Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.
Zhu, Jie S.; Li, Clarabella J.; Tsui, Ka Yi; Kraemer, Niklas; Son, Jung-Ho; Haddadin, Makhluf J.; Tantillo, Dean J.; Kurth, Mark J.; Journal of the American Chemical Society 141 (2019) 6247–6253; doi:10.1021/jacs.8b13481

data_4128674
_publ_section_title
;
 Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for
 the Cadogan and Davis-Beirut Reactions.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6247
_journal_page_last               6253
_journal_paper_doi               10.1021/jacs.8b13481
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C10 H12 N2 O'
_chemical_formula_weight         176.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 106.537(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1799(9)
_cell_length_b                   8.3702(13)
_cell_length_c                   9.1069(14)
_cell_measurement_reflns_used    4072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.33
_cell_volume                     451.59(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4113
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.417
_diffrn_reflns_theta_min         2.333
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.180
_refine_ls_abs_structure_details
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.262
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.261
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                1761
_reflns_number_total             1770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13481_si_004.cif
_cod_data_source_block           n-isopropyl-n-oxide
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128674
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              70377
_shelx_hkl_checksum              96784