# 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_gdno3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Gd N O8' _chemical_formula_sum 'C11 H14 Gd N O8' _chemical_formula_weight 445.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 P21/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 11.9099(2) _cell_length_b 13.3448(1) _cell_length_c 8.4333(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.2950(10) _cell_angle_gamma 90.00 _cell_volume 1332.27(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9126 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 28.78 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 5.018 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3144 _exptl_absorpt_correction_T_max 0.7875 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11284 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2729 _reflns_number_gt 2593 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0109P)^2^+1.2798P] 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 2729 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0170 _refine_ls_R_factor_gt 0.0159 _refine_ls_wR_factor_ref 0.0387 _refine_ls_wR_factor_gt 0.0383 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.004 _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 0.335649(9) 0.591494(7) 0.011971(12) 0.01001(5) Uani 1 1 d . . . O1 O 0.05610(16) 0.60885(13) -0.3826(2) 0.0245(4) Uani 1 1 d . . . O2 O 0.21202(14) 0.63046(12) -0.21393(19) 0.0161(3) Uani 1 1 d . . . O3 O 0.36743(13) 0.46744(11) 0.22500(18) 0.0142(3) Uani 1 1 d . . . O4 O 0.26888(15) 0.59971(11) 0.2794(2) 0.0150(3) Uani 1 1 d . . . O5 O 0.40356(14) 0.45451(12) -0.11763(18) 0.0164(3) Uani 1 1 d . . . O6 O 0.48602(13) 0.66376(11) 0.1950(2) 0.0159(3) Uani 1 1 d . . . O7 O 0.45899(14) 0.65857(12) -0.16482(19) 0.0182(3) Uani 1 1 d . . . H7A H 0.5115 0.6240 -0.1878 0.022 Uiso 1 1 d R . . H7B H 0.4690 0.7136 -0.2049 0.022 Uiso 1 1 d R . . O8 O 0.27962(15) 0.76112(12) 0.03651(19) 0.0188(4) Uani 1 1 d . . . H8A H 0.2607 0.7952 -0.0426 0.023 Uiso 1 1 d R . . H8B H 0.2577 0.7910 0.1119 0.023 Uiso 1 1 d R . . N1 N 0.16137(15) 0.47411(15) -0.0368(2) 0.0143(4) Uani 1 1 d . . . C1 C 0.1420(2) 0.38933(18) 0.0422(3) 0.0188(5) Uani 1 1 d . . . H1 H 0.1871 0.3762 0.1400 0.023 Uiso 1 1 calc R . . C2 C 0.0596(2) 0.31994(18) -0.0116(3) 0.0217(5) Uani 1 1 d . . . H2 H 0.0495 0.2605 0.0472 0.026 Uiso 1 1 calc R . . C3 C -0.0074(2) 0.33912(18) -0.1524(3) 0.0216(5) Uani 1 1 d . . . H3 H -0.0648 0.2932 -0.1918 0.026 Uiso 1 1 calc R . . C4 C 0.0101(2) 0.42637(18) -0.2355(3) 0.0196(5) Uani 1 1 d . . . H4 H -0.0350 0.4414 -0.3326 0.024 Uiso 1 1 calc R . . C5 C 0.09479(19) 0.49103(17) -0.1741(3) 0.0141(5) Uani 1 1 d . . . C6 C 0.1201(2) 0.58413(16) -0.2656(3) 0.0158(5) Uani 1 1 d . . . C7 C 0.31681(19) 0.51807(16) 0.3227(3) 0.0131(4) Uani 1 1 d . . . C8 C 0.3123(2) 0.48126(18) 0.4906(3) 0.0217(5) Uani 1 1 d . . . H8C H 0.2373 0.4978 0.5236 0.026 Uiso 1 1 calc R . . H8D H 0.3696 0.5180 0.5621 0.026 Uiso 1 1 calc R . . C9 C 0.33266(19) 0.36901(18) 0.5140(2) 0.0161(5) Uani 1 1 d . . . H9A H 0.4088 0.3521 0.4852 0.019 Uiso 1 1 calc R . . H9B H 0.2766 0.3316 0.4414 0.019 Uiso 1 1 calc R . . C10 C 0.32360(19) 0.33595(17) 0.6866(3) 0.0143(5) Uani 1 1 d . . . H10A H 0.2504 0.3586 0.7192 0.017 Uiso 1 1 calc R . . H10B H 0.3256 0.2619 0.6925 0.017 Uiso 1 1 calc R . . C11 C 0.58130(19) 0.62149(16) 0.1998(3) 0.0125(4) 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 0.01422(7) 0.00792(7) 0.00785(7) -0.00025(4) 0.00111(4) -0.00021(4) O1 0.0283(10) 0.0217(9) 0.0209(9) 0.0042(7) -0.0091(8) 0.0002(7) O2 0.0205(9) 0.0139(8) 0.0133(8) 0.0017(6) -0.0008(7) -0.0030(6) O3 0.0193(8) 0.0135(8) 0.0104(7) 0.0009(6) 0.0041(6) 0.0029(6) O4 0.0197(9) 0.0139(8) 0.0119(8) 0.0013(6) 0.0034(7) 0.0027(6) O5 0.0248(9) 0.0105(8) 0.0144(8) -0.0023(6) 0.0046(7) 0.0004(6) O6 0.0159(8) 0.0134(8) 0.0177(8) -0.0035(6) -0.0014(6) 0.0012(6) O7 0.0202(9) 0.0130(8) 0.0227(9) 0.0078(7) 0.0090(7) 0.0045(6) O8 0.0333(10) 0.0114(8) 0.0119(8) -0.0004(6) 0.0025(7) 0.0072(7) N1 0.0152(10) 0.0137(10) 0.0143(9) 