# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Sun, Zhen-Gang' _publ_contact_author_email szg188@163.com loop_ _publ_author_name Y.Zhu Z.-G.Sun F.Tong Z.Liu C.Huang W.Wang C.-Q.Jiao ; C.-L.Wang ; C.Li K.Chen data_szg92 _database_code_depnum_ccdc_archive 'CCDC 705728' #TrackingRef '- szg92(705728).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 La N O12 P2' _chemical_formula_weight 557.11 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 '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 28.085(9) _cell_length_b 9.131(3) _cell_length_c 17.632(6) _cell_angle_alpha 90.00 _cell_angle_beta 126.854(3) _cell_angle_gamma 90.00 _cell_volume 3618(2) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2837 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 2.602 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6901 _exptl_absorpt_correction_T_max 0.8208 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9765 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.49 _reflns_number_total 3740 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. The final difference Fourier maps showed residual peaks of 2.221 e \%A^-3^ (0.94 \%A from La1 atom) and holes of -1.186 e \%A^-3^(0.95 \%A from La1 atom). The relatively higher residuals are due to the absorption correction problems with the heavy La(III) ions. ; _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^)+(0.0593P)^2^+0.0000P] 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 3740 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 La1 La 0.247288(13) 0.63910(3) 0.61406(2) 0.01993(12) Uani 1 1 d . . . P1 P 0.38075(6) 0.75051(15) 0.63181(10) 0.0232(3) Uani 1 1 d . . . P2 P 0.27096(6) 1.04771(14) 0.56992(10) 0.0217(3) Uani 1 1 d . . . O1 O 0.34648(17) 0.6554(4) 0.6524(3) 0.0292(9) Uani 1 1 d . . . O2 O 0.34710(16) 0.8303(4) 0.5391(3) 0.0267(8) Uani 1 1 d . . . O3 O 0.43382(17) 0.6651(4) 0.6471(3) 0.0348(10) Uani 1 1 d . . . H3A H 0.4334 0.6770 0.5986 0.052 Uiso 1 1 d R . . O4 O 0.25540(18) 0.8924(4) 0.5724(3) 0.0323(9) Uani 1 1 d . . . O5 O 0.26740(18) 1.0876(4) 0.4832(3) 0.0308(9) Uani 1 1 d . . . O6 O 0.23140(18) 1.1538(4) 0.5800(3) 0.0309(9) Uani 1 1 d . . . H6A H 0.2330 1.2383 0.5606 0.046 Uiso 1 1 d R . . O7 O 0.30778(17) 0.7885(4) 0.7664(3) 0.0304(9) Uani 1 1 d . . . O8 O 0.30838(17) 0.9637(4) 0.8549(3) 0.0332(9) Uani 1 1 d . . . O9 O 0.18783(18) 0.7785(5) 0.6604(3) 0.0389(10) Uani 1 1 d . . . O10 O 0.18983(17) 0.9468(4) 0.7545(3) 0.0358(10) Uani 1 1 d . . . O1W O 0.4391(3) 0.6831(7) 0.5070(4) 0.084(2) Uani 1 1 d . . . H1WA H 0.4674 0.6585 0.5048 0.126 Uiso 1 1 d R . . H1WB H 0.4118 0.7247 0.4549 0.126 Uiso 1 1 d R . . O2W O 0.0733(3) 0.1101(7) 0.6033(5) 0.096(2) Uani 1 1 d . . . H2WA H 0.0496 0.0656 0.6105 0.143 Uiso 1 1 d R . . H2WB H 0.0937 0.1726 0.6480 0.143 Uiso 1 1 d R . . N1 N 0.38232(18) 0.9688(5) 0.7465(3) 0.0246(10) Uani 1 1 d . . . H1A H 0.3557 0.9049 0.7417 0.030 Uiso 1 1 d R . . C1 C 0.4207(3) 0.8822(6) 0.7293(4) 0.0286(12) Uani 1 1 d . . . H1B H 0.4409 0.9497 0.7154 0.034 Uiso 1 1 d R . . H1C H 0.4505 0.8299 0.7865 0.034 Uiso 1 1 d R . . C2 C 0.3460(3) 1.0878(6) 0.6751(4) 0.0339(13) Uani 1 1 d . . . H2A H 0.3438 1.1696 0.7077 0.041 Uiso 1 1 d R . . H2B H 0.3677 1.1205 0.6520 0.041 Uiso 1 1 d R . . C3 C 0.4211(3) 1.0301(7) 0.8479(4) 0.0345(14) Uani 1 1 d . . . H3B H 0.3967 1.0857 0.8589 0.041 Uiso 1 1 d R . . H3C H 0.4378 0.9485 0.8916 0.041 Uiso 1 1 d R . . C4 C 0.4710(3) 1.1276(6) 0.8678(4) 0.0321(13) Uani 1 1 d . . . C5 C 0.5284(3) 1.0731(7) 0.9164(4) 0.0350(14) Uani 1 1 d . . . H5 H 0.5359 0.9761 0.9366 0.042 Uiso 1 1 calc R . . C6 C 0.5745(3) 1.1604(8) 0.9353(4) 0.0422(16) Uani 1 1 d . . . H6 H 0.6130 1.1233 0.9695 0.051 Uiso 1 1 calc R . . C7 C 0.5631(3) 1.3032(8) 0.9029(5) 0.0499(18) Uani 1 1 d . . . H7 H 0.5937 1.3617 0.9135 0.060 Uiso 1 1 calc R . . C8 C 0.5057(3) 1.3594(7) 0.8545(5) 0.0445(16) Uani 1 1 d . . . H8 H 0.4979 1.4557 0.8331 0.053 Uiso 1 1 calc R . . C9 C 0.4610(3) 1.2725(7) 0.8384(4) 0.0371(14) Uani 1 1 d . . . H9 H 0.4229 1.3114 0.8071 0.045 Uiso 1 1 calc R . . C10 C 0.2825(2) 0.8729(5) 0.7894(4) 0.0242(11) Uani 1 1 d . . . C11 C 0.2136(3) 0.8648(6) 0.7286(4) 0.0294(13) 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 La1 0.02424(19) 0.01602(17) 0.02465(18) 0.00011(12) 0.01740(15) -0.00042(12) P1 0.0215(7) 0.0242(7) 0.0279(7) -0.0002(6) 0.0169(6) 0.0023(5) P2 0.0253(8) 0.0164(7) 0.0271(7) -0.0007(5) 0.0177(6) -0.0004(5) O1 0.030(2) 0.028(2) 0.038(2) 0.0020(17) 0.0243(19) 0.0009(16) O2 0.026(2) 0.028(2) 0.029(2) -0.0014(16) 0.0181(18) -0.0011(15) O3 0.030(2) 0.045(3) 0.036(2) 0.0066(18) 0.024(2) 0.0144(18) O4 0.033(2) 0.017(2) 0.042(2) 0.0039(17) 0.020(2) -0.0001(16) O5 0.048(3) 0.0212(19) 0.031(2) 0.0017(16) 0.028(2) 0.0043(17) O6 0.040(2) 0.023(2) 0.040(2) 0.0025(17) 0.030(2) 0.0057(16) O7 0.031(2) 0.033(2) 0.034(2) -0.0082(17) 0.0234(19) -0.0002(17) O8 0.027(2) 0.038(2) 0.036(2) -0.0146(18) 0.0189(19) -0.0018(17) O9 0.037(2) 0.041(3) 0.044(2) -0.023(2) 0.027(2) -0.0122(19) O10 0.030(2) 0.039(3) 0.046(2) -0.0166(19) 0.027(2) -0.0031(18) O1W 0.127(6) 0.086(4) 0.095(4) 0.033(4) 0.097(5) 0.040(4) O2W 0.067(4) 0.120(6) 0.085(5) 0.012(4) 0.038(4) -0.028(4) N1 0.020(2) 0.031(3) 0.027(2) -0.0038(19) 0.016(2) -0.0041(18) C1 0.023(3) 0.033(3) 0.031(3) -0.004(2) 0.017(3) -0.001(2) C2 0.028(3) 0.024(3) 0.047(4) -0.006(3) 0.021(3) -0.002(2) C3 0.038(4) 0.041(4) 0.033(3) -0.008(3) 0.026(3) -0.007(3) C4 0.032(3) 0.039(4) 0.030(3) -0.012(2) 0.021(3) -0.008(2) C5 0.033(4) 0.038(4) 0.032(3) -0.008(3) 0.018(3) -0.001(3) C6 0.027(4) 0.059(5) 0.036(3) -0.007(3) 0.017(3) -0.002(3) C7 0.041(4) 0.054(5) 0.063(5) -0.015(4) 0.036(4) -0.017(3) C8 0.043(4) 0.033(4) 0.055(4) -0.004(3) 0.028(4) -0.007(3) C9 0.034(4) 0.035(4) 0.040(4) -0.007(3) 0.021(3) 0.001(3) C10 0.028(3) 0.022(3) 0.032(3) 0.000(2) 0.023(3) 0.001(2) C11 0.033(3) 0.029(3) 0.038(3) -0.004(2) 0.028(3) -0.006(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 La1 O2 2.410(4) 7_566 ? La1 O1 2.445(4) . ? La1 O4 2.478(4) . ? La1 O8 2.517(4) 4_546 ? La1 O7 2.547(4) . ? La1 O5 2.559(4) 7_566 ? La1 O10 2.581(4) 4_546 ? La1 O9 2.591(4) . ? La1 P2 3.4207(16) 7_566 ? P1 O1 1.494(4) . ? P1 O2 1.498(4) . ? P1 O3 1.556(4) . ? P1 C1 1.829(6) . ? P2 O4 1.492(4) . ? P2 O5 1.515(4) . ? P2 O6 1.563(4) . ? P2 C2 1.823(6) . ? P2 La1 3.4207(16) 7_566 ? O2 La1 2.410(4) 7_566 ? O3 H3A 0.8547 . ? O5 La1 2.559(4) 7_566 ? O6 H6A 0.8567 . ? O7 C10 1.268(6) . ? O8 C10 1.242(6) . ? O8 La1 2.517(4) 4_556 ? O9 C11 1.243(6) . ? O10 C11 1.257(6) . ? O10 La1 2.581(4) 4_556 ? O1W H1WA 0.8502 . ? O1W H1WB 0.8549 . ? O2W H2WA 0.8520 . ? O2W H2WB 0.8561 . ? N1 C2 1.506(7) . ? N1 C1 1.508(7) . ? N1 C3 1.535(7) . ? N1 H1A 0.9128 . ? C1 H1B 0.9637 . ? C1 H1C 0.9658 . ? C2 H2A 0.9669 . ? C2 H2B 0.9620 . ? C3 C4 1.512(8) . ? C3 H3B 0.9623 . ? C3 H3C 0.9675 . ? C4 C9 1.387(8) . ? C4 C5 1.388(8) . ? C5 C6 1.382(9) . ? C5 H5 0.9300 . ? C6 C7 1.382(10) . ? C6 H6 0.9300 . ? C7 C8 1.393(10) . ? C7 H7 0.9300 . ? C8 C9 1.363(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.553(8) . ? 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 O2 La1 O1 127.44(13) 7_566 . ? O2 La1 O4 78.15(13) 7_566 . ? O1 La1 O4 74.53(13) . . ? O2 La1 O8 84.73(12) 7_566 4_546 ? O1 La1 O8 137.03(12) . 4_546 ? O4 La1 O8 146.89(13) . 4_546 ? O2 La1 O7 135.15(12) 7_566 . ? O1 La1 O7 75.34(12) . . ? O4 La1 O7 71.98(13) . . ? O8 La1 O7 102.70(13) 4_546 . ? O2 La1 O5 73.50(12) 7_566 7_566 ? O1 La1 O5 86.19(13) . 7_566 ? O4 La1 O5 124.26(12) . 7_566 ? O8 La1 O5 76.11(13) 4_546 7_566 ? O7 La1 O5 151.35(12) . 7_566 ? O2 La1 O10 141.74(13) 7_566 4_546 ? O1 La1 O10 74.96(12) . 4_546 ? O4 La1 O10 139.98(13) . 4_546 ? O8 La1 O10 63.37(12) 4_546 4_546 ? O7 La1 O10 75.71(13) . 4_546 ? O5 La1 O10 78.47(13) 7_566 4_546 ? O2 La1 O9 79.20(13) 7_566 . ? O1 La1 O9 136.52(12) . . ? O4 La1 O9 79.99(13) . . ? O8 La1 O9 69.01(14) 4_546 . ? O7 La1 O9 63.43(12) . . ? O5 La1 O9 137.18(13) 7_566 . ? O10 La1 O9 105.91(14) 4_546 . ? O2 La1 P2 63.70(9) 7_566 7_566 ? O1 La1 P2 77.91(9) . 7_566 ? O4 La1 P2 99.94(10) . 7_566 ? O8 La1 P2 97.46(10) 4_546 7_566 ? O7 La1 P2 153.23(9) . 7_566 ? O5 La1 P2 24.32(8) 7_566 7_566 ? O10 La1 P2 98.33(10) 4_546 7_566 ? O9 La1 P2 141.79(9) . 7_566 ? O1 P1 O2 118.1(2) . . ? O1 P1 O3 110.9(2) . . ? O2 P1 O3 110.2(2) . . ? O1 P1 C1 106.0(2) . . ? O2 P1 C1 109.6(2) . . ? O3 P1 C1 100.5(2) . . ? O4 P2 O5 114.5(2) . . ? O4 P2 O6 110.2(2) . . ? O5 P2 O6 110.2(2) . . ? O4 P2 C2 109.9(3) . . ? O5 P2 C2 108.3(3) . . ? O6 P2 C2 103.1(2) . . ? O4 P2 La1 71.00(16) . 7_566 ? O5 P2 La1 44.07(15) . 7_566 ? O6 P2 La1 134.83(17) . 7_566 ? C2 P2 La1 119.3(2) . 7_566 ? P1 O1 La1 139.6(2) . . ? P1 O2 La1 146.0(2) . 7_566 ? P1 O3 H3A 109.1 . . ? P2 O4 La1 167.5(3) . . ? P2 O5 La1 111.6(2) . 7_566 ? P2 O6 H6A 107.6 . . ? C10 O7 La1 121.0(3) . . ? C10 O8 La1 122.2(3) . 4_556 ? C11 O9 La1 120.4(4) . . ? C11 O10 La1 120.4(4) . 