# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email andreas.lemmerer@wits.ac.za loop_ _publ_author_name A.Lemmerer J.Bernstein M.Spackman data_FORM_I _database_code_depnum_ccdc_archive 'CCDC 845159' #TrackingRef '- Combined cif files.cif' _audit_creation_date 2009-09-23T07:55:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (adamantane-1-carboxylate-3,5,7-tricarboxylic acid).(hexamethylenetetraminium) Form I ; _chemical_formula_moiety 'C14 H15 O8, C6 H13 N4' _chemical_formula_sum 'C20 H28 N4 O8' _chemical_formula_weight 452.46 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4903(4) _cell_length_b 17.9055(4) _cell_length_c 14.3635(4) _cell_angle_alpha 90 _cell_angle_beta 112.635(1) _cell_angle_gamma 90 _cell_volume 4151.78(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6295 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.93 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 -1 0.05 0 1 1 0.05 0 1 -1 0.14 1 -6 6 0.15 3 0 -1 0.21 -3 -2 3 0.37 -7 2 0 0.24 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9354 _exptl_absorpt_correction_T_max 0.9778 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_number 41144 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 7721 _reflns_number_gt 4277 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0348P)^2^+6.0060P] 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_number_reflns 7721 _refine_ls_number_parameters 601 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.425 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # 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 C1 C 0.32247(16) 0.41261(15) 0.8274(2) 0.0279(6) Uani 1 1 d . . . C2 C 0.28116(17) 0.35001(16) 0.8646(2) 0.0314(6) Uani 1 1 d . . . H2A H 0.3232 0.3167 0.9089 0.038 Uiso 1 1 calc R . . H2B H 0.2449 0.3212 0.8075 0.038 Uiso 1 1 calc R . . C3 C 0.23047(17) 0.38388(15) 0.9220(2) 0.0300(6) Uani 1 1 d . . . C4 C 0.16322(17) 0.43517(16) 0.8500(2) 0.0342(7) Uani 1 1 d . . . H4A H 0.1268 0.4065 0.7928 0.041 Uiso 1 1 calc R . . H4B H 0.1303 0.4561 0.8847 0.041 Uiso 1 1 calc R . . C5 C 0.20358(17) 0.49845(16) 0.8128(2) 0.0323(7) Uani 1 1 d . . . C6 C 0.26148(17) 0.54317(16) 0.9043(2) 0.0341(7) Uani 1 1 d . . . H6A H 0.2869 0.5835 0.8814 0.041 Uiso 1 1 calc R . . H6B H 0.2297 0.5648 0.9399 0.041 Uiso 1 1 calc R . . C7 C 0.32892(17) 0.49217(15) 0.9756(2) 0.0307(6) Uani 1 1 d . . . C8 C 0.28814(18) 0.42897(16) 1.0132(2) 0.0342(7) Uani 1 1 d . . . H8A H 0.3305 0.3965 1.0588 0.041 Uiso 1 1 calc R . . H8B H 0.2566 0.45 1.0496 0.041 Uiso 1 1 calc R . . C9 C 0.37978(17) 0.45789(16) 0.9188(2) 0.0304(6) Uani 1 1 d . . . H9A H 0.4065 0.4974 0.8962 0.036 Uiso 1 1 calc R . . H9B H 0.4225 0.4256 0.9639 0.036 Uiso 1 1 calc R . . C10 C 0.25466(17) 0.46441(16) 0.7565(2) 0.0328(7) Uani 1 1 d . . . H10A H 0.2185 0.4363 0.6987 0.039 Uiso 1 1 calc R . . H10B H 0.28 0.5041 0.7323 0.039 Uiso 1 1 calc R . . C11 C 0.37108(18) 0.38081(16) 0.7673(2) 0.0326(7) Uani 1 1 d . . . C12 C 0.18967(19) 0.32006(17) 0.9556(2) 0.0376(7) Uani 1 1 d . . . C13 C 0.13934(19) 0.55011(19) 0.7391(2) 0.0403(8) Uani 1 1 d . . . C14 C 0.38698(19) 0.53748(18) 1.0639(2) 0.0372(7) Uani 1 1 d . . . O1 O 0.35154(15) 0.31834(12) 0.72549(18) 0.0514(6) Uani 1 1 d . . . O2 O 0.42690(13) 0.41954(12) 0.75585(16) 0.0458(6) Uani 1 1 d . . . O3 O 0.24192(13) 0.27639(12) 1.02428(16) 0.0428(5) Uani 1 1 d . . . H3 H 0.213(2) 0.234(2) 1.032(3) 0.064 Uiso 1 1 d . . . O4 O 0.11654(15) 0.30768(17) 0.9198(3) 0.0907(11) Uani 1 1 d . . . O5 O 0.07041(16) 0.51575(17) 0.6876(2) 0.0829(10) Uani 1 1 d . . . H5 H 0.034(3) 0.542(3) 0.646(4) 0.124 Uiso 1 1 d . . . O6 O 0.15073(16) 0.61456(14) 0.7271(2) 0.0734(8) Uani 1 1 d . . . O7 O 0.44820(15) 0.49767(13) 1.12841(18) 0.0518(6) Uani 1 1 d . . . H7 H 0.488(2) 0.529(2) 1.166(3) 0.078 Uiso 1 1 d . . . O8 O 0.37919(18) 0.60326(14) 1.0745(2) 0.0786(9) Uani 1 1 d . . . C15 C 0.17566(17) 0.43131(15) 0.4178(2) 0.0305(6) Uani 1 1 d . . . C16 C 0.12495(18) 0.47700(16) 0.3235(2) 0.0350(7) Uani 1 1 d . . . H16A H 0.0918 0.5139 0.3405 0.042 Uiso 1 1 calc R . . H16B H 0.0877 0.4442 0.2723 0.042 Uiso 1 1 calc R . . C17 C 0.18358(18) 0.51652(16) 0.2819(2) 0.0338(7) Uani 1 1 d . . . C18 C 0.23639(19) 0.45806(17) 0.2546(2) 0.0372(7) Uani 1 1 d . . . H18A H 0.2006 0.4251 0.2025 0.045 Uiso 1 1 calc R . . H18B H 0.2734 0.483 0.2288 0.045 Uiso 1 1 calc R . . C19 C 0.28704(18) 0.41246(16) 0.3486(2) 0.0337(7) Uani 1 1 d . . . C20 C 0.34476(18) 0.46477(17) 0.4300(2) 0.0381(7) Uani 1 1 d . . . H20A H 0.3825 0.4894 0.405 0.046 Uiso 1 1 calc R . . H20B H 0.3774 0.4361 0.4893 0.046 Uiso 1 1 calc R . . C21 C 0.29297(18) 0.52350(17) 0.4580(2) 0.0370(7) Uani 1 1 d . . . C22 C 0.24159(19) 0.56896(17) 0.3638(2) 0.0376(7) Uani 1 1 d . . . H22A H 0.2783 0.5947 0.3382 0.045 Uiso 1 1 calc R . . H22B H 0.2091 0.6062 0.3814 0.045 Uiso 1 1 calc R . . C23 C 0.23426(18) 0.48353(17) 0.4988(2) 0.0354(7) Uani 1 1 d . . . H23A H 0.2664 0.4548 0.5583 0.042 Uiso 1 1 calc R . . H23B H 0.2022 0.5202 0.5179 0.042 Uiso 1 1 calc R . . C24 C 0.22795(18) 0.37354(16) 0.3900(2) 0.0338(7) Uani 1 1 d . . . H24A H 0.1918 0.3397 0.3395 0.041 Uiso 1 1 calc R . . H24B H 0.2599 0.3445 0.4492 0.041 Uiso 1 1 calc R . . C25 C 0.12140(19) 0.39043(17) 0.4643(2) 0.0355(7) Uani 1 1 d . . . C26 C 0.1350(2) 0.56229(19) 0.1893(2) 0.0445(8) Uani 1 1 d . . . C27 C 0.3347(2) 0.34961(18) 0.3240(3) 0.0427(8) Uani 1 1 d . . . C28 C 0.3491(2) 0.5762(2) 0.5387(3) 0.0503(9) Uani 1 1 d . . . O9 O 0.04586(14) 0.40272(16) 0.4348(2) 0.0727(9) Uani 1 1 d . . . O10 O 0.15660(13) 0.34497(11) 0.53483(16) 0.0419(5) Uani 1 1 d . . . O11 O 0.18256(17) 0.59829(18) 0.1517(2) 0.0810(10) Uani 1 1 d . . . H11 H 0.145(3) 0.632(3) 0.095(4) 0.122 Uiso 1 1 d . . . O12 O 0.06214(18) 0.5686(2) 0.1532(3) 0.1047(13) Uani 1 1 d . . . O13 O 0.28939(16) 0.31211(15) 0.24249(19) 0.0598(7) Uani 1 1 d . . . H13 H 0.317(3) 0.265(2) 0.244(3) 0.09 Uiso 1 1 d . . . O14 O 0.40431(16) 0.33149(16) 