Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues of (+)-discodermolide.
Smith, 3rd, Amos B; Xian, Ming; Liu, Fenghua; Organic letters 7 (2005) 4613–4616; doi:10.1021/ol051691c

data_1506705
_publ_section_title
;
 Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues
 of (+)-discodermolide.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4613
_journal_page_last               4616
_journal_paper_doi               10.1021/ol051691c
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C21 H33 I O6'
_chemical_formula_weight         508.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7031(17)
_cell_length_b                   7.6834(11)
_cell_length_c                   14.286(2)
_cell_measurement_temperature    143(1)
_cell_volume                     1166.3(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6661
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7770
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.027(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                3619
_reflns_number_total             3800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051691csi20050718_021423.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21     '
_cod_database_code               1506705