Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides
Ilkin, Vladimir; Berseneva, Vera; Beryozkina, Tetyana; Glukhareva, Tatiana; Dianova, Lidia; Dehaen, Wim; Seliverstova, Eugenia; Bakulev, Vasiliy; Beilstein Journal of Organic Chemistry 16 (2020) 2937–2947; doi:10.3762/bjoc.16.243

data_4038938
_publ_section_title
;
 Regioselective synthesis of heterocyclic N-sulfonyl amidines from
 heteroaromatic thioamides and sulfonyl azides
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2937
_journal_page_last               2947
_journal_paper_doi               10.3762/bjoc.16.243
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 N7 O5 S, C4 H8 O2'
_chemical_formula_sum            'C23 H27 N7 O7 S'
_chemical_formula_weight         545.58
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.171(6)
_cell_angle_beta                 96.461(6)
_cell_angle_gamma                109.787(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4172(8)
_cell_length_b                   11.4155(10)
_cell_length_c                   13.0409(9)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9080
_cell_measurement_theta_min      3.6240
_cell_volume                     1290.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0735
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12205
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.2221
_reflns_number_gt                3512
_reflns_number_total             6994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3t.CIF
_cod_data_source_block           exp_701
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1290.72(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4038938