# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/256 data_global #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_author ; E. F. Paulus Hoechst Marion Roussel Deutschland GmbH, G864 D-65926 Frankfurt/Main, Germany present address: Institut fuer Mineralogie/Kristallographie der Johann Wolfgang Goethe-Universitaet Senckenberganlage 30, 60325 Frankfurt/Main, Germany ; _publ_contact_author_email e.paulus@kristall.uni-frankfurt.de #------------------------------------------------------------------------- # Publication details loop_ _publ_author_name ; Ch. Schmidt Johannes Gutenberg-Universitaet, Fachbereich Chemie und Pharmazie, Abt. Lehramt Chemie, Duesbergweg 10-14, D-55099 Mainz, Germany ; ; E. F. Paulus Hoechst Marion Roussel Deutschland GmbH, G864 D-65926 Frankfurt/Main, Germany present address: Institut fuer Mineralogie/Kristallographie der Johann Wolfgang Goethe-Universitaet Senckenberganlage 30, 60325 Frankfurt/Main, Germany ; ; V. Boehmer Johannes Gutenberg-Universitaet, Fachbereich Chemie und Pharmazie, Abt. Lehramt Chemie, Duesbergweg 10-14, D-55099 Mainz, Germany ; ; W. Vogt Johannes Gutenberg-Universitaet, Fachbereich Chemie und Pharmazie, Abt. Lehramt Chemie, Duesbergweg 10-14, D-55099 Mainz, Germany ; _journal_name_full 'New J. Chem.' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag include any ASCII file output by a chemical drawing # package # Against _type record, for example, ChemDraw # Against _records supply the chemical connectivity records _chemical_name_systematic ; 1,3,5-Tris[(R)-1-indyl]-hexahydro-1,3,5-triazin ; _chemical_name_common '?' _chemical_formula_moiety 'C30H32N3' _chemical_formula_sum 'C30H32N3' _chemical_formula_weight '1738.34' _chemical_melting_point ? _ccdc_compound_id '?' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_chemdiag_type '' _loop ; ; _exptl_crystal_density_diffrn '1.178' _exptl_crystal_colour '?' _diffrn_radiation_type 'Mo-K-alpha' _diffrn_measurement_device ; Bruker AXS four-circle-diffractometer with CCD and rotating anode ; _ccdc_temp_data_collection '293(2)' _ccdc_ls_R_squared '0.0848' _refine_ls_abs_structure_details 'abs.struct. by chem. synthesis' _ccdc_disorder 'no disorder' _ccdc_comments '' #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # Do not include structure factors data_sh625 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5-Tris[(R)-1-indyl]-hexahydro-1,3,5-triazin ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 N3' _chemical_formula_weight 1738.34 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 ? _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.191(1) _cell_length_b 12.292(1) _cell_length_c 21.682(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2449.