Biocompatible silicomolybdic acid-promoted one-pot expeditious synthesis of 1,2,3-<i>NH</i>-triazoles.
Ansari, Danish; Jaiswal, Manoj K.; Yadav, Mangal S.; Pandey, Vinay K.; Singh, Mayank; Tiwari, Vinod K.; Organic & biomolecular chemistry 23 (2025) 4045–4057; doi:10.1039/d5ob00298b

data_7160445
_publ_section_title
;
 Biocompatible silicomolybdic acid-promoted one-pot expeditious synthesis
 of 1,2,3-<i>NH</i>-triazoles.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4045
_journal_page_last               4057
_journal_paper_doi               10.1039/d5ob00298b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C9 H10 N4'
_chemical_formula_sum            'C9 H10 N4'
_chemical_formula_weight         174.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.055(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.98700(10)
_cell_length_b                   9.0189(2)
_cell_length_c                   19.7788(4)
_cell_measurement_reflns_used    6413
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7520
_cell_measurement_theta_min      4.4540
_cell_volume                     888.33(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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    105.00 170.00   0.50    0.52    --   96.04  96.00 -30.00  130
  2  \w    -35.00  24.00   0.50    0.20    --   40.83 -11.00  90.00  118
  3  \w    -27.00  37.00   0.50    0.20    --   40.83 -32.00  30.00  128
  4  \w    -31.00  28.00   0.50    0.20    --   40.83 -21.00 -60.00  118
  5  \w    -31.00  27.00   0.50    0.20    --   40.83 -20.00 -96.00  116
  6  \w     23.00 106.00   0.50    0.52    --   96.04 -96.00   0.00  166
  7  \w     23.00 106.00   0.50    0.52    --   96.04 -96.00 -90.00  166
  8  \w     44.00 127.00   0.50    0.52    --   96.04-145.00 -60.00  166
  9  \w     41.00 100.00   0.50    0.20    --   40.83-138.00  30.00  118
 10  \w     41.00 100.00   0.50    0.20    --   40.83-138.00 150.00  118
 11  \w     32.00 110.00   0.50    0.52    --   96.04-117.00 120.00  156
 12  \w     27.00 105.00   0.50    0.52    --   96.04 -77.00  90.00  156
 13  \w     27.00 105.00   0.50    0.52    --   96.04 -77.00 120.00  156
 14  \w     28.00  68.00   0.50    0.52    --   96.04 -59.00 150.00   80
 15  \w     28.00  68.00   0.50    0.52    --   96.04 -59.00 120.00   80
 16  \w     28.00  83.00   0.50    0.52    --   96.04 -68.00   0.00  110
 17  \w     29.00  57.00   0.50    0.52    --   96.04 -50.00-120.00   56
 18  \w     28.00  68.00   0.50    0.52    --   96.04 -59.00 -90.00   80
 19  \w     29.00  57.00   0.50    0.52    --   96.04 -50.00-180.00   56
 20  \w     28.00  68.00   0.50    0.52    --   96.04 -59.00 -60.00   80
 21  \w     28.00  68.00   0.50    0.52    --   96.04 -59.00 -30.00   80
 22  \w     29.00  57.00   0.50    0.52    --   96.04 -50.00 150.00   56
 23  \w     71.00 169.00   0.50    0.52    --   96.04  17.00 -90.00  196
 24  \w     69.00 165.00   0.50    0.52    --   96.04  77.00-180.00  192
 25  \w     69.00 165.00   0.50    0.52    --   96.04  77.00-150.00  192
 26  \w     69.00 165.00   0.50    0.52    --   96.04  77.00-120.00  192
 27  \w     72.00 144.00   0.50    0.52    --   96.04  68.00  60.00  144
 28  \w     74.00 163.00   0.50    0.52    --   96.04  59.00  90.00  178
 29  \w     72.00 164.00   0.50    0.52    --   96.04  68.00 120.00  184
 30  \w     69.00 165.00   0.50    0.52    --   96.04  77.00 150.00  192
 31  \w     79.00 162.00   0.50    0.52    --   96.04  42.00 150.00  166
 32  \w     77.00 168.00   0.50    0.52    --   96.04  20.00  70.00  182
 33  \w     79.00 162.00   0.50    0.52    --   96.04  42.00   0.00  166
 34  \w     77.00 163.00   0.50    0.52    --   96.04  50.00 -60.00  172
 35  \w     14.00 110.00   0.50    0.20    --   40.83  77.00   0.00  192
 36  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  60.00  192
 37  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  90.00  192
 38  \w     22.00 113.00   0.50    0.20    --   40.83  20.00  70.00  182
 39  \w     21.00 108.00   0.50    0.20    --   40.83  54.00-180.00  174
 40  \w    -48.00  26.00   0.50    0.20    --  -40.83  43.00 -60.00  148
 41  \w    -68.00 -14.00   0.50    0.52    --  -82.50  59.00-120.00  108
 42  \w    -57.00 -16.00   0.50    0.52    --  -82.50  50.00-180.00   82
 43  \w    -47.00 -15.00   0.50    0.52    --  -82.50  42.00-120.00   64
 44  \w    -57.00 -16.00   0.50    0.52    --  -82.50  50.00 -60.00   82
 45  \w    -27.00  31.00   0.50    0.20    --  -40.83  20.00  70.00  116
 46  \w    -28.00  31.00   0.50    0.20    --  -40.83  21.00 120.00  118
 47  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 150.00  190
 48  \w   -108.00 -17.00   0.50    0.20    --  -40.83 -65.00-150.00  182
 49  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -90.00  190
 50  \w   -113.00 -22.00   0.50    0.20    --  -40.83 -20.00 -96.00  182
 51  \w   -155.00 -64.00   0.50    0.52    --  -82.50 -20.00 -96.00  182
 52  \w   -151.00 -55.00   0.50    0.52    --  -82.50 -77.00  30.00  192
 53  \w   -151.00 -55.00   0.50    0.52    --  -82.50 -77.00 -30.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2300666000
_diffrn_orient_matrix_UB_12      0.0439061000
_diffrn_orient_matrix_UB_13      -0.0512067000
_diffrn_orient_matrix_UB_21      0.1936279000
_diffrn_orient_matrix_UB_22      -0.0098804000
_diffrn_orient_matrix_UB_23      -0.0579690000
_diffrn_orient_matrix_UB_31      -0.0731401000
_diffrn_orient_matrix_UB_32      -0.1646963000
_diffrn_orient_matrix_UB_33      -0.0101509000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11682
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.073
_diffrn_reflns_theta_min         4.477
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0897
_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^)+(0.1023P)^2^+1.3894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.2646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1380
_reflns_number_total             1599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00298b2.cif
_cod_data_source_block           md-100_autored
_cod_depositor_comments          'Adding full bibliography for 7160445.cif.'
_cod_database_code               7160445
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.911
_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. Restrained distances
 H1-N1
 0.98 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C1(H1A), C3(H3)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              70545
_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 8.911
_oxdiff_exptl_absorpt_empirical_full_min 0.624