# 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, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Stefan Spange' _publ_contact_author_email JEANETTE.DOERR@CHEMIE.TU-CHEMNITZ.DE _publ_section_title ; Solvatochromism and linear solvation energy relationship of diol- and proline-functionalized azo dyes using the KAMLET-TAFT and CATAL\'AN solvent parameter sets ; loop_ _publ_author_name 'Stefan Spange' 'Katja Hofmann' 'Heinrich Lang' 'Tobias Ruffer' 'Katja Schreiter' 'A Seifert' # Attachment 'B809055F.cif' data_spang28 _database_code_depnum_ccdc_archive 'CCDC 680370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N6 O9' _chemical_formula_weight 464.40 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.780(1) _cell_length_b 8.0970(8) _cell_length_c 19.7070(16) _cell_angle_alpha 95.732(8) _cell_angle_beta 96.607(9) _cell_angle_gamma 92.151(6) _cell_volume 1068.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 3662 _cell_measurement_theta_min 4.5357 _cell_measurement_theta_max 60.4712 _exptl_crystal_description plate _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_T_min 0.94860 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'oxford gemini s' _diffrn_measurement_method 'w\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% ? _diffrn_reflns_number 7626 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.54 _diffrn_reflns_theta_max 60.46 _reflns_number_total 3106 _reflns_number_gt 2310 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0631P)^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_extinction_coef ? _refine_ls_number_reflns 3106 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 C1 C 0.5635(2) -0.1970(2) -0.15076(8) 0.0249(4) Uani 1 1 d . . . C2 C 0.5772(2) -0.3025(2) -0.09936(8) 0.0249(4) Uani 1 1 d . . . H2 H 0.5379 -0.4145 -0.1085 0.030 Uiso 1 1 calc R . . C3 C 0.6515(2) -0.2345(2) -0.03406(8) 0.0232(4) Uani 1 1 d . . . C4 C 0.7141(2) -0.0663(2) -0.01873(8) 0.0233(4) Uani 1 1 d . . . C5 C 0.6991(2) 0.0340(2) -0.07244(8) 0.0247(4) Uani 1 1 d . . . H5 H 0.7404 0.1457 -0.0638 0.030 Uiso 1 1 calc R . . C6 C 0.6239(2) -0.0299(2) -0.13817(9) 0.0262(4) Uani 1 1 d . . . H6 H 0.6138 0.0381 -0.1736 0.031 Uiso 1 1 calc R . . C7 C 0.9166(2) 0.2056(2) 0.12528(8) 0.0233(4) Uani 1 1 d . . . C8 C 0.9327(2) 0.1135(2) 0.18247(8) 0.0255(4) Uani 1 1 d . . . H8 H 0.8939 0.0011 0.1767 0.031 Uiso 1 1 calc R . . C9 C 1.0046(2) 0.1874(2) 0.24607(8) 0.0273(4) Uani 1 1 d . . . H9 H 1.0105 0.1245 0.2832 0.033 Uiso 1 1 calc R . . C10 C 1.0714(2) 0.3589(2) 0.25756(8) 0.0254(4) Uani 1 1 d . . . C11 C 1.0556(2) 0.4476(2) 0.19832(8) 0.0251(4) Uani 1 1 d . . . C12 C 0.9774(2) 0.3716(2) 0.13420(8) 0.0238(4) Uani 1 1 d . . . H12 H 0.9659 0.4334 0.0967 0.029 Uiso 1 1 calc R . . C13 C 0.9506(3) 0.3663(3) 0.41120(9) 0.0410(5) Uani 1 1 d . . . H13A H 0.9278 0.4830 0.4222 0.049 Uiso 1 1 calc R . . H13B H 0.8462 0.3204 0.3758 0.049 Uiso 1 1 calc R . . C14 C 1.1510(3) 0.3502(2) 0.38407(9) 0.0358(5) Uani 1 1 d . . . H14 H 1.1758 0.2321 0.3749 0.043 Uiso 