14 N6 H6 130(3) . . ?
N5 N6 H6 117(3) . . ?
C16 N7 N8 106.1(3) . . ?
C16 N7 Co1 133.1(3) . . ?
N8 N7 Co1 120.9(3) . . ?
C19 N8 N7 111.5(4) . . ?
C19 N8 H8 132(3) . . ?
N7 N8 H8 116(3) . . ?
N1 C1 C3 110.3(3) . . ?
N1 C1 C2 121.4(4) . . ?
C3 C1 C2 128.3(4) . . ?
F2 C2 F1 106.5(4) . . ?
F2 C2 F3 106.3(4) . . ?
F1 C2 F3 104.2(4) . . ?
F2 C2 C1 113.5(4) . . ?
F1 C2 C1 113.3(4) . . ?
F3 C2 C1 112.4(4) . . ?
C4 C3 C1 102.9(4) . . ?
C4 C3 H3A 128.6 . . ?
C1 C3 H3A 128.6 . . ?
N2 C4 C3 112.7(3) . . ?
N2 C4 C5 119.1(3) . . ?
C3 C4 C5 128.3(4) . . ?
F5' C5 F4' 114.4(16) . . ?
F5 C5 F4 106.0(5) . . ?
F5' C5 F6' 106.0(14) . . ?
F4' C5 F6' 102.9(13) . . ?
F5 C5 F6 103.0(5) . . ?
F4 C5 F6 105.1(5) . . ?
F5 C5 C4 113.6(4) . . ?
F5' C5 C4 111.4(7) . . ?
F4' C5 C4 112.1(8) . . ?
F4 C5 C4 114.1(4) . . ?
F6' C5 C4 109.5(7) . . ?
F6 C5 C4 114.1(4) . . ?
N3 C6 C8 110.4(4) . . ?
N3 C6 C7 120.5(3) . . ?
C8 C6 C7 129.1(4) . . ?
F8' C7 F9' 102.8(19) . . ?
F8' C7 F7' 118(2) . . ?
F9' C7 F7' 99(2) . . ?
F8 C7 F7 104.9(5) . . ?
F8 C7 F9 107.7(4) . . ?
F7 C7 F9 104.1(4) . . ?
F8' C7 C6 117.8(11) . . ?
F9' C7 C6 110.1(10) . . ?
F8 C7 C6 113.7(4) . . ?
F7' C7 C6 107.3(10) . . ?
F7 C7 C6 112.7(4) . . ?
F9 C7 C6 113.0(3) . . ?
C6 C8 C9 103.9(4) . . ?
C6 C8 H8A 128.1 . . ?
C9 C8 H8A 128.1 . . ?
N4 C9 C8 111.2(3) . . ?
N4 C9 C10 120.2(4) . . ?
C8 C9 C10 128.7(4) . . ?
F11 C10 F12 111.1(8) . . ?
F11' C10 F12' 105.2(9) . . ?
F11' C10 F10' 92.3(9) . . ?
F12' C10 F10' 116.6(12) . . ?
F11 C10 F10 101.4(6) . . ?
F12 C10 F10 100.9(7) . . ?
F11 C10 C9 116.3(4) . . ?
F11' C10 C9 118.8(5) . . ?
F12 C10 C9 113.0(5) . . ?
F12' C10 C9 112.1(7) . . ?
F10' C10 C9 110.8(5) . . ?
F10 C10 C9 112.5(5) . . ?
N5 C11 C13 110.0(4) . . ?
N5 C11 C12 120.1(4) . . ?
C13 C11 C12 129.9(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 106.3(4) . . ?
C14 C13 H13A 126.8 . . ?
C11 C13 H13A 126.8 . . ?
N6 C14 C13 106.3(4) . . ?
N6 C14 C15 121.9(4) . . ?
C13 C14 C15 131.9(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C16 C18 108.6(4) . . ?
N7 C16 C17 121.0(4) . . ?
C18 C16 C17 130.4(4) . . ?
