Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines.
Sau, Prasenjit; Rakshit, Amitava; Modi, Anju; Behera, Ahalya; Patel, Bhisma K.; The Journal of organic chemistry 83 (2018) 1056–1064; doi:10.1021/acs.joc.7b02815

data_4033328
_publ_section_title
;
 Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon
 in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and
 Imidazo[2,1-a]isoquinolines.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1056
_journal_page_last               1064
_journal_paper_doi               10.1021/acs.joc.7b02815
_journal_volume                  83
_journal_year                    2018
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C17 H11 Cl N2'
_chemical_formula_sum            'C17 H11 Cl N2'
_chemical_formula_weight         278.73
_chemical_name_systematic        Unkown
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3293(6)
_cell_length_b                   3.9877(2)
_cell_length_c                   26.5458(16)
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      3.30
_cell_volume                     1305.14(12)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2756
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Ethylacetate and methanol solvent mixture'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0372P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1412
_reflns_number_total             1644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02815_si_002.cif
_cod_data_source_block           exp_4037
_cod_depositor_comments          'Adding full bibliography for 4033328.cif.'
_cod_database_code               4033328