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_7159701
_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         'C16 H12 N4'
_chemical_formula_sum            'C16 H12 N4'
_chemical_formula_weight         260.30
_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             2022-04-06
_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                78.907(2)
_cell_angle_beta                 79.540(3)
_cell_angle_gamma                76.410(3)
_cell_formula_units_Z            4
_cell_length_a                   9.3536(3)
_cell_length_b                   10.4366(3)
_cell_length_c                   13.3657(4)
_cell_measurement_reflns_used    11432
_cell_measurement_temperature    90
_cell_measurement_theta_max      73.6710
_cell_measurement_theta_min      4.8670
_cell_volume                     1231.75(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.957
_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   -109.00 -61.00   0.50    1.01    --  -41.30 -65.00  93.00   96
  2  \w     20.00  47.00   0.50    1.01    --   41.30  65.00-131.00   54
  3  \w     75.00 100.00   0.50    1.01    --   41.30  65.00-131.00   50
  4  \w   -131.00-100.00   0.50    4.04    -- -104.00 -65.00  93.00   62
  5  \w   -160.00-134.00   0.50    4.04    -- -104.00 -65.00  93.00   52
  6  \w    -63.00 -32.00   0.50    4.04    -- -104.00  65.00-131.00   62
  7  \w    136.00 163.00   0.50    4.04    --  104.88  65.00-131.00   54
  8  \w    102.00 128.00   0.50    4.04    --  104.88  65.00-131.00   52
  9  \w   -113.00 -72.00   0.50    1.01    --  -41.30 -37.00 -90.00   82
 10  \w    -64.00 -21.00   0.50    1.01    --  -41.30 -37.00 -90.00   86
 11  \w   -114.00 -71.00   0.50    1.01    --  -41.30 -57.00-180.00   86
 12  \w    -78.00 -18.00   0.50    1.01    --  -41.30 -37.00  30.00  120
 13  \w    -65.00   7.00   0.50    1.01    --  -41.30  65.00-131.00  144
 14  \w   -119.00 -80.00   0.50    1.01    --  -41.30 -37.00  30.00   78
 15  \w    -55.00 -26.00   0.50    1.01    --  -41.30 -65.00  93.00   58
 16  \w    -67.00 -18.00   0.50    1.01    --  -41.30 -57.00-180.00   98
 17  \w    -95.00 -18.00   0.50    1.01    --  -41.30 125.00   0.00  154
 18  \w    -31.00  29.00   0.50    1.01    --   41.30 -65.00  93.00  120
 19  \w     35.00  61.00   0.50    1.01    --   41.30 -65.00  93.00   52
 20  \w    -37.00 -11.00   0.50    1.01    --  -44.00 -86.00-157.69   52
 21  \w     16.00  41.00   0.50    1.01    --   44.00  81.00 114.05   50
 22  \w     18.00  54.00   0.50    1.01    --   44.00  71.00 -47.14   72
 23  \w     14.00  41.00   0.50    1.01    --   44.00  85.00  -3.50   54
 24  \w     15.00  42.00   0.50    1.01    --   48.00  87.00 128.13   54
 25  \w     13.00  38.00   0.50    1.01    --   48.00  91.00 -53.18   50
 26  \w     13.00  40.00   0.50    1.01    --   48.00  92.00-165.22   54
 27  \w     12.00  37.00   0.50    1.01    --   48.00  92.00  24.04   50
 28  \w     16.00  41.00   0.50    1.01    --   48.00  84.00 173.83   50
 29  \w    106.00 132.00   0.50    1.01    --   60.00  73.00 -21.67   52
 30  \w     33.00  59.00   0.50    1.01    --   60.00  73.00 -21.67   52
 31  \w     34.00  60.00   0.50    1.01    --   60.00  76.00 167.63   52
 32  \w     34.00  60.00   0.50    1.01    --   60.00  75.00-164.30   52
 33  \w     32.00  71.00   0.50    1.01    --   60.00  77.00  26.83   78
 34  \w    107.00 133.00   0.50    1.01    --   60.00  77.00  26.83   52
 35  \w     32.00  60.00   0.50    1.01    --   60.00  76.00 -61.06   56
