# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_contact_author_name 'Antonio Facchetti' _publ_contact_author_address ; Departmnent of Chemistry Northwestern University 2145 N Sheridan Road Evanston 60208 UNITED STATES OF AMERICA ; _publ_contact_author_email A-FACCHETTI@NORTHWESTERN.EDU _publ_section_title ; Novel coordinating motifs for lanthanide (III) ions based on 5-(2-pyridyl)-tetrazole and 5-(2-pyridyl-1-oxide)tetrazole. Potential new contrast agents ; loop_ _publ_author_name 'Antonio Facchetti' 'Alessandro Abbotto' 'Luca Beverina' 'Silva Bradamante' 'Palma mariani' ; T.Marks ; 'Giorgio A. Pagani' 'Charlotte L. Stern' 'Alberto Vacca' data_s71m--Zn2 _database_code_depnum_ccdc_archive 'CCDC 232481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N10 O6 Zn' _chemical_formula_weight 539.82 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.01(2) _cell_length_b 8.561(4) _cell_length_c 7.546(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.65(5) _cell_angle_gamma 90.00 _cell_volume 1968.8(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.244 _exptl_crystal_size_mid 0.218 _exptl_crystal_size_min 0.036 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7387 _exptl_absorpt_correction_T_max 0.9549 _exptl_absorpt_process_details ? _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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8819 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.87 _reflns_number_total 2401 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0575P)^2^+2.6307P] 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 2401 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 Zn1 Zn 0.0000 0.22400(6) 0.2500 0.01678(17) Uani 1 2 d S . . O1 O 0.04633(7) 0.0477(3) 0.3222(3) 0.0220(5) Uani 1 1 d . . . O2 O 0.00979(8) 0.2146(3) -0.0257(3) 0.0238(5) Uani 1 1 d . . . H02A H 0.0187(13) 0.297(4) -0.059(5) 0.029 Uiso 1 1 d . . . H02B H 0.0211(12) 0.141(5) -0.059(5) 0.029 Uiso 1 1 d . . . N1 N 0.08516(8) 0.0440(3) 0.2697(3) 0.0178(6) Uani 1 1 d . . . N2 N 0.12182(9) 0.4435(3) 0.3702(4) 0.0244(6) Uani 1 1 d . . . N3 N 0.09651(9) 0.5618(3) 0.4040(4) 0.0258(6) Uani 1 1 d . . . N4 N 0.05493(9) 0.5193(3) 0.3710(4) 0.0224(6) Uani 1 1 d . . . N5 N 0.05266(8) 0.3704(3) 0.3174(3) 0.0183(6) Uani 1 1 d . . . C1 C 0.10025(11) -0.0964(4) 0.2301(4) 0.0245(7) Uani 1 1 d . . . H1 H 0.0827 -0.1844 0.2316 0.029 Uiso 1 1 calc R . . C2 C 0.14105(11) -0.1116(4) 0.1876(4) 0.0281(8) Uani 1 1 d . . . H2 H 0.1518 -0.2101 0.1670 0.034 Uiso 1 1 calc R . . C3 C 0.16632(11) 0.0192(4) 0.1754(5) 0.0292(8) Uani 1 1 d . . . H3 H 0.1938 0.0105 0.1435 0.035 Uiso 1 1 calc R . . C4 C 0.14988(11) 0.1634(4) 0.2115(4) 0.0236(7) Uani 1 1 d . . . H4 H 0.1662 0.2530 0.2012 0.028 Uiso 1 1 calc R . . C5 C 0.10907(10) 0.1758(4) 0.2634(4) 0.0190(6) Uani 1 1 d . . . C6 C 0.09398(10) 0.3269(4) 0.3163(4) 0.0179(6) Uani 1 1 d . . . O3 O 0.21077(16) 0.5210(6) 0.3893(7) 0.0351(9) Uani 0.500(4) 1 d P . . O4 O 0.21086(16) 0.4702(6) 0.5315(7) 0.0351(9) Uani 0.500(4) 1 d P . . O5 O 0.2360(2) 0.7507(7) 0.0754(9) 0.0535(16) Uani 0.50 1 d P . . O6 O 0.2489(3) 0.7335(9) 0.4360(10) 0.066(2) Uani 0.50 1 d P . . 