# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2163634'
loop_
_audit_author_name
_audit_author_address
'Ni Jianling'
;Jiangsu University of Science and Technology
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H17 Cu I2 N2'
_chemical_formula_sum            'C8 H17 Cu I2 N2'
_chemical_formula_weight         458.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3656(3)
_cell_length_b                   11.6981(3)
_cell_length_c                   18.3655(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2656.64(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.258
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27078
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.729
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2456
_reflns_number_total             2821
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+4.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0546
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B), C6(H6A,H6B), C3(H3A,H3B),
 C7(H7A,H7B)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.08223(2) 0.23358(2) 0.37067(2) 0.04431(8) Uani 1 1 d . . . . .
I2 I -0.17095(2) 0.01156(2) 0.45597(2) 0.03994(8) Uani 1 1 d . . . . .
Cu1 Cu 0.01730(4) 0.11152(4) 0.48156(3) 0.04264(12) Uani 1 1 d . . . . .
N1 N -0.0230(2) 0.2370(2) 0.56526(15) 0.0337(6) Uani 1 1 d . . . . .
N2 N -0.0708(2) 0.3825(2) 0.66530(15) 0.0355(6) Uani 1 1 d . . . . .
C2 C -0.1050(3) 0.2647(3) 0.68742(19) 0.0388(8) Uani 1 1 d . . . . .
H2A H -0.182589 0.262749 0.695035 0.047 Uiso 1 1 calc R . . . .
H2B H -0.069861 0.243647 0.732709 0.047 Uiso 1 1 calc R . . . .
C5 C -0.0999(3) 0.3228(3) 0.53768(19) 0.0471(9) Uani 1 1 d . . . . .
H5A H -0.165810 0.284802 0.522429 0.057 Uiso 1 1 calc R . . . .
H5B H -0.068967 0.360343 0.495430 0.057 Uiso 1 1 calc R . . . .
C4 C 0.0492(3) 0.3808(3) 0.6511(2) 0.0479(9) Uani 1 1 d . . . . .
H4A H 0.087193 0.358645 0.695087 0.057 Uiso 1 1 calc R . . . .
H4B H 0.073390 0.456584 0.637282 0.057 Uiso 1 1 calc R . . . .
C1 C -0.0737(4) 0.1802(3) 0.62764(19) 0.0487(10) Uani 1 1 d . . . . .
H1A H -0.023979 0.124156 0.647445 0.058 Uiso 1 1 calc R . . . .
H1B H -0.137918 0.140045 0.611325 0.058 Uiso 1 1 calc R . . . .
C6 C -0.1271(3) 0.4126(3) 0.59530(18) 0.0392(8) Uani 1 1 d . . . . .
H6A H -0.103808 0.487463 0.578865 0.047 Uiso 1 1 calc R . . . .
H6B H -0.204698 0.415015 0.603039 0.047 Uiso 1 1 calc R . . . .
C3 C 0.0749(3) 0.2960(4) 0.5901(3) 0.0579(11) Uani 1 1 d . . . . .
H3A H 0.107287 0.336578 0.549477 0.069 Uiso 1 1 calc R . . . .
H3B H 0.126847 0.240232 0.607487 0.069 Uiso 1 1 calc R . . . .
C7 C -0.0937(3) 0.4685(3) 0.7249(2) 0.0481(9) Uani 1 1 d . . . . .
H7A H -0.058544 0.442854 0.769158 0.058 Uiso 1 1 calc R . . . .
H7B H -0.061245 0.540909 0.711267 0.058 Uiso 1 1 calc R . . . .
C8 C -0.2110(4) 0.4883(4) 0.7410(3) 0.0724(14) Uani 1 1 d . . . . .
H8A H -0.245212 0.522437 0.699367 0.109 Uiso 1 1 calc GR . . . .
H8B H -0.217734 0.538574 0.782062 0.109 Uiso 1 1 calc GR . . . .
H8C H -0.245322 0.416701 0.751811 0.109 Uiso 1 1 calc GR . . . .


_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 Cu1 2.6136(5) . ?
I2 Cu1 2.6455(5) 5_556 ?
I2 Cu1 2.6471(5) . ?
Cu1 Cu1 2.7293(9) 5_556 ?
