# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/199 data_1 _audit_creation_method SHELXL-97 #*********************************************************************** # 1. Data block for start identification : #*********************************************************************** # 2. Person Making Publication : _publ_contact_author ' Claude Picard' _publ_contact_author_fax '(33) (0) 5 61 55 20 03 ' _publ_contact_author_email 'picard@iris.ups-toulouse.fr' _publ_requested_journal ' Chemical Communications' #*********************************************************************** _chemical_formula_sum 'C 15 H 18 N 3 O 9 Tb' _chemical_formula_weight 543.25 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3087(11) _cell_length_b 11.7069(19) _cell_length_c 13.559(2) _cell_angle_alpha 103.736(19) _cell_angle_beta 100.89(2) _cell_angle_gamma 104.556(19) _cell_volume 908.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2)K _cell_measurement_reflns_used 5000 _cell_measurement_2theta_min 5.4 _cell_measurement_2theta_max 56.2 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4mm _exptl_crystal_size_mid 0.4mm _exptl_crystal_size_min 0.2mm _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 3.950mm _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.565 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_process_details ; Absorption corrections were applied on the data by using a set of symmetry equivalent reflections selected with the criterion [I>30(I)] such that all directions of the reciprocal space are equally represented. Starting from an initial crystal description, the program applies numerical absorption correction to the given set of reflection data as depicted above and calculates the merging R-factor Rint.Procedure is repeated until Rint does not change any more. ; _exptl_special_details ; The data was collected at low temperature (T=140K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was chosen to be 60mm, 167 exposures were obtained and with the crystal rotated through. Coverage of the unique set was 93% complete to at least 28.2\'b0. Crystal decay was monitored by measuring 200 reflections by image. The final unit cell parameters was obtained by the least-squares refinement of 5000 reflections. Only satistical fluctuations were observed in the intensity monitors over the course of the data collection. ; _diffrn_ambient_temperature 140(2)K _diffrn_radiation_wavelength 0.71073\'c5 _diffrn_radiation_type MoK _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; _diffrn_measurement_method rotation _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7818 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2882 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _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^)+(0.0333P)^2^+0.9249P] 