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_4035310
_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 O3'
_chemical_formula_sum            'C22 H16 N2 O3'
_chemical_formula_weight         356.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2-alpha
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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  1 omega   -7.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -53.00   49.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega -106.00  -66.00   1.0000   12.0000
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omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -99.0000    0.0000 26
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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'
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'w=1/[\s^2^(Fo^2^)+(0.0268P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
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_olex2_submission_special_instructions 'No special instructions were received'