# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_G129
_database_code_depnum_ccdc_archive 'CCDC 2180535'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL' 'CDIFX ISCR CNRS Univ Rennes, France'
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: ?                                                        #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H18 Br2 N2'
_chemical_formula_sum            'C18 H18 Br2 N2'
_chemical_formula_weight         422.16
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.2470(2)
_cell_length_b                   10.1878(5)
_cell_length_c                   19.0944(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.379(2)
_cell_angle_gamma                90
_cell_volume                     825.46(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.36
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0056765
_diffrn_orient_matrix_UB_21      0.2193078
_diffrn_orient_matrix_UB_31      -0.0860793
_diffrn_orient_matrix_UB_12      0.0855826
_diffrn_orient_matrix_UB_22      -0.0194652
_diffrn_orient_matrix_UB_32      -0.0439486
_diffrn_orient_matrix_UB_13      -0.0255623
_diffrn_orient_matrix_UB_23      -0.0140894
_diffrn_orient_matrix_UB_33      -0.0435379


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             420
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    4.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.162
_exptl_absorpt_correction_T_max  0.357

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

#..............................................................................#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0459
_diffrn_reflns_av_r_equivalents  0.0360
_diffrn_reflns_number            5458
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.925
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1907
_reflns_number_gt                1540
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+0.9133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1907
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.090

#------------------------------------------------------------------------------#
#               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 0.0000 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'
Br Br -0.2901 2.4595 '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
Br1 Br 0.00519(7) 0.63362(3) 0.92676(2) 0.02739(11) Uani 1 1 d . . . . .
C1 C 0.1383(6) 0.6504(3) 0.83342(12) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.0380(6) 0.5582(3) 0.78442(13) 0.0189(6) Uani 1 1 d . . . . .
H2 H -0.098225 0.489096 0.797280 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1373(6) 0.5671(3) 0.71629(13) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.069183 0.503513 0.682586 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3361(6) 0.6685(2) 0.69672(12) 0.0153(5) Uani 1 1 d . . . . .
C5 C 0.4287(6) 0.7615(3) 0.74733(13) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.560720 0.832107 0.734579 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3323(6) 0.7531(3) 0.81583(13) 0.0185(6) Uani 1 1 d . . . . .
H6 H 0.398258 0.816526 0.849826 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4494(6) 0.6727(3) 0.62369(13) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.5901(7) 0.7987(3) 0.59831(14) 0.0237(6) Uani 1 1 d . . . . .
H8A H 0.818428 0.797830 0.608170 0.036 Uiso 1 1 calc R U . . .
H8B H 0.496665 0.873066 0.622521 0.036 Uiso 1 1 calc R U . . .
H8C H 0.546987 0.807302 0.547698 0.036 Uiso 1 1 calc R U . . .
N9 N 0.4256(5) 0.5671(2) 0.58809(11) 0.0197(5) Uani 1 1 d . . . . .
C10 C 0.5380(7) 0.5655(3) 0.51654(13) 0.0227(6) Uani 1 1 d . . . . .
H10A H 0.768500 0.580411 0.517595 0.027 Uiso 1 1 calc R U . . .
H10B H 0.434880 0.636501 0.488636 0.027 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
Br1 C1 1.900(2) . ?
C1 C2 1.380(4) . ?
C1 C6 1.382(4) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(4) . ?
C4 C7 1.495(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N9 1.275(3) . ?
C7 C8 1.504(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 C10 1.466(3) . ?
C10 C10 1.505(5) 3_666 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 C6 121.4(2) . . ?
C2 C1 Br1 118.64(19) . . ?
C6 C1 Br1 119.98(19) . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 119.6(2) . . ?
C5 C4 C7 122.2(2) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N9 C7 C4 116.9(2) . . ?
N9 C7 C8 124.9(2) . . ?
C4 C7 C8 118.2(2) . . ?
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 . . ?
C7 N9 C10 119.0(2) . . ?
N9 C10 C10 109.2(3) . 3_666 ?
N9 C10 H10A 109.8 . . ?
C10 C10 H10A 109.8 3_666 . ?
N9 C10 H10B 109.8 . . ?
C10 C10 H10B 109.8 3_666 . ?
H10A C10 H10B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(4) . . . . ?
Br1 C1 C2 C3 -178.75(19) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C7 177.6(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C7 C4 C5 C6 -177.2(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
Br1 C1 C6 C5 179.15(19) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C3 C4 C7 N9 -17.4(3) . . . . ?
C5 C4 C7 N9 161.0(2) . . . . ?
C3 C4 C7 C8 164.3(2) . . . . ?
C5 C4 C7 C8 -17.3(4) . . . . ?
C4 C7 N9 C10 -179.0(2) . . . . ?
C8 C7 N9 C10 -0.8(4) . . . . ?
C7 N9 C10 C10 -175.6(3) . . . 3_666 ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_dv_ga_174
_database_code_depnum_ccdc_archive 'CCDC 2180539'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL' 'CDIFX ISCR CNRS Univ Rennes, France'
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H20 F6 N2 Ni O2 S2, C H2 Cl2'
_chemical_formula_sum            'C31 H22 Cl2 F6 N2 Ni O2 S2'
_chemical_formula_weight         762.23
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   18.4962(6)
_cell_length_b                   12.7149(6)
_cell_length_c                   14.2500(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.310(2)
_cell_angle_gamma                90
_cell_volume                     3232.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.27
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1544
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6192

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

_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_diffrn_reflns_av_uneti/neti     0.0084
_diffrn_reflns_av_r_equivalents  0.0406
_diffrn_reflns_number            142587
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3310
_reflns_number_gt                2715
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1012P)²+21.3528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3310
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2159
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.104

