Gold-catalyzed intermolecular [4+1] spiroannulation via site-selective aromatic C(sp<sup>2</sup>)-H functionalization and dearomatization of phenol derivatives.
Li, Yongfeng; Tang, Zhiqiong; Zhang, Junliang; Liu, Lu; Chemical communications (Cambridge, England) 56 (2020) 8202–8205; doi:10.1039/d0cc01118e

data_7126569
_publ_section_title
;
 Gold-catalyzed intermolecular [4+1] spiroannulation via site-selective
 aromatic C(sp<sup>2</sup>)-H functionalization and dearomatization of
 phenol derivatives.
;
_journal_issue                   59
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8202
_journal_page_last               8205
_journal_paper_doi               10.1039/d0cc01118e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                88.0490(10)
_cell_angle_beta                 84.2170(10)
_cell_angle_gamma                86.2990(10)
_cell_formula_units_Z            4
_cell_length_a                   10.5466(2)
_cell_length_b                   10.5720(2)
_cell_length_c                   14.2364(2)
_cell_measurement_reflns_used    26828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1210
_cell_measurement_theta_min      4.1920
_cell_volume                     1575.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_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    -19.00  24.00   1.00    1.00    --    0.00  38.00 -30.00   43
  2  \w      5.00  61.00   1.00    1.00    --    0.00  38.00-180.00   56
  3  \w    -29.00  -3.00   1.00    1.00    --    0.00  82.00-180.00   26
  4  \w     14.00  65.00   1.00    1.00    --    0.00  77.00 120.00   51
  5  \w     53.00  81.00   1.00    1.00    --    0.00  38.00  30.00   28
  6  \w    -14.00  41.00   1.00    1.00    --    0.00  38.00  30.00   55
  7  \w     52.00  88.00   1.00    1.00    --    0.00  19.00 -60.00   36
  8  \w    -18.00  13.00   1.00    1.00    --    0.00  38.00  90.00   31
  9  \w    -23.00  35.00   1.00    1.00    --    0.00  19.00 -60.00   58
 10  \w    -26.00  11.00   1.00    1.00    --    0.00  77.00 120.00   37
 11  \w    -12.00  19.00   1.00    1.00    --    0.00 -38.00 150.00   31
 12  \w    -65.00 -20.00   1.00    1.00    --    0.00 -38.00 150.00   45
 13  \w     23.00  87.00   1.00    1.00    --    0.00  82.00-180.00   64
 14  \w     29.00  79.00   1.00    1.00    --    0.00  38.00  90.00   50
 15  \w     36.00  62.00   1.00    1.00    --    0.00  38.00 -30.00   26
 16  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  122
 17  \w     87.00 125.00   1.00    1.00    --   95.80 -82.00 -30.00   38
 18  \w    155.00 181.00   1.00    1.00    --   95.80  79.00 163.51   26
 19  \w      7.00  79.00   1.00    1.00    --   95.80 -82.00 -30.00   72
 20  \w     75.00 132.00   1.00    1.00    --   95.80  45.00 -60.00   57
 21  \w     64.00  90.00   1.00    1.00    --   95.80  79.00 163.51   26
 22  \w     70.00 183.00   1.00    1.00    --   95.80  63.00 164.45  113
 23  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 24  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 25  \w     64.00  98.00   1.00    1.00    --   95.80  82.00 -60.00   34
 26  \w     66.00  92.00   1.00    1.00    --   95.80  82.00-120.00   26
 27  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 30  \w     78.00 130.00   1.00    1.00    --   95.80  30.00 120.00   52
 31  \w     86.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   42
 32  \w     24.00 101.00   1.00    1.00    --   95.80 -61.00 150.00   77
 33  \w    158.00 184.00   1.00    1.00    --   95.80  77.00 120.00   26
 34  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 35  \w    125.00 184.00   1.00    1.00    --   95.80  80.00  17.73   59
 36  \w    140.00 166.00   1.00    1.00    --   95.80  60.00  72.97   26
 37  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 38  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 39  \w     52.00 103.00   1.00    1.00    --   95.80 -82.00  90.00   51
 40  \w     76.00 182.00   1.00    1.00    --   95.80  45.00 120.00  106
 41  \w     71.00  96.00   1.00    1.00    --   95.80  61.00 -60.00   25
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 43  \w     63.00 132.00   1.00    1.00    --   95.80  82.00  30.00   69
 44  \w     64.00  97.00   1.00    1.00    --   95.80  82.00  60.00   33
 45  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 47  \w    136.00 162.00   1.00    1.00    --   95.80  82.00-150.00   26
 48  \w     64.00  89.00   1.00    1.00    --   95.80  82.00  90.00   25
 49  \w    108.00 171.00   1.00    1.00    --   95.80  61.00-120.00   63
 50  \w     43.00  87.00   1.00    1.00    --   95.80 -82.00 -60.00   44
 51  \w     97.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   31
 52  \w     64.00 101.00   1.00    1.00    --   95.80  80.00  17.73   37
 53  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 54  \w     76.00 112.00   1.00    1.00    --   95.80  45.00 150.00   36
 55  \w    134.00 178.00   1.00    1.00    --   95.80  45.00 150.00   44
 56  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 57  \w     71.00 100.00   1.00    1.00    --   95.80  61.00-120.00   29
 58  \w     65.00 177.00   1.00    1.00    --   95.80  77.00-180.00  112
 59  \w     75.00 173.00   1.00    1.00    --   95.80  45.00   0.00   98
 60  \w     77.00 181.00   1.00    1.00    --   95.80  45.00 -30.00  104
 61  \w     68.00 118.00   1.00    1.00    --   95.80  68.00   3.15   50
 62  \w     71.00 105.00   1.00    1.00    --   95.80  60.00  72.97   34
 63  \w     70.00 182.00   1.00    1.00    --   95.80  63.00-106.81  112
 64  \w     12.00 119.00   1.00    1.00    --   95.80 -82.00 -90.00  107
 65  \w     69.00 184.00   1.00    1.00    --   95.80  67.00-147.14  115
;
_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      -0.0634768000
_diffrn_orient_matrix_UB_12      0.0166251000
_diffrn_orient_matrix_UB_13      -0.0928414000
_diffrn_orient_matrix_UB_21      0.1307633000
_diffrn_orient_matrix_UB_22      -0.0266556000
_diffrn_orient_matrix_UB_23      -0.0566705000
_diffrn_orient_matrix_UB_31      -0.0225696000
_diffrn_orient_matrix_UB_32      -0.1426635000
_diffrn_orient_matrix_UB_33      0.0028606000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37195
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.357
_diffrn_reflns_theta_min         4.192
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0477P)^2^+0.7482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6047
_reflns_number_total             6305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01118e2.cif
_cod_data_source_block           exp_624
_cod_depositor_comments
;
Adding full bibliography for 7126567--7126569.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H16 O3)'
_cod_original_formula_sum        'C42 H32 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     632.67
_cod_database_code               7126569
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C37(H37)
2.c X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C42(H42A,H42B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              32632
_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 4.574
_oxdiff_exptl_absorpt_empirical_full_min 0.490