Synthesis and crystal structures of halogenated oxathiazolones and an unexpected propanamide.
George, Tanner; McWilliams, Samantha W.; Masuda, Jason D.; Schriver, Melbourne J.; Acta crystallographica. Section C, Structural chemistry 79 (2023) 125–132; doi:10.1107/S2053229623002152

data_2022706
_publ_section_title
;
 Synthesis and crystal structures of halogenated oxathiazolones and an
 unexpected propanamide.
;
_journal_coeditor_code           DV3021
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              125
_journal_page_last               132
_journal_paper_doi               10.1107/S2053229623002152
_journal_volume                  79
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_iupac          'C3 H4 Br2 Cl N O'
_chemical_formula_moiety         'C3 H4 Br2 Cl N O'
_chemical_formula_sum            'C3 H4 Br2 Cl N O'
_chemical_formula_weight         265.34
_chemical_name_systematic
;
<i>rac</i>-2,3-Dibromo-3-chloropropanamide
;
_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
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.5967(2)
_cell_length_b                   24.1942(9)
_cell_length_c                   9.1724(3)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      3.20
_cell_volume                     1463.12(8)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009),
<i>ORTEP-3 for Windows</i> (Farrugia, 2012) and
Mercury (Macrae <i>et al.</i>, 2020)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100.00
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            55465
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    11.355
_exptl_absorpt_correction_T_max  0.0202
_exptl_absorpt_correction_T_min  0.0028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.146
_refine_diff_density_min         -1.086
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6456
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0815P)^2^+6.1207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                5710
_reflns_number_total             6456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dv3021sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2022705--2022707.cif.'
_cod_database_code               2022706
_cod_database_fobs_code          2022706
_shelx_estimated_absorpt_t_min   0.143
_shelx_estimated_absorpt_t_max   0.428
_shelx_hkl_checksum              92128
_shelx_res_checksum              66753