# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email brian.skelton@uwa.edu.au _publ_contact_author_name 'Brian W. Skelton' loop_ _publ_author_name D.DAlessioa 'Sara Muzzioli' 'Brian W. Skelton' 'Stefano Stagni' 'Massimiliano Massi' 'Mark I. Ogden' data_modd17eub4 _database_code_depnum_ccdc_archive 'CCDC 851653' #TrackingRef 'web_deposit_cif_file_0_BrianSkelton_1320063279.modd17eub4.cif' _audit_creation_date 2011-08-10T15:12:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C48 H61 Eu N8 O6' _chemical_formula_moiety 'C48 H61 Eu N8 O6' _chemical_formula_weight 998.01 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/m 1' _symmetry_space_group_name_Hall '-c 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 20.852(3) _cell_length_b 12.9596(12) _cell_length_c 24.4175(19) _cell_angle_alpha 90 _cell_angle_beta 103.649(11) _cell_angle_gamma 90 _cell_volume 6412.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21150 _cell_measurement_theta_min 2.977 _cell_measurement_theta_max 31.7563 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.1334 -1 -1 0 0.2008 0 -1 0 0.2307 9 -2 -1 0.297 3 1 -5 0.1066 3 2 0 0.2415 -4 3 1 0.1822 0 0 1 0.0731 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.019 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 0.821 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 -0.0202701 _diffrn_orient_matrix_ub_12 0.0165858 _diffrn_orient_matrix_ub_13 -0.0264016 _diffrn_orient_matrix_ub_21 0.0267924 _diffrn_orient_matrix_ub_22 -0.0082818 _diffrn_orient_matrix_ub_23 -0.0127097 _diffrn_orient_matrix_ub_31 -0.0109435 _diffrn_orient_matrix_ub_32 -0.0512792 _diffrn_orient_matrix_ub_33 -0.0065435 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_unetI/netI 0.032 _diffrn_reflns_number 31105 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 7685 _reflns_number_gt 7033 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. The molecule is situated on a crystallographic mirror plane. As a result, the tetrazole group, the two coordinated water molecules, and two of the tert-butyl groups are disordered over two sets of sites with occupancies constrained to 0.5. The geometries and displacement parameters of the tert-butyl grpups were restrained to realistic values. Despite many attempts, the residual electron density could not be modelled as a possible nitrate anion or as any of the solvents used. This electron density was effectively removed by use of the program Squeeze. Water molecule/hydroxyl and the possible hydrogen atoms on the tetrazole groups were not located. Refinement in a space group of lower symmetry did not improve the model. ; _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^)+(0.0657P)^2^+112.0143P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7685 _refine_ls_number_parameters 388 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.2109 _refine_ls_wR_factor_gt 0.2084 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.915 _refine_diff_density_min -1.516 _refine_diff_density_rms 0.151 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Eu1 Eu 0.46149(3) 0.5 0.359547(17) 0.03746(17) Uani 1 2 d S . . O11 O 0.5266(4) 0.5 0.3029(3) 0.0430(16) Uani 1 2 d S C . C11 C 0.5644(6) 0.5 0.2660(4) 0.042(2) Uani 1 2 d S . . C12 C 0.5841(4) 0.4065(6) 0.2453(3) 0.0432(15) Uani 1 1 d . C . C13 C 0.6204(4) 0.4085(6) 0.2046(3) 0.0436(16) Uani 1 1 d . . . H13 H 0.6342 0.3449 0.1918 0.052 Uiso 1 1 calc R C . C14 C 0.6376(5) 0.5 0.1819(4) 0.051(3) Uani 1 2 d S . . C141 C 0.6759(8) 0.5 0.1354(6) 0.081(3) Uani 1 2 d SDU . . C142 C 0.6320(10) 0.4550(15) 0.0833(8) 0.097(5) Uani 0.5 1 d PDU A -1 H14A H 0.6514 0.4672 0.0511 0.145 Uiso 0.5 1 calc PR A -1 H14B H 0.5884 0.4877 0.0764 0.145 Uiso 0.5 1 calc PR A -1 H14C H 0.6274 0.3806 0.0885 0.145 Uiso 0.5 1 calc PR A -1 C143 C 0.7401(10) 0.4464(16) 0.1546(10) 0.111(6) Uani 0.5 1 d PDU A -1 H14D H 0.7691 0.4875 0.184 0.167 Uiso 0.5 1 calc PR A -1 H14E H 0.7607 0.438 0.1227 0.167 Uiso 0.5 1 calc PR A -1 H14F H 0.733 0.3785 0.1698 0.167 Uiso 0.5 1 calc PR A -1 C144 C 0.6915(10) 0.6108(11) 0.1193(8) 0.076(4) Uani 0.5 1 d PDU A -1 H14G H 0.724 0.642 0.1506 0.114 Uiso 0.5 1 calc PR A -1 H14H H 0.651 0.6521 0.1114 0.114 Uiso 0.5 1 calc PR A -1 H14I H 0.7095 0.6088 0.0857 0.114 Uiso 0.5 1 calc PR A -1 O21 O 0.4507(3) 0.3164(3) 0.31914(17) 0.0413(11) Uani 1 1 d . C . C20 C 0.4595(4) 0.2234(5) 0.3520(3) 0.0474(18) Uani 1 1 d . . . H20A H 0.5059 0.1995 0.3595 0.057 Uiso 0.5 1 calc PR B 1 H20B H 0.4304 0.1679 0.3323 0.057 Uiso 0.5 1 calc PR B 1 H20C H 0.4768 0.167 0.3322 0.057 Uiso 0.5 1 d PR B 2 H20D H 0.4172 0.201 0.3599 0.057 Uiso 0.5 1 d PR B 2 N211 N 0.4360(6) 0.3492(8) 0.4217(4) 0.038(2) Uani 0.5 1 d P C 1 N212 N 0.4218(6) 0.3413(9) 0.4725(4) 0.043(3) Uani 0.5 1 d P C 1 N213 N 0.4157(9) 0.2452(12) 0.4840(6) 0.053(4) Uani 0.5 1 d P C 1 N214 N 0.4305(7) 0.1844(10) 0.4433(5) 0.052(3) Uani 0.5 1 d P C 1 C215 C 0.4416(8) 0.2520(10) 0.4051(5) 0.043(3) Uani 0.5 1 d P C 1 N221 N 0.5212(7) 0.3486(8) 0.4226(4) 0.042(3) Uani 0.5 1 d P C 2 N222 N 0.5640(6) 0.3424(10) 0.4743(5) 0.046(3) Uani 0.5 1 d P C 2 N223 N 0.5753(9) 0.2461(11) 0.4878(6) 0.053(4) Uani 0.5 1 d P C 2 N224 N 0.5419(7) 0.1845(9) 0.4447(5) 0.052(3) Uani 0.5 1 d P C 2 C225 C 0.5087(8) 0.2513(10) 0.4063(5) 0.044(3) Uani 0.5 1 d P C 2 C21 C 0.4331(4) 0.3000(4) 0.2598(2) 0.0390(15) Uani 1 1 d . . . C22 C 0.3676(4) 0.2942(5) 0.2314(3) 0.0426(16) Uani 1 1 d . C . C23 C 0.3525(4) 0.2819(5) 0.1724(3) 0.0455(17) Uani 1 1 d . . . H23 H 0.3077 0.277 0.1523 0.055 Uiso 1 1 calc R C . C24 C 0.4020(4) 0.2767(5) 0.1431(3) 0.0441(16) Uani 1 1 d . C . C241 C 0.3830(5) 0.2644(7) 0.0781(4) 0.0642(19) Uani 1 1 d DU . . C242 C 0.3707(6) 0.1519(7) 0.0639(4) 0.083(3) Uani 1 1 d DU C -1 H24A H 0.3361 0.1261 0.0814 0.125 Uiso 1 1 calc R C -1 H24B H 0.4114 0.1128 0.0781 0.125 Uiso 1 1 calc R C -1 H24C H 0.3566 0.1438 0.0229 0.125 Uiso 1 1 calc R C -1 C243 C 0.3216(5) 0.3254(10) 0.0512(4) 0.092(3) Uani 1 1 d DU C -1 H24D H 0.3139 0.3215 0.01 0.138 Uiso 1 1 calc R C -1 H24E H 0.3276 0.3977 0.0631 0.138 Uiso 1 1 calc R C -1 H24F H 0.2835 0.2965 0.0629 0.138 Uiso 1 1 calc R C -1 C244 C 0.4381(5) 0.3016(9) 0.0518(4) 0.084(3) Uani 1 1 d DU C -1 H24G H 0.4756 0.2543 0.0619 0.127 Uiso 1 1 calc R C -1 H24H H 0.4519 0.3709 0.0659 0.127 Uiso 1 1 calc R C -1 H24I H 0.4221 0.3038 0.0107 0.127 Uiso 1 1 calc R C -1 C25 C 0.4678(4) 0.2823(5) 0.1741(3) 0.0447(17) Uani 1 1 d . . . H25 H 0.502 0.2781 0.1545 0.054 Uiso 1 1 calc R C . C26 C 0.4847(4) 0.2938(5) 0.2324(3) 0.0387(15) Uani 1 1 d . C . C2 C 0.5575(4) 0.3076(5) 0.2631(3) 0.0453(17) Uani 1 1 d . . . H2A H 0.5616 0.3086 0.3043 0.054 Uiso 1 1 calc R C . H2B H 0.5836 0.2488 0.2543 0.054 Uiso 1 1 calc R . . O31 O 0.3638(4) 0.5 0.3005(3) 