A novel annelation to quinolines and isoquinolines under Friedel–Crafts conditions: a one-step synthesis of functionalized pyridoquinolines and pyridoisoquinolines
Mahato, Shashi B.; Garai, Subhadra; Weber, Manuela; Luger, Peter; Journal of the Chemical Society, Perkin Transactions 1  (2000) 2898–; doi:10.1039/b004444j

data_7213393
_publ_contact_author
;
     Prof. Peter Luger
     Institut f\"ur Chemie/Kristallographie
     Freie Universit\"at
     Fachbereich Biologie, Chemie, Pharmazie
     Takustr. 6
     14195 Berlin
     Germany
;
_publ_section_title
;
 A novel annelation to quinolines and isoquinolines under Friedel--Crafts
 conditions: a one-step synthesis of functionalized pyridoquinolines and
 pyridoisoquinolines
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2898
_journal_paper_doi               10.1039/b004444j
_journal_year                    2000
_chemical_formula_moiety         'C14 H9 Cl2 N1 O2'
_chemical_formula_sum            'C14 H9 Cl2 N O2'
_chemical_formula_weight         294.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0(1)
_cell_angle_beta                 92.8(1)
_cell_angle_gamma                90.0(1)
_cell_formula_units_Z            8
_cell_length_a                   22.123(3)
_cell_length_b                   7.040(1)
_cell_length_c                   15.937(3)
_cell_measurement_reflns_used    105
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      20
_cell_volume                     2479.2(7)
_computing_cell_refinement       'STOE software'
_computing_data_collection       'STOE software'
_computing_data_reduction        'Stoe-routine REDUC'
_computing_molecular_graphics
;
SCHAKAL88 (Keller, 1988)
;
_computing_publication_material
;
SHELXL-93_ACTA (Sheldrick, 1993)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1992)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Stoe four circle diffractometer, microVAX controlled
;
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  no
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4608
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         4.00
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.687
_exptl_absorpt_correction_T_max  0.4826
_exptl_absorpt_correction_T_min  0.1953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(Hall, 1982)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.00104(17)
_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   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.9342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                3690
_reflns_number_total             4434
_reflns_threshold_expression     >4sigma(Fo)
_cod_data_source_file            b004444jsup1.cif
_cod_data_source_block           qn1_abs
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C14 H9 Cl2 N1 O2'
_cod_database_code               7213393