# 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 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_20200328ghyz0315_4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1999513'
loop_
_audit_author_name
_audit_author_address
'Wei Liu'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 Cu I N2 O'
_chemical_formula_weight         300.56

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   4.1928(2)
_cell_length_b                   8.2514(4)
_cell_length_c                   11.4846(6)
_cell_angle_alpha                84.065(2)
_cell_angle_beta                 89.980(2)
_cell_angle_gamma                76.690(2)
_cell_volume                     384.47(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4059
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.26

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.596
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    6.785
_shelx_estimated_absorpt_T_min   0.496
_shelx_estimated_absorpt_T_max   0.580
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.1578
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6203
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         28.257
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1901
_reflns_number_gt                1723
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0293P)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         1901
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.3096(9) 0.2843(5) 0.4494(3) 0.0348(8) Uani 1 1 d . . . . .
H1A H 0.519037 0.279839 0.410489 0.052 Uiso 1 1 calc R U . . .
H1B H 0.131071 0.353252 0.398548 0.052 Uiso 1 1 calc R U . . .
H1C H 0.274776 0.170700 0.465137 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5470(7) 0.2755(4) 0.6383(3) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.9587(8) 0.0616(4) 0.7069(3) 0.0311(7) Uani 1 1 d . . . . .
H3 H 1.105036 -0.042631 0.697685 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5655(7) 0.3531(4) 0.7402(3) 0.0249(6) Uani 1 1 d . . . . .
H4 H 0.418790 0.457386 0.748967 0.030 Uiso 1 1 calc R U . . .
C5 C 0.9820(8) 0.1334(4) 0.8084(3) 0.0276(7) Uani 1 1 d . . . . .
H5 H 1.138164 0.077177 0.867697 0.033 Uiso 1 1 calc R U . . .
Cu1 Cu 0.78912(9) 0.39526(5) 0.97517(4) 0.02482(11) Uani 1 1 d . . . . .
I1 I 0.66890(4) 0.71881(2) 0.90085(2) 0.02183(8) Uani 1 1 d . . . . .
N1 N 0.7417(6) 0.1303(3) 0.6205(3) 0.0275(6) Uani 1 1 d . . . . .
N2 N 0.7846(6) 0.2833(3) 0.8245(2) 0.0240(5) Uani 1 1 d . . . . .
O1 O 0.3153(6) 0.3567(3) 0.5585(2) 0.0307(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
C1 O1 1.446(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.320(4) . ?
C2 O1 1.344(4) . ?
C2 C4 1.401(4) . ?
C3 N1 1.334(5) . ?
C3 C5 1.375(5) . ?
C3 H3 0.9500 . ?
C4 N2 1.325(4) . ?
C4 H4 0.9500 . ?
C5 N2 1.351(4) . ?
C5 H5 0.9500 . ?
Cu1 N2 2.046(3) . ?
Cu1 I1 2.6111(4) 2_767 ?
Cu1 I1 2.6494(5) . ?
Cu1 I1 2.6748(4) 2_667 ?
Cu1 Cu1 2.7321(7) 2_667 ?
Cu1 Cu1 2.8376(8) 2_767 ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 O1 121.0(3) . . ?
N1 C2 C4 122.8(3) . . ?
O1 C2 C4 116.1(3) . . ?
N1 C3 C5 123.5(3) . . ?
N1 C3 H3 118.2 . . ?
C5 C3 H3 118.2 . . ?
N2 C4 C2 120.9(3) . . ?
N2 C4 H4 119.5 . . ?
C2 C4 H4 119.5 . . ?
N2 C5 C3 120.5(3) . . ?
N2 C5 H5 119.7 . . ?
C3 C5 H5 119.7 . . ?
N2 Cu1 I1 112.97(7) . 2_767 ?
N2 Cu1 I1 103.67(8) . . ?
I1 Cu1 I1 114.717(15) 2_767 . ?
N2 Cu1 I1 101.71(8) . 2_667 ?
I1 Cu1 I1 104.967(16) 2_767 2_667 ?
I1 Cu1 I1 118.256(14) . 2_667 ?
N2 Cu1 Cu1 115.34(7) . 2_667 ?
I1 Cu1 Cu1 131.17(2) 2_767 2_667 ?
I1 Cu1 Cu1 59.585(16) . 2_667 ?
I1 Cu1 Cu1 58.671(15) 2_667 2_667 ?
N2 Cu1 Cu1 125.44(8) . 2_767 ?
I1 Cu1 Cu1 58.011(14) 2_767 2_767 ?
I1 Cu1 Cu1 56.706(15) . 2_767 ?
I1 Cu1 Cu1 132.82(2) 2_667 2_767 ?
Cu1 Cu1 Cu1 97.65(2) 2_667 2_767 ?
Cu1 I1 Cu1 65.283(15) 2_767 . ?
Cu1 I1 Cu1 104.967(16) 2_767 2_667 ?
Cu1 I1 Cu1 61.744(14) . 2_667 ?
C2 N1 C3 115.2(3) . . ?
C4 N2 C5 116.9(3) . . ?
C4 N2 Cu1 119.7(2) . . ?
C5 N2 Cu1 123.3(2) . . ?
C2 O1 C1 116.7(3) . . ?

