Prochiral Alkyl-aminomethyl Ketones as Convenient Precursors for Efficient Synthesis of Chiral (2,3,5)- Tri-substitued Pyrrolidines via an Organo-Catalysed Tandem Reaction
Song, Yuming; Li, Ke; Shu, Tao; Xie, Yamei; Zhang, Yixin; Qu, Jingping; RSC Adv.  (2016) –; doi:10.1039/C6RA10153D

data_7225396
_publ_section_title
;
 Prochiral Alkyl-aminomethyl Ketones as Convenient Precursors for
 Efficient Synthesis of Chiral (2,3,5)- Tri-substitued Pyrrolidines via an
 Organo-Catalysed Tandem Reaction
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10153D
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H22.5 N O4.5 S'
_chemical_formula_weight         368.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.156(3)
_cell_length_b                   17.874(5)
_cell_length_c                   20.771(6)
_cell_measurement_reflns_used    1843
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.175
_cell_measurement_theta_min      2.268
_cell_volume                     3770.5(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21290
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9450
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'transparent white'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                4203
_reflns_number_total             6643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra10153d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        3770.6(18)
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_original_formula_sum        'C19 H22.50 N O4.50 S'
_cod_database_code               7225396