Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Rik Van Deun' 'Koen Binnemans' 'Bertrand Donnio' 'D. Guillon' 'Tatjana N. Parac-Vogt' ; K.V.Hecke ; 'Luc Van Meervelt' _publ_contact_author_name 'Dr Rik Van Deun' _publ_contact_author_address ; Department of Chemistry K.U.Leuven Celestijnenlaan 200F Heverlee 3001 BELGIUM ; _publ_contact_author_email RIK.VANDEUN@CHEM.KULEUVEN.AC.BE _publ_section_title ; Liquid-crystalline azines formed by the rare-earth promoted decomposition of hydrazide habbe ligands: structural and thermal properties ; data_wg15 _database_code_CSD 201672 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H44 N2 O4' _chemical_formula_sum 'C30 H44 N2 O4' _chemical_formula_weight 496.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6139(5) _cell_length_b 11.0646(12) _cell_length_c 11.2402(11) _cell_angle_alpha 92.489(8) _cell_angle_beta 91.835(6) _cell_angle_gamma 101.208(7) _cell_volume 683.65(12) _cell_formula_units_Z 1 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 270 _exptl_absorpt_coefficient_mu 0.627 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7875 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Goebel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2555 _diffrn_reflns_av_R_equivalents 0.1049 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 71.12 _reflns_number_total 2555 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLUTON _computing_publication_material 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^)+(0.1554P)^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 SHELXL _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^ _refine_ls_number_reflns 2555 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1986 _refine_ls_wR_factor_gt 0.1847 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 N1 N -0.9004(2) 0.04867(12) 0.00424(12) 0.0132(4) Uani 1 1 d . . . C2 C -0.9274(3) 0.13877(15) 0.07652(14) 0.0123(4) Uani 1 1 d . . . H2 H -1.088(3) 0.13315(18) 0.1209(9) 0.015 Uiso 1 1 calc R . . C3 C -0.7374(3) 0.24717(14) 0.09628(14) 0.0102(4) Uani 1 1 d . . . C4 C -0.5141(3) 0.25955(14) 0.03763(13) 0.0111(4) Uani 1 1 d . . . C5 C -0.3364(3) 0.36491(14) 0.05741(13) 0.0118(4) Uani 1 1 d . . . H5 H -0.191(3) 0.3729(2) 0.0175(9) 0.014 Uiso 1 1 calc R . . C6 C -0.3734(3) 0.45909(14) 0.13667(14) 0.0109(4) Uani 1 1 d . . . C7 C -0.5914(3) 0.44959(14) 0.19572(14) 0.0127(4) Uani 1 1 d . . . H7 H -0.6175(6) 0.5151(14) 0.2506(12) 0.015 Uiso 1 1 calc R . . C8 C -0.7691(3) 0.34439(14) 0.17396(14) 0.0124(4) Uani 1 1 d . . . H8 H -0.919(3) 0.3380(2) 0.2136(9) 0.015 Uiso 1 1 calc R . . O9 O -0.4681(2) 0.16936(10) -0.03834(11) 0.0178(4) Uani 1 1 d . . . H9 H -0.615(4) 0.0988(18) -0.0454(14) 0.027 Uiso 1 1 calc R . . O10 O -0.1830(2) 0.55642(10) 0.15149(10) 0.0147(4) Uani 1 1 d . . . C11 C -0.2044(3) 0.65795(14) 0.23216(14) 0.0131(4) Uani 1 1 d . . . H11A H -0.2355(5) 0.6294(4) 0.3127(11) 0.016 Uiso 