0.0458(17) Uani 1 2 d S C . C31 C 0.3062(6) 0.5 0.2624(4) 0.043(2) Uani 1 2 d S . . C34 C 0.1861(7) 0.5 0.1790(5) 0.058(3) Uani 1 2 d S . . C341 C 0.1185(6) 0.5 0.1329(5) 0.064(3) Uani 1 2 d SDU . . C342 C 0.0613(11) 0.4687(18) 0.1565(10) 0.112(9) Uani 0.5 1 d PDU D -1 H34A H 0.0664 0.4984 0.1942 0.168 Uiso 1 2 calc SR D -1 H34B H 0.0598 0.3933 0.1589 0.168 Uiso 0.5 1 calc PR D -1 H34C H 0.0202 0.4939 0.1318 0.168 Uiso 0.5 1 calc PR D -1 C343 C 0.0987(11) 0.6137(11) 0.1097(10) 0.093(7) Uani 0.5 1 d PDU D -1 H34D H 0.1348 0.6434 0.0955 0.14 Uiso 0.5 1 calc PR D -1 H34E H 0.0904 0.6568 0.1403 0.14 Uiso 0.5 1 calc PR D -1 H34F H 0.0587 0.6104 0.0791 0.14 Uiso 0.5 1 calc PR D -1 C344 C 0.1256(12) 0.4422(15) 0.0826(8) 0.100(8) Uani 0.5 1 d PDU D -1 H34G H 0.0838 0.4441 0.054 0.15 Uiso 0.5 1 calc PR D -1 H34H H 0.1373 0.3704 0.093 0.15 Uiso 0.5 1 calc PR D -1 H34I H 0.1604 0.4738 0.0673 0.15 Uiso 0.5 1 calc PR D -1 C35 C 0.2136(4) 0.4097(6) 0.2002(3) 0.0482(17) Uani 1 1 d . . . H35 H 0.1917 0.3467 0.1877 0.058 Uiso 1 1 calc R C . C36 C 0.2748(4) 0.4073(6) 0.2411(3) 0.0468(17) Uani 1 1 d . C . C3 C 0.3110(4) 0.3076(5) 0.2598(3) 0.0465(17) Uani 1 1 d . . . H3A H 0.2802 0.2488 0.2502 0.056 Uiso 1 1 calc R C . H3B H 0.3283 0.3084 0.3012 0.056 Uiso 1 1 calc R . . O1 O 0.5653(6) 0.5691(8) 0.4219(4) 0.051(3) Uani 0.5 1 d P . 1 O2 O 0.3915(5) 0.4311(8) 0.4188(4) 0.044(2) Uani 0.5 1 d P . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.0704(4) 0.0211(2) 0.0199(2) 0 0.00866(19) 0 O11 0.080(5) 0.021(3) 0.030(3) 0 0.018(3) 0 C11 0.066(7) 0.032(5) 0.031(4) 0 0.016(4) 0 C12 0.057(4) 0.039(4) 0.034(3) 0.002(3) 0.010(3) 0.006(3) C13 0.048(4) 0.048(4) 0.038(3) -0.001(3) 0.017(3) 0.003(3) C14 0.044(6) 0.071(8) 0.037(5) 0 0.007(4) 0 C141 0.099(7) 0.087(7) 0.072(6) 0 0.051(5) 0 C142 0.112(8) 0.101(8) 0.087(8) -0.006(6) 0.042(7) -0.009(6) C143 0.116(8) 0.119(9) 0.107(8) 0.011(7) 0.043(7) 0.008(7) C144 0.094(7) 0.082(8) 0.068(7) 0.005(6) 0.050(6) -0.006(6) O21 0.083(4) 0.0178(19) 0.0232(19) 0.0019(16) 0.012(2) 0.001(2) C20 0.089(6) 0.022(3) 0.029(3) 0.007(2) 0.010(3) 0.002(3) N211 0.057(7) 0.032(5) 0.028(5) -0.003(4) 0.019(5) -0.004(5) N212 0.064(8) 0.041(6) 0.023(5) -0.004(4) 0.008(5) -0.011(6) N213 0.085(11) 0.050(8) 0.023(6) -0.005(7) 0.014(7) -0.010(7) N214 0.084(10) 0.035(6) 0.035(6) 0.009(5) 0.013(6) -0.012(6) C215 0.081(10) 0.026(6) 0.019(5) 0.006(4) 0.005(6) -0.008(6) N221 0.072(8) 0.024(5) 0.027(5) 0.005(4) 0.008(5) 0.008(5) N222 0.060(8) 0.043(6) 0.031(5) -0.001(5) 0.004(5) 0.010(6) N223 0.090(11) 0.037(7) 0.029(7) 0.012(6) 0.008(8) 0.017(7) N224 0.088(10) 0.034(6) 0.035(6) 0.008(5) 0.018(6) 0.016(6) C225 0.084(11) 0.025(6) 0.028(6) 0.005(5) 0.023(6) 0.013(6) C21 0.075(5) 0.019(3) 0.022(3) 0.001(2) 0.009(3) -0.004(3) C22 0.075(5) 0.020(3) 0.032(3) -0.001(2) 0.013(3) -0.006(3) C23 0.077(5) 0.028(3) 0.030(3) -0.001(2) 0.009(3) -0.013(3) C24 0.077(5) 0.027(3) 0.027(3) -0.001(2) 0.008(3) -0.003(3) C241 0.082(4) 0.066(4) 0.045(3) 0.001(3) 0.016(3) -0.002(3) C242 0.114(6) 0.081(5) 0.053(4) -0.023(4) 0.016(4) -0.012(5) C243 0.105(6) 0.106(6) 0.058(5) 0.011(5) 0.006(4) 0.019(5) C244 0.098(6) 0.106(6) 0.051(4) 0.003(4) 0.021(4) -0.017(5) C25 0.081(5) 0.027(3) 0.028(3) -0.001(2) 0.017(3) 0.003(3) C26 0.064(4) 0.021(3) 0.029(3) -0.002(2) 0.007(3) 0.002(3) C2 0.075(5) 0.033(3) 0.028(3) 0.001(3) 0.010(3) 0.010(3) O31 0.075(5) 0.029(3) 0.029(3) 0 0.003(3) 0 C31 0.060(6) 0.041(5) 0.029(4) 0 0.011(4) 0 C34 0.071(8) 0.064(8) 0.042(6) 0 0.022(5) 0 C341 0.061(6) 0.068(7) 0.062(6) 0 0.011(5) 0 C342 0.100(11) 0.116(14) 0.115(12) 0.010(9) 0.011(8) -0.011(9) C343 0.083(10) 0.089(10) 0.098(10) -0.005(8) 0.003(8) 0.018(8) C344 0.101(11) 0.098(11) 0.096(11) -0.015(8) 0.014(8) 0.020(8) C35 0.054(4) 0.052(4) 0.043(4) -0.003(3) 0.018(3) -0.013(4) C36 0.067(5) 0.042(4) 0.034(3) 0.000(3) 0.016(3) -0.007(3) C3 0.070(5) 0.033(3) 0.036(3) 0.000(3) 0.011(3) -0.012(3) O1 0.074(7) 0.045(6) 0.033(5) -0.010(4) 0.014(5) -0.001(5) O2 0.060(6) 0.042(5) 0.029(4) 0.004(4) 0.010(4) -0.003(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Eu1 O11 2.156(7) . ? Eu1 O31 2.201(7) . ? Eu1 O2 2.453(9) . ? Eu1 O2 2.453(9) 6_565 ? Eu1 O1 2.499(11) . ? Eu1 O1 2.499(11) 6_565 ? Eu1 O21 2.565(4) . ? Eu1 O21 2.565(4) 6_565 ? Eu1 N211 2.604(10) . ? Eu1 N211 2.604(10) 6_565 ? Eu1 N221 2.619(10) 6_565 ? Eu1 N221 2.619(10) . ? O11 C11 1.329(12) . ? C11 C12 1.411(9) 6_565 ? C11 C12 1.411(8) . ? C12 C13 1.384(9) . ? C12 C2 1.501(10) . ? C13 C14 1.392(9) . ? C13 H13 0.95 . ? C14 C13 1.392(9) 6_565 ? C14 C141 1.533(16) . ? C141 C143 1.484(15) . ? C141 C143 1.484(15) 6_565 ? C141 C142 1.498(15) . ? C141 C142 1.498(15) 6_565 ? C141 C144 1.544(13) 6_565 ? C141 C144 1.544(13) . ? C142 H14A 0.98 . ? C142 H14B 0.98 . ? C142 H14C 0.98 . ? C143 H14D 0.98 . ? C143 H14E 0.98 . ? C143 H14F 0.98 . ? C144 H14G 0.98 . ? C144 H14H 0.98 . ? C144 H14I 0.98 . ? O21 C21 1.424(7) . ? O21 C20 1.436(7) . ? C20 C215 1.477(15) . ? C20 C225 1.515(16) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C20 H20C 0.99 . ? C20 H20D 0.99 . ? N211 C215 1.338(17) . ? N211 N212 1.346(14) . ? N212 N213 1.290(19) . ? N213 N214 1.359(19) . ? N214 C215 1.339(16) . ? C215 H20D 1.2845 . ? N221 C225 1.329(17) . ? N221 N222 1.366(15) . ? N222 N223 1.298(18) . ? N223 N224 1.37(2) . ? N224 C225 1.344(17) . ? C21 C22 1.381(10) . ? C21 C26 1.397(10) . ? C22 C23 1.409(9) . ? C22 C3 1.513(11) . ? C23 C24 1.389(11) . ? C23 H23 0.95 . ? C24 C25 1.403(11) . ? C24 C241 1.552(10) . ? C241 C242 1.506(11) . ? C241 C243 1.517(11) . ? C241 C244 1.520(11) . ? C242 H24A 0.98 . ? C242 H24B 0.98 . ? C242 H24C 0.98 . ? C243 H24D 0.98 . ? C243 H24E 0.98 . ? C243 H24F 0.98 . ? C244 H24G 0.98 . ? C244 H24H 0.98 . ? C244 H24I 0.98 . ? C25 C26 1.392(8) . ? C25 H25 0.95 . ? C26 C2 1.537(10) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? O31 C31 1.334(13) . ? C31 C36 1.408(9) . ? C31 C36 1.408(9) 6_565 ? C34 C35 1.352(10) 6_565 ? C34 C35 1.352(10) . ? C34 C341 1.582(18) . ? C341 C344 1.476(15) 6_565 ? C341 C344 1.476(15) . ? C341 C342 1.497(15) 6_565 ? C341 C342 1.497(15) . ? C341 C343 1.597(14) 6_565 ? C341 C343 1.597(14) . ? C342 H34A 0.98 . ? C342 H34B 0.98 . ? C342 H34C 0.98 . ? C343 H34D 0.98 . ? C343 H34E 0.98 . ? C343 H34F 0.98 . ? C344 H34G 0.98 . ? C344 H34H 0.98 . ? C344 H34I 0.98 . ? C35 C36 1.423(11) . ? C35 H35 0.95 . ? C36 C3 1.512(11) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? 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 O11 Eu1 O31 101.9(3) . . ? O11 Eu1 O2 158.6(2) . . ? O31 Eu1 O2 78.4(3) . . ? O11 Eu1 O2 158.6(2) . 6_565 ? O31 Eu1 O2 78.4(3) . 6_565 ? O11 Eu1 O1 78.8(3) . . ? O31 Eu1 O1 159.0(3) . . ? O2 Eu1 O1 108.7(3) . . ? O11 Eu1 O1 78.8(3) . 6_565 ? O31 Eu1 O1 159.0(3) . 