One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-Mannich/hydroamination cascade.
Barber, David M.; Sanganee, Hitesh J.; Dixon, Darren J.; Organic letters 14 (2012) 5290–5293; doi:10.1021/ol302459c

data_1508690
_publ_section_title
;
 One-pot catalytic enantioselective synthesis of tetrahydropyridines via a
 nitro-Mannich/hydroamination cascade.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5290
_journal_page_last               5293
_journal_paper_doi               10.1021/ol302459c
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 Cl1 N2 O4'
_chemical_formula_sum            'C17 H21 Cl N2 O4'
_chemical_formula_weight         352.82
_chemical_melting_point          ?
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-05-24
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 113.6819(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9959(2)
_cell_length_b                   7.10130(10)
_cell_length_c                   18.0983(4)
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1765.00(5)
_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 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36469
_diffrn_reflns_theta_full        26.936
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         5.142
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details 'Flack (1983), 3679 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         8017
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.0003176
_refine_ls_shift/su_mean         0.0000578
_refine_ls_structure_factor_coef Fsqd
_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: 
 20.5 29.0 14.5 3.81 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0931
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0931
_reflns_limit_h_max              17
_reflns_limit_h_min              -19
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                6403
_reflns_number_total             8017
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.94
_oxford_diffrn_Wilson_scale      2.14
_oxford_refine_ls_r_factor_ref   0.0554
_oxford_refine_ls_scale          0.7022(5)
_oxford_reflns_number_all        8017
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '004djd12 At 8:46 on 23/ 2'
_cod_data_source_file            ol302459c_si_001.cif
_cod_data_source_block           XX
_cod_depositor_comments
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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 1891 2012-01-12 08:04:46Z 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_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C17 H21 Cl1 N2 O4'
_cod_database_code               1508690
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 193,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) H   ( 413,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 463,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 473,X'S) H   ( 472,X'S) 
RIDE C   (  48,X'S) H   ( 482,X'S) H   ( 481,X'S) H   ( 483,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;