Total Synthesis of (+)-Ambruticin S: Probing the Pharmacophoric Subunit
Stephen Hanessian; Thilo Focken; Xueling Mi; Rupal Oza; Bin Chen; Dougal Ritson; Renaud Beaudegnies; Journal of Organic Chemistry 75 (2010) 5601–5618; doi:10.1021/jo100956v

data_4025597
_publ_section_title
;
 Total Synthesis of (+)-Ambruticin S: Probing the Pharmacophoric Subunit
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5601
_journal_page_last               5618
_journal_paper_doi               10.1021/jo100956v
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C31 H44 O8'
_chemical_formula_sum            'C31 H44 O8'
_chemical_formula_weight         544.66
_chemical_melting_point          366.6(5)
_chemical_name_common            'Ambruticin triformate'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 110.908(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.5260(9)
_cell_length_b                   5.2293(3)
_cell_length_c                   20.0132(12)
_cell_measurement_reflns_used    20187
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.96
_cell_measurement_theta_min      2.36
_cell_volume                     1517.88(16)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34060
_diffrn_reflns_theta_full        69.26
_diffrn_reflns_theta_max         69.26
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.9727
_exptl_absorpt_correction_T_min  0.3673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), 1829 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0814P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                3720
_reflns_number_total             5002
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100956v_si_002.cif
_cod_data_source_block           bent53
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '93-94 Celsius' was changed to
'366.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (78
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (59 times).

'_geom_torsion_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(103 times).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1517.88(15)
_cod_database_code               4025597