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_7053147
_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             2013-03-26
_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                 99.558(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0325(6)
_cell_length_b                   15.3958(15)
_cell_length_c                   6.1563(3)
_cell_measurement_reflns_used    2950
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      70.6813
_cell_measurement_theta_min      3.4362
_cell_volume                     1218.09(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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      293.0(2)
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
1 omega -40.00 28.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 -150.0000 68

2 omega -80.00 37.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 19.0000 -30.0000 117

3 omega -49.00 29.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 30.0000 78

4 omega 22.00 99.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -125.0000 150.0000 77

5 omega 32.00 85.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -90.0000 53

6 omega 40.00 174.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 15.0000 -90.0000 134

7 omega 35.00 68.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -180.0000 33

8 omega 49.00 75.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -77.0000 -90.0000 26

9 omega 36.00 109.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 -150.0000 73

10 omega 38.00 104.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -61.0000 0.0000 66

11 omega 123.00 175.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 -90.0000 52

12 omega 70.00 154.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 61.0000 -60.0000 84

13 omega 60.00 103.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -90.0000 43

14 omega 30.00 87.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 30.0000 57

15 omega 23.00 100.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 -30.0000 77

16 omega 23.00 75.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -30.0000 52

17 omega 124.00 150.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -90.0000 26

18 omega 50.00 76.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 0.0000 26

19 omega 83.00 109.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 0.0000 26

20 omega 114.00 174.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 133.0000 42.0000 60

21 omega 148.00 173.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 -120.0000 25

22 omega 83.00 113.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -111.0000 120.0000 30

23 omega -120.00 -8.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -90.0000 112

24 omega -116.00 -12.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -57.0000 150.0000 104

25 omega -120.00 -8.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -30.0000 112

26 omega -116.00 -12.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -57.0000 30.0000 104

27 omega 69.00 178.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 30.0000 90.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0005654000
_diffrn_orient_matrix_UB_12      -0.0989962000
_diffrn_orient_matrix_UB_13      0.0368150000
_diffrn_orient_matrix_UB_21      0.0392575000
_diffrn_orient_matrix_UB_22      0.0139924000
_diffrn_orient_matrix_UB_23      0.2474964000
_diffrn_orient_matrix_UB_31      -0.1133274000
_diffrn_orient_matrix_UB_32      0.0043901000
_diffrn_orient_matrix_UB_33      0.0413123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13222
_diffrn_reflns_theta_full        70.81
_diffrn_reflns_theta_max         70.81
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0539P)^2^+0.1111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                1644
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00186e.cif
_cod_data_source_block           5_293K_new
_cod_original_cell_volume        1218.09(14)
_cod_database_code               7053147
_chemical_oxdiff_formula         'C13 H8 N4 O2'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13