# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1-2F
_database_code_depnum_ccdc_archive 'CCDC 2080771'
loop_
_audit_author_name
_audit_author_address
'Guo Peng'
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 Br4 Co F2 N2 O2'
_chemical_formula_sum            'C28 H18 Br4 Co F2 N2 O2'
_chemical_formula_weight         831.01

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   11.3655(7)
_cell_length_b                   4.4847(3)
_cell_length_c                   26.7643(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.607(6)
_cell_angle_gamma                90
_cell_volume                     1345.07(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3342
_cell_measurement_theta_min      2.7110
_cell_measurement_theta_max      28.3430

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_F_000             802
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    6.624
_shelx_estimated_absorpt_T_min   0.241
_shelx_estimated_absorpt_T_max   0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10563
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.695
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3100
_reflns_number_gt                2499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0147P)²+1.2619P] 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         3100
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0527
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.37997(2) -0.11583(7) 0.22046(2) 0.03298(9) Uani 1 1 d . . . . .
Br2 Br 0.33919(2) 0.09527(7) 0.01179(2) 0.03154(9) Uani 1 1 d . . . . .
C1 C 0.5478(2) 0.2361(6) 0.17826(9) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.4425(2) 0.0622(6) 0.16649(10) 0.0194(5) Uani 1 1 d . . . . .
C3 C 0.3830(2) 0.0210(6) 0.11834(10) 0.0209(6) Uani 1 1 d . . . . .
H3 H 0.3152 -0.0984 0.1124 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4245(2) 0.1588(6) 0.07828(10) 0.0207(6) Uani 1 1 d . . . . .
C5 C 0.5228(2) 0.3399(6) 0.08673(10) 0.0205(6) Uani 1 1 d . . . . .
H5 H 0.5485 0.4359 0.0597 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5853(2) 0.3812(6) 0.13651(9) 0.0172(5) Uani 1 1 d . . . . .
C7 C 0.6864(2) 0.5812(6) 0.14170(9) 0.0180(5) Uani 1 1 d . . . . .
H7 H 0.7007 0.6735 0.1122 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8569(2) 0.8556(6) 0.17592(10) 0.0206(5) Uani 1 1 d . . . . .
H8A H 0.9000 0.9114 0.2090 0.025 Uiso 1 1 calc R U . . .
H8B H 0.8223 1.0352 0.1594 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9433(2) 0.7235(6) 0.14494(10) 0.0188(5) Uani 1 1 d . . . . .
C10 C 0.9450(2) 0.8128(6) 0.09595(11) 0.0267(6) Uani 1 1 d . . . . .
C11 C 1.0257(3) 0.7036(7) 0.06674(12) 0.0380(8) Uani 1 1 d . . . . .
H11 H 1.0247 0.7702 0.0338 0.046 Uiso 1 1 calc R U . . .
C12 C 1.1073(3) 0.4933(7) 0.08826(13) 0.0393(8) Uani 1 1 d . . . . .
H12 H 1.1620 0.4154 0.0695 0.047 Uiso 1 1 calc R U . . .
C13 C 1.1085(3) 0.3975(7) 0.13723(13) 0.0334(7) Uani 1 1 d . . . . .
H13 H 1.1644 0.2572 0.1515 0.040 Uiso 1 1 calc R U . . .
C14 C 1.0268(2) 0.5096(6) 0.16520(11) 0.0243(6) Uani 1 1 d . . . . .
H14 H 1.0274 0.4413 0.1981 0.029 Uiso 1 1 calc R U . . .
Co1 Co 0.7500 0.46217(11) 0.2500 0.01855(12) Uani 1 2 d S T P . .
F1 F 0.86545(16) 1.0237(4) 0.07502(6) 0.0387(4) Uani 1 1 d . . . . .
N1 N 0.75930(17) 0.6462(4) 0.18261(8) 0.0165(4) Uani 1 1 d . . . . .
O1 O 0.60347(15) 0.2569(4) 0.22485(7) 0.0225(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.890(2) . ?
Br2 C4 1.901(3) . ?
