# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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_201013e
_database_code_depnum_ccdc_archive 'CCDC 2059562'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 B Cu0.50 N7'
_chemical_formula_weight         221.78

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.2506(9)
_cell_length_b                   10.1588(11)
_cell_length_c                   10.8037(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.301(4)
_cell_angle_gamma                90.00
_cell_volume                     1017.11(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1718
_cell_measurement_theta_min      2.981
_cell_measurement_theta_max      27.27

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7329
_exptl_absorpt_correction_T_max  0.8976
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4940
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1785
_reflns_number_gt                1362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0995P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1785
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 1.0000 1.0000 0.0319(3) Uani 1 2 d S . .
N1 N 0.1124(4) 1.1516(4) 0.9734(4) 0.0482(10) Uani 1 1 d . . .
N2 N 0.3202(4) 1.0585(4) 1.0155(4) 0.0366(9) Uani 1 1 d . . .
N3 N 0.3768(4) 0.6166(4) 1.0512(3) 0.0354(9) Uani 1 1 d . . .
N4 N 0.4965(4) 0.6322(4) 1.1717(3) 0.0411(9) Uani 1 1 d . . .
N5 N 0.5485(4) 0.7491(4) 1.1706(4) 0.0428(9) Uani 1 1 d . . .
N6 N 0.4648(4) 0.8114(3) 1.0512(3) 0.0331(8) Uani 1 1 d . . .
N7 N 0.1427(5) 0.4508(5) 0.7432(4) 0.0476(10) Uani 1 1 d . . .
B1 B 0.2847(8) 0.4855(6) 1.0210(6) 0.0488(16) Uani 1 1 d . . .
H1A H 0.2149 0.4914 1.0594 0.059 Uiso 1 1 calc R . .
H1B H 0.3473 0.4109 1.0622 0.059 Uiso 1 1 calc R . .
C1 C 0.2096(5) 1.1243(5) 0.9247(5) 0.0427(11) Uani 1 1 d . . .
H1 H 0.2003 1.1486 0.8383 0.051 Uiso 1 1 calc R . .
C2 C 0.2910(6) 1.0418(6) 1.1274(5) 0.0482(12) Uani 1 1 d . . .
H2 H 0.3497 0.9983 1.2078 0.058 Uiso 1 1 calc R . .
C3 C 0.1622(6) 1.0994(5) 1.1012(5) 0.0539(14) Uani 1 1 d . . .
H3 H 0.1168 1.1024 1.1595 0.065 Uiso 1 1 calc R . .
C4 C -0.0220(6) 1.2267(6) 0.9017(7) 0.0719(18) Uani 1 1 d . . .
H4A H -0.0147 1.3093 0.9473 0.108 Uiso 1 1 calc R . .
H4B H -0.1016 1.1773 0.9022 0.108 Uiso 1 1 calc R . .
H4C H -0.0372 1.2424 0.8089 0.108 Uiso 1 1 calc R . .
C5 C 0.3589(5) 0.7278(4) 0.9798(4) 0.0347(10) Uani 1 1 d . . .
H5 H 0.2845 0.7443 0.8940 0.042 Uiso 1 1 calc R . .
C6 C 0.2040(5) 0.4670(4) 0.8594(5) 0.0372(11) 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
Cu1 N2 2.010(4) 3_677 ?
Cu1 N2 2.010(4) . ?
Cu1 N6 2.068(3) 3_677 ?
Cu1 N6 2.068(3) . ?
Cu1 N7 2.451(4) 2_556 ?
Cu1 N7 2.451(4) 4_676 ?
N1 C1 1.339(6) . ?
N1 C3 1.359(6) . ?
N1 C4 1.472(7) . ?
N2 C1 1.321(6) . ?
N2 C2 1.375(6) . ?
N3 C5 1.335(5) . ?
N3 N4 1.364(5) . ?
N3 B1 1.584(6) . ?
N4 N5 1.304(5) . ?
N5 N6 1.362(5) . ?
N6 C5 1.334(5) . ?
N7 C6 1.151(6) . ?
N7 Cu1 2.451(4) 2_546 ?
B1 C6 1.591(7) . ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
C1 H1 0.9300 . ?
C2 C3 1.359(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5 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 Cu1 N2 180.000(1) 3_677 . ?
N2 Cu1 N6 88.89(15) 3_677 3_677 ?
N2 Cu1 N6 91.11(15) . 3_677 ?
N2 Cu1 N6 91.11(15) 3_677 . ?
N2 Cu1 N6 88.89(15) . . ?
N6 Cu1 N6 180.000(1) 3_677 . ?
N2 Cu1 N7 89.94(14) 3_677 2_556 ?
N2 Cu1 N7 90.06(14) . 2_556 ?
N6 Cu1 N7 89.69(15) 3_677 2_556 ?
N6 Cu1 N7 90.31(15) . 2_556 ?
N2 Cu1 N7 90.06(14) 3_677 4_676 ?
N2 Cu1 N7 89.94(14) . 4_676 ?
N6 Cu1 N7 90.31(15) 3_677 4_676 ?
N6 Cu1 N7 89.69(15) . 4_676 ?
N7 Cu1 N7 180.000(1) 2_556 4_676 ?
C1 N1 C3 107.4(4) . . ?
C1 N1 C4 125.9(5) . . ?
C3 N1 C4 126.7(4) . . ?
C1 N2 C2 106.0(4) . . ?
C1 N2 Cu1 127.9(3) . . ?
C2 N2 Cu1 126.1(3) . . ?
C5 N3 N4 107.4(4) . . ?
C5 N3 B1 132.1(4) . . ?
N4 N3 B1 120.5(4) . . ?
N5 N4 N3 107.5(3) . . ?
N4 N5 N6 109.7(3) . . ?
C5 N6 N5 106.2(3) . . ?
C5 N6 Cu1 128.8(3) . . ?
N5 N6 Cu1 124.9(3) . . ?
C6 N7 Cu1 159.7(4) . 2_546 ?
N3 B1 C6 108.1(4) . . ?
N3 B1 H1A 110.1 . . ?
C6 B1 H1A 110.1 . . ?
N3 B1 H1B 110.1 . . ?
C6 B1 H1B 110.1 . . ?
H1A B1 H1B 108.4 . . ?
N2 C1 N1 111.1(4) . . ?
N2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C3 C2 N2 108.7(5) . . ?
C3 C2 H2 125.6 . . ?
N2 C2 H2 125.6 . . ?
C2 C3 N1 106.9(4) . . ?
C2 C3 H3 126.6 . . ?
N1 C3 H3 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N6 C5 N3 109.1(4) . . ?
N6 C5 H5 125.4 . . ?
N3 C5 H5 125.4 . . ?
N7 C6 B1 177.8(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
N2 Cu1 N2 C1 79(100) 3_677 . . . ?
N6 Cu1 N2 C1 51.9(4) 3_677 . . . ?
N6 Cu1 N2 C1 -128.1(4) . . . . ?
N7 Cu1 N2 C1 -37.8(4) 2_556 . . . ?
N7 Cu1 N2 C1 142.2(4) 4_676 . . . ?
N2 Cu1 N2 C2 -98(100) 3_677 . . . ?
N6 Cu1 N2 C2 -125.3(4) 3_677 . . . ?
N6 Cu1 N2 C2 54.7(4) . . . . ?
N7 Cu1 N2 C2 145.0(4) 2_556 . . . ?
N7 Cu1 N2 C2 -35.0(4) 4_676 . . . ?
C5 N3 N4 N5 -0.6(5) . . . . ?
B1 N3 N4 N5 -178.5(4) . . . . ?
N3 N4 N5 N6 0.1(5) . . . . ?
N4 N5 N6 C5 0.4(5) . . . . ?
N4 N5 N6 Cu1 179.3(3) . . . . ?
N2 Cu1 N6 C5 -112.6(4) 3_677 . . . ?
N2 Cu1 N6 C5 67.4(4) . . . . ?
N6 Cu1 N6 C5 69(28) 3_677 . . . ?
N7 Cu1 N6 C5 -22.7(4) 2_556 . . . ?
N7 Cu1 N6 C5 157.3(4) 4_676 . . . ?
N2 Cu1 N6 N5 68.6(3) 3_677 . . . ?
N2 Cu1 N6 N5 -111.4(3) . . . . ?
N6 Cu1 N6 N5 -110(27) 3_677 . . . ?
N7 Cu1 N6 N5 158.6(3) 2_556 . . . ?
N7 Cu1 N6 N5 -21.4(3) 4_676 . . . ?
C5 N3 B1 C6 28.6(7) . . . . ?
N4 N3 B1 C6 -154.2(4) . . . . ?
C2 N2 C1 N1 0.7(6) . . . . ?
Cu1 N2 C1 N1 -176.9(3) . . . . ?
C3 N1 C1 N2 -0.8(6) . . . . ?
C4 N1 C1 N2 178.2(5) . . . . ?
C1 N2 C2 C3 -0.3(6) . . . . ?
Cu1 N2 C2 C3 177.3(3) . . . . ?
N2 C2 C3 N1 -0.1(6) . . . . ?
C1 N1 C3 C2 0.5(6) . . . . ?
C4 N1 C3 C2 -178.4(5) . . . . ?
N5 N6 C5 N3 -0.8(5) . . . . ?
Cu1 N6 C5 N3 -179.7(3) . . . . ?
N4 N3 C5 N6 0.9(5) . . . . ?
B1 N3 C5 N6 178.3(5) . . . . ?
Cu1 N7 C6 B1 122(14) 2_546 . . . ?
N3 B1 C6 N7 -164(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.352
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_210521a
_database_code_depnum_ccdc_archive 'CCDC 2087483'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 B6 Cu3 N30'
_chemical_formula_weight         838.04