Cu1 N1 2.183(3) . ?
N1 C5 1.472(4) . ?
N1 C1 1.465(4) . ?
N1 C3 1.467(4) . ?
N2 C2 1.498(4) . ?
N2 C4 1.506(5) . ?
N2 C6 1.504(4) . ?
N2 C7 1.513(5) . ?
C2 C1 1.527(5) . ?
C5 C6 1.529(5) . ?
C4 C3 1.529(6) . ?
C7 C8 1.499(6) . ?

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
Cu1 I2 Cu1 62.085(18) 5_556 . ?
I1 Cu1 I2 114.496(18) . 5_556 ?
I1 Cu1 I2 111.905(18) . . ?
I1 Cu1 Cu1 139.80(3) . 5_556 ?
I2 Cu1 I2 117.916(18) 5_556 . ?
I2 Cu1 Cu1 58.929(17) . 5_556 ?
I2 Cu1 Cu1 58.986(17) 5_556 5_556 ?
N1 Cu1 I1 104.56(7) . . ?
N1 Cu1 I2 102.78(7) . . ?
N1 Cu1 I2 102.98(7) . 5_556 ?
N1 Cu1 Cu1 115.61(8) . 5_556 ?
C5 N1 Cu1 111.3(2) . . ?
C1 N1 Cu1 110.1(2) . . ?
C1 N1 C5 107.6(3) . . ?
C1 N1 C3 108.9(3) . . ?
C3 N1 Cu1 110.3(2) . . ?
C3 N1 C5 108.6(3) . . ?
C2 N2 C4 108.2(3) . . ?
C2 N2 C6 108.4(3) . . ?
C2 N2 C7 111.3(3) . . ?
C4 N2 C7 108.6(3) . . ?
C6 N2 C4 108.1(3) . . ?
C6 N2 C7 112.1(3) . . ?
N2 C2 C1 109.2(3) . . ?
N1 C5 C6 111.9(3) . . ?
N2 C4 C3 109.9(3) . . ?
N1 C1 C2 112.2(3) . . ?
N2 C6 C5 109.2(3) . . ?
N1 C3 C4 111.1(3) . . ?
C8 C7 N2 115.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2163635'
loop_
_audit_author_name
_audit_author_address
'Ni Jianling'
;Jiangsu University of Science and Technology
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H32 Cu2 F2 I4 N4'
_chemical_formula_sum            'C16 H32 Cu2 F2 I4 N4'
_chemical_formula_weight         953.13
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.4735(8)
_cell_length_b                   8.6042(11)
_cell_length_c                   10.7737(11)
_cell_angle_alpha                80.277(2)
_cell_angle_beta                 83.715(2)
_cell_angle_gamma                75.290(2)
_cell_volume                     658.84(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7943
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.324
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.825
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4742
_reflns_number_total             5052
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.506
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.252
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     403
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.2723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.52(7)
 0.48(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.005 and
sigma for terminal atoms of 0.01
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C15(H15A,H15B),
 C14(H14A,H14B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.91206(11) 0.59632(9) 0.48846(7) 0.0313(3) Uani 1 1 d . U . . .
I3 I 1.47260(11) 0.20815(10) 0.49982(7) 0.0310(3) Uani 1 1 d . U . . .
I2 I 1.38471(15) 0.58949(13) 0.19664(10) 0.0392(4) Uani 1 1 d . U . . .
I4 I 0.99951(14) 0.21481(13) 0.79193(10) 0.0386(4) Uani 1 1 d . U . . .
Cu1 Cu 1.1845(4) 0.3718(3) 0.6212(2) 0.0371(6) Uani 1 1 d . U . . .
Cu2 Cu 1.2032(4) 0.4292(3) 0.3694(2) 0.0345(6) Uani 1 1 d . U . . .
N3 N 1.306(2) 0.534(2) 0.6998(13) 0.0268(17) Uani 1 1 d . U . . .
C5 C 1.358(2) 0.6582(18) 0.5988(14) 0.032(2) Uani 1 1 d . U . . .
H5A H 1.454397 0.604492 0.541761 0.038 Uiso 1 1 calc R . . . .
H5B H 1.251008 0.711482 0.550791 0.038 Uiso 1 1 calc R . . . .