_refine_diff_density_max         0.850
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.160

####################################################################### 
# 
# 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_20200328ghyz0313_9_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1999522'
loop_
_audit_author_name
_audit_author_address
'Wei Liu'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Cu2 I2 N2'
_chemical_formula_weight         489.02

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'

_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                   4.2966(2)
_cell_length_b                   17.8851(9)
_cell_length_c                   13.0424(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.310(2)
_cell_angle_gamma                90
_cell_volume                     1001.43(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6046
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.27

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.244
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    10.358
_shelx_estimated_absorpt_T_min   0.370
_shelx_estimated_absorpt_T_max   0.491
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.1706
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9652
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.934
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2480
_reflns_number_gt                2253
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0125P)²+2.9586P] 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         2480
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.020
_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 1.10291(5) 0.40306(2) 0.59724(2) 0.01659(7) Uani 1 1 d . . . . .
I2 I 0.98332(5) 0.86497(2) 0.62461(2) 0.01708(7) Uani 1 1 d . . . . .
Cu1 Cu 0.63318(11) 0.44333(3) 0.70617(4) 0.02093(12) Uani 1 1 d . . . . .
Cu2 Cu 0.50499(11) 0.82584(3) 0.73393(4) 0.02021(11) Uani 1 1 d . . . . .
N1 N 0.6126(7) 0.55701(19) 0.7226(3) 0.0170(7) Uani 1 1 d . . . . .
N2 N 0.5413(7) 0.71127(19) 0.7376(3) 0.0171(7) Uani 1 1 d . . . . .
C5 C 0.4349(9) 0.5955(2) 0.6542(3) 0.0196(8) Uani 1 1 d . . . . .
H5 H 0.331514 0.569512 0.599142 0.024 Uiso 1 1 calc R U . . .
C2 C 0.7608(8) 0.5955(2) 0.7977(3) 0.0154(7) Uani 1 1 d . . . . .
C4 C 0.3986(9) 0.6719(2) 0.6619(3) 0.0206(8) Uani 1 1 d . . . . .
H4 H 0.269227 0.697280 0.612426 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7260(8) 0.6740(2) 0.8052(3) 0.0159(7) Uani 1 1 d . . . . .
C1 C 0.9609(9) 0.5530(2) 0.8739(3) 0.0219(8) Uani 1 1 d . . . . .
H1A H 0.843926 0.543503 0.935571 0.033 Uiso 1 1 calc R U . . .
H1B H 1.147628 0.582271 0.892317 0.033 Uiso 1 1 calc R U . . .
H1C H 1.022194 0.505244 0.843811 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8875(9) 0.7178(2) 0.8883(3) 0.0199(8) Uani 1 1 d . . . . .
