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_2022239
_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_absolute_configuration rmad
_chemical_formula_iupac          'C17 H16 F3 N3 O7 S'
_chemical_formula_moiety         'C17 H16 F3 N3 O7 S'
_chemical_formula_sum            'C17 H16 F3 N3 O7 S'
_chemical_formula_weight         463.39
_chemical_name_systematic
'2-[(<i>S</i>)-2-Methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carbonyl]-7-nitro-5-(trifluoromethyl)benzo[<i>d</i>]isothiazol-3(2<i>H</i>)-one 1-oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.0022(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8165(2)
_cell_length_b                   16.1649(4)
_cell_length_c                   13.4246(3)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.30
_cell_measurement_theta_min      3.29
_cell_volume                     1913.25(8)
_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      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36857
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.342
_diffrn_reflns_theta_min         3.292
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    2.227
_exptl_absorpt_correction_T_max  0.9488
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       blade
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.312
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 3080 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.017(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7140
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0446P)^2^+0.5798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                6860
_reflns_number_total             7140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ep3008sup1.cif
_cod_data_source_block           4
_cod_original_cell_volume        1913.24(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022239
_cod_database_fobs_code          2022239
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.920
_shelx_hkl_checksum              18963
_shelx_res_checksum              94818