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 . . ?
C19 C18 C16 107.0(4) . . ?
C19 C18 H18A 126.5 . . ?
C16 C18 H18A 126.5 . . ?
N8 C19 C18 106.8(4) . . ?
N8 C19 C20 120.9(4) . . ?
C18 C19 C20 132.3(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C1 N1 N2 C4 0.1(4) . . . . ?
Co1 N1 N2 C4 -177.5(2) . . . . ?
C6 N3 N4 C9 0.0(4) . . . . ?
Co1 N3 N4 C9 -178.6(2) . . . . ?
C11 N5 N6 C14 0.3(4) . . . . ?
Co1 N5 N6 C14 176.8(3) . . . . ?
C16 N7 N8 C19 1.0(4) . . . . ?
Co1 N7 N8 C19 -179.5(3) . . . . ?
N2 N1 C1 C3 0.1(4) . . . . ?
Co1 N1 C1 C3 177.1(3) . . . . ?
N2 N1 C1 C2 -177.2(4) . . . . ?
Co1 N1 C1 C2 -0.2(6) . . . . ?
N1 C1 C2 F2 -24.0(6) . . . . ?
C3 C1 C2 F2 159.1(4) . . . . ?
N1 C1 C2 F1 97.6(5) . . . . ?
C3 C1 C2 F1 -79.2(6) . . . . ?
N1 C1 C2 F3 -144.7(4) . . . . ?
C3 C1 C2 F3 38.5(6) . . . . ?
N1 C1 C3 C4 -0.3(4) . . . . ?
C2 C1 C3 C4 176.8(4) . . . . ?
N1 N2 C4 C3 -0.4(4) . . . . ?
N1 N2 C4 C5 -179.2(3) . . . . ?
C1 C3 C4 N2 0.4(5) . . . . ?
C1 C3 C4 C5 179.2(4) . . . . ?
N2 C4 C5 F5 112.1(7) . . . . ?
C3 C4 C5 F5 -66.6(8) . . . . ?
N2 C4 C5 F5' -67.0(18) . . . . ?
C3 C4 C5 F5' 114.3(18) . . . . ?
N2 C4 C5 F4' 62.5(17) . . . . ?
C3 C4 C5 F4' -116.2(17) . . . . ?
N2 C4 C5 F4 -126.3(7) . . . . ?
C3 C4 C5 F4 55.1(8) . . . . ?
N2 C4 C5 F6' 176.0(13) . . . . ?
C3 C4 C5 F6' -2.6(14) . . . . ?
N2 C4 C5 F6 -5.5(6) . . . . ?
C3 C4 C5 F6 175.8(5) . . . . ?
N4 N3 C6 C8 -0.2(4) . . . . ?
Co1 N3 C6 C8 178.0(3) . . . . ?
N4 N3 C6 C7 179.2(3) . . . . ?
Co1 N3 C6 C7 -2.5(6) . . . . ?
N3 C6 C7 F8' 44(2) . . . . ?
C8 C6 C7 F8' -137(2) . . . . ?
N3 C6 C7 F9' 161.1(19) . . . . ?
C8 C6 C7 F9' -19.5(19) . . . . ?
N3 C6 C7 F8 -149.8(5) . . . . ?
C8 C6 C7 F8 29.6(7) . . . . ?
N3 C6 C7 F7' -93(2) . . . . ?
C8 C6 C7 F7' 87(2) . . . . ?
N3 C6 C7 F7 90.9(5) . . . . ?
C8 C6 C7 F7 -89.7(6) . . . . ?
N3 C6 C7 F9 -26.7(6) . . . . ?
C8 C6 C7 F9 152.7(5) . . . . ?
N3 C6 C8 C9 0.4(4) . . . . ?
C7 C6 C8 C9 -179.1(4) . . . . ?
N3 N4 C9 C8 0.2(4) . . . . ?
N3 N4 C9 C10 179.4(3) . . . . ?
