TBAB-catalyzed cascade reactions: facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes
Mishra, Kalpana; Singh, Jay Bahadur; Gupta, Tanu; Singh, Radhey M.; Organic Chemistry Frontiers 4 (2017) 1926–; doi:10.1039/C7QO00273D

data_1553780
_publ_section_title
;
 TBAB-catalyzed cascade reactions: facile synthesis of
 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via
 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1926
_journal_paper_doi               10.1039/C7QO00273D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C19 H11 Cl F3 N O'
_chemical_formula_sum            'C19 H11 Cl F3 N O'
_chemical_formula_weight         361.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-09 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.995(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5265(8)
_cell_length_b                   18.9585(9)
_cell_length_c                   11.1154(5)
_cell_measurement_reflns_used    3960
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.7
_cell_volume                     3166.0(3)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_measurement_method       Omega-Scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         2.711
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0559P)^2^+2.2774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3027
_reflns_number_total             3960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00273d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1553780
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              4942
_shelx_hkl_checksum              86083