# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global #============================================================================== # 1. SUBMISSION DETAILS _journal_coden_Cambridge 1145 _publ_contact_author_name 'Rudolf Zentel' _publ_contact_author_address # Name and address of author for correspondence ; Institut of Organic Chemistry University of Mainz Duesbergweg 10-14 55099 Mainz, Germany ; _publ_contact_author_phone '+49 6131 3925873' _publ_contact_author_fax '+49 6131 3924778' _publ_contact_author_email zentel@.uni-mainz.de _journal_name_full 'Journal of Material Chemistry' loop_ _publ_author_name _publ_author_address 'Deindorfer, Pia' ; Institut fur Organische Chemie Universitat Mainz Duesbergweg 10-14 55099 Mainz, Germay ; 'Geiger, Thomas' ; EMPA Laboratory for Functional Polymers Uberlandstr. 129 8600 Dubendorf, Switzerland ; 'Schollmeyer, Dieter' ; Institut fur Organische Chemie Universitat Mainz Duesbergweg 10-14 55099 Mainz, Germay ; 'Ye, Jian Hui' ; Institut fur Organische Chemie Universitat Mainz Duesbergweg 10-14 55099 Mainz, Germay ; 'Zentel, Rudolf' ; Institut fur Organische Chemie Universitat Mainz Duesbergweg 10-14 55099 Mainz, Germay ; _publ_section_title ; Semicarbazides as gel forming agents for common solvents and liquid crystals ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. J. Appl. Cryst. 27. 435-436. Drager, M. & Gattow G. (1971). Acta Chem. Scand. 25, 761-762. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Sheldrick, G. M. (1997). SHELXL97. Program for Crystal Structure Refinement. University of Gottingen, Germany. ; data_geig2 _database_code_depnum_CCDC_archive 151383 _audit_creation_method SHELXL-97 _database_code_csd XAYSUL _chemical_name_systematic ; ethyl2-[(octylamino)carbonyl]hydrazinecarboxylate ; _chemical_name_common octylsemicarbazid _chemical_formula_moiety 'C12 H25 N3 O3' _chemical_formula_sum 'C12 H25 N3 O3' _chemical_formula_weight 259.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 36.062(2) _cell_length_b 9.1053(3) _cell_length_c 4.6794(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1536.51(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40 _cell_measurement_theta_max 50 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf Nonius' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3185 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 74.83 _reflns_number_total 3126 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius Software V5.0' _computing_cell_refinement 'Enraf Nonius Software V5.0' _computing_data_reduction 'CORINC (Dager, 1971)' _computing_structure_solution 'SIR-92 (Altomare, 1994)' _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^)+(0.0754P)^2^+0.2093P] 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 refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(3) _refine_ls_number_reflns 3126 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.04205(12) 0.3376(6) 0.6003(16) 0.139(2) Uani 1 d . . . H1A H -0.0561 0.3206 0.7715 0.30(3) Uiso 1 calc R . . H1B H -0.0490 0.2669 0.4579 0.30(3) Uiso 1 calc R . . H1C H -0.0470 0.4348 0.5306 0.30(3) Uiso 1 calc R . . C2 C -0.00197(14) 0.3230(6) 0.6636(17) 0.142(2) Uani 1 d . . . H2A H 0.0110 0.3999 0.5605 0.23(3) Uiso 1 calc R . . H2B H 0.0015 0.3420 0.8658 0.23(3) Uiso 1 calc R . . C3 C 0.01541(11) 0.1899(5) 0.6001(15) 0.1197(16) Uani 1 d . . . H3A H 0.0117 0.1701 0.3985 0.25(3) Uiso 1 calc R . . H3B H 0.0028 0.1131 0.7056 0.25(3) Uiso 1 calc R . . C4 C 0.05650(11) 0.1772(5) 0.6619(12) 0.1094(14) Uani 1 d . . . H4A H 0.0693 0.2539 0.5572 0.117(11) Uiso 1 calc R . . H4B H 0.0604 0.1955 0.8639 0.117(11) Uiso 1 calc R . . C5 C 0.07390(9) 0.0336(5) 0.5884(12) 0.1009(12) Uani 1 d . . . H5A H 0.0718 0.0192 0.3836 0.27(3) Uiso 1 calc R . . H5B H 0.0598 -0.0438 0.6803 0.27(3) Uiso 1 calc R . . C6 C 0.11373(8) 0.0161(3) 0.6704(10) 0.0812(9) Uani 1 d . . . H6A H 0.1159 0.0313 0.8749 0.097(8) Uiso 1 calc R . . H6B H 0.1279 0.0928 0.5769 0.097(8) Uiso 1 calc R . . C7 C 0.13100(8) -0.1294(3) 0.5982(8) 0.0728(8) Uani 1 d . . . H7A H 0.1157 -0.2069 0.6776 0.088(7) Uiso 1 calc R . . H7B H 0.1310 -0.1410 0.3921 0.088(7) Uiso 1 calc R . . C8 C 0.16989(7) -0.1487(2) 0.7053(6) 0.0557(6) Uani 1 d . . . H8A H 0.1698 -0.1423 0.9123 0.066(6) Uiso 1 calc R . . H8B H 0.1786 -0.2460 0.6535 0.066(6) Uiso 1 calc R . . N9 N 0.19535(5) -0.0406(2) 0.5923(4) 0.0480(4) Uani 1 d . . . H9 H 0.19530(5) 0.045(3) 0.671(3) 0.056(7) Uiso 1 d R . . C10 C 0.21915(6) -0.0715(2) 0.3833(5) 0.0405(4) Uani 1 d . . . N11 N 0.24072(5) 0.04245(17) 0.2856(5) 0.0475(4) Uani 1 d . . . H11 H 0.2529(5) 0.0400(2) 0.138(6) 0.049(7) Uiso 1 d R . . N12 N 0.23163(5) 0.18648(18) 0.3520(4) 0.0479(5) Uani 1 d . . . H12 H 0.2437(4) 0.2211(11) 0.507(5) 0.056(7) Uiso 1 d R . . C13 C 0.20609(6) 0.2574(2) 0.1930(5) 0.0448(5) Uani 1 d . . . O14 O 0.20296(5) 0.39634(16) 0.2887(4) 0.0557(4) Uani 1 d . . . C15 C 0.17635(8) 0.4864(3) 0.1381(7) 0.0678(7) Uani 1 d . . . H15A H 0.1774 0.4639 -0.0644 0.076(7) Uiso 1 calc R . . H15B H 0.1828 0.5891 0.1624 0.076(7) Uiso 1 calc R . . C16 C 0.13799(10) 0.4610(4) 0.2450(12) 0.1045(14) Uani 1 d . . . H16A H 0.1377 0.4697 0.4494 0.153(11) Uiso 1 calc R . . H16B H 0.1300 0.3644 0.1911 0.153(11) Uiso 1 calc R . . H16C H 0.1216 0.5327 0.1633 0.153(11) Uiso 1 calc R . . O18 O 0.18860(5) 0.20633(18) -0.0015(4) 0.0580(5) Uani 1 d . . . O17 O 0.22345(4) -0.19519(15) 0.2828(4) 0.0533(4) Uani 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 C1 0.080(2) 0.134(4) 0.203(6) 0.016(4) 0.007(4) 0.023(2) C2 0.097(3) 0.130(4) 0.200(7) -0.004(4) -0.002(4) 