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_4021990
_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        'pentane also hexane/diethylether'
_chemical_formula_moiety         'C23 H24 N4'
_chemical_formula_sum            'C23 H24 N4'
_chemical_formula_weight         356.46
_chemical_name_systematic
; 
 4-tert-butyl-3,5-bis(phenyldiazenyl)toluene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 104.029(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   17.081(4)
_cell_length_b                   6.1806(17)
_cell_length_c                   18.749(5)
_cell_measurement_reflns_used    974
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.452
_cell_measurement_theta_min      3.699
_cell_volume                     1920.3(9)
_computing_cell_refinement       'SMART software (Bruker AXS, 2003)'
_computing_data_collection       'SMART software (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT software (v6.45A, Bruker AXS)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS APEX'
_diffrn_measurement_method       'CCD \w-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'PX beamline, ANKA'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80000
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19640
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.768049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10, Bruker AXS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+4.3472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                3121
_reflns_number_total             3948
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo061288zsi20060622_090245.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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021990