[3-(Trifluoromethyl)-1<i>H</i>-1,2,4-triazol-5-yl]methylamine derivatives: synthesis, ways of modification and use for peptides labeling.
Khomenko, Dmytro M.; Vashchenko, Oleksandr V.; Doroshchuk, Roman O.; Ivanova, Hanna V.; Raspertova, Ilona V.; Kozytskyi, Andrii V.; Hanson, George S. M.; Coxon, Christopher R.; Shova, Sergiu; Lampeka, Rostyslav D.; Organic & biomolecular chemistry 23 (2025) 8230–8245; doi:10.1039/d5ob01080b

data_7160687
_publ_section_title
;
 [3-(Trifluoromethyl)-1<i>H</i>-1,2,4-triazol-5-yl]methylamine
 derivatives: synthesis, ways of modification and use for peptides
 labeling.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8230
_journal_page_last               8245
_journal_paper_doi               10.1039/d5ob01080b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '3(C4 H5 F3 N4), H2 O'
_chemical_formula_sum            'C12 H17 F9 N12 O'
_chemical_formula_weight         516.38
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-22 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                65.612(5)
_cell_angle_beta                 80.451(4)
_cell_angle_gamma                89.034(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6652(5)
_cell_length_b                   11.6950(6)
_cell_length_c                   11.7268(6)
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    180.05(10)
_cell_measurement_theta_max      25.9630
_cell_measurement_theta_min      1.9190
_cell_volume                     1065.59(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.855
_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    -84.00 -59.00   1.00   30.00    --  -15.29 172.00 -40.00   25
  2  \w    -51.00 -26.00   1.00   30.00    --  -15.29 115.00 177.00   25
  3  \w      3.00  28.00   1.00   30.00    --   17.63-115.00  88.00   25
  4  \w     45.00  71.00   1.00   30.00    --   17.63-172.00 -53.00   26
  5  \w    -31.00   3.00   1.00   30.00    --  -15.29 -77.00 -60.00   34
  6  \w    -34.00  54.00   1.00   30.00    --  -15.29  38.00 -30.00   88
  7  \w    -80.00 -12.00   1.00   30.00    --  -15.29 -57.00-150.00   68
  8  \w      1.00  80.00   1.00   30.00    --   17.63  38.00  60.00   79
  9  \w     39.00  72.00   1.00   30.00    --   17.63 178.00-120.00   33
 10  \w    -20.00  54.00   1.00   30.00    --   17.63 -99.00  90.00   74
 11  \w     -9.00  30.00   1.00   30.00    --   17.63  77.00-180.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0378295000
_diffrn_orient_matrix_UB_12      0.0447518000
_diffrn_orient_matrix_UB_13      0.0196375000
_diffrn_orient_matrix_UB_21      -0.0259070000
_diffrn_orient_matrix_UB_22      -0.0482248000
_diffrn_orient_matrix_UB_23      0.0614863000
_diffrn_orient_matrix_UB_31      0.0693585000
_diffrn_orient_matrix_UB_32      0.0109932000
_diffrn_orient_matrix_UB_33      0.0195665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.359
_diffrn_reflns_theta_min         1.915
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
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    1.609
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0467P)^2^+0.9538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1368
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3453
_reflns_number_total             5011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01080b2.cif
_cod_data_source_block           shs_6457_rola_auto
_cod_depositor_comments
'Adding full bibliography for 7160687--7160688.cif.'
_cod_original_cell_volume        1065.58(10)
_cod_database_code               7160687
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H4N4F3O2
_chemical_oxdiff_usercomment     AV_F2
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4A(H4AD,H4AE), C4B(H4BD,H4BE), C4C(H4CD,H4CE)
;
_shelx_res_checksum              49563
_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 1.020
_oxdiff_exptl_absorpt_empirical_full_min 0.980