Asymmetric synthesis of spirooxindole-fused spirothiazolones via squaramide-catalysed reaction of 3-chlorooxindoles with 5-alkenyl thiazolones.
Song, Yong-Xing; Du, Da-Ming; Organic & biomolecular chemistry 17 (2019) 5375–5380; doi:10.1039/c9ob00998a

data_7156860
_publ_section_title
;
 Asymmetric synthesis of spirooxindole-fused spirothiazolones via
 squaramide-catalysed reaction of 3-chlorooxindoles with 5-alkenyl
 thiazolones.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5375
_journal_page_last               5380
_journal_paper_doi               10.1039/c9ob00998a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H15 Br N2 O2 S'
_chemical_formula_sum            'C24 H15 Br N2 O2 S'
_chemical_formula_weight         475.35
_chemical_melting_point          453.0(10)
_chemical_name_systematic
(2'S,3R,3'S)-3'-(4-bromophenyl)-2''-phenyl-4''H-dispiro[indoline-3,1'-cyclopropane-2',5''-thiazole]-2,4''-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-25 deposited with the CCDC.    2019-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                74.87(3)
_cell_angle_beta                 89.66(3)
_cell_angle_gamma                71.84(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8036(18)
_cell_length_b                   10.750(2)
_cell_length_c                   11.597(2)
_cell_measurement_reflns_used    3275
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.8253
_cell_volume                     1003.3(4)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9228
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.359
_exptl_absorpt_coefficient_mu    2.177
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether-ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0386
_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/[\s^2^(Fo^2^)+(0.0421P)^2^+0.9036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4254
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00998a2.cif
_cod_data_source_block           bwn19069
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '452-454' was changed to '453.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156860.cif.
;
_cod_database_code               7156860
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.670
_shelx_estimated_absorpt_t_min   0.612
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'