Synthesis of rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol. An unusual double rearrangement leading to the ortho- and para-f oxide-bridged phenylmorphan isomers.
Kodato, Shinichi; Linders, Joannes T. M.; Gu, Xiao-Hui; Yamada, Koichiro; Flippen-Anderson, Judith L; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Organic & biomolecular chemistry 2 (2004) 330–336; doi:10.1039/b312633c

data_7151597
_publ_section_title
;
 Synthesis of
 rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol.
 An unusual double rearrangement leading to the ortho- and para-f
 oxide-bridged phenylmorphan isomers.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              330
_journal_page_last               336
_journal_paper_doi               10.1039/b312633c
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C17 H25 Cl N O2, H2 O, Cl'
_chemical_formula_sum            'C17 H27 Cl2 N O3'
_chemical_formula_weight         364.30
_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                 92.720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5210(10)
_cell_length_b                   8.1870(10)
_cell_length_c                   17.336(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     924.5(2)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_refinement  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1989
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker XPREP v5.1 (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0551P)^2^+0.1304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                1674
_reflns_number_total             1767
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b312633c.txt
_cod_data_source_block           rice45
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151597