#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/48/4124830.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_4124830
loop_
_publ_author_name
'Gu, Xiao'
'Xu, Xiaomin'
'Li, Huiyan'
'Liu, Zhifeng'
'Miao, Qian'
_publ_section_title
;
 Synthesis, Molecular Packing, and Thin Film Transistors of
 Dibenzo[a,m]rubicenes.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16203
_journal_page_last               16208
_journal_paper_doi               10.1021/jacs.5b10687
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C50 H34 O4'
_chemical_formula_weight         698.77
_chemical_name_systematic
; 
 5,14-di(3,5-dimethoxyphenyl)dibenzo[a,m]rubicene 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0444(6)
_cell_length_b                   5.7447(3)
_cell_length_c                   25.5486(14)
_cell_measurement_reflns_used    92
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1733.92(16)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13459
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                2385
_reflns_number_total             3110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b10687_si_006.cif
_cod_data_source_block           DMP-dibenzorubicene
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4124830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.49648(10) -0.0923(2) 0.22462(5) 0.0620(4) Uani 1 1 d .
O2 O 0.66045(10) 0.5605(2) 0.15466(5) 0.0666(4) Uani 1 1 d .
C1 C 0.59486(18) -0.1188(4) 0.26489(8) 0.0798(7) Uani 1 1 d .
H1A H 0.5855 -0.2498 0.2870 0.120 Uiso 1 1 calc R
H1B H 0.6064 0.0195 0.2864 0.120 Uiso 1 1 calc R
H1C H 0.6593 -0.1440 0.2486 0.120 Uiso 1 1 calc R
C2 C 0.49424(13) 0.0855(3) 0.18902(6) 0.0430(4) Uani 1 1 d .
C3 C 0.39683(13) 0.0984(3) 0.14959(6) 0.0432(4) Uani 1 1 d .
H3A H 0.3389 -0.0093 0.1490 0.052 Uiso 1 1 calc R
C4 C 0.38616(12) 0.2703(3) 0.11148(6) 0.0394(4) Uani 1 1 d .
C5 C 0.47234(13) 0.4313(3) 0.11167(6) 0.0438(4) Uani 1 1 d .
H5A H 0.4650 0.5477 0.0859 0.053 Uiso 1 1 calc R
C6 C 0.56916(13) 0.4155(3) 0.15078(6) 0.0447(4) Uani 1 1 d .
C7 C 0.58015(13) 0.2438(3) 0.18965(6) 0.0480(4) Uani 1 1 d .
H7A H 0.6453 0.2358 0.2160 0.058 Uiso 1 1 calc R
C8 C 0.65642(17) 0.7397(3) 0.11620(8) 0.0649(5) Uani 1 1 d .
H8A H 0.7255 0.8277 0.1237 0.097 Uiso 1 1 calc R
H8B H 0.5936 0.8406 0.1176 0.097 Uiso 1 1 calc R
H8C H 0.6475 0.6721 0.0813 0.097 Uiso 1 1 calc R
C9 C 0.27941(12) 0.2846(3) 0.06983(6) 0.0384(4) Uani 1 1 d .
C10 C 0.26176(13) 0.1332(3) 0.02351(6) 0.0378(4) Uani 1 1 d .
C11 C 0.34471(14) -0.0298(3) 0.01723(6) 0.0484(4) Uani 1 1 d .
H11A H 0.4152 -0.0231 0.0398 0.058 Uiso 1 1 calc R
C12 C 0.32484(16) -0.1982(3) -0.02119(7) 0.0542(5) Uani 1 1 d .
H12A H 0.3825 -0.2995 -0.0256 0.065 Uiso 1 1 calc R
C13 C 0.21854(15) -0.2177(3) -0.05354(6) 0.0483(4) Uani 1 1 d .
H13A H 0.2029 -0.3400 -0.0777 0.058 Uiso 1 1 calc R
C14 C 0.13657(14) -0.0560(3) -0.04980(6) 0.0415(4) Uani 1 1 d .
H14A H 0.0652 -0.0716 -0.0713 0.050 Uiso 1 1 calc R
C15 C 0.15778(12) 0.1326(3) -0.01422(6) 0.0354(3) Uani 1 1 d .
C16 C 0.19340(12) 0.4255(3) 0.07666(6) 0.0371(4) Uani 1 1 d .
C17 C 0.09395(12) 0.4493(2) 0.03530(5) 0.0330(3) Uani 1 1 d .
C18 C 0.02182(12) 0.6207(2) 0.04999(5) 0.0341(3) Uani 1 1 d .
C19 C 0.07023(12) 0.6854(3) 0.10625(5) 0.0373(4) Uani 1 1 d .
