Biogenetically inspired total syntheses of lycopodium alkaloids, (+)-flabellidine and (-)-lycodine.
Azuma, Masayuki; Yoshikawa, Tetsuya; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu; Journal of the American Chemical Society 136 (2014) 11618–11621; doi:10.1021/ja507016g

data_4122384
_publ_section_title
;
 Biogenetically inspired total syntheses of lycopodium alkaloids,
 (+)-flabellidine and (-)-lycodine.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11618
_journal_page_last               11621
_journal_paper_doi               10.1021/ja507016g
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C30 H32 Br2 N2 O2'
_chemical_formula_weight         612.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3618(15)
_cell_length_b                   11.6411(10)
_cell_length_c                   25.598(2)
_cell_measurement_temperature    173.(2)
_cell_volume                     5471.6(8)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17032
_diffrn_reflns_theta_full        21.16
_diffrn_reflns_theta_max         21.16
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    2.993
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_process_details
;
;
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.319
_refine_ls_abs_structure_details
;
Flack x determined using 1974 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.471(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+16.6955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                4942
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja507016g_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4122382--4122384.cif.'
_cod_database_code               4122384
_shelx_res_checksum              48101
_shelx_hkl_checksum              3598