#------------------------------------------------------------------------------
#$Date: 2025-05-14 13:17:04 +0300 (Wed, 14 May 2025) $
#$Revision: 299663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568539.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_1568539
loop_
_publ_author_name
'Nan, Jiang'
'Ren, Xin'
'Yan, Qiang'
'Liu, Shilei'
'Wang, Jing'
'Ma, Yangmin'
'Szostak, Michal'
_publ_section_title
;
 Hypervalent iodine-promoted twofold oxidative coupling of amines with
 amides and thioamides: chemoselective pathway to oxazoles and thiazoles.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3338
_journal_page_last               3345
_journal_paper_doi               10.1039/d3sc00301a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dnkbz
_audit_creation_date             2022-12-03
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2022-12-05 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.817(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5785(6)
_cell_length_b                   19.2356(16)
_cell_length_c                   13.4588(11)
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.596
_cell_measurement_theta_min      2.604
_cell_volume                     1959.6(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0827
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49798
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.604
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8784.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0731
_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)+(0.0273P)²+3.8582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2321
_reflns_number_total             3431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00301a2.cif
_cod_data_source_block           sust_3454_0m
_cod_depositor_comments
;
Adding full bibliography for 1568538--1568539.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H18 N2 S2'
_cod_original_formula_weight         398.52
_cod_original_formula_moiety         '2(C12 H9 N S)'
_cod_original_formula_units_Z            4
_cod_database_code               1568539
_shelx_shelxl_version_number     2019/2
_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   0.961
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C16(H16), C17(H17), C18(H18), C21(H21), C9(H9), C12(H12),
 C13(H13), C15(H15), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
S1 S 0.30787(17) 0.67991(7) 0.62845(10) 0.0583(4) Uani 1 1 d . . . . .
N2 N -0.0213(5) 0.6468(2) 0.6029(3) 0.0593(11) Uani 1 1 d . . . . .
C2 C 0.3717(7) 0.9204(3) 0.6356(4) 0.0601(13) Uani 1 1 d . . . . .
H2 H 0.484076 0.939658 0.643701 0.072 Uiso 1 1 calc R U . . .
C3 C -0.0130(5) 0.7189(2) 0.6056(3) 0.0468(11) Uani 1 1 d . . . . .
C5 C 0.0613(6) 0.9354(2) 0.6135(3) 0.0530(12) Uani 1 1 d . . . . .
H5 H -0.037012 0.964304 0.606662 0.064 Uiso 1 1 calc R U . . .
C6 C 0.1860(5) 0.8193(2) 0.6215(3) 0.0427(10) Uani 1 1 d . . . . .
C14 C 0.0361(5) 0.8622(2) 0.6106(3) 0.0481(11) Uani 1 1 d . . . . .
C16 C -0.1607(6) 0.7626(3) 0.5947(4) 0.0561(13) Uani 1 1 d . . . . .
H16 H -0.273726 0.744084 0.585528 0.067 Uiso 1 1 calc R U . . .
C17 C 0.3533(6) 0.8497(3) 0.6332(3) 0.0557(12) Uani 1 1 d . . . . .
H17 H 0.453026 0.821578 0.639446 0.067 Uiso 1 1 calc R U . . .
C18 C -0.1357(6) 0.8322(3) 0.5979(3) 0.0549(12) Uani 1 1 d . . . . .
H18 H -0.233417 0.861394 0.591662 0.066 Uiso 1 1 calc R U . . .
C19 C 0.2235(7) 0.9646(3) 0.6261(4) 0.0602(13) Uani 1 1 d . . . . .
C21 C 0.1368(7) 0.6218(3) 0.6138(4) 0.0606(13) Uani 1 1 d . . . . .
H21 H 0.157025 0.574157 0.613833 0.073 Uiso 1 1 calc R U . . .
C23 C 0.2483(8) 1.0427(3) 0.6293(5) 0.0867(19) Uani 1 1 d . . . . .
