Rhodium/Copper Cocatalyzed Highly trans-Selective 1,2-Diheteroarylation of Alkynes with Azoles via C-H Addition/Oxidative Cross-Coupling: A Combined Experimental and Theoretical Study.
Tan, Guangying; Zhu, Lei; Liao, Xingrong; Lan, Yu; You, Jingsong; Journal of the American Chemical Society 139 (2017) 15724–15737; doi:10.1021/jacs.7b07242

data_4131593
_publ_section_title
;
 Rhodium/Copper Cocatalyzed Highly trans-Selective 1,2-Diheteroarylation
 of Alkynes with Azoles via C-H Addition/Oxidative Cross-Coupling: A
 Combined Experimental and Theoretical Study.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15724
_journal_page_last               15737
_journal_paper_doi               10.1021/jacs.7b07242
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-03
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Olex2 1.2
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_computing_cell_refinement
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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)
;
_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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;
  1 omega   23.00   90.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
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  2 omega   10.00  104.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

  3 omega  -33.00   55.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

  4 omega  -31.00   53.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -150.0000 84

  5 omega  -31.00   63.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -60.0000 94

  6 omega    7.00  108.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000 -150.0000 101

  7 omega  -31.00   63.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  8 omega    1.00   75.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  9 omega   23.00   90.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

 10 omega   39.00  109.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
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 11 omega   38.00   91.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
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 12 omega   39.00  109.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 13 omega   40.00   98.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 14 omega   82.00  178.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   24.0000  114.1466 96

 15 omega   38.00   91.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 16 omega   38.00   91.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 17 omega   91.00  176.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 18 omega   39.00  109.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 19 omega   38.00   91.00   1.0000    6.3900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53
;
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_diffrn_orient_matrix_UB_11      0.0379335000
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_diffrn_orient_matrix_UB_21      0.1325147000
_diffrn_orient_matrix_UB_22      0.0359265000
_diffrn_orient_matrix_UB_23      0.0318038000
_diffrn_orient_matrix_UB_31      0.0143327000
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_diffrn_orient_matrix_UB_33      0.0104492000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_unetI/netI     0.0241
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_diffrn_reflns_theta_min         6.142
_diffrn_source                   'Enhance (Cu) X-ray Source'
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_description       plate
_exptl_crystal_F_000             624
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_exptl_crystal_size_mid          0.45
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+0.1330P] where P=(Fo^2^+2Fc^2^)/3'
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
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_shelx_hkl_checksum              88089
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_olex2_date_sample_data_collection 2017-01-03
_olex2_submission_special_instructions 'No special instructions were received'