C4 C 1.153(2) 0.6365(17) 0.7719(12) 0.028(2) Uani 1 1 d . U . . .
H4A H 1.086240 0.568371 0.830224 0.034 Uiso 1 1 calc R . . . .
H4B H 1.066158 0.708378 0.714344 0.034 Uiso 1 1 calc R . . . .
C1 C 1.4494(17) 0.4522(17) 0.7862(12) 0.031(2) Uani 1 1 d . U . . .
H1A H 1.539245 0.368736 0.746910 0.037 Uiso 1 1 calc R . . . .
H1B H 1.394003 0.400001 0.862261 0.037 Uiso 1 1 calc R . . . .
C2 C 1.550(3) 0.576(2) 0.8216(17) 0.030(2) Uani 1 1 d . U . . .
H2A H 1.572488 0.551715 0.910610 0.036 Uiso 1 1 calc R . . . .
H2B H 1.668081 0.568939 0.772911 0.036 Uiso 1 1 calc R . . . .
C3 C 1.239(2) 0.740(2) 0.8474(16) 0.027(2) Uani 1 1 d . U . . .
H3A H 1.162230 0.849984 0.842769 0.032 Uiso 1 1 calc R . . . .
H3B H 1.244036 0.691959 0.935530 0.032 Uiso 1 1 calc R . . . .
C6 C 1.425(2) 0.783(2) 0.6477(16) 0.031(2) Uani 1 1 d . U . . .
H6A H 1.344525 0.889768 0.624115 0.037 Uiso 1 1 calc R . . . .
H6B H 1.549357 0.784487 0.611685 0.037 Uiso 1 1 calc R . . . .
N4 N 1.425(2) 0.743(2) 0.7921(14) 0.0260(17) Uani 1 1 d . U . . .
C7 C 1.484(3) 0.875(3) 0.842(2) 0.036(2) Uani 1 1 d . U . . .
H7A H 1.460711 0.861109 0.933522 0.043 Uiso 1 1 calc R . . . .
H7B H 1.407486 0.979461 0.808768 0.043 Uiso 1 1 calc R . . . .
C8 C 1.689(2) 0.877(2) 0.8099(19) 0.045(3) Uani 1 1 d . U . . .
H8A H 1.729222 0.846434 0.726910 0.054 Uiso 1 1 calc R . . . .
H8B H 1.706547 0.984880 0.810381 0.054 Uiso 1 1 calc R . . . .
F2 F 1.791(2) 0.7637(18) 0.9036(13) 0.058(3) Uani 1 1 d . U . . .
N2 N 0.959(2) 0.059(2) 0.1998(15) 0.0284(18) Uani 1 1 d . U . . .
N1 N 1.079(2) 0.269(2) 0.2882(14) 0.0279(17) Uani 1 1 d . U . . .
C10 C 1.161(2) 0.068(2) 0.1426(18) 0.032(2) Uani 1 1 d . U . . .
H10A H 1.246485 -0.037703 0.159991 0.039 Uiso 1 1 calc R . . . .
H10B H 1.161174 0.099615 0.051847 0.039 Uiso 1 1 calc R . . . .
C11 C 0.977(2) 0.012(2) 0.3375(16) 0.033(2) Uani 1 1 d . U . . .
H11A H 1.083346 -0.079076 0.353567 0.039 Uiso 1 1 calc R . . . .
H11B H 0.867079 -0.019319 0.378240 0.039 Uiso 1 1 calc R . . . .
C15 C 0.907(3) -0.069(3) 0.1393(19) 0.036(2) Uani 1 1 d . U . . .
H15A H 0.922975 -0.040613 0.048380 0.044 Uiso 1 1 calc R . . . .
H15B H 0.994040 -0.171931 0.162636 0.044 Uiso 1 1 calc R . . . .
C14 C 0.9065(19) 0.3496(18) 0.2228(13) 0.035(2) Uani 1 1 d . U . . .
H14A H 0.932434 0.430656 0.153597 0.042 Uiso 1 1 calc R . . . .
H14B H 0.813560 0.404294 0.281384 0.042 Uiso 1 1 calc R . . . .
C9 C 1.219(2) 0.1879(19) 0.2007(14) 0.034(2) Uani 1 1 d . U . . .
