Total Synthesis and Biological Activity of the Proposed Structure of Phaeosphaeride A
Anthoula Chatzimpaloglou; Maria P. Yavropoulou; Karien E. Rooij; Ralf Biedermann; Uwe Mueller; Stefan Kaskel; Vasiliki Sarli; Journal of Organic Chemistry 77 (2012) 9659–9667; doi:10.1021/jo301662e

data_4027649
_publ_contact_author_address
;Aristotle University of Thessaloniki
Department of Chemistry
Laboratory of Organic Chemistry
Thessaloniki 54124
Greece
;
_publ_contact_author_email       sarli@chem.auth.gr
_publ_contact_author_fax         +302310997679
_publ_contact_author_name        'Vasiliki C. Sarli'
_publ_contact_author_phone       +302310997840
_publ_section_title
;
 Total Synthesis and Biological Activity of the Proposed Structure of
 Phaeosphaeride A
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9659
_journal_page_last               9667
_journal_paper_doi               10.1021/jo301662e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C15 H23 N O5'
_chemical_formula_weight         297.34
_chemical_name_systematic
;
 Phaeosphaeride A - RRR Enantiomer
;
_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   geom
_atom_sites_solution_primary     'charge flipping'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.213(2)
_cell_length_b                   5.2040(10)
_cell_length_c                   15.962(3)
_cell_measurement_reflns_used    1550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      1.62
_cell_volume                     834.7(3)
_computing_cell_refinement       XDS
_computing_data_collection       'marCCD 1994-2002'
_computing_data_reduction        XDSCONV
_computing_molecular_graphics    'Diamond 3.2'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       '\D\f scans'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'BESSY BL MX-14.2'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.88561
_diffrn_reflns_av_R_equivalents  0.1150
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7577
_diffrn_reflns_theta_full        31.98
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.0540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.2191
_reflns_number_gt                1079
_reflns_number_total             1677
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo301662e_si_002.cif
_cod_data_source_block           publication_text
_cod_database_code               4027649