#------------------------------------------------------------------------------
#$Date: 2022-09-14 20:32:59 +0200 (Wed 14 de Sep de 2022) $
#$Revision: 277840 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/19/4021992.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021992
loop_
_publ_author_name
'Maike V. Peters'
'Ragnar S. Stoll'
'Richard Goddard'
'Gernot Buth'
'Stefan Hecht'
_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 φ- and ω-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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0861P)²+0.0000P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2382(2) 0.7874(5) 0.1005(7) 0.0481(15) Uani 1 1 d .
C2 C 0.1801(2) 0.8319(4) 0.0762(7) 0.0438(14) Uani 1 1 d .
C3 C 0.1254(2) 0.7837(4) 0.0992(7) 0.0500(15) Uani 1 1 d .
H3 H 0.1216 0.7095 0.1353 0.060 Uiso 1 1 calc R
C4 C 0.0777(3) 0.8484(4) 0.0672(7) 0.0531(16) Uani 1 1 d .
H4 H 0.0410 0.8184 0.0837 0.064 Uiso 1 1 calc R
C5 C 0.0838(2) 0.9586(4) 0.0102(7) 0.0517(15) Uani 1 1 d .
H5 H 0.0508 1.0010 -0.0115 0.062 Uiso 1 1 calc R
C6 C 0.1370(2) 1.0068(4) -0.0150(7) 0.0525(15) Uani 1 1 d .
H6 H 0.1407 1.0805 -0.0543 0.063 Uiso 1 1 calc R
C7 C 0.1848(2) 0.9413(4) 0.0204(7) 0.0447(14) Uani 1 1 d .
C8 C 0.3351(2) 0.8741(4) 0.0362(7) 0.0436(14) Uani 1 1 d .
C9 C 0.3680(2) 0.7914(4) 0.1172(7) 0.0488(15) Uani 1 1 d .
H9 H 0.3508 0.7374 0.1927 0.059 Uiso 1 1 calc R
C10 C 0.4269(2) 0.7896(4) 0.0848(7) 0.0495(15) Uani 1 1 d .
H10 H 0.4491 0.7326 0.1361 0.059 Uiso 1 1 calc R
C11 C 0.4533(2) 0.8711(4) -0.0225(7) 0.0529(16) Uani 1 1 d .
H11 H 0.4929 0.8691 -0.0441 0.063 Uiso 1 1 calc R
C12 C 0.4198(3) 0.9557(4) -0.0972(7) 0.0493(15) Uani 1 1 d .
H12 H 0.4373 1.0120 -0.1670 0.059 Uiso 1 1 calc R
C13 C 0.3602(2) 0.9578(4) -0.0695(7) 0.0472(15) Uani 1 1 d .
H13 H 0.3378 1.0144 -0.1212 0.057 Uiso 1 1 calc R
N1 N 0.2741(2) 0.8767(3) 0.0668(5) 0.0443(12) Uani 1 1 d .
N2 N 0.24339(19) 0.9702(4) 0.0018(6) 0.0489(13) Uani 1 1 d .
H1 H 0.2532(18) 1.035(4) 0.056(6) 0.040(15) Uiso 1 1 d .
