Enantioselective BINOL-Phosphoric Acid Catalyzed Pictet-Spengler Reactions of N-Benzyltryptamine
Nishant V. Sewgobind; Martin J. Wanner; Steen Ingemann; René de Gelder; Jan H. van Maarseveen; Henk Hiemstra; Journal of Organic Chemistry 73 (2008) 6405–6408; doi:10.1021/jo8010478

data_4023622
_publ_contact_author
;
         Prof.dr. H. Hiemstra
         Van 't Hoff Institute for Molecular Sciences
         Faculty of Science
         University of Amsterdam
         Nieuwe Achtergracht 129
         1018 WS Amsterdam
         The Netherlands
;
_publ_contact_author_email       hiemstra@science.uva.nl
_publ_contact_author_fax         '031 024 5255670'
_publ_contact_author_phone       '031 020 5255671'
_publ_section_title
;
 Enantioselective BINOL-Phosphoric Acid Catalyzed
 Pictet-Spengler Reactions of N-Benzyltryptamine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6405
_journal_page_last               6408
_journal_paper_doi               10.1021/jo8010478
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C24 H21 Br N2'
_chemical_formula_sum            'C24 H21 Br N2'
_chemical_formula_weight         417.34
_chemical_name_systematic
;
2-benzyl-1-(p-bromophenyl)-1,2,3,4-tetrahydro-beta-carboline
;
_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_date             2006-07-27
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.810(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1475(4)
_cell_length_b                   5.85050(18)
_cell_length_c                   14.4422(8)
_cell_measurement_reflns_used    174
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.830
_cell_volume                     939.03(7)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_diffrn_ambient_temperature      208(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector \f and \w scan'
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18797
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.200
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rather regular needle'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_Flack   0.048(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.039
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0445
_refine_ls_R_factor_obs          0.0445
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_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^)+(0.0049P)^2^+0.2808P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0577
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_obs         0.0524
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                3243
_reflns_number_observed          3243
_reflns_number_total             4224
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8010478-file002.cif
_cod_data_source_block           HIEM09
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (31
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (44 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023622