H9A H 1.329426 0.133886 0.245302 0.041 Uiso 1 1 calc R . . . .
H9B H 1.252646 0.269031 0.134370 0.041 Uiso 1 1 calc R . . . .
C12 C 1.005(2) 0.1663(17) 0.3918(14) 0.032(2) Uani 1 1 d . U . . .
H12A H 0.887291 0.226008 0.426505 0.038 Uiso 1 1 calc R . . . .
H12B H 1.090302 0.131085 0.458413 0.038 Uiso 1 1 calc R . . . .
C13 C 0.831(3) 0.225(3) 0.1716(17) 0.032(2) Uani 1 1 d . U . . .
H13A H 0.708181 0.223602 0.210717 0.039 Uiso 1 1 calc R . . . .
H13B H 0.821976 0.254294 0.081197 0.039 Uiso 1 1 calc R . . . .
C16 C 0.717(2) -0.092(2) 0.1717(18) 0.043(3) Uani 1 1 d . U . . .
H16A H 0.687224 -0.169829 0.235878 0.051 Uiso 1 1 calc R . . . .
F1 F 0.589(2) 0.0155(17) 0.0964(13) 0.055(3) Uani 1 1 d . U . . .
H16B H 0.718(13) -0.189(12) 0.131(9) 0.04(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.762(3) . ?
I1 Cu2 2.621(3) . ?
I3 Cu1 2.607(3) . ?
I3 Cu2 2.724(3) . ?
I2 Cu2 2.596(3) . ?
I4 Cu1 2.583(3) . ?
Cu1 Cu2 2.6685(10) . ?
Cu1 N3 2.165(17) . ?
Cu2 N1 2.179(17) . ?
N3 C5 1.49(2) . ?
N3 C4 1.49(2) . ?
N3 C1 1.46(2) . ?
C5 C6 1.49(2) . ?
C4 C3 1.59(2) . ?
C1 C2 1.56(3) . ?
C2 N4 1.51(2) . ?
C3 N4 1.45(2) . ?
C6 N4 1.54(2) . ?
N4 C7 1.52(3) . ?
C7 C8 1.54(3) . ?
C8 F2 1.42(2) . ?
N2 C10 1.58(2) . ?
N2 C11 1.48(2) . ?
N2 C15 1.51(3) . ?
N2 C13 1.51(2) . ?
N1 C14 1.49(2) . ?
N1 C9 1.45(2) . ?
N1 C12 1.46(2) . ?
C10 C9 1.47(3) . ?
C11 C12 1.60(2) . ?
C15 C16 1.48(3) . ?
C14 C13 1.53(3) . ?
C16 F1 1.38(2) . ?

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
Cu2 I1 Cu1 59.37(7) . . ?
Cu1 I3 Cu2 60.03(7) . . ?
I3 Cu1 I1 119.84(11) . . ?
I3 Cu1 Cu2 62.16(7) . . ?
I4 Cu1 I1 103.56(10) . . ?
I4 Cu1 I3 118.67(12) . . ?
I4 Cu1 Cu2 134.84(8) . . ?
Cu2 Cu1 I1 57.69(6) . . ?
N3 Cu1 I1 100.0(5) . . ?
N3 Cu1 I3 101.4(4) . . ?
N3 Cu1 I4 111.9(4) . . ?
N3 Cu1 Cu2 111.8(4) . . ?
I1 Cu2 I3 120.75(10) . . ?
I1 Cu2 Cu1 62.94(7) . . ?
I2 Cu2 I1 117.51(12) . . ?
I2 Cu2 I3 104.19(10) . . ?
I2 Cu2 Cu1 135.26(8) . . ?
Cu1 Cu2 I3 57.81(6) . . ?
N1 Cu2 I1 101.0(4) . . ?
N1 Cu2 I3 100.8(5) . . ?
N1 Cu2 I2 111.1(4) . . ?
N1 Cu2 Cu1 112.4(4) . . ?
C5 N3 Cu1 110.6(11) . . ?
C5 N3 C4 100.9(13) . . ?
C4 N3 Cu1 106.8(11) . . ?
C1 N3 Cu1 114.6(12) . . ?
C1 N3 C5 114.9(14) . . ?
C1 N3 C4 107.7(12) . . ?
