# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_aa _database_code_depnum_ccdc_archive 'CCDC 861481' #TrackingRef 'aa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 Eu N6 O7' _chemical_formula_weight 553.28 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.537(3) _cell_length_b 14.403(2) _cell_length_c 7.9836(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.630(12) _cell_angle_gamma 90.00 _cell_volume 1888.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5150 _cell_measurement_theta_min 2.4797 _cell_measurement_theta_max 27.4719 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 3.375 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5375 _exptl_absorpt_correction_T_max 0.6681 _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12536 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3507 _reflns_number_gt 3258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 2.1c(K.Brandenburg, 1999)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _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^)+(0.0359P)^2^+2.8395P] 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 3507 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.448813(9) 0.615929(11) 0.052477(19) 0.02473(5) Uani 1 1 d . . . O4 O 0.36539(14) 0.49055(17) 0.1056(3) 0.0416(7) Uani 1 1 d . . . O5 O 0.42521(15) 0.35653(18) 0.0496(3) 0.0424(7) Uani 1 1 d . . . O6 O 0.34446(13) 0.67821(16) 0.2042(3) 0.0352(6) Uani 1 1 d . . . O7 O 0.37602(13) 0.81585(17) 0.3182(3) 0.0343(6) Uani 1 1 d . . . O3 O 0.45710(14) 0.50941(17) -0.1746(3) 0.0364(7) Uani 1 1 d . . . O2 O 0.47576(16) 0.39198(16) -0.3373(3) 0.0359(7) Uani 1 1 d . . . O1 O 0.48590(15) 0.77664(16) 0.0931(3) 0.0405(7) Uani 1 1 d . . . H1W H 0.5165 0.8023 0.0407 0.061 Uiso 1 1 d R . . H2W H 0.4627 0.7902 0.1853 0.061 Uiso 1 1 d R . . C4 C 0.3010(2) 0.3508(2) 0.1695(4) 0.0307(9) Uani 1 1 d . . . C5 C 0.3014(2) 0.2554(2) 0.1725(4) 0.0345(9) Uani 1 1 d . . . H5 H 0.3430 0.2216 0.1324 0.041 Uiso 1 1 calc R . . C6 C 0.2365(2) 0.2112(3) 0.2384(4) 0.0354(10) Uani 1 1 d . . . C7 C 0.1752(2) 0.2634(3) 0.2993(4) 0.0349(10) Uani 1 1 d . . . C8 C 0.1733(2) 0.3607(3) 0.2954(5) 0.0422(10) Uani 1 1 d . . . H8 H 0.1317 0.3946 0.3352 0.051 Uiso 1 1 calc R . . C9 C 0.2368(2) 0.4022(3) 0.2293(4) 0.0346(9) Uani 1 1 d . . . H9 H 0.2381 0.4666 0.2231 0.042 Uiso 1 1 calc R . . C3 C 0.3681(2) 0.4035(2) 0.1029(5) 0.0331(9) Uani 1 1 d . . . C11 C 0.2415(2) 0.7616(2) 0.3239(4) 0.0303(9) Uani 1 1 d . . . C12 C 0.1936(2) 0.6824(3) 0.3438(5) 0.0424(10) Uani 1 1 d . . . H12 H 0.2143 0.6240 0.3235 0.051 Uiso 1 1 calc R . . C13 C 0.1175(2) 0.6896(3) 0.3922(5) 0.0459(11) Uani 1 1 d . . . H13 H 0.0866 0.6370 0.4081 0.055 Uiso 1 1 calc R . . C14 C 0.0877(2) 0.7782(3) 0.4171(5) 0.0406(10) Uani 1 1 d . . . C15 C 0.1344(2) 0.8554(3) 0.3929(5) 0.0365(10) Uani 1 1 d . . . C16 C 0.2130(2) 0.8495(3) 0.3492(4) 0.0338(9) Uani 1 1 d . . . H16 H 0.2446 0.9020 0.3376 0.041 Uiso 1 1 calc R . . C10 C 0.3266(2) 0.7497(2) 0.2795(4) 0.0294(8) Uani 1 1 d . . . C2 C 0.4385(2) 0.4666(2) -0.3111(4) 0.0296(9) Uani 1 1 d . . . C1 C 0.3729(2) 0.5011(3) -0.4385(5) 0.0450(11) Uani 1 1 d . . . H1A H 0.3795 0.4747 -0.5465 0.067 Uiso 1 1 calc R . . H1B H 0.3758 0.5675 -0.4451 0.067 Uiso 1 1 calc R . . H1C H 0.3209 0.4833 -0.4063 0.067 Uiso 1 1 calc R . . N1 N 0.2210(2) 0.1184(2) 0.2568(4) 0.0442(10) Uani 1 1 d . . . N2 N 0.1532(2) 0.1116(2) 0.3287(5) 0.0478(10) Uani 1 1 d . . . N3 N 0.12446(18) 0.1977(2) 0.3530(4) 0.0467(9) Uani 1 1 d . . . H3 H 0.0803 0.2095 0.3962 0.056 Uiso 1 1 calc R . . N4 N 0.0149(2) 0.8084(3) 0.4670(5) 0.0528(10) Uani 1 1 d . . . N5 N 0.0158(2) 0.8984(2) 0.4720(5) 0.0570(11) Uani 1 1 d . . . N6 N 0.08630(19) 0.9290(2) 0.4281(4) 0.0492(10) Uani 1 1 d . . . H6 H 0.0998 0.9865 0.4225 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.02645(10) 0.01942(11) 0.02952(9) -0.00018(6) 0.00842(8) 0.00031(5) O4 0.0436(13) 0.0198(13) 0.0656(15) -0.0031(11) 0.0237(12) -0.0047(10) O5 0.0376(12) 0.0275(14) 0.0666(16) -0.0031(12) 0.0260(11) -0.0031(12) O6 0.0348(12) 0.0264(13) 0.0476(12) -0.0070(10) 0.0177(10) -0.0007(10) O7 0.0298(11) 0.0304(13) 0.0435(12) -0.0091(10) 0.0076(10) -0.0065(10) O3 0.0450(13) 0.0342(14) 0.0293(11) -0.0068(10) 0.0012(10) 0.0114(11) O2 0.0451(15) 0.0348(15) 0.0277(11) -0.0104(9) 0.0033(11) 0.0024(10) O1 0.0582(14) 0.0239(13) 0.0446(12) -0.0052(10) 0.0281(11) -0.0077(11) C4 0.0313(16) 0.0208(17) 0.0415(17) -0.0022(15) 0.0097(14) -0.0065(14) C5 0.0367(17) 0.0269(19) 0.0432(17) 0.0015(15) 0.0185(15) 0.0001(14) C6 0.0340(18) 0.035(2) 0.0365(17) 0.0049(15) 0.0012(15) -0.0058(15) C7 0.0304(17) 0.036(2) 0.0390(18) 0.0020(15) 0.0068(15) -0.0063(14) C8 0.0351(18) 0.038(2) 0.056(2) 0.0021(18) 0.0159(17) 0.0050(16) C9 0.0366(18) 0.0235(18) 0.0453(19) 0.0034(15) 0.0116(16) 0.0026(14) C3 0.0287(17) 0.0256(18) 0.0454(19) -0.0065(15) 0.0066(16) 0.0008(14) C11 0.0321(17) 0.0314(19) 0.0282(15) -0.0048(14) 0.0071(14) -0.0023(14) C12 0.045(2) 0.030(2) 0.054(2) -0.0091(17) 0.0166(17) -0.0016(16) C13 0.045(2) 0.028(2) 0.068(2) -0.0024(18) 0.0225(18) -0.0034(16) C14 0.0353(18) 0.039(2) 0.0512(19) 0.0010(17) 0.0208(16) 0.0020(15) C15 0.0370(18) 0.0287(19) 0.0449(19) 0.0021(16) 0.0090(16) 0.0013(16) C16 0.0330(17) 0.0319(19) 0.0385(17) 0.0001(15) 0.0124(15) 0.0005(15) C10 0.0318(16) 0.0282(18) 0.0285(15) 0.0031(14) 0.0053(14) -0.0026(14) C2 0.0417(18) 0.0250(18) 0.0234(14) 0.0051(13) 0.0097(14) -0.0046(14) C1 0.046(2) 0.043(2) 0.044(2) 0.0057(18) -0.0031(18) 0.0032(18) N1 0.0493(19) 0.0341(19) 0.0530(18) 0.0052(13) 0.0215(16) -0.0102(13) N2 0.0489(19) 0.033(2) 0.066(2) 0.0046(14) 0.0257(17) -0.0028(13) N3 0.0372(15) 0.044(2) 0.0632(19) 0.0047(16) 0.0238(14) -0.0056(14) N4 0.0411(17) 0.048(2) 0.074(2) -0.0011(18) 0.0256(16) -0.0007(15) N5 0.0389(18) 0.045(2) 0.092(3) 0.0050(19) 0.0287(18) 0.0039(15) N6 0.0427(16) 0.0299(19) 0.080(2) 0.0020(16) 0.0292(16) 0.0050(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O7 2.322(2) 4_575 ? Eu1 O4 2.341(2) . ? Eu1 O5 2.357(3) 3_665 ? Eu1 O3 2.391(2) . ? Eu1 O6 2.394(2) . ? Eu1 O1 2.407(2) . ? Eu1 O2 2.467(2) 3_665 ? Eu1 O3 2.506(2) 3_665 ? Eu1 C2 2.874(3) 3_665 ? Eu1 Eu1 3.8791(5) 3_665 ? Eu1 H2W 2.7238 . ? O4 C3 1.255(4) . ? O5 C3 1.274(4) . ? O5 Eu1 2.357(3) 3_665 ? O6 C10 1.245(4) . ? O7 C10 1.270(4) . ? O7 Eu1 2.322(2) 4_576 ? O3 C2 1.258(4) . ? O3 Eu1 2.506(2) 3_665 ? O2 C2 1.269(4) . ? O2 Eu1 2.467(2) 3_665 ? O1 H2W 0.8901 . ? O1 H1W 0.7849 . ? O1 H2W 0.8901 . ? C4 C5 1.374(5) . ? C4 C9 1.421(5) . ? C4 C3 1.493(5) . ? C5 C6 1.401(5) . ? C5 H5 0.9300 . ? C6 N1 1.372(5) . ? C6 C7 1.394(5) . ? C7 N3 1.366(5) . ? C7 C8 1.401(5) . ? C8 C9 1.366(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C11 C16 1.373(5) . ? C11 C12 1.409(5) . ? C11 C10 1.500(5) . ? C12 C13 1.362(5) . ? C12 H12 0.9300 . ? C13 C14 1.391(5) . ? C13 H13 0.9300 . ? C14 N4 1.381(5) . ? C14 C15 1.381(5) . ? C15 N6 1.374(5) . ? C15 C16 1.386(5) . ? C16 H16 0.9300 . ? C2 C1 1.484(5) . ? C2 Eu1 2.874(3) 3_665 ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N1 N2 1.321(5) . ? N2 N3 1.349(4) . ? N3 H3 0.8600 . ? N4 N5 1.298(5) . ? N5 N6 1.331(5) . ? N6 H6 0.8600 . ? 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 O7 Eu1 O4 102.17(8) 4_575 . ? O7 Eu1 O5 92.69(8) 4_575 3_665 ? O4 Eu1 O5 139.07(9) . 