# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_chromophore1 _database_code_CSD 190459 _journal_coden_Cambridge 188 loop_ _publ_author_name 'Centore, Roberto' 'Carella, Antonio' 'Castaldo, Anna' 'Fort, Alain' 'Sirigu, Augusto' 'Tuzi, Angela' _publ_contact_author_name 'Dr Roberto Centore' _publ_contact_author_address ; Dipartmento di Chimica Universita di Napoli "Federico II" Via Cinthia Napoli I 80126 ITALY ; _publ_contact_author_email 'CENTORE@CHEMISTRY.UNINA.IT' _publ_requested_journal 'Perkin Transactions 2' _publ_section_title ; Synthesis and second order nonlinear optical properties of new chromophores containing 1,3,4-oxadiazole and thiophene rings. ; _publ_contact_letter ; Dear sir, this file contains CIF-format data for the crystal structure reported in the paper entitled "Synthesis and second order nonlinear optical properties of new chromophores containing 1,3,4-oxadiazole and thiophene rings", by A. Carella, A. Castaldo, R. Centore, A. Fort, A. Sirigu, A. Tuzi, submitted for publication on Journal of the Chemical Society Perkin Transactions 2. Regards R. Centore ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-{4-[4-(N,N-diacetyloxyamino)phenylazo]phenyl}- 5-(4-nitrophenyl)-[1,3,4]-oxadiazole ; _chemical_formula_moiety 'C28 H26 N6 O7' _chemical_formula_sum 'C28 H26 N6 O7' _chemical_formula_weight 558.55 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 orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.171(3) _cell_length_b 11.543(2) _cell_length_c 65.146(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5392(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 17.95 _cell_measurement_theta_max 21.91 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.846 _exptl_absorpt_correction_type none _exptl_special_details ; crystals obtained by slow evaporation from N,N-dimethylformamide solution. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Nonius CAD4 goniometer ; _diffrn_measurement_method \w/2\q scans _diffrn_standards_number 1 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3978 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1765 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 73 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 59.88 _diffrn_special_details ; Systematically absent reflections were not measured during data collection.Data collection was not extended beyond theta 60 degrees because Weissenberg photographs indicated poor diffraction pattern at high sintheta/lam. ; _reflns_number_total 3978 _reflns_number_gt 1362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Nonius, 1996)' _computing_cell_refinement 'CELLFIT (R. Centore, 2002)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1999)' _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 sigma _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1420P)^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_number_reflns 3978 _refine_ls_number_parameters 370 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2809 