6_565 ? O2 Eu1 O1 108.7(3) 6_565 6_565 ? O11 Eu1 O21 76.37(12) . . ? O31 Eu1 O21 76.39(13) . . ? O2 Eu1 O21 83.0(3) . . ? O2 Eu1 O21 123.6(3) 6_565 . ? O1 Eu1 O21 123.5(3) . . ? O1 Eu1 O21 83.5(3) 6_565 . ? O11 Eu1 O21 76.37(12) . 6_565 ? O31 Eu1 O21 76.39(13) . 6_565 ? O2 Eu1 O21 123.6(3) . 6_565 ? O2 Eu1 O21 83.0(3) 6_565 6_565 ? O1 Eu1 O21 83.5(3) . 6_565 ? O1 Eu1 O21 123.5(3) 6_565 6_565 ? O21 Eu1 O21 136.10(18) . 6_565 ? O11 Eu1 N211 128.3(2) . . ? O31 Eu1 N211 95.5(3) . . ? O2 Eu1 N211 72.4(3) 6_565 . ? O1 Eu1 N211 100.4(4) . . ? O1 Eu1 N211 69.1(4) 6_565 . ? O21 Eu1 N211 61.1(2) . . ? O21 Eu1 N211 155.3(3) 6_565 . ? O11 Eu1 N211 128.3(3) . 6_565 ? O31 Eu1 N211 95.5(3) . 6_565 ? O2 Eu1 N211 72.4(3) . 6_565 ? O1 Eu1 N211 69.1(4) . 6_565 ? O1 Eu1 N211 100.4(4) 6_565 6_565 ? O21 Eu1 N211 155.3(3) . 6_565 ? O21 Eu1 N211 61.1(2) 6_565 6_565 ? N211 Eu1 N211 97.2(5) . 6_565 ? O11 Eu1 N221 95.4(3) . 6_565 ? O31 Eu1 N221 128.5(3) . 6_565 ? O2 Eu1 N221 101.1(3) . 6_565 ? O2 Eu1 N221 69.3(4) 6_565 6_565 ? O1 Eu1 N221 71.8(4) 6_565 6_565 ? O21 Eu1 N221 155.1(3) . 6_565 ? O21 Eu1 N221 61.2(3) 6_565 6_565 ? N211 Eu1 N221 110.7(3) . 6_565 ? O11 Eu1 N221 95.4(3) . . ? O31 Eu1 N221 128.5(3) . . ? O2 Eu1 N221 69.3(4) . . ? O2 Eu1 N221 101.1(3) 6_565 . ? O1 Eu1 N221 71.8(4) . . ? O21 Eu1 N221 61.2(3) . . ? O21 Eu1 N221 155.1(3) 6_565 . ? N211 Eu1 N221 110.7(3) 6_565 . ? N221 Eu1 N221 97.0(5) 6_565 . ? C11 O11 Eu1 177.4(7) . . ? O11 C11 C12 120.8(5) . 6_565 ? O11 C11 C12 120.8(5) . . ? C12 C11 C12 118.4(9) 6_565 . ? C13 C12 C11 119.7(7) . . ? C13 C12 C2 121.7(6) . . ? C11 C12 C2 118.1(6) . . ? C12 C13 C14 122.5(7) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C13 C14 C13 116.9(9) 6_565 . ? C13 C14 C141 121.5(5) 6_565 . ? C13 C14 C141 121.5(5) . . ? C143 C141 C142 114.3(12) . . ? C143 C141 C142 114.3(12) 6_565 6_565 ? C143 C141 C14 110.8(13) . . ? C143 C141 C14 110.8(13) 6_565 . ? C142 C141 C14 107.9(13) . . ? C142 C141 C14 107.9(13) 6_565 . ? C143 C141 C144 106.6(12) 6_565 6_565 ? C142 C141 C144 105.7(11) 6_565 6_565 ? C14 C141 C144 111.5(8) . 6_565 ? C143 C141 C144 106.6(12) . . ? C142 C141 C144 105.7(11) . . ? C14 C141 C144 111.5(8) . . ? C141 C142 H14A 109.5 . . ? C141 C142 H14B 109.5 . . ? C141 C142 H14C 109.5 . . ? C141 C143 H14D 109.5 . . ? C141 C143 H14E 109.5 . . ? C141 C143 H14F 109.5 . . ? C141 C144 H14G 109.5 . . ? C141 C144 H14H 109.5 . . ? C141 C144 H14I 109.5 . . ? C21 O21 C20 114.3(4) . . ? C21 O21 Eu1 120.5(3) . . ? C20 O21 Eu1 125.1(3) . . ? O21 C20 C215 104.7(7) . . ? O21 C20 C225 105.0(7) . . ? O21 C20 H20A 110.8 . . ? O21 C20 H20B 110.8 . . ? C215 C20 H20B 110.8 . . ? H20A C20 H20B 108.9 . . ? O21 C20 H20C 111 . . ? C225 C20 H20C 110.8 . . ? O21 C20 H20D 110.6 . . ? C225 C20 H20D 110.6 . . ? H20C C20 H20D 108.8 . . ? C215 N211 N212 105.1(10) . . ? C215 N211 Eu1 119.1(8) . . ? N212 N211 Eu1 135.6(8) . . ? N213 N212 N211 109.2(11) . . ? N212 N213 N214 110.5(12) . . ? C215 N214 N213 103.7(12) . . ? N211 C215 N214 111.3(12) . . ? N211 C215 C20 124.1(10) . . ? N214 C215 C20 124.6(12) . . ? C225 N221 N222 105.1(11) . . ? C225 N221 Eu1 120.2(9) . . ? N222 N221 Eu1 134.7(8) . . ? N223 N222 N221 109.3(12) . . ? N222 N223 N224 109.6(12) . . ? C225 N224 N223 104.2(12) . . ? N221 C225 N224 111.7(13) . . ? N221 C225 C20 122.2(11) . . ? N224 C225 C20 126.0(12) . . ? C22 C21 C26 122.6(6) . . ? C22 C21 O21 120.5(6) . . ? C26 C21 O21 116.9(6) . . ? C21 C22 C23 118.4(7) . . ? C21 C22 C3 123.2(6) . . ? C23 C22 C3 118.2(7) . . ? C24 C23 C22 121.2(7) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 118.1(6) . . ? C23 C24 C241 119.4(7) . . ? C25 C24 C241 122.6(7) . . ? C242 C241 C243 108.9(8) . . ? C242 C241 C244 108.4(8) . . ? C243 C241 C244 107.2(8) . . ? C242 C241 C24 108.9(7) . . ? C243 C241 C24 112.0(8) . . ? C244 C241 C24 111.3(7) . . ? C241 C242 H24A 109.5 . . ? C241 C242 H24B 109.5 . . ? C241 C242 H24C 109.5 . . ? C241 C243 H24D 109.5 . . ? C241 C243 H24E 109.5 . . ? C241 C243 H24F 109.5 . . ? C241 C244 H24G 109.5 . . ? C241 C244 H24H 109.5 . . ? C241 C244 H24I 109.5 . . ? C26 C25 C24 122.5(7) . . ? C26 C25 H25 118.8 . . ? C24 C25 H25 118.8 . . ? C25 C26 C21 117.2(7) . . ? C25 C26 C2 119.6(7) . . ? C21 C26 C2 123.0(6) . . ? C12 C2 C26 110.4(6) . . ? C12 C2 H2A 109.6 . . ? C26 C2 H2A 109.6 . . ? C12 C2 H2B 109.6 . . ? C26 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C31 O31 Eu1 176.8(7) . . ? O31 C31 C36 121.4(5) . . ? O31 C31 C36 121.4(5) . 6_565 ? C36 C31 C36 117.2(10) . 6_565 ? C35 C34 C35 119.9(12) 6_565 . ? C35 C34 C341 120.0(6) 6_565 . ? C35 C34 C341 120.0(6) . . ? C344 C341 C342 115.3(13) 6_565 6_565 ? C344 C341 C342 115.3(13) . . ? C344 C341 C34 110.2(12) 6_565 . ? C344 C341 C34 110.2(12) . . ? C342 C341 C34 112.6(13) 6_565 . ? C342 C341 C34 112.6(13) . . ? C344 C341 C343 103.9(12) 6_565 6_565 ? C342 C341 C343 102.9(11) 6_565 6_565 ? C34 C341 C343 111.4(9) . 6_565 ? C344 C341 C343 103.9(12) . . ? C342 C341 C343 102.9(11) . . ? C34 C341 C343 111.4(9) . . ? C341 C342 H34A 109.5 . . ? C341 C342 H34B 109.5 . . ? C341 C342 H34C 109.5 . . ? C341 C343 H34D 109.5 . . ? C341 C343 H34E 109.5 . . ? C341 C343 H34F 109.5 . . ? C341 C344 H34G 109.5 . . ? C341 C344 H34H 109.5 . . ? C341 C344 H34I 109.5 . . ? C34 C35 C36 121.2(8) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C31 C36 C35 120.1(7) . . ? C31 C36 C3 117.5(7) . . ? C35 C36 C3 122.2(7) . . ? C36 C3 C22 110.3(6) . . ? C36 C3 H3A 109.6 . . ? C22 C3 H3A 109.6 . . ? C36 C3 H3B 109.6 . . ? C22 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.072 0.000 0.846 24 0 ' ' 2 0.337 -0.102 0.500 1848 36 ' ' 3 0.260 0.000 0.012 12 0 ' ' 4 0.740 0.000 -0.012 12 0 ' ' 5 0.928 0.000 0.154 24 0 ' ' 6 0.240 0.500 0.988 12 0 ' ' 7 0.760 0.500 0.012 12 0 ' ' 8 0.428 0.500 0.154 24 0 ' ' 9 0.572 0.500 0.846 24 0 ' ' #===END # Attachment 'web_deposit_cif_file_1_BrianSkelton_1320063279.modd17tbb.cif' data_modd17tbb _database_code_depnum_ccdc_archive 'CCDC 851654' #TrackingRef 'web_deposit_cif_file_1_BrianSkelton_1320063279.modd17tbb.cif' _audit_creation_date 2011-05-27T14:55:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C4 H14 N3 O12 S2 Tb' _chemical_formula_moiety 'C4 H14 N3 O12 S2 Tb' _chemical_formula_weight 519.