3_665 ? O7 Eu1 O3 74.37(8) 4_575 . ? O4 Eu1 O3 74.28(9) . . ? O5 Eu1 O3 73.46(9) 3_665 . ? O7 Eu1 O6 84.95(8) 4_575 . ? O4 Eu1 O6 73.92(8) . . ? O5 Eu1 O6 146.05(8) 3_665 . ? O3 Eu1 O6 137.04(8) . . ? O7 Eu1 O1 78.58(8) 4_575 . ? O4 Eu1 O1 149.74(8) . . ? O5 Eu1 O1 70.31(9) 3_665 . ? O3 Eu1 O1 133.10(8) . . ? O6 Eu1 O1 76.04(8) . . ? O7 Eu1 O2 157.21(8) 4_575 3_665 ? O4 Eu1 O2 92.47(8) . 3_665 ? O5 Eu1 O2 87.34(9) 3_665 3_665 ? O3 Eu1 O2 127.03(8) . 3_665 ? O6 Eu1 O2 82.43(8) . 3_665 ? O1 Eu1 O2 79.99(8) . 3_665 ? O7 Eu1 O3 149.21(8) 4_575 3_665 ? O4 Eu1 O3 74.11(8) . 3_665 ? O5 Eu1 O3 73.85(8) 3_665 3_665 ? O3 Eu1 O3 75.26(8) . 3_665 ? O6 Eu1 O3 121.63(8) . 3_665 ? O1 Eu1 O3 120.21(8) . 3_665 ? O2 Eu1 O3 51.89(7) 3_665 3_665 ? O7 Eu1 C2 170.55(9) 4_575 3_665 ? O4 Eu1 C2 84.10(9) . 3_665 ? O5 Eu1 C2 78.02(9) 3_665 3_665 ? O3 Eu1 C2 100.95(9) . 3_665 ? O6 Eu1 C2 103.71(8) . 3_665 ? O1 Eu1 C2 99.62(9) . 3_665 ? O2 Eu1 C2 26.08(8) 3_665 3_665 ? O3 Eu1 C2 25.91(8) 3_665 3_665 ? O7 Eu1 Eu1 112.88(6) 4_575 3_665 ? O4 Eu1 Eu1 69.89(6) . 3_665 ? O5 Eu1 Eu1 69.20(6) 3_665 3_665 ? O3 Eu1 Eu1 38.67(5) . 3_665 ? O6 Eu1 Eu1 142.17(6) . 3_665 ? O1 Eu1 Eu1 138.27(6) . 3_665 ? O2 Eu1 Eu1 88.43(6) 3_665 3_665 ? O3 Eu1 Eu1 36.59(5) 3_665 3_665 ? C2 Eu1 Eu1 62.36(6) 3_665 3_665 ? O7 Eu1 H2W 86.3 4_575 . ? O4 Eu1 H2W 131.7 . . ? O5 Eu1 H2W 86.7 3_665 . ? O3 Eu1 H2W 151.3 . . ? O6 Eu1 H2W 59.4 . . ? O1 Eu1 H2W 18.7 . . ? O2 Eu1 H2W 70.9 3_665 . ? O3 Eu1 H2W 119.5 3_665 . ? C2 Eu1 H2W 94.8 3_665 . ? Eu1 Eu1 H2W 149.1 3_665 . ? C3 O4 Eu1 138.1(2) . . ? C3 O5 Eu1 138.2(2) . 3_665 ? C10 O6 Eu1 141.2(2) . . ? C10 O7 Eu1 140.6(2) . 4_576 ? C2 O3 Eu1 160.2(2) . . ? C2 O3 Eu1 93.6(2) . 3_665 ? Eu1 O3 Eu1 104.74(8) . 3_665 ? C2 O2 Eu1 95.18(18) . 3_665 ? H2W O1 Eu1 101.2 . . ? H2W O1 H1W 134.7 . . ? Eu1 O1 H1W 123.4 . . ? H2W O1 H2W 0.0 . . ? Eu1 O1 H2W 101.2 . . ? H1W O1 H2W 134.7 . . ? C5 C4 C9 121.2(3) . . ? C5 C4 C3 120.8(3) . . ? C9 C4 C3 118.0(3) . . ? C4 C5 C6 117.3(3) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? N1 C6 C7 109.6(3) . . ? N1 C6 C5 130.0(3) . . ? C7 C6 C5 120.4(3) . . ? N3 C7 C6 103.5(3) . . ? N3 C7 C8 133.4(3) . . ? C6 C7 C8 123.1(3) . . ? C9 C8 C7 115.5(3) . . ? C9 C8 H8 122.3 . . ? C7 C8 H8 122.3 . . ? C8 C9 C4 122.6(3) . . ? C8 C9 H9 118.7 . . ? C4 C9 H9 118.7 . . ? O4 C3 O5 124.5(3) . . ? O4 C3 C4 118.2(3) . . ? O5 C3 C4 117.3(3) . . ? C16 C11 C12 121.5(3) . . ? C16 C11 C10 119.2(3) . . ? C12 C11 C10 119.3(3) . . ? C13 C12 C11 121.4(4) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 117.7(4) . . ? C12 C13 H13 121.2 . . ? C14 C13 H13 121.2 . . ? N4 C14 C15 107.9(3) . . ? N4 C14 C13 131.7(4) . . ? C15 C14 C13 120.4(3) . . ? N6 C15 C14 104.2(3) . . ? N6 C15 C16 132.9(4) . . ? C14 C15 C16 122.8(4) . . ? C11 C16 C15 116.2(3) . . ? C11 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? O6 C10 O7 123.8(3) . . ? O6 C10 C11 119.3(3) . . ? O7 C10 C11 116.8(3) . . ? O3 C2 O2 118.9(3) . . ? O3 C2 C1 121.1(3) . . ? O2 C2 C1 120.0(3) . . ? O3 C2 Eu1 60.49(16) . 3_665 ? O2 C2 Eu1 58.74(16) . 3_665 ? C1 C2 Eu1 173.0(2) . 3_665 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 N1 C6 107.3(3) . . ? N1 N2 N3 109.0(3) . . ? N2 N3 C7 110.6(3) . . ? N2 N3 H3 124.7 . . ? C7 N3 H3 124.7 . . ? N5 N4 C14 108.4(3) . . ? N4 N5 N6 109.2(3) . . ? N5 N6 C15 110.2(3) . . ? N5 N6 H6 124.9 . . ? C15 N6 H6 124.9 . . ? 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 O7 Eu1 O4 C3 114.2(3) 4_575 . . . ? O5 Eu1 O4 C3 5.4(4) 3_665 . . . ? O3 Eu1 O4 C3 44.5(3) . . . . ? O6 Eu1 O4 C3 -164.7(4) . . . . ? O1 Eu1 O4 C3 -157.6(3) . . . . ? O2 Eu1 O4 C3 -83.3(4) 3_665 . . . ? O3 Eu1 O4 C3 -34.2(3) 3_665 . . . ? C2 Eu1 O4 C3 -58.6(4) 3_665 . . . ? Eu1 Eu1 O4 C3 4.1(3) 3_665 . . . ? O7 Eu1 O6 C10 -87.9(3) 4_575 . . . ? O4 Eu1 O6 C10 167.9(3) . . . . ? O5 Eu1 O6 C10 -0.6(4) 3_665 . . . ? O3 Eu1 O6 C10 -148.5(3) . . . . ? O1 Eu1 O6 C10 -8.4(3) . . . . ? O2 Eu1 O6 C10 73.1(3) 3_665 . . . ? O3 Eu1 O6 C10 108.7(3) 3_665 . . . ? C2 Eu1 O6 C10 88.3(3) 3_665 . . . ? Eu1 Eu1 O6 C10 150.6(3) 3_665 . . . ? O7 Eu1 O3 C2 -27.7(7) 4_575 . . . ? O4 Eu1 O3 C2 80.1(7) . . . . ? O5 Eu1 O3 C2 -125.4(7) 3_665 . . . ? O6 Eu1 O3 C2 36.6(7) . . . . ? O1 Eu1 O3 C2 -84.8(7) . . . . ? O2 Eu1 O3 C2 161.1(6) 3_665 . . . ? O3 Eu1 O3 C2 157.4(7) 3_665 . . . ? C2 Eu1 O3 C2 160.7(6) 3_665 . . . ? Eu1 Eu1 O3 C2 157.4(7) 3_665 . . . ? O7 Eu1 O3 Eu1 174.88(11) 4_575 . . 3_665 ? O4 Eu1 O3 Eu1 -77.29(10) . . . 3_665 ? O5 Eu1 O3 Eu1 77.18(10) 3_665 . . 3_665 ? O6 Eu1 O3 Eu1 -120.87(10) . . . 3_665 ? O1 Eu1 O3 Eu1 117.80(11) . . . 3_665 ? O2 Eu1 O3 Eu1 3.72(14) 3_665 . . 3_665 ? O3 Eu1 O3 Eu1 0.0 3_665 . . 3_665 ? C2 Eu1 O3 Eu1 3.32(11) 3_665 . . 3_665 ? O7 Eu1 O1 H2W 113.2 4_575 . . . ? O4 Eu1 O1 H2W 18.5 . . . . ? O5 Eu1 O1 H2W -149.8 3_665 . . . ? O3 Eu1 O1 H2W 168.7 . . . . ? O6 Eu1 O1 H2W 25.6 . . . . ? O2 Eu1 O1 H2W -59.0 3_665 . . . ? O3 Eu1 O1 H2W -93.1 3_665 . . . ? C2 Eu1 O1 H2W -76.3 3_665 . . . ? Eu1 Eu1 O1 H2W -135.1 3_665 . . . ? C9 C4 C5 C6 -0.7(5) . . . . ? C3 C4 C5 C6 179.5(3) . . . . ? C4 C5 C6 N1 179.9(3) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? N1 C6 C7 N3 0.0(4) . . . . ? C5 C6 C7 N3 -179.5(3) . . . . ? N1 C6 C7 C8 -179.0(3) . . . . ? C5 C6 C7 C8 1.5(5) . . . . ? N3 C7 C8 C9 -179.6(4) . . . . ? C6 C7 C8 C9 -0.9(5) . . . . ? C7 C8 C9 C4 -0.5(5) . . . . ? C5 C4 C9 C8 1.3(5) . . . . ? C3 C4 C9 C8 -178.8(3) . . . . ? Eu1 O4 C3 O5 -6.1(6) . . . . ? Eu1 O4 C3 C4 172.5(2) . . . . ? Eu1 O5 C3 O4 3.8(6) 3_665 . . . ? Eu1 O5 C3 C4 -174.9(2) 3_665 . . . ? C5 C4 C3 O4 -178.9(3) . . . . ? C9 C4 C3 O4 1.3(5) . . . . ? C5 C4 C3 O5 -0.1(5) . . . . ? C9 C4 C3 O5 -180.0(3) . . . . ? C16 C11 C12 C13 -1.3(5) . . . . ? C10 C11 C12 C13 176.7(3) . . . . ? C11 C12 C13 C14 1.7(6) . . . . ? C12 C13 C14 N4 -179.2(4) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? N4 C14 C15 N6 -0.7(4) . . . . ? C13 C14 C15 N6 179.9(3) . . . . ? N4 C14 C15 C16 177.1(3) . . . . ? C13 C14 C15 C16 -2.3(6) . . . . ? C12 C11 C16 C15 -0.8(5) . . . . ? C10 C11 C16 C15 -178.9(3) . . . . ? N6 C15 C16 C11 179.7(4) . . . . ? C14 C15 C16 C11 2.6(5) . . . . ? Eu1 O6 C10 O7 -11.7(5) . . . . ? Eu1 O6 C10 C11 166.4(2) . . . . ? Eu1 O7 C10 O6 -109.8(4) 4_576 . . . ? Eu1 O7 C10 C11 72.0(4) 4_576 . . . ? C16 C11 C10 O6 -156.7(3) . . . . ? C12 C11 C10 O6 25.3(4) . . . . ? C16 C11 C10 O7 21.5(4) . . . . ? C12 C11 C10 O7 -156.5(3) . . . . ? Eu1 O3 C2 O2 -164.6(5) . . . . ? Eu1 O3 C2 O2 -6.5(3) 3_665 . . . ? Eu1 O3 C2 C1 13.9(9) . . . . ? Eu1 O3 C2 C1 172.1(3) 3_665 . . . ? Eu1 O3 C2 Eu1 -158.2(7) . . . 3_665 ? Eu1 O2 C2 O3 6.6(3) 3_665 . . . ? Eu1 O2 C2 C1 -172.0(3) 3_665 . . . ? C7 C6 N1 N2 -0.8(4) . . . . ? C5 C6 N1 N2 178.6(4) . . . . ? C6 N1 N2 N3 1.3(4) . . . . ? N1 N2 N3 C7 -1.3(4) . . . . ? C6 C7 N3 N2 0.8(4) . . . . ? C8 C7 N3 N2 179.7(4) . . . . ? C15 C14 N4 N5 0.6(5) . . . . ? C13 C14 N4 N5 179.9(4) . . . . ? C14 N4 N5 N6 -0.2(5) . . . . ? N4 N5 N6 C15 -0.2(5) . . . . ? C14 C15 N6 N5 0.6(4) . . . . ? C16 C15 N6 N5 -176.9(4) . . . . ? 