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_4130829
_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_absolute_configuration ad
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.44
_chemical_name_common            KK3-106-3
_chemical_name_systematic        sarpong132
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 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                 103.504(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5745(6)
_cell_length_b                   17.2047(12)
_cell_length_c                   12.0212(8)
_cell_measurement_reflns_used    9330
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      2.57
_cell_volume                     1925.5(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-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0449
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            57510
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.372
_diffrn_reflns_theta_min         2.568
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 2855 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6510
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.3734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0760
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.844
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                6433
_reflns_number_total             6510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07268_si_005.cif
_cod_data_source_block           sarpong132
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4130829
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              55651
_shelx_hkl_checksum              31022