# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Cpd1
_database_code_depnum_ccdc_archive 'CCDC 2222617'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 Cl2 Cu N6 O8'
_chemical_formula_weight         480.71

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.9429(8)
_cell_length_b                   6.0099(3)
_cell_length_c                   18.4308(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.165(3)
_cell_angle_gamma                90
_cell_volume                     1763.26(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5126
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.596
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12158
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2275
_reflns_number_gt                2096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+4.6253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.000000 1.000000 0.500000 0.02223(11) Uani 1 2 d S . P . .
O1 O 1.11759(10) 0.7947(3) 0.57531(8) 0.0330(4) Uani 1 1 d . . . . .
N3 N 0.98240(12) 1.1913(3) 0.58464(10) 0.0245(4) Uani 1 1 d . . . . .
C5 C 0.90426(15) 1.2343(4) 0.69601(12) 0.0302(5) Uani 1 1 d . . . . .
H5A H 0.936204 1.372453 0.703561 0.045 Uiso 1 1 calc R U . . .
H5B H 0.917928 1.131714 0.736272 0.045 Uiso 1 1 calc R U . . .
H5C H 0.843994 1.267549 0.694013 0.045 Uiso 1 1 calc R U . . .
C4 C 0.92636(13) 1.1304(4) 0.62683(11) 0.0232(4) Uani 1 1 d . . . . .
Cl1 Cl 1.11796(3) 0.70853(8) 0.64854(3) 0.02197(12) Uani 1 1 d . . . . .
N1 N 0.90616(11) 0.8380(3) 0.54195(9) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.88158(10) 0.9418(3) 0.60343(9) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.81690(13) 0.8285(4) 0.63197(12) 0.0288(5) Uani 1 1 d . . . . .
H3A H 0.789278 0.866608 0.674616 0.035 Uiso 1 1 calc R U . . .
C1 C 0.85682(14) 0.6635(4) 0.53267(12) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.859503 0.559795 0.493960 0.033 Uiso 1 1 calc R U . . .
C2 C 0.79944(14) 0.6516(4) 0.58812(13) 0.0321(5) Uani 1 1 d . . . . .
H2 H 0.757251 0.542185 0.593588 0.039 Uiso 1 1 calc R U . . .
O4 O 1.12204(12) 0.4682(3) 0.64544(10) 0.0394(4) Uani 1 1 d . . . . .
O2 O 1.04305(11) 0.7730(3) 0.68216(10) 0.0444(5) Uani 1 1 d . . . . .
O3 O 1.19008(12) 0.7889(4) 0.68967(10) 0.0446(5) Uani 1 1 d . . . . .
H3 H 1.0049(18) 1.298(5) 0.6002(15) 0.038(8) Uiso 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 1.9703(18) . ?
Cu1 N3 1.9704(18) 5_776 ?
Cu1 N1 1.9776(17) 5_776 ?
Cu1 N1 1.9777(17) . ?
Cu1 O1 2.5839(17) . ?
O1 Cl1 1.4454(16) . ?
N3 C4 1.270(3) . ?
N3 H3 0.78(3) . ?
C5 C4 1.480(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 N2 1.395(3) . ?
Cl1 O3 1.4261(18) . ?
Cl1 O2 1.4290(16) . ?
Cl1 O4 1.4473(17) . ?
N1 C1 1.317(3) . ?
N1 N2 1.369(2) . ?
N2 C3 1.365(3) . ?
C3 C2 1.355(3) . ?
C3 H3A 0.9500 . ?
C1 C2 1.411(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.00(11) . 5_776 ?
N3 Cu1 N1 99.57(7) . 5_776 ?
N3 Cu1 N1 80.43(7) 5_776 5_776 ?
N3 Cu1 N1 80.43(7) . . ?
N3 Cu1 N1 99.57(7) 5_776 . ?
N1 Cu1 N1 180.0 5_776 . ?
N3 Cu1 O1 89.10(7) . . ?
N3 Cu1 O1 90.90(7) 5_776 . ?
N1 Cu1 O1 84.44(6) 5_776 . ?
N1 Cu1 O1 95.56(6) . . ?
Cl1 O1 Cu1 129.65(9) . . ?
C4 N3 Cu1 116.89(16) . . ?
C4 N3 H3 110(2) . . ?
Cu1 N3 H3 133(2) . . ?
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 . . ?
N3 C4 N2 114.21(18) . . ?
N3 C4 C5 127.9(2) . . ?
N2 C4 C5 117.85(18) . . ?
O3 Cl1 O2 110.26(12) . . ?
O3 Cl1 O1 109.68(11) . . ?
O2 Cl1 O1 110.33(10) . . ?
O3 Cl1 O4 108.80(12) . . ?
O2 Cl1 O4 109.17(12) . . ?
O1 Cl1 O4 108.57(11) . . ?
C1 N1 N2 105.90(16) . . ?
C1 N1 Cu1 143.21(15) . . ?
N2 N1 Cu1 110.89(13) . . ?
C3 N2 N1 110.40(18) . . ?
C3 N2 C4 132.11(18) . . ?
N1 N2 C4 117.44(15) . . ?
C2 C3 N2 107.23(19) . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
N1 C1 C2 110.7(2) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 105.80(19) . . ?
C3 C2 H2 127.1 . . ?
C1 C2 H2 127.1 . . ?

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 C4 N2 -4.1(2) . . . . ?
Cu1 N3 C4 C5 175.82(17) . . . . ?
Cu1 O1 Cl1 O3 -128.24(14) . . . . ?
Cu1 O1 Cl1 O2 -6.60(18) . . . . ?
Cu1 O1 Cl1 O4 113.00(13) . . . . ?
C1 N1 N2 C3 0.3(2) . . . . ?
Cu1 N1 N2 C3 -179.92(14) . . . . ?
C1 N1 N2 C4 178.00(18) . . . . ?
Cu1 N1 N2 C4 -2.2(2) . . . . ?
N3 C4 N2 C3 -178.7(2) . . . . ?
C5 C4 N2 C3 1.4(3) . . . . ?
N3 C4 N2 N1 4.2(3) . . . . ?
C5 C4 N2 N1 -175.73(18) . . . . ?
N1 N2 C3 C2 -0.5(2) . . . . ?
C4 N2 C3 C2 -177.7(2) . . . . ?
N2 N1 C1 C2 0.0(2) . . . . ?
Cu1 N1 C1 C2 -179.68(19) . . . . ?
N2 C3 C2 C1 0.4(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.072


####################################################################### 
# 
# 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_Cpd2
_database_code_depnum_ccdc_archive 'CCDC 2222618'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Cl2 Cu N6 O8'
_chemical_formula_weight         508.76

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.0614(3)
_cell_length_b                   15.8795(6)
_cell_length_c                   8.9357(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.1762(19)
_cell_angle_gamma                90
_cell_volume                     951.98(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5087
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.66

