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#$Date: 2024-10-06 12:18:39 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295342 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160126.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_7160126
loop_
_publ_author_name
'Ghosh, Kingkar'
'Ghosh, Narendra Nath'
'Choudhury, Prasun'
'Bhattacharjee, Subham'
'Saha, Rajat'
'Deb, Mayukh'
'Biswas, Kinkar'
_publ_section_title
;
 A benzimidazole-based Cu(ii) complex catalyzed site-selective C--H
 sulfenylation of imidazo-[1,2-a]pyridines using CS2 as a sulfur source
;
_journal_issue                   38
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              7791
_journal_page_last               7800
_journal_paper_doi               10.1039/D4OB00868E
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H17 Cl N2 S'
_chemical_formula_sum            'C21 H17 Cl N2 S'
_chemical_formula_weight         364.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-04-15 deposited with the CCDC.	2024-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                101.374(7)
_cell_angle_beta                 107.360(6)
_cell_angle_gamma                90.842(8)
_cell_formula_units_Z            2
_cell_length_a                   7.7958(9)
_cell_length_b                   11.0760(19)
_cell_length_c                   11.1247(14)
_cell_measurement_reflns_used    2596
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.813
_cell_measurement_theta_min      4.830
_cell_volume                     896.0(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7361
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.746
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.746
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.746
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1755P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2641
_reflns_number_total             4183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00868e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7160125--7160126.cif.'
_cod_database_code               7160126
_shelx_shelxl_version_number     2014/7
_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_min   0.906
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.39919(12) 0.05102(8) 0.71740(10) 0.0921(3) Uani 1 1 d . . . . .
S1 S 0.59112(8) 0.71751(6) 0.83558(6) 0.0591(2) Uani 1 1 d . . . . .
N1 N 0.7776(2) 0.52309(19) 0.56826(19) 0.0513(5) Uani 1 1 d . . . . .
N2 N 0.7660(2) 0.71969(18) 0.65743(19) 0.0505(5) Uani 1 1 d . . . . .
C1 C -0.0267(5) 0.7911(6) 1.1305(3) 0.139(2) Uani 1 1 d . . . . .
H1A H 0.0609 0.8147 1.2142 0.208 Uiso 1 1 calc R U . . .
H1B H -0.0937 0.7157 1.1250 0.208 Uiso 1 1 calc R U . . .
H1C H -0.1076 0.8551 1.1169 0.208 Uiso 1 1 calc R U . . .
C2 C 0.0679(4) 0.7719(4) 1.0289(3) 0.0841(11) Uani 1 1 d . . . . .
C3 C 0.0638(4) 0.6591(4) 0.9519(3) 0.0864(10) Uani 1 1 d . . . . .
H3 H -0.0030 0.5929 0.9606 0.104 Uiso 1 1 calc R U . . .
C4 C 0.1549(4) 0.6389(3) 0.8612(3) 0.0684(7) Uani 1 1 d . . . . .
H4 H 0.1511 0.5602 0.8116 0.082 Uiso 1 1 calc R U . . .
C5 C 0.2506(3) 0.7355(2) 0.8449(2) 0.0542(6) Uani 1 1 d . . . . .
C8 C 0.3512(3) 0.7164(3) 0.7486(2) 0.0593(6) Uani 1 1 d . . . . .
H8A H 0.3315 0.7818 0.7005 0.071 Uiso 1 1 calc R U . . .
H8B H 0.3094 0.6380 0.6883 0.071 Uiso 1 1 calc R U . . .
C9 C 0.6776(3) 0.6494(2) 0.7144(2) 0.0493(5) Uani 1 1 d . . . . .
C10 C 0.6886(3) 0.5284(2) 0.6571(2) 0.0467(5) Uani 1 1 d . . . . .
C11 C 0.6196(3) 0.4133(2) 0.6776(2) 0.0468(5) Uani 1 1 d . . . . .