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 N3 H3 N5 0.86 2.54 3.161(5) 130.3 3_566 N3 H3 N4 0.86 2.03 2.855(5) 159.5 3_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.336 _refine_diff_density_min -1.831 _refine_diff_density_rms 0.152 data_lizh _database_code_depnum_ccdc_archive 'CCDC 866558' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N6 O7 Sm' _chemical_formula_weight 551.67 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.5570(9) _cell_length_b 14.4501(7) _cell_length_c 8.0012(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.648(4) _cell_angle_gamma 90.00 _cell_volume 1901.42(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4370 _cell_measurement_theta_min 2.4768 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 3.142 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5015 _exptl_absorpt_correction_T_max 1.0000 _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12565 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3526 _reflns_number_gt 3353 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 2.1c(K.Brandenburg, 1999)' _computing_publication_material 'Diamond Version 2.1c(K.Brandenburg, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0381P)^2^+4.1141P] 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 3526 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.051580(17) 0.616026(19) 0.44747(4) 0.02459(14) Uani 1 1 d . . . O1 O 0.0135(3) 0.7774(3) 0.4053(6) 0.0411(11) Uani 1 1 d . . . H1W H 0.0117 0.8064 0.5128 0.062 Uiso 1 1 d R . . H2W H 0.0531 0.8080 0.3463 0.062 Uiso 1 1 d R . . O2 O -0.0244(3) 0.6072(3) 0.1606(6) 0.0369(11) Uani 1 1 d . . . O3 O -0.0432(3) 0.4908(3) 0.3244(5) 0.0361(10) Uani 1 1 d . . . O4 O 0.1349(3) 0.4901(3) 0.3945(6) 0.0423(11) Uani 1 1 d . . . O5 O 0.0749(3) 0.3568(3) 0.4505(6) 0.0429(12) Uani 1 1 d . . . O6 O 0.1249(2) 0.6840(3) 0.6830(5) 0.0361(10) Uani 1 1 d . . . O7 O 0.1564(2) 0.8219(3) 0.7960(6) 0.0362(10) Uani 1 1 d . . . N1 N 0.2789(4) 0.1180(3) 0.2428(9) 0.0434(15) Uani 1 1 d . . . N2 N 0.3463(4) 0.1116(4) 0.1715(9) 0.0463(16) Uani 1 1 d . . . N3 N 0.3745(3) 0.1976(4) 0.1462(8) 0.0421(14) Uani 1 1 d . . . H3 H 0.4183 0.2095 0.1019 0.051 Uiso 1 1 calc R . . N4 N 0.4141(4) 0.5713(4) 0.5717(9) 0.0481(15) Uani 1 1 d . . . N5 N 0.4845(4) 0.6011(5) 0.5282(10) 0.0567(19) Uani 1 1 d . . . N6 N 0.4857(4) 0.6920(4) 0.5344(9) 0.0523(16) Uani 1 1 d . . . C1 C -0.1273(4) 0.4982(5) 0.0611(8) 0.0432(16) Uani 1 1 d . . . H1B H -0.1790 0.5217 0.0853 0.065 Uiso 1 1 d R . . H1C H -0.1278 0.4318 0.0662 0.065 Uiso 1 1 d R . . H1A H -0.1174 0.5176 -0.0495 0.065 Uiso 1 1 d R . . C2 C -0.0618(3) 0.5339(4) 0.1868(7) 0.0278(12) Uani 1 1 d . . . C3 C 0.1317(4) 0.4022(4) 0.3972(9) 0.0345(14) Uani 1 1 d . . . C4 C 0.1997(4) 0.3514(4) 0.3303(8) 0.0311(13) Uani 1 1 d . . . C5 C 0.1988(4) 0.2551(4) 0.3273(8) 0.0350(14) Uani 1 1 d . . . H5 H 0.1569 0.2217 0.3669 0.042 Uiso 1 1 calc R . . C6 C 0.2637(4) 0.2106(4) 0.2621(8) 0.0337(14) Uani 1 1 d . . . C7 C 0.3244(4) 0.2628(4) 0.2003(8) 0.0352(14) Uani 1 1 d . . . C8 C 0.3262(4) 0.3597(5) 0.2037(9) 0.0396(16) Uani 1 1 d . . . H8 H 0.3675 0.3937 0.1632 0.047 Uiso 1 1 calc R . . C9 C 0.2629(3) 0.4009(4) 0.2708(8) 0.0322(14) Uani 1 1 d . . . H9 H 0.2620 0.4651 0.2772 0.039 Uiso 1 1 calc R . . C10 C 0.1744(3) 0.7497(4) 0.7218(7) 0.0290(13) Uani 1 1 d . . . C11 C 0.2597(3) 0.7378(4) 0.6773(7) 0.0288(13) Uani 1 1 d . . . C12 C 0.2876(4) 0.6505(4) 0.6519(8) 0.0334(14) Uani 1 1 d . . . H12 H 0.2560 0.5984 0.6642 0.040 Uiso 1 1 calc R . . C13 C 0.3657(4) 0.6442(5) 0.6070(9) 0.0363(14) Uani 1 1 d . . . C14 C 0.4133(4) 0.7211(5) 0.5829(9) 0.0379(15) Uani 1 1 d . . . C15 C 0.3840(4) 0.8095(5) 0.6094(10) 0.0480(18) Uani 1 1 d . . . H15 H 0.4151 0.8618 0.5944 0.058 Uiso 1 1 calc R . . C16 C 0.3079(4) 0.8167(5) 0.6583(9) 0.0431(16) Uani 1 1 d . . . H16 H 0.2875 0.8750 0.6795 0.052 Uiso 1 1 calc R . . H1 H 0.407(4) 0.505(5) 0.575(8) 0.05(2) Uiso 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 Sm1 0.0276(2) 0.0176(2) 0.0301(2) -0.00002(10) 0.00970(15) -0.00056(10) O1 0.064(3) 0.018(2) 0.046(3) 0.0013(19) 0.029(2) 0.002(2) O2 0.052(3) 0.027(2) 0.032(2) 0.0106(17) 0.003(2) -0.0051(19) O3 0.044(2) 0.031(2) 0.031(2) 0.0043(18) -0.0022(19) -0.0114(19) O4 0.042(2) 0.023(2) 0.066(3) 0.004(2) 0.023(2) 0.0078(19) O5 0.039(2) 0.026(2) 0.069(3) 0.003(2) 0.027(2) 0.002(2) O6 0.032(2) 0.029(2) 0.048(3) -0.0093(19) 0.008(2) -0.0060(18) O7 0.034(2) 0.025(2) 0.053(3) -0.0068(19) 0.019(2) 0.0007(18) N1 0.045(3) 0.030(3) 0.060(4) -0.005(2) 0.022(3) 0.010(2) N2 0.043(3) 0.034(3) 0.066(4) -0.005(3) 0.020(3) 0.006(2) N3 0.037(3) 0.037(3) 0.056(4) -0.002(3) 0.022(3) 0.002(2) N4 0.041(3) 0.030(3) 0.078(5) -0.002(3) 0.026(3) 0.001(3) N5 0.040(3) 0.047(4) 0.090(5) 0.001(3) 0.035(4) 0.001(3) N6 0.040(3) 0.043(4) 0.078(5) 0.001(3) 0.024(3) -0.001(3) C1 0.049(4) 0.038(4) 0.040(4) -0.001(3) -0.003(3) 0.002(3) C2 0.035(3) 0.025(3) 0.024(3) 0.002(2) 0.010(2) 0.007(2) C3 0.035(3) 0.026(3) 0.043(4) 0.007(3) 0.008(3) 0.003(3) C4 0.032(3) 0.025(3) 0.036(3) -0.001(3) 0.006(3) 0.008(3) C5 0.033(3) 0.030(3) 0.045(4) 0.003(3) 0.018(3) -0.003(3) C6 0.034(3) 0.031(3) 0.037(3) -0.001(3) 0.007(3) 0.005(3) C7 0.031(3) 0.035(4) 0.041(4) -0.003(3) 0.011(3) 0.008(3) C8 0.029(3) 0.034(3) 0.058(4) 0.003(3) 0.015(3) -0.006(3) C9 0.027(3) 0.024(3) 0.048(4) 0.003(3) 0.014(3) 0.000(2) C10 0.030(3) 0.030(3) 0.028(3) -0.001(2) 0.010(2) 0.001(2) C11 0.027(3) 0.028(3) 0.034(3) -0.005(2) 0.014(3) -0.002(2) C12 0.033(3) 0.027(3) 0.044(4) -0.002(3) 0.017(3) 0.001(3) C13 0.033(3) 0.028(3) 0.050(4) -0.002(3) 0.014(3) 0.001(3) C14 0.033(3) 0.037(4) 0.048(4) -0.001(3) 0.023(3) 0.001(3) C15 0.048(4) 0.027(3) 0.073(5) -0.002(3) 0.024(4) -0.006(3) C16 0.044(4) 0.028(3) 0.059(5) -0.005(3) 0.012(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O6 2.336(4) . ? Sm1 O4 2.352(4) . ? Sm1 O5 2.366(4) 3_566 ? Sm1 O7 2.403(4) 4_575 ? Sm1 O3 2.407(4) 3_566 ? Sm1 O1 2.428(4) . ? Sm1 O2 2.489(4) . ? Sm1 O3 2.520(4) . ? Sm1 Sm1 3.8988(6) 3_566 ? O1 H1W 0.9600 . ? O1 H2W 0.9600 . ? O2 C2 1.257(7) . ? O3 C2 1.272(7) . ? O3 Sm1 2.407(4) 3_566 ? O4 C3 1.271(7) . ? O5 C3 1.262(8) . ? O5 Sm1 2.366(4) 3_566 ? O6 C10 1.270(7) . ? O7 C10 1.254(7) . ? O7 Sm1 2.403(4) 4_576 ? N1 N2 1.313(8) . ? N1 C6 1.374(8) . ? N2 N3 1.351(7) . ? N3 C7 1.358(8) . ? N3 H3 0.8600 . ? N4 N5 1.326(9) . ? N4 C13 1.371(9) . ? N4 H1 0.97(7) . ? N5 N6 1.314(8) . ? N6 C14 1.368(9) . ? C1 C2 1.484(8) . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1A 0.9600 . ? C3 C4 1.494(8) . ? C4 C5 1.391(9) . ? C4 C9 1.396(8) . ? C5 C6 1.404(8) . ? C5 H5 0.9300 . ? C6 C7 1.393(9) . ? C7 C8 1.402(9) . ? C8 C9 1.368(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.505(7) . ? C11 C12 1.367(8) . ? C11 C16 1.411(9) . ? C12 C13 1.384(8) . ? C12 H12 0.9300 . ? C13 C14 1.389(9) . ? C14 C15 1.392(9) . ? C15 C16 1.365(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 O6 Sm1 O4 102.11(16) . . ? O6 Sm1 O5 92.84(16) . 3_566 ? O4 Sm1 O5 138.74(15) . 3_566 ? O6 Sm1 O7 84.94(15) . 4_575 ? O4 Sm1 O7 74.01(14) . 4_575 ? O5 Sm1 O7 146.28(15) 3_566 4_575 ? O6 Sm1 O3 74.20(14) . 3_566 ? O4 Sm1 O3 74.17(15) . 3_566 ? O5 Sm1 O3 73.37(15) 3_566 3_566 ? O7 Sm1 O3 136.92(14) 4_575 3_566 ? O6 Sm1 O1 79.10(16) . . ? O4 Sm1 O1 150.02(15) . . ? O5 Sm1 O1 70.28(16) 3_566 . ? O7 Sm1 O1 76.29(14) 4_575 . ? O3 Sm1 O1 133.16(15) 3_566 . ? O6 Sm1 O2 157.65(14) . . ? O4 Sm1 O2 92.22(16) . . ? O5 Sm1 O2 87.35(17) 3_566 . ? O7 Sm1 O2 82.61(15) 4_575 . ? O3 Sm1 O2 126.82(13) 3_566 . ? O1 Sm1 O2 79.95(15) . . ? O6 Sm1 O3 149.19(14) . . ? O4 Sm1 O3 74.08(15) . . ? O5 Sm1 O3 73.63(15) 3_566 . ? O7 Sm1 O3 121.64(15) 4_575 . ? O3 Sm1 O3 75.40(15) 3_566 . ? O1 Sm1 O3 119.68(15) . . ? O2 Sm1 O3 51.52(13) . . ? O6 Sm1 Sm1 112.77(11) . 