# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_a446
_database_code_depnum_ccdc_archive 'CCDC 1585190'
loop_
_audit_author_name
_audit_author_address
'Denis Samsonenko' 'Nikolaev Institute of Inorganic Chemistry SB RAS'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H9 Cu2 I2 N O S'
_chemical_formula_weight         536.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7476(4)
_cell_length_b                   9.7854(3)
_cell_length_c                   13.1877(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.066(4)
_cell_angle_gamma                90
_cell_volume                     1230.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5195
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      29.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.895
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    8.614
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            10103
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.425
_diffrn_reflns_theta_max         29.540
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3054
_reflns_number_gt                2697
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0196P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3054
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0486
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.47899(4) 0.62119(5) 0.47367(3) 0.02232(11) Uani 1 1 d . . . . .
Cu2 Cu 0.13147(4) 0.52432(5) 0.49494(3) 0.02020(10) Uani 1 1 d . . . . .
I1 I 0.30407(2) 0.43064(2) 0.38290(2) 0.01887(7) Uani 1 1 d . . . . .
I2 I 0.07714(2) 0.33646(2) 0.62210(2) 0.02064(7) Uani 1 1 d . . . . .
O1 O 0.5542(3) 0.7232(3) 0.3451(2) 0.0348(7) Uani 1 1 d D . . . .
H1 H 0.643(2) 0.715(5) 0.353(3) 0.042 Uiso 1 1 d D U . . .
C1 C 0.5161(4) 0.8629(4) 0.3374(3) 0.0333(10) Uani 1 1 d . . . . .
H1A H 0.482427 0.887188 0.263491 0.040 Uiso 1 1 calc R U . . .
H1B H 0.599662 0.919493 0.365218 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4036(4) 0.8938(4) 0.3958(3) 0.0228(8) Uani 1 1 d . . . . .
N1 N 0.3766(3) 0.8005(3) 0.4645(2) 0.0189(6) Uani 1 1 d . . . . .
C3 C 0.3317(4) 1.0173(4) 0.3813(3) 0.0373(11) Uani 1 1 d . . . . .
H3 H 0.352264 1.082694 0.333338 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2300(4) 1.0435(4) 0.4376(4) 0.0423(12) Uani 1 1 d . . . . .
H4 H 0.180406 1.127672 0.428673 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2004(4) 0.9483(4) 0.5065(3) 0.0342(10) Uani 1 1 d . . . . .
H5 H 0.129698 0.964339 0.544907 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2769(3) 0.8284(3) 0.5180(3) 0.0199(8) Uani 1 1 d . . . . .
S1 S 0.25692(9) 0.69391(10) 0.60332(7) 0.02068(19) Uani 1 1 d . . . . .
C7 C 0.1330(4) 0.7588(5) 0.6752(3) 0.0378(11) Uani 1 1 d . . . . .
H7A H 0.173641 0.837807 0.716503 0.057 Uiso 1 1 calc R U . . .
H7AB H 0.110992 0.687346 0.721354 0.057 Uiso 1 1 calc R U . . .
H7AC H 0.046954 0.786699 0.626910 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu1 2.4812(9) 3_666 yes
Cu1 I1 2.5758(5) 3_666 yes
Cu1 I1 2.6389(5) . yes
Cu1 O1 2.220(3) . yes
Cu1 N1 2.009(3) . yes
Cu2 Cu2 2.6375(8) 3_566 yes
Cu2 I1 2.6256(5) . yes
Cu2 I2 2.6159(5) . yes
Cu2 I2 2.6572(5) 3_566 yes
Cu2 S1 2.3583(10) . yes
O1 H1 0.854(19) . ?
O1 C1 1.415(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.497(5) . ?
C2 N1 1.350(4) . ?
C2 C3 1.389(5) . ?
N1 C6 1.343(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(5) . ?
C6 S1 1.769(4) . ?
S1 C7 1.800(4) . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C7 H7AC 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 Cu1 I1 60.314(19) 3_666 . ?
Cu1 Cu1 I1 62.877(18) 3_666 3_666 ?
I1 Cu1 I1 123.191(18) 3_666 . yes
O1 Cu1 Cu1 125.59(9) . 3_666 ?
O1 Cu1 I1 104.85(8) . . yes
O1 Cu1 I1 107.34(7) . 3_666 yes
N1 Cu1 Cu1 154.45(9) . 3_666 ?
N1 Cu1 I1 108.89(8) . . yes
N1 Cu1 I1 122.51(8) . 3_666 yes
N1 Cu1 O1 78.49(11) . . yes
Cu2 Cu2 I2 59.216(16) 3_566 3_566 ?
I1 Cu2 Cu2 135.17(3) . 3_566 ?
I1 Cu2 I2 110.772(16) . 3_566 yes
I2 Cu2 Cu2 60.768(17) . 3_566 ?
I2 Cu2 I1 110.784(17) . . yes
I2 Cu2 I2 119.984(16) . 3_566 yes
S1 Cu2 Cu2 118.86(3) . 3_566 ?
S1 Cu2 I1 105.94(3) . . yes
S1 Cu2 I2 103.19(3) . 3_566 yes
S1 Cu2 I2 104.76(3) . . yes
Cu1 I1 Cu1 56.810(18) 3_666 . yes
Cu1 I1 Cu2 100.355(15) 3_666 . yes
Cu2 I1 Cu1 85.829(15) . . yes
Cu2 I2 Cu2 60.017(16) . 3_566 yes
Cu1 O1 H1 110(3) . . ?
C1 O1 Cu1 111.4(2) . . ?
C1 O1 H1 110(3) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.6(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 118.3(3) . . ?
N1 C2 C3 121.2(4) . . ?
C3 C2 C1 120.5(4) . . ?
C2 N1 Cu1 117.9(2) . . ?
C6 N1 Cu1 123.4(2) . . ?
C6 N1 C2 118.6(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.7(4) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 123.3(4) . . ?
N1 C6 S1 111.7(2) . . ?
C5 C6 S1 125.0(3) . . ?
C6 S1 Cu2 104.49(11) . . ?
C6 S1 C7 104.3(2) . . ?
C7 S1 Cu2 104.33(14) . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7AB 109.5 . . ?
S1 C7 H7AC 109.5 . . ?
H7A C7 H7AB 109.5 . . ?
H7A C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?

_refine_diff_density_max         0.869
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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_c38
_database_code_depnum_ccdc_archive 'CCDC 1585191'
loop_
_audit_author_name
_audit_author_address
'Denis Samsonenko' 'Nikolaev Institute of Inorganic Chemistry SB RAS'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 Cu I N S'
_chemical_formula_weight         315.63

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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4448(2)
_cell_length_b                   10.1110(2)
_cell_length_c                   11.2974(3)
_cell_angle_alpha                82.916(2)
_cell_angle_beta                 71.120(2)
_cell_angle_gamma                67.334(2)
_cell_volume                     842.24(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7820
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      30.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.489
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    6.428
_shelx_estimated_absorpt_T_min   0.241
_shelx_estimated_absorpt_T_max   0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            13803
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.782
_diffrn_reflns_theta_max         30.451
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4716
_reflns_number_gt                4377
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0142P)²+0.3711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4716
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0398
_refine_ls_wR_factor_gt          0.0389
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.42451(4) 0.11362(3) 0.11253(3) 0.01526(6) Uani 1 1 d . . . . .
Cu2 Cu 0.11929(4) 0.36774(3) 0.41667(3) 0.01530(6) Uani 1 1 d . . . . .
I1 I 0.33426(2) 0.15618(2) -0.09620(2) 0.01439(4) Uani 1 1 d . . . . .
I2 I -0.23223(2) 0.48338(2) 0.47081(2) 0.01482(4) Uani 1 1 d . . . . .
N1 N 0.5400(2) 0.24920(19) 0.13246(16) 0.0126(3) Uani 1 1 d . . . . .
C11 C 0.7196(3) 0.2057(2) 0.1062(2) 0.0154(4) Uani 1 1 d . . . . .
H11 H 0.7902 0.1083 0.0830 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8073(3) 0.2948(3) 0.1111(2) 0.0186(5) Uani 1 1 d . . . . .
H12 H 0.9346 0.2596 0.0917 0.022 Uiso 1 1 calc R U . . .
C13 C 0.7046(3) 0.4366(3) 0.1449(2) 0.0226(5) Uani 1 1 d . . . . .
H13 H 0.7608 0.5006 0.1490 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5201(3) 0.4842(3) 0.1727(2) 0.0200(5) Uani 1 1 d . . . . .
H14 H 0.4476 0.5811 0.1963 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4414(3) 0.3879(2) 0.16566(19) 0.0139(4) Uani 1 1 d . . . . .
S1 S 0.20773(7) 0.43087(6) 0.20299(5) 0.01393(10) Uani 1 1 d . . . . .
C16 C 0.1183(3) 0.6235(2) 0.2131(2) 0.0196(5) Uani 1 1 d . . . . .
H16A H -0.0107 0.6597 0.2225 0.029 Uiso 1 1 calc R U . . .
H16B H 0.1802 0.6629 0.1368 0.029 Uiso 1 1 calc R U . . .
H16C H 0.1368 0.6526 0.2857 0.029 Uiso 1 1 calc R U . . .
N2 N 0.2189(2) 0.15718(19) 0.46505(16) 0.0116(3) Uani 1 1 d . . . . .
C21 C 0.2697(3) 0.1242(2) 0.56961(19) 0.0142(4) Uani 1 1 d . . . . .
H21 H 0.2723 0.1987 0.6117 0.017 Uiso 1 1 calc R U . . .
C22 C 0.3185(3) -0.0127(2) 0.6189(2) 0.0163(4) Uani 1 1 d . . . . .
H22 H 0.3536 -0.0313 0.6930 0.020 Uiso 1 1 calc R U . . .
C23 C 0.3153(3) -0.1222(2) 0.5582(2) 0.0183(5) Uani 1 1 d . . . . .
H23 H 0.3461 -0.2169 0.5909 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2665(3) -0.0916(2) 0.4495(2) 0.0170(4) Uani 1 1 d . . . . .
H24 H 0.2642 -0.1651 0.4057 0.020 Uiso 1 1 calc R U . . .
C25 C 0.2206(3) 0.0485(2) 0.40508(19) 0.0125(4) Uani 1 1 d . . . . .
S2 S 0.16354(7) 0.10355(6) 0.26483(5) 0.01309(10) Uani 1 1 d . . . . .
C26 C 0.1473(3) -0.0539(2) 0.2195(2) 0.0184(5) Uani 1 1 d . . . . .
H26A H 0.1040 -0.0323 0.1460 0.028 Uiso 1 1 calc R U . . .
H26B H 0.0628 -0.0841 0.2886 0.028 Uiso 1 1 calc R U . . .
H26C H 0.2661 -0.1311 0.1991 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 I1 2.6432(3) . yes
Cu1 I1 2.6877(3) 2_655 yes
Cu1 N1 2.0322(18) . yes
Cu1 S2 2.3460(6) . yes
Cu2 I2 2.6229(3) . yes
Cu2 I2 2.6748(3) 2_566 yes
Cu2 S1 2.3693(6) . yes
Cu2 N2 2.0418(18) . yes
I1 Cu1 2.6877(3) 2_655 ?
I2 Cu2 2.6749(3) 2_566 ?
N1 C11 1.345(3) . ?
N1 C15 1.352(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(3) . ?
C15 S1 1.763(2) . ?
S1 C16 1.800(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 C21 1.346(3) . ?
N2 C25 1.353(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(3) . ?
C25 S2 1.767(2) . ?
S2 C26 1.798(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
I1 Cu1 I1 105.328(10) . 2_655 yes
N1 Cu1 I1 108.80(5) . 2_655 yes
N1 Cu1 I1 113.15(5) . . yes
N1 Cu1 S2 120.69(5) . . yes
S2 Cu1 I1 102.851(16) . . yes
S2 Cu1 I1 104.728(17) . 2_655 yes
I2 Cu2 I2 109.323(10) . 2_566 yes
S1 Cu2 I2 100.890(16) . . yes
S1 Cu2 I2 103.816(17) . 2_566 yes
N2 Cu2 I2 108.36(5) . 2_566 yes
N2 Cu2 I2 115.17(5) . . yes
N2 Cu2 S1 118.44(5) . . yes
Cu1 I1 Cu1 74.671(10) . 2_655 yes
Cu2 I2 Cu2 70.677(10) . 2_566 yes
C11 N1 Cu1 120.79(15) . . ?
C11 N1 C15 117.44(18) . . ?
C15 N1 Cu1 121.67(14) . . ?
N1 C11 H11 118.2 . . ?
N1 C11 C12 123.6(2) . . ?
C12 C11 H11 118.2 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 122.2(2) . . ?
N1 C15 S1 113.33(15) . . ?
C14 C15 S1 124.40(17) . . ?
C15 S1 Cu2 104.25(7) . . ?
C15 S1 C16 102.89(11) . . ?
C16 S1 Cu2 101.14(8) . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 N2 Cu2 118.75(14) . . ?
C21 N2 C25 117.16(18) . . ?
C25 N2 Cu2 123.75(14) . . ?
N2 C21 H21 118.3 . . ?
N2 C21 C22 123.4(2) . . ?
C22 C21 H21 118.3 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(2) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.9(2) . . ?
C25 C24 H24 120.6 . . ?
N2 C25 C24 122.76(19) . . ?
N2 C25 S2 112.86(15) . . ?
C24 C25 S2 124.37(17) . . ?
C25 S2 Cu1 106.46(7) . . ?
C25 S2 C26 102.45(10) . . ?
C26 S2 Cu1 102.30(8) . . ?
S2 C26 H26A 109.5 . . ?
S2 C26 H26B 109.5 . . ?
S2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_c-39
_database_code_depnum_ccdc_archive 'CCDC 1585192'
loop_
_audit_author_name
_audit_author_address
'Denis Samsonenko' 'Nikolaev Institute of Inorganic Chemistry SB RAS'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 Cu2 I2 N S'
_chemical_formula_weight         506.07