H23A H 0.279726 1.056920 0.696238 0.130 Uiso 1 1 calc R U . . .
H23B H 0.140275 1.065139 0.607065 0.130 Uiso 1 1 calc R U . . .
H23C H 0.340732 1.055693 0.586629 0.130 Uiso 1 1 calc R U . . .
C24 C 0.1554(5) 0.7460(2) 0.6184(3) 0.0439(11) Uani 1 1 d . . . . .
S2 S 0.80635(17) 0.48226(7) 0.62770(11) 0.0621(4) Uani 1 1 d . . . . .
N1 N 0.4770(5) 0.5162(2) 0.6215(3) 0.0561(10) Uani 1 1 d . . . . .
C1 C 0.6827(5) 0.3434(2) 0.6355(3) 0.0405(10) Uani 1 1 d . . . . .
C4 C 0.5320(5) 0.3002(2) 0.6331(3) 0.0418(10) Uani 1 1 d . . . . .
C7 C 0.7214(6) 0.1982(2) 0.6404(3) 0.0519(12) Uani 1 1 d . . . . .
C8 C 0.6530(6) 0.4170(2) 0.6314(3) 0.0447(11) Uani 1 1 d . . . . .
C9 C 0.6337(7) 0.5410(3) 0.6207(4) 0.0611(13) Uani 1 1 d . . . . .
H9 H 0.653794 0.588546 0.616649 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4856(6) 0.4440(2) 0.6266(3) 0.0494(11) Uani 1 1 d . . . . .
C11 C 0.7440(7) 0.1201(3) 0.6414(4) 0.0689(15) Uani 1 1 d . . . . .
H11A H 0.655335 0.099480 0.680620 0.103 Uiso 1 1 calc R U . . .
H11B H 0.859024 0.108542 0.669627 0.103 Uiso 1 1 calc R U . . .
H11C H 0.731799 0.102653 0.574581 0.103 Uiso 1 1 calc R U . . .
C12 C 0.3628(6) 0.3301(3) 0.6270(4) 0.0560(12) Uani 1 1 d . . . . .
H12 H 0.264343 0.301173 0.625278 0.067 Uiso 1 1 calc R U . . .
C13 C 0.8681(6) 0.2423(3) 0.6428(3) 0.0541(12) Uani 1 1 d . . . . .
H13 H 0.980611 0.222874 0.646147 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3384(6) 0.4001(3) 0.6234(4) 0.0585(13) Uani 1 1 d . . . . .
H15 H 0.224915 0.418586 0.618994 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8517(6) 0.3129(3) 0.6405(3) 0.0518(12) Uani 1 1 d . . . . .
H20 H 0.952012 0.340765 0.642304 0.062 Uiso 1 1 calc R U . . .
C22 C 0.5555(6) 0.2274(2) 0.6363(3) 0.0492(11) Uani 1 1 d . . . . .
H22 H 0.456872 0.198632 0.635579 0.059 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'
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
C21 S1 C24 88.3(2) . . ?
C21 N2 C3 109.1(4) . . ?
C17 C2 H2 119.4 . . ?
C17 C2 C19 121.2(5) . . ?
C19 C2 H2 119.4 . . ?
N2 C3 C16 124.1(4) . . ?
C24 C3 N2 114.9(4) . . ?
C24 C3 C16 120.9(4) . . ?
C14 C5 H5 118.9 . . ?
C19 C5 H5 118.9 . . ?
C19 C5 C14 122.2(5) . . ?
C14 C6 C24 116.5(4) . . ?
C17 C6 C14 119.4(4) . . ?
C17 C6 C24 124.1(4) . . ?
C5 C14 C18 121.7(4) . . ?
C6 C14 C5 118.1(4) . . ?
C6 C14 C18 120.2(4) . . ?
C3 C16 H16 120.6 . . ?
C18 C16 C3 118.7(4) . . ?
C18 C16 H16 120.6 . . ?