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 Zn1 0.0184(3) 0.0133(3) 0.0193(3) 0.000 0.00534(19) 0.000 O1 0.0203(12) 0.0195(12) 0.0284(12) 0.0031(9) 0.0101(9) 0.0015(9) O2 0.0346(14) 0.0149(11) 0.0248(12) -0.0025(10) 0.0134(10) -0.0029(10) N1 0.0207(14) 0.0152(13) 0.0180(13) 0.0006(10) 0.0054(10) 0.0026(10) N2 0.0257(15) 0.0204(15) 0.0266(15) -0.0033(11) 0.0035(12) -0.0027(11) N3 0.0275(16) 0.0180(14) 0.0306(16) -0.0038(12) 0.0025(12) -0.0020(12) N4 0.0286(15) 0.0138(13) 0.0253(15) -0.0014(11) 0.0064(11) -0.0002(11) N5 0.0214(14) 0.0153(13) 0.0192(13) -0.0006(10) 0.0059(10) 0.0002(10) C1 0.0324(19) 0.0185(16) 0.0223(17) -0.0006(13) 0.0040(14) 0.0032(14) C2 0.0331(19) 0.0272(19) 0.0239(17) -0.0049(14) 0.0051(14) 0.0113(15) C3 0.0247(18) 0.039(2) 0.0251(18) -0.0061(15) 0.0063(14) 0.0029(15) C4 0.0213(17) 0.0289(17) 0.0215(16) -0.0016(14) 0.0059(13) 0.0001(14) C5 0.0192(16) 0.0214(16) 0.0166(15) 0.0005(12) 0.0036(12) 0.0007(12) C6 0.0195(16) 0.0178(15) 0.0170(15) 0.0008(12) 0.0044(12) 0.0002(12) O3 0.0289(19) 0.038(2) 0.037(2) -0.0015(17) 0.0025(17) -0.0055(16) O4 0.0289(19) 0.038(2) 0.037(2) -0.0015(17) 0.0025(17) -0.0055(16) O5 0.053(4) 0.049(4) 0.057(4) 0.000(3) 0.007(3) -0.006(3) O6 0.079(5) 0.058(4) 0.059(5) -0.012(4) 0.007(5) -0.023(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N5 2.046(3) . ? Zn1 N5 2.046(3) 2 ? Zn1 O1 2.086(2) 2 ? Zn1 O1 2.086(2) . ? Zn1 O2 2.159(2) . ? Zn1 O2 2.159(2) 2 ? O1 N1 1.336(3) . ? O2 H02A 0.82(4) . ? O2 H02B 0.79(4) . ? N1 C1 1.343(4) . ? N1 C5 1.356(4) . ? N2 C6 1.333(4) . ? N2 N3 1.335(4) . ? N3 N4 1.319(4) . ? N4 N5 1.335(4) . ? N5 C6 1.336(4) . ? C1 C2 1.367(5) . ? C1 H1 0.9300 . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.382(5) . ? C3 H3 0.9300 . ? C4 C5 1.396(4) . ? C4 H4 0.9300 . ? C5 C6 1.456(4) . ? O3 O4 1.158(7) . ? O5 O5 1.554(14) 7_565 ? O6 O6 0.997(13) 7_566 ? 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 N5 Zn1 N5 104.50(15) . 2 ? N5 Zn1 O1 170.94(9) . 2 ? N5 Zn1 O1 84.18(10) 2 2 ? N5 Zn1 O1 84.18(10) . . ? N5 Zn1 O1 170.94(9) 2 . ? O1 Zn1 O1 87.29(13) 2 . ? N5 Zn1 O2 90.83(10) . . ? N5 Zn1 O2 91.79(11) 2 . ? O1 Zn1 O2 86.21(10) 2 . ? O1 Zn1 O2 90.69(10) . . ? N5 Zn1 O2 91.79(11) . 2 ? N5 Zn1 O2 90.83(10) 2 2 ? O1 Zn1 O2 90.69(10) 2 2 ? O1 Zn1 O2 86.21(10) . 2 ? O2 Zn1 O2 175.72(14) . 2 ? N1 O1 Zn1 123.70(17) . . ? Zn1 O2 H02A 113(3) . . ? Zn1 O2 H02B 119(3) . . ? H02A O2 H02B 114(4) . . ? O1 N1 C1 117.2(3) . . ? O1 N1 C5 121.3(2) . . ? C1 N1 C5 121.4(3) . . ? C6 N2 N3 104.8(3) . . ? N4 N3 N2 110.1(3) . . ? N3 N4 N5 108.4(3) . . ? N4 N5 C6 105.7(3) . . ? N4 N5 Zn1 130.9(2) . . ? C6 N5 Zn1 123.4(2) . . ? N1 C1 C2 120.8(3) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N1 C5 C4 118.4(3) . . ? N1 C5 C6 121.6(3) . . ? C4 C5 C6 119.9(3) . . ? N2 C6 N5 110.9(3) . . ? N2 C6 C5 121.7(3) . . ? N5 C6 C5 127.3(3) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 28.87 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.784 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.112 data_s72m1m _database_code_depnum_ccdc_archive 'CCDC 232482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 Gd N15 O10' _chemical_formula_weight 769.74 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 7.847(3) _cell_length_b 39.783(7) _cell_length_c 9.092(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.50(3) _cell_angle_gamma 90.00 _cell_volume 2820.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.238 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 2.430 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3687 _exptl_absorpt_correction_T_max 0.8277 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18878 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.48 _reflns_number_total 5168 _reflns_number_gt 4808 _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 '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^)+(0.0000P)^2^+75.3126P] 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 SHELXL _refine_ls_extinction_coef 0.0014(2) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5168 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 1.337 _refine_ls_restrained_S_all 1.337 _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 0.19250(7) 0.151966(13) 0.91694(6) 0.0150(2) Uani 1 1 d . . . O1 O -0.0982(9) 0.14341(19) 0.8386(8) 0.0193(16) Uani 1 1 d . . . O2 O 0.2219(9) 0.09710(19) 0.8233(8) 0.0185(16) Uani 1 1 d . . . O3 O 0.4369(9) 0.1791(2) 0.8682(8) 0.0206(17) Uani 1 1 d . . . O4 O 0.2386(9) 0.19069(19) 1.1272(8) 0.0191(16) Uani 1 1 d . . . O5 O 0.0722(9) 0.1212(2) 1.1052(8) 0.0185(16) Uani 1 1 d . . . O6 O 0.6441(12) 0.0077(2) 0.9305(11) 0.038(2) Uani 1 1 d . . . O7 O 0.5181(11) 0.0620(2) 0.7554(11) 0.036(2) Uani 1 1 d . . . O8 O 0.3796(15) 0.0259(3) 0.5039(13) 0.059(3) Uani 1 1 d . . . O9 O 0.2366(12) 0.0466(2) 0.2173(11) 0.036(2) Uani 1 1 d . . . O10 O 0.8854(12) 0.0365(3) 0.1363(12) 0.045(3) Uani 1 1 d . . . N1 N -0.1962(10) 0.1522(2) 0.7161(9) 0.0156(18) Uani 1 1 d . . . N2 N -0.1206(11) 0.2426(2) 0.7094(10) 0.0163(19) Uani 1 1 d . . . N3 N 0.0039(12) 0.2583(2) 0.7967(11) 0.022(2) Uani 1 1 d . . . N4 N 0.1082(13) 0.2363(3) 0.8667(11) 0.025(2) Uani 1 1 d . . . N5 N 0.0528(11) 0.2054(2) 0.8300(9) 0.0161(19) Uani 1 1 d . . . N6 N 0.1117(12) 0.0805(2) 0.7260(10) 0.0188(19) Uani 1 1 d . . . N7 N 0.1417(12) 0.1340(2) 0.4043(10) 0.020(2) Uani 1 1 d . . . N8 N 0.1889(12) 0.1664(2) 0.4080(10) 0.0201(19) Uani 1 1 d . . . N9 N 0.2121(11) 0.1769(2) 0.5468(9) 0.0164(19) Uani 1 1 d . . . N10 N 0.1774(11) 0.1513(2) 0.6379(10) 0.0170(18) Uani 1 1 d . . . N11 N 0.5629(11) 0.1927(2) 0.9597(10) 0.019(2) Uani 1 1 d . . . N12 N 0.4515(11) 0.1261(2) 1.0681(10) 0.0175(19) Uani 1 1 d . . . N13 N 0.4687(11) 0.0943(2) 1.1181(11) 0.022(2) Uani 1 1 d . . . N14 N 0.6328(12) 0.0882(3) 1.1594(12) 0.026(2) Uani 1 1 d . . . N15 N 0.7253(12) 0.1161(2) 1.1395(11) 0.022(2) Uani 1 1 d . . . C1 C -0.3008(13) 0.1280(3) 0.6503(12) 0.019(2) Uani 1 1 d . . . H1 H -0.3031 0.1064 0.6942 0.023 Uiso 1 1 calc R . . C2 C -0.4025(14) 0.1345(3) 0.5219(13) 0.023(2) Uani 1 1 d . . . H2 H -0.4756 0.1175 0.4765 0.027 Uiso 1 1 calc R . . C3 C -0.3983(14) 0.1661(3) 0.4581(13) 0.023(2) Uani 1 1 d . . . H3 H -0.4653 0.1707 0.3667 0.027 Uiso 1 1 calc R . . C4 C -0.2965(14) 0.1905(3) 0.5285(12) 0.022(2) Uani 1 1 d . . . H4 H -0.2961 0.2125 0.4871 0.026 Uiso 1 1 calc R . . C5 C -0.1932(13) 0.1835(3) 0.6607(11) 0.015(2) Uani 1 1 d . . . C6 C -0.0878(13) 0.2097(3) 0.7338(11) 0.013(2) Uani 1 1 d . . . C7 C 0.0534(17) 0.0509(3) 0.7679(14) 0.030(3) Uani 1 1 d . . . H7 H 0.0877 0.0428 0.8650 0.036 Uiso 1 1 calc R . . C8 C -0.0571(17) 0.0319(3) 0.6712(15) 0.033(3) Uani 1 1 d . . . H8 H -0.1017 0.0112 0.7026 0.040 Uiso 1 1 calc R . . C9 C -0.1007(16) 0.0433(3) 0.5307(14) 0.029(3) Uani 1 1 d . . . H9 H -0.1740 0.0304 0.4621 0.035 Uiso 1 1 calc R . . C17 C 0.6574(13) 0.1734(3) 1.0591(12) 0.019(2) Uani 1 1 d . . . C10 C -0.0372(15) 0.0739(3) 0.4887(13) 0.023(2) Uani 1 1 d . . . H10 H -0.0678 0.0820 0.3910 0.028 Uiso 1 1 calc R . . C11 C 0.0697(15) 0.0926(3) 0.5872(12) 0.022(2) Uani 1 1 d . . . C12 C 0.1354(13) 0.1251(3) 0.5448(11) 0.015(2) Uani 1 1 d . . . C13 C 0.5947(16) 0.2257(3) 0.9448(14) 0.025(3) Uani 1 1 d . . . H13 H 0.5210 0.2387 0.8770 0.030 Uiso 1 1 calc R . . C14 C 0.7323(16) 0.2408(3) 1.0261(15) 0.030(3) Uani 1 1 d . . . H14 H 0.7536 0.2641 1.0167 0.036 Uiso 1 1 calc R . . C15 C 0.8379(15) 0.2211(3) 1.1209(13) 0.026(3) Uani 1 1 d . . . H15 H 0.9376 0.2306 1.1743 0.031 Uiso 1 1 calc R . . C16 C 0.7999(14) 0.1881(3) 1.1387(13) 0.024(3) Uani 1 1 d . . . H16 H 0.8720 0.1748 1.2068 0.029 Uiso 1 1 calc R . . C18 C 0.6115(12) 0.1390(3) 1.0828(12) 0.017(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.0137(3) 0.0209(3) 0.0104(3) 0.0010(2) 0.00134(17) 0.0008(2) O1 0.015(4) 0.025(4) 0.017(4) 0.004(3) -0.002(3) 