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_7126567
_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             2018-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.039(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2055(2)
_cell_length_b                   17.4289(3)
_cell_length_c                   10.2408(2)
_cell_measurement_reflns_used    7516
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0270
_cell_measurement_theta_min      4.9930
_cell_volume                     1642.01(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -26.00  19.00   1.00    1.00    --    0.00 -57.00   0.00   45
  2  \w     62.00  89.00   1.00    1.00    --    0.00  38.00-120.00   27
  3  \w    -45.00 -19.00   1.00    1.00    --    0.00 -57.00 120.00   26
  4  \w    -87.00 -34.00   1.00    1.00    --    0.00 -57.00   0.00   53
  5  \w    -67.00  16.00   1.00    1.00    --    0.00 -19.00-120.00   83
  6  \w    -19.00  45.00   1.00    1.00    --    0.00  38.00-120.00   64
  7  \w      6.00  61.00   1.00    1.00    --   95.80 -77.00 -90.00   55
  8  \w    117.00 184.00   1.00    1.00    --   95.80  30.00  90.00   67
  9  \w      6.00  99.00   1.00    1.00    --   95.80 -45.00 -90.00   93
 10  \w     69.00 101.00   1.00    1.00    --   95.80 -82.00 -90.00   32
 11  \w     36.00 121.00   1.00    1.00    --   95.80 -82.00  30.00   85
 12  \w     79.00 104.00   1.00    1.00    --   95.80  30.00   0.00   25
 13  \w    122.00 185.00   1.00    1.00    --   95.80  30.00   0.00   63
 14  \w     38.00  64.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 15  \w     18.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  110
 16  \w     28.00 119.00   1.00    1.00    --   95.80 -15.00   0.00   91
 17  \w     14.00 118.00   1.00    1.00    --   95.80 -61.00 150.00  104
 18  \w     21.00 106.00   1.00    1.00    --   95.80 -61.00  30.00   85
 19  \w     82.00 107.00   1.00    1.00    --   95.80 -77.00 -90.00   25
 20  \w     80.00 105.00   1.00    1.00    --   95.80 -82.00 -60.00   25
 21  \w     76.00 184.00   1.00    1.00    --   95.80  30.00  30.00  108
 22  \w    126.00 152.00   1.00    1.00    --   95.80  30.00 -90.00   26
 23  \w     78.00 103.00   1.00    1.00    --   95.80 -82.00  90.00   25
;
_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      -0.0233122000
_diffrn_orient_matrix_UB_12      -0.0303541000
_diffrn_orient_matrix_UB_13      -0.1404501000
_diffrn_orient_matrix_UB_21      0.0217054000
_diffrn_orient_matrix_UB_22      -0.0827386000
_diffrn_orient_matrix_UB_23      0.0498351000
_diffrn_orient_matrix_UB_31      -0.1644463000
_diffrn_orient_matrix_UB_32      -0.0066504000
_diffrn_orient_matrix_UB_33      0.0210343000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15545
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         5.011
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66201
_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    1.280
_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         0.167
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0500P)^2^+0.2580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2505
_reflns_number_total             2918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01118e2.cif
_cod_data_source_block           exp_303
_cod_depositor_comments
'Adding full bibliography for 7126567--7126569.cif.'
_cod_database_code               7126567
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.744
_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:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C11(H11), C16(H16), C3(H3), C14(H14), C12(H12), C13(H13), C6(H6),
 C4(H4), C5(H5)
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              42461
_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 2.553
_oxdiff_exptl_absorpt_empirical_full_min 0.450