Chemistry of Heterocyclic Ketene Aminals: Construction of Imidazo(pyrido)[1,2-a]pyridines and Imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-Catalyzed Tandem Annulations
Ming Li; Zhong-Min Zhou; Li-Rong Wen; Zhong-Xuan Qiu; Journal of Organic Chemistry 76 (2011) 3054–3063; doi:10.1021/jo102167g

data_4026228
_publ_section_title
;
 Chemistry of Heterocyclic Ketene Aminals: Construction of
 Imidazo(pyrido)[1,2-a]pyridines and
 Imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-Catalyzed Tandem
 Annulations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3054
_journal_page_last               3063
_journal_paper_doi               10.1021/jo102167g
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C18 H18 Cl2 N2 O2'
_chemical_formula_sum            'C18 H18 Cl2 N2 O2'
_chemical_formula_weight         365.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.367(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.300(4)
_cell_length_b                   9.767(2)
_cell_length_c                   10.675(2)
_cell_measurement_reflns_used    435
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1685.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14517
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_correction_T_min  0.8634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       platelet
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0348P)^2^+1.5697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                3559
_reflns_number_total             3844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102167g_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        1685.6(6)
_cod_database_code               4026228