Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral Derivatizing Agent for α-Chiral Primary Amines and Secondary Alcohols To Determine the Absolute Configuration.
Kriegelstein, Michal; Profous, David; Lyčka, Antonín; Trávníček, Zdeněk; Přibylka, Adam; Volná, Tereza; Benická, Sandra; Cankař, Petr; The Journal of organic chemistry 84 (2019) 11911–11921; doi:10.1021/acs.joc.9b01770

data_4034459
_publ_section_title
;
 Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral
 Derivatizing Agent for \a-Chiral Primary Amines and Secondary Alcohols To
 Determine the Absolute Configuration.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11911
_journal_page_last               11921
_journal_paper_doi               10.1021/acs.joc.9b01770
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H18 F3 N3 O'
_chemical_formula_weight         409.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                117.806(3)
_cell_angle_beta                 90.313(3)
_cell_angle_gamma                91.209(3)
_cell_formula_units_Z            7
_cell_length_a                   11.1195(6)
_cell_length_b                   18.9600(9)
_cell_length_c                   19.2929(10)
_cell_measurement_reflns_used    7111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.17
_cell_volume                     3596.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_av_unetI/netI     0.1630
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60411
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.450
_diffrn_reflns_theta_max         24.450
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.986
_exptl_transmission_factor_min   0.982
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 4637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1926
_refine_ls_number_reflns         23612
_refine_ls_number_restraints     1731
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                14233
_reflns_number_total             23612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01770_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034459
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              67351
_shelx_hkl_checksum              12029