Conjugate Additions to Phenylglycinol-Derived Unsaturated δ-Lactams. Enantioselective Synthesis of Uleine Alkaloids
Amat, Mercedes; Pérez, Maria; Llor, Núria; Escolano, Carmen; Luque, F. Javier; Molins, Elies; Bosch, Joan; The Journal of Organic Chemistry 69 (2004) 8681–8693; doi:10.1021/jo0487101

data_4028890
_publ_section_title
;
 Conjugate Additions to Phenylglycinol-Derived Unsaturated
 \d-Lactams. Enantioselective Synthesis of Uleine Alkaloids
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   25
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              8681
_journal_page_last               8693
_journal_paper_doi               10.1021/jo0487101
_journal_volume                  69
_journal_year                    2004
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H25 N1 O2 S2'
_chemical_formula_sum            'C46 H50 N2 O4 S4'
_chemical_formula_weight         823.12
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2004-03-26T18:13:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.84(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.011(6)
_cell_length_b                   8.762(4)
_cell_length_c                   18.586(6)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      16.12
_cell_measurement_theta_min      12.25
_cell_measurement_wavelength     0.71073
_cell_volume                     2111.3(15)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.048052
_diffrn_orient_matrix_UB_12      0.015398
_diffrn_orient_matrix_UB_13      -0.077987
_diffrn_orient_matrix_UB_21      -0.073619
_diffrn_orient_matrix_UB_22      0.034403
_diffrn_orient_matrix_UB_23      0.02741
_diffrn_orient_matrix_UB_31      0.10602
_diffrn_orient_matrix_UB_32      0.090277
_diffrn_orient_matrix_UB_33      0.036453
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3875
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.84
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_correction_T_min  0.8833
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'truncated pyramid'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.8237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                3239
_reflns_number_total             3362
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4021074
_cod_data_source_file            jo0487101sup4.cif
_cod_data_source_block           jb38
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-11

 Marked entry as a duplicate of entry 4021074.

 Antanas Vaitkus,
 2019-10-11
;
_cod_database_code               4028890
_diffrn_standards_decay_corr_max 1
_diffrn_standards_decay_corr_min 1