#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/37/7123745.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_7123745
loop_
_publ_author_name
'Wu, Yan-Chen'
'Jiang, Shuai-Shuai'
'Luo, Shu-Zheng'
'Song, Ren-Jie'
'Li, Jin-Heng'
_publ_section_title
;
 Transition-Metal- and Oxidant-Free Directed Anodic C-H Sulfonylation of
 N,N-Disubstituted Anilines with Sulfinates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03789F
_journal_year                    2019
_chemical_formula_moiety         C15H16ClNO3S
_chemical_formula_sum            'C15 H16 Cl N O3 S'
_chemical_formula_weight         325.80
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-03-14 deposited with the CCDC.    2019-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.486(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.476(3)
_cell_length_b                   14.578(5)
_cell_length_c                   12.795(5)
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.67
_cell_volume                     1554.6(10)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10795
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.9334
_exptl_absorpt_correction_T_min  0.9264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+2.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.2222
_reflns_number_gt                1552
_reflns_number_total             2889
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc03789f2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7123745
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.12670(16) 0.27209(10) 0.86097(12) 0.0556(5) Uani 1 1 d .
O2 O -0.0051(4) 0.2640(3) 0.7725(3) 0.0742(12) Uani 1 1 d .
O3 O 0.1089(5) 0.3352(3) 0.9442(3) 0.0730(12) Uani 1 1 d .
N1 N 0.2775(5) 0.1711(3) 0.6968(4) 0.0554(12) Uani 1 1 d .
O1 O 0.6137(4) 0.4724(2) 0.8935(3) 0.0611(10) Uani 1 1 d .
C2 C 0.5413(6) 0.3968(3) 0.8431(4) 0.0429(12) Uani 1 1 d .
C4 C 0.3063(6) 0.3011(3) 0.8178(4) 0.0445(12) Uani 1 1 d .
C3 C 0.3918(6) 0.3761(3) 0.8661(4) 0.0447(12) Uani 1 1 d .
H3 H 0.3486 0.4122 0.9138 0.054 Uiso 1 1 calc R
C7 C 0.6062(6) 0.3412(4) 0.7756(4) 0.0516(13) Uani 1 1 d .
H7 H 0.7088 0.3527 0.7627 0.062 Uiso 1 1 calc R
C5 C 0.3689(6) 0.2466(3) 0.7447(4) 0.0448(12) Uani 1 1 d .
C6 C 0.5190(6) 0.2678(4) 0.7267(4) 0.0508(13) Uani 1 1 d .
H6 H 0.5639 0.2316 0.6799 0.061 Uiso 1 1 calc R
C1 C 0.7662(7) 0.4975(5) 0.8715(5) 0.0763(19) Uani 1 1 d .
H1A H 0.8414 0.4488 0.8928 0.114 Uiso 1 1 calc R
H1B H 0.8028 0.5523 0.9101 0.114 Uiso 1 1 calc R
H1C H 0.7575 0.5085 0.7967 0.114 Uiso 1 1 calc R
C8 C 0.1669(8) 0.1939(5) 0.5983(5) 0.087(2) Uani 1 1 d .
H8A H 0.1072 0.2480 0.6092 0.131 Uiso 1 1 calc R
H8B H 0.0942 0.1438 0.5785 0.131 Uiso 1 1 calc R
H8C H 0.2268 0.2050 0.5427 0.131 Uiso 1 1 calc R
C9 C 0.3697(9) 0.0905(5) 0.6818(7) 0.101(3) Uani 1 1 d .
H9A H 0.4267 0.1008 0.6246 0.151 Uiso 1 1 calc R
H9B H 0.2988 0.0391 0.6650 0.151 Uiso 1 1 calc R
H9C H 0.4449 0.0779 0.7459 0.151 Uiso 1 1 calc R
C10 C 0.1701(6) 0.1634(4) 0.9196(4) 0.0474(13) Uani 1 1 d .
C15 C 0.2754(6) 0.1595(4) 1.0162(4) 0.0555(14) Uani 1 1 d .
H15 H 0.3178 0.2132 1.0492 0.067 Uiso 1 1 calc R
C13 C 0.2521(8) -0.0028(4) 1.0123(5) 0.0657(16) Uani 1 1 d .
C11 C 0.1087(7) 0.0848(4) 0.8697(5) 0.0678(17) Uani 1 1 d .
H11 H 0.0401 0.0881 0.8042 0.081 Uiso 1 1 calc R
C14 C 0.3165(7) 0.0758(4) 1.0628(4) 0.0635(16) Uani 1 1 d .
H14 H 0.3869 0.0722 1.1275 0.076 Uiso 1 1 calc R
C12 C 0.1482(9) 0.0011(5) 0.9162(5) 0.0789(19) Uani 1 1 d .
