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_1517252
_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 H18 Cl N O2'
_chemical_formula_sum            'C19 H18 Cl N O2'
_chemical_formula_weight         327.81
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4739(8)
_cell_length_b                   14.9845(9)
_cell_length_c                   10.5112(9)
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_cell_measurement_temperature    298
_cell_measurement_theta_max      63.1980
_cell_measurement_theta_min      5.1530
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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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)
;
_computing_data_reduction
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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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_diffrn_measurement_details
;
  1 omega   32.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   49.00   81.00   1.0000    1.0000
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  3 omega -123.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -48.6750  -37.0000 -120.0000 103

  4 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.6750  125.0000 -180.0000 25

  5 omega   73.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.6750  125.0000 -120.0000 44

  6 omega   19.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000   90.0000 27

  7 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000 -180.0000 26

  8 omega   20.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -37.0000  -30.0000 43

  9 omega   18.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -25.0000  120.0000 46

 10 omega   36.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -50.0000 -150.0000 36

 11 omega   19.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000  -30.0000 53

 12 omega   42.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  179.0000 -120.0000 69

 13 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500   12.0000 -120.0000 25

 14 omega  103.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500   12.0000 -120.0000 25

 15 omega  140.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500   12.0000 -120.0000 38

 16 omega   33.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -37.0000  -90.0000 38

 17 omega   38.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000  -90.0000 39

 18 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000   90.0000 25

 19 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  179.0000  150.0000 25

 20 omega -108.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -48.6750  125.0000   30.0000 83

 21 omega   95.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.6750  125.0000    0.0000 26

 22 omega   98.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.6750  125.0000  -90.0000 26

 23 omega -166.00 -140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -92.0000 -158.0000   19.0000 26

 24 omega -140.00 -114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -92.0000  -91.0000 -120.0000 26

 25 omega   91.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -63.0000   60.0000 26

 26 omega   72.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -91.0000 -150.0000 48

 27 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  179.0000   30.0000 26

 28 omega   43.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -63.0000   60.0000 31

 29 omega   45.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -91.0000 -150.0000 26

 30 omega   77.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -91.0000  150.0000 46

 31 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  111.0000   30.0000 26

 32 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -63.0000  150.0000 26

 33 omega   19.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000   60.0000 49

 34 omega   37.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -91.0000  150.0000 25

 35 omega   36.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000 -120.0000 28

 36 omega  -20.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 26

 37 omega   79.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.6750  125.0000 -180.0000 33

 38 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -50.0000 -150.0000 25

 39 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -25.0000  -30.0000 26

 40 omega   45.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500 -111.0000  -60.0000 26

 41 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3500  -37.0000  120.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0184597000
_diffrn_orient_matrix_UB_12      -0.0275975000
_diffrn_orient_matrix_UB_13      -0.1377531000
_diffrn_orient_matrix_UB_21      0.1235803000
_diffrn_orient_matrix_UB_22      0.0564326000
_diffrn_orient_matrix_UB_23      0.0083052000
_diffrn_orient_matrix_UB_31      0.0795480000
_diffrn_orient_matrix_UB_32      -0.0814892000
_diffrn_orient_matrix_UB_33      0.0523171000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7962
_diffrn_reflns_theta_full        63.3319
_diffrn_reflns_theta_max         63.33
_diffrn_reflns_theta_min         5.17
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3296
_exptl_crystal_description       block
_exptl_crystal_F_000             691.4048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3017
_refine_diff_density_min         -0.5870
_refine_diff_density_rms         0.1151
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_refine_ls_d_res_low             8.5624
_refine_ls_goodness_of_fit_ref   1.0632
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
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_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0632
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.0907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -7
_reflns_number_gt                2097
_reflns_number_total             2527
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            pClCu.cif
_cod_data_source_block           pClCu-red
_cod_depositor_comments
'Adding full bibliography for 1517251--1517252.cif.'
_cod_database_code               1517252
_chemical_oxdiff_formula         'C H O Cl'
_reflns_odcompleteness_completeness 94.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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:
 C12(H12a,H12b), C15(H15a,H15b), C20(H20a,H20b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14), C16(H16), C18(H18),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;