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 'all' _cell_measurement_theta_min '1.9' _cell_measurement_theta_max '26.4' _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type 'experimental' _exptl_absorpt_correction_T_min '0.50774' _exptl_absorpt_correction_T_max '0.8620' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode, focus: 0.5 x 5mm' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'AXS four-circle-diffractometer with CCD' _diffrn_measurement_method 'phi- and chi-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13061 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.36 _reflns_number_total 4274 _reflns_number_gt 3429 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'mostly difmap; less part geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack '-1(2) (formally); impssible by X-ray' _refine_ls_number_reflns 4274 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _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 C01 C 0.04050(19) 0.75181(13) 0.30038(7) 0.0458(4) Uani 1 1 d . . . C02 C -0.10301(19) 0.91221(12) 0.31286(7) 0.0436(3) Uani 1 1 d . . . C03 C 0.00056(19) 0.87520(13) 0.21615(7) 0.0452(4) Uani 1 1 d . . . C04 C 0.12374(18) 0.70033(12) 0.19798(7) 0.0449(4) Uani 1 1 d . . . C05 C 0.28033(19) 0.74295(16) 0.19001(9) 0.0581(4) Uani 1 1 d . . . C06 C 0.3338(2) 0.69050(19) 0.12967(10) 0.0659(5) Uani 1 1 d . . . C07 C 0.1961(2) 0.67408(13) 0.09349(8) 0.0538(4) Uani 1 1 d . . . C08 C 0.1763(3) 0.65254(16) 0.03090(9) 0.0692(6) Uani 1 1 d . . . C09 C 0.0382(3) 0.63869(16) 0.00848(9) 0.0734(6) Uani 1 1 d . . . C10 C -0.0804(3) 0.64870(16) 0.04630(9) 0.0680(5) Uani 1 1 d . . . C11 C -0.0618(2) 0.67033(14) 0.10868(8) 0.0542(4) Uani 1 1 d . . . C12 C 0.07675(19) 0.68243(11) 0.13175(7) 0.0454(4) Uani 1 1 d . . . C13 C -0.0803(2) 0.78818(12) 0.39947(7) 0.0474(4) Uani 1 1 d . . . C14 C 0.0504(3) 0.83695(17) 0.43459(9) 0.0692(6) Uani 1 1 d . . . C15 C 0.0980(4) 0.7564(3) 0.48038(18) 0.1583(17) Uani 1 1 d . . . H15A H 0.0749 0.7809 0.5218 0.237 Uiso 1 1 calc R . . H15B H 0.2022 0.7448 0.4775 0.237 Uiso 1 1 calc R . . C16 C 0.0173(2) 0.65339(16) 0.46571(10) 0.0753(6) Uani 1 1 d . . . C17 C 0.0314(3) 0.5509(2) 0.49198(15) 0.1064(10) Uani 1 1 d . . . C18 C -0.0541(3) 0.46832(18) 0.47278(12) 0.0827(7) Uani 1 1 d . . . C19 C -0.1568(3) 0.48594(16) 0.42840(10) 0.0717(6) Uani 1 1 d . . . C20 C -0.1699(3) 0.58792(16) 0.40151(8) 0.0678(5) Uani 1 1 d . . . C21 C -0.08269(18) 0.67114(12) 0.42049(6) 0.0444(4) Uani 1 1 d . . . C22 C -0.26388(19) 0.87490(15) 0.22301(8) 0.0521(4) Uani 1 1 d . . . C23 C -0.3003(3) 0.9247(2) 0.15949(9) 0.0763(6) Uani 1 1 d . . . C24 C -0.3961(3) 