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#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/60/7126004.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_7126004
loop_
_publ_author_name
'Zhang, Jun'
'Yang, Min'
'Liu, Jin-Biao'
'He, Fu-Sheng'
'Wu, Jie'
_publ_section_title
;
 A copper-catalyzed insertion of sulfur dioxide via radical coupling.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3225
_journal_page_last               3228
_journal_paper_doi               10.1039/d0cc00375a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C22 H19 Cl N2 O2 S'
_chemical_formula_weight         410.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-11-13 deposited with the CCDC.	2020-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.581(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7878(2)
_cell_length_b                   22.1588(9)
_cell_length_c                   13.8692(5)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.61
_cell_measurement_theta_min      3.29
_cell_volume                     2072.31(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(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           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19378
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.989
_diffrn_reflns_theta_min         4.455
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0412
_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)+(0.0569P)²+0.6365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3806
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00375a2.cif
_cod_data_source_block           ga_90329a_a
_cod_depositor_comments          'Adding full bibliography for 7126004.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126004
_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. 
;
_shelx_estimated_absorpt_t_min   0.840
_shelx_estimated_absorpt_t_max   0.900
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.35864(6) 0.30779(2) 0.39676(3) 0.04203(13) Uani 1 1 d . . . . .
Cl1 Cl 1.00757(9) 0.10748(3) 0.21968(5) 0.0873(2) Uani 1 1 d . . . . .
N1 N 0.3452(4) 0.26275(10) 0.60983(14) 0.0734(6) Uani 1 1 d . . . . .
H1A H 0.275(5) 0.2944(14) 0.589(2) 0.091(9) Uiso 1 1 d . . . . .
H1B H 0.346(4) 0.2495(11) 0.665(2) 0.067(7) Uiso 1 1 d . . . . .
N2 N 0.6623(4) 0.52677(10) 0.38301(18) 0.0921(7) Uani 1 1 d . . . . .
O1 O 0.2869(2) 0.29034(6) 0.29890(9) 0.0553(3) Uani 1 1 d . . . . .
O2 O 0.2152(2) 0.33353(6) 0.45402(10) 0.0572(3) Uani 1 1 d . . . . .
C1 C 0.4575(3) 0.23371(8) 0.55176(13) 0.0474(4) Uani 1 1 d . . . . .
C2 C 0.4757(2) 0.24680(7) 0.45701(12) 0.0412(3) Uani 1 1 d . . . . .
C3 C 0.5711(3) 0.18089(8) 0.59784(12) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.4829(3) 0.12310(8) 0.59316(13) 0.0486(4) Uani 1 1 d . . . . .
C5 C 0.2876(3) 0.11277(9) 0.54779(16) 0.0594(5) Uani 1 1 d . . . . .
H5 H 0.212574 0.144544 0.519316 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2110(4) 0.05599(11) 0.5463(2) 0.0854(8) Uani 1 1 d . . . . .
H6 H 0.083484 0.049480 0.515831 0.103 Uiso 1 1 calc R U . . .
C7 C 0.3175(5) 0.00739(12) 0.5889(2) 0.0945(9) Uani 1 1 d . . . . .
H7 H 0.261186 -0.030913 0.587178 0.113 Uiso 1 1 calc R U . . .
C8 C 0.5032(4) 0.01623(11) 0.63284(19) 0.0743(6) Uani 1 1 d . . . . .
H8 H 0.573288 -0.016474 0.661327 0.089 Uiso 1 1 calc R U . . .
C9 C 0.5945(3) 0.07381(9) 0.63687(14) 0.0533(4) Uani 1 1 d . . . . .
C10 C 0.7870(3) 0.08278(11) 0.68175(16) 0.0649(5) Uani 1 1 d . . . . .
H10 H 0.860425 0.050277 0.708819 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8679(3) 0.13960(12) 0.68589(17) 0.0724(6) Uani 1 1 d . . . . .
H11 H 0.995762 0.145726 0.716268 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7573(3) 0.18851(10) 0.64413(15) 0.0579(5) Uani 1 1 d . . . . .
H12 H 0.812513 0.226960 0.648225 0.069 Uiso 1 1 calc R U . . .
C13 C 0.5453(3) 0.36236(8) 0.38574(14) 0.0528(4) Uani 1 1 d . . . . .
H13A H 0.643215 0.345354 0.347812 0.063 Uiso 1 1 calc R U . . .
H13B H 0.486049 0.396910 0.350546 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6485(4) 0.38356(9) 0.48198(16) 0.0624(5) Uani 1 1 d . . . . .
H14A H 0.708492 0.349259 0.517552 0.075 Uiso 1 1 calc R U . . .
H14B H 0.551684 0.401112 0.520033 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8094(4) 0.43056(11) 0.4682(2) 0.0776(7) Uani 1 1 d . . . . .
H15A H 0.878297 0.441128 0.531090 0.093 Uiso 1 1 calc R U . . .
H15B H 0.905366 0.412982 0.429705 0.093 Uiso 1 1 calc R U . . .
C16 C 0.7277(4) 0.48501(10) 0.42052(18) 0.0679(6) Uani 1 1 d . . . . .
C17 C 0.6069(2) 0.21150(7) 0.39824(11) 0.0397(3) Uani 1 1 d . . . . .
C18 C 0.8077(3) 0.22394(9) 0.40302(15) 0.0537(4) Uani 1 1 d . . . . .
H18 H 0.861394 0.254403 0.444075 0.064 Uiso 1 1 calc R U . . .
C19 C 0.9300(3) 0.19227(9) 0.34837(16) 0.0590(5) Uani 1 1 d . . . . .
H19 H 1.064684 0.201065 0.352719 0.071 Uiso 1 1 calc R U . . .