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9696(2) _cell_length_b 7.9761(2) _cell_length_c 13.9627(3) _cell_angle_alpha 75.947(2) _cell_angle_beta 87.082(2) _cell_angle_gamma 66.169(2) _cell_volume 786.47(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 23875 _cell_measurement_theta_min 3.6169 _cell_measurement_theta_max 40.9912 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.0417 0 0 1 0.0187 0 -1 -1 0.1121 0 1 1 0.07 -1 -1 0 0.1008 -2 0 1 0.0664 1 1 0 0.1204 2 0 -1 0.1969 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.823 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.394 _exptl_absorpt_correction_T_max 0.768 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0219647504 _diffrn_orient_matrix_ub_12 0.0216487658 _diffrn_orient_matrix_ub_13 -0.0514070345 _diffrn_orient_matrix_ub_21 -0.0077361376 _diffrn_orient_matrix_ub_22 -0.0874917809 _diffrn_orient_matrix_ub_23 0.0061692815 _diffrn_orient_matrix_ub_31 -0.0945815579 _diffrn_orient_matrix_ub_32 0.0437769643 _diffrn_orient_matrix_ub_33 0.0085591091 _diffrn_measurement_device_type 'Oxford Diffraction Gemini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_number 35729 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 41 _diffrn_reflns_theta_full 41 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 10211 _reflns_number_gt 9149 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0203P)^2^+0.6558P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 10211 _refine_ls_number_parameters 211 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0544 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.197 _refine_diff_density_min -1.621 _refine_diff_density_rms 0.153 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Tb1 Tb 0.708994(10) 0.250109(10) 0.225613(5) 0.00934(2) Uani 1 1 d . . . O1 O 0.5995(2) 0.18116(19) 0.09169(10) 0.0184(2) Uani 1 1 d D . . H1A H 0.610(6) 0.073(3) 0.096(3) 0.063(13) Uiso 1 1 d D . . H1B H 0.546(4) 0.243(5) 0.0368(17) 0.040(9) Uiso 1 1 d D . . N2 N 1.0324(2) 0.0867(2) 0.12089(11) 0.0149(2) Uani 1 1 d . . . O21 O 0.95263(18) 0.26433(18) 0.11527(10) 0.0164(2) Uani 1 1 d . . . O22 O 0.96889(18) -0.01639(18) 0.18295(10) 0.0164(2) Uani 1 1 d . . . O23 O 1.1597(2) 0.0210(2) 0.07058(12) 0.0265(3) Uani 1 1 d . . . N3 N 0.63387(19) 0.64652(19) 0.13149(11) 0.0128(2) Uani 1 1 d . . . O31 O 0.70770(18) 0.56382(18) 0.21831(9) 0.0158(2) Uani 1 1 d . . . O32 O 0.58043(17) 0.55074(17) 0.08833(9) 0.01372(19) Uani 1 1 d . . . O33 O 0.6139(2) 0.80698(19) 0.09064(11) 0.0215(3) Uani 1 1 d . . . N4 N 0.8712(2) 0.2262(2) 0.41267(11) 0.0151(2) Uani 1 1 d . . . O41 O 0.96554(17) 0.1875(2) 0.33832(10) 0.0168(2) Uani 1 1 d . . . O42 O 0.69989(18) 0.2725(2) 0.40096(10) 0.0188(2) Uani 1 1 d . . . O43 O 0.9414(2) 0.2207(2) 0.48975(11) 0.0251(3) Uani 1 1 d . . . C51 C 0.0828(2) 0.5763(3) 0.31429(13) 0.0170(3) Uani 1 1 d . . . H51A H 0.0625 0.4604 0.3226 0.025 Uiso 1 1 calc R . . H51B H -0.0327 0.6864 0.2916 0.025 Uiso 1 1 calc R . . H51C H 0.1264 0.5806 0.3776 0.025 Uiso 1 1 calc R . . C52 C 0.1340(3) 0.5762(3) 0.12044(14) 0.0184(3) Uani 1 1 d . . . H52A H 0.2146 0.567 0.0648 0.028 Uiso 1 1 calc R . . H52B H 0.0224 0.6929 0.1024 0.028 Uiso 1 1 calc R . . H52C H 0.1007 0.4673 0.1365 0.028 Uiso 1 1 calc R . . S5 S 0.25042(5) 0.57880(5) 0.22513(3) 0.01154(6) Uani 1 1 d . . . O5 O 0.40285(16) 0.37884(18) 0.25686(10) 0.0159(2) Uani 1 1 d . . . C61 C 0.6531(3) -0.2819(3) 0.45165(17) 0.0258(4) Uani 1 1 d . . . H61A H 0.6946 -0.3677 0.4075 0.039 Uiso 1 1 calc R . . H61B H 0.5704 -0.3171 0.4986 0.039 Uiso 1 1 calc R . . H61C H 0.7597 -0.2907 0.4879 0.039 Uiso 1 1 calc R . . C62 C 0.3723(3) -0.0775(4) 0.3129(2) 0.0285(4) Uani 1 1 d . . . H62A H 0.3054 0.0396 0.263 0.043 Uiso 1 1 calc R . . H62B H 0.2854 -0.1094 0.358 0.043 Uiso 1 1 calc R . . H62C H 0.4362 -0.1801 0.2801 0.043 Uiso 1 1 calc R . . S6 S 0.53478(6) -0.04597(6) 0.38077(3) 0.01329(6) Uani 1 1 d . . . O6 O 0.67366(17) -0.01862(17) 0.30556(9) 0.0143(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tb1 0.00909(3) 0.00817(3) 0.01060(3) -0.00229(2) 0.00013(2) -0.00327(2) O1 0.0271(6) 0.0129(5) 0.0160(5) -0.0033(4) -0.0068(5) -0.0080(5) N2 0.0128(5) 0.0141(5) 0.0159(6) -0.0032(5) 0.0021(4) -0.0038(4) O21 0.0182(5) 0.0128(5) 0.0184(5) -0.0030(4) 0.0035(4) -0.0073(4) O22 0.0162(5) 0.0116(5) 0.0186(5) -0.0021(4) 0.0047(4) -0.0040(4) O23 0.0210(6) 0.0246(7) 0.0274(7) -0.0073(6) 0.0146(6) -0.0037(5) N3 0.0140(5) 0.0109(5) 0.0147(5) -0.0037(4) 0.0005(4) -0.0060(4) O31 0.0198(5) 0.0129(5) 0.0143(5) -0.0020(4) -0.0048(4) -0.0064(4) O32 0.0172(5) 0.0107(4) 0.0150(5) -0.0033(4) -0.0027(4) -0.0068(4) O33 0.0322(7) 0.0110(5) 0.0230(6) -0.0004(4) -0.0036(5) -0.0119(5) N4 0.0171(6) 0.0141(5) 0.0145(5) -0.0034(4) -0.0018(5) -0.0064(5) O41 0.0122(5) 0.0200(6) 0.0167(5) -0.0053(4) 0.0005(4) -0.0045(4) O42 0.0156(5) 0.0267(7) 0.0170(5) -0.0089(5) 0.0027(4) -0.0095(5) O43 0.0305(7) 0.0298(7) 0.0175(6) -0.0081(5) -0.0073(5) -0.0125(6) C51 0.0145(6) 0.0149(6) 0.0175(7) -0.0018(5) 0.0030(5) -0.0035(5) C52 0.0168(7) 0.0211(8) 0.0178(7) -0.0065(6) -0.0022(6) -0.0066(6) S5 0.01001(14) 0.01013(14) 0.01440(15) -0.00255(12) -0.00005(11) -0.00415(11) O5 0.0095(4) 0.0130(5) 0.0208(6) -0.0012(4) 0.0005(4) -0.0017(4) C61 0.0261(9) 0.0166(8) 0.0263(9) 0.0041(7) 0.0077(7) -0.0062(7) C62 0.0149(7) 0.0387(12) 0.0405(12) -0.0229(10) 0.0041(8) -0.0123(8) S6 0.01510(15) 0.01194(15) 0.01373(15) -0.00439(12) 0.00332(12) -0.00596(13) O6 0.0153(5) 0.0115(5) 0.0154(5) -0.0011(4) 0.0028(4) -0.0060(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Tb1 O6 2.2832(12) . ? Tb1 O5 2.2983(12) . ? Tb1 O1 2.3694(13) . ? Tb1 O21 2.4383(13) . ? Tb1 O41 2.4551(13) . ? Tb1 O22 2.4687(13) . ? Tb1 O31 2.4752(13) . ? Tb1 O42 2.4931(14) . ? Tb1 O32 2.5409(12) . ? O1 H1A 0.823(18) . ? O1 H1B 0.833(18) . ? N2 O23 1.214(2) . ? N2 O22 1.2760(19) . ? N2 O21 1.281(2) . ? N3 O33 1.2161(19) . ? N3 O31 1.2733(19) . ? N3 O32 1.2809(18) . ? N4 O43 1.222(2) . ? N4 O42 1.270(2) . ? N4 O41 1.275(2) . ? C51 S5 1.7818(18) . ? C51 H51A 0.98 . ? C51 H51B 0.98 . ? C51 H51C 0.98 . ? C52 S5 1.7794(18) . ? C52 H52A 0.98 . ? C52 H52B 0.98 . ? C52 H52C 0.98 . ? S5 O5 1.5368(13) . ? C61 S6 1.779(2) . ? C61 H61A 0.98 . ? C61 H61B 0.98 . ? C61 H61C 0.98 . ? C62 S6 1.773(2) . ? C62 H62A 0.98 . ? C62 H62B 0.98 . ? C62 H62C 0.98 . ? S6 O6 1.5300(13) . ? 