Cascade alkyl migration in 2-alkynylanilines for the synthesis of benzenoid ring multi-functionalized indoles.
He, Jiwen; Li, Xiaohua; He, Qiuqin; Fan, Renhua; Chemical communications (Cambridge, England) 60 (2023) 71–74; doi:10.1039/d3cc04815b

data_7132361
_publ_section_title
;
 Cascade alkyl migration in 2-alkynylanilines for the synthesis of
 benzenoid ring multi-functionalized indoles.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              71
_journal_page_last               74
_journal_paper_doi               10.1039/d3cc04815b
_journal_volume                  60
_journal_year                    2023
_chemical_formula_sum            'C26 H25 N O3 S'
_chemical_formula_weight         431.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5963(5)
_cell_length_b                   8.0239(2)
_cell_length_c                   17.6239(5)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      56.94
_cell_measurement_theta_min      4.93
_cell_volume                     2205.51(11)
_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'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28059
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.496
_diffrn_reflns_theta_min         4.934
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1781 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.055(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0343P)^2^+0.2721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4038
_reflns_number_total             4371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04815b2.cif
_cod_data_source_block           ga_210720ca_a
_cod_depositor_comments
'Adding full bibliography for 7132361--7132365.cif.'
_cod_database_code               7132361
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.849
_shelx_estimated_absorpt_t_max   0.916
_shelx_res_checksum              27739
_shelx_hkl_checksum              80707