Selective Synthesis of Azoloyl <i>NH</i>-1,2,3-Triazoles and Azolyl Diazoketones: Experimental and Computational Insights.
Shafran, Yuri M.; Hussein, Aqeel A.; Beliaev, Nikolai A.; Shevyrin, Vadim A.; Shityakov, Sergey; Beryozkina, Tetyana V.; Bakulev, Vasiliy A.; ACS omega 7 (2022) 5008–5031; doi:10.1021/acsomega.1c05898

data_4519355
_publ_section_title
;
 Selective Synthesis of Azoloyl <i>NH</i>-1,2,3-Triazoles and Azolyl
 Diazoketones: Experimental and Computational Insights.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              5008
_journal_page_last               5031
_journal_paper_doi               10.1021/acsomega.1c05898
_journal_volume                  7
_journal_year                    2022
_chemical_formula_moiety         'C10 H14 N6 O, C H4 O'
_chemical_formula_sum            'C11 H18 N6 O2'
_chemical_formula_weight         266.31
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-06-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.625(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.633(4)
_cell_length_b                   6.8163(8)
_cell_length_c                   25.874(4)
_cell_measurement_reflns_used    1407
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.8980
_cell_measurement_theta_min      3.9870
_cell_volume                     2933.3(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.886
_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    -49.00 -21.70   0.70   60.00    --   22.21 -41.00 -96.00   39
  2  \w    -86.00   0.10   0.70   60.00    --  -23.92 -41.00 -96.00  123
  3  \w     21.00  47.60   0.70   60.00    --  -23.92  41.00  56.00   38
  4  \w    -32.00  -5.40   0.70   60.00    --  -23.92  41.00  56.00   38
  5  \w      2.00  94.40   0.70   60.00    --   22.21  41.00  56.00  132
  6  \w    -68.00 -32.30   0.70   60.00    --  -23.92 178.00 120.00   51
  7  \w    -97.00 -36.80   0.70   60.00    --  -23.92-178.00  30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0276177000
_diffrn_orient_matrix_UB_12      0.0508231000
_diffrn_orient_matrix_UB_13      0.0162036000
_diffrn_orient_matrix_UB_21      -0.0248341000
_diffrn_orient_matrix_UB_22      -0.0184466000
_diffrn_orient_matrix_UB_23      0.0216063000
_diffrn_orient_matrix_UB_31      0.0209568000
_diffrn_orient_matrix_UB_32      -0.0888839000
_diffrn_orient_matrix_UB_33      0.0047493000
_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  0.0520
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            11045
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.434
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.206
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0800P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.2229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1520
_reflns_number_total             3944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05898_si_001.cif
_cod_data_source_block           exp_581
_cod_database_code               4519355
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C1S(H1SA,H1SB,H1SC)
;
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.837