Copper(II)-mediated metalloradical activation: denitrogenative/decarboxylative annulation to 3-arylimidazo[1,2-<i>a</i>]pyridines using tetrazolo[1,5-<i>a</i>]pyridines and cinnamic acids.
Ishu, Km; Singh, Krishna Nand; Chemical communications (Cambridge, England) 61 (2025) 10847–10850; doi:10.1039/d5cc01153a

data_7134702
_publ_section_title
;
 Copper(II)-mediated metalloradical activation:
 denitrogenative/decarboxylative annulation to
 3-arylimidazo[1,2-<i>a</i>]pyridines using
 tetrazolo[1,5-<i>a</i>]pyridines and cinnamic acids.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10847
_journal_page_last               10850
_journal_paper_doi               10.1039/d5cc01153a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C13 H9 N3 O2'
_chemical_formula_sum            'C13 H9 N3 O2'
_chemical_formula_weight         239.23
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-01 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                63.202(3)
_cell_angle_beta                 85.744(2)
_cell_angle_gamma                78.104(2)
_cell_formula_units_Z            4
_cell_length_a                   7.2977(2)
_cell_length_b                   13.0084(4)
_cell_length_c                   13.3204(4)
_cell_measurement_reflns_used    12558
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.7330
_cell_measurement_theta_min      3.6830
_cell_volume                     1104.22(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.90a 64-bit (release 14-04-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -94.00 -18.00   0.50    0.83    --  -40.83 135.00  87.00  152
  2  \w    -93.00 -17.00   0.50    0.83    --  -40.83 134.00 -91.00  152
  3  \w     39.00  96.00   0.50    0.83    --   40.83-134.00-158.00  114
  4  \w     39.00  98.00   0.50    0.83    --   40.83-135.00  22.00  118
  5  \w    -93.00 -17.00   0.50    3.31    --  -82.50 134.00 -91.00  152
  6  \w   -148.00 -67.00   0.50    3.31    --  -82.50-134.00-158.00  162
  7  \w   -150.00 -66.00   0.50    3.31    --  -82.50-135.00  22.00  168
  8  \w     89.00 162.00   0.50    3.31    --   96.04 134.00 -91.00  146
  9  \w     88.00 163.00   0.50    3.31    --   96.04 135.00  87.00  150
 10  \w     39.00 119.00   0.50    3.31    --   96.04-134.00-158.00  160
 11  \w     39.00 120.00   0.50    3.31    --   96.04-135.00  22.00  162
 12  \w    -37.00  27.00   0.50    0.83    --  -40.83  32.00  30.00  128
 13  \w   -109.00 -28.00   0.50    0.83    --  -40.83 -32.00 -60.00  162
 14  \w    -24.00  35.00   0.50    0.83    --  -40.83  11.00-180.00  118
 15  \w    -37.00  27.00   0.50    0.83    --  -40.83  32.00 -60.00  128
 16  \w    -24.00  35.00   0.50    0.83    --  -40.83  11.00 -60.00  118
 17  \w    -24.00  35.00   0.50    0.83    --  -40.83  11.00  90.00  118
 18  \w    -28.00  31.00   0.50    0.83    --  -40.83  21.00-120.00  118
 19  \w     18.00  78.00   0.50    0.83    --   40.83-104.00 120.00  120
 20  \w     21.00 108.00   0.50    0.83    --   40.83  54.00  60.00  174
 21  \w    -27.00  64.00   0.50    0.83    --   40.83 -65.00 120.00  182
 22  \w    -27.00  37.00   0.50    0.83    --   40.83 -32.00-150.00  128
 23  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00-120.00   64
 24  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00 -30.00   64
 25  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00 -90.00   64
 26  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00 -60.00   64
 27  \w    -94.00 -18.00   0.50    3.31    --  -82.50 135.00  87.00  152
 28  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00  90.00   64
 29  \w   -156.00 -58.00   0.50    3.31    --  -82.50 -17.00 120.00  196
 30  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00 150.00   64
 31  \w   -156.00 -58.00   0.50    3.31    --  -82.50 -17.00-150.00  196
 32  \w    -47.00 -15.00   0.50    3.31    --  -82.50  42.00   0.00   64
 33  \w     99.00 160.00   0.50    3.31    --   96.04 117.00-120.00  122
 34  \w     81.00 164.00   0.50    3.31    --   96.04 145.00 120.00  166
 35  \w     99.00 160.00   0.50    3.31    --   96.04 117.00 150.00  122
 36  \w     26.00 127.00   0.50    3.31    --   96.04 -87.00-180.00  202
 37  \w     82.00 164.00   0.50    3.31    --   96.04  33.00-120.00  164