0.0006(7) 0.0027(8) 0.0009(7) C1 0.0224(13) 0.0156(11) 0.0182(12) 0.0013(9) 0.0011(10) -0.0007(9) C2 0.0228(13) 0.0157(11) 0.0274(13) 0.0024(10) 0.0062(10) -0.0036(9) C3 0.0159(12) 0.0192(12) 0.0299(14) -0.0030(10) 0.0030(10) -0.0038(9) C4 0.0177(12) 0.0195(11) 0.0208(13) -0.0022(10) -0.0014(10) 0.0018(9) C5 0.0139(11) 0.0136(11) 0.0153(11) -0.0033(9) 0.0036(9) 0.0026(8) C6 0.0212(12) 0.0130(11) 0.0133(12) -0.0029(8) 0.0018(9) 0.0021(8) C7 0.0150(11) 0.0139(11) 0.0102(11) -0.0011(8) 0.0000(8) -0.0013(8) C8 0.0373(14) 0.0164(12) 0.0122(12) 0.0028(9) 0.0060(10) 0.0078(10) C9 0.0216(13) 0.0141(12) 0.0118(12) -0.0007(8) -0.0014(9) 0.0011(9) C10 0.0151(11) 0.0139(11) 0.0134(11) 0.0005(9) -0.0003(9) -0.0012(8) C11 0.0175(11) 0.0105(10) 0.0096(10) 0.0027(8) 0.0026(9) -0.0013(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 2.3203(15) . ? Gd1 O2 2.3351(15) . ? Gd1 O8 2.3754(15) . ? Gd1 O7 2.3795(16) . ? Gd1 O6 2.4317(16) . ? Gd1 O3 2.4418(15) . ? Gd1 O4 2.4750(17) . ? Gd1 N1 2.5970(19) . ? Gd1 C7 2.830(2) . ? O1 C6 1.224(3) . ? O2 C6 1.291(3) . ? O3 C7 1.268(3) . ? O4 C7 1.265(3) . ? O5 C11 1.253(3) 3_665 ? O6 C11 1.264(3) . ? O7 H7A 0.8168 . ? O7 H7B 0.8227 . ? O8 H8A 0.8185 . ? O8 H8B 0.8174 . ? N1 C1 1.346(3) . ? N1 C5 1.349(3) . ? C1 C2 1.389(3) . ? C1 H1 0.9500 . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.510(3) . ? C7 C8 1.505(3) . ? C8 C9 1.527(3) . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 C10 1.536(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.512(3) 3_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O5 1.253(3) 3_665 ? C11 C10 1.512(3) 3_666 ? 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 O5 Gd1 O2 90.71(6) . . ? O5 Gd1 O8 155.17(6) . . ? O2 Gd1 O8 72.59(6) . . ? O5 Gd1 O7 74.35(6) . . ? O2 Gd1 O7 77.43(6) . . ? O8 Gd1 O7 83.96(6) . . ? O5 Gd1 O6 109.93(5) . . ? O2 Gd1 O6 141.64(5) . . ? O8 Gd1 O6 76.18(5) . . ? O7 Gd1 O6 77.65(6) . . ? O5 Gd1 O3 77.20(5) . . ? O2 Gd1 O3 141.65(5) . . ? O8 Gd1 O3 127.18(5) . . ? O7 Gd1 O3 131.26(5) . . ? O6 Gd1 O3 75.99(5) . . ? O5 Gd1 O4 128.87(5) . . ? O2 Gd1 O4 119.79(6) . . ? O8 Gd1 O4 75.94(5) . . ? O7 Gd1 O4 146.77(6) . . ? O6 Gd1 O4 72.05(6) . . ? O3 Gd1 O4 53.05(5) . . ? O5 Gd1 N1 76.35(6) . . ? O2 Gd1 N1 65.38(6) . . ? O8 Gd1 N1 111.18(6) . . ? O7 Gd1 N1 131.70(6) . . ? O6 Gd1 N1 149.32(6) . . ? O3 Gd1 N1 76.37(6) . . ? O4 Gd1 N1 80.80(6) . . ? O5 Gd1 C7 103.33(6) . . ? O2 Gd1 C7 136.53(6) . . ? O8 Gd1 C7 101.41(6) . . ? O7 Gd1 C7 145.85(6) . . ? O6 Gd1 C7 71.17(6) . . ? O3 Gd1 C7 26.55(6) . . ? O4 Gd1 C7 26.53(6) . . ? N1 Gd1 C7 78.16(6) . . ? C6 O2 Gd1 127.17(14) . . ? C7 O3 Gd1 94.05(13) . . ? C7 O4 Gd1 92.58(13) . . ? C11 O5 Gd1 167.77(15) 3_665 . ? C11 O6 Gd1 116.08(14) . . ? Gd1 O7 H7A 118.5 . . ? Gd1 O7 H7B 136.1 . . ? H7A O7 H7B 104.9 . . ? Gd1 O8 H8A 120.9 . . ? Gd1 O8 H8B 130.5 . . ? H8A O8 H8B 106.3 . . ? C1 N1 C5 116.7(2) . . ? C1 N1 Gd1 127.30(15) . . ? C5 N1 Gd1 114.81(14) . . ? N1 C1 C2 123.5(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 123.5(2) . . ? N1 C5 C6 116.4(2) . . ? C4 C5 C6 120.0(2) . . ? O1 C6 O2 124.9(2) . . ? O1 C6 C5 119.5(2) . . ? O2 C6 C5 115.5(2) . . ? O4 C7 O3 120.2(2) . . ? O4 C7 C8 119.4(2) . . ? O3 C7 C8 120.39(19) . . ? O4 C7 Gd1 60.90(12) . . ? O3 C7 Gd1 59.40(11) . . ? C8 C7 Gd1 177.21(17) . . ? C7 C8 C9 114.87(19) . . ? C7 C8 H8C 108.6 . . ? C9 C8 H8C 108.6 . . ? C7 C8 H8D 108.6 . . ? C9 C8 H8D 108.6 . . ? H8C C8 H8D 107.5 . . ? C8 C9 C10 112.21(19) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.53(18) 3_666 . ? C11 C10 H10A 109.3 3_666 . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 3_666 . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? O5 C11 O6 121.8(2) 3_665 . ? O5 C11 C10 120.8(2) 3_665 3_666 ? O6 C11 C10 117.41(19) . 