# 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, 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 #TrackingRef 'ansc127-0m-1.cif' # SUBMISSION DETAILS _publ_contact_author_name 'Prof. Dr. Edwin Kroke' _publ_contact_author_address ; Institut f\"ur Anorganische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; _publ_contact_author_email edwin.kroke@chemie.tu-freiberg.de _publ_contact_author_fax '49(03731) 393174' _publ_contact_author_phone '49(03731) 394058' # TITLE, ABSTRACT AND AUTHOR LIST _publ_section_title ; A series of aryl-/alkyl-substituted melems ; _publ_section_abstract ; Four different tri-s-triazines were synthesized bearing one, two or three substituents NEt~2~ and/or NPh~2~ by reaction of cyameluric chloride and the corresponding amines. All compounds were characterised comprehensively including single crystal structure analysis, NMR, FT-IR and elemental analysis. ; loop_ _publ_author_name _publ_author_address A.Schwarzer ; Institut f\"ur Anorganische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; E.Kroke ; Institut f\"ur Anorganische Chemie TU Bergakademie Freiberg Leipziger Strasse 29 D-09596 Freiberg/Sachsen Germany ; data_ansc120 _database_code_depnum_ccdc_archive 'CCDC 804314' #TrackingRef 'ansc120.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Phenylamino-5,8-diethylamino-tri-s-triazin ; _chemical_name_common ; 1-Phenylamino-5,8-diethylamino-tri-s-triazin ; _chemical_formula_moiety 'C26 H30 N10, 0.5(C8 H10)' _chemical_formula_sum 'C30 H35 N10' _chemical_formula_weight 535.68 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' _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 9.3450(11) _cell_length_b 10.0610(13) _cell_length_c 14.9597(18) _cell_angle_alpha 83.288(7) _cell_angle_beta 87.451(7) _cell_angle_gamma 80.642(8) _cell_volume 1377.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2122 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.55 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 0.082 _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 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18263 _diffrn_reflns_av_R_equivalents 0.1007 _diffrn_reflns_av_sigmaI/netI 0.1171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4747 _reflns_number_gt 2405 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2007)' _computing_cell_refinement 'Bruker SMART (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0624P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4747 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1502 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _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 0.0487(3) 0.7372(3) 0.47708(18) 0.0169(7) Uani 1 1 d . . . C2 C 0.1063(3) 0.7802(3) 0.32872(18) 0.0161(7) Uani 1 1 d . . . C3 C 0.1513(3) 0.8458(3) 0.18157(18) 0.0180(7) Uani 1 1 d . . . C4 C -0.0758(3) 0.9207(3) 0.23394(17) 0.0164(7) Uani 1 1 d . . . C5 C -0.2959(3) 0.9923(3) 0.29893(18) 0.0181(7) Uani 1 1 d . . . C6 C -0.1266(3) 0.8706(3) 0.39412(18) 0.0170(7) Uani 1 1 d . . . C7 C 0.2313(3) 0.5950(3) 0.57577(17) 0.0178(7) Uani 1 1 d . . . C8 C 0.3528(3) 0.6572(3) 0.57128(18) 0.0213(7) Uani 1 1 d . . . H8 H 0.3454 0.7514 0.5521 0.026 Uiso 1 1 calc R . . C9 C 0.4857(3) 0.5817(3) 0.59492(19) 0.0246(8) Uani 1 1 d . . . H9 H 0.5700 0.6239 0.5904 0.030 Uiso 1 1 calc R . . C10 C 0.4967(3) 0.4451(3) 0.62507(18) 0.0256(8) Uani 1 1 d . . . H10 H 0.5875 0.3939 0.6430 0.031 Uiso 1 1 calc R . . C11 C 0.3740(3) 0.3840(3) 0.6288(2) 0.0305(8) Uani 1 1 d . . . H11 H 0.3807 0.2901 0.6486 0.037 Uiso 1 1 calc R . . C12 C 0.2420(3) 0.4586(3) 0.60404(19) 0.0257(8) Uani 1 1 d . . . H12 H 0.1582 0.4159 0.6065 0.031 Uiso 1 1 calc R . . C13 C -0.0054(3) 0.6821(3) 0.63728(17) 0.0169(7) Uani 1 1 d . . . C14 C -0.1174(3) 0.6072(3) 0.65030(19) 0.0225(7) Uani 1 1 d . . . H14 H -0.1405 0.5570 0.6044 0.027 Uiso 1 1 calc R . . C15 C -0.1955(3) 0.6062(3) 0.73094(19) 0.0257(8) Uani 1 1 d . . . H15 H -0.2718 0.5538 0.7410 0.031 Uiso 1 1 calc R . . C16 C -0.1633(3) 0.6811(3) 0.79723(19) 0.0247(8) Uani 1 1 d . . . H16 H -0.2173 0.6798 0.8525 0.030 Uiso 1 1 calc R . . C17 C -0.0527(3) 0.7574(3) 0.78310(19) 0.0256(8) Uani 1 1 d . . . H17 H -0.0314 0.8097 0.8283 0.031 Uiso 1 1 calc R . . C18 C 0.0269(3) 0.7575(3) 0.70281(18) 0.0232(7) Uani 1 1 d . . . H18 H 0.1036 0.8093 0.6929 0.028 Uiso 1 1 calc R . . C19 C 0.2131(3) 0.9180(3) 0.02330(18) 0.0229(8) Uani 1 1 d . . . H19A H 0.1087 0.9196 0.0137 0.027 Uiso 1 1 calc R . . H19B H 0.2687 0.8660 -0.0226 0.027 Uiso 1 1 calc R . . C20 C 0.2449(3) 1.0617(3) 0.00989(19) 0.0287(8) Uani 1 1 d . . . H20A H 0.1820 1.1166 0.0504 0.043 Uiso 1 1 calc R . . H20B H 0.2267 1.0999 -0.0526 0.043 Uiso 1 1 calc R . . H20C H 0.3467 1.0617 0.0232 0.043 Uiso 1 1 calc R . . C21 C 0.4006(3) 0.7827(3) 0.12580(19) 0.0241(8) Uani 1 1 d . . . H21A H 0.4258 0.7839 0.1893 0.029 Uiso 1 1 calc R . . H21B H 0.4654 0.8353 0.0873 0.029 Uiso 1 1 calc R . . C22 C 0.4274(3) 0.6373(3) 0.1034(2) 0.0340(9) Uani 1 1 d . . . H22A H 0.3702 0.5827 0.1449 0.051 Uiso 1 1 calc R . . H22B H 0.5307 0.6005 0.1092 0.051 Uiso 1 1 calc R . . H22C H 0.3985 0.6349 0.0415 0.051 Uiso 1 1 calc R . . C23 C -0.4819(3) 1.1167(3) 0.19869(18) 0.0228(7) Uani 1 1 d . . . H23A H -0.5885 1.1225 0.1972 0.027 Uiso 1 1 calc R . . H23B H -0.4380 1.0575 0.1531 0.027 Uiso 1 1 calc R . . C24 C -0.4425(3) 1.2569(3) 0.1747(2) 0.0295(8) Uani 1 1 d . . . H24A H -0.4838 1.3154 0.2204 0.044 Uiso 1 1 calc R . . H24B H -0.4815 1.2952 0.1158 0.044 Uiso 1 1 calc R . . H24C H -0.3367 1.2509 0.1722 0.044 Uiso 1 1 calc R . . C25 C -0.5353(3) 1.0783(3) 0.36368(18) 0.0208(7) Uani 1 1 d . . . H25A H -0.5882 1.1722 0.3548 0.025 Uiso 1 1 calc R . . H25B H -0.4805 1.0684 0.4199 0.025 Uiso 1 1 calc R . . C26 C -0.6445(3) 0.9806(3) 0.3744(2) 0.0330(8) Uani 1 1 d . . . H26A H -0.6976 0.9881 0.3185 0.049 Uiso 1 1 calc R . . H26B H -0.7130 1.0030 0.4240 0.049 Uiso 1 1 calc R . . H26C H -0.5934 0.8877 0.3876 0.049 Uiso 1 1 calc R . . N1 N 0.1450(2) 0.7155(2) 0.40865(14) 0.0185(6) Uani 1 1 d . . . N2 N 0.1975(2) 0.7720(2) 0.25861(14) 0.0180(6) Uani 1 1 d . . . N3 N 0.0179(2) 0.9167(2) 0.16484(14) 0.0185(6) Uani 1 1 d . . . N4 N -0.2100(2) 0.9864(2) 0.22362(14) 0.0184(6) Uani 1 1 d . . . N5 N -0.2586(2) 0.9407(2) 0.38371(14) 0.0187(6) Uani 1 1 d . . . N6 N -0.0838(2) 0.8132(2) 0.47467(14) 0.0176(6) Uani 1 1 d . . . N7 N -0.0324(2) 0.8582(2) 0.31909(14) 0.0163(6) Uani 1 1 d . . . N8 N 0.0895(2) 0.6730(2) 0.55863(14) 0.0176(6) Uani 1 1 d . . . N9 N 0.2497(2) 0.8485(2) 0.11289(14) 0.0197(6) Uani 1 1 d . . . N10 N -0.4321(2) 1.0561(2) 0.28772(14) 0.0183(6) Uani 1 1 d . . . C27 C 0.0731(3) 0.4538(3) 0.92191(19) 0.0265(8) Uani 1 1 d . . . C28 C -0.0446(3) 0.3984(3) 0.9611(2) 0.0317(8) Uani 1 1 d . . . H28 H -0.0764 0.3269 0.9351 0.038 Uiso 1 1 calc R . . C29 C 0.1165(3) 0.5555(3) 0.9633(2) 0.0326(9) Uani 1 1 d . . . H29 H 0.1978 0.5947 0.9391 0.039 Uiso 1 1 calc R . . C30 C 0.1457(3) 0.4063(3) 0.8374(2) 0.0358(9) Uani 1 1 d . . . H30A H 0.2109 0.4691 0.8124 0.054 Uiso 1 1 calc R . . H30B H 0.0719 0.4033 0.7934 0.054 Uiso 1 1 calc R . . H30C H 0.2016 0.3156 0.8512 0.054 Uiso 1 1 calc R . . 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(18) 0.0116(17) 0.0232(17) -0.0054(13) -0.0014(13) -0.0084(14) C2 0.0150(17) 0.0141(17) 0.0224(17) -0.0055(13) -0.0038(13) -0.0086(13) C3 0.0171(17) 0.0147(17) 0.0241(17) -0.0068(13) -0.0001(13) -0.0048(14) C4 0.0213(18) 0.0098(17) 0.0207(17) -0.0034(13) -0.0030(13) -0.0077(14) C5 0.0182(18) 0.0146(17) 0.0247(17) -0.0043(13) -0.0041(14) -0.0096(14) C6 0.0147(17) 0.0157(18) 0.0225(17) -0.0047(13) 0.0009(13) -0.0068(14) C7 0.0165(17) 0.0191(18) 0.0169(16) -0.0023(13) -0.0020(12) 0.0007(14) C8 0.0184(18) 0.0189(19) 0.0289(17) -0.0071(14) -0.0036(13) -0.0058(14) C9 0.0154(17) 0.025(2) 0.0364(19) -0.0088(15) -0.0019(14) -0.0069(15) C10 0.0214(19) 0.026(2) 0.0271(18) -0.0076(15) -0.0033(14) 0.0065(15) C11 0.026(2) 0.020(2) 0.042(2) 0.0023(15) 0.0007(15) 0.0014(16) C12 0.0188(18) 0.0196(19) 0.0391(19) -0.0022(15) 0.0016(14) -0.0059(15) C13 0.0136(16) 0.0155(18) 0.0206(16) -0.0010(13) -0.0017(12) 0.0006(13) C14 0.0194(18) 0.0211(19) 0.0286(18) -0.0051(14) -0.0064(13) -0.0045(14) C15 0.0179(18) 0.024(2) 0.0348(19) 0.0015(15) 0.0015(14) -0.0062(14) C16 0.0210(18) 0.025(2) 0.0246(17) 0.0015(15) 0.0027(13) 0.0021(15) C17 0.0255(19) 0.027(2) 0.0253(17) -0.0095(14) -0.0024(14) -0.0007(15) C18 0.0213(18) 0.0209(19) 0.0300(18) -0.0047(14) 0.0011(14) -0.0098(14) C19 0.0205(18) 0.023(2) 0.0251(17) -0.0018(14) 0.0017(13) -0.0052(15) C20 0.035(2) 0.025(2) 0.0276(17) -0.0014(14) 0.0011(14) -0.0105(16) C21 0.0167(18) 0.029(2) 0.0268(17) -0.0023(14) 0.0012(13) -0.0063(15) C22 0.024(2) 0.031(2) 0.043(2) 0.0003(16) 0.0022(15) 0.0023(16) C23 0.0155(17) 0.0241(19) 0.0268(17) -0.0025(14) -0.0019(13) 0.0032(14) C24 0.029(2) 0.023(2) 0.0321(18) 0.0027(15) 0.0052(14) 0.0023(15) C25 0.0165(17) 0.0195(18) 0.0259(17) -0.0050(13) 0.0013(13) -0.0001(14) C26 0.032(2) 0.030(2) 0.041(2) -0.0100(16) 0.0080(15) -0.0165(16) N1 0.0176(14) 0.0182(15) 0.0203(14) -0.0039(11) 0.0000(11) -0.0038(11) N2 0.0180(14) 0.0166(15) 0.0201(13) -0.0023(11) 0.0002(11) -0.0051(11) N3 0.0144(14) 0.0167(15) 0.0244(14) -0.0020(11) 0.0015(11) -0.0032(11) N4 0.0147(14) 0.0159(14) 0.0250(14) -0.0045(11) 0.0003(11) -0.0018(11) N5 0.0152(14) 0.0174(15) 0.0233(14) -0.0025(11) -0.0021(10) -0.0018(11) N6 0.0143(14) 0.0166(15) 0.0223(13) -0.0030(11) -0.0018(10) -0.0024(11) N7 0.0134(14) 0.0142(14) 0.0213(13) -0.0021(11) -0.0017(10) -0.0017(11) N8 0.0137(14) 0.0170(15) 0.0221(13) -0.0017(11) 0.0005(10) -0.0032(11) N9 0.0142(14) 0.0224(15) 0.0221(13) 0.0002(11) -0.0008(11) -0.0032(11) N10 0.0162(15) 0.0178(15) 0.0214(13) -0.0023(11) -0.0015(10) -0.0039(11) C27 0.0273(19) 0.0219(19) 0.0308(18) 0.0009(15) -0.0086(15) -0.0055(15) C28 0.039(2) 0.023(2) 0.037(2) -0.0028(16) -0.0116(16) -0.0166(17) C29 0.034(2) 0.033(2) 0.035(2) 0.0011(16) -0.0027(16) -0.0198(17) C30 0.038(2) 0.030(2) 0.040(2) -0.0029(16) -0.0039(16) -0.0061(17) _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 N6 1.345(3) . ? C1 N1 1.346(3) . ? C1 N8 1.352(3) . ? C2 N2 1.323(3) . ? C2 N1 1.328(3) . ? C2 N7 1.405(3) . ? C3 N2 1.344(3) . ? C3 N9 1.349(3) . ? C3 N3 1.350(3) . ? C4 N3 1.325(3) . ? C4 N4 1.325(3) . ? C4 N7 1.399(3) . ? C5 N10 1.338(3) . ? C5 N5 1.351(3) . ? C5 N4 1.355(3) . ? C6 N6 1.323(3) . ? C6 N5 1.323(3) . ? C6 N7 1.400(3) . ? C7 C12 1.376(4) . ? C7 C8 1.379(4) . ? C7 N8 1.443(3) . ? C8 C9 1.383(4) . ? C8 H8 0.9500 . ? C9 C10 1.384(4) . ? C9 H9 0.9500 . ? C10 C11 1.382(4) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.379(4) . ? C13 C14 1.380(4) . ? C13 N8 1.444(3) . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.384(4) . ? C15 H15 0.9500 . ? C16 C17 1.379(4) . ? C16 H16 0.9500 . ? C17 C18 1.385(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N9 1.465(3) . ? C19 C20 1.511(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N9 1.468(3) . ? C21 C22 1.517(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N10 1.461(3) . ? C23 C24 1.514(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 N10 1.470(3) . ? C25 C26 1.519(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.379(4) . ? C27 C28 1.389(4) . ? C27 C30 1.498(4) . ? C28 C29 1.378(4) 2_567 ? C28 H28 0.9500 . ? C29 C28 1.378(4) 2_567 ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 N6 C1 N1 128.4(3) . . ? N6 C1 N8 115.7(2) . . ? N1 C1 N8 115.9(3) . . ? N2 C2 N1 120.4(3) . . ? N2 C2 N7 120.1(2) . . ? N1 C2 N7 119.5(2) . . ? N2 C3 N9 116.1(3) . . ? N2 C3 N3 127.6(2) . . ? N9 C3 N3 116.3(2) . . ? N3 C4 N4 120.5(2) . . ? N3 C4 N7 120.0(3) . . ? N4 C4 N7 119.5(2) . . ? N10 C5 N5 116.8(2) . . ? N10 C5 N4 116.2(2) . . ? N5 C5 N4 127.0(3) . . ? N6 C6 N5 120.4(2) . . ? N6 C6 N7 120.3(3) . . ? N5 C6 N7 119.3(2) . . ? C12 C7 C8 120.2(3) . . ? C12 C7 N8 118.7(3) . . ? C8 C7 N8 120.9(3) . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C7 C12 C11 120.1(3) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C18 C13 C14 120.8(3) . . ? C18 C13 N8 118.2(2) . . ? C14 C13 N8 120.7(3) . . ? C13 C14 C15 119.1(3) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 119.8(3) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N9 C19 C20 113.3(2) . . ? N9 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? N9 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N9 C21 C22 112.9(2) . . ? N9 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N9 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N10 C23 C24 112.3(2) . . ? N10 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? N10 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N10 C25 C26 113.2(2) . . ? N10 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? N10 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C2 N1 C1 116.0(2) . . ? C2 N2 C3 116.2(2) . . ? C4 N3 C3 116.2(2) . . ? C4 N4 C5 116.5(2) . . ? C6 N5 C5 116.8(2) . . ? C6 N6 C1 115.7(2) . . ? C4 N7 C6 120.6(2) . . ? C4 N7 C2 119.5(2) . . ? C6 N7 C2 119.9(2) . . ? C1 N8 C7 123.7(2) . . ? C1 N8 C13 121.9(2) . . ? C7 N8 C13 114.3(2) . . ? C3 N9 C19 122.4(2) . . ? C3 N9 C21 120.7(2) . . ? C19 N9 C21 116.9(2) . . ? C5 N10 C23 120.7(2) . . ? C5 N10 C25 122.5(2) . . ? C23 N10 C25 116.6(2) . . ? C29 C27 C28 116.8(3) . . ? C29 C27 C30 122.3(3) . . ? C28 C27 C30 120.9(3) . . ? C29 C28 C27 121.7(3) 2_567 . ? C29 C28 H28 119.1 2_567 . ? C27 C28 H28 119.1 . . ? C28 C29 C27 121.5(3) 2_567 . ? C28 C29 H29 119.3 2_567 . ? C27 C29 H29 119.3 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? 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 C12 C7 C8 C9 0.3(4) . . . . ? N8 C7 C8 C9 174.9(2) . . . . ? C7 C8 C9 C10 -1.6(4) . . . . ? C8 C9 C10 C11 1.9(4) . . . . ? C9 C10 C11 C12 -0.9(4) . . . . ? C8 C7 C12 C11 0.6(4) . . . . ? N8 C7 C12 C11 -174.1(3) . . . . ? C10 C11 C12 C7 -0.4(4) . . . . ? C18 C13 C14 C15 -1.3(4) . . . . ? N8 C13 C14 C15 172.6(3) . . . . ? C13 C14 C15 C16 1.0(4) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C14 C13 C18 C17 0.6(4) . . . . ? N8 C13 C18 C17 -173.5(3) . . . . ? C16 C17 C18 C13 0.5(4) . . . . ? N2 C2 N1 C1 175.8(2) . . . . ? N7 C2 N1 C1 -4.0(4) . . . . ? N6 C1 N1 C2 2.0(4) . . . . ? N8 C1 N1 C2 -179.0(2) . . . . ? N1 C2 N2 C3 -177.0(2) . . . . ? N7 C2 N2 C3 2.7(4) . . . . ? N9 C3 N2 C2 173.3(2) . . . . ? N3 C3 N2 C2 -7.1(4) . . . . ? N4 C4 N3 C3 -179.1(2) . . . . ? N7 C4 N3 C3 2.5(4) . . . . ? N2 C3 N3 C4 4.4(4) . . . . ? N9 C3 N3 C4 -176.0(2) . . . . ? N3 C4 N4 C5 -176.1(2) . . . . ? N7 C4 N4 C5 2.3(4) . . . . ? N10 C5 N4 C4 -178.6(2) . . . . ? N5 C5 N4 C4 1.4(4) . . . . ? N6 C6 N5 C5 -177.8(2) . . . . ? N7 C6 N5 C5 2.5(4) . . . . ? N10 C5 N5 C6 176.1(2) . . . . ? N4 C5 N5 C6 -3.9(4) . . . . ? N5 C6 N6 C1 175.9(3) . . . . ? N7 C6 N6 C1 -4.4(4) . . . . ? N1 C1 N6 C6 2.3(4) . . . . ? N8 C1 N6 C6 -176.7(2) . . . . ? N3 C4 N7 C6 175.0(2) . . . . ? N4 C4 N7 C6 -3.5(4) . . . . ? N3 C4 N7 C2 -6.3(4) . . . . ? N4 C4 N7 C2 175.3(2) . . . . ? N6 C6 N7 C4 -178.8(2) . . . . ? N5 C6 N7 C4 0.9(4) . . . . ? N6 C6 N7 C2 2.5(4) . . . . ? N5 C6 N7 C2 -177.8(2) . . . . ? N2 C2 N7 C4 3.5(4) . . . . ? N1 C2 N7 C4 -176.8(2) . . . . ? N2 C2 N7 C6 -177.7(2) . . . . ? N1 C2 N7 C6 2.0(4) . . . . ? N6 C1 N8 C7 -175.4(2) . . . . ? N1 C1 N8 C7 5.5(4) . . . . ? N6 C1 N8 C13 1.9(4) . . . . ? N1 C1 N8 C13 -177.2(2) . . . . ? C12 C7 N8 C1 -117.9(3) . . . . ? C8 C7 N8 C1 67.5(4) . . . . ? C12 C7 N8 C13 64.6(3) . . . . ? C8 C7 N8 C13 -110.0(3) . . . . ? C18 C13 N8 C1 -108.2(3) . . . . ? C14 C13 N8 C1 77.7(4) . . . . ? C18 C13 N8 C7 69.3(3) . . . . ? C14 C13 N8 C7 -104.7(3) . . . . ? N2 C3 N9 C19 176.4(2) . . . . ? N3 C3 N9 C19 -3.2(4) . . . . ? N2 C3 N9 C21 -4.7(4) . . . . ? N3 C3 N9 C21 175.7(2) . . . . ? C20 C19 N9 C3 94.0(3) . . . . ? C20 C19 N9 C21 -85.0(3) . . . . ? C22 C21 N9 C3 92.1(3) . . . . ? C22 C21 N9 C19 -88.9(3) . . . . ? N5 C5 N10 C23 179.2(2) . . . . ? N4 C5 N10 C23 -0.8(4) . . . . ? N5 C5 N10 C25 3.9(4) . . . . ? N4 C5 N10 C25 -176.0(2) . . . . ? C24 C23 N10 C5 -83.4(3) . . . . ? C24 C23 N10 C25 92.1(3) . . . . ? C26 C25 N10 C5 -102.4(3) . . . . ? C26 C25 N10 C23 82.2(3) . . . . ? C29 C27 C28 C29 1.2(5) . . . 2_567 ? C30 C27 C28 C29 -177.3(3) . . . 2_567 ? C28 C27 C29 C28 -1.2(5) . . . 2_567 ? C30 C27 C29 C28 177.3(3) . . . 2_567 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.257 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.061 # Attachment 'ansc125_0m.cif' data_ansc125_0m _database_code_depnum_ccdc_archive 'CCDC 804315' #TrackingRef 'ansc125_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Hexaphenylmelem ; _chemical_name_common Hexaphenylmelem _chemical_formula_moiety 'C42 H30 N10, 3(C H3 N O2)' _chemical_formula_sum 'C45 H39 N13 O6' _chemical_formula_weight 857.89 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' _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 8.3533(12) _cell_length_b 15.991(2) _cell_length_c 17.814(3) _cell_angle_alpha 111.035(7) _cell_angle_beta 95.130(8) _cell_angle_gamma 95.873(6) _cell_volume 2188.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1445 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 20.89 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.091 _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 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19832 _diffrn_reflns_av_R_equivalents 0.1309 _diffrn_reflns_av_sigmaI/netI 0.2451 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.11 _reflns_number_total 7568 _reflns_number_gt 2425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. PROBLEM: Ratio Observed / Unique Reflections too Low .... 32 Perc. RESPONSE: The diffraction power of the crystal was very poor, i.e., it has shown no reflections beyond 50 deg. 2Theta. Cut-off at lower angle would increase the obsd/unique ratio, but on the expense of bond precision. ; _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^)+(0.0946P)^2^+0.4764P] 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 7568 _refine_ls_number_parameters 580 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2634 _refine_ls_R_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.2678 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.004 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 N1 N 0.1000(6) 0.8293(3) 0.2368(3) 0.0373(13) Uani 1 1 d . . . N2 N -0.0254(6) 0.9421(3) 0.3198(3) 0.0405(14) Uani 1 1 d . . . N3 N 0.0558(6) 1.0983(3) 0.3370(3) 0.0375(13) Uani 1 1 d . . . N4 N 0.2673(6) 1.1350(3) 0.2754(3) 0.0359(13) Uani 1 1 d . . . N5 N 0.4070(6) 1.0172(3) 0.1920(3) 0.0342(13) Uani 1 1 d . . . N6 N 0.3213(6) 0.8688(3) 0.1706(3) 0.0358(13) Uani 1 1 d . . . N7 N 0.1897(6) 0.9816(3) 0.2564(3) 0.0323(13) Uani 1 1 d . . . N8 N 0.2213(6) 0.7214(3) 0.1459(3) 0.0404(14) Uani 1 1 d . . . N9 N -0.1577(6) 1.0552(3) 0.3954(3) 0.0393(14) Uani 1 1 d . . . N10 N 0.4762(6) 1.1653(3) 0.2095(3) 0.0386(14) Uani 1 1 d . . . C1 C 0.2119(8) 0.8113(4) 0.1864(4) 0.0392(17) Uani 1 1 d . . . C2 C 0.0850(7) 0.9162(4) 0.2717(4) 0.0367(16) Uani 1 1 d . . . C3 C -0.0385(8) 1.0310(4) 0.3491(4) 0.0363(16) Uani 1 1 d . . . C4 C 0.1682(8) 1.0733(4) 0.2903(4) 0.0346(16) Uani 1 1 d . . . C5 C 0.3780(8) 1.1045(4) 0.2266(4) 0.0371(16) Uani 1 1 d . . . C6 C 0.3060(8) 0.9562(4) 0.2065(4) 0.0381(17) Uani 1 1 d . . . C7 C 0.3159(8) 0.6936(4) 0.0813(5) 0.050(2) Uani 1 1 d . . . C8 C 0.2837(10) 0.7098(4) 0.0115(5) 0.062(2) Uani 1 1 d . . . H8 H 0.1958 0.7414 0.0059 0.074 Uiso 1 1 calc R . . C9 C 0.3762(14) 0.6813(6) -0.0506(5) 0.094(3) Uani 1 1 d . . . H9 H 0.3551 0.6945 -0.0981 0.113 Uiso 1 1 calc R . . C10 C 0.5005(16) 0.6330(6) -0.0426(8) 0.119(5) Uani 1 1 d . . . H10 H 0.5627 0.6106 -0.0858 0.143 Uiso 1 1 calc R . . C11 C 0.5336(12) 0.6178(6) 0.0268(8) 0.105(4) Uani 1 1 d . . . H11 H 0.6220 0.5866 0.0322 0.126 Uiso 1 1 calc R . . C12 C 0.4440(9) 0.6459(5) 0.0888(5) 0.067(2) Uani 1 1 d . . . H12 H 0.4680 0.6335 0.1366 0.081 Uiso 1 1 calc R . . C13 C 0.1209(8) 0.6496(4) 0.1607(4) 0.0395(17) Uani 1 1 d . . . C14 C -0.0026(9) 0.5985(5) 0.1023(5) 0.058(2) Uani 1 1 d . . . H14 H -0.0256 0.6108 0.0544 0.070 Uiso 1 1 calc R . . C15 C -0.0970(10) 0.5263(5) 0.1143(5) 0.075(2) Uani 1 1 d . . . H15 H -0.1815 0.4879 0.0735 0.090 Uiso 1 1 calc R . . C16 C -0.0640(10) 0.5130(5) 0.1854(5) 0.062(2) Uani 1 1 d . . . H16 H -0.1298 0.4665 0.1948 0.075 Uiso 1 1 calc R . . C17 C 0.0600(10) 0.5644(5) 0.2426(5) 0.058(2) Uani 1 1 d . . . H17 H 0.0823 0.5528 0.2909 0.069 Uiso 1 1 calc R . . C18 C 0.1573(8) 0.6358(4) 0.2312(4) 0.0463(18) Uani 1 1 d . . . H18 H 0.2446 0.6726 0.2711 0.056 Uiso 1 1 calc R . . C19 C -0.2684(8) 0.9865(4) 0.4074(4) 0.0349(16) Uani 1 1 d . . . C20 C -0.3913(8) 0.9366(4) 0.3488(4) 0.0440(18) Uani 1 1 d . . . H20 H -0.4030 0.9453 0.2987 0.053 Uiso 1 1 calc R . . C21 C -0.5025(8) 0.8718(5) 