A (-)-Sparteine-Directed Highly Enantioselective Synthesis of Boroproline. Solid- and Solution-State Structure and Properties
Andrei S. Batsanov; Christophe Grosjean; Thorben Schütz; Andrew Whiting; Journal of Organic Chemistry 72 (2007) 6276–6279; doi:10.1021/jo0708792

data_4024099
_publ_contact_author             'Andrei S.Batsanov'
_publ_contact_author_email       a.s.batsanov@durham.ac.uk
_publ_section_title
;
 A (-)-Sparteine-Directed Highly Enantioselective Synthesis
 of Boroproline. Solid- and Solution-State Structure and Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6276
_journal_page_last               6279
_journal_paper_doi               10.1021/jo0708792
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H28 B N O4'
_chemical_formula_sum            'C23 H28 B N O4'
_chemical_formula_weight         393.27
_chemical_name_systematic
; (S)-2-{(4S,5S)-4,5-diphenyl-[1,3,2]dioxaborolan-2-yl}- 
 pyrrolidine-1-carboxylic acid tert-butyl ester 
;
_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                 91.19(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.8981(10)
_cell_length_b                   8.7698(8)
_cell_length_c                   10.9656(10)
_cell_measurement_reflns_used    6541
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.61
_cell_volume                     1047.8(2)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       '\w 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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12843
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
'undeterminable, all \Df" set to 0, Friedel equivalents merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.1624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.78
_reflns_number_gt                2716
_reflns_number_total             3156
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo0708792rom20070426_030341_2.cif
_cod_data_source_block           (S)-9
_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               4024099