Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst–synthesis of optically active tetrahydro-beta-carbolines.
Zhuang, Wei; Hazell, Rita G.; Jørgensen, Karl Anker; Organic & biomolecular chemistry 3 (2005) 2566–2571; doi:10.1039/b505220c

data_7150179
_publ_section_title
;
 Enantioselective Friedel-Crafts type addition of indoles to
 nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of
 optically active tetrahydro-beta-carbolines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2566
_journal_page_last               2571
_journal_paper_doi               10.1039/b505220c
_journal_volume                  3
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H25 Cl1 N2 O1'
_chemical_formula_sum            'C31 H25 Cl N2 O'
_chemical_formula_weight         476.98
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      144
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-01-24T10:45:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.0175(8)
_cell_length_b                   10.0175(8)
_cell_length_c                   21.2378(13)
_cell_measurement_reflns_used    1904
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      20.57
_cell_measurement_theta_min      2.35
_cell_measurement_wavelength     0.71073
_cell_volume                     1845.7(2)
_computing_cell_refinement       'SAINT+ (Bruker-Nonius, 2004)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT+ (Bruker-Nonius, 2004)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      225(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2 CCD-based diffractometer'
_diffrn_measurement_method       \f-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4167
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2774
_reflns_number_total             4167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b505220c.txt
_cod_data_source_block           04jowz002_0m
_cod_database_code               7150179