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_7159808
_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         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39
_chemical_melting_point          441.0(10)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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             2023-07-20
_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                84.966(6)
_cell_angle_beta                 76.217(5)
_cell_angle_gamma                62.126(6)
_cell_formula_units_Z            4
_cell_length_a                   11.5430(6)
_cell_length_b                   11.9861(9)
_cell_length_c                   13.8670(9)
_cell_measurement_reflns_used    8484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0060
_cell_measurement_theta_min      2.7750
_cell_volume                     1646.5(2)
_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_molecular_graphics    'Mercury 4.0 (Macrae, 2020)'
_computing_structure_refinement  'SHELXL-2014/4 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.798
_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    -20.00  31.00   0.50   60.00    --   -0.21-100.00  98.00  102
  2  \w    -21.00  29.00   0.50   60.00    --   -0.21 -99.00  30.00  100
  3  \w    -20.00  54.00   0.50   60.00    --   -0.21  77.00-120.00  148
  4  \w    -22.00  30.00   0.50   60.00    --   -0.21 -99.00 150.00  104
  5  \w    -23.00  30.00   0.50   60.00    --   -0.21 -99.00 -90.00  106
  6  \w    -19.00  72.00   0.50   60.00    --   -0.21  77.00-180.00  182
  7  \w    -25.00  12.00   0.50   60.00    --    4.00 -30.00-156.30   74
  8  \w    -60.00  12.00   0.50   60.00    --    4.00 -29.00  46.78  144
  9  \w    -61.00 -29.00   0.50   60.00    --    4.00 -30.00-156.30   64
 10  \w    -11.00  35.00   0.50   60.00    --   -4.00  18.00-106.66   92
 11  \w    -11.00  53.00   0.50   60.00    --   -4.00  15.00 108.95  128
 12  \w    -11.00  68.00   0.50   60.00    --   -4.00  14.00 163.81  158
 13  \w    -12.00   6.50   0.50   60.00    --   -4.00  24.00 -12.78   37
;
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1816
_diffrn_reflns_av_unetI/netI     0.1283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.798
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.303
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent pale colourless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.1597
_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^)+(0.1912P)^2^+10.3480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4266
_refine_ls_wR_factor_ref         0.4461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5996
_reflns_number_total             8604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02115g2.cif
_cod_data_source_block           98freeB
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '440-442' was changed to
'441.0(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.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H38 N2 O2'
_cod_original_formula_weight         650.78
_cod_original_formula_units_Z            2
_cod_database_code               7159808
_shelx_res_checksum              34502