Stereoselective Stille Coupling of Enantiopure Haloallenes and Alkenylstannanes for the Synthesis of Allenyl Carotenoids. Experimental and Computational Studies
Belén Vázquez; Raquel Pereira; Martιn Pérez; Rosana Álvarez; Angel R. de Lera; Journal of Organic Chemistry 73 (2008) 6534–6541; doi:10.1021/jo800756b

data_4023626
_publ_section_title
;
 Stereoselective Stille Coupling of Enantiopure Haloallenes and
 Alkenylstannanes for the Synthesis of Allenyl Carotenoids.
 Experimental and Computational Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6534
_journal_page_last               6541
_journal_paper_doi               10.1021/jo800756b
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C24 H29 N O5 S2'
_chemical_formula_weight         475.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.447(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2154(8)
_cell_length_b                   21.8191(17)
_cell_length_c                   11.5734(9)
_cell_measurement_temperature    173(2)
_cell_volume                     2474.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15659
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.874679
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          .49
_exptl_crystal_size_mid          .33
_exptl_crystal_size_min          .24
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         9768
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          1.064
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                7003
_reflns_number_total             9768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800756b_si_001.cif
_cod_data_source_block           ar1972s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023626