# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name Y.Shafran Y.Rozin T.Beryozkina S.Zhidovinov O.Eltsov J.Subbotina J.Leban R.Novikova V.Bakulev _publ_contact_author_name 'Julia Subbotina' _publ_contact_author_email v.a.bakulev@ustu.ru data_dc _database_code_depnum_ccdc_archive 'CCDC 867109' #TrackingRef '- TB-134.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N7 O4' _chemical_formula_sum 'C26 H25 N7 O4' _chemical_formula_weight 499.53 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8237(7) _cell_length_b 12.5753(9) _cell_length_c 24.9768(16) _cell_angle_alpha 83.919(6) _cell_angle_beta 83.430(6) _cell_angle_gamma 69.943(7) _cell_volume 2579.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4680 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 26.37 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.090 _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 295(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 'Xcalibur S CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21816 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0865 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 26.37 _reflns_number_total 10279 _reflns_number_gt 4680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0239P)^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 10279 _refine_ls_number_parameters 691 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 N12 N 0.10482(19) 0.94046(13) 0.40140(6) 0.0431(4) Uani 1 1 d . . . O4 O -0.32874(19) 0.64218(13) 0.36839(6) 0.0703(5) Uani 1 1 d . . . O6 O 0.07365(18) 0.67839(13) 0.14294(5) 0.0677(4) Uani 1 1 d . . . N1 N -0.43580(18) 0.93793(13) 0.09342(6) 0.0398(4) Uani 1 1 d . . . O2 O -0.57826(17) 0.66498(12) 0.07499(5) 0.0594(4) Uani 1 1 d . . . C8 C -0.5047(2) 0.85531(15) 0.10108(7) 0.0362(5) Uani 1 1 d . . . N5 N -0.1633(2) 0.50316(14) 0.20965(6) 0.0469(4) Uani 1 1 d . . . C11 C -0.6032(2) 0.84018(15) 0.15083(7) 0.0339(5) Uani 1 1 d . . . O5 O -0.04184(19) 0.79477(14) 0.20798(6) 0.0703(5) Uani 1 1 d . . . N8 N 0.3135(2) 0.52151(14) 0.28960(6) 0.0478(4) Uani 1 1 d . . . N3 N -0.3562(2) 0.84779(14) 0.02135(6) 0.0505(5) Uani 1 1 d . . . N4 N -0.8638(2) 0.98826(15) 0.13336(7) 0.0543(5) Uani 1 1 d . . . N6 N -0.0795(2) 0.44628(15) 0.25258(7) 0.0575(5) Uani 1 1 d . . . N2 N -0.3465(2) 0.93324(14) 0.04491(6) 0.0500(4) Uani 1 1 d . . . C43 C 0.0228(2) 0.86585(16) 0.40708(7) 0.0398(5) Uani 1 1 d . . . C12 C -0.7589(3) 0.90636(18) 0.16251(9) 0.0424(5) Uani 1 1 d . . . O8 O 0.09550(18) 0.67089(12) 0.52686(6) 0.0652(4) Uani 1 1 d . . . N7 N -0.1465(2) 0.50394(15) 0.29453(7) 0.0559(5) Uani 1 1 d . . . C7 C -0.4516(2) 0.79872(16) 0.05437(7) 0.0394(5) Uani 1 1 d . . . N13 N 0.1932(2) 0.92801(15) 