Acid-Catalyzed Hydrolysis and Intramolecular Cyclization of <i>N</i>-Cyano Sulfoximines for the Synthesis of Thiadiazine 1-Oxides.
Oh, In Seok; Seo, Ye Ji; Hyun, Ji Young; Lim, Hwan Jung; Lee, Duck-Hyung; Park, Seong Jun; ACS omega 7 (2022) 2160–2169; doi:10.1021/acsomega.1c05570

data_4519312
_publ_section_title
;
 Acid-Catalyzed Hydrolysis and Intramolecular Cyclization of
 <i>N</i>-Cyano Sulfoximines for the Synthesis of Thiadiazine 1-Oxides.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              2160
_journal_page_last               2169
_journal_paper_doi               10.1021/acsomega.1c05570
_journal_volume                  7
_journal_year                    2022
_chemical_formula_sum            'C13 H11 N3 O S'
_chemical_formula_weight         257.31
_chemical_name_common            S-216
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9488(6)
_cell_length_b                   12.8366(7)
_cell_length_c                   18.5222(11)
_cell_measurement_reflns_used    7908
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.4747
_cell_measurement_theta_min      2.1991
_cell_volume                     2365.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'f and w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         2.199
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 2141 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5193
_reflns_number_total             6093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05570_si_001.cif
_cod_data_source_block           20210817LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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_database_code               4519312
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              5601
_shelx_hkl_checksum              13913