# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_CuA
_database_code_depnum_ccdc_archive 'CCDC 2077016'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet-Ladeira'
;CNRS
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-26 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         'C18 H22 Br4 Cu2 F2 N4'
_chemical_formula_sum            'C18 H22 Br4 Cu2 F2 N4'
_chemical_formula_weight         779.10

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'
Br Br -0.2901 2.4595 '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                   7.8883(6)
_cell_length_b                   8.1714(7)
_cell_length_c                   10.3538(8)
_cell_angle_alpha                71.537(2)
_cell_angle_beta                 79.335(2)
_cell_angle_gamma                70.634(3)
_cell_volume                     594.83(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.22

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_F_000             374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    8.534
_shelx_estimated_absorpt_T_min   0.224
_shelx_estimated_absorpt_T_max   0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4616
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16362
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2720
_reflns_number_gt                2338
_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    'SHELXT (Sheldrick 2015)'
_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)+(0.0136P)²+0.5897P] 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         2720
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.46642(4) 0.78358(4) 0.58999(3) 0.02159(8) Uani 1 1 d . . . . .
Br1 Br 0.74491(3) 0.86109(4) 0.50101(3) 0.02598(7) Uani 1 1 d . . . . .
Br2 Br 0.52132(4) 0.74356(4) 0.81864(3) 0.03326(8) Uani 1 1 d . . . . .
F1 F 0.1027(2) 0.6110(2) 0.31238(17) 0.0373(4) Uani 1 1 d . . . . .
N1 N 0.4400(3) 0.7457(3) 0.4076(2) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.2497(3) 0.6851(3) 0.6468(2) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.5318(4) 0.7884(4) 0.2864(3) 0.0257(6) Uani 1 1 d . . . . .
H1 H 0.632110 0.830995 0.280336 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4857(4) 0.7727(4) 0.1687(3) 0.0279(6) Uani 1 1 d . . . . .
H2 H 0.553765 0.805043 0.083883 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3421(4) 0.7104(4) 0.1748(3) 0.0286(6) Uani 1 1 d . . . . .
H3 H 0.309409 0.696635 0.095873 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2474(3) 0.6689(4) 0.3008(3) 0.0260(6) Uani 1 1 d . . . . .
C5 C 0.2962(3) 0.6864(3) 0.4156(2) 0.0212(5) Uani 1 1 d . . . . .
C6 C 0.1999(3) 0.6488(3) 0.5520(3) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.102552 0.598595 0.568943 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1469(4) 0.6549(4) 0.7819(3) 0.0290(6) Uani 1 1 d . . . . .
H7A H 0.231720 0.587508 0.853390 0.035 Uiso 1 1 calc R U . . .
H7B H 0.068244 0.580742 0.785607 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0323(4) 0.8315(4) 0.8104(3) 0.0337(7) Uani 1 1 d . . . . .
H8A H -0.057280 0.896454 0.742001 0.040 Uiso 1 1 calc R U . . .
H8B H 0.109715 0.908494 0.802685 0.040 Uiso 1 1 calc R U . . .
C9 C -0.0651(4) 0.7958(5) 0.9537(3) 0.0397(7) Uani 1 1 d . . . . .
H9A H -0.147182 0.725813 0.959298 0.060 Uiso 1 1 calc R U . . .
H9B H -0.134246 0.910912 0.972939 0.060 Uiso 1 1 calc R U . . .
H9C H 0.023673 0.727682 1.020878 0.060 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 N2 2.039(2) . ?
Cu1 N1 2.065(2) . ?
Cu1 Br2 2.3862(4) . ?
Cu1 Br1 2.4249(4) . ?
Cu1 Br1 2.7813(5) 2_676 ?
Cu1 Cu1 3.6008(7) 2_676 ?
F1 C4 1.347(3) . ?
N1 C1 1.331(3) . ?
N1 C5 1.354(3) . ?
N2 C6 1.269(3) . ?
N2 C7 1.472(3) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C5 C6 1.465(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
N2 Cu1 N1 80.11(8) . . ?
N2 Cu1 Br2 94.48(6) . . ?
N1 Cu1 Br2 165.05(6) . . ?
N2 Cu1 Br1 170.04(6) . . ?
N1 Cu1 Br1 92.33(6) . . ?
Br2 Cu1 Br1 91.240(14) . . ?
N2 Cu1 Br1 93.48(6) . 2_676 ?
N1 Cu1 Br1 88.27(6) . 2_676 ?
Br2 Cu1 Br1 106.057(15) . 2_676 ?
Br1 Cu1 Br1 92.761(13) . 2_676 ?
Cu1 Br1 Cu1 87.238(13) . 2_676 ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cu1 128.78(17) . . ?
C5 N1 Cu1 112.13(16) . . ?
C6 N2 C7 118.0(2) . . ?
C6 N2 Cu1 114.37(17) . . ?
C7 N2 Cu1 127.58(17) . . ?
N1 C1 C2 122.2(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
F1 C4 C5 118.8(2) . . ?
F1 C4 C3 119.5(2) . . ?
C5 C4 C3 121.6(2) . . ?
N1 C5 C4 120.5(2) . . ?
N1 C5 C6 114.8(2) . . ?
C4 C5 C6 124.7(2) . . ?
N2 C6 C5 118.4(2) . . ?
N2 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C8 111.4(2) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.0(2) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2077019'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet-Ladeira'
;CNRS
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C9 H7 F N2'
_chemical_formula_sum            'C9 H7 F N2'
_chemical_formula_weight         162.17

