Iodide ion-enabled highly regioselective α-C(sp3)–H triazolization of ethers with N-sulfonyl-1,2,3-triazoles
Deng, Yaqi; Yin, Jiabin; Hu, Zongjing; Xue, Jian; Ji, Jian; Zhu, Tong; Liu, Shunying; New Journal of Chemistry 48 (2024) 15002–15007; doi:10.1039/D4NJ02699C

data_7063397
_publ_section_title
;
 Iodide ion-enabled highly regioselective \a-C(sp3)--H triazolization of
 ethers with N-sulfonyl-1,2,3-triazoles
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15002
_journal_page_last               15007
_journal_paper_doi               10.1039/D4NJ02699C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C12 H12 Br N3 O2'
_chemical_formula_sum            'C12 H12 Br N3 O2'
_chemical_formula_weight         310.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8086(2)
_cell_length_b                   9.1808(2)
_cell_length_c                   9.3863(2)
_cell_measurement_reflns_used    12196
_cell_measurement_temperature    297.52(10)
_cell_measurement_theta_max      74.1340
_cell_measurement_theta_min      3.0060
_cell_volume                     1266.04(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.52(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -52.00  32.00   1.00    1.00    --    0.00 -82.00  60.00   84
  2  \w    -84.00 -57.00   1.00    1.00    --    0.00 -82.00  60.00   27
  3  \w    -44.00  24.00   1.00    1.00    --    0.00 -19.00  90.00   68
  4  \w    -88.00  19.00   1.00    1.00    --    0.00 -37.00 -30.00  107
  5  \w    -19.00  78.00   1.00    1.00    --    0.00  37.00-120.00   97
  6  \w    -85.00 -49.00   1.00    1.00    --    0.00 -19.00  90.00   36
  7  \w      9.00  76.00   1.00    1.00    --    0.00  19.00  30.00   67
  8  \w    -24.00   3.00   1.00    1.00    --    0.00  19.00  30.00   27
  9  \w    -30.00  35.00   1.00    1.00    --    0.00  82.00  90.00   65
 10  \w     41.00  66.00   1.00    1.00    --    0.00  82.00  90.00   25
 11  \w     68.00  94.00   1.00    1.00    --   95.80  74.00  51.97   26
 12  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 13  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 14  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  30.00   26
 15  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00  90.00  122
 16  \w     68.00  94.00   1.00    1.00    --   95.80  68.00 -72.90   26
 17  \w     69.00 105.00   1.00    1.00    --   95.80  65.00-112.90   36
 18  \w    126.00 179.00   1.00    1.00    --   95.80  75.00 -13.97   53
 19  \w     93.00 127.00   1.00    1.00    --   95.80 -82.00-150.00   34
 20  \w     54.00  82.00   1.00    1.00    --   95.80 -82.00-150.00   28
 21  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 22  \w     63.00  94.00   1.00    1.00    --   95.80  82.00  60.00   31
 23  \w     63.00  97.00   1.00    1.00    --   95.80  82.00-180.00   34
 24  \w     65.00  96.00   1.00    1.00    --   95.80  77.00   0.00   31
 25  \w      6.00  71.00   1.00    1.00    --   95.80 -82.00  30.00   65
 26  \w     75.00 104.00   1.00    1.00    --   95.80 -82.00  30.00   29
 27  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 28  \w     63.00  95.00   1.00    1.00    --   95.80  82.00-120.00   32
 29  \w     71.00 109.00   1.00    1.00    --   95.80  61.00  60.00   38
 30  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 31  \w     66.00  91.00   1.00    1.00    --   95.80  75.00 -13.97   25
 32  \w     69.00  95.00   1.00    1.00    --   95.80  67.00 -29.19   26
 33  \w     20.00  48.00   1.00    1.00    --   95.80 -82.00-150.00   28
 34  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   25
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 36  \w     65.00  95.00   1.00    1.00    --   95.80  77.00-150.00   30
 37  \w     75.00 108.00   1.00    1.00    --   95.80  45.00-180.00   33
 38  \w    116.00 142.00   1.00    1.00    --   95.80  45.00-180.00   26
 39  \w     75.00 185.00   1.00    1.00    --   95.80  45.00 -60.00  110
 40  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 41  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 120.00   26
 42  \w    110.00 184.00   1.00    1.00    --   95.80  82.00 120.00   74
 43  \w     37.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   90
 44  \w     76.00 133.00   1.00    1.00    --   95.80  30.00 -90.00   57
 45  \w    136.00 175.00   1.00    1.00    --   95.80  30.00 -90.00   39
 46  \w     75.00 113.00   1.00    1.00    --   95.80  45.00-150.00   38
 47  \w     77.00 180.00   1.00    1.00    --   95.80  45.00  60.00  103
 48  \w     75.00 166.00   1.00    1.00    --   95.80  45.00 120.00   91
 49  \w     68.00  94.00   1.00    1.00    --   95.80  74.00  85.91   26
 50  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 51  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 52  \w    141.00 169.00   1.00    1.00    --   95.80  45.00 150.00   28
 53  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 54  \w     75.00 108.00   1.00    1.00    --   95.80  45.00 150.00   33
 55  \w     95.00 120.00   1.00    1.00    --   95.80 -61.00  30.00   25
 56  \w     72.00  98.00   1.00    1.00    --   95.80  61.00 120.00   26
 57  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 58  \w     65.00  91.00   1.00    1.00    --   95.80  82.00  30.00   26
 59  \w    117.00 185.00   1.00    1.00    --   95.80  82.00  30.00   68
 60  \w     10.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00  118
 61  \w     51.00  76.00   1.00    1.00    --   95.80 -61.00  30.00   25
 62  \w      9.00  44.00   1.00    1.00    --   95.80 -61.00  30.00   35
 63  \w     75.00 173.00   1.00    1.00    --   95.80  45.00 -30.00   98
 64  \w    143.00 176.00   1.00    1.00    --   95.80  74.00  51.97   33
 65  \w    142.00 167.00   1.00    1.00    --   95.80  65.00-112.90   25
 66  \w    114.00 146.00   1.00    1.00    --   95.80  38.00-118.64   32
 67  \w     79.00 104.00   1.00    1.00    --   95.80  38.00-118.64   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0630499000
_diffrn_orient_matrix_UB_12      0.0139327000
_diffrn_orient_matrix_UB_13      0.1428102000
_diffrn_orient_matrix_UB_21      0.0836219000
_diffrn_orient_matrix_UB_22      -0.0187361000
_diffrn_orient_matrix_UB_23      -0.0806084000
_diffrn_orient_matrix_UB_31      0.0041353000
_diffrn_orient_matrix_UB_32      0.1663470000
_diffrn_orient_matrix_UB_33      -0.0211199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26271
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0511P)^2^+0.7540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02699c2.cif
_cod_data_source_block           exp_2860
_cod_depositor_comments          'Adding full bibliography for 7063397.cif.'
_cod_database_code               7063397
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.443
_shelx_estimated_absorpt_t_min   0.284
_reflns_odcompleteness_completeness 100.00
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C5(H5), C4(H4), C8(H8)
;
_shelx_res_checksum              76183
_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 2.633
_oxdiff_exptl_absorpt_empirical_full_min 0.539