C6 C5 N3 113.4(14) . . ?
N3 C4 C3 108.8(13) . . ?
N3 C1 C2 111.0(13) . . ?
N4 C2 C1 107.0(15) . . ?
N4 C3 C4 108.7(13) . . ?
C5 C6 N4 108.7(14) . . ?
C2 N4 C6 107.0(13) . . ?
C2 N4 C7 114.2(16) . . ?
C3 N4 C2 109.0(15) . . ?
C3 N4 C6 110.6(13) . . ?
C3 N4 C7 107.4(13) . . ?
C7 N4 C6 108.7(15) . . ?
N4 C7 C8 114.4(14) . . ?
F2 C8 C7 106.6(17) . . ?
C11 N2 C10 104.5(14) . . ?
C11 N2 C15 113.3(16) . . ?
C11 N2 C13 110.6(14) . . ?
C15 N2 C10 106.4(13) . . ?
C13 N2 C10 108.4(15) . . ?
C13 N2 C15 113.1(17) . . ?
C14 N1 Cu2 115.7(11) . . ?
C9 N1 Cu2 107.2(12) . . ?
C9 N1 C14 109.8(13) . . ?
C9 N1 C12 116.8(15) . . ?
C12 N1 Cu2 107.8(11) . . ?
C12 N1 C14 99.8(13) . . ?
C9 C10 N2 108.4(13) . . ?
N2 C11 C12 107.8(14) . . ?
C16 C15 N2 116.5(14) . . ?
N1 C14 C13 110.8(13) . . ?
N1 C9 C10 114.2(15) . . ?
N1 C12 C11 107.9(13) . . ?
N2 C13 C14 109.7(16) . . ?
F1 C16 C15 112.5(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.52(7)
2 0.48(7)

####################################################################### 
# 
# 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_2222
_database_code_depnum_ccdc_archive 'CCDC 2163639'
loop_
_audit_author_name
_audit_author_address
'Ni Jianling'
;Jiangsu University of Science and Technology
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H32 Br2 Cu2 I4 N4'
_chemical_formula_sum            'C16 H32 Br2 Cu2 I4 N4'
_chemical_formula_weight         1074.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1560(2)
_cell_length_b                   21.1757(5)
_cell_length_c                   8.8306(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.732(2)
_cell_angle_gamma                90
_cell_volume                     1416.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3711
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.691
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.520
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9386
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.808
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2378
_reflns_number_total             2769
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.359
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+5.2476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C4(H4A,H4B), C1(H1A,H1B), C5(H5A,H5B), C3(H3A,H3B),
 C7(H7A,H7B), C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.37653(6) 0.15977(2) 0.59273(5) 0.04859(14) Uani 1 1 d . . . . .
I2 I 0.76604(5) 0.00463(2) 0.70939(4) 0.04106(12) Uani 1 1 d . . . . .
Br1 Br 1.09579(9) 0.17372(4) -0.14223(8) 0.0548(2) Uani 1 1 d . . . . .
Cu1 Cu 0.50281(10) 0.06420(4) 0.48851(9) 0.04285(19) Uani 1 1 d . . . . .
N1 N 0.6291(6) 0.0986(2) 0.3256(5) 0.0325(10) Uani 1 1 d . . . . .
N2 N 0.7641(6) 0.1386(2) 0.1227(5) 0.0318(10) Uani 1 1 d . . . . .
C6 C 0.7483(9) 0.0680(3) 0.1155(8) 0.0454(15) Uani 1 1 d . . . . .
H6A H 0.861178 0.049214 0.128441 0.054 Uiso 1 1 calc R . . . .
H6B H 0.662594 0.055120 0.010668 0.054 Uiso 1 1 calc R . . . .
C2 C 0.5834(8) 0.1664(3) 0.0837(7) 0.0452(15) Uani 1 1 d . . . . .
H2A H 0.511133 0.158822 -0.029905 0.054 Uiso 1 1 calc R . . . .
H2B H 0.592169 0.211589 0.102197 0.054 Uiso 1 1 calc R . . . .
C4 C 0.8765(9) 0.1578(3) 0.2926(7) 0.0503(17) Uani 1 1 d . . . . .
H4A H 0.897850 0.202973 0.296953 0.060 Uiso 1 1 calc R . . . .
