# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _audit_creation_date 10-01-06 _publ_contact_author_name 'Laurent Douce' _publ_contact_author_address ; Groupe des Materiaux Organiques, UMR-CNRS 46 IPCMS 23, rue du Loess F-67037 STRASBOURG Cedex France ; _publ_contact_author_email LAURENT.DOUCE@IPCMS.U-STRASBG.FR _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; New ionic liquid crystal based on imidazolium salts. ; loop_ _publ_author_name _publ_author_address W.Dobbs ; Groupe des Materiaux Organiques, UMR-CNRS 46 IPCMS 23, rue du Loess F-67037 STRASBOURG Cedex France ; L.Douce ; Groupe des Materiaux Organiques, UMR-CNRS 46 IPCMS 23, rue du Loess F-67037 STRASBOURG Cedex France ; L.Allouche ; Groupe des Materiaux Organiques, UMR-CNRS 46 IPCMS 23, rue du Loess F-67037 STRASBOURG Cedex France ; A.Louati ; Service de R.M.N. Institut de Chimie de Strasbourg, CNRS-ULP 1 rue Blaise Pascal 67000 Strasbourg France ; F.Malbosc ; Ecole Nationale Superieure de Chimie de Mulhouse 3 rue Alfred Werner 68093 Mulhouse Cedex France ; R.Welter ; Laboratoire DECMET, UMR CNRS 7513 Universit\'e Louis Pasteur Strasbourg France ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Blessing, R.H. (1987). Crystallogr. Rev. 1, 3-58. Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. A.L. Spek, PLATON 98, Utrecht University, The Netherland, 1998. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. University of Gottingen. Germany. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_shelxl _database_code_depnum_ccdc_archive 'CCDC 293491' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H37 N2 O, Br' _chemical_formula_sum 'C23 H37 Br N2 O' _chemical_formula_weight 437.46 _chemical_absolute_configuration . 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' Br Br -0.2901 2.4595 '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 8.7610(2) _cell_length_b 9.7620(3) _cell_length_c 27.2570(13) _cell_angle_alpha 93.6750(13) _cell_angle_beta 96.2780(12) _cell_angle_gamma 95.237(4) _cell_volume 2301.03(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7021 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.801 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 16426 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.52 _reflns_number_total 10512 _reflns_number_gt 7277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0435P)^2^+0.6694P] 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 10512 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Br1 Br 0.21025(3) 0.50802(3) 0.095154(13) 0.03727(10) Uani 1 1 d . . . Br2 Br 0.26508(3) 0.09892(3) -0.021631(11) 0.03073(9) Uani 1 1 d . . . O1 O 0.7807(2) 0.4947(3) 0.29122(8) 0.0474(6) Uani 1 1 d . . . O4 O 0.8295(2) 1.0646(2) 0.29075(8) 0.0425(6) Uani 1 1 d . . . N2 N 0.3027(2) 1.0290(2) 0.11024(8) 0.0266(5) Uani 1 1 d . . . N6 N 0.6836(2) 0.4746(2) 0.05637(8) 0.0251(5) Uani 1 1 d . . . N8 N 0.8013(2) 0.3201(2) 0.01938(9) 0.0256(5) Uani 1 1 d . . . N9 N 0.0740(2) 