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 O6 Tb1 O5 80.39(4) . . ? O6 Tb1 O1 79.82(5) . . ? O5 Tb1 O1 83.49(5) . . ? O6 Tb1 O21 125.58(4) . . ? O5 Tb1 O21 147.70(4) . . ? O1 Tb1 O21 83.13(5) . . ? O6 Tb1 O41 93.31(5) . . ? O5 Tb1 O41 125.60(5) . . ? O1 Tb1 O41 148.86(5) . . ? O21 Tb1 O41 76.32(4) . . ? O6 Tb1 O22 73.34(4) . . ? O5 Tb1 O22 147.68(5) . . ? O1 Tb1 O22 73.73(5) . . ? O21 Tb1 O22 52.27(4) . . ? O41 Tb1 O22 75.20(5) . . ? O6 Tb1 O31 152.60(5) . . ? O5 Tb1 O31 86.66(5) . . ? O1 Tb1 O31 122.76(4) . . ? O21 Tb1 O31 76.24(4) . . ? O41 Tb1 O31 74.78(4) . . ? O22 Tb1 O31 124.90(4) . . ? O6 Tb1 O42 78.37(5) . . ? O5 Tb1 O42 74.35(5) . . ? O1 Tb1 O42 151.07(5) . . ? O21 Tb1 O42 125.24(5) . . ? O41 Tb1 O42 51.64(4) . . ? O22 Tb1 O42 117.12(5) . . ? O31 Tb1 O42 74.91(5) . . ? O6 Tb1 O32 145.12(4) . . ? O5 Tb1 O32 76.85(4) . . ? O1 Tb1 O32 71.68(4) . . ? O21 Tb1 O32 71.06(4) . . ? O41 Tb1 O32 121.44(4) . . ? O22 Tb1 O32 115.69(4) . . ? O31 Tb1 O32 51.18(4) . . ? O42 Tb1 O32 119.43(4) . . ? Tb1 O1 H1A 119(3) . . ? Tb1 O1 H1B 135(3) . . ? H1A O1 H1B 106(4) . . ? O23 N2 O22 122.34(16) . . ? O23 N2 O21 122.22(15) . . ? O22 N2 O21 115.44(14) . . ? O23 N2 Tb1 175.00(13) . . ? O22 N2 Tb1 58.53(8) . . ? O21 N2 Tb1 57.18(8) . . ? N2 O21 Tb1 96.62(9) . . ? N2 O22 Tb1 95.31(9) . . ? O33 N3 O31 122.91(15) . . ? O33 N3 O32 120.97(15) . . ? O31 N3 O32 116.12(13) . . ? O33 N3 Tb1 175.93(12) . . ? O31 N3 Tb1 56.65(8) . . ? O32 N3 Tb1 59.65(8) . . ? N3 O31 Tb1 97.90(9) . . ? N3 O32 Tb1 94.56(9) . . ? O43 N4 O42 122.30(16) . . ? O43 N4 O41 121.95(16) . . ? O42 N4 O41 115.75(14) . . ? O43 N4 Tb1 177.83(13) . . ? O42 N4 Tb1 58.73(8) . . ? O41 N4 Tb1 57.03(8) . . ? N4 O41 Tb1 97.13(10) . . ? N4 O42 Tb1 95.46(10) . . ? S5 C51 H51A 109.5 . . ? S5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? S5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? S5 C52 H52A 109.5 . . ? S5 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? S5 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O5 S5 C52 104.87(8) . . ? O5 S5 C51 103.21(8) . . ? C52 S5 C51 99.43(9) . . ? S5 O5 Tb1 133.22(7) . . ? S6 C61 H61A 109.5 . . ? S6 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? S6 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? S6 C62 H62A 109.5 . . ? S6 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? S6 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? O6 S6 C62 104.73(10) . . ? O6 S6 C61 103.30(8) . . ? C62 S6 C61 99.79(12) . . ? S6 O6 Tb1 130.12(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O33 0.823(18) 2.126(19) 2.9436(19) 172(4) 1_545 O1 H1B O32 0.833(18) 2.053(19) 2.8680(18) 166(3) 2_665 #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_modd17 _database_code_depnum_ccdc_archive 'CCDC 851655' #TrackingRef '9601_web_deposit_cif_file_0_BrianSkelton_1329269562.modd17.cif' _audit_creation_date 2012-02-14T14:34:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C52 H66 N10 O4' _chemical_formula_moiety 'C48 H60 N8 O4, 2( C2 H3 N)' _chemical_formula_weight 895.15 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-c 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.526(5) _cell_length_b 11.962(2) _cell_length_c 37.255(6) _cell_angle_alpha 90 _cell_angle_beta 110.96(2) _cell_angle_gamma 90 _cell_volume 9790(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3798 _cell_measurement_theta_min 2.7609 _cell_measurement_theta_max 27.8374 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3840 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.81004 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.0171414 _diffrn_orient_matrix_ub_12 -0.0195043 _diffrn_orient_matrix_ub_13 -0.010923 _diffrn_orient_matrix_ub_21 -0.0224457 _diffrn_orient_matrix_ub_22 -0.0413871 _diffrn_orient_matrix_ub_23 -0.0084761 _diffrn_orient_matrix_ub_31 -0.015747 _diffrn_orient_matrix_ub_32 0.0378876 _diffrn_orient_matrix_ub_33 -0.0148682 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.135 _diffrn_reflns_av_unetI/netI 0.1379 _diffrn_reflns_number 71629 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 8627 _reflns_number_gt 5115 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. One tetrazolyl group is disordered over two sets of sites with occupancies constrained at 0.5 after trial refinement. ; _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^)+(0.0319P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8627 _refine_ls_number_parameters 636 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.134 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.1677 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.232 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O11 O 0.13641(10) 0.50846(16) 0.53606(5) 0.0279(6) Uani 1 1 d . B . C10 C 0.09488(17) 0.5198(3) 0.49721(8) 0.0339(9) Uani 1 1 d . . . H10A H 0.0533 0.4981 0.4954 0.041 Uiso 0.5 1 calc PR A 1 H10B H 0.1075 0.4707 0.48 0.041 Uiso 0.5 1 calc PR A 1 H10F H 0.0527 0.5008 0.4947 0.041 Uiso 0.5 1 d PR A 2 H10G H 0.1072 0.4733 0.4792 0.041 Uiso 0.5 1 d PR A 2 C111 C 0.09577(17) 0.6383(3) 0.48591(9) 0.0332(9) Uani 0.5 1 d P B 1 N112 N 0.0737(4) 0.7259(7) 0.4969(2) 0.046(2) Uani 0.5 1 d P B 1 H112 H 0.0567 0.7259 0.5144 0.055 Uiso 0.5 1 calc PR B 1 N113 N 0.0805(5) 0.8175(8) 0.4773(2) 0.0471(17) Uani 0.5 1 d P B 1 N114 N 0.1034(7) 0.7781(14) 0.4526(4) 0.044(3) Uani 0.5 1 d PU B 1 N115 N 0.1125(6) 0.6685(15) 0.4549(5) 0.049(4) Uani 0.5 1 d PU B 1 C121 C 0.09577(17) 0.6383(3) 0.48591(9) 0.0332(9) Uani 0.5 1 d P B 2 N122 N 0.1064(4) 0.7237(7) 0.5142(2) 0.037(2) Uani 0.5 1 d P B 2 H122 H 0.1137 0.7128 0.5388 0.045 Uiso 0.5 1 calc PR B 2 N123 N 0.1036(4) 0.8225(8) 0.49730(19) 0.0471(17) Uani 0.5 1 d P B 2 N124 N 0.0929(8) 0.8016(13) 0.4601(4) 0.044(3) Uani 0.5 1 d PU B 2 N125 N 0.0917(5) 0.6824(12) 0.4548(4) 0.029(3) Uani 0.5 1 d PU B 2 C11 C 0.12901(16) 0.4047(2) 0.55184(8) 0.0246(8) Uani 1 1 d . . . C12 C 0.16518(16) 0.3151(3) 0.54880(8) 0.0260(8) Uani 1 1 d . B . C13 C 0.15597(16) 0.2116(3) 0.56341(8) 0.0265(8) Uani 1 1 d . . . H13 H 0.1804 0.1498 0.562 0.032 Uiso 1 1 calc R B . C14 C 0.11202(16) 0.1963(2) 0.58004(8) 0.0250(8) Uani 1 1 d . B . C141 C 0.10188(17) 0.0803(3) 0.59388(9) 0.0329(9) Uani 1 1 d . . . C142 C 0.0817(2) -0.0018(3) 0.55955(9) 0.0516(12) Uani 1 1 d . B . H14A H 0.0449 0.0268 0.5395 0.077 Uiso 1 1 calc R . . H14B H 0.0731 -0.0751 0.5682 0.077 Uiso 1 1 calc R . . H14C H 0.1143 -0.0092 0.5491 0.077 Uiso 1 1 calc R . . C143 C 0.16194(18) 0.0362(3) 0.62311(9) 0.0446(10) Uani 1 1 d . B . H14D H 0.1933 0.0361 0.6115 0.067 Uiso 1 1 calc R . . H14E H 0.156 -0.0401 0.6306 0.067 Uiso 1 1 calc R . . H14F H 0.1749 0.0845 0.6459 0.067 Uiso 1 1 calc R . . C144 C 0.05385(18) 0.0798(3) 0.61233(10) 0.0447(10) Uani 1 1 d . B . H14G H 0.0664 0.1299 0.6346 0.067 Uiso 1 1 calc R . . H14H H 0.0492 0.0038 0.6207 0.067 Uiso 1 1 calc R . . H14I H 0.015 0.1054 0.5936 0.067 Uiso 1 1 calc R . . C15 C 0.07878(17) 0.2894(3) 0.58315(8) 0.0295(8) Uani 1 1 d . . . H15 H 0.0489 0.2808 0.5946 0.035 Uiso 1 1 calc R B . C16 C 0.08768(16) 0.3952(3) 0.57004(8) 0.0268(8) Uani 1 1 d . B . C1 C 0.05498(17) 0.4960(3) 0.57850(8) 0.0296(8) Uani 1 1 d . . . H1A H 0.054 0.5571 0.5603 0.035 Uiso 1 1 calc R B . H1B H 0.0125 0.4755 0.5747 0.035 Uiso 1 1 calc R . . O21 O 0.25927(11) 0.55532(17) 0.56391(6) 0.0301(6) Uani 1 1 d . . . H21 H 0.2232 0.5353 0.5519 0.045 Uiso 1 1 calc R . . C21 C 0.29521(16) 0.4618(3) 0.57782(8) 0.0261(8) Uani 1 1 d . . . C22 C 0.35136(16) 0.4796(3) 0.60658(8) 0.0277(8) Uani 1 1 d . . . C23 C 0.38897(17) 0.3874(3) 0.62180(8) 0.0325(9) Uani 1 1 d . . . H23 H 0.428 0.3999 0.6408 0.039 Uiso 1 1 calc R . . C24 C 0.37131(17) 0.2782(3) 0.61017(8) 