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'
S S 0.1246 0.1234 '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      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                   7.6287(6)
_cell_length_b                   7.7189(3)
_cell_length_c                   9.7933(7)
_cell_angle_alpha                102.595(5)
_cell_angle_beta                 94.694(6)
_cell_angle_gamma                104.937(5)
_cell_volume                     537.93(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      29.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.124
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    9.832
_shelx_estimated_absorpt_T_min   0.145
_shelx_estimated_absorpt_T_max   0.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            8550
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2670
_reflns_number_gt                2438
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0179P)²+0.1164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0450
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.56289(5) 0.47988(6) 0.12913(4) 0.01699(10) Uani 1 1 d . . . . .
Cu2 Cu 0.17105(5) 0.49743(6) 0.06646(5) 0.01658(10) Uani 1 1 d . . . . .
I1 I 0.46148(3) 0.77671(3) 0.10870(2) 0.01248(6) Uani 1 1 d . . . . .
I2 I -0.06014(3) 0.64107(3) 0.21310(2) 0.01271(6) Uani 1 1 d . . . . .
N1 N 0.4830(3) 0.3447(4) 0.2818(3) 0.0121(6) Uani 1 1 d . . . . .
C1 C 0.6075(4) 0.3579(5) 0.3921(4) 0.0158(7) Uani 1 1 d . . . . .
H1 H 0.7308 0.4271 0.3945 0.019 Uiso 1 1 calc R U . . .
C2 C 0.5656(5) 0.2761(5) 0.5020(4) 0.0174(7) Uani 1 1 d . . . . .
H2 H 0.6574 0.2884 0.5779 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3852(5) 0.1752(5) 0.4981(4) 0.0190(8) Uani 1 1 d . . . . .
H3 H 0.3513 0.1183 0.5725 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2556(4) 0.1580(5) 0.3858(4) 0.0159(7) Uani 1 1 d . . . . .
H4 H 0.1320 0.0882 0.3810 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3088(4) 0.2441(4) 0.2803(3) 0.0124(7) Uani 1 1 d . . . . .
S1 S 0.15541(11) 0.22029(11) 0.12670(9) 0.01334(17) Uani 1 1 d . . . . .
C6 C -0.0650(4) 0.1528(5) 0.1837(4) 0.0177(7) Uani 1 1 d . . . . .
H6A H -0.1605 0.1578 0.1126 0.027 Uiso 1 1 calc R U . . .
H6B H -0.0657 0.2376 0.2741 0.027 Uiso 1 1 calc R U . . .
H6C H -0.0888 0.0264 0.1956 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu1 2.7412(8) 2_665 yes
Cu1 Cu2 2.9015(6) 2_665 yes
Cu1 Cu2 3.0456(6) . yes
Cu1 I1 2.6413(5) . yes
Cu1 I1 2.6663(5) 2_665 yes
Cu1 I2 2.7958(5) 1_655 yes
Cu1 N1 2.049(3) . yes
Cu2 Cu1 2.9015(6) 2_665 ?
Cu2 Cu2 2.8332(8) 2_565 yes
Cu2 I1 2.5935(5) . yes
Cu2 I2 2.6703(5) . yes
Cu2 I2 2.6894(5) 2_565 yes
Cu2 S1 2.3171(9) . yes
I1 Cu1 2.6664(5) 2_665 ?
I2 Cu1 2.7958(5) 1_455 ?
I2 Cu2 2.6894(5) 2_565 ?
N1 C1 1.347(4) . ?
N1 C5 1.352(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 S1 1.774(3) . ?
S1 C6 1.800(3) . ?
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 Cu1 Cu2 59.912(17) 2_665 . ?
Cu1 Cu1 Cu2 65.260(18) 2_665 2_665 ?
Cu1 Cu1 I2 113.74(2) 2_665 1_655 ?
Cu2 Cu1 Cu2 125.172(16) 2_665 . ?
I1 Cu1 Cu1 58.459(17) 2_665 2_665 ?
I1 Cu1 Cu1 59.355(16) . 2_665 ?
I1 Cu1 Cu2 53.694(12) . . ?
I1 Cu1 Cu2 55.329(14) 2_665 2_665 ?
I1 Cu1 Cu2 94.079(16) 2_665 . ?
I1 Cu1 Cu2 98.045(16) . 2_665 ?
I1 Cu1 I1 117.813(16) . 2_665 yes
I1 Cu1 I2 99.715(16) . 1_655 yes
I1 Cu1 I2 104.283(16) 2_665 1_655 yes
I2 Cu1 Cu2 56.297(13) 1_655 2_665 ?
I2 Cu1 Cu2 152.995(19) 1_655 . ?
N1 Cu1 Cu1 141.84(8) . 2_665 ?
N1 Cu1 Cu2 88.78(7) . . ?
N1 Cu1 Cu2 139.92(8) . 2_665 ?
N1 Cu1 I1 107.50(8) . 2_665 yes
N1 Cu1 I1 120.83(8) . . yes
N1 Cu1 I2 103.97(7) . 1_655 yes
Cu1 Cu2 Cu1 54.828(16) 2_665 . ?
Cu2 Cu2 Cu1 110.11(2) 2_565 2_665 ?
Cu2 Cu2 Cu1 164.67(3) 2_565 . ?
I1 Cu2 Cu1 55.158(13) . . ?
I1 Cu2 Cu1 57.729(14) . 2_665 ?
I1 Cu2 Cu2 121.83(2) . 2_565 ?
I1 Cu2 I2 102.955(17) . . yes
I1 Cu2 I2 109.450(16) . 2_565 yes
I2 Cu2 Cu1 59.864(14) 2_565 2_665 ?
I2 Cu2 Cu1 107.742(18) 2_565 . ?
I2 Cu2 Cu1 135.751(19) . . ?
I2 Cu2 Cu1 150.500(19) . 2_665 ?
I2 Cu2 Cu2 57.762(16) 2_565 2_565 ?
I2 Cu2 Cu2 58.417(16) . 2_565 ?
I2 Cu2 I2 116.179(16) . 2_565 yes
S1 Cu2 Cu1 72.65(2) . . ?
S1 Cu2 Cu1 104.25(3) . 2_665 ?
S1 Cu2 Cu2 112.18(3) . 2_565 ?
S1 Cu2 I1 125.99(3) . . yes
S1 Cu2 I2 97.86(3) . 2_565 yes
S1 Cu2 I2 105.24(3) . . yes
Cu1 I1 Cu1 62.187(16) . 2_665 yes
Cu2 I1 Cu1 71.148(14) . . yes
Cu2 I1 Cu1 66.942(15) . 2_665 yes
Cu2 I2 Cu1 63.838(14) 2_565 1_455 yes
Cu2 I2 Cu1 118.614(16) . 1_455 yes
Cu2 I2 Cu2 63.823(16) . 2_565 yes
C1 N1 Cu1 119.3(2) . . ?
C1 N1 C5 117.1(3) . . ?
C5 N1 Cu1 123.5(2) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.5(3) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.0(3) . . ?
N1 C5 S1 114.7(2) . . ?
C4 C5 S1 122.2(2) . . ?
C5 S1 Cu2 113.53(11) . . ?
C5 S1 C6 102.39(16) . . ?
C6 S1 Cu2 105.51(12) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_c14
_database_code_depnum_ccdc_archive 'CCDC 1585525'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
'Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia.'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 complex of copper(I) iodide with 3-ethoxy-2-methylthiopyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 Cu2 I2 N O S'
_chemical_formula_sum            'C8 H11 Cu2 I2 N O S'
_chemical_formula_weight         550.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.3651(2)
_cell_length_b                   19.7496(11)
_cell_length_c                   15.8828(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.378(3)
_cell_angle_gamma                90
_cell_volume                     1363.21(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.12

