#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:58:20 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/07/1570764.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_1570764
loop_
_publ_author_name
'Shi, Zhaojiang'
'Dong, Shicheng'
'Liu, Ting'
'Wang, Wei-Zhen'
'Li, Nan'
'Yuan, Yaofeng'
'Zhu, Jun'
'Ye, Ke-Yin'
_publ_section_title
;
 Electrochemical cascade migratory versus ortho-cyclization of
 2-alkynylbenzenesulfonamides.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2827
_journal_page_last               2832
_journal_paper_doi               10.1039/d3sc05229j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C22 H15 N O3 S'
_chemical_formula_sum            'C22 H15 N O3 S'
_chemical_formula_weight         373.41
_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
_audit_creation_date             2021-08-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-06-24 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                115.736(4)
_cell_angle_beta                 95.407(4)
_cell_angle_gamma                101.180(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9567(12)
_cell_length_b                   10.1290(13)
_cell_length_c                   11.0747(14)
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.828
_cell_measurement_theta_min      2.286
_cell_volume                     869.6(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.084
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.8592.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0456
_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)+(0.0527P)²+0.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2406
_reflns_number_total             3065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05229j2.cif
_cod_data_source_block           szj-065t-1-1
_cod_depositor_comments
'Adding full bibliography for 1570763--1570767.cif.'
_cod_database_code               1570764
_shelx_shelxl_version_number     2018/3
_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   0.902
_shelx_estimated_absorpt_t_min   0.867
_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:
 C10(H00B), C11(H00E), C13(H00F), C5(H00H), C19(H00J), C17(H00K), C4(H00L),
 C21(H00M), C18(H00N), C20(H00O), C3(H00P), C2(H00R)
2.b Idealised Me refined as rotating group:
 C22(H00A,H00C,H00D)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.34958(7) 0.19796(7) 0.50220(6) 0.0295(2) Uani 1 1 d . . . . .
O3 O 0.3042(2) 0.4798(2) 0.69677(17) 0.0365(5) Uani 1 1 d . . . . .
O1 O 0.2254(2) 0.1244(2) 0.54134(18) 0.0371(5) Uani 1 1 d . . . . .
O2 O 0.5002(2) 0.2563(2) 0.58700(19) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.2970(2) 0.3348(2) 0.47233(19) 0.0269(5) Uani 1 1 d . . . . .
C16 C 0.1961(3) 0.3729(3) 0.1519(2) 0.0223(5) Uani 1 1 d . . . . .
C9 C 0.1896(3) 0.5330(3) 0.4014(2) 0.0243(5) Uani 1 1 d . . . . .
C8 C 0.2205(3) 0.3977(3) 0.2959(2) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.2191(3) 0.5657(3) 0.5394(2) 0.0256(5) Uani 1 1 d . . . . .
C6 C 0.3104(3) 0.1584(3) 0.2519(2) 0.0274(6) Uani 1 1 d . . . . .
C10 C 0.1324(3) 0.6364(3) 0.3702(2) 0.0261(5) Uani 1 1 d . . . . .
H00B H 0.110953 0.617446 0.279538 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2760(3) 0.4623(3) 0.5805(2) 0.0279(6) Uani 1 1 d . . . . .
C7 C 0.2718(3) 0.3020(3) 0.3326(2) 0.0250(5) Uani 1 1 d . . . . .
C11 C 0.1072(3) 0.7648(3) 0.4706(2) 0.0294(6) Uani 1 1 d . . . . .
H00E H 0.068689 0.830927 0.446663 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1937(3) 0.6959(3) 0.6393(2) 0.0299(6) Uani 1 1 d . . . . .
H00F H 0.214545 0.714913 0.730053 0.036 Uiso 1 1 calc R U . . .
C1 C 0.3551(3) 0.0912(3) 0.3309(3) 0.0294(6) Uani 1 1 d . . . . .
C5 C 0.3070(3) 0.0828(3) 0.1119(3) 0.0305(6) Uani 1 1 d . . . . .
H00H H 0.276638 0.122439 0.054835 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1390(3) 0.7980(3) 0.6098(3) 0.0299(6) Uani 1 1 d . . . . .
C19 C 0.1485(3) 0.3353(3) -0.1139(2) 0.0308(6) Uani 1 1 d . . . . .
H00J H 0.132923 0.322367 -0.203041 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0513(3) 0.3018(3) 0.0672(3) 0.0342(6) Uani 1 1 d . . . . .
H00K H -0.031550 0.266155 0.099291 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3498(3) -0.0524(3) 0.0597(3) 0.0360(6) Uani 1 1 d . . . . .
H00L H 0.348014 -0.102669 -0.033677 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3170(3) 0.4265(3) 0.1027(3) 0.0364(7) Uani 1 1 d . . . . .
H00M H 0.415187 0.475767 0.158634 0.044 Uiso 1 1 calc R U . . .
C18 C 0.0283(3) 0.2832(3) -0.0651(3) 0.0383(7) Uani 1 1 d . . . . .
