# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2388292'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cl4 Cu N6 O8'
_chemical_formula_weight         549.61

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'
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'
O O 0.0106 0.0060 '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'

_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                   7.0595(2)
_cell_length_b                   7.7575(2)
_cell_length_c                   9.7194(3)
_cell_angle_alpha                81.015(2)
_cell_angle_beta                 84.024(2)
_cell_angle_gamma                68.617(2)
_cell_volume                     488.91(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3333
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.54

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.716
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_T_max  0.837
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            7716
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2501
_reflns_number_gt                2209
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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+0.0800P] 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         2501
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.880
_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
O1 O 0.2428(3) 1.2507(2) 0.34833(17) 0.0339(4) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 1.000000 0.500000 0.01805(14) Uani 1 2 d S . P . .
Cl2 Cl 0.18349(8) 1.24717(7) 0.21081(5) 0.02059(15) Uani 1 1 d . . . . .
Cl1 Cl 0.18880(8) 0.68745(8) 0.47686(6) 0.02666(16) Uani 1 1 d . . . . .
C2 C 0.4698(4) 0.6009(3) 0.2523(2) 0.0247(5) Uani 1 1 d . . . . .
H2 H 0.422781 0.516592 0.217498 0.030 Uiso 1 1 calc R U . . .
N1 N 0.4952(3) 0.8006(2) 0.39037(17) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.3915(3) 0.6957(3) 0.3699(2) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.6273(3) 0.6567(3) 0.1997(2) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.711550 0.619812 0.118757 0.028 Uiso 1 1 calc R U . . .
N3 N 0.7182(3) 1.0021(2) 0.35754(18) 0.0201(4) Uani 1 1 d . . . . .
H3A H 0.785494 1.078124 0.356249 0.024 Uiso 1 1 calc R U . . .
N2 N 0.6420(3) 0.7745(2) 0.28387(18) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.7586(3) 0.8899(3) 0.2673(2) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.9084(4) 0.8698(4) 0.1479(2) 0.0275(5) Uani 1 1 d . . . . .
H5A H 0.992492 0.944265 0.154524 0.041 Uiso 1 1 calc R U . . .
H5B H 0.836856 0.913404 0.060875 0.041 Uiso 1 1 calc R U . . .
H5C H 0.995513 0.738183 0.148958 0.041 Uiso 1 1 calc R U . . .
O2 O 0.1727(3) 1.4179(3) 0.12468(19) 0.0383(4) Uani 1 1 d . . . . .
O4 O -0.0159(3) 1.2341(3) 0.2205(2) 0.0475(5) Uani 1 1 d . . . . .
O3 O 0.3269(3) 1.0932(3) 0.1490(2) 0.0461(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
O1 Cl2 1.4486(16) . ?
O1 Cu1 2.5178(16) . ?
Cu1 N3 1.9638(18) . ?
Cu1 N3 1.9638(18) 2_676 ?
Cu1 N1 2.0221(17) . ?
Cu1 N1 2.0221(17) 2_676 ?
Cl2 O3 1.4238(18) . ?
Cl2 O2 1.4333(18) . ?
Cl2 O4 1.440(2) . ?
Cl1 C1 1.694(2) . ?
C2 C3 1.360(3) . ?
C2 C1 1.410(3) . ?
C2 H2 0.9500 . ?
N1 C1 1.324(3) . ?
N1 N2 1.369(2) . ?
C3 N2 1.355(3) . ?
C3 H3 0.9500 . ?
N3 C4 1.270(3) . ?
N3 H3A 0.8800 . ?
N2 C4 1.403(3) . ?
C4 C5 1.473(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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 O1 Cu1 129.41(10) . . ?
N3 Cu1 N3 180.0 . 2_676 ?
N3 Cu1 N1 79.92(7) . . ?
N3 Cu1 N1 100.08(7) 2_676 . ?
N3 Cu1 N1 100.08(7) . 2_676 ?
N3 Cu1 N1 79.92(7) 2_676 2_676 ?
N1 Cu1 N1 180.0 . 2_676 ?
N3 Cu1 O1 90.48(7) . . ?
N3 Cu1 O1 89.52(7) 2_676 . ?
N1 Cu1 O1 91.53(6) . . ?
N1 Cu1 O1 88.46(6) 2_676 . ?
O3 Cl2 O2 109.62(13) . . ?
O3 Cl2 O4 109.84(14) . . ?
O2 Cl2 O4 107.72(13) . . ?
O3 Cl2 O1 110.44(10) . . ?
O2 Cl2 O1 109.33(11) . . ?
O4 Cl2 O1 109.84(12) . . ?
C3 C2 C1 104.8(2) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
C1 N1 N2 104.24(16) . . ?
C1 N1 Cu1 144.64(15) . . ?
N2 N1 Cu1 110.55(12) . . ?
N1 C1 C2 111.9(2) . . ?
N1 C1 Cl1 121.00(17) . . ?
C2 C1 Cl1 127.04(17) . . ?
N2 C3 C2 107.4(2) . . ?
N2 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C4 N3 Cu1 117.61(15) . . ?
C4 N3 H3A 121.2 . . ?
Cu1 N3 H3A 121.2 . . ?
C3 N2 N1 111.62(17) . . ?
C3 N2 C4 130.69(18) . . ?
N1 N2 C4 116.91(16) . . ?
N3 C4 N2 114.97(19) . . ?
N3 C4 C5 128.0(2) . . ?
N2 C4 C5 117.05(18) . . ?
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 . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.567
_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_2d'
_database_code_depnum_ccdc_archive 'CCDC 2388304'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 Cl2 Cu N8 O8'
_chemical_formula_weight         590.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.6343(3)
_cell_length_b                   8.8087(3)
_cell_length_c                   9.9056(3)
_cell_angle_alpha                65.897(3)
_cell_angle_beta                 88.662(2)
_cell_angle_gamma                63.858(3)
_cell_volume                     605.98(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5238
_cell_measurement_theta_max      74.1870
_cell_measurement_theta_min      4.9660

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             303
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.832
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86499
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7079
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.983
_diffrn_reflns_theta_max         74.320
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2325
_reflns_number_gt                2252
_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_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0417P)²+0.4269P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0057(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2325
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
O4 O 1.21991(18) -0.03182(18) 0.82354(14) 0.0336(3) Uani 1 1 d . . . . .
O3 O 1.34257(18) -0.0907(2) 0.62341(17) 0.0376(3) Uani 1 1 d . . . . .
O2 O 1.09552(17) -0.13225(17) 0.69011(15) 0.0306(3) Uani 1 1 d . . . . .
Cl1 Cl 1.18280(5) -0.02229(5) 0.67784(4) 0.02251(13) Uani 1 1 d . . . . .
O1 O 1.06797(16) 0.17357(16) 0.57428(14) 0.0275(3) Uani 1 1 d . . . . .
C2 C 0.7910(2) 0.5494(3) 0.8787(2) 0.0276(4) Uani 1 1 d . . . . .
C3 C 0.9126(2) 0.3620(3) 0.9358(2) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.936746 0.269402 1.036759 0.036 Uiso 1 1 calc R U . . .
C1 C 0.8042(2) 0.6253(3) 0.7273(2) 0.0270(4) Uani 1 1 d . . . . .
H1 H 0.735943 0.754041 0.657181 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6716(3) 0.6500(3) 0.9606(2) 0.0420(5) Uani 1 1 d . . . . .
H4A H 0.736607 0.606165 1.060145 0.063 Uiso 1 1 calc R U . . .
H4B H 0.571944 0.623308 0.972393 0.063 Uiso 1 1 calc R U . . .
H4C H 0.628270 0.786163 0.902793 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6050(2) 0.7272(2) 0.3669(2) 0.0253(4) Uani 1 1 d . . . . .
H5 H 0.588020 0.836674 0.375644 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4734(2) 0.7113(2) 0.30367(19) 0.0250(4) Uani 1 1 d . . . . .
C7 C 0.5548(2) 0.5309(3) 0.31742(19) 0.0258(4) Uani 1 1 d . . . . .
H7 H 0.501147 0.473380 0.286733 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2858(3) 0.8584(3) 0.2364(3) 0.0396(5) Uani 1 1 d . . . . .
H8A H 0.210206 0.798118 0.259954 0.059 Uiso 1 1 calc R U . . .
H8B H 0.272746 0.924150 0.126902 0.059 Uiso 1 1 calc R U . . .
H8C H 0.251732 0.949366 0.278488 0.059 Uiso 1 1 calc R U . . .
Cu1 Cu 1.000000 0.500000 0.500000 0.01881(12) Uani 1 2 d S . P . .
N2 N 0.99133(19) 0.3326(2) 0.82381(16) 0.0256(3) Uani 1 1 d . . . . .
H2 H 1.074972 0.222998 0.833873 0.031 Uiso 1 1 calc R U . . .
N1 N 0.92557(18) 0.4928(2) 0.69422(15) 0.0222(3) Uani 1 1 d . . . . .
N3 N 0.75746(18) 0.56897(19) 0.41347(15) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.72409(19) 0.4499(2) 0.38204(16) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.802898 0.334184 0.401340 0.028 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
O4 Cl1 1.4463(13) . ?
O3 Cl1 1.4336(13) . ?
O2 Cl1 1.4365(13) . ?
Cl1 O1 1.4514(12) . ?
O1 Cu1 2.4411(11) . ?
C2 C3 1.373(3) . ?
C2 C1 1.396(2) . ?
C2 C4 1.500(3) . ?
C3 N2 1.343(2) . ?
C3 H3 0.9500 . ?
C1 N1 1.337(2) . ?
C1 H1 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N3 1.332(2) . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(3) . ?
C6 C8 1.497(2) . ?
C7 N4 1.344(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
Cu1 N1 1.9993(14) 2_766 ?
Cu1 N1 1.9993(14) . ?
Cu1 N3 2.0066(14) . ?
Cu1 N3 2.0067(14) 2_766 ?
N2 N1 1.3453(19) . ?
N2 H2 0.8800 . ?
N3 N4 1.3480(19) . ?
N4 H4 0.8800 . ?

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
O3 Cl1 O2 110.26(8) . . ?
O3 Cl1 O4 110.20(9) . . ?
O2 Cl1 O4 109.49(8) . . ?
O3 Cl1 O1 109.38(8) . . ?
O2 Cl1 O1 109.38(8) . . ?
O4 Cl1 O1 108.09(7) . . ?
Cl1 O1 Cu1 145.03(7) . . ?
C3 C2 C1 104.38(16) . . ?
C3 C2 C4 127.80(17) . . ?
C1 C2 C4 127.82(18) . . ?
N2 C3 C2 107.97(16) . . ?
N2 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
N1 C1 C2 111.00(16) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C6 111.29(15) . . ?
N3 C5 H5 124.4 . . ?
C6 C5 H5 124.4 . . ?
C7 C6 C5 104.37(15) . . ?
C7 C6 C8 128.02(17) . . ?
C5 C6 C8 127.61(17) . . ?
N4 C7 C6 107.80(15) . . ?
N4 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 Cu1 N1 180.0 2_766 . ?
N1 Cu1 N3 89.47(6) 2_766 . ?
N1 Cu1 N3 90.53(6) . . ?
N1 Cu1 N3 90.53(6) 2_766 2_766 ?
N1 Cu1 N3 89.47(6) . 2_766 ?
N3 Cu1 N3 180.00(8) . 2_766 ?
N1 Cu1 O1 87.12(5) 2_766 . ?
N1 Cu1 O1 92.88(5) . . ?
N3 Cu1 O1 85.96(5) . . ?
N3 Cu1 O1 94.04(5) 2_766 . ?
C3 N2 N1 111.12(14) . . ?
C3 N2 H2 124.4 . . ?
N1 N2 H2 124.4 . . ?
C1 N1 N2 105.53(14) . . ?
C1 N1 Cu1 131.94(12) . . ?
N2 N1 Cu1 122.42(11) . . ?
C5 N3 N4 105.31(13) . . ?
C5 N3 Cu1 132.54(12) . . ?
N4 N3 Cu1 122.03(11) . . ?
C7 N4 N3 111.22(14) . . ?
C7 N4 H4 124.4 . . ?
N3 N4 H4 124.4 . . ?

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
O3 Cl1 O1 Cu1 -82.67(15) . . . . ?
O2 Cl1 O1 Cu1 156.47(12) . . . . ?
O4 Cl1 O1 Cu1 37.32(16) . . . . ?
C1 C2 C3 N2 0.3(2) . . . . ?
C4 C2 C3 N2 -179.46(19) . . . . ?
C3 C2 C1 N1 0.1(2) . . . . ?
C4 C2 C1 N1 179.87(18) . . . . ?
N3 C5 C6 C7 1.2(2) . . . . ?
N3 C5 C6 C8 -178.91(18) . . . . ?
C5 C6 C7 N4 -1.17(19) . . . . ?
C8 C6 C7 N4 178.94(18) . . . . ?
C2 C3 N2 N1 -0.6(2) . . . . ?
C2 C1 N1 N2 -0.5(2) . . . . ?
C2 C1 N1 Cu1 175.69(12) . . . . ?
C3 N2 N1 C1 0.67(19) . . . . ?
C3 N2 N1 Cu1 -175.96(12) . . . . ?
C6 C5 N3 N4 -0.73(19) . . . . ?
C6 C5 N3 Cu1 175.22(12) . . . . ?
C6 C7 N4 N3 0.80(19) . . . . ?
C5 N3 N4 C7 -0.05(18) . . . . ?
Cu1 N3 N4 C7 -176.52(11) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 2388302'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H48 Cl2 Cu N8 O8'
_chemical_formula_weight         759.19

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'
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'
O O 0.0106 0.0060 '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                   11.8424(9)
_cell_length_b                   23.1795(19)
_cell_length_c                   13.7638(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.605(7)
_cell_angle_gamma                90
_cell_volume                     3766.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1700
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      20.21