0.3778(2) 0.0771(9) Uani 1 1 d . . . O15 O 0.30694(18) 0.62440(17) 0.5702(3) 0.0856(10) Uani 1 1 d . . . H15 H 0.348(3) 0.653(3) 0.628(4) 0.128 Uiso 1 1 d . . . O16 O 0.42224(17) 0.57682(19) 0.5704(2) 0.0918(11) Uani 1 1 d . . . C29 C 0.5590(3) 0.3445(2) 0.6575(3) 0.0628(11) Uani 1 1 d . . . H29A H 0.5298 0.3727 0.5963 0.075 Uiso 1 1 calc R . . H29B H 0.5885 0.3795 0.7107 0.075 Uiso 1 1 calc R . . C30 C 0.5717(2) 0.2434(2) 0.5616(3) 0.0638(11) Uani 1 1 d . . . H30A H 0.6109 0.2102 0.5498 0.077 Uiso 1 1 calc R . . H30B H 0.5428 0.2712 0.5 0.077 Uiso 1 1 calc R . . C31 C 0.5553(3) 0.1583(2) 0.6796(4) 0.0829(14) Uani 1 1 d . . . H31A H 0.5938 0.1237 0.6689 0.1 Uiso 1 1 calc R . . H31B H 0.5158 0.1294 0.6971 0.1 Uiso 1 1 calc R . . C32 C 0.6587(2) 0.2532(3) 0.7343(3) 0.0696(12) Uani 1 1 d . . . H32A H 0.6883 0.288 0.788 0.084 Uiso 1 1 calc R . . H32B H 0.6991 0.2203 0.7248 0.084 Uiso 1 1 calc R . . C33 C 0.5424(2) 0.25787(19) 0.7807(2) 0.0471(8) Uani 1 1 d . . . H33A H 0.5707 0.2918 0.836 0.057 Uiso 1 1 calc R . . H33B H 0.5028 0.229 0.7981 0.057 Uiso 1 1 calc R . . C34 C 0.4529(2) 0.2490(3) 0.6027(3) 0.0800(14) Uani 1 1 d . . . H34A H 0.4129 0.2206 0.6198 0.096 Uiso 1 1 calc R . . H34B H 0.4233 0.2768 0.5415 0.096 Uiso 1 1 calc R . . N1 N 0.49814(19) 0.30128(19) 0.6861(2) 0.0567(9) Uani 1 1 d . . . H1 H 0.464(3) 0.332(2) 0.700(3) 0.085 Uiso 1 1 d . . . N2 N 0.61603(17) 0.29490(17) 0.6416(2) 0.0526(8) Uani 1 1 d . . . N3 N 0.5115(2) 0.1989(2) 0.5868(3) 0.0757(11) Uani 1 1 d . . . N4 N 0.60149(18) 0.20863(15) 0.7648(2) 0.0509(7) Uani 1 1 d . . . C35 C 0.0648(2) 0.2406(3) 0.6347(4) 0.0758(13) Uani 1 1 d . . . H35A H 0.0993 0.2089 0.6122 0.091 Uiso 1 1 calc R . . H35B H 0.1007 0.2722 0.6887 0.091 Uiso 1 1 calc R . . C36 C -0.0388(3) 0.1490(2) 0.5896(3) 0.0622(10) Uani 1 1 d . . . H36A H -0.0714 0.1175 0.6152 0.075 Uiso 1 1 calc R . . H36B H -0.0053 0.1167 0.5663 0.075 Uiso 1 1 calc R . . C37 C -0.1434(2) 0.2425(2) 0.5428(3) 0.0698(12) Uani 1 1 d . . . H37A H -0.1802 0.2727 0.4877 0.084 Uiso 1 1 calc R . . H37B H -0.1772 0.2122 0.5681 0.084 Uiso 1 1 calc R . . C38 C -0.0359(3) 0.2456(3) 0.7045(3) 0.0725(13) Uani 1 1 d . . . H38A H -0.0686 0.2158 0.732 0.087 Uiso 1 1 calc R . . H38B H -0.0001 0.2777 0.7579 0.087 Uiso 1 1 calc R . . C39 C -0.0417(3) 0.3373(2) 0.5852(3) 0.0714(12) Uani 1 1 d . . . H39A H -0.0065 0.37 0.6383 0.086 Uiso 1 1 calc R . . H39B H -0.0775 0.3681 0.5302 0.086 Uiso 1 1 calc R . . C40 C -0.0453(2) 0.2387(2) 0.4658(3) 0.0591(10) Uani 1 1 d . . . H40A H -0.0812 0.2691 0.4103 0.071 Uiso 1 1 calc R . . H40B H -0.0123 0.2071 0.4409 0.071 Uiso 1 1 calc R . . N5 N 0.0106(2) 0.28808(19) 0.5490(3) 0.0652(10) Uani 1 1 d . . . H5A H 0.036(3) 0.318(3) 0.516(3) 0.098 Uiso 1 1 d . . . N6 N 0.0153(2) 0.19578(19) 0.6708(2) 0.0664(9) Uani 1 1 d . . . N7 N -0.09470(17) 0.19301(16) 0.5044(2) 0.0478(7) Uani 1 1 d . . . N8 N -0.09090(19) 0.29146(19) 0.6230(3) 0.0614(9) 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 C1 0.0265(14) 0.0303(15) 0.0290(15) -0.0034(12) 0.0130(12) -0.0020(12) C2 0.0322(15) 0.0289(15) 0.0348(16) -0.0041(13) 0.0147(13) -0.0021(13) C3 0.0294(15) 0.0288(15) 0.0339(16) -0.0020(13) 0.0145(13) -0.0022(12) C4 0.0310(15) 0.0355(17) 0.0381(17) -0.0007(14) 0.0155(14) 0.0010(13) C5 0.0311(15) 0.0320(16) 0.0341(16) 0.0031(13) 0.0129(13) 0.0027(13) C6 0.0367(16) 0.0296(16) 0.0399(17) -0.0011(14) 0.0190(14) 0.0005(13) C7 0.0313(15) 0.0280(15) 0.0327(16) -0.0056(13) 0.0121(13) -0.0036(12) C8 0.0401(17) 0.0334(16) 0.0322(16) -0.0037(13) 0.0171(14) -0.0028(14) C9 0.0313(15) 0.0289(15) 0.0333(16) -0.0045(13) 0.0150(13) -0.0032(12) C10 0.0322(15) 0.0358(16) 0.0309(16) 0.0021(13) 0.0129(13) 0.0005(13) C11 0.0331(16) 0.0336(17) 0.0328(16) -0.0008(14) 0.0143(13) 0.0013(13) C12 0.0339(17) 0.0379(18) 0.0452(19) 0.0010(15) 0.0197(15) -0.0005(14) C13 0.0355(18) 0.043(2) 0.0448(19) 0.0047(16) 0.0185(15) 0.0068(15) C14 0.0417(18) 0.0358(18) 0.0372(18) -0.0073(15) 0.0184(15) -0.0044(15) O1 0.0695(16) 0.0366(13) 0.0673(16) -0.0149(12) 0.0477(14) -0.0100(12) O2 0.0413(12) 0.0543(14) 0.0502(14) -0.0182(11) 0.0269(11) -0.0156(11) O3 0.0436(13) 0.0369(12) 0.0468(14) 0.0055(11) 0.0161(11) -0.0081(10) O4 0.0367(15) 0.088(2) 0.134(3) 0.057(2) 0.0177(16) -0.0081(14) O5 0.0451(16) 0.070(2) 0.102(2) 0.0424(17) -0.0063(16) -0.0018(14) O6 0.0670(18) 0.0404(15) 0.092(2) 0.0170(15) 0.0072(16) 0.0076(13) O7 0.0460(14) 0.0414(14) 0.0534(15) -0.0111(12) 0.0031(12) -0.0049(11) O8 0.087(2) 0.0423(16) 0.076(2) -0.0244(14) -0.0017(16) 0.0034(14) C15 0.0327(15) 0.0281(15) 0.0314(16) 0.0018(13) 0.0130(13) -0.0009(12) C16 0.0342(16) 0.0323(16) 0.0377(17) 0.0025(14) 0.0130(14) 0.0008(13) C17 0.0352(16) 0.0322(16) 0.0331(16) 0.0060(13) 0.0124(13) 0.0032(13) C18 0.0455(18) 0.0369(17) 0.0319(16) 0.0039(14) 0.0178(14) 0.0020(14) C19 0.0391(17) 0.0304(16) 0.0351(17) 0.0026(13) 0.0183(14) 0.0002(13) C20 0.0330(16) 0.0402(18) 0.0418(18) 0.0056(15) 0.0150(14) 0.0004(14) C21 0.0376(17) 0.0343(17) 0.0385(18) -0.0036(14) 0.0140(14) -0.0062(14) C22 0.0439(18) 0.0314(17) 0.0404(18) 0.0021(14) 0.0195(15) -0.0032(14) C23 0.0393(17) 0.0391(17) 0.0275(16) -0.0020(13) 0.0126(14) -0.0041(14) C24 0.0370(16) 0.0302(16) 0.0353(17) 0.0014(13) 0.0150(14) 0.0007(13) C25 0.0401(18) 0.0315(16) 0.0382(18) 0.0010(14) 0.0186(15) -0.0002(14) C26 0.043(2) 0.048(2) 0.0433(19) 0.0125(16) 0.0174(16) 0.0045(16) C27 0.046(2) 0.0420(19) 0.048(2) 0.0035(17) 0.0264(17) 0.0044(16) C28 0.050(2) 0.049(2) 0.050(2) -0.0051(18) 0.0167(18) -0.0127(18) O9 0.0339(13) 0.101(2) 0.084(2) 0.0538(17) 0.0235(13) 0.0128(14) O10 0.0498(13) 0.0361(12) 0.0458(13) 0.0114(11) 0.0251(11) 0.0088(10) O11 0.0575(17) 0.104(2) 0.081(2) 0.0610(19) 0.0266(15) 0.0108(16) O12 0.0510(18) 0.147(3) 0.103(2) 0.082(2) 0.0159(17) 0.0100(19) O13 0.0735(18) 0.0530(16) 0.0501(15) -0.0077(13) 0.0206(14) 0.0203(14) O14 0.0482(16) 0.075(2) 0.099(2) -0.0200(17) 0.0180(16) 0.0173(14) O15 0.0664(19) 0.084(2) 0.101(2) -0.0582(19) 