Total Synthesis of Viridin and Viridiol.
Ji, Yang; Xin, Zhengyuan; He, Haibing; Gao, Shuanhu; Journal of the American Chemical Society 141 (2019) 16208–16212; doi:10.1021/jacs.9b08577

data_4127665
_publ_section_title
;
 Total Synthesis of Viridin and Viridiol.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16208
_journal_page_last               16212
_journal_paper_doi               10.1021/jacs.9b08577
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H48 O7 Si2'
_chemical_formula_sum            'C25 H48 O7 Si2'
_chemical_formula_weight         516.81
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-17
_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            4
_cell_length_a                   10.53270(10)
_cell_length_b                   12.80530(10)
_cell_length_c                   22.0965(2)
_cell_measurement_reflns_used    53369
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3810
_cell_measurement_theta_min      3.9910
_cell_volume                     2980.25(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -19.00  14.00   1.00    1.00    --    0.00  57.00  90.00   33
  2  \w     20.00  88.00   1.00    1.00    --    0.00  57.00  30.00   68
  3  \w    -23.00  86.00   1.00    1.00    --    0.00  57.00 -60.00  109
  4  \w    -23.00  44.00   1.00    1.00    --    0.00  57.00 150.00   67
  5  \w    -18.00  30.00   1.00    1.00    --    0.00  38.00   0.00   48
  6  \w     63.00  89.00   1.00    1.00    --    0.00  57.00 150.00   26
  7  \w    -22.00  11.00   1.00    1.00    --    0.00  57.00  30.00   33
  8  \w    -19.00  88.00   1.00    1.00    --    0.00  38.00-150.00  107
  9  \w     25.00  51.00   1.00    1.00    --    0.00  57.00  90.00   26
 10  \w    -31.00  58.00   1.00    1.00    --    0.00  82.00-120.00   89
 11  \w     35.00  85.00   1.00    1.00    --    0.00  38.00   0.00   50
 12  \w     28.00  88.00   1.00    1.00    --    0.00  38.00  90.00   60
 13  \w     67.00  92.00   1.00    1.00    --   95.80  72.00 119.74   25
 14  \w     73.00 185.00   1.00    1.00    --   95.80  54.00 112.87  112
 15  \w     74.00 184.00   1.00    1.00    --   95.80  49.00 135.10  110
 16  \w     64.00  91.00   1.00    1.00    --   95.80  80.00-166.04   27
 17  \w    149.00 184.00   1.00    1.00    --   95.80  57.00-166.93   35
 18  \w     67.00 138.00   1.00    1.00    --   95.80  71.00  31.52   71
 19  \w     73.00 107.00   1.00    1.00    --   95.80  55.00  18.22   34
 20  \w     71.00 143.00   1.00    1.00    --   95.80  61.00 -60.00   72
 21  \w     10.00 116.00   1.00    1.00    --   95.80 -82.00 -30.00  106
 22  \w     72.00 133.00   1.00    1.00    --   95.80  57.00-166.93   61
 23  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 24  \w     92.00 118.00   1.00    1.00    --   95.80  82.00  60.00   26
 25  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 26  \w    111.00 137.00   1.00    1.00    --   95.80  77.00 -60.00   26
 27  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 28  \w     71.00 183.00   1.00    1.00    --   95.80  61.00  30.00  112
 29  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00  30.00  122
 30  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 150.00   25
 31  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00-180.00  121
 32  \w      7.00 105.00   1.00    1.00    --   95.80 -61.00  30.00   98
 33  \w     67.00  93.00   1.00    1.00    --   95.80  73.00 -32.06   26
 34  \w     69.00  99.00   1.00    1.00    --   95.80  67.00-114.51   30
 35  \w    129.00 155.00   1.00    1.00    --   95.80  82.00-120.00   26
 36  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 37  \w     64.00  89.00   1.00    1.00    --   95.80  79.00 127.69   25
 38  \w    105.00 130.00   1.00    1.00    --   95.80  77.00  90.00   25
 39  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 41  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 42  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 44  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 45  \w     68.00 174.00   1.00    1.00    --   95.80  68.00 -31.39  106
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 47  \w     72.00  98.00   1.00    1.00    --   95.80  61.00  90.00   26
 48  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 49  \w     67.00  93.00   1.00    1.00    --   95.80  73.00 144.44   26
 50  \w     69.00  99.00   1.00    1.00    --   95.80  67.00 -89.06   30
 51  \w    128.00 181.00   1.00    1.00    --   95.80  67.00 -89.06   53
 52  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 53  \w     66.00  91.00   1.00    1.00    --   95.80  77.00  60.00   25
 54  \w     13.00 120.00   1.00    1.00    --   95.80 -61.00-180.00  107
 55  \w    119.00 145.00   1.00    1.00    --   95.80  54.00-122.34   26
 56  \w     85.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   41
 57  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 58  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 59  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 60  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 61  \w     64.00 175.00   1.00    1.00    --   95.80  80.00  48.59  111
 62  \w     71.00  96.00   1.00    1.00    --   95.80  61.00   0.00   25
 63  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-150.00   26
 64  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 65  \w    160.00 185.00   1.00    1.00    --   95.80  72.00 119.74   25
 66  \w     73.00  99.00   1.00    1.00    --   95.80  54.00-122.34   26
 67  \w    120.00 153.00   1.00    1.00    --   95.80  55.00  18.22   33
 68  \w     67.00 185.00   1.00    1.00    --   95.80  71.00-113.20  118
 69  \w     80.00 110.00   1.00    1.00    --   95.80 -82.00  90.00   30
 70  \w     75.00 170.00   1.00    1.00    --   95.80  45.00-122.38   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0457844000
_diffrn_orient_matrix_UB_12      0.0398853000
_diffrn_orient_matrix_UB_13      0.0620241000
_diffrn_orient_matrix_UB_21      0.0095817000
_diffrn_orient_matrix_UB_22      -0.1115410000
_diffrn_orient_matrix_UB_23      0.0256663000
_diffrn_orient_matrix_UB_31      0.1386646000
_diffrn_orient_matrix_UB_32      0.0208988000
_diffrn_orient_matrix_UB_33      0.0187510000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            78117
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.602
_diffrn_reflns_theta_min         4.001
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (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    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.0018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5992
_reflns_number_total             6064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08577_si_002.cif
_cod_data_source_block           exp_778
_cod_database_code               4127665
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.93
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C22(H22), C4(H4), C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C24(H24A,H24B), C10(H10A,H10B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C13(H13A,H13B,
 H13C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              52653
_shelx_hkl_checksum              57777
_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 2.523
_oxdiff_exptl_absorpt_empirical_full_min 0.509