Facile preparation of polycyclic halogen-substituted 1,2,3-triazoles by using intramolecular Huisgen cycloaddition.
Kobayashi, Kazuki; Kasakura, Nozomi; Kikukawa, Seiya; Matsumoto, Shota; Karasawa, Satoru; Hata, Takeshi; Organic & biomolecular chemistry 21 (2023) 9610–9615; doi:10.1039/d3ob01283b

data_7159699
_publ_section_title
;
 Facile preparation of polycyclic halogen-substituted 1,2,3-triazoles by
 using intramolecular Huisgen cycloaddition.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9610
_journal_page_last               9615
_journal_paper_doi               10.1039/d3ob01283b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C9 H6 Br N3'
_chemical_formula_sum            'C9 H6 Br N3'
_chemical_formula_weight         236.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.904(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1549(5)
_cell_length_b                   25.864(2)
_cell_length_c                   8.0655(9)
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.2320
_cell_measurement_theta_min      3.3930
_cell_volume                     848.10(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.938
_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    -91.00 -61.00   0.50    5.00    --  -46.45 134.00 148.00   60
  2  \w   -172.00 -98.00   0.50   10.00    -- -102.00  -1.00 135.00  148
  3  \w   -174.00 -81.00   0.50   10.00    -- -102.00-134.00  80.00  186
  4  \w   -168.00 -97.00   0.50   10.00    -- -102.00-132.00 -10.00  142
  5  \w    -16.00  11.00   0.50    5.00    --  -46.45  19.00 -90.00   54
  6  \w    -22.00  27.00   0.50    5.00    --  -46.45  19.00-180.00   98
  7  \w    -27.00  27.00   0.50    5.00    --   46.45 -19.00-180.00  108
  8  \w     38.00  70.00   0.50   10.00    --  104.61 -61.00 -60.00   64
  9  \w     37.00  72.00   0.50   10.00    --  104.61 -61.00  30.00   70
 10  \w     48.00  73.00   0.50   10.00    --  104.61 -61.00 120.00   50
 11  \w    -67.00 -39.00   0.50   10.00    -- -102.00  61.00-180.00   56
 12  \w    -54.00 -28.00   0.50    5.00    --  -46.45 -66.00  36.76   52
 13  \w   -103.00 -72.00   0.50    5.00    --  -46.45 -37.00 -30.00   62
 14  \w    -66.00 -34.00   0.50    5.00    --  -46.45 -37.00  90.00   64
 15  \w   -120.00 -35.00   0.50    5.00    --  -46.45 -37.00-180.00  170
 16  \w   -114.00 -35.00   0.50    5.00    --  -46.45 -37.00-120.00  158
 17  \w    -72.00 -26.00   0.50    5.00    --  -46.45 -72.00 -84.73   92
 18  \w    -93.00 -39.00   0.50    5.00    --  -46.45 125.00  30.00  108
 19  \w    -92.00 -17.00   0.50    5.00    --  -46.45 125.00 -60.00  150
 20  \w   -101.00 -75.00   0.50    5.00    --  -46.45 -67.00 -64.79   52
 21  \w    -52.00 -25.00   0.50    5.00    --  -46.45 -73.00-150.31   54
 22  \w    -67.00 -34.00   0.50    5.00    --  -46.45 -37.00 -30.00   66
 23  \w    -74.00 -36.00   0.50    5.00    --  -46.45 -37.00  30.00   76
 24  \w    -54.00 -28.00   0.50    5.00    --  -46.45 -67.00 -64.79   52
 25  \w    -54.00 -25.00   0.50    5.00    --  -46.45 -73.00  -8.24   58
 26  \w    -53.00 -27.00   0.50    5.00    --  -46.45 -68.00 158.37   52
 27  \w     34.00  61.00   0.50    5.00    --   46.45  57.00  60.00   54
 28  \w     32.00  68.00   0.50    5.00    --   46.45  57.00 150.00   72
 29  \w     32.00  74.00   0.50    5.00    --   46.45  57.00 -90.00   84
 30  \w     25.00  80.00   0.50    5.00    --   46.45  77.00   0.00  110
 31  \w     34.00  77.00   0.50    5.00    --   46.45  57.00-150.00   86
 32  \w     25.00  76.00   0.50    5.00    --   46.45  77.00 150.00  102
 33  \w     85.00 117.00   0.50    5.00    --   46.45  57.00  60.00   64
 34  \w     24.00  76.00   0.50    5.00    --   46.45  77.00 -30.00  104
 35  \w     32.00  70.00   0.50    5.00    --   46.45  57.00 -30.00   76
 36  \w     28.00  72.00   0.50    5.00    --   46.45  68.00  85.67   88
 37  \w   -105.00 -80.00   0.50   10.00    -- -102.00 -74.00  38.82   50
 38  \w   -156.00-130.00   0.50   10.00    -- -102.00 -74.00 -58.91   52
 39  \w   -104.00 -61.00   0.50   10.00    -- -102.00  77.00 120.00   86
 40  \w   -107.00 -80.00   0.50   10.00    -- -102.00 -74.00 -58.91   54
 41  \w   -114.00 -88.00   0.50   10.00    -- -102.00 -48.00 156.76   52
 42  \w   -107.00 -81.00   0.50   10.00    -- -102.00 -72.00 170.67   52
 43  \w   -163.00-137.00   0.50   10.00    -- -102.00 -74.00  38.82   52
 44  \w   -170.00-144.00   0.50   10.00    -- -102.00 -72.00 170.67   52
 45  \w   -108.00 -82.00   0.50   10.00    -- -102.00 -70.00 160.61   52
 46  \w   -136.00 -82.00   0.50   10.00    -- -102.00 -71.00-136.49  108
 47  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00-103.00   52
 48  \w   -168.00-141.00   0.50   10.00    -- -102.00 -79.00-103.00   54
 49  \w   -106.00 -79.00   0.50   10.00    -- -102.00 -76.00  95.18   54
 50  \w   -174.00-127.00   0.50   10.00    -- -102.00 -77.00-120.00   94
 51  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -47.87   52
 52  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00  53.90   52
 53  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00-176.21   52
 54  \w   -107.00 -81.00   0.50   10.00    -- -102.00 -72.00-131.36   52
 55  \w   -105.00 -80.00   0.50   10.00    -- -102.00 -74.00 130.64   50
 56  \w   -106.00 -80.00   0.50   10.00    -- -102.00 -75.00 -19.80   52
