Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D.
Wang, Fang-Xin; Du, Ji-Yuan; Wang, Hui-Bin; Zhang, Peng-Lin; Zhang, Guo-Biao; Yu, Ke-Yin; Zhang, Xiang-Zhi; An, Xian-Tao; Cao, Ye-Xing; Fan, Chun-An; Journal of the American Chemical Society 139 (2017) 4282–4285; doi:10.1021/jacs.6b13401

data_4125854
_publ_section_title
;
 Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4282
_journal_page_last               4285
_journal_paper_doi               10.1021/jacs.6b13401
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C27 H36 O8'
_chemical_formula_sum            'C27 H36 O8'
_chemical_formula_weight         488.56
_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
_audit_creation_date             2016-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                83.811(6)
_cell_angle_beta                 75.257(6)
_cell_angle_gamma                80.638(6)
_cell_formula_units_Z            4
_cell_length_a                   12.3565(9)
_cell_length_b                   15.4538(10)
_cell_length_c                   17.0147(12)
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    294.63(10)
_cell_measurement_theta_max      23.0490
_cell_measurement_theta_min      3.4050
_cell_volume                     3092.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.63(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0397565000
_diffrn_orient_matrix_UB_12      0.0236580000
_diffrn_orient_matrix_UB_13      0.0086137000
_diffrn_orient_matrix_UB_21      -0.0366440000
_diffrn_orient_matrix_UB_22      0.0398807000
_diffrn_orient_matrix_UB_23      -0.0034137000
_diffrn_orient_matrix_UB_31      -0.0259038000
_diffrn_orient_matrix_UB_32      -0.0049253000
_diffrn_orient_matrix_UB_33      0.0422064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26687
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.970
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         12158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0811
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2339
_refine_ls_wR_factor_ref         0.2564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6275
_reflns_number_total             12158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13401_si_006.cif
_cod_data_source_block           wangfx0429
_cod_depositor_comments
'Adding full bibliography for 4125854--4125856.cif.'
_cod_database_code               4125854
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Sof: C52B(0.5) H52A(0.5) H52B(0.5) C53B(0.6) H53A(0.6) H53B(0.6)
 H53C(0.6) C52A(0.5) H52C(0.5) H52D(0.5) C53A(0.4) H53D(0.4) H53E(0.4) H53F(0.4)
 Fixed Uiso: H14(0.122) H30A(0.078) H30B(0.078) H31(0.098) H32A(0.121)
 H32B(0.121) H33(0.084) H35A(0.093) H35B(0.093) H37A(0.104) H37B(0.104)
 H39A(0.066) H39B(0.066) H40A(0.088) H40B(0.088) H41A(0.099) H41B(0.099)
 H44(0.086) H45(0.107) H46(0.098) H47(0.11) H48(0.091) H49(0.064) H50A(0.077)
 H50B(0.077) H51A(0.087) H51B(0.087) H54A(0.143) H54B(0.143) H55A(0.114)
 H55B(0.114) H52A(0.095) H52B(0.095) H53A(0.188) H53B(0.188) H53C(0.188)
 H52C(0.104) H52D(0.104) H53D(0.188) H53E(0.188) H53F(0.188) H6(0.121)
 H3A(0.079) H3B(0.079) H4(0.069) H6A(0.064) H6B(0.064) H7(0.077) H8A(0.09)
 H8B(0.09) H9A(0.085) H9B(0.085) H12A(0.057) H12B(0.057) H13A(0.075)
 H13B(0.075) H14A(0.079) H14B(0.079) H17(0.099) H18(0.126) H19(0.114)
