# 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_compound-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C40 H36 Dy2 N10 O22' _chemical_formula_sum 'C40 H36 Dy2 N10 O22' _chemical_formula_weight 1333.79 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6892(6) _cell_length_b 18.2050(10) _cell_length_c 12.5195(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.661(3) _cell_angle_gamma 90.00 _cell_volume 2294.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4038 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 3.330 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7357 _exptl_absorpt_correction_T_max 0.7518 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 12919 _diffrn_reflns_av_R_equivalents 0.0907 _diffrn_reflns_av_unetI/netI 0.1107 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4038 _reflns_number_gt 2456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0089P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4038 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _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 Dy1 Dy 1.38361(3) -0.022056(18) -0.15449(3) 0.02698(10) Uani 1 1 d . . . N1 N 1.6216(5) -0.0770(3) -0.3572(5) 0.0362(15) Uani 1 1 d . . . H1 H 1.5769 -0.0437 -0.3373 0.080 Uiso 1 1 calc . . . N2 N 1.3200(5) 0.1693(3) 0.0042(4) 0.0310(15) Uani 1 1 d . . . H99 H 1.3816 0.1534 -0.0199 0.080 Uiso 1 1 calc . . . N3 N 1.4864(6) 0.1067(4) -0.2410(6) 0.0446(18) Uani 1 1 d . . . N4 N 1.1406(6) 0.0442(3) -0.2977(6) 0.0488(18) Uani 1 1 d . . . N5 N 1.2609(7) -0.1568(4) -0.1196(6) 0.0518(19) Uani 1 1 d . . . O1 O 1.4449(4) -0.1060(2) -0.2517(4) 0.0388(13) Uani 1 1 d . . . O2 O 1.3961(3) 0.0259(2) 0.0213(3) 0.0278(10) Uani 1 1 d . . . O3 O 1.5003(5) 0.0425(2) -0.2681(4) 0.0463(15) Uani 1 1 d . . . O4 O 1.4199(5) 0.1135(3) -0.1755(4) 0.0491(14) Uani 1 1 d . . . O5 O 1.5326(6) 0.1586(3) -0.2715(6) 0.088(2) Uani 1 1 d . . . O6 O 1.2202(4) 0.0096(3) -0.3355(4) 0.0461(14) Uani 1 1 d . . . O7 O 1.1681(5) 0.0461(3) -0.1928(4) 0.0448(14) Uani 1 1 d . . . O8 O 1.0399(5) 0.0738(3) -0.3619(5) 0.076(2) Uani 1 1 d . . . O9 O 1.3731(5) -0.1384(3) -0.0503(5) 0.0537(16) Uani 1 1 d . . . O10 O 1.2014(4) -0.1087(3) -0.1887(5) 0.0554(16) Uani 1 1 d . . . O11 O 1.2147(6) -0.2174(3) -0.1203(6) 0.095(3) Uani 1 1 d . . . C1 C 1.7081(7) -0.0551(4) -0.4079(6) 0.040(2) Uani 1 1 d . . . C2 C 1.7811(7) -0.1098(5) -0.4378(7) 0.057(2) Uani 1 1 d . . . H2 H 1.8425 -0.0969 -0.4724 0.080 Uiso 1 1 calc . . . C3 C 1.7643(7) -0.1812(5) -0.4175(7) 0.049(2) Uani 1 1 d . . . H3 H 1.8160 -0.2162 -0.4370 0.080 Uiso 1 1 calc . . . C4 C 1.6693(7) -0.2047(4) -0.3668(6) 0.0348(19) Uani 1 1 d . . . C5 C 1.6445(7) -0.2768(4) -0.3444(8) 0.052(2) Uani 1 1 d . . . H5 H 1.6917 -0.3149 -0.3628 0.080 Uiso 1 1 calc . . . C6 C 1.5518(8) -0.2919(4) -0.2958(7) 0.050(2) Uani 1 1 d . . . H6 H 1.5328 -0.3406 -0.2850 0.080 Uiso 1 1 calc . . . C7 C 1.4841(7) -0.2359(4) -0.2616(6) 0.039(2) Uani 1 1 d . . . H7 H 1.4238 -0.2480 -0.2254 0.080 Uiso 1 1 calc . . . C8 C 1.5051(7) -0.1634(4) -0.2805(6) 0.0332(19) Uani 1 1 d . . . C9 C 1.5996(7) -0.1493(4) -0.3351(6) 0.0345(18) Uani 1 1 d . . . C10 C 1.7192(7) 0.0240(5) -0.4263(7) 0.059(2) Uani 1 1 d . . . H10A H 1.6580 0.0503 -0.3992 0.080 Uiso 1 1 calc . . . H10B H 1.6987 0.0334 -0.5058 0.080 Uiso 1 1 calc . . . H10C H 1.8081 0.0401 -0.3858 0.080 Uiso 1 1 calc . . . C11 C 1.2940(8) 0.2410(4) -0.0027(7) 0.045(2) Uani 1 1 d . . . C12 C 1.1934(8) 0.2660(4) 0.0399(7) 0.054(3) Uani 1 1 d . . . H12 H 1.1751 0.3160 0.0396 0.080 Uiso 1 1 calc . . . C13 C 1.1255(8) 0.2185(5) 0.0800(7) 0.054(3) Uani 1 1 d . . . H13 H 1.0599 0.2364 0.1064 0.080 Uiso 1 1 calc . . . C14 C 1.1490(7) 0.1427(5) 0.0839(6) 0.041(2) Uani 1 1 d . . . C15 C 1.0804(7) 0.0903(5) 0.1241(6) 0.054(3) Uani 1 1 d . . . H15 H 1.0128 0.1048 0.1507 0.080 Uiso 1 1 calc . . . C16 C 1.1123(7) 0.0190(5) 0.1243(6) 0.053(2) Uani 1 1 d . . . H16 H 1.0635 -0.0159 0.1476 0.080 Uiso 1 1 calc . . . C17 C 1.2183(6) -0.0037(4) 0.0898(6) 0.040(2) Uani 1 1 d . . . H17 H 1.2389 -0.0534 0.0916 0.080 Uiso 1 1 calc . . . C18 C 1.2916(6) 0.0454(4) 0.0537(5) 0.0278(17) Uani 1 1 d . . . C19 C 1.2533(6) 0.1189(4) 0.0479(5) 0.0280(17) Uani 1 1 d . . . C20 C 1.3727(8) 0.2882(4) -0.0522(8) 0.066(3) Uani 1 1 d . . . H20A H 1.4344 0.2585 -0.0739 0.080 Uiso 1 1 calc . . . H20B H 1.4206 0.3239 0.0029 0.080 Uiso 1 1 calc . . . H20C H 1.3143 0.3129 -0.1177 0.080 Uiso 1 1 calc . . . 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 0.02474(16) 0.03253(17) 0.02739(17) -0.0002(2) 0.01366(13) 0.0034(2) N1 0.032(3) 0.046(4) 0.034(4) -0.011(3) 0.016(3) -0.003(3) N2 0.028(3) 0.037(4) 0.024(3) -0.007(3) 0.002(3) 0.008(3) N3 0.038(4) 0.043(5) 0.056(5) 0.005(4) 0.019(4) 0.003(4) N4 0.041(4) 0.066(5) 0.039(4) 0.007(4) 0.014(4) 0.011(4) N5 0.050(5) 0.058(5) 0.057(5) 0.013(4) 0.030(4) -0.006(4) O1 0.044(3) 0.032(3) 0.050(4) -0.002(3) 0.028(3) -0.004(2) O2 0.026(2) 0.031(2) 0.031(3) -0.005(2) 0.017(2) -0.002(2) O3 0.063(3) 0.032(3) 0.062(4) 0.008(3) 0.043(3) 0.008(3) O4 0.067(4) 0.038(3) 0.051(4) 0.004(3) 0.031(3) -0.006(3) O5 0.093(5) 0.050(4) 0.136(7) 0.032(4) 0.058(5) -0.012(4) O6 0.039(3) 0.066(4) 0.036(3) 0.004(3) 0.017(3) 0.010(3) O7 0.042(3) 0.062(4) 0.035(3) -0.001(3) 0.020(3) 0.008(2) O8 0.049(4) 0.118(5) 0.049(4) 0.022(4) 0.002(3) 0.039(4) O9 0.047(3) 0.062(4) 0.051(4) 0.002(3) 0.015(3) -0.011(3) O10 0.028(3) 0.066(4) 0.073(4) 0.018(3) 0.018(3) 0.000(3) O11 0.099(5) 0.064(4) 0.104(6) 0.023(4) 0.012(5) -0.047(4) C1 0.041(5) 0.053(5) 0.034(5) -0.004(4) 0.021(4) -0.001(4) C2 0.046(5) 0.081(7) 0.059(6) 0.003(6) 0.037(5) 0.000(5) C3 0.038(5) 0.068(6) 0.049(6) -0.004(5) 0.024(5) 0.020(5) C4 0.030(4) 0.044(5) 0.026(4) -0.006(4) 0.003(4) -0.001(4) C5 0.054(6) 0.041(5) 0.053(6) -0.013(5) 