C6 C8 C9 N4 -0.4(5) . . . . ?
C6 C8 C9 C10 -179.5(4) . . . . ?
N4 C9 C10 F11 108.1(7) . . . . ?
C8 C9 C10 F11 -72.8(8) . . . . ?
N4 C9 C10 F11' -57.4(9) . . . . ?
C8 C9 C10 F11' 121.7(8) . . . . ?
N4 C9 C10 F12 -22.1(11) . . . . ?
C8 C9 C10 F12 157.0(10) . . . . ?
N4 C9 C10 F12' 179.6(14) . . . . ?
C8 C9 C10 F12' -1.4(15) . . . . ?
N4 C9 C10 F10' 47.5(11) . . . . ?
C8 C9 C10 F10' -133.4(11) . . . . ?
N4 C9 C10 F10 -135.6(6) . . . . ?
C8 C9 C10 F10 43.4(8) . . . . ?
N6 N5 C11 C13 -0.5(4) . . . . ?
Co1 N5 C11 C13 -176.6(3) . . . . ?
N6 N5 C11 C12 -179.4(3) . . . . ?
Co1 N5 C11 C12 4.6(5) . . . . ?
N5 C11 C13 C14 0.6(5) . . . . ?
C12 C11 C13 C14 179.3(4) . . . . ?
N5 N6 C14 C13 0.1(4) . . . . ?
N5 N6 C14 C15 -179.8(4) . . . . ?
C11 C13 C14 N6 -0.4(4) . . . . ?
C11 C13 C14 C15 179.4(4) . . . . ?
N8 N7 C16 C18 -0.5(4) . . . . ?
Co1 N7 C16 C18 -179.8(3) . . . . ?
N8 N7 C16 C17 -179.8(4) . . . . ?
Co1 N7 C16 C17 0.8(6) . . . . ?
N7 C16 C18 C19 -0.2(5) . . . . ?
C17 C16 C18 C19 179.1(5) . . . . ?
N7 N8 C19 C18 -1.2(5) . . . . ?
N7 N8 C19 C20 179.4(4) . . . . ?
C16 C18 C19 N8 0.8(5) . . . . ?
C16 C18 C19 C20 -179.9(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
_geom_hbond_publ_flag
N6 H6 N4 0.92(4) 1.99(4) 2.813(6) 147(4) . yes
N8 H8 N2 0.83(5) 2.07(4) 2.820(6) 151(4) . yes

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2430827'
loop_
_audit_author_name
_audit_author_address
'Fedor Dolgushin'
;Kurnakov Institute of general and inorganic chemistry of Russian Academy of Sciences (IGIC RAS)
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 Cu2 F12 N8 O4, C H2 Cl2'
_chemical_formula_sum            'C31 H38 Cl2 Cu2 F12 N8 O4'
_chemical_formula_weight         1012.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   20.9937(13)
_cell_length_b                   10.3294(6)
_cell_length_c                   20.7409(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.4360(10)
_cell_angle_gamma                90
_cell_volume                     4291.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9747
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.30

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             2048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.212
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23063
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5679
_reflns_number_gt                4882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+8.3778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5679
_refine_ls_number_parameters     289
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.036
_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 0.07979(2) 0.83196(2) 0.25382(2) 0.02515(9) Uani 1 1 d . . . . .
O1 O 0.14750(8) 0.90875(17) 0.32925(8) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.05948(9) 1.02305(17) 0.33067(10) 0.0427(4) Uani 1 1 d . . . . .
F1 F 0.08381(12) 0.5446(2) 0.07429(12) 0.0846(7) Uani 1 1 d . . . . .
F2 F 0.13588(9) 0.6420(2) 0.16651(9) 0.0624(5) Uani 1 1 d . . . . .
F3 F 0.09642(10) 0.7503(2) 0.07578(10) 0.0693(6) Uani 1 1 d . . . . .
F4 F -0.16594(10) 0.49212(18) 0.10159(11) 0.0703(6) Uani 1 1 d . . . . .
