Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
Donohoe, Timothy J.; O'Riordan, Timothy J C; Peifer, Manuel; Jones, Christopher R.; Miles, Timothy J.; Organic letters 14 (2012) 5460–5463; doi:10.1021/ol302541j

data_1508719
_publ_section_title
;
 Asymmetric synthesis of the fully elaborated pyrrolidinone core of
 oxazolomycin A.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5460
_journal_page_last               5463
_journal_paper_doi               10.1021/ol302541j
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        syn
_chemical_formula_moiety         'C33 H49 N1 O6 Si1'
_chemical_formula_sum            'C33 H49 N O6 Si'
_chemical_formula_weight         583.84
_chemical_melting_point          ?
_chemical_name_systematic
'(2S,3S,4S)-tert-butyl 3-allyl-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-2-((methoxymethoxy)methyl)-4-methylpyrrolidine-1-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-04-08
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 115.0630(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3589(2)
_cell_length_b                   30.3196(5)
_cell_length_c                   11.4539(2)
_cell_measurement_reflns_used    5907
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     3258.69(10)
_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 0.986
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10209
_diffrn_reflns_theta_full        25.229
_diffrn_reflns_theta_max         26.839
_diffrn_reflns_theta_min         2.075
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.56
_refine_ls_extinction_coef       110(60)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9110
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.0009494
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.97P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1214
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1214
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              38
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4171
_reflns_number_total             6711
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      17.00
_oxford_refine_ls_r_factor_ref   0.0983
_oxford_refine_ls_scale          0.2548(2)
_oxford_reflns_number_all        6680
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title allylic
_cod_data_source_file            ol302541j_si_002.cif
_cod_data_source_block           13
_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.

'_symmetry_cell_setting' value
'Monoclinic' changed to 'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C33 H49 N1 O6 Si1'
_cod_database_code               1508719