Convenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity
Tawfeek, Hendawy N.; Abdelmoez, Alshaimaa; Dahlous, Kholood A.; Youssif, Bahaa G. M.; Bräse, Stefan; Rissanen, Kari; Nieger, Martin; El-Sheref, Essmat M.; RSC Advances 14 (2024) 17866–17876; doi:10.1039/D4RA02531H

data_7248910
_publ_section_title
;
 Convenient synthesis and X-ray determination of
 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative
 activity
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              17866
_journal_page_last               17876
_journal_paper_doi               10.1039/D4RA02531H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 N3 S, Br'
_chemical_formula_sum            'C15 H14 Br N3 S'
_chemical_formula_weight         348.26
_chemical_name_systematic
;
5-phenyl-2-(phenylamino)-6H-1,3,4-thiadiazin-3-ium
;
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-01-30 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.364(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9077(1)
_cell_length_b                   9.1847(1)
_cell_length_c                   18.1367(2)
_cell_measurement_reflns_used    14033
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      78.8
_cell_measurement_theta_min      2.3
_cell_volume                     1481.29(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'omega scans, 0.5 deg.'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16484
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.309
_diffrn_reflns_theta_min         5.401
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       blocks
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00182(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0202
_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^)+(0.0219P)^2^+1.1270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             3177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02531h2.cif
_cod_data_source_block           sb1527_hy
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248910
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.459
_shelx_estimated_absorpt_t_max   0.558
_shelx_res_checksum              64130
_shelx_hkl_checksum              82703