0.002(3) O2 0.021(4) 0.021(4) 0.012(4) 0.002(3) -0.003(3) 0.000(3) O3 0.015(4) 0.033(4) 0.013(4) 0.005(3) -0.001(3) -0.006(3) O4 0.020(4) 0.025(4) 0.011(4) 0.000(3) -0.002(3) 0.000(3) O5 0.010(3) 0.032(4) 0.014(4) 0.004(3) 0.005(3) 0.000(3) O6 0.032(5) 0.046(6) 0.034(5) -0.005(4) 0.003(4) -0.002(4) O7 0.030(5) 0.031(5) 0.047(6) -0.003(4) 0.010(4) 0.002(4) O8 0.062(8) 0.067(8) 0.046(7) -0.007(6) -0.003(6) 0.009(6) O9 0.033(5) 0.032(5) 0.046(6) 0.003(4) 0.011(4) 0.000(4) O10 0.031(5) 0.046(6) 0.054(7) -0.009(5) -0.004(5) 0.009(4) N1 0.010(4) 0.028(5) 0.009(4) 0.002(4) 0.000(3) 0.003(4) N2 0.017(4) 0.018(5) 0.014(5) 0.000(4) 0.000(4) 0.001(4) N3 0.021(5) 0.020(5) 0.026(5) -0.003(4) 0.000(4) -0.001(4) N4 0.027(5) 0.025(5) 0.024(5) -0.003(4) 0.007(4) -0.002(4) N5 0.018(4) 0.022(5) 0.009(4) 0.002(4) 0.002(4) 0.002(4) N6 0.020(5) 0.024(5) 0.013(5) 0.000(4) 0.006(4) 0.001(4) N7 0.024(5) 0.024(5) 0.010(4) 0.000(4) -0.002(4) -0.005(4) N8 0.021(4) 0.033(5) 0.007(4) 0.000(4) 0.004(3) -0.002(4) N9 0.021(5) 0.018(5) 0.010(5) 0.006(4) 0.003(4) -0.004(4) N10 0.020(4) 0.017(4) 0.014(4) 0.002(4) 0.002(4) 0.000(4) N11 0.017(5) 0.028(5) 0.014(5) 0.001(4) 0.009(4) 0.002(4) N12 0.011(4) 0.021(5) 0.020(5) 0.004(4) 0.000(4) -0.002(4) N13 0.013(4) 0.023(5) 0.027(5) 0.007(4) -0.004(4) -0.004(4) N14 0.017(5) 0.029(6) 0.031(6) 0.004(4) -0.004(4) 0.002(4) N15 0.018(5) 0.025(5) 0.021(5) 0.006(4) -0.002(4) 0.001(4) C1 0.018(5) 0.022(6) 0.017(6) -0.004(4) 0.005(4) -0.001(4) C2 0.019(5) 0.025(6) 0.024(6) -0.008(5) 0.002(5) -0.002(5) C3 0.015(5) 0.036(7) 0.016(6) -0.003(5) -0.002(4) 0.001(5) C4 0.021(6) 0.028(6) 0.016(6) -0.002(5) 0.002(4) 0.002(5) C5 0.013(5) 0.020(5) 0.012(5) -0.005(4) 0.004(4) 0.001(4) C6 0.013(5) 0.018(5) 0.008(5) -0.002(4) 0.004(4) 0.004(4) C7 0.043(8) 0.022(6) 0.026(7) 0.006(5) 0.004(6) 0.002(5) C8 0.041(8) 0.023(6) 0.037(8) 0.001(6) 0.007(6) -0.008(6) C9 0.027(6) 0.030(7) 0.030(7) -0.005(5) 0.001(5) -0.004(5) C17 0.015(5) 0.032(6) 0.012(5) -0.002(4) 0.007(4) 0.006(5) C10 0.025(6) 0.028(6) 0.017(6) -0.007(5) -0.002(5) -0.003(5) C11 0.023(6) 0.029(6) 0.015(6) -0.004(5) 0.006(5) 0.000(5) C12 0.016(5) 0.017(5) 0.011(5) 0.000(4) -0.003(4) 0.001(4) C13 0.029(6) 0.020(6) 0.030(7) 0.006(5) 0.017(5) -0.001(5) C14 0.039(7) 0.013(5) 0.044(8) -0.006(5) 0.031(6) -0.003(5) C15 0.026(6) 0.034(7) 0.020(6) -0.015(5) 0.015(5) -0.006(5) C16 0.017(5) 0.032(7) 0.025(6) -0.004(5) 0.007(5) -0.001(5) C18 0.006(5) 0.030(6) 0.014(5) -0.002(4) 0.001(4) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O3 2.287(7) . ? Gd1 O1 2.337(7) . ? Gd1 O2 2.364(8) . ? Gd1 O5 2.384(7) . ? Gd1 O4 2.450(7) . ? Gd1 N5 2.481(9) . ? Gd1 N10 2.526(9) . ? Gd1 N12 2.539(9) . ? O1 N1 1.326(11) . ? O2 N6 1.340(12) . ? O3 N11 1.333(12) . ? N1 C5 1.345(14) . ? N1 C1 1.358(14) . ? N2 N3 1.343(13) . ? N2 C6 1.346(13) . ? N3 N4 1.315(13) . ? N4 N5 1.331(13) . ? N5 C6 1.339(13) . ? N6 C7 1.333(15) . ? N6 C11 1.357(15) . ? N7 C12 1.332(14) . ? N7 N8 1.343(13) . ? N8 N9 1.322(13) . ? N9 N10 1.361(12) . ? N10 C12 1.361(13) . ? N11 C17 1.343(14) . ? N11 C13 1.344(15) . ? N12 N13 1.347(13) . ? N12 C18 1.349(13) . ? N13 N14 1.322(13) . ? N14 N15 1.350(14) . ? N15 C18 1.336(14) . ? C1 C2 1.362(16) . ? C1 H1 0.9500 . ? C2 C3 1.384(17) . ? C2 H2 0.9500 . ? C3 C4 1.371(16) . ? C3 H3 0.9500 . ? C4 C5 1.400(15) . ? C4 H4 0.9500 . ? C5 C6 1.446(14) . ? C7 C8 1.387(18) . ? C7 H7 0.9500 . ? C8 C9 1.362(18) . ? C8 H8 0.9500 . ? C9 C10 1.386(17) . ? C9 H9 0.9500 . ? C17 C16 1.390(16) . ? C17 C18 1.440(16) . ? C10 C11 1.375(16) . ? C10 H10 0.9500 . ? C11 C12 1.458(16) . ? C13 C14 1.376(18) . ? C13 H13 0.9500 . ? C14 C15 1.371(18) . ? C14 H14 0.9500 . ? C15 