Synthesis and Characterization of Oxygen-Embedded Quinoidal Pentacene and Nonacene.
Wang, Yanpei; Qiu, Shuhai; Xie, Sheng; Zhou, Long; Hong, Youhua; Chang, Jingjing; Wu, Jishan; Zeng, Zebing; Journal of the American Chemical Society 141 (2019) 2169–2176; doi:10.1021/jacs.8b13884

data_4127923
_publ_section_title
;
 Synthesis and Characterization of Oxygen-Embedded Quinoidal Pentacene and
 Nonacene.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2169
_journal_page_last               2176
_journal_paper_doi               10.1021/jacs.8b13884
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C50 H32 Cl8 O5'
_chemical_formula_sum            'C50 H32 Cl8 O5'
_chemical_formula_weight         996.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.529(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.2970(13)
_cell_length_b                   7.8094(4)
_cell_length_c                   23.9522(12)
_cell_measurement_reflns_used    1378
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.241
_cell_measurement_theta_min      3.679
_cell_volume                     4494.5(4)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45841
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.679
_exptl_absorpt_coefficient_mu    4.980
_exptl_absorpt_correction_T_max  0.582
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         8241
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0500P)^2^+6.4530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7267
_reflns_number_total             8241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13884_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4127923
_shelx_estimated_absorpt_t_min   0.263
_shelx_estimated_absorpt_t_max   0.582
_shelxl_version_number           2014/6
_shelx_res_checksum              98298
_shelx_hkl_checksum              50758