# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

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

data_180k
_database_code_depnum_ccdc_archive 'CCDC 1975152'
loop_
_audit_author_name
_audit_author_address
Wu
;Changzhou University
China
;
_audit_update_record             
;
2020-05-09 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Cu2 I2 N2'
_chemical_formula_weight         475.00

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'
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'

_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                   11.5103(4)
_cell_length_b                   4.24120(10)
_cell_length_c                   19.5894(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.446(3)
_cell_angle_gamma                90
_cell_volume                     956.28(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4378
_cell_measurement_theta_min      2.0650
_cell_measurement_theta_max      29.6400

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.299
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    10.842
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.02151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6581
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1672
_reflns_number_gt                1465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+2.1137P] 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         1672
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.67474(9) 0.1374(2) 0.20872(5) 0.0381(3) Uani 1 1 d . . . . .
Cu2 Cu 0.54460(8) -0.35046(19) 0.13890(5) 0.0328(3) Uani 1 1 d . . . . .
I1 I 0.63765(4) 0.13971(9) 0.07852(2) 0.0245(2) Uani 1 1 d . . . . .
I2 I 0.59133(4) -0.36295(9) 0.27589(2) 0.0226(2) Uani 1 1 d . . . . .
C3 C 0.1807(6) -0.3738(14) 0.1468(3) 0.0260(15) Uani 1 1 d . . . . .
H3A H 0.1081 -0.3212 0.1639 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2846(6) -0.2730(15) 0.1707(3) 0.0243(14) Uani 1 1 d . . . . .
H2A H 0.2954 -0.1386 0.2077 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3191(6) -0.5795(14) 0.0854(3) 0.0229(14) Uani 1 1 d . . . . .
H1A H 0.3568 -0.6979 0.0523 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1174(6) -0.7385(16) 0.0507(3) 0.0269(14) Uani 1 1 d . . . . .
H4A H 0.0601 -0.8340 0.0803 0.032 Uiso 1 1 calc R U . . .
H4B H 0.1564 -0.9067 0.0264 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0560(6) -0.5259(15) -0.0004(3) 0.0240(13) Uani 1 1 d . . . . .
H5A H 0.1002 -0.4278 -0.0338 0.029 Uiso 1 1 calc R U . . .
N1 N 0.3734(5) -0.4023(11) 0.1311(3) 0.0227(12) Uani 1 1 d . . . . .
N2 N 0.2023(4) -0.5686(11) 0.0924(2) 0.0197(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 I1 2.5827(11) . ?
Cu1 I2 2.6763(9) 1_565 ?
Cu1 I2 2.6790(9) . ?
Cu1 I2 2.7070(12) 2_655 ?
Cu1 Cu2 2.8921(14) . ?
Cu1 Cu2 2.9664(14) 1_565 ?
Cu2 N1 1.987(6) . ?
Cu2 I1 2.6244(9) . ?
Cu2 I1 2.6909(9) 1_545 ?
Cu2 I2 2.7334(11) . ?
Cu2 Cu1 2.9664(14) 1_545 ?
I1 Cu2 2.6909(9) 1_565 ?
I2 Cu1 2.6764(9) 1_545 ?
I2 Cu1 2.7070(12) 2_645 ?
C3 C2 1.350(10) . ?
C3 N2 1.372(8) . ?
C3 H3A 0.9300 . ?
C2 N1 1.401(8) . ?
C2 H2A 0.9300 . ?
C1 N1 1.322(9) . ?
C1 N2 1.353(8) . ?
C1 H1A 0.9300 . ?
C4 N2 1.460(8) . ?
C4 C5 1.517(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.309(13) 3_545 ?
C5 H5A 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
I1 Cu1 I2 115.18(4) . 1_565 ?
I1 Cu1 I2 115.53(4) . . ?
I2 Cu1 I2 104.74(3) 1_565 . ?
I1 Cu1 I2 105.47(3) . 2_655 ?
I2 Cu1 I2 107.82(4) 1_565 2_655 ?
I2 Cu1 I2 107.74(4) . 2_655 ?
I1 Cu1 Cu2 56.95(3) . . ?
I2 Cu1 Cu2 127.77(5) 1_565 . ?
I2 Cu1 Cu2 58.62(3) . . ?
I2 Cu1 Cu2 124.28(4) 2_655 . ?
I1 Cu1 Cu2 57.52(3) . 1_565 ?
I2 Cu1 Cu2 57.67(3) 1_565 1_565 ?
I2 Cu1 Cu2 128.67(5) . 1_565 ?
I2 Cu1 Cu2 123.37(4) 2_655 1_565 ?
Cu2 Cu1 Cu2 92.75(5) . 1_565 ?
N1 Cu2 I1 117.43(15) . . ?
N1 Cu2 I1 105.96(15) . 1_545 ?
I1 Cu2 I1 105.86(3) . 1_545 ?
N1 Cu2 I2 105.13(16) . . ?
I1 Cu2 I2 112.33(3) . . ?
I1 Cu2 I2 109.88(3) 1_545 . ?
N1 Cu2 Cu1 128.70(15) . . ?
I1 Cu2 Cu1 55.58(3) . . ?
I1 Cu2 Cu1 125.19(4) 1_545 . ?
I2 Cu2 Cu1 56.79(3) . . ?
N1 Cu2 Cu1 116.83(15) . 1_545 ?
I1 Cu2 Cu1 125.55(4) . 1_545 ?
I1 Cu2 Cu1 54.06(2) 1_545 1_545 ?
I2 Cu2 Cu1 55.83(3) . 1_545 ?
Cu1 Cu2 Cu1 92.75(5) . 1_545 ?
Cu1 I1 Cu2 67.47(3) . . ?
Cu1 I1 Cu2 68.42(3) . 1_565 ?
Cu2 I1 Cu2 105.86(3) . 1_565 ?
Cu1 I2 Cu1 104.74(3) 1_545 . ?
Cu1 I2 Cu1 72.24(3) 1_545 2_645 ?
Cu1 I2 Cu1 72.20(3) . 2_645 ?
Cu1 I2 Cu2 66.50(3) 1_545 . ?
Cu1 I2 Cu2 64.59(3) . . ?
Cu1 I2 Cu2 107.30(3) 2_645 . ?
C2 C3 N2 107.1(5) . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
C3 C2 N1 109.4(6) . . ?
C3 C2 H2A 125.3 . . ?
N1 C2 H2A 125.3 . . ?
N1 C1 N2 112.2(5) . . ?
N1 C1 H1A 123.9 . . ?
N2 C1 H1A 123.9 . . ?
N2 C4 C5 112.4(5) . . ?
N2 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C5 C4 123.1(7) 3_545 . ?
C5 C5 H5A 118.5 3_545 . ?
C4 C5 H5A 118.5 . . ?
C1 N1 C2 104.7(6) . . ?
C1 N1 Cu2 125.4(4) . . ?
C2 N1 Cu2 129.9(5) . . ?
C1 N2 C3 106.6(5) . . ?
C1 N2 C4 126.0(5) . . ?
C3 N2 C4 127.4(5) . . ?

