Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method 'maXus' _journal_coden_Cambridge 182 loop_ _publ_author_name 'Kato, Takashi' 'Hiyama, Tamejiro' 'Ikeda, Tomiki' 'Kanie, Kiyoshi' 'Mamiya, Jun-ichi' _publ_contact_author_name 'Prof. Takashi Kato' _publ_contact_author_address ; Department of Chemistry and Biotechnology School of Engineering The University of Tokyo Hongo, Bunkyo-ku Tokyo 113-8656 Japan. ; _publ_contact_author_email 'kato@chiral.t.u-tokyo.ac.jp' _publ_contact_author_fax '+81-3-5841-8661' _publ_contact_author_phone '+81-3-5841-7440' _publ_section_title ; A mesogenic organogelator: fibrous aggregation of azobenzene derivatives with a syn-chiral carbonate moiety ; _publ_section_abstract ; A chiral azobenzene derivative containing a cyclic syn-carbonate moiety functions as a gelator for various organic solvents; the dipole-dipole interaction drives the fibrous self-assembly of the mesogenic gelator. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ; data_compound _database_code_CSD 186620 _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Orange' _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'refxyz' # Submission details _publ_requested_journal 'Chemical Communications' _diffrn_measurement_device 'DIP Image plate' _computing_data_collection 'DIP Image plate' _computing_data_reduction 'maXus (Mackay et al., 1999)' _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 50 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 396.487 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C23 H28 N2 O4 ' _chemical_formula_sum 'C23 H28 N2 O4 ' _chemical_name_systematic ; ? ; _cell_length_a 5.8530(2) _cell_length_b 9.3810(5) _cell_length_c 40.728(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2236.3(2) _diffrn_reflns_number 2073 _diffrn_reflns_theta_max 26.33 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_full 26.33 _diffrn_measurement_method 'IP' _computing_cell_refinement 'HKL Scalepack' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.08 _exptl_crystal_F_000 848 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' # Refinement statistics _reflns_d_resolution_low 2.14 _reflns_d_resolution_high 0.63 _reflns_limit_h_max 6 _reflns_limit_h_min 0 _reflns_limit_k_max 11 _reflns_limit_k_min 0 _reflns_limit_l_max 50 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_shift/su_max 0.175 _refine_ls_shift/su_mean 0.032 _reflns_number_total 2050 _refine_ls_R_factor_all 0.095 _refine_ls_wR_factor_all 0.126 _refine_ls_goodness_of_fit_all 0.902 _refine_ls_number_reflns 1843 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_number_constraints 28 _refine_ls_wR_factor_ref 0.126 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_abs_structure_details ; ; _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = exp ( 0.10 sin(\q)/\l^2^ )/ s^2^(Fo^2^) + 0.01000 * Fo^2^ ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maXus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens 'geom, diff' _refine_diff_density_max 0.19 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.06 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.2093(5) 0.1848(4) 0.77850(8) 0.086(2) 1.00 Uij O2 0.1984(5) 0.1996(4) 0.72255(9) 0.097(3) 1.00 Uij N3 0.7729(7) -0.2020(6) 0.90612(10) 0.096(3) 1.00 Uij O4 -0.0800(5) 0.2777(4) 0.75251(9) 0.114(3) 1.00 Uij N5 0.5758(7) -0.2010(5) 0.89401(10) 0.088(3) 1.00 Uij C6 0.4448(7) 0.1296(5) 0.77805(12) 0.070(3) 1.00 Uij C7 0.3090(7) -0.0424(6) 0.82201(12) 0.074(3) 1.00 Uij C8 0.4247(8) 0.1301(5) 0.71761(13) 0.078(3) 1.00 Uij C9 0.4750(6) 0.0416(5) 0.74727(12) 0.071(3) 1.00 Uij O10 0.8996(8) -0.5620(5) 1.01284(11) 0.140(4) 1.00 Uij C11 0.3464(7) -0.1203(6) 0.85007(12) 0.079(3) 1.00 Uij C12 0.5532(8) -0.1110(6) 0.86580(12) 0.075(3) 1.00 Uij C13 0.1034(8) 0.2228(6) 0.75069(17) 0.088(4) 1.00 Uij C14 0.7228(7) -0.0209(6) 0.85393(13) 0.085(3) 1.00 Uij C15 0.7979(9) -0.2947(7) 0.93397(13) 0.088(4) 1.00 Uij C16 0.6833(8) 0.0575(6) 0.82581(13) 0.084(3) 1.00 Uij C17 0.4747(7) 0.0478(6) 0.80936(11) 0.068(3) 1.00 Uij C18 0.6348(10) -0.3927(8) 0.94388(14) 0.106(4) 1.00 Uij C19 0.6338(11) -0.0061(7) 0.67422(13) 0.107(4) 1.00 Uij C20 0.8806(12) -0.4678(8) 0.98727(15) 0.107(5) 1.00 Uij C21 0.4052(10) 0.0499(6) 0.68606(13) 0.096(4) 1.00 Uij C22 0.9996(9) -0.2849(8) 0.95120(15) 0.112(4) 1.00 Uij C23 0.6741(10) -0.4799(9) 0.97036(15) 0.120(5) 1.00 Uij C24 1.0404(11) -0.3705(9) 0.97807(16) 0.116(5) 1.00 Uij C25 0.6125(14) -0.0801(8) 0.64112(15) 0.135(6) 1.00 Uij C26 0.8276(16) -0.1364(10) 0.62754(17) 0.166(7) 1.00 Uij C27 1.1012(15) -0.5677(10) 1.03049(18) 0.178(7) 1.00 Uij C30 0.800(2) -0.2170(13) 0.59453(19) 0.219(10) 1.00 Uij C31 0.982(2) -0.2698(13) 0.5777(2) 0.288(14) 1.00 Uij H9A 0.629114 0.005867 0.748341 0.075376 1.00 Uiso H9B 0.412396 -0.061457 0.749306 0.075376 1.00 Uiso H8 0.539342 0.232215 0.718698 0.083557 1.00 Uiso H6 0.565833 0.231203 0.777356 0.076278 1.00 Uiso H27A 1.090310 -0.637578 1.047629 0.183510 1.00 Uiso H27B 1.128554 -0.475553 1.039972 0.183510 1.00 Uiso H27C 1.224922 -0.591890 1.016060 0.183510 1.00 Uiso H21A 0.308902 -0.031310 0.689864 0.101273 1.00 Uiso H21B 0.336146 0.110462 0.669865 0.101273 1.00 Uiso H19A 0.728494 0.076729 0.671647 0.113827 1.00 Uiso H19B 0.698165 -0.067244 0.690698 0.113827 1.00 Uiso H25A 0.516460 -0.161775 0.644411 0.137450 1.00 Uiso H25B 0.542888 -0.017432 0.625389 0.137450 1.00 Uiso H26A 0.918221 -0.053984 0.622435 0.162572 1.00 Uiso H26B 0.902557 -0.191324 0.644249 0.162572 1.00 Uiso H11 0.218469 -0.197742 0.857009 0.084257 1.00 Uiso H16 0.804549 0.129265 