# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hirohito Tsue' _publ_contact_author_email tsue@ger.mbox.media.kyoto-u.ac.jp _publ_author_name 'Hirohito Tsue' data_cmpd_2 _database_code_depnum_ccdc_archive 'CCDC 841915' #TrackingRef '6923_web_deposit_cif_file_0_HirohitoTsue_ #1314588024.tsue110829.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H60 N4 O4' _chemical_formula_weight 708.96 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 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 12.774(4) _cell_length_b 16.152(5) _cell_length_c 21.355(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.427(4) _cell_angle_gamma 90.00 _cell_volume 4319(2) _cell_formula_units_Z 4 _cell_measurement_temperature 133 _cell_measurement_reflns_used 9288 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.6533 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32136 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0749 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9767 _reflns_number_gt 6235 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_cell_refinement ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_data_reduction ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0636P)^2^+2.8646P] 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 9767 _refine_ls_number_parameters 569 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1428 _refine_ls_R_factor_gt 0.0916 _refine_ls_wR_factor_ref 0.2041 _refine_ls_wR_factor_gt 0.1768 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.123 _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 0.5356(2) 0.36007(17) 0.15999(14) 0.0306(6) Uani 1 1 d . . . C2 C 0.6025(2) 0.29182(18) 0.17819(14) 0.0322(6) Uani 1 1 d . . . H1 H 0.678(2) 0.3046(17) 0.1917(13) 0.029(7) Uiso 1 1 d . . . C3 C 0.5624(2) 0.21231(17) 0.18110(13) 0.0307(6) Uani 1 1 d . . . C4 C 0.4512(2) 0.20239(19) 0.16652(14) 0.0326(7) Uani 1 1 d . . . H2 H 0.421(2) 0.1494(19) 0.1702(14) 0.037(8) Uiso 1 1 d . . . C5 C 0.3830(2) 0.26919(17) 0.14861(14) 0.0306(6) Uani 1 1 d . . . C6 C 0.1885(2) 0.30365(16) 0.14270(13) 0.0280(6) Uani 1 1 d . . . C7 C 0.0921(2) 0.30259(17) 0.09849(14) 0.0289(6) Uani 1 1 d . . . H3 H 0.087(2) 0.2718(16) 0.0613(13) 0.022(7) Uiso 1 1 d . . . C8 C 0.0019(2) 0.34441(16) 0.10969(13) 0.0277(6) Uani 1 1 d . . . C9 C 0.0118(2) 0.38948(17) 0.16592(13) 0.0275(6) Uani 1 1 d . . . H4 H -0.048(2) 0.4211(17) 0.1745(13) 0.026(7) Uiso 1 1 d . . . C10 C 0.1078(2) 0.39228(16) 0.21075(13) 0.0267(6) Uani 1 1 d . . . C11 C 0.1944(2) 0.48132(16) 0.30457(13) 0.0270(6) Uani 1 1 d . . . C12 C 0.1972(2) 0.48769(17) 0.37021(13) 0.0285(6) Uani 1 1 d . . . H5 H 0.140(2) 0.4578(19) 0.3878(14) 0.043(9) Uiso 1 1 d . . . C13 C 0.2732(2) 0.53541(16) 0.41001(12) 0.0275(6) Uani 1 1 d . . . C14 C 0.3495(2) 0.57559(17) 0.38258(13) 0.0282(6) Uani 1 1 d . . . H6 H 0.405(2) 0.6059(17) 0.4080(13) 0.027(7) Uiso 1 1 d . . . C15 C 0.3476(2) 0.57138(17) 0.31649(13) 0.0285(6) Uani 1 1 d . . . C16 C 0.4639(2) 0.60639(17) 0.23661(13) 0.0289(6) Uani 1 1 d . . . C17 C 0.4808(2) 0.67371(19) 0.19901(14) 0.0320(7) Uani 1 1 d . . . H7 H 0.458(2) 0.7267(18) 0.2114(13) 0.028(7) Uiso 1 1 d . . . C18 C 0.5299(2) 0.66442(18) 0.14711(14) 0.0333(7) Uani 1 1 d . A . C19 C 0.5589(2) 0.58464(19) 0.13197(15) 0.0338(7) Uani 1 1 d . . . H8 H 0.590(2) 0.5765(17) 0.0947(14) 0.031(8) Uiso 1 1 d . . . C20 C 0.5432(2) 0.51622(17) 0.16855(14) 0.0308(6) Uani 1 1 d . . . C21 C 0.4255(2) 0.34806(17) 0.14368(13) 0.0297(6) Uani 1 1 d . . . C22 C 0.1957(2) 0.34789(16) 0.19949(13) 0.0259(6) Uani 1 1 d . . . C23 C 0.2684(2) 0.52536(17) 0.27754(12) 0.0270(6) Uani 1 1 d . . . C24 C 0.4965(2) 0.52731(17) 0.22202(13) 0.0275(6) Uani 1 1 d . . . C25 C 0.3382(3) 0.4275(2) 0.05690(16) 0.0602(11) Uani 1 1 d . . . H9 H 0.3058 0.3777 0.0351 0.090 Uiso 1 1 calc R . . H10 H 0.4057 0.4393 0.0434 0.090 Uiso 1 1 calc R . . H11 H 0.2895 0.4745 0.0459 0.090 Uiso 1 1 calc R . . C26 C 0.6342(2) 0.13715(18) 0.20154(16) 0.0380(7) Uani 1 1 d . . . C27 C 0.6152(3) 0.1051(2) 0.26597(19) 0.0597(10) Uani 1 1 d . . . H12 H 0.5398 0.0902 0.2621 0.090 Uiso 1 1 calc R . . H13 H 0.6340 0.1484 0.2984 0.090 Uiso 1 1 calc R . . H14 H 0.6598 0.0562 0.2786 0.090 Uiso 1 1 calc R . . C28 C 0.6073(3) 0.0680(2) 0.1513(2) 0.0602(11) Uani 1 1 d . . . H15 H 0.6188 0.0883 0.1099 0.090 Uiso 1 1 calc R . . H16 H 0.5324 0.0516 0.1474 0.090 Uiso 1 1 calc R . . H17 H 0.6535 0.0201 0.1645 0.090 Uiso 1 1 calc R . . C29 C 0.7527(3) 0.1576(2) 0.2086(2) 0.0566(10) Uani 1 1 d . . . H18 H 0.7725 0.2002 0.2415 0.085 Uiso 1 1 calc R . . H19 H 0.7663 0.1782 0.1678 0.085 Uiso 1 1 calc R . . H20 H 0.7952 0.1077 0.2210 0.085 Uiso 1 1 calc R . . C30 C 0.2987(3) 0.2799(2) 0.28707(17) 0.0563(10) Uani 1 1 d . . . H21 H 0.2846 0.2285 0.2624 0.084 Uiso 1 1 calc R . . H22 H 0.2467 0.2858 0.3149 0.084 Uiso 1 1 calc R . . H23 H 0.3710 0.2782 0.3132 0.084 Uiso 1 1 calc R . . C31 C -0.1012(2) 0.34269(18) 0.05893(14) 0.0338(7) Uani 1 1 d . . . C32 C -0.1940(3) 0.3858(3) 0.08115(19) 0.0631(11) Uani 1 1 d . . . H24 H -0.1767 0.4444 0.0893 0.095 Uiso 1 1 calc R . . H25 H -0.2062 0.3596 0.1205 0.095 Uiso 1 1 calc R . . H26 H -0.2587 0.3810 0.0479 0.095 Uiso 1 1 calc R . . C33 C -0.0837(3) 0.3872(3) -0.00038(19) 0.0851(16) Uani 1 1 d . . . H27 H -0.0274 0.3591 -0.0175 0.128 Uiso 1 1 calc R . . H28 H -0.0622 0.4445 0.0104 0.128 Uiso 1 1 calc R . . H29 H -0.1501 0.3869 -0.0325 0.128 Uiso 1 1 calc R . . C34 C -0.1342(3) 0.2529(2) 0.0428(2) 0.0807(15) Uani 1 1 d . . . H30 H -0.1410 0.2235 0.0820 0.121 Uiso 1 1 calc R . . H31 H -0.0799 0.2257 0.0234 0.121 Uiso 1 1 calc R . . H32 H -0.2030 0.2519 0.0127 0.121 Uiso 1 1 calc R . . C35 C 0.1882(3) 0.5677(2) 0.17219(15) 0.0473(9) Uani 1 1 d . . . H33 H 0.2205 0.6190 0.1604 0.071 Uiso 1 1 calc R . . H34 H 0.1304 0.5812 0.1945 0.071 Uiso 1 1 calc R . . H35 H 0.1594 0.5359 0.1336 0.071 Uiso 1 1 calc R . . C36 C 0.2739(2) 0.53868(18) 0.48178(13) 0.0341(7) Uani 1 1 d . . . C37 C 0.3135(3) 0.4555(2) 0.51178(16) 0.0539(10) Uani 1 1 d . . . H36 H 0.3872 0.4463 0.5068 0.081 Uiso 1 1 calc R . . H37 H 0.2678 0.4110 0.4905 0.081 Uiso 1 1 calc R . . H38 H 0.3108 0.4561 0.5573 0.081 Uiso 1 1 calc R . . C38 C 0.1589(3) 0.5534(2) 0.49247(16) 0.0490(9) Uani 1 1 d . . . H39 H 0.1136 0.5063 0.4756 0.074 Uiso 1 1 calc R . . H40 H 0.1301 0.6041 0.4703 0.074 Uiso 1 1 calc R . . H41 