 
data_PR-XI-25-A1
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H12 O3' 
_chemical_formula_weight          216.23 
 
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            orthorhombic 
_symmetry_space_group_name_H-M    Pbca
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 '-x-1/2, y-1/2, z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    8.1348(4) 
_cell_length_b                    12.0317(5) 
_cell_length_c                    20.4322(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1999.81(16) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     5800
_cell_measurement_theta_min       3.2
_cell_measurement_theta_max       27.1
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.40 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.436 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              912 
_exptl_absorpt_coefficient_mu     0.102 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.80 
_exptl_absorpt_correction_T_max   1.00
_exptl_absorpt_process_details    
;
 Data were corrected for decay and absorption using the program SADABS 
 based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       173(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 CCD area detector' 
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0.0
_diffrn_reflns_number             11475 
_diffrn_reflns_av_R_equivalents   0.0274 
_diffrn_reflns_av_sigmaI/netI     0.0163 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -26 
_diffrn_reflns_limit_l_max        26 
_diffrn_reflns_theta_min          1.99 
_diffrn_reflns_theta_max          27.11 
_reflns_number_total              2213 
_reflns_number_gt                 1851 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'SMART (Bruker, 1998)'
_computing_cell_refinement        'SMART (Bruker, 1998)' 
_computing_data_reduction         'SAINT (Bruker, 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-III (Burnett & Johnson, 1996)' 
_computing_publication_material   'CIFTAB (Sheldrick, 1997)'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0619P)²+0.6060P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2213 
_refine_ls_number_parameters      145 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0472 
_refine_ls_R_factor_gt            0.0398 
_refine_ls_wR_factor_ref          0.1118 
_refine_ls_wR_factor_gt           0.1058 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.052 
_refine_ls_shift/su_max           0.000 
_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 0.16660(13) 0.13360(8) 0.24996(5) 0.0315(3) Uani 1 1 d . . . 
O2 O 0.03801(14) 0.29776(8) 0.24203(5) 0.0352(3) Uani 1 1 d . . . 
O3 O 0.06686(17) 0.34685(10) -0.01732(6) 0.0536(4) Uani 1 1 d . . . 
C1 C 0.06343(16) 0.20697(10) 0.21988(6) 0.0255(3) Uani 1 1 d . . . 
C2 C 0.00401(15) 0.15352(10) 0.15776(6) 0.0210(3) Uani 1 1 d . . . 
C3 C 0.00933(16) 0.02875(10) 0.17308(6) 0.0236(3) Uani 1 1 d . . . 
H3 H -0.0885 -0.0021 0.1965 0.028 Uiso 1 1 calc R . . 
C4 C 0.17060(17) 0.03014(11) 0.21175(7) 0.0286(3) Uani 1 1 d . . . 
H4 H 0.1810 -0.0366 0.2406 0.034 Uiso 1 1 calc R . . 
C5 C 0.30389(17) 0.03134(12) 0.15803(7) 0.0328(3) Uani 1 1 d . . . 
H5A H 0.3659 -0.0394 0.1573 0.039 Uiso 1 1 calc R . . 
H5B H 0.3817 0.0936 0.1646 0.039 Uiso 1 1 calc R . . 
C6 C 0.20348(16) 0.04677(11) 0.09430(7) 0.0282(3) Uani 1 1 d . . . 
H6 H 0.2639 0.0298 0.0529 0.034 Uiso 1 1 calc R . . 
C7 C 0.12908(16) 0.16333(10) 0.09846(6) 0.0238(3) Uani 1 1 d . . . 
H7 H 0.2122 0.2239 0.1037 0.029 Uiso 1 1 calc R . . 
C8 C 0.05481(17) -0.02826(11) 0.10865(7) 0.0283(3) Uani 1 1 d . . . 
H8A H -0.0325 -0.0217 0.0751 0.034 Uiso 1 1 calc R . . 
H8B H 0.0859 -0.1072 0.1146 0.034 Uiso 1 1 calc R . . 
