# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name K.Hofmann S.Brumm C.Mende I.Roth K.Nagel D.Schaarschmidt H.Lang S.Spange _publ_contact_author_name 'Dieter Schaarschmidt' _publ_contact_author_email dieter.schaarschmidt@chemie.tu-chemnitz.de data_exp_049 _database_code_depnum_ccdc_archive 'CCDC 843228' #TrackingRef '- exp_049.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N6 O6' _chemical_formula_sum 'C15 H14 N6 O6' _chemical_formula_weight 374.32 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 monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 13.8296(5) _cell_length_b 6.6323(2) _cell_length_c 35.6388(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.160(3) _cell_angle_gamma 90.00 _cell_volume 3268.85(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7629 _cell_measurement_theta_min 3.7232 _cell_measurement_theta_max 66.7321 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82244 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) 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_% 0 _diffrn_reflns_number 10647 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 62.49 _reflns_number_total 3970 _reflns_number_gt 3544 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _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. Some difficulties have been encountered in the determination of the crystal system and space group. In particular, the question was raised whether this compound crystallized in an orthorhombic or monoclinic lattice. While the beta angle significantly deviated from 90 deg, the comparison of symmetry equivalent reflections suggested the Laue symmetry mmm. Space group determination after integration in an orthorhombic lattice resulted in centrosymmetric Cmca or non-centrosymmetric Aba2 due to the systematic absence of reflections. In Cmca no reasonable solution was found. In contrast, using Aba2 a solution was obtained with one molecule in the asymmetric unit statistically disordered (ratio 0.51:0.49) on two positions (parallel orientation). However, the resulting structural parameters: R1 0.2195, wR2 0.5128, GOF 2.91, residual electron density 0.57 and -1.22, absolute structure parameter 0.2(9) indicate that Aba2 is the wrong space group and hence orthorhombic is the wrong lattice. Space group determination ; _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^)+(0.0504P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.34(13) _refine_ls_number_reflns 3970 _refine_ls_number_parameters 495 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0683 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.002 _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 0.63923(14) 0.4907(3) 0.95344(5) 0.0228(4) Uani 1 1 d . . . H1 H 0.5982 