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_7150556
_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         'C16 H9 F3 I N O'
_chemical_formula_sum            'C16 H9 F3 I N O'
_chemical_formula_weight         415.14
_chemical_name_systematic
3-Iodo-4-phenyl-2-trifluoromethyl-1-aza-spiro[4.5]deca-1,3,6,9-tetraen-8-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.871(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5479(6)
_cell_length_b                   18.4740(19)
_cell_length_c                   14.5807(15)
_cell_measurement_reflns_used    6659
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.62
_cell_volume                     1472.3(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13503
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.80
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0214P)^2^+1.3746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0552
_reflns_number_gt                2502
_reflns_number_total             2584
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b815398a.txt
_cod_data_source_block           ad61m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150556