N-heterocyclic carbene-catalyzed stereoselective cascade reaction: synthesis of functionalized tetrahydroquinolines.
Zhang, Hai-Rui; Dong, Zhen-Wen; Yang, Yu-Jie; Wang, Ping-Luan; Hui, Xin-Ping; Organic letters 15 (2013) 4750–4753; doi:10.1021/ol4024985

data_1512388
_publ_section_title
;
 N-heterocyclic carbene-catalyzed stereoselective cascade reaction:
 synthesis of functionalized tetrahydroquinolines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4750
_journal_page_last               4753
_journal_paper_doi               10.1021/ol4024985
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Br N O2'
_chemical_formula_sum            'C24 H18 Br N O2'
_chemical_formula_weight         432.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2013-03-29
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.303(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.2930(3)
_cell_length_b                   8.7810(6)
_cell_length_c                   20.7367(10)
_cell_measurement_reflns_used    1470
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4770
_cell_measurement_theta_min      3.7460
_cell_volume                     963.55(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.6718
_diffrn_measurement_details
;
  1 omega   -2.00   27.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  -90.0000 29

  2 omega    7.00   45.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000   30.0000 38

  3 omega   15.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000 -120.0000 75

  4 omega  -15.00   38.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000    0.0000 53

  5 omega    1.00   45.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000   30.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0146996000
_diffrn_orient_matrix_UB_12      0.0745203000
_diffrn_orient_matrix_UB_13      -0.0125983000
_diffrn_orient_matrix_UB_21      -0.0333174000
_diffrn_orient_matrix_UB_22      -0.0271502000
_diffrn_orient_matrix_UB_23      -0.0312530000
_diffrn_orient_matrix_UB_31      -0.1290367000
_diffrn_orient_matrix_UB_32      0.0154201000
_diffrn_orient_matrix_UB_33      0.0058231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4011
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0280P)^2^+1.0546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2468
_reflns_number_total             3034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4024985_si_002.cif
_cod_data_source_block           zhanghairui0328
_cod_database_code               1512388
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H10 of C10, H13 of C13, H14 of C14, H15 of C15, H16 of C16, H22 of C22, H21
  of C21, H17 of C17, H8 of N8, H2 of C2, H3 of C3, H4 of C4, H5 of C5, H7 of
  C7, H8A of C8, H9 of C9, H25 of C25, H24 of C24
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8A), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C25(H25)
;