Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' #============================================================================== # SUBMISSION DETAILS _journal_coden_Cambridge 0222 _publ_contact_author_name 'David Parker' _publ_contact_author_address ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; _publ_contact_author_email David.Parker@durham.ac.uk _publ_contact_author_phone '0191 334 2033' _publ_contact_author_fax '0191 384 4737' #============================================================================== # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address P.A.Stenson ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; A.L.Thompson ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; D.Parker ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; _publ_section_title ; Structural characterisation of a diprotonated ligand lanthanide complex - A key intermediate in lanthanide ion association and complex dissociation pathways ; _publ_section_abstract ; The X-ray structure is reported of a diprotonated Gd(III) complex of the ligand 1,4,7,10-tetrakis(carbamoylmethyl)-1,4,7, 10-tetraazacyclododecane (DOTAM), the putative key intermediate in metal ion association and dissociation pathways. ; #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 605527' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetra-aqua-(1,4,7,10-terakis(carbamoylmethyl)- 1,7-diaza-4,10-diazoniumcyclodecane)-gadolinium penta-perchlorate trihydrate ; _chemical_name_common ; Tetra-aqua-(1,4,7,10-terakis(carbamoylmethyl)-1,7-diaza-4,10- diazoniumcyclodecane)-gadolinium penta-perchlorate trihydrate ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C16 H42 Gd N8 O8, 5(Cl O4), 3(H2 O)' _chemical_formula_sum 'C16 H48 Cl5 Gd N8 O31' _chemical_formula_weight 1183.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/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 11.2765(5) _cell_length_b 18.3391(7) _cell_length_c 19.7210(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.0440(10) _cell_angle_gamma 90.00 _cell_volume 4068.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7865 _cell_measurement_theta_min 2.350 _cell_measurement_theta_max 29.077 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2388 _exptl_absorpt_coefficient_mu 2.072 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6733 _exptl_absorpt_correction_T_max 0.8854 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.1400 -1.00 0.00 0.00 0.1400 0.00 1.00 0.00 0.0600 0.00 -1.00 0.00 0.0600 0.00 0.00 1.00 0.0300 0.00 0.00 -1.00 0.0300 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (20s exposure) covering 0.3\% in \w. Crystal to detector distance 4.45 cm. ; _diffrn_ambient_temperature 120(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 SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 47754 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 29.13 _reflns_number_total 10883 _reflns_number_gt 9166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V6.1 (Bruker, 2000)' _computing_cell_refinement 'SMART-NT V6.1 (Bruker, 2000)' _computing_data_reduction 'SAINT-NT V6.45A (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0280P)^2^+8.4630P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10883 _refine_ls_number_parameters 678 _refine_ls_number_restraints 106 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.068 _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 Gd1 Gd 0.709186(13) -0.144892(8) 0.337928(7) 0.01467(4) Uani 1 1 d . . . O1 O 0.71806(19) -0.17227(13) 0.45393(10) 0.0212(4) Uani 1 1 d . . . O2 O 0.53199(19) -0.20761(12) 0.35763(11) 0.0199(4) Uani 1 1 d . . . O3 O 0.6949(2) -0.23779(12) 