#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/89/1518906.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1518906
loop_
_publ_author_name
'Sbargoud, Kamal'
'Mamada, Masashi'
'Marrot, Jérôme'
'Tokito, Shizuo'
'Yassar, Abderrahim'
'Frigoli, Michel'
_publ_section_title
;
 Diindeno[1,2-b:2′,1′-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       'φ and ω 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/[σ²(Fo²)+(0.0650P)²+0.0052P] where P=(Fo²+2Fc²)/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 > 2σ(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
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_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'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.59289(12) 0.6418(4) 0.72417(15) 0.0559(6) Uani 1 1 d . .
C2 C 0.67221(17) 0.5586(4) 0.72266(18) 0.0354(6) Uani 1 1 d . .
C3 C 0.68576(17) 0.3610(4) 0.66623(17) 0.0359(6) Uani 1 1 d . .
C4 C 0.6147(2) 0.2287(5) 0.6078(2) 0.0464(7) Uani 1 1 d . .
H4 H 0.5466 0.2575 0.5973 0.056 Uiso 1 1 calc R U
C5 C 0.6486(2) 0.0504(5) 0.5651(2) 0.0503(7) Uani 1 1 d . .
H5 H 0.6024 -0.0409 0.5248 0.060 Uiso 1 1 calc R U
C6 C 0.7500(2) 0.0075(4) 0.58167(19) 0.0471(7) Uani 1 1 d . .
H6 H 0.7709 -0.1115 0.5516 0.056 Uiso 1 1 calc R U
C7 C 0.82136(19) 0.1388(4) 0.64240(18) 0.0399(6) Uani 1 1 d . .
H7 H 0.8894 0.1081 0.6543 0.048 Uiso 1 1 calc R U
C8 C 0.78801(17) 0.3159(4) 0.68443(16) 0.0331(6) Uani 1 1 d . .
C9 C 0.84289(16) 0.4803(4) 0.75420(16) 0.0322(5) Uani 1 1 d . .
C10 C 0.94599(17) 0.4980(4) 0.79823(18) 0.0400(6) Uani 1 1 d . .
H10 H 0.9913 0.4042 0.7804 0.048 Uiso 1 1 calc R U
C11 C 0.97821(16) 0.6556(5) 0.86776(18) 0.0385(6) Uani 1 1 d . .
H11 H 1.0463 0.6649 0.8987 0.046 Uiso 1 1 calc R U
C12 C 0.91216(15) 0.8063(4) 0.89496(17) 0.0311(5) Uani 1 1 d . .
C13 C 0.94636(16) 0.9679(4) 0.96953(16) 0.0321(6) Uani 1 1 d . .
C14 C 0.88085(17) 1.1197(4) 0.98558(18) 0.0370(6) Uani 1 1 d . .
H14 H 0.9035 1.2263 1.0334 0.044 Uiso 1 1 calc R U
C15 C 0.77922(17) 1.1172(4) 0.93073(19) 0.0375(6) Uani 1 1 d . .
H15 H 0.7366 1.2251 0.9409 0.045 Uiso 1 1 calc R U
C16 C 0.74311(16) 0.9592(4) 0.86329(17) 0.0335(6) Uani 1 1 d . .
H16 H 0.6756 0.9573 0.8293 0.040 Uiso 1 1 calc R U
C17 C 0.80758(15) 0.7976(4) 0.84453(16) 0.0291(5) Uani 1 1 d . .
C18 C 0.77598(16) 0.6258(4) 0.77719(17) 0.0313(5) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
O1 C2 C3 126.2(2) .
O1 C2 C18 128.4(2) .
C3 C2 C18 105.40(19) .
C4 C3 C8 121.4(2) .
C4 C3 C2 129.7(2) .
C8 C3 C2 108.8(2) .
C3 C4 C5 117.7(3) .
C3 C4 H4 121.1 .
C5 C4 H4 121.1 .
C6 C5 C4 120.9(3) .
C6 C5 H5 119.6 .
C4 C5 H5 119.6 .
C5 C6 C7 121.3(3) .
C5 C6 H6 119.3 .
C7 C6 H6 119.3 .
C8 C7 C6 117.9(2) .
C8 C7 H7 121.0 .
C6 C7 H7 121.0 .
C7 C8 C3 120.8(2) .
C7 C8 C9 131.3(2) .
C3 C8 C9 107.9(2) .
C18 C9 C10 120.7(2) .
C18 C9 C8 110.00(19) .
C10 C9 C8 129.3(2) .
C11 C10 C9 118.5(2) .
C11 C10 H10 120.8 .
C9 C10 H10 120.8 .
C10 C11 C12 122.8(2) .
C10 C11 H11 118.6 .
C12 C11 H11 118.6 .
C11 C12 C13 122.3(2) .
C11 C12 C17 118.8(2) .
C13 C12 C17 118.8(2) .
C14 C13 C12 119.5(2) .
C14 C13 C13 120.77(18) 2_757
C12 C13 C13 119.68(17) 2_757
C13 C14 C15 121.1(2) .
C13 C14 H14 119.5 .
C15 C14 H14 119.5 .
C16 C15 C14 120.7(2) .
C16 C15 H15 119.6 .
C14 C15 H15 119.6 .
C15 C16 C17 120.3(2) .
C15 C16 H16 119.8 .
C17 C16 H16 119.8 .
C18 C17 C16 124.03(19) .
C18 C17 C12 116.77(19) .
C16 C17 C12 119.2(2) .
C9 C18 C17 122.21(19) .
C9 C18 C2 107.9(2) .
C17 C18 C2 129.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.213(3) .
C2 C3 1.494(3) .
C2 C18 1.500(3) .
C3 C4 1.379(4) .
C3 C8 1.395(3) .
C4 C5 1.393(4) .
C4 H4 0.9300 .
C5 C6 1.383(4) .
C5 H5 0.9300 .
C6 C7 1.390(4) .
C6 H6 0.9300 .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.479(3) .
C9 C18 1.384(3) .
C9 C10 1.402(3) .
C10 C11 1.363(4) .
C10 H10 0.9300 .
C11 C12 1.420(3) .
C11 H11 0.9300 .
C12 C13 1.426(3) .
C12 C17 1.435(3) .
C13 C14 1.367(3) .
C13 C13 1.504(4) 2_757
C14 C15 1.413(3) .
C14 H14 0.9300 .
C15 C16 1.358(4) .
C15 H15 0.9300 .
C16 C17 1.413(3) .
C16 H16 0.9300 .
C17 C18 1.413(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044783
