# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_JMSV01sq
_database_code_depnum_ccdc_archive 'CCDC 1906397'
loop_
_audit_author_name
_audit_author_address
'Naytze Ortiz-Pastrana'
;Centro de Investigacion y de Estudios Avanzados del IPN
Mexico
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-04 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         'C26 H20 B2 F8 Fe N8'
_chemical_formula_sum            'C26 H20 B2 F8 Fe N8'
_chemical_formula_weight         673.97

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'
B B 0.0013 0.0007 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   16.375(3)
_cell_length_b                   12.327(3)
_cell_length_c                   17.399(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.25(3)
_cell_angle_gamma                90
_cell_volume                     3431.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8554
_cell_measurement_theta_min      2.3789
_cell_measurement_theta_max      20.9878

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent red'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   0.5768
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.511
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5768
_exptl_absorpt_correction_T_max  0.7455
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            55537
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.1307
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         26.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3536
_reflns_number_gt                2117
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²+0.6067P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3536
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Fe1 Fe 0.2500 0.36576(5) 0.5000 0.0515(3) Uani 1 2 d S T P . .
N1 N 0.33559(16) 0.4780(2) 0.50706(18) 0.0590(7) Uani 1 1 d . . . . .
N2 N 0.25230(16) 0.3676(2) 0.39222(16) 0.0565(7) Uani 1 1 d . . . . .
C2 C 0.3758(2) 0.5338(3) 0.5677(3) 0.0771(11) Uani 1 1 d . . . . .
H2 H 0.3655 0.5178 0.6170 0.092 Uiso 1 1 calc R U . . .
C4 C 0.4504(3) 0.6398(4) 0.4941(4) 0.1002(16) Uani 1 1 d . . . . .
H4 H 0.4891 0.6938 0.4906 0.120 Uiso 1 1 calc R U . . .
N4 N 0.12002(17) 0.1823(2) 0.48878(18) 0.0626(8) Uani 1 1 d . . . . .
H4A H 0.1192 0.1744 0.5377 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4331(3) 0.6159(3) 0.5622(4) 0.0952(15) Uani 1 1 d . . . . .
H3 H 0.4591 0.6536 0.6070 0.114 Uiso 1 1 calc R U . . .
N3 N 0.16729(15) 0.2547(2) 0.46137(16) 0.0549(7) Uani 1 1 d . . . . .
C6 C 0.4221(3) 0.6001(4) 0.3490(4) 0.1037(17) Uani 1 1 d . . . . .
H6 H 0.4604 0.6518 0.3402 0.124 Uiso 1 1 calc R U . . .
C5 C 0.4100(2) 0.5832(4) 0.4262(3) 0.0834(13) Uani 1 1 d . . . . .
C7 C 0.3787(4) 0.5420(4) 0.2875(3) 0.1064(16) Uani 1 1 d . . . . .
H7 H 0.3879 0.5555 0.2375 0.128 Uiso 1 1 calc R U . . .
C8 C 0.3208(3) 0.4632(4) 0.2967(3) 0.0871(13) Uani 1 1 d . . . . .
H8 H 0.2914 0.4247 0.2537 0.105 Uiso 1 1 calc R U . . .
C10 C 0.3522(2) 0.5024(3) 0.4355(2) 0.0648(10) Uani 1 1 d . . . . .
C11 C 0.2010(2) 0.3056(3) 0.3442(2) 0.0646(9) Uani 1 1 d . . . . .
H11 H 0.1974 0.3046 0.2901 0.077 Uiso 1 1 calc R U . . .
B11 B 0.4353(4) 0.1260(5) 0.3324(3) 0.0840(14) Uani 1 1 d . . . . .
F11 F 0.48467(19) 0.1038(3) 0.40518(18) 0.1364(12) Uani 1 1 d . . . . .
C12 C 0.1506(2) 0.2392(3) 0.3832(2) 0.0605(9) Uani 1 1 d . . . . .
F12 F 0.36258(19) 0.1673(3) 0.34426(15) 0.1386(13) Uani 1 1 d . . . . .
C13 C 0.0910(2) 0.1575(3) 0.3629(3) 0.0759(11) Uani 1 1 d . . . . .
H13 H 0.0678 0.1322 0.3126 0.091 Uiso 1 1 calc R U . . .
F13 F 0.4229(2) 0.0436(3) 0.2840(2) 0.1576(14) Uani 1 1 d . . . . .
C14 C 0.0741(2) 0.1233(3) 0.4307(3) 0.0744(11) Uani 1 1 d . . . . .
H14 H 0.0371 0.0683 0.4366 0.089 Uiso 1 1 calc R U . . .
F14 F 0.4726(3) 0.2031(3) 0.2966(2) 0.1678(15) Uani 1 1 d . . . . .
C9 C 0.3083(2) 0.4437(3) 0.3711(2) 0.0666(10) 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
Fe1 N2 1.884(3) 2_556 ?
Fe1 N2 1.884(3) . ?
Fe1 N3 1.942(3) . ?
Fe1 N3 1.942(3) 2_556 ?
Fe1 N1 1.955(3) 2_556 ?
Fe1 N1 1.955(3) . ?
N1 C2 1.313(5) . ?
N1 C10 1.363(4) . ?
N2 C11 1.299(4) . ?
N2 C9 1.414(4) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9300 . ?
C4 C3 1.308(7) . ?
C4 C5 1.412(7) . ?
C4 H4 0.9300 . ?
N4 N3 1.335(3) . ?
N4 C14 1.338(5) . ?
N4 H4A 0.8600 . ?
C3 H3 0.9300 . ?
N3 C12 1.342(4) . ?
C6 C7 1.356(7) . ?
C6 C5 1.414(7) . ?
C6 H6 0.9300 . ?
C5 C10 1.407(5) . ?
C7 C8 1.389(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(5) . ?
C8 H8 0.9300 . ?
C10 C9 1.397(5) . ?
C11 C12 1.432(5) . ?
C11 H11 0.9300 . ?
B11 F13 1.307(6) . ?
B11 F12 1.350(6) . ?
B11 F14 1.351(6) . ?
B11 F11 1.378(6) . ?
C12 C13 1.395(5) . ?
C13 C14 1.336(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Fe1 N2 178.65(17) 2_556 . ?
N2 Fe1 N3 101.13(11) 2_556 . ?
N2 Fe1 N3 79.84(12) . . ?
N2 Fe1 N3 79.84(12) 2_556 2_556 ?
N2 Fe1 N3 101.13(11) . 2_556 ?
N3 Fe1 N3 90.41(16) . 2_556 ?
N2 Fe1 N1 83.61(12) 2_556 2_556 ?
N2 Fe1 N1 95.43(12) . 2_556 ?
N3 Fe1 N1 92.23(11) . 2_556 ?
N3 Fe1 N1 163.43(12) 2_556 2_556 ?