C9 C -0.13565(16) 0.19816(10) 0.11403(6) 0.0232(3) Uani 1 1 d . . . 
H9 H -0.2330 0.1478 0.1107 0.028 Uiso 1 1 calc R . . 
C10 C -0.17780(17) 0.31870(11) 0.12096(6) 0.0274(3) Uani 1 1 d . . . 
H10 H -0.2440 0.3473 0.1554 0.033 Uiso 1 1 calc R . . 
C11 C -0.11303(18) 0.38199(11) 0.07390(7) 0.0306(3) Uani 1 1 d . . . 
H11 H -0.1293 0.4599 0.0698 0.037 Uiso 1 1 calc R . . 
C12 C -0.01285(18) 0.31412(12) 0.02921(7) 0.0317(3) Uani 1 1 d . . . 
C13 C -0.02003(16) 0.19531(11) 0.05369(6) 0.0255(3) Uani 1 1 d . . . 
H13 H -0.0493 0.1388 0.0198 0.031 Uiso 1 1 calc R . . 
 
 
_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 1.3643(16) . ? 
O1 C4 1.4696(16) . ? 
O2 C1 1.2004(16) . ? 
O3 C12 1.2163(18) . ? 
C1 C2 1.5027(17) . ? 
C2 C3 1.5341(17) . ? 
C2 C9 1.5419(17) . ? 
C2 C7 1.5866(17) . ? 
C3 C8 1.5298(18) . ? 
C3 C4 1.5316(18) . ? 
C4 C5 1.543(2) . ? 
C5 C6 1.5482(19) . ? 
C6 C7 1.5299(17) . ? 
C6 C8 1.5373(19) . ? 
C7 C13 1.5671(18) . ? 
C9 C10 1.4969(18) . ? 
C9 C13 1.5511(17) . ? 
C10 C11 1.335(2) . ? 
C11 C12 1.471(2) . ? 
C12 C13 1.5156(18) . ? 
 
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 C4 108.81(9) . . ? 
O2 C1 O1 121.67(12) . . ? 
O2 C1 C2 130.72(12) . . ? 
O1 C1 C2 107.55(10) . . ? 
C1 C2 C3 103.73(10) . . ? 
C1 C2 C9 125.27(11) . . ? 
C3 C2 C9 118.67(10) . . ? 
C1 C2 C7 114.02(10) . . ? 
C3 C2 C7 102.15(9) . . ? 
C9 C2 C7 90.23(9) . . ? 
C8 C3 C4 103.99(11) . . ? 
C8 C3 C2 105.67(10) . . ? 
C4 C3 C2 96.82(10) . . ? 
O1 C4 C3 105.33(10) . . ? 
O1 C4 C5 112.68(11) . . ? 
C3 C4 C5 103.59(11) . . ? 
C4 C5 C6 103.22(11) . . ? 
C7 C6 C8 102.50(10) . . ? 
C7 C6 C5 105.78(11) . . ? 
C8 C6 C5 100.62(10) . . ? 
C6 C7 C13 119.92(11) . . ? 
C6 C7 C2 103.17(9) . . ? 
C13 C7 C2 88.15(9) . . ? 
C3 C8 C6 95.23(10) . . ? 
C10 C9 C2 116.84(10) . . ? 
C10 C9 C13 103.62(10) . . ? 
C2 C9 C13 90.35(9) . . ? 
C11 C10 C9 113.21(12) . . ? 
C10 C11 C12 110.43(12) . . ? 
O3 C12 C11 126.92(14) . . ? 
O3 C12 C13 125.72(13) . . ? 
C11 C12 C13 107.30(11) . . ? 
C12 C13 C9 105.35(10) . . ? 
C12 C13 C7 113.22(11) . . ? 
C9 C13 C7 90.62(9) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C4 O1 C1 O2 179.32(13) . . . . ? 
C4 O1 C1 C2 -3.22(14) . . . . ? 
O2 C1 C2 C3 -154.35(15) . . . . ? 
