An electrostatically enhanced bifunctional enantioselective thiourea catalyst.
Nisly, Josiah K.; Kass, Steven R.; Organic & biomolecular chemistry 24 (2026) 1369–1378; doi:10.1039/d5ob01845e

data_7160925
_publ_section_title
;
 An electrostatically enhanced bifunctional enantioselective thiourea
 catalyst.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1369
_journal_page_last               1378
_journal_paper_doi               10.1039/d5ob01845e
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H25 N4 S, I'
_chemical_formula_sum            'C15 H25 I N4 S'
_chemical_formula_weight         420.35
_chemical_name_systematic
; 
'3-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1-methylpyridin-1-ium iodide' 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3559(3)
_cell_length_b                   9.8324(4)
_cell_length_c                   24.4571(11)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.66
_cell_volume                     1768.89(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution
'SHELXT, Sheldrick, G. M. Acta Cryst. (2015) A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon-III CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.618
_diffrn_reflns_theta_min         2.232
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    1.929
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS, Krause, L. et al. J. Appl. Cryst. (2015), 48, 3-10.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6503
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 2267 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.024(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0151
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0125P)^2^+0.4990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0342
_refine_ls_wR_factor_ref         0.0344
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5356
_reflns_number_total             5450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01845e2.cif
_cod_data_source_block           24016b_a
_cod_database_code               7160925
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.723
_shelx_estimated_absorpt_t_max   0.910
_shelx_res_checksum              86068