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.680
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.777
_shelx_estimated_absorpt_T_min   0.063
_shelx_estimated_absorpt_T_max   0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4610
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16722
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0472
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2400
_reflns_number_gt                2277
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0205P)²+76.3277P] 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         2400
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.019
_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 -0.22842(19) 0.49187(5) 0.38065(5) 0.0296(2) Uani 1 1 d . . . . .
I2 I 0.14941(19) 0.42787(4) 0.15786(6) 0.0292(2) Uani 1 1 d . . . . .
Cu1 Cu 0.2355(4) 0.52575(9) 0.29819(13) 0.0411(5) Uani 1 1 d . . . . .
Cu2 Cu -0.3242(4) 0.49119(9) 0.20972(11) 0.0346(4) Uani 1 1 d . . . . .
S1 S 0.6309(8) 0.59876(17) 0.1487(2) 0.0289(7) Uani 1 1 d . . . . .
O1 O 0.584(3) 0.7429(5) 0.1293(7) 0.044(3) Uani 1 1 d . . . . .
N1 N 0.277(3) 0.6275(5) 0.2729(7) 0.029(2) Uani 1 1 d . . . . .
C1 C 0.424(3) 0.6540(6) 0.2116(8) 0.025(3) Uani 1 1 d . . . . .
C2 C 0.143(4) 0.6702(8) 0.3256(9) 0.039(3) Uani 1 1 d . . . . .
H8 H 0.0430 0.6523 0.3697 0.046 Uiso 1 1 calc R U . . .
C3 C 0.151(4) 0.7394(8) 0.3150(11) 0.049(4) Uani 1 1 d . . . . .
H1 H 0.0546 0.7672 0.3517 0.059 Uiso 1 1 calc R U . . .
C4 C 0.300(4) 0.7681(7) 0.2514(10) 0.040(4) Uani 1 1 d . . . . .
H2 H 0.3087 0.8148 0.2446 0.048 Uiso 1 1 calc R U . . .
C5 C 0.438(3) 0.7238(7) 0.1974(9) 0.031(3) Uani 1 1 d . . . . .
C6 C 0.611(4) 0.8142(8) 0.1100(11) 0.051(4) Uani 1 1 d . . . . .
H3 H 0.7510 0.8362 0.1524 0.062 Uiso 1 1 calc R U . . .
H4 H 0.4115 0.8361 0.1089 0.062 Uiso 1 1 calc R U . . .
C7 C 0.731(5) 0.8187(10) 0.0252(12) 0.072(6) Uani 1 1 d . . . . .
H7 H 0.9391 0.8025 0.0291 0.108 Uiso 1 1 calc R U . . .
H6 H 0.7251 0.8650 0.0066 0.108 Uiso 1 1 calc R U . . .
H5 H 0.6055 0.7915 -0.0145 0.108 Uiso 1 1 calc R U . . .
C8 C 0.386(4) 0.5971(9) 0.0512(9) 0.044(4) Uani 1 1 d . . . . .
H10 H 0.2169 0.5669 0.0567 0.067 Uiso 1 1 calc R U . . .
H11 H 0.5017 0.5818 0.0064 0.067 Uiso 1 1 calc R U . . .
H9 H 0.3089 0.6419 0.0385 0.067 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 2.5999(19) . ?
I1 Cu1 2.658(2) 1_455 ?
I1 Cu2 2.708(2) . ?
I2 Cu2 2.6145(19) . ?
I2 Cu2 2.677(2) 1_655 ?
I2 Cu1 2.948(2) . ?
Cu1 N1 2.060(11) . ?
Cu1 Cu2 2.577(3) 1_655 ?
Cu1 I1 2.658(2) 1_655 ?
Cu1 Cu2 2.787(3) . ?
Cu2 S1 2.336(4) 1_455 ?
Cu2 Cu1 2.577(3) 1_455 ?
Cu2 I2 2.677(2) 1_455 ?
S1 C1 1.781(13) . ?
S1 C8 1.797(14) . ?
S1 Cu2 2.336(4) 1_655 ?
O1 C5 1.359(17) . ?
O1 C6 1.448(17) . ?
N1 C1 1.322(17) . ?
N1 C2 1.359(18) . ?
C1 C5 1.401(18) . ?
C2 C3 1.38(2) . ?
C2 H8 0.9300 . ?
C3 C4 1.37(2) . ?
C3 H1 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H2 0.9300 . ?
C6 C7 1.49(3) . ?
C6 H3 0.9700 . ?
C6 H4 0.9700 . ?
C7 H7 0.9600 . ?
C7 H6 0.9600 . ?
C7 H5 0.9600 . ?
C8 H10 0.9600 . ?
C8 H11 0.9600 . ?
C8 H9 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu1 112.23(8) . 1_455 ?
Cu1 I1 Cu2 63.30(6) . . ?
Cu1 I1 Cu2 57.40(6) 1_455 . ?
Cu2 I2 Cu2 111.15(7) . 1_655 ?
Cu2 I2 Cu1 59.77(5) . . ?
Cu2 I2 Cu1 54.28(5) 1_655 . ?
N1 Cu1 Cu2 93.9(3) . 1_655 ?
N1 Cu1 I1 115.9(3) . . ?
Cu2 Cu1 I1 149.59(9) 1_655 . ?
N1 Cu1 I1 104.5(3) . 1_655 ?
Cu2 Cu1 I1 62.27(6) 1_655 1_655 ?
I1 Cu1 I1 112.23(8) . 1_655 ?
N1 Cu1 Cu2 103.3(3) . . ?
Cu2 Cu1 Cu2 108.88(10) 1_655 . ?
I1 Cu1 Cu2 60.24(6) . . ?
I1 Cu1 Cu2 151.24(9) 1_655 . ?
N1 Cu1 I2 119.9(3) . . ?
Cu2 Cu1 I2 57.50(6) 1_655 . ?
I1 Cu1 I2 99.33(7) . . ?
I1 Cu1 I2 104.56(7) 1_655 . ?
Cu2 Cu1 I2 54.16(5) . . ?
S1 Cu2 Cu1 86.99(11) 1_455 1_455 ?
S1 Cu2 I2 110.02(11) 1_455 . ?
Cu1 Cu2 I2 161.93(9) 1_455 . ?
S1 Cu2 I2 105.13(11) 1_455 1_455 ?
Cu1 Cu2 I2 68.22(7) 1_455 1_455 ?
I2 Cu2 I2 111.15(7) . 1_455 ?
S1 Cu2 I1 114.24(11) 1_455 . ?
Cu1 Cu2 I1 60.33(6) 1_455 . ?
I2 Cu2 I1 105.42(7) . . ?
I2 Cu2 I1 110.99(7) 1_455 . ?
S1 Cu2 Cu1 91.26(11) 1_455 . ?
Cu1 Cu2 Cu1 108.88(10) 1_455 . ?
I2 Cu2 Cu1 66.06(6) . . ?
I2 Cu2 Cu1 162.97(8) 1_455 . ?
I1 Cu2 Cu1 56.46(5) . . ?
C1 S1 C8 101.7(7) . . ?
C1 S1 Cu2 110.6(4) . 1_655 ?
C8 S1 Cu2 111.2(6) . 1_655 ?
C5 O1 C6 119.4(12) . . ?
C1 N1 C2 118.3(12) . . ?
C1 N1 Cu1 126.0(9) . . ?
C2 N1 Cu1 115.7(9) . . ?
N1 C1 C5 122.7(12) . . ?
N1 C1 S1 118.5(10) . . ?
C5 C1 S1 118.8(10) . . ?
N1 C2 C3 121.5(15) . . ?
N1 C2 H8 119.2 . . ?
C3 C2 H8 119.2 . . ?
C4 C3 C2 121.2(15) . . ?
C4 C3 H1 119.4 . . ?
C2 C3 H1 119.4 . . ?
C3 C4 C5 117.0(14) . . ?
C3 C4 H2 121.5 . . ?
C5 C4 H2 121.5 . . ?
O1 C5 C1 115.6(12) . . ?
O1 C5 C4 125.2(13) . . ?
C1 C5 C4 119.3(13) . . ?
O1 C6 C7 106.9(14) . . ?
O1 C6 H3 110.3 . . ?
C7 C6 H3 110.3 . . ?
O1 C6 H4 110.3 . . ?
C7 C6 H4 110.3 . . ?
H3 C6 H4 108.6 . . ?
C6 C7 H7 109.5 . . ?
C6 C7 H6 109.5 . . ?
H7 C7 H6 109.5 . . ?
C6 C7 H5 109.5 . . ?
H7 C7 H5 109.5 . . ?
H6 C7 H5 109.5 . . ?
S1 C8 H10 109.5 . . ?
S1 C8 H11 109.5 . . ?
H10 C8 H11 109.5 . . ?
S1 C8 H9 109.5 . . ?
H10 C8 H9 109.5 . . ?
H11 C8 H9 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C5 -2(2) . . . . ?
Cu1 N1 C1 C5 178.8(10) . . . . ?
C2 N1 C1 S1 174.2(10) . . . . ?
Cu1 N1 C1 S1 -5.1(15) . . . . ?
C8 S1 C1 N1 106.3(11) . . . . ?
Cu2 S1 C1 N1 -11.8(11) 1_655 . . . ?
C8 S1 C1 C5 -77.4(12) . . . . ?
Cu2 S1 C1 C5 164.5(9) 1_655 . . . ?
C1 N1 C2 C3 1(2) . . . . ?
Cu1 N1 C2 C3 -179.3(13) . . . . ?
N1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C6 O1 C5 C1 -179.7(13) . . . . ?
C6 O1 C5 C4 2(2) . . . . ?
N1 C1 C5 O1 -176.9(12) . . . . ?
S1 C1 C5 O1 7.0(17) . . . . ?
N1 C1 C5 C4 2(2) . . . . ?
S1 C1 C5 C4 -174.1(11) . . . . ?
C3 C4 C5 O1 177.3(15) . . . . ?
C3 C4 C5 C1 -1(2) . . . . ?
C5 O1 C6 C7 -170.5(15) . . . . ?

_refine_diff_density_max         1.742
_refine_diff_density_min         -2.028
_refine_diff_density_rms         0.231

####################################################################### 
# 
# 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_c17
_database_code_depnum_ccdc_archive 'CCDC 1585527'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
'Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia.'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 complex of copper(I) iodide with 3-phenyl-2-methylthiopyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Cu2 I2 N S'
_chemical_formula_sum            'C12 H11 Cu2 I2 N S'
_chemical_formula_weight         582.16

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'
S S 0.1246 0.1234 '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                   8.2845(3)
_cell_length_b                   7.8286(3)
_cell_length_c                   24.1700(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.4820(10)
_cell_angle_gamma                90
_cell_volume                     1557.55(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.54

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.810
_shelx_estimated_absorpt_T_min   0.343
_shelx_estimated_absorpt_T_max   0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17220
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3558
_reflns_number_gt                3231
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0385P)²+7.6663P] 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         3558
_refine_ls_number_parameters     164
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.16011(4) -0.17832(5) 0.06061(2) 0.04222(12) Uani 1 1 d . . . . .
I2 I 0.67931(4) -0.12167(5) 0.06701(2) 0.03928(12) Uani 1 1 d . . . . .
Cu1 Cu 0.89703(8) -0.13156(10) -0.00963(3) 0.04359(19) Uani 1 1 d . . . . .
Cu2 Cu 0.39908(8) 0.02569(10) 0.03888(3) 0.03917(17) Uani 1 1 d . . . . .
S1 S 0.41603(18) 0.2590(3) 0.09978(8) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.0965(6) 0.3010(6) 0.0745(2) 0.0428(11) Uani 1 1 d . . . . .
C1 C 0.455(2) 0.119(3) 0.1669(7) 0.181(7) Uani 1 1 d . U . . .
H1 H 0.4423 0.1873 0.1990 0.271 Uiso 1 1 calc R U . . .
H3 H 0.5635 0.0736 0.1698 0.271 Uiso 1 1 calc R U . . .
H2 H 0.3786 0.0261 0.1648 0.271 Uiso 1 1 calc R U . . .
C2 C 0.2218(7) 0.3412(7) 0.1121(2) 0.0381(12) Uani 1 1 d . . . . .
C3 C -0.0521(7) 0.3559(9) 0.0845(3) 0.0508(15) Uani 1 1 d . . . . .
H4 H -0.1406 0.3311 0.0585 0.061 Uiso 1 1 calc R U . . .
C4 C -0.0782(8) 0.4471(9) 0.1313(3) 0.0548(16) Uani 1 1 d . . . . .
H11 H -0.1825 0.4807 0.1373 0.066 Uiso 1 1 calc R U . . .
C5 C 0.0514(9) 0.4869(8) 0.1686(3) 0.0520(15) Uani 1 1 d . . . . .
H5 H 0.0353 0.5482 0.2004 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2068(7) 0.4379(7) 0.1600(2) 0.0402(12) Uani 1 1 d . . . . .
C7 C 0.3490(8) 0.4913(8) 0.2000(2) 0.0429(13) Uani 1 1 d . . . . .
C8 C 0.4675(9) 0.5985(8) 0.1834(3) 0.0498(14) Uani 1 1 d . . . . .
H10 H 0.4607 0.6355 0.1467 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5960(10) 0.6507(11) 0.2213(3) 0.0633(19) Uani 1 1 d . . . . .
H9 H 0.6747 0.7237 0.2101 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6072(11) 0.5942(13) 0.2759(3) 0.074(2) Uani 1 1 d . . . . .
H8 H 0.6943 0.6277 0.3013 0.089 Uiso 1 1 calc R U . . .
C11 C 0.4917(14) 0.4906(16) 0.2922(3) 0.090(3) Uani 1 1 d . . . . .
H7 H 0.4996 0.4531 0.3289 0.108 Uiso 1 1 calc R U . . .
C12 C 0.3598(11) 0.4384(12) 0.2545(3) 0.070(2) Uani 1 1 d . . . . .
H6 H 0.2800 0.3682 0.2664 0.084 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 2.6327(8) 1_455 ?
I1 Cu2 2.6422(8) . ?
I1 Cu1 2.7379(9) 3_655 ?
I2 Cu2 2.6127(7) . ?
I2 Cu2 2.6760(8) 3_655 ?
I2 Cu1 2.7286(8) . ?
Cu1 N1 2.059(5) 3_655 ?
Cu1 Cu2 2.6101(9) 3_655 ?
Cu1 I1 2.6327(8) 1_655 ?
Cu1 Cu1 2.6817(15) 3_755 ?
Cu1 I1 2.7379(9) 3_655 ?
Cu2 S1 2.3398(17) . ?
Cu2 Cu1 2.6102(9) 3_655 ?
Cu2 I2 2.6760(8) 3_655 ?
Cu2 Cu2 2.6831(13) 3_655 ?
S1 C2 1.789(6) . ?
S1 C1 1.956(17) . ?
N1 C2 1.337(7) . ?
N1 C3 1.351(7) . ?
N1 Cu1 2.059(5) 3_655 ?
C1 H1 0.9600 . ?
C1 H3 0.9600 . ?
C1 H2 0.9600 . ?
C2 C6 1.401(8) . ?
C3 C4 1.376(9) . ?
C3 H4 0.9300 . ?
C4 C5 1.357(10) . ?
C4 H11 0.9300 . ?
C5 C6 1.381(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(9) . ?
C7 C8 1.385(9) . ?
C7 C12 1.375(9) . ?
C8 C9 1.386(10) . ?
C8 H10 0.9300 . ?
C9 C10 1.387(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.346(14) . ?
C10 H8 0.9300 . ?
C11 C12 1.401(13) . ?
C11 H7 0.9300 . ?
C12 H6 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
Cu1 I1 Cu2 111.84(3) 1_455 . ?
Cu1 I1 Cu1 59.87(3) 1_455 3_655 ?
Cu2 I1 Cu1 58.01(2) . 3_655 ?
Cu2 I2 Cu2 60.96(3) . 3_655 ?
Cu2 I2 Cu1 118.16(2) . . ?
Cu2 I2 Cu1 57.75(2) 3_655 . ?
N1 Cu1 Cu2 95.91(13) 3_655 3_655 ?
N1 Cu1 I1 108.09(13) 3_655 1_655 ?
Cu2 Cu1 I1 154.57(4) 3_655 1_655 ?
N1 Cu1 Cu1 123.79(15) 3_655 3_755 ?
Cu2 Cu1 Cu1 111.30(4) 3_655 3_755 ?
I1 Cu1 Cu1 62.01(3) 1_655 3_755 ?
N1 Cu1 I2 127.69(15) 3_655 . ?
Cu2 Cu1 I2 60.12(2) 3_655 . ?
I1 Cu1 I2 97.40(3) 1_655 . ?
Cu1 Cu1 I2 108.46(4) 3_755 . ?
N1 Cu1 I1 104.25(15) 3_655 3_655 ?
Cu2 Cu1 I1 59.16(2) 3_655 3_655 ?
I1 Cu1 I1 120.13(3) 1_655 3_655 ?
Cu1 Cu1 I1 58.12(3) 3_755 3_655 ?
I2 Cu1 I1 100.75(2) . 3_655 ?
S1 Cu2 Cu1 84.86(5) . 3_655 ?
S1 Cu2 I2 101.10(5) . . ?
Cu1 Cu2 I2 172.31(4) 3_655 . ?
S1 Cu2 I1 109.86(6) . . ?
Cu1 Cu2 I1 62.83(2) 3_655 . ?
I2 Cu2 I1 110.19(3) . . ?
S1 Cu2 I2 111.92(6) . 3_655 ?
Cu1 Cu2 I2 62.14(2) 3_655 3_655 ?
I2 Cu2 I2 119.04(3) . 3_655 ?
I1 Cu2 I2 104.69(3) . 3_655 ?
S1 Cu2 Cu2 124.04(7) . 3_655 ?
Cu1 Cu2 Cu2 119.93(4) 3_655 3_655 ?
I2 Cu2 Cu2 60.69(2) . 3_655 ?
I1 Cu2 Cu2 126.07(4) . 3_655 ?
I2 Cu2 Cu2 58.36(3) 3_655 3_655 ?
C2 S1 C1 97.6(6) . . ?
C2 S1 Cu2 113.2(2) . . ?
C1 S1 Cu2 94.4(6) . . ?
C2 N1 C3 117.3(5) . . ?
C2 N1 Cu1 125.7(4) . 3_655 ?
C3 N1 Cu1 116.3(4) . 3_655 ?
S1 C1 H1 109.5 . . ?
S1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
S1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
N1 C2 C6 123.6(5) . . ?
N1 C2 S1 116.6(4) . . ?
C6 C2 S1 119.8(4) . . ?
N1 C3 C4 122.8(6) . . ?
N1 C3 H4 118.6 . . ?
C4 C3 H4 118.6 . . ?
C5 C4 C3 118.6(6) . . ?
C5 C4 H11 120.7 . . ?
C3 C4 H11 120.7 . . ?
C4 C5 C6 121.2(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C2 116.5(6) . . ?
C5 C6 C7 120.3(5) . . ?
C2 C6 C7 123.2(5) . . ?
C8 C7 C12 119.2(6) . . ?
C8 C7 C6 120.9(5) . . ?
C12 C7 C6 119.8(6) . . ?
C7 C8 C9 120.3(6) . . ?
C7 C8 H10 119.9 . . ?
C9 C8 H10 119.9 . . ?
C10 C9 C8 120.0(8) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 119.8(8) . . ?
C11 C10 H8 120.1 . . ?
C9 C10 H8 120.1 . . ?
C10 C11 C12 121.0(7) . . ?
C10 C11 H7 119.5 . . ?
C12 C11 H7 119.5 . . ?
C7 C12 C11 119.7(8) . . ?
C7 C12 H6 120.1 . . ?
C11 C12 H6 120.1 . . ?