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9462(8)
_cell_length_b                   11.8055(9)
_cell_length_c                   7.1741(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.811(5)
_cell_angle_gamma                90
_cell_volume                     792.53(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.15

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_T_max  0.7465

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_number            17537
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             1444
_reflns_number_gt                1236
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1361P)²+0.8422P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1444
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2555
_refine_ls_wR_factor_gt          0.2489
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4684(3) 0.3596(3) 0.3481(5) 0.0371(8) Uani 1 1 d . . . . .
H1 H 0.416747 0.428399 0.311021 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3981(3) 0.2595(3) 0.2767(4) 0.0375(8) Uani 1 1 d . . . . .
H2 H 0.301298 0.260067 0.191334 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4706(3) 0.1588(3) 0.3314(5) 0.0385(8) Uani 1 1 d . . . . .
H3 H 0.426204 0.087928 0.286239 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6101(3) 0.1659(3) 0.4545(5) 0.0335(8) Uani 1 1 d . . . . .
C5 C 0.6774(3) 0.2684(2) 0.5207(4) 0.0290(7) Uani 1 1 d . . . . .
C6 C 0.8256(3) 0.2725(3) 0.6535(4) 0.0326(7) Uani 1 1 d . . . . .
H6 H 0.867035 0.202283 0.708611 0.039 Uiso 1 1 calc R U . . .
C7 C 0.9100(3) 0.3642(3) 0.7067(4) 0.0325(7) Uani 1 1 d . . . . .
C8 C 1.0600(4) 0.3589(3) 0.8524(5) 0.0453(9) Uani 1 1 d . . . . .
H8A H 1.08463 0.280138 0.892562 0.068 Uiso 1 1 calc R U . . .
H8B H 1.066515 0.404601 0.969223 0.068 Uiso 1 1 calc R U . . .
H8C H 1.126648 0.388632 0.790311 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8661(3) 0.4755(3) 0.6270(5) 0.0367(8) Uani 1 1 d . . . . .
F1 F 0.6863(2) 0.06923(15) 0.5114(3) 0.0513(7) Uani 1 1 d . . . . .
N1 N 0.6042(3) 0.3655(2) 0.4655(4) 0.0333(7) Uani 1 1 d . . . . .
N2 N 0.8492(3) 0.5680(2) 0.5757(5) 0.0538(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.329(4) . ?
C1 C2 1.380(5) . ?
C1 H1 0.95 . ?
C2 C3 1.377(5) . ?
C2 H2 0.95 . ?
C3 C4 1.372(5) . ?
C3 H3 0.95 . ?
C4 F1 1.355(3) . ?
C4 C5 1.386(4) . ?
C5 N1 1.344(4) . ?
C5 C6 1.459(4) . ?
C6 C7 1.345(4) . ?
C6 H6 0.95 . ?
C7 C9 1.440(4) . ?
C7 C8 1.505(4) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N2 1.146(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.9(3) . . ?
N1 C1 H1 118 . . ?
C2 C1 H1 118 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
F1 C4 C3 118.9(3) . . ?
F1 C4 C5 118.4(3) . . ?
C3 C4 C5 122.7(3) . . ?
N1 C5 C4 119.5(3) . . ?
N1 C5 C6 119.4(3) . . ?
C4 C5 C6 121.1(3) . . ?
C7 C6 C5 127.4(3) . . ?
C7 C6 H6 116.3 . . ?
C5 C6 H6 116.3 . . ?
C6 C7 C9 123.1(3) . . ?
C6 C7 C8 122.7(3) . . ?
C9 C7 C8 114.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C7 171.2(3) . . ?
C1 N1 C5 118.4(3) . . ?