0.4108 0.9366 0.027 Uiso 1 1 calc R . . C2 C 0.65136(16) 0.3763(4) 0.99005(6) 0.0317(5) Uani 1 1 d . . . H2A H 0.6808 0.2479 0.9852 0.048 Uiso 1 1 calc R . . H2B H 0.5892 0.3560 1.0013 0.048 Uiso 1 1 calc R . . H2C H 0.6917 0.4526 1.0068 0.048 Uiso 1 1 calc R . . C3 C 0.59311(15) 0.6956(4) 0.95870(6) 0.0285(5) Uani 1 1 d . . . H3A H 0.5872 0.7614 0.9348 0.043 Uiso 1 1 calc R . . H3B H 0.6327 0.7759 0.9750 0.043 Uiso 1 1 calc R . . H3C H 0.5301 0.6795 0.9696 0.043 Uiso 1 1 calc R . . C4 C 0.75264(13) 0.5318(3) 0.89945(5) 0.0184(4) Uani 1 1 d . . . C5 C 0.84786(12) 0.5595(3) 0.88395(5) 0.0180(4) Uani 1 1 d . . . C6 C 0.86253(12) 0.5709(3) 0.84557(5) 0.0183(4) Uani 1 1 d . . . H6 H 0.9249 0.5888 0.8364 0.022 Uiso 1 1 calc R . . C7 C 0.78628(12) 0.5560(3) 0.82064(4) 0.0170(4) Uani 1 1 d . . . C8 C 0.69150(13) 0.5315(3) 0.83496(5) 0.0189(4) Uani 1 1 d . . . H8 H 0.6395 0.5218 0.8185 0.023 Uiso 1 1 calc R . . C9 C 0.67582(12) 0.5222(3) 0.87264(5) 0.0187(4) Uani 1 1 d . . . H9 H 0.6127 0.5089 0.8812 0.022 Uiso 1 1 calc R . . C10 C 0.77164(12) 0.5554(3) 0.72192(5) 0.0170(4) Uani 1 1 d . . . C11 C 0.86772(12) 0.5694(3) 0.70982(5) 0.0190(4) Uani 1 1 d . . . H11 H 0.9176 0.5783 0.7273 0.023 Uiso 1 1 calc R . . C12 C 0.88826(12) 0.5700(3) 0.67190(5) 0.0190(4) Uani 1 1 d . . . H12 H 0.9518 0.5823 0.6637 0.023 Uiso 1 1 calc R . . C13 C 0.81343(12) 0.5522(3) 0.64607(5) 0.0180(4) Uani 1 1 d . . . C14 C 0.71757(12) 0.5361(3) 0.65685(5) 0.0183(4) Uani 1 1 d . . . H14 H 0.6680 0.5226 0.6393 0.022 Uiso 1 1 calc R . . C15 C 0.69924(12) 0.5411(3) 0.69496(5) 0.0167(4) Uani 1 1 d . . . C16 C 0.63943(14) 0.9904(3) 0.54663(5) 0.0226(4) Uani 1 1 d . . . H16 H 0.5986 0.9104 0.5634 0.027 Uiso 1 1 calc R . . C17 C 0.65128(16) 0.8760(4) 0.51001(6) 0.0317(5) Uani 1 1 d . . . H17A H 0.6809 0.7477 0.5149 0.048 Uiso 1 1 calc R . . H17B H 0.6915 0.9524 0.4933 0.048 Uiso 1 1 calc R . . H17C H 0.5890 0.8556 0.4987 0.048 Uiso 1 1 calc R . . C18 C 0.59304(15) 1.1960(4) 0.54138(6) 0.0283(5) Uani 1 1 d . . . H18A H 0.5873 1.2616 0.5653 0.042 Uiso 1 1 calc R . . H18B H 0.5300 1.1799 0.5305 0.042 Uiso 1 1 calc R . . H18C H 0.6325 1.2765 0.5251 0.042 Uiso 1 1 calc R . . C19 C 0.75283(13) 1.0318(3) 0.60044(5) 0.0184(4) Uani 1 1 d . . . C20 C 0.84762(12) 1.0591(3) 0.61603(5) 0.0178(4) Uani 1 1 d . . . C21 C 0.86274(12) 1.0710(3) 0.65444(5) 0.0186(4) Uani 1 1 d . . . H21 H 0.9251 1.0893 0.6636 0.022 Uiso 1 1 calc R . . C22 C 0.78631(12) 1.0559(3) 0.67943(5) 0.0171(4) Uani 1 1 d . . . C23 C 0.69159(13) 1.0318(3) 0.66500(5) 0.0184(4) Uani 1 1 d . . . H23 H 0.6397 1.0224 0.6814 0.022 Uiso 1 1 calc R . . C24 C 0.67558(12) 1.0222(3) 0.62743(5) 0.0194(4) Uani 1 1 d . . . H24 H 0.6124 1.0090 0.6188 0.023 Uiso 1 1 calc R . . C25 C 0.77171(12) 