#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:58:20 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/07/1570767.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_1570767
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         'C21 H13 N O4 S'
_chemical_formula_sum            'C21 H13 N O4 S'
_chemical_formula_weight         375.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-25
_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                90
_cell_angle_beta                 94.504(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.086(3)
_cell_length_b                   5.5939(14)
_cell_length_c                   38.073(11)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.578
_cell_measurement_theta_min      2.542
_cell_volume                     1716.8(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1153
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            31689
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.206
_diffrn_reflns_theta_max         25.206
_diffrn_reflns_theta_min         2.146
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4477
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.6008.
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    1.452
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0513
_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)+(0.0459P)²+0.3529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             3082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05229j2.cif
_cod_data_source_block           szj-078x
_cod_depositor_comments
'Adding full bibliography for 1570763--1570767.cif.'
_cod_original_cell_volume        1716.7(9)
_cod_database_code               1570767
_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   0.979
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
S001 S 0.18994(11) 0.95585(13) 0.30430(2) 0.0604(3) Uani 1 1 d . . . . .
O002 O -0.0736(3) 0.9393(4) 0.36337(5) 0.0678(6) Uani 1 1 d . . . . .
O003 O 0.0719(3) 0.8584(4) 0.27869(5) 0.0762(7) Uani 1 1 d . . . . .
O004 O -0.1515(3) 0.6621(4) 0.48592(6) 0.0793(7) Uani 1 1 d . . . . .
O005 O 0.1908(3) 1.2081(3) 0.30923(5) 0.0811(7) Uani 1 1 d . . . . .
N006 N 0.1737(3) 0.8192(4) 0.34286(6) 0.0517(6) Uani 1 1 d . . . . .
C007 C 0.3874(3) 0.4019(4) 0.40707(6) 0.0376(6) Uani 1 1 d . . . . .
C008 C 0.4689(3) 0.2194(4) 0.39053(7) 0.0441(7) Uani 1 1 d . . . . .
H008 H 0.459851 0.209478 0.366072 0.053 Uiso 1 1 calc R U . . .
C009 C 0.2851(3) 0.5779(4) 0.38657(6) 0.0375(6) Uani 1 1 d . . . . .
C00A C 0.1215(3) 0.6755(4) 0.39859(6) 0.0406(7) Uani 1 1 d . . . . .
C00B C 0.1464(3) 0.8474(4) 0.42869(7) 0.0431(7) Uani 1 1 d . . . . .
H00B H 0.227713 0.964237 0.427645 0.052 Uiso 1 1 calc R U . . .
C00C C 0.3990(3) 0.4056(4) 0.44381(6) 0.0443(7) Uani 1 1 d . . . . .
H00C H 0.343201 0.523003 0.455520 0.053 Uiso 1 1 calc R U . . .
C00D C 0.3108(3) 0.6728(4) 0.35501(7) 0.0433(7) Uani 1 1 d . . . . .
C00E C 0.0540(4) 0.8295(5) 0.36662(7) 0.0499(8) Uani 1 1 d . . . . .
C00F C 0.4378(4) 0.6894(5) 0.32975(7) 0.0482(7) Uani 1 1 d . . . . .
C00G C -0.0009(3) 0.4841(5) 0.40507(8) 0.0511(8) Uani 1 1 d . . . . .
H00G H -0.018897 0.363273 0.388426 0.061 Uiso 1 1 calc R U . . .
C00H C 0.0600(4) 0.8423(5) 0.45648(7) 0.0510(7) Uani 1 1 d . . . . .
H00H H 0.079640 0.957892 0.473866 0.061 Uiso 1 1 calc R U . . .
C00I C -0.0653(4) 0.6615(5) 0.46077(8) 0.0539(8) Uani 1 1 d . . . . .
C00J C 0.4920(3) 0.2379(5) 0.46291(7) 0.0527(8) Uani 1 1 d . . . . .
H00J H 0.499379 0.243288 0.487401 0.063 Uiso 1 1 calc R U . . .
