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_7151224
_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 rmad
_chemical_formula_moiety         'C22 H31 N O5 S, C H2 Cl2'
_chemical_formula_sum            'C23 H33 Cl2 N O5 S'
_chemical_formula_weight         506.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   9.7734(11)
_cell_length_b                   13.3223(16)
_cell_length_c                   20.380(2)
_cell_measurement_reflns_used    5763
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.31
_cell_volume                     2653.6(5)
_computing_cell_refinement       'Apex2 (Bruker-Nonius, 2004)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2004)'
_computing_data_reduction
;
SAINT enbedded in Apex2 (Bruker-Nonius, 2004)
;
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean
;
120 microns
;
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_detector       'Apex camera'
_diffrn_radiation_monochromator
;
graphite model mounted in "parallel" mode
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            100306
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
Flack H D (1983), Acta Cryst. A39, 876-881
2257 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+1.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                4212
_reflns_number_total             5205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b603857c.txt
_cod_data_source_block           es443
_cod_original_cell_volume        2653.5(5)
_cod_database_code               7151224