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_7134346
_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         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.248
_chemical_name_systematic
2-(benzo[d][1,3]dioxol-5-yl)imidazo[1,2-a]pyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_Int_Tables_number      13
_audit_creation_date             2024-02-19
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.337(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4261(6)
_cell_length_b                   6.7139(2)
_cell_length_c                   19.0884(7)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    121.00
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.10
_cell_volume                     2173.06(13)
_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)'
_diffrn_ambient_temperature      121.00
_diffrn_measured_fraction_theta_full 0.9621
_diffrn_measured_fraction_theta_max 0.9566
_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  0.0617
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.9621
_diffrn_reflns_Laue_measured_fraction_max 0.9566
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            103152
_diffrn_reflns_point_group_measured_fraction_full 0.9621
_diffrn_reflns_point_group_measured_fraction_max 0.9566
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         2.61
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5330
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1578 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.7077.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             995.511
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3109
_refine_diff_density_min         -0.3050
_refine_diff_density_rms         0.0724
_refine_ls_d_res_high            0.8301
_refine_ls_d_res_low             16.9561
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0416
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0416
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0958P)^2^+0.9876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3732
_reflns_number_total             3810
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc00258c2.cif
_cod_data_source_block           BBAS_144_a
_cod_depositor_comments
'Adding full bibliography for 7134345--7134346.cif.'
_cod_database_code               7134346
_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:
 C14(H14a,H14b), C010(H01a,H01b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C13(H13), C00V(H00V), C00N(H00N), C00B(H00B), C1(H1),
 C2(H2), C3(H3), C4(H4), C00T(H00T), C00Y(H00Y), C00P(H00P), C00G(H00G),
 C00C(H00C), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'