F-THENA: a chiral derivatizing agent for the determination of the absolute configuration of secondary aromatic alcohols with a self-validating system.
Dolsophon, Kulvadee; Soponpong, Jakapun; Kornsakulkarn, Jittra; Thongpanchang, Chawanee; Prabpai, Samran; Kongsaeree, Palangpon; Thongpanchang, Tienthong; Organic & biomolecular chemistry 14 (2016) 11002–11012; doi:10.1039/c6ob02255c

data_7155347
_publ_section_title
;
 F-THENA: a chiral derivatizing agent for the determination of the
 absolute configuration of secondary aromatic alcohols with a
 self-validating system.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11002
_journal_page_last               11012
_journal_paper_doi               10.1039/c6ob02255c
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H20 F N O3'
_chemical_formula_sum            'C20 H20 F N O3'
_chemical_formula_weight         341.37
_chemical_name_common            F-THENA
_chemical_name_systematic
'8-Fluoro-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid'
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-03 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2370(3)
_cell_length_b                   10.2370(3)
_cell_length_c                   16.6750(4)
_cell_measurement_reflns_used    4966
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.998
_cell_volume                     1747.48(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       KappaCCD2000
_computing_data_reduction
'HKL Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3860
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.243
_diffrn_reflns_theta_min         4.165
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0426P)^2^+0.2054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3519
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02255c2.cif
_cod_data_source_block           F-THENA
_cod_depositor_comments          'Adding full bibliography for 7155347.cif.'
_cod_original_cell_volume        1747.48(11)
_cod_database_code               7155347
_shelxl_version_number           2013-4
_shelx_res_checksum              11851