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   21.194(2)
_cell_length_b                   8.5850(8)
_cell_length_c                   9.0509(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.100(2)
_cell_angle_gamma                90.00
_cell_volume                     1637.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1247
_cell_measurement_theta_min      3.487
_cell_measurement_theta_max      27.488

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             834
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8106
_exptl_absorpt_correction_T_max  0.9069
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2873
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1680
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2873
_reflns_number_gt                1017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0742P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     223
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.2060
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2289
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.5000 0.0289(8) Uani 1 2 d S . .
Cu2 Cu 0.33344(11) 0.4997(3) 0.1667(3) 0.0360(5) Uani 1 1 d . . .
N1 N 0.0738(6) 0.6188(18) 0.1119(18) 0.039(4) Uani 1 1 d . . .
N2 N 0.0292(6) 0.7293(19) 0.1117(15) 0.043(4) Uani 1 1 d . . .
N3 N -0.0013(5) 0.7028(17) 0.2304(15) 0.036(4) Uani 1 1 d . . .
N4 N 0.0241(5) 0.5731(15) 0.3011(15) 0.023(3) Uani 1 1 d U . .
N5 N 0.2430(5) 0.5656(18) 0.1109(17) 0.038(4) Uani 1 1 d . . .
N6 N 0.2600(6) 0.3811(16) 0.5576(19) 0.034(4) Uani 1 1 d . . .
N7 N 0.3044(5) 0.2691(17) 0.5479(16) 0.035(4) Uani 1 1 d . . .
N8 N 0.3337(7) 0.2988(16) 0.4330(14) 0.039(4) Uani 1 1 d . . .
N9 N 0.3082(5) 0.4307(17) 0.3692(14) 0.030(3) Uani 1 1 d . . .
N10 N 0.0882(5) 0.4272(17) 0.5604(16) 0.032(4) Uani 1 1 d . . .
N11 N 0.5886(6) 0.3828(18) 0.2275(16) 0.034(4) Uani 1 1 d . . .
N12 N 0.6353(7) 0.2683(19) 0.2141(16) 0.047(4) Uani 1 1 d . . .
N13 N 0.6667(7) 0.3014(19) 0.100(2) 0.060(5) Uani 1 1 d . . .
N14 N 0.6418(7) 0.4341(19) 0.025(2) 0.047(4) Uani 1 1 d U . .
N15 N 0.4234(8) 0.4348(19) 0.2257(17) 0.055(5) Uani 1 1 d . . .
B1 B 0.1223(9) 0.599(3) -0.014(3) 0.054(7) Uani 1 1 d U . .
H1A H 0.1121 0.5044 -0.0701 0.064 Uiso 1 1 calc R . .
H1B H 0.1176 0.6863 -0.0819 0.064 Uiso 1 1 calc R . .
B2 B 0.2099(9) 0.375(3) 0.675(2) 0.043(5) Uani 1 1 d U . .
H2A H 0.2221 0.4489 0.7538 0.051 Uiso 1 1 calc R . .
H2B H 0.2107 0.2716 0.7192 0.051 Uiso 1 1 calc R . .
B3 B 0.5465(8) 0.388(4) 0.353(2) 0.067(9) Uani 1 1 d . . .
H3A H 0.5584 0.4743 0.4196 0.080 Uiso 1 1 calc R . .
H3B H 0.5499 0.2919 0.4096 0.080 Uiso 1 1 calc R . .
C1 C 0.0721(5) 0.5212(13) 0.2241(13) 0.032(4) Uani 1 1 d G . .
H1 H 0.0980 0.4351 0.2462 0.039 Uiso 1 1 calc R . .
C2 C 0.1927(4) 0.5907(13) 0.0604(12) 0.031(4) Uani 1 1 d G . .
C3 C 0.2642(3) 0.4787(10) 0.4446(9) 0.042(5) Uani 1 1 d G . .
H3 H 0.2394 0.5669 0.4240 0.051 Uiso 1 1 calc R . .
C4 C 0.1396(4) 0.4124(14) 0.6048(12) 0.039(5) Uani 1 1 d G . .
C5 C 0.5948(5) 0.4783(13) 0.1105(12) 0.039(5) Uani 1 1 d GU . .
H5 H 0.5695 0.5658 0.0897 0.046 Uiso 1 1 calc R . .
C6 C 0.4780(4) 0.4102(10) 0.2756(9) 0.046(5) Uani 1 1 d G . .


