# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1381 data_s1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5-N,N',N''-tris(2-methoxyethyl)trimesic amide ; _chemical_name_common ? _chemical_melting_point 150 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 N3 O6' _chemical_formula_weight 381.43 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.776(7) _cell_length_b 7.241(6) _cell_length_c 13.028(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.84(5) _cell_angle_gamma 90.00 _cell_volume 1011.4(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9722 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC6S' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1944 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1944 _reflns_number_gt 1337 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0817P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 1944 _refine_ls_number_parameters 271 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1138 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1629 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O13 O 1.2741(4) -0.0091(7) 0.8571(3) 0.0652(12) Uani 1 1 d . . . O17A O 1.4269(6) 0.5271(9) 0.8545(4) 0.078(2) Uani 0.782(12) 1 d PD A 1 O17B O 1.556(2) 0.468(3) 0.8156(18) 0.090(10) Uani 0.218(12) 1 d PD A 2 O19 O 1.0623(4) 0.0205(6) 1.2778(3) 0.0613(11) Uani 1 1 d . . . O23 O 0.9205(5) 0.5380(6) 1.3793(4) 0.0741(13) Uani 1 1 d . . . O7 O 0.7043(3) -0.0158(5) 0.8673(3) 0.0526(10) Uani 1 1 d . . . O11 O 0.6589(5) 0.0052(8) 0.5147(3) 0.0887(16) Uani 1 1 d . . . N14 N 1.3390(4) 0.2204(7) 0.9680(3) 0.0495(11) Uani 1 1 d . . . H14 H 1.3198 0.2905 1.0173 0.059 Uiso 1 1 calc R . . N20 N 0.8946(4) 0.2073(7) 1.2551(3) 0.0489(11) Uani 1 1 d . . . H20 H 0.8442 0.2669 1.2115 0.059 Uiso 1 1 calc R . . N8 N 0.7932(4) 0.1898(7) 0.7660(3) 0.0503(11) Uani 1 1 d . . . H8 H 0.8511 0.2708 0.7630 0.060 Uiso 1 1 calc R . . C2 C 1.0230(5) 0.1035(7) 0.8962(4) 0.0411(11) Uani 1 1 d . . . H2 H 1.0321 0.1017 0.8259 0.049 Uiso 1 1 calc R . . C3 C 1.1277(4) 0.1053(7) 0.9665(4) 0.0397(11) Uani 1 1 d . . . C13 C 1.2532(5) 0.0997(8) 0.9269(4) 0.0464(12) Uani 1 1 d . . . C15 C 1.4609(5) 0.2387(9) 0.9340(4) 0.0574(16) Uani 1 1 d . A . H15A H 1.4917 0.1166 0.9195 0.069 Uiso 1 1 calc R . . H15B H 1.5164 0.2904 0.9900 0.069 Uiso 1 1 calc R . . C16 C 1.4671(8) 0.3553(12) 0.8414(7) 0.094(3) Uani 1 1 d D . . H16A H 1.5526 0.3598 0.8245 0.113 Uiso 0.782(12) 1 calc PR A 1 H16B H 1.4168 0.2994 0.7836 0.113 Uiso 0.782(12) 1 calc PR A 1 H16C H 1.4534 0.2703 0.7839 0.113 Uiso 0.218(12) 1 calc PR A 2 H16D H 1.3927 0.4315 0.8384 0.113 Uiso 0.218(12) 1 calc PR A 2 C18B C 1.542(6) 0.609(6) 0.743(3) 0.12(2) Uani 0.218(12) 1 d PD A 2 H18A H 1.4571 0.6135 0.7134 0.186 Uiso 0.218(12) 