Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles
Zhong, Ziwei; Xiao, Zhijie; Liu, Xiaohua; Cao, Weidi; Feng, Xiaoming; Chemical Science  (2020) –; doi:10.1039/D0SC03776A

data_1559216
_publ_section_title
;
 Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via
 conjugate addition/Schmidt-type rearrangement of vinyl azides and
 (E)-alkenyloxindoles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03776A
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H30 N2 O5'
_chemical_formula_weight         510.57
_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-2016/6
_audit_update_record
;
2020-01-13 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5509(13)
_cell_length_b                   15.2802(19)
_cell_length_c                   16.524(2)
_cell_measurement_reflns_used    9027
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.26
_cell_measurement_theta_min      2.89
_cell_volume                     2664.0(6)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19057
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.255
_diffrn_reflns_theta_min         3.940
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2018)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.2472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4990
_reflns_number_total             5043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03776a2.cif
_cod_data_source_block           cu_20191124ZZW_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1559216
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.743
_shelx_estimated_absorpt_t_max   0.812
_shelx_res_checksum              44752