Amine-Mediated Transimination and Aromatization-Triggered Domino Reaction in the Synthesis of Polyfunctionalized 4-Aminoquinolines.
Song, Runzhe; Han, Zhaomeng; He, Qiuqin; Fan, Renhua; Organic letters 18 (2016) 5328–5331; doi:10.1021/acs.orglett.6b02643

data_1555844
_publ_section_title
;
 Amine-Mediated Transimination and Aromatization-Triggered Domino Reaction
 in the Synthesis of Polyfunctionalized 4-Aminoquinolines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5328
_journal_page_last               5331
_journal_paper_doi               10.1021/acs.orglett.6b02643
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C21 H22 N2'
_chemical_formula_weight         302.40
_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-2013
_cell_angle_alpha                74.645(2)
_cell_angle_beta                 86.219(2)
_cell_angle_gamma                69.2150(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8501(10)
_cell_length_b                   9.6086(11)
_cell_length_c                   10.7805(12)
_cell_measurement_reflns_used    4797
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.35
_cell_volume                     826.09(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7914
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.720
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.034(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1183P)^2^+0.0997P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3314
_reflns_number_total             3808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02643_si_002.cif
_cod_data_source_block           mo_40326b
_cod_database_code               1555844
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-2
_shelx_res_checksum              31368
_shelx_hkl_checksum              9937