1.0553(3) 0.77800(5) 0.0168(4) Uani 1 1 d . . . C26 C 0.86766(13) 1.0696(3) 0.79022(5) 0.0189(4) Uani 1 1 d . . . H26 H 0.9174 1.0786 0.7728 0.023 Uiso 1 1 calc R . . C27 C 0.88849(12) 1.0703(3) 0.82806(5) 0.0190(4) Uani 1 1 d . . . H27 H 0.9521 1.0824 0.8363 0.023 Uiso 1 1 calc R . . C28 C 0.81319(13) 1.0525(3) 0.85392(5) 0.0180(4) Uani 1 1 d . . . C29 C 0.71777(13) 1.0361(3) 0.84310(5) 0.0183(4) Uani 1 1 d . . . H29 H 0.6683 1.0225 0.8606 0.022 Uiso 1 1 calc R . . C30 C 0.69934(12) 1.0408(3) 0.80516(5) 0.0171(4) Uani 1 1 d . . . N1 N 0.73525(12) 0.5126(3) 0.93614(4) 0.0208(4) Uani 1 1 d . . . N2 N 0.93287(10) 0.5773(3) 0.90738(4) 0.0207(3) Uani 1 1 d . . . N3 N 0.81138(10) 0.5685(3) 0.78257(4) 0.0181(3) Uani 1 1 d . . . N4 N 0.74171(10) 0.5462(3) 0.76018(4) 0.0183(3) Uani 1 1 d . . . N5 N 0.83556(11) 0.5489(3) 0.60573(4) 0.0211(3) Uani 1 1 d . . . N6 N 0.59736(11) 0.5318(3) 0.70681(4) 0.0194(3) Uani 1 1 d . . . N7 N 0.73517(12) 1.0121(3) 0.56392(4) 0.0205(4) Uani 1 1 d . . . N8 N 0.93302(11) 1.0775(3) 0.59260(4) 0.0209(3) Uani 1 1 d . . . N9 N 0.81142(10) 1.0689(3) 0.71735(4) 0.0184(3) Uani 1 1 d . . . N10 N 0.74174(10) 1.0457(3) 0.73995(4) 0.0182(3) Uani 1 1 d . . . N11 N 0.83560(11) 1.0491(3) 0.89426(4) 0.0211(3) Uani 1 1 d . . . N12 N 0.59736(11) 1.0313(3) 0.79314(4) 0.0198(3) Uani 1 1 d . . . O1 O 0.92437(9) 0.5654(3) 0.94189(3) 0.0270(3) Uani 1 1 d . . . O2 O 1.01182(9) 0.6053(3) 0.89222(4) 0.0302(4) Uani 1 1 d . . . O3 O 0.92054(9) 0.5629(3) 0.59636(3) 0.0325(4) Uani 1 1 d . . . O4 O 0.76859(10) 0.5319(3) 0.58371(3) 0.0295(3) Uani 1 1 d . . . O5 O 0.56385(11) 0.6760(3) 0.72299(5) 0.0393(4) Uani 1 1 d . . . O6 O 0.55208(10) 0.3791(2) 0.69888(4) 0.0291(3) Uani 1 1 d . . . O7 O 0.92445(9) 1.0653(3) 0.55814(3) 0.0272(3) Uani 1 1 d . . . O8 O 1.01176(9) 1.1052(3) 0.60776(4) 0.0301(4) Uani 1 1 d . . . O9 O 0.92055(9) 1.0631(3) 0.90362(3) 0.0328(4) Uani 1 1 d . . . O10 O 0.76857(10) 1.0319(3) 0.91628(3) 0.0296(3) Uani 1 1 d . . . O11 O 0.55211(10) 0.8792(2) 0.80110(4) 0.0289(3) Uani 1 1 d . . . O12 O 0.56380(11) 1.1763(3) 0.77700(5) 0.0396(4) Uani 1 1 d . . . H1N H 0.7813(17) 0.523(4) 0.9497(6) 0.016(5) Uiso 1 1 d . . . H7N H 0.7797(18) 1.013(4) 0.5496(6) 0.024(6) 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 0.0188(9) 0.0304(13) 0.0192(9) 0.0016(8) 0.0012(7) -0.0021(8) C2 0.0281(11) 0.0425(13) 0.0246(10) 0.0076(10) 0.0022(8) -0.0011(10) C3 0.0207(10) 0.0390(14) 0.0259(10) -0.0010(9) 0.0028(7) 0.0020(10) C4 0.0202(8) 0.0147(9) 0.0204(8) -0.0010(8) 0.0006(6) 0.0020(8) C5 0.0170(8) 0.0150(9) 0.0221(8) -0.0022(9) -0.0008(6) 0.0041(9) C6 0.0170(8) 0.0144(10) 0.0234(8) -0.0014(9) 0.0032(6) 0.0019(9) C7 0.0215(8) 0.0113(9) 0.0183(8) 0.0000(8) 0.0006(6) 0.0023(9) C8 0.0192(8) 0.0153(10) 