C20 C 0.02778(14) 0.8077(3) 0.14485(6) 0.0469(4) Uani 1 1 d .
H20A H -0.0437 0.8750 0.1365 0.056 Uiso 1 1 calc R
C21 C 0.09197(15) 0.8296(3) 0.19582(6) 0.0521(5) Uani 1 1 d .
H21A H 0.0633 0.9137 0.2213 0.063 Uiso 1 1 calc R
C22 C 0.19713(15) 0.7294(3) 0.20950(6) 0.0479(4) Uani 1 1 d .
H22A H 0.2397 0.7496 0.2437 0.058 Uiso 1 1 calc R
C23 C 0.23978(13) 0.5988(3) 0.17256(6) 0.0411(4) Uani 1 1 d .
H23A H 0.3104 0.5283 0.1819 0.049 Uiso 1 1 calc R
C24 C 0.17632(12) 0.5737(3) 0.12140(5) 0.0362(3) Uani 1 1 d .
C25 C -0.07504(12) 0.6826(2) 0.01206(5) 0.0331(3) 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_1
_geom_angle_site_symmetry_3
C2 O1 C1 117.98(14) . .
C6 O2 C8 118.27(14) . .
O1 C2 C7 124.75(14) . .
O1 C2 C3 115.26(14) . .
C7 C2 C3 119.99(14) . .
C4 C3 C2 120.00(15) . .
C3 C4 C5 120.58(14) . .
C3 C4 C9 119.30(14) . .
C5 C4 C9 120.11(13) . .
C6 C5 C4 118.88(14) . .
O2 C6 C5 124.41(15) . .
O2 C6 C7 114.71(14) . .
C5 C6 C7 120.89(15) . .
C2 C7 C6 119.66(14) . .
C16 C9 C10 118.03(13) . .
C16 C9 C4 120.83(14) . .
C10 C9 C4 120.94(13) . .
C11 C10 C15 118.28(14) . .
C11 C10 C9 119.97(14) . .
C15 C10 C9 121.57(13) . .
C12 C11 C10 121.76(16) . .
C11 C12 C13 119.86(16) . .
C14 C13 C12 119.81(16) . .
C13 C14 C15 121.60(15) . .
C14 C15 C10 117.71(14) . .
C14 C15 C25 122.95(14) . 3_565
C10 C15 C25 119.21(13) . 3_565
C9 C16 C17 120.68(13) . .
C9 C16 C24 132.30(14) . .
C17 C16 C24 107.03(12) . .
C25 C17 C18 126.80(13) 3_565 .
C25 C17 C16 123.46(13) 3_565 .
C18 C17 C16 109.74(12) . .
C25 C18 C17 117.60(12) . .
C25 C18 C19 135.78(14) . .
C17 C18 C19 106.57(12) . .
C20 C19 C24 118.25(13) . .
C20 C19 C18 133.11(14) . .
C24 C19 C18 108.30(13) . .
C21 C20 C19 119.93(15) . .
C22 C21 C20 121.33(15) . .
C21 C22 C23 120.09(15) . .
C22 C23 C24 119.35(15) . .
C23 C24 C19 120.90(14) . .
C23 C24 C16 131.08(14) . .
C19 C24 C16 107.77(12) . .
C17 C25 C18 115.39(13) 3_565 .
C17 C25 C15 115.16(13) 3_565 3_565
C18 C25 C15 129.44(13) . 3_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3648(19) .
O1 C1 1.418(2) .
O2 C6 1.3678(19) .
O2 C8 1.417(2) .
C2 C7 1.375(2) .
C2 C3 1.392(2) .
C3 C4 1.375(2) .
C4 C5 1.389(2) .
C4 C9 1.503(2) .
C5 C6 1.383(2) .
C6 C7 1.388(2) .
C9 C16 1.353(2) .
C9 C10 1.451(2) .
C10 C11 1.401(2) .
C10 C15 1.424(2) .
C11 C12 1.366(2) .
C12 C13 1.387(2) .
C13 C14 1.372(2) .
C14 C15 1.405(2) .
C15 C25 1.464(2) 3_565
C16 C17 1.4412(19) .
C16 C24 1.472(2) .
C17 C25 1.4081(19) 3_565
C17 C18 1.411(2) .
C18 C25 1.4096(19) .
C18 C19 1.4891(19) .
C19 C20 1.387(2) .
C19 C24 1.415(2) .
C20 C21 1.385(2) .
C21 C22 1.373(2) .
C22 C23 1.381(2) .
C23 C24 1.3870(19) .
C25 C17 1.4080(19) 3_565
C25 C15 1.464(2) 3_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134954623