C00K C 0.5628(3) 0.0535(5) 0.40991(8) 0.0516(7) Uani 1 1 d . . . . .
H00K H 0.618860 -0.065049 0.398497 0.062 Uiso 1 1 calc R U . . .
C00L C 0.5740(4) 0.0627(5) 0.44604(8) 0.0556(8) Uani 1 1 d . . . . .
H00L H 0.637164 -0.049955 0.459079 0.067 Uiso 1 1 calc R U . . .
C00M C 0.3884(4) 0.8369(5) 0.30161(7) 0.0548(8) Uani 1 1 d . . . . .
C00N C 0.5964(4) 0.5925(5) 0.33122(7) 0.0568(8) Uani 1 1 d . . . . .
H00N H 0.633955 0.495509 0.350033 0.068 Uiso 1 1 calc R U . . .
C00O C 0.6973(4) 0.6406(6) 0.30479(8) 0.0684(9) Uani 1 1 d . . . . .
H00O H 0.803240 0.574782 0.305801 0.082 Uiso 1 1 calc R U . . .
C00P C -0.0851(4) 0.4791(5) 0.43362(9) 0.0613(9) Uani 1 1 d . . . . .
H00P H -0.159293 0.354671 0.436322 0.074 Uiso 1 1 calc R U . . .
C00Q C 0.4908(5) 0.8853(6) 0.27452(8) 0.0767(11) Uani 1 1 d . . . . .
H00Q H 0.455588 0.982758 0.255600 0.092 Uiso 1 1 calc R U . . .
C00R C 0.6453(5) 0.7830(7) 0.27705(9) 0.0823(11) Uani 1 1 d . . . . .
H00R H 0.716272 0.811446 0.259438 0.099 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
O003 S001 O005 117.87(13) . . ?
O003 S001 N006 109.46(13) . . ?
O003 S001 C00M 112.64(14) . . ?
O005 S001 N006 109.73(12) . . ?
O005 S001 C00M 112.97(14) . . ?
N006 S001 C00M 90.77(13) . . ?
C00D N006 S001 115.8(2) . . ?
C00E N006 S001 131.8(2) . . ?
C00E N006 C00D 112.3(2) . . ?
C008 C007 C009 121.2(2) . . ?
C008 C007 C00C 117.9(2) . . ?
C00C C007 C009 120.9(2) . . ?
C007 C008 H008 119.6 . . ?
C00K C008 C007 120.9(2) . . ?
C00K C008 H008 119.6 . . ?
C007 C009 C00A 122.8(2) . . ?
C00D C009 C007 128.3(2) . . ?
C00D C009 C00A 108.9(2) . . ?
C009 C00A C00E 102.8(2) . . ?
C00B C00A C009 112.9(2) . . ?
C00B C00A C00E 105.14(19) . . ?
C00G C00A C009 113.1(2) . . ?
C00G C00A C00B 112.7(2) . . ?
C00G C00A C00E 109.3(2) . . ?
C00A C00B H00B 118.2 . . ?
C00H C00B C00A 123.7(2) . . ?
C00H C00B H00B 118.2 . . ?
C007 C00C H00C 119.6 . . ?
C00J C00C C007 120.8(3) . . ?
C00J C00C H00C 119.6 . . ?
N006 C00D C00F 108.6(2) . . ?
C009 C00D N006 110.2(2) . . ?
C009 C00D C00F 141.0(3) . . ?
O002 C00E N006 126.7(3) . . ?
O002 C00E C00A 127.7(3) . . ?
N006 C00E C00A 105.6(2) . . ?
C00M C00F C00D 111.8(3) . . ?
C00M C00F C00N 118.2(3) . . ?
C00N C00F C00D 129.9(2) . . ?
C00A C00G H00G 118.7 . . ?
C00P C00G C00A 122.7(3) . . ?
C00P C00G H00G 118.7 . . ?
