Stereoretentive Suzuki-Miyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to (-)-Peridinin
Eric M. Woerly; Alan H. Cherney; Erin K. Davis; Martin D. Burke; Journal of the American Chemical Society 132 (2010) 6941–6943; doi:10.1021/ja102721p

data_4102462
_publ_contact_author
; 
Gray, Danielle L. 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       dgray@illinois.edu
_publ_contact_author_fax         '1  217 244 8068'
_publ_contact_author_phone       '1  217 244 1708'
_publ_section_title
;
 Stereoretentive Suzuki-Miyaura Coupling of Haloallenes Enables Fully
 Stereocontrolled Access to (-)-Peridinin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6941
_journal_page_last               6943
_journal_paper_doi               10.1021/ja102721p
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         '4(C13 H13 B Br N O6), C3 H6 O'
_chemical_formula_sum            'C55 H58 B4 Br4 N4 O25'
_chemical_formula_weight         1537.93
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.247(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3530(6)
_cell_length_b                   17.5538(13)
_cell_length_c                   24.6460(18)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      19.39
_cell_measurement_theta_min      2.74
_cell_volume                     3178.7(4)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \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_radiation_wavelength_id  ba02eas
_diffrn_reflns_av_R_equivalents  0.1513
_diffrn_reflns_av_sigmaI/netI    0.1280
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37930
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_T_max  0.9338
_exptl_absorpt_correction_T_min  0.6025
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             1552
_exptl_crystal_id                ba02eas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (2 -2 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5835
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0405P)^2^+1.6787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                2588
_reflns_number_total             5835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102721p_si_003.cif
_cod_data_source_block           ba02eas
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4102462