Iron promoted C3-H nitration of 2H-indazole: direct access to 3-nitro-2H-indazoles.
Murugan, Arumugavel; Gorantla, Koteswar Rao; Mallik, Bhabani S.; Sharada, Duddu S.; Organic & biomolecular chemistry 16 (2018) 5113–5118; doi:10.1039/c8ob00931g

data_7156307
_publ_section_title
;
 Iron promoted C3-H nitration of 2H-indazole: direct access to
 3-nitro-2H-indazoles.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5113
_journal_page_last               5118
_journal_paper_doi               10.1039/c8ob00931g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C15 H11 N3 O3'
_chemical_formula_sum            'C15 H11 N3 O3'
_chemical_formula_weight         281.27
_chemical_melting_point          443.15
_chemical_name_systematic        1-(3-(3-nitro-2H-indazol-2-yl)phenyl)ethanone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-23 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                91.064(17)
_cell_angle_beta                 108.89(2)
_cell_angle_gamma                113.92(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8053(18)
_cell_length_b                   8.2606(17)
_cell_length_c                   11.869(2)
_cell_measurement_reflns_used    916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9384
_cell_measurement_theta_min      2.9446
_cell_volume                     651.9(3)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
  1 omega  -82.00   11.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -77.0000    0.0000 93

  2 omega  -86.00  -55.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -77.0000  -30.0000 31

  3 omega   -4.00   23.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -      -18.3513  -99.0000 -150.0000 27

  4 omega  -48.00   40.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  -57.0000   90.0000 88

  5 omega    7.00   62.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263   57.0000 -150.0000 55

  6 omega   70.00   98.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  178.0000    0.0000 28

  7 omega   30.00   89.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263   57.0000 -120.0000 59

  8 omega  -52.00   19.00   1.0000   21.3500
omega____ theta____ kappa____ phi______ frames
    -       20.2263  -38.0000 -120.0000 71
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0878554000
_diffrn_orient_matrix_UB_12      0.0809461000
_diffrn_orient_matrix_UB_13      0.0102562000
_diffrn_orient_matrix_UB_21      0.0332397000
_diffrn_orient_matrix_UB_22      -0.0442613000
_diffrn_orient_matrix_UB_23      -0.0340362000
_diffrn_orient_matrix_UB_31      -0.0506083000
_diffrn_orient_matrix_UB_32      0.0240199000
_diffrn_orient_matrix_UB_33      -0.0533940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5672
_diffrn_reflns_theta_full        29.0056
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            Yellow
_exptl_crystal_density_diffrn    1.4329
_exptl_crystal_description       irregular
_exptl_crystal_F_000             292.1382
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.4258
_refine_diff_density_min         -0.4612
_refine_diff_density_rms         0.1180
_refine_ls_d_res_high            0.7329
_refine_ls_d_res_low             6.9117
_refine_ls_goodness_of_fit_ref   1.0545
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0545
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0344P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1505
_reflns_number_total             2992
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob00931g2.cif
_cod_data_source_block           exp_7218
_cod_depositor_comments          'Adding full bibliography for 7156307.cif.'
_cod_database_code               7156307
_chemical_oxdiff_formula         'C23 H14 N2 O2'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1AA(0.053) H9(0.048) H13(0.054) H11(0.058) H3(0.057) H12(0.061)
 H6(0.062) H5(0.067) H15a(0.1) H15b(0.1) H15c(0.1) H4(0.067)
 Fixed X: H1AA(0.9446) H9(0.7245) H13(0.7233) H11(0.7709) H3(0.4686)
 H12(0.7501) H6(1.0314) H5(0.9248) H15a(0.9461) H15b(0.8211) H15c(0.7167)
 H4(0.65)
 Fixed Y: H1AA(0.6155) H9(0.0982) H13(0.5707) H11(0.261) H3(0.2601)
 H12(0.5196) H6(0.7807) H5(0.7451) H15a(0.0579) H15b(-0.1509) H15c(-0.0319)
 H4(0.4885)
 Fixed Z: H1AA(0.245) H9(0.288) H13(0.3684) H11(0.6214) H3(-0.1819)
 H12(0.5628) H6(0.0632) H5(-0.1434) H15a(0.675) H15b(0.635) H15c(0.6556) H4(-
 0.2638)
;
_olex2_submission_special_instructions 'No special instructions were received'