# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1972230'
loop_
_audit_author_name
_audit_author_address
'Atsushi Kondo'
;SEIKEI University
Japan
;
_audit_update_record             
;
2019-12-16 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 B2 Cu F12 N4 O2'
_chemical_formula_weight         765.70

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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.440(3)
_cell_length_b                   15.070(3)
_cell_length_c                   16.390(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.68(3)
_cell_angle_gamma                90
_cell_volume                     3378.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    3007
_cell_measurement_theta_min      2.011
_cell_measurement_theta_max      25.108

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             1548
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            15683
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         25.108
_diffrn_reflns_theta_full        25.108
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3007
_reflns_number_gt                2301
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1133P)²+31.3887P] 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         3007
_refine_ls_number_parameters     223
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.2029
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.119
_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
C12 C 0.1578(6) 0.1281(6) 0.4314(6) 0.068(2) Uani 1 1 d . U . . .
O1 O 0.2185(5) 0.0909(5) 0.4887(5) 0.087(2) Uani 1 1 d . U . . .
Cu1 Cu 0.5000 0.24931(5) 0.2500 0.0202(3) Uani 1 2 d S TU P . .
N1 N 0.5029(3) 0.3435(3) 0.3392(2) 0.0215(8) Uani 1 1 d . U . . .
C3 C 0.5007(4) 0.4676(3) 0.4661(3) 0.0216(10) Uani 1 1 d . U . . .
C1 C 0.5727(4) 0.3448(4) 0.4152(3) 0.0304(11) Uani 1 1 d . U . . .
H1 H 0.6237 0.3021 0.4262 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4319(4) 0.4045(3) 0.3251(3) 0.0284(11) Uani 1 1 d . U . . .
H5 H 0.3820 0.4051 0.2707 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4279(4) 0.4664(3) 0.3860(3) 0.0291(11) Uani 1 1 d . U . . .
H4 H 0.3758 0.5080 0.3733 0.035 Uiso 1 1 calc R U . . .
F3 F 0.8125(3) 0.1684(3) 0.3233(3) 0.0639(12) Uani 1 1 d . U . . .
F1 F 0.6782(2) 0.2555(2) 0.3001(2) 0.0428(8) Uani 1 1 d . U . . .
F2 F 0.8126(5) 0.2790(6) 0.4303(4) 0.130(3) Uani 1 1 d . U . . .
F5 F 0.9286(4) 0.3338(5) 0.3399(7) 0.166(4) Uani 1 1 d . U . . .
F6 F 0.8009(5) 0.4106(4) 0.3218(6) 0.139(3) Uani 1 1 d . U . . .
F4 F 0.7933(7) 0.3006(8) 0.2096(5) 0.189(4) Uani 1 1 d . U . . .
B1 B 0.7812(8) 0.2537(7) 0.3312(8) 0.075(3) Uani 1 1 d . U . . .
C14 C 0.8323(8) 0.3297(8) 0.3047(10) 0.121(4) Uani 1 1 d . U . . .
C6 C 0.4269(4) 0.1507(4) 0.3710(4) 0.0402(13) Uani 1 1 d . U . . .
H6 H 0.3741 0.1912 0.3510 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4245(5) 0.0911(4) 0.4329(4) 0.0427(14) Uani 1 1 d . U . . .
H7 H 0.3701 0.0902 0.4536 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4997(4) 0.0325(3) 0.4654(3) 0.0324(12) Uani 1 1 d . U . . .
C10 C 0.5719(5) 0.0983(5) 0.3678(5) 0.0541(16) Uani 1 1 d . U . . .
H10 H 0.6252 0.1006 0.3457 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5745(5) 0.0358(5) 0.4304(5) 0.0576(17) Uani 1 1 d . U . . .
H9 H 0.6277 -0.0046 0.4491 0.069 Uiso 1 1 calc R U . . .
N2 N 0.4990(3) 0.1553(3) 0.3371(3) 0.0261(9) Uani 1 1 d . U . . .
C13 C 0.1250(13) 0.0945(12) 0.3442(8) 0.180(7) Uani 1 1 d . U . . .
H13A H 0.1565 0.1280 0.3091 0.269 Uiso 1 1 calc R U . . .
H13B H 0.0539 0.1010 0.3200 0.269 Uiso 1 1 calc R U . . .
H13C H 0.1425 0.0316 0.3444 0.269 Uiso 1 1 calc R U . . .
C11 C 0.1182(11) 0.2109(9) 0.4528(11) 0.142(5) Uani 1 1 d . U . . .
H11A H 0.1486 0.2237 0.5142 0.214 Uiso 1 1 calc R U . . .
H11B H 0.0473 0.2051 0.4398 0.214 Uiso 1 1 calc R U . . .
H11C H 0.1321 0.2595 0.4186 0.214 Uiso 1 1 calc R U . . .
C2 C 0.5746(4) 0.4051(3) 0.4788(3) 0.0310(12) Uani 1 1 d . U . . .
H2 H 0.6268 0.4039 0.5317 0.037 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
C12 O1 1.199(10) . ?
C12 C13 1.446(15) . ?
C12 C11 1.460(15) . ?
Cu1 N2 2.014(4) . ?
Cu1 N2 2.014(4) 2_655 ?
Cu1 N1 2.029(4) . ?
Cu1 N1 2.029(4) 2_655 ?
N1 C1 1.329(6) . ?
N1 C5 1.340(6) . ?
C3 C2 1.388(7) . ?
C3 C4 1.395(7) . ?
C3 C3 1.485(9) 5_666 ?
C1 C2 1.376(7) . ?
C1 H1 0.9500 . ?
C5 C4 1.381(7) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
F3 B1 1.382(10) . ?
F1 B1 1.410(11) . ?
F2 B1 1.588(14) . ?
F5 C14 1.326(12) . ?
F6 C14 1.360(13) . ?
F4 C14 1.541(16) . ?
B1 C14 1.500(17) . ?
C6 N2 1.331(7) . ?
C6 C7 1.363(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.368(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(8) . ?
C8 C8 1.498(10) 5_656 ?
C10 N2 1.326(8) . ?
C10 C9 1.385(9) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C12 C13 122.4(12) . . ?
O1 C12 C11 117.1(11) . . ?
C13 C12 C11 120.5(13) . . ?
N2 Cu1 N2 90.6(2) . 2_655 ?
N2 Cu1 N1 89.16(16) . . ?
N2 Cu1 N1 178.49(17) 2_655 . ?
N2 Cu1 N1 178.49(17) . 2_655 ?
N2 Cu1 N1 89.16(16) 2_655 2_655 ?
N1 Cu1 N1 91.1(2) . 2_655 ?
C1 N1 C5 117.5(4) . . ?
C1 N1 Cu1 121.3(3) . . ?
C5 N1 Cu1 121.2(3) . . ?
C2 C3 C4 116.4(4) . . ?
C2 C3 C3 121.9(5) . 5_666 ?
C4 C3 C3 121.7(5) . 5_666 ?
N1 C1 C2 122.9(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
F3 B1 F1 108.9(8) . . ?
F3 B1 C14 118.5(9) . . ?
F1 B1 C14 116.1(8) . . ?
F3 B1 F2 109.0(8) . . ?
F1 B1 F2 106.7(8) . . ?
C14 B1 F2 96.1(10) . . ?
F5 C14 F6 103.9(10) . . ?
F5 C14 B1 117.0(11) . . ?
F6 C14 B1 113.5(11) . . ?
F5 C14 F4 116.4(12) . . ?
F6 C14 F4 115.2(11) . . ?
B1 C14 F4 91.2(10) . . ?
N2 C6 C7 123.7(5) . . ?
N2 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C6 C7 C8 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 116.5(5) . . ?
C7 C8 C8 121.9(6) . 5_656 ?
C9 C8 C8 121.6(6) . 5_656 ?
N2 C10 C9 123.5(6) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C8 C9 C10 119.6(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C10 N2 C6 116.1(5) . . ?
C10 N2 Cu1 122.6(4) . . ?
C6 N2 Cu1 121.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(8) . . . . ?
Cu1 N1 C1 C2 -176.9(4) . . . . ?
C1 N1 C5 C4 -1.0(8) . . . . ?
Cu1 N1 C5 C4 176.0(4) . . . . ?
N1 C5 C4 C3 0.6(8) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C3 C4 C5 -179.5(6) 5_666 . . . ?
F3 B1 C14 F5 -53.8(18) . . . . ?
F1 B1 C14 F5 173.6(11) . . . . ?
F2 B1 C14 F5 61.7(13) . . . . ?
F3 B1 C14 F6 -174.9(9) . . . . ?
F1 B1 C14 F6 52.6(16) . . . . ?
F2 B1 C14 F6 -59.4(11) . . . . ?
F3 B1 C14 F4 66.9(11) . . . . ?
F1 B1 C14 F4 -65.7(11) . . . . ?
F2 B1 C14 F4 -177.6(6) . . . . ?
N2 C6 C7 C8 1.4(11) . . . . ?
C6 C7 C8 C9 -1.9(10) . . . . ?
C6 C7 C8 C8 178.7(7) . . . 5_656 ?
C7 C8 C9 C10 2.1(11) . . . . ?
C8 C8 C9 C10 -178.6(8) 5_656 . . . ?
N2 C10 C9 C8 -1.8(13) . . . . ?
C9 C10 N2 C6 1.1(11) . . . . ?
C9 C10 N2 Cu1 177.1(6) . . . . ?
C7 C6 N2 C10 -0.9(10) . . . . ?
C7 C6 N2 Cu1 -177.0(5) . . . . ?
N1 C1 C2 C3 1.1(9) . . . . ?
C4 C3 C2 C1 -1.4(8) . . . . ?
C3 C3 C2 C1 178.7(6) 5_666 . . . ?