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.776
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            2815
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         18.499
_diffrn_reflns_theta_full        18.499
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2815
_reflns_number_gt                1907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.6744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C22 C 0.6742(8) 0.3264(4) 0.4798(6) 0.0206(17) Uani 1 1 d . . . . .
H22 H 0.748381 0.334379 0.461719 0.025 Uiso 1 1 d R U . . .
N7 N 0.6514(6) 0.2884(3) 0.5470(5) 0.0206(17) Uani 1 1 d . . . . .
N8 N 0.5362(6) 0.2909(3) 0.5481(5) 0.023(2) Uani 1 1 d . . . . .
H8 H 0.496896 0.269289 0.585723 0.028 Uiso 1 1 d R U . . .
C24 C 0.4888(8) 0.3293(4) 0.4862(7) 0.021(3) Uani 1 1 d . . . . .
C23 C 0.5767(8) 0.3527(4) 0.4407(7) 0.026(3) Uani 1 1 d . . . . .
H23 H 0.572125 0.381363 0.391129 0.031 Uiso 1 1 d R U . . .
N1 N 0.8316(6) 0.2074(3) 0.5610(5) 0.0226(14) Uani 1 1 d . . . . .
C1 C 0.7994(8) 0.1663(4) 0.4987(6) 0.0226(14) Uani 1 1 d . . . . .
H1 H 0.723090 0.161397 0.473194 0.027 Uiso 1 1 d R U . . .
C2 C 0.8874(7) 0.1318(4) 0.4744(6) 0.0226(14) Uani 1 1 d . . . . .
H2 H 0.883527 0.100257 0.430232 0.027 Uiso 1 1 d R U . . .
C3 C 0.9819(8) 0.1534(4) 0.5282(6) 0.019(2) Uani 1 1 d . . . . .
N2 N 0.9449(6) 0.1980(3) 0.5788(5) 0.020(2) Uani 1 1 d . . . . .
H2 H 0.989489 0.219090 0.618860 0.024 Uiso 1 1 d R U . . .
N3 N 0.8190(6) 0.2032(3) 0.7602(5) 0.020(2) Uani 1 1 d . . . . .
C8 C 0.9001(9) 0.2138(4) 0.8308(7) 0.022(2) Uani 1 1 d . . . . .
H8A H 0.922570 0.251440 0.851582 0.027 Uiso 1 1 d R U . . .
C9 C 0.9475(8) 0.1635(5) 0.8707(7) 0.025(3) Uani 1 1 d . . . . .
H9 H 1.006041 0.160266 0.921768 0.030 Uiso 1 1 d R U . . .
C10 C 0.8925(8) 0.1197(4) 0.8203(7) 0.019(2) Uani 1 1 d . . . . .
N4 N 0.8173(6) 0.1445(3) 0.7550(5) 0.022(2) Uani 1 1 d . . . . .
H4 H 0.771793 0.124996 0.713410 0.026 Uiso 1 1 d R U . . .
N5 N 0.6756(7) 0.3002(3) 0.7481(5) 0.022(2) Uani 1 1 d . . . . .
C15 C 0.5896(9) 0.2913(4) 0.8035(7) 0.025(3) Uani 1 1 d . . . . .
H15 H 0.562388 0.254341 0.820246 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5453(8) 0.3433(5) 0.8335(7) 0.025(3) Uani 1 1 d . . . . .
H16 H 0.485902 0.347993 0.875297 0.030 Uiso 1 1 d R U . . .
C17 C 0.6027(9) 0.3855(4) 0.7920(7) 0.027(3) Uani 1 1 d . . . . .
N6 N 0.6814(7) 0.3591(4) 0.7413(5) 0.027(2) Uani 1 1 d . . . . .
H6 H 0.730335 0.377649 0.707981 0.033 Uiso 1 1 d R U . . .
Cu1 Cu 0.74637(9) 0.25071(5) 0.65361(8) 0.0220(4) Uani 1 1 d . . . . .
Cl2 Cl 0.5218(2) 0.13553(11) 0.6406(2) 0.0322(8) Uani 1 1 d . . . . .
Cl1 Cl 0.9883(2) 0.35022(11) 0.6705(2) 0.0331(8) Uani 1 1 d . . . . .
O4 O 1.0439(5) 0.3828(3) 0.6018(4) 0.0382(19) Uani 1 1 d . . . . .
O8 O 0.4591(5) 0.1128(3) 0.7139(5) 0.0392(18) Uani 1 1 d . . . . .
O2 O 1.0484(5) 0.2956(3) 0.6892(5) 0.050(2) Uani 1 1 d . . . . .
O3 O 0.9838(6) 0.3803(3) 0.7593(5) 0.051(2) Uani 1 1 d . . . . .
O1 O 0.8750(5) 0.3359(3) 0.6306(5) 0.051(2) Uani 1 1 d . . . . .
O5 O 0.5661(6) 0.1906(3) 0.6697(5) 0.062(2) Uani 1 1 d . . . . .
O7 O 0.6208(6) 0.0972(3) 0.6335(5) 0.060(2) Uani 1 1 d . . . . .
O6 O 0.4590(6) 0.1364(3) 0.5490(5) 0.057(2) Uani 1 1 d . . . . .
C11 C 0.8990(7) 0.0546(4) 0.8283(7) 0.022(3) Uani 1 1 d . . . . .
C4 C 1.1063(8) 0.1366(4) 0.5347(7) 0.027(3) Uani 1 1 d . . . . .
C25 C 0.3618(8) 0.3369(5) 0.4732(7) 0.035(3) Uani 1 1 d . . . . .
C13 C 1.0201(8) 0.0389(4) 0.8704(7) 0.041(3) Uani 1 1 d . . . . .
H13A H 1.037133 0.058435 0.933049 0.062 Uiso 1 1 d R U . . .
H13B H 1.025583 -0.002925 0.879849 0.062 Uiso 1 1 d R U . . .
H13C H 1.074563 0.051205 0.824549 0.062 Uiso 1 1 d R U . . .
C18 C 0.5928(12) 0.4512(5) 0.7955(11) 0.083(3) Uani 1 1 d . . . . .
C7 C 1.1595(8) 0.1466(4) 0.6361(7) 0.046(3) Uani 1 1 d . . . . .
H7A H 1.118716 0.124281 0.682630 0.069 Uiso 1 1 d R U . . .
H7B H 1.238936 0.134411 0.639960 0.069 Uiso 1 1 d R U . . .
H7C H 1.155436 0.187761 0.652020 0.069 Uiso 1 1 d R U . . .
C12 C 0.8180(8) 0.0334(4) 0.9015(7) 0.048(3) Uani 1 1 d . . . . .
H12A H 0.739894 0.042385 0.877403 0.072 Uiso 1 1 d R U . . .
H12B H 0.826363 -0.008395 0.909963 0.072 Uiso 1 1 d R U . . .
H12C H 0.835884 0.052655 0.964293 0.072 Uiso 1 1 d R U . . .
C5 C 1.1664(8) 0.1742(5) 0.4624(7) 0.051(3) Uani 1 1 d . . . . .
H5A H 1.154976 0.215009 0.477218 0.076 Uiso 1 1 d R U . . .
H5B H 1.247646 0.165479 0.467928 0.076 Uiso 1 1 d R U . . .
H5C H 1.134666 0.165959 0.395868 0.076 Uiso 1 1 d R U . . .
C6 C 1.1172(8) 0.0735(4) 0.5050(8) 0.056(3) Uani 1 1 d . . . . .
H6A H 1.085434 0.068543 0.437492 0.084 Uiso 1 1 d R U . . .
H6B H 1.197394 0.062583 0.510012 0.084 Uiso 1 1 d R U . . .
H6C H 1.076034 0.048823 0.547974 0.084 Uiso 1 1 d R U . . .
C26 C 0.3146(8) 0.3030(5) 0.3838(7) 0.049(3) Uani 1 1 d . . . . .
H26A H 0.330711 0.261907 0.393825 0.074 Uiso 1 1 d R U . . .
H26B H 0.232491 0.308867 0.374075 0.074 Uiso 1 1 d R U . . .
H26C H 0.350291 0.316557 0.326135 0.074 Uiso 1 1 d R U . . .
C14 C 0.8745(9) 0.0256(4) 0.7311(7) 0.047(3) Uani 1 1 d . . . . .
H14A H 0.923400 0.042070 0.684023 0.071 Uiso 1 1 d R U . . .
H14B H 0.889340 -0.015890 0.737714 0.071 Uiso 1 1 d R U . . .
H14C H 0.794980 0.031750 0.708124 0.071 Uiso 1 1 d R U . . .
C28 C 0.3072(8) 0.3169(5) 0.5634(7) 0.056(3) Uani 1 1 d . . . . .
H28A H 0.336430 0.339782 0.619792 0.083 Uiso 1 1 d R U . . .
H28B H 0.224870 0.321692 0.553442 0.083 Uiso 1 1 d R U . . .
H28C H 0.325200 0.276092 0.575131 0.083 Uiso 1 1 d R U . . .
C27 C 0.3375(9) 0.4017(5) 0.4552(8) 0.069(4) Uani 1 1 d . . . . .
H27A H 0.367277 0.413451 0.393766 0.104 Uiso 1 1 d R U . . .
H27B H 0.255637 0.408521 0.451496 0.104 Uiso 1 1 d R U . . .
H27C H 0.374517 0.424211 0.508956 0.104 Uiso 1 1 d R U . . .
C21 C 0.5983(11) 0.4710(4) 0.8976(8) 0.085(5) Uani 1 1 d . . . . .
H21A H 0.532548 0.455504 0.927794 0.127 Uiso 1 1 d R U . . .
H21B H 0.668008 0.457054 0.933174 0.127 Uiso 1 1 d R U . . .
H21C H 0.596538 0.513214 0.899644 0.127 Uiso 1 1 d R U . . .
C19 C 0.7011(10) 0.4802(4) 0.7549(9) 0.083(3) Uani 1 1 d . . . . .
H19A H 0.694670 0.522273 0.758269 0.125 Uiso 1 1 d R U . . .
H19B H 0.769739 0.467673 0.793739 0.125 Uiso 1 1 d R U . . .
H19C H 0.705549 0.468403 0.686899 0.125 Uiso 1 1 d R U . . .
C20 C 0.4978(10) 0.4698(4) 0.7272(9) 0.083(3) Uani 1 1 d . . . . .
H20A H 0.491787 0.511922 0.727654 0.125 Uiso 1 1 d R U . . .
H20B H 0.508627 0.456522 0.660964 0.125 Uiso 1 1 d R U . . .
H20C H 0.428187 0.452862 0.748794 0.125 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C22 N7 1.320(10) . ?
C22 C23 1.377(11) . ?
C22 H22 0.9499 . ?
N7 N8 1.367(9) . ?
N7 Cu1 1.979(7) . ?
N8 C24 1.325(10) . ?
N8 H8 0.8800 . ?
C24 C23 1.370(12) . ?
C24 C25 1.510(12) . ?
C23 H23 0.9500 . ?
N1 C1 1.318(10) . ?
N1 N2 1.361(9) . ?
N1 Cu1 1.964(7) . ?
C1 C2 1.376(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(11) . ?
C2 H2 0.9499 . ?
C3 N2 1.341(10) . ?
C3 C4 1.519(12) . ?
N2 H2 0.8801 . ?
N3 C8 1.333(10) . ?
N3 N4 1.362(9) . ?
N3 Cu1 1.976(7) . ?
C8 C9 1.388(11) . ?
C8 H8A 0.9500 . ?
C9 C10 1.364(11) . ?
C9 H9 0.9500 . ?
C10 N4 1.342(10) . ?
C10 C11 1.515(12) . ?
N4 H4 0.8800 . ?
N5 C15 1.338(10) . ?
N5 N6 1.369(9) . ?
N5 Cu1 1.971(8) . ?
C15 C16 1.389(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.346(12) . ?
C16 H16 0.9500 . ?
C17 N6 1.355(10) . ?
C17 C18 1.527(14) . ?
N6 H6 0.8799 . ?
Cu1 O1 2.529(6) . ?
Cu1 O5 2.574(7) . ?
Cl2 O8 1.402(6) . ?
Cl2 O6 1.412(6) . ?
Cl2 O5 1.425(7) . ?
Cl2 O7 1.481(7) . ?
Cl1 O3 1.412(6) . ?
Cl1 O4 1.414(6) . ?
Cl1 O1 1.447(6) . ?
Cl1 O2 1.465(6) . ?
C11 C14 1.505(11) . ?
C11 C12 1.527(12) . ?
C11 C13 1.546(11) . ?
C4 C7 1.503(12) . ?
C4 C6 1.527(12) . ?
C4 C5 1.540(12) . ?
C25 C28 1.518(12) . ?
C25 C26 1.526(12) . ?
C25 C27 1.546(13) . ?
C13 H13A 0.9801 . ?
C13 H13B 0.9802 . ?
C13 H13C 0.9799 . ?
C18 C20 1.472(14) . ?
C18 C21 1.474(15) . ?
C18 C19 1.589(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9801 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9801 . ?
C12 H12C 0.9799 . ?
C5 H5A 0.9801 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9799 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9801 . ?
C26 H26A 0.9799 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9801 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C28 H28A 0.9802 . ?
C28 H28B 0.9799 . ?
C28 H28C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9799 . ?
C27 H27C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9798 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9801 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9799 . ?

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
N7 C22 C23 110.9(8) . . ?
N7 C22 H22 124.0 . . ?
C23 C22 H22 125.1 . . ?
C22 N7 N8 103.9(7) . . ?
C22 N7 Cu1 132.7(6) . . ?
N8 N7 Cu1 121.2(6) . . ?
C24 N8 N7 113.2(7) . . ?
C24 N8 H8 122.9 . . ?
N7 N8 H8 123.9 . . ?
N8 C24 C23 105.2(8) . . ?
N8 C24 C25 121.4(9) . . ?
C23 C24 C25 133.3(9) . . ?
C24 C23 C22 106.8(8) . . ?
C24 C23 H23 127.1 . . ?
C22 C23 H23 126.0 . . ?
C1 N1 N2 103.4(7) . . ?
C1 N1 Cu1 130.9(7) . . ?
N2 N1 Cu1 121.0(5) . . ?
N1 C1 C2 113.2(8) . . ?
N1 C1 H1 123.0 . . ?
C2 C1 H1 123.8 . . ?
C1 C2 C3 104.8(8) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 128.0 . . ?
N2 C3 C2 105.8(8) . . ?
N2 C3 C4 121.5(8) . . ?
C2 C3 C4 132.6(9) . . ?
C3 N2 N1 112.9(7) . . ?
C3 N2 H2 123.3 . . ?
N1 N2 H2 123.9 . . ?
C8 N3 N4 103.2(7) . . ?
C8 N3 Cu1 133.2(7) . . ?
N4 N3 Cu1 120.9(6) . . ?
N3 C8 C9 112.2(8) . . ?
N3 C8 H8A 123.8 . . ?
C9 C8 H8A 124.0 . . ?
C10 C9 C8 105.2(8) . . ?
C10 C9 H9 127.5 . . ?
C8 C9 H9 127.3 . . ?
N4 C10 C9 106.6(8) . . ?
N4 C10 C11 120.2(10) . . ?
C9 C10 C11 133.2(10) . . ?
C10 N4 N3 112.7(7) . . ?
C10 N4 H4 123.6 . . ?
N3 N4 H4 123.6 . . ?
C15 N5 N6 103.7(8) . . ?
C15 N5 Cu1 132.1(7) . . ?
N6 N5 Cu1 120.6(7) . . ?
N5 C15 C16 111.0(8) . . ?
N5 C15 H15 124.5 . . ?
C16 C15 H15 124.5 . . ?
C17 C16 C15 106.8(8) . . ?
C17 C16 H16 126.6 . . ?
C15 C16 H16 126.5 . . ?
C16 C17 N6 106.3(8) . . ?
C16 C17 C18 132.1(12) . . ?
N6 C17 C18 121.6(12) . . ?
C17 N6 N5 112.1(8) . . ?
C17 N6 H6 123.8 . . ?
N5 N6 H6 124.1 . . ?
N1 Cu1 N5 173.5(3) . . ?
N1 Cu1 N3 88.9(3) . . ?
N5 Cu1 N3 91.0(3) . . ?
N1 Cu1 N7 92.0(3) . . ?
N5 Cu1 N7 89.2(3) . . ?
N3 Cu1 N7 169.9(3) . . ?
N1 Cu1 O1 88.3(3) . . ?
N5 Cu1 O1 85.4(3) . . ?
N3 Cu1 O1 107.3(3) . . ?
N7 Cu1 O1 82.8(3) . . ?
N1 Cu1 O5 104.6(3) . . ?
N5 Cu1 O5 81.9(3) . . ?
N3 Cu1 O5 87.1(3) . . ?
N7 Cu1 O5 82.9(3) . . ?
O1 Cu1 O5 161.0(2) . . ?
O8 Cl2 O6 112.1(4) . . ?
O8 Cl2 O5 109.8(4) . . ?
O6 Cl2 O5 113.2(4) . . ?
O8 Cl2 O7 106.8(4) . . ?
O6 Cl2 O7 108.2(4) . . ?
O5 Cl2 O7 106.2(4) . . ?
O3 Cl1 O4 111.5(4) . . ?
O3 Cl1 O1 110.2(4) . . ?
O4 Cl1 O1 109.7(4) . . ?
O3 Cl1 O2 109.1(4) . . ?
O4 Cl1 O2 109.4(4) . . ?
O1 Cl1 O2 106.9(4) . . ?
Cl1 O1 Cu1 132.9(4) . . ?
Cl2 O5 Cu1 138.6(5) . . ?
C14 C11 C10 112.1(8) . . ?
C14 C11 C12 110.9(8) . . ?
C10 C11 C12 109.7(8) . . ?
C14 C11 C13 109.6(7) . . ?
C10 C11 C13 107.6(8) . . ?
C12 C11 C13 106.9(7) . . ?
C7 C4 C3 110.3(8) . . ?
C7 C4 C6 111.1(8) . . ?
C3 C4 C6 109.4(8) . . ?
C7 C4 C5 109.4(8) . . ?
C3 C4 C5 108.2(7) . . ?
C6 C4 C5 108.4(8) . . ?
C24 C25 C28 110.7(8) . . ?
C24 C25 C26 109.4(8) . . ?
C28 C25 C26 110.5(8) . . ?
C24 C25 C27 107.6(9) . . ?
C28 C25 C27 110.0(9) . . ?
C26 C25 C27 108.6(8) . . ?
C11 C13 H13A 109.9 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.2 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C18 C21 119.4(12) . . ?
C20 C18 C17 109.2(10) . . ?
C21 C18 C17 110.0(10) . . ?
C20 C18 C19 104.4(11) . . ?
C21 C18 C19 103.2(10) . . ?
C17 C18 C19 110.2(11) . . ?
C4 C7 H7A 109.4 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.4 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.4 . . ?
C4 C6 H6B 109.3 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.8 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C25 C26 H26A 109.3 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 C14 H14A 109.4 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C25 C28 H28A 109.7 . . ?
C25 C28 H28B 109.6 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.1 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.6 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.3 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C18 C21 H21A 108.4 . . ?
C18 C21 H21B 110.2 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.9 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 108.9 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.9 . . ?
C18 C20 H20B 110.6 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 107.9 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 C22 N7 N8 0.8(9) . . . . ?
C23 C22 N7 Cu1 -161.7(6) . . . . ?
C22 N7 N8 C24 -1.1(9) . . . . ?
Cu1 N7 N8 C24 163.9(5) . . . . ?
N7 N8 C24 C23 0.9(10) . . . . ?
N7 N8 C24 C25 177.3(8) . . . . ?
N8 C24 C23 C22 -0.4(10) . . . . ?
C25 C24 C23 C22 -176.1(10) . . . . ?
N7 C22 C23 C24 -0.2(10) . . . . ?
N2 N1 C1 C2 -1.3(9) . . . . ?
Cu1 N1 C1 C2 -156.3(6) . . . . ?
N1 C1 C2 C3 1.1(10) . . . . ?
C1 C2 C3 N2 -0.3(9) . . . . ?
C1 C2 C3 C4 -178.6(9) . . . . ?
C2 C3 N2 N1 -0.4(9) . . . . ?
C4 C3 N2 N1 178.1(7) . . . . ?
C1 N1 N2 C3 1.1(9) . . . . ?
Cu1 N1 N2 C3 159.1(5) . . . . ?
N4 N3 C8 C9 -0.9(9) . . . . ?
Cu1 N3 C8 C9 -161.7(6) . . . . ?
N3 C8 C9 C10 0.6(10) . . . . ?
C8 C9 C10 N4 -0.1(10) . . . . ?
C8 C9 C10 C11 -177.5(9) . . . . ?
C9 C10 N4 N3 -0.5(10) . . . . ?
C11 C10 N4 N3 177.3(8) . . . . ?
C8 N3 N4 C10 0.9(9) . . . . ?
Cu1 N3 N4 C10 164.7(6) . . . . ?
N6 N5 C15 C16 -2.1(9) . . . . ?
Cu1 N5 C15 C16 -160.0(6) . . . . ?
N5 C15 C16 C17 2.5(10) . . . . ?
C15 C16 C17 N6 -1.8(10) . . . . ?
C15 C16 C17 C18 179.0(10) . . . . ?
C16 C17 N6 N5 0.6(10) . . . . ?
C18 C17 N6 N5 179.9(8) . . . . ?
C15 N5 N6 C17 0.9(9) . . . . ?
Cu1 N5 N6 C17 162.0(6) . . . . ?
O3 Cl1 O1 Cu1 -88.1(6) . . . . ?
O4 Cl1 O1 Cu1 148.8(5) . . . . ?
O2 Cl1 O1 Cu1 30.3(6) . . . . ?
O8 Cl2 O5 Cu1 143.8(5) . . . . ?
O6 Cl2 O5 Cu1 -90.0(6) . . . . ?
O7 Cl2 O5 Cu1 28.6(7) . . . . ?
N4 C10 C11 C14 34.2(12) . . . . ?
C9 C10 C11 C14 -148.6(10) . . . . ?
N4 C10 C11 C12 -89.4(10) . . . . ?
C9 C10 C11 C12 87.7(12) . . . . ?
N4 C10 C11 C13 154.7(8) . . . . ?
C9 C10 C11 C13 -28.2(14) . . . . ?
N2 C3 C4 C7 35.1(12) . . . . ?
C2 C3 C4 C7 -146.9(9) . . . . ?
N2 C3 C4 C6 157.6(8) . . . . ?
C2 C3 C4 C6 -24.4(14) . . . . ?
N2 C3 C4 C5 -84.5(10) . . . . ?
C2 C3 C4 C5 93.5(11) . . . . ?
N8 C24 C25 C28 24.2(13) . . . . ?
C23 C24 C25 C28 -160.6(10) . . . . ?
N8 C24 C25 C26 -97.8(10) . . . . ?
C23 C24 C25 C26 77.4(13) . . . . ?
N8 C24 C25 C27 144.4(9) . . . . ?
C23 C24 C25 C27 -40.5(14) . . . . ?
C16 C17 C18 C20 -80.0(16) . . . . ?
N6 C17 C18 C20 101.0(13) . . . . ?
C16 C17 C18 C21 52.8(16) . . . . ?
N6 C17 C18 C21 -126.3(11) . . . . ?
C16 C17 C18 C19 165.9(10) . . . . ?
N6 C17 C18 C19 -13.1(14) . . . . ?

