ANRORC-type reactions of azolo[1,5-a]pyrimidine-6-carbonitriles with O- and N-nucleophiles
Aminov, Semen V.; Fedotov, Victor V.; Savateev, Konstantin V.; Neymash, Artyom O.; Ulomsky, Evgeny N.; Slepukhin, Pavel A.; Rusinov, Vladimir L.; New Journal of Chemistry 49 (2025) 8627–8631; doi:10.1039/D5NJ00255A

data_7063804
_publ_section_title
;
 ANRORC-type reactions of azolo[1,5-a]pyrimidine-6-carbonitriles with O-
 and N-nucleophiles
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8627
_journal_page_last               8631
_journal_paper_doi               10.1039/D5NJ00255A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 N6 O S'
_chemical_formula_sum            'C18 H16 N6 O S'
_chemical_formula_weight         364.43
_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             2024-10-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                91.963(3)
_cell_angle_beta                 96.868(3)
_cell_angle_gamma                93.117(4)
_cell_formula_units_Z            4
_cell_length_a                   6.7798(3)
_cell_length_b                   10.5381(5)
_cell_length_c                   24.4272(10)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.9130
_cell_measurement_theta_min      2.5230
_cell_volume                     1728.68(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.852
_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     -4.00  31.00   1.00   15.00    --   23.14  77.00  60.00   35
  2  \w    -40.00  38.00   1.00   15.00    --   23.14 -57.00  60.00   78
  3  \w     -1.00  28.00   1.00   15.00    --   23.14  77.00-180.00   29
  4  \w     -4.00  30.00   1.00   15.00    --   23.14  77.00 -60.00   34
  5  \w    -39.00  36.00   1.00   15.00    --   23.14 -57.00 -60.00   75
  6  \w    -39.00  38.00   1.00   15.00    --   23.14 -57.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.759
_diffrn_reflns_theta_min         2.512
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         9203
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0553
_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^)+(0.1000P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6020
_reflns_number_total             9203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00255a2.cif
_cod_data_source_block           exp_1349
_cod_depositor_comments
'Adding full bibliography for 7063804--7063806.cif.'
_cod_database_code               7063804
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Restrained distances
 C18-C19
 1.4 with sigma of 0.02
 C4-C20
 1.4 with sigma of 0.02
 C17-C4
 1.4 with sigma of 0.02
 S3-C19
 1.65 with sigma of 0.02
 S3-C17
 1.65 with sigma of 0.02
 C18-C17
 1.4 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C18)
3. Others
 Fixed Sof: S1(0.8) C18(0.8) H18(0.8) H19(0.8) H19A(0.2) H20(0.8) H20A(0.2)
 S3(0.2) C4(0.2) H4(0.2)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C19(H19A),
  C20(H20), C20(H20A), C7A(H7A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
  C18A(H18A), C19A(H19B), C20A(H20B), C4(H4)
4.b X=CH2 refined with riding coordinates:
 N5A(H5AA,H5AB)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC)
;
_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
;