Ruthenium-Catalyzed (Spiro)Annulation of N-Aryl-2,3-dihydrophthalazine-1,4-diones with Quinones to Access Pentacyclic Spiro-Indazolones and Fused-Cinnolines
Naharwal, Sushma; Karishma, Pidiyara; Mahesha, Chikkagundagal K.; Bajaj, Kiran; Mandal, Sanjay; Sakhuja, Rajeev; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00493C

data_7158692
_publ_section_title
;
 Ruthenium-Catalyzed (Spiro)Annulation of
 N-Aryl-2,3-dihydrophthalazine-1,4-diones with Quinones to Access
 Pentacyclic Spiro-Indazolones and Fused-Cinnolines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00493C
_journal_year                    2022
_chemical_formula_moiety         'C21 H14 N2 O4'
_chemical_formula_sum            'C21 H14 N2 O4'
_chemical_formula_weight         358.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-30 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.035(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8392(10)
_cell_length_b                   6.9083(6)
_cell_length_c                   13.2119(11)
_cell_measurement_temperature    298(2)
_cell_volume                     940.71(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24163
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.108
_diffrn_reflns_theta_max         25.108
_diffrn_reflns_theta_min         2.919
_diffrn_source                   'Sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   4(5)
_refine_ls_extinction_coef       0.02(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.706
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.705
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.1454
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3853
_refine_ls_wR_factor_ref         0.4103
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2765
_reflns_number_total             3319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00493c2.cif
_cod_data_source_block           3ba
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158692
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              90835
_shelx_fab_checksum              52502