H 0.1601 0.5592 0.5383 0.074 Uiso 1 1 calc R . . C39 C 0.3433(3) 0.6085(2) 0.51580(14) 0.0473(9) Uani 1 1 d . . . H42 H 0.3186 0.6615 0.4959 0.071 Uiso 1 1 calc R . . H43 H 0.4178 0.5993 0.5123 0.071 Uiso 1 1 calc R . . H44 H 0.3380 0.6094 0.5610 0.071 Uiso 1 1 calc R . . C40 C 0.5703(3) 0.4443(2) 0.30930(18) 0.0658(12) Uani 1 1 d . . . H45 H 0.5844 0.4928 0.3373 0.099 Uiso 1 1 calc R . . H46 H 0.6332 0.4325 0.2910 0.099 Uiso 1 1 calc R . . H47 H 0.5546 0.3965 0.3341 0.099 Uiso 1 1 calc R . . C41 C 0.5476(3) 0.7383(2) 0.10491(17) 0.0480(9) Uani 1 1 d D . . C42 C 0.4337(10) 0.7802(7) 0.0807(5) 0.034(3) Uani 0.26 1 d P A 2 H48 H 0.3842 0.7391 0.0575 0.051 Uiso 0.26 1 calc PR A 2 H49 H 0.4409 0.8265 0.0522 0.051 Uiso 0.26 1 calc PR A 2 H50 H 0.4060 0.8006 0.1174 0.051 Uiso 0.26 1 calc PR A 2 C43 C 0.6122(10) 0.8087(6) 0.1536(6) 0.035(3) Uani 0.26 1 d PD A 2 H51 H 0.6087 0.8621 0.1315 0.053 Uiso 0.26 1 calc PR A 2 H52 H 0.6870 0.7920 0.1672 0.053 Uiso 0.26 1 calc PR A 2 H53 H 0.5793 0.8139 0.1912 0.053 Uiso 0.26 1 calc PR A 2 C44 C 0.5983(12) 0.7248(7) 0.0547(7) 0.040(3) Uani 0.26 1 d P A 2 H54 H 0.6031 0.7771 0.0321 0.060 Uiso 0.26 1 calc PR A 2 H55 H 0.5576 0.6845 0.0252 0.060 Uiso 0.26 1 calc PR A 2 H56 H 0.6703 0.7033 0.0709 0.060 Uiso 0.26 1 calc PR A 2 C45 C 0.5217(6) 0.8178(3) 0.1278(4) 0.088(2) Uani 0.74 1 d P A 1 H57 H 0.5343 0.8608 0.0978 0.132 Uiso 0.74 1 calc PR A 1 H58 H 0.5667 0.8283 0.1698 0.132 Uiso 0.74 1 calc PR A 1 H59 H 0.4464 0.8185 0.1313 0.132 Uiso 0.74 1 calc PR A 1 C46 C 0.6636(5) 0.7357(3) 0.0930(3) 0.0581(15) Uani 0.74 1 d P A 1 H60 H 0.6735 0.7805 0.0638 0.087 Uiso 0.74 1 calc PR A 1 H61 H 0.6763 0.6823 0.0740 0.087 Uiso 0.74 1 calc PR A 1 H62 H 0.7141 0.7427 0.1336 0.087 Uiso 0.74 1 calc PR A 1 C47 C 0.4773(5) 0.7219(4) 0.0348(3) 0.0784(18) Uani 0.74 1 d P A 1 H63 H 0.4988 0.6693 0.0182 0.118 Uiso 0.74 1 calc PR A 1 H64 H 0.4888 0.7670 0.0062 0.118 Uiso 0.74 1 calc PR A 1 H65 H 0.4015 0.7194 0.0371 0.118 Uiso 0.74 1 calc PR A 1 O1 O 0.35808(15) 0.41460(12) 0.12410(9) 0.0338(5) Uani 1 1 d . . . O2 O 0.28978(15) 0.34827(12) 0.24462(9) 0.0331(5) Uani 1 1 d . . . O3 O 0.26716(16) 0.51989(13) 0.21304(9) 0.0349(5) Uani 1 1 d . . . O4 O 0.48160(16) 0.46056(12) 0.25951(9) 0.0333(5) Uani 1 1 d . . . N2 N 0.1102(2) 0.43578(16) 0.26773(12) 0.0341(6) Uani 1 1 d . . . H67 H 0.050(3) 0.438(2) 0.2815(16) 0.052(10) Uiso 1 1 d . . . N4 N 0.5822(2) 0.43866(15) 0.15440(13) 0.0368(6) Uani 1 1 d . . . H69 H 0.642(3) 0.4386(19) 0.1389(15) 0.046(9) Uiso 1 1 d . . . N1 N 0.2734(2) 0.25500(16) 0.12952(13) 0.0372(6) Uani 1 1 d . . . H66 H 0.258(2) 0.2081(18) 0.1214(13) 0.022(8) Uiso 1 1 d . . . N3 N 0.4220(2) 0.61978(16) 0.29190(12) 0.0348(6) Uani 1 1 d . . . H68 H 0.434(2) 0.6690(19) 0.3104(14) 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 C1 0.0334(16) 0.0252(14) 0.0355(16) -0.0019(12) 0.0123(13) 0.0015(12) C2 0.0238(14) 0.0336(16) 0.0394(17) -0.0008(13) 0.0067(13) 0.0047(13) C3 0.0303(15) 0.0276(15) 0.0348(15) -0.0018(12) 0.0076(13) 0.0035(12) C4 0.0291(15) 0.0278(16) 0.0413(17) -0.0052(13) 0.0080(13) 0.0005(13) C5 0.0237(14) 0.0311(15) 0.0357(16) -0.0060(12) 0.0027(12) 0.0016(12) C6 0.0234(13) 0.0237(14) 0.0356(15) -0.0035(12) 0.0029(12) 0.0018(11) C7 0.0311(15) 0.0251(14) 0.0292(15) -0.0076(12) 0.0025(12) -0.0011(12) C8 0.0253(14) 0.0253(14) 0.0314(15) 0.0002(12) 0.0032(12) -0.0037(11) C9 0.0222(13) 0.0273(15) 0.0334(15) -0.0021(12) 0.0067(12) -0.0011(12) C10 0.0269(14) 0.0259(14) 0.0277(14) -0.0008(11) 0.0064(12) -0.0055(11) C11 0.0270(14) 0.0275(14) 0.0271(14) -0.0048(11) 0.0067(11) -0.0008(12) C12 0.0308(15) 0.0266(15) 0.0286(14) -0.0008(12) 0.0074(12) -0.0022(12) C13 0.0351(15) 0.0237(14) 0.0236(13) 0.0006(11) 0.0055(12) 0.0056(12) C14 0.0303(15) 0.0266(15) 0.0266(14) -0.0023(12) 0.0033(12) 0.0002(12) C15 0.0290(14) 0.0271(14) 0.0305(15) -0.0018(12) 0.0085(12) -0.0030(12) C16 0.0260(14) 0.0321(15) 0.0294(14) -0.0005(12) 0.0078(12) -0.0065(12) C17 0.0284(15) 0.0278(16) 0.0416(17) -0.0014(13) 0.0114(13) -0.0007(12) C18 0.0291(15) 0.0323(16) 0.0414(17) 0.0040(13) 0.0141(13) -0.0016(13) C19 0.0333(16) 0.0365(17) 0.0364(16) 0.0034(13) 0.0183(14) -0.0005(13) C20 0.0235(14) 0.0306(15) 0.0390(16) 0.0009(13) 0.0079(12) 0.0001(12) C21 0.0271(14) 0.0283(15) 0.0338(15) -0.0030(12) 0.0066(12) 0.0053(12) C22 0.0233(13) 0.0234(13) 0.0291(14) 0.0012(11) 0.0004(11) -0.0025(11) C23 0.0297(14) 0.0325(15) 0.0204(13) -0.0026(11) 0.0085(11) -0.0041(12) C24 0.0251(14) 0.0269(14) 0.0306(14) 0.0030(12) 0.0056(12) -0.0049(12) C25 0.071(3) 0.065(2) 0.043(2) 0.0068(18) 0.0045(19) 0.028(2) C26 0.0283(15) 0.0326(16) 0.052(2) 0.0026(14) 0.0059(14) 0.0060(13) C27 0.055(2) 0.053(2) 0.070(3) 0.021(2) 0.012(2) 0.0116(19) C28 0.050(2) 0.044(2) 0.082(3) -0.015(2) 0.003(2) 0.0197(17) C29 0.0322(18) 0.045(2) 0.092(3) 0.013(2) 0.0112(19) 0.0121(16) C30 0.046(2) 0.062(2) 0.052(2) 0.0237(19) -0.0107(17) -0.0047(18) C31 0.0257(15) 0.0376(16) 0.0355(16) -0.0037(13) -0.0002(13) -0.0012(13) C32 0.038(2) 0.080(3) 0.066(3) -0.017(2) -0.0021(18) 0.013(2) C33 0.051(2) 0.148(5) 0.050(2) 0.035(3) -0.003(2) 0.011(3) C34 0.050(2) 0.059(3) 0.115(4) -0.026(3) -0.028(2) -0.006(2) C35 0.067(2) 0.0438(19) 0.0274(16) 0.0030(14) 0.0009(16) -0.0048(17) C36 0.0466(18) 0.0305(15) 0.0254(14) -0.0010(12) 0.0079(13) 0.0003(14) C37 0.085(3) 0.0410(19) 0.0347(18) 0.0078(15) 0.0102(18) 0.0143(19) C38 0.056(2) 0.060(2) 0.0352(18) -0.0076(16) 0.0191(16) 0.0016(18) C39 0.067(2) 0.047(2) 0.0259(16) -0.0038(14) 0.0063(16) -0.0096(18) C40 0.078(3) 0.056(2) 0.048(2) 0.0213(18) -0.025(2) -0.021(2) C41 0.050(2) 0.0388(19) 0.060(2) 0.0163(16) 0.0230(18) 0.0017(16) C42 0.061(8) 0.017(5) 0.027(6) 0.004(4) 0.016(6) 0.003(5) C43 0.041(7) 0.018(5) 0.056(8) 0.005(5) 0.033(6) -0.005(5) C44 0.058(9) 0.022(6) 0.048(8) 0.006(6) 0.028(7) 0.000(6) C45 0.132(6) 0.035(3) 0.126(6) 0.023(3) 0.099(6) 0.021(4) C46 0.063(4) 0.047(3) 0.076(4) 0.017(3) 0.043(3) 0.002(3) C47 0.085(4) 0.077(4) 0.070(4) 0.036(3) 0.008(3) 0.009(3) O1 0.0317(11) 0.0327(11) 0.0365(11) -0.0002(9) 0.0056(9) 0.0095(9) O2 0.0251(10) 0.0358(11) 0.0349(11) 0.0006(9) -0.0029(9) -0.0024(9) O3 0.0366(11) 0.0469(13) 0.0225(10) -0.0037(9) 0.0090(9) -0.0079(10) O4 0.0379(11) 0.0300(10) 0.0314(11) 0.0053(8) 0.0054(9) -0.0050(9) N2 0.0265(13) 0.0448(15) 0.0334(14) -0.0125(11) 0.0118(11) -0.0107(11) N4 0.0325(14) 