Direct organocatalytic transfer hydrogenation and C-H oxidation: high-yielding synthesis of 3-hydroxy-3-alkyloxindoles.
Roy, Pritam; Anjum, S. Rehana; Sanwal, Shyam D.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 21 (2023) 8335–8343; doi:10.1039/d3ob01264f

data_7159629
_publ_section_title
;
 Direct organocatalytic transfer hydrogenation and C-H oxidation:
 high-yielding synthesis of 3-hydroxy-3-alkyloxindoles.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8335
_journal_page_last               8343
_journal_paper_doi               10.1039/d3ob01264f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H20 Cl N O4'
_chemical_formula_sum            'C20 H20 Cl N O4'
_chemical_formula_weight         373.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-08-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.455(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.028(5)
_cell_length_b                   24.273(11)
_cell_length_c                   8.467(4)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.625
_cell_measurement_theta_min      2.368
_cell_volume                     1891.0(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297.26
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.168
_diffrn_reflns_av_unetI/netI     0.2241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20330
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4169
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2097
_refine_ls_R_factor_gt           0.0778
_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^)+(0.0310P)^2^+1.3559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2017
_reflns_number_total             4232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01264f3.cif
_cod_data_source_block           dbr75vr_a
_cod_original_cell_volume        1890.9(15)
_cod_database_code               7159629
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C12(H12), C8(H8), C11(H11), C10(H10), C9(H9)
2.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'