Pd-catalyzed homo-coupling of benzofurans: one-pot synthesis of diverse 3,3'-bisbenzofurans.
Gugulothu, Kishan; Jatoth, Ramanna; Gudipati, Ramakrishna; Rajitha, Nampally; Dandela, Rambabu; Shiva Kumar, K.; Organic & biomolecular chemistry 21 (2023) 5587–5591; doi:10.1039/d3ob00658a

data_7159441
_publ_section_title
;
 Pd-catalyzed homo-coupling of benzofurans: one-pot synthesis of diverse
 3,3'-bisbenzofurans.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5587
_journal_page_last               5591
_journal_paper_doi               10.1039/d3ob00658a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C40 H26 O4'
_chemical_formula_sum            'C40 H26 O4'
_chemical_formula_weight         570.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-02-08 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3643(4)
_cell_length_b                   7.5268(4)
_cell_length_c                   31.4217(12)
_cell_measurement_reflns_used    7932
_cell_measurement_temperature    296.71
_cell_measurement_theta_max      18.6690
_cell_measurement_theta_min      2.5720
_cell_volume                     2924.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.71
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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     -8.00  86.00   0.50    2.00    --   16.22  45.00   0.00  188
  2  \w     -6.00  28.00   0.50    2.00    --  -14.97-105.00  77.96   68
  3  \w    -37.00  22.00   0.50    2.00    --  -14.97 -94.00  30.00  118
  4  \w    -62.00  63.00   0.50    2.00    --   16.22 -16.00 -10.00  250
  5  \w    -39.00  55.00   0.50    2.00    --  -14.97  45.00 -90.00  188
  6  \w     -8.00  86.00   0.50    2.00    --   16.22  45.00-180.00  188
  7  \w    -37.00  22.00   0.50    2.00    --  -14.97 -94.00-150.00  118
  8  \w    -37.00  22.00   0.50    2.00    --  -14.97 -94.00-180.00  118
  9  \w    -57.00  41.00   0.50    2.00    --   16.22 -30.00 -90.00  196
 10  \w    -37.00  22.00   0.50    2.00    --  -14.97 -94.00 -60.00  118
 11  \w    -94.00  32.00   0.50    2.00    --  -14.97 -16.00 -10.00  252
 12  \w    -69.00 -10.00   0.50    2.00    --  -14.97 125.00 -90.00  118
 13  \w    -69.00 -10.00   0.50    2.00    --  -14.97 125.00 -60.00  118
 14  \w    -69.00 -10.00   0.50    2.00    --  -14.97 125.00   0.00  118
 15  \w    -69.00 -10.00   0.50    2.00    --  -14.97 125.00  60.00  118
 16  \w    -69.00 -10.00   0.50    2.00    --  -14.97 125.00 120.00  118
 17  \w    -65.00  64.00   0.50    2.00    --  -14.97  16.00 159.00  258
 18  \w    -34.00  95.00   0.50    2.00    --   16.22  16.00 159.00  258
 19  \w    -85.00  13.00   0.50    2.00    --  -14.97 -61.00 150.00  196
 20  \w    -88.00  16.00   0.50    2.00    --  -14.97 -77.00  30.00  208
 21  \w    -85.00  10.00   0.50    2.00    --  -14.97 -45.00-180.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068957000
_diffrn_orient_matrix_UB_12      0.0221670000
_diffrn_orient_matrix_UB_13      -0.0137902000
_diffrn_orient_matrix_UB_21      -0.0102876000
_diffrn_orient_matrix_UB_22      0.0037479000
_diffrn_orient_matrix_UB_23      0.0913715000
_diffrn_orient_matrix_UB_31      0.0560096000
_diffrn_orient_matrix_UB_32      -0.0020545000
_diffrn_orient_matrix_UB_33      0.0184787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            63678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.963
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6198
_refine_ls_number_restraints     373
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.2374
_refine_ls_R_factor_gt           0.1349
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3198
_refine_ls_wR_factor_ref         0.4051
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2598
_reflns_number_total             6198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00658a2.cif
_cod_data_source_block           exter178
_cod_depositor_comments          'Adding full bibliography for 7159441.cif.'
_cod_database_code               7159441
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H26 O4'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C40-C35
 1.4 with sigma of 0.02
 C35-C40
 1.5 with sigma of 0.02
 C19-C20 \\sim C20-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C15) = Uanis(C20) = Uanis(C19) = Uanis(C18) = Uanis(C17) =
Uanis(C35) = Uanis(C36) = Uanis(C37) = Uanis(C38) = Uanis(C39) = Uanis(C40)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C30(H30), C14(H14), C5(H5), C2(H2), C34(H34), C40(H40), C24(H24), C23(H23),
 C22(H22), C3(H3), C31(H31), C25(H25), C10(H10), C11(H11), C4(H4), C33(H33),
 C13(H13), C39(H39), C38(H38), C36(H36), C37(H37), C20(H20), C19(H19), C16(H16),
  C18(H18), C17(H17)
;
_shelx_res_checksum              33177
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.589