0.0292(13) 0.0540(17) 0.0026(12) 0.0213(13) 0.0015(11) N1 0.0279(13) 0.0248(14) 0.0554(17) -0.0160(12) 0.0002(12) 0.0018(11) N3 0.0426(15) 0.0304(14) 0.0354(14) -0.0093(11) 0.0171(12) -0.0138(12) _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 C21 1.394(4) . ? C1 C2 1.401(4) . ? C1 N4 1.417(4) . ? C2 C3 1.388(4) . ? C2 H1 0.97(3) . ? C3 C4 1.401(4) . ? C3 C26 1.532(4) . ? C4 C5 1.392(4) . ? C4 H2 0.95(3) . ? C5 C21 1.397(4) . ? C5 N1 1.397(4) . ? C6 C22 1.395(4) . ? C6 C7 1.396(4) . ? C6 N1 1.412(3) . ? C7 C8 1.396(4) . ? C7 H3 0.93(3) . ? C8 C9 1.389(4) . ? C8 C31 1.532(4) . ? C9 C10 1.399(4) . ? C9 H4 0.97(3) . ? C10 C22 1.393(4) . ? C10 N2 1.400(3) . ? C11 C23 1.397(4) . ? C11 C12 1.399(4) . ? C11 N2 1.407(3) . ? C12 C13 1.390(4) . ? C12 H5 1.01(3) . ? C13 C14 1.393(4) . ? C13 C36 1.532(4) . ? C14 C15 1.408(4) . ? C14 H6 0.94(3) . ? C15 C23 1.391(4) . ? C15 N3 1.410(3) . ? C16 C17 1.393(4) . ? C16 C24 1.398(4) . ? C16 N3 1.406(4) . ? C17 C18 1.386(4) . ? C17 H7 0.96(3) . ? C18 C19 1.397(4) . ? C18 C41 1.538(4) . ? C19 C20 1.391(4) . ? C19 H8 0.96(3) . ? C20 C24 1.400(4) . ? C20 N4 1.403(4) . ? C21 O1 1.389(3) . ? C22 O2 1.383(3) . ? C23 O3 1.377(3) . ? C24 O4 1.378(3) . ? C25 O1 1.422(4) . ? C25 H9 0.9800 . ? C25 H10 0.9800 . ? C25 H11 0.9800 . ? C26 C29 1.527(4) . ? C26 C27 1.533(5) . ? C26 C28 1.540(5) . ? C27 H12 0.9800 . ? C27 H13 0.9800 . ? C27 H14 0.9800 . ? C28 H15 0.9800 . ? C28 H16 0.9800 . ? C28 H17 0.9800 . ? C29 H18 0.9800 . ? C29 H19 0.9800 . ? C29 H20 0.9800 . ? C30 O2 1.419(4) . ? C30 H21 0.9800 . ? C30 H22 0.9800 . ? C30 H23 0.9800 . ? C31 C33 1.511(5) . ? C31 C32 1.529(4) . ? C31 C34 1.531(5) . ? C32 H24 0.9800 . ? C32 H25 0.9800 . ? C32 H26 0.9800 . ? C33 H27 0.9800 . ? C33 H28 0.9800 . ? C33 H29 0.9800 . ? C34 H30 0.9800 . ? C34 H31 0.9800 . ? C34 H32 0.9800 . ? C35 O3 1.423(4) . ? C35 H33 0.9800 . ? C35 H34 0.9800 . ? C35 H35 0.9800 . ? C36 C39 1.526(4) . ? C36 C37 1.530(4) . ? C36 C38 1.549(4) . ? C37 H36 0.9800 . ? C37 H37 0.9800 . ? C37 H38 0.9800 . ? C38 H39 0.9800 . ? C38 H40 0.9800 . ? C38 H41 0.9800 . ? C39 H42 0.9800 . ? C39 H43 0.9800 . ? C39 H44 0.9800 . ? C40 O4 1.416(4) . ? C40 H45 0.9800 . ? C40 H46 0.9800 . ? C40 H47 0.9800 . ? C41 C44 1.376(12) . ? C41 C45 1.436(6) . ? C41 C46 1.553(6) . ? C41 C42 1.595(12) . ? C41 C47 1.609(7) . ? C41 C43 1.648(11) . ? C42 H48 0.9800 . ? C42 H49 0.9800 . ? C42 H50 0.9800 . ? C43 H51 0.9800 . ? C43 H52 0.9800 . ? C43 H53 0.9800 . ? C44 H54 0.9800 . ? C44 H55 0.9800 . ? C44 H56 0.9800 . ? C45 H57 0.9800 . ? C45 H58 0.9800 . ? C45 H59 0.9800 . ? C46 H60 0.9800 . ? C46 H61 0.9800 . ? C46 H62 0.9800 . ? C47 H63 0.9800 . ? C47 H64 0.9800 . ? C47 H65 0.9800 . ? N2 H67 0.87(3) . ? N4 H69 0.89(3) . ? N1 H66 0.79(3) . ? N3 H68 0.89(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 C21 C1 C2 119.3(3) . . ? C21 C1 N4 121.6(3) . . ? C2 C1 N4 119.0(3) . . ? C3 C2 C1 122.0(3) . . ? C3 C2 H1 122.4(16) . . ? C1 C2 H1 115.4(16) . . ? C2 C3 C4 117.5(3) . . ? C2 C3 C26 122.7(3) . . ? C4 C3 C26 119.7(3) . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H2 118.4(18) . . ? C3 C4 H2 120.0(18) . . ? C4 C5 C21 119.7(3) . . ? C4 C5 N1 119.3(3) . . ? C21 C5 N1 120.6(3) . . ? C22 C6 C7 119.4(2) . . ? C22 C6 N1 122.5(2) . . ? C7 C6 N1 117.9(2) . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H3 119.3(16) . . ? C6 C7 H3 119.0(16) . . ? C9 C8 C7 117.8(3) . . ? C9 C8 C31 122.6(2) . . ? C7 C8 C31 119.5(2) . . ? C8 C9 C10 121.7(3) . . ? C8 C9 H4 120.1(16) . . ? C10 C9 H4 118.2(16) . . ? C22 C10 C9 119.5(2) . . ? C22 C10 N2 121.9(2) . . ? C9 C10 N2 118.4(2) . . ? C23 C11 C12 119.4(2) . . ? C23 C11 N2 122.7(2) . . ? C12 C11 N2 117.6(2) . . ? C13 C12 C11 122.0(3) . . ? C13 C12 H5 120.4(18) . . ? C11 C12 H5 117.5(18) . . ? C12 C13 C14 117.6(3) . . ? C12 C13 C36 119.7(3) . . ? C14 C13 C36 122.6(3) . . ? C13 C14 C15 121.6(3) . . ? C13 C14 H6 120.7(17) . . ? C15 C14 H6 117.7(17) . . ? C23 C15 C14 119.4(3) . . ? C23 C15 N3 122.5(2) . . ? C14 C15 N3 117.9(2) . . ? C17 C16 C24 119.9(3) . . ? C17 C16 N3 119.4(3) . . ? C24 C16 N3 120.5(2) . . ? C18 C17 C16 121.5(3) . . ? C18 C17 H7 121.8(17) . . ? C16 C17 H7 116.7(17) . . ? C17 C18 C19 117.9(3) . . ? C17 C18 C41 121.8(3) . . ? C19 C18 C41 120.2(3) . . ? C20 C19 C18 121.9(3) . . ? C20 C19 H8 118.9(17) . . ? C18 C19 H8 119.2(17) . . ? C19 C20 C24 119.3(3) . . ? C19 C20 N4 119.4(3) . . ? C24 C20 N4 121.1(3) . . ? O1 C21 C1 120.2(2) . . ? O1 C21 C5 120.1(2) . . ? C1 C21 C5 119.7(3) . . ? O2 C22 C10 119.8(2) . . ? O2 C22 C6 120.4(2) . . ? C10 C22 C6 119.8(2) . . ? O3 C23 C15 119.7(2) . . ? O3 C23 C11 120.4(2) . . ? C15 C23 C11 119.8(2) . . ? O4 C24 C16 120.2(2) . . ? O4 C24 C20 120.2(2) . . ? C16 C24 C20 119.5(2) . . ? O1 C25 H9 109.5 . . ? O1 C25 H10 109.5 . . ? H9 C25 H10 109.5 . . ? O1 C25 H11 109.5 . . ? H9 C25 H11 109.5 . . ? H10 C25 H11 109.5 . . ? C29 C26 C3 112.4(3) . . ? C29 C26 C27 108.3(3) . . ? C3 C26 C27 109.3(3) . . ? C29 C26 C28 107.8(3) . . ? C3 C26 C28 109.7(3) . . ? C27 C26 C28 109.1(3) . . ? C26 C27 H12 109.5 . . ? C26 C27 H13 109.5 . . ? H12 C27 H13 109.5 . . ? C26 C27 H14 109.5 . . ? H12 C27 H14 109.5 . . ? H13 C27 H14 109.5 . . ? C26 C28 H15 109.5 . . ? C26 C28 H16 109.5 . . ? H15 C28 H16 109.5 . . ? C26 C28 H17 109.5 . . ? H15 C28 H17 109.5 . . ? H16 C28 H17 109.5 . . ? C26 C29 H18 109.5 . . ? C26 C29 H19 109.5 . . ? H18 C29 H19 109.5 . . ? C26 C29 H20 109.5 . . ? H18 C29 H20 109.5 . . ? H19 C29 H20 109.5 . . ? O2 C30 H21 109.5 . . ? O2 C30 H22 109.5 . . ? H21 C30 H22 109.5 . . ? O2 C30 H23 109.5 . . ? H21 C30 H23 109.5 . . ? H22 C30 H23 109.5 . . ? C33 C31 C32 107.2(3) . . ? C33 C31 C34 110.0(3) . . ? C32 C31 C34 107.8(3) . . ? C33 C31 C8 109.6(3) . . ? C32 C31 C8 112.5(3) . . ? C34 C31 C8 109.7(3) . . ? C31 C32 H24 109.5 . . ? C31 C32 H25 109.5 . . ? H24 C32 H25 109.5 . . ? C31 C32 H26 109.5 . . ? H24 C32 H26 109.5 . . ? H25 C32 H26 109.5 . . ? C31 C33 H27 109.5 . . ? C31 C33 H28 109.5 . . ? H27 C33 H28 109.5 . . ? C31 C33 H29 109.5 . . ? H27 C33 H29 109.5 . . ? H28 C33 H29 109.5 . . ? C31 C34 H30 109.5 . . ? C31 C34 H31 109.5 . . ? H30 C34 H31 109.5 . . ? C31 C34 H32 109.5 . . ? H30 C34 H32 109.5 . . ? H31 C34 H32 109.5 . . ? O3 C35 H33 109.5 . . ? O3 C35 H34 109.5 . . ? H33 C35 H34 109.5 . . ? O3 C35 H35 109.5 . . ? H33 C35 H35 109.5 . . ? H34 C35 H35 109.5 . . ? C39 C36 