Total syntheses of (+)-echinopine A and B: determination of absolute stereochemistry.
Magauer, Thomas; Mulzer, Johann; Tiefenbacher, Konrad; Organic letters 11 (2009) 5306–5309; doi:10.1021/ol902263k

data_1504279
_publ_section_title
;
 Total syntheses of (+)-echinopine A and B: determination of absolute
 stereochemistry.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5306
_journal_page_last               5309
_journal_paper_doi               10.1021/ol902263k
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   7.680(3)
_cell_length_b                   7.680(3)
_cell_length_c                   37.274(19)
_cell_measurement_reflns_used    611
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      19.54
_cell_measurement_theta_min      4.85
_cell_volume                     1904.0(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11625
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9996
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0616P)^2^+1.5684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                1767
_reflns_number_total             2370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902263k_si_001.cif
_cod_data_source_block           thma261
_cod_original_sg_symbol_H-M      P3221
_cod_database_code               1504279