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_4038937
_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         'C17 H14 N4 O5 S'
_chemical_formula_sum            'C17 H14 N4 O5 S'
_chemical_formula_weight         386.38
_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             2017-05-30
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.45(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.210(6)
_cell_length_b                   7.242(6)
_cell_length_c                   26.864(15)
_cell_measurement_reflns_used    7301
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      65.1645
_cell_measurement_theta_min      3.3041
_cell_volume                     1970(2)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21371
_diffrn_reflns_theta_full        65.66
_diffrn_reflns_theta_max         65.65
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  1.24538
_exptl_absorpt_correction_T_min  0.71645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0011(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   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0920P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2563
_reflns_number_total             3397
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3ag.CIF
_cod_data_source_block           dc
_cod_database_code               4038937