Tandem [8 + 2] Cycloaddition-[2 + 6 + 2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines
Maialen Aginagalde; Yosu Vara; Ana Arrieta; Ronen Zangi; Vicente L. Cebolla; Arantzazu Delgado-Camón; Fernando P. Cossío; Journal of Organic Chemistry 75 (2010) 2776–2784; doi:10.1021/jo9022815

data_4025401
_publ_section_title
;
 Tandem [8 + 2] Cycloaddition-[2 + 6 + 2] Dehydrogenation Reactions
 Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2776
_journal_page_last               2784
_journal_paper_doi               10.1021/jo9022815
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H14 N2 O1'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-07-17T12:17:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;

2008-07-17 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2180(2)
_cell_length_b                   13.0241(4)
_cell_length_c                   18.1587(6)
_cell_measurement_reflns_used    4749
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.5043
_cell_measurement_theta_min      3.1252
_cell_measurement_wavelength     0.71073
_cell_volume                     1470.56(8)
_computing_cell_refinement
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_data_collection
;

        CrysAlis CCD, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_data_reduction
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3504
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;

  1 omega  -29.00   23.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -      -26.3472   45.0000  300.0000    0.0000    0.0000 52

  2 omega  -75.00  -25.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -      -26.3472   45.0000  210.0000    0.0000    0.0000 50

  3 omega  -22.00   75.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   45.0000  330.0000    0.0000    0.0000 97

  4 omega  -55.00   73.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  150.0000    0.0000    0.0000 128

  5 omega  -20.00    6.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   77.0000  210.0000    0.0000    0.0000 26

  6 omega  -75.00  -23.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -77.0000  270.0000    0.0000    0.0000 52

  7 omega   27.00   75.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  240.0000    0.0000    0.0000 48

  8 omega  -67.00  -17.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  300.0000    0.0000    0.0000 50

  9 omega  -67.00  -42.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  120.0000    0.0000    0.0000 25

 10 omega   50.00  108.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   45.0000  180.0000    0.0000    0.0000 58

;
_diffrn_orient_matrix_UB_11      0.0722774103
_diffrn_orient_matrix_UB_12      -0.0249061836
_diffrn_orient_matrix_UB_13      0.0242618958
_diffrn_orient_matrix_UB_21      -0.0522623831
_diffrn_orient_matrix_UB_22      0.0230784493
_diffrn_orient_matrix_UB_23      0.0304406592
_diffrn_orient_matrix_UB_31      -0.0708222913
_diffrn_orient_matrix_UB_32      -0.0424546074
_diffrn_orient_matrix_UB_33      0.0023087852
_diffrn_radiation_collimation    '1.0 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12841
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

Analytical numeric absorption correction using a multifaceted crystal

                        model based on expressions derived by R.C. Clark & J.S.

        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.8088
_exptl_crystal_size_mid          0.1875
_exptl_crystal_size_min          0.1008
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                1306
_reflns_number_total             1777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022815_si_001.cif
_cod_data_source_block           macro11
_cod_original_formula_sum        'C20 H14 N2 O1'
_cod_database_code               4025401