C16 1.362(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 O3 Gd1 O1 145.2(3) . . ? O3 Gd1 O2 104.3(3) . . ? O1 Gd1 O2 83.5(3) . . ? O3 Gd1 O5 142.2(3) . . ? O1 Gd1 O5 72.0(3) . . ? O2 Gd1 O5 81.2(3) . . ? O3 Gd1 O4 78.6(3) . . ? O1 Gd1 O4 112.5(3) . . ? O2 Gd1 O4 148.2(2) . . ? O5 Gd1 O4 78.3(3) . . ? O3 Gd1 N5 83.3(3) . . ? O1 Gd1 N5 69.3(3) . . ? O2 Gd1 N5 137.3(3) . . ? O5 Gd1 N5 118.1(3) . . ? O4 Gd1 N5 74.3(3) . . ? O3 Gd1 N10 75.9(3) . . ? O1 Gd1 N10 76.1(3) . . ? O2 Gd1 N10 67.9(3) . . ? O5 Gd1 N10 137.6(3) . . ? O4 Gd1 N10 140.9(3) . . ? N5 Gd1 N10 73.8(3) . . ? O3 Gd1 N12 70.0(3) . . ? O1 Gd1 N12 143.1(3) . . ? O2 Gd1 N12 73.5(3) . . ? O5 Gd1 N12 76.2(3) . . ? O4 Gd1 N12 78.1(3) . . ? N5 Gd1 N12 144.9(3) . . ? N10 Gd1 N12 118.9(3) . . ? N1 O1 Gd1 132.1(6) . . ? N6 O2 Gd1 127.8(6) . . ? N11 O3 Gd1 130.5(6) . . ? O1 N1 C5 121.7(9) . . ? O1 N1 C1 116.6(9) . . ? C5 N1 C1 121.7(9) . . ? N3 N2 C6 104.1(8) . . ? N4 N3 N2 110.2(9) . . ? N3 N4 N5 109.1(9) . . ? N4 N5 C6 105.5(9) . . ? N4 N5 Gd1 126.2(7) . . ? C6 N5 Gd1 128.3(7) . . ? C7 N6 O2 117.7(9) . . ? C7 N6 C11 121.7(10) . . ? O2 N6 C11 120.6(9) . . ? C12 N7 N8 105.8(9) . . ? N9 N8 N7 109.6(9) . . ? N8 N9 N10 109.1(8) . . ? C12 N10 N9 104.4(8) . . ? C12 N10 Gd1 127.8(7) . . ? N9 N10 Gd1 127.8(7) . . ? O3 N11 C17 120.1(9) . . ? O3 N11 C13 117.8(10) . . ? C17 N11 C13 122.1(11) . . ? N13 N12 C18 105.5(9) . . ? N13 N12 Gd1 127.4(6) . . ? C18 N12 Gd1 125.4(7) . . ? N14 N13 N12 108.9(9) . . ? N13 N14 N15 109.5(9) . . ? C18 N15 N14 105.3(9) . . ? N1 C1 C2 120.7(11) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 119.4(11) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.2(11) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.6(11) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N1 C5 C4 118.2(10) . . ? N1 C5 C6 122.0(9) . . ? C4 C5 C6 119.8(10) . . ? N5 C6 N2 111.1(9) . . ? N5 C6 C5 126.4(9) . . ? N2 C6 C5 122.4(9) . . ? N6 C7 C8 120.7(12) . . ? N6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.1(12) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 119.4(12) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? N11 C17 C16 117.4(11) . . ? N11 C17 C18 121.1(10) . . ? C16 C17 C18 121.5(10) . . ? C11 C10 C9 120.5(11) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? N6 C11 C10 118.6(11) . . ? N6 C11 C12 120.3(10) . . ? C10 C11 C12 121.0(11) . . ? N7 C12 N10 111.1(9) . . ? N7 C12 C11 122.8(10) . . ? N10 C12 C11 125.6(9) . . ? N11 C13 C14 121.0(12) . . ? N11 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 118.1(11) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C16 C15 C14 120.0(11) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.2(12) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? N15 C18 N12 110.7(10) . . ? N15 C18 C17 122.5(9) . . ? N12 C18 C17 126.4(10) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.662 _refine_diff_density_min -5.483 _refine_diff_density_rms 0.207 data_s09n1m_Gd-1 _database_code_depnum_ccdc_archive 'CCDC 232483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 Gd N15 O6.50' _chemical_formula_weight 712.78 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' Gd Gd -0.1653 3.9035 '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' _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 9.0273(9) _cell_length_b 17.714(3) _cell_length_c 16.7480(19) _cell_angle_alpha 90.00 _cell_angle_beta 99.819(9) _cell_angle_gamma 90.00 _cell_volume 2639.