Comparison between the crystal structures of racemic and enantiopure aryl benzyl sulfoxides.
Capozzi, Maria Annunziata M.; Alvarez-Larena, Angel; Piniella Febrer, Joan F.; Cardellicchio, Cosimo; RSC advances 15 (2025) 37824–37832; doi:10.1039/d5ra06476g

data_7251031
_publ_section_title
;
 Comparison between the crystal structures of racemic and enantiopure aryl
 benzyl sulfoxides.
;
_journal_issue                   45
_journal_name_full               'RSC advances'
_journal_page_first              37824
_journal_page_last               37832
_journal_paper_doi               10.1039/d5ra06476g
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C13 H10 Br N O3 S'
_chemical_formula_sum            'C13 H10 Br N O3 S'
_chemical_formula_weight         340.19
_chemical_name_systematic
;
4-bromophenyl 2-nitrobenzyl sulfoxide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2025-07-23 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5989(5)
_cell_length_b                   13.6591(8)
_cell_length_c                   13.3151(8)
_cell_measurement_reflns_used    4061
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.29
_cell_measurement_theta_min      2.89
_cell_volume                     1360.50(15)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10688
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.761
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.177
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.8350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2406
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra06476g2.cif
_cod_data_source_block           kc11
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251031
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.289
_shelx_estimated_absorpt_t_max   0.584
_shelx_res_checksum              800