data_05198 

  

_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

 ? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

 'C32 H20 O3' 

_chemical_formula_weight          452.48 

  

loop_ 

 _atom_type_symbol 

 _atom_type_description 

 _atom_type_scat_dispersion_real 

 _atom_type_scat_dispersion_imag 

 _atom_type_scat_source 

 'C'  'C'   0.0033   0.0016 

 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

 'H'  'H'   0.0000   0.0000 

 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

 'O'  'O'   0.0106   0.0060 

 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

  

_symmetry_cell_setting            Monoclinic 

_symmetry_space_group_name_H-M    C2/c 

  

loop_ 

 _symmetry_equiv_pos_as_xyz 

 'x, y, z' 

 '-x, y, -z+1/2' 

 'x+1/2, y+1/2, z' 

 '-x+1/2, y+1/2, -z+1/2' 

 '-x, -y, -z' 

 'x, -y, z-1/2' 

 '-x+1/2, -y+1/2, -z' 

 'x+1/2, -y+1/2, z-1/2' 

  

_cell_length_a                    14.767(2) 

_cell_length_b                    9.1855(12) 

_cell_length_c                    16.607(3) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  105.692(6) 

_cell_angle_gamma                 90.00 

_cell_volume                      2168.7(5) 

_cell_formula_units_Z             4 

_cell_measurement_temperature     100(2) 

_cell_measurement_reflns_used     5207 

_cell_measurement_theta_min       2.55 

_cell_measurement_theta_max       30.41 

  

_exptl_crystal_description        plate 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           0.40 

_exptl_crystal_size_mid           0.20 

_exptl_crystal_size_min           0.05 

_exptl_crystal_density_meas       'not measured' 

_exptl_crystal_density_diffrn     1.386 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              944 

_exptl_absorpt_coefficient_mu     0.088 

_exptl_absorpt_correction_type    multi-scan 

_exptl_absorpt_correction_T_min   0.9656 

_exptl_absorpt_correction_T_max   0.9956 

_exptl_absorpt_process_details    sadabs 

  

_exptl_special_details 

; 

 'Siemens three-circle diffractometer, Bruker APEX CCD' 

; 

  

_diffrn_ambient_temperature       100(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Bruker Smart APEX CCD' 

_diffrn_measurement_method        'omega and phi scans' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             23427 

_diffrn_reflns_av_R_equivalents   0.0298 

_diffrn_reflns_av_sigmaI/netI     0.0161 

_diffrn_reflns_limit_h_min        -20 

_diffrn_reflns_limit_h_max        20 

_diffrn_reflns_limit_k_min        -12 

_diffrn_reflns_limit_k_max        12 

_diffrn_reflns_limit_l_min        -23 

_diffrn_reflns_limit_l_max        23 

_diffrn_reflns_theta_min          2.55 

_diffrn_reflns_theta_max          29.57 

_reflns_number_total              3047 

_reflns_number_gt                 2750 

_reflns_threshold_expression      >2sigma(I) 

  

_computing_data_collection        'SMART 5 (Bruker-AXS, 2003)' 

_computing_cell_refinement        'SAINT 5 (Bruker-AXS, 2003)' 

_computing_data_reduction         'SAINT 5 (Bruker-AXS, 2003)' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'Bruker SHELXTL' 

_computing_publication_material   'Bruker SHELXTL' 

  

_refine_special_details 

; 

 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F^2^, conventional R-factors R are based 

 on F, with F set to zero for negative F^2^. The threshold expression of 

 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F^2^ are statistically about twice as large as those based on F, and R- 

 factors based on ALL data will be even larger. 

; 

  

_refine_ls_structure_factor_coef  Fsqd 

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc 

_refine_ls_weighting_details 

 'calc w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+1.6450P] where P=(Fo^2^+2Fc^2^)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     constr 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          3047 

_refine_ls_number_parameters      159 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0471 

_refine_ls_R_factor_gt            0.0427 

_refine_ls_wR_factor_ref          0.1187 

_refine_ls_wR_factor_gt           0.1130 

_refine_ls_goodness_of_fit_ref    1.051 

_refine_ls_restrained_S_all       1.051 

_refine_ls_shift/su_max           0.001 

_refine_ls_shift/su_mean          0.000 

  

loop_ 

 _atom_site_label 

 _atom_site_type_symbol 

 _atom_site_fract_x 

 _atom_site_fract_y 

 _atom_site_fract_z 

 _atom_site_U_iso_or_equiv 

 _atom_site_adp_type 

 _atom_site_occupancy 

 _atom_site_symmetry_multiplicity 

 _atom_site_calc_flag 

 _atom_site_refinement_flags 

 _atom_site_disorder_assembly 

 _atom_site_disorder_group 

O1 O 0.0000 0.98726(11) 0.2500 0.0160(2) Uani 1 2 d S . . 