H6A H 1.029141 0.753829 0.858074 0.030 Uiso 1 1 calc R U . . .
H6B H 1.006737 0.683834 0.933859 0.030 Uiso 1 1 calc R U . . .
H6C H 0.733067 0.744559 0.927603 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
I1 Cu1 2.6156(6) . ?
I1 Cu2 2.6557(6) 2_646 ?
I1 Cu1 2.7326(6) 1_655 ?
I2 Cu2 2.6426(6) . ?
I2 Cu1 2.6786(6) 2_656 ?
I2 Cu2 2.6999(6) 1_655 ?
Cu1 N1 2.047(4) . ?
Cu1 Cu2 2.7101(7) 2_646 ?
Cu2 N2 2.055(3) . ?
N1 C2 1.338(5) . ?
N1 C5 1.340(5) . ?
N2 C4 1.340(5) . ?
N2 C3 1.340(5) . ?
C5 C4 1.381(6) . ?
C5 H5 0.9500 . ?
C2 C3 1.415(5) . ?
C2 C1 1.496(5) . ?
C4 H4 0.9500 . ?
C3 C6 1.486(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
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
Cu1 I1 Cu2 61.872(17) . 2_646 ?
Cu1 I1 Cu1 106.89(2) . 1_655 ?
Cu2 I1 Cu1 82.864(18) 2_646 1_655 ?
Cu2 I2 Cu1 61.232(17) . 2_656 ?
Cu2 I2 Cu2 107.07(2) . 1_655 ?
Cu1 I2 Cu2 83.061(18) 2_656 1_655 ?
N1 Cu1 I1 111.58(9) . . ?
N1 Cu1 I2 115.04(10) . 2_646 ?
I1 Cu1 I2 118.52(2) . 2_646 ?
N1 Cu1 Cu2 140.07(10) . 2_646 ?
I1 Cu1 Cu2 59.791(17) . 2_646 ?
I2 Cu1 Cu2 58.729(17) 2_646 2_646 ?
N1 Cu1 I1 106.11(9) . 1_455 ?
I1 Cu1 I1 106.89(2) . 1_455 ?
I2 Cu1 I1 96.368(18) 2_646 1_455 ?
Cu2 Cu1 I1 113.71(2) 2_646 1_455 ?
N2 Cu2 I2 102.51(9) . . ?
N2 Cu2 I1 120.98(10) . 2_656 ?
I2 Cu2 I1 118.37(2) . 2_656 ?
N2 Cu2 I2 109.35(10) . 1_455 ?
I2 Cu2 I2 107.07(2) . 1_455 ?
I1 Cu2 I2 97.706(18) 2_656 1_455 ?
N2 Cu2 Cu1 136.40(10) . 2_656 ?
I2 Cu2 Cu1 60.039(17) . 2_656 ?
I1 Cu2 Cu1 58.336(17) 2_656 2_656 ?
I2 Cu2 Cu1 113.93(2) 1_455 2_656 ?
C2 N1 C5 117.7(4) . . ?
C2 N1 Cu1 124.5(3) . . ?
C5 N1 Cu1 117.8(3) . . ?
C4 N2 C3 117.7(4) . . ?
C4 N2 Cu2 118.3(3) . . ?
C3 N2 Cu2 123.6(3) . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N1 C2 C3 120.9(4) . . ?
N1 C2 C1 117.9(4) . . ?
C3 C2 C1 121.2(4) . . ?
N2 C4 C5 121.6(4) . . ?
N2 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
N2 C3 C2 120.6(4) . . ?
N2 C3 C6 117.7(4) . . ?
C2 C3 C6 121.7(4) . . ?
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 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.177

####################################################################### 
# 
# 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_20200328gfdz2156_0315_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1999520'
loop_
_audit_author_name
_audit_author_address
'Wei Liu'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Cu I N2'
_chemical_formula_weight         298.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.7490(6)
_cell_length_b                   7.7769(5)
_cell_length_c                   8.1453(5)
_cell_angle_alpha                72.597(2)
_cell_angle_beta                 66.733(2)
_cell_angle_gamma                70.721(2)
_cell_volume                     417.52(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2875
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.24