0.0220(8) -0.0006(8) -0.0027(6) 0.0013(9) C9 0.0160(8) 0.0177(10) 0.0222(9) -0.0003(8) 0.0025(6) 0.0012(8) C10 0.0198(8) 0.0108(9) 0.0204(8) -0.0002(8) 0.0020(6) -0.0019(9) C11 0.0187(8) 0.0149(10) 0.0233(8) -0.0003(9) -0.0029(6) -0.0016(9) C12 0.0176(8) 0.0154(10) 0.0241(8) -0.0003(9) 0.0044(6) -0.0020(9) C13 0.0239(9) 0.0122(9) 0.0178(8) 0.0008(8) 0.0030(6) -0.0005(9) C14 0.0195(8) 0.0136(9) 0.0218(8) 0.0001(8) -0.0033(6) 0.0024(9) C15 0.0151(8) 0.0123(9) 0.0228(8) -0.0012(8) 0.0013(6) -0.0002(9) C16 0.0193(9) 0.0302(13) 0.0184(9) -0.0021(8) -0.0003(7) -0.0017(8) C17 0.0282(11) 0.0420(13) 0.0250(10) -0.0087(10) -0.0029(8) -0.0012(10) C18 0.0206(10) 0.0384(14) 0.0259(10) 0.0018(9) -0.0016(7) 0.0011(10) C19 0.0204(8) 0.0151(9) 0.0195(8) 0.0007(8) 0.0000(6) 0.0035(9) C20 0.0167(8) 0.0163(9) 0.0204(8) 0.0019(9) 0.0017(6) 0.0038(9) C21 0.0172(8) 0.0158(10) 0.0229(8) 0.0014(9) -0.0035(6) 0.0017(9) C22 0.0198(8) 0.0116(9) 0.0198(8) 0.0010(9) 0.0003(6) 0.0014(9) C23 0.0196(8) 0.0145(9) 0.0212(9) 0.0005(8) 0.0036(6) 0.0006(9) C24 0.0152(8) 0.0194(10) 0.0235(9) -0.0001(8) -0.0021(6) 0.0008(8) C25 0.0206(8) 0.0096(9) 0.0202(8) 0.0015(8) -0.0004(6) -0.0016(9) C26 0.0190(8) 0.0156(10) 0.0220(8) 0.0008(9) 0.0030(6) -0.0038(9) C27 0.0169(8) 0.0152(10) 0.0250(9) 0.0003(9) -0.0040(6) -0.0018(9) C28 0.0232(9) 0.0128(9) 0.0180(8) 0.0004(9) -0.0019(6) -0.0016(9) C29 0.0198(8) 0.0132(9) 0.0219(8) 0.0009(8) 0.0041(6) 0.0019(9) C30 0.0150(8) 0.0136(9) 0.0228(8) 0.0001(8) -0.0012(6) -0.0007(9) N1 0.0180(8) 0.0270(10) 0.0174(7) -0.0011(7) -0.0011(6) 0.0008(7) N2 0.0170(7) 0.0247(9) 0.0204(7) -0.0025(8) -0.0002(5) 0.0032(8) N3 0.0201(7) 0.0151(8) 0.0190(7) 0.0000(7) -0.0004(5) 0.0018(7) N4 0.0220(7) 0.0153(8) 0.0176(7) -0.0012(7) 0.0010(5) -0.0017(8) N5 0.0254(8) 0.0179(9) 0.0200(7) -0.0011(8) 0.0015(6) -0.0002(8) N6 0.0179(7) 0.0214(9) 0.0190(7) 0.0014(7) -0.0008(5) 0.0003(8) N7 0.0180(8) 0.0252(10) 0.0183(7) -0.0009(7) 0.0020(6) 0.0014(7) N8 0.0177(7) 0.0236(9) 0.0215(8) 0.0028(8) 0.0000(5) 0.0031(8) N9 0.0193(7) 0.0165(8) 0.0194(7) 0.0014(7) 0.0002(5) 0.0020(7) N10 0.0209(7) 0.0157(8) 0.0181(7) 0.0003(7) -0.0007(5) -0.0021(8) N11 0.0258(8) 0.0179(9) 0.0196(7) 0.0012(8) -0.0020(6) -0.0001(8) N12 0.0173(7) 0.0238(9) 0.0184(7) -0.0021(7) 0.0005(5) -0.0003(8) O1 0.0211(6) 0.0408(9) 0.0192(6) -0.0015(7) -0.0012(4) 0.0033(8) O2 0.0159(6) 0.0486(11) 0.0262(7) -0.0028(7) 0.0015(5) -0.0016(7) O3 0.0255(7) 0.0471(10) 0.0250(6) -0.0007(8) 0.0086(5) -0.0043(8) O4 0.0312(7) 0.0392(9) 0.0183(6) -0.0007(7) -0.0028(5) -0.0026(8) O5 0.0224(7) 0.0396(10) 0.0559(10) -0.0238(9) 0.0092(7) -0.0014(8) O6 0.0200(7) 0.0234(8) 0.0440(9) -0.0001(7) -0.0007(6) -0.0041(7) O7 0.0220(6) 0.0420(9) 0.0177(6) 0.0028(7) 0.0018(4) 0.0036(8) O8 0.0159(6) 0.0484(11) 