_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 N10 1.991(12) . ?
Cu1 N10 1.991(12) 3_566 ?
Cu1 N4 2.023(13) 3_566 ?
Cu1 N4 2.023(13) . ?
Cu2 N14 1.954(18) 3_665 ?
Cu2 N15 2.003(18) . ?
Cu2 N5 2.011(11) . ?
Cu2 N9 2.050(13) . ?
N1 C1 1.321(19) . ?
N1 N2 1.339(17) . ?
N1 B1 1.62(2) . ?
N2 N3 1.331(17) . ?
N3 N4 1.366(17) . ?
N4 C1 1.367(15) . ?
N5 C2 1.135(13) . ?
N6 C3 1.332(17) . ?
N6 N7 1.356(17) . ?
N6 B2 1.58(2) . ?
N7 N8 1.291(18) . ?
N8 N9 1.357(18) . ?
N9 C3 1.281(15) . ?
N10 C4 1.128(15) . ?
N11 C5 1.356(17) . ?
N11 N12 1.41(2) . ?
N11 B3 1.52(2) . ?
N12 N13 1.318(19) . ?
N13 N14 1.40(2) . ?
N14 C5 1.376(18) . ?
N14 Cu2 1.954(18) 3_665 ?
N15 C6 1.215(18) . ?
B1 C2 1.57(2) . ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
B2 C4 1.59(2) . ?
B2 H2A 0.9700 . ?
B2 H2B 0.9700 . ?
B3 C6 1.557(16) . ?
B3 H3A 0.9700 . ?
B3 H3B 0.9700 . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 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
N10 Cu1 N10 180.000(1) . 3_566 ?
N10 Cu1 N4 88.6(5) . 3_566 ?
N10 Cu1 N4 91.4(5) 3_566 3_566 ?
N10 Cu1 N4 91.4(5) . . ?
N10 Cu1 N4 88.6(5) 3_566 . ?
N4 Cu1 N4 180.000(1) 3_566 . ?
N14 Cu2 N15 88.8(6) 3_665 . ?
N14 Cu2 N5 91.9(6) 3_665 . ?
N15 Cu2 N5 179.1(8) . . ?
N14 Cu2 N9 179.5(6) 3_665 . ?
N15 Cu2 N9 90.7(6) . . ?
N5 Cu2 N9 88.5(5) . . ?
C1 N1 N2 111.9(13) . . ?
C1 N1 B1 123.0(14) . . ?
N2 N1 B1 125.0(15) . . ?
N3 N2 N1 106.4(13) . . ?
N2 N3 N4 108.4(12) . . ?
N3 N4 C1 107.7(11) . . ?
N3 N4 Cu1 123.1(10) . . ?
C1 N4 Cu1 128.6(9) . . ?
C2 N5 Cu2 169.8(14) . . ?
C3 N6 N7 107.0(13) . . ?
C3 N6 B2 130.0(13) . . ?
N7 N6 B2 122.7(14) . . ?
N8 N7 N6 108.0(14) . . ?
N7 N8 N9 107.8(13) . . ?
C3 N9 N8 108.7(12) . . ?
C3 N9 Cu2 131.1(10) . . ?
N8 N9 Cu2 119.5(10) . . ?
C4 N10 Cu1 167.5(13) . . ?
C5 N11 N12 103.2(12) . . ?
C5 N11 B3 132.8(16) . . ?
N12 N11 B3 124.0(16) . . ?
N13 N12 N11 109.6(15) . . ?
N12 N13 N14 110.9(13) . . ?
C5 N14 N13 102.3(14) . . ?
C5 N14 Cu2 134.2(12) . 3_665 ?
N13 N14 Cu2 122.9(11) . 3_665 ?
C6 N15 Cu2 171.5(13) . . ?
C2 B1 N1 110.4(15) . . ?
C2 B1 H1A 109.6 . . ?
N1 B1 H1A 109.6 . . ?
C2 B1 H1B 109.6 . . ?
N1 B1 H1B 109.6 . . ?
H1A B1 H1B 108.1 . . ?
N6 B2 C4 113.1(14) . . ?
N6 B2 H2A 109.0 . . ?
C4 B2 H2A 109.0 . . ?
N6 B2 H2B 109.0 . . ?
C4 B2 H2B 109.0 . . ?
H2A B2 H2B 107.8 . . ?
N11 B3 C6 105.1(12) . . ?
N11 B3 H3A 110.7 . . ?
C6 B3 H3A 110.7 . . ?
N11 B3 H3B 110.7 . . ?
C6 B3 H3B 110.7 . . ?
H3A B3 H3B 108.8 . . ?
N1 C1 N4 105.6(11) . . ?
N1 C1 H1 127.2 . . ?
N4 C1 H1 127.2 . . ?
N5 C2 B1 171.5(16) . . ?
N9 C3 N6 108.6(11) . . ?
N9 C3 H3 125.7 . . ?
N6 C3 H3 125.7 . . ?
N10 C4 B2 173.9(14) . . ?
N11 C5 N14 113.9(12) . . ?
N11 C5 H5 123.0 . . ?
N14 C5 H5 123.0 . . ?
N15 C6 B3 174.4(14) . . ?

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
C1 N1 N2 N3 1.3(18) . . . . ?
B1 N1 N2 N3 178.2(15) . . . . ?
N1 N2 N3 N4 -1.4(17) . . . . ?
N2 N3 N4 C1 1.0(15) . . . . ?
N2 N3 N4 Cu1 173.0(10) . . . . ?
N10 Cu1 N4 N3 -144.6(11) . . . . ?
N10 Cu1 N4 N3 35.4(11) 3_566 . . . ?
N4 Cu1 N4 N3 32(100) 3_566 . . . ?
N10 Cu1 N4 C1 25.6(12) . . . . ?
N10 Cu1 N4 C1 -154.4(12) 3_566 . . . ?
N4 Cu1 N4 C1 -157(100) 3_566 . . . ?
N14 Cu2 N5 C2 49(7) 3_665 . . . ?
N15 Cu2 N5 C2 -162(41) . . . . ?
N9 Cu2 N5 C2 -131(7) . . . . ?
C3 N6 N7 N8 -0.3(16) . . . . ?
B2 N6 N7 N8 173.6(14) . . . . ?
N6 N7 N8 N9 0.3(16) . . . . ?
N7 N8 N9 C3 -0.3(16) . . . . ?
N7 N8 N9 Cu2 -171.5(9) . . . . ?
N14 Cu2 N9 C3 120(83) 3_665 . . . ?
N15 Cu2 N9 C3 152.0(12) . . . . ?
N5 Cu2 N9 C3 -27.6(12) . . . . ?
N14 Cu2 N9 N8 -71(84) 3_665 . . . ?
N15 Cu2 N9 N8 -39.1(12) . . . . ?
N5 Cu2 N9 N8 141.4(12) . . . . ?
N10 Cu1 N10 C4 -173(100) 3_566 . . . ?
N4 Cu1 N10 C4 -89(6) 3_566 . . . ?
N4 Cu1 N10 C4 91(6) . . . . ?
C5 N11 N12 N13 2.1(17) . . . . ?
B3 N11 N12 N13 -175.6(16) . . . . ?
N11 N12 N13 N14 -2.9(18) . . . . ?
N12 N13 N14 C5 2.5(17) . . . . ?
N12 N13 N14 Cu2 -169.9(11) . . . 3_665 ?
N14 Cu2 N15 C6 117(8) 3_665 . . . ?
N5 Cu2 N15 C6 -33(51) . . . . ?
N9 Cu2 N15 C6 -63(8) . . . . ?
C1 N1 B1 C2 -56(2) . . . . ?
N2 N1 B1 C2 127.8(17) . . . . ?
C3 N6 B2 C4 39(2) . . . . ?
N7 N6 B2 C4 -133.7(15) . . . . ?
C5 N11 B3 C6 52(3) . . . . ?
N12 N11 B3 C6 -131.5(16) . . . . ?
N2 N1 C1 N4 -0.7(17) . . . . ?
B1 N1 C1 N4 -177.7(14) . . . . ?
N3 N4 C1 N1 -0.2(15) . . . . ?
Cu1 N4 C1 N1 -171.6(11) . . . . ?
Cu2 N5 C2 B1 50(13) . . . . ?
N1 B1 C2 N5 103(9) . . . . ?
N8 N9 C3 N6 0.1(15) . . . . ?
Cu2 N9 C3 N6 169.9(10) . . . . ?
N7 N6 C3 N9 0.1(15) . . . . ?
B2 N6 C3 N9 -173.2(15) . . . . ?
Cu1 N10 C4 B2 132(13) . . . . ?
N6 B2 C4 N10 128(13) . . . . ?
N12 N11 C5 N14 -0.5(16) . . . . ?
B3 N11 C5 N14 176.8(17) . . . . ?
N13 N14 C5 N11 -1.1(17) . . . . ?
Cu2 N14 C5 N11 169.9(12) 3_665 . . . ?
Cu2 N15 C6 B3 14(21) . . . . ?
N11 B3 C6 N15 -147(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.146
####################################################################### 
# 
# 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_201013b
_database_code_depnum_ccdc_archive 'CCDC 2059564'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 B2 Cu N14'
_chemical_formula_weight         471.62

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.5143(9)
_cell_length_b                   9.8449(8)
_cell_length_c                   11.0882(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.865(4)
_cell_angle_gamma                90.00
_cell_volume                     1023.89(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1352
_cell_measurement_theta_min      2.217
_cell_measurement_theta_max      27.621

