#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:07:18 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286158 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062557.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_7062557
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 Se2'
_chemical_formula_sum            'C42 H40 Cu I N4 Se2'
_chemical_formula_weight         949.14
_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             2022-12-26
_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                 115.236(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1758(15)
_cell_length_b                   10.3689(4)
_cell_length_c                   14.2314(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.030
_cell_measurement_theta_min      2.434
_cell_volume                     3760.9(3)
_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 0.999
_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  0.0476
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       -18
_diffrn_reflns_number            42344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_min         2.120
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.373
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8227.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_description       plate
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0241
_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)+(0.0210P)²+3.7595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3488
_reflns_number_total             4162
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01875j2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7062555--7062561.cif.'
_cod_database_code               7062557
_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   0.688
_shelx_estimated_absorpt_t_min   0.474
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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 0.47496(2) 0.250000 0.05003(8) Uani 1 2 d S T P . .
Se1 Se 0.42737(2) 0.12023(2) 0.25634(2) 0.04095(7) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.22768(4) 0.250000 0.04530(11) Uani 1 2 d S T P . .
C1 C 0.41283(8) 0.2521(2) 0.32959(17) 0.0335(5) Uani 1 1 d . . . . .
N2 N 0.38114(7) 0.35410(16) 0.28875(14) 0.0348(4) Uani 1 1 d . . . . .
N3 N 0.43245(7) 0.26453(17) 0.43372(14) 0.0389(4) Uani 1 1 d . . . . .
C7 C 0.35411(8) 0.3837(2) 0.17697(16) 0.0371(5) Uani 1 1 d . . . . .
H7A H 0.347001 0.303942 0.137671 0.045 Uiso 1 1 calc R U . . .
H7B H 0.376889 0.435965 0.157076 0.045 Uiso 1 1 calc R U . . .
C8 C 0.30315(8) 0.4547(2) 0.15023(16) 0.0349(5) Uani 1 1 d . . . . .
C9 C 0.30233(9) 0.5905(2) 0.15084(16) 0.0369(5) Uani 1 1 d . . . . .
C10 C 0.34804(10) 0.6685(2) 0.17760(19) 0.0468(6) Uani 1 1 d . . . . .
H10 H 0.380251 0.629147 0.193799 0.056 Uiso 1 1 calc R U . . .
C11 C 0.34530(11) 0.7985(3) 0.1798(2) 0.0562(7) Uani 1 1 d . . . . .
H11 H 0.375748 0.846834 0.198005 0.067 Uiso 1 1 calc R U . . .
C12 C 0.29743(13) 0.8623(3) 0.1552(2) 0.0612(7) Uani 1 1 d . . . . .
H12 H 0.296379 0.951868 0.156946 0.073 Uiso 1 1 calc R U . . .
C13 C 0.25307(11) 0.7933(2) 0.1289(2) 0.0539(6) Uani 1 1 d . . . . .
H13 H 0.221532 0.836196 0.112466 0.065 Uiso 1 1 calc R U . . .
C14 C 0.25349(9) 0.6557(2) 0.12591(17) 0.0406(5) Uani 1 1 d . . . . .
C15 C 0.20826(9) 0.5844(2) 0.09980(18) 0.0452(6) Uani 1 1 d . . . . .
H15 H 0.176763 0.627507 0.083297 0.054 Uiso 1 1 calc R U . . .
C16 C 0.20814(8) 0.4501(2) 0.09732(17) 0.0403(5) Uani 1 1 d . . . . .
C17 C 0.16114(10) 0.3775(3) 0.0673(2) 0.0537(7) Uani 1 1 d . . . . .
H17 H 0.129381 0.420302 0.048325 0.064 Uiso 1 1 calc R U . . .
C18 C 0.16186(10) 0.2480(3) 0.0660(2) 0.0572(7) Uani 1 1 d . . . . .
H18 H 0.130633 0.202163 0.045009 0.069 Uiso 1 1 calc R U . . .