4_556 ? H1WA O1W H1WB 109.3 . . ? H2WA O2W H2WB 109.4 . . ? C2 N1 C1 114.7(4) . . ? C2 N1 C3 111.3(4) . . ? C1 N1 C3 109.4(4) . . ? C2 N1 H1A 106.1 . . ? C1 N1 H1A 107.0 . . ? C3 N1 H1A 108.1 . . ? N1 C1 P1 115.1(4) . . ? N1 C1 H1B 108.5 . . ? P1 C1 H1B 107.7 . . ? N1 C1 H1C 108.9 . . ? P1 C1 H1C 108.4 . . ? H1B C1 H1C 108.0 . . ? N1 C2 P2 119.7(4) . . ? N1 C2 H2A 108.2 . . ? P2 C2 H2A 108.3 . . ? N1 C2 H2B 107.1 . . ? P2 C2 H2B 105.7 . . ? H2A C2 H2B 107.1 . . ? C4 C3 N1 113.4(4) . . ? C4 C3 H3B 108.4 . . ? N1 C3 H3B 109.4 . . ? C4 C3 H3C 109.3 . . ? N1 C3 H3C 108.2 . . ? H3B C3 H3C 108.0 . . ? C9 C4 C5 118.2(6) . . ? C9 C4 C3 121.6(6) . . ? C5 C4 C3 120.2(6) . . ? C6 C5 C4 121.1(6) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.6(6) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 119.8(6) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 119.8(6) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 121.5(6) . . ? C8 C9 H9 119.2 . . ? C4 C9 H9 119.2 . . ? O8 C10 O7 125.1(5) . . ? O8 C10 C11 117.8(5) . . ? O7 C10 C11 117.1(5) . . ? O9 C11 O10 127.0(6) . . ? O9 C11 C10 117.3(5) . . ? O10 C11 C10 115.7(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.221 _refine_diff_density_min -1.186 _refine_diff_density_rms 0.161 # Attachment '- szg93(705729).cif' data_szg93 _database_code_depnum_ccdc_archive 'CCDC 705729' #TrackingRef '- szg93(705729).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Ce N O12 P2' _chemical_formula_weight 558.32 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 '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 28.090(3) _cell_length_b 9.0958(9) _cell_length_c 17.5746(17) _cell_angle_alpha 90.00 _cell_angle_beta 126.8630(10) _cell_angle_gamma 90.00 _cell_volume 3592.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3789 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 2.776 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6407 _exptl_absorpt_correction_T_max 0.7922 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9812 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3716 _reflns_number_gt 3124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0262P)^2^+0.5935P] 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 3716 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0576 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Ce1 Ce 0.247434(8) 0.639230(19) 0.615311(12) 0.01727(6) Uani 1 1 d . . . P1 P 0.37940(4) 0.74999(10) 0.63060(6) 0.02046(19) Uani 1 1 d . . . P2 P 0.27010(4) 1.04713(9) 0.56991(6) 0.01931(19) Uani 1 1 d . . . O1 O 0.34489(11) 0.6550(2) 0.65124(16) 0.0271(5) Uani 1 1 d . . . O2 O 0.34583(10) 0.8302(2) 0.53759(15) 0.0239(5) Uani 1 1 d . . . O3 O 0.43225(11) 0.6626(3) 0.64590(17) 0.0324(6) Uani 1 1 d . . . H3A H 0.4319 0.6745 0.5974 0.049 Uiso 1 1 d R . . O4 O 0.25496(11) 0.8925(2) 0.57506(17) 0.0289(6) Uani 1 1 d . . . O5 O 0.26599(11) 1.0843(3) 0.48227(15) 0.0277(6) Uani 1 1 d . . . O6 O 0.23067(11) 1.1558(2) 0.57975(17) 0.0270(5) Uani 1 1 d . . . H6A H 0.2322 1.2403 0.5603 0.041 Uiso 1 1 d R . . O7 O 0.30790(10) 0.7864(3) 0.76756(15) 0.0264(5) Uani 1 1 d . . . O8 O 0.30833(10) 0.9638(3) 0.85595(16) 0.0285(6) Uani 1 1 d . . . O9 O 0.18810(11) 0.7768(3) 0.66103(17) 0.0339(6) Uani 1 1 d . . . O10 O 0.19019(11) 0.9469(3) 0.75491(16) 0.0304(6) Uani 1 1 d . . . O1W O 0.43781(19) 0.6829(4) 0.5057(3) 0.0775(12) Uani 1 1 d . . . H1WA H 0.4662 0.6583 0.5035 0.116 Uiso 1 1 d R . . H1WB H 0.4105 0.7244 0.4537 0.116 Uiso 1 1 d R . . O2W O 0.07300(18) 0.1096(4) 0.6034(3) 0.0904(13) Uani 1 1 d . . . H2WA H 0.0493 0.0651 0.6105 0.136 Uiso 1 1 d R . . H2WB H 0.0934 0.1721 0.6480 0.136 Uiso 1 1 d R . . N1 N 0.38177(12) 0.9702(3) 0.74589(18) 0.0234(6) Uani 1 1 d . . . H1A H 0.3551 0.9062 0.7411 0.028 Uiso 1 1 d R . . C1 C 0.41936(15) 0.8821(4) 0.7276(2) 0.0269(8) Uani 1 1 d . . . H1B H 0.4395 0.9496 0.7137 0.032 Uiso 1 1 d R . . H1C H 0.4491 0.8298 0.7849 0.032 Uiso 1 1 d R . . C2 C 0.34566(16) 1.0900(4) 0.6746(3) 0.0320(8) Uani 1 1 d . . . H2A H 0.3435 1.1718 0.7072 0.038 Uiso 1 1 d R . . H2B H 0.3674 1.1227 0.6515 0.038 Uiso 1 1 d R . . C3 C 0.42082(17) 1.0313(4) 0.8478(2) 0.0315(9) Uani 1 1 d . . . H3B H 0.3964 1.0869 0.8588 0.038 Uiso 1 1 d R . . H3C H 0.4375 0.9496 0.8916 0.038 Uiso 1 1 d R . . C4 C 0.47014(16) 1.1275(4) 0.8672(2) 0.0277(8) Uani 1 1 d . . . C5 C 0.52756(17) 1.0723(5) 0.9159(2) 0.0343(9) Uani 1 1 d . . . H5 H 0.5351 0.9750 0.9362 0.041 Uiso 1 1 calc R . . C6 C 0.57369(18) 1.1601(5) 0.9346(3) 0.0403(10) Uani 1 1 d . . . H6 H 0.6121 1.1224 0.9688 0.048 Uiso 1 1 calc R . . C7 C 0.56288(19) 1.3022(5) 0.9031(3) 0.0464(11) Uani 1 1 d . . . H7 H 0.5938 1.3607 0.9146 0.056 Uiso 1 1 calc R . . C8 C 0.50576(19) 1.3592(4) 0.8538(3) 0.0423(10) Uani 1 1 d . . . H8 H 0.4981 1.4554 0.8314 0.051 Uiso 1 1 calc R . . C9 C 0.46055(18) 1.2730(4) 0.8380(3) 0.0351(9) Uani 1 1 d . . . H9 H 0.4227 1.3130 0.8071 0.042 Uiso 1 1 calc R . . C10 C 0.28269(16) 0.8711(4) 0.7905(2) 0.0218(7) Uani 1 1 d . . . C11 C 0.21403(16) 0.8642(4) 0.7299(2) 0.0247(7) 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 Ce1 0.02438(11) 0.01238(10) 0.01855(10) -0.00019(7) 0.01474(8) -0.00058(8) P1 0.0224(5) 0.0190(4) 0.0213(4) -0.0003(3) 0.0138(4) 0.0020(4) P2 0.0263(5) 0.0128(4) 0.0214(4) -0.0003(3) 0.0157(4) -0.0004(4) O1 0.0315(14) 0.0232(14) 0.0328(13) 0.0029(10) 0.0226(12) 0.0003(11) O2 0.0250(13) 0.0238(14) 0.0229(11) 0.0022(10) 0.0143(11) 0.0011(10) O3 0.0331(15) 0.0378(16) 0.0348(14) 0.0062(11) 0.0248(13) 0.0138(12) O4 0.0294(14) 0.0156(13) 0.0371(14) 0.0033(10) 0.0175(12) 0.0000(10) O5 0.0493(16) 0.0162(12) 0.0270(12) 0.0014(10) 0.0279(13) 0.0043(11) O6 0.0381(15) 0.0185(13) 0.0343(13) 0.0047(10) 0.0269(12) 0.0055(11) O7 0.0305(14) 0.0280(14) 0.0266(12) -0.0066(10) 0.0203(12) 0.0017(11) O8 0.0258(14) 0.0292(14) 0.0302(13) -0.0140(11) 0.0165(12) -0.0024(11) O9 0.0326(15) 0.0351(16) 0.0396(14) -0.0216(12) 0.0247(13) -0.0111(12) O10 0.0288(14) 0.0328(15) 0.0351(13) -0.0142(11) 0.0220(12) -0.0014(12) O1W 0.119(3) 0.080(3) 0.082(3) 0.026(2) 0.086(3) 0.036(2) O2W 0.069(3) 0.106(3) 0.080(3) 0.006(2) 0.036(2) -0.029(2) N1 0.0228(15) 0.0241(16) 0.0259(14) -0.0057(12) 0.0159(13) -0.0070(12) C1 0.0218(18) 0.032(2) 0.0269(17) -0.0042(15) 0.0145(16) -0.0008(15) C2 0.028(2) 0.0221(19) 0.038(2) -0.0006(16) 0.0155(18) -0.0022(16) C3 0.041(2) 0.036(2) 0.0262(17) -0.0116(16) 0.0248(18) -0.0099(18) C4 0.030(2) 0.033(2) 0.0229(17) -0.0116(15) 0.0172(16) -0.0082(17) C5 0.039(2) 0.035(2) 0.0239(18) -0.0057(17) 0.0164(18) -0.0013(18) C6 0.025(2) 0.058(3) 0.033(2) -0.007(2) 0.0143(18) -0.002(2) C7 0.039(3) 0.050(3) 0.049(3) -0.011(2) 0.027(2) -0.016(2) C8 0.041(2) 0.030(2) 0.048(2) -0.0050(19) 0.022(2) -0.008(2) C9 0.033(2) 0.029(2) 0.037(2) -0.0104(17) 0.0184(19) -0.0039(17) C10 0.0322(19) 0.0194(18) 0.0212(16) -0.0010(14) 0.0200(16) -0.0015(15) C11 0.0310(19) 0.0217(18) 0.0267(17) -0.0050(15) 0.0201(16) -0.0050(16) _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 Ce1 O2 2.391(2) 7_566 ? Ce1 O1 2.416(2) . ? Ce1 O4 2.456(2) . ? Ce1 O8 2.491(2) 4_546 ? Ce1 O7 2.527(2) . ? Ce1 O5 2.538(2) 7_566 ? Ce1 O10 2.557(2) 4_546 ? Ce1 O9 2.568(2) . ? P1 O1 1.496(2) . ? P1 O2 1.498(2) . ? P1 O3 1.558(2) . ? P1 C1 1.821(3) . ? P2 O4 1.488(2) . ? P2 O5 1.512(2) . ? P2 O6 1.569(2) . ? P2 C2 1.832(4) . ? O2 Ce1 2.391(2) 7_566 ? O3 H3A 0.8519 . ? O5 Ce1 2.538(2) 7_566 ? O6 H6A 0.8535 . ? O7 C10 1.265(4) . ? O8 C10 1.249(4) . ? O8 Ce1 2.491(2) 4_556 ? O9 C11 1.253(4) . ? O10 C11 1.249(4) . ? O10 Ce1 2.557(2) 4_556 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8526 . ? O2W H2WA 0.8509 . ? O2W H2WB 0.8533 . ? N1 C2 1.504(4) . ? N1 C1 1.505(4) . ? N1 C3 1.538(4) . ? N1 H1A 0.9116 . ? C1 H1B 0.9618 . ? C1 H1C 0.9631 . ? C2 H2A 0.9636 . ? C2 H2B 0.9607 . ? C3 C4 1.495(5) . ? C3 H3B 0.9610 . ? C3 H3C 0.9640 . ? C4 C9 1.386(5) . ? C4 C5 1.389(5) . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 C7 1.367(6) . ? C6 H6 0.9300 . ? C7 C8 1.388(6) . ? C7 H7 0.9300 . ? C8 C9 1.372(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.547(5) . ? 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 O2 Ce1 O1 126.34(7) 7_566 . ? O2 Ce1 O4 78.03(8) 7_566 . ? O1 Ce1 O4 74.91(8) . . ? O2 Ce1 O8 84.50(7) 7_566 4_546 ? O1 Ce1 O8 137.46(8) . 4_546 ? O4 Ce1 O8 146.36(8) . 4_546 ? O2 Ce1 O7 135.72(8) 7_566 . ? O1 Ce1 O7 75.83(7) . . ? O4 Ce1 O7 71.86(8) . . ? O8 Ce1 O7 103.28(8) 4_546 . ? O2 Ce1 O5 73.46(8) 7_566 7_566 ? O1 Ce1 O5 84.84(8) . 7_566 ? O4 Ce1 O5 124.08(7) . 7_566 ? O8 Ce1 O5 76.55(8) 4_546 7_566 ? O7 Ce1 O5 150.82(8) . 7_566 ? O2 Ce1 O10 141.70(8) 7_566 4_546 ? O1 Ce1 O10 75.23(7) . 4_546 ? O4 Ce1 O10 140.12(8) . 4_546 ? O8 Ce1 O10 63.81(7) 4_546 4_546 ? O7 Ce1 O10 75.66(8) . 4_546 ? O5 Ce1 O10 78.42(8) 7_566 4_546 ? O2 Ce1 O9 79.38(8) 7_566 . ? O1 Ce1 O9 137.33(8) . . ? O4 Ce1 O9 79.47(8) . . ? O8 Ce1 O9 69.12(8) 4_546 . ? O7 Ce1 O9 63.94(7) . . ? O5 Ce1 O9 137.77(8) 7_566 . ? O10 Ce1 O9 106.28(8) 4_546 . ? O1 P1 O2 118.05(14) . . ? O1 P1 O3 110.64(14) . . ? O2 P1 O3 110.33(13) . . ? O1 P1 C1 106.20(15) . . ? O2 P1 C1 109.35(15) . . ? O3 P1 C1 100.76(15) . . ? O4 P2 O5 115.04(14) . . ? O4 P2 O6 110.01(14) . . ? O5 P2 O6 110.12(13) . . ? O4 P2 C2 109.97(15) . . ? O5 P2 C2 108.03(16) . . ? O6 P2 C2 102.98(16) . . ? P1 O1 Ce1 140.19(14) . . ? P1 O2 Ce1 146.23(14) . 7_566 ? P1 O3 H3A 108.8 . . ? P2 O4 Ce1 168.94(16) . . ? P2 O5 Ce1 113.52(12) . 7_566 ? P2 O6 H6A 108.3 . . ? C10 O7 Ce1 120.7(2) . . ? C10 O8 Ce1 122.3(2) . 4_556 ? C11 O9 Ce1 120.1(2) . . ? C11 O10 Ce1 120.0(2) . 4_556 ? H1WA O1W H1WB 109.4 . . ? H2WA O2W H2WB 109.5 . . ? C2 N1 C1 114.6(3) . . ? C2 N1 C3 111.2(3) . . ? C1 N1 C3 109.8(3) . . ? C2 N1 H1A 106.2 . . ? C1 N1 H1A 106.4 . . ? C3 N1 H1A 108.1 . . ? N1 C1 P1 115.7(2) . . ? N1 C1 H1B 108.1 . . ? P1 C1 H1B 108.0 . . ? N1 C1 H1C 108.7 . . ? P1 C1 H1C 108.3 . . ? H1B C1 H1C 107.8 . . ? N1 C2 P2 118.6(2) . . ? N1 C2 H2A 108.3 . . ? P2 C2 H2A 108.3 . . ? N1 C2 H2B 107.1 . . ? P2 C2 H2B 106.8 . . ? H2A C2 H2B 107.1 . . ? C4 C3 N1 113.1(3) . . ? C4 C3 H3B 108.8 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3C 109.2 . . ? N1 C3 H3C 108.4 . . ? H3B C3 H3C 108.0 . . ? C9 C4 C5 118.0(4) . . ? C9 C4 C3 121.8(4) . . ? C5 C4 C3 120.3(4) . . ? C6 C5 C4 120.9(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 119.9(4) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 121.3(4) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? O8 C10 O7 125.5(3) . . ? O8 C10 C11 117.0(3) . . ? O7 C10 C11 117.4(3) . . ? O10 C11 O9 126.7(3) . . ? O10 C11 C10 116.3(3) . . ? O9 C11 C10 116.