Absolute configuration of xerophenone A
Fun, Hoong-Kun; Tantapakul, Cholpisut; Laphookhieo, Surat; Boonnak, Nawong; Chantrapromma, Suchada; Acta Crystallographica Section E 68 (2012) o1451–o1452; doi:10.1107/S1600536812015267

data_2234694
_publ_section_title
;
 Absolute configuration of xerophenone A
;
_journal_coeditor_code           IS5112
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1451
_journal_page_last               o1452
_journal_paper_doi               10.1107/S1600536812015267
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C33 H42 O5'
_chemical_formula_moiety         'C33 H42 O5'
_chemical_formula_sum            'C33 H42 O5'
_chemical_formula_weight         518.67
_chemical_melting_point_gt       451.0
_chemical_melting_point_lt       452.4
_chemical_name_common
;
Xerophenone A
;
_chemical_name_systematic
;
(1<i>R</i>,3<i>R</i>,4<i>R</i>,6<i>S</i>,8<i>E</i>,10<i>R</i>)-10-hydroxy-8-
[hydroxy(phenyl)methylene]-4-methyl-1,6-bis(3-methylbut-2-en-1-yl)-3-(3-
methylbut-3-en-1-yl)-11-oxatricyclo[4.3.1.1^4,10^]undecane-7,9-dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1984(2)
_cell_length_b                   17.0998(4)
_cell_length_c                   13.7007(3)
_cell_measurement_reflns_used    4746
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.47
_cell_measurement_theta_min      3.23
_cell_volume                     1451.92(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX Duo CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11622
_diffrn_reflns_theta_full        67.47
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         3.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_correction_T_min  0.8296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details 'Flack (1983), 2079 Friedel pairs'
_refine_ls_abs_structure_Flack   0.18(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.4822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                4661
_reflns_number_total             4746
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            is5112.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2234694
_cod_database_fobs_code          2234694