A silver-catalyzed three-component reaction via stabilized cation: synthesis of polysubstituted tetrahydronaphthols and tetrahydronaphthylamines
Luo, Hejiang; Liang, Renxiao; Chen, Lianfen; Jiang, Huanfeng; Zhu, Shifa; Organic Chemistry Frontiers 5 (2018) 1160–; doi:10.1039/C7QO01122A

data_1553969
_publ_section_title
;
 A silver-catalyzed three-component reaction via stabilized cation:
 synthesis of polysubstituted tetrahydronaphthols and
 tetrahydronaphthylamines
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1160
_journal_paper_doi               10.1039/C7QO01122A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C23 H19 F O2'
_chemical_formula_sum            'C23 H19 F O2'
_chemical_formula_weight         346.38
_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     direct
_audit_creation_date             2017-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                75.074(5)
_cell_angle_beta                 77.458(5)
_cell_angle_gamma                63.345(5)
_cell_formula_units_Z            2
_cell_length_a                   8.9683(5)
_cell_length_b                   9.8217(5)
_cell_length_c                   11.3530(7)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.2160
_cell_measurement_theta_min      2.5600
_cell_volume                     857.59(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.880
_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     15.00  84.00   1.00    1.00    --   11.74  57.00   0.00   69
  2  \w     44.00  86.00   1.00    1.00    --   11.74  37.00 -60.00   42
  3  \w    -12.00  84.00   1.00    1.00    --   11.74  37.00 120.00   96
  4  \w    -18.00  53.00   1.00    1.00    --   11.74 -99.00  60.00   71
  5  \w    -46.00  40.00   1.00    1.00    --   11.74 -57.00 -60.00   86
  6  \w    -20.00  53.00   1.00    1.00    --   11.74 -99.00-180.00   73
  7  \w    -19.00  86.00   1.00    1.00    --   11.74  77.00-150.00  105
  8  \w     37.00  77.00   1.00    1.00    --   11.74 178.00 -30.00   40
  9  \w    -83.00 -52.00   1.00    1.00    --  -11.59 149.00 149.62   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0695997000
_diffrn_orient_matrix_UB_12      -0.0094415000
_diffrn_orient_matrix_UB_13      0.0387030000
_diffrn_orient_matrix_UB_21      0.0334388000
_diffrn_orient_matrix_UB_22      -0.0022634000
_diffrn_orient_matrix_UB_23      0.0520006000
_diffrn_orient_matrix_UB_31      -0.0444862000
_diffrn_orient_matrix_UB_32      0.0816270000
_diffrn_orient_matrix_UB_33      -0.0061180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14359
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.529
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0471P)^2^+0.2440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3211
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo01122a2.cif
_cod_data_source_block           106-4-2
_cod_original_cell_volume        857.58(9)
_cod_database_code               1553969
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C4(H4), C19(H19), C14(H14), C1(H1A), C2(H2), C16(H16),
 C20(H20), C15(H15), C23(H23), C3(H3), C22(H22)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.479