3_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.655 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 949215' ####################################################################### # # 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_tbno3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N O8 Tb' _chemical_formula_sum 'C11 H14 N O8 Tb' _chemical_formula_weight 447.15 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' 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 P21/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 11.9132(7) _cell_length_b 13.2782(8) _cell_length_c 8.4139(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.390(2) _cell_angle_gamma 90.00 _cell_volume 1322.69(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9918 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 28.39 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 5.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4121 _exptl_absorpt_correction_T_max 0.7381 _exptl_absorpt_process_details 'SADABS; Sheldrick, 2004' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18464 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3288 _reflns_number_gt 3029 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART, (Bruker, 2004)' _computing_cell_refinement 'Bruker SAINT, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2004)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0123P)^2^+0.6708P] 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 3288 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0181 _refine_ls_R_factor_gt 0.0156 _refine_ls_wR_factor_ref 0.0370 _refine_ls_wR_factor_gt 0.0362 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 Tb1 Tb 0.335287(8) 0.591508(7) 0.011818(10) 0.00906(4) Uani 1 1 d . . . O1 O 0.05804(14) 0.60849(11) -0.38368(19) 0.0221(4) Uani 1 1 d . . . O2 O 0.21353(12) 0.63008(11) -0.21393(16) 0.0144(3) Uani 1 1 d . . . O3 O 0.36810(12) 0.46753(10) 0.22407(15) 0.0131(3) Uani 1 1 d . . . O4 O 0.26928(13) 0.60011(10) 0.27807(17) 0.0134(3) Uani 1 1 d . . . O5 O 0.40223(12) 0.45533(10) -0.11778(16) 0.0145(3) Uani 1 1 d . . . O6 O 0.48517(12) 0.66235(10) 0.19316(17) 0.0145(3) Uani 1 1 d . . . O7 O 0.45752(12) 0.65896(10) -0.16429(17) 0.0165(3) Uani 1 1 d . . . H7A H 0.5100 0.6244 -0.1872 0.020 Uiso 1 1 d R . . H7B H 0.4675 0.7140 -0.2044 0.020 Uiso 1 1 d R . . O8 O 0.28049(13) 0.76084(10) 0.03639(16) 0.0176(3) Uani 1 1 d . . . H8A H 0.2616 0.7949 -0.0428 0.021 Uiso 1 1 d R . . H8B H 0.2585 0.7908 0.1118 0.021 Uiso 1 1 d R . . N1 N 0.16233(14) 0.47371(13) -0.03619(19) 0.0123(3) Uani 1 1 d . . . C1 C 0.14217(19) 0.38918(16) 0.0438(3) 0.0175(4) Uani 1 1 d . . . H1 H 0.1870 0.3762 0.1422 0.021 Uiso 1 1 calc R . . C2 C 0.05929(19) 0.31996(16) -0.0098(3) 0.0201(5) Uani 1 1 d . . . H2 H 0.0490 0.2604 0.0495 0.024 Uiso 1 1 calc R . . C3 C -0.00794(18) 0.33920(16) -0.1507(3) 0.0195(5) Uani 1 1 d . . . H3 H -0.0658 0.2934 -0.1898 0.023 Uiso 1 1 calc R . . C4 C 0.01044(19) 0.42652(16) -0.2341(3) 0.0175(4) Uani 1 1 d . . . H4 H -0.0348 0.4419 -0.3313 0.021 Uiso 1 1 calc R . . C5 C 0.09576(17) 0.49070(15) -0.1735(2) 0.0130(4) Uani 1 1 d . . . C6 C 0.12144(19) 0.58380(14) -0.2657(2) 0.0133(4) Uani 1 1 d . . . C7 C 0.31711(17) 0.51787(15) 0.3215(2) 0.0119(4) Uani 1 1 d . . . C8 C 0.3126(2) 0.48118(16) 0.4896(2) 0.0195(5) Uani 1 1 d . . . H8C H 0.2372 0.4972 0.5220 0.023 Uiso 1 1 calc R . . H8D H 0.3692 0.5187 0.5616 0.023 Uiso 1 1 calc R . . C9 C 0.33417(18) 0.36892(17) 0.5136(2) 0.0152(4) Uani 1 1 d . . . H9A H 0.4106 0.3527 0.4855 0.018 Uiso 1 1 calc R . . H9B H 0.2788 0.3307 0.4404 0.018 Uiso 1 1 calc R . . C10 C 0.32496(17) 0.33556(15) 0.6863(2) 0.0127(4) Uani 1 1 d . . . H10A H 0.2513 0.3575 0.7182 0.015 Uiso 1 1 calc R . . H10B H 0.3280 0.2611 0.6923 0.015 Uiso 1 1 calc R . . C11 C 0.58130(17) 0.62088(15) 0.1997(2) 0.0109(4) 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 Tb1 0.01291(6) 0.00731(6) 0.00692(5) -0.00027(3) 0.00089(4) -0.00017(3) O1 0.0251(9) 0.0199(8) 0.0190(8) 0.0031(6) -0.0077(7) 0.0005(7) O2 0.0172(8) 0.0126(7) 0.0127(7) 0.0015(6) -0.0011(6) -0.0023(6) O3 0.0168(7) 0.0125(7) 0.0103(6) 0.0002(5) 0.0034(6) 0.0023(6) O4 0.0168(8) 0.0121(7) 0.0114(7) 0.0009(5) 0.0016(6) 0.0029(6) O5 0.0220(8) 0.0095(7) 0.0123(7) -0.0015(5) 0.0027(6) 0.0003(6) O6 0.0120(7) 0.0136(7) 0.0173(7) -0.0031(6) -0.0007(6) 0.0011(6) O7 0.0184(8) 0.0111(7) 