 H20(0.109) H21(0.085) H22(0.055) H23A(0.063) H23B(0.063) H24A(0.08) H24B(0.08)
 H25A(0.08) H25B(0.08) H26A(0.174) H26B(0.174) H26C(0.174) H27A(0.095)
 H27B(0.095) H28A(0.151) H28B(0.151)
 Fixed X: H14(0.7662) H30A(0.5919) H30B(0.5907) H31(0.4106) H32A(0.4071)
 H32B(0.3109) H33(0.3925) H35A(0.5415) H35B(0.563) H37A(0.3145) H37B(0.4319)
 H39A(0.6111) H39B(0.5573) H40A(0.4467) H40B(0.385) H41A(0.5803) H41B(0.457)
 H44(0.4729) H45(0.4634) H46(0.5356) H47(0.6128) H48(0.6229) H49(0.6663)
 H50A(0.7696) H50B(0.8614) H51A(0.8977) H51B(0.8488) H54A(0.2273) H54B(0.2604)
 H55A(0.4094) H55B(0.3683) H52A(0.9006) H52B(0.8465) H53A(0.7056) H53B(0.7365)
 H53C(0.6393) H52C(0.7617) H52D(0.6684) H53D(0.9516) H53E(0.9435) H53F(0.9674)
 H6(1.2152) H3A(1.2473) H3B(1.115) H4(1.13) H6A(1.322) H6B(1.2737) H7(1.3696)
 H8A(1.2806) H8B(1.3404) H9A(1.2247) H9B(1.2086) H12A(0.9138) H12B(0.9619)
 H13A(0.9514) H13B(0.9182) H14A(0.7795) H14B(0.7594) H17(0.4158) H18(0.3286)
 H19(0.4247) H20(0.611) H21(0.7048) H22(1.0788) H23A(1.2341) H23B(1.1256)
 H24A(1.1988) H24B(1.0873) H25A(0.8981) H25B(0.8185) H26A(0.8236) H26B(0.7879)
 H26C(0.9116) H27A(0.8822) H27B(0.9998) H28A(1.0078) H28B(0.9016)
 Fixed Y: H14(0.4831) H30A(0.7722) H30B(0.6726) H31(0.7377) H32A(0.8809)
 H32B(0.8434) H33(0.8896) H35A(0.946) H35B(0.9413) H37A(0.6797) H37B(0.6198)
 H39A(0.8089) H39B(0.7271) H40A(0.903) H40B(0.8223) H41A(0.8592) H41B(0.8864)
 H44(0.6036) H45(0.4657) H46(0.4265) H47(0.5254) H48(0.6663) H49(0.6168)
 H50A(0.6872) H50B(0.6803) H51A(0.5531) H51B(0.5263) H54A(0.6378) H54B(0.6708)
 H55A(0.5768) H55B(0.5366) H52A(0.617) H52B(0.6434) H53A(0.6105) H53B(0.5103)
 H53C(0.5415) H52C(0.6311) H52D(0.5994) H53D(0.5388) H53E(0.6) H53F(0.4977)
 H6(1.029) H3A(0.5607) H3B(0.5622) H4(0.6191) H6A(0.7383) H6B(0.8373)
 H7(0.7785) H8A(0.6732) H8B(0.6347) H9A(0.8296) H9B(0.8911) H12A(0.7716)
 H12B(0.6896) H13A(0.5975) H13B(0.6777) H14A(0.637) H14B(0.6122) H17(0.8325)
 H18(0.9683) H19(1.0742) H20(1.0337) H21(0.8939) H22(0.886) H23A(0.8134)
 H23B(0.8152) H24A(0.9424) H24B(0.9709) H25A(0.8991) H25B(0.8565) H26A(0.9904)
 H26B(0.9012) H26C(0.9045) H27A(0.9412) H27B(0.9673) H28A(0.8672) H28B(0.8312)
 Fixed Z: H14(-0.2614) H30A(-0.251) H30B(-0.2217) H31(-0.2348) H32A(-0.2047)
 H32B(-0.1368) H33(-0.051) H35A(-0.1753) H35B(-0.0874) H37A(-0.1075) H37B(-
 0.1313) H39A(0.0023) H39B(0.0476) H40A(0.0576) H40B(0.098) H41A(0.141)
 H41B(0.1937) H44(0.223) H45(0.2879) H46(0.3994) H47(0.4497) H48(0.386) H49(-
 0.1057) H50A(-0.2458) H50B(-0.1958) H51A(-0.2616) H51B(-0.1691) H54A(0.0502)
 H54B(0.1243) H55A(0.1081) H55B(0.0415) H52A(-0.0702) H52B(0.0189) H53A(0.0978)
 H53B(0.1216) H53C(0.0766) H52C(0.0528) H52D(0.0212) H53D(0.0248) H53E(-0.0539)
 H53F(-0.0584) H6(0.2471) H3A(0.406) H3B(0.4291) H4(0.5416) H6A(0.3421)
 H6B(0.3554) H7(0.4556) H8A(0.5542) H8B(0.4697) H9A(0.5675) H9B(0.4903)
 H12A(0.4852) H12B(0.4345) H13A(0.5511) H13B(0.6058) H14A(0.5107) H14B(0.605)
 H17(0.5807) H18(0.6118) H19(0.6329) H20(0.6437) H21(0.6113) H22(0.3554)
 H23A(0.2383) H23B(0.2061) H24A(0.1529) H24B(0.2188) H25A(0.4069) H25B(0.3686)
 H26A(0.203) H26B(0.2469) H26C(0.1943) H27A(0.5949) H27B(0.5962) H28A(0.6916)
 H28B(0.6792)
;
_shelx_res_checksum              94684
_shelx_hkl_checksum              26623
_olex2_submission_special_instructions 'No special instructions were received'