#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:49:03 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268614 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128584.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_7128584
loop_
_publ_author_name
'Wang, Yuna'
'Qi, Zaojuan'
'Niu, Yanning'
'Feng, Hua'
'Benassi, Enrico'
'Qian, Bo'
_publ_section_title
;
 Selective oxidative intermolecular carbosulphenylation of aryl alkenes
 with thiols and nucleophiles via a 1,2-dithioethane intermediate.
;
_journal_issue                   61
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7533
_journal_page_last               7536
_journal_paper_doi               10.1039/d1cc02517a
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C26 H24 O S'
_chemical_formula_weight         384.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2021-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6661(19)
_cell_length_b                   13.863(3)
_cell_length_c                   19.578(5)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.85
_cell_measurement_theta_min      2.55
_cell_volume                     2080.7(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17187
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.965
_diffrn_reflns_theta_min         1.800
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7458
_exptl_transmission_factor_min   0.5886
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1143 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0442
_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)+(0.0500P)²+0.1776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                3398
_reflns_number_total             5153
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02517a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7128584.cif.
;
_cod_database_code               7128584
_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   0.951
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.3513(4) 0.65230(19) 0.54599(14) 0.0515(7) Uani 1 1 d . . . . .
H1 H 0.3550 0.6575 0.5933 0.062 Uiso 1 1 calc R U . . .
C2 C 0.4118(4) 0.7279(2) 0.50649(17) 0.0646(8) Uani 1 1 d . . . . .
H2 H 0.4570 0.7828 0.5272 0.078 Uiso 1 1 calc R U . . .
C3 C 0.4048(5) 0.7218(2) 0.43641(17) 0.0664(9) Uani 1 1 d . . . . .
H3 H 0.4458 0.7723 0.4097 0.080 Uiso 1 1 calc R U . . .
C4 C 0.3375(5) 0.6412(2) 0.40623(15) 0.0665(9) Uani 1 1 d . . . . .
H4 H 0.3313 0.6375 0.3589 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2782(4) 0.5649(2) 0.44572(13) 0.0556(8) Uani 1 1 d . . . . .
H5 H 0.2330 0.5103 0.4245 0.067 Uiso 1 1 calc R U . . .
C6 C 0.2857(4) 0.56912(17) 0.51675(12) 0.0436(6) Uani 1 1 d . . . . .
C7 C 0.2289(4) 0.48602(17) 0.56275(11) 0.0429(6) Uani 1 1 d . . . . .
H7 H 0.3171 0.4821 0.5989 0.051 Uiso 1 1 calc R U . . .
C8 C 0.0580(4) 0.50915(17) 0.59881(12) 0.0428(6) Uani 1 1 d . . . . .
C9 C 0.0535(4) 0.53224(17) 0.66993(13) 0.0465(7) Uani 1 1 d . . . . .
C10 C 0.2021(5) 0.53298(19) 0.71261(13) 0.0543(7) Uani 1 1 d . . . . .
H10 H 0.3094 0.5156 0.6942 0.065 Uiso 1 1 calc R U . . .
C11 C 0.1934(6) 0.5584(2) 0.77999(14) 0.0684(9) Uani 1 1 d . . . . .
H11 H 0.2946 0.5591 0.8062 0.082 Uiso 1 1 calc R U . . .
C12 C 0.0356(7) 0.5831(2) 0.80964(17) 0.0825(13) Uani 1 1 d . . . . .
H12 H 0.0307 0.5997 0.8556 0.099 Uiso 1 1 calc R U . . .
C13 C -0.1106(6) 0.5828(2) 0.77164(19) 0.0777(12) Uani 1 1 d . . . . .
H13 H -0.2162 0.5992 0.7919 0.093 Uiso 1 1 calc R U . . .
C14 C -0.1075(5) 0.55824(19) 0.70161(16) 0.0587(8) Uani 1 1 d . . . . .
C15 C -0.2572(5) 0.5604(2) 0.6617(2) 0.0737(10) Uani 1 1 d . . . . .