H12 H 0.1053 -0.0525 0.8831 0.095 Uiso 1 1 calc R
Cl1 Cl 0.3008(3) -0.10800(13) 1.07183(15) 0.1029(7) 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O2 117.6(3)
O3 S1 C4 107.0(2)
O2 S1 C4 111.3(2)
O3 S1 C10 107.6(2)
O2 S1 C10 109.4(3)
C4 S1 C10 102.9(2)
C5 N1 C9 115.0(5)
C5 N1 C8 114.2(5)
C9 N1 C8 110.3(5)
C2 O1 C1 117.5(4)
O1 C2 C7 125.3(4)
O1 C2 C3 115.2(4)
C7 C2 C3 119.5(5)
C3 C4 C5 120.7(5)
C3 C4 S1 117.3(4)
C5 C4 S1 121.7(4)
C2 C3 C4 120.0(5)
C2 C3 H3 120.0
C4 C3 H3 120.0
C2 C7 C6 120.0(5)
C2 C7 H7 120.0
C6 C7 H7 120.0
C6 C5 C4 117.4(5)
C6 C5 N1 123.6(4)
C4 C5 N1 119.0(4)
C5 C6 C7 122.3(5)
C5 C6 H6 118.9
C7 C6 H6 118.9
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 120.7(5)
C11 C10 S1 121.5(4)
C15 C10 S1 117.8(4)
C14 C15 C10 119.6(5)
C14 C15 H15 120.2
C10 C15 H15 120.2
C12 C13 C14 121.3(6)
C12 C13 Cl1 119.5(5)
C14 C13 Cl1 119.2(5)
C10 C11 C12 120.1(5)
C10 C11 H11 120.0
C12 C11 H11 120.0
C15 C14 C13 119.1(5)
C15 C14 H14 120.4
C13 C14 H14 120.4
C11 C12 C13 119.2(6)
C11 C12 H12 120.4
C13 C12 H12 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.436(4)
S1 O2 1.443(4)
S1 C4 1.763(5)
S1 C10 1.764(6)
N1 C5 1.419(6)
N1 C9 1.444(7)
N1 C8 1.466(7)
O1 C2 1.364(6)
O1 C1 1.420(6)
C2 C7 1.371(7)
C2 C3 1.385(7)
C4 C3 1.393(7)
C4 C5 1.403(7)
C3 H3 0.9300
C7 C6 1.384(7)
C7 H7 0.9300
C5 C6 1.369(7)
C6 H6 0.9300
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.368(7)
C10 C15 1.387(7)
C15 C14 1.375(8)
C15 H15 0.9300
C13 C12 1.378(8)
C13 C14 1.378(8)
C13 Cl1 1.729(6)
C11 C12 1.372(8)
C11 H11 0.9300
C14 H14 0.9300
C12 H12 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
C1 O1 C2 C7 2.5(7)
C1 O1 C2 C3 -179.1(5)
O3 S1 C4 C3 -1.5(4)
O2 S1 C4 C3 128.1(4)
C10 S1 C4 C3 -114.8(4)
O3 S1 C4 C5 173.0(4)
O2 S1 C4 C5 -57.4(5)
C10 S1 C4 C5 59.7(4)
O1 C2 C3 C4 179.1(4)
C7 C2 C3 C4 -2.3(7)
C5 C4 C3 C2 -0.8(7)
S1 C4 C3 C2 173.8(3)
O1 C2 C7 C6 -178.2(5)
C3 C2 C7 C6 3.4(8)
C3 C4 C5 C6 2.7(7)
S1 C4 C5 C6 -171.6(4)
C3 C4 C5 N1 -179.6(4)
S1 C4 C5 N1 6.1(6)
C9 N1 C5 C6 35.5(8)
C8 N1 C5 C6 -93.4(6)
C9 N1 C5 C4 -142.0(6)
C8 N1 C5 C4 89.0(6)
C4 C5 C6 C7 -1.6(7)
N1 C5 C6 C7 -179.2(5)
C2 C7 C6 C5 -1.5(8)
O3 S1 C10 C11 142.3(4)
O2 S1 C10 C11 13.5(5)
C4 S1 C10 C11 -105.0(5)
O3 S1 C10 C15 -40.9(5)
O2 S1 C10 C15 -169.6(4)
C4 S1 C10 C15 71.9(4)
C11 C10 C15 C14 -0.9(8)
S1 C10 C15 C14 -177.8(4)
C15 C10 C11 C12 1.4(9)
S1 C10 C11 C12 178.2(5)
C10 C15 C14 C13 0.1(8)
C12 C13 C14 C15 0.3(9)
Cl1 C13 C14 C15 -178.9(4)
C10 C11 C12 C13 -1.1(10)
C14 C13 C12 C11 0.2(10)
Cl1 C13 C12 C11 179.4(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350804
