Chiral imidazolium receptors for citrate and malate: the importance of the preorganization.
Faggi, Enrico; Porcar, Raúl; Bolte, Michael; Luis, Santiago V.; García-Verdugo, Eduardo; Alfonso, Ignacio; The Journal of organic chemistry 79 (2014) 9141–9149; doi:10.1021/jo5014977

data_4029932
_publ_section_title
;
 Chiral imidazolium receptors for citrate and malate: the importance of
 the preorganization.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9141
_journal_page_last               9149
_journal_paper_doi               10.1021/jo5014977
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H36 N4 O2, 2(Br)'
_chemical_formula_sum            'C26 H36 Br2 N4 O2'
_chemical_formula_weight         596.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 110.206(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.4217(18)
_cell_length_b                   7.2389(4)
_cell_length_c                   8.3178(6)
_cell_measurement_reflns_used    18646
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.05
_cell_measurement_theta_min      2.61
_cell_volume                     1323.47(17)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9352
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.609
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    3.093
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
; 
 Flack x determined using 1296 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.029(14)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0731P)^2^+0.3476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2932
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5014977_si_002.cif
_cod_data_source_block           nacho14
_cod_depositor_comments
'Adding full bibliography for 4029931--4029932.cif.'
_cod_original_cell_volume        1323.47(16)
_cod_database_code               4029932
_shelx_estimated_absorpt_t_min   0.489
_shelx_estimated_absorpt_t_max   0.913
_shelxl_version_number           2014-1
_shelx_res_checksum              59994