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_4133797
_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 rm
_chemical_formula_moiety         'C29 H39 F O5'
_chemical_formula_sum            'C29 H39 F O5'
_chemical_formula_weight         486.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7910(3)
_cell_length_b                   20.3109(8)
_cell_length_c                   26.9659(9)
_cell_measurement_reflns_used    7231
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      23.3140
_cell_measurement_theta_min      2.4320
_cell_volume                     5910.2(3)
_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      180.00(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27988
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.143
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_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     637
_refine_ls_number_reflns         11333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0771
_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^)+(0.1423P)^2^+0.5958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                7850
_reflns_number_total             11333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11872_si_005.cif
_cod_data_source_block           3_sq
_cod_database_code               4133797
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.958
_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. Uiso/Uaniso restraints and constraints
Uanis(C39) = Uanis(C38)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17), C18(H18), C23(H23), C24(H24), C38(H38), C46(H46), C47(H47),
 C52(H52), C53(H53)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C14(H14a,H14b), C15(H15a,H15b), C21(H21a,H21b),
 C22(H22a,H22b), C25(H25a,H25b), C36(H36a,H36b), C37(H37a,H37b), C43(H43a,H43b),
  C44(H44a,H44b), C50(H50a,H50b), C51(H51a,H51b), C54(H54a,H54b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2a), C3(H3a), C5(H5), C6(H6), C11(H11), C31(H31), C32(H32), C34(H34),
 C35(H35), C40(H40)
3.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C13(H13a,H13b,H13c), C28(H28a,H28b,H28c), C29(H29a,H29b,
 H29c), C39(H39a,H39b,H39c), C42(H42a,H42b,H42c), C57(H57a,H57b,H57c), C58(H58a,
 H58b,H58c)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O7(H7), O8(H8)
3.f :
 C20(H20), C49(H49)
;
_shelx_res_checksum              66426
_shelx_hkl_checksum              7420
_shelx_fab_checksum              13902
_olex2_submission_special_instructions 'No special instructions were received'