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_1507156
_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         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_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   difmap
_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                   6.2522(5)
_cell_length_b                   7.9375(6)
_cell_length_c                   18.4228(16)
_cell_measurement_reflns_used    5336
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     914.27(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10354
_diffrn_reflns_theta_full        29.132
_diffrn_reflns_theta_max         29.727
_diffrn_reflns_theta_min         2.211
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9096
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.0004050
_refine_ls_shift/su_mean         0.0000415
_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: 
 20.8 34.0 18.8 6.66 1.19 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1316
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1314
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2405
_reflns_number_total             2579
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.30
_oxford_diffrn_Wilson_scale      10.12
_oxford_refine_ls_r_factor_ref   0.0550
_oxford_reflns_number_all        2576
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol300133x_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'refu' changed to
'refU' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1507156
_iucr_refine_instruction_details_constraints
;
FULL  C(2,X'S,U'S) UNTIL O(10) H(21,U[ISO]) UNTIL LAST 
EQUIV H(21,U[ISO]) UNTIL LAST 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
END                                                                             
;