Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines
Likhar, Pravin R.; Subhas, Madavu Salian; Roy, Sarabindu; Kantam, Mannepalli Lakshmi; Sridhar, Balasubramanian; Seth, Ratanesh Kumar; Biswas, Sukla; Organic & Biomolecular Chemistry 7 (2009) 85–93; doi:10.1039/b815398a

data_7150555
_publ_section_title
;
 Synthesis of highly substituted 2-perfluoroalkyl quinolines by
 electrophilic iodocyclization of perfluoroalkyl propargyl
 imines/amines
;
_journal_issue                   1
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              85
_journal_page_last               93
_journal_paper_doi               10.1039/b815398a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C18 H13 F3 I N O2'
_chemical_formula_sum            'C18 H13 F3 I N O2'
_chemical_formula_weight         459.19
_chemical_name_systematic
3-Iodo-6-methoxy-4-(p-methoxyphenyl)-2-trifluoromethyl)quinoline
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.100(4)
_cell_angle_beta                 95.726(4)
_cell_angle_gamma                110.042(3)
_cell_formula_units_Z            2
_cell_length_a                   8.995(2)
_cell_length_b                   10.147(2)
_cell_length_c                   11.016(3)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.28
_cell_volume                     880.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7577
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.2514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                2691
_reflns_number_total             2973
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b815398a.txt
_cod_data_source_block           aq35m
_cod_database_code               7150555