# start Validation Reply Form
_vrf_PLAT930_4                   
;
PROBLEM: FCF-based   Twin Law ( 1 0 0)[ 2 0 1] Est.d BASF       0.17 Check,
RESPONSE: "TwinRotMat" -an option in PLATON- was run, the resulting twin law 
and the BASF value were refined, but the R-value did not decrease. 
The same procedure was performed with the CELL NOW program in APEX3, 
the different domains were not identified. Therefore, we assume that this 
alert is given by the low quality of the data.

;

# end Validation Reply Form

# END of CIF

####################################################################### 
# 
# 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_Cu4B
_database_code_depnum_ccdc_archive 'CCDC 2077017'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet-Ladeira'
;CNRS
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C72 H108 Cl6 Cu4 F4 N8 O1'
_chemical_formula_sum            'C72 H108 Cl6 Cu4 F4 N8 O'
_chemical_formula_weight         1644.56
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_Int_Tables_number      82
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   11.5858(4)
_cell_length_b                   11.5858(4)
_cell_length_c                   29.2335(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3924.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3719
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      23.69

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1716
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_T_max  0.7454

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_number            15162
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.994
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.952
_reflns_number_total             4023
_reflns_number_gt                3122
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.1313P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     316
_refine_ls_number_restraints     386
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(9)
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5964(6) 0.2656(6) 0.1303(3) 0.0431(17) Uani 1 1 d . . . . .
H1 H 0.58033 0.20294 0.110367 0.052 Uiso 1 1 calc R U . . .
C2 C 0.6244(5) 0.3771(6) 0.1169(3) 0.0420(17) Uani 1 1 d . . . . .
C3 C 0.6379(6) 0.4374(8) 0.0756(3) 0.054(2) Uani 1 1 d . . . . .
C4 C 0.6608(7) 0.5518(7) 0.0747(3) 0.061(2) Uani 1 1 d . . . . .
H4 H 0.668001 0.591863 0.046537 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6738(6) 0.6101(7) 0.1167(3) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.690947 0.690275 0.116372 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6630(6) 0.5570(6) 0.1568(3) 0.0439(18) Uani 1 1 d . . . . .
H6 H 0.671757 0.598339 0.184693 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6218(5) 0.3658(5) 0.1927(2) 0.0329(15) Uani 1 1 d D . . . .
C8 C 0.633(3) 0.406(6) 0.2410(7) 0.038(4) Uani 0.610(11) 1 d D U P A 1
H8A H 0.596909 0.347845 0.261108 0.046 Uiso 0.610(11) 1 calc R U P A 1
H8B H 0.588152 0.478443 0.244254 0.046 Uiso 0.610(11) 1 calc R U P A 1
C9 C 0.755(3) 0.429(3) 0.2585(7) 0.047(3) Uani 0.610(11) 1 d D U P A 1
H9A H 0.799266 0.35568 0.258807 0.056 Uiso 0.610(11) 1 calc R U P A 1
H9B H 0.794927 0.483298 0.237731 0.056 Uiso 0.610(11) 1 calc R U P A 1
C10 C 0.7521(15) 0.4782(15) 0.3056(5) 0.062(3) Uani 0.610(11) 1 d D U P A 1