0.3612(5) 0.0502(19) Uani 1 1 d . . . H21 H -0.5896 0.8366 0.3205 0.060 Uiso 1 1 calc R . . C22 C -0.4796(9) 0.8618(5) 0.4345(5) 0.0510(19) Uani 1 1 d . . . H22 H -0.5528 0.8182 0.4438 0.061 Uiso 1 1 calc R . . C23 C -0.3566(9) 0.9116(5) 0.4948(5) 0.055(2) Uani 1 1 d . . . H23 H -0.3450 0.9036 0.5452 0.066 Uiso 1 1 calc R . . C24 C -0.2472(8) 0.9753(4) 0.4799(4) 0.0460(18) Uani 1 1 d . . . H24 H -0.1591 1.0103 0.5202 0.055 Uiso 1 1 calc R . . C25 C -0.1916(8) 1.1470(4) 0.4287(4) 0.0427(17) Uani 1 1 d . . . C26 C -0.3380(8) 1.1665(5) 0.4029(4) 0.0510(19) Uani 1 1 d . . . H26 H -0.4117 1.1206 0.3614 0.061 Uiso 1 1 calc R . . C27 C -0.3794(10) 1.2536(5) 0.4373(5) 0.061(2) Uani 1 1 d . . . H27 H -0.4797 1.2674 0.4186 0.074 Uiso 1 1 calc R . . C28 C -0.2733(11) 1.3184(6) 0.4983(5) 0.072(2) Uani 1 1 d . . . H28 H -0.3012 1.3773 0.5233 0.086 Uiso 1 1 calc R . . C29 C -0.1270(10) 1.2986(5) 0.5234(5) 0.074(3) Uani 1 1 d . . . H29 H -0.0517 1.3448 0.5638 0.089 Uiso 1 1 calc R . . C30 C -0.0874(9) 1.2113(5) 0.4903(5) 0.063(2) Uani 1 1 d . . . H30 H 0.0110 1.1969 0.5104 0.076 Uiso 1 1 calc R . . C31 C 0.4483(8) 1.2597(4) 0.2308(4) 0.0419(17) Uani 1 1 d . . . C32 C 0.3033(8) 1.2758(4) 0.1975(4) 0.054(2) Uani 1 1 d . . . H32 H 0.2233 1.2272 0.1631 0.064 Uiso 1 1 calc R . . C33 C 0.2790(10) 1.3658(5) 0.2161(5) 0.065(2) Uani 1 1 d . . . H33 H 0.1800 1.3791 0.1955 0.078 Uiso 1 1 calc R . . C34 C 0.3974(11) 1.4350(5) 0.2641(5) 0.074(3) Uani 1 1 d . . . H34 H 0.3783 1.4959 0.2773 0.089 Uiso 1 1 calc R . . C35 C 0.5417(10) 1.4179(5) 0.2931(5) 0.069(2) Uani 1 1 d . . . H35 H 0.6244 1.4666 0.3243 0.083 Uiso 1 1 calc R . . C36 C 0.5677(9) 1.3277(4) 0.2767(4) 0.052(2) Uani 1 1 d . . . H36 H 0.6671 1.3147 0.2973 0.063 Uiso 1 1 calc R . . C37 C 0.6050(8) 1.1380(4) 0.1597(4) 0.0387(17) Uani 1 1 d . . . C38 C 0.5731(8) 1.1130(4) 0.0787(4) 0.0443(18) Uani 1 1 d . . . H38 H 0.4662 1.1108 0.0542 0.053 Uiso 1 1 calc R . . C39 C 0.6968(10) 1.0901(5) 0.0307(5) 0.057(2) Uani 1 1 d . . . H39 H 0.6751 1.0719 -0.0266 0.068 Uiso 1 1 calc R . . C40 C 0.8499(10) 1.0944(5) 0.0675(5) 0.059(2) Uani 1 1 d . . . H40 H 0.9350 1.0791 0.0353 0.070 Uiso 1 1 calc R . . C41 C 0.8822(8) 1.1200(5) 0.1493(5) 0.057(2) Uani 1 1 d . . . H41 H 0.9894 1.1231 0.1740 0.068 Uiso 1 1 calc R . . C42 C 0.7581(9) 1.1417(4) 0.1967(5) 0.054(2) Uani 1 1 d . . . H42 H 0.7790 1.1588 0.2539 0.065 Uiso 1 1 calc R . . O1 O 0.5621(8) 0.6467(4) 0.2860(4) 0.104(2) Uani 1 1 d . . . O2 O 0.7340(8) 0.6665(4) 0.3886(4) 0.104(2) Uani 1 1 d . . . N11 N 0.6927(9) 0.6776(4) 0.3265(6) 0.073(2) Uani 1 1 d . . . C43 C 0.8081(9) 0.7358(5) 0.3000(5) 0.082(3) Uani 1 1 d . . . H43A H 0.8035 0.7997 0.3314 0.123 Uiso 1 1 calc R . . H43B H 0.7779 0.7232 0.2422 0.123 Uiso 1 1 calc R . . H43C H 0.9187 0.7227 0.3090 0.123 Uiso 1 1 calc R . . O3 O 0.0991(15) 0.4748(6) 0.4121(8) 0.220(6) Uani 1 1 d . . . O4 O -0.0342(12) 0.3638(9) 0.3292(7) 0.219(6) Uani 1 1 d . . . N12 N 0.0728(12) 0.4024(7) 0.3837(7) 0.104(3) Uani 1 1 d . . . C44 C 0.1756(13) 0.3423(7) 0.4037(7) 0.130(4) Uani 1 1 d . . . H44A H 0.1082 0.2861 0.3983 0.195 Uiso 1 1 calc R . . H44B H 0.2301 0.3723 0.4596 0.195 Uiso 1 1 calc R . . H44C H 0.2572 0.3284 0.3664 0.195 Uiso 1 1 calc R . . O5 O 0.9622(7) 0.9035(5) 0.1060(4) 0.093(2) Uani 1 1 d . . . O6 O 0.7960(9) 0.8388(6) -0.0007(5) 0.152(4) Uani 1 1 d . . . N13 N 0.8278(9) 0.8695(5) 0.0732(5) 0.073(2) Uani 1 1 d . . . C45 C 0.6907(9) 0.8771(6) 0.1175(5) 0.074(2) Uani 1 1 d . . . H45A H 0.7218 0.8712 0.1695 0.111 Uiso 1 1 calc R . . H45B H 0.6016 0.8290 0.0857 0.111 Uiso 1 1 calc R . . H45C H 0.6553 0.9362 0.1273 0.111 Uiso 1 1 calc R . . 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 N1 0.041(3) 0.016(3) 0.060(4) 0.016(3) 0.021(3) 0.010(3) N2 0.044(4) 0.019(3) 0.066(4) 0.021(3) 0.017(3) 0.009(3) N3 0.033(3) 0.023(3) 0.061(4) 0.021(3) 0.013(3) 0.005(3) N4 0.033(3) 0.020(3) 0.059(4) 0.018(3) 0.011(3) 0.006(3) N5 0.033(3) 0.021(3) 0.053(3) 0.020(3) 0.009(3) 0.000(2) N6 0.031(3) 0.019(3) 0.061(4) 0.018(3) 0.009(3) 0.002(2) N7 0.031(3) 0.018(3) 0.054(3) 0.018(3) 0.014(3) 0.006(2) N8 0.044(3) 0.021(3) 0.063(4) 0.020(3) 0.021(3) 0.003(3) N9 0.038(3) 0.025(3) 0.060(4) 0.018(3) 0.018(3) 0.010(3) N10 0.036(3) 0.016(3) 0.071(4) 0.021(3) 0.016(3) 0.008(3) C1 0.036(4) 0.019(4) 0.061(5) 0.015(3) -0.004(4) 0.007(3) C2 0.025(4) 0.032(4) 0.057(5) 0.023(4) 0.005(4) 0.001(3) C3 0.034(4) 0.032(4) 0.048(4) 0.020(3) 0.003(3) 0.006(3) C4 0.034(4) 0.018(4) 0.054(4) 0.015(3) 0.003(4) 0.008(3) C5 0.032(4) 0.027(4) 0.058(4) 0.021(3) 0.011(4) 0.007(3) C6 0.037(4) 0.027(4) 0.057(4) 0.020(3) 0.016(4) 0.013(3) C7 0.054(5) 0.017(4) 0.084(6) 0.019(4) 0.031(4) 0.003(3) C8 0.092(6) 0.026(4) 0.075(6) 0.024(4) 0.028(5) 0.000(4) C9 0.162(10) 0.030(5) 0.084(7) 0.017(5) 0.053(7) -0.024(6) C10 0.149(11) 0.025(6) 0.169(12) 0.002(7) 0.117(10) -0.009(6) C11 0.093(8) 0.063(7) 0.179(12) 0.047(8) 0.086(9) 0.037(6) C12 0.065(6) 0.045(5) 0.104(7) 0.034(5) 0.038(5) 0.021(4) C13 0.033(4) 0.023(4) 0.068(5) 0.021(4) 0.015(4) 0.007(3) C14 0.051(5) 0.038(5) 0.086(6) 0.028(4) 0.004(5) -0.004(4) C15 0.079(6) 0.048(5) 0.094(7) 0.029(5) 0.016(5) -0.017(5) C16 0.061(6) 0.034(5) 0.101(7) 0.035(5) 0.022(5) -0.002(4) C17 0.067(6) 0.034(5) 0.097(6) 0.047(5) 0.031(5) 0.018(4) C18 0.047(5) 0.036(4) 0.060(5) 0.020(4) 0.011(4) 0.008(4) C19 0.033(4) 0.029(4) 0.047(4) 0.017(3) 0.010(3) 0.007(3) C20 0.045(5) 0.034(4) 0.062(5) 0.025(4) 0.012(4) 0.010(4) C21 0.040(4) 0.043(5) 0.073(5) 0.028(4) 0.007(4) 0.005(4) C22 0.042(5) 0.038(4) 0.081(6) 0.030(4) 0.011(4) 0.009(4) C23 0.056(5) 0.050(5) 0.069(5) 0.036(4) 0.008(5) 0.005(4) C24 0.041(4) 0.046(5) 0.056(5) 0.022(4) 0.013(4) 0.011(4) C25 0.043(4) 0.028(4) 0.063(5) 0.021(4) 0.017(4) 0.009(4) C26 0.055(5) 0.037(4) 0.075(5) 0.033(4) 0.014(4) 0.016(4) C27 0.065(6) 0.054(5) 0.087(6) 0.045(5) 0.026(5) 0.024(5) C28 0.077(7) 0.049(6) 0.106(7) 0.034(5) 0.043(6) 0.032(5) C29 0.069(6) 0.040(5) 0.102(7) 0.009(5) 0.022(5) 0.007(5) C30 0.054(5) 0.045(5) 0.083(6) 0.013(4) 0.007(5) 0.017(4) C31 0.044(4) 0.022(4) 0.070(5) 0.027(4) 0.016(4) 0.008(3) C32 0.052(5) 0.031(4) 0.097(6) 0.040(4) 0.029(4) 0.013(4) C33 0.055(5) 0.055(6) 0.113(7) 0.056(5) 0.032(5) 0.024(5) C34 0.079(7) 0.033(5) 0.128(8) 0.041(5) 0.044(6) 0.018(5) C35 0.070(6) 0.026(5) 0.114(7) 0.028(4) 0.024(5) -0.001(4) C36 0.051(5) 0.027(4) 0.082(5) 0.025(4) 0.013(4) 0.003(4) C37 0.041(5) 0.018(4) 0.062(5) 0.021(3) 0.007(4) -0.001(3) C38 0.046(5) 0.029(4) 0.062(5) 0.020(4) 0.010(4) 0.010(3) C39 0.070(6) 0.042(5) 0.069(5) 0.028(4) 0.017(5) 0.017(4) C40 0.059(6) 0.047(5) 0.091(7) 0.044(5) 0.031(5) 0.015(4) C41 0.031(4) 0.051(5) 0.101(7) 0.044(5) 0.009(5) 0.004(4) C42 0.042(5) 0.048(5) 0.077(5) 0.031(4) 0.008(4) 0.001(4) O1 0.073(5) 0.068(4) 0.168(6) 0.055(4) -0.006(5) -0.021(4) O2 0.104(5) 0.095(5) 0.131(6) 0.074(5) -0.003(5) -0.011(4) N11 0.054(5) 0.045(5) 0.123(7) 0.033(5) 0.020(5) 0.005(4) C43 0.066(6) 0.048(5) 0.152(8) 0.058(6) 0.039(6) 0.004(4) O3 0.288(14) 0.042(5) 0.315(13) 0.035(7) 0.081(11) 0.037(7) O4 0.101(8) 0.282(15) 0.245(13) 0.077(11) 0.002(8) -0.007(9) N12 0.083(7) 0.085(8) 0.141(9) 0.036(7) 0.035(6) -0.004(6) C44 0.154(10) 0.125(10) 0.177(11) 0.108(9) 0.067(9) 0.081(9) O5 0.046(4) 0.131(6) 0.112(5) 0.067(4) -0.004(4) -0.008(4) O6 0.087(5) 0.230(10) 0.094(5) 0.016(6) 0.035(5) -0.033(5) N13 0.057(5) 0.089(6) 0.067(5) 0.027(4) 0.011(5) -0.006(4) C45 0.062(6) 0.085(7) 0.088(6) 0.039(5) 0.037(5) 0.016(5) _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 N1 C2 1.327(7) . ? N1 C1 1.335(8) . ? N2 C2 1.311(7) . ? N2 C3 1.347(7) . ? N3 C4 1.308(7) . ? N3 C3 1.360(7) . ? N4 C5 1.335(7) . ? N4 C4 1.338(7) . ? N5 C6 1.336(7) . ? N5 C5 1.365(7) . ? N6 C6 1.337(7) . ? N6 C1 1.349(8) . ? N7 C6 1.369(7) . ? N7 C4 1.409(7) . ? N7 C2 1.413(7) . ? N8 C1 1.372(7) . ? N8 C7 1.419(8) . ? N8 C13 1.467(8) . ? N9 C3 1.348(7) . ? N9 C25 1.440(7) . ? N9 C19 1.451(8) . ? N10 C5 1.344(7) . ? N10 C37 1.457(8) . ? N10 C31 1.467(7) . ? C7 C8 1.369(9) . ? C7 C12 1.399(9) . ? C8 C9 1.376(10) . ? C8 H8 0.9500 . ? C9 C10 1.382(14) . ? C9 H9 0.9500 . ? C10 C11 1.354(14) . ? C10 H10 0.9500 . ? C11 C12 1.358(11) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.356(9) . ? C13 C18 1.365(8) . ? C14 C15 1.422(10) . ? C14 H14 0.9500 . ? C15 C16 1.368(9) . ? C15 H15 0.9500 . ? C16 C17 1.351(9) . ? C16 H16 0.9500 . ? C17 C18 1.418(9) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.350(8) . ? C19 C24 1.364(8) . ? C20 C21 1.410(9) . ? C20 H20 0.9500 . ? C21 C22 1.371(9) . ? C21 H21 0.9500 . ? C22 C23 1.365(9) . ? C22 H22 0.9500 . ? C23 C24 1.411(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.363(9) . ? C25 C26 1.373(8) . ? C26 C27 1.399(9) . ? C26 H26 0.9500 . ? C27 C28 1.369(10) . ? C27 H27 0.9500 . ? C28 C29 1.371(10) . ? C28 H28 0.9500 . ? C29 C30 1.394(9) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C36 1.356(8) . ? C31 C32 1.390(8) . ? C32 C33 1.397(9) . ? C32 H32 0.9500 . ? C33 C34 1.371(10) . ? C33 H33 0.9500 . ? C34 C35 1.361(10) . ? C34 H34 0.9500 . ? C35 C36 1.410(9) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C38 1.345(8) . ? C37 C42 1.371(8) . ? C38 C39 1.395(9) . ? C38 H38 0.9500 . ? C39 C40 1.367(9) . ? C39 H39 0.9500 . ? C40 C41 1.357(9) . ? C40 H40 0.9500 . ? C41 C42 1.388(9) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? O1 N11 1.204(8) . ? O2 N11 1.208(8) . ? N11 C43 1.494(9) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? O3 N12 1.073(10) . ? O4 N12 1.193(11) . ? N12 C44 1.465(12) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? O5 N13 1.194(8) . ? O6 N13 1.221(8) . ? N13 C45 1.439(9) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 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 C2 N1 C1 115.5(5) . . ? C2 N2 C3 117.4(6) . . ? C4 N3 C3 116.2(5) . . ? C5 N4 C4 117.0(5) . . ? C6 N5 C5 114.8(5) . . ? C6 N6 C1 114.3(5) . . ? C6 N7 C4 120.3(5) . . ? C6 N7 C2 120.6(5) . . ? C4 N7 C2 119.0(5) . . ? C1 N8 C7 121.0(6) . . ? C1 N8 C13 121.9(6) . . ? C7 N8 C13 116.8(5) . . ? C3 N9 C25 123.0(6) . . ? C3 N9 C19 120.0(5) . . ? C25 N9 C19 116.8(5) . . ? C5 N10 C37 121.2(5) . . ? C5 N10 C31 122.4(5) . . ? C37 N10 C31 116.0(5) . . ? N1 C1 N6 129.5(6) . . ? N1 C1 N8 116.0(6) . . ? N6 C1 N8 114.5(6) . . ? N2 C2 N1 121.3(6) . . ? N2 C2 N7 119.6(6) . . ? N1 C2 N7 119.1(6) . . ? N2 C3 N9 116.2(6) . . ? N2 C3 N3 126.8(6) . . ? N9 C3 N3 117.0(6) . . ? N3 C4 N4 120.4(6) . . ? N3 