Ligand-Controlled Switch in Diastereoselectivities: Catalytic Asymmetric Construction of Spirocyclic Pyrrolidine-azetidine/oxe(thie)tane Derivatives
Deng, Wei-Ping; Deng, Hua; Jia, Renmeng; Yang, Wu-Lin; Yu, Xingxin; Chemical Communications  (2019) –; doi:10.1039/C9CC03589C

data_7123570
_publ_section_title
;
 Ligand-Controlled Switch in Diastereoselectivities: Catalytic Asymmetric
 Construction of Spirocyclic Pyrrolidine-azetidine/oxe(thie)tane
 Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03589C
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H24 Br N3 O4'
_chemical_formula_weight         450.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2024(3)
_cell_length_b                   31.7463(10)
_cell_length_c                   6.5544(2)
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      49.157
_cell_measurement_theta_min      5.133
_cell_volume                     2122.89(11)
_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 0.986
_diffrn_measured_fraction_theta_max 0.987
_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11503
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.373
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(6)
_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   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.4792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3140
_reflns_number_total             4090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03589c2.cif
_cod_data_source_block           d8v18592
_cod_database_code               7123570
_shelx_estimated_absorpt_t_min   0.695
_shelx_estimated_absorpt_t_max   0.784
_shelxl_version_number           2013-4
_shelx_res_checksum              68776
_shelx_hkl_checksum              58