0.817248 0.090357 1.00 Uiso H7 0.164662 -0.051798 0.811038 0.079768 1.00 Uiso H14 0.864707 -0.014971 0.865678 0.090038 1.00 Uiso H18 0.494147 -0.399042 0.931845 0.111066 1.00 Uiso H23 0.557634 -0.544807 0.977570 0.124794 1.00 Uiso H24 1.179056 -0.362790 0.990537 0.120345 1.00 Uiso H22 1.111168 -0.217057 0.943842 0.117472 1.00 Uiso H30A 0.716151 -0.300960 0.597539 0.224238 1.00 Uiso H30B 0.719829 -0.156855 0.578055 0.224238 1.00 Uiso H31A 0.930835 -0.314681 0.557837 0.379484 1.00 Uiso H31B 1.062325 -0.334311 0.591065 0.379484 1.00 Uiso H31C 1.080838 -0.190159 0.571775 0.379484 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0733(18) 0.080(3) 0.104(2) 0.0260(19) -.0035(18) 0.001(2) O2 0.094(2) 0.096(4) 0.102(3) 0.028(2) -.004(2) 0.018(2) N3 0.091(3) 0.110(4) 0.087(3) 0.004(3) -.001(2) -.002(3) O4 0.076(2) 0.109(4) 0.158(3) 0.023(2) 0.002(2) 0.022(3) N5 0.080(2) 0.108(4) 0.076(3) 0.006(2) -.005(2) -.007(3) C6 0.057(2) 0.056(4) 0.098(4) 0.007(2) -.001(2) -.009(3) C7 0.064(3) 0.072(4) 0.086(3) -.006(3) -.004(2) -.001(3) C8 0.086(3) 0.058(4) 0.090(4) 0.005(3) 0.002(3) 0.005(3) C9 0.075(2) 0.048(4) 0.089(3) 0.007(2) -.002(2) 0.004(3) O10 0.144(4) 0.168(5) 0.108(3) -.007(3) -.025(3) 0.040(3) C11 0.072(3) 0.076(4) 0.087(3) -.002(3) -.004(2) 0.000(3) C12 0.082(3) 0.072(4) 0.069(3) 0.004(3) -.003(2) -.007(3) C13 0.072(3) 0.067(4) 0.126(5) 0.000(3) -.004(4) 0.007(4) C14 0.071(3) 0.092(5) 0.091(3) -.003(3) -.009(3) 0.000(3) C15 0.097(4) 0.089(5) 0.077(4) 0.010(4) 0.005(3) 0.005(3) C16 0.075(3) 0.077(5) 0.102(4) -.004(3) -.003(3) 0.006(3) C17 0.062(3) 0.064(4) 0.077(3) 0.006(2) -.005(2) -.007(3) C18 0.113(4) 0.116(6) 0.090(4) -.005(4) -.005(3) 0.006(4) C19 0.151(5) 0.084(5) 0.086(4) 0.003(4) 0.013(4) 0.014(3) C20 0.125(5) 0.113(7) 0.084(4) 0.010(5) -.003(4) 0.008(4) C21 0.116(4) 0.090(5) 0.084(4) 0.006(4) -.004(3) 0.012(3) C22 0.102(4) 0.128(7) 0.106(4) -.009(4) -.015(3) 0.029(4) C23 0.110(4) 0.152(7) 0.099(4) -.014(4) -.005(3) 0.016(5) C24 0.115(5) 0.132(7) 0.101(5) -.008(4) -.030(4) 0.018(4) C25 0.194(7) 0.124(7) 0.088(4) 0.029(6) 0.005(5) 0.005(4) C26 0.222(8) 0.168(8) 0.109(6) 0.028(7) 0.038(6) -.006(6) C27 0.202(8) 0.195(10) 0.138(6) -.040(7) -.054(6) 0.054(6) C30 0.314(13) 0.224(11) 0.120(7) 0.055(10) 0.044(7) -.039(7) C31 0.351(17) 0.277(16) 0.236(12) 0.078(14) 0.101(11) -.028(11) 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 C6 O1 C13 O2 6.3(4) . . . . ? C6 O1 C13 O4 -174.0(7) . . . . ? C13 O1 C6 C9 -35.4(4) . . . . ? C13 O1 C6 C17 -158.6(6) . . . . ? C8 O2 C13 O1 0.6(4) . . . . ? C8 O2 C13 O4 -179.1(8) . . . . ? C13 O2 C8 C9 22.9(5) . . . . ? C13 O2 C8 C21 147.0(6) . . . . ? C15 N3 N5 C12 -178.6(6) . . . . ? N5 N3 C15 C18 10.2(5) . . . . ? N5 N3 C15 C22 -170.8(7) . . . . ? N3 N5 C12 C11 173.2(6) . . . . ? N3 