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 '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'
S S 0.1246 0.1234 '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
Ni1 Ni 0.500000 0.62774(6) 0.250000 0.0377(3) Uani 1 2 d S T P . .
S1 S 0.19963(9) 0.16480(14) -0.23175(11) 0.0708(5) Uani 1 1 d . . . . .
F1 F 0.4210(3) 0.8878(3) 0.0311(5) 0.1185(18) Uani 1 1 d . . . . .
F2 F 0.3155(3) 0.8188(3) -0.0334(3) 0.1047(16) Uani 1 1 d . . . . .
F3 F 0.3383(4) 0.8810(4) 0.1066(4) 0.127(2) Uani 1 1 d . . . . .
O1 O 0.45258(17) 0.7360(2) 0.1716(2) 0.0450(7) Uani 1 1 d . . . . .
N1 N 0.45661(17) 0.5221(2) 0.1638(2) 0.0336(7) Uani 1 1 d . . . . .
C15 C 0.2090(4) 0.0373(6) -0.2564(4) 0.0735(17) Uani 1 1 d . . . . .
H15 H 0.170634 -0.003047 -0.298465 0.088 Uiso 1 1 calc R U . . .
C14 C 0.2765(4) -0.0016(5) -0.2104(5) 0.0761(17) Uani 1 1 d . . . . .
H14 H 0.289400 -0.073145 -0.216366 0.091 Uiso 1 1 calc R U . . .
C13 C 0.3290(3) 0.0734(3) -0.1503(3) 0.0488(11) Uani 1 1 d . . . . .
H13 H 0.378892 0.059863 -0.113431 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2885(3) 0.1739(4) -0.1587(3) 0.0458(10) Uani 1 1 d . . . . .
C9 C 0.3170(2) 0.2695(3) -0.1043(3) 0.0397(9) Uani 1 1 d . . . . .
C8 C 0.3942(3) 0.2906(4) -0.0785(3) 0.0459(10) Uani 1 1 d . . . . .
H8 H 0.427012 0.246299 -0.101819 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4232(2) 0.3752(3) -0.0194(3) 0.0433(10) Uani 1 1 d . . . . .
H7 H 0.475581 0.388515 -0.002807 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2705(2) 0.3380(4) -0.0721(3) 0.0412(9) Uani 1 1 d . . . . .
H10 H 0.217908 0.326280 -0.090305 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2995(2) 0.4237(3) -0.0137(3) 0.0372(8) Uani 1 1 d . . . . .
H11 H 0.266533 0.470767 0.006235 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3765(2) 0.4409(3) 0.0159(3) 0.0362(8) Uani 1 1 d . . . . .
C4 C 0.4053(2) 0.5322(3) 0.0806(3) 0.0341(8) Uani 1 1 d . . . . .
C3 C 0.3753(2) 0.6321(3) 0.0464(3) 0.0417(9) Uani 1 1 d . . . . .
H3 H 0.335241 0.634926 -0.011163 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4010(2) 0.7234(3) 0.0917(3) 0.0411(9) Uani 1 1 d . . . . .
C1 C 0.3685(3) 0.8275(4) 0.0482(4) 0.0630(14) Uani 1 1 d . . . . .
C5 C 0.4896(2) 0.4181(3) 0.1956(3) 0.0445(10) Uani 1 1 d . . . . .
H5A H 0.534527 0.406139 0.171630 0.053 Uiso 1 1 calc R U . . .
H5B H 0.452812 0.361646 0.169841 0.053 Uiso 1 1 calc R U . . .
C16 C 0.500000 0.0478(12) 0.250000 0.144(6) Uani 1 2 d DS T P . .
H16A H 0.539333 0.001968 0.236492 0.173 Uiso 0.247(6) 1 calc R U P A 1
H16B H 0.460665 0.001972 0.263509 0.173 Uiso 0.247(6) 1 calc R U P A 1
H16D H 0.544360 0.001684 0.272144 0.173 Uiso 0.253(6) 1 calc R U P A 2
H16C H 0.455639 0.001686 0.227856 0.173 Uiso 0.253(6) 1 calc R U P A 2
Cl2 Cl 0.4598(9) 0.1264(9) 0.1444(8) 0.166(3) Uani 0.494(11) 1 d D . P A 1
Cl1 Cl 0.5101(9) 0.1185(8) 0.1523(9) 0.166(3) Uani 0.506(11) 1 d D . P A 2



#------------------------------------------------------------------------------#
#                              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
Ni1 O1 1.842(3) 2_655 ?
Ni1 O1 1.842(3) . ?
Ni1 N1 1.854(3) 2_655 ?
Ni1 N1 1.854(3) . ?
S1 C15 1.677(7) . ?
S1 C12 1.702(5) . ?
F1 C1 1.309(8) . ?
F2 C1 1.314(7) . ?
F3 C1 1.309(8) . ?
O1 C2 1.288(5) . ?
N1 C4 1.314(5) . ?
N1 C5 1.477(5) . ?
C15 C14 1.342(9) . ?
C15 H15 0.9500 . ?
C14 C13 1.465(7) . ?
C14 H14 0.9500 . ?
C13 C12 1.469(7) . ?
C13 H13 0.9500 . ?
C12 C9 1.463(6) . ?
C9 C10 1.385(6) . ?
C9 C8 1.403(6) . ?
C8 C7 1.384(6) . ?
C8 H8 0.9500 . ?
C7 C6 1.387(6) . ?
C7 H7 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C6 1.392(5) . ?
C11 H11 0.9500 . ?
C6 C4 1.492(5) . ?
C4 C3 1.420(5) . ?
C3 C2 1.352(6) . ?
C3 H3 0.9500 . ?
C2 C1 1.516(6) . ?
C5 C5 1.496(9) 2_655 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 Cl1 1.708(12) . ?
C16 Cl1 1.708(12) 2_655 ?
C16 Cl2 1.795(13) . ?
C16 Cl2 1.795(13) 2_655 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16D 0.9900 . ?
C16 H16C 0.9900 . ?

