Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
Jung, Youngeun; Singh, Dileep Kumar; Kim, Ikyon; Beilstein Journal of Organic Chemistry 12 (2016) 2689–; doi:10.3762/bjoc.12.266

data_4032072
_publ_section_title
;
 Symmetry-based approach to oligostilbenoids: Rapid entry to
 viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2689
_journal_paper_doi               10.3762/bjoc.12.266
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C18 H16 O5'
_chemical_formula_sum            'C18 H16 O5'
_chemical_formula_weight         312.31
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.529(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0577(9)
_cell_length_b                   12.8224(10)
_cell_length_c                   11.7987(10)
_cell_measurement_reflns_used    3688
_cell_measurement_temperature    303.4
_cell_measurement_theta_max      22.04
_cell_measurement_theta_min      2.43
_cell_volume                     1566.7(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      303.4
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21199
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.068
_diffrn_reflns_theta_min         2.433
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0598 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0651
_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^)+(0.0723P)^2^+0.5864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1685
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-266-S2.cif
_cod_data_source_block           benzofuran
_cod_database_code               4032072
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O14-C15A \\sim O14-C15
 with sigma of 0.005
3. Others
 Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C15A(H15A,H15B,H15C), C15(H15D,H15E,
 H15F)
;
_shelx_res_checksum              31216
_shelx_hkl_checksum              99120
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'