N5 C12 C14 -5.9(5) . . . . ? C12 N5 N3 C15 -178.6(6) . . . . ? O1 C6 C9 C8 57.7(4) . . . . ? C9 C6 O1 C13 -35.4(4) . . . . ? O1 C6 C17 C7 42.0(4) . . . . ? C17 C6 O1 C13 -158.6(6) . . . . ? O1 C6 C17 C16 -141.1(5) . . . . ? C9 C6 C17 C7 -77.2(5) . . . . ? C17 C6 C9 C8 175.8(5) . . . . ? C9 C6 C17 C16 99.7(5) . . . . ? C11 C7 C17 C6 177.2(7) . . . . ? C17 C7 C11 C12 -1.1(5) . . . . ? C11 C7 C17 C16 0.3(5) . . . . ? O2 C8 C9 C6 -51.1(4) . . . . ? C9 C8 O2 C13 22.9(5) . . . . ? C21 C8 O2 C13 147.0(6) . . . . ? O2 C8 C21 C19 169.8(6) . . . . ? C21 C8 C9 C6 -169.0(6) . . . . ? C9 C8 C21 C19 -70.9(5) . . . . ? C8 C9 C6 O1 57.7(4) . . . . ? C6 C9 C8 O2 -51.1(4) . . . . ? C8 C9 C6 C17 175.8(5) . . . . ? C6 C9 C8 C21 -169.0(6) . . . . ? C27 O10 C20 C23 176.1(9) . . . . ? C27 O10 C20 C24 -3.7(7) . . . . ? C7 C11 C12 N5 -177.7(7) . . . . ? C7 C11 C12 C14 1.5(5) . . . . ? C12 C11 C7 C17 -1.1(5) . . . . ? C11 C12 N5 N3 173.2(6) . . . . ? N5 C12 C11 C7 -177.7(7) . . . . ? C14 C12 N5 N3 -5.9(5) . . . . ? N5 C12 C14 C16 177.9(8) . . . . ? C14 C12 C11 C7 1.5(5) . . . . ? C11 C12 C14 C16 -1.2(5) . . . . ? O2 C13 O1 C6 6.3(4) . . . . ? O1 C13 O2 C8 0.6(4) . . . . ? O4 C13 O1 C6 -174.0(7) . . . . ? O4 C13 O2 C8 -179.1(8) . . . . ? C16 C14 C12 N5 177.9(8) . . . . ? C16 C14 C12 C11 -1.2(5) . . . . ? C12 C14 C16 C17 0.4(5) . . . . ? C18 C15 N3 N5 10.2(5) . . . . ? N3 C15 C18 C23 178.5(9) . . . . ? C22 C15 N3 N5 -170.8(7) . . . . ? N3 C15 C22 C24 -179.3(9) . . . . ? C22 C15 C18 C23 -0.5(6) . . . . ? C18 C15 C22 C24 -0.3(6) . . . . ? C14 C16 C17 C6 -177.0(7) . . . . ? C14 C16 C17 C7 0.0(5) . . . . ? C17 C16 C14 C12 0.4(5) . . . . ? C7 C17 C6 O1 42.0(4) . . . . ? C7 C17 C6 C9 -77.2(5) . . . . ? C6 C17 C7 C11 177.2(7) . . . . ? C16 C17 C6 O1 -141.1(5) . . . . ? C16 C17 C6 C9 99.7(5) . . . . ? C6 C17 C16 C14 -177.0(7) . . . . ? C16 C17 C7 C11 0.3(5) . . . . ? C7 C17 C16 C14 0.0(5) . . . . ? C23 C18 C15 N3 178.5(9) . . . . ? C15 C18 C23 C20 0.3(6) . . . . ? C23 C18 C15 C22 -0.5(6) . . . . ? O10 C20 C23 C18 -179.1(9) . . . . ? C23 C20 O10 C27 176.1(9) . . . . ? O10 C20 C24 C22 178.4(11) . . . . ? C24 C20 O10 C27 -3.7(7) . . . . ? C24 C20 C23 C18 0.7(7) . . . . ? C23 C20 C24 C22 -1.5(6) . . . . ? C19 C21 C8 O2 169.8(6) . . . . ? C19 C21 C8 C9 -70.9(5) . . . . ? C24 C22 C15 N3 -179.3(9) . . . . ? C24 C22 C15 C18 -0.3(6) . . . . ? C15 C22 C24 C20 1.3(6) . . . . ? C18 C23 C20 O10 -179.1(9) . . . . ? C20 C23 C18 C15 0.3(6) . . . . ? C18 C23 C20 C24 0.7(7) . . . . ? C22 C24 C20 O10 178.4(11) . . . . ? C20 C24 C22 C15 1.3(6) . . . . ? C22 C24 C20 C23 -1.5(6) . . . . ? C13 O1 C6 H6 83.0(5) . . . . ? C13 O2 C8 H8 -89.4(5) . . . . ? O1 C6 C9 H9A -178.5(5) . . . . ? O1 C6 C9 H9B -81.5(4) . . . . ? H6 C6 O1 C13 83.0(5) . . . . ? C17 C6 C9 H9A -60.4(4) . . . . ? C17 