1.0230(2) 0.17305(12) 0.0842(7) Uani 1 1 d . . . C25 C -0.4677(2) 0.99323(16) 0.23295(10) 0.0686(5) Uani 1 1 d . . . C26 C -0.5930(3) 1.0349(2) 0.26177(17) 0.0925(8) Uani 1 1 d . . . C27 C -0.6395(3) 0.9880(3) 0.31642(18) 0.0984(9) Uani 1 1 d . . . C28 C -0.5673(3) 0.9037(3) 0.34296(14) 0.0918(7) Uani 1 1 d . . . C29 C -0.4442(2) 0.86273(19) 0.31540(10) 0.0726(6) Uani 1 1 d . . . C30 C -0.39413(18) 0.90803(14) 0.26050(8) 0.0555(4) Uani 1 1 d . . . H011 H 0.0468(16) 0.6722(13) 0.3094(7) 0.041(4) Uiso 1 1 d . . . H012 H 0.1376(19) 0.7907(13) 0.3131(7) 0.050(4) Uiso 1 1 d . . . H021 H -0.1865(18) 0.9420(12) 0.3351(7) 0.045(4) Uiso 1 1 d . . . H022 H -0.0138(16) 0.9590(11) 0.3235(6) 0.035(4) Uiso 1 1 d . . . H031 H 0.0856(19) 0.9210(13) 0.2288(7) 0.044(4) Uiso 1 1 d . . . H032 H -0.0183(17) 0.8755(12) 0.1717(8) 0.044(4) Uiso 1 1 d . . . H04 H 0.1257(19) 0.6313(15) 0.2163(7) 0.053(4) Uiso 1 1 d . . . H051 H 0.2839(18) 0.8238(15) 0.1858(7) 0.053(5) Uiso 1 1 d . . . H052 H 0.348(2) 0.7213(16) 0.2264(9) 0.072(5) Uiso 1 1 d . . . H061 H 0.382(3) 0.6212(19) 0.1404(10) 0.084(6) Uiso 1 1 d . . . H062 H 0.405(2) 0.7404(18) 0.1096(9) 0.076(6) Uiso 1 1 d . . . H08 H 0.261(2) 0.6436(17) 0.0037(10) 0.079(6) Uiso 1 1 d . . . H09 H 0.026(2) 0.6208(17) -0.0373(10) 0.088(6) Uiso 1 1 d . . . H10 H -0.179(3) 0.6352(18) 0.0349(10) 0.084(7) Uiso 1 1 d . . . H11 H -0.144(2) 0.6739(14) 0.1361(8) 0.052(5) Uiso 1 1 d . . . H13 H -0.1729(19) 0.8199(13) 0.4136(8) 0.051(4) Uiso 1 1 d . . . H141 H 0.043(3) 0.909(3) 0.4492(12) 0.122(9) Uiso 1 1 d . . . H142 H 0.123(4) 0.868(3) 0.4097(15) 0.134(11) Uiso 1 1 d . . . H17 H 0.089(4) 0.546(3) 0.5230(15) 0.135(11) Uiso 1 1 d . . . H18 H -0.051(3) 0.398(2) 0.4926(11) 0.106(8) Uiso 1 1 d . . . H19 H -0.227(3) 0.428(2) 0.4199(11) 0.100(8) Uiso 1 1 d . . . H20 H -0.245(3) 0.603(2) 0.3675(12) 0.110(8) Uiso 1 1 d . . . H22 H -0.2550(17) 0.7981(15) 0.2205(7) 0.048(4) Uiso 1 1 d . . . H231 H -0.358(3) 0.8717(19) 0.1363(11) 0.095(7) Uiso 1 1 d . . . H232 H -0.204(3) 0.9444(18) 0.1339(11) 0.092(7) Uiso 1 1 d . . . H241 H -0.477(3) 1.042(2) 0.1381(12) 0.119(9) Uiso 1 1 d . . . H242 H -0.335(3) 1.090(2) 0.1813(13) 0.121(10) Uiso 1 1 d . . . H26 H -0.641(3) 1.091(2) 0.2385(11) 0.103(8) Uiso 1 1 d . . . H27 H -0.732(3) 1.021(2) 0.3355(13) 0.111(8) Uiso 1 1 d . . . H28 H -0.597(4) 0.868(3) 0.3871(16) 0.152(12) Uiso 1 1 d . . . H29 H -0.381(3) 0.802(2) 0.3332(11) 0.105(8) Uiso 1 1 d . . . N1 N 0.01758(14) 0.76085(9) 0.23398(5) 0.0424(3) Uani 1 1 d . . . N2 N -0.08520(14) 0.79864(9) 0.33179(5) 0.0424(3) Uani 1 1 d . . . N3 N -0.12620(14) 0.92268(9) 0.24661(5) 0.0437(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C01 0.0508(9) 0.0430(8) 