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_4511893
_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         'C19 H17 N3 O2, H2 O'
_chemical_formula_sum            'C19 H19 N3 O3'
_chemical_formula_weight         337.37
_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             2013-04-19
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.19 svn.r2675, GUI svn.r4458)
;
_cell_angle_alpha                102.747(7)
_cell_angle_beta                 100.480(8)
_cell_angle_gamma                106.662(8)
_cell_formula_units_Z            2
_cell_length_a                   8.7561(9)
_cell_length_b                   9.8293(8)
_cell_length_c                   10.7014(9)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0690
_cell_measurement_theta_min      4.3800
_cell_volume                     830.46(14)
_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      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9677
_diffrn_measured_fraction_theta_max 0.9677
_diffrn_measurement_details
;
  1 omega  -11.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -41.0000   26.0000 26

  2 omega   -7.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -41.0000 -179.0000 25

  3 omega   19.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -41.0000   26.0000 38

  4 omega   48.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   41.0000    0.0000 27

  5 omega  -12.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   41.0000  179.0000 28

  6 omega -116.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -41.0000    0.0000 93

  7 omega  -51.00   24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   41.0000  -26.0000 75

  8 omega   85.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   41.0000    0.0000 80

  9 omega   65.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -41.0000 -179.0000 25

 10 omega   46.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -41.0000   26.0000 49

 11 omega  148.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   41.0000  153.0000 27

 12 omega   89.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   41.0000  153.0000 45

 13 omega   25.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048 -125.0000  150.0000 73

 14 omega   42.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   41.0000  153.0000 25

 15 omega -113.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -41.0000 -153.0000 81

 16 omega   26.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -180.0000 82

 17 omega   61.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   60.0000 48

 18 omega   82.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   90.0000 95

 19 omega   35.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000 -150.0000 41

 20 omega   50.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -77.0000 -120.0000 25

 21 omega   33.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  150.0000 57

 22 omega  146.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  125.0000  -90.0000 26

 23 omega   56.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 53

 24 omega   26.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -30.0000 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1762807000
_diffrn_orient_matrix_UB_12      -0.0306038000
_diffrn_orient_matrix_UB_13      0.0176337000
_diffrn_orient_matrix_UB_21      0.0460816000
_diffrn_orient_matrix_UB_22      0.1646011000
_diffrn_orient_matrix_UB_23      0.0767065000
_diffrn_orient_matrix_UB_31      -0.0549876000
_diffrn_orient_matrix_UB_32      0.0344267000
_diffrn_orient_matrix_UB_33      -0.1311516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5770
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.950
_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            gold
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.1937
_exptl_crystal_size_mid          0.0868
_exptl_crystal_size_min          0.0643
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0728P)^2^+0.2105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                2136
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            co5000695_si_002.cif
_cod_data_source_block           evde_ugent003b
_cod_depositor_comments
'Adding full bibliography for 4511893--4511894.cif.'
_cod_database_code               4511893
_chemical_oxdiff_formula         'C19 H16 N3 O2'
_reflns_odcompleteness_completeness 96.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H1-N1
 0.86 with sigma of 0.01
 H3C-O3
 0.82 with sigma of 0.01
 H3D-O3
 0.82 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;