Antiviral spirooliganones A and B with unprecedented skeletons from the roots of Illicium oligandrum.
Ma, Shuang-Gang; Gao, Rong-Mei; Li, Yu-Huan; Jiang, Jian-Dong; Gong, Ning-Bo; Li, Li; Lü, Yang; Tang, Wen-Zhao; Liu, Yun-Bao; Qu, Jing; Lü, Hai-Ning; Li, Yong; Yu, Shi-Shan; Organic letters 15 (2013) 4450–4453; doi:10.1021/ol401992s

data_1556221
_publ_section_title
;
 Antiviral spirooliganones A and B with unprecedented skeletons from the
 roots of Illicium oligandrum.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4450
_journal_page_last               4453
_journal_paper_doi               10.1021/ol401992s
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H37 Br O5'
_chemical_formula_sum            'C32 H37 Br O5'
_chemical_formula_weight         581.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-23
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.307(12)
_cell_angle_beta                 91.544(12)
_cell_angle_gamma                99.152(11)
_cell_formula_units_Z            1
_cell_length_a                   5.9898(8)
_cell_length_b                   9.7098(13)
_cell_length_c                   12.2465(18)
_cell_measurement_reflns_used    6689
_cell_measurement_temperature    104.0
_cell_measurement_theta_max      71.7195
_cell_measurement_theta_min      3.6066
_cell_volume                     702.90(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      104.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  -24.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  120.0000 52

  2 omega  -68.00  -38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  120.0000 30

  3 omega  -37.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  130.0000   83.0000 25

  4 omega   -2.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   96.0000   45.0000 25

  5 omega -100.00  -66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -60.0000 34

  6 omega  -46.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -60.0000 31

  7 omega  -89.00    2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -150.0000 91

  8 omega -112.00  -75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -150.0000 37

  9 omega -113.00  -87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  150.0000 26

 10 omega  -37.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -150.0000 25

 11 omega  -39.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000    0.0000 25

 12 omega  -53.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000 -120.0000 74

 13 omega  -39.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  150.0000 25

 14 omega   11.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   86.0000   82.0000 25

 15 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  126.0000 25

 16 omega   26.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000   60.0000 74

 17 omega   21.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000   12.0000 25

 18 omega   20.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   84.0000  -64.0000 25

 19 omega   21.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000 -115.0000 26

 20 omega  -14.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -30.0000 95

 21 omega   -7.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000   90.0000 85

 22 omega   31.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -151.0000 95

 23 omega   30.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -62.0000 59

 24 omega   33.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   72.0000  118.0000 36

 25 omega   28.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000    1.0000 70

 26 omega   39.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   66.0000  164.0000 49

 27 omega   92.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -62.0000 36

 28 omega   59.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -88.0000   59.0000 30

 29 omega   83.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 95

 30 omega   82.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 63

 31 omega  124.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 47

 32 omega   43.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -127.0000  174.0000 70

 33 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 25

 34 omega   57.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -102.0000  -24.0000 54

 35 omega   89.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 84

 36 omega   82.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 91

 37 omega  126.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 46

 38 omega   82.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 96

 39 omega   82.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 92

 40 omega   82.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 91

 41 omega  149.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 27

 42 omega   82.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 63

 43 omega   82.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 93

 44 omega  152.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26

 45 omega   52.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -88.0000 -175.0000 61

 46 omega   91.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 32

 47 omega   82.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26

 48 omega   83.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0021273000
_diffrn_orient_matrix_UB_12      0.1449370000
_diffrn_orient_matrix_UB_13      0.0521280000
_diffrn_orient_matrix_UB_21      -0.1181872000
_diffrn_orient_matrix_UB_22      -0.0689766000
_diffrn_orient_matrix_UB_23      0.1006147000
_diffrn_orient_matrix_UB_31      0.2323477000
_diffrn_orient_matrix_UB_32      -0.0075827000
_diffrn_orient_matrix_UB_33      0.0546579000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8011
_diffrn_reflns_theta_full        71.91
_diffrn_reflns_theta_max         71.91
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.023(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.1794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                4697
_reflns_number_total             4709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401992s_si_002.cif
_cod_data_source_block           exp_1117
_cod_original_cell_volume        702.89(17)
_cod_database_code               1556221
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97