Regioselective Synthesis of Fused Imidazo[1,2-a]pyrimidines via Intramolecular C-N Bond Formation/6-Endo-Dig Cycloisomerization.
Kumar, Atul; Kumar, Mukesh; Maurya, Shivam; Khanna, Ranjana S.; The Journal of organic chemistry 79 (2014) 6905–6912; doi:10.1021/jo5007762

data_4029808
_publ_section_title
;
 Regioselective Synthesis of Fused Imidazo[1,2-a]pyrimidines via
 Intramolecular C-N Bond Formation/6-Endo-Dig Cycloisomerization.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6905
_journal_page_last               6912
_journal_paper_doi               10.1021/jo5007762
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C22 H14 Cl N3'
_chemical_formula_weight         355.81
_space_group_IT_number           14
_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                 92.573(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9422(5)
_cell_length_b                   19.0885(10)
_cell_length_c                   11.2298(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1700.77(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.844
_diffrn_measured_fraction_theta_max 0.844
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7001
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.235
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0004(8)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.2941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                2496
_reflns_number_total             3870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5007762_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4029808.cif.'
_cod_database_code               4029808