Acid-Promoted Bicyclization of Diaryl Alkynes: Synthesis of 2 H-Indazoles with in Situ Generated Diazonium Salt as Nitrogen Source.
Zhang, Cheng; Chang, Sailan; Dong, Shanliang; Qiu, Lihua; Xu, Xinfang; The Journal of organic chemistry 83 (2018) 9125–9136; doi:10.1021/acs.joc.8b01199

data_4035308
_publ_section_title
;
 Acid-Promoted Bicyclization of Diaryl Alkynes: Synthesis of 2 H-Indazoles
 with in Situ Generated Diazonium Salt as Nitrogen Source.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9125
_journal_page_last               9136
_journal_paper_doi               10.1021/acs.joc.8b01199
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2-alpha
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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  1 omega    1.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   12.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   43.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.3991 -178.0000   60.0000 39

  4 omega  -22.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -57.0000 -150.0000 30

  5 omega    3.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803   37.0000 -120.0000 26

  6 omega   -5.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega  -76.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   35.00   60.00   1.0000    5.0000
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_diffrn_reflns_number            12225
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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;
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'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^] 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, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
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2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
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