Cobalt(II)-Catalyzed C-H Amination of Arenes with Simple Alkylamines.
Zhang, Lin-Bao; Zhang, Shou-Kun; Wei, Donghui; Zhu, Xinju; Hao, Xin-Qi; Su, Jian-Hang; Niu, Jun-Long; Song, Mao-Ping; Organic letters 18 (2016) 1318–1321; doi:10.1021/acs.orglett.6b00241

data_1555492
_publ_section_title
;
 Cobalt(II)-Catalyzed C-H Amination of Arenes with Simple Alkylamines.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1318
_journal_page_last               1321
_journal_paper_doi               10.1021/acs.orglett.6b00241
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H17 N3 O3'
_chemical_formula_sum            'C16 H17 N3 O3'
_chemical_formula_weight         299.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-16
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                94.755(5)
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_cell_angle_gamma                102.375(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6512(6)
_cell_length_b                   13.1178(7)
_cell_length_c                   13.2085(9)
_cell_measurement_reflns_used    3704
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.8050
_cell_measurement_theta_min      5.1260
_cell_volume                     1440.34(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_measurement_details
;
  1 omega  -64.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 32

  2 omega   12.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 30

  3 omega  -74.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 31

  4 omega  -24.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -90.0000 27

  5 omega   25.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -90.0000 44

  6 omega   89.00  122.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 33

  7 omega  -12.00   65.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  120.0000 77

  8 omega   96.00  124.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 28

  9 omega  -13.00   65.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -150.0000 78

 10 omega   21.00   70.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 49

 11 omega   39.00   65.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 26

 12 omega   36.00   73.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 37

 13 omega   23.00  113.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 90

 14 omega   66.00  103.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 37

 15 omega   79.00  125.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 46

 16 omega   58.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 50

 17 omega   90.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 25

 18 omega   41.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 56

 19 omega  114.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 51

 20 omega   52.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 25

 21 omega   40.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 63

 22 omega   53.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 36

 23 omega   44.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 46

 24 omega   61.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 72

 25 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 26

 26 omega   44.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 54

 27 omega   59.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 28

 28 omega   47.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 27

 29 omega  127.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 42

 30 omega  116.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 49

 31 omega   42.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 55

 32 omega   67.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 41

 33 omega   73.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -150.0000 105

 34 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   90.0000 46

 35 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 90

 36 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  150.0000 90

 37 omega   35.00   89.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -120.0000 54

 38 omega   35.00  125.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0851768000
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_diffrn_orient_matrix_UB_13      0.0886691000
_diffrn_orient_matrix_UB_21      0.1545705000
_diffrn_orient_matrix_UB_22      0.0094536000
_diffrn_orient_matrix_UB_23      0.0770866000
_diffrn_orient_matrix_UB_31      0.0543613000
_diffrn_orient_matrix_UB_32      0.1165068000
_diffrn_orient_matrix_UB_33      -0.0158869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10373
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.088
_diffrn_reflns_theta_max         67.088
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90510
_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_density_diffrn    1.380
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0065(4)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0637P)^2^+0.1349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4055
_reflns_number_total             5144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00241_si_002.cif
_cod_data_source_block           3aa
_cod_original_cell_volume        1440.35(16)
_cod_database_code               1555492
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.98
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13C,H13D), C14(H14C,H14D), C15(H15C,H15D), C16(H16C,H16D), C13'(H13A,
 H13B), C14'(H14A,H14B), C15'(H15A,H15B), C16'(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), N1(H1),
 C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12'), N1'(H1')
;
_shelx_res_checksum              17733
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'