The Stille reaction in the synthesis of carotenoid butenolides: synthesis of 6'-epi-peridinin.
Vaz, Belén; Alvarez, Rosana; Brückner, Reinhard; de Lera, Angel R.; Organic letters 7 (2005) 545–548; doi:10.1021/ol0478281

data_1506492
_publ_section_title
;
 The Stille reaction in the synthesis of carotenoid butenolides: synthesis
 of 6'-epi-peridinin.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              545
_journal_page_last               548
_journal_paper_doi               10.1021/ol0478281
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C13 H19 Br O3'
_chemical_formula_weight         303.19
_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
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_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                   7.9727(8)
_cell_length_b                   12.9910(13)
_cell_length_c                   15.0747(15)
_cell_measurement_temperature    293(2)
_cell_volume                     1561.3(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      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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
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_diffrn_reflns_av_sigmaI/netI    0.0936
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8573
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.07
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_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.443409
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(14)
_refine_ls_extinction_coef       0.0008(9)
_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   0.783
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.783
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                1372
_reflns_number_total             3393
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0478281si20041026_022834.cif
_cod_data_source_block           ar2097cs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      P2(1)2(1)2(1)
_cod_database_code               1506492