Expedient regioselective synthesis of all-different tetraaryl furans.
Bu, Shixuan; Wang, Haoran; Wang, Sunewang R.; Organic & biomolecular chemistry 23 (2025) 9602–9607; doi:10.1039/d5ob01484k

data_7160780
_publ_section_title
;
 Expedient regioselective synthesis of all-different tetraaryl furans.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9602
_journal_page_last               9607
_journal_paper_doi               10.1039/d5ob01484k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C34 H26 O3'
_chemical_formula_sum            'C34 H26 O3'
_chemical_formula_weight         482.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-24 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9007(2)
_cell_length_b                   10.25550(10)
_cell_length_c                   27.1733(3)
_cell_measurement_reflns_used    18320
_cell_measurement_temperature    172(1)
_cell_measurement_theta_max      73.3950
_cell_measurement_theta_min      4.0620
_cell_volume                     4988.49(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_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    -28.00  27.00   1.00    2.00    --    0.00 -37.00-150.00   55
  2  \w    -85.00 -26.00   1.00    2.00    --    0.00 -77.00-150.00   59
  3  \w     -9.00  33.00   1.00    2.00    --    0.00 -77.00-150.00   42
  4  \w    -27.00  12.00   1.00    2.00    --    0.00  37.00 120.00   39
  5  \w     43.00  69.00   1.00    2.00    --    0.00  57.00  30.00   26
  6  \w     40.00  66.00   1.00    2.00    --    0.00  37.00 120.00   26
  7  \w    -89.00  18.00   1.00    2.00    --    0.00 -57.00 120.00  107
  8  \w     69.00 164.00   1.00    3.00    --   92.10  45.00 -30.00   95
  9  \w     93.00 119.00   1.00    3.00    --   92.10 -82.00  30.00   26
 10  \w     11.00  53.00   1.00    3.00    --   92.10 -82.00-120.00   42
 11  \w     14.00  58.00   1.00    3.00    --   92.10 -82.00   0.00   44
 12  \w     66.00 182.00   1.00    3.00    --   92.10  45.00 -60.00  116
 13  \w     64.00 180.00   1.00    3.00    --   92.10  61.00  30.00  116
 14  \w      3.00 120.00   1.00    3.00    --   92.10 -61.00-150.00  117
 15  \w     11.00 128.00   1.00    3.00    --   92.10 -82.00  90.00  117
 16  \w      4.00  29.00   1.00    3.00    --   92.10 -82.00  30.00   25
 17  \w     69.00 109.00   1.00    3.00    --   92.10  30.00-180.00   40
 18  \w     76.00 128.00   1.00    3.00    --   92.10 -82.00 -60.00   52
 19  \w    130.00 156.00   1.00    3.00    --   92.10  30.00-180.00   26
 20  \w      7.00  33.00   1.00    3.00    --   92.10 -82.00 -60.00   26
 21  \w      4.00  46.00   1.00    3.00    --   92.10 -82.00-150.00   42
 22  \w     94.00 120.00   1.00    3.00    --   92.10 -82.00 120.00   26
 23  \w     71.00 128.00   1.00    3.00    --   92.10 -82.00-120.00   57
 24  \w     84.00 109.00   1.00    3.00    --   92.10 -82.00   0.00   25
 25  \w      6.00 119.00   1.00    3.00    --   92.10 -61.00  90.00  113
 26  \w     93.00 119.00   1.00    3.00    --   92.10 -82.00 -90.00   26
 27  \w     96.00 122.00   1.00    3.00    --   92.10 -82.00 150.00   26
 28  \w     61.00 122.00   1.00    3.00    --   92.10  82.00  30.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0004771000
_diffrn_orient_matrix_UB_12      -0.0245096000
_diffrn_orient_matrix_UB_13      0.0559208000
_diffrn_orient_matrix_UB_21      -0.0122436000
_diffrn_orient_matrix_UB_22      -0.1466913000
_diffrn_orient_matrix_UB_23      -0.0090899000
_diffrn_orient_matrix_UB_31      0.0852291000
_diffrn_orient_matrix_UB_32      -0.0208607000
_diffrn_orient_matrix_UB_33      -0.0016603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00094(10)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0440P)^2^+1.6588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3952
_reflns_number_total             4455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01484k2.cif
_cod_data_source_block           exp_3919_auto
_cod_depositor_comments
'Adding full bibliography for 7160780--7160781.cif.'
_cod_database_code               7160780
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.803
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C35(H35), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
  C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C34(H34)
;
_shelx_res_checksum              64069
_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 3.582
_oxdiff_exptl_absorpt_empirical_full_min 0.455