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_4133800
_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_absolute_configuration syn
_chemical_formula_moiety         'C24 H36 O7'
_chemical_formula_sum            'C24 H36 O7'
_chemical_formula_weight         436.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.454(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.17331(19)
_cell_length_b                   10.2803(2)
_cell_length_c                   13.2668(3)
_cell_measurement_reflns_used    6313
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      68.6940
_cell_measurement_theta_min      3.3140
_cell_volume                     1107.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      160
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_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    -90.00  73.00   1.00    1.00    --    0.00   0.00 120.00  163
  2  \w   -135.00  15.00   1.00    2.00    --  -45.00  55.00   0.00  150
  3  \w   -132.00  31.00   1.00    2.00    --  -45.00  55.00  60.00  163
  4  \w   -135.00  15.00   1.00    2.00    --  -45.00  30.00 120.00  150
  5  \w   -180.00  -9.00   1.00    8.00    --  -90.00  55.00 180.00  171
  6  \w   -180.00  -2.00   1.00    8.00    --  -90.00  30.00 300.00  178
  7  \w   -180.00  -1.00   1.00    8.00    --  -90.00  55.00 120.00  179
  8  \w   -140.00 -22.00   1.00    8.00    --  -90.00  30.00  60.00  118
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1457254000
_diffrn_orient_matrix_UB_12      0.0343709000
_diffrn_orient_matrix_UB_13      0.0793171000
_diffrn_orient_matrix_UB_21      0.1164827000
_diffrn_orient_matrix_UB_22      -0.0003693000
_diffrn_orient_matrix_UB_23      -0.0835836000
_diffrn_orient_matrix_UB_31      -0.0344715000
_diffrn_orient_matrix_UB_32      0.1459348000
_diffrn_orient_matrix_UB_33      -0.0189880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9863
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.423
_diffrn_reflns_theta_min         3.353
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.92
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0031(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0840P)^2^+0.6620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.725
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                3372
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11872_si_006.cif
_cod_data_source_block           '_783triol'
_cod_original_cell_volume        1107.66(4)
_cod_database_code               4133800
_reflns_odcompleteness_completeness 98.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.30
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00L(H00L), C00O(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00G(H00C,H00D), C00K(H00G,H00J), C00M(H00K,H00M), C00N(H00N,
 H00O), C00P(H00Q,H00R)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E)
2.d Idealised Me refined as rotating group:
 C00R(H00S,H00T,H00U), C00S(H00V,H00W,H00X), C00T(H00Y,H,HA), C00U(H00Z,HB,HC),
  C00V(H00,HD,HE)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O004(H004), O006(H006)
;
_shelx_res_checksum              97842
_shelx_hkl_checksum              57298
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.472