0.44432(7) 0.0567(5) Uani 1 1 d . . . C15 C -0.5232(3) 0.75485(17) 0.19096(8) 0.0382(5) Uani 1 1 d . . . O1 O -0.4435(2) 0.66416(13) -0.00609(6) 0.0800(5) Uani 1 1 d . . . C17 C -0.2844(2) 0.59917(16) 0.22426(8) 0.0414(5) Uani 1 1 d . . . N10 N 0.2673(2) 0.52327(16) 0.20714(7) 0.0587(5) Uani 1 1 d . . . C16 C -0.3762(3) 0.67705(17) 0.18396(9) 0.0425(5) Uani 1 1 d . . . N9 N 0.3576(2) 0.46162(15) 0.24428(7) 0.0613(5) Uani 1 1 d . . . N14 N 0.1711(2) 0.84584(15) 0.47665(7) 0.0549(5) Uani 1 1 d . . . C38 C -0.0153(3) 0.77767(18) 0.32667(8) 0.0432(5) Uani 1 1 d . . . C18 C -0.2722(2) 0.59642(17) 0.27943(8) 0.0433(5) Uani 1 1 d . . . C35 C 0.0547(3) 0.7072(2) 0.19352(8) 0.0488(6) Uani 1 1 d . . . C9 C -0.4875(3) 0.70253(17) 0.03718(9) 0.0468(5) Uani 1 1 d . . . C6 C -0.4468(2) 1.02403(17) 0.12875(8) 0.0404(5) Uani 1 1 d . . . C33 C 0.1652(2) 0.62140(17) 0.22752(8) 0.0441(5) Uani 1 1 d . . . C40 C -0.2411(3) 0.92554(18) 0.36393(8) 0.0472(6) Uani 1 1 d . . . C39 C -0.0832(2) 0.85992(16) 0.36635(7) 0.0407(5) Uani 1 1 d . . . O7 O -0.0818(2) 0.68132(15) 0.46887(6) 0.1006(7) Uani 1 1 d . . . N11 N -0.3436(2) 1.00383(15) 0.39511(7) 0.0568(5) Uani 1 1 d . . . C47 C 0.1137(2) 1.02393(18) 0.35891(8) 0.0435(5) Uani 1 1 d . . . C34 C 0.1946(2) 0.62241(17) 0.28103(8) 0.0415(5) Uani 1 1 d . . . C37 C 0.1345(3) 0.70495(18) 0.32136(8) 0.0450(5) Uani 1 1 d . . . C32 C 0.3895(3) 0.46899(17) 0.33781(9) 0.0480(5) Uani 1 1 d . . . C1 C -0.3970(2) 0.99324(17) 0.17989(8) 0.0488(5) Uani 1 1 d . . . H1A H -0.3569 0.9171 0.1921 0.059 Uiso 1 1 calc R . . C44 C 0.0682(2) 0.80571(16) 0.45512(7) 0.0436(5) Uani 1 1 d . . . C52 C 0.1888(3) 0.99123(19) 0.30936(9) 0.0565(6) Uani 1 1 d . . . H52A H 0.2271 0.9150 0.3023 0.068 Uiso 1 1 calc R . . C51 C 0.2070(3) 1.0724(2) 0.27003(9) 0.0613(6) Uani 1 1 d . . . H51A H 0.2583 1.0507 0.2363 0.074 Uiso 1 1 calc R . . C45 C 0.0177(3) 0.71390(18) 0.48325(8) 0.0556(6) Uani 1 1 d . . . C21 C -0.1235(3) 0.45264(16) 0.15875(8) 0.0488(5) Uani 1 1 d . . . C19 C -0.3723(3) 0.6745(2) 0.31924(8) 0.0537(6) Uani 1 1 d . . . C48 C 0.0589(3) 1.1356(2) 0.36990(9) 0.0629(6) Uani 1 1 d . . . H48A H 0.0094 1.1574 0.4038 0.076 Uiso 1 1 calc R . . C5 C -0.5045(3) 1.13523(19) 0.11017(9) 0.0626(6) Uani 1 1 d . . . H5A H -0.5368 1.1551 0.0753 0.075 Uiso 1 1 calc R . . C10 C -0.6190(3) 0.56820(18) 0.06375(8) 0.0671(7) Uani 1 1 d . . . H10A H -0.6849 0.5490 0.0939 0.101 Uiso 1 1 calc R . . H10B H -0.5216 0.5049 0.0578 0.101 Uiso 1 1 calc R . . H10C H -0.6777 0.5864 0.0320 0.101 Uiso 1 1 calc R . . C31 C 0.5493(3) 0.40187(19) 0.33425(9) 0.0626(6) Uani 1 1 d . . . H31A H 0.6083 0.3915 0.3008 0.075 Uiso 1 1 calc R . . O3 O -0.4806(2) 0.75842(17) 0.30923(6) 0.1158(8) Uani 1 1 d . . . C49 C 0.0781(3) 1.2153(2) 0.33006(10) 0.0784(7) Uani 1 1 d . . . H49A H 0.0414 1.2915 0.3372 0.094 Uiso 1 1 calc R . . C27 C 0.3029(3) 0.4838(2) 0.38720(10) 0.0714(7) Uani 1 1 d . . . H27A H 0.1942 0.5288 0.3897 0.086 Uiso 1 1 calc R . . C22 C 0.0289(3) 0.42827(19) 0.13446(9) 0.0655(7) Uani 1 1 d . . . H22A H 0.1068 0.4463 0.1502 0.079 Uiso 1 1 calc R . . C2 C -0.4072(3) 1.0767(2) 0.21284(9) 0.0619(6) Uani 1 1 d . . . H2A H -0.3736 1.0569 0.2476 0.074 Uiso 1 1 calc R . . C50 C 0.1505(3) 1.1839(2) 0.28011(9) 0.0673(7) Uani 1 1 d . . . H50A H 0.1611 1.2386 0.2532 0.081 Uiso 1 1 calc R . . C25 C -0.2008(4) 0.3737(2) 0.08850(11) 0.0905(9) Uani 1 1 d . . . H25A H -0.2778 0.3541 0.0731 0.109 Uiso 1 1 calc R . . C14 C -0.8337(3) 1.0187(2) 0.07657(9) 0.0774(7) Uani 1 1 d . . . H14A H -0.7301 0.9689 0.0632 0.116 Uiso 1 1 calc R . . H14B H -0.8345 1.0956 0.0721 0.116 Uiso 1 1 calc R . . H14C H -0.9167 1.0117 0.0569 0.116 Uiso 1 1 calc R . . C36 C -0.0239(3) 0.7593(2) 0.10466(8) 0.0784(8) Uani 1 1 d . . . H36A H 0.0005 0.7294 0.0697 0.118 Uiso 1 1 calc R . . H36B H -0.0008 0.8289 0.1028 0.118 Uiso 1 1 calc R . . H36C H -0.1363 0.7735 0.1159 0.118 Uiso 1 1 calc R . . C4 C -0.5143(3) 1.2178(2) 0.14395(11) 0.0766(7) Uani 1 1 d . . . H4A H -0.5538 1.2940 0.1318 0.092 Uiso 1 1 calc R . . C3 C -0.4665(3) 1.1886(2) 0.19494(11) 0.0699(7) Uani 1 1 d . . . H3A H -0.4742 1.2447 0.2176 0.084 Uiso 1 1 calc R . . C42 C -0.3031(3) 1.0293(2) 0.44550(8) 0.0796(8) Uani 1 1 d . . . H42A H -0.1929 0.9848 0.4512 0.119 Uiso 1 1 calc R . . H42B H -0.3736 1.0116 0.4746 0.119 Uiso 1 1 calc R . . H42C H -0.3161 1.1085 0.4442 0.119 Uiso 1 1 calc R . . C26 C -0.2409(3) 0.4258(2) 0.13678(10) 0.0738(7) Uani 1 1 d . . . H26A H -0.3447 0.4423 0.1540 0.089 Uiso 1 1 calc R . . C30 C 0.6219(3) 0.3499(2) 0.38048(12) 0.0791(8) Uani 1 1 d . . . H30A H 0.7303 0.3042 0.3781 0.095 Uiso 1 1 calc R . . C41 C -0.5074(3) 1.0654(2) 0.38096(10) 0.0813(8) Uani 1 1 d . . . H41A H -0.5223 1.0430 0.3469 0.122 Uiso 1 1 calc R . . H41B H -0.5252 1.1454 0.3782 0.122 Uiso 1 1 calc R . . H41C H -0.5831 1.0485 0.4084 0.122 Uiso 1 1 calc R . . C46 C 0.0524(3) 0.5827(2) 0.55913(9) 0.0860(8) Uani 1 1 d . . . H46A H 0.1168 0.5587 0.5895 0.129 Uiso 1 1 calc R . . H46B H 0.0718 0.5195 0.5378 0.129 Uiso 1 1 calc R . . H46C H -0.0601 0.6108 0.5717 0.129 Uiso 1 1 calc R . . C20 C -0.4280(3) 0.7073(2) 0.41154(8) 0.0805(8) Uani 1 1 d . . . H20A H -0.3843 0.6750 0.4454 0.121 Uiso 1 1 calc R . . H20B H -0.5363 0.7058 0.4124 0.121 Uiso 1 1 calc R . . H20C H -0.4294 0.7843 0.4056 0.121 Uiso 1 1 calc R . . C13 C -1.0182(3) 1.0567(2) 0.15904(10) 0.0850(8) Uani 1 1 d . . . H13A H -1.0275 1.0304 0.1964 0.127 Uiso 1 1 calc R . . H13B H -1.1050 1.0502 0.1412 0.127 Uiso 1 1 calc R . . H13C H -1.0239 1.1347 0.1565 0.127 Uiso 1 1 calc R . . C24 C -0.0479(4) 0.3511(2) 0.06346(10) 0.0884(9) Uani 1 1 d . . . H24A H -0.0226 0.3181 0.0306 0.106 Uiso 1 1 calc R . . C28 C 0.3779(4) 0.4314(2) 0.43311(10) 0.0902(8) Uani 1 1 d . . . H28A H 0.3197 0.4417 0.4667 0.108 Uiso 1 1 calc R . . C23 C 0.0680(3) 0.3765(2) 0.08614(10) 0.0829(8) Uani 1 1 d . . . H23A H 0.1723 0.3591 0.0693 0.099 Uiso 1 1 calc R . . C29 C 0.5367(4) 0.3647(2) 0.42947(12) 0.0867(8) Uani 1 1 d . . . H29A H 0.5865 0.3294 0.4606 0.104 Uiso 1 1 calc R . . H16 H -0.319(2) 0.6723(14) 0.1487(7) 0.043(5) Uiso 1 1 d . . . H38 H -0.088(2) 0.7769(14) 0.3008(7) 0.046(5) Uiso 1 1 d . . . H15 H -0.5820(19) 0.7572(13) 0.2253(6) 0.034(5) Uiso 1 1 d . . . H37 H 0.211(2) 0.6998(14) 0.3466(7) 0.047(5) Uiso 1 1 d . . . H40 H -0.294(2) 0.9141(14) 0.3337(7) 0.054(6) Uiso 1 1 d . . . H12 H -0.805(2) 0.8942(15) 0.1983(7) 0.053(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N12 0.0493(11) 0.0409(11) 0.0405(10) -0.0007(8) -0.0141(8) -0.0144(9) O4 0.0849(12) 0.0734(12) 0.0399(9) -0.0031(8) -0.0097(8) -0.0093(9) O6 0.0757(11) 0.0726(12) 0.0430(9) -0.0117(8) -0.0157(8) -0.0043(9) N1 0.0441(10) 0.0376(11) 0.0360(10) -0.0017(8) -0.0002(8) -0.0129(9) O2 0.0784(11) 0.0606(11) 0.0496(9) -0.0217(8) 0.0135(8) -0.0373(9) C8 0.0359(12) 0.0330(12) 0.0355(12) 0.0006(9) -0.0068(9) -0.0058(10) N5 0.0521(11) 0.0354(11) 0.0425(11) 0.0019(8) -0.0063(9) -0.0016(9) C11 0.0364(13) 0.0324(12) 0.0310(11) -0.0016(9) -0.0020(9) -0.0096(11) O5 0.0725(11) 0.0646(12) 0.0536(10) -0.0061(8) -0.0115(8) 0.0055(10) N8 0.0493(11) 0.0399(11) 0.0503(11) -0.0061(9) -0.0090(9) -0.0075(10) N3 0.0577(12) 0.0498(12) 0.0393(10) -0.0036(9) 0.0014(9) -0.0137(10) N4 0.0384(11) 0.0551(13) 0.0537(12) 0.0066(10) 0.0006(9) -0.0003(10) N6 0.0588(12) 0.0465(12) 0.0536(12) 0.0044(10) -0.0128(10) -0.0001(10) N2 0.0566(12) 0.0529(12) 0.0383(10) 0.0003(9) 0.0047(9) -0.0194(10) C43 0.0429(13) 0.0347(13) 0.0415(13) -0.0082(10) -0.0059(10) -0.0102(11) C12 0.0408(14) 0.0428(14) 0.0413(14) -0.0031(11) -0.0010(11) -0.0118(12) O8 0.0908(12) 0.0615(11) 0.0532(9) 0.0171(8) -0.0310(9) -0.0365(9) N7 0.0590(13) 0.0493(13) 0.0470(11) 0.0028(9) -0.0100(10) -0.0024(11) C7 0.0443(13) 0.0383(13) 0.0323(12) -0.0019(10) 0.0028(10) -0.0118(11) N13 0.0676(13) 0.0589(13) 0.0541(12) 0.0038(10) -0.0267(10) -0.0300(11) C15 0.0469(14) 0.0384(14) 0.0304(12) -0.0021(10) -0.0018(11) -0.0165(12) O1 0.1318(15) 0.0688(12) 0.0460(9) -0.0239(8) 0.0222(10) -0.0456(11) C17 0.0447(13) 0.0322(13) 0.0426(13) 0.0020(10) -0.0037(10) -0.0082(11) N10 0.0632(13) 0.0515(13) 0.0553(12) -0.0109(10) -0.0110(10) -0.0075(11) C16 0.0476(15) 0.0367(14) 