C37 109.7(3) . . ? C39 C36 C13 112.9(2) . . ? C37 C36 C13 108.9(2) . . ? C39 C36 C38 107.1(3) . . ? C37 C36 C38 108.5(3) . . ? C13 C36 C38 109.6(2) . . ? C36 C37 H36 109.5 . . ? C36 C37 H37 109.5 . . ? H36 C37 H37 109.5 . . ? C36 C37 H38 109.5 . . ? H36 C37 H38 109.5 . . ? H37 C37 H38 109.5 . . ? C36 C38 H39 109.5 . . ? C36 C38 H40 109.5 . . ? H39 C38 H40 109.5 . . ? C36 C38 H41 109.5 . . ? H39 C38 H41 109.5 . . ? H40 C38 H41 109.5 . . ? C36 C39 H42 109.5 . . ? C36 C39 H43 109.5 . . ? H42 C39 H43 109.5 . . ? C36 C39 H44 109.5 . . ? H42 C39 H44 109.5 . . ? H43 C39 H44 109.5 . . ? O4 C40 H45 109.5 . . ? O4 C40 H46 109.5 . . ? H45 C40 H46 109.5 . . ? O4 C40 H47 109.5 . . ? H45 C40 H47 109.5 . . ? H46 C40 H47 109.5 . . ? C44 C41 C45 125.6(6) . . ? C44 C41 C18 118.8(6) . . ? C45 C41 C18 115.1(3) . . ? C44 C41 C46 41.9(6) . . ? C45 C41 C46 111.8(4) . . ? C18 C41 C46 109.4(3) . . ? C44 C41 C42 110.7(8) . . ? C45 C41 C42 58.3(5) . . ? C18 C41 C42 106.8(4) . . ? C46 C41 C42 142.8(5) . . ? C44 C41 C47 60.7(7) . . ? C45 C41 C47 109.9(5) . . ? C18 C41 C47 107.4(3) . . ? C46 C41 C47 102.6(4) . . ? C42 C41 C47 57.5(5) . . ? C44 C41 C43 110.3(8) . . ? C45 C41 C43 44.6(5) . . ? C18 C41 C43 106.2(5) . . ? C46 C41 C43 75.4(5) . . ? C42 C41 C43 102.9(6) . . ? C47 C41 C43 144.9(5) . . ? C41 C42 H48 109.5 . . ? C41 C42 H49 109.5 . . ? H48 C42 H49 109.5 . . ? C41 C42 H50 109.5 . . ? H48 C42 H50 109.5 . . ? H49 C42 H50 109.5 . . ? C41 C43 H51 109.5 . . ? C41 C43 H52 109.5 . . ? H51 C43 H52 109.5 . . ? C41 C43 H53 109.5 . . ? H51 C43 H53 109.5 . . ? H52 C43 H53 109.5 . . ? C41 C44 H54 109.5 . . ? C41 C44 H55 109.5 . . ? H54 C44 H55 109.5 . . ? C41 C44 H56 109.5 . . ? H54 C44 H56 109.5 . . ? H55 C44 H56 109.5 . . ? C41 C45 H57 109.5 . . ? C41 C45 H58 109.5 . . ? C41 C45 H59 109.5 . . ? C41 C46 H60 109.5 . . ? C41 C46 H61 109.5 . . ? C41 C46 H62 109.5 . . ? C41 C47 H63 109.5 . . ? C41 C47 H64 109.5 . . ? C41 C47 H65 109.5 . . ? C21 O1 C25 113.2(2) . . ? C22 O2 C30 113.0(2) . . ? C23 O3 C35 116.4(2) . . ? C24 O4 C40 113.5(2) . . ? C10 N2 C11 129.1(2) . . ? C10 N2 H67 116(2) . . ? C11 N2 H67 114(2) . . ? C20 N4 C1 127.5(2) . . ? C20 N4 H69 117(2) . . ? C1 N4 H69 116(2) . . ? C5 N1 C6 128.0(2) . . ? C5 N1 H66 114(2) . . ? C6 N1 H66 114(2) . . ? C16 N3 C15 128.6(2) . . ? C16 N3 H68 116.6(19) . . ? C15 N3 H68 113.8(19) . . ? 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 C21 C1 C2 C3 -0.6(4) . . . . ? N4 C1 C2 C3 -176.3(3) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? C1 C2 C3 C26 -179.4(3) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C26 C3 C4 C5 179.1(3) . . . . ? C3 C4 C5 C21 1.3(4) . . . . ? C3 C4 C5 N1 174.8(3) . . . . ? C22 C6 C7 C8 -0.3(4) . . . . ? N1 C6 C7 C8 175.7(3) . . . . ? C6 C7 C8 C9 1.7(4) . . . . ? C6 C7 C8 C31 178.7(3) . . . . ? C7 C8 C9 C10 -1.1(4) . . . . ? C31 C8 C9 C10 -178.0(3) . . . . ? C8 C9 C10 C22 -1.0(4) . . . . ? C8 C9 C10 N2 -177.0(3) . . . . ? C23 C11 C12 C13 -1.4(4) . . . . ? N2 C11 C12 C13 -176.0(3) . . . . ? C11 C12 C13 C14 -1.7(4) . . . . ? C11 C12 C13 C36 -178.8(3) . . . . ? C12 C13 C14 C15 2.7(4) . . . . ? C36 C13 C14 C15 179.7(3) . . . . ? C13 C14 C15 C23 -0.7(4) . . . . ? C13 C14 C15 N3 174.5(3) . . . . ? C24 C16 C17 C18 -0.2(4) . . . . ? N3 C16 C17 C18 174.7(3) . . . . ? C16 C17 C18 C19 2.2(4) . . . . ? C16 C17 C18 C41 179.3(3) . . . . ? C17 C18 C19 C20 -2.2(5) . . . . ? C41 C18 C19 C20 -179.3(3) . . . . ? C18 C19 C20 C24 0.2(4) . . . . ? C18 C19 C20 N4 -174.5(3) . . . . ? C2 C1 C21 O1 -178.5(3) . . . . ? N4 C1 C21 O1 -2.9(4) . . . . ? C2 C1 C21 C5 3.0(4) . . . . ? N4 C1 C21 C5 178.6(3) . . . . ? C4 C5 C21 O1 178.2(3) . . . . ? N1 C5 C21 O1 4.7(4) . . . . ? C4 C5 C21 C1 -3.4(4) . . . . ? N1 C5 C21 C1 -176.8(3) . . . . ? C9 C10 C22 O2 -177.9(2) . . . . ? N2 C10 C22 O2 -2.0(4) . . . . ? C9 C10 C22 C6 2.4(4) . . . . ? N2 C10 C22 C6 178.2(2) . . . . ? C7 C6 C22 O2 178.5(2) . . . . ? N1 C6 C22 O2 2.7(4) . . . . ? C7 C6 C22 C10 -1.7(4) . . . . ? N1 C6 C22 C10 -177.6(3) . . . . ? C14 C15 C23 O3 -178.9(2) . . . . ? N3 C15 C23 O3 6.1(4) . . . . ? C14 C15 C23 C11 -2.5(4) . . . . ? N3 C15 C23 C11 -177.4(3) . . . . ? C12 C11 C23 O3 179.9(3) . . . . ? N2 C11 C23 O3 -5.7(4) . . . . ? C12 C11 C23 C15 3.5(4) . . . . ? N2 C11 C23 C15 177.8(3) . . . . ? C17 C16 C24 O4 179.0(2) . . . . ? N3 C16 C24 O4 4.2(4) . . . . ? C17 C16 C24 C20 -1.8(4) . . . . ? N3 C16 C24 C20 -176.7(2) . . . . ? C19 C20 C24 O4 -179.0(3) . . . . ? N4 C20 C24 O4 -4.4(4) . . . . ? C19 C20 C24 C16 1.8(4) . . . . ? N4 C20 C24 C16 176.4(3) . . . . ? C2 C3 C26 C29 -8.2(4) . . . . ? C4 C3 C26 C29 173.9(3) . . . . ? C2 C3 C26 C27 112.1(3) . . . . ? C4 C3 C26 C27 -65.8(4) . . . . ? C2 C3 C26 C28 -128.3(3) . . . . ? C4 C3 C26 C28 53.9(4) . . . . ? C9 C8 C31 C33 111.6(4) . . . . ? C7 C8 C31 C33 -65.3(4) . . . . ? C9 C8 C31 C32 -7.6(4) . . . . ? C7 C8 C31 C32 175.5(3) . . . . ? C9 C8 C31 C34 -127.6(3) . . . . ? C7 C8 C31 C34 55.6(4) . . . . ? C12 C13 C36 C39 -166.2(3) . . . . ? C14 C13 C36 C39 16.8(4) . . . . ? C12 C13 C36 C37 71.7(4) . . . . ? C14 C13 C36 C37 -105.2(3) . . . . ? C12 C13 C36 C38 -46.9(4) . . . . ? C14 C13 C36 C38 136.2(3) . . . . ? C17 C18 C41 C44 179.1(8) . . . . ? C19 C18 C41 C44 -4.0(9) . . . . ? C17 C18 C41 C45 7.3(6) . . . . ? C19 C18 C41 C45 -175.8(5) . . . . ? C17 C18 C41 C46 134.1(4) . . . . ? C19 C18 C41 C46 -49.0(5) . . . . ? C17 C18 C41 C42 -55.0(6) . . . . ? C19 C18 C41 C42 122.0(5) . . . . ? C17 C18 C41 C47 -115.4(4) . . . . ? C19 C18 C41 C47 61.6(4) . . . . ? C17 C18 C41 C43 54.2(6) . . . . ? C19 C18 C41 C43 -128.8(5) . . . . ? C1 C21 O1 C25 90.2(3) . . . . ? C5 C21 O1 C25 -91.3(3) . . . . ? C10 C22 O2 C30 94.4(3) . . . . ? C6 C22 O2 C30 -85.8(3) . . . . ? C15 C23 O3 C35 -104.8(3) . . . . ? C11 C23 O3 C35 78.7(3) . . . . ? C16 C24 O4 C40 -92.2(3) . . . . ? C20 C24 O4 C40 88.7(3) . . . . ? C22 C10 N2 C11 37.7(4) . . . . ? C9 C10 N2 C11 -146.4(3) . . . . ? C23 C11 N2 C10 33.5(5) . . . . ? C12 C11 N2 C10 -152.0(3) . . . . ? C19 C20 N4 C1 -145.6(3) . . . . ? C24 C20 N4 C1 39.8(4) . . . . ? C21 C1 N4 C20 39.1(4) . . . . ? C2 C1 N4 C20 -145.3(3) . . . . ? C4 C5 N1 C6 141.6(3) . . . . ? C21 C5 N1 C6 -44.9(5) . . . . ? C22 C6 N1 C5 -32.9(5) . . . . ? C7 C6 N1 C5 151.2(3) . . . . ? C17 C16 N3 C15 141.6(3) . . . . ? C24 C16 N3 C15 -43.6(4) . . . . ? C23 C15 N3 C16 -30.6(5) . . . . ? C14 C15 N3 C16 154.