H10A H 0.708317 0.425119 0.325656 0.074 Uiso 0.610(11) 1 calc R U P A 1
H10B H 0.709927 0.552505 0.30468 0.074 Uiso 0.610(11) 1 calc R U P A 1
C11 C 0.8739(14) 0.4991(12) 0.3269(5) 0.069(3) Uani 0.610(11) 1 d D U P A 1
H11A H 0.910639 0.423102 0.332338 0.082 Uiso 0.610(11) 1 calc R U P A 1
H11B H 0.921855 0.540696 0.304254 0.082 Uiso 0.610(11) 1 calc R U P A 1
C12 C 0.8759(18) 0.5670(14) 0.3717(5) 0.082(4) Uani 0.610(11) 1 d D U P A 1
H12A H 0.955942 0.591751 0.378274 0.099 Uiso 0.610(11) 1 calc R U P A 1
H12B H 0.827901 0.637183 0.36831 0.099 Uiso 0.610(11) 1 calc R U P A 1
C13 C 0.832(2) 0.4981(18) 0.4106(6) 0.094(4) Uani 0.610(11) 1 d D U P A 1
H13A H 0.887903 0.435203 0.416728 0.113 Uiso 0.610(11) 1 calc R U P A 1
H13B H 0.758533 0.461655 0.401247 0.113 Uiso 0.610(11) 1 calc R U P A 1
C14 C 0.811(2) 0.567(2) 0.4574(6) 0.101(4) Uani 0.610(11) 1 d D U P A 1
H14A H 0.884744 0.599702 0.467915 0.121 Uiso 0.610(11) 1 calc R U P A 1
H14B H 0.757298 0.631759 0.451282 0.121 Uiso 0.610(11) 1 calc R U P A 1
C15 C 0.760(2) 0.493(2) 0.4957(6) 0.106(4) Uani 0.610(11) 1 d D U P A 1
H15A H 0.80129 0.417678 0.495927 0.127 Uiso 0.610(11) 1 calc R U P A 1
H15B H 0.678216 0.476392 0.48831 0.127 Uiso 0.610(11) 1 calc R U P A 1
C16 C 0.766(3) 0.544(2) 0.5445(7) 0.107(5) Uani 0.610(11) 1 d D U P A 1
H16A H 0.84669 0.545846 0.555074 0.129 Uiso 0.610(11) 1 calc R U P A 1
H16B H 0.736651 0.624741 0.54386 0.129 Uiso 0.610(11) 1 calc R U P A 1
C17 C 0.693(3) 0.474(2) 0.5775(8) 0.114(5) Uani 0.610(11) 1 d D U P A 1
H17A H 0.719902 0.392426 0.576363 0.136 Uiso 0.610(11) 1 calc R U P A 1
H17B H 0.612017 0.475263 0.567215 0.136 Uiso 0.610(11) 1 calc R U P A 1
C18 C 0.699(3) 0.516(3) 0.6270(8) 0.128(7) Uani 0.610(11) 1 d D U P A 1
H18A H 0.710828 0.599706 0.62737 0.193 Uiso 0.610(11) 1 calc R U P A 1
H18B H 0.763593 0.478073 0.642725 0.193 Uiso 0.610(11) 1 calc R U P A 1
H18C H 0.626781 0.497105 0.642662 0.193 Uiso 0.610(11) 1 calc R U P A 1
C8' C 0.634(5) 0.397(9) 0.2420(11) 0.041(5) Uani 0.390(11) 1 d D U P A 2
H8C H 0.601781 0.335163 0.261369 0.049 Uiso 0.390(11) 1 calc R U P A 2
H8D H 0.591275 0.469209 0.248385 0.049 Uiso 0.390(11) 1 calc R U P A 2
C9' C 0.762(5) 0.414(5) 0.2538(11) 0.047(4) Uani 0.390(11) 1 d D U P A 2
H9C H 0.805761 0.345843 0.243714 0.056 Uiso 0.390(11) 1 calc R U P A 2
H9D H 0.791418 0.482038 0.23675 0.056 Uiso 0.390(11) 1 calc R U P A 2
C10' C 0.782(3) 0.433(2) 0.3033(8) 0.058(4) Uani 0.390(11) 1 d D U P A 2
H10C H 0.865685 0.440096 0.308714 0.069 Uiso 0.390(11) 1 calc R U P A 2
H10D H 0.754456 0.363762 0.32017 0.069 Uiso 0.390(11) 1 calc R U P A 2
C11' C 0.720(2) 0.5413(19) 0.3230(8) 0.070(4) Uani 0.390(11) 1 d D U P A 2
H11C H 0.722785 0.603366 0.299734 0.084 Uiso 0.390(11) 1 calc R U P A 2
H11D H 0.637847 0.522187 0.328328 0.084 Uiso 0.390(11) 1 calc R U P A 2
C12' C 0.771(3) 0.587(2) 0.3671(7) 0.083(4) Uani 0.390(11) 1 d D U P A 2
H12C H 0.85102 0.612015 0.360572 0.1 Uiso 0.390(11) 1 calc R U P A 2
H12D H 0.726803 0.656365 0.375954 0.1 Uiso 0.390(11) 1 calc R U P A 2
C13' C 0.775(3) 0.509(3) 0.4071(8) 0.094(5) Uani 0.390(11) 1 d D U P A 2
H13C H 0.806539 0.433065 0.397613 0.113 Uiso 0.390(11) 1 calc R U P A 2
H13D H 0.695225 0.495825 0.418448 0.113 Uiso 0.390(11) 1 calc R U P A 2
C14' C 0.853(3) 0.561(3) 0.4482(9) 0.102(5) Uani 0.390(11) 1 d D U P A 2
