Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives
Xiaoming Zeng; Guido D. Frey; Rei Kinjo; Bruno Donnadieu; Guy Bertrand; Journal of the American Chemical Society 131 (2009) 8690–8696; doi:10.1021/ja902051m

data_4104578
_publ_contact_author             'Prof G. Bertrand'
_publ_contact_author_address
;
University of California
UCR-CNRS Joint Research Lab
(UMR 2282) 
Department of Chemistry
Riverside, CA 92521 USA 
;
_publ_contact_author_email       ' guy.bertrand@ucr.edu '
_publ_section_title
;
 Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic
 (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I)
 Complex in the Three-Component Preparation of 1,2-Dihydroquinoline
 Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8690
_journal_page_last               8696
_journal_paper_doi               10.1021/ja902051m
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C21 H24.50 N'
_chemical_formula_sum            'C21 H24.5 N'
_chemical_formula_weight         290.92
_chemical_melting_point          94
_chemical_name_common
'2-ethyl-1,2 dihydro-1-methyl-4-phenyl-2-propylquinoline '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.700(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7579(17)
_cell_length_b                   12.115(2)
_cell_length_c                   14.384(3)
_cell_measurement_reflns_used    4106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8455
_cell_measurement_theta_min      2.2085
_cell_volume                     1680.9(5)
_computing_cell_refinement       'Bruker  APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13906
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, version 2004/1, Bruker (2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.003(3)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4288
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1037P)^2^+1.0383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.1997
_reflns_number_gt                3386
_reflns_number_total             4288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja902051m_si_001_2.cif
_cod_data_source_block           11a
_cod_original_cell_volume        1680.8(5)
_cod_original_formula_sum        'C21 H24.50 N'
_cod_database_code               4104578