A versatile approach to oligostilbenoid natural products – synthesis of permethylated analogues of viniferifuran, malibatol A, and shoreaphenol
Kim, Ikyon; Choi, Jihyun; Organic & Biomolecular Chemistry 7 (2009) 2788–2795; doi:10.1039/b901911a

data_7150654
_publ_section_title
;
 A versatile approach to oligostilbenoid natural products -- synthesis
 of permethylated analogues of viniferifuran, malibatol A, and
 shoreaphenol
;
_journal_issue                   13
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2788
_journal_page_last               2795
_journal_paper_doi               10.1039/b901911a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C38 H34 O12'
_chemical_formula_weight         682.65
_chemical_name_common            3-arylbenzofuran
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.6550(10)
_cell_angle_beta                 81.4100(10)
_cell_angle_gamma                81.7620(10)
_cell_formula_units_Z            1
_cell_length_a                   7.58670(10)
_cell_length_b                   7.95690(10)
_cell_length_c                   14.3677(2)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.62
_cell_volume                     837.59(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15109
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0502P)^2^+0.1037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2750
_reflns_number_total             4103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901911a.txt
_cod_data_source_block           d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        837.591(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150654