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_4035307
_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         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-04
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.708(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0848(6)
_cell_length_b                   11.6383(11)
_cell_length_c                   13.0505(10)
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    295.66(10)
_cell_measurement_theta_max      29.0520
_cell_measurement_theta_min      3.4680
_cell_volume                     1227.87(18)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.66(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -3.00   24.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   37.0000 -150.0000 27

  2 omega  -31.00   95.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   19.0000  120.0000 126

  3 omega  -23.00   17.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -99.0000 -150.0000 40

  4 omega -103.00  -78.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803 -178.0000   30.0000 25

  5 omega  -91.00  -58.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803 -178.0000   90.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0104686000
_diffrn_orient_matrix_UB_12      0.0586827000
_diffrn_orient_matrix_UB_13      0.0132088000
_diffrn_orient_matrix_UB_21      0.0431240000
_diffrn_orient_matrix_UB_22      0.0093616000
_diffrn_orient_matrix_UB_23      -0.0462635000
_diffrn_orient_matrix_UB_31      -0.0756745000
_diffrn_orient_matrix_UB_32      0.0134701000
_diffrn_orient_matrix_UB_33      -0.0253335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6864
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1721
_reflns_number_total             2506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01199_si_001.cif
_cod_data_source_block           g170903a
_cod_original_cell_volume        1227.87(17)
_cod_database_code               4035307
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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:
 C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'