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_7160781
_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         'C35 H22 Br Cl O2'
_chemical_formula_sum            'C35 H22 Br Cl O2'
_chemical_formula_weight         589.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.222(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9069(2)
_cell_length_b                   28.0225(8)
_cell_length_c                   15.8563(4)
_cell_measurement_reflns_used    16787
_cell_measurement_temperature    172.95(11)
_cell_measurement_theta_max      73.0410
_cell_measurement_theta_min      3.1950
_cell_volume                     2620.48(13)
_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      172.95(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_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    -63.00 -37.00   1.00    2.00    --    0.00 -76.00 -51.00   26
  2  \w    -11.00  33.00   1.00    2.00    --    0.00 -76.00 -51.00   44
  3  \w      3.00 107.00   1.00    2.00    --   92.10 -76.00 -51.00  104
  4  \w     59.00 113.00   1.00    2.00    --   92.10  76.00  75.00   54
  5  \w    -25.00  15.00   1.00    2.00    --    0.00  37.00-120.00   40
  6  \w    -26.00  88.00   1.00    2.00    --    0.00  37.00  60.00  114
  7  \w    -29.00  -3.00   1.00    2.00    --    0.00  76.00  75.00   26
  8  \w    -26.00   4.00   1.00    2.00    --    0.00  57.00  90.00   30
  9  \w    -12.00  72.00   1.00    2.00    --    0.00  82.00 -90.00   84
 10  \w     19.00  89.00   1.00    2.00    --    0.00  37.00-120.00   70
 11  \w     10.00  60.00   1.00    2.00    --    0.00  57.00  90.00   50
 12  \w    -29.00  74.00   1.00    2.00    --    0.00  77.00 -30.00  103
 13  \w      3.00 125.00   1.00    2.00    --   92.10 -77.00-180.00  122
 14  \w     57.00  82.00   1.00    2.00    --   92.10  82.00 150.00   25
 15  \w     96.00 122.00   1.00    2.00    --   92.10  60.00 141.35   26
 16  \w     59.00  86.00   1.00    2.00    --   92.10  77.00  60.00   27
 17  \w     59.00 114.00   1.00    2.00    --   92.10  77.00-120.00   55
 18  \w    136.00 182.00   1.00    2.00    --   92.10  77.00-120.00   46
 19  \w     57.00  83.00   1.00    2.00    --   92.10  82.00-180.00   26
 20  \w      9.00 128.00   1.00    2.00    --   92.10 -82.00  30.00  119
 21  \w    139.00 182.00   1.00    2.00    --   92.10  82.00 130.04   43
 22  \w    144.00 182.00   1.00    2.00    --   92.10  61.00 -45.71   38
 23  \w     64.00  90.00   1.00    2.00    --   92.10  60.00 141.35   26
 24  \w     59.00  84.00   1.00    2.00    --   92.10  77.00 -30.00   25
 25  \w     59.00  85.00   1.00    2.00    --   92.10  77.00 -60.00   26
 26  \w    138.00 163.00   1.00    2.00    --   92.10  77.00 -60.00   25
 27  \w     59.00  97.00   1.00    2.00    --   92.10  77.00  90.00   38
 28  \w    103.00 129.00   1.00    2.00    --   92.10  77.00  90.00   26
 29  \w    144.00 170.00   1.00    2.00    --   92.10  77.00  90.00   26
 30  \w     57.00  83.00   1.00    2.00    --   92.10  82.00 -90.00   26
 31  \w    154.00 180.00   1.00    2.00    --   92.10  82.00 -90.00   26
 32  \w     63.00  89.00   1.00    2.00    --   92.10  66.00 -81.49   26
 33  \w     66.00 181.00   1.00    2.00    --   92.10  45.00  90.00  115
 34  \w     59.00  84.00   1.00    2.00    --   92.10  77.00 120.00   25
 35  \w     57.00  83.00   1.00    2.00    --   92.10  82.00 130.04   26
 36  \w     36.00 126.00   1.00    2.00    --   92.10 -82.00  90.00   90
 37  \w    157.00 182.00   1.00    2.00    --   92.10  60.00  45.96   25
 38  \w     64.00  98.00   1.00    2.00    --   92.10  61.00 -45.71   34
 39  \w      9.00  35.00   1.00    2.00    --   92.10 -82.00  90.00   26
