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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/81/4128104.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4128104
loop_
_publ_author_name
'Dale, Harvey J. A.'
'Hodges, George R.'
'Lloyd-Jones, Guy C'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -83.00  13.00   1.00   30.00    --  -13.24 -57.00 150.00   96
  2  ω     -8.00  87.00   1.00   30.00    --   14.65  38.00-150.00   95
  3  ω    -20.00  55.00   1.00   30.00    --   14.65 -99.00  90.00   75
  4  ω    -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       'ω 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/[σ²(Fo²)+(0.0617P)²+0.5503P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.500000 0.63178(8) 0.250000 0.0300(4) Uani 1 2 d S T P
N5 N 0.64959(17) 0.52947(7) 0.37329(17) 0.0273(3) Uani 1 1 d . . .
H5 H 0.638(2) 0.4856(12) 0.374(3) 0.039(5) Uiso 1 1 d . . .
C2 C 0.6669(3) 0.67132(8) 0.3734(3) 0.0414(5) Uani 1 1 d . . .
H2A H 0.649(3) 0.6884(10) 0.487(3) 0.043(5) Uiso 1 1 d . . .
H2B H 0.674(3) 0.7095(12) 0.286(3) 0.051(6) Uiso 1 1 d . . .
C3 C 0.8449(3) 0.62917(9) 0.4448(3) 0.0434(5) Uani 1 1 d . . .
H3A H 0.882(3) 0.6196(10) 0.336(3) 0.045(5) Uiso 1 1 d . . .
H3B H 0.948(3) 0.6544(12) 0.545(3) 0.057(6) Uiso 1 1 d . . .
C4 C 0.8089(2) 0.56320(8) 0.5253(2) 0.0319(4) Uani 1 1 d . . .
H4A H 0.924(2) 0.5325(9) 0.566(2) 0.031(4) Uiso 1 1 d . . .
H4B H 0.779(2) 0.5722(9) 0.637(2) 0.030(4) Uiso 1 1 d . . .
C6 C 0.500000 0.56405(10) 0.250000 0.0239(4) Uani 1 2 d S T P
N7 N 0.58627(17) 0.38731(6) 0.32954(17) 0.0255(3) Uani 1 1 d . . .
N9 N 0.500000 0.27896(9) 0.250000 0.0321(4) Uani 1 2 d S T P
C8 C 0.6301(2) 0.32240(7) 0.3700(2) 0.0271(3) Uani 1 1 d . . .
H8 H 0.746(3) 0.3099(10) 0.479(3) 0.035(4) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 1 0 0.0155
1 1 5 0.2321
-1 -1 -5 0.2321
5 -1 0 0.0155
0 1 0 0.0581
0 -1 0 0.0581
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C2 115.72(19) 2_655 .
C6 N1 C2 122.14(9) . 2_655
C6 N1 C2 122.14(9) . .
C4 N5 H5 120.5(11) . .
C6 N5 H5 116.9(12) . .
C6 N5 C4 121.64(14) . .
N1 C2 H2A 109.1(11) . .
N1 C2 H2B 104.7(12) . .
N1 C2 C3 111.68(13) . .
H2A C2 H2B 112.0(17) . .
C3 C2 H2A 108.6(11) . .
C3 C2 H2B 110.8(12) . .
C2 C3 H3A 110.3(11) . .
C2 C3 H3B 109.3(14) . .
C2 C3 C4 108.98(13) . .
H3A C3 H3B 107.8(17) . .
C4 C3 H3A 109.5(12) . .
C4 C3 H3B 111.0(14) . .
N5 C4 C3 108.44(14) . .
N5 C4 H4A 108.7(10) . .
N5 C4 H4B 109.6(10) . .
C3 C4 H4A 110.6(10) . .
C3 C4 H4B 109.8(10) . .
H4A C4 H4B 109.7(14) . .
N5 C6 N1 120.76(9) 2_655 .
N5 C6 N1 120.76(9) . .
N5 C6 N5 118.49(17) 2_655 .
C8 N7 N7 105.29(9) . 2_655
C8 N9 C8 100.95(17) 2_655 .
N7 C8 N9 114.24(13) . .
N7 C8 H8 120.1(11) . .
N9 C8 H8 125.6(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.466(2) .
N1 C2 1.466(2) 2_655
N1 C6 1.336(2) .
N5 H5 0.87(2) .
N5 C4 1.4514(18) .
N5 C6 1.3338(16) .
C2 H2A 0.99(2) .
C2 H2B 1.02(2) .
C2 C3 1.506(3) .
C3 H3A 1.00(2) .
C3 H3B 0.98(2) .
C3 C4 1.510(2) .
C4 H4A 1.017(17) .
C4 H4B 0.981(18) .
N7 N7 1.377(2) 2_655
N7 C8 1.3272(18) .
N9 C8 1.3461(19) 2_655
N9 C8 1.3461(19) .
C8 H8 0.97(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N5 H5 N7 0.87(2) 1.98(2) 2.8420(17) 170.8(16) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C2 C3 C4 -48.26(18) . .
C2 N1 C2 C3 -162.09(16) 2_655 .
C2 N1 C6 N5 4.54(10) . .
C2 N1 C6 N5 -175.47(10) 2_655 .
C2 N1 C6 N5 4.53(10) 2_655 2_655
C2 N1 C6 N5 -175.46(10) . 2_655
C2 C3 C4 N5 57.26(17) . .
C4 N5 C6 N1 6.66(14) . .
C4 N5 C6 N5 -173.34(14) . 2_655
C6 N1 C2 C3 17.91(16) . .
C6 N5 C4 C3 -38.19(16) . .
N7 N7 C8 N9 0.02(17) 2_655 .
C8 N9 C8 N7 -0.01(7) 2_655 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168333727
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0000 1.0004 0.0000 0.4002 -0.1453 0.2695
1.0001 1.0000 5.0000 -0.0416 -0.0763 -0.5606
-1.0001 -1.0000 -5.0000 0.0416 0.0763 0.5606
5.0000 -1.0004 -0.0000 -0.4002 0.1453 -0.2695
0.0000 1.0001 0.0000 0.0192 0.0294 -0.0078
-0.0000 -1.0001 -0.0000 -0.0192 -0.0294 0.0078