C4 N7 120.8(6) . . ? N4 C4 N7 118.8(6) . . ? N4 C5 N10 117.8(6) . . ? N4 C5 N5 127.6(6) . . ? N10 C5 N5 114.6(6) . . ? N5 C6 N6 117.9(6) . . ? N5 C6 N7 121.4(5) . . ? N6 C6 N7 120.7(6) . . ? C8 C7 C12 119.1(7) . . ? C8 C7 N8 122.3(6) . . ? C12 C7 N8 118.5(7) . . ? C9 C8 C7 121.1(8) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 118.9(9) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 119.9(10) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 121.9(10) . . ? C10 C11 H11 119.0 . . ? C12 C11 H11 119.1 . . ? C11 C12 C7 119.0(8) . . ? C11 C12 H12 120.5 . . ? C7 C12 H12 120.5 . . ? C14 C13 C18 123.0(7) . . ? C14 C13 N8 118.0(6) . . ? C18 C13 N8 119.0(6) . . ? C13 C14 C15 118.6(8) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C16 C15 C14 118.9(8) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 121.4(8) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 120.5(7) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 117.5(7) . . ? C13 C18 H18 121.2 . . ? C17 C18 H18 121.2 . . ? C20 C19 C24 121.2(7) . . ? C20 C19 N9 120.5(6) . . ? C24 C19 N9 118.3(6) . . ? C19 C20 C21 120.8(7) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 117.2(7) . . ? C22 C21 H21 121.4 . . ? C20 C21 H21 121.4 . . ? C23 C22 C21 123.1(7) . . ? C23 C22 H22 118.4 . . ? C21 C22 H22 118.4 . . ? C22 C23 C24 118.0(7) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C19 C24 C23 119.7(7) . . ? C19 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C30 C25 C26 120.3(6) . . ? C30 C25 N9 120.6(6) . . ? C26 C25 N9 118.8(6) . . ? C25 C26 C27 120.6(7) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 119.0(7) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 120.5 . . ? C27 C28 C29 120.2(7) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C28 C29 C30 120.8(8) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C25 C30 C29 119.1(7) . . ? C25 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C36 C31 C32 122.3(6) . . ? C36 C31 N10 119.6(6) . . ? C32 C31 N10 117.9(6) . . ? C31 C32 C33 117.7(7) . . ? C31 C32 H32 121.1 . . ? C33 C32 H32 121.1 . . ? C34 C33 C32 120.3(7) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C35 C34 C33 121.1(7) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C34 C35 C36 119.7(8) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C31 C36 C35 118.8(7) . . ? C31 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? C38 C37 C42 121.1(7) . . ? C38 C37 N10 119.5(6) . . ? C42 C37 N10 119.3(6) . . ? C37 C38 C39 120.0(7) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C40 C39 C38 118.9(7) . . ? C40 C39 H39 120.6 . . ? C38 C39 H39 120.6 . . ? C41 C40 C39 121.1(7) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C40 C41 C42 119.7(7) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C37 C42 C41 119.1(7) . . ? C37 C42 H42 120.4 . . ? C41 C42 H42 120.5 . . ? O2 N11 O1 123.8(8) . . ? O2 N11 C43 118.2(8) . . ? O1 N11 C43 118.0(8) . . ? N11 C43 H43A 109.5 . . ? N11 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N11 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O3 N12 O4 123.5(14) . . ? O3 N12 C44 122.4(13) . . ? O4 N12 C44 113.8(12) . . ? N12 C44 H44A 109.5 . . ? N12 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? N12 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? O5 N13 O6 121.3(8) . . ? O5 N13 C45 121.9(8) . . ? O6 N13 C45 115.9(8) . . ? N13 C45 H45A 109.5 . . ? N13 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? N13 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? 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 C2 N1 C1 N6 6.0(9) . . . . ? C2 N1 C1 N8 -176.0(5) . . . . ? C6 N6 C1 N1 -5.5(9) . . . . ? C6 N6 C1 N8 176.5(5) . . . . ? C7 N8 C1 N1 169.5(6) . . . . ? C13 N8 C1 N1 -3.4(8) . . . . ? C7 N8 C1 N6 -12.1(8) . . . . ? C13 N8 C1 N6 175.0(6) . . . . ? C3 N2 C2 N1 -176.3(6) . . . . ? C3 N2 C2 N7 3.3(8) . . . . ? C1 N1 C2 N2 177.1(5) . . . . ? C1 N1 C2 N7 -2.6(8) . . . . ? C6 N7 C2 N2 179.9(5) . . . . ? C4 N7 C2 N2 -2.8(8) . . . . ? C6 N7 C2 N1 -0.4(8) . . . . ? C4 N7 C2 N1 176.9(5) . . . . ? C2 N2 C3 N9 177.1(5) . . . . ? C2 N2 C3 N3 -3.0(9) . . . . ? C25 N9 C3 N2 -177.6(6) . . . . ? C19 N9 C3 N2 -3.3(8) . . . . ? C25 N9 C3 N3 2.5(9) . . . . ? C19 N9 C3 N3 176.8(5) . . . . ? C4 N3 C3 N2 1.8(9) . . . . ? C4 N3 C3 N9 -178.3(5) . . . . ? C3 N3 C4 N4 -179.6(5) . . . . ? C3 N3 C4 N7 -1.0(8) . . . . ? C5 N4 C4 N3 -179.4(5) . . . . ? C5 N4 C4 N7 2.0(8) . . . . ? C6 N7 C4 N3 178.9(5) . . . . ? C2 N7 C4 N3 1.6(8) . . . . ? C6 N7 C4 N4 -2.5(8) . . . . ? C2 N7 C4 N4 -179.8(5) . . . . ? C4 N4 C5 N10 178.6(5) . . . . ? C4 N4 C5 N5 -2.7(9) . . . . ? C37 N10 C5 N4 177.2(5) . . . . ? C31 N10 C5 N4 -10.5(9) . . . . ? C37 N10 C5 N5 -1.7(8) . . . . ? C31 N10 C5 N5 170.6(5) . . . . ? C6 N5 C5 N4 3.5(9) . . . . ? C6 N5 C5 N10 -177.8(5) . . . . ? C5 N5 C6 N6 176.1(5) . . . . ? C5 N5 C6 N7 -3.6(8) . . . . ? C1 N6 C6 N5 -178.2(5) . . . . ? C1 N6 C6 N7 1.6(8) . . . . ? C4 N7 C6 N5 3.4(8) . . . . ? C2 N7 C6 N5 -179.3(5) . . . . ? C4 N7 C6 N6 -176.4(5) . . . . ? C2 N7 C6 N6 0.9(8) . . . . ? C1 N8 C7 C8 -61.9(9) . . . . ? C13 N8 C7 C8 111.3(7) . . . . ? C1 N8 C7 C12 119.6(7) . . . . ? C13 N8 C7 C12 -67.1(8) . . . . ? C12 C7 C8 C9 -0.9(11) . . . . ? N8 C7 C8 C9 -179.3(7) . . . . ? C7 C8 C9 C10 1.9(12) . . . . ? C8 C9 C10 C11 -2.7(14) . . . . ? C9 C10 C11 C12 2.4(16) . . . . ? C10 C11 C12 C7 -1.3(14) . . . . ? C8 C7 C12 C11 0.5(11) . . . . ? N8 C7 C12 C11 179.0(7) . . . . ? C1 N8 C13 C14 107.9(7) . . . . ? C7 N8 C13 C14 -65.3(8) . . . . ? C1 N8 C13 C18 -73.4(7) . . . . ? C7 N8 C13 C18 113.4(7) . . . . ? C18 C13 C14 C15 -1.1(10) . . . . ? N8 C13 C14 C15 177.5(6) . . . . ? C13 C14 C15 C16 2.5(11) . . . . ? C14 C15 C16 C17 -2.8(12) . . . . ? C15 C16 C17 C18 1.7(11) . . . . ? C14 C13 C18 C17 0.0(9) . . . . ? N8 C13 C18 C17 -178.6(5) . . . . ? C16 C17 C18 C13 -0.3(10) . . . . ? C3 N9 C19 C20 -77.9(7) . . . . ? C25 N9 C19 C20 96.8(7) . . . . ? C3 N9 C19 C24 103.7(7) . . . . ? C25 N9 C19 C24 -81.7(7) . . . . ? C24 C19 C20 C21 0.5(9) . . . . ? N9 C19 C20 C21 -177.9(5) . . . . ? C19 C20 C21 C22 -0.3(9) . . . . ? C20 C21 C22 C23 0.5(10) . . . . ? C21 C22 C23 C24 -0.9(10) . . . . ? C20 C19 C24 C23 -0.9(9) . . . . ? N9 C19 C24 C23 177.5(6) . . . . ? C22 C23 C24 C19 1.1(9) . . . . ? C3 N9 C25 C30 -71.3(9) . . . . ? C19 N9 C25 C30 114.2(7) . . . . ? C3 N9 C25 C26 115.1(7) . . . . ? C19 N9 C25 C26 -59.4(8) . . . . ? C30 C25 C26 C27 2.5(11) . . . . ? N9 C25 C26 C27 176.2(6) . . . . ? C25 C26 C27 C28 -1.4(11) . . . . ? C26 C27 C28 C29 1.8(12) . . . . ? C27 C28 C29 C30 -3.3(13) . . . . ? C26 C25 C30 C29 -3.8(11) . . . . ? N9 C25 C30 C29 -177.4(7) . . . . ? C28 C29 C30 C25 4.3(12) . . . . ? C5 N10 C31 C36 124.4(7) . . . . ? C37 N10 C31 C36 -63.0(8) . . . . ? C5 N10 C31 C32 -60.5(9) . . . . ? C37 N10 C31 C32 112.1(7) . . . . ? C36 C31 C32 C33 -3.4(10) . . . . ? N10 C31 C32 C33 -178.3(6) . . . . ? C31 C32 C33 C34 1.7(11) . . . . ? C32 C33 C34 C35 1.3(12) . . . . ? C33 C34 C35 C36 -2.8(13) . . . . ? C32 C31 C36 C35 2.0(11) . . . . ? N10 C31 C36 C35 176.9(6) . . . . ? C34 C35 C36 C31 1.1(11) . . . . ? C5 N10 C37 C38 89.5(7) . . . . ? C31 N10 C37 C38 -83.2(7) . . . . ? C5 N10 C37 C42 -92.9(7) . . . . ? C31 N10 C37 C42 94.4(7) . . . . ? C42 C37 C38 C39 0.0(9) . . . . ? N10 C37 C38 C39 177.5(6) . . . . ? C37 C38 C39 C40 -0.5(10) . . . . ? C38 C39 C40 C41 0.2(10) . . . . ? C39 C40 C41 C42 0.5(11) . . . . ? C38 C37 C42 C41 0.8(10) . . . . ? N10 C37 C42 C41 -176.8(6) . . . . ? C40 C41 C42 C37 -1.0(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C12 H12 O1 0.95 2.63 3.558(11) 164.4 . C18 H18 O1 0.95 2.73 3.403(9) 128.4 . C45 H45C N5 0.98 2.69 3.452(9) 135.3 . C36 H36 O4 0.95 2.49 3.306(13) 144.3 1_665 C43 H43A N2 0.98 2.65 3.329(9) 127.0 1_655 C41 H41 N4 0.95 2.76 3.689(9) 167.4 1_655 C38 H38 O6 0.95 2.63 3.539(11) 161.3 2_675 C32 H32 O6 0.95 2.68 3.300(11) 123.1 2_675 C40 H40 O6 0.95 2.72 3.494(10) 139.5 2_775 C34 H34 O1 0.95 2.67 3.392(10) 133.3 1_565 C28 H28 O3 0.95 2.58 3.226(14) 125.7 2_576 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.553 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.072 # Attachment 'ansc126_0m.cif' data_ansc126_0m _database_code_depnum_ccdc_archive 'CCDC 804316' #TrackingRef 'ansc126_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Phenylamino-5,8-diethylamino-tri-s-triazin ; _chemical_name_common ; 1-Phenylamino-5,8-diethylamino-tri-s-triazin ; _chemical_formula_moiety '2(C26 H30 N10), 5(C H3 N O2)' _chemical_formula_sum 'C57 H75 N25 O10' _chemical_formula_weight 1270.42 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' _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 12.5530(9) _cell_length_b 15.4588(11) _cell_length_c 18.0530(15) _cell_angle_alpha 83.008(4) _cell_angle_beta 80.797(4) _cell_angle_gamma 67.012(4) _cell_volume 3176.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1995 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 21.70 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.096 _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 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36288 _diffrn_reflns_av_R_equivalents 0.1106 _diffrn_reflns_av_sigmaI/netI 0.1689 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11096 _reflns_number_gt 4113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2007)' _computing_cell_refinement 'Bruker SMART (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 2007)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2007)' _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. PROBLEM: Ratio Observed / Unique Reflections too Low .... 