X-ray crystallographic structure of a novel enantiopure chiral isothiourea with potential applications in enantioselective synthesis
Savin, J. Alejandro; Ávila-Ortíz, C. Gabriela; Leyva-Ramírez, Marco Antonio; Juaristi, Eusebio; Acta Crystallographica Section C Structural Chemistry 80 (2024) 15–20; doi:10.1107/S2053229623010781

data_2022997
_publ_section_title
;
 X-ray crystallographic structure of a novel enantiopure chiral
 isothiourea with potential applications in enantioselective synthesis
;
_journal_coeditor_code           ZO3043
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_page_first              15
_journal_page_last               20
_journal_paper_doi               10.1107/S2053229623010781
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C15 H17 N2 S +, Br -'
_chemical_formula_moiety         'C15 H17 N2 S +, Br -'
_chemical_formula_sum            'C15 H17 Br N2 S'
_chemical_formula_weight         337.27
_chemical_name_systematic
'(4a<i>R</i>,8a<i>R</i>)-3-Phenyl-4a,5,6,7,8,8a-hexahydrobenzo[4,5]imidazo[2,1-<i>b</i>]thiazol-9-ium bromide'
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9846(6)
_cell_length_b                   9.1982(6)
_cell_length_c                   19.3636(16)
_cell_measurement_reflns_used    9613
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.45
_cell_volume                     1422.14(18)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX4 (Bruker, 2016)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            97564
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.146
_diffrn_reflns_theta_min         2.451
_diffrn_source                   'microsource x-ray tube'
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.65
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.038(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.0920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                3648
_reflns_number_total             4178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zo3043sup1.cif
_cod_data_source_block           I
_cod_database_code               2022997
_shelx_estimated_absorpt_t_min   0.343
_shelx_estimated_absorpt_t_max   0.66
_shelx_hkl_checksum              27671
_shelx_res_checksum              32509
_cod_database_fobs_code 2022997