Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones via the Staudinger reaction: cis- or trans-diastereoselectivity with different addition modes
Filatov, Vadim; Kukushkin, Maksim; Kuznetsova, Juliana; Skvortsov, Dmitry; Tafeenko, Viktor; Zyk, Nikolay; Majouga, Alexander; Beloglazkina, Elena; RSC Advances 10 (2020) 14122–14133; doi:10.1039/D0RA02374D

data_7240267
_publ_section_title
;
 Synthesis of
 1,3-diaryl-spiro[azetidine-2,3&#x2032;-indoline]-2&#x2032;,4-diones via
 the Staudinger reaction: cis- or trans-diastereoselectivity with
 different addition modes
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              14122
_journal_page_last               14133
_journal_paper_doi               10.1039/D0RA02374D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H15 Cl N2 O3,C4 H10 O'
_chemical_formula_sum            'C26 H25 Cl N2 O4'
_chemical_formula_weight         464.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.928(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8999(3)
_cell_length_b                   15.9931(4)
_cell_length_c                   15.6852(5)
_cell_measurement_reflns_used    10568
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.22
_cell_measurement_theta_min      4.01
_cell_volume                     2399.62(13)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16528
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.107
_diffrn_reflns_theta_min         4.019
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.693
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             976
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .13
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0816P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2606
_reflns_number_total             4172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02374d2.cif
_cod_data_source_block           FVE671
_cod_depositor_comments
'Adding full bibliography for 7240267--7240271.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240267
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              28192