 38  \w     44.00 127.00   0.50    3.31    --   96.04-145.00 -30.00  166
 39  \w     81.00 164.00   0.50    3.31    --   96.04 145.00  60.00  166
 40  \w     99.00 160.00   0.50    3.31    --   96.04 117.00 -90.00  122
 41  \w     99.00 160.00   0.50    3.31    --   96.04 117.00-180.00  122
 42  \w     99.00 160.00   0.50    3.31    --   96.04 117.00-150.00  122
 43  \w     28.00  83.00   0.50    3.31    --   96.04 -68.00-180.00  110
 44  \w     81.00 164.00   0.50    3.31    --   96.04 145.00-150.00  166
 45  \w     79.00 162.00   0.50    3.31    --   96.04  42.00   0.00  166
 46  \w     79.00 162.00   0.50    3.31    --   96.04  42.00-180.00  166
 47  \w     44.00 127.00   0.50    3.31    --   96.04-145.00  90.00  166
 48  \w     99.00 160.00   0.50    3.31    --   96.04 117.00 120.00  122
 49  \w     99.00 160.00   0.50    3.31    --   96.04 117.00  60.00  122
 50  \w     29.00  57.00   0.50    3.31    --   96.04 -50.00 -90.00   56
 51  \w     23.00 106.00   0.50    3.31    --   96.04 -96.00  90.00  166
 52  \w     32.00 110.00   0.50    3.31    --   96.04-117.00  90.00  156
 53  \w     79.00 162.00   0.50    3.31    --   96.04  42.00 -90.00  166
 54  \w     29.00  57.00   0.50    3.31    --   96.04 -50.00-180.00   56
 55  \w     28.00  68.00   0.50    3.31    --   96.04 -59.00-150.00   80
 56  \w     28.00  68.00   0.50    3.31    --   96.04 -59.00-120.00   80
 57  \w     28.00  68.00   0.50    3.31    --   96.04 -59.00 -60.00   80
 58  \w     23.00 106.00   0.50    3.31    --   96.04 -96.00 150.00  166
 59  \w   -108.00 -17.00   0.50    0.83    --  -40.83 -65.00 120.00  182
 60  \w   -109.00 -14.00   0.50    0.83    --  -40.83 -77.00  30.00  190
 61  \w    -64.00  27.00   0.50    0.83    --  -40.83  65.00  60.00  182
 62  \w     14.00 110.00   0.50    0.83    --   40.83  77.00 -60.00  192
 63  \w     14.00 110.00   0.50    0.83    --   40.83  77.00  60.00  192
 64  \w     18.00 109.00   0.50    0.83    --   40.83  65.00 -90.00  182
 65  \w     14.00 110.00   0.50    0.83    --   40.83  77.00   0.00  192
 66  \w     14.00 110.00   0.50    0.83    --   40.83  77.00 120.00  192
 67  \w     14.00 110.00   0.50    0.83    --   40.83  77.00 -30.00  192
 68  \w     14.00 110.00   0.50    0.83    --   40.83  77.00-150.00  192
 69  \w     14.00 110.00   0.50    0.83    --   40.83  77.00 -90.00  192
 70  \w     14.00 110.00   0.50    0.83    --   40.83  77.00  30.00  192
 71  \w     14.00 110.00   0.50    0.83    --   40.83  77.00-120.00  192
 72  \w     14.00 110.00   0.50    0.83    --   40.83  77.00  90.00  192
 73  \w     14.00 110.00   0.50    0.83    --   40.83  77.00-180.00  192
 74  \w     18.00 109.00   0.50    0.83    --   40.83  65.00-180.00  182
 75  \w     18.00 109.00   0.50    0.83    --   40.83  65.00 120.00  182
 76  \w     18.00 109.00   0.50    0.83    --   40.83  65.00-120.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0729477000
_diffrn_orient_matrix_UB_12      0.1337114000
_diffrn_orient_matrix_UB_13      -0.0537918000
_diffrn_orient_matrix_UB_21      0.0059945000
_diffrn_orient_matrix_UB_22      -0.0019797000
_diffrn_orient_matrix_UB_23      0.1162326000
_diffrn_orient_matrix_UB_31      0.2029911000
_diffrn_orient_matrix_UB_32      0.0202207000
_diffrn_orient_matrix_UB_33      -0.0198102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21315
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.145
_diffrn_reflns_theta_min         3.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1611P)^2^+0.0110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3231
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01153a2.cif
_cod_data_source_block           is-4no2-xy2
_cod_depositor_comments          'Adding full bibliography for 7134702.cif.'
_cod_database_code               7134702
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.681
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C18(H18), C22(H22), C24(H24), C26(H26), C13(H13), C7(H7),
 C15(H15), C17(H17), C9(H9), C19(H19), C5(H5), C21(H21), C11(H11), C23(H23),
 C3(H3), C25(H25)
;
_shelx_res_checksum              44714
_shelx_hkl_checksum              81076
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.738