Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Yun-Ming Wang' _publ_contact_author_address ; Faculty of Medicinal and Applied Chemistry Kaohsiung Medical University 100 Shih-Chuan 1st Road Kaohsiung 807 TAIWAN ; _publ_contact_author_email YMWANG@KMU.EDU.TW _publ_section_title ; Synthesis and characterization of a novel paramagnetic macromolecular complex [Gd(TTDASQ-protamine)] ; loop_ _publ_author_name 'Yun-Ming Wang.' 'Tsan-Hwang Cheng.' 'Michael Y. Chiang' 'Jie-Shiunh Jeng.' ; Wei-Tsung Lee ; 'Gin-Chung Liu.' 'Ching-Ming Wu.' # Attachment 'kmu51.cif' data_kmu51 _database_code_depnum_ccdc_archive 'CCDC 603492' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H56 Br N3 O8' _chemical_formula_sum 'C29 H56 Br N3 O8' _chemical_formula_weight 654.68 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.957(4) _cell_length_b 11.822(3) _cell_length_c 26.391(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.96(2) _cell_angle_gamma 90.00 _cell_volume 3716.7(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 4.42 _cell_measurement_theta_max 7.17 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; The scan width was 1.00+0.35tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7680 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7315 _reflns_number_gt 3772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC (Molecular Structure Corporation, 1992)' _computing_cell_refinement 'MSC/AFC (Molecular Structure Corporation, 1992)' _computing_data_reduction 'teXsan (Molecular Structure Corporation, 1985)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WINGX publication routines (Farrugia, 1999)' _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^)+(0.0300P)^2^+3.0472P] 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 7315 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _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 Br Br 0.38832(3) 0.59377(3) 0.698967(16) 0.07115(14) Uani 1 1 d . . . C1 C 0.3474(3) 0.5609(4) 0.43887(14) 0.0723(12) Uani 1 1 d . . . C2 C 0.4056(4) 0.4650(5) 0.41583(17) 0.1212(19) Uani 1 1 d . . . H2A H 0.4709 0.4445 0.4376 0.182 Uiso 1 1 calc R . . H2B H 0.4277 0.4873 0.3832 0.182 Uiso 1 1 calc R . . H2C H 0.3557 0.4014 0.4119 0.182 Uiso 1 1 calc R . . C3 C 0.2443(4) 0.5994(5) 0.40733(19) 0.128(2) Uani 1 1 d . . . H3A H 0.2108 0.6613 0.4240 0.193 Uiso 1 1 calc R . . H3B H 0.1917 0.5380 0.4032 0.193 Uiso 1 1 calc R . . H3C H 0.2644 0.6234 0.3746 0.193 Uiso 1 1 calc R . . C4 C 0.4283(4) 0.6585(5) 0.45073(18) 0.1133(18) Uani 1 1 d . . . H4A H 0.4928 0.6317 0.4715 0.170 Uiso 1 1 calc R . . H4B H 0.3917 0.7165 0.4686 0.170 Uiso 1 1 calc R . . H4C H 0.4516 0.6888 0.4196 0.170 Uiso 1 1 calc R . . C5 C 0.2487(3) 0.4462(3) 0.49944(13) 0.0579(9) Uani 1 1 d . . . C6 C 0.2582(2) 0.4162(3) 0.55579(11) 0.0513(8) Uani 1 1 d . . . H6A H 0.3182 0.3614 0.5621 0.062 Uiso 1 1 calc R . . H6B H 0.2799 