Azide-based <i>in situ</i> preparation of fused heterocyclic imines and their multicomponent reactions.
Paramonova, Polina; Lebedev, Rodion; Sokolov, Alexander; Dar'in, Dmitry; Kanov, Evgeny; Murtazina, Ramilya; Gainetdinov, Raul; Kalinin, Stanislav; Bakulina, Olga; Organic & biomolecular chemistry 22 (2024) 8328–8336; doi:10.1039/d4ob01321b

data_7160146
_publ_section_title
;
 Azide-based <i>in situ</i> preparation of fused heterocyclic imines and
 their multicomponent reactions.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8328
_journal_page_last               8336
_journal_paper_doi               10.1039/d4ob01321b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.667(C2 F3 O2), 0.667(C7 H10 N3 O2)'
_chemical_formula_sum            'C6 H6.67 F2 N2 O2.67'
_chemical_formula_weight         187.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-06-03 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.670(3)
_cell_angle_beta                 96.664(3)
_cell_angle_gamma                95.213(3)
_cell_formula_units_Z            3
_cell_length_a                   6.2237(2)
_cell_length_b                   8.6358(3)
_cell_length_c                   10.4449(4)
_cell_measurement_reflns_used    5184
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8260
_cell_measurement_theta_min      4.2450
_cell_volume                     555.14(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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     97.00 177.00   0.50    0.20    --  113.25  61.00 120.00  160
  2  \w    132.00 157.00   0.50    0.20    --  113.25  82.00 -14.00   50
  3  \w    102.00 173.00   0.50    0.20    --  113.25  45.00-150.00  142
  4  \w     74.00 110.00   0.50    0.05    --   47.38 125.00 -90.00   72
  5  \w     77.00 116.00   0.50    0.05    --   47.38 125.00-180.00   78
  6  \w    -65.00 -35.00   0.50    0.20    -- -106.00  61.00-180.00   60
  7  \w    -64.00 -38.00   0.50    0.20    -- -106.00  61.00-150.00   52
  8  \w    -17.00  27.00   0.50    0.05    --  -47.38  19.00-120.00   88
  9  \w    -25.00  26.00   0.50    0.05    --  -47.38  19.00 -60.00  102
 10  \w    -71.00 -45.00   0.50    0.20    -- -106.00  61.00 150.00   52
 11  \w    -40.00  25.00   0.50    0.05    --  -47.38  37.00 150.00  130
 12  \w     50.00 105.00   0.50    0.20    --  113.25 -77.00 -30.00  110
 13  \w     69.00  94.00   0.50    0.20    --  113.25 -77.00 -60.00   50
 14  \w     43.00  69.00   0.50    0.20    --  113.25 -61.00-150.00   52
 15  \w    -17.00  23.00   0.50    0.05    --   47.38 -19.00 -30.00   80
 16  \w     47.00  94.00   0.50    0.20    --  113.25 -77.00  60.00   94
 17  \w     45.00  71.00   0.50    0.20    --  113.25 -61.00   0.00   52
 18  \w     42.00  69.00   0.50    0.20    --  113.25 -61.00 -60.00   54
 19  \w     45.00  71.00   0.50    0.20    --  113.25 -82.00-136.00   52
 20  \w     70.00 109.00   0.50    0.20    --  113.25-125.00-120.00   78
 21  \w     42.00 109.00   0.50    0.20    --  113.25-125.00 -60.00  134
 22  \w     55.00  80.00   0.50    0.20    --  113.25-125.00  90.00   50
 23  \w     72.00  97.00   0.50    0.20    --  113.25 -94.00 150.00   50
 24  \w     78.00 104.00   0.50    0.20    --  113.25 -94.00 120.00   52
 25  \w     26.00  63.00   0.50    0.05    --   47.38 -82.00-136.00   74
 26  \w     -9.00  17.00   0.50    0.05    --   47.38 -82.00-136.00   52
 27  \w   -167.00-135.00   0.50    0.20    -- -106.00 -94.00 -30.00   64
 28  \w   -126.00 -85.00   0.50    0.20    -- -106.00 -94.00 -30.00   82
 29  \w   -175.00-126.00   0.50    0.20    -- -106.00 -45.00 -60.00   98
 30  \w   -164.00-138.00   0.50    0.20    -- -106.00 -45.00 -90.00   52
 31  \w   -132.00-106.00   0.50    0.20    -- -106.00 -45.00 -90.00   52
 32  \w   -160.00 -82.00   0.50    0.20    -- -106.00 -82.00-136.00  156
 33  \w   -177.00-146.00   0.50    0.20    -- -106.00 -15.00   0.00   62
 34  \w   -134.00 -99.00   0.50    0.20    -- -106.00 -15.00   0.00   70
 35  \w    -80.00 -52.00   0.50    0.20    -- -106.00  82.00 -14.00   56
 36  \w    -70.00 -44.00   0.50    0.20    -- -106.00 125.00  30.00   52
 37  \w   -105.00 -76.00   0.50    0.20    -- -106.00 125.00  30.00   58
 38  \w   -126.00-101.00   0.50    0.20    -- -106.00 145.00 -33.06   50
 39  \w   -101.00 -55.00   0.50    0.20    -- -106.00 125.00 -30.00   92
 40  \w    -79.00 -40.00   0.50    0.20    -- -106.00 125.00 -90.00   78
 41  \w   -112.00 -69.00   0.50    0.20    -- -106.00 125.00-120.00   86
 42  \w   -109.00 -83.00   0.50    0.20    -- -106.00 125.00 -90.00   52
 43  \w    -66.00  23.00   0.50    0.05    --  -47.38  82.00 -14.00  178
 44  \w    -70.00 -34.00   0.50    0.20    -- -106.00 125.00 120.00   72
 45  \w   -112.00 -85.00   0.50    0.20    -- -106.00 125.00 120.00   54
 46  \w   -107.00 -73.00   0.50    0.20    -- -106.00 107.00  86.79   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1074562000
_diffrn_orient_matrix_UB_12      -0.1599669000
_diffrn_orient_matrix_UB_13      0.0332317000
_diffrn_orient_matrix_UB_21      -0.1589704000
_diffrn_orient_matrix_UB_22      0.0003326000
_diffrn_orient_matrix_UB_23      -0.1245570000
_diffrn_orient_matrix_UB_31      0.1607145000
_diffrn_orient_matrix_UB_32      -0.0807190000
_diffrn_orient_matrix_UB_33      -0.0737821000
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.344
_diffrn_reflns_theta_min         4.263
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0427P)^2^+0.2591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             2297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01321b2.cif
_cod_data_source_block           048-010_pps-102
_cod_depositor_comments          'Adding full bibliography for 7160146.cif.'
_cod_database_code               7160146
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H9 N3 O2'
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.759
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.11
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N009(H00A,H00B), C00G(H00D,H00E), C00H(H00G,H00H), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00F(H00F)
;
_shelx_res_checksum              9300
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.717