Palladium-Catalyzed Regioselective C8-H Amination of 1-Naphthylamine Derivatives with Aliphatic Amines.
Li, Zexian; Sun, Suyan; Qiao, Huijie; Yang, Fan; Zhu, Yu; Kang, Jianxun; Wu, Yusheng; Wu, Yangjie; Organic letters 18 (2016) 4594–4597; doi:10.1021/acs.orglett.6b02243

data_1555728
_publ_section_title
;
 Palladium-Catalyzed Regioselective C8-H Amination of 1-Naphthylamine
 Derivatives with Aliphatic Amines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4594
_journal_page_last               4597
_journal_paper_doi               10.1021/acs.orglett.6b02243
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38
_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             2016-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                85.819(10)
_cell_angle_beta                 88.672(10)
_cell_angle_gamma                77.281(11)
_cell_formula_units_Z            2
_cell_length_a                   8.9053(11)
_cell_length_b                   9.1342(11)
_cell_length_c                   10.3857(12)
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6040
_cell_measurement_theta_min      3.6000
_cell_volume                     821.86(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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    -25.00  24.00   1.00    1.00    --  -15.33 -99.00 -60.00   49
  2  \w    -25.00  24.00   1.00    1.00    --  -15.33 -99.00 -90.00   49
  3  \w    -40.00  32.00   1.00    1.00    --   18.22 -57.00 -60.00   72
  4  \w     -9.00  83.00   1.00    1.00    --   18.22  77.00-180.00   92
  5  \w    -38.00   5.00   1.00    1.00    --   18.22 -57.00 -90.00   43
  6  \w    -49.00  45.00   1.00    1.00    --   18.22 -77.00  60.00   94
  7  \w    -82.00 -29.00   1.00    5.00    --  -15.18 -57.00 -90.00   53
  8  \w     32.00  91.00   1.00    5.00    --   18.07-178.00 -90.00   59
  9  \w     -1.00  87.00   1.00    5.00    --   18.07  37.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0252238000
_diffrn_orient_matrix_UB_12      0.0310237000
_diffrn_orient_matrix_UB_13      0.0594553000
_diffrn_orient_matrix_UB_21      -0.0025074000
_diffrn_orient_matrix_UB_22      0.0732819000
_diffrn_orient_matrix_UB_23      -0.0289059000
_diffrn_orient_matrix_UB_31      -0.0776207000
_diffrn_orient_matrix_UB_32      0.0059461000
_diffrn_orient_matrix_UB_33      -0.0178599000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9866
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.402
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0520
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2224
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02243_si_002.cif
_cod_data_source_block           20160339
_cod_original_cell_volume        821.86(18)
_cod_database_code               1555728
_chemical_oxdiff_formula         C1H1N1O1
_reflns_odcompleteness_completeness 99.76
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), N2(H2A)
;
_shelx_res_checksum              77178
_shelx_hkl_checksum              50053
_shelx_shelxl_version_number     2014/7
_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 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.804