Total synthesis and stereochemical assignment of (±)-sorbiterrin a.
Qi, Chao; Qin, Tian; Suzuki, Daisuke; Porco, Jr, John A; Journal of the American Chemical Society 136 (2014) 3374–3377; doi:10.1021/ja500854q

data_4121487
_publ_section_title
;
 Total synthesis and stereochemical assignment of (+-)-sorbiterrin a.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3374
_journal_page_last               3377
_journal_paper_doi               10.1021/ja500854q
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C20 H19 I O6'
_chemical_formula_sum            'C20 H19 I O6'
_chemical_formula_weight         482.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_audit_update_record
;
2013-12-05 # Formatted by publCIF
;
_cell_angle_alpha                89.959(2)
_cell_angle_beta                 68.696(2)
_cell_angle_gamma                68.458(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8558(6)
_cell_length_b                   10.4095(7)
_cell_length_c                   11.3264(7)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.643
_cell_measurement_theta_min      5.214
_cell_volume                     894.15(10)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30029
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.679
_diffrn_reflns_theta_min         4.239
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.390
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5510
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.238
_refine_diff_density_max         1.836
_refine_diff_density_min         -1.815
_refine_diff_density_rms         0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     416
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+1.7025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             3152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500854q_si_003.cif
_cod_data_source_block           chao6_0m
_cod_database_code               4121487
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
4.a Ternary CH refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C32(H32)
4.b Aromatic/amide H refined with riding coordinates:
 C38(H38)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C)
4.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O10(H10)
;
_shelx_res_checksum              71622
_shelx_hkl_checksum              20529