Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through cyclopropanation of aza-aurones with tosylhydrazones.
Pirovano, Valentina; Brambilla, Elisa; Riva, Marika; Leoni, Sara; Rizzato, Silvia; Garanzini, Davide; Abbiati, Giorgio; Rossi, Elisabetta; Organic & biomolecular chemistry 19 (2021) 3925–3931; doi:10.1039/d1ob00076d

data_7158010
_publ_section_title
;
 Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through
 cyclopropanation of aza-aurones with tosylhydrazones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3925
_journal_page_last               3931
_journal_paper_doi               10.1039/d1ob00076d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2021-01-12 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.272(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.301(2)
_cell_length_b                   6.870(1)
_cell_length_c                   29.971(6)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.3
_cell_measurement_wavelength     0.71073
_cell_volume                     2103.9(7)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
'SIR 2014: C. Giacovazzo et all., J. Appl. Cryst.(2015) 48, 306'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD_plate
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker apex II ccd diffractometer'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12735
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        22.70
_diffrn_reflns_theta_max         22.70
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+1.2343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0
_reflns_number_gt                2001
_reflns_number_total             2824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00076d2.cif
_cod_data_source_block           3n
_cod_depositor_comments          'Adding full bibliography for 7158010.cif.'
_cod_original_cell_volume        2103.8(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158010