0.25606(11) 0.0220(5) Uani 1 1 d . . . O4 O 0.87721(18) -0.22126(12) 0.36257(10) 0.0171(4) Uani 1 1 d . . . N1 N 0.6380(2) -0.31008(14) 0.49259(14) 0.0203(5) Uani 1 1 d . . . N2 N 0.5080(2) -0.35160(15) 0.36533(15) 0.0221(5) Uani 1 1 d D . . H2N H 0.567(3) -0.326(2) 0.3714(19) 0.027 Uiso 1 1 d D . . N3 N 0.7474(2) -0.37616(13) 0.31357(12) 0.0148(5) Uani 1 1 d . . . N4 N 0.8750(2) -0.33758(14) 0.44417(12) 0.0159(5) Uani 1 1 d D A . H4N H 0.818(3) -0.3176(19) 0.4240(17) 0.019 Uiso 1 1 d D . . N5 N 0.6653(3) -0.12647(16) 0.55266(15) 0.0262(6) Uani 1 1 d D . . H5NA H 0.700(3) -0.0895(14) 0.5435(18) 0.031 Uiso 1 1 d D . . H5NB H 0.627(3) -0.1302(19) 0.5857(14) 0.031 Uiso 1 1 d D . . N6 N 0.3403(4) -0.1906(2) 0.3211(3) 0.0245(9) Uani 0.70 1 d PD A 1 H6NA H 0.348(4) -0.1478(12) 0.330(3) 0.029 Uiso 0.70 1 d PD B 1 H6NB H 0.277(2) -0.210(2) 0.315(3) 0.029 Uiso 0.70 1 d PD C 1 N6A N 0.3646(9) -0.1868(6) 0.2883(5) 0.022(2) Uiso 0.30 1 d P A 2 H6NC H 0.3653 -0.1410 0.2978 0.026 Uiso 0.30 1 calc PR A 2 H6ND H 0.3095 -0.2044 0.2607 0.026 Uiso 0.30 1 calc PR A 2 N7 N 0.7540(3) -0.27806(17) 0.15659(14) 0.0265(6) Uani 1 1 d D . . H7NA H 0.787(3) -0.3096(16) 0.1364(17) 0.032 Uiso 1 1 d D . . H7NB H 0.732(3) -0.2402(13) 0.1389(17) 0.032 Uiso 1 1 d D . . N8 N 1.0578(3) -0.18251(17) 0.40398(15) 0.0251(6) Uani 1 1 d D . . H8NA H 1.109(3) -0.187(2) 0.4340(15) 0.030 Uiso 1 1 d D . . H8NB H 1.060(3) -0.1523(17) 0.3743(15) 0.030 Uiso 1 1 d D . . C1 C 0.5508(3) -0.36975(18) 0.49009(19) 0.0286(7) Uani 1 1 d . . . H1A H 0.5139 -0.3719 0.5330 0.034 Uiso 1 1 calc R A . H1B H 0.5916 -0.4156 0.4841 0.034 Uiso 1 1 calc R . . C2 C 0.4552(3) -0.36025(19) 0.4330(2) 0.0296(7) Uani 1 1 d . . . H2A H 0.4031 -0.4024 0.4314 0.035 Uiso 1 1 calc R . . H2B H 0.4079 -0.3176 0.4419 0.035 Uiso 1 1 calc R . . C3 C 0.5480(3) -0.42355(16) 0.33780(18) 0.0220(6) Uani 1 1 d . . . H3A H 0.4797 -0.4494 0.3170 0.026 Uiso 1 1 calc R . . H3B H 0.5823 -0.4531 0.3749 0.026 Uiso 1 1 calc R . . C4 C 0.6387(3) -0.41292(17) 0.28582(16) 0.0206(6) Uani 1 1 d . . . H4A H 0.6597 -0.4601 0.2681 0.025 Uiso 1 1 calc R A . H4B H 0.6032 -0.3844 0.2483 0.025 Uiso 1 1 calc R . . C5 C 0.8252(3) -0.42836(16) 0.35301(15) 0.0181(6) Uani 1 1 d . . . H5A H 0.8595 -0.4620 0.3219 0.022 Uiso 1 1 calc R A . H5B H 0.7775 -0.4565 0.3826 0.022 Uiso 1 1 calc R . . C6 C 0.9249(3) -0.39100(17) 0.39569(15) 0.0186(6) Uani 1 1 d . A . H6A H 0.9721 -0.4273 0.4211 0.022 Uiso 1 1 calc R . . H6B H 0.9764 -0.3656 0.3662 0.022 Uiso 1 1 calc R . . C7 C 0.8306(3) -0.37525(18) 0.50547(15) 0.0224(6) Uani 1 1 d . A . H7A H 0.8973 -0.3859 0.5378 0.027 Uiso 1 1 calc R . . H7B H 0.7934 -0.4211 0.4917 0.027 Uiso 1 1 calc R . . C8 C 0.7419(3) -0.32803(19) 0.53909(16) 0.0239(7) Uani 1 1 d . . . H8A H 0.7153 -0.3533 0.5785 0.029 Uiso 1 1 calc R A . H8B H 0.7805 -0.2832 0.5547 0.029 Uiso 1 1 calc R . . C9 C 0.5831(3) -0.24220(17) 0.51619(17) 0.0220(6) Uani 1 1 d . . . H9A H 0.5697 -0.2467 0.5641 0.026 Uiso 1 1 calc R A . H9B H 0.5066 -0.2350 0.4914 0.026 Uiso 1 1 calc R . . C10 C 0.6612(3) -0.17701(17) 0.50584(15) 0.0184(6) Uani 1 1 d . . . C11 C 0.4213(5) -0.3122(3) 0.3212(4) 0.0181(11) Uani 0.70 1 d P A 1 H11A H 0.3416 -0.3287 0.3289 0.022 Uiso 0.70 1 calc PR A 1 H11B H 0.4354 -0.3212 0.2739 0.022 Uiso 0.70 1 calc PR A 1 C12 C 0.4328(4) -0.2318(3) 0.3364(3) 0.0163(10) Uani 0.70 1 d P A 1 C11A C 0.4364(14) -0.3113(9) 0.3023(7) 0.015(4) Uiso 0.30 1 d P A 2 H11C H 0.4707 -0.3235 0.2600 0.018 Uiso 0.30 1 calc PR A 2 H11D H 0.3536 -0.3262 0.2991 0.018 Uiso 0.30 1 calc PR A 2 C12A C 0.4463(11) -0.2291(7) 0.3158(6) 0.009(3) Uiso 0.30 1 d P A 2 C13 C 0.8109(3) -0.34766(16) 0.25692(14) 0.0183(6) Uani 