Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and N-Sulfonylaldimines.
Smith, Siobhan R.; Douglas, James; Prevet, Hugues; Shapland, Peter; Slawin, Alexandra M. Z.; Smith, Andrew D.; The Journal of organic chemistry 79 (2014) 1626–1639; doi:10.1021/jo402590m

data_4028990
_publ_section_title
;
 Isothiourea-Catalyzed Asymmetric Synthesis of \b-Lactams and \b-Amino
 Esters from Arylacetic Acid Derivatives and N-Sulfonylaldimines.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1626
_journal_page_last               1639
_journal_paper_doi               10.1021/jo402590m
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 Br N O4 S'
_chemical_formula_sum            'C23 H22 Br N O4 S'
_chemical_formula_weight         488.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.9059(13)
_cell_length_b                   13.8595(18)
_cell_length_c                   16.783(3)
_cell_measurement_reflns_used    7070
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      3.18
_cell_volume                     2304.2(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.353
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15217
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.460
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1785 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4162
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0251P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                3157
_reflns_number_total             4162
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo402590m_si_001.cif
_cod_data_source_block           17
_cod_database_code               4028990