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.484
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11225
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         28.773
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2474
_reflns_number_gt                2251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2474
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.479
_refine_ls_restrained_S_all      1.479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.000000 0.000000 0.02029(8) Uani 1 2 d S . P . .
Cl1 Cl 0.09839(6) 0.12203(3) -0.25054(5) 0.02275(10) Uani 1 1 d . . . . .
O1 O 0.2945(2) 0.12814(10) -0.13858(19) 0.0420(4) Uani 1 1 d . . . . .
N1 N 0.4764(2) 0.04505(10) 0.20021(17) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.6267(2) 0.10046(9) 0.26817(16) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.7300(2) 0.07858(10) 0.05793(17) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.804448 0.086455 -0.003617 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7644(2) 0.11703(11) 0.1889(2) 0.0188(3) Uani 1 1 d . . . . .
C6 C 1.0418(3) 0.20952(14) 0.1601(2) 0.0317(4) Uani 1 1 d . . . . .
H6A H 0.947345 0.238889 0.071384 0.047 Uiso 1 1 calc R U . . .
H6B H 1.104027 0.163119 0.120258 0.047 Uiso 1 1 calc R U . . .
H6C H 1.144842 0.249000 0.218882 0.047 Uiso 1 1 calc R U . . .
C2 C 0.4447(3) 0.09481(13) 0.4262(2) 0.0258(4) Uani 1 1 d . . . . .
H2 H 0.392811 0.103625 0.511095 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6096(3) 0.13087(12) 0.4060(2) 0.0226(4) Uani 1 1 d . . . . .
H3A H 0.696431 0.169850 0.474908 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9319(3) 0.17476(12) 0.2680(2) 0.0223(4) Uani 1 1 d . . . . .
H5A H 1.028177 0.144115 0.355633 0.027 Uiso 1 1 calc R U . . .
H5B H 0.878846 0.222468 0.314043 0.027 Uiso 1 1 calc R U . . .
C1 C 0.3667(3) 0.04182(12) 0.2955(2) 0.0240(4) Uani 1 1 d . . . . .
H1 H 0.250570 0.008184 0.278126 0.029 Uiso 1 1 calc R U . . .
O3 O 0.0918(3) 0.05907(10) -0.36494(17) 0.0423(4) Uani 1 1 d . . . . .
O4 O 0.0435(3) 0.20169(10) -0.3254(2) 0.0527(5) Uani 1 1 d . . . . .
O2 O -0.0387(3) 0.09942(17) -0.1703(3) 0.0821(8) 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 N1 1.9814(15) 3_655 ?
Cu1 N1 1.9814(15) . ?
Cu1 N3 1.9847(15) . ?
Cu1 N3 1.9848(15) 3_655 ?
Cu1 O1 2.5802(15) . ?
Cl1 O2 1.4191(17) . ?
Cl1 O3 1.4202(15) . ?
Cl1 O4 1.4271(17) . ?
Cl1 O1 1.4367(14) . ?
N1 C1 1.319(2) . ?
N1 N2 1.367(2) . ?
N2 C3 1.363(2) . ?
N2 C4 1.395(2) . ?
N3 C4 1.274(2) . ?
C4 C5 1.489(2) . ?
C6 C5 1.517(3) . ?
C2 C3 1.359(3) . ?
C2 C1 1.405(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
N1 Cu1 N1 180.0 3_655 . ?
N1 Cu1 N3 99.78(6) 3_655 . ?
N1 Cu1 N3 80.22(6) . . ?
N1 Cu1 N3 80.22(6) 3_655 3_655 ?
N1 Cu1 N3 99.78(6) . 3_655 ?
N3 Cu1 N3 180.0 . 3_655 ?
N1 Cu1 O1 92.55(6) 3_655 . ?
N1 Cu1 O1 87.45(6) . . ?
N3 Cu1 O1 85.49(5) . . ?
N3 Cu1 O1 94.51(5) 3_655 . ?
O2 Cl1 O3 108.15(12) . . ?
O2 Cl1 O4 109.44(15) . . ?
O3 Cl1 O4 110.09(10) . . ?
O2 Cl1 O1 109.06(12) . . ?
O3 Cl1 O1 110.90(10) . . ?
O4 Cl1 O1 109.18(9) . . ?
Cl1 O1 Cu1 123.82(9) . . ?
C1 N1 N2 105.62(14) . . ?
C1 N1 Cu1 143.20(13) . . ?
N2 N1 Cu1 111.18(11) . . ?
C3 N2 N1 110.74(14) . . ?
C3 N2 C4 131.65(15) . . ?
N1 N2 C4 117.60(14) . . ?
C4 N3 Cu1 116.53(12) . . ?
N3 C4 N2 114.39(16) . . ?
N3 C4 C5 128.78(17) . . ?
N2 C4 C5 116.82(15) . . ?
C3 C2 C1 105.78(16) . . ?
C2 C3 N2 106.96(16) . . ?
C4 C5 C6 114.21(15) . . ?
N1 C1 C2 110.90(17) . . ?

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.456
_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_Cpd7
_database_code_depnum_ccdc_archive 'CCDC 2222623'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 B2 Cu F8 N6'
_chemical_formula_weight         455.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.5827(7)
_cell_length_b                   5.9982(3)
_cell_length_c                   18.2326(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.341(3)
_cell_angle_gamma                90
_cell_volume                     1702.75(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3143
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            blue-purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10949
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         28.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2201
_reflns_number_gt                1792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+4.2456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 1.18372(10) 0.7795(3) 0.68768(8) 0.0496(4) Uani 1 1 d . . . . .
N3 N 0.98111(12) 1.1859(3) 0.58702(10) 0.0252(4) Uani 1 1 d . . . . .
H3 H 1.0112 1.3076 0.5961 0.030 Uiso 1 1 calc R U . . .
C4 C 0.92338(13) 1.1213(4) 0.62935(11) 0.0233(4) Uani 1 1 d . . . . .
Cu1 Cu 1.0000 1.0000 0.5000 0.02190(12) Uani 1 2 d S . P . .
N1 N 0.90437(11) 0.8341(3) 0.54204(9) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.87860(11) 0.9328(3) 0.60499(9) 0.0222(4) Uani 1 1 d . . . . .
C3 C 0.81386(14) 0.8145(4) 0.63433(12) 0.0311(5) Uani 1 1 d . . . . .
H3A H 0.7858 0.8490 0.6782 0.037 Uiso 1 1 calc R U . . .
C1 C 0.85525(15) 0.6564(4) 0.53236(13) 0.0290(5) Uani 1 1 d . . . . .
H1 H 0.8586 0.5548 0.4926 0.035 Uiso 1 1 calc R U . . .
C2 C 0.79688(15) 0.6384(5) 0.58946(13) 0.0339(5) Uani 1 1 d . . . . .
H2 H 0.7546 0.5264 0.5952 0.041 Uiso 1 1 calc R U . . .
C5 C 0.89977(16) 1.2212(4) 0.69988(12) 0.0324(5) Uani 1 1 d . . . . .
H5A H 0.9308 1.3620 0.7075 0.049 Uiso 1 1 calc R U . . .
H5B H 0.9151 1.1183 0.7401 0.049 Uiso 1 1 calc R U . . .
H5C H 0.8378 1.2494 0.6988 0.049 Uiso 1 1 calc R U . . .
B1 B 1.11407(15) 0.7023(4) 0.64724(13) 0.0246(5) Uani 1 1 d . . . . .
F1 F 1.11573(9) 0.7858(2) 0.57550(7) 0.0339(3) Uani 1 1 d . . . . .
F4 F 1.11837(12) 0.4703(3) 0.64366(9) 0.0458(4) Uani 1 1 d . . . . .
F2 F 1.03912(11) 0.7628(4) 0.67829(10) 0.0601(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
F3 B1 1.368(3) . ?
N3 C4 1.270(3) . ?
N3 Cu1 1.9710(18) . ?
N3 H3 0.8800 . ?
C4 N2 1.392(3) . ?
C4 C5 1.479(3) . ?
Cu1 N1 1.9727(17) 5_776 ?
Cu1 N1 1.9728(17) . ?
Cu1 N3 1.9710(18) 5_776 ?
Cu1 F1 2.5680(14) . ?
N1 C1 1.320(3) . ?
N1 N2 1.366(2) . ?
N2 C3 1.361(3) . ?
C3 C2 1.355(4) . ?
C3 H3A 0.9500 . ?
C1 C2 1.414(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
B1 F2 1.368(3) . ?
B1 F4 1.395(3) . ?
B1 F1 1.402(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
C4 N3 Cu1 116.72(16) . . ?
C4 N3 H3 121.6 . . ?
Cu1 N3 H3 121.6 . . ?
N3 C4 N2 114.35(19) . . ?
N3 C4 C5 127.8(2) . . ?
N2 C4 C5 117.87(19) . . ?
N1 Cu1 N1 180.0 5_776 . ?
N1 Cu1 N3 99.63(8) 5_776 . ?
N1 Cu1 N3 80.37(8) . . ?
N1 Cu1 N3 80.37(8) 5_776 5_776 ?
N1 Cu1 N3 99.63(8) . 5_776 ?
N3 Cu1 N3 180.0 . 5_776 ?
N1 Cu1 F1 86.30(6) 5_776 . ?
N1 Cu1 F1 93.70(6) . . ?
N3 Cu1 F1 88.64(6) . . ?
N3 Cu1 F1 91.37(6) 5_776 . ?
C1 N1 N2 105.87(17) . . ?
C1 N1 Cu1 143.00(16) . . ?
N2 N1 Cu1 111.12(13) . . ?
C3 N2 N1 110.63(19) . . ?
C3 N2 C4 131.92(19) . . ?
N1 N2 C4 117.35(16) . . ?
C2 C3 N2 107.4(2) . . ?
C2 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
N1 C1 C2 110.5(2) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 105.6(2) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
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 . . ?
F2 B1 F3 111.1(2) . . ?
F2 B1 F4 109.1(2) . . ?
F3 B1 F4 108.9(2) . . ?
F2 B1 F1 109.89(19) . . ?
F3 B1 F1 109.74(19) . . ?
F4 B1 F1 108.06(19) . . ?
B1 F1 Cu1 129.76(13) . . ?

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 C4 N2 -3.4(2) . . . . ?
Cu1 N3 C4 C5 176.18(18) . . . . ?
C1 N1 N2 C3 0.4(2) . . . . ?
Cu1 N1 N2 C3 -178.73(14) . . . . ?
C1 N1 N2 C4 177.37(18) . . . . ?
Cu1 N1 N2 C4 -1.8(2) . . . . ?
N3 C4 N2 C3 179.6(2) . . . . ?
C5 C4 N2 C3 0.0(3) . . . . ?
N3 C4 N2 N1 3.5(3) . . . . ?
C5 C4 N2 N1 -176.17(18) . . . . ?
N1 N2 C3 C2 -0.6(3) . . . . ?
C4 N2 C3 C2 -177.0(2) . . . . ?
N2 N1 C1 C2 -0.1(2) . . . . ?
Cu1 N1 C1 C2 178.65(19) . . . . ?
N2 C3 C2 C1 0.6(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
F2 B1 F1 Cu1 -3.9(3) . . . . ?
F3 B1 F1 Cu1 -126.28(17) . . . . ?
F4 B1 F1 Cu1 115.07(18) . . . . ?