F5 F -0.17150(8) 0.63275(19) 0.17633(10) 0.0563(4) Uani 1 1 d . . . . .
F6 F -0.19562(9) 0.68626(18) 0.07144(10) 0.0601(5) Uani 1 1 d . . . . .
N1 N 0.01439(8) 0.73621(17) 0.17890(8) 0.0256(3) Uani 1 1 d . . . . .
N2 N -0.04909(8) 0.72590(17) 0.18082(8) 0.0255(3) Uani 1 1 d . . . . .
N3 N 0.10749(9) 0.9472(2) 0.19185(10) 0.0367(4) Uani 1 1 d . . . . .
N4 N 0.06254(11) 1.0233(2) 0.14770(12) 0.0458(5) Uani 1 1 d . . . . .
H4 H 0.0200(14) 1.030(3) 0.1524(14) 0.034(7) Uiso 1 1 d . . . . .
C1 C 0.01936(12) 0.6637(2) 0.12691(11) 0.0339(5) Uani 1 1 d . . . . .
C2 C 0.08384(15) 0.6512(3) 0.11091(14) 0.0490(7) Uani 1 1 d . . . . .
C3 C -0.04073(13) 0.6056(2) 0.09427(12) 0.0385(5) Uani 1 1 d . . . . .
H3A H -0.051063 0.549769 0.056133 0.046 Uiso 1 1 calc R U . . .
C4 C -0.08232(12) 0.6481(2) 0.13036(11) 0.0317(4) Uani 1 1 d . . . . .
C5 C -0.15398(13) 0.6159(3) 0.11993(14) 0.0455(6) Uani 1 1 d . . . . .
C6 C 0.16772(13) 0.9786(3) 0.18638(15) 0.0533(7) Uani 1 1 d . . . . .
C7 C 0.22968(14) 0.9116(4) 0.22669(18) 0.0642(9) Uani 1 1 d . . . . .
H7A H 0.218767 0.850268 0.257860 0.096 Uiso 1 1 calc R U . . .
H7B H 0.261681 0.975646 0.252513 0.096 Uiso 1 1 calc R U . . .
H7C H 0.249347 0.864761 0.196218 0.096 Uiso 1 1 calc R U . . .
C8 C 0.15966(17) 1.0769(5) 0.1384(2) 0.0808(13) Uani 1 1 d . . . . .
H8A H 0.194149 1.117701 0.124901 0.097 Uiso 1 1 calc R U . . .
C9 C 0.09270(18) 1.1036(4) 0.11452(19) 0.0727(11) Uani 1 1 d . . . . .
C10 C 0.0541(3) 1.1982(6) 0.0631(3) 0.112(2) Uani 1 1 d . . . . .
H10A H 0.018755 1.236949 0.078766 0.168 Uiso 1 1 calc R U . . .
H10B H 0.034033 1.153315 0.020148 0.168 Uiso 1 1 calc R U . . .
H10C H 0.084082 1.266262 0.056622 0.168 Uiso 1 1 calc R U . . .
C11 C 0.12062(11) 0.9985(2) 0.35383(11) 0.0335(5) Uani 1 1 d . . . . .
C12 C 0.16644(17) 1.0753(3) 0.41189(15) 0.0645(9) Uani 1 1 d D . . . .
