Asymmetric catalytic synthesis of spirocyclobutyl oxindoles and beyond via [2+2] cycloaddition and sequential transformations
Zhong, Xia; Tan, Jiuqi; Qiao, Jianglin; Zhou, Yuqiao; Lv, Cidan; Su, Zhishan; Dong, Shunxi; Feng, Xiaoming; Chemical Science  (2021) –; doi:10.1039/D1SC02681J

data_1563782
_publ_section_title
;
 Asymmetric catalytic synthesis of spirocyclobutyl oxindoles and beyond
 via [2+2] cycloaddition and sequential transformations
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02681J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H38 N2 O7 S'
_chemical_formula_sum            'C35 H38 N2 O7 S'
_chemical_formula_weight         630.73
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-06 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6132(4)
_cell_length_b                   17.1589(7)
_cell_length_c                   20.1048(9)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      80.25
_cell_measurement_theta_min      3.39
_cell_volume                     3316.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      148(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            86721
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.721
_diffrn_reflns_theta_min         3.386
_exptl_absorpt_coefficient_mu    1.280
_exptl_absorpt_correction_T_max  0.8946
_exptl_absorpt_correction_T_min  0.7363
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, Hexane'
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 3060 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.014(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         7224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0372P)^2^+0.5823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                7063
_reflns_number_total             7224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02681j2.cif
_cod_data_source_block           zhx024
_cod_database_code               1563782
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.702
_shelx_estimated_absorpt_t_max   0.850
_shelx_res_checksum              23393
_shelx_hkl_checksum              10436