N2 Fe1 N1 95.44(12) 2_556 . ?
N2 Fe1 N1 83.61(12) . . ?
N3 Fe1 N1 163.44(12) . . ?
N3 Fe1 N1 92.23(11) 2_556 . ?
N1 Fe1 N1 89.88(15) 2_556 . ?
C2 N1 C10 117.1(3) . . ?
C2 N1 Fe1 130.7(3) . . ?
C10 N1 Fe1 112.2(2) . . ?
C11 N2 C9 126.1(3) . . ?
C11 N2 Fe1 119.1(2) . . ?
C9 N2 Fe1 114.7(2) . . ?
N1 C2 C3 123.6(4) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N3 N4 C14 111.6(3) . . ?
N3 N4 H4A 124.2 . . ?
C14 N4 H4A 124.2 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N4 N3 C12 104.9(3) . . ?
N4 N3 Fe1 139.7(2) . . ?
C12 N3 Fe1 115.3(2) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C10 C5 C4 117.5(4) . . ?
C10 C5 C6 116.6(5) . . ?
C4 C5 C6 126.0(5) . . ?
C6 C7 C8 122.3(5) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 118.2(5) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
N1 C10 C9 116.8(3) . . ?
N1 C10 C5 122.0(4) . . ?
C9 C10 C5 121.2(4) . . ?
N2 C11 C12 112.9(3) . . ?
N2 C11 H11 123.5 . . ?
C12 C11 H11 123.5 . . ?
F13 B11 F12 111.7(5) . . ?
F13 B11 F14 105.9(5) . . ?
F12 B11 F14 107.8(4) . . ?
F13 B11 F11 114.7(4) . . ?
F12 B11 F11 107.4(4) . . ?
F14 B11 F11 109.2(5) . . ?
N3 C12 C13 109.9(3) . . ?
N3 C12 C11 112.6(3) . . ?
C13 C12 C11 137.3(4) . . ?
C14 C13 C12 105.5(4) . . ?
C14 C13 H13 127.2 . . ?
C12 C13 H13 127.2 . . ?
C13 C14 N4 107.9(3) . . ?
C13 C14 H14 126.0 . . ?
N4 C14 H14 126.0 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 N2 126.6(4) . . ?
C10 C9 N2 112.7(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
N3 Fe1 N2 C11 3.1(2) . . . . ?
N3 Fe1 N2 C11 91.5(3) 2_556 . . . ?
N1 Fe1 N2 C11 -88.2(3) 2_556 . . . ?
N1 Fe1 N2 C11 -177.4(3) . . . . ?
N3 Fe1 N2 C9 179.4(2) . . . . ?
N3 Fe1 N2 C9 -92.2(2) 2_556 . . . ?
N1 Fe1 N2 C9 88.1(2) 2_556 . . . ?
N1 Fe1 N2 C9 -1.2(2) . . . . ?
C10 N1 C2 C3 0.5(5) . . . . ?
Fe1 N1 C2 C3 -176.8(3) . . . . ?
C5 C4 C3 C2 0.9(7) . . . . ?
N1 C2 C3 C4 -1.1(7) . . . . ?
C14 N4 N3 C12 -0.7(4) . . . . ?
C14 N4 N3 Fe1 -178.4(3) . . . . ?
C3 C4 C5 C10 -0.1(7) . . . . ?
C3 C4 C5 C6 179.9(4) . . . . ?
C7 C6 C5 C10 1.1(7) . . . . ?
C7 C6 C5 C4 -178.9(5) . . . . ?
C5 C6 C7 C8 -0.4(8) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C2 N1 C10 C9 -179.1(3) . . . . ?
Fe1 N1 C10 C9 -1.3(4) . . . . ?
C2 N1 C10 C5 0.3(5) . . . . ?
Fe1 N1 C10 C5 178.1(3) . . . . ?
C4 C5 C10 N1 -0.5(6) . . . . ?
C6 C5 C10 N1 179.5(3) . . . . ?
C4 C5 C10 C9 178.9(4) . . . . ?
C6 C5 C10 C9 -1.1(6) . . . . ?
C9 N2 C11 C12 -178.3(3) . . . . ?
Fe1 N2 C11 C12 -2.5(4) . . . . ?
N4 N3 C12 C13 1.3(4) . . . . ?
Fe1 N3 C12 C13 179.7(2) . . . . ?
N4 N3 C12 C11 -175.7(3) . . . . ?
Fe1 N3 C12 C11 2.7(4) . . . . ?
N2 C11 C12 N3 -0.2(4) . . . . ?
N2 C11 C12 C13 -176.0(4) . . . . ?
N3 C12 C13 C14 -1.4(4) . . . . ?
C11 C12 C13 C14 174.5(4) . . . . ?
C12 C13 C14 N4 1.0(4) . . . . ?
N3 N4 C14 C13 -0.2(4) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C7 C8 C9 N2 179.8(4) . . . . ?
N1 C10 C9 C8 179.8(3) . . . . ?
C5 C10 C9 C8 0.3(6) . . . . ?
N1 C10 C9 N2 0.4(5) . . . . ?
C5 C10 C9 N2 -179.1(3) . . . . ?
C11 N2 C9 C8 -2.6(6) . . . . ?
Fe1 N2 C9 C8 -178.5(3) . . . . ?
C11 N2 C9 C10 176.7(3) . . . . ?
Fe1 N2 C9 C10 0.8(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
C2 H2 N2 0.93 2.65 3.116(5) 111.3 2_556
N4 H4A F11 0.86 2.31 2.936(4) 129.5 2_556
N4 H4A F12 0.86 2.01 2.864(4) 169.9 2_556
C3 H3 F14 0.93 2.53 3.434(6) 164.9 5_666
C11 H11 F12 0.93 2.36 3.240(4) 157.4 7
C14 H14 F11 0.93 2.31 3.148(5) 149.6 6

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.052



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/Diethylether'
####################################################################### 
# 
# 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_ICQ02
_database_code_depnum_ccdc_archive 'CCDC 1906398'
loop_
_audit_author_name
_audit_author_address
'Juan Olguin'
;Cinvestav
Mexico
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C60 H66 B4 Co2 F16 N16 O5'
_chemical_formula_sum            'C60 H66 B4 Co2 F16 N16 O5'
_chemical_formula_weight         1556.38

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.699(9)
_cell_length_b                   12.540(4)
_cell_length_c                   15.873(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.63(2)
_cell_angle_gamma                90
_cell_volume                     3754(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    166(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.44

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   0.6754
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.537
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      166(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_reflns_number            136569
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         28.907
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4894
_reflns_number_gt                3948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1076P)²+2.1227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4894
_refine_ls_number_parameters     279
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.058
_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
Co1 Co 0.500000 0.38494(3) 0.250000 0.03790(15) Uani 1 2 d S T P . .
F1 F 0.39986(12) 0.8865(2) 0.4378(2) 0.1180(10) Uani 1 1 d . . . . .