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 Ni1 O1 83.33(19) 2_655 . ?
O1 Ni1 N1 94.93(14) 2_655 2_655 ?
O1 Ni1 N1 175.25(14) . 2_655 ?
O1 Ni1 N1 175.25(14) 2_655 . ?
O1 Ni1 N1 94.93(14) . . ?
N1 Ni1 N1 87.15(19) 2_655 . ?
C15 S1 C12 93.3(3) . . ?
C2 O1 Ni1 124.5(3) . . ?
C4 N1 C5 120.4(3) . . ?
C4 N1 Ni1 127.6(3) . . ?
C5 N1 Ni1 112.0(2) . . ?
C14 C15 S1 112.9(5) . . ?
C14 C15 H15 123.6 . . ?
S1 C15 H15 123.6 . . ?
C15 C14 C13 115.6(6) . . ?
C15 C14 H14 122.2 . . ?
C13 C14 H14 122.2 . . ?
C14 C13 C12 105.9(5) . . ?
C14 C13 H13 127.0 . . ?
C12 C13 H13 127.0 . . ?
C9 C12 C13 125.1(4) . . ?
C9 C12 S1 122.3(4) . . ?
C13 C12 S1 112.3(3) . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 C12 122.0(4) . . ?
C8 C9 C12 119.8(4) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C7 C6 C11 118.8(4) . . ?
C7 C6 C4 122.5(4) . . ?
C11 C6 C4 118.7(4) . . ?
N1 C4 C3 121.4(4) . . ?
N1 C4 C6 122.4(3) . . ?
C3 C4 C6 116.1(3) . . ?
C2 C3 C4 123.2(4) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
O1 C2 C3 127.8(4) . . ?
O1 C2 C1 112.0(4) . . ?
C3 C2 C1 120.2(4) . . ?
F3 C1 F1 106.0(6) . . ?
F3 C1 F2 105.2(5) . . ?
F1 C1 F2 107.6(5) . . ?
F3 C1 C2 112.6(5) . . ?
F1 C1 C2 110.8(5) . . ?
F2 C1 C2 114.2(5) . . ?
N1 C5 C5 106.9(3) . 2_655 ?
N1 C5 H5A 110.3 . . ?
C5 C5 H5A 110.3 2_655 . ?
N1 C5 H5B 110.3 . . ?
C5 C5 H5B 110.3 2_655 . ?
H5A C5 H5B 108.6 . . ?
Cl1 C16 Cl1 116.5(12) . 2_655 ?
Cl2 C16 Cl2 112.4(12) . 2_655 ?
Cl2 C16 H16A 109.1 . . ?
Cl2 C16 H16A 109.1 2_655 . ?
Cl2 C16 H16B 109.1 . . ?
Cl2 C16 H16B 109.1 2_655 . ?
H16A C16 H16B 107.9 . . ?
Cl1 C16 H16D 108.2 . . ?
Cl1 C16 H16D 108.2 2_655 . ?
Cl1 C16 H16C 108.2 . . ?
Cl1 C16 H16C 108.2 2_655 . ?
H16D C16 H16C 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ni1 O1 C2 -177.1(4) 2_655 . . . ?
N1 Ni1 O1 C2 7.3(4) . . . . ?
O1 Ni1 N1 C4 -4.6(4) . . . . ?
N1 Ni1 N1 C4 171.1(4) 2_655 . . . ?
O1 Ni1 N1 C5 172.0(3) . . . . ?
N1 Ni1 N1 C5 -12.3(2) 2_655 . . . ?
C12 S1 C15 C14 1.3(5) . . . . ?
S1 C15 C14 C13 -1.4(8) . . . . ?
C15 C14 C13 C12 0.7(7) . . . . ?
C14 C13 C12 C9 174.7(4) . . . . ?
C14 C13 C12 S1 0.2(5) . . . . ?
C15 S1 C12 C9 -175.5(4) . . . . ?
C15 S1 C12 C13 -0.8(4) . . . . ?
C13 C12 C9 C10 -144.2(5) . . . . ?
S1 C12 C9 C10 29.7(6) . . . . ?
C13 C12 C9 C8 32.0(6) . . . . ?
S1 C12 C9 C8 -154.1(4) . . . . ?
C10 C9 C8 C7 2.4(6) . . . . ?
C12 C9 C8 C7 -173.9(4) . . . . ?
C9 C8 C7 C6 0.2(7) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C12 C9 C10 C11 174.5(4) . . . . ?
C9 C10 C11 C6 -1.6(6) . . . . ?
C8 C7 C6 C11 -3.6(6) . . . . ?
C8 C7 C6 C4 179.3(4) . . . . ?
C10 C11 C6 C7 4.3(6) . . . . ?
C10 C11 C6 C4 -178.5(3) . . . . ?
C5 N1 C4 C3 -177.1(4) . . . . ?
Ni1 N1 C4 C3 -0.7(6) . . . . ?
C5 N1 C4 C6 1.6(6) . . . . ?
Ni1 N1 C4 C6 178.0(3) . . . . ?
C7 C6 C4 N1 -56.7(6) . . . . ?
C11 C6 C4 N1 126.2(4) . . . . ?
C7 C6 C4 C3 122.0(4) . . . . ?
C11 C6 C4 C3 -55.1(5) . . . . ?
N1 C4 C3 C2 5.5(7) . . . . ?
C6 C4 C3 C2 -173.2(4) . . . . ?
Ni1 O1 C2 C3 -5.0(7) . . . . ?
Ni1 O1 C2 C1 175.3(3) . . . . ?
C4 C3 C2 O1 -2.6(8) . . . . ?
C4 C3 C2 C1 177.1(5) . . . . ?
O1 C2 C1 F3 -60.0(7) . . . . ?
C3 C2 C1 F3 120.2(6) . . . . ?
O1 C2 C1 F1 58.5(7) . . . . ?
C3 C2 C1 F1 -121.2(6) . . . . ?
O1 C2 C1 F2 -179.9(5) . . . . ?
C3 C2 C1 F2 0.4(8) . . . . ?
C4 N1 C5 C5 -150.0(4) . . . 2_655 ?
Ni1 N1 C5 C5 33.1(5) . . . 2_655 ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: tr.res
#...............................................................................


####################################################################### 
# 
# 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_G167_1
_database_code_depnum_ccdc_archive 'CCDC 2180538'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL' 'CDIFX ISCR CNRS Univ Rennes, France'
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 31 aout 2016                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H14 Br2 Cu F6 N2 O2'
_chemical_formula_sum            'C22 H14 Br2 Cu F6 N2 O2'
_chemical_formula_weight         675.71
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   19.941(3)
_cell_length_b                   9.7696(13)
_cell_length_c                   12.1230(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.103(5)
_cell_angle_gamma                90
_cell_volume                     2325.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7416
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0257639
_diffrn_orient_matrix_UB_21      -0.0434426
_diffrn_orient_matrix_UB_31      -0.0066111
_diffrn_orient_matrix_UB_12      0.0576893
_diffrn_orient_matrix_UB_22      0.0217798
_diffrn_orient_matrix_UB_32      0.0817001
_diffrn_orient_matrix_UB_13      -0.0464391
_diffrn_orient_matrix_UB_23      -0.0518691
_diffrn_orient_matrix_UB_33      0.0466185


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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1316
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    4.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_T_max  0.315

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0408
_diffrn_reflns_av_r_equivalents  0.0474
_diffrn_reflns_number            11309
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.329
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2672
_reflns_number_gt                2139
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014_4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  
'CRYSCALC (T. Roisnel, local program, ver. 2022)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+3.5266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.083