 36  \w     35.00  60.00   0.50    1.01    --   64.00  77.00-112.52   50
 37  \w    -68.00 -42.00   0.50    1.01    --  -68.00 -73.00  78.36   52
 38  \w     39.00  65.00   0.50    1.01    --   68.00  77.00  54.90   52
 39  \w    -71.00 -45.00   0.50    1.01    --  -72.00 -71.00 116.47   52
 40  \w    -72.00 -46.00   0.50    1.01    --  -72.00 -71.00  97.64   52
 41  \w    -76.00 -50.00   0.50    4.04    --  -76.00 -74.00 -94.31   52
 42  \w    -75.00 -50.00   0.50    4.04    --  -76.00 -69.00 -31.26   50
 43  \w    -73.00 -48.00   0.50    4.04    --  -76.00 -75.00 -59.48   50
 44  \w   -146.00-120.00   0.50    4.04    --  -76.00 -75.00 -59.48   52
 45  \w    -79.00 -53.00   0.50    4.04    --  -80.00 -74.00-131.69   52
 46  \w    -79.00 -53.00   0.50    4.04    --  -80.00 -74.00 173.41   52
 47  \w    -81.00 -56.00   0.50    4.04    --  -80.00 -67.00  37.23   50
 48  \w    -81.00 -55.00   0.50    4.04    --  -80.00 -69.00  87.84   52
 49  \w    -78.00 -53.00   0.50    4.04    --  -80.00 -72.00   7.13   50
 50  \w   -141.00-115.00   0.50    4.04    --  -80.00 -72.00   7.13   52
 51  \w    -85.00 -56.00   0.50    4.04    --  -80.00 -67.00 132.23   58
 52  \w    -83.00 -53.00   0.50    4.04    --  -80.00 -73.00  60.33   60
 53  \w    -83.00 -57.00   0.50    4.04    --  -84.00 -74.00-144.26   52
 54  \w   -158.00-121.00   0.50    4.04    --  -84.00 -72.00 125.27   74
 55  \w    -83.00 -57.00   0.50    4.04    --  -84.00 -72.00 125.27   52
 56  \w    -82.00 -55.00   0.50    4.04    --  -84.00 -76.00-158.83   54
 57  \w    -82.00 -57.00   0.50    4.04    --  -84.00 -72.00-119.15   50
 58  \w    -89.00 -61.00   0.50    4.04    --  -88.00 -73.00  86.54   56
 59  \w     62.00  88.00   0.50    4.04    --   88.00  74.00 129.62   52
 60  \w    -89.00 -63.00   0.50    4.04    --  -92.00 -76.00  -1.76   52
 61  \w    -94.00 -68.00   0.50    4.04    --  -92.00 -65.00 -76.16   52
 62  \w    -91.00 -65.00   0.50    4.04    --  -92.00 -72.00 136.33   52
 63  \w    -94.00 -67.00   0.50    4.04    --  -92.00 -67.00   3.22   54
 64  \w   -149.00-123.00   0.50    4.04    --  -92.00 -67.00   3.22   52
 65  \w   -124.00 -68.00   0.50    4.04    --  -92.00 -65.00  32.73  112
 66  \w   -161.00-134.00   0.50    4.04    --  -92.00 -65.00  32.73   54
 67  \w    -95.00 -69.00   0.50    4.04    --  -92.00 -62.00 -42.88   52
 68  \w   -166.00 -67.00   0.50    4.04    --  -92.00 -68.00 168.09  198
 69  \w   -168.00 -68.00   0.50    4.04    --  -96.00 -74.00  29.57  200
 70  \w   -163.00-120.00   0.50    4.04    --  -96.00 -76.00 -70.23   86
 71  \w   -103.00 -71.00   0.50    4.04    --  -96.00 -66.00 146.78   64
 72  \w   -166.00-139.00   0.50    4.04    --  -96.00 -57.00  55.39   54
 73  \w   -158.00-108.00   0.50    4.04    --  -96.00 -66.00 146.78  100
 74  \w   -151.00 -72.00   0.50    4.04    --  -96.00 -64.00 -97.92  158
 75  \w   -113.00 -67.00   0.50    4.04    --  -96.00 -76.00 -70.23   92
 76  \w   -103.00 -73.00   0.50    4.04    --  -96.00 -57.00  55.39   60
 77  \w    -96.00 -71.00   0.50    4.04    -- -100.00 -77.00 172.83   50
 78  \w   -152.00-126.00   0.50    4.04    -- -100.00 -77.00 172.83   52
 79  \w   -171.00 -72.00   0.50    4.04    -- -100.00 -77.00-134.77  198
 80  \w   -100.00 -73.00   0.50    4.04    -- -100.00 -74.00 135.97   54
 81  \w   -171.00-116.00   0.50    4.04    -- -100.00 -74.00 135.97  110
 82  \w   -131.00 -74.00   0.50    4.04    -- -100.00 -69.00-161.51  114
 83  \w   -138.00 -71.00   0.50    4.04    -- -100.00 -77.00  -0.60  134