3_566 ? O4 Sm1 Sm1 69.77(10) . 3_566 ? O5 Sm1 Sm1 68.97(11) 3_566 3_566 ? O7 Sm1 Sm1 142.17(10) 4_575 3_566 ? O3 Sm1 Sm1 38.72(9) 3_566 3_566 ? O1 Sm1 Sm1 137.93(11) . 3_566 ? O2 Sm1 Sm1 88.15(9) . 3_566 ? O3 Sm1 Sm1 36.68(9) . 3_566 ? Sm1 O1 H1W 109.2 . . ? Sm1 O1 H2W 109.2 . . ? H1W O1 H2W 109.5 . . ? C2 O2 Sm1 95.5(3) . . ? C2 O3 Sm1 160.3(4) . 3_566 ? C2 O3 Sm1 93.6(3) . . ? Sm1 O3 Sm1 104.60(15) 3_566 . ? C3 O4 Sm1 138.0(4) . . ? C3 O5 Sm1 139.0(4) . 3_566 ? C10 O6 Sm1 140.5(4) . . ? C10 O7 Sm1 140.8(4) . 4_576 ? N2 N1 C6 107.0(5) . . ? N1 N2 N3 109.1(5) . . ? N2 N3 C7 110.8(5) . . ? N2 N3 H3 124.6 . . ? C7 N3 H3 124.6 . . ? N5 N4 C13 110.9(6) . . ? N5 N4 H1 116(4) . . ? C13 N4 H1 133(4) . . ? N6 N5 N4 108.9(6) . . ? N5 N6 C14 107.9(6) . . ? C2 C1 H1B 109.8 . . ? C2 C1 H1C 109.2 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? O2 C2 O3 118.9(5) . . ? O2 C2 C1 121.1(5) . . ? O3 C2 C1 120.0(5) . . ? O5 C3 O4 124.1(6) . . ? O5 C3 C4 119.2(6) . . ? O4 C3 C4 116.7(6) . . ? C5 C4 C9 120.9(6) . . ? C5 C4 C3 119.4(6) . . ? C9 C4 C3 119.8(5) . . ? C4 C5 C6 117.2(6) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? N1 C6 C7 109.8(5) . . ? N1 C6 C5 130.3(6) . . ? C7 C6 C5 119.9(6) . . ? N3 C7 C6 103.3(6) . . ? N3 C7 C8 133.4(6) . . ? C6 C7 C8 123.3(6) . . ? C9 C8 C7 115.3(6) . . ? C9 C8 H8 122.4 . . ? C7 C8 H8 122.4 . . ? C8 C9 C4 123.4(6) . . ? C8 C9 H9 118.3 . . ? C4 C9 H9 118.3 . . ? O7 C10 O6 123.8(5) . . ? O7 C10 C11 119.2(5) . . ? O6 C10 C11 117.0(5) . . ? C12 C11 C16 121.6(5) . . ? C12 C11 C10 118.9(5) . . ? C16 C11 C10 119.5(5) . . ? C11 C12 C13 116.3(6) . . ? C11 C12 H12 121.9 . . ? C13 C12 H12 121.9 . . ? N4 C13 C12 133.6(6) . . ? N4 C13 C14 103.4(6) . . ? C12 C13 C14 123.0(6) . . ? N6 C14 C13 108.9(6) . . ? N6 C14 C15 131.1(6) . . ? C13 C14 C15 120.0(6) . . ? C16 C15 C14 117.6(6) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? C15 C16 C11 121.5(6) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? 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 N4 H1 N5 0.97(7) 2.57(7) 3.159(9) 120(5) 3_666 N4 H1 N2 0.97(7) 2.15(7) 3.016(8) 148(6) 4_566 N3 H3 N5 0.86 2.55 3.178(8) 130.3 2_645 N3 H3 N6 0.86 2.04 2.868(9) 159.9 2_645 O1 H2W O6 0.96 1.87 2.764(6) 154.0 4_575 O1 H1W O2 0.96 1.86 2.765(6) 154.9 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.329 _refine_diff_density_min -2.192 _refine_diff_density_rms 0.154 data_lylizh _database_code_depnum_ccdc_archive 'CCDC 866559' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N6 O7 Tb' _chemical_formula_weight 560.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.5521(8) _cell_length_b 14.3705(6) _cell_length_c 7.9630(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.360(4) _cell_angle_gamma 90.00 _cell_volume 1882.44(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4564 _cell_measurement_theta_min 2.4761 _cell_measurement_theta_max 27.4758 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 3.811 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4290 _exptl_absorpt_correction_T_max 1.0000 _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12447 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3500 _reflns_number_gt 3271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 2.1c(K.Brandenburg, 1999)' _computing_publication_material 'Diamond Version 2.1c(K.Brandenburg, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0385P)^2^+4.7505P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3500 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Tb1 Tb 0.449508(14) 0.115845(16) 0.05242(3) 0.02278(11) Uani 1 1 d . . . O1 O 0.4880(2) 0.2748(2) 0.0952(5) 0.0378(9) Uani 1 1 d . . . H1W H 0.4977 0.3018 -0.0110 0.057 Uiso 1 1 d R . . H2W H 0.4448 0.3079 0.1403 0.057 Uiso 1 1 d R . . O2 O 0.5234(3) 0.1087(2) 0.3354(5) 0.0342(9) Uani 1 1 d . . . O3 O 0.5425(2) -0.0088(2) 0.1725(4) 0.0333(9) Uani 1 1 d . . . O4 O 0.5741(2) 0.1428(3) -0.0517(5) 0.0407(10) Uani 1 1 d . . . O5 O 0.6336(2) 0.0080(3) -0.1072(5) 0.0386(10) Uani 1 1 d . . . O6 O 0.3465(2) 0.1785(2) 0.2038(5) 0.0321(8) Uani 1 1 d . . . O7 O 0.3782(2) 0.3161(3) 0.3215(5) 0.0325(8) Uani 1 1 d . . . N1 N 0.7789(4) 0.3817(3) -0.2586(7) 0.0435(14) Uani 1 1 d . . . N2 N 0.8474(4) 0.3877(3) -0.3273(8) 0.0478(15) Uani 1 1 d . . . N3 N 0.8755(3) 0.3014(4) -0.3530(7) 0.0448(13) Uani 1 1 d . . . H3 H 0.9193 0.2893 -0.3978 0.054 Uiso 1 1 calc R . . N4 N 0.0871(3) 0.4288(4) 0.4300(7) 0.0496(14) Uani 1 1 d . . . H4 H 0.1001 0.4865 0.4246 0.060 Uiso 1 1 calc R . . N5 N 0.0165(4) 0.3977(4) 0.4737(9) 0.0567(17) Uani 1 1 d . . . N6 N 0.0160(3) 0.3072(4) 0.4672(8) 0.0530(15) Uani 1 1 d . . . C1 C 0.6269(4) -0.0011(4) 0.4372(7) 0.0414(14) Uani 1 1 d . . . H1A H 0.6789 0.0178 0.4062 0.062 Uiso 1 1 calc R . . H2A H 0.6245 -0.0678 0.4414 0.062 Uiso 1 1 calc R . . H3A H 0.6196 0.0240 0.5462 0.062 Uiso 1 1 calc R . . C2 C 0.5610(3) 0.0344(4) 0.3089(6) 0.0293(12) Uani 1 1 d . . . C3 C 0.6300(3) 0.0946(4) -0.1043(7) 0.0303(12) Uani 1 1 d . . . C4 C 0.6990(3) 0.1492(4) -0.1699(6) 0.0285(11) Uani 1 1 d . . . C5 C 0.7626(3) 0.0969(4) -0.2298(7) 0.0331(13) Uani 1 1 d . . . H5 H 0.7608 0.0323 -0.2247 0.040 Uiso 1 1 calc R . . C6 C 0.8265(4) 0.1390(4) -0.2950(8) 0.0397(14) Uani 1 1 d . . . H6 H 0.8682 0.1050 -0.3347 0.048 Uiso 1 1 calc R . . C7 C 0.8250(3) 0.2358(4) -0.2983(7) 0.0319(12) Uani 1 1 d . . . C8 C 0.7630(3) 0.2884(4) -0.2397(7) 0.0337(12) Uani 1 1 d . . . C9 C 0.6978(3) 0.2438(4) -0.1739(7) 0.0328(12) Uani 1 1 d . . . H9 H 0.6557 0.2775 -0.1349 0.039 Uiso 1 1 calc R . . C10 C 0.3287(3) 0.2507(4) 0.2801(6) 0.0268(11) Uani 1 1 d . . . C11 C 0.2432(3) 0.2621(4) 0.3256(6) 0.0287(11) Uani 1 1 d . . . C12 C 0.1958(4) 0.1821(4) 0.3460(8) 0.0412(14) Uani 1 1 d . . . H12 H 0.2173 0.1237 0.3272 0.049 Uiso 1 1 calc R . . C13 C 0.1189(4) 0.1885(4) 0.3927(9) 0.0454(15) Uani 1 1 d . . . H13 H 0.0878 0.1357 0.4059 0.054 Uiso 1 1 calc R . . C14 C 0.0890(3) 0.2777(4) 0.4199(8) 0.0379(14) Uani 1 1 d . . . C15 C 0.1361(3) 0.3561(4) 0.3949(7) 0.0353(13) Uani 1 1 d . . . C16 C 0.2147(3) 0.3499(4) 0.3509(7) 0.0332(12) Uani 1 1 d . . . H16 H 0.2463 0.4025 0.3392 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tb1 0.02345(19) 0.01797(18) 0.02860(17) -0.00003(8) 0.01040(13) 0.00020(8) O1 0.049(3) 0.023(2) 0.046(2) -0.0018(16) 0.0230(19) -0.0063(17) O2 0.039(3) 0.033(2) 0.031(2) -0.0116(15) 0.0047(18) 0.0031(16) O3 0.045(2) 0.025(2) 0.0304(18) -0.0047(15) 0.0038(17) 0.0074(16) O4 0.034(2) 0.028(2) 0.065(3) -0.0038(19) 0.028(2) -0.0046(19) O5 0.036(2) 0.020(2) 0.064(3) -0.0036(17) 0.026(2) -0.0067(16) O6 0.032(2) 0.022(2) 0.045(2) -0.0089(16) 0.0176(17) -0.0009(15) O7 0.0236(19) 0.034(2) 0.042(2) -0.0097(16) 0.0112(16) -0.0051(15) N1 0.045(4) 0.032(3) 0.057(3) 0.004(2) 0.020(3) -0.008(2) N2 0.045(4) 0.035(3) 0.068(4) 0.005(2) 0.025(3) -0.008(2) N3 0.034(3) 0.043(3) 0.061(3) 0.000(3) 0.023(3) -0.006(2) N4 0.037(3) 0.032(3) 0.086(4) 0.003(3) 0.032(3) 0.001(2) N5 0.036(3) 0.049(4) 0.091(5) -0.001(3) 0.033(3) 0.005(2) N6 0.036(3) 0.046(4) 