_refine_diff_density_max         0.889
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.082


# start Validation Reply Form
_vrf_THETM01_2e                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Since the I/sigma value at 2 theta = 50 has already dropped 
          below 3, these values are theoretically considered noise.
          Thus, we truncated the data at this point, which led to the
          generation of this alert.
;
_vrf_PLAT088_2e                  
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.13 Note  
RESPONSE: This alert was caused by our truncation of signals that were noise
          , as well as the inherently poor crystal quality.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_2e'
_database_code_depnum_ccdc_archive 'CCDC 2388305'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H48 Cl2 Cu N8 O8'
_chemical_formula_weight         759.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.7271(2)
_cell_length_b                   9.8586(2)
_cell_length_c                   12.2365(3)
_cell_angle_alpha                77.454(2)
_cell_angle_beta                 85.620(2)
_cell_angle_gamma                64.130(2)
_cell_volume                     924.47(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7481
_cell_measurement_theta_max      74.7900
_cell_measurement_theta_min      3.6860

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             399
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.630
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91738
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10851
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.701
_diffrn_reflns_theta_max         74.823
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3567
_reflns_number_gt                3392
_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_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0347P)²+0.5456P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3567
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C9 C 0.91160(19) 0.09349(17) 0.65551(12) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.8021(2) 0.04167(18) 0.62299(13) 0.0261(3) Uani 1 1 d . . . . .
H10 H 0.814516 -0.061357 0.641272 0.031 Uiso 1 1 calc R U . . .
C8 C 0.83880(19) 0.25085(17) 0.60796(12) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.885252 0.319503 0.615414 0.025 Uiso 1 1 calc R U . . .
C11 C 1.06757(19) 0.00288(17) 0.73224(13) 0.0223(3) Uani 1 1 d . . . . .
C12 C 1.2058(2) 0.0574(2) 0.69354(16) 0.0350(4) Uani 1 1 d . . . . .
H12A H 1.237907 0.042483 0.617038 0.052 Uiso 1 1 calc R U . . .
H12B H 1.305821 -0.002130 0.743631 0.052 Uiso 1 1 calc R U . . .
H12C H 1.162315 0.166948 0.695143 0.052 Uiso 1 1 calc R U . . .
C13 C 1.0156(2) 0.0273(2) 0.85125(15) 0.0389(4) Uani 1 1 d . . . . .
H13A H 0.969339 0.137315 0.852039 0.058 Uiso 1 1 calc R U . . .
H13B H 1.115471 -0.029877 0.901669 0.058 Uiso 1 1 calc R U . . .
H13C H 0.928688 -0.009724 0.876276 0.058 Uiso 1 1 calc R U . . .
C14 C 1.1372(2) -0.1690(2) 0.73152(17) 0.0390(4) Uani 1 1 d . . . . .
H14A H 1.052020 -0.206138 0.761827 0.059 Uiso 1 1 calc R U . . .
H14B H 1.241611 -0.226246 0.777739 0.059 Uiso 1 1 calc R U . . .
H14C H 1.162369 -0.184446 0.654548 0.059 Uiso 1 1 calc R U . . .
C1 C 0.5569(2) 0.61682(18) 0.26080(13) 0.0250(3) Uani 1 1 d . . . . .
H1 H 0.439449 0.655973 0.242511 0.030 Uiso 1 1 calc R U . . .
C2 C 0.68136(19) 0.61762(17) 0.18281(12) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.8302(2) 0.55048(18) 0.24651(13) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.940620 0.533659 0.219326 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6609(2) 0.67107(19) 0.05675(13) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.4751(3) 0.7771(3) 0.02439(16) 0.0467(5) Uani 1 1 d . . . . .
H5A H 0.404813 0.722481 0.052568 0.070 Uiso 1 1 calc R U . . .
H5B H 0.463017 0.808433 -0.057344 0.070 Uiso 1 1 calc R U . . .
H5C H 0.438003 0.868521 0.057114 0.070 Uiso 1 1 calc R U . . .
C6 C 0.7689(3) 0.7579(3) 0.01370(17) 0.0496(5) Uani 1 1 d . . . . .
H6A H 0.732523 0.847521 0.048461 0.074 Uiso 1 1 calc R U . . .
H6B H 0.754587 0.792259 -0.067800 0.074 Uiso 1 1 calc R U . . .
H6C H 0.889083 0.689567 0.032830 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7192(3) 0.5292(3) 0.00439(17) 0.0525(6) Uani 1 1 d . . . . .
H7A H 0.840818 0.464370 0.020754 0.079 Uiso 1 1 calc R U . . .
H7B H 0.699703 0.562046 -0.076872 0.079 Uiso 1 1 calc R U . . .
H7C H 0.654319 0.470395 0.035773 0.079 Uiso 1 1 calc R U . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.02052(10) Uani 1 2 d S . P . .
N4 N 0.67545(17) 0.16174(15) 0.56124(11) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.590304 0.156073 0.531464 0.030 Uiso 1 1 calc R U . . .
N3 N 0.69470(16) 0.29261(14) 0.55036(11) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.62300(16) 0.55413(15) 0.36479(11) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.79088(16) 0.51339(15) 0.35340(11) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.865733 0.467967 0.409255 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.29000(4) 0.31349(4) 0.38450(3) 0.02071(10) Uani 1 1 d . . . . .
O4 O 0.38317(15) 0.16399(13) 0.45403(10) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.39494(15) 0.39617(13) 0.36788(10) 0.0306(3) Uani 1 1 d . . . . .
O3 O 0.13631(14) 0.39909(15) 0.43941(11) 0.0349(3) Uani 1 1 d . . . . .
O2 O 0.24682(16) 0.29702(14) 0.27914(9) 0.0330(3) 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
C9 C10 1.380(2) . ?
C9 C8 1.398(2) . ?
C9 C11 1.517(2) . ?
C10 N4 1.338(2) . ?
C10 H10 0.9500 . ?
C8 N3 1.3437(19) . ?
C8 H8 0.9500 . ?
C11 C12 1.529(2) . ?
C11 C13 1.530(2) . ?
C11 C14 1.532(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 N1 1.339(2) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(2) . ?
C2 C4 1.515(2) . ?
C3 N2 1.340(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.522(2) . ?
C4 C6 1.527(2) . ?
C4 C7 1.531(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
Cu1 N1 2.0048(13) . ?
Cu1 N1 2.0048(13) 2_666 ?
Cu1 N3 2.0070(12) 2_666 ?
Cu1 N3 2.0070(13) . ?
Cu1 O1 2.5033(11) . ?
N4 N3 1.3497(18) . ?
N4 H4 0.8800 . ?
N1 N2 1.3442(18) . ?
N2 H2 0.8800 . ?
Cl1 O2 1.4315(11) . ?
Cl1 O4 1.4396(11) . ?
Cl1 O3 1.4434(12) . ?
Cl1 O1 1.4476(11) . ?

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
C10 C9 C8 104.01(13) . . ?
C10 C9 C11 127.88(13) . . ?
C8 C9 C11 127.96(13) . . ?
N4 C10 C9 108.15(13) . . ?
N4 C10 H10 125.9 . . ?
C9 C10 H10 125.9 . . ?
N3 C8 C9 111.32(13) . . ?
N3 C8 H8 124.3 . . ?
C9 C8 H8 124.3 . . ?
C9 C11 C12 110.31(13) . . ?
C9 C11 C13 108.59(13) . . ?
C12 C11 C13 109.76(14) . . ?
C9 C11 C14 109.81(13) . . ?
C12 C11 C14 109.28(14) . . ?
C13 C11 C14 109.08(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C1 C2 111.74(14) . . ?
N1 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 103.85(13) . . ?
C3 C2 C4 127.85(14) . . ?
C1 C2 C4 128.22(14) . . ?
N2 C3 C2 107.82(13) . . ?
N2 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C2 C4 C5 110.25(14) . . ?
C2 C4 C6 110.06(14) . . ?
C5 C4 C6 109.02(16) . . ?
C2 C4 C7 108.36(14) . . ?
C5 C4 C7 109.37(17) . . ?
C6 C4 C7 109.77(17) . . ?
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 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 Cu1 N1 180.0 . 2_666 ?
N1 Cu1 N3 87.06(5) . 2_666 ?
N1 Cu1 N3 92.94(5) 2_666 2_666 ?
N1 Cu1 N3 92.94(5) . . ?
N1 Cu1 N3 87.06(5) 2_666 . ?
N3 Cu1 N3 180.0 2_666 . ?
N1 Cu1 O1 82.96(5) . . ?
N1 Cu1 O1 97.04(5) 2_666 . ?
N3 Cu1 O1 89.15(5) 2_666 . ?
N3 Cu1 O1 90.85(5) . . ?
C10 N4 N3 111.50(12) . . ?
C10 N4 H4 124.3 . . ?
N3 N4 H4 124.3 . . ?
C8 N3 N4 105.02(12) . . ?
C8 N3 Cu1 130.97(10) . . ?
N4 N3 Cu1 121.25(10) . . ?
C1 N1 N2 104.92(12) . . ?
C1 N1 Cu1 125.80(10) . . ?
N2 N1 Cu1 128.39(10) . . ?
C3 N2 N1 111.66(12) . . ?
C3 N2 H2 124.2 . . ?
N1 N2 H2 124.2 . . ?
O2 Cl1 O4 109.89(7) . . ?
O2 Cl1 O3 109.47(7) . . ?
O4 Cl1 O3 109.85(8) . . ?
O2 Cl1 O1 110.32(7) . . ?
O4 Cl1 O1 108.67(7) . . ?
O3 Cl1 O1 108.63(7) . . ?
Cl1 O1 Cu1 131.90(7) . . ?

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
C8 C9 C10 N4 -0.09(18) . . . . ?
C11 C9 C10 N4 175.84(14) . . . . ?
C10 C9 C8 N3 0.03(17) . . . . ?
C11 C9 C8 N3 -175.90(14) . . . . ?
C10 C9 C11 C12 144.95(17) . . . . ?
C8 C9 C11 C12 -40.1(2) . . . . ?
C10 C9 C11 C13 -94.7(2) . . . . ?
C8 C9 C11 C13 80.3(2) . . . . ?
C10 C9 C11 C14 24.5(2) . . . . ?
C8 C9 C11 C14 -160.55(16) . . . . ?
N1 C1 C2 C3 -0.02(18) . . . . ?
N1 C1 C2 C4 176.87(15) . . . . ?
C1 C2 C3 N2 0.50(17) . . . . ?
C4 C2 C3 N2 -176.40(15) . . . . ?
C3 C2 C4 C5 -164.16(17) . . . . ?
C1 C2 C4 C5 19.7(2) . . . . ?
C3 C2 C4 C6 -43.9(2) . . . . ?
C1 C2 C4 C6 139.97(18) . . . . ?
C3 C2 C4 C7 76.2(2) . . . . ?
C1 C2 C4 C7 -100.0(2) . . . . ?
C9 C10 N4 N3 0.13(19) . . . . ?
C9 C8 N3 N4 0.05(17) . . . . ?
C9 C8 N3 Cu1 160.85(11) . . . . ?
C10 N4 N3 C8 -0.11(17) . . . . ?
C10 N4 N3 Cu1 -163.23(11) . . . . ?
C2 C1 N1 N2 -0.46(18) . . . . ?
C2 C1 N1 Cu1 -170.38(10) . . . . ?
C2 C3 N2 N1 -0.84(18) . . . . ?
C1 N1 N2 C3 0.80(17) . . . . ?
Cu1 N1 N2 C3 170.37(11) . . . . ?
O2 Cl1 O1 Cu1 172.34(8) . . . . ?
O4 Cl1 O1 Cu1 -67.13(11) . . . . ?
O3 Cl1 O1 Cu1 52.35(11) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2388299'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl6 Cu N8 O8'
_chemical_formula_weight         672.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   31.7856(3)
_cell_length_b                   9.81790(10)
_cell_length_c                   31.0513(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.6950(10)
_cell_angle_gamma                90
_cell_volume                     9602.85(16)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32315
_cell_measurement_theta_max      74.8240
_cell_measurement_theta_min      2.8230