0.0308(9) Uani 1 1 d . . . C241 C 0.40956(18) 0.1760(3) 0.62912(9) 0.0370(10) Uani 1 1 d . . . C242 C 0.4723(2) 0.2089(3) 0.65643(11) 0.0625(14) Uani 1 1 d . . . H24A H 0.4932 0.2522 0.6425 0.094 Uiso 1 1 calc R . . H24B H 0.4959 0.1414 0.6671 0.094 Uiso 1 1 calc R . . H24C H 0.4685 0.2543 0.6773 0.094 Uiso 1 1 calc R . . C243 C 0.3755(2) 0.1133(3) 0.65132(10) 0.0544(13) Uani 1 1 d . . . H24D H 0.3981 0.0456 0.6629 0.082 Uiso 1 1 calc R . . H24E H 0.3348 0.0926 0.6336 0.082 Uiso 1 1 calc R . . H24F H 0.3718 0.1616 0.6716 0.082 Uiso 1 1 calc R . . C244 C 0.41735(18) 0.0967(3) 0.59924(9) 0.0403(10) Uani 1 1 d . . . H24G H 0.4386 0.1354 0.5845 0.061 Uiso 1 1 calc R . . H24H H 0.3773 0.072 0.5818 0.061 Uiso 1 1 calc R . . H24I H 0.4413 0.0317 0.6122 0.061 Uiso 1 1 calc R . . C25 C 0.31499(17) 0.2641(3) 0.58097(8) 0.0290(8) Uani 1 1 d . . . H25 H 0.3022 0.1905 0.5721 0.035 Uiso 1 1 calc R . . C26 C 0.27652(16) 0.3534(3) 0.56412(8) 0.0267(8) Uani 1 1 d . B . C2 C 0.21493(16) 0.3289(3) 0.53285(8) 0.0281(8) Uani 1 1 d . . . H2A H 0.2043 0.3909 0.514 0.034 Uiso 1 1 calc R B . H2B H 0.2182 0.2597 0.5191 0.034 Uiso 1 1 calc R . . O31 O 0.26645(11) 0.73167(17) 0.62043(5) 0.0300(6) Uani 1 1 d . . . C30 C 0.29341(17) 0.8376(3) 0.61798(8) 0.0319(9) Uani 1 1 d . . . H30A H 0.3383 0.8313 0.628 0.038 Uiso 1 1 calc R . . H30B H 0.2816 0.8942 0.6334 0.038 Uiso 1 1 calc R . . C311 C 0.27108(17) 0.8712(3) 0.57678(8) 0.0310(9) Uani 1 1 d . . . N312 N 0.26194(14) 0.8017(2) 0.54754(7) 0.0349(8) Uani 1 1 d . . . H312 H 0.2662 0.7286 0.5492 0.042 Uiso 1 1 calc R . . N313 N 0.24514(16) 0.8621(2) 0.51504(7) 0.0435(9) Uani 1 1 d . . . N314 N 0.24411(16) 0.9662(2) 0.52511(8) 0.0449(9) Uani 1 1 d . . . N315 N 0.25982(15) 0.9741(2) 0.56383(7) 0.0375(8) Uani 1 1 d . . . C31 C 0.29844(17) 0.6732(2) 0.65453(8) 0.0274(8) Uani 1 1 d . . . C32 C 0.27467(17) 0.6749(3) 0.68339(8) 0.0292(9) Uani 1 1 d . B . C33 C 0.30421(16) 0.6130(3) 0.71645(8) 0.0289(8) Uani 1 1 d . . . H33 H 0.2883 0.6133 0.7366 0.035 Uiso 1 1 calc R . . C34 C 0.35636(16) 0.5507(3) 0.72100(8) 0.0272(8) Uani 1 1 d . . . C341 C 0.38925(17) 0.4821(3) 0.75769(8) 0.0317(9) Uani 1 1 d . . . C342 C 0.34722(18) 0.4592(3) 0.77991(9) 0.0436(10) Uani 1 1 d . . . H34A H 0.3099 0.423 0.7629 0.065 Uiso 1 1 calc R . . H34B H 0.3369 0.5299 0.7894 0.065 Uiso 1 1 calc R . . H34C H 0.3678 0.41 0.8017 0.065 Uiso 1 1 calc R . . C343 C 0.41100(19) 0.3700(3) 0.74776(9) 0.0450(11) Uani 1 1 d . . . H34D H 0.4417 0.3829 0.7361 0.068 Uiso 1 1 calc R . . H34E H 0.3764 0.3295 0.7296 0.068 Uiso 1 1 calc R . . H34F H 0.4289 0.3256 0.7712 0.068 Uiso 1 1 calc R . . C344 C 0.44459(18) 0.5503(3) 0.78339(9) 0.0456(11) Uani 1 1 d . . . H34G H 0.4663 0.5079 0.8068 0.068 Uiso 1 1 calc R . . H34H H 0.4305 0.6215 0.7903 0.068 Uiso 1 1 calc R . . H34I H 0.472 0.5649 0.7694 0.068 Uiso 1 1 calc R . . C35 C 0.37844(16) 0.5520(2) 0.69140(8) 0.0280(8) Uani 1 1 d . . . H35 H 0.4147 0.5119 0.6943 0.034 Uiso 1 1 calc R . . C36 C 0.34927(16) 0.6103(2) 0.65725(8) 0.0248(8) Uani 1 1 d . . . C3 C 0.37162(16) 0.5940(2) 0.62405(8) 0.0283(8) Uani 1 1 d . . . H3A H 0.3545 0.6527 0.6044 0.034 Uiso 1 1 calc R . . H3B H 0.4166 0.5993 0.6334 0.034 Uiso 1 1 calc R . . O41 O 0.14300(11) 0.67174(18) 0.59900(5) 0.0329(6) Uani 1 1 d . B . H41 H 0.1791 0.695 0.6068 0.049 Uiso 1 1 calc R . . C41 C 0.13163(16) 0.6203(3) 0.62863(8) 0.0274(8) Uani 1 1 d . . . C42 C 0.08668(16) 0.5365(3) 0.61928(8) 0.0266(8) Uani 1 1 d . B . C43 C 0.07448(16) 0.4839(3) 0.64863(8) 0.0297(8) Uani 1 1 d . . . H43 H 0.0445 0.4267 0.6423 0.036 Uiso 1 1 calc R B . C44 C 0.10409(17) 0.5107(3) 0.68711(8) 0.0288(8) Uani 1 1 d . B . C441 C 0.09142(17) 0.4508(3) 0.71958(9) 0.0343(9) Uani 1 1 d . . . C442 C 0.0359(2) 0.3741(3) 0.70452(10) 0.0551(12) Uani 1 1 d . B . H44A H -0.0001 0.4184 0.6902 0.083 Uiso 1 1 calc R . . H44B H 0.0293 0.3372 0.7262 0.083 Uiso 1 1 calc R . . H44C H 0.0428 0.3175 0.6875 0.083 Uiso 1 1 calc R . . C443 C 0.1472(2) 0.3807(4) 0.74204(12) 0.0745(15) Uani 1 1 d . B . H44D H 0.1557 0.3272 0.7247 0.112 Uiso 1 1 calc R . . H44E H 0.1393 0.3401 0.7626 0.112 Uiso 1 1 calc R . . H44F H 0.1825 0.4299 0.7532 0.112 Uiso 1 1 calc R . . C444 C 0.0799(2) 0.5357(3) 0.74638(10) 0.0559(12) Uani 1 1 d . B . H44G H 0.116 0.5827 0.7576 0.084 Uiso 1 1 calc R . . H44H H 0.0711 0.4966 0.7669 0.084 Uiso 1 1 calc R . . H44I H 0.0451 0.5826 0.7319 0.084 Uiso 1 1 calc R . . C45 C 0.14792(17) 0.5946(3) 0.69502(9) 0.0298(9) Uani 1 1 d . . . H45 H 0.1689 0.6148 0.7211 0.036 Uiso 1 1 calc R B . C46 C 0.16234(16) 0.6498(3) 0.66690(8) 0.0274(8) Uani 1 1 d . B . C4 C 0.21528(16) 0.7330(3) 0.67881(9) 0.0294(8) Uani 1 1 d . . . H4A H 0.2074 0.7923 0.6591 0.035 Uiso 1 1 calc R B . H4B H 0.2184 0.7687 0.7034 0.035 Uiso 1 1 calc R . . N101 N 0.25670(17) 0.2143(3) 0.70954(9) 0.0604(11) Uani 1 1 d . . . C101 C 0.24835(19) 0.2786(3) 0.68565(10) 0.0433(10) Uani 1 1 d . . . C102 C 0.23751(19) 0.3619(3) 0.65564(9) 0.0443(11) Uani 1 1 d . . . H10C H 0.2133 0.4232 0.6602 0.066 Uiso 1 1 calc R . . H10D H 0.2154 0.3278 0.6306 0.066 Uiso 1 1 calc R . . H10E H 0.2765 0.3911 0.6558 0.066 Uiso 1 1 calc R . . N201 N -0.01780(17) 0.7434(3) 0.52856(9) 0.0527(9) Uani 1 1 d . . . C201 C -0.05118(19) 0.8127(3) 0.52961(9) 0.0363(9) Uani 1 1 d . . . C202 C -0.09188(18) 0.8999(3) 0.53199(9) 0.0400(10) Uani 1 1 d . . . H20A H -0.0933 0.9014 0.5579 0.06 Uiso 1 1 calc R . . H20B H -0.1328 0.8854 0.5133 0.06 Uiso 1 1 calc R . . H20C H -0.0773 0.9721 0.5264 0.06 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0454(16) 0.0269(12) 0.0089(10) 0.0014(9) 0.0067(11) -0.0032(11) C10 0.049(3) 0.036(2) 0.0148(17) 0.0062(14) 0.0093(17) 0.0028(18) C111 0.044(2) 0.036(2) 0.0221(19) 0.0074(17) 0.0151(18) 0.0049(18) N112 0.079(8) 0.027(4) 0.050(6) 0.014(4) 0.046(5) 0.015(5) N113 0.064(6) 0.038(3) 0.035(5) 0.019(5) 0.012(4) 0.011(4) N114 0.062(5) 0.041(6) 0.033(5) 0.007(4) 0.020(3) 0.006(4) N115 0.062(8) 0.062(7) 0.035(5) 0.006(4) 0.031(6) -0.004(6) C121 0.044(2) 0.036(2) 0.0221(19) 0.0074(17) 0.0151(18) 0.0049(18) N122 0.046(6) 0.040(4) 0.025(4) 0.011(4) 0.013(4) 0.012(4) N123 0.064(6) 0.038(3) 0.035(5) 0.019(5) 0.012(4) 0.011(4) N124 0.062(5) 0.041(6) 0.033(5) 0.007(4) 0.020(3) 0.006(4) N125 0.042(6) 0.028(5) 0.020(4) 0.000(3) 0.014(5) -0.005(4) C11 0.037(2) 0.0242(18) 0.0102(16) 0.0019(13) 0.0062(15) -0.0040(16) C12 0.041(2) 0.0275(18) 0.0098(16) -0.0002(13) 0.0103(16) -0.0008(16) C13 0.041(2) 0.0296(19) 0.0123(16) -0.0013(14) 0.0131(16) 0.0014(16) C14 0.041(2) 0.0215(17) 0.0098(15) 0.0029(13) 0.0058(16) 0.0001(16) C141 0.047(3) 0.033(2) 0.0211(18) 0.0014(15) 0.0156(18) 0.0020(18) C142 0.090(4) 0.037(2) 0.034(2) -0.0048(17) 0.031(2) -0.021(2) C143 0.061(3) 0.041(2) 0.035(2) 0.0141(17) 0.022(2) 0.009(2) C144 