Unorthodox cascade reaction of arynes and N-nitrosamides leading to indazole scaffolds
Sureshbabu, Popuri; Bhajammanavar, Vinod; Subramanian, Venkatesan; Choutipalli, Venkata Surya Kumar; Baidya, Mahiuddin; Chemical Communications  (2022) –; doi:10.1039/D1CC05655G

data_7129430
_publ_section_title
;
 Unorthodox cascade reaction of arynes and N-nitrosamides leading to
 indazole scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05655G
_journal_year                    2022
_chemical_formula_moiety         'C14 H9 I N2 O'
_chemical_formula_sum            'C14 H9 I N2 O'
_chemical_formula_weight         348.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-09-21 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.256(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3661(4)
_cell_length_b                   23.242(2)
_cell_length_c                   12.7698(12)
_cell_measurement_reflns_used    9073
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      3.20
_cell_volume                     1290.4(2)
_computing_cell_refinement       'Bruker Apex3'
_computing_data_collection       'Bruker Apex3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'ORTEP, L.J.Farrugia, (2012)J. Appl. Cryst. 45, 849-854'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 venture PHOTON II diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20496
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_min         3.506
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  0.5964
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0206P)^2^+0.3812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0459
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3684
_reflns_number_total             3837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05655g2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7129430
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.524
_shelx_estimated_absorpt_t_max   0.708
_shelx_res_checksum              7715
_shelx_hkl_checksum              96391