0.0213(7) 0.0068(6) 0.0084(6) 0.0028(6) O8 0.0317(9) 0.0111(7) 0.0098(6) 0.0003(5) 0.0022(6) 0.0073(6) N1 0.0143(9) 0.0105(9) 0.0122(8) 0.0007(6) 0.0028(7) -0.0005(6) C1 0.0214(12) 0.0155(10) 0.0154(10) 0.0032(8) 0.0008(9) -0.0004(9) C2 0.0211(12) 0.0148(11) 0.0250(11) 0.0027(9) 0.0054(9) -0.0022(9) C3 0.0145(11) 0.0166(11) 0.0276(11) -0.0036(9) 0.0032(9) -0.0034(9) C4 0.0155(11) 0.0175(11) 0.0191(10) -0.0020(8) -0.0002(9) 0.0016(8) C5 0.0127(10) 0.0138(10) 0.0128(9) -0.0023(7) 0.0024(8) 0.0024(8) C6 0.0166(11) 0.0117(10) 0.0116(9) -0.0032(7) 0.0012(8) 0.0033(8) C7 0.0131(10) 0.0136(10) 0.0086(9) -0.0006(7) -0.0011(8) -0.0018(8) C8 0.0347(13) 0.0154(11) 0.0090(9) 0.0023(8) 0.0048(9) 0.0076(9) C9 0.0223(12) 0.0147(11) 0.0081(9) -0.0013(7) 0.0002(8) 0.0005(8) C10 0.0149(10) 0.0126(10) 0.0105(9) 0.0008(7) 0.0004(8) -0.0007(8) C11 0.0158(10) 0.0095(9) 0.0079(8) 0.0016(7) 0.0032(7) -0.0016(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 2.2996(14) . ? Tb1 O2 2.3154(13) . ? Tb1 O8 2.3568(14) . ? Tb1 O7 2.3661(14) . ? Tb1 O6 2.4072(14) . ? Tb1 O3 2.4283(13) . ? Tb1 O4 2.4581(15) . ? Tb1 N1 2.5826(16) . ? Tb1 C7 2.8138(19) . ? O1 C6 1.223(3) . ? O2 C6 1.290(2) . ? O3 C7 1.264(2) . ? O4 C7 1.267(2) . ? O5 C11 1.252(2) 3_665 ? O6 C11 1.266(2) . ? O7 H7A 0.8157 . ? O7 H7B 0.8192 . ? O8 H8A 0.8157 . ? O8 H8B 0.8156 . ? N1 C1 1.344(3) . ? N1 C5 1.346(3) . ? C1 C2 1.387(3) . ? C1 H1 0.9500 . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 C6 1.509(3) . ? C7 C8 1.503(3) . ? C8 C9 1.522(3) . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 C10 1.535(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.504(3) 3_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O5 1.252(2) 3_665 ? C11 C10 1.504(3) 3_666 ? 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 O5 Tb1 O2 90.21(5) . . ? O5 Tb1 O8 154.93(5) . . ? O2 Tb1 O8 72.93(5) . . ? O5 Tb1 O7 74.37(5) . . ? O2 Tb1 O7 77.03(5) . . ? O8 Tb1 O7 83.66(5) . . ? O5 Tb1 O6 109.63(5) . . ? O2 Tb1 O6 141.84(5) . . ? O8 Tb1 O6 76.39(5) . . ? O7 Tb1 O6 77.54(5) . . ? O5 Tb1 O3 77.28(5) . . ? O2 Tb1 O3 142.01(5) . . ? O8 Tb1 O3 127.28(5) . . ? O7 Tb1 O3 131.09(5) . . ? O6 Tb1 O3 75.61(5) . . ? O5 Tb1 O4 129.18(5) . . ? O2 Tb1 O4 120.17(5) . . ? O8 Tb1 O4 75.87(5) . . ? O7 Tb1 O4 146.59(5) . . ? O6 Tb1 O4 72.19(5) . . ? O3 Tb1 O4 53.34(4) . . ? O5 Tb1 N1 76.25(5) . . ? O2 Tb1 N1 65.77(5) . . ? O8 Tb1 N1 111.57(5) . . ? O7 Tb1 N1 131.85(5) . . ? O6 Tb1 N1 149.14(5) . . ? O3 Tb1 N1 76.39(5) . . ? O4 Tb1 N1 80.80(5) . . ? O5 Tb1 C7 103.43(5) . . ? O2 Tb1 C7 136.95(5) . . ? O8 Tb1 C7 101.52(5) . . ? O7 Tb1 C7 145.85(5) . . ? O6 Tb1 C7 71.15(5) . . ? O3 Tb1 C7 26.63(5) . . ? O4 Tb1 C7 26.73(5) . . ? N1 Tb1 C7 78.00(5) . . ? C6 O2 Tb1 127.09(12) . . ? C7 O3 Tb1 93.94(11) . . ? C7 O4 Tb1 92.49(12) . . ? C11 O5 Tb1 168.63(14) 3_665 . ? C11 O6 Tb1 117.46(12) . . ? Tb1 O7 H7A 118.5 . . ? Tb1 O7 H7B 136.3 . . ? H7A O7 H7B 104.7 . . ? Tb1 O8 H8A 120.8 . . ? Tb1 O8 H8B 130.4 . . ? H8A O8 H8B 106.3 . . ? C1 N1 C5 116.66(18) . . ? C1 N1 Tb1 127.69(13) . . ? C5 N1 Tb1 114.61(13) . . ? N1 C1 C2 123.5(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.7(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 118.8(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 123.59(19) . . ? N1 C5 C6 116.41(18) . . ? C4 C5 C6 119.96(18) . . ? O1 C6 O2 124.84(19) . . ? O1 C6 C5 119.64(19) . . ? O2 C6 C5 115.48(17) . . ? O4 C7 O3 120.13(17) . . ? O4 C7 C8 119.25(18) . . ? O3 C7 C8 120.61(17) . . ? O4 C7 Tb1 60.78(10) . . ? O3 C7 Tb1 59.43(10) . . ? C8 C7 Tb1 177.24(15) . . ? C7 C8 C9 114.75(16) . . ? C7 C8 H8C 108.6 . . ? C9 C8 H8C 108.6 . . ? C7 C8 H8D 108.6 . . ? C9 C8 H8D 108.6 . . ? H8C C8 H8D 107.6 . . ? C8 C9 C10 112.28(16) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.50(17) 3_666 . ? C11 C10 H10A 109.3 3_666 . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 3_666 . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? O5 C11 O6 121.58(18) 3_665 . ? O5 C11 C10 120.74(18) 3_665 3_666 ? O6 C11 C10 117.65(17) . 