C19 C 0.20936(10) 0.1814(3) 0.0959(2) 0.0538(6) Uani 1 1 d . . . . .
H19 H 0.209408 0.091754 0.096164 0.065 Uiso 1 1 calc R U . . .
C20 C 0.25534(10) 0.2461(2) 0.12461(18) 0.0449(6) Uani 1 1 d . . . . .
H20 H 0.286398 0.199901 0.144259 0.054 Uiso 1 1 calc R U . . .
C21 C 0.25686(8) 0.3834(2) 0.12515(16) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.38220(9) 0.4319(2) 0.36798(18) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.363941 0.508801 0.360374 0.055 Uiso 1 1 calc R U . . .
C3 C 0.41416(10) 0.3771(2) 0.45780(19) 0.0493(6) Uani 1 1 d . . . . .
H3 H 0.422473 0.409032 0.524055 0.059 Uiso 1 1 calc R U . . .
C4 C 0.47148(9) 0.1773(2) 0.51035(19) 0.0475(6) Uani 1 1 d . . . . .
H4 H 0.470775 0.095476 0.475365 0.057 Uiso 1 1 calc R U . . .
C5 C 0.45751(12) 0.1497(3) 0.5994(2) 0.0625(7) Uani 1 1 d . . . . .
H5A H 0.421582 0.122340 0.572770 0.094 Uiso 1 1 calc R U . . .
H5B H 0.462171 0.226419 0.640201 0.094 Uiso 1 1 calc R U . . .
H5C H 0.479869 0.082733 0.642105 0.094 Uiso 1 1 calc R U . . .
C6 C 0.52529(10) 0.2343(4) 0.5451(3) 0.0771(10) Uani 1 1 d . . . . .
H6A H 0.532320 0.249435 0.485637 0.116 Uiso 1 1 calc R U . . .
H6B H 0.550876 0.175447 0.591433 0.116 Uiso 1 1 calc R U . . .
H6C H 0.527105 0.314353 0.580280 0.116 Uiso 1 1 calc R U . . .
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'
Se Se -0.0929 2.2259 '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
C1 Se1 Cu1 94.34(6) . . ?
Se1 Cu1 I1 118.100(10) 2_655 . ?
Se1 Cu1 I1 118.100(10) . . ?
Se1 Cu1 Se1 123.80(2) . 2_655 ?
N2 C1 Se1 126.67(16) . . ?
N2 C1 N3 106.54(18) . . ?
N3 C1 Se1 126.78(15) . . ?
C1 N2 C7 124.89(18) . . ?
C1 N2 C2 109.15(18) . . ?
C2 N2 C7 125.68(18) . . ?
C1 N3 C3 109.46(18) . . ?
C1 N3 C4 125.32(18) . . ?
C3 N3 C4 124.99(19) . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
N2 C7 C8 111.81(17) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C9 C8 C7 120.15(19) . . ?
C21 C8 C7 119.10(19) . . ?
C21 C8 C9 120.75(19) . . ?
C8 C9 C10 123.5(2) . . ?
C8 C9 C14 119.1(2) . . ?
C10 C9 C14 117.4(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 118.8(2) . . ?
C15 C14 C9 119.5(2) . . ?
C15 C14 C13 121.7(2) . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.3(2) . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C17 121.9(2) . . ?
C15 C16 C21 118.9(2) . . ?
C17 C16 C21 119.1(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C8 C21 C16 119.4(2) . . ?
C8 C21 C20 123.3(2) . . ?
C20 C21 C16 117.2(2) . . ?
N2 C2 H2 126.1 . . ?
C3 C2 N2 107.8(2) . . ?
C3 C2 H2 126.1 . . ?
N3 C3 H3 126.5 . . ?
C2 C3 N3 107.0(2) . . ?
C2 C3 H3 126.5 . . ?
N3 C4 H4 107.9 . . ?
