# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_szg86 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 N Nd O13 P2' _chemical_formula_weight 516.38 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8190(16) _cell_length_b 9.0047(12) _cell_length_c 14.5674(19) _cell_angle_alpha 90.00 _cell_angle_beta 113.574(2) _cell_angle_gamma 90.00 _cell_volume 1541.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1151 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 21.09 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 3.644 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4615 _exptl_absorpt_correction_T_max 0.8388 _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 8443 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_unetI/netI 0.0844 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3156 _reflns_number_gt 1909 _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^)+(0.0201P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3156 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.007 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 1.09184(3) 0.24685(4) 0.16817(3) 0.01653(11) Uani 1 1 d . . . P1 P 0.82563(15) 0.39225(19) 0.18936(15) 0.0190(4) Uani 1 1 d . . . P2 P 0.61558(16) -0.1027(2) 0.28294(19) 0.0289(5) Uani 1 1 d . . . O1 O 0.8328(4) 0.5550(5) 0.2109(4) 0.0276(13) Uani 1 1 d . . . O2 O 0.9320(3) 0.3097(5) 0.2035(4) 0.0222(12) Uani 1 1 d . . . O3 O 0.7323(4) 0.3711(5) 0.0781(4) 0.0227(12) Uani 1 1 d . . . O4 O 0.7216(4) -0.1938(5) 0.3139(4) 0.0266(13) Uani 1 1 d . . . O5 O 0.5368(4) -0.1354(5) 0.1700(5) 0.0483(18) Uani 1 1 d . . . H5A H 0.5503 -0.2221 0.1545 0.073 Uiso 1 1 d R . . O6 O 0.5513(4) -0.1132(5) 0.3486(5) 0.0417(16) Uani 1 1 d . . . O7 O 1.0464(4) -0.0400(5) -0.0942(4) 0.0210(11) Uani 1 1 d . . . O8 O 1.1352(4) 0.0783(5) 0.0514(4) 0.0234(12) Uani 1 1 d . . . O9 O 0.9128(4) 0.4850(5) -0.1268(4) 0.0261(13) Uani 1 1 d . . . O10 O 0.9655(4) 0.3126(5) -0.0075(4) 0.0298(13) Uani 1 1 d . . . O11 O 1.1747(3) 0.3928(5) 0.3249(4) 0.0244(12) Uani 1 1 d . . . H11A H 1.1217 0.4366 0.3353 0.037 Uiso 1 1 d R . . H11B H 1.2100 0.3350 0.3736 0.037 Uiso 1 1 d R . . O1W O 0.3283(4) 0.3375(6) 0.5079(4) 0.0519(17) Uani 1 1 d . . . H1WA H 0.2957 0.3988 0.5322 0.078 Uiso 1 1 d R . . H1WB H 0.3404 0.2565 0.5405 0.078 Uiso 1 1 d R . . O2W O 0.5545(4) 0.6124(5) 0.0936(5) 0.0511(18) Uani 1 1 d . . . H2WC H 0.5038 0.5468 0.0848 0.061 Uiso 1 1 d R . . N1 N 0.7114(5) 0.1526(5) 0.2257(5) 0.0217(15) Uani 1 1 d . . . H1A H 0.7708 0.0904 0.2351 0.026 Uiso 1 1 d R . . C1 C 0.7593(5) 0.3038(6) 0.2641(6) 0.0205(17) Uani 1 1 d . . . H1B H 0.8146 0.2944 0.3317 0.025 Uiso 1 1 d R . . H1C H 0.6990 0.3662 0.2651 0.025 Uiso 1 1 d R . . C2 C 0.6498(6) 0.0950(7) 0.2865(7) 0.034(2) Uani 1 1 d . . . H2A H 0.5796 0.1490 0.2664 0.041 Uiso 1 1 d R . . H2B H 0.6944 0.1205 0.3551 0.041 Uiso 1 1 d R . . C3 C 0.6360(6) 0.1560(8) 0.1139(6) 0.029(2) Uani 1 1 d . . . H3A H 0.6102 0.0572 0.0915 0.034 Uiso 1 1 d R . . H3B H 0.5702 0.2161 0.1030 0.034 Uiso 1 1 d R . . C4 C 0.6973(6) 0.2165(7) 0.0541(6) 0.0292(19) Uani 1 1 d . . . H4B H 0.7634 0.1568 0.0659 0.035 Uiso 1 1 d R . . H4A H 0.6486 0.2093 -0.0157 0.035 Uiso 1 1 d R . . C5 C 1.0524(5) 0.0123(7) -0.0129(6) 0.0188(17) Uani 1 1 d . . . C6 C 0.9648(6) 0.4410(7) -0.0389(6) 0.0229(18) Uani 1 1 d . . . H2WB H 0.6118 0.5588 0.0999 0.027 Uiso 1 1 d R . . 