Synthesis of Chiral Building Blocks for Oxygenated Terpenoids through a Simultaneous and Stereocontrolled Construction of Contiguous Quaternary Stereocenters by an Ireland-Claisen Rearrangement.
Akahori, Yoshihiro; Yamakoshi, Hiroyuki; Sawayama, Yuki; Hashimoto, Shunichi; Nakamura, Seiichi; The Journal of organic chemistry 79 (2014) 720–735; doi:10.1021/jo402537u

data_4028977
_publ_section_title
;
 Synthesis of Chiral Building Blocks for Oxygenated Terpenoids through a
 Simultaneous and Stereocontrolled Construction of Contiguous Quaternary
 Stereocenters by an Ireland-Claisen Rearrangement.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              720
_journal_page_last               735
_journal_paper_doi               10.1021/jo402537u
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H39 I O4 Si'
_chemical_formula_sum            'C30 H39 I O4 Si'
_chemical_formula_weight         618.60
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0598(5)
_cell_length_b                   10.3875(5)
_cell_length_c                   27.6339(14)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.45
_cell_volume                     2887.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            30513
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.183
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'without a literature citation'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_coef       0
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+2.0703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                5986
_reflns_number_total             6180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402537u_si_002.cif
_cod_data_source_block           lactone6_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4028977