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_7160040
_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         '2(C16 H15 N O2)'
_chemical_formula_sum            'C32 H30 N2 O4'
_chemical_formula_weight         506.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-01
_audit_creation_method
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_audit_update_record
;
2024-05-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.182(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2634(2)
_cell_length_b                   24.2647(7)
_cell_length_c                   14.6681(4)
_cell_measurement_reflns_used    6931
_cell_measurement_temperature    100.04(10)
_cell_measurement_theta_max      77.9360
_cell_measurement_theta_min      6.0460
_cell_volume                     2574.60(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.04(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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    -75.00  13.00   0.50    0.20    --  -38.50 103.00  10.00  176
  2  \w      8.00  87.00   0.50    0.20    --   49.56-103.00 -92.00  158
  3  \w    104.00 175.00   0.50    0.92    --  107.46 103.00  10.00  142
  4  \w     40.00 108.00   0.50    0.92    --  107.46-103.00 -92.00  136
  5  \w    -42.00  28.00   0.50    0.20    --  -38.50  37.00-180.00  140
  6  \w    -44.00  31.00   0.50    0.20    --  -38.50  19.00 150.00  150
  7  \w    -42.00  28.00   0.50    0.20    --  -38.50  37.00 -30.00  140
  8  \w    -17.00  53.00   0.50    0.20    --   49.56 -37.00-180.00  140
  9  \w     43.00 112.00   0.50    0.92    --  107.46 -45.00  90.00  138
 10  \w     39.00 107.00   0.50    0.92    --  107.46 -94.00 -60.00  136
 11  \w     45.00 121.00   0.50    0.92    --  107.46 -61.00 -90.00  152
 12  \w     39.00 111.00   0.50    0.92    --  107.46 -30.00-180.00  144
 13  \w    103.00 172.00   0.50    0.92    --  107.46  77.00-180.00  138
 14  \w     45.00 113.00   0.50    0.92    --  107.46-125.00  90.00  136
 15  \w     43.00 112.00   0.50    0.92    --  107.46 -45.00  30.00  138
 16  \w     39.00  98.00   0.50    0.92    --  107.46 -94.00-180.00  118
 17  \w     42.00 104.00   0.50    0.92    --  107.46 -30.00  90.00  124
 18  \w     45.00 120.00   0.50    0.92    --  107.46 -61.00  30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513273000
_diffrn_orient_matrix_UB_12      -0.0459923000
_diffrn_orient_matrix_UB_13      0.0656080000
_diffrn_orient_matrix_UB_21      0.0304219000
_diffrn_orient_matrix_UB_22      0.0400903000
_diffrn_orient_matrix_UB_23      0.0813146000
_diffrn_orient_matrix_UB_31      -0.2044894000
_diffrn_orient_matrix_UB_32      0.0175220000
_diffrn_orient_matrix_UB_33      -0.0142989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10691
_diffrn_reflns_point_group_measured_fraction_full 0.632
_diffrn_reflns_point_group_measured_fraction_max 0.607
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.258
_diffrn_reflns_theta_min         3.532
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78355
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0626P)^2^+0.2116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.237
_reflns_Friedel_fraction_full    0.262
_reflns_Friedel_fraction_max     0.233
_reflns_number_gt                3043
_reflns_number_total             3351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00957f2.cif
_cod_data_source_block           bb-rs_p3
_cod_depositor_comments
'Adding full bibliography for 7160038--7160040.cif.'
_cod_database_code               7160040
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.874
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9B(H9B), C9A(H9A)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1B(H1B), C6B(H6B), C12B(H12B), C7B(H7B), C16A(H16A), C6A(H6A),
 C14B(H14B), C15A(H15A), C4B(H4B), C5B(H5B), C7A(H7A), C4A(H4A), C16B(H16B),
 C5A(H5A), C12A(H12A), C13B(H13B), C15B(H15B), C14A(H14A), C13A(H13A)
2.c Idealised Me refined as rotating group:
 C10A(H10D,H10E,H10F), C10B(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2B(H2B), O2A(H2A)
;
_shelx_res_checksum              51401
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.714