C2 C17 C6 120.6(4) . . ?
C2 C17 H17 119.7 . . ?
C6 C17 H17 119.7 . . ?
C14 C18 H18 119.0 . . ?
C16 C18 C14 122.0(4) . . ?
C16 C18 H18 119.0 . . ?
C2 C19 C23 119.9(5) . . ?
C5 C19 C2 118.4(5) . . ?
C5 C19 C23 121.7(5) . . ?
S1 C21 H21 121.2 . . ?
N2 C21 S1 117.6(4) . . ?
N2 C21 H21 121.2 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 S1 110.1(4) . . ?
C3 C24 C6 121.6(4) . . ?
C6 C24 S1 128.3(3) . . ?
C8 S2 C9 88.1(2) . . ?
C9 N1 C10 109.2(4) . . ?
C4 C1 C8 117.1(4) . . ?
C20 C1 C4 119.2(4) . . ?
C20 C1 C8 123.7(4) . . ?
C12 C4 C1 119.7(4) . . ?
C12 C4 C22 121.5(4) . . ?
C22 C4 C1 118.9(4) . . ?
C13 C7 C11 120.9(4) . . ?
C22 C7 C11 120.6(5) . . ?
C22 C7 C13 118.5(4) . . ?
C1 C8 S2 128.2(3) . . ?
C10 C8 S2 110.3(3) . . ?
C10 C8 C1 121.4(4) . . ?
S2 C9 H9 121.4 . . ?
N1 C9 S2 117.2(4) . . ?
N1 C9 H9 121.4 . . ?
N1 C10 C15 124.5(4) . . ?
C8 C10 N1 115.0(4) . . ?
C8 C10 C15 120.5(4) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12 119.0 . . ?
C15 C12 C4 122.0(5) . . ?
C15 C12 H12 119.0 . . ?
C7 C13 H13 118.9 . . ?
C20 C13 C7 122.2(4) . . ?
C20 C13 H13 118.9 . . ?
C10 C15 H15 120.3 . . ?
C12 C15 C10 119.4(5) . . ?
C12 C15 H15 120.3 . . ?
C1 C20 H20 120.0 . . ?
C13 C20 C1 119.9(4) . . ?
C13 C20 H20 120.0 . . ?
C4 C22 H22 119.3 . . ?
C7 C22 C4 121.3(4) . . ?
C7 C22 H22 119.3 . . ?
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
S1 C21 1.715(5) . ?
S1 C24 1.719(4) . ?
N2 C3 1.388(6) . ?
N2 C21 1.292(6) . ?
C2 H2 0.9300 . ?
C2 C17 1.367(6) . ?
C2 C19 1.410(7) . ?
C3 C16 1.402(6) . ?
C3 C24 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C14 1.421(6) . ?
C5 C19 1.354(6) . ?
C6 C14 1.406(6) . ?
C6 C17 1.398(6) . ?
C6 C24 1.430(6) . ?
C14 C18 1.426(6) . ?
C16 H16 0.9300 . ?
C16 C18 1.353(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C23 1.516(7) . ?
C21 H21 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
S2 C8 1.714(4) . ?
S2 C9 1.727(5) . ?
N1 C9 1.280(6) . ?
N1 C10 1.392(6) . ?
C1 C4 1.412(6) . ?
C1 C8 1.433(6) . ?
C1 C20 1.408(6) . ?
C4 C12 1.405(6) . ?
C4 C22 1.411(6) . ?
C7 C11 1.513(7) . ?
C7 C13 1.397(6) . ?
C7 C22 1.376(6) . ?
C8 C10 1.370(6) . ?
C9 H9 0.9300 . ?
C10 C15 1.399(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C15 1.359(7) . ?
C13 H13 0.9300 . ?
C13 C20 1.363(6) . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22 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
N2 C3 C16 C18 -179.4(4) . . . . ?
N2 C3 C24 S1 -0.6(5) . . . . ?
N2 C3 C24 C6 179.2(4) . . . . ?
