Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation-π Interactions.
Simó Padial, Joan; Poater, Jordi; Nguyen, D. Thao; Tinnemans, Paul; Bickelhaupt, F. Matthias; Mecinović, Jasmin; The Journal of organic chemistry 82 (2017) 9418–9424; doi:10.1021/acs.joc.7b01406

data_4033070
_publ_section_title
;
 Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation-\p
 Interactions.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9418
_journal_page_last               9424
_journal_paper_doi               10.1021/acs.joc.7b01406
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 N O2, Cl O4'
_chemical_formula_sum            'C20 H20 Cl N O6'
_chemical_formula_weight         405.82
_chemical_name_systematic
;
 2,6-Di(4'-methoxyphenyl)anilinium perchlorate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4384(8)
_cell_length_b                   11.3710(8)
_cell_length_c                   22.6158(19)
_cell_measurement_reflns_used    312
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2
_cell_volume                     1912.9(3)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector \f and \w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            77298
_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         27.498
_diffrn_reflns_theta_min         1.791
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0584P)^2^+0.1135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3923
_reflns_number_total             4389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01406_si_002.cif
_cod_data_source_block           p1335b
_cod_database_code               4033070
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2014-1
_shelx_res_checksum              97741
_shelx_hkl_checksum              24704