Point-to-Axial Chirality Transmission: A Highly Sensitive Triaryl Chirality Probe for Stereochemical Assignments of Amines
Mądry, Tomasz; Czapik, Agnieszka; Kwit, Marcin; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c00734

data_4038682
_publ_section_title
;
 Point-to-Axial Chirality Transmission: A Highly Sensitive Triaryl
 Chirality Probe for Stereochemical Assignments of Amines
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00734
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C36 H40 N2'
_chemical_formula_sum            'C36 H40 N2'
_chemical_formula_weight         500.70
_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     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8232(3)
_cell_length_b                   11.5685(5)
_cell_length_c                   24.8431(11)
_cell_measurement_reflns_used    5775
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      74.8500
_cell_measurement_theta_min      4.2060
_cell_volume                     2823.16(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16592
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.558
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0922
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1660P)^2^+1.4554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2667
_refine_ls_wR_factor_ref         0.2718
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4533
_reflns_number_total             4962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00734_si_003.cif
_cod_data_source_block           6c
_cod_database_code               4038682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.784
_shelx_estimated_absorpt_t_max   0.918
_shelx_res_checksum              49287