C6 C9 H9B 36.6(4) . . . . ? H6 C6 C9 C8 -57.9(4) . . . . ? H6 C6 C9 H9A 65.9(4) . . . . ? H6 C6 C9 H9B 162.9(6) . . . . ? H6 C6 C17 C7 156.9(6) . . . . ? H6 C6 C17 C16 -26.2(4) . . . . ? C17 C7 C11 H11 -172.9(7) . . . . ? H7 C7 C11 C12 178.6(7) . . . . ? H7 C7 C11 H11 6.8(4) . . . . ? H7 C7 C17 C6 -2.5(4) . . . . ? H7 C7 C17 C16 -179.4(7) . . . . ? O2 C8 C9 H9A -169.3(6) . . . . ? O2 C8 C9 H9B 84.7(5) . . . . ? O2 C8 C21 H21A -72.3(5) . . . . ? O2 C8 C21 H21B 46.4(5) . . . . ? H8 C8 O2 C13 -89.4(5) . . . . ? C21 C8 C9 H9A 72.8(5) . . . . ? C21 C8 C9 H9B -33.2(5) . . . . ? C9 C8 C21 H21A 46.9(5) . . . . ? C9 C8 C21 H21B 165.7(7) . . . . ? H8 C8 C9 C6 54.5(4) . . . . ? H8 C8 C9 H9A -63.8(5) . . . . ? H8 C8 C9 H9B -169.8(6) . . . . ? H8 C8 C21 C19 60.6(5) . . . . ? H8 C8 C21 H21A 178.4(7) . . . . ? H8 C8 C21 H21B -62.9(5) . . . . ? C6 C9 C8 H8 54.5(4) . . . . ? C8 C9 C6 H6 -57.9(4) . . . . ? H9A C9 C6 O1 -178.5(5) . . . . ? H9A C9 C6 C17 -60.4(4) . . . . ? H9A C9 C6 H6 65.9(4) . . . . ? H9B C9 C6 O1 -81.5(4) . . . . ? H9B C9 C6 C17 36.6(4) . . . . ? H9B C9 C6 H6 162.9(6) . . . . ? H9A C9 C8 O2 -169.3(6) . . . . ? H9A C9 C8 C21 72.8(5) . . . . ? H9A C9 C8 H8 -63.8(5) . . . . ? H9B C9 C8 O2 84.7(5) . . . . ? H9B C9 C8 C21 -33.2(5) . . . . ? H9B C9 C8 H8 -169.8(6) . . . . ? C20 O10 C27 H27A 179.7(10) . . . . ? C20 O10 C27 H27B 59.8(7) . . . . ? C20 O10 C27 H27C -59.7(7) . . . . ? C12 C11 C7 H7 178.6(7) . . . . ? H11 C11 C7 C17 -172.9(7) . . . . ? H11 C11 C7 H7 6.8(4) . . . . ? H11 C11 C12 N5 -6.2(4) . . . . ? H11 C11 C12 C14 173.0(8) . . . . ? N5 C12 C11 H11 -6.2(4) . . . . ? N5 C12 C14 H14 -2.2(5) . . . . ? C14 C12 C11 H11 173.0(8) . . . . ? C11 C12 C14 H14 178.7(8) . . . . ? C12 C14 C16 H16 176.8(8) . . . . ? H14 C14 C12 N5 -2.2(5) . . . . ? H14 C14 C12 C11 178.7(8) . . . . ? H14 C14 C16 C17 -179.5(8) . . . . ? H14 C14 C16 H16 -3.1(5) . . . . ? N3 C15 C18 H18 -1.2(5) . . . . ? N3 C15 C22 H22 0.3(5) . . . . ? C22 C15 C18 H18 179.8(9) . . . . ? C18 C15 C22 H22 179.4(9) . . . . ? C17 C16 C14 H14 -179.5(8) . . . . ? H16 C16 C14 C12 176.8(8) . . . . ? H16 C16 C14 H14 -3.1(5) . . . . ? H16 C16 C17 C6 6.5(4) . . . . ? H16 C16 C17 C7 -176.5(7) . . . . ? C7 C17 C6 H6 156.9(6) . . . . ? C6 C17 C7 H7 -2.5(4) . . . . ? C16 C17 C6 H6 -26.2(4) . . . . ? C6 C17 C16 H16 6.5(4) . . . . ? C7 C17 C16 H16 -176.5(7) . . . . ? C16 C17 C7 H7 -179.4(7) . . . . ? C15 C18 C23 H23 177.5(10) . . . . ? H18 C18 C15 N3 -1.2(5) . . . . ? H18 C18 C15 C22 179.8(9) . . . . ? H18 C18 C23 C20 180.0(10) . . . . ? H18 C18 C23 H23 -2.8(6) . . . . ? H19A C19 C21 C8 -59.1(5) . . . . ? H19A C19 C21 H21A -177.3(7) . . . . ? H19A C19 C21 H21B 63.2(6) . . . . ? H19B C19 C21 C8 58.5(5) . . . . ? H19B C19 C21 H21A -59.7(6) . . . . ? H19B C19 C21 H21B -179.2(8) . . . . ? O10 