Taming Ambident Triazole Anions: Regioselective Ion Pairing Catalyzes Direct N-Alkylation with Atypical Regioselectivity.
Dale, Harvey J. A.; Hodges, George R.; Lloyd-Jones, Guy C; Journal of the American Chemical Society 141 (2019) 7181–7193; doi:10.1021/jacs.9b02786

data_4128104
_publ_section_title
;
 Taming Ambident Triazole Anions: Regioselective Ion Pairing Catalyzes
 Direct N-Alkylation with Atypical Regioselectivity.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7181
_journal_page_last               7193
_journal_paper_doi               10.1021/jacs.9b02786
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C7 H14 N3, C2 H2 N3'
_chemical_formula_sum            'C9 H16 N6'
_chemical_formula_weight         208.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.514(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7496(8)
_cell_length_b                   19.7233(15)
_cell_length_c                   7.5396(8)
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.5180
_cell_measurement_theta_min      3.6090
_cell_volume                     1048.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.904
_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    -83.00  13.00   1.00   30.00    --  -13.24 -57.00 150.00   96
  2  \w     -8.00  87.00   1.00   30.00    --   14.65  38.00-150.00   95
  3  \w    -20.00  55.00   1.00   30.00    --   14.65 -99.00  90.00   75
  4  \w    -57.00  37.00   1.00   30.00    --   14.65 -77.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0762146000
_diffrn_orient_matrix_UB_12      0.0191645000
_diffrn_orient_matrix_UB_13      0.0030847000
_diffrn_orient_matrix_UB_21      0.0349395000
_diffrn_orient_matrix_UB_22      0.0294193000
_diffrn_orient_matrix_UB_23      -0.0281278000
_diffrn_orient_matrix_UB_31      -0.0554602000
_diffrn_orient_matrix_UB_32      -0.0077577000
_diffrn_orient_matrix_UB_33      -0.0994755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5465
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.222
_diffrn_reflns_theta_min         3.068
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.071
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method
'The material was recrystallised from dichloromethane by slow evaporation'
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0617P)^2^+0.5503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1264
_reflns_number_total             1553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02786_si_004.cif
_cod_data_source_block           gl18002
_cod_database_code               4128104
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H16 N6'
_chemical_oxdiff_usercomment     '@ 120 K TBDHTRZ'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
;
_shelx_res_checksum              36300
_shelx_hkl_checksum              53444
_olex2_date_sample_data_collection 2018-06-05
_olex2_date_sample_submission    2018-06-05
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id TBDHTRZ
_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 2.029
_oxdiff_exptl_absorpt_empirical_full_min 0.374