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
C3 N1 C2 C6 -0.9(9) . . . . ?
Cu1 N1 C2 C6 -170.5(4) 3_655 . . . ?
C3 N1 C2 S1 177.2(5) . . . . ?
Cu1 N1 C2 S1 7.6(7) 3_655 . . . ?
C1 S1 C2 N1 -117.9(7) . . . . ?
Cu2 S1 C2 N1 -19.8(5) . . . . ?
C1 S1 C2 C6 60.3(8) . . . . ?
Cu2 S1 C2 C6 158.4(4) . . . . ?
C2 N1 C3 C4 -1.1(10) . . . . ?
Cu1 N1 C3 C4 169.4(6) 3_655 . . . ?
N1 C3 C4 C5 1.5(11) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C4 C5 C6 C2 -2.0(9) . . . . ?
C4 C5 C6 C7 176.7(6) . . . . ?
N1 C2 C6 C5 2.4(9) . . . . ?
S1 C2 C6 C5 -175.6(5) . . . . ?
N1 C2 C6 C7 -176.2(6) . . . . ?
S1 C2 C6 C7 5.8(8) . . . . ?
C5 C6 C7 C8 -115.6(7) . . . . ?
C2 C6 C7 C8 63.0(8) . . . . ?
C5 C6 C7 C12 62.1(9) . . . . ?
C2 C6 C7 C12 -119.3(7) . . . . ?
C12 C7 C8 C9 0.4(10) . . . . ?
C6 C7 C8 C9 178.2(6) . . . . ?
C7 C8 C9 C10 0.7(11) . . . . ?
C8 C9 C10 C11 -1.0(13) . . . . ?
C9 C10 C11 C12 0.1(16) . . . . ?
C8 C7 C12 C11 -1.3(12) . . . . ?
C6 C7 C12 C11 -179.0(8) . . . . ?
C10 C11 C12 C7 1.0(15) . . . . ?

_refine_diff_density_max         2.401
_refine_diff_density_min         -1.527
_refine_diff_density_rms         0.158

####################################################################### 
# 
# 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_c16
_database_code_depnum_ccdc_archive 'CCDC 1585526'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
'Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia.'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 complex of copper(I) iodide with 3-butoxy-2-methylthiopyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 Cu2 I2 N O S'
_chemical_formula_sum            'C10 H15 Cu2 I2 N O S'
_chemical_formula_weight         578.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   13.2768(4)
_cell_length_b                   7.4401(2)
_cell_length_c                   15.2595(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.5300(10)
_cell_angle_gamma                90
_cell_volume                     1500.33(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.04

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.560
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    7.073
_shelx_estimated_absorpt_T_min   0.083
_shelx_estimated_absorpt_T_max   0.332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4007
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20729
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         30.051
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4074
_reflns_number_gt                3766
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0253P)²+3.0438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0102(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4074
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.005
_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 0.51919(2) 0.59732(3) 0.80212(2) 0.03009(8) Uani 1 1 d . . . . .
I2 I 0.81026(2) 0.56721(3) 0.69011(2) 0.02964(8) Uani 1 1 d . . . . .
Cu1 Cu 0.63990(4) 0.77185(7) 0.70626(3) 0.03803(12) Uani 1 1 d . . . . .
Cu2 Cu 0.70062(3) 0.47206(9) 0.81300(3) 0.04671(14) Uani 1 1 d . . . . .
S1 S 0.75890(6) 0.48982(11) 0.95912(5) 0.02596(15) Uani 1 1 d . . . . .
O1 O 0.6464(2) 0.9235(3) 0.36403(15) 0.0367(6) Uani 1 1 d . . . . .
N1 N 0.57893(19) 0.8003(3) 0.57835(17) 0.0254(5) Uani 1 1 d . . . . .
C1 C 0.6289(2) 0.8641(4) 0.51246(19) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.4883(2) 0.7214(4) 0.5577(2) 0.0289(6) Uani 1 1 d . . . . .
H12 H 0.4520 0.6812 0.6031 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4473(3) 0.6980(4) 0.4720(2) 0.0324(7) Uani 1 1 d . . . . .
H11 H 0.3851 0.6410 0.4602 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4991(3) 0.7598(4) 0.4037(2) 0.0330(7) Uani 1 1 d . . . . .
H10 H 0.4733 0.7428 0.3455 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5903(2) 0.8473(4) 0.4238(2) 0.0277(6) Uani 1 1 d . . . . .
C6 C 0.6204(3) 0.8819(5) 0.2719(2) 0.0367(8) Uani 1 1 d . . . . .
H2 H 0.5536 0.9283 0.2526 0.044 Uiso 1 1 calc R U . . .
H1 H 0.6198 0.7528 0.2632 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6978(3) 0.9671(5) 0.2203(2) 0.0395(8) Uani 1 1 d . . . . .
H3 H 0.7640 0.9523 0.2524 0.047 Uiso 1 1 calc R U . . .
H4 H 0.6841 1.0950 0.2155 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7004(4) 0.8885(7) 0.1270(3) 0.0546(11) Uani 1 1 d . . . . .
H6 H 0.7485 0.9565 0.0962 0.066 Uiso 1 1 calc R U . . .
H5 H 0.7243 0.7654 0.1319 0.066 Uiso 1 1 calc R U . . .
C9 C 0.5995(4) 0.8915(8) 0.0734(3) 0.0622(13) Uani 1 1 d . . . . .
H7 H 0.5566 0.8007 0.0947 0.093 Uiso 1 1 calc R U . . .
H8 H 0.6086 0.8685 0.0128 0.093 Uiso 1 1 calc R U . . .
H9 H 0.5687 1.0074 0.0786 0.093 Uiso 1 1 calc R U . . .
C10 C 0.6646(3) 0.3720(7) 1.0148(2) 0.0440(9) Uani 1 1 d . . . . .
H13 H 0.6652 0.2469 0.9995 0.066 Uiso 1 1 calc R U . . .
H15 H 0.5990 0.4215 0.9973 0.066 Uiso 1 1 calc R U . . .
H14 H 0.6794 0.3849 1.0773 0.066 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 Cu2 2.5732(5) . ?
I1 Cu1 2.6164(5) . ?
I2 Cu2 2.5812(5) . ?
I2 Cu1 2.7506(5) 2_646 ?
I2 Cu1 2.7572(5) . ?
I2 Cu2 3.0157(7) 2_656 ?
Cu1 N1 2.051(3) . ?
Cu1 Cu2 2.6285(7) 2_656 ?
Cu1 I2 2.7506(5) 2_656 ?
Cu1 Cu2 2.8328(7) . ?
Cu2 S1 2.2924(9) . ?
Cu2 Cu1 2.6285(6) 2_646 ?
Cu2 I2 3.0158(7) 2_646 ?
S1 C1 1.777(3) 2_646 ?
S1 C10 1.807(4) . ?
O1 C5 1.356(4) . ?
O1 C6 1.448(4) . ?
N1 C1 1.343(4) . ?
N1 C2 1.349(4) . ?
C1 C5 1.405(4) . ?
C1 S1 1.777(3) 2_656 ?
C2 C3 1.379(5) . ?
C2 H12 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H11 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H10 0.9300 . ?
C6 C7 1.495(6) . ?
C6 H2 0.9700 . ?
C6 H1 0.9700 . ?
C7 C8 1.543(6) . ?
C7 H3 0.9700 . ?
C7 H4 0.9700 . ?
C8 C9 1.501(7) . ?
C8 H6 0.9700 . ?
C8 H5 0.9700 . ?
C9 H7 0.9600 . ?
C9 H8 0.9600 . ?
C9 H9 0.9600 . ?
C10 H13 0.9600 . ?
C10 H15 0.9600 . ?
C10 H14 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu2 I1 Cu1 66.160(17) . . ?
Cu2 I2 Cu1 58.972(16) . 2_646 ?
Cu2 I2 Cu1 63.997(15) . . ?
Cu1 I2 Cu1 122.942(11) 2_646 . ?
Cu2 I2 Cu2 104.825(16) . 2_656 ?
Cu1 I2 Cu2 144.641(16) 2_646 2_656 ?
Cu1 I2 Cu2 53.944(13) . 2_656 ?
N1 Cu1 I1 112.12(8) . . ?
N1 Cu1 Cu2 94.78(8) . 2_656 ?
I1 Cu1 Cu2 152.53(2) . 2_656 ?
N1 Cu1 I2 121.04(8) . 2_656 ?
I1 Cu1 I2 101.625(17) . 2_656 ?
Cu2 Cu1 I2 57.299(15) 2_656 2_656 ?
N1 Cu1 I2 102.94(8) . . ?
I1 Cu1 I2 109.140(18) . . ?
Cu2 Cu1 I2 68.057(18) 2_656 . ?
I2 Cu1 I2 109.787(16) 2_656 . ?
N1 Cu1 Cu2 133.87(8) . . ?
I1 Cu1 Cu2 56.189(14) . . ?
Cu2 Cu1 Cu2 108.833(18) 2_656 . ?
I2 Cu1 Cu2 105.017(19) 2_656 . ?
I2 Cu1 Cu2 54.980(14) . . ?
S1 Cu2 I1 105.55(3) . . ?
S1 Cu2 I2 121.99(3) . . ?
I1 Cu2 I2 116.341(19) . . ?
S1 Cu2 Cu1 86.64(3) . 2_646 ?
I1 Cu2 Cu1 163.18(3) . 2_646 ?
I2 Cu2 Cu1 63.731(16) . 2_646 ?
S1 Cu2 Cu1 124.37(3) . . ?
I1 Cu2 Cu1 57.651(15) . . ?
I2 Cu2 Cu1 61.022(15) . . ?
Cu1 Cu2 Cu1 124.724(18) 2_646 . ?
S1 Cu2 I2 94.82(3) . 2_646 ?
I1 Cu2 I2 108.52(2) . 2_646 ?
I2 Cu2 I2 106.978(19) . 2_646 ?
Cu1 Cu2 I2 57.999(17) 2_646 2_646 ?
Cu1 Cu2 I2 140.07(2) . 2_646 ?
C1 S1 C10 103.44(18) 2_646 . ?
C1 S1 Cu2 113.80(10) 2_646 . ?
C10 S1 Cu2 104.21(13) . . ?
C5 O1 C6 117.9(3) . . ?
C1 N1 C2 118.2(3) . . ?
C1 N1 Cu1 124.8(2) . . ?
C2 N1 Cu1 116.0(2) . . ?
N1 C1 C5 121.9(3) . . ?
N1 C1 S1 117.8(2) . 2_656 ?
C5 C1 S1 120.1(2) . 2_656 ?
N1 C2 C3 122.6(3) . . ?
N1 C2 H12 118.7 . . ?
C3 C2 H12 118.7 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H11 120.2 . . ?
C4 C3 H11 120.2 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H10 120.7 . . ?
C5 C4 H10 120.7 . . ?
O1 C5 C4 125.0(3) . . ?
O1 C5 C1 115.9(3) . . ?
C4 C5 C1 119.1(3) . . ?
O1 C6 C7 108.0(3) . . ?
O1 C6 H2 110.1 . . ?
C7 C6 H2 110.1 . . ?
O1 C6 H1 110.1 . . ?
C7 C6 H1 110.1 . . ?
H2 C6 H1 108.4 . . ?
C6 C7 C8 113.8(3) . . ?
C6 C7 H3 108.8 . . ?
C8 C7 H3 108.8 . . ?
C6 C7 H4 108.8 . . ?
C8 C7 H4 108.8 . . ?
H3 C7 H4 107.7 . . ?
C9 C8 C7 113.5(4) . . ?
C9 C8 H6 108.9 . . ?
C7 C8 H6 108.9 . . ?
C9 C8 H5 108.9 . . ?
C7 C8 H5 108.9 . . ?
H6 C8 H5 107.7 . . ?
C8 C9 H7 109.5 . . ?
C8 C9 H8 109.5 . . ?
H7 C9 H8 109.5 . . ?
C8 C9 H9 109.5 . . ?
H7 C9 H9 109.5 . . ?
H8 C9 H9 109.5 . . ?
S1 C10 H13 109.5 . . ?
S1 C10 H15 109.5 . . ?
H13 C10 H15 109.5 . . ?
S1 C10 H14 109.5 . . ?
H13 C10 H14 109.5 . . ?
H15 C10 H14 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C5 -1.3(4) . . . . ?
Cu1 N1 C1 C5 167.1(2) . . . . ?
C2 N1 C1 S1 173.1(2) . . . 2_656 ?
Cu1 N1 C1 S1 -18.6(3) . . . 2_656 ?
C1 N1 C2 C3 2.5(4) . . . . ?
Cu1 N1 C2 C3 -166.8(2) . . . . ?
N1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C6 O1 C5 C4 -12.6(5) . . . . ?
C6 O1 C5 C1 168.7(3) . . . . ?
C3 C4 C5 O1 -176.2(3) . . . . ?
C3 C4 C5 C1 2.5(5) . . . . ?
N1 C1 C5 O1 177.6(3) . . . . ?
S1 C1 C5 O1 3.3(4) 2_656 . . . ?
N1 C1 C5 C4 -1.2(5) . . . . ?
S1 C1 C5 C4 -175.5(2) 2_656 . . . ?
C5 O1 C6 C7 -174.9(3) . . . . ?
O1 C6 C7 C8 162.0(3) . . . . ?
C6 C7 C8 C9 54.2(5) . . . . ?