3_666 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.642 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 872792' ####################################################################### # # 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_dyp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Dy N O8' _chemical_formula_sum 'C11 H14 Dy N O8' _chemical_formula_weight 450.73 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.9640(3) _cell_length_b 13.2553(5) _cell_length_c 8.4017(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.4550(10) _cell_angle_gamma 90.00 _cell_volume 1323.95(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5508 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.07 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 5.684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1317 _exptl_absorpt_correction_T_max 0.8045 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9720 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2693 _reflns_number_gt 2409 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0134P)^2^+0.6348P] 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 2693 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0216 _refine_ls_R_factor_gt 0.0174 _refine_ls_wR_factor_ref 0.0398 _refine_ls_wR_factor_gt 0.0385 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Dy1 Dy 0.334996(10) 0.591628(10) 0.011240(14) 0.00788(5) Uani 1 1 d . . . O1 O 0.05932(18) 0.60873(16) -0.3847(3) 0.0196(5) Uani 1 1 d . . . O2 O 0.21440(16) 0.63034(15) -0.2135(2) 0.0133(4) Uani 1 1 d . . . O3 O 0.36847(16) 0.46792(15) 0.2230(2) 0.0122(4) Uani 1 1 d . . . O4 O 0.26915(16) 0.60028(14) 0.2764(2) 0.0126(4) Uani 1 1 d . . . O5 O 0.40181(16) 0.45562(15) -0.1176(2) 0.0127(4) Uani 1 1 d . . . O6 O 0.48436(15) 0.66177(15) 0.1914(2) 0.0122(4) Uani 1 1 d . . . O7 O 0.45701(16) 0.65912(15) -0.1634(2) 0.0159(5) Uani 1 1 d . . . H7A H 0.5095 0.6246 -0.1863 0.019 Uiso 1 1 d R . . H7B H 0.4670 0.7142 -0.2034 0.019 Uiso 1 1 d R . . O8 O 0.28099(16) 0.76068(15) 0.0359(2) 0.0158(4) Uani 1 1 d . . . H8A H 0.2621 0.7948 -0.0432 0.019 Uiso 1 1 d R . . H8B H 0.2590 0.7906 0.1113 0.019 Uiso 1 1 d R . . N1 N 0.16318(18) 0.47418(19) -0.0354(3) 0.0116(5) Uani 1 1 d . . . C1 C 0.1434(2) 0.3895(2) 0.0456(4) 0.0155(6) Uani 1 1 d . . . H1 H 0.1883 0.3766 0.1442 0.019 Uiso 1 1 calc R . . C2 C 0.0605(3) 0.3202(2) -0.0082(4) 0.0182(7) Uani 1 1 d . . . H2 H 0.0511 0.2602 0.0508 0.022 Uiso 1 1 calc R . . C3 C -0.0077(2) 0.3394(2) -0.1478(4) 0.0173(7) Uani 1 1 d . . . H3 H -0.0662 0.2939 -0.1855 0.021 Uiso 1 1 calc R . . C4 C 0.0107(2) 0.4267(2) -0.2328(4) 0.0169(7) Uani 1 1 d . . . H4 H -0.0349 0.4421 -0.3298 0.020 Uiso 1 1 calc R . . C5 C 0.0965(2) 0.4908(2) -0.1735(3) 0.0120(6) Uani 1 1 d . . . C6 C 0.1224(2) 0.5840(2) -0.2659(3) 0.0124(6) Uani 1 1 d . . . C7 C 0.3171(2) 0.5184(2) 0.3205(3) 0.0108(6) Uani 1 1 d . . . C8 C 0.3131(3) 0.4812(2) 0.4887(3) 0.0178(7) Uani 1 1 d . . . H8C H 0.2380 0.4967 0.5212 0.021 Uiso 1 1 calc R . . H8D H 0.3693 0.5190 0.5608 0.021 Uiso 1 1 calc R . . C9 C 0.3354(2) 0.3686(2) 0.5127(3) 0.0145(6) Uani 1 1 d . . . H9A H 0.4118 0.3528 0.4849 0.017 Uiso 1 1 calc R . . H9B H 0.2807 0.3300 0.4392 0.017 Uiso 1 1 calc R . . C10 C 0.3262(2) 0.3348(2) 0.6867(3) 0.0122(6) Uani 1 1 d . . . H10A H 0.2526 0.3562 0.7183 0.015 Uiso 1 1 calc R . . H10B H 0.3300 0.2603 0.6929 0.015 Uiso 1 1 calc R . . C11 C 0.5808(2) 0.6206(2) 0.1991(3) 0.0101(6) 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 Dy1 0.01117(7) 0.00680(8) 0.00557(8) -0.00028(5) 0.00041(5) 0.00001(5) O1 0.0229(12) 0.0180(12) 0.0156(12) 0.0027(9) -0.0075(9) -0.0013(9) O2 0.0167(10) 0.0122(11) 0.0108(10) 0.0015(8) 0.0003(8) -0.0032(8) O3 0.0172(10) 0.0116(11) 0.0081(10) 0.0004(8) 0.0030(8) 0.0019(8) O4 0.0148(10) 0.0126(11) 0.0102(10) 0.0012(8) 0.0011(8) 0.0013(8) O5 0.0202(11) 0.0082(10) 0.0104(10) -0.0020(8) 0.0042(8) 0.0008(8) O6 0.0124(10) 0.0114(11) 0.0122(10) -0.0015(8) -0.0008(8) 0.0021(8) O7 0.0180(11) 0.0108(11) 0.0205(12) 0.0075(9) 0.0087(9) 0.0024(8) O8 0.0274(11) 0.0135(11) 0.0065(10) 0.0005(8) 0.0019(8) 0.0070(9) N1 0.0135(12) 0.0123(13) 