One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.
Barber, David M.; Duriš, Andrej; Thompson, Amber L.; Sanganee, Hitesh J.; Dixon, Darren J.; ACS catalysis 4 (2014) 634–638; doi:10.1021/cs401008v

data_4509833
_publ_section_title
;
 One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the
 Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold
 Catalysis.
;
_journal_issue                   2
_journal_name_full               'ACS catalysis'
_journal_page_first              634
_journal_page_last               638
_journal_paper_doi               10.1021/cs401008v
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O6'
_chemical_formula_sum            'C22 H24 N2 O6'
_chemical_formula_weight         412.44
_chemical_melting_point          ?
_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_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-06-21
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.82410(10)
_cell_length_b                   9.82410(10)
_cell_length_c                   37.0024(7)
_cell_measurement_reflns_used    20831
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     3092.76(7)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            42763
_diffrn_reflns_theta_full        76.225
_diffrn_reflns_theta_max         76.225
_diffrn_reflns_theta_min         5.199
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1308.000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 1998 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     301
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.0055110
_refine_ls_shift/su_mean         0.0004997
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.38P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0661
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0661
_reflns_limit_h_max              0
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              46
_reflns_limit_l_min              -41
_reflns_number_gt                4020
_reflns_number_total             4199
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.98
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0282
_oxford_refine_ls_scale          5.63(7)
_oxford_reflns_number_all        4186
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 005djd13
_cod_data_source_file            cs401008v_si_002.cif
_cod_data_source_block           4k
_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.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

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 
;
_cod_original_sg_symbol_Hall     'P 65 '
_cod_original_sg_symbol_H-M      'P 65 '
_cod_database_code               4509833
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
EQUIV PART(2001,OCC) PART(2002,OCC) 
WEIGHT -1 PART(2002,OCC) 
RIDE C(5,X'S,U'S) C(105,X'S,U'S) 
RIDE C(4,U'S) C(104,U'S) 
RIDE C(21,U'S) C(121,U'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) H   (1042,X'S) 
RIDE C   ( 106,X'S) H   (1061,X'S) 
RIDE C   ( 107,X'S) H   (1071,X'S) 
RIDE C   ( 108,X'S) H   (1081,X'S) 
RIDE C   ( 109,X'S) H   (1091,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 121,X'S) H   (1211,X'S) H   (1212,X'S) H   (1213,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
SAME  C(4)  C(5)  C(6)  C(7)  C(8)  C(9)  C(10)  AND 
CONT  C(4)  C(5)  C(10)  C(9)  C(8)  C(7)  C(6)  AND 
CONT  C(104)  C(105)  C(106)  C(107)  C(108)  C(109)  C(110)  AND 
CONT  C(104)  C(105)  C(110)  C(109)  C(108)  C(107)  C(106) 
SIMU  0.01  O(3)  C(4)  C(5)  C(6)  C(7)  C(8)  C(9)  C(10)  AND 
CONT  O(3)  C(4)  C(5)  C(10)  C(9)  C(8)  C(7)  C(6)  AND 
CONT  O(3)  C(104)  C(105)  C(106)  C(107)  C(108)  C(109)  C(110)  AND 
CONT  O(3)  C(104)  C(105)  C(110)  C(109)  C(108)  C(107)  C(106) 
DELU  0.01  O(3)  C(4)  C(5)  C(6)  C(7)  C(8)  C(9)  C(10)  AND 
CONT  O(3)  C(4)  C(5)  C(10)  C(9)  C(8)  C(7)  C(6)  AND 
CONT  O(3)  C(104)  C(105)  C(106)  C(107)  C(108)  C(109)  C(110)  AND 
CONT  O(3)  C(104)  C(105)  C(110)  C(109)  C(108)  C(107)  C(106) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.08000 = O(20) TO C(21) 
U(IJ) .0, 0.08000 = O(20) TO C(121) 
U(IJ) .0, 0.02000 = C(21) TO C(121) 
VIBR .0, 0.00200 = O(20) TO C(21) 
VIBR .0, 0.00500 = C(21) TO C(19) 
VIBR .0, 0.00200 = O(20) TO C(121) 
VIBR .0, 0.00500 = C(121) TO C(19) 
END                                                                             
;