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description columnar _exptl_crystal_colour colorless _exptl_crystal_size_max 0.204 _exptl_crystal_size_mid 0.108 _exptl_crystal_size_min 0.064 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 2.581 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6567 _exptl_absorpt_correction_T_max 0.8539 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24502 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.95 _reflns_number_total 6489 _reflns_number_gt 5496 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.8672P] 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 6489 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0712 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd 0.577064(13) 0.206064(7) 0.182144(7) 0.01252(5) Uani 1 1 d . . . O1 O 0.7622(2) 0.13238(13) 0.12767(13) 0.0220(4) Uani 1 1 d . . . H01A H 0.745(4) 0.1042(19) 0.082(2) 0.026 Uiso 1 1 d . . . H01B H 0.831(4) 0.129(2) 0.147(2) 0.026 Uiso 1 1 d . . . O2 O 0.8014(2) 0.27220(12) 0.24290(13) 0.0183(4) Uani 1 1 d . . . H02A H 0.817(4) 0.2854(17) 0.291(2) 0.022 Uiso 1 1 d . . . H02B H 0.866(4) 0.264(2) 0.226(2) 0.022 Uiso 1 1 d . . . O3 O 0.5054(2) 0.33437(11) 0.19378(12) 0.0194(4) Uani 1 1 d . . . H03A H 0.464(4) 0.352(2) 0.166(2) 0.023 Uiso 1 1 d . . . H03B H 0.572(3) 0.380(2) 0.1849(17) 0.023 Uiso 1 1 d . . . O4 O 0.6073(3) 0.44056(13) 0.30712(15) 0.0284(5) Uani 1 1 d . . . H04A H 0.681(4) 0.428(2) 0.345(2) 0.034 Uiso 1 1 d . . . H04B H 0.637(4) 0.471(2) 0.285(2) 0.034 Uiso 1 1 d . . . O5 O 0.8872(3) 0.06152(12) 0.58879(13) 0.0252(5) Uani 1 1 d . . . H05A H 0.956(4) 0.034(2) 0.591(2) 0.030 Uiso 1 1 d . . . H05B H 0.870(4) 0.071(2) 0.544(2) 0.030 Uiso 1 1 d . . . O6 O 0.7225(3) 0.04413(15) 0.99035(16) 0.0497(7) Uani 1 1 d . . . O7 O 1.0134(6) 0.0076(4) 0.0564(3) 0.0569(15) Uani 0.50 1 d P . . N1 N 0.6505(3) 0.29036(12) 0.06192(14) 0.0178(5) Uani 1 1 d . . . N2 N 0.4013(3) 0.18670(14) -0.09407(15) 0.0233(5) Uani 1 1 d . . . N3 N 0.3277(3) 0.12590(15) -0.07224(15) 0.0260(5) Uani 1 1 d . . . N4 N 0.3626(3) 0.11520(14) 0.00628(15) 0.0249(5) Uani 1 1 d . . . N5 N 0.4599(3) 0.16923(13) 0.03820(14) 0.0190(5) Uani 1 1 d . . . N6 N 0.4409(2) 0.07530(13) 0.18926(14) 0.0176(5) Uani 1 1 d . . . N7 N 0.0812(2) 0.16193(14) 0.20485(15) 0.0201(5) Uani 1 1 d . . . N8 N 0.0681(2) 0.23737(15) 0.19451(14) 0.0202(5) Uani 1 1 d . . . N9 N 0.1945(3) 0.26703(14) 0.18041(14) 0.0196(5) Uani 1 1 d . . . N10 N 0.2957(3) 0.21058(12) 0.18123(15) 0.0166(5) Uani 1 1 d . . . N11 N 0.5303(3) 0.22908(13) 0.33235(13) 0.0172(5) Uani 1 1 d . . . N12 N 0.7222(2) 0.12153(13) 0.29386(13) 0.0177(5) Uani 1 1 d . . . N13 N 0.8190(3) 0.06324(13) 0.29541(14) 0.0209(5) Uani 1 1 d . . . N14 N 0.8614(3) 0.04146(14) 0.37094(15) 0.0240(5) Uani 1 1 d . . . N15 N 0.7950(3) 0.08455(14) 0.42071(15) 0.0236(5) Uani 1 1 d . . . C1 C 0.7423(3) 0.34975(17) 0.07415(18) 0.0236(6) Uani 1 1 d . . . H1 H 0.7873 0.3616 0.1282 0.028 Uiso 1 1 calc R . . C2 C 0.7757(4) 0.39526(17) 0.0119(2) 0.0291(7) Uani 1 1 d . . . H2 H 0.8419 0.4370 0.0234 0.035 Uiso 1 1 calc R . . C3 C 0.7110(4) 0.37873(18) -0.06689(19) 0.0292(7) Uani 1 1 d . . . H3 H 0.7334 0.4083 -0.1106 0.035 Uiso 1 1 calc R . . C4 C 0.6129(4) 0.31816(18) -0.08106(18) 0.0258(6) Uani 1 1 d . . . H4 H 0.5656 0.3058 -0.1346 0.031 Uiso 1 1 calc R . . C5 C 0.5853(3) 0.27587(16) -0.01537(17) 0.0186(5) Uani 1 1 d . . . C6 C 0.4820(3) 0.21150(14) -0.02482(17) 0.0172(5) Uani 1 1 d . . . C7 C 0.5128(3) 0.00888(16) 0.19447(18) 0.0229(6) Uani 1 1 d . . . H7 H 0.6087 0.0068 0.1784 0.027 Uiso 1 1 calc R . . C8 C 0.4555(4) -0.05686(17) 0.2219(2) 0.0293(7) Uani 1 1 d . . . H8 H 0.5113 -0.1025 0.2246 0.035 Uiso 1 1 calc R . . C9 C 0.3150(4) -0.05517(17) 0.2455(2) 0.0302(7) Uani 1 1 d . . . H9 H 0.2753 -0.0986 0.2675 0.036 Uiso 1 1 calc R . . C10 C 0.2347(3) 0.01190(17) 0.23586(19) 