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             5360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.966
_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9641
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         74.912
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9641
_reflns_number_gt                8595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_refine_special_details          Twin,SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.3500P)²+0.6000P] 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         9641
_refine_ls_number_parameters     632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.3770
_refine_ls_wR_factor_gt          0.3696
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.4422(2) 0.7653(7) 0.5447(2) 0.0314(15) Uani 1 1 d . . . . .
H1 H 0.430714 0.788241 0.515808 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4356(2) 0.8349(7) 0.5815(2) 0.0312(15) Uani 1 1 d . . . . .
H2 H 0.418842 0.914046 0.583548 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4592(2) 0.7630(7) 0.6153(2) 0.0259(13) Uani 1 1 d . . . . .
C4 C 0.4294(2) 0.3533(7) 0.5822(2) 0.0245(13) Uani 1 1 d . . . . .
C5 C 0.4188(2) 0.2426(7) 0.5549(2) 0.0294(14) Uani 1 1 d . . . . .
H5 H 0.391298 0.210831 0.543721 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4572(2) 0.1902(7) 0.5480(2) 0.0297(15) Uani 1 1 d . . . . .
H6 H 0.461371 0.112719 0.530722 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5225(2) 0.2323(6) 0.6827(2) 0.0222(12) Uani 1 1 d . . . . .
C8 C 0.5555(2) 0.1521(7) 0.7024(2) 0.0283(14) Uani 1 1 d . . . . .
H8 H 0.553588 0.074434 0.720290 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5914(2) 0.2100(7) 0.6903(2) 0.0260(14) Uani 1 1 d . . . . .
H9 H 0.619687 0.179113 0.698408 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5622(2) 0.6322(6) 0.7101(2) 0.0227(12) Uani 1 1 d . . . . .
C11 C 0.5840(2) 0.7531(6) 0.7196(2) 0.0251(13) Uani 1 1 d . . . . .
H11 H 0.595187 0.786842 0.747521 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5861(2) 0.8133(7) 0.6803(2) 0.0250(13) Uani 1 1 d . . . . .
H12 H 0.600107 0.896299 0.675593 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.57468(5) 0.53788(14) 0.54816(5) 0.0203(4) Uani 1 1 d . . . . .
Cl2 Cl 0.46336(6) 0.79391(19) 0.66991(6) 0.0365(5) Uani 1 1 d . . . . .
Cl3 Cl 0.39605(6) 0.46292(19) 0.60345(7) 0.0394(5) Uani 1 1 d . . . . .
Cl4 Cl 0.46942(5) 0.21601(18) 0.68554(6) 0.0334(4) Uani 1 1 d . . . . .
Cl5 Cl 0.55251(6) 0.50992(16) 0.74620(5) 0.0281(4) Uani 1 1 d . . . . .
Cu1 Cu 0.51039(3) 0.49535(8) 0.62875(3) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.47929(17) 0.6566(5) 0.60034(17) 0.0232(11) Uani 1 1 d . . . . .
N2 N 0.46787(18) 0.6583(6) 0.55677(18) 0.0263(12) Uani 1 1 d . . . . .
H2A H 0.476065 0.597862 0.538690 0.032 Uiso 1 1 calc R U . . .
N3 N 0.47171(16) 0.3682(5) 0.59106(17) 0.0213(11) Uani 1 1 d . . . . .
N4 N 0.48784(17) 0.2664(5) 0.56966(17) 0.0230(11) Uani 1 1 d . . . . .
H4 H 0.515171 0.251595 0.569841 0.028 Uiso 1 1 calc R U . . .
N5 N 0.53658(16) 0.3333(5) 0.65985(17) 0.0202(10) Uani 1 1 d . . . . .
N6 N 0.57965(16) 0.3168(5) 0.66524(17) 0.0221(11) Uani 1 1 d . . . . .
H6A H 0.597342 0.370001 0.653602 0.027 Uiso 1 1 calc R U . . .
N7 N 0.54998(16) 0.6190(5) 0.66721(17) 0.0205(10) Uani 1 1 d . . . . .
N8 N 0.56487(17) 0.7349(5) 0.64962(17) 0.0212(10) Uani 1 1 d . . . . .
H8A H 0.560947 0.754834 0.621741 0.025 Uiso 1 1 calc R U . . .
O1 O 0.56076(15) 0.4604(4) 0.58388(15) 0.0254(10) Uani 1 1 d . . . . .
O2 O 0.54035(16) 0.5383(5) 0.51272(16) 0.0320(11) Uani 1 1 d . . . . .
O3 O 0.58395(16) 0.6754(5) 0.56249(15) 0.0288(10) Uani 1 1 d . . . . .
O4 O 0.61176(17) 0.4764(5) 0.53525(18) 0.0330(12) Uani 1 1 d . . . . .
C13 C 0.8094(2) 0.2368(6) 0.64109(19) 0.0235(13) Uani 1 1 d . . . . .
C14 C 0.8285(2) 0.1618(6) 0.6764(2) 0.0280(14) Uani 1 1 d . . . . .
H14 H 0.845306 0.081890 0.676067 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8175(2) 0.2296(7) 0.7119(2) 0.0253(13) Uani 1 1 d . . . . .
H15 H 0.825784 0.205572 0.741442 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8335(2) 0.6437(6) 0.6742(2) 0.0222(12) Uani 1 1 d . . . . .
C17 C 0.8419(2) 0.7557(7) 0.7008(2) 0.0255(13) Uani 1 1 d . . . . .
H17 H 0.868695 0.787953 0.714048 0.031 Uiso 1 1 calc R U . . .
C18 C 0.8024(2) 0.8098(6) 0.7037(2) 0.0214(12) Uani 1 1 d . . . . .
H18 H 0.796637 0.888243 0.719782 0.026 Uiso 1 1 calc R U . . .
C19 C 0.7442(2) 0.7582(6) 0.5696(2) 0.0229(12) Uani 1 1 d . . . . .
C20 C 0.7127(2) 0.8395(7) 0.5478(2) 0.0303(15) Uani 1 1 d . . . . .
H20 H 0.716142 0.920013 0.531656 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6753(2) 0.7781(7) 0.5546(2) 0.0264(14) Uani 1 1 d . . . . .
H21 H 0.647472 0.808785 0.544093 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7050(2) 0.3411(6) 0.54541(18) 0.0206(12) Uani 1 1 d . . . . .
C23 C 0.6803(2) 0.2239(6) 0.5384(2) 0.0240(13) Uani 1 1 d . . . . .
H23 H 0.667360 0.187586 0.511489 0.029 Uiso 1 1 calc R U . . .
C24 C 0.6791(2) 0.1729(6) 0.5795(2) 0.0242(13) Uani 1 1 d . . . . .
H24 H 0.664388 0.093302 0.586498 0.029 Uiso 1 1 calc R U . . .
Cl6 Cl 0.67260(4) 0.53707(14) 0.67958(4) 0.0176(4) Uani 1 1 d . . . . .
Cl7 Cl 0.81112(7) 0.2079(2) 0.58741(5) 0.0408(5) Uani 1 1 d . . . . .
Cl8 Cl 0.86957(5) 0.53231(18) 0.65742(7) 0.0366(5) Uani 1 1 d . . . . .
Cl9 Cl 0.79770(5) 0.78173(19) 0.57248(6) 0.0358(5) Uani 1 1 d . . . . .
Cl10 Cl 0.71848(6) 0.45138(17) 0.50703(5) 0.0332(4) Uani 1 1 d . . . . .
Cu2 Cu 0.75552(3) 0.49612(8) 0.62298(3) 0.0169(3) Uani 1 1 d . . . . .
N9 N 0.78744(17) 0.3419(5) 0.65373(16) 0.0198(10) Uani 1 1 d . . . . .
N10 N 0.79277(17) 0.3371(5) 0.69723(16) 0.0219(11) Uani 1 1 d . . . . .
H10 H 0.781731 0.395601 0.714027 0.026 Uiso 1 1 calc R U . . .
N11 N 0.79196(16) 0.6263(5) 0.66135(16) 0.0189(10) Uani 1 1 d . . . . .
N12 N 0.77387(17) 0.7326(5) 0.67979(17) 0.0211(10) Uani 1 1 d . . . . .
H12A H 0.746383 0.748637 0.676372 0.025 Uiso 1 1 calc R U . . .
N13 N 0.72829(16) 0.6537(5) 0.58896(16) 0.0188(10) Uani 1 1 d . . . . .
N14 N 0.68550(17) 0.6666(5) 0.57877(17) 0.0221(11) Uani 1 1 d . . . . .
H14A H 0.666865 0.609186 0.586993 0.027 Uiso 1 1 calc R U . . .
N15 N 0.71842(17) 0.3622(5) 0.58752(16) 0.0196(10) Uani 1 1 d . . . . .
N16 N 0.70217(16) 0.2548(5) 0.60798(16) 0.0189(10) Uani 1 1 d . . . . .
H16 H 0.706365 0.241242 0.636241 0.023 Uiso 1 1 calc R U . . .
O5 O 0.71256(14) 0.4676(4) 0.67644(14) 0.0202(9) Uani 1 1 d . . . . .
O6 O 0.65517(16) 0.4897(4) 0.71697(16) 0.0251(10) Uani 1 1 d . . . . .
O7 O 0.64334(16) 0.5053(4) 0.64071(15) 0.0237(10) Uani 1 1 d . . . . .
O8 O 0.68019(14) 0.6815(4) 0.68157(14) 0.0223(9) Uani 1 1 d . . . . .
Cl11 Cl 0.57460(5) 0.01956(15) 0.56023(6) 0.0251(4) Uani 1 1 d . . . . .
O9 O 0.59967(19) -0.0359(5) 0.59841(17) 0.0343(12) Uani 1 1 d . . . . .
O10 O 0.53295(18) -0.0399(6) 0.5535(2) 0.0463(15) Uani 1 1 d . . . . .
O11 O 0.57096(16) 0.1659(5) 0.56543(17) 0.0322(11) Uani 1 1 d . . . . .
O12 O 0.59639(18) -0.0056(5) 0.52310(18) 0.0307(12) Uani 1 1 d . . . . .
Cl12 Cl 0.70310(5) 0.03708(14) 0.70453(4) 0.0197(4) Uani 1 1 d . . . . .
O13 O 0.71412(18) -0.0318(5) 0.66692(16) 0.0306(11) Uani 1 1 d . . . . .
O14 O 0.73717(16) 0.0176(5) 0.74082(16) 0.0278(11) Uani 1 1 d . . . . .
O15 O 0.66428(17) -0.0152(5) 0.71691(17) 0.0271(11) Uani 1 1 d . . . . .
O16 O 0.69836(15) 0.1826(4) 0.69544(14) 0.0246(10) 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
C1 N2 1.352(9) . ?
C1 C2 1.370(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(9) . ?
C2 H2 0.9500 . ?
C3 N1 1.339(8) . ?
C3 Cl2 1.711(7) . ?
C4 N3 1.343(8) . ?
C4 C5 1.391(9) . ?
C4 Cl3 1.705(7) . ?
C5 C6 1.367(10) . ?
C5 H5 0.9500 . ?
C6 N4 1.336(9) . ?
C6 H6 0.9500 . ?
C7 N5 1.331(8) . ?
C7 C8 1.385(9) . ?
C7 Cl4 1.709(7) . ?
C8 C9 1.373(10) . ?
C8 H8 0.9500 . ?
C9 N6 1.329(8) . ?
C9 H9 0.9500 . ?
C10 N7 1.341(8) . ?
C10 C11 1.388(9) . ?
C10 Cl5 1.699(7) . ?
C11 C12 1.366(9) . ?
C11 H11 0.9500 . ?
C12 N8 1.335(8) . ?
C12 H12 0.9500 . ?
Cl1 O4 1.428(5) . ?
Cl1 O3 1.440(5) . ?
Cl1 O2 1.442(5) . ?
Cl1 O1 1.461(5) . ?
Cu1 N5 1.985(5) . ?
Cu1 N1 2.007(5) . ?
Cu1 N3 2.013(5) . ?
Cu1 N7 2.020(5) . ?
Cu1 O1 2.285(5) . ?
N1 N2 1.353(7) . ?
N2 H2A 0.8800 . ?
N3 N4 1.340(7) . ?
N4 H4 0.8800 . ?
N5 N6 1.366(7) . ?
N6 H6A 0.8800 . ?
N7 N8 1.373(7) . ?
N8 H8A 0.8800 . ?
C13 N9 1.334(8) . ?
C13 C14 1.392(9) . ?
C13 Cl7 1.699(6) . ?
C14 C15 1.370(9) . ?
C14 H14 0.9500 . ?
C15 N10 1.358(8) . ?
C15 H15 0.9500 . ?
C16 N11 1.338(8) . ?
C16 C17 1.380(9) . ?
C16 Cl8 1.715(7) . ?
C17 C18 1.376(9) . ?
C17 H17 0.9500 . ?
C18 N12 1.330(8) . ?
C18 H18 0.9500 . ?
C19 N13 1.323(8) . ?
C19 C20 1.385(9) . ?
C19 Cl9 1.707(6) . ?
C20 C21 1.373(10) . ?
C20 H20 0.9500 . ?
C21 N14 1.343(8) . ?
C21 H21 0.9500 . ?
C22 N15 1.336(7) . ?
C22 C23 1.394(8) . ?
C22 Cl10 1.707(6) . ?
C23 C24 1.377(9) . ?
C23 H23 0.9500 . ?
C24 N16 1.339(8) . ?
C24 H24 0.9500 . ?
Cl6 O6 1.430(5) . ?
Cl6 O8 1.438(4) . ?
Cl6 O7 1.456(5) . ?
Cl6 O5 1.457(5) . ?
Cu2 N9 1.994(5) . ?
Cu2 N15 1.996(5) . ?
Cu2 N13 2.004(5) . ?
Cu2 N11 2.006(5) . ?
Cu2 O5 2.303(4) . ?
N9 N10 1.339(7) . ?
N10 H10 0.8800 . ?
N11 N12 1.355(7) . ?
N12 H12A 0.8800 . ?
N13 N14 1.361(7) . ?
N14 H14A 0.8800 . ?
N15 N16 1.368(7) . ?
N16 H16 0.8800 . ?
Cl11 O10 1.437(6) . ?
Cl11 O12 1.443(6) . ?
Cl11 O9 1.444(5) . ?
Cl11 O11 1.452(5) . ?
Cl12 O13 1.433(5) . ?
Cl12 O15 1.436(5) . ?
Cl12 O16 1.460(4) . ?
Cl12 O14 1.467(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
N2 C1 C2 108.1(6) . . ?
N2 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
C1 C2 C3 104.3(6) . . ?
C1 C2 H2 127.8 . . ?
C3 C2 H2 127.8 . . ?
N1 C3 C2 111.5(6) . . ?
N1 C3 Cl2 120.3(5) . . ?
C2 C3 Cl2 128.1(5) . . ?
N3 C4 C5 111.4(6) . . ?
N3 C4 Cl3 120.6(5) . . ?
C5 C4 Cl3 128.0(5) . . ?
C6 C5 C4 104.0(6) . . ?
C6 C5 H5 128.0 . . ?
C4 C5 H5 128.0 . . ?
N4 C6 C5 108.4(6) . . ?
N4 C6 H6 125.8 . . ?
C5 C6 H6 125.8 . . ?
N5 C7 C8 111.8(6) . . ?
N5 C7 Cl4 120.1(5) . . ?
C8 C7 Cl4 128.1(5) . . ?
C9 C8 C7 104.6(6) . . ?
C9 C8 H8 127.7 . . ?
C7 C8 H8 127.7 . . ?
N6 C9 C8 107.9(6) . . ?
N6 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
N7 C10 C11 111.4(6) . . ?
N7 C10 Cl5 122.2(5) . . ?
C11 C10 Cl5 126.3(5) . . ?
C12 C11 C10 105.1(6) . . ?
C12 C11 H11 127.5 . . ?
C10 C11 H11 127.5 . . ?
N8 C12 C11 108.0(6) . . ?
N8 C12 H12 126.0 . . ?
C11 C12 H12 126.0 . . ?
O4 Cl1 O3 109.9(3) . . ?
O4 Cl1 O2 110.8(3) . . ?
O3 Cl1 O2 109.6(3) . . ?
O4 Cl1 O1 109.8(3) . . ?
O3 Cl1 O1 108.9(3) . . ?
O2 Cl1 O1 107.8(3) . . ?
N5 Cu1 N1 174.7(2) . . ?
N5 Cu1 N3 88.3(2) . . ?
N1 Cu1 N3 90.4(2) . . ?
N5 Cu1 N7 90.4(2) . . ?
N1 Cu1 N7 91.0(2) . . ?
N3 Cu1 N7 178.6(2) . . ?
N5 Cu1 O1 83.90(19) . . ?
N1 Cu1 O1 101.2(2) . . ?
N3 Cu1 O1 88.60(19) . . ?
N7 Cu1 O1 91.08(19) . . ?
C3 N1 N2 105.1(5) . . ?
C3 N1 Cu1 133.8(4) . . ?
N2 N1 Cu1 120.0(4) . . ?
C1 N2 N1 111.0(6) . . ?
C1 N2 H2A 124.5 . . ?
N1 N2 H2A 124.5 . . ?
N4 N3 C4 104.8(5) . . ?
N4 N3 Cu1 120.4(4) . . ?
C4 N3 Cu1 134.7(5) . . ?
C6 N4 N3 111.5(5) . . ?
C6 N4 H4 124.3 . . ?
N3 N4 H4 124.3 . . ?
C7 N5 N6 104.4(5) . . ?
C7 N5 Cu1 135.0(4) . . ?
N6 N5 Cu1 120.2(4) . . ?
C9 N6 N5 111.3(5) . . ?
C9 N6 H6A 124.3 . . ?
N5 N6 H6A 124.3 . . ?
C10 N7 N8 104.2(5) . . ?
C10 N7 Cu1 136.0(4) . . ?
N8 N7 Cu1 118.9(4) . . ?
C12 N8 N7 111.2(5) . . ?
C12 N8 H8A 124.4 . . ?
N7 N8 H8A 124.4 . . ?
Cl1 O1 Cu1 133.8(3) . . ?
N9 C13 C14 111.6(5) . . ?
N9 C13 Cl7 120.3(5) . . ?
C14 C13 Cl7 128.1(5) . . ?
C15 C14 C13 104.2(6) . . ?
C15 C14 H14 127.9 . . ?
C13 C14 H14 127.9 . . ?
N10 C15 C14 107.9(5) . . ?
N10 C15 H15 126.1 . . ?
C14 C15 H15 126.1 . . ?
N11 C16 C17 112.6(6) . . ?
N11 C16 Cl8 120.1(5) . . ?
C17 C16 Cl8 127.3(5) . . ?
C18 C17 C16 104.0(6) . . ?
C18 C17 H17 128.0 . . ?
C16 C17 H17 128.0 . . ?
N12 C18 C17 107.7(5) . . ?
N12 C18 H18 126.2 . . ?
C17 C18 H18 126.2 . . ?
N13 C19 C20 112.0(6) . . ?
N13 C19 Cl9 121.3(5) . . ?
C20 C19 Cl9 126.7(5) . . ?
C21 C20 C19 104.8(6) . . ?
C21 C20 H20 127.6 . . ?
C19 C20 H20 127.6 . . ?
N14 C21 C20 107.2(6) . . ?
N14 C21 H21 126.4 . . ?
C20 C21 H21 126.4 . . ?
N15 C22 C23 112.4(5) . . ?
N15 C22 Cl10 120.5(5) . . ?
C23 C22 Cl10 127.1(5) . . ?
C24 C23 C22 103.9(5) . . ?
C24 C23 H23 128.0 . . ?
C22 C23 H23 128.0 . . ?
N16 C24 C23 108.2(6) . . ?
N16 C24 H24 125.9 . . ?
C23 C24 H24 125.9 . . ?
O6 Cl6 O8 111.5(3) . . ?
O6 Cl6 O7 109.2(3) . . ?
O8 Cl6 O7 109.4(3) . . ?
O6 Cl6 O5 109.8(3) . . ?
O8 Cl6 O5 108.8(3) . . ?
O7 Cl6 O5 108.1(3) . . ?
N9 Cu2 N15 89.4(2) . . ?
N9 Cu2 N13 174.4(2) . . ?
N15 Cu2 N13 92.1(2) . . ?
N9 Cu2 N11 89.0(2) . . ?
N15 Cu2 N11 177.1(2) . . ?
N13 Cu2 N11 89.7(2) . . ?
N9 Cu2 O5 82.83(18) . . ?
N15 Cu2 O5 87.36(18) . . ?
N13 Cu2 O5 102.60(18) . . ?
N11 Cu2 O5 90.02(18) . . ?
C13 N9 N10 105.6(5) . . ?
C13 N9 Cu2 134.4(4) . . ?
N10 N9 Cu2 119.8(4) . . ?
N9 N10 C15 110.8(5) . . ?
N9 N10 H10 124.6 . . ?
C15 N10 H10 124.6 . . ?
C16 N11 N12 103.5(5) . . ?
C16 N11 Cu2 136.6(4) . . ?
N12 N11 Cu2 119.8(4) . . ?
C18 N12 N11 112.2(5) . . ?
C18 N12 H12A 123.9 . . ?
N11 N12 H12A 123.9 . . ?
C19 N13 N14 104.6(5) . . ?
C19 N13 Cu2 132.4(4) . . ?
N14 N13 Cu2 122.8(4) . . ?
C21 N14 N13 111.4(5) . . ?
C21 N14 H14A 124.3 . . ?
N13 N14 H14A 124.3 . . ?
C22 N15 N16 104.1(5) . . ?
C22 N15 Cu2 136.9(4) . . ?
N16 N15 Cu2 118.9(4) . . ?
C24 N16 N15 111.4(5) . . ?
C24 N16 H16 124.3 . . ?
N15 N16 H16 124.3 . . ?
Cl6 O5 Cu2 126.7(3) . . ?
O10 Cl11 O12 110.2(4) . . ?
O10 Cl11 O9 111.3(4) . . ?
O12 Cl11 O9 108.7(3) . . ?
O10 Cl11 O11 109.5(3) . . ?
O12 Cl11 O11 108.2(3) . . ?
O9 Cl11 O11 109.0(3) . . ?
O13 Cl12 O15 111.2(3) . . ?
O13 Cl12 O16 109.5(3) . . ?
O15 Cl12 O16 109.4(3) . . ?
O13 Cl12 O14 109.2(3) . . ?
O15 Cl12 O14 108.7(3) . . ?
O16 Cl12 O14 108.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 0.6(8) . . . . ?
C1 C2 C3 N1 0.4(8) . . . . ?
C1 C2 C3 Cl2 -177.9(6) . . . . ?
N3 C4 C5 C6 0.6(8) . . . . ?
Cl3 C4 C5 C6 -179.7(6) . . . . ?
C4 C5 C6 N4 -0.4(8) . . . . ?
N5 C7 C8 C9 0.1(8) . . . . ?
Cl4 C7 C8 C9 -179.1(5) . . . . ?
C7 C8 C9 N6 0.0(7) . . . . ?
N7 C10 C11 C12 -1.9(8) . . . . ?
Cl5 C10 C11 C12 176.2(5) . . . . ?
C10 C11 C12 N8 2.7(7) . . . . ?
C2 C3 N1 N2 -1.2(8) . . . . ?
Cl2 C3 N1 N2 177.3(5) . . . . ?
C2 C3 N1 Cu1 -168.7(5) . . . . ?
Cl2 C3 N1 Cu1 9.8(9) . . . . ?
C2 C1 N2 N1 -1.4(8) . . . . ?
C3 N1 N2 C1 1.6(7) . . . . ?
Cu1 N1 N2 C1 171.2(5) . . . . ?
C5 C4 N3 N4 -0.5(7) . . . . ?
Cl3 C4 N3 N4 179.8(5) . . . . ?
C5 C4 N3 Cu1 -177.0(5) . . . . ?
Cl3 C4 N3 Cu1 3.3(9) . . . . ?
C5 C6 N4 N3 0.1(8) . . . . ?
C4 N3 N4 C6 0.2(7) . . . . ?
Cu1 N3 N4 C6 177.3(4) . . . . ?
C8 C7 N5 N6 -0.1(7) . . . . ?
Cl4 C7 N5 N6 179.1(4) . . . . ?
C8 C7 N5 Cu1 -172.6(5) . . . . ?
Cl4 C7 N5 Cu1 6.7(9) . . . . ?
C8 C9 N6 N5 -0.1(8) . . . . ?
C7 N5 N6 C9 0.1(7) . . . . ?
Cu1 N5 N6 C9 173.9(4) . . . . ?
C11 C10 N7 N8 0.3(7) . . . . ?
Cl5 C10 N7 N8 -177.9(4) . . . . ?
C11 C10 N7 Cu1 -167.9(5) . . . . ?
Cl5 C10 N7 Cu1 13.9(9) . . . . ?
C11 C12 N8 N7 -2.7(7) . . . . ?
C10 N7 N8 C12 1.5(7) . . . . ?
Cu1 N7 N8 C12 172.1(4) . . . . ?
O4 Cl1 O1 Cu1 172.1(4) . . . . ?
O3 Cl1 O1 Cu1 51.7(5) . . . . ?
O2 Cl1 O1 Cu1 -67.1(4) . . . . ?
N9 C13 C14 C15 -1.2(8) . . . . ?
Cl7 C13 C14 C15 179.3(6) . . . . ?
C13 C14 C15 N10 0.9(8) . . . . ?
N11 C16 C17 C18 -0.7(7) . . . . ?
Cl8 C16 C17 C18 179.5(5) . . . . ?
C16 C17 C18 N12 -0.3(7) . . . . ?
N13 C19 C20 C21 -0.3(8) . . . . ?
Cl9 C19 C20 C21 179.2(5) . . . . ?
C19 C20 C21 N14 -0.6(8) . . . . ?
N15 C22 C23 C24 0.2(8) . . . . ?
Cl10 C22 C23 C24 -179.9(5) . . . . ?
C22 C23 C24 N16 -0.9(8) . . . . ?
C14 C13 N9 N10 1.1(7) . . . . ?
Cl7 C13 N9 N10 -179.4(5) . . . . ?
C14 C13 N9 Cu2 175.7(5) . . . . ?
Cl7 C13 N9 Cu2 -4.8(9) . . . . ?
C13 N9 N10 C15 -0.5(7) . . . . ?
Cu2 N9 N10 C15 -176.1(4) . . . . ?
C14 C15 N10 N9 -0.3(8) . . . . ?
C17 C16 N11 N12 1.4(7) . . . . ?
Cl8 C16 N11 N12 -178.8(4) . . . . ?
C17 C16 N11 Cu2 178.2(5) . . . . ?
Cl8 C16 N11 Cu2 -2.0(9) . . . . ?
C17 C18 N12 N11 1.2(7) . . . . ?
C16 N11 N12 C18 -1.6(7) . . . . ?
Cu2 N11 N12 C18 -179.1(4) . . . . ?
C20 C19 N13 N14 1.1(7) . . . . ?
Cl9 C19 N13 N14 -178.5(5) . . . . ?
C20 C19 N13 Cu2 176.9(5) . . . . ?
Cl9 C19 N13 Cu2 -2.7(8) . . . . ?
C20 C21 N14 N13 1.3(8) . . . . ?
C19 N13 N14 C21 -1.4(7) . . . . ?
Cu2 N13 N14 C21 -177.8(4) . . . . ?
C23 C22 N15 N16 0.6(7) . . . . ?
Cl10 C22 N15 N16 -179.4(4) . . . . ?
C23 C22 N15 Cu2 176.8(5) . . . . ?
Cl10 C22 N15 Cu2 -3.2(9) . . . . ?
C23 C24 N16 N15 1.4(8) . . . . ?
C22 N15 N16 C24 -1.2(7) . . . . ?
Cu2 N15 N16 C24 -178.2(4) . . . . ?
O6 Cl6 O5 Cu2 179.0(3) . . . . ?
O8 Cl6 O5 Cu2 -58.8(4) . . . . ?
O7 Cl6 O5 Cu2 59.9(4) . . . . ?