H4B H 0.989393 0.136296 0.326564 0.060 Uiso 1 1 calc R . . . .
C1 C 0.4993(8) 0.1349(3) 0.1944(7) 0.0452(15) Uani 1 1 d . . . . .
H1A H 0.448205 0.167144 0.241427 0.054 Uiso 1 1 calc R . . . .
H1B H 0.405025 0.107044 0.129561 0.054 Uiso 1 1 calc R . . . .
C5 C 0.6893(9) 0.0454(3) 0.2530(7) 0.0424(14) Uani 1 1 d . . . . .
H5A H 0.594202 0.015065 0.209613 0.051 Uiso 1 1 calc R . . . .
H5B H 0.787073 0.024469 0.336468 0.051 Uiso 1 1 calc R . . . .
C3 C 0.7789(8) 0.1400(3) 0.4072(7) 0.0442(15) Uani 1 1 d . . . . .
H3A H 0.860325 0.118958 0.503096 0.053 Uiso 1 1 calc R . . . .
H3B H 0.737558 0.178148 0.442469 0.053 Uiso 1 1 calc R . . . .
C7 C 0.8342(7) 0.1626(3) -0.0043(7) 0.0383(13) Uani 1 1 d . . . . .
H7A H 0.771936 0.141493 -0.107083 0.046 Uiso 1 1 calc R . . . .
H7B H 0.810297 0.207495 -0.020586 0.046 Uiso 1 1 calc R . . . .
C8 C 1.0276(9) 0.1517(4) 0.0437(8) 0.060(2) Uani 1 1 d . . . . .
H8A H 1.055306 0.107817 0.073375 0.072 Uiso 1 1 calc R . . . .
H8B H 1.092541 0.177706 0.137240 0.072 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.5894(8) . ?
I2 Cu1 2.6275(8) . ?
I2 Cu1 2.6739(9) 3_656 ?
Br1 C8 1.975(6) . ?
Cu1 Cu1 2.7282(15) 3_656 ?
Cu1 N1 2.181(4) . ?
N1 C1 1.465(7) . ?
N1 C5 1.467(7) . ?
N1 C3 1.460(7) . ?
N2 C6 1.501(7) . ?
N2 C2 1.503(7) . ?
N2 C4 1.495(7) . ?
N2 C7 1.522(6) . ?
C6 C5 1.538(7) . ?
C2 C1 1.539(8) . ?
C4 C3 1.548(8) . ?
C7 C8 1.492(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I2 Cu1 61.94(3) . 3_656 ?
I1 Cu1 I2 108.69(3) . 3_656 ?
I1 Cu1 I2 115.76(3) . . ?
I1 Cu1 Cu1 137.10(4) . 3_656 ?
I2 Cu1 I2 118.06(3) . 3_656 ?
I2 Cu1 Cu1 59.87(3) . 3_656 ?
I2 Cu1 Cu1 58.20(3) 3_656 3_656 ?
N1 Cu1 I1 108.71(12) . . ?
N1 Cu1 I2 101.21(12) . . ?
N1 Cu1 I2 102.94(12) . 3_656 ?
N1 Cu1 Cu1 113.99(13) . 3_656 ?
C1 N1 Cu1 108.5(3) . . ?
C1 N1 C5 108.5(4) . . ?
C5 N1 Cu1 110.4(3) . . ?
C3 N1 Cu1 112.9(3) . . ?
C3 N1 C1 107.6(5) . . ?
C3 N1 C5 108.8(5) . . ?
C6 N2 C2 108.5(5) . . ?
C6 N2 C7 110.5(4) . . ?
C2 N2 C7 107.7(4) . . ?
C4 N2 C6 108.9(5) . . ?
C4 N2 C2 108.0(5) . . ?
C4 N2 C7 113.0(4) . . ?
N2 C6 C5 108.9(4) . . ?
N2 C2 C1 108.4(5) . . ?
N2 C4 C3 108.5(5) . . ?
N1 C1 C2 111.6(4) . . ?
N1 C5 C6 111.1(5) . . ?
N1 C3 C4 111.3(4) . . ?
C8 C7 N2 112.7(5) . . ?