0.4837 0.5751 0.062 Uiso 1 1 calc R . . C7 C 0.1226(3) 0.2613(3) 0.55377(12) 0.0548(8) Uani 1 1 d . . . H7A H 0.1878 0.2206 0.5441 0.066 Uiso 1 1 calc R . . H7B H 0.0721 0.2729 0.5234 0.066 Uiso 1 1 calc R . . C8 C 0.0642(3) 0.1918(3) 0.59166(13) 0.0594(9) Uani 1 1 d . . . C9 C -0.0333(4) 0.0096(3) 0.59948(13) 0.0697(11) Uani 1 1 d . . . C10 C -0.1471(4) 0.0613(4) 0.60638(18) 0.1028(16) Uani 1 1 d . . . H10A H -0.1380 0.1233 0.6299 0.154 Uiso 1 1 calc R . . H10B H -0.1950 0.0052 0.6194 0.154 Uiso 1 1 calc R . . H10C H -0.1802 0.0883 0.5742 0.154 Uiso 1 1 calc R . . C11 C -0.0452(5) -0.0886(4) 0.56266(16) 0.1121(18) Uani 1 1 d . . . H11A H -0.0858 -0.0645 0.5316 0.168 Uiso 1 1 calc R . . H11B H -0.0853 -0.1490 0.5774 0.168 Uiso 1 1 calc R . . H11C H 0.0279 -0.1147 0.5557 0.168 Uiso 1 1 calc R . . C12 C 0.0301(4) -0.0235(4) 0.64929(15) 0.0988(16) Uani 1 1 d . . . H12A H 0.0359 0.0408 0.6716 0.148 Uiso 1 1 calc R . . H12B H 0.1039 -0.0489 0.6431 0.148 Uiso 1 1 calc R . . H12C H -0.0093 -0.0832 0.6648 0.148 Uiso 1 1 calc R . . C13 C 0.0664(3) 0.4533(3) 0.57493(12) 0.0565(9) Uani 1 1 d . . . H13A H -0.0045 0.4136 0.5754 0.068 Uiso 1 1 calc R . . H13B H 0.0640 0.4968 0.5437 0.068 Uiso 1 1 calc R . . C14 C 0.0794(3) 0.5340(3) 0.61988(13) 0.0629(9) Uani 1 1 d . . . H14A H 0.1485 0.5763 0.6183 0.076 Uiso 1 1 calc R . . H14B H 0.0178 0.5876 0.6169 0.076 Uiso 1 1 calc R . . C15 C 0.0816(3) 0.4769(3) 0.67112(12) 0.0591(9) Uani 1 1 d . . . H15A H 0.0741 0.5335 0.6972 0.071 Uiso 1 1 calc R . . H15B H 0.0185 0.4254 0.6713 0.071 Uiso 1 1 calc R . . C16 C 0.1926(3) 0.3409(3) 0.72854(12) 0.0525(8) Uani 1 1 d . . . H16A H 0.1457 0.2747 0.7218 0.063 Uiso 1 1 calc R . . H16B H 0.1641 0.3824 0.7564 0.063 Uiso 1 1 calc R . . C17 C 0.3126(3) 0.3043(3) 0.74328(12) 0.0555(9) Uani 1 1 d . . . H17A H 0.3558 0.3688 0.7567 0.067 Uiso 1 1 calc R . . H17B H 0.3133 0.2475 0.7698 0.067 Uiso 1 1 calc R . . C18 C 0.3409(3) 0.1397(3) 0.69012(12) 0.0581(9) Uani 1 1 d . . . H18A H 0.2637 0.1246 0.6966 0.070 Uiso 1 1 calc R . . H18B H 0.3889 0.0946 0.7138 0.070 Uiso 1 1 calc R . . C19 C 0.3583(3) 0.1034(4) 0.63670(14) 0.0628(9) Uani 1 1 d . . . C20 C 0.3816(5) -0.0687(4) 0.58655(17) 0.1008(16) Uani 1 1 d . . . C21 C 0.3083(5) -0.0312(4) 0.54033(17) 0.1148(18) Uani 1 1 d . . . H21A H 0.2310 -0.0435 0.5459 0.172 Uiso 1 1 calc R . . H21B H 0.3269 -0.0739 0.5113 0.172 Uiso 1 1 calc R . . H21C H 0.3204 0.0478 0.5344 0.172 Uiso 1 1 calc R . . C22 C 0.3546(8) -0.1894(5) 0.5999(2) 0.221(5) Uani 1 1 d . . . H22A H 0.2758 -0.1959 0.6038 0.331 Uiso 1 1 calc R . . H22B H 0.3967 -0.2100 0.6311 0.331 Uiso 1 1 calc R . . H22C H 0.3741 -0.2388 0.5731 0.331 Uiso 1 1 calc R . . C23 C 0.5043(5) -0.0517(7) 0.5806(2) 0.180(3) Uani 1 1 d . . . H23A H 0.5176 0.0262 0.5727 0.269 Uiso 1 1 calc R . . H23B H 0.5264 -0.0988 0.5536 0.269 Uiso 1 1 calc R . . H23C H 0.5472 -0.0714 0.6118 0.269 