_refine_diff_density_max         0.568
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_Cpd10
_database_code_depnum_ccdc_archive 'CCDC 2240845'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 B2 Cl2 Cu2 F8 N10'
_chemical_formula_weight         754.11

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.6757(4)
_cell_length_b                   14.7202(8)
_cell_length_c                   14.3589(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.853(3)
_cell_angle_gamma                90
_cell_volume                     1407.83(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8627
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.70

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             1014
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.784
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19931
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         28.868
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3653
_reflns_number_gt                3314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+5.1843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3653
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_restrained_S_all      0.851
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51053(4) 0.05621(2) 0.60838(2) 0.01547(10) Uani 1 1 d . . . . .
Cl1 Cl 0.26163(9) 0.06694(4) 0.49333(4) 0.01827(13) Uani 1 1 d . . . . .
B1 B 0.2473(5) 0.1594(2) 0.8003(2) 0.0256(6) Uani 1 1 d . . . . .
F1 F 0.2980(3) 0.17466(15) 0.70913(14) 0.0433(5) Uani 1 1 d . . . . .
F3 F 0.2613(3) 0.23950(14) 0.85062(15) 0.0428(5) Uani 1 1 d . . . . .
F4 F 0.3737(3) 0.09519(15) 0.84155(15) 0.0440(5) Uani 1 1 d . . . . .
F2 F 0.0484(3) 0.12854(16) 0.79810(17) 0.0474(5) Uani 1 1 d . . . . .
N1 N 0.3704(3) -0.04386(15) 0.66788(14) 0.0177(4) Uani 1 1 d . . . . .
N3 N 0.7093(3) 0.02785(15) 0.71591(15) 0.0189(4) Uani 1 1 d . . . . .
H3 H 0.8180 0.0608 0.7281 0.023 Uiso 1 1 calc R U . . .
N2 N 0.4849(3) -0.08222(15) 0.73937(15) 0.0191(4) Uani 1 1 d . . . . .
N4 N 0.6556(3) 0.16144(14) 0.56114(14) 0.0170(4) Uani 1 1 d . . . . .
N5 N 0.5691(3) 0.21910(15) 0.49711(15) 0.0204(4) Uani 1 1 d . . . . .
H5 H 0.4414 0.2177 0.4775 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6686(4) -0.04018(18) 0.76486(18) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.2075(5) -0.1629(2) 0.7240(2) 0.0291(6) Uani 1 1 d . . . . .
H2 H 0.1061 -0.2070 0.7318 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8476(4) 0.18705(18) 0.57240(18) 0.0198(5) Uani 1 1 d . . . . .
H7 H 0.9457 0.1591 0.6140 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3872(5) -0.15507(19) 0.7744(2) 0.0263(6) Uani 1 1 d . . . . .
H3A H 0.4355 -0.1931 0.8245 0.032 Uiso 1 1 calc R U . . .
C1 C 0.2036(4) -0.09188(19) 0.65776(19) 0.0223(5) Uani 1 1 d . . . . .
H1 H 0.0963 -0.0804 0.6125 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8837(4) 0.26049(19) 0.5146(2) 0.0260(6) Uani 1 1 d . . . . .
H8 H 1.0073 0.2914 0.5090 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7024(5) 0.27862(18) 0.4674(2) 0.0254(5) Uani 1 1 d . . . . .
H9 H 0.6764 0.3249 0.4221 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7929(5) -0.0779(2) 0.8471(2) 0.0290(6) Uani 1 1 d . . . . .
H5A H 0.9333 -0.0568 0.8446 0.035 Uiso 1 1 calc R U . . .
H5B H 0.7929 -0.1450 0.8435 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7141(6) -0.0488(2) 0.9389(2) 0.0418(8) Uani 1 1 d . . . . .
H6A H 0.7117 0.0177 0.9423 0.063 Uiso 1 1 calc R U . . .
H6B H 0.8017 -0.0728 0.9906 0.063 Uiso 1 1 calc R U . . .
H6C H 0.5778 -0.0724 0.9432 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.971(2) . ?
Cu1 N1 1.970(2) . ?
Cu1 N3 2.011(2) . ?
Cu1 Cl1 2.2685(6) . ?
Cu1 F1 2.724(2) . ?
B1 F4 1.374(4) . ?
B1 F3 1.383(4) . ?
B1 F1 1.393(4) . ?
B1 F2 1.402(4) . ?
N1 C1 1.319(3) . ?
N1 N2 1.360(3) . ?
N3 C4 1.263(3) . ?
N2 C3 1.368(3) . ?
N2 C4 1.400(3) . ?
N4 C7 1.335(3) . ?
N4 N5 1.352(3) . ?
N5 C9 1.339(4) . ?
C4 C5 1.504(4) . ?
C2 C3 1.364(4) . ?
C2 C1 1.412(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.373(4) . ?
C5 C6 1.513(4) . ?

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
N4 Cu1 N1 174.40(9) . . ?
N4 Cu1 N3 96.50(9) . . ?
N1 Cu1 N3 79.63(9) . . ?
N4 Cu1 Cl1 92.72(6) . . ?
N1 Cu1 Cl1 91.26(6) . . ?
N3 Cu1 Cl1 170.71(7) . . ?
N4 Cu1 F1 88.01(8) . . ?
N1 Cu1 F1 88.22(8) . . ?
N3 Cu1 F1 93.76(8) . . ?
Cl1 Cu1 F1 87.71(5) . . ?
F4 B1 F3 110.1(2) . . ?
F4 B1 F1 109.6(3) . . ?
F3 B1 F1 110.0(3) . . ?
F4 B1 F2 109.9(3) . . ?
F3 B1 F2 108.6(2) . . ?
F1 B1 F2 108.7(2) . . ?
B1 F1 Cu1 124.34(19) . . ?
C1 N1 N2 106.7(2) . . ?
C1 N1 Cu1 140.80(19) . . ?
N2 N1 Cu1 112.24(16) . . ?
C4 N3 Cu1 115.85(18) . . ?
N1 N2 C3 110.2(2) . . ?
N1 N2 C4 116.8(2) . . ?
C3 N2 C4 132.9(2) . . ?
C7 N4 N5 105.5(2) . . ?
C7 N4 Cu1 132.07(18) . . ?
N5 N4 Cu1 122.00(16) . . ?
C9 N5 N4 111.4(2) . . ?
N3 C4 N2 115.0(2) . . ?
N3 C4 C5 127.0(3) . . ?
N2 C4 C5 118.0(2) . . ?
C3 C2 C1 105.7(2) . . ?
N4 C7 C8 110.5(2) . . ?
C2 C3 N2 107.1(2) . . ?
N1 C1 C2 110.2(2) . . ?
C9 C8 C7 105.2(2) . . ?
N5 C9 C8 107.4(2) . . ?
C4 C5 C6 112.0(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
F4 B1 F1 Cu1 20.8(3) . . . . ?
F3 B1 F1 Cu1 141.98(18) . . . . ?
F2 B1 F1 Cu1 -99.3(2) . . . . ?
C1 N1 N2 C3 -0.2(3) . . . . ?
Cu1 N1 N2 C3 -175.94(18) . . . . ?
C1 N1 N2 C4 -178.0(2) . . . . ?
Cu1 N1 N2 C4 6.3(3) . . . . ?
C7 N4 N5 C9 1.0(3) . . . . ?
Cu1 N4 N5 C9 -172.59(18) . . . . ?
Cu1 N3 C4 N2 -3.4(3) . . . . ?
Cu1 N3 C4 C5 178.2(2) . . . . ?
N1 N2 C4 N3 -2.0(3) . . . . ?
C3 N2 C4 N3 -179.1(3) . . . . ?
N1 N2 C4 C5 176.6(2) . . . . ?
C3 N2 C4 C5 -0.6(4) . . . . ?
N5 N4 C7 C8 -0.7(3) . . . . ?
Cu1 N4 C7 C8 171.94(19) . . . . ?
C1 C2 C3 N2 0.1(3) . . . . ?
N1 N2 C3 C2 0.0(3) . . . . ?
C4 N2 C3 C2 177.3(3) . . . . ?
N2 N1 C1 C2 0.3(3) . . . . ?
Cu1 N1 C1 C2 174.0(2) . . . . ?
C3 C2 C1 N1 -0.2(3) . . . . ?
N4 C7 C8 C9 0.2(3) . . . . ?
N4 N5 C9 C8 -0.9(3) . . . . ?
C7 C8 C9 N5 0.4(3) . . . . ?
N3 C4 C5 C6 100.6(4) . . . . ?
N2 C4 C5 C6 -77.8(3) . . . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.093

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Cpd3
_database_code_depnum_ccdc_archive 'CCDC 2222619'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 Cl4 Cu2 N6'
_chemical_formula_weight         487.17

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.279(3)
_cell_length_b                   9.550(3)
_cell_length_c                   11.678(4)
_cell_angle_alpha                94.69(2)
_cell_angle_beta                 104.15(2)
_cell_angle_gamma                106.77(3)
_cell_volume                     845.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1491
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.05