0.0435(8) 0.0041(6) -0.0007(8) 0.0031(8) C02 0.0483(8) 0.0398(7) 0.0428(8) -0.0023(6) -0.0008(8) 0.0036(8) C03 0.0506(9) 0.0421(8) 0.0428(8) 0.0037(6) 0.0024(8) 0.0020(8) C04 0.0488(9) 0.0373(7) 0.0486(8) 0.0036(6) 0.0019(8) 0.0040(7) C05 0.0483(9) 0.0586(11) 0.0673(11) -0.0002(9) 0.0035(9) 0.0034(9) C06 0.0522(10) 0.0721(13) 0.0733(12) 0.0063(10) 0.0132(10) 0.0115(11) C07 0.0599(10) 0.0467(9) 0.0549(10) 0.0022(7) 0.0152(9) 0.0090(8) C08 0.0920(16) 0.0631(11) 0.0523(10) -0.0002(8) 0.0202(12) 0.0156(12) C09 0.1028(17) 0.0687(12) 0.0487(10) -0.0039(9) 0.0002(12) 0.0124(12) C10 0.0816(14) 0.0608(11) 0.0615(11) -0.0079(8) -0.0154(12) 0.0026(11) C11 0.0598(11) 0.0479(8) 0.0548(9) -0.0046(7) 0.0027(9) -0.0028(9) C12 0.0555(9) 0.0345(7) 0.0462(8) 0.0009(6) 0.0062(8) 0.0006(8) C13 0.0568(9) 0.0476(8) 0.0379(8) -0.0009(6) 0.0005(8) 0.0007(9) C14 0.0932(16) 0.0609(11) 0.0536(10) -0.0009(8) -0.0152(11) -0.0208(12) C15 0.184(3) 0.0929(18) 0.198(3) 0.049(2) -0.133(3) -0.055(2) C16 0.0751(13) 0.0653(12) 0.0856(13) 0.0165(10) -0.0271(12) -0.0048(11) C17 0.111(2) 0.0825(17) 0.126(2) 0.0377(15) -0.049(2) -0.0009(16) C18 0.0985(17) 0.0581(12) 0.0916(16) 0.0198(11) 0.0187(15) 0.0087(13) C19 0.0905(15) 0.0561(11) 0.0684(12) -0.0008(9) 0.0198(13) -0.0158(12) C20 0.0820(13) 0.0648(11) 0.0566(10) 0.0051(9) -0.0077(11) -0.0148(12) C21 0.0475(8) 0.0496(8) 0.0360(7) -0.0017(6) 0.0085(7) 0.0004(8) C22 0.0535(9) 0.0502(10) 0.0527(10) -0.0074(8) -0.0081(8) 0.0030(9) C23 0.0722(13) 0.1024(17) 0.0543(11) -0.0049(12) -0.0177(11) 0.0115(14) C24 0.0794(14) 0.0895(16) 0.0836(15) 0.0104(12) -0.0287(14) 0.0175(14) C25 0.0512(10) 0.0688(11) 0.0858(14) -0.0196(10) -0.0212(11) 0.0067(10) C26 0.0564(12) 0.0795(15) 0.142(2) -0.0335(16) -0.0269(17) 0.0143(13) C27 0.0507(12) 0.116(2) 0.128(2) -0.052(2) 0.0118(16) -0.0093(15) C28 0.0572(12) 0.1107(19) 0.1075(19) -0.0271(16) 0.0112(14) -0.0144(15) C29 0.0525(10) 0.0817(13) 0.0837(14) -0.0112(11) 0.0063(11) -0.0138(11) C30 0.0430(8) 0.0599(9) 0.0636(10) -0.0143(8) -0.0052(9) 0.0014(9) N1 0.0487(7) 0.0388(6) 0.0397(6) 0.0034(5) 0.0047(6) 0.0040(6) N2 0.0491(7) 0.0410(6) 0.0370(6) 0.0001(5) 0.0000(6) 0.0032(6) N3 0.0491(7) 0.0414(6) 0.0406(6) 0.0013(5) -0.0008(6) 0.0043(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 C01 N1 1.4590(19) . ? C01 N2 1.460(2) . ? C01 H011 1.000(16) . ? C01 H012 1.049(18) . ? C02 N3 1.4578(19) . ? C02 N2 1.4642(19) . ? C02 H021 0.978(17) . ? C02 H022 1.028(15) . ? C03 N3 1.461(2) . ? C03 N1 1.4661(19) . ? C03 H031 1.001(17) . ? C03 H032 0.979(16) . ? C04 N1 1.454(2) . ? C04 C12 1.516(2) . ? C04 C05 1.541(2) . ? C04 H04 0.937(18) . ? C05 C06 1.539(3) . ? C05 H051 0.999(18) . ? C05 H052 1.04(2) . ? C06 