H00N H -0.069874 0.234877 -0.121251 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2922(3) 0.4068(3) -0.0300(3) 0.0399(7) Uani 1 1 d . . . . .
H00O H 0.374384 0.442716 -0.062610 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3950(3) -0.1157(3) 0.1407(3) 0.0406(7) Uani 1 1 d . . . . .
H00P H 0.423808 -0.206396 0.101946 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1140(3) 0.9408(3) 0.7181(3) 0.0383(7) Uani 1 1 d . . . . .
H00A H 0.208530 1.020546 0.751657 0.057 Uiso 1 1 calc R U . . .
H00C H 0.084367 0.923485 0.792163 0.057 Uiso 1 1 calc R U . . .
H00D H 0.033243 0.969812 0.679923 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3972(3) -0.0442(3) 0.2781(3) 0.0375(7) Uani 1 1 d . . . . .
H00R H 0.426033 -0.085424 0.334209 0.045 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'
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
O1 S1 N1 109.49(11) . . ?
O1 S1 C1 111.51(11) . . ?
O2 S1 O1 118.77(11) . . ?
O2 S1 N1 110.20(11) . . ?
O2 S1 C1 111.63(12) . . ?
N1 S1 C1 91.99(11) . . ?
C15 N1 S1 119.60(16) . . ?
C15 N1 C7 125.9(2) . . ?
C7 N1 S1 114.47(16) . . ?
C17 C16 C8 120.8(2) . . ?
C17 C16 C21 118.7(2) . . ?
C21 C16 C8 120.4(2) . . ?
C14 C9 C8 120.7(2) . . ?
C14 C9 C10 117.2(2) . . ?
C10 C9 C8 122.0(2) . . ?
C9 C8 C16 118.6(2) . . ?
C7 C8 C16 122.5(2) . . ?
C7 C8 C9 118.9(2) . . ?
C9 C14 C15 120.8(2) . . ?
C13 C14 C9 120.5(2) . . ?
C13 C14 C15 118.7(2) . . ?
C1 C6 C7 113.0(2) . . ?
C5 C6 C7 129.5(2) . . ?
C5 C6 C1 117.5(2) . . ?
C9 C10 H00B 119.3 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H00B 119.3 . . ?
O3 C15 N1 120.0(2) . . ?
O3 C15 C14 125.9(2) . . ?
N1 C15 C14 114.1(2) . . ?
N1 C7 C6 108.7(2) . . ?
C8 C7 N1 119.6(2) . . ?
C8 C7 C6 131.6(2) . . ?
C10 C11 H00E 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C12 C11 H00E 119.5 . . ?
C14 C13 H00F 118.7 . . ?
C12 C13 C14 122.6(2) . . ?
C12 C13 H00F 118.7 . . ?
C6 C1 S1 111.65(19) . . ?
C2 C1 S1 124.7(2) . . ?
C2 C1 C6 123.7(2) . . ?
C6 C5 H00H 120.7 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H00H 120.7 . . ?
C11 C12 C22 120.1(2) . . ?
C13 C12 C11 117.2(2) . . ?
C13 C12 C22 122.7(2) . . ?
C18 C19 H00J 120.4 . . ?
C18 C19 C20 119.1(2) . . ?
C20 C19 H00J 120.4 . . ?
C16 C17 H00K 119.7 . . ?
C16 C17 C18 120.6(2) . . ?
C18 C17 H00K 119.7 . . ?
C5 C4 H00L 118.7 . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 H00L 118.7 . . ?
C16 C21 H00M 120.0 . . ?
C16 C21 C20 120.0(2) . . ?
C20 C21 H00M 120.0 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H00N 119.7 . . ?
C17 C18 H00N 119.7 . . ?
C19 C20 C21 121.0(2) . . ?
C19 C20 H00O 119.5 . . ?
C21 C20 H00O 119.5 . . ?
C4 C3 H00P 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H00P 120.2 . . ?
C12 C22 H00A 109.5 . . ?
C12 C22 H00C 109.5 . . ?
C12 C22 H00D 109.5 . . ?
H00A C22 H00C 109.5 . . ?
H00A C22 H00D 109.5 . . ?
H00C C22 H00D 109.5 . . ?
C1 C2 H00R 121.0 . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H00R 121.0 . . ?
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
S1 O1 1.4247(18) . ?
S1 O2 1.4217(18) . ?
S1 N1 1.695(2) . ?
S1 C1 1.740(3) . ?
O3 C15 1.215(3) . ?
N1 C15 1.390(3) . ?
N1 C7 1.420(3) . ?
C16 C8 1.490(3) . ?
C16 C17 1.380(3) . ?
C16 C21 1.380(3) . ?
C9 C8 1.462(3) . ?
C9 C14 1.402(3) . ?
C9 C10 1.403(3) . ?
C8 C7 1.339(3) . ?
C14 C15 1.462(3) . ?
C14 C13 1.383(3) . ?