C3 N2 C21 S1 0.1(6) . . . . ?
C3 C16 C18 C14 0.9(7) . . . . ?
C5 C14 C18 C16 179.8(5) . . . . ?
C6 C14 C18 C16 -0.8(7) . . . . ?
C14 C5 C19 C2 0.5(7) . . . . ?
C14 C5 C19 C23 -179.9(5) . . . . ?
C14 C6 C17 C2 1.0(7) . . . . ?
C14 C6 C24 S1 179.5(3) . . . . ?
C14 C6 C24 C3 -0.1(6) . . . . ?
C16 C3 C24 S1 -179.5(4) . . . . ?
C16 C3 C24 C6 0.2(7) . . . . ?
C17 C2 C19 C5 -0.5(7) . . . . ?
C17 C2 C19 C23 179.8(5) . . . . ?
C17 C6 C14 C5 -1.0(6) . . . . ?
C17 C6 C14 C18 179.6(4) . . . . ?
C17 C6 C24 S1 0.3(7) . . . . ?
C17 C6 C24 C3 -179.3(4) . . . . ?
C19 C2 C17 C6 -0.2(7) . . . . ?
C19 C5 C14 C6 0.2(7) . . . . ?
C19 C5 C14 C18 179.6(5) . . . . ?
C21 S1 C24 C3 0.5(3) . . . . ?
C21 S1 C24 C6 -179.2(4) . . . . ?
C21 N2 C3 C16 179.2(4) . . . . ?
C21 N2 C3 C24 0.3(6) . . . . ?
C24 S1 C21 N2 -0.3(4) . . . . ?
C24 C3 C16 C18 -0.6(7) . . . . ?
C24 C6 C14 C5 179.8(4) . . . . ?
C24 C6 C14 C18 0.4(6) . . . . ?
C24 C6 C17 C2 -179.9(4) . . . . ?
S2 C8 C10 N1 -1.0(5) . . . . ?
S2 C8 C10 C15 176.8(4) . . . . ?
N1 C10 C15 C12 178.7(4) . . . . ?
C1 C4 C12 C15 -0.2(7) . . . . ?
C1 C4 C22 C7 -0.8(6) . . . . ?
C1 C8 C10 N1 -179.0(4) . . . . ?
C1 C8 C10 C15 -1.2(7) . . . . ?
C4 C1 C8 S2 -177.0(3) . . . . ?
C4 C1 C8 C10 0.7(6) . . . . ?
C4 C1 C20 C13 0.1(6) . . . . ?
C4 C12 C15 C10 -0.4(7) . . . . ?
C7 C13 C20 C1 0.0(7) . . . . ?
C8 S2 C9 N1 0.3(4) . . . . ?
C8 C1 C4 C12 0.0(6) . . . . ?
C8 C1 C4 C22 179.6(4) . . . . ?
C8 C1 C20 C13 -179.1(4) . . . . ?
C8 C10 C15 C12 1.1(7) . . . . ?
C9 S2 C8 C1 178.3(4) . . . . ?
C9 S2 C8 C10 0.4(3) . . . . ?
C9 N1 C10 C8 1.2(6) . . . . ?
C9 N1 C10 C15 -176.5(5) . . . . ?
C10 N1 C9 S2 -0.9(5) . . . . ?
C11 C7 C13 C20 179.0(5) . . . . ?
C11 C7 C22 C4 -178.6(4) . . . . ?
C12 C4 C22 C7 178.8(4) . . . . ?
C13 C7 C22 C4 0.9(7) . . . . ?
C20 C1 C4 C12 -179.3(4) . . . . ?
C20 C1 C4 C22 0.3(6) . . . . ?
C20 C1 C8 S2 2.3(6) . . . . ?
C20 C1 C8 C10 180.0(4) . . . . ?
C22 C4 C12 C15 -179.7(5) . . . . ?
C22 C7 C13 C20 -0.5(7) . . . . ?
