data_060723b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 O10 Pr' _chemical_formula_weight 404.05 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' 'Pr' 'Pr' -0.2180 2.8214 '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 21.507(2) _cell_length_b 6.8401(8) _cell_length_c 16.2843(19) _cell_angle_alpha 90.00 _cell_angle_beta 120.453(2) _cell_angle_gamma 90.00 _cell_volume 2065.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4041 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 26.37 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 4.773 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.706349 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5603 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2109 _reflns_number_gt 1977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0087P)^2^+20.7609P] 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 Mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2109 _refine_ls_number_parameters 189 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_restrained_S_all 1.346 _refine_ls_shift/su_max 0.002 _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 Pr1 Pr 0.096221(14) 0.46810(4) 0.151568(18) 0.01357(10) Uani 1 1 d . . . O1 O 0.17769(18) 0.7109(5) 0.2591(3) 0.0187(8) Uani 1 1 d . . . O2 O 0.2761(2) 0.8580(6) 0.2779(3) 0.0257(9) Uani 1 1 d . . . O4 O 0.48795(19) 0.8141(6) 0.5095(3) 0.0211(8) Uani 1 1 d . . . O5 O 0.5240(2) 0.7075(6) 0.6544(3) 0.0252(8) Uani 1 1 d . . . O6 O 0.2824(2) 0.4123(6) 0.5936(3) 0.0273(9) Uani 1 1 d D . . H6 H 0.2389 0.3947 0.5598 0.041 Uiso 1 1 calc R . . O7 O -0.02552(19) 0.3878(6) 0.1312(2) 0.0217(8) Uani 1 1 d . . . O8 O -0.09260(19) 0.4428(7) 0.1973(3) 0.0274(9) Uani 1 1 d . . . O9 O 0.1372(2) 0.6410(7) 0.0525(3) 0.0273(9) Uani 1 1 d D . . O10 O 0.1116(2) 0.1207(6) 0.2093(3) 0.0339(10) Uani 1 1 d D . . C1 C 0.2436(3) 0.7477(7) 0.3041(4) 0.0156(10) Uani 1 1 d . . . C2 C 0.2869(3) 0.6590(7) 0.4025(4) 0.0163(10) Uani 1 1 d . . . O3 O 0.3574(2) 0.7044(6) 0.4433(3) 0.0228(8) Uani 1 1 d . . . C6 C 0.4023(3) 0.6518(7) 0.5349(4) 0.0168(10) Uani 1 1 d . . . C7 C 0.4774(3) 0.7253(7) 0.5692(4) 0.0175(10) Uani 1 1 d . . . C5 C 0.3809(3) 0.5545(8) 0.5877(4) 0.0201(11) Uani 1 1 d . . . H5 H 0.4137 0.5219 0.6507 0.024 Uiso 1 1 calc R . . C4 C 0.3067(3) 0.5020(6) 0.5447(4) 0.0183(11) Uani 1 1 d DU . . C3 C 0.2601(3) 0.5576(8) 0.4484(4) 0.0185(10) Uani 1 1 d . . . H3 H 0.2115 0.5242 0.4173 0.022 Uiso 1 1 calc R . . C8 C -0.0343(3) 0.4157(8) 0.2007(3) 