0.082(4) -0.002(3) 0.030(3) -0.001(3) C1 0.040(4) 0.041(4) 0.042(3) 0.003(3) 0.000(3) -0.001(3) C2 0.037(3) 0.030(3) 0.023(2) 0.001(2) 0.012(2) -0.007(2) C3 0.026(3) 0.022(3) 0.045(3) -0.001(2) 0.016(2) 0.000(2) C4 0.023(3) 0.027(3) 0.037(3) 0.002(2) 0.012(2) -0.007(2) C5 0.031(3) 0.023(3) 0.048(3) -0.002(2) 0.017(3) -0.001(2) C6 0.028(3) 0.037(3) 0.057(4) -0.004(3) 0.016(3) 0.007(3) C7 0.028(3) 0.030(3) 0.040(3) 0.004(2) 0.013(2) -0.008(2) C8 0.031(3) 0.033(3) 0.039(3) 0.001(2) 0.013(2) -0.005(2) C9 0.031(3) 0.026(3) 0.044(3) 0.002(2) 0.017(2) -0.002(2) C10 0.025(3) 0.030(3) 0.028(2) -0.001(2) 0.010(2) -0.002(2) C11 0.021(3) 0.032(3) 0.036(3) -0.002(2) 0.012(2) 0.000(2) C12 0.040(4) 0.026(3) 0.061(4) -0.009(3) 0.019(3) 0.002(2) C13 0.035(3) 0.031(3) 0.074(4) -0.004(3) 0.023(3) -0.011(3) C14 0.030(3) 0.036(3) 0.052(3) -0.003(3) 0.021(3) -0.004(2) C15 0.031(3) 0.028(3) 0.048(3) 0.000(3) 0.013(3) 0.003(2) C16 0.028(3) 0.027(3) 0.047(3) -0.001(2) 0.017(3) 0.000(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 Tb1 O7 2.291(4) 4_565 ? Tb1 O5 2.320(3) 3_655 ? Tb1 O4 2.338(4) . ? Tb1 O6 2.372(3) . ? Tb1 O3 2.376(3) 3_655 ? Tb1 O1 2.386(4) . ? Tb1 O2 2.444(4) . ? Tb1 O3 2.483(4) . ? Tb1 Tb1 3.8582(5) 3_655 ? O1 H1W 0.9600 . ? O1 H2W 0.9600 . ? O2 C2 1.265(6) . ? O3 C2 1.259(6) . ? O3 Tb1 2.376(3) 3_655 ? O4 C3 1.264(6) . ? O5 C3 1.247(6) . ? O5 Tb1 2.320(3) 3_655 ? O6 C10 1.253(6) . ? O7 C10 1.266(6) . ? O7 Tb1 2.291(4) 4_566 ? N1 N2 1.315(7) . ? N1 C8 1.378(7) . ? N2 N3 1.349(7) . ? N3 C7 1.364(7) . ? N3 H3 0.8600 . ? N4 N5 1.334(8) . ? N4 C15 1.370(8) . ? N4 H4 0.8600 . ? N5 N6 1.302(7) . ? N6 C14 1.372(8) . ? C1 C2 1.499(8) . ? C1 H1A 0.9600 . ? C1 H2A 0.9600 . ? C1 H3A 0.9600 . ? C3 C4 1.524(7) . ? C4 C9 1.360(8) . ? C4 C5 1.418(7) . ? C5 C6 1.370(8) . ? C5 H5 0.9300 . ? C6 C7 1.392(8) . ? C6 H6 0.9300 . ? C7 C8 1.395(7) . ? C8 C9 1.405(7) . ? C9 H9 0.9300 . ? C10 C11 1.509(7) . ? C11 C16 1.370(7) . ? C11 C12 1.411(8) . ? C12 C13 1.368(8) . ? C12 H12 0.9300 . ? C13 C14 1.399(8) . ? C13 H13 0.9300 . ? C14 C15 1.398(8) . ? C15 C16 1.387(7) . ? C16 H16 0.9300 . ? 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 O7 Tb1 O5 102.39(14) 4_565 3_655 ? O7 Tb1 O4 92.35(14) 4_565 . ? O5 Tb1 O4 139.31(13) 3_655 . ? O7 Tb1 O6 84.86(13) 4_565 . ? O5 Tb1 O6 73.80(12) 3_655 . ? O4 Tb1 O6 146.01(13) . . ? O7 Tb1 O3 74.82(13) 4_565 3_655 ? O5 Tb1 O3 74.27(13) 3_655 3_655 ? O4 Tb1 O3 73.43(14) . 3_655 ? O6 Tb1 O3 137.07(13) . 3_655 ? O7 Tb1 O1 79.13(14) 4_565 . ? O5 Tb1 O1 149.53(13) 3_655 . ? O4 Tb1 O1 70.15(14) . . ? O6 Tb1 O1 76.07(12) . . ? O3 Tb1 O1 133.74(13) 3_655 . ? O7 Tb1 O2 156.70(13) 4_565 . ? O5 Tb1 O2 92.36(14) 3_655 . ? O4 Tb1 O2 87.89(14) . . ? O6 Tb1 O2 82.04(13) . . ? O3 Tb1 O2 127.16(12) 3_655 . ? O1 Tb1 O2 79.06(13) . . ? O7 Tb1 O3 149.23(12) 4_565 . ? O5 Tb1 O3 74.32(13) 3_655 . ? O4 Tb1 O3 73.89(14) . . ? O6 Tb1 O3 121.86(12) . . ? O3 Tb1 O3 74.90(13) 3_655 . ? O1 Tb1 O3 119.44(13) . . ? O2 Tb1 O3 52.35(12) . . ? O7 Tb1 Tb1 113.06(9) 4_565 3_655 ? O5 Tb1 Tb1 70.07(9) 3_655 3_655 ? O4 Tb1 Tb1 69.26(10) . 3_655 ? O6 Tb1 Tb1 142.25(9) . 3_655 ? O3 Tb1 Tb1 38.41(9) 3_655 3_655 ? O1 Tb1 Tb1 137.91(10) . 3_655 ? O2 Tb1 Tb1 88.79(8) . 3_655 ? O3 Tb1 Tb1 36.48(8) . 3_655 ? Tb1 O1 H1W 109.2 . . ? Tb1 O1 H2W 109.3 . . ? H1W O1 H2W 109.5 . . ? C2 O2 Tb1 95.0(3) . . ? C2 O3 Tb1 160.3(4) . 3_655 ? C2 O3 Tb1 93.3(3) . . ? Tb1 O3 Tb1 105.10(13) 3_655 . ? C3 O4 Tb1 137.2(4) . . ? C3 O5 Tb1 137.0(3) . 3_655 ? C10 O6 Tb1 141.3(3) . . ? C10 O7 Tb1 141.9(3) . 4_566 ? N2 N1 C8 107.1(5) . . ? N1 N2 N3 109.3(4) . . ? N2 N3 C7 110.6(5) . . ? N2 N3 H3 124.7 . . ? C7 N3 H3 124.7 . . ? N5 N4 C15 110.8(5) . . ? N5 N4 H4 124.6 . . ? C15 N4 H4 124.6 . . ? N6 N5 N4 109.0(5) . . ? N5 N6 C14 108.5(5) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H2A 109.5 . . ? H1A C1 H2A 109.5 . . ? C2 C1 H3A 109.5 . . ? H1A C1 H3A 109.5 . . ? H2A C1 H3A 109.5 . . ? O3 C2 O2 118.9(5) . . ? O3 C2 C1 120.6(5) . . ? O2 C2 C1 120.6(5) . . ? O5 C3 O4 126.2(5) . . ? O5 C3 C4 117.9(5) . . ? O4 C3 C4 115.8(5) . . ? C9 C4 C5 122.1(5) . . ? C9 C4 C3 120.9(5) . . ? C5 C4 C3 117.0(5) . . ? C6 C5 C4 121.8(5) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C7 115.8(5) . . ? C5 C6 H6 122.1 . . ? C7 C6 H6 122.1 . . ? N3 C7 C6 133.3(5) . . ? N3 C7 C8 103.5(5) . . ? C6 C7 C8 123.2(5) . . ? N1 C8 C7 109.5(5) . . ? N1 C8 C9 130.5(5) . . ? C7 C8 C9 120.1(5) . . ? C4 C9 C8 117.1(5) . . ? C4 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? O6 C10 O7 124.2(5) . . ? O6 C10 C11 118.9(5) . . ? O7 C10 C11 116.9(4) . . ? C16 C11 C12 122.0(5) . . ? C16 C11 C10 118.9(5) . . ? C12 C11 C10 119.2(5) . . ? C13 C12 C11 121.5(5) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 117.4(5) . . ? C12 C13 H13 121.3 . . ? C14 C13 H13 121.3 . . ? N6 C14 C15 108.2(5) . . ? N6 C14 C13 131.5(5) . . ? C15 C14 C13 120.2(5) . . ? N4 C15 C16 133.9(6) . . ? N4 C15 C14 103.5(5) . . ? C16 C15 C14 122.6(5) . . ? C11 C16 C15 116.3(5) . . ? C11 C16 H16 121.8 . . ? C15 C16 H16 121.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.912 _refine_diff_density_min -1.695 _refine_diff_density_rms 0.144 data_Er _database_code_depnum_ccdc_archive 'CCDC 873843' #TrackingRef 'Er.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 Er N6 O7' _chemical_formula_weight 568.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.512(3) _cell_length_b 14.256(2) _cell_length_c 7.9218(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.345(12) _cell_angle_gamma 90.00 _cell_volume 1853.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5062 _cell_measurement_theta_min 2.4820 _cell_measurement_theta_max 27.4680 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1100 _exptl_absorpt_coefficient_mu 4.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.408 _exptl_absorpt_correction_T_max 0.551 _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12236 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3438 _reflns_number_gt 3323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 2.1c(K.Brandenburg, 1999)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _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^)+(0.0472P)^2^+3.5755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3438 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Er1 Er 0.450679(6) 0.615820(7) 0.052968(13) 0.01888(4) Uani 1 1 d . . . O1 O 0.48943(12) 0.77372(12) 0.0960(2) 0.0326(5) Uani 1 1 d . . . H1W H 0.4894 0.8000 0.0006 0.049 Uiso 1 1 d R . . H2W H 0.4553 0.8006 0.1515 0.049 Uiso 1 1 d R . . O2 O 0.47672(13) 0.39034(12) -0.3337(3) 0.0306(5) Uani 1 1 d . . . O3 O 0.45777(11) 0.50900(12) -0.1693(2) 0.0287(5) Uani 1 1 d . . . O4 O 0.36718(11) 0.49389(12) 0.1077(3) 0.0335(5) Uani 1 1 d . . . O5 O 0.42665(12) 0.35823(14) 0.0512(3) 0.0357(5) Uani 1 1 d . . . O6 O 0.34889(11) 0.67857(12) 0.2038(2) 0.0295(5) Uani 1 1 d . . . O7 O 0.38054(10) 0.81641(12) 0.3245(2) 0.0272(5) Uani 1 1 d . . . N1 N 0.21993(17) 0.11824(15) 0.2579(4) 0.0381(8) Uani 1 1 d . . . N2 N 0.15212(17) 0.11309(16) 0.3271(4) 0.0417(8) Uani 1 1 d . . . N3 N 0.12372(15) 0.19982(17) 0.3518(3) 0.0375(7) Uani 1 1 d . . . H3 H 0.0797 0.2122 0.3961 0.045 Uiso 1 1 calc R . . N4 N 0.01764(16) 0.80566(19) 0.4693(4) 0.0477(8) Uani 1 1 d . . . N5 N 