Efficient and Selective Synthesis of (E)-Enamides via Ru(II)-Catalyzed Hydroamidation of Internal Alkynes
Kuai, Changsheng; Wang, Lianhui; Cui, Haoyi; Shen, Jinhai; Feng, Yadong; Cui, Xiuling; ACS Catalysis 6 (2016) 186–; doi:10.1021/acscatal.5b01791

data_4513735
_publ_section_title
;
 Efficient and Selective Synthesis of (E)-Enamides via Ru(II)-Catalyzed
 Hydroamidation of Internal Alkynes
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              186
_journal_paper_doi               10.1021/acscatal.5b01791
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C29 H32 N2 O2'
_chemical_formula_sum            'C29 H32 N2 O2'
_chemical_formula_weight         440.56
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-13
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Olex2 1.2
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_cell_measurement_reflns_used    4200
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.3020
_cell_measurement_theta_min      4.7110
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
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  1 omega  -74.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega    1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 27

  3 omega  -72.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 36

  4 omega  -63.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  150.0000 27

  5 omega   67.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 26

  6 omega   70.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -60.0000 26

  7 omega   53.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 72

  8 omega  -13.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -60.0000 99

  9 omega   35.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   90.0000 77

 10 omega   65.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 26

 11 omega   47.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 47

 12 omega  101.00  134.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 33

 13 omega   59.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 49

 14 omega   71.00  133.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 62

 15 omega   61.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 26

 16 omega   51.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 54

 17 omega   44.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 61

 18 omega   43.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 25

 19 omega   92.00  175.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 83

 20 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -180.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1174339000
_diffrn_orient_matrix_UB_12      -0.1161308000
_diffrn_orient_matrix_UB_13      -0.0082390000
_diffrn_orient_matrix_UB_21      0.0694738000
_diffrn_orient_matrix_UB_22      -0.0726854000
_diffrn_orient_matrix_UB_23      0.0419794000
_diffrn_orient_matrix_UB_31      -0.1142222000
_diffrn_orient_matrix_UB_32      0.0752596000
_diffrn_orient_matrix_UB_33      0.0278249000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         4.720
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
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_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description
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_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       0.00265(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0465P)^2^+0.3521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3784
_reflns_number_total             4609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b01791_si_002.cif
_cod_data_source_block           20150462
_cod_depositor_comments          'Adding full bibliography for 4513735.cif.'
_cod_database_code               4513735
_chemical_oxdiff_formula         C20H20N2O2
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.76
_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 Ternary CH refined with riding coordinates:
 C24(H24), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              66440
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'