0.0267(17) -0.0163(16) O16 0.0491(17) 0.114(3) 0.102(2) -0.049(2) 0.0173(16) -0.0262(17) C29 0.093(3) 0.045(2) 0.061(2) 0.0108(19) 0.041(2) 0.011(2) C30 0.072(3) 0.076(3) 0.059(2) -0.009(2) 0.044(2) 0.007(2) C31 0.126(4) 0.040(2) 0.107(4) -0.021(3) 0.071(3) -0.012(3) C32 0.039(2) 0.094(3) 0.072(3) 0.018(3) 0.016(2) 0.004(2) C33 0.056(2) 0.048(2) 0.0402(19) -0.0024(16) 0.0216(17) -0.0002(17) C34 0.045(2) 0.141(4) 0.051(2) -0.012(3) 0.0142(19) -0.019(3) N1 0.0526(18) 0.078(2) 0.0448(18) 0.0016(16) 0.0248(15) 0.0288(17) N2 0.0494(17) 0.0579(19) 0.0554(19) 0.0044(16) 0.0257(15) -0.0035(15) N3 0.099(3) 0.076(2) 0.056(2) -0.033(2) 0.035(2) -0.028(2) N4 0.0539(17) 0.0408(16) 0.0582(19) 0.0125(15) 0.0219(15) 0.0086(14) C35 0.045(2) 0.084(3) 0.090(3) -0.027(3) 0.017(2) -0.010(2) C36 0.081(3) 0.043(2) 0.065(3) 0.001(2) 0.031(2) -0.009(2) C37 0.044(2) 0.090(3) 0.077(3) -0.036(3) 0.025(2) -0.005(2) C38 0.090(3) 0.091(3) 0.045(2) -0.018(2) 0.036(2) -0.035(3) C39 0.101(3) 0.038(2) 0.080(3) -0.013(2) 0.039(3) -0.006(2) C40 0.078(3) 0.063(2) 0.045(2) -0.0025(19) 0.033(2) 0.002(2) N5 0.085(2) 0.056(2) 0.077(2) -0.0052(18) 0.056(2) -0.0263(19) N6 0.074(2) 0.066(2) 0.0488(19) 0.0053(17) 0.0125(18) -0.0046(19) N7 0.0476(16) 0.0524(18) 0.0464(17) -0.0156(14) 0.0214(14) -0.0085(14) N8 0.0572(19) 0.069(2) 0.066(2) -0.0283(18) 0.0316(18) -0.0070(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C11 1.534(4) . ? C1 C2 1.537(4) . ? C1 C10 1.541(4) . ? C1 C9 1.541(4) . ? C2 C3 1.548(4) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C12 1.521(4) . ? C3 C4 1.537(4) . ? C3 C8 1.539(4) . ? C4 C5 1.535(4) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C13 1.524(4) . ? C5 C6 1.539(4) . ? C5 C10 1.543(4) . ? C6 C7 1.531(4) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 C14 1.519(4) . ? C7 C8 1.542(4) . ? C7 C9 1.547(4) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 O1 1.254(3) . ? C11 O2 1.259(3) . ? C12 O4 1.202(4) . ? C12 O3 1.313(4) . ? C13 O6 1.195(4) . ? C13 O5 1.301(4) . ? C14 O8 1.202(4) . ? C14 O7 1.323(4) . ? O3 H3 0.94(4) . ? O5 H5 0.83(5) . ? O7 H7 0.90(4) . ? C15 C24 1.532(4) . ? C15 C23 1.536(4) . ? C15 C16 1.539(4) . ? C15 C25 1.539(4) . ? C16 C17 1.543(4) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C26 1.514(4) . ? C17 C22 1.542(4) . ? C17 C18 1.543(4) . ? C18 C19 1.534(4) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C19 C27 1.521(4) . ? C19 C20 1.534(4) . ? C19 C24 1.543(4) . ? C20 C21 1.539(4) . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C21 C28 1.524(4) . ? C21 C22 1.538(4) . ? C21 C23 1.540(4) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? C25 O9 1.242(4) . ? C25 O10 1.260(3) . ? C26 O12 1.182(4) . ? C26 O11 1.321(4) . ? C27 O14 1.209(4) . ? C27 O13 1.317(4) . ? C28 O16 1.182(4) . ? C28 O15 1.322(4) . ? O11 H11 1.02(5) . ? O13 H13 0.97(4) . ? O15 H15 1.01(5) . ? C29 N2 1.418(4) . ? C29 N1 1.495(5) . ? C29 H29A 0.97 . ? C29 H29B 0.97 . ? C30 N2 1.444(5) . ? C30 N3 1.474(5) . ? C30 H30A 0.97 . ? C30 H30B 0.97 . ? C31 N3 1.451(6) . ? C31 N4 1.483(5) . ? C31 H31A 0.97 . ? C31 H31B 0.97 . ? C32 N2 1.457(5) . ? C32 N4 1.472(5) . ? C32 H32A 0.97 . ? C32 H32B 0.97 . ? C33 N4 1.443(4) . ? C33 N1 1.497(4) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 N3 1.444(5) . ? C34 N1 1.486(5) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? N1 H1 0.89(4) . ? C35 N6 1.417(5) . ? C35 N5 1.497(5) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 N6 1.452(5) . ? C36 N7 1.468(5) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 N8 1.458(5) . ? C37 N7 1.475(4) . ? C37 H37A 0.97 . ? C37 H37B 0.97 . ? C38 N8 1.451(5) . ? C38 N6 1.472(5) . ? C38 H38A 0.97 . ? C38 H38B 0.97 . ? C39 N8 1.438(5) . ? C39 N5 1.500(5) . ? C39 H39A 0.97 . ? C39 H39B 0.97 . ? C40 N7 1.445(4) . ? C40 N5 1.505(5) . ? C40 H40A 0.97 . ? C40 H40B 0.97 . ? N5 H5A 0.93(5) . ? 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 C1 C2 111.2(2) . . ? C11 C1 C10 107.7(2) . . ? C2 C1 C10 108.9(2) . . ? C11 C1 C9 110.8(2) . . ? C2 C1 C9 109.0(2) . . ? C10 C1 C9 109.2(2) . . ? C1 C2 C3 110.0(2) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C12 C3 C4 109.4(2) . . ? C12 C3 C8 111.0(2) . . ? C4 C3 C8 109.9(2) . . ? C12 C3 C2 108.0(2) . . ? C4 C3 C2 108.8(2) . . ? C8 C3 C2 109.7(2) . . ? C5 C4 C3 109.9(2) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C13 C5 C4 112.0(2) . . ? C13 C5 C6 110.1(2) . . ? C4 C5 C6 109.1(2) . . ? C13 C5 C10 107.2(2) . . ? C4 C5 C10 109.1(2) . . ? C6 C5 C10 109.2(2) . . ? C7 C6 C5 110.2(2) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C14 C7 C6 109.6(2) . . ? C14 C7 C8 110.5(2) . . ? C6 C7 C8 109.3(2) . . ? C14 C7 C9 108.5(2) . . ? C6 C7 C9 109.6(2) . . ? C8 C7 C9 109.3(2) . . ? C3 C8 C7 109.1(2) . . ? C3 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? C3 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C1 C9 C7 109.9(2) . . ? C1 C9 H9A 109.7 . . ? C7 C9 H9A 109.7 . . ? C1 C9 H9B 109.7 . . ? C7 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C1 C10 C5 110.2(2) . . ? C1 C10 H10A 109.6 . . ? C5 C10 H10A 109.6 . . ? C1 C10 H10B 109.6 . . ? C5 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O1 C11 O2 120.7(3) . . ? O1 C11 C1 119.5(3) . . ? O2 C11 C1 119.6(3) . . ? O4 C12 O3 122.0(3) . . ? O4 C12 C3 123.7(3) . . ? O3 C12 C3 114.2(3) . . ? O6 C13 O5 123.0(3) . . ? O6 C13 C5 124.5(3) . . ? O5 C13 C5 112.5(3) . . ? O8 C14 O7 122.7(3) . . ? O8 C14 C7 123.8(3) . . ? O7 C14 C7 113.4(3) . . ? C12 O3 H3 109(2) . . ? C13 O5 H5 116(4) . . ? C14 O7 H7 109(3) . . ? C24 C15 C23 108.5(2) . . ? C24 C15 C16 109.2(2) . . ? C23 C15 C16 109.5(2) . . ? C24 C15 C25 108.8(2) . . ? C23 C15 C25 107.7(2) . . ? C16 C15 C25 113.1(2) . . ? C15 C16 C17 109.9(2) . . ? C15 C16 H16A 109.7 . . ? C17 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? C17 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C26 C17 C22 108.8(3) . . ? C26 C17 C16 110.9(2) . . ? C22 C17 C16 108.9(2) . . ? C26 