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_4035671
_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         'C21 H13 Cl2 N'
_chemical_formula_sum            'C21 H13 Cl2 N'
_chemical_formula_weight         350.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                115.42(3)
_cell_angle_beta                 92.81(3)
_cell_angle_gamma                96.49(3)
_cell_formula_units_Z            4
_cell_length_a                   9.1673(18)
_cell_length_b                   13.916(3)
_cell_length_c                   14.952(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                     1701.6(8)
_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 0.955
_diffrn_measured_fraction_theta_max 0.952
_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  0.0510
_diffrn_reflns_av_unetI/netI     0.1756
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11546
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.573
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.998
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.460
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.460
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1882
_reflns_number_total             6030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02261_si_002.cif
_cod_data_source_block           az2
_cod_original_cell_volume        1701.7(7)
_cod_database_code               4035671
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.945
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              7927
_shelx_hkl_checksum              12473