Direct functionalization of polycyclic aromatics via radical perfluoroalkylation.
Li, Yan; Li, Cheng; Yue, Wan; Jiang, Wei; Kopecek, Ralf; Qu, Jianqiang; Wang, Zhaohui; Organic letters 12 (2010) 2374–2377; doi:10.1021/ol1007197

data_1502982
_publ_section_title
;
 Direct functionalization of polycyclic aromatics via radical
 perfluoroalkylation.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2374
_journal_page_last               2377
_journal_paper_doi               10.1021/ol1007197
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C24 H9 F17'
_chemical_formula_sum            'C24 H9 F17'
_chemical_formula_weight         620.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.056(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0062(12)
_cell_length_b                   11.4277(13)
_cell_length_c                   10.594(2)
_cell_measurement_reflns_used    978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.12
_cell_volume                     2222.0(5)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25336
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         4.56
_exptl_absorpt_coefficient_mu    1.913
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0855
_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^)+(0.0819P)^2^+3.3808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2132
_reflns_number_gt                2888
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1007197_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502982