 84  \w   -109.00 -30.00   0.50    4.04    -- -104.00 125.00   0.00  158
 85  \w   -100.00 -75.00   0.50    4.04    -- -104.00 -76.00-160.72   50
 86  \w   -155.00-129.00   0.50    4.04    -- -104.00 -76.00-160.72   52
 87  \w    -59.00 -32.00   0.50    4.04    -- -104.00  77.00  30.00   54
 88  \w    -96.00 -62.00   0.50    4.04    -- -104.00  77.00  30.00   68
 89  \w   -170.00 -80.00   0.50    4.04    -- -104.00 -66.00  67.63  180
 90  \w   -171.00 -75.00   0.50    4.04    -- -104.00 -76.00 -20.05  192
 91  \w   -101.00 -76.00   0.50    4.04    -- -104.00 -74.00-102.33   50
 92  \w   -175.00 -76.00   0.50    4.04    -- -104.00 -74.00 -32.49  198
 93  \w   -134.00 -80.00   0.50    4.04    -- -104.00 -72.00-115.83  108
 94  \w   -123.00 -81.00   0.50    4.04    -- -104.00 -67.00 101.97   84
 95  \w   -174.00-128.00   0.50    4.04    -- -104.00 -67.00 101.97   92
 96  \w     35.00  72.00   0.50    4.04    --  104.88 -61.00 120.00   74
 97  \w     50.00  88.00   0.50    4.04    --  104.88 -77.00-120.00   76
 98  \w     59.00 103.00   0.50    4.04    --  104.88 -94.00 120.00   88
 99  \w     72.00  98.00   0.50    4.04    --  104.88 -94.00 -30.00   52
100  \w     32.00  69.00   0.50    4.04    --  104.88 -94.00 -30.00   74
101  \w     69.00 102.00   0.50    4.04    --  104.88 -94.00-120.00   66
102  \w     73.00 111.00   0.50    4.04    --  104.88-125.00-150.00   76
103  \w     41.00 103.00   0.50    4.04    --  104.88 -77.00-180.00  124
104  \w    127.00 173.00   0.50    4.04    --  104.88  77.00 120.00   92
105  \w     78.00 123.00   0.50    4.04    --  104.88  77.00 120.00   90
106  \w     40.00  66.00   0.50    4.04    --  104.88 -94.00-120.00   52
107  \w     31.00 107.00   0.50    4.04    --  104.88-106.00  90.11  152
108  \w     30.00  55.00   0.50    4.04    --  104.88 -45.00 -30.00   50
109  \w     32.00  80.00   0.50    4.04    --  104.88 -65.00  93.00   96
;
_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      -0.0129440000
_diffrn_orient_matrix_UB_12      0.1234849000
_diffrn_orient_matrix_UB_13      -0.0847479000
_diffrn_orient_matrix_UB_21      0.1362591000
_diffrn_orient_matrix_UB_22      0.0354477000
_diffrn_orient_matrix_UB_23      0.0293101000
_diffrn_orient_matrix_UB_31      0.1028424000
_diffrn_orient_matrix_UB_32      -0.0844796000
_diffrn_orient_matrix_UB_33      -0.0777341000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32072
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.363
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     528
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0556P)^2^+0.8636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4163
_reflns_number_total             4815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01283b2.cif
_cod_data_source_block           kk-x_auto
_cod_depositor_comments
'Adding full bibliography for 7159699--7159701.cif.'
_cod_database_code               7159701
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.762
_reflns_odcompleteness_completeness 99.89
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.002 within 2A
C26 \\sim C27 \\sim C9 \\sim C10: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C27(H27A,H27B), C10(H10A,H10B), C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C40(H40), C4(H4), C32(H32), C29(H29), C7(H7), C31(H31), C5(H5),
 C15(H15), C30(H30), C39(H39), C6(H6), C17(H17), C37(H37), C16(H16), C38(H38)
;
_shelx_res_checksum              46495
_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 1.603
_oxdiff_exptl_absorpt_empirical_full_min 0.680