0.0186(11) Uani 1 1 d . . . H9A H 0.108(2) 0.646(11) -0.0071(11) 0.05(2) Uiso 1 1 d D . . H10A H 0.088(3) 0.019(5) 0.182(4) 0.033(19) Uiso 1 1 d D . . H9B H 0.1815(10) 0.626(12) 0.071(4) 0.06(2) Uiso 1 1 d D . . H10B H 0.148(3) 0.107(9) 0.265(3) 0.07(3) Uiso 1 1 d 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 Pr1 0.00926(15) 0.01844(15) 0.01286(14) 0.00064(11) 0.00550(11) -0.00043(11) O1 0.0101(17) 0.0224(19) 0.0200(18) -0.0011(15) 0.0051(15) -0.0023(15) O2 0.0166(19) 0.035(2) 0.024(2) 0.0080(17) 0.0087(16) -0.0033(18) O4 0.0165(19) 0.025(2) 0.0225(19) 0.0057(16) 0.0106(16) -0.0011(16) O5 0.0140(18) 0.033(2) 0.0190(19) 0.0048(17) 0.0012(16) -0.0022(17) O6 0.0178(19) 0.038(2) 0.025(2) 0.0090(18) 0.0099(17) -0.0047(19) O7 0.0143(18) 0.037(2) 0.0155(17) -0.0013(17) 0.0089(15) -0.0024(17) O8 0.0106(17) 0.056(3) 0.0165(18) 0.0045(18) 0.0073(15) 0.0076(19) O9 0.016(2) 0.044(3) 0.020(2) 0.0079(19) 0.0079(17) -0.002(2) O10 0.031(3) 0.032(2) 0.030(2) 0.006(2) 0.009(2) -0.005(2) C1 0.014(2) 0.016(2) 0.017(2) -0.0015(19) 0.007(2) 0.000(2) C2 0.011(2) 0.017(2) 0.018(3) -0.001(2) 0.006(2) 0.001(2) O3 0.0154(18) 0.031(2) 0.0190(19) 0.0031(16) 0.0063(16) -0.0020(17) C6 0.013(2) 0.017(2) 0.016(2) 0.000(2) 0.004(2) -0.001(2) C7 0.013(2) 0.014(2) 0.022(3) 0.002(2) 0.006(2) 0.001(2) C5 0.015(3) 0.023(3) 0.017(2) 0.003(2) 0.004(2) 0.000(2) C4 0.021(3) 0.004(2) 0.029(3) 0.0001(19) 0.012(2) -0.0020(19) C3 0.011(2) 0.022(3) 0.020(2) -0.002(2) 0.006(2) -0.002(2) C8 0.016(3) 0.024(3) 0.013(2) -0.001(2) 0.006(2) -0.004(2) _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 Pr1 O1 2.405(4) . ? Pr1 O9 2.493(4) . ? Pr1 O2 2.495(4) 4_545 ? Pr1 O8 2.508(3) 2 ? Pr1 O10 2.515(4) . ? Pr1 O7 2.527(3) . ? Pr1 O4 2.540(4) 4_545 ? Pr1 O5 2.722(4) 8_465 ? Pr1 O4 2.745(4) 8_465 ? Pr1 O3 2.863(4) 4_545 ? Pr1 C7 3.042(5) 8_465 ? O1 C1 1.248(6) . ? O2 C1 1.242(6) . ? O2 Pr1 2.495(4) 4 ? O4 C7 1.262(6) . ? O4 Pr1 2.540(4) 4 ? O4 Pr1 2.745(4) 8_566 ? O5 C7 1.239(6) . ? O5 Pr1 2.723(4) 8_566 ? O6 C4 1.305(5) . ? O6 H6 0.8200 . ? O7 C8 1.253(6) . ? O8 C8 1.240(6) . ? O8 Pr1 2.508(3) 2 ? O9 H9A 0.849(11) . ? O9 H9B 0.848(11) . ? O10 H10A 0.849(11) . ? O10 H10B 0.849(11) . ? C1 C2 1.513(7) . ? C2 C3 1.345(7) . ? C2 O3 1.348(6) . ? O3 C6 1.351(6) . ? O3 Pr1 2.863(4) 4 ? C6 C5 1.338(7) . ? C6 C7 1.503(7) . ? C7 Pr1 3.042(5) 8_566 ? C5 C4 1.428(7) . ? C5 H5 0.9300 . ? C4 C3 1.419(7) . ? C3 H3 0.9300 . ? C8 C8 1.535(10) 2 ? 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 O1 Pr1 O9 77.14(13) . . ? O1 Pr1 O2 69.37(12) . 