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2893 _refine_ls_wR_factor_gt 0.2046 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0.040 _refine_ls_shift/su_mean 0.007 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 O1 O 0.4538(9) 0.3387(5) 0.11584(9) 0.086(2) Uani 1 d . . . O2 O 0.3824(9) 0.5017(5) 0.13030(9) 0.087(2) Uani 1 d . . . O3 O 0.3905(6) 0.2262(4) 0.22618(7) 0.0470(13) Uani 1 d . . . N1 N 0.4155(10) 0.3988(6) 0.13135(10) 0.0611(19) Uani 1 d . . . N2 N 0.3343(9) 0.0615(5) 0.21040(9) 0.0584(18) Uani 1 d . . . N3 N 0.3294(9) 0.0419(5) 0.23186(10) 0.0562(18) Uani 1 d . . . N4 N 0.3808(9) 0.2284(6) 0.32555(8) 0.0527(17) Uani 1 d . . . N5 N 0.3651(8) 0.3333(5) 0.33083(9) 0.0512(17) Uani 1 d . . . C1 C 0.4067(10) 0.3405(7) 0.15145(11) 0.052(2) Uani 1 d . . . C2 C 0.4071(10) 0.4054(7) 0.16896(11) 0.053(2) Uani 1 d . . . H2 H 0.4130 0.4857 0.1683 0.064 Uiso 1 calc R . . C3 C 0.3985(11) 0.3496(6) 0.18781(12) 0.056(2) Uani 1 d . . . H3 H 0.4008 0.3927 0.1999 0.067 Uiso 1 calc R . . C4 C 0.3864(10) 0.2304(6) 0.18872(11) 0.0447(18) Uani 1 d . . . C5 C 0.3863(11) 0.1663(6) 0.17066(11) 0.055(2) Uani 1 d . . . H5 H 0.3801 0.0860 0.1713 0.066 Uiso 1 calc R . . C6 C 0.3950(11) 0.2197(6) 0.15203(12) 0.059(2) Uani 1 d . . . H6 H 0.3933 0.1767 0.1400 0.070 Uiso 1 calc R . . C7 C 0.3736(10) 0.1704(6) 0.20788(11) 0.0426(18) Uani 1 d . . . C8 C 0.3623(10) 0.1406(6) 0.24008(11) 0.0435(18) Uani 1 d . . . C9 C 0.3679(10) 0.1680(6) 0.26181(11) 0.0484(19) Uani 1 d . . . C10 C 0.4195(10) 0.2755(6) 0.26931(11) 0.049(2) Uani 1 d . . . H10 H 0.4522 0.3336 0.2601 0.058 Uiso 1 calc R . . C11 C 0.4238(11) 0.2988(7) 0.28999(10) 0.053(2) Uani 1 d . . . H11 H 0.4594 0.3717 0.2946 0.064 Uiso 1 calc R . . C12 C 0.3750(10) 0.2136(6) 0.30387(11) 0.0487(19) Uani 1 d . . . C13 C 0.3255(10) 0.1048(6) 0.29668(11) 0.052(2) Uani 1 d . . . H13 H 0.2950 0.0468 0.3060 0.062 Uiso 1 calc R . . C14 C 0.3209(10) 0.0812(6) 0.27587(12) 0.054(2) Uani 1 d . . . H14 H 0.2867 0.0080 0.2712 0.065 Uiso 1 calc R . . C15 C 0.3879(10) 0.3541(7) 0.35241(10) 0.0483(19) Uani 1 d . . . C16 C 0.3533(10) 0.4672(6) 0.35856(10) 0.049(2) Uani 1 d . . . H16 H 0.3084 0.5210 0.3492 0.059 Uiso 1 calc R . . C17 C 0.3855(11) 0.4995(7) 0.37848(11) 0.060(2) Uani 1 d . . . H17 H 0.3558 0.5744 0.3826 0.072 Uiso 1 calc R . . C18 C 0.4619(12) 0.4226(7) 0.39283(11) 0.060(2) Uani 1 d . . . C19 C 0.4887(11) 0.3084(7) 0.38637(13) 0.066(2) Uani 1 d . . . H19 H 0.5332 0.2536 0.3956 0.079 Uiso 1 calc R . . C20 C 0.4505(10) 0.2757(7) 0.36655(11) 0.054(2) Uani 1 d . . . H20 H 0.4674 0.1988 0.3627 0.065 Uiso 1 calc R . . N6 N 0.5083(12) 0.4598(7) 0.41204(10) 0.085(3) Uani 1 d . . . O6 O 0.7774(16) 0.2802(9) 0.44810(12) 0.174(5) Uani 1 d D . . C25 C 0.555(2) 0.3761(12) 0.4295(2) 0.158(6) Uani 1 d . . . H25A H 0.4976 0.4025 0.4422 0.190 Uiso 1 calc R . . H25B H 0.5073 0.2994 0.4264 0.190 Uiso 1 calc R . . O7 O 0.7056(19) 0.3887(11) 0.47361(15) 0.210(6) Uani 1 d . . . O4 O 0.273(3) 0.5606(14) 0.44304(13) 0.286(11) Uani 1 d . . . C22 C 0.317(2) 0.6179(12) 0.42508(16) 0.146(6) Uani 1 d . . . H22A H 0.3209 0.7008 0.4275 0.175 Uiso 1 calc R . . H22B H 0.2223 0.6026 0.4148 0.175 Uiso 1 calc R . . C21 C 0.496(2) 0.5788(10) 0.41776(16) 0.124(5) Uani 1 d . . . H21A H 0.5301 0.6255 0.4060 0.148 Uiso 1 calc R . . H21B H 0.5876 0.5934 0.4284 0.148 Uiso 1 calc R . . C28 C 0.8298(19) 0.2031(11) 0.48069(16) 0.149(5) Uani 1 d . . . H28A H 0.8651 0.1371 0.4726 0.224 Uiso 1 calc R . . H28B H 0.7338 0.1812 0.4902 0.224 Uiso 1 calc R . . H28C H 0.9363 0.2311 0.4881 0.224 Uiso 1 calc R . . C27 C 0.761(2) 0.2938(14) 0.4673(2) 0.134(5) Uani 1 d . . . O5 O 0.172(4) 0.663(2) 0.4566(3) 0.63(3) Uani 1 d D . . C26 C 0.747(3) 0.3727(13) 0.4317(2) 0.176(7) Uani 1 d D . . H26A H 0.7950 0.4471 0.4361 0.211 Uiso 1 calc R . . H26B H 0.8063 0.3510 0.4189 0.211 Uiso 1 calc R . . C24 C 0.172(2) 0.5097(12) 0.47549(18) 0.172(6) Uani 1 d . . . H24A H 0.1769 0.4277 0.4730 0.258 Uiso 1 calc R . . H24B H 0.0523 0.5301 0.4809 0.258 Uiso 1 calc R . . H24C H 0.2673 0.5304 0.4852 0.258 Uiso 1 calc R . . C23 C 0.203(3) 0.569(2) 0.4570(3) 0.209(11) Uani 1 d 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 O1 0.088(5) 0.101(5) 0.068(4) -0.012(4) 0.001(4) -0.003(4) O2 0.107(6) 0.066(4) 0.089(4) 0.007(3) -0.019(4) 0.000(4) O3 0.041(3) 0.043(3) 0.057(3) -0.010(2) -0.005(3) 0.004(3) N1 0.048(5) 0.069(5) 0.067(5) 0.000(4) -0.014(4) -0.007(4) N2 0.061(5) 0.051(4) 0.064(4) -0.015(3) 0.003(4) -0.002(4) N3 0.046(4) 0.044(3) 0.079(5) -0.012(3) -0.002(3) -0.001(3) N4 0.041(4) 0.063(4) 0.054(4) -0.002(3) 0.000(3) 0.000(4) N5 0.041(4) 0.049(4) 0.063(4) -0.002(3) 0.002(4) 0.001(4) C1 0.033(5) 0.069(5) 0.053(5) -0.002(4) -0.009(4) -0.006(4) C2 0.045(6) 0.048(4) 0.066(5) -0.014(4) -0.010(4) 0.004(4) C3 0.051(5) 0.053(5) 0.064(5) -0.013(4) -0.001(5) 0.004(4) C4 0.031(4) 0.043(4) 0.059(5) -0.011(4) -0.004(4) 0.000(4) C5 0.062(6) 0.044(4) 0.058(5) -0.009(4) 0.007(5) 0.005(4) C6 0.048(5) 0.051(5) 0.076(6) -0.017(4) 0.007(5) 0.000(5) C7 0.034(5) 0.040(4) 0.054(5) -0.015(3) -0.003(4) -0.003(4) C8 0.028(4) 0.042(4) 0.060(5) -0.005(4) -0.009(4) 0.005(4) C9 0.038(5) 0.041(4) 0.065(5) -0.001(4) 0.001(4) -0.007(4) C10 0.039(5) 0.037(4) 0.070(5) -0.003(4) 0.008(4) -0.010(4) C11 0.060(6) 0.048(4) 0.050(4) -0.011(4) -0.001(4) -0.001(4) C12 0.035(5) 0.052(5) 0.059(5) 0.001(4) 0.000(4) 0.005(4) C13 0.044(5) 0.051(5) 0.060(5) 0.010(4) 0.010(4) 0.001(4) C14 0.042(5) 0.046(4) 0.075(5) -0.007(4) 0.001(4) -0.004(4) C15 0.037(4) 0.064(5) 0.043(4) 0.008(4) 0.001(4) -0.002(4) C16 0.045(5) 0.047(4) 0.055(5) 0.005(4) 0.009(4) 0.001(4) C17 0.060(6) 0.069(5) 0.052(5) 0.000(4) 0.013(5) 0.003(5) C18 0.072(6) 0.069(5) 0.038(4) 0.005(4) 0.003(4) -0.012(5) C19 0.055(6) 0.076(6) 0.066(6) 0.016(5) -0.013(5) -0.008(5) C20 0.034(5) 0.063(5) 0.065(5) 0.005(4) -0.008(4) -0.006(4) N6 0.124(7) 0.083(5) 0.050(4) 0.004(4) -0.013(5) 0.008(6) O6 0.260(13) 0.179(9) 0.084(5) -0.003(6) -0.070(7) 0.089(9) C25 0.178(16) 0.115(11) 0.181(15) -0.041(10) -0.057(13) 0.036(12) O7 