 40  \w     57.00  82.00   1.00    2.00    --   92.10  82.00-120.00   25
 41  \w     57.00  82.00   1.00    2.00    --   92.10  82.00  90.00   25
 42  \w     61.00  87.00   1.00    2.00    --   92.10  73.00 -87.40   26
 43  \w     57.00  83.00   1.00    2.00    --   92.10  82.00 -60.00   26
 44  \w     67.00 118.00   1.00    2.00    --   92.10  51.00  26.63   51
 45  \w     57.00  86.00   1.00    2.00    --   92.10  82.00-150.00   29
 46  \w     64.00 117.00   1.00    2.00    --   92.10  60.00  45.96   53
 47  \w     65.00 182.00   1.00    2.00    --   92.10  57.00 171.16  117
 48  \w     57.00  83.00   1.00    2.00    --   92.10  82.00 -30.00   26
 49  \w     57.00  82.00   1.00    2.00    --   92.10  82.00  30.00   25
 50  \w     57.00  82.00   1.00    2.00    --   92.10  82.00 120.00   25
 51  \w     64.00  89.00   1.00    2.00    --   92.10  62.00-156.38   25
 52  \w    128.00 153.00   1.00    2.00    --   92.10  62.00-156.38   25
 53  \w     59.00  84.00   1.00    2.00    --   92.10  77.00  -4.76   25
 54  \w    108.00 148.00   1.00    2.00    --   92.10  77.00  -4.76   40
 55  \w     66.00 120.00   1.00    2.00    --   92.10  46.00-144.05   54
 56  \w     66.00 182.00   1.00    2.00    --   92.10  45.00-105.50  116
 57  \w     59.00  84.00   1.00    2.00    --   92.10  78.00  15.07   25
 58  \w     58.00  83.00   1.00    2.00    --   92.10  79.00-157.11   25
 59  \w     66.00 164.00   1.00    2.00    --   92.10  45.00 150.00   98
 60  \w     67.00 160.00   1.00    2.00    --   92.10  45.00 -53.91   93
 61  \w    130.00 179.00   1.00    2.00    --   92.10  77.00  30.00   49
 62  \w    117.00 179.00   1.00    2.00    --   92.10  66.00 -81.49   62
 63  \w     59.00  84.00   1.00    2.00    --   92.10  77.00  30.00   25
 64  \w     12.00 125.00   1.00    2.00    --   92.10 -82.00-120.00  113
 65  \w    129.00 182.00   1.00    2.00    --   92.10  82.00-180.00   53
 66  \w     75.00 103.00   1.00    2.00    --   92.10 -82.00 150.00   28
 67  \w     63.00 174.00   1.00    2.00    --   92.10  64.00 -22.42  111
;
_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      -0.0057171000
_diffrn_orient_matrix_UB_12      -0.0446304000
_diffrn_orient_matrix_UB_13      0.0565021000
_diffrn_orient_matrix_UB_21      0.2513738000
_diffrn_orient_matrix_UB_22      -0.0096308000
_diffrn_orient_matrix_UB_23      -0.0150709000
_diffrn_orient_matrix_UB_31      0.0711421000
_diffrn_orient_matrix_UB_32      0.0306109000
_diffrn_orient_matrix_UB_33      0.0777557000
_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  0.1383
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18956
_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    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.751
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0742
_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^)+(0.0633P)^2^+18.1784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4101
_reflns_number_total             4666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01484k2.cif
_cod_data_source_block           exp_4516_auto
_cod_depositor_comments
'Adding full bibliography for 7160780--7160781.cif.'
_cod_database_code               7160781
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.691
_shelx_estimated_absorpt_t_min   0.515
_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:
 C23(H23), C3(H3), C2(H2), C26(H26), C25(H25), C20(H20), C14(H14), C5(H5),
 C17(H17), C22(H22), C15(H15), C19(H19), C6(H6), C28(H28), C31(H31), C12(H12),
 C16(H16), C34(H34), C33(H33)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_shelx_res_checksum              3978
_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 4.952
_oxdiff_exptl_absorpt_empirical_full_min 0.383