0.008(5) 0.020(4) C6 0.062(6) 0.037(5) 0.042(6) 0.000(4) 0.006(5) -0.002(4) C7 0.052(5) 0.030(4) 0.033(5) -0.008(4) 0.010(4) -0.009(4) C8 0.026(4) 0.040(5) 0.031(5) -0.010(4) 0.006(4) -0.004(4) C9 0.037(4) 0.040(4) 0.029(4) -0.005(4) 0.014(4) 0.004(4) C10 0.067(5) 0.066(6) 0.059(6) 0.006(6) 0.040(5) -0.009(6) C11 0.049(5) 0.027(4) 0.040(5) -0.007(4) -0.009(4) 0.007(4) C12 0.050(5) 0.041(5) 0.052(6) -0.020(5) -0.007(5) 0.019(4) C13 0.046(5) 0.072(6) 0.033(5) -0.025(5) -0.001(5) 0.026(5) C14 0.030(4) 0.063(6) 0.029(5) -0.017(4) 0.009(4) 0.014(4) C15 0.030(5) 0.105(8) 0.032(5) -0.006(5) 0.016(4) 0.019(5) C16 0.034(4) 0.088(6) 0.045(5) 0.002(5) 0.024(4) -0.009(5) C17 0.036(4) 0.060(6) 0.031(4) -0.009(4) 0.019(4) -0.009(4) C18 0.020(3) 0.043(5) 0.023(4) -0.001(3) 0.010(3) 0.003(3) C19 0.025(4) 0.037(4) 0.019(4) -0.010(4) 0.003(3) 0.002(3) C20 0.086(7) 0.034(5) 0.069(7) -0.001(5) 0.016(6) -0.001(5) _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 Dy1 O1 2.187(5) . ? Dy1 O2 2.329(4) . ? Dy1 O2 2.385(3) 3_855 ? Dy1 O6 2.420(4) . ? Dy1 O10 2.430(5) . ? Dy1 O3 2.481(5) . ? Dy1 O9 2.510(5) . ? Dy1 O7 2.516(5) . ? Dy1 O4 2.526(5) . ? Dy1 N4 2.878(6) . ? Dy1 N5 2.883(7) . ? Dy1 N3 2.945(7) . ? N1 C1 1.346(9) . ? N1 C9 1.383(8) . ? N1 H1 0.8600 . ? N2 C11 1.332(8) . ? N2 C19 1.383(8) . ? N2 H99 0.8600 . ? N3 O5 1.187(7) . ? N3 O3 1.240(7) . ? N3 O4 1.260(7) . ? N4 O8 1.231(6) . ? N4 O7 1.246(7) . ? N4 O6 1.270(7) . ? N5 O11 1.208(7) . ? N5 O10 1.245(7) . ? N5 O9 1.265(7) . ? O1 C8 1.339(8) . ? O2 C18 1.358(7) . ? O2 Dy1 2.385(3) 3_855 ? C1 C2 1.392(10) . ? C1 C10 1.470(10) . ? C2 C3 1.347(10) . ? C2 H2 0.9300 . ? C3 C4 1.433(10) . ? C3 H3 0.9300 . ? C4 C5 1.386(9) . ? C4 C9 1.388(9) . ? C5 C6 1.354(11) . ? C5 H5 0.9300 . ? C6 C7 1.398(10) . ? C6 H6 0.9300 . ? C7 C8 1.373(8) . ? C7 H7 0.9300 . ? C8 C9 1.419(10) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.426(11) . ? C11 C20 1.477(11) . ? C12 C13 1.330(11) . ? C12 H12 0.9300 . ? C13 C14 1.401(10) . ? C13 H13 0.9300 . ? C14 C15 1.395(10) . ? C14 C19 1.404(9) . ? C15 C16 1.343(10) . ? C15 H15 0.9300 . ? C16 C17 1.403(9) . ? C16 H16 0.9300 . ? C17 C18 1.362(8) . ? C17 H17 0.9300 . ? C18 C19 1.394(8) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Dy1 O2 148.73(16) . . ? O1 Dy1 O2 87.62(15) . 3_855 ? O2 Dy1 O2 67.71(15) . 3_855 ? O1 Dy1 O6 84.43(17) . . ? O2 Dy1 O6 126.12(15) . . ? O2 Dy1 O6 153.34(15) 3_855 . ? O1 Dy1 O10 79.69(17) . . ? O2 Dy1 O10 101.38(17) . . ? O2 Dy1 O10 130.44(16) 3_855 . ? O6 Dy1 O10 72.93(18) . . ? O1 Dy1 O3 73.09(17) . . ? O2 Dy1 O3 118.98(15) . . ? O2 Dy1 O3 81.14(15) 3_855 . ? O6 Dy1 O3 72.20(16) . . ? O10 Dy1 O3 137.26(19) . . ? O1 Dy1 O9 76.89(17) . . ? O2 Dy1 O9 79.85(16) . . ? O2 Dy1 O9 79.54(15) 3_855 . ? O6 Dy1 O9 122.90(17) . . ? O10 Dy1 O9 50.96(16) . . ? O3 Dy1 O9 144.74(16) . . ? O1 Dy1 O7 131.69(16) . . ? O2 Dy1 O7 75.73(14) . . ? O2 Dy1 O7 140.60(15) 3_855 . ? O6 Dy1 O7 51.51(16) . . ? O10 Dy1 O7 70.03(16) . . ? O3 Dy1 O7 105.18(16) . . ? O9 Dy1 O7 108.50(16) . . ? O1 Dy1 O4 122.66(18) . . ? O2 Dy1 O4 76.73(16) . . ? O2 Dy1 O4 87.21(15) 3_855 . ? O6 Dy1 O4 75.95(15) . . ? O10 Dy1 O4 139.29(17) . . ? O3 Dy1 O4 49.70(16) . . ? O9 Dy1 O4 156.10(17) . . ? O7 Dy1 O4 70.18(16) . . ? O1 Dy1 N4 108.84(18) . . ? O2 Dy1 N4 100.65(17) . . ? O2 Dy1 N4 156.87(16) 3_855 . ? O6 Dy1 N4 25.93(16) . . ? O10 Dy1 N4 70.15(18) . . ? O3 Dy1 N4 88.10(17) . . ? O9 Dy1 N4 119.26(17) . . ? O7 Dy1 N4 25.60(16) . . ? O4 Dy1 N4 70.33(16) . . ? O1 Dy1 N5 74.13(18) . . ? O2 Dy1 N5 93.43(18) . . ? O2 Dy1 N5 105.17(18) 3_855 . ? O6 Dy1 N5 97.06(19) . . ? O10 Dy1 N5 25.30(15) . . ? O3 Dy1 N5 146.29(18) . . ? O9 Dy1 N5 25.97(15) . . ? O7 Dy1 N5 90.84(17) . . ? O4 Dy1 N5 160.16(18) . . ? N4 Dy1 N5 95.16(19) . . ? O1 Dy1 N3 97.62(19) . . ? O2 Dy1 N3 98.02(17) . . ? O2 Dy1 N3 82.96(15) 3_855 . ? O6 Dy1 N3 72.98(16) . . ? O10 Dy1 N3 145.90(18) . . ? O3 Dy1 N3 24.56(15) . . ? O9 Dy1 N3 161.83(16) . . ? O7 Dy1 N3 88.19(17) . . ? O4 Dy1 N3 25.15(16) . . ? N4 Dy1 N3 78.91(17) . . ? N5 Dy1 N3 167.9(2) . . ? C1 N1 C9 124.6(7) . . ? C1 N1 H1 117.7 . . ? C9 N1 H1 117.7 . . ? C11 N2 C19 123.4(6) . . ? C11 N2 H99 118.3 . . ? C19 N2 H99 118.3 . . ? O5 N3 O3 124.2(8) . . ? O5 N3 O4 121.1(8) . . ? O3 N3 O4 114.7(7) . . ? O5 N3 Dy1 177.1(6) . . ? O3 N3 Dy1 56.3(4) . . ? O4 N3 Dy1 58.5(4) . . ? O8 N4 O7 121.4(7) . . ? O8 N4 O6 121.5(7) . . ? O7 N4 O6 117.1(6) . . ? O8 N4 Dy1 177.1(5) . . ? O7 N4 Dy1 60.8(4) . . ? O6 N4 Dy1 56.4(3) . . ? O11 N5 O10 121.7(7) . . ? O11 N5 O9 122.5(7) . . ? O10 N5 O9 115.8(7) . . ? O11 N5 Dy1 169.1(6) . . ? O10 N5 Dy1 56.5(4) . . ? O9 N5 Dy1 60.3(4) . . ? C8 O1 Dy1 163.1(5) . . ? C18 O2 Dy1 126.1(3) . . ? C18 O2 Dy1 121.1(3) . 3_855 ? Dy1 O2 Dy1 112.29(15) . 3_855 ? N3 O3 Dy1 99.2(5) . . ? N3 O4 Dy1 96.4(4) . . ? N4 O6 Dy1 97.6(4) . . ? N4 O7 Dy1 93.6(4) . . ? N5 O9 Dy1 93.7(4) . . ? N5 O10 Dy1 98.2(4) . . ? N1 C1 C2 116.8(7) . . ? N1 C1 C10 117.9(7) . . ? C2 C1 C10 125.3(8) . . ? C3 C2 C1 121.1(8) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 122.1(7) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C9 118.2(7) . . ? C5 C4 C3 125.8(8) . . ? C9 C4 C3 116.0(7) . . ? C6 C5 C4 120.1(7) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.5(7) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 121.0(8) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O1 C8 C7 125.6(7) . . ? O1 C8 C9 118.3(7) . . ? C7 C8 C9 116.1(7) . . ? N1 C9 C4 119.3(7) . . ? N1 C9 C8 117.7(7) . . ? C4 C9 C8 123.0(7) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 117.2(8) . . ? N2 C11 C20 117.5(8) . . ? C12 C11 C20 125.3(7) . . ? C13 C12 C11 120.6(7) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 122.7(8) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C15 C14 C13 125.2(8) . . ? C15 C14 C19 118.4(7) . . ? C13 C14 C19 116.4(8) . . ? C16 C15 C14 119.8(7) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.0(8) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 121.6(7) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? O2 C18 C17 123.4(6) . . ? O2 C18 C19 119.6(6) . . ? C17 C18 C19 117.0(6) . . ? N2 C19 C18 118.3(6) . . ? N2 C19 C14 119.6(6) . . ? C18 C19 C14 122.1(7) . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 H1 O3 0.86 2.09 2.937(7) 170.0 . N2 H99 O4 0.86 2.24 2.974(8) 142.9 . N2 H99 O9 0.86 2.48 3.183(7) 138.9 3_855 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.808 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 923350' ####################################################################### # # 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_compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C40 H36 Gd2 N10 O22' _chemical_formula_sum 'C40 H36 Gd2 N10 O22' _chemical_formula_weight 1323.29 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.716(2) _cell_length_b 18.234(4) _cell_length_c 12.561(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.75(3) _cell_angle_gamma 90.00 _cell_volume 2310.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5186 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 2.943 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9241 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Process-auto _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21977 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5186 _reflns_number_gt 4561 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0315P)^2^+0.8965P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5186 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0523 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _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 1.381656(13) -0.022765(7) -0.155965(10) 0.02461(6) Uani 1 1 d . . . N1 N 1.6219(2) -0.07754(15) -0.3579(2) 0.0338(6) Uani 1 1 d . . . H1 H 1.5770 -0.0443 -0.3383 0.080 Uiso 1 1 calc . . . N2 N 1.3190(3) 0.16912(13) 0.0042(2) 0.0338(6) Uani 1 1 d . . . H99 H 1.3801 0.1533 -0.0201 0.080 Uiso 1 1 calc . . . N3 N 1.4854(3) 0.10653(15) -0.2414(2) 0.0424(6) Uani 1 1 d . . . N4 N 1.1356(3) 0.04453(17) -0.3004(2) 0.0432(7) Uani 1 1 d . . . N5 N 1.2608(3) -0.15874(17) -0.1206(3) 0.0477(7) Uani 1 1 d . . . O1 O 1.4466(2) -0.10827(12) -0.25316(19) 0.0378(5) Uani 1 1 d . . . O2 O 1.3968(2) 0.02587(10) 0.02361(16) 0.0270(4) Uani 1 1 d . . . O3 O 1.4995(3) 0.04133(13) -0.2712(2) 0.0459(6) Uani 1 1 d . . . O4 O 1.4192(3) 0.11302(13) -0.17547(19) 0.0461(6) Uani 1 1 d . . . O5 O 1.5347(4) 0.15755(17) -0.2741(3) 0.0862(11) Uani 1 1 d . . . O6 O 1.2154(2) 0.01054(15) -0.33837(19) 0.0464(6) Uani 1 1 d . . . O7 O 1.1652(2) 0.04623(14) -0.19434(19) 0.0451(6) Uani 1 1 d . . . O8 O 1.0374(3) 0.0745(2) -0.3633(2) 0.0791(10) Uani 1 1 d . . . O9 O 1.3724(3) -0.14017(14) -0.0507(2) 0.0510(6) Uani 1 1 d . . . O10 O 1.1981(2) -0.11069(14) -0.1908(2) 0.0518(6) Uani 1 1 d . . . O11 O 1.2153(4) -0.21985(18) -0.1237(3) 0.0944(12) Uani 1 1 d . . . C1 C 1.7082(3) -0.0556(2) -0.4075(3) 0.0410(8) Uani 1 1 d . . . C2 C 1.7830(4) -0.1091(3) -0.4370(3) 0.0545(10) Uani 1 1 d . . . H2 H 1.8448 -0.0953 -0.4703 0.080 Uiso 1 1 calc . . . C3 C 1.7670(4) -0.1809(2) -0.4178(3) 0.0519(10) Uani 1 1 d . . . H3 H 1.8188 -0.2156 -0.4377 0.080 Uiso 1 1 calc . . . C4 C 1.6724(3) -0.20470(19) -0.3677(3) 0.0385(7) Uani 1 1 d . . . C5 C 1.6481(4) -0.2777(2) -0.3466(3) 0.0496(9) Uani 1 1 d . . . H5 H 1.6932 -0.3156 -0.3675 0.080 Uiso 1 1 calc . . . C6 C 1.5572(4) -0.29283(19) -0.2948(3) 0.0501(9) Uani 1 1 d . . . H6 H 1.5414 -0.3414 -0.2809 0.080 Uiso 1 1 calc . . . C7 C 1.4872(3) -0.23699(18) -0.2620(3) 0.0395(7) Uani 1 1 d . . . H7 H 1.4266 -0.2496 -0.2267 0.080 Uiso 1 1 calc . . . C8 C 1.5063(3) -0.16364(16) -0.2810(2) 0.0318(6) Uani 1 1 d . . . C9 C 1.6001(3) -0.14880(17) -0.3362(2) 0.0323(6) Uani 1 1 d . . . C10 C 1.7170(4) 0.0242(2) -0.4271(4) 0.0538(10) Uani 1 1 d . . . H10A H 1.6570 0.0502 -0.3986 0.080 Uiso 1 1 calc . . . H10B H 1.6938 0.0333 -0.5068 0.080 Uiso 1 1 calc . . . H10C H 1.8059 0.0408 -0.3887 0.080 Uiso 1 1 calc . . . C11 C 1.2940(4) 0.24079(18) -0.0028(3) 0.0462(9) Uani 1 1 d . . . C12 C 1.1944(4) 0.2659(2) 0.0386(3) 0.0602(12) Uani 1 1 d . . . H12 H 1.1762 0.3158 0.0372 0.080 Uiso 1 1 calc . . . C13 C 1.1252(4) 0.2189(2) 0.0803(3) 0.0554(11) Uani 1 1 d . . . H13 H 1.0598 0.2370 0.1065 0.080 Uiso 1 1 calc . . . C14 C 1.1502(3) 0.1430(2) 0.0848(2) 0.0411(8) Uani 1 1 d . . . C15 C 1.0813(3) 0.0904(3) 0.1250(3) 0.0515(10) Uani 1 1 d . . . H15 H 1.0135 0.1049 0.1510 0.080 Uiso 1 1 calc . . . C16 C 1.1136(4) 0.0186(2) 0.1258(3) 0.0509(10) Uani 1 1 d . . . H16 H 1.0647 -0.0161 0.1493 0.080 Uiso 1 1 calc . . . C17 C 1.2199(3) -0.0049(2) 0.0917(3) 0.0393(7) Uani 1 1 d . . . H17 H 1.2414 -0.0544 0.0950 0.080 Uiso 1 1 calc . . . C18 C 1.2920(3) 0.04468(16) 0.0539(2) 0.0270(6) Uani 1 1 d . . . C19 C 1.2541(3) 0.11893(17) 0.0474(2) 0.0304(6) Uani 1 1 d . . . C20 C 1.3716(5) 0.2885(2) -0.0524(4) 0.0695(13) Uani 1 1 d . . . H20A H 1.4338 0.2592 -0.0738 0.080 Uiso 1 1 calc . . . H20B H 1.4187 0.3244 0.0023 0.080 Uiso 1 1 calc . . . H20C H 1.3128 0.3128 -0.1180 0.080 Uiso 1 1 calc . . . 