_refine_diff_density_max         2.205
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.209


# start Validation Reply Form
_vrf_PLAT084_2a                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: The high wR2 value is attributed to the poor quality of the crystal.
;
_vrf_PLAT430_2a                  
;
PROBLEM: Short Inter D...A Contact  O2       ..O2       .       2.69 Ang.  
RESPONSE: This structure shows the short O...O distances which is
thought to result from molecule packing force.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2388294'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cl2 Cu I2 N6 O8'
_chemical_formula_weight         732.51

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.9186(3)
_cell_length_b                   11.1291(3)
_cell_length_c                   13.1374(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.5270(10)
_cell_angle_gamma                90
_cell_volume                     1026.69(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2333
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.97

_exptl_crystal_description       block
_exptl_crystal_colour            'light green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    4.382
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            11452
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1804
_reflns_number_gt                1423
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0469P)²+0.4163P] 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         1804
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
I1 I 1.00398(6) 0.68206(4) 0.58724(4) 0.03632(19) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0292(3) Uani 1 2 d S . P . .
Cl1 Cl 0.6788(2) 0.20749(15) 0.59431(14) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.6605(7) 0.2350(5) 0.6950(4) 0.0477(14) Uani 1 1 d . . . . .
N1 N 0.6458(7) 0.5656(4) 0.4182(4) 0.0257(12) Uani 1 1 d . . . . .
N3 N 0.3276(8) 0.4545(5) 0.3396(5) 0.0328(13) Uani 1 1 d . . . . .
H3 H 0.226261 0.413538 0.323567 0.039 Uiso 1 1 calc R U . . .
N2 N 0.5437(7) 0.5417(5) 0.3013(4) 0.0260(12) Uani 1 1 d . . . . .
O2 O 0.8441(8) 0.1380(5) 0.6215(5) 0.0610(16) Uani 1 1 d . . . . .
O1 O 0.6875(10) 0.3145(5) 0.5394(6) 0.072(2) Uani 1 1 d . . . . .
C4 C 0.3659(9) 0.4850(6) 0.2629(6) 0.0280(15) Uani 1 1 d . . . . .
C1 C 0.7945(9) 0.6255(6) 0.4291(6) 0.0287(15) Uani 1 1 d . . . . .
C3 C 0.6351(9) 0.5892(6) 0.2458(6) 0.0305(16) Uani 1 1 d . . . . .
H3A H 0.594981 0.584876 0.167242 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7934(10) 0.6435(6) 0.3231(6) 0.0327(16) Uani 1 1 d . . . . .
H2 H 0.883329 0.684490 0.309500 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2519(9) 0.4724(6) 0.1362(5) 0.0320(16) Uani 1 1 d . . . . .
H5A H 0.128422 0.440790 0.118104 0.048 Uiso 1 1 calc R U . . .
H5B H 0.315735 0.418719 0.108112 0.048 Uiso 1 1 calc R U . . .
H5C H 0.237981 0.549691 0.100672 0.048 Uiso 1 1 calc R U . . .
O4 O 0.5182(10) 0.1415(7) 0.5210(6) 0.093(3) 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
I1 C1 2.068(7) . ?
Cu1 N3 1.976(5) 3_666 ?
Cu1 N3 1.976(5) . ?
Cu1 N1 2.042(5) . ?
Cu1 N1 2.042(5) 3_666 ?
Cu1 O1 2.454(5) . ?
Cl1 O4 1.398(6) . ?
Cl1 O1 1.410(5) . ?
Cl1 O2 1.417(5) . ?
Cl1 O3 1.429(5) . ?
N1 C1 1.302(8) . ?
N1 N2 1.391(7) . ?
N3 C4 1.227(8) . ?
N3 H3 0.8600 . ?
N2 C3 1.350(7) . ?
N2 C4 1.406(8) . ?
C4 C5 1.488(9) . ?
C1 C2 1.402(9) . ?
C3 C2 1.339(9) . ?
C3 H3A 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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 3_666 . ?
N3 Cu1 N1 100.9(2) 3_666 . ?
N3 Cu1 N1 79.1(2) . . ?
N3 Cu1 N1 79.1(2) 3_666 3_666 ?
N3 Cu1 N1 100.9(2) . 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
N3 Cu1 O1 86.4(2) 3_666 . ?
N3 Cu1 O1 93.6(2) . . ?
N1 Cu1 O1 88.71(18) . . ?
N1 Cu1 O1 91.29(19) 3_666 . ?
O4 Cl1 O1 109.6(5) . . ?
O4 Cl1 O2 109.1(4) . . ?
O1 Cl1 O2 109.4(4) . . ?
O4 Cl1 O3 107.5(4) . . ?
O1 Cl1 O3 110.0(3) . . ?
O2 Cl1 O3 111.2(3) . . ?
C1 N1 N2 104.7(5) . . ?
C1 N1 Cu1 145.9(5) . . ?
N2 N1 Cu1 109.3(4) . . ?
C4 N3 Cu1 119.6(5) . . ?
C4 N3 H3 120.2 . . ?
Cu1 N3 H3 120.2 . . ?
C3 N2 N1 109.7(5) . . ?
C3 N2 C4 132.8(6) . . ?
N1 N2 C4 117.2(5) . . ?
Cl1 O1 Cu1 130.6(3) . . ?
N3 C4 N2 114.6(6) . . ?
N3 C4 C5 129.8(6) . . ?
N2 C4 C5 115.6(5) . . ?
N1 C1 C2 111.9(6) . . ?
N1 C1 I1 122.1(5) . . ?
C2 C1 I1 126.0(5) . . ?
C2 C3 N2 108.3(6) . . ?
C2 C3 H3A 125.8 . . ?
N2 C3 H3A 125.8 . . ?
C3 C2 C1 105.3(6) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -0.4(7) . . . . ?
Cu1 N1 N2 C3 177.4(4) . . . . ?
C1 N1 N2 C4 -175.2(5) . . . . ?
Cu1 N1 N2 C4 2.6(6) . . . . ?
O4 Cl1 O1 Cu1 74.6(6) . . . . ?
O2 Cl1 O1 Cu1 -165.9(5) . . . . ?
O3 Cl1 O1 Cu1 -43.5(6) . . . . ?
Cu1 N3 C4 N2 5.7(8) . . . . ?
Cu1 N3 C4 C5 -173.5(5) . . . . ?
C3 N2 C4 N3 -178.8(6) . . . . ?
N1 N2 C4 N3 -5.4(8) . . . . ?
C3 N2 C4 C5 0.5(10) . . . . ?
N1 N2 C4 C5 173.9(5) . . . . ?
N2 N1 C1 C2 0.7(7) . . . . ?
Cu1 N1 C1 C2 -175.5(6) . . . . ?
N2 N1 C1 I1 -178.3(4) . . . . ?
Cu1 N1 C1 I1 5.4(11) . . . . ?
N1 N2 C3 C2 -0.2(7) . . . . ?
C4 N2 C3 C2 173.6(6) . . . . ?
N2 C3 C2 C1 0.6(7) . . . . ?
N1 C1 C2 C3 -0.9(8) . . . . ?
I1 C1 C2 C3 178.2(5) . . . . ?

_refine_diff_density_max         1.262
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.157

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2388295'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_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                   7.8033(5)
_cell_length_b                   9.4838(6)
_cell_length_c                   12.8328(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.447(4)
_cell_angle_gamma                90
_cell_volume                     906.00(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8230
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.65

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.559
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            29538
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.717
_diffrn_reflns_theta_max         28.743
_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             2352
_reflns_number_gt                1958
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.1200P)²+0.0600P] 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         2352
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.000000 0.000000 1.000000 0.02073(18) Uani 1 2 d S . P . .
Cl1 Cl 0.19343(8) 0.01128(5) 1.29352(5) 0.02284(19) Uani 1 1 d . . . . .
O4 O 0.1198(3) 0.1483(2) 1.30112(16) 0.0482(6) Uani 1 1 d . . . . .
O3 O 0.3597(3) -0.00480(16) 1.37996(18) 0.0352(5) Uani 1 1 d . . . . .
O2 O 0.0682(3) -0.0941(2) 1.30312(15) 0.0463(6) Uani 1 1 d . . . . .
O1 O 0.2270(3) -0.00253(16) 1.18950(16) 0.0326(5) Uani 1 1 d . . . . .
N3 N 0.0719(3) 0.19653(19) 0.98138(16) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.018092 0.269098 1.000790 0.032 Uiso 1 1 calc R U . . .
N1 N 0.1947(2) -0.03597(19) 0.93178(13) 0.0193(4) Uani 1 1 d . . . . .
N2 N 0.2699(2) 0.08783(18) 0.91202(13) 0.0192(4) Uani 1 1 d . . . . .
C3 C 0.4146(3) -0.0800(3) 0.85712(15) 0.0209(5) Uani 1 1 d . . . . .
H3A H 0.495874 -0.130743 0.828904 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4042(3) 0.0628(3) 0.86662(16) 0.0207(5) Uani 1 1 d . . . . .
H4 H 0.476343 0.131384 0.845716 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2802(3) -0.1371(2) 0.89769(15) 0.0199(4) Uani 1 1 d . . . . .
C5 C 0.1999(3) 0.2125(2) 0.93987(16) 0.0214(4) Uani 1 1 d . . . . .
C6 C 0.2807(3) 0.3473(2) 0.92094(19) 0.0268(5) Uani 1 1 d . . . . .
H6A H 0.195389 0.424225 0.917734 0.040 Uiso 1 1 calc R U . . .
H6B H 0.309320 0.342471 0.851712 0.040 Uiso 1 1 calc R U . . .
H6C H 0.390852 0.364593 0.980802 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2346(3) -0.2893(2) 0.90386(18) 0.0256(5) Uani 1 1 d . . . . .
H1A H 0.260742 -0.317303 0.980560 0.038 Uiso 1 1 calc R U . . .
H1B H 0.306410 -0.346612 0.868966 0.038 Uiso 1 1 calc R U . . .
H1C H 0.106632 -0.303911 0.866084 0.038 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 1.9814(18) . ?
Cu1 N3 1.9814(18) 3_557 ?
Cu1 N1 1.9971(17) 3_557 ?
Cu1 N1 1.9972(17) . ?
Cu1 O1 2.543(2) . ?
Cl1 O2 1.4288(19) . ?
Cl1 O4 1.436(2) . ?
Cl1 O3 1.440(2) . ?
Cl1 O1 1.4412(19) . ?
N3 C5 1.274(3) . ?
N3 H3 0.8800 . ?
N1 C2 1.315(3) . ?
N1 N2 1.370(2) . ?
N2 C4 1.364(3) . ?
N2 C5 1.393(2) . ?
C3 C4 1.365(4) . ?
C3 C2 1.411(3) . ?
C3 H3A 0.9500 . ?
C4 H4 0.9500 . ?
C2 C1 1.495(3) . ?
C5 C6 1.477(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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(3) . 3_557 ?
N3 Cu1 N1 99.91(7) . 3_557 ?
N3 Cu1 N1 80.09(7) 3_557 3_557 ?
N3 Cu1 N1 80.08(7) . . ?
N3 Cu1 N1 99.92(7) 3_557 . ?
N1 Cu1 N1 180.00(7) 3_557 . ?
N3 Cu1 O1 89.03(7) . . ?
N3 Cu1 O1 90.97(7) 3_557 . ?
N1 Cu1 O1 89.18(7) 3_557 . ?
N1 Cu1 O1 90.82(7) . . ?
O2 Cl1 O4 109.22(14) . . ?
O2 Cl1 O3 109.94(12) . . ?
O4 Cl1 O3 109.28(12) . . ?
O2 Cl1 O1 109.58(11) . . ?
O4 Cl1 O1 109.43(11) . . ?
O3 Cl1 O1 109.38(13) . . ?
Cl1 O1 Cu1 128.10(12) . . ?
C5 N3 Cu1 116.62(15) . . ?
C5 N3 H3 121.7 . . ?
Cu1 N3 H3 121.7 . . ?
C2 N1 N2 105.97(16) . . ?
C2 N1 Cu1 142.98(15) . . ?
N2 N1 Cu1 111.05(13) . . ?
C4 N2 N1 110.90(17) . . ?
C4 N2 C5 131.90(18) . . ?
N1 N2 C5 117.20(16) . . ?
C4 C3 C2 106.07(18) . . ?
C4 C3 H3A 127.0 . . ?
C2 C3 H3A 127.0 . . ?
N2 C4 C3 106.55(19) . . ?
N2 C4 H4 126.7 . . ?
C3 C4 H4 126.7 . . ?
N1 C2 C3 110.50(19) . . ?
N1 C2 C1 122.28(18) . . ?
C3 C2 C1 127.22(19) . . ?
N3 C5 N2 115.03(18) . . ?
N3 C5 C6 126.75(19) . . ?
N2 C5 C6 118.21(18) . . ?
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 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2388293'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Br2 Cl2 Cu N6 O8'
_chemical_formula_weight         638.51

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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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                   7.8326(4)
_cell_length_b                   10.9412(7)
_cell_length_c                   11.5905(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.897(2)
_cell_angle_gamma                90
_cell_volume                     983.86(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4765
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.61

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    5.496
_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  0.644
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            13025
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.1193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         28.952
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2559
_reflns_number_gt                2072
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+0.9132P] 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         2559
_refine_ls_number_parameters     134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_restrained_S_all      1.244
_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
Br1 Br 0.08671(4) 0.32339(4) 0.57776(3) 0.02784(13) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.02014(16) Uani 1 2 d S . P . .
Cl1 Cl 0.58289(10) 0.20556(9) 0.39757(7) 0.0223(2) Uani 1 1 d D . . . .
O3 O 0.4651(3) 0.2372(3) 0.29780(18) 0.0338(7) Uani 1 1 d D . . . .
O1 O 0.6558(3) 0.3137(3) 0.4551(3) 0.0380(7) Uani 1 1 d . . . . .
N3 N 0.5171(4) 0.5466(3) 0.3375(3) 0.0230(7) Uani 1 1 d . . . . .
H3 H 0.604070 0.587619 0.320616 0.028 Uiso 1 1 calc R U . . .
N2 N 0.2570(3) 0.4603(3) 0.3020(3) 0.0205(6) Uani 1 1 d . . . . .
N1 N 0.2724(3) 0.4375(3) 0.4191(2) 0.0190(6) Uani 1 1 d . . . . .
O4 O 0.7193(3) 0.1324(3) 0.3635(3) 0.0452(8) Uani 1 1 d . . . . .
O2 O 0.4934(4) 0.1383(3) 0.4749(3) 0.0522(9) Uani 1 1 d . . . . .
C1 C 0.1301(4) 0.3766(4) 0.4321(3) 0.0231(8) Uani 1 1 d . . . . .
C4 C 0.3989(4) 0.5153(4) 0.2598(3) 0.0214(8) Uani 1 1 d . . . . .
C3 C 0.1080(4) 0.4127(4) 0.2443(3) 0.0237(8) Uani 1 1 d . . . . .
H3A H 0.071655 0.416177 0.164503 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0229(4) 0.3593(4) 0.3258(3) 0.0266(8) Uani 1 1 d . . . . .
H2 H -0.083290 0.319864 0.313749 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3885(5) 0.5256(4) 0.1311(3) 0.0272(9) Uani 1 1 d . . . . .
H5A H 0.490095 0.565440 0.111965 0.041 Uiso 1 1 calc R U . . .
H5B H 0.288624 0.572558 0.101123 0.041 Uiso 1 1 calc R U . . .
H5C H 0.379934 0.445423 0.097147 0.041 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
Br1 C1 1.861(4) . ?
Cu1 N3 1.974(3) 3_666 ?
Cu1 N3 1.974(3) . ?
Cu1 N1 2.016(3) . ?
Cu1 N1 2.016(3) 3_666 ?
Cu1 O1 2.468(3) . ?
Cl1 O2 1.417(3) . ?
Cl1 O3 1.4194(16) . ?
Cl1 O4 1.433(3) . ?
Cl1 O1 1.437(3) . ?
N3 C4 1.248(4) . ?
N3 H3 0.8600 . ?
N2 C3 1.366(4) . ?
N2 N1 1.369(4) . ?
N2 C4 1.409(4) . ?
N1 C1 1.325(4) . ?
C1 C2 1.405(5) . ?
C4 C5 1.486(5) . ?
C3 C2 1.361(5) . ?
C3 H3A 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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(5) 3_666 . ?
N3 Cu1 N1 100.63(11) 3_666 . ?
N3 Cu1 N1 79.37(11) . . ?
N3 Cu1 N1 79.37(11) 3_666 3_666 ?
N3 Cu1 N1 100.63(11) . 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
N3 Cu1 O1 95.04(12) 3_666 . ?
N3 Cu1 O1 84.96(12) . . ?
N1 Cu1 O1 93.05(11) . . ?
N1 Cu1 O1 86.95(11) 3_666 . ?
O2 Cl1 O3 108.62(18) . . ?
O2 Cl1 O4 109.7(2) . . ?
O3 Cl1 O4 109.71(18) . . ?
O2 Cl1 O1 109.4(2) . . ?
O3 Cl1 O1 110.47(19) . . ?
O4 Cl1 O1 108.89(18) . . ?
Cl1 O1 Cu1 126.96(15) . . ?
C4 N3 Cu1 118.5(2) . . ?
C4 N3 H3 120.8 . . ?
Cu1 N3 H3 120.8 . . ?
C3 N2 N1 111.7(3) . . ?
C3 N2 C4 130.9(3) . . ?
N1 N2 C4 117.1(3) . . ?
C1 N1 N2 104.1(3) . . ?
C1 N1 Cu1 145.3(3) . . ?
N2 N1 Cu1 110.56(19) . . ?
N1 C1 C2 112.3(3) . . ?
N1 C1 Br1 121.4(3) . . ?
C2 C1 Br1 126.3(3) . . ?
N3 C4 N2 114.1(3) . . ?
N3 C4 C5 129.5(3) . . ?
N2 C4 C5 116.3(3) . . ?
C2 C3 N2 106.9(3) . . ?
C2 C3 H3A 126.5 . . ?
N2 C3 H3A 126.5 . . ?
C3 C2 C1 105.1(3) . . ?
C3 C2 H2 127.5 . . ?
C1 C2 H2 127.5 . . ?
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 . . ?

