Synthesis-Guided Structure Revision of the Sarcodonin, Sarcoviolin, and Hydnellin Natural Product Family
David W. Lin; Takeshi Masuda; Moritz B. Biskup; Jonathan D. Nelson; Phil S. Baran; Journal of Organic Chemistry 76 (2011) 1013–1030; doi:10.1021/jo102228j

data_4026057
_publ_section_title
;
 Synthesis-Guided Structure Revision of the Sarcodonin, Sarcoviolin, and
 Hydnellin Natural Product Family
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1013
_journal_page_last               1030
_journal_paper_doi               10.1021/jo102228j
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C24 H26 N O7'
_chemical_formula_weight         440.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.983(2)
_cell_length_b                   10.796(2)
_cell_length_c                   20.198(4)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.6
_cell_measurement_theta_min      4.0
_cell_volume                     2176.9(7)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Parallelepiped
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      'not applicable'
_exptl_crystal_description       Colorless
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0827
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1874
_reflns_number_gt                2943
_reflns_number_total             3830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102228j_si_006.cif
_cod_data_source_block           dlin
_cod_original_cell_volume        2176.9(8)
_cod_database_code               4026057