C1 O1 1.304(3) . ?
C1 C6 1.419(3) . ?
C1 C2 1.419(4) . ?
C2 C3 1.364(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C5 C6 1.413(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(3) . ?
C7 N1 1.291(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.486(3) . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.374(4) . ?
C9 C14 1.393(4) . ?
C10 F1 1.362(3) . ?
C10 C11 1.390(4) . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
Co1 O1 1.9235(17) 2_655 ?
Co1 O1 1.9236(17) . ?
Co1 N1 2.002(2) 2_655 ?
Co1 N1 2.002(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 124.0(2) . . ?
O1 C1 C2 120.5(2) . . ?
C6 C1 C2 115.5(2) . . ?
C3 C2 C1 123.4(2) . . ?
C3 C2 Br1 118.33(19) . . ?
C1 C2 Br1 118.25(19) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 Br2 121.23(19) . . ?
C3 C4 Br2 118.07(19) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C7 116.0(2) . . ?
C1 C6 C7 123.2(2) . . ?
N1 C7 C6 127.5(2) . . ?
N1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
N1 C8 C9 112.7(2) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 117.1(2) . . ?
C10 C9 C8 121.6(2) . . ?
C14 C9 C8 121.3(2) . . ?
F1 C10 C9 118.8(2) . . ?
F1 C10 C11 117.9(3) . . ?
C9 C10 C11 123.3(3) . . ?
C12 C11 C10 117.8(3) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O1 Co1 O1 122.81(11) 2_655 . ?
O1 Co1 N1 93.15(8) 2_655 2_655 ?
O1 Co1 N1 109.86(8) . 2_655 ?
O1 Co1 N1 109.86(8) 2_655 . ?
O1 Co1 N1 93.15(8) . . ?
N1 Co1 N1 131.31(12) 2_655 . ?
C7 N1 C8 115.2(2) . . ?
C7 N1 Co1 123.23(17) . . ?
C8 N1 Co1 121.44(16) . . ?
C1 O1 Co1 128.49(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.1(2) . . . . ?
C6 C1 C2 C3 3.3(4) . . . . ?
O1 C1 C2 Br1 4.0(3) . . . . ?
C6 C1 C2 Br1 -175.60(17) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
Br1 C2 C3 C4 177.54(19) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C2 C3 C4 Br2 179.94(19) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
Br2 C4 C5 C6 -179.44(19) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -178.8(2) . . . . ?
O1 C1 C6 C5 177.7(2) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
O1 C1 C6 C7 -3.3(4) . . . . ?
C2 C1 C6 C7 176.3(2) . . . . ?
C5 C6 C7 N1 -177.4(2) . . . . ?
C1 C6 C7 N1 3.6(4) . . . . ?
N1 C8 C9 C10 106.7(3) . . . . ?
N1 C8 C9 C14 -74.6(3) . . . . ?
C14 C9 C10 F1 -179.4(2) . . . . ?
C8 C9 C10 F1 -0.7(4) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 177.9(2) . . . . ?
F1 C10 C11 C12 179.1(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C12 C13 C14 C9 -1.0(4) . . . . ?
C10 C9 C14 C13 1.1(4) . . . . ?
C8 C9 C14 C13 -177.6(2) . . . . ?
C6 C7 N1 C8 178.8(2) . . . . ?
C6 C7 N1 Co1 2.5(4) . . . . ?
C9 C8 N1 C7 -66.3(3) . . . . ?
C9 C8 N1 Co1 110.0(2) . . . . ?
C6 C1 O1 Co1 -3.3(4) . . . . ?
C2 C1 O1 Co1 177.11(17) . . . . ?

