Stereoselective sulfenylation of oxindole-derived propargyl alcohols to access sulfenylated-3-alkenyloxindoles.
Khan, Tabassum; Rajesh, Pallava; Arun, Doma; Yaragorla, Srinivasarao; Organic & biomolecular chemistry 19 (2021) 10201–10209; doi:10.1039/d1ob01921j

data_7158399
_publ_section_title
;
 Stereoselective sulfenylation of oxindole-derived propargyl alcohols to
 access sulfenylated-3-alkenyloxindoles.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10201
_journal_page_last               10209
_journal_paper_doi               10.1039/d1ob01921j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C22 H17 N O S'
_chemical_formula_sum            'C22 H17 N O S'
_chemical_formula_weight         343.42
_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
_audit_creation_date             2021-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                115.159(12)
_cell_angle_beta                 102.060(13)
_cell_angle_gamma                95.668(13)
_cell_formula_units_Z            2
_cell_length_a                   7.472(2)
_cell_length_b                   10.980(3)
_cell_length_c                   12.170(4)
_cell_measurement_reflns_used    3248
_cell_measurement_temperature    298.22
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.85
_cell_volume                     863.7(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2059
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.750
_diffrn_reflns_theta_min         2.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0779
_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/[\s^2^(Fo^2^)+(0.0309P)^2^+0.7274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1946
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01921j2.cif
_cod_data_source_block           ysr32a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7158399.cif.'
_cod_database_code               7158399
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C16(H16), C2(H2), C14(H14), C15(H15), C18(H18), C3(H3),
 C22(H22), C6(H6), C4(H4), C19(H19), C20(H20), C21(H21), C5(H5)
;
_shelx_res_checksum              43649
_olex2_submission_original_sample_id SYTK-SPh-1
_olex2_submission_special_instructions 'No special instructions were received'