Asymmetric Total Synthesis of Pre-schisanartanin C.
Jiang, Yan-Long; Yu, Hai-Xin; Li, Yong; Qu, Pei; Han, Yi-Xin; Chen, Jia-Hua; Yang, Zhen; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b11872

data_4133798
_publ_section_title
;
 Asymmetric Total Synthesis of Pre-schisanartanin C.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11872
_journal_year                    2019
_chemical_formula_moiety         'C20 H26 O5'
_chemical_formula_sum            'C20 H26 O5'
_chemical_formula_weight         346.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                91.043(3)
_cell_angle_beta                 100.782(3)
_cell_angle_gamma                100.374(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1450(2)
_cell_length_b                   11.7309(3)
_cell_length_c                   12.9688(4)
_cell_measurement_reflns_used    4970
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.9170
_cell_measurement_theta_min      5.0190
_cell_volume                     1048.85(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -85.00  72.00   1.00    1.00    --    0.00  43.00  60.00  157
  2  \w    -86.00 -57.00   1.00    1.00    --    0.00  55.00-180.00   29
  3  \w    -49.00 -20.00   1.00    1.00    --  -90.00  55.00-150.00   29
  4  \w   -179.00 -81.00   1.00    1.00    --  -90.00  55.00 -60.00   98
  5  \w    -77.00 -16.00   1.00    1.00    --  -90.00  55.00 -60.00   61
  6  \w   -170.00 -67.00   1.00    1.00    --  -90.00  55.00  30.00  103
  7  \w   -103.00  -2.00   1.00    1.00    --  -90.00  29.00-120.00  101
  8  \w   -144.00-118.00   1.00    1.00    --  -90.00  29.00-120.00   26
  9  \w   -171.00 -80.00   1.00    1.00    --  -90.00  55.00 120.00   91
 10  \w   -172.00 -97.00   1.00    1.00    --  -90.00  55.00-150.00   75
 11  \w   -175.00-150.00   1.00    1.00    --  -90.00  55.00 -30.00   25
 12  \w    -74.00 -48.00   1.00    1.00    --  -90.00  55.00 -30.00   26
 13  \w   -157.00-130.00   1.00    1.00    --  -90.00  55.00  60.00   27
 14  \w    -50.00 -24.00   1.00    1.00    --  -90.00  55.00  60.00   26
 15  \w   -141.00 -10.00   1.00    1.00    --  -90.00  29.00   0.00  131
 16  \w    -26.00   2.00   1.00    1.00    --    0.00  55.00-180.00   28
 17  \w    -66.00 -40.00   1.00    1.00    --  -90.00  29.00  90.00   26
 18  \w   -166.00-131.00   1.00    1.00    --  -90.00  29.00  90.00   35
 19  \w   -178.00-152.00   1.00    1.00    --  -90.00  55.00-120.00   26
 20  \w   -174.00-148.00   1.00    1.00    --  -90.00  55.00 -30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1255730000
_diffrn_orient_matrix_UB_12      -0.0486097000
_diffrn_orient_matrix_UB_13      -0.0681284000
_diffrn_orient_matrix_UB_21      0.1159482000
_diffrn_orient_matrix_UB_22      -0.0438851000
_diffrn_orient_matrix_UB_23      0.0987921000
_diffrn_orient_matrix_UB_31      -0.1438913000
_diffrn_orient_matrix_UB_32      -0.1165626000
_diffrn_orient_matrix_UB_33      -0.0162418000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9065
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.202
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.097
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+0.4830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3146
_reflns_number_total             3799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11872_si_004.cif
_cod_data_source_block           jyl2647a
_cod_original_cell_volume        1048.85(6)
_cod_database_code               4133798
_shelxl_version_number           2014-3
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.e :
 C17(H17)
;
_shelx_res_checksum              454
_shelx_hkl_checksum              12845
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.724
_oxdiff_exptl_absorpt_empirical_full_min 0.549