_refine_diff_density_max         0.568
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.087


####################################################################### 
# 
# 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_2-3F
_database_code_depnum_ccdc_archive 'CCDC 2080772'
loop_
_audit_author_name
_audit_author_address
'Guo Peng'
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 Br4 Co F2 N3 O2'
_chemical_formula_sum            'C30 H21 Br4 Co F2 N3 O2'
_chemical_formula_weight         872.07
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0772(15)
_cell_length_b                   20.240(4)
_cell_length_c                   18.530(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.889(2)
_cell_angle_gamma                90
_cell_volume                     3029.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.417
_shelx_estimated_absorpt_T_min   0.196
_exptl_absorpt_coefficient_mu    5.889
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14469
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.445
_diffrn_reflns_theta_min         1.490
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3688
_reflns_number_total             5484
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        APEX3
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C12(H12), C14(H14), C17(H17), C19(H19),
 C20(H20), C21(H21), C24(H24), C26(H26), C27(H27), C28(H28)
3.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.01270(7) 1.06598(3) 0.62215(3) 0.03050(17) Uani 1 1 d . . . . .
Br2 Br -0.00352(8) 1.19596(3) 0.89154(4) 0.0429(2) Uani 1 1 d . . . . .
Br3 Br 0.06179(7) 0.65604(3) 0.85828(3) 0.02859(17) Uani 1 1 d . . . . .
Br4 Br -0.14621(8) 0.54425(3) 0.59334(4) 0.04050(19) Uani 1 1 d . . . . .
C1 C 0.1008(6) 1.0024(3) 0.7554(3) 0.0201(13) Uani 1 1 d . . . . .
C2 C 0.0472(6) 1.0629(3) 0.7239(3) 0.0228(13) Uani 1 1 d . . . . .
C3 C 0.0199(6) 1.1195(3) 0.7623(3) 0.0269(14) Uani 1 1 d . . . . .
H3 H -0.013851 1.157946 0.738868 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0431(7) 1.1187(3) 0.8366(3) 0.0316(15) Uani 1 1 d . . . . .
C5 C 0.0942(7) 1.0617(3) 0.8713(3) 0.0290(14) Uani 1 1 d . . . . .
H5 H 0.109042 1.061749 0.921133 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1240(6) 1.0037(3) 0.8320(3) 0.0205(13) Uani 1 1 d . . . . .
C7 C 0.1696(6) 0.9454(3) 0.8734(3) 0.0231(13) Uani 1 1 d . . . . .
H7 H 0.171668 0.949733 0.923377 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0750(6) 0.7258(3) 0.7247(3) 0.0186(12) Uani 1 1 d . . . . .
C9 C 0.0303(6) 0.6653(3) 0.7570(3) 0.0208(13) Uani 1 1 d . . . . .
C10 C -0.0321(6) 0.6116(3) 0.7194(3) 0.0268(14) Uani 1 1 d . . . . .
H10 H -0.058307 0.572612 0.743223 0.032 Uiso 1 1 calc R U . . .
C11 C -0.0545(6) 0.6170(3) 0.6453(3) 0.0287(15) Uani 1 1 d . . . . .
C12 C -0.0125(6) 0.6733(3) 0.6095(3) 0.0256(14) Uani 1 1 d . . . . .
H12 H -0.027082 0.675942 0.559723 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0533(6) 0.7276(3) 0.6483(3) 0.0197(13) Uani 1 1 d . . . . .
C14 C 0.0978(6) 0.7850(3) 0.6054(3) 0.0249(14) Uani 1 1 d . . . . .
H14 H 0.077449 0.781610 0.556050 0.030 Uiso 1 1 calc R U . . .
C15 C 0.2466(6) 0.8367(3) 0.9028(3) 0.0207(13) Uani 1 1 d . . . . .
H15A H 0.185080 0.796895 0.891133 0.025 Uiso 1 1 calc R U . . .
H15B H 0.211705 0.851861 0.949864 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4301(6) 0.8209(3) 0.9059(3) 0.0195(13) Uani 1 1 d . . . . .
C17 C 0.5436(6) 0.8697(3) 0.9240(3) 0.0229(13) Uani 1 1 d . . . . .
H17 H 0.507622 0.912329 0.933943 0.027 Uiso 1 1 calc R U . . .
C18 C 0.7092(7) 0.8548(3) 0.9273(3) 0.0258(14) Uani 1 1 d . . . . .
