Straightforward assembly of the octahydroisoquinoline core of morphinan alkaloids.
Dunet, Julie; Lebeuf, Raphaël; Bose, Gopal; Robert, Frédéric; Landais, Yannick; Organic letters 12 (2010) 2178–2181; doi:10.1021/ol1004627

data_1502932
_publ_section_title
;
 Straightforward assembly of the octahydroisoquinoline core of morphinan
 alkaloids.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2178
_journal_page_last               2181
_journal_paper_doi               10.1021/ol1004627
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.89
_cell_angle_beta                 80.85
_cell_angle_gamma                72.13
_cell_formula_units_Z            4
_cell_length_a                   10.652
_cell_length_b                   12.569
_cell_length_c                   15.424
_cell_measurement_temperature    213(2)
_cell_volume                     1853.163
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25717
_diffrn_reflns_theta_full        72.48
_diffrn_reflns_theta_max         72.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         6737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0735
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.025
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2611
_reflns_number_gt                6260
_reflns_number_total             6737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1004627_si_005.cif
_cod_data_source_block           jd598
_cod_original_cell_volume        1853.2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502932