0.055(3) 0.046(2) 0.038(2) 0.0115(17) 0.023(2) 0.001(2) C15 0.042(2) 0.032(2) 0.0164(17) 0.0002(14) 0.0128(17) -0.0005(17) C16 0.040(2) 0.0279(19) 0.0121(16) 0.0001(13) 0.0086(16) 0.0027(16) C1 0.042(2) 0.030(2) 0.0156(16) 0.0025(14) 0.0096(16) 0.0034(16) O21 0.0409(16) 0.0291(13) 0.0184(12) 0.0005(10) 0.0081(11) 0.0033(11) C21 0.040(2) 0.0281(19) 0.0112(16) 0.0025(14) 0.0096(16) 0.0067(16) C22 0.044(2) 0.0298(19) 0.0124(16) 0.0009(14) 0.0139(16) 0.0025(17) C23 0.040(2) 0.042(2) 0.0139(17) -0.0036(15) 0.0087(16) -0.0047(18) C24 0.046(2) 0.033(2) 0.0147(17) -0.0033(14) 0.0120(17) 0.0069(18) C241 0.046(3) 0.039(2) 0.0209(18) -0.0049(16) 0.0067(18) 0.0082(19) C242 0.066(3) 0.052(3) 0.050(3) -0.016(2) -0.003(2) 0.023(2) C243 0.096(4) 0.047(2) 0.029(2) 0.0120(18) 0.034(2) 0.026(2) C244 0.052(3) 0.039(2) 0.032(2) -0.0037(16) 0.0173(19) 0.0078(19) C25 0.047(2) 0.0270(19) 0.0192(17) -0.0025(14) 0.0190(17) 0.0003(17) C26 0.040(2) 0.032(2) 0.0117(16) -0.0017(14) 0.0138(16) 0.0013(17) C2 0.044(2) 0.0291(19) 0.0153(17) 0.0006(14) 0.0162(16) 0.0011(17) O31 0.0454(16) 0.0278(13) 0.0147(11) 0.0017(9) 0.0081(11) -0.0022(11) C30 0.046(2) 0.0247(19) 0.0262(19) -0.0002(14) 0.0144(18) -0.0039(17) C311 0.050(3) 0.0282(19) 0.0176(17) -0.0016(15) 0.0159(17) 0.0002(17) N312 0.058(2) 0.0274(16) 0.0220(15) 0.0028(13) 0.0172(15) 0.0037(15) N313 0.076(3) 0.0333(18) 0.0212(15) 0.0058(13) 0.0177(17) 0.0042(17) N314 0.078(3) 0.0339(18) 0.0246(16) 0.0049(14) 0.0206(17) -0.0020(18) N315 0.063(2) 0.0322(17) 0.0161(14) 0.0045(12) 0.0127(15) 0.0021(16) C31 0.044(2) 0.0206(18) 0.0127(16) -0.0024(13) 0.0042(16) -0.0040(16) C32 0.049(2) 0.0249(18) 0.0138(16) -0.0045(14) 0.0109(17) -0.0024(17) C33 0.044(2) 0.0320(19) 0.0128(16) -0.0038(14) 0.0119(16) -0.0045(17) C34 0.039(2) 0.0319(19) 0.0108(16) -0.0028(14) 0.0087(16) -0.0042(17) C341 0.041(2) 0.037(2) 0.0148(16) 0.0014(15) 0.0075(16) 0.0008(18) C342 0.056(3) 0.051(2) 0.026(2) 0.0160(17) 0.0184(19) 0.008(2) C343 0.060(3) 0.042(2) 0.029(2) 0.0068(17) 0.010(2) 0.013(2) C344 0.054(3) 0.057(3) 0.0203(19) 0.0062(17) 0.0070(19) -0.011(2) C35 0.038(2) 0.0276(19) 0.0162(17) -0.0035(14) 0.0066(16) 0.0003(16) C36 0.038(2) 0.0223(17) 0.0146(16) 0.0001(13) 0.0099(16) -0.0008(15) C3 0.038(2) 0.0292(19) 0.0171(17) 0.0004(14) 0.0090(16) -0.0030(16) O41 0.0446(17) 0.0351(14) 0.0184(12) -0.0003(10) 0.0104(11) -0.0042(12) C41 0.038(2) 0.0301(19) 0.0147(16) 0.0058(14) 0.0104(16) 0.0125(17) C42 0.036(2) 0.0283(19) 0.0159(17) 0.0013(14) 0.0091(16) 0.0080(16) C43 0.039(2) 0.0266(19) 0.0250(18) 0.0023(14) 0.0141(17) 0.0040(16) C44 0.046(2) 0.0256(19) 0.0170(17) 0.0029(14) 0.0135(17) 0.0079(17) C441 0.048(3) 0.036(2) 0.0235(19) 0.0028(16) 0.0176(18) 0.0029(18) C442 0.088(4) 0.052(3) 0.037(2) -0.0004(19) 0.036(2) -0.006(2) C443 0.076(4) 0.087(4) 0.069(3) 0.047(3) 0.036(3) 0.034(3) C444 0.090(4) 0.060(3) 0.030(2) -0.0053(19) 0.036(2) -0.008(3) C45 0.043(2) 0.031(2) 0.0142(17) 0.0002(14) 0.0080(16) 0.0127(17) C46 0.037(2) 0.0313(19) 0.0151(16) 0.0001(14) 0.0111(16) 0.0105(16) C4 0.040(2) 0.0287(19) 0.0196(17) -0.0044(14) 0.0101(17) 0.0067(17) N101 0.072(3) 0.071(3) 0.035(2) 0.0061(18) 0.016(2) -0.011(2) C101 0.053(3) 0.053(3) 0.022(2) -0.0042(18) 0.011(2) -0.003(2) C102 0.061(3) 0.041(2) 0.029(2) 0.0046(17) 0.012(2) 0.001(2) N201 0.058(3) 0.059(2) 0.044(2) 0.0089(17) 0.0218(19) 0.001(2) C201 0.046(3) 0.039(2) 0.024(2) 0.0067(17) 0.0123(19) -0.007(2) C202 0.057(3) 0.040(2) 0.0248(19) -0.0017(16) 0.0173(19) -0.002(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 C11 1.410(3) . ? O11 C10 1.434(3) . ? C10 C111 1.482(4) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C10 H10F 0.99 . ? C10 H10G 0.99 . ? C111 N112 1.299(9) . ? C111 N115 1.394(17) . ? N112 N113 1.356(12) . ? N112 H112 0.88 . ? N113 N114 1.310(16) . ? N114 N115 1.33(2) . ? N122 N123 1.329(13) . ? N122 H122 0.88 . ? N123 N124 1.341(16) . ? N124 N125 1.44(2) . ? C11 C16 1.375(5) . ? C11 C12 1.398(4) . ? C12 C13 1.400(4) . ? C12 C2 1.499(5) . ? C13 C14 1.394(5) . ? C13 H13 0.95 . ? C14 C15 1.389(4) . ? C14 C141 1.529(4) . ? C141 C144 1.519(5) . ? C141 C143 1.536(5) . ? C141 C142 1.546(4) . ? C142 H14A 0.98 . ? C142 H14B 0.98 . ? C142 H14C 0.98 . ? C143 H14D 0.98 . ? C143 H14E 0.98 . ? C143 H14F 0.98 . ? C144 H14G 0.98 . ? C144 H14H 0.98 . ? C144 H14I 0.98 . ? C15 C16 1.399(4) . ? C15 H15 0.95 . ? C16 C1 1.524(4) . ? C1 C42 1.513(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? O21 C21 1.387(4) . ? O21 H21 0.84 . ? C21 C22 1.388(4) . ? C21 C26 1.404(4) . ? C22 C23 1.400(4) . ? C22 C3 1.517(4) . ? C23 C24 1.393(4) . ? C23 H23 0.95 . ? C24 C25 1.391(4) . ? C24 C241 1.532(4) . ? C241 C242 1.515(5) . ? C241 C244 1.522(4) . ? C241 C243 1.538(5) . ? C242 H24A 0.98 . ? C242 H24B 0.98 . ? C242 H24C 0.98 . ? C243 H24D 0.98 . ? C243 H24E 0.98 . ? C243 H24F 0.98 . ? C244 H24G 0.98 . ? C244 H24H 0.98 . ? C244 H24I 0.98 . ? C25 C26 1.396(4) . ? C25 H25 0.95 . ? C26 C2 1.528(4) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? O31 C31 1.409(3) . ? O31 C30 1.435(4) . ? C30 C311 1.489(4) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C311 N315 1.313(4) . ? C311 N312 1.325(4) . ? N312 N313 1.342(3) . ? N312 H312 0.88 . ? N313 N314 1.303(4) . ? N314 N315 1.358(3) . ? C31 C32 1.378(4) . ? C31 C36 1.385(5) . ? C32 C33 1.391(4) . ? C32 C4 1.514(5) . ? C33 C34 1.393(5) . ? C33 H33 0.95 . ? C34 C35 1.377(4) . ? C34 C341 1.544(4) . ? C341 C342 1.524(5) . ? C341 C343 1.527(5) . ? C341 C344 1.545(5) . ? C342 H34A 0.98 . ? C342 H34B 0.98 . ? C342 H34C 0.98 . ? C343 H34D 0.98 . ? C343 H34E 0.98 . ? C343 H34F 0.98 . ? C344 H34G 0.98 . ? C344 H34H 0.98 . ? C344 H34I 0.98 . ? C35 C36 1.397(4) . ? C35 H35 0.95 . ? C36 C3 1.520(4) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? O41 C41 1.371(4) . ? O41 H41 0.84 . ? C41 C46 1.394(4) . ? C41 C42 1.407(5) . ? C42 C43 1.378(4) . ? C43 C44 1.389(4) . ? C43 H43 0.95 . ? C44 C45 1.393(5) . ? C44 C441 1.524(4) . ? C441 C444 1.515(5) . ? C441 C442 1.530(5) . ? C441 C443 1.531(5) . ? C442 H44A 0.98 . ? C442 H44B 0.98 . ? C442 H44C 0.98 . ? C443 H44D 0.98 . ? C443 H44E 0.98 . ? C443 H44F 0.98 . ? C444 H44G 0.98 . ? C444 H44H 0.98 . ? C444 H44I 0.98 . ? C45 C46 1.380(4) . ? C45 H45 0.95 . ? C46 C4 1.530(5) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? N101 C101 1.138(4) . ? C101 C102 1.451(5) . ? C102 H10C 0.98 . ? C102 H10D 0.98 . ? C102 H10E 0.98 . ? N201 C201 1.152(5) . ? C201 C202 1.440(5) . ? C202 H20A 0.98 . ? C202 H20B 0.98 . ? C202 H20C 0.98 . ? 