#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:07:18 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286158 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/25/7062558.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062558
loop_
_publ_author_name
'Mandal, Suman'
'Harijan, Dinesh'
'Muduli, Gopendra'
'Subramaniyam, Kalaivanan'
'Rengan, Aravind Kumar'
'Prabusankar, Ganesan'
_publ_section_title
;
 Highly active higher coordinated copper(i)--N-heterocyclic chalcogenone
 catalysed click chemistry
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15027
_journal_page_last               15035
_journal_paper_doi               10.1039/D3NJ01875J
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C42 H40 Cu I N4 S2'
_chemical_formula_sum            'C42 H40 Cu I N4 S2'
_chemical_formula_weight         855.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-30 deposited with the CCDC.	2023-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.508(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.154(6)
_cell_length_b                   10.252(2)
_cell_length_c                   14.169(3)
_cell_measurement_reflns_used    9797
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.274
_cell_measurement_theta_min      2.85
_cell_volume                     3721.2(14)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35507
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.334
_diffrn_reflns_theta_min         2.140
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_T_max  0.7414
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0874 after correction.
The Ratio of minimum to maximum transmission is 0.8990.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       prism
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0274P)²+3.5373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3824
_reflns_number_total             4179
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01875j2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7062555--7062561.cif.'
_cod_original_cell_volume        3721.0(14)
_cod_database_code               7062558
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.777
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.500000 0.48368(2) 0.250000 0.04901(8) Uani 1 2 d S T P . .
Cu1 Cu 0.500000 0.23207(4) 0.250000 0.04343(10) Uani 1 2 d S T P . .
S1 S 0.43027(2) 0.13357(4) 0.25844(4) 0.03926(12) Uani 1 1 d . . . . .
C1 C 0.41530(6) 0.25192(17) 0.32750(14) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.38263(6) 0.35395(14) 0.28829(12) 0.0348(3) Uani 1 1 d . . . . .
N2 N 0.43388(6) 0.26158(16) 0.43172(12) 0.0385(3) Uani 1 1 d . . . . .
C2 C 0.38193(8) 0.4288(2) 0.36859(16) 0.0455(5) Uani 1 1 d . . . . .
H2 H 0.362833 0.504882 0.362216 0.055 Uiso 1 1 calc R U . . .
C3 C 0.41378(9) 0.3719(2) 0.45735(17) 0.0485(5) Uani 1 1 d . . . . .
H3 H 0.421031 0.401353 0.524010 0.058 Uiso 1 1 calc R U . . .
C19 C 0.47318(8) 0.1731(2) 0.50641(17) 0.0473(5) Uani 1 1 d . . . . .
H19 H 0.472818 0.091281 0.470395 0.057 Uiso 1 1 calc R U . . .
C21 C 0.45968(11) 0.1422(2) 0.5967(2) 0.0609(6) Uani 1 1 d . . . . .
H21A H 0.423633 0.117193 0.571126 0.091 Uiso 1 1 calc R U . . .
H21B H 0.465604 0.217849 0.640065 0.091 Uiso 1 1 calc R U . . .
H21C H 0.481232 0.071779 0.636398 0.091 Uiso 1 1 calc R U . . .
C20 C 0.52654(10) 0.2334(4) 0.5399(2) 0.0759(8) Uani 1 1 d . . . . .
H20A H 0.533489 0.249435 0.480087 0.114 Uiso 1 1 calc R U . . .
H20B H 0.552389 0.174911 0.586036 0.114 Uiso 1 1 calc R U . . .
H20C H 0.527737 0.314285 0.575006 0.114 Uiso 1 1 calc R U . . .
C4 C 0.35629(7) 0.3861(2) 0.17687(14) 0.0370(4) Uani 1 1 d . . . . .
H4A H 0.349021 0.306192 0.136658 0.044 Uiso 1 1 calc R U . . .
H4B H 0.379391 0.438940 0.157437 0.044 Uiso 1 1 calc R U . . .
C5 C 0.30578(7) 0.45923(19) 0.15127(14) 0.0356(4) Uani 1 1 d . . . . .
C6 C 0.25928(7) 0.38882(19) 0.12628(14) 0.0355(4) Uani 1 1 d . . . . .