C07 1.503(3) . ? C06 H061 0.99(2) . ? C06 H062 1.00(2) . ? C07 C12 1.379(2) . ? C07 C08 1.395(3) . ? C08 C09 1.369(3) . ? C08 H08 0.98(2) . ? C09 C10 1.370(3) . ? C09 H09 1.02(2) . ? C10 C11 1.389(3) . ? C10 H10 0.95(2) . ? C11 C12 1.376(3) . ? C11 H11 0.965(18) . ? C13 N2 1.4737(18) . ? C13 C21 1.509(2) . ? C13 C14 1.543(3) . ? C13 H13 0.985(18) . ? C14 C15 1.469(3) . ? C14 H141 0.94(3) . ? C14 H142 0.94(3) . ? C15 C16 1.501(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.362(3) . ? C16 C17 1.388(3) . ? C17 C18 1.350(4) . ? C17 H17 0.86(3) . ? C18 C19 1.365(3) . ? C18 H18 0.97(3) . ? C19 C20 1.388(3) . ? C19 H19 0.98(3) . ? C20 C21 1.363(3) . ? C20 H20 1.02(3) . ? C22 N3 1.486(2) . ? C22 C30 1.503(3) . ? C22 C23 1.544(3) . ? C22 H22 0.950(18) . ? C23 C24 1.524(3) . ? C23 H231 0.98(3) . ? C23 H232 1.07(2) . ? C24 C25 1.501(3) . ? C24 H241 1.09(3) . ? C24 H242 1.01(3) . ? C25 C30 1.382(3) . ? C25 C26 1.407(3) . ? C26 C27 1.385(4) . ? C26 H26 0.96(3) . ? C27 C28 1.359(4) . ? C27 H27 1.03(3) . ? C28 C29 1.375(3) . ? C28 H28 1.09(4) . ? C29 C30 1.393(3) . ? C29 H29 1.02(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C01 N2 108.43(12) . . ? N1 C01 H011 106.0(8) . . ? N2 C01 H011 109.9(9) . . ? N1 C01 H012 110.3(9) . . ? N2 C01 H012 111.8(9) . . ? H011 C01 H012 110.2(13) . . ? N3 C02 N2 112.14(11) . . ? N3 C02 H021 109.7(9) . . ? N2 C02 H021 107.9(9) . . ? N3 C02 H022 106.8(8) . . ? N2 C02 H022 112.4(8) . . ? H021 C02 H022 107.8(11) . . ? N3 C03 N1 110.42(13) . . ? N3 C03 H031 105.9(8) . . ? N1 C03 H031 112.5(9) . . ? N3 C03 H032 107.6(9) . . ? N1 C03 H032 106.4(8) . . ? H031 C03 H032 114.0(13) . . ? N1 C04 C12 113.06(13) . . ? N1 C04 C05 120.85(13) . . ? C12 C04 C05 102.07(13) . . ? N1 C04 H04 104.4(10) . . ? C12 C04 H04 106.0(10) . . ? C05 C04 H04 109.7(11) . . ? C06 C05 C04 104.56(15) . . ? C06 C05 H051 109.1(9) . . ? C04 C05 H051 112.3(10) . . ? C06 C05 H052 110.2(11) . . ? C04 C05 H052 112.8(11) . . ? H051 C05 H052 107.8(14) . . ? C07 C06 C05 103.35(15) . . ? C07 C06 H061 112.6(13) . . ? C05 C06 H061 107.8(12) . . ? C07 C06 H062 114.0(11) . . ? C05 C06 H062 108.9(12) . . ? H061 C06 H062 109.8(18) . . ? C12 C07 C08 119.67(19) . . ? C12 C07 C06 110.25(15) . . ? C08 C07 C06 130.08(19) . . ? C09 C08 C07 119.4(2) . . ? C09 C08 H08 120.6(12) . . ? C07 C08 H08 120.0(12) . . ? C08 C09 C10 120.92(19) . . ? C08 C09 H09 118.3(13) . . ? C10 C09 H09 120.8(13) . . ? C09 C10 C11 120.1(2) . . ? C09 C10 H10 125.7(14) . . ? C11 C10 H10 113.8(14) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 120.0(10) . . ? C10 C11 H11 120.7(10) . . ? C11 C12 C07 120.63(15) . . ? C11 C12 C04 128.58(16) . . ? C07 C12 C04 110.73(15) . . ? N2 C13 C21 