Gold-Catalyzed Intramolecular Allylic Amination of 2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (\±)-Angustureine
Prasath Kothandaraman; Shi Jia Foo; Philip Wai Hong Chan; Journal of Organic Chemistry 74 (2009) 5947–5952; doi:10.1021/jo900917q

data_4024759
_publ_section_title
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Gold-Catalyzed Intramolecular Allylic Amination of
2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (\+-)-Angustureine
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5947
_journal_page_last               5952
_journal_paper_doi               10.1021/jo900917q
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H21 N O2 S'
_chemical_formula_sum            'C23 H21 N O2 S'
_chemical_formula_weight         375.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.572(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1459(5)
_cell_length_b                   8.8607(4)
_cell_length_c                   19.6255(8)
_cell_measurement_reflns_used    4924
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.53
_cell_volume                     1916.57(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21704
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.076
_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     246
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1212P)^2^+0.7098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.2094
_reflns_number_gt                2395
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900917q_si_004.cif
_cod_data_source_block           chan47
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024759