“Doubly enantiophobic” behavior during crystallization of racemic 1,5-dihydro-2H-pyrrol-2-one thioether
Lodochnikova, Olga A.; Zaripova, Aigul R.; Fayzullin, Robert R.; Samigullina, Aida I.; Vandyukova, Irina I.; Potapova, Lubov N.; Kurbangalieva, Almira R.; CrystEngComm 20 (2018) 3218–; doi:10.1039/C8CE00369F

data_7230567
_publ_section_title
;
 &#x201C;Doubly enantiophobic&#x201D; behavior during crystallization of
 racemic 1,5-dihydro-2H-pyrrol-2-one thioether
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3218
_journal_paper_doi               10.1039/C8CE00369F
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Br2 N O2 S'
_chemical_formula_sum            'C17 H13 Br2 N O2 S'
_chemical_formula_weight         455.16
_chemical_melting_point          434
_chemical_name_systematic
rac-1-benzyl-3-bromo-4-[(4-bromophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-11-28 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.643(2)
_cell_length_b                   9.643(2)
_cell_length_c                   32.282(8)
_cell_measurement_reflns_used    4703
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.28
_cell_measurement_theta_min      2.44
_cell_volume                     2599.7(10)
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2015.9-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            19163
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.805
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method 'from hot acetone solution'
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     233
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0628P)^2^+1.8304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2513
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00369f1.cif
_cod_data_source_block           aigul28
_cod_depositor_comments
'Adding full bibliography for 7230567--7230568.cif.'
_cod_original_cell_volume        2599.7(14)
_cod_database_code               7230567
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.163
_shelx_estimated_absorpt_t_max   0.718
_shelx_res_checksum              17901