C7 C 0.25710(8) 0.2495(2) 0.12597(17) 0.0456(5) Uani 1 1 d . . . . .
H7 H 0.287903 0.202188 0.145487 0.055 Uiso 1 1 calc R U . . .
C8 C 0.21138(10) 0.1847(2) 0.09800(19) 0.0542(5) Uani 1 1 d . . . . .
H8 H 0.211308 0.093957 0.098667 0.065 Uiso 1 1 calc R U . . .
C9 C 0.16386(9) 0.2530(3) 0.06786(19) 0.0573(6) Uani 1 1 d . . . . .
H9 H 0.132637 0.207336 0.047702 0.069 Uiso 1 1 calc R U . . .
C10 C 0.16374(9) 0.3842(3) 0.06830(19) 0.0537(5) Uani 1 1 d . . . . .
H10 H 0.132184 0.428210 0.048446 0.064 Uiso 1 1 calc R U . . .
C11 C 0.21092(8) 0.4574(2) 0.09855(15) 0.0411(4) Uani 1 1 d . . . . .
C12 C 0.21136(8) 0.5931(2) 0.10081(16) 0.0458(5) Uani 1 1 d . . . . .
H12 H 0.180050 0.637418 0.083701 0.055 Uiso 1 1 calc R U . . .
C13 C 0.25703(8) 0.6643(2) 0.12778(15) 0.0418(4) Uani 1 1 d . . . . .
C14 C 0.25724(10) 0.8034(2) 0.13160(19) 0.0548(5) Uani 1 1 d . . . . .
H14 H 0.225966 0.847598 0.115281 0.066 Uiso 1 1 calc R U . . .
C15 C 0.30151(12) 0.8719(2) 0.1582(2) 0.0618(6) Uani 1 1 d . . . . .
H15 H 0.300667 0.962545 0.160155 0.074 Uiso 1 1 calc R U . . .
C16 C 0.34946(10) 0.8066(2) 0.18327(19) 0.0568(6) Uani 1 1 d . . . . .
H16 H 0.379992 0.854921 0.202099 0.068 Uiso 1 1 calc R U . . .
C17 C 0.35160(9) 0.6750(2) 0.18029(17) 0.0469(5) Uani 1 1 d . . . . .
H17 H 0.383573 0.634464 0.196371 0.056 Uiso 1 1 calc R U . . .
C18 C 0.30558(7) 0.59653(19) 0.15283(14) 0.0363(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
S1 Cu1 I1 116.610(16) . . ?
S1 Cu1 I1 116.610(16) 2_655 . ?
S1 Cu1 S1 126.78(3) . 2_655 ?
C1 S1 Cu1 97.97(6) . . ?
N1 C1 S1 126.79(14) . . ?
N2 C1 S1 126.84(14) . . ?
N2 C1 N1 106.36(15) . . ?
C1 N1 C2 109.39(16) . . ?
C1 N1 C4 124.54(15) . . ?
C2 N1 C4 125.80(15) . . ?
C1 N2 C3 109.45(16) . . ?
C1 N2 C19 124.89(16) . . ?
C3 N2 C19 125.47(17) . . ?
N1 C2 H2 126.3 . . ?
C3 C2 N1 107.41(17) . . ?
C3 C2 H2 126.3 . . ?
N2 C3 H3 126.3 . . ?
C2 C3 N2 107.36(18) . . ?
C2 C3 H3 126.3 . . ?
N2 C19 H19 108.0 . . ?
N2 C19 C21 110.96(18) . . ?
N2 C19 C20 109.0(2) . . ?
C21 C19 H19 108.0 . . ?
C20 C19 H19 108.0 . . ?
C20 C19 C21 112.8(2) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
N1 C4 C5 111.87(15) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C6 C5 C4 119.38(17) . . ?
C6 C5 C18 120.52(16) . . ?
C18 C5 C4 120.10(17) . . ?
C5 C6 C7 123.23(18) . . ?
C5 C6 C11 119.74(18) . . ?
C7 C6 C11 117.03(18) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 118.9(2) . . ?
C12 C11 C6 119.05(18) . . ?
