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_4034662
_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            'C20 H17 Cl N2 O3 S'
_chemical_formula_weight         400.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6581(10)
_cell_length_b                   9.9640(12)
_cell_length_c                   23.395(3)
_cell_measurement_reflns_used    6347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.62
_cell_measurement_theta_min      2.51
_cell_volume                     2018.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.951
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19300
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.735
_diffrn_reflns_theta_min         1.741
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
; 
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1116P)^2^+0.2823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1666
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3033
_reflns_number_total             3450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00782_si_003.cif
_cod_data_source_block           qjs111
_cod_original_cell_volume        2018.2(4)
_cod_database_code               4034662
_shelxl_version_number           2014-3
_shelx_res_checksum              22177
_shelx_hkl_checksum              18860