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_7159700
_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         'C13 H11 N3 O'
_chemical_formula_sum            'C13 H11 N3 O'
_chemical_formula_weight         225.25
_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             2022-01-13
_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                 118.495(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0182(5)
_cell_length_b                   13.7411(4)
_cell_length_c                   9.4416(5)
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    90
_cell_measurement_theta_max      74.9020
_cell_measurement_theta_min      6.2220
_cell_volume                     1028.27(11)
_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 0.960
_diffrn_measured_fraction_theta_max 0.920
_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    124.00 166.00   0.50   30.00    --  105.67 105.00 -48.00   84
  2  \w     85.00 178.00   0.50   30.00    --  105.67  39.00  96.00  186
  3  \w     39.00 104.00   0.50   30.00    --  105.67 -89.00 106.00  130
  4  \w     94.00 121.00   0.50   30.00    --  105.67 105.00 -48.00   54
  5  \w    -28.00  22.00   0.50   40.00    --  -41.39  37.00-150.00  100
  6  \w    -10.00  16.00   0.50   40.00    --  -41.39  19.00 -30.00   52
  7  \w      5.00  31.00   0.50   40.00    --  -41.39  19.00  30.00   52
  8  \w    -23.00  72.00   0.50   40.00    --   41.39 -89.00 106.00  190
  9  \w    -56.00 -31.00   0.50   30.00    -- -102.00  61.00 150.00   50
 10  \w    -60.00 -31.00   0.50   30.00    -- -102.00  61.00  90.00   58
 11  \w    -85.00 -43.00   0.50   30.00    -- -102.00  77.00 -30.00   84
 12  \w   -124.00 -86.00   0.50   30.00    -- -102.00 -94.00-180.00   76
 13  \w     46.00  72.00   0.50   30.00    --  105.67 -61.00 -30.00   52
 14  \w     40.00  77.00   0.50   30.00    --  105.67 -61.00 150.00   74
 15  \w     35.00  62.00   0.50   30.00    --  105.67 -45.00 150.00   54
 16  \w     31.00  62.00   0.50   30.00    --  105.67 -45.00 -60.00   62
 17  \w    131.00 178.00   0.50   30.00    --  105.67  61.00 -90.00   94
 18  \w     82.00 124.00   0.50   30.00    --  105.67  61.00 -90.00   84
;
_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      0.1045350000
_diffrn_orient_matrix_UB_12      0.0171590000
_diffrn_orient_matrix_UB_13      -0.0876376000
_diffrn_orient_matrix_UB_21      -0.0587924000
_diffrn_orient_matrix_UB_22      0.1068652000
_diffrn_orient_matrix_UB_23      -0.0299920000
_diffrn_orient_matrix_UB_31      0.1527913000
_diffrn_orient_matrix_UB_32      0.0292973000
_diffrn_orient_matrix_UB_33      0.1609786000
_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  0.0200
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4567
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.398
_diffrn_reflns_theta_min         5.585
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80308
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0720P)^2^+0.2346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1673
_reflns_number_total             1928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01283b2.cif
_cod_data_source_block           kk-1_auto
_cod_depositor_comments
'Adding full bibliography for 7159699--7159701.cif.'
_cod_original_cell_volume        1028.27(10)
_cod_database_code               7159700
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.902
_reflns_odcompleteness_completeness 95.59
_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:
 C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C15(H15)
;
_shelx_res_checksum              58609
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.822