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 C11 O11 C10 111.3(2) . . ? O11 C10 C111 107.7(3) . . ? O11 C10 H10A 110.2 . . ? C111 C10 H10A 110.2 . . ? O11 C10 H10B 110.2 . . ? C111 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? O11 C10 H10F 111.8 . . ? C111 C10 H10F 107.9 . . ? O11 C10 H10G 111.8 . . ? C111 C10 H10G 107.9 . . ? H10F C10 H10G 109.6 . . ? N112 C111 N115 108.4(8) . . ? N112 C111 C10 129.4(5) . . ? N115 C111 C10 121.3(7) . . ? C111 N112 N113 110.2(8) . . ? C111 N112 H112 124.9 . . ? N113 N112 H112 124.9 . . ? N114 N113 N112 104.2(11) . . ? N113 N114 N115 114.0(15) . . ? N114 N115 C111 102.9(11) . . ? N123 N122 H122 125.6 . . ? N122 N123 N124 106.4(10) . . ? N123 N124 N125 108.2(14) . . ? C16 C11 C12 122.3(3) . . ? C16 C11 O11 119.5(3) . . ? C12 C11 O11 118.1(3) . . ? C11 C12 C13 117.6(3) . . ? C11 C12 C2 122.2(3) . . ? C13 C12 C2 120.2(3) . . ? C14 C13 C12 122.1(3) . . ? C14 C13 H13 119 . . ? C12 C13 H13 119 . . ? C15 C14 C13 117.5(3) . . ? C15 C14 C141 122.6(3) . . ? C13 C14 C141 119.9(3) . . ? C144 C141 C14 112.8(3) . . ? C144 C141 C143 108.8(3) . . ? C14 C141 C143 109.6(3) . . ? C144 C141 C142 108.3(3) . . ? C14 C141 C142 109.7(3) . . ? C143 C141 C142 107.5(3) . . ? C141 C142 H14A 109.5 . . ? C141 C142 H14B 109.5 . . ? H14A C142 H14B 109.5 . . ? C141 C142 H14C 109.5 . . ? H14A C142 H14C 109.5 . . ? H14B C142 H14C 109.5 . . ? C141 C143 H14D 109.5 . . ? C141 C143 H14E 109.5 . . ? H14D C143 H14E 109.5 . . ? C141 C143 H14F 109.5 . . ? H14D C143 H14F 109.5 . . ? H14E C143 H14F 109.5 . . ? C141 C144 H14G 109.5 . . ? C141 C144 H14H 109.5 . . ? H14G C144 H14H 109.5 . . ? C141 C144 H14I 109.5 . . ? H14G C144 H14I 109.5 . . ? H14H C144 H14I 109.5 . . ? C14 C15 C16 122.5(3) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C11 C16 C15 117.9(3) . . ? C11 C16 C1 122.3(3) . . ? C15 C16 C1 119.6(3) . . ? C42 C1 C16 110.9(3) . . ? C42 C1 H1A 109.5 . . ? C16 C1 H1A 109.5 . . ? C42 C1 H1B 109.5 . . ? C16 C1 H1B 109.5 . . ? H1A C1 H1B 108 . . ? C21 O21 H21 109.5 . . ? O21 C21 C22 116.7(3) . . ? O21 C21 C26 122.6(3) . . ? C22 C21 C26 120.7(3) . . ? C21 C22 C23 118.8(3) . . ? C21 C22 C3 122.4(3) . . ? C23 C22 C3 118.7(3) . . ? C24 C23 C22 122.5(3) . . ? C24 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? C25 C24 C23 116.9(3) . . ? C25 C24 C241 120.1(3) . . ? C23 C24 C241 123.0(3) . . ? C242 C241 C244 108.0(3) . . ? C242 C241 C24 111.9(3) . . ? C244 C241 C24 111.4(3) . . ? C242 C241 C243 109.6(3) . . ? C244 C241 C243 108.1(3) . . ? C24 C241 C243 107.7(3) . . ? C241 C242 H24A 109.5 . . ? C241 C242 H24B 109.5 . . ? H24A C242 H24B 109.5 . . ? C241 C242 H24C 109.5 . . ? H24A C242 H24C 109.5 . . ? H24B C242 H24C 109.5 . . ? C241 C243 H24D 109.5 . . ? C241 C243 H24E 109.5 . . ? H24D C243 H24E 109.5 . . ? C241 C243 H24F 109.5 . . ? H24D C243 H24F 109.5 . . ? H24E C243 H24F 109.5 . . ? C241 C244 H24G 109.5 . . ? C241 C244 H24H 109.5 . . ? H24G C244 H24H 109.5 . . ? C241 C244 H24I 109.5 . . ? H24G C244 H24I 109.5 . . ? H24H C244 H24I 109.5 . . ? C24 C25 C26 122.8(3) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? C25 C26 C21 118.3(3) . . ? C25 C26 C2 118.7(3) . . ? C21 C26 C2 122.9(3) . . ? C12 C2 C26 112.4(2) . . ? C12 C2 H2A 109.1 . . ? C26 C2 H2A 109.1 . . ? C12 C2 H2B 109.1 . . ? C26 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C31 O31 C30 113.0(2) . . ? O31 C30 C311 107.7(3) . . ? O31 C30 H30A 110.2 . . ? C311 C30 H30A 110.2 . . ? O31 C30 H30B 110.2 . . ? C311 C30 H30B 110.2 . . ? H30A C30 H30B 108.5 . . ? N315 C311 N312 109.5(3) . . ? N315 C311 C30 125.6(3) . . ? N312 C311 C30 124.9(3) . . ? C311 N312 N313 108.2(3) . . ? C311 N312 H312 125.9 . . ? N313 N312 H312 125.9 . . ? N314 N313 N312 106.5(3) . . ? N313 N314 N315 110.3(2) . . ? C311 N315 N314 105.5(2) . . ? C32 C31 C36 122.1(3) . . ? C32 C31 O31 117.4(3) . . ? C36 C31 O31 120.3(3) . . ? C31 C32 C33 118.0(3) . . ? C31 C32 C4 122.3(3) . . ? C33 C32 C4 119.5(3) . . ? C32 C33 C34 122.1(3) . . ? C32 C33 H33 118.9 . . ? C34 C33 H33 118.9 . . ? C35 C34 C33 117.7(3) . . ? C35 C34 C341 120.1(3) . . ? C33 C34 C341 122.2(3) . . ? C342 C341 C343 108.2(3) . . ? C342 C341 C34 111.0(3) . . ? C343 C341 C34 111.0(3) . . ? C342 C341 C344 108.9(3) . . ? C343 C341 C344 109.5(3) . . ? C34 C341 C344 108.2(3) . . ? C341 C342 H34A 109.5 . . ? C341 C342 H34B 109.5 . . ? H34A C342 H34B 109.5 . . ? C341 C342 H34C 109.5 . . ? H34A C342 H34C 109.5 . . ? H34B C342 H34C 109.5 . . ? C341 C343 H34D 109.5 . . ? C341 C343 H34E 109.5 . . ? H34D C343 H34E 109.5 . . ? C341 C343 H34F 109.5 . . ? H34D C343 H34F 109.5 . . ? H34E C343 H34F 109.5 . . ? C341 C344 H34G 109.5 . . ? C341 C344 H34H 109.5 . . ? H34G C344 H34H 109.5 . . ? C341 C344 H34I 109.5 . . ? H34G C344 H34I 109.5 . . ? H34H C344 H34I 109.5 . . ? C34 C35 C36 122.1(3) . . ? C34 C35 H35 118.9 . . ? C36 C35 H35 118.9 . . ? C31 C36 C35 117.9(3) . . ? C31 C36 C3 123.5(3) . . ? C35 C36 C3 118.4(3) . . ? C22 C3 C36 108.6(3) . . ? C22 C3 H3A 110 . . ? C36 C3 H3A 110 . . ? C22 C3 H3B 110 . . ? C36 C3 H3B 110 . . ? H3A C3 H3B 108.4 . . ? C41 O41 H41 109.5 . . ? O41 C41 C46 122.1(3) . . ? O41 C41 C42 117.8(3) . . ? C46 C41 C42 120.1(3) . . ? C43 C42 C41 118.7(3) . . ? C43 C42 C1 118.9(3) . . ? C41 C42 C1 122.2(3) . . ? C42 C43 C44 122.9(3) . . ? C42 C43 H43 118.5 . . ? C44 C43 H43 118.5 . . ? C43 C44 C45 116.4(3) . . ? C43 C44 C441 122.9(3) . . ? C45 C44 C441 120.7(3) . . ? C444 C441 C44 109.9(3) . . ? C444 C441 C442 108.2(3) . . ? C44 C441 C442 112.0(3) . . ? C444 C441 C443 109.1(3) . . ? C44 C441 C443 108.5(3) . . ? C442 C441 C443 109.0(3) . . ? C441 C442 H44A 109.5 . . ? C441 C442 H44B 109.5 . . ? H44A C442 H44B 109.5 . . ? C441 C442 H44C 109.5 . . ? H44A C442 H44C 109.5 . . ? H44B C442 H44C 109.5 . . ? C441 C443 H44D 109.5 . . ? C441 C443 H44E 109.5 . . ? H44D C443 H44E 109.5 . . ? C441 C443 H44F 109.5 . . ? H44D C443 H44F 109.5 . . ? H44E C443 H44F 109.5 . . ? C441 C444 H44G 109.5 . . ? C441 C444 H44H 109.5 . . ? H44G C444 H44H 109.5 . . ? C441 C444 H44I 109.5 . . ? H44G C444 H44I 109.5 . . ? H44H C444 H44I 109.5 . . ? C46 C45 C44 123.3(3) . . ? C46 C45 H45 118.4 . . ? C44 C45 H45 118.4 . . ? C45 C46 C41 118.5(3) . . ? C45 C46 C4 119.1(3) . . ? C41 C46 C4 122.1(3) . . ? C32 C4 C46 110.9(3) . . ? C32 C4 H4A 109.5 . . ? C46 C4 H4A 109.5 . . ? C32 C4 H4B 109.5 . . ? C46 C4 H4B 109.5 . . ? H4A C4 H4B 108 . . ? N101 C101 C102 179.0(4) . . ? C101 C102 H10C 109.5 . . ? C101 C102 H10D 109.5 . . ? H10C C102 H10D 109.5 . . ? C101 C102 H10E 109.5 . . ? H10C C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? N201 C201 C202 178.4(4) . . ? C201 C202 H20A 109.5 . . ? C201 C202 H20B 109.5 . . ? H20A C202 H20B 109.5 . . ? C201 C202 H20C 109.5 . . ? H20A C202 H20C 109.5 . . ? H20B C202 H20C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N112 H112 N201 0.88 2.01 2.808(10) 149.7 . N122 H122 O41 0.88 2.15 3.028(8) 171.4 . O21 H21 O11 0.84 1.94 2.757(3) 164.1 . N312 H312 O21 0.88 2.17 3.015(3) 162.2 . O41 H41 O31 0.84 1.98 2.816(3) 171.3 . #===END