# 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 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2059565'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2020-12-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H16 B2 Cu N16'
_chemical_formula_sum            'C10 H16 B2 Cu N16'
_chemical_formula_weight         445.55
_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'
B B 0.0013 0.0007 '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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.507(3)
_cell_length_b                   8.2794(17)
_cell_length_c                   16.968(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1897.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5242
_cell_measurement_temperature    439.6
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.9272
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7226
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      439.6
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1719
_reflns_number_total             2169
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.1128
_refine_ls_restrained_S_all      1.310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+11.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 B1(H1D,H1E)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cu1 Cu 1.000000 0.000000 0.500000 0.0205(3) Uani 1 2 d S . P . .
N5 N 1.0557(4) 0.1235(6) 0.6624(3) 0.0254(12) Uani 1 1 d . . . . .
N3 N 1.1344(3) 0.0128(6) 0.4488(3) 0.0192(11) Uani 1 1 d . . . . .
N1 N 1.2583(4) 0.0658(7) 0.3730(3) 0.0233(12) Uani 1 1 d . . . . .
N4 N 1.0457(4) 0.1569(6) 0.5844(3) 0.0186(11) Uani 1 1 d . . . . .
N7 N 1.0990(4) 0.3692(6) 0.6444(3) 0.0200(12) Uani 1 1 d . . . . .
N6 N 1.0875(4) 0.2526(7) 0.6983(3) 0.0254(12) Uani 1 1 d . . . . .
N2 N 1.2977(4) -0.0216(7) 0.4327(3) 0.0332(14) Uani 1 1 d . . . . .
N8 N 0.9478(4) 0.2267(6) 0.4223(3) 0.0272(13) Uani 1 1 d . . . . .
C2 C 1.1620(5) 0.0862(8) 0.3831(4) 0.0209(14) Uani 1 1 d . . . . .
H2 H 1.119380 0.144242 0.348738 0.025 Uiso 1 1 calc R U . . .
C4 C 1.0728(5) 0.3090(7) 0.5752(4) 0.0197(13) Uani 1 1 d . . . . .
H4 H 1.073451 0.366167 0.526687 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9136(5) 0.3274(8) 0.3851(4) 0.0232(14) Uani 1 1 d . . . . .
C3 C 1.2206(5) -0.0502(9) 0.4765(4) 0.0294(16) Uani 1 1 d . . . . .
H3 H 1.224237 -0.110454 0.524049 0.035 Uiso 1 1 calc R U . . .
C1 C 1.3218(5) 0.1301(9) 0.3099(4) 0.0339(17) Uani 1 1 d . . . . .
H1A H 1.369301 0.206855 0.332306 0.051 Uiso 1 1 calc R U . . .
H1B H 1.280689 0.185286 0.270586 0.051 Uiso 1 1 calc R U . . .
H1C H 1.357627 0.041143 0.284651 0.051 Uiso 1 1 calc R U . . .
B1 B 1.1412(6) 0.5401(9) 0.6671(5) 0.0301(18) Uani 1 1 d . . . . .
H1D H 1.126434 0.561589 0.722041 0.036 Uiso 1 1 d R U . . .
H1E H 1.211775 0.546869 0.657171 0.036 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.015(5) 5_756 ?
Cu1 N3 2.015(5) . ?
Cu1 N4 2.030(5) . ?
Cu1 N4 2.030(5) 5_756 ?
Cu1 N8 2.400(6) 5_756 ?
Cu1 N8 2.400(6) . ?
N5 N4 1.360(7) . ?
N5 N6 1.303(7) . ?
N3 C2 1.322(7) . ?
N3 C3 1.360(8) . ?
N1 N2 1.355(7) . ?
N1 C2 1.323(8) . ?
N1 C1 1.471(8) . ?
N4 C4 1.321(7) . ?
N7 N6 1.339(7) . ?
N7 C4 1.323(7) . ?
N7 B1 1.573(9) . ?
N2 C3 1.301(8) . ?
