Divergent synthesis of pyrrolidone fused pyrimido[1,2-<i>b</i>]indazole through selective trapping of an enone intermediate by 1<i>H</i>-indazol-3-amine.
Shen, Xi; Yu, Zhi-Cheng; Zhou, You; Wu, Yan-Dong; Wu, An-Xin; Chemical communications (Cambridge, England) 60 (2024) 9781–9784; doi:10.1039/d4cc03483j

data_7133480
_publ_section_title
;
 Divergent synthesis of pyrrolidone fused pyrimido[1,2-<i>b</i>]indazole
 through selective trapping of an enone intermediate by
 1<i>H</i>-indazol-3-amine.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9781
_journal_page_last               9784
_journal_paper_doi               10.1039/d4cc03483j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H22 N4 O2'
_chemical_formula_sum            'C31 H22 N4 O2'
_chemical_formula_weight         482.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-30
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.238(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.947(3)
_cell_length_b                   16.244(3)
_cell_length_c                   15.993(3)
_cell_measurement_reflns_used    7865
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.29
_cell_volume                     4771.0(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         1.674
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0817P)^2^+2.0812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3773
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03483j2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7133480--7133481.cif.'
_cod_original_cell_volume        4771.1(13)
_cod_database_code               7133480
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), 
 C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), 
  C30(H30), C31(H31) 
2.b Idealised Me refined as rotating group: 
 C17(H17A,H17B,H17C) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O2(H2A) 
;
_olex2_submission_special_instructions 'No special instructions were received'