0.0091(12) 0.0012(10) 0.0017(10) 0.0020(9) C1 0.0201(15) 0.0138(16) 0.0125(15) 0.0027(12) 0.0007(12) 0.0000(12) C2 0.0208(16) 0.0114(16) 0.0231(17) 0.0045(13) 0.0046(13) -0.0013(12) C3 0.0125(14) 0.0155(16) 0.0241(17) -0.0022(13) 0.0032(13) -0.0039(12) C4 0.0171(15) 0.0166(17) 0.0168(16) -0.0027(13) 0.0015(13) 0.0010(12) C5 0.0116(14) 0.0120(15) 0.0133(15) -0.0023(12) 0.0047(12) 0.0047(11) C6 0.0147(14) 0.0128(16) 0.0098(15) -0.0034(12) 0.0018(11) 0.0039(11) C7 0.0116(13) 0.0123(15) 0.0081(15) 0.0000(11) -0.0001(11) -0.0019(11) C8 0.0315(18) 0.0134(17) 0.0092(16) 0.0019(12) 0.0045(13) 0.0054(13) C9 0.0214(16) 0.0123(16) 0.0089(15) 0.0008(12) -0.0015(12) 0.0012(12) C10 0.0162(14) 0.0116(15) 0.0088(15) 0.0010(11) 0.0008(11) -0.0013(11) C11 0.0155(14) 0.0085(14) 0.0070(14) 0.0039(11) 0.0047(11) -0.0012(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Dy1 O5 2.2923(19) . ? Dy1 O2 2.301(2) . ? Dy1 O8 2.348(2) . ? Dy1 O7 2.3591(18) . ? Dy1 O6 2.3960(19) . ? Dy1 O3 2.4199(19) . ? Dy1 O4 2.4477(19) . ? Dy1 N1 2.573(2) . ? Dy1 C7 2.804(3) . ? O1 C6 1.227(4) . ? O2 C6 1.294(3) . ? O3 C7 1.268(3) . ? O4 C7 1.263(3) . ? O5 C11 1.251(3) 3_665 ? O6 C11 1.271(3) . ? O7 H7A 0.8175 . ? O7 H7B 0.8180 . ? O8 H8A 0.8145 . ? O8 H8B 0.8152 . ? N1 C1 1.347(4) . ? N1 C5 1.350(4) . ? C1 C2 1.390(4) . ? C1 H1 0.9500 . ? C2 C3 1.376(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.510(4) . ? C7 C8 1.503(4) . ? C8 C9 1.526(4) . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 C10 1.545(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.507(4) 3_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O5 1.251(3) 3_665 ? C11 C10 1.507(4) 3_666 ? 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 O5 Dy1 O2 90.45(7) . . ? O5 Dy1 O8 155.01(7) . . ? O2 Dy1 O8 72.92(7) . . ? O5 Dy1 O7 74.43(7) . . ? O2 Dy1 O7 77.29(7) . . ? O8 Dy1 O7 83.61(7) . . ? O5 Dy1 O6 109.18(7) . . ? O2 Dy1 O6 141.81(7) . . ? O8 Dy1 O6 76.52(7) . . ? O7 Dy1 O6 77.06(7) . . ? O5 Dy1 O3 77.09(6) . . ? O2 Dy1 O3 142.28(7) . . ? O8 Dy1 O3 127.32(6) . . ? O7 Dy1 O3 130.65(7) . . ? O6 Dy1 O3 75.43(7) . . ? O5 Dy1 O4 129.16(7) . . ? O2 Dy1 O4 119.99(7) . . ? O8 Dy1 O4 75.81(6) . . ? O7 Dy1 O4 146.43(7) . . ? O6 Dy1 O4 72.56(6) . . ? O3 Dy1 O4 53.56(6) . . ? O5 Dy1 N1 76.55(7) . . ? O2 Dy1 N1 66.02(7) . . ? O8 Dy1 N1 111.58(7) . . ? O7 Dy1 N1 132.41(7) . . ? O6 Dy1 N1 149.01(7) . . ? O3 Dy1 N1 76.43(7) . . ? O4 Dy1 N1 80.42(7) . . ? O5 Dy1 C7 103.43(7) . . ? O2 Dy1 C7 136.98(7) . . ? O8 Dy1 C7 101.42(7) . . ? O7 Dy1 C7 145.53(7) . . ? O6 Dy1 C7 71.22(7) . . ? O3 Dy1 C7 26.83(7) . . ? O4 Dy1 C7 26.75(7) . . ? N1 Dy1 C7 77.81(7) . . ? C6 O2 Dy1 127.18(18) . . ? C7 O3 Dy1 93.71(17) . . ? C7 O4 Dy1 92.55(15) . . ? C11 O5 Dy1 169.09(19) 3_665 . ? C11 O6 Dy1 118.24(18) . . ? Dy1 O7 H7A 118.6 . . ? Dy1 O7 H7B 136.4 . . ? H7A O7 H7B 104.5 . . ? Dy1 O8 H8A 120.7 . . ? Dy1 O8 H8B 130.5 . . ? H8A O8 H8B 106.3 . . ? C1 N1 C5 116.8(3) . . ? C1 N1 Dy1 127.56(19) . . ? C5 N1 Dy1 114.61(18) . . ? N1 C1 C2 123.1(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 123.6(3) . . ? N1 C5 C6 116.1(3) . . ? C4 C5 C6 120.3(3) . . ? O1 C6 O2 124.9(3) . . ? O1 C6 C5 119.6(3) . . ? O2 C6 C5 115.4(2) . . ? O4 C7 O3 120.1(2) . . ? O4 C7 C8 119.8(2) . . ? O3 C7 C8 120.2(3) . . ? O4 C7 Dy1 60.71(14) . . ? O3 C7 Dy1 59.46(14) . . ? C8 C7 Dy1 177.2(2) . . ? C7 C8 C9 115.0(2) . . ? C7 C8 H8C 108.5 . . ? C9 C8 H8C 108.5 . . ? C7 C8 H8D 108.5 . . ? C9 C8 H8D 108.5 . . ? H8C C8 H8D 107.5 . . ? C8 C9 C10 112.2(2) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.3(2) 3_666 . ? C11 C10 H10A 109.4 3_666 . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 3_666 . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O5 C11 O6 121.7(3) 3_665 . ? O5 C11 C10 120.6(2) 3_665 3_666 ? O6 C11 C10 117.7(2) . 