Ring-Expanded Bicyclic β-Lactams: A Structure-Chiroptical Properties Relationship Investigation by Experiment and Calculations
Magdalena Woźnica; Aleksandra Butkiewicz; Aneta Grzywacz; Patrycja Kowalska; Marek Masnyk; Karol Michalak; Roman Luboradzki; Filipp Furche; Holger Kruse; Stefan Grimme; Jadwiga Frelek; Journal of Organic Chemistry 76 (2011) 3306–3319; doi:10.1021/jo200171w

data_4026249
_publ_contact_author_address
;Institute of Organic Chemistry PAS
Kasprzaka 44/52
01-224 Warsaw
;
_publ_contact_author_email       frelek@icho.edu.pl
_publ_contact_author_name        'Jadwiga Frelek'
_publ_section_title
;
 Ring-Expanded Bicyclic \b-Lactams: A Structure-Chiroptical Properties
 Relationship Investigation by Experiment and Calculations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3306
_journal_page_last               3319
_journal_paper_doi               10.1021/jo200171w
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H31 N O S Si'
_chemical_formula_sum            'C16 H31 N O S Si'
_chemical_formula_weight         313.57
_chemical_name_systematic
;(7R,8S)-8-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)
-1-azabicyclo[5.2.0]nonane-9-thione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 100.819(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2558(2)
_cell_length_b                   11.0858(4)
_cell_length_c                   12.0016(4)
_cell_measurement_reflns_used    1746
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     948.21(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6218
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(12)
_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     187
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.2846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3259
_reflns_number_total             3538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200171w_si_002.cif
_cod_data_source_block           mw048
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026249