Catalyst-free microwave-assisted azo-Povarov reaction of <i>N</i>-carbonyl aryldiazenes with <i>trans</i>-cyclooctene to access ring-fused cinnoline derivatives.
Jiménez-Aberásturi, Xabier; Padrones, Gurutze; Vicario, Javier; de Los Santos, Jesús M; Organic & biomolecular chemistry 23 (2025) 6200–6208; doi:10.1039/d5ob00508f

data_7160581
_publ_section_title
;
 Catalyst-free microwave-assisted azo-Povarov reaction of
 <i>N</i>-carbonyl aryldiazenes with <i>trans</i>-cyclooctene to access
 ring-fused cinnoline derivatives.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6200
_journal_page_last               6208
_journal_paper_doi               10.1039/d5ob00508f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C17 H24 N2 O2'
_chemical_formula_sum            'C17 H24 N2 O2'
_chemical_formula_weight         288.38
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jnwkn
_audit_creation_date             2024-03-27T11:47:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                93.0396(13)
_cell_angle_beta                 94.1142(14)
_cell_angle_gamma                101.4945(16)
_cell_formula_units_Z            2
_cell_length_a                   5.78458(12)
_cell_length_b                   7.85285(14)
_cell_length_c                   17.1515(2)
_cell_measurement_reflns_used    10301
_cell_measurement_temperature    181(16)
_cell_measurement_theta_max      73.641
_cell_measurement_theta_min      2.589
_cell_volume                     759.71(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.33a 64-bit (release 26-10-2021))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      181(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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     68.00  94.00   0.50    0.20    --   36.99 -17.00  38.00   52
  2  \w    -46.00 -16.00   0.50    0.20    --   36.99 -17.00  38.00   60
  3  \w     35.00  60.00   0.50    0.20    --   36.99 -17.00  38.00   50
  4  \w     80.00 106.00   0.50    0.80    --  111.20 -17.00  38.00   52
  5  \w     24.00  60.00   0.50    0.80    --  111.20 -17.00  38.00   72
  6  \w    148.00 177.00   0.50    0.80    --  111.20  17.00-152.00   58
  7  \w    -83.00  21.00   0.50    0.20    --  -36.99 -17.00  38.00  208
  8  \w   -118.00 -69.00   0.50    0.20    --  -36.99 -38.00 -90.00   98
  9  \w    -58.00 -33.00   0.50    0.20    --  -36.99  17.00-152.00   50
 10  \w    -63.00  -6.00   0.50    0.20    --  -36.99 -38.00 -90.00  114
 11  \w   -126.00 -42.00   0.50    0.20    --  -36.99-178.00  60.00  168
 12  \w   -125.00 -87.00   0.50    0.20    --  -36.99 -17.00  38.00   76
 13  \w      1.00  86.00   0.50    0.20    --   36.99 -99.00 -60.00  170
 14  \w     15.00  40.00   0.50    0.20    --   36.99  17.00-152.00   50
 15  \w     10.00 112.00   0.50    0.20    --   36.99  57.00-120.00  204
 16  \w     62.00 125.00   0.50    0.20    --   36.99-178.00  90.00  126
 17  \w     -5.00  20.00   0.50    0.20    --   42.00  99.00  -9.25   50
 18  \w      3.00  41.00   0.50    0.20    --   42.00  78.00 113.50   76
 19  \w     -8.00  18.00   0.50    0.20    --   42.00 101.00-145.67   52
 20  \w      8.00  34.00   0.50    0.20    --   54.00  94.00 129.22   52
 21  \w     15.00  40.00   0.50    0.20    --   58.00  91.00  23.06   50
 22  \w     14.00  39.00   0.50    0.20    --   58.00  92.00 -62.30   50
 23  \w     14.00  39.00   0.50    0.20    --   58.00  89.00  79.95   50
 24  \w     15.00  40.00   0.50    0.20    --   58.00  91.00 -38.42   50
 25  \w     14.00  39.00   0.50    0.20    --   58.00  91.00-144.99   50
 26  \w     14.00  40.00   0.50    0.20    --   58.00  91.00 175.70   52
 27  \w     15.00  40.00   0.50    0.20    --   58.00  88.00 -93.68   50
 28  \w     59.00  84.00   0.50    0.20    --   62.00  74.00  44.89   50
 29  \w     26.00  51.00   0.50    0.20    --   62.00  74.00  44.89   50
 30  \w    119.00 149.00   0.50    0.20    --   70.00  77.00-102.86   60
 31  \w     32.00  66.00   0.50    0.20    --   70.00  77.00-102.86   68
 32  \w     32.00  85.00   0.50    0.20    --   70.00  76.00  94.85  106
 33  \w     38.00  64.00   0.50    0.20    --   74.00  75.00 -25.60   52
 34  \w     43.00 129.00   0.50    0.20    --   74.00  63.00 154.32  172
 35  \w     94.00 134.00   0.50    0.80    --   78.00  77.00 105.60   80
 36  \w     40.00  89.00   0.50    0.80    --   78.00  77.00 105.60   98
 37  \w    117.00 144.00   0.50    0.80    --   78.00  76.00-166.46   54