3_666 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.502 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 953182' ####################################################################### # # 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_erp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Er N O8' _chemical_formula_sum 'C11 H14 Er N O8' _chemical_formula_weight 455.49 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' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.0228(3) _cell_length_b 13.1583(3) _cell_length_c 8.3837(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.5140(10) _cell_angle_gamma 90.00 _cell_volume 1317.74(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4840 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 28.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 6.409 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2494 _exptl_absorpt_correction_T_max 0.6997 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8105 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2696 _reflns_number_gt 2375 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART, (Bruker, 2005)' _computing_cell_refinement 'Bruker SMART, (Bruker, 2005)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2005)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0131P)^2^+0.4087P] 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 2696 _refine_ls_number_parameters 190 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0200 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0451 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 Er1 Er 0.335321(11) 0.591503(11) 0.010551(16) 0.00817(6) Uani 1 1 d . . . O1 O 0.0633(2) 0.6091(2) -0.3864(3) 0.0212(6) Uani 1 1 d . . . O2 O 0.21703(19) 0.63106(19) -0.2143(3) 0.0127(5) Uani 1 1 d . . . O3 O 0.36952(18) 0.46767(19) 0.2202(3) 0.0122(5) Uani 1 1 d . . . O4 O 0.26928(19) 0.60038(18) 0.2725(3) 0.0113(5) Uani 1 1 d . . . O5 O 0.40113(18) 0.45674(19) -0.1172(3) 0.0121(5) Uani 1 1 d . . . O6 O 0.48357(18) 0.66066(18) 0.1895(3) 0.0124(5) Uani 1 1 d . . . O7 O 0.45533(19) 0.65928(19) -0.1625(3) 0.0157(5) Uani 1 1 d . . . H7A H 0.5078 0.6247 -0.1854 0.019 Uiso 1 1 d R . . H7B H 0.4654 0.7143 -0.2025 0.019 Uiso 1 1 d R . . O8 O 0.28320(19) 0.75947(18) 0.0351(3) 0.0147(5) Uani 1 1 d . . . H8A H 0.2643 0.7935 -0.0440 0.018 Uiso 1 1 d R . . H8B H 0.2613 0.7894 0.1105 0.018 Uiso 1 1 d R . . N1 N 0.1654(2) 0.4746(2) -0.0357(3) 0.0110(6) Uani 1 1 d . . . C1 C 0.1452(3) 0.3900(3) 0.0466(4) 0.0168(8) Uani 1 1 d . . . H1 H 0.1907 0.3766 0.1445 0.020 Uiso 1 1 calc R . . C2 C 0.0610(3) 0.3215(3) -0.0049(4) 0.0190(8) Uani 1 1 d . . . H2 H 0.0502 0.2622 0.0562 0.023 Uiso 1 1 calc R . . C3 C -0.0069(3) 0.3402(3) -0.1456(4) 0.0194(8) Uani 1 1 d . . . H3 H -0.0650 0.2942 -0.1830 0.023 Uiso 1 1 calc R . . C4 C 0.0117(3) 0.4282(3) -0.2319(4) 0.0157(8) Uani 1 1 d . . . H4 H -0.0339 0.4443 -0.3287 0.019 Uiso 1 1 calc R . . C5 C 0.0989(3) 0.4915(3) -0.1718(4) 0.0115(7) Uani 1 1 d . . . C6 C 0.1248(3) 0.5848(3) -0.2669(4) 0.0119(7) Uani 1 1 d . . . C7 C 0.3183(3) 0.5187(3) 0.3177(4) 0.0112(7) Uani 1 1 d . . . C8 C 0.3142(3) 0.4811(3) 0.4872(4) 0.0182(8) Uani 1 1 d . . . H8C H 0.2391 0.4961 0.5192 0.022 Uiso 1 1 calc R . . H8D H 0.3696 0.5198 0.5597 0.022 Uiso 1 1 calc R . . C9 C 0.3377(3) 0.3677(3) 0.5121(4) 0.0143(8) Uani 1 1 d . . . H9A H 0.4139 0.3524 0.4846 0.017 Uiso 1 1 calc R . . H9B H 0.2837 0.3282 0.4386 0.017 Uiso 1 1 calc R . . C10 C 0.3288(3) 0.3345(3) 0.6862(4) 0.0112(7) Uani 1 1 d . . . H10A H 0.2551 0.3556 0.7171 0.013 Uiso 1 1 calc R . . H10B H 0.3331 0.2594 0.6930 0.013 Uiso 1 1 calc R . . C11 C 0.5798(3) 0.6201(3) 0.1984(4) 0.0089(7) 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 Er1 0.01113(9) 0.00637(9) 0.00700(9) -0.00003(6) 0.00103(6) 0.00009(6) O1 0.0250(14) 0.0188(16) 0.0178(14) 0.0020(11) -0.0067(12) -0.0009(12) O2 0.0165(12) 0.0107(13) 0.0104(11) 0.0025(10) -0.0009(10) -0.0011(10) O3 0.0135(12) 0.0131(14) 0.0107(11) 0.0016(10) 0.0040(9) 0.0022(10) O4 0.0128(12) 0.0125(14) 0.0089(11) 0.0015(10) 0.0021(9) 0.0028(10) O5 0.0184(13) 0.0090(13) 0.0094(11) -0.0020(10) 0.0033(10) -0.0001(10) O6 0.0104(12) 0.0116(14) 0.0150(12) -0.0034(10) 0.0006(9) -0.0001(10) O7 0.0171(12) 0.0089(13) 0.0227(13) 0.0063(11) 0.0092(11) 0.0024(10) O8 0.0255(13) 0.0109(14) 0.0080(11) 0.0007(10) 0.0027(10) 