 57  \w   -114.00 -78.00   0.50   10.00    -- -102.00 -79.00-148.47   72
 58  \w   -127.00 -79.00   0.50   10.00    -- -102.00 -78.00 105.40   96
 59  \w   -140.00 -80.00   0.50   10.00    -- -102.00 -77.00  -5.64  120
 60  \w   -173.00 -78.00   0.50   10.00    -- -102.00 -79.00 -93.66  190
 61  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -82.72   52
 62  \w   -107.00 -79.00   0.50   10.00    -- -102.00 -77.00 120.00   56
 63  \w   -175.00-147.00   0.50   10.00    -- -102.00 -74.00 130.64   56
 64  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  47.96   52
 65  \w   -108.00 -82.00   0.50   10.00    -- -102.00 -69.00  66.78   52
 66  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 -25.23   52
 67  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00  29.99   52
 68  \w   -175.00 -82.00   0.50   10.00    -- -102.00 -69.00  -1.64  186
 69  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 113.61   52
 70  \w   -175.00-135.00   0.50   10.00    -- -102.00 -74.00 142.75   80
 71  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  90.00   52
 72  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -32.34   52
 73  \w   -103.00 -78.00   0.50   10.00    -- -102.00  77.00-150.00   50
 74  \w   -105.00 -78.00   0.50   10.00    -- -102.00 -80.00   3.08   54
 75  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00 -58.88   52
 76  \w   -174.00 -80.00   0.50   10.00    -- -102.00 -74.00 -16.14  188
 77  \w   -130.00 -80.00   0.50   10.00    -- -102.00 -75.00 -42.04  100
 78  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  35.35   52
 79  \w   -160.00 -82.00   0.50   10.00    -- -102.00 -69.00  71.42  156
 80  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00  16.65   52
 81  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 154.17   52
 82  \w   -173.00-128.00   0.50   10.00    -- -102.00 -76.00 154.17   90
 83  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 137.95   52
 84  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 159.53   52
 85  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  22.08   52
 86  \w   -144.00-118.00   0.50   10.00    -- -102.00 -76.00  16.65   52
 87  \w   -173.00 -80.00   0.50   10.00    -- -102.00 -75.00 113.04  186
 88  \w   -170.00 -79.00   0.50   10.00    -- -102.00 -76.00 -71.68  182
 89  \w   -138.00 -88.00   0.50   10.00    -- -102.00 -53.00-102.91  100
 90  \w   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00-110.93   52
 91  \w   -175.00 -81.00   0.50   10.00    -- -102.00 -72.00  61.09  188
 92  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00 -30.00   52
 93  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  60.00   52
 94  \w   -106.00 -79.00   0.50   10.00    -- -102.00 -77.00-120.00   54
 95  \w   -111.00 -79.00   0.50   10.00    -- -102.00 -77.00-138.93   64
 96  \w   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 125.40   52
 97  \w   -106.00 -80.00   0.50   10.00    -- -102.00 -74.00 142.75   52
 98  \w   -106.00 -80.00   0.50   10.00    -- -102.00 -74.00-162.47   52
 99  \w     41.00  89.00   0.50   10.00    --  104.61 -94.00-120.00   96
100  \w     34.00  86.00   0.50   10.00    --  104.61 -94.00 -30.00  104
101  \w     54.00 104.00   0.50   10.00    --  104.61 -94.00 -90.00  100
102  \w     62.00 105.00   0.50   10.00    --  104.61 -94.00-180.00   86
103  \w     33.00  58.00   0.50   10.00    --  104.61 -94.00-180.00   50
104  \w     32.00  94.00   0.50   10.00    --  104.61 -94.00   0.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0625900000
_diffrn_orient_matrix_UB_12      -0.0247426000
_diffrn_orient_matrix_UB_13      -0.1774847000
_diffrn_orient_matrix_UB_21      -0.0271802000
_diffrn_orient_matrix_UB_22      0.0542449000
_diffrn_orient_matrix_UB_23      -0.0806073000
_diffrn_orient_matrix_UB_31      0.3724234000
_diffrn_orient_matrix_UB_32      -0.0000557000
_diffrn_orient_matrix_UB_33      0.0043847000
_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  0.2096
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.537
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.019
_refine_diff_density_max         3.611
_refine_diff_density_min         -1.513
_refine_diff_density_rms         0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.311
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.1178
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2942
_refine_ls_wR_factor_ref         0.3278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1278
_reflns_number_total             1666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01283b2.cif
_cod_data_source_block           ta1_2_autored
_cod_depositor_comments
'Adding full bibliography for 7159699--7159701.cif.'
_cod_original_cell_volume        848.11(16)
_cod_database_code               7159699
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C9H7Br2N3
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.439
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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(H00A,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C)
;
_shelx_res_checksum              28481
_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 8.566
_oxdiff_exptl_absorpt_empirical_full_min 0.160