1.0853(2) 0.11803(9) 0.0276(5) Uani 1 1 d . . . C1 C 0.2149(3) 1.1325(3) 0.10952(11) 0.0271(6) Uani 1 1 d . . . H1 H 0.2474 1.2251 0.1039 0.033 Uiso 1 1 calc . . . C2 C 0.0716(3) 0.9465(3) 0.12345(12) 0.0365(8) Uani 1 1 d . . . H2 H -0.0150 0.8864 0.1293 0.044 Uiso 1 1 calc . . . C3 C 0.2146(3) 0.9110(3) 0.11889(12) 0.0337(7) Uani 1 1 d . . . H3 H 0.2482 0.8215 0.1212 0.040 Uiso 1 1 calc . . . C4 C -0.0566(3) 1.1682(3) 0.12182(12) 0.0375(8) Uani 1 1 d . . . H4A H -0.0256 1.2636 0.1152 0.056 Uiso 1 1 calc . . . H4B H -0.0879 1.1661 0.1552 0.056 Uiso 1 1 calc . . . H4C H -0.1433 1.1301 0.0975 0.056 Uiso 1 1 calc . . . C5 C 0.4698(3) 1.0399(3) 0.10402(11) 0.0317(7) Uani 1 1 d . . . H5A H 0.4970 1.1248 0.0876 0.038 Uiso 1 1 calc . . . H5B H 0.4913 0.9600 0.0825 0.038 Uiso 1 1 calc . . . C6 C 0.5678(3) 1.0435(3) 0.15321(11) 0.0276(7) Uani 1 1 d . . . C7 C 0.5912(3) 1.1618(3) 0.18495(12) 0.0347(7) Uani 1 1 d . . . H7 H 0.5456 1.2420 0.1753 0.042 Uiso 1 1 calc . . . C8 C 0.6791(3) 1.1659(3) 0.23022(12) 0.0349(7) Uani 1 1 d . . . H8 H 0.6937 1.2481 0.2515 0.042 Uiso 1 1 calc . . . C9 C 0.7464(3) 1.0486(3) 0.24464(11) 0.0327(7) Uani 1 1 d . . . C10 C 0.7260(3) 0.9297(3) 0.21326(12) 0.0364(7) Uani 1 1 d . . . H10 H 0.7727 0.8499 0.2227 0.044 Uiso 1 1 calc . . . C11 C 0.6371(3) 0.9278(3) 0.16791(12) 0.0335(7) Uani 1 1 d . . . H11 H 0.6231 0.8459 0.1465 0.040 Uiso 1 1 calc . . . C12 C 0.9023(4) 0.9502(4) 0.30974(13) 0.0457(9) Uani 1 1 d . . . H12A H 0.9805 0.9219 0.2885 0.055 Uiso 1 1 calc . . . H12B H 0.8251 0.8704 0.3114 0.055 Uiso 1 1 calc . . . C13 C 0.9773(3) 1.0018(4) 0.36090(12) 0.0439(9) Uani 1 1 d . . . H13A H 0.8965 1.0317 0.3808 0.053 Uiso 1 1 calc . . . H13B H 1.0503 1.0837 0.3581 0.053 Uiso 1 1 calc . . . C14 C 1.0638(4) 0.8963(4) 0.38854(14) 0.0562(10) Uani 1 1 d . . . H14A H 1.1450 0.8659 0.3690 0.067 Uiso 1 1 calc . . . H14B H 0.9913 0.8145 0.3920 0.067 Uiso 1 1 calc . . . C15 C 1.1383(4) 0.9545(4) 0.44000(12) 0.0468(9) Uani 1 1 d . . . H15A H 1.2122 1.0350 0.4361 0.056 Uiso 1 1 calc . . . H15B H 1.0568 0.9881 0.4588 0.056 Uiso 1 1 calc . . . C16 C 1.2225(4) 0.8533(4) 0.47022(15) 0.0634(12) Uani 1 1 d . . . H16A H 1.1486 0.7734 0.4747 0.076 Uiso 1 1 calc . . . H16B H 1.3035 0.8189 0.4514 0.076 Uiso 1 1 calc . . . C17 C 1.2967(4) 0.9140(4) 0.52069(13) 0.0467(9) Uani 1 1 d . . . H17A H 1.3724 0.9924 0.5160 0.056 Uiso 1 1 calc . . . H17B H 1.2159 0.9511 0.5389 0.056 Uiso 1 1 calc . . . C18 C 1.3780(5) 0.8145(4) 0.55232(15) 0.0636(12) Uani 1 1 d . . . H18A H 1.3016 0.7375 0.5578 0.076 Uiso 1 1 calc . . . H18B H 1.4566 0.7752 0.5337 0.076 Uiso 1 1 calc . . . C19 C 1.4559(4) 0.8760(4) 0.60203(12) 0.0444(9) Uani 1 1 d . . . H19A H 1.3775 0.9156 0.6207 0.053 Uiso 1 1 calc . . . H19B H 1.5329 0.9526 0.5966 0.053 Uiso 1 1 calc . . . C20 C 1.5363(5) 0.7748(4) 0.63345(15) 0.0645(12) Uani 1 1 d . . . H20A H 1.4579 0.7017 0.6408 0.077 Uiso 1 1 calc . . . H20B H 1.6091 0.7302 0.6137 0.077 Uiso 1 1 calc . . . C21 C 1.6237(3) 