Toward the Total Synthesis of Scabrosins: Synthesis of a Desulfur-scabrosin Skeleton and Its Stereoisomers.
Liu, Yuyin; Wang, Zhi-Peng; Banne, Sreenivas; Guo, Jian; He, Yun; The Journal of organic chemistry 84 (2019) 5838–5845; doi:10.1021/acs.joc.9b00015

data_4034319
_publ_section_title
;
 Toward the Total Synthesis of Scabrosins: Synthesis of a
 Desulfur-scabrosin Skeleton and Its Stereoisomers.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5838
_journal_page_last               5845
_journal_paper_doi               10.1021/acs.joc.9b00015
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H58 N2 O6 Si2'
_chemical_formula_sum            'C36 H58 N2 O6 Si2'
_chemical_formula_weight         671.02
_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
_audit_creation_date             2016-01-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.553(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2188(4)
_cell_length_b                   8.8154(3)
_cell_length_c                   16.5835(6)
_cell_measurement_reflns_used    3462
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.1240
_cell_measurement_theta_min      3.9530
_cell_volume                     1852.37(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9642
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.061
_diffrn_reflns_theta_min         3.392
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0655P)^2^+0.7738P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.548
_reflns_Friedel_fraction_full    0.698
_reflns_Friedel_fraction_max     0.536
_reflns_number_gt                5777
_reflns_number_total             7032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00015_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1852.38(11)
_cod_database_code               4034319
_shelxl_version_number           2013-2
_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:
 C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C011(H011), C018(H018)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00a,H00b), C00P(H00c,H00d)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00X(H00h,H00k,H00p), C00Y(H00x,H00y,H), C00Z(H00z,Ha,Hb), C010(H01a,H01b,
 H01c), C012(H01d,H01e,H01f), C013(H01g,H01h,H01i), C014(H01j,H01k,H01l),
 C015(H01m,H01n,H01o), C016(H01p,H01q,H01r), C017(H01s,H01t,H01u), C019(H01v,
 H01w,H01x), C01A(H01y,Hc,Hd)
;
_shelx_res_checksum              70870
_shelx_hkl_checksum              30268
_olex2_submission_special_instructions 'No special instructions were received'