_refine_diff_density_max         0.811
_refine_diff_density_min         -1.244
_refine_diff_density_rms         0.157


# start Validation Reply Form
_vrf_PLAT431_1b                  
;
PROBLEM: Short Inter HL..A Contact  Br1      ..O3       .       2.92 Ang.  
RESPONSE: The bond lengths of C-Br and Cl-O were checked and found to be within 
reasonable ranges. We even slightly restricted the Cl-O2 bond length, but the 
warning still appears. We believe this is simply due to the tight packing of 
the molecules.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1e''
_database_code_depnum_ccdc_archive 'CCDC 2388298'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 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 H30 B2 Cu F8 N6'
_chemical_formula_weight         567.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   31.3023(4)
_cell_length_b                   7.10072(7)
_cell_length_c                   11.71542(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2603.97(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_max      74.4100
_cell_measurement_theta_min      2.7990

_exptl_crystal_description       needle
_exptl_crystal_colour            'bluish violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             1164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.876
_shelx_estimated_absorpt_T_min   0.683
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91336
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17905
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         74.841
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             4862
_reflns_number_gt                4551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.833
_reflns_Friedel_fraction_full    0.909

_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_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'

_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)+(0.0428P)²+0.6947P] 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     SHELXL
_refine_ls_extinction_coef       0.00038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4862
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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
F8 F 0.61321(8) 0.9884(4) 0.3561(2) 0.0525(7) Uani 1 1 d . . . . .
B2 B 0.57789(13) 1.0775(6) 0.3097(4) 0.0336(9) Uani 1 1 d . . . . .
F7 F 0.56330(10) 0.9807(3) 0.2172(3) 0.0656(9) Uani 1 1 d . . . . .
F5 F 0.58890(9) 1.2589(3) 0.2744(2) 0.0527(7) Uani 1 1 d . . . . .
F6 F 0.54601(9) 1.0937(4) 0.3905(3) 0.0655(8) Uani 1 1 d . . . . .
B1 B 0.66965(14) 0.3713(6) 0.6866(4) 0.0330(9) Uani 1 1 d . . . . .
C12 C 0.74976(11) 0.6856(5) 0.4237(3) 0.0283(7) Uani 1 1 d . . . . .
H12 H 0.7707 0.6162 0.3829 0.034 Uiso 1 1 calc R U . . .
C11 C 0.75703(9) 0.8381(4) 0.4924(4) 0.0272(6) Uani 1 1 d . . . . .
C10 C 0.71601(11) 0.8892(5) 0.5331(3) 0.0285(7) Uani 1 1 d . . . . .
H10 H 0.7107 0.9916 0.5833 0.034 Uiso 1 1 calc R U . . .
C17 C 0.68169(11) 0.5122(5) 0.3714(3) 0.0289(8) Uani 1 1 d . . . . .
C18 C 0.70422(12) 0.3663(6) 0.3033(4) 0.0420(10) Uani 1 1 d . . . . .
H18A H 0.6832 0.2877 0.2637 0.063 Uiso 1 1 calc R U . . .
H18B H 0.7215 0.2876 0.3542 0.063 Uiso 1 1 calc R U . . .
H18C H 0.7228 0.4275 0.2472 0.063 Uiso 1 1 calc R U . . .
C13 C 0.79930(10) 0.9281(5) 0.5228(3) 0.0338(9) Uani 1 1 d . . . . .
C16 C 0.83402(12) 0.8623(6) 0.4390(5) 0.0522(12) Uani 1 1 d . . . . .
H16A H 0.8260 0.8987 0.3612 0.078 Uiso 1 1 calc R U . . .
H16B H 0.8368 0.7250 0.4433 0.078 Uiso 1 1 calc R U . . .
H16C H 0.8613 0.9211 0.4591 0.078 Uiso 1 1 calc R U . . .
C15 C 0.79592(11) 1.1429(5) 0.5148(4) 0.0434(10) Uani 1 1 d . . . . .
H15A H 0.7716 1.1864 0.5605 0.065 Uiso 1 1 calc R U . . .
H15B H 0.7917 1.1796 0.4349 0.065 Uiso 1 1 calc R U . . .
H15C H 0.8223 1.2001 0.5437 0.065 Uiso 1 1 calc R U . . .
C14 C 0.81092(17) 0.8732(8) 0.6442(5) 0.0641(15) Uani 1 1 d . . . . .
H14A H 0.8158 0.7370 0.6480 0.096 Uiso 1 1 calc R U . . .
H14B H 0.7875 0.9077 0.6957 0.096 Uiso 1 1 calc R U . . .
H14C H 0.8370 0.9396 0.6672 0.096 Uiso 1 1 calc R U . . .
C1 C 0.53281(11) 0.5560(5) 0.4564(3) 0.0298(7) Uani 1 1 d . . . . .
H1 H 0.5387 0.4533 0.4067 0.036 Uiso 1 1 calc R U . . .
C2 C 0.49126(9) 0.6105(4) 0.4920(4) 0.0277(6) Uani 1 1 d . . . . .
C3 C 0.49809(11) 0.7624(5) 0.5615(3) 0.0289(7) Uani 1 1 d . . . . .
H3 H 0.4767 0.8338 0.5992 0.035 Uiso 1 1 calc R U . . .
C8 C 0.56572(11) 0.9294(4) 0.6218(3) 0.0267(7) Uani 1 1 d . . . . .
C9 C 0.54303(13) 1.0769(5) 0.6887(4) 0.0427(10) Uani 1 1 d . . . . .
H9A H 0.5640 1.1604 0.7247 0.064 Uiso 1 1 calc R U . . .
H9B H 0.5255 1.0170 0.7478 0.064 Uiso 1 1 calc R U . . .
H9C H 0.5247 1.1503 0.6377 0.064 Uiso 1 1 calc R U . . .
C4 C 0.44953(11) 0.5138(5) 0.4641(4) 0.0341(9) Uani 1 1 d . . . . .
C5 C 0.45125(13) 0.4300(6) 0.3435(5) 0.0486(11) Uani 1 1 d . . . . .
H5A H 0.4731 0.3313 0.3406 0.073 Uiso 1 1 calc R U . . .
H5B H 0.4584 0.5293 0.2886 0.073 Uiso 1 1 calc R U . . .
H5C H 0.4234 0.3758 0.3242 0.073 Uiso 1 1 calc R U . . .
C7 C 0.41255(12) 0.6561(6) 0.4700(4) 0.0444(10) Uani 1 1 d . . . . .
H7A H 0.4183 0.7609 0.4177 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4100 0.7043 0.5480 0.067 Uiso 1 1 calc R U . . .
H7C H 0.3859 0.5939 0.4479 0.067 Uiso 1 1 calc R U . . .
C6 C 0.44215(16) 0.3573(8) 0.5518(6) 0.079(2) Uani 1 1 d . . . . .
H6A H 0.4413 0.4118 0.6286 0.118 Uiso 1 1 calc R U . . .
H6B H 0.4655 0.2655 0.5471 0.118 Uiso 1 1 calc R U . . .
H6C H 0.4149 0.2944 0.5357 0.118 Uiso 1 1 calc R U . . .
Cu1 Cu 0.62416(2) 0.72051(6) 0.49862(6) 0.02603(14) Uani 1 1 d . . . . .
F1 F 0.63436(9) 0.4675(4) 0.6475(2) 0.0593(8) Uani 1 1 d . . . . .
F4 F 0.65769(10) 0.1898(3) 0.7180(3) 0.0636(8) Uani 1 1 d . . . . .
F3 F 0.70021(10) 0.3602(5) 0.6043(3) 0.0820(11) Uani 1 1 d . . . . .
F2 F 0.68522(10) 0.4551(4) 0.7826(3) 0.0734(9) Uani 1 1 d . . . . .
N5 N 0.70676(8) 0.6515(4) 0.4244(2) 0.0258(6) Uani 1 1 d . . . . .
N4 N 0.68602(8) 0.7765(3) 0.4924(3) 0.0264(5) Uani 1 1 d . . . . .
N6 N 0.64224(9) 0.5259(4) 0.3888(3) 0.0288(6) Uani 1 1 d . . . . .
H6 H 0.6237 0.4527 0.3539 0.035 Uiso 1 1 calc R U . . .
N2 N 0.54095(8) 0.7933(4) 0.5669(3) 0.0253(6) Uani 1 1 d . . . . .
N1 N 0.56221(8) 0.6663(3) 0.5012(3) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.60567(9) 0.9143(4) 0.6071(3) 0.0269(6) Uani 1 1 d . . . . .
H3A H 0.6240 0.9865 0.6434 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
F8 B2 1.385(5) . ?
F8 Cu1 2.554(3) . ?
B2 F7 1.362(5) . ?
B2 F6 1.381(5) . ?
B2 F5 1.396(5) . ?
B1 F3 1.361(5) . ?
B1 F2 1.362(5) . ?
B1 F1 1.377(5) . ?
B1 F4 1.391(5) . ?
C12 N5 1.368(4) . ?
C12 C11 1.369(5) . ?
C12 H12 0.9500 . ?
C11 C10 1.417(4) . ?
C11 C13 1.512(4) . ?
C10 N4 1.322(4) . ?
C10 H10 0.9500 . ?
C17 N6 1.256(5) . ?
C17 N5 1.407(4) . ?
C17 C18 1.485(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C13 C14 1.518(6) . ?
C13 C15 1.532(5) . ?
C13 C16 1.538(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 N1 1.318(4) . ?
C1 C2 1.420(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.368(5) . ?
C2 C4 1.512(4) . ?
C3 N2 1.361(4) . ?
C3 H3 0.9500 . ?
C8 N3 1.267(4) . ?
C8 N2 1.396(4) . ?
C8 C9 1.488(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 C6 1.530(6) . ?
C4 C5 1.534(6) . ?
C4 C7 1.538(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
Cu1 N3 1.960(3) . ?
Cu1 N6 1.971(3) . ?
Cu1 N1 1.977(2) . ?
Cu1 N4 1.978(3) . ?
Cu1 F1 2.525(3) . ?
N5 N4 1.358(4) . ?
N6 H6 0.8800 . ?
N2 N1 1.360(4) . ?
N3 H3A 0.8800 . ?

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
B2 F8 Cu1 134.8(2) . . ?
F7 B2 F6 110.2(4) . . ?
F7 B2 F8 110.5(3) . . ?
F6 B2 F8 110.2(4) . . ?
F7 B2 F5 108.2(4) . . ?
F6 B2 F5 107.7(3) . . ?
F8 B2 F5 109.9(3) . . ?
F3 B1 F2 111.0(4) . . ?
F3 B1 F1 110.9(4) . . ?
F2 B1 F1 110.2(3) . . ?
F3 B1 F4 108.8(3) . . ?
F2 B1 F4 106.5(4) . . ?
F1 B1 F4 109.4(3) . . ?
N5 C12 C11 107.4(3) . . ?
N5 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?
C12 C11 C10 104.5(3) . . ?
C12 C11 C13 128.2(3) . . ?
C10 C11 C13 127.3(3) . . ?
N4 C10 C11 111.5(3) . . ?
N4 C10 H10 124.2 . . ?
C11 C10 H10 124.2 . . ?
N6 C17 N5 115.0(3) . . ?
N6 C17 C18 127.5(3) . . ?
N5 C17 C18 117.6(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C13 C14 108.8(3) . . ?
C11 C13 C15 110.2(3) . . ?
C14 C13 C15 109.3(4) . . ?
C11 C13 C16 109.8(3) . . ?
C14 C13 C16 110.5(4) . . ?
C15 C13 C16 108.2(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C1 C2 111.1(3) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C3 C2 C1 104.3(3) . . ?
C3 C2 C4 128.5(3) . . ?
C1 C2 C4 127.2(3) . . ?
N2 C3 C2 108.0(3) . . ?
N2 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
N3 C8 N2 115.3(3) . . ?
N3 C8 C9 127.0(3) . . ?
N2 C8 C9 117.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C4 C6 108.4(3) . . ?
C2 C4 C5 110.2(3) . . ?
C6 C4 C5 110.0(4) . . ?
C2 C4 C7 110.0(3) . . ?
C6 C4 C7 109.5(4) . . ?
C5 C4 C7 108.8(3) . . ?
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 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 Cu1 N6 179.47(14) . . ?
N3 Cu1 N1 80.64(12) . . ?
N6 Cu1 N1 98.91(12) . . ?
N3 Cu1 N4 99.90(12) . . ?
N6 Cu1 N4 80.54(12) . . ?
N1 Cu1 N4 178.69(18) . . ?
N3 Cu1 F1 95.10(11) . . ?
N6 Cu1 F1 85.17(11) . . ?
N1 Cu1 F1 88.58(12) . . ?
N4 Cu1 F1 92.56(11) . . ?
N3 Cu1 F8 82.03(11) . . ?
N6 Cu1 F8 97.70(12) . . ?
N1 Cu1 F8 91.33(11) . . ?
N4 Cu1 F8 87.57(11) . . ?
F1 Cu1 F8 177.10(11) . . ?
B1 F1 Cu1 133.2(3) . . ?
N4 N5 C12 111.0(3) . . ?
N4 N5 C17 116.9(3) . . ?
C12 N5 C17 132.1(3) . . ?
C10 N4 N5 105.5(3) . . ?
C10 N4 Cu1 143.4(3) . . ?
N5 N4 Cu1 111.00(19) . . ?
C17 N6 Cu1 116.3(3) . . ?
C17 N6 H6 121.9 . . ?
Cu1 N6 H6 121.9 . . ?
N1 N2 C3 110.4(3) . . ?
N1 N2 C8 116.6(3) . . ?
C3 N2 C8 132.9(3) . . ?
C1 N1 N2 106.2(3) . . ?
C1 N1 Cu1 142.6(3) . . ?
N2 N1 Cu1 111.1(2) . . ?
C8 N3 Cu1 116.0(2) . . ?
C8 N3 H3A 122.0 . . ?
Cu1 N3 H3A 122.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 F8 B2 F7 -85.1(5) . . . . ?
Cu1 F8 B2 F6 37.0(5) . . . . ?
Cu1 F8 B2 F5 155.5(3) . . . . ?
N5 C12 C11 C10 0.3(4) . . . . ?
N5 C12 C11 C13 178.0(3) . . . . ?
C12 C11 C10 N4 0.0(4) . . . . ?
C13 C11 C10 N4 -177.7(4) . . . . ?
C12 C11 C13 C14 -104.7(5) . . . . ?
C10 C11 C13 C14 72.5(5) . . . . ?
C12 C11 C13 C15 135.5(4) . . . . ?
C10 C11 C13 C15 -47.3(5) . . . . ?
C12 C11 C13 C16 16.4(6) . . . . ?
C10 C11 C13 C16 -166.5(4) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
N1 C1 C2 C4 -176.7(4) . . . . ?
C1 C2 C3 N2 -0.6(4) . . . . ?
C4 C2 C3 N2 176.2(4) . . . . ?
C3 C2 C4 C6 -90.1(5) . . . . ?
C1 C2 C4 C6 86.0(5) . . . . ?
C3 C2 C4 C5 149.5(4) . . . . ?
C1 C2 C4 C5 -34.4(5) . . . . ?
C3 C2 C4 C7 29.6(6) . . . . ?
C1 C2 C4 C7 -154.3(4) . . . . ?
F3 B1 F1 Cu1 -27.6(5) . . . . ?
F2 B1 F1 Cu1 95.7(4) . . . . ?
F4 B1 F1 Cu1 -147.6(3) . . . . ?
C11 C12 N5 N4 -0.5(4) . . . . ?
C11 C12 N5 C17 -178.7(4) . . . . ?
N6 C17 N5 N4 3.6(5) . . . . ?
C18 C17 N5 N4 -175.8(3) . . . . ?
N6 C17 N5 C12 -178.4(4) . . . . ?
C18 C17 N5 C12 2.2(6) . . . . ?
C11 C10 N4 N5 -0.3(4) . . . . ?
C11 C10 N4 Cu1 176.7(3) . . . . ?
C12 N5 N4 C10 0.5(4) . . . . ?
C17 N5 N4 C10 179.0(3) . . . . ?
C12 N5 N4 Cu1 -177.6(2) . . . . ?
C17 N5 N4 Cu1 0.9(4) . . . . ?
N5 C17 N6 Cu1 -6.3(4) . . . . ?
C18 C17 N6 Cu1 173.0(3) . . . . ?
C2 C3 N2 N1 0.9(4) . . . . ?
C2 C3 N2 C8 178.2(4) . . . . ?
N3 C8 N2 N1 -2.5(5) . . . . ?
C9 C8 N2 N1 176.4(3) . . . . ?
N3 C8 N2 C3 -179.7(4) . . . . ?
C9 C8 N2 C3 -0.8(6) . . . . ?
C2 C1 N1 N2 0.4(4) . . . . ?
C2 C1 N1 Cu1 -174.2(3) . . . . ?
C3 N2 N1 C1 -0.8(4) . . . . ?
C8 N2 N1 C1 -178.6(3) . . . . ?
C3 N2 N1 Cu1 175.7(2) . . . . ?
C8 N2 N1 Cu1 -2.1(4) . . . . ?
N2 C8 N3 Cu1 6.0(4) . . . . ?
C9 C8 N3 Cu1 -172.8(3) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.044

_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_1d'
_database_code_depnum_ccdc_archive 'CCDC 2388297'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Cl2 Cu N6 O8'
_chemical_formula_weight         508.77

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                   5.3447(3)
_cell_length_b                   13.7312(7)
_cell_length_c                   13.2253(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.850(4)
_cell_angle_gamma                90
_cell_volume                     969.39(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2911
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.457
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            13785
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         28.741
_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             2510
_reflns_number_gt                2019
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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+0.2908P] 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         2510
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
O1 O 0.2907(5) 1.01037(18) 0.15670(19) 0.0314(6) Uani 1 1 d . . . . .
Cu1 Cu 0.000000 1.000000 0.000000 0.01770(17) Uani 1 2 d S . P . .
Cl1 Cl 0.23212(13) 1.06318(5) 0.24851(5) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.3592(5) 1.0177(2) 0.33374(19) 0.0374(6) Uani 1 1 d . . . . .
O2 O -0.0324(4) 1.06145(17) 0.25878(17) 0.0260(5) Uani 1 1 d . . . . .
O4 O 0.3180(5) 1.16176(18) 0.2386(2) 0.0342(6) Uani 1 1 d . . . . .
N1 N 0.1028(5) 0.86271(17) -0.01738(19) 0.0189(5) Uani 1 1 d . . . . .
N2 N -0.0371(5) 0.80167(18) 0.03803(19) 0.0178(5) Uani 1 1 d . . . . .
N3 N -0.2414(4) 0.93582(18) 0.08504(18) 0.0194(5) Uani 1 1 d . . . . .
H3 H -0.358643 0.968995 0.114326 0.023 Uiso 1 1 calc R U . . .
C3 C 0.0307(6) 0.7067(2) 0.0236(2) 0.0245(6) Uani 1 1 d . . . . .
H3A H -0.040312 0.651069 0.053809 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2189(6) 0.7068(2) -0.0421(2) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.3611(7) 0.6209(3) -0.0796(3) 0.0342(8) Uani 1 1 d . . . . .
H4A H 0.414365 0.579390 -0.022250 0.051 Uiso 1 1 calc R U . . .
H4B H 0.508816 0.643778 -0.113732 0.051 Uiso 1 1 calc R U . . .
H4C H 0.253138 0.583481 -0.127418 0.051 Uiso 1 1 calc R U . . .
C1 C 0.2567(6) 0.8054(2) -0.0659(2) 0.0211(6) Uani 1 1 d . . . . .
H1 H 0.377090 0.828043 -0.110830 0.025 Uiso 1 1 calc R U . . .
C5 C -0.2207(5) 0.8443(2) 0.0959(2) 0.0178(6) Uani 1 1 d . . . . .
C6 C -0.3620(6) 0.7802(3) 0.1632(2) 0.0260(7) Uani 1 1 d . . . . .
H6A H -0.481147 0.819389 0.199836 0.039 Uiso 1 1 calc R U . . .
H6B H -0.244843 0.748000 0.211767 0.039 Uiso 1 1 calc R U . . .
H6C H -0.453227 0.730940 0.122408 0.039 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
O1 Cl1 1.461(2) . ?
O1 Cu1 2.532(2) . ?
Cu1 N3 1.962(2) . ?
Cu1 N3 1.962(2) 3_575 ?
Cu1 N1 1.980(2) 3_575 ?
Cu1 N1 1.980(2) . ?
Cl1 O2 1.427(2) . ?
Cl1 O3 1.430(3) . ?
Cl1 O4 1.437(3) . ?
N1 C1 1.326(4) . ?
N1 N2 1.361(3) . ?
N2 C3 1.370(4) . ?
N2 C5 1.402(4) . ?
N3 C5 1.268(4) . ?
N3 H3 0.8800 . ?
C3 C2 1.361(5) . ?
C3 H3A 0.9500 . ?
C2 C1 1.407(4) . ?
C2 C4 1.501(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C1 H1 0.9500 . ?
C5 C6 1.485(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
Cl1 O1 Cu1 124.04(13) . . ?
N3 Cu1 N3 180.00(10) . 3_575 ?
N3 Cu1 N1 99.61(10) . 3_575 ?
N3 Cu1 N1 80.40(10) 3_575 3_575 ?
N3 Cu1 N1 80.39(10) . . ?
N3 Cu1 N1 99.61(10) 3_575 . ?
N1 Cu1 N1 180.00(4) 3_575 . ?
N3 Cu1 O1 87.16(9) . . ?
N3 Cu1 O1 92.85(9) 3_575 . ?
N1 Cu1 O1 90.80(9) 3_575 . ?
N1 Cu1 O1 89.20(9) . . ?
O2 Cl1 O3 110.58(16) . . ?
O2 Cl1 O4 110.29(15) . . ?
O3 Cl1 O4 109.97(17) . . ?
O2 Cl1 O1 108.97(14) . . ?
O3 Cl1 O1 108.98(16) . . ?
O4 Cl1 O1 107.99(16) . . ?
C1 N1 N2 105.4(2) . . ?
C1 N1 Cu1 143.4(2) . . ?
N2 N1 Cu1 111.14(18) . . ?
N1 N2 C3 110.8(2) . . ?
N1 N2 C5 117.0(2) . . ?
C3 N2 C5 132.2(3) . . ?
C5 N3 Cu1 117.0(2) . . ?
C5 N3 H3 121.5 . . ?
Cu1 N3 H3 121.5 . . ?
C2 C3 N2 107.3(3) . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
C3 C2 C1 105.2(3) . . ?
C3 C2 C4 127.8(3) . . ?
C1 C2 C4 127.0(3) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C1 C2 111.3(3) . . ?
N1 C1 H1 124.3 . . ?
C2 C1 H1 124.3 . . ?
N3 C5 N2 114.3(3) . . ?
N3 C5 C6 127.7(3) . . ?
N2 C5 C6 118.0(3) . . ?
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 . . ?