0.8362(4) 0.68157(12) 0.0409(8) Uani 1 1 d . . . H21A H 1.5518 0.8826 0.7011 0.049 Uiso 1 1 calc . . . H21B H 1.7044 0.9075 0.6744 0.049 Uiso 1 1 calc . . . C22 C 1.6993(5) 0.7322(4) 0.71257(15) 0.0653(12) Uani 1 1 d . . . H22A H 1.6177 0.6642 0.7213 0.078 Uiso 1 1 calc . . . H22B H 1.7660 0.6819 0.6922 0.078 Uiso 1 1 calc . . . C23 C 1.7953(4) 0.7930(4) 0.75967(14) 0.0592(11) Uani 1 1 d . . . H23A H 1.8770 0.8603 0.7516 0.089 Uiso 1 1 calc . . . H23B H 1.8418 0.7192 0.7769 0.089 Uiso 1 1 calc . . . H23C H 1.7295 0.8389 0.7811 0.089 Uiso 1 1 calc . . . C24 C 0.8193(3) 0.4423(3) 0.04412(11) 0.0268(6) Uani 1 1 d . . . H24 H 0.9143 0.4984 0.0519 0.032 Uiso 1 1 calc . . . C25 C 0.5736(3) 0.3685(3) 0.03781(11) 0.0279(6) Uani 1 1 d . . . H25 H 0.4663 0.3641 0.0409 0.033 Uiso 1 1 calc . . . C26 C 0.6470(3) 0.2719(3) 0.01442(11) 0.0269(6) Uani 1 1 d . . . H26 H 0.6010 0.1872 -0.0022 0.032 Uiso 1 1 calc . . . C27 C 0.9252(3) 0.2506(3) -0.00098(12) 0.0340(7) Uani 1 1 d . . . H27A H 0.9249 0.2670 -0.0361 0.051 Uiso 1 1 calc . . . H27B H 0.9084 0.1512 0.0025 0.051 Uiso 1 1 calc . . . H27C H 1.0250 0.2873 0.0171 0.051 Uiso 1 1 calc . . . C28 C 0.6606(3) 0.5961(3) 0.08879(11) 0.0298(7) Uani 1 1 d . . . H28A H 0.5520 0.6169 0.0827 0.036 Uiso 1 1 calc . . . H28B H 0.7273 0.6768 0.0806 0.036 Uiso 1 1 calc . . . C29 C 0.6983(3) 0.5725(3) 0.14278(11) 0.0287(7) Uani 1 1 d . . . C30 C 0.8493(3) 0.5740(3) 0.16457(12) 0.0358(7) Uani 1 1 d . . . H30 H 0.9315 0.5918 0.1451 0.043 Uiso 1 1 calc . . . C31 C 0.8829(3) 0.5504(4) 0.21392(12) 0.0416(8) Uani 1 1 d . . . H31 H 0.9871 0.5517 0.2281 0.050 Uiso 1 1 calc . . . C32 C 0.7637(3) 0.5249(3) 0.24251(11) 0.0358(7) Uani 1 1 d . . . C33 C 0.6119(3) 0.5262(3) 0.22169(12) 0.0354(7) Uani 1 1 d . . . H33 H 0.5298 0.5112 0.2414 0.042 Uiso 1 1 calc . . . C34 C 0.5808(3) 0.5493(3) 0.17246(11) 0.0307(7) Uani 1 1 d . . . H34 H 0.4766 0.5494 0.1585 0.037 Uiso 1 1 calc . . . C35 C 0.9327(4) 0.4886(5) 0.31531(13) 0.0662(13) Uani 1 1 d . . . H35A H 0.9882 0.5823 0.3204 0.079 Uiso 1 1 calc . . . H35B H 0.9910 0.4302 0.2946 0.079 Uiso 1 1 calc . . . C36 C 0.9208(4) 0.4291(5) 0.36426(13) 0.0620(12) Uani 1 1 d . . . H36A H 0.8842 0.3298 0.3586 0.074 Uiso 1 1 calc . . . H36B H 0.8438 0.4754 0.3816 0.074 Uiso 1 1 calc . . . C37 C 1.0744(5) 0.4462(6) 0.39673(14) 0.0864(17) Uani 1 1 d . . . H37A H 1.1060 0.5459 0.4045 0.104 Uiso 1 1 calc . . . H37B H 1.1532 0.4079 0.3779 0.104 Uiso 1 1 calc . . . C38 C 1.0721(5) 0.3763(5) 0.44508(14) 0.0695(13) Uani 1 1 d . . . H38A H 1.0499 0.2755 0.4375 0.083 Uiso 1 1 calc . . . H38B H 0.9875 0.4086 0.4627 0.083 Uiso 1 1 calc . . . C39 C 1.2238(5) 0.4053(6) 0.47902(15) 0.0910(18) Uani 1 1 d . . . H39A H 1.3088 0.3779 0.4606 0.109 Uiso 1 1 calc . . . H39B H 1.2429 0.5058 0.4879 0.109 Uiso 1 1 calc . . . C40 C 1.2274(5) 0.3313(5) 0.52602(14) 0.0656(12) Uani 1 1 d . . . H40A H 1.2130 0.2306 0.5173 0.079 Uiso 1 1 calc . . . H40B H 1.1400 0.3557 0.5439 0.079 Uiso 1 1 calc . . . C41 