Enantioselective synthesis of isoxazole-containing spirooxindole tetrahydroquinolines <i>via</i> squaramide-catalysed cascade reactions.
Li, Tong-Hao; Niu, Cheng; Du, Da-Ming; Organic & biomolecular chemistry 20 (2022) 5582–5588; doi:10.1039/d2ob00864e

data_7158760
_publ_section_title
;
 Enantioselective synthesis of isoxazole-containing spirooxindole
 tetrahydroquinolines <i>via</i> squaramide-catalysed cascade reactions.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5582
_journal_page_last               5588
_journal_paper_doi               10.1039/d2ob00864e
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C38 H39 Cl N4 O10 S'
_chemical_formula_weight         779.24
_chemical_melting_point          440.0(10)
_chemical_name_systematic
'(2'R,3S,4'S)-di-tert-butyl 6-chloro-4'-((3-methyl-4-nitroisoxazol-5-yl)methyl)-2-oxo-1'-tosyl-2',4'-dihydro-1'H-spiro[indoline-3,3'-quinoline]-1,2'-dicarboxylate'
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-01 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2003(6)
_cell_length_b                   9.9350(5)
_cell_length_c                   19.3125(10)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.31
_cell_volume                     1942.12(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29644
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.057
_diffrn_reflns_theta_max         25.057
_diffrn_reflns_theta_min         2.012
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: petroleum ether/ethyl acetate'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         6635
_refine_ls_number_restraints     101
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0758
_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^)+(0.1421P)^2^+1.8513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                5162
_reflns_number_total             6635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00864e2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '439-441' was changed to
'440.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158760.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158760
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.959
_shelx_res_checksum              47350