Simple, Efficient, and Modular Syntheses of Polyene Natural Products via Iterative Cross-Coupling
Suk Joong Lee; Kaitlyn C. Gray; James S. Paek; Martin D. Burke; Journal of the American Chemical Society 130 (2008) 466–468; doi:10.1021/ja078129x

data_4107303
_publ_section_title
;
 Simple, Efficient, and Modular Syntheses of Polyene Natural Products via
 Iterative Cross-Coupling
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              466
_journal_page_last               468
_journal_paper_doi               10.1021/ja078129x
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C13 H21 B2 N O6, 0.125(C4 H8 O2)'
_chemical_formula_sum            'C13.5 H22 B2 N O6.25'
_chemical_formula_weight         319.94
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2006-06-01   text and data added, srw 
;
_cell_angle_alpha                87.714(12)
_cell_angle_beta                 84.740(11)
_cell_angle_gamma                80.831(12)
_cell_formula_units_Z            4
_cell_length_a                   6.9032(14)
_cell_length_b                   16.060(3)
_cell_length_c                   16.510(3)
_cell_measurement_reflns_used    688
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      13.95
_cell_measurement_theta_min      2.48
_cell_volume                     1798.8(6)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'APEX2 V1.0-27 (Bruker, 2004)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  ga74kas
_diffrn_reflns_av_R_equivalents  0.1797
_diffrn_reflns_av_sigmaI/netI    0.2261
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15213
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       acicular
_exptl_crystal_F_000             680
_exptl_crystal_id                ga74kas
_exptl_crystal_preparation
; 
The data crystal was mounted using epoxy to a 0.3 mm cryo-loop 
(Hampton Research) with the (0 1 0) scattering planes roughly normal 
to the spindle axis. 
;
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.345
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     506
_refine_ls_restrained_S_all      1.322
_refine_ls_R_factor_all          0.2781
_refine_ls_R_factor_gt           0.1097
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2804
_reflns_number_gt                1285
_reflns_number_total             3734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja078129x-file006.cif
_cod_data_source_block           ga74kas
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C13.50 H22 B2 N O6.25'
_cod_database_code               4107303