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_4127924
_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_sum            'C41 H24 Cl6 O4'
_chemical_formula_weight         793.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                73.338(15)
_cell_angle_beta                 86.579(14)
_cell_angle_gamma                84.425(14)
_cell_formula_units_Z            2
_cell_length_a                   10.195(4)
_cell_length_b                   13.289(7)
_cell_length_c                   16.613(8)
_cell_measurement_reflns_used    6476
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.718
_cell_measurement_theta_min      4.639
_cell_volume                     2144.9(18)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.987
_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  0.0952
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28434
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.747
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_platon_squeeze_details
;
;
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.083
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0835
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1343P)^2^+0.3311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4344
_reflns_number_total             7455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13884_si_003.cif
_cod_data_source_block           mo_d8v18215_0m
_cod_original_cell_volume        2144.8(18)
_cod_database_code               4127924
_shelx_estimated_absorpt_t_min   0.918
_shelx_estimated_absorpt_t_max   0.945
_shelxl_version_number           2013-4
_shelx_res_checksum              1439
_shelx_hkl_checksum              2551