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_7160039
_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         'C13 H14 Cl N O'
_chemical_formula_sum            'C13 H14 Cl N O'
_chemical_formula_weight         235.70
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-03
_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                 103.405(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9223(2)
_cell_length_b                   5.97560(10)
_cell_length_c                   18.2274(4)
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9370
_cell_measurement_theta_min      4.3170
_cell_volume                     1157.24(4)
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_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    -74.00  15.00   0.50    0.17    --  -38.50 100.00  14.00  178
  2  \w     35.00 107.00   0.50    1.14    --  102.00-100.00 -90.00  144
  3  \w    104.00 170.00   0.50    1.14    --  102.00 100.00  14.00  132
  4  \w   -101.00 -27.00   0.50    0.17    --  -38.50 -57.00 150.00  148
  5  \w   -108.00 -33.00   0.50    0.17    --  -38.50 -19.00-150.00  150
  6  \w     46.00 115.00   0.50    0.17    --   48.81  38.00  30.00  138
  7  \w     37.00 112.00   0.50    0.17    --   48.81  57.00  30.00  150
  8  \w      7.00  84.00   0.50    0.17    --   48.81-100.00 -90.00  154
  9  \w     98.00 167.00   0.50    1.14    --  102.00  45.00  90.00  138
 10  \w     39.00 115.00   0.50    1.14    --  102.00 -61.00-120.00  152
 11  \w     94.00 171.00   0.50    1.14    --  102.00  15.00  90.00  154
 12  \w     34.00 105.00   0.50    1.14    --  102.00 -30.00 -60.00  142
 13  \w     89.00 165.00   0.50    1.14    --  102.00  61.00 -60.00  152
 14  \w     34.00 110.00   0.50    1.14    --  102.00 -15.00 -90.00  152
 15  \w     34.00 105.00   0.50    1.14    --  102.00 -30.00 120.00  142
 16  \w    103.00 167.00   0.50    1.14    --  102.00  77.00 -90.00  128
 17  \w     97.00 165.00   0.50    1.14    --  102.00 125.00 120.00  136
 18  \w     42.00  99.00   0.50    1.14    --  102.00 -45.00  60.00  114
;
_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      0.0661009000
_diffrn_orient_matrix_UB_12      -0.0274972000
_diffrn_orient_matrix_UB_13      -0.0654654000
_diffrn_orient_matrix_UB_21      0.1233945000
_diffrn_orient_matrix_UB_22      0.0883952000
_diffrn_orient_matrix_UB_23      0.0507644000
_diffrn_orient_matrix_UB_31      0.0377427000
_diffrn_orient_matrix_UB_32      -0.2406773000
_diffrn_orient_matrix_UB_33      0.0261943000
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.374
_diffrn_reflns_theta_min         4.327
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38335
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0565P)^2^+0.4874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2173
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00957f2.cif
_cod_data_source_block           bb-rs-p3-182_auto
_cod_depositor_comments
'Adding full bibliography for 7160038--7160040.cif.'
_cod_database_code               7160039
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.772
_shelx_estimated_absorpt_t_min   0.611
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C5(H5), C4(H4)
;
_shelx_res_checksum              17575
_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 3.248
_oxdiff_exptl_absorpt_empirical_full_min 0.591