Palladium-Catalyzed Selective β-Arylation of Aliphatic Amides Using a Removable N,O-Bidentate Auxiliary
Zhang, Shou-Kun; Yang, Xin-Yan; Zhao, Xue-Mei; Li, Peng-Xiang; Niu, Jun-Long; Song, Mao-Ping; Organometallics 34 (2015) 4331–; doi:10.1021/acs.organomet.5b00581

data_4087761
_publ_section_title
;
 Palladium-Catalyzed Selective \b-Arylation of Aliphatic Amides Using a
 Removable N,O-Bidentate Auxiliary
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4331
_journal_paper_doi               10.1021/acs.organomet.5b00581
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-06
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.504(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7515(8)
_cell_length_b                   4.7970(3)
_cell_length_c                   18.4272(12)
_cell_measurement_reflns_used    1203
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.2981
_cell_measurement_theta_min      3.0692
_cell_volume                     1209.96(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -1.00   25.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000 -180.0000 26

  2 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8666   37.0000   30.0000 92

  3 omega   -6.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8666   37.0000  120.0000 91

  4 omega  -49.00  -12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8666  -57.0000  -30.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0367595000
_diffrn_orient_matrix_UB_12      0.0204800000
_diffrn_orient_matrix_UB_13      -0.0239739000
_diffrn_orient_matrix_UB_21      -0.0357349000
_diffrn_orient_matrix_UB_22      -0.0104338000
_diffrn_orient_matrix_UB_23      -0.0303023000
_diffrn_orient_matrix_UB_31      -0.0076580000
_diffrn_orient_matrix_UB_32      0.1460762000
_diffrn_orient_matrix_UB_33      0.0011580000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5203
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.355
_diffrn_reflns_theta_min         3.517
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description
;
;
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0671
_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^)+(0.0453P)^2^+0.1077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1745
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00581_si_002.cif
_cod_data_source_block           complex-3aa
_cod_original_cell_volume        1209.96(14)
_cod_database_code               4087761
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.71
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_shelx_res_checksum              4986
_shelx_hkl_checksum              65579
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'