C19 C 0.7696(7) 0.7927(3) 0.9143(3) 0.0292(15) Uani 1 1 d . . . . .
H19 H 0.882292 0.783611 0.917771 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6560(7) 0.7440(3) 0.8959(3) 0.0321(15) Uani 1 1 d . . . . .
H20 H 0.692965 0.701526 0.885718 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4881(6) 0.7578(3) 0.8923(3) 0.0247(14) Uani 1 1 d . . . . .
H21 H 0.413471 0.724349 0.880626 0.030 Uiso 1 1 calc R U . . .
C22 C 0.1944(6) 0.8907(3) 0.5712(3) 0.0221(13) Uani 1 1 d . . . . .
H22A H 0.133859 0.930729 0.582120 0.026 Uiso 1 1 calc R U . . .
H22B H 0.155754 0.874578 0.524564 0.026 Uiso 1 1 calc R U . . .
C23 C 0.3765(6) 0.9058(3) 0.5679(3) 0.0223(13) Uani 1 1 d . . . . .
C24 C 0.4845(7) 0.8577(3) 0.5410(3) 0.0222(13) Uani 1 1 d . . . . .
H24 H 0.444916 0.817470 0.523571 0.027 Uiso 1 1 calc R U . . .
C25 C 0.6530(7) 0.8724(3) 0.5412(3) 0.0274(14) Uani 1 1 d . . . . .
C26 C 0.7166(7) 0.9320(3) 0.5630(3) 0.0339(16) Uani 1 1 d . . . . .
H26 H 0.829462 0.940654 0.560664 0.041 Uiso 1 1 calc R U . . .
C27 C 0.6081(7) 0.9785(3) 0.5882(3) 0.0375(16) Uani 1 1 d . . . . .
H27 H 0.648456 1.019238 0.603574 0.045 Uiso 1 1 calc R U . . .
C28 C 0.4400(7) 0.9660(3) 0.5914(3) 0.0276(14) Uani 1 1 d . . . . .
H28 H 0.369112 0.998059 0.609290 0.033 Uiso 1 1 calc R U . . .
C29 C 0.6035(8) 0.8619(3) 0.7349(3) 0.0377(17) Uani 1 1 d . . . . .
C30 C 0.784(3) 0.876(2) 0.7386(15) 0.057(9) Uani 0.60(6) 1 d . . P A 1
H30A H 0.823103 0.885642 0.690989 0.086 Uiso 0.60(6) 1 calc R U P A 1
H30B H 0.841815 0.838437 0.757691 0.086 Uiso 0.60(6) 1 calc R U P A 1
H30C H 0.803804 0.913610 0.769302 0.086 Uiso 0.60(6) 1 calc R U P A 1
C30A C 0.780(4) 0.842(2) 0.728(2) 0.047(9) Uani 0.40(6) 1 d . . P A 2
H30D H 0.830948 0.867472 0.691165 0.071 Uiso 0.40(6) 1 calc R U P A 2
H30E H 0.785713 0.795836 0.716279 0.071 Uiso 0.40(6) 1 calc R U P A 2
H30F H 0.837112 0.849438 0.773438 0.071 Uiso 0.40(6) 1 calc R U P A 2
Co1 Co 0.20985(8) 0.86270(3) 0.73683(4) 0.01755(18) Uani 1 1 d . . . . .
F1 F 0.8195(4) 0.90397(16) 0.94589(18) 0.0390(9) Uani 1 1 d . . . . .
F2 F 0.7572(4) 0.82438(17) 0.51566(19) 0.0452(10) Uani 1 1 d . . . . .
N1 N 0.2074(5) 0.8885(2) 0.8480(2) 0.0191(10) Uani 1 1 d . . . . .
N2 N 0.1622(5) 0.8402(2) 0.6272(2) 0.0180(10) Uani 1 1 d . . . . .
N3 N 0.4632(5) 0.8619(2) 0.7338(2) 0.0253(11) Uani 1 1 d . . . . .
O1 O 0.1207(4) 0.95050(17) 0.71492(19) 0.0225(9) Uani 1 1 d . . . . .
