Regioselective synthesis of 3,4-diarylpyrimido[1,2-<i>b</i>]indazole derivatives enabled by iron-catalyzed ring-opening of styrene oxides.
Cao, Penghui; Fan, Guangping; Zhao, Xiaofei; Ren, Xinyu; Wang, Yuru; Wang, Yuying; Gao, Qinghe; Chemical communications (Cambridge, England) 60 (2024) 11742–11745; doi:10.1039/d4cc03910f

data_7133739
_publ_section_title
;
 Regioselective synthesis of 3,4-diarylpyrimido[1,2-<i>b</i>]indazole
 derivatives enabled by iron-catalyzed ring-opening of styrene oxides.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11742
_journal_page_last               11745
_journal_paper_doi               10.1039/d4cc03910f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 N3'
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.39
_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_date             2023-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2024-07-29 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                80.364(9)
_cell_angle_beta                 67.002(9)
_cell_angle_gamma                73.546(10)
_cell_formula_units_Z            2
_cell_length_a                   9.185(8)
_cell_length_b                   10.136(8)
_cell_length_c                   10.439(9)
_cell_measurement_reflns_used    687
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.84
_cell_volume                     856.2(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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 0.978
_diffrn_measured_fraction_theta_max 0.959
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5080
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_min         2.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.006
_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          0.1555
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1996
_reflns_number_total             3817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03910f2.cif
_cod_data_source_block           C008_0m
_cod_depositor_comments          'Adding full bibliography for 7133739.cif.'
_cod_database_code               7133739
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.079) H7(0.082) H6(0.074) H5(0.064) H4(0.063) H2(0.072)
 H3(0.072) H9(0.075) H8(0.065) H16(0.057) H12(0.066) H10(0.068) H11(0.061)
 H15(0.115) H13(0.115) H14(0.115) H17(0.063)
 Fixed X: H1(0.563748) H7(0.303077) H6(0.174193) H5(0.249966) H4(-0.021573)
 H2(-0.132227) H3(-0.131254) H9(0.695781) H8(0.565967) H16(0.410771)
 H12(0.36547) H10(0.198975) H11(0.143846) H15(0.465786) H13(0.537467)
 H14(0.618108) H17(-0.026092)
 Fixed Y: H1(-0.030459) H7(-0.011474) H6(0.177481) H5(0.282512) H4(0.697284)
 H2(0.926598) H3(1.088511) H9(0.14053) H8(0.332872) H16(0.698339) H12(0.650858)
 H10(0.505251) H11(0.448525) H15(0.87418) H13(0.786532) H14(0.7498)
 H17(1.028324)
 Fixed Z: H1(0.252934) H7(0.412556) H6(0.543511) H5(0.727918) H4(1.001116)
 H2(1.039096) H3(0.854207) H9(0.222465) H8(0.35008) H16(0.318674) H12(-
 0.033845) H10(0.083939) H11(0.318378) H15(0.084948) H13(-0.04578)
 H14(0.067202) H17(0.629124)
;
_shelx_res_checksum              61141
_shelx_hkl_checksum              81087
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'