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.589 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.104 # Attachment '- szg94(705730).cif' data_szg94 _database_code_depnum_ccdc_archive 'CCDC 705730' #TrackingRef '- szg94(705730).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N O12 P2 Pr' _chemical_formula_weight 559.11 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 '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 28.101(4) _cell_length_b 9.0522(13) _cell_length_c 17.536(3) _cell_angle_alpha 90.00 _cell_angle_beta 126.941(2) _cell_angle_gamma 90.00 _cell_volume 3565.1(9) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1614 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 23.11 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.083 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 2.977 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8534 _exptl_absorpt_correction_T_max 0.9374 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9786 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.49 _reflns_number_total 3687 _reflns_number_gt 2728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0262P)^2^+0.0000P] 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 3687 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 Pr1 Pr 0.247423(14) 0.63922(3) 0.61640(2) 0.01674(10) Uani 1 1 d . . . P1 P 0.37798(7) 0.74900(16) 0.62944(10) 0.0194(3) Uani 1 1 d . . . P2 P 0.26948(7) 1.04649(16) 0.56976(11) 0.0185(3) Uani 1 1 d . . . O1 O 0.34320(17) 0.6538(4) 0.6498(3) 0.0230(9) Uani 1 1 d . . . O2 O 0.34465(16) 0.8291(4) 0.5365(3) 0.0225(9) Uani 1 1 d . . . O3 O 0.43053(17) 0.6609(5) 0.6445(3) 0.0314(10) Uani 1 1 d . . . H3A H 0.4301 0.6728 0.5961 0.047 Uiso 1 1 d R . . O4 O 0.25482(17) 0.8926(4) 0.5776(3) 0.0249(9) Uani 1 1 d . . . O5 O 0.26462(18) 1.0810(4) 0.4813(3) 0.0262(10) Uani 1 1 d . . . O6 O 0.23045(17) 1.1581(4) 0.5793(3) 0.0253(9) Uani 1 1 d . . . H6A H 0.2320 1.2426 0.5598 0.038 Uiso 1 1 d R . . O7 O 0.30828(17) 0.7836(4) 0.7691(3) 0.0251(9) Uani 1 1 d . . . O8 O 0.30837(17) 0.9638(4) 0.8561(3) 0.0256(10) Uani 1 1 d . . . O9 O 0.18827(18) 0.7749(5) 0.6618(3) 0.0307(10) Uani 1 1 d . . . O10 O 0.19020(17) 0.9481(4) 0.7542(3) 0.0280(10) Uani 1 1 d . . . O1W O 0.4372(3) 0.6831(6) 0.5052(4) 0.0757(19) Uani 1 1 d . . . H1WA H 0.4655 0.6585 0.5030 0.114 Uiso 1 1 d R . . H1WB H 0.4098 0.7246 0.4532 0.114 Uiso 1 1 d R . . O2W O 0.0727(3) 0.1093(7) 0.6022(4) 0.086(2) Uani 1 1 d . . . H2WA H 0.0490 0.0648 0.6094 0.128 Uiso 1 1 d R . . H2WB H 0.0931 0.1718 0.6469 0.128 Uiso 1 1 d R . . N1 N 0.3813(2) 0.9696(5) 0.7460(3) 0.0225(11) Uani 1 1 d . . . H1A H 0.3546 0.9056 0.7411 0.027 Uiso 1 1 d R . . C1 C 0.4185(3) 0.8812(6) 0.7267(4) 0.0255(14) Uani 1 1 d . . . H1B H 0.4387 0.9487 0.7127 0.031 Uiso 1 1 d R . . H1C H 0.4482 0.8289 0.7839 0.031 Uiso 1 1 d R . . C2 C 0.3454(3) 1.0899(7) 0.6736(4) 0.0308(15) Uani 1 1 d . . . H2A H 0.3433 1.1718 0.7063 0.037 Uiso 1 1 d R . . H2B H 0.3672 1.1226 0.6505 0.037 Uiso 1 1 d R . . C3 C 0.4201(3) 1.0301(7) 0.8468(4) 0.0302(15) Uani 1 1 d . . . H3B H 0.3957 1.0857 0.8578 0.036 Uiso 1 1 d R . . H3C H 0.4368 0.9484 0.8905 0.036 Uiso 1 1 d R . . C4 C 0.4700(3) 1.1268(7) 0.8672(4) 0.0273(14) Uani 1 1 d . . . C5 C 0.5275(3) 1.0710(7) 0.9161(4) 0.0288(14) Uani 1 1 d . . . H5 H 0.5351 0.9734 0.9368 0.035 Uiso 1 1 calc R . . C6 C 0.5735(3) 1.1588(8) 0.9343(4) 0.0379(17) Uani 1 1 d . . . H6 H 0.6119 1.1205 0.9678 0.046 Uiso 1 1 calc R . . C7 C 0.5629(3) 1.3019(8) 0.9032(5) 0.0443(19) Uani 1 1 d . . . H7 H 0.5939 1.3605 0.9151 0.053 Uiso 1 1 calc R . . C8 C 0.5058(3) 1.3598(8) 0.8537(5) 0.0436(18) Uani 1 1 d . . . H8 H 0.4982 1.4565 0.8313 0.052 Uiso 1 1 calc R . . C9 C 0.4608(3) 1.2732(7) 0.8382(4) 0.0337(16) Uani 1 1 d . . . H9 H 0.4230 1.3137 0.8073 0.040 Uiso 1 1 calc R . . C10 C 0.2828(3) 0.8699(6) 0.7910(4) 0.0207(12) Uani 1 1 d . . . C11 C 0.2142(3) 0.8649(7) 0.7306(4) 0.0254(13) 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 Pr1 0.02333(18) 0.01240(15) 0.01834(16) -0.00025(14) 0.01457(14) -0.00058(14) P1 0.0219(9) 0.0183(8) 0.0209(8) 0.0005(6) 0.0144(7) 0.0039(6) P2 0.0258(9) 0.0118(8) 0.0209(8) -0.0007(6) 0.0156(7) -0.0004(6) O1 0.028(2) 0.019(2) 0.031(2) 0.0040(18) 0.022(2) 0.0003(18) O2 0.024(2) 0.024(2) 0.020(2) 0.0020(17) 0.0139(19) -0.0007(17) O3 0.030(3) 0.040(3) 0.032(2) 0.009(2) 0.022(2) 0.017(2) O4 0.021(2) 0.014(2) 0.033(2) 0.0025(17) 0.013(2) -0.0005(16) O5 0.042(3) 0.018(2) 0.026(2) 0.0013(17) 0.025(2) 0.0031(19) O6 0.035(3) 0.016(2) 0.034(2) 0.0063(17) 0.025(2) 0.0050(18) O7 0.029(3) 0.029(2) 0.024(2) -0.0064(18) 0.020(2) 0.0029(18) O8 0.025(2) 0.024(2) 0.029(2) -0.0125(18) 0.017(2) -0.0034(18) O9 0.030(3) 0.033(3) 0.034(3) -0.019(2) 0.022(2) -0.0111(19) O10 0.027(3) 0.033(3) 0.032(2) -0.0132(19) 0.021(2) 0.000(2) O1W 0.121(5) 0.079(5) 0.077(4) 0.027(3) 0.086(4) 0.035(4) O2W 0.063(4) 0.101(6) 0.079(5) 0.005(4) 0.036(4) -0.025(4) N1 0.022(3) 0.022(3) 0.028(3) -0.004(2) 0.017(3) -0.009(2) C1 0.022(3) 0.030(4) 0.027(3) -0.006(3) 0.015(3) -0.003(3) C2 0.027(4) 0.023(3) 0.034(4) -0.007(3) 0.013(3) -0.002(3) C3 0.036(4) 0.033(4) 0.027(3) -0.008(3) 0.021(3) -0.011(3) C4 0.025(4) 0.035(4) 0.022(3) -0.012(3) 0.014(3) -0.011(3) C5 0.029(4) 0.031(4) 0.018(3) -0.001(3) 0.010(3) -0.002(3) C6 0.028(4) 0.050(5) 0.032(4) -0.007(3) 0.016(3) 0.002(3) C7 0.035(5) 0.050(5) 0.053(5) -0.017(4) 0.029(4) -0.020(4) C8 0.039(5) 0.036(4) 0.051(5) -0.005(4) 0.024(4) -0.009(4) C9 0.029(4) 0.034(4) 0.036(4) -0.009(3) 0.018(3) -0.002(3) C10 0.031(3) 0.021(3) 0.020(3) 0.001(3) 0.020(3) -0.002(3) C11 0.029(4) 0.022(3) 0.032(3) -0.003(3) 0.022(3) -0.008(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 Pr1 O2 2.372(4) 7_566 ? Pr1 O1 2.390(4) . ? Pr1 O4 2.437(4) . ? Pr1 O8 2.474(4) 4_546 ? Pr1 O7 2.510(4) . ? Pr1 O5 2.515(4) 7_566 ? Pr1 O10 2.536(4) 4_546 ? Pr1 O9 2.549(4) . ? P1 O2 1.491(4) . ? P1 O1 1.498(4) . ? P1 O3 1.555(4) . ? P1 C1 1.817(6) . ? P2 O4 1.482(4) . ? P2 O5 1.506(4) . ? P2 O6 1.572(4) . ? P2 C2 1.831(6) . ? O2 Pr1 2.372(4) 7_566 ? O3 H3A 0.8499 . ? O5 Pr1 2.515(4) 7_566 ? O6 H6A 0.8498 . ? O7 C10 1.266(6) . ? O8 C10 1.247(6) . ? O8 Pr1 2.474(4) 4_556 ? O9 C11 1.263(7) . ? O10 C11 1.237(6) . ? O10 Pr1 2.536(4) 4_556 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8499 . ? O2W H2WA 0.8501 . ? O2W H2WB 0.8501 . ? N1 C2 1.509(7) . ? N1 C1 1.507(7) . ? N1 C3 1.516(7) . ? N1 H1A 0.9100 . ? C1 H1B 0.9599 . ? C1 H1C 0.9599 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C3 C4 1.501(8) . ? C3 H3B 0.9598 . ? C3 H3C 0.9600 . ? C4 C9 1.387(8) . ? C4 C5 1.392(8) . ? C5 C6 1.382(8) . ? C5 H5 0.9300 . ? C6 C7 1.367(9) . ? C6 H6 0.9300 . ? C7 C8 1.388(9) . ? C7 H7 0.9300 . ? C8 C9 1.369(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.544(8) . ? 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 O2 Pr1 O1 124.95(12) 7_566 . ? O2 Pr1 O4 77.81(12) 7_566 . ? O1 Pr1 O4 75.16(12) . . ? O2 Pr1 O8 84.79(12) 7_566 4_546 ? O1 Pr1 O8 137.74(13) . 4_546 ? O4 Pr1 O8 146.01(13) . 4_546 ? O2 Pr1 O7 136.39(13) 7_566 . ? O1 Pr1 O7 76.41(12) . . ? O4 Pr1 O7 71.94(13) . . ? O8 Pr1 O7 103.41(12) 4_546 . ? O2 Pr1 O5 73.55(13) 7_566 7_566 ? O1 Pr1 O5 83.18(13) . 7_566 ? O4 Pr1 O5 123.71(12) . 7_566 ? O8 Pr1 O5 77.41(12) 4_546 7_566 ? O7 Pr1 O5 149.99(13) . 7_566 ? O2 Pr1 O10 142.32(13) 7_566 4_546 ? O1 Pr1 O10 75.36(12) . 4_546 ? O4 Pr1 O10 139.71(13) . 4_546 ? O8 Pr1 O10 64.29(12) 4_546 4_546 ? O7 Pr1 O10 74.89(14) . 4_546 ? O5 Pr1 O10 78.83(13) 7_566 4_546 ? O2 Pr1 O9 79.74(13) 7_566 . ? O1 Pr1 O9 138.32(13) . . ? O4 Pr1 O9 79.33(13) . . ? O8 Pr1 O9 68.90(13) 4_546 . ? O7 Pr1 O9 64.52(12) . . ? O5 Pr1 O9 138.47(13) 7_566 . ? O10 Pr1 O9 106.21(13) 4_546 . ? O2 P1 O1 118.0(2) . . ? O2 P1 O3 110.1(2) . . ? O1 P1 O3 110.7(2) . . ? O2 P1 C1 109.4(3) . . ? O1 P1 C1 106.6(2) . . ? O3 P1 C1 100.5(2) . . ? O4 P2 O5 115.6(2) . . ? O4 P2 O6 110.1(2) . . ? O5 P2 O6 109.9(2) . . ? O4 P2 C2 109.4(3) . . ? O5 P2 C2 108.1(3) . . ? O6 P2 C2 103.1(3) . . ? P1 O1 Pr1 140.7(2) . . ? P1 O2 Pr1 146.7(2) . 7_566 ? P1 O3 H3A 108.9 . . ? P2 O4 Pr1 170.3(2) . . ? P2 O5 Pr1 115.4(2) . 7_566 ? P2 O6 H6A 109.1 . . ? C10 O7 Pr1 119.9(4) . . ? C10 O8 Pr1 122.1(4) . 4_556 ? C11 O9 Pr1 120.0(4) . . ? C11 O10 Pr1 119.5(4) . 4_556 ? H1WA O1W H1WB 109.5 . . ? H2WA O2W H2WB 109.5 . . ? C2 N1 C1 113.5(4) . . ? C2 N1 C3 111.6(5) . . ? C1 N1 C3 110.1(4) . . ? C2 N1 H1A 106.5 . . ? C1 N1 H1A 106.5 . . ? C3 N1 H1A 108.3 . . ? N1 C1 P1 115.6(4) . . ? N1 C1 H1B 108.3 . . ? P1 C1 H1B 108.3 . . ? N1 C1 H1C 108.2 . . ? P1 C1 H1C 108.5 . . ? H1B C1 H1C 107.7 . . ? N1 C2 P2 118.2(4) . . ? N1 C2 H2A 107.8 . . ? P2 C2 H2A 107.8 . . ? N1 C2 H2B 107.7 . . ? P2 C2 H2B 107.7 . . ? H2A C2 H2B 107.3 . . ? C4 C3 N1 113.8(4) . . ? C4 C3 H3B 108.9 . . ? N1 C3 H3B 108.9 . . ? C4 C3 H3C 108.7 . . ? N1 C3 H3C 108.5 . . ? H3B C3 H3C 107.9 . . ? C9 C4 C5 117.7(6) . . ? C9 C4 C3 121.9(6) . . ? C5 C4 C3 120.5(6) . . ? C6 C5 C4 120.8(6) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C6 C5 120.2(7) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.0(7) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 119.4(7) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C4 121.9(6) . . ? C8 C9 H9 119.1 . . ? C4 C9 H9 119.1 . . ? O8 C10 O7 125.3(5) . . ? O8 C10 C11 116.3(5) . . ? O7 C10 C11 118.3(5) . . ? O10 C11 O9 126.6(6) . . ? O10 C11 C10 117.3(5) . . ? O9 C11 C10 116.1(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.728 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.172 # Attachment '- szg95(705731) .cif' data_szg95 _database_code_depnum_ccdc_archive 'CCDC 705731' #TrackingRef '- szg95(705731) .