Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes
Zhang, Ming-Zhong; Liu, Long; Gou, Quan; Wang, Qi; Li, Yi; Li, Wan-Ting; Luo, Fei; Yuan, Min; Chen, Tieqiao; He, Wei-Min; Green Chemistry 22 (2020) 8369–8374; doi:10.1039/D0GC02205E

data_7241700
_publ_section_title
;
 Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones
 through oxone-mediated cascade arylhydroxylation of activated alkenes
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              8369
_journal_page_last               8374
_journal_paper_doi               10.1039/D0GC02205E
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '2(C16 H14 Cl N O2), 0.5(H4 O2)'
_chemical_formula_sum            'C32 H30 Cl2 N2 O5'
_chemical_formula_weight         593.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-27 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.357(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8614(16)
_cell_length_b                   19.0598(14)
_cell_length_c                   8.8881(6)
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      27.1000
_cell_measurement_theta_min      2.4920
_cell_volume                     2779.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.832
_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    -14.00  29.00   1.00    5.00    --  -11.59 -99.00-180.00   43
  2  \w    -46.00  58.00   1.00    5.00    --  -11.59  19.00-150.00  104
  3  \w     -1.00  51.00   1.00    5.00    --   11.74 -99.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350772000
_diffrn_orient_matrix_UB_12      0.0186173000
_diffrn_orient_matrix_UB_13      -0.0395692000
_diffrn_orient_matrix_UB_21      -0.0194422000
_diffrn_orient_matrix_UB_22      -0.0321549000
_diffrn_orient_matrix_UB_23      -0.0263819000
_diffrn_orient_matrix_UB_31      -0.0161863000
_diffrn_orient_matrix_UB_32      -0.0016745000
_diffrn_orient_matrix_UB_33      0.0668521000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7169
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.613
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1152P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2387
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02205e2.cif
_cod_data_source_block           6_2
_cod_depositor_comments          'Adding full bibliography for 7241700.cif.'
_cod_database_code               7241700
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
3.a Free rotating group:
 O3(H3A,H3B)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C15(H15), C14(H14), C12(H12), C2(H2), C5(H5), C13(H13), C4(H4)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              81162
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.809
_oxdiff_exptl_absorpt_empirical_full_min 0.569