C00B C00H H00H 119.1 . . ?
C00B C00H C00I 121.8(3) . . ?
C00I C00H H00H 119.1 . . ?
O004 C00I C00H 122.1(3) . . ?
O004 C00I C00P 121.3(3) . . ?
C00H C00I C00P 116.7(3) . . ?
C00C C00J H00J 119.8 . . ?
C00L C00J C00C 120.3(3) . . ?
C00L C00J H00J 119.8 . . ?
C008 C00K H00K 119.9 . . ?
C00L C00K C008 120.1(3) . . ?
C00L C00K H00K 119.9 . . ?
C00J C00L C00K 120.0(3) . . ?
C00J C00L H00L 120.0 . . ?
C00K C00L H00L 120.0 . . ?
C00F C00M S001 113.0(2) . . ?
C00F C00M C00Q 122.3(3) . . ?
C00Q C00M S001 124.7(3) . . ?
C00F C00N H00N 120.2 . . ?
C00O C00N C00F 119.6(3) . . ?
C00O C00N H00N 120.2 . . ?
C00N C00O H00O 119.4 . . ?
C00R C00O C00N 121.2(3) . . ?
C00R C00O H00O 119.4 . . ?
C00G C00P C00I 122.2(3) . . ?
C00G C00P H00P 118.9 . . ?
C00I C00P H00P 118.9 . . ?
C00M C00Q H00Q 121.4 . . ?
C00R C00Q C00M 117.1(3) . . ?
C00R C00Q H00Q 121.4 . . ?
C00O C00R C00Q 121.5(3) . . ?
C00O C00R H00R 119.2 . . ?
C00Q C00R H00R 119.2 . . ?
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
S001 O003 1.419(2) . ?
S001 O005 1.423(2) . ?
S001 N006 1.670(2) . ?
S001 C00M 1.748(3) . ?
O002 C00E 1.199(3) . ?
O004 C00I 1.228(3) . ?
N006 C00D 1.426(3) . ?
N006 C00E 1.376(4) . ?
C007 C008 1.392(3) . ?
C007 C009 1.470(3) . ?
C007 C00C 1.395(3) . ?
C008 H008 0.9300 . ?
C008 C00K 1.376(4) . ?
C009 C00A 1.534(4) . ?
C009 C00D 1.345(3) . ?
C00A C00B 1.497(3) . ?
C00A C00E 1.555(4) . ?
C00A C00G 1.491(4) . ?
C00B H00B 0.9300 . ?
C00B C00H 1.314(3) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.374(3) . ?
C00D C00F 1.464(4) . ?
C00F C00M 1.386(4) . ?
C00F C00N 1.390(4) . ?
C00G H00G 0.9300 . ?
C00G C00P 1.328(4) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.450(4) . ?
C00I C00P 1.452(4) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.371(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.372(4) . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.399(4) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.371(4) . ?
C00O H00O 0.9300 . ?
C00O C00R 1.363(4) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.370(5) . ?
C00R 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
S001 N006 C00D C009 178.42(17) . . . . ?
S001 N006 C00D C00F 2.1(3) . . . . ?
S001 N006 C00E O002 3.3(4) . . . . ?
S001 N006 C00E C00A -175.27(18) . . . . ?
S001 C00M C00Q C00R 177.9(2) . . . . ?
O003 S001 N006 C00D 112.3(2) . . . . ?
O003 S001 N006 C00E -71.4(3) . . . . ?
O003 S001 C00M C00F -109.9(2) . . . . ?
O003 S001 C00M C00Q 71.1(3) . . . . ?
O004 C00I C00P C00G 175.5(3) . . . . ?
O005 S001 N006 C00D -116.93(19) . . . . ?
O005 S001 N006 C00E 59.4(3) . . . . ?
O005 S001 C00M C00F 113.4(2) . . . . ?
O005 S001 C00M C00Q -65.5(3) . . . . ?
N006 S001 C00M C00F 1.6(2) . . . . ?