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N Nd O12 P2' _chemical_formula_weight 562.44 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 '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 28.155(5) _cell_length_b 9.0228(14) _cell_length_c 17.505(3) _cell_angle_alpha 90.00 _cell_angle_beta 126.884(2) _cell_angle_gamma 90.00 _cell_volume 3556.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1113 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 20.76 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 3.164 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5862 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9758 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3679 _reflns_number_gt 2541 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0302P)^2^+0.0000P] 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 3679 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 Nd1 Nd 0.247486(17) 0.63913(4) 0.61720(3) 0.01774(11) Uani 1 1 d . . . P1 P 0.37699(8) 0.74779(19) 0.62839(13) 0.0199(4) Uani 1 1 d . . . P2 P 0.26895(8) 1.04622(19) 0.56947(13) 0.0194(4) Uani 1 1 d . . . O1 O 0.34227(19) 0.6541(5) 0.6497(3) 0.0244(11) Uani 1 1 d . . . O2 O 0.34354(19) 0.8295(5) 0.5356(3) 0.0221(11) Uani 1 1 d . . . O3 O 0.4293(2) 0.6589(5) 0.6434(3) 0.0316(12) Uani 1 1 d . . . H3A H 0.4289 0.6708 0.5950 0.047 Uiso 1 1 d R . . O4 O 0.2542(2) 0.8926(5) 0.5789(3) 0.0280(12) Uani 1 1 d . . . O5 O 0.2634(2) 1.0789(5) 0.4802(3) 0.0269(12) Uani 1 1 d . . . O6 O 0.23024(19) 1.1586(5) 0.5793(3) 0.0227(11) Uani 1 1 d . . . H6A H 0.2318 1.2432 0.5598 0.034 Uiso 1 1 d R . . O7 O 0.3082(2) 0.7823(5) 0.7695(3) 0.0240(11) Uani 1 1 d . . . O8 O 0.30873(19) 0.9623(5) 0.8577(3) 0.0236(11) Uani 1 1 d . . . O9 O 0.1884(2) 0.7729(5) 0.6614(3) 0.0309(12) Uani 1 1 d . . . O10 O 0.1905(2) 0.9492(5) 0.7551(3) 0.0268(12) Uani 1 1 d . . . O1W O 0.4358(3) 0.6814(7) 0.5044(5) 0.076(2) Uani 1 1 d . . . H1WA H 0.4641 0.6568 0.5022 0.114 Uiso 1 1 d R . . H1WB H 0.4085 0.7229 0.4523 0.114 Uiso 1 1 d R . . O2W O 0.0729(3) 0.1103(7) 0.6032(5) 0.087(2) Uani 1 1 d . . . H2WA H 0.0492 0.0658 0.6103 0.130 Uiso 1 1 d R . . H2WB H 0.0933 0.1728 0.6479 0.130 Uiso 1 1 d R . . N1 N 0.3807(2) 0.9692(6) 0.7452(4) 0.0224(13) Uani 1 1 d . . . H1A H 0.3541 0.9052 0.7404 0.027 Uiso 1 1 d R . . C1 C 0.4174(3) 0.8790(7) 0.7258(5) 0.0238(16) Uani 1 1 d . . . H1B H 0.4376 0.9465 0.7119 0.029 Uiso 1 1 d R . . H1C H 0.4472 0.8267 0.7830 0.029 Uiso 1 1 d R . . C2 C 0.3448(3) 1.0893(8) 0.6727(5) 0.0319(18) Uani 1 1 d . . . H2A H 0.3427 1.1712 0.7054 0.038 Uiso 1 1 d R . . H2B H 0.3665 1.1220 0.6497 0.038 Uiso 1 1 d R . . C3 C 0.4193(3) 1.0305(9) 0.8465(5) 0.0327(19) Uani 1 1 d . . . H3B H 0.3949 1.0861 0.8575 0.039 Uiso 1 1 d R . . H3C H 0.4360 0.9488 0.8902 0.039 Uiso 1 1 d R . . C4 C 0.4688(3) 1.1262(8) 0.8657(5) 0.0250(16) Uani 1 1 d . . . C5 C 0.5261(3) 1.0689(9) 0.9156(5) 0.0325(19) Uani 1 1 d . . . H5 H 0.5330 0.9711 0.9364 0.039 Uiso 1 1 calc R . . C6 C 0.5729(3) 1.1535(10) 0.9348(5) 0.040(2) Uani 1 1 d . . . H6 H 0.6110 1.1144 0.9694 0.048 Uiso 1 1 calc R . . C7 C 0.5618(3) 1.2987(9) 0.9014(6) 0.043(2) Uani 1 1 d . . . H7 H 0.5925 1.3558 0.9112 0.051 Uiso 1 1 calc R . . C8 C 0.5057(3) 1.3587(9) 0.8539(6) 0.042(2) Uani 1 1 d . . . H8 H 0.4988 1.4566 0.8331 0.051 Uiso 1 1 calc R . . C9 C 0.4603(3) 1.2741(8) 0.8377(6) 0.036(2) Uani 1 1 d . . . H9 H 0.4229 1.3161 0.8072 0.044 Uiso 1 1 calc R . . C10 C 0.2826(3) 0.8692(7) 0.7916(5) 0.0202(15) Uani 1 1 d . . . C11 C 0.2149(3) 0.8627(8) 0.7313(5) 0.0228(15) 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 Nd1 0.0263(2) 0.01161(18) 0.01931(19) -0.00043(17) 0.01584(17) -0.00075(18) P1 0.0224(10) 0.0176(9) 0.0208(10) 0.0003(8) 0.0135(9) 0.0013(8) P2 0.0276(10) 0.0115(9) 0.0209(9) 0.0007(7) 0.0155(9) -0.0007(8) O1 0.029(3) 0.017(3) 0.033(3) 0.003(2) 0.022(2) 0.002(2) O2 0.023(3) 0.018(3) 0.017(2) 0.000(2) 0.008(2) 0.001(2) O3 0.032(3) 0.036(3) 0.037(3) 0.009(3) 0.026(3) 0.015(2) O4 0.030(3) 0.013(2) 0.035(3) 0.001(2) 0.017(3) -0.003(2) O5 0.053(3) 0.012(2) 0.028(3) 0.000(2) 0.030(3) 0.001(2) O6 0.031(3) 0.015(2) 0.031(3) 0.005(2) 0.023(2) 0.007(2) O7 0.027(3) 0.025(3) 0.025(3) -0.005(2) 0.019(2) 0.004(2) O8 0.023(3) 0.020(3) 0.025(3) -0.008(2) 0.013(2) 0.000(2) O9 0.033(3) 0.030(3) 0.034(3) -0.016(2) 0.022(3) -0.008(2) O10 0.027(3) 0.024(3) 0.034(3) -0.014(2) 0.021(3) -0.004(2) O1W 0.124(6) 0.073(5) 0.088(5) 0.030(4) 0.094(5) 0.034(4) O2W 0.065(5) 0.092(6) 0.080(5) 0.003(5) 0.030(4) -0.028(4) N1 0.028(3) 0.021(3) 0.022(3) -0.002(3) 0.017(3) -0.006(3) C1 0.022(4) 0.029(4) 0.020(4) -0.007(3) 0.013(3) 0.002(3) C2 0.036(4) 0.024(4) 0.038(5) -0.002(4) 0.023(4) -0.004(4) C3 0.042(5) 0.040(5) 0.026(4) -0.012(4) 0.026(4) -0.012(4) C4 0.028(4) 0.027(4) 0.026(4) -0.013(3) 0.019(4) -0.006(3) C5 0.041(5) 0.031(4) 0.021(4) -0.004(3) 0.017(4) 0.000(4) C6 0.023(4) 0.059(6) 0.031(4) -0.009(4) 0.012(4) 0.003(4) C7 0.029(5) 0.042(5) 0.053(6) -0.018(4) 0.022(5) -0.016(4) C8 0.039(5) 0.025(4) 0.048(5) -0.001(4) 0.019(4) -0.001(4) C9 0.026(4) 0.026(4) 0.047(5) -0.011(4) 0.016(4) -0.005(4) C10 0.034(4) 0.016(3) 0.021(4) 0.001(3) 0.022(3) -0.003(3) C11 0.032(4) 0.017(4) 0.026(4) -0.006(3) 0.021(4) -0.011(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 Nd1 O2 2.361(4) 7_566 ? Nd1 O1 2.375(4) . ? Nd1 O4 2.423(4) . ? Nd1 O8 2.466(4) 4_546 ? Nd1 O7 2.496(4) . ? Nd1 O5 2.498(4) 7_566 ? Nd1 O10 2.510(4) 4_546 ? Nd1 O9 2.523(5) . ? P1 O2 1.493(4) . ? P1 O1 1.499(5) . ? P1 O3 1.554(5) . ? P1 C1 1.810(6) . ? P2 O4 1.484(4) . ? P2 O5 1.503(5) . ? P2 O6 1.572(4) . ? P2 C2 1.829(7) . ? O2 Nd1 2.361(4) 7_566 ? O3 H3A 0.8484 . ? O5 Nd1 2.498(4) 7_566 ? O6 H6A 0.8474 . ? O7 C10 1.272(7) . ? O8 C10 1.250(7) . ? O8 Nd1 2.466(4) 4_556 ? O9 C11 1.271(7) . ? O10 C11 1.264(8) . ? O10 Nd1 2.510(4) 4_556 ? O1W H1WA 0.8512 . ? O1W H1WB 0.8495 . ? O2W H2WA 0.8504 . ? O2W H2WB 0.8487 . ? N1 C2 1.506(8) . ? N1 C1 1.506(8) . ? N1 C3 1.523(8) . ? N1 H1A 0.9100 . ? C1 H1B 0.9591 . ? C1 H1C 0.9593 . ? C2 H2A 0.9576 . ? C2 H2B 0.9600 . ? C3 C4 1.496(9) . ? C3 H3B 0.9597 . ? C3 H3C 0.9578 . ? C4 C9 1.392(10) . ? C4 C5 1.394(10) . ? C5 C6 1.377(10) . ? C5 H5 0.9300 . ? C6 C7 1.392(11) . ? C6 H6 0.9300 . ? C7 C8 1.380(10) . ? C7 H7 0.9300 . ? C8 C9 1.364(10) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.529(9) . ? 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 O2 Nd1 O1 124.33(16) 7_566 . ? O2 Nd1 O4 77.58(15) 7_566 . ? O1 Nd1 O4 75.49(15) . . ? O2 Nd1 O8 84.46(15) 7_566 4_546 ? O1 Nd1 O8 138.02(15) . 4_546 ? O4 Nd1 O8 145.62(16) . 4_546 ? O2 Nd1 O7 136.89(14) 7_566 . ? O1 Nd1 O7 76.35(15) . . ? O4 Nd1 O7 71.95(15) . . ? O8 Nd1 O7 104.21(15) 4_546 . ? O2 Nd1 O5 73.49(15) 7_566 7_566 ? O1 Nd1 O5 82.45(16) . 7_566 ? O4 Nd1 O5 123.52(16) . 7_566 ? O8 Nd1 O5 77.49(15) 4_546 7_566 ? O7 Nd1 O5 149.48(15) . 7_566 ? O2 Nd1 O10 142.47(15) 7_566 4_546 ? O1 Nd1 O10 75.17(15) . 4_546 ? O4 Nd1 O10 139.74(15) . 4_546 ? O8 Nd1 O10 65.01(15) 4_546 4_546 ? O7 Nd1 O10 74.78(15) . 4_546 ? O5 Nd1 O10 78.76(15) 7_566 4_546 ? O2 Nd1 O9 79.81(15) 7_566 . ? O1 Nd1 O9 138.76(15) . . ? O4 Nd1 O9 78.96(16) . . ? O8 Nd1 O9 69.09(16) 4_546 . ? O7 Nd1 O9 65.15(15) . . ? O5 Nd1 O9 138.78(15) 7_566 . ? O10 Nd1 O9 106.76(16) 4_546 . ? O2 P1 O1 118.0(3) . . ? O2 P1 O3 110.7(3) . . ? O1 P1 O3 111.1(3) . . ? O2 P1 C1 109.3(3) . . ? O1 P1 C1 105.7(3) . . ? O3 P1 C1 100.4(3) . . ? O4 P2 O5 115.9(3) . . ? O4 P2 O6 109.4(3) . . ? O5 P2 O6 109.9(3) . . ? O4 P2 C2 109.1(3) . . ? O5 P2 C2 108.5(3) . . ? O6 P2 C2 103.3(3) . . ? P1 O1 Nd1 141.2(3) . . ? P1 O2 Nd1 147.0(3) . 7_566 ? P1 O3 H3A 108.8 . . ? P2 O4 Nd1 170.4(3) . . ? P2 O5 Nd1 116.7(2) . 7_566 ? P2 O6 H6A 109.3 . . ? C10 O7 Nd1 119.6(4) . . ? C10 O8 Nd1 121.0(4) . 4_556 ? C11 O9 Nd1 119.1(4) . . ? C11 O10 Nd1 119.3(4) . 4_556 ? H1WA O1W H1WB 109.7 . . ? H2WA O2W H2WB 109.5 . . ? C2 N1 C1 113.8(5) . . ? C2 N1 C3 111.6(5) . . ? C1 N1 C3 110.6(5) . . ? C2 N1 H1A 106.2 . . ? C1 N1 H1A 106.0 . . ? C3 N1 H1A 108.1 . . ? N1 C1 P1 115.9(4) . . ? N1 C1 H1B 107.8 . . ? P1 C1 H1B 108.1 . . ? N1 C1 H1C 108.5 . . ? P1 C1 H1C 108.9 . . ? H1B C1 H1C 107.4 . . ? N1 C2 P2 118.4(5) . . ? N1 C2 H2A 107.7 . . ? P2 C2 H2A 107.5 . . ? N1 C2 H2B 107.5 . . ? P2 C2 H2B 108.1 . . ? H2A C2 H2B 107.4 . . ? C4 C3 N1 112.8(6) . . ? C4 C3 H3B 109.7 . . ? N1 C3 H3B 109.1 . . ? C4 C3 H3C 108.7 . . ? N1 C3 H3C 108.4 . . ? H3B C3 H3C 108.0 . . ? C9 C4 C5 117.7(7) . . ? C9 C4 C3 122.3(7) . . ? C5 C4 C3 119.9(7) . . ? C6 C5 C4 121.7(7) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 118.6(7) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C8 120.6(8) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.7(7) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 121.5(7) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? O8 C10 O7 124.7(6) . . ? O8 C10 C11 117.5(6) . . ? O7 C10 C11 117.8(6) . . ? O9 C11 O10 126.2(6) . . ? O9 C11 C10 117.2(6) . . ? O10 C11 C10 116.6(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.851 _refine_diff_density_min -0.814 _refine_diff_density_rms 0.202 # Attachment '- szg96(705732).cif' data_szg96 _database_code_depnum_ccdc_archive 'CCDC 705732' #TrackingRef '- szg96(705732).