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             486
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7333
_exptl_absorpt_correction_T_max  0.9170
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4779
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_av_sigmaI/netI    0.1149
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1796
_reflns_number_gt                1208
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.0000 0.0299(3) Uani 1 2 d S . .
N1 N 0.5194(5) -0.1409(5) 0.3557(4) 0.0324(11) Uani 1 1 d . . .
N2 N 0.4776(5) -0.0577(5) 0.1599(4) 0.0316(11) Uani 1 1 d . . .
N3 N 0.4426(4) 0.3910(5) 0.1046(4) 0.0274(11) Uani 1 1 d . . .
N4 N 0.3234(5) 0.3748(5) -0.0111(4) 0.0387(12) Uani 1 1 d . . .
N5 N 0.3272(5) 0.2557(5) -0.0581(4) 0.0388(12) Uani 1 1 d . . .
N6 N 0.4459(4) 0.1917(5) 0.0274(4) 0.0286(11) Uani 1 1 d . . .
N7 N 0.7488(5) 0.0484(5) 0.1443(5) 0.0396(12) Uani 1 1 d . . .
B1 B 0.4716(7) 0.5271(6) 0.1846(7) 0.0337(16) Uani 1 1 d . . .
H1A H 0.4164 0.5302 0.2348 0.040 Uiso 1 1 calc R . .
H1B H 0.4434 0.6032 0.1223 0.040 Uiso 1 1 calc R . .
C1 C 0.5715(6) -0.1131(6) 0.2701(5) 0.0339(14) Uani 1 1 d . . .
H1 H 0.6649 -0.1314 0.2871 0.041 Uiso 1 1 calc R . .
C2 C 0.3586(6) -0.0443(7) 0.1783(6) 0.0433(16) Uani 1 1 d . . .
H2 H 0.2735 -0.0050 0.1167 0.052 Uiso 1 1 calc R . .
C3 C 0.3821(6) -0.0958(7) 0.2972(6) 0.0455(17) Uani 1 1 d . . .
H3 H 0.3178 -0.1002 0.3334 0.055 Uiso 1 1 calc R . .
C4 C 0.5976(6) -0.1962(7) 0.4900(5) 0.0450(17) Uani 1 1 d . . .
H4A H 0.6726 -0.2547 0.4916 0.054 Uiso 1 1 calc R . .
H4B H 0.6426 -0.1223 0.5528 0.054 Uiso 1 1 calc R . .
C5 C 0.5103(8) -0.2732(11) 0.5358(8) 0.097(3) Uani 1 1 d . . .
H5A H 0.4468 -0.2128 0.5502 0.145 Uiso 1 1 calc R . .
H5B H 0.5704 -0.3186 0.6189 0.145 Uiso 1 1 calc R . .
H5C H 0.4557 -0.3393 0.4685 0.145 Uiso 1 1 calc R . .
C6 C 0.5151(5) 0.2767(5) 0.1254(5) 0.0291(13) Uani 1 1 d . . .
H6 H 0.6027 0.2595 0.1991 0.035 Uiso 1 1 calc R . .
C7 C 0.8658(6) 0.0366(5) 0.2160(5) 0.0301(13) 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
Cu1 N2 1.975(4) 3_655 ?
Cu1 N2 1.975(4) . ?
Cu1 N6 2.033(5) 3_655 ?
Cu1 N6 2.033(5) . ?
Cu1 N7 2.418(5) 3_655 ?
Cu1 N7 2.418(5) . ?
N1 C1 1.321(7) . ?
N1 C3 1.362(7) . ?
N1 C4 1.444(6) . ?
N2 C1 1.295(7) . ?
N2 C2 1.362(7) . ?
N3 C6 1.320(6) . ?
N3 N4 1.337(5) . ?
N3 B1 1.559(7) . ?
N4 N5 1.291(6) . ?
N5 N6 1.336(6) . ?
N6 C6 1.302(6) . ?
N7 C7 1.129(7) . ?
B1 C7 1.563(8) 2_655 ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
C1 H1 0.9300 . ?
C2 C3 1.327(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.448(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?
C7 B1 1.563(8) 2_645 ?

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 Cu1 N2 180.0(4) 3_655 . ?
N2 Cu1 N6 88.72(17) 3_655 3_655 ?
N2 Cu1 N6 91.28(17) . 3_655 ?
N2 Cu1 N6 91.28(17) 3_655 . ?
N2 Cu1 N6 88.72(17) . . ?
N6 Cu1 N6 180.0(3) 3_655 . ?
N2 Cu1 N7 89.70(16) 3_655 3_655 ?
N2 Cu1 N7 90.30(16) . 3_655 ?
N6 Cu1 N7 90.58(17) 3_655 3_655 ?
N6 Cu1 N7 89.42(17) . 3_655 ?
N2 Cu1 N7 90.30(16) 3_655 . ?
N2 Cu1 N7 89.70(16) . . ?
N6 Cu1 N7 89.42(17) 3_655 . ?
N6 Cu1 N7 90.58(17) . . ?
N7 Cu1 N7 180.0(3) 3_655 . ?
C1 N1 C3 106.6(4) . . ?
C1 N1 C4 126.2(5) . . ?
C3 N1 C4 127.0(5) . . ?
C1 N2 C2 105.1(5) . . ?
C1 N2 Cu1 128.2(4) . . ?
C2 N2 Cu1 126.7(4) . . ?
C6 N3 N4 106.4(4) . . ?
C6 N3 B1 133.2(5) . . ?
N4 N3 B1 120.4(4) . . ?
N5 N4 N3 108.0(4) . . ?
N4 N5 N6 109.3(4) . . ?
C6 N6 N5 106.2(5) . . ?
C6 N6 Cu1 129.3(4) . . ?
N5 N6 Cu1 124.5(3) . . ?
C7 N7 Cu1 162.6(4) . . ?
N3 B1 C7 108.9(4) . 2_655 ?
N3 B1 H1A 109.9 . . ?
C7 B1 H1A 109.9 2_655 . ?
N3 B1 H1B 109.9 . . ?
C7 B1 H1B 109.9 2_655 . ?
H1A B1 H1B 108.3 . . ?
N2 C1 N1 112.2(5) . . ?
N2 C1 H1 123.9 . . ?
N1 C1 H1 123.9 . . ?
C3 C2 N2 109.9(5) . . ?
C3 C2 H2 125.1 . . ?
N2 C2 H2 125.1 . . ?
C2 C3 N1 106.2(5) . . ?
C2 C3 H3 126.9 . . ?
N1 C3 H3 126.9 . . ?
C5 C4 N1 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
N1 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
N1 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C6 N3 110.0(5) . . ?
N6 C6 H6 125.0 . . ?
N3 C6 H6 125.0 . . ?
N7 C7 B1 177.5(5) . 2_645 ?

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
N2 Cu1 N2 C1 -140(100) 3_655 . . . ?
N6 Cu1 N2 C1 58.5(5) 3_655 . . . ?
N6 Cu1 N2 C1 -121.5(5) . . . . ?
N7 Cu1 N2 C1 149.1(5) 3_655 . . . ?
N7 Cu1 N2 C1 -30.9(5) . . . . ?
N2 Cu1 N2 C2 39(100) 3_655 . . . ?
N6 Cu1 N2 C2 -123.0(5) 3_655 . . . ?
N6 Cu1 N2 C2 57.0(5) . . . . ?
N7 Cu1 N2 C2 -32.4(5) 3_655 . . . ?
N7 Cu1 N2 C2 147.6(5) . . . . ?
C6 N3 N4 N5 -1.3(6) . . . . ?
B1 N3 N4 N5 178.4(5) . . . . ?
N3 N4 N5 N6 1.8(6) . . . . ?
N4 N5 N6 C6 -1.6(6) . . . . ?
N4 N5 N6 Cu1 179.2(3) . . . . ?
N2 Cu1 N6 C6 -112.9(4) 3_655 . . . ?
N2 Cu1 N6 C6 67.1(4) . . . . ?
N6 Cu1 N6 C6 107(100) 3_655 . . . ?
N7 Cu1 N6 C6 157.4(4) 3_655 . . . ?
N7 Cu1 N6 C6 -22.6(4) . . . . ?
N2 Cu1 N6 N5 66.1(4) 3_655 . . . ?
N2 Cu1 N6 N5 -113.9(4) . . . . ?
N6 Cu1 N6 N5 -73(100) 3_655 . . . ?
N7 Cu1 N6 N5 -23.6(4) 3_655 . . . ?
N7 Cu1 N6 N5 156.4(4) . . . . ?
N2 Cu1 N7 C7 -114.2(15) 3_655 . . . ?
N2 Cu1 N7 C7 65.8(15) . . . . ?
N6 Cu1 N7 C7 -25.4(15) 3_655 . . . ?
N6 Cu1 N7 C7 154.6(15) . . . . ?
N7 Cu1 N7 C7 148(100) 3_655 . . . ?
C6 N3 B1 C7 18.5(8) . . . 2_655 ?
N4 N3 B1 C7 -161.1(4) . . . 2_655 ?
C2 N2 C1 N1 2.4(7) . . . . ?
Cu1 N2 C1 N1 -178.9(4) . . . . ?
C3 N1 C1 N2 -1.9(7) . . . . ?
C4 N1 C1 N2 -176.6(5) . . . . ?
C1 N2 C2 C3 -1.9(7) . . . . ?
Cu1 N2 C2 C3 179.3(4) . . . . ?
N2 C2 C3 N1 0.8(8) . . . . ?
C1 N1 C3 C2 0.6(7) . . . . ?
C4 N1 C3 C2 175.2(6) . . . . ?
C1 N1 C4 C5 -152.8(7) . . . . ?
C3 N1 C4 C5 33.7(9) . . . . ?
N5 N6 C6 N3 0.8(6) . . . . ?
Cu1 N6 C6 N3 180.0(3) . . . . ?
N4 N3 C6 N6 0.3(6) . . . . ?
B1 N3 C6 N6 -179.3(5) . . . . ?
Cu1 N7 C7 B1 -174(12) . . . 2_645 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.573
_refine_diff_density_min         -1.443
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_201014a
_database_code_depnum_ccdc_archive 'CCDC 2059563'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 B2 Cu N14'
_chemical_formula_weight         495.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.9096(11)
_cell_length_b                   9.7192(9)
_cell_length_c                   11.5319(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.316(5)
_cell_angle_gamma                90.00
_cell_volume                     1131.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    918
_cell_measurement_theta_min      6.1380
_cell_measurement_theta_max      68.4860