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 0.02385(8) 0.02725(8) 0.02612(8) -0.00034(5) 0.01290(6) 0.00293(5) N1 0.0314(14) 0.0406(14) 0.0335(13) -0.0078(10) 0.0161(10) -0.0017(11) N2 0.0345(14) 0.0314(13) 0.0326(13) -0.0046(10) 0.0075(10) 0.0070(11) N3 0.0385(16) 0.0367(15) 0.0525(17) 0.0119(12) 0.0161(13) -0.0004(12) N4 0.0310(15) 0.0568(17) 0.0414(16) 0.0067(13) 0.0117(12) 0.0091(13) N5 0.054(2) 0.0466(17) 0.0518(17) 0.0014(14) 0.0303(15) -0.0137(14) O1 0.0385(13) 0.0348(11) 0.0493(13) -0.0101(10) 0.0270(10) -0.0024(9) O2 0.0270(11) 0.0286(10) 0.0297(10) -0.0032(7) 0.0155(8) 0.0035(8) O3 0.0514(16) 0.0403(13) 0.0593(16) 0.0051(11) 0.0364(13) 0.0064(11) O4 0.0638(16) 0.0364(12) 0.0460(13) -0.0031(10) 0.0291(12) 0.0020(11) O5 0.098(3) 0.0528(18) 0.129(3) 0.0297(19) 0.067(2) -0.0096(17) O6 0.0403(14) 0.0681(17) 0.0340(12) 0.0054(11) 0.0166(10) 0.0149(12) O7 0.0412(14) 0.0602(15) 0.0370(12) 0.0027(11) 0.0171(10) 0.0167(11) O8 0.0479(18) 0.118(3) 0.0598(17) 0.0185(18) 0.0024(13) 0.0433(18) O9 0.0560(17) 0.0515(15) 0.0421(13) 0.0046(11) 0.0120(11) -0.0113(12) O10 0.0322(13) 0.0533(15) 0.0706(16) 0.0105(13) 0.0184(11) -0.0033(11) O11 0.109(3) 0.065(2) 0.095(2) 0.0202(18) 0.015(2) -0.047(2) C1 0.0339(18) 0.059(2) 0.0342(16) -0.0041(15) 0.0175(13) -0.0039(15) C2 0.047(2) 0.079(3) 0.049(2) -0.0084(19) 0.0313(17) 0.001(2) C3 0.040(2) 0.073(3) 0.049(2) -0.0162(18) 0.0233(16) 0.0104(18) C4 0.0326(17) 0.0476(19) 0.0349(16) -0.0126(14) 0.0110(13) 0.0074(14) C5 0.058(2) 0.0414(19) 0.046(2) -0.0090(15) 0.0142(17) 0.0188(17) C6 0.068(3) 0.0316(17) 0.047(2) -0.0034(14) 0.0137(18) 0.0076(16) C7 0.045(2) 0.0357(17) 0.0364(17) -0.0038(13) 0.0124(14) -0.0036(14) C8 0.0365(17) 0.0315(15) 0.0276(14) -0.0073(11) 0.0113(12) 0.0014(12) C9 0.0350(17) 0.0362(16) 0.0264(14) -0.0067(11) 0.0114(12) 0.0030(12) C10 0.050(2) 0.064(3) 0.055(2) 0.0011(18) 0.0288(19) -0.0115(18) C11 0.052(2) 0.0311(16) 0.0396(17) -0.0056(13) -0.0053(15) 0.0081(15) C12 0.067(3) 0.044(2) 0.051(2) -0.0173(17) -0.0049(19) 0.029(2) C13 0.043(2) 0.072(3) 0.043(2) -0.0210(18) 0.0044(16) 0.0294(19) C14 0.0334(17) 0.059(2) 0.0274(15) -0.0106(14) 0.0060(12) 0.0168(15) C15 0.0267(17) 0.096(3) 0.0361(17) -0.0070(18) 0.0161(13) 0.0139(18) C16 0.037(2) 0.082(3) 0.0397(18) 0.0007(18) 0.0210(15) -0.0083(18) C17 0.0360(18) 0.0490(18) 0.0366(17) 0.0018(14) 0.0172(14) -0.0035(14) C18 0.0240(14) 0.0357(14) 0.0233(13) -0.0031(11) 0.0106(10) 0.0041(11) C19 0.0284(15) 0.0378(16) 0.0240(13) -0.0069(11) 0.0076(11) 0.0059(12) C20 0.082(3) 0.034(2) 0.076(3) 0.0060(19) 0.005(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O1 2.232(2) . ? Gd1 O2 2.3778(19) . ? Gd1 O2 2.395(2) 3_855 ? Gd1 O6 2.457(2) . ? Gd1 O10 2.460(2) . ? Gd1 O3 2.508(2) . ? Gd1 O4 2.534(2) . ? Gd1 O9 2.536(2) . ? Gd1 O7 2.538(2) . ? Gd1 N5 2.900(3) . ? Gd1 N4 2.918(3) . ? Gd1 N3 2.958(3) . ? N1 C1 1.338(4) . ? N1 C9 1.364(4) . ? N1 H1 0.8600 . ? N2 C11 1.331(4) . ? N2 C19 1.368(4) . ? N2 H99 0.8600 . ? N3 O5 1.208(4) . ? N3 O4 1.264(4) . ? N3 O3 1.271(4) . ? N4 O8 1.212(4) . ? N4 O7 1.262(4) . ? N4 O6 1.271(4) . ? N5 O11 1.212(4) . ? N5 O10 1.264(4) . ? N5 O9 1.267(4) . ? O1 C8 1.304(4) . ? O2 C18 1.346(3) . ? O2 Gd1 2.395(2) 3_855 ? C1 C2 1.390(5) . ? C1 C10 1.484(5) . ? C2 C3 1.354(6) . ? C2 H2 0.9300 . ? C3 C4 1.430(5) . ? C3 H3 0.9300 . ? C4 C5 1.399(5) . ? C4 C9 1.415(4) . ? C5 C6 1.369(5) . ? C5 H5 0.9300 . ? C6 C7 1.407(5) . ? C6 H6 0.9300 . ? C7 C8 1.386(4) . ? C7 H7 0.9300 . ? C8 C9 1.427(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.412(6) . ? C11 C20 1.479(6) . ? C12 C13 1.349(6) . ? C12 H12 0.9300 . ? C13 C14 1.406(5) . ? C13 H13 0.9300 . ? C14 C15 1.405(6) . ? C14 C19 1.418(4) . ? C15 C16 1.354(6) . ? C15 H15 0.9300 . ? C16 C17 1.412(5) . ? C16 H16 0.9300 . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 C19 1.408(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Gd1 O2 147.75(8) . . ? O1 Gd1 O2 86.79(7) . 3_855 ? O2 Gd1 O2 67.45(8) . 3_855 ? O1 Gd1 O6 85.67(8) . . ? O2 Gd1 O6 126.02(7) . . ? O2 Gd1 O6 152.84(8) 3_855 . ? O1 Gd1 O10 79.97(8) . . ? O2 Gd1 O10 101.89(8) . . ? O2 Gd1 O10 130.83(7) 3_855 . ? O6 Gd1 O10 73.17(9) . . ? O1 Gd1 O3 72.48(8) . . ? O2 Gd1 O3 119.17(8) . . ? O2 Gd1 O3 80.63(8) 3_855 . ? O6 Gd1 O3 72.22(9) . . ? O10 Gd1 O3 136.83(9) . . ? O1 Gd1 O4 122.73(8) . . ? O2 Gd1 O4 76.42(7) . . ? O2 Gd1 O4 86.43(7) 3_855 . ? O6 Gd1 O4 75.94(9) . . ? O10 Gd1 O4 139.76(9) . . ? O3 Gd1 O4 50.31(7) . . ? O1 Gd1 O9 76.71(8) . . ? O2 Gd1 O9 79.75(7) . . ? O2 Gd1 O9 79.77(7) 3_855 . ? O6 Gd1 O9 123.45(8) . . ? O10 Gd1 O9 51.15(8) . . ? O3 Gd1 O9 144.15(8) . . ? O4 Gd1 O9 155.63(8) . . ? O1 Gd1 O7 132.57(8) . . ? O2 Gd1 O7 76.13(7) . . ? O2 Gd1 O7 140.50(7) 3_855 . ? O6 Gd1 O7 51.09(8) . . ? O10 Gd1 O7 70.39(9) . . ? O3 Gd1 O7 105.40(8) . . ? O4 Gd1 O7 70.25(8) . . ? O9 Gd1 O7 108.85(9) . . ? O1 Gd1 N5 74.01(8) . . ? O2 Gd1 N5 93.68(8) . . ? O2 Gd1 N5 105.22(8) 3_855 . ? O6 Gd1 N5 97.68(9) . . ? O10 Gd1 N5 25.63(8) . . ? O3 Gd1 N5 145.57(8) . . ? O4 Gd1 N5 160.74(9) . . ? O9 Gd1 N5 25.86(8) . . ? O7 Gd1 N5 91.49(9) . . ? O1 Gd1 N4 109.68(9) . . ? O2 Gd1 N4 101.00(8) . . ? O2 Gd1 N4 156.48(8) 3_855 . ? O6 Gd1 N4 25.56(8) . . ? O10 Gd1 N4 70.31(9) . . ? O3 Gd1 N4 88.31(9) . . ? O4 Gd1 N4 70.65(9) . . ? O9 Gd1 N4 119.53(8) . . ? O7 Gd1 N4 25.54(8) . . ? N5 Gd1 N4 95.65(9) . . ? O1 Gd1 N3 97.67(8) . . ? O2 Gd1 N3 97.66(7) . . ? O2 Gd1 N3 82.23(7) 3_855 . ? O6 Gd1 N3 73.01(8) . . ? O10 Gd1 N3 146.18(8) . . ? O3 Gd1 N3 25.20(8) . . ? O4 Gd1 N3 25.13(8) . . ? O9 Gd1 N3 161.39(8) . . ? O7 Gd1 N3 88.13(8) . . ? N5 Gd1 N3 168.21(8) . . ? N4 Gd1 N3 79.08(8) . . ? C1 N1 C9 124.8(3) . . ? C1 N1 H1 117.6 . . ? C9 N1 H1 117.6 . . ? C11 N2 C19 124.4(3) . . ? C11 N2 H99 117.8 . . ? C19 N2 H99 117.8 . . ? O5 N3 O4 123.8(3) . . ? O5 N3 O3 120.7(3) . . ? O4 N3 O3 115.4(3) . . ? O5 N3 Gd1 176.3(3) . . ? O4 N3 Gd1 58.30(15) . . ? O3 N3 Gd1 57.16(15) . . ? O8 N4 O7 122.0(3) . . ? O8 N4 O6 121.4(3) . . ? O7 N4 O6 116.6(3) . . ? O8 N4 Gd1 176.5(3) . . ? O7 N4 Gd1 60.13(15) . . ? O6 N4 Gd1 56.48(15) . . ? O11 N5 O10 120.1(3) . . ? O11 N5 O9 122.9(3) . . ? O10 N5 O9 117.0(3) . . ? O11 N5 Gd1 167.7(3) . . ? O10 N5 Gd1 57.33(15) . . ? O9 N5 Gd1 60.80(16) . . ? C8 O1 Gd1 163.6(2) . . ? C18 O2 Gd1 124.54(17) . . ? C18 O2 Gd1 122.41(16) . 