Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N<sub>4</sub>-Oxide.
Kerkovius, Jeff K.; Kerr, Michael A.; Journal of the American Chemical Society 140 (2018) 8415–8419; doi:10.1021/jacs.8b05095

data_4132609
_publ_section_title
;
 Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4
 R)-Isodihydroukoumine N<sub>4</sub>-Oxide.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8415
_journal_page_last               8419
_journal_paper_doi               10.1021/jacs.8b05095
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C20 H27 N O6'
_chemical_formula_weight         377.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.090(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.816(3)
_cell_length_b                   18.649(4)
_cell_length_c                   11.003(2)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    110
_cell_measurement_theta_max      64.53
_cell_measurement_theta_min      4.55
_cell_volume                     1994.1(8)
_computing_cell_refinement       SAINT
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            60842
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.267
_diffrn_reflns_theta_max         66.267
_diffrn_reflns_theta_min         4.550
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.164
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0812
_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^)+(0.1573P)^2^+2.3562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2812
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05095_si_002.cif
_cod_data_source_block           n17122
_cod_original_cell_volume        1994.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4132609
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.714
_shelx_estimated_absorpt_t_max   0.885
_shelx_res_checksum              58440
_shelx_hkl_checksum              83287