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_4130830
_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            'C25 H35 N O6'
_chemical_formula_weight         445.54
_chemical_name_common            KK2-075
_chemical_name_systematic        sarpong121
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 109.488(2)
_cell_angle_gamma                90
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_cell_length_a                   23.9341(8)
_cell_length_b                   11.7122(4)
_cell_length_c                   16.9699(5)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.50
_cell_volume                     4484.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
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_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47019
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         1.805
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
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_exptl_crystal_size_mid          0.060
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_refine_diff_density_max         0.989
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0757P)^2^+8.9913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1549
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_reflns_number_gt                3380
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07268_si_002.cif
_cod_data_source_block           sarpong121
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4130830
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              78962
_shelx_hkl_checksum              5805