37 Perc. RESPONSE: The diffraction power of the crystal was very poor, i.e., it has shown no reflections beyond 50 deg. 2Theta. Cut-off at lower angle would increase the obsd/unique ratio, but on the expense of bond precision. ; _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^)+(0.0733P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11096 _refine_ls_number_parameters 842 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2224 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1780 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_restrained_S_all 0.871 _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 N1 N 0.7780(3) 0.2854(2) 0.21727(19) 0.0193(9) Uani 1 1 d . . . N2 N 0.9478(3) 0.3131(2) 0.18438(19) 0.0200(9) Uani 1 1 d . . . N3 N 1.1283(3) 0.2007(2) 0.2282(2) 0.0220(9) Uani 1 1 d . . . N4 N 1.1253(3) 0.0760(2) 0.3105(2) 0.0204(9) Uani 1 1 d . . . N5 N 0.9454(3) 0.0504(2) 0.34791(19) 0.0202(9) Uani 1 1 d . . . N6 N 0.7794(3) 0.1489(2) 0.2977(2) 0.0202(9) Uani 1 1 d . . . N7 N 0.9507(3) 0.1799(2) 0.26478(19) 0.0179(9) Uani 1 1 d . . . N8 N 0.6127(3) 0.2537(2) 0.25103(19) 0.0197(9) Uani 1 1 d . . . N9 N 1.1205(3) 0.3341(2) 0.15332(19) 0.0195(9) Uani 1 1 d . . . N10 N 1.1152(3) -0.0460(3) 0.3936(2) 0.0263(10) Uani 1 1 d . . . C1 C 0.7285(4) 0.2281(3) 0.2560(2) 0.0193(11) Uani 1 1 d . . . C2 C 0.8917(4) 0.2602(3) 0.2210(2) 0.0164(11) Uani 1 1 d . . . C3 C 1.0642(4) 0.2813(3) 0.1902(2) 0.0170(11) Uani 1 1 d . . . C4 C 1.0709(4) 0.1514(3) 0.2684(2) 0.0202(11) Uani 1 1 d . . . C5 C 1.0611(4) 0.0294(3) 0.3493(2) 0.0210(11) Uani 1 1 d . . . C6 C 0.8920(4) 0.1249(3) 0.3050(2) 0.0170(11) Uani 1 1 d . . . C7 C 0.5422(3) 0.2124(3) 0.3027(2) 0.0187(11) Uani 1 1 d . . . C8 C 0.5427(3) 0.2090(3) 0.3795(2) 0.0211(11) Uani 1 1 d . . . H8 H 0.5922 0.2317 0.3990 0.025 Uiso 1 1 calc R . . C9 C 0.4712(4) 0.1726(3) 0.4281(3) 0.0258(12) Uani 1 1 d . . . H9 H 0.4731 0.1686 0.4808 0.031 Uiso 1 1 calc R . . C10 C 0.3970(4) 0.1420(3) 0.3999(3) 0.0275(12) Uani 1 1 d . . . H10 H 0.3463 0.1188 0.4335 0.033 Uiso 1 1 calc R . . C11 C 0.3959(4) 0.1449(3) 0.3232(3) 0.0263(12) Uani 1 1 d . . . H11 H 0.3455 0.1230 0.3039 0.032 Uiso 1 1 calc R . . C12 C 0.4693(4) 0.1803(3) 0.2745(2) 0.0216(11) Uani 1 1 d . . . H12 H 0.4693 0.1823 0.2217 0.026 Uiso 1 1 calc R . . C13 C 0.5511(3) 0.3290(3) 0.1996(2) 0.0164(10) Uani 1 1 d . . . C14 C 0.5713(4) 0.3200(3) 0.1235(3) 0.0242(11) Uani 1 1 d . . . H14 H 0.6323 0.2658 0.1035 0.029 Uiso 1 1 calc R . . C15 C 0.5041(4) 0.3885(3) 0.0760(2) 0.0238(11) Uani 1 1 d . . . H15 H 0.5183 0.3817 0.0233 0.029 Uiso 1 1 calc R . . C16 C 0.4150(4) 0.4683(3) 0.1054(3) 0.0249(12) Uani 1 1 d . . . H16 H 0.3671 0.5151 0.0727 0.030 Uiso 1 1 calc R . . C17 C 0.3958(4) 0.4796(3) 0.1819(2) 0.0237(11) Uani 1 1 d . . . H17 H 0.3363 0.5346 0.2017 0.028 Uiso 1 1 calc R . . C18 C 0.4649(4) 0.4094(3) 0.2296(2) 0.0204(11) Uani 1 1 d . . . H18 H 0.4532 0.4165 0.2821 0.024 Uiso 1 1 calc R . . C19 C 1.0604(4) 0.4249(3) 0.1138(2) 0.0243(12) Uani 1 1 d . . . H19A H 0.9913 0.4235 0.0949 0.029 Uiso 1 1 calc R . . H19B H 1.1133 0.4357 0.0700 0.029 Uiso 1 1 calc R . . C20 C 1.0219(4) 0.5050(3) 0.1654(3) 0.0352(13) Uani 1 1 d . . . H20A H 0.9672 0.4956 0.2077 0.053 Uiso 1 1 calc R . . H20B H 0.9836 0.5649 0.1373 0.053 Uiso 1 1 calc R . . H20C H 1.0902 0.5063 0.1844 0.053 Uiso 1 1 calc R . . C21 C 1.2472(3) 0.3064(3) 0.1545(2) 0.0261(12) Uani 1 1 d . . . H21A H 1.2687 0.2741 0.2038 0.031 Uiso 1 1 calc R . . H21B H 1.2662 0.3635 0.1480 0.031 Uiso 1 1 calc R . . C22 C 1.3177(4) 0.2416(3) 0.0926(3) 0.0315(13) Uani 1 1 d . . . H22A H 1.3003 0.1844 0.0995 0.047 Uiso 1 1 calc R . . H22B H 1.4010 0.2247 0.0947 0.047 Uiso 1 1 calc R . . H22C H 1.2974 0.2738 0.0437 0.047 Uiso 1 1 calc R . . C23 C 1.2417(4) -0.0790(3) 0.3977(3) 0.0365(13) Uani 1 1 d . . . H23A H 1.2789 -0.0551 0.3517 0.044 Uiso 1 1 calc R . . H23B H 1.2758 -0.1486 0.3993 0.044 Uiso 1 1 calc R . . C24 C 1.2686(4) -0.0468(3) 0.4657(3) 0.0390(14) Uani 1 1 d . . . H24A H 1.2359 0.0222 0.4642 0.058 Uiso 1 1 calc R . . H24B H 1.3532 -0.0698 0.4656 0.058 Uiso 1 1 calc R . . H24C H 1.2340 -0.0718 0.5116 0.058 Uiso 1 1 calc R . . C25 C 1.0553(4) -0.1035(3) 0.4391(2) 0.0275(12) Uani 1 1 d . . . H25A H 0.9738 -0.0625 0.4558 0.033 Uiso 1 1 calc R . . H25B H 1.0947 -0.1319 0.4844 0.033 Uiso 1 1 calc R . . C26 C 1.0553(4) -0.1810(3) 0.3950(3) 0.0379(14) Uani 1 1 d . . . H26A H 1.0124 -0.1529 0.3517 0.057 Uiso 1 1 calc R . . H26B H 1.0178 -0.2193 0.4274 0.057 Uiso 1 1 calc R . . H26C H 1.1358 -0.2208 0.3774 0.057 Uiso 1 1 calc R . . N11 N 0.7875(3) 0.7846(2) 0.22541(19) 0.0189(9) Uani 1 1 d . . . N12 N 0.9566(3) 0.8097(2) 0.18907(19) 0.0190(9) Uani 1 1 d . . . N13 N 1.1370(3) 0.7017(2) 0.23522(19) 0.0209(9) Uani 1 1 d . . . N14 N 1.1335(3) 0.5795(2) 0.32069(19) 0.0221(9) Uani 1 1 d . . . N15 N 0.9529(3) 0.5533(2) 0.3591(2) 0.0207(9) Uani 1 1 d . . . N16 N 0.7841(3) 0.6544(2) 0.31343(19) 0.0189(9) Uani 1 1 d . . . N17 N 0.9590(3) 0.6805(2) 0.27495(19) 0.0164(9) Uani 1 1 d . . . N18 N 0.6191(3) 0.7579(2) 0.2642(2) 0.0198(9) Uani 1 1 d . . . N19 N 1.1294(3) 0.8304(2) 0.1542(2) 0.0211(9) Uani 1 1 d . . . N20 N 1.1247(3) 0.4533(2) 0.4005(2) 0.0254(10) Uani 1 1 d . . . C27 C 0.7360(4) 0.7311(3) 0.2679(2) 0.0182(11) Uani 1 1 d . . . C28 C 0.9005(4) 0.7592(3) 0.2293(2) 0.0180(11) Uani 1 1 d . . . C29 C 1.0733(4) 0.7788(3) 0.1942(2) 0.0201(11) Uani 1 1 d . . . C30 C 1.0787(4) 0.6540(3) 0.2768(2) 0.0185(11) Uani 1 1 d . . . C31 C 1.0688(4) 0.5313(3) 0.3591(2) 0.0220(11) Uani 1 1 d . . . C32 C 0.8973(4) 0.6291(3) 0.3165(2) 0.0170(11) Uani 1 1 d . . . C33 C 0.5462(3) 0.7169(3) 0.3129(2) 0.0176(11) Uani 1 1 d . . . C34 C 0.5429(4) 0.7124(3) 0.3901(2) 0.0224(11) Uani 1 1 d . . . H34 H 0.5920 0.7336 0.4117 0.027 Uiso 1 1 calc R . . C35 C 0.4679(4) 0.6769(3) 0.4360(3) 0.0274(12) Uani 1 1 d . . . H35 H 0.4654 0.6736 0.4891 0.033 Uiso 1 1 calc R . . C36 C 0.3963(4) 0.6461(3) 0.4043(3) 0.0295(12) Uani 1 1 d . . . H36 H 0.3439 0.6228 0.4359 0.035 Uiso 1 1 calc R . . C37 C 0.4010(4) 0.6491(3) 0.3275(3) 0.0298(13) Uani 1 1 d . . . H37 H 0.3532 0.6266 0.3061 0.036 Uiso 1 1 calc R . . C38 C 0.4751(4) 0.6850(3) 0.2815(3) 0.0235(11) Uani 1 1 d . . . H38 H 0.4776 0.6878 0.2284 0.028 Uiso 1 1 calc R . . C39 C 0.5609(4) 0.8314(3) 0.2093(2) 0.0176(11) Uani 1 1 d . . . C40 C 0.4713(4) 0.9124(3) 0.2347(2) 0.0217(11) Uani 1 1 d . . . H40 H 0.4531 0.9222 0.2870 0.026 Uiso 1 1 calc R . . C41 C 0.4086(4) 0.9788(3) 0.1832(2) 0.0229(11) Uani 1 1 d . . . H41 H 0.3455 1.0336 0.2002 0.028 Uiso 1 1 calc R . . C42 C 0.4372(4) 0.9658(3) 0.1073(2) 0.0228(11) Uani 1 1 d . . . H42 H 0.3941 1.0119 0.0721 0.027 Uiso 1 1 calc R . . C43 C 0.5288(4) 0.8856(3) 0.0825(3) 0.0260(12) Uani 1 1 d . . . H43 H 0.5486 0.8766 0.0302 0.031 Uiso 1 1 calc R . . C44 C 0.5914(4) 0.8189(3) 0.1335(2) 0.0237(11) Uani 1 1 d . . . H44 H 0.6553 0.7644 0.1164 0.028 Uiso 1 1 calc R . . C45 C 1.0713(4) 0.9130(3) 0.1052(2) 0.0234(11) Uani 1 1 d . . . H45A H 1.0055 0.9051 0.0871 0.028 Uiso 1 1 calc R . . H45B H 1.1271 0.9173 0.0608 0.028 Uiso 1 1 calc R . . C46 C 1.0259(4) 1.0037(3) 0.1450(3) 0.0371(13) Uani 1 1 d . . . H46A H 0.9685 1.0008 0.1879 0.056 Uiso 1 1 calc R . . H46B H 0.9890 1.0570 0.1100 0.056 Uiso 1 1 calc R . . H46C H 1.0908 1.0121 0.1628 0.056 Uiso 1 1 calc R . . C47 C 1.2541(4) 0.8074(3) 0.1570(3) 0.0289(12) Uani 1 1 d . . . H47A H 1.2739 0.7798 0.2078 0.035 Uiso 1 1 calc R . . H47B H 1.2699 0.8660 0.1479 0.035 Uiso 1 1 calc R . . C48 C 1.3305(4) 0.7390(3) 0.0993(2) 0.0289(12) Uani 1 1 d . . . H48A H 1.3235 0.6779 0.1123 0.043 Uiso 1 1 calc R . . H48B H 1.4118 0.7316 0.0985 0.043 Uiso 1 1 calc R . . H48C H 1.3056 0.7632 0.0495 0.043 Uiso 1 1 calc R . . C49 C 1.2497(4) 0.4237(4) 0.4061(3) 0.0415(14) Uani 1 1 d . . . H49A H 1.2872 0.4483 0.3606 0.050 Uiso 1 1 calc R . . H49B H 1.2866 0.3541 0.4085 0.050 Uiso 1 1 calc R . . C50 C 1.2692(4) 0.4594(4) 0.4751(3) 0.0516(16) Uani 1 1 d . . . H50A H 1.2283 0.5280 0.4745 0.077 Uiso 1 1 calc R . . H50B H 1.3529 0.4433 0.4751 0.077 Uiso 1 1 calc R . . H50C H 1.2392 0.4301 0.5203 0.077 Uiso 1 1 calc R . . C51 C 1.0662(4) 0.3932(3) 0.4418(2) 0.0258(12) Uani 1 1 d . . . H51A H 0.9848 0.4328 0.4601 0.031 Uiso 1 1 calc R . . H51B H 1.1065 0.3609 0.4861 0.031 Uiso 1 1 calc R . . C52 C 1.0659(4) 0.3199(3) 0.3924(3) 0.0401(14) Uani 1 1 d . . . H52A H 1.0247 0.3518 0.3490 0.060 Uiso 1 1 calc R . . H52B H 1.0264 0.2809 0.4217 0.060 Uiso 1 1 calc R . . H52C H 1.1464 0.2800 0.3749 0.060 Uiso 1 1 calc R . . O1 O 0.6036(3) 0.3985(3) 0.3882(2) 0.0540(11) Uani 1 1 d . . . O2 O 0.7836(3) 0.3163(2) 0.3989(2) 0.0567(11) Uani 1 1 d . . . N21 N 0.7058(4) 0.3882(3) 0.3782(2) 0.0356(11) Uani 1 1 d . . . C53 C 0.7374(4) 0.4651(3) 0.3378(3) 0.0407(14) Uani 1 1 d . . . H53A H 0.7997 0.4711 0.3607 0.061 Uiso 1 1 calc R . . H53B H 0.6690 0.5243 0.3407 0.061 Uiso 1 1 calc R . . H53C H 0.7646 0.4512 0.2849 0.061 Uiso 1 1 calc R . . O3 O 0.7292(3) 0.5815(3) 0.1732(2) 0.0702(12) Uani 1 1 d . . . O4 O 0.7850(3) 0.5902(2) 0.0593(2) 0.0587(12) Uani 1 1 d . . . N22 N 0.7353(4) 0.5579(3) 0.1069(3) 0.0458(12) Uani 1 1 d . . . C54 C 0.6962(4) 0.4826(4) 0.1063(3) 0.0599(18) Uani 1 1 d . . . H54A H 0.7157 0.4593 0.0558 0.090 Uiso 1 1 calc R . . H54B H 0.6116 0.5055 0.1203 0.090 Uiso 1 1 calc R . . H54C H 0.7346 0.4314 0.1424 0.090 Uiso 1 1 calc R . . O5 O 0.1243(3) 0.6433(3) 0.0341(3) 0.0792(14) Uani 1 1 d . . . O6 O 0.1199(3) 0.7697(3) -0.0339(2) 0.0538(11) Uani 1 1 d . . . N23 N 0.0729(4) 0.7193(4) 0.0009(3) 0.0477(12) Uani 1 1 d . . . C55 C -0.0557(4) 0.7521(3) 0.0086(3) 0.0416(14) Uani 1 1 d . . . H55A H -0.0783 0.6980 0.0094 0.062 Uiso 1 1 calc R . . H55B H -0.0850 0.7962 -0.0340 0.062 Uiso 1 1 calc R . . H55C H -0.0891 0.7837 0.0556 0.062 Uiso 1 1 calc R . . O7 O 0.7785(3) -0.0260(2) 0.02424(19) 0.0495(10) Uani 1 1 d . . . O8 O 0.6398(3) 0.1065(2) 0.0480(2) 0.0589(11) Uani 1 1 d . . . N24 N 0.7107(4) 0.0296(3) 0.0677(2) 0.0331(10) Uani 1 1 d . . . C56 C 0.7094(4) 0.0057(3) 0.1484(2) 0.0312(12) Uani 1 1 d . . . H56A H 0.6372 -0.0038 0.1685 0.047 Uiso 1 1 calc R . . H56B H 0.7136 0.0570 0.1732 0.047 Uiso 1 1 calc R . . H56C H 0.7765 -0.0524 0.1577 0.047 Uiso 1 1 calc R . . O9 O 0.7720(3) 0.8209(2) 0.4162(2) 0.0509(11) Uani 1 1 d . . . O10 O 0.5939(3) 0.9052(2) 0.39827(19) 0.0467(10) Uani 1 1 d . . . N25 N 0.6982(4) 0.8907(3) 0.3903(2) 0.0308(10) Uani 1 1 d . . . C57 C 0.7353(4) 0.9632(3) 0.3453(3) 0.0307(12) Uani 1 1 d . . . H57A H 0.7882 0.9772 0.3720 0.046 Uiso 1 1 calc R . . H57B H 0.6666 1.0206 0.3378 0.046 Uiso 1 1 calc R . . H57C H 0.7755 0.9396 0.2964 0.046 Uiso 1 1 calc R . . 