N<sup>2</sup>-site-selective cross-couplings of tetrazoles with indoles.
Zhang, Hui; Tian, Lifang; Li, Qinying; Zheng, Hanwen; Dai, Yuting; Li, Jiawei; Liu, Guanglu; Zhu, Li-Li; Wang, Yahui; Organic & biomolecular chemistry 23 (2025) 7270–7274; doi:10.1039/d5ob00914f

data_7160640
_publ_section_title
;
 N<sup>2</sup>-site-selective cross-couplings of tetrazoles with indoles.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7270
_journal_page_last               7274
_journal_paper_doi               10.1039/d5ob00914f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H17 N5'
_chemical_formula_sum            'C22 H17 N5'
_chemical_formula_weight         351.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2024-11-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-05-18 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                105.551(4)
_cell_angle_beta                 94.197(4)
_cell_angle_gamma                100.884(4)
_cell_formula_units_Z            1
_cell_length_a                   5.5230(2)
_cell_length_b                   9.1066(4)
_cell_length_c                   9.1781(4)
_cell_measurement_reflns_used    7512
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.4380
_cell_measurement_theta_min      4.9670
_cell_volume                     432.96(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.986
_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     50.00  77.00   0.50    0.05    --  104.59 -77.00  30.00   54
  2  \w     44.00  71.00   0.50    0.05    --  104.59 -77.00   0.00   54
  3  \w     75.00 102.00   0.50    0.05    --  104.59 -77.00   0.00   54
  4  \w     32.00  57.00   0.50    0.05    --  104.59 -61.00-180.00   50
  5  \w     35.00  64.00   0.50    0.05    --  104.59 -61.00-150.00   58
  6  \w     38.00  67.00   0.50    0.05    --  104.59 -61.00 -60.00   58
  7  \w    -31.00  -6.00   0.50    0.05    --   44.14 -19.00 -30.00   50
  8  \w     33.00  68.00   0.50    0.05    --  104.59 -61.00 150.00   70
  9  \w     38.00  63.00   0.50    0.05    --  104.59 -61.00 120.00   50
 10  \w     59.00  86.00   0.50    0.05    --   44.14-139.00 -22.00   54
 11  \w     63.00 105.00   0.50    0.05    --  104.59-125.00-120.00   84
 12  \w     77.00 102.00   0.50    0.05    --  104.59-139.00 -22.00   50
 13  \w     41.00 104.00   0.50    0.05    --  104.59 -95.00 -90.00  126
 14  \w     37.00 110.00   0.50    0.05    --  104.59-125.00  30.00  146
 15  \w     30.00  68.00   0.50    0.05    --   44.14-131.00 152.00   76
 16  \w     65.00 111.00   0.50    0.05    --  104.59-131.00 152.00   92
 17  \w     77.00 102.00   0.50    0.05    --  104.59 -95.00 120.00   50
 18  \w     70.00 112.00   0.50    0.05    --   44.14  77.00  60.00   84
 19  \w     70.00 114.00   0.50    0.05    --   44.14 139.00  37.00   88
 20  \w    105.00 132.00   0.50    0.05    --  104.59 131.00-137.00   54
 21  \w     79.00 121.00   0.50    0.05    --  104.59 139.00  37.00   84
 22  \w     23.00  67.00   0.50    0.05    --   44.14  77.00  60.00   88
 23  \w    -27.00  25.00   0.50    0.05    --  -44.14  19.00  60.00  104
 24  \w    -53.00 -24.00   0.50    0.05    --  -97.00  45.00  90.00   58
 25  \w    -90.00 -65.00   0.50    0.05    --  -44.14 139.00  37.00   50
 26  \w   -122.00 -40.00   0.50    0.05    --  -97.00 139.00  37.00  164
