# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2361461'
loop_
_audit_author_name
_audit_author_address
'Jie Zhang'
;Jining  University
China
;
_audit_update_record             
;
2024-06-09 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_audit_creation_date             2024-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cu2 I4, C9 H22 N2'
_chemical_formula_sum            'C9 H22 Cu2 I4 N2'
_chemical_formula_weight         792.96
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7267(2)
_cell_length_b                   8.4253(3)
_cell_length_c                   16.8186(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.1730(10)
_cell_angle_gamma                90
_cell_volume                     947.66(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6260
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.287
_shelx_estimated_absorpt_T_min   0.249
_exptl_absorpt_coefficient_mu    8.745
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.3418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.779
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7708
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3086
_reflns_number_total             3189
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Flack x determined using 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0040(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.131
_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)+(0.0149P)²+0.5450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0486
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Restrained distances
 Cu1-I1 \\sim Cu1A-I1
 with sigma of 0.02
 Cu1-I2 \\sim Cu1A-I2
 with sigma of 0.02
3. Rigid bond restraints
 Cu1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(Cu1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(Cu1A)=1-FVAR(1)
 Sof(Cu1)=FVAR(1)
 Sof(Cu2A)=1-FVAR(2)
 Sof(Cu2)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2)
6.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C1(H1D,H1E), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
6.c Me refined with riding coordinates:
 N1(H1A,H1B,H1C)
;
_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 -1.0014(13) -0.5652(14) -0.3030(5) 0.035(3) Uani 0.290(18) 1 d D U P A 1
Cu2 Cu -0.5227(12) -0.5642(10) -0.2996(4) 0.0463(15) Uani 0.62(6) 1 d . . P A 1
I1 I -0.78730(7) -0.54161(6) -0.43321(4) 0.03561(16) Uani 1 1 d D . . . .
I2 I -0.73408(7) -0.60796(6) -0.18329(3) 0.03713(16) Uani 1 1 d D . . . .
I3 I -0.27714(7) -0.80199(6) -0.32783(4) 0.04706(18) Uani 1 1 d . . . . .
I4 I -0.25404(7) -0.31961(6) -0.29250(4) 0.03818(16) Uani 1 1 d . . . . .
N1 N 0.3031(10) 0.0432(9) -0.5022(4) 0.0395(17) Uani 1 1 d . . . . .
H1A H 0.376018 0.009533 -0.540024 0.059 Uiso 1 1 calc R U . . .
H1B H 0.175062 0.047967 -0.521993 0.059 Uiso 1 1 calc R U . . .
H1C H 0.344546 0.139206 -0.485781 0.059 Uiso 1 1 calc R U . . .
N2 N 0.1408(9) -0.0331(8) -0.2282(4) 0.0311(15) Uani 1 1 d . . . . .
H2A H 0.012166 -0.032262 -0.247343 0.037 Uiso 1 1 calc R U . . .
H2B H 0.177847 0.067313 -0.219356 0.037 Uiso 1 1 calc R U . . .
C1 C 0.3722(12) -0.1075(12) -0.1088(5) 0.046(2) Uani 1 1 d . . . . .
H1D H 0.411129 0.002833 -0.101667 0.055 Uiso 1 1 calc R U . . .
H1E H 0.463387 -0.158024 -0.141878 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1595(11) -0.1175(11) -0.1498(5) 0.0331(17) Uani 1 1 d . . . . .
H2 H 0.125826 -0.229543 -0.159427 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0107(13) -0.0469(13) -0.0982(6) 0.048(2) Uani 1 1 d . . . . .
H3A H -0.123708 -0.059404 -0.124737 0.058 Uiso 1 1 calc R U . . .
H3B H 0.036742 0.065664 -0.090950 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0264(16) -0.1294(16) -0.0161(6) 0.068(3) Uani 1 1 d . . . . .
H4A H -0.063848 -0.078374 0.017268 0.081 Uiso 1 1 calc R U . . .
H4B H -0.013981 -0.239481 -0.023036 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2377(15) -0.1219(16) 0.0252(6) 0.068(3) Uani 1 1 d . . . . .
H5A H 0.272527 -0.012397 0.037774 0.082 Uiso 1 1 calc R U . . .
H5B H 0.245049 -0.180825 0.074956 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3851(16) -0.1902(14) -0.0271(6) 0.064(3) Uani 1 1 d . . . . .
H6A H 0.358719 -0.302667 -0.034901 0.077 Uiso 1 1 calc R U . . .
H6B H 0.519420 -0.178764 -0.000326 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2571(10) -0.0982(10) -0.2913(5) 0.0336(18) Uani 1 1 d . . . . .
H7A H 0.229185 -0.210591 -0.298196 0.040 Uiso 1 1 calc R U . . .
H7B H 0.398968 -0.085761 -0.274983 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2029(11) -0.0136(10) -0.3688(6) 0.036(2) Uani 1 1 d . . . . .
H8A H 0.222708 0.099499 -0.360563 0.043 Uiso 1 1 calc R U . . .
H8B H 0.062387 -0.031109 -0.386080 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3258(11) -0.0688(9) -0.4337(5) 0.0333(19) Uani 1 1 d . . . . .
H9A H 0.465525 -0.075204 -0.412504 0.040 Uiso 1 1 calc R U . . .