O1 O 0.25408(15) 0.6912(3) 0.1399(5) 0.0516(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.066(5) 0.044(4) 0.035(4) -0.001(3) 0.000(3) -0.009(3)
C2 0.047(4) 0.042(3) 0.043(4) -0.002(3) -0.003(3) 0.003(3)
C3 0.068(4) 0.038(3) 0.045(4) -0.002(2) 0.000(3) -0.003(3)
C4 0.053(4) 0.054(4) 0.053(4) -0.003(3) 0.003(3) -0.003(3)
C5 0.051(4) 0.051(4) 0.053(4) 0.001(3) -0.002(3) 0.004(3)
C6 0.065(4) 0.047(3) 0.045(4) 0.002(3) 0.001(3) 0.002(3)
C7 0.048(4) 0.048(3) 0.038(3) -0.003(3) -0.001(3) -0.003(3)
C8 0.052(4) 0.043(3) 0.036(3) -0.004(3) 0.000(3) 0.002(3)
C9 0.055(4) 0.044(3) 0.047(4) -0.002(3) 0.002(3) 0.000(3)
C10 0.058(4) 0.043(3) 0.047(4) 0.000(3) -0.002(3) 0.003(3)
C11 0.055(4) 0.058(4) 0.046(4) -0.008(3) 0.002(3) -0.002(3)
C12 0.056(4) 0.048(3) 0.043(4) 0.000(3) 0.003(3) -0.010(3)
C13 0.062(4) 0.042(3) 0.037(4) 0.002(3) -0.003(3) -0.002(3)
N1 0.056(3) 0.031(2) 0.045(3) 0.0015(19) 0.000(2) 0.003(2)
N2 0.059(4) 0.033(3) 0.055(3) 0.000(2) -0.002(3) 0.004(2)
O1 0.064(3) 0.036(2) 0.054(2) 0.0025(17) 0.001(2) -0.0002(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 125.7(5) y
O1 C1 C2 129.8(5) y
N1 C1 C2 104.5(5) y
C7 C2 C3 119.9(5) y
C7 C2 C1 108.1(5) y
C3 C2 C1 132.0(5) y
C4 C3 C2 118.5(5) y
C4 C3 H3 120.8 n
C2 C3 H3 120.8 n
C3 C4 C5 120.4(5) y
C3 C4 H4 119.8 n
C5 C4 H4 119.8 n
C6 C5 C4 122.0(5) y
C6 C5 H5 119.0 n
C4 C5 H5 119.0 n
C5 C6 C7 117.1(5) y
C5 C6 H6 121.4 n
C7 C6 H6 121.4 n
C2 C7 C6 122.2(5) y
C2 C7 N2 109.7(5) y
C6 C7 N2 128.1(5) y
C9 C8 C13 121.2(6) y
C9 C8 N1 119.9(5) y
C13 C8 N1 118.8(5) y
C8 C9 C10 119.2(5) y
C8 C9 H9 120.4 n
C10 C9 H9 120.4 n
C11 C10 C9 121.1(5) y
C11 C10 H10 119.4 n
C9 C10 H10 119.4 n
C10 C11 C12 118.8(5) y
C10 C11 H11 120.6 n
C12 C11 H11 120.6 n
C11 C12 C13 121.0(5) y
C11 C12 H12 119.5 n
C13 C12 H12 119.5 n
C8 C13 C12 118.6(5) y
C8 C13 H13 120.7 n
C12 C13 H13 120.7 n
C1 N1 N2 111.9(5) y
C1 N1 C8 127.3(4) y
N2 N1 C8 117.9(4) y
N1 N2 C7 105.1(4) y
N1 N2 H1 115(3) y
C7 N2 H1 115(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.242(5) y
C1 N1 1.377(6) y
C1 C2 1.457(7) y
C2 C7 1.376(7) y
C2 C3 1.402(7) y
C3 C4 1.369(7) y
C3 H3 0.9300 n
C4 C5 1.390(7) y
C4 H4 0.9300 n
C5 C6 1.372(6) y
C5 H5 0.9300 n
C6 C7 1.380(6) y
C6 H6 0.9300 n
C7 N2 1.407(6) y
C8 C9 1.376(6) y
C8 C13 1.381(6) y
C8 N1 1.430(6) y
C9 C10 1.383(7) y
C9 H9 0.9300 n
C10 C11 1.382(7) y
C10 H10 0.9300 n
C11 C12 1.384(7) y
C11 H11 0.9300 n
C12 C13 1.394(7) y
C12 H12 0.9300 n
C13 H13 0.9300 n
N1 N2 1.405(5) y
N2 H1 0.90(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 364308