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    3.149
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8038
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4066
_reflns_number_gt                1824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1790
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   0.797
_refine_ls_restrained_S_all      0.797
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.04798(10) 0.78230(8) 0.80325(6) 0.0414(2) Uani 1 1 d . . . . .
Cu2 Cu 0.44134(10) 0.76225(9) 0.75606(7) 0.0469(3) Uani 1 1 d . . . . .
Cl2 Cl 0.1375(2) 0.58111(17) 0.77784(14) 0.0494(4) Uani 1 1 d . . . . .
Cl4 Cl 0.3553(2) 0.96770(18) 0.77233(15) 0.0523(4) Uani 1 1 d . . . . .
Cl1 Cl 0.1292(2) 0.8164(2) 1.00368(13) 0.0591(5) Uani 1 1 d . . . . .
N6 N 0.5536(7) 0.7971(6) 0.9343(5) 0.0527(15) Uani 1 1 d . . . . .
H9 H 0.544828 0.868334 0.981407 0.063 Uiso 1 1 calc R U . . .
N1 N -0.0633(7) 0.7608(6) 0.6273(4) 0.0441(13) Uani 1 1 d . . . . .
N4 N 0.5649(7) 0.6093(6) 0.7721(5) 0.0481(13) Uani 1 1 d . . . . .
N3 N -0.0773(7) 0.9344(6) 0.7978(4) 0.0488(14) Uani 1 1 d . . . . .
H4 H -0.082466 0.981830 0.862953 0.059 Uiso 1 1 calc R U . . .
N2 N -0.1421(6) 0.8664(6) 0.6012(4) 0.0429(13) Uani 1 1 d . . . . .
C4 C -0.1484(8) 0.9580(7) 0.6956(5) 0.0409(14) Uani 1 1 d . . . . .
C9 C 0.6365(8) 0.7122(7) 0.9749(5) 0.0459(16) Uani 1 1 d . . . . .
C5 C -0.2388(10) 1.0719(8) 0.6691(6) 0.0596(19) Uani 1 1 d . . . . .
H5A H -0.226597 1.132691 0.743406 0.089 Uiso 1 1 calc R U . . .
H5B H -0.362522 1.022526 0.629034 0.089 Uiso 1 1 calc R U . . .
H5C H -0.185892 1.134074 0.617762 0.089 Uiso 1 1 calc R U . . .
C3 C -0.2049(9) 0.8550(9) 0.4802(6) 0.0587(19) Uani 1 1 d . . . . .
H3 H -0.264082 0.914524 0.439121 0.070 Uiso 1 1 calc R U . . .
C1 C -0.0787(10) 0.6856(8) 0.5264(6) 0.062(2) Uani 1 1 d . . . . .
H1 H -0.037506 0.604369 0.518288 0.074 Uiso 1 1 calc R U . . .
C2 C -0.1643(10) 0.7401(9) 0.4309(6) 0.068(2) Uani 1 1 d . . . . .
H2 H -0.189047 0.704679 0.348952 0.081 Uiso 1 1 calc R U . . .
Cl3 Cl 0.3856(3) 0.7258(2) 0.55729(15) 0.0646(5) Uani 1 1 d . . . . .
C10 C 0.7235(9) 0.7122(7) 1.1017(6) 0.0581(19) Uani 1 1 d . . . . .
H10A H 0.714512 0.794202 1.151804 0.087 Uiso 1 1 calc R U . . .
H10B H 0.846380 0.722771 1.111391 0.087 Uiso 1 1 calc R U . . .
H10C H 0.666565 0.619549 1.125069 0.087 Uiso 1 1 calc R U . . .
C6 C 0.5931(9) 0.5045(7) 0.7120(7) 0.0551(18) Uani 1 1 d . . . . .
H6 H 0.554232 0.480718 0.628005 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7215(10) 0.4968(8) 0.8979(7) 0.063(2) Uani 1 1 d . . . . .
H8 H 0.785684 0.473939 0.967980 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6887(10) 0.4294(9) 0.7856(7) 0.069(2) Uani 1 1 d . . . . .
H7 H 0.722538 0.348632 0.761150 0.082 Uiso 1 1 calc R U . . .
N5 N 0.6432(6) 0.6061(5) 0.8908(4) 0.0403(12) 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 N1 2.003(5) . ?
Cu1 N3 2.010(5) . ?
Cu1 Cl1 2.2397(18) . ?
Cu1 Cl2 2.2724(18) . ?
Cu2 N4 2.007(5) . ?
Cu2 N6 2.018(5) . ?
Cu2 Cl3 2.2301(19) . ?
Cu2 Cl4 2.2814(19) . ?
Cu2 Cl2 2.695(2) . ?
N6 C9 1.256(8) . ?
N1 C1 1.286(8) . ?
N1 N2 1.366(7) . ?
N4 C6 1.284(8) . ?
N4 N5 1.386(7) . ?
N3 C4 1.265(7) . ?
N2 C3 1.365(8) . ?
N2 C4 1.371(8) . ?
C4 C5 1.500(8) . ?
C9 N5 1.375(8) . ?
C9 C10 1.480(8) . ?
C3 C2 1.361(11) . ?
C1 C2 1.392(10) . ?
C6 C7 1.405(10) . ?
C8 C7 1.339(10) . ?
C8 N5 1.376(8) . ?

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
N1 Cu1 N3 78.2(2) . . ?
N1 Cu1 Cl1 169.56(16) . . ?
N3 Cu1 Cl1 92.93(15) . . ?
N1 Cu1 Cl2 92.12(15) . . ?
N3 Cu1 Cl2 167.72(15) . . ?
Cl1 Cu1 Cl2 95.85(7) . . ?
N4 Cu2 N6 78.2(2) . . ?
N4 Cu2 Cl3 92.06(17) . . ?
N6 Cu2 Cl3 165.43(18) . . ?
N4 Cu2 Cl4 166.94(15) . . ?
N6 Cu2 Cl4 91.13(16) . . ?
Cl3 Cu2 Cl4 96.90(7) . . ?
N4 Cu2 Cl2 94.67(17) . . ?
N6 Cu2 Cl2 91.77(18) . . ?
Cl3 Cu2 Cl2 99.87(7) . . ?
Cl4 Cu2 Cl2 93.14(7) . . ?
Cu1 Cl2 Cu2 88.79(6) . . ?
C9 N6 Cu2 117.6(5) . . ?
C1 N1 N2 106.5(5) . . ?
C1 N1 Cu1 141.5(5) . . ?
N2 N1 Cu1 111.8(4) . . ?
C6 N4 N5 104.9(5) . . ?
C6 N4 Cu2 143.0(5) . . ?
N5 N4 Cu2 111.9(4) . . ?
C4 N3 Cu1 117.1(5) . . ?
C3 N2 N1 110.1(6) . . ?
C3 N2 C4 132.4(6) . . ?
N1 N2 C4 117.5(4) . . ?
N3 C4 N2 114.8(5) . . ?
N3 C4 C5 126.8(6) . . ?
N2 C4 C5 118.4(5) . . ?
N6 C9 N5 115.4(5) . . ?
N6 C9 C10 127.5(7) . . ?
N5 C9 C10 117.1(5) . . ?
C2 C3 N2 106.1(6) . . ?
N1 C1 C2 111.2(7) . . ?
C3 C2 C1 106.1(6) . . ?
N4 C6 C7 112.5(6) . . ?
C7 C8 N5 106.7(6) . . ?
C8 C7 C6 105.8(6) . . ?
C9 N5 C8 133.2(5) . . ?
C9 N5 N4 116.7(5) . . ?
C8 N5 N4 110.0(5) . . ?

_refine_diff_density_max         1.896
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.179


####################################################################### 
# 
# 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_Cu(pzH)4(BF4)2
_database_code_depnum_ccdc_archive 'CCDC 2222625'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 B2 Cu F8 N8'
_chemical_formula_weight         509.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.0051(8)
_cell_length_b                   9.8734(5)
_cell_length_c                   15.5093(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.108(3)
_cell_angle_gamma                90
_cell_volume                     1957.54(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4383
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.87