C17 C18 109.4(2) . . ? C22 C17 C18 108.9(2) . . ? C16 C17 C18 109.8(2) . . ? C19 C18 C17 109.7(2) . . ? C19 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? C19 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C27 C19 C18 111.8(2) . . ? C27 C19 C20 111.7(3) . . ? C18 C19 C20 109.5(2) . . ? C27 C19 C24 105.3(2) . . ? C18 C19 C24 109.5(2) . . ? C20 C19 C24 108.9(2) . . ? C19 C20 C21 109.6(2) . . ? C19 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? C19 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? C28 C21 C22 109.2(3) . . ? C28 C21 C20 110.5(3) . . ? C22 C21 C20 109.6(2) . . ? C28 C21 C23 109.1(3) . . ? C22 C21 C23 109.3(2) . . ? C20 C21 C23 109.1(2) . . ? C21 C22 C17 109.8(2) . . ? C21 C22 H22A 109.7 . . ? C17 C22 H22A 109.7 . . ? C21 C22 H22B 109.7 . . ? C17 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C15 C23 C21 110.1(2) . . ? C15 C23 H23A 109.6 . . ? C21 C23 H23A 109.6 . . ? C15 C23 H23B 109.6 . . ? C21 C23 H23B 109.6 . . ? H23A C23 H23B 108.2 . . ? C15 C24 C19 110.6(2) . . ? C15 C24 H24A 109.5 . . ? C19 C24 H24A 109.5 . . ? C15 C24 H24B 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? O9 C25 O10 121.0(3) . . ? O9 C25 C15 121.3(3) . . ? O10 C25 C15 117.6(3) . . ? O12 C26 O11 121.1(3) . . ? O12 C26 C17 125.7(3) . . ? O11 C26 C17 113.3(3) . . ? O14 C27 O13 123.0(3) . . ? O14 C27 C19 123.9(3) . . ? O13 C27 C19 112.8(3) . . ? O16 C28 O15 121.7(3) . . ? O16 C28 C21 125.7(4) . . ? O15 C28 C21 112.6(3) . . ? C26 O11 H11 108(3) . . ? C27 O13 H13 108(3) . . ? C28 O15 H15 108(3) . . ? N2 C29 N1 109.9(3) . . ? N2 C29 H29A 109.7 . . ? N1 C29 H29A 109.7 . . ? N2 C29 H29B 109.7 . . ? N1 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? N2 C30 N3 111.4(3) . . ? N2 C30 H30A 109.3 . . ? N3 C30 H30A 109.3 . . ? N2 C30 H30B 109.3 . . ? N3 C30 H30B 109.3 . . ? H30A C30 H30B 108 . . ? N3 C31 N4 112.4(3) . . ? N3 C31 H31A 109.1 . . ? N4 C31 H31A 109.1 . . ? N3 C31 H31B 109.1 . . ? N4 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? N2 C32 N4 112.4(3) . . ? N2 C32 H32A 109.1 . . ? N4 C32 H32A 109.1 . . ? N2 C32 H32B 109.1 . . ? N4 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? N4 C33 N1 108.9(3) . . ? N4 C33 H33A 109.9 . . ? N1 C33 H33A 109.9 . . ? N4 C33 H33B 109.9 . . ? N1 C33 H33B 109.9 . . ? H33A C33 H33B 108.3 . . ? N3 C34 N1 109.2(3) . . ? N3 C34 H34A 109.8 . . ? N1 C34 H34A 109.8 . . ? N3 C34 H34B 109.8 . . ? N1 C34 H34B 109.8 . . ? H34A C34 H34B 108.3 . . ? C34 N1 C29 108.6(3) . . ? C34 N1 C33 109.5(3) . . ? C29 N1 C33 110.2(3) . . ? C34 N1 H1 112(3) . . ? C29 N1 H1 111(3) . . ? C33 N1 H1 106(3) . . ? C29 N2 C30 109.4(3) . . ? C29 N2 C32 108.5(3) . . ? C30 N2 C32 109.3(3) . . ? C34 N3 C31 108.8(3) . . ? C34 N3 C30 108.7(3) . . ? C31 N3 C30 108.8(4) . . ? C33 N4 C32 109.0(3) . . ? C33 N4 C31 107.8(3) . . ? C32 N4 C31 107.6(3) . . ? N6 C35 N5 109.9(3) . . ? N6 C35 H35A 109.7 . . ? N5 C35 H35A 109.7 . . ? N6 C35 H35B 109.7 . . ? N5 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? N6 C36 N7 112.3(3) . . ? N6 C36 H36A 109.2 . . ? N7 C36 H36A 109.2 . . ? N6 C36 H36B 109.2 . . ? N7 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? N8 C37 N7 112.2(3) . . ? N8 C37 H37A 109.2 . . ? N7 C37 H37A 109.2 . . ? N8 C37 H37B 109.2 . . ? N7 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? N8 C38 N6 112.0(3) . . ? N8 C38 H38A 109.2 . . ? N6 C38 H38A 109.2 . . ? N8 C38 H38B 109.2 . . ? N6 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? N8 C39 N5 109.2(3) . . ? N8 C39 H39A 109.8 . . ? N5 C39 H39A 109.8 . . ? N8 C39 H39B 109.8 . . ? N5 C39 H39B 109.8 . . ? H39A C39 H39B 108.3 . . ? N7 C40 N5 109.2(3) . . ? N7 C40 H40A 109.8 . . ? N5 C40 H40A 109.8 . . ? N7 C40 H40B 109.8 . . ? N5 C40 H40B 109.8 . . ? H40A C40 H40B 108.3 . . ? C35 N5 C39 109.0(3) . . ? C35 N5 C40 109.3(3) . . ? C39 N5 C40 108.9(3) . . ? C35 N5 H5A 118(3) . . ? C39 N5 H5A 108(3) . . ? C40 N5 H5A 103(3) . . ? C35 N6 C36 109.5(3) . . ? C35 N6 C38 108.2(3) . . ? C36 N6 C38 108.9(3) . . ? C40 N7 C36 108.6(3) . . ? C40 N7 C37 108.6(3) . . ? C36 N7 C37 107.8(3) . . ? C39 N8 C38 108.7(3) . . ? C39 N8 C37 109.4(3) . . ? C38 N8 C37 108.5(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 C11 C1 C2 C3 -178.3(2) . . . . ? C10 C1 C2 C3 -59.8(3) . . . . ? C9 C1 C2 C3 59.3(3) . . . . ? C1 C2 C3 C12 179.0(2) . . . . ? C1 C2 C3 C4 60.4(3) . . . . ? C1 C2 C3 C8 -59.9(3) . . . . ? C12 C3 C4 C5 -178.2(2) . . . . ? C8 C3 C4 C5 59.7(3) . . . . ? C2 C3 C4 C5 -60.4(3) . . . . ? C3 C4 C5 C13 178.7(2) . . . . ? C3 C4 C5 C6 -59.1(3) . . . . ? C3 C4 C5 C10 60.2(3) . . . . ? C13 C5 C6 C7 -176.9(2) . . . . ? C4 C5 C6 C7 59.7(3) . . . . ? C10 C5 C6 C7 -59.4(3) . . . . ? C5 C6 C7 C14 178.4(2) . . . . ? C5 C6 C7 C8 -60.3(3) . . . . ? C5 C6 C7 C9 59.5(3) . . . . ? C12 C3 C8 C7 179.2(2) . . . . ? C4 C3 C8 C7 -59.7(3) . . . . ? C2 C3 C8 C7 59.9(3) . . . . ? C14 C7 C8 C3 -179.5(2) . . . . ? C6 C7 C8 C3 59.8(3) . . . . ? C9 C7 C8 C3 -60.2(3) . . . . ? C11 C1 C9 C7 177.6(2) . . . . ? C2 C1 C9 C7 -59.7(3) . . . . ? C10 C1 C9 C7 59.1(3) . . . . ? C14 C7 C9 C1 -178.9(2) . . . . ? C6 C7 C9 C1 -59.3(3) . . . . ? C8 C7 C9 C1 60.5(3) . . . . ? C11 C1 C10 C5 -179.8(2) . . . . ? C2 C1 C10 C5 59.5(3) . . . . ? C9 C1 C10 C5 -59.4(3) . . . . ? C13 C5 C10 C1 178.8(2) . . . . ? C4 C5 C10 C1 -59.7(3) . . . . ? C6 C5 C10 C1 59.4(3) . . . . ? C2 C1 C11 O1 24.2(4) . . . . ? C10 C1 C11 O1 -95.0(3) . . . . ? C9 C1 C11 O1 145.6(3) . . . . ? C2 C1 C11 O2 -159.8(3) . . . . ? C10 C1 C11 O2 81.0(3) . . . . ? C9 C1 C11 O2 -38.4(4) . . . . ? C4 C3 C12 O4 9.0(4) . . . . ? C8 C3 C12 O4 130.4(4) . . . . ? C2 C3 C12 O4 -109.3(4) . . . . ? C4 C3 C12 O3 -174.5(2) . . . . ? C8 C3 C12 O3 -53.0(3) . . . . ? C2 C3 C12 O3 67.2(3) . . . . ? C4 C5 C13 O6 152.1(3) . . . . ? C6 C5 C13 O6 30.5(4) . . . . ? C10 C5 C13 O6 -88.2(4) . . . . ? C4 C5 C13 O5 -29.7(4) . . . . ? C6 C5 C13 O5 -151.3(3) . . . . ? C10 C5 C13 O5 90.0(3) . . . . ? C6 C7 C14 O8 0.5(4) . . . . ? C8 