H9B H 0.282349 -0.173814 -0.451641 0.040 Uiso 1 1 calc R U . . .
Cu1A Cu -1.0362(10) -0.5720(7) -0.2870(5) 0.1003(19) Uani 0.710(18) 1 d D . P A
2
Cu2A Cu -0.477(6) -0.5656(15) -0.285(2) 0.079(5) Uani 0.38(6) 1 d . . P A 2


_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 2.754(6) . ?
Cu1 I2 2.576(10) . ?
Cu1 I3 2.726(11) 1_455 ?
Cu1 I4 2.696(11) 1_455 ?
Cu2 I1 2.719(7) . ?
Cu2 I2 2.566(8) . ?
Cu2 I3 2.671(8) . ?
Cu2 I4 2.735(9) . ?
I1 Cu2A 3.08(5) . ?
I2 Cu1A 2.549(5) . ?
I2 Cu2A 2.587(15) . ?
I3 Cu1A 2.572(6) 1_655 ?
I3 Cu2A 2.548(18) . ?
I4 Cu1A 2.579(6) 1_655 ?
I4 Cu2A 2.57(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C9 1.485(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C2 1.491(10) . ?
N2 C7 1.489(10) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.523(10) . ?
C1 C6 1.535(13) . ?
C2 H2 0.9800 . ?
C2 C3 1.515(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.540(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.514(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.508(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.495(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
Cu1A Cu2A 2.97(4) 1_455 ?

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
I2 Cu1 I1 104.5(3) . . ?
I2 Cu1 I3 115.1(4) . 1_455 ?
I2 Cu1 I4 116.6(4) . 1_455 ?
I3 Cu1 I1 109.7(3) 1_455 . ?
I4 Cu1 I1 112.6(4) 1_455 . ?
I4 Cu1 I3 98.5(3) 1_455 1_455 ?
I1 Cu2 I4 110.7(3) . . ?
I2 Cu2 I1 105.8(3) . . ?
I2 Cu2 I3 115.6(3) . . ?
I2 Cu2 I4 119.5(3) . . ?
I3 Cu2 I1 105.6(3) . . ?
I3 Cu2 I4 98.9(3) . . ?
Cu2 I1 Cu1 71.9(3) . . ?
Cu2 I2 Cu1 77.4(2) . . ?
Cu1A I2 Cu2A 94.2(12) . . ?
Cu2 I3 Cu1 81.2(3) . 1_655 ?
Cu1 I4 Cu2 80.6(3) 1_655 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H2A N2 H2B 107.3 . . ?
C2 N2 H2A 108.1 . . ?
C2 N2 H2B 108.1 . . ?
C7 N2 H2A 108.1 . . ?
C7 N2 H2B 108.1 . . ?
C7 N2 C2 117.0(6) . . ?
H1D C1 H1E 108.2 . . ?
C2 C1 H1D 109.7 . . ?
C2 C1 H1E 109.7 . . ?
C2 C1 C6 109.9(7) . . ?
C6 C1 H1D 109.7 . . ?
C6 C1 H1E 109.7 . . ?
N2 C2 C1 111.1(7) . . ?
N2 C2 H2 108.5 . . ?
N2 C2 C3 108.7(7) . . ?
C1 C2 H2 108.5 . . ?
C3 C2 C1 111.4(7) . . ?
C3 C2 H2 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 C4 110.5(8) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.3(8) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.2(9) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C5 C6 C1 111.8(9) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
N2 C7 C8 110.4(6) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 C9 112.4(7) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N1 C9 C8 110.3(6) . . ?
N1 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
I2 Cu1A I3 121.8(2) . 1_455 ?
I2 Cu1A I4 122.1(2) . 1_455 ?
I2 Cu1A Cu2A 135.9(9) . 1_455 ?
I3 Cu1A I4 105.8(2) 1_455 1_455 ?
I3 Cu1A Cu2A 54.2(3) 1_455 1_455 ?
I4 Cu1A Cu2A 54.6(3) 1_455 1_455 ?
I2 Cu2A I1 95.7(13) . . ?
I2 Cu2A Cu1A 138.2(19) . 1_655 ?
I3 Cu2A I1 98.9(11) . . ?
I3 Cu2A I2 119.3(6) . . ?
I3 Cu2A I4 106.8(10) . . ?
I3 Cu2A Cu1A 55.0(7) . 1_655 ?
I4 Cu2A I1 104.8(11) . . ?
I4 Cu2A I2 125.4(8) . . ?
I4 Cu2A Cu1A 55.0(7) . 1_655 ?
Cu1A Cu2A I1 125.7(8) 1_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C4 -179.4(8) . . . . ?
N2 C7 C8 C9 176.6(6) . . . . ?
C1 C2 C3 C4 -56.6(11) . . . . ?
C2 N2 C7 C8 172.9(7) . . . . ?
C2 C1 C6 C5 -56.2(12) . . . . ?
C2 C3 C4 C5 55.5(13) . . . . ?
C3 C4 C5 C6 -55.2(14) . . . . ?
C4 C5 C6 C1 56.0(13) . . . . ?
C6 C1 C2 N2 178.0(8) . . . . ?
C6 C1 C2 C3 56.6(11) . . . . ?
C7 N2 C2 C1 64.3(9) . . . . ?
C7 N2 C2 C3 -172.7(7) . . . . ?
C7 C8 C9 N1 -166.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