 38  \w     46.00  72.00   0.50    0.80    --   78.00  72.00   9.79   52
 39  \w     40.00  72.00   0.50    0.80    --   78.00  76.00-166.46   64
 40  \w     45.00  79.00   0.50    0.80    --   82.00  77.00-144.85   68
 41  \w     46.00  82.00   0.50    0.80    --   82.00  75.00 -72.90   72
 42  \w     51.00 129.00   0.50    0.80    --   82.00  59.00 173.89  156
 43  \w    122.00 160.00   0.50    0.80    --   86.00  76.00  22.61   76
 44  \w     48.00 110.00   0.50    0.80    --   86.00  76.00  22.61  124
 45  \w    106.00 158.00   0.50    0.80    --   86.00  77.00 -47.40  104
 46  \w     48.00 100.00   0.50    0.80    --   86.00  77.00 -47.40  104
 47  \w     52.00 169.00   0.50    0.80    --   90.00  77.00-132.71  234
 48  \w     55.00  94.00   0.50    0.80    --   90.00  74.00 -22.97   78
 49  \w    117.00 168.00   0.50    0.80    --   90.00  74.00 -22.97  102
 50  \w     53.00  85.00   0.50    0.80    --   90.00  74.00-101.05   64
 51  \w     63.00  89.00   0.50    0.80    --   94.00  70.00  94.88   52
 52  \w     58.00 123.00   0.50    0.80    --   94.00  76.00  48.48  130
 53  \w    113.00 176.00   0.50    0.80    --  102.00  60.00 169.18  126
 54  \w     71.00 105.00   0.50    0.80    --  102.00  60.00 169.18   68
 55  \w     81.00 170.00   0.50    0.80    --  111.20  61.00   0.00  178
 56  \w    139.00 165.00   0.50    0.80    --  111.20  77.00-180.00   52
 57  \w     78.00 152.00   0.50    0.80    --  111.20  77.00 120.00  148
 58  \w     79.00 144.00   0.50    0.80    --  111.20  61.00 120.00  130
 59  \w     79.00 148.00   0.50    0.80    --  111.20  61.00 -60.00  138
 60  \w     35.00  96.00   0.50    0.80    --  111.20 -95.00-150.00  122
 61  \w     76.00 102.00   0.50    0.80    --  111.20 -95.00-120.00   52
 62  \w     43.00  71.00   0.50    0.80    --  111.20 -95.00-120.00   56
 63  \w     73.00 103.00   0.50    0.80    --  111.20  77.00   0.00   60
 64  \w     75.00 111.00   0.50    0.80    --  111.20  77.00-180.00   72
 65  \w     38.00 108.00   0.50    0.80    --  111.20-112.00  90.00  140
 66  \w     78.00 121.00   0.50    0.80    --  111.20  77.00  30.00   86
 67  \w    140.00 178.00   0.50    0.80    --  111.20  61.00 -90.00   76
 68  \w     83.00 109.00   0.50    0.80    --  111.20  61.00 -90.00   52
 69  \w     29.00 103.00   0.50    0.80    --  111.20 -95.00 -30.00  148
 70  \w    147.00 173.00   0.50    0.80    --  111.20  77.00 -60.00   52
 71  \w     77.00 120.00   0.50    0.80    --  111.20  77.00 -60.00   86
 72  \w     32.00  87.00   0.50    0.80    --  111.20 -95.00  30.00  110
 73  \w    122.00 178.00   0.50    0.80    --  111.20 112.00  60.00  112
 74  \w    122.00 169.00   0.50    0.80    --  111.20  77.00-150.00   94
 75  \w     73.00 113.00   0.50    0.80    --  111.20  77.00-150.00   80
 76  \w     73.00 118.00   0.50    0.80    --  111.20  77.00 -90.00   90
 77  \w    105.00 153.00   0.50    0.80    --  111.20 112.00  30.00   96
 78  \w     73.00 169.00   0.50    0.80    --  111.20  77.00 150.00  192
 79  \w     74.00  99.00   0.50    0.80    --  111.20  77.00-120.00   50
 80  \w     39.00 100.00   0.50    0.80    --  111.20 -95.00 120.00  122
 81  \w     68.00 108.00   0.50    0.80    --  111.20-112.00   0.00   80
 82  \w     73.00 149.00   0.50    0.80    --  111.20  77.00  60.00  152
 83  \w     31.00  59.00   0.50    0.80    --  111.20-112.00   0.00   56
 84  \w    153.00 178.00   0.50    0.80    --  111.20 -17.00  38.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2241188
_diffrn_orient_matrix_UB_12      0.0773169
_diffrn_orient_matrix_UB_13      -0.0104296
_diffrn_orient_matrix_UB_21      0.151925
_diffrn_orient_matrix_UB_22      0.1847299
_diffrn_orient_matrix_UB_23      0.0172474
_diffrn_orient_matrix_UB_31      0.0328099
_diffrn_orient_matrix_UB_32      0.0128659
_diffrn_orient_matrix_UB_33      -0.0879885
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14481
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         2.589
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
        Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.386
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.1658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0
_reflns_number_gt                2794
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00508f2.cif
_cod_data_source_block           b20220250_xja219adducu
_cod_depositor_comments          'Adding full bibliography for 7160581.cif.'
_cod_database_code               7160581