N3 C4 C5 110.9(2) . . ?
N3 C4 C6 109.3(2) . . ?
C5 C4 H4 107.9 . . ?
C6 C4 H4 107.9 . . ?
C6 C4 C5 112.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 2.5641(5) . ?
Se1 Cu1 2.3654(3) . ?
Se1 C1 1.867(2) . ?
C1 N2 1.346(3) . ?
C1 N3 1.349(3) . ?
N2 C7 1.474(3) . ?
N2 C2 1.376(3) . ?
N3 C3 1.377(3) . ?
N3 C4 1.481(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(3) . ?
C8 C9 1.408(3) . ?
C8 C21 1.407(3) . ?
C9 C10 1.428(3) . ?
C9 C14 1.435(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.351(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.406(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.347(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.428(3) . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(3) . ?
C16 C17 1.422(3) . ?
C16 C21 1.434(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.343(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.401(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.424(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.336(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9800 . ?
C4 C5 1.507(4) . ?
C4 C6 1.501(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
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
Se1 C1 N2 C7 -3.5(3) . . . . ?
Se1 C1 N2 C2 -177.80(17) . . . . ?
Se1 C1 N3 C3 177.44(17) . . . . ?
Se1 C1 N3 C4 2.7(3) . . . . ?
Cu1 Se1 C1 N2 89.54(18) . . . . ?
Cu1 Se1 C1 N3 -89.68(18) . . . . ?
C1 N2 C7 C8 150.6(2) . . . . ?
C1 N2 C2 C3 -0.6(3) . . . . ?
C1 N3 C3 C2 1.6(3) . . . . ?
C1 N3 C4 C5 -138.2(2) . . . . ?
C1 N3 C4 C6 96.8(3) . . . . ?
N2 C1 N3 C3 -1.9(2) . . . . ?
N2 C1 N3 C4 -176.6(2) . . . . ?
N2 C7 C8 C9 91.2(2) . . . . ?
N2 C7 C8 C21 -88.6(2) . . . . ?
N2 C2 C3 N3 -0.6(3) . . . . ?
N3 C1 N2 C7 175.81(19) . . . . ?
N3 C1 N2 C2 1.6(2) . . . . ?
C7 N2 C2 C3 -174.8(2) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C7 C8 C9 C14 -179.54(19) . . . . ?
C7 C8 C21 C16 -178.54(19) . . . . ?
C7 C8 C21 C20 0.7(3) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C8 C9 C14 C13 178.6(2) . . . . ?
C8 C9 C14 C15 -1.3(3) . . . . ?
C9 C8 C21 C16 1.6(3) . . . . ?
C9 C8 C21 C20 -179.1(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C9 C14 C15 C16 0.4(4) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C9 C14 C15 -179.9(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C12 C13 C14 C15 179.6(3) . . . . ?
C13 C14 C15 C16 -179.5(2) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C14 C15 C16 C17 -178.1(2) . . . . ?
C14 C15 C16 C21 1.5(3) . . . . ?
C15 C16 C17 C18 -179.6(3) . . . . ?
C15 C16 C21 C8 -2.5(3) . . . . ?
C15 C16 C21 C20 178.2(2) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C17 C16 C21 C8 177.1(2) . . . . ?
C17 C16 C21 C20 -2.3(3) . . . . ?
C17 C18 C19 C20 -1.5(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 C8 -177.4(2) . . . . ?
C19 C20 C21 C16 1.9(3) . . . . ?
C21 C8 C9 C10 178.7(2) . . . . ?
C21 C8 C9 C14 0.3(3) . . . . ?
C21 C16 C17 C18 0.8(4) . . . . ?
C2 N2 C7 C8 -36.1(3) . . . . ?
C3 N3 C4 C5 47.9(3) . . . . ?
C3 N3 C4 C6 -77.1(3) . . . . ?
C4 N3 C3 C2 176.3(2) . . . . ?
