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_4035309
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
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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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CrysAlisPro, Agilent Technologies,
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  1 omega   -8.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   42.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  4 omega  -32.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega  -23.00   26.00   1.0000   20.0000
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omega____ theta____ kappa____ phi______ frames
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
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_diffrn_source                   'Enhance (Mo) X-ray Source'
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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 white'
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'w=1/[\s^2^(Fo^2^)+(0.0512P)^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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
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_olex2_submission_special_instructions 'No special instructions were received'