Total Synthesis of (±)-Lycojaponicumin D and Lycodoline-Type Lycopodium Alkaloids.
Zhao, Xian-He; Zhang, Qing; Du, Ji-Yuan; Lu, Xin-Yun; Cao, Ye-Xing; Deng, Yu-Hua; Fan, Chun-An; Journal of the American Chemical Society 139 (2017) 7095–7103; doi:10.1021/jacs.7b03280

data_4126039
_publ_section_title
;
 Total Synthesis of (+-)-Lycojaponicumin D and Lycodoline-Type Lycopodium
 Alkaloids.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7095
_journal_page_last               7103
_journal_paper_doi               10.1021/jacs.7b03280
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.414(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8530(9)
_cell_length_b                   7.9767(5)
_cell_length_c                   16.4717(16)
_cell_measurement_reflns_used    636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9850
_cell_measurement_theta_min      3.6350
_cell_volume                     1360.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -46.00   12.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 29

  2 omega  -33.00   27.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   60.0000 30

  3 omega   40.00   70.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 15

  4 omega   14.00   92.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0039486000
_diffrn_orient_matrix_UB_12      0.0392932000
_diffrn_orient_matrix_UB_13      0.0377719000
_diffrn_orient_matrix_UB_21      0.0683568000
_diffrn_orient_matrix_UB_22      0.0017932000
_diffrn_orient_matrix_UB_23      0.0157864000
_diffrn_orient_matrix_UB_31      0.0003734000
_diffrn_orient_matrix_UB_32      0.0797549000
_diffrn_orient_matrix_UB_33      -0.0190007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4803
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1979
_reflns_number_gt                1331
_reflns_number_total             2675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b03280_si_005.cif
_cod_data_source_block           zhxh_1102
_cod_depositor_comments
'Adding full bibliography for 4126037--4126039.cif.'
_cod_database_code               4126039
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.065) H0AA(0.047) H0AB(0.047) H1A(0.059) H1B(0.059)
 H2A(0.061) H2B(0.061) H3A(0.056) H3B(0.056) H6(0.043) H7A(0.058) H7B(0.058)
 H8A(0.063) H8B(0.063) H9A(0.058) H9B(0.058) H11A(0.06) H11B(0.06) H12(0.05)
 H13A(0.06) H13B(0.06) H14(0.054) H15A(0.101) H15B(0.101) H15C(0.101)
 Fixed X: H2(0.2624) H0AA(0.5481) H0AB(0.4424) H1A(0.2741) H1B(0.1652)
 H2A(0.1105) H2B(0.1167) H3A(0.3165) H3B(0.2283) H6(0.4639) H7A(0.632)
 H7B(0.6378) H8A(0.4301) H8B(0.5187) H9A(0.4314) H9B(0.3161) H11A(0.6295)
 H11B(0.5122) H12(0.4277) H13A(0.4887) H13B(0.6149) H14(0.6736) H15A(0.6923)
 H15B(0.7217) H15C(0.5877)
 Fixed Y: H2(0.2933) H0AA(0.6793) H0AB(0.6081) H1A(0.5513) H1B(0.6545)
 H2A(0.3693) H2B(0.4299) H3A(0.2507) H3B(0.176) H6(0.4383) H7A(0.6112)
 H7B(0.6832) H8A(0.7272) H8B(0.8711) H9A(0.8456) H9B(0.8645) H11A(0.1113)
 H11B(0.1207) H12(0.1123) H13A(0.2843) H13B(0.2044) H14(0.4466) H15A(0.6343)
 H15B(0.4512) H15C(0.5335)
 Fixed Z: H2(0.2788) H0AA(0.2743) H0AB(0.3119) H1A(0.0284) H1B(0.0501)
 H2A(0.0324) H2B(0.1243) H3A(0.084) H3B(0.1353) H6(0.0825) H7A(0.08)
 H7B(0.1697) H8A(0.0189) H8B(0.07) H9A(0.1814) H9B(0.0979) H11A(0.229)
 H11B(0.146) H12(0.2572) H13A(0.3741) H13B(0.3636) H14(0.3125) H15A(0.4251)
 H15B(0.4601) H15C(0.453)
;
_olex2_date_sample_data_collection 2016-11-02
_olex2_submission_special_instructions 'No special instructions were received'