Structural diversity in imidazolidinone organocatalysts: a synchrotron and computational study
Burley, Jonathan C.; Gilmour, Ryan; Prior, Timothy J.; Day, Graeme M.; Acta Crystallographica Section C 64 (2008) o10–o14; doi:10.1107/S0108270107051396

data_2016404
_publ_section_title
;
 Structural diversity in imidazolidinone organocatalysts: a synchrotron
 and computational study
;
_journal_coeditor_code           SF3055
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o10
_journal_page_last               o14
_journal_paper_doi               10.1107/S0108270107051396
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H19 N2 O +, Cl -, H2 O'
_chemical_formula_moiety         'C13 H19 N2 O +, Cl -, H2 O'
_chemical_formula_sum            'C13 H21 Cl N2 O2'
_chemical_formula_weight         272.77
_chemical_name_common            'S enantiomer'
_chemical_name_systematic
;
(S)-5-benzyl-2,2,3-trimethyl-4-oxoimidazolidin-1-ium chloride monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.796(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6425(14)
_cell_length_b                   7.0517(10)
_cell_length_c                   11.0895(16)
_cell_measurement_reflns_used    914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      3.68
_cell_volume                     725.57(18)
_computing_cell_refinement       'APEXII (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'APEXII (Bruker, 2004)'
_computing_molecular_graphics    'WinGX (Version 1.64; Farrugia, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frame'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS, Station 16.2SMX'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.79770
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6377
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         32.43
_diffrn_reflns_theta_min         3.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square plate'
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.378
_refine_ls_abs_structure_details 'Flack (1983), 1339 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2438
_reflns_number_total             3330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sf3055.cif
_cod_data_source_block           S4
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               2016404