C20 C23 H23 3.7(6) . . . . ? O10 C20 C24 H24 -1.8(6) . . . . ? C24 C20 C23 H23 -176.5(11) . . . . ? C23 C20 C24 H24 178.3(11) . . . . ? C19 C21 C8 H8 60.6(5) . . . . ? C8 C21 C19 H19A -59.1(5) . . . . ? C8 C21 C19 H19B 58.5(5) . . . . ? H21A C21 C8 O2 -72.3(5) . . . . ? H21A C21 C8 C9 46.9(5) . . . . ? H21A C21 C8 H8 178.4(7) . . . . ? H21B C21 C8 O2 46.4(5) . . . . ? H21B C21 C8 C9 165.7(7) . . . . ? H21B C21 C8 H8 -62.9(5) . . . . ? H21A C21 C19 H19A -177.3(7) . . . . ? H21A C21 C19 H19B -59.7(6) . . . . ? H21B C21 C19 H19A 63.2(6) . . . . ? H21B C21 C19 H19B -179.2(8) . . . . ? C15 C22 C24 H24 -178.5(11) . . . . ? H22 C22 C15 N3 0.3(5) . . . . ? H22 C22 C15 C18 179.4(9) . . . . ? H22 C22 C24 C20 -178.4(11) . . . . ? H22 C22 C24 H24 1.8(7) . . . . ? C20 C23 C18 H18 180.0(10) . . . . ? H23 C23 C18 C15 177.5(10) . . . . ? H23 C23 C18 H18 -2.8(6) . . . . ? H23 C23 C20 O10 3.7(6) . . . . ? H23 C23 C20 C24 -176.5(11) . . . . ? C20 C24 C22 H22 -178.4(11) . . . . ? H24 C24 C20 O10 -1.8(6) . . . . ? H24 C24 C20 C23 178.3(11) . . . . ? H24 C24 C22 C15 -178.5(11) . . . . ? H24 C24 C22 H22 1.8(7) . . . . ? H25A C25 C26 H26A 175.0(9) . . . . ? H25A C25 C26 H26B -67.8(8) . . . . ? H25B C25 C26 H26A 57.4(8) . . . . ? H25B C25 C26 H26B 174.5(10) . . . . ? H26A C26 C25 H25A 175.0(9) . . . . ? H26A C26 C25 H25B 57.4(8) . . . . ? H26B C26 C25 H25A -67.8(8) . . . . ? H26B C26 C25 H25B 174.5(10) . . . . ? H27A C27 O10 C20 179.7(10) . . . . ? H27B C27 O10 C20 59.8(7) . . . . ? H27C C27 O10 C20 -59.7(7) . . . . ? H30A C30 C31 H31A 58.9(11) . . . . ? H30A C30 C31 H31B -63.6(12) . . . . ? H30A C30 C31 H31C 176.8(14) . . . . ? H30B C30 C31 H31A -53.3(11) . . . . ? H30B C30 C31 H31B -175.8(14) . . . . ? H30B C30 C31 H31C 64.6(11) . . . . ? H31A C31 C30 H30A 58.9(11) . . . . ? H31A C31 C30 H30B -53.3(11) . . . . ? H31B C31 C30 H30A -63.6(12) . . . . ? H31B C31 C30 H30B -175.8(14) . . . . ? H31C C31 C30 H30A 176.8(14) . . . . ? H31C C31 C30 H30B 64.6(11) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.473(12) . . ? O1 C13 1.339(15) . . ? O2 C8 1.490(13) . . ? O2 C13 1.29(2) . . ? N3 N5 1.255(12) . . ? N3 C15 1.44(2) . . ? O4 C13 1.193(13) . . ? N5 C12 1.43(2) . . ? C6 C9 1.51(2) . . ? C6 C17 1.50(2) . . ? C7 C11 1.37(2) . . ? C7 C17 1.386(15) . . ? C8 C9 1.49(2) . . ? C8 C21 1.49(2) . . ? O10 C20 1.37(2) . . ? O10 C27 1.38(2) . . ? C11 C12 1.372(14) . . ? C12 C14 1.39(2) . . ? C14 C16 1.38(2) . . ? C15 C18 1.39(2) . . ? C15 C22 1.38(2) . . ? C16 C17 1.396(15) . . ? C18 C23 1.37(2) . . ? C19 C21 1.52(2) . . ? C20 C23 1.40(2) . . ? C20 C24 1.36(2) . . ? C22 C24 1.38(2) . . ? C25 C26 1.47(2) . . ? C30 C31 1.36(3) . . ? C6 H6 1.188(13) . . ? C7 H7 0.960(11) . . ? C8 H8 1.171(13) . . ? C9 H9A 0.963(10) . . ? C9 H9B 1.037(13) . . ? C11 