#------------------------------------------------------------------------------
#$Date: 2021-09-21 01:13:53 +0300 (Tue, 21 Sep 2021) $
#$Revision: 269217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564693.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_1564693
loop_
_publ_author_name
'Chen, Ya'
'Zhu, Kun'
'Huang, Qingqin'
'Lu, Yixin'
_publ_section_title
;
 Regiodivergent Sulfonylarylations of 1,3-Enynes via Nickel/Photoredox
 Dual Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04320J
_journal_year                    2021
_chemical_formula_sum            'C23 H16 Cl2 O3 S'
_chemical_formula_weight         443.32
_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
_atom_sites_solution_primary     'Dual Space'
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-12-27 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                97.717(2)
_cell_angle_beta                 95.887(2)
_cell_angle_gamma                105.087(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3445(5)
_cell_length_b                   7.5430(5)
_cell_length_c                   18.6349(12)
_cell_measurement_reflns_used    7685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.84
_cell_volume                     977.50(11)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_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_unetI/netI     0.0899
_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       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8693
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'Microfocus Sealed Tube'
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.862105
_exptl_absorpt_correction_T_min  0.702817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         8693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0639
_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)+(0.0455P)²+1.3720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6021
_reflns_number_total             8693
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04320j2.cif
_cod_data_source_block           K433
_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.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1564693
_shelx_shelxl_version_number     2016/6
_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.
;
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
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
C1 C 0.3147(6) 0.3960(5) 0.7887(2) 0.0250(9) Uani 1 1 d . . . . .
O1 O -0.0525(4) 0.2839(4) 0.74675(17) 0.0339(7) Uani 1 1 d . . . . .
Cl1 Cl 0.82280(18) 0.67834(18) 0.95735(7) 0.0438(3) Uani 1 1 d . . . . .
S1 S 0.12270(16) 0.31873(14) 0.71632(6) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.4947(6) 0.3899(6) 0.7734(2) 0.0292(10) Uani 1 1 d . . . . .
H2 H 0.510114 0.329453 0.727241 0.035 Uiso 1 1 calc R U . . .
O2 O 0.1548(4) 0.1722(4) 0.66625(16) 0.0323(7) Uani 1 1 d . . . . .
Cl2 Cl 0.75258(18) 1.17486(17) 0.93867(7) 0.0416(3) Uani 1 1 d . . . . .
C3 C 0.6516(6) 0.4734(6) 0.8267(2) 0.0321(10) Uani 1 1 d . . . . .
H3 H 0.775774 0.470126 0.817701 0.039 Uiso 1 1 calc R U . . .
O3 O 0.3210(4) 1.1564(4) 0.40401(17) 0.0334(7) Uani 1 1 d . . . . .
C4 C 0.6239(7) 0.5614(6) 0.8929(2) 0.0311(10) Uani 1 1 d . . . . .
C5 C 0.4461(6) 0.5613(6) 0.9095(2) 0.0280(9) Uani 1 1 d . . . . .
H5 H 0.430976 0.617450 0.956508 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2892(6) 0.4781(6) 0.8567(2) 0.0274(9) Uani 1 1 d . . . . .
H6 H 0.164943 0.477280 0.867007 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2642(6) 0.8111(5) 0.7705(2) 0.0265(9) Uani 1 1 d . . . . .
C8 C 0.4531(6) 0.8438(6) 0.7568(2) 0.0276(9) Uani 1 1 d . . . . .
H8 H 0.479425 0.786151 0.712050 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6018(6) 0.9588(6) 0.8075(2) 0.0309(10) Uani 1 1 d . . . . .
H9 H 0.729281 0.980868 0.797456 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5636(7) 1.0417(6) 0.8733(2) 0.0319(10) Uani 1 1 d . . . . .
C11 C 0.3791(7) 1.0157(6) 0.8878(2) 0.0324(10) Uani 1 1 d . . . . .
