Direct enantioselective Brønsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids.
Holloway, Chloe A.; Muratore, Michael E.; Storer, R. Lan; Dixon, Darren J.; Organic letters 12 (2010) 4720–4723; doi:10.1021/ol101651t

data_1503178
_publ_section_title
;
 Direct enantioselective Br\/onsted acid catalyzed N-acyliminium
 cyclization cascades of tryptamines and ketoacids.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4720
_journal_page_last               4723
_journal_paper_doi               10.1021/ol101651t
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 Br1 N2 O1'
_chemical_formula_sum            'C18 H19 Br N2 O'
_chemical_formula_weight         359.27
_chemical_melting_point          ?
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-06-14
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 120.2197(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7232(4)
_cell_length_b                   6.9539(2)
_cell_length_c                   14.1450(4)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1591.39(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7601
_diffrn_reflns_theta_full        26.897
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         5.375
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.70
_refine_diff_density_min         -1.07
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.030(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9334
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.0020820
_refine_ls_shift/su_mean         0.8920991
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 2.80P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0812
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0812
_reflns_limit_h_max              20
_reflns_limit_h_min              -24
_reflns_limit_k_max              8
_reflns_limit_k_min              -9
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2808
_reflns_number_total             3391
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      26.99
_oxford_refine_ls_r_factor_ref   0.0546
_oxford_refine_ls_scale          0.19604(11)
_oxford_reflns_number_all        3391
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 001djd10
_cod_data_source_file            ol101651t_si_001.cif
_cod_data_source_block           3c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_original_formula_sum        'C18 H19 Br1 N2 O1'
_cod_database_code               1503178