O1 C1 C2 C3 28.50(13) . . . . ? 
O2 C1 C2 C9 -13.3(2) . . . . ? 
O1 C1 C2 C9 169.56(11) . . . . ? 
O2 C1 C2 C7 95.40(17) . . . . ? 
O1 C1 C2 C7 -81.75(12) . . . . ? 
C1 C2 C3 C8 -146.15(11) . . . . ? 
C9 C2 C3 C8 69.65(14) . . . . ? 
C7 C2 C3 C8 -27.39(12) . . . . ? 
C1 C2 C3 C4 -39.51(12) . . . . ? 
C9 C2 C3 C4 176.29(11) . . . . ? 
C7 C2 C3 C4 79.25(11) . . . . ? 
C1 O1 C4 C3 -23.46(14) . . . . ? 
C1 O1 C4 C5 88.79(13) . . . . ? 
C8 C3 C4 O1 146.27(10) . . . . ? 
C2 C3 C4 O1 38.21(12) . . . . ? 
C8 C3 C4 C5 27.75(12) . . . . ? 
C2 C3 C4 C5 -80.31(11) . . . . ? 
O1 C4 C5 C6 -105.85(12) . . . . ? 
C3 C4 C5 C6 7.46(12) . . . . ? 
C4 C5 C6 C7 66.66(12) . . . . ? 
C4 C5 C6 C8 -39.71(12) . . . . ? 
C8 C6 C7 C13 -56.95(14) . . . . ? 
C5 C6 C7 C13 -161.95(11) . . . . ? 
C8 C6 C7 C2 38.58(12) . . . . ? 
C5 C6 C7 C2 -66.42(12) . . . . ? 
C1 C2 C7 C6 104.26(12) . . . . ? 
C3 C2 C7 C6 -6.94(12) . . . . ? 
C9 C2 C7 C6 -126.40(10) . . . . ? 
C1 C2 C7 C13 -135.40(11) . . . . ? 
C3 C2 C7 C13 113.39(10) . . . . ? 
C9 C2 C7 C13 -6.06(9) . . . . ? 
C4 C3 C8 C6 -51.32(11) . . . . ? 
C2 C3 C8 C6 50.03(12) . . . . ? 
C7 C6 C8 C3 -53.80(12) . . . . ? 
C5 C6 C8 C3 55.16(11) . . . . ? 
C1 C2 C9 C10 20.72(18) . . . . ? 
C3 C2 C9 C10 156.62(11) . . . . ? 
C7 C2 C9 C10 -99.36(12) . . . . ? 
C1 C2 C9 C13 126.21(12) . . . . ? 
C3 C2 C9 C13 -97.89(12) . . . . ? 
C7 C2 C9 C13 6.12(9) . . . . ? 
C2 C9 C10 C11 100.35(14) . . . . ? 
C13 C9 C10 C11 2.90(15) . . . . ? 
C9 C10 C11 C12 -1.80(17) . . . . ? 
C10 C11 C12 O3 -177.44(16) . . . . ? 
C10 C11 C12 C13 -0.14(16) . . . . ? 
O3 C12 C13 C9 179.21(15) . . . . ? 
C11 C12 C13 C9 1.88(14) . . . . ? 
O3 C12 C13 C7 81.74(18) . . . . ? 
C11 C12 C13 C7 -95.59(13) . . . . ? 
C10 C9 C13 C12 -2.74(13) . . . . ? 
C2 C9 C13 C12 -120.52(11) . . . . ? 
C10 C9 C13 C7 111.58(10) . . . . ? 
C2 C9 C13 C7 -6.20(9) . . . . ? 
C6 C7 C13 C12 -142.80(12) . . . . ? 
C2 C7 C13 C12 113.05(11) . . . . ? 
C6 C7 C13 C9 110.17(12) . . . . ? 
C2 C7 C13 C9 6.03(9) . . . . ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              27.11 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.320 
_refine_diff_density_min   -0.185 
_refine_diff_density_rms    0.045 