O2 O 0.11558(5) 1.01855(8) 0.18710(5) 0.01888(18) Uani 1 1 d . . . 

C1 C 0.05917(7) 1.07296(11) 0.21774(6) 0.0142(2) Uani 1 1 d . . . 

C2 C 0.04011(6) 1.23370(11) 0.22769(6) 0.01222(19) Uani 1 1 d . . . 

C3 C 0.13115(7) 1.30257(10) 0.28698(6) 0.01280(19) Uani 1 1 d . . . 

H3 H 0.1843 1.3057 0.2604 0.015 Uiso 1 1 calc R . . 

C4 C 0.10814(7) 1.45178(11) 0.31480(6) 0.01352(19) Uani 1 1 d . . . 

C5 C 0.15508(7) 1.57971(11) 0.30748(6) 0.0162(2) Uani 1 1 d . . . 

H5 H 0.2038 1.5800 0.2801 0.019 Uiso 1 1 calc R . . 

C6 C 0.12984(8) 1.70804(12) 0.34090(7) 0.0201(2) Uani 1 1 d . . . 

H6 H 0.1615 1.7963 0.3362 0.024 Uiso 1 1 calc R . . 

C7 C 0.05832(8) 1.70719(12) 0.38116(7) 0.0207(2) Uani 1 1 d . . . 

H7 H 0.0414 1.7952 0.4035 0.025 Uiso 1 1 calc R . . 

C8 C 0.01138(7) 1.57844(11) 0.38898(6) 0.0171(2) Uani 1 1 d . . . 

H8 H -0.0370 1.5780 0.4168 0.020 Uiso 1 1 calc R . . 

C9 C 0.03637(7) 1.45084(11) 0.35555(6) 0.0138(2) Uani 1 1 d . . . 

C10 C -0.00275(7) 1.30043(11) 0.36234(6) 0.01328(19) Uani 1 1 d . . . 

H10 H -0.0521 1.3013 0.3934 0.016 Uiso 1 1 calc R . . 

C11 C 0.08134(7) 1.20629(11) 0.40552(6) 0.0140(2) Uani 1 1 d . . . 

C12 C 0.08994(7) 1.12166(11) 0.47663(6) 0.0166(2) Uani 1 1 d . . . 

H12 H 0.0410 1.1202 0.5038 0.020 Uiso 1 1 calc R . . 

C13 C 0.17123(8) 1.03877(12) 0.50773(7) 0.0192(2) Uani 1 1 d . . . 

H13 H 0.1775 0.9806 0.5562 0.023 Uiso 1 1 calc R . . 

C14 C 0.24312(8) 1.04098(12) 0.46799(7) 0.0188(2) Uani 1 1 d . . . 

H14 H 0.2983 0.9846 0.4897 0.023 Uiso 1 1 calc R . . 

C15 C 0.23453(7) 1.12580(11) 0.39622(6) 0.0162(2) Uani 1 1 d . . . 

H15 H 0.2835 1.1272 0.3691 0.019 Uiso 1 1 calc R . . 

C16 C 0.15363(7) 1.20787(10) 0.36521(6) 0.01382(19) Uani 1 1 d . . . 

  

loop_ 

 _atom_site_aniso_label 

 _atom_site_aniso_U_11 

 _atom_site_aniso_U_22 

 _atom_site_aniso_U_33 

 _atom_site_aniso_U_23 

 _atom_site_aniso_U_13 

 _atom_site_aniso_U_12 

O1 0.0159(5) 0.0136(5) 0.0197(5) 0.000 0.0067(4) 0.000 

O2 0.0174(4) 0.0192(4) 0.0215(4) -0.0025(3) 0.0077(3) 0.0025(3) 

C1 0.0130(4) 0.0151(4) 0.0139(4) -0.0004(3) 0.0023(3) 0.0001(3) 

C2 0.0113(4) 0.0127(4) 0.0129(4) 0.0001(3) 0.0037(3) 0.0002(3) 

C3 0.0107(4) 0.0144(4) 0.0137(4) -0.0005(3) 0.0040(3) -0.0002(3) 

C4 0.0125(4) 0.0142(4) 0.0130(4) -0.0002(3) 0.0018(3) 0.0000(3) 

C5 0.0147(4) 0.0171(5) 0.0157(4) 0.0015(3) 0.0022(4) -0.0011(3) 

C6 0.0220(5) 0.0147(5) 0.0216(5) 0.0005(4) 0.0025(4) -0.0022(4) 

C7 0.0235(5) 0.0159(5) 0.0213(5) -0.0028(4) 0.0039(4) 0.0027(4) 

C8 0.0158(4) 0.0187(5) 0.0161(4) -0.0020(4) 0.0032(4) 0.0027(4) 

C9 0.0125(4) 0.0149(4) 0.0133(4) -0.0004(3) 0.0022(3) 0.0001(3) 

