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
Watanabe, Hikaru; Sato, Takuma; Sumita, Michiki; Shiroyama, Mei; Sugawara, Daichi; Tokuyama, Tomoki; Okuda, Yasuhiro; Wakamatsu, Kan; Akashi, Haruo; Orita, Akihiro; Acta Crystallographica Section E Crystallographic Communications 79 (2023) 757–761; doi:10.1107/S2056989023006187

data_2022829
_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
;
(<i>E</i>,<i>E</i>)-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 <i>et al.</i>, 2009)
;
_computing_publication_material
;
Olex2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (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       '\w 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 <i>x</i> obtained using 1343 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i> (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/[\s^2^(Fo^2^)+(0.0399P)^2^+0.5407P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            pk2689sup1.cif
_cod_data_source_block           I
_cod_database_code               2022829
_shelx_hkl_checksum              85871
_shelx_res_checksum              26370
_cod_database_fobs_code 2022829