C20 C 0.8503(3) 0.14759(9) 0.28750(14) 0.0513(4) Uani 1 1 d . . . . .
C21 C 0.6520(3) 0.13405(8) 0.27973(15) 0.0534(4) Uani 1 1 d . . . . .
H21 H 0.599454 0.103874 0.237799 0.064 Uiso 1 1 calc R U . . .
C22 C 0.5313(3) 0.16617(8) 0.33554(14) 0.0483(4) Uani 1 1 d . . . . .
H22 H 0.396712 0.157154 0.330862 0.058 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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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
O1 S1 O2 116.61(8) . . ?
O1 S1 C2 109.36(8) . . ?
O2 S1 C2 110.11(8) . . ?
O1 S1 C13 105.65(9) . . ?
O2 S1 C13 108.20(9) . . ?
C2 S1 C13 106.33(9) . . ?
C1 N1 H1A 120.5(19) . . ?
C1 N1 H1B 116.8(17) . . ?
H1A N1 H1B 123(3) . . ?
N1 C1 C2 126.78(18) . . ?
N1 C1 C3 114.77(16) . . ?
C2 C1 C3 118.45(15) . . ?
C1 C2 C17 122.59(15) . . ?
C1 C2 S1 122.89(13) . . ?
C17 C2 S1 114.45(11) . . ?
C12 C3 C4 119.99(18) . . ?
C12 C3 C1 120.49(17) . . ?
C4 C3 C1 119.52(16) . . ?
C3 C4 C5 122.42(17) . . ?
C3 C4 C9 118.31(17) . . ?
C5 C4 C9 119.27(17) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 C4 120.36(19) . . ?
C8 C9 C4 117.7(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C3 C12 C11 121.50(19) . . ?
C3 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 S1 113.60(14) . . ?
C14 C13 H13A 108.8 . . ?
S1 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
S1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 111.42(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.3(2) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C15 179.1(3) . . ?
C18 C17 C22 117.75(15) . . ?
C18 C17 C2 120.95(15) . . ?
C22 C17 C2 121.28(15) . . ?
C19 C18 C17 121.57(17) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 119.08(17) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.40(16) . . ?
C21 C20 Cl1 120.13(14) . . ?
C19 C20 Cl1 118.47(15) . . ?
C20 C21 C22 118.77(17) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C21 C22 C17 121.42(16) . . ?
C21 C22 H22 119.3 . . ?
C17 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 O1 1.4412(13) . ?
S1 O2 1.4426(13) . ?
S1 C2 1.7331(17) . ?
S1 C13 1.7706(19) . ?
Cl1 C20 1.7450(18) . ?
N1 C1 1.336(2) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.82(3) . ?
N2 C16 1.127(3) . ?
C1 C2 1.365(2) . ?
C1 C3 1.503(3) . ?
C2 C17 1.496(2) . ?
C3 C12 1.361(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.420(3) . ?
C4 C9 1.424(3) . ?
C5 C6 1.360(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.537(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.455(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.385(2) . ?
C17 C22 1.388(2) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.82(3) 2.13(3) 2.942(2) 168(2) 4_566
N1 H1A O2 0.88(3) 2.06(3) 2.733(3) 133(3) .
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
N1 C1 C2 C17 179.7(2) . . . . ?
C3 C1 C2 C17 -1.3(3) . . . . ?
N1 C1 C2 S1 3.0(3) . . . . ?
C3 C1 C2 S1 -177.97(13) . . . . ?
O1 S1 C2 C1 -140.51(15) . . . . ?
O2 S1 C2 C1 -11.14(18) . . . . ?
C13 S1 C2 C1 105.85(16) . . . . ?
O1 S1 C2 C17 42.54(14) . . . . ?
O2 S1 C2 C17 171.91(12) . . . . ?
C13 S1 C2 C17 -71.10(14) . . . . ?
N1 C1 C3 C12 -90.5(2) . . . . ?
C2 C1 C3 C12 90.4(2) . . . . ?
N1 C1 C3 C4 89.3(2) . . . . ?
C2 C1 C3 C4 -89.9(2) . . . . ?
C12 C3 C4 C5 178.52(19) . . . . ?
C1 C3 C4 C5 -1.2(3) . . . . ?
C12 C3 C4 C9 -0.7(3) . . . . ?
C1 C3 C4 C9 179.57(15) . . . . ?
C3 C4 C5 C6 -179.6(2) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C3 C4 C9 C10 -0.9(3) . . . . ?
C5 C4 C9 C10 179.86(19) . . . . ?
C3 C4 C9 C8 179.12(19) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C8 C9 C10 C11 -178.5(2) . . . . ?
C4 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C4 C3 C12 C11 1.7(3) . . . . ?
C1 C3 C12 C11 -178.58(19) . . . . ?
C10 C11 C12 C3 -1.0(3) . . . . ?
O1 S1 C13 C14 -176.37(15) . . . . ?
O2 S1 C13 C14 58.05(17) . . . . ?
C2 S1 C13 C14 -60.21(17) . . . . ?
S1 C13 C14 C15 179.73(16) . . . . ?
C13 C14 C15 C16 62.6(3) . . . . ?
C1 C2 C17 C18 -83.4(2) . . . . ?
S1 C2 C17 C18 93.61(18) . . . . ?
C1 C2 C17 C22 98.1(2) . . . . ?
S1 C2 C17 C22 -84.91(18) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C2 C17 C18 C19 -179.19(18) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C18 C19 C20 Cl1 -179.43(17) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
Cl1 C20 C21 C22 179.14(15) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C18 C17 C22 C21 0.3(3) . . . . ?
C2 C17 C22 C21 178.89(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351736