0.0371(13) -0.0016(10) -0.0007(11) -0.0074(12) N9 0.0691(13) 0.0491(13) 0.0588(13) -0.0150(10) -0.0102(11) -0.0061(11) N14 0.0675(13) 0.0563(13) 0.0502(11) 0.0049(9) -0.0243(10) -0.0289(11) C38 0.0472(15) 0.0464(15) 0.0396(12) -0.0055(10) -0.0105(11) -0.0173(13) C18 0.0473(14) 0.0378(14) 0.0403(13) 0.0020(10) -0.0057(10) -0.0092(12) C35 0.0491(15) 0.0529(17) 0.0473(15) -0.0056(12) -0.0050(11) -0.0199(13) C9 0.0568(15) 0.0418(14) 0.0369(13) -0.0055(11) -0.0001(11) -0.0106(12) C6 0.0383(12) 0.0363(13) 0.0465(13) -0.0020(10) -0.0029(10) -0.0128(11) C33 0.0453(13) 0.0398(14) 0.0458(13) -0.0087(10) -0.0068(11) -0.0099(12) C40 0.0516(16) 0.0495(15) 0.0423(13) -0.0076(11) -0.0141(12) -0.0146(13) C39 0.0448(14) 0.0411(13) 0.0378(12) -0.0039(10) -0.0147(10) -0.0126(11) O7 0.1389(17) 0.1069(15) 0.0969(14) 0.0411(10) -0.0696(13) -0.0886(14) N11 0.0441(12) 0.0667(14) 0.0550(12) -0.0218(10) -0.0119(9) -0.0049(10) C47 0.0443(13) 0.0395(14) 0.0454(13) -0.0019(11) -0.0081(10) -0.0111(11) C34 0.0395(13) 0.0364(14) 0.0490(14) -0.0046(10) -0.0058(10) -0.0120(11) C37 0.0453(15) 0.0455(15) 0.0442(13) -0.0049(10) -0.0152(11) -0.0114(12) C32 0.0484(15) 0.0387(14) 0.0558(15) 0.0030(11) -0.0105(12) -0.0129(12) C1 0.0540(14) 0.0436(14) 0.0471(14) -0.0036(11) -0.0045(11) -0.0141(12) C44 0.0541(14) 0.0404(13) 0.0400(13) -0.0013(10) -0.0157(10) -0.0172(12) C52 0.0686(16) 0.0432(15) 0.0569(15) -0.0140(12) 0.0010(12) -0.0168(13) C51 0.0716(17) 0.0593(18) 0.0502(15) -0.0087(13) 0.0089(12) -0.0211(14) C45 0.0712(17) 0.0544(16) 0.0489(14) 0.0012(12) -0.0220(13) -0.0268(14) C21 0.0510(15) 0.0373(14) 0.0503(14) -0.0043(10) -0.0056(12) -0.0040(12) C19 0.0583(16) 0.0521(16) 0.0458(15) 0.0011(12) -0.0154(12) -0.0100(14) C48 0.0717(17) 0.0462(16) 0.0543(15) -0.0023(13) 0.0048(12) -0.0020(13) C5 0.0763(17) 0.0450(16) 0.0675(16) 0.0041(13) -0.0219(13) -0.0188(14) C10 0.0890(18) 0.0584(16) 0.0664(15) -0.0196(12) 0.0056(13) -0.0402(15) C31 0.0499(16) 0.0567(17) 0.0749(18) 0.0043(13) -0.0076(13) -0.0115(14) O3 0.1267(17) 0.1063(17) 0.0545(11) -0.0263(10) -0.0343(11) 0.0519(14) C49 0.100(2) 0.0401(16) 0.0751(18) -0.0002(14) 0.0033(16) -0.0031(15) C27 0.0559(16) 0.0736(19) 0.0653(17) 0.0152(14) -0.0082(14) -0.0017(14) C22 0.0586(17) 0.0652(17) 0.0688(16) -0.0198(13) 0.0019(13) -0.0135(14) C2 0.0665(16) 0.0690(19) 0.0537(15) -0.0196(14) 0.0013(12) -0.0246(15) C50 0.0786(18) 0.0499(17) 0.0604(16) 0.0053(13) 0.0038(13) -0.0104(14) C25 0.081(2) 0.097(2) 0.091(2) -0.0374(17) -0.0228(18) -0.0125(18) C14 0.0590(16) 0.089(2) 0.0647(17) 0.0233(14) -0.0133(13) -0.0062(15) C36 0.0790(18) 0.094(2) 0.0520(15) 0.0039(14) -0.0252(14) -0.0117(16) C4 0.089(2) 0.0377(16) 0.103(2) -0.0079(15) -0.0200(17) -0.0156(14) C3 0.0721(18) 