_exptl_crystal_description       block
_exptl_crystal_colour            blue-purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.208
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12837
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         28.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2545
_reflns_number_gt                2109
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2545
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1805
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.0000 0.0199(2) Uani 1 2 d S . P . .
N3 N 0.37417(16) 0.1299(2) 0.05750(15) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.2455(2) 0.2732(2) 0.12692(17) 0.0239(5) Uani 1 1 d . . . . .
N2 N 0.3059(2) 0.3392(3) 0.20509(19) 0.0439(7) Uani 1 1 d . . . . .
H2 H 0.3598 0.3899 0.2109 0.053 Uiso 1 1 calc R U . . .
N4 N 0.37168(19) -0.0048(3) 0.04916(19) 0.0333(6) Uani 1 1 d . . . . .
H4 H 0.3150 -0.0514 0.0158 0.040 Uiso 1 1 calc R U . . .
C1 C 0.17317(19) 0.2067(3) 0.14895(17) 0.0216(5) Uani 1 1 d . . . . .
H1 H 0.1204 0.1491 0.1068 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4731(2) 0.1604(3) 0.1127(2) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.4990 0.2496 0.1308 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2714(2) 0.3166(3) 0.2767(2) 0.0370(7) Uani 1 1 d . . . . .
H3 H 0.3006 0.3513 0.3393 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5336(2) 0.0425(3) 0.1403(2) 0.0397(7) Uani 1 1 d . . . . .
H5 H 0.6061 0.0354 0.1800 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1859(3) 0.2329(3) 0.2366(3) 0.0348(7) Uani 1 1 d . . . . .
H2A H 0.1435 0.1998 0.2667 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4652(2) -0.0601(3) 0.0974(3) 0.0464(9) Uani 1 1 d . . . . .
H4A H 0.4814 -0.1540 0.1012 0.056 Uiso 1 1 calc R U . . .
B1 B 0.4056(2) 0.5629(3) 0.0622(2) 0.0264(6) Uani 1 1 d . . . . .
F1 F 0.36220(14) 0.44000(18) 0.01814(14) 0.0374(5) Uani 1 1 d . . . . .
F4 F 0.44492(14) 0.63324(18) 0.00786(13) 0.0408(5) Uani 1 1 d . . . . .
F3 F 0.32670(15) 0.6355(2) 0.07236(16) 0.0495(5) Uani 1 1 d . . . . .
F2 F 0.48429(18) 0.5355(3) 0.14887(15) 0.0642(7) 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 1.990(2) . ?
Cu1 N3 1.990(2) 7 ?
Cu1 N1 2.008(2) 7 ?
Cu1 N1 2.008(2) . ?
Cu1 F1 2.3887(16) 7 ?
Cu1 F1 2.3888(16) . ?
N3 C6 1.333(3) . ?
N3 N4 1.335(3) . ?
N1 N2 1.331(4) . ?
N1 C1 1.362(3) . ?
N2 C3 1.398(4) . ?
N4 C4 1.331(4) . ?
C1 C2 1.323(4) . ?
C6 C5 1.400(4) . ?
C3 C2 1.377(5) . ?
C5 C4 1.367(4) . ?
B1 F4 1.370(3) . ?
B1 F2 1.373(4) . ?
B1 F3 1.379(4) . ?
B1 F1 1.403(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 180.0 . 7 ?
N3 Cu1 N1 89.98(9) . 7 ?
N3 Cu1 N1 90.02(9) 7 7 ?
N3 Cu1 N1 90.02(9) . . ?
N3 Cu1 N1 89.98(9) 7 . ?
N1 Cu1 N1 180.0 7 . ?
N3 Cu1 F1 89.83(8) . 7 ?
N3 Cu1 F1 90.16(8) 7 7 ?
N1 Cu1 F1 94.45(8) 7 7 ?
N1 Cu1 F1 85.55(8) . 7 ?
N3 Cu1 F1 90.17(8) . . ?
N3 Cu1 F1 89.84(8) 7 . ?
N1 Cu1 F1 85.55(8) 7 . ?
N1 Cu1 F1 94.45(8) . . ?
F1 Cu1 F1 180.0 7 . ?
C6 N3 N4 105.5(2) . . ?
C6 N3 Cu1 129.98(19) . . ?
N4 N3 Cu1 124.53(17) . . ?
N2 N1 C1 105.6(2) . . ?
N2 N1 Cu1 133.3(2) . . ?
C1 N1 Cu1 121.01(19) . . ?
N1 N2 C3 110.4(3) . . ?
C4 N4 N3 111.9(2) . . ?
C2 C1 N1 111.2(3) . . ?
N3 C6 C5 110.4(2) . . ?
C2 C3 N2 104.8(3) . . ?
C4 C5 C6 104.5(3) . . ?
C1 C2 C3 108.0(3) . . ?
N4 C4 C5 107.6(3) . . ?
F4 B1 F2 109.8(2) . . ?
F4 B1 F3 110.4(3) . . ?
F2 B1 F3 110.6(3) . . ?
F4 B1 F1 110.0(2) . . ?
F2 B1 F1 108.7(3) . . ?
F3 B1 F1 107.3(2) . . ?
B1 F1 Cu1 150.40(17) . . ?

_refine_diff_density_max         1.384
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Cpd4
_database_code_depnum_ccdc_archive 'CCDC 2222620'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 Cl2 Cu N3'
_chemical_formula_weight         257.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.4981(3)
_cell_length_b                   6.8635(3)
_cell_length_c                   16.2694(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.120(2)
_cell_angle_gamma                90
_cell_volume                     924.17(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2367
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.43

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             474
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.887
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9864
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.504
_diffrn_reflns_theta_max         28.692
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2391
_reflns_number_gt                1877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2391
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   0.670
_refine_ls_restrained_S_all      0.670
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.70993(4) 0.61509(4) 0.16689(2) 0.01982(12) Uani 1 1 d . . . . .
Cl1 Cl 0.89078(7) 0.76310(9) 0.10587(4) 0.02217(15) Uani 1 1 d . . . . .
Cl2 Cl 0.89519(8) 0.47988(10) 0.27254(4) 0.02715(16) Uani 1 1 d . . . . .
C2 C 0.3127(3) 0.7710(4) -0.03248(17) 0.0272(6) Uani 1 1 d . . . . .
H2 H 0.255812 0.828451 -0.082156 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3892(3) 0.5071(4) 0.16331(15) 0.0221(5) Uani 1 1 d . . . . .
C3 C 0.2503(3) 0.6746(4) 0.02607(17) 0.0253(5) Uani 1 1 d . . . . .
H3 H 0.141428 0.654298 0.024338 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2387(3) 0.4273(4) 0.18221(18) 0.0275(6) Uani 1 1 d . . . . .
H5A H 0.155330 0.526609 0.170832 0.033 Uiso 1 1 calc R U . . .
H5B H 0.258655 0.394876 0.241707 0.033 Uiso 1 1 calc R U . . .
C1 C 0.4816(3) 0.7655(4) -0.00193(16) 0.0220(5) Uani 1 1 d . . . . .
H1 H 0.555478 0.821030 -0.029276 0.026 Uiso 1 1 calc R U . . .
N1 N 0.5213(3) 0.6714(3) 0.07037(13) 0.0193(4) Uani 1 1 d . . . . .
N2 N 0.3783(3) 0.6132(3) 0.08802(13) 0.0206(4) Uani 1 1 d . . . . .
N3 N 0.5314(3) 0.4904(3) 0.20692(14) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.550454 0.425668 0.253398 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1781(4) 0.2455(5) 0.12995(19) 0.0356(7) Uani 1 1 d . . . . .
H6A H 0.157973 0.276844 0.070979 0.053 Uiso 1 1 calc R U . . .
H6B H 0.079894 0.200863 0.143451 0.053 Uiso 1 1 calc R U . . .
H6C H 0.258401 0.144883 0.142683 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.977(2) . ?
Cu1 N1 2.011(2) . ?
Cu1 Cl2 2.2508(7) . ?
Cu1 Cl1 2.2522(7) . ?
C2 C3 1.362(4) . ?
C2 C1 1.408(4) . ?
C4 N3 1.260(3) . ?
C4 N2 1.410(3) . ?
C4 C5 1.486(4) . ?
C3 N2 1.370(3) . ?
C5 C6 1.532(4) . ?
C1 N1 1.317(3) . ?
N1 N2 1.370(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 N1 78.75(9) . . ?
N3 Cu1 Cl2 91.49(6) . . ?
N1 Cu1 Cl2 166.22(6) . . ?
N3 Cu1 Cl1 172.82(6) . . ?
N1 Cu1 Cl1 94.13(6) . . ?
Cl2 Cu1 Cl1 95.37(2) . . ?
C3 C2 C1 105.5(2) . . ?
N3 C4 N2 113.7(2) . . ?
N3 C4 C5 127.6(2) . . ?
N2 C4 C5 118.7(2) . . ?
C2 C3 N2 107.1(2) . . ?
C4 C5 C6 112.5(2) . . ?
N1 C1 C2 111.3(2) . . ?
C1 N1 N2 105.7(2) . . ?
C1 N1 Cu1 142.10(19) . . ?
N2 N1 Cu1 111.61(15) . . ?
N1 N2 C3 110.5(2) . . ?
N1 N2 C4 116.5(2) . . ?
C3 N2 C4 133.0(2) . . ?
C4 N3 Cu1 118.99(19) . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.093


####################################################################### 
# 
# 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_Cpd5
_database_code_depnum_ccdc_archive 'CCDC 2222621'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl4 Cu2 N10 O8'
_chemical_formula_weight         751.31

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.8239(3)
_cell_length_b                   22.2246(12)
_cell_length_c                   9.5718(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.437(3)
_cell_angle_gamma                90
_cell_volume                     1360.27(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6215
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.70