H11 H 0.353684 1.075226 0.932387 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2309(7) 0.9010(6) 0.8361(2) 0.0289(9) Uani 1 1 d . . . . .
H12 H 0.103498 0.883535 0.845835 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1055(6) 0.6818(6) 0.7173(2) 0.0281(9) Uani 1 1 d . . . . .
C14 C -0.0696(6) 0.7044(6) 0.7095(3) 0.0332(10) Uani 1 1 d . . . . .
H14A H -0.095882 0.805815 0.738542 0.040 Uiso 1 1 calc R U . . .
H14B H -0.167886 0.619008 0.674867 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1438(6) 0.5195(5) 0.6723(2) 0.0244(9) Uani 1 1 d . . . . .
C16 C 0.1859(6) 0.4997(5) 0.6043(2) 0.0242(9) Uani 1 1 d . . . . .
H16 H 0.199570 0.380590 0.586298 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2145(5) 0.6324(5) 0.5527(2) 0.0232(8) Uani 1 1 d . . . . .
C18 C 0.1774(6) 0.8076(5) 0.5640(2) 0.0259(9) Uani 1 1 d . . . . .
H18 H 0.126074 0.844779 0.606450 0.031 Uiso 1 1 calc R U . . .
C19 C 0.2160(6) 0.9247(5) 0.5134(2) 0.0263(9) Uani 1 1 d . . . . .
H19 H 0.190539 1.042441 0.521261 0.032 Uiso 1 1 calc R U . . .
C20 C 0.2918(6) 0.8734(6) 0.4508(2) 0.0252(9) Uani 1 1 d . . . . .
C21 C 0.3270(6) 0.6997(5) 0.4393(2) 0.0264(9) Uani 1 1 d . . . . .
H21 H 0.378646 0.662773 0.396887 0.032 Uiso 1 1 calc R U . . .
C22 C 0.2867(6) 0.5809(6) 0.4897(2) 0.0243(9) Uani 1 1 d . . . . .
H22 H 0.308921 0.461774 0.480908 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3395(6) 0.9995(6) 0.3974(2) 0.0277(9) Uani 1 1 d . . . . .
H23 H 0.387632 0.955608 0.355124 0.033 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'
Cl Cl 0.1484 0.1585 '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 121.1(4) . . ?
C6 C1 S1 120.4(3) . . ?
C2 C1 S1 118.1(3) . . ?
O2 S1 O1 118.52(19) . . ?
O2 S1 C1 109.04(19) . . ?
O1 S1 C1 108.68(19) . . ?
O2 S1 C15 108.55(18) . . ?
O1 S1 C15 108.20(19) . . ?
C1 S1 C15 102.70(19) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 Cl1 118.9(3) . . ?
C3 C4 Cl1 118.6(4) . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 117.8(4) . . ?
C12 C7 C13 121.3(4) . . ?
C8 C7 C13 120.9(4) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 Cl2 120.0(4) . . ?
C9 C10 Cl2 119.1(4) . . ?
C10 C11 C12 118.9(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 121.7(4) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
C14 C13 C7 122.2(4) . . ?
C14 C13 C15 119.4(4) . . ?
C7 C13 C15 118.3(4) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C13 129.9(4) . . ?
C16 C15 S1 115.5(3) . . ?
C13 C15 S1 114.5(3) . . ?
C15 C16 C17 130.4(4) . . ?
C15 C16 H16 114.8 . . ?
C17 C16 H16 114.8 . . ?
C22 C17 C18 118.8(4) . . ?
C22 C17 C16 116.8(4) . . ?
C18 C17 C16 124.4(4) . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 121.2(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.0(4) . . ?
C21 C20 C23 119.2(4) . . ?
C19 C20 C23 121.8(4) . . ?
C22 C21 C20 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 121.3(4) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
O3 C23 C20 124.1(4) . . ?
O3 C23 H23 118.0 . . ?
C20 C23 H23 118.0 . . ?
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 1.387(6) . ?
