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_7126337
_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 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39
_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             2019-07-19
_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                 108.1425(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7868(3)
_cell_length_b                   9.84896(13)
_cell_length_c                   19.3586(3)
_cell_measurement_reflns_used    10414
_cell_measurement_temperature    292.39(14)
_cell_measurement_theta_max      69.7460
_cell_measurement_theta_min      6.4520
_cell_volume                     3403.85(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      292.39(14)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -60.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000   90.0000 59

  2 omega  -39.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -150.0000 36

  3 omega  -70.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000 -150.0000 85

  4 omega  -86.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

  5 omega   32.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 91

  6 omega   39.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 88

  7 omega    1.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  120.0000 92

  8 omega  -13.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 85

  9 omega  125.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 50

 10 omega   34.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 74

 11 omega   72.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -180.0000 65

 12 omega   36.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 57

 13 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 26

 14 omega   38.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 39

 15 omega  101.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 44

 16 omega   74.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 40

 17 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 26

 18 omega   79.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 67

 19 omega   36.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   60.0000 110

 20 omega   67.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 37

 21 omega   35.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 77

 22 omega   35.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 58

 23 omega   79.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25

 24 omega   45.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27

 25 omega   45.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 58

 26 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 26

 27 omega   58.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 36

 28 omega   49.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 40

 29 omega   47.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 30

 30 omega   70.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   90.0000 103

 31 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 25

 32 omega   99.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 26

 33 omega   60.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0217927000
_diffrn_orient_matrix_UB_12      0.1032965000
_diffrn_orient_matrix_UB_13      -0.0628859000
_diffrn_orient_matrix_UB_21      -0.0020056000
_diffrn_orient_matrix_UB_22      -0.1150555000
_diffrn_orient_matrix_UB_23      -0.0544967000
_diffrn_orient_matrix_UB_31      -0.0834460000
_diffrn_orient_matrix_UB_32      -0.0241850000
_diffrn_orient_matrix_UB_33      -0.0092197000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24742
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.672
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44863
_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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0529P)^2^+0.6645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5298
_reflns_number_total             5971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           any211_0711
_cod_depositor_comments
;
Adding full bibliography for 7126337--7126341.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3403.86(9)
_cod_original_formula_moiety     '2(C20 H22 N2 O2)'
_cod_original_formula_sum        'C40 H44 N4 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     644.79
_cod_database_code               7126337
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.15
_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:
 C9(H9A,H9B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B),
  C46(H46A,H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C23(H23), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C41(H41), C45(H45)
2.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              93287
_olex2_date_sample_data_collection 2019-07-11
_olex2_submission_special_instructions 'No special instructions were received'