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N O12 P2 Sm' _chemical_formula_weight 568.55 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 '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 28.210(5) _cell_length_b 8.9618(15) _cell_length_c 17.405(3) _cell_angle_alpha 90.00 _cell_angle_beta 126.717(2) _cell_angle_gamma 90.00 _cell_volume 3527.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1031 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 19.59 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 3.576 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5067 _exptl_absorpt_correction_T_max 0.8643 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9368 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3454 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0299P)^2^+0.0000P] 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 3454 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 Sm1 Sm 0.247626(17) 0.63932(4) 0.61852(3) 0.01903(13) Uani 1 1 d . . . P1 P 0.37472(9) 0.7460(2) 0.62591(14) 0.0222(5) Uani 1 1 d . . . P2 P 0.26817(9) 1.0454(2) 0.56927(14) 0.0199(4) Uani 1 1 d . . . O1 O 0.3401(2) 0.6531(5) 0.6476(4) 0.0263(12) Uani 1 1 d . . . O2 O 0.3417(2) 0.8296(5) 0.5332(3) 0.0220(12) Uani 1 1 d . . . O3 O 0.4261(2) 0.6540(5) 0.6406(4) 0.0333(13) Uani 1 1 d . . . H3A H 0.4257 0.6659 0.5921 0.050 Uiso 1 1 d R . . O4 O 0.2540(2) 0.8924(5) 0.5818(4) 0.0253(13) Uani 1 1 d . . . O5 O 0.2627(2) 1.0743(5) 0.4789(3) 0.0285(13) Uani 1 1 d . . . O6 O 0.2300(2) 1.1599(5) 0.5789(3) 0.0259(12) Uani 1 1 d . . . H6A H 0.2315 1.2444 0.5594 0.039 Uiso 1 1 d R . . O7 O 0.3081(2) 0.7799(6) 0.7714(4) 0.0278(13) Uani 1 1 d . . . O8 O 0.3081(2) 0.9623(5) 0.8582(3) 0.0261(12) Uani 1 1 d . . . O9 O 0.1897(2) 0.7722(6) 0.6634(4) 0.0298(13) Uani 1 1 d . . . O10 O 0.1912(2) 0.9488(5) 0.7555(4) 0.0303(13) Uani 1 1 d . . . O1W O 0.4328(3) 0.6770(7) 0.5005(5) 0.076(2) Uani 1 1 d . . . H1WA H 0.4611 0.6524 0.4983 0.113 Uiso 1 1 d R . . H1WB H 0.4055 0.7185 0.4484 0.113 Uiso 1 1 d R . . O2W O 0.0744(3) 0.1086(8) 0.6042(5) 0.085(3) Uani 1 1 d . . . H2WA H 0.0507 0.0641 0.6113 0.128 Uiso 1 1 d R . . H2WB H 0.0948 0.1711 0.6489 0.128 Uiso 1 1 d R . . N1 N 0.3795(3) 0.9690(7) 0.7433(4) 0.0264(16) Uani 1 1 d . . . H1A H 0.3529 0.9051 0.7385 0.032 Uiso 1 1 d R . . C1 C 0.4154(3) 0.8776(8) 0.7241(5) 0.0253(18) Uani 1 1 d . . . H1B H 0.4356 0.9452 0.7102 0.030 Uiso 1 1 d R . . H1C H 0.4452 0.8254 0.7813 0.030 Uiso 1 1 d R . . C2 C 0.3434(3) 1.0907(8) 0.6703(6) 0.030(2) Uani 1 1 d . . . H2A H 0.3413 1.1725 0.7030 0.036 Uiso 1 1 d R . . H2B H 0.3652 1.1234 0.6472 0.036 Uiso 1 1 d R . . C3 C 0.4185(4) 1.0308(9) 0.8460(6) 0.032(2) Uani 1 1 d . . . H3B H 0.3941 1.0864 0.8570 0.038 Uiso 1 1 d R . . H3C H 0.4352 0.9492 0.8898 0.038 Uiso 1 1 d R . . C4 C 0.4684(3) 1.1236(9) 0.8656(5) 0.0278(19) Uani 1 1 d . . . C5 C 0.5249(4) 1.0638(10) 0.9150(6) 0.035(2) Uani 1 1 d . . . H5 H 0.5314 0.9651 0.9356 0.042 Uiso 1 1 calc R . . C6 C 0.5716(4) 1.1501(11) 0.9338(6) 0.043(2) Uani 1 1 d . . . H6 H 0.6094 1.1097 0.9675 0.051 Uiso 1 1 calc R . . C7 C 0.5617(4) 1.2973(10) 0.9023(7) 0.045(2) Uani 1 1 d . . . H7 H 0.5928 1.3554 0.9144 0.054 Uiso 1 1 calc R . . C8 C 0.5065(4) 1.3558(9) 0.8538(6) 0.042(2) Uani 1 1 d . . . H8 H 0.4997 1.4530 0.8307 0.050 Uiso 1 1 calc R . . C9 C 0.4603(4) 1.2732(9) 0.8383(6) 0.037(2) Uani 1 1 d . . . H9 H 0.4235 1.3175 0.8094 0.044 Uiso 1 1 calc R . . C10 C 0.2828(3) 0.8663(8) 0.7918(5) 0.0233(17) Uani 1 1 d . . . C11 C 0.2149(3) 0.8620(8) 0.7320(6) 0.0234(17) 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 Sm1 0.0283(2) 0.01333(19) 0.0205(2) -0.00020(18) 0.01731(19) -0.00071(18) P1 0.0272(11) 0.0196(10) 0.0232(11) -0.0005(8) 0.0169(10) 0.0009(9) P2 0.0289(11) 0.0136(10) 0.0223(11) -0.0019(8) 0.0181(10) -0.0004(8) O1 0.038(3) 0.017(3) 0.036(3) 0.003(2) 0.029(3) -0.001(2) O2 0.029(3) 0.018(3) 0.019(3) 0.002(2) 0.014(3) -0.001(2) O3 0.037(3) 0.035(3) 0.031(3) 0.002(3) 0.022(3) 0.013(3) O4 0.030(3) 0.011(3) 0.029(3) 0.002(2) 0.014(3) -0.005(2) O5 0.050(4) 0.019(3) 0.025(3) -0.003(2) 0.028(3) -0.002(3) O6 0.039(3) 0.017(3) 0.031(3) 0.002(2) 0.026(3) 0.004(2) O7 0.030(3) 0.030(3) 0.029(3) -0.007(2) 0.020(3) 0.000(2) O8 0.030(3) 0.028(3) 0.026(3) -0.006(2) 0.019(3) 0.003(2) O9 0.037(3) 0.031(3) 0.035(3) -0.019(3) 0.029(3) -0.012(3) O10 0.029(3) 0.024(3) 0.041(4) -0.016(3) 0.022(3) -0.005(2) O1W 0.109(6) 0.085(5) 0.087(6) 0.029(4) 0.088(6) 0.037(5) O2W 0.068(5) 0.096(6) 0.075(6) -0.002(5) 0.034(5) -0.027(5) N1 0.030(4) 0.025(3) 0.023(4) -0.010(3) 0.015(3) -0.010(3) C1 0.032(4) 0.024(4) 0.024(4) 0.001(3) 0.019(4) 0.000(3) C2 0.031(5) 0.019(4) 0.037(5) 0.001(3) 0.019(4) 0.003(3) C3 0.044(5) 0.030(4) 0.032(5) -0.014(4) 0.028(5) -0.008(4) C4 0.031(4) 0.041(5) 0.018(4) -0.016(4) 0.018(4) -0.008(4) C5 0.037(5) 0.040(5) 0.025(5) 0.000(4) 0.017(5) 0.004(4) C6 0.028(5) 0.070(7) 0.032(5) -0.013(5) 0.019(5) 0.000(5) C7 0.046(6) 0.041(6) 0.045(6) -0.011(5) 0.025(5) -0.013(5) C8 0.045(6) 0.029(5) 0.046(6) -0.004(4) 0.025(5) -0.011(5) C9 0.029(5) 0.028(5) 0.049(6) -0.009(4) 0.020(5) -0.003(4) C10 0.033(4) 0.023(4) 0.018(4) 0.007(4) 0.017(4) 0.000(4) C11 0.029(4) 0.017(4) 0.037(5) -0.002(4) 0.027(4) -0.005(4) _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 Sm1 O2 2.333(5) 7_566 ? Sm1 O1 2.346(5) . ? Sm1 O4 2.392(4) . ? Sm1 O8 2.433(5) 4_546 ? Sm1 O5 2.456(5) 7_566 ? Sm1 O7 2.480(5) . ? Sm1 O10 2.485(5) 4_546 ? Sm1 O9 2.494(5) . ? P1 O1 1.493(5) . ? P1 O2 1.495(5) . ? P1 O3 1.550(5) . ? P1 C1 1.812(7) . ? P2 O4 1.480(5) . ? P2 O5 1.509(5) . ? P2 O6 1.568(5) . ? P2 C2 1.817(8) . ? O2 Sm1 2.333(5) 7_566 ? O3 H3A 0.8435 . ? O5 Sm1 2.456(5) 7_566 ? O6 H6A 0.8419 . ? O7 C10 1.241(9) . ? O8 C10 1.264(8) . ? O8 Sm1 2.433(5) 4_556 ? O9 C11 1.251(8) . ? O10 C11 1.244(8) . ? O10 Sm1 2.485(5) 4_556 ? O1W H1WA 0.8521 . ? O1W H1WB 0.8480 . ? O2W H2WA 0.8499 . ? O2W H2WB 0.8452 . ? N1 C1 1.488(9) . ? N1 C2 1.514(9) . ? N1 C3 1.537(9) . ? N1 H1A 0.9090 . ? C1 H1B 0.9562 . ? C1 H1C 0.9573 . ? C2 H2A 0.9516 . ? C2 H2B 0.9580 . ? C3 C4 1.490(10) . ? C3 H3B 0.9581 . ? C3 H3C 0.9527 . ? C4 C5 1.387(11) . ? C4 C9 1.395(10) . ? C5 C6 1.388(11) . ? C5 H5 0.9300 . ? C6 C7 1.392(12) . ? C6 H6 0.9300 . ? C7 C8 1.358(12) . ? C7 H7 0.9300 . ? C8 C9 1.377(11) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.538(10) . ? 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 O2 Sm1 O1 123.13(18) 7_566 . ? O2 Sm1 O4 77.72(16) 7_566 . ? O1 Sm1 O4 75.87(16) . . ? O2 Sm1 O8 84.18(17) 7_566 4_546 ? O1 Sm1 O8 138.17(16) . 4_546 ? O4 Sm1 O8 145.32(18) . 4_546 ? O2 Sm1 O5 73.10(16) 7_566 7_566 ? O1 Sm1 O5 81.25(17) . 7_566 ? O4 Sm1 O5 123.50(17) . 7_566 ? O8 Sm1 O5 77.55(17) 4_546 7_566 ? O2 Sm1 O7 137.60(16) 7_566 . ? O1 Sm1 O7 77.26(17) . . ? O4 Sm1 O7 72.03(17) . . ? O8 Sm1 O7 104.53(17) 4_546 . ? O5 Sm1 O7 149.13(17) 7_566 . ? O2 Sm1 O10 142.28(16) 7_566 4_546 ? O1 Sm1 O10 75.52(17) . 4_546 ? O4 Sm1 O10 139.77(16) . 4_546 ? O8 Sm1 O10 65.29(17) 4_546 4_546 ? O5 Sm1 O10 78.85(17) 7_566 4_546 ? O7 Sm1 O10 74.52(18) . 4_546 ? O2 Sm1 O9 80.32(17) 7_566 . ? O1 Sm1 O9 139.44(16) . . ? O4 Sm1 O9 78.40(17) . . ? O8 Sm1 O9 69.49(17) 4_546 . ? O5 Sm1 O9 139.31(17) 7_566 . ? O7 Sm1 O9 65.18(17) . . ? O10 Sm1 O9 106.91(18) 4_546 . ? O1 P1 O2 118.1(3) . . ? O1 P1 O3 110.5(3) . . ? O2 P1 O3 111.3(3) . . ? O1 P1 C1 105.5(3) . . ? O2 P1 C1 109.0(3) . . ? O3 P1 C1 100.8(3) . . ? O4 P2 O5 116.4(3) . . ? O4 P2 O6 109.1(3) . . ? O5 P2 O6 110.6(3) . . ? O4 P2 C2 109.0(3) . . ? O5 P2 C2 107.6(4) . . ? O6 P2 C2 103.3(3) . . ? P1 O1 Sm1 141.8(3) . . ? P1 O2 Sm1 146.8(3) . 7_566 ? P1 O3 H3A 108.4 . . ? P2 O4 Sm1 171.0(3) . . ? P2 O5 Sm1 118.8(3) . 7_566 ? P2 O6 H6A 110.0 . . ? C10 O7 Sm1 118.7(5) . . ? C10 O8 Sm1 121.8(5) . 4_556 ? C11 O9 Sm1 120.1(5) . . ? C11 O10 Sm1 119.6(5) . 4_556 ? H1WA O1W H1WB 110.1 . . ? H2WA O2W H2WB 109.8 . . ? C1 N1 C2 114.4(6) . . ? C1 N1 C3 110.5(6) . . ? C2 N1 C3 111.8(6) . . ? C1 N1 H1A 105.6 . . ? C2 N1 H1A 105.8 . . ? C3 N1 H1A 108.2 . . ? N1 C1 P1 115.9(5) . . ? N1 C1 H1B 107.3 . . ? P1 C1 H1B 108.1 . . ? N1 C1 H1C 109.1 . . ? P1 C1 H1C 109.3 . . ? H1B C1 H1C 106.8 . . ? N1 C2 P2 117.5(5) . . ? N1 C2 H2A 107.7 . . ? P2 C2 H2A 107.2 . . ? N1 C2 H2B 107.1 . . ? P2 C2 H2B 109.5 . . ? H2A C2 H2B 107.4 . . ? C4 C3 N1 112.8(6) . . ? C4 C3 H3B 111.1 . . ? N1 C3 H3B 108.7 . . ? C4 C3 H3C 107.4 . . ? N1 C3 H3C 108.7 . . ? H3B C3 H3C 108.1 . . ? C5 C4 C9 118.5(8) . . ? C5 C4 C3 120.3(8) . . ? C9 C4 C3 121.2(7) . . ? C6 C5 C4 120.4(8) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.9(8) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.7(9) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.9(8) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C4 120.4(8) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? O7 C10 O8 125.3(7) . . ? O7 C10 C11 119.1(7) . . ? O8 C10 C11 115.6(7) . . ? O10 C11 O9 127.4(7) . . ? O10 C11 C10 117.2(7) . . ? O9 C11 C10 115.4(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.788 _refine_diff_density_min -0.950 _refine_diff_density_rms 0.191 # Attachment '- szg97(705733).cif' data_szg97 _database_code_depnum_ccdc_archive 'CCDC 705733' #TrackingRef '- szg97(705733).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Eu N O12 P2' _chemical_formula_weight 570.16 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 '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 28.298(3) _cell_length_b 8.9336(9) _cell_length_c 17.3809(18) _cell_angle_alpha 90.00 _cell_angle_beta 126.5920(10) _cell_angle_gamma 90.00 _cell_volume 3527.