#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:07:18 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286158 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062556.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_7062556
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 Cl Cu N4 Se2'
_chemical_formula_sum            'C42 H40 Cl Cu N4 Se2'
_chemical_formula_weight         857.69
_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             2023-02-28
_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                 116.1600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1069(7)
_cell_length_b                   10.3068(3)
_cell_length_c                   14.1975(3)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.518
_cell_measurement_theta_min      2.444
_cell_volume                     3691.61(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      299.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22075
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.220
_diffrn_reflns_theta_min         2.134
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.8676.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       plate
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0332
_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)+(0.0283P)²+2.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             4099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01875j2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7062555--7062561.cif.'
_cod_original_cell_volume        3691.60(16)
_cod_database_code               7062556
_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   0.659
_shelx_estimated_absorpt_t_min   0.522
_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:
 C2(H2), C3(H3), C19(H19), C18(H18), C17(H17), C16(H16), C14(H14), C13(H13),
 C12(H12), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
_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
Se1 Se 0.43079(2) 0.85652(2) 0.75912(2) 0.04506(10) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.73325(5) 0.750000 0.05006(14) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 0.51566(10) 0.750000 0.0653(3) Uani 1 2 d S T P . .
C1 C 0.41528(9) 0.7290(2) 0.83484(19) 0.0360(6) Uani 1 1 d . . . . .
N1 N 0.38378(8) 0.62451(18) 0.79464(15) 0.0360(5) Uani 1 1 d . . . . .
N2 N 0.43435(8) 0.7209(2) 0.93988(16) 0.0414(5) Uani 1 1 d . . . . .
C2 C 0.38449(11) 0.5500(3) 0.8758(2) 0.0488(7) Uani 1 1 d . . . . .
H2 H 0.366311 0.472538 0.869334 0.059 Uiso 1 1 calc R U . . .
C3 C 0.41602(11) 0.6091(3) 0.9655(2) 0.0507(7) Uani 1 1 d . . . . .
H3 H 0.424103 0.580033 1.032861 0.061 Uiso 1 1 calc R U . . .
C4 C 0.47299(11) 0.8130(3) 1.0151(2) 0.0518(7) Uani 1 1 d . . . . .
H4 H 0.470712 0.894612 0.978000 0.062 Uiso 1 1 calc R U . . .
C6 C 0.52799(12) 0.7594(4) 1.0505(3) 0.0975(14) Uani 1 1 d . . . . .
H6A H 0.534143 0.742005 0.990322 0.146 Uiso 1 1 calc R U . . .
H6B H 0.531477 0.680413 1.088846 0.146 Uiso 1 1 calc R U . . .
H6C H 0.553460 0.821513 1.094833 0.146 Uiso 1 1 calc R U . . .
C5 C 0.45977(14) 0.8411(3) 1.1051(2) 0.0718(10) Uani 1 1 d . . . . .
H5A H 0.481096 0.912093 1.145725 0.108 Uiso 1 1 calc R U . . .
H5B H 0.466841 0.765608 1.148840 0.108 Uiso 1 1 calc R U . . .
H5C H 0.422958 0.863636 1.078173 0.108 Uiso 1 1 calc R U . . .
C7 C 0.35789(10) 0.5906(3) 0.68242(18) 0.0404(6) Uani 1 1 d . . . . .
H7A H 0.381444 0.536117 0.666191 0.049 Uiso 1 1 calc R U . . .
H7B H 0.351153 0.669091 0.640835 0.049 Uiso 1 1 calc R U . . .
C8 C 0.30622(9) 0.5198(2) 0.65353(17) 0.0364(6) Uani 1 1 d . . . . .
C21 C 0.25943(10) 0.5921(2) 0.62629(18) 0.0366(6) Uani 1 1 d . . . . .
C20 C 0.21019(10) 0.5263(3) 0.59690(19) 0.0417(6) Uani 1 1 d . . . . .
C19 C 0.16288(11) 0.6009(3) 0.5647(2) 0.0567(8) Uani 1 1 d . . . . .
H19 H 0.130601 0.558554 0.544109 0.068 Uiso 1 1 calc R U . . .
C18 C 0.16406(12) 0.7307(3) 0.5635(2) 0.0613(8) Uani 1 1 d . . . . .
H18 H 0.132661 0.777449 0.541239 0.074 Uiso 1 1 calc R U . . .