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 O1 Cl1 O2 30.4(2) . . . . ?
Cu1 O1 Cl1 O3 151.19(18) . . . . ?
Cu1 O1 Cl1 O4 -89.37(19) . . . . ?
C1 N1 N2 C3 0.0(3) . . . . ?
Cu1 N1 N2 C3 178.4(2) . . . . ?
C1 N1 N2 C5 -178.9(2) . . . . ?
Cu1 N1 N2 C5 -0.4(3) . . . . ?
N1 N2 C3 C2 0.3(3) . . . . ?
C5 N2 C3 C2 178.9(3) . . . . ?
N2 C3 C2 C1 -0.4(3) . . . . ?
N2 C3 C2 C4 178.2(3) . . . . ?
N2 N1 C1 C2 -0.2(3) . . . . ?
Cu1 N1 C1 C2 -177.8(3) . . . . ?
C3 C2 C1 N1 0.4(4) . . . . ?
C4 C2 C1 N1 -178.2(3) . . . . ?
Cu1 N3 C5 N2 -4.7(3) . . . . ?
Cu1 N3 C5 C6 173.7(2) . . . . ?
N1 N2 C5 N3 3.3(4) . . . . ?
C3 N2 C5 N3 -175.2(3) . . . . ?
N1 N2 C5 C6 -175.3(3) . . . . ?
C3 N2 C5 C6 6.2(5) . . . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_1a'
_database_code_depnum_ccdc_archive 'CCDC 2388296'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cl4 Cu N6 O8'
_chemical_formula_weight         549.61

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'
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      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                   6.5992(3)
_cell_length_b                   8.3622(4)
_cell_length_c                   9.3885(5)
_cell_angle_alpha                81.900(3)
_cell_angle_beta                 74.576(3)
_cell_angle_gamma                74.932(3)
_cell_volume                     480.83(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2769
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.67

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             293
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.745
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            6162
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         28.760
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2450
_reflns_number_gt                2131
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0455P)²+0.3916P] 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         2450
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.6956(3) 0.7213(2) 0.83720(19) 0.0306(4) Uani 1 1 d . . . . .
N3 N 0.4347(3) 0.4410(2) 0.8241(2) 0.0230(4) Uani 1 1 d . . . . .
H3 H 0.311045 0.481440 0.803467 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 1.32537(9) 0.01890(8) 0.84343(8) 0.03568(17) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 1.000000 0.02158(12) Uani 1 2 d S . P . .
Cl2 Cl 0.84678(8) 0.70345(6) 0.69405(6) 0.02138(13) Uani 1 1 d . . . . .
N1 N 0.7694(3) 0.3333(2) 0.9270(2) 0.0225(4) Uani 1 1 d . . . . .
O2 O 1.0500(3) 0.6064(4) 0.7153(2) 0.0667(8) Uani 1 1 d . . . . .
O4 O 0.7757(4) 0.6185(3) 0.6030(2) 0.0532(6) Uani 1 1 d . . . . .
O3 O 0.8673(4) 0.8616(3) 0.6231(2) 0.0574(7) Uani 1 1 d . . . . .
N2 N 0.7681(3) 0.2763(2) 0.7982(2) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.5864(4) 0.2876(3) 0.5980(3) 0.0299(5) Uani 1 1 d . . . . .
H5A H 0.445527 0.327329 0.578468 0.045 Uiso 1 1 calc R U . . .
H5B H 0.626105 0.168525 0.600555 0.045 Uiso 1 1 calc R U . . .
H5C H 0.689759 0.332532 0.521195 0.045 Uiso 1 1 calc R U . . .
C2 C 1.0773(4) 0.1499(3) 0.8462(3) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.9557(4) 0.1647(3) 0.7470(3) 0.0266(5) Uani 1 1 d . . . . .
H3A H 0.993294 0.109449 0.661066 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5832(4) 0.3407(3) 0.7428(2) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.9563(4) 0.2580(3) 0.9566(3) 0.0254(5) Uani 1 1 d . . . . .
H1 H 1.001707 0.273809 1.038121 0.030 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
O1 Cl2 1.4455(17) . ?
O1 Cu1 2.6123(17) . ?
N3 C4 1.266(3) . ?
N3 Cu1 1.9688(19) . ?
N3 H3 0.8600 . ?
Cl1 C2 1.713(2) . ?
Cu1 N1 1.9762(19) 2_667 ?
Cu1 N1 1.9762(19) . ?
Cl2 O3 1.417(2) . ?
Cl2 O4 1.419(2) . ?
Cl2 O2 1.424(2) . ?
N1 C1 1.313(3) . ?
N1 N2 1.363(3) . ?
N2 C3 1.358(3) . ?
N2 C4 1.403(3) . ?
C5 C4 1.481(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C3 1.356(3) . ?
C2 C1 1.406(3) . ?
C3 H3A 0.9300 . ?
C1 H1 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 O1 Cu1 127.71(10) . . ?
C4 N3 Cu1 116.86(16) . . ?
C4 N3 H3 121.6 . . ?
Cu1 N3 H3 121.6 . . ?
N3 Cu1 N3 180.0 . 2_667 ?
N3 Cu1 N1 99.64(8) . 2_667 ?
N3 Cu1 N1 80.36(8) 2_667 2_667 ?
N3 Cu1 N1 80.36(8) . . ?
N3 Cu1 N1 99.64(8) 2_667 . ?
N1 Cu1 N1 180.0 2_667 . ?
N3 Cu1 O1 90.39(7) . . ?
N3 Cu1 O1 89.61(7) 2_667 . ?
N1 Cu1 O1 93.49(7) 2_667 . ?
N1 Cu1 O1 86.51(7) . . ?
O3 Cl2 O4 109.18(15) . . ?
O3 Cl2 O2 110.56(17) . . ?
O4 Cl2 O2 107.98(17) . . ?
O3 Cl2 O1 110.25(12) . . ?
O4 Cl2 O1 110.39(12) . . ?
O2 Cl2 O1 108.45(12) . . ?
C1 N1 N2 106.42(18) . . ?
C1 N1 Cu1 142.35(17) . . ?
N2 N1 Cu1 111.21(13) . . ?
C3 N2 N1 110.85(19) . . ?
C3 N2 C4 132.1(2) . . ?
N1 N2 C4 117.05(18) . . ?
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 . . ?
C3 C2 C1 106.8(2) . . ?
C3 C2 Cl1 127.1(2) . . ?
C1 C2 Cl1 126.1(2) . . ?
C2 C3 N2 106.3(2) . . ?
C2 C3 H3A 126.9 . . ?
N2 C3 H3A 126.9 . . ?
N3 C4 N2 114.3(2) . . ?
N3 C4 C5 128.3(2) . . ?
N2 C4 C5 117.3(2) . . ?
N1 C1 C2 109.7(2) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 Cl2 O3 162.75(15) . . . . ?
Cu1 O1 Cl2 O4 42.04(18) . . . . ?
Cu1 O1 Cl2 O2 -76.07(19) . . . . ?
C1 N1 N2 C3 -0.1(2) . . . . ?
Cu1 N1 N2 C3 178.60(14) . . . . ?
C1 N1 N2 C4 -179.51(19) . . . . ?
Cu1 N1 N2 C4 -0.8(2) . . . . ?
C1 C2 C3 N2 -0.7(3) . . . . ?
Cl1 C2 C3 N2 176.69(17) . . . . ?
N1 N2 C3 C2 0.5(2) . . . . ?
C4 N2 C3 C2 179.8(2) . . . . ?
Cu1 N3 C4 N2 4.8(3) . . . . ?
Cu1 N3 C4 C5 -173.69(19) . . . . ?
C3 N2 C4 N3 178.1(2) . . . . ?
N1 N2 C4 N3 -2.6(3) . . . . ?
C3 N2 C4 C5 -3.2(4) . . . . ?
N1 N2 C4 C5 176.12(19) . . . . ?
N2 N1 C1 C2 -0.4(2) . . . . ?
Cu1 N1 C1 C2 -178.36(19) . . . . ?
C3 C2 C1 N1 0.7(3) . . . . ?
Cl1 C2 C1 N1 -176.73(17) . . . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_2a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2388303'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl6 Cu N8 O8'
_chemical_formula_weight         672.54

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'
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'
O O 0.0106 0.0060 '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                   13.4847(7)
_cell_length_b                   10.0717(4)
_cell_length_c                   19.0149(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.77
_cell_angle_gamma                90
_cell_volume                     2414.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4143
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             1340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.625
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            3161
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         28.834
_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             3161
_reflns_number_gt                2696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)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         3161
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
O1 O 0.3198(2) 0.3393(2) 0.7401(2) 0.0480(8) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.36486(5) 0.750000 0.01869(14) Uani 1 2 d S T P . .
Cl2 Cl 0.28629(10) 0.01410(11) 0.50066(6) 0.0534(3) Uani 1 1 d . . . . .
Cl3 Cl 0.24180(7) 0.39920(8) 0.76345(6) 0.0315(2) Uani 1 1 d . . . . .
Cl1 Cl 0.50767(11) 0.72894(10) 0.98552(5) 0.0486(3) Uani 1 1 d . . . . .
N2 N 0.6035(3) 0.6093(3) 0.82876(18) 0.0261(7) Uani 1 1 d . . . . .
H2 H 0.638611 0.616347 0.798965 0.031 Uiso 1 1 calc R U . . .
N1 N 0.5400(2) 0.5067(2) 0.82879(14) 0.0202(6) Uani 1 1 d . . . . .
N3 N 0.4615(3) 0.2243(2) 0.67050(14) 0.0213(6) Uani 1 1 d . . . . .
O4 O 0.1405(2) 0.3441(3) 0.72763(18) 0.0472(8) Uani 1 1 d . . . . .
N4 N 0.5289(3) 0.1289(3) 0.66695(18) 0.0240(6) Uani 1 1 d . . . . .
H4 H 0.593575 0.123027 0.697283 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6053(3) 0.6998(3) 0.8813(2) 0.0297(8) Uani 1 1 d . . . . .
H3 H 0.644166 0.778251 0.892165 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3700(3) 0.1987(3) 0.6148(2) 0.0275(8) Uani 1 1 d . . . . .
H4A H 0.308077 0.248095 0.603553 0.033 Uiso 1 1 calc R U . . .
O3 O 0.2429(2) 0.5401(2) 0.7501(2) 0.0475(7) Uani 1 1 d . . . . .
C5 C 0.3824(3) 0.0863(4) 0.57659(19) 0.0282(8) Uani 1 1 d . . . . .
C2 C 0.5386(3) 0.6530(3) 0.91523(19) 0.0237(7) Uani 1 1 d . . . . .
C6 C 0.4837(3) 0.0438(3) 0.6106(2) 0.0287(8) Uani 1 1 d . . . . .
H6 H 0.515254 -0.029564 0.597497 0.034 Uiso 1 1 calc R U . . .
C1 C 0.4997(3) 0.5330(3) 0.88164(18) 0.0228(7) Uani 1 1 d . . . . .
H1 H 0.452575 0.478837 0.894121 0.027 Uiso 1 1 calc R U . . .
O2 O 0.2749(3) 0.3755(4) 0.84365(18) 0.0689(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 Cl3 1.414(3) . ?
O1 Cu1 2.383(3) . ?
Cu1 N3 2.000(2) . ?
Cu1 N3 2.000(2) 2_656 ?
Cu1 N1 2.001(2) . ?
Cu1 N1 2.001(2) 2_656 ?
Cl2 C5 1.722(4) . ?
Cl3 O4 1.407(3) . ?
Cl3 O3 1.443(2) . ?
Cl3 O2 1.449(3) . ?
Cl1 C2 1.715(3) . ?
N2 N1 1.342(4) . ?
N2 C3 1.345(4) . ?
N2 H2 0.8600 . ?
N1 C1 1.328(4) . ?
N3 C4 1.335(4) . ?
N3 N4 1.341(4) . ?
N4 C6 1.338(4) . ?
N4 H4 0.8600 . ?
C3 C2 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.357(5) . ?
C2 C1 1.381(5) . ?
C6 H6 0.9300 . ?
C1 H1 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
Cl3 O1 Cu1 141.29(18) . . ?
N3 Cu1 N3 89.92(14) . 2_656 ?
N3 Cu1 N1 179.10(12) . . ?
N3 Cu1 N1 90.61(9) 2_656 . ?
N3 Cu1 N1 90.60(9) . 2_656 ?
N3 Cu1 N1 179.11(12) 2_656 2_656 ?
N1 Cu1 N1 88.88(14) . 2_656 ?
N3 Cu1 O1 83.09(12) . . ?
N3 Cu1 O1 88.15(12) 2_656 . ?
N1 Cu1 O1 97.65(12) . . ?
N1 Cu1 O1 91.20(12) 2_656 . ?
N3 Cu1 O1 88.15(12) . 2_656 ?
N3 Cu1 O1 83.09(12) 2_656 2_656 ?
N1 Cu1 O1 91.20(12) . 2_656 ?
N1 Cu1 O1 97.65(12) 2_656 2_656 ?
O1 Cu1 O1 167.62(12) . 2_656 ?
O4 Cl3 O1 112.50(18) . . ?
O4 Cl3 O3 111.81(17) . . ?
O1 Cl3 O3 108.00(17) . . ?
O4 Cl3 O2 109.2(2) . . ?
O1 Cl3 O2 105.9(2) . . ?
O3 Cl3 O2 109.2(2) . . ?
N1 N2 C3 111.4(3) . . ?
N1 N2 H2 124.3 . . ?
C3 N2 H2 124.3 . . ?
C1 N1 N2 106.2(3) . . ?
C1 N1 Cu1 129.4(2) . . ?
N2 N1 Cu1 123.5(2) . . ?
C4 N3 N4 105.9(3) . . ?
C4 N3 Cu1 130.9(2) . . ?
N4 N3 Cu1 123.1(2) . . ?
C6 N4 N3 112.0(3) . . ?
C6 N4 H4 124.0 . . ?
N3 N4 H4 124.0 . . ?
N2 C3 C2 106.0(3) . . ?
N2 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
N3 C4 C5 109.0(3) . . ?
N3 C4 H4A 125.5 . . ?
C5 C4 H4A 125.5 . . ?
C6 C5 C4 107.2(3) . . ?
C6 C5 Cl2 126.7(3) . . ?
C4 C5 Cl2 126.1(3) . . ?
C3 C2 C1 106.8(3) . . ?
C3 C2 Cl1 126.8(3) . . ?
C1 C2 Cl1 126.4(3) . . ?
N4 C6 C5 106.0(3) . . ?
N4 C6 H6 127.0 . . ?
C5 C6 H6 127.0 . . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 Cl3 O4 170.7(3) . . . . ?
Cu1 O1 Cl3 O3 46.8(4) . . . . ?
Cu1 O1 Cl3 O2 -70.1(4) . . . . ?
C3 N2 N1 C1 0.7(4) . . . . ?
C3 N2 N1 Cu1 171.0(2) . . . . ?
C4 N3 N4 C6 0.4(4) . . . . ?
Cu1 N3 N4 C6 177.6(2) . . . . ?
N1 N2 C3 C2 -0.9(4) . . . . ?
N4 N3 C4 C5 -0.4(4) . . . . ?
Cu1 N3 C4 C5 -177.4(2) . . . . ?
N3 C4 C5 C6 0.3(4) . . . . ?
N3 C4 C5 Cl2 179.7(3) . . . . ?
N2 C3 C2 C1 0.8(4) . . . . ?
N2 C3 C2 Cl1 -178.7(3) . . . . ?
N3 N4 C6 C5 -0.2(4) . . . . ?
C4 C5 C6 N4 -0.1(4) . . . . ?
Cl2 C5 C6 N4 -179.5(3) . . . . ?
N2 N1 C1 C2 -0.2(4) . . . . ?
Cu1 N1 C1 C2 -169.7(2) . . . . ?
C3 C2 C1 N1 -0.4(4) . . . . ?
Cl1 C2 C1 N1 179.1(3) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2388301'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 Cl2 Cu N8 O8'
_chemical_formula_weight         590.88

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      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                   8.8912(5)
_cell_length_b                   8.8939(6)
_cell_length_c                   9.1265(6)
_cell_angle_alpha                90.491(4)
_cell_angle_beta                 117.756(4)
_cell_angle_gamma                110.978(4)
_cell_volume                     582.75(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2767
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.01