0.0260(6) Uani 1 1 d . . . H10 H 0.1362 0.0146 0.2486 0.031 Uiso 1 1 calc R . . C11 C 0.3003(3) 0.07519(16) 0.20733(17) 0.0193(6) Uani 1 1 d . . . C12 C 0.2232(3) 0.14801(15) 0.19706(16) 0.0173(5) Uani 1 1 d . . . C13 C 0.4368(3) 0.28315(16) 0.35100(18) 0.0207(6) Uani 1 1 d . . . H13 H 0.3755 0.3092 0.3080 0.025 Uiso 1 1 calc R . . C14 C 0.4260(4) 0.30243(18) 0.4300(2) 0.0300(7) Uani 1 1 d . . . H14 H 0.3602 0.3416 0.4407 0.036 Uiso 1 1 calc R . . C15 C 0.5104(4) 0.2647(2) 0.49180(19) 0.0326(7) Uani 1 1 d . . . H15 H 0.5039 0.2772 0.5462 0.039 Uiso 1 1 calc R . . C16 C 0.6063(4) 0.20782(16) 0.47592(18) 0.0255(7) Uani 1 1 d . . . H16 H 0.6655 0.1804 0.5186 0.031 Uiso 1 1 calc R . . C17 C 0.6131(3) 0.19219(15) 0.39506(17) 0.0178(5) Uani 1 1 d . . . C18 C 0.7103(3) 0.13287(15) 0.37139(16) 0.0172(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.01231(7) 0.01346(8) 0.01168(7) 0.00062(4) 0.00172(5) 0.00007(4) O1 0.0175(10) 0.0298(12) 0.0182(11) -0.0031(9) 0.0018(8) 0.0048(9) O2 0.0141(9) 0.0253(11) 0.0154(10) -0.0039(8) 0.0021(8) -0.0005(8) O3 0.0231(11) 0.0154(10) 0.0194(11) 0.0040(8) 0.0025(8) 0.0015(8) O4 0.0249(11) 0.0255(12) 0.0314(13) 0.0097(10) -0.0052(9) -0.0055(9) O5 0.0324(12) 0.0218(11) 0.0189(10) -0.0021(9) -0.0025(9) 0.0064(9) O6 0.076(2) 0.0368(14) 0.0427(16) 0.0007(12) 0.0275(14) -0.0004(13) O7 0.056(4) 0.067(4) 0.049(3) 0.005(3) 0.013(3) 0.011(3) N1 0.0213(12) 0.0160(12) 0.0167(11) -0.0005(9) 0.0048(9) 0.0005(9) N2 0.0264(13) 0.0256(13) 0.0166(12) -0.0019(10) 0.0000(10) 0.0007(10) N3 0.0286(13) 0.0286(14) 0.0188(12) -0.0028(10) -0.0022(10) -0.0034(11) N4 0.0275(13) 0.0255(13) 0.0195(12) -0.0001(10) -0.0026(10) -0.0058(11) N5 0.0209(12) 0.0193(12) 0.0162(11) 0.0009(9) 0.0011(9) -0.0025(9) N6 0.0194(11) 0.0154(11) 0.0176(11) -0.0001(9) 0.0021(9) 0.0002(9) N7 0.0170(11) 0.0227(13) 0.0215(12) -0.0009(10) 0.0057(9) -0.0008(9) N8 0.0170(12) 0.0238(13) 0.0195(12) -0.0022(10) 0.0029(9) 0.0026(9) N9 0.0165(11) 0.0209(12) 0.0210(12) -0.0032(10) 0.0021(9) 0.0026(9) N10 0.0141(11) 0.0152(11) 0.0204(12) -0.0015(9) 0.0027(9) 0.0013(8) N11 0.0179(11) 0.0201(11) 0.0141(11) 0.0001(9) 0.0041(9) 0.0007(9) N12 0.0193(11) 0.0172(11) 0.0164(11) -0.0003(9) 0.0021(9) 0.0033(9) N13 0.0235(12) 0.0182(12) 0.0199(12) 0.0014(9) 0.0005(9) 0.0046(9) N14 0.0270(13) 0.0218(13) 0.0216(13) 0.0015(10) -0.0004(10) 0.0053(10) N15 0.0281(13) 0.0222(13) 0.0192(12) 0.0026(10) 0.0003(10) 0.0057(10) C1 0.0253(15) 0.0228(15) 0.0229(14) 0.0018(12) 0.0044(12) -0.0027(12) C2 0.0323(17) 0.0233(16) 0.0338(17) 0.0044(13) 0.0116(14) -0.0039(13) C3 0.0365(17) 0.0279(16) 0.0257(16) 0.0085(13) 0.0128(13) 0.0027(14) C4 0.0345(17) 0.0265(15) 0.0173(14) 0.0039(12) 0.0073(12) 0.0029(13) C5 0.0207(14) 0.0193(13) 0.0161(13) 0.0015(10) 0.0038(11) 0.0042(11) C6 0.0186(13) 0.0188(14) 0.0140(13) 0.0014(10) 0.0020(10) 0.0042(10) C7 0.0192(14) 0.0193(14) 0.0304(16) -0.0014(12) 0.0049(12) 0.0006(11) C8 0.0357(17) 0.0154(14) 0.0348(18) -0.0003(12) 0.0004(14) 0.0034(12) C9 0.0381(18) 0.0181(15) 0.0342(18) 0.0026(13) 0.0055(14) -0.0073(13) C10 0.0251(15) 0.0233(15) 0.0307(17) 0.0003(12) 0.0076(12) -0.0063(12) C11 0.0200(13) 0.0197(14) 0.0185(13) -0.0017(11) 0.0039(10) -0.0025(11) C12 0.0186(13) 0.0167(13) 0.0175(13) -0.0013(10) 0.0054(10) -0.0018(10) C13 0.0181(14) 0.0250(15) 0.0189(14) 0.0033(11) 0.0024(11) 0.0036(11) C14 0.0296(17) 0.0355(18) 0.0243(16) -0.0071(13) 0.0031(13) 0.0056(13) C15 0.0440(19) 0.0402(19) 0.0147(14) -0.0060(13) 0.0081(13) 0.0077(16) C16 0.0334(17) 0.0271(16) 0.0154(14) 0.0021(11) 0.0028(12) 0.0050(12) C17 0.0179(13) 0.0197(14) 0.0156(13) 0.0010(10) 0.0024(10) -0.0012(10) C18 0.0187(13) 0.0182(13) 0.0136(12) 