#------------------------------------------------------------------------------
#$Date: 2023-07-29 05:03:16 +0300 (Sat, 29 Jul 2023) $
#$Revision: 285385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022829.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022829
loop_
_publ_author_name
'Watanabe, Hikaru'
'Sato, Takuma'
'Sumita, Michiki'
'Shiroyama, Mei'
'Sugawara, Daichi'
'Tokuyama, Tomoki'
'Okuda, Yasuhiro'
'Wakamatsu, Kan'
'Akashi, Haruo'
'Orita, Akihiro'
_publ_section_title
;
 Synthesis, optical properties and crystal structure of
 (E,E)-1,3-(3,4:9,10-dibenzododeca-1,11-diene-5,7-diyne-1,12-diyl)benzene
;
_journal_coeditor_code           PK2689
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              757
_journal_page_last               761
_journal_paper_doi               10.1107/S2056989023006187
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C26 H16'
_chemical_formula_moiety         'C26 H16'
_chemical_formula_sum            'C26 H16'
_chemical_formula_weight         328.39
_chemical_name_systematic
;
(E,E)-1,3-(3,4:9,10-Dibenzododeca-1,11-diene-5,7-diyne-1,12-\
diyl)benzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6034(2)
_cell_length_b                   15.1542(7)
_cell_length_c                   24.1754(9)
_cell_measurement_reflns_used    10472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.5810
_cell_measurement_theta_min      2.1310
_cell_volume                     1686.50(12)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.589
_diffrn_reflns_theta_min         2.688
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.208
_refine_ls_abs_structure_details
;
Flack x obtained using 1343 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al. (2013)
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0578
_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)+(0.0399P)²+0.5407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                4184
_reflns_number_total             5357
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2689sup1.cif
_cod_data_source_block           I
_cod_database_code               2022829
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2502(5) 0.45575(15) 0.56944(9) 0.0216(5) Uani d 1 . .
C C2 0.4402(5) 0.47355(14) 0.61508(9) 0.0222(5) Uani d 1 . .
C C3 0.5925(5) 0.49842(14) 0.65244(9) 0.0227(5) Uani d 1 . .
C C4 0.7514(5) 0.53835(14) 0.69355(9) 0.0222(5) Uani d 1 . .
C C5 0.8704(5) 0.58321(15) 0.72752(9) 0.0209(4) Uani d 1 . .
C C6 0.9800(5) 0.64594(14) 0.76707(8) 0.0204(4) Uani d 1 . .
C C7 1.1873(5) 0.62079(15) 0.80626(9) 0.0245(5) Uani d 1 . .
H H7 1.262529 0.563841 0.805862 0.029 Uiso calc 1 . .
C C8 1.2806(6) 0.68078(16) 0.84569(9) 0.0274(5) Uani d 1 . .
H H8 1.417729 0.664064 0.871925 0.033 Uiso calc 1 . .
C C9 1.1693(5) 0.76560(16) 0.84596(9) 0.0259(5) Uani d 1 . .
H H9 1.230444 0.805469 0.872792 0.031 Uiso calc 1 . .
C C10 0.9683(5) 0.79169(15) 0.80678(9) 0.0234(5) Uani d 1 . .
H H10 0.898169 0.849244 0.807273 0.028 Uiso calc 1 . .
C C11 0.8687(5) 0.73307(14) 0.76650(8) 0.0202(4) Uani d 1 . .
C C12 0.6595(5) 0.75690(15) 0.72402(9) 0.0242(5) Uani d 1 . .
H H12 0.618597 0.711742 0.699159 0.029 Uiso calc 1 . .
C C13 0.5176(5) 0.83044(15) 0.71427(9) 0.0248(5) Uani d 1 . .
H H13 0.550528 0.878785 0.737125 0.030 Uiso calc 1 . .
C C14 0.3080(5) 0.83928(15) 0.66845(9) 0.0219(5) Uani d 1 . .
C C15 0.1742(5) 0.91902(15) 0.65530(9) 0.0217(5) Uani d 1 . .
H H15 0.218318 0.969579 0.675416 0.026 Uiso calc 1 . .
C C16 -0.0247(6) 0.92324(15) 0.61229(9) 0.0262(5) Uani d 1 . .
H H16 -0.114100 0.976703 0.604104 0.031 Uiso calc 1 . .
C C17 -0.0926(5) 0.84895(15) 0.58126(9) 0.0235(5) Uani d 1 . .
H H17 -0.226582 0.852844 0.552574 0.028 Uiso calc 1 . .
C C18 0.0403(5) 0.76861(15) 0.59313(8) 0.0215(5) Uani d 1 . .
C C19 0.2331(6) 0.76584(16) 0.63734(10) 0.0306(6) Uani d 1 . .
H H19 0.316351 0.711884 0.646541 0.037 Uiso calc 1 . .
C C20 -0.0222(5) 0.68716(16) 0.56204(9) 0.0254(5) Uani d 1 . .
H H20 -0.174216 0.687321 0.536702 0.030 Uiso calc 1 . .
C C21 0.1283(6) 0.61437(16) 0.56873(9) 0.0290(5) Uani d 1 . .
H H21 0.285437 0.620009 0.592654 0.035 Uiso calc 1 . .
C C22 0.0935(5) 0.52624(15) 0.54539(9) 0.0228(5) Uani d 1 . .
C C23 -0.0897(6) 0.50780(16) 0.50078(9) 0.0261(5) Uani d 1 . .