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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'

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
O1 O 0.45868(12) 0.3828(2) 0.65549(17) 0.0415(5) Uani 1 1 d . . . . .
C2 C 0.42348(15) 0.4044(3) 0.5579(2) 0.0322(6) Uani 1 1 d . . . . .
C3 C 0.39654(18) 0.2717(3) 0.5011(3) 0.0417(7) Uani 1 1 d . . . . .
F4 F 0.44509(13) 0.1794(2) 0.5002(2) 0.0716(7) Uani 1 1 d . . . . .
F5 F 0.34992(16) 0.2168(3) 0.5509(2) 0.0903(9) Uani 1 1 d . . . . .
F6 F 0.36838(14) 0.2878(2) 0.39378(17) 0.0737(7) Uani 1 1 d . . . . .
C7 C 0.40562(15) 0.5251(3) 0.5048(2) 0.0321(6) Uani 1 1 d . . . . .
H7 H 0.383419 0.521719 0.428861 0.039 Uiso 1 1 calc R U . . .
C8 C 0.41805(14) 0.6567(3) 0.5559(2) 0.0286(5) Uani 1 1 d . . . . .
N9 N 0.45610(12) 0.6721(2) 0.65487(18) 0.0306(5) Uani 1 1 d . . . . .
C10 C 0.46588(15) 0.8077(3) 0.7094(2) 0.0337(6) Uani 1 1 d . . . . .
H10A H 0.428255 0.826599 0.750769 0.040 Uiso 1 1 calc R U . . .
H10B H 0.465846 0.879955 0.652158 0.040 Uiso 1 1 calc R U . . .
C11 C 0.37965(14) 0.7719(3) 0.4920(2) 0.0289(6) Uani 1 1 d . . . . .
C12 C 0.38767(15) 0.8014(3) 0.3826(2) 0.0348(6) Uani 1 1 d . . . . .
H12 H 0.422374 0.756887 0.351412 0.042 Uiso 1 1 calc R U . . .
C13 C 0.34541(16) 0.8950(3) 0.3191(2) 0.0364(6) Uani 1 1 d . . . . .
H13 H 0.351325 0.916022 0.244865 0.044 Uiso 1 1 calc R U . . .
C14 C 0.29467(15) 0.9575(3) 0.3645(2) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.28635(15) 0.9319(3) 0.4734(2) 0.0352(6) Uani 1 1 d . . . . .
H15 H 0.251737 0.977206 0.504256 0.042 Uiso 1 1 calc R U . . .
C16 C 0.32939(15) 0.8390(3) 0.5368(2) 0.0340(6) Uani 1 1 d . . . . .
H16 H 0.324356 0.821016 0.611940 0.041 Uiso 1 1 calc R U . . .
Cu1 Cu 0.500000 0.52710(5) 0.750000 0.03021(14) Uani 1 2 d S T P . .
Br1 Br 0.23330(2) 1.07963(4) 0.27653(3) 0.05137(13) 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
O1 C2 1.283(3) . ?
O1 Cu1 1.910(2) . ?
C2 C7 1.360(4) . ?
C2 C3 1.521(4) . ?
C3 F5 1.308(4) . ?
C3 F4 1.324(4) . ?
C3 F6 1.333(4) . ?
C7 C8 1.430(4) . ?
C7 H7 0.9500 . ?
C8 N9 1.311(3) . ?
C8 C11 1.499(4) . ?
N9 C10 1.478(3) . ?
N9 Cu1 1.936(2) . ?
C10 C10 1.533(5) 2_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.385(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 Br1 1.897(3) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 O1 Cu1 122.71(18) . . ?
O1 C2 C7 129.4(3) . . ?
O1 C2 C3 111.7(2) . . ?
C7 C2 C3 118.8(3) . . ?
F5 C3 F4 107.7(3) . . ?
F5 C3 F6 106.6(3) . . ?
F4 C3 F6 104.8(3) . . ?
F5 C3 C2 111.4(3) . . ?
F4 C3 C2 112.5(3) . . ?
F6 C3 C2 113.3(3) . . ?
C2 C7 C8 124.3(3) . . ?
C2 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
N9 C8 C7 121.9(3) . . ?
N9 C8 C11 123.2(2) . . ?
C7 C8 C11 114.7(2) . . ?
C8 N9 C10 121.5(2) . . ?
C8 N9 Cu1 126.14(19) . . ?
C10 N9 Cu1 112.26(16) . . ?
N9 C10 C10 108.65(17) . 2_656 ?
N9 C10 H10A 110.0 . . ?
C10 C10 H10A 110.0 2_656 . ?
N9 C10 H10B 110.0 . . ?
C10 C10 H10B 110.0 2_656 . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 119.1(3) . . ?
C16 C11 C8 119.5(2) . . ?
C12 C11 C8 120.9(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 Br1 120.0(2) . . ?
C15 C14 Br1 118.5(2) . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 120.9(3) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O1 Cu1 O1 84.85(12) 2_656 . ?
O1 Cu1 N9 178.69(10) 2_656 . ?
O1 Cu1 N9 94.62(9) . . ?
O1 Cu1 N9 94.62(9) 2_656 2_656 ?
O1 Cu1 N9 178.69(10) . 2_656 ?
N9 Cu1 N9 85.95(13) . 2_656 ?