H14C H 0.935879 0.551782 0.440753 0.123 Uiso 0.390(11) 1 calc R U P A 2
H14D H 0.836467 0.643919 0.452173 0.123 Uiso 0.390(11) 1 calc R U P A 2
C15' C 0.824(3) 0.495(3) 0.4927(9) 0.109(5) Uani 0.390(11) 1 d D U P A 2
H15C H 0.888699 0.441512 0.499919 0.131 Uiso 0.390(11) 1 calc R U P A 2
H15D H 0.75432 0.447109 0.487589 0.131 Uiso 0.390(11) 1 calc R U P A 2
C16' C 0.803(4) 0.577(3) 0.5350(11) 0.113(5) Uani 0.390(11) 1 d D U P A 2
H16C H 0.876526 0.598408 0.549928 0.136 Uiso 0.390(11) 1 calc R U P A 2
H16D H 0.761442 0.647774 0.525755 0.136 Uiso 0.390(11) 1 calc R U P A 2
C17' C 0.730(4) 0.503(4) 0.5660(13) 0.117(6) Uani 0.390(11) 1 d D U P A 2
H17C H 0.658456 0.481231 0.549342 0.141 Uiso 0.390(11) 1 calc R U P A 2
H17D H 0.772348 0.430553 0.572581 0.141 Uiso 0.390(11) 1 calc R U P A 2
C18' C 0.695(5) 0.557(4) 0.6109(13) 0.136(9) Uani 0.390(11) 1 d D U P A 2
H18D H 0.749207 0.619434 0.618256 0.204 Uiso 0.390(11) 1 calc R U P A 2
H18E H 0.697978 0.498386 0.635083 0.204 Uiso 0.390(11) 1 calc R U P A 2
H18F H 0.61704 0.587861 0.608429 0.204 Uiso 0.390(11) 1 calc R U P A 2
N1 N 0.5958(4) 0.2613(5) 0.1765(2) 0.0376(13) Uani 1 1 d . . . . .
N2 N 0.6381(4) 0.4383(4) 0.1570(2) 0.0353(13) Uani 1 1 d . . . . .
O1 O 0.5 0 0.25 0.034(2) Uani 1 4 d S T P . .
F1 F 0.6235(4) 0.3762(5) 0.03720(16) 0.0735(15) Uani 1 1 d . . . . .
Cl1 Cl 0.5 0 0.15038(12) 0.0984(15) Uani 1 2 d S T P . .
Cl2 Cl 0.72535(14) 0.11514(14) 0.25391(8) 0.0569(6) Uani 1 1 d . . . . .
Cu1 Cu 0.54892(6) 0.12627(6) 0.21282(3) 0.0369(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.351(9) . ?
C1 C2 1.388(10) . ?
C1 H1 0.95 . ?
C2 N2 1.380(9) . ?
C2 C3 1.405(11) . ?
C3 F1 1.337(9) . ?
C3 C4 1.352(11) . ?
C4 C5 1.409(12) . ?
C4 H4 0.95 . ?
C5 C6 1.330(10) . ?
C5 H5 0.95 . ?
C6 N2 1.405(8) . ?
C6 H6 0.95 . ?
C7 N1 1.335(8) . ?
C7 N2 1.352(8) . ?
C7 C8 1.493(12) . ?
C7 C8' 1.495(14) . ?
C8 C9 1.527(15) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.489(17) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.56(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.528(15) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.478(17) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.60(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.528(18) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.549(18) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.52(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.530(19) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C8' C9' 1.53(2) . ?
C8' H8C 0.99 . ?
C8' H8D 0.99 . ?
C9' C10' 1.48(2) . ?
C9' H9C 0.99 . ?
C9' H9D 0.99 . ?
C10' C11' 1.56(2) . ?
C10' H10C 0.99 . ?
C10' H10D 0.99 . ?
C11' C12' 1.513(19) . ?
C11' H11C 0.99 . ?
C11' H11D 0.99 . ?
C12' C13' 1.48(2) . ?
C12' H12C 0.99 . ?
C12' H12D 0.99 . ?
C13' C14' 1.62(3) . ?
C13' H13C 0.99 . ?
C13' H13D 0.99 . ?
C14' C15' 1.55(2) . ?
C14' H14C 0.99 . ?
C14' H14D 0.99 . ?
C15' C16' 1.58(2) . ?
C15' H15C 0.99 . ?
C15' H15D 0.99 . ?
C16' C17' 1.51(3) . ?
C16' H16C 0.99 . ?
C16' H16D 0.99 . ?
C17' C18' 1.51(2) . ?
C17' H17C 0.99 . ?
C17' H17D 0.99 . ?
C18' H18D 0.98 . ?
C18' H18E 0.98 . ?
C18' H18F 0.98 . ?
N1 Cu1 1.967(6) . ?
O1 Cu1 1.9087(7) . ?
O1 Cu1 1.9087(7) 2_655 ?
O1 Cu1 1.9087(7) 7 ?
O1 Cu1 1.9087(7) 8_545 ?
Cl1 Cu1 2.407(3) 2_655 ?
Cl1 Cu1 2.407(3) . ?
Cl2 Cu1 2.3744(18) . ?
Cl2 Cu1 2.4241(18) 7 ?