N006 S001 C00M C00Q -177.4(3) . . . . ?
N006 C00D C00F C00M -0.8(3) . . . . ?
N006 C00D C00F C00N 175.3(3) . . . . ?
C007 C008 C00K C00L 1.6(4) . . . . ?
C007 C009 C00A C00B 73.2(3) . . . . ?
C007 C009 C00A C00E -174.0(2) . . . . ?
C007 C009 C00A C00G -56.3(3) . . . . ?
C007 C009 C00D N006 174.4(2) . . . . ?
C007 C009 C00D C00F -11.2(5) . . . . ?
C007 C00C C00J C00L -0.5(4) . . . . ?
C008 C007 C009 C00A 141.9(2) . . . . ?
C008 C007 C009 C00D -35.5(4) . . . . ?
C008 C007 C00C C00J 1.8(4) . . . . ?
C008 C00K C00L C00J -0.3(4) . . . . ?
C009 C007 C008 C00K -179.2(2) . . . . ?
C009 C007 C00C C00J 178.7(2) . . . . ?
C009 C00A C00B C00H -135.1(3) . . . . ?
C009 C00A C00E O002 178.6(3) . . . . ?
C009 C00A C00E N006 -2.9(2) . . . . ?
C009 C00A C00G C00P 133.7(3) . . . . ?
C009 C00D C00F C00M -175.3(3) . . . . ?
C009 C00D C00F C00N 0.8(5) . . . . ?
C00A C009 C00D N006 -3.3(3) . . . . ?
C00A C009 C00D C00F 171.2(3) . . . . ?
C00A C00B C00H C00I 2.0(4) . . . . ?
C00A C00G C00P C00I 0.4(4) . . . . ?
C00B C00A C00E O002 -63.0(3) . . . . ?
C00B C00A C00E N006 115.5(2) . . . . ?
C00B C00A C00G C00P 4.1(4) . . . . ?
C00B C00H C00I O004 -176.7(3) . . . . ?
C00B C00H C00I C00P 2.8(4) . . . . ?
C00C C007 C008 C00K -2.3(4) . . . . ?
C00C C007 C009 C00A -34.9(3) . . . . ?
C00C C007 C009 C00D 147.7(3) . . . . ?
C00C C00J C00L C00K -0.3(4) . . . . ?
C00D N006 C00E O002 179.7(2) . . . . ?
C00D N006 C00E C00A 1.2(3) . . . . ?
C00D C009 C00A C00B -109.0(2) . . . . ?
C00D C009 C00A C00E 3.8(2) . . . . ?
C00D C009 C00A C00G 121.5(2) . . . . ?
C00D C00F C00M S001 -0.7(3) . . . . ?
C00D C00F C00M C00Q 178.3(2) . . . . ?
C00D C00F C00N C00O -177.3(3) . . . . ?
C00E N006 C00D C009 1.4(3) . . . . ?
C00E N006 C00D C00F -175.0(2) . . . . ?
C00E C00A C00B C00H 113.6(3) . . . . ?
C00E C00A C00G C00P -112.4(3) . . . . ?
C00F C00M C00Q C00R -1.0(5) . . . . ?
C00F C00N C00O C00R 0.3(5) . . . . ?
C00G C00A C00B C00H -5.4(4) . . . . ?
C00G C00A C00E O002 58.2(3) . . . . ?
C00G C00A C00E N006 -123.3(2) . . . . ?
C00H C00I C00P C00G -4.1(4) . . . . ?
C00M S001 N006 C00D -2.1(2) . . . . ?
C00M S001 N006 C00E 174.2(3) . . . . ?
C00M C00F C00N C00O -1.3(4) . . . . ?
C00M C00Q C00R C00O -0.1(5) . . . . ?
C00N C00F C00M S001 -177.34(19) . . . . ?
C00N C00F C00M C00Q 1.7(4) . . . . ?
C00N C00O C00R C00Q 0.5(5) . . . . ?
