An interrupted Heyns rearrangement approach to regioselective synthesis of acylindoles
Altia, Minakshi; Anbarasan, Pazhamalai; Chemical Communications  (2023) –; doi:10.1039/D3CC04144A

data_7132260
_publ_section_title
;
 An interrupted Heyns rearrangement approach to regioselective synthesis
 of acylindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04144A
_journal_year                    2023
_chemical_formula_moiety         'C21 H14 Br N O'
_chemical_formula_sum            'C21 H14 Br N O'
_chemical_formula_weight         376.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-07-29 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.203(2)
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_cell_angle_gamma                103.107(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6408(5)
_cell_length_b                   9.9341(5)
_cell_length_c                   10.3685(5)
_cell_measurement_reflns_used    5672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.49
_cell_volume                     834.05(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12302
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.041
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0127(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0382P)^2^+0.3547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             2924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04144a2.cif
_cod_data_source_block           958
_cod_database_code               7132260
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.756
_shelx_res_checksum              77492
_shelx_hkl_checksum              66798