Regioselective C7 sulfinylation of 4-aminoindoles with sulfinates.
Zhang, Yun; Zhang, Zhehao; He, Yong-Ke; Zhang, Jun; Wu, Jie; Chemical communications (Cambridge, England) 61 (2025) 14689–14692; doi:10.1039/d5cc03623b

data_1575488
_publ_section_title
;
 Regioselective C7 sulfinylation of 4-aminoindoles with sulfinates.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14689
_journal_page_last               14692
_journal_paper_doi               10.1039/d5cc03623b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H13 F3 N2 O S'
_chemical_formula_sum            'C16 H13 F3 N2 O S'
_chemical_formula_weight         338.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-05-05 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                105.643(7)
_cell_angle_beta                 97.748(7)
_cell_angle_gamma                104.859(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6256(9)
_cell_length_b                   9.9455(12)
_cell_length_c                   11.2468(12)
_cell_measurement_reflns_used    5113
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.60
_cell_measurement_theta_min      6.64
_cell_volume                     774.61(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 0.966
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8016
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.598
_diffrn_reflns_theta_min         6.644
_exptl_absorpt_coefficient_mu    2.210
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1640 before and 0.0820 after correction.
The Ratio of minimum to maximum transmission is 0.4667.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0558
_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^)+(0.1017P)^2^+0.1417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2405
_reflns_number_total             2746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03623b2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1575487--1575488.cif.'
_cod_original_cell_volume        774.60(16)
_cod_database_code               1575488
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C5(H5), C15(H15), C10(H10), C4(H4), C1(H1A), C14(H14),
  C2(H2A), C3(H3)
;
_shelx_res_checksum              52137
_shelx_hkl_checksum              82860
_olex2_submission_special_instructions 'No special instructions were received'