C 1.3773(4) 0.3659(6) 0.56054(14) 0.0812(16) Uani 1 1 d . . . H41A H 1.4648 0.3447 0.5422 0.097 Uiso 1 1 calc . . . H41B H 1.3897 0.4663 0.5700 0.097 Uiso 1 1 calc . . . C42 C 1.3864(4) 0.2896(4) 0.60731(13) 0.0578(11) Uani 1 1 d . . . H42A H 1.2983 0.3096 0.6256 0.069 Uiso 1 1 calc . . . H42B H 1.3761 0.1892 0.5980 0.069 Uiso 1 1 calc . . . C43 C 1.5350(4) 0.3270(5) 0.64143(14) 0.0754(15) Uani 1 1 d . . . H43A H 1.6229 0.3112 0.6226 0.090 Uiso 1 1 calc . . . H43B H 1.5428 0.4268 0.6517 0.090 Uiso 1 1 calc . . . C44 C 1.5504(4) 0.2480(4) 0.68734(13) 0.0514(9) Uani 1 1 d . . . H44A H 1.5422 0.1481 0.6772 0.062 Uiso 1 1 calc . . . H44B H 1.4634 0.2645 0.7066 0.062 Uiso 1 1 calc . . . C45 C 1.7003(4) 0.2867(5) 0.72045(14) 0.0644(13) Uani 1 1 d . . . H45A H 1.7870 0.2675 0.7015 0.077 Uiso 1 1 calc . . . H45B H 1.7099 0.3872 0.7296 0.077 Uiso 1 1 calc . . . C46 C 1.7151(4) 0.2120(4) 0.76712(14) 0.0586(11) Uani 1 1 d . . . H46A H 1.6357 0.2372 0.7878 0.088 Uiso 1 1 calc . . . H46B H 1.8175 0.2379 0.7854 0.088 Uiso 1 1 calc . . . H46C H 1.7018 0.1122 0.7586 0.088 Uiso 1 1 calc . . . 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 Br1 0.02600(15) 0.03462(19) 0.0492(2) 0.00464(15) -0.00481(13) 0.00215(12) Br2 0.02686(15) 0.03074(17) 0.03475(19) 0.00484(13) 0.00371(12) 0.00184(11) O1 0.0497(13) 0.0712(17) 0.0234(13) 0.0051(12) -0.0039(10) 0.0262(12) O4 0.0454(12) 0.0520(15) 0.0292(13) 0.0033(11) -0.0083(10) 0.0150(11) N2 0.0276(12) 0.0310(14) 0.0204(13) 0.0035(11) -0.0031(10) 0.0048(10) N6 0.0268(12) 0.0272(13) 0.0205(13) 0.0031(11) -0.0010(9) 0.0025(10) N8 0.0249(11) 0.0281(13) 0.0232(14) 0.0029(11) 0.0009(10) 0.0014(10) N9 0.0247(11) 0.0299(14) 0.0274(14) 0.0037(11) -0.0008(10) 0.0014(10) C1 0.0302(14) 0.0287(16) 0.0228(16) 0.0065(13) 0.0008(12) 0.0042(12) C2 0.0331(16) 0.0331(18) 0.040(2) 0.0073(15) -0.0037(14) -0.0057(13) C3 0.0410(17) 0.0253(16) 0.0318(19) 0.0042(14) -0.0085(13) 0.0008(13) C4 0.0276(15) 0.046(2) 0.040(2) 0.0040(16) 0.0044(13) 0.0080(13) C5 0.0311(15) 0.0414(18) 0.0245(17) 0.0071(14) 0.0031(12) 0.0111(13) C6 0.0220(13) 0.0354(17) 0.0272(17) 0.0063(14) 0.0052(12) 0.0071(12) C7 0.0361(16) 0.0362(18) 0.0337(19) 0.0080(15) 0.0016(13) 0.0138(13) C8 0.0370(16) 0.0329(18) 0.0335(19) -0.0020(15) -0.0026(13) 0.0079(13) C9 0.0273(14) 0.045(2) 0.0261(18) 0.0088(15) 0.0002(12) 0.0038(13) C10 0.0399(17) 0.0338(18) 0.036(2) 0.0076(15) -0.0039(14) 0.0110(14) C11 0.0380(16) 0.0301(17) 0.0307(19) 0.0012(14) -0.0039(13) 0.0047(13) C12 0.0420(18) 0.056(2) 0.038(2) 0.0164(18) -0.0091(15) 0.0045(16) C13 0.0352(16) 0.068(2) 0.030(2) 0.0126(18) 0.0003(14) 0.0106(16) C14 0.060(2) 0.059(3) 0.045(2) 0.018(2) -0.0171(18) -0.0026(18) C15 0.0380(17) 0.073(3) 0.031(2) 0.0142(19) -0.0004(14) 0.0121(17) C16 0.066(2) 0.064(3) 0.052(3) 0.020(2) -0.031(2) -0.006(2) C17 0.0372(17) 0.071(3) 0.034(2) 0.0162(19) -0.0006(14) 0.0092(16) C18 0.074(3) 0.059(3) 0.050(3) 0.017(2) -0.030(2) -0.001(2) C19 0.0375(17) 0.065(2) 0.031(2) 