 27  \w    -91.00 -28.00   0.50    0.05    --  -44.14 131.00-137.00  126
 28  \w    -89.00 -63.00   0.50    0.05    --  -97.00 131.00-137.00   52
 29  \w    -49.00 -24.00   0.50    0.05    --  -97.00  45.00-180.00   50
 30  \w   -144.00 -79.00   0.50    0.05    --  -97.00 -15.00-120.00  130
 31  \w   -168.00-129.00   0.50    0.05    --  -97.00 -45.00-150.00   78
 32  \w   -116.00 -86.00   0.50    0.05    --  -97.00 -45.00-150.00   60
 33  \w   -116.00 -87.00   0.50    0.05    --  -44.14 -77.00 -60.00   58
 34  \w    -80.00 -46.00   0.50    0.05    --  -44.14 -77.00 -60.00   68
 35  \w   -136.00 -96.00   0.50    0.05    --  -97.00 -15.00   0.00   80
 36  \w   -168.00-138.00   0.50    0.05    --  -97.00 -15.00   0.00   60
 37  \w   -166.00-141.00   0.50    0.05    --  -97.00 -95.00 -90.00   50
 38  \w   -154.00-118.00   0.50    0.05    --  -97.00 -95.00-180.00   72
 39  \w   -131.00-100.00   0.50    0.05    --  -97.00 -95.00 -90.00   62
 40  \w   -146.00-121.00   0.50    0.05    --  -97.00-139.00 -22.00   50
 41  \w   -166.00 -88.00   0.50    0.05    --  -97.00 -95.00   0.00  156
 42  \w   -147.00-122.00   0.50    0.05    --  -97.00-131.00 152.00   50
 43  \w    -55.00 -30.00   0.50    0.05    --  -46.52 139.00  37.00   50
 44  \w    150.00 175.00   0.50    0.05    --  104.59 125.00 120.00   50
 45  \w     80.00 106.00   0.50    0.05    --  104.59 125.00 120.00   52
 46  \w    -86.00 -61.00   0.50    0.05    --  -46.52 131.00-137.00   50
 47  \w     61.00  87.00   0.50    0.05    --  104.59 -95.00-180.00   52
 48  \w     33.00  65.00   0.50    0.05    --   46.52  38.00 -90.00   64
 49  \w    -54.00 -28.00   0.50    0.05    --  -46.52 -63.00-103.20   52
 50  \w     37.00  64.00   0.50    0.05    --   46.52  38.00 120.00   54
 51  \w     25.00  56.00   0.50    0.05    --   46.52  77.00  90.00   62
 52  \w     61.00  87.00   0.50    0.05    --   46.52  77.00 -30.00   52
 53  \w     23.00  49.00   0.50    0.05    --   46.52  77.00-150.00   52
 54  \w     24.00  67.00   0.50    0.05    --   46.52  77.00   0.00   86
 55  \w     35.00  61.00   0.50    0.05    --   46.52  38.00 -60.00   52
 56  \w     74.00 100.00   0.50    0.05    --   46.52  38.00 -60.00   52
 57  \w     30.00  56.00   0.50    0.05    --   46.52  57.00   0.00   52
 58  \w     79.00 105.00   0.50    0.05    --   46.52  57.00   0.00   52
 59  \w     71.00 106.00   0.50    0.05    --   46.52  77.00 150.00   70
 60  \w     32.00  61.00   0.50    0.05    --   46.52  38.00-180.00   58
 61  \w     24.00  64.00   0.50    0.05    --   46.52  77.00 -90.00   80
 62  \w     24.00  50.00   0.50    0.05    --   46.52  77.00 -30.00   52
 63  \w     23.00  62.00   0.50    0.05    --   46.52  77.00 150.00   78
 64  \w     62.00  88.00   0.50    0.05    --   46.52  77.00  90.00   52
 65  \w   -168.00-123.00   0.50    0.05    --  -97.00 -77.00 120.00   90
 66  \w    -98.00 -73.00   0.50    0.05    --  -97.00 -77.00 -30.00   50
 67  \w   -135.00-109.00   0.50    0.05    --  -97.00 -77.00 -30.00   52
 68  \w   -165.00-129.00   0.50    0.05    --  -97.00 -50.00   5.09   72
 69  \w   -100.00 -74.00   0.50    0.05    --  -97.00 -75.00-129.51   52
 70  \w   -123.00 -83.00   0.50    0.05    --  -97.00 -58.00-167.22   80
 71  \w   -111.00 -85.00   0.50    0.05    --  -97.00 -50.00   5.09   52
 72  \w   -114.00 -74.00   0.50    0.05    --  -97.00 -75.00 -69.94   80