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
C1 H1 F1 0.95 2.54 3.087(6) 117.2 .
C1 H1 F2 0.95 2.55 3.153(7) 121.9 7_656
C5 H5 F1 0.95 2.56 3.112(6) 117.5 2_655
C5 H5 F6 0.95 2.59 3.452(8) 150.9 2_655
C4 H4 F3 0.95 2.62 3.464(6) 148.1 3_455
C6 H6 F1 0.95 2.54 3.151(7) 122.5 2_655
C13 H13A F3 0.98 2.43 3.343(13) 155.0 2_655
C2 H2 F3 0.95 2.50 3.320(6) 144.1 7_656
C1 H1 F1 0.95 2.54 3.087(6) 117.2 .
C1 H1 F2 0.95 2.55 3.153(7) 121.9 7_656
C5 H5 F1 0.95 2.56 3.112(6) 117.5 2_655
C5 H5 F6 0.95 2.59 3.452(8) 150.9 2_655
C4 H4 F3 0.95 2.62 3.464(6) 148.1 3_455
C6 H6 F1 0.95 2.54 3.151(7) 122.5 2_655
C13 H13A F3 0.98 2.43 3.343(13) 155.0 2_655
C2 H2 F3 0.95 2.50 3.320(6) 144.1 7_656

_refine_diff_density_max         1.570
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.120

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'chemical reaction in a solvent'
