One-Pot Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines and Isoquinolino[3,4-b]quinoxalines via Tandem Cyclization Strategies.
Bagdasarian, Alex L.; Nguyen, Huy H.; Palazzo, Teresa A.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.; The Journal of organic chemistry 81 (2016) 3924–3928; doi:10.1021/acs.joc.6b00338

data_4036701
_publ_section_title
;
 One-Pot Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines and
 Isoquinolino[3,4-b]quinoxalines via Tandem Cyclization Strategies.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3924
_journal_page_last               3928
_journal_paper_doi               10.1021/acs.joc.6b00338
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C14 H11 N3'
_chemical_formula_sum            'C14 H11 N3'
_chemical_formula_weight         221.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3341(5)
_cell_length_b                   12.6687(11)
_cell_length_c                   14.0857(12)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      4.69
_cell_volume                     1130.30(16)
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2081
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.607
_diffrn_reflns_theta_min         4.694
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.759796
_exptl_absorpt_correction_T_min  0.569498
_exptl_absorpt_correction_type   'Multi-scan, Twinabs'
_exptl_absorpt_process_details   'TWINABS V2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       Irregular_Block1
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.802
_exptl_crystal_size_mid          0.645
_exptl_crystal_size_min          0.395
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 850 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.1538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2078
_reflns_number_total             2081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00338_si_002.cif
_cod_data_source_block           TP17TW41
_cod_database_code               4036701
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.788
_shelx_res_checksum              8945
_shelx_hkl_checksum              16324