Synthesis of (±)-acetylnorloline via stereoselective tethered aminohydroxylation.
Hovey, M. Todd; Eklund, Emily J.; Pike, Robert D.; Mainkar, Anshul A.; Scheerer, Jonathan R.; Organic letters 13 (2011) 1246–1249; doi:10.1021/ol200155p

data_1502050
_publ_section_title
;
 Synthesis of (+-)-acetylnorloline via stereoselective tethered
 aminohydroxylation.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1246
_journal_page_last               1249
_journal_paper_doi               10.1021/ol200155p
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C23 H32 N2 O12 S2'
_chemical_formula_sum            'C23 H32 N2 O12 S2'
_chemical_formula_weight         592.63
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.5800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3138(6)
_cell_length_b                   9.4146(3)
_cell_length_c                   13.7762(4)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      4.18
_cell_volume                     2740.19(14)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'XSHELL (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w and \y'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29210
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_T_max  0.8821
_exptl_absorpt_correction_T_min  0.4831
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0447P)^2^+3.0954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                4338
_reflns_number_total             4855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200155p_si_002.cif
_cod_data_source_block           p21onc
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502050