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.375
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.238
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.635
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.1656
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4137
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         28.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2053
_reflns_number_gt                1895
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0248P)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         2053
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.017
_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 0.6241(7) 0.2918(6) 0.2083(6) 0.0243(9) Uani 1 1 d . . . . .
H1A H 0.552053 0.325394 0.123280 0.036 Uiso 1 1 calc R U . . .
H1B H 0.762584 0.249471 0.144062 0.036 Uiso 1 1 calc R U . . .
H1C H 0.602024 0.400344 0.257996 0.036 Uiso 1 1 calc R U . . .
C2 C 0.5561(6) 0.1390(5) 0.3607(5) 0.0175(7) Uani 1 1 d . . . . .
C3 C 0.3122(6) 0.0100(5) 0.5755(5) 0.0162(7) Uani 1 1 d . . . . .
H3 H 0.178193 0.013302 0.631919 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2989(7) 0.1696(5) 0.0132(6) 0.0243(9) Uani 1 1 d . . . . .
H4A H 0.422142 0.201536 -0.019384 0.036 Uiso 1 1 calc R U . . .
H4B H 0.309063 0.100303 -0.074152 0.036 Uiso 1 1 calc R U . . .
H4C H 0.268863 0.092924 0.135956 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1429(6) 0.3419(5) 0.0090(5) 0.0155(7) Uani 1 1 d . . . . .
C6 C -0.0640(6) 0.5944(5) 0.1318(5) 0.0158(7) Uani 1 1 d . . . . .
H6 H -0.113506 0.664101 0.225491 0.019 Uiso 1 1 calc R U . . .
Cu1 Cu 0.15683(8) 0.36604(6) 0.36942(7) 0.01947(13) Uani 1 1 d . . . . .
I1 I 0.19122(4) 0.69125(3) 0.38802(3) 0.01859(9) Uani 1 1 d . . . . .
N1 N 0.3651(5) 0.1495(4) 0.4380(4) 0.0154(6) Uani 1 1 d . . . . .
N2 N 0.0783(5) 0.4399(4) 0.1416(4) 0.0155(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.498(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.345(5) . ?
C2 C3 1.390(5) 2_656 ?
C3 N1 1.343(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.481(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.346(4) . ?
C5 C6 1.396(5) 2_565 ?
C6 N2 1.343(5) . ?
C6 H6 0.9500 . ?
Cu1 N1 2.027(3) . ?
Cu1 N2 2.041(3) . ?
Cu1 I1 2.6826(5) . ?
Cu1 I1 2.7263(6) 2_566 ?

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
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 . . ?
N1 C2 C3 120.2(4) . 2_656 ?
N1 C2 C1 119.1(3) . . ?
C3 C2 C1 120.7(4) 2_656 . ?
N1 C3 C2 123.2(4) . 2_656 ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 2_656 . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 119.5(3) . 2_565 ?
N2 C5 C4 119.5(3) . . ?
C6 C5 C4 121.0(3) 2_565 . ?
N2 C6 C5 123.4(3) . 2_565 ?
N2 C6 H6 118.3 . . ?
C5 C6 H6 118.3 2_565 . ?
N1 Cu1 N2 129.45(12) . . ?
N1 Cu1 I1 112.08(9) . . ?
N2 Cu1 I1 101.13(8) . . ?
N1 Cu1 I1 107.28(9) . 2_566 ?
N2 Cu1 I1 96.33(10) . 2_566 ?
I1 Cu1 I1 108.464(18) . 2_566 ?
Cu1 I1 Cu1 71.535(19) . 2_566 ?
C3 N1 C2 116.6(3) . . ?
C3 N1 Cu1 119.0(3) . . ?
C2 N1 Cu1 124.3(2) . . ?
C6 N2 C5 117.0(3) . . ?
C6 N2 Cu1 116.1(2) . . ?
C5 N2 Cu1 126.6(3) . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.193