1 1 d . . . H13A H 0.8190 -0.3861 0.2238 0.022 Uiso 1 1 calc R A . H13B H 0.8902 -0.3328 0.2737 0.022 Uiso 1 1 calc R . . C14 C 0.7477(3) -0.28349(16) 0.22254(15) 0.0189(6) Uani 1 1 d . A . C15 C 0.9622(3) -0.27894(18) 0.46295(15) 0.0202(6) Uani 1 1 d . . . H15A H 1.0406 -0.2999 0.4721 0.024 Uiso 1 1 calc R A . H15B H 0.9401 -0.2545 0.5038 0.024 Uiso 1 1 calc R . . C16 C 0.9645(3) -0.22423(16) 0.40502(14) 0.0166(6) Uani 1 1 d . A . O1W O 0.8527(2) -0.06473(13) 0.39772(12) 0.0245(5) Uani 1 1 d D . . H1WA H 0.876(4) -0.0262(12) 0.3932(18) 0.032 Uiso 1 1 d D . . H1WB H 0.866(4) -0.073(2) 0.4352(10) 0.032 Uiso 1 1 d D . . O2W O 0.6020(2) -0.03984(15) 0.36813(15) 0.0343(6) Uani 1 1 d D . . H2WA H 0.629(3) -0.0091(18) 0.390(2) 0.045 Uiso 1 1 d D . . H2WB H 0.5355(15) -0.032(2) 0.366(2) 0.045 Uiso 1 1 d D . . O3W O 0.5746(3) -0.10601(14) 0.24483(13) 0.0318(6) Uani 1 1 d D . . H3WA H 0.539(4) -0.0710(15) 0.239(2) 0.041 Uiso 1 1 d D . . H3WB H 0.567(4) -0.126(2) 0.2112(13) 0.041 Uiso 1 1 d D . . O4W O 0.8330(2) -0.09585(14) 0.25611(11) 0.0265(5) Uani 1 1 d D . . H4WA H 0.9000(15) -0.093(2) 0.2628(19) 0.034 Uiso 1 1 d D . . H4WB H 0.822(3) -0.099(2) 0.2178(9) 0.034 Uiso 1 1 d D . . O5W O 0.3606(3) -0.02669(16) 0.34460(15) 0.0389(7) Uani 1 1 d D . . H5WA H 0.329(4) 0.000(2) 0.3134(16) 0.058 Uiso 1 1 d D . . H5WB H 0.322(4) -0.026(3) 0.3802(14) 0.058 Uiso 1 1 d D . . O6W O 1.0690(2) -0.07708(15) 0.29038(14) 0.0339(6) Uani 1 1 d D . . H6WA H 1.115(3) -0.088(2) 0.2598(18) 0.051 Uiso 1 1 d D . . H6WB H 1.087(4) -0.0360(13) 0.308(2) 0.051 Uiso 1 1 d D . . O7W O 0.4497(4) -0.1884(2) 0.1532(2) 0.0670(10) Uani 1 1 d D . . H7WA H 0.384(3) -0.179(3) 0.172(3) 0.100 Uiso 1 1 d D . . H7WB H 0.453(5) -0.2354(8) 0.147(4) 0.100 Uiso 1 1 d D . . Cl1 Cl 0.28974(7) -0.00879(5) 0.17729(4) 0.02681(17) Uani 1 1 d . . . O11 O 0.2565(2) -0.08216(13) 0.19380(13) 0.0320(6) Uani 1 1 d . . . O12 O 0.2360(2) 0.04058(14) 0.22289(15) 0.0368(6) Uani 1 1 d . . . O13 O 0.2442(3) 0.0067(2) 0.10842(15) 0.0545(9) Uani 1 1 d . . . O14 O 0.4159(2) -0.00082(18) 0.18399(19) 0.0558(10) Uani 1 1 d . . . Cl2 Cl 0.67809(7) 0.10602(4) 0.49725(4) 0.02610(16) Uani 1 1 d . . . O21 O 0.7313(3) 0.17652(16) 0.50320(18) 0.0588(10) Uani 1 1 d . . . O22 O 0.5712(3) 0.1048(2) 0.53183(18) 0.0610(10) Uani 1 1 d . . . O23 O 0.7572(3) 0.05098(16) 0.52562(16) 0.0433(7) Uani 1 1 d . . . O24 O 0.6502(3) 0.09278(15) 0.42613(14) 0.0429(7) Uani 1 1 d . . . Cl3 Cl 0.60490(8) -0.22397(6) 0.71336(5) 0.0360(2) Uani 1 1 d . . . O31 O 0.7201(2) -0.23659(16) 0.68886(13) 0.0377(6) Uani 1 1 d . . . O32 O 0.5532(2) -0.16016(17) 0.68117(13) 0.0412(7) Uani 1 1 d . . . O33 O 0.5294(3) -0.2851(2) 0.6981(2) 0.0754(13) Uani 1 1 d . . . O34 O 0.6183(3) -0.2134(2) 0.78570(14) 0.0541(9) Uani 1 1 d . . . Cl4 Cl 0.72135(14) -0.09699(9) 0.05463(8) 0.0157(3) Uani 0.90 1 d PD D 1 O41 O 0.6131(2) -0.05947(14) 0.03559(13) 0.0304(5) Uani 0.90 1 d PD D 1 O42 O 0.7353(2) -0.16029(13) 0.01342(13) 0.0316(6) Uani 0.90 1 d PD D 1 O43 O 0.7224(3) -0.11819(17) 0.12530(13) 0.0344(7) Uani 0.90 1 d PD D 1 O44 O 0.8197(2) -0.04751(14) 0.04693(14) 0.0257(6) Uani 0.90 1 d PD D 1 Cl4A Cl 0.7004(12) -0.1097(7) 0.0637(7) 0.025(4) Uani 0.10 1 d PD E 2 O41A O 0.6131(2) -0.05947(14) 0.03559(13) 0.0304(5) Uani 0.10 1 d PD E 2 O42A O 0.7353(2) -0.16029(13) 0.01342(13) 0.0316(6) Uani 0.10 1 d PD E 2 O43A O 0.6247(15) -0.1544(10) 0.1016(9) 0.011(4) Uiso 0.10 1 d PD E 2 O44A O 0.8019(16) -0.0832(11) 0.1048(9) 0.014(4) Uiso 0.10 1 d PD E 2 Cl5 Cl 1.03164(7) 0.10218(4) 0.39309(4) 0.02337(15) Uani 1 1 d . . . O51 O 0.9110(2) 0.07777(14) 0.37982(13) 0.0309(6) Uani 1 1 d . F . O52 O 1.0469(6) 0.1619(4) 0.3464(4) 