#------------------------------------------------------------------------------
#$Date: 2024-05-05 03:57:43 +0300 (Sun, 05 May 2024) $
#$Revision: 291524 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132885.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_7132885
loop_
_publ_author_name
'Li, Hongye'
'Zhou, Yuqiao'
'Tan, Zheng'
'Wang, Xiangyu'
'Zhang, Yuxin'
'Wang, Fei'
'Feng, Xiaoming'
'Liu, Xiaohua'
_publ_section_title
;
 Enantioselective sulfonylation to construct 3-sulfonylated oxindoles.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4354
_journal_page_last               4357
_journal_paper_doi               10.1039/d4cc00802b
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N O3 S'
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-07-26 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.0000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5669(3)
_cell_length_b                   8.0829(2)
_cell_length_c                   11.7127(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.10
_cell_volume                     920.87(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14671
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         4.100
_exptl_absorpt_coefficient_mu    1.728
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3, PE'
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0298P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3233
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00802b2.cif
_cod_data_source_block           lzj037
_cod_depositor_comments          'Adding full bibliography for 7132885.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132885
_shelx_shelxl_version_number     2019/1
_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   0.577
_shelx_estimated_absorpt_t_max   0.886
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
S S 0.68029(4) 0.63723(6) 0.76519(4) 0.01714(12) Uani 1 1 d . . . . .
O1 O 0.46093(15) 0.6377(3) 0.47498(13) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.72637(16) 0.7299(2) 0.68291(15) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.72069(16) 0.6969(2) 0.89023(15) 0.0262(4) Uani 1 1 d . . . . .
N N 0.37778(19) 0.4263(2) 0.55746(17) 0.0215(4) Uani 1 1 d D . . . .
H1N H 0.354(3) 0.360(4) 0.493(2) 0.038(8) Uiso 1 1 d D . . . .
C1 C 0.4430(2) 0.5712(3) 0.5609(2) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.49124(17) 0.6382(3) 0.69538(16) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.4349(2) 0.5130(3) 0.75727(19) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.4358(2) 0.5072(3) 0.87560(19) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.478066 0.592778 0.933646 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3736(2) 0.3738(3) 0.9079(2) 0.0256(5) Uani 1 1 d . . . . .
H5 H 0.372298 0.368220 0.988503 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3133(2) 0.2488(3) 0.8228(2) 0.0286(5) Uani 1 1 d . . . . .
H6 H 0.273336 0.157170 0.847155 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3096(2) 0.2536(3) 0.7024(2) 0.0270(5) Uani 1 1 d . . . . .
H7 H 0.267156 0.168386 0.644150 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3708(2) 0.3885(3) 0.67198(19) 0.0192(4) Uani 1 1 d . . . . .
C11 C 0.7369(2) 0.4246(3) 0.7704(2) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.676993 0.367962 0.691937 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8848(2) 0.4274(3) 0.7771(2) 0.0273(5) Uani 1 1 d . . . . .
H12A H 0.887294 0.484743 0.703337 0.033 Uiso 1 1 calc R U . . .
H12B H 0.944353 0.489123 0.851851 0.033 Uiso 1 1 calc R U . . .
C13 C 0.9385(3) 0.2512(4) 0.7825(3) 0.0424(7) Uani 1 1 d . . . . .
H13A H 0.883306 0.193078 0.704383 0.051 Uiso 1 1 calc R U . . .
H13B H 1.034952 0.254823 0.789630 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9316(3) 0.1550(4) 0.8916(2) 0.0419(7) Uani 1 1 d . . . . .
H14A H 0.963117 0.040043 0.889866 0.050 Uiso 1 1 calc R U . . .
H14B H 0.993378 0.206786 0.970260 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7861(3) 0.1535(4) 0.8856(3) 0.0390(6) Uani 1 1 d . . . . .
H15A H 0.784241 0.095532 0.959383 0.047 Uiso 1 1 calc R U . . .
