Robust Synthesis of N-Sulfonylazetidine Building Blocks via Ring Contraction of α-Bromo N-Sulfonylpyrrolidinones.
Kern, Nicolas; Felten, Anne-Sophie; Weibel, Jean-Marc; Pale, Patrick; Blanc, Aurélien; Organic letters 16 (2014) 6104–; doi:10.1021/ol5029496

data_1518274
_publ_section_title
;
 Robust Synthesis of N-Sulfonylazetidine Building Blocks via Ring
 Contraction of \a-Bromo N-Sulfonylpyrrolidinones.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6104
_journal_paper_doi               10.1021/ol5029496
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H28 Br N O4 S Si'
_chemical_formula_sum            'C18 H28 Br N O4 S Si'
_chemical_formula_weight         462.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.852(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0702(6)
_cell_length_b                   12.6435(5)
_cell_length_c                   12.3450(10)
_cell_measurement_reflns_used    4913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1097.79(14)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6629
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_min         1.658
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_T_max  0.70071
_exptl_absorpt_correction_T_min  0.60802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.010(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                3190
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5029496_si_002.cif
_cod_data_source_block           ppasf140619
_cod_depositor_comments
'Adding full bibliography for 1518273--1518274.cif.'
_cod_database_code               1518274
_shelxl_version_number           2013-4
_shelx_res_checksum              10114
_shelx_hkl_checksum              24436