Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes
Aijima , Takaaki; Ueda, Rina; Nakane, Takanori; Makino, Fumiaki; Ohnishi, Yusuke; Nakajima, Keiichiro; Kamino, Shinichiro; Kurisu, Genji; Namba, Keiichi; Nakata, Hiroki; Mogi, Kaiki; Sajiki, Hironao; Akai, Shuji; Sawama, Yoshinari; ChemistrySelect  (2024) –; doi:

data_3000464
_publ_section_title
;
 Versatile Biaryls and Fused Aromatics through Oxidative Coupling of
 Hydroquinones with (Hetero)Arenes
;
_journal_name_full               ChemistrySelect
_journal_year                    2024
_chemical_absolute_configuration .
_chemical_formula_moiety         'C14 H8 O4 S2'
_chemical_formula_sum            'C14 H8 O4 S2'
_chemical_formula_weight         304.34
_chemical_melting_point_gt       471
_chemical_melting_point_lt       478
_chemical_name_systematic
'Methyl 5-hydroxy-thieno[2',3':4,5]thieno[3,2-b]benzofuran-4-carboxylate'
_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             2023-09-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                95.74
_cell_angle_beta                 92.86
_cell_angle_gamma                91.59
_cell_formula_units_Z            4
_cell_length_a                   3.711
_cell_length_b                   13.550
_cell_length_c                   22.244
_cell_measurement_reflns_used    4414
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.6230175134775144
_cell_measurement_theta_min      0.08329724652173692
_cell_volume                     1110.921
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      79
_diffrn_detector                 Ceta
_diffrn_detector_type            'CMOS camera'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_measurement_device_type  'Talos Arctica'
_diffrn_measurement_method
'continuous rotation 3D electron diffration (MicroED)'
_diffrn_radiation_probe          electron
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.01969
_diffrn_reflns_av_R_equivalents  0.3344
_diffrn_reflns_av_unetI/netI     0.1969
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38425
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        0.627
_diffrn_reflns_theta_max         0.627
_diffrn_reflns_theta_min         0.069
_diffrn_source                   '300 kV electron microscope'
_diffrn_source_type              'field emission gun'
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_description       'needle like crystal'
_exptl_crystal_F_000             230
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       35258(25)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.639
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.639
_refine_ls_R_factor_all          0.2335
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4658
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1999
_reflns_number_total             3035
_reflns_threshold_expression     'I > 2\s(I)'
_journal_article_reference       https://doi.org/10.1002/slct.202400647
_cod_data_source_file            S1_polished_twin_09A_encif4.cif
_cod_data_source_block           s1_polished_twin_09a
_cod_depositor_comments
;We noticed that Miyu Mae, Hyoga Shimizu, and Mei Harada had hardly
 contributed to the article. So, their name was removed from the author
 column.

 Releasing structure 3000464 into public domain as published material.

 The article has been published. So, the data block '_journal_name_full'
 was changed from 'to be published' to the actual journal name
 'ChemistrySelect'.
;
_cod_original_cell_volume        1110.8
_cod_database_code               3000464
_cod_database_fobs_code          3000464
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.804(7)
 0.196(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Me refined with riding coordinates:
 C029(H02A,H02B,H02C), C039(H03A,H03B,H03C)
3.b Aromatic/amide H refined with riding coordinates:
 C012(H012), C016(H016), C022(H022), C032(H032), C036(H036), C037(H037),
 C038(H038), C040(H040)
3.c Tetrahedral OH refined with riding coordinates:
 O019(H019), O021(H021)
;
_shelx_res_checksum              25473
_shelx_hkl_checksum              40014
_olex2_submission_special_instructions 'No special instructions were received'