Switching the regioselectivity of acid-catalyzed reactions of arylnaphtho[2,1-<i>b</i>]furans <i>via</i> a [1,2]-aryl shift.
Mekeda, I. S.; Balakhonov, R. Yu; Shirinian, V. Z.; Organic & biomolecular chemistry 22 (2024) 7715–7724; doi:10.1039/d4ob01223b

data_7160112
_publ_section_title
;
 Switching the regioselectivity of acid-catalyzed reactions of
 arylnaphtho[2,1-<i>b</i>]furans <i>via</i> a [1,2]-aryl shift.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7715
_journal_page_last               7724
_journal_paper_doi               10.1039/d4ob01223b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C36 H22 O2'
_chemical_formula_sum            'C36 H22 O2'
_chemical_formula_weight         486.53
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-01-09
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9186(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.43259(10)
_cell_length_b                   24.93811(18)
_cell_length_c                   8.39634(6)
_cell_measurement_reflns_used    20304
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2510
_cell_measurement_theta_min      3.9110
_cell_volume                     2376.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -27.00  22.00   0.50    0.65    --  -46.59  95.00 124.00   98
  2  \w    -79.00 -46.00   0.50    0.65    --  -46.59  95.00 124.00   66
  3  \w     -9.00  57.00   0.50    0.65    --   46.59 -95.00  14.00  132
  4  \w    -50.00 -25.00   0.50    2.60    --  -91.75  95.00 124.00   50
  5  \w    105.00 144.00   0.50    2.60    --  113.25  95.00 124.00   78
  6  \w     80.00 106.00   0.50    2.60    --  113.25 -95.00  14.00   52
  7  \w    -43.00  27.00   0.50    0.65    --  -46.59  38.00-120.00  140
  8  \w    -27.00  29.00   0.50    0.65    --  -46.59  19.00 120.00  112
  9  \w    -26.00  27.00   0.50    0.65    --   46.59 -19.00 -90.00  106
 10  \w    -51.00 -26.00   0.50    2.60    --  -91.75  45.00 -30.00   50
 11  \w    -50.00 -20.00   0.50    2.60    --  -91.75  45.00 -90.00   60
 12  \w   -148.00-123.00   0.50    2.60    --  -91.75 -95.00  14.00   50
 13  \w    127.00 168.00   0.50    2.60    --  113.25  45.00-150.00   82
 14  \w     44.00  70.00   0.50    2.60    --  113.25 -61.00   0.00   52
 15  \w     41.00  70.00   0.50    2.60    --  113.25 -61.00-120.00   58
 16  \w     98.00 125.00   0.50    2.60    --  113.25  15.00   0.00   54
 17  \w    141.00 176.00   0.50    2.60    --  113.25  15.00   0.00   70
 18  \w     65.00  96.00   0.50    2.60    --  113.25 -77.00-120.00   62
 19  \w     50.00  95.00   0.50    2.60    --  113.25 -87.00  87.04   90
 20  \w     43.00  68.00   0.50    2.60    --  113.25 -95.00 150.00   50
 21  \w     61.00  99.00   0.50    2.60    --  113.25 -95.00  60.00   76
 22  \w     41.00  71.00   0.50    2.60    --  113.25 -61.00 -90.00   60
 23  \w     46.00 106.00   0.50    2.60    --  113.25 -95.00-180.00  120
 24  \w    133.00 171.00   0.50    2.60    --  113.25  61.00-120.00   76
 25  \w     47.00 102.00   0.50    2.60    --  113.25 -95.00 -30.00  110
 26  \w     99.00 125.00   0.50    2.60    --  113.25  77.00   0.00   52
 27  \w    104.00 176.00   0.50    2.60    --  113.25  61.00  60.00  144
 28  \w     41.00  67.00   0.50    2.60    --  113.25 -77.00-180.00   52
 29  \w     75.00 104.00   0.50    2.60    --  113.25 -77.00-180.00   58
 30  \w     42.00  94.00   0.50    2.60    --  113.25 -84.00  45.32  104
 31  \w     51.00 100.00   0.50    2.60    --  113.25 -95.00  90.00   98
 32  \w    140.00 166.00   0.50    2.60    --  113.25  30.00-150.00   52
 33  \w    104.00 140.00   0.50    2.60    --  113.25 -85.00  54.12   72
 34  \w     42.00  67.00   0.50    2.60    --  113.25 -95.00   0.00   50
 35  \w    109.00 154.00   0.50    2.60    --  113.25  15.00 -30.00   90
 36  \w     64.00  89.00   0.50    2.60    --  113.25-125.00 -90.00   50
 37  \w     99.00 125.00   0.50    2.60    --  113.25  61.00-120.00   52
 38  \w     46.00  72.00   0.50    2.60    --  113.25 -85.00  54.12   52
 39  \w     97.00 155.00   0.50    2.60    --  113.25  77.00-120.00  116
 40  \w     78.00 104.00   0.50    2.60    --  113.25 -95.00 150.00   52
 41  \w     47.00  73.00   0.50    2.60    --  113.25-125.00-150.00   52
 42  \w     46.00  80.00   0.50    2.60    --  113.25-125.00  60.00   68
 43  \w    100.00 126.00   0.50    2.60    --  113.25  45.00 -90.00   52
 44  \w    144.00 177.00   0.50    2.60    --  113.25  45.00 -90.00   66
 45  \w    124.00 150.00   0.50    2.60    --  113.25  30.00  60.00   52
 46  \w    116.00 142.00   0.50    2.60    --  113.25 125.00  30.00   52
 47  \w     41.00  66.00   0.50    2.60    --  113.25 -61.00  90.00   50
 48  \w     41.00  72.00   0.50    2.60    --  113.25 -79.00  -9.91   62
 49  \w    106.00 132.00   0.50    2.60    --  113.25 -79.00  -9.91   52
 50  \w     47.00  76.00   0.50    2.60    --  113.25 -88.00-164.26   58
 51  \w     99.00 141.00   0.50    2.60    --  113.25 -88.00-164.26   84
 52  \w     42.00  71.00   0.50    2.60    --  113.25 -61.00  30.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1172108000
_diffrn_orient_matrix_UB_12      0.0201795000
_diffrn_orient_matrix_UB_13      0.0512453000
_diffrn_orient_matrix_UB_21      0.0164474000
_diffrn_orient_matrix_UB_22      0.0539788000
_diffrn_orient_matrix_UB_23      -0.0836365000
_diffrn_orient_matrix_UB_31      -0.0664345000
_diffrn_orient_matrix_UB_32      -0.0222004000
_diffrn_orient_matrix_UB_33      -0.1567467000
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28404
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.775
_diffrn_reflns_theta_min         3.545
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0407P)^2^+0.8642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4778
_reflns_number_total             5163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01223b2.cif
_cod_data_source_block           ME-209
_cod_depositor_comments          'Adding full bibliography for 7160112.cif.'
_cod_original_cell_volume        2376.42(3)
_cod_database_code               7160112
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C36H22O2
_chemical_oxdiff_usercomment     ME-209
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 98.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;
_shelx_res_checksum              17939
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.864