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 2882 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0525 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.67595(2) 0.274512(12) 0.350535(10) 0.01017(8) Uani 1 1 d . . . O1 O 1.0268(4) 0.3068(2) 0.47685(18) 0.0157(5) Uani 1 1 d . . . O2 O 0.6455(4) 0.1530(3) 0.4624(2) 0.0337(7) Uani 1 1 d . . . O3 O 0.9741(4) 0.4352(2) 0.33787(18) 0.0163(5) Uani 1 1 d . . . O4 O 0.5600(4) 0.3824(2) 0.2331(2) 0.0233(6) Uani 1 1 d . . . O5 O 0.8526(4) 0.1685(2) 0.23673(18) 0.0180(5) Uani 1 1 d . . . O6 O 0.4246(4) 0.0915(2) 0.22191(19) 0.0191(5) Uani 1 1 d . . . O7 O 0.2976(4) 0.2538(2) 0.3544(2) 0.0195(5) Uani 1 1 d . . . H701 H 0.233(9) 0.276(5) 0.394(4) 0.036(15) Uiso 1 1 d . . . H702 H 0.184(9) 0.216(4) 0.308(4) 0.025(11) Uiso 1 1 d . . . O8 O 0.6784(6) 0.4453(4) 0.4943(3) 0.0324(8) Uani 1 1 d . . . H801 H 0.761(9) 0.467(4) 0.544(4) 0.020(12) Uiso 1 1 d . . . H802 H 0.648(15) 0.482(8) 0.491(7) 0.08(4) Uiso 1 1 d . . . N1 N 1.0286(5) 0.2321(3) 0.5356(2) 0.0207(6) Uani 1 1 d . . . N2 N 0.9305(5) 0.4928(3) 0.2666(2) 0.0197(6) Uani 1 1 d . . . N3 N 0.7273(5) 0.0565(2) 0.1680(2) 0.0145(6) Uani 1 1 d . . . C1 C 0.8250(6) 0.1515(3) 0.5288(3) 0.0161(7) Uani 1 1 d . . . C2 C 0.8150(8) 0.0695(4) 0.5868(3) 0.0388(11) Uani 1 1 d . . . H2 H 0.6731 0.0129 0.5818 0.047 Uiso 1 1 calc R . . C3 C 1.2148(8) 0.1516(5) 0.6588(4) 0.0478(13) Uani 1 1 d . . . H3 H 1.3499 0.1520 0.7041 0.057 Uiso 1 1 calc R . . C4 C 1.0080(9) 0.0696(4) 0.6513(4) 0.0486(14) Uani 1 1 d . . . H4 H 1.0007 0.0130 0.6915 0.058 Uiso 1 1 calc R . . C5 C 1.2229(7) 0.2320(4) 0.6005(3) 0.0326(10) Uani 1 1 d . . . H5 H 1.3646 0.2884 0.6050 0.039 Uiso 1 1 calc R . . C6 C 1.1020(8) 0.5749(4) 0.2481(4) 0.0357(10) Uani 1 1 d . . . H6 H 1.2540 0.5929 0.2877 0.043 Uiso 1 1 calc R . . C7 C 0.6625(8) 0.5222(4) 0.1360(4) 0.0386(11) Uani 1 1 d . . . H7 H 0.5102 0.5045 0.0968 0.046 Uiso 1 1 calc R . . C8 C 1.0572(9) 0.6308(4) 0.1739(4) 0.0497(13) Uani 1 1 d . . . H8 H 1.1775 0.6872 0.1604 0.060 Uiso 1 1 calc R . . C9 C 0.8355(10) 0.6056(5) 0.1176(4) 0.0510(14) Uani 1 1 d . . . H9 H 0.8026 0.6459 0.0662 0.061 Uiso 1 1 calc R . . C10 C 0.7093(6) 0.4638(3) 0.2118(3) 0.0187(7) Uani 1 1 d . . . C11 C 0.4998(5) 0.0191(3) 0.1629(2) 0.0133(6) Uani 1 1 d . . . C12 C 0.3728(6) -0.0976(3) 0.0908(3) 0.0215(8) Uani 1 1 d . . . H12 H 0.2151 -0.1285 0.0848 0.026 Uiso 1 1 calc R . . C13 C 0.7044(7) -0.1228(3) 0.0378(3) 0.0223(8) Uani 1 1 d . . . H13 H 0.7741 -0.1703 -0.0047 0.027 Uiso 1 1 calc R . . C14 C 0.4695(7) -0.1671(3) 0.0296(3) 0.0232(8) Uani 1 1 d . . . H14 H 0.3796 -0.2453 -0.0187 0.028 Uiso 1 1 calc R . . C15 C 0.8286(6) -0.0104(3) 0.1084(3) 0.0188(7) Uani 1 1 d . . . H15 H 0.9867 0.0210 0.1155 0.023 Uiso 1 1 calc R . . O9 O 0.0931(5) 0.3032(3) 0.1157(2) 0.0259(6) Uani 1 1 d . . . H901 