B1 B 0.33560(18) 0.8500(3) 0.4163(3) 0.0704(9) Uani 1 1 d . . . . .
N1 N 0.49112(9) 0.50085(14) 0.34273(13) 0.0456(4) Uani 1 1 d . . . . .
N2 N 0.44871(11) 0.56994(18) 0.35455(16) 0.0555(5) Uani 1 1 d . . . . .
H2 H 0.402740 0.574304 0.314672 0.067 Uiso 1 1 calc R U . . .
N3 N 0.60468(9) 0.39020(13) 0.36566(12) 0.0401(4) Uani 1 1 d . . . . .
C3 C 0.48324(17) 0.6310(2) 0.4326(2) 0.0630(7) Uani 1 1 d . . . . .
H3 H 0.463033 0.684481 0.453869 0.076 Uiso 1 1 calc R U . . .
C5 C 0.61935(17) 0.6307(2) 0.5602(2) 0.0665(7) Uani 1 1 d . . . . .
H5 H 0.621035 0.685266 0.602835 0.080 Uiso 1 1 calc R U . . .
N4 N 0.55253(9) 0.25864(14) 0.22004(12) 0.0421(4) Uani 1 1 d . . . . .
C4 C 0.55440(15) 0.60230(19) 0.47742(19) 0.0541(6) Uani 1 1 d . . . . .
C8 C 0.61794(11) 0.46771(17) 0.43590(14) 0.0436(4) Uani 1 1 d . . . . .
C7 C 0.68016(13) 0.4965(2) 0.51590(17) 0.0551(6) Uani 1 1 d . . . . .
H7 H 0.723278 0.462309 0.529927 0.066 Uiso 1 1 calc R U . . .
C6 C 0.67978(16) 0.5774(2) 0.57749(19) 0.0666(7) Uani 1 1 d . . . . .
H6 H 0.723266 0.595862 0.633339 0.080 Uiso 1 1 calc R U . . .
C9 C 0.55566(11) 0.52096(17) 0.41775(14) 0.0435(4) Uani 1 1 d . . . . .
C15 C 0.52304(13) 0.1890(2) 0.14841(18) 0.0533(5) Uani 1 1 d . . . . .
H15 H 0.474075 0.195802 0.102382 0.064 Uiso 1 1 calc R U . . .
C14 C 0.56116(18) 0.1063(2) 0.1382(2) 0.0686(8) Uani 1 1 d . . . . .
H14 H 0.538678 0.056607 0.086633 0.082 Uiso 1 1 calc R U . . .
C13 C 0.63203(18) 0.0977(2) 0.2042(2) 0.0705(8) Uani 1 1 d . . . . .
H13 H 0.659318 0.042037 0.198169 0.085 Uiso 1 1 calc R U . . .
C12 C 0.66358(14) 0.1698(2) 0.2791(2) 0.0594(6) Uani 1 1 d . . . . .
H12 H 0.712716 0.165376 0.324993 0.071 Uiso 1 1 calc R U . . .
C11 C 0.62194(12) 0.24863(17) 0.28559(15) 0.0433(4) Uani 1 1 d . . . . .
C10 C 0.64913(11) 0.32489(17) 0.36528(15) 0.0439(5) Uani 1 1 d . . . . .
H10 H 0.697589 0.325607 0.414333 0.053 Uiso 1 1 calc R U . . .
C20 C 0.2800(3) 0.6516(4) 0.1535(4) 0.1220(16) Uani 1 1 d . . . . .
H1A H 0.301286 0.658800 0.111909 0.183 Uiso 1 1 calc R U . . .
H1B H 0.289494 0.716107 0.192928 0.183 Uiso 1 1 calc R U . . .
H1C H 0.228629 0.641873 0.113121 0.183 Uiso 1 1 calc R U . . .
O1 O 0.30833(14) 0.5658(2) 0.2125(2) 0.1061(9) Uani 1 1 d D . . . .
H1 H 0.297(5) 0.493(2) 0.194(6) 0.28(5) Uiso 1 1 d D . . . .
F2A F 0.2815(3) 0.8891(4) 0.3348(5) 0.0807(16) Uani 0.626(12) 1 d . . P A 1
F3A F 0.3218(2) 0.8685(7) 0.4925(3) 0.122(3) Uani 0.626(12) 1 d . . P A 1
F4A F 0.3391(4) 0.7426(5) 0.4114(8) 0.147(3) Uani 0.626(12) 1 d . . P A 1
F2B F 0.3276(6) 0.7709(10) 0.4512(9) 0.137(6) Uani 0.374(12) 1 d . U P A 2
F3B F 0.3050(8) 0.9365(10) 0.4327(16) 0.182(7) Uani 0.374(12) 1 d . U P A 2
F4B F 0.2912(10) 0.8572(16) 0.3205(13) 0.193(8) Uani 0.374(12) 1 d . U P A 2
O30 O 0.500000 0.1039(11) 0.750000 0.145(4) Uani 0.5 2 d DS T P . .
C31 C 0.4483(7) 0.1767(12) 0.6936(12) 0.197(7) Uani 0.5 1 d D . P . .
H31A H 0.467429 0.231433 0.667763 0.236 Uiso 0.5 1 calc R U P . .
H31B H 0.429303 0.212475 0.731544 0.236 Uiso 0.5 1 calc R U P . .
C32 C 0.3931(9) 0.1133(10) 0.6148(11) 0.157(5) Uani 0.5 1 d D . P . .
H32A H 0.397673 0.038435 0.634810 0.236 Uiso 0.5 1 calc R U P . .
H32B H 0.398507 0.118928 0.557141 0.236 Uiso 0.5 1 calc R U P . .
H32C H 0.346331 0.140037 0.599610 0.236 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.100(2) . ?
Co1 N3 2.100(2) 2_655 ?
Co1 N4 2.1377(18) . ?
Co1 N4 2.1377(18) 2_655 ?
Co1 N1 2.1439(19) . ?
Co1 N1 2.1439(19) 2_655 ?
F1 B1 1.341(4) . ?
B1 F2B 1.190(8) . ?
B1 F2A 1.338(6) . ?
B1 F4B 1.342(17) . ?
B1 F4A 1.353(7) . ?
B1 F3B 1.362(11) . ?
B1 F3A 1.403(6) . ?
N1 C9 1.339(3) . ?
N1 N2 1.343(3) . ?
N2 C3 1.328(4) . ?
N2 H2 0.8800 . ?
N3 C10 1.267(3) . ?
N3 C8 1.398(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C5 C6 1.373(5) . ?
C5 C4 1.417(4) . ?
C5 H5 0.9500 . ?
N4 C15 1.322(3) . ?
N4 C11 1.348(3) . ?
C4 C9 1.401(3) . ?
C8 C7 1.368(3) . ?
C8 C9 1.404(3) . ?
