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_4126037
_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 H23 N O3'
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                91.404(18)
_cell_angle_beta                 104.88(2)
_cell_angle_gamma                116.48(2)
_cell_formula_units_Z            2
_cell_length_a                   8.499(3)
_cell_length_b                   9.1139(17)
_cell_length_c                   10.798(3)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    293.8(3)
_cell_measurement_theta_max      27.3640
_cell_measurement_theta_min      3.8850
_cell_volume                     714.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      293.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    0.00   93.60   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 48

  2 omega   13.00   53.95   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   77.0000   60.0000 21

  3 omega   46.00   86.95   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 21

  4 omega  -47.00   46.60   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -180.0000 48

  5 omega  -18.00   65.85   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   60.0000 43

  6 omega   -5.00   24.25   1.9500    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0700802000
_diffrn_orient_matrix_UB_12      -0.0166104000
_diffrn_orient_matrix_UB_13      0.0299377000
_diffrn_orient_matrix_UB_21      0.0557855000
_diffrn_orient_matrix_UB_22      0.0778055000
_diffrn_orient_matrix_UB_23      0.0413733000
_diffrn_orient_matrix_UB_31      -0.0390368000
_diffrn_orient_matrix_UB_32      0.0378212000
_diffrn_orient_matrix_UB_33      -0.0461924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4522
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0455P)^2^+0.2757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                1733
_reflns_number_total             2817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b03280_si_006.cif
_cod_data_source_block           zhaoxh_0725
_cod_depositor_comments
'Adding full bibliography for 4126037--4126039.cif.'
_cod_original_cell_volume        714.2(3)
_cod_database_code               4126037
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.096) H3(0.066) H5A(0.057) H5B(0.057) H6(0.049) H8A(0.053)
 H8B(0.053) H9A(0.059) H9B(0.059) H10A(0.05) H10B(0.05) H11A(0.048) H11B(0.048)
 H12A(0.054) H12B(0.054) H13A(0.053) H13B(0.053) H14(0.045) H15A(0.041)
 H15B(0.041) H16A(0.082) H16B(0.082) H16C(0.082)
 Fixed X: H1(0.6739) H3(1.0234) H5A(0.764) H5B(0.9381) H6(0.9984) H8A(0.7106)
 H8B(0.6421) H9A(0.7318) H9B(0.5317) H10A(0.655) H10B(0.6057) H11A(0.7932)
 H11B(0.9977) H12A(0.8744) H12B(0.6758) H13A(1.2358) H13B(1.2728) H14(1.1553)
 H15A(1.2204) H15B(1.1654) H16A(1.5005) H16B(1.4676) H16C(1.4404)
 Fixed Y: H1(0.6113) H3(0.6741) H5A(0.9054) H5B(1.0244) H6(0.9773) H8A(0.7432)
 H8B(0.6453) H9A(0.52) H9B(0.4542) H10A(0.2773) H10B(0.3493) H11A(0.2125)
 H11B(0.3376) H12A(0.3724) H12B(0.3002) H13A(1.0678) H13B(0.9894) H14(0.8256)
 H15A(0.6875) H15B(0.596) H16A(0.9315) H16B(1.0034) H16C(0.8213)
 Fixed Z: H1(-0.1291) H3(0.5121) H5A(0.2046) H5B(0.168) H6(0.3795) H8A(0.4117)
 H8B(0.2707) H9A(0.5018) H9B(0.4069) H10A(0.3724) H10B(0.2464) H11A(0.232)
 H11B(0.2392) H12A(0.0385) H12B(0.0557) H13A(0.279) H13B(0.4039) H14(0.1464)
 H15A(0.3746) H15B(0.2335) H16A(0.334) H16B(0.2049) H16C(0.2)
;
_olex2_date_sample_data_collection 2016-07-25
_olex2_submission_special_instructions 'No special instructions were received'