 73  \w   -106.00 -73.00   0.50    0.05    --  -97.00 -77.00  60.00   66
 74  \w   -144.00 -76.00   0.50    0.05    --  -97.00 -75.00 165.79  136
 75  \w   -166.00-140.00   0.50    0.05    --  -97.00 -75.00-129.51   52
 76  \w   -158.00-132.00   0.50    0.05    --  -97.00 -75.00-106.52   52
 77  \w   -170.00-120.00   0.50    0.05    --  -97.00 -77.00  90.00  100
 78  \w    -98.00 -73.00   0.50    0.05    --  -97.00 -77.00  90.00   50
 79  \w   -108.00 -82.00   0.50    0.05    --  -97.00 -62.00 119.52   52
 80  \w   -104.00 -73.00   0.50    0.05    --  -97.00 -77.00 150.00   62
 81  \w   -157.00-121.00   0.50    0.05    --  -97.00 -77.00 150.00   72
 82  \w   -106.00 -79.00   0.50    0.05    --  -97.00 -66.00 -94.62   54
 83  \w   -157.00-132.00   0.50    0.05    --  -97.00 -58.00-167.22   50
 84  \w   -101.00 -76.00   0.50    0.05    --  -97.00 -74.00  19.73   50
 85  \w   -106.00 -81.00   0.50    0.05    --  -97.00 -57.00  22.41   50
 86  \w   -112.00 -79.00   0.50    0.05    --  -97.00 -61.00  56.79   66
 87  \w   -104.00 -79.00   0.50    0.05    --  -97.00 -64.00 175.61   50
 88  \w   -149.00-123.00   0.50    0.05    --  -97.00 -57.00  22.41   52
 89  \w   -104.00 -79.00   0.50    0.05    --  -97.00 -61.00-180.00   50
 90  \w   -163.00-138.00   0.50    0.05    --  -97.00 -62.00 119.52   50
 91  \w   -168.00-142.00   0.50    0.05    --  -97.00 -61.00  56.79   52
 92  \w   -104.00 -79.00   0.50    0.05    --  -97.00 -61.00 -30.00   50
 93  \w   -102.00 -74.00   0.50    0.05    --  -97.00 -75.00-106.52   56
 94  \w   -100.00 -75.00   0.50    0.05    --  -97.00 -77.00   0.00   50
 95  \w   -117.00 -73.00   0.50    0.05    --  -97.00 -76.00 -51.85   88
 96  \w   -100.00 -73.00   0.50    0.05    --  -97.00 -77.00 120.00   54
 97  \w   -112.00 -81.00   0.50    0.05    --  -97.00 -61.00  90.00   62
 98  \w   -106.00 -80.00   0.50    0.05    --  -97.00 -64.00  -3.50   52
 99  \w    -98.00 -73.00   0.50    0.05    --  -97.00 -77.00 -90.00   50
100  \w   -165.00-135.00   0.50    0.05    --  -97.00 -64.00 175.61   60
101  \w    -86.00 -61.00   0.50    0.05    --  -46.52 131.00-137.00   50
102  \w   -147.00-122.00   0.50    0.05    --  -97.00-131.00 152.00   50
103  \w     -6.00  19.00   0.50    0.05    --   24.00  91.00 173.91   50
104  \w    -41.00 -15.00   0.50    0.05    --  -44.00 -91.00-149.42   52
105  \w    -84.00 -36.00   0.50    0.05    --  -46.52 -19.00 150.00   96
106  \w     30.00  56.00   0.50    0.05    --   52.00  77.00 -26.97   52
107  \w     29.00  55.00   0.50    0.05    --   52.00  76.00-121.75   52
108  \w     32.00  58.00   0.50    0.05    --   56.00  77.00  60.53   52
109  \w     33.00  59.00   0.50    0.05    --   56.00  77.00 178.55   52
110  \w     37.00  63.00   0.50    0.05    --   56.00  71.00  37.48   52
111  \w     37.00  63.00   0.50    0.05    --   60.00  75.00  76.30   52
112  \w     41.00  67.00   0.50    0.05    --   60.00  71.00-168.66   52
113  \w     37.00  62.00   0.50    0.05    --   60.00  75.00  87.95   50
114  \w    -73.00 -47.00   0.50    0.05    --  -64.00 -64.00 -44.88   52
115  \w     42.00  68.00   0.50    0.05    --   64.00  74.00 104.41   52
116  \w     42.00  68.00   0.50    0.05    --   64.00  73.00 147.42   52
117  \w    -76.00 -50.00   0.50    0.05    --  -68.00 -67.00 -11.41   52
118  \w    -73.00 -47.00   0.50    0.05    --  -68.00 -70.00 106.25   52
