Combining two-directional synthesis and tandem reactions: an efficient strategy for the total syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.
Rejzek, Martin; Stockman, Robert A.; Hughes, David L.; Organic & biomolecular chemistry 3 (2005) 73–83; doi:10.1039/b413052a

data_7150011
_publ_section_title
;
 Combining two-directional synthesis and tandem reactions: an efficient
 strategy for the total syntheses of (+/-)-hippodamine and
 (+/-)-epi-hippodamine.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              73
_journal_page_last               83
_journal_paper_doi               10.1039/b413052a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C13 H23 N O'
_chemical_formula_structural     'a hippodamine derivative'
_chemical_formula_sum            'C13 H23 N O'
_chemical_formula_weight         209.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.660(2)
_cell_length_b                   14.610(3)
_cell_length_c                   10.367(2)
_cell_measurement_temperature    140(1)
_cell_volume                     1160.0(4)
_computing_cell_refinement       'DENZO/CELL (Otwinowski and Minor, 1985)'
_computing_data_collection       'MSC R-Axis-II control software'
_computing_data_reduction        'DENZO, SCALEPACK (Otwinowski and Minor, 1985)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device       'Rigaku R-Axis-IIc'
_diffrn_measurement_method       'image-plate oscillation photos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6714
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            'clear, colourless,'
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'tapered rectangular prism'
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0384P)^2^+0.3841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1851
_reflns_number_total             2043
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b413052a.txt
_cod_data_source_block           martinr1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7150011