Metal-free visible-light induced cross-dehydrogenative coupling of tertiary amines with diazo compounds.
Xiao, Tiebo; Li, Linyong; Lin, Guoliang; Mao, Zong-Wan; Zhou, Lei; Organic letters 16 (2014) 4232–4235; doi:10.1021/ol501933h

data_1517251
_publ_section_title
;
 Metal-free visible-light induced cross-dehydrogenative coupling of
 tertiary amines with diazo compounds.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4232
_journal_page_last               4235
_journal_paper_doi               10.1021/ol501933h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.37
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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;
  1 omega -102.00  -64.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
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  2 omega  -37.00  -11.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
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  3 omega   33.00   59.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.3979  -37.0000  -60.0000 26

  4 omega   63.00  110.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.3979  179.0000  -60.0000 47

  5 omega   10.00  102.00   1.0000    3.0900
omega____ theta____ kappa____ phi______ frames
    -       34.3979   37.0000  120.0000 92

  6 omega   18.00   66.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000   30.0000 48

  7 omega   19.00   69.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000  -90.0000 50

  8 omega   22.00   47.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000 -150.0000 25

  9 omega  133.00  158.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000  -90.0000 25

 10 omega   36.00   75.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -45.0000  -30.0000 39

 11 omega   21.00   54.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -94.0000 -180.0000 33

 12 omega   20.00   64.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000 -180.0000 44

 13 omega   70.00  106.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000  -90.0000 36

 14 omega  120.00  152.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500   45.0000   90.0000 32

 15 omega   68.00   93.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500   45.0000   90.0000 25

 16 omega   86.00  112.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000 -180.0000 26

 17 omega   24.00   52.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000   30.0000 28

 18 omega   64.00  112.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000  120.0000 48

 19 omega   26.00   71.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -94.0000   30.0000 45

 20 omega   24.00   74.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000  120.0000 50

 21 omega   24.00   49.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -77.0000  -30.0000 25

 22 omega   85.00  110.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -77.0000  -30.0000 25

 23 omega   32.00   75.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -94.0000  150.0000 43

 24 omega  110.00  155.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000 -180.0000 45

 25 omega   97.00  129.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000  -30.0000 32

 26 omega   72.00  122.00   1.0000   12.3600
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -89.0000  153.5355 50
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
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_diffrn_orient_matrix_UB_32      -0.0705006000
_diffrn_orient_matrix_UB_33      -0.0837878000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
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_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
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_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_process_details
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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.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_density_diffrn    1.2654
_exptl_crystal_description       block
_exptl_crystal_F_000             625.9190
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.0733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            IndoN2.cif
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_cod_depositor_comments
'Adding full bibliography for 1517251--1517252.cif.'
_cod_original_cell_volume        1539.78(19)
_cod_database_code               1517251
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 97.24
_reflns_odcompleteness_iscentric 1
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_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:
 C10(H10a,H10b), C15(H15a,H15b), C22(H22a,H22b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c)
;