Carboxylate Ligand-Exchanged Amination/C(sp3)–H Arylation Reaction via Pd/Norbornene Cooperative Catalysis
Zhang, Bo-Sheng; Li, Yuke; An, Yang; Zhang, Zhe; Liu, Ce; Wang, Xin-Gang; Liang, Yong-Min; ACS Catalysis 8 (2018) 11827–; doi:10.1021/acscatal.8b04163

data_4515771
_publ_section_title
;
 Carboxylate Ligand-Exchanged Amination/C(sp3)--H Arylation Reaction via
 Pd/Norbornene Cooperative Catalysis
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              11827
_journal_paper_doi               10.1021/acscatal.8b04163
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C18 H26 N2 O3'
_chemical_formula_sum            'C18 H26 N2 O3'
_chemical_formula_weight         318.41
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.380(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2992(11)
_cell_length_b                   15.1980(11)
_cell_length_c                   12.6751(8)
_cell_measurement_reflns_used    1387
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9690
_cell_measurement_theta_min      3.8690
_cell_volume                     1767.4(3)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -19.00   14.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000  120.0000 22

  2 omega  -16.00   20.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000  -30.0000 24

  3 omega   51.00   78.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430 -178.0000  -90.0000 18

  4 omega   -7.00   66.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -99.0000 -120.0000 49

  5 omega    7.00   82.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430   38.0000    0.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0701751000
_diffrn_orient_matrix_UB_12      -0.0133267000
_diffrn_orient_matrix_UB_13      0.0255998000
_diffrn_orient_matrix_UB_21      -0.0093619000
_diffrn_orient_matrix_UB_22      -0.0410177000
_diffrn_orient_matrix_UB_23      -0.0268862000
_diffrn_orient_matrix_UB_31      0.0310858000
_diffrn_orient_matrix_UB_32      0.0177997000
_diffrn_orient_matrix_UB_33      -0.0428908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6801
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69663
_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    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.1545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1775
_reflns_number_gt                2133
_reflns_number_total             3477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs8b04163_si_002.cif
_cod_data_source_block           zhangbsh_0903
_cod_database_code               4515771
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C18(H18a,H18b), C19(H19a,H19b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C17(H17)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C22(H22a,H22b,H22c), C23(H23a,H23b,
 H23c)
;
_olex2_date_sample_data_collection 2018-09-04
_olex2_submission_special_instructions 'No special instructions were received'