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.482 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.052 _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. \nRele ; _chemical_absolute_configuration ? data_cmpd_2a _database_code_depnum_ccdc_archive 'CCDC 841916' #TrackingRef '6923_web_deposit_cif_file_0_HirohitoTsue_ #1314588024.tsue110829.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44.4 H60 N4 O4.8' _chemical_formula_weight 726.56 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 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 12.836(8) _cell_length_b 16.215(9) _cell_length_c 21.460(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.817(10) _cell_angle_gamma 90.00 _cell_volume 4372(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133 _cell_measurement_reflns_used 7690 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1571.2 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.6533 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34429 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.47 _reflns_number_total 9903 _reflns_number_gt 4346 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_cell_refinement ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_data_reduction ; Rigaku CrystalClear-SM Expert 2.0 r4 ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.2000P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9903 _refine_ls_number_parameters 554 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2393 _refine_ls_R_factor_gt 0.1433 _refine_ls_wR_factor_ref 0.4355 _refine_ls_wR_factor_gt 0.3704 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.221 _refine_ls_shift/su_max 0.003 _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 0.5351(5) 0.3582(3) 0.1608(3) 0.0500(14) Uani 1 1 d . . . C2 C 0.6021(5) 0.2905(3) 0.1790(3) 0.0558(15) Uani 1 1 d . . . H1 H 0.6768 0.2990 0.1909 0.067 Uiso 1 1 calc R . . C3 C 0.5614(4) 0.2106(3) 0.1800(3) 0.0483(14) Uani 1 1 d . . . C4 C 0.4493(5) 0.2011(3) 0.1667(3) 0.0490(14) Uani 1 1 d . . . H2 H 0.4199 0.1478 0.1698 0.059 Uiso 1 1 calc R . . C5 C 0.3813(4) 0.2678(3) 0.1490(3) 0.0445(12) Uani 1 1 d . . . C6 C 0.1877(4) 0.3017(3) 0.1437(3) 0.0435(13) Uani 1 1 d . . . C7 C 0.0911(4) 0.3019(3) 0.0996(2) 0.0424(12) Uani 1 1 d . . . H3 H 0.0862 0.2730 0.0606 0.051 Uiso 1 1 calc R . . C8 C 0.0008(4) 0.3435(3) 0.1111(2) 0.0397(12) Uani 1 1 d . . . C9 C 0.0113(4) 0.3890(3) 0.1676(2) 0.0429(12) Uani 1 1 d . . . H4 H -0.0481 0.4188 0.1760 0.051 Uiso 1 1 calc R . . C10 C 0.1074(4) 0.3911(3) 0.2115(2) 0.0386(12) Uani 1 1 d . . . C11 C 0.1961(4) 0.4813(3) 0.3054(2) 0.0413(12) Uani 1 1 d . . . C12 C 0.2007(4) 0.4871(3) 0.3702(3) 0.0451(13) Uani 1 1 d . . . H5 H 0.1504 0.4569 0.3880 0.054 Uiso 1 1 calc R . . C13 C 0.2755(4) 0.5349(3) 0.4106(3) 0.0458(13) Uani 1 1 d . . . C14 C 0.3526(4) 0.5748(3) 0.3829(3) 0.0486(14) Uani 1 1 d . . . H6 H 0.4082 0.6049 0.4093 0.058 Uiso 1 1 calc R . . C15 C 0.3490(4) 0.5709(3) 0.3172(3) 0.0486(14) Uani 1 1 d . . . C16 C 0.4634(4) 0.6054(3) 0.2374(3) 0.0500(14) Uani 1 1 d . . . C17 C 0.4796(4) 0.6724(3) 0.1995(3) 0.0577(16) Uani 1 1 d . . . H7 H 0.4571 0.7257 0.2096 0.069 Uiso 1 1 calc R . . C18 C 0.5284(4) 0.6634(3) 0.1467(3) 0.0558(16) Uani 1 1 d . A . C19 C 0.5571(4) 0.5837(3) 0.1325(3) 0.0571(16) Uani 1 1 d . . . H8 H 0.5887 0.5756 0.0966 0.069 Uiso 1 1 calc R . . C20 C 0.5413(4) 0.5153(3) 0.1689(3) 0.0471(13) Uani 1 1 d . . . C21 C 0.4245(4) 0.3473(3) 0.1445(3) 0.0460(13) Uani 1 1 d . . . C22 C 0.1949(4) 0.3466(3) 0.2000(3) 0.0438(13) Uani 1 1 d . . . C23 C 0.2684(4) 0.5246(3) 0.2770(3) 0.0481(13) Uani 1 1 d . . . C24 C 0.4973(4) 0.5266(3) 0.2223(3) 0.0491(14) Uani 1 1 d . . . C25 C 0.3357(7) 0.4273(5) 0.0571(3) 0.083(2) Uani 1 1 d . . . H9 H 0.3000 0.3789 0.0350 0.125 Uiso 1 1 calc R . . H10 H 0.4034 0.4363 0.0438 0.125 Uiso 1 1 calc R . . H11 H 0.2901 0.4759 0.0465 0.125 Uiso 1 1 calc R . . C26 C 0.6345(5) 0.1357(3) 0.2002(4) 0.0644(18) Uani 1 1 d . . . C27 C 0.6186(7) 0.1045(4) 0.2645(4) 0.088(2) Uani 1 1 d . . . H12 H 0.5429 0.0936 0.2623 0.132 Uiso 1 1 calc R . . H13 H 0.6435 0.1462 0.2971 0.132 Uiso 1 1 calc R . . H14 H 0.6592 0.0535 0.2754 0.132 Uiso 1 1 calc R . . C28 C 0.6040(6) 0.0655(4) 0.1500(4) 0.086(2) Uani 1 1 d . . . H15 H 0.5297 0.0495 0.1476 0.129 Uiso 1 1 calc R . . H16 H 0.6503 0.0178 0.1627 0.129 Uiso 1 1 calc R . . H17 H 0.6129 0.0853 0.1083 0.129 Uiso 1 1 calc R . . C29 C 0.7525(5) 0.1556(4) 0.2068(5) 0.102(3) Uani 1 1 d . . . H18 H 0.7949 0.1062 0.2209 0.153 Uiso 1 1 calc R . . H19 H 0.7725 0.1998 0.2381 0.153 Uiso 1 1 calc R . . H20 H 0.7658 0.1735 0.1655 0.153 Uiso 1 1 calc R . . C30 C 0.2998(6) 0.2808(5) 0.2889(3) 0.080(2) Uani 1 1 d . . . H21 H 0.2888 0.2288 0.2652 0.120 Uiso 1 1 calc R . . H22 H 0.2464 0.2862 0.3154 0.120 Uiso 1 1 calc R . . H23 H 0.3711 0.2814 0.3161 0.120 Uiso 1 1 calc R . . C31 C -0.1034(5) 0.3424(3) 0.0598(3) 0.0524(14) Uani 1 1 d . . . C32 C -0.0867(7) 0.3917(6) 0.0009(4) 0.110(3) Uani 1 1 d . . . H24 H -0.0412 0.3600 -0.0218 0.165 Uiso 1 1 calc R . . H25 H -0.0527 0.4445 0.0147 0.165 Uiso 1 1 calc R . . H26 H -0.1558 0.4017 -0.0274 0.165 Uiso 1 1 calc R . . C33 C -0.1975(6) 0.3826(4) 0.0824(4) 0.076(2) Uani 1 1 d . . . H27 H -0.1862 0.4423 0.0863 0.114 Uiso 1 1 calc R . . H28 H -0.2030 0.3597 0.1239 0.114 Uiso 1 1 calc R . . H29 H -0.2635 0.3714 0.0515 0.114 Uiso 1 1 calc R . . C34 C -0.1334(7) 0.2521(5) 0.0403(5) 0.106(3) Uani 1 1 d . . . H30 H -0.1372 0.2197 0.0784 0.159 Uiso 1 1 calc R . . H31 H -0.0793 0.2285 0.0193 0.159 Uiso 1 1 calc R . . H32 H -0.2028 0.2511 0.0110 0.159 Uiso 1 1 calc R . . C35 C 0.1866(7) 0.5671(4) 0.1736(3) 0.084(2) Uani 1 1 d . . . H33 H 0.2149 0.6216 0.1661 0.125 Uiso 1 1 calc R . . H34 H 0.1256 0.5737 0.1942 0.125 Uiso 1 1 calc R . . H35 H 0.1638 0.5385 0.1328 0.125 Uiso 1 1 calc R . . C36 C 0.2723(6) 0.5410(4) 0.4831(3) 0.074(2) Uani 1 1 d . . . C37 C 0.3127(9) 0.4545(5) 0.5122(4) 0.111(3) Uani 1 1 d . . . H36 H 0.2708 0.4105 0.4876 0.167 Uiso 1 1 calc R . . H37 H 0.3046 0.4517 0.5566 0.167 Uiso 1 1 calc R . . H38 H 0.3879 0.4476 0.5105 0.167 Uiso 1 1 calc R . . C38 C 0.1617(7) 0.5587(5) 0.4929(3) 0.083(2) Uani 1 1 d . . . H39 H 0.1347 0.6089 0.4698 0.125 Uiso 1 1 calc R . . H40 H 0.1635 0.5663 0.5384 0.125 Uiso 1 1 calc R . . H41 H 0.1149 0.5123 0.4769 0.125 Uiso 1 1 calc R . . C39 