0.0561(19) 0.087(2) -0.0333(15) 0.0008(15) -0.0220(15) C42 0.0660(17) 0.100(2) 0.0661(16) -0.0420(15) -0.0092(13) -0.0079(15) C26 0.0591(17) 0.0810(19) 0.0762(18) -0.0267(15) -0.0035(14) -0.0117(15) C30 0.0506(17) 0.076(2) 0.100(2) 0.0176(17) -0.0252(17) -0.0083(15) C41 0.0494(16) 0.093(2) 0.0937(19) -0.0317(15) -0.0178(14) -0.0031(15) C46 0.134(2) 0.0772(19) 0.0621(16) 0.0234(14) -0.0319(16) -0.0558(19) C20 0.0928(19) 0.100(2) 0.0434(14) -0.0212(14) -0.0019(13) -0.0215(17) C13 0.0508(16) 0.083(2) 0.0942(19) -0.0004(15) 0.0027(14) 0.0079(15) C24 0.093(2) 0.093(2) 0.0644(18) -0.0327(15) -0.0096(17) -0.0032(19) C28 0.078(2) 0.107(2) 0.0618(18) 0.0211(15) -0.0121(15) -0.0070(19) C23 0.0726(19) 0.091(2) 0.0765(19) -0.0286(16) 0.0105(15) -0.0153(17) C29 0.078(2) 0.093(2) 0.079(2) 0.0276(17) -0.0317(18) -0.0178(19) _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 N12 C43 1.356(2) . ? N12 N13 1.3616(19) . ? N12 C47 1.427(2) . ? O4 C19 1.310(2) . ? O4 C20 1.441(2) . ? O6 C35 1.327(2) . ? O6 C36 1.439(2) . ? N1 C8 1.360(2) . ? N1 N2 1.3630(19) . ? N1 C6 1.439(2) . ? O2 C9 1.322(2) . ? O2 C10 1.444(2) . ? C8 C7 1.382(2) . ? C8 C11 1.467(2) . ? N5 N6 1.365(2) . ? N5 C17 1.361(2) . ? N5 C21 1.435(2) . ? C11 C12 1.357(3) . ? C11 C15 1.438(2) . ? O5 C35 1.200(2) . ? N8 C34 1.356(2) . ? N8 N9 1.371(2) . ? N8 C32 1.431(2) . ? N3 N2 1.3102(19) . ? N3 C7 1.364(2) . ? N4 C12 1.338(2) . ? N4 C14 1.448(2) . ? N4 C13 1.456(2) . ? N6 N7 1.303(2) . ? C43 C44 1.372(2) . ? C43 C39 1.482(2) . ? C12 H12 0.958(18) . ? O8 C45 1.320(2) . ? O8 C46 1.433(2) . ? N7 C18 1.357(2) . ? C7 C9 1.467(2) . ? N13 N14 1.298(2) . ? C15 C16 1.336(3) . ? C15 H15 0.948(16) . ? O1 C9 1.199(2) . ? C17 C18 1.390(2) . ? C17 C16 1.436(3) . ? N10 N9 1.300(2) . ? N10 C33 1.364(2) . ? C16 H16 0.961(17) . ? N14 C44 1.361(2) . ? C38 C37 1.326(3) . ? C38 C39 1.438(3) . ? C38 H38 0.963(16) . ? C18 C19 1.464(3) . ? C35 C33 1.452(3) . ? C6 C5 1.363(3) . ? C6 C1 1.372(2) . ? C33 C34 1.392(2) . ? C40 N11 1.336(2) . ? C40 C39 1.358(3) . ? C40 H40 0.981(17) . ? O7 C45 1.191(2) . ? N11 C41 1.451(2) . ? N11 C42 1.442(2) . ? C47 C48 1.367(3) . ? C47 C52 1.369(3) . ? C34 C37 1.447(3) . ? C37 H37 0.959(16) . ? C32 C27 1.370(3) . ? C32 C31 1.371(3) . ? C1 C2 1.374(3) . ? C1 H1A 0.9300 . ? C44 C45 1.461(3) . ? C52 C51 1.377(3) . ? C52 H52A 0.9300 . ? C51 C50 1.358(3) . ? C51 H51A 0.9300 . ? C21 C22 1.357(3) . ? C21 C26 1.377(3) . ? C19 O3 1.181(2) . ? C48 C49 1.375(3) . ? C48 H48A 0.9300 . ? C5 C4 1.380(3) . ? C5 H5A 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C31 C30 1.376(3) . ? C31 H31A 0.9300 . ? C49 C50 1.367(3) . ? C49 H49A 0.9300 . ? C27 C28 1.379(3) . ? C27 H27A 0.9300 . ? C22 C23 1.384(3) . ? C22 H22A 0.9300 . ? C2 C3 1.367(3) . ? C2 H2A 0.9300 . ? C50 H50A 0.9300 . ? C25 C24 1.369(3) . ? C25 C26 1.385(3) . ? C25 H25A 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C4 C3 1.361(3) . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C26 H26A 0.9300 . ? C30 C29 1.356(3) . ? C30 H30A 0.9300 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C24 C23 1.365(3) . ? C24 H24A 0.9300 . ? C28 C29 1.362(3) . ? C28 H28A 0.9300 . ? C23 H23A 0.9300 . ? C29 H29A 0.9300 . ? 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 C43 N12 N13 111.04(15) . . ? C43 N12 C47 130.94(15) . . ? N13 N12 C47 118.01(15) . . ? C19 O4 C20 117.37(18) . . ? C35 O6 C36 117.02(17) . . ? C8 N1 N2 111.65(14) . . ? C8 N1 C6 128.82(16) . . ? N2 N1 C6 119.53(15) . . ? C9 O2 C10 117.09(15) . . ? N1 C8 C7 102.87(17) . . ? N1 C8 C11 122.32(15) . . ? C7 C8 C11 134.77(18) . . ? N6 N5 C17 111.63(15) . . ? N6 N5 C21 118.56(16) . . ? C17 N5 C21 129.61(16) . . ? C12 C11 C15 118.86(19) . . ? C12 C11 C8 124.22(18) . . ? C15 C11 C8 116.73(17) . . ? C34 N8 N9 111.79(16) . . ? C34 N8 C32 130.28(17) . . ? N9 N8 C32 117.84(17) . . ? N2 N3 C7 108.64(15) . . ? C12 N4 C14 124.50(18) . . ? C12 N4 C13 120.06(19) . . ? C14 N4 C13 115.41(18) . . ? N7 N6 N5 106.84(16) . . ? N3 N2 N1 106.96(14) . . ? N12 C43 C44 103.19(15) . . ? N12 C43 C39 122.89(17) . . ? C44 C43 C39 133.90(18) . . ? N4 C12 C11 132.2(2) . . ? N4 C12 H12 111.8(11) . . ? C11 C12 H12 116.0(11) . . ? C45 O8 C46 117.31(17) . . ? N6 N7 C18 109.32(16) . . ? N3 C7 C8 109.88(17) . . ? N3 C7 C9 120.29(17) . . ? C8 C7 C9 129.80(19) . . ? N14 N13 N12 107.34(15) . . ? C16 C15 C11 125.9(2) . . ? C16 C15 H15 119.1(10) . . ? C11 C15 H15 115.0(10) . . ? N5 C17 C18 102.64(16) . . ? N5 C17 C16 120.27(17) . . ? C18 C17 C16 136.82(19) . . ? N9 N10 C33 109.62(16) . . ? C15 C16 C17 127.7(2) . . ? C15 C16 H16 118.9(10) . . ? C17 C16 H16 113.3(10) . . ? N10 N9 N8 106.58(17) . . ? N13 N14 C44 108.62(15) . . ? C37 C38 C39 127.66(19) . . ? C37 C38 H38 117.0(10) . . ? C39 C38 H38 115.4(10) . . ? N7 C18 C17 109.55(17) . . ? N7 C18 C19 120.75(18) . . ? C17 C18 C19 129.70(19) . . ? O5 C35 O6 122.7(2) . . ? O5 C35 C33 125.55(19) . . ? O6 C35 C33 111.8(2) . . ? O1 C9 O2 124.03(19) . . ? O1 C9 C7 124.5(2) . . ? O2 C9 C7 111.43(17) . . ? C5 C6 C1 121.21(18) . . ? C5 C6 N1 118.96(17) . . ? C1 C6 N1 119.82(18) . . ? N10 C33 C34 109.10(17) . . ? N10 C33 C35 120.62(18) . . ? C34 C33 C35 130.20(19) . . ? N11 C40 C39 133.23(19) . . ? N11 C40 H40 111.1(10) . . ? C39 C40 H40 115.6(10) . . ? C40 C39 C38 117.16(17) . . ? C40 C39 C43 124.97(17) . . ? C38 C39 C43 117.87(18) . . ? C40 N11 C41 121.09(16) . . ? C40 N11 C42 123.13(18) . . ? C41 N11 C42 115.72(17) . . ? C48 C47 C52 