0.0477(18) Uani 0.50 1 d P F 1 O53 O 1.1169(8) 0.0452(5) 0.3740(4) 0.0387(19) Uani 0.50 1 d P F 1 O54 O 1.0592(7) 0.1218(3) 0.4594(3) 0.0291(14) Uani 0.50 1 d P F 1 O52A O 1.0373(8) 0.1805(4) 0.3910(7) 0.090(4) Uani 0.50 1 d P F 2 O53A O 1.1042(8) 0.0705(5) 0.3496(4) 0.0415(19) Uani 0.50 1 d P F 2 O54A O 1.0641(9) 0.0784(8) 0.4638(5) 0.090(4) Uani 0.50 1 d P F 2 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 0.01712(7) 0.01149(6) 0.01483(7) 0.00114(5) -0.00283(4) -0.00299(6) O1 0.0190(11) 0.0275(12) 0.0170(10) 0.0023(9) 0.0004(8) -0.0054(9) O2 0.0134(10) 0.0169(10) 0.0287(11) -0.0001(8) -0.0036(8) -0.0026(8) O3 0.0276(12) 0.0155(10) 0.0215(11) -0.0026(8) -0.0086(9) 0.0031(9) O4 0.0154(10) 0.0196(10) 0.0161(10) 0.0011(8) -0.0007(7) -0.0005(8) N1 0.0179(13) 0.0159(12) 0.0276(13) 0.0023(10) 0.0059(10) 0.0014(10) N2 0.0126(12) 0.0125(12) 0.0408(16) -0.0017(11) -0.0015(10) -0.0023(10) N3 0.0150(12) 0.0129(11) 0.0164(11) 0.0023(9) 0.0008(9) 0.0012(9) N4 0.0142(12) 0.0173(12) 0.0162(11) 0.0047(9) -0.0004(9) 0.0034(9) N5 0.0278(16) 0.0245(15) 0.0274(15) -0.0021(11) 0.0082(12) -0.0029(12) N6 0.019(2) 0.0170(19) 0.036(2) -0.0082(18) -0.0068(18) 0.0017(15) N7 0.0374(17) 0.0233(14) 0.0182(13) 0.0051(11) -0.0016(11) 0.0011(13) N8 0.0182(14) 0.0316(16) 0.0254(14) -0.0021(12) 0.0009(11) -0.0079(12) C1 0.0311(18) 0.0188(16) 0.0379(19) 0.0030(13) 0.0165(15) -0.0024(13) C2 0.0181(15) 0.0211(16) 0.051(2) -0.0038(15) 0.0108(14) -0.0069(13) C3 0.0151(15) 0.0110(13) 0.0396(18) -0.0018(12) -0.0006(12) -0.0007(11) C4 0.0217(16) 0.0146(14) 0.0246(15) -0.0026(11) -0.0048(12) -0.0009(12) C5 0.0174(14) 0.0154(14) 0.0216(14) 0.0036(11) 0.0012(11) 0.0005(11) C6 0.0156(14) 0.0214(15) 0.0188(14) 0.0024(11) 0.0016(11) 0.0052(12) C7 0.0263(16) 0.0238(16) 0.0175(14) 0.0098(11) 0.0049(12) 0.0078(13) C8 0.0281(17) 0.0263(16) 0.0179(14) 0.0076(12) 0.0064(12) 0.0086(14) C9 0.0187(15) 0.0206(15) 0.0275(16) 0.0025(12) 0.0079(12) 0.0018(12) C10 0.0157(14) 0.0198(15) 0.0195(14) 0.0039(11) -0.0016(11) 0.0031(11) C11 0.015(3) 0.014(2) 0.026(3) -0.004(2) 0.000(2) 0.0001(17) C12 0.014(2) 0.020(2) 0.015(3) -0.002(2) 0.0028(19) 0.0003(16) C13 0.0247(15) 0.0142(14) 0.0160(13) 0.0003(11) 0.0017(11) 0.0012(12) C14 0.0206(15) 0.0161(14) 0.0192(14) 0.0000(11) -0.0046(11) -0.0045(12) C15 0.0160(14) 0.0257(16) 0.0179(14) 0.0002(12) -0.0057(11) 0.0003(12) C16 0.0142(13) 0.0195(14) 0.0162(13) -0.0045(11) 0.0020(10) -0.0007(11) O1W 0.0292(13) 0.0225(12) 0.0213(11) -0.0016(9) -0.0010(9) -0.0121(10) O2W 0.0268(13) 0.0267(13) 0.0481(16) -0.0180(11) -0.0072(12) 0.0035(11) O3W 0.0400(15) 0.0229(13) 0.0305(13) 0.0011(10) -0.0123(11) 0.0143(11) O4W 0.0356(14) 0.0270(12) 0.0164(10) 0.0029(9) -0.0011(9) -0.0084(11) O5W 0.0415(17) 0.0326(15) 0.0408(16) -0.0038(12) -0.0117(12) 0.0100(12) O6W 0.0334(14) 0.0363(15) 0.0339(14) -0.0052(11) 0.0146(11) -0.0125(12) O7W 0.058(2) 0.073(3) 0.069(3) -0.018(2) 0.0019(19) -0.001(2) Cl1 0.0234(4) 0.0260(4) 0.0321(4) 0.0095(3) 0.0094(3) 0.0071(3) O11 0.0420(15) 0.0236(12) 0.0308(13) -0.0025(10) 0.0053(11) -0.0030(11) O12 0.0310(14) 0.0274(13) 0.0511(17) -0.0065(12) -0.0041(12) 0.0098(11) O13 0.063(2) 0.067(2) 0.0341(16) 0.0214(15) 0.0075(14) 0.0262(18) O14 0.0193(14) 0.056(2) 0.094(3) 0.0443(19) 0.0154(15) 0.0116(14) Cl2 0.0220(4) 0.0198(4) 0.0354(4) -0.0033(3) -0.0056(3) 0.0023(3) O21 0.075(2) 0.0300(16) 0.065(2) 0.0039(15) -0.0384(18) -0.0165(16) O22 0.0439(19) 0.081(3) 0.060(2) 0.0203(19) 0.0188(16) 0.0319(18) O23 0.0353(16) 0.0351(16) 0.0592(19) 0.0158(14) 0.0018(13) 0.0132(13) O24 0.061(2) 0.0301(14) 0.0363(15) -0.0004(12) -0.0067(13) -0.0130(14) Cl3 0.0213(4) 0.0547(6) 0.0310(4) 0.0195(4) -0.0043(3) -0.0001(4) O31 