C17 C 0.21227(12) 0.7967(3) 0.5955(2) 0.0553(8) Uani 1 1 d . . . . .
H17 H 0.212621 0.886909 0.595657 0.066 Uiso 1 1 calc R U . . .
C16 C 0.25836(11) 0.7308(3) 0.6261(2) 0.0481(7) Uani 1 1 d . . . . .
H16 H 0.289934 0.776561 0.647394 0.058 Uiso 1 1 calc R U . . .
C14 C 0.20974(11) 0.3914(3) 0.5994(2) 0.0470(7) Uani 1 1 d . . . . .
H14 H 0.177731 0.348776 0.581339 0.056 Uiso 1 1 calc R U . . .
C15 C 0.25552(11) 0.3184(3) 0.62789(19) 0.0425(6) Uani 1 1 d . . . . .
C13 C 0.25444(13) 0.1805(3) 0.6310(2) 0.0547(8) Uani 1 1 d . . . . .
H13 H 0.222513 0.138000 0.614100 0.066 Uiso 1 1 calc R U . . .
C12 C 0.29905(14) 0.1108(3) 0.6580(2) 0.0632(9) Uani 1 1 d . . . . .
H12 H 0.297639 0.020661 0.659449 0.076 Uiso 1 1 calc R U . . .
C11 C 0.34773(13) 0.1730(3) 0.6841(2) 0.0586(8) Uani 1 1 d . . . . .
H11 H 0.378259 0.123603 0.703066 0.070 Uiso 1 1 calc R U . . .
C10 C 0.35081(11) 0.3041(3) 0.6821(2) 0.0482(7) Uani 1 1 d . . . . .
H10 H 0.383423 0.343182 0.699266 0.058 Uiso 1 1 calc R U . . .
C9 C 0.30491(10) 0.3833(2) 0.65408(18) 0.0372(6) 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'
Cl Cl 0.1484 0.1585 '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'
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 93.43(7) . . ?
Se1 Cu1 Se1 115.29(2) . 2_656 ?
Cl1 Cu1 Se1 122.354(12) . . ?
Cl1 Cu1 Se1 122.353(12) . 2_656 ?
N1 C1 Se1 126.44(18) . . ?
N2 C1 Se1 126.97(18) . . ?
N2 C1 N1 106.6(2) . . ?
C1 N1 C2 109.0(2) . . ?
C1 N1 C7 124.5(2) . . ?
C2 N1 C7 126.2(2) . . ?
C1 N2 C3 109.4(2) . . ?
C1 N2 C4 124.5(2) . . ?
C3 N2 C4 125.9(2) . . ?
N1 C2 H2 126.2 . . ?
C3 C2 N1 107.6(2) . . ?
C3 C2 H2 126.2 . . ?
N2 C3 H3 126.3 . . ?
C2 C3 N2 107.4(2) . . ?
C2 C3 H3 126.3 . . ?
N2 C4 H4 108.0 . . ?
N2 C4 C6 108.9(3) . . ?
N2 C4 C5 111.0(2) . . ?
C6 C4 H4 108.0 . . ?
C6 C4 C5 112.9(3) . . ?
C5 C4 H4 108.0 . . ?
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 . . ?
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 . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
N1 C7 C8 111.4(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C21 C8 C7 119.2(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 C21 120.5(2) . . ?
C8 C21 C20 119.7(2) . . ?
C8 C21 C16 123.1(2) . . ?
C20 C21 C16 117.2(2) . . ?
C19 C20 C21 119.0(2) . . ?
C14 C20 C21 119.1(2) . . ?
C14 C20 C19 122.0(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C19 C18 H18 119.8 . . ?
C19 C18 C17 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C21 C16 H16 119.4 . . ?
C17 C16 C21 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C20 C14 H14 118.9 . . ?
C15 C14 C20 122.1(2) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C13 121.4(3) . . ?
C14 C15 C9 119.3(2) . . ?
C13 C15 C9 119.3(3) . . ?
C15 C13 H13 119.6 . . ?
C12 C13 C15 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C11 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C8 C9 C15 119.3(2) . . ?
C8 C9 C10 123.4(2) . . ?
C10 C9 C15 117.2(2) . . ?
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
Se1 Cu1 2.3742(4) . ?
Se1 C1 1.867(2) . ?
Cu1 Cl1 2.2426(12) . ?