0.0023(10) 0.0001(10) -0.0010(10) _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 O3 2.380(2) . ? Gd1 O2 2.409(2) . ? Gd1 O1 2.418(2) . ? Gd1 N10 2.538(2) . ? Gd1 N5 2.547(2) . ? Gd1 N12 2.573(2) . ? Gd1 N6 2.635(2) . ? Gd1 N11 2.652(2) . ? Gd1 N1 2.679(2) . ? N1 C1 1.333(4) . ? N1 C5 1.352(4) . ? N2 C6 1.334(4) . ? N2 N3 1.348(3) . ? N3 N4 1.313(3) . ? N4 N5 1.347(3) . ? N5 C6 1.336(3) . ? N6 C7 1.340(4) . ? N6 C11 1.354(3) . ? N7 C12 1.333(3) . ? N7 N8 1.350(4) . ? N8 N9 1.314(3) . ? N9 N10 1.353(3) . ? N10 C12 1.337(3) . ? N11 C13 1.348(4) . ? N11 C17 1.349(4) . ? N12 C18 1.336(3) . ? N12 N13 1.350(3) . ? N13 N14 1.315(3) . ? N14 N15 1.345(3) . ? N15 C18 1.336(3) . ? C1 C2 1.391(4) . ? C2 C3 1.380(5) . ? C3 C4 1.386(4) . ? C4 C5 1.388(4) . ? C5 C6 1.465(4) . ? C7 C8 1.384(4) . ? C8 C9 1.392(5) . ? C9 C10 1.387(4) . ? C10 C11 1.390(4) . ? C11 C12 1.462(4) . ? C13 C14 1.387(4) . ? C14 C15 1.352(5) . ? C15 C16 1.383(4) . ? C16 C17 1.394(4) . ? C17 C18 1.466(4) . ? 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 O3 Gd1 O2 73.85(7) . . ? O3 Gd1 O1 139.57(7) . . ? O2 Gd1 O1 80.60(7) . . ? O3 Gd1 N10 71.62(7) . . ? O2 Gd1 N10 139.04(7) . . ? O1 Gd1 N10 140.33(7) . . ? O3 Gd1 N5 104.32(7) . . ? O2 Gd1 N5 135.05(7) . . ? O1 Gd1 N5 72.95(7) . . ? N10 Gd1 N5 75.45(8) . . ? O3 Gd1 N12 127.44(7) . . ? O2 Gd1 N12 71.88(7) . . ? O1 Gd1 N12 70.21(7) . . ? N10 Gd1 N12 114.04(7) . . ? N5 Gd1 N12 128.08(7) . . ? O3 Gd1 N6 134.45(7) . . ? O2 Gd1 N6 140.66(7) . . ? O1 Gd1 N6 84.29(7) . . ? N10 Gd1 N6 63.50(7) . . ? N5 Gd1 N6 72.30(7) . . ? N12 Gd1 N6 68.85(7) . . ? O3 Gd1 N11 71.71(7) . . ? O2 Gd1 N11 77.46(7) . . ? O1 Gd1 N11 132.27(7) . . ? N10 Gd1 N11 71.35(7) . . ? N5 Gd1 N11 146.07(7) . . ? N12 Gd1 N11 62.83(7) . . ? N6 Gd1 N11 86.64(7) . . ? O3 Gd1 N1 68.59(7) . . ? O2 Gd1 N1 75.44(7) . . ? O1 Gd1 N1 75.04(7) . . ? N10 Gd1 N1 110.69(7) . . ? N5 Gd1 N1 63.09(7) . . ? N12 Gd1 N1 135.25(7) . . ? N6 Gd1 N1 134.52(7) . . ? N11 Gd1 N1 136.62(7) . . ? C1 N1 C5 117.0(2) . . ? C1 N1 Gd1 123.45(19) . . ? C5 N1 Gd1 119.39(18) . . ? C6 N2 N3 104.4(2) . . ? N4 N3 N2 110.0(2) . . ? N3 N4 N5 108.9(2) . . ? C6 N5 N4 105.0(2) . . ? C6 N5 Gd1 120.69(18) . . ? N4 N5 Gd1 134.05(17) . . ? C7 N6 C11 116.5(2) . . ? C7 N6 Gd1 123.39(18) . . ? C11 N6 Gd1 118.28(17) . . ? C12 N7 N8 103.6(2) . . ? N9 N8 N7 111.0(2) . . ? N8 N9 N10 108.0(2) . . ? C12 N10 N9 105.2(2) . . ? C12 N10 Gd1 119.75(17) . . ? N9 N10 Gd1 134.15(17) . . ? C13 N11 C17 116.7(2) . . ? C13 N11 Gd1 122.42(18) . . ? C17 N11 Gd1 120.48(18) . . ? C18 N12 N13 104.8(2) . . ? C18 N12 Gd1 120.25(17) . . ? N13 N12 Gd1 134.96(17) . . ? N14 N13 N12 108.9(2) . . ? N13 N14 N15 110.0(2) . . ? C18 N15 N14 104.4(2) . . ? N1 C1 C2 123.4(3) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 C4 118.8(3) . . ? C3 C4 C5 118.5(3) . . ? N1 C5 C4 123.3(3) . . ? N1 C5 C6 114.6(2) . . ? C4 C5 C6 122.1(3) . . ? N2 C6 N5 111.7(2) . . ? N2 C6 C5 126.4(3) . . ? N5 C6 C5 121.9(2) . . ? N6 C7 C8 123.8(3) . . ? C7 C8 C9 119.1(3) . . ? C10 C9 C8 118.0(3) . . ? C9 C10 C11 119.1(3) . . ? N6 C11 C10 123.3(3) . . ? N6 C11 C12 114.7(2) . . ? C10 C11 C12 122.0(3) . . ? N7 C12 N10 112.2(2) . . ? N7 C12 C11 126.7(2) . . ? N10 C12 C11 121.0(2) . . ? N11 C13 C14 123.0(3) . . ? C15 C14 C13 119.1(3) . . ? C14 C15 C16 120.2(3) . . ? C15 C16 C17 117.7(3) . . ? N11 C17 C16 123.4(3) . . ? N11 C17 C18 114.5(2) . . ? C16 C17 C18 122.2(3) . . ? N15 C18 N12 111.9(2) . . ? N15 C18 C17 126.7(2) . . ? N12 C18 C17 121.4(2) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.95 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 2.368 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.121