_refine_diff_density_max         1.454
_refine_diff_density_min         -1.589
_refine_diff_density_rms         0.261

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_220k
_database_code_depnum_ccdc_archive 'CCDC 1975153'
loop_
_audit_author_name
_audit_author_address
Wu
;Changzhou University
China
;
_audit_update_record             
;
2020-05-09 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Cu2 I2 N2'
_chemical_formula_weight         475.00

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'
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'

_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                   11.5218(4)
_cell_length_b                   4.2497(2)
_cell_length_c                   19.6222(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.458(4)
_cell_angle_gamma                90
_cell_volume                     960.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    3962
_cell_measurement_theta_min      2.0640
_cell_measurement_theta_max      30.1790

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.284
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    10.792
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.02801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6063
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             1673
_reflns_number_gt                1426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+1.2207P] 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         1673
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1513
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.67545(13) 0.1358(2) 0.20900(7) 0.0457(4) Uani 1 1 d . . . . .
Cu2 Cu 0.54376(10) -0.3514(2) 0.13826(7) 0.0388(4) Uani 1 1 d . . . . .
I1 I 0.63782(5) 0.13821(10) 0.07890(3) 0.0282(3) Uani 1 1 d . . . . .
I2 I 0.59094(5) -0.36448(11) 0.27551(3) 0.0260(3) Uani 1 1 d . . . . .
C3 C 0.1795(7) -0.3761(16) 0.1464(4) 0.0273(19) Uani 1 1 d . . . . .
H3A H 0.1069 -0.3259 0.1637 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2844(7) -0.2729(19) 0.1697(4) 0.0315(18) Uani 1 1 d . . . . .
H2A H 0.2953 -0.1338 0.2058 0.038 Uiso 1 1 calc R U . . .
C1 C 0.3178(7) -0.5785(17) 0.0847(4) 0.0266(17) Uani 1 1 d . . . . .
H1A H 0.3545 -0.6925 0.0507 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1170(6) -0.7387(18) 0.0507(4) 0.0277(17) Uani 1 1 d . . . . .
H4A H 0.0594 -0.8346 0.0799 0.033 Uiso 1 1 calc R U . . .
H4B H 0.1563 -0.9057 0.0263 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0571(7) -0.5237(18) 0.0001(4) 0.0283(17) Uani 1 1 d . . . . .