C6 C7 1.469(3) . ?
C6 C1 1.394(4) . ?
C6 C5 1.394(3) . ?
C10 H00B 0.9300 . ?
C10 C11 1.372(3) . ?
C11 H00E 0.9300 . ?
C11 C12 1.414(3) . ?
C13 H00F 0.9300 . ?
C13 C12 1.370(4) . ?
C1 C2 1.382(4) . ?
C5 H00H 0.9300 . ?
C5 C4 1.383(4) . ?
C12 C22 1.500(3) . ?
C19 H00J 0.9300 . ?
C19 C18 1.367(4) . ?
C19 C20 1.369(4) . ?
C17 H00K 0.9300 . ?
C17 C18 1.383(3) . ?
C4 H00L 0.9300 . ?
C4 C3 1.383(4) . ?
C21 H00M 0.9300 . ?
C21 C20 1.384(3) . ?
C18 H00N 0.9300 . ?
C20 H00O 0.9300 . ?
C3 H00P 0.9300 . ?
C3 C2 1.369(4) . ?
C22 H00A 0.9600 . ?
C22 H00C 0.9600 . ?
C22 H00D 0.9600 . ?
C2 H00R 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
S1 N1 C15 O3 4.5(3) . . . . ?
S1 N1 C15 C14 -175.46(16) . . . . ?
S1 N1 C7 C8 175.88(18) . . . . ?
S1 N1 C7 C6 -4.0(2) . . . . ?
S1 C1 C2 C3 179.61(19) . . . . ?
O1 S1 N1 C15 67.5(2) . . . . ?
O1 S1 N1 C7 -109.81(17) . . . . ?
O1 S1 C1 C6 109.36(19) . . . . ?
O1 S1 C1 C2 -70.1(2) . . . . ?
O2 S1 N1 C15 -64.9(2) . . . . ?
O2 S1 N1 C7 117.79(17) . . . . ?
O2 S1 C1 C6 -115.18(18) . . . . ?
O2 S1 C1 C2 65.3(2) . . . . ?
N1 S1 C1 C6 -2.51(19) . . . . ?
N1 S1 C1 C2 178.0(2) . . . . ?
C16 C8 C7 N1 178.1(2) . . . . ?
C16 C8 C7 C6 -2.0(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C16 C21 C20 C19 0.4(5) . . . . ?
C9 C8 C7 N1 -0.9(3) . . . . ?
C9 C8 C7 C6 179.0(2) . . . . ?
C9 C14 C15 O3 -179.6(2) . . . . ?
C9 C14 C15 N1 0.3(3) . . . . ?
C9 C14 C13 C12 0.2(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C8 C16 C17 C18 178.1(3) . . . . ?
C8 C16 C21 C20 -178.1(3) . . . . ?
C8 C9 C14 C15 -2.3(3) . . . . ?
C8 C9 C14 C13 178.2(2) . . . . ?
C8 C9 C10 C11 -178.5(2) . . . . ?
C14 C9 C8 C16 -176.4(2) . . . . ?
C14 C9 C8 C7 2.6(3) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C14 C13 C12 C11 0.6(4) . . . . ?
C14 C13 C12 C22 -178.9(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C10 C9 C8 C16 2.5(3) . . . . ?
C10 C9 C8 C7 -178.5(2) . . . . ?
C10 C9 C14 C15 178.8(2) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 C22 178.6(2) . . . . ?
C15 N1 C7 C8 -1.2(3) . . . . ?
C15 N1 C7 C6 178.8(2) . . . . ?
C15 C14 C13 C12 -179.3(2) . . . . ?
C7 N1 C15 O3 -178.6(2) . . . . ?
C7 N1 C15 C14 1.5(3) . . . . ?
C7 C6 C1 S1 0.6(3) . . . . ?
C7 C6 C1 C2 -179.9(2) . . . . ?
C7 C6 C5 C4 179.8(2) . . . . ?
C13 C14 C15 O3 -0.1(4) . . . . ?
C13 C14 C15 N1 179.8(2) . . . . ?
C1 S1 N1 C15 -178.83(19) . . . . ?
C1 S1 N1 C7 3.86(18) . . . . ?
C1 C6 C7 N1 2.1(3) . . . . ?
C1 C6 C7 C8 -177.8(2) . . . . ?
C1 C6 C5 C4 -0.8(3) . . . . ?
C5 C6 C7 N1 -178.5(2) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C5 C6 C1 S1 -178.86(18) . . . . ?
C5 C6 C1 C2 0.6(4) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C17 C16 C8 C9 -85.6(3) . . . . ?
C17 C16 C8 C7 95.5(3) . . . . ?
C17 C16 C21 C20 -0.8(4) . . . . ?
C4 C3 C2 C1 -0.8(4) . . . . ?
C21 C16 C8 C9 91.8(3) . . . . ?
C21 C16 C8 C7 -87.2(3) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C20 C19 C18 C17 -0.3(4) . . . . ?
