Selective C-H Acylation of Indoles with α-Oxocarboxylic Acids at the C4-Position by Palladium Catalysis
Zhang, Jitan; Wu, Manyi; Fan, Jian; Xu, Qiaoqiao; Xie, Meihua; Chemical Communications  (2019) –; doi:10.1039/C9CC03893K

data_7123689
_publ_section_title
;
 Selective C-H Acylation of Indoles with \a-Oxocarboxylic Acids at the
 C4-Position by Palladium Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03893K
_journal_year                    2019
_chemical_formula_moiety         'C29 H20 F N O4 S'
_chemical_formula_sum            'C29 H20 F N O4 S'
_chemical_formula_weight         497.52
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-13 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8851(5)
_cell_length_b                   14.7661(7)
_cell_length_c                   14.9956(7)
_cell_measurement_reflns_used    9653
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.10
_cell_volume                     2742.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21724
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.808
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1870
_refine_ls_R_factor_gt           0.1182
_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^)+(0.1572P)^2^+1.0739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2800
_refine_ls_wR_factor_ref         0.3161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2526
_reflns_number_total             4790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03893k2.cif
_cod_data_source_block           20180930a
_cod_database_code               7123689
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.965
_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 Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C28(H28), C4(H4), C18(H18), C13(H13), C12(H12), C25(H25),
 C3(H3), C7(H7), C29(H29), C21(H21), C14(H14), C20(H20), C22(H22), C26(H26),
 C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              38667
_shelx_fab_checksum              68772
_olex2_submission_special_instructions 'No special instructions were received'