Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated <i>N</i>-alkylanilines in water.
Hikawa, Hidemasa; Fukuda, Akane; Kondo, Kazuma; Nakayama, Taku; Enda, Tomokatsu; Kikkawa, Shoko; Azumaya, Isao; Organic & biomolecular chemistry 22 (2024) 7874–7879; doi:10.1039/d4ob01234h

data_7160123
_publ_section_title
;
 Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated
 <i>N</i>-alkylanilines in water.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7874
_journal_page_last               7879
_journal_paper_doi               10.1039/d4ob01234h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H18 N2 O2'
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.219(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4437(5)
_cell_length_b                   5.5419(2)
_cell_length_c                   20.4328(6)
_cell_measurement_reflns_used    7114
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.2510
_cell_measurement_theta_min      3.6370
_cell_volume                     1628.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -99.00  81.00   0.50    5.00    --   -9.00  55.00-180.00  360
  2  \w    -99.00  54.00   0.50    5.00    --   -9.00  55.00  90.00  306
  3  \w     23.00  61.00   0.50    5.00    --   -9.00   0.00-180.00   76
  4  \w    -99.00  81.00   0.50    5.00    --   -9.00   0.00   0.00  360
  5  \w    -99.00 -69.00   0.50    5.00    --   -9.00  27.00-180.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0192575000
_diffrn_orient_matrix_UB_12      -0.0259986000
_diffrn_orient_matrix_UB_13      0.0299346000
_diffrn_orient_matrix_UB_21      0.0413226000
_diffrn_orient_matrix_UB_22      0.0415847000
_diffrn_orient_matrix_UB_23      0.0178550000
_diffrn_orient_matrix_UB_31      -0.0188021000
_diffrn_orient_matrix_UB_32      0.1182204000
_diffrn_orient_matrix_UB_33      0.0002722000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24796
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.832
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0507P)^2^+0.4886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2825
_reflns_number_total             3743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01234h2.cif
_cod_data_source_block           afu012_c_acoet_meoh
_cod_depositor_comments          'Adding full bibliography for 7160123.cif.'
_cod_database_code               7160123
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C19(H19), C13(H13), C15(H15), C16(H16), C10(H10),
 C11(H11), C6(H6), C17(H17), C12(H12), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              76636
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.779