Mechanistic Insights into the FeCl<sub>3</sub>-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes.
Vershinin, Vlada; Forkosh, Hagit; Ben-Lulu, Mor; Libman, Anna; Pappo, Doron; The Journal of organic chemistry 86 (2020) 79–90; doi:10.1021/acs.joc.0c00874

data_4038940
_publ_section_title
;
 Mechanistic Insights into the FeCl<sub>3</sub>-Catalyzed Oxidative
 Cross-Coupling of Phenols with 2-Aminonaphthalenes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              79
_journal_page_last               90
_journal_paper_doi               10.1021/acs.joc.0c00874
_journal_volume                  86
_journal_year                    2020
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_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             2020-05-21
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.620(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.93550(10)
_cell_length_b                   17.2277(2)
_cell_length_c                   10.3753(2)
_cell_measurement_reflns_used    8839
_cell_measurement_temperature    301.07(10)
_cell_measurement_theta_max      75.5290
_cell_measurement_theta_min      5.1020
_cell_volume                     1639.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      air
_diffrn_ambient_temperature      301.07(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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    -24.00  29.00   0.50    0.30    --  -46.70  19.00   0.00  106
  2  \w    -36.00  26.00   0.50    0.30    --  -46.70  38.00-120.00  124
  3  \w    -43.00 -14.00   0.50    1.21    --  -86.25  45.00-180.00   58
  4  \w    -83.00  -6.00   0.50    0.30    --  -46.70 115.00 -24.00  154
  5  \w     24.00  80.00   0.50    0.30    --   46.70  77.00-150.00  112
  6  \w     81.00 177.00   0.50    1.21    --  103.99  77.00 -60.00  192
  7  \w    101.00 177.00   0.50    1.21    --  103.99 115.00 -24.00  152
  8  \w     95.00 177.00   0.50    1.21    --  103.99 125.00 120.00  164
  9  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00  30.00   58
 10  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00   0.00   58
 11  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00 -60.00   58
 12  \w     31.00 105.00   0.50    1.21    --  103.99 -95.00 -60.00  148
 13  \w     27.00  89.00   0.50    0.30    --   46.70-115.00-113.00  124
 14  \w     34.00 112.00   0.50    1.21    --  103.99-125.00-180.00  156
 15  \w     31.00 109.00   0.50    1.21    --  103.99-115.00-113.00  156
 16  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00-150.00   58
 17  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00  60.00   58
 18  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00 120.00   58
 19  \w     32.00  61.00   0.50    1.21    --  103.99 -45.00  90.00   58
 20  \w     31.00  79.00   0.50    1.21    --  103.99 -61.00  90.00   96
 21  \w     57.00 143.00   0.50    1.21    --  103.99-169.00 102.00  172
 22  \w   -118.00 -45.00   0.50    0.30    --  -46.70-169.00 102.00  146
 23  \w   -118.00 -73.00   0.50    0.30    --  -46.70-125.00 -60.00   90
 24  \w   -118.00 -73.00   0.50    0.30    --  -46.70-125.00   0.00   90
 25  \w   -159.00 -80.00   0.50    1.21    --  -86.25-115.00-113.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0773655000
_diffrn_orient_matrix_UB_12      0.0317992000
_diffrn_orient_matrix_UB_13      -0.1492256000
_diffrn_orient_matrix_UB_21      -0.0026799000
_diffrn_orient_matrix_UB_22      -0.0822362000
_diffrn_orient_matrix_UB_23      -0.0593746000
_diffrn_orient_matrix_UB_31      -0.1490872000
_diffrn_orient_matrix_UB_32      -0.0149904000
_diffrn_orient_matrix_UB_33      0.0087622000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.987
_diffrn_reflns_theta_min         5.135
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0690P)^2^+0.2610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2841
_reflns_number_total             3333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00874_si_002.cif
_cod_data_source_block           dp_21_5_2020_19_1
_cod_depositor_comments          'Adding full bibliography for 4038940.cif.'
_cod_database_code               4038940
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H21NO2
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H00Q)=Sof(H00R)=Sof(H00S)=1-FVAR(1)
 Sof(H00N)=Sof(H00O)=Sof(H00P)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00L(H00M)
3.b Disordered Me refined with riding coordinates:
 C00M(H00N,H00O,H00P,H00Q,H00R,H00S)
3.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C), C00K(H00J,H00K,H00L), C00N(H00T,H00U,H00V)
3.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 3.376
_oxdiff_exptl_absorpt_empirical_full_min 0.496