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2784 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 3.802 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5168 _exptl_absorpt_correction_T_max 0.8848 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9134 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3452 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0294P)^2^+0.0000P] 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 3452 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Eu1 Eu 0.247646(10) 0.63889(2) 0.619041(15) 0.01606(8) Uani 1 1 d . . . P1 P 0.37353(5) 0.74473(13) 0.62457(8) 0.0189(3) Uani 1 1 d . . . P2 P 0.26804(5) 1.04507(13) 0.56955(8) 0.0175(3) Uani 1 1 d . . . O1 O 0.33888(14) 0.6516(3) 0.6460(2) 0.0238(7) Uani 1 1 d . . . O2 O 0.34085(14) 0.8292(3) 0.5318(2) 0.0224(7) Uani 1 1 d . . . O3 O 0.42458(15) 0.6519(4) 0.6384(2) 0.0313(8) Uani 1 1 d . . . H3A H 0.4242 0.6638 0.5900 0.047 Uiso 1 1 d R . . O4 O 0.25432(14) 0.8916(3) 0.5830(2) 0.0245(7) Uani 1 1 d . . . O5 O 0.26168(14) 1.0740(3) 0.4781(2) 0.0233(7) Uani 1 1 d . . . O6 O 0.23016(15) 1.1607(3) 0.5793(2) 0.0246(7) Uani 1 1 d . . . H6A H 0.2317 1.2452 0.5598 0.037 Uiso 1 1 d R . . O7 O 0.30799(14) 0.7775(3) 0.7713(2) 0.0237(7) Uani 1 1 d . . . O8 O 0.30833(14) 0.9610(4) 0.8594(2) 0.0245(7) Uani 1 1 d . . . O9 O 0.18993(15) 0.7708(4) 0.6632(2) 0.0285(8) Uani 1 1 d . . . O10 O 0.19172(14) 0.9492(4) 0.7558(2) 0.0269(8) Uani 1 1 d . . . O1W O 0.4305(2) 0.6746(5) 0.4975(3) 0.0661(14) Uani 1 1 d . . . H1WA H 0.4589 0.6500 0.4953 0.099 Uiso 1 1 d R . . H1WB H 0.4032 0.7161 0.4454 0.099 Uiso 1 1 d R . . O2W O 0.0749(2) 0.1067(5) 0.6055(3) 0.0771(15) Uani 1 1 d . . . H2WA H 0.0512 0.0622 0.6126 0.116 Uiso 1 1 d R . . H2WB H 0.0953 0.1692 0.6501 0.116 Uiso 1 1 d R . . N1 N 0.37905(17) 0.9684(4) 0.7436(3) 0.0214(9) Uani 1 1 d . . . H1A H 0.3524 0.9044 0.7388 0.026 Uiso 1 1 d R . . C1 C 0.4150(2) 0.8770(5) 0.7233(3) 0.0249(11) Uani 1 1 d . . . H1B H 0.4352 0.9445 0.7094 0.030 Uiso 1 1 d R . . H1C H 0.4448 0.8247 0.7806 0.030 Uiso 1 1 d R . . C2 C 0.3435(2) 1.0893(5) 0.6708(4) 0.0282(11) Uani 1 1 d . . . H2A H 0.3414 1.1711 0.7034 0.034 Uiso 1 1 d R . . H2B H 0.3652 1.1220 0.6477 0.034 Uiso 1 1 d R . . C3 C 0.4175(2) 1.0299(6) 0.8453(3) 0.0305(12) Uani 1 1 d . . . H3B H 0.3931 1.0855 0.8563 0.037 Uiso 1 1 d R . . H3C H 0.4342 0.9482 0.8891 0.037 Uiso 1 1 d R . . C4 C 0.4680(2) 1.1227(5) 0.8655(3) 0.0237(11) Uani 1 1 d . . . C5 C 0.5242(2) 1.0623(6) 0.9143(3) 0.0319(12) Uani 1 1 d . . . H5 H 0.5305 0.9633 0.9347 0.038 Uiso 1 1 calc R . . C6 C 0.5708(2) 1.1470(7) 0.9331(4) 0.0381(14) Uani 1 1 d . . . H6 H 0.6082 1.1052 0.9662 0.046 Uiso 1 1 calc R . . C7 C 0.5618(2) 1.2931(7) 0.9031(4) 0.0390(14) Uani 1 1 d . . . H7 H 0.5931 1.3504 0.9158 0.047 Uiso 1 1 calc R . . C8 C 0.5063(2) 1.3550(6) 0.8540(4) 0.0397(14) Uani 1 1 d . . . H8 H 0.5003 1.4533 0.8324 0.048 Uiso 1 1 calc R . . C9 C 0.4595(2) 1.2723(6) 0.8367(4) 0.0323(12) Uani 1 1 d . . . H9 H 0.4226 1.3161 0.8060 0.039 Uiso 1 1 calc R . . C10 C 0.2831(2) 0.8662(5) 0.7938(3) 0.0191(10) Uani 1 1 d . . . C11 C 0.2156(2) 0.8609(5) 0.7319(3) 0.0205(10) 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 Eu1 0.02530(14) 0.01005(12) 0.01743(12) 0.00013(10) 0.01522(10) -0.00032(10) P1 0.0238(7) 0.0164(6) 0.0196(6) 0.0000(5) 0.0146(5) 0.0026(5) P2 0.0260(7) 0.0109(6) 0.0193(6) -0.0003(5) 0.0155(5) -0.0002(5) O1 0.0295(19) 0.0195(18) 0.0300(18) 0.0030(15) 0.0219(16) 0.0001(15) O2 0.0297(19) 0.0182(18) 0.0230(16) 0.0015(14) 0.0177(15) 0.0004(15) O3 0.037(2) 0.036(2) 0.0318(18) 0.0060(17) 0.0263(17) 0.0122(17) O4 0.0283(19) 0.0147(17) 0.0286(17) 0.0050(14) 0.0159(16) 0.0009(14) O5 0.044(2) 0.0125(16) 0.0239(17) 0.0006(14) 0.0257(16) 0.0029(15) O6 0.039(2) 0.0155(18) 0.0280(17) 0.0051(14) 0.0251(16) 0.0055(15) O7 0.0322(19) 0.0221(18) 0.0244(17) 0.0005(14) 0.0210(16) 0.0069(15) O8 0.0289(19) 0.0202(18) 0.0271(17) -0.0077(15) 0.0181(16) -0.0011(15) O9 0.037(2) 0.0257(19) 0.0304(19) -0.0161(16) 0.0242(17) -0.0112(16) O10 0.0316(19) 0.026(2) 0.0297(18) -0.0097(16) 0.0220(16) 0.0001(16) O1W 0.101(4) 0.068(3) 0.071(3) 0.023(3) 0.074(3) 0.030(3) O2W 0.068(3) 0.080(4) 0.073(3) -0.006(3) 0.036(3) -0.027(3) N1 0.027(2) 0.019(2) 0.026(2) -0.0077(18) 0.0198(19) -0.0106(18) C1 0.022(3) 0.032(3) 0.022(2) -0.001(2) 0.014(2) 0.001(2) C2 0.026(3) 0.017(2) 0.037(3) -0.005(2) 0.017(2) -0.004(2) C3 0.039(3) 0.034(3) 0.022(2) -0.009(2) 0.020(2) -0.006(3) C4 0.026(3) 0.027(3) 0.019(2) -0.011(2) 0.014(2) -0.008(2) C5 0.036(3) 0.034(3) 0.019(2) -0.002(2) 0.012(2) -0.001(3) C6 0.022(3) 0.054(4) 0.033(3) -0.007(3) 0.014(2) 0.002(3) C7 0.031(3) 0.042(4) 0.043(3) -0.009(3) 0.021(3) -0.011(3) C8 0.039(3) 0.029(3) 0.047(3) -0.004(3) 0.023(3) -0.009(3) C9 0.022(3) 0.032(3) 0.037(3) -0.011(3) 0.014(2) -0.005(2) C10 0.026(2) 0.019(2) 0.017(2) 0.002(2) 0.015(2) -0.001(2) C11 0.029(3) 0.016(2) 0.025(2) -0.001(2) 0.021(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 Eu1 O2 2.324(3) 7_566 ? Eu1 O1 2.336(3) . ? Eu1 O4 2.380(3) . ? Eu1 O8 2.426(3) 4_546 ? Eu1 O5 2.451(3) 7_566 ? Eu1 O7 2.463(3) . ? Eu1 O10 2.469(3) 4_546 ? Eu1 O9 2.478(3) . ? Eu1 C10 3.249(4) 4_546 ? Eu1 P2 3.4507(12) 7_566 ? P1 O1 1.492(3) . ? P1 O2 1.498(3) . ? P1 O3 1.555(3) . ? P1 C1 1.821(5) . ? P2 O4 1.481(3) . ? P2 O5 1.511(3) . ? P2 O6 1.569(3) . ? P2 C2 1.825(5) . ? P2 Eu1 3.4507(12) 7_566 ? O2 Eu1 2.324(3) 7_566 ? O3 H3A 0.8423 . ? O5 Eu1 2.451(3) 7_566 ? O6 H6A 0.8396 . ? O7 C10 1.267(5) . ? O8 C10 1.247(5) . ? O8 Eu1 2.426(3) 4_556 ? O9 C11 1.252(5) . ? O10 C11 1.260(5) . ? O10 Eu1 2.469(3) 4_556 ? O1W H1WA 0.8542 . ? O1W H1WB 0.8489 . ? O2W H2WA 0.8508 . ? O2W H2WB 0.8447 . ? N1 C1 1.502(6) . ? N1 C2 1.504(6) . ? N1 C3 1.523(5) . ? N1 H1A 0.9098 . ? C1 H1B 0.9558 . ? C1 H1C 0.9580 . ? C2 H2A 0.9493 . ? C2 H2B 0.9585 . ? C3 C4 1.503(7) . ? C3 H3B 0.9587 . ? C3 H3C 0.9510 . ? C4 C5 1.389(7) . ? C4 C9 1.397(7) . ? C5 C6 1.379(7) . ? C5 H5 0.9300 . ? C6 C7 1.372(8) . ? C6 H6 0.9300 . ? C7 C8 1.380(8) . ? C7 H7 0.9300 . ? C8 C9 1.382(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.536(7) . ? C10 Eu1 3.249(4) 4_556 ? 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 O2 Eu1 O1 122.63(10) 7_566 . ? O2 Eu1 O4 77.75(11) 7_566 . ? O1 Eu1 O4 75.82(11) . . ? O2 Eu1 O8 83.75(11) 7_566 4_546 ? O1 Eu1 O8 138.29(10) . 4_546 ? O4 Eu1 O8 145.45(11) . 4_546 ? O2 Eu1 O5 73.55(11) 7_566 7_566 ? O1 Eu1 O5 80.11(11) . 7_566 ? O4 Eu1 O5 123.20(10) . 7_566 ? O8 Eu1 O5 77.66(10) 4_546 7_566 ? O2 Eu1 O7 137.84(10) 7_566 . ? O1 Eu1 O7 77.55(10) . . ? O4 Eu1 O7 72.11(10) . . ? O8 Eu1 O7 105.16(10) 4_546 . ? O5 Eu1 O7 148.37(10) 7_566 . ? O2 Eu1 O10 142.54(11) 7_566 4_546 ? O1 Eu1 O10 75.64(10) . 4_546 ? O4 Eu1 O10 139.48(11) . 4_546 ? O8 Eu1 O10 65.74(11) 4_546 4_546 ? O5 Eu1 O10 78.88(10) 7_566 4_546 ? O7 Eu1 O10 74.10(11) . 4_546 ? O2 Eu1 O9 79.93(11) 7_566 . ? O1 Eu1 O9 140.21(11) . . ? O4 Eu1 O9 78.49(11) . . ? O8 Eu1 O9 69.63(11) 4_546 . ? O5 Eu1 O9 139.68(11) 7_566 . ? O7 Eu1 O9 65.85(10) . . ? O10 Eu1 O9 107.10(11) 4_546 . ? O2 Eu1 C10 102.13(11) 7_566 4_546 ? O1 Eu1 C10 120.95(11) . 4_546 ? O4 Eu1 C10 156.78(11) . 4_546 ? O8 Eu1 C10 19.20(11) 4_546 4_546 ? O5 Eu1 C10 77.92(10) 7_566 4_546 ? O7 Eu1 C10 94.76(11) . 4_546 ? O10 Eu1 C10 46.65(11) 4_546 4_546 ? O9 Eu1 C10 78.64(11) . 4_546 ? O2 Eu1 P2 62.92(8) 7_566 7_566 ? O1 Eu1 P2 73.42(8) . 7_566 ? O4 Eu1 P2 100.80(8) . 7_566 ? O8 Eu1 P2 96.25(8) 4_546 7_566 ? O5 Eu1 P2 22.46(7) 7_566 7_566 ? O7 Eu1 P2 150.97(7) . 7_566 ? O10 Eu1 P2 97.94(8) 4_546 7_566 ? O9 Eu1 P2 141.76(8) . 7_566 ? C10 Eu1 P2 99.63(8) 4_546 7_566 ? O1 P1 O2 118.24(19) . . ? O1 P1 O3 110.60(18) . . ? O2 P1 O3 110.84(18) . . ? O1 P1 C1 106.0(2) . . ? O2 P1 C1 109.0(2) . . ? O3 P1 C1 100.5(2) . . ? O4 P2 O5 116.53(18) . . ? O4 P2 O6 109.39(18) . . ? O5 P2 O6 109.90(17) . . ? O4 P2 C2 108.3(2) . . ? O5 P2 C2 108.3(2) . . ? O6 P2 C2 103.6(2) . . ? O4 P2 Eu1 79.16(13) . 7_566 ? O5 P2 Eu1 38.32(12) . 7_566 ? O6 P2 Eu1 134.99(13) . 7_566 ? C2 P2 Eu1 115.63(17) . 7_566 ? P1 O1 Eu1 142.11(19) . . ? P1 O2 Eu1 146.57(19) . 7_566 ? P1 O3 H3A 108.7 . . ? P2 O4 Eu1 171.5(2) . . ? P2 O5 Eu1 119.22(17) . 7_566 ? P2 O6 H6A 110.2 . . ? C10 O7 Eu1 119.3(3) . . ? C10 O8 Eu1 121.0(3) . 4_556 ? C11 O9 Eu1 119.1(3) . . ? C11 O10 Eu1 119.5(3) . 4_556 ? H1WA O1W H1WB 110.4 . . ? H2WA O2W H2WB 109.9 . . ? C1 N1 C2 113.6(3) . . ? C1 N1 C3 110.7(4) . . ? C2 N1 C3 112.0(4) . . ? C1 N1 H1A 106.1 . . ? C2 N1 H1A 105.7 . . ? C3 N1 H1A 108.2 . . ? N1 C1 P1 115.3(3) . . ? N1 C1 H1B 107.9 . . ? P1 C1 H1B 108.5 . . ? N1 C1 H1C 108.7 . . ? P1 C1 H1C 109.6 . . ? H1B C1 H1C 106.4 . . ? N1 C2 P2 117.9(3) . . ? N1 C2 H2A 107.3 . . ? P2 C2 H2A 106.8 . . ? N1 C2 H2B 107.3 . . ? P2 C2 H2B 109.7 . . ? H2A C2 H2B 107.5 . . ? C4 C3 N1 113.0(4) . . ? C4 C3 H3B 111.5 . . ? N1 C3 H3B 108.5 . . ? C4 C3 H3C 106.7 . . ? N1 C3 H3C 108.8 . . ? H3B C3 H3C 108.1 . . ? C5 C4 C9 118.7(5) . . ? C5 C4 C3 120.7(5) . . ? C9 C4 C3 120.5(5) . . ? C6 C5 C4 121.0(5) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 119.9(5) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.0(5) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.6(5) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 119.7(5) . . ? C8 C9 H9 120.2 . . ? C4 C9 H9 120.2 . . ? O8 C10 O7 125.9(4) . . ? O8 C10 C11 117.1(4) . . ? O7 C10 C11 116.9(4) . . ? O8 C10 Eu1 39.8(2) . 4_556 ? O7 C10 Eu1 164.9(3) . 4_556 ? C11 C10 Eu1 77.4(2) . 