C7 C6 1.412(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C15 C14 1.384(4) . ?
C15 H15 0.9500 . ?
C14 C13 1.371(5) . ?
C14 H14 0.9500 . ?
C13 C12 1.377(4) . ?
C13 H13 0.9500 . ?
C12 C11 1.377(3) . ?
C12 H12 0.9500 . ?
C11 C10 1.458(3) . ?
C10 H10 0.9500 . ?
C20 O1 1.358(6) . ?
C20 H1A 0.9800 . ?
C20 H1B 0.9800 . ?
C20 H1C 0.9800 . ?
O1 H1 0.956(10) . ?
O30 C31 1.378(9) 2_656 ?
O30 C31 1.378(9) . ?
C31 C32 1.466(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Co1 N3 176.40(9) . 2_655 ?
N3 Co1 N4 75.67(7) . . ?
N3 Co1 N4 107.10(7) 2_655 . ?
N3 Co1 N4 107.10(7) . 2_655 ?
N3 Co1 N4 75.67(7) 2_655 2_655 ?
N4 Co1 N4 84.39(10) . 2_655 ?
N3 Co1 N1 78.70(7) . . ?
N3 Co1 N1 98.82(7) 2_655 . ?
N4 Co1 N1 153.35(7) . . ?
N4 Co1 N1 96.36(7) 2_655 . ?
N3 Co1 N1 98.82(7) . 2_655 ?
N3 Co1 N1 78.70(7) 2_655 2_655 ?
N4 Co1 N1 96.36(7) . 2_655 ?
N4 Co1 N1 153.35(7) 2_655 2_655 ?
N1 Co1 N1 94.63(11) . 2_655 ?
F2B B1 F1 122.6(6) . . ?
F2A B1 F1 115.2(4) . . ?
F2B B1 F4B 113.3(10) . . ?
F1 B1 F4B 109.8(9) . . ?
F2A B1 F4A 110.9(6) . . ?
F1 B1 F4A 105.8(5) . . ?
F2B B1 F3B 112.2(9) . . ?
F1 B1 F3B 102.9(6) . . ?
F4B B1 F3B 91.0(10) . . ?
F2A B1 F3A 108.3(4) . . ?
F1 B1 F3A 111.3(4) . . ?
F4A B1 F3A 104.9(5) . . ?
C9 N1 N2 103.99(18) . . ?
C9 N1 Co1 109.19(14) . . ?
N2 N1 Co1 146.48(15) . . ?
C3 N2 N1 113.1(2) . . ?
C3 N2 H2 123.4 . . ?
N1 N2 H2 123.4 . . ?
C10 N3 C8 126.60(18) . . ?
C10 N3 Co1 118.18(14) . . ?
C8 N3 Co1 115.23(14) . . ?
N2 C3 C4 107.4(2) . . ?
N2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C15 N4 C11 118.91(19) . . ?
C15 N4 Co1 126.63(16) . . ?
C11 N4 Co1 114.36(13) . . ?
C3 C4 C9 103.3(2) . . ?
C3 C4 C5 138.8(2) . . ?
C9 C4 C5 117.8(3) . . ?
C7 C8 N3 130.1(2) . . ?
C7 C8 C9 118.3(2) . . ?
N3 C8 C9 111.69(18) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 122.9(2) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
N1 C9 C4 112.1(2) . . ?
N1 C9 C8 124.76(19) . . ?
C4 C9 C8 123.1(2) . . ?
N4 C15 C14 122.2(2) . . ?
N4 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C13 C14 C15 118.6(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N4 C11 C12 122.2(2) . . ?
N4 C11 C10 115.28(18) . . ?
C12 C11 C10 122.5(2) . . ?
N3 C10 C11 116.46(18) . . ?
N3 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
O1 C20 H1A 109.5 . . ?
O1 C20 H1B 109.5 . . ?
H1A C20 H1B 109.5 . . ?
O1 C20 H1C 109.5 . . ?
H1A C20 H1C 109.5 . . ?
H1B C20 H1C 109.5 . . ?
C20 O1 H1 126(6) . . ?
C31 O30 C31 97.1(16) 2_656 . ?
O30 C31 C32 104.7(12) . . ?
O30 C31 H31A 110.8 . . ?
C32 C31 H31A 110.8 . . ?
O30 C31 H31B 110.8 . . ?
C32 C31 H31B 110.8 . . ?
H31A C31 H31B 108.9 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 C3 -0.3(3) . . . . ?
Co1 N1 N2 C3 -172.0(2) . . . . ?
N1 N2 C3 C4 0.2(3) . . . . ?
N2 C3 C4 C9 -0.1(3) . . . . ?
N2 C3 C4 C5 -179.3(3) . . . . ?
C6 C5 C4 C3 179.3(3) . . . . ?
C6 C5 C4 C9 0.1(4) . . . . ?
C10 N3 C8 C7 4.1(4) . . . . ?
Co1 N3 C8 C7 -175.5(2) . . . . ?
C10 N3 C8 C9 -175.5(2) . . . . ?
Co1 N3 C8 C9 5.0(2) . . . . ?
N3 C8 C7 C6 -179.1(2) . . . . ?
C9 C8 C7 C6 0.4(4) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C8 C7 C6 C5 -0.9(4) . . . . ?
N2 N1 C9 C4 0.2(3) . . . . ?
Co1 N1 C9 C4 175.39(16) . . . . ?
N2 N1 C9 C8 -179.8(2) . . . . ?
Co1 N1 C9 C8 -4.7(3) . . . . ?
C3 C4 C9 N1 -0.1(3) . . . . ?
C5 C4 C9 N1 179.4(2) . . . . ?
C3 C4 C9 C8 180.0(2) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C7 C8 C9 N1 -179.6(2) . . . . ?
N3 C8 C9 N1 0.0(3) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
N3 C8 C9 C4 180.0(2) . . . . ?
C11 N4 C15 C14 -0.3(4) . . . . ?
Co1 N4 C15 C14 -176.5(2) . . . . ?
N4 C15 C14 C13 -0.8(5) . . . . ?
C15 C14 C13 C12 0.7(5) . . . . ?
C14 C13 C12 C11 0.6(5) . . . . ?
C15 N4 C11 C12 1.7(3) . . . . ?
Co1 N4 C11 C12 178.30(19) . . . . ?
C15 N4 C11 C10 -176.5(2) . . . . ?
Co1 N4 C11 C10 0.1(2) . . . . ?
C13 C12 C11 N4 -1.8(4) . . . . ?
C13 C12 C11 C10 176.2(2) . . . . ?
C8 N3 C10 C11 177.82(19) . . . . ?
Co1 N3 C10 C11 -2.6(3) . . . . ?
N4 C11 C10 N3 1.6(3) . . . . ?
C12 C11 C10 N3 -176.6(2) . . . . ?
C31 O30 C31 C32 168.6(17) 2_656 . . . ?