C13 C 0.1568(3) 1.0097(5) 0.4771(2) 0.0646(12) Uani 0.615(4) 1 d D . P A 1
H13A H 0.109959 1.016837 0.476036 0.097 Uiso 0.615(4) 1 calc R U P A 1
H13B H 0.185175 1.053343 0.517479 0.097 Uiso 0.615(4) 1 calc R U P A 1
H13C H 0.169330 0.918105 0.478277 0.097 Uiso 0.615(4) 1 calc R U P A 1
C14 C 0.1381(5) 1.2110(5) 0.4132(4) 0.136(5) Uani 0.615(4) 1 d D . P A 1
H14A H 0.092180 1.204716 0.415196 0.205 Uiso 0.615(4) 1 calc R U P A 1
H14B H 0.138547 1.257865 0.372267 0.205 Uiso 0.615(4) 1 calc R U P A 1
H14C H 0.165514 1.257604 0.453077 0.205 Uiso 0.615(4) 1 calc R U P A 1
C15 C 0.2400(2) 1.0450(10) 0.4204(4) 0.107(3) Uani 0.615(4) 1 d D . P A 1
H15A H 0.245805 0.951213 0.417796 0.161 Uiso 0.615(4) 1 calc R U P A 1
H15B H 0.267609 1.076751 0.464425 0.161 Uiso 0.615(4) 1 calc R U P A 1
H15C H 0.253562 1.087687 0.384403 0.161 Uiso 0.615(4) 1 calc R U P A 1
C13' C 0.1994(5) 1.1707(8) 0.3719(4) 0.0646(12) Uani 0.385(4) 1 d D . P A 2
H13D H 0.164522 1.222767 0.340637 0.097 Uiso 0.385(4) 1 calc R U P A 2
H13E H 0.223343 1.120788 0.346332 0.097 Uiso 0.385(4) 1 calc R U P A 2
H13F H 0.230724 1.227942 0.403840 0.097 Uiso 0.385(4) 1 calc R U P A 2
C14' C 0.2274(6) 0.9988(10) 0.4530(6) 0.136(5) Uani 0.385(4) 1 d D . P A 2
H14D H 0.213141 0.930793 0.478594 0.205 Uiso 0.385(4) 1 calc R U P A 2
H14E H 0.258558 1.057230 0.484317 0.205 Uiso 0.385(4) 1 calc R U P A 2
H14F H 0.249453 0.959409 0.422371 0.205 Uiso 0.385(4) 1 calc R U P A 2
C15' C 0.1292(5) 1.1736(12) 0.4425(7) 0.107(3) Uani 0.385(4) 1 d D . P A 2
H15D H 0.112747 1.130729 0.476564 0.161 Uiso 0.385(4) 1 calc R U P A 2
H15E H 0.091471 1.209250 0.406849 0.161 Uiso 0.385(4) 1 calc R U P A 2
H15F H 0.159677 1.243838 0.463845 0.161 Uiso 0.385(4) 1 calc R U P A 2
C1S C 0.000000 0.2870(6) 0.250000 0.104(3) Uani 1 2 d S T P . .
H1SA H 0.020040 0.232435 0.288060 0.125 Uiso 1 1 d R U . . .
Cl1S Cl 0.06064(11) 0.37975(18) 0.23286(8) 0.1472(8) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9402(16) . ?
Cu1 N3 1.9632(19) . ?
Cu1 N2 1.9942(17) 2 ?
Cu1 N1 1.9998(17) . ?
O1 C11 1.269(3) . ?
O2 C11 1.254(3) . ?
F1 C2 1.338(3) . ?
F2 C2 1.333(3) . ?
F3 C2 1.328(4) . ?
F4 C5 1.336(3) . ?
F5 C5 1.339(3) . ?
F6 C5 1.333(3) . ?
N1 C1 1.343(3) . ?
N1 N2 1.349(2) . ?
N2 C4 1.338(3) . ?
N3 C6 1.343(3) . ?
N3 N4 1.353(3) . ?
N4 C9 1.351(4) . ?
N4 H4 0.93(3) . ?
C1 C3 1.378(4) . ?
C1 C2 1.493(4) . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.492(3) . ?
C6 C8 1.395(4) . ?
C6 C7 1.490(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.371(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.494(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.520(3) . ?
C12 C14 1.526(5) . ?
C12 C14' 1.527(5) . ?
C12 C15' 1.531(5) . ?
C12 C15 1.533(5) . ?
C12 C13' 1.575(5) . ?
C12 C13 1.579(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13' H13D 0.9800 . ?