C12 C11 C10 122.06(19) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 122.07(18) . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 121.7(2) . . ?
C12 C13 C18 119.34(18) . . ?
C14 C13 C18 119.0(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C5 C18 C13 119.23(17) . . ?
C5 C18 C17 123.76(18) . . ?
C17 C18 C13 117.00(19) . . ?
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 2.5793(7) . ?
Cu1 S1 2.2544(6) . ?
Cu1 S1 2.2545(6) 2_655 ?
S1 C1 1.7174(18) . ?
C1 N1 1.351(2) . ?
C1 N2 1.350(2) . ?
N1 C2 1.379(2) . ?
N1 C4 1.476(2) . ?
N2 C3 1.379(2) . ?
N2 C19 1.481(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.338(3) . ?
C3 H3 0.9300 . ?
C19 H19 0.9800 . ?
C19 C21 1.512(3) . ?
C19 C20 1.507(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.512(3) . ?
C5 C6 1.406(3) . ?
C5 C18 1.408(3) . ?
C6 C7 1.429(3) . ?
C6 C11 1.435(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.354(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.345(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.428(3) . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(3) . ?
C13 C14 1.427(3) . ?
C13 C18 1.441(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.341(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.414(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.352(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.435(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C1 N1 90.55(16) . . . . ?
Cu1 S1 C1 N2 -89.36(16) . . . . ?
S1 C1 N1 C2 -178.51(15) . . . . ?
S1 C1 N1 C4 -4.2(3) . . . . ?
S1 C1 N2 C3 178.31(16) . . . . ?
S1 C1 N2 C19 3.0(3) . . . . ?
C1 N1 C2 C3 -0.7(2) . . . . ?
C1 N1 C4 C5 153.36(17) . . . . ?
C1 N2 C3 C2 1.2(3) . . . . ?
C1 N2 C19 C21 -139.9(2) . . . . ?
C1 N2 C19 C20 95.3(2) . . . . ?
N1 C1 N2 C3 -1.6(2) . . . . ?
N1 C1 N2 C19 -176.90(18) . . . . ?
N1 C2 C3 N2 -0.3(3) . . . . ?
N1 C4 C5 C6 -88.2(2) . . . . ?
N1 C4 C5 C18 91.7(2) . . . . ?
N2 C1 N1 C2 1.4(2) . . . . ?
N2 C1 N1 C4 175.76(16) . . . . ?
C2 N1 C4 C5 -33.2(3) . . . . ?
C3 N2 C19 C21 45.5(3) . . . . ?
C3 N2 C19 C20 -79.2(3) . . . . ?
C19 N2 C3 C2 176.5(2) . . . . ?
C4 N1 C2 C3 -174.93(19) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C4 C5 C6 C11 -177.95(17) . . . . ?
C4 C5 C18 C13 179.74(16) . . . . ?
C4 C5 C18 C17 -1.6(3) . . . . ?
C5 C6 C7 C8 -177.7(2) . . . . ?
C5 C6 C11 C10 176.84(19) . . . . ?
C5 C6 C11 C12 -2.4(3) . . . . ?
C6 C5 C18 C13 -0.4(3) . . . . ?
C6 C5 C18 C17 178.24(18) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C11 C12 C13 0.8(3) . . . . ?
C7 C6 C11 C10 -2.6(3) . . . . ?
C7 C6 C11 C12 178.08(18) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C6 1.7(3) . . . . ?
C9 C10 C11 C12 -179.0(2) . . . . ?
C10 C11 C12 C13 -178.4(2) . . . . ?
C11 C6 C7 C8 1.8(3) . . . . ?
C11 C12 C13 C14 -178.9(2) . . . . ?
C11 C12 C13 C18 1.0(3) . . . . ?
C12 C13 C14 C15 179.7(2) . . . . ?
C12 C13 C18 C5 -1.2(3) . . . . ?
C12 C13 C18 C17 -179.93(19) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C13 C18 C5 178.71(18) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C5 -178.2(2) . . . . ?
C16 C17 C18 C13 0.5(3) . . . . ?
C18 C5 C6 C7 -178.32(18) . . . . ?
C18 C5 C6 C11 2.2(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
