A carboxylate-assisted amination/unactivated C(sp<sup>2</sup>)-H arylation reaction via a palladium/norbornene cooperative catalysis.
An, Yang; Zhang, Bo-Sheng; Zhang, Zhe; Liu, Ce; Gou, Xue-Ya; Ding, Ya-Nan; Liang, Yong-Min; Chemical communications (Cambridge, England) 56 (2020) 5933–5936; doi:10.1039/c9cc09265j

data_7126340
_publ_section_title
;
 A carboxylate-assisted amination/unactivated C(sp<sup>2</sup>)-H
 arylation reaction via a palladium/norbornene cooperative catalysis.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5933
_journal_page_last               5936
_journal_paper_doi               10.1039/c9cc09265j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C17 H16 F N O2'
_chemical_formula_sum            'C17 H16 F N O2'
_chemical_formula_weight         285.31
_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     direct
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.406(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1703(5)
_cell_length_b                   9.1104(2)
_cell_length_c                   19.1959(6)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    292.59(10)
_cell_measurement_theta_max      69.8640
_cell_measurement_theta_min      7.5500
_cell_volume                     2712.38(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      292.59(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   -9.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 27

  2 omega   27.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 28

  3 omega  -83.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 49

  4 omega   33.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 79

  5 omega   69.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 28

  6 omega   87.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 32

  7 omega    2.00   53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 51

  8 omega   68.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 57

  9 omega   41.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 90

 10 omega   37.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 29

 11 omega   43.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 27

 12 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

 13 omega   37.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

 14 omega  144.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 30

 15 omega   64.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

 16 omega   41.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 91

 17 omega   91.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 83

 18 omega   85.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 26

 19 omega   44.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 69

 20 omega   43.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 29

 21 omega   69.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0164139000
_diffrn_orient_matrix_UB_12      0.0134090000
_diffrn_orient_matrix_UB_13      0.0725922000
_diffrn_orient_matrix_UB_21      0.0798651000
_diffrn_orient_matrix_UB_22      -0.0957929000
_diffrn_orient_matrix_UB_23      0.0451189000
_diffrn_orient_matrix_UB_31      0.0567133000
_diffrn_orient_matrix_UB_32      0.1387517000
_diffrn_orient_matrix_UB_33      0.0241632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10281
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.568
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0480P)^2^+0.3809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3489
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           anyang_2
_cod_depositor_comments
'Adding full bibliography for 7126337--7126341.cif.'
_cod_original_cell_volume        2712.40(16)
_cod_database_code               7126340
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.70
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C23(H23A,H23B), C26(H26A,H26B), C28(H28A,H28B),
 C29(H29A,H29B), C33(H33A,H33B), C36(H36A,H36B), C37(H37A,H37B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C24(H24), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C38(H38), C39(H39), C40(H40), C0AA(H0AA)
;
_shelx_res_checksum              83117
_olex2_date_sample_data_collection 2019-10-08
_olex2_submission_special_instructions 'No special instructions were received'