0.0258(13) 0.0530(18) 0.0341(14) 0.0083(12) 0.0007(11) 0.0131(13) O32 0.0339(15) 0.064(2) 0.0273(13) 0.0175(13) 0.0107(11) 0.0218(14) O33 0.051(2) 0.080(3) 0.091(3) 0.037(2) -0.030(2) -0.031(2) O34 0.0287(15) 0.108(3) 0.0256(14) 0.0235(16) 0.0029(11) 0.0055(17) Cl4 0.0168(5) 0.0154(5) 0.0149(5) -0.0018(4) 0.0006(4) 0.0003(5) O41 0.0256(13) 0.0311(13) 0.0331(13) -0.0005(10) -0.0074(10) 0.0053(11) O42 0.0324(14) 0.0241(13) 0.0395(14) -0.0169(10) 0.0097(11) -0.0064(10) O43 0.0455(18) 0.0388(16) 0.0185(13) 0.0077(11) -0.0005(12) 0.0004(14) O44 0.0207(13) 0.0226(13) 0.0344(14) -0.0068(11) 0.0066(10) -0.0059(10) Cl4A 0.028(7) 0.025(7) 0.023(6) -0.002(5) 0.012(4) -0.003(5) O41A 0.0256(13) 0.0311(13) 0.0331(13) -0.0005(10) -0.0074(10) 0.0053(11) O42A 0.0324(14) 0.0241(13) 0.0395(14) -0.0169(10) 0.0097(11) -0.0064(10) Cl5 0.0223(4) 0.0231(4) 0.0241(4) -0.0023(3) -0.0027(3) -0.0044(3) O51 0.0249(13) 0.0302(13) 0.0360(13) 0.0073(11) -0.0087(10) -0.0091(10) O52 0.049(4) 0.032(4) 0.059(4) 0.029(3) -0.016(3) -0.024(3) O53 0.028(3) 0.039(5) 0.048(5) -0.020(3) -0.006(3) 0.010(3) O54 0.035(3) 0.037(3) 0.015(3) -0.013(2) -0.002(2) -0.008(3) O52A 0.055(5) 0.029(4) 0.191(11) -0.054(6) 0.040(6) -0.023(3) O53A 0.039(4) 0.041(5) 0.045(5) -0.024(3) 0.014(4) -0.006(4) O54A 0.044(5) 0.195(13) 0.029(4) 0.021(7) -0.013(3) 0.004(8) _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 2.337(2) . ? Gd1 O3 2.345(2) . ? Gd1 O2 2.361(2) . ? Gd1 O2W 2.373(3) . ? Gd1 O4 2.379(2) . ? Gd1 O4W 2.383(2) . ? Gd1 O3W 2.407(2) . ? Gd1 O1W 2.429(2) . ? O1 C10 1.248(4) . ? O2 C12 1.248(5) . ? O2 C12A 1.288(13) . ? O3 C14 1.245(4) . ? O4 C16 1.248(3) . ? N1 C1 1.470(4) . ? N1 C8 1.473(4) . ? N1 C9 1.480(4) . ? N2 C11 1.455(6) . ? N2 C2 1.507(5) . ? N2 C3 1.508(4) . ? N2 C11A 1.613(16) . ? N2 H2N 0.82(3) . ? N3 C13 1.465(4) . ? N3 C4 1.471(4) . ? N3 C5 1.482(4) . ? N4 C15 1.486(4) . ? N4 C6 1.506(4) . ? N4 C7 1.508(4) . ? N4 H4N 0.82(3) . ? N5 C10 1.307(4) . ? N5 H5NA 0.808(16) . ? N5 H5NB 0.808(16) . ? N6 C12 1.306(6) . ? N6 H6NA 0.806(17) . ? N6 H6NB 0.806(17) . ? N6A C12A 1.295(16) . ? N6A H6NA 1.11(4) . ? N6A H6NB 1.23(4) . ? N6A H6NC 0.8600 . ? N6A H6ND 0.8600 . ? N7 C14 1.311(4) . ? N7 H7NA 0.809(16) . ? N7 H7NB 0.808(16) . ? N8 C16 1.302(4) . ? N8 H8NA 0.806(16) . ? N8 H8NB 0.808(16) . ? C1 C2 1.512(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.511(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.519(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.511(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.508(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.509(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11A C12A 1.53(2) . ? C11A H11C 0.9700 . ? C11A H11D 0.9700 . ? C13 C14 1.511(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 C16 1.522(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O1W H1WA 0.762(16) . ? O1W H1WB 0.760(16) . ? O2W H2WA 0.759(16) . ? O2W H2WB 0.760(16) . ? O3W H3WA 0.761(16) . ? O3W H3WB 0.759(16) . ? O4W H4WA 0.759(16) . ? O4W H4WB 0.759(16) . ? O5W H5WA 0.850(10) . ? O5W H5WB 0.853(10) . ? O6W H6WA 0.847(10) . ? O6W H6WB 0.847(10) . ? O7W H7WA 0.873(10) . ? O7W H7WB 0.871(10) . ? Cl1 O14 1.426(3) . ? Cl1 O12 1.440(3) . ? Cl1 O11 1.440(3) . ? Cl1 O13 1.446(3) . ? Cl2 O22 1.426(3) . ? Cl2 O21 1.427(3) . ? Cl2 O23 1.435(3) . ? Cl2 O24 1.436(3) . ? Cl3 O33 1.426(4) . ? Cl3 O32 1.435(3) . ? Cl3 O31 1.437(3) . ? Cl3 O34 1.437(3) . ? Cl4 O41 1.428(3) . ? Cl4 O42 1.432(3) . ? Cl4 O43 1.446(3) . ? Cl4 O44 1.450(3) . ? Cl4A O43A 1.431(13) . ? Cl4A O44A 1.441(13) . ? Cl5 O53A 1.357(9) . ? Cl5 O54 1.371(6) . ? Cl5 O51 1.438(2) . ? Cl5 O52A 1.439(7) . ? Cl5 O52 1.449(5) . ? Cl5 