N8 C5 1.143(8) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C5 B1 1.592(10) 5_766 ?
C3 H3 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
B1 H1D 0.9701 . ?
B1 H1E 0.9699 . ?

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 Cu1 N3 180.0(2) 5_756 . ?
N3 Cu1 N4 89.81(19) . . ?
N3 Cu1 N4 90.19(19) 5_756 . ?
N3 Cu1 N4 90.19(19) . 5_756 ?
N3 Cu1 N4 89.81(19) 5_756 5_756 ?
N3 Cu1 N8 90.8(2) . 5_756 ?
N3 Cu1 N8 89.2(2) 5_756 5_756 ?
N3 Cu1 N8 90.8(2) 5_756 . ?
N3 Cu1 N8 89.2(2) . . ?
N4 Cu1 N4 180.0 5_756 . ?
N4 Cu1 N8 88.64(19) 5_756 5_756 ?
N4 Cu1 N8 88.64(19) . . ?
N4 Cu1 N8 91.36(19) . 5_756 ?
N4 Cu1 N8 91.36(19) 5_756 . ?
N8 Cu1 N8 180.0 5_756 . ?
N6 N5 N4 108.7(5) . . ?
C2 N3 Cu1 129.9(4) . . ?
C2 N3 C3 103.1(5) . . ?
C3 N3 Cu1 127.0(4) . . ?
N2 N1 C1 120.6(5) . . ?
C2 N1 N2 110.9(5) . . ?
C2 N1 C1 128.5(6) . . ?
N5 N4 Cu1 125.9(4) . . ?
C4 N4 Cu1 127.7(4) . . ?
C4 N4 N5 106.3(5) . . ?
N6 N7 B1 121.6(5) . . ?
C4 N7 N6 107.7(5) . . ?
C4 N7 B1 130.7(5) . . ?
N5 N6 N7 108.1(5) . . ?
C3 N2 N1 102.1(5) . . ?
C5 N8 Cu1 173.0(5) . . ?
N3 C2 N1 109.2(6) . . ?
N3 C2 H2 125.4 . . ?
N1 C2 H2 125.4 . . ?
N4 C4 N7 109.2(5) . . ?
N4 C4 H4 125.4 . . ?
N7 C4 H4 125.4 . . ?
N8 C5 B1 175.9(7) . 5_766 ?
N3 C3 H3 122.6 . . ?
N2 C3 N3 114.8(6) . . ?
N2 C3 H3 122.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N7 B1 C5 108.4(5) . 5_766 ?
N7 B1 H1D 109.0 . . ?
N7 B1 H1E 111.5 . . ?
C5 B1 H1D 108.2 5_766 . ?
C5 B1 H1E 108.7 5_766 . ?
H1D B1 H1E 111.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N3 C2 N1 178.5(4) . . . . ?
Cu1 N3 C3 N2 -178.5(5) . . . . ?
Cu1 N4 C4 N7 -179.0(4) . . . . ?
N5 N4 C4 N7 0.1(7) . . . . ?
N1 N2 C3 N3 0.0(8) . . . . ?
N4 N5 N6 N7 -0.5(7) . . . . ?
N6 N5 N4 Cu1 179.4(4) . . . . ?
N6 N5 N4 C4 0.3(7) . . . . ?
N6 N7 C4 N4 -0.4(7) . . . . ?
N6 N7 B1 C5 -144.4(6) . . . 5_766 ?
N2 N1 C2 N3 -0.5(7) . . . . ?
C2 N3 C3 N2 -0.3(8) . . . . ?
C2 N1 N2 C3 0.3(7) . . . . ?
C4 N7 N6 N5 0.6(7) . . . . ?
C4 N7 B1 C5 38.4(10) . . . 5_766 ?
C3 N3 C2 N1 0.5(7) . . . . ?
C1 N1 N2 C3 177.8(6) . . . . ?
C1 N1 C2 N3 -177.8(6) . . . . ?
B1 N7 N6 N5 -177.2(6) . . . . ?
B1 N7 C4 N4 177.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
