Iridium-catalyzed [4 + 2] annulation of 1-arylindazolones with α-diazo carbonyl compounds: access to indazolone-fused cinnolines.
Mahesha, Chikkagundagal K.; Agarwal, Devesh S.; Karishma, Pidiyara; Markad, Datta; Mandal, Sanjay K.; Sakhuja, Rajeev; Organic & biomolecular chemistry 16 (2018) 8585–8595; doi:10.1039/c8ob01681j

data_7156530
_publ_section_title
;
 Iridium-catalyzed [4 + 2] annulation of 1-arylindazolones with \a-diazo
 carbonyl compounds: access to indazolone-fused cinnolines.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8585
_journal_page_last               8595
_journal_paper_doi               10.1039/c8ob01681j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H17 Cl N2 O3'
_chemical_formula_sum            'C24 H17 Cl N2 O3'
_chemical_formula_weight         416.84
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_update_record
;
2018-05-04 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                83.094(2)
_cell_angle_beta                 80.207(2)
_cell_angle_gamma                80.262(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5002(7)
_cell_length_b                   9.3931(8)
_cell_length_c                   13.1098(11)
_cell_measurement_reflns_used    3563
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1.583
_cell_volume                     1012.10(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12207
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.58
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.233
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.1488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2899
_reflns_number_total             3563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01681j2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7156530.cif.'
_cod_database_code               7156530
_shelx_res_checksum              96936