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
Cu1 O1 C2 C7 -3.5(5) . . . . ?
Cu1 O1 C2 C3 -179.9(2) . . . . ?
O1 C2 C3 F5 69.1(4) . . . . ?
C7 C2 C3 F5 -107.8(3) . . . . ?
O1 C2 C3 F4 -52.0(4) . . . . ?
C7 C2 C3 F4 131.1(3) . . . . ?
O1 C2 C3 F6 -170.7(3) . . . . ?
C7 C2 C3 F6 12.5(4) . . . . ?
O1 C2 C7 C8 -6.8(5) . . . . ?
C3 C2 C7 C8 169.4(3) . . . . ?
C2 C7 C8 N9 9.2(5) . . . . ?
C2 C7 C8 C11 -165.9(3) . . . . ?
C7 C8 N9 C10 -176.9(3) . . . . ?
C11 C8 N9 C10 -2.3(4) . . . . ?
C7 C8 N9 Cu1 -1.3(4) . . . . ?
C11 C8 N9 Cu1 173.34(19) . . . . ?
C8 N9 C10 C10 -154.0(3) . . . 2_656 ?
Cu1 N9 C10 C10 29.8(3) . . . 2_656 ?
N9 C8 C11 C16 -62.2(4) . . . . ?
C7 C8 C11 C16 112.8(3) . . . . ?
N9 C8 C11 C12 125.9(3) . . . . ?
C7 C8 C11 C12 -59.0(4) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
C8 C11 C12 C13 171.1(3) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C15 2.0(5) . . . . ?
C12 C13 C14 Br1 -177.0(2) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
Br1 C14 C15 C16 177.6(2) . . . . ?
C12 C11 C16 C15 1.5(4) . . . . ?
C8 C11 C16 C15 -170.5(3) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_G166
_database_code_depnum_ccdc_archive 'CCDC 2180536'
loop_
_audit_author_name
_audit_author_address
'Vincent DORCET'
;CDIFX ISCR CNRS Univ Rennes, France
France
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H16 Br2 F6 N2 O2'
_chemical_formula_sum            'C22 H16 Br2 F6 N2 O2'
_chemical_formula_weight         614.19
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9907(13)
_cell_length_b                   18.1315(19)
_cell_length_c                   10.3924(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.105(4)
_cell_angle_gamma                90
_cell_volume                     2313.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2490
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.93
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1208
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.651

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0297
_diffrn_reflns_av_uneti/neti     0.0661
_diffrn_reflns_number            8893
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.058
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             5250
_reflns_number_gt                3683
_reflns_threshold_expression     >2sigma(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.
;

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+2.3798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5250
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.293
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.098