Uiso 1 1 calc R . . C24 C 0.4822(3) 0.2894(3) 0.69786(13) 0.0577(9) Uani 1 1 d . . . H24A H 0.4877 0.3712 0.6991 0.069 Uiso 1 1 calc R . . H24B H 0.5062 0.2653 0.6654 0.069 Uiso 1 1 calc R . . C25 C 0.5629(3) 0.2410(3) 0.73967(14) 0.0566(9) Uani 1 1 d . . . C26 C 0.7669(3) 0.2300(3) 0.76321(14) 0.0596(9) Uani 1 1 d . . . C27 C 0.7736(3) 0.1032(3) 0.76154(18) 0.0875(13) Uani 1 1 d . . . H27A H 0.7111 0.0713 0.7771 0.131 Uiso 1 1 calc R . . H27B H 0.8424 0.0786 0.7796 0.131 Uiso 1 1 calc R . . H27C H 0.7716 0.0786 0.7268 0.131 Uiso 1 1 calc R . . C28 C 0.8632(3) 0.2835(4) 0.73825(17) 0.0845(13) Uani 1 1 d . . . H28A H 0.8571 0.3644 0.7398 0.127 Uiso 1 1 calc R . . H28B H 0.8606 0.2600 0.7034 0.127 Uiso 1 1 calc R . . H28C H 0.9331 0.2601 0.7558 0.127 Uiso 1 1 calc R . . C29 C 0.7613(4) 0.2746(4) 0.81647(16) 0.0913(13) Uani 1 1 d . . . H29A H 0.6997 0.2398 0.8315 0.137 Uiso 1 1 calc R . . H29B H 0.7507 0.3551 0.8153 0.137 Uiso 1 1 calc R . . H29C H 0.8301 0.2573 0.8365 0.137 Uiso 1 1 calc R . . N1 N 0.1574(2) 0.3703(2) 0.57515(9) 0.0460(6) Uani 1 1 d . . . N2 N 0.1880(2) 0.4132(3) 0.68273(10) 0.0461(6) Uani 1 1 d . . . N3 N 0.3647(2) 0.2582(2) 0.69966(10) 0.0529(7) Uani 1 1 d . . . O1 O 0.32221(18) 0.5260(2) 0.49093(8) 0.0611(6) Uani 1 1 d . . . O2 O 0.1846(3) 0.4027(3) 0.46808(10) 0.0986(10) Uani 1 1 d . . . O3 O 0.0322(2) 0.0924(2) 0.57165(8) 0.0677(7) Uani 1 1 d . . . O4 O 0.0482(2) 0.2217(2) 0.63376(9) 0.0838(9) Uani 1 1 d . . . O5 O 0.66777(17) 0.2694(2) 0.73045(9) 0.0611(6) Uani 1 1 d . . . O6 O 0.53787(19) 0.1865(2) 0.77525(10) 0.0802(8) Uani 1 1 d . . . O7 O 0.3532(3) -0.0079(2) 0.63291(10) 0.0851(8) Uani 1 1 d . . . O8 O 0.3769(3) 0.1660(2) 0.60227(10) 0.0873(9) Uani 1 1 d . . . H2D H 0.249(3) 0.465(3) 0.6834(12) 0.065(10) Uiso 1 1 d . . . H2E H 0.199(2) 0.370(2) 0.6568(11) 0.035(8) 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 Br 0.0607(2) 0.0619(2) 0.0913(3) -0.0104(2) 0.00936(19) -0.0152(2) C1 0.054(2) 0.109(3) 0.056(2) 0.031(2) 0.0153(18) -0.004(2) C2 0.136(4) 0.166(5) 0.069(3) 0.009(3) 0.046(3) 0.027(4) C3 0.066(3) 0.196(6) 0.122(4) 0.100(4) -0.001(3) 0.002(3) C4 0.102(4) 0.142(5) 0.098(4) 0.045(3) 0.024(3) -0.044(3) C5 0.050(2) 0.071(2) 0.053(2) 0.0113(19) 0.0075(17) -0.0095(18) C6 0.0429(17) 0.065(2) 0.0461(18) 0.0075(17) 0.0040(14) -0.0079(16) C7 0.065(2) 0.056(2) 0.0434(19) -0.0001(16) 0.0073(16) -0.0139(17) C8 0.072(2) 0.060(2) 0.045(2) -0.0029(18) 0.0002(18) -0.0154(18) C9 0.096(3) 0.066(2) 0.047(2) 0.0033(19) 0.005(2) -0.035(2) C10 0.093(3) 0.115(4) 0.100(4) 0.011(3) 0.009(3) -0.038(3) C11 0.186(5) 0.082(3) 0.069(3) -0.004(3) 0.008(3) -0.060(3) C12 0.130(4) 0.095(3) 0.068(3) 0.024(3) -0.012(3) -0.039(3) C13 0.0431(18) 0.071(2) 0.055(2) 0.0073(18) -0.0018(15) -0.0016(17) C14 0.055(2) 0.062(2) 0.072(2) 0.002(2) 0.0014(18) 0.0113(17) C15 0.052(2) 0.070(2) 0.055(2) -0.0081(19) 0.0046(16) 0.0078(18) C16 