H5A H 0.1018 -0.4201 -0.0321 0.034 Uiso 1 1 calc R U . . .
N1 N 0.3730(6) -0.4067(14) 0.1315(4) 0.0266(15) Uani 1 1 d . . . . .
N2 N 0.2020(5) -0.5661(14) 0.0930(3) 0.0236(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 I1 2.5859(15) . ?
Cu1 I2 2.6798(11) 1_565 ?
Cu1 I2 2.6818(11) . ?
Cu1 I2 2.7063(17) 2_655 ?
Cu1 Cu2 2.9125(19) . ?
Cu1 Cu2 2.9906(19) 1_565 ?
Cu2 N1 1.984(7) . ?
Cu2 I1 2.6231(11) . ?
Cu2 I1 2.6936(11) 1_545 ?
Cu2 I2 2.7437(14) . ?
Cu2 Cu1 2.9906(19) 1_545 ?
I1 Cu2 2.6936(11) 1_565 ?
I2 Cu1 2.6798(11) 1_545 ?
I2 Cu1 2.7063(17) 2_645 ?
C3 N2 1.350(10) . ?
C3 C2 1.362(12) . ?
C3 H3A 0.9300 . ?
C2 N1 1.393(10) . ?
C2 H2A 0.9300 . ?
C1 N1 1.331(11) . ?
C1 N2 1.345(9) . ?
C1 H1A 0.9300 . ?
C4 N2 1.474(10) . ?
C4 C5 1.512(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.330(16) 3_545 ?
C5 H5A 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
I1 Cu1 I2 114.77(5) . 1_565 ?
I1 Cu1 I2 115.14(5) . . ?
I2 Cu1 I2 104.86(4) 1_565 . ?
I1 Cu1 I2 105.65(5) . 2_655 ?
I2 Cu1 I2 108.10(5) 1_565 2_655 ?
I2 Cu1 I2 108.04(5) . 2_655 ?
I1 Cu1 Cu2 56.61(4) . . ?
I2 Cu1 Cu2 127.27(6) 1_565 . ?
I2 Cu1 Cu2 58.57(3) . . ?
I2 Cu1 Cu2 124.55(5) 2_655 . ?
I1 Cu1 Cu2 57.22(4) . 1_565 ?
I2 Cu1 Cu2 57.56(3) 1_565 1_565 ?
I2 Cu1 Cu2 128.22(6) . 1_565 ?
I2 Cu1 Cu2 123.57(5) 2_655 1_565 ?
Cu2 Cu1 Cu2 92.08(7) . 1_565 ?
N1 Cu2 I1 118.5(2) . . ?
N1 Cu2 I1 106.14(19) . 1_545 ?
I1 Cu2 I1 106.12(4) . 1_545 ?
N1 Cu2 I2 104.6(2) . . ?
I1 Cu2 I2 111.87(4) . . ?
I1 Cu2 I2 109.32(4) 1_545 . ?
N1 Cu2 Cu1 128.92(19) . . ?
I1 Cu2 Cu1 55.40(3) . . ?
I1 Cu2 Cu1 124.66(6) 1_545 . ?
I2 Cu2 Cu1 56.51(4) . . ?
N1 Cu2 Cu1 116.34(19) . 1_545 ?
I1 Cu2 Cu1 125.04(6) . 1_545 ?
I1 Cu2 Cu1 53.81(3) 1_545 1_545 ?
I2 Cu2 Cu1 55.52(4) . 1_545 ?
Cu1 Cu2 Cu1 92.08(7) . 1_545 ?
Cu1 I1 Cu2 67.99(4) . . ?
Cu1 I1 Cu2 68.97(4) . 1_565 ?
Cu2 I1 Cu2 106.12(4) . 1_565 ?
Cu1 I2 Cu1 104.86(4) 1_545 . ?
Cu1 I2 Cu1 71.95(4) 1_545 2_645 ?
Cu1 I2 Cu1 71.92(4) . 2_645 ?
Cu1 I2 Cu2 66.92(4) 1_545 . ?
Cu1 I2 Cu2 64.92(4) . . ?
Cu1 I2 Cu2 107.41(4) 2_645 . ?
N2 C3 C2 106.1(6) . . ?
N2 C3 H3A 126.9 . . ?
C2 C3 H3A 126.9 . . ?
C3 C2 N1 109.9(7) . . ?
C3 C2 H2A 125.1 . . ?
N1 C2 H2A 125.1 . . ?
N1 C1 N2 111.4(6) . . ?
N1 C1 H1A 124.3 . . ?
N2 C1 H1A 124.3 . . ?
N2 C4 C5 111.5(6) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C5 C5 C4 122.7(9) 3_545 . ?
C5 C5 H5A 118.6 3_545 . ?
C4 C5 H5A 118.6 . . ?
C1 N1 C2 104.3(7) . . ?
C1 N1 Cu2 125.4(5) . . ?
C2 N1 Cu2 130.3(6) . . ?
C1 N2 C3 108.3(7) . . ?
C1 N2 C4 124.6(6) . . ?
C3 N2 C4 127.1(6) . . ?

