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_1553557
_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_formula_moiety         'C25 H18 O2'
_chemical_formula_sum            'C25 H18 O2'
_chemical_formula_weight         350.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P -2ac -2n'
_space_group_name_H-M_alt        'P n 21 a'
_symmetry_Int_Tables_number      33
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-21 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                   14.3717(6)
_cell_length_b                   5.9170(2)
_cell_length_c                   21.4597(9)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    300
_cell_measurement_theta_max      70.9993
_cell_measurement_theta_min      3.0733
_cell_volume                     1824.88(12)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
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)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_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 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_details
;
  1 omega  -64.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 29

  2 omega  -66.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   20.0000   39.0000 77

  3 omega   41.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -113.0000  130.0000 54

  4 omega   70.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 41

  5 omega   77.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 44

  6 omega   49.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 36

  7 omega  113.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 36

  8 omega   41.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 60

  9 omega   39.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 125

 10 omega -101.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000    0.0000 89

 11 omega -103.00   -5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0029318000
_diffrn_orient_matrix_UB_12      0.0510137000
_diffrn_orient_matrix_UB_13      -0.0703606000
_diffrn_orient_matrix_UB_21      -0.1052512000
_diffrn_orient_matrix_UB_22      -0.0470783000
_diffrn_orient_matrix_UB_23      -0.0045827000
_diffrn_orient_matrix_UB_31      -0.0203739000
_diffrn_orient_matrix_UB_32      0.2508397000
_diffrn_orient_matrix_UB_33      0.0134677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5075
_diffrn_reflns_theta_full        71.0934
_diffrn_reflns_theta_max         71.09
_diffrn_reflns_theta_min         3.70
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81730
_exptl_absorpt_correction_type   gaussian
_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            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             738.2524
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2273
_refine_diff_density_min         -0.3235
_refine_diff_density_rms         0.0629
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.8(4)
_refine_ls_d_res_high            0.8149
_refine_ls_d_res_low             11.9412
_refine_ls_goodness_of_fit_ref   1.0503
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0503
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0910P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1967
_reflns_Friedel_coverage         0.325
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              7
_reflns_limit_k_min              -4
_reflns_limit_l_max              25
_reflns_limit_l_min              -23
_reflns_number_gt                1444
_reflns_number_total             2374
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6qo00531d2.cif
_cod_data_source_block           exp_6269
_cod_original_cell_volume        1824.88(13)
_cod_original_sg_symbol_Hall     ' P 2c -2n (-x,z,y)'
_cod_database_code               1553557
_chemical_oxdiff_formula         'C20 H20 O2'
_reflns_odcompleteness_completeness 97.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C6(H6),
 C5(H5), C4(H4), C3(H3), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_olex2_submission_special_instructions 'No special instructions were received'