Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran E and Other Targets of Interest.
Blaisdell, Thomas P.; Morken, James P.; Journal of the American Chemical Society 137 (2015) 8712–8715; doi:10.1021/jacs.5b05477

data_4124339
_publ_section_title
;
 Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of
 Debromohamigeran E and Other Targets of Interest.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8712
_journal_page_last               8715
_journal_paper_doi               10.1021/jacs.5b05477
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C20 H38 B2 O5, C6 H14 O2'
_chemical_formula_sum            'C26 H52 B2 O7'
_chemical_formula_weight         498.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.059(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8734(6)
_cell_length_b                   12.5634(7)
_cell_length_c                   21.8982(12)
_cell_measurement_reflns_used    8121
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.58
_cell_volume                     2974.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         1.870
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.9509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4664
_reflns_number_total             7385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05477_si_002.cif
_cod_data_source_block           C20H38B2O5(C6H14O2)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               4124339
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
_shelx_res_checksum              40676
_shelx_hkl_checksum              77399