0.0103(18) -0.0039(14) 0.0085(16) C20 0.082(3) 0.056(3) 0.047(3) 0.012(2) -0.033(2) 0.004(2) C21 0.0360(16) 0.055(2) 0.032(2) 0.0080(17) -0.0014(14) 0.0077(15) C22 0.087(3) 0.053(2) 0.047(3) 0.005(2) -0.033(2) 0.011(2) C23 0.057(2) 0.080(3) 0.038(2) 0.005(2) -0.0112(18) 0.015(2) C24 0.0293(14) 0.0265(16) 0.0234(16) 0.0053(13) -0.0014(12) -0.0004(12) C25 0.0246(13) 0.0315(16) 0.0262(17) 0.0061(13) -0.0016(12) -0.0018(12) C26 0.0283(14) 0.0253(15) 0.0249(17) 0.0014(13) -0.0011(12) -0.0037(11) C27 0.0342(15) 0.0368(18) 0.0327(19) 0.0007(15) 0.0092(13) 0.0073(13) C28 0.0397(16) 0.0252(16) 0.0244(17) 0.0009(13) -0.0003(13) 0.0074(12) C29 0.0356(15) 0.0232(15) 0.0271(17) 0.0013(13) -0.0020(12) 0.0083(12) C30 0.0328(15) 0.044(2) 0.0300(19) 0.0014(15) 0.0011(13) 0.0077(14) C31 0.0319(16) 0.059(2) 0.034(2) 0.0000(17) -0.0059(14) 0.0136(15) C32 0.0445(17) 0.0394(19) 0.0238(18) -0.0001(15) -0.0030(13) 0.0153(14) C33 0.0350(16) 0.0412(19) 0.0318(19) 0.0034(15) 0.0034(13) 0.0134(14) C34 0.0312(15) 0.0315(17) 0.0284(18) 0.0005(14) -0.0044(12) 0.0090(12) C35 0.051(2) 0.127(4) 0.024(2) 0.010(2) -0.0056(16) 0.041(2) C36 0.070(2) 0.094(3) 0.026(2) 0.003(2) -0.0066(17) 0.044(2) C37 0.066(3) 0.178(5) 0.024(2) 0.017(3) 0.0006(19) 0.059(3) C38 0.087(3) 0.100(3) 0.026(2) 0.001(2) -0.0097(19) 0.055(3) C39 0.066(3) 0.191(6) 0.027(2) 0.024(3) 0.0008(19) 0.065(3) C40 0.084(3) 0.085(3) 0.029(2) -0.004(2) -0.0151(19) 0.046(2) C41 0.056(2) 0.166(5) 0.029(2) 0.020(3) 0.0004(18) 0.052(3) C42 0.074(3) 0.072(3) 0.029(2) -0.0003(19) -0.0127(17) 0.039(2) C43 0.055(2) 0.145(5) 0.033(2) 0.025(3) 0.0012(18) 0.039(3) C44 0.066(2) 0.057(2) 0.031(2) -0.0011(18) -0.0105(16) 0.0292(19) C45 0.042(2) 0.119(4) 0.038(2) 0.022(2) 0.0014(16) 0.029(2) C46 0.065(2) 0.069(3) 0.040(2) 0.011(2) -0.0110(18) 0.016(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 O1 C32 1.374(3) . ? O1 C35 1.427(4) . ? O4 C9 1.374(4) . ? O4 C12 1.433(4) . ? N2 C1 1.324(3) . ? N2 C3 1.375(4) . ? N2 C5 1.487(3) . ? N6 C24 1.329(3) . ? N6 C25 1.379(4) . ? N6 C28 1.475(4) . ? N8 C24 1.320(4) . ? N8 C26 1.380(3) . ? N8 C27 1.471(3) . ? N9 C1 1.328(3) . ? N9 C2 1.371(4) . ? N9 C4 1.469(3) . ? C1 H1 0.9500 . ? C2 C3 1.347(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.508(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.384(4) . ? C6 C11 1.391(4) . ? C7 C8 1.378(4) . ? C7 H7 0.9500 . ? C8 C9 1.394(4) . ? C8 H8 0.9500 . ? C9 C10 1.383(5) . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.510(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.523(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.532(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.518(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.515(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.510(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.520(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.504(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.515(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.511(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24 