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.018
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14575
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         28.703
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3492
_reflns_number_gt                3152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.80120(4) 0.02056(2) 0.56323(3) 0.01546(13) Uani 1 1 d . . . . .
Cl1 Cl 0.78905(9) 0.01464(3) 0.32418(6) 0.01869(16) Uani 1 1 d . . . . .
Cl2 Cl 0.75870(10) 0.15553(3) 0.02101(6) 0.02120(16) Uani 1 1 d . . . . .
O4 O 0.8167(4) 0.09316(9) 0.0175(2) 0.0322(5) Uani 1 1 d . . . . .
O1 O 0.6992(4) 0.16514(9) 0.1497(2) 0.0352(5) Uani 1 1 d . . . . .
O3 O 0.5874(4) 0.16982(12) -0.1102(2) 0.0477(7) Uani 1 1 d . . . . .
O2 O 0.9362(4) 0.19197(10) 0.0312(3) 0.0435(6) Uani 1 1 d . . . . .
N3 N 0.7719(3) 0.01423(9) 0.7633(2) 0.0177(4) Uani 1 1 d . . . . .
H3 H 0.788144 0.044910 0.821011 0.021 Uiso 1 1 calc R U . . .
N1 N 0.6965(3) -0.06331(9) 0.5553(2) 0.0180(4) Uani 1 1 d . . . . .
N2 N 0.6949(3) -0.08168(9) 0.6909(2) 0.0174(4) Uani 1 1 d . . . . .
N4 N 0.8698(3) 0.10692(9) 0.5781(2) 0.0184(4) Uani 1 1 d . . . . .
N5 N 0.8628(3) 0.14191(10) 0.4606(2) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.824613 0.129423 0.369982 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7024(4) -0.05516(14) 0.9432(3) 0.0236(5) Uani 1 1 d . . . . .
H5A H 0.742506 -0.022247 1.012321 0.035 Uiso 1 1 calc R U . . .
H5B H 0.789296 -0.089361 0.984426 0.035 Uiso 1 1 calc R U . . .
H5C H 0.558809 -0.065342 0.924734 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7281(4) -0.03742(11) 0.8008(3) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.6250(4) -0.16204(12) 0.5487(3) 0.0262(6) Uani 1 1 d . . . . .
H2 H 0.593973 -0.201148 0.513334 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6536(4) -0.11175(11) 0.4687(3) 0.0220(5) Uani 1 1 d . . . . .
H1 H 0.643883 -0.112336 0.369384 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9352(4) 0.14339(12) 0.6949(3) 0.0244(5) Uani 1 1 d . . . . .
H6 H 0.954524 0.131632 0.792070 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6520(4) -0.14191(12) 0.6882(3) 0.0237(5) Uani 1 1 d . . . . .
H3A H 0.642986 -0.164765 0.767134 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9714(5) 0.20137(12) 0.6547(3) 0.0295(6) Uani 1 1 d . . . . .
H7 H 1.018012 0.234606 0.716418 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9229(4) 0.19834(12) 0.5032(3) 0.0268(6) Uani 1 1 d . . . . .
H8 H 0.930297 0.229832 0.441297 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.969(2) . ?
Cu1 N1 1.988(2) . ?
Cu1 N3 1.999(2) . ?
Cu1 Cl1 2.2643(6) . ?
Cu1 Cl1 2.7363(7) 3_756 ?
Cl2 O3 1.421(2) . ?
Cl2 O2 1.431(2) . ?
Cl2 O1 1.441(2) . ?
Cl2 O4 1.445(2) . ?
N3 C4 1.269(3) . ?
N1 C1 1.327(3) . ?
N1 N2 1.364(3) . ?
N2 C3 1.368(3) . ?
N2 C4 1.400(3) . ?
N4 C6 1.326(3) . ?
N4 N5 1.354(3) . ?
N5 C8 1.338(3) . ?
C5 C4 1.487(3) . ?
C2 C3 1.358(4) . ?
C2 C1 1.407(4) . ?
C6 C7 1.392(4) . ?
C7 C8 1.371(4) . ?

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
N4 Cu1 N1 171.85(8) . . ?
N4 Cu1 N3 95.76(8) . . ?
N1 Cu1 N3 79.37(8) . . ?
N4 Cu1 Cl1 93.06(6) . . ?
N1 Cu1 Cl1 91.22(6) . . ?
N3 Cu1 Cl1 169.59(6) . . ?
N4 Cu1 Cl1 93.77(6) . 3_756 ?
N1 Cu1 Cl1 92.93(6) . 3_756 ?
N3 Cu1 Cl1 91.88(6) . 3_756 ?
Cl1 Cu1 Cl1 93.05(2) . 3_756 ?
Cu1 Cl1 Cu1 86.95(2) . 3_756 ?
O3 Cl2 O2 110.43(17) . . ?
O3 Cl2 O1 109.40(14) . . ?
O2 Cl2 O1 109.99(15) . . ?
O3 Cl2 O4 109.95(14) . . ?
O2 Cl2 O4 108.18(14) . . ?
O1 Cl2 O4 108.88(12) . . ?
C4 N3 Cu1 116.54(17) . . ?
C1 N1 N2 106.1(2) . . ?
C1 N1 Cu1 141.43(18) . . ?
N2 N1 Cu1 111.51(14) . . ?
N1 N2 C3 110.4(2) . . ?
N1 N2 C4 116.85(19) . . ?
C3 N2 C4 132.7(2) . . ?
C6 N4 N5 104.7(2) . . ?
C6 N4 Cu1 131.16(18) . . ?
N5 N4 Cu1 124.15(17) . . ?
C8 N5 N4 111.5(2) . . ?
N3 C4 N2 114.5(2) . . ?
N3 C4 C5 127.9(2) . . ?
N2 C4 C5 117.6(2) . . ?
C3 C2 C1 106.0(2) . . ?
N1 C1 C2 110.3(2) . . ?
N4 C6 C7 111.9(2) . . ?
C2 C3 N2 107.2(2) . . ?
C8 C7 C6 104.3(2) . . ?
N5 C8 C7 107.7(2) . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.076


####################################################################### 
# 
# 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_Cpd09
_database_code_depnum_ccdc_archive 'CCDC 2240844'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 B2 Cl2 Cu2 F8 N10'
_chemical_formula_weight         726.06

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.8088(6)
_cell_length_b                   21.937(2)
_cell_length_c                   9.5062(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.098(6)
_cell_angle_gamma                90
_cell_volume                     1333.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4331
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.20

