Alkene carboamination/oxidative denitrogenation of 3-allyl-3-hydrazinylindolin-2-ones: one-pot entry to spirocyclopropyloxindoles.
Manenti, Marco; Villa, Tommaso; Macetti, Giovanni; Silvani, Alessandra; Organic & biomolecular chemistry 22 (2024) 2124–2136; doi:10.1039/d3ob02115g

data_7159809
_publ_section_title
;
 Alkene carboamination/oxidative denitrogenation of
 3-allyl-3-hydrazinylindolin-2-ones: one-pot entry to
 spirocyclopropyloxindoles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2124
_journal_page_last               2136
_journal_paper_doi               10.1039/d3ob02115g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C51 H28 Br N O2'
_chemical_formula_sum            'C51 H38 Br N O2'
_chemical_formula_weight         776.73
_chemical_melting_point          526.0(10)
_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   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-10-20
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.859(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2019(13)
_cell_length_b                   9.5258(5)
_cell_length_c                   24.3433(12)
_cell_measurement_reflns_used    4510
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.0650
_cell_measurement_theta_min      3.2170
_cell_volume                     4729.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -55.00 -26.00   0.50   16.77    --   -0.55 -71.00 107.00   58
  2  \w    -21.00  11.00   0.50   16.77    --   -0.55  71.00-122.00   64
  3  \w     35.00 128.00   0.50   45.00    --   55.05  71.00-122.00  186
  4  \w     -5.00  75.00   0.50   45.00    --   55.05 -71.00 107.00  160
  5  \w   -114.00 -67.00   0.50   45.00    --  -56.15 -71.00 107.00   94
  6  \w    -70.00 -43.00   0.50   45.00    --  -56.15  71.00-122.00   54
  7  \w     75.00 101.00   0.50   45.00    --   55.05-125.00-180.00   52
  8  \w    -20.00   5.00   0.50   45.00    --   55.05 -19.00  90.00   50
  9  \w    -12.00  15.00   0.50   45.00    --   55.05 -19.00 150.00   54
 10  \w    -14.00  23.00   0.50   45.00    --   55.05 -19.00 -90.00   74
 11  \w    -20.00  24.00   0.50   45.00    --   55.05 -19.00 120.00   88
 12  \w   -126.00 -88.00   0.50   45.00    --  -56.15-125.00 -90.00   76
 13  \w    -39.00   7.00   0.50   45.00    --  -56.15  38.00-150.00   92
 14  \w    -24.00  16.00   0.50   45.00    --  -56.15  19.00  60.00   80
 15  \w    -44.00   8.00   0.50   45.00    --  -56.15  38.00   0.00  104
 16  \w   -126.00 -55.00   0.50   45.00    --  -56.15 -19.00   0.00  142
 17  \w    -66.00 -41.00   0.50   45.00    --  -56.15 -57.00  30.00   50
 18  \w   -127.00 -63.00   0.50   45.00    --  -56.15 -19.00 150.00  128
 19  \w   -102.00 -77.00   0.50   45.00    --  -56.15 -57.00  30.00   50
 20  \w   -124.00 -58.00   0.50   45.00    --  -56.15 -38.00 -30.00  132
 21  \w   -120.00 -73.00   0.50   45.00    --  -56.15-125.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2132
_diffrn_reflns_av_unetI/netI     0.1430
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26125
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        51.825
_diffrn_reflns_theta_max         51.825
_diffrn_reflns_theta_min         3.239
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent pale colorles'
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       needle
_exptl_crystal_F_000             1608
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1013P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             5126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02115g2.cif
_cod_data_source_block           mm103
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '525-527 K' was changed to
'526.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159808--7159809.cif.
;
_cod_original_cell_volume        4729.3(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159809
_shelx_res_checksum              32524
_shelx_fab_checksum              8166