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_4130831
_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            'C22 H27 N O4'
_chemical_formula_weight         369.44
_chemical_name_common            KK3-129-4
_chemical_name_systematic        sarpong133
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.255(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7056(5)
_cell_length_b                   19.1395(13)
_cell_length_c                   14.5164(10)
_cell_measurement_reflns_used    9532
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      68.05
_cell_measurement_theta_min      3.85
_cell_volume                     1843.8(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
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_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42683
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_min         3.847
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       rod
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0407P)^2^+2.5063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3020
_reflns_number_total             3345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07268_si_003.cif
_cod_data_source_block           sarpong133
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4130831
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              84423
_shelx_hkl_checksum              17607