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_4036537
_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            'C18 H12'
_chemical_formula_weight         228.28
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.64(4)
_cell_length_b                   6.163(12)
_cell_length_c                   8.231(15)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      29.72
_cell_measurement_theta_min      3.43
_cell_volume                     1138(4)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
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_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6906
_diffrn_reflns_theta_full        28.68
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triangular
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0544
_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^)+(0.1277P)^2^+0.6470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.2090
_reflns_number_gt                945
_reflns_number_total             1460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02580_si_004.cif
_cod_data_source_block           chry3_0m
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4036537