Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolides.
Su, Qibin; Beeler, Aaron B.; Lobkovsky, Emil; Porco, Jr, John A; Panek, James S.; Organic letters 5 (2003) 2149–2152; doi:10.1021/ol034608z

data_1507320
_publ_section_title
;
 Stereochemical diversity through cyclodimerization: synthesis of
 polyketide-like macrodiolides.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2149
_journal_page_last               2152
_journal_paper_doi               10.1021/ol034608z
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C18 H28 O8'
_chemical_formula_weight         372.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           3
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2y'
_symmetry_space_group_name_H-M   'P 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4095(8)
_cell_length_b                   5.3468(4)
_cell_length_c                   15.4399(11)
_cell_measurement_temperature    173(2)
_cell_volume                     932.30(12)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       '0.3 deg omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9211
_diffrn_reflns_theta_full        32.46
_diffrn_reflns_theta_max         32.46
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.831397
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          4.372
_refine_ls_shift/su_mean         0.239
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.0625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                4832
_reflns_number_total             5673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034608zsi20030408_064812.cif
_cod_data_source_block           porco12
_cod_original_sg_symbol_H-M      P2
_cod_database_code               1507320