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 0.01789(17) 0.01257(16) 0.01830(19) -0.0002(2) 0.00635(14) -0.00052(19) P1 0.0187(10) 0.0159(9) 0.0205(12) -0.0009(9) 0.0058(9) -0.0011(7) P2 0.0216(10) 0.0234(10) 0.0452(16) 0.0099(11) 0.0170(11) 0.0021(8) O1 0.042(3) 0.015(2) 0.027(3) -0.003(2) 0.015(3) 0.000(2) O2 0.018(2) 0.022(2) 0.027(3) -0.003(2) 0.010(2) -0.0022(19) O3 0.028(3) 0.017(2) 0.019(3) 0.000(2) 0.005(2) -0.003(2) O4 0.025(3) 0.022(2) 0.035(3) 0.005(2) 0.014(3) -0.001(2) O5 0.039(3) 0.031(3) 0.050(4) 0.009(3) -0.008(3) 0.001(3) O6 0.039(3) 0.029(3) 0.073(5) 0.012(3) 0.040(3) 0.003(2) O7 0.028(3) 0.020(3) 0.020(3) -0.007(2) 0.015(3) -0.005(2) O8 0.020(3) 0.029(3) 0.021(3) -0.008(2) 0.009(2) -0.005(2) O9 0.030(3) 0.018(3) 0.019(3) 0.003(2) -0.003(3) -0.002(2) O10 0.041(3) 0.015(2) 0.024(3) 0.006(2) 0.003(3) -0.005(2) O11 0.027(3) 0.022(3) 0.024(3) 0.002(2) 0.010(3) 0.006(2) O1W 0.043(4) 0.070(4) 0.046(4) 0.019(3) 0.020(4) 0.016(3) O2W 0.050(4) 0.034(3) 0.074(5) -0.005(3) 0.030(4) 0.006(3) N1 0.024(3) 0.014(3) 0.030(4) 0.001(3) 0.015(3) 0.005(2) C1 0.018(4) 0.014(3) 0.028(5) -0.004(3) 0.009(4) 0.001(3) C2 0.036(5) 0.029(4) 0.048(6) 0.007(4) 0.029(5) 0.005(3) C3 0.020(4) 0.029(4) 0.032(5) -0.005(4) 0.005(4) -0.001(3) C4 0.031(4) 0.030(5) 0.022(4) -0.003(4) 0.007(4) -0.002(3) C5 0.023(4) 0.010(3) 0.027(5) 0.006(3) 0.014(4) 0.004(3) C6 0.022(4) 0.020(4) 0.023(5) 0.004(4) 0.005(4) 0.002(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 O4 2.361(4) 2_755 ? Nd1 O2 2.373(4) . ? Nd1 O1 2.379(5) 2_745 ? Nd1 O11 2.476(5) . ? Nd1 O9 2.484(4) 3_765 ? Nd1 O10 2.492(5) . ? Nd1 O7 2.499(4) 3_755 ? Nd1 O8 2.502(5) . ? P1 O2 1.493(4) . ? P1 O1 1.494(4) . ? P1 O3 1.595(5) . ? P1 C1 1.811(7) . ? P2 O4 1.494(5) . ? P2 O6 1.495(6) . ? P2 O5 1.576(6) . ? P2 C2 1.830(7) . ? O1 Nd1 2.379(5) 2_755 ? O3 C4 1.462(7) . ? O4 Nd1 2.361(4) 2_745 ? O5 H5A 0.8500 . ? O7 C5 1.248(9) . ? O7 Nd1 2.499(4) 3_755 ? O8 C5 1.250(8) . ? O9 C6 1.249(8) . ? O9 Nd1 2.484(4) 3_765 ? O10 C6 1.242(7) . ? O11 H11A 0.8500 . ? O11 H11B 0.8500 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WC 0.8500 . ? O2W H2WB 0.8527 . ? N1 C2 1.496(9) . ? N1 C1 1.507(7) . ? N1 C3 1.525(9) . ? N1 H1A 0.9100 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C3 C4 1.490(10) . ? C3 H3A 0.9599 . ? C3 H3B 0.9600 . ? C4 H4B 0.9599 . ? C4 H4A 0.9600 . ? C5 C5 1.548(13) 3_755 ? C6 C6 1.552(13) 3_765 ? 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 O4 Nd1 O2 147.84(15) 2_755 . ? O4 Nd1 O1 89.38(16) 2_755 2_745 ? O2 Nd1 O1 98.20(16) . 2_745 ? O4 Nd1 O11 74.65(16) 2_755 . ? O2 Nd1 O11 76.27(15) . . ? O1 Nd1 O11 78.78(16) 2_745 . ? O4 Nd1 O9 74.44(15) 2_755 3_765 ? O2 Nd1 O9 83.19(16) . 3_765 ? O1 Nd1 O9 148.09(16) 2_745 3_765 ? O11 Nd1 O9 70.56(15) . 3_765 ? O4 Nd1 O10 105.89(17) 2_755 . ? O2 Nd1 O10 84.43(17) . . ? O1 Nd1 O10 146.90(15) 2_745 . ? O11 Nd1 O10 133.16(15) . . ? O9 Nd1 O10 64.99(15) 3_765 . ? O4 Nd1 O7 136.79(15) 2_755 3_755 ? O2 Nd1 O7 75.30(14) . 3_755 ? O1 Nd1 O7 77.64(15) 2_745 3_755 ? O11 Nd1 O7 139.68(16) . 3_755 ? O9 Nd1 O7 132.53(15) 3_765 3_755 ? O10 Nd1 O7 71.12(15) . 