# 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_ar
_database_code_depnum_ccdc_archive 'CCDC 2016184'
loop_
_audit_author_name
_audit_author_address
'Hai-Xia Zhang'
;FJIRSM
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 B Cu N6'
_chemical_formula_sum            'C9 H10 B Cu N6'
_chemical_formula_weight         276.58
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.014(6)
_cell_length_b                   14.104(10)
_cell_length_c                   10.095(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.207(11)
_cell_angle_gamma                90
_cell_volume                     1138.1(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7120
_cell_measurement_theta_min      2.0228
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    1.903
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7934
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.486
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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                1870
_reflns_number_total             2401
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.087
_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)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1201
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
2.a Ternary CH refined with riding coordinates:
 B00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cu01 Cu 0.06149(5) 0.40646(3) 0.45001(4) 0.04720(19) Uani 1 1 d . . . . .
N002 N 0.6671(3) 0.43839(18) 0.8128(2) 0.0376(5) Uani 1 1 d . . . . .
N003 N 0.3830(3) 0.35438(18) 0.7782(2) 0.0395(6) Uani 1 1 d . . . . .
N004 N 0.6466(3) 0.26077(17) 0.8440(2) 0.0369(6) Uani 1 1 d . . . . .
N005 N 0.8431(3) 0.15060(18) 0.8842(2) 0.0420(6) Uani 1 1 d . . . . .
N006 N 0.1762(3) 0.3703(2) 0.6206(3) 0.0474(6) Uani 1 1 d . . . . .
N007 N 0.8271(3) 0.53022(18) 0.6945(2) 0.0463(6) Uani 1 1 d . . . . .
C008 C 0.7823(4) 0.2332(2) 0.9200(3) 0.0421(7) Uani 1 1 d . . . . .
H008 H 0.829168 0.268774 0.990828 0.050 Uiso 1 1 calc R . . . .
C009 C 0.7291(4) 0.4550(2) 0.6944(3) 0.0398(7) Uani 1 1 d . . . . .
H009 H 0.705139 0.417168 0.619971 0.048 Uiso 1 1 calc R . . . .
C00A C 0.7309(4) 0.5091(3) 0.8942(3) 0.0540(9) Uani 1 1 d . . . . .
H00A H 0.710797 0.517677 0.983020 0.065 Uiso 1 1 calc R . . . .
C00B C 0.2397(4) 0.3189(2) 0.8253(3) 0.0518(8) Uani 1 1 d . . . . .
H00B H 0.229825 0.292634 0.908810 0.062 Uiso 1 1 calc R . . . .
C00C C 0.1152(4) 0.3291(3) 0.7285(3) 0.0522(9) Uani 1 1 d . . . . .
H00C H 0.004716 0.310595 0.734876 0.063 Uiso 1 1 calc R . . . .
C00D C 0.3363(4) 0.3837(3) 0.6541(3) 0.0514(9) Uani 1 1 d . . . . .
H00D H 0.409766 0.410631 0.597706 0.062 Uiso 1 1 calc R . . . .
C00E C 0.6192(5) 0.1892(3) 0.7534(3) 0.0581(10) Uani 1 1 d . . . . .
H00E H 0.532883 0.186496 0.686678 0.070 Uiso 1 1 calc R . . . .
C00F C 0.7399(5) 0.1231(3) 0.7780(4) 0.0581(10) Uani 1 1 d . . . . .
H00F H 0.750670 0.067475 0.729877 0.070 Uiso 1 1 calc R . . . .
C00G C 0.8285(5) 0.5643(3) 0.8221(4) 0.0599(10) Uani 1 1 d . . . . .
H00G H 0.887682 0.617283 0.854111 0.072 Uiso 1 1 calc R . . . .
B00H B 0.5547(4) 0.3571(2) 0.8584(3) 0.0386(8) Uani 1 1 d . . . . .
H00H H 0.536100 0.366740 0.952372 0.046 Uiso 1 1 calc R . . . .


_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
Cu01 Cu01 3.0164(18) 3_566 ?
Cu01 N005 1.995(3) 4_465 ?
Cu01 N006 1.959(3) . ?
Cu01 N007 1.979(3) 3_666 ?
N002 C009 1.348(4) . ?
N002 C00A 1.368(4) . ?
N002 B00H 1.549(4) . ?
N003 C00B 1.369(4) . ?
N003 C00D 1.346(4) . ?
N003 B00H 1.545(4) . ?
N004 C008 1.341(4) . ?
N004 C00E 1.369(4) . ?
N004 B00H 1.557(4) . ?
N005 C008 1.323(4) . ?
N005 C00F 1.362(4) . ?
N006 C00C 1.357(4) . ?
N006 C00D 1.316(4) . ?
N007 C009 1.320(4) . ?
N007 C00G 1.374(4) . ?
C00A C00G 1.354(5) . ?
C00B C00C 1.352(4) . ?
C00E C00F 1.354(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
N005 Cu01 Cu01 99.44(9) 4_465 3_566 ?
N006 Cu01 Cu01 94.44(9) . 3_566 ?
N006 Cu01 N005 122.07(11) . 4_465 ?
N006 Cu01 N007 123.90(12) . 3_666 ?
N007 Cu01 Cu01 91.61(9) 3_666 3_566 ?
N007 Cu01 N005 111.65(11) 3_666 4_465 ?
C009 N002 C00A 105.1(3) . . ?
C009 N002 B00H 130.7(3) . . ?
C00A N002 B00H 124.1(3) . . ?
C00B N003 B00H 124.4(3) . . ?
C00D N003 C00B 104.6(3) . . ?
C00D N003 B00H 131.0(3) . . ?
C008 N004 C00E 104.6(3) . . ?
C008 N004 B00H 124.7(2) . . ?
C00E N004 B00H 130.7(3) . . ?
C008 N005 Cu01 126.6(2) . 4_666 ?
C008 N005 C00F 104.5(3) . . ?
C00F N005 Cu01 127.9(2) . 4_666 ?
C00C N006 Cu01 130.1(2) . . ?
C00D N006 Cu01 125.0(2) . . ?
C00D N006 C00C 104.9(3) . . ?
C009 N007 Cu01 131.5(2) . 3_666 ?
C009 N007 C00G 104.2(3) . . ?
C00G N007 Cu01 124.1(2) . 3_666 ?
N005 C008 N004 113.5(3) . . ?
N007 C009 N002 113.4(3) . . ?
C00G C00A N002 107.5(3) . . ?
C00C C00B N003 107.7(3) . . ?
C00B C00C N006 109.6(3) . . ?
N006 C00D N003 113.2(3) . . ?
C00F C00E N004 107.9(3) . . ?
C00E C00F N005 109.4(3) . . ?
C00A C00G N007 109.7(3) . . ?
N002 B00H N004 109.2(3) . . ?
N003 B00H N002 112.2(2) . . ?
N003 B00H N004 109.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
