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_7240268
_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_absolute_configuration ad
_chemical_formula_moiety         'C22 H14 Cl F N2 O2'
_chemical_formula_sum            'C22 H14 Cl F N2 O2'
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_space_group_crystal_system      tetragonal
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_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
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_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
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_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
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_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_point_group_measured_fraction_full 0.984
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_diffrn_source                   'Cu GeniX 3D'
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_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.075
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_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
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_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.027(6)
_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   1.091
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     506
_refine_ls_number_reflns         6307
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_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0685
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1179P)^2^+0.1042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1728
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.831
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                5501
_reflns_number_total             6307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02374d2.cif
_cod_data_source_block           fve762
_cod_depositor_comments
'Adding full bibliography for 7240267--7240271.cif.'
_cod_original_cell_volume        3732.41(14)
_cod_database_code               7240268
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              8240