1 1 calc R . . H11B H -0.3383(18) 0.6968(5) 0.2055(4) 0.016 Uiso 1 1 calc R . . C12 C 0.0349(3) 0.74818(14) 0.23150(14) 0.0136(4) Uani 1 1 d . . . H12A H 0.0686(6) 0.7699(3) 0.1494(12) 0.016 Uiso 1 1 calc R . . H12B H 0.1648(19) 0.7083(6) 0.2609(4) 0.016 Uiso 1 1 calc R . . C13 C 0.0376(3) 0.86599(14) 0.30785(14) 0.0145(4) Uani 1 1 d . . . H13A H 0.0032(6) 0.8439(3) 0.3917(12) 0.017 Uiso 1 1 calc R . . H13B H -0.0949(19) 0.9068(6) 0.2778(4) 0.017 Uiso 1 1 calc R . . C14 C 0.2802(3) 0.95701(14) 0.30692(14) 0.0136(4) Uani 1 1 d . . . H14A H 0.4123(18) 0.9160(6) 0.3359(4) 0.016 Uiso 1 1 calc R . . H14B H 0.3135(5) 0.9797(3) 0.2235(11) 0.016 Uiso 1 1 calc R . . C15 C 0.2844(3) 1.07419(14) 0.38426(14) 0.0139(4) Uani 1 1 d . . . H15A H 0.1510(18) 1.1144(5) 0.3553(4) 0.017 Uiso 1 1 calc R . . H15B H 0.2506(5) 1.0509(3) 0.4675(11) 0.017 Uiso 1 1 calc R . . C16 C 0.5232(3) 1.16757(15) 0.38539(14) 0.0137(4) Uani 1 1 d . . . H16A H 0.6600(19) 1.1265(6) 0.4126(4) 0.016 Uiso 1 1 calc R . . H16B H 0.5551(5) 1.1940(4) 0.3014(12) 0.016 Uiso 1 1 calc R . . C17 C 0.5239(3) 1.28128(14) 0.46633(14) 0.0163(4) Uani 1 1 d . . . H17A H 0.4944(5) 1.2546(4) 0.5511(12) 0.020 Uiso 1 1 calc R . . H17B H 0.3838(19) 1.3216(6) 0.4398(4) 0.020 Uiso 1 1 calc R . . C18 C 0.7598(3) 1.37627(16) 0.46653(16) 0.0219(5) Uani 1 1 d . . . H18A H 0.8982(17) 1.3379(6) 0.4936(12) 0.033 Uiso 1 1 calc R . . H18B H 0.7489(10) 1.4480(11) 0.5220(11) 0.033 Uiso 1 1 calc R . . H18C H 0.7873(13) 1.4054(10) 0.3842(10) 0.033 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 N1 0.0104(7) 0.0085(7) 0.0189(8) 0.0013(6) -0.0012(5) -0.0027(6) C2 0.0112(8) 0.0099(8) 0.0154(8) 0.0012(6) -0.0009(6) 0.0010(6) C3 0.0098(8) 0.0073(8) 0.0131(8) 0.0011(6) -0.0005(6) 0.0010(6) C4 0.0139(8) 0.0084(7) 0.0116(7) 0.0001(6) 0.0001(6) 0.0039(6) C5 0.0102(7) 0.0104(8) 0.0143(8) -0.0007(6) 0.0018(6) 0.0006(6) C6 0.0107(8) 0.0072(8) 0.0139(8) 0.0017(6) -0.0017(6) -0.0004(6) C7 0.0127(8) 0.0100(8) 0.0158(8) 0.0000(6) 0.0012(6) 0.0032(6) C8 0.0104(8) 0.0108(8) 0.0156(8) 0.0006(6) 0.0007(6) 0.0007(6) O9 0.0152(6) 0.0116(6) 0.0248(7) -0.0080(5) 0.0066(5) -0.0011(4) O10 0.0120(6) 0.0081(6) 0.0216(7) -0.0045(5) 0.0044(4) -0.0034(4) C11 0.0151(8) 0.0065(8) 0.0168(8) -0.0029(6) 0.0011(6) 0.0005(6) C12 0.0136(8) 0.0091(8) 0.0173(8) -0.0015(7) 0.0031(6) 0.0001(6) C13 0.0150(8) 0.0092(8) 0.0183(8) -0.0006(7) 0.0031(6) -0.0004(6) C14 0.0129(8) 0.0089(8) 0.0185(9) 0.0002(7) 0.0023(6) 0.0009(6) C15 0.0141(8) 0.0083(8) 0.0186(8) 0.0004(6) 0.0032(6) 0.0003(6) C16 0.0141(8) 0.0090(8) 0.0174(8) 0.0008(6) 0.0009(6) 0.0008(6) C17 0.0200(9) 0.0089(8) 0.0188(8) 0.0002(7) 0.0017(6) -0.0004(6) C18 0.0244(9) 0.0119(8) 0.0262(10) 0.0007(7) -0.0018(7) -0.0040(7) _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 N1 C2 1.294(2) . ? N1 N1 1.392(2) 2_355 ? C2 C3 1.446(2) . ? C2 H2 1.0358 . ? C3 C8 1.398(2) . ? C3 C4 1.421(2) . ? C4 O9 1.3534(19) . ? C4 