Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape.
Banerjee, Shaibal; Sinha, Saikat; Pradhan, Padmanava; Caruso, Alessio; Liebowitz, Daniel; Parrish, Damon; Rossi, Miriam; Zajc, Barbara; The Journal of organic chemistry 81 (2016) 3983–3993; doi:10.1021/acs.joc.5b02580

data_4036536
_publ_section_title
;
 Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via
 Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of
 Fluorine Atom Substitution on Molecular Shape.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3983
_journal_page_last               3993
_journal_paper_doi               10.1021/acs.joc.5b02580
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C22 H13 F'
_chemical_formula_weight         296.32
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_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
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_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0445(17)
_cell_length_b                   7.3901(10)
_cell_length_c                   31.140(4)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.27
_cell_measurement_theta_min      2.62
_cell_volume                     2771.8(6)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28210
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
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_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
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_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.276
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_refine_ls_extinction_coef       0.0052(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2690
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_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                1539
_reflns_number_total             2690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02580_si_007.cif
_cod_data_source_block           pbca
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 
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_cod_original_cell_volume        2771.8(7)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4036536