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_4033818
_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
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.415(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9684(2)
_cell_length_b                   12.1357(3)
_cell_length_c                   11.6184(3)
_cell_measurement_reflns_used    6428
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4550
_cell_measurement_theta_min      5.1960
_cell_volume                     1679.98(7)
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.971
_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    -22.00  23.00   0.50    0.50    --   -0.90  34.00  48.00   90
  2  \w    -90.00 -64.00   0.50    0.50    --   -0.90  34.00  48.00   52
  3  \w   -175.00-149.00   0.50    1.77    --  -98.40  34.00  48.00   52
  4  \w     38.00  87.00   0.50    0.50    --   -0.90  60.00 120.00   98
  5  \w    -64.00 -38.00   0.50    0.50    --    0.90  14.00 150.00   52
  6  \w      5.00  43.00   0.50    0.50    --    0.90  14.00 150.00   76
  7  \w     35.00  93.00   0.50    1.77    --    5.00  57.00   0.00  116
  8  \w    -19.00   6.00   0.50    1.77    --    5.00  34.00  48.00   50
  9  \w   -187.00  -9.00   0.50    1.77    --  -98.40  29.00  90.00  356
 10  \w   -177.00-151.00   0.50    1.77    --  -98.40  60.00 120.00   52
 11  \w   -139.00-113.00   0.50    1.77    --  -98.40  14.00  60.00   52
 12  \w   -188.00 -44.00   0.50    1.77    --  -98.40  57.00 150.00  288
 13  \w    -84.00 -10.00   0.50    1.77    --  -98.40  14.00  60.00  148
 14  \w   -187.00-161.00   0.50    1.77    --  -98.40  14.00  60.00   52
 15  \w   -181.00 -58.00   0.50    1.77    --  -98.40  43.00 150.00  246
 16  \w   -128.00-102.00   0.50    1.77    --  -98.40  58.00 170.77   52
 17  \w    -63.00 -38.00   0.50    1.77    --  -98.40  60.00 120.00   50
 18  \w   -100.00 -74.00   0.50    1.77    --  -98.40  34.00  48.00   52
;
_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      -0.0872702000
_diffrn_orient_matrix_UB_12      -0.0521783000
_diffrn_orient_matrix_UB_13      0.0728247000
_diffrn_orient_matrix_UB_21      0.0635678000
_diffrn_orient_matrix_UB_22      0.0464520000
_diffrn_orient_matrix_UB_23      0.1107716000
_diffrn_orient_matrix_UB_31      -0.0710481000
_diffrn_orient_matrix_UB_32      0.1060258000
_diffrn_orient_matrix_UB_33      -0.0130314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9206
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.808
_diffrn_reflns_theta_min         3.710
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73782
_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    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0437P)^2^+2.5863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3034
_reflns_number_total             3297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01589_si_002.cif
_cod_data_source_block           180429ks
_cod_database_code               4033818
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C68 H104 O12 S4 '
_reflns_odcompleteness_completeness 99.75
_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), C10(H10), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C6(H6a,H6b), C4(H4a,H4b), C14(H14a,H14b)
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              59138
_shelx_hkl_checksum              4697
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.497