Stereoselective synthesis of highly substituted gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with chlorosulfonyl isocyanate.
Romero, Antonio; Woerpel, K. A.; Organic letters 8 (2006) 2127–2130; doi:10.1021/ol060596g

data_1505972
_publ_section_title
;
 Stereoselective synthesis of highly substituted gamma-lactams by the
 [3+2] annulation of alpha-siloxy allylic silanes with chlorosulfonyl
 isocyanate.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2127
_journal_page_last               2130
_journal_paper_doi               10.1021/ol060596g
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C18 H29 N O Si'
_chemical_formula_weight         303.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                75.358(5)
_cell_angle_beta                 83.355(5)
_cell_angle_gamma                63.325(4)
_cell_formula_units_Z            2
_cell_length_a                   8.194(2)
_cell_length_b                   8.643(3)
_cell_length_c                   14.789(4)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.26
_cell_volume                     905.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      168(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '25s frmes at 0.3 deg omega increments'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9730
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  .73
_exptl_absorpt_correction_type   'semi-empirical from equivalents'
_exptl_absorpt_process_details   'computed via SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         3.359
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.1111
_refine_ls_shift/su_max          0.086
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.11P)^2^+5.4P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3022
_refine_ls_wR_factor_ref         0.3092
_reflns_number_gt                3677
_reflns_number_total             4348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060596gsi20060311_041638.cif
_cod_data_source_block           kaw83
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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_original_sg_symbol_H-M      P-1
_cod_database_code               1505972