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_4519354
_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 H6 N6 O3'
_chemical_formula_sum            'C10 H6 N6 O3'
_chemical_formula_weight         258.21
_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     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                91.354(10)
_cell_angle_beta                 92.008(9)
_cell_angle_gamma                92.293(12)
_cell_formula_units_Z            2
_cell_length_a                   5.6104(7)
_cell_length_b                   5.7380(10)
_cell_length_c                   17.8464(17)
_cell_measurement_reflns_used    753
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.3910
_cell_measurement_theta_min      3.8340
_cell_volume                     573.53(13)
_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 0.986
_diffrn_measured_fraction_theta_max 0.980
_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    -46.00 -21.00   1.00  100.00    --   21.89 -64.00 -60.00   25
  2  \w     55.00  89.00   1.00  100.00    --   21.89  64.00  76.00   34
  3  \w    -46.00   5.00   1.00  100.00    --  -23.61  64.00  76.00   51
  4  \w     18.00  44.00   1.00  100.00    --  -23.61  64.00  76.00   26
  5  \w     32.00  98.00   1.00  100.00    --   21.89-178.00 -30.00   66
  6  \w    -93.00   5.00   1.00  100.00    --  -23.61 -77.00-180.00   98
  7  \w   -100.00 -48.00   1.00  100.00    --  -23.61 178.00  30.00   52
  8  \w    -87.00  -3.00   1.00  100.00    --  -23.61 -64.00 -60.00   84
;
_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      0.0142702000
_diffrn_orient_matrix_UB_12      -0.0845938000
_diffrn_orient_matrix_UB_13      -0.0289498000
_diffrn_orient_matrix_UB_21      0.1192436000
_diffrn_orient_matrix_UB_22      0.0423224000
_diffrn_orient_matrix_UB_23      -0.0040846000
_diffrn_orient_matrix_UB_31      0.0400923000
_diffrn_orient_matrix_UB_32      -0.0797947000
_diffrn_orient_matrix_UB_33      0.0269777000
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5290
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.428
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41602
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0400P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1214
_reflns_number_total             2804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05898_si_002.cif
_cod_data_source_block           exp_580
_cod_database_code               4519354
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C3(H3)
;
_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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.610