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_7063805
_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         'C12 H12 N4'
_chemical_formula_sum            'C12 H12 N4'
_chemical_formula_weight         212.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6736(4)
_cell_length_b                   7.4873(4)
_cell_length_c                   22.8768(14)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.3440
_cell_measurement_theta_min      2.9730
_cell_volume                     1143.09(12)
_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 0.997
_diffrn_measured_fraction_theta_max 0.989
_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    -83.00 -35.00   1.00   45.00    --  -19.06 178.00 150.00   48
  2  \w    -33.00  43.00   1.00   45.00    --   21.56 -77.00 150.00   76
;
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            3282
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.863
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88748
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       irregular
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0789P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.485
_reflns_Friedel_fraction_full    0.676
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                1644
_reflns_number_total             2448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00255a2.cif
_cod_data_source_block           exp_1426
_cod_depositor_comments
'Adding full bibliography for 7063804--7063806.cif.'
_cod_database_code               7063805
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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
;