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_4027404
_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         'C19 H31 Cl1 N2 O1'
_chemical_formula_sum            'C19 H31 Cl N2 O'
_chemical_formula_weight         338.92
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                102.695(3)
_cell_angle_beta                 94.987(3)
_cell_angle_gamma                109.832(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2921(4)
_cell_length_b                   7.3234(4)
_cell_length_c                   9.7967(6)
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     472.62(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3477
_diffrn_reflns_theta_full        25.238
_diffrn_reflns_theta_max         27.433
_diffrn_reflns_theta_min         5.294
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.0002507
_refine_ls_shift/su_mean         0.0000162
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.08P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0740
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0740
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              8
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                3373
_reflns_number_total             3477
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.18
_oxford_refine_ls_r_factor_ref   0.0319
_oxford_refine_ls_scale          2.335(15)
_oxford_reflns_number_all        3477
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo3012732_si_002_1.cif
_cod_data_source_block           58.HCl
_cod_original_formula_sum        'C19 H31 Cl1 N2 O1'
_cod_database_code               4027404