Three-Component Reaction of a 2-Aminoazine, a 2-Oxoaldehyde, and a Cyclic 1,3-Dicarbonyl Compound for the Synthesis of Imidazo[1,2-a]azine Derivatives.
Peshkov, Vsevolod A.; Peshkov, Anatoly A.; Pereshivko, Olga P.; Van Hecke, Kristof; Zamigaylo, Lali L.; Van der Eycken, Erik V.; Gorobets, Nikolay Yu; ACS combinatorial science 16 (2014) 535–542; doi:10.1021/co5000695

data_4511894
_publ_section_title
;
 Three-Component Reaction of a 2-Aminoazine, a 2-Oxoaldehyde, and a Cyclic
 1,3-Dicarbonyl Compound for the Synthesis of Imidazo[1,2-a]azine
 Derivatives.
;
_journal_issue                   10
_journal_name_full               'ACS combinatorial science'
_journal_page_first              535
_journal_page_last               542
_journal_paper_doi               10.1021/co5000695
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C14 H14 N4 O3, H2 O'
_chemical_formula_sum            'C14 H16 N4 O4'
_chemical_formula_weight         304.31
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-18
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.12 svn.r2672, GUI svn.r4458)
;
_cell_angle_alpha                88.318(6)
_cell_angle_beta                 87.011(6)
_cell_angle_gamma                63.972(9)
_cell_formula_units_Z            2
_cell_length_a                   7.7985(7)
_cell_length_b                   8.6433(8)
_cell_length_c                   11.7773(7)
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4990
_cell_measurement_theta_min      3.7450
_cell_volume                     712.35(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_details
;
  1 omega   20.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -51.0000  -23.0000 26

  2 omega   40.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   51.0000  -57.0000 25

  3 omega   -8.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -51.0000 -122.0000 75

  4 omega  -62.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   51.0000  122.0000 83

  5 omega  -38.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   51.0000   23.0000 62

  6 omega -112.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -51.0000   57.0000 93

  7 omega -115.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -51.0000  156.0000 71

  8 omega   37.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -51.0000  -23.0000 43

  9 omega   85.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   51.0000  -57.0000 66

 10 omega   37.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -51.0000 -122.0000 68

 11 omega  108.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   51.0000 -156.0000 25

 12 omega -111.00  -83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -30.0000 28

 13 omega   46.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   30.0000 37

 14 omega  117.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   90.0000 51

 15 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  150.0000 26

 16 omega   49.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   60.0000 42

 17 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   90.0000 25

 18 omega   35.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -180.0000 46

 19 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  120.0000 26

 20 omega  152.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  120.0000 26

 21 omega   45.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  150.0000 54

 22 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  120.0000 26

 23 omega   80.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   90.0000 29

 24 omega  146.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  120.0000 27

 25 omega   84.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -180.0000 92

 26 omega  119.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -60.0000 59

 27 omega  100.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   60.0000 26

 28 omega   88.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  150.0000 85

 29 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  120.0000 26

 30 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   52.0000 -157.0000 25

 31 omega  -64.00  -22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298  -57.0000 -180.0000 42

 32 omega   38.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9298 -125.0000 -120.0000 60

 33 omega -125.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   60.0000 27

 34 omega   63.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  150.0000 42

 35 omega   36.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -30.0000 26

 36 omega   76.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -90.0000 31

 37 omega   70.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -30.0000 38

 38 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -52.0000  -22.0000 25

 39 omega   74.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -150.0000 34

 40 omega   57.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000  120.0000 59
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0703259000
_diffrn_orient_matrix_UB_12      0.0795276000
_diffrn_orient_matrix_UB_13      0.1187037000
_diffrn_orient_matrix_UB_21      -0.1263993000
_diffrn_orient_matrix_UB_22      -0.0956692000
_diffrn_orient_matrix_UB_23      0.0141695000
_diffrn_orient_matrix_UB_31      0.1658304000
_diffrn_orient_matrix_UB_32      -0.1544972000
_diffrn_orient_matrix_UB_33      0.0535423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7561
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         5.70
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2803
_exptl_crystal_size_mid          0.1465
_exptl_crystal_size_min          0.0808
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.0439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2125
_reflns_number_total             2675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            co5000695_si_001.cif
_cod_data_source_block           evde_ugent002
_cod_depositor_comments
'Adding full bibliography for 4511893--4511894.cif.'
_cod_database_code               4511894
_chemical_oxdiff_formula         'C14 H13 N4 O3'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N3-H3
 0.86 with sigma of 0.01
 O4-H4A = O4-H4B
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C)
;