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
N2 H2 O1 0.88 1.88 2.752(4) 168.1 . yes
C3 H3 F4A^a 0.95 2.53 3.288(8) 136.4 . yes
C15 H15 F1 0.95 2.51 3.222(4) 131.3 6_565 yes
C12 H12 F4A^a 0.95 2.57 3.441(9) 152.0 3_545 yes
C10 H10 F3A^a 0.95 2.40 3.306(5) 158.3 3_545 yes
C20 H1B F4B^b 0.98 2.68 3.62(2) 161.5 . yes
C20 H1C F3B^b 0.98 2.68 3.171(17) 111.5 4_545 yes
O1 H1 F2A^a 0.956(10) 2.00(6) 2.798(5) 139(7) 4_545 yes
O1 H1 F3B^b 0.956(10) 2.24(8) 2.896(19) 125(7) 4_545 yes
O1 H1 F4B^b 0.956(10) 2.48(6) 3.26(2) 140(7) 4_545 yes

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/diethyl ether'
####################################################################### 
# 
# 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_JMSV14sq
_database_code_depnum_ccdc_archive 'CCDC 1906399'
loop_
_audit_author_name
_audit_author_address
'Naytze Ortiz-Pastrana'
;Centro de Investigacion y de Estudios Avanzados del IPN
Mexico
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-04 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         'C31 H25 B2 Co F8 N6 O'
_chemical_formula_sum            'C31 H25 B2 Co F8 N6 O'
_chemical_formula_weight         730.12

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'
B B 0.0013 0.0007 '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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.1427(7)
_cell_length_b                   15.5443(9)
_cell_length_c                   19.5164(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.570(2)
_cell_angle_gamma                90
_cell_volume                     3530.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.3096
_cell_measurement_theta_max      23.9850

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent blue'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   0.6496
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.562
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_T_max  0.7458
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            113448
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6231
_reflns_number_gt                4656
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1009P)²+6.3032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6231
_refine_ls_number_parameters     516
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1709
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      1.029
_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
Co1 Co 0.42222(4) 0.40939(3) 0.20295(3) 0.0402(2) Uani 1 1 d . . . . .
N1 N 0.4260(3) 0.3185(2) 0.13495(17) 0.0451(8) Uani 1 1 d . . . . .
C8 C 0.3781(4) 0.1570(3) 0.2583(2) 0.0536(11) Uani 1 1 d . . . . .
H8 H 0.3654 0.1542 0.3030 0.064 Uiso 1 1 calc R U . . .
N2 N 0.3974(3) 0.3170(2) 0.26035(17) 0.0414(7) Uani 1 1 d . . . . .
C2 C 0.4420(4) 0.3245(3) 0.0708(2) 0.0582(11) Uani 1 1 d . . . . .
H2 H 0.4489 0.3787 0.0522 0.070 Uiso 1 1 calc R U . . .
N3 N 0.4147(3) 0.4770(2) 0.28568(18) 0.0455(8) Uani 1 1 d . . . . .
C3 C 0.4488(5) 0.2526(3) 0.0306(3) 0.0765(15) Uani 1 1 d . . . . .
H3 H 0.4626 0.2590 -0.0136 0.092 Uiso 1 1 calc R U . . .
C4 C 0.4354(5) 0.1724(3) 0.0554(3) 0.0695(14) Uani 1 1 d . . . . .
H4 H 0.4396 0.1242 0.0281 0.083 Uiso 1 1 calc R U . . .
C5 C 0.4150(4) 0.1632(3) 0.1225(2) 0.0523(10) Uani 1 1 d . . . . .
C6 C 0.3986(4) 0.0838(3) 0.1531(3) 0.0626(12) Uani 1 1 d . . . . .
H6 H 0.3997 0.0328 0.1285 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3810(4) 0.0825(3) 0.2195(3) 0.0652(13) Uani 1 1 d . . . . .
H7 H 0.3706 0.0297 0.2393 0.078 Uiso 1 1 calc R U . . .
C9 C 0.3943(3) 0.2348(2) 0.2296(2) 0.0423(9) Uani 1 1 d . . . . .
C10 C 0.4118(3) 0.2386(2) 0.1609(2) 0.0443(9) Uani 1 1 d . . . . .
N23 N 0.2621(3) 0.4348(2) 0.15533(16) 0.0426(7) Uani 1 1 d . . . . .
C23 C 0.7742(4) 0.3618(4) 0.3070(4) 0.0885(18) Uani 1 1 d . . . . .
H23 H 0.8190 0.3241 0.3405 0.106 Uiso 1 1 calc R U . . .
C24 C 0.8246(5) 0.4229(4) 0.2776(4) 0.0895(19) Uani 1 1 d . . . . .
H24 H 0.9043 0.4270 0.2906 0.107 Uiso 1 1 calc R U . . .
C25 C 0.7573(4) 0.4813(3) 0.2269(3) 0.0690(14) Uani 1 1 d . . . . .
C26 C 0.7979(5) 0.5478(5) 0.1915(4) 0.0927(19) Uani 1 1 d . . . . .
H26 H 0.8766 0.5564 0.2005 0.111 Uiso 1 1 calc R U . . .
C27 C 0.7223(6) 0.5999(4) 0.1438(4) 0.101(2) Uani 1 1 d . . . . .
H27 H 0.7511 0.6446 0.1223 0.121 Uiso 1 1 calc R U . . .
C28 C 0.6046(5) 0.5884(3) 0.1267(3) 0.0790(16) Uani 1 1 d . . . . .
H28 H 0.5558 0.6243 0.0935 0.095 Uiso 1 1 calc R U . . .
C30 C 0.6375(4) 0.4702(3) 0.2090(2) 0.0544(11) Uani 1 1 d . . . . .
C31 C 0.3541(4) 0.5447(3) 0.1032(2) 0.0517(10) Uani 1 1 d . . . . .
H31 H 0.3580 0.6067 0.1128 0.062 Uiso 1 1 calc R U . . .
C32 C 0.2472(4) 0.5065(3) 0.1140(2) 0.0470(9) Uani 1 1 d . . . . .
C33 C 0.1373(4) 0.5394(3) 0.0844(2) 0.0623(13) Uani 1 1 d . . . . .
H33 H 0.1271 0.5898 0.0577 0.075 Uiso 1 1 calc R U . . .
C34 C 0.0444(4) 0.4972(4) 0.0947(3) 0.0687(14) Uani 1 1 d . . . . .
H34 H -0.0293 0.5188 0.0752 0.082 Uiso 1 1 calc R U . . .
C35 C 0.0610(4) 0.4233(4) 0.1335(3) 0.0652(13) Uani 1 1 d . . . . .
H35 H -0.0017 0.3931 0.1396 0.078 Uiso 1 1 calc R U . . .
C36 C 0.1704(4) 0.3933(3) 0.1638(2) 0.0502(10) Uani 1 1 d . . . . .