3_755 ? O4 Nd1 O8 73.86(15) 2_755 . ? O2 Nd1 O8 137.58(14) . . ? O1 Nd1 O8 85.86(16) 2_745 . ? O11 Nd1 O8 144.95(14) . . ? O9 Nd1 O8 114.54(16) 3_765 . ? O10 Nd1 O8 71.10(16) . . ? O7 Nd1 O8 64.33(14) 3_755 . ? O2 P1 O1 118.9(3) . . ? O2 P1 O3 110.7(3) . . ? O1 P1 O3 106.8(3) . . ? O2 P1 C1 108.7(3) . . ? O1 P1 C1 108.0(3) . . ? O3 P1 C1 102.5(3) . . ? O4 P2 O6 116.1(3) . . ? O4 P2 O5 109.8(3) . . ? O6 P2 O5 111.7(3) . . ? O4 P2 C2 110.3(3) . . ? O6 P2 C2 103.3(3) . . ? O5 P2 C2 104.9(3) . . ? P1 O1 Nd1 147.2(3) . 2_755 ? P1 O2 Nd1 155.4(3) . . ? C4 O3 P1 113.0(4) . . ? P2 O4 Nd1 156.4(3) . 2_745 ? P2 O5 H5A 109.6 . . ? C5 O7 Nd1 117.0(4) . 3_755 ? C5 O8 Nd1 116.4(4) . . ? C6 O9 Nd1 120.6(4) . 3_765 ? C6 O10 Nd1 120.3(4) . . ? Nd1 O11 H11A 109.4 . . ? Nd1 O11 H11B 109.4 . . ? H11A O11 H11B 109.5 . . ? H1WA O1W H1WB 109.6 . . ? H2WC O2W H2WB 101.3 . . ? C2 N1 C1 109.0(6) . . ? C2 N1 C3 112.3(5) . . ? C1 N1 C3 111.6(5) . . ? C2 N1 H1A 107.8 . . ? C1 N1 H1A 107.9 . . ? C3 N1 H1A 108.0 . . ? N1 C1 P1 113.2(5) . . ? N1 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? N1 C1 H1C 108.9 . . ? P1 C1 H1C 109.0 . . ? H1B C1 H1C 107.8 . . ? N1 C2 P2 119.9(5) . . ? N1 C2 H2A 107.3 . . ? P2 C2 H2A 107.4 . . ? N1 C2 H2B 107.4 . . ? P2 C2 H2B 107.4 . . ? H2A C2 H2B 106.9 . . ? C4 C3 N1 111.9(5) . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3A 109.3 . . ? C4 C3 H3B 109.2 . . ? N1 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O3 C4 C3 113.1(6) . . ? O3 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? O3 C4 H4A 109.0 . . ? C3 C4 H4A 108.9 . . ? H4B C4 H4A 107.8 . . ? O7 C5 O8 127.0(6) . . ? O7 C5 C5 116.5(8) . 3_755 ? O8 C5 C5 116.4(9) . 3_755 ? O10 C6 O9 126.5(6) . . ? O10 C6 C6 116.9(8) . 3_765 ? O9 C6 C6 116.6(7) . 3_765 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.738 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.185 _database_code_depnum_ccdc_archive 'CCDC 670986' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_szg85 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 N O13 P2 Sm' _chemical_formula_weight 522.49 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7908(13) _cell_length_b 8.9552(9) _cell_length_c 14.5187(15) _cell_angle_alpha 90.00 _cell_angle_beta 113.4860(10) _cell_angle_gamma 90.00 _cell_volume 1525.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3857 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.72 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 4.128 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4042 _exptl_absorpt_correction_T_max 0.8425 _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 'CCD area detector' _diffrn_measurement_method 'phi and 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 8242 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_unetI/netI 0.0328 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3151 _reflns_number_gt 2594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0233P)^2^+1.6159P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3151 _refine_ls_number_parameters 208 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.127 _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 1.091003(15) 0.24723(2) 0.166965(14) 0.01445(8) Uani 1 1 d . . . P1 P 0.82776(8) 0.39458(11) 0.18975(7) 0.0177(2) Uani 1 1 d . . . P2 P 0.61752(9) -0.10394(13) 0.28390(9) 0.0260(2) Uani 1 1 d . . . O1 O 0.8357(2) 0.5575(3) 0.2120(2) 0.0254(6) Uani 1 1 d . . . O2 O 0.9331(2) 0.3107(3) 0.2029(2) 0.0253(6) Uani 1 1 d . . . O3 O 0.7338(2) 0.3745(3) 0.0784(2) 0.0247(6) Uani 1 1 d . . . O4 O 0.7243(2) -0.1951(3) 0.3150(2) 0.0268(7) Uani 1 1 d . . . O5 O 0.5394(3) -0.1364(4) 0.1711(3) 0.0445(9) Uani 1 1 d . . . H5A H 0.5528 -0.2231 0.1556 0.067 Uiso 1 1 d R . . O6 O 0.5526(3) -0.1147(4) 0.3492(3) 0.0421(9) Uani 1 1 d . . . O7 O 1.0463(2) -0.0406(3) -0.09471(19) 0.0218(6) Uani 1 1 d . . . O8 O 1.1355(2) 0.0788(3) 0.0518(2) 0.0255(6) Uani 1 1 d . . . O9 O 0.9123(2) 0.4863(3) -0.1274(2) 0.0259(6) Uani 1 1 d . . . O10 O 0.9659(3) 0.3112(3) -0.0077(2) 0.0298(7) Uani 1 1 d . . . O11 O 1.1734(2) 0.3925(3) 0.32282(19) 0.0230(6) Uani 1 1 d D . . H11A H 1.1204 0.4363 0.3332 0.034 Uiso 1 1 d RD . . H11B H 1.2087 0.3346 0.3715 0.034 Uiso 1 1 d RD . . O1W O 0.3278(3) 0.3392(4) 0.5077(2) 0.0481(9) Uani 1 1 d . . . H1WA H 0.2952 0.4005 0.5320 0.072 Uiso 1 1 d RD . . H1WB H 0.3399 0.2583 0.5403 0.072 Uiso 1 1 d RD . . O2W O 0.5539(3) 0.6109(4) 0.0935(3) 0.0506(10) Uani 1 1 d . . . H2WC H 0.5032 0.5452 0.0846 0.061 Uiso 1 1 d R . . N1 N 0.7130(3) 0.1523(4) 0.2263(2) 0.0198(7) Uani 1 1 d . . . H1A H 0.7724 0.0902 0.2357 0.024 Uiso 1 1 d R . . C1 C 0.7600(3) 0.3050(5) 0.2644(3) 0.0205(8) Uani 1 1 d . . . H1B H 0.8153 0.2956 0.3320 0.025 Uiso 1 1 d R . . H1C H 0.6997 0.3674 0.2654 0.025 Uiso 1 1 d R . . C2 C 0.6507(4) 0.0942(5) 0.2869(3) 0.0274(10) Uani 1 1 d . . . H2A H 0.5804 0.1482 0.2667 0.033 Uiso 1 1 d R . . H2B H 0.6952 0.1198 0.3555 0.033 Uiso 1 1 d R . . C3 C 0.6375(3) 0.1577(5) 0.1150(3) 0.0278(10) Uani 1 1 d . . . H3A H 0.6118 0.0589 0.0925 0.033 Uiso 1 1 d R . . H3B H 0.5717 0.2179 0.1040 0.033 Uiso 1 1 d R . . C4 C 0.6990(4) 0.2191(5) 0.0530(3) 0.0284(10) Uani 1 1 d . . . H4B H 0.7652 0.1594 0.0648 0.034 Uiso 1 1 d R . . H4A H 0.6503 0.2120 -0.0168 0.034 Uiso 1 1 d R . . C5 C 1.0532(3) 0.0116(4) -0.0119(3) 0.0172(8) Uani 1 1 d . . . C6 C 0.9647(3) 0.4412(4) -0.0391(3) 0.0213(9) Uani 1 1 d . . . H2WB H 0.6117 0.5591 0.0996 0.026 Uiso 1 1 d R . . 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 0.01644(12) 0.01072(11) 0.01615(12) -0.00018(7) 0.00644(9) -0.00042(7) P1 0.0180(5) 0.0138(5) 0.0209(5) -0.0024(4) 0.0074(4) -0.0012(4) P2 0.0208(5) 0.0199(6) 0.0408(7) 0.0076(5) 0.0160(5) 0.0014(4) O1 0.0335(16) 0.0159(15) 0.0271(16) -0.0043(12) 0.0124(14) -0.0030(12) O2 0.0191(14) 0.0261(16) 0.0307(17) -0.0037(13) 0.0100(13) 0.0013(12) O3 0.0242(15) 0.0230(16) 0.0222(15) 0.0011(12) 0.0042(12) -0.0003(12) O4 0.0224(15) 0.0226(16) 0.0379(18) 0.0079(13) 0.0146(14) 0.0044(12) O5 0.0344(18) 0.033(2) 0.047(2) 0.0048(16) -0.0032(16) -0.0032(15) O6 0.0404(19) 0.031(2) 0.073(2) 0.0152(17) 0.0426(19) 0.0074(15) O7 0.0255(15) 0.0214(16) 0.0218(15) -0.0066(11) 0.0131(12) -0.0059(12) O8 0.0217(15) 0.0286(17) 0.0279(16) -0.0116(12) 0.0116(13) -0.0063(12) O9 0.0305(16) 0.0171(16) 0.0209(15) 0.0029(12) 0.0006(13) -0.0013(12) O10 0.0414(18) 0.0128(15) 0.0252(16) 0.0032(12) 0.0029(14) -0.0049(13) O11 0.0229(14) 0.0263(17) 0.0181(14) -0.0013(12) 0.0066(12) 0.0039(12) O1W 0.044(2) 0.065(3) 0.039(2) 0.0151(18) 0.0199(18) 0.0125(18) O2W 0.047(2) 0.039(2) 0.069(3) -0.0063(19) 0.027(2) 0.0020(17) N1 0.0163(16) 0.0143(17) 0.0303(19) 0.0018(14) 0.0109(15) 0.0009(12) C1 0.023(2) 0.014(2) 0.026(2) -0.0017(16) 0.0109(18) -0.0018(16) C2 0.031(2) 0.021(2) 0.040(3) 0.0050(18) 0.024(2) 0.0040(17) C3 0.021(2) 0.022(2) 