O2 O 0.1305(4) 0.77515(17) 0.76371(18) 0.0234(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.903(5) . ?
Br2 C4 1.908(6) . ?
Br3 C9 1.899(5) . ?
Br4 C11 1.903(6) . ?
C1 C2 1.421(7) . ?
C1 C6 1.429(7) . ?
C1 O1 1.301(6) . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(7) . ?
C4 C5 1.380(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(7) . ?
C6 C7 1.452(7) . ?
C7 H7 0.9300 . ?
C7 N1 1.283(6) . ?
C8 C9 1.413(7) . ?
C8 C13 1.424(7) . ?
C8 O2 1.308(6) . ?
C9 C10 1.383(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(7) . ?
C11 C12 1.365(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.412(7) . ?
C13 C14 1.455(7) . ?
C14 H14 0.9300 . ?
C14 N2 1.293(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.517(7) . ?
C15 N1 1.490(6) . ?
C16 C17 1.385(7) . ?
C16 C21 1.385(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(7) . ?
C18 C19 1.372(7) . ?
C18 F1 1.375(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.504(7) . ?
C22 N2 1.483(6) . ?
C23 C24 1.405(7) . ?
C23 C28 1.389(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.394(7) . ?
C25 C26 1.369(8) . ?
C25 F2 1.375(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.49(2) . ?
C29 C30A 1.49(3) . ?
C29 N3 1.133(7) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30A H30D 0.9600 . ?
C30A H30E 0.9600 . ?
C30A H30F 0.9600 . ?
Co1 N1 2.125(4) . ?
Co1 N2 2.111(4) . ?
Co1 N3 2.048(4) . ?
Co1 O1 1.958(3) . ?
Co1 O2 1.952(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
C2 C1 C6 115.2(5) . . ?
O1 C1 C2 119.9(5) . . ?
O1 C1 C6 124.9(5) . . ?
C1 C2 Br1 118.3(4) . . ?
C3 C2 Br1 117.7(4) . . ?
C3 C2 C1 124.0(5) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Br2 119.7(4) . . ?
C5 C4 Br2 119.8(5) . . ?
C5 C4 C3 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 122.6(5) . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 C7 116.7(5) . . ?
C6 C7 H7 116.8 . . ?
N1 C7 C6 126.5(5) . . ?
N1 C7 H7 116.8 . . ?
C9 C8 C13 114.5(5) . . ?
O2 C8 C9 121.0(5) . . ?
O2 C8 C13 124.5(5) . . ?
C8 C9 Br3 118.2(4) . . ?
C10 C9 Br3 117.6(4) . . ?
C10 C9 C8 124.2(5) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(5) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 Br4 118.9(4) . . ?
C12 C11 Br4 119.9(5) . . ?
C12 C11 C10 121.2(5) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C14 122.3(5) . . ?
C12 C13 C8 121.7(5) . . ?
C12 C13 C14 116.0(5) . . ?
C13 C14 H14 115.8 . . ?
N2 C14 C13 128.3(5) . . ?
N2 C14 H14 115.8 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N1 C15 H15A 109.3 . . ?
N1 C15 H15B 109.3 . . ?
N1 C15 C16 111.8(4) . . ?
C17 C16 C15 120.1(5) . . ?
C21 C16 C15 121.4(5) . . ?
C21 C16 C17 118.5(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 122.8(5) . . ?
C17 C18 F1 118.7(5) . . ?
C19 C18 F1 118.4(5) . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.4(5) . . ?
C20 C19 H19 121.3 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(5) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 120.7(5) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 C23 110.5(4) . . ?
C24 C23 C22 119.0(5) . . ?
C28 C23 C22 121.5(5) . . ?
C28 C23 C24 119.4(5) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 C23 117.5(5) . . ?
C25 C24 H24 121.2 . . ?
C26 C25 C24 123.5(5) . . ?
C26 C25 F2 119.7(5) . . ?
F2 C25 C24 116.8(5) . . ?
C25 C26 H26 121.1 . . ?
C25 C26 C27 117.7(5) . . ?
