Design of Benzoxathiazin-3-one 1,1-Dioxides as a New Class of Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely Selective PNPLA4 Inhibitor.
Kornahrens, Anne F.; Cognetta, 3rd, Armand B; Brody, Daniel M.; Matthews, Megan L.; Cravatt, Benjamin F.; Boger, Dale L.; Journal of the American Chemical Society 139 (2017) 7052–7061; doi:10.1021/jacs.7b02985

data_4126138
_publ_section_title
;
 Design of Benzoxathiazin-3-one 1,1-Dioxides as a New Class of
 Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely
 Selective PNPLA4 Inhibitor.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7052
_journal_page_last               7061
_journal_paper_doi               10.1021/jacs.7b02985
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C14 H12 N2 O3 S'
_chemical_formula_weight         288.32
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.551(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.916(3)
_cell_length_b                   7.5579(17)
_cell_length_c                   25.872(5)
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.81
_cell_volume                     2490.6(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11508
_diffrn_reflns_point_group_measured_fraction_full 0.771
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.735
_diffrn_reflns_theta_min         1.596
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.945
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
; 
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.51(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         6994
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0849
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2263
_reflns_Friedel_coverage         0.520
_reflns_Friedel_fraction_full    0.542
_reflns_Friedel_fraction_max     0.503
_reflns_number_gt                4820
_reflns_number_total             6994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02985_si_002.cif
_cod_data_source_block           boger08
_cod_original_cell_volume        2490.5(9)
_cod_database_code               4126138
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-3
_shelx_res_checksum              85433
_shelx_hkl_checksum              24005