C10 0.0121(4) 0.0154(4) 0.0128(4) -0.0004(3) 0.0042(3) -0.0004(3) 

C11 0.0134(4) 0.0144(4) 0.0133(4) -0.0008(3) 0.0022(3) -0.0009(3) 

C12 0.0177(5) 0.0175(5) 0.0140(4) -0.0003(3) 0.0037(4) -0.0030(4) 

C13 0.0226(5) 0.0175(5) 0.0148(4) 0.0020(4) 0.0004(4) -0.0015(4) 

C14 0.0175(5) 0.0180(5) 0.0177(5) -0.0001(4) -0.0009(4) 0.0020(4) 

C15 0.0137(4) 0.0171(4) 0.0167(5) -0.0020(4) 0.0019(4) 0.0006(4) 

C16 0.0138(4) 0.0136(4) 0.0134(4) -0.0007(3) 0.0024(3) -0.0008(3) 

  

_geom_special_details 

; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

; 

  

loop_ 

 _geom_bond_atom_site_label_1 

 _geom_bond_atom_site_label_2 

 _geom_bond_distance 

 _geom_bond_site_symmetry_2 

 _geom_bond_publ_flag 

O1 C1 1.3868(11) . ? 

O1 C1 1.3869(11) 2 ? 

O2 C1 1.1967(12) . ? 

C1 C2 1.5204(14) . ? 

C2 C2 1.5580(18) 2 ? 

C2 C3 1.5688(13) . ? 

C2 C10 1.5714(13) 2 ? 

C3 C4 1.5141(13) . ? 

C3 C16 1.5237(14) . ? 

C4 C5 1.3862(14) . ? 

C4 C9 1.4032(14) . ? 

C5 C6 1.3959(15) . ? 

C6 C7 1.3943(16) . ? 

C7 C8 1.3946(15) . ? 

C8 C9 1.3889(14) . ? 

C9 C10 1.5135(13) . ? 

C10 C11 1.5238(14) . ? 

C10 C2 1.5714(13) 2 ? 

C11 C12 1.3907(14) . ? 

C11 C16 1.4051(14) . ? 

C12 C13 1.3972(15) . ? 

C13 C14 1.3935(16) . ? 

C14 C15 1.4007(15) . ? 

C15 C16 1.3885(14) . ? 

  

loop_ 

 _geom_angle_atom_site_label_1 

 _geom_angle_atom_site_label_2 

 _geom_angle_atom_site_label_3 

 _geom_angle 

 _geom_angle_site_symmetry_1 

 _geom_angle_site_symmetry_3 

 _geom_angle_publ_flag 

C1 O1 C1 110.83(11) . 2 ? 

O2 C1 O1 120.73(9) . . ? 

O2 C1 C2 128.49(9) . . ? 

O1 C1 C2 110.78(8) . . ? 

C1 C2 C2 103.80(5) . 2 ? 

C1 C2 C3 107.90(8) . . ? 

C2 C2 C3 109.53(9) 2 . ? 

C1 C2 C10 107.64(8) . 2 ? 

C2 C2 C10 109.64(9) 2 2 ? 

C3 C2 C10 117.43(8) . 2 ? 

C4 C3 C16 105.76(8) . . ? 

C4 C3 C2 109.37(8) . . ? 

C16 C3 C2 104.89(8) . . ? 

C5 C4 C9 120.55(9) . . ? 

C5 C4 C3 125.57(9) . . ? 

C9 C4 C3 113.75(8) . . ? 

C4 C5 C6 119.16(10) . . ? 

C7 C6 C5 120.28(10) . . ? 

C6 C7 C8 120.63(10) . . ? 

C9 C8 C7 119.07(10) . . ? 

C8 C9 C4 120.30(9) . . ? 

C8 C9 C10 126.34(9) . . ? 

C4 C9 C10 113.26(8) . . ? 

C9 C10 C11 105.91(8) . . ? 

C9 C10 C2 109.15(8) . 2 ? 

C11 C10 C2 104.96(8) . 2 ? 

C12 C11 C16 120.24(9) . . ? 

C12 C11 C10 126.33(9) . . ? 

C16 C11 C10 113.41(8) . . ? 

C11 C12 C13 119.38(10) . . ? 

C14 C13 C12 120.36(10) . . ? 

C13 C14 C15 120.38(10) . . ? 

C16 C15 C14 119.24(9) . . ? 

C15 C16 C11 120.40(9) . . ? 

C15 C16 C3 126.40(9) . . ? 

C11 C16 C3 113.19(8) . . ? 

  

_diffrn_measured_fraction_theta_max    1.000 

_diffrn_reflns_theta_full              29.57 

_diffrn_measured_fraction_theta_full   1.000 

_refine_diff_density_max    0.475 

_refine_diff_density_min   -0.249 

_refine_diff_density_rms    0.058