0.01717(17) 0.89688(19) 0.4747(4) 0.0487(9) Uani 1 1 d . . . N6 N 0.08812(14) 0.92837(18) 0.4318(4) 0.0419(7) Uani 1 1 d . . . H6 H 0.1010 0.9867 0.4267 0.050 Uiso 1 1 calc R . . C1 C 0.37387(18) 0.5017(2) -0.4356(4) 0.0373(8) Uani 1 1 d . . . H1A H 0.3804 0.4756 -0.5450 0.056 Uiso 1 1 calc R . . H1B H 0.3771 0.5688 -0.4410 0.056 Uiso 1 1 calc R . . H1C H 0.3217 0.4838 -0.4030 0.056 Uiso 1 1 calc R . . C2 C 0.43942(15) 0.46578(17) -0.3082(3) 0.0232(6) Uani 1 1 d . . . C3 C 0.37013(16) 0.40627(19) 0.1048(4) 0.0267(7) Uani 1 1 d . . . C4 C 0.30169(15) 0.35238(18) 0.1695(3) 0.0244(6) Uani 1 1 d . . . C5 C 0.30211(16) 0.25609(18) 0.1736(3) 0.0277(7) Uani 1 1 d . . . H5 H 0.3442 0.2216 0.1352 0.033 Uiso 1 1 calc R . . C6 C 0.23664(16) 0.21255(19) 0.2378(3) 0.0294(7) Uani 1 1 d . . . C7 C 0.17444(16) 0.26465(19) 0.2967(3) 0.0283(7) Uani 1 1 d . . . C8 C 0.17284(18) 0.3634(2) 0.2922(4) 0.0367(8) Uani 1 1 d . . . H8 H 0.1306 0.3978 0.3303 0.044 Uiso 1 1 calc R . . C9 C 0.23705(17) 0.4053(2) 0.2285(4) 0.0309(7) Uani 1 1 d . . . H9 H 0.2388 0.4704 0.2233 0.037 Uiso 1 1 calc R . . C10 C 0.33115(15) 0.75001(17) 0.2825(3) 0.0226(6) Uani 1 1 d . . . C11 C 0.24606(15) 0.76108(18) 0.3278(3) 0.0250(6) Uani 1 1 d . . . C12 C 0.19797(18) 0.68119(19) 0.3471(4) 0.0351(8) Uani 1 1 d . . . H12 H 0.2192 0.6225 0.3252 0.042 Uiso 1 1 calc R . . C13 C 0.12127(19) 0.6862(2) 0.3968(4) 0.0420(9) Uani 1 1 d . . . H13 H 0.0910 0.6326 0.4136 0.050 Uiso 1 1 calc R . . C14 C 0.09080(17) 0.7761(2) 0.4208(4) 0.0346(7) Uani 1 1 d . . . C15 C 0.13763(17) 0.8555(2) 0.3970(4) 0.0304(7) Uani 1 1 d . . . C16 C 0.21689(16) 0.84946(19) 0.3524(4) 0.0292(7) Uani 1 1 d . . . H16 H 0.2483 0.9026 0.3400 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Er1 0.02089(7) 0.01238(7) 0.02449(7) 0.00011(3) 0.00760(6) 0.00021(3) O1 0.0483(11) 0.0153(9) 0.0380(9) -0.0050(8) 0.0213(9) -0.0075(8) O2 0.0384(11) 0.0248(10) 0.0287(10) -0.0075(7) 0.0043(9) 0.0028(7) O3 0.0381(10) 0.0210(9) 0.0261(8) -0.0037(7) -0.0012(8) 0.0078(8) O4 0.0306(9) 0.0171(9) 0.0565(11) -0.0030(8) 0.0208(9) -0.0057(7) O5 0.0315(9) 0.0183(9) 0.0613(13) -0.0049(9) 0.0233(9) -0.0049(9) O6 0.0317(9) 0.0175(8) 0.0419(10) -0.0082(8) 0.0152(8) 0.0002(7) O7 0.0216(8) 0.0231(9) 0.0373(9) -0.0090(8) 0.0054(8) -0.0059(7) N1 0.0401(14) 0.0228(13) 0.0545(16) 0.0042(10) 0.0195(13) -0.0090(9) N2 0.0401(15) 0.0284(14) 0.0599(18) 0.0063(10) 0.0207(14) -0.0075(10) N3 0.0274(11) 0.0340(13) 0.0537(14) 0.0012(11) 0.0169(11) -0.0039(10) N4 0.0345(13) 0.0348(14) 0.0790(18) -0.0017(13) 0.0288(13) -0.0009(11) N5 0.0293(14) 0.0407(15) 0.081(2) 0.0001(14) 0.0270(14) 0.0018(11) N6 0.0294(11) 0.0258(13) 0.0750(17) 0.0012(12) 0.0253(12) 0.0043(10) C1 0.0394(15) 0.0370(16) 0.0346(14) -0.0013(13) -0.0007(13) 0.0000(13) C2 0.0258(12) 0.0203(12) 0.0251(11) -0.0009(10) 0.0106(10) -0.0052(10) C3 0.0226(12) 0.0205(11) 0.0393(14) -0.0031(11) 0.0135(11) 0.0007(11) C4 0.0256(12) 0.0193(12) 0.0292(12) -0.0012(10) 0.0073(11) -0.0084(10) C5 0.0262(12) 0.0200(12) 0.0399(14) 0.0009(11) 0.0165(11) -0.0012(10) C6 0.0317(13) 0.0232(13) 0.0347(13) 0.0019(11) 0.0107(11) 0.0005(11) C7 0.0286(13) 0.0237(13) 0.0340(13) 0.0048(11) 0.0096(11) -0.0064(11) C8 0.0306(14) 0.0290(14) 0.0532(18) -0.0035(14) 0.0165(14) 0.0036(12) C9 0.0272(13) 0.0224(12) 0.0442(15) -0.0026(12) 0.0083(12) -0.0005(11) C10 0.0232(12) 0.0196(12) 0.0264(11) 0.0010(10) 0.0084(10) 0.0003(9) C11 0.0226(12) 0.0236(12) 0.0304(12) -0.0033(11) 0.0097(10) -0.0002(10) C12 0.0366(15) 0.0173(12) 0.0531(16) -0.0086(12) 0.0131(14) -0.0004(11) C13 0.0361(15) 0.0254(14) 0.0680(19) -0.0031(14) 0.0208(15) -0.0083(12) C14 0.0283(13) 0.0278(14) 0.0511(16) -0.0017(13) 0.0200(12) -0.0046(11) C15 0.0291(13) 0.0211(12) 0.0432(15) 0.0007(12) 0.0136(12) 0.0027(11) C16 0.0254(12) 0.0220(13) 0.0416(14) 0.0007(12) 0.0100(12) -0.0019(11) _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 Er1 O7 2.2558(17) 4_575 ? Er1 O4 2.2897(18) . ? Er1 O5 2.300(2) 3_665 ? Er1 O3 2.3404(18) . ? Er1 O6 2.3444(19) . ? Er1 O1 2.3547(18) . ? Er1 O2 2.409(2) 3_665 ? Er1 O3 2.4479(18) 3_665 ? Er1 C2 2.815(2) 3_665 ? Er1 Er1 3.8163(5) 3_665 ? O1 H1W 0.8431 . ? O1 H2W 0.8442 . ? O2 C2 1.267(3) . ? O2 Er1 2.409(2) 3_665 ? O3 C2 1.268(3) . ? O3 Er1 2.4479(17) 3_665 ? O4 C3 1.250(3) . ? O5 C3 1.268(3) . ? O5 Er1 2.300(2) 3_665 ? O6 C10 1.246(3) . ? O7 C10 1.269(3) . ? O7 Er1 2.2558(17) 4_576 ? N1 N2 1.302(4) . ? N1 C6 1.385(3) . ? N2 N3 1.344(3) . ? N3 C7 1.351(4) . ? N3 H3 0.8600 . ? N4 N5 1.301(4) . ? N4 C14 1.374(4) . ? N5 N6 1.333(4) . ? N6 C15 1.368(4) . ? N6 H6 0.8600 . ? C1 C2 1.487(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 Er1 2.815(2) 3_665 ? C3 C4 1.502(4) . ? C4 C5 1.373(4) . ? C4 C9 1.427(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9300 . ? C6 C7 1.389(4) . ? C7 C8 1.408(4) . ? C8 C9 1.361(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.497(4) . ? C11 C16 1.370(4) . ? C11 C12 1.406(4) . ? C12 C13 1.369(4) . ? C12 H12 0.9300 . ? C13 C14 1.398(4) . ? C13 H13 0.9300 . ? C14 C15 1.396(4) . ? C15 C16 1.395(4) . ? C16 H16 0.9300 . ? 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 O7 Er1 O4 102.17(7) 4_575 . ? O7 Er1 O5 92.15(7) 4_575 3_665 ? O4 Er1 O5 139.70(7) . 3_665 ? O7 Er1 O3 74.87(6) 4_575 . ? O4 Er1 O3 74.32(7) . . ? O5 Er1 O3 73.47(7) 3_665 . ? O7 Er1 O6 84.96(7) 4_575 . ? O4 Er1 O6 73.29(7) . . ? O5 Er1 O6 146.19(7) 3_665 . ? O3 Er1 O6 136.88(6) . . ? O7 Er1 O1 79.27(6) 4_575 . ? O4 Er1 O1 149.09(7) . . ? O5 Er1 O1 70.26(7) 3_665 . ? O3 Er1 O1 134.07(7) . . ? O6 Er1 O1 76.12(7) . . ? O7 Er1 O2 156.29(6) 4_575 3_665 ? O4 Er1 O2 92.64(7) . 3_665 ? O5 Er1 O2 88.22(7) 3_665 3_665 ? O3 Er1 O2 127.56(6) . 3_665 ? O6 Er1 O2 81.67(7) . 3_665 ? O1 Er1 O2 78.56(6) . 3_665 ? O7 Er1 O3 148.68(6) 4_575 3_665 ? O4 Er1 O3 74.73(6) . 3_665 ? O5 Er1 O3 73.75(7) 3_665 3_665 ? O3 Er1 O3 74.33(6) . 3_665 ? O6 Er1 O3 122.23(6) . 3_665 ? O1 Er1 O3 119.59(6) . 3_665 ? O2 Er1 O3 53.30(6) 3_665 3_665 ? O7 Er1 C2 170.57(7) 4_575 3_665 ? O4 Er1 C2 84.49(7) . 3_665 ? O5 Er1 C2 78.50(7) 3_665 3_665 ? O3 Er1 C2 100.92(7) . 3_665 ? O6 Er1 C2 103.49(7) . 3_665 ? O1 Er1 C2 98.50(7) . 3_665 ? O2 Er1 C2 26.64(7) 3_665 3_665 ? O3 Er1 C2 26.74(6) 3_665 3_665 ? O7 Er1 Er1 112.82(5) 4_575 3_665 ? O4 Er1 Er1 70.45(5) . 3_665 ? O5 Er1 Er1 69.27(5) 3_665 3_665 ? O3 Er1 Er1 38.14(4) . 3_665 ? O6 Er1 Er1 142.15(4) . 3_665 ? O1 Er1 Er1 138.01(5) . 3_665 ? O2 Er1 Er1 89.46(4) 3_665 3_665 ? O3 Er1 Er1 36.19(4) 3_665 3_665 ? C2 Er1 Er1 62.83(5) 3_665 3_665 ? Er1 O1 H1W 108.8 . . ? Er1 O1 H2W 108.8 . . ? H1W O1 H2W 109.4 . . ? C2 O2 Er1 94.86(15) . 3_665 ? C2 O3 Er1 160.34(17) . . ? C2 O3 Er1 92.97(15) . 3_665 ? Er1 O3 Er1 105.67(6) . 3_665 ? C3 O4 Er1 136.83(18) . . ? C3 O5 Er1 138.01(18) . 3_665 ? C10 O6 Er1 142.03(17) . . ? C10 O7 Er1 141.96(17) . 4_576 ? N2 N1 C6 107.1(2) . . ? N1 N2 N3 109.8(2) . . ? N2 N3 C7 110.1(2) . . ? N2 N3 H3 124.9 . . ? C7 N3 H3 124.9 . . ? N5 N4 C14 108.9(3) . . ? N4 N5 N6 108.6(3) . . ? N5 N6 C15 110.9(2) . . ? N5 N6 H6 124.5 . . ? C15 N6 H6 124.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O3 C2 O2 118.5(2) . . ? O3 C2 C1 120.5(2) . . ? O2 C2 C1 120.9(2) . . ? O3 C2 Er1 60.29(12) . 3_665 ? O2 C2 Er1 58.50(13) . 3_665 ? C1 C2 Er1 173.22(19) . 