Iodine-dependent oxidative regioselective aminochalcogenation of indolines.
Zhang, Xiaoxiang; Liu, Chenrui; Wei, Wanxing; Zhang, Zhuan; Liang, Taoyuan; Chemical communications (Cambridge, England) 60 (2024) 1152–1155; doi:10.1039/d3cc05999e

data_7132580
_publ_section_title
;
 Iodine-dependent oxidative regioselective aminochalcogenation of
 indolines.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1152
_journal_page_last               1155
_journal_paper_doi               10.1039/d3cc05999e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H17 N3 S'
_chemical_formula_sum            'C19 H17 N3 S'
_chemical_formula_weight         319.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fgp8w
_audit_creation_date             2023-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-14 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.290(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7135(7)
_cell_length_b                   22.940(2)
_cell_length_c                   9.6284(11)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.5690
_cell_measurement_theta_min      4.2940
_cell_volume                     1676.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -1.00  71.00   0.80    1.00    --   15.81  57.00 -60.00   90
  2  \w      2.00  63.60   0.80    1.00    --   15.81  57.00  60.00   77
  3  \w     36.00  80.00   0.80    1.00    --   15.81 178.00-120.00   55
  4  \w     40.00  68.80   0.80    1.00    --   15.81 178.00 -30.00   36
  5  \w    -24.00  11.20   0.80    1.00    --  -16.59 -99.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127098000
_diffrn_orient_matrix_UB_12      0.0282096000
_diffrn_orient_matrix_UB_13      -0.0264702000
_diffrn_orient_matrix_UB_21      -0.0066481000
_diffrn_orient_matrix_UB_22      0.0122265000
_diffrn_orient_matrix_UB_23      0.0665081000
_diffrn_orient_matrix_UB_31      0.0924291000
_diffrn_orient_matrix_UB_32      -0.0030129000
_diffrn_orient_matrix_UB_33      0.0219624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8754
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.440
_diffrn_reflns_theta_min         3.553
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0707
_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^)+(0.0754P)^2^+0.4195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2404
_reflns_number_total             3848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05999e2.cif
_cod_data_source_block           exp_12703
_cod_depositor_comments          'Adding full bibliography for 7132580.cif.'
_cod_original_cell_volume        1676.4(3)
_cod_database_code               7132580
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C15(H15), C9(H9), C12(H12), C19(H19), C11(H11), C5(H5), C16(H16), C18(H18),
 C3(H3), C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              27723
_shelx_hkl_checksum              49847
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.577
_oxdiff_exptl_absorpt_empirical_full_min 0.658