Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines.
Arachchige, Pandula T Kirinde; Lee, Hanbin; Yi, Chae S.; The Journal of organic chemistry 83 (2018) 4932–4947; doi:10.1021/acs.joc.8b00649

data_4035510
_publ_section_title
;
 Synthesis of Symmetric and Unsymmetric Secondary Amines from the
 Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of
 Primary Amines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4932
_journal_page_last               4947
_journal_paper_doi               10.1021/acs.joc.8b00649
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O4'
_chemical_formula_sum            'C17 H21 N O4'
_chemical_formula_weight         303.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-25
_audit_creation_method
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Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
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_cell_length_c                   12.7605(4)
_cell_measurement_reflns_used    4482
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      74.0290
_cell_measurement_theta_min      3.6360
_cell_volume                     778.11(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987  125.0000   90.0000 94

  2 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987  -99.0000  -60.0000 45

  3 omega  -49.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987   37.0000   60.0000 84

  4 omega    1.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3987  -99.0000   30.0000 82

  5 omega   24.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -94.0000 -120.0000 85

  6 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   30.0000 -150.0000 100

  7 omega   24.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -94.0000 -150.0000 85

  8 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   30.0000  -60.0000 100

  9 omega   94.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  125.0000  120.0000 84

 10 omega   30.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -30.0000   60.0000 60

 11 omega   30.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -77.0000    0.0000 112

 12 omega -120.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987  -77.0000 -180.0000 112

 13 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987  -57.0000  -60.0000 103

 14 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3987  -57.0000   60.0000 103

 15 omega   75.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   77.0000  120.0000 103

 16 omega   78.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   61.0000  -30.0000 100

 17 omega   34.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -45.0000 -150.0000 64

 18 omega   75.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   77.0000 -150.0000 69

 19 omega   47.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   15.0000   90.0000 131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1425597000
_diffrn_orient_matrix_UB_12      0.0363201000
_diffrn_orient_matrix_UB_13      0.0458922000
_diffrn_orient_matrix_UB_21      0.0420987000
_diffrn_orient_matrix_UB_22      0.2005701000
_diffrn_orient_matrix_UB_23      0.0081504000
_diffrn_orient_matrix_UB_31      -0.1170218000
_diffrn_orient_matrix_UB_32      0.0277643000
_diffrn_orient_matrix_UB_33      -0.1185324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8045
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         74.15
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.753
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_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.4341
_exptl_crystal_size_mid          0.0928
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_refine_diff_density_max         0.152
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(14)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2988
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_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0294
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.0867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2825
_reflns_number_total             2988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00649_si_002.cif
_cod_data_source_block           yi3k
_cod_original_cell_volume        778.12(3)
_cod_database_code               4035510
_chemical_oxdiff_formula         'C17 H21 N O4'
_reflns_odcompleteness_completeness 100.00
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_olex2_date_sample_data_collection 2017-01-24
_olex2_date_sample_submission    2017-01-23
_olex2_submission_special_instructions 'No special instructions were received'