4_545 ? O9 Pr1 O2 76.94(13) . 4_545 ? O1 Pr1 O8 72.94(12) . 2 ? O9 Pr1 O8 149.83(14) . 2 ? O2 Pr1 O8 95.82(12) 4_545 2 ? O1 Pr1 O10 118.10(14) . . ? O9 Pr1 O10 131.85(15) . . ? O2 Pr1 O10 68.71(14) 4_545 . ? O8 Pr1 O10 68.39(15) 2 . ? O1 Pr1 O7 124.72(12) . . ? O9 Pr1 O7 134.47(12) . . ? O2 Pr1 O7 145.05(13) 4_545 . ? O8 Pr1 O7 64.42(11) 2 . ? O10 Pr1 O7 77.00(14) . . ? O1 Pr1 O4 155.93(12) . 4_545 ? O9 Pr1 O4 80.18(13) . 4_545 ? O2 Pr1 O4 113.10(11) 4_545 4_545 ? O8 Pr1 O4 128.64(12) 2 4_545 ? O10 Pr1 O4 83.34(14) . 4_545 ? O7 Pr1 O4 68.02(11) . 4_545 ? O1 Pr1 O5 68.66(11) . 8_465 ? O9 Pr1 O5 90.92(13) . 8_465 ? O2 Pr1 O5 137.91(12) 4_545 8_465 ? O8 Pr1 O5 74.79(13) 2 8_465 ? O10 Pr1 O5 137.06(14) . 8_465 ? O7 Pr1 O5 67.51(12) . 8_465 ? O4 Pr1 O5 103.98(11) 4_545 8_465 ? O1 Pr1 O4 103.46(12) . 8_465 ? O9 Pr1 O4 67.93(12) . 8_465 ? O2 Pr1 O4 144.81(12) 4_545 8_465 ? O8 Pr1 O4 115.45(12) 2 8_465 ? O10 Pr1 O4 136.28(13) . 8_465 ? O7 Pr1 O4 68.13(11) . 8_465 ? O4 Pr1 O4 59.90(14) 4_545 8_465 ? O5 Pr1 O4 47.51(11) 8_465 8_465 ? O1 Pr1 O3 120.23(11) . 4_545 ? O9 Pr1 O3 67.41(13) . 4_545 ? O2 Pr1 O3 57.01(11) 4_545 4_545 ? O8 Pr1 O3 132.76(13) 2 4_545 ? O10 Pr1 O3 65.83(13) . 4_545 ? O7 Pr1 O3 114.41(12) . 4_545 ? O4 Pr1 O3 56.11(11) 4_545 4_545 ? O5 Pr1 O3 151.70(11) 8_465 4_545 ? O4 Pr1 O3 105.40(10) 8_465 4_545 ? O1 Pr1 C7 89.09(13) . 8_465 ? O9 Pr1 C7 83.18(14) . 8_465 ? O2 Pr1 C7 153.32(13) 4_545 8_465 ? O8 Pr1 C7 92.47(14) 2 8_465 ? O10 Pr1 C7 137.59(14) . 8_465 ? O7 Pr1 C7 60.59(13) . 8_465 ? O4 Pr1 C7 80.26(13) 4_545 8_465 ? O5 Pr1 C7 24.01(12) 8_465 8_465 ? O4 Pr1 C7 24.50(12) 8_465 8_465 ? O3 Pr1 C7 129.86(12) 4_545 8_465 ? C1 O1 Pr1 139.3(3) . . ? C1 O2 Pr1 134.8(3) . 4 ? C7 O4 Pr1 133.1(3) . 4 ? C7 O4 Pr1 91.1(3) . 8_566 ? Pr1 O4 Pr1 120.10(14) 4 8_566 ? C7 O5 Pr1 92.6(3) . 8_566 ? C4 O6 H6 109.5 . . ? C8 O7 Pr1 118.0(3) . . ? C8 O8 Pr1 120.0(3) . 2 ? Pr1 O9 H9A 117(4) . . ? Pr1 O9 H9B 115(5) . . ? H9A O9 H9B 117(2) . . ? Pr1 O10 H10A 131(4) . . ? Pr1 O10 H10B 112(4) . . ? H10A O10 H10B 117(2) . . ? O2 C1 O1 126.2(5) . . ? O2 C1 C2 117.1(4) . . ? O1 C1 C2 116.6(4) . . ? C3 C2 O3 122.4(5) . . ? C3 C2 C1 126.1(5) . . ? O3 C2 C1 111.4(4) . . ? C2 O3 C6 118.6(4) . . ? C2 O3 Pr1 119.4(3) . 4 ? C6 O3 Pr1 121.0(3) . 4 ? C5 C6 O3 123.8(5) . . ? C5 C6 C7 125.5(5) . . ? O3 C6 C7 110.6(4) . . ? O5 C7 O4 123.4(5) . . ? O5 C7 C6 119.4(5) . . ? O4 C7 C6 117.0(5) . . ? O5 C7 Pr1 63.4(3) . 8_566 ? O4 C7 Pr1 64.4(3) . 