Role of the Countercation in Diastereoselective Alkylations of Pyramidalized Bicyclic Serine Enolates. An Easy Approach to α-Benzylserine
Gonzalo Jiménez-Osés; Carlos Aydillo; Jesús H. Busto; María M. Zurbano; Jesús M. Peregrina; Alberto Avenoza; Journal of Organic Chemistry 72 (2007) 5399–5402; doi:10.1021/jo070656b

data_4023998
_publ_contact_author_address
;Departamento de Qu\'imica
Universidad de La Rioja, UA-CSIC
26006 Logro\~no (Spain)
;
_publ_contact_author_email       alberto.avenoza@unirioja.es
_publ_contact_author_fax         (+34)941-299-655
_publ_contact_author_name        'Alberto Avenoza'
_publ_section_title
;
 Role of the Countercation in Diastereoselective Alkylations of
 Pyramidalized Bicyclic Serine Enolates. An Easy Approach to
 \a-Benzylserine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5399
_journal_page_last               5402
_journal_paper_doi               10.1021/jo070656b
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_sum            'C20 H30 N2 O12'
_chemical_formula_weight         490.46
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4170(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3175(3)
_cell_length_b                   11.1152(3)
_cell_length_c                   11.2197(4)
_cell_measurement_reflns_used    13024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.21
_cell_volume                     1159.91(6)
_computing_cell_refinement       'Denzo and Scalepak (1997)'
_computing_data_collection       'Nonius Kappa CCD'
_computing_data_reduction        'Denzo and Scalepak (1997)'
_computing_molecular_graphics    'ORTEP III'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10432
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0515P)^2^+0.0808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                4019
_reflns_number_total             5314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070656bsi20070330_122749.cif
_cod_data_source_block           shelxl
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023998