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 N1 0.010(2) 0.016(2) 0.029(2) -0.0009(18) -0.0014(17) -0.0022(18) N2 0.017(2) 0.017(2) 0.027(2) -0.0031(19) -0.0029(18) -0.0077(19) N3 0.015(2) 0.024(2) 0.026(2) -0.0004(19) 0.0009(18) -0.008(2) N4 0.014(2) 0.021(2) 0.022(2) -0.0008(19) 0.0025(17) -0.0039(19) N5 0.016(2) 0.015(2) 0.023(2) 0.0019(18) -0.0022(17) 0.0001(18) N6 0.014(2) 0.016(2) 0.027(2) 0.0036(18) -0.0021(17) -0.0035(18) N7 0.011(2) 0.020(2) 0.022(2) -0.0002(18) 0.0002(17) -0.0064(18) N8 0.013(2) 0.022(2) 0.022(2) 0.0105(18) -0.0027(17) -0.0079(18) N9 0.015(2) 0.020(2) 0.023(2) -0.0003(18) -0.0001(17) -0.0069(19) N10 0.017(2) 0.026(2) 0.027(2) 0.006(2) -0.0012(18) -0.001(2) C1 0.016(3) 0.018(3) 0.025(3) -0.001(2) -0.001(2) -0.008(2) C2 0.020(3) 0.012(3) 0.016(3) 0.004(2) -0.003(2) -0.005(2) C3 0.020(3) 0.023(3) 0.012(2) -0.007(2) 0.007(2) -0.014(2) C4 0.015(3) 0.025(3) 0.020(3) -0.010(2) 0.001(2) -0.007(2) C5 0.020(3) 0.020(3) 0.014(3) -0.005(2) 0.002(2) 0.001(2) C6 0.016(3) 0.013(3) 0.021(3) -0.001(2) 0.007(2) -0.008(2) C7 0.014(3) 0.011(2) 0.026(3) 0.000(2) -0.001(2) 0.000(2) C8 0.016(3) 0.018(3) 0.029(3) 0.001(2) 0.002(2) -0.009(2) C9 0.021(3) 0.023(3) 0.025(3) 0.004(2) 0.001(2) -0.003(2) C10 0.024(3) 0.021(3) 0.032(3) 0.004(2) 0.005(2) -0.009(2) C11 0.016(3) 0.024(3) 0.037(3) -0.002(3) 0.003(2) -0.009(2) C12 0.024(3) 0.020(3) 0.021(3) -0.001(2) -0.005(2) -0.007(2) C13 0.012(3) 0.023(3) 0.014(3) 0.001(2) -0.001(2) -0.007(2) C14 0.020(3) 0.018(3) 0.031(3) -0.004(2) -0.001(2) -0.003(2) C15 0.034(3) 0.024(3) 0.013(3) -0.001(2) 0.001(2) -0.012(2) C16 0.030(3) 0.018(3) 0.030(3) 0.001(2) -0.010(2) -0.011(2) C17 0.019(3) 0.022(3) 0.027(3) 0.005(2) 0.000(2) -0.008(2) C18 0.021(3) 0.022(3) 0.017(3) -0.002(2) 0.001(2) -0.008(2) C19 0.023(3) 0.024(3) 0.025(3) 0.002(2) 0.003(2) -0.011(2) C20 0.039(3) 0.026(3) 0.040(3) -0.002(3) -0.002(2) -0.013(3) C21 0.013(3) 0.038(3) 0.030(3) 0.001(3) 0.000(2) -0.013(2) C22 0.019(3) 0.036(3) 0.036(3) 0.001(3) 0.004(2) -0.010(2) C23 0.016(3) 0.034(3) 0.044(3) 0.015(3) 0.002(2) 0.000(2) C24 0.027(3) 0.038(3) 0.053(4) 0.008(3) -0.010(3) -0.015(3) C25 0.019(3) 0.027(3) 0.028(3) 0.003(2) -0.002(2) -0.002(2) C26 0.031(3) 0.029(3) 0.054(4) -0.010(3) -0.009(3) -0.007(3) N11 0.018(2) 0.016(2) 0.023(2) 0.0016(18) -0.0034(17) -0.0073(19) N12 0.016(2) 0.020(2) 0.021(2) 0.0025(18) -0.0010(17) -0.0090(19) N13 0.018(2) 0.022(2) 0.021(2) 0.0035(19) 0.0001(18) -0.008(2) N14 0.016(2) 0.029(2) 0.017(2) 0.0031(19) 0.0006(17) -0.006(2) N15 0.016(2) 0.015(2) 0.028(2) 0.0018(18) -0.0027(18) -0.0027(18) N16 0.014(2) 0.017(2) 0.021(2) 0.0025(18) -0.0045(17) -0.0024(18) N17 0.015(2) 0.014(2) 0.018(2) 0.0010(17) -0.0047(17) -0.0028(18) N18 0.012(2) 0.018(2) 0.028(2) 0.0072(18) -0.0040(17) -0.0062(18) N19 0.016(2) 0.025(2) 0.025(2) 0.0013(19) -0.0018(18) -0.0119(19) N20 0.016(2) 0.023(2) 0.025(2) 0.0040(19) 0.0027(18) 0.0019(19) C27 0.023(3) 0.017(3) 0.017(3) -0.004(2) -0.005(2) -0.009(2) C28 0.014(3) 0.020(3) 0.017(3) -0.004(2) 0.000(2) -0.003(2) C29 0.019(3) 0.021(3) 0.020(3) -0.008(2) -0.002(2) -0.006(2) C30 0.013(3) 0.020(3) 0.016(3) -0.005(2) -0.004(2) 0.002(2) C31 0.024(3) 0.015(3) 0.018(3) -0.001(2) -0.003(2) 0.001(2) C32 0.019(3) 0.018(3) 0.012(3) -0.003(2) 0.002(2) -0.006(2) C33 0.010(3) 0.013(3) 0.026(3) 0.004(2) -0.001(2) -0.003(2) C34 0.020(3) 0.018(3) 0.027(3) 0.002(2) -0.002(2) -0.007(2) C35 0.025(3) 0.023(3) 0.027(3) 0.004(2) 0.002(2) -0.006(2) C36 0.016(3) 0.021(3) 0.048(4) 0.006(3) 0.005(2) -0.009(2) C37 0.024(3) 0.027(3) 0.043(4) -0.001(3) -0.003(3) -0.015(3) C38 0.019(3) 0.021(3) 0.028(3) -0.002(2) -0.002(2) -0.006(2) C39 0.017(3) 0.013(3) 0.022(3) 0.008(2) -0.005(2) -0.006(2) C40 0.017(3) 0.023(3) 0.021(3) 0.001(2) 0.001(2) -0.006(2) C41 0.016(3) 0.017(3) 0.030(3) 0.001(2) -0.003(2) -0.002(2) C42 0.030(3) 0.015(3) 0.024(3) 0.005(2) -0.009(2) -0.008(2) C43 0.030(3) 0.025(3) 0.018(3) 0.003(2) -0.001(2) -0.008(2) C44 0.016(3) 0.018(3) 0.030(3) -0.002(2) 0.003(2) -0.001(2) C45 0.028(3) 0.022(3) 0.023(3) 0.000(2) 0.001(2) -0.013(2) C46 0.042(3) 0.026(3) 0.047(3) 0.001(3) -0.006(3) -0.016(3) C47 0.022(3) 0.035(3) 0.034(3) 0.002(3) -0.001(2) -0.018(3) C48 0.022(3) 0.029(3) 0.031(3) 0.006(2) -0.002(2) -0.008(2) C49 0.023(3) 0.048(3) 0.027(3) 0.023(3) 0.004(2) 0.004(3) C50 0.032(3) 0.053(4) 0.074(5) 0.027(3) -0.021(3) -0.025(3) C51 0.026(3) 0.019(3) 0.027(3) 0.003(2) -0.004(2) -0.003(2) C52 0.041(3) 0.027(3) 0.045(3) -0.005(3) -0.008(3) -0.004(3) O1 0.060(3) 0.058(3) 0.057(3) 0.007(2) 0.003(2) -0.043(2) O2 0.080(3) 0.028(2) 0.059(3) 0.005(2) -0.019(2) -0.015(2) N21 0.050(3) 0.025(3) 0.031(3) -0.002(2) -0.001(2) -0.015(3) C53 0.055(4) 0.024(3) 0.047(4) 0.001(3) 0.009(3) -0.026(3) O3 0.082(3) 0.057(3) 0.061(3) -0.004(2) 0.002(2) -0.019(2) O4 0.065(3) 0.042(2) 0.060(3) 0.006(2) 0.030(2) -0.027(2) N22 0.049(3) 0.033(3) 0.039(3) -0.015(2) 0.029(2) -0.007(2) C54 0.048(4) 0.037(3) 0.095(5) 0.011(3) -0.001(3) -0.025(3) O5 0.057(3) 0.056(3) 0.115(4) 0.025(3) -0.025(3) -0.014(2) O6 0.067(3) 0.060(3) 0.047(3) -0.002(2) 0.004(2) -0.043(2) N23 0.047(4) 0.041(3) 0.047(3) -0.012(3) -0.013(2) -0.003(3) C55 0.035(3) 0.036(3) 0.051(4) -0.013(3) -0.011(3) -0.005(3) O7 0.049(3) 0.046(2) 0.039(2) -0.008(2) 0.0092(19) -0.007(2) O8 0.078(3) 0.032(2) 0.062(3) 0.012(2) -0.035(2) -0.009(2) N24 0.030(3) 0.025(3) 0.044(3) 0.009(2) -0.013(2) -0.011(2) C56 0.036(3) 0.025(3) 0.026(3) 0.008(2) -0.004(2) -0.008(2) O9 0.068(3) 0.026(2) 0.053(3) 0.0130(19) -0.016(2) -0.012(2) O10 0.049(3) 0.051(2) 0.051(3) 0.0106(19) -0.003(2) -0.035(2) N25 0.044(3) 0.026(3) 0.027(3) 0.003(2) -0.002(2) -0.021(3) C57 0.038(3) 0.023(3) 0.030(3) 0.006(2) 0.001(2) -0.015(3) _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 N1 C2 1.335(5) . ? N1 C1 1.341(5) . ? N2 C2 1.331(5) . ? N2 C3 1.365(5) . ? N3 C4 1.324(5) . ? N3 C3 1.363(5) . ? N4 C4 1.317(5) . ? N4 C5 1.344(5) . ? N5 C6 1.312(5) . ? N5 C5 1.363(5) . ? N6 C6 1.339(5) . ? N6 C1 1.339(5) . ? N7 C2 1.394(5) . ? N7 C6 1.400(5) . ? N7 C4 1.407(5) . ? N8 C1 1.365(5) . ? N8 C13 1.442(5) . ? N8 C7 1.446(5) . ? N9 C3 1.333(5) . ? N9 C19 1.466(5) . ? N9 C21 1.480(5) . ? N10 C5 1.338(5) . ? N10 C25 1.474(5) . ? N10 C23 1.477(5) . ? C7 C12 1.380(5) . ? C7 C8 1.383(6) . ? C8 C9 1.385(5) . ? C8 H8 0.9500 . ? C9 C10 1.379(6) . ? C9 H9 0.9500 . ? C10 C11 1.382(6) . ? C10 H10 0.9500 . ? C11 C12 1.393(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.371(6) . ? C13 C18 1.390(5) . ? C14 C15 1.372(5) . ? C14 H14 0.9500 . ? C15 C16 1.395(5) . ? C15 H15 0.9500 . ? C16 C17 1.384(6) . ? C16 H16 0.9500 . ? C17 C18 1.396(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.518(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.515(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.511(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.517(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N11 C28 1.327(5) . ? N11 C27 1.340(5) . ? N12 C28 1.327(5) . ? N12 C29 1.368(5) . ? N13 C30 1.325(5) . ? N13 C29 1.356(5) . ? N14 C30 1.327(5) . ? N14 C31 1.365(5) . ? N15 C32 1.328(5) . ? N15 C31 1.359(5) . ? N16 C32 1.327(5) . ? N16 C27 1.344(5) . ? N17 C32 1.394(5) . ? N17 C28 1.397(5) . ? N17 C30 1.399(5) . ? N18 C27 1.372(5) . ? N18 C33 1.439(5) . ? N18 C39 1.454(5) . ? N19 C29 1.338(5) . ? N19 C45 1.467(5) . ? N19 C47 1.471(5) . ? N20 C31 1.338(5) . ? N20 C51 1.465(5) . ? N20 C49 1.471(5) . ? C33 C34 1.382(6) . ? C33 C38 1.392(5) . ? C34 C35 1.385(6) . ? C34 H34 0.9500 . ? C35 C36 1.387(6) . ? C35 H35 0.9500 . ? C36 C37 1.374(6) . ? C36 H36 0.9500 . ? C37 C38 1.381(6) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C44 1.377(6) . ? C39 C40 1.386(5) . ? C40 C41 1.381(5) . ? C40 H40 0.9500 . ? C41 C42 1.379(6) . ? C41 H41 0.9500 . ? C42 C43 1.385(5) . ? C42 H42 0.9500 . ? C43 C44 1.377(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.516(5) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 C48 1.510(5) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.511(6) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.526(6) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? O1 N21 1.215(5) . ? O2 N21 1.223(5) . ? N21 C53 1.473(5) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? O3 N22 1.275(5) . ? O4 N22 1.159(5) . ? N22 C54 1.431(6) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? O5 N23 1.230(5) . ? O6 N23 1.214(5) . ? N23 C55 1.480(6) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? O7 N24 1.208(5) . ? O8 N24 1.225(4) . ? N24 C56 1.457(5) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? O9 N25 1.215(4) . ? O10 N25 1.225(4) . ? N25 C57 1.482(5) . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 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 C2 N1 C1 115.8(4) . . ? C2 N2 C3 116.0(4) . . ? C4 N3 C3 117.0(4) . . ? C4 N4 C5 117.2(4) . . ? C6 N5 C5 115.7(4) . . ? C6 N6 C1 117.1(4) . . ? C2 N7 C6 120.7(4) . . ? C2 N7 C4 120.8(4) . . ? C6 N7 C4 118.6(4) . . ? C1 N8 C13 122.5(4) . . ? C1 N8 C7 121.3(4) . . ? C13 N8 C7 116.0(3) . . ? C3 N9 C19 122.5(4) . . ? C3 N9 C21 121.1(4) . . ? C19 N9 C21 116.3(3) . . ? C5 N10 C25 123.1(4) . . ? C5 N10 C23 121.2(4) . . ? C25 N10 C23 115.6(4) . . ? N6 C1 N1 127.9(4) . . ? N6 C1 N8 116.6(4) . . ? N1 C1 N8 115.5(4) . . ? N2 C2 N1 119.8(4) . . ? N2 C2 N7 120.1(4) . . ? N1 C2 N7 120.0(4) . . ? N9 C3 N3 117.3(4) . . ? N9 C3 N2 116.0(4) . . ? N3 C3 N2 126.7(4) . . ? N4 C4 N3 120.7(4) . . ? N4 C4 N7 120.1(4) . . ? N3 C4 N7 119.1(4) . . ? N10 C5 N4 117.5(4) . . ? N10 C5 N5 115.7(4) . . ? N4 C5 N5 126.7(4) . . ? N5 C6 N6 120.0(4) . . ? N5 C6 N7 121.6(4) . . ? N6 C6 N7 118.4(4) . . ? C12 C7 C8 119.9(4) . . ? C12 C7 N8 119.1(4) . . ? C8 C7 N8 120.9(4) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.5(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.3(4) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C7 C12 C11 120.3(4) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C18 120.5(4) . . ? C14 C13 N8 121.3(4) . . ? C18 C13 N8 118.1(4) . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.3(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.3(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C13 C18 C17 119.5(4) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N9 C19 C20 111.1(4) . . ? N9 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N9 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N9 C21 C22 111.4(3) . . ? N9 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? N9 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N10 C23 C24 112.6(4) . . ? N10 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? N10 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N10 C25 C26 111.6(4) . . ? N10 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? N10 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 N11 C27 115.8(4) . . ? C28 N12 C29 116.1(4) . . ? C30 N13 C29 116.2(4) . . ? C30 N14 C31 116.8(4) . . ? C32 N15 C31 116.4(4) . . ? C32 N16 C27 115.2(4) . . ? C32 N17 C28 119.2(4) . . ? C32 N17 C30 121.5(4) . . ? C28 N17 C30 119.2(4) . . ? C27 N18 C33 123.5(4) . . ? C27 N18 C39 120.8(4) . . ? C33 N18 C39 115.7(3) . . ? C29 N19 C45 122.5(4) . . ? C29 N19 C47 121.7(4) . . ? C45 N19 C47 115.8(3) . . ? C31 N20 C51 122.6(4) . . ? C31 N20 C49 120.7(4) . . ? C51 N20 C49 116.7(4) . . ? N11 C27 N16 128.5(4) . . ? N11 C27 N18 115.6(4) . . ? N16 C27 N18 115.8(4) . . ? N12 C28 N11 118.9(4) . . ? N12 C28 N17 120.8(4) . . ? N11 C28 N17 120.3(4) . . ? N19 C29 N13 117.3(4) . . ? N19 C29 N12 116.0(4) . . ? N13 C29 N12 126.7(4) . . ? N13 C30 N14 120.2(4) . . ? N13 C30 N17 120.9(4) . . ? N14 C30 N17 118.9(4) . . ? N20 C31 N15 115.9(4) . . ? N20 C31 N14 117.3(4) . . ? N15 C31 N14 126.8(4) . . ? N16 C32 N15 119.6(4) . . ? N16 C32 N17 120.9(4) . . ? N15 C32 N17 119.5(4) . . ? C34 C33 C38 120.0(4) . . ? C34 C33 N18 120.8(4) . . ? C38 C33 N18 119.2(4) . . ? C33 C34 C35 119.7(4) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 120.0(4) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C37 C36 C35 120.2(4) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C38 120.1(4) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C37 C38 C33 119.9(4) . . ? C37 C38 H38 120.0 . . ? C33 C38 H38 120.0 . . ? C44 C39 C40 120.7(4) . . ? C44 C39 N18 120.5(4) . . ? C40 C39 N18 118.7(4) . . ? C41 C40 C39 119.1(4) . . ? C41 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? C42 C41 C40 120.4(4) . . ? C42 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C41 C42 C43 119.9(4) . . ? C41 C42 H42 120.1 . . ? C43 C42 H42 120.1 . . ? C44 C43 C42 120.1(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C39 C44 C43 119.7(4) . . ? C39 C44 H44 120.2 . . ? C43 C44 H44 120.2 . . ? N19 C45 C46 112.3(4) . . ? N19 C45 H45A 109.1 . . ? C46 C45 H45A 109.1 . . ? N19 C45 H45B 109.1 . . ? C46 C45 H45B 109.1 . . ? H45A C45 H45B 107.9 . . ? 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 . . ? N19 C47 C48 111.9(3) . . ? N19 C47 H47A 109.2 . . ? C48 C47 H47A 109.2 . . ? N19 C47 H47B 109.2 . . ? C48 C47 H47B 109.2 . . ? H47A C47 H47B 107.9 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? N20 C49 C50 111.3(4) . . ? N20 C49 H49A 109.4 . . ? C50 C49 H49A 109.4 . . ? N20 C49 H49B 109.4 . . ? C50 C49 H49B 109.4 . . ? H49A C49 H49B 108.0 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? N20 C51 C52 111.6(4) . . ? N20 C51 H51A 109.3 . . ? C52 C51 H51A 109.3 . . ? N20 C51 H51B 109.3 . . ? C52 C51 H51B 109.3 . . ? H51A C51 H51B 108.0 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O1 N21 O2 123.1(5) . . ? O1 N21 C53 118.3(4) . . ? O2 N21 C53 118.7(5) . . ? N21 C53 H53A 109.5 . . ? N21 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? N21 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? O4 N22 O3 116.3(5) . . ? O4 N22 C54 130.3(5) . . ? O3 N22 C54 112.5(5) . . ? N22 C54 H54A 109.5 . . ? N22 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? N22 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O6 N23 O5 124.6(5) . . ? O6 N23 C55 119.0(5) . . ? O5 N23 C55 116.3(5) . . ? N23 C55 H55A 109.5 . . ? N23 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? N23 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O7 N24 O8 123.7(4) . . ? O7 N24 C56 119.7(4) . . ? O8 N24 C56 116.6(4) . . ? N24 C56 H56A 109.5 . . ? N24 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? N24 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? O9 N25 O10 124.2(4) . . ? O9 N25 C57 118.6(4) . . ? O10 N25 C57 117.1(4) . . ? N25 C57 H57A 109.5 . . ? N25 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? N25 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? 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 N6 C1 N1 3.2(7) . . . . ? C6 N6 C1 N8 -177.8(4) . . . . ? C2 N1 C1 N6 -0.1(6) . . . . ? C2 N1 C1 N8 -179.1(3) . . . . ? C13 N8 C1 N6 -170.6(4) . . . . ? C7 N8 C1 N6 15.6(6) . . . . ? C13 N8 C1 N1 8.5(6) . . . . ? C7 N8 C1 N1 -165.3(4) . . . . ? C3 N2 C2 N1 -178.9(4) . . . . ? C3 N2 C2 N7 2.8(5) . . . . ? C1 N1 C2 N2 -179.9(4) . . . . ? C1 N1 C2 N7 -1.6(6) . . . . ? C6 N7 C2 N2 178.4(4) . . . . ? C4 N7 C2 N2 -2.8(6) . . . . ? C6 N7 C2 N1 0.2(6) . . . . ? C4 N7 C2 N1 179.0(4) . . . . ? C19 N9 C3 N3 -176.6(4) . . . . ? C21 N9 C3 N3 -0.6(6) . . . . ? C19 N9 C3 N2 4.8(6) . . . . ? C21 N9 C3 N2 -179.2(3) . . . . ? C4 N3 C3 N9 176.1(4) . . . . ? C4 N3 C3 N2 -5.5(6) . . . . ? C2 N2 C3 N9 179.8(4) . . . . ? C2 N2 C3 N3 1.3(6) . . . . ? C5 N4 C4 N3 -179.6(4) . . . . ? C5 N4 C4 N7 -0.5(6) . . . . ? C3 N3 C4 N4 -175.6(4) . . . . ? C3 N3 C4 N7 5.3(6) . . . . ? C2 N7 C4 N4 179.4(4) . . . . ? C6 N7 C4 N4 -1.8(6) . . . . ? C2 N7 C4 N3 -1.5(6) . . . . ? C6 N7 C4 N3 177.3(4) . . . . ? C25 N10 C5 N4 -179.9(4) . . . . ? C23 N10 C5 N4 -2.1(6) . . . . ? C25 N10 C5 N5 -0.5(6) . . . . ? C23 N10 C5 N5 177.2(4) . . . . ? C4 N4 C5 N10 -178.5(4) . . . . ? C4 N4 C5 N5 2.2(6) . . . . ? C6 N5 C5 N10 179.4(4) . . . . ? C6 N5 C5 N4 -1.3(6) . . . . ? C5 N5 C6 N6 177.3(4) . . . . ? C5 N5 C6 N7 -1.3(6) . . . . ? C1 N6 C6 N5 176.9(4) . . . . ? C1 N6 C6 N7 -4.4(6) . . . . ? C2 N7 C6 N5 -178.4(4) . . . . ? C4 N7 C6 N5 2.8(6) . . . . ? C2 N7 C6 N6 3.0(6) . . . . ? C4 N7 C6 N6 -175.8(3) . . . . ? C1 N8 C7 C12 -132.8(4) . . . . ? C13 N8 C7 C12 53.0(5) . . . . ? C1 N8 C7 C8 50.3(6) . . . . ? C13 N8 C7 C8 -123.8(4) . . . . ? C12 C7 C8 C9 0.6(6) . . . . ? N8 C7 C8 C9 177.5(4) . . . . ? C7 C8 C9 C10 -1.8(6) . . . . ? C8 C9 C10 C11 1.9(7) . . . . ? C9 C10 C11 C12 -0.9(7) . . . . ? C8 C7 C12 C11 0.4(6) . . . . ? N8 C7 C12 C11 -176.5(4) . . . . ? C10 C11 C12 C7 -0.2(6) . . . . ? C1 N8 C13 C14 70.3(5) . . . . ? C7 N8 C13 C14 -115.6(4) . . . . ? C1 N8 C13 C18 -113.6(4) . . . . ? C7 N8 C13 C18 60.5(5) . . . . ? C18 C13 C14 C15 -2.3(7) . . . . ? N8 C13 C14 C15 173.6(4) . . . . ? C13 C14 C15 C16 0.3(7) . . . . ? C14 C15 C16 C17 1.6(6) . . . . ? C15 C16 C17 C18 -1.5(6) . . . . ? C14 C13 C18 C17 2.4(6) . . . . ? N8 C13 C18 C17 -173.7(4) . . . . ? C16 C17 C18 C13 -0.5(6) . . . . ? C3 N9 C19 C20 89.8(5) . . . . ? C21 N9 C19 C20 -86.4(4) . . . . ? C3 N9 C21 C22 87.3(5) . . . . ? C19 N9 C21 C22 -96.4(4) . . . . ? C5 N10 C23 C24 99.3(5) . . . . ? C25 N10 C23 C24 -82.8(5) . . . . ? C5 N10 C25 C26 88.0(5) . . . . ? C23 N10 C25 C26 -89.9(4) . . . . ? C28 N11 C27 N16 -0.8(6) . . . . ? C28 N11 C27 N18 179.5(3) . . . . ? C32 N16 C27 N11 0.3(6) . . . . ? C32 N16 C27 N18 180.0(3) . . . . ? C33 N18 C27 N11 -171.6(4) . . . . ? C39 N18 C27 N11 8.4(5) . . . . ? C33 N18 C27 N16 8.7(6) . . . . ? C39 N18 C27 N16 -171.3(4) . . . . ? C29 N12 C28 N11 -178.6(4) . . . . ? C29 N12 C28 N17 1.2(5) . . . . ? C27 N11 C28 N12 -179.5(4) . . . . ? C27 N11 C28 N17 0.7(5) . . . . ? C32 N17 C28 N12 180.0(4) . . . . ? C30 N17 C28 N12 -1.3(6) . . . . ? C32 N17 C28 N11 -0.2(6) . . . . ? C30 N17 C28 N11 178.6(4) . . . . ? C45 N19 C29 N13 177.3(4) . . . . ? C47 N19 C29 N13 -2.8(6) . . . . ? C45 N19 C29 N12 -2.4(6) . . . . ? C47 N19 C29 N12 177.5(3) . . . . ? C30 N13 C29 N19 177.3(4) . . . . ? C30 N13 C29 N12 -3.0(6) . . . . ? C28 N12 C29 N19 -179.3(4) . . . . ? C28 N12 C29 N13 1.0(6) . . . . ? C29 N13 C30 N14 -177.6(4) . . . . ? C29 N13 C30 N17 2.8(6) . . . . ? C31 N14 C30 N13 -177.0(4) . . . . ? C31 N14 C30 N17 2.7(5) . . . . ? C32 N17 C30 N13 177.9(4) . . . . ? C28 N17 C30 N13 -0.8(5) . . . . ? C32 N17 C30 N14 -1.8(6) . . . . ? C28 N17 C30 N14 179.5(4) . . . . ? C51 N20 C31 N15 1.7(6) . . . . ? C49 N20 C31 N15 -178.6(4) . . . . ? C51 N20 C31 N14 -177.4(4) . . . . ? C49 N20 C31 N14 2.3(6) . . . . ? C32 N15 C31 N20 -178.2(4) . . . . ? C32 N15 C31 N14 0.8(6) . . . . ? C30 N14 C31 N20 176.6(4) . . . . ? C30 N14 C31 N15 -2.4(6) . . . . ? C27 N16 C32 N15 -179.0(4) . . . . ? C27 N16 C32 N17 0.3(5) . . . . ? C31 N15 C32 N16 179.5(4) . . . . ? C31 N15 C32 N17 0.3(6) . . . . ? C28 N17 C32 N16 -0.3(6) . . . . ? C30 N17 C32 N16 -179.0(3) . . . . ? C28 N17 C32 N15 178.9(4) . . . . ? C30 N17 C32 N15 0.2(6) . . . . ? C27 N18 C33 C34 52.9(6) . . . . ? C39 N18 C33 C34 -127.1(4) . . . . ? C27 N18 C33 C38 -129.7(4) . . . . ? C39 N18 C33 C38 50.4(5) . . . . ? C38 C33 C34 C35 -0.6(6) . . . . ? N18 C33 C34 C35 176.8(4) . . . . ? C33 C34 C35 C36 -0.1(6) . . . . ? C34 C35 C36 C37 1.1(7) . . . . ? C35 C36 C37 C38 -1.5(7) . . . . ? C36 C37 C38 C33 0.8(7) . . . . ? C34 C33 C38 C37 0.3(6) . . . . ? N18 C33 C38 C37 -177.2(4) . . . . ? C27 N18 C39 C44 63.8(5) . . . . ? C33 N18 C39 C44 -116.2(4) . . . . ? C27 N18 C39 C40 -118.8(4) . . . . ? C33 N18 C39 C40 61.2(5) . . . . ? C44 C39 C40 C41 3.2(6) . . . . ? N18 C39 C40 C41 -174.2(4) . . . . ? C39 C40 C41 C42 -1.9(6) . . . . ? C40 C41 C42 C43 0.3(7) . . . . ? C41 C42 C43 C44 0.0(7) . . . . ? C40 C39 C44 C43 -2.9(7) . . . . ? N18 C39 C44 C43 174.5(4) . . . . ? C42 C43 C44 C39 1.3(7) . . . . ? C29 N19 C45 C46 93.1(5) . . . . ? C47 N19 C45 C46 -86.8(4) . . . . ? C29 N19 C47 C48 88.5(5) . . . . ? C45 N19 C47 C48 -91.6(4) . . . . ? C31 N20 C49 C50 94.8(5) . . . . ? C51 N20 C49 C50 -85.6(5) . . . . ? C31 N20 C51 C52 86.9(5) . . . . ? C49 N20 C51 C52 -92.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C56 H56C N11 0.98 2.63 3.352(5) 131.0 1_545 C56 H56C N12 0.98 2.52 3.491(5) 173.6 1_545 C57 H57A N5 0.98 2.59 3.407(5) 140.8 1_565 C45 H45B O7 0.99 2.63 3.497(5) 146.0 2_765 C22 H22C O4 0.98 2.63 3.567(6) 160.4 2_765 C19 H19B O4 0.99 2.47 3.387(6) 153.2 2_765 C54 H54A O5 0.98 2.51 3.352(7) 144.5 2_665 C9 H9 O10 0.95 2.52 3.312(6) 141.4 2_666 C35 H35 O1 0.95 2.54 3.354(6) 144.0 2_666 C55 H55C N12 0.98 2.68 3.522(6) 144.9 1_455 C8 H8 O1 0.95 2.62 3.330(5) 131.9 . C54 H54C N1 0.98 2.40 3.329(6) 158.6 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.870 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.065 data_ansc127_0m _database_code_depnum_ccdc_archive 'CCDC 804317' #TrackingRef 'ansc127-0m-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,5-Diphenylamino-8-ethylamino-tri-s-triazine ; _chemical_name_common 1,5-Diphenylamino-8-ethylamino-tri-s-triazine _chemical_formula_moiety 'C34 H30 N10, 2(H2O)' _chemical_formula_sum 'C34 H34 N10 O2' _chemical_formula_weight 614.71 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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 12.5928(7) _cell_length_b 12.5928(7) _cell_length_c 19.4047(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3077.