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 C1 C2 108.6(6) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
N2 C2 C1 105.4(6) . . ?
N2 C2 C3 117.5(7) . . ?
C1 C2 C3 137.1(7) . . ?
F1 C3 C4 121.9(8) . . ?
F1 C3 C2 116.4(7) . . ?
C4 C3 C2 121.7(8) . . ?
C3 C4 C5 118.4(8) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 122.4(7) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 N2 118.4(7) . . ?
C5 C6 H6 120.8 . . ?
N2 C6 H6 120.8 . . ?
N1 C7 N2 108.8(6) . . ?
N1 C7 C8 130(3) . . ?
N2 C7 C8 121(3) . . ?
N1 C7 C8' 126(4) . . ?
N2 C7 C8' 125(4) . . ?
C7 C8 C9 116.9(18) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C8 110.7(16) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 114.0(18) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 115.8(14) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C11 112.1(14) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 116.2(16) . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13B 108.2 . . ?
C14 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 C13 114.0(16) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 116.2(17) . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C15 110.7(18) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 114(2) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C8' C9' 110(3) . . ?
C7 C8' H8C 109.6 . . ?
C9' C8' H8C 109.6 . . ?
C7 C8' H8D 109.6 . . ?
C9' C8' H8D 109.6 . . ?
H8C C8' H8D 108.2 . . ?
C10' C9' C8' 113(2) . . ?
C10' C9' H9C 109 . . ?
C8' C9' H9C 109 . . ?
C10' C9' H9D 109 . . ?
C8' C9' H9D 109 . . ?
H9C C9' H9D 107.8 . . ?
C9' C10' C11' 114(2) . . ?
C9' C10' H10C 108.8 . . ?
C11' C10' H10C 108.8 . . ?
C9' C10' H10D 108.8 . . ?
C11' C10' H10D 108.8 . . ?
H10C C10' H10D 107.7 . . ?
C12' C11' C10' 115(2) . . ?
C12' C11' H11C 108.6 . . ?
C10' C11' H11C 108.6 . . ?
C12' C11' H11D 108.6 . . ?
C10' C11' H11D 108.6 . . ?
H11C C11' H11D 107.6 . . ?
C13' C12' C11' 118(2) . . ?
C13' C12' H12C 107.8 . . ?
C11' C12' H12C 107.8 . . ?
C13' C12' H12D 107.8 . . ?
C11' C12' H12D 107.8 . . ?
H12C C12' H12D 107.1 . . ?
C12' C13' C14' 112(2) . . ?
C12' C13' H13C 109.2 . . ?
C14' C13' H13C 109.2 . . ?
C12' C13' H13D 109.2 . . ?
C14' C13' H13D 109.2 . . ?
H13C C13' H13D 107.9 . . ?
C15' C14' C13' 109(2) . . ?
C15' C14' H14C 110 . . ?
C13' C14' H14C 110 . . ?
C15' C14' H14D 110 . . ?
C13' C14' H14D 110 . . ?
H14C C14' H14D 108.4 . . ?
C14' C15' C16' 113(2) . . ?
C14' C15' H15C 108.9 . . ?
C16' C15' H15C 108.9 . . ?
C14' C15' H15D 108.9 . . ?
C16' C15' H15D 108.9 . . ?
H15C C15' H15D 107.8 . . ?
C17' C16' C15' 102(2) . . ?
C17' C16' H16C 111.3 . . ?
C15' C16' H16C 111.3 . . ?
C17' C16' H16D 111.3 . . ?
C15' C16' H16D 111.3 . . ?
H16C C16' H16D 109.2 . . ?
C18' C17' C16' 116(3) . . ?
C18' C17' H17C 108.4 . . ?
C16' C17' H17C 108.4 . . ?
C18' C17' H17D 108.4 . . ?
C16' C17' H17D 108.4 . . ?
H17C C17' H17D 107.4 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C7 N1 C1 108.6(6) . . ?
C7 N1 Cu1 126.3(5) . . ?
C1 N1 Cu1 124.8(5) . . ?
C7 N2 C2 108.6(5) . . ?
C7 N2 C6 129.8(6) . . ?
C2 N2 C6 121.6(6) . . ?
Cu1 O1 Cu1 110.57(5) . 2_655 ?
Cu1 O1 Cu1 108.92(2) . 7 ?
Cu1 O1 Cu1 108.93(2) 2_655 7 ?
Cu1 O1 Cu1 108.93(2) . 8_545 ?
Cu1 O1 Cu1 108.93(2) 2_655 8_545 ?
Cu1 O1 Cu1 110.57(5) 7 8_545 ?
Cu1 Cl1 Cu1 81.37(12) 2_655 . ?
Cu1 Cl2 Cu1 80.68(6) . 7 ?
O1 Cu1 N1 177.36(17) . . ?
O1 Cu1 Cl2 85.75(5) . . ?
N1 Cu1 Cl2 94.50(15) . . ?
O1 Cu1 Cl1 84.03(6) . . ?
N1 Cu1 Cl1 97.99(18) . . ?
Cl2 Cu1 Cl1 123.60(6) . . ?
O1 Cu1 Cl2 84.36(5) . 8_545 ?
N1 Cu1 Cl2 93.26(16) . 8_545 ?
Cl2 Cu1 Cl2 119.85(4) . 8_545 ?
Cl1 Cu1 Cl2 114.04(6) . 8_545 ?

