Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties
Sbargoud, Kamal; Mamada, Masashi; Marrot, Jérôme; Tokito, Shizuo; Yassar, Abderrahim; Frigoli, Michel; Chem. Sci. 6 (2015) 3402–; doi:10.1039/C5SC00652J

data_1518906
_publ_section_title
;
 Diindeno[1,2-b:2&#x2032;,1&#x2032;-n]perylene: a closed shell related
 Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic
 and charge transport properties
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3402
_journal_paper_doi               10.1039/C5SC00652J
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C34 H18 O2'
_chemical_formula_weight         458.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-02-17 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.472(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.707(2)
_cell_length_b                   6.3468(10)
_cell_length_c                   13.269(3)
_cell_measurement_reflns_used    3717
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      3.06
_cell_volume                     1122.6(4)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6280
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         1.578
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.7182
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.362
_refine_ls_abs_structure_details
; 
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0650P)^2^+0.0052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                1772
_reflns_number_total             1865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00652j2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1518906--1518908.cif.'
_cod_original_cell_volume        1122.5(3)
_cod_database_code               1518906
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.990
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_shelx_hkl_checksum              61164