Access to pyrido-pyrimidinone and imidazopyridine via Fe(iii)-mediated denitrogenative annulation of tetrazolopyridine with β-keto ester
Sk, Asikul; Banerji, Biswadip; Chemical Communications 61 (2025) 6312–6315; doi:10.1039/D5CC00258C

data_7134345
_publ_section_title
;
 Access to pyrido-pyrimidinone and imidazopyridine via Fe(iii)-mediated
 denitrogenative annulation of tetrazolopyridine with \b-keto ester
;
_journal_issue                   34
_journal_name_full               'Chemical Communications'
_journal_page_first              6312
_journal_page_last               6315
_journal_paper_doi               10.1039/D5CC00258C
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.285
_chemical_name_systematic
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4H-pyrido[1,2-a]pyrimidin-4-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-19
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.390(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7772(7)
_cell_length_b                   12.8183(8)
_cell_length_c                   8.8804(6)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    108.00
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.98
_cell_volume                     1225.72(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      108.00
_diffrn_measured_fraction_theta_full 0.9663
_diffrn_measured_fraction_theta_max 0.9658
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.9663
_diffrn_reflns_Laue_measured_fraction_max 0.9658
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14811
_diffrn_reflns_point_group_measured_fraction_full 0.9663
_diffrn_reflns_point_group_measured_fraction_max 0.9658
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_min         5.36
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1143 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8063.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       needle
_exptl_crystal_F_000             586.119
_exptl_crystal_recrystallization_method 'Slow evaporation of solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2573
_refine_diff_density_min         -0.2273
_refine_diff_density_rms         0.0528
_refine_ls_d_res_high            0.8299
_refine_ls_d_res_low             8.2448
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0468
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0468
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.3357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2090
_reflns_number_total             2175
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc00258c2.cif
_cod_data_source_block           BBAS_84_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7134345--7134346.cif.'
_cod_database_code               7134345
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C11(H11), C1(H1), C2(H2), C3(H3), C4(H4), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'