0.0068(11) N1 0.0112(14) 0.0117(17) 0.0104(14) -0.0001(12) 0.0024(12) 0.0010(12) C1 0.0182(18) 0.016(2) 0.0171(18) 0.0008(16) 0.0047(15) -0.0001(15) C2 0.0191(19) 0.018(2) 0.0209(19) 0.0011(16) 0.0061(16) -0.0071(16) C3 0.0124(18) 0.020(2) 0.026(2) -0.0067(17) 0.0010(15) -0.0046(16) C4 0.0121(17) 0.016(2) 0.0187(18) -0.0019(15) -0.0006(14) 0.0025(15) C5 0.0101(16) 0.0127(19) 0.0120(17) -0.0019(14) 0.0018(14) 0.0037(14) C6 0.0121(17) 0.013(2) 0.0106(17) -0.0053(14) 0.0004(14) 0.0027(14) C7 0.0117(16) 0.012(2) 0.0095(17) 0.0002(14) 0.0005(13) 0.0001(14) C8 0.031(2) 0.016(2) 0.0076(17) 0.0001(15) 0.0041(15) 0.0036(16) C9 0.0199(19) 0.013(2) 0.0091(17) -0.0025(14) -0.0006(14) -0.0015(15) C10 0.0135(17) 0.0093(18) 0.0102(17) -0.0005(14) -0.0006(13) -0.0011(14) C11 0.0159(18) 0.0078(17) 0.0064(15) 0.0038(13) 0.0028(13) -0.0014(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Er1 O5 2.261(2) . ? Er1 O2 2.289(2) . ? Er1 O8 2.313(2) . ? Er1 O7 2.336(2) . ? Er1 O6 2.377(2) . ? Er1 O3 2.398(2) . ? Er1 O4 2.421(2) . ? Er1 N1 2.552(3) . ? Er1 C7 2.777(3) . ? O1 C6 1.219(4) . ? O2 C6 1.297(4) . ? O3 C7 1.270(4) . ? O4 C7 1.263(4) . ? O5 C11 1.254(4) 3_665 ? O6 C11 1.269(4) . ? O7 H7A 0.8181 . ? O7 H7B 0.8131 . ? O8 H8A 0.8116 . ? O8 H8B 0.8134 . ? N1 C5 1.335(4) . ? N1 C1 1.346(5) . ? C1 C2 1.388(5) . ? C1 H1 0.9500 . ? C2 C3 1.378(5) . ? C2 H2 0.9500 . ? C3 C4 1.398(5) . ? C3 H3 0.9500 . ? C4 C5 1.388(5) . ? C4 H4 0.9500 . ? C5 C6 1.516(5) . ? C7 C8 1.511(4) . ? C8 C9 1.528(6) . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 C10 1.539(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.504(5) 3_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O5 1.254(4) 3_665 ? C11 C10 1.504(5) 3_666 ? 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 O5 Er1 O2 90.36(8) . . ? O5 Er1 O8 154.78(8) . . ? O2 Er1 O8 72.94(8) . . ? O5 Er1 O7 74.40(8) . . ? O2 Er1 O7 76.80(8) . . ? O8 Er1 O7 83.29(8) . . ? O5 Er1 O6 108.77(8) . . ? O2 Er1 O6 141.65(9) . . ? O8 Er1 O6 76.66(8) . . ? O7 Er1 O6 76.95(8) . . ? O5 Er1 O3 76.95(8) . . ? O2 Er1 O3 142.85(8) . . ? O8 Er1 O3 127.57(8) . . ? O7 Er1 O3 130.39(8) . . ? O6 Er1 O3 75.13(8) . . ? O5 Er1 O4 129.50(8) . . ? O2 Er1 O4 119.93(8) . . ? O8 Er1 O4 75.71(8) . . ? O7 Er1 O4 146.52(8) . . ? O6 Er1 O4 73.05(8) . . ? O3 Er1 O4 54.16(7) . . ? O5 Er1 N1 76.83(8) . . ? O2 Er1 N1 66.42(8) . . ? O8 Er1 N1 111.68(9) . . ? O7 Er1 N1 132.54(8) . . ? O6 Er1 N1 148.96(8) . . ? O3 Er1 N1 76.67(8) . . ? O4 Er1 N1 80.08(8) . . ? O5 Er1 C7 103.62(9) . . ? O2 Er1 C7 137.56(9) . . ? O8 Er1 C7 101.41(9) . . ? O7 Er1 C7 145.42(9) . . ? O6 Er1 C7 71.06(9) . . ? O3 Er1 C7 27.16(9) . . ? O4 Er1 C7 27.03(8) . . ? N1 Er1 C7 77.94(9) . . ? C6 O2 Er1 126.9(2) . . ? C7 O3 Er1 93.3(2) . . ? C7 O4 Er1 92.35(18) . . ? C11 O5 Er1 170.0(2) 3_665 . ? C11 O6 Er1 119.3(2) . . ? Er1 O7 H7A 118.7 . . ? Er1 O7 H7B 136.7 . . ? H7A O7 H7B 104.1 . . ? Er1 O8 H8A 120.6 . . ? Er1 O8 H8B 130.3 . . ? H8A O8 H8B 106.4 . . ? C5 N1 C1 116.8(3) . . ? C5 N1 Er1 114.9(2) . . ? C1 N1 Er1 127.5(2) . . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.4(4) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 117.9(3) . . ? C5 C4 H4 121.1 . . ? C3 C4 H4 121.1 . . ? N1 C5 C4 124.4(3) . . ? N1 C5 C6 116.5(3) . . ? C4 C5 C6 119.1(3) . . ? O1 C6 O2 124.9(3) . . ? O1 C6 C5 120.2(3) . . ? O2 C6 C5 114.8(3) . . ? O4 C7 O3 120.1(3) . . ? O4 C7 C8 119.8(3) . . ? O3 C7 C8 120.2(3) . . ? O4 C7 Er1 60.61(16) . . ? O3 C7 Er1 59.56(16) . . ? C8 C7 Er1 177.4(2) . . ? C7 C8 C9 115.0(3) . . ? C7 C8 H8C 108.5 . . ? C9 C8 H8C 108.5 . . ? C7 C8 H8D 108.5 . . ? C9 C8 H8D 108.5 . . ? H8C C8 H8D 107.5 . . ? C8 C9 C10 112.0(3) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.9(3) 3_666 . ? C11 C10 H10A 109.2 3_666 . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 3_666 . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O5 C11 O6 122.0(3) 3_665 . ? O5 C11 C10 120.3(3) 3_665 3_666 ? O6 C11 C10 117.7(3) . 3_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.581 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 953183'