Asymmetric synthesis of the oxygenated polycyclic system of (+)-harringtonolide.
Abdelkafi, Hajer; Herson, Patrick; Nay, Bastien; Organic letters 14 (2012) 1270–1273; doi:10.1021/ol300133x

data_1507155
_publ_section_title
;
 Asymmetric synthesis of the oxygenated polycyclic system of
 (+)-harringtonolide.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1270
_journal_page_last               1273
_journal_paper_doi               10.1021/ol300133x
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.28
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2405(5)
_cell_length_b                   8.5569(7)
_cell_length_c                   27.083(2)
_cell_measurement_reflns_used    360
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     1214.47(18)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            11511
_diffrn_reflns_theta_full        34.301
_diffrn_reflns_theta_max         35.001
_diffrn_reflns_theta_min         3.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bloc
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0788
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.0008056
_refine_ls_shift/su_mean         0.0000654
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 5.37 7.29 2.46 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1089
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1089
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              43
_reflns_limit_l_min              0
_reflns_number_gt                2784
_reflns_number_total             3006
_reflns_threshold_expression     I>2.0\s(I)
_oxford_refine_ls_r_factor_ref   0.0428
_oxford_refine_ls_scale          0.887(3)
_oxford_reflns_number_all        3002
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol300133x_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1507155
_iucr_refine_instruction_details_constraints
;
FULL C(1,X'S,U'S) UNTIL O(4) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
END                                                                             
;