Synthesis of (±)-Aphanorphine Using Rh-Catalyzed Cyclohydrocarbonylation.
Chiou, Wen-Hua; Chen, Po-Chou; The Journal of organic chemistry 82 (2017) 8213–8219; doi:10.1021/acs.joc.7b00923

data_4032744
_publ_section_title
;
 Synthesis of (+-)-Aphanorphine Using Rh-Catalyzed
 Cyclohydrocarbonylation.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8213
_journal_page_last               8219
_journal_paper_doi               10.1021/acs.joc.7b00923
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                99.406(3)
_cell_angle_beta                 90.418(3)
_cell_angle_gamma                93.521(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6887(5)
_cell_length_b                   9.6050(7)
_cell_length_c                   10.7854(8)
_cell_measurement_reflns_used    7071
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.11
_cell_volume                     682.20(9)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7071
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9630
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.032(8)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0887P)^2^+0.2552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                2157
_reflns_number_total             2755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00923_si_003.cif
_cod_data_source_block           27b
_cod_database_code               4032744