Short, asymmetric synthesis of epi-morphine ACNO analogues.
Heureux, Nicolas; Wouters, Johan; Norberg, Bernadette; Markó, István E; Organic & biomolecular chemistry 4 (2006) 3898–3900; doi:10.1039/b610148h

data_7151316
_publ_section_title
;
 Short, asymmetric synthesis of epi-morphine ACNO analogues.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3898
_journal_page_last               3900
_journal_paper_doi               10.1039/b610148h
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H24 N2 O4'
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 90.461(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.576(3)
_cell_length_b                   15.667(2)
_cell_length_c                   7.4650(10)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.9
_cell_measurement_theta_min      17.7
_cell_volume                     2055.5(5)
_computing_cell_refinement       NoniusCAD4/MACH3(2000)
_computing_data_collection       NoniusCAD4/MACH3(2000)
_computing_data_reduction        'Platon2001 (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  nonius
_diffrn_measurement_method       \q/q2\q
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2287
_diffrn_reflns_theta_full        74.94
_diffrn_reflns_theta_max         74.94
_diffrn_reflns_theta_min         3.78
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.8988
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0787P)^2^+0.2740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                2235
_reflns_number_total             2287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610148h.txt
_cod_data_source_block           uclnh4
_cod_original_sg_symbol_Hall     C-2yc
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7151316