0.055(2) 0.060(2) 0.0426(19) 0.0011(16) 0.0103(15) -0.0086(16) C17 0.0514(19) 0.071(2) 0.0428(19) 0.0041(17) -0.0042(15) -0.0113(17) C18 0.053(2) 0.064(2) 0.057(2) 0.0080(18) 0.0017(16) -0.0042(17) C19 0.058(2) 0.075(3) 0.054(2) 0.007(2) -0.0003(17) 0.009(2) C20 0.155(5) 0.081(3) 0.068(3) 0.003(2) 0.017(3) 0.045(3) C21 0.153(5) 0.110(4) 0.078(3) -0.019(3) -0.008(3) 0.033(4) C22 0.479(15) 0.073(4) 0.119(5) 0.003(4) 0.071(7) 0.054(6) C23 0.136(6) 0.271(10) 0.133(5) -0.035(6) 0.020(4) 0.096(6) C24 0.0474(19) 0.065(2) 0.060(2) 0.0178(18) 0.0040(16) -0.0062(17) C25 0.0423(19) 0.063(2) 0.064(2) 0.0088(19) -0.0012(17) -0.0030(16) C26 0.0427(19) 0.057(2) 0.078(3) 0.0093(19) 0.0000(17) 0.0065(16) C27 0.078(3) 0.064(3) 0.120(4) 0.006(3) 0.004(3) 0.006(2) C28 0.043(2) 0.090(3) 0.121(4) 0.020(3) 0.008(2) 0.004(2) C29 0.078(3) 0.107(4) 0.087(3) -0.012(3) -0.006(2) -0.003(3) N1 0.0406(14) 0.0530(16) 0.0446(15) 0.0025(12) 0.0063(11) -0.0061(12) N2 0.0419(15) 0.0502(16) 0.0462(16) -0.0068(15) 0.0041(12) -0.0062(14) N3 0.0445(16) 0.0624(18) 0.0520(16) 0.0060(14) 0.0066(13) -0.0048(13) O1 0.0531(13) 0.0799(17) 0.0519(14) 0.0122(12) 0.0135(11) -0.0113(13) O2 0.104(2) 0.135(3) 0.0547(16) 0.0171(17) -0.0033(15) -0.059(2) O3 0.0992(19) 0.0626(15) 0.0418(13) -0.0041(12) 0.0084(12) -0.0325(14) O4 0.124(2) 0.0830(19) 0.0476(15) -0.0131(14) 0.0243(15) -0.0476(17) O5 0.0412(13) 0.0709(16) 0.0711(15) 0.0181(13) 0.0040(11) -0.0002(11) O6 0.0547(15) 0.110(2) 0.0752(18) 0.0440(17) 0.0018(13) -0.0129(15) O7 0.133(3) 0.0599(18) 0.0638(17) 0.0093(14) 0.0194(16) 0.0149(17) O8 0.129(3) 0.079(2) 0.0545(17) 0.0124(15) 0.0097(16) -0.0053(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.487(6) . ? C1 O1 1.490(4) . ? C1 C3 1.497(5) . ? C1 C4 1.521(6) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 O2 1.196(4) . ? C5 O1 1.321(4) . ? C5 C6 1.524(4) . ? C6 N1 1.454(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N1 1.453(4) . ? C7 C8 1.511(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O4 1.197(4) . ? C8 O3 1.331(4) . ? C9 O3 1.487(4) . ? C9 C12 1.511(5) . ? C9 C11 1.513(5) . ? C9 C10 1.517(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N1 1.465(4) . ? C13 C14 1.519(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.509(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N2 1.487(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N2 1.478(4) . ? C16 C17 1.517(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N3 1.461(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N3 1.447(4) . ? C18 C19 1.505(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 O8 1.208(4) . ? C19 O7 1.321(4) . ? C20 O7 1.484(5) . ? C20 C23 1.501(8) . ? C20 C21 1.506(6) . ? C20 C22 1.510(7) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N3 1.458(4) . ? C24 C25 1.514(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O6 1.198(4) . ? C25 O5 1.341(4) . ? C26 O5 