0.0259(7) 0.0031(7) -0.0020(5) -0.0009(7) O9 0.0252(7) 0.0476(10) 0.0255(6) 0.0006(8) -0.0088(5) -0.0047(8) O10 0.0307(7) 0.0401(9) 0.0181(6) 0.0010(7) 0.0025(5) -0.0018(8) O11 0.0195(7) 0.0243(8) 0.0428(9) -0.0003(7) 0.0001(6) -0.0049(7) O12 0.0228(7) 0.0387(10) 0.0573(10) 0.0239(9) -0.0091(7) -0.0014(8) _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 N1 1.473(2) . ? C1 C3 1.513(3) . ? C1 C2 1.518(3) . ? C1 H1 0.9800 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 N1 1.337(2) . ? C4 C9 1.428(3) . ? C4 C5 1.441(2) . ? C5 C6 1.385(2) . ? C5 N2 1.445(2) . ? C6 C7 1.381(3) . ? C6 H6 0.9300 . ? C7 N3 1.404(2) . ? C7 C8 1.417(2) . ? C8 C9 1.362(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.389(2) . ? C10 C11 1.401(2) . ? C10 N4 1.427(2) . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.388(3) . ? C12 H12 0.9300 . ? C13 C14 1.385(2) . ? C13 N5 1.471(2) . ? C14 C15 1.383(3) . ? C14 H14 0.9300 . ? C15 N6 1.473(2) . ? C16 N7 1.466(3) . ? C16 C18 1.518(3) . ? C16 C17 1.519(3) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.330(3) . ? C19 C20 1.434(3) . ? C19 C24 1.441(2) . ? C20 C21 1.386(3) . ? C20 N8 1.454(2) . ? C21 C22 1.388(2) . ? C21 H21 0.9300 . ? C22 N9 1.397(2) . ? C22 C23 1.415(3) . ? C23 C24 1.358(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.398(2) . ? C25 C26 1.399(3) . ? C25 N10 1.418(2) . ? C26 C27 1.378(3) . ? C26 H26 0.9300 . ? C27 C28 1.397(2) . ? C27 H27 0.9300 . ? C28 C29 1.378(3) . ? C28 N11 1.470(2) . ? C29 C30 1.376(3) . ? C29 H29 0.9300 . ? C30 N12 1.474(2) . ? N1 H1N 0.80(3) . ? N2 O2 1.234(2) . ? N2 O1 1.238(2) . ? N3 N4 1.258(2) . ? N5 O4 1.217(2) . ? N5 O3 1.226(2) . ? N6 O5 1.210(2) . ? N6 O6 1.223(2) . ? N7 H7N 0.80(2) . ? N8 O8 1.228(2) . ? N8 O7 1.236(2) . ? N9 N10 1.267(2) . ? N11 O10 1.222(2) . ? N11 O9 1.224(2) . ? N12 O12 1.213(3) . ? N12 O11 1.221(2) . ? 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 N1 C1 C3 110.11(17) . . ? N1 C1 C2 108.16(16) . . ? C3 C1 C2 112.83(17) . . ? N1 C1 H1 108.5 . . ? C3 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C9 120.98(16) . . ? N1 C4 C5 123.65(16) . . ? C9 C4 C5 115.36(15) . . ? C6 C5 C4 121.45(16) . . ? C6 C5 N2 116.42(14) . . ? C4 C5 N2 122.13(15) . . ? C7 C6 C5 121.20(15) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 N3 115.30(15) . . ? C6 C7 C8 118.80(15) . . ? N3 C7 C8 125.89(15) . . ? C9 C8 C7 120.68(16) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C4 122.48(16) . . ? C8 C9 H9 118.8 . . ? C4 C9 H9 118.8 . . ? C15 C10 C11 118.30(15) . . ? C15 C10 N4 116.58(14) . . ? C11 C10 N4 125.07(16) . . ? C12 C11 C10 119.93(16) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.56(15) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 122.35(15) . . ? C14 C13 N5 118.13(15) . . ? C12 C13 N5 119.52(15) . . ? C15 C14 C13 116.65(16) . . ? C15 C14 H14 121.7 . . ? C13 C14 H14 121.7 . . ? C14 C15 C10 123.18(15) . . ? C14 C15 N6 117.29(15) . . ? C10 C15 N6 119.53(14) . . ? N7 C16 C18 110.16(17) . . ? N7 C16 C17 108.10(16) . . ? C18 C16 C17 112.92(17) . . ? N7 C16 H16 108.5 . . ? C18 C16 H16 108.5 . . ? C17 C16 H16 108.