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7316
_exptl_absorpt_correction_T_max  0.9363
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.1281
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1970
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.38
_diffrn_reflns_theta_max         66.01
_reflns_number_total             1970
_reflns_number_gt                1363
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.8586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1970
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.5000 0.0307(3) Uani 1 2 d S . .
N1 N 0.1919(5) 0.1289(5) 0.1781(4) 0.0363(11) Uani 1 1 d . . .
N2 N 0.3324(5) 0.0540(5) 0.3581(4) 0.0342(11) Uani 1 1 d . . .
N3 N 0.6481(4) 0.3964(5) 0.5882(4) 0.0330(11) Uani 1 1 d . . .
N4 N 0.6410(5) 0.3881(5) 0.4686(5) 0.0419(13) Uani 1 1 d . . .
N5 N 0.5944(5) 0.2675(5) 0.4258(4) 0.0395(12) Uani 1 1 d . . .
N6 N 0.5707(4) 0.1957(4) 0.5161(4) 0.0306(11) Uani 1 1 d . . .
N7 N 0.6046(5) 0.5496(6) 0.8498(5) 0.0436(13) Uani 1 1 d . . .
B1 B 0.7059(7) 0.5267(7) 0.6673(7) 0.0384(16) Uani 1 1 d . . .
H1A H 0.6824 0.6077 0.6142 0.046 Uiso 1 1 calc R . .
H1B H 0.8018 0.5204 0.7050 0.046 Uiso 1 1 calc R . .
C1 C 0.3192(6) 0.1048(6) 0.2484(5) 0.0337(13) Uani 1 1 d . . .
H1 H 0.3892 0.1218 0.2230 0.040 Uiso 1 1 calc R . .
C2 C 0.2073(6) 0.0432(7) 0.3558(6) 0.0481(17) Uani 1 1 d . . .
H2 H 0.1856 0.0084 0.4208 0.058 Uiso 1 1 calc R . .
C3 C 0.1196(6) 0.0900(8) 0.2464(6) 0.0497(18) Uani 1 1 d . . .
H3 H 0.0281 0.0950 0.2220 0.060 Uiso 1 1 calc R . .
C4 C 0.1400(6) 0.1794(8) 0.0482(6) 0.0516(18) Uani 1 1 d . . .
H4A H 0.2111 0.2243 0.0315 0.062 Uiso 1 1 calc R . .
H4B H 0.1102 0.1017 -0.0083 0.062 Uiso 1 1 calc R . .
C5 C 0.0297(7) 0.2768(8) 0.0225(7) 0.059(2) Uani 1 1 d . . .
H5 H 0.0437 0.3535 0.0741 0.071 Uiso 1 1 calc R . .
C6 C -0.0853(7) 0.2634(10) -0.0667(8) 0.076(3) Uani 1 1 d . . .
H6A H -0.1028 0.1879 -0.1201 0.091 Uiso 1 1 calc R . .
H6B H -0.1506 0.3292 -0.0774 0.091 Uiso 1 1 calc R . .
C7 C 0.6049(5) 0.2777(5) 0.6138(5) 0.0332(13) Uani 1 1 d . . .
H7 H 0.5994 0.2554 0.6901 0.040 Uiso 1 1 calc R . .
C8 C 0.6469(6) 0.5386(6) 0.7741(5) 0.0333(13) 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
Cu1 N2 2.006(5) 3_656 ?
Cu1 N2 2.006(5) . ?
Cu1 N6 2.034(4) 3_656 ?
Cu1 N6 2.034(4) . ?
Cu1 N7 2.457(5) 2_646 ?
Cu1 N7 2.457(5) 4_565 ?
N1 C1 1.337(7) . ?
N1 C3 1.362(7) . ?
N1 C4 1.471(7) . ?
N2 C1 1.314(7) . ?
N2 C2 1.360(7) . ?
N3 C7 1.322(7) . ?
N3 N4 1.353(6) . ?
N3 B1 1.548(8) . ?
N4 N5 1.298(7) . ?
N5 N6 1.357(6) . ?
N6 C7 1.313(7) . ?
N7 C8 1.137(7) . ?
N7 Cu1 2.457(5) 2_656 ?
B1 C8 1.595(9) . ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
C1 H1 0.9300 . ?
C2 C3 1.341(9) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.470(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.291(9) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C7 H7 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 Cu1 N2 180.000(1) 3_656 . ?
N2 Cu1 N6 91.50(18) 3_656 3_656 ?
N2 Cu1 N6 88.50(18) . 3_656 ?
N2 Cu1 N6 88.50(18) 3_656 . ?
N2 Cu1 N6 91.50(18) . . ?
N6 Cu1 N6 180.0 3_656 . ?
N2 Cu1 N7 90.00(18) 3_656 2_646 ?
N2 Cu1 N7 90.00(18) . 2_646 ?
N6 Cu1 N7 89.21(18) 3_656 2_646 ?
N6 Cu1 N7 90.79(18) . 2_646 ?
N2 Cu1 N7 90.00(18) 3_656 4_565 ?
N2 Cu1 N7 90.00(18) . 4_565 ?
N6 Cu1 N7 90.79(18) 3_656 4_565 ?
N6 Cu1 N7 89.21(18) . 4_565 ?
N7 Cu1 N7 180.0 2_646 4_565 ?
C1 N1 C3 107.3(5) . . ?
C1 N1 C4 125.8(5) . . ?
C3 N1 C4 126.7(5) . . ?
C1 N2 C2 105.6(5) . . ?
C1 N2 Cu1 128.1(4) . . ?
C2 N2 Cu1 126.4(4) . . ?
C7 N3 N4 106.8(5) . . ?
C7 N3 B1 133.0(5) . . ?
N4 N3 B1 120.2(5) . . ?
N5 N4 N3 107.7(5) . . ?
N4 N5 N6 109.5(4) . . ?
C7 N6 N5 105.8(4) . . ?
C7 N6 Cu1 128.3(4) . . ?
N5 N6 Cu1 125.9(4) . . ?
C8 N7 Cu1 162.8(5) . 2_656 ?
N3 B1 C8 108.7(5) . . ?
N3 B1 H1A 109.9 . . ?
C8 B1 H1A 109.9 . . ?
N3 B1 H1B 109.9 . . ?
C8 B1 H1B 109.9 . . ?
H1A B1 H1B 108.3 . . ?
N2 C1 N1 111.0(5) . . ?
N2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C3 C2 N2 110.1(6) . . ?
C3 C2 H2 124.9 . . ?
N2 C2 H2 124.9 . . ?
C2 C3 N1 106.0(5) . . ?
C2 C3 H3 127.0 . . ?
N1 C3 H3 127.0 . . ?
C5 C4 N1 112.9(5) . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
N1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 124.7(8) . . ?
C6 C5 H5 117.6 . . ?
C4 C5 H5 117.6 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N6 C7 N3 110.3(5) . . ?
N6 C7 H7 124.9 . . ?
N3 C7 H7 124.9 . . ?
N7 C8 B1 178.8(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
N2 Cu1 N2 C1 -52(100) 3_656 . . . ?
N6 Cu1 N2 C1 -118.9(5) 3_656 . . . ?
N6 Cu1 N2 C1 61.1(5) . . . . ?
N7 Cu1 N2 C1 151.9(5) 2_646 . . . ?
N7 Cu1 N2 C1 -28.1(5) 4_565 . . . ?
N2 Cu1 N2 C2 127(100) 3_656 . . . ?
N6 Cu1 N2 C2 60.1(5) 3_656 . . . ?
N6 Cu1 N2 C2 -119.9(5) . . . . ?
N7 Cu1 N2 C2 -29.2(5) 2_646 . . . ?
N7 Cu1 N2 C2 150.8(5) 4_565 . . . ?
C7 N3 N4 N5 0.1(7) . . . . ?
B1 N3 N4 N5 177.4(5) . . . . ?
N3 N4 N5 N6 -0.1(7) . . . . ?
N4 N5 N6 C7 0.0(6) . . . . ?
N4 N5 N6 Cu1 -179.0(4) . . . . ?
N2 Cu1 N6 C7 -59.5(5) 3_656 . . . ?
N2 Cu1 N6 C7 120.5(5) . . . . ?
N6 Cu1 N6 C7 -174(100) 3_656 . . . ?
N7 Cu1 N6 C7 30.5(5) 2_646 . . . ?
N7 Cu1 N6 C7 -149.5(5) 4_565 . . . ?
N2 Cu1 N6 N5 119.3(5) 3_656 . . . ?
N2 Cu1 N6 N5 -60.7(5) . . . . ?
N6 Cu1 N6 N5 5(35) 3_656 . . . ?
N7 Cu1 N6 N5 -150.8(4) 2_646 . . . ?
N7 Cu1 N6 N5 29.2(4) 4_565 . . . ?
C7 N3 B1 C8 -28.0(9) . . . . ?
N4 N3 B1 C8 155.5(5) . . . . ?
C2 N2 C1 N1 1.2(7) . . . . ?
Cu1 N2 C1 N1 -179.7(4) . . . . ?
C3 N1 C1 N2 -0.6(7) . . . . ?
C4 N1 C1 N2 -177.0(6) . . . . ?
C1 N2 C2 C3 -1.3(7) . . . . ?
Cu1 N2 C2 C3 179.5(5) . . . . ?
N2 C2 C3 N1 1.0(8) . . . . ?
C1 N1 C3 C2 -0.2(8) . . . . ?
C4 N1 C3 C2 176.1(6) . . . . ?
C1 N1 C4 C5 -142.2(6) . . . . ?
C3 N1 C4 C5 42.1(10) . . . . ?
N1 C4 C5 C6 -125.3(8) . . . . ?
N5 N6 C7 N3 0.1(6) . . . . ?
Cu1 N6 C7 N3 179.1(3) . . . . ?
N4 N3 C7 N6 -0.2(6) . . . . ?
B1 N3 C7 N6 -177.0(6) . . . . ?
Cu1 N7 C8 B1 158(27) 2_656 . . . ?
N3 B1 C8 N7 -138(28) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.116
####################################################################### 
# 
# 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_210602b
_database_code_depnum_ccdc_archive 'CCDC 2094480'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 B2 Cu N14'
_chemical_formula_weight         467.58