H11 1.081(13) . . ? C14 H14 0.960(11) . . ? C16 H16 1.038(13) . . ? C18 H18 0.960(14) . . ? C19 H19A 0.96(2) . . ? C19 H19B 0.960(15) . . ? C21 H21A 0.96(2) . . ? C21 H21B 0.960(13) . . ? C22 H22 0.96(2) . . ? C23 H23 0.96(2) . . ? C24 H24 0.960(14) . . ? C25 H25A 0.96(2) . . ? C25 H25B 0.96(2) . . ? C26 H26A 0.96(2) . . ? C26 H26B 0.96(2) . . ? C27 H27A 0.96(2) . . ? C27 H27B 0.96(2) . . ? C27 H27C 0.96(2) . . ? C30 H30A 0.93(3) . . ? C30 H30B 0.99(3) . . ? C31 H31A 0.9595 . . ? C31 H31B 0.9407 . . ? C31 H31C 0.9757 . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C13 121.1(10) . . . ? C8 O2 C13 125.2(10) . . . ? N5 N3 C15 114.1(12) . . . ? N3 N5 C12 113.9(11) . . . ? O1 C6 C9 108.2(9) . . . ? O1 C6 C17 106.2(9) . . . ? C9 C6 C17 114.4(11) . . . ? C11 C7 C17 121.5(10) . . . ? O2 C8 C9 108.0(10) . . . ? O2 C8 C21 105.6(10) . . . ? C9 C8 C21 115.5(12) . . . ? C6 C9 C8 110.1(11) . . . ? C20 O10 C27 119.3(15) . . . ? C7 C11 C12 119.7(12) . . . ? N5 C12 C11 114.7(12) . . . ? N5 C12 C14 124.8(10) . . . ? C11 C12 C14 120.4(13) . . . ? O1 C13 O2 120.4(11) . . . ? O1 C13 O4 119.(2) . . . ? O2 C13 O4 121.0(15) . . . ? C12 C14 C16 119.5(10) . . . ? N3 C15 C18 124.2(12) . . . ? N3 C15 C22 116.7(14) . . . ? C18 C15 C22 119.1(14) . . . ? C14 C16 C17 120.7(12) . . . ? C6 C17 C7 123.2(10) . . . ? C6 C17 C16 118.5(11) . . . ? C7 C17 C16 118.3(11) . . . ? C15 C18 C23 120.6(14) . . . ? O10 C20 C23 113.(2) . . . ? O10 C20 C24 126.(2) . . . ? C23 C20 C24 121.(2) . . . ? C8 C21 C19 112.4(12) . . . ? C15 C22 C24 121.(2) . . . ? C18 C23 C20 119.(2) . . . ? C20 C24 C22 119.4(14) . . . ? O1 C6 H6 106.0(10) . . . ? C9 C6 H6 110.4(10) . . . ? C17 C6 H6 111.2(10) . . . ? C11 C7 H7 118.6(12) . . . ? C17 C7 H7 119.9(12) . . . ? O2 C8 H8 98.4(10) . . . ? C9 C8 H8 108.1(10) . . . ? C21 C8 H8 119.3(11) . . . ? C6 C9 H9A 105.2(10) . . . ? C6 C9 H9B 113.7(11) . . . ? C8 C9 H9A 114.5(11) . . . ? C8 C9 H9B 120.8(11) . . . ? H9A C9 H9B 90.2(10) . . . ? C7 C11 H11 117.7(11) . . . ? C12 C11 H11 122.1(13) . . . ? C12 C14 H14 118.6(14) . . . ? C16 C14 H14 121.9(14) . . . ? C14 C16 H16 120.6(12) . . . ? C17 C16 H16 118.6(13) . . . ? C15 C18 H18 119.(2) . . . ? C23 C18 H18 121.(2) . . . ? C21 C19 H19A 105.3(15) . . . ? C21 C19 H19B 109.3(13) . . . ? H19A C19 H19B 109.5(15) . . . ? C8 C21 H21A 107.8(12) . . . ? C8 C21 H21B 109.0(14) . . . ? C19 C21 H21A 107.2(14) . . . ? C19 C21 H21B 111.0(13) . . . ? H21A C21 H21B 109.5(14) . . . ? C15 C22 H22 118.(2) . . . ? C24 C22 H22 121.(2) . . . ? C18 C23 H23 120.(2) . . . ? C20 C23 H23 121.(2) . . . ? C20 C24 H24 119.(2) . . . ? C22 C24 H24 122.(2) . . . ? C26 C25 H25A 105.(2) . . . ? C26 C25 H25B 109.(2) . . . ? H25A C25 H25B 109.(2) . . . ? C25 C26 H26A 105.(2) . . . ? C25 C26 H26B 108.(2) . . . ? H26A C26 H26B 109.