1 1 calc R . . C15 C 1.3234(3) 0.4346(3) 0.43313(10) 0.0456(5) Uani 1 1 d . . . H15A H 1.3180 0.3990 0.4785 0.055 Uiso 1 1 calc R . . H15B H 1.4479 0.4009 0.4176 0.055 Uiso 1 1 calc R . . C16 C 0.7074(4) -0.2295(3) 0.31866(14) 0.0729(8) Uani 1 1 d . . . H16A H 0.8362 -0.2540 0.3057 0.109 Uiso 1 1 calc R . . H16B H 0.6241 -0.1985 0.2797 0.109 Uiso 1 1 calc R . . H16C H 0.6487 -0.3261 0.3345 0.109 Uiso 1 1 calc R . . C17 C 0.7279(4) -0.0902(3) 0.37456(11) 0.0510(6) Uani 1 1 d . . . C18 C 0.5402(4) -0.0365(3) 0.40168(13) 0.0694(8) Uani 1 1 d . . . H18A H 0.5710 0.0533 0.4375 0.104 Uiso 1 1 calc R . . H18B H 0.4779 -0.1283 0.4198 0.104 Uiso 1 1 calc R . . H18C H 0.4515 -0.0002 0.3652 0.104 Uiso 1 1 calc R . . N1 N 0.4864(2) -0.26624(19) -0.22087(7) 0.0285(4) Uani 1 1 d . . . N2 N 0.6698(2) -0.34903(19) 0.01946(7) 0.0275(3) Uani 1 1 d . . . N3 N 0.79718(19) -0.01120(17) 0.04986(7) 0.0243(3) Uani 1 1 d . . . N4 N 0.83865(19) 0.14342(18) 0.05812(7) 0.0244(3) Uani 1 1 d . . . N5 N 1.1471(2) 0.4274(2) 0.32031(7) 0.0305(4) Uani 1 1 d . . . N6 N 1.1209(2) 0.62100(19) 0.20173(7) 0.0309(4) Uani 1 1 d . . . O1 O 0.43270(18) -0.41410(16) -0.23062(6) 0.0362(3) Uani 1 1 d . . . O2 O 0.48047(18) -0.17350(16) -0.26668(6) 0.0357(3) Uani 1 1 d . . . O3 O 0.61733(18) -0.30595(16) 0.07572(6) 0.0338(3) Uani 1 1 d . . . O4 O 0.73335(18) -0.48589(16) 0.00320(6) 0.0359(3) Uani 1 1 d . . . O5 O 0.9419(3) 0.2820(2) 0.47098(7) 0.0552(5) Uani 1 1 d . . . O6 O 1.3175(2) 0.61064(18) 0.43720(7) 0.0447(4) Uani 1 1 d . . . O7 O 1.1908(2) 0.69697(16) 0.25747(6) 0.0389(3) Uani 1 1 d . . . O8 O 1.1035(2) 0.68971(17) 0.14878(7) 0.0513(4) Uani 1 1 d . . . O9 O 0.8900(3) -0.0229(2) 0.39564(8) 0.0622(5) Uani 1 1 d . . . H5N H 1.180(3) 0.529(3) 0.3233(10) 0.039(6) Uiso 1 1 d . . . H5O H 0.926(4) 0.171(4) 0.4557(14) 0.083(9) Uiso 1 1 d . . . H6O H 1.235(4) 0.654(4) 0.4671(15) 0.087(10) Uiso 1 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 0.0187(8) 0.0300(11) 0.0250(9) -0.0015(7) 0.0034(7) -0.0018(7) C2 0.0206(8) 0.0222(10) 0.0312(10) -0.0014(7) 0.0049(7) -0.0026(6) C3 0.0196(8) 0.0237(10) 0.0265(9) 0.0022(7) 0.0046(7) -0.0005(7) C4 0.0185(8) 0.0256(10) 0.0255(9) 0.0000(7) 0.0043(7) -0.0007(7) C5 0.0231(9) 0.0216(10) 0.0292(10) 0.0012(7) 0.0051(7) -0.0040(7) C6 0.0235(9) 0.0279(11) 0.0277(9) 0.0052(7) 0.0042(7) -0.0021(7) C7 0.0189(8) 0.0266(10) 0.0241(9) 0.0004(7) 0.0043(7) -0.0009(7) C8 0.0246(9) 0.0239(10) 0.0274(9) 0.0000(7) 0.0047(7) -0.0041(7) C9 0.0274(9) 0.0292(11) 0.0255(9) 0.0046(7) 0.0038(7) -0.0046(7) C10 0.0221(8) 0.0288(10) 0.0245(9) -0.0003(7) 0.0037(7) -0.0041(7) C11 0.0239(9) 0.0221(10) 0.0289(10) -0.0003(7) 0.0062(7) -0.0040(7) C12 0.0230(8) 0.0238(10) 0.0252(9) 0.0042(7) 0.0045(7) -0.0011(7) C13 0.0575(13) 0.0364(12) 0.0271(10) -0.0021(8) 0.0074(9) -0.0173(9) C14 0.0482(11) 0.0326(12) 0.0241(10) 0.0024(8) -0.0020(8) -0.0096(9) C15 0.0591(14) 0.0406(14) 0.0327(11) 0.0048(9) -0.0085(9) -0.0160(10) C16 0.0580(15) 0.0581(18) 0.092(2) -0.0290(14) -0.0026(14) -0.0012(12) C17 0.0710(16) 