H15 H -0.3626 0.5776 0.6819 0.088 Uiso 1 1 calc R U . . .
C16 C -0.2543(4) 0.5379(2) 0.5936(2) 0.0713(9) Uani 1 1 d . . . . .
H16 H -0.3568 0.5388 0.5682 0.086 Uiso 1 1 calc R U . . .
C17 C -0.0960(4) 0.5138(2) 0.56277(15) 0.0553(7) Uani 1 1 d . . . . .
C18 C -0.2344(6) 0.5021(4) 0.4530(2) 0.0995(13) Uani 1 1 d . . . . .
H18A H -0.3184 0.4550 0.4676 0.149 Uiso 1 1 calc R U . . .
H18B H -0.2041 0.4906 0.4062 0.149 Uiso 1 1 calc R U . . .
H18C H -0.2833 0.5655 0.4575 0.149 Uiso 1 1 calc R U . . .
C19 C 0.2314(5) 0.38715(18) 0.52697(13) 0.0569(8) Uani 1 1 d . . . . .
H19A H 0.3428 0.3792 0.5041 0.068 Uiso 1 1 calc R U . . .
H19B H 0.1411 0.3861 0.4923 0.068 Uiso 1 1 calc R U . . .
C20 C 0.3818(4) 0.29397(18) 0.63903(15) 0.0525(7) Uani 1 1 d . . . . .
C21 C 0.5517(5) 0.2936(2) 0.61403(16) 0.0685(9) Uani 1 1 d . . . . .
H21 H 0.5715 0.2893 0.5673 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6926(5) 0.2996(2) 0.65903(18) 0.0710(9) Uani 1 1 d . . . . .
H22 H 0.8054 0.3005 0.6416 0.085 Uiso 1 1 calc R U . . .
C23 C 0.6683(5) 0.30427(19) 0.72823(17) 0.0609(8) Uani 1 1 d . . . . .
C24 C 0.5002(6) 0.3028(2) 0.75198(18) 0.0691(9) Uani 1 1 d . . . . .
H24 H 0.4807 0.3049 0.7988 0.083 Uiso 1 1 calc R U . . .
C25 C 0.3590(5) 0.2981(2) 0.70843(17) 0.0660(9) Uani 1 1 d . . . . .
H25 H 0.2467 0.2978 0.7264 0.079 Uiso 1 1 calc R U . . .
C26 C 0.8214(6) 0.3114(3) 0.7760(2) 0.0882(12) Uani 1 1 d . . . . .
H26A H 0.8932 0.3651 0.7629 0.132 Uiso 1 1 calc R U . . .
H26B H 0.8885 0.2530 0.7737 0.132 Uiso 1 1 calc R U . . .
H26C H 0.7802 0.3207 0.8218 0.132 Uiso 1 1 calc R U . . .
O1 O -0.0838(3) 0.49489(17) 0.49389(10) 0.0709(6) Uani 1 1 d . . . . .
S1 S 0.19811(13) 0.28629(5) 0.58443(4) 0.0690(3) 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'
O O 0.0106 0.0060 '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
C6 C1 C2 121.5(3) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 119.3(2) . . ?
C5 C6 C7 123.1(2) . . ?
C8 C7 C6 111.1(2) . . ?
C8 C7 C19 114.2(2) . . ?
C6 C7 C19 113.6(2) . . ?
C8 C7 H7 105.7 . . ?
C6 C7 H7 105.7 . . ?
C19 C7 H7 105.7 . . ?
C17 C8 C9 117.9(3) . . ?
C17 C8 C7 120.7(2) . . ?
C9 C8 C7 121.3(2) . . ?
C10 C9 C14 116.0(2) . . ?
C10 C9 C8 123.9(3) . . ?
C14 C9 C8 120.1(3) . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 C9 118.4(3) . . ?
C13 C14 C9 119.8(4) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C8 C17 O1 115.8(3) . . ?
C8 C17 C16 122.3(3) . . ?