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
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'
Br Br -0.2901 2.4595 '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 0.3588(3) 0.4321(3) 0.1335(4) 0.0359(10) Uani 1 1 d . . . . .
C2 C 0.4614(3) 0.4423(2) 0.2575(3) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.5606(3) 0.4211(2) 0.2446(3) 0.0225(8) Uani 1 1 d . . . . .
H3 H 0.561062 0.404454 0.158090 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6595(3) 0.42276(18) 0.3517(3) 0.0172(7) Uani 1 1 d . . . . .
C6 C 0.7580(2) 0.39718(19) 0.3207(3) 0.0165(7) Uani 1 1 d . . . . .
C7 C 0.7762(3) 0.42594(18) 0.2059(3) 0.0187(7) Uani 1 1 d . . . . .
H6 H 0.730443 0.464161 0.155763 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8599(3) 0.39979(19) 0.1635(3) 0.0201(7) Uani 1 1 d . . . . .
H7 H 0.871936 0.419744 0.085119 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9252(3) 0.34437(19) 0.2370(3) 0.0180(7) Uani 1 1 d . . . . .
C10 C 0.9101(3) 0.31508(19) 0.3524(3) 0.0207(7) Uani 1 1 d . . . . .
H9 H 0.957075 0.277440 0.402764 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8262(3) 0.34114(19) 0.3937(3) 0.0199(7) Uani 1 1 d . . . . .
H10 H 0.814592 0.320868 0.472126 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7626(2) 0.45363(19) 0.5938(3) 0.0179(7) Uani 1 1 d . . . . .
H11A H 0.821909 0.423613 0.580323 0.021 Uiso 1 1 calc R U . . .
H11B H 0.747031 0.433971 0.674390 0.021 Uiso 1 1 calc R U . . .
C25 C 0.8008(3) 0.53279(19) 0.6214(3) 0.0178(7) Uani 1 1 d . . . . .
H12A H 0.740363 0.563629 0.629677 0.021 Uiso 1 1 calc R U . . .
H12B H 0.861466 0.535406 0.708781 0.021 Uiso 1 1 calc R U . . .
C21 C 0.9455(3) 0.6134(2) 0.1647(4) 0.0258(8) Uani 1 1 d . . . . .
C22 C 0.9153(3) 0.59223(19) 0.2910(3) 0.0190(7) Uani 1 1 d . . . . .
C23 C 0.8191(3) 0.62253(19) 0.3031(3) 0.0217(8) Uani 1 1 d . . . . .
H15 H 0.777424 0.655304 0.234360 0.026 Uiso 1 1 calc R U . . .
C24 C 0.7826(3) 0.60634(19) 0.4115(3) 0.0185(7) Uani 1 1 d . . . . .
C26 C 0.6797(3) 0.64143(19) 0.4156(3) 0.0205(7) Uani 1 1 d . . . . .
C27 C 0.6801(3) 0.6892(2) 0.5194(4) 0.0303(9) Uani 1 1 d . . . . .
H18 H 0.746713 0.699888 0.589314 0.036 Uiso 1 1 calc R U . . .
C28 C 0.5844(3) 0.7217(2) 0.5224(4) 0.0337(9) Uani 1 1 d . . . . .
H19 H 0.584852 0.754770 0.593554 0.040 Uiso 1 1 calc R U . . .
C29 C 0.4891(3) 0.7054(2) 0.4212(4) 0.0285(9) Uani 1 1 d . . . . .
C30 C 0.4863(3) 0.6583(2) 0.3165(4) 0.0321(9) Uani 1 1 d . . . . .
H21 H 0.419321 0.647763 0.247127 0.039 Uiso 1 1 calc R U . . .
C31 C 0.5824(3) 0.6262(2) 0.3134(4) 0.0271(8) Uani 1 1 d . . . . .
H22 H 0.581498 0.593827 0.241213 0.033 Uiso 1 1 calc R U . . .
O1 O 0.44585(17) 0.46813(14) 0.3610(2) 0.0237(6) Uani 1 1 d . . . . .
O2 O 0.97923(18) 0.54951(14) 0.3714(2) 0.0231(5) Uani 1 1 d . . . . .
N1 N 0.6653(2) 0.44619(15) 0.4744(3) 0.0168(6) Uani 1 1 d . . . . .
H1 H 0.603274 0.458748 0.485306 0.020 Uiso 1 1 calc R U . . .
N2 N 0.8372(2) 0.56177(15) 0.5121(3) 0.0183(6) Uani 1 1 d . . . . .
H2 H 0.902518 0.548139 0.513109 0.022 Uiso 1 1 calc R U . . .
F1 F 0.2947(2) 0.49095(18) 0.1131(2) 0.0669(9) Uani 1 1 d . . . . .
F2 F 0.2998(2) 0.37561(18) 0.1541(2) 0.0643(9) Uani 1 1 d . . . . .
F3 F 0.37768(18) 0.41916(16) 0.0172(2) 0.0491(7) Uani 1 1 d . . . . .
F4 F 0.9434(2) 0.55463(13) 0.0871(2) 0.0532(7) Uani 1 1 d . . . . .
F5 F 1.04667(15) 0.64048(13) 0.2008(2) 0.0382(6) Uani 1 1 d . . . . .
F6 F 0.88053(16) 0.66385(13) 0.08547(19) 0.0328(5) Uani 1 1 d . . . . .
Br1 Br 1.03853(3) 0.30724(2) 0.17705(4) 0.02633(10) Uani 1 1 d . . . . .
Br2 Br 0.35762(3) 0.74937(2) 0.42653(5) 0.04535(14) 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 F1 1.327(5) . ?
C1 F3 1.331(4) . ?
C1 F2 1.337(5) . ?
C1 C2 1.533(5) . ?
C2 O1 1.248(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.398(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.323(4) . ?
C4 C6 1.492(4) . ?
C6 C7 1.392(4) . ?
C6 C11 1.397(5) . ?
C7 C8 1.383(4) . ?
C7 H6 0.9500 . ?
C8 C9 1.375(5) . ?
C8 H7 0.9500 . ?
C9 C10 1.383(4) . ?
C9 Br1 1.900(3) . ?
C10 C11 1.379(4) . ?
C10 H9 0.9500 . ?
C11 H10 0.9500 . ?
C5 N1 1.459(4) . ?
C5 C25 1.515(5) . ?
C5 H11A 0.9900 . ?
C5 H11B 0.9900 . ?
C25 N2 1.464(4) . ?
C25 H12A 0.9900 . ?
C25 H12B 0.9900 . ?
C21 F6 1.331(4) . ?
C21 F4 1.331(4) . ?
C21 F5 1.336(4) . ?
C21 C22 1.537(4) . ?
C22 O2 1.239(4) . ?
C22 C23 1.408(4) . ?
C23 C24 1.389(4) . ?
C23 H15 0.9500 . ?
C24 N2 1.328(4) . ?
C24 C26 1.493(4) . ?
C26 C27 1.382(5) . ?
C26 C31 1.387(5) . ?
C27 C28 1.386(5) . ?
C27 H18 0.9500 . ?
C28 C29 1.368(5) . ?
C28 H19 0.9500 . ?
C29 C30 1.375(5) . ?
C29 Br2 1.903(3) . ?
C30 C31 1.386(5) . ?
C30 H21 0.9500 . ?
C31 H22 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
F1 C1 F3 106.8(3) . . ?
F1 C1 F2 106.3(3) . . ?
F3 C1 F2 107.2(3) . . ?
F1 C1 C2 111.4(3) . . ?
F3 C1 C2 114.6(3) . . ?
F2 C1 C2 110.1(3) . . ?
O1 C2 C3 127.1(3) . . ?
O1 C2 C1 115.4(3) . . ?
C3 C2 C1 117.6(3) . . ?
C2 C3 C4 123.7(3) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
N1 C4 C3 121.5(3) . . ?
N1 C4 C6 121.7(3) . . ?
C3 C4 C6 116.8(3) . . ?
C7 C6 C11 118.9(3) . . ?
C7 C6 C4 117.8(3) . . ?
C11 C6 C4 123.0(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H6 119.5 . . ?
C6 C7 H6 119.5 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H7 120.7 . . ?
C7 C8 H7 120.7 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 Br1 118.7(2) . . ?
C10 C9 Br1 119.6(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H9 120.4 . . ?
C9 C10 H9 120.4 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H10 119.8 . . ?
C6 C11 H10 119.8 . . ?
N1 C5 C25 112.8(3) . . ?
N1 C5 H11A 109.0 . . ?
C25 C5 H11A 109.0 . . ?
N1 C5 H11B 109.0 . . ?
C25 C5 H11B 109.0 . . ?
H11A C5 H11B 107.8 . . ?
N2 C25 C5 111.2(3) . . ?
N2 C25 H12A 109.4 . . ?
C5 C25 H12A 109.4 . . ?
N2 C25 H12B 109.4 . . ?
C5 C25 H12B 109.4 . . ?
H12A C25 H12B 108.0 . . ?
F6 C21 F4 107.0(3) . . ?
F6 C21 F5 106.8(3) . . ?
F4 C21 F5 106.7(3) . . ?
F6 C21 C22 114.3(3) . . ?
F4 C21 C22 110.9(3) . . ?
F5 C21 C22 110.8(3) . . ?
O2 C22 C23 127.1(3) . . ?
O2 C22 C21 115.5(3) . . ?
C23 C22 C21 117.5(3) . . ?
C24 C23 C22 122.5(3) . . ?
C24 C23 H15 118.7 . . ?
C22 C23 H15 118.7 . . ?
N2 C24 C23 122.1(3) . . ?
N2 C24 C26 119.3(3) . . ?
C23 C24 C26 118.6(3) . . ?
C27 C26 C31 119.4(3) . . ?
C27 C26 C24 120.9(3) . . ?
C31 C26 C24 119.6(3) . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 H18 119.7 . . ?
C28 C27 H18 119.7 . . ?
C29 C28 C27 118.9(4) . . ?
C29 C28 H19 120.6 . . ?
C27 C28 H19 120.6 . . ?
C28 C29 C30 121.8(3) . . ?
C28 C29 Br2 118.8(3) . . ?
C30 C29 Br2 119.5(3) . . ?
C29 C30 C31 119.2(3) . . ?
C29 C30 H21 120.4 . . ?
C31 C30 H21 120.4 . . ?
C30 C31 C26 120.1(3) . . ?
C30 C31 H22 120.0 . . ?
C26 C31 H22 120.0 . . ?
C4 N1 C5 127.6(3) . . ?
C4 N1 H1 116.2 . . ?
C5 N1 H1 116.2 . . ?
C24 N2 C25 127.1(3) . . ?
C24 N2 H2 116.4 . . ?
C25 N2 H2 116.4 . . ?