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.5342(12)
_cell_length_b                   9.6428(11)
_cell_length_c                   11.0538(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.872(4)
_cell_angle_gamma                90.00
_cell_volume                     1010.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2475
_cell_measurement_theta_min      2.225
_cell_measurement_theta_max      27.80

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    1.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4919
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1783
_reflns_number_gt                1488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.2433P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1783
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.0000 0.02616(19) Uani 1 2 d S . .
N1 N 0.5118(2) 0.6368(2) 0.3572(2) 0.0302(5) Uani 1 1 d . . .
N2 N 0.4741(2) 0.5569(2) 0.1598(2) 0.0271(5) Uani 1 1 d . . .
N3 N 0.4468(2) 0.1032(2) 0.1113(2) 0.0260(5) Uani 1 1 d . . .
N4 N 0.3287(2) 0.1158(3) -0.0042(2) 0.0370(6) Uani 1 1 d . . .
N5 N 0.3303(2) 0.2366(3) -0.0526(2) 0.0351(6) Uani 1 1 d . . .
N6 N 0.4476(2) 0.3044(2) 0.0291(2) 0.0267(5) Uani 1 1 d . . .
N7 N 0.7544(3) -0.0503(3) 0.3565(2) 0.0370(6) Uani 1 1 d . . .
B1 B 0.4753(4) -0.0317(4) 0.1973(4) 0.0341(8) Uani 1 1 d . . .
H1A H 0.4439 -0.1122 0.1390 0.041 Uiso 1 1 calc R . .
H1B H 0.4242 -0.0287 0.2520 0.041 Uiso 1 1 calc R . .
C1 C 0.5676(3) 0.6082(3) 0.2727(3) 0.0309(6) Uani 1 1 d . . .
H1 H 0.6617 0.6231 0.2918 0.037 Uiso 1 1 calc R . .
C2 C 0.3513(3) 0.5524(4) 0.1735(3) 0.0387(7) Uani 1 1 d . . .
H2 H 0.2652 0.5201 0.1088 0.046 Uiso 1 1 calc R . .
C3 C 0.3742(3) 0.6016(4) 0.2939(3) 0.0412(8) Uani 1 1 d . . .
H3 H 0.3079 0.6101 0.3279 0.049 Uiso 1 1 calc R . .
C4 C 0.5857(3) 0.6932(4) 0.4864(3) 0.0439(8) Uani 1 1 d D . .
H4 H 0.6827 0.7042 0.5185 0.053 Uiso 1 1 calc R . .
C5 C 0.5297(5) 0.7307(5) 0.5631(4) 0.0761(14) Uani 1 1 d D . .
H5A H 0.4330 0.7213 0.5344 0.091 Uiso 1 1 calc R . .
H5B H 0.5857 0.7673 0.6477 0.091 Uiso 1 1 calc R . .
C6 C 0.5166(3) 0.2196(3) 0.1284(3) 0.0283(6) Uani 1 1 d . . .
H6 H 0.6027 0.2391 0.2008 0.034 Uiso 1 1 calc R . .
C7 C 0.6379(3) -0.0413(3) 0.2894(3) 0.0281(6) 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
Cu1 N2 1.980(2) . ?
Cu1 N2 1.980(2) 3_665 ?
Cu1 N6 2.030(2) . ?
Cu1 N6 2.030(2) 3_665 ?
Cu1 N7 2.421(3) 2_655 ?
Cu1 N7 2.421(3) 4_565 ?
N1 C1 1.332(3) . ?
N1 C3 1.349(4) . ?
N1 C4 1.404(4) . ?
N2 C1 1.303(3) . ?
N2 C2 1.367(4) . ?
N3 C6 1.310(3) . ?
N3 N4 1.344(3) . ?
N3 B1 1.560(4) . ?
N4 N5 1.285(3) . ?
N5 N6 1.340(3) . ?
N6 C6 1.306(3) . ?
N7 C7 1.127(4) . ?
N7 Cu1 2.421(3) 2_645 ?
B1 C7 1.568(4) . ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
C1 H1 0.9300 . ?
C2 C3 1.332(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.278(4) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C6 H6 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 Cu1 N2 180.00(4) . 3_665 ?
N2 Cu1 N6 87.91(9) . . ?
N2 Cu1 N6 92.09(9) 3_665 . ?
N2 Cu1 N6 92.09(9) . 3_665 ?
N2 Cu1 N6 87.91(9) 3_665 3_665 ?
N6 Cu1 N6 180.0 . 3_665 ?
N2 Cu1 N7 89.70(9) . 2_655 ?
N2 Cu1 N7 90.30(9) 3_665 2_655 ?
N6 Cu1 N7 89.80(9) . 2_655 ?
N6 Cu1 N7 90.20(9) 3_665 2_655 ?
N2 Cu1 N7 90.30(9) . 4_565 ?
N2 Cu1 N7 89.70(9) 3_665 4_565 ?
N6 Cu1 N7 90.20(9) . 4_565 ?
N6 Cu1 N7 89.80(9) 3_665 4_565 ?
N7 Cu1 N7 180.0 2_655 4_565 ?
C1 N1 C3 106.7(2) . . ?
C1 N1 C4 125.1(3) . . ?
C3 N1 C4 128.2(2) . . ?
C1 N2 C2 105.2(2) . . ?
C1 N2 Cu1 128.21(19) . . ?
C2 N2 Cu1 126.56(19) . . ?
C6 N3 N4 106.7(2) . . ?
C6 N3 B1 132.8(2) . . ?
N4 N3 B1 120.4(2) . . ?
N5 N4 N3 107.7(2) . . ?
N4 N5 N6 109.7(2) . . ?
C6 N6 N5 105.8(2) . . ?
C6 N6 Cu1 128.68(19) . . ?
N5 N6 Cu1 125.50(17) . . ?
C7 N7 Cu1 164.0(3) . 2_645 ?
N3 B1 C7 108.1(2) . . ?
N3 B1 H1A 110.1 . . ?
C7 B1 H1A 110.1 . . ?
N3 B1 H1B 110.1 . . ?
C7 B1 H1B 110.1 . . ?
H1A B1 H1B 108.4 . . ?
N2 C1 N1 111.7(2) . . ?
N2 C1 H1 124.2 . . ?
N1 C1 H1 124.2 . . ?
C3 C2 N2 109.4(3) . . ?
C3 C2 H2 125.3 . . ?
N2 C2 H2 125.3 . . ?
C2 C3 N1 107.0(3) . . ?
C2 C3 H3 126.5 . . ?
N1 C3 H3 126.5 . . ?
C5 C4 N1 124.9(3) . . ?
C5 C4 H4 117.5 . . ?
N1 C4 H4 117.5 . . ?
C4 C5 H5A 120.0 . . ?
C4 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
N6 C6 N3 110.1(2) . . ?
N6 C6 H6 124.9 . . ?
N3 C6 H6 124.9 . . ?
N7 C7 B1 178.9(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
N2 Cu1 N2 C1 -56(100) 3_665 . . . ?
N6 Cu1 N2 C1 117.9(3) . . . . ?
N6 Cu1 N2 C1 -62.1(3) 3_665 . . . ?
N7 Cu1 N2 C1 28.1(3) 2_655 . . . ?
N7 Cu1 N2 C1 -151.9(3) 4_565 . . . ?
N2 Cu1 N2 C2 123(100) 3_665 . . . ?
N6 Cu1 N2 C2 -63.3(3) . . . . ?
N6 Cu1 N2 C2 116.7(3) 3_665 . . . ?
N7 Cu1 N2 C2 -153.1(3) 2_655 . . . ?
N7 Cu1 N2 C2 26.9(3) 4_565 . . . ?
C6 N3 N4 N5 0.0(3) . . . . ?
B1 N3 N4 N5 178.6(2) . . . . ?
N3 N4 N5 N6 0.0(3) . . . . ?
N4 N5 N6 C6 0.0(3) . . . . ?
N4 N5 N6 Cu1 -179.18(18) . . . . ?
N2 Cu1 N6 C6 -66.5(2) . . . . ?
N2 Cu1 N6 C6 113.5(2) 3_665 . . . ?
N6 Cu1 N6 C6 142(100) 3_665 . . . ?
N7 Cu1 N6 C6 23.2(2) 2_655 . . . ?
N7 Cu1 N6 C6 -156.8(2) 4_565 . . . ?
N2 Cu1 N6 N5 112.6(2) . . . . ?
N2 Cu1 N6 N5 -67.4(2) 3_665 . . . ?
N6 Cu1 N6 N5 -39(100) 3_665 . . . ?
N7 Cu1 N6 N5 -157.7(2) 2_655 . . . ?
N7 Cu1 N6 N5 22.3(2) 4_565 . . . ?
C6 N3 B1 C7 -23.5(4) . . . . ?
N4 N3 B1 C7 158.2(2) . . . . ?
C2 N2 C1 N1 -0.1(3) . . . . ?
Cu1 N2 C1 N1 178.94(18) . . . . ?
C3 N1 C1 N2 -0.1(3) . . . . ?
C4 N1 C1 N2 -179.8(3) . . . . ?
C1 N2 C2 C3 0.2(4) . . . . ?
Cu1 N2 C2 C3 -178.8(2) . . . . ?
N2 C2 C3 N1 -0.3(4) . . . . ?
C1 N1 C3 C2 0.3(4) . . . . ?
