The reaction of NH-indazoles with 1-fluoro-2,4-dinitrobenzene: the unusual formation of benzotriazole-N-oxides
Alkorta, Ibon; Cossío, Fernando P.; Elguero, José; Fresno, Nieves; Hernandez-Folgado, Laura; García-Granda, Santiago; Menéndez-Taboada, Laura; Pérez-Fernández, Ruth; Reviriego, Felipe; Vázquez-Viñuela, Lucia; New Journal of Chemistry 37 (2013) 2384–; doi:10.1039/c3nj00186e

data_7053146
_publ_section_title
;
 The reaction of NH-indazoles with 1-fluoro-2,4-dinitrobenzene: the
 unusual formation of benzotriazole-N-oxides
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2384
_journal_paper_doi               10.1039/c3nj00186e
_journal_volume                  37
_journal_year                    2013
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-07
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2013-04-08 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.334(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2107(6)
_cell_length_b                   24.0635(17)
_cell_length_c                   14.4077(11)
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.5781
_cell_measurement_theta_min      3.6161
_cell_volume                     2459.4(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
1 omega -68.00 29.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 -90.0000 97

2 omega 48.00 99.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -125.0000 30.0000 51

3 omega -24.00 11.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -37.0000 30.0000 35

4 omega 72.00 173.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 45.0000 30.0000 101

5 omega 99.00 125.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 150.0000 26

6 omega 140.00 169.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 150.0000 29

7 omega 91.00 117.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 60.0000 26

8 omega 90.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 90.0000 38

9 omega 94.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 -150.0000 34

10 omega 17.00 107.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -97.0000 -39.0000 90

11 omega 96.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 -60.0000 32

12 omega 95.00 120.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0860319000
_diffrn_orient_matrix_UB_12      -0.0583816000
_diffrn_orient_matrix_UB_13      0.0031763000
_diffrn_orient_matrix_UB_21      -0.0680906000
_diffrn_orient_matrix_UB_22      0.0153492000
_diffrn_orient_matrix_UB_23      0.0921980000
_diffrn_orient_matrix_UB_31      -0.1872563000
_diffrn_orient_matrix_UB_32      0.0213073000
_diffrn_orient_matrix_UB_33      -0.0576293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8843
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2843
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.0135
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0385P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1709
_reflns_number_gt                2303
_reflns_number_total             4556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00186e.cif
_cod_data_source_block           4_293K_new
_cod_original_cell_volume        2459.4(3)
_cod_database_code               7053146
_chemical_oxdiff_formula         'C13 H8 N4 O4'
_reflns_odcompleteness_completeness 98.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49