Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium Ions Governed by Stereoelectronic Effects
Vi Tuong Tran; K. A. Woerpel; Journal of Organic Chemistry 78 (2013) 6609–6621; doi:10.1021/jo400945j

data_4028405
_publ_section_title
;
 Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium
 Ions Governed by Stereoelectronic Effects
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6609
_journal_page_last               6621
_journal_paper_doi               10.1021/jo400945j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H44 N4 O7 Si2'
_chemical_formula_weight         568.82
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                88.0590(8)
_cell_angle_beta                 89.2760(9)
_cell_angle_gamma                88.0016(9)
_cell_formula_units_Z            2
_cell_length_a                   7.0843(5)
_cell_length_b                   8.9087(6)
_cell_length_c                   24.7678(18)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.29
_cell_volume                     1561.19(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0103
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18757
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.923
_diffrn_reflns_theta_min         2.289
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9245
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 6060 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     747
_refine_ls_number_reflns         14227
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.5973P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                13387
_reflns_number_total             14227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo400945j_si_002.cif
_cod_data_source_block           kaw159
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_database_code               4028405
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2012-9
_shelx_res_checksum              15516