H 0.033(10) 0.278(5) 0.154(4) 0.040(15) Uiso 1 1 d . . . H902 H 0.226(11) 0.324(5) 0.155(5) 0.045(15) 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 Tb1 0.00839(10) 0.01068(10) 0.01174(10) 0.00402(7) 0.00263(7) 0.00285(7) O1 0.0148(11) 0.0182(11) 0.0179(11) 0.0100(10) 0.0047(10) 0.0069(9) O2 0.0157(13) 0.0424(16) 0.0412(16) 0.0320(14) -0.0041(12) -0.0039(12) O3 0.0147(11) 0.0168(11) 0.0160(11) 0.0073(9) 0.0015(9) 0.0019(9) O4 0.0168(12) 0.0277(13) 0.0258(13) 0.0163(11) 0.0007(11) 0.0036(10) O5 0.0137(11) 0.0149(11) 0.0186(11) -0.0012(9) 0.0023(10) 0.0001(9) O6 0.0146(11) 0.0184(12) 0.0230(12) 0.0025(10) 0.0058(10) 0.0055(10) O7 0.0079(12) 0.0271(14) 0.0176(12) -0.0027(11) 0.0026(12) 0.0048(11) O8 0.0207(15) 0.0434(19) 0.0224(16) -0.0114(14) -0.0059(13) 0.0203(14) N1 0.0200(15) 0.0194(15) 0.0196(14) 0.0068(12) -0.0001(13) 0.0037(12) N2 0.0229(15) 0.0139(13) 0.0194(14) 0.0072(12) 0.0036(13) 0.0000(12) N3 0.0163(14) 0.0115(13) 0.0121(13) 0.0010(11) -0.0005(11) 0.0035(11) C1 0.0135(15) 0.0179(16) 0.0143(15) 0.0130(13) -0.0037(13) -0.0019(13) C2 0.041(2) 0.032(2) 0.032(2) 0.0230(19) -0.0049(19) -0.0095(19) C3 0.040(3) 0.044(3) 0.046(3) 0.025(2) -0.020(2) 0.001(2) C4 0.059(3) 0.036(2) 0.036(2) 0.026(2) -0.018(2) -0.003(2) C5 0.0208(19) 0.032(2) 0.038(2) 0.0168(19) -0.0071(17) 0.0024(16) C6 0.031(2) 0.030(2) 0.037(2) 0.0145(19) 0.0046(19) -0.0069(18) C7 0.046(3) 0.034(2) 0.034(2) 0.023(2) -0.003(2) 0.008(2) C8 0.057(3) 0.035(2) 0.050(3) 0.028(2) 0.009(2) -0.010(2) C9 0.070(3) 0.037(2) 0.043(3) 0.029(2) 0.002(3) 0.005(2) C10 0.0219(17) 0.0159(16) 0.0173(16) 0.0079(14) 0.0006(14) 0.0050(14) C11 0.0139(15) 0.0120(15) 0.0143(15) 0.0057(13) 0.0018(13) 0.0044(13) C12 0.0176(17) 0.0158(16) 0.0260(18) 0.0060(15) -0.0011(15) 0.0021(14) C13 0.033(2) 0.0194(17) 0.0176(17) 0.0046(14) 0.0042(16) 0.0155(15) C14 0.034(2) 0.0103(16) 0.0182(16) -0.0022(13) -0.0020(16) 0.0078(15) C15 0.0233(17) 0.0238(18) 0.0161(16) 0.0087(14) 0.0090(15) 0.0137(15) O9 0.0240(15) 0.0338(15) 0.0208(13) 0.0093(12) 0.0064(13) 0.0090(12) _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 O2 2.315(2) . ? Tb1 O7 2.350(3) . ? Tb1 O5 2.366(2) . ? Tb1 O3 2.368(2) . ? Tb1 O6 2.370(2) . ? Tb1 O4 2.376(2) . ? Tb1 O1 2.411(2) . ? Tb1 O8 2.434(3) . ? O1 N1 1.315(4) . ? O2 C1 1.313(4) . ? O3 N2 1.328(4) . ? O4 C10 1.289(4) . ? O5 N3 1.354(4) . ? O6 C11 1.268(4) . ? O7 H701 0.77(6) . ? O7 H702 0.80(5) . ? O8 H801 0.71(5) . ? O8 H802 0.52(7) . ? N1 C1 1.362(5) . ? N1 C5 1.368(5) . ? N2 C6 1.360(5) . ? N2 C10 1.366(5) . ? N3 C15 1.349(5) . ? N3 C11 1.374(4) . ? C1 C2 1.375(5) . ? C2 C4 1.358(6) . ? C2 H2 0.9500 . ? C3 C5 1.363(6) . ? C3 C4 1.382(7) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C8 1.350(6) . ? C6 H6 0.9500 . ? C7 C9 1.375(7) . ? C7 C10 1.389(5) . ? C7 H7 0.9500 . ? C8 C9 1.381(8) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.408(5) . ? C12 C14 1.358(6) . ? C12 H12 0.9500 . ? C13 C15 1.365(5) . ? C13 C14 1.414(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O9 H901 0.76(6) . ? O9 H902 0.84(6) . ? 