Biomimetic Synthesis of (-)-Xestospongin A, (+)-Xestospongin C, (+)-Araguspongine B and the Correction of Their Absolute Configurations
Jack E. Baldwin; Artem Melman; Victor Lee; Catherine R. Firkin; Roger C. Whitehead; Journal of the American Chemical Society 120 (1998) 8559–8560; doi:10.1021/ja980765v

data_4116817
_publ_section_title
;
 Biomimetic Synthesis of (-)-Xestospongin A, (+)-Xestospongin C,
 (+)-Araguspongine B and the Correction of Their Absolute Configurations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8559
_journal_page_last               8560
_journal_paper_doi               10.1021/ja980765v
_journal_volume                  120
_journal_year                    1998
_chemical_compound_source
;

?

;
_chemical_formula_moiety         ' C28 H46 O2 N2 '
_chemical_formula_sum            'C28 H46 N2 O2'
_chemical_formula_weight         442.69
_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     direct
_audit_creation_date             98-01-14
_audit_creation_method           CRYSTALS
_cell_angle_alpha                90
_cell_angle_beta                 96.33(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.62(1)
_cell_length_b                   9.88(1)
_cell_length_c                   15.31(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      43
_cell_measurement_theta_min      19
_cell_volume                     1296(2)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction
;

RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994)

;
_computing_molecular_graphics
;

 CAMERON (Watkin, Prout & Pearce,  1996)

;
_computing_publication_material
;

CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)

;
_computing_structure_refinement
;

CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)

;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       '  Enraf-nonius CAD4 '
_diffrn_measurement_method       2\q/\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2907
_diffrn_reflns_theta_max         74.17
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        1.58
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.51
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '\y scan,(North et al, 1968)'
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.14
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             489.18
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details ' from Flack enantiopole 0.000'
_refine_ls_extinction_coef       57.5(55)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_obs   1.0308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2714
_refine_ls_R_factor_obs          0.0311
_refine_ls_shift/esd_max         0.000165
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Chebychev polynomial (Carruthers & Watkin, 1979)
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0393
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_observed          2714
_reflns_number_total             2798
_reflns_observed_criterion       >3.00\s(I)
_cod_data_source_file            ja980765v.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct_Methods' was changed to
'direct'.

'_atom_sites_solution_hydrogens' value 'Geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1294.71
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C28 H46 O2 N2 '
_cod_database_code               4116817