Synthesis of novel 1,2,4-thiadiazinane 1,1-dioxides via three component SuFEx type reaction
Khumalo, Mzilikazi F.; Akpan, Ekemini D.; Chinthakindi, Praveen K.; Brasil, Edikarlos M.; Rajbongshi, Kamal K.; Makatini, Maya M.; Govender, Thavendran; Kruger, Hendrik G.; Naicker, Tricia; Arvidsson, Per I.; RSC Advances 8 (2018) 37503–; doi:10.1039/C8RA07627H

data_7231778
_publ_section_title
;
 Synthesis of novel 1,2,4-thiadiazinane 1,1-dioxides via three component
 SuFEx type reaction
;
_journal_issue                   65
_journal_name_full               'RSC Advances'
_journal_page_first              37503
_journal_paper_doi               10.1039/C8RA07627H
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C20 H19 F N2 O2 S, 0.5(C7 H8)'
_chemical_formula_sum            'C23.5 H23 F N2 O2 S'
_chemical_formula_weight         416.50
_chemical_name_systematic
'2-(4-fluorophenyl)-<i>N</i>-phenyl-2-(phenylamino)ethanesulfonamide -- toluene (1/0.5)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-10-07 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.009(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.2594(19)
_cell_length_b                   5.7351(4)
_cell_length_c                   26.1139(18)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.06
_cell_volume                     3993.2(5)
_computing_cell_refinement       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_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-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            24448
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_min         1.965
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           20
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752
_exptl_crystal_recrystallization_method
'The material was recrystallised from Toluene by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0457P)^2^+4.7044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4259
_reflns_number_total             5003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07627h2.cif
_cod_data_source_block           18zs_ggkm_c1_0m
_cod_original_formula_sum        'C23.50 H23 F N2 O2 S'
_cod_database_code               7231778
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.942
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C22
 1.51 with sigma of 0.02
 C22-C23 \\sim C23-C24 \\sim C24-C25 \\sim C25-C26 \\sim C26-C27 \\sim C27-C22
 with sigma of 0.02
 C22-C26 \\sim C22-C24 \\sim C27-C25 \\sim C23-C27 \\sim C24-C26 \\sim C23-C25
 with sigma of 0.04
 C21-C27 \\sim C21-C23
 with sigma of 0.04
3. Restrained planarity
 C21, C22, C23, C24, C25, C26, C27
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 C21, C22, C23, C24, C25, C26, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C24, C21, C22, C23, C27, C26, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) C22(0.5) C23(0.5) H23(0.5)
 C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5) H27(0.5)
7.a Riding coordinates:
 N1(H1)
7.b Ternary CH refined with riding coordinates:
 C8(H8)
7.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
7.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C3(H3), C2(H2A), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
7.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              88020
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;