C1 N1 1.351(3) . ?
C1 N2 1.347(3) . ?
N1 C2 1.378(3) . ?
N1 C7 1.472(3) . ?
N2 C3 1.375(3) . ?
N2 C4 1.482(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.335(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9800 . ?
C4 C6 1.504(4) . ?
C4 C5 1.508(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(3) . ?
C8 C21 1.409(3) . ?
C8 C9 1.407(3) . ?
C21 C20 1.429(3) . ?
C21 C16 1.429(4) . ?
C20 C19 1.425(4) . ?
C20 C14 1.391(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.339(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.401(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.354(4) . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.388(4) . ?
C15 C13 1.423(4) . ?
C15 C9 1.435(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.346(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.405(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.355(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.427(4) . ?
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 N1 C2 176.85(19) . . . . ?
Se1 C1 N1 C7 2.8(3) . . . . ?
Se1 C1 N2 C3 -176.4(2) . . . . ?
Se1 C1 N2 C4 -1.6(4) . . . . ?
Cu1 Se1 C1 N1 -83.9(2) . . . . ?
Cu1 Se1 C1 N2 94.0(2) . . . . ?
C1 N1 C2 C3 0.4(3) . . . . ?
C1 N1 C7 C8 -150.1(2) . . . . ?
C1 N2 C3 C2 -1.6(3) . . . . ?
C1 N2 C4 C6 -94.2(3) . . . . ?
C1 N2 C4 C5 140.9(3) . . . . ?
N1 C1 N2 C3 1.8(3) . . . . ?
N1 C1 N2 C4 176.7(2) . . . . ?
N1 C2 C3 N2 0.7(3) . . . . ?
N1 C7 C8 C21 86.4(3) . . . . ?
N1 C7 C8 C9 -93.5(3) . . . . ?
N2 C1 N1 C2 -1.4(3) . . . . ?
N2 C1 N1 C7 -175.4(2) . . . . ?
C2 N1 C7 C8 37.0(3) . . . . ?
C3 N2 C4 C6 79.7(4) . . . . ?
C3 N2 C4 C5 -45.1(4) . . . . ?
C4 N2 C3 C2 -176.3(3) . . . . ?
C7 N1 C2 C3 174.3(2) . . . . ?
C7 C8 C21 C20 178.8(2) . . . . ?
C7 C8 C21 C16 -1.0(4) . . . . ?
C7 C8 C9 C15 179.1(2) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C8 C21 C20 C19 -177.0(2) . . . . ?
C8 C21 C20 C14 2.3(4) . . . . ?
C8 C21 C16 C17 177.4(3) . . . . ?
C21 C8 C9 C15 -0.8(3) . . . . ?
C21 C8 C9 C10 -179.2(2) . . . . ?
C21 C20 C19 C18 -1.3(4) . . . . ?
C21 C20 C14 C15 -1.1(4) . . . . ?
C20 C21 C16 C17 -2.4(4) . . . . ?
C20 C19 C18 C17 -0.9(5) . . . . ?
C20 C14 C15 C13 179.4(3) . . . . ?
C20 C14 C15 C9 -1.1(4) . . . . ?
C19 C20 C14 C15 178.2(3) . . . . ?
C19 C18 C17 C16 1.4(5) . . . . ?
C18 C17 C16 C21 0.4(4) . . . . ?
C16 C21 C20 C19 2.9(4) . . . . ?
C16 C21 C20 C14 -177.9(2) . . . . ?
C14 C20 C19 C18 179.5(3) . . . . ?
C14 C15 C13 C12 179.5(3) . . . . ?
C14 C15 C9 C8 2.0(4) . . . . ?
C14 C15 C9 C10 -179.5(2) . . . . ?
C15 C13 C12 C11 0.2(5) . . . . ?
C13 C15 C9 C8 -178.5(2) . . . . ?
C13 C15 C9 C10 0.0(4) . . . . ?
C13 C12 C11 C10 -0.4(5) . . . . ?
C12 C11 C10 C9 0.4(5) . . . . ?
C11 C10 C9 C8 178.2(3) . . . . ?
C11 C10 C9 C15 -0.2(4) . . . . ?
C9 C8 C21 C20 -1.3(3) . . . . ?
C9 C8 C21 C16 178.9(2) . . . . ?
C9 C15 C13 C12 0.0(4) . . . . ?