(2) . . . ? O10 C27 H27A 110.(2) . . . ? O10 C27 H27B 108.(2) . . . ? O10 C27 H27C 110.(2) . . . ? H27A C27 H27B 109.(2) . . . ? H27A C27 H27C 109.(2) . . . ? H27B C27 H27C 109.(2) . . . ? C31 C30 H30A 100.(2) . . . ? C31 C30 H30B 104.(2) . . . ? H30A C30 H30B 109.(3) . . . ? C30 C31 H31A 109.9(12) . . . ? C30 C31 H31B 109.6(11) . . . ? C30 C31 H31C 108.2(13) . . . ? H31A C31 H31B 111.1710 . . . ? H31A C31 H31C 108.2059 . . . ? H31B C31 H31C 109.7639 . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 H19B 2.698(9) 1_555 4_656 ? O1 H16 2.894(8) 1_555 1_455 ? N3 H27B 2.883(11) 1_555 3_447 ? O4 H9B 2.463(9) 1_555 4_556 ? O4 H8 2.653(9) 1_555 1_455 ? O4 H6 2.347(9) 1_555 1_455 ? C7 H8 2.829(12) 1_555 4_646 ? O10 H31A 2.905(12) 1_555 2_645 ? C11 H19A 3.009(14) 1_555 4_646 ? C15 H27B 2.92(2) 1_555 3_447 ? C23 H31C 2.98(2) 1_555 4_746 ? C31 H27A 2.9200 1_555 2_744 ? H9A H6 3.0060 1_555 4_646 ? H9B H8 2.3504 1_555 4_646 ? H9B H6 2.2313 1_555 4_646 ? H8 H7 2.9281 1_555 4_656 ? H6 H21A 2.6988 1_555 4_656 ? H6 H19B 2.7668 1_555 4_656 ? H27A H30A 2.7716 1_555 2_645 ? H27A H30B 2.9240 1_555 2_645 ? H27A H31A 2.8686 1_555 2_745 ? H27A H31B 2.7079 1_555 2_745 ? H27A H31C 2.6988 1_555 2_745 ? H27C H23 2.5386 1_555 1_655 ? H27C H31A 2.7790 1_555 2_745 ? H19A H11 2.4361 1_555 4_656 ? H25B H18 2.5912 1_555 4_656 ? H26B H16 2.8689 1_555 4_746 ? H11 H14 2.7114 1_555 1_455 ? H16 H7 2.7188 1_555 1_655 ? H7 H14 2.8555 1_555 1_455 ? H14 H31B 2.4816 1_555 4_756 ? H18 H24 3.0382 1_555 1_455 ? H18 H22 2.8597 1_555 1_455 ? H18 H30B 2.7533 1_555 4_646 ? H23 H24 2.8468 1_555 1_455 ? H23 H30B 2.9791 1_555 4_646 ? O1 H19B 2.698(9) 1_555 4_656 ? O1 H16 2.894(8) 1_555 1_455 ? N3 H27B 2.883(11) 1_555 3_447 ? O4 H9B 2.463(9) 1_555 4_556 ? O4 H8 2.653(9) 1_555 1_455 ? O4 H6 2.347(9) 1_555 1_455 ? C7 H8 2.829(12) 1_555 4_646 ? O10 H31A 2.905(12) 1_555 2_645 ? C11 H19A 3.009(14) 1_555 4_646 ? C15 H27B 2.92(2) 1_555 3_447 ? C23 H31C 2.98(2) 1_555 4_746 ? C31 H27A 2.9200 1_555 2_744 ? H9A H6 3.0060 1_555 4_646 ? H9B H8 2.3504 1_555 4_646 ? H9B H6 2.2313 1_555 4_646 ? H8 H7 2.9281 1_555 4_656 ? H6 H21A 2.6988 1_555 4_656 ? H6 H19B 2.7668 1_555 4_656 ? H27A H30A 2.7716 1_555 2_645 ? H27A H30B 2.9240 1_555 2_645 ? H27A H31A 2.8686 1_555 2_745 ? H27A H31B 2.7079 1_555 2_745 ? H27A H31C 2.6988 1_555 2_745 ? H27C H23 2.5386 1_555 1_655 ? H27C H31A 2.7790 1_555 2_745 ? H19A H11 2.4361 1_555 4_656 ? H25B H18 2.5912 1_555 4_656 ? H26B H16 2.8689 1_555 4_746 ? H11 H14 2.7114 1_555 1_455 ? H16 H7 2.7188 1_555 1_655 ? H7 H14 2.8555 1_555 1_455 ? H14 H31B 2.4816 1_555 4_756 ? H18 H24 3.0382 1_555 1_455 ? H18 H22 2.8597 1_555 1_455 ? H18 H30B 2.7533 1_555 4_646 ? H23 H24 2.8468 1_555 1_455 ? H23 H30B 2.9791 1_555 4_646 ? #===================================================