_refine_diff_density_max         2.645
_refine_diff_density_min         -2.453
_refine_diff_density_rms         0.396

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_260K
_database_code_depnum_ccdc_archive 'CCDC 1975154'
loop_
_audit_author_name
_audit_author_address
Wu
;Changzhou University
China
;
_audit_update_record             
;
2020-05-09 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Cu2 I2 N2'
_chemical_formula_weight         475.00

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'
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'

_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                   11.5363(6)
_cell_length_b                   4.2584(2)
_cell_length_c                   19.6624(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.490(5)
_cell_angle_gamma                90
_cell_volume                     965.90(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    3541
_cell_measurement_theta_min      2.0580
_cell_measurement_theta_max      30.1610

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.266
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    10.734
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.05500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4734
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             1635
_reflns_number_gt                1290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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         1635
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0828
_refine_ls_wR_factor_ref         0.2506
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
I1 I 0.13803(7) 0.36349(15) 0.07930(4) 0.0364(5) Uani 1 1 d . . . . .
I2 I 0.09064(7) 0.86641(15) 0.27511(4) 0.0334(5) Uani 1 1 d . . . . .
Cu1 Cu 0.04311(15) 0.8529(3) 0.13753(11) 0.0493(6) Uani 1 1 d . . . . .
Cu2 Cu 0.17621(19) 0.3663(4) 0.20925(11) 0.0576(7) Uani 1 1 d . . . . .
C1 C -0.1822(11) 1.079(3) 0.0846(6) 0.038(3) Uani 1 1 d . . . . .
H1A H -0.1455 1.1957 0.0510 0.046 Uiso 1 1 calc R U . . .
C2 C -0.2162(9) 0.780(3) 0.1689(6) 0.037(2) Uani 1 1 d . . . . .
H2A H -0.2041 0.6467 0.2057 0.044 Uiso 1 1 calc R U . . .
C3 C -0.3204(11) 0.876(2) 0.1470(8) 0.042(3) Uani 1 1 d . . . . .
H3A H -0.3924 0.8229 0.1646 0.051 Uiso 1 1 calc R U . . .
C4 C -0.3853(9) 1.234(3) 0.0507(6) 0.038(3) Uani 1 1 d . . . . .
H4A H -0.3476 1.4048 0.0267 0.046 Uiso 1 1 calc R U . . .
H4B H -0.4434 1.3249 0.0801 0.046 Uiso 1 1 calc R U . . .
C5 C -0.4439(10) 1.023(3) -0.0002(7) 0.042(3) Uani 1 1 d . . . . .
H5A H -0.3993 0.9232 -0.0329 0.051 Uiso 1 1 calc R U . . .