112.54(12) . . ? N2 C13 C14 118.77(15) . . ? C21 C13 C14 103.45(14) . . ? N2 C13 H13 104.4(10) . . ? C21 C13 H13 105.8(10) . . ? C14 C13 H13 111.4(10) . . ? C15 C14 C13 107.67(18) . . ? C15 C14 H141 115.3(17) . . ? C13 C14 H141 118.2(18) . . ? C15 C14 H142 116.8(19) . . ? C13 C14 H142 115.4(18) . . ? H141 C14 H142 82(2) . . ? C14 C15 C16 106.14(19) . . ? C14 C15 H15A 110.5 . . ? C16 C15 H15A 110.5 . . ? C14 C15 H15B 110.5 . . ? C16 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? C21 C16 C17 120.3(2) . . ? C21 C16 C15 110.55(17) . . ? C17 C16 C15 129.2(2) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 124(2) . . ? C16 C17 H17 116(2) . . ? C17 C18 C19 120.0(2) . . ? C17 C18 H18 121.3(15) . . ? C19 C18 H18 118.4(15) . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 118.5(15) . . ? C20 C19 H19 121.1(15) . . ? C21 C20 C19 120.0(2) . . ? C21 C20 H20 118.3(15) . . ? C19 C20 H20 121.7(15) . . ? C16 C21 C20 119.62(16) . . ? C16 C21 C13 111.12(15) . . ? C20 C21 C13 129.24(16) . . ? N3 C22 C30 112.65(13) . . ? N3 C22 C23 109.59(17) . . ? C30 C22 C23 101.67(15) . . ? N3 C22 H22 109.8(10) . . ? C30 C22 H22 111.6(10) . . ? C23 C22 H22 111.2(10) . . ? C24 C23 C22 105.51(17) . . ? C24 C23 H231 108.4(14) . . ? C22 C23 H231 108.2(14) . . ? C24 C23 H232 113.4(13) . . ? C22 C23 H232 111.9(13) . . ? H231 C23 H232 109.2(19) . . ? C25 C24 C23 103.13(18) . . ? C25 C24 H241 110.7(14) . . ? C23 C24 H241 115.5(14) . . ? C25 C24 H242 106.7(16) . . ? C23 C24 H242 111.1(16) . . ? H241 C24 H242 109(2) . . ? C30 C25 C26 119.0(2) . . ? C30 C25 C24 110.11(17) . . ? C26 C25 C24 130.9(2) . . ? C27 C26 C25 118.7(3) . . ? C27 C26 H26 127.4(16) . . ? C25 C26 H26 113.7(16) . . ? C28 C27 C26 121.9(2) . . ? C28 C27 H27 122.2(16) . . ? C26 C27 H27 115.9(16) . . ? C27 C28 C29 119.8(3) . . ? C27 C28 H28 123.8(19) . . ? C29 C28 H28 116.3(19) . . ? C28 C29 C30 119.8(3) . . ? C28 C29 H29 124.8(15) . . ? C30 C29 H29 115.3(14) . . ? C25 C30 C29 120.71(18) . . ? C25 C30 C22 111.18(17) . . ? C29 C30 C22 128.11(17) . . ? C04 N1 C01 113.19(12) . . ? C04 N1 C03 114.86(12) . . ? C01 N1 C03 110.41(12) . . ? C01 N2 C02 109.49(12) . . ? C01 N2 C13 113.96(12) . . ? C02 N2 C13 111.46(11) . . ? C02 N3 C03 107.07(12) . . ? C02 N3 C22 115.39(13) . . ? C03 N3 C22 111.45(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C04 C05 C06 -155.48(15) . . . . ? C12 C04 C05 C06 -29.02(18) . . . . ? C04 C05 C06 C07 28.0(2) . . . . ? C05 C06 C07 C12 -16.2(2) . . . . ? C05 C06 C07 C08 164.12(18) . . . . ? C12 C07 C08 C09 -0.8(3) . . . . ? C06 C07 C08 C09 178.8(2) . . . . ? C07 C08 C09 C10 1.8(3) . . . . ? C08 C09 C10 C11 -1.7(3) . . . . ? C09 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C07 