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 C20 123.83(16) . . ? N7 C19 C24 120.96(16) . . ? C20 C19 C24 115.19(16) . . ? C21 C20 C19 121.67(15) . . ? C21 C20 N8 116.23(15) . . ? C19 C20 N8 122.10(15) . . ? C20 C21 C22 121.10(16) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 N9 115.39(15) . . ? C21 C22 C23 118.74(16) . . ? N9 C22 C23 125.87(15) . . ? C24 C23 C22 120.80(16) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C19 122.47(16) . . ? C23 C24 H24 118.8 . . ? C19 C24 H24 118.8 . . ? C30 C25 C26 117.99(16) . . ? C30 C25 N10 116.83(15) . . ? C26 C25 N10 125.12(15) . . ? C27 C26 C25 120.04(15) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 119.39(16) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C29 C28 C27 122.48(16) . . ? C29 C28 N11 118.13(15) . . ? C27 C28 N11 119.39(15) . . ? C30 C29 C28 116.60(16) . . ? C30 C29 H29 121.7 . . ? C28 C29 H29 121.7 . . ? C29 C30 C25 123.47(16) . . ? C29 C30 N12 117.32(15) . . ? C25 C30 N12 119.22(15) . . ? C4 N1 C1 125.72(16) . . ? C4 N1 H1N 116.0(15) . . ? C1 N1 H1N 118.1(14) . . ? O2 N2 O1 122.07(15) . . ? O2 N2 C5 118.62(14) . . ? O1 N2 C5 119.31(14) . . ? N4 N3 C7 114.52(14) . . ? N3 N4 C10 112.17(14) . . ? O4 N5 O3 124.01(14) . . ? O4 N5 C13 118.14(14) . . ? O3 N5 C13 117.85(15) . . ? O5 N6 O6 124.60(15) . . ? O5 N6 C15 118.13(17) . . ? O6 N6 C15 117.26(16) . . ? C19 N7 C16 125.74(15) . . ? C19 N7 H7N 118.9(17) . . ? C16 N7 H7N 115.3(17) . . ? O8 N8 O7 121.96(14) . . ? O8 N8 C20 118.73(15) . . ? O7 N8 C20 119.31(15) . . ? N10 N9 C22 114.82(14) . . ? N9 N10 C25 112.42(14) . . ? O10 N11 O9 124.17(15) . . ? O10 N11 C28 118.13(15) . . ? O9 N11 C28 117.70(14) . . ? O12 N12 O11 124.75(15) . . ? O12 N12 C30 117.92(17) . . ? O11 N12 C30 117.30(17) . . ? 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 N1 C4 C5 C6 177.5(2) . . . . ? C9 C4 C5 C6 -1.4(3) . . . . ? N1 C4 C5 N2 -2.7(3) . . . . ? C9 C4 C5 N2 178.4(2) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? N2 C5 C6 C7 -179.90(19) . . . . ? C5 C6 C7 N3 -179.55(19) . . . . ? C5 C6 C7 C8 0.9(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? N3 C7 C8 C9 -179.7(2) . . . . ? C7 C8 C9 C4 -1.3(3) . . . . ? N1 C4 C9 C8 -176.8(2) . . . . ? C5 C4 C9 C8 2.1(3) . . . . ? C15 C10 C11 C12 0.4(3) . . . . ? N4 C10 C11 C12 177.7(2) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C11 C12 C13 N5 -178.80(19) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? N5 C13 C14 C15 -179.60(19) . . . . ? C13 C14 C15 C10 -1.8(3) . . . . ? C13 C14 C15 N6 177.77(17) . . . . ? C11 C10 C15 C14 1.3(3) . . . . ? N4 C10 C15 C14 -176.23(19) . . . . ? C11 C10 C15 N6 -178.34(18) . . . . ? N4 C10 C15 N6 4.2(3) . . . . ? N7 C19 C20 C21 -177.4(2) . . . . ? C24 C19 C20 C21 1.3(3) . . . . ? N7 C19 C20 N8 3.1(3) . . . . ? C24 C19 C20 N8 -178.25(19) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? N8 C20 C21 C22 179.81(18) . . . . ? C20 C21 C22 N9 179.58(19) . . . . ? C20 C21 C22 C23 -1.1(3) . . . . ? C21 C22 C23 C24 0.4(3) . . . . ? N9 C22 C23 C24 179.6(2) . . . . ? C22 C23 C24 C19 1.2(3) . . . . ? N7 C19 C24 C23 176.7(2) . . . . ? C20 C19 C24 C23 -2.0(3) . . . . ? C30 C25 C26 C27 -0.4(3) . . . . ? N10 C25 C26 C27 -177.6(2) . . . . ? C25 C26 C27 C28 1.3(3) . . . . ? C26 C27 C28 C29 -0.6(3) . . . . ? C26 C27 C28 N11 178.75(19) . . . . ? C27 C28 C29 C30 -0.9(3) . . . . ? N11 C28 C29 C30 179.69(19) . . . . ? C28 C29 C30 C25 1.9(3) . . . . ? C28 C29 C30 N12 -177.73(18) . . . . ? C26 C25 C30 C29 -1.3(3) . . . . ? N10 C25 C30 C29 176.2(2) . . . . ? C26 C25 C30 N12 178.31(19) . . . . ? N10 C25 C30 N12 -4.2(3) . . . . ? C9 C4 N1 C1 -3.3(3) . . . . ? C5 C4 N1 C1 177.9(2) . . . . ? C3 C1 N1 C4 -83.4(2) . . . . ? C2 C1 N1 C4 152.9(2) . . . . ? C6 C5 N2 O2 1.5(3) . . . . ? C4 C5 N2 O2 -178.37(19) . . . . ? C6 C5 N2 O1 -179.01(18) . . . . ? C4 C5 N2 O1 1.1(3) . . . . ? C6 C7 N3 N4 177.17(19) . . . . ? C8 C7 N3 N4 -3.3(3) . . . . ? C7 N3 N4 C10 -178.57(17) . . . . ? C15 C10 N4 N3 -177.34(19) . . . . ? C11 C10 N4 N3 5.4(3) . . . . ? C14 C13 N5 O4 -0.1(3) . . . . ? C12 C13 N5 O4 179.5(2) . . . . ? C14 C13 N5 O3 -179.9(2) . . . . ? C12 C13 N5 O3 -0.3(3) . . . . ? C14 C15 N6 O5 -115.9(2) . . . . ? C10 C15 N6 O5 63.7(3) . . . . ? C14 C15 N6 O6 62.8(2) . . . . ? C10 C15 N6 O6 -117.6(2) . . . . ? C20 C19 N7 C16 -177.9(2) . . . . ? C24 C19 N7 C16 3.5(3) . . . . ? C18 C16 N7 C19 83.0(2) . . . . ? C17 C16 N7 C19 -153.2(2) . . . . ? C21 C20 N8 O8 -1.2(3) . . . . ? C19 C20 N8 O8 178.4(2) . . . . ? C21 C20 N8 O7 178.99(18) . . . . ? C19 C20 N8 O7 -1.5(3) . . . . ? C21 C22 N9 N10 -176.89(19) . . . . ? C23 C22 N9 N10 3.9(3) . . . . ? C22 N9 N10 C25 178.51(17) . . . . ? C30 C25 N10 N9 177.07(18) . . . . ? C26 C25 N10 N9 -5.7(3) . . . . ? C29 C28 N11 O10 0.0(3) . . . . ? C27 C28 N11 O10 -179.46(19) . . . . ? C29 C28 N11 O9 179.8(2) . . . . ? C27 C28 N11 O9 0.4(3) . . . . ? C29 C30 N12 O12 115.6(2) . . . . ? C25 C30 N12 O12 -64.0(3) . . . . ? C29 C30 N12 O11 -62.5(3) . . . . ? C25 C30 N12 O11 117.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 62.49 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.158 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.048