C13' H13E 0.9800 . ?
C13' H13F 0.9800 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C1S Cl1S 1.713(4) . ?
C1S Cl1S 1.714(4) 2 ?
C1S H1SA 0.9587 . ?
C1S H1SA 0.9587 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 89.48(8) . . ?
O1 Cu1 N2 89.11(7) . 2 ?
N3 Cu1 N2 175.95(8) . 2 ?
O1 Cu1 N1 174.41(7) . . ?
N3 Cu1 N1 93.45(8) . . ?
N2 Cu1 N1 88.28(7) 2 . ?
C11 O1 Cu1 108.43(14) . . ?
C1 N1 N2 107.14(18) . . ?
C1 N1 Cu1 134.39(15) . . ?
N2 N1 Cu1 118.06(12) . . ?
C4 N2 N1 108.20(17) . . ?
C4 N2 Cu1 131.51(15) . 2 ?
N1 N2 Cu1 119.99(13) . 2 ?
C6 N3 N4 106.6(2) . . ?
C6 N3 Cu1 132.31(18) . . ?
N4 N3 Cu1 120.81(15) . . ?
C9 N4 N3 111.3(2) . . ?
C9 N4 H4 128.1(17) . . ?
N3 N4 H4 118.1(17) . . ?
N1 C1 C3 111.0(2) . . ?
N1 C1 C2 121.4(2) . . ?
C3 C1 C2 127.7(2) . . ?
F3 C2 F2 106.5(3) . . ?
F3 C2 F1 106.8(2) . . ?
F2 C2 F1 107.1(3) . . ?
F3 C2 C1 113.5(2) . . ?
F2 C2 C1 112.1(2) . . ?
F1 C2 C1 110.5(3) . . ?
C1 C3 C4 103.3(2) . . ?
C1 C3 H3A 128.4 . . ?
C4 C3 H3A 128.4 . . ?
N2 C4 C3 110.4(2) . . ?
N2 C4 C5 120.9(2) . . ?
C3 C4 C5 128.6(2) . . ?
F6 C5 F4 106.4(2) . . ?
F6 C5 F5 107.4(2) . . ?
F4 C5 F5 107.2(2) . . ?
F6 C5 C4 113.1(2) . . ?
F4 C5 C4 110.5(2) . . ?
F5 C5 C4 111.9(2) . . ?
N3 C6 C8 108.7(3) . . ?
N3 C6 C7 121.7(3) . . ?
C8 C6 C7 129.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C6 107.2(3) . . ?
C9 C8 H8A 126.4 . . ?
C6 C8 H8A 126.4 . . ?
N4 C9 C8 106.2(3) . . ?
N4 C9 C10 121.9(3) . . ?
C8 C9 C10 131.9(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 121.4(2) . . ?
O2 C11 C12 122.0(2) . . ?
O1 C11 C12 116.6(2) . . ?
C11 C12 C14 109.7(4) . . ?
C11 C12 C14' 113.4(5) . . ?
C11 C12 C15' 113.2(5) . . ?
C14' C12 C15' 123.9(7) . . ?
C11 C12 C15 111.2(3) . . ?
C14 C12 C15 124.7(6) . . ?
C11 C12 C13' 100.5(4) . . ?
C14' C12 C13' 101.0(8) . . ?
C15' C12 C13' 99.4(7) . . ?
C11 C12 C13 104.0(3) . . ?
C14 C12 C13 103.2(5) . . ?
C15 C12 C13 101.4(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13' H13D 109.5 . . ?
C12 C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12 C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C12 C14' H14D 109.5 . . ?
C12 C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C12 C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C12 C15' H15D 109.5 . . ?
C12 C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C12 C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
Cl1S C1S Cl1S 112.0(4) . 2 ?
Cl1S C1S H1SA 109.2 . . ?
Cl1S C1S H1SA 109.1 2 . ?
Cl1S C1S H1SA 109.15(11) . 2 ?
