Direct C(sp3)–H acyloxylation of indolin-3-ones with carboxylic acids catalysed by KI
Zhao, Yong-Long; Tang, Yong-Qin; Fei, Xing-Hai; Yang, Fen-Fen; Cao, Zhuo-Xian; Duan, Dong-Zhu; Zhao, Qing-Jie; Yang, Yuan-Yong; Zhou, Meng; He, Bin; Green Chemistry 22 (2020) 2354–2358; doi:10.1039/C9GC04446A

data_7240053
_publ_section_title
;
 Direct C(sp3)--H acyloxylation of indolin-3-ones with carboxylic acids
 catalysed by KI
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2354
_journal_page_last               2358
_journal_paper_doi               10.1039/C9GC04446A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc232y5b
_audit_creation_date             2019-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-08 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.02(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.4606(4)
_cell_length_b                   16.9137(8)
_cell_length_c                   35.129(3)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.6700
_cell_measurement_theta_min      2.0970
_cell_volume                     5027.0(5)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -72.00  12.00   1.00    5.00    --  -11.59 -77.00 -30.00   84
  2  \w    -17.00  34.00   1.00    5.00    --   11.74 -57.00-180.00   51
  3  \w    -46.00 -15.00   1.00    5.00    --  -11.43 -57.00-180.00   31
  4  \w    -83.00 -32.00   1.00    5.00    --  -11.43 -37.00  60.00   51
;
_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      -0.0510207000
_diffrn_orient_matrix_UB_12      -0.0095179000
_diffrn_orient_matrix_UB_13      -0.0154351000
_diffrn_orient_matrix_UB_21      -0.0660929000
_diffrn_orient_matrix_UB_22      0.0030737000
_diffrn_orient_matrix_UB_23      0.0122317000
_diffrn_orient_matrix_UB_31      -0.0069223000
_diffrn_orient_matrix_UB_32      0.0407320000
_diffrn_orient_matrix_UB_33      -0.0045032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            24168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.115
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71830
_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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     688
_refine_ls_number_reflns         8834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+3.2254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6349
_reflns_number_total             8834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc04446a2.cif
_cod_data_source_block           guiz0706
_cod_depositor_comments
;Adding full bibliography for 7240053.cif.

 Adding full bibliography for 7240053.cif.
;
_cod_original_cell_volume        5026.9(5)
_cod_database_code               7240053
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.60
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C4(H4), C12(H12), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C17(H17A,H17B,
 H17C)
;
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.718