Synthesis, and optical and electrochemical properties of 1,1′,3,3′-tetraaryl-4,4′-bibenzo[c]thiophene derivatives with the same or different aryl substituents on the thiophene rings
Hara, Yasuto; Kozuka, Kumpei; Imato, Keiichi; Akiyama, Seiji; Ishida, Mio; Ooyama, Yousuke; New Journal of Chemistry 48 (2024) 9890–9898; doi:10.1039/D4NJ01350F

data_7063203
_publ_section_title
;
 Synthesis, and optical and electrochemical properties of
 1,1&#x2032;,3,3&#x2032;-tetraaryl-4,4&#x2032;-bibenzo[c]thiophene
 derivatives with the same or different aryl substituents on the thiophene
 rings
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9890
_journal_page_last               9898
_journal_paper_doi               10.1039/D4NJ01350F
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C56 H58 S2, C H2 Cl2'
_chemical_formula_sum            'C57 H60 Cl2 S2'
_chemical_formula_weight         880.07
_chemical_melting_point          530.15
_chemical_name_systematic        1,1',3,3'-PhtBu-4,4?-BBT
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-03-06 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                75.521(2)
_cell_angle_beta                 80.754(2)
_cell_angle_gamma                84.376(2)
_cell_formula_units_Z            4
_cell_length_a                   14.4868(3)
_cell_length_b                   15.5221(5)
_cell_length_c                   22.5994(6)
_cell_measurement_reflns_used    22621
_cell_measurement_temperature    100.04(11)
_cell_measurement_theta_max      32.2620
_cell_measurement_theta_min      2.0250
_cell_volume                     4847.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.04(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     12.00  65.00   0.50    5.00    --    7.00  30.00-159.00  106
  2  \w    -65.00   3.00   0.50    5.00    --    7.00 -30.00  40.00  136
  3  \w    -77.00   5.00   0.50    5.00    --   -5.75 -57.00 -90.00  164
  4  \w    -72.00 -40.00   0.50    5.00    --   -5.75 -38.00-150.00   64
  5  \w    -77.00 -45.00   0.50    5.00    --   -5.75 -38.00-180.00   64
  6  \w    -58.00   6.00   0.50    5.00    --   -5.75 -57.00  30.00  128
  7  \w    -77.00  15.00   0.50    5.00    --   -5.75 -77.00 120.00  184
  8  \w     -4.00  36.00   0.50    5.00    --    7.00 -99.00  60.00   80
  9  \w    -12.00  17.00   0.50    5.00    --    7.00 -99.00   0.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0005531000
_diffrn_orient_matrix_UB_12      0.0424476000
_diffrn_orient_matrix_UB_13      0.0065260000
_diffrn_orient_matrix_UB_21      -0.0439158000
_diffrn_orient_matrix_UB_22      0.0117939000
_diffrn_orient_matrix_UB_23      -0.0108397000
_diffrn_orient_matrix_UB_31      -0.0232579000
_diffrn_orient_matrix_UB_32      -0.0171661000
_diffrn_orient_matrix_UB_33      0.0302007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            84132
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.816
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.27a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol, Dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.871
_refine_diff_density_min         -1.329
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1181
_refine_ls_number_reflns         23124
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+4.7728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16714
_reflns_number_total             23124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01350f2.cif
_cod_data_source_block           exp_2949
_cod_depositor_comments          'Adding full bibliography for 7063203.cif.'
_cod_database_code               7063203
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C56H58S2
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C1A-Cl1A \\sim C1A-Cl2A \\sim C1B-Cl1B \\sim C1B-Cl2B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1B \\sim Cl1B \\sim Cl2B \\sim C1A \\sim Cl1A \\sim Cl2A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C53B)=Sof(C55B)=Sof(H55D)=Sof(H55E)=Sof(H55F)=Sof(C56B)=Sof(H56D)=
 Sof(H56E)=Sof(H56F)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(1)
 Sof(C53A)=Sof(C55A)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56A)=Sof(H56A)=
 Sof(H56B)=Sof(H56C)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=1-FVAR(2)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB), C114(H11J,H11K)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C20(H20),
 C21(H21), C22(H22), C23(H23), C30(H30), C31(H31), C32(H32), C37(H37), C38(H38),
  C39(H39), C40(H40), C48(H48), C49(H49), C50(H50), C51(H51), C62(H62),
 C63(H63), C64(H64), C65(H65), C69(H69), C70(H70), C71(H71), C76(H76), C77(H77),
  C78(H78), C79(H79), C86(H86), C87(H87), C88(H88), C94(H94), C95(H95),
 C96(H96), C97(H97), C104(H104), C105(H105), C106(H106), C107(H107)
5.c Idealised Me refined as rotating group:
 C55A(H55A,H55B,H55C), C56A(H56A,H56B,H56C), C55B(H55D,H55E,H55F), C56B(H56D,
 H56E,H56F), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C), C45(H45A,H45B,H45C), C54(H54A,H54B,H54C), C54(H54D,H54E,H54F),
 C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C82(H82A,H82B,
 H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C100(H10A,H10B,H10C),
 C101(H10D,H10E,H10F), C102(H10G,H10H,H10I), C110(H11A,H11B,H11C), C111(H11D,
 H11E,H11F), C112(H11G,H11H,H11I)
;
_shelx_res_checksum              21939
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.831