C1 C2 1.392(6) . ?
C1 S1 1.766(4) . ?
O1 S1 1.435(3) . ?
Cl1 C4 1.744(5) . ?
S1 O2 1.432(3) . ?
S1 C15 1.796(4) . ?
C2 C3 1.389(6) . ?
C2 H2 0.9500 . ?
Cl2 C10 1.737(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
O3 C23 1.218(5) . ?
C4 C5 1.373(6) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.393(6) . ?
C7 C8 1.400(6) . ?
C7 C13 1.484(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(6) . ?
C11 C12 1.390(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.337(6) . ?
C13 C15 1.494(6) . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 C16 1.334(6) . ?
C16 C17 1.471(5) . ?
C16 H16 0.9500 . ?
C17 C22 1.387(6) . ?
C17 C18 1.411(5) . ?
C18 C19 1.378(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(6) . ?
C20 C23 1.473(5) . ?
C21 C22 1.385(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
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 S1 O2 -154.2(3) . . . . ?
C2 C1 S1 O2 32.4(4) . . . . ?
C6 C1 S1 O1 -23.7(4) . . . . ?
C2 C1 S1 O1 162.9(3) . . . . ?
C6 C1 S1 C15 90.8(4) . . . . ?
C2 C1 S1 C15 -82.6(3) . . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
S1 C1 C2 C3 171.1(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C3 C4 C5 3.4(7) . . . . ?
C2 C3 C4 Cl1 -176.1(3) . . . . ?
C3 C4 C5 C6 -3.3(6) . . . . ?
Cl1 C4 C5 C6 176.2(3) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C2 C1 C6 C5 2.3(6) . . . . ?
S1 C1 C6 C5 -170.9(3) . . . . ?
C12 C7 C8 C9 1.3(6) . . . . ?
C13 C7 C8 C9 -177.6(4) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C8 C9 C10 C11 -2.0(6) . . . . ?
C8 C9 C10 Cl2 176.3(3) . . . . ?
C9 C10 C11 C12 1.5(6) . . . . ?
Cl2 C10 C11 C12 -176.8(3) . . . . ?
C10 C11 C12 C7 0.4(6) . . . . ?
C8 C7 C12 C11 -1.8(6) . . . . ?
C13 C7 C12 C11 177.1(4) . . . . ?
C12 C7 C13 C14 31.4(6) . . . . ?
C8 C7 C13 C14 -149.7(4) . . . . ?
C12 C7 C13 C15 -147.3(4) . . . . ?
C8 C7 C13 C15 31.5(5) . . . . ?
C14 C13 C15 C16 84.1(6) . . . . ?
C7 C13 C15 C16 -97.2(5) . . . . ?
C14 C13 C15 S1 -93.9(4) . . . . ?
C7 C13 C15 S1 84.8(4) . . . . ?
O2 S1 C15 C16 -0.7(4) . . . . ?
O1 S1 C15 C16 -130.6(3) . . . . ?
C1 S1 C15 C16 114.6(3) . . . . ?
O2 S1 C15 C13 177.6(3) . . . . ?
O1 S1 C15 C13 47.7(3) . . . . ?
C1 S1 C15 C13 -67.1(3) . . . . ?
C13 C15 C16 C17 2.3(8) . . . . ?
S1 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C17 C22 170.1(4) . . . . ?
C15 C16 C17 C18 -8.5(7) . . . . ?
C22 C17 C18 C19 -1.0(6) . . . . ?
C16 C17 C18 C19 177.5(4) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C18 C19 C20 C23 -178.0(4) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C23 C20 C21 C22 178.7(4) . . . . ?
C20 C21 C22 C17 -1.2(6) . . . . ?
C18 C17 C22 C21 1.7(6) . . . . ?
C16 C17 C22 C21 -177.0(4) . . . . ?
C21 C20 C23 O3 -177.0(4) . . . . ?
C19 C20 C23 O3 1.6(7) . . . . ?