C5 1.384(2) . ? C5 C6 1.392(2) . ? C5 H5 0.9345 . ? C6 O10 1.3622(18) . ? C6 C7 1.399(2) . ? C7 C8 1.385(2) . ? C7 H7 0.9676 . ? C8 H8 0.9588 . ? O9 H9 1.0176 . ? O10 C11 1.4384(18) . ? C11 C12 1.510(2) . ? C11 H11A 0.9813 . ? C11 H11B 0.9813 . ? C12 C13 1.527(2) . ? C12 H12A 0.9790 . ? C12 H12B 0.9790 . ? C13 C14 1.529(2) . ? C13 H13A 0.9994 . ? C13 H13B 0.9994 . ? C14 C15 1.525(2) . ? C14 H14A 0.9955 . ? C14 H14B 0.9955 . ? C15 C16 1.524(2) . ? C15 H15A 0.9957 . ? C15 H15B 0.9957 . ? C16 C17 1.520(2) . ? C16 H16A 1.0113 . ? C16 H16B 1.0113 . ? C17 C18 1.522(2) . ? C17 H17A 1.0191 . ? C17 H17B 1.0191 . ? C18 H18A 1.0002 . ? C18 H18B 1.0002 . ? C18 H18C 1.0002 . ? 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 C2 N1 N1 113.76(17) . 2_355 ? N1 C2 C3 121.04(15) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C8 C3 C4 117.65(14) . . ? C8 C3 C2 120.60(14) . . ? C4 C3 C2 121.75(15) . . ? O9 C4 C5 118.11(14) . . ? O9 C4 C3 121.41(14) . . ? C5 C4 C3 120.47(15) . . ? C4 C5 C6 120.18(14) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? O10 C6 C5 114.85(14) . . ? O10 C6 C7 124.49(14) . . ? C5 C6 C7 120.65(14) . . ? C8 C7 C6 118.60(15) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C3 122.43(14) . . ? C7 C8 H8 118.8 . . ? C3 C8 H8 118.8 . . ? C4 O9 H9 109.5 . . ? C6 O10 C11 118.78(12) . . ? O10 C11 C12 106.19(12) . . ? O10 C11 H11A 110.5 . . ? C12 C11 H11A 110.5 . . ? O10 C11 H11B 110.5 . . ? C12 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C11 C12 C13 112.93(13) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 112.72(13) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 112.85(13) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 114.46(13) . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 113.07(13) . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C18 113.56(14) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 N1 N1 C2 C3 179.77(13) 2_355 . . . ? N1 C2 C3 C8 179.57(13) . . . . ? N1 C2 C3 C4 0.0(2) . . . . ? C8 C3 C4 O9 179.53(12) . . . . ? C2 C3 C4 O9 -0.9(2) . . . . ? C8 C3 C4 C5 -0.2(2) . . . . ? C2 C3 C4 C5 179.37(12) . . . . ? O9 C4 C5 C6 -178.68(12) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 O10 178.11(12) . . . . ? C4 C5 C6 C7 -1.1(2) . . . . ? O10 C6 C7 C8 -178.89(13) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C3 0.7(2) . . . . ? C4 C3 C8 C7 -0.7(2) . . . . ? C2 C3 C8 C7 179.75(13) . . . . ? C5 C6 O10 C11 -179.74(12) . . . . ? C7 C6 O10 C11 -0.6(2) . . . . ? C6 O10 C11 C12 178.58(11) . . . . ? O10 C11 C12 C13 176.65(11) . . . . ? C11 C12 C13 C14 179.98(12) . . . . ? C12 C13 C14 C15 -179.35(12) . . . . ? C13 C14 C15 C16 -179.81(12) . . . . ? C14 C15 C16 C17 -178.16(12) . . . . ? C15 C16 C17 C18 -178.98(12) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 71.12 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.349 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.088