C27 C26 H26 121.1 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(6) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.3(5) . . ?
C27 C28 H28 119.8 . . ?
N3 C29 C30 169(2) . . ?
N3 C29 C30A 163.1(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C30A H30D 109.5 . . ?
C29 C30A H30E 109.5 . . ?
C29 C30A H30F 109.5 . . ?
H30D C30A H30E 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
N2 Co1 N1 168.85(15) . . ?
N3 Co1 N1 93.03(17) . . ?
N3 Co1 N2 98.02(17) . . ?
O1 Co1 N1 88.23(15) . . ?
O1 Co1 N2 86.29(16) . . ?
O1 Co1 N3 111.48(17) . . ?
O2 Co1 N1 88.15(15) . . ?
O2 Co1 N2 89.64(16) . . ?
O2 Co1 N3 109.39(17) . . ?
O2 Co1 O1 139.10(15) . . ?
C7 N1 C15 115.5(4) . . ?
C7 N1 Co1 125.6(4) . . ?
C15 N1 Co1 118.9(3) . . ?
C14 N2 C22 116.7(5) . . ?
C14 N2 Co1 123.6(4) . . ?
C22 N2 Co1 119.6(3) . . ?
C29 N3 Co1 177.3(5) . . ?
C1 O1 Co1 131.4(3) . . ?
C8 O2 Co1 131.5(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
Br1 C2 C3 C4 179.7(4) . . . . ?
Br2 C4 C5 C6 177.9(4) . . . . ?
Br3 C9 C10 C11 -179.4(4) . . . . ?
Br4 C11 C12 C13 179.1(4) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C6 C7 N1 6.0(8) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C2 C1 C6 C7 176.6(5) . . . . ?
C2 C1 O1 Co1 173.8(3) . . . . ?
C2 C3 C4 Br2 -177.3(4) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
C4 C5 C6 C7 -177.1(5) . . . . ?
C5 C6 C7 N1 -177.4(5) . . . . ?
C6 C1 C2 Br1 -180.0(3) . . . . ?
C6 C1 C2 C3 0.5(8) . . . . ?
C6 C1 O1 Co1 -8.2(7) . . . . ?
C6 C7 N1 C15 -178.9(5) . . . . ?
C6 C7 N1 Co1 -1.1(7) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C8 C13 C14 N2 0.9(8) . . . . ?
C9 C8 C13 C12 1.8(7) . . . . ?
C9 C8 C13 C14 -177.9(4) . . . . ?
C9 C8 O2 Co1 177.4(3) . . . . ?
C9 C10 C11 Br4 -178.2(4) . . . . ?
C9 C10 C11 C12 1.7(8) . . . . ?
C10 C11 C12 C13 -0.8(8) . . . . ?
C11 C12 C13 C8 -1.0(8) . . . . ?
C11 C12 C13 C14 178.7(5) . . . . ?
C12 C13 C14 N2 -178.8(5) . . . . ?
C13 C8 C9 Br3 177.7(3) . . . . ?
C13 C8 C9 C10 -0.9(7) . . . . ?
C13 C8 O2 Co1 -3.1(7) . . . . ?
C13 C14 N2 C22 -179.8(5) . . . . ?
C13 C14 N2 Co1 -3.1(7) . . . . ?
C15 C16 C17 C18 179.5(5) . . . . ?
C15 C16 C21 C20 -179.5(5) . . . . ?
C16 C15 N1 C7 -107.6(5) . . . . ?
C16 C15 N1 Co1 74.4(5) . . . . ?
C16 C17 C18 C19 -0.9(8) . . . . ?
C16 C17 C18 F1 -179.6(5) . . . . ?
C17 C16 C21 C20 -0.8(8) . . . . ?
C17 C18 C19 C20 1.2(9) . . . . ?
C18 C19 C20 C21 -1.3(8) . . . . ?
C19 C20 C21 C16 1.1(8) . . . . ?
C21 C16 C17 C18 0.7(8) . . . . ?
C22 C23 C24 C25 -177.6(5) . . . . ?