H36 H 0.1810 0.3431 0.1909 0.060 Uiso 1 1 calc R U . . .
C37 C 0.3003(7) 0.5893(5) -0.0222(4) 0.121(3) Uani 1 1 d . . . . .
H37A H 0.3232 0.5803 -0.0649 0.182 Uiso 1 1 calc R U . . .
H37B H 0.3234 0.6458 -0.0038 0.182 Uiso 1 1 calc R U . . .
H37C H 0.2184 0.5841 -0.0331 0.182 Uiso 1 1 calc R U . . .
C29 C 0.5596(4) 0.5237(3) 0.1588(2) 0.0538(10) Uani 1 1 d . . . . .
N22 N 0.4477(3) 0.5020(2) 0.1489(2) 0.0534(9) Uani 1 1 d . . . . .
C22 C 0.6551(4) 0.3548(3) 0.2872(3) 0.0668(13) Uani 1 1 d . . . . .
H22 H 0.6214 0.3124 0.3082 0.080 Uiso 1 1 calc R U . . .
N21 N 0.5885(3) 0.4068(2) 0.23949(19) 0.0495(8) Uani 1 1 d . . . . .
B11 B 0.1119(7) 0.2944(5) 0.3419(5) 0.0935(19) Uani 1 1 d . U . . .
F11 F 0.1382(10) 0.3746(8) 0.3324(7) 0.094(3) Uani 0.535(5) 1 d . U P A 1
F12 F 0.1961(9) 0.2387(7) 0.3468(9) 0.134(3) Uani 0.535(5) 1 d . U P A 1
F13 F 0.0357(12) 0.2625(8) 0.2724(7) 0.175(4) Uani 0.535(5) 1 d . U P A 1
F14 F 0.0396(9) 0.2869(7) 0.3822(5) 0.105(3) Uani 0.535(5) 1 d . U P A 1
F15 F 0.2121(7) 0.2795(7) 0.4041(6) 0.117(3) Uani 0.465(5) 1 d . U P A 2
F16 F 0.1053(14) 0.3707(12) 0.3085(8) 0.110(4) Uani 0.465(5) 1 d . U P A 2
F17 F 0.1436(11) 0.2412(6) 0.2961(6) 0.110(3) Uani 0.465(5) 1 d . U P A 2
F18 F 0.0179(12) 0.2628(9) 0.3485(8) 0.119(4) Uani 0.465(5) 1 d . U P A 2
B21 B 0.5964(7) 0.2382(5) 0.4742(4) 0.0853(18) Uani 1 1 d . U . . .
F21 F 0.5648(6) 0.1999(5) 0.4073(4) 0.110(2) Uani 0.535(5) 1 d . U P A 1
F22 F 0.6228(10) 0.3223(6) 0.4570(5) 0.126(3) Uani 0.535(5) 1 d . U P A 1
F23 F 0.6752(9) 0.1998(9) 0.5192(6) 0.141(3) Uani 0.535(5) 1 d . U P A 1
F24 F 0.5029(10) 0.2706(7) 0.4900(6) 0.134(3) Uani 0.535(5) 1 d . U P A 1
F25 F 0.4840(10) 0.2237(8) 0.4728(7) 0.127(3) Uani 0.465(5) 1 d . U P A 2
F26 F 0.6410(13) 0.2798(11) 0.4340(8) 0.160(4) Uani 0.465(5) 1 d . U P A 2
F27 F 0.6573(9) 0.2556(7) 0.5456(5) 0.117(3) Uani 0.465(5) 1 d . U P A 2
F28 F 0.6390(11) 0.1511(7) 0.4816(7) 0.139(3) Uani 0.465(5) 1 d . U P A 2
O19 O 0.3535(4) 0.5269(3) 0.0295(2) 0.0963(13) Uani 1 1 d . . . . .
C16 C 0.4253(4) 0.5616(3) 0.2952(3) 0.0574(11) Uani 1 1 d . . . . .
H16 H 0.4375 0.5957 0.2589 0.069 Uiso 1 1 calc R U . . .
C15 C 0.4185(4) 0.6001(3) 0.3576(3) 0.0705(14) Uani 1 1 d . . . . .
H15 H 0.4257 0.6594 0.3630 0.085 Uiso 1 1 calc R U . . .
C14 C 0.4013(5) 0.5508(4) 0.4111(3) 0.0749(15) Uani 1 1 d . . . . .
H14 H 0.3969 0.5763 0.4534 0.090 Uiso 1 1 calc R U . . .
C13 C 0.3903(4) 0.4621(3) 0.4025(2) 0.0642(12) Uani 1 1 d . . . . .
H13 H 0.3785 0.4274 0.4386 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3973(3) 0.4267(3) 0.3386(2) 0.0494(10) Uani 1 1 d . . . . .
C11 C 0.3886(3) 0.3365(3) 0.3224(2) 0.0478(10) Uani 1 1 d . . . . .
H11 H 0.3775 0.2954 0.3544 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N22 1.862(3) . ?
Co1 N2 1.898(3) . ?
Co1 N21 1.940(3) . ?
Co1 N23 1.941(3) . ?
Co1 N1 1.948(3) . ?
Co1 N3 1.950(3) . ?
N1 C2 1.325(5) . ?
N1 C10 1.371(5) . ?
C8 C9 1.368(5) . ?
C8 C7 1.390(7) . ?
C8 H8 0.9300 . ?
N2 C11 1.282(5) . ?
N2 C9 1.408(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
N3 C16 1.330(5) . ?
N3 C12 1.358(5) . ?
C3 C4 1.364(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(7) . ?
C4 H4 0.9300 . ?
C5 C10 1.397(6) . ?
C5 C6 1.408(6) . ?
C6 C7 1.372(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.418(6) . ?
N23 C36 1.337(5) . ?
N23 C32 1.357(5) . ?
C23 C24 1.345(8) . ?
C23 C22 1.391(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.417(8) . ?
C24 H24 0.9300 . ?
C25 C30 1.406(6) . ?
C25 C26 1.409(8) . ?
C26 C27 1.370(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(6) . ?
C28 H28 0.9300 . ?
C30 N21 1.373(5) . ?
C30 C29 1.420(6) . ?
C31 N22 1.396(5) . ?
C31 O19 1.463(6) . ?
C31 C32 1.497(6) . ?
C31 H31 0.9800 . ?
C32 C33 1.392(6) . ?
C33 C34 1.368(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.360(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 O19 1.417(7) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C29 N22 1.360(5) . ?
C22 N21 1.320(6) . ?
C22 H22 0.9300 . ?
B11 F18 1.283(15) . ?
B11 F11 1.313(15) . ?
B11 F12 1.322(12) . ?
B11 F14 1.341(13) . ?
B11 F16 1.345(19) . ?
B11 F17 1.351(12) . ?
B11 F15 1.472(12) . ?
B11 F13 1.490(15) . ?