0.034(3) -0.0021(18) 0.0043(19) -0.0007(17) C4 0.031(2) 0.022(2) 0.029(2) -0.0040(17) 0.008(2) -0.0046(17) C5 0.018(2) 0.010(2) 0.024(2) 0.0007(15) 0.0093(17) 0.0009(14) C6 0.020(2) 0.017(2) 0.025(2) -0.0005(17) 0.0060(18) -0.0007(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 Sm1 O4 2.329(3) 2_755 ? Sm1 O2 2.348(3) . ? Sm1 O1 2.354(3) 2_745 ? Sm1 O9 2.451(3) 3_765 ? Sm1 O11 2.454(3) . ? Sm1 O10 2.467(3) . ? Sm1 O7 2.478(3) 3_755 ? Sm1 O8 2.481(3) . ? P1 O2 1.487(3) . ? P1 O1 1.489(3) . ? P1 O3 1.594(3) . ? P1 C1 1.822(4) . ? P2 O6 1.492(3) . ? P2 O4 1.498(3) . ? P2 O5 1.569(3) . ? P2 C2 1.821(4) . ? O1 Sm1 2.354(3) 2_755 ? O3 C4 1.462(5) . ? O4 Sm1 2.329(3) 2_745 ? O5 H5A 0.8456 . ? O7 C5 1.260(4) . ? O7 Sm1 2.478(3) 3_755 ? O8 C5 1.245(4) . ? O9 C6 1.253(5) . ? O9 Sm1 2.451(3) 3_765 ? O10 C6 1.248(5) . ? O11 H11A 0.8473 . ? O11 H11B 0.8471 . ? O1W H1WA 0.8465 . ? O1W H1WB 0.8459 . ? O2W H2WC 0.8469 . ? O2W H2WB 0.8471 . ? N1 C2 1.496(5) . ? N1 C1 1.508(5) . ? N1 C3 1.518(5) . ? N1 H1A 0.9071 . ? C1 H1B 0.9581 . ? C1 H1C 0.9568 . ? C2 H2A 0.9575 . ? C2 H2B 0.9576 . ? C3 C4 1.515(6) . ? C3 H3A 0.9552 . ? C3 H3B 0.9571 . ? C4 H4B 0.9570 . ? C4 H4A 0.9579 . ? C5 C5 1.546(7) 3_755 ? C6 C6 1.549(8) 3_765 ? 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 O4 Sm1 O2 147.68(10) 2_755 . ? O4 Sm1 O1 89.54(10) 2_755 2_745 ? O2 Sm1 O1 97.51(10) . 2_745 ? O4 Sm1 O9 74.48(10) 2_755 3_765 ? O2 Sm1 O9 83.12(10) . 3_765 ? O1 Sm1 O9 147.40(10) 2_745 3_765 ? O4 Sm1 O11 74.63(9) 2_755 . ? O2 Sm1 O11 76.01(9) . . ? O1 Sm1 O11 78.30(9) 2_745 . ? O9 Sm1 O11 70.19(9) 3_765 . ? O4 Sm1 O10 106.09(10) 2_755 . ? O2 Sm1 O10 84.80(10) . . ? O1 Sm1 O10 146.85(10) 2_745 . ? O9 Sm1 O10 65.75(9) 3_765 . ? O11 Sm1 O10 133.56(10) . . ? O4 Sm1 O7 136.83(9) 2_755 3_755 ? O2 Sm1 O7 75.38(9) . 3_755 ? O1 Sm1 O7 77.36(9) 2_745 3_755 ? O9 Sm1 O7 133.20(9) 3_765 3_755 ? O11 Sm1 O7 139.26(8) . 3_755 ? O10 Sm1 O7 71.24(9) . 3_755 ? O4 Sm1 O8 73.48(9) 2_755 . ? O2 Sm1 O8 138.22(9) . . ? O1 Sm1 O8 86.23(10) 2_745 . ? O9 Sm1 O8 114.90(10) 3_765 . ? O11 Sm1 O8 144.51(9) . . ? O10 Sm1 O8 71.17(10) . . ? O7 Sm1 O8 64.85(8) 3_755 . ? O2 P1 O1 119.12(17) . . ? O2 P1 O3 110.61(16) . . ? O1 P1 O3 106.81(16) . . ? O2 P1 C1 108.86(18) . . ? O1 P1 C1 108.06(17) . . ? O3 P1 C1 102.00(17) . . ? O6 P2 O4 116.44(18) . . ? O6 P2 O5 111.5(2) . . ? O4 P2 O5 109.81(19) . . ? O6 P2 C2 103.36(19) . . ? O4 P2 C2 110.38(18) . . ? O5 P2 C2 104.5(2) . . ? P1 O1 Sm1 147.33(18) . 2_755 ? P1 O2 Sm1 155.43(19) . . ? C4 O3 P1 113.2(2) . . ? P2 O4 Sm1 156.48(18) . 2_745 ? P2 O5 H5A 109.6 . . ? C5 O7 Sm1 116.7(2) . 3_755 ? C5 O8 Sm1 116.2(2) . . ? C6 O9 Sm1 120.4(2) . 3_765 ? C6 O10 Sm1 120.1(3) . . ? Sm1 O11 H11A 109.2 . . ? Sm1 O11 H11B 109.6 . . ? H11A O11 H11B 109.5 . . ? H1WA O1W H1WB 109.5 . . ? H2WC O2W H2WB 102.7 . . ? C2 N1 C1 109.1(3) . . ? C2 N1 C3 112.0(3) . . ? C1 N1 C3 110.7(3) . . ? C2 N1 H1A 108.0 . . ? C1 N1 H1A 108.3 . . ? C3 N1 H1A 108.6 . . ? N1 C1 P1 113.3(3) . . ? N1 C1 H1B 108.6 . . ? P1 C1 H1B 108.4 . . ? N1 C1 H1C 109.2 . . ? P1 C1 H1C 109.2 . . ? H1B C1 H1C 107.9 . . ? N1 C2 P2 119.9(3) . . ? N1 C2 H2A 107.5 . . ? P2 C2 H2A 107.7 . . ? N1 C2 H2B 107.0 . . ? P2 C2 H2B 107.1 . . ? H2A C2 H2B 107.1 . . ? C4 C3 N1 112.5(3) . . ? C4 C3 H3A 108.9 . . ? N1 C3 H3A 108.7 . . ? C4 C3 H3B 109.1 . . ? N1 C3 H3B 109.8 . . ? H3A C3 H3B 107.7 . . ? O3 C4 C3 111.9(3) . . ? O3 C4 H4B 109.2 . . ? C3 C4 H4B 108.8 . . ? O3 C4 H4A 109.6 . . ? C3 C4 H4A 109.4 . . ? H4B C4 H4A 107.9 . . ? O8 C5 O7 127.2(3) . . ? O8 C5 C5 117.2(4) . 