Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of Benzopyridothiazepines and Benzothiophenes.
Cheng, Bin; Li, Yuntong; Wang, Taimin; Zhang, Xinping; Li, Hui; He, YiXuan; Li, Yun; Zhai, Hongbin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00374

data_4038335
_publ_section_title
;
 Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of
 Benzopyridothiazepines and Benzothiophenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00374
_journal_year                    2020
_chemical_formula_moiety         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.990(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9495(13)
_cell_length_b                   10.4491(10)
_cell_length_c                   17.3052(17)
_cell_measurement_reflns_used    1154
_cell_measurement_temperature    286(4)
_cell_measurement_theta_max      23.6520
_cell_measurement_theta_min      3.6900
_cell_volume                     1972.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      286(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -12.00   26.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2711  -99.0000  -60.0000 38

  2 omega   45.00  102.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000  -90.0000 57

  3 omega   17.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000  -60.0000 52

  4 omega  -31.00   60.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -19.0000  -90.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0471710000
_diffrn_orient_matrix_UB_12      0.0136729000
_diffrn_orient_matrix_UB_13      0.0296367000
_diffrn_orient_matrix_UB_21      0.0092370000
_diffrn_orient_matrix_UB_22      -0.0664425000
_diffrn_orient_matrix_UB_23      0.0064328000
_diffrn_orient_matrix_UB_31      0.0438375000
_diffrn_orient_matrix_UB_32      -0.0006258000
_diffrn_orient_matrix_UB_33      -0.0278256000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7545
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049
_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     255
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.3563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                2257
_reflns_number_total             3875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00374_si_002.cif
_cod_data_source_block           liyt_0627
_cod_database_code               4038335
_reflns_odcompleteness_completeness 99.58
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_olex2_date_sample_data_collection 2018-06-28
_olex2_submission_special_instructions 'No special instructions were received'