C 0.3445(8) 0.6091(5) 0.5165(3) 0.102(3) Uani 1 1 d . . . H42 H 0.3328 0.6161 0.5599 0.152 Uiso 1 1 calc R . . H43 H 0.3282 0.6609 0.4930 0.152 Uiso 1 1 calc R . . H44 H 0.4190 0.5942 0.5182 0.152 Uiso 1 1 calc R . . C40 C 0.5711(7) 0.4413(4) 0.3077(3) 0.088(3) Uani 1 1 d . . . H45 H 0.5848 0.4873 0.3379 0.132 Uiso 1 1 calc R . . H46 H 0.6336 0.4326 0.2888 0.132 Uiso 1 1 calc R . . H47 H 0.5569 0.3912 0.3301 0.132 Uiso 1 1 calc R . . C41 C 0.5452(5) 0.7382(4) 0.1052(4) 0.071(2) Uani 1 1 d D . . C42 C 0.4319(15) 0.7765(12) 0.0844(9) 0.090(5) Uani 0.45 1 d P A 2 H48 H 0.3873 0.7399 0.0537 0.134 Uiso 0.45 1 calc PR A 2 H49 H 0.4375 0.8304 0.0646 0.134 Uiso 0.45 1 calc PR A 2 H50 H 0.3999 0.7834 0.1218 0.134 Uiso 0.45 1 calc PR A 2 C43 C 0.6038(16) 0.8053(8) 0.1548(9) 0.094(7) Uani 0.45 1 d PD A 2 H51 H 0.5965 0.8599 0.1348 0.141 Uiso 0.45 1 calc PR A 2 H52 H 0.6795 0.7913 0.1676 0.141 Uiso 0.45 1 calc PR A 2 H53 H 0.5715 0.8059 0.1924 0.141 Uiso 0.45 1 calc PR A 2 C44 C 0.599(3) 0.7181(11) 0.0558(16) 0.145(14) Uani 0.45 1 d P A 2 H54 H 0.6129 0.7686 0.0339 0.217 Uiso 0.45 1 calc PR A 2 H55 H 0.5541 0.6811 0.0254 0.217 Uiso 0.45 1 calc PR A 2 H56 H 0.6661 0.6906 0.0738 0.217 Uiso 0.45 1 calc PR A 2 C45 C 0.5129(13) 0.8196(7) 0.1247(8) 0.075(4) Uani 0.55 1 d P A 1 H57 H 0.5199 0.8605 0.0922 0.113 Uiso 0.55 1 calc PR A 1 H58 H 0.5586 0.8353 0.1653 0.113 Uiso 0.55 1 calc PR A 1 H59 H 0.4386 0.8174 0.1295 0.113 Uiso 0.55 1 calc PR A 1 C46 C 0.6604(10) 0.7364(7) 0.0928(7) 0.060(3) Uani 0.55 1 d PD A 1 H60 H 0.6701 0.7827 0.0652 0.090 Uiso 0.55 1 calc PR A 1 H61 H 0.6720 0.6844 0.0720 0.090 Uiso 0.55 1 calc PR A 1 H62 H 0.7115 0.7410 0.1333 0.090 Uiso 0.55 1 calc PR A 1 C47 C 0.4786(12) 0.7228(7) 0.0350(6) 0.080(4) Uani 0.55 1 d PD A 1 H63 H 0.4923 0.6668 0.0213 0.120 Uiso 0.55 1 calc PR A 1 H64 H 0.5001 0.7629 0.0058 0.120 Uiso 0.55 1 calc PR A 1 H65 H 0.4025 0.7291 0.0345 0.120 Uiso 0.55 1 calc PR A 1 C48 C 0.591(6) 0.150(3) 0.408(2) 0.37(6) Uani 0.40 1 d PD . . O4 O 0.4820(3) 0.4598(2) 0.2592(2) 0.0554(10) Uani 1 1 d . . . O1 O 0.3557(3) 0.4134(2) 0.12556(18) 0.0517(10) Uani 1 1 d . . . N2 N 0.1112(4) 0.4350(3) 0.2685(2) 0.0498(12) Uani 1 1 d . . . H67 H 0.054(4) 0.434(3) 0.282(2) 0.034(13) Uiso 1 1 d . . . N1 N 0.2722(4) 0.2528(2) 0.1311(2) 0.0508(12) Uani 1 1 d . . . H66 H 0.2537 0.2074 0.1093 0.061 Uiso 1 1 calc R . . O2 O 0.2896(3) 0.3480(2) 0.24516(18) 0.0500(10) Uani 1 1 d . . . O3 O 0.2667(3) 0.5204(3) 0.21349(18) 0.0606(11) Uani 1 1 d . . . N4 N 0.5801(4) 0.4381(3) 0.1549(3) 0.0575(14) Uani 1 1 d . . . H69 H 0.640(4) 0.436(3) 0.138(2) 0.036(13) Uiso 1 1 d . . . N3 N 0.4233(4) 0.6187(3) 0.2931(3) 0.0590(14) Uani 1 1 d . . . H68 H 0.430(4) 0.670(3) 0.307(2) 0.048(15) Uiso 1 1 d . . . O5 O 0.643(2) 0.0907(18) 0.4147(15) 0.213(11) Uani 0.40 1 d PD . . O6 O 0.554(3) 0.2152(18) 0.3930(18) 0.264(16) Uani 0.40 1 d PD . . 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 0.056(3) 0.025(2) 0.075(4) -0.010(2) 0.027(3) 0.002(2) C2 0.045(3) 0.034(3) 0.088(4) 0.001(3) 0.013(3) 0.000(2) C3 0.043(3) 0.036(3) 0.069(4) -0.007(2) 0.021(3) 0.003(2) C4 0.061(4) 0.032(3) 0.059(3) -0.013(2) 0.022(3) -0.006(2) C5 0.044(3) 0.036(3) 0.054(3) -0.009(2) 0.012(3) 0.004(2) C6 0.051(3) 0.026(2) 0.055(3) -0.006(2) 0.012(3) -0.003(2) C7 0.055(3) 0.031(2) 0.042(3) -0.004(2) 0.015(3) 0.004(2) C8 0.051(3) 0.024(2) 0.044(3) -0.001(2) 0.010(2) 0.000(2) C9 0.053(3) 0.031(2) 0.049(3) -0.003(2) 0.020(3) -0.002(2) C10 0.049(3) 0.034(2) 0.035(3) -0.008(2) 0.015(2) -0.011(2) C11 0.044(3) 0.035(2) 0.047(3) -0.011(2) 0.015(2) 0.004(2) C12 0.060(3) 0.025(2) 0.053(3) -0.001(2) 0.018(3) -0.005(2) C13 0.059(3) 0.027(2) 0.048(3) 0.003(2) 0.004(3) -0.001(2) C14 0.048(3) 0.031(2) 0.061(4) 0.000(2) -0.002(3) -0.002(2) C15 0.049(3) 0.032(2) 0.068(4) -0.006(2) 0.019(3) 0.002(2) C16 0.045(3) 0.044(3) 0.066(4) -0.011(3) 0.022(3) -0.010(2) C17 0.044(3) 0.029(3) 0.102(5) -0.009(3) 0.019(3) -0.010(2) C18 0.044(3) 0.037(3) 0.091(5) -0.003(3) 0.025(3) -0.002(2) C19 0.041(3) 0.049(3) 0.088(4) -0.009(3) 0.030(3) -0.006(2) C20 0.037(3) 0.035(3) 0.073(4) -0.010(3) 0.020(3) 0.000(2) C21 0.045(3) 0.035(3) 0.058(3) -0.011(2) 0.012(3) 0.003(2) C22 0.045(3) 0.026(2) 0.058(3) 0.004(2) 0.004(3) -0.007(2) C23 0.045(3) 0.049(3) 0.053(3) -0.014(3) 0.017(3) -0.012(2) C24 0.046(3) 0.030(2) 0.075(4) -0.008(3) 0.021(3) -0.012(2) C25 0.100(6) 0.083(5) 0.061(4) -0.005(4) 0.005(4) 0.030(4) C26 0.044(3) 0.044(3) 0.104(5) -0.008(3) 0.012(3) 0.003(3) C27 0.096(6) 0.056(4) 0.105(6) 0.019(4) 0.006(5) 0.021(4) C28 0.083(5) 0.053(4) 0.123(7) -0.019(4) 0.025(5) 0.020(3) C29 0.048(4) 0.051(4) 0.207(10) 0.008(5) 0.022(5) 0.014(3) C30 0.058(4) 0.092(5) 0.079(5) 0.026(4) -0.013(4) 0.003(4) C31 0.055(3) 0.054(3) 0.048(3) -0.005(3) 0.012(3) 0.010(3) C32 0.103(6) 0.156(8) 0.065(5) 0.048(5) 0.003(5) 0.030(6) C33 0.075(5) 0.074(4) 0.076(5) -0.013(4) 0.009(4) 0.022(4) C34 0.079(6) 0.085(6) 0.137(8) -0.038(5) -0.023(5) 0.007(4) C35 0.135(7) 0.063(4) 0.048(4) -0.003(3) 0.007(4) -0.038(4) C36 0.106(6) 0.051(3) 0.049(4) 0.022(3) -0.018(4) -0.032(4) C37 0.166(9) 0.071(5) 0.079(5) 0.035(4) -0.015(6) -0.015(5) C38 0.100(6) 0.104(6) 0.051(4) -0.016(4) 0.026(4) -0.021(5) C39 0.160(8) 0.091(5) 0.039(4) 0.002(3) -0.014(4) -0.043(6) C40 0.135(7) 0.058(4) 0.064(4) 0.014(3) 0.005(5) -0.037(4) C41 0.066(4) 0.042(3) 0.107(6) 0.010(3) 0.021(4) -0.001(3) C42 0.097(14) 0.082(11) 0.101(14) -0.010(10) 0.048(11) 0.010(11) C43 0.137(17) 0.029(7) 0.146(18) -0.014(9) 0.096(16) -0.004(9) C44 0.21(3) 0.047(9) 0.24(3) -0.062(16) 0.18(3) -0.033(15) C45 0.089(10) 0.042(6) 0.110(11) 0.027(7) 0.055(10) 0.009(7) C46 0.075(9) 0.035(6) 0.080(9) 0.008(6) 0.038(7) -0.002(6) C47 0.081(9) 0.048(6) 0.104(11) 0.027(7) 0.002(8) 0.007(6) C48 0.75(15) 0.21(5) 0.13(3) -0.02(3) 0.00(5) 0.27(8) O4 0.065(3) 0.0383(19) 0.068(3) -0.0041(18) 0.026(2) -0.0081(18) O1 0.064(3) 0.0336(18) 0.059(2) -0.0043(16) 0.018(2) 0.0092(17) N2 0.043(3) 0.056(3) 0.054(3) -0.016(2) 0.019(2) -0.019(2) N1 0.054(3) 0.028(2) 0.068(3) -0.019(2) 0.008(2) 0.0044(19) O2 0.050(2) 0.0435(19) 0.056(2) -0.0088(17) 0.0084(19) -0.0041(17) O3 0.069(3) 0.077(3) 0.042(2) -0.018(2) 0.026(2) -0.024(2) N4 0.059(3) 0.034(2) 0.091(4) -0.006(2) 0.044(3) -0.002(2) N3 0.060(3) 0.033(2) 0.091(4) -0.025(2) 0.033(3) -0.019(2) O5 0.25(3) 0.18(2) 0.23(3) -0.01(2) 0.09(3) 0.01(2) O6 