0.0292(13) 0.0520(13) 0.0012(9) 0.0104(12) -0.0105(11) C18 0.096(2) 0.0475(16) 0.0723(17) 0.0091(12) 0.0440(15) -0.0079(13) N1 0.0243(8) 0.0340(10) 0.0259(8) -0.0010(7) 0.0030(6) -0.0045(6) N2 0.0280(8) 0.0238(9) 0.0286(8) 0.0009(6) -0.0021(6) -0.0062(6) N3 0.0225(7) 0.0240(9) 0.0255(8) -0.0002(6) 0.0036(6) -0.0044(6) N4 0.0226(7) 0.0231(9) 0.0264(8) -0.0008(6) 0.0030(6) -0.0039(6) N5 0.0368(9) 0.0273(10) 0.0255(8) 0.0006(6) 0.0021(6) -0.0099(7) N6 0.0350(8) 0.0274(9) 0.0291(9) -0.0012(7) 0.0046(7) -0.0065(7) O1 0.0401(7) 0.0318(8) 0.0333(7) -0.0058(5) 0.0011(6) -0.0100(6) O2 0.0395(7) 0.0415(9) 0.0248(7) 0.0040(6) 0.0010(5) -0.0064(6) O3 0.0428(8) 0.0316(8) 0.0267(7) 0.0027(5) 0.0056(6) -0.0069(5) O4 0.0435(8) 0.0252(8) 0.0371(7) 0.0010(6) -0.0019(6) 0.0048(6) O5 0.0960(13) 0.0373(10) 0.0312(8) -0.0022(6) 0.0179(7) -0.0280(8) O6 0.0574(9) 0.0403(9) 0.0323(8) 0.0000(6) -0.0017(7) -0.0205(7) O7 0.0528(8) 0.0302(8) 0.0296(7) -0.0042(6) -0.0010(6) -0.0144(6) O8 0.0868(11) 0.0330(9) 0.0313(8) 0.0075(6) -0.0003(7) -0.0214(7) O9 0.0785(12) 0.0427(10) 0.0611(10) -0.0069(7) 0.0089(9) -0.0207(9) _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 1.386(2) . ? C1 C6 1.389(2) . ? C1 N1 1.468(2) . ? C2 C3 1.379(2) . ? C2 H2 0.9300 . ? C3 C4 1.404(2) . ? C3 N2 1.470(2) . ? C4 C5 1.394(2) . ? C4 N3 1.424(2) . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.379(2) . ? C7 N4 1.404(2) . ? C7 C8 1.409(2) . ? C8 C9 1.362(2) . ? C8 H8 0.9300 . ? C9 C10 1.432(2) . ? C9 H9 0.9300 . ? C10 N5 1.340(2) . ? C10 C11 1.427(2) . ? C11 C12 1.386(2) . ? C11 N6 1.449(2) . ? C12 H12 0.9300 . ? C13 O5 1.425(2) . ? C13 C14 1.522(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N5 1.456(2) . ? C14 C15 1.522(3) . ? C14 H14 0.9800 . ? C15 O6 1.422(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.487(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O9 1.217(3) . ? C17 C18 1.498(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 O1 1.2280(19) . ? N1 O2 1.2288(19) . ? N2 O3 1.2248(18) . ? N2 O4 1.2300(18) . ? N3 N4 1.2631(19) . ? N5 H5N 0.84(2) . ? N6 O8 1.227(2) . ? N6 O7 1.2382(19) . ? O5 H5O 0.92(3) . ? O6 H6O 0.91(3) . ? 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 C1 C6 122.14(15) . . ? C2 C1 N1 118.46(15) . . ? C6 C1 N1 119.39(15) . . ? C3 C2 C1 117.29(16) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C3 C4 122.68(15) . . ? C2 C3 N2 116.55(15) . . ? C4 C3 N2 120.73(14) . . ? C5 C4 C3 117.69(15) . . ? C5 C4 N3 124.35(15) . . ? C3 C4 N3 117.89(15) . . ? C6 C5 C4 121.03(16) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 119.16(16) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C12 C7 N4 115.49(15) . . ? C12 C7 C8 119.18(15) . . ? N4 C7 C8 125.31(15) . . ? C9 C8 C7 120.66(16) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 122.02(16) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? N5 C10 C11 123.36(16) . . ? N5 C10 C9 120.88(16) . . ? C11 C10 C9 115.75(15) . . ? C12 C11 C10 121.51(16) . . ? C12 C11 N6 116.48(15) . . ? C10 C11 N6 