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_7126339
_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         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.39
_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             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                87.849(4)
_cell_angle_beta                 85.541(5)
_cell_angle_gamma                72.201(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4110(5)
_cell_length_b                   9.7287(5)
_cell_length_c                   9.9501(6)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    292.49(10)
_cell_measurement_theta_max      69.4280
_cell_measurement_theta_min      4.4540
_cell_volume                     864.68(9)
_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      292.49(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
  1 omega  -79.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 28

  2 omega  -87.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 52

  3 omega  -15.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 38

  4 omega  -86.00  -60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 26

  5 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 25

  6 omega   35.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 40

  7 omega   36.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 51

  8 omega  -14.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 41

  9 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -63.0000  114.0565 27

 10 omega   88.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 33

 11 omega   -7.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -63.0000  114.0565 54

 12 omega   94.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 32

 13 omega   45.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 52

 14 omega   55.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 38

 15 omega   59.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 27

 16 omega   53.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 43

 17 omega   35.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 49

 18 omega   68.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 70

 19 omega   37.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 33

 20 omega   87.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 84

 21 omega   53.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 47

 22 omega   78.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 91

 23 omega   54.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 60

 24 omega   87.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 28

 25 omega   36.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 28

 26 omega   59.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 25

 27 omega   36.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 34

 28 omega   47.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 79

 29 omega   69.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 64

 30 omega  -87.00  -62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 25

 31 omega   69.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

 32 omega  -78.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -60.0000 91

 33 omega  -87.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 53

 34 omega  -79.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 102

 35 omega   32.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0942314000
_diffrn_orient_matrix_UB_12      -0.1205801000
_diffrn_orient_matrix_UB_13      -0.0950207000
_diffrn_orient_matrix_UB_21      -0.1218562000
_diffrn_orient_matrix_UB_22      0.0450647000
_diffrn_orient_matrix_UB_23      -0.1018025000
_diffrn_orient_matrix_UB_31      0.0772971000
_diffrn_orient_matrix_UB_32      0.1053362000
_diffrn_orient_matrix_UB_33      -0.0687747000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5442
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         4.458
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93024
_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    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0587P)^2^+0.1253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2599
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           anyang_ay223
_cod_depositor_comments
'Adding full bibliography for 7126337--7126341.cif.'
_cod_original_cell_volume        864.67(8)
_cod_database_code               7126339
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 95.54
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C13(H13), C18(H18), C19(H19), C22(H22)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              67055
_olex2_date_sample_data_collection 2019-10-08
_olex2_submission_special_instructions 'No special instructions were received'