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_7126568
_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         316.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.275(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.12640(10)
_cell_length_b                   13.3342(3)
_cell_length_c                   14.6256(2)
_cell_measurement_reflns_used    14090
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.4650
_cell_volume                     1582.23(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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_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     -7.00  19.00   1.00    1.00    --    0.00 -57.00  90.00   26
  2  \w    -14.00  12.00   1.00    1.00    --    0.00  57.00  30.00   26
  3  \w    -19.00  24.00   1.00    1.00    --    0.00  38.00-180.00   43
  4  \w    -80.00 -42.00   1.00    1.00    --    0.00 -57.00  90.00   38
  5  \w    -19.00  18.00   1.00    1.00    --    0.00  38.00  90.00   37
  6  \w     25.00  88.00   1.00    1.00    --    0.00  38.00-120.00   63
  7  \w     56.00  86.00   1.00    1.00    --    0.00  38.00  90.00   30
  8  \w     32.00  89.00   1.00    1.00    --    0.00  38.00-180.00   57
  9  \w    -29.00  63.00   1.00    1.00    --    0.00  77.00 -60.00   92
 10  \w     23.00  78.00   1.00    1.00    --    0.00  77.00  90.00   55
 11  \w    -19.00  17.00   1.00    1.00    --    0.00  38.00-120.00   36
 12  \w     30.00  80.00   1.00    1.00    --    0.00  57.00  30.00   50
 13  \w     52.00  82.00   1.00    1.00    --    0.00  38.00   0.00   30
 14  \w    -17.00  22.00   1.00    1.00    --    0.00  38.00   0.00   39
 15  \w    -29.00   2.00   1.00    1.00    --    0.00  77.00  90.00   31
 16  \w     65.00  97.00   1.00    2.00    --   95.80  82.00 -60.00   32
 17  \w     58.00 128.00   1.00    2.00    --   95.80 -82.00 -90.00   70
 18  \w    136.00 179.00   1.00    2.00    --   95.80  82.00-110.98   43
 19  \w     70.00 185.00   1.00    2.00    --   95.80  64.00  72.11  115
 20  \w     69.00 180.00   1.00    2.00    --   95.80  66.00  35.65  111
 21  \w     63.00  89.00   1.00    2.00    --   95.80  82.00-110.98   26
 22  \w     75.00 185.00   1.00    2.00    --   95.80  46.00 139.90  110
 23  \w     75.00 108.00   1.00    2.00    --   95.80  45.00 -60.00   33
 24  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 25  \w     63.00  88.00   1.00    2.00    --   95.80  82.00-150.00   25
 26  \w     71.00 116.00   1.00    2.00    --   95.80  61.00  90.00   45
 27  \w    155.00 185.00   1.00    2.00    --   95.80  61.00  90.00   30
 28  \w     75.00 107.00   1.00    2.00    --   95.80  45.00 -30.00   32
 29  \w    126.00 184.00   1.00    2.00    --   95.80  45.00 -30.00   58
 30  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-120.00   26
 31  \w     50.00 123.00   1.00    2.00    --   95.80 -82.00  60.00   73
 32  \w    126.00 151.00   1.00    2.00    --   95.80  76.00  24.87   25
 33  \w     32.00 127.00   1.00    2.00    --   95.80 -82.00-150.00   95
 34  \w    107.00 185.00   1.00    2.00    --   95.80  82.00 -90.00   78
 35  \w     65.00  90.00   1.00    2.00    --   95.80  76.00  24.87   25
 36  \w    154.00 179.00   1.00    2.00    --   95.80  75.00  -3.07   25
 37  \w     63.00 124.00   1.00    2.00    --   95.80 -82.00 120.00   61
 38  \w     65.00  97.00   1.00    2.00    --   95.80  82.00 -90.00   32
 39  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -30.00   26
 40  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 41  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 42  \w    141.00 167.00   1.00    2.00    --   95.80  77.00 -60.00   26
 43  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 44  \w     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 45  \w     82.00 113.00   1.00    2.00    --   95.80 -82.00   0.00   31
 46  \w     67.00  92.00   1.00    2.00    --   95.80  73.00 177.27   25
 47  \w     26.00  77.00   1.00    2.00    --   95.80 -82.00   0.00   51
 48  \w     75.00 158.00   1.00    2.00    --   95.80  45.00   0.00   83
 49  \w     72.00  98.00   1.00    2.00    --   95.80  61.00 -90.00   26
 50  \w     65.00 173.00   1.00    2.00    --   95.80  77.00-150.00  108
 51  \w     65.00  99.00   1.00    2.00    --   95.80  77.00 120.00   34
 52  \w     72.00 109.00   1.00    2.00    --   95.80  61.00   0.00   37
 53  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 -90.00   26
 54  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 150.00   25
 55  \w     63.00  88.00   1.00    2.00    --   95.80  82.00  30.00   25
 56  \w     68.00  94.00   1.00    2.00    --   95.80  82.00  60.00   26
 57  \w    122.00 179.00   1.00    2.00    --   95.80  82.00  60.00   57
 58  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 120.00   26
 59  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 60  \w    150.00 182.00   1.00    2.00    --   95.80  82.00 150.00   32
 61  \w    111.00 136.00   1.00    2.00    --   95.80  77.00   0.00   25
 62  \w     71.00  97.00   1.00    2.00    --   95.80  61.00  30.00   26
 63  \w     68.00  93.00   1.00    2.00    --   95.80  77.00   0.00   25
 64  \w     63.00 106.00   1.00    2.00    --   95.80  82.00 150.00   43
 65  \w    160.00 185.00   1.00    2.00    --   95.80  82.00 -60.00   25
 66  \w     63.00 176.00   1.00    2.00    --   95.80  81.00-165.45  113
 67  \w     71.00 106.00   1.00    2.00    --   95.80  61.00  60.00   35
 68  \w     66.00  92.00   1.00    2.00    --   95.80  75.00  -3.07   26
 69  \w     71.00 156.00   1.00    2.00    --   95.80  62.00 157.78   85
 70  \w     76.00 183.00   1.00    2.00    --   95.80  35.00 -82.24  107
;
_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      -0.0731973000
_diffrn_orient_matrix_UB_12      0.0230917000
_diffrn_orient_matrix_UB_13      -0.0972282000
_diffrn_orient_matrix_UB_21      -0.1721672000
_diffrn_orient_matrix_UB_22      0.0114705000
_diffrn_orient_matrix_UB_23      0.0376972000
_diffrn_orient_matrix_UB_31      0.0324504000
_diffrn_orient_matrix_UB_32      0.1126108000
_diffrn_orient_matrix_UB_33      0.0161399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34794
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.491
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06726
_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    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0558P)^2^+0.6493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2525
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01118e2.cif
_cod_data_source_block           exp_322
_cod_depositor_comments
'Adding full bibliography for 7126567--7126569.cif.'
_cod_database_code               7126568
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.826
_shelx_estimated_absorpt_t_min   0.736
_reflns_odcompleteness_completeness 99.93
_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:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              57956
_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 16.993
_oxdiff_exptl_absorpt_empirical_full_min 0.275