Oxidative annulations triggered by a simple Lewis acid: facile synthesis of benzofurans
Sreenivasulu, Chinnabattigalla; Gopi Krishna Reddy, A.; Satyanarayana, G.; Organic Chemistry Frontiers 4 (2017) 972–; doi:10.1039/C6QO00531D

data_1553558
_publ_section_title
;
 Oxidative annulations triggered by a simple Lewis acid: facile synthesis
 of benzofurans
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              972
_journal_paper_doi               10.1039/C6QO00531D
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_compound_source        'Synthesized compound'
_chemical_formula_moiety         'C20 H14 O'
_chemical_formula_sum            'C20 H14 O'
_chemical_formula_weight         270.33
_chemical_name_systematic        2,3-diphenylbenzofuran
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-11
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r5103)
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_audit_update_record
;
2016-05-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9447(3)
_cell_length_b                   10.3826(4)
_cell_length_c                   17.0108(7)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    300
_cell_measurement_theta_max      71.2827
_cell_measurement_theta_min      4.2547
_cell_volume                     1403.16(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9614
_diffrn_measured_fraction_theta_max 0.8614
_diffrn_measurement_details
;
  1 omega  -30.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  120.0000  -61.0000 26

  2 omega  -97.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -19.0000 -120.0000 56

  3 omega  -24.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   30.0000 47

  4 omega  -49.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -120.0000 64

  5 omega   82.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1393  154.0000  -83.0000 25

  6 omega  137.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   63.0000  120.0000 29

  7 omega   46.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000   90.0000 27

  8 omega   38.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -150.0000 74

  9 omega   68.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  120.0000 25

 10 omega   38.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000 -180.0000 29

 11 omega   54.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000 -180.0000 37

 12 omega   43.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  -60.0000 42

 13 omega   43.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000    0.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0431598000
_diffrn_orient_matrix_UB_12      0.1068620000
_diffrn_orient_matrix_UB_13      -0.0595256000
_diffrn_orient_matrix_UB_21      -0.1878291000
_diffrn_orient_matrix_UB_22      -0.0124635000
_diffrn_orient_matrix_UB_23      0.0213047000
_diffrn_orient_matrix_UB_31      0.0221751000
_diffrn_orient_matrix_UB_32      0.1021360000
_diffrn_orient_matrix_UB_33      0.0648159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3193
_diffrn_reflns_theta_full        71.4234
_diffrn_reflns_theta_max         71.42
_diffrn_reflns_theta_min         4.99
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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    1.2796
_exptl_crystal_description       block
_exptl_crystal_F_000             569.6775
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.1550
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_refine_diff_density_rms         0.0566
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_d_res_high            0.8133
_refine_ls_d_res_low             8.8623
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0451
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0710P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.694
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                2022
_reflns_number_total             2350
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6qo00531d2.cif
_cod_data_source_block           exp_6157
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1553558
_chemical_oxdiff_formula         'C22 H15 O2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C4(H4), C14(H14), C13(H13), C12(H12), C11(H11),
 C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_exptl_crystal_mounting_method recrystalized
_olex2_submission_original_sample_id 'C B SRINIVAS'
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method
'mixture of dichloromethane and hexane'