Synthesis of 1,1′-diaryl-4,4′-bibenzo[c]thiophene derivatives with aryl substituents on the thiophene rings by Stille or Suzuki coupling reaction
Higashino, Taiki; Hara, Yasuto; Imato, Keiichi; Akiyama, Seiji; Ishida, Mio; Ooyama, Yousuke; New Journal of Chemistry 47 (2023) 9555–9559; doi:10.1039/D3NJ01299A

data_7062459
_publ_section_title
;
 Synthesis of 1,1&#x2032;-diaryl-4,4&#x2032;-bibenzo[c]thiophene
 derivatives with aryl substituents on the thiophene rings by Stille or
 Suzuki coupling reaction
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9555
_journal_page_last               9559
_journal_paper_doi               10.1039/D3NJ01299A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C36 H34 S2'
_chemical_formula_sum            'C36 H34 S2'
_chemical_formula_weight         530.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.625(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3004(2)
_cell_length_b                   11.6368(3)
_cell_length_c                   47.0635(14)
_cell_measurement_reflns_used    14483
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.3590
_cell_measurement_theta_min      1.9600
_cell_volume                     5635.3(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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_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 1.000
_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    -17.00  31.00   0.50   15.00    --   -7.26 -99.00  60.00   96
  2  \w    -30.00  45.00   0.50   15.00    --   -7.26  57.00 120.00  150
  3  \w    -26.00  65.00   0.50   15.00    --   -7.26  57.00   0.00  182
  4  \w    -17.00  31.00   0.50   15.00    --   -7.26 -99.00-120.00   96
  5  \w    -21.00  74.00   0.50   15.00    --   -7.26  19.00-120.00  190
;
_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      -0.0089736000
_diffrn_orient_matrix_UB_12      0.0603901000
_diffrn_orient_matrix_UB_13      -0.0006641000
_diffrn_orient_matrix_UB_21      -0.0077618000
_diffrn_orient_matrix_UB_22      -0.0032045000
_diffrn_orient_matrix_UB_23      -0.0150333000
_diffrn_orient_matrix_UB_31      -0.0679085000
_diffrn_orient_matrix_UB_32      -0.0076297000
_diffrn_orient_matrix_UB_33      0.0010958000
_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  0.0726
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            51532
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.803
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71942
_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    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         10317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+9.1216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7324
_reflns_number_total             10317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01299a2.cif
_cod_data_source_block           exp_1962
_cod_depositor_comments          'Adding full bibliography for 7062459.cif.'
_cod_original_cell_volume        5635.3(3)
_cod_database_code               7062459
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C36H34S2
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C19(H19), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C31(H31), C32(H32),
  C37(H37), C40(H40), C41(H41), C42(H42), C46(H46), C47(H47), C49(H49),
 C50(H50), C55(H55), C58(H58), C59(H59), C60(H60), C64(H64), C65(H65), C67(H67),
  C68(H68)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C),
 C72(H72A,H72B,H72C)
;
_shelx_res_checksum              97470
_shelx_hkl_checksum              53753
_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 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.756