C7 C8 Br1 108.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1111
_database_code_depnum_ccdc_archive 'CCDC 2163638'
loop_
_audit_author_name
_audit_author_address
'Ni Jianling'
;Jiangsu University of Science and Technology
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H32 Cl2 Cu2 I4 N4'
_chemical_formula_sum            'C16 H32 Cl2 Cu2 I4 N4'
_chemical_formula_weight         986.03
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0904(10)
_cell_length_b                   21.288(3)
_cell_length_c                   8.7689(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.327(8)
_cell_angle_gamma                90
_cell_volume                     1397.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.144
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.344
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11557
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.377
_diffrn_reflns_theta_min         2.885
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2028
_reflns_number_total             2564
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.865
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+9.0888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1122
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49845(16) 0.06347(6) 0.00841(13) 0.0464(3) Uani 1 1 d . . . . .
I1 I 0.22859(8) 0.00444(3) -0.21415(7) 0.0437(2) Uani 1 1 d . . . . .
I2 I 0.63040(9) 0.15594(3) -0.10077(7) 0.0532(2) Uani 1 1 d . . . . .
Cl1 Cl -0.0849(3) 0.17866(12) 0.6319(3) 0.0478(6) Uani 1 1 d . . . . .
N1 N 0.3741(9) 0.1001(3) 0.1715(8) 0.0339(15) Uani 1 1 d . . . . .
N2 N 0.2396(9) 0.1414(3) 0.3739(8) 0.0347(15) Uani 1 1 d . . . . .
C1 C 0.2189(12) 0.1399(5) 0.0848(10) 0.048(2) Uani 1 1 d . . . . .
H1A H 0.136098 0.117446 -0.009581 0.057 Uiso 1 1 calc R . . . .
H1B H 0.257166 0.177527 0.045131 0.057 Uiso 1 1 calc R . . . .
C2 C 0.3146(13) 0.0475(4) 0.2485(11) 0.042(2) Uani 1 1 d . . . . .
H2A H 0.410018 0.016864 0.291185 0.051 Uiso 1 1 calc R . . . .
H2B H 0.212510 0.026907 0.166401 0.051 Uiso 1 1 calc R . . . .
C3 C 0.1232(13) 0.1584(5) 0.2038(10) 0.052(3) Uani 1 1 d . . . . .
H3A H 0.099705 0.203230 0.196825 0.062 Uiso 1 1 calc R . . . .
H3B H 0.010032 0.136484 0.172239 0.062 Uiso 1 1 calc R . . . .
C4 C 0.2632(14) 0.0720(5) 0.3898(12) 0.051(2) Uani 1 1 d . . . . .
H4A H 0.152940 0.052352 0.384589 0.061 Uiso 1 1 calc R . . . .
H4B H 0.356222 0.061626 0.495244 0.061 Uiso 1 1 calc R . . . .
C5 C 0.5043(12) 0.1374(5) 0.3005(10) 0.043(2) Uani 1 1 d . . . . .
H5A H 0.554124 0.169055 0.250607 0.052 Uiso 1 1 calc R . . . .
H5B H 0.601189 0.110491 0.368050 0.052 Uiso 1 1 calc R . . . .
C6 C 0.4205(11) 0.1696(5) 0.4096(11) 0.050(3) Uani 1 1 d . . . . .
H6A H 0.495797 0.163661 0.524852 0.059 Uiso 1 1 calc R . . . .
H6B H 0.409136 0.214325 0.386880 0.059 Uiso 1 1 calc R . . . .
C7 C 0.1718(11) 0.1668(4) 0.5002(10) 0.043(2) Uani 1 1 d . . . . .
H7A H 0.240385 0.148138 0.606498 0.051 Uiso 1 1 calc R . . . .
H7B H 0.191852 0.211783 0.509956 0.051 Uiso 1 1 calc R . . . .
C8 C -0.0207(13) 0.1543(6) 0.4596(13) 0.064(3) Uani 1 1 d . . . . .
H8A H -0.044646 0.109865 0.438055 0.077 Uiso 1 1 calc R . . . .
H8B H -0.091582 0.177261 0.360716 0.077 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu1 2.707(3) 3_655 ?
Cu1 I1 2.6301(13) . ?
Cu1 I1 2.6822(14) 3_655 ?
Cu1 I2 2.5900(13) . ?