1.480(4) . ? C26 C27 1.503(5) . ? C26 C29 1.508(5) . ? C26 C28 1.514(5) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N2 H2D 0.95(4) . ? N2 H2E 0.87(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O1 107.7(3) . . ? C2 C1 C3 113.3(4) . . ? O1 C1 C3 112.0(3) . . ? C2 C1 C4 110.5(4) . . ? O1 C1 C4 101.3(3) . . ? C3 C1 C4 111.3(4) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 O1 125.9(3) . . ? O2 C5 C6 124.4(3) . . ? O1 C5 C6 109.7(3) . . ? N1 C6 C5 115.8(3) . . ? N1 C6 H6A 108.3 . . ? C5 C6 H6A 108.3 . . ? N1 C6 H6B 108.3 . . ? C5 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? N1 C7 C8 111.0(3) . . ? N1 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O4 C8 O3 124.5(3) . . ? O4 C8 C7 125.0(3) . . ? O3 C8 C7 110.5(3) . . ? O3 C9 C12 110.7(3) . . ? O3 C9 C11 102.2(3) . . ? C12 C9 C11 111.9(4) . . ? O3 C9 C10 108.1(3) . . ? C12 C9 C10 112.8(4) . . ? C11 C9 C10 110.6(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 113.0(3) . . ? N1 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N1 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 114.3(3) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N2 C15 C14 111.1(3) . . ? N2 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C17 110.0(2) . . ? N2 C16 H16A 109.7 . . ? C17 C16 H16A 109.7 . . ? N2 C16 H16B 109.7 . . ? C17 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? N3 C17 C16 111.3(3) . . ? N3 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? N3 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? N3 C18 C19 113.5(3) . . ? N3 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? N3 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? O8 C19 O7 124.3(4) . . ? O8 C19 C18 125.4(4) . . ? O7 C19 C18 110.2(3) . . ? O7 C20 C23 108.4(5) . . ? O7 C20 C21 111.5(4) . . ? C23 C20 C21 112.4(5) . . ? O7 C20 C22 101.4(4) . . ? C23 C20 C22 112.5(5) . . ? C21 C20 C22 110.2(5) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C25 115.9(3) . . ? N3 C24 H24A 108.3 . . ? C25 C24 H24A 108.3 . . ? N3 C24 H24B 108.3 . . ? C25 C24 H24B 108.3 . . ? H24A C24 H24B 107.4 . . ? O6 C25 O5 125.3(3) . . ? O6 C25 C24 126.0(3) . . ? O5 C25 C24 108.7(3) . . ? O5 C26 C27 109.8(3) . . ? O5 C26 C29 109.7(3) . . ? C27 C26 C29 112.5(4) . . ? O5 C26 C28 102.4(3) . . ? C27 C26 C28 111.0(3) . . ? C29 C26 C28 110.9(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 N1 C7 114.4(3) . . ? C6 N1 C13 112.8(3) . . ? C7 N1 C13 113.8(3) . . ? C16 N2 C15 115.6(3) . . ? C16 N2 H2D 112.7(19) . . ? C15 N2 H2D 108(2) . . ? C16 N2 H2E 107.9(18) . . ? C15 N2 H2E 108.6(18) . . ? H2D N2 H2E 103(3) . . ? C18 N3 C24 114.5(3) . . ? C18 N3 C17 114.1(3) . . ? C24 N3 C17 114.1(3) . . ? C5 O1 C1 123.0(3) . . ? C8 O3 C9 122.1(3) . . ? C25 O5 C26 122.0(3) . . ? C19 O7 C20 122.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.239 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.048