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_7240270
_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_sum            'C26 H24 Cl F N2 O3'
_chemical_formula_weight         466.92
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_volume                     2496.91(14)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
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_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
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_diffrn_measured_fraction_theta_max 0.978
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_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
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_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
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_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_min         4.593
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
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_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
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_exptl_crystal_description       block
_exptl_crystal_F_000             976
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_exptl_crystal_size_min          .14
_refine_diff_density_max         0.244
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_refine_ls_extinction_coef       0.0039(4)
_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   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0920P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3419
_reflns_number_total             4839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02374d2.cif
_cod_data_source_block           FVE761
_cod_depositor_comments
'Adding full bibliography for 7240267--7240271.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240270
_shelxl_version_number           2013-4
_shelx_res_checksum              11873