C22 C23 C28 C27 179.6(5) . . . . ?
C23 C22 N2 C14 -118.1(5) . . . . ?
C23 C22 N2 Co1 65.1(5) . . . . ?
C23 C24 C25 C26 -3.3(8) . . . . ?
C23 C24 C25 F2 179.1(4) . . . . ?
C24 C23 C28 C27 0.0(8) . . . . ?
C24 C25 C26 C27 2.5(9) . . . . ?
C25 C26 C27 C28 -0.4(9) . . . . ?
C26 C27 C28 C23 -0.8(9) . . . . ?
C28 C23 C24 C25 1.9(8) . . . . ?
F1 C18 C19 C20 179.9(5) . . . . ?
F2 C25 C26 C27 -179.9(5) . . . . ?
N1 C15 C16 C17 61.0(6) . . . . ?
N1 C15 C16 C21 -120.2(5) . . . . ?
N2 C22 C23 C24 69.8(6) . . . . ?
N2 C22 C23 C28 -109.7(6) . . . . ?
O1 C1 C2 Br1 -1.8(6) . . . . ?
O1 C1 C2 C3 178.7(5) . . . . ?
O1 C1 C6 C5 -177.9(5) . . . . ?
O1 C1 C6 C7 -1.5(8) . . . . ?
O2 C8 C9 Br3 -2.7(6) . . . . ?
O2 C8 C9 C10 178.7(5) . . . . ?
O2 C8 C13 C12 -177.8(5) . . . . ?
O2 C8 C13 C14 2.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3-4F
_database_code_depnum_ccdc_archive 'CCDC 2080773'
loop_
_audit_author_name
_audit_author_address
'Guo Peng'
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 Br4 Co F2 N2 O2'
_chemical_formula_sum            'C28 H18 Br4 Co F2 N2 O2'
_chemical_formula_weight         831.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   14.7016(7)
_cell_length_b                   9.6101(5)
_cell_length_c                   13.1023(7)
_cell_angle_alpha                90
_cell_angle_beta                 133.6210(10)
_cell_angle_gamma                90
_cell_volume                     1340.08(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4954
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_F_000             802
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    6.649
_shelx_estimated_absorpt_T_min   0.258
_shelx_estimated_absorpt_T_max   0.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5039
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8482
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.815
_diffrn_reflns_theta_max         26.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2697
_reflns_number_gt                2487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       APEX3
_computing_data_reduction        APEX3
_computing_structure_solution    'SHELXS-2013/1 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0294P)²+2.2799P] 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_abs_structure_details 
;
 Flack x determined using 1074 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45349(6) 0.13223(6) -0.38180(6) 0.02328(17) Uani 1 1 d . . . . .
Br2 Br 0.83711(6) 0.51101(7) -0.20332(7) 0.02516(17) Uani 1 1 d . . . . .
C1 C 0.5950(5) 0.2947(6) -0.1331(6) 0.0140(12) Uani 1 1 d . . . . .
C2 C 0.5815(6) 0.2615(7) -0.2480(6) 0.0175(13) Uani 1 1 d . . . . .
C3 C 0.6524(6) 0.3208(7) -0.2698(7) 0.0182(13) Uani 1 1 d . . . . .
H3 H 0.6407 0.2946 -0.3482 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7420(5) 0.4204(6) -0.1733(7) 0.0172(13) Uani 1 1 d . . . . .
C5 C 0.7629(6) 0.4550(7) -0.0575(7) 0.0190(13) Uani 1 1 d . . . . .
H5 H 0.8261 0.5209 0.0082 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6908(6) 0.3932(7) -0.0352(7) 0.0173(13) Uani 1 1 d . . . . .
C7 C 0.7268(5) 0.4276(7) 0.0963(6) 0.0176(13) Uani 1 1 d . . . . .
H7 H 0.8027 0.4785 0.1631 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7319(6) 0.4266(8) 0.2795(7) 0.0224(14) Uani 1 1 d . . . . .
H8A H 0.8117 0.4754 0.3265 0.027 Uiso 1 1 calc R U . . .