122.01(14) . . ? C7 C12 C11 120.84(16) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? O5 C13 C14 111.53(18) . . ? O5 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? O5 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N5 C14 C13 109.36(16) . . ? N5 C14 C15 107.01(15) . . ? C13 C14 C15 113.48(16) . . ? N5 C14 H14 109.0 . . ? C13 C14 H14 109.0 . . ? C15 C14 H14 109.0 . . ? O6 C15 C14 111.51(17) . . ? O6 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? O6 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O9 C17 C16 120.7(2) . . ? O9 C17 C18 122.7(2) . . ? C16 C17 C18 116.6(2) . . ? 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 . . ? O1 N1 O2 123.58(14) . . ? O1 N1 C1 118.17(14) . . ? O2 N1 C1 118.25(14) . . ? O3 N2 O4 124.34(15) . . ? O3 N2 C3 119.29(14) . . ? O4 N2 C3 116.33(14) . . ? N4 N3 C4 112.04(13) . . ? N3 N4 C7 114.61(14) . . ? C10 N5 C14 126.53(16) . . ? C10 N5 H5N 115.3(14) . . ? C14 N5 H5N 117.5(14) . . ? O8 N6 O7 121.43(15) . . ? O8 N6 C11 118.66(14) . . ? O7 N6 C11 119.91(14) . . ? C13 O5 H5O 106.0(17) . . ? C15 O6 H6O 113.8(19) . . ? 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 C1 C2 C3 0.9(2) . . . . ? N1 C1 C2 C3 179.54(14) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C1 C2 C3 N2 -178.49(14) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? N2 C3 C4 C5 177.75(14) . . . . ? C2 C3 C4 N3 -177.08(14) . . . . ? N2 C3 C4 N3 0.6(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? N3 C4 C5 C6 177.42(14) . . . . ? C4 C5 C6 C1 -0.3(2) . . . . ? C2 C1 C6 C5 -0.3(2) . . . . ? N1 C1 C6 C5 -179.02(14) . . . . ? C12 C7 C8 C9 1.0(2) . . . . ? N4 C7 C8 C9 -177.74(15) . . . . ? C7 C8 C9 C10 -1.7(3) . . . . ? C8 C9 C10 N5 -177.96(16) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? N5 C10 C11 C12 179.58(15) . . . . ? C9 C10 C11 C12 0.9(2) . . . . ? N5 C10 C11 N6 -0.1(3) . . . . ? C9 C10 C11 N6 -178.79(14) . . . . ? N4 C7 C12 C11 179.51(14) . . . . ? C8 C7 C12 C11 0.7(2) . . . . ? C10 C11 C12 C7 -1.6(2) . . . . ? N6 C11 C12 C7 178.10(14) . . . . ? O5 C13 C14 N5 175.74(15) . . . . ? O5 C13 C14 C15 -64.9(2) . . . . ? N5 C14 C15 O6 50.0(2) . . . . ? C13 C14 C15 O6 -70.7(2) . . . . ? C2 C1 N1 O1 1.8(2) . . . . ? C6 C1 N1 O1 -179.52(14) . . . . ? C2 C1 N1 O2 -177.71(14) . . . . ? C6 C1 N1 O2 1.0(2) . . . . ? C2 C3 N2 O3 -136.36(15) . . . . ? C4 C3 N2 O3 45.8(2) . . . . ? C2 C3 N2 O4 41.73(19) . . . . ? C4 C3 N2 O4 -136.09(15) . . . . ? C5 C4 N3 N4 6.3(2) . . . . ? C3 C4 N3 N4 -176.73(13) . . . . ? C4 N3 N4 C7 178.51(12) . . . . ? C12 C7 N4 N3 175.10(13) . . . . ? C8 C7 N4 N3 -6.1(2) . . . . ? C11 C10 N5 C14 173.76(17) . . . . ? C9 C10 N5 C14 -7.7(3) . . . . ? C13 C14 N5 C10 -81.7(2) . . . . ? C15 C14 N5 C10 155.05(18) . . . . ? C12 C11 N6 O8 0.1(2) . . . . ? C10 C11 N6 O8 179.80(16) . . . . ? C12 C11 N6 O7 179.45(15) . . . . ? C10 C11 N6 O7 -0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 60.46 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.192 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.043