Catalytic enantioselective addition of aromatic amines to enones: synthesis of optically active β-amino acid derivatives
Zhuang, Wei; Hazell, Rita G.; Jørgensen, Karl Anker; Chemical Communications  (2001) 1240–; doi:10.1039/b103334b

data_7115009
_publ_contact_author             'Prof Karl Anker Jorgensen'
_publ_section_title
;
 Catalytic enantioselective addition of aromatic amines to enones:
 synthesis of optically active \b-amino acid derivatives
;
_journal_issue                   14
_journal_name_full               'Chemical Communications'
_journal_page_first              1240
_journal_paper_doi               10.1039/b103334b
_journal_year                    2001
_chemical_formula_sum            'C19 H23 N2 O'
_chemical_formula_weight         296.42
_chemical_name_systematic
;                                   
(S)-(Methyl-phenyl-amino)-N-((S)-1-phenyl-ethyl)-butyramide
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.329(1)
_cell_length_b                   10.329(1)
_cell_length_c                   28.108(4)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.3
_cell_measurement_theta_min      2.4
_cell_volume                     2597.0(5)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;                                   
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL                     
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;                                   
SIR97 (Altomare et al., 1997 ), KRYSTAL                            
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_max 100
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29407
_diffrn_reflns_reduction_process 29407
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.34(6)
_refine_diff_density_min         -0.43(6)
_refine_ls_extinction_coef       282(41)
_refine_ls_extinction_method
;                                   
Type 1 Lorentzian isotropic (Becker and Coppens, 1974)           
;
_refine_ls_goodness_of_fit_ref   1.38
_refine_ls_hydrogen_treatment    calculated
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;                                   
w== 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.052
_reflns_number_gt                1824
_reflns_number_total             5067
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            b103334b.txt
_cod_data_source_block           wei8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

data name '_exptl_aabsorpt_process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        2597(1)
_cod_original_sg_symbol_H-M      'P 6(5)'
_cod_original_formula_sum        C19H23N2O
_cod_database_code               7115009