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
F1 C1 C2 O1 45.5(5) . . . . ?
F3 C1 C2 O1 166.9(4) . . . . ?
F2 C1 C2 O1 -72.1(4) . . . . ?
F1 C1 C2 C3 -135.6(4) . . . . ?
F3 C1 C2 C3 -14.2(5) . . . . ?
F2 C1 C2 C3 106.8(4) . . . . ?
O1 C2 C3 C4 3.0(6) . . . . ?
C1 C2 C3 C4 -175.7(3) . . . . ?
C2 C3 C4 N1 -0.9(5) . . . . ?
C2 C3 C4 C6 179.3(3) . . . . ?
N1 C4 C6 C7 -130.6(3) . . . . ?
C3 C4 C6 C7 49.2(4) . . . . ?
N1 C4 C6 C11 55.7(5) . . . . ?
C3 C4 C6 C11 -124.5(4) . . . . ?
C11 C6 C7 C8 0.2(5) . . . . ?
C4 C6 C7 C8 -173.9(3) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C7 C8 C9 Br1 178.9(2) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
Br1 C9 C10 C11 -178.5(3) . . . . ?
C9 C10 C11 C6 -0.9(5) . . . . ?
C7 C6 C11 C10 0.2(5) . . . . ?
C4 C6 C11 C10 173.9(3) . . . . ?
N1 C5 C25 N2 -65.5(3) . . . . ?
F6 C21 C22 O2 -174.9(3) . . . . ?
F4 C21 C22 O2 64.0(4) . . . . ?
F5 C21 C22 O2 -54.2(4) . . . . ?
F6 C21 C22 C23 5.4(5) . . . . ?
F4 C21 C22 C23 -115.7(4) . . . . ?
F5 C21 C22 C23 126.1(3) . . . . ?
O2 C22 C23 C24 -0.8(6) . . . . ?
C21 C22 C23 C24 178.9(3) . . . . ?
C22 C23 C24 N2 0.8(5) . . . . ?
C22 C23 C24 C26 179.8(3) . . . . ?
N2 C24 C26 C27 62.2(5) . . . . ?
C23 C24 C26 C27 -116.8(4) . . . . ?
N2 C24 C26 C31 -118.2(4) . . . . ?
C23 C24 C26 C31 62.9(4) . . . . ?
C31 C26 C27 C28 0.2(5) . . . . ?
C24 C26 C27 C28 179.9(3) . . . . ?
C26 C27 C28 C29 0.4(6) . . . . ?
C27 C28 C29 C30 -0.6(6) . . . . ?
C27 C28 C29 Br2 179.4(3) . . . . ?
C28 C29 C30 C31 0.2(6) . . . . ?
Br2 C29 C30 C31 -179.8(3) . . . . ?
C29 C30 C31 C26 0.4(6) . . . . ?
C27 C26 C31 C30 -0.6(5) . . . . ?
C24 C26 C31 C30 179.7(3) . . . . ?
C3 C4 N1 C5 -177.5(3) . . . . ?
C6 C4 N1 C5 2.3(5) . . . . ?
C25 C5 N1 C4 102.8(4) . . . . ?
C23 C24 N2 C25 -171.2(3) . . . . ?
C26 C24 N2 C25 9.9(5) . . . . ?
C5 C25 N2 C24 101.8(4) . . . . ?

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
C5 H11A O2 0.99 2.51 3.254(4) 131.4 3_766 yes
C25 H12A O1 0.99 2.52 3.268(4) 132.3 3_666 yes
N1 H1 O1 0.88 2.04 2.734(3) 135.4 . yes
N1 H1 O1 0.88 2.32 3.007(3) 134.9 3_666 yes
N2 H2 O2 0.88 2.03 2.712(3) 133.4 . yes
N2 H2 O2 0.88 2.39 3.055(4) 132.2 3_766 yes
####################################################################### 
# 
# 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_G173
_database_code_depnum_ccdc_archive 'CCDC 2180537'
loop_
_audit_author_name
_audit_author_address
'Vincent DORCET'
;CDIFX ISCR CNRS Univ Rennes, France
France
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H14 Br2 F6 N2 Ni O2'
_chemical_formula_sum            'C22 H14 Br2 F6 N2 Ni O2'
_chemical_formula_weight         670.88
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   20.0985(14)
_cell_length_b                   9.6051(6)
_cell_length_c                   11.9138(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.023(2)
_cell_angle_gamma                90
_cell_volume                     2264.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3712
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0442195
_diffrn_orient_matrix_UB_21      -0.0047334
_diffrn_orient_matrix_UB_31      0.0239816
_diffrn_orient_matrix_UB_12      -0.0363739
_diffrn_orient_matrix_UB_22      0.0833963
_diffrn_orient_matrix_UB_32      -0.0506091
_diffrn_orient_matrix_UB_13      -0.0410736
_diffrn_orient_matrix_UB_23      -0.0510175
_diffrn_orient_matrix_UB_33      -0.0545487


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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1312
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    4.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_T_max  0.732

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

#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0475
_diffrn_reflns_av_r_equivalents  0.0458
_diffrn_reflns_number            8647
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_reflns_number_total             2579
_reflns_number_gt                2181
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014_4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1516P)²+41.0515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2579
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2525
_refine_ls_wR_factor_gt          0.2439
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.893
_refine_diff_density_min         -3.325
_refine_diff_density_rms         0.222

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 '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
C5 C 0.4655(4) 0.8090(8) 0.7112(6) 0.0191(15) Uani 1 1 d . . . . .
H1A H 0.429335 0.827389 0.755918 0.023 Uiso 1 1 calc R U . . .
H1B H 0.463778 0.881981 0.652008 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4183(4) 0.6542(8) 0.5577(6) 0.0141(14) Uani 1 1 d . . . . .
C3 C 0.4061(4) 0.5208(8) 0.5035(7) 0.0178(15) Uani 1 1 d . . . . .
H3 H 0.383687 0.516802 0.426488 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4255(4) 0.4004(8) 0.5591(7) 0.0176(15) Uani 1 1 d . . . . .
C1 C 0.4015(4) 0.2618(8) 0.5049(7) 0.0224(16) Uani 1 1 d . . . . .
C6 C 0.3790(4) 0.7715(8) 0.4951(6) 0.0169(15) Uani 1 1 d . . . . .
C7 C 0.3285(4) 0.8362(8) 0.5437(7) 0.0178(15) Uani 1 1 d . . . . .
H7 H 0.324263 0.815440 0.620074 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2845(4) 0.9303(8) 0.4813(7) 0.0194(16) Uani 1 1 d . . . . .
H8 H 0.249751 0.973236 0.513915 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2921(4) 0.9603(8) 0.3709(7) 0.0176(15) Uani 1 1 d . . . . .
C10 C 0.3421(4) 0.9012(8) 0.3212(7) 0.0199(15) Uani 1 1 d . . . . .
H10 H 0.346793 0.925343 0.245698 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3861(4) 0.8043(8) 0.3839(7) 0.0192(15) Uani 1 1 d . . . . .
H11 H 0.420626 0.761476 0.350650 0.023 Uiso 1 1 calc R U . . .
Br1 Br 0.22968(4) 1.08452(9) 0.28404(7) 0.0269(3) Uani 1 1 d . . . . .
F1 F 0.3603(4) 0.1989(6) 0.5641(6) 0.0443(16) Uani 1 1 d . . . . .
F2 F 0.4530(3) 0.1747(5) 0.5003(5) 0.0330(13) Uani 1 1 d . . . . .
F3 F 0.3684(3) 0.2759(6) 0.3991(5) 0.0328(13) Uani 1 1 d . . . . .
N1 N 0.4567(3) 0.6706(7) 0.6582(6) 0.0162(12) Uani 1 1 d . . . . .
O1 O 0.4603(3) 0.3841(6) 0.6607(5) 0.0210(12) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.52932(13) 0.750000 0.0148(4) Uani 1 2 d S T P . .