_refine_diff_density_max         1.376
_refine_diff_density_min         -1.141
_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_clu1
_database_code_depnum_ccdc_archive 'CCDC 1585530'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
'Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia.'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
complex of copper(I) iodide with 6-methyl-2-methylthiopyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 Cu2 I2 N S'
_chemical_formula_sum            'C7 H9 Cu2 I2 N S'
_chemical_formula_weight         520.09

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'
S S 0.1246 0.1234 '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      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                   7.3111(4)
_cell_length_b                   8.5758(5)
_cell_length_c                   10.1694(6)
_cell_angle_alpha                77.594(2)
_cell_angle_beta                 79.841(2)
_cell_angle_gamma                89.519(2)
_cell_volume                     612.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8582
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      27.52

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.819
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    8.637
_shelx_estimated_absorpt_T_min   0.152
_shelx_estimated_absorpt_T_max   0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4991
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11000
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.832
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2688
_reflns_number_gt                2490
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0349P)²+0.7862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0159(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.006
_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 -0.21726(4) 0.20043(3) 0.70353(3) 0.04338(11) Uani 1 1 d . . . . .
I2 I 0.35256(3) 0.29800(3) 0.45408(2) 0.03632(11) Uani 1 1 d . . . . .
Cu1 Cu 0.32895(8) 0.59154(6) 0.49212(5) 0.04415(15) Uani 1 1 d . . . . .
Cu2 Cu 0.11688(7) 0.29658(6) 0.66993(5) 0.04029(14) Uani 1 1 d . . . . .
S1 S 0.11347(13) 0.63070(12) 0.68381(10) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.2000(4) 0.3654(4) 0.8281(3) 0.0306(6) Uani 1 1 d . . . . .
C1 C 0.1905(5) 0.5209(5) 0.8303(4) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.2503(5) 0.2610(5) 0.9339(4) 0.0394(9) Uani 1 1 d . . . . .
C3 C 0.2637(7) 0.0914(6) 0.9218(5) 0.0539(11) Uani 1 1 d . . . . .
H2 H 0.1494 0.0565 0.9016 0.081 Uiso 1 1 calc R U . . .
H1 H 0.2861 0.0264 1.0065 0.081 Uiso 1 1 calc R U . . .
H3 H 0.3642 0.0819 0.8495 0.081 Uiso 1 1 calc R U . . .
C4 C 0.2899(6) 0.3138(7) 1.0466(4) 0.0502(11) Uani 1 1 d . . . . .
H4 H 0.3239 0.2415 1.1199 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2782(6) 0.4741(7) 1.0486(4) 0.0516(12) Uani 1 1 d . . . . .
H5 H 0.3029 0.5101 1.1239 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2299(6) 0.5805(6) 0.9392(4) 0.0464(10) Uani 1 1 d . . . . .
H6 H 0.2237 0.6891 0.9382 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1466(9) 0.8356(6) 0.6921(6) 0.0638(14) Uani 1 1 d . . . . .
H7 H 0.0587 0.8598 0.7665 0.096 Uiso 1 1 calc R U . . .
H8 H 0.1282 0.9042 0.6078 0.096 Uiso 1 1 calc R U . . .
H9 H 0.2706 0.8524 0.7065 0.096 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 Cu2 2.5265(6) . ?
I1 Cu1 2.6138(6) 2_566 ?
I2 Cu2 2.5381(6) . ?
I2 Cu1 2.6276(6) . ?
I2 Cu1 2.7070(6) 2_666 ?
Cu1 S1 2.3630(11) . ?
Cu1 I1 2.6137(6) 2_566 ?
Cu1 I2 2.7070(6) 2_666 ?
Cu1 Cu1 2.9520(11) 2_666 ?
Cu1 Cu2 3.0305(8) . ?
Cu2 N1 2.015(3) . ?
S1 C1 1.763(4) . ?
S1 C7 1.798(5) . ?
N1 C1 1.340(5) . ?
N1 C2 1.347(5) . ?
C1 C6 1.388(5) . ?
C2 C4 1.395(6) . ?
C2 C3 1.487(7) . ?
C3 H2 0.9600 . ?
C3 H1 0.9600 . ?
C3 H3 0.9600 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9600 . ?
C7 H8 0.9600 . ?
C7 H9 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu2 I1 Cu1 99.629(19) . 2_566 ?
Cu2 I2 Cu1 71.816(18) . . ?
Cu2 I2 Cu1 103.950(17) . 2_666 ?
Cu1 I2 Cu1 67.18(2) . 2_666 ?
S1 Cu1 I1 100.67(3) . 2_566 ?
S1 Cu1 I2 116.32(3) . . ?
I1 Cu1 I2 115.16(2) 2_566 . ?
S1 Cu1 I2 100.86(3) . 2_666 ?
I1 Cu1 I2 109.51(2) 2_566 2_666 ?
I2 Cu1 I2 112.82(2) . 2_666 ?
S1 Cu1 Cu1 124.57(4) . 2_666 ?
I1 Cu1 Cu1 133.20(3) 2_566 2_666 ?
I2 Cu1 Cu1 57.694(18) . 2_666 ?
I2 Cu1 Cu1 55.129(19) 2_666 2_666 ?
S1 Cu1 Cu2 63.61(3) . . ?
I1 Cu1 Cu2 127.23(2) 2_566 . ?
I2 Cu1 Cu2 52.721(15) . . ?
I2 Cu1 Cu2 122.56(2) 2_666 . ?
Cu1 Cu1 Cu2 87.39(2) 2_666 . ?
N1 Cu2 I1 117.31(8) . . ?
N1 Cu2 I2 119.09(8) . . ?
I1 Cu2 I2 123.53(2) . . ?
N1 Cu2 Cu1 85.88(9) . . ?
I1 Cu2 Cu1 132.53(2) . . ?
I2 Cu2 Cu1 55.463(15) . . ?
C1 S1 C7 104.0(2) . . ?
C1 S1 Cu1 106.84(12) . . ?
C7 S1 Cu1 105.74(19) . . ?
C1 N1 C2 119.8(3) . . ?
C1 N1 Cu2 117.2(2) . . ?
C2 N1 Cu2 122.8(3) . . ?
N1 C1 C6 122.4(4) . . ?
N1 C1 S1 111.0(3) . . ?
C6 C1 S1 126.5(3) . . ?
N1 C2 C4 120.3(4) . . ?
N1 C2 C3 116.7(4) . . ?
C4 C2 C3 123.0(4) . . ?
C2 C3 H2 109.5 . . ?
C2 C3 H1 109.5 . . ?
H2 C3 H1 109.5 . . ?
C2 C3 H3 109.5 . . ?
H2 C3 H3 109.5 . . ?
H1 C3 H3 109.5 . . ?
C5 C4 C2 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C2 C4 H4 120.3 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.0(4) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
S1 C7 H7 109.5 . . ?
S1 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
S1 C7 H9 109.5 . . ?
H7 C7 H9 109.5 . . ?
H8 C7 H9 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C6 -0.4(5) . . . . ?
Cu2 N1 C1 C6 174.8(3) . . . . ?
C2 N1 C1 S1 -177.8(3) . . . . ?
Cu2 N1 C1 S1 -2.6(3) . . . . ?
C7 S1 C1 N1 -170.9(3) . . . . ?
Cu1 S1 C1 N1 -59.3(3) . . . . ?
C7 S1 C1 C6 11.9(4) . . . . ?
Cu1 S1 C1 C6 123.4(3) . . . . ?
C1 N1 C2 C4 0.9(5) . . . . ?
Cu2 N1 C2 C4 -174.0(3) . . . . ?
C1 N1 C2 C3 -178.0(3) . . . . ?
Cu2 N1 C2 C3 7.1(5) . . . . ?
N1 C2 C4 C5 -0.4(6) . . . . ?
C3 C2 C4 C5 178.5(4) . . . . ?
C2 C4 C5 C6 -0.8(6) . . . . ?
N1 C1 C6 C5 -0.7(6) . . . . ?
S1 C1 C6 C5 176.2(3) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_c54
_database_code_depnum_ccdc_archive 'CCDC 1585529'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
'Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia.'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 complex of copper(I) iodide with 6-methyl-2-butylthiopyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 Cu3 I3 N2 S2'
_chemical_formula_sum            'C20 H30 Cu3 I3 N2 S2'
_chemical_formula_weight         933.90