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             1300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.880
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  0.730
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14776
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.857
_diffrn_reflns_theta_max         28.709
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3422
_reflns_number_gt                2639
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3422
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1557
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.20145(7) 0.97879(2) 0.93768(5) 0.01887(17) Uani 1 1 d . . . . .
Cl1 Cl 0.20966(14) 0.98539(4) 1.17721(10) 0.0219(2) Uani 1 1 d . . . . .
N3 N 0.2300(5) 0.98514(13) 0.7356(4) 0.0203(7) Uani 1 1 d . . . . .
H1 H 0.2132 0.9533 0.6763 0.024 Uiso 1 1 calc R U . . .
N1 N 0.3056(5) 1.06400(14) 0.9448(3) 0.0206(7) Uani 1 1 d . . . . .
N4 N 0.1339(5) 0.89109(14) 0.9243(4) 0.0204(7) Uani 1 1 d . . . . .
N2 N 0.3047(5) 1.08268(14) 0.8083(4) 0.0216(7) Uani 1 1 d . . . . .
N5 N 0.1370(5) 0.85622(14) 1.0418(4) 0.0227(7) Uani 1 1 d . . . . .
H2 H 0.1746 0.8695 1.1347 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2735(6) 1.03745(18) 0.6975(4) 0.0221(8) Uani 1 1 d . . . . .
C2 C 0.3718(6) 1.16428(19) 0.9485(5) 0.0297(9) Uani 1 1 d . . . . .
H3 H 0.4029 1.2049 0.9838 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2966(6) 1.0559(2) 0.5539(4) 0.0279(9) Uani 1 1 d . . . . .
H4 H 0.4439 1.0648 0.5704 0.042 Uiso 1 1 calc R U . . .
H5 H 0.2122 1.0923 0.5153 0.042 Uiso 1 1 calc R U . . .
H6 H 0.2490 1.0227 0.4811 0.042 Uiso 1 1 calc R U . . .
C1 C 0.3456(6) 1.11315(17) 1.0309(5) 0.0239(8) Uani 1 1 d . . . . .
H7 H 0.3552 1.1139 1.1329 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3433(6) 1.14333(18) 0.8082(5) 0.0272(9) Uani 1 1 d . . . . .
H8 H 0.3494 1.1667 0.7257 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0301(7) 0.79591(19) 0.8494(5) 0.0340(10) Uani 1 1 d . . . . .
H9 H -0.0183 0.7614 0.7866 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0691(6) 0.85402(18) 0.8067(5) 0.0271(9) Uani 1 1 d . . . . .
H10 H 0.0517 0.8657 0.7069 0.032 Uiso 1 1 calc R U . . .
C8 C 0.0759(6) 0.79896(18) 1.0001(5) 0.0281(9) Uani 1 1 d . . . . .
H11 H 0.0665 0.7666 1.0638 0.034 Uiso 1 1 calc R U . . .
B1 B 0.2403(8) 0.8458(2) 0.4786(5) 0.0273(10) Uani 1 1 d . . . . .
F2 F 0.1802(4) 0.90628(11) 0.4842(3) 0.0390(7) Uani 1 1 d . . . . .
F3 F 0.2950(5) 0.83736(11) 0.3524(3) 0.0393(7) Uani 1 1 d . . . . .
F4 F 0.0701(5) 0.80953(12) 0.4712(4) 0.0532(8) Uani 1 1 d . . . . .
F1 F 0.4059(5) 0.83191(16) 0.6041(3) 0.0601(9) 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 N4 1.972(3) . ?
Cu1 N1 1.992(3) . ?
Cu1 N3 2.001(3) . ?
Cu1 Cl1 2.2631(10) . ?
Cu1 Cl1 2.7468(11) 3_577 ?
Cl1 Cu1 2.7467(10) 3_577 ?
N3 C4 1.269(5) . ?
N1 C1 1.324(5) . ?
N1 N2 1.359(4) . ?
N4 C6 1.329(5) . ?
N4 N5 1.348(4) . ?
N2 C3 1.356(5) . ?
N2 C4 1.409(5) . ?
N5 C8 1.340(5) . ?
C4 C5 1.483(5) . ?
C2 C3 1.360(6) . ?
C2 C1 1.414(6) . ?
C7 C8 1.359(6) . ?
C7 C6 1.391(6) . ?
B1 F1 1.365(6) . ?
B1 F3 1.386(5) . ?
B1 F4 1.387(6) . ?
B1 F2 1.395(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
N4 Cu1 N1 171.90(12) . . ?
N4 Cu1 N3 95.94(12) . . ?
N1 Cu1 N3 79.41(12) . . ?
N4 Cu1 Cl1 92.98(9) . . ?
N1 Cu1 Cl1 91.18(9) . . ?
N3 Cu1 Cl1 169.91(9) . . ?
N4 Cu1 Cl1 94.02(10) . 3_577 ?
N1 Cu1 Cl1 92.71(9) . 3_577 ?
N3 Cu1 Cl1 91.16(9) . 3_577 ?
Cl1 Cu1 Cl1 92.94(3) . 3_577 ?
Cu1 Cl1 Cu1 87.06(3) . 3_577 ?
C4 N3 Cu1 116.5(3) . . ?
C1 N1 N2 106.1(3) . . ?
C1 N1 Cu1 141.3(3) . . ?
N2 N1 Cu1 111.5(2) . . ?
C6 N4 N5 104.8(3) . . ?
C6 N4 Cu1 130.8(3) . . ?
N5 N4 Cu1 124.3(2) . . ?
C3 N2 N1 111.1(3) . . ?
C3 N2 C4 132.1(3) . . ?
N1 N2 C4 116.8(3) . . ?
C8 N5 N4 111.8(3) . . ?
N3 C4 N2 114.4(3) . . ?
N3 C4 C5 128.2(4) . . ?
N2 C4 C5 117.4(3) . . ?
C3 C2 C1 105.8(4) . . ?
N1 C1 C2 110.0(4) . . ?
N2 C3 C2 107.1(4) . . ?
C8 C7 C6 105.4(4) . . ?
N4 C6 C7 110.9(4) . . ?
N5 C8 C7 107.1(4) . . ?
F1 B1 F3 109.9(4) . . ?
F1 B1 F4 109.9(4) . . ?
F3 B1 F4 110.3(4) . . ?
F1 B1 F2 110.1(4) . . ?
F3 B1 F2 109.2(3) . . ?
F4 B1 F2 107.3(4) . . ?

_refine_diff_density_max         1.234
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.128

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Cpd6
_database_code_depnum_ccdc_archive 'CCDC 2222622'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 Cl4 Cu2 N10 O8'
_chemical_formula_weight         779.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.6960(5)
_cell_length_b                   14.7680(11)
_cell_length_c                   14.4998(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.504(4)
_cell_angle_gamma                90
_cell_volume                     1431.15(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5619
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.922
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17360
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.970
_diffrn_reflns_theta_max         28.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3650
_reflns_number_gt                3212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+11.4058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3650
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1598
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.2073(7) 0.6719(3) 0.7925(3) 0.0335(9) Uani 1 1 d . . . . .
Cu1 Cu 0.98916(8) 0.55462(4) 0.89185(4) 0.01532(16) Uani 1 1 d . . . . .
Cl2 Cl 1.25300(16) 0.65818(8) 0.69774(8) 0.0202(2) Uani 1 1 d . . . . .
Cl1 Cl 1.23630(16) 0.56730(7) 1.00512(7) 0.0182(2) Uani 1 1 d . . . . .
N1 N 1.1293(6) 0.4542(3) 0.8328(3) 0.0162(7) Uani 1 1 d . . . . .
N3 N 0.7906(6) 0.5241(3) 0.7868(3) 0.0188(8) Uani 1 1 d . . . . .
H3 H 0.683234 0.555216 0.775828 0.023 Uiso 1 1 calc R U . . .
N2 N 1.0160(6) 0.4159(3) 0.7621(3) 0.0174(7) Uani 1 1 d . . . . .
N4 N 0.8434(6) 0.6596(3) 0.9372(3) 0.0159(7) Uani 1 1 d . . . . .
N5 N 0.9261(6) 0.7187(3) 1.0002(3) 0.0202(8) Uani 1 1 d . . . . .
H5 H 1.050086 0.718438 1.019658 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8317(7) 0.4569(3) 0.7379(3) 0.0177(8) Uani 1 1 d . . . . .
C2 C 1.2928(8) 0.3357(3) 0.7769(4) 0.0263(10) Uani 1 1 d . . . . .
H2 H 1.392231 0.292972 0.768787 0.032 Uiso 1 1 calc R U . . .
C3 C 1.1130(8) 0.3437(3) 0.7278(4) 0.0253(10) Uani 1 1 d . . . . .
H3A H 1.065505 0.306482 0.679577 0.030 Uiso 1 1 calc R U . . .
C1 C 1.2949(7) 0.4062(3) 0.8425(3) 0.0215(9) Uani 1 1 d . . . . .
H1 H 1.398935 0.417331 0.886518 0.026 Uiso 1 1 calc R U . . .
O2 O 1.2378(6) 0.7431(3) 0.6493(3) 0.0332(9) Uani 1 1 d . . . . .
O1 O 1.1175(7) 0.5945(3) 0.6546(3) 0.0364(10) Uani 1 1 d . . . . .
O4 O 1.4570(6) 0.6257(3) 0.6946(3) 0.0401(11) Uani 1 1 d . . . . .
C5 C 0.7080(8) 0.4188(4) 0.6573(3) 0.0245(10) Uani 1 1 d . . . . .
H5A H 0.570101 0.437977 0.660964 0.029 Uiso 1 1 calc R U . . .
H5B H 0.711285 0.353216 0.660267 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7843(11) 0.4499(4) 0.5655(4) 0.0390(14) Uani 1 1 d . . . . .
H6A H 0.920733 0.431000 0.561670 0.059 Uiso 1 1 calc R U . . .
H6B H 0.776609 0.514667 0.561402 0.059 Uiso 1 1 calc R U . . .
H6C H 0.703498 0.423452 0.515491 0.059 Uiso 1 1 calc R U . . .
C7 C 0.6504(7) 0.6838(3) 0.9257(3) 0.0198(9) Uani 1 1 d . . . . .
H7 H 0.555316 0.655172 0.886344 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6137(8) 0.7579(4) 0.9812(3) 0.0256(10) Uani 1 1 d . . . . .
H8 H 0.492804 0.788159 0.985399 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7908(8) 0.7772(3) 1.0282(4) 0.0257(10) Uani 1 1 d . . . . .
H9 H 0.813236 0.822784 1.071800 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 Cl2 1.440(4) . ?
O3 Cu1 2.732(4) . ?
Cu1 N4 1.967(4) . ?
Cu1 N1 1.978(4) . ?
Cu1 N3 2.011(4) . ?
Cu1 Cl1 2.2669(11) . ?
Cl2 O1 1.425(4) . ?
Cl2 O2 1.437(4) . ?
Cl2 O4 1.451(4) . ?
N1 C1 1.316(6) . ?
N1 N2 1.361(5) . ?
N3 C4 1.259(6) . ?
N3 H3 0.8600 . ?
N2 C3 1.358(6) . ?
N2 C4 1.401(6) . ?
N4 C7 1.341(6) . ?
N4 N5 1.357(5) . ?
N5 C9 1.333(6) . ?
N5 H5 0.8600 . ?
C4 C5 1.500(6) . ?
C2 C3 1.366(8) . ?
C2 C1 1.411(7) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?
C1 H1 0.9300 . ?
C5 C6 1.526(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.390(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(8) . ?
C8 H8 0.9300 . ?
C9 H9 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
Cl2 O3 Cu1 124.5(2) . . ?
N4 Cu1 N1 173.89(15) . . ?
N4 Cu1 N3 96.41(16) . . ?
N1 Cu1 N3 79.24(16) . . ?
N4 Cu1 Cl1 92.73(11) . . ?
N1 Cu1 Cl1 91.76(11) . . ?
N3 Cu1 Cl1 170.71(12) . . ?
N4 Cu1 O3 88.21(14) . . ?
N1 Cu1 O3 87.94(15) . . ?
N3 Cu1 O3 95.32(15) . . ?
Cl1 Cu1 O3 86.53(9) . . ?
O1 Cl2 O2 109.7(3) . . ?
O1 Cl2 O3 110.2(3) . . ?
O2 Cl2 O3 109.3(3) . . ?
O1 Cl2 O4 110.1(3) . . ?
O2 Cl2 O4 108.2(3) . . ?
O3 Cl2 O4 109.3(3) . . ?
C1 N1 N2 106.5(4) . . ?
C1 N1 Cu1 140.9(3) . . ?
N2 N1 Cu1 112.3(3) . . ?
C4 N3 Cu1 116.5(3) . . ?
C4 N3 H3 121.8 . . ?
Cu1 N3 H3 121.8 . . ?
C3 N2 N1 110.2(4) . . ?
C3 N2 C4 132.9(4) . . ?
N1 N2 C4 116.8(4) . . ?
C7 N4 N5 105.3(4) . . ?
C7 N4 Cu1 131.4(3) . . ?
N5 N4 Cu1 122.8(3) . . ?
C9 N5 N4 111.4(4) . . ?
C9 N5 H5 124.3 . . ?
N4 N5 H5 124.3 . . ?
N3 C4 N2 114.8(4) . . ?
N3 C4 C5 127.2(4) . . ?
N2 C4 C5 118.0(4) . . ?
C3 C2 C1 105.1(4) . . ?
C3 C2 H2 127.5 . . ?
C1 C2 H2 127.5 . . ?
N2 C3 C2 107.6(4) . . ?
N2 C3 H3A 126.2 . . ?
C2 C3 H3A 126.2 . . ?
N1 C1 C2 110.6(4) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C4 C5 C6 111.6(4) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 109.9(4) . . ?
N4 C7 H7 125.1 . . ?
C8 C7 H7 125.1 . . ?
C9 C8 C7 106.0(4) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
N5 C9 C8 107.5(4) . . ?
N5 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?