0.035(3) C3 0.081(2) 0.106(3) 0.172(5) 0.014(3) 0.004(3) 0.013(2) C4 0.081(2) 0.103(3) 0.145(4) 0.005(3) 0.003(3) 0.0242(19) C5 0.0623(17) 0.106(3) 0.134(3) 0.007(3) -0.001(2) 0.0114(17) C6 0.0600(15) 0.0783(18) 0.105(3) 0.0003(19) 0.0008(17) -0.0006(14) C7 0.0611(14) 0.0705(17) 0.087(2) 0.0030(16) 0.0034(15) -0.0083(13) C8 0.0620(13) 0.0476(11) 0.0576(14) 0.0009(10) 0.0069(11) -0.0013(10) N9 0.0544(10) 0.0362(9) 0.0533(10) -0.0109(9) 0.0081(8) -0.0008(7) C10 0.0429(10) 0.0384(10) 0.0403(10) -0.0090(9) -0.0043(8) 0.0041(8) N11 0.0503(9) 0.0405(9) 0.0518(11) -0.0116(9) 0.0073(9) -0.0015(7) N12 0.0568(10) 0.0383(8) 0.0487(11) -0.0116(8) -0.0050(9) -0.0044(7) C13 0.0518(11) 0.0382(10) 0.0445(11) -0.0095(9) 0.0053(10) -0.0058(9) O14 0.0709(10) 0.0354(7) 0.0608(10) -0.0084(7) -0.0066(9) -0.0006(6) C15 0.0828(18) 0.0419(12) 0.079(2) -0.0036(13) -0.0129(16) 0.0074(11) C16 0.075(2) 0.094(2) 0.144(4) -0.013(3) -0.002(2) 0.0163(17) O18 0.0627(10) 0.0537(9) 0.0576(10) -0.0199(8) -0.0076(8) -0.0017(7) O17 0.0638(9) 0.0378(7) 0.0583(10) -0.0169(7) 0.0044(8) 0.0055(6) _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 C1 C2 1.482(7) . ? C2 C3 1.396(6) . ? C3 C4 1.514(6) . ? C4 C5 1.491(6) . ? C5 C6 1.495(4) . ? C6 C7 1.502(4) . ? C7 C8 1.500(4) . ? C8 N9 1.447(3) . ? N9 C10 1.331(3) . ? C10 O17 1.230(2) . ? C10 N11 1.375(3) . ? N11 N12 1.387(2) . ? N12 C13 1.349(3) . ? C13 O18 1.201(3) . ? C13 O14 1.347(2) . ? O14 C15 1.446(3) . ? C15 C16 1.489(5) . ? 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 C3 C2 C1 118.2(5) . . ? C2 C3 C4 117.7(5) . . ? C5 C4 C3 115.8(4) . . ? C4 C5 C6 116.0(4) . . ? C5 C6 C7 115.8(3) . . ? C8 C7 C6 114.6(3) . . ? N9 C8 C7 113.0(2) . . ? C10 N9 C8 122.26(19) . . ? O17 C10 N9 123.8(2) . . ? O17 C10 N11 119.51(19) . . ? N9 C10 N11 116.68(18) . . ? C10 N11 N12 120.36(19) . . ? C13 N12 N11 119.38(18) . . ? O18 C13 O14 124.9(2) . . ? O18 C13 N12 126.2(2) . . ? O14 C13 N12 108.87(18) . . ? C13 O14 C15 115.21(19) . . ? O14 C15 C16 111.4(3) . . ? 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 C1 C2 C3 C4 179.1(6) . . . . ? C2 C3 C4 C5 -179.5(6) . . . . ? C3 C4 C5 C6 -175.3(5) . . . . ? C4 C5 C6 C7 179.4(4) . . . . ? C5 C6 C7 C8 -174.9(3) . . . . ? C6 C7 C8 N9 -60.1(4) . . . . ? C7 C8 N9 C10 -102.9(3) . . . . ? C8 N9 C10 O17 -5.3(3) . . . . ? C8 N9 C10 N11 177.1(2) . . . . ? O17 C10 N11 N12 167.1(2) . . . . ? N9 C10 N11 N12 -15.2(3) . . . . ? C10 N11 N12 C13 -83.2(3) . . . . ? N11 N12 C13 O18 3.0(3) . . . . ? N11 N12 C13 O14 -177.46(19) . . . . ? O18 C13 O14 C15 -0.3(3) . . . . ? N12 C13 O14 C15 -179.9(2) . . . . ? C13 O14 C15 C16 82.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.83 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max .253 _refine_diff_density_min -.127 _refine_diff_density_rms .035