H15B H 0.726485 0.091636 0.811016 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7298(3) 0.3288(3) 0.8807(3) 0.0320(5) Uani 1 1 d . . . . .
H16A H 0.784021 0.387611 0.958745 0.038 Uiso 1 1 calc R U . . .
H16B H 0.633190 0.323264 0.872998 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4452(2) 0.8193(3) 0.7010(2) 0.0195(4) Uani 1 1 d . . . . .
H21A H 0.495831 0.864468 0.785204 0.023 Uiso 1 1 calc R U . . .
H21B H 0.467635 0.887988 0.641452 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2926(2) 0.8277(3) 0.6701(2) 0.0202(4) Uani 1 1 d . . . . .
C23 C 0.2413(3) 0.8236(3) 0.7633(2) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.303230 0.816779 0.847666 0.033 Uiso 1 1 calc R U . . .
C24 C 0.1007(3) 0.8292(4) 0.7340(3) 0.0370(6) Uani 1 1 d . . . . .
H24 H 0.067103 0.825272 0.798290 0.044 Uiso 1 1 calc R U . . .
C25 C 0.0099(3) 0.8405(4) 0.6122(3) 0.0445(7) Uani 1 1 d . . . . .
H25 H -0.086324 0.843979 0.592112 0.053 Uiso 1 1 calc R U . . .
C26 C 0.0597(3) 0.8467(5) 0.5192(3) 0.0458(7) Uani 1 1 d . . . . .
H26 H -0.002515 0.855823 0.435048 0.055 Uiso 1 1 calc R U . . .
C27 C 0.1994(2) 0.8397(4) 0.5482(2) 0.0306(5) Uani 1 1 d . . . . .
H27 H 0.232230 0.843182 0.483429 0.037 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O3 S O2 117.45(10) . . ?
O3 S C11 108.73(10) . . ?
O2 S C11 108.69(10) . . ?
O3 S C2 106.84(9) . . ?
O2 S C2 106.93(9) . . ?
C11 S C2 107.82(11) . . ?
C1 N C8 112.10(18) . . ?
O1 C1 N 126.8(2) . . ?
O1 C1 C2 126.1(2) . . ?
N C1 C2 107.09(18) . . ?
C3 C2 C1 102.74(18) . . ?
C3 C2 C21 115.25(16) . . ?
C1 C2 C21 112.84(17) . . ?
C3 C2 S 110.49(14) . . ?
C1 C2 S 108.59(12) . . ?
C21 C2 S 106.83(15) . . ?
C4 C3 C8 120.4(2) . . ?
C4 C3 C2 131.3(2) . . ?
C8 C3 C2 108.36(18) . . ?
C3 C4 C5 118.7(2) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C7 122.0(2) . . ?
C8 C7 C6 116.8(2) . . ?
C7 C8 C3 122.0(2) . . ?
C7 C8 N 128.4(2) . . ?
C3 C8 N 109.61(19) . . ?
C12 C11 C16 110.40(18) . . ?
C12 C11 S 107.69(16) . . ?
C16 C11 S 112.50(16) . . ?
C13 C12 C11 110.1(2) . . ?
C14 C13 C12 111.9(2) . . ?
C15 C14 C13 110.3(2) . . ?
C14 C15 C16 111.6(3) . . ?
C15 C16 C11 110.7(2) . . ?
C22 C21 C2 110.83(17) . . ?
C27 C22 C23 118.1(2) . . ?
C27 C22 C21 120.9(2) . . ?
C23 C22 C21 121.1(2) . . ?
C24 C23 C22 120.7(2) . . ?
C25 C24 C23 120.2(2) . . ?
C24 C25 C26 119.5(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C22 121.2(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
S O3 1.4392(16) . ?
S O2 1.4470(16) . ?
S C11 1.813(2) . ?
S C2 1.8393(17) . ?
