Solvent Controlled Racemic Resolution of C3-Symmetric Trihydroxytribenzotriquinacenes.
Wagner, Philippe; Rominger, Frank; Oeser, Thomas; Mastalerz, Michael; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03410

data_4037902
_publ_section_title
;
 Solvent Controlled Racemic Resolution of C3-Symmetric
 Trihydroxytribenzotriquinacenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03410
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C33 H34 Cl3 I3 O3'
_chemical_formula_weight         965.65
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   11.2774(5)
_cell_length_b                   11.2774(5)
_cell_length_c                   24.1597(16)
_cell_measurement_reflns_used    6956
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.53
_cell_volume                     2661.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.099
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  0.9144
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_description       needle
_exptl_crystal_F_000             1398
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
; 
 Flack x determined using 1570 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0224
_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^)+(0.0177P)^2^+0.6141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0472
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3339
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03410_si_002.cif
_cod_data_source_block           phw26
_cod_original_cell_volume        2661.0(3)
_cod_database_code               4037902
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.519
_shelx_estimated_absorpt_t_max   0.898
_shelx_res_checksum              98698
_shelx_hkl_checksum              69401