3_755 ? O7 C5 C5 115.5(4) . 3_755 ? O10 C6 O9 126.7(4) . . ? O10 C6 C6 116.6(4) . 3_765 ? O9 C6 C6 116.7(4) . 3_765 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O11 0.91 2.19 2.977(4) 144.3 2_745 O5 H5A O2W 0.85 1.74 2.568(5) 165.2 1_545 O11 H11A O7 0.85 1.91 2.718(4) 158.4 4_566 N1 H1A O9 0.91 2.19 2.870(4) 131.4 4_566 O1W H1WA O8 0.85 2.18 2.873(4) 138.9 4_466 O1W H1WB O6 0.85 2.09 2.858(5) 151.1 3_656 O1W H1WB O4 0.85 2.60 3.179(4) 126.3 3_656 O2W H2WC O6 0.85 2.01 2.745(5) 145.1 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.644 _refine_diff_density_min -0.629 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 670985' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_szg114 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Eu N O13 P2' _chemical_formula_weight 524.10 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7935(18) _cell_length_b 8.9211(12) _cell_length_c 14.501(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.489(2) _cell_angle_gamma 90.00 _cell_volume 1517.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1657 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 26.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 4.412 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4174 _exptl_absorpt_correction_T_max 0.8433 _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 8258 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0595 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3137 _reflns_number_gt 2065 _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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3137 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 1.09068(2) 0.24728(3) 0.16643(2) 0.01609(10) Uani 1 1 d . . . P1 P 0.82870(14) 0.39523(17) 0.18985(12) 0.0194(4) Uani 1 1 d . . . P2 P 0.61851(15) -0.10474(19) 0.28385(14) 0.0283(4) Uani 1 1 d . . . O1 O 0.8380(4) 0.5584(4) 0.2132(3) 0.0246(10) Uani 1 1 d . . . O2 O 0.9341(3) 0.3105(5) 0.2026(3) 0.0254(10) Uani 1 1 d . . . O3 O 0.7356(3) 0.3761(5) 0.0790(3) 0.0257(10) Uani 1 1 d . . . O4 O 0.7255(4) -0.1954(5) 0.3150(3) 0.0275(11) Uani 1 1 d . . . O5 O 0.5404(4) -0.1371(6) 0.1713(4) 0.0460(14) Uani 1 1 d . . . H5A H 0.5538 -0.2239 0.1558 0.069 Uiso 1 1 d R . . O6 O 0.5539(4) -0.1163(5) 0.3496(4) 0.0429(13) Uani 1 1 d . . . O7 O 1.0463(4) -0.0416(4) -0.0946(3) 0.0217(10) Uani 1 1 d . . . O8 O 1.1359(3) 0.0793(5) 0.0519(3) 0.0264(11) Uani 1 1 d . . . O9 O 0.9122(4) 0.4865(5) -0.1272(3) 0.0285(11) Uani 1 1 d . . . O10 O 0.9659(4) 0.3104(5) -0.0075(3) 0.0289(11) Uani 1 1 d . . . O11 O 1.1722(3) 0.3920(5) 0.3218(3) 0.0240(10) Uani 1 1 d . . . H11A H 1.1192 0.4358 0.3322 0.036 Uiso 1 1 d R . . H11B H 1.2076 0.3341 0.3705 0.036 Uiso 1 1 d R . . O1W O 0.3278(4) 0.3392(6) 0.5073(3) 0.0498(15) Uani 1 1 d . . . H1WA H 0.2952 0.4005 0.5315 0.075 Uiso 1 1 d R . . H1WB H 0.3399 0.2582 0.5399 0.075 Uiso 1 1 d R . . O2W O 0.5548(4) 0.6091(6) 0.0938(4) 0.0509(15) Uani 1 1 d . . . H2WC H 0.5041 0.5434 0.0850 0.061 Uiso 1 1 d R . . N1 N 0.7139(4) 0.1529(5) 0.2265(4) 0.0205(12) Uani 1 1 d . . . H1A H 0.7733 0.0908 0.2359 0.025 Uiso 1 1 d R . . C1 C 0.7613(5) 0.3058(7) 0.2640(5) 0.0221(14) Uani 1 1 d . . . H1B H 0.8166 0.2963 0.3316 0.027 Uiso 1 1 d R . . H1C H 0.7010 0.3682 0.2649 0.027 Uiso 1 1 d R . . C2 C 0.6508(6) 0.0952(7) 0.2867(5) 0.0323(17) Uani 1 1 d . . . H2A H 0.5805 0.1492 0.2666 0.039 Uiso 1 1 d R . . H2B H 0.6953 0.1208 0.3554 0.039 Uiso 1 1 d R . . C3 C 0.6376(5) 0.1600(7) 0.1156(5) 0.0279(16) Uani 1 1 d . . . H3A H 0.6119 0.0611 0.0932 0.034 Uiso 1 1 d R . . H3B H 0.5718 0.2201 0.1046 0.034 Uiso 1 1 d R . . C4 C 0.6994(6) 0.2202(7) 0.0525(5) 0.0292(16) Uani 1 1 d . . . H4B H 0.7656 0.1605 0.0643 0.035 Uiso 1 1 d R . . H4A H 0.6507 0.2130 -0.0174 0.035 Uiso 1 1 d R . . C5 C 1.0538(5) 0.0122(7) -0.0118(5) 0.0221(15) Uani 1 1 d . . . C6 C 0.9650(5) 0.4414(6) -0.0388(5) 0.0213(14) Uani 1 1 d . . . H2WB H 0.6121 0.5592 0.1000 0.026 Uiso 1 1 d R . . 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 0.01951(16) 0.00994(14) 0.01871(17) -0.00008(14) 0.00751(12) -0.00046(15) P1 0.0223(9) 0.0122(8) 0.0244(10) -0.0009(7) 0.0101(8) -0.0005(7) P2 0.0257(10) 0.0188(9) 0.0440(12) 0.0076(8) 0.0179(9) 0.0016(7) O1 0.035(3) 0.014(2) 0.023(3) -0.0030(18) 0.010(2) -0.0006(19) O2 0.021(2) 0.020(2) 0.035(3) -0.004(2) 0.011(2) 0.0010(19) O3 0.030(3) 0.018(2) 0.024(3) -0.0002(19) 0.005(2) -0.004(2) O4 0.026(2) 0.021(2) 0.038(3) 0.005(2) 0.015(2) 0.0038(19) O5 0.035(3) 0.033(3) 0.051(4) 0.007(3) -0.003(3) -0.002(2) O6 0.044(3) 0.033(3) 0.068(4) 0.013(3) 0.041(3) 0.007(2) O7 0.029(2) 0.019(2) 0.022(3) -0.0040(18) 0.016(2) -0.002(2) O8 0.023(2) 0.029(3) 0.028(3) -0.010(2) 0.011(2) -0.007(2) O9 0.033(3) 0.020(2) 0.022(3) 0.004(2) 0.001(2) -0.003(2) O10 0.043(3) 0.011(2) 0.023(3) 0.0038(19) 0.002(2) -0.004(2) O11 0.027(2) 0.022(2) 0.022(2) -0.0004(19) 0.008(2) 0.0040(19) O1W 0.049(3) 0.067(4) 0.037(3) 0.015(3) 0.021(3) 0.014(3) O2W 0.044(3) 0.040(3) 0.072(4) -0.005(3) 0.026(3) 0.005(3) N1 0.018(3) 0.016(3) 0.027(3) 0.002(2) 0.009(2) 0.004(2) C1 0.026(4) 0.017(3) 0.024(4) -0.002(3) 0.011(3) 0.003(3) C2 0.033(4) 0.026(4) 0.051(5) 0.004(3) 0.031(4) 0.001(3) C3 0.018(4) 0.024(4) 0.033(4) -0.002(3) 0.001(3) -0.003(3) C4 0.031(4) 0.025(4) 0.025(4) -0.006(3) 0.004(3) -0.008(3) C5 0.025(4) 0.009(3) 0.033(4) 0.004(3) 0.013(3) 0.004(3) C6 0.027(4) 0.012(3) 0.021(4) 0.002(3) 0.007(3) 0.001(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 Eu1 O4 2.315(4) 2_755 ? Eu1 O1 2.335(4) 2_745 ? Eu1 O2 2.333(4) . ? Eu1 O11 2.441(4) . ? Eu1 O9 2.439(4) 3_765 ? Eu1 O7 2.463(4) 3_755 ? Eu1 O10 2.453(4) . ? Eu1 O8 2.471(4) . ? Eu1 C5 3.214(6) . ? Eu1 C5 3.241(6) 3_755 ? P1 O1 1.488(4) . ? P1 O2 1.492(4) . ? P1 O3 1.583(4) . ? P1 C1 1.809(6) . ? P2 O4 1.497(4) . ? P2 O6 1.493(5) . ? P2 O5 1.564(5) . ? P2 C2 1.828(6) . ? O1 Eu1 2.335(4) 2_755 ? O3 C4 1.467(7) . ? O4 Eu1 2.315(4) 2_745 ? O5 H5A 0.8428 . ? O7 C5 1.261(7) . ? O7 Eu1 2.463(4) 3_755 ? O8 C5 1.241(7) . ? O9 C6 1.255(7) . ? O9 Eu1 2.439(4) 3_765 ? O10 C6 1.252(7) . ? O11 H11A 0.8467 . ? O11 H11B 0.8454 . ? O1W H1WA 0.8449 . ? O1W H1WB 0.8433 . ? O2W H2WC 0.8455 . ? O2W H2WB 0.8307 . ? N1 C2 1.497(7) . ? N1 C1 1.504(7) . ? N1 C3 1.514(7) . ? N1 H1A 0.9059 . ? C1 H1B 0.9572 . ? C1 H1C 0.9557 . ? C2 H2A 0.9567 . ? C2 H2B 0.9565 . ? C3 C4 1.526(8) . ? C3 H3A 0.9520 . ? C3 H3B 0.9562 . ? C4 H4B 0.9561 . ? C4 H4A 0.9569 . ? C5 C5 1.561(12) 3_755 ? C5 Eu1 3.241(6) 3_755 ? C6 C6 1.535(11) 3_765 ? 