Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine.
Kou, Kevin G. M.; Li, Beryl X.; Lee, Jack C.; Gallego, Gary M.; Lebold, Terry P.; DiPasquale, Antonio G.; Sarpong, Richmond; Journal of the American Chemical Society 138 (2016) 10830–10833; doi:10.1021/jacs.6b07268

data_4130828
_publ_section_title
;
 Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine,
 N-Ethyl-1\a-hydroxy-17-veratroyldictyzine, and Paniculamine.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10830
_journal_page_last               10833
_journal_paper_doi               10.1021/jacs.6b07268
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C31 H38 N2 O11 S'
_chemical_formula_weight         646.69
_chemical_name_common            JL-III-050B
_chemical_name_systematic
; 
 sarpong84 
;
_space_group.centring_type       primitive
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 110.575(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4739(6)
_cell_length_b                   16.2599(7)
_cell_length_c                   14.1217(6)
_cell_measurement_reflns_used    9160
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.25
_cell_volume                     3111.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            83189
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         3.261
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         5700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0555P)^2^+2.8784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4978
_reflns_number_total             5700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07268_si_001.cif
_cod_data_source_block           sarpong84
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4130828
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.971
_shelxl_version_number           2014-3
_shelx_res_checksum              49271
_shelx_hkl_checksum              97446