Formal Syntheses of (-)-Lepadiformines A, C, and (-)-Fasicularin.
Takashima, Katsuki; Hayakawa, Daichi; Gouda, Hiroaki; Toyooka, Naoki; The Journal of organic chemistry 84 (2019) 5222–5229; doi:10.1021/acs.joc.9b00071

data_4034310
_publ_section_title
;
 Formal Syntheses of (-)-Lepadiformines A, C, and (-)-Fasicularin.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5222
_journal_page_last               5229
_journal_paper_doi               10.1021/acs.joc.9b00071
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C11 H13 N O3'
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.496(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.35354(15)
_cell_length_b                   5.87211(11)
_cell_length_c                   11.1184(2)
_cell_measurement_reflns_used    5383
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      4.00
_cell_volume                     477.894(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5415
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.193
_diffrn_reflns_theta_min         3.994
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             220.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details
;
 Flack x determined using 634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.1025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1567
_reflns_number_total             1695
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b00071_si_002.cif
_cod_data_source_block           takashima_0827
_cod_original_cell_volume        477.895(17)
_cod_database_code               4034310
_shelx_res_checksum              51950
_shelx_hkl_checksum              6912