Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA'BC sequential four-component reaction and their application to 2-arylquinoline synthesis.
Ribelles, Pascual; Sridharan, Vellaisamy; Villacampa, Mercedes; Ramos, Ma Teresa; Menéndez, J Carlos; Organic & biomolecular chemistry 11 (2013) 569–579; doi:10.1039/c2ob26754c

data_7152768
_publ_section_title
;
 Diastereoselective, multicomponent access to
 trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA'BC
 sequential four-component reaction and their application to
 2-arylquinoline synthesis.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              569
_journal_page_last               579
_journal_paper_doi               10.1039/c2ob26754c
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C26 H30 N2'
_chemical_formula_sum            'C26 H30 N2'
_chemical_formula_weight         370.52
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-12-01 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.253(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4429(3)
_cell_length_b                   7.4627(2)
_cell_length_c                   14.1231(4)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.26
_cell_measurement_theta_min      4.24
_cell_volume                     1098.87(5)
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.860
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4866
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         4.24
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.0795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2316
_reflns_number_total             2432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26754c.txt
_cod_data_source_block           4fin
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7152768