#------------------------------------------------------------------------------#
#                              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
C5 N1 1.469(9) . ?
C5 C5 1.526(15) 2_656 ?
C5 H1A 0.9900 . ?
C5 H1B 0.9900 . ?
C4 N1 1.316(10) . ?
C4 C3 1.437(10) . ?
C4 C6 1.499(10) . ?
C3 C2 1.356(11) . ?
C3 H3 0.9500 . ?
C2 O1 1.297(10) . ?
C2 C1 1.521(10) . ?
C1 F1 1.322(11) . ?
C1 F3 1.325(10) . ?
C1 F2 1.339(10) . ?
C6 C11 1.393(11) . ?
C6 C7 1.398(11) . ?
C7 C8 1.386(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(12) . ?
C9 Br1 1.901(8) . ?
C10 C11 1.406(11) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N1 Ni1 1.861(6) . ?
O1 Ni1 1.849(6) . ?

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 C5 C5 106.8(5) . 2_656 ?
N1 C5 H1A 110.4 . . ?
C5 C5 H1A 110.4 2_656 . ?
N1 C5 H1B 110.4 . . ?
C5 C5 H1B 110.4 2_656 . ?
H1A C5 H1B 108.6 . . ?
N1 C4 C3 122.9(7) . . ?
N1 C4 C6 122.6(7) . . ?
C3 C4 C6 114.4(6) . . ?
C2 C3 C4 121.9(7) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O1 C2 C3 128.4(7) . . ?
O1 C2 C1 111.7(7) . . ?
C3 C2 C1 119.7(7) . . ?
F1 C1 F3 107.3(7) . . ?
F1 C1 F2 107.2(7) . . ?
F3 C1 F2 106.8(7) . . ?
F1 C1 C2 110.7(7) . . ?
F3 C1 C2 112.6(7) . . ?
F2 C1 C2 112.0(7) . . ?
C11 C6 C7 119.7(7) . . ?
C11 C6 C4 120.7(7) . . ?
C7 C6 C4 119.1(7) . . ?
C8 C7 C6 120.6(7) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 118.7(8) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 122.3(7) . . ?
C10 C9 Br1 119.2(6) . . ?
C8 C9 Br1 118.5(6) . . ?
C9 C10 C11 119.0(7) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 119.6(8) . . ?
C6 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C4 N1 C5 120.4(6) . . ?
C4 N1 Ni1 126.0(5) . . ?
C5 N1 Ni1 113.5(5) . . ?
C2 O1 Ni1 123.7(5) . . ?
O1 Ni1 O1 82.1(4) . 2_656 ?
O1 Ni1 N1 177.5(3) . 2_656 ?
O1 Ni1 N1 95.8(3) 2_656 2_656 ?
O1 Ni1 N1 95.8(3) . . ?
O1 Ni1 N1 177.5(3) 2_656 . ?
N1 Ni1 N1 86.4(4) 2_656 . ?

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
N1 C4 C3 C2 9.5(12) . . . . ?
C6 C4 C3 C2 -165.4(8) . . . . ?
C4 C3 C2 O1 -5.2(14) . . . . ?
C4 C3 C2 C1 170.2(7) . . . . ?
O1 C2 C1 F1 62.8(10) . . . . ?
C3 C2 C1 F1 -113.3(9) . . . . ?
O1 C2 C1 F3 -177.1(7) . . . . ?
C3 C2 C1 F3 6.9(11) . . . . ?
O1 C2 C1 F2 -56.8(10) . . . . ?
C3 C2 C1 F2 127.1(8) . . . . ?
N1 C4 C6 C11 125.6(8) . . . . ?
C3 C4 C6 C11 -59.5(10) . . . . ?
N1 C4 C6 C7 -62.7(10) . . . . ?
C3 C4 C6 C7 112.2(8) . . . . ?
C11 C6 C7 C8 1.5(11) . . . . ?
C4 C6 C7 C8 -170.3(7) . . . . ?
C6 C7 C8 C9 -0.9(11) . . . . ?
C7 C8 C9 C10 -0.6(12) . . . . ?
C7 C8 C9 Br1 177.9(6) . . . . ?
C8 C9 C10 C11 1.4(12) . . . . ?
Br1 C9 C10 C11 -177.0(6) . . . . ?
C7 C6 C11 C10 -0.6(12) . . . . ?
C4 C6 C11 C10 171.1(7) . . . . ?
C9 C10 C11 C6 -0.8(12) . . . . ?
C3 C4 N1 C5 -177.9(7) . . . . ?
C6 C4 N1 C5 -3.3(11) . . . . ?
C3 C4 N1 Ni1 -1.7(11) . . . . ?
C6 C4 N1 Ni1 172.8(5) . . . . ?
C5 C5 N1 C4 -152.5(8) 2_656 . . . ?
C5 C5 N1 Ni1 30.9(9) 2_656 . . . ?
C3 C2 O1 Ni1 -6.6(12) . . . . ?
C1 C2 O1 Ni1 177.8(5) . . . . ?
C2 O1 Ni1 O1 -170.5(8) . . . 2_656 ?
C2 O1 Ni1 N1 10.8(7) . . . . ?
C4 N1 Ni1 O1 -6.9(7) . . . . ?
C5 N1 Ni1 O1 169.5(5) . . . . ?
C4 N1 Ni1 N1 171.9(8) . . . 2_656 ?
C5 N1 Ni1 N1 -11.8(4) . . . 2_656 ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