C4 N1 C3 C2 180.0(3) . . . . ?
C1 N1 C4 C5 174.1(4) . . . . ?
C3 N1 C4 C5 -5.5(6) . . . . ?
N5 N6 C6 N3 0.0(3) . . . . ?
Cu1 N6 C6 N3 179.14(17) . . . . ?
N4 N3 C6 N6 0.0(3) . . . . ?
B1 N3 C6 N6 -178.4(3) . . . . ?
Cu1 N7 C7 B1 -149(16) 2_645 . . . ?
N3 B1 C7 N7 -178(100) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_exp_7377
_database_code_depnum_ccdc_archive 'CCDC 2111636'
loop_
_audit_author_name
_audit_author_address
'Yiqiang Xu'
;Beijing Institute of Technology 
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-07-09
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C12 H16 Cu0.5 N4), 2(N O3)'
_chemical_formula_sum            'C24 H32 Cu N10 O6'
_chemical_formula_weight         620.14
_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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8723(11)
_cell_length_b                   8.9291(10)
_cell_length_c                   9.0178(12)
_cell_angle_alpha                105.573(11)
_cell_angle_beta                 98.354(11)
_cell_angle_gamma                94.530(10)
_cell_volume                     675.64(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1575
_cell_measurement_temperature    113.40(10)
_cell_measurement_theta_max      27.0570
_cell_measurement_theta_min      3.7590
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             323
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4305
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.54
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.40(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.5095
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   25.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega   46.00   89.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       16.0852 -178.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   35.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   77.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   81.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   65.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000    0.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0603894000
_diffrn_orient_matrix_UB_12      -0.0457147000
_diffrn_orient_matrix_UB_13      0.0104455000
_diffrn_orient_matrix_UB_21      0.0399954000
_diffrn_orient_matrix_UB_22      0.0333141000
_diffrn_orient_matrix_UB_23      -0.0484242000
_diffrn_orient_matrix_UB_31      0.0372380000
_diffrn_orient_matrix_UB_32      0.0608507000
_diffrn_orient_matrix_UB_33      0.0664624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2271
_reflns_number_total             2570
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.1293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.5000 0.01134(15) Uani 1 2 d S . .
N3 N 0.1957(3) 0.5514(2) 0.4295(2) 0.0117(5) Uani 1 1 d . . .
N4 N 0.4082(3) 0.5133(2) 0.3333(2) 0.0109(5) Uani 1 1 d . . .
N1 N -0.0795(3) 0.3693(2) 0.2797(2) 0.0108(5) Uani 1 1 d . . .
N2 N -0.1463(3) 0.1784(2) 0.0605(2) 0.0124(5) Uani 1 1 d . . .
C2 C -0.0865(3) 0.4325(3) 0.1550(3) 0.0121(6) Uani 1 1 d . . .
H2 H -0.0662 0.5382 0.1624 0.015 Uiso 1 1 calc R . .
C8 C 0.2632(3) 0.6921(3) 0.4197(3) 0.0139(6) Uani 1 1 d . . .
H8 H 0.2244 0.7874 0.4492 0.017 Uiso 1 1 calc R . .
C10 C 0.5277(3) 0.4319(3) 0.2602(3) 0.0151(6) Uani 1 1 d . . .
H10A H 0.5574 0.3545 0.3128 0.018 Uiso 1 1 calc R . .
H10B H 0.6174 0.5070 0.2738 0.018 Uiso 1 1 calc R . .
C7 C 0.2874(3) 0.4458(3) 0.3751(3) 0.0110(6) Uani 1 1 d . . .
H7 H 0.2697 0.3397 0.3672 0.013 Uiso 1 1 calc R . .
C5 C -0.3473(4) 0.0061(3) -0.1422(3) 0.0181(6) Uani 1 1 d . . .
H5 H -0.4287 0.0238 -0.0879 0.022 Uiso 1 1 calc R . .
C9 C 0.3944(3) 0.6710(3) 0.3609(3) 0.0151(6) Uani 1 1 d . . .
H9 H 0.4614 0.7470 0.3428 0.018 Uiso 1 1 calc R . .
C3 C -0.1278(3) 0.3148(3) 0.0199(3) 0.0146(6) Uani 1 1 d . . .
H3 H -0.1410 0.3250 -0.0810 0.017 Uiso 1 1 calc R . .
C1 C -0.1167(3) 0.2153(3) 0.2192(3) 0.0137(6) Uani 1 1 d . . .
H1 H -0.1218 0.1436 0.2769 0.016 Uiso 1 1 calc R . .
C12 C 0.3374(4) 0.3353(3) 0.0091(3) 0.0202(7) Uani 1 1 d . . .
H12A H 0.2584 0.3754 0.0587 0.024 Uiso 1 1 calc R . .
H12B H 0.3178 0.2834 -0.0973 0.024 Uiso 1 1 calc R . .
C11 C 0.4763(3) 0.3519(3) 0.0889(3) 0.0160(6) Uani 1 1 d . . .
H11 H 0.5510 0.3096 0.0336 0.019 Uiso 1 1 calc R . .
C6 C -0.3782(4) -0.0296(3) -0.2959(3) 0.0225(7) Uani 1 1 d . . .
H6A H -0.2995 -0.0480 -0.3538 0.027 Uiso 1 1 calc R . .
H6B H -0.4787 -0.0365 -0.3464 0.027 Uiso 1 1 calc R . .
C4 C -0.1908(4) 0.0203(3) -0.0492(3) 0.0183(6) Uani 1 1 d . . .
H4A H -0.1890 -0.0567 0.0090 0.022 Uiso 1 1 calc R . .
H4B H -0.1171 -0.0014 -0.1194 0.022 Uiso 1 1 calc R . .
O1 O 0.1178(3) 0.2557(2) 0.5490(2) 0.0253(5) Uani 1 1 d . . .
N5 N 0.1267(3) 0.1615(3) 0.6305(2) 0.0146(5) Uani 1 1 d . . .
O3 O 0.2365(3) 0.0818(2) 0.6307(2) 0.0273(5) Uani 1 1 d . . .
O2 O 0.0284(3) 0.1500(3) 0.7145(2) 0.0273(5) 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
Cu1 N3 1.995(2) 2_566 ?
Cu1 N3 1.995(2) . ?
Cu1 N1 2.006(2) . ?
Cu1 N1 2.006(2) 2_566 ?
N3 C8 1.379(3) . ?
N3 C7 1.334(3) . ?
N4 C10 1.468(3) . ?
N4 C7 1.338(3) . ?
N4 C9 1.381(3) . ?
N1 C2 1.383(3) . ?
N1 C1 1.330(3) . ?
N2 C3 1.367(3) . ?
N2 C1 1.360(3) . ?
N2 C4 1.475(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.353(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(3) . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.318(4) . ?
C5 C4 1.491(4) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C12 C11 1.309(4) . ?
C11 H11 0.9300 . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O1 N5 1.257(3) . ?
N5 O3 1.251(3) . ?
N5 O2 1.251(3) . ?

