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_7126338
_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         'C19 H19 Cl N2 O3'
_chemical_formula_sum            'C19 H19 Cl N2 O3'
_chemical_formula_weight         358.81
_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             2019-07-19
_audit_creation_method
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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                 98.755(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3251(3)
_cell_length_b                   18.1174(6)
_cell_length_c                   10.1704(4)
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    292.26(11)
_cell_measurement_theta_max      69.2520
_cell_measurement_theta_min      9.6520
_cell_volume                     1698.23(10)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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      292.26(11)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega   -2.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 30

  2 omega   33.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 30

  3 omega  -87.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 33

  4 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 45

  5 omega   65.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 57

  6 omega   68.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 57

  7 omega   72.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 40

  8 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 26

  9 omega  100.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 76

 10 omega   43.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 39

 11 omega   61.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 40

 12 omega   64.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 50

 13 omega   54.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -60.0000 78

 14 omega   52.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 41

 15 omega  109.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 41

 16 omega   88.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 73

 17 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 25

 18 omega  130.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 25

 19 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 42
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0734156000
_diffrn_orient_matrix_UB_12      0.0716139000
_diffrn_orient_matrix_UB_13      -0.0371253000
_diffrn_orient_matrix_UB_21      0.0478316000
_diffrn_orient_matrix_UB_22      0.0168615000
_diffrn_orient_matrix_UB_23      0.1486675000
_diffrn_orient_matrix_UB_31      0.1423653000
_diffrn_orient_matrix_UB_32      -0.0425996000
_diffrn_orient_matrix_UB_33      -0.0034429000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5745
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.882
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49548
_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    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.3727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2415
_reflns_number_total             2913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           any_224
_cod_depositor_comments
'Adding full bibliography for 7126337--7126341.cif.'
_cod_original_cell_volume        1698.25(10)
_cod_database_code               7126338
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 96.92
_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:
 C1(H1A,H1B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              59103
_olex2_date_sample_data_collection 2019-07-17
_olex2_submission_special_instructions 'No special instructions were received'