Regioselective synthesis of indazolo[2,3-a]quinazolines enabled by I2/S-facilitated annulation relay dehydrogenative aromatization of cyclohexanones
Gao, Qinghe; Guo, Yimei; Cao, Penghui; Fan, Guangping; Xu, Yongtao; Chemical Communications  (2023) –; doi:10.1039/D3CC04698B

data_7132268
_publ_section_title
;
 Regioselective synthesis of indazolo[2,3-a]quinazolines enabled by
 I2/S-facilitated annulation relay dehydrogenative aromatization of
 cyclohexanones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04698B
_journal_year                    2023
_chemical_formula_sum            'C21 H12 F3 N3'
_chemical_formula_weight         363.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                97.386(6)
_cell_angle_beta                 107.310(6)
_cell_angle_gamma                93.704(6)
_cell_formula_units_Z            2
_cell_length_a                   9.105(4)
_cell_length_b                   9.483(4)
_cell_length_c                   10.167(4)
_cell_measurement_reflns_used    979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.80
_cell_volume                     826.2(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5161
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    0.112
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2180
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04698b2.cif
_cod_data_source_block           H311_0m
_cod_database_code               7132268
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              10840
_shelx_hkl_checksum              3806