4_556 ? O9 C11 O10 126.6(4) . . ? O9 C11 C10 117.4(4) . . ? O10 C11 C10 116.0(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.638 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.137 # Attachment '- szg98(705734).cif' data_szg98 _database_code_depnum_ccdc_archive 'CCDC 705734' #TrackingRef '- szg98(705734).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Gd N O12 P2' _chemical_formula_weight 575.45 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 '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 28.425(17) _cell_length_b 8.924(5) _cell_length_c 17.391(10) _cell_angle_alpha 90.00 _cell_angle_beta 126.617(7) _cell_angle_gamma 90.00 _cell_volume 3541(4) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1445 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 21.07 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 3.992 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5502 _exptl_absorpt_correction_T_max 0.7928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9327 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3469 _reflns_number_gt 2547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. The final difference Fourier maps showed residual peaks of 2.553 e \%A^-3^ (1.00 \%A from Gd1 atom) and holes of -0.91 e \%A^-3^(1.04 \%A from O2 atom). The relatively higher residuals are due to the absorption correction problems with the heavy Gd(III) ions. ; _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^)+(0.0441P)^2^+0.0000P] 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 3469 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Gd1 Gd 0.247790(16) 0.63886(4) 0.61962(3) 0.01862(13) Uani 1 1 d . . . P1 P 0.37277(9) 0.7443(2) 0.62380(14) 0.0221(4) Uani 1 1 d . . . P2 P 0.26772(9) 1.0447(2) 0.56905(14) 0.0220(5) Uani 1 1 d . . . O1 O 0.3382(2) 0.6520(5) 0.6458(4) 0.0249(12) Uani 1 1 d . . . O2 O 0.3404(2) 0.8287(6) 0.5311(4) 0.0238(12) Uani 1 1 d . . . O3 O 0.4232(2) 0.6508(6) 0.6373(4) 0.0340(14) Uani 1 1 d . . . H3A H 0.4228 0.6627 0.5888 0.051 Uiso 1 1 d R . . O4 O 0.2544(2) 0.8924(5) 0.5838(4) 0.0246(12) Uani 1 1 d . . . O5 O 0.2607(2) 1.0717(6) 0.4773(4) 0.0290(13) Uani 1 1 d . . . O6 O 0.2307(2) 1.1623(6) 0.5799(4) 0.0297(13) Uani 1 1 d . . . H6A H 0.2323 1.2468 0.5604 0.044 Uiso 1 1 d R . . O7 O 0.3078(2) 0.7768(6) 0.7717(3) 0.0256(12) Uani 1 1 d . . . O8 O 0.3084(2) 0.9604(6) 0.8598(4) 0.0260(13) Uani 1 1 d . . . O9 O 0.1905(2) 0.7688(6) 0.6637(4) 0.0307(14) Uani 1 1 d . . . O10 O 0.1917(2) 0.9495(6) 0.7555(4) 0.0293(13) Uani 1 1 d . . . O1W O 0.4295(4) 0.6739(8) 0.4962(5) 0.069(2) Uani 1 1 d . . . H1WA H 0.4578 0.6493 0.4940 0.103 Uiso 1 1 d R . . H1WB H 0.4022 0.7155 0.4441 0.103 Uiso 1 1 d R . . O2W O 0.0745(4) 0.1078(9) 0.6049(6) 0.085(3) Uani 1 1 d . . . H2WA H 0.0508 0.0633 0.6121 0.128 Uiso 1 1 d R . . H2WB H 0.0949 0.1703 0.6496 0.128 Uiso 1 1 d R . . N1 N 0.3787(3) 0.9675(7) 0.7433(4) 0.0244(15) Uani 1 1 d . . . H1A H 0.3520 0.9035 0.7385 0.029 Uiso 1 1 d R . . C1 C 0.4145(3) 0.8758(9) 0.7229(6) 0.0300(19) Uani 1 1 d . . . H1B H 0.4347 0.9433 0.7089 0.036 Uiso 1 1 d R . . H1C H 0.4442 0.8235 0.7801 0.036 Uiso 1 1 d R . . C2 C 0.3434(3) 1.0911(9) 0.6706(6) 0.033(2) Uani 1 1 d . . . H2A H 0.3413 1.1729 0.7033 0.039 Uiso 1 1 d R . . H2B H 0.3652 1.1238 0.6475 0.039 Uiso 1 1 d R . . C3 C 0.4177(4) 1.0303(10) 0.8457(6) 0.034(2) Uani 1 1 d . . . H3B H 0.3932 1.0859 0.8567 0.041 Uiso 1 1 d R . . H3C H 0.4343 0.9487 0.8894 0.041 Uiso 1 1 d R . . C4 C 0.4678(3) 1.1222(10) 0.8654(6) 0.031(2) Uani 1 1 d . . . C5 C 0.5227(4) 1.0609(11) 0.9130(6) 0.039(2) Uani 1 1 d . . . H5 H 0.5284 0.9610 0.9318 0.047 Uiso 1 1 calc R . . C6 C 0.5702(4) 1.1458(11) 0.9338(6) 0.040(2) Uani 1 1 d . . . H6 H 0.6075 1.1040 0.9679 0.048 Uiso 1 1 calc R . . C7 C 0.5611(4) 1.2934(11) 0.9029(7) 0.047(3) Uani 1 1 d . . . H7 H 0.5923 1.3508 0.9156 0.056 Uiso 1 1 calc R . . C8 C 0.5069(4) 1.3536(11) 0.8545(7) 0.043(2) Uani 1 1 d . . . H8 H 0.5012 1.4519 0.8328 0.052 Uiso 1 1 calc R . . C9 C 0.4598(4) 1.2735(10) 0.8365(6) 0.036(2) Uani 1 1 d . . . H9 H 0.4232 1.3186 0.8056 0.043 Uiso 1 1 calc R . . C10 C 0.2833(3) 0.8652(8) 0.7939(5) 0.0184(15) Uani 1 1 d . . . C11 C 0.2164(3) 0.8602(9) 0.7333(5) 0.0239(17) 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 Gd1 0.0287(2) 0.0115(2) 0.0194(2) -0.00041(16) 0.01630(17) -0.00076(17) P1 0.0269(11) 0.0202(11) 0.0223(11) -0.0002(8) 0.0163(9) 0.0010(9) P2 0.0339(11) 0.0140(11) 0.0231(11) -0.0005(8) 0.0197(9) -0.0011(9) O1 0.033(3) 0.019(3) 0.031(3) 0.003(2) 0.024(3) 0.002(2) O2 0.029(3) 0.024(3) 0.022(3) 0.000(2) 0.017(2) -0.004(2) O3 0.038(3) 0.033(4) 0.038(3) 0.006(3) 0.026(3) 0.013(3) O4 0.031(3) 0.009(3) 0.030(3) 0.005(2) 0.016(3) 0.004(2) O5 0.051(4) 0.019(3) 0.024(3) 0.004(2) 0.026(3) 0.004(3) O6 0.046(3) 0.020(3) 0.035(3) 0.007(2) 0.030(3) 0.009(3) O7 0.035(3) 0.027(3) 0.021(3) -0.003(2) 0.021(3) 0.003(2) O8 0.029(3) 0.022(3) 0.025(3) -0.008(2) 0.015(3) 0.001(2) O9 0.034(3) 0.031(4) 0.033(3) -0.017(3) 0.023(3) -0.009(3) O10 0.032(3) 0.028(3) 0.031(3) -0.011(3) 0.021(3) 0.000(3) O1W 0.109(6) 0.063(5) 0.074(5) 0.021(4) 0.077(5) 0.027(5) O2W 0.076(6) 0.095(7) 0.079(6) -0.005(5) 0.043(5) -0.029(5) N1 0.030(4) 0.026(4) 0.024(4) -0.006(3) 0.019(3) -0.011(3) C1 0.026(4) 0.034(5) 0.026(4) -0.003(4) 0.013(4) 0.000(4) C2 0.031(4) 0.022(5) 0.039(5) -0.002(4) 0.018(4) -0.006(4) C3 0.039(5) 0.034(5) 0.027(5) -0.013(4) 0.019(4) -0.014(4) C4 0.029(4) 0.044(6) 0.023(4) -0.004(4) 0.017(4) -0.006(4) C5 0.034(5) 0.042(6) 0.027(5) -0.007(4) 0.010(4) -0.001(4) C6 0.036(5) 0.054(7) 0.026(5) -0.006(5) 0.016(4) 0.000(5) C7 0.040(6) 0.043(6) 0.051(6) -0.015(5) 0.024(5) -0.013(5) C8 0.040(5) 0.039(6) 0.049(6) 0.002(5) 0.026(5) -0.008(5) C9 0.031(5) 0.038(6) 0.033(5) -0.014(4) 0.016(4) -0.009(4) C10 0.034(4) 0.013(4) 0.023(4) 0.003(3) 0.025(4) 0.002(3) C11 0.034(4) 0.019(4) 0.022(4) -0.001(3) 0.018(4) -0.008(4) _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 Gd1 O2 2.324(5) 7_566 ? Gd1 O1 2.330(5) . ? Gd1 O4 2.384(5) . ? Gd1 O8 2.429(5) 4_546 ? Gd1 O5 2.438(5) 7_566 ? Gd1 O7 2.457(5) . ? Gd1 O9 2.465(5) . ? Gd1 O10 2.465(5) 4_546 ? P1 O1 1.496(5) . ? P1 O2 1.498(5) . ? P1 O3 1.551(6) . ? P1 C1 1.820(8) . ? P2 O4 1.474(5) . ? P2 O5 1.504(5) . ? P2 O6 1.575(5) . ? P2 C2 1.841(8) . ? O2 Gd1 2.324(5) 7_566 ? O3 H3A 0.8427 . ? O5 Gd1 2.438(5) 7_566 ? O6 H6A 0.8390 . ? O7 C10 1.254(8) . ? O8 C10 1.252(8) . ? O8 Gd1 2.429(5) 4_556 ? O9 C11 1.269(9) . ? O10 C11 1.265(9) . ? O10 Gd1 2.465(5) 4_556 ? O1W H1WA 0.8577 . ? O1W H1WB 0.8497 . ? O2W H2WA 0.8534 . ? O2W H2WB 0.8447 . ? N1 C1 1.504(10) . ? N1 C2 1.519(10) . ? N1 C3 1.536(9) . ? N1 H1A 0.9122 . ? C1 H1B 0.9575 . ? C1 H1C 0.9588 . ? C2 H2A 0.9492 . ? C2 H2B 0.9608 . ? C3 C4 1.496(11) . ? C3 H3B 0.9611 . ? C3 H3C 0.9506 . ? C4 C5 1.372(11) . ? C4 C9 1.411(12) . ? C5 C6 1.394(13) . ? C5 H5 0.9300 . ? C6 C7 1.387(13) . ? C6 H6 0.9300 . ? C7 C8 1.351(12) . ? C7 H7 0.9300 . ? C8 C9 1.379(12) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.531(11) . ? 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 O2 Gd1 O1 122.48(18) 7_566 . ? O2 Gd1 O4 77.74(17) 7_566 . ? O1 Gd1 O4 75.73(17) . . ? O2 Gd1 O8 83.43(18) 7_566 4_546 ? O1 Gd1 O8 138.59(17) . 4_546 ? O4 Gd1 O8 145.30(18) . 4_546 ? O2 Gd1 O5 73.83(18) 7_566 7_566 ? O1 Gd1 O5 79.41(18) . 7_566 ? O4 Gd1 O5 122.78(18) . 7_566 ? O8 Gd1 O5 78.15(18) 4_546 7_566 ? O2 Gd1 O7 137.78(18) 7_566 . ? O1 Gd1 O7 77.75(17) . . ? O4 Gd1 O7 72.13(18) . . ? O8 Gd1 O7 105.36(18) 4_546 . ? O5 Gd1 O7 148.10(17) 7_566 . ? O2 Gd1 O9 79.81(18) 7_566 . ? O1 Gd1 O9 140.53(18) . . ? O4 Gd1 O9 78.73(19) . . ? O8 Gd1 O9 69.36(19) 4_546 . ? O5 Gd1 O9 140.05(18) 7_566 . ? O7 Gd1 O9 65.97(17) . . ? O2 Gd1 O10 142.72(18) 7_566 4_546 ? O1 Gd1 O10 75.72(17) . 4_546 ? O4 Gd1 O10 139.32(17) . 4_546 ? O8 Gd1 O10 66.14(18) 4_546 4_546 ? O5 Gd1 O10 79.05(18) 7_566 4_546 ? O7 Gd1 O10 73.95(19) . 4_546 ? O9 Gd1 O10 106.97(19) . 4_546 ? O1 P1 O2 118.5(3) . . ? O1 P1 O3 110.7(3) . . ? O2 P1 O3 110.6(3) . . ? O1 P1 C1 105.6(4) . . ? O2 P1 C1 109.3(3) . . ? O3 P1 C1 100.5(3) . . ? O4 P2 O5 116.6(3) . . ? O4 P2 O6 109.6(3) . . ? O5 P2 O6 110.1(3) . . ? O4 P2 C2 108.3(3) . . ? O5 P2 C2 108.8(4) . . ? O6 P2 C2 102.6(4) . . ? P1 O1 Gd1 142.5(3) . . ? P1 O2 Gd1 146.4(3) . 7_566 ? P1 O3 H3A 108.8 . . ? P2 O4 Gd1 171.6(3) . . ? P2 O5 Gd1 120.4(3) . 7_566 ? P2 O6 H6A 110.6 . . ? C10 O7 Gd1 119.3(5) . . ? C10 O8 Gd1 120.9(4) . 4_556 ? C11 O9 Gd1 119.0(5) . . ? C11 O10 Gd1 118.5(5) . 4_556 ? H1WA O1W H1WB 110.5 . . ? H2WA O2W H2WB 110.0 . . ? C1 N1 C2 113.7(6) . . ? C1 N1 C3 110.5(6) . . ? C2 N1 C3 111.2(6) . . ? C1 N1 H1A 106.2 . . ? C2 N1 H1A 106.2 . . ? C3 N1 H1A 108.7 . . ? N1 C1 P1 115.1(5) . . ? N1 C1 H1B 108.0 . . ? P1 C1 H1B 108.4 . . ? N1 C1 H1C 108.8 . . ? P1 C1 H1C 110.0 . . ? H1B C1 H1C 106.1 . . ? N1 C2 P2 116.6(5) . . ? N1 C2 H2A 107.8 . . ? P2 C2 H2A 107.0 . . ? N1 C2 H2B 107.4 . . ? P2 C2 H2B 110.0 . . ? H2A C2 H2B 107.6 . . ? C4 C3 N1 113.3(7) . . ? C4 C3 H3B 112.0 . . ? N1 C3 H3B 108.2 . . ? C4 C3 H3C 106.5 . . ? N1 C3 H3C 108.6 . . ? H3B C3 H3C 108.1 . . ? C5 C4 C9 118.7(8) . . ? C5 C4 C3 120.4(9) . . ? C9 C4 C3 121.0(8) . . ? C4 C5 C6 121.1(9) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 119.2(9) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C6 119.9(9) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.8(9) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C4 119.2(8) . . ? C8 C9 H9 120.4 . . ? C4 C9 H9 120.4 . . ? O8 C10 O7 126.2(7) . . ? O8 C10 C11 116.4(6) . . ? O7 C10 C11 117.4(7) . . ? O10 C11 O9 125.7(7) . . ? O10 C11 C10 117.4(7) . . ? O9 C11 C10 116.8(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.553 _refine_diff_density_min -0.914 _refine_diff_density_rms 0.192 # Attachment '- szg99(705735).cif' data_szg99 _database_code_depnum_ccdc_archive 'CCDC 705735' #TrackingRef '- szg99(705735).