O54A 1.482(9) . ? Cl5 O53 1.487(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Gd1 O3 120.93(8) . . ? O1 Gd1 O2 73.30(7) . . ? O3 Gd1 O2 75.03(8) . . ? O1 Gd1 O2W 85.19(9) . . ? O3 Gd1 O2W 138.71(8) . . ? O2 Gd1 O2W 84.38(9) . . ? O1 Gd1 O4 72.24(7) . . ? O3 Gd1 O4 74.21(7) . . ? O2 Gd1 O4 110.53(7) . . ? O2W Gd1 O4 147.08(8) . . ? O1 Gd1 O4W 139.20(8) . . ? O3 Gd1 O4W 79.81(8) . . ? O2 Gd1 O4W 146.95(8) . . ? O2W Gd1 O4W 101.35(10) . . ? O4 Gd1 O4W 82.20(8) . . ? O1 Gd1 O3W 142.33(9) . . ? O3 Gd1 O3W 71.40(8) . . ? O2 Gd1 O3W 76.95(9) . . ? O2W Gd1 O3W 69.25(9) . . ? O4 Gd1 O3W 141.35(8) . . ? O4W Gd1 O3W 74.92(9) . . ? O1 Gd1 O1W 70.96(8) . . ? O3 Gd1 O1W 141.72(8) . . ? O2 Gd1 O1W 139.22(8) . . ? O2W Gd1 O1W 73.76(9) . . ? O4 Gd1 O1W 76.32(8) . . ? O4W Gd1 O1W 72.44(8) . . ? O3W Gd1 O1W 123.63(9) . . ? C10 O1 Gd1 145.9(2) . . ? C12 O2 Gd1 150.1(3) . . ? C12A O2 Gd1 130.5(5) . . ? C14 O3 Gd1 147.4(2) . . ? C16 O4 Gd1 137.93(19) . . ? C1 N1 C8 110.8(3) . . ? C1 N1 C9 110.1(2) . . ? C8 N1 C9 108.9(3) . . ? C11 N2 C2 107.0(4) . . ? C11 N2 C3 115.1(3) . . ? C2 N2 C3 111.9(3) . . ? C2 N2 C11A 121.5(6) . . ? C3 N2 C11A 105.7(6) . . ? C11 N2 H2N 108(3) . . ? C2 N2 H2N 107(3) . . ? C3 N2 H2N 107(3) . . ? C11A N2 H2N 102(3) . . ? C13 N3 C4 108.6(2) . . ? C13 N3 C5 109.1(2) . . ? C4 N3 C5 110.3(2) . . ? C15 N4 C6 111.0(2) . . ? C15 N4 C7 112.5(2) . . ? C6 N4 C7 111.8(2) . . ? C15 N4 H4N 106(3) . . ? C6 N4 H4N 108(3) . . ? C7 N4 H4N 107(3) . . ? C10 N5 H5NA 116(3) . . ? C10 N5 H5NB 121(3) . . ? H5NA N5 H5NB 123(3) . . ? C12 N6 H6NA 116(3) . . ? C12 N6 H6NB 118(3) . . ? H6NA N6 H6NB 124(3) . . ? C12A N6A H6NA 103(3) . . ? C12A N6A H6NB 101(2) . . ? H6NA N6A H6NB 75(2) . . ? C12A N6A H6NC 120.0 . . ? H6NB N6A H6NC 104.3 . . ? C12A N6A H6ND 120.0 . . ? H6NA N6A H6ND 123.8 . . ? H6NB N6A H6ND 64.3 . . ? H6NC N6A H6ND 120.0 . . ? C14 N7 H7NA 119(3) . . ? C14 N7 H7NB 117(3) . . ? H7NA N7 H7NB 123(3) . . ? C16 N8 H8NA 118(3) . . ? C16 N8 H8NB 119(3) . . ? H8NA N8 H8NB 123(3) . . ? N1 C1 C2 112.3(3) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? N2 C2 C1 111.5(3) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C4 111.4(2) . . ? N2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N3 C4 C3 113.1(3) . . ? N3 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? N3 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.8 . . ? N3 C5 C6 112.8(2) . . ? N3 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N3 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N4 C6 C5 110.5(2) . . ? N4 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N4 C7 C8 110.9(2) . . ? N4 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N1 C8 C7 112.2(3) . . ? N1 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N1 C9 C10 111.3(2) . . ? N1 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N1 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O1 C10 N5 122.4(3) . . ? O1 C10 C9 120.3(3) . . ? N5 C10 C9 117.3(3) . . ? N2 C11 C12 108.8(4) . . ? N2 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N2 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O2 C12 N6 123.7(4) . . ? O2 C12 C11 118.5(4) . . ? N6 C12 C11 117.6(4) . . ? C12A C11A N2 106.9(10) . . ? C12A C11A H11C 110.3 . . ? N2 C11A H11C 110.3 . . ? C12A C11A H11D 110.3 . . ? N2 C11A H11D 110.3 . . ? H11C C11A H11D 108.6 . . ? O2 C12A N6A 124.3(11) . . ? O2 C12A C11A 117.0(11) . . ? N6A C12A C11A 118.4(12) . . ? N3 C13 C14 112.3(2) . . ? N3 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N3 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? O3 C14 N7 122.5(3) . . ? O3 C14 C13 120.9(3) . . ? N7 C14 C13 116.6(3) . . ? N4 C15 C16 