Position of coordination of the lithium ion determines the regioselectivity of demethylations of 3,4-dimethoxymorphinans with L-selectride.
Wu, Huifang; Thatcher, Linn N.; Bernard, Denzil; Parrish, Damon A.; Deschamps, Jeffrey R.; Rice, Kenner C.; MacKerell, Jr, Alexander D; Coop, Andrew; Organic letters 7 (2005) 2531–2534; doi:10.1021/ol050433c

data_1506557
_publ_section_title
;
 Position of coordination of the lithium ion determines the
 regioselectivity of demethylations of 3,4-dimethoxymorphinans with
 L-selectride.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2531
_journal_page_last               2534
_journal_paper_doi               10.1021/ol050433c
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H33 N O5'
_chemical_formula_sum            'C24 H33 N O5'
_chemical_formula_weight         415.51
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.416(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9632(14)
_cell_length_b                   9.5308(17)
_cell_length_c                   15.805(3)
_cell_measurement_reflns_used    686
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      3.17
_cell_volume                     1048.6(3)
_computing_cell_refinement       'Bruker SMART v5.059 (Bruker, 1999)'
_computing_data_collection       'Bruker SMART v5.059 (Bruker, 1999)'
_computing_data_reduction
;
Bruker SAINT v6.02A (Bruker, 2000a), Bruker XPREP v5.1 (Bruker, 1997)
;
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000b)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.776
_diffrn_measured_fraction_theta_max 0.776
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5991
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  variable
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.01 (Bruker, 2000c)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.3106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                3070
_reflns_number_total             3597
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol050433csi20050517_050156.cif
_cod_data_source_block           coop11
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1506557