On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters.
Davies, Stephen G.; Foster, Emma M.; Frost, Aileen B.; Lee, James A.; Roberts, Paul M.; Thomson, James E.; Organic & biomolecular chemistry 10 (2012) 6186–6200; doi:10.1039/c2ob25099c

data_7152458
_publ_section_title
;
 On the origins of diastereoselectivity in the conjugate additions of the
 antipodes of lithium N-benzyl-(N-\a-methylbenzyl)amide to enantiopure
 cis- and trans-dioxolane containing \a,\b-unsaturated esters.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6186
_journal_page_last               6200
_journal_paper_doi               10.1039/c2ob25099c
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration (S,S,S)
_chemical_formula_moiety         'C16 H31 N1 O4'
_chemical_formula_sum            'C16 H31 N O4'
_chemical_formula_weight         301.43
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 105.8953(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1832(6)
_cell_length_b                   5.8375(2)
_cell_length_c                   14.5119(4)
_cell_measurement_reflns_used    2239
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1807.36(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.987
_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  0.030
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4052
_diffrn_reflns_theta_full        26.856
_diffrn_reflns_theta_max         27.404
_diffrn_reflns_theta_min         5.410
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9701
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.0003891
_refine_ls_shift/su_mean         0.0000463
_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:
76.2 128. 79.5 34.3 8.30
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1210
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1210
_reflns_limit_h_max              27
_reflns_limit_h_min              -28
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2088
_reflns_number_total             2239
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.20
_oxford_diffrn_Wilson_scale      1.70
_oxford_refine_ls_r_factor_ref   0.0494
_oxford_refine_ls_scale          0.748(4)
_oxford_reflns_number_all        2239
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c2ob25099c.txt
_cod_data_source_block           57
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_formula_sum        'C16 H31 N1 O4'
_cod_database_code               7152458