O1 C1 1.219(3) . ?
N C1 1.352(3) . ?
N C8 1.405(3) . ?
C1 C2 1.552(3) . ?
C2 C3 1.498(3) . ?
C2 C21 1.552(3) . ?
C3 C4 1.383(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.396(3) . ?
C7 C8 1.383(3) . ?
C11 C12 1.533(3) . ?
C11 C16 1.534(3) . ?
C12 C13 1.526(4) . ?
C13 C14 1.522(4) . ?
C14 C15 1.511(4) . ?
C15 C16 1.529(4) . ?
C21 C22 1.510(3) . ?
C22 C27 1.385(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.389(4) . ?
C24 C25 1.377(4) . ?
C25 C26 1.383(4) . ?
C26 C27 1.381(4) . ?
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
C8 N C1 O1 -177.8(2) . . . . ?
C8 N C1 C2 2.2(2) . . . . ?
O1 C1 C2 C3 176.9(2) . . . . ?
N C1 C2 C3 -3.1(2) . . . . ?
O1 C1 C2 C21 52.2(3) . . . . ?
N C1 C2 C21 -127.79(18) . . . . ?
O1 C1 C2 S -66.0(3) . . . . ?
N C1 C2 S 113.98(16) . . . . ?
O3 S C2 C3 -66.93(17) . . . . ?
O2 S C2 C3 166.51(15) . . . . ?
C11 S C2 C3 49.78(17) . . . . ?
O3 S C2 C1 -178.89(16) . . . . ?
O2 S C2 C1 54.55(18) . . . . ?
C11 S C2 C1 -62.17(17) . . . . ?
O3 S C2 C21 59.13(15) . . . . ?
O2 S C2 C21 -67.42(15) . . . . ?
C11 S C2 C21 175.85(13) . . . . ?
C1 C2 C3 C4 -175.8(2) . . . . ?
C21 C2 C3 C4 -52.6(3) . . . . ?
S C2 C3 C4 68.6(3) . . . . ?
C1 C2 C3 C8 2.9(2) . . . . ?
C21 C2 C3 C8 126.00(19) . . . . ?
S C2 C3 C8 -112.80(16) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C5 179.52(19) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C6 C7 C8 N -177.8(2) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
C2 C3 C8 C7 179.39(19) . . . . ?
C4 C3 C8 N 177.04(19) . . . . ?
C2 C3 C8 N -1.8(2) . . . . ?
C1 N C8 C7 178.4(2) . . . . ?
C1 N C8 C3 -0.3(2) . . . . ?
O3 S C11 C12 -87.06(15) . . . . ?
O2 S C11 C12 41.87(16) . . . . ?
C2 S C11 C12 157.45(13) . . . . ?
O3 S C11 C16 34.81(19) . . . . ?
O2 S C11 C16 163.75(16) . . . . ?
C2 S C11 C16 -80.67(17) . . . . ?
C16 C11 C12 C13 56.5(3) . . . . ?
S C11 C12 C13 179.68(17) . . . . ?
C11 C12 C13 C14 -57.1(3) . . . . ?
C12 C13 C14 C15 56.7(4) . . . . ?
C13 C14 C15 C16 -56.1(3) . . . . ?
C14 C15 C16 C11 56.6(3) . . . . ?
C12 C11 C16 C15 -56.4(3) . . . . ?
S C11 C16 C15 -176.76(17) . . . . ?
C3 C2 C21 C22 -45.3(2) . . . . ?
C1 C2 C21 C22 72.3(2) . . . . ?
S C2 C21 C22 -168.47(14) . . . . ?
C2 C21 C22 C27 -86.3(3) . . . . ?
C2 C21 C22 C23 93.6(2) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C21 C22 C23 C24 -179.2(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
C23 C22 C27 C26 -0.3(4) . . . . ?
C21 C22 C27 C26 179.7(3) . . . . ?
