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_4033743
_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 unk
_chemical_formula_moiety         'C26 H12 F4'
_chemical_formula_sum            'C26 H12 F4'
_chemical_formula_weight         400.37
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6014(3)
_cell_length_b                   11.0951(4)
_cell_length_c                   21.1486(10)
_cell_measurement_reflns_used    9507
_cell_measurement_temperature    100
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1783.64(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20183
_diffrn_reflns_theta_full        27.193
_diffrn_reflns_theta_max         27.193
_diffrn_reflns_theta_min         1.926
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9294
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.0001599
_refine_ls_shift/su_mean         0.0000135
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 4.59P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1598
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1549
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2122
_reflns_number_total             2285
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0647
_oxford_refine_ls_scale          0.16558(19)
_oxford_reflns_number_all        2273
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_iucr_refine_instructions_details_constraints
;
FULL F(1,X'S,U'S) UNTIL C(26) 
RIDE C ( 1,X'S) H( 11,X'S) 
RIDE C ( 2,X'S) H( 21,X'S) 
RIDE C ( 3,X'S) H( 31,X'S) 
RIDE C ( 4,X'S) H( 41,X'S) 
RIDE C ( 6,X'S) H( 61,X'S) 
RIDE C ( 7,X'S) H( 71,X'S) 
RIDE C ( 9,X'S) H( 91,X'S) 
RIDE C ( 10,X'S) H( 101,X'S) 
RIDE C ( 12,X'S) H( 121,X'S) 
RIDE C ( 13,X'S) H( 131,X'S) 
RIDE C ( 15,X'S) H( 151,X'S) 
RIDE C ( 16,X'S) H( 161,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
END                                                                             
;
_cod_data_source_file            jo8b02870_si_005.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4033743