Synthesis of the Sponge-Derived Plakortone Series of Bioactive Compounds
Patricia Y. Hayes; Sharon Chow; Fredrik Rahm; Paul V. Bernhardt; James J. De Voss; William Kitching; Journal of Organic Chemistry 75 (2010) 6489–6501; doi:10.1021/jo101224w

data_4025700
_publ_section_title
;
 Synthesis of the Sponge-Derived Plakortone Series of Bioactive Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6489
_journal_page_last               6501
_journal_paper_doi               10.1021/jo101224w
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H19 N1 O6'
_chemical_formula_structural     'C16 H19 O6 N'
_chemical_formula_sum            'C16 H19 N O6'
_chemical_formula_weight         321.32
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 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/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2002-06-24T10:00:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.334(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9300(10)
_cell_length_b                   6.9429(5)
_cell_length_c                   15.8040(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.557
_cell_measurement_theta_min      9.822
_cell_measurement_wavelength     0.71073
_cell_volume                     1638.18(19)
_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)'
_diffrn_ambient_temperature      293(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 TurboCAD4'
_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      -0.64779E-1
_diffrn_orient_matrix_UB_12      0.6669E-2
_diffrn_orient_matrix_UB_13      0.15425E-1
_diffrn_orient_matrix_UB_21      0.01396
_diffrn_orient_matrix_UB_22      -0.60083E-1
_diffrn_orient_matrix_UB_23      0.56039E-1
_diffrn_orient_matrix_UB_31      0.9701E-2
_diffrn_orient_matrix_UB_32      0.130761
_diffrn_orient_matrix_UB_33      0.24995E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1636
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.8999
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.034
_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       0.0081(16)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0675P)^2^+0.2137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                1096
_reflns_number_total             1569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101224w_si_003.cif
_cod_data_source_block           1902ph1
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4025700
_exptl_absorpt_factor_mur        0.03
_exptl_absorpt_correction_t_ave  0.9235
_diffrn_standards_decay_corr_max 1.085
_diffrn_standards_decay_corr_min 0.998