Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates.
Gui, Hou-Ze; Wei, Yin; Shi, Min; Organic & biomolecular chemistry 16 (2018) 9218–9222; doi:10.1039/c8ob02748j

data_7156577
_publ_section_title
;
 Construction of spirothioureas having an amino quaternary stereogenic
 center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with
 2-aminoacrylates.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9218
_journal_page_last               9222
_journal_paper_doi               10.1039/c8ob02748j
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C29 H28 Br N3 O6 S2'
_chemical_formula_weight         658.57
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-09-14 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.849(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6362(13)
_cell_length_b                   13.2220(16)
_cell_length_c                   11.2568(14)
_cell_measurement_reflns_used    3365
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      46.201
_cell_measurement_theta_min      4.671
_cell_volume                     1522.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11125
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.990
_exptl_absorpt_coefficient_mu    1.532
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
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_refine_diff_density_max         0.854
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.554(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5973
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.9961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4575
_reflns_number_total             5973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02748j3.cif
_cod_data_source_block           mo_dm18055_0m
_cod_depositor_comments
'Adding full bibliography for 7156576--7156577.cif.'
_cod_database_code               7156577
_shelx_estimated_absorpt_t_min   0.770
_shelx_estimated_absorpt_t_max   0.837
_shelxl_version_number           2013-4
_shelx_res_checksum              64031
_shelx_hkl_checksum              14345