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N O12 P2 Tb' _chemical_formula_weight 577.12 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 '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 28.391(7) _cell_length_b 8.890(2) _cell_length_c 17.309(4) _cell_angle_alpha 90.00 _cell_angle_beta 126.430(4) _cell_angle_gamma 90.00 _cell_volume 3515.0(15) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 455 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 18.18 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 4.271 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6282 _exptl_absorpt_correction_T_max 0.7182 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Smart Apex II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6713 _diffrn_reflns_av_R_equivalents 0.1262 _diffrn_reflns_av_sigmaI/netI 0.1361 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 22.26 _reflns_number_total 2221 _reflns_number_gt 1374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0240P)^2^+0.0000P] 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 2221 _refine_ls_number_parameters 244 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.973 _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 Tb1 Tb 0.24775(3) 0.63922(7) 0.61984(5) 0.0206(2) Uani 1 1 d . . . P1 P 0.37198(17) 0.7430(4) 0.6230(3) 0.0217(10) Uani 1 1 d . . . P2 P 0.26746(17) 1.0435(4) 0.5687(3) 0.0220(10) Uani 1 1 d . . . O1 O 0.3368(3) 0.6492(10) 0.6446(6) 0.026(2) Uani 1 1 d . . . O2 O 0.3394(4) 0.8288(9) 0.5292(6) 0.024(2) Uani 1 1 d . . . O3 O 0.4229(3) 0.6479(10) 0.6371(6) 0.033(2) Uani 1 1 d . . . H3A H 0.4225 0.6598 0.5887 0.049 Uiso 1 1 d R . . O4 O 0.2541(4) 0.8900(9) 0.5844(6) 0.027(2) Uani 1 1 d . . . O5 O 0.2604(4) 1.0720(10) 0.4757(6) 0.028(3) Uani 1 1 d . . . O6 O 0.2309(3) 1.1620(9) 0.5803(5) 0.026(2) Uani 1 1 d U . . H6A H 0.2324 1.2466 0.5609 0.039 Uiso 1 1 d R . . O7 O 0.3083(4) 0.7766(9) 0.7726(6) 0.024(2) Uani 1 1 d . . . O8 O 0.3075(4) 0.9612(10) 0.8592(6) 0.027(3) Uani 1 1 d . . . O9 O 0.1909(4) 0.7688(10) 0.6650(7) 0.030(3) Uani 1 1 d . . . O10 O 0.1921(4) 0.9495(10) 0.7558(6) 0.026(2) Uani 1 1 d . . . O1W O 0.4290(5) 0.6722(12) 0.4959(8) 0.075(4) Uani 1 1 d . . . H1WA H 0.4573 0.6476 0.4937 0.112 Uiso 1 1 d R . . H1WB H 0.4017 0.7137 0.4438 0.112 Uiso 1 1 d R . . O2W O 0.0758(5) 0.1063(12) 0.6051(8) 0.077(4) Uani 1 1 d . . . H2WA H 0.0520 0.0617 0.6122 0.115 Uiso 1 1 d R . . H2WB H 0.0962 0.1687 0.6497 0.115 Uiso 1 1 d R . . N1 N 0.3785(5) 0.9685(12) 0.7426(8) 0.031(3) Uani 1 1 d . . . H1A H 0.3518 0.9045 0.7377 0.037 Uiso 1 1 d R . . C1 C 0.4136(5) 0.8740(17) 0.7219(9) 0.029(4) Uani 1 1 d . . . H1B H 0.4338 0.9415 0.7079 0.034 Uiso 1 1 d R . . H1C H 0.4434 0.8217 0.7791 0.034 Uiso 1 1 d R . . C2 C 0.3433(5) 1.0887(14) 0.6699(10) 0.030(4) Uani 1 1 d . . . H2A H 0.3412 1.1706 0.7026 0.035 Uiso 1 1 d R . . H2B H 0.3650 1.1214 0.6468 0.035 Uiso 1 1 d R . . C3 C 0.4170(7) 1.0299(17) 0.8460(11) 0.039(5) Uani 1 1 d . . . H3B H 0.3925 1.0855 0.8570 0.047 Uiso 1 1 d R . . H3C H 0.4336 0.9482 0.8897 0.047 Uiso 1 1 d R . . C4 C 0.4677(6) 1.1183(19) 0.8657(10) 0.033(4) Uani 1 1 d . . . C5 C 0.5232(7) 1.0606(17) 0.9130(11) 0.034(4) Uani 1 1 d . . . H5 H 0.5290 0.9599 0.9311 0.040 Uiso 1 1 calc R . . C6 C 0.5709(7) 1.144(2) 0.9352(11) 0.049(4) Uani 1 1 d . . . H6 H 0.6083 1.1022 0.9703 0.058 Uiso 1 1 calc R . . C7 C 0.5615(8) 1.289(2) 0.9038(11) 0.048(5) Uani 1 1 d . . . H7 H 0.5925 1.3466 0.9158 0.058 Uiso 1 1 calc R . . C8 C 0.5061(7) 1.3513(19) 0.8544(11) 0.041(4) Uani 1 1 d . . . H8 H 0.5001 1.4496 0.8319 0.049 Uiso 1 1 calc R . . C9 C 0.4599(7) 1.2698(17) 0.8380(11) 0.044(5) Uani 1 1 d . . . H9 H 0.4235 1.3150 0.8087 0.053 Uiso 1 1 calc R . . C10 C 0.2825(5) 0.8659(17) 0.7949(9) 0.019(3) Uani 1 1 d U . . C11 C 0.2157(6) 0.8617(18) 0.7326(9) 0.019(3) Uani 1 1 d U . . 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 Tb1 0.0336(4) 0.0136(4) 0.0219(5) -0.0003(5) 0.0204(4) -0.0005(5) P1 0.028(2) 0.019(2) 0.021(3) -0.0008(19) 0.017(2) 0.003(2) P2 0.037(3) 0.014(2) 0.026(3) -0.0019(19) 0.025(3) 0.002(2) O1 0.033(5) 0.022(5) 0.027(6) 0.012(5) 0.020(5) 0.001(6) O2 0.044(6) 0.015(6) 0.031(7) -0.008(5) 0.032(6) -0.003(5) O3 0.042(6) 0.041(6) 0.027(6) 0.010(6) 0.026(5) 0.015(6) O4 0.044(6) 0.014(6) 0.024(6) 0.009(4) 0.020(6) 0.005(5) O5 0.041(6) 0.023(6) 0.023(7) 0.004(5) 0.022(6) 0.001(5) O6 0.043(5) 0.008(5) 0.033(6) 0.009(4) 0.026(5) 0.006(4) O7 0.031(6) 0.021(6) 0.027(7) -0.009(5) 0.022(6) -0.003(5) O8 0.043(7) 0.020(6) 0.022(7) -0.012(5) 0.021(6) -0.013(5) O9 0.044(7) 0.024(6) 0.039(8) -0.009(5) 0.034(6) -0.010(5) O10 0.038(6) 0.023(6) 0.023(7) -0.004(5) 0.021(6) -0.004(5) O1W 0.130(11) 0.072(9) 0.089(10) 0.028(8) 0.102(10) 0.025(9) O2W 0.080(9) 0.063(10) 0.077(10) -0.013(7) 0.041(8) -0.031(8) N1 0.052(9) 0.022(7) 0.028(9) -0.007(6) 0.029(8) -0.011(7) C1 0.024(8) 0.047(10) 0.019(9) 0.014(9) 0.015(8) 0.012(9) C2 0.042(10) 0.011(9) 0.050(12) 0.012(7) 0.035(10) 0.010(7) C3 0.058(12) 0.043(10) 0.031(12) -0.014(9) 0.034(11) -0.011(9) C4 0.030(10) 0.050(13) 0.017(10) -0.019(9) 0.013(9) -0.026(10) C5 0.053(12) 0.034(10) 0.026(11) 0.006(8) 0.031(11) 0.004(10) C6 0.032(10) 0.068(13) 0.035(12) -0.002(12) 0.014(9) 0.008(12) C7 0.040(12) 0.069(15) 0.026(12) -0.016(10) 0.015(11) -0.005(10) C8 0.054(11) 0.026(10) 0.046(12) -0.010(10) 0.031(11) -0.003(11) C9 0.049(12) 0.039(11) 0.039(13) 0.001(9) 0.023(11) -0.010(10) C10 0.020(3) 0.019(3) 0.019(3) 0.0005(10) 0.012(2) -0.0004(10) C11 0.030(7) 0.022(7) 0.016(7) 0.005(6) 0.019(6) -0.001(7) _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 Tb1 O2 2.297(9) 7_566 ? Tb1 O1 2.302(8) . ? Tb1 O4 2.348(8) . ? Tb1 O8 2.403(9) 4_546 ? Tb1 O5 2.421(9) 7_566 ? Tb1 O10 2.455(9) 4_546 ? Tb1 O9 2.457(9) . ? Tb1 O7 2.457(8) . ? P1 O1 1.508(9) . ? P1 O2 1.513(9) . ? P1 O3 1.563(9) . ? P1 C1 1.811(14) . ? P2 O4 1.484(9) . ? P2 O5 1.520(9) . ? P2 O6 1.574(9) . ? P2 C2 1.840(13) . ? O2 Tb1 2.297(9) 7_566 ? O3 H3A 0.8388 . ? O5 Tb1 2.421(9) 7_566 ? O6 H6A 0.8357 . ? O7 C10 1.285(14) . ? O8 C10 1.234(15) . ? O8 Tb1 2.403(9) 4_556 ? O9 C11 1.253(15) . ? O10 C11 1.241(15) . ? O10 Tb1 2.455(9) 4_556 ? O1W H1WA 0.8564 . ? O1W H1WB 0.8488 . ? O2W H2WA 0.8516 . ? O2W H2WB 0.8427 . ? N1 C2 1.494(15) . ? N1 C1 1.501(15) . ? N1 C3 1.541(16) . ? N1 H1A 0.9104 . ? C1 H1B 0.9544 . ? C1 H1C 0.9575 . ? C2 H2A 0.9450 . ? C2 H2B 0.9581 . ? C3 C4 1.493(18) . ? C3 H3B 0.9585 . ? C3 H3C 0.9476 . ? C4 C5 1.372(19) . ? C4 C9 1.402(19) . ? C5 C6 1.39(2) . ? C5 H5 0.9300 . ? C6 C7 1.36(2) . ? C6 H6 0.9300 . ? C7 C8 1.382(19) . ? C7 H7 0.9300 . ? C8 C9 1.373(19) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.526(16) . ? 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 O2 Tb1 O1 122.4(3) 7_566 . ? O2 Tb1 O4 77.7(3) 7_566 . ? O1 Tb1 O4 76.4(3) . . ? O2 Tb1 O8 83.5(3) 7_566 4_546 ? O1 Tb1 O8 137.8(3) . 4_546 ? O4 Tb1 O8 145.4(3) . 4_546 ? O2 Tb1 O5 74.1(3) 7_566 7_566 ? O1 Tb1 O5 78.8(3) . 7_566 ? O4 Tb1 O5 123.3(3) . 7_566 ? O8 Tb1 O5 77.6(3) 4_546 7_566 ? O2 Tb1 O10 142.6(3) 7_566 4_546 ? O1 Tb1 O10 75.4(3) . 4_546 ? O4 Tb1 O10 139.5(3) . 4_546 ? O8 Tb1 O10 65.9(3) 4_546 4_546 ? O5 Tb1 O10 78.5(3) 7_566 4_546 ? O2 Tb1 O9 80.0(3) 7_566 . ? O1 Tb1 O9 141.1(3) . . ? O4 Tb1 O9 78.8(3) . . ? O8 Tb1 O9 69.5(3) 4_546 . ? O5 Tb1 O9 140.0(3) 7_566 . ? O10 Tb1 O9 106.8(3) 4_546 . ? O2 Tb1 O7 138.2(3) 7_566 . ? O1 Tb1 O7 78.0(3) . . ? O4 Tb1 O7 72.3(3) . . ? O8 Tb1 O7 105.5(3) 4_546 . ? O5 Tb1 O7 147.4(3) 7_566 . ? O10 Tb1 O7 73.8(3) 4_546 . ? O9 Tb1 O7 66.2(3) . . ? O1 P1 O2 118.2(5) . . ? O1 P1 O3 110.4(5) . . ? O2 P1 O3 111.1(5) . . ? O1 P1 C1 106.1(6) . . ? O2 P1 C1 109.3(6) . . ? O3 P1 C1 100.1(5) . . ? O4 P2 O5 117.4(5) . . ? O4 P2 O6 109.4(5) . . ? O5 P2 O6 110.0(5) . . ? O4 P2 C2 107.9(5) . . ? O5 P2 C2 108.4(6) . . ? O6 P2 C2 102.7(5) . . ? P1 O1 Tb1 142.2(5) . . ? P1 O2 Tb1 146.3(5) . 7_566 ? P1 O3 H3A 108.3 . . ? P2 O4 Tb1 171.5(5) . . ? P2 O5 Tb1 119.5(5) . 7_566 ? P2 O6 H6A 110.7 . . ? C10 O7 Tb1 118.1(8) . . ? C10 O8 Tb1 120.7(9) . 4_556 ? C11 O9 Tb1 119.7(8) . . ? C11 O10 Tb1 119.1(9) . 4_556 ? H1WA O1W H1WB 110.8 . . ? H2WA O2W H2WB 110.1 . . ? C2 N1 C1 114.0(11) . . ? C2 N1 C3 112.5(11) . . ? C1 N1 C3 111.3(10) . . ? C2 N1 H1A 105.4 . . ? C1 N1 H1A 105.2 . . ? C3 N1 H1A 107.7 . . ? N1 C1 P1 115.6(9) . . ? N1 C1 H1B 107.0 . . ? P1 C1 H1B 108.6 . . ? N1 C1 H1C 109.1 . . ? P1 C1 H1C 110.2 . . ? H1B C1 H1C 105.9 . . ? N1 C2 P2 117.7(9) . . ? N1 C2 H2A 107.2 . . ? P2 C2 H2A 106.5 . . ? N1 C2 H2B 107.1 . . ? P2 C2 H2B 110.4 . . ? H2A C2 H2B 107.6 . . ? C4 C3 N1 111.9(12) . . ? C4 C3 H3B 113.4 . . ? N1 C3 H3B 108.4 . . ? C4 C3 H3C 105.4 . . ? N1 C3 H3C 109.3 . . ? H3B C3 H3C 108.3 . . ? C5 C4 C9 117.1(14) . . ? C5 C4 C3 123.3(16) . . ? C9 C4 C3 119.6(15) . . ? C4 C5 C6 123.6(15) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C7 C6 C5 117.8(16) . . ? C7 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? C6 C7 C8 120.6(17) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 120.8(16) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C4 119.9(15) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? O8 C10 O7 124.7(12) . . ? O8 C10 C11 117.5(13) . . ? O7 C10 C11 117.6(12) . . ? O10 C11 O9 127.2(13) . . ? O10 C11 C10 116.1(13) . . ? O9 C11 C10 116.7(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.26 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.188 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.203