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_4127921
_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         'C67 H34 Cl10 O6'
_chemical_formula_sum            'C67 H34 Cl10 O6'
_chemical_formula_weight         1289.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                107.665(6)
_cell_angle_beta                 96.056(7)
_cell_angle_gamma                96.264(7)
_cell_formula_units_Z            2
_cell_length_a                   11.5455(12)
_cell_length_b                   18.2487(17)
_cell_length_c                   22.786(2)
_cell_measurement_reflns_used    8298
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.29
_cell_measurement_theta_min      3.280
_cell_volume                     4498.2(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            53216
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.343
_diffrn_reflns_theta_min         3.280
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.042
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1340 before and 0.0841 after correction. The Ratio of minimum to maximum transmission is 0.6072. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.952
_exptl_crystal_description       plate
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     750
_refine_ls_number_reflns         16979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.2021
_refine_ls_R_factor_gt           0.1280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+30.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3000
_refine_ls_wR_factor_ref         0.3547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6511
_reflns_number_total             16979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13884_si_005.cif
_cod_data_source_block           mjl18055_0m
_cod_original_cell_volume        4498.1(8)
_cod_database_code               4127921
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.749
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C13(H13), C16(H16), C17(H17), C19(H19), C23(H23),
 C26(H26), C30(H30), C33(H33), C38(H38), C39(H39), C40(H40), C45(H45), C46(H46),
  C47(H47), C51(H51), C52(H52), C53(H53), C57(H57), C58(H58), C59(H59),
 C63(H63), C64(H64), C65(H65)
2.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C67(H67A,H67B,H67C)
;
_shelx_res_checksum              3283
_shelx_hkl_checksum              92070
_shelx_fab_checksum              60129
_olex2_submission_special_instructions 'No special instructions were received'