0.28(4) 0.23(3) 0.30(4) -0.03(3) 0.10(3) -0.06(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 C1 C2 1.400(7) . ? C1 C21 1.402(7) . ? C1 N4 1.434(6) . ? C2 C3 1.398(7) . ? C2 H1 0.9500 . ? C3 C4 1.417(7) . ? C3 C26 1.542(8) . ? C4 C5 1.393(7) . ? C4 H2 0.9500 . ? C5 N1 1.396(7) . ? C5 C21 1.414(7) . ? C6 C7 1.397(7) . ? C6 C22 1.398(7) . ? C6 N1 1.413(6) . ? C7 C8 1.406(7) . ? C7 H3 0.9500 . ? C8 C9 1.401(7) . ? C8 C31 1.548(8) . ? C9 C10 1.391(7) . ? C9 H4 0.9500 . ? C10 C22 1.398(7) . ? C10 N2 1.408(6) . ? C11 C12 1.384(7) . ? C11 C23 1.399(7) . ? C11 N2 1.423(7) . ? C12 C13 1.390(7) . ? C12 H5 0.9500 . ? C13 C14 1.412(8) . ? C13 C36 1.568(9) . ? C14 C15 1.403(8) . ? C14 H6 0.9500 . ? C15 N3 1.407(7) . ? C15 C23 1.419(7) . ? C16 C17 1.398(8) . ? C16 C24 1.409(7) . ? C16 N3 1.410(7) . ? C17 C18 1.410(8) . ? C17 H7 0.9500 . ? C18 C19 1.394(8) . ? C18 C41 1.545(9) . ? C19 C20 1.395(8) . ? C19 H8 0.9500 . ? C20 C24 1.388(7) . ? C20 N4 1.404(6) . ? C21 O1 1.395(6) . ? C22 O2 1.391(6) . ? C23 O3 1.360(6) . ? C24 O4 1.381(6) . ? C25 O1 1.456(8) . ? C25 H9 0.9800 . ? C25 H10 0.9800 . ? C25 H11 0.9800 . ? C26 C27 1.522(10) . ? C26 C29 1.527(9) . ? C26 C28 1.560(9) . ? C27 H12 0.9800 . ? C27 H13 0.9800 . ? C27 H14 0.9800 . ? C28 H15 0.9800 . ? C28 H16 0.9800 . ? C28 H17 0.9800 . ? C29 H18 0.9800 . ? C29 H19 0.9800 . ? C29 H20 0.9800 . ? C30 O2 1.426(7) . ? C30 H21 0.9800 . ? C30 H22 0.9800 . ? C30 H23 0.9800 . ? C31 C33 1.536(8) . ? C31 C32 1.547(9) . ? C31 C34 1.549(9) . ? C32 H24 0.9800 . ? C32 H25 0.9800 . ? C32 H26 0.9800 . ? C33 H27 0.9800 . ? C33 H28 0.9800 . ? C33 H29 0.9800 . ? C34 H30 0.9800 . ? C34 H31 0.9800 . ? C34 H32 0.9800 . ? C35 O3 1.417(8) . ? C35 H33 0.9800 . ? C35 H34 0.9800 . ? C35 H35 0.9800 . ? C36 C38 1.505(11) . ? C36 C39 1.524(9) . ? C36 C37 1.579(9) . ? C37 H36 0.9800 . ? C37 H37 0.9800 . ? C37 H38 0.9800 . ? C38 H39 0.9800 . ? C38 H40 0.9800 . ? C38 H41 0.9800 . ? C39 H42 0.9800 . ? C39 H43 0.9800 . ? C39 H44 0.9800 . ? C40 O4 1.412(8) . ? C40 H45 0.9800 . ? C40 H46 0.9800 . ? C40 H47 0.9800 . ? C41 C44 1.42(2) . ? C41 C45 1.470(13) . ? C41 C46 1.556(12) . ? C41 C42 1.560(19) . ? C41 C47 1.594(12) . ? C41 C43 1.599(14) . ? C42 H48 0.9800 . ? C42 H49 0.9800 . ? C42 H50 0.9800 . ? C43 H51 0.9800 . ? C43 H52 0.9800 . ? C43 H53 0.9800 . ? C44 H54 0.9800 . ? C44 H55 0.9800 . ? C44 H56 0.9800 . ? C45 H57 0.9800 . ? C45 H58 0.9800 . ? C45 H59 0.9800 . ? C46 H60 0.9800 . ? C46 H61 0.9800 . ? C46 H62 0.9800 . ? C47 H63 0.9800 . ? C47 H64 0.9800 . ? C47 H65 0.9800 . ? C48 O5 1.156(18) . ? C48 O6 1.182(17) . ? N2 H67 0.84(5) . ? N1 H66 0.8800 . ? N4 H69 0.91(5) . ? N3 H68 0.89(6) . ? 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 C21 120.2(5) . . ? C2 C1 N4 119.8(5) . . ? C21 C1 N4 119.9(5) . . ? C3 C2 C1 121.3(5) . . ? C3 C2 H1 119.3 . . ? C1 C2 H1 119.3 . . ? C2 C3 C4 117.7(5) . . ? C2 C3 C26 121.8(5) . . ? C4 C3 C26 120.3(5) . . ? C5 C4 C3 121.6(5) . . ? C5 C4 H2 119.2 . . ? C3 C4 H2 119.2 . . ? C4 C5 N1 118.6(4) . . ? C4 C5 C21 119.6(5) . . ? N1 C5 C21 121.6(5) . . ? C7 C6 C22 118.5(5) . . ? C7 C6 N1 118.8(4) . . ? C22 C6 N1 122.7(5) . . ? C6 C7 C8 122.1(5) . . ? C6 C7 H3 118.9 . . ? C8 C7 H3 118.9 . . ? C9 C8 C7 117.9(5) . . ? C9 C8 C31 122.5(4) . . ? C7 C8 C31 119.5(4) . . ? C10 C9 C8 120.9(5) . . ? C10 C9 H4 119.6 . . ? C8 C9 H4 119.6 . . ? C9 C10 C22 120.1(4) . . ? C9 C10 N2 118.0(5) . . ? C22 C10 N2 121.8(5) . . ? C12 C11 C23 120.6(5) . . ? C12 C11 N2 117.7(5) . . ? C23 C11 N2 121.6(5) . . ? C11 C12 C13 123.1(5) . . ? C11 C12 H5 118.4 . . ? C13 C12 H5 118.4 . . ? C12 C13 C14 116.6(5) . . ? C12 C13 C36 119.9(5) . . ? C14 C13 C36 123.5(5) . . ? C15 C14 C13 121.4(5) . . ? C15 C14 H6 119.3 . . ? C13 C14 H6 119.3 . . ? C14 C15 N3 117.4(5) . . ? C14 C15 C23 120.3(5) . . ? N3 C15 C23 122.2(5) . . ? C17 C16 C24 118.7(5) . . ? C17 C16 N3 119.8(5) . . ? C24 C16 N3 121.2(5) . . ? C16 C17 C18 122.0(5) . . ? C16 C17 H7 119.0 . . ? C18 C17 H7 119.0 . . ? C19 C18 C17 116.9(5) . . ? C19 C18 C41 121.9(6) . . ? C17 C18 C41 121.2(5) . . ? C18 C19 C20 122.6(6) . . ? C18 C19 H8 118.7 . . ? C20 C19 H8 118.7 . . ? C24 C20 C19 119.2(5) . . ? C24 C20 N4 121.1(5) . . ? C19 C20 N4 119.3(5) . . ? O1 C21 C1 121.6(4) . . ? O1 C21 C5 119.1(5) . . ? C1 C21 C5 119.3(5) . . ? O2 C22 C10 119.2(5) . . ? O2 C22 C6 120.3(5) . . ? C10 C22 C6 120.5(5) . . ? O3 C23 C11 122.4(5) . . ? O3 C23 C15 119.8(5) . . ? C11 C23 C15 117.8(5) . . ? O4 C24 C20 120.0(4) . . ? O4 C24 C16 119.5(5) . . ? C20 C24 C16 120.4(5) . . ? O1 C25 H9 109.5 . . ? O1 C25 H10 109.5 . . ? H9 C25 H10 109.5 . . ? O1 C25 H11 109.5 . . ? H9 C25 H11 109.5 . . ? H10 C25 H11 109.5 . . ? C27 C26 C29 107.5(7) . . ? C27 C26 C3 109.3(5) . . ? C29 C26 C3 113.2(5) . . ? C27 C26 C28 108.8(6) . . ? C29 C26 C28 108.8(6) . . ? C3 C26 C28 109.2(5) . . ? C26 C27 H12 109.5 . . ? C26 C27 H13 109.5 . . ? H12 C27 H13 109.5 . . ? C26 C27 H14 109.5 . . ? H12 C27 H14 109.5 . . ? H13 C27 H14 109.5 . . ? C26 C28 H15 109.5 . . ? C26 C28 H16 109.5 . . ? H15 C28 H16 109.5 . . ? C26 C28 H17 109.5 . . ? H15 C28 H17 109.5 . . ? H16 C28 H17 109.5 . . ? C26 C29 H18 109.5 . . ? C26 C29 H19 109.5 . . ? H18 C29 H19 109.5 . . ? C26 C29 H20 109.5 . . ? H18 C29 H20 109.5 . . ? H19 C29 H20 109.5 . . ? O2 C30 H21 109.5 . . ? O2 C30 H22 109.5 . . ? H21 C30 H22 109.5 . . ? O2 C30 H23 109.5 . . ? H21 C30 H23 109.5 . . ? H22 C30 H23 109.5 . . ? C33 C31 C32 106.8(6) . . ? C33 C31 C8 113.0(5) . . ? C32 C31 C8 109.3(5) . . ? C33 C31 C34 108.5(6) . . ? C32 C31 C34 109.6(7) . . ? C8 C31 C34 109.5(5) . . ? C31 C32 H24 109.5 . . ? C31 C32 H25 109.5 . . ? H24 C32 H25 109.5 . . ? C31 C32 H26 109.5 . . ? H24 C32 H26 109.5 . . ? H25 C32 H26 109.5 . . ? C31 C33 H27 109.5 . . ? C31 C33 H28 109.5 . . ? H27 C33 H28 109.5 . . ? C31 C33 H29 109.5 . . ? H27 C33 H29 109.5 . . ? H28 C33 H29 109.5 . . ? C31 C34 H30 109.5 . . ? C31 C34 H31 109.5 . . ? H30 C34 H31 109.5 . . ? C31 C34 H32 109.5 . . ? H30 C34 H32 109.5 . . ? H31 C34 H32 109.5 . . ? O3 C35 H33 109.5 . . ? O3 C35 H34 109.5 . . ? H33 C35 H34 109.5 . . ? O3 C35 H35 109.5 . . ? H33 C35 H35 109.5 . . ? H34 C35 H35 109.5 . . ? C38 C36 C39 107.2(7) . . ? C38 C36 C13 111.5(5) . . ? C39 C36 C13 112.0(5) . . ? C38 C36 C37 110.9(7) . . ? C39 C36 C37 109.8(6) . . ? C13 C36 C37 105.3(6) . . ? C36 C37 H36 109.5 . . ? C36 C37 H37 109.5 . . ? H36 C37 H37 