3_665 ? O4 C3 O5 125.3(3) . . ? O4 C3 C4 118.2(2) . . ? O5 C3 C4 116.6(2) . . ? C5 C4 C9 121.5(2) . . ? C5 C4 C3 121.2(2) . . ? C9 C4 C3 117.4(2) . . ? C4 C5 C6 116.9(2) . . ? C4 C5 H5 121.5 . . ? C6 C5 H5 121.5 . . ? N1 C6 C7 108.4(2) . . ? N1 C6 C5 130.4(3) . . ? C7 C6 C5 121.2(2) . . ? N3 C7 C6 104.5(2) . . ? N3 C7 C8 132.9(3) . . ? C6 C7 C8 122.6(3) . . ? C9 C8 C7 115.8(3) . . ? C9 C8 H8 122.1 . . ? C7 C8 H8 122.1 . . ? C8 C9 C4 122.1(3) . . ? C8 C9 H9 119.0 . . ? C4 C9 H9 119.0 . . ? O6 C10 O7 124.1(2) . . ? O6 C10 C11 119.0(2) . . ? O7 C10 C11 116.8(2) . . ? C16 C11 C12 121.2(2) . . ? C16 C11 C10 119.0(2) . . ? C12 C11 C10 119.8(2) . . ? C13 C12 C11 122.7(3) . . ? C13 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? C12 C13 C14 116.4(3) . . ? C12 C13 H13 121.8 . . ? C14 C13 H13 121.8 . . ? N4 C14 C15 107.8(3) . . ? N4 C14 C13 131.3(3) . . ? C15 C14 C13 120.8(3) . . ? N6 C15 C14 103.7(2) . . ? N6 C15 C16 134.1(3) . . ? C14 C15 C16 122.2(3) . . ? C11 C16 C15 116.6(3) . . ? C11 C16 H16 121.7 . . ? C15 C16 H16 121.7 . . ? 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 O7 Er1 O3 C2 -24.9(5) 4_575 . . . ? O4 Er1 O3 C2 82.7(5) . . . . ? O5 Er1 O3 C2 -121.8(5) 3_665 . . . ? O6 Er1 O3 C2 40.2(5) . . . . ? O1 Er1 O3 C2 -82.9(5) . . . . ? O2 Er1 O3 C2 163.8(5) 3_665 . . . ? O3 Er1 O3 C2 160.9(6) 3_665 . . . ? C2 Er1 O3 C2 163.8(5) 3_665 . . . ? Er1 Er1 O3 C2 160.9(6) 3_665 . . . ? O7 Er1 O3 Er1 174.24(9) 4_575 . . 3_665 ? O4 Er1 O3 Er1 -78.15(8) . . . 3_665 ? O5 Er1 O3 Er1 77.30(8) 3_665 . . 3_665 ? O6 Er1 O3 Er1 -120.71(8) . . . 3_665 ? O1 Er1 O3 Er1 116.25(9) . . . 3_665 ? O2 Er1 O3 Er1 2.91(11) 3_665 . . 3_665 ? O3 Er1 O3 Er1 0.0 3_665 . . 3_665 ? C2 Er1 O3 Er1 2.90(9) 3_665 . . 3_665 ? O7 Er1 O4 C3 114.5(3) 4_575 . . . ? O5 Er1 O4 C3 6.2(3) 3_665 . . . ? O3 Er1 O4 C3 44.2(3) . . . . ? O6 Er1 O4 C3 -164.7(3) . . . . ? O1 Er1 O4 C3 -156.1(2) . . . . ? O2 Er1 O4 C3 -84.2(3) 3_665 . . . ? O3 Er1 O4 C3 -33.4(3) 3_665 . . . ? C2 Er1 O4 C3 -58.8(3) 3_665 . . . ? Er1 Er1 O4 C3 4.3(3) 3_665 . . . ? O7 Er1 O6 C10 -89.3(3) 4_575 . . . ? O4 Er1 O6 C10 166.4(3) . . . . ? O5 Er1 O6 C10 -2.9(3) 3_665 . . . ? O3 Er1 O6 C10 -150.8(2) . . . . ? O1 Er1 O6 C10 -9.1(3) . . . . ? O2 Er1 O6 C10 71.1(3) 3_665 . . . ? O3 Er1 O6 C10 107.4(3) 3_665 . . . ? C2 Er1 O6 C10 86.5(3) 3_665 . . . ? Er1 Er1 O6 C10 149.3(2) 3_665 . . . ? C6 N1 N2 N3 0.5(3) . . . . ? N1 N2 N3 C7 0.1(3) . . . . ? C14 N4 N5 N6 -0.3(4) . . . . ? N4 N5 N6 C15 -0.1(4) . . . . ? Er1 O3 C2 O2 -167.6(4) . . . . ? Er1 O3 C2 O2 -6.0(2) 3_665 . . . ? Er1 O3 C2 C1 10.6(7) . . . . ? Er1 O3 C2 C1 172.2(2) 3_665 . . . ? Er1 O3 C2 Er1 -161.6(5) . . . 3_665 ? Er1 O2 C2 O3 6.1(2) 3_665 . . . ? Er1 O2 C2 C1 -172.1(2) 3_665 . . . ? Er1 O4 C3 O5 -6.1(5) . . . . ? Er1 O4 C3 C4 173.94(17) . . . . ? Er1 O5 C3 O4 3.1(5) 3_665 . . . ? Er1 O5 C3 C4 -176.95(18) 3_665 . . . ? O4 C3 C4 C5 -178.4(2) . . . . ? O5 C3 C4 C5 1.6(4) . . . . ? O4 C3 C4 C9 0.7(4) . . . . ? O5 C3 C4 C9 -179.3(2) . . . . ? C9 C4 C5 C6 0.0(4) . . . . ? C3 C4 C5 C6 179.1(2) . . . . ? N2 N1 C6 C7 -0.8(3) . . . . ? N2 N1 C6 C5 178.6(3) . . . . ? C4 C5 C6 N1 179.9(3) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? N2 N3 C7 C6 -0.6(3) . . . . ? N2 N3 C7 C8 179.5(3) . . . . ? N1 C6 C7 N3 0.8(3) . . . . ? C5 C6 C7 N3 -178.6(2) . . . . ? N1 C6 C7 C8 -179.3(3) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? N3 C7 C8 C9 178.9(3) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C4 0.3(4) . . . . ? C5 C4 C9 C8 0.2(4) . . . . ? C3 C4 C9 C8 -178.9(3) . . . . ? Er1 O6 C10 O7 -10.9(4) . . . . ? Er1 O6 C10 C11 167.42(18) . . . . ? Er1 O7 C10 O6 -110.9(3) 4_576 . . . ? Er1 O7 C10 C11 70.8(3) 4_576 . . . ? O6 C10 C11 C16 -155.0(2) . . . . ? O7 C10 C11 C16 23.4(3) . . . . ? O6 C10 C11 C12 26.0(4) . . . . ? O7 C10 C11 C12 -155.6(2) . . . . ? C16 C11 C12 C13 -2.4(4) . . . . ? C10 C11 C12 C13 176.6(3) . . . . ? C11 C12 C13 C14 2.7(5) . . . . ? N5 N4 C14 C15 0.5(4) . . . . ? N5 N4 C14 C13 179.8(3) . . . . ? C12 C13 C14 N4 179.9(3) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? N5 N6 C15 C14 0.5(4) . . . . ? N5 N6 C15 C16 -177.7(3) . . . . ? N4 C14 C15 N6 -0.6(3) . . . . ? C13 C14 C15 N6 -180.0(3) . . . . ? N4 C14 C15 C16 177.9(3) . . . . ? C13 C14 C15 C16 -1.5(5) . . . . ? C12 C11 C16 C15 0.0(4) . . . . ? C10 C11 C16 C15 -179.1(2) . . . . ? N6 C15 C16 C11 179.8(3) . . . . ? C14 C15 C16 C11 1.9(4) . . . . ? 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 O1 H2W O7 0.84 1.96 2.756(3) 157.9 . O1 H1W O2 0.84 1.97 2.766(3) 156.9 2_654 N3 H3 N4 0.86 2.04 2.863(4) 159.7 3_566 N3 H3 N5 0.86 2.53 3.148(4) 129.8 3_566 N6 H6 N2 0.86 2.17 2.989(4) 157.8 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.991 _refine_diff_density_min -2.184 _refine_diff_density_rms 0.149 data_Gd _database_code_depnum_ccdc_archive 'CCDC 873844' #TrackingRef 'Gd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 Gd N6 O7' _chemical_formula_weight 558.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.619(9) _cell_length_b 14.447(8) _cell_length_c 8.019(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.614(10) _cell_angle_gamma 90.00 _cell_volume 1912.4(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.940 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 3.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.514 _exptl_absorpt_correction_T_max 0.633 _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12497 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3547 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 2.1c(K.Brandenburg, 1999)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _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^)+(0.0334P)^2^+7.7343P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3547 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _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 0.44915(2) 0.11592(2) 0.05245(5) 0.02608(16) Uani 1 1 d . . . O1 O 0.4877(4) 0.2765(4) 0.0947(8) 0.0430(15) Uani 1 1 d . . . H2W H 0.4809 0.3046 0.0010 0.064 Uiso 1 1 d R . . H1W H 0.4582 0.3013 0.1621 0.064 Uiso 1 1 d R . . O2 O 0.5242(4) 0.1081(4) 0.3361(7) 0.0369(14) Uani 1 1 d . . . O3 O 0.5436(3) -0.0092(4) 0.1739(7) 0.0362(13) Uani 1 1 d . . . O4 O 0.3659(3) -0.0089(4) 0.1068(8) 0.0388(14) Uani 1 1 d . . . O5 O 0.4256(4) -0.1432(4) 0.0508(8) 0.0448(16) Uani 1 1 d . . . O6 O 0.3769(3) 0.1843(4) -0.1795(7) 0.0367(14) Uani 1 1 d . . . O7 O 0.3452(3) 0.3219(4) -0.2980(7) 0.0380(14) Uani 1 1 d . . . N1 N 0.2208(5) -0.3826(5) 0.2574(10) 0.0430(19) Uani 1 1 d . . . N2 N 0.1528(5) -0.3890(5) 0.3283(11) 0.0442(19) Uani 1 1 d . . . N3 N 0.1253(4) -0.3023(5) 0.3525(10) 0.0448(19) Uani 1 1 d . . . H3 H 0.0816 -0.2904 0.3965 0.054 Uiso 1 1 calc R . . N4 N 0.0146(5) 0.1922(5) -0.0338(11) 0.050(2) Uani 1 1 d . . . N5 N 0.0160(5) 0.1010(6) -0.0273(12) 0.052(2) Uani 1 1 d . . . N6 N 0.0874(5) 0.0717(5) -0.0715(10) 0.049(2) Uani 1 1 d . . . H6 H 0.1010 0.0144 -0.0762 0.059 Uiso 1 1 calc R . . C1 C 0.6269(6) -0.0013(6) 0.4394(11) 0.048(2) Uani 1 1 d . . . H1C H 0.6790 0.0125 0.4047 0.071 Uiso 1 1 calc R . . H1A H 0.6213 -0.0671 0.4503 0.071 Uiso 1 1 calc R . . H1B H 0.6223 0.0277 0.5455 0.071 Uiso 1 1 calc R . . C2 C 0.5620(5) 0.0342(5) 0.3115(10) 0.0309(18) Uani 1 1 d . . . C3 C 0.3675(5) -0.0980(5) 0.1082(11) 0.037(2) Uani 