Bridging the Gap between Pentacene and Perfluoropentacene: Synthesis and Characterization of 2,3,9,10-Tetrafluoropentacene in the Neutral, Cationic, and Dicationic States.
Shen, Bin; Geiger, Thomas; Einholz, Ralf; Reicherter, Florian; Schundelmeier, Simon; Maichle-Mössmer, Cäcilia; Speiser, Bernd; Bettinger, Holger F.; The Journal of organic chemistry 83 (2018) 3149–3158; doi:10.1021/acs.joc.7b03241

data_4035152
_publ_section_title
;
 Bridging the Gap between Pentacene and Perfluoropentacene: Synthesis and
 Characterization of 2,3,9,10-Tetrafluoropentacene in the Neutral,
 Cationic, and Dicationic States.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3149
_journal_page_last               3158
_journal_paper_doi               10.1021/acs.joc.7b03241
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C25.5 H19 F4 O0.5'
_chemical_formula_weight         409.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 101.088(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2856(4)
_cell_length_b                   23.0002(6)
_cell_length_c                   13.9552(4)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.69
_cell_volume                     3869.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      111(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.094
_diffrn_reflns_theta_min         1.771
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+4.4643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6464
_reflns_number_total             8500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03241_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C51 H38 F8 O'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     818.81
_cod_database_code               4035152
_shelxl_version_number           2014-3
_shelx_res_checksum              99648
_shelx_hkl_checksum              61668