109.5 . . ? C36 C37 H38 109.5 . . ? H36 C37 H38 109.5 . . ? H37 C37 H38 109.5 . . ? C36 C38 H39 109.5 . . ? C36 C38 H40 109.5 . . ? H39 C38 H40 109.5 . . ? C36 C38 H41 109.5 . . ? H39 C38 H41 109.5 . . ? H40 C38 H41 109.5 . . ? C36 C39 H42 109.5 . . ? C36 C39 H43 109.5 . . ? H42 C39 H43 109.5 . . ? C36 C39 H44 109.5 . . ? H42 C39 H44 109.5 . . ? H43 C39 H44 109.5 . . ? O4 C40 H45 109.5 . . ? O4 C40 H46 109.5 . . ? H45 C40 H46 109.5 . . ? O4 C40 H47 109.5 . . ? H45 C40 H47 109.5 . . ? H46 C40 H47 109.5 . . ? C44 C41 C45 128.9(11) . . ? C44 C41 C18 113.4(10) . . ? C45 C41 C18 117.5(7) . . ? C44 C41 C46 40.8(14) . . ? C45 C41 C46 113.5(9) . . ? C18 C41 C46 109.5(6) . . ? C44 C41 C42 116.4(18) . . ? C45 C41 C42 54.7(9) . . ? C18 C41 C42 104.3(8) . . ? C46 C41 C42 145.2(10) . . ? C44 C41 C47 60.2(16) . . ? C45 C41 C47 106.4(9) . . ? C18 C41 C47 108.1(6) . . ? C46 C41 C47 100.3(9) . . ? C42 C41 C47 60.3(9) . . ? C44 C41 C43 114.9(14) . . ? C45 C41 C43 47.2(8) . . ? C18 C41 C43 104.7(8) . . ? C46 C41 C43 78.0(9) . . ? C42 C41 C43 101.7(11) . . ? C47 C41 C43 145.6(9) . . ? C41 C42 H48 109.5 . . ? C41 C42 H49 109.5 . . ? H48 C42 H49 109.5 . . ? C41 C42 H50 109.5 . . ? H48 C42 H50 109.5 . . ? H49 C42 H50 109.5 . . ? C41 C43 H51 109.5 . . ? C41 C43 H52 109.5 . . ? H51 C43 H52 109.5 . . ? C41 C43 H53 109.5 . . ? H51 C43 H53 109.5 . . ? H52 C43 H53 109.5 . . ? C41 C44 H54 109.5 . . ? C41 C44 H55 109.5 . . ? H54 C44 H55 109.5 . . ? C41 C44 H56 109.5 . . ? H54 C44 H56 109.5 . . ? H55 C44 H56 109.5 . . ? C41 C45 H57 109.5 . . ? C41 C45 H58 109.5 . . ? C41 C45 H59 109.5 . . ? C41 C46 H60 109.5 . . ? C41 C46 H61 109.5 . . ? C41 C46 H62 109.5 . . ? C41 C47 H63 109.5 . . ? C41 C47 H64 109.5 . . ? C41 C47 H65 109.5 . . ? O5 C48 O6 165(8) . . ? C24 O4 C40 113.6(5) . . ? C21 O1 C25 112.6(4) . . ? C10 N2 C11 129.6(5) . . ? C10 N2 H67 115(3) . . ? C11 N2 H67 116(3) . . ? C5 N1 C6 128.1(4) . . ? C5 N1 H66 116.0 . . ? C6 N1 H66 116.0 . . ? C22 O2 C30 113.3(4) . . ? C23 O3 C35 116.0(5) . . ? C20 N4 C1 128.3(5) . . ? C20 N4 H69 119(3) . . ? C1 N4 H69 112(3) . . ? C15 N3 C16 128.3(5) . . ? C15 N3 H68 115(3) . . ? C16 N3 H68 114(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 C21 C1 C2 C3 1.6(9) . . . . ? N4 C1 C2 C3 -174.5(5) . . . . ? C1 C2 C3 C4 -4.7(9) . . . . ? C1 C2 C3 C26 -179.8(6) . . . . ? C2 C3 C4 C5 4.1(9) . . . . ? C26 C3 C4 C5 179.3(5) . . . . ? C3 C4 C5 N1 174.4(5) . . . . ? C3 C4 C5 C21 -0.3(8) . . . . ? C22 C6 C7 C8 -2.0(7) . . . . ? N1 C6 C7 C8 174.7(4) . . . . ? C6 C7 C8 C9 3.0(7) . . . . ? C6 C7 C8 C31 179.1(5) . . . . ? C7 C8 C9 C10 -1.5(7) . . . . ? C31 C8 C9 C10 -177.5(4) . . . . ? C8 C9 C10 C22 -0.8(7) . . . . ? C8 C9 C10 N2 -177.3(4) . . . . ? C23 C11 C12 C13 -0.1(8) . . . . ? N2 C11 C12 C13 -175.7(5) . . . . ? C11 C12 C13 C14 -3.6(7) . . . . ? C11 C12 C13 C36 177.5(5) . . . . ? C12 C13 C14 C15 4.4(7) . . . . ? C36 C13 C14 C15 -176.7(5) . . . . ? C13 C14 C15 N3 174.3(5) . . . . ? C13 C14 C15 C23 -1.6(8) . . . . ? C24 C16 C17 C18 0.2(9) . . . . ? N3 C16 C17 C18 174.2(5) . . . . ? C16 C17 C18 C19 1.9(9) . . . . ? C16 C17 C18 C41 179.8(6) . . . . ? C17 C18 C19 C20 -1.3(9) . . . . ? C41 C18 C19 C20 -179.2(6) . . . . ? C18 C19 C20 C24 -1.4(9) . . . . ? C18 C19 C20 N4 -174.8(5) . . . . ? C2 C1 C21 O1 -179.3(5) . . . . ? N4 C1 C21 O1 -3.2(8) . . . . ? C2 C1 C21 C5 2.3(9) . . . . ? N4 C1 C21 C5 178.4(5) . . . . ? C4 C5 C21 O1 178.7(5) . . . . ? N1 C5 C21 O1 4.1(8) . . . . ? C4 C5 C21 C1 -2.9(8) . . . . ? N1 C5 C21 C1 -177.5(5) . . . . ? C9 C10 C22 O2 -178.6(4) . . . . ? N2 C10 C22 O2 -2.3(7) . . . . ? C9 C10 C22 C6 1.9(7) . . . . ? N2 C10 C22 C6 178.2(4) . . . . ? C7 C6 C22 O2 180.0(4) . . . . ? N1 C6 C22 O2 3.4(7) . . . . ? C7 C6 C22 C10 -0.5(7) . . . . ? N1 C6 C22 C10 -177.1(4) . . . . ? C12 C11 C23 O3 179.7(5) . . . . ? N2 C11 C23 O3 -4.8(8) . . . . ? C12 C11 C23 C15 3.0(8) . . . . ? N2 C11 C23 C15 178.5(5) . . . . ? C14 C15 C23 O3 -179.0(5) . . . . ? N3 C15 C23 O3 5.3(8) . . . . ? C14 C15 C23 C11 -2.2(8) . . . . ? N3 C15 C23 C11 -177.9(5) . . . . ? C19 C20 C24 O4 -179.4(5) . . . . ? N4 C20 C24 O4 -6.1(8) . . . . ? C19 C20 C24 C16 3.7(8) . . . . ? N4 C20 C24 C16 176.9(5) . . . . ? C17 C16 C24 O4 180.0(5) . . . . ? N3 C16 C24 O4 6.1(8) . . . . ? C17 C16 C24 C20 -3.1(8) . . . . ? N3 C16 C24 C20 -176.9(5) . . . . ? C2 C3 C26 C27 109.5(7) . . . . ? C4 C3 C26 C27 -65.5(7) . . . . ? C2 C3 C26 C29 -10.2(10) . . . . ? C4 C3 C26 C29 174.7(6) . . . . ? C2 C3 C26 C28 -131.6(6) . . . . ? C4 C3 C26 C28 53.4(8) . . . . ? C9 C8 C31 C33 -10.2(7) . . . . ? C7 C8 C31 C33 173.8(5) . . . . ? C9 C8 C31 C32 108.5(6) . . . . ? C7 C8 C31 C32 -67.4(7) . . . . ? C9 C8 C31 C34 -131.4(6) . . . . ? C7 C8 C31 C34 52.7(7) . . . . ? C12 C13 C36 C38 -47.9(7) . . . . ? C14 C13 C36 C38 133.3(6) . . . . ? C12 C13 C36 C39 -168.1(6) . . . . ? C14 C13 C36 C39 13.1(9) . . . . ? C12 C13 C36 C37 72.5(8) . . . . ? C14 C13 C36 C37 -106.3(6) . . . . ? C19 C18 C41 C44 -4.4(19) . . . . ? C17 C18 C41 C44 177.8(17) . . . . ? C19 C18 C41 C45 -179.5(9) . . . . ? C17 C18 C41 C45 2.7(12) . . . . ? C19 C18 C41 C46 -48.2(10) . . . . ? C17 C18 C41 C46 134.1(8) . . . . ? C19 C18 C41 C42 123.1(9) . . . . ? C17 C18 C41 C42 -54.7(10) . . . . ? C19 C18 C41 C47 60.2(9) . . . . ? C17 C18 C41 C47 -117.6(8) . . . . ? C19 C18 C41 C43 -130.4(9) . . . . ? C17 C18 C41 C43 51.8(10) . . . . ? C20 C24 O4 C40 88.2(7) . . . . ? C16 C24 O4 C40 -94.8(7) . . . . ? C1 C21 O1 C25 89.3(7) . . . . ? C5 C21 O1 C25 -92.3(7) . . . . ? C9 C10 N2 C11 -145.6(5) . . . . ? C22 C10 N2 C11 37.9(8) . . . . ? C12 C11 N2 C10 -151.3(5) . . . . ? C23 C11 N2 C10 33.1(8) . . . . ? C4 C5 N1 C6 142.9(5) . . . . ? C21 C5 N1 C6 -42.4(8) . . . . ? C7 C6 N1 C5 148.9(5) . . . . ? C22 C6 N1 C5 -34.6(8) . . . . ? C10 C22 O2 C30 93.8(6) . . . . ? C6 C22 O2 C30 -86.6(6) . . . . ? C11 C23 O3 C35 77.3(7) . . . . ? C15 C23 O3 C35 -106.0(6) . . . . ? C24 C20 N4 C1 40.3(9) . . . . ? C19 C20 N4 C1 -146.5(6) . . . . ? C2 C1 N4 C20 -144.9(6) . . . . ? C21 C1 N4 C20 39.0(9) . . . . ? C14 C15 N3 C16 154.8(6) . . . . ? C23 C15 N3 C16 -29.4(9) . . . . ? C17 C16 N3 C15 140.6(6) . . . . ? C24 C16 N3 C15 -45.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.591 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.087 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. \nRele ; _chemical_absolute_configuration ?