C7 C14 O8 -120.1(4) . . . . ? C9 C7 C14 O8 120.1(4) . . . . ? C6 C7 C14 O7 -178.8(2) . . . . ? C8 C7 C14 O7 60.6(3) . . . . ? C9 C7 C14 O7 -59.2(3) . . . . ? C24 C15 C16 C17 -59.1(3) . . . . ? C23 C15 C16 C17 59.5(3) . . . . ? C25 C15 C16 C17 179.7(2) . . . . ? C15 C16 C17 C26 -179.6(2) . . . . ? C15 C16 C17 C22 -59.9(3) . . . . ? C15 C16 C17 C18 59.3(3) . . . . ? C26 C17 C18 C19 178.9(3) . . . . ? C22 C17 C18 C19 60.1(3) . . . . ? C16 C17 C18 C19 -59.1(3) . . . . ? C17 C18 C19 C27 175.1(2) . . . . ? C17 C18 C19 C20 -60.5(3) . . . . ? C17 C18 C19 C24 58.8(3) . . . . ? C27 C19 C20 C21 -175.6(2) . . . . ? C18 C19 C20 C21 60.0(3) . . . . ? C24 C19 C20 C21 -59.7(3) . . . . ? C19 C20 C21 C28 -179.9(2) . . . . ? C19 C20 C21 C22 -59.6(3) . . . . ? C19 C20 C21 C23 60.1(3) . . . . ? C28 C21 C22 C17 -179.2(3) . . . . ? C20 C21 C22 C17 59.6(3) . . . . ? C23 C21 C22 C17 -59.9(3) . . . . ? C26 C17 C22 C21 -178.9(2) . . . . ? C16 C17 C22 C21 60.1(3) . . . . ? C18 C17 C22 C21 -59.6(3) . . . . ? C24 C15 C23 C21 59.9(3) . . . . ? C16 C15 C23 C21 -59.2(3) . . . . ? C25 C15 C23 C21 177.5(2) . . . . ? C28 C21 C23 C15 178.7(3) . . . . ? C22 C21 C23 C15 59.4(3) . . . . ? C20 C21 C23 C15 -60.4(3) . . . . ? C23 C15 C24 C19 -59.9(3) . . . . ? C16 C15 C24 C19 59.4(3) . . . . ? C25 C15 C24 C19 -176.8(2) . . . . ? C27 C19 C24 C15 -179.9(2) . . . . ? C18 C19 C24 C15 -59.5(3) . . . . ? C20 C19 C24 C15 60.2(3) . . . . ? C24 C15 C25 O9 -130.6(3) . . . . ? C23 C15 C25 O9 112.0(3) . . . . ? C16 C15 C25 O9 -9.1(4) . . . . ? C24 C15 C25 O10 50.7(3) . . . . ? C23 C15 C25 O10 -66.7(3) . . . . ? C16 C15 C25 O10 172.2(3) . . . . ? C22 C17 C26 O12 -118.8(4) . . . . ? C16 C17 C26 O12 1.0(5) . . . . ? C18 C17 C26 O12 122.3(4) . . . . ? C22 C17 C26 O11 59.2(4) . . . . ? C16 C17 C26 O11 179.0(3) . . . . ? C18 C17 C26 O11 -59.7(4) . . . . ? C18 C19 C27 O14 140.7(3) . . . . ? C20 C19 C27 O14 17.6(4) . . . . ? C24 C19 C27 O14 -100.5(4) . . . . ? C18 C19 C27 O13 -45.4(4) . . . . ? C20 C19 C27 O13 -168.4(3) . . . . ? C24 C19 C27 O13 73.5(3) . . . . ? C22 C21 C28 O16 -114.8(4) . . . . ? C20 C21 C28 O16 5.8(5) . . . . ? C23 C21 C28 O16 125.8(4) . . . . ? C22 C21 C28 O15 63.9(4) . . . . ? C20 C21 C28 O15 -175.5(3) . . . . ? C23 C21 C28 O15 -55.5(4) . . . . ? N3 C34 N1 C29 59.8(4) . . . . ? N3 C34 N1 C33 -60.5(4) . . . . ? N2 C29 N1 C34 -60.2(4) . . . . ? N2 C29 N1 C33 59.7(4) . . . . ? N4 C33 N1 C34 61.2(4) . . . . ? N4 C33 N1 C29 -58.1(4) . . . . ? N1 C29 N2 C30 59.9(4) . . . . ? N1 C29 N2 C32 -59.3(4) . . . . ? N3 C30 N2 C29 -60.2(4) . . . . ? N3 C30 N2 C32 58.5(4) . . . . ? N4 C32 N2 C29 60.6(4) . . . . ? N4 C32 N2 C30 -58.6(4) . . . . ? N1 C34 N3 C31 59.0(4) . . . . ? N1 C34 N3 C30 -59.2(4) . . . . ? N4 C31 N3 C34 -60.1(5) . . . . ? N4 C31 N3 C30 58.1(4) . . . . ? N2 C30 N3 C34 59.8(4) . . . . ? N2 C30 N3 C31 -58.4(4) . . . . ? N1 C33 N4 C32 57.2(4) . . . . ? N1 C33 N4 C31 -59.3(4) . . . . ? N2 C32 N4 C33 -59.9(4) . . . . ? N2 C32 N4 C31 56.8(4) . . . . ? N3 C31 N4 C33 60.5(4) . . . . ? N3 C31 N4 C32 -57.0(4) . . . . ? N6 C35 N5 C39 60.0(4) . . . . ? N6 C35 N5 C40 -59.0(4) . . . . ? N8 C39 N5 C35 -59.0(4) . . . . ? N8 C39 N5 C40 60.3(4) . . . . ? N7 C40 N5 C35 58.7(4) . . . . ? N7 C40 N5 C39 -60.4(4) . . . . ? N5 C35 N6 C36 59.0(4) . . . . ? N5 C35 N6 C38 -59.5(4) . . . . ? N7 C36 N6 C35 -60.4(4) . . . . ? N7 C36 N6 C38 57.7(4) . . . . ? N8 C38 N6 C35 61.1(4) . . . . ? N8 C38 N6 C36 -57.8(4) . . . . ? N5 C40 N7 C36 -58.2(4) . . . . ? N5 C40 N7 C37 58.8(4) . . . . ? N6 C36 N7 C40 59.9(4) . . . . ? N6 C36 N7 C37 -57.6(4) . . . . ? N8 C37 N7 C40 -59.5(4) . . . . ? N8 C37 N7 C36 58.0(4) . . . . ? N5 C39 N8 C38 59.0(4) . . . . ? N5 C39 N8 C37 -59.3(4) . . . . ? N6 C38 N8 C39 -60.9(4) . . . . ? N6 C38 N8 C37 58.0(4) . . . . ? N7 C37 N8 C39 59.8(5) . . . . ? N7 C37 N8 C38 -58.6(4) . . . . ? 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 O3 H3 O10 0.94(4) 1.73(4) 2.673(3) 175(3) 4_566 O5 H5 O9 0.83(5) 1.74(5) 2.570(3) 177(6) 3_566 O7 H7 O2 0.90(4) 1.74(4) 2.634(3) 173(4) 3_667 O11 H11 N7 1.02(5) 1.74(5) 2.759(4) 172(4) 2 O13 H13 O1 0.97(4) 1.67(4) 2.627(3) 170(4) 4_565 O15 H15 N4 1.01(5) 1.75(5) 2.745(4) 166(4) 2_656 N1 H1 O1 0.89(4) 2.15(4) 2.847(4) 135(4) . N1 H1 O2 0.89(4) 1.98(4) 2.829(4) 159(4) . N5 H5A O9 0.93(5) 1.96(5) 2.840(4) 157(4) . N5 H5A O10 0.93(5) 2.08(4) 2.829(4) 136(4) . ###END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-09-23 at 07:50:31 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 9an274b_p smart2 data_FORM_II _database_code_depnum_ccdc_archive 'CCDC 845160' #TrackingRef '- Combined cif files.cif' _audit_creation_date 2009-09-23T07:50:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (adamantane-1-carboxylate-3,5,7-tricarboxylic acid).(hexamethylenetetraminium) Form II ; _chemical_formula_moiety 'C14 H15 O8, C6 H13 N4' _chemical_formula_sum 'C20 H28 N4 O8' _chemical_formula_weight 452.46 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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 13.9430(7) _cell_length_b 11.9137(6) _cell_length_c 25.0356(12) _cell_angle_alpha 90 _cell_angle_beta 91.074(4) _cell_angle_gamma 90 _cell_volume 4158.