Selective halocyclization and iodosulfonylation of N-benzothiazol2-yl alkynamides under mild conditions
Fang, Yu; Ren, Shangfeng; He, Chen; Han, Huiqi; Liao, Fuming; Liu, Jin-Biao; Yang, Min; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01165D

data_7158803
_publ_section_title
;
 Selective halocyclization and iodosulfonylation of N-benzothiazol2-yl
 alkynamides under mild conditions
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01165D
_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
_audit_creation_date             2021-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-28 deposited with the CCDC.	2022-07-29 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    293(2)
_cell_measurement_theta_max      28.8430
_cell_measurement_theta_min      3.4940
_cell_volume                     2893.7(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.838
_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            13012
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.999
_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_crystal_density_diffrn    1.856
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.249
_refine_diff_density_min         -1.349
_refine_diff_density_rms         0.117
_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     379
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4707
_reflns_number_total             6790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01165d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H18 I2 N4 O2 S2'
_cod_original_formula_weight         808.42
_cod_original_formula_moiety         '2(C16 H9 I N2 O S)'
_cod_original_formula_units_Z            4
_cod_database_code               7158803
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.625
_shelx_estimated_absorpt_t_min   0.602
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C31(H31), C24(H24), C23(H23), C22(H22), C18(H18), C17(H17), C16(H16),
 C13(H13), C10(H10), C9(H9), C8(H8), C7(H7), C6(H6), C5(H5), C4(H4), C2(H2),
 C1(H1), C35(H35)
;
_olex2_submission_special_instructions 'No special instructions were received'