H8B H 0.7527 0.3376 0.3297 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6542(5) 0.5150(8) 0.2913(6) 0.0185(12) Uani 1 1 d . . . . .
C10 C 0.5843(6) 0.6272(9) 0.2017(7) 0.0299(15) Uani 1 1 d . . . . .
H10 H 0.5835 0.6478 0.1302 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5159(8) 0.7092(9) 0.2155(10) 0.040(2) Uani 1 1 d . . . . .
H11 H 0.4676 0.7854 0.1538 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5193(7) 0.6780(8) 0.3196(8) 0.0311(17) Uani 1 1 d . . . . .
C13 C 0.5889(6) 0.5704(8) 0.4128(7) 0.0267(16) Uani 1 1 d . . . . .
H13 H 0.5909 0.5526 0.4856 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6564(6) 0.4884(7) 0.3971(7) 0.0229(14) Uani 1 1 d . . . . .
H14 H 0.7049 0.4129 0.4599 0.027 Uiso 1 1 calc R U . . .
Co1 Co 0.5000 0.29684(13) 0.0000 0.0177(3) Uani 1 2 d S T P . .
F1 F 0.4518(5) 0.7565(6) 0.3346(6) 0.0575(15) Uani 1 1 d . . . . .
N1 N 0.6671(5) 0.3967(6) 0.1325(5) 0.0196(11) Uani 1 1 d . . . . .
O1 O 0.5228(4) 0.2350(5) -0.1217(5) 0.0186(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.899(6) . ?
Br2 C4 1.905(6) . ?
C1 O1 1.302(7) . ?
C1 C2 1.413(8) . ?
C1 C6 1.425(8) . ?
C2 C3 1.380(9) . ?
C3 C4 1.397(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(9) . ?
C5 C6 1.410(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.449(8) . ?
C7 N1 1.287(8) . ?
C7 H7 0.9500 . ?
C8 N1 1.473(8) . ?
C8 C9 1.514(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.387(9) . ?
C9 C10 1.390(10) . ?
C10 C11 1.384(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(11) . ?
C11 H11 0.9500 . ?
C12 F1 1.365(8) . ?
C12 C13 1.372(10) . ?
C13 C14 1.389(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Co1 O1 1.936(4) 2_655 ?
Co1 O1 1.936(4) . ?
Co1 N1 2.021(5) 2_655 ?
Co1 N1 2.021(5) . ?

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 C1 C2 119.7(5) . . ?
O1 C1 C6 124.5(5) . . ?
C2 C1 C6 115.8(5) . . ?
C3 C2 C1 123.8(6) . . ?
C3 C2 Br1 119.2(5) . . ?
C1 C2 Br1 116.9(4) . . ?
C2 C3 C4 118.1(6) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 Br2 118.9(5) . . ?
C3 C4 Br2 119.6(5) . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.7(6) . . ?
C5 C6 C7 116.1(6) . . ?
C1 C6 C7 123.0(5) . . ?
N1 C7 C6 127.0(6) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
N1 C8 C9 113.0(5) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 118.7(6) . . ?
C14 C9 C8 120.0(6) . . ?
C10 C9 C8 121.3(6) . . ?
C11 C10 C9 120.8(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 118.5(7) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 F1 119.6(7) . . ?
C11 C12 C13 123.1(7) . . ?
F1 C12 C13 117.3(7) . . ?
C12 C13 C14 117.8(6) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C9 C14 C13 121.1(6) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O1 Co1 O1 144.3(3) 2_655 . ?
O1 Co1 N1 93.10(19) 2_655 2_655 ?
O1 Co1 N1 103.72(19) . 2_655 ?
O1 Co1 N1 103.72(19) 2_655 . ?
O1 Co1 N1 93.10(19) . . ?
N1 Co1 N1 123.3(3) 2_655 . ?
C7 N1 C8 116.5(5) . . ?
C7 N1 Co1 121.8(4) . . ?
C8 N1 Co1 121.4(4) . . ?
C1 O1 Co1 125.3(4) . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.090