1 1 d . . . C4 C 0.3011(5) -0.1490(6) 0.1708(10) 0.0343(19) Uani 1 1 d . . . C5 C 0.3019(5) -0.2445(6) 0.1724(10) 0.0352(19) Uani 1 1 d . . . H5 H 0.3434 -0.2780 0.1322 0.042 Uiso 1 1 calc R . . C6 C 0.2362(5) -0.2893(5) 0.2386(10) 0.0344(19) Uani 1 1 d . . . C7 C 0.1745(5) -0.2363(6) 0.2993(11) 0.038(2) Uani 1 1 d . . . C8 C 0.1736(5) -0.1394(6) 0.2969(11) 0.040(2) Uani 1 1 d . . . H8 H 0.1329 -0.1053 0.3386 0.048 Uiso 1 1 calc R . . C9 C 0.2368(5) -0.0981(6) 0.2291(11) 0.036(2) Uani 1 1 d . . . H9 H 0.2376 -0.0339 0.2211 0.043 Uiso 1 1 calc R . . C10 C 0.3278(5) 0.2500(5) -0.2212(9) 0.0303(18) Uani 1 1 d . . . C11 C 0.2420(5) 0.2382(6) -0.1769(9) 0.0304(18) Uani 1 1 d . . . C12 C 0.1947(5) 0.3178(6) -0.1577(13) 0.045(2) Uani 1 1 d . . . H12 H 0.2156 0.3759 -0.1780 0.055 Uiso 1 1 calc R . . C13 C 0.1177(6) 0.3109(6) -0.1093(12) 0.046(2) Uani 1 1 d . . . H13 H 0.0868 0.3634 -0.0958 0.056 Uiso 1 1 calc R . . C14 C 0.0876(5) 0.2221(6) -0.0810(11) 0.040(2) Uani 1 1 d . . . C15 C 0.1360(5) 0.1438(6) -0.1084(11) 0.0358(19) Uani 1 1 d . . . C16 C 0.2136(5) 0.1497(6) -0.1510(10) 0.0327(18) Uani 1 1 d . . . H16 H 0.2451 0.0974 -0.1618 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.0288(3) 0.0205(2) 0.0305(3) 0.00003(15) 0.00978(17) 0.00050(15) O1 0.063(4) 0.020(3) 0.053(4) -0.007(3) 0.033(3) -0.007(3) O2 0.048(4) 0.032(3) 0.031(3) -0.008(2) 0.004(3) 0.005(3) O3 0.042(3) 0.035(3) 0.030(3) -0.007(3) 0.001(2) 0.010(3) O4 0.036(3) 0.029(3) 0.057(4) -0.001(3) 0.028(3) -0.003(2) O5 0.043(4) 0.026(3) 0.071(5) -0.006(3) 0.029(3) -0.006(3) O6 0.034(3) 0.028(3) 0.050(4) 0.010(3) 0.013(3) 0.008(2) O7 0.041(3) 0.028(3) 0.049(4) 0.007(3) 0.024(3) -0.001(3) N1 0.037(4) 0.034(4) 0.062(5) 0.007(3) 0.019(4) -0.016(3) N2 0.044(5) 0.032(4) 0.060(5) 0.002(3) 0.018(4) -0.008(3) N3 0.030(4) 0.043(5) 0.065(5) 0.005(4) 0.021(4) 0.000(3) N4 0.042(5) 0.042(5) 0.069(6) 0.001(4) 0.021(4) 0.000(4) N5 0.034(5) 0.045(5) 0.082(6) -0.001(4) 0.027(4) -0.001(4) N6 0.041(5) 0.036(4) 0.076(6) 0.001(4) 0.024(4) -0.001(4) C1 0.063(7) 0.040(5) 0.038(5) 0.001(4) -0.004(4) 0.003(5) C2 0.044(5) 0.023(4) 0.027(4) 0.000(3) 0.012(3) -0.005(4) C3 0.031(5) 0.024(4) 0.051(5) -0.021(4) -0.012(4) 0.006(3) C4 0.037(5) 0.024(4) 0.042(5) -0.007(4) 0.009(4) -0.001(4) C5 0.033(5) 0.034(5) 0.040(5) -0.006(4) 0.009(4) 0.003(4) C6 0.035(5) 0.029(4) 0.041(5) 0.000(4) 0.011(4) -0.005(3) C7 0.033(5) 0.041(5) 0.043(5) 0.006(4) 0.013(4) -0.007(4) C8 0.035(5) 0.033(5) 0.054(6) 0.000(4) 0.013(4) 0.000(4) C9 0.040(5) 0.022(4) 0.048(5) -0.003(4) 0.013(4) -0.003(3) C10 0.040(5) 0.032(4) 0.020(4) 0.002(3) 0.005(3) -0.001(4) C11 0.028(4) 0.037(5) 0.028(4) 0.007(3) 0.011(3) 0.004(3) C12 0.036(5) 0.031(5) 0.071(7) 0.004(4) 0.016(4) -0.003(4) C13 0.049(6) 0.022(4) 0.072(7) 0.003(4) 0.025(5) 0.004(4) C14 0.036(5) 0.037(5) 0.050(5) 0.001(4) 0.019(4) -0.004(4) C15 0.035(5) 0.026(4) 0.049(5) 0.000(4) 0.012(4) 0.001(4) C16 0.032(4) 0.028(4) 0.040(5) 0.001(4) 0.013(3) 0.002(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 O6 2.315(6) . ? Gd1 O4 2.345(5) . ? Gd1 O5 2.361(6) 3_655 ? Gd1 O7 2.389(5) 4_566 ? Gd1 O3 2.396(5) 3_655 ? Gd1 O1 2.420(5) . ? Gd1 O2 2.467(6) . ? Gd1 O3 2.515(5) . ? Gd1 Gd1 3.8872(18) 3_655 ? O1 H2W 0.8500 . ? O1 H1W 0.8500 . ? O2 C2 1.266(9) . ? O3 C2 1.275(9) . ? O3 Gd1 2.396(5) 3_655 ? O4 C3 1.287(9) . ? O5 C3 1.292(10) . ? O5 Gd1 2.361(6) 3_655 ? O6 C10 1.272(9) . ? O7 C10 1.258(9) . ? O7 Gd1 2.389(5) 4_565 ? N1 N2 1.325(10) . ? N1 C6 1.384(10) . ? N2 N3 1.355(9) . ? N3 C7 1.357(10) . ? N3 H3 0.8600 . ? N4 N5 1.319(10) . ? N4 C14 1.380(11) . ? N5 N6 1.344(11) . ? N6 C15 1.371(11) . ? N6 H6 0.8600 . ? C1 C2 1.491(11) . ? C1 H1C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C3 C4 1.463(12) . ? C4 C5 1.380(11) . ? C4 C9 1.419(11) . ? C5 C6 1.423(11) . ? C5 H5 0.9300 . ? C6 C7 1.411(12) . ? C7 C8 1.399(12) . ? C8 C9 1.374(12) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.517(11) . ? C11 C16 1.388(11) . ? C11 C12 1.412(11) . ? C12 C13 1.382(12) . ? C12 H12 0.9300 . ? C13 C14 1.405(11) . ? C13 H13 0.9300 . ? C14 C15 1.419(12) . ? C15 C16 1.374(11) . ? C16 H16 0.9300 . ? 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 O6 Gd1 O4 102.4(2) . . ? O6 Gd1 O5 92.5(2) . 3_655 ? O4 Gd1 O5 139.19(19) . 3_655 ? O6 Gd1 O7 84.5(2) . 4_566 ? O4 Gd1 O7 73.70(18) . 4_566 ? O5 Gd1 O7 146.25(19) 3_655 4_566 ? O6 Gd1 O3 74.50(19) . 3_655 ? O4 Gd1 O3 74.2(2) . 3_655 ? O5 Gd1 O3 73.6(2) 3_655 3_655 ? O7 Gd1 O3 136.5(2) 4_566 3_655 ? O6 Gd1 O1 78.9(2) . . ? O4 Gd1 O1 149.75(19) . . ? O5 Gd1 O1 70.1(2) 3_655 . ? O7 Gd1 O1 76.38(19) 4_566 . ? O3 Gd1 O1 133.43(19) 3_655 . ? O6 Gd1 O2 156.97(19) . . ? O4 Gd1 O2 92.3(2) . . ? O5 Gd1 O2 87.6(2) 3_655 . ? O7 Gd1 O2 82.7(2) 4_566 . ? O3 Gd1 O2 127.19(18) 3_655 . ? O1 Gd1 O2 79.5(2) . . ? O6 Gd1 O3 149.35(18) . . ? O4 Gd1 O3 74.4(2) . . ? O5 Gd1 O3 73.7(2) 3_655 . ? O7 Gd1 O3 122.06(19) 4_566 . ? O3 Gd1 O3 75.4(2) 3_655 . ? O1 Gd1 O3 119.4(2) . . ? O2 Gd1 O3 51.92(17) . . ? O6 Gd1 Gd1 113.07(14) . 3_655 ? O4 Gd1 Gd1 70.01(14) . 3_655 ? O5 Gd1 Gd1 69.19(14) 3_655 3_655 ? O7 Gd1 Gd1 142.21(13) 4_566 3_655 ? O3 Gd1 Gd1 38.75(13) 3_655 3_655 ? O1 Gd1 Gd1 137.85(15) . 3_655 ? O2 Gd1 Gd1 88.48(12) . 3_655 ? O3 Gd1 Gd1 36.61(12) . 3_655 ? Gd1 O1 H2W 109.1 . . ? Gd1 O1 H1W 109.3 . . ? H2W O1 H1W 109.5 . . ? C2 O2 Gd1 95.9(5) . . ? C2 O3 Gd1 160.7(5) . 3_655 ? C2 O3 Gd1 93.4(5) . . ? Gd1 O3 Gd1 104.6(2) 3_655 . ? C3 O4 Gd1 139.3(5) . . ? C3 O5 Gd1 139.9(6) . 3_655 ? C10 O6 Gd1 142.0(5) . . ? C10 O7 Gd1 140.9(5) . 4_565 ? N2 N1 C6 107.0(7) . . ? N1 N2 N3 108.4(6) . . ? N2 N3 C7 112.3(7) . . ? N2 N3 H3 123.8 . . ? C7 N3 H3 123.8 . . ? N5 N4 C14 108.1(7) . . ? N4 N5 N6 108.4(7) . . ? N5 N6 C15 112.1(7) . . ? N5 N6 H6 123.9 . . ? C15 N6 H6 123.9 . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C2 O3 118.3(7) . . ? O2 C2 C1 121.1(7) . . ? O3 C2 C1 120.6(7) . . ? O4 C3 O5 121.2(8) . . ? O4 C3 C4 119.3(7) . . ? O5 C3 C4 119.4(7) . . ? C5 C4 C9 121.4(8) . . ? C5 C4 C3 120.0(7) . . ? C9 C4 C3 118.6(7) . . ? C4 C5 C6 116.8(8) . . ? C4 C5 H5 121.6 . . ? C6 C5 H5 121.6 . . ? N1 C6 C7 109.9(7) . . ? N1 C6 C5 130.1(8) . . ? C7 C6 C5 120.0(7) . . ? N3 C7 C8 134.5(8) . . ? N3 C7 C6 102.4(7) . . ? C8 C7 C6 123.0(8) . . ? C9 C8 C7 115.6(8) . . ? C9 C8 H8 122.2 . . ? C7 C8 H8 122.2 . . ? C8 C9 C4 123.0(8) . . ? C8 C9 H9 118.5 . . ? C4 C9 H9 118.5 . . ? O7 C10 O6 124.6(8) . . ? O7 C10 C11 118.8(7) . . ? O6 C10 C11 116.5(7) . . ? C16 C11 C12 122.0(7) . . ? C16 C11 C10 119.0(7) . . ? C12 C11 C10 119.0(7) . . ? C13 C12 C11 121.1(8) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 118.0(8) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? N4 C14 C13 132.1(8) . . ? N4 C14 C15 108.9(8) . . ? C13 C14 C15 118.9(8) . . ? N6 C15 C16 133.9(8) . . ? N6 C15 C14 102.4(7) . . ? C16 C15 C14 123.6(8) . . ? C15 C16 C11 116.1(7) . . ? C15 C16 H16 121.9 . . ? C11 C16 H16 121.9 . . ? 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 N6 H6 N2 0.86 2.18 2.998(11) 158.5 4 N3 H3 N5 0.86 2.57 3.193(11) 130.5 2_545 N3 H3 N4 0.86 2.06 2.882(11) 160.0 2_545 O1 H1W O6 0.85 1.97 2.785(8) 160.7 4_566 O1 H2W O2 0.85 2.02 2.782(8) 148.9 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.024 _refine_diff_density_min -1.629 _refine_diff_density_rms 0.166