C16 C 0.6249(3) 0.3036(2) 0.5944(2) 0.0549(6) Uani 1 1 d . . . . .
H16 H 0.6746 0.3055 0.5284 0.066 Uiso 1 1 calc R U . . .
C15 C 0.5597(3) 0.1925(2) 0.6058(3) 0.0613(6) Uani 1 1 d . . . . .
H15 H 0.5638 0.1201 0.5482 0.074 Uiso 1 1 calc R U . . .
C14 C 0.4878(3) 0.1904(3) 0.7044(3) 0.0612(6) Uani 1 1 d . . . . .
C12 C 0.5492(4) 0.4068(3) 0.7772(3) 0.0636(7) Uani 1 1 d . . . . .
H12 H 0.5466 0.4786 0.8361 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4831(4) 0.2957(3) 0.7903(3) 0.0697(7) Uani 1 1 d . . . . .
H13 H 0.4356 0.2926 0.8571 0.084 Uiso 1 1 calc R U . . .
C17 C 0.8244(3) 0.6378(2) 0.5697(2) 0.0510(5) Uani 1 1 d . . . . .
C7 C 0.1622(5) 0.8677(4) 1.0098(3) 0.0855(10) Uani 1 1 d . . . . .
H7 H 0.1652 0.9466 1.0587 0.103 Uiso 1 1 calc R U . . .
C6 C 0.2525(4) 0.8495(3) 0.9196(3) 0.0706(7) Uani 1 1 d . . . . .
H6 H 0.3163 0.9163 0.9093 0.085 Uiso 1 1 calc R U . . .
C21 C 0.8000(3) 0.8449(3) 0.6776(3) 0.0647(7) Uani 1 1 d . . . . .
H21 H 0.7591 0.8985 0.7368 0.078 Uiso 1 1 calc R U . . .
C20 C 0.8941(4) 0.8884(3) 0.6096(3) 0.0759(8) Uani 1 1 d . . . . .
H20 H 0.9183 0.9732 0.6223 0.091 Uiso 1 1 calc R U . . .
C19 C 0.9562(4) 0.8094(3) 0.5208(3) 0.0740(8) Uani 1 1 d . . . . .
H19 H 1.0216 0.8418 0.4753 0.089 Uiso 1 1 calc R U . . .
C18 C 0.9219(3) 0.6858(3) 0.5001(3) 0.0630(7) Uani 1 1 d . . . . .
H18 H 0.9626 0.6330 0.4401 0.076 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'
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'
Cl Cl 0.1484 0.1585 '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
C9 S1 C8 102.25(10) . . ?
C17 N1 C10 106.34(19) . . ?
C21 N2 C9 131.0(2) . . ?
C21 N2 C17 122.2(2) . . ?
C9 N2 C17 106.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.8(3) . . ?
C7 C2 C1 121.2(4) . . ?
C3 C2 C1 122.0(4) . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 C8 121.0(3) . . ?
C4 C5 C8 120.7(2) . . ?
C5 C8 S1 108.09(16) . . ?
C5 C8 H8A 110.1 . . ?
S1 C8 H8A 110.1 . . ?
C5 C8 H8B 110.1 . . ?
S1 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C10 104.86(19) . . ?
N2 C9 S1 121.35(18) . . ?
C10 C9 S1 133.72(19) . . ?
N1 C10 C9 110.9(2) . . ?
N1 C10 C11 119.0(2) . . ?
C9 C10 C11 130.1(2) . . ?
C16 C11 C12 117.4(2) . . ?
C16 C11 C10 118.9(2) . . ?
C12 C11 C10 123.7(2) . . ?
C11 C16 C15 122.3(2) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 Cl1 119.0(2) . . ?
C13 C14 Cl1 119.7(2) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N1 C17 C18 130.6(2) . . ?
N1 C17 N2 111.2(2) . . ?
C18 C17 N2 118.3(2) . . ?