1 calc PR A 2 H18B H 1.5959 0.5863 0.6904 0.186 Uiso 0.218(12) 1 calc PR A 2 H18C H 1.5640 0.7247 0.7764 0.186 Uiso 0.218(12) 1 calc PR A 2 C18A C 1.4540(13) 0.6492(14) 0.7744(8) 0.088(4) Uani 0.782(12) 1 d PD A 1 H18D H 1.5427 0.6586 0.7734 0.132 Uiso 0.782(12) 1 calc PR A 1 H18E H 1.4201 0.7690 0.7864 0.132 Uiso 0.782(12) 1 calc PR A 1 H18F H 1.4173 0.6025 0.7093 0.132 Uiso 0.782(12) 1 calc PR A 1 C4 C 1.1144(5) 0.1110(7) 1.0719(4) 0.0427(12) Uani 1 1 d . . . H4 H 1.1847 0.1141 1.1196 0.051 Uiso 1 1 calc R . . C5 C 0.9949(5) 0.1119(7) 1.1059(4) 0.0412(12) Uani 1 1 d . . . C19 C 0.9864(5) 0.1099(9) 1.2204(4) 0.0458(12) Uani 1 1 d . . . C21 C 0.8764(7) 0.2164(9) 1.3638(4) 0.0614(17) Uani 1 1 d . . . H21A H 0.9550 0.1920 1.4047 0.074 Uiso 1 1 calc R . . H21B H 0.8175 0.1218 1.3796 0.074 Uiso 1 1 calc R . . C22 C 0.8279(7) 0.4039(9) 1.3925(5) 0.0642(18) Uani 1 1 d . . . H22A H 0.7522 0.4331 1.3488 0.077 Uiso 1 1 calc R . . H22B H 0.8089 0.4030 1.4637 0.077 Uiso 1 1 calc R . . C24 C 0.8758(9) 0.7200(11) 1.3939(7) 0.106(3) Uani 1 1 d . . . H24A H 0.8061 0.7446 1.3438 0.159 Uiso 1 1 calc R . . H24B H 0.9410 0.8073 1.3857 0.159 Uiso 1 1 calc R . . H24C H 0.8500 0.7308 1.4621 0.159 Uiso 1 1 calc R . . C6 C 0.8911(5) 0.1093(7) 1.0342(4) 0.0419(12) Uani 1 1 d . . . H6 H 0.8118 0.1110 1.0564 0.050 Uiso 1 1 calc R . . C1 C 0.9044(4) 0.1042(8) 0.9285(4) 0.0404(12) Uani 1 1 d . . . C7 C 0.7912(5) 0.0875(8) 0.8524(4) 0.0439(12) Uani 1 1 d . . . C9 C 0.7012(6) 0.1672(9) 0.6785(4) 0.0592(16) Uani 1 1 d . . . H9A H 0.6880 0.2843 0.6430 0.071 Uiso 1 1 calc R . . H9B H 0.6226 0.1292 0.7022 0.071 Uiso 1 1 calc R . . C10 C 0.7427(6) 0.0252(11) 0.6054(5) 0.0694(18) Uani 1 1 d . . . H10A H 0.8241 0.0598 0.5860 0.083 Uiso 1 1 calc R . . H10B H 0.7512 -0.0929 0.6406 0.083 Uiso 1 1 calc R . . C12 C 0.5641(9) -0.1213(17) 0.5259(7) 0.130(4) Uani 1 1 d . . . H12A H 0.6000 -0.2382 0.5473 0.194 Uiso 1 1 calc R . . H12B H 0.5140 -0.1358 0.4612 0.194 Uiso 1 1 calc R . . H12C H 0.5130 -0.0774 0.5769 0.194 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 O13 0.069(3) 0.055(3) 0.075(3) -0.025(3) 0.022(2) -0.009(2) O17A 0.096(5) 0.062(4) 0.078(4) 0.000(4) 0.026(3) 0.010(4) O17B 0.086(17) 0.088(19) 0.100(17) 0.018(15) 0.029(13) -0.043(15) O19 0.086(3) 0.049(2) 0.048(2) 0.004(2) 0.0037(19) 0.022(2) O23 0.095(3) 0.039(2) 0.091(3) -0.009(2) 0.026(3) 0.000(2) O7 0.053(2) 0.039(2) 0.066(2) 0.009(2) 0.0045(18) -0.007(2) O11 0.109(4) 0.087(4) 0.066(3) -0.007(3) -0.010(3) -0.025(3) N14 0.048(2) 0.038(3) 0.063(3) -0.011(2) 0.011(2) 0.000(2) N20 0.064(3) 0.038(3) 0.046(2) 0.005(2) 0.011(2) 0.010(3) N8 0.060(3) 0.040(3) 0.050(2) 0.006(2) 0.001(2) -0.008(2) C2 0.056(3) 0.024(2) 0.044(3) -0.005(3) 0.010(2) -0.004(3) C3 0.050(3) 0.021(2) 0.048(3) -0.003(3) 