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2077018'
loop_
_audit_author_name
_audit_author_address
'Sonia Mallet-Ladeira'
;CNRS
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'C10 H8 F N3'
_chemical_formula_sum            'C10 H8 F N3'
_chemical_formula_weight         189.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'I b a m'
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_Int_Tables_number      72
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   15.8734(6)
_cell_length_b                   17.3509(7)
_cell_length_c                   6.6216(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1823.71(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      34.97

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_T_max  0.7469

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_number            32011
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.026
_diffrn_reflns_theta_max         34.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_Friedel_coverage         0
_reflns_number_total             2099
_reflns_number_gt                1819
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+0.3294P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2099
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.90580(7) 0.43618(6) 0.5 0.0391(2) Uani 1 2 d S T P . .
C2 C 0.81053(6) 0.42887(5) 0.5 0.0336(2) Uani 1 2 d S T P . .
H2A H 0.787837 0.455353 0.620747 0.04 Uiso 0.5 1 calc R U P . .
H2B H 0.787837 0.455353 0.379253 0.04 Uiso 0.5 1 calc R U P . .
C3 C 0.78074(5) 0.34786(4) 0.5 0.02325(15) Uani 1 2 d S T P . .
C4 C 0.62617(6) 0.37753(6) 0.5 0.03142(19) Uani 1 2 d S T P . .
H4 H 0.632563 0.431968 0.5 0.038 Uiso 1 2 calc R U P . .
C5 C 0.54848(6) 0.34482(7) 0.5 0.0371(2) Uani 1 2 d S T P . .
H5 H 0.500056 0.376994 0.5 0.044 Uiso 1 2 calc R U P . .
C6 C 0.53798(6) 0.26305(7) 0.5 0.0367(2) Uani 1 2 d S T P . .
H6 H 0.483359 0.24066 0.5 0.044 Uiso 1 2 calc R U P . .
C7 C 0.60766(6) 0.21836(6) 0.5 0.02986(18) Uani 1 2 d S T P . .
C8 C 0.68958(5) 0.25003(5) 0.5 0.02305(15) Uani 1 2 d S T P . .
C9 C 0.77194(5) 0.22345(5) 0.5 0.02289(15) Uani 1 2 d S T P . .
C10 C 0.80051(6) 0.14617(5) 0.5 0.02821(17) Uani 1 2 d S T P . .
N1 N 0.82721(4) 0.28501(4) 0.5 0.02336(15) Uani 1 2 d S T P . .
N2 N 0.69581(4) 0.32954(4) 0.5 0.02344(15) Uani 1 2 d S T P . .
N3 N 0.82499(6) 0.08353(5) 0.5 0.0417(2) Uani 1 2 d S T P . .
F1 F 0.60360(5) 0.14077(4) 0.5 0.04310(19) Uani 1 2 d S T P . .
H1A H 0.9230(10) 0.4904(10) 0.5 0.046(4) Uiso 1 2 d S . P . .
H1B H 0.9313(8) 0.4088(7) 0.382(2) 0.062(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5175(14) . ?
C1 H1A 0.979(17) . ?
C1 H1B 0.998(13) . ?
C1 H1B 0.998(13) 10_556 ?
C2 C3 1.4831(12) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 N1 1.3165(10) . ?
C3 N2 1.3851(10) . ?
C4 C5 1.3575(13) . ?
C4 N2 1.3841(11) . ?
C4 H4 0.95 . ?
C5 C6 1.4285(17) . ?
C5 H5 0.95 . ?
C6 C7 1.3508(14) . ?
C6 H6 0.95 . ?
C7 F1 1.3479(11) . ?
C7 C8 1.4117(11) . ?
C8 N2 1.3831(11) . ?
C8 C9 1.3862(11) . ?
C9 N1 1.3822(10) . ?
C9 C10 1.4156(12) . ?
C10 N3 1.1542(12) . ?

