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_4126038
_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         'C18 H24 Cl N O4'
_chemical_formula_sum            'C18 H24 Cl N O4'
_chemical_formula_weight         353.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.061(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4830(3)
_cell_length_b                   13.0673(7)
_cell_length_c                   17.5715(8)
_cell_measurement_reflns_used    1222
_cell_measurement_temperature    294.09(10)
_cell_measurement_theta_max      24.9580
_cell_measurement_theta_min      3.6050
_cell_volume                     1717.89(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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      294.09(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -49.00   55.40   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  -60.0000 72

  2 omega  -10.00   16.10   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -180.0000 18

  3 omega   -6.00   23.00   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   57.0000 -120.0000 20

  4 omega    0.00   78.30   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 54
;
_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      -0.0316210000
_diffrn_orient_matrix_UB_12      0.0377172000
_diffrn_orient_matrix_UB_13      0.0254673000
_diffrn_orient_matrix_UB_21      -0.0328361000
_diffrn_orient_matrix_UB_22      -0.0390432000
_diffrn_orient_matrix_UB_23      0.0240485000
_diffrn_orient_matrix_UB_31      0.0831489000
_diffrn_orient_matrix_UB_32      -0.0010917000
_diffrn_orient_matrix_UB_33      0.0200352000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6549
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0464P)^2^+0.6252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                2007
_reflns_number_total             3380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b03280_si_010.cif
_cod_data_source_block           zhaoxh_0904
_cod_depositor_comments
'Adding full bibliography for 4126037--4126039.cif.'
_cod_database_code               4126038
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.078) H1B(0.078) H2A(0.083) H2B(0.083) H3A(0.069) H3B(0.069)
 H4(0.049) H6A(0.057) H6B(0.057) H7(0.046) H10A(0.047) H10B(0.047) H11(0.052)
 H12A(0.053) H12B(0.053) H13A(0.096) H13B(0.096) H13C(0.096) H16A(0.047)
 H16B(0.047) H17A(0.064) H17B(0.064) H18A(0.073) H18B(0.073)
 Fixed X: H1A(-0.0978) H1B(-0.0983) H2A(0.1918) H2B(0.0973) H3A(0.22)
 H3B(0.3767) H4(0.3601) H6A(0.5891) H6B(0.5652) H7(0.3803) H10A(-0.0465)
 H10B(0.0407) H11(0.2805) H12A(0.3223) H12B(0.1415) H13A(-0.042) H13B(0.1332)
 H13C(0.0349) H16A(0.4285) H16B(0.2412) H17A(0.207) H17B(0.3706) H18A(0.4027)
 H18B(0.564)
 Fixed Y: H1A(1.1745) H1B(1.2076) H2A(1.2199) H2B(1.3121) H3A(1.2648)
 H3B(1.2752) H4(1.1) H6A(0.9656) H6B(1.0017) H7(0.8572) H10A(1.0491)
 H10B(1.1578) H11(1.1062) H12A(0.9383) H12B(0.9054) H13A(1.0385) H13B(1.0587)
 H13C(1.1497) H16A(0.9394) H16B(0.9361) H17A(0.7652) H17B(0.7657) H18A(0.7974)
 H18B(0.7914)
 Fixed Z: H1A(0.4421) H1B(0.3563) H2A(0.459) H2B(0.4178) H3A(0.3016)
 H3B(0.3621) H4(0.3861) H6A(0.2928) H6B(0.2084) H7(0.2477) H10A(0.2335)
 H10B(0.238) H11(0.1671) H12A(0.1309) H12B(0.1673) H13A(0.0968) H13B(0.0516)
 H13C(0.0911) H16A(0.3953) H16B(0.4336) H17A(0.4069) H17B(0.3522) H18A(0.5096)
 H18B(0.454)
;
_olex2_date_sample_data_collection 2016-09-05
_olex2_submission_special_instructions 'No special instructions were received'