Selective halocyclization and iodosulfonylation of <i>N</i>-benzothiazol-2-yl alkynamides under mild conditions.
Fang, Yu; Ren, Shangfeng; He, Chen; Han, Huiqi; Liu, Jin-Biao; Liao, Fumin; Yang, Min; Organic & biomolecular chemistry 20 (2022) 6550–6553; doi:10.1039/d2ob01165d

data_7158863
_publ_section_title
;
 Selective halocyclization and iodosulfonylation of
 <i>N</i>-benzothiazol-2-yl alkynamides under mild conditions.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6550
_journal_page_last               6553
_journal_paper_doi               10.1039/d2ob01165d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C16 H9 I N2 O S'
_chemical_formula_sum            'C16 H9 I N2 O S'
_chemical_formula_weight         404.21
_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_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.434(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9343(14)
_cell_length_b                   7.2169(5)
_cell_length_c                   20.7700(14)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      28.8430
_cell_measurement_theta_min      3.4940
_cell_volume                     2893.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.839
_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      4.00  48.00   1.00    3.31    --   16.20 -99.00-120.00   44
  2  \w     48.00  83.00   1.00    3.31    --   16.20  57.00 -90.00   35
  3  \w    -46.00  85.00   1.00    3.31    --   16.20   0.00 -90.00  131
;
_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      -0.0212653000
_diffrn_orient_matrix_UB_12      -0.0477529000
_diffrn_orient_matrix_UB_13      -0.0274576000
_diffrn_orient_matrix_UB_21      -0.0294899000
_diffrn_orient_matrix_UB_22      0.0188793000
_diffrn_orient_matrix_UB_23      0.0122685000
_diffrn_orient_matrix_UB_31      -0.0055040000
_diffrn_orient_matrix_UB_32      0.0837062000
_diffrn_orient_matrix_UB_33      -0.0184178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.999
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.00255(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+1.4883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4708
_reflns_number_total             6791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01165d2.cif
_cod_data_source_block           20211112
_cod_database_code               7158863
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H O N I'
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.663
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
;
_shelx_res_checksum              21061
_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.612