3_855 ? Gd1 O2 Gd1 112.55(8) . 3_855 ? N3 O3 Gd1 97.64(18) . . ? N3 O4 Gd1 96.57(17) . . ? N4 O6 Gd1 97.96(18) . . ? N4 O7 Gd1 94.34(17) . . ? N5 O9 Gd1 93.34(18) . . ? N5 O10 Gd1 97.04(18) . . ? N1 C1 C2 117.7(3) . . ? N1 C1 C10 117.6(3) . . ? C2 C1 C10 124.6(3) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C9 118.6(3) . . ? C5 C4 C3 125.2(3) . . ? C9 C4 C3 116.2(3) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 122.0(3) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? O1 C8 C7 125.9(3) . . ? O1 C8 C9 118.2(3) . . ? C7 C8 C9 115.9(3) . . ? N1 C9 C4 118.9(3) . . ? N1 C9 C8 118.3(3) . . ? C4 C9 C8 122.8(3) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 117.0(4) . . ? N2 C11 C20 118.4(4) . . ? C12 C11 C20 124.6(4) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 121.2(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 124.8(3) . . ? C15 C14 C19 118.3(3) . . ? C13 C14 C19 116.9(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.4(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 120.8(3) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O2 C18 C17 123.4(3) . . ? O2 C18 C19 118.7(3) . . ? C17 C18 C19 117.9(3) . . ? N2 C19 C18 119.4(3) . . ? N2 C19 C14 119.1(3) . . ? C18 C19 C14 121.5(3) . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 H1 O3 0.86 2.08 2.928(3) 170.2 . N2 H99 O4 0.86 2.25 2.988(3) 143.4 . N2 H99 O9 0.86 2.51 3.202(4) 138.3 3_855 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.472 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 923351' ####################################################################### # # 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_compound-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C44 H48 Cl6 Dy2 N4 O6' _chemical_formula_sum 'C44 H48 Cl6 Dy2 N4 O6' _chemical_formula_weight 1266.56 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' Cl Cl 0.1484 0.1585 '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 10.910(2) _cell_length_b 12.189(2) _cell_length_c 18.974(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.93(3) _cell_angle_gamma 90.00 _cell_volume 2426.3(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5007 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 3.435 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9241 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Process-auto _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23355 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_unetI/netI 0.0702 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5507 _reflns_number_gt 4055 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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. Two restraints were made. H99 is a hydrogen atom in the ethanol molecule, determined from the difference Fourier maps. The position of H99 is unreasonable. Therefore we restricted the distance of H-O and C-H, to enable the H-O distance and H-O-C angle to fall in a normal range. ; _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^)+(0.0184P)^2^+2.3139P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5507 _refine_ls_number_parameters 283 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy -0.01867(2) -0.127673(17) 0.055269(13) 0.02837(8) Uani 1 1 d . . . Cl1 Cl 0.19489(14) -0.08952(12) 0.15862(8) 0.0561(4) Uani 1 1 d . . . Cl2 Cl -0.15440(13) -0.15656(11) 0.14761(8) 0.0497(4) Uani 1 1 d . . . Cl3 Cl -0.22351(12) -0.17584(11) -0.05504(8) 0.0452(3) Uani 1 1 d . . . N1 N -0.0585(4) -0.3914(3) -0.0896(2) 0.0390(10) Uani 1 1 d . . . H1 H -0.0961 -0.3414 -0.0713 0.080 Uiso 1 1 calc . . . N2 N 0.3212(4) -0.0997(3) 0.0137(2) 0.0373(10) Uani 1 1 d . . . H2 H 0.2819 -0.0562 0.0359 0.080 Uiso 1 1 calc . . . O1 O 0.0544(3) -0.2841(2) 0.0362(2) 0.0409(9) Uani 1 1 d . . . O2 O 0.0697(3) -0.0549(2) -0.03525(17) 0.0284(7) Uani 1 1 d . . . O3 O 0.4147(8) 0.0130(6) 0.2985(4) 0.156(3) Uani 1 1 d D . . C1 C -0.1228(6) -0.4363(4) -0.1528(3) 0.0527(15) Uani 1 1 d . . . C2 C -0.0595(8) -0.5183(5) -0.1813(4) 0.072(2) Uani 1 1 d . . . H2A H -0.1011 -0.5518 -0.2254 0.080 Uiso 1 1 calc . . . C3 C 0.0597(9) -0.5495(5) -0.1462(4) 0.075(2) Uani 1 1 d . . . H3A H 0.0985 -0.6043 -0.1666 0.080 Uiso 1 1 calc . . . C4 C 0.1278(6) -0.5011(4) -0.0790(3) 0.0530(16) Uani 1 1 d . . . C5 C 0.2528(7) -0.5270(5) -0.0384(4) 0.072(2) Uani 1 1 d . . . H5 H 0.2969 -0.5824 -0.0547 0.080 Uiso 1 1 calc . . . C6 C 0.3098(6) -0.4723(5) 0.0243(4) 0.0635(19) Uani 1 1 d . . . H6 H 0.3928 -0.4904 0.0500 0.080 Uiso 1 1 calc . . . C7 C 0.2458(6) -0.3884(4) 0.0515(3) 0.0521(15) Uani 1 1 d . . . H7 H 0.2871 -0.3516 0.0944 0.080 Uiso 1 1 calc . . . C8 C 0.1208(5) -0.3607(4) 0.0142(3) 0.0382(12) Uani 1 1 d . . . C9 C 0.0643(5) -0.4194(4) -0.0513(3) 0.0402(13) Uani 1 1 d . . . C10 C -0.2536(7) -0.3994(5) -0.1886(4) 0.0656(18) Uani 1 1 d . . . H10A H -0.2774 -0.3431 -0.1594 0.080 Uiso 1 1 calc . . . H10B H -0.3111 -0.4602 -0.1934 0.080 Uiso 1 1 calc . . . H10C H -0.2576 -0.3707 -0.2362 0.080 Uiso 1 1 calc . . . C11 C 0.4460(5) -0.1181(4) 0.0450(3) 0.0454(14) Uani 1 1 d . . . C12 C 0.5096(5) -0.1887(5) 0.0094(4) 0.0559(16) Uani 1 1 d . . . H12 H 0.5957 -0.2034 0.0298 0.080 Uiso 1 1 calc . . . C13 C 0.4462(6) -0.2365(5) -0.0553(4) 0.0599(18) Uani 1 1 d . . . H13 H 0.4903 -0.2837 -0.0781 0.080 Uiso 1 1 calc . . . C14 C 0.3153(5) -0.2164(4) -0.0887(3) 0.0407(13) Uani 1 1 d . . . C15 C 0.2433(6) -0.2618(4) -0.1554(3) 0.0480(15) Uani 1 1 d . . . H15 H 0.2815 -0.3087 -0.1818 0.080 Uiso 1 1 calc . . . C16 C 0.1178(6) -0.2367(4) -0.1809(3) 0.0450(14) Uani 1 1 d . . . H16 H 0.0710 -0.2664 -0.2253 0.080 Uiso 1 1 calc . . . C17 C 0.0560(5) -0.1665(4) -0.1420(3) 0.0378(12) Uani 1 1 d . . . H17 H -0.0304 -0.1518 -0.1609 0.080 Uiso 1 1 calc . . . C18 C 0.1211(4) -0.1201(3) -0.0772(3) 0.0291(10) Uani 1 1 d . . . C19 C 0.2528(4) -0.1455(3) -0.0508(3) 0.0304(11) Uani 1 1 d . . . C20 C 0.5072(5) -0.0615(5) 0.1153(4) 0.0612(17) Uani 1 1 d . . . H20A H 0.4452 -0.0169 0.1293 0.080 Uiso 1 1 calc . . . H20B H 0.5755 -0.0160 0.1094 0.080 Uiso 1 1 calc . . . H20C H 0.5404 -0.1151 0.1528 0.080 Uiso 1 1 calc . . . C21 C 0.4094(11) 0.1266(8) 0.2920(7) 0.129(4) Uani 1 1 d D . . H21A H 0.4314 0.1585 0.3408 0.080 Uiso 1 1 calc . . . H21B H 0.3224 0.1480 0.2676 0.080 Uiso 1 1 calc . . . C22 C 0.4930(10) 0.1718(8) 0.2520(5) 0.113(3) Uani 1 1 d . . . H22A H 0.4856 0.2502 0.2505 0.080 Uiso 1 1 calc . . . H22B H 0.4695 0.1433 0.2029 0.080 Uiso 1 1 calc . . . H22C H 0.5795 0.1516 0.2759 0.080 Uiso 1 1 calc . . . H99 H 0.371(7) -0.0311(15) 0.267(3) 0.135 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.02759(12) 0.03013(11) 0.02824(13) 0.00113(11) 0.00910(9) 0.00329(10) Cl1 0.0454(8) 0.0744(9) 0.0406(9) 0.0032(7) -0.0015(7) -0.0078(7) Cl2 0.0479(8) 0.0634(8) 0.0455(9) 0.0024(7) 0.0257(7) 0.0048(6) Cl3 0.0323(7) 0.0598(8) 0.0403(8) -0.0069(6) 0.0046(6) -0.0033(6) N1 0.057(3) 0.030(2) 0.033(3) 0.0027(19) 0.018(2) -0.0037(19) N2 0.032(2) 0.043(2) 0.038(3) 0.0020(19) 0.011(2) 0.0096(18) O1 0.043(2) 0.0339(17) 0.045(2) -0.0017(16) 0.0116(18) 0.0074(15) O2 0.0256(17) 0.0340(16) 0.0283(19) 0.0006(14) 0.0119(15) 0.0060(13) O3 0.160(7) 0.148(6) 0.130(7) 0.003(5) -0.011(5) -0.042(6) C1 0.080(5) 0.045(3) 0.036(4) -0.001(3) 0.021(3) -0.011(3) C2 0.116(6) 0.054(4) 0.048(4) -0.010(3) 0.025(5) -0.004(4) C3 0.141(7) 0.037(3) 0.065(5) -0.006(3) 0.060(5) 0.017(4) C4 0.085(5) 0.034(3) 0.051(4) 0.006(3) 0.037(4) 0.014(3) C5 0.093(6) 0.050(4) 0.089(6) 0.009(4) 0.054(5) 0.037(4) C6 0.058(4) 0.057(4) 0.077(5) 0.026(4) 0.022(4) 0.029(3) C7 0.058(4) 0.044(3) 0.056(4) 0.012(3) 0.020(3) 0.007(3) C8 0.047(3) 0.029(2) 0.043(3) 0.006(2) 0.020(3) 0.004(2) C9 0.055(3) 0.025(2) 0.047(4) 0.011(2) 0.025(3) 0.008(2) C10 0.077(5) 0.072(4) 0.040(4) -0.008(3) 0.002(3) -0.019(4) C11 0.028(3) 0.058(3) 0.052(4) 0.019(3) 0.013(3) 0.011(2) C12 0.032(3) 0.070(4) 0.069(5) 0.017(4) 0.020(3) 0.014(3) C13 0.056(4) 0.057(4) 0.084(5) 0.013(4) 0.048(4) 0.022(3) C14 0.046(3) 0.037(3) 0.046(4) 0.007(2) 0.024(3) 0.011(2) C15 0.064(4) 0.042(3) 0.049(4) 0.002(3) 0.034(3) 0.011(3) C16 0.074(4) 0.042(3) 0.023(3) -0.004(2) 0.019(3) -0.008(3) C17 0.052(3) 0.028(2) 0.035(3) 0.007(2) 0.014(3) -0.003(2) C18 0.034(2) 0.028(2) 0.026(3) 0.002(2) 0.010(2) -0.004(2) C19 0.032(3) 0.032(2) 0.029(3) 0.002(2) 0.012(2) 0.0044(19) C20 0.036(3) 0.089(4) 0.051(4) -0.001(4) -0.001(3) -0.001(3) C21 0.137(9) 0.094(7) 0.168(12) -0.015(7) 0.064(9) -0.017(6) C22 0.144(9) 0.102(7) 0.089(8) -0.005(5) 0.025(7) 0.020(6) _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 Dy1 O1 2.135(3) . ? Dy1 O2 2.300(3) 3 ? Dy1 O2 2.361(3) . ? Dy1 Cl2 2.6098(14) . ? Dy1 Cl1 2.6424(17) . ? Dy1 Cl3 2.6743(16) . ? Dy1 Dy1 3.8368(7) 3 ? N1 C1 1.329(7) . ? N1 C9 1.380(7) . ? N1 H1 0.8600 . ? N2 C11 1.347(6) . ? N2 C19 1.366(6) . ? N2 H2 0.8600 . ? O1 C8 1.318(5) . ? O2 C18 1.351(5) . ? O2 Dy1 2.300(3) 3 ? O3 C21 1.391(10) . ? O3 H99 0.850(10) . ? C1 C2 1.405(9) . ? C1 C10 1.472(9) . ? C2 C3 1.343(10) . ? C2 H2A 0.9300 . ? C3 C4 1.416(9) . ? C3 H3A 0.9300 . ? C4 C9 1.396(7) . ? C4 C5 1.406(9) . ? C5 C6 1.358(10) . ? C5 H5 0.9300 . ? C6 C7 1.412(8) . ? C6 H6 0.9300 . ? C7 C8 1.394(8) . ? C7 H7 0.9300 . ? C8 C9 1.420(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.391(8) . ? C11 C20 1.488(8) . ? C12 C13 1.363(9) . ? C12 H12 0.9300 . ? C13 C14 1.416(8) . ? C13 H13 0.9300 . ? C14 C15 1.407(8) . ? C14 C19 1.414(6) . ? C15 C16 1.356(8) . ? C15 H15 0.9300 . ? C16 C17 1.417(7) . ? C16 H16 0.9300 . ? C17 C18 1.362(7) . ? C17 H17 0.9300 . ? C18 C19 1.420(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.447(13) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Dy1 O2 156.99(12) . 3 ? O1 Dy1 O2 88.06(12) . . ? O2 Dy1 O2 69.20(11) 3 . ? O1 Dy1 Cl2 107.48(10) . . ? O2 Dy1 Cl2 94.89(8) 3 . ? O2 Dy1 Cl2 163.58(7) . . ? O1 Dy1 Cl1 89.36(10) . . ? O2 Dy1 Cl1 94.38(9) 3 . ? O2 Dy1 Cl1 91.20(8) . . ? Cl2 Dy1 Cl1 94.17(5) . . ? O1 Dy1 Cl3 86.67(10) . . ? O2 Dy1 Cl3 88.33(8) 3 . ? O2 Dy1 Cl3 86.19(8) . . ? Cl2 Dy1 Cl3 89.40(5) . . ? Cl1 Dy1 Cl3 175.32(4) . . ? O1 Dy1 Dy1 122.07(10) . 3 ? O2 Dy1 Dy1 35.12(7) 3 3 ? O2 Dy1 Dy1 34.08(7) . 3 ? Cl2 Dy1 Dy1 129.89(3) . 3 ? Cl1 Dy1 Dy1 93.36(4) . 3 ? Cl3 Dy1 Dy1 86.65(3) . 3 ? C1 N1 C9 124.7(5) . . ? C1 N1 H1 117.6 . . ? C9 N1 H1 117.6 . . ? C11 N2 C19 124.3(4) . . ? C11 N2 H2 117.8 . . ? C19 N2 H2 117.8 . . ? C8 O1 Dy1 161.7(3) . . ? C18 O2 Dy1 126.3(3) . 3 ? C18 O2 Dy1 121.8(2) . . ? Dy1 O2 Dy1 110.80(11) 3 . ? C21 O3 H99 124(2) . . ? N1 C1 C2 116.5(6) . . ? N1 C1 C10 119.7(5) . . ? C2 C1 C10 123.8(6) . . ? C3 C2 C1 121.5(7) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 121.7(6) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C9 C4 C5 117.5(6) . . ? C9 C4 C3 116.4(6) . . ? C5 C4 C3 126.1(6) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 121.5(6) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 120.2(6) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? O1 C8 C7 123.8(5) . . ? O1 C8 C9 119.3(5) . . ? C7 C8 C9 116.8(5) . . ? N1 C9 C4 119.2(5) . . ? N1 C9 C8 117.5(4) . . ? C4 C9 C8 123.2(5) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 117.9(5) . . ? N2 C11 C20 117.9(5) . . ? C12 C11 C20 124.2(5) . . ? C13 C12 C11 120.2(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 122.0(5) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C19 118.0(5) . . ? C15 C14 C13 125.5(5) . . ? C19 C14 C13 116.4(5) . . ? C16 C15 C14 119.5(5) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 121.9(5) . . ? C15 C16 H16 119.0 . . ? C17 C16 H16 119.0 . . ? C18 C17 C16 121.1(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? O2 C18 C17 125.3(4) . . ? O2 C18 C19 117.6(4) . . ? C17 C18 C19 117.0(4) . . ? N2 C19 C14 119.0(4) . . ? N2 C19 C18 118.5(4) . . ? C14 C19 C18 122.4(5) . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 C22 114.0(10) . . ? O3 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? O3 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 H1 Cl3 0.86 2.52 3.350(4) 163.5 . N2 H2 Cl1 0.86 2.78 3.399(4) 130.6 . N2 H2 Cl3 0.86 2.94 3.672(4) 143.7 3 O3 H99 Cl1 0.850(10) 2.50(2) 3.295(7) 157(4) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.686 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 923352' ####################################################################### # # 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_compound-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C44 H48 Cl6 Gd2 N4 O6' _chemical_formula_sum 'C44 H48 Cl6 Gd2 N4 O6' _chemical_formula_weight 1256.06 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' Cl Cl 0.1484 0.1585 '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 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 10.883(2) _cell_length_b 12.170(2) _cell_length_c 18.594(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.43(3) _cell_angle_gamma 90.00 _cell_volume 2374.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5414 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 3.157 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9241 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Process-auto _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22624 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_unetI/netI 0.0286 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5414 _reflns_number_gt 4915 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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. Two restraints were made. H99 is a hydrogen atom in the ethanol molecule, determined from the difference Fourier maps. The position of H99 is unreasonable. Therefore we restricted the distance of H-O and C-H, to enable the H-O distance and H-O-C angle to fall in a normal range. ; _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^)+(0.0170P)^2^+7.1067P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5414 _refine_ls_number_parameters 283 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd -0.018562(14) -0.128220(12) 0.058359(8) 0.01426(5) Uani 1 1 d . . . Cl1 Cl 0.19405(8) -0.08455(9) 0.16343(5) 0.0323(2) Uani 1 1 d . . . Cl2 Cl -0.15819(8) -0.16052(7) 0.15310(4) 0.02319(17) Uani 1 1 d . . . Cl3 Cl -0.22435(8) -0.17594(8) -0.05508(5) 0.02517(17) Uani 1 1 d . . . N1 N -0.0630(4) -0.3929(2) -0.08937(18) 0.0335(8) Uani 1 1 d . . . H1 H -0.0983 -0.3416 -0.0701 0.080 Uiso 1 1 calc . . . N2 N 0.3230(2) -0.0965(2) 0.01753(15) 0.0184(5) Uani 1 1 d . . . H2 H 0.2817 -0.0531 0.0392 0.080 Uiso 1 1 calc . . . O1 O 0.0567(2) -0.28533(19) 0.03665(14) 0.0250(5) Uani 1 1 d . . . O2 O 0.0715(2) -0.05611(17) -0.03508(12) 0.0153(4) Uani 1 1 d . . . O3 O 0.4291(5) 0.0198(5) 0.3070(3) 0.116(2) Uani 1 1 d D . . C1 C -0.1331(6) -0.4398(3) -0.1526(2) 0.0494(14) Uani 1 1 d . . . C2 C -0.0738(8) -0.5220(4) -0.1841(3) 0.072(2) Uani 1 1 d . . . H2A H -0.1183 -0.5551 -0.2285 0.080 Uiso 1 1 calc . . . C3 C 0.0464(9) -0.5540(4) -0.1514(3) 0.080(2) Uani 1 1 d . . . H3A H 0.0825 -0.6097 -0.1733 0.080 Uiso 1 1 calc . . . C4 C 0.1203(6) -0.5043(3) -0.0838(3) 0.0577(17) Uani 1 1 d . . . C5 C 0.2448(7) -0.5317(4) -0.0463(4) 0.073(2) Uani 1 1 d . . . H5 H 0.2865 -0.5877 -0.0644 0.080 Uiso 1 1 calc . . . C6 C 0.3061(6) -0.4765(4) 0.0172(4) 0.0644(19) Uani 1 1 d . . . H6 H 0.3896 -0.4956 0.0413 0.080 Uiso 1 1 calc . . . C7 C 0.2460(4) -0.3904(3) 0.0476(3) 0.0438(12) Uani 1 1 d . . . H7 H 0.2903 -0.3536 0.0905 0.080 Uiso 1 1 calc . . . C8 C 0.1211(4) -0.3623(3) 0.0125(2) 0.0321(9) Uani 1 1 d . . . C9 C 0.0592(5) -0.4202(3) -0.0535(2) 0.0370(11) Uani 1 1 d . . . C10 C -0.2655(6) -0.4024(4) -0.1858(2) 0.0520(14) Uani 1 1 d . . . H10A H -0.2827 -0.3391 -0.1592 0.080 Uiso 1 1 calc . . . H10B H -0.3237 -0.4603 -0.1824 0.080 Uiso 1 1 calc . . . H10C H -0.2761 -0.3836 -0.2372 0.080 Uiso 1 1 calc . . . C11 C 0.4463(3) -0.1129(3) 0.04984(19) 0.0227(7) Uani 1 1 d . . . C12 C 0.5136(3) -0.1842(3) 0.0140(2) 0.0286(8) Uani 1 1 d . . . H12 H 0.5998 -0.1974 0.0354 0.080 Uiso 1 1 calc . . . C13 C 0.4534(3) -0.2339(3) -0.0517(2) 0.0266(8) Uani 1 1 d . . . H13 H 0.4994 -0.2806 -0.0744 0.080 Uiso 1 1 calc . . . C14 C 0.3227(3) -0.2160(3) -0.08579(19) 0.0202(7) Uani 1 1 d . . . C15 C 0.2536(4) -0.2641(3) -0.1535(2) 0.0245(7) Uani 1 1 d . . . H15 H 0.2942 -0.3108 -0.1796 0.080 Uiso 1 1 calc . . . C16 C 0.1266(3) -0.2416(3) -0.18064(19) 0.0231(7) Uani 1 1 d . . . H16 H 0.0814 -0.2738 -0.2252 0.080 Uiso 1 1 calc . . . C17 C 0.0622(3) -0.1703(3) -0.14248(17) 0.0180(6) Uani 1 1 d . . . H17 H -0.0241 -0.1560 -0.1625 0.080 Uiso 1 1 calc . . . C18 C 0.1263(3) -0.1219(2) -0.07585(17) 0.0147(6) Uani 1 1 d . . . C19 C 0.2578(3) -0.1445(2) -0.04825(17) 0.0163(6) Uani 1 1 d . . . C20 C 0.5043(3) -0.0550(3) 0.1214(2) 0.0318(8) Uani 1 1 d . . . H20A H 0.4413 -0.0093 0.1341 0.080 Uiso 1 1 calc . . . H20B H 0.5740 -0.0103 0.1160 0.080 Uiso 1 1 calc . . . H20C H 0.5350 -0.1081 0.1602 0.080 Uiso 1 1 calc . . . C21 C 0.4020(11) 0.1381(6) 0.2870(7) 0.139(5) Uani 1 1 d D . . H21A H 0.3167 0.1460 0.2542 0.080 Uiso 1 1 calc . . . H21B H 0.4076 0.1812 0.3316 0.080 Uiso 1 1 calc . . . C22 C 0.4934(11) 0.1754(7) 0.2505(5) 0.113(3) Uani 1 1 d . . . H22A H 0.4914 0.2542 0.2479 0.080 Uiso 1 1 calc . . . H22B H 0.4738 0.1456 0.2009 0.080 Uiso 1 1 calc . . . H22C H 0.5768 0.1516 0.2779 0.080 Uiso 1 1 calc . . . H99 