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_7132364
_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            'C27 H35 Cl2 N O3 S'
_chemical_formula_weight         524.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.659(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5744(10)
_cell_length_b                   11.1460(10)
_cell_length_c                   23.328(2)
_cell_measurement_reflns_used    8905
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      57.15
_cell_measurement_theta_min      4.44
_cell_volume                     2710.5(4)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37115
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.995
_diffrn_reflns_theta_min         3.450
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 4256 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.071(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         10918
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0576P)^2^+0.9305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                10307
_reflns_number_total             10918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04815b2.cif
_cod_data_source_block           ga_221025e_a
_cod_depositor_comments
'Adding full bibliography for 7132361--7132365.cif.'
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7132364
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.685
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              49166
_shelx_hkl_checksum              82871