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
Cu1 O3 Cl2 O1 19.7(4) . . . . ?
Cu1 O3 Cl2 O2 140.3(3) . . . . ?
Cu1 O3 Cl2 O4 -101.4(3) . . . . ?
C1 N1 N2 C3 -0.1(5) . . . . ?
Cu1 N1 N2 C3 -176.0(3) . . . . ?
C1 N1 N2 C4 -178.9(4) . . . . ?
Cu1 N1 N2 C4 5.2(5) . . . . ?
C7 N4 N5 C9 0.6(5) . . . . ?
Cu1 N4 N5 C9 -172.3(3) . . . . ?
Cu1 N3 C4 N2 -2.7(5) . . . . ?
Cu1 N3 C4 C5 178.5(4) . . . . ?
C3 N2 C4 N3 179.8(5) . . . . ?
N1 N2 C4 N3 -1.7(6) . . . . ?
C3 N2 C4 C5 -1.3(8) . . . . ?
N1 N2 C4 C5 177.2(4) . . . . ?
N1 N2 C3 C2 -0.4(6) . . . . ?
C4 N2 C3 C2 178.1(5) . . . . ?
C1 C2 C3 N2 0.7(6) . . . . ?
N2 N1 C1 C2 0.6(5) . . . . ?
Cu1 N1 C1 C2 174.6(4) . . . . ?
C3 C2 C1 N1 -0.8(6) . . . . ?
N3 C4 C5 C6 100.0(6) . . . . ?
N2 C4 C5 C6 -78.7(6) . . . . ?
N5 N4 C7 C8 0.2(5) . . . . ?
Cu1 N4 C7 C8 172.3(3) . . . . ?
N4 C7 C8 C9 -1.0(6) . . . . ?
N4 N5 C9 C8 -1.3(6) . . . . ?
C7 C8 C9 N5 1.3(6) . . . . ?

_refine_diff_density_max         1.918
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.158


####################################################################### 
# 
# 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_Cpd8
_database_code_depnum_ccdc_archive 'CCDC 2222624'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;National Changhua University of Education
Taiwan
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 B2 Cu F8 N6'
_chemical_formula_weight         483.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.2314(3)
_cell_length_b                   19.6874(8)
_cell_length_c                   8.2359(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.692(3)
_cell_angle_gamma                90
_cell_volume                     957.09(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3209
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.66

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.227
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12644
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         28.742
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2472
_reflns_number_gt                1881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2471
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.3494(3) 0.58422(9) 0.5404(2) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.2058 0.5927 0.4852 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4717(4) 0.62504(10) 0.6501(3) 0.0209(4) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.02178(14) Uani 1 2 d S . P . .
N2 N 0.6907(3) 0.60142(9) 0.7368(2) 0.0217(4) Uani 1 1 d . . . . .
N1 N 0.7543(3) 0.54124(8) 0.6830(2) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.8663(4) 0.62896(12) 0.8634(3) 0.0276(5) Uani 1 1 d . . . . .
H3A H 0.8646 0.6707 0.9207 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4184(4) 0.69450(11) 0.6980(3) 0.0287(5) Uani 1 1 d . . . . .
H5A H 0.5342 0.7264 0.6842 0.034 Uiso 1 1 calc R U . . .
H5B H 0.4302 0.6944 0.8208 0.034 Uiso 1 1 calc R U . . .
C1 C 0.9671(4) 0.53203(12) 0.7775(3) 0.0282(5) Uani 1 1 d . . . . .
H1 H 1.0564 0.4940 0.7686 0.034 Uiso 1 1 calc R U . . .
C2 C 1.0441(4) 0.58583(12) 0.8928(3) 0.0314(6) Uani 1 1 d . . . . .
H2 H 1.1905 0.5910 0.9746 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1863(5) 0.72090(12) 0.5950(3) 0.0347(6) Uani 1 1 d . . . . .
H6A H 0.1755 0.7240 0.4739 0.052 Uiso 1 1 calc R U . . .
H6B H 0.1635 0.7660 0.6371 0.052 Uiso 1 1 calc R U . . .
H6C H 0.0698 0.6898 0.6074 0.052 Uiso 1 1 calc R U . . .
F4 F 0.5691(3) 0.65402(8) 0.10370(18) 0.0428(4) Uani 1 1 d . . . . .
F2 F 0.6562(3) 0.66961(7) 0.38999(18) 0.0362(4) Uani 1 1 d . . . . .
F3 F 0.9156(2) 0.62422(8) 0.2784(2) 0.0406(4) Uani 1 1 d . . . . .
F1 F 0.6071(3) 0.56272(7) 0.2770(2) 0.0449(4) Uani 1 1 d . . . . .
B1 B 0.6850(5) 0.62851(13) 0.2629(3) 0.0273(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
N3 C4 1.265(3) . ?
N3 Cu1 1.9853(18) . ?
C4 N2 1.402(3) . ?
C4 C5 1.490(3) . ?
Cu1 N1 1.9777(18) . ?
Cu1 N1 1.9777(18) 3_666 ?
Cu1 N3 1.9852(18) 3_666 ?
Cu1 F1 2.4758(14) . ?
N2 C3 1.359(3) . ?
N2 N1 1.367(2) . ?
N1 C1 1.317(3) . ?
C3 C2 1.355(3) . ?
C5 C6 1.515(3) . ?
C1 C2 1.401(3) . ?
F4 B1 1.374(3) . ?
F2 B1 1.379(3) . ?
F3 B1 1.404(3) . ?
F1 B1 1.401(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
C4 N3 Cu1 116.18(16) . . ?
N3 C4 N2 114.73(19) . . ?
N3 C4 C5 129.6(2) . . ?
N2 C4 C5 115.65(19) . . ?
N1 Cu1 N1 180.0 . 3_666 ?
N1 Cu1 N3 99.45(8) . 3_666 ?
N1 Cu1 N3 80.55(7) 3_666 3_666 ?
N1 Cu1 N3 80.55(7) . . ?
N1 Cu1 N3 99.45(7) 3_666 . ?
N3 Cu1 N3 180.0 3_666 . ?
N1 Cu1 F1 91.14(7) . . ?
N1 Cu1 F1 88.86(7) 3_666 . ?
N3 Cu1 F1 92.17(6) 3_666 . ?
N3 Cu1 F1 87.83(6) . . ?
C3 N2 N1 110.41(19) . . ?
C3 N2 C4 132.19(19) . . ?
N1 N2 C4 117.29(17) . . ?
C1 N1 N2 105.62(18) . . ?
C1 N1 Cu1 143.40(15) . . ?
N2 N1 Cu1 110.97(13) . . ?
N2 C3 C2 107.4(2) . . ?
C4 C5 C6 114.8(2) . . ?
N1 C1 C2 111.0(2) . . ?
C3 C2 C1 105.7(2) . . ?
B1 F1 Cu1 134.86(14) . . ?
F2 B1 F4 110.7(2) . . ?
F2 B1 F1 110.3(2) . . ?
F4 B1 F1 109.1(2) . . ?
F2 B1 F3 110.2(2) . . ?
F4 B1 F3 108.6(2) . . ?
F1 B1 F3 108.0(2) . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3