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2248 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 20.09 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.040 1.00 0.00 0.00 0.040 0.00 1.00 0.00 0.450 0.00 -1.00 -1.00 0.450 0.00 -1.00 4.00 0.190 3.00 0.00 1.00 0.050 -3.00 0.00 -1.00 0.050 -1.00 0.00 1.00 0.050 1.00 0.00 -1.00 0.050 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.99 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1157 _diffrn_reflns_av_unetI/netI 0.1547 _diffrn_reflns_number 27986 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 7736 _reflns_number_gt 3299 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0996P)^2^+2.1048P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0022(6) _refine_ls_number_reflns 7736 _refine_ls_number_parameters 602 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1858 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2506 _refine_ls_wR_factor_gt 0.1667 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.399 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.07 #----------------------------------------------------------------------------# # 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 C1 C 0.2142(3) 0.7213(4) 0.67952(16) 0.0264(10) Uani 1 1 d . . . C2 C 0.2057(3) 0.6178(4) 0.71644(17) 0.0291(11) Uani 1 1 d . . . H2A H 0.2225 0.5504 0.697 0.035 Uiso 1 1 calc R . . H2B H 0.2499 0.6254 0.7466 0.035 Uiso 1 1 calc R . . C3 C 0.1021(3) 0.6078(4) 0.73661(16) 0.0273(11) Uani 1 1 d . . . C4 C 0.0343(3) 0.5918(4) 0.68839(17) 0.0336(12) Uani 1 1 d . . . H4A H -0.0311 0.5834 0.7004 0.04 Uiso 1 1 calc R . . H4B H 0.0516 0.5243 0.6692 0.04 Uiso 1 1 calc R . . C5 C 0.0408(3) 0.6940(4) 0.65106(17) 0.0314(11) Uani 1 1 d . . . C6 C 0.0140(3) 0.8013(4) 0.68240(17) 0.0337(12) Uani 1 1 d . . . H6A H 0.0181 0.8661 0.6591 0.04 Uiso 1 1 calc R . . H6B H -0.0514 0.7953 0.6946 0.04 Uiso 1 1 calc R . . C7 C 0.0824(3) 0.8164(4) 0.73058(17) 0.0312(11) Uani 1 1 d . . . C8 C 0.0743(3) 0.7145(4) 0.76764(17) 0.0311(11) Uani 1 1 d . . . H8A H 0.0091 0.7077 0.7801 0.037 Uiso 1 1 calc R . . H8B H 0.1167 0.7238 0.7985 0.037 Uiso 1 1 calc R . . C9 C 0.1859(3) 0.8261(4) 0.71098(17) 0.0320(11) Uani 1 1 d . . . H9A H 0.1916 0.8918 0.6884 0.038 Uiso 1 1 calc R . . H9B H 0.2293 0.8353 0.7414 0.038 Uiso 1 1 calc R . . C10 C 0.1448(3) 0.7068(4) 0.63190(16) 0.0313(11) Uani 1 1 d . . . H10A H 0.1626 0.6409 0.6116 0.038 Uiso 1 1 calc R . . H10B H 0.1491 0.7716 0.6086 0.038 Uiso 1 1 calc R . . C11 C 0.3163(3) 0.7313(4) 0.65843(17) 0.0322(11) Uani 1 1 d . . . C12 C 0.1005(3) 0.5020(4) 0.77047(18) 0.0322(11) Uani 1 1 d . . . C13 C -0.0228(3) 0.6820(5) 0.60169(19) 0.0366(12) Uani 1 1 d . . . C14 C 0.0577(4) 0.9231(4) 0.76065(19) 0.0351(12) Uani 1 1 d . . . O1 O 0.3745(2) 0.6517(3) 0.66333(15) 0.0518(10) Uani 1 1 d . . . O2 O 0.3398(2) 0.8219(3) 0.63526(12) 0.0388(9) Uani 1 1 d . . . O3 O 0.1332(3) 0.5171(3) 0.82037(13) 0.0425(9) Uani 1 1 d . . . H3 H 0.135(4) 0.446(5) 0.835(2) 0.064 Uiso 1 1 d . . . O4 O 0.0772(3) 0.4102(3) 0.75383(14) 0.0519(10) Uani 1 1 d . . . O5 O -0.0454(3) 0.5770(3) 0.59115(16) 0.0689(14) Uani 1 1 d . . . H5 H -0.075(5) 0.566(6) 0.557(3) 0.103 Uiso 1 1 d . . . O6 O -0.0507(3) 0.7591(3) 0.57434(15) 0.0650(12) Uani 1 1 d . . . O7 O 0.1192(3) 0.9425(3) 0.80105(14) 0.0464(10) Uani 1 1 d . . . H7 H 0.113(4) 1.020(5) 0.814(2) 0.07 Uiso 1 1 d . . . O8 O -0.0086(3) 0.9850(4) 0.75044(16) 0.0670(12) Uani 1 1 d . . . C15 C 0.2697(3) 0.6060(4) 0.47471(17) 0.0292(11) Uani 1 1 d . . . C16 C 0.2322(3) 0.6025(4) 0.41668(16) 0.0310(11) Uani 1 1 d . . . H16A H 0.1633 0.6139 0.416 0.037 Uiso 1 1 calc R . . H16B H 0.2451 0.5292 0.4015 0.037 Uiso 1 1 calc R . . C17 C 0.2802(3) 0.6936(4) 0.38285(17) 0.0311(11) Uani 1 1 d . . . C18 C 0.3891(3) 0.6752(4) 0.38319(17) 0.0326(11) Uani 1 1 d . . . H18A H 0.4194 0.7328 0.3619 0.039 Uiso 1 1 calc R . . H18B H 0.4036 0.6028 0.3676 0.039 Uiso 1 1 calc R . . C19 C 0.4285(3) 0.6802(4) 0.44086(17) 0.0293(11) Uani 1 1 d . . . C20 C 0.4062(3) 0.7956(4) 0.4653(2) 0.0367(12) Uani 1 1 d . . . H20A H 0.4311 0.7988 0.5017 0.044 Uiso 1 1 calc R . . H20B H 0.4371 0.854 0.4449 0.044 Uiso 1 1 calc R . . C21 C 0.2973(3) 0.8151(4) 0.46489(18) 0.0320(11) Uani 1 1 d . . . C22 C 0.2581(4) 0.8096(4) 0.40678(18) 0.0380(12) Uani 1 1 d . . . H22A H 0.1894 0.8222 0.4062 0.046 Uiso 1 1 calc R . . H22B H 0.2878 0.8678 0.3856 0.046 Uiso 1 1 calc R . . C23 C 0.2491(3) 0.7220(4) 0.49821(18) 0.0335(11) Uani 1 1 d . . . H23A H 0.2732 0.7252 0.5348 0.04 Uiso 1 1 calc R . . H23B H 0.1804 0.7345 0.4985 0.04 Uiso 1 1 calc R . . C24 C 0.3794(3) 0.5880(4) 0.47496(17) 0.0292(11) Uani 1 1 d . . . H24A H 0.3938 0.5145 0.4605 0.035 Uiso 1 1 calc R . . H24B H 0.4043 0.591 0.5114 0.035 Uiso 1 1 calc R . . C25 C 0.2209(3) 0.5175(4) 0.50884(18) 0.0310(11) Uani 1 1 d . . . C26 C 0.2419(4) 0.6878(5) 0.32571(18) 0.0382(12) Uani 1 1 d . . . C27 C 0.5356(3) 0.6572(4) 0.4431(2) 0.0371(12) Uani 1 1 d . . . C28 C 0.2741(4) 0.9272(4) 0.4900(2) 0.0398(13) Uani 1 1 d . . . O9 O 0.1433(3) 0.4737(3) 0.49351(13) 0.0529(11) Uani 1 1 d . . . O10 O 0.2587(2) 0.4926(3) 0.55407(12) 0.0364(8) Uani 1 1 d . . . O11 O 0.2743(3) 0.7665(4) 0.29424(15) 0.0740(14) Uani 1 1 d . . . H11 H 0.235(5) 0.745(6) 0.259(3) 0.111 Uiso 1 1 d . . . O12 O 0.1868(4) 0.6173(4) 0.30946(15) 0.0955(19) Uani 1 1 d . . . O13 O 0.5601(2) 0.5618(3) 0.41952(13) 0.0449(9) Uani 1 1 d . . . H13 H 0.625(4) 0.541(5) 0.431(2) 0.067 Uiso 1 1 d . . . O14 O 0.5936(3) 0.7170(4) 0.4659(2) 0.0829(15) Uani 1 1 d . . . O15 O 0.1807(3) 0.9492(4) 0.48955(18) 0.0661(13) Uani 1 1 d . . . H15 H 0.172(5) 1.017(6) 0.510(3) 0.099 Uiso 1 1 d . . . O16 O 0.3312(3) 0.9911(3) 0.50966(17) 0.0611(11) Uani 1 1 d . . . C29 C 0.5735(4) 0.8904(6) 0.6238(2) 0.0614(17) Uani 1 1 d . . . H29A H 0.5448 0.9028 0.5887 0.074 Uiso 1 1 calc R . . H29B H 0.5515 0.9492 0.6474 0.074 Uiso 1 1 calc R . . C30 C 0.7058(4) 0.8066(5) 0.5833(2) 0.0517(15) Uani 1 1 d . . . H30A H 0.7749 0.8104 0.5796 0.062 Uiso 1 1 calc R . . H30B H 0.6764 0.8198 0.5485 0.062 Uiso 1 1 calc R . . C31 C 0.7223(4) 0.6747(5) 0.6550(2) 0.0557(16) Uani 1 1 d . . . H31A H 0.7916 0.6758 0.6524 0.067 Uiso 1 1 calc R . . H31B H 0.7035 0.6012 0.6677 0.067 Uiso 1 1 calc R . . C32 C 0.7178(4) 0.8734(5) 0.6734(2) 0.0506(15) Uani 1 1 d . . . H32A H 0.6961 0.9304 0.6981 0.061 Uiso 1 1 calc R . . H32B H 0.7871 0.879 0.6714 0.061 Uiso 1 1 calc R . . C33 C 0.5881(4) 0.7560(5) 0.6982(2) 0.0521(15) Uani 1 1 d . . . H33A H 0.5666 0.8115 0.7236 0.063 Uiso 1 1 calc R . . H33B H 0.5693 0.6824 0.7109 0.063 Uiso 1 1 calc R . . C34 C 0.5762(4) 0.6889(5) 0.6056(2) 0.0586(17) Uani 1 1 d . . . H34A H 0.5569 0.6151 0.6177 0.07 Uiso 1 1 calc R . . H34B H 0.5471 0.702 0.5706 