Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles.
Qiu, Jiashen; Wu, Di; Yuan, Lexia; Long, Pingliang; Yin, Hongquan; Chen, Fu-Xue; The Journal of organic chemistry 84 (2019) 7917–7926; doi:10.1021/acs.joc.9b00782

data_4034661
_publ_section_title
;
 Organocatalyzed Asymmetric \a-Thiocyanation of Oxindoles: Synthesis of
 Chiral Tertiary 3-Thiocyanatoxindoles.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7917
_journal_page_last               7926
_journal_paper_doi               10.1021/acs.joc.9b00782
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C21 H20 N2 O4 S'
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_cell_length_c                   17.0090(10)
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_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.23
_cell_volume                     2026.3(2)
_computing_cell_refinement       'Bruker SMART'
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_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.998
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.750
_diffrn_reflns_theta_min         1.938
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   none
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_exptl_crystal_description       block
_exptl_crystal_F_000             832
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0617P)^2^+0.5605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2991
_reflns_number_total             3458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00782_si_002.cif
_cod_data_source_block           qjs321
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034661
_shelxl_version_number           2014-3
_shelx_res_checksum              63309
_shelx_hkl_checksum              92006