Efficient total synthesis of (+)-dihydropinidine, (-)-epidihydropinidine, and (-)-pinidinone.
Kavala, Miroslav; Mathia, František; Kožíšek, Jozef; Szolcsányi, Peter; Journal of natural products 74 (2011) 803–808; doi:10.1021/np100852p

data_1501805
_publ_section_title
;
 Efficient total synthesis of (+)-dihydropinidine, (-)-epidihydropinidine,
 and (-)-pinidinone.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              803
_journal_page_last               808
_journal_paper_doi               10.1021/np100852p
_journal_volume                  74
_journal_year                    2011
_chemical_formula_sum            'C9 H20 Cl N'
_chemical_formula_weight         177.71
_space_group_IT_number           21
_symmetry_space_group_name_Hall  'C 2 2'
_symmetry_space_group_name_H-M   'C 2 2 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   9.90868(12)
_cell_length_b                   34.4359(6)
_cell_length_c                   14.35610(16)
_cell_measurement_temperature    293(2)
_cell_volume                     4898.51(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42033
_diffrn_reflns_theta_full        75.04
_diffrn_reflns_theta_max         75.03
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    2.363
_exptl_crystal_density_diffrn    0.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1748P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2177
_reflns_number_gt                4415
_reflns_number_total             4914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np100852p_si_003.cif
_cod_data_source_block           f:\data_f~1\szolcs~1\exp_707\stoe\exp_707
_cod_original_cell_volume        4898.51(11)
_cod_database_code               1501805