8_566 ? C6 C7 Pr1 154.0(3) . 8_566 ? C6 C5 C4 118.2(5) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? O6 C4 C3 121.6(5) . . ? O6 C4 C5 120.9(5) . . ? C3 C4 C5 117.5(4) . . ? C2 C3 C4 119.5(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? O8 C8 O7 126.4(5) . . ? O8 C8 C8 117.5(5) . 2 ? O7 C8 C8 116.1(5) . 2 ? 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 O9 Pr1 O1 C1 -70.1(5) . . . . ? O2 Pr1 O1 C1 10.5(5) 4_545 . . . ? O8 Pr1 O1 C1 113.8(5) 2 . . . ? O10 Pr1 O1 C1 60.7(5) . . . . ? O7 Pr1 O1 C1 154.1(5) . . . . ? O4 Pr1 O1 C1 -90.1(6) 4_545 . . . ? O5 Pr1 O1 C1 -166.3(5) 8_465 . . . ? O4 Pr1 O1 C1 -133.3(5) 8_465 . . . ? O3 Pr1 O1 C1 -16.2(5) 4_545 . . . ? C7 Pr1 O1 C1 -153.4(5) 8_465 . . . ? O1 Pr1 O7 C8 -27.8(4) . . . . ? O9 Pr1 O7 C8 -135.3(4) . . . . ? O2 Pr1 O7 C8 76.3(4) 4_545 . . . ? O8 Pr1 O7 C8 15.5(4) 2 . . . ? O10 Pr1 O7 C8 87.6(4) . . . . ? O4 Pr1 O7 C8 175.5(4) 4_545 . . . ? O5 Pr1 O7 C8 -67.8(4) 8_465 . . . ? O4 Pr1 O7 C8 -119.3(4) 8_465 . . . ? O3 Pr1 O7 C8 143.1(4) 4_545 . . . ? C7 Pr1 O7 C8 -93.4(4) 8_465 . . . ? Pr1 O2 C1 O1 178.7(4) 4 . . . ? Pr1 O2 C1 C2 2.8(7) 4 . . . ? Pr1 O1 C1 O2 95.5(7) . . . . ? Pr1 O1 C1 C2 -88.5(6) . . . . ? O2 C1 C2 C3 170.8(5) . . . . ? O1 C1 C2 C3 -5.5(8) . . . . ? O2 C1 C2 O3 -5.2(6) . . . . ? O1 C1 C2 O3 178.5(4) . . . . ? C3 C2 O3 C6 -2.4(7) . . . . ? C1 C2 O3 C6 173.7(4) . . . . ? C3 C2 O3 Pr1 -170.9(4) . . . 4 ? C1 C2 O3 Pr1 5.2(5) . . . 4 ? C2 O3 C6 C5 0.9(7) . . . . ? Pr1 O3 C6 C5 169.3(4) 4 . . . ? C2 O3 C6 C7 -176.7(4) . . . . ? Pr1 O3 C6 C7 -8.3(5) 4 . . . ? Pr1 O5 C7 O4 24.6(5) 8_566 . . . ? Pr1 O5 C7 C6 -150.6(4) 8_566 . . . ? Pr1 O4 C7 O5 -159.1(4) 4 . . . ? Pr1 O4 C7 O5 -24.3(5) 8_566 . . . ? Pr1 O4 C7 C6 16.2(7) 4 . . . ? Pr1 O4 C7 C6 151.0(4) 8_566 . . . ? Pr1 O4 C7 Pr1 -134.8(4) 4 . . 8_566 ? C5 C6 C7 O5 -4.7(8) . . . . ? O3 C6 C7 O5 172.8(5) . . . . ? C5 C6 C7 O4 179.8(5) . . . . ? O3 C6 C7 O4 -2.6(6) . . . . ? C5 C6 C7 Pr1 -93.6(9) . . . 8_566 ? O3 C6 C7 Pr1 83.9(9) . . . 8_566 ? O3 C6 C5 C4 0.3(8) . . . . ? C7 C6 C5 C4 177.6(5) . . . . ? C6 C5 C4 O6 -177.9(5) . . . . ? C6 C5 C4 C3 -0.2(7) . . . . ? O3 C2 C3 C4 2.6(8) . . . . ? C1 C2 C3 C4 -173.0(5) . . . . ? O6 C4 C3 C2 176.5(5) . . . . ? C5 C4 C3 C2 -1.2(7) . . . . ? Pr1 O8 C8 O7 175.0(4) 2 . . . ? Pr1 O8 C8 C8 -4.9(5) 2 . . 2 ? Pr1 O7 C8 O8 156.4(5) . . . . ? Pr1 O7 C8 C8 -23.6(4) . . . 2 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.439 _refine_diff_density_min -1.272 _refine_diff_density_rms 0.138