Asymmetric Syntheses of the Homalium Alkaloids (-)-(S,S)-Homaline and (-)-(R,R)-Hopromine
Stephen G. Davies; James A. Lee; Paul M. Roberts; Jeffrey P. Stonehouse; James E. Thomson; Journal of Organic Chemistry 77 (2012) 7028–7045; doi:10.1021/jo3012732

data_4027405
_publ_contact_author             'Stephen G. Davies'
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 Asymmetric Syntheses of the Homalium Alkaloids (-)-(S,S)-Homaline and
 (-)-(R,R)-Hopromine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7028
_journal_page_last               7045
_journal_paper_doi               10.1021/jo3012732
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 N2 O1'
_chemical_formula_sum            'C13 H18 N2 O'
_chemical_formula_weight         218.30
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_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.696(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0474(2)
_cell_length_b                   6.8974(2)
_cell_length_c                   13.9812(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     579.20(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_theta_max         76.785
_diffrn_reflns_theta_min         3.183
_diffrn_standards_number         0
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_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.9328
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_exptl_crystal_description       plate
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_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
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_refine_ls_extinction_method     none
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_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.0002340
_refine_ls_shift/su_mean         0.0000313
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.09P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
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_oxford_diffrn_Wilson_scale      0.00
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_oxford_refine_ls_scale          13.4(4)
_oxford_reflns_number_all        6077
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo3012732_si_002_2.cif
_cod_data_source_block           39
_cod_original_cell_volume        579.19(3)
_cod_original_formula_sum        'C13 H18 N2 O1'
_cod_database_code               4027405