Crystallographic evidence for unintended benzisothiazolinone 1-oxide formation from benzothiazinones through oxidation
Eckhardt, Tamira; Goddard, Richard; Lehmann, Christoph; Richter, Adrian; Sahile, Henok Asfaw; Liu, Rui; Tiwari, Rohit; Oliver, Allen G.; Miller, Marvin J.; Seidel, Rüdiger W.; Imming, Peter; Acta Crystallographica Section C 76 (2020) –; doi:10.1107/S2053229620010931

data_2022238
_publ_section_title
;
 Crystallographic evidence for unintended benzisothiazolinone 1-oxide
 formation from benzothiazinones through oxidation
;
_journal_coeditor_code           EP3008
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620010931
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C14 H12 F3 N3 O5 S'
_chemical_formula_moiety         'C14 H12 F3 N3 O5 S'
_chemical_formula_sum            'C14 H12 F3 N3 O5 S'
_chemical_formula_weight         391.33
_chemical_name_systematic
'7-Nitro-2-(piperidine-1-carbonyl)-5-(trifluoromethyl)benzo[<i>d</i>]isothiazol-3(2<i>H</i>)-one 1-oxide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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                   17.6719(8)
_cell_length_b                   25.7296(12)
_cell_length_c                   6.8887(3)
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      47.8671
_cell_measurement_theta_min      3.0334
_cell_volume                     3132.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018)
;
_computing_publication_material
;
enCIFer (Allen <i>et al.</i>,  2004) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker Kappa Mach3 APEXII'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22457
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.097
_diffrn_reflns_theta_min         3.034
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.93571
_exptl_absorpt_correction_T_min  0.74769
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.749
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0581P)^2^+17.2243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                1843
_reflns_number_total             2477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ep3008sup1.cif
_cod_data_source_block           3
_cod_database_code               2022238
_shelx_estimated_absorpt_t_min   0.596
_shelx_estimated_absorpt_t_max   0.907
_shelx_hkl_checksum              3400
_shelx_res_checksum              12117
_cod_database_fobs_code 2022238