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 O4 Eu1 O1 89.79(15) 2_755 2_745 ? O4 Eu1 O2 147.54(15) 2_755 . ? O1 Eu1 O2 96.96(15) 2_745 . ? O4 Eu1 O11 74.63(14) 2_755 . ? O1 Eu1 O11 78.21(14) 2_745 . ? O2 Eu1 O11 75.77(14) . . ? O4 Eu1 O9 74.47(15) 2_755 3_765 ? O1 Eu1 O9 147.38(14) 2_745 3_765 ? O2 Eu1 O9 83.24(15) . 3_765 ? O11 Eu1 O9 70.20(14) . 3_765 ? O4 Eu1 O7 137.08(14) 2_755 3_755 ? O1 Eu1 O7 77.20(14) 2_745 3_755 ? O2 Eu1 O7 75.25(14) . 3_755 ? O11 Eu1 O7 138.99(13) . 3_755 ? O9 Eu1 O7 133.22(13) 3_765 3_755 ? O4 Eu1 O10 106.47(15) 2_755 . ? O1 Eu1 O10 146.59(14) 2_745 . ? O2 Eu1 O10 84.86(15) . . ? O11 Eu1 O10 133.73(14) . . ? O9 Eu1 O10 66.02(14) 3_765 . ? O7 Eu1 O10 71.01(14) 3_755 . ? O4 Eu1 O8 73.34(14) 2_755 . ? O1 Eu1 O8 86.48(14) 2_745 . ? O2 Eu1 O8 138.56(14) . . ? O11 Eu1 O8 144.38(13) . . ? O9 Eu1 O8 114.82(15) 3_765 . ? O7 Eu1 O8 65.27(13) 3_755 . ? O10 Eu1 O8 71.26(15) . . ? O4 Eu1 C5 93.12(15) 2_755 . ? O1 Eu1 C5 91.07(14) 2_745 . ? O2 Eu1 C5 118.33(15) . . ? O11 Eu1 C5 163.57(14) . . ? O9 Eu1 C5 117.66(15) 3_765 . ? O7 Eu1 C5 47.33(14) 3_755 . ? O10 Eu1 C5 59.75(15) . . ? O8 Eu1 C5 20.32(13) . . ? O4 Eu1 C5 120.75(15) 2_755 3_755 ? O1 Eu1 C5 86.96(15) 2_745 3_755 ? O2 Eu1 C5 91.38(15) . 3_755 ? O11 Eu1 C5 158.86(15) . 3_755 ? O9 Eu1 C5 125.65(15) 3_765 3_755 ? O7 Eu1 C5 20.24(14) 3_755 3_755 ? O10 Eu1 C5 59.63(15) . 3_755 ? O8 Eu1 C5 47.42(14) . 3_755 ? C5 Eu1 C5 28.0(2) . 3_755 ? O1 P1 O2 118.7(3) . . ? O1 P1 O3 107.2(2) . . ? O2 P1 O3 110.4(2) . . ? O1 P1 C1 108.1(3) . . ? O2 P1 C1 108.9(3) . . ? O3 P1 C1 102.2(3) . . ? O4 P2 O6 116.3(3) . . ? O4 P2 O5 110.0(3) . . ? O6 P2 O5 111.5(3) . . ? O4 P2 C2 110.4(3) . . ? O6 P2 C2 103.3(3) . . ? O5 P2 C2 104.4(3) . . ? P1 O1 Eu1 148.0(3) . 2_755 ? P1 O2 Eu1 155.4(3) . . ? C4 O3 P1 113.5(4) . . ? P2 O4 Eu1 156.8(3) . 2_745 ? P2 O5 H5A 109.5 . . ? C5 O7 Eu1 117.2(4) . 3_755 ? C5 O8 Eu1 116.0(4) . . ? C6 O9 Eu1 120.2(4) . 3_765 ? C6 O10 Eu1 119.6(4) . . ? Eu1 O11 H11A 109.3 . . ? Eu1 O11 H11B 109.7 . . ? H11A O11 H11B 109.4 . . ? H1WA O1W H1WB 109.4 . . ? H2WC O2W H2WB 103.7 . . ? C2 N1 C1 109.6(5) . . ? C2 N1 C3 111.4(5) . . ? C1 N1 C3 110.0(5) . . ? C2 N1 H1A 108.5 . . ? C1 N1 H1A 107.9 . . ? C3 N1 H1A 109.4 . . ? N1 C1 P1 113.9(4) . . ? N1 C1 H1B 108.5 . . ? P1 C1 H1B 108.3 . . ? N1 C1 H1C 108.8 . . ? P1 C1 H1C 109.3 . . ? H1B C1 H1C 107.9 . . ? N1 C2 P2 119.4(4) . . ? N1 C2 H2A 108.0 . . ? P2 C2 H2A 108.0 . . ? N1 C2 H2B 106.8 . . ? P2 C2 H2B 107.0 . . ? H2A C2 H2B 107.2 . . ? C4 C3 N1 112.5(5) . . ? C4 C3 H3A 108.2 . . ? N1 C3 H3A 108.3 . . ? C4 C3 H3B 109.5 . . ? N1 C3 H3B 110.6 . . ? H3A C3 H3B 107.6 . . ? O3 C4 C3 111.2(5) . . ? O3 C4 H4B 108.5 . . ? C3 C4 H4B 109.3 . . ? O3 C4 H4A 110.2 . . ? C3 C4 H4A 109.7 . . ? H4B C4 H4A 107.9 . . ? O7 C5 O8 127.8(6) . . ? O7 C5 C5 114.6(7) . 3_755 ? O8 C5 C5 117.6(7) . 3_755 ? O7 C5 Eu1 161.0(4) . . ? O8 C5 Eu1 43.7(3) . . ? C5 C5 Eu1 77.0(5) 3_755 . ? O7 C5 Eu1 42.5(3) . 3_755 ? O8 C5 Eu1 160.0(4) . 3_755 ? C5 C5 Eu1 75.1(4) 3_755 3_755 ? Eu1 C5 Eu1 152.0(2) . 3_755 ? O10 C6 O9 126.4(5) . . ? O10 C6 C6 116.9(7) . 3_765 ? O9 C6 C6 116.7(6) . 3_765 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.969 _refine_diff_density_min -1.069 _refine_diff_density_rms 0.163 _database_code_depnum_ccdc_archive 'CCDC 706876'