O1 C17 C16 121.9(3) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 S1 113.74(18) . . ?
C7 C19 H19A 108.8 . . ?
S1 C19 H19A 108.8 . . ?
C7 C19 H19B 108.8 . . ?
S1 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C25 C20 C21 117.9(3) . . ?
C25 C20 S1 119.9(3) . . ?
C21 C20 S1 122.1(2) . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 117.6(3) . . ?
C22 C23 C26 120.8(4) . . ?
C24 C23 C26 121.6(3) . . ?
C23 C24 C25 121.9(3) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C20 C25 C24 120.9(3) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 O1 C18 119.2(3) . . ?
C20 S1 C19 102.48(14) . . ?
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
C1 C6 1.382(4) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.526(3) . ?
C7 C8 1.522(4) . ?
C7 C19 1.539(3) . ?
C7 H7 0.9800 . ?
C8 C17 1.377(4) . ?
C8 C9 1.429(3) . ?
C9 C10 1.413(4) . ?
C9 C14 1.427(4) . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.345(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.413(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(5) . ?
C15 C16 1.369(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(4) . ?
C16 H16 0.9300 . ?
C17 O1 1.377(3) . ?
C18 O1 1.408(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 S1 1.813(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.371(4) . ?
C20 C21 1.391(5) . ?
C20 S1 1.771(3) . ?
C21 C22 1.396(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(5) . ?
C23 C26 1.503(5) . ?
C24 C25 1.379(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C6 C1 C2 C3 1.0(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C2 C1 C6 C7 177.1(3) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C6 C7 -177.6(3) . . . . ?
C1 C6 C7 C8 73.5(3) . . . . ?
C5 C6 C7 C8 -107.9(3) . . . . ?
C1 C6 C7 C19 -156.1(3) . . . . ?
C5 C6 C7 C19 22.5(4) . . . . ?
C6 C7 C8 C17 69.8(3) . . . . ?
C19 C7 C8 C17 -60.2(3) . . . . ?
C6 C7 C8 C9 -106.4(3) . . . . ?
C19 C7 C8 C9 123.5(2) . . . . ?
C17 C8 C9 C10 -178.2(2) . . . . ?
C7 C8 C9 C10 -1.9(4) . . . . ?
C17 C8 C9 C14 0.6(3) . . . . ?
C7 C8 C9 C14 176.9(2) . . . . ?
C14 C9 C10 C11 -0.9(4) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 -178.2(3) . . . . ?
C12 C13 C14 C9 0.5(5) . . . . ?
C10 C9 C14 C15 178.9(2) . . . . ?
C8 C9 C14 C15 0.0(4) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C8 C9 C14 C13 -178.8(2) . . . . ?
C13 C14 C15 C16 179.1(3) . . . . ?
C9 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C9 C8 C17 O1 177.4(2) . . . . ?
C7 C8 C17 O1 1.0(3) . . . . ?
C9 C8 C17 C16 -1.4(4) . . . . ?
C7 C8 C17 C16 -177.8(3) . . . . ?
C15 C16 C17 C8 1.8(4) . . . . ?
C15 C16 C17 O1 -177.0(3) . . . . ?
C8 C7 C19 S1 -60.5(3) . . . . ?
C6 C7 C19 S1 170.7(2) . . . . ?
C25 C20 C21 C22 -1.5(4) . . . . ?
S1 C20 C21 C22 -179.9(2) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C21 C22 C23 C26 -179.6(3) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C26 C23 C24 C25 178.7(3) . . . . ?
C21 C20 C25 C24 0.6(4) . . . . ?
S1 C20 C25 C24 179.1(2) . . . . ?
C23 C24 C25 C20 0.6(5) . . . . ?
C8 C17 O1 C18 -177.4(3) . . . . ?
C16 C17 O1 C18 1.4(4) . . . . ?
C25 C20 S1 C19 125.6(2) . . . . ?
C21 C20 S1 C19 -56.0(3) . . . . ?
C7 C19 S1 C20 -63.0(3) . . . . ?