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 O2 Tb1 O7 81.44(10) . . ? O2 Tb1 O5 99.46(10) . . ? O7 Tb1 O5 134.50(9) . . ? O2 Tb1 O3 134.13(8) . . ? O7 Tb1 O3 133.69(9) . . ? O5 Tb1 O3 76.48(8) . . ? O2 Tb1 O6 83.62(10) . . ? O7 Tb1 O6 69.09(9) . . ? O5 Tb1 O6 65.87(8) . . ? O3 Tb1 O6 131.14(8) . . ? O2 Tb1 O4 158.38(10) . . ? O7 Tb1 O4 77.07(9) . . ? O5 Tb1 O4 94.00(9) . . ? O3 Tb1 O4 65.55(8) . . ? O6 Tb1 O4 86.58(9) . . ? O2 Tb1 O1 65.50(8) . . ? O7 Tb1 O1 136.03(9) . . ? O5 Tb1 O1 81.25(8) . . ? O3 Tb1 O1 68.76(8) . . ? O6 Tb1 O1 130.26(8) . . ? O4 Tb1 O1 133.87(8) . . ? O2 Tb1 O8 87.81(14) . . ? O7 Tb1 O8 72.20(11) . . ? O5 Tb1 O8 152.92(10) . . ? O3 Tb1 O8 79.78(11) . . ? O6 Tb1 O8 141.17(10) . . ? O4 Tb1 O8 87.84(13) . . ? O1 Tb1 O8 78.14(11) . . ? N1 O1 Tb1 118.04(19) . . ? C1 O2 Tb1 121.7(2) . . ? N2 O3 Tb1 118.93(18) . . ? C10 O4 Tb1 120.2(2) . . ? N3 O5 Tb1 118.20(19) . . ? C11 O6 Tb1 120.7(2) . . ? Tb1 O7 H701 138(4) . . ? Tb1 O7 H702 128(3) . . ? H701 O7 H702 94(5) . . ? Tb1 O8 H801 122(4) . . ? Tb1 O8 H802 127(10) . . ? H801 O8 H802 106(10) . . ? O1 N1 C1 116.9(3) . . ? O1 N1 C5 123.1(3) . . ? C1 N1 C5 120.0(3) . . ? O3 N2 C6 120.6(3) . . ? O3 N2 C10 117.4(3) . . ? C6 N2 C10 122.0(3) . . ? C15 N3 O5 119.4(3) . . ? C15 N3 C11 124.1(3) . . ? O5 N3 C11 116.6(3) . . ? O2 C1 N1 117.2(3) . . ? O2 C1 C2 122.8(3) . . ? N1 C1 C2 120.0(3) . . ? C4 C2 C1 120.0(4) . . ? C4 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C5 C3 C4 119.3(4) . . ? C5 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C2 C4 C3 120.3(4) . . ? C2 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C3 C5 N1 120.5(4) . . ? C3 C5 H5 119.7 . . ? N1 C5 H5 119.7 . . ? C8 C6 N2 120.3(4) . . ? C8 C6 H6 119.8 . . ? N2 C6 H6 119.8 . . ? C9 C7 C10 120.3(4) . . ? C9 C7 H7 119.9 . . ? C10 C7 H7 119.9 . . ? C6 C8 C9 119.6(4) . . ? C6 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C7 C9 C8 120.0(4) . . ? C7 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? O4 C10 N2 117.3(3) . . ? O4 C10 C7 124.9(3) . . ? N2 C10 C7 117.8(3) . . ? O6 C11 N3 117.9(3) . . ? O6 C11 C12 126.5(3) . . ? N3 C11 C12 115.6(3) . . ? C14 C12 C11 121.9(3) . . ? C14 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C15 C13 C14 118.5(4) . . ? C15 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C12 C14 C13 119.8(3) . . ? C12 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? N3 C15 C13 120.2(3) . . ? N3 C15 H15 119.9 . . ? C13 C15 H15 119.9 . . ? H901 O9 H902 95(5) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.701 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.111