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_1553968
_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         'C26 H27 N O3'
_chemical_formula_sum            'C26 H27 N O3'
_chemical_formula_weight         401.48
_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             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-28 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                100.503(3)
_cell_angle_beta                 95.221(3)
_cell_angle_gamma                91.160(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2089(3)
_cell_length_b                   10.5763(4)
_cell_length_c                   10.9769(4)
_cell_measurement_reflns_used    5013
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5150
_cell_measurement_theta_min      4.2420
_cell_volume                     1046.09(7)
_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 0.9912
_diffrn_measured_fraction_theta_max 0.9622
_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      1.00  47.00   1.00    1.00    --   40.98 -99.00   0.00   46
  2  \w      6.00  34.00   1.00    1.00    --   40.98-103.00  44.00   28
  3  \w      2.00  69.00   1.00    1.00    --   40.98 -99.00  90.00   67
  4  \w     31.00 122.00   1.00    1.00    --  106.95 -30.00 150.00   91
  5  \w     57.00 117.00   1.00    1.00    --  106.95 -30.00  30.00   60
  6  \w     80.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   98
  7  \w    121.00 173.00   1.00    1.00    --  106.95  30.00-150.00   52
  8  \w    120.00 175.00   1.00    1.00    --  106.95 125.00-180.00   55
  9  \w     94.00 123.00   1.00    1.00    --  106.95 125.00-150.00   29
 10  \w     63.00 123.00   1.00    1.00    --  106.95 -45.00 -90.00   60
 11  \w    104.00 140.00   1.00    1.00    --  106.95 -77.00-150.00   36
 12  \w     55.00  82.00   1.00    1.00    --  106.95 -77.00-150.00   27
 13  \w     49.00 101.00   1.00    1.00    --  106.95 -94.00 -90.00   52
 14  \w     34.00 109.00   1.00    1.00    --  106.95 -94.00-180.00   75
 15  \w     33.00  78.00   1.00    1.00    --   40.98 -99.00-120.00   45
 16  \w     69.00 120.00   1.00    1.00    --  106.95-125.00  60.00   51
 17  \w     24.00  95.00   1.00    1.00    --  106.95 -94.00 120.00   71
 18  \w   -108.00 -17.00   1.00    1.00    --  -40.98 -37.00-150.00   91
 19  \w   -114.00 -36.00   1.00    1.00    --  -40.98 -37.00 120.00   78
;
_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      -0.1154897000
_diffrn_orient_matrix_UB_12      0.1009037000
_diffrn_orient_matrix_UB_13      -0.0146590000
_diffrn_orient_matrix_UB_21      0.0396325000
_diffrn_orient_matrix_UB_22      0.0658205000
_diffrn_orient_matrix_UB_23      0.1365197000
_diffrn_orient_matrix_UB_31      0.1155475000
_diffrn_orient_matrix_UB_32      0.0863925000
_diffrn_orient_matrix_UB_33      -0.0413799000
_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  0.0153
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6974
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77654
_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            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0527P)^2^+0.3612P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3797
_reflns_number_total             4070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo01122a2.cif
_cod_data_source_block           exp_187
_cod_database_code               1553968
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.853
_reflns_odcompleteness_completeness 99.12
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C16(H16), C13(H13), C10(H10), C17(H17), C15(H15), C14(H14),
 C9(H9), C23(H23), C19(H19), C20(H20), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              16519
_shelx_hkl_checksum              49106
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.636