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 901 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 20.30 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.088 _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 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11538 _diffrn_reflns_av_R_equivalents 0.1571 _diffrn_reflns_av_sigmaI/netI 0.1876 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3036 _reflns_number_gt 1154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2007)' _computing_cell_refinement 'Bruker SMART (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 2007)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2007)' _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. PROBLEM: Ratio Observed / Unique Reflections too Low .... 38 Perc. RESPONSE: The diffraction power of the crystal was very poor, i.e., it has shown no reflections beyond 50 deg. 2Theta. Cut-off at lower angle would increase the obsd/unique ratio, but on the expense of bond precision. The water molecule is disordered in two positions (50:50) including DFIX restraints on O-H bonds, and SADI restraints on the geometry. ; _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^)+(0.0707P)^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 3036 _refine_ls_number_parameters 232 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.2683 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 0.808 _refine_ls_restrained_S_all 0.807 _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 N1 N 0.7007(3) -0.0346(3) -0.0017(2) 0.0245(10) Uani 1 1 d . . . N2 N 0.8867(3) 0.0164(3) -0.0007(2) 0.0264(10) Uani 1 1 d . . . N3 N 0.8354(3) -0.1646(3) 0.0000 0.0217(13) Uani 1 2 d S . . N4 N 0.6532(3) -0.2104(3) 0.00376(19) 0.0240(9) Uani 1 1 d . . . N5 N 0.6123(3) -0.3877(3) 0.0000 0.0272(14) Uani 1 2 d S . . N6 N 0.7522(3) 0.1393(3) -0.0074(2) 0.0264(10) Uani 1 1 d . . . C1 C 0.7282(3) -0.1365(4) 0.0007(2) 0.0237(11) Uani 1 1 d . . . C2 C 0.7813(4) 0.0359(4) -0.0031(2) 0.0272(12) Uani 1 1 d . . . C3 C 0.9146(3) -0.0854(3) 0.0000 0.0244(16) Uani 1 2 d S . . C4 C 0.6865(4) -0.3135(4) 0.0000 0.0254(17) Uani 1 2 d S . . C5 C 0.6392(4) -0.5008(3) -0.0036(2) 0.0295(11) Uani 1 1 d . . . H5A H 0.5875 -0.5420 0.0240 0.035 Uiso 1 1 calc R . . H5B H 0.7106 -0.5121 0.0163 0.035 Uiso 1 1 calc R . . C6 C 0.6380(4) -0.5403(4) -0.0770(2) 0.0394(14) Uani 1 1 d . . . H6A H 0.5697 -0.5227 -0.0984 0.059 Uiso 1 1 calc R . . H6B H 0.6479 -0.6175 -0.0774 0.059 Uiso 1 1 calc R . . H6C H 0.6955 -0.5065 -0.1030 0.059 Uiso 1 1 calc R . . C7 C 0.6407(4) 0.1691(3) -0.0173(3) 0.0260(12) Uani 1 1 d . . . C8 C 0.5890(4) 0.1433(4) -0.0776(3) 0.0307(12) Uani 1 1 d . . . H8 H 0.6244 0.1047 -0.1128 0.037 Uiso 1 1 calc R . . C9 C 0.4850(4) 0.1747(4) -0.0860(3) 0.0330(13) Uani 1 1 d . . . H9 H 0.4480 0.1565 -0.1270 0.040 Uiso 1 1 calc R . . C10 C 0.4337(4) 0.2324(4) -0.0353(3) 0.0369(14) Uani 1 1 d . . . H10 H 0.3619 0.2535 -0.0418 0.044 Uiso 1 1 calc R . . C11 C 0.4861(4) 0.2596(3) 0.0248(3) 0.0315(13) Uani 1 1 d . . . H11 H 0.4508 0.2994 0.0595 0.038 Uiso 1 1 calc R . . C12 C 0.5913(4) 0.2279(4) 0.0338(2) 0.0289(12) Uani 1 1 d . . . H12 H 0.6286 0.2465 0.0746 0.035 Uiso 1 1 calc R . . C13 C 0.8276(3) 0.2242(3) -0.0122(3) 0.0262(12) Uani 1 1 d . . . C14 C 0.8671(4) 0.2710(4) 0.0462(3) 0.0373(14) Uani 1 1 d . . . H14 H 0.8489 0.2439 0.0903 0.045 Uiso 1 1 calc R . . C15 C 0.9350(4) 0.3597(4) 0.0404(3) 0.0447(15) Uani 1 1 d . . . H15 H 0.9641 0.3916 0.0806 0.054 Uiso 1 1 calc R . . C16 C 0.9588(4) 0.3999(4) -0.0235(3) 0.0422(15) Uani 1 1 d . . . H16 H 1.0027 0.4609 -0.0274 0.051 Uiso 1 1 calc R . . C17 C 0.9191(4) 0.3516(4) -0.0824(3) 0.0417(14) Uani 1 1 d . . . H17 H 0.9365 0.3792 -0.1266 0.050 Uiso 1 1 calc R . . C18 C 0.8533(4) 0.2622(4) -0.0767(3) 0.0377(14) Uani 1 1 d . . . H18 H 0.8267 0.2282 -0.1169 0.045 Uiso 1 1 calc R . . O1A O 0.5950(6) 0.3944(7) 0.1956(4) 0.068(2) Uani 0.50 1 d PD A 1 H1A1 H 0.639(3) 0.368(10) 0.238(3) 0.082 Uiso 0.50 1 d PD B 1 H1A2 H 0.517(2) 0.408(8) 0.212(3) 0.082 Uiso 0.50 1 d PD C 1 O1B O 0.6645(7) 0.2878(8) 0.3203(5) 0.090(3) Uani 0.50 1 d PD D 2 H1B1 H 0.584(3) 0.294(8) 0.309(6) 0.108 Uiso 0.50 1 d PD E 2 H1B2 H 0.687(8) 0.208(3) 0.316(6) 0.108 Uiso 0.50 1 d PD F 2 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 N1 0.016(2) 0.017(2) 0.040(3) 0.002(2) -0.001(2) 0.0010(17) N2 0.021(2) 0.018(2) 0.041(2) 0.002(2) -0.005(2) 0.0046(17) N3 0.0156(18) 0.0156(18) 0.034(3) 0.002(2) -0.002(2) 0.003(3) N4 0.023(2) 0.014(2) 0.035(2) 0.005(2) -0.001(2) -0.0019(18) N5 0.018(2) 0.018(2) 0.046(4) 0.001(2) -0.001(2) -0.001(3) N6 0.017(2) 0.019(2) 0.043(3) -0.002(2) -0.003(2) 0.0014(18) C1 0.016(2) 0.024(3) 0.031(3) -0.002(3) -0.001(3) 0.002(2) C2 0.026(3) 0.024(3) 0.031(3) 0.000(3) 0.002(3) 0.000(2) C3 0.023(2) 0.023(2) 0.027(4) 0.000(3) 0.000(3) -0.009(3) C4 0.024(2) 0.024(2) 0.027(4) -0.003(3) 0.003(3) 0.004(3) C5 0.035(3) 0.014(2) 0.040(3) 0.001(2) -0.001(3) -0.002(2) C6 0.042(3) 0.024(3) 0.051(3) -0.002(3) 0.009(3) 0.001(3) C7 0.017(3) 0.020(3) 0.042(3) 0.004(2) 0.008(3) -0.002(2) C8 0.031(3) 0.024(3) 0.038(3) 0.000(3) -0.002(3) 0.005(2) C9 0.026(3) 0.030(3) 0.044(3) 0.007(3) -0.003(3) -0.005(3) C10 0.026(3) 0.026(3) 0.059(4) 0.005(3) 0.004(3) 0.005(3) C11 0.026(3) 0.025(3) 0.044(4) -0.002(3) 0.001(3) 0.000(2) C12 0.033(3) 0.028(3) 0.026(3) 0.004(3) 0.002(3) 0.001(2) C13 0.021(3) 0.016(2) 0.042(3) 0.001(3) 0.000(3) 0.000(2) C14 0.031(3) 0.038(3) 0.042(3) 0.003(3) 0.000(3) -0.009(3) C15 0.043(4) 0.048(4) 0.042(4) -0.007(3) 0.002(3) -0.014(3) C16 0.029(3) 0.032(3) 0.065(4) -0.003(3) -0.004(3) -0.001(3) C17 0.037(3) 0.039(4) 0.048(4) 0.011(3) -0.004(3) -0.010(3) C18 0.035(3) 0.035(3) 0.043(3) -0.008(3) -0.006(3) -0.013(3) O1A 0.043(6) 0.059(6) 0.103(7) 0.005(5) 0.015(5) 0.006(4) O1B 0.075(8) 0.083(8) 0.112(8) -0.013(7) -0.012(7) -0.004(6) _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 N1 C1 1.330(5) . ? N1 C2 1.349(5) . ? N2 C3 1.330(4) . ? N2 C2 1.351(5) . ? N3 C1 1.396(5) 7_645 ? N3 C1 1.396(5) . ? N3 C3 1.410(7) . ? N4 C1 1.327(5) . ? N4 C4 1.366(4) . ? N5 C4 1.321(7) . ? N5 C5 1.466(5) . ? N5 C5 1.466(5) 7_645 ? N6 C2 1.355(5) . ? N6 C13 1.433(5) . ? N6 C7 1.465(5) . ? C3 N2 1.330(4) 7_645 ? C4 N4 1.366(4) 7_645 ? C5 C6 1.509(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.380(6) . ? C7 C12 1.386(6) . ? C8 C9 1.378(6) . ? C8 H8 0.9500 . ? C9 C10 1.383(6) . ? C9 H9 0.9500 . ? C10 C11 1.382(6) . ? C10 H10 0.9500 . ? C11 C12 1.395(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.371(6) . ? C13 C18 1.379(6) . ? C14 C15 1.412(7) . ? C14 H14 0.9500 . ? C15 C16 1.373(6) . ? C15 H15 0.9500 . ? C16 C17 1.388(7) . ? C16 H16 0.9500 . ? C17 C18 1.402(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O1A H1A1 1.046(18) . ? O1A H1A2 1.046(18) . ? O1B H1B1 1.046(18) . ? O1B H1B2 1.046(18) . ? 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 C1 N1 C2 116.1(4) . . ? C3 N2 C2 115.8(4) . . ? C1 N3 C1 119.4(5) 7_645 . ? C1 N3 C3 120.3(3) 7_645 . ? C1 N3 C3 120.3(3) . . ? C1 N4 C4 116.5(4) . . ? C4 N5 C5 121.6(3) . . ? C4 N5 C5 121.6(3) . 7_645 ? C5 N5 C5 116.8(5) . 7_645 ? C2 N6 C13 122.8(4) . . ? C2 N6 C7 120.9(4) . . ? C13 N6 C7 115.8(4) . . ? N4 C1 N1 119.5(4) . . ? N4 C1 N3 120.7(4) . . ? N1 C1 N3 119.8(4) . . ? N1 C2 N2 128.3(4) . . ? N1 C2 N6 115.4(4) . . ? N2 C2 N6 116.3(4) . . ? N2 C3 N2 120.6(5) 7_645 . ? N2 C3 N3 119.7(3) 7_645 . ? N2 C3 N3 119.7(3) . . ? N5 C4 N4 117.1(3) . 7_645 ? N5 C4 N4 117.1(3) . . ? N4 C4 N4 125.9(6) 7_645 . ? N5 C5 C6 111.3(3) . . ? N5 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N5 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 121.4(5) . . ? C8 C7 N6 120.2(4) . . ? C12 C7 N6 118.3(4) . . ? C9 C8 C7 118.8(5) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.8(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.5(5) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.3(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C7 C12 C11 119.3(5) . . ? C7 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C18 121.1(4) . . ? C14 C13 N6 120.5(5) . . ? C18 C13 N6 118.3(5) . . ? C13 C14 C15 119.6(5) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 119.7(5) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.3(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 120.0(5) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 119.3(5) . . ? C13 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? H1A1 O1A H1A2 108(3) . . ? H1B1 O1B H1B2 108(3) . . ? 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 C4 N4 C1 N1 174.4(3) . . . . ? C4 N4 C1 N3 -5.6(6) . . . . ? C2 N1 C1 N4 178.4(4) . . . . ? C2 N1 C1 N3 -1.6(7) . . . . ? C1 N3 C1 N4 3.0(3) 7_645 . . . ? C3 N3 C1 N4 -177.0(3) . . . . ? C1 N3 C1 N1 -177.0(5) 7_645 . . . ? C3 N3 C1 N1 3.0(5) . . . . ? C1 N1 C2 N2 -1.7(8) . . . . ? C1 N1 C2 N6 178.3(4) . . . . ? C3 N2 C2 N1 3.3(7) . . . . ? C3 N2 C2 N6 -176.7(3) . . . . ? C13 N6 C2 N1 -177.4(4) . . . . ? C7 N6 C2 N1 -6.1(7) . . . . ? C13 N6 C2 N2 2.6(7) . . . . ? C7 N6 C2 N2 173.9(4) . . . . ? C2 N2 C3 N2 178.4(4) . . . 7_645 ? C2 N2 C3 N3 -1.6(4) . . . . ? C1 N3 C3 N2 -1.3(3) 7_645 . . 7_645 ? C1 N3 C3 N2 178.7(3) . . . 7_645 ? C1 N3 C3 N2 178.7(3) 7_645 . . . ? C1 N3 C3 N2 -1.3(3) . . . . ? C5 N5 C4 N4 0.2(3) . . . 7_645 ? C5 N5 C4 N4 -179.8(3) 7_645 . . 7_645 ? C5 N5 C4 N4 -179.8(3) . . . . ? C5 N5 C4 N4 0.2(3) 7_645 . . . ? C1 N4 C4 N5 -177.2(3) . . . . ? C1 N4 C4 N4 2.8(3) . . . 7_645 ? C4 N5 C5 C6 -93.6(4) . . . . ? C5 N5 C5 C6 86.4(4) 7_645 . . . ? C2 N6 C7 C8 -65.9(6) . . . . ? C13 N6 C7 C8 106.0(5) . . . . ? C2 N6 C7 C12 117.4(5) . . . . ? C13 N6 C7 C12 -70.8(6) . . . . ? C12 C7 C8 C9 -1.8(7) . . . . ? N6 C7 C8 C9 -178.4(4) . . . . ? C7 C8 C9 C10 1.0(7) . . . . ? C8 C9 C10 C11 0.0(7) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C8 C7 C12 C11 1.6(7) . . . . ? N6 C7 C12 C11 178.3(4) . . . . ? C10 C11 C12 C7 -0.6(6) . . . . ? C2 N6 C13 C14 -89.1(6) . . . . ? C7 N6 C13 C14 99.2(5) . . . . ? C2 N6 C13 C18 95.5(6) . . . . ? C7 N6 C13 C18 -76.2(6) . . . . ? C18 C13 C14 C15 0.1(7) . . . . ? N6 C13 C14 C15 -175.2(5) . . . . ? C13 C14 C15 C16 1.5(8) . . . . ? C14 C15 C16 C17 -1.9(8) . . . . ? C15 C16 C17 C18 0.7(8) . . . . ? C14 C13 C18 C17 -1.4(7) . . . . ? N6 C13 C18 C17 174.1(4) . . . . ? C16 C17 C18 C13 0.9(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A1 O1B 1.046(18) 1.92(4) 2.903(13) 156(7) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.279 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.085