F+ Reagent-Promoted Pd-Catalyzed C7–H Arylation of 1-Naphthamides
Zhang, Min; Luo, Anping; Shi, Yang; Su, Rongchuan; Yang, Yudong; You, Jingsong; ACS Catalysis  (2019) 11802–; doi:10.1021/acscatal.9b04352

data_4517129
_publ_section_title
;
 F+ Reagent-Promoted Pd-Catalyzed C7--H Arylation of 1-Naphthamides
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11802
_journal_paper_doi               10.1021/acscatal.9b04352
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 N O'
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_weight         227.29
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.622(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0739(4)
_cell_length_b                   11.3132(4)
_cell_length_c                   10.2916(3)
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    296.0(5)
_cell_measurement_theta_max      72.4290
_cell_measurement_theta_min      5.8180
_cell_volume                     1286.77(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      296.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  2 omega  -31.00   63.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  150.0000 94

  3 omega  -33.00   55.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  120.0000 88

  4 omega    1.00   75.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  5 omega   20.00  104.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  6 omega  -31.00   53.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -90.0000 84

  7 omega   38.00   91.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

  8 omega   39.00  109.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

  9 omega   38.00  116.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 10 omega  100.00  178.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 11 omega   38.00   91.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 12 omega   38.00   91.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 13 omega   39.00  109.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 14 omega   90.00  175.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 15 omega   41.00  126.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 85

 16 omega   90.00  175.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

 17 omega   10.00   63.00   1.0000    1.3900
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1272632000
_diffrn_orient_matrix_UB_12      -0.0538981000
_diffrn_orient_matrix_UB_13      -0.0057156000
_diffrn_orient_matrix_UB_21      0.0553691000
_diffrn_orient_matrix_UB_22      0.1250063000
_diffrn_orient_matrix_UB_23      0.0027725000
_diffrn_orient_matrix_UB_31      0.0126206000
_diffrn_orient_matrix_UB_32      -0.0043669000
_diffrn_orient_matrix_UB_33      0.1498652000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7299
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.639
_diffrn_reflns_theta_min         5.818
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0643
_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^)+(0.1228P)^2^+0.1106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2127
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04352_si_002.cif
_cod_data_source_block           yjs-zm--1
_cod_original_cell_volume        1286.76(7)
_cod_database_code               4517129
_reflns_odcompleteness_completeness 99.79
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C008(H008), C00C(H00G), C00D(H00H), C00E(H00I),
 C00F(H00J), C00G(H00K)
2.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00B(H00D,H00E,H00F), C00H(H00L,H00M,H00N)
;
_shelx_res_checksum              37558
_shelx_hkl_checksum              87141
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-22
_olex2_submission_special_instructions 'No special instructions were received'