Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings.
Církva, Vladimír; Jakubík, Pavel; Strašák, Tomáš; Hrbáč, Jan; Sýkora, Jan; Císařová, Ivana; Vacek, Jan; Žádný, Jaroslav; Storch, Jan; The Journal of organic chemistry 84 (2019) 1980–1993; doi:10.1021/acs.joc.8b02870

data_4033747
_publ_section_title
;
 Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at
 Terminal Rings.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1980
_journal_page_last               1993
_journal_paper_doi               10.1021/acs.joc.8b02870
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration P
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C26 H12 F4'
_chemical_formula_sum            'C26 H12 F4'
_chemical_formula_weight         400.36
_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     direct
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6059(2)
_cell_length_b                   11.0958(3)
_cell_length_c                   21.1436(7)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    121(2)
_cell_measurement_theta_max      69.8494
_cell_measurement_theta_min      3.9840
_cell_volume                     1784.38(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      121(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8609
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.088
_diffrn_reflns_theta_min         4.182
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       bar
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1150 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(9)
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0319P)^2^+1.0689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3055
_reflns_number_total             3341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02870_si_004.cif
_cod_data_source_block           cu_js_f26hel_sykora
_cod_database_code               4033747
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.774
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              85548
_shelx_hkl_checksum              97965