0.007(2) -0.002(3) C13 0.055(3) 0.035(3) 0.048(3) 0.001(3) 0.003(2) 0.004(3) C15 0.050(3) 0.050(4) 0.074(4) -0.003(3) 0.015(3) -0.005(3) C16 0.102(6) 0.074(6) 0.113(6) -0.009(5) 0.045(5) -0.015(5) C18B 0.23(6) 0.08(3) 0.08(2) -0.01(3) 0.08(3) -0.05(4) C18A 0.130(10) 0.065(7) 0.071(6) 0.023(5) 0.023(6) 0.015(6) C4 0.056(3) 0.022(2) 0.050(3) -0.002(3) 0.003(2) 0.001(3) C5 0.053(3) 0.019(2) 0.052(3) 0.001(3) 0.009(3) -0.001(3) C19 0.058(3) 0.034(3) 0.046(3) 0.001(3) 0.005(3) -0.004(3) C21 0.094(5) 0.038(3) 0.056(3) 0.005(3) 0.024(3) 0.008(3) C22 0.087(5) 0.044(4) 0.067(4) 0.000(3) 0.034(4) 0.008(3) C24 0.147(8) 0.041(4) 0.131(7) -0.014(5) 0.025(6) 0.005(5) C6 0.046(3) 0.024(2) 0.057(3) -0.005(3) 0.013(2) -0.003(3) C1 0.052(3) 0.022(2) 0.047(3) 0.003(3) 0.006(2) -0.008(3) C7 0.051(3) 0.027(3) 0.055(3) -0.004(3) 0.010(2) 0.004(3) C9 0.069(4) 0.055(4) 0.052(3) 0.009(3) -0.002(3) 0.004(3) C10 0.071(4) 0.076(5) 0.060(4) -0.003(4) -0.003(3) 0.000(4) C12 0.133(8) 0.120(10) 0.127(8) 0.002(7) -0.026(6) -0.042(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O13 C13 1.242(7) . ? O17A C16 1.333(10) . ? O17A C18A 1.421(11) . ? O17B C16 1.328(18) . ? O17B C18B 1.38(3) . ? O19 C19 1.234(6) . ? O23 C22 1.415(8) . ? O23 C24 1.422(10) . ? O7 C7 1.229(6) . ? O11 C12 1.391(11) . ? O11 C10 1.419(7) . ? N14 C13 1.343(7) . ? N14 C15 1.435(6) . ? N20 C19 1.332(7) . ? N20 C21 1.451(7) . ? N8 C7 1.350(7) . ? N8 C9 1.442(7) . ? C2 C3 1.380(7) . ? C2 C1 1.386(7) . ? C3 C4 1.396(7) . ? C3 C13 1.496(7) . ? C15 C16 1.479(10) . ? C4 C5 1.404(7) . ? C5 C6 1.382(7) . ? C5 C19 1.503(7) . ? C21 C22 1.515(9) . ? C6 C1 1.399(7) . ? C1 C7 1.497(7) . ? C9 C10 1.500(9) . ? 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 C16 O17A C18A 113.1(7) . . ? C16 O17B C18B 127(3) . . ? C22 O23 C24 111.5(6) . . ? C12 O11 C10 113.1(6) . . ? C13 N14 C15 123.5(4) . . ? C19 N20 C21 122.3(5) . . ? C7 N8 C9 121.9(5) . . ? C3 C2 C1 121.0(5) . . ? C2 C3 C4 119.6(5) . . ? C2 C3 C13 118.6(4) . . ? C4 C3 C13 121.8(4) . . ? O13 C13 N14 122.4(5) . . ? O13 C13 C3 120.5(5) . . ? N14 C13 C3 117.1(5) . . ? N14 C15 C16 115.0(6) . . ? O17A C16 O17B 73.1(13) . . ? O17A C16 C15 112.7(7) . . ? O17B C16 C15 130.7(13) . . ? C3 C4 C5 120.0(5) . . ? C6 C5 C4 119.4(5) . . ? C6 C5 C19 123.0(5) . . ? C4 C5 C19 117.6(4) . . ? O19 C19 N20 122.8(5) . . ? O19 C19 C5 120.2(5) . . ? N20 C19 C5 117.0(5) . . ? N20 C21 C22 111.4(5) . . ? O23 C22 C21 108.7(5) . . ? C5 C6 C1 120.6(5) . . ? C2 C1 C6 119.3(5) . . ? C2 C1 C7 120.8(4) . . ? C6 C1 C7 119.7(4) . . ? O7 C7 N8 122.9(5) . . ? O7 C7 C1 121.8(5) . . ? N8 C7 C1 115.3(5) . . ? N8 C9 C10 110.7(5) . . ? O11 C10 C9 113.2(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.246 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.071