Phosphine-catalyzed enantioselective and diastereodivergent [3+2] cyclization for the construction of oxetane dispirooxindole skeletons.
Han, Xiao; Hou, Jie; Zhang, Haiyan; Wang, Zhen; Yao, Weijun; Chemical communications (Cambridge, England) 60 (2024) 10736–10739; doi:10.1039/d4cc03610g

data_7133664
_publ_section_title
;
 Phosphine-catalyzed enantioselective and diastereodivergent [3+2]
 cyclization for the construction of oxetane dispirooxindole skeletons.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10736
_journal_page_last               10739
_journal_paper_doi               10.1039/d4cc03610g
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H22 Br N O5'
_chemical_formula_sum            'C25 H22 Br N O5'
_chemical_formula_weight         496.34
_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_date             2022-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2024-06-10 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.036(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.958(4)
_cell_length_b                   13.864(6)
_cell_length_c                   9.026(4)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.28
_cell_volume                     1120.3(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0435
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4355
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.694
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                2475
_reflns_number_total             3275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03610g2.cif
_cod_data_source_block           y
_cod_depositor_comments
'Adding full bibliography for 7133664--7133666.cif.'
_cod_database_code               7133664
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.214) H1B(0.214) H1C(0.214) H2A(0.135) H2B(0.135) H7(0.055)
 H8(0.064) H9A(0.073) H9B(0.073) H10A(0.081) H10B(0.081) H12(0.067) H13(0.082)
 H14(0.081) H15(0.079) H16(0.07) H20(0.052) H22(0.064) H23(0.065) H25A(0.143)
 H25B(0.143) H25C(0.143)
 Fixed X: H1A(0.709992) H1B(0.853079) H1C(0.697089) H2A(0.830708)
 H2B(0.846479) H7(0.171366) H8(0.352121) H9A(0.665428) H9B(0.541842)
 H10A(0.362465) H10B(0.495388) H12(0.23283) H13(0.057447) H14(-0.176207) H15(-
 0.231066) H16(-0.061531) H20(0.470086) H22(0.355423) H23(0.208612)
 H25A(0.051268) H25B(-0.068283) H25C(-0.072387)
 Fixed Y: H1A(0.544208) H1B(0.48076) H1C(0.43144) H2A(0.423792) H2B(0.53656)
 H7(0.601803) H8(0.482471) H9A(0.621946) H9B(0.632478) H10A(0.772768)
 H10B(0.755066) H12(0.354113) H13(0.236715) H14(0.280576) H15(0.439212)
 H16(0.557938) H20(0.410665) H22(0.332576) H23(0.471843) H25A(0.791747)
 H25B(0.720725) H25C(0.748473)
 Fixed Z: H1A(0.952581) H1B(0.980598) H1C(0.952961) H2A(0.752465)
 H2B(0.752616) H7(0.508812) H8(0.643477) H9A(0.30477) H9B(0.174177)
 H10A(0.394613) H10B(0.51387) H12(0.498565) H13(0.436347) H14(0.353185)
 H15(0.314155) H16(0.372056) H20(0.319706) H22(-0.098224) H23(-0.127392)
 H25A(0.023506) H25B(0.084142) H25C(-0.084322)
;
_shelx_res_checksum              50549
_shelx_hkl_checksum              76392
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'