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'
S S 0.1246 0.1234 '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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   9.6879(5)
_cell_length_b                   10.7084(6)
_cell_length_c                   13.9460(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.975(2)
_cell_angle_gamma                90
_cell_volume                     1409.85(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.200
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.686
_shelx_estimated_absorpt_T_min   0.163
_shelx_estimated_absorpt_T_max   0.483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5114
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30118
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4126
_reflns_number_gt                3612
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0235P)²+0.5764P] 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         4126
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0515
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.2500 0.55831(2) 0.2500 0.04084(6) Uani 1 2 d S T P . .
I2 I 0.58571(2) 0.84971(2) 0.33323(2) 0.04558(5) Uani 1 1 d . . . . .
Cu1 Cu 0.41538(3) 0.71902(3) 0.20767(2) 0.04068(7) Uani 1 1 d . . . . .
Cu2 Cu 0.7500 0.71076(4) 0.2500 0.03910(9) Uani 1 2 d S T P . .
S1 S 0.62413(5) 0.58447(5) 0.11771(4) 0.03300(10) Uani 1 1 d . . . . .
N1 N 0.43858(17) 0.76134(15) 0.07125(12) 0.0313(3) Uani 1 1 d . . . . .
C1 C 0.5386(2) 0.70131(19) 0.03571(14) 0.0320(4) Uani 1 1 d . . . . .
C2 C 0.5678(2) 0.7298(2) -0.05477(16) 0.0423(5) Uani 1 1 d . . . . .
H2A H 0.6359 0.6858 -0.0785 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4916(3) 0.8264(2) -0.10862(17) 0.0489(6) Uani 1 1 d . . . . .
H3A H 0.5084 0.8484 -0.1695 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3912(3) 0.8895(2) -0.07170(17) 0.0464(5) Uani 1 1 d . . . . .
H4A H 0.3406 0.9547 -0.1073 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3660(2) 0.8559(2) 0.01843(16) 0.0374(4) Uani 1 1 d . . . . .
C6 C 0.2596(3) 0.9216(2) 0.0638(2) 0.0497(6) Uani 1 1 d . . . . .
H6A H 0.2145 0.9866 0.0204 0.075 Uiso 1 1 calc R U . . .
H6B H 0.1896 0.8629 0.0743 0.075 Uiso 1 1 calc R U . . .
H6C H 0.3067 0.9574 0.1256 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7568(2) 0.5206(2) 0.05740(16) 0.0380(4) Uani 1 1 d . . . . .
H7A H 0.7113 0.4887 -0.0070 0.046 Uiso 1 1 calc R U . . .
H7B H 0.8227 0.5857 0.0488 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8361(2) 0.4159(2) 0.12022(16) 0.0385(4) Uani 1 1 d . . . . .
H8A H 0.8835 0.4490 0.1838 0.046 Uiso 1 1 calc R U . . .
H8B H 0.7691 0.3529 0.1309 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9448(3) 0.3564(2) 0.07088(17) 0.0425(5) Uani 1 1 d . . . . .
H9A H 0.8972 0.3277 0.0059 0.051 Uiso 1 1 calc R U . . .
H9B H 1.0132 0.4193 0.0627 0.051 Uiso 1 1 calc R U . . .
C10 C 1.0231(3) 0.2473(3) 0.1278(2) 0.0574(7) Uani 1 1 d . . . . .
H10A H 1.0898 0.2142 0.0928 0.086 Uiso 1 1 calc R U . . .
H10B H 1.0727 0.2751 0.1917 0.086 Uiso 1 1 calc R U . . .
H10C H 0.9565 0.1834 0.1348 0.086 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 2.5104(3) . ?
I1 Cu1 2.5104(3) 2 ?
I2 Cu1 2.5397(3) . ?
I2 Cu2 2.6314(3) . ?
Cu1 N1 2.0168(16) . ?
Cu2 S1 2.3894(6) 2_655 ?
Cu2 S1 2.3894(6) . ?
Cu2 I2 2.6314(3) 2_655 ?
S1 C1 1.771(2) . ?
S1 C7 1.820(2) . ?
N1 C1 1.347(3) . ?
N1 C5 1.352(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.389(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.500(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu1 93.442(15) . 2 ?
Cu1 I2 Cu2 75.402(9) . . ?
N1 Cu1 I1 126.02(5) . . ?
N1 Cu1 I2 109.50(5) . . ?
I1 Cu1 I2 124.458(12) . . ?
S1 Cu2 S1 111.06(3) 2_655 . ?
S1 Cu2 I2 103.523(13) 2_655 . ?
S1 Cu2 I2 113.970(12) . . ?
S1 Cu2 I2 113.970(12) 2_655 2_655 ?
S1 Cu2 I2 103.523(13) . 2_655 ?
I2 Cu2 I2 111.129(16) . 2_655 ?
C1 S1 C7 104.11(10) . . ?
C1 S1 Cu2 100.52(7) . . ?
C7 S1 Cu2 106.17(7) . . ?
C1 N1 C5 119.08(18) . . ?
C1 N1 Cu1 118.80(13) . . ?
C5 N1 Cu1 121.83(14) . . ?
N1 C1 C2 122.7(2) . . ?
N1 C1 S1 111.76(14) . . ?
C2 C1 S1 125.55(17) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 H2A 121.2 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 120.9(2) . . ?
N1 C5 C6 116.4(2) . . ?
C4 C5 C6 122.7(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 S1 109.17(14) . . ?
C8 C7 H7A 109.8 . . ?
S1 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
S1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 111.09(18) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 113.7(2) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -2.0(3) . . . . ?
Cu1 N1 C1 C2 -175.94(16) . . . . ?
C5 N1 C1 S1 178.22(14) . . . . ?
Cu1 N1 C1 S1 4.28(18) . . . . ?
C7 S1 C1 N1 -178.11(14) . . . . ?
Cu2 S1 C1 N1 -68.31(14) . . . . ?
C7 S1 C1 C2 2.1(2) . . . . ?
Cu2 S1 C1 C2 111.92(18) . . . . ?
N1 C1 C2 C3 1.5(3) . . . . ?
S1 C1 C2 C3 -178.80(18) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C1 N1 C5 C4 1.3(3) . . . . ?
Cu1 N1 C5 C4 175.01(16) . . . . ?
C1 N1 C5 C6 -177.99(19) . . . . ?
Cu1 N1 C5 C6 -4.2(3) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C3 C4 C5 C6 179.2(2) . . . . ?
C1 S1 C7 C8 -178.65(15) . . . . ?
Cu2 S1 C7 C8 75.76(15) . . . . ?
S1 C7 C8 C9 177.96(16) . . . . ?
C7 C8 C9 C10 -177.4(2) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_c15
_database_code_depnum_ccdc_archive 'CCDC 2165799'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 Complex of Cu(I) iodide with 3-methoxy-6-methyl-2-(methylthio)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 Cu2 I2 N O S'
_chemical_formula_sum            'C8 H11 Cu2 I2 N O S'
_chemical_formula_weight         550.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6275(3)
_cell_length_b                   16.1635(4)
_cell_length_c                   8.2621(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.2260(10)
_cell_angle_gamma                90
_cell_volume                     1387.05(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate-prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.634
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.643
_shelx_estimated_absorpt_T_min   0.064
_shelx_estimated_absorpt_T_max   0.515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3809
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15989
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3182
_reflns_number_gt                2824
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0145P)²+3.3522P] 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         3182
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0535
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.015
_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 0.01104(2) 0.31373(2) 0.67649(4) 0.04578(8) Uani 1 1 d . . . . .
I2 I 0.36965(2) 0.23365(2) 0.53463(3) 0.03391(7) Uani 1 1 d . . . . .
Cu1 Cu 0.21084(5) 0.21733(3) 0.75755(5) 0.03750(11) Uani 1 1 d . . . . .
Cu2 Cu 0.20495(5) 0.35029(3) 0.56173(6) 0.03971(11) Uani 1 1 d . . . . .
S1 S 0.15361(10) 0.41900(5) 0.19557(11) 0.0389(2) Uani 1 1 d . . . . .
O1 O 0.2553(3) 0.58199(16) 0.1364(3) 0.0483(7) Uani 1 1 d . . . . .
N1 N 0.2666(3) 0.46191(16) 0.5063(3) 0.0317(6) Uani 1 1 d . . . . .
C1 C 0.3362(4) 0.5107(2) 0.6249(5) 0.0407(8) Uani 1 1 d . . . . .
C2 C 0.3825(5) 0.5856(3) 0.5823(6) 0.0544(11) Uani 1 1 d . . . . .
H1 H 0.431536 0.618531 0.664330 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3577(4) 0.6122(2) 0.4215(6) 0.0522(11) Uani 1 1 d . . . . .
H2 H 0.388412 0.663128 0.394429 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2862(3) 0.5624(2) 0.2998(4) 0.0353(7) Uani 1 1 d . . . . .
C5 C 0.2885(5) 0.6627(3) 0.0897(6) 0.0601(12) Uani 1 1 d . . . . .
H3 H 0.243059 0.703328 0.139933 0.090 Uiso 1 1 calc R U . . .
H4 H 0.265124 0.668075 -0.028632 0.090 Uiso 1 1 calc R U . . .
H5 H 0.379489 0.671007 0.126212 0.090 Uiso 1 1 calc R U . . .
C6 C 0.2426(3) 0.48657(19) 0.3471(4) 0.0291(7) Uani 1 1 d . . . . .
C7 C -0.0086(4) 0.4393(3) 0.2189(7) 0.0641(14) Uani 1 1 d . . . . .
H8 H -0.018037 0.421377 0.326463 0.096 Uiso 1 1 calc R U . . .
H7 H -0.068298 0.409868 0.135281 0.096 Uiso 1 1 calc R U . . .
H6 H -0.025683 0.497607 0.207464 0.096 Uiso 1 1 calc R U . . .
C8 C 0.3617(5) 0.4791(3) 0.7996(5) 0.0605(13) Uani 1 1 d . . . . .
H9 H 0.281327 0.469030 0.831600 0.091 Uiso 1 1 calc R U . . .
H10 H 0.410058 0.519586 0.872239 0.091 Uiso 1 1 calc R U . . .
H11 H 0.409931 0.428574 0.806628 0.091 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 Cu2 2.5145(5) . ?
I1 Cu1 2.6045(5) . ?
I2 Cu2 2.6141(5) . ?
I2 Cu1 2.6609(5) 4_565 ?
I2 Cu1 2.7617(5) . ?
Cu1 S1 2.3142(10) 4_566 ?
Cu1 Cu2 2.6827(6) . ?
Cu1 Cu2 2.7534(6) 4_566 ?
Cu2 N1 2.005(3) . ?
S1 C6 1.776(3) . ?
S1 C7 1.805(5) . ?
O1 C4 1.358(4) . ?
O1 C5 1.425(5) . ?
N1 C6 1.346(4) . ?
N1 C1 1.350(4) . ?
C1 C2 1.380(6) . ?
C1 C8 1.501(5) . ?
C2 C3 1.368(6) . ?
C2 H1 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H2 0.9300 . ?
C4 C6 1.395(4) . ?
C5 H3 0.9600 . ?
C5 H4 0.9600 . ?
C5 H5 0.9600 . ?
C7 H8 0.9600 . ?
C7 H7 0.9600 . ?
C7 H6 0.9600 . ?
C8 H9 0.9600 . ?
C8 H10 0.9600 . ?
C8 H11 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu2 I1 Cu1 63.183(16) . . ?
Cu2 I2 Cu1 62.922(15) . 4_565 ?
Cu2 I2 Cu1 59.798(14) . . ?
Cu1 I2 Cu1 103.674(18) 4_565 . ?
S1 Cu1 I1 110.55(3) 4_566 . ?
S1 Cu1 I2 124.26(3) 4_566 4_566 ?
I1 Cu1 I2 112.156(18) . 4_566 ?
S1 Cu1 Cu2 131.13(3) 4_566 . ?
I1 Cu1 Cu2 56.771(15) . . ?
I2 Cu1 Cu2 102.115(19) 4_566 . ?
S1 Cu1 Cu2 76.61(3) 4_566 4_566 ?
I1 Cu1 Cu2 107.30(2) . 4_566 ?
I2 Cu1 Cu2 57.707(14) 4_566 4_566 ?
Cu2 Cu1 Cu2 150.03(2) . 4_566 ?
S1 Cu1 I2 96.46(3) 4_566 . ?
I1 Cu1 I2 110.575(17) . . ?
I2 Cu1 I2 100.341(18) 4_566 . ?
Cu2 Cu1 I2 57.368(15) . . ?
Cu2 Cu1 I2 141.44(2) 4_566 . ?
N1 Cu2 I1 129.13(9) . . ?
N1 Cu2 I2 111.85(9) . . ?
I1 Cu2 I2 118.682(18) . . ?
N1 Cu2 Cu1 153.06(8) . . ?
I1 Cu2 Cu1 60.046(15) . . ?
I2 Cu2 Cu1 62.834(15) . . ?
N1 Cu2 Cu1 94.41(8) . 4_565 ?
I1 Cu2 Cu1 115.45(2) . 4_565 ?
I2 Cu2 Cu1 59.370(15) . 4_565 ?
Cu1 Cu2 Cu1 103.319(15) . 4_565 ?
C6 S1 C7 101.01(19) . . ?
C6 S1 Cu1 110.72(11) . 4_565 ?
C7 S1 Cu1 111.23(16) . 4_565 ?
C4 O1 C5 117.5(3) . . ?
C6 N1 C1 119.8(3) . . ?
C6 N1 Cu2 119.1(2) . . ?
C1 N1 Cu2 121.0(2) . . ?
N1 C1 C2 119.8(4) . . ?
N1 C1 C8 117.3(3) . . ?
C2 C1 C8 122.9(4) . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H1 119.4 . . ?
C1 C2 H1 119.4 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H2 120.5 . . ?
C4 C3 H2 120.5 . . ?
O1 C4 C3 124.5(3) . . ?
O1 C4 C6 117.3(3) . . ?
C3 C4 C6 118.1(3) . . ?
O1 C5 H3 109.5 . . ?
O1 C5 H4 109.5 . . ?
H3 C5 H4 109.5 . . ?
O1 C5 H5 109.5 . . ?
H3 C5 H5 109.5 . . ?
H4 C5 H5 109.5 . . ?
N1 C6 C4 121.9(3) . . ?
N1 C6 S1 118.0(2) . . ?
C4 C6 S1 120.1(3) . . ?
S1 C7 H8 109.5 . . ?
S1 C7 H7 109.5 . . ?
H8 C7 H7 109.5 . . ?
S1 C7 H6 109.5 . . ?
H8 C7 H6 109.5 . . ?
H7 C7 H6 109.5 . . ?
C1 C8 H9 109.5 . . ?
C1 C8 H10 109.5 . . ?
H9 C8 H10 109.5 . . ?
C1 C8 H11 109.5 . . ?
H9 C8 H11 109.5 . . ?
H10 C8 H11 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C2 -0.1(6) . . . . ?
Cu2 N1 C1 C2 177.0(3) . . . . ?
C6 N1 C1 C8 -178.9(4) . . . . ?
Cu2 N1 C1 C8 -1.9(5) . . . . ?
N1 C1 C2 C3 1.0(7) . . . . ?
C8 C1 C2 C3 179.8(5) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C5 O1 C4 C3 -6.2(6) . . . . ?
C5 O1 C4 C6 173.9(4) . . . . ?
C2 C3 C4 O1 180.0(4) . . . . ?
C2 C3 C4 C6 -0.1(6) . . . . ?
C1 N1 C6 C4 -0.9(5) . . . . ?
Cu2 N1 C6 C4 -178.1(3) . . . . ?
C1 N1 C6 S1 178.7(3) . . . . ?
Cu2 N1 C6 S1 1.5(4) . . . . ?
O1 C4 C6 N1 -179.1(3) . . . . ?
C3 C4 C6 N1 1.0(6) . . . . ?
O1 C4 C6 S1 1.3(5) . . . . ?
C3 C4 C6 S1 -178.6(3) . . . . ?
C7 S1 C6 N1 79.9(3) . . . . ?
Cu1 S1 C6 N1 -38.0(3) 4_565 . . . ?
C7 S1 C6 C4 -100.5(3) . . . . ?
Cu1 S1 C6 C4 141.6(3) 4_565 . . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_c37
_database_code_depnum_ccdc_archive 'CCDC 2165800'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 Complex of Cu(I) iodide with 2-methyl-6-(methylthio)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 Cu2 I2 N S'
_chemical_formula_sum            'C7 H9 Cu2 I2 N S'
_chemical_formula_weight         520.09

