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_7063806
_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 H23 N7'
_chemical_formula_sum            'C18 H23 N7'
_chemical_formula_weight         337.43
_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                99.885(4)
_cell_angle_beta                 93.772(4)
_cell_angle_gamma                106.915(4)
_cell_formula_units_Z            4
_cell_length_a                   9.5201(5)
_cell_length_b                   12.7114(6)
_cell_length_c                   16.2360(8)
_cell_measurement_reflns_used    3614
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5970
_cell_measurement_theta_min      2.3830
_cell_volume                     1837.86(17)
_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 0.993
_diffrn_measured_fraction_theta_max 0.843
_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  44.00   1.00   20.00    --   23.14 -57.00  90.00   90
  2  \w      7.00  92.00   1.00   20.00    --   23.14  57.00   0.00   85
  3  \w     -7.00  38.00   1.00   20.00    --   23.14  77.00  90.00   45
  4  \w     -7.00  20.00   1.00   20.00    --   23.14  77.00 -30.00   27
  5  \w      2.00  92.00   1.00   20.00    --   23.14  57.00-120.00   90
;
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14416
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.862
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81871
_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    1.220
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         9768
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1412
_refine_ls_R_factor_gt           0.0694
_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          0.1711
_refine_ls_wR_factor_ref         0.2261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4889
_reflns_number_total             9768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00255a2.cif
_cod_data_source_block           exp_1376
_cod_depositor_comments
'Adding full bibliography for 7063804--7063806.cif.'
_cod_original_cell_volume        1837.86(16)
_cod_database_code               7063806
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Restrained distances
 C19B-C18B
 1.54 with sigma of 0.02
 C19A-C20A
 1.54 with sigma of 0.02
 C18A-C19A
 1.54 with sigma of 0.02
 C19B-C20A
 1.54 with sigma of 0.02
 C18A-C17A
 1.54 with sigma of 0.02
 C17A-C18B
 1.54 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C17C) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H18E(0.5) H18F(0.5) H18G(0.5) H18H(0.5) H17A(0.6) H17B(0.6)
 H17C(0.4) H17D(0.4) C17(0.5) H17E(0.5) H17F(0.5) C18A(0.6) H18A(0.6) H18B(0.6)
 C19A(0.6) H19A(0.6) H19B(0.6) H20A(0.6) H20B(0.6) H20C(0.6) H20D(0.4)
 H20E(0.4) H20F(0.4) C18B(0.4) H18C(0.4) H18D(0.4) C19B(0.4) H19C(0.4)
 H19D(0.4) C17C(0.5) H17G(0.5) H17H(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18E,H18F), C18(H18G,H18H), C19(H19E,H19F), C17A(H17A,H17B), C17A(H17C,
 H17D), C17(H17E,H17F), C18A(H18A,H18B), C19A(H19A,H19B), C18B(H18C,H18D),
 C19B(H19C,H19D), C17C(H17G,H17H)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C15(H15), C16(H16), C15A(H15A), C16A(H16A), C13A(H13A),
 C12A(H12A)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C1(H1A,H1B,H1C), C20(H20G,H20H,H20I),
 C1A(H1AA,H1AB,H1AC), C20A(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_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
;