120.8(2) . . ? C48 C47 N12 118.91(18) . . ? C52 C47 N12 120.07(19) . . ? N8 C34 C33 102.90(16) . . ? N8 C34 C37 122.60(17) . . ? C33 C34 C37 134.4(2) . . ? C38 C37 C34 124.92(19) . . ? C38 C37 H37 121.0(10) . . ? C34 C37 H37 114.0(10) . . ? C27 C32 C31 120.0(2) . . ? C27 C32 N8 120.4(2) . . ? C31 C32 N8 119.6(2) . . ? C6 C1 C2 118.9(2) . . ? C6 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? N14 C44 C43 109.79(18) . . ? N14 C44 C45 121.17(18) . . ? C43 C44 C45 129.01(18) . . ? C47 C52 C51 119.3(2) . . ? C47 C52 H52A 120.3 . . ? C51 C52 H52A 120.3 . . ? C50 C51 C52 120.5(2) . . ? C50 C51 H51A 119.8 . . ? C52 C51 H51A 119.8 . . ? O7 C45 O8 123.6(2) . . ? O7 C45 C44 124.44(19) . . ? O8 C45 C44 111.93(19) . . ? C22 C21 C26 121.5(2) . . ? C22 C21 N5 119.9(2) . . ? C26 C21 N5 118.5(2) . . ? O3 C19 O4 122.4(2) . . ? O3 C19 C18 125.0(2) . . ? O4 C19 C18 112.7(2) . . ? C47 C48 C49 119.0(2) . . ? C47 C48 H48A 120.5 . . ? C49 C48 H48A 120.5 . . ? C6 C5 C4 119.0(2) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C30 C31 C32 119.7(2) . . ? C30 C31 H31A 120.2 . . ? C32 C31 H31A 120.2 . . ? C50 C49 C48 120.8(2) . . ? C50 C49 H49A 119.6 . . ? C48 C49 H49A 119.6 . . ? C28 C27 C32 119.5(2) . . ? C28 C27 H27A 120.2 . . ? C32 C27 H27A 120.2 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H22A 120.2 . . ? C23 C22 H22A 120.2 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C51 C50 C49 119.6(2) . . ? C51 C50 H50A 120.2 . . ? C49 C50 H50A 120.2 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O6 C36 H36A 109.5 . . ? O6 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O6 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? N11 C42 H42A 109.5 . . ? N11 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? N11 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C21 C26 C25 118.5(2) . . ? C21 C26 H26A 120.8 . . ? C25 C26 H26A 120.8 . . ? C29 C30 C31 120.5(2) . . ? C29 C30 H30A 119.8 . . ? C31 C30 H30A 119.8 . . ? N11 C41 H41A 109.5 . . ? N11 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? N11 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O8 C46 H46A 109.5 . . ? O8 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O8 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C13 H13A 109.5 . . ? N4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C23 C24 C25 120.9(2) . . ? C23 C24 H24A 119.6 . . ? C25 C24 H24A 119.6 . . ? C27 C28 C29 120.4(3) . . ? C27 C28 H28A 119.8 . . ? C29 C28 H28A 119.8 . . ? C24 C23 C22 119.4(2) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C30 C29 C28 119.9(2) . . ? C30 C29 H29A 120.0 . . ? C28 C29 H29A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.236 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.032