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'
S S 0.1246 0.1234 '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      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                   7.2585(3)
_cell_length_b                   8.4812(4)
_cell_length_c                   10.1289(4)
_cell_angle_alpha                78.0630(10)
_cell_angle_beta                 79.3810(10)
_cell_angle_gamma                88.7400(10)
_cell_volume                     599.53(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    8290
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      32.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.881
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.826
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4366
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12782
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         32.758
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3922
_reflns_number_gt                3560
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0288P)²+0.0392P] 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         3922
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_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 1.22046(2) 0.29963(2) 0.29816(2) 0.01717(5) Uani 1 1 d . . . . .
I2 I 1.35524(2) -0.20724(2) 0.45127(2) 0.01472(5) Uani 1 1 d . . . . .
Cu1 Cu 1.33269(5) 0.08823(4) 0.49378(3) 0.01704(8) Uani 1 1 d . . . . .
Cu2 Cu 0.88229(4) 0.21004(4) 0.33017(3) 0.01650(7) Uani 1 1 d . . . . .
S1 S 1.11015(9) 0.12736(8) 0.68424(6) 0.01495(12) Uani 1 1 d . . . . .
N1 N 0.8007(3) 0.1402(3) 0.1717(2) 0.0133(4) Uani 1 1 d . . . . .
C1 C 1.1369(4) 0.3347(4) 0.6948(3) 0.0257(6) Uani 1 1 d . . . . .
H3 H 1.051595 0.356410 0.775788 0.039 Uiso 1 1 calc R U . . .
H1 H 1.107178 0.405184 0.612061 0.039 Uiso 1 1 calc R U . . .
H2 H 1.266492 0.355275 0.702360 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8107(3) -0.0176(3) 0.1694(2) 0.0144(5) Uani 1 1 d . . . . .
C3 C 0.7719(3) -0.0802(4) 0.0601(3) 0.0183(5) Uani 1 1 d . . . . .
H9 H 0.779869 -0.192325 0.060940 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7213(4) 0.0279(4) -0.0496(3) 0.0216(6) Uani 1 1 d . . . . .
H4 H 0.694997 -0.009890 -0.126298 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7090(4) 0.1906(4) -0.0478(3) 0.0205(5) Uani 1 1 d . . . . .
H5 H 0.674184 0.264851 -0.122764 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7483(3) 0.2441(3) 0.0652(3) 0.0162(5) Uani 1 1 d . . . . .
C7 C 0.7349(4) 0.4178(4) 0.0770(3) 0.0225(6) Uani 1 1 d . . . . .
H6 H 0.631804 0.429750 0.151606 0.034 Uiso 1 1 calc R U . . .
H8 H 0.711240 0.483996 -0.009491 0.034 Uiso 1 1 calc R U . . .
H7 H 0.852806 0.452997 0.096728 0.034 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 Cu2 2.5287(4) . ?
I1 Cu1 2.6201(4) . ?
I2 Cu2 2.5391(4) 2_756 ?
I2 Cu1 2.6257(4) . ?
I2 Cu1 2.6939(4) 2_856 ?
Cu1 S1 2.3524(7) . ?
Cu1 Cu1 2.8337(7) 2_856 ?
Cu1 Cu2 3.0489(5) 2_756 ?
Cu2 N1 2.009(2) . ?
S1 C2 1.765(3) 2_756 ?
S1 C1 1.800(3) . ?
N1 C2 1.344(3) . ?
N1 C6 1.352(3) . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C2 C3 1.396(3) . ?
C3 C4 1.388(4) . ?
C3 H9 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(4) . ?
C7 H6 0.9800 . ?
C7 H8 0.9800 . ?
C7 H7 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
Cu2 I1 Cu1 100.355(12) . . ?
Cu2 I2 Cu1 72.338(11) 2_756 . ?
Cu2 I2 Cu1 102.923(11) 2_756 2_856 ?
Cu1 I2 Cu1 64.360(13) . 2_856 ?
S1 Cu1 I1 100.29(2) . . ?
S1 Cu1 I2 115.71(2) . . ?
I1 Cu1 I2 114.470(13) . . ?
S1 Cu1 I2 100.812(19) . 2_856 ?
I1 Cu1 I2 108.034(13) . 2_856 ?
I2 Cu1 I2 115.640(13) . 2_856 ?
S1 Cu1 Cu1 125.47(2) . 2_856 ?
I1 Cu1 Cu1 132.696(19) . 2_856 ?
I2 Cu1 Cu1 58.988(12) . 2_856 ?
I2 Cu1 Cu1 56.653(12) 2_856 2_856 ?
S1 Cu1 Cu2 63.262(19) . 2_756 ?
I1 Cu1 Cu2 127.055(14) . 2_756 ?
I2 Cu1 Cu2 52.517(10) . 2_756 ?
I2 Cu1 Cu2 123.979(13) 2_856 2_756 ?
Cu1 Cu1 Cu2 88.136(17) 2_856 2_756 ?
N1 Cu2 I1 117.28(6) . . ?
N1 Cu2 I2 119.22(6) . 2_756 ?
I1 Cu2 I2 123.498(13) . 2_756 ?
N1 Cu2 Cu1 85.30(6) . 2_756 ?
I1 Cu2 Cu1 131.844(14) . 2_756 ?
I2 Cu2 Cu1 55.145(10) 2_756 2_756 ?
C2 S1 C1 103.93(14) 2_756 . ?
C2 S1 Cu1 106.14(8) 2_756 . ?
C1 S1 Cu1 105.92(10) . . ?
C2 N1 C6 119.2(2) . . ?
C2 N1 Cu2 117.15(16) . . ?
C6 N1 Cu2 123.50(18) . . ?
S1 C1 H3 109.5 . . ?
S1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
S1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C2 C3 122.9(2) . . ?
N1 C2 S1 110.90(17) . 2_756 ?
C3 C2 S1 126.1(2) . 2_756 ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H9 121.3 . . ?
C2 C3 H9 121.3 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 121.1(3) . . ?
N1 C6 C7 116.1(2) . . ?
C5 C6 C7 122.7(2) . . ?
C6 C7 H6 109.5 . . ?
C6 C7 H8 109.5 . . ?
H6 C7 H8 109.5 . . ?
C6 C7 H7 109.5 . . ?
H6 C7 H7 109.5 . . ?
H8 C7 H7 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 1.0(3) . . . . ?
Cu2 N1 C2 C3 -175.02(18) . . . . ?
C6 N1 C2 S1 177.88(17) . . . 2_756 ?
Cu2 N1 C2 S1 1.9(2) . . . 2_756 ?
N1 C2 C3 C4 0.1(4) . . . . ?
S1 C2 C3 C4 -176.35(19) 2_756 . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 N1 C6 C5 -1.5(3) . . . . ?
Cu2 N1 C6 C5 174.22(18) . . . . ?
C2 N1 C6 C7 178.3(2) . . . . ?
Cu2 N1 C6 C7 -6.0(3) . . . . ?
C4 C5 C6 N1 1.0(4) . . . . ?
C4 C5 C6 C7 -178.8(2) . . . . ?

_refine_diff_density_max         0.994
_refine_diff_density_min         -1.379
_refine_diff_density_rms         0.211

####################################################################### 
# 
# 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_c56
_database_code_depnum_ccdc_archive 'CCDC 2165802'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 Complex of Cu(I) iodide with 2-propyl-6-(methylthio)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 Cu2 I2 N2 S2'
_chemical_formula_sum            'C18 H26 Cu2 I2 N2 S2'
_chemical_formula_weight         715.41

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'
S S 0.1246 0.1234 '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                   10.0644(7)
_cell_length_b                   8.5333(7)
_cell_length_c                   14.2287(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.604(4)
_cell_angle_gamma                90
_cell_volume                     1211.25(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9137
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      29.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.482
_shelx_estimated_absorpt_T_min   0.107
_shelx_estimated_absorpt_T_max   0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4783
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21069
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3321
_reflns_number_gt                2433
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0811P)²+3.0594P] 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         3321
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_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 0.56702(4) 0.24675(4) 0.01579(3) 0.05322(17) Uani 1 1 d . . . . .
Cu1 Cu 0.38405(6) 0.03819(8) 0.02467(5) 0.04202(19) Uani 1 1 d . . . . .
S1 S 0.30605(17) -0.0077(2) 0.21950(11) 0.0657(5) Uani 1 1 d . . . . .
N1 N 0.2053(3) 0.1092(4) 0.0568(3) 0.0309(7) Uani 1 1 d . . . . .
C1 C 0.1118(4) 0.1780(5) -0.0075(3) 0.0339(9) Uani 1 1 d . . . . .
C2 C -0.0131(5) 0.2179(6) 0.0162(4) 0.0428(11) Uani 1 1 d . . . . .
H6 H -0.076991 0.263067 -0.028949 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0425(5) 0.1907(7) 0.1067(4) 0.0449(11) Uani 1 1 d . . . . .
H1 H -0.126119 0.217764 0.122687 0.054 Uiso 1 1 calc R U . . .
C4 C 0.0520(5) 0.1235(7) 0.1732(4) 0.0429(11) Uani 1 1 d . . . . .
H5 H 0.034295 0.105385 0.234783 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1750(4) 0.0836(6) 0.1453(3) 0.0360(9) Uani 1 1 d . . . . .
C6 C 0.2456(7) -0.0137(9) 0.3327(4) 0.0650(18) Uani 1 1 d . . . . .
H2 H 0.218692 0.089525 0.349238 0.098 Uiso 1 1 calc R U . . .
H4 H 0.315645 -0.050464 0.379991 0.098 Uiso 1 1 calc R U . . .
H3 H 0.170282 -0.083398 0.329478 0.098 Uiso 1 1 calc R U . . .
C7 C 0.1504(6) 0.2157(6) -0.1029(4) 0.0419(11) Uani 1 1 d . . . . .
H12 H 0.075704 0.192680 -0.151336 0.050 Uiso 1 1 calc R U . . .
H13 H 0.225223 0.150041 -0.114549 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1896(7) 0.3875(7) -0.1099(4) 0.0559(14) Uani 1 1 d . . . . .
H11 H 0.114328 0.452697 -0.098595 0.067 Uiso 1 1 calc R U . . .
H7 H 0.263418 0.410366 -0.060834 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2306(10) 0.4291(10) -0.2057(5) 0.084(2) Uani 1 1 d . . . . .
H10 H 0.317349 0.385660 -0.210614 0.126 Uiso 1 1 calc R U . . .
H9 H 0.233994 0.541023 -0.211945 0.126 Uiso 1 1 calc R U . . .
H8 H 0.166291 0.387027 -0.255110 0.126 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 2.5614(8) 3_655 ?
I1 Cu1 2.5760(7) . ?
Cu1 N1 2.007(3) . ?
Cu1 Cu1 2.6074(11) 3_655 ?
S1 C5 1.759(5) . ?
S1 C6 1.796(6) . ?
N1 C5 1.352(6) . ?
N1 C1 1.357(6) . ?
C1 C2 1.387(7) . ?
C1 C7 1.496(7) . ?
C2 C3 1.378(8) . ?
C2 H6 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H1 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H5 0.9300 . ?
C6 H2 0.9600 . ?
C6 H4 0.9600 . ?
C6 H3 0.9600 . ?
C7 C8 1.525(8) . ?
C7 H12 0.9700 . ?
C7 H13 0.9700 . ?
C8 C9 1.517(8) . ?
C8 H11 0.9700 . ?
C8 H7 0.9700 . ?
C9 H10 0.9600 . ?
C9 H9 0.9600 . ?
C9 H8 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu1 61.00(2) 3_655 . ?
N1 Cu1 I1 122.84(11) . 3_655 ?
N1 Cu1 I1 118.08(11) . . ?
I1 Cu1 I1 119.00(2) 3_655 . ?
N1 Cu1 Cu1 176.21(11) . 3_655 ?
I1 Cu1 Cu1 59.78(3) 3_655 3_655 ?
I1 Cu1 Cu1 59.23(3) . 3_655 ?
C5 S1 C6 103.6(3) . . ?
C5 N1 C1 118.5(4) . . ?
C5 N1 Cu1 118.9(3) . . ?
C1 N1 Cu1 122.6(3) . . ?
N1 C1 C2 120.8(4) . . ?
N1 C1 C7 117.8(4) . . ?
C2 C1 C7 121.4(4) . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H6 120.0 . . ?
C1 C2 H6 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H1 120.0 . . ?
C2 C3 H1 120.0 . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 H5 121.1 . . ?
C5 C4 H5 121.1 . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 S1 112.8(3) . . ?
C4 C5 S1 124.2(4) . . ?
S1 C6 H2 109.5 . . ?
S1 C6 H4 109.5 . . ?
H2 C6 H4 109.5 . . ?
S1 C6 H3 109.5 . . ?
H2 C6 H3 109.5 . . ?
H4 C6 H3 109.5 . . ?
C1 C7 C8 111.5(4) . . ?
C1 C7 H12 109.3 . . ?
C8 C7 H12 109.3 . . ?
C1 C7 H13 109.3 . . ?
C8 C7 H13 109.3 . . ?
H12 C7 H13 108.0 . . ?
C9 C8 C7 112.8(5) . . ?
C9 C8 H11 109.0 . . ?
C7 C8 H11 109.0 . . ?
C9 C8 H7 109.0 . . ?
C7 C8 H7 109.0 . . ?
H11 C8 H7 107.8 . . ?
C8 C9 H10 109.5 . . ?
C8 C9 H9 109.5 . . ?
H10 C9 H9 109.5 . . ?
C8 C9 H8 109.5 . . ?
H10 C9 H8 109.5 . . ?
H9 C9 H8 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.5(6) . . . . ?
Cu1 N1 C1 C2 176.6(4) . . . . ?
C5 N1 C1 C7 175.8(4) . . . . ?
Cu1 N1 C1 C7 -6.1(6) . . . . ?
N1 C1 C2 C3 1.3(7) . . . . ?
C7 C1 C2 C3 -175.8(5) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C1 N1 C5 C4 0.5(7) . . . . ?
Cu1 N1 C5 C4 -177.7(4) . . . . ?
C1 N1 C5 S1 179.5(3) . . . . ?
Cu1 N1 C5 S1 1.3(5) . . . . ?
C3 C4 C5 N1 0.6(8) . . . . ?
C3 C4 C5 S1 -178.3(4) . . . . ?
C6 S1 C5 N1 175.7(4) . . . . ?
C6 S1 C5 C4 -5.3(6) . . . . ?
N1 C1 C7 C8 -98.9(6) . . . . ?
C2 C1 C7 C8 78.3(6) . . . . ?
C1 C7 C8 C9 179.4(6) . . . . ?