B21 F26 1.251(14) . ?
B21 F23 1.251(11) . ?
B21 F24 1.355(12) . ?
B21 F25 1.376(13) . ?
B21 F21 1.385(10) . ?
B21 F27 1.406(12) . ?
B21 F22 1.408(12) . ?
B21 F28 1.442(13) . ?
C16 C15 1.381(7) . ?
C16 H16 0.9300 . ?
C15 C14 1.358(8) . ?
C15 H15 0.9300 . ?
C14 C13 1.390(7) . ?
C14 H14 0.9300 . ?
C13 C12 1.388(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.435(6) . ?
C11 H11 0.9300 . ?

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
N22 Co1 N2 178.38(15) . . ?
N22 Co1 N21 84.32(14) . . ?
N2 Co1 N21 95.23(14) . . ?
N22 Co1 N23 82.93(14) . . ?
N2 Co1 N23 97.49(13) . . ?
N21 Co1 N23 167.21(14) . . ?
N22 Co1 N1 97.78(15) . . ?
N2 Co1 N1 83.77(14) . . ?
N21 Co1 N1 90.63(14) . . ?
N23 Co1 N1 92.07(13) . . ?
N22 Co1 N3 96.14(15) . . ?
N2 Co1 N3 82.30(14) . . ?
N21 Co1 N3 89.80(14) . . ?
N23 Co1 N3 90.57(13) . . ?
N1 Co1 N3 166.05(14) . . ?
C2 N1 C10 118.8(4) . . ?
C2 N1 Co1 129.1(3) . . ?
C10 N1 Co1 112.1(3) . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C11 N2 C9 128.2(3) . . ?
C11 N2 Co1 116.7(3) . . ?
C9 N2 Co1 115.2(2) . . ?
N1 C2 C3 121.9(4) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C16 N3 C12 119.6(4) . . ?
C16 N3 Co1 128.5(3) . . ?
C12 N3 Co1 111.9(3) . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C10 C5 C6 118.6(4) . . ?
C10 C5 C4 116.9(4) . . ?
C6 C5 C4 124.5(4) . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 122.4(4) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C8 C9 N2 128.1(4) . . ?
C8 C9 C10 120.0(4) . . ?
N2 C9 C10 111.9(3) . . ?
N1 C10 C5 122.4(4) . . ?
N1 C10 C9 117.1(3) . . ?
C5 C10 C9 120.4(4) . . ?
C36 N23 C32 119.6(4) . . ?
C36 N23 Co1 126.8(3) . . ?
C32 N23 Co1 113.4(3) . . ?
C24 C23 C22 120.0(5) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C30 C25 C26 116.7(5) . . ?
C30 C25 C24 116.4(5) . . ?
C26 C25 C24 126.8(5) . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 122.2(5) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 H27 118.9 . . ?
C29 C28 C27 120.1(6) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
N21 C30 C25 121.7(4) . . ?
N21 C30 C29 115.7(4) . . ?
C25 C30 C29 122.6(4) . . ?
N22 C31 O19 108.2(4) . . ?
N22 C31 C32 107.6(3) . . ?
O19 C31 C32 107.6(4) . . ?
N22 C31 H31 111.1 . . ?
O19 C31 H31 111.1 . . ?
C32 C31 H31 111.1 . . ?
N23 C32 C33 119.9(4) . . ?
N23 C32 C31 115.8(4) . . ?
C33 C32 C31 124.2(4) . . ?
C34 C33 C32 119.7(5) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 119.4(5) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 119.8(5) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
N23 C36 C35 121.4(4) . . ?
N23 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
O19 C37 H37A 109.5 . . ?
O19 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O19 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N22 C29 C28 128.8(5) . . ?
N22 C29 C30 113.3(4) . . ?
C28 C29 C30 118.0(4) . . ?
C29 N22 C31 124.9(4) . . ?
C29 N22 Co1 115.6(3) . . ?
C31 N22 Co1 119.5(3) . . ?
N21 C22 C23 121.9(5) . . ?
N21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 N21 C30 119.4(4) . . ?
C22 N21 Co1 129.5(3) . . ?
C30 N21 Co1 111.1(3) . . ?
F11 B11 F12 114.7(9) . . ?
F11 B11 F14 113.1(10) . . ?
F12 B11 F14 121.5(9) . . ?
F18 B11 F16 117.0(11) . . ?
F18 B11 F17 105.3(10) . . ?
F16 B11 F17 102.0(11) . . ?
F18 B11 F15 114.0(10) . . ?
F16 B11 F15 117.3(10) . . ?
F17 B11 F15 97.2(8) . . ?
F11 B11 F13 107.4(9) . . ?
F12 B11 F13 96.6(10) . . ?
F14 B11 F13 99.5(9) . . ?
F23 B21 F24 122.7(10) . . ?
F26 B21 F25 132.5(11) . . ?
F23 B21 F21 114.0(10) . . ?
F24 B21 F21 110.4(8) . . ?
F26 B21 F27 108.8(10) . . ?
F25 B21 F27 106.8(9) . . ?
F23 B21 F22 115.5(10) . . ?
F24 B21 F22 88.5(9) . . ?
F21 B21 F22 101.3(7) . . ?
F26 B21 F28 109.9(11) . . ?
F25 B21 F28 100.0(9) . . ?
F27 B21 F28 90.5(8) . . ?
C37 O19 C31 116.4(5) . . ?
N3 C16 C15 121.6(5) . . ?
N3 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C12 C13 C14 118.3(5) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
N3 C12 C13 121.1(4) . . ?
N3 C12 C11 114.4(4) . . ?
C13 C12 C11 124.5(4) . . ?
N2 C11 C12 114.7(4) . . ?
N2 C11 H11 122.6 . . ?
C12 C11 H11 122.6 . . ?

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
N21 Co1 N2 C11 88.4(3) . . . . ?
N23 Co1 N2 C11 -90.3(3) . . . . ?
N1 Co1 N2 C11 178.5(3) . . . . ?
N3 Co1 N2 C11 -0.7(3) . . . . ?
N21 Co1 N2 C9 -89.8(3) . . . . ?
N23 Co1 N2 C9 91.5(3) . . . . ?
N1 Co1 N2 C9 0.2(3) . . . . ?
N3 Co1 N2 C9 -178.9(3) . . . . ?
C10 N1 C2 C3 -2.3(7) . . . . ?
Co1 N1 C2 C3 176.2(4) . . . . ?
N1 C2 C3 C4 2.1(9) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C3 C4 C5 C10 -1.1(7) . . . . ?
C3 C4 C5 C6 179.3(5) . . . . ?
C10 C5 C6 C7 -0.5(7) . . . . ?
C4 C5 C6 C7 179.1(5) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C9 C8 C7 C6 -0.5(7) . . . . ?
C7 C8 C9 N2 -178.3(4) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C11 N2 C9 C8 1.9(7) . . . . ?