H H23 -0.194796 0.553344 0.484524 0.031 Uiso calc 1 . .
C C24 -0.1173(6) 0.42325(17) 0.48049(10) 0.0291(5) Uani d 1 . .
H H24 -0.238731 0.412385 0.450511 0.035 Uiso calc 1 . .
C C25 0.0346(6) 0.35453(16) 0.50444(10) 0.0311(6) Uani d 1 . .
H H25 0.013435 0.297496 0.490833 0.037 Uiso calc 1 . .
C C26 0.2182(6) 0.37044(16) 0.54866(10) 0.0270(5) Uani d 1 . .
H H26 0.320639 0.324050 0.564593 0.032 Uiso calc 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 C1 C2 . . 119.0(2) ?
C26 C1 C2 . . 121.1(2) ?
C26 C1 C22 . . 119.9(2) ?
C3 C2 C1 . . 172.6(2) ?
C2 C3 C4 . . 172.0(2) ?
C5 C4 C3 . . 171.3(2) ?
C4 C5 C6 . . 171.8(2) ?
C7 C6 C5 . . 120.6(2) ?
C7 C6 C11 . . 120.5(2) ?
C11 C6 C5 . . 118.9(2) ?
C6 C7 H7 . . 120.0 ?
C8 C7 C6 . . 119.9(2) ?
C8 C7 H7 . . 120.0 ?
C7 C8 H8 . . 120.1 ?
C9 C8 C7 . . 119.9(2) ?
C9 C8 H8 . . 120.1 ?
C8 C9 H9 . . 119.7 ?
C10 C9 C8 . . 120.7(2) ?
C10 C9 H9 . . 119.7 ?
C9 C10 H10 . . 119.5 ?
C9 C10 C11 . . 121.1(2) ?
C11 C10 H10 . . 119.5 ?
C6 C11 C12 . . 118.6(2) ?
C10 C11 C6 . . 117.9(2) ?
C10 C11 C12 . . 123.5(2) ?
C11 C12 H12 . . 114.1 ?
C13 C12 C11 . . 131.9(2) ?
C13 C12 H12 . . 114.1 ?
C12 C13 H13 . . 118.8 ?
C12 C13 C14 . . 122.5(2) ?
C14 C13 H13 . . 118.8 ?
C15 C14 C13 . . 122.6(2) ?
C19 C14 C13 . . 119.8(2) ?
C19 C14 C15 . . 117.5(2) ?
C14 C15 H15 . . 119.9 ?
C16 C15 C14 . . 120.2(2) ?
C16 C15 H15 . . 119.9 ?
C15 C16 H16 . . 119.5 ?
C15 C16 C17 . . 121.1(2) ?
C17 C16 H16 . . 119.5 ?
C16 C17 H17 . . 120.0 ?
C16 C17 C18 . . 119.9(2) ?
C18 C17 H17 . . 120.0 ?
C17 C18 C20 . . 122.8(2) ?
C19 C18 C17 . . 117.7(2) ?
C19 C18 C20 . . 119.5(2) ?
C14 C19 C18 . . 123.5(2) ?
C14 C19 H19 . . 118.3 ?
C18 C19 H19 . . 118.3 ?
C18 C20 H20 . . 118.7 ?
C21 C20 C18 . . 122.5(2) ?
C21 C20 H20 . . 118.7 ?
C20 C21 H21 . . 114.2 ?
C20 C21 C22 . . 131.6(2) ?
C22 C21 H21 . . 114.2 ?
C1 C22 C21 . . 118.5(2) ?
C23 C22 C1 . . 118.3(2) ?
C23 C22 C21 . . 123.2(2) ?
C22 C23 H23 . . 119.5 ?
C24 C23 C22 . . 121.1(2) ?
C24 C23 H23 . . 119.5 ?
C23 C24 H24 . . 119.8 ?
C23 C24 C25 . . 120.3(2) ?
C25 C24 H24 . . 119.8 ?
C24 C25 H25 . . 119.9 ?
C24 C25 C26 . . 120.1(2) ?
C26 C25 H25 . . 119.9 ?
C1 C26 H26 . . 119.9 ?
C25 C26 C1 . . 120.3(2) ?
C25 C26 H26 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.434(3) ?
C1 C22 . 1.414(3) ?
C1 C26 . 1.395(3) ?
C2 C3 . 1.204(3) ?
C3 C4 . 1.374(3) ?
C4 C5 . 1.199(3) ?
C5 C6 . 1.439(3) ?
C6 C7 . 1.398(3) ?
C6 C11 . 1.416(3) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.386(3) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.384(3) ?
C9 H9 . 0.9300 ?
C9 C10 . 1.382(3) ?
C10 H10 . 0.9300 ?
C10 C11 . 1.396(3) ?
C11 C12 . 1.454(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.313(3) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.475(3) ?
C14 C15 . 1.393(3) ?
C14 C19 . 1.387(3) ?
C15 H15 . 0.9300 ?
C15 C16 . 1.387(3) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.389(3) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.392(3) ?
C18 C19 . 1.390(3) ?
C18 C20 . 1.474(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C20 C21 . 1.313(3) ?
C21 H21 . 0.9300 ?
C21 C22 . 1.459(3) ?
C22 C23 . 1.397(3) ?
C23 H23 . 0.9300 ?
C23 C24 . 1.378(3) ?
C24 H24 . 0.9300 ?
C24 C25 . 1.382(4) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.384(3) ?
C26 H26 . 0.9300 ?

_cod_database_fobs_code 2022829
