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_7150010
_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     'tricyclic C13 H23 N O'
_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 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                 102.381(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.766(3)
_cell_length_b                   9.337(2)
_cell_length_c                   13.7672(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     1226.2(5)
_computing_cell_refinement       'CAD4/EXPRESS (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD4/EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'CAD4 (Hursthouse, 1976)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'scintillation counter; \w/\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2146
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        5.7
_diffrn_standards_interval_time  '10000 s'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.401
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'EMPABS, (Sheldrick et al, 1977)'
_exptl_crystal_colour            'clear, colourless'
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                1263
_reflns_number_total             2146
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b413052a.txt
_cod_data_source_block           martinr3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'psi-scans' was replaced
with 'psi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1226.1(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150010