Metal free direct formation of various substituted pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization
Tber, Z.; Hiebel, M.-A.; Allouchi, H.; El Hakmaoui, A.; Akssira, M.; Guillaumet, G.; Berteina-Raboin, S.; RSC Adv. 5 (2015) 35201–; doi:10.1039/C5RA03703D

data_7220200
_publ_section_title
;
 Metal free direct formation of various substituted
 pyrido[2&#x2032;,1&#x2032;:2,3]imidazo[4,5-c]isoquinolin-5-amines and
 their further functionalization
;
_journal_issue                   44
_journal_name_full               'RSC Adv.'
_journal_page_first              35201
_journal_paper_doi               10.1039/C5RA03703D
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C23 H14 F3 N4 O'
_chemical_formula_weight         419.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-02-02T14:37:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-02-02 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.73(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.065(3)
_cell_length_b                   5.4072(11)
_cell_length_c                   17.347(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     4038(2)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.01
_diffrn_orient_matrix_UB_12      0
_diffrn_orient_matrix_UB_13      0
_diffrn_orient_matrix_UB_21      0
_diffrn_orient_matrix_UB_22      0.01
_diffrn_orient_matrix_UB_23      0
_diffrn_orient_matrix_UB_31      0
_diffrn_orient_matrix_UB_32      0
_diffrn_orient_matrix_UB_33      0.01
_diffrn_radiation_monochromator  'graded mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7600
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.3147
_refine_ls_R_factor_gt           0.1407
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3764
_refine_ls_wR_factor_ref         0.4492
_reflns_number_gt                1387
_reflns_number_total             4120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra03703d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7220200
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.997