Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine.
Alujas-Burgos, Sílvia; Oliveras-González, Cristina; Álvarez-Larena, Ángel; Bayón, Pau; Figueredo, Marta; The Journal of organic chemistry 83 (2018) 5052–5057; doi:10.1021/acs.joc.8b00390

data_4035517
_publ_section_title
;
 Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis
 of (-)-9a epi-Hippocasine.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5052
_journal_page_last               5057
_journal_paper_doi               10.1021/acs.joc.8b00390
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H17 N O2'
_chemical_formula_sum            'C11 H17 N O2'
_chemical_formula_weight         195.25
_chemical_name_systematic
;
(6S,9aS)-6-Hydroxymethyl-8-methyl-1,2,3,6,9,9a-hexahydroquinolizin-4(4H)-one 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9924(4)
_cell_length_b                   10.8848(5)
_cell_length_c                   12.0467(5)
_cell_measurement_reflns_used    5122
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.52
_cell_volume                     1048.01(8)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.806
_diffrn_reflns_theta_min         2.522
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.42
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0.8571
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 978 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.0725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                2472
_reflns_number_total             2558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00390_si_002.cif
_cod_data_source_block           compound13
_cod_database_code               4035517
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              26012
_shelx_hkl_checksum              3119