N1 N -0.1282(9) 0.907(2) 0.1295(6) 0.035(2) Uani 1 1 d . . . . .
N2 N -0.2979(7) 1.068(2) 0.0930(5) 0.032(2) 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 Cu2 2.589(2) . ?
I1 Cu1 2.6220(16) . ?
I1 Cu1 2.6941(16) 1_545 ?
I2 Cu2 2.6843(17) 1_565 ?
I2 Cu2 2.6848(17) . ?
I2 Cu2 2.705(3) 2 ?
I2 Cu1 2.756(2) . ?
Cu1 N1 1.994(10) . ?
Cu1 I1 2.6940(16) 1_565 ?
Cu1 Cu2 2.933(3) . ?
Cu1 Cu2 3.015(3) 1_565 ?
Cu2 I2 2.6843(17) 1_545 ?
Cu2 I2 2.705(3) 2_545 ?
Cu2 Cu1 3.015(3) 1_545 ?
C1 N1 1.304(16) . ?
C1 N2 1.348(14) . ?
C1 H1A 0.9300 . ?
C2 C3 1.337(19) . ?
C2 N1 1.390(14) . ?
C2 H2A 0.9300 . ?
C3 N2 1.367(15) . ?
C3 H3A 0.9300 . ?
C4 N2 1.482(14) . ?
C4 C5 1.500(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.31(2) 3_475 ?
C5 H5A 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
Cu2 I1 Cu1 68.50(6) . . ?
Cu2 I1 Cu1 69.56(6) . 1_545 ?
Cu1 I1 Cu1 106.45(6) . 1_545 ?
Cu2 I2 Cu2 104.96(7) 1_565 . ?
Cu2 I2 Cu2 71.67(7) 1_565 2 ?
Cu2 I2 Cu2 71.66(6) . 2 ?
Cu2 I2 Cu1 67.29(6) 1_565 . ?
Cu2 I2 Cu1 65.23(6) . . ?
Cu2 I2 Cu1 107.52(6) 2 . ?
N1 Cu1 I1 118.3(3) . . ?
N1 Cu1 I1 106.2(3) . 1_565 ?
I1 Cu1 I1 106.45(6) . 1_565 ?
N1 Cu1 I2 105.3(3) . . ?
I1 Cu1 I2 111.39(6) . . ?
I1 Cu1 I2 108.79(6) 1_565 . ?
N1 Cu1 Cu2 129.3(3) . . ?
I1 Cu1 Cu2 55.21(5) . . ?
I1 Cu1 Cu2 124.15(8) 1_565 . ?
I2 Cu1 Cu2 56.21(6) . . ?
N1 Cu1 Cu2 117.0(3) . 1_565 ?
I1 Cu1 Cu2 124.59(8) . 1_565 ?
I1 Cu1 Cu2 53.58(5) 1_565 1_565 ?
I2 Cu1 Cu2 55.22(6) . 1_565 ?
Cu2 Cu1 Cu2 91.43(10) . 1_565 ?
I1 Cu2 I2 114.34(7) . 1_545 ?
I1 Cu2 I2 114.81(7) . . ?
I2 Cu2 I2 104.96(7) 1_545 . ?
I1 Cu2 I2 105.84(7) . 2_545 ?
I2 Cu2 I2 108.34(7) 1_545 2_545 ?
I2 Cu2 I2 108.33(7) . 2_545 ?
I1 Cu2 Cu1 56.28(6) . . ?
I2 Cu2 Cu1 126.80(9) 1_545 . ?
I2 Cu2 Cu1 58.56(5) . . ?
I2 Cu2 Cu1 124.79(7) 2_545 . ?
I1 Cu2 Cu1 56.86(6) . 1_545 ?
I2 Cu2 Cu1 57.49(5) 1_545 1_545 ?
I2 Cu2 Cu1 127.80(9) . 1_545 ?
I2 Cu2 Cu1 123.73(7) 2_545 1_545 ?
Cu1 Cu2 Cu1 91.43(10) . 1_545 ?
N1 C1 N2 111.3(10) . . ?
N1 C1 H1A 124.3 . . ?
N2 C1 H1A 124.3 . . ?
C3 C2 N1 111.2(11) . . ?
C3 C2 H2A 124.4 . . ?
N1 C2 H2A 124.4 . . ?
C2 C3 N2 104.8(9) . . ?
C2 C3 H3A 127.6 . . ?
N2 C3 H3A 127.6 . . ?
N2 C4 C5 112.8(9) . . ?
N2 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C5 C4 121.8(14) 3_475 . ?
C5 C5 H5A 119.1 3_475 . ?
C4 C5 H5A 119.1 . . ?
C1 N1 C2 104.4(10) . . ?
C1 N1 Cu1 125.8(8) . . ?
C2 N1 Cu1 129.7(9) . . ?
C1 N2 C3 108.2(10) . . ?
C1 N2 C4 125.6(9) . . ?
C3 N2 C4 126.2(9) . . ?

_refine_diff_density_max         2.083
_refine_diff_density_min         -4.778
_refine_diff_density_rms         0.586

_shelxl_version_number           2014/6