109.7(2) . . ? N4 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? N4 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? O4 C16 N8 124.3(3) . . ? O4 C16 C15 118.5(3) . . ? N8 C16 C15 117.1(3) . . ? Gd1 O1W H1WA 137(3) . . ? Gd1 O1W H1WB 115(3) . . ? H1WA O1W H1WB 105(3) . . ? Gd1 O2W H2WA 123(3) . . ? Gd1 O2W H2WB 130(3) . . ? H2WA O2W H2WB 105(3) . . ? Gd1 O3W H3WA 131(3) . . ? Gd1 O3W H3WB 123(3) . . ? H3WA O3W H3WB 105(3) . . ? Gd1 O4W H4WA 122(3) . . ? Gd1 O4W H4WB 126(3) . . ? H4WA O4W H4WB 106(3) . . ? H5WA O5W H5WB 112(2) . . ? H6WA O6W H6WB 111(2) . . ? H7WA O7W H7WB 108(2) . . ? O14 Cl1 O12 109.8(2) . . ? O14 Cl1 O11 110.40(17) . . ? O12 Cl1 O11 108.58(16) . . ? O14 Cl1 O13 110.6(2) . . ? O12 Cl1 O13 109.05(18) . . ? O11 Cl1 O13 108.36(19) . . ? O22 Cl2 O21 109.8(2) . . ? O22 Cl2 O23 109.02(19) . . ? O21 Cl2 O23 111.04(19) . . ? O22 Cl2 O24 109.3(2) . . ? O21 Cl2 O24 107.19(18) . . ? O23 Cl2 O24 110.44(19) . . ? O33 Cl3 O32 109.2(2) . . ? O33 Cl3 O31 110.1(2) . . ? O32 Cl3 O31 109.35(16) . . ? O33 Cl3 O34 109.6(2) . . ? O32 Cl3 O34 109.9(2) . . ? O31 Cl3 O34 108.72(16) . . ? O41 Cl4 O42 111.54(18) . . ? O41 Cl4 O43 109.37(19) . . ? O42 Cl4 O43 109.6(2) . . ? O41 Cl4 O44 108.49(18) . . ? O42 Cl4 O44 109.43(18) . . ? O43 Cl4 O44 108.36(19) . . ? O43A Cl4A O44A 112.2(14) . . ? O53A Cl5 O54 127.5(5) . . ? O53A Cl5 O51 110.9(4) . . ? O54 Cl5 O51 113.8(3) . . ? O53A Cl5 O52A 112.3(5) . . ? O54 Cl5 O52A 76.0(6) . . ? O51 Cl5 O52A 110.4(4) . . ? O53A Cl5 O52 79.5(5) . . ? O54 Cl5 O52 112.2(4) . . ? O51 Cl5 O52 105.8(3) . . ? O53A Cl5 O54A 110.4(6) . . ? O51 Cl5 O54A 104.3(4) . . ? O52A Cl5 O54A 108.2(8) . . ? O52 Cl5 O54A 142.0(6) . . ? O54 Cl5 O53 108.6(4) . . ? O51 Cl5 O53 110.8(4) . . ? O52A Cl5 O53 131.6(5) . . ? O52 Cl5 O53 105.2(5) . . ? O54A Cl5 O53 84.8(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Gd1 O1 C10 -98.8(4) . . . . ? O2 Gd1 O1 C10 -38.5(4) . . . . ? O2W Gd1 O1 C10 47.1(4) . . . . ? O4 Gd1 O1 C10 -157.2(4) . . . . ? O4W Gd1 O1 C10 148.9(4) . . . . ? O3W Gd1 O1 C10 0.8(4) . . . . ? O1W Gd1 O1 C10 121.6(4) . . . . ? O1 Gd1 O2 C12 176.3(6) . . . . ? O3 Gd1 O2 C12 -54.2(5) . . . . ? O2W Gd1 O2 C12 89.6(6) . . . . ? O4 Gd1 O2 C12 -120.6(5) . . . . ? O4W Gd1 O2 C12 -12.6(6) . . . . ? O3W Gd1 O2 C12 19.7(5) . . . . ? O1W Gd1 O2 C12 146.7(5) . . . . ? O1 Gd1 O2 C12A -175.7(8) . . . . ? O3 Gd1 O2 C12A -46.2(8) . . . . ? O2W Gd1 O2 C12A 97.6(8) . . . . ? O4 Gd1 O2 C12A -112.6(8) . . . . ? O4W Gd1 O2 C12A -4.6(8) . . . . ? O3W Gd1 O2 C12A 27.7(8) . . . . ? O1W Gd1 O2 C12A 154.7(8) . . . . ? O1 Gd1 O3 C14 -84.2(4) . . . . ? O2 Gd1 O3 C14 -143.7(4) . . . . ? O2W Gd1 O3 C14 153.6(4) . . . . ? O4 Gd1 O3 C14 -26.8(4) . . . . ? O4W Gd1 O3 C14 57.9(4) . . . . ? O3W Gd1 O3 C14 135.3(4) . . . . ? O1W Gd1 O3 C14 14.2(4) . . . . ? O1 Gd1 O4 C16 -49.2(3) . . . . ? O3 Gd1 O4 C16 -179.9(3) . . . . ? O2 Gd1 O4 C16 -113.0(3) . . . . ? O2W Gd1 O4 C16 -0.3(4) . . . . ? O4W Gd1 O4 C16 98.6(3) . . . . ? O3W Gd1 O4 C16 152.3(3) . . . . ? O1W Gd1 O4 C16 24.8(3) . . . . ? C8 N1 C1 C2 -168.6(3) . . . . ? C9 N1 C1 C2 70.9(3) . . . . ? C11 N2 C2 C1 -155.4(3) . . . . ? C3 N2 C2 C1 77.6(3) . . . . ? C11A N2 C2 C1 -156.3(7) . . . . ? N1 C1 C2 N2 55.1(4) . . . . ? C11 N2 C3 C4 78.6(4) . . . . ? C2 N2 C3 C4 -159.0(3) . . . . ? C11A N2 C3 C4 66.7(6) . . . . ? C13 N3 C4 C3 -161.9(2) . . . . ? C5 N3 C4 C3 78.5(3) . . . . ? N2 C3 C4 N3 60.9(3) . . . . ? C13 N3 C5 C6 73.5(3) . . . . ? C4 N3 C5 C6 -167.3(2) . . . . ? C15 N4 C6 C5 -154.5(2) . . . . ? C7 N4 C6 C5 79.0(3) . . . . ? N3 C5 C6 N4 58.1(3) . . . . ? C15 N4 C7 C8 75.7(3) . . . . ? C6 N4 C7 C8 -158.6(3) . . . . ? C1 N1 C8 C7 82.5(3) . . . . ? C9 