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 180.00(6) . 2_566 ?
N3 Cu1 N1 87.59(9) . . ?
N3 Cu1 N1 92.41(9) 2_566 . ?
N3 Cu1 N1 92.41(9) . 2_566 ?
N3 Cu1 N1 87.59(9) 2_566 2_566 ?
N1 Cu1 N1 180.0 2_566 . ?
C8 N3 Cu1 130.38(17) . . ?
C7 N3 Cu1 124.03(19) . . ?
C7 N3 C8 105.6(2) . . ?
C7 N4 C10 125.9(2) . . ?
C7 N4 C9 107.8(2) . . ?
C9 N4 C10 126.1(2) . . ?
C2 N1 Cu1 121.76(17) . . ?
C1 N1 Cu1 131.25(18) . . ?
C1 N1 C2 106.6(2) . . ?
C3 N2 C4 125.8(2) . . ?
C1 N2 C3 107.7(2) . . ?
C1 N2 C4 126.6(2) . . ?
N1 C2 H2 125.6 . . ?
C3 C2 N1 108.9(2) . . ?
C3 C2 H2 125.6 . . ?
N3 C8 H8 125.0 . . ?
C9 C8 N3 109.9(2) . . ?
C9 C8 H8 125.0 . . ?
N4 C10 H10A 109.0 . . ?
N4 C10 H10B 109.0 . . ?
N4 C10 C11 112.8(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N3 C7 N4 110.8(2) . . ?
N3 C7 H7 124.6 . . ?
N4 C7 H7 124.6 . . ?
C6 C5 H5 117.7 . . ?
C6 C5 C4 124.5(3) . . ?
C4 C5 H5 117.7 . . ?
N4 C9 H9 127.1 . . ?
C8 C9 N4 105.8(2) . . ?
C8 C9 H9 127.1 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 106.9(2) . . ?
C2 C3 H3 126.5 . . ?
N1 C1 N2 110.0(2) . . ?
N1 C1 H1 125.0 . . ?
N2 C1 H1 125.0 . . ?
H12A C12 H12B 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
C10 C11 H11 116.5 . . ?
C12 C11 C10 126.9(2) . . ?
C12 C11 H11 116.5 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N2 C4 C5 111.3(2) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O3 N5 O1 119.9(2) . . ?
O2 N5 O1 120.3(2) . . ?
O2 N5 O3 119.9(2) . . ?

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 C8 C9 -178.26(17) . . . . ?
Cu1 N3 C7 N4 178.53(15) . . . . ?
Cu1 N1 C2 C3 173.09(17) . . . . ?
Cu1 N1 C1 N2 -172.01(17) . . . . ?
N3 Cu1 N3 C8 69(100) 2_566 . . . ?
N3 Cu1 N3 C7 -109(100) 2_566 . . . ?
N3 Cu1 N1 C2 -58.0(2) . . . . ?
N3 Cu1 N1 C2 122.0(2) 2_566 . . . ?
N3 Cu1 N1 C1 113.4(2) . . . . ?
N3 Cu1 N1 C1 -66.6(2) 2_566 . . . ?
N3 C8 C9 N4 0.1(3) . . . . ?
N4 C10 C11 C12 -7.8(4) . . . . ?
N1 Cu1 N3 C8 -65.9(2) 2_566 . . . ?
N1 Cu1 N3 C8 114.1(2) . . . . ?
N1 Cu1 N3 C7 -63.5(2) . . . . ?
N1 Cu1 N3 C7 116.5(2) 2_566 . . . ?
N1 Cu1 N1 C2 -8(100) 2_566 . . . ?
N1 Cu1 N1 C1 163(100) 2_566 . . . ?
N1 C2 C3 N2 -0.1(3) . . . . ?
C2 N1 C1 N2 0.3(3) . . . . ?
C8 N3 C7 N4 0.5(3) . . . . ?
C10 N4 C7 N3 -176.1(2) . . . . ?
C10 N4 C9 C8 175.9(2) . . . . ?
C7 N3 C8 C9 -0.4(3) . . . . ?
C7 N4 C10 C11 77.7(3) . . . . ?
C7 N4 C9 C8 0.2(3) . . . . ?
C9 N4 C10 C11 -97.3(3) . . . . ?
C9 N4 C7 N3 -0.4(3) . . . . ?
C3 N2 C1 N1 -0.4(3) . . . . ?
C3 N2 C4 C5 -63.0(3) . . . . ?
C1 N1 C2 C3 -0.1(3) . . . . ?
C1 N2 C3 C2 0.3(3) . . . . ?
C1 N2 C4 C5 116.8(3) . . . . ?
C6 C5 C4 N2 120.7(3) . . . . ?
C4 N2 C3 C2 -179.9(2) . . . . ?
C4 N2 C1 N1 179.8(2) . . . . ?