0.278(15) 0.193(10) 0.159(8) -0.056(8) -0.082(9) 0.077(11) O4 0.51(3) 0.286(15) 0.068(6) 0.049(8) 0.116(10) 0.190(16) C22 0.214(17) 0.154(12) 0.070(8) 0.005(8) 0.016(9) 0.073(12) C21 0.198(16) 0.090(8) 0.083(8) 0.003(7) -0.033(9) 0.005(10) C28 0.185(15) 0.159(12) 0.104(9) 0.031(8) -0.015(9) 0.036(11) C27 0.135(12) 0.125(11) 0.140(12) -0.027(11) -0.056(11) 0.050(10) O5 0.95(6) 0.53(4) 0.41(3) 0.35(3) 0.46(4) 0.51(4) C26 0.141(14) 0.197(16) 0.189(16) 0.030(13) 0.062(14) 0.042(14) C24 0.189(16) 0.214(15) 0.112(10) 0.005(10) 0.058(11) -0.019(13) C23 0.180(18) 0.25(2) 0.20(2) 0.16(2) 0.043(16) 0.096(16) _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. Some atoms of the two terminal aliphatic chains are thermally disordered, and two constraints were introduced during refinement (on bond lengths O6-C26 and O5-C23). Some bond lengths and angles involving these atoms do not fully agree with standard values. ; 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 N1 1.256(8) . no O2 N1 1.214(8) . no O3 C8 1.355(8) . no O3 C7 1.361(7) . no N1 C1 1.473(9) . no N2 C7 1.299(8) . no N2 N3 1.416(8) . no N3 C8 1.281(8) . no N4 N5 1.264(7) . no N4 C12 1.423(8) . no N5 C15 1.435(8) . no C1 C2 1.365(9) . no C1 C6 1.397(10) . no C2 C3 1.387(9) . no C2 H2 0.9300 . no C3 C4 1.380(9) . no C3 H3 0.9300 . no C4 C5 1.390(9) . no C4 C7 1.430(9) . no C5 C6 1.362(9) . no C5 H5 0.9300 . no C6 H6 0.9300 . no C8 C9 1.451(9) . no C9 C10 1.383(8) . no C9 C14 1.399(9) . no C10 C11 1.374(9) . no C10 H10 0.9300 . no C11 C12 1.380(9) . no C11 H11 0.9300 . no C12 C13 1.387(9) . no C13 C14 1.384(9) . no C13 H13 0.9300 . no C14 H14 0.9300 . no C15 C20 1.367(9) . no C15 C16 1.388(9) . no C16 C17 1.370(9) . no C16 H16 0.9300 . no C17 C18 1.400(10) . no C17 H17 0.9300 . no C18 N6 1.364(9) . no C18 C19 1.398(10) . no C19 C20 1.372(10) . no C19 H19 0.9300 . no C20 H20 0.9300 . no N6 C21 1.426(12) . no N6 C25 1.530(14) . no O6 C27 1.267(14) . no O6 C26 1.528(9) . no C25 C26 1.384(18) . no C25 H25A 0.9700 . no C25 H25B 0.9700 . no O7 C27 1.235(13) . no O4 C23 1.04(2) . no O4 C22 1.380(14) . no C22 C21 1.441(16) . no C22 H22A 0.9700 . no C22 H22B 0.9700 . no C21 H21A 0.9700 . no C21 H21B 0.9700 . no C28 C27 1.449(15) . no C28 H28A 0.9600 . no C28 H28B 0.9600 . no C28 H28C 0.9600 . no O5 C23 1.107(17) . no C26 H26A 0.9700 . no C26 H26B 0.9700 . no C24 C23 1.406(18) . no C24 H24A 0.9600 . no C24 H24B 0.9600 . no C24 H24C 0.9600 . no 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 C8 O3 C7 103.1(5) . . no O2 N1 O1 122.5(7) . . no O2 N1 C1 119.3(7) . . no O1 N1 C1 118.2(7) . . no C7 N2 N3 106.5(6) . . no C8 N3 N2 105.4(6) . . no N5 N4 C12 112.5(6) . . no N4 N5 C15 114.6(6) . . no C2 C1 C6 121.6(8) . . no C2 C1 N1 119.5(7) . . no C6 C1 N1 118.8(7) . . no C1 C2 C3 119.0(7) . . no C1 C2 H2 120.5 . . no C3 C2 H2 120.5 . . no C4 C3 C2 120.3(7) . . no C4 C3 H3 119.9 . . no C2 C3 H3 119.9 . . no C3 C4 C5 119.6(7) . . no C3 C4 C7 121.7(6) . . no C5 C4 C7 118.7(6) . . no C6 C5 C4 120.9(7) . . no C6 