H 0.367(3) -0.0226(14) 0.287(3) 0.100 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.01437(8) 0.01564(8) 0.01339(8) 0.00131(6) 0.00479(5) 0.00180(6) Cl1 0.0233(4) 0.0512(6) 0.0189(4) 0.0054(4) -0.0001(3) -0.0060(4) Cl2 0.0230(4) 0.0293(4) 0.0205(4) 0.0006(3) 0.0114(3) 0.0020(3) Cl3 0.0192(4) 0.0352(5) 0.0208(4) -0.0056(3) 0.0048(3) -0.0046(3) N1 0.065(2) 0.0173(14) 0.0282(16) 0.0003(13) 0.0297(17) -0.0044(15) N2 0.0159(13) 0.0208(13) 0.0187(13) 0.0009(11) 0.0053(11) 0.0025(10) O1 0.0301(13) 0.0190(12) 0.0308(13) 0.0040(10) 0.0164(11) 0.0067(10) O2 0.0146(10) 0.0175(11) 0.0147(10) -0.0019(9) 0.0052(8) 0.0025(8) O3 0.099(4) 0.159(5) 0.115(4) -0.081(4) 0.071(3) -0.081(4) C1 0.112(4) 0.022(2) 0.026(2) -0.0008(17) 0.039(3) -0.017(2) C2 0.171(7) 0.020(2) 0.041(3) -0.001(2) 0.055(4) 0.007(3) C3 0.196(8) 0.019(2) 0.056(3) 0.009(2) 0.086(5) 0.028(3) C4 0.120(5) 0.021(2) 0.057(3) 0.019(2) 0.068(3) 0.030(3) C5 0.135(6) 0.036(3) 0.082(4) 0.029(3) 0.090(4) 0.048(3) C6 0.077(4) 0.045(3) 0.096(5) 0.044(3) 0.067(4) 0.043(3) C7 0.046(2) 0.032(2) 0.068(3) 0.029(2) 0.040(2) 0.0165(18) C8 0.047(2) 0.0176(17) 0.044(2) 0.0126(16) 0.034(2) 0.0089(16) C9 0.072(3) 0.0151(16) 0.041(2) 0.0091(16) 0.046(2) 0.0105(18) C10 0.093(4) 0.042(3) 0.024(2) -0.0081(19) 0.020(2) -0.025(3) C11 0.0172(15) 0.0268(17) 0.0244(17) 0.0071(14) 0.0060(13) 0.0011(13) C12 0.0183(16) 0.035(2) 0.034(2) 0.0098(17) 0.0101(15) 0.0084(14) C13 0.0236(17) 0.0276(18) 0.0339(19) 0.0037(16) 0.0169(16) 0.0067(14) C14 0.0218(16) 0.0177(15) 0.0251(17) 0.0039(13) 0.0133(14) 0.0034(12) C15 0.0359(19) 0.0183(16) 0.0257(17) 0.0003(14) 0.0194(16) 0.0049(14) C16 0.0341(19) 0.0197(16) 0.0191(16) -0.0024(13) 0.0136(14) -0.0023(14) C17 0.0235(16) 0.0173(15) 0.0145(14) 0.0041(12) 0.0072(13) -0.0005(12) C18 0.0180(14) 0.0128(14) 0.0153(14) 0.0030(12) 0.0079(12) 0.0005(11) C19 0.0198(15) 0.0149(15) 0.0167(14) 0.0023(12) 0.0091(12) 0.0002(12) C20 0.0195(17) 0.042(2) 0.030(2) 0.0001(17) -0.0001(15) 0.0010(15) C21 0.199(11) 0.058(4) 0.221(12) -0.057(6) 0.162(10) -0.041(5) C22 0.168(9) 0.081(5) 0.074(5) -0.015(4) 0.005(6) 0.017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O1 2.160(2) . ? Gd1 O2 2.328(2) 3 ? Gd1 O2 2.378(2) . ? Gd1 Cl2 2.6441(10) . ? Gd1 Cl1 2.6550(13) . ? Gd1 Cl3 2.6999(13) . ? Gd1 Gd1 3.8832(6) 3 ? N1 C1 1.347(6) . ? N1 C9 1.361(6) . ? N1 H1 0.8600 . ? N2 C11 1.332(4) . ? N2 C19 1.371(4) . ? N2 H2 0.8600 . ? O1 C8 1.318(4) . ? O2 C18 1.346(4) . ? O2 Gd1 2.328(2) 3 ? O3 C21 1.498(11) . ? O3 H99 0.852(10) . ? C1 C2 1.400(7) . ? C1 C10 1.481(8) . ? C2 C3 1.345(10) . ? C2 H2A 0.9300 . ? C3 C4 1.433(9) . ? C3 H3A 0.9300 . ? C4 C5 1.390(9) . ? C4 C9 1.416(5) . ? C5 C6 1.368(10) . ? C5 H5 0.9300 . ? C6 C7 1.429(6) . ? C6 H6 0.9300 . ? C7 C8 1.385(6) . ? C7 H7 0.9300 . ? C8 C9 1.420(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.412(5) . ? C11 C20 1.489(5) . ? C12 C13 1.365(6) . ? C12 H12 0.9300 . ? C13 C14 1.412(5) . ? C13 H13 0.9300 . ? C14 C15 1.411(5) . ? C14 C19 1.416(4) . ? C15 C16 1.367(5) . ? C15 H15 0.9300 . ? C16 C17 1.419(5) . ? C16 H16 0.9300 . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 C19 1.413(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.419(13) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Gd1 O2 154.91(8) . 3 ? O1 Gd1 O2 86.54(8) . . ? O2 Gd1 O2 68.79(8) 3 . ? O1 Gd1 Cl2 107.86(6) . . ? O2 Gd1 Cl2 96.29(5) 3 . ? O2 Gd1 Cl2 164.41(5) . . ? O1 Gd1 Cl1 90.87(7) . . ? O2 Gd1 Cl1 93.90(6) 3 . ? O2 Gd1 Cl1 90.91(6) . . ? Cl2 Gd1 Cl1 94.72(3) . . ? O1 Gd1 Cl3 86.59(7) . . ? O2 Gd1 Cl3 87.09(6) 3 . ? O2 Gd1 Cl3 85.76(6) . . ? Cl2 Gd1 Cl3 89.09(3) . . ? Cl1 Gd1 Cl3 175.92(3) . . ? O1 Gd1 Gd1 120.39(6) . 3 ? O2 Gd1 Gd1 34.82(5) 3 3 ? O2 Gd1 Gd1 33.98(5) . 3 ? Cl2 Gd1 Gd1 130.96(2) . 3 ? Cl1 Gd1 Gd1 92.90(3) . 3 ? Cl3 Gd1 Gd1 85.65(2) . 3 ? C1 N1 C9 125.2(4) . . ? C1 N1 H1 117.4 . . ? C9 N1 H1 117.4 . . ? C11 N2 C19 123.9(3) . . ? C11 N2 H2 118.0 . . ? C19 N2 H2 118.0 . . ? C8 O1 Gd1 162.8(2) . . ? C18 O2 Gd1 126.37(18) . 3 ? C18 O2 Gd1 121.52(18) . . ? Gd1 O2 Gd1 111.21(8) 3 . ? C21 O3 H99 113.1(16) . . ? N1 C1 C2 116.8(6) . . ? N1 C1 C10 119.7(4) . . ? C2 C1 C10 123.5(5) . . ? C3 C2 C1 121.2(6) . . ? C3 C2 H2A 119.4 . . ? C1 C2 H2A 119.4 . . ? C2 C3 C4 121.7(4) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C9 118.2(5) . . ? C5 C4 C3 125.7(5) . . ? C9 C4 C3 116.2(6) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 122.2(5) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C8 C7 C6 119.3(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? O1 C8 C7 124.0(4) . . ? O1 C8 C9 118.3(4) . . ? C7 C8 C9 117.7(4) . . ? N1 C9 C4 118.8(5) . . ? N1 C9 C8 118.6(3) . . ? C4 C9 C8 122.5(5) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 117.8(3) . . ? N2 C11 C20 117.9(3) . . ? C12 C11 C20 124.2(3) . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 124.8(3) . . ? C15 C14 C19 118.5(3) . . ? C13 C14 C19 116.6(3) . . ? C16 C15 C14 119.5(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 121.6(3) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? O2 C18 C17 124.4(3) . . ? O2 C18 C19 118.0(3) . . ? C17 C18 C19 117.6(3) . . ? N2 C19 C18 118.3(3) . . ? N2 C19 C14 119.6(3) . . ? C18 C19 C14 122.0(3) . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 O3 108.0(7) . . ? C22 C21 H21A 110.1 . . ? O3 C21 H21A 110.1 . . ? C22 C21 H21B 110.1 . . ? O3 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 H1 Cl3 0.86 2.49 3.325(3) 162.4 . N2 H2 Cl1 0.86 2.75 3.373(3) 130.5 . N2 H2 Cl3 0.86 2.89 3.609(3) 142.6 3 O3 H99 Cl1 0.852(10) 2.67(3) 3.413(5) 147(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.354 _refine_diff_density_min -1.466 _refine_diff_density_rms 0.109 #======================END _database_code_depnum_ccdc_archive 'CCDC 923353'