Cl1S C1S H1SA 109.24(10) 2 2 ?
H1SA C1S H1SA 107.9 . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C4 -0.2(2) . . . . ?
Cu1 N1 N2 C4 -173.87(14) . . . . ?
C1 N1 N2 Cu1 -174.61(14) . . . 2 ?
Cu1 N1 N2 Cu1 11.67(19) . . . 2 ?
C6 N3 N4 C9 -0.6(4) . . . . ?
Cu1 N3 N4 C9 174.1(3) . . . . ?
N2 N1 C1 C3 0.2(3) . . . . ?
Cu1 N1 C1 C3 172.39(17) . . . . ?
N2 N1 C1 C2 -178.9(2) . . . . ?
Cu1 N1 C1 C2 -6.7(4) . . . . ?
N1 C1 C2 F3 -81.1(3) . . . . ?
C3 C1 C2 F3 100.0(3) . . . . ?
N1 C1 C2 F2 39.5(4) . . . . ?
C3 C1 C2 F2 -139.4(3) . . . . ?
N1 C1 C2 F1 158.9(2) . . . . ?
C3 C1 C2 F1 -20.0(4) . . . . ?
N1 C1 C3 C4 -0.1(3) . . . . ?
C2 C1 C3 C4 178.9(2) . . . . ?
N1 N2 C4 C3 0.1(2) . . . . ?
Cu1 N2 C4 C3 173.68(16) 2 . . . ?
N1 N2 C4 C5 179.0(2) . . . . ?
Cu1 N2 C4 C5 -7.4(3) 2 . . . ?
C1 C3 C4 N2 0.0(3) . . . . ?
C1 C3 C4 C5 -178.8(2) . . . . ?
N2 C4 C5 F6 99.6(3) . . . . ?
C3 C4 C5 F6 -81.8(3) . . . . ?
N2 C4 C5 F4 -141.3(2) . . . . ?
C3 C4 C5 F4 37.4(4) . . . . ?
N2 C4 C5 F5 -21.9(3) . . . . ?
C3 C4 C5 F5 156.8(2) . . . . ?
N4 N3 C6 C8 0.6(4) . . . . ?
Cu1 N3 C6 C8 -173.1(3) . . . . ?
N4 N3 C6 C7 -178.5(3) . . . . ?
Cu1 N3 C6 C7 7.7(5) . . . . ?
N3 C6 C8 C9 -0.5(5) . . . . ?
C7 C6 C8 C9 178.6(4) . . . . ?
N3 N4 C9 C8 0.3(5) . . . . ?
N3 N4 C9 C10 -179.7(4) . . . . ?
C6 C8 C9 N4 0.1(5) . . . . ?
C6 C8 C9 C10 -179.9(5) . . . . ?
Cu1 O1 C11 O2 1.9(3) . . . . ?
Cu1 O1 C11 C12 -177.33(18) . . . . ?
O2 C11 C12 C14 -26.2(6) . . . . ?
O1 C11 C12 C14 153.0(5) . . . . ?
O2 C11 C12 C14' 153.7(8) . . . . ?
O1 C11 C12 C14' -27.1(8) . . . . ?
O2 C11 C12 C15' 5.7(8) . . . . ?
O1 C11 C12 C15' -175.0(7) . . . . ?
O2 C11 C12 C15 -168.1(5) . . . . ?
O1 C11 C12 C15 11.1(5) . . . . ?
O2 C11 C12 C13' -99.3(5) . . . . ?
O1 C11 C12 C13' 79.9(5) . . . . ?
O2 C11 C12 C13 83.6(4) . . . . ?
O1 C11 C12 C13 -97.2(3) . . . . ?

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
_geom_hbond_publ_flag
N4 H4 O2 0.93(3) 1.81(3) 2.730(3) 172(3) 2_555 yes
C1S H1SA O2 0.9600 2.3900 3.247(6) 149.00 1_545 yes

_refine_diff_density_max         0.998
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.070