Cu1 N1 2.182(6) . ?
Cl1 C8 1.849(9) . ?
N1 C1 1.465(11) . ?
N1 C2 1.480(11) . ?
N1 C5 1.454(10) . ?
N2 C3 1.476(11) . ?
N2 C4 1.489(11) . ?
N2 C6 1.501(11) . ?
N2 C7 1.511(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C3 1.567(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C4 1.541(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.528(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.484(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
I1 Cu1 Cu1 58.42(5) 3_655 3_655 ?
I1 Cu1 Cu1 60.32(4) . 3_655 ?
I1 Cu1 I1 118.74(5) . 3_655 ?
I2 Cu1 Cu1 136.46(7) . 3_655 ?
I2 Cu1 I1 115.56(5) . . ?
I2 Cu1 I1 107.97(5) . 3_655 ?
N1 Cu1 Cu1 114.1(2) . 3_655 ?
N1 Cu1 I1 101.41(18) . . ?
N1 Cu1 I1 102.63(18) . 3_655 ?
N1 Cu1 I2 109.15(19) . . ?
Cu1 I1 Cu1 61.26(5) . 3_655 ?
C1 N1 Cu1 112.6(5) . . ?
C1 N1 C2 108.2(7) . . ?
C2 N1 Cu1 109.8(5) . . ?
C5 N1 Cu1 109.1(5) . . ?
C5 N1 C1 108.2(7) . . ?
C5 N1 C2 108.9(6) . . ?
C3 N2 C4 110.4(7) . . ?
C3 N2 C6 108.0(7) . . ?
C3 N2 C7 112.5(6) . . ?
C4 N2 C6 107.3(7) . . ?
C4 N2 C7 110.8(7) . . ?
C6 N2 C7 107.5(6) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C3 110.0(7) . . ?
H1A C1 H1B 108.2 . . ?
C3 C1 H1A 109.7 . . ?
C3 C1 H1B 109.7 . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C4 110.1(7) . . ?
H2A C2 H2B 108.1 . . ?
C4 C2 H2A 109.6 . . ?
C4 C2 H2B 109.6 . . ?
N2 C3 C1 108.9(7) . . ?
N2 C3 H3A 109.9 . . ?
N2 C3 H3B 109.9 . . ?
C1 C3 H3A 109.9 . . ?
C1 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C2 108.9(7) . . ?
N2 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C2 C4 H4A 109.9 . . ?
C2 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N1 C5 C6 111.6(7) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N2 C6 C5 108.6(7) . . ?
N2 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 N2 113.6(7) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
Cl1 C8 H8A 109.6 . . ?
Cl1 C8 H8B 109.6 . . ?
C7 C8 Cl1 110.4(7) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C3 173.7(6) . . . . ?
Cu1 N1 C2 C4 168.2(6) . . . . ?
Cu1 N1 C5 C6 174.6(6) . . . . ?
N1 C1 C3 N2 11.7(11) . . . . ?
N1 C2 C4 N2 16.0(10) . . . . ?
N1 C5 C6 N2 12.6(11) . . . . ?
N2 C7 C8 Cl1 173.3(7) . . . . ?
C1 N1 C2 C4 -68.6(9) . . . . ?
C1 N1 C5 C6 51.8(9) . . . . ?
C2 N1 C1 C3 52.1(10) . . . . ?
C2 N1 C5 C6 -65.6(10) . . . . ?
C3 N2 C4 C2 49.2(10) . . . . ?
C3 N2 C6 C5 -66.7(9) . . . . ?
C3 N2 C7 C8 48.5(11) . . . . ?
C4 N2 C3 C1 -64.7(10) . . . . ?
C4 N2 C6 C5 52.4(9) . . . . ?
C4 N2 C7 C8 -75.7(10) . . . . ?
C5 N1 C1 C3 -65.7(9) . . . . ?
C5 N1 C2 C4 48.8(10) . . . . ?
C6 N2 C3 C1 52.3(10) . . . . ?
C6 N2 C4 C2 -68.3(9) . . . . ?
C6 N2 C7 C8 167.3(9) . . . . ?
C7 N2 C3 C1 170.8(8) . . . . ?
C7 N2 C4 C2 174.6(7) . . . . ?
C7 N2 C6 C5 171.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
