Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and Echinocidins.
Shimoda, Kazuma; Yamaoka, Yousuke; Yoo, Dongeun; Yamada, Ken-Ichi; Takikawa, Hiroshi; Takasu, Kiyosei; The Journal of organic chemistry 84 (2019) 11014–11024; doi:10.1021/acs.joc.9b01589

data_4033819
_publ_section_title
;
 Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and
 Echinocidins.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11014
_journal_page_last               11024
_journal_paper_doi               10.1021/acs.joc.9b01589
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H26 O3 S'
_chemical_formula_sum            'C17 H26 O3 S'
_chemical_formula_weight         310.44
_chemical_name_systematic        KS
_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     dual
_audit_creation_date             2018-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                94.494(5)
_cell_angle_beta                 102.935(5)
_cell_angle_gamma                99.045(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3723(6)
_cell_length_b                   9.9567(7)
_cell_length_c                   10.2048(6)
_cell_measurement_reflns_used    5044
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.8540
_cell_measurement_theta_min      4.4780
_cell_volume                     813.06(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.945
_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     40.00  66.00   0.50    1.00    --    5.00  60.00 120.00   52
  2  \w    -39.00  33.00   0.50    1.00    --  -45.70  43.00   0.00  144
  3  \w   -130.00 -42.00   0.50    1.00    --  -45.70  43.00   0.00  176
  4  \w    -33.00  36.00   0.50    1.00    --  -45.70  29.00  30.00  138
  5  \w   -105.00 -40.00   0.50    1.00    --  -45.70  57.00 120.00  130
  6  \w   -134.00-104.00   0.50    1.00    --  -45.70  60.00  60.00   60
  7  \w   -100.00 -49.00   0.50    1.00    --  -45.70  60.00  60.00  102
  8  \w   -188.00 -65.00   0.50    1.50    -- -100.10  43.00   0.00  246
  9  \w    -47.00 -13.00   0.50    1.50    -- -100.10  43.00  30.00   68
 10  \w   -163.00-115.00   0.50    1.50    -- -100.10   0.00 120.00   96
 11  \w   -181.00-156.00   0.50    1.50    -- -100.10  60.00  90.00   50
 12  \w   -188.00 -54.00   0.50    1.50    -- -100.10  14.00 150.00  268
 13  \w    -45.00 -16.00   0.50    1.50    -- -100.10  14.00 150.00   58
 14  \w   -131.00 -48.00   0.50    1.50    -- -100.10  60.00 150.00  166
 15  \w   -188.00-135.00   0.50    1.50    -- -100.10  60.00 150.00  106
 16  \w   -136.00 -97.00   0.50    1.50    -- -100.10  57.00 120.00   78
 17  \w    -73.00 -48.00   0.50    1.50    -- -100.10  60.00  60.00   50
 18  \w   -151.00 -99.00   0.50    1.50    -- -100.10  60.00  60.00  104
 19  \w    -46.00 -13.00   0.50    1.50    -- -100.10  43.00   0.00   66
 20  \w   -110.00 -57.00   0.50    1.50    -- -100.10   0.00 120.00  106
 21  \w   -189.00 -35.00   0.50    1.50    -- -100.10  57.00   0.00  308
 22  \w   -160.00-134.00   0.50    1.50    -- -100.10  60.00  30.00   52
 23  \w   -189.00-136.00   0.50    1.50    -- -100.10  60.00   0.00  106
 24  \w   -150.00-125.00   0.50    1.50    -- -100.10  60.00  90.00   50
 25  \w   -160.00-129.00   0.50    1.50    -- -100.10  29.00   0.00   62
 26  \w    -57.00 -15.00   0.50    1.50    -- -100.10  29.00   0.00   84
 27  \w   -153.00 -41.00   0.50    1.50    -- -100.10  60.00 172.80  224
;
_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      0.1584431000
_diffrn_orient_matrix_UB_12      -0.0589148000
_diffrn_orient_matrix_UB_13      -0.0044561000
_diffrn_orient_matrix_UB_21      -0.0778601000
_diffrn_orient_matrix_UB_22      -0.0613048000
_diffrn_orient_matrix_UB_23      -0.1481898000
_diffrn_orient_matrix_UB_31      0.0752965000
_diffrn_orient_matrix_UB_32      0.1329067000
_diffrn_orient_matrix_UB_33      -0.0484859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8062
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.735
_diffrn_reflns_theta_min         4.477
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_preparation       recryst
_exptl_crystal_recrystallization_method recryst
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1267P)^2^+0.2464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01589_si_003.cif
_cod_data_source_block           exp_527
_cod_database_code               4033819
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H52 Cl2 O6 S1 '
_reflns_odcompleteness_completeness 97.65
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C4(H4A,H4B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O18(H18), O17(H17)
;
_shelx_res_checksum              6907
_shelx_hkl_checksum              74233
_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 2.667
_oxdiff_exptl_absorpt_empirical_full_min 0.302