0.9500 . ? C25 C26 1.354(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.509(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.388(4) . ? C29 C34 1.389(4) . ? C30 C31 1.384(4) . ? C30 H30 0.9500 . ? C31 C32 1.384(4) . ? C31 H31 0.9500 . ? C32 C33 1.389(4) . ? C33 C34 1.377(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.499(5) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.517(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.524(5) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.527(6) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.509(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.527(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.516(5) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.516(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.512(5) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.513(5) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.506(5) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? 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 C32 O1 C35 118.6(3) . . ? C9 O4 C12 119.2(3) . . ? C1 N2 C3 108.7(2) . . ? C1 N2 C5 125.5(2) . . ? C3 N2 C5 125.8(2) . . ? C24 N6 C25 108.0(2) . . ? C24 N6 C28 124.9(2) . . ? C25 N6 C28 126.7(2) . . ? C24 N8 C26 108.5(2) . . ? C24 N8 C27 125.2(2) . . ? C26 N8 C27 126.2(2) . . ? C1 N9 C2 108.4(2) . . ? C1 N9 C4 125.8(2) . . ? C2 N9 C4 125.8(2) . . ? N2 C1 N9 108.6(2) . . ? N2 C1 H1 125.7 . . ? N9 C1 H1 125.7 . . ? C3 C2 N9 107.4(2) . . ? C3 C2 H2 126.3 . . ? N9 C2 H2 126.3 . . ? C2 C3 N2 106.8(2) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N9 C4 H4A 109.5 . . ? N9 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N9 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 111.3(2) . . ? N2 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C11 118.2(3) . . ? C7 C6 C5 120.9(2) . . ? C11 C6 C5 120.8(3) . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? O4 C9 C10 125.8(3) . . ? O4 C9 C8 114.3(3) . . ? C10 C9 C8 119.9(3) . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C6 121.2(3) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? O4 C12 C13 105.1(3) . . ? O4 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? O4 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C12 C13 C14 114.6(3) . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 112.3(3) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 115.0(3) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 113.9(4) . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C15 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 115.2(3) . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? C16 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C17 115.2(4) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 114.6(3) . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 115.3(3) . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20B 108.4 . . ? C19 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C20 C21 C22 114.0(3) . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 114.9(3) . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N8 C24 N6 109.4(2) . . ? N8 C24 H24 125.3 . . ? N6 C24 H24 125.3 . . ? C26 C25 N6 107.2(2) . . ? C26 C25 H25 126.4 . . ? N6 C25 H25 126.4 . . ? C25 C26 N8 106.8(3) . . ? C25 C26 H26 126.6 . . ? N8 C26 H26 126.6 . . ? N8 C27 H27A 109.5 . . ? N8 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N8 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N6 C28 C29 111.7(2) . . ? N6 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? N6 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C34 117.8(3) . . ? C30 C29 C28 121.9(3) . . ? C34 C29 C28 120.3(2) . . ? C31 C30 C29 121.6(3) . . ? C31 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C30 C31 C32 119.5(3) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? O1 C32 C31 125.4(3) . . ? O1 C32 C33 114.8(3) . . ? C31 C32 C33 119.7(3) . . ? C34 C33 C32 119.9(3) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C29 121.4(3) . . ? C33 C34 H34 119.3 . . ? C29 C34 H34 119.3 . . ? O1 C35 C36 108.7(3) . . ? O1 C35 H35A 110.0 . . ? C36 C35 H35A 110.0 . . ? O1 C35 H35B 110.0 . . ? C36 C35 H35B 110.0 . . ? H35A C35 H35B 108.3 . . ? C35 C36 C37 111.9(4) . . ? C35 C36 H36A 109.2 . . ? C37 C36 H36A 109.2 . . ? C35 C36 H36B 109.2 . . ? C37 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? C36 C37 C38 114.0(4) . . ? C36 C37 H37A 108.7 . . ? C38 C37 H37A 108.7 . . ? C36 C37 H37B 108.7 . . ? C38 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C37 C38 C39 113.0(4) . . ? C37 C38 H38A 109.0 . . ? C39 C38 H38A 109.0 . . ? C37 C38 H38B 109.0 . . ? C39 C38 H38B 109.0 . . ? H38A C38 H38B 107.8 . . ? C40 C39 C38 114.1(4) . . ? C40 C39 H39A 108.7 . . ? C38 C39 H39A 108.7 . . ? C40 C39 H39B 108.7 . . ? C38 C39 H39B 108.7 . . ? H39A C39 H39B 107.6 . . ? C39 C40 C41 113.4(4) . . ? C39 C40 H40A 108.9 . . ? C41 C40 H40A 108.9 . . ? C39 C40 H40B 108.9 . . ? C41 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? C42 C41 C40 114.6(4) . . ? C42 C41 H41A 108.6 . . ? C40 C41 H41A 108.6 . . ? C42 C41 H41B 108.6 . . ? C40 C41 H41B 108.6 . . ? H41A C41 H41B 107.6 . . ? C43 C42 C41 113.8(4) . . ? C43 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? C43 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? C44 C43 C42 115.0(4) . . ? C44 C43 H43A 108.5 . . ? C42 C43 H43A 108.5 . . ? C44 C43 H43B 108.5 . . ? C42 C43 H43B 108.5 . . ? H43A C43 H43B 107.5 . . ? C43 C44 C45 113.8(4) . . ? C43 C44 H44A 108.8 . . ? C45 C44 H44A 108.8 . . ? C43 C44 H44B 108.8 . . ? C45 C44 H44B 108.8 . . ? H44A C44 H44B 107.7 . . ? C46 C45 C44 114.4(3) . . ? C46 C45 H45A 108.7 . . ? C44 C45 H45A 108.7 . . ? C46 C45 H45B 108.7 . . ? C44 C45 H45B 108.7 . . ? H45A C45 H45B 107.6 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.541 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.080