0.5(2) . . . . ? C10 C11 C12 C04 -176.54(15) . . . . ? C08 C07 C12 C11 -0.4(2) . . . . ? C06 C07 C12 C11 179.94(16) . . . . ? C08 C07 C12 C04 177.15(15) . . . . ? C06 C07 C12 C04 -2.53(19) . . . . ? N1 C04 C12 C11 -31.3(2) . . . . ? C05 C04 C12 C11 -162.64(16) . . . . ? N1 C04 C12 C07 151.46(13) . . . . ? C05 C04 C12 C07 20.08(17) . . . . ? N2 C13 C14 C15 -135.4(3) . . . . ? C21 C13 C14 C15 -9.9(3) . . . . ? C13 C14 C15 C16 10.1(4) . . . . ? C14 C15 C16 C21 -6.6(4) . . . . ? C14 C15 C16 C17 174.4(3) . . . . ? C21 C16 C17 C18 0.0(4) . . . . ? C15 C16 C17 C18 178.9(3) . . . . ? C16 C17 C18 C19 -1.4(4) . . . . ? C17 C18 C19 C20 2.2(4) . . . . ? C18 C19 C20 C21 -1.6(3) . . . . ? C17 C16 C21 C20 0.6(3) . . . . ? C15 C16 C21 C20 -178.5(3) . . . . ? C17 C16 C21 C13 179.2(2) . . . . ? C15 C16 C21 C13 0.2(3) . . . . ? C19 C20 C21 C16 0.2(3) . . . . ? C19 C20 C21 C13 -178.14(18) . . . . ? N2 C13 C21 C16 135.41(16) . . . . ? C14 C13 C21 C16 6.0(2) . . . . ? N2 C13 C21 C20 -46.1(2) . . . . ? C14 C13 C21 C20 -175.56(19) . . . . ? N3 C22 C23 C24 -91.4(2) . . . . ? C30 C22 C23 C24 28.0(2) . . . . ? C22 C23 C24 C25 -27.3(3) . . . . ? C23 C24 C25 C30 16.2(2) . . . . ? C23 C24 C25 C26 -161.6(2) . . . . ? C30 C25 C26 C27 -0.9(3) . . . . ? C24 C25 C26 C27 176.8(2) . . . . ? C25 C26 C27 C28 0.3(4) . . . . ? C26 C27 C28 C29 0.1(4) . . . . ? C27 C28 C29 C30 0.1(3) . . . . ? C26 C25 C30 C29 1.0(3) . . . . ? C24 C25 C30 C29 -177.09(18) . . . . ? C26 C25 C30 C22 179.97(17) . . . . ? C24 C25 C30 C22 1.9(2) . . . . ? C28 C29 C30 C25 -0.6(3) . . . . ? C28 C29 C30 C22 -179.38(18) . . . . ? N3 C22 C30 C25 98.47(17) . . . . ? C23 C22 C30 C25 -18.7(2) . . . . ? N3 C22 C30 C29 -82.7(2) . . . . ? C23 C22 C30 C29 160.11(19) . . . . ? C12 C04 N1 C01 163.43(13) . . . . ? C05 C04 N1 C01 -75.30(18) . . . . ? C12 C04 N1 C03 -68.51(16) . . . . ? C05 C04 N1 C03 52.8(2) . . . . ? N2 C01 N1 C04 -170.04(12) . . . . ? N2 C01 N1 C03 59.62(17) . . . . ? N3 C03 N1 C04 169.27(12) . . . . ? N3 C03 N1 C01 -61.28(17) . . . . ? N1 C01 N2 C02 -58.23(16) . . . . ? N1 C01 N2 C13 176.18(12) . . . . ? N3 C02 N2 C01 60.12(17) . . . . ? N3 C02 N2 C13 -172.87(14) . . . . ? C21 C13 N2 C01 -63.31(19) . . . . ? C14 C13 N2 C01 57.71(19) . . . . ? C21 C13 N2 C02 172.16(14) . . . . ? C14 C13 N2 C02 -66.8(2) . . . . ? N2 C02 N3 C03 -59.16(17) . . . . ? N2 C02 N3 C22 65.53(17) . . . . ? N1 C03 N3 C02 58.91(16) . . . . ? N1 C03 N3 C22 -68.14(16) . . . . ? C30 C22 N3 C02 48.04(19) . . . . ? C23 C22 N3 C02 160.44(14) . . . . ? C30 C22 N3 C03 170.42(14) . . . . ? C23 C22 N3 C03 -77.17(17) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.164 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.025