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_7053144
_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_absolute_configuration unk
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-03
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0459(2)
_cell_length_b                   11.048(3)
_cell_length_c                   15.4564(4)
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.2804
_cell_measurement_theta_min      3.9981
_cell_volume                     1203.2(3)
_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      120.15
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
1 omega -96.00 -28.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -37.0000 30.0000 68

2 omega -96.00 -12.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 125.0000 -180.0000 84

3 omega 99.00 126.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 150.0000 27

4 omega 73.00 108.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 76.0000 -117.0000 35

5 omega 136.00 167.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 76.0000 -117.0000 31

6 omega 28.00 114.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -75.0000 52.0000 86

7 omega 110.00 177.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 60.0000 67

8 omega 76.00 167.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 45.0000 -120.0000 91

9 omega 94.00 120.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 60.0000 26

10 omega 113.00 177.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 0.0000 64

11 omega -120.00 -95.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1816885000
_diffrn_orient_matrix_UB_12      0.0589204000
_diffrn_orient_matrix_UB_13      0.0362603000
_diffrn_orient_matrix_UB_21      -0.0039548000
_diffrn_orient_matrix_UB_22      -0.0939678000
_diffrn_orient_matrix_UB_23      0.0736830000
_diffrn_orient_matrix_UB_31      0.1215767000
_diffrn_orient_matrix_UB_32      0.0845444000
_diffrn_orient_matrix_UB_33      0.0564648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.41
_diffrn_reflns_theta_min         4.92
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.912
_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_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1436
_exptl_crystal_size_mid          0.0829
_exptl_crystal_size_min          0.0622
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0365P)^2^+0.0293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                2051
_reflns_number_total             2258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00186e.cif
_cod_data_source_block           3_120K_new
_cod_original_cell_volume        1203.1(3)
_cod_database_code               7053144
_chemical_oxdiff_formula         'C13 H8 N4 O4 '
_chemical_oxdiff_usercomment     'Medida a RT - GMN10040'
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     68.13