Pyridinium 1,4-Zwitterionic Thiolates as a useful Class of Sulfur-containing Synthons: Application to the Synthesis of 2,5-Dihydro-1,4,5-thiadiazepines
Cheng, Bin; Li, Yuntong; Wang, Taimin; Zhang, Xinping; Li, Hui; Li, Yun; Zhai, HB; Chemical Communications  (2019) –; doi:10.1039/C9CC08326J

data_7124455
_publ_section_title
;
 Pyridinium 1,4-Zwitterionic Thiolates as a useful Class of
 Sulfur-containing Synthons: Application to the Synthesis of
 2,5-Dihydro-1,4,5-thiadiazepines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC08326J
_journal_year                    2019
_chemical_formula_moiety         'C16 H16 N2 O7 S'
_chemical_formula_sum            'C16 H16 N2 O7 S'
_chemical_formula_weight         380.37
_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     direct
_audit_creation_date             2017-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-12-30 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.108(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1191(7)
_cell_length_b                   26.9873(15)
_cell_length_c                   7.2702(5)
_cell_measurement_reflns_used    1167
_cell_measurement_temperature    292.46(10)
_cell_measurement_theta_max      24.6590
_cell_measurement_theta_min      3.9140
_cell_volume                     1727.4(2)
_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      292.46(10)
_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  -97.00  -59.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -180.0000 25

  2 omega  -27.00   54.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  120.0000 54

  3 omega  -15.00   90.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  150.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0783122000
_diffrn_orient_matrix_UB_12      0.0001686000
_diffrn_orient_matrix_UB_13      0.0484690000
_diffrn_orient_matrix_UB_21      -0.0139595000
_diffrn_orient_matrix_UB_22      0.0184498000
_diffrn_orient_matrix_UB_23      0.0628203000
_diffrn_orient_matrix_UB_31      -0.0128043000
_diffrn_orient_matrix_UB_32      -0.0187474000
_diffrn_orient_matrix_UB_33      0.0624595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6354
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.544
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86233
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.3533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2257
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08326j2.cif
_cod_data_source_block           liyt_2_90_3
_cod_database_code               7124455
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              97183
_olex2_date_sample_data_collection 2017-10-13
_olex2_submission_special_instructions 'No special instructions were received'