_refine_diff_density_max         1.536
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.172

####################################################################### 
# 
# 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_c53
_database_code_depnum_ccdc_archive 'CCDC 2165801'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 Complex of Cu(I) iodide with 2-methyl-6-(benzylthio)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 Cu2 I2 N2 S2'
_chemical_formula_sum            'C26 H26 Cu2 I2 N2 S2'
_chemical_formula_weight         811.49

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'
S S 0.1246 0.1234 '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                   11.5255(9)
_cell_length_b                   10.2674(7)
_cell_length_c                   12.1602(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.018(3)
_cell_angle_gamma                90
_cell_volume                     1428.22(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    3.814
_shelx_estimated_absorpt_T_min   0.150
_shelx_estimated_absorpt_T_max   0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1725
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27893
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         30.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3976
_reflns_number_gt                2879
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0518P)²+8.5931P] 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         3976
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 -0.03484(4) 0.56655(4) 0.82746(4) 0.05528(16) Uani 1 1 d . . . . .
Cu1 Cu 0.02451(6) 0.38109(7) 0.96511(7) 0.0482(2) Uani 1 1 d . . . . .
S1 S 0.26131(15) 0.24100(17) 0.99140(18) 0.0620(5) Uani 1 1 d . . . . .
N1 N 0.0446(4) 0.1972(5) 0.9142(4) 0.0446(11) Uani 1 1 d . . . . .
C1 C -0.0481(6) 0.1278(7) 0.8691(6) 0.0561(16) Uani 1 1 d . . . . .
C2 C -0.0350(7) -0.0021(8) 0.8395(6) 0.067(2) Uani 1 1 d . . . . .
H10 H -0.099390 -0.049059 0.807362 0.080 Uiso 1 1 calc R U . . .
C3 C 0.0715(8) -0.0603(7) 0.8573(7) 0.070(2) Uani 1 1 d . . . . .
H9 H 0.079802 -0.147383 0.838589 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1663(7) 0.0093(7) 0.9028(7) 0.0625(18) Uani 1 1 d . . . . .
H8 H 0.239901 -0.028965 0.914831 0.075 Uiso 1 1 calc R U . . .
C5 C 0.1504(5) 0.1385(6) 0.9305(5) 0.0456(13) Uani 1 1 d . . . . .
C6 C 0.3926(7) 0.1471(7) 0.9781(8) 0.067(2) Uani 1 1 d . . . . .
H6 H 0.395184 0.070446 1.024928 0.081 Uiso 1 1 calc R U . . .
H7 H 0.393052 0.119051 0.901956 0.081 Uiso 1 1 calc R U . . .
C7 C 0.4966(6) 0.2327(7) 1.0127(5) 0.0504(14) Uani 1 1 d . . . . .
C8 C 0.5614(8) 0.2193(8) 1.1152(6) 0.069(2) Uani 1 1 d . . . . .
H5 H 0.540721 0.157410 1.165237 0.083 Uiso 1 1 calc R U . . .
C9 C 0.6599(8) 0.3009(11) 1.1435(8) 0.084(3) Uani 1 1 d . . . . .
H4 H 0.705387 0.292473 1.211743 0.101 Uiso 1 1 calc R U . . .
C10 C 0.6863(8) 0.3907(10) 1.0699(9) 0.084(3) Uani 1 1 d . . . . .
H3 H 0.749727 0.445692 1.088829 0.101 Uiso 1 1 calc R U . . .
C11 C 0.6236(8) 0.4031(10) 0.9702(9) 0.086(3) Uani 1 1 d . . . . .
H2 H 0.644411 0.465227 0.920535 0.103 Uiso 1 1 calc R U . . .
C12 C 0.5302(7) 0.3255(9) 0.9419(7) 0.069(2) Uani 1 1 d . . . . .
H1 H 0.487476 0.335169 0.872427 0.083 Uiso 1 1 calc R U . . .
C13 C -0.1627(7) 0.1961(9) 0.8529(8) 0.077(2) Uani 1 1 d . . . . .
H11 H -0.166177 0.251073 0.788648 0.115 Uiso 1 1 calc R U . . .
H12 H -0.171298 0.248325 0.916862 0.115 Uiso 1 1 calc R U . . .
H13 H -0.224636 0.133138 0.842543 0.115 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 2.5675(9) 3_567 ?
I1 Cu1 2.5721(9) . ?
Cu1 N1 2.009(5) . ?
Cu1 Cu1 2.6680(15) 3_567 ?
S1 C5 1.749(6) . ?
S1 C6 1.818(7) . ?
N1 C1 1.344(8) . ?
N1 C5 1.352(8) . ?
C1 C2 1.394(11) . ?
C1 C13 1.488(11) . ?
C2 C3 1.359(12) . ?
C2 H10 0.9300 . ?
C3 C4 1.365(11) . ?
C3 H9 0.9300 . ?
C4 C5 1.386(9) . ?
C4 H8 0.9300 . ?
C6 C7 1.504(10) . ?
C6 H6 0.9700 . ?
C6 H7 0.9700 . ?
C7 C12 1.371(10) . ?
C7 C8 1.380(11) . ?
C8 C9 1.419(13) . ?
C8 H5 0.9300 . ?
C9 C10 1.345(14) . ?
C9 H4 0.9300 . ?
C10 C11 1.339(14) . ?
C10 H3 0.9300 . ?
C11 C12 1.350(12) . ?
C11 H2 0.9300 . ?
C12 H1 0.9300 . ?
C13 H11 0.9600 . ?
C13 H12 0.9600 . ?
C13 H13 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu1 62.54(3) 3_567 . ?
N1 Cu1 I1 120.42(15) . 3_567 ?
N1 Cu1 I1 121.77(15) . . ?
I1 Cu1 I1 117.46(3) 3_567 . ?
N1 Cu1 Cu1 174.21(15) . 3_567 ?
I1 Cu1 Cu1 58.81(3) 3_567 3_567 ?
I1 Cu1 Cu1 58.64(3) . 3_567 ?
C5 S1 C6 102.5(3) . . ?
C1 N1 C5 118.7(6) . . ?
C1 N1 Cu1 120.6(5) . . ?
C5 N1 Cu1 120.6(4) . . ?
N1 C1 C2 120.5(7) . . ?
N1 C1 C13 116.9(6) . . ?
C2 C1 C13 122.6(7) . . ?
C3 C2 C1 120.2(7) . . ?
C3 C2 H10 119.9 . . ?
C1 C2 H10 119.9 . . ?
C2 C3 C4 119.8(7) . . ?
C2 C3 H9 120.1 . . ?
C4 C3 H9 120.1 . . ?
C3 C4 C5 118.5(7) . . ?
C3 C4 H8 120.8 . . ?
C5 C4 H8 120.8 . . ?
N1 C5 C4 122.3(6) . . ?
N1 C5 S1 113.1(4) . . ?
C4 C5 S1 124.5(5) . . ?
C7 C6 S1 108.0(5) . . ?
C7 C6 H6 110.1 . . ?
S1 C6 H6 110.1 . . ?
C7 C6 H7 110.1 . . ?
S1 C6 H7 110.1 . . ?
H6 C6 H7 108.4 . . ?
C12 C7 C8 118.3(7) . . ?
C12 C7 C6 120.5(7) . . ?
C8 C7 C6 121.3(7) . . ?
C7 C8 C9 119.2(8) . . ?
C7 C8 H5 120.4 . . ?
C9 C8 H5 120.4 . . ?
C10 C9 C8 118.9(8) . . ?
C10 C9 H4 120.6 . . ?
C8 C9 H4 120.6 . . ?
C11 C10 C9 121.7(9) . . ?
C11 C10 H3 119.1 . . ?
C9 C10 H3 119.1 . . ?
C10 C11 C12 120.0(10) . . ?
C10 C11 H2 120.0 . . ?
C12 C11 H2 120.0 . . ?
C11 C12 C7 121.9(8) . . ?
C11 C12 H1 119.1 . . ?
C7 C12 H1 119.1 . . ?
C1 C13 H11 109.5 . . ?
C1 C13 H12 109.5 . . ?
H11 C13 H12 109.5 . . ?
C1 C13 H13 109.5 . . ?
H11 C13 H13 109.5 . . ?
H12 C13 H13 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.3(9) . . . . ?
Cu1 N1 C1 C2 -176.4(5) . . . . ?
C5 N1 C1 C13 179.9(6) . . . . ?
Cu1 N1 C1 C13 3.7(9) . . . . ?
N1 C1 C2 C3 0.9(11) . . . . ?
C13 C1 C2 C3 -179.2(8) . . . . ?
C1 C2 C3 C4 -1.1(12) . . . . ?
C2 C3 C4 C5 0.6(12) . . . . ?
C1 N1 C5 C4 -0.2(9) . . . . ?
Cu1 N1 C5 C4 176.0(5) . . . . ?
C1 N1 C5 S1 -179.2(5) . . . . ?
Cu1 N1 C5 S1 -3.0(6) . . . . ?
C3 C4 C5 N1 0.0(11) . . . . ?
C3 C4 C5 S1 178.9(6) . . . . ?
C6 S1 C5 N1 -169.6(5) . . . . ?
C6 S1 C5 C4 11.4(7) . . . . ?
C5 S1 C6 C7 171.9(5) . . . . ?
S1 C6 C7 C12 -78.3(8) . . . . ?
S1 C6 C7 C8 102.5(7) . . . . ?
C12 C7 C8 C9 -0.2(11) . . . . ?
C6 C7 C8 C9 179.0(7) . . . . ?
C7 C8 C9 C10 1.0(12) . . . . ?
C8 C9 C10 C11 -1.4(14) . . . . ?
C9 C10 C11 C12 0.9(15) . . . . ?
C10 C11 C12 C7 0.0(15) . . . . ?
C8 C7 C12 C11 -0.3(12) . . . . ?
C6 C7 C12 C11 -179.5(8) . . . . ?

_refine_diff_density_max         1.938
_refine_diff_density_min         -2.104
_refine_diff_density_rms         0.154