_exptl_crystal_description       block
_exptl_crystal_colour            blue-purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_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  0.784
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            10047
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2880
_reflns_number_gt                2359
_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       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_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+0.1526P] 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         2880
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.892
_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 1.000000 0.500000 0.01687(15) Uani 1 2 d S . P . .
Cl1 Cl 0.67744(9) 0.70069(7) 0.70773(8) 0.02321(17) Uani 1 1 d . . . . .
N1 N 0.4042(3) 0.8974(3) 0.2605(3) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.3314(3) 0.7323(3) 0.2034(3) 0.0200(4) Uani 1 1 d . . . . .
H3 H 0.333362 0.660050 0.268717 0.024 Uiso 1 1 calc R U . . .
O4 O 0.7198(3) 0.5734(2) 0.6599(3) 0.0305(5) Uani 1 1 d . . . . .
O2 O 0.8474(3) 0.8347(3) 0.8329(3) 0.0340(5) Uani 1 1 d . . . . .
O1 O 0.5884(3) 0.7652(2) 0.5603(2) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.5554(3) 0.6352(3) 0.7747(3) 0.0334(5) Uani 1 1 d . . . . .
C3 C 0.2556(4) 0.6927(3) 0.0339(3) 0.0227(5) Uani 1 1 d . . . . .
C6 C -0.0029(4) 0.7077(3) 0.4825(3) 0.0246(5) Uani 1 1 d . . . . .
H6 H -0.079133 0.629016 0.516199 0.029 Uiso 1 1 calc R U . . .
C7 C -0.0561(4) 0.8012(3) 0.3641(3) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.0965(3) 0.8946(3) 0.3575(3) 0.0211(4) Uani 1 1 d . . . . .
H7 H 0.098231 0.964856 0.290318 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3714(4) 0.9611(3) 0.1239(3) 0.0246(5) Uani 1 1 d . . . . .
H1 H 0.406412 1.075434 0.124739 0.030 Uiso 1 1 calc R U . . .
C2 C 0.2791(4) 0.8389(4) -0.0208(3) 0.0275(6) Uani 1 1 d . . . . .
H2 H 0.240219 0.853119 -0.133971 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1720(4) 0.5210(4) -0.0621(4) 0.0330(7) Uani 1 1 d . . . . .
H4A H 0.120182 0.444308 -0.004575 0.050 Uiso 1 1 calc R U . . .
H4B H 0.268140 0.496202 -0.068150 0.050 Uiso 1 1 calc R U . . .
H4C H 0.072637 0.509331 -0.177021 0.050 Uiso 1 1 calc R U . . .
N3 N 0.2470(3) 0.8679(3) 0.4662(3) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.1865(4) 0.7532(3) 0.5422(3) 0.0230(5) Uani 1 1 d . . . . .
H5 H 0.261717 0.708659 0.625447 0.028 Uiso 1 1 calc R U . . .
C8 C -0.2407(4) 0.8067(4) 0.2551(4) 0.0340(7) Uani 1 1 d . . . . .
H8A H -0.256156 0.821965 0.143510 0.051 Uiso 1 1 calc R U . . .
H8B H -0.247274 0.898736 0.308059 0.051 Uiso 1 1 calc R U . . .
H8C H -0.339855 0.703129 0.242264 0.051 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 1.997(2) . ?
Cu1 N3 1.997(2) 2_676 ?
Cu1 N1 2.002(2) . ?
Cu1 N1 2.002(2) 2_676 ?
Cu1 O1 2.4647(18) . ?
Cl1 O3 1.436(2) . ?
Cl1 O4 1.437(2) . ?
Cl1 O2 1.445(2) . ?
Cl1 O1 1.4536(19) . ?
N1 C1 1.324(3) . ?
N1 N2 1.356(3) . ?
N2 C3 1.349(3) . ?
N2 H3 0.8800 . ?
C3 C2 1.378(4) . ?
C3 C4 1.486(4) . ?
C6 C7 1.379(4) . ?
C6 C5 1.397(4) . ?
C6 H6 0.9500 . ?
C7 N4 1.343(4) . ?
C7 C8 1.491(4) . ?
N4 N3 1.352(3) . ?
N4 H7 0.8800 . ?
C1 C2 1.388(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N3 C5 1.334(3) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.0 . 2_676 ?
N3 Cu1 N1 88.08(9) . . ?
N3 Cu1 N1 91.92(9) 2_676 . ?
N3 Cu1 N1 91.92(9) . 2_676 ?
N3 Cu1 N1 88.08(9) 2_676 2_676 ?
N1 Cu1 N1 180.0 . 2_676 ?
N3 Cu1 O1 91.70(8) . . ?
N3 Cu1 O1 88.30(8) 2_676 . ?
N1 Cu1 O1 82.59(8) . . ?
N1 Cu1 O1 97.41(8) 2_676 . ?
O3 Cl1 O4 109.85(13) . . ?
O3 Cl1 O2 110.05(14) . . ?
O4 Cl1 O2 109.83(13) . . ?
O3 Cl1 O1 109.76(13) . . ?
O4 Cl1 O1 109.41(12) . . ?
O2 Cl1 O1 107.91(12) . . ?
C1 N1 N2 105.3(2) . . ?
C1 N1 Cu1 131.17(18) . . ?
N2 N1 Cu1 122.89(16) . . ?
C3 N2 N1 111.6(2) . . ?
C3 N2 H3 124.2 . . ?
N1 N2 H3 124.2 . . ?
Cl1 O1 Cu1 137.58(12) . . ?
N2 C3 C2 106.3(2) . . ?
N2 C3 C4 123.3(3) . . ?
C2 C3 C4 130.4(3) . . ?
C7 C6 C5 105.5(2) . . ?
C7 C6 H6 127.2 . . ?
C5 C6 H6 127.2 . . ?
N4 C7 C6 106.6(2) . . ?
N4 C7 C8 122.4(3) . . ?
C6 C7 C8 131.0(3) . . ?
C7 N4 N3 112.0(2) . . ?
C7 N4 H7 124.0 . . ?
N3 N4 H7 124.0 . . ?
N1 C1 C2 111.2(2) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C3 C2 C1 105.6(2) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 N3 N4 105.4(2) . . ?
C5 N3 Cu1 132.53(18) . . ?
N4 N3 Cu1 121.85(16) . . ?
N3 C5 C6 110.5(2) . . ?
N3 C5 H5 124.8 . . ?
C6 C5 H5 124.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.6(3) . . . . ?
Cu1 N1 N2 C3 172.26(17) . . . . ?
O3 Cl1 O1 Cu1 70.2(2) . . . . ?
O4 Cl1 O1 Cu1 -169.23(16) . . . . ?
O2 Cl1 O1 Cu1 -49.8(2) . . . . ?
N1 N2 C3 C2 -0.6(3) . . . . ?
N1 N2 C3 C4 177.7(2) . . . . ?
C5 C6 C7 N4 0.1(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C6 C7 N4 N3 -0.4(3) . . . . ?
C8 C7 N4 N3 -179.4(2) . . . . ?
N2 N1 C1 C2 -0.3(3) . . . . ?
Cu1 N1 C1 C2 -171.04(19) . . . . ?
N2 C3 C2 C1 0.4(3) . . . . ?
C4 C3 C2 C1 -177.7(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C7 N4 N3 C5 0.5(3) . . . . ?
C7 N4 N3 Cu1 -175.17(16) . . . . ?
N4 N3 C5 C6 -0.4(3) . . . . ?
Cu1 N3 C5 C6 174.60(18) . . . . ?
C7 C6 C5 N3 0.2(3) . . . . ?

_refine_diff_density_max         0.984
_refine_diff_density_min         -1.182
_refine_diff_density_rms         0.104

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2c
_database_code_depnum_ccdc_archive 'CCDC 2388300'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica, Taipei
Taiwan
;
_audit_update_record             
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Cl2 Cu I5 N10 O8'
_chemical_formula_weight         1232.32

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.9446(7)
_cell_length_b                   23.069(2)
_cell_length_c                   15.8266(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.659(3)
_cell_angle_gamma                90
_cell_volume                     3255.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9853
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.515
_exptl_crystal_F_000             3760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.631
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.085
_exptl_absorpt_correction_T_max  0.237
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_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            70701
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_max         27.896
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             7621
_reflns_number_gt                7283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.973

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_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+0.3836P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7621
_refine_ls_number_parameters     371
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_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
C1 C 0.3026(12) 0.7535(5) 0.6381(8) 0.042(2) Uani 1 1 d . . . . .
H1 H 0.230911 0.727783 0.658686 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3101(12) 0.8112(4) 0.6555(8) 0.042(3) Uani 1 1 d . . . . .
H2A H 0.248631 0.832742 0.690342 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4257(9) 0.8315(4) 0.6119(6) 0.0288(17) Uani 1 1 d . . . . .
C4 C 0.2304(9) 0.6915(4) 0.4228(6) 0.0307(18) Uani 1 1 d . . . . .
H4A H 0.163157 0.700547 0.464386 0.037 Uiso 1 1 calc R U . . .
C5 C 0.2005(9) 0.6995(4) 0.3356(6) 0.0304(17) Uani 1 1 d . . . . .
H5 H 0.110411 0.713599 0.306967 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3290(9) 0.6826(4) 0.2998(5) 0.0253(15) Uani 1 1 d . . . . .
C7 C 0.5389(13) 0.6462(5) 0.7405(6) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.435286 0.641330 0.747778 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6479(14) 0.6481(5) 0.8062(6) 0.041(2) Uani 1 1 d . . . . .
H8A H 0.636201 0.645765 0.865202 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7788(12) 0.6543(4) 0.7666(6) 0.0318(18) Uani 1 1 d . . . . .
C10 C 0.6760(9) 0.5540(4) 0.5190(6) 0.0315(18) Uani 1 1 d . . . . .
H10 H 0.769871 0.572440 0.532650 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6594(11) 0.4959(4) 0.4976(6) 0.0332(19) Uani 1 1 d . . . . .
H11 H 0.736392 0.467915 0.493156 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5072(11) 0.4876(4) 0.4844(6) 0.0291(17) Uani 1 1 d . . . . .
C13 C 0.8897(12) 0.5469(5) 0.3242(10) 0.049(3) Uani 1 1 d . . . . .
H13 H 0.993392 0.538915 0.336325 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7891(15) 0.5107(6) 0.2850(9) 0.050(3) Uani 1 1 d . . . . .
H14 H 0.806377 0.473061 0.263341 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6524(10) 0.5410(4) 0.2830(6) 0.0304(17) Uani 1 1 d . . . . .
Cl1 Cl 0.81035(19) 0.74137(8) 0.46131(11) 0.0215(3) Uani 1 1 d . . . . .
Cl2 Cl 0.1182(2) 0.58661(8) 0.59186(15) 0.0271(4) Uani 1 1 d . . . . .
Cu1 Cu 0.48018(10) 0.65908(4) 0.55166(6) 0.01902(18) Uani 1 1 d . . . . .
I1 I 0.51028(7) 0.91430(2) 0.60441(6) 0.04449(19) Uani 1 1 d . . . . .
I2 I 0.38370(6) 0.68869(3) 0.17761(3) 0.03262(14) Uani 1 1 d . . . . .
I3 I 0.99315(8) 0.66424(4) 0.82230(5) 0.04579(19) Uani 1 1 d . . . . .
I4 I 0.38444(8) 0.41323(2) 0.46228(4) 0.03762(16) Uani 1 1 d . . . . .
I5 I 0.44283(8) 0.51474(3) 0.23511(4) 0.04129(17) Uani 1 1 d . . . . .
N1 N 0.4093(8) 0.7376(3) 0.5880(5) 0.0258(14) Uani 1 1 d . . . . .
N2 N 0.4845(7) 0.7860(3) 0.5727(5) 0.0231(13) Uani 1 1 d . . . . .
H2 H 0.561474 0.787846 0.541517 0.028 Uiso 1 1 calc R U . . .
N3 N 0.3663(8) 0.6693(3) 0.4389(4) 0.0231(13) Uani 1 1 d . . . . .
N4 N 0.4262(8) 0.6652(3) 0.3635(4) 0.0225(13) Uani 1 1 d . . . . .
H4 H 0.517431 0.652600 0.357007 0.027 Uiso 1 1 calc R U . . .
N5 N 0.5936(8) 0.6517(3) 0.6657(5) 0.0247(13) Uani 1 1 d . . . . .
N6 N 0.7427(9) 0.6561(3) 0.6830(5) 0.0277(14) Uani 1 1 d . . . . .
H6 H 0.807769 0.659585 0.644529 0.033 Uiso 1 1 calc R U . . .
N7 N 0.5452(8) 0.5805(3) 0.5180(4) 0.0238(13) Uani 1 1 d . . . . .
N8 N 0.4418(7) 0.5391(3) 0.4965(4) 0.0223(12) Uani 1 1 d . . . . .
H8 H 0.344312 0.545125 0.491220 0.027 Uiso 1 1 calc R U . . .
N9 N 0.8197(10) 0.5966(4) 0.3439(7) 0.041(2) Uani 1 1 d . . . . .
H9 H 0.864739 0.626545 0.369320 0.050 Uiso 1 1 calc R U . . .
N10 N 0.6720(9) 0.5941(3) 0.3192(5) 0.0290(15) Uani 1 1 d . . . . .
O1 O 0.7281(7) 0.6985(3) 0.5052(5) 0.0315(13) Uani 1 1 d . . . . .
O2 O 0.7223(7) 0.7945(3) 0.4571(4) 0.0300(12) Uani 1 1 d . . . . .
O3 O 0.9523(6) 0.7527(3) 0.5062(5) 0.0343(14) Uani 1 1 d . . . . .
O4 O 0.8314(10) 0.7219(4) 0.3769(4) 0.0456(19) Uani 1 1 d . . . . .
O5 O 0.2579(7) 0.6156(3) 0.6143(5) 0.0360(15) Uani 1 1 d . . . . .
O6 O 0.0010(8) 0.6278(4) 0.5813(7) 0.052(2) Uani 1 1 d . . . . .
O7 O 0.0860(13) 0.5462(4) 0.6570(8) 0.064(3) Uani 1 1 d . . . . .
O8 O 0.1299(9) 0.5568(5) 0.5133(7) 0.061(3) 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
C1 N1 1.340(11) . ?
C1 C2 1.360(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(13) . ?
C2 H2A 0.9500 . ?
C3 N2 1.348(10) . ?
C3 I1 2.062(9) . ?
C4 N3 1.324(11) . ?
C4 C5 1.396(13) . ?
C4 H4A 0.9500 . ?
C5 C6 1.378(12) . ?
C5 H5 0.9500 . ?
C6 N4 1.338(11) . ?
C6 I2 2.039(8) . ?
C7 N5 1.324(13) . ?
C7 C8 1.366(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(16) . ?
C8 H8A 0.9500 . ?
C9 N6 1.338(12) . ?
C9 I3 2.057(10) . ?
C10 N7 1.318(11) . ?
C10 C11 1.389(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(14) . ?
C11 H11 0.9500 . ?
C12 N8 1.345(11) . ?
C12 I4 2.053(9) . ?
C13 C14 1.342(19) . ?
C13 N9 1.355(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(14) . ?
C14 H14 0.9500 . ?
C15 N10 1.357(12) . ?
C15 I5 2.056(9) . ?
Cl1 O3 1.428(6) . ?
Cl1 O4 1.437(6) . ?
Cl1 O1 1.443(7) . ?
Cl1 O2 1.456(6) . ?
Cl2 O6 1.415(8) . ?
Cl2 O8 1.433(9) . ?
Cl2 O7 1.436(10) . ?
Cl2 O5 1.437(6) . ?
Cu1 N7 1.990(7) . ?
Cu1 N3 1.995(7) . ?
Cu1 N5 2.004(7) . ?
Cu1 N1 2.018(7) . ?
Cu1 O5 2.502(7) . ?
Cu1 O1 2.560(6) . ?
N1 N2 1.336(10) . ?
N2 H2 0.8800 . ?
N3 N4 1.351(10) . ?
N4 H4 0.8800 . ?
N5 N6 1.343(10) . ?
N6 H6 0.8800 . ?
N7 N8 1.353(10) . ?
N8 H8 0.8800 . ?
N9 N10 1.348(12) . ?
N9 H9 0.8800 . ?

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 C1 C2 111.2(9) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C1 C2 C3 105.0(8) . . ?
C1 C2 H2A 127.5 . . ?
C3 C2 H2A 127.5 . . ?
N2 C3 C2 107.7(8) . . ?
N2 C3 I1 122.5(6) . . ?
C2 C3 I1 129.8(6) . . ?
N3 C4 C5 109.9(8) . . ?
N3 C4 H4A 125.1 . . ?
C5 C4 H4A 125.1 . . ?
C6 C5 C4 105.7(7) . . ?
C6 C5 H5 127.2 . . ?
C4 C5 H5 127.2 . . ?
N4 C6 C5 106.7(7) . . ?
N4 C6 I2 122.9(6) . . ?
C5 C6 I2 130.0(6) . . ?
N5 C7 C8 112.6(10) . . ?
N5 C7 H7 123.7 . . ?
C8 C7 H7 123.7 . . ?
C7 C8 C9 103.8(9) . . ?
C7 C8 H8A 128.1 . . ?
C9 C8 H8A 128.1 . . ?
N6 C9 C8 107.8(9) . . ?
N6 C9 I3 124.2(7) . . ?
C8 C9 I3 127.9(7) . . ?
N7 C10 C11 111.6(8) . . ?
N7 C10 H10 124.2 . . ?
C11 C10 H10 124.2 . . ?
C12 C11 C10 104.8(7) . . ?
C12 C11 H11 127.6 . . ?
C10 C11 H11 127.6 . . ?
N8 C12 C11 107.1(8) . . ?
N8 C12 I4 122.0(7) . . ?
C11 C12 I4 130.7(7) . . ?
C14 C13 N9 109.2(10) . . ?
C14 C13 H13 125.4 . . ?
N9 C13 H13 125.4 . . ?
C13 C14 C15 104.4(10) . . ?
C13 C14 H14 127.8 . . ?
C15 C14 H14 127.8 . . ?
N10 C15 C14 110.9(9) . . ?
N10 C15 I5 120.3(7) . . ?
C14 C15 I5 128.7(8) . . ?
O3 Cl1 O4 110.0(5) . . ?
O3 Cl1 O1 110.7(4) . . ?
O4 Cl1 O1 110.1(5) . . ?
O3 Cl1 O2 108.9(4) . . ?
O4 Cl1 O2 109.4(5) . . ?
O1 Cl1 O2 107.7(4) . . ?
O6 Cl2 O8 109.0(6) . . ?
O6 Cl2 O7 109.3(7) . . ?
O8 Cl2 O7 110.2(8) . . ?
O6 Cl2 O5 109.7(5) . . ?
O8 Cl2 O5 108.4(5) . . ?
O7 Cl2 O5 110.2(6) . . ?
N7 Cu1 N3 90.4(3) . . ?
N7 Cu1 N5 91.5(3) . . ?
N3 Cu1 N5 178.0(3) . . ?
N7 Cu1 N1 178.2(3) . . ?
N3 Cu1 N1 90.0(3) . . ?
N5 Cu1 N1 88.1(3) . . ?
N7 Cu1 O5 90.0(3) . . ?
N3 Cu1 O5 92.2(3) . . ?
N5 Cu1 O5 88.3(3) . . ?
N1 Cu1 O5 88.2(3) . . ?
N7 Cu1 O1 88.2(3) . . ?
N3 Cu1 O1 95.3(3) . . ?
N5 Cu1 O1 84.4(3) . . ?
N1 Cu1 O1 93.6(2) . . ?
O5 Cu1 O1 172.4(2) . . ?
N2 N1 C1 105.8(7) . . ?
N2 N1 Cu1 121.5(5) . . ?
C1 N1 Cu1 132.0(7) . . ?
N1 N2 C3 110.2(7) . . ?
N1 N2 H2 124.9 . . ?
C3 N2 H2 124.9 . . ?
C4 N3 N4 106.3(7) . . ?
C4 N3 Cu1 127.7(6) . . ?
N4 N3 Cu1 124.9(5) . . ?
C6 N4 N3 111.4(7) . . ?
C6 N4 H4 124.3 . . ?
N3 N4 H4 124.3 . . ?
C7 N5 N6 104.9(8) . . ?
C7 N5 Cu1 128.1(7) . . ?
N6 N5 Cu1 126.8(6) . . ?
C9 N6 N5 110.9(8) . . ?
C9 N6 H6 124.6 . . ?
N5 N6 H6 124.6 . . ?
C10 N7 N8 105.3(7) . . ?
C10 N7 Cu1 134.2(6) . . ?
N8 N7 Cu1 120.1(5) . . ?
C12 N8 N7 111.2(7) . . ?
C12 N8 H8 124.4 . . ?
N7 N8 H8 124.4 . . ?
N10 N9 C13 110.9(9) . . ?
N10 N9 H9 124.5 . . ?
C13 N9 H9 124.5 . . ?
N9 N10 C15 104.5(8) . . ?
Cl1 O1 Cu1 150.4(4) . . ?
Cl2 O5 Cu1 142.3(4) . . ?

_refine_diff_density_max         2.472
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.142

