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_1502049
_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_absolute_configuration unk
_chemical_formula_moiety         'C8 H10 N2 O3'
_chemical_formula_sum            'C8 H10 N2 O3'
_chemical_formula_weight         182.18
_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                   5.18270(10)
_cell_length_b                   8.0456(2)
_cell_length_c                   20.4481(5)
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.73
_cell_measurement_theta_min      4.32
_cell_volume                     852.64(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9183
_diffrn_reflns_theta_full        66.89
_diffrn_reflns_theta_max         66.89
_diffrn_reflns_theta_min         4.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.7129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0438P)^2^+0.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                1349
_reflns_number_total             1505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200155p_si_001.cif
_cod_data_source_block           p212121
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502049