Iron- and base-catalyzed <i>C</i>(α)-alkylation and one-pot sequential alkylation-hydroxylation of oxindoles with secondary alcohols.
Saha, Ratnakar; Hembram, Bhairab Chand; Panda, Surajit; Jana, Narayan Ch; Bagh, Bidraha; Organic & biomolecular chemistry 22 (2024) 6321–6330; doi:10.1039/d4ob00957f

data_7160038
_publ_section_title
;
 Iron- and base-catalyzed <i>C</i>(&#x3b1;)-alkylation and one-pot
 sequential alkylation-hydroxylation of oxindoles with secondary alcohols.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6321
_journal_page_last               6330
_journal_paper_doi               10.1039/d4ob00957f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C11 H13 N O'
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.340(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.3851(7)
_cell_length_b                   5.29270(10)
_cell_length_c                   18.3278(6)
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    297.46(10)
_cell_measurement_theta_max      75.2290
_cell_measurement_theta_min      4.4010
_cell_volume                     1932.20(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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   -101.00 -28.00   0.50    0.44    --  -38.50 -55.00 -17.00  146
  2  \w    -49.00  25.00   0.50    0.44    --  -38.50  55.00 125.00  148
  3  \w     39.00 112.00   0.50    0.44    --   49.06  55.00 125.00  146
  4  \w    -14.00  60.00   0.50    0.44    --   49.06 -55.00 -17.00  148
  5  \w     92.00 165.00   0.50    1.49    --  102.00  55.00 125.00  146
  6  \w     39.00 113.00   0.50    1.49    --  102.00 -55.00 -17.00  148
  7  \w    -42.00  28.00   0.50    0.44    --  -38.50  38.00 -90.00  140
  8  \w    -50.00  24.00   0.50    0.44    --  -38.50  57.00-180.00  148
  9  \w    103.00 167.00   0.50    1.49    --  102.00  77.00  30.00  128
 10  \w    103.00 167.00   0.50    1.49    --  102.00  77.00  60.00  128
 11  \w     97.00 165.00   0.50    1.49    --  102.00 125.00   0.00  136
 12  \w    103.00 167.00   0.50    1.49    --  102.00  77.00-120.00  128
 13  \w     99.00 170.00   0.50    1.49    --  102.00  30.00  30.00  142
 14  \w     98.00 167.00   0.50    1.49    --  102.00  45.00   0.00  138
 15  \w     38.00 107.00   0.50    1.49    --  102.00 -45.00 120.00  138
 16  \w     97.00 165.00   0.50    1.49    --  102.00 125.00-120.00  136
 17  \w     34.00 105.00   0.50    1.49    --  102.00 -30.00 120.00  142
 18  \w     97.00 165.00   0.50    1.49    --  102.00 125.00 120.00  136
 19  \w     38.00 112.00   0.50    0.44    --   49.06  57.00 -90.00  148
 20  \w     38.00 112.00   0.50    0.44    --   49.06  57.00-150.00  148
 21  \w     38.00 112.00   0.50    0.44    --   49.06  57.00  60.00  148
 22  \w     38.00 112.00   0.50    0.44    --   49.06  57.00-180.00  148
 23  \w     38.00 112.00   0.50    0.44    --   49.06  57.00 -30.00  148
 24  \w     98.00 154.00   0.50    1.49    --  102.00  45.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.471
_diffrn_reflns_theta_min         4.439
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0596P)^2^+0.4735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1660
_reflns_number_total             1973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00957f2.cif
_cod_data_source_block           bb-rs-isopropanol_oxin_auto
_cod_depositor_comments
'Adding full bibliography for 7160038--7160040.cif.'
_cod_database_code               7160038
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              86322
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;