A Simple and Modular Strategy for Small Molecule Synthesis: Iterative Suzuki-Miyaura Coupling of B-Protected Haloboronic Acid Building Blocks
Eric P. Gillis; Martin D. Burke; Journal of the American Chemical Society 129 (2007) 6716–6717; doi:10.1021/ja0716204

data_4109461
_publ_section_title
;
 A Simple and Modular Strategy for Small Molecule Synthesis: Iterative
 Suzuki-Miyaura Coupling of B-Protected Haloboronic Acid Building Blocks
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6716
_journal_page_last               6717
_journal_paper_doi               10.1021/ja0716204
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         '4(C13 H13 B Br N O4), C4 H8 O'
_chemical_formula_sum            'C56 H60 B4 Br4 N4 O17'
_chemical_formula_weight         1423.96
_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
; 
2007-01-22   text and data added, srw 
;
_cell_angle_alpha                105.600(5)
_cell_angle_beta                 100.232(5)
_cell_angle_gamma                91.152(5)
_cell_formula_units_Z            2
_cell_length_a                   10.823(3)
_cell_length_b                   13.265(4)
_cell_length_c                   23.208(6)
_cell_measurement_reflns_used    824
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      17.62
_cell_measurement_theta_min      2.40
_cell_volume                     3150.0(15)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  g02nas
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_sigmaI/netI    0.1400
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32853
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        13.9
_diffrn_standards_interval_time  205
_diffrn_standards_number         34
_exptl_absorpt_coefficient_mu    2.625
_exptl_absorpt_correction_T_max  0.8530
_exptl_absorpt_correction_T_min  0.3134
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1440
_exptl_crystal_id                g02nas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -1 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     928
_refine_ls_number_reflns         11493
_refine_ls_number_restraints     1682
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.2010
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0912P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1932
_reflns_number_gt                4040
_reflns_number_total             11493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0716204si20070411_114807.cif
_cod_data_source_block           g02nas
_cod_original_cell_volume        3149.8(15)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4109461