Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling.
Besong, Gilbert; Jarowicki, Krzysztof; Kocienski, Philip J.; Sliwinski, Eric; Boyle, F. Thomas; Organic & biomolecular chemistry 4 (2006) 2193–2207; doi:10.1039/b603857c

data_7151225
_publ_section_title
;
 Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl
 oxidative coupling.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2193
_journal_page_last               2207
_journal_paper_doi               10.1039/b603857c
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H42 B N O7, H2 O'
_chemical_formula_sum            'C25 H44 B N O8'
_chemical_formula_weight         497.42
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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            8
_cell_length_a                   13.3627(3)
_cell_length_b                   15.6068(3)
_cell_length_c                   27.3395(7)
_cell_measurement_reflns_used    73652
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     5701.6(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
;
DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
ORTEP-III Version 1.08 (Farrugia, 2005)
;
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR92
Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.;
Giacovazzo, C.; Guagliardi, A.; Polidori, G.
J. Appl. Cryst. 1994, 27, 435-436.
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method
;
phi and omega scans to fill the asymmetric unit
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29479
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0519P)^2^+0.4241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                4514
_reflns_number_total             5715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b603857c.txt
_cod_data_source_block           kj18
_cod_database_code               7151225