Short Enantioselective Syntheses of trans-5-Alkylprolines from New Functionalized Amino Alcohols
Jeanne Alladoum; Sylvain Roland; Emmanuel Vrancken; Pierre Mangeney; Catherine Kadouri-Puchot; Journal of Organic Chemistry 73 (2008) 9771–9774; doi:10.1021/jo8014243

data_4023921
_publ_contact_author_address
; 
'Laboratoire de Chimie Organique,Equipe de Synthese Organometallique selective
(UMR 7611), Universite Pierre et Marie Curie, 4 place Jussieu,75252 
Paris cedex 05, France'
;
_publ_contact_author_email       mangeney@ccr.jussieu.fr
_publ_contact_author_fax         '+33 1 44 27 75 67'
_publ_contact_author_name        'P. Mangeney'
_publ_contact_author_phone       '+33 1 44 27 55 08'
_publ_section_title
;
 Short Enantioselective Syntheses of trans-5-Alkylprolines
 from New Functionalized Amino Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9771
_journal_page_last               9774
_journal_paper_doi               10.1021/jo8014243
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H21 N1 O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.35
_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
_audit_creation_date             07-09-14
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 98.016(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0384(10)
_cell_length_b                   5.4963(4)
_cell_length_c                   11.9439(13)
_cell_measurement_reflns_used    109
_cell_measurement_temperature    200
_cell_measurement_theta_max      22
_cell_measurement_theta_min      4
_cell_volume                     717.56(12)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_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       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7874
_diffrn_reflns_theta_full        29.399
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.445
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0925
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.008961
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 1.26 0.385 0.922 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0503
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0432
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1786
_reflns_number_total             2283
_reflns_threshold_expression     I>3.0\s(I)
_oxford_structure_analysis_title '9131420 Compound X'
_cod_data_source_file            jo8014243_si_001.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'refu' changed to
'refU' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C16 H21 N1 O2'
_cod_database_code               4023921