Co1 N2 C9 C8 179.9(3) . . . . ?
C11 N2 C9 C10 -177.5(4) . . . . ?
Co1 N2 C9 C10 0.5(4) . . . . ?
C2 N1 C10 C5 0.8(6) . . . . ?
Co1 N1 C10 C5 -178.0(3) . . . . ?
C2 N1 C10 C9 -179.7(4) . . . . ?
Co1 N1 C10 C9 1.5(4) . . . . ?
C6 C5 C10 N1 -179.5(4) . . . . ?
C4 C5 C10 N1 0.9(6) . . . . ?
C6 C5 C10 C9 1.0(6) . . . . ?
C4 C5 C10 C9 -178.6(4) . . . . ?
C8 C9 C10 N1 179.2(3) . . . . ?
N2 C9 C10 N1 -1.4(5) . . . . ?
C8 C9 C10 C5 -1.3(6) . . . . ?
N2 C9 C10 C5 178.2(3) . . . . ?
C22 C23 C24 C25 0.6(10) . . . . ?
C23 C24 C25 C30 -1.1(9) . . . . ?
C23 C24 C25 C26 -179.4(6) . . . . ?
C30 C25 C26 C27 2.1(9) . . . . ?
C24 C25 C26 C27 -179.6(6) . . . . ?
C25 C26 C27 C28 -2.1(11) . . . . ?
C26 C27 C28 C29 1.1(10) . . . . ?
C26 C25 C30 N21 179.2(5) . . . . ?
C24 C25 C30 N21 0.7(7) . . . . ?
C26 C25 C30 C29 -1.2(7) . . . . ?
C24 C25 C30 C29 -179.7(5) . . . . ?
C36 N23 C32 C33 3.9(5) . . . . ?
Co1 N23 C32 C33 -171.3(3) . . . . ?
C36 N23 C32 C31 -175.6(3) . . . . ?
Co1 N23 C32 C31 9.2(4) . . . . ?
N22 C31 C32 N23 -8.8(5) . . . . ?
O19 C31 C32 N23 107.6(4) . . . . ?
N22 C31 C32 C33 171.7(4) . . . . ?
O19 C31 C32 C33 -71.9(5) . . . . ?
N23 C32 C33 C34 -2.6(6) . . . . ?
C31 C32 C33 C34 176.8(4) . . . . ?
C32 C33 C34 C35 -0.3(7) . . . . ?
C33 C34 C35 C36 2.0(7) . . . . ?
C32 N23 C36 C35 -2.2(6) . . . . ?
Co1 N23 C36 C35 172.3(3) . . . . ?
C34 C35 C36 N23 -0.8(7) . . . . ?
C27 C28 C29 N22 -179.6(5) . . . . ?
C27 C28 C29 C30 -0.3(8) . . . . ?
N21 C30 C29 N22 -0.6(6) . . . . ?
C25 C30 C29 N22 179.8(4) . . . . ?
N21 C30 C29 C28 180.0(4) . . . . ?
C25 C30 C29 C28 0.4(7) . . . . ?
C28 C29 N22 C31 -1.4(8) . . . . ?
C30 C29 N22 C31 179.3(4) . . . . ?
C28 C29 N22 Co1 179.9(4) . . . . ?
C30 C29 N22 Co1 0.5(5) . . . . ?
O19 C31 N22 C29 69.9(5) . . . . ?
C32 C31 N22 C29 -174.1(4) . . . . ?
O19 C31 N22 Co1 -111.4(4) . . . . ?
C32 C31 N22 Co1 4.6(5) . . . . ?
N21 Co1 N22 C29 -0.2(3) . . . . ?
N23 Co1 N22 C29 178.8(3) . . . . ?
N1 Co1 N22 C29 -90.1(3) . . . . ?
N3 Co1 N22 C29 88.9(3) . . . . ?
N21 Co1 N22 C31 -179.1(3) . . . . ?
N23 Co1 N22 C31 -0.1(3) . . . . ?
N1 Co1 N22 C31 91.1(3) . . . . ?
N3 Co1 N22 C31 -89.9(3) . . . . ?
C24 C23 C22 N21 0.4(9) . . . . ?
C23 C22 N21 C30 -0.8(8) . . . . ?
C23 C22 N21 Co1 179.5(4) . . . . ?
C25 C30 N21 C22 0.3(7) . . . . ?
C29 C30 N21 C22 -179.3(4) . . . . ?
C25 C30 N21 Co1 -180.0(4) . . . . ?
C29 C30 N21 Co1 0.4(5) . . . . ?
N22 C31 O19 C37 -154.0(5) . . . . ?
C32 C31 O19 C37 90.0(6) . . . . ?
C12 N3 C16 C15 -0.3(6) . . . . ?
Co1 N3 C16 C15 -179.6(3) . . . . ?
N3 C16 C15 C14 0.4(7) . . . . ?
C16 C15 C14 C13 -0.2(8) . . . . ?
C15 C14 C13 C12 0.0(8) . . . . ?
C16 N3 C12 C13 0.0(6) . . . . ?
Co1 N3 C12 C13 179.4(3) . . . . ?
C16 N3 C12 C11 -179.3(4) . . . . ?
Co1 N3 C12 C11 0.1(4) . . . . ?
C14 C13 C12 N3 0.2(7) . . . . ?
C14 C13 C12 C11 179.4(4) . . . . ?
C9 N2 C11 C12 178.9(3) . . . . ?
Co1 N2 C11 C12 0.9(4) . . . . ?
N3 C12 C11 N2 -0.7(5) . . . . ?
C13 C12 C11 N2 -179.9(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
C2 H2 N22 0.93 2.69 3.144(6) 110.7 .
C2 H2 O19 0.93 2.56 3.347(6) 142.8 .
C3 H3 F14 0.93 2.57 3.436(11) 155.2 4_665
C23 H23 F14 0.93 2.63 3.347(12) 134.1 1_655
C23 H23 F18 0.93 2.56 3.226(15) 129.0 1_655
C31 H31 F12 0.98 2.36 3.279(10) 156.4 2
C33 H33 F25 0.93 2.46 3.269(12) 145.6 2
C36 H36 N2 0.93 2.62 3.097(5) 112.3 .
C22 H22 N2 0.93 2.61 3.079(6) 111.6 .
C22 H22 F26 0.93 2.45 3.144(14) 131.2 .
C16 H16 N22 0.93 2.63 3.086(6) 111.2 .
C16 H16 F17 0.93 2.58 3.289(10) 133.8 2
C15 H15 F27 0.93 2.64 3.231(11) 122.1 3_666
C11 H11 F12 0.93 2.34 2.939(10) 122.1 .
C11 H11 F15 0.93 2.48 3.142(10) 128.3 .
C11 H11 F25 0.93 2.56 3.330(13) 140.6 .

_refine_diff_density_max         0.945
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.068