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
C2 C1 H1A 111.0(10) . . ?
C2 C1 H1B 111.4(8) . . ?
H1A C1 H1B 110.1(9) . . ?
C2 C1 H1B 111.4(8) . 10_556 ?
H1A C1 H1B 110.1(9) . 10_556 ?
H1B C1 H1B 102.7(15) . 10_556 ?
C3 C2 C1 113.39(8) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 N2 110.81(7) . . ?
N1 C3 C2 127.33(7) . . ?
N2 C3 C2 121.86(7) . . ?
C5 C4 N2 118.29(10) . . ?
C5 C4 H4 120.9 . . ?
N2 C4 H4 120.9 . . ?
C4 C5 C6 121.42(9) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 118.33(8) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
F1 C7 C6 122.29(9) . . ?
F1 C7 C8 115.64(8) . . ?
C6 C7 C8 122.07(9) . . ?
N2 C8 C9 105.33(7) . . ?
N2 C8 C7 117.00(8) . . ?
C9 C8 C7 137.67(8) . . ?
N1 C9 C8 109.97(7) . . ?
N1 C9 C10 121.92(7) . . ?
C8 C9 C10 128.11(7) . . ?
N3 C10 C9 179.00(10) . . ?
C3 N1 C9 106.53(7) . . ?
C8 N2 C4 122.89(7) . . ?
C8 N2 C3 107.37(7) . . ?
C4 N2 C3 129.74(8) . . ?

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 C2 C3 N1 0 . . . . ?
C1 C2 C3 N2 180 . . . . ?
N2 C4 C5 C6 0 . . . . ?
C4 C5 C6 C7 0 . . . . ?
C5 C6 C7 F1 180 . . . . ?
C5 C6 C7 C8 0 . . . . ?
F1 C7 C8 N2 180 . . . . ?
C6 C7 C8 N2 0 . . . . ?
F1 C7 C8 C9 0 . . . . ?
C6 C7 C8 C9 180 . . . . ?
N2 C8 C9 N1 0 . . . . ?
C7 C8 C9 N1 180 . . . . ?
N2 C8 C9 C10 180 . . . . ?
C7 C8 C9 C10 0 . . . . ?
N2 C3 N1 C9 0 . . . . ?
C2 C3 N1 C9 180 . . . . ?
C8 C9 N1 C3 0 . . . . ?
C10 C9 N1 C3 180 . . . . ?
C9 C8 N2 C4 180 . . . . ?
C7 C8 N2 C4 0 . . . . ?
C9 C8 N2 C3 0 . . . . ?
C7 C8 N2 C3 180 . . . . ?
C5 C4 N2 C8 0 . . . . ?
C5 C4 N2 C3 180 . . . . ?
N1 C3 N2 C8 0 . . . . ?
C2 C3 N2 C8 180 . . . . ?
N1 C3 N2 C4 180 . . . . ?
C2 C3 N2 C4 0 . . . . ?