N1 C8 C7 -156.3(3) . . . . ? N4 C7 C8 N1 59.3(4) . . . . ? C1 N1 C9 C10 -168.4(3) . . . . ? C8 N1 C9 C10 69.9(3) . . . . ? Gd1 O1 C10 N5 -101.3(4) . . . . ? Gd1 O1 C10 C9 78.0(5) . . . . ? N1 C9 C10 O1 38.1(4) . . . . ? N1 C9 C10 N5 -142.6(3) . . . . ? C2 N2 C11 C12 81.5(5) . . . . ? C3 N2 C11 C12 -153.4(4) . . . . ? C11A N2 C11 C12 -102(3) . . . . ? C12A O2 C12 N6 -90(2) . . . . ? Gd1 O2 C12 N6 -71.8(9) . . . . ? C12A O2 C12 C11 84(2) . . . . ? Gd1 O2 C12 C11 102.1(7) . . . . ? N2 C11 C12 O2 29.3(8) . . . . ? N2 C11 C12 N6 -156.4(5) . . . . ? C11 N2 C11A C12A 74(3) . . . . ? C2 N2 C11A C12A 77.7(10) . . . . ? C3 N2 C11A C12A -153.4(8) . . . . ? C12 O2 C12A N6A 91(2) . . . . ? Gd1 O2 C12A N6A -77.0(13) . . . . ? C12 O2 C12A C11A -84(2) . . . . ? Gd1 O2 C12A C11A 107.9(10) . . . . ? N2 C11A C12A O2 20.5(13) . . . . ? N2 C11A C12A N6A -154.9(10) . . . . ? C4 N3 C13 C14 71.0(3) . . . . ? C5 N3 C13 C14 -168.7(2) . . . . ? Gd1 O3 C14 N7 -111.9(4) . . . . ? Gd1 O3 C14 C13 66.6(5) . . . . ? N3 C13 C14 O3 36.5(4) . . . . ? N3 C13 C14 N7 -144.9(3) . . . . ? C6 N4 C15 C16 77.2(3) . . . . ? C7 N4 C15 C16 -156.7(2) . . . . ? Gd1 O4 C16 N8 -75.9(4) . . . . ? Gd1 O4 C16 C15 102.9(3) . . . . ? N4 C15 C16 O4 20.9(4) . . . . ? N4 C15 C16 N8 -160.3(3) . . . . ? 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 N2 H2N O2 0.82(3) 2.21(4) 2.660(3) 114(3) . N2 H2N N1 0.82(3) 2.48(4) 2.917(4) 114(3) . N2 H2N N3 0.82(3) 2.57(4) 2.987(4) 113(3) . N4 H4N O4 0.82(3) 2.27(4) 2.673(3) 111(3) . N4 H4N N3 0.82(3) 2.51(3) 2.946(3) 115(3) . N4 H4N N1 0.82(3) 2.52(3) 2.944(4) 114(3) . N5 H5NB O32 0.808(16) 2.183(19) 2.975(4) 167(4) . N6 H6NA O5W 0.806(17) 2.243(18) 3.047(5) 175(5) . N6 H6NB O34 0.806(17) 2.307(19) 3.099(5) 168(5) 4 N6 H6NB Cl3 0.806(17) 2.94(3) 3.636(4) 146(5) 4 N6A H6NC O5W 0.86 2.29 3.140(11) 168.5 . N6A H6ND O31 0.86 2.00 2.833(11) 163.5 4 N6A H6ND Cl3 0.86 2.76 3.582(10) 160.4 4 N7 H7NA O24 0.809(16) 2.313(18) 3.113(4) 170(4) 2_645 N7 H7NB O43A 0.808(16) 2.09(3) 2.867(18) 162(4) . N7 H7NB O43 0.808(16) 2.25(2) 3.012(4) 156(4) . N7 H7NB Cl4A 0.808(16) 2.83(2) 3.620(13) 168(3) . N8 H8NA O21 0.806(16) 2.12(2) 2.899(4) 163(3) 3_756 N8 H8NB O6W 0.808(16) 2.162(17) 2.969(4) 176(4) . O1W H1WA O51 0.762(16) 1.969(17) 2.724(3) 171(4) . O1W H1WA Cl5 0.762(16) 2.94(2) 3.671(2) 163(4) . O1W H1WB O54A 0.760(16) 2.09(2) 2.836(9) 166(4) 3_756 O1W H1WB O54 0.760(16) 2.36(2) 3.103(7) 165(4) 3_756 O2W H2WA O24 0.759(16) 2.01(2) 2.726(4) 157(4) . O2W H2WB O5W 0.760(16) 1.989(18) 2.739(4) 169(4) . O3W H3WA O14 0.761(16) 2.14(2) 2.839(4) 154(4) . O3W H3WB O7W 0.759(16) 2.04(3) 2.679(5) 143(5) . O3W H3WB O43A 0.759(16) 2.36(3) 3.052(18) 152(5) . O3W H3WB O43 0.759(16) 2.53(4) 2.990(4) 121(4) . O4W H4WA O6W 0.759(16) 1.967(17) 2.721(4) 172(4) . O4W H4WB O43 0.759(16) 2.10(2) 2.815(4) 156(4) . O4W H4WB O44A 0.759(16) 2.24(3) 2.988(18) 168(4) . O5W H5WA O12 0.850(10) 2.135(17) 2.963(4) 164(5) . O5W H5WA Cl1 0.850(10) 2.70(3) 3.356(3) 136(4) . O5W H5WB O23 0.853(10) 2.164(14) 2.999(4) 166(4) 3_656 O5W H5WB O53 0.853(10) 2.65(4) 3.138(9) 118(3) 1_455 O5W H5WB Cl2 0.853(10) 2.83(3) 3.497(3) 137(4) 3_656 O6W H6WA O11 0.847(10) 2.130(18) 2.945(4) 161(4) 1_655 O6W H6WB O53 0.847(10) 1.992(18) 2.813(9) 163(4) . O6W H6WB O53A 0.847(10) 2.123(14) 2.964(9) 172(4) . O7W H7WA N6A 0.873(10) 2.32(6) 2.897(11) 123(6) . O7W H7WA O11 0.873(10) 2.34(4) 3.071(5) 142(5) . O7W H7WA O31 0.873(10) 2.46(5) 3.057(5) 127(5) 4 O7W H7WB O52A 0.871(10) 1.72(3) 2.565(10) 162(7) 2_645 O7W H7WB O52 0.871(10) 1.89(2) 2.745(8) 168(6) 2_645 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.933 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.106