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_7126341
_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 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.31
_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             2019-07-01
_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                 97.119(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9106(5)
_cell_length_b                   6.1532(3)
_cell_length_c                   37.0164(17)
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    173.20(10)
_cell_measurement_theta_max      69.9510
_cell_measurement_theta_min      8.6220
_cell_volume                     2692.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      173.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     38.00 111.00   1.00    3.00    --  108.00 -50.00  90.00   73
  2  \w     97.00 168.00   1.00    3.00    --  108.00  38.00 -30.00   71
  3  \w    151.00 176.00   1.00    3.00    --  108.00  61.00  18.00   25
  4  \w    102.00 137.00   1.00    3.00    --  108.00 111.00-120.00   35
  5  \w     93.00 168.00   1.00    3.00    --  108.00  63.00   0.00   75
  6  \w     39.00 134.00   1.00    3.00    --  108.00 -77.00-120.00   95
  7  \w     36.00 129.00   1.00    3.00    --  108.00  12.00-180.00   93
  8  \w     28.00 125.00   1.00    2.00    --   54.00  38.00   0.00   97
  9  \w     34.00  61.00   1.00    1.00    --    0.00  57.00-150.00   27
 10  \w    -14.00  11.00   1.00    1.00    --    0.00  57.00-150.00   25
 11  \w    -18.00  78.00   1.00    2.00    --   54.00 -38.00-180.00   96
 12  \w     28.00  54.00   1.00    2.00    --   54.00 -77.00-180.00   26
 13  \w     26.00  75.00   1.00    2.00    --   54.00-125.00-180.00   49
 14  \w    -20.00  13.00   1.00    1.00    --    0.00 -57.00 -90.00   33
 15  \w    -62.00 -35.00   1.00    1.00    --    0.00 -57.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1064094000
_diffrn_orient_matrix_UB_12      0.1115848000
_diffrn_orient_matrix_UB_13      0.0110302000
_diffrn_orient_matrix_UB_21      -0.0748393000
_diffrn_orient_matrix_UB_22      -0.1403276000
_diffrn_orient_matrix_UB_23      -0.0277644000
_diffrn_orient_matrix_UB_31      -0.0076704000
_diffrn_orient_matrix_UB_32      -0.1748760000
_diffrn_orient_matrix_UB_33      0.0294334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.569
_diffrn_reflns_theta_max         66.569
_diffrn_reflns_theta_min         3.784
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0528P)^2^+0.4209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3983
_reflns_number_total             4756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           anxiang_0625
_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_formula_moiety     '2(C17 H16 N2 O)'
_cod_original_formula_sum        'C34 H32 N4 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     528.63
_cod_database_code               7126341
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.81
_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:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C32(H32A,H32B), C30(H30A,
 H30B), C34(H34A,H34B), C36(H36A,H36B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C24(H24), C26(H26), C28(H28), C29(H29),
 C31(H31), C23(H23), C25(H25), C27(H27), C33(H33), C35(H35), C37(H37), C38(H38),
  C39(H39)
;
_shelx_res_checksum              40340
_olex2_date_sample_data_collection 2019-06-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.401
_oxdiff_exptl_absorpt_empirical_full_min 0.837