C5 H5 119.6 . . no C4 C5 H5 119.6 . . no C5 C6 C1 118.6(7) . . no C5 C6 H6 120.7 . . no C1 C6 H6 120.7 . . no N2 C7 O3 111.5(7) . . no N2 C7 C4 126.4(6) . . no O3 C7 C4 122.0(6) . . no N3 C8 O3 113.4(6) . . no N3 C8 C9 127.4(7) . . no O3 C8 C9 119.2(6) . . no C10 C9 C14 118.4(7) . . no C10 C9 C8 123.2(7) . . no C14 C9 C8 118.4(6) . . no C11 C10 C9 121.9(7) . . no C11 C10 H10 119.1 . . no C9 C10 H10 119.1 . . no C10 C11 C12 119.8(7) . . no C10 C11 H11 120.1 . . no C12 C11 H11 120.1 . . no C11 C12 C13 119.3(7) . . no C11 C12 N4 123.9(7) . . no C13 C12 N4 116.8(7) . . no C14 C13 C12 121.0(7) . . no C14 C13 H13 119.5 . . no C12 C13 H13 119.5 . . no C13 C14 C9 119.7(6) . . no C13 C14 H14 120.2 . . no C9 C14 H14 120.2 . . no C20 C15 C16 119.1(7) . . no C20 C15 N5 125.9(7) . . no C16 C15 N5 114.8(6) . . no C17 C16 C15 119.9(7) . . no C17 C16 H16 120.0 . . no C15 C16 H16 120.0 . . no C16 C17 C18 121.7(7) . . no C16 C17 H17 119.1 . . no C18 C17 H17 119.1 . . no N6 C18 C19 122.6(8) . . no N6 C18 C17 120.5(8) . . no C19 C18 C17 116.8(7) . . no C20 C19 C18 121.0(8) . . no C20 C19 H19 119.5 . . no C18 C19 H19 119.5 . . no C15 C20 C19 121.2(8) . . no C15 C20 H20 119.4 . . no C19 C20 H20 119.4 . . no C18 N6 C21 121.9(8) . . no C18 N6 C25 122.5(8) . . no C21 N6 C25 115.2(8) . . no C27 O6 C26 126.3(12) . . no C26 C25 N6 108.0(13) . . no C26 C25 H25A 110.1 . . no N6 C25 H25A 110.1 . . no C26 C25 H25B 110.1 . . no N6 C25 H25B 110.1 . . no H25A C25 H25B 108.4 . . no C23 O4 C22 143(2) . . no C23 O4 O5 41.5(11) . . no C22 O4 O5 102.1(14) . . no O4 C22 C21 109.4(12) . . no O4 C22 H22A 109.8 . . no C21 C22 H22A 109.8 . . no O4 C22 H22B 109.8 . . no C21 C22 H22B 109.8 . . no H22A C22 H22B 108.2 . . no N6 C21 C22 116.3(13) . . no N6 C21 H21A 108.2 . . no C22 C21 H21A 108.2 . . no N6 C21 H21B 108.2 . . no C22 C21 H21B 108.2 . . no H21A C21 H21B 107.4 . . no C27 C28 H28A 109.5 . . no C27 C28 H28B 109.5 . . no H28A C28 H28B 109.5 . . no C27 C28 H28C 109.5 . . no H28A C28 H28C 109.5 . . no H28B C28 H28C 109.5 . . no O7 C27 O6 117.9(15) . . no O7 C27 C28 123.3(14) . . no O6 C27 C28 118.2(13) . . no C23 O5 O4 38.7(13) . . no C25 C26 O6 103.5(13) . . no C25 C26 H26A 111.0 . . no O6 C26 H26A 111.0 . . no C25 C26 H26B 111.1 . . no O6 C26 H26B 111.0 . . no H26A C26 H26B 109.0 . . no C23 C24 H24A 109.5 . . no C23 C24 H24B 109.5 . . no H24A C24 H24B 109.5 . . no C23 C24 H24C 109.5 . . no H24A C24 H24C 109.5 . . no H24B C24 H24C 109.5 . . no O4 C23 O5 100(2) . . no O4 C23 C24 141(2) . . no O5 C23 C24 118(2) . . no 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 C16 C15 N5 N4 -174.2(7) . . . . no C15 N5 N4 C12 -174.3(6) . . . . no N5 N4 C12 C13 -158.0(7) . . . . no C14 C9 C8 O3 173.9(6) . . . . no C9 C8 O3 C7 -179.4(6) . . . . no C8 O3 C7 C4 177.5(7) . . . . no O3 C7 C4 C5 173.7(7) . . . . no _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 59.88 _diffrn_measured_fraction_theta_full 0.866 _refine_diff_density_max 0.411 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.068