Synthesis of Quinolines and Pyrido[3,2- g or 2,3- g]quinolines Catalyzed by Heterogeneous Propylphosphonium Tetrachloroindate Ionic Liquid.
Azizi, Mahboobeh; Nasr-Esfahani, Mahboobeh; Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Kia, Reza; The Journal of organic chemistry 83 (2018) 14743–14750; doi:10.1021/acs.joc.8b02261

data_4035670
_publ_section_title
;
 Synthesis of Quinolines and Pyrido[3,2- g or 2,3- g]quinolines Catalyzed
 by Heterogeneous Propylphosphonium Tetrachloroindate Ionic Liquid.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14743
_journal_page_last               14750
_journal_paper_doi               10.1021/acs.joc.8b02261
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 Cl F N O2'
_chemical_formula_sum            'C17 H11 Cl F N O2'
_chemical_formula_weight         315.72
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.500(3)
_cell_length_b                   16.914(3)
_cell_length_c                   14.059(3)
_cell_measurement_reflns_used    546
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.45
_cell_volume                     2920.2(11)
_computing_cell_refinement       'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL, PLATON (Spek, 2009)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'stoe ipds 2t'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17585
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.288
_diffrn_reflns_theta_min         2.700
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'mulabs in platon'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.998
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0669P)^2^+0.1468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2644
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02261_si_003.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035670
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.696
_shelx_estimated_absorpt_t_max   0.862
_shelx_res_checksum              83029
_shelx_hkl_checksum              14502