Asymmetric Syntheses of APTO and AETD: the β-Amino Acid Fragments within Microsclerodermins C, D, and E
Stephen G. Davies; Ai M. Fletcher; Emma M. Foster; James A. Lee; Paul M. Roberts; James E. Thomson; Journal of Organic Chemistry 78 (2013) 2500–2510; doi:10.1021/jo302731m

data_4028052
_publ_contact_author             'Stephen G. Davies'
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 Asymmetric Syntheses of APTO and AETD: the \b-Amino Acid Fragments within
 Microsclerodermins C, D, and E
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2500
_journal_page_last               2510
_journal_paper_doi               10.1021/jo302731m
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H33 N5 O9 S1'
_chemical_formula_sum            'C23 H33 N5 O9 S'
_chemical_formula_weight         555.61
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.009(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9357(5)
_cell_length_b                   5.3382(5)
_cell_length_c                   25.560(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1355.7(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6908
_diffrn_reflns_theta_full        25.313
_diffrn_reflns_theta_max         76.705
_diffrn_reflns_theta_min         3.458
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.81
_refine_diff_density_min         -0.58
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.17(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6879
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          0.0003959
_refine_ls_shift/su_mean         0.0000177
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 5.74P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2431
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2431
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              5
_reflns_limit_k_min              -6
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                5890
_reflns_number_total             2990
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.14
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0996
_oxford_refine_ls_scale          8.9(5)
_oxford_reflns_number_all        6879
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            jo302731m_si_001_3.cif
_cod_data_source_block           40
_cod_original_cell_volume        1355.67(19)
_cod_original_formula_sum        'C23 H33 N5 O9 S1'
_cod_database_code               4028052