119  \w    -78.00 -52.00   0.50    0.05    --  -68.00 -60.00 175.80   52
120  \w     47.00  73.00   0.50    0.05    --   68.00  75.00  78.29   52
121  \w    -83.00 -57.00   0.50    0.05    --  -72.00 -56.00 -77.99   52
122  \w    -80.00 -54.00   0.50    0.05    --  -72.00 -65.00 135.81   52
123  \w    -79.00 -53.00   0.50    0.05    --  -72.00 -68.00 119.13   52
124  \w    -78.00 -53.00   0.50    0.05    --  -72.00 -64.00 -26.06   50
125  \w    -85.00 -59.00   0.50    0.05    --  -76.00 -60.00 168.96   52
126  \w    -87.00 -61.00   0.50    0.05    --  -76.00 -56.00-162.92   52
127  \w    -81.00 -55.00   0.50    0.05    --  -76.00 -71.00  19.47   52
128  \w    -79.00 -54.00   0.50    0.05    --  -76.00 -73.00  35.55   50
129  \w    -86.00 -61.00   0.50    0.05    --  -80.00 -64.00  -4.22   50
130  \w    -83.00 -57.00   0.50    0.05    --  -80.00 -74.00-108.82   52
131  \w    -93.00 -67.00   0.50    0.05    --  -80.00 -59.00 -30.64   52
132  \w    -83.00 -57.00   0.50    0.05    --  -80.00 -75.00 -79.23   52
133  \w    -87.00 -62.00   0.50    0.05    --  -80.00 -61.00 157.96   50
134  \w    -91.00 -65.00   0.50    0.05    --  -84.00 -67.00 -97.00   52
135  \w    -91.00 -65.00   0.50    0.05    --  -84.00 -65.00 135.78   52
136  \w    -92.00 -67.00   0.50    0.05    --  -84.00 -63.00 149.60   50
137  \w    -89.00 -63.00   0.50    0.05    --  -84.00 -74.00 130.57   52
138  \w    -90.00 -64.00   0.50    0.05    --  -84.00 -73.00  30.05   52
139  \w    -88.00 -63.00   0.50    0.05    --  -84.00 -71.00  17.18   50
140  \w    -91.00 -66.00   0.50    0.05    --  -88.00 -73.00-129.75   50
141  \w    -91.00 -66.00   0.50    0.05    --  -88.00 -73.00 -76.36   50
142  \w    -92.00 -67.00   0.50    0.05    --  -88.00 -72.00-111.09   50
143  \w   -101.00 -76.00   0.50    0.05    --  -92.00 -57.00  73.04   50
144  \w    -54.00 -29.00   0.50    0.05    --  -97.00  45.00 -90.00   50
145  \w     88.00 114.00   0.50    0.05    --  104.59  77.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442987000
_diffrn_orient_matrix_UB_12      0.0742399000
_diffrn_orient_matrix_UB_13      0.1741792000
_diffrn_orient_matrix_UB_21      -0.1071862000
_diffrn_orient_matrix_UB_22      -0.1599936000
_diffrn_orient_matrix_UB_23      0.0228320000
_diffrn_orient_matrix_UB_31      0.2619880000
_diffrn_orient_matrix_UB_32      -0.0353326000
_diffrn_orient_matrix_UB_33      0.0050411000
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8895
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         5.045
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.73(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0516P)^2^+0.0632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                2719
_reflns_number_total             2749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00914f2.cif
_cod_data_source_block           95a
_cod_depositor_comments          'Adding full bibliography for 7160640.cif.'
_cod_database_code               7160640
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.891
_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:
 C00D(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_shelx_res_checksum              49991
_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 5.354
_oxdiff_exptl_absorpt_empirical_full_min 0.510