C2 C7 C6 121.2(3) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C20 C21 N2 118.3(3) . . ?
C20 C21 H21 120.9 . . ?
N2 C21 H21 120.9 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
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
Cl1 C14 1.731(3) . ?
S1 C9 1.732(2) . ?
S1 C8 1.830(2) . ?
N1 C17 1.312(3) . ?
N1 C10 1.360(3) . ?
N2 C21 1.370(3) . ?
N2 C9 1.386(3) . ?
N2 C17 1.382(3) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.368(6) . ?
C2 C3 1.363(5) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(4) . ?
C5 C8 1.492(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.382(3) . ?
C10 C11 1.461(3) . ?
C11 C16 1.384(3) . ?
C11 C12 1.388(3) . ?
C16 C15 1.368(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.376(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.363(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C17 C18 1.401(3) . ?
C7 C6 1.374(4) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C21 C20 1.343(4) . ?
C21 H21 0.9300 . ?
C20 C19 1.391(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.352(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
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
C7 C2 C3 C4 2.3(5) . . . . ?
C1 C2 C3 C4 -177.8(3) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C8 179.5(2) . . . . ?
C6 C5 C8 S1 75.7(3) . . . . ?
C4 C5 C8 S1 -103.8(2) . . . . ?
C9 S1 C8 C5 162.61(19) . . . . ?
C21 N2 C9 C10 -178.7(2) . . . . ?
C17 N2 C9 C10 0.1(2) . . . . ?
C21 N2 C9 S1 -1.5(3) . . . . ?
C17 N2 C9 S1 177.40(15) . . . . ?
C8 S1 C9 N2 100.67(19) . . . . ?
C8 S1 C9 C10 -83.0(2) . . . . ?
C17 N1 C10 C9 0.7(2) . . . . ?
C17 N1 C10 C11 -179.86(19) . . . . ?
N2 C9 C10 N1 -0.5(2) . . . . ?
S1 C9 C10 N1 -177.31(17) . . . . ?
N2 C9 C10 C11 -179.8(2) . . . . ?
S1 C9 C10 C11 3.4(4) . . . . ?
N1 C10 C11 C16 -8.7(3) . . . . ?
C9 C10 C11 C16 170.5(2) . . . . ?
N1 C10 C11 C12 170.8(2) . . . . ?
C9 C10 C11 C12 -9.9(4) . . . . ?
C12 C11 C16 C15 1.7(4) . . . . ?
C10 C11 C16 C15 -178.7(2) . . . . ?
C11 C16 C15 C14 -0.6(4) . . . . ?
C16 C15 C14 C13 -0.8(4) . . . . ?
C16 C15 C14 Cl1 178.3(2) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
C10 C11 C12 C13 178.8(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C15 C14 C13 C12 0.9(4) . . . . ?
Cl1 C14 C13 C12 -178.2(2) . . . . ?
C10 N1 C17 C18 178.4(2) . . . . ?
C10 N1 C17 N2 -0.7(2) . . . . ?
C21 N2 C17 N1 179.3(2) . . . . ?
C9 N2 C17 N1 0.3(2) . . . . ?
C21 N2 C17 C18 0.2(3) . . . . ?
C9 N2 C17 C18 -178.8(2) . . . . ?
C3 C2 C7 C6 -1.9(5) . . . . ?
C1 C2 C7 C6 178.2(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C8 C5 C6 C7 -179.1(3) . . . . ?
C2 C7 C6 C5 0.5(5) . . . . ?
C9 N2 C21 C20 178.4(2) . . . . ?
C17 N2 C21 C20 -0.3(4) . . . . ?
N2 C21 C20 C19 0.0(4) . . . . ?
C21 C20 C19 C18 0.4(5) . . . . ?
C20 C19 C18 C17 -0.5(4) . . . . ?
N1 C17 C18 C19 -178.7(3) . . . . ?
N2 C17 C18 C19 0.2(4) . . . . ?
