On the Illusive Nature of o-Formylazobenzenes: Exploiting the Nucleophilicity of the Azo Group for Cyclization to Indazole Derivatives
Maike V. Peters; Ragnar S. Stoll; Richard Goddard; Gernot Buth; Stefan Hecht; Journal of Organic Chemistry 71 (2006) 7840–7845; doi:10.1021/jo061288z

data_4021992
_publ_section_title
;
 On the Illusive Nature of o-Formylazobenzenes: Exploiting the
 Nucleophilicity of the Azo Group for Cyclization to Indazole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7840
_journal_page_last               7845
_journal_paper_doi               10.1021/jo061288z
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        acetonitrile
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_chemical_name_systematic
; 
 2-N-phenyl-indazol-3-one
;
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   23.155(2)
_cell_length_b                   11.9939(13)
_cell_length_c                   7.0969(7)
_cell_measurement_reflns_used    435
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.19
_cell_measurement_theta_min      3.82
_cell_volume                     1970.9(3)
_computing_cell_refinement       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2075
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            18525
_diffrn_reflns_theta_full        53.90
_diffrn_reflns_theta_max         53.90
_diffrn_reflns_theta_min         3.82
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.731192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                662
_reflns_number_total             1182
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo061288zsi20060622_090322.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4021992