Acyclic Remote 1,5- and 1,4,5-Stereocontrol in the Catalytic Stereoselective Reactions of β-Lactams with Aldehydes: The Effect of the N-Methylimidazole Ligand.
Plata, Paulina; Klimczak, Urszula; Zambroń, Bartosz K; The Journal of organic chemistry 83 (2018) 14527–14552; doi:10.1021/acs.joc.8b02333

data_4035684
_publ_section_title
;
 Acyclic Remote 1,5- and 1,4,5-Stereocontrol in the Catalytic
 Stereoselective Reactions of \b-Lactams with Aldehydes: The Effect of the
 N-Methylimidazole Ligand.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14527
_journal_page_last               14552
_journal_paper_doi               10.1021/acs.joc.8b02333
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H36 O3 Si'
_chemical_formula_sum            'C22 H36 O3 Si'
_chemical_formula_weight         376.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 92.178(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.206(3)
_cell_length_b                   11.2062(16)
_cell_length_c                   10.5976(15)
_cell_measurement_reflns_used    3204
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.55
_cell_measurement_theta_min      2.30
_cell_volume                     2279.2(6)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29641
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.548
_diffrn_reflns_theta_min         2.302
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.8400
_exptl_absorpt_correction_T_min  0.5320
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0689
_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^)+(0.1415P)^2^+0.7804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2276
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_reflns_number_gt                3204
_reflns_number_total             4166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02333_si_004.cif
_cod_data_source_block           BZ_G144_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035684
_shelx_estimated_absorpt_t_min   0.532
_shelx_estimated_absorpt_t_max   0.840
_shelxl_version_number           2014-3
_shelx_res_checksum              10323
_shelx_hkl_checksum              17935