0.07 Uiso 1 1 calc R . . N1 N 0.5430(3) 0.7779(5) 0.64469(18) 0.0546(14) Uani 1 1 d . . . H1 H 0.472(5) 0.769(5) 0.647(2) 0.082 Uiso 1 1 d . . . N2 N 0.6751(3) 0.8945(4) 0.62049(17) 0.0488(12) Uani 1 1 d . . . N3 N 0.6793(3) 0.6940(4) 0.60211(16) 0.0490(12) Uani 1 1 d . . . N4 N 0.6918(3) 0.7614(4) 0.69374(16) 0.0443(11) Uani 1 1 d . . . C35 C 0.1899(4) 0.2740(5) 0.6372(2) 0.0549(16) Uani 1 1 d . . . H35A H 0.259 0.2655 0.6358 0.066 Uiso 1 1 calc R . . H35B H 0.1756 0.3297 0.6641 0.066 Uiso 1 1 calc R . . C36 C 0.1696(5) 0.0857(5) 0.6095(2) 0.0664(18) Uani 1 1 d . . . H36A H 0.2387 0.077 0.6081 0.08 Uiso 1 1 calc R . . H36B H 0.1424 0.0137 0.619 0.08 Uiso 1 1 calc R . . C37 C 0.0276(4) 0.1344(5) 0.5597(2) 0.0520(15) Uani 1 1 d . . . H37A H 0.0026 0.1579 0.5251 0.062 Uiso 1 1 calc R . . H37B H -0.002 0.0633 0.5685 0.062 Uiso 1 1 calc R . . C38 C 0.0414(5) 0.1834(6) 0.6521(2) 0.0653(18) Uani 1 1 d . . . H38A H 0.0117 0.1135 0.6628 0.078 Uiso 1 1 calc R . . H38B H 0.026 0.24 0.6784 0.078 Uiso 1 1 calc R . . C39 C 0.0445(4) 0.3237(5) 0.5857(2) 0.0458(14) Uani 1 1 d . . . H39A H 0.0276 0.3799 0.612 0.055 Uiso 1 1 calc R . . H39B H 0.0199 0.3481 0.5511 0.055 Uiso 1 1 calc R . . C40 C 0.1765(4) 0.2250(4) 0.54244(18) 0.0380(12) Uani 1 1 d . . . H40A H 0.153 0.249 0.5076 0.046 Uiso 1 1 calc R . . H40B H 0.2456 0.2165 0.5409 0.046 Uiso 1 1 calc R . . N5 N 0.1516(3) 0.3118(4) 0.58403(16) 0.0409(11) Uani 1 1 d . . . H5A H 0.179(4) 0.369(5) 0.576(2) 0.061 Uiso 1 1 d . . . N6 N 0.1466(4) 0.1683(5) 0.65099(18) 0.0644(15) Uani 1 1 d . . . N7 N 0.1327(3) 0.1188(3) 0.55660(16) 0.0397(11) Uani 1 1 d . . . N8 N 0.0022(3) 0.2176(4) 0.59955(17) 0.0482(12) 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 C1 0.026(2) 0.020(3) 0.033(2) 0.0000(19) 0.0057(19) -0.003(2) C2 0.023(2) 0.029(3) 0.036(2) 0.002(2) 0.0029(19) -0.003(2) C3 0.021(2) 0.031(3) 0.030(2) 0.001(2) 0.0020(19) -0.006(2) C4 0.029(3) 0.037(3) 0.035(3) 0.001(2) -0.001(2) -0.003(2) C5 0.028(3) 0.033(3) 0.033(2) 0.001(2) 0.000(2) 0.000(2) C6 0.033(3) 0.030(3) 0.038(3) 0.005(2) -0.001(2) 0.000(2) C7 0.031(3) 0.029(3) 0.034(2) -0.004(2) 0.000(2) -0.002(2) C8 0.031(3) 0.032(3) 0.030(2) 0.000(2) 0.002(2) -0.002(2) C9 0.034(3) 0.029(3) 0.033(2) 0.002(2) 0.001(2) -0.001(2) C10 0.032(3) 0.033(3) 0.029(2) 0.000(2) 0.002(2) -0.002(2) C11 0.032(3) 0.035(3) 0.030(2) -0.001(2) 0.001(2) -0.007(2) C12 0.029(3) 0.030(3) 0.038(3) 0.007(2) 0.004(2) -0.003(2) C13 0.030(3) 0.040(3) 0.040(3) 0.001(3) 0.000(2) -0.001(3) C14 0.039(3) 0.026(3) 0.041(3) -0.005(2) 0.007(2) -0.002(2) O1 0.030(2) 0.048(3) 0.078(3) 0.022(2) 0.0146(18) 0.0081(18) O2 0.042(2) 0.034(2) 0.0409(19) -0.0046(16) 0.0128(15) -0.0095(17) O3 0.055(2) 0.033(2) 0.039(2) 0.0052(16) -0.0045(16) -0.0006(18) O4 0.067(3) 0.034(2) 0.054(2) 0.0000(18) -0.0128(19) -0.016(2) O5 0.100(4) 0.048(3) 0.057(2) -0.001(2) -0.044(2) -0.012(2) O6 0.084(3) 0.049(3) 0.061(2) 0.011(2) -0.037(2) -0.003(2) O7 0.048(2) 0.039(2) 0.052(2) -0.0148(18) -0.0004(18) 0.0027(19) O8 0.067(3) 0.055(3) 0.078(3) -0.022(2) -0.015(2) 0.032(2) C15 0.027(3) 0.031(3) 0.031(2) -0.004(2) 0.0047(19) -0.003(2) C16 0.024(2) 0.034(3) 0.035(3) 0.002(2) -0.001(2) 0.000(2) C17 0.032(3) 0.030(3) 0.031(2) -0.002(2) 0.000(2) -0.001(2) C18 0.032(3) 0.034(3) 0.031(2) 0.001(2) 0.002(2) 0.000(2) C19 0.027(3) 0.028(3) 0.033(2) 0.004(2) 0.000(2) -0.003(2) C20 0.031(3) 0.030(3) 0.048(3) 0.000(2) -0.001(2) -0.002(2) C21 0.033(3) 0.024(3) 0.039(3) -0.003(2) 0.000(2) -0.001(2) C22 0.038(3) 0.033(3) 0.043(3) -0.001(2) 0.003(2) 0.002(2) C23 0.030(3) 0.033(3) 0.038(3) -0.002(2) 0.006(2) 0.000(2) C24 0.025(2) 0.031(3) 0.031(2) 0.003(2) -0.0007(19) -0.001(2) C25 0.030(3) 0.030(3) 0.033(3) -0.008(2) 0.003(2) 0.002(2) C26 0.041(3) 0.041(3) 0.032(3) 0.004(2) 0.000(2) -0.003(3) C27 0.030(3) 0.034(3) 0.048(3) 0.002(2) 0.006(2) -0.003(2) C28 0.040(3) 0.033(3) 0.046(3) -0.002(2) 0.005(2) 0.003(3) O9 0.045(2) 0.067(3) 0.046(2) 0.0120(19) -0.0126(17) -0.031(2) O10 0.0302(18) 0.045(2) 0.0342(18) 0.0069(15) -0.0025(14) -0.0014(16) O11 0.102(4) 0.077(3) 0.043(2) 0.021(2) -0.017(2) -0.039(3) O12 0.132(4) 0.107(4) 0.046(2) 0.018(2) -0.030(3) -0.075(4) O13 0.0288(19) 0.056(3) 0.050(2) -0.0060(19) -0.0010(16) 0.0071(18) O14 0.035(2) 0.066(3) 0.148(4) -0.040(3) -0.009(3) -0.006(2) O15 0.040(2) 0.050(3) 0.109(3) -0.039(2) 0.001(2) 0.012(2) O16 0.057(3) 0.038(2) 0.089(3) -0.025(2) -0.002(2) -0.008(2) C29 0.061(4) 0.062(5) 0.062(4) -0.005(3) 0.001(3) 0.022(3) C30 0.045(3) 0.064(4) 0.047(3) 0.003(3) 0.015(3) -0.001(3) C31 0.062(4) 0.058(4) 0.048(3) -0.003(3) 0.007(3) 0.022(3) C32 0.043(3) 0.052(4) 0.057(3) -0.013(3) -0.004(3) -0.006(3) C33 0.052(4) 0.060(4) 0.045(3) -0.011(3) 0.016(3) -0.013(3) C34 0.062(4) 0.061(4) 0.053(3) -0.018(3) 0.002(3) -0.013(3) N1 0.027(3) 0.079(4) 0.059(3) -0.017(3) 0.009(2) -0.013(3) N2 0.046(3) 0.047(3) 0.054(3) 0.000(2) 0.004(2) -0.005(2) N3 0.051(3) 0.056(3) 0.040(2) -0.009(2) 0.004(2) 0.007(2) N4 0.048(3) 0.046(3) 0.039(2) -0.009(2) 0.0035(19) 0.002(2) C35 0.055(4) 0.071(5) 0.038(3) -0.006(3) -0.013(3) -0.010(3) C36 0.081(5) 0.046(4) 0.072(4) 0.017(3) -0.006(4) 0.012(4) C37 0.046(3) 0.044(4) 0.066(4) -0.007(3) 0.007(3) -0.013(3) C38 0.082(5) 0.064(5) 0.052(4) 0.013(3) 0.027(3) -0.014(4) C39 0.047(3) 0.036(3) 0.055(3) -0.005(3) 0.006(3) 0.006(3) C40 0.034(3) 0.042(3) 0.038(3) 0.002(2) 0.004(2) -0.001(2) N5 0.048(3) 0.037(3) 0.038(2) 0.000(2) 0.004(2) -0.010(2) N6 0.074(4) 0.077(4) 0.042(3) 0.018(3) 0.001(2) 0.002(3) N7 0.036(2) 0.031(3) 0.052(3) 0.002(2) 0.000(2) 0.004(2) N8 0.037(3) 0.050(3) 0.058(3) -0.005(2) 0.014(2) -0.005(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C10 1.531(6) . ? C1 C9 1.532(6) . ? C1 C11 1.533(6) . ? C1 C2 1.546(6) . ? C2 C3 1.544(6) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C12 1.520(6) . ? C3 C4 1.531(6) . ? C3 C8 1.542(6) . ? C4 C5 1.538(6) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C13 1.515(6) . ? C5 C10 1.544(6) . ? C5 C6 1.549(6) . ? C6 C7 1.534(6) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 C14 1.520(7) . ? C7 C8 1.534(6) . ? C7 C9 1.537(6) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 O1 1.252(6) . ? C11 O2 1.272(5) . ? C12 O4 1.212(6) . ? C12 O3 1.334(5) . ? C13 O6 1.206(6) . ? C13 O5 1.315(6) . ? C14 O8 1.207(6) . ? C14 O7 1.334(6) . ? O3 H3 0.92(6) . ? O5 H5 0.96(7) . ? O7 H7 0.98(6) . ? C15 C25 1.526(6) . ? C15 C23 1.531(6) . ? C15 C16 1.535(6) . ? C15 C24 1.545(6) . ? C16 C17 1.538(6) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C26 1.519(6) . ? C17 C18 1.534(6) . ? C17 C22 1.540(7) . ? C18 C19 1.536(6) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C19 C27 1.518(6) . ? C19 C20 1.539(7) . ? C19 C24 1.558(6) . ? C20 C21 1.536(6) . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C21 C28 1.513(7) . ? C21 C22 1.546(6) . ? C21 C23 1.548(6) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? C25 O9 1.255(5) . ? C25 O10 1.275(5) . ? C26 O12 1.204(6) . ? C26 O11 1.310(6) . ? C27 O14 1.213(6) . ? C27 O13 1.328(6) . ? C28 O16 1.201(6) . ? C28 O15 1.329(6) . ? O11 H11 1.07(8) . ? O13 H13 0.97(6) . ? O15 H15 0.96(7) . ? C29 N2 1.422(7) . ? C29 N1 1.504(8) . ? C29 H29A 0.97 . ? C29 H29B 0.97 . ? C30 N2 1.469(7) . ? C30 N3 1.471(7) . ? C30 H30A 0.97 . ? C30 H30B 0.97 . ? C31 N3 1.461(6) . ? C31 N4 1.485(7) . ? C31 H31A 0.97 . ? C31 H31B 0.97 . ? C32 N2 1.463(6) . ? C32 N4 1.476(7) . ? C32 H32A 0.97 . ? C32 H32B 0.97 . ? C33 N4 1.455(7) . ? C33 N1 1.492(7) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 N3 1.442(7) . ? C34 N1 1.521(7) . ? C34 H34A 0.97 . ? C34 H34B 0.97 . ? N1 H1 1.00(7) . ? C35 N6 1.441(8) . ? C35 N5 1.493(6) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 N7 1.467(7) . ? C36 N6 1.469(8) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 N8 1.454(7) . ? C37 N7 1.480(6) . ? C37 H37A 0.97 . ? C37 H37B 0.97 . ? C38 N8 1.473(7) . ? C38 N6 1.478(8) . ? C38 H38A 0.97 . ? C38 H38B 0.97 . ? C39 N8 1.440(7) . ? C39 N5 1.501(7) . ? C39 H39A 0.97 . ? C39 H39B 0.97 . ? C40 N7 1.452(6) . ? C40 N5 1.512(6) . ? C40 H40A 0.97 . ? C40 H40B 0.97 . ? N5 H5A 0.80(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 C10 C1 C9 109.1(4) . . ? C10 C1 C11 108.5(3) . . ? C9 C1 C11 111.3(4) . . ? C10 C1 C2 108.8(4) . . ? C9 C1 C2 108.6(3) . . ? C11 C1 C2 110.5(4) . . ? C3 C2 C1 109.8(4) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C12 C3 C4 108.7(4) . . ? C12 C3 C8 113.3(4) . . ? C4 C3 C8 110.0(4) . . ? C12 C3 C2 105.7(4) . . ? C4 C3 C2 108.6(3) . . ? C8 C3 C2 110.3(4) . . ? C3 C4 C5 109.7(4) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C13 C5 C4 112.4(4) . . ? C13 C5 C10 107.1(4) . . ? C4 C5 C10 109.5(4) . . ? C13 C5 C6 110.4(4) . . ? C4 C5 C6 109.1(4) . . ? C10 C5 C6 108.2(4) . . ? C7 C6 C5 110.1(4) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? C14 C7 C8 110.1(4) . . ? C14 C7 C6 110.2(4) . . ? C8 C7 C6 109.3(4) . . ? C14 C7 C9 108.6(4) . . ? C8 C7 C9 109.4(4) . . ? C6 C7 C9 109.3(4) . . ? C7 C8 C3 109.0(3) . . ? C7 C8 H8A 109.9 . . ? C3 C8 H8A 109.9 . . ? C7 C8 H8B 109.9 . . ? C3 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C1 C9 C7 110.8(4) . . ? C1 C9 H9A 109.5 . . ? C7 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C1 C10 C5 110.6(3) . . ? C1 C10 H10A 109.5 . . ? C5 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 C11 O2 121.0(4) . . ? O1 C11 C1 120.8(4) . . ? O2 C11 C1 118.1(4) . . ? O4 C12 O3 121.9(4) . . ? O4 C12 C3 124.3(4) . . ? O3 C12 C3 113.7(4) . . ? O6 C13 O5 122.5(5) . . ? O6 C13 C5 124.7(5) . . ? O5 C13 C5 112.8(4) . . ? O8 C14 O7 122.3(4) . . ? O8 C14 C7 125.9(5) . . ? O7 C14 C7 111.8(4) . . ? C12 O3 H3 105(3) . . ? C13 O5 H5 114(4) . . ? C14 O7 H7 111(3) . . ? C25 C15 C23 108.6(3) . . ? C25 C15 C16 111.3(4) . . ? C23 C15 C16 109.0(4) . . ? C25 C15 C24 110.7(4) . . ? C23 C15 C24 108.5(4) . . ? C16 C15 C24 108.7(3) . . ? C15 C16 C17 110.9(4) . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108 . . ? C26 C17 C18 109.2(4) . . ? C26 C17 C16 109.7(4) . . ? C18 C17 C16 109.8(4) . . ? C26 C17 C22 109.7(4) . . ? C18 C17 C22 109.3(4) . . ? C16 C17 C22 109.1(4) . . ? C17 C18 C19 109.7(4) . . ? C17 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? C17 C18 H18B 109.7 . . ? C19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C27 C19 C18 111.2(4) . . ? C27 C19 C20 110.6(4) . . ? C18 C19 C20 109.7(4) . . ? C27 C19 C24 107.2(4) . . ? C18 C19 C24 109.6(4) . . ? C20 C19 C24 108.5(4) . . ? C21 C20 C19 109.9(4) . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C28 C21 C20 110.5(4) . . ? C28 C21 C22 110.7(4) . . ? C20 C21 C22 109.4(4) . . ? C28 C21 C23 108.0(4) . . ? C20 C21 C23 109.1(4) . . ? C22 C21 C23 109.1(4) . . ? C17 C22 C21 109.5(4) . . ? C17 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? C17 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? C15 C23 C21 110.6(4) . . ? C15 C23 H23A 109.5 . . ? C21 C23 H23A 109.5 . . ? C15 C23 H23B 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C15 C24 C19 110.2(4) . . ? C15 C24 H24A 109.6 . . ? C19 C24 H24A 109.6 . . ? C15 C24 H24B 109.6 . . ? C19 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? O9 C25 O10 121.0(4) . . ? O9 C25 C15 120.5(4) . . ? O10 C25 C15 118.5(4) . . ? O12 C26 O11 121.4(5) . . ? O12 C26 C17 124.1(5) . . ? O11 C26 C17 114.5(5) . . ? O14 C27 O13 122.5(5) . . ? O14 C27 C19 123.9(5) . . ? O13 C27 C19 113.5(4) . . ? O16 C28 O15 121.4(5) . . ? O16 C28 C21 125.8(5) . . ? O15 C28 C21 112.8(5) . . ? C26 O11 H11 99(4) . . ? C27 O13 H13 109(3) . . ? C28 O15 H15 107(4) . . ? N2 C29 N1 109.8(5) . . ? N2 C29 H29A 109.7 . . ? N1 C29 H29A 109.7 . . ? N2 C29 H29B 109.7 . . ? N1 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? N2 C30 N3 111.7(4) . . ? N2 C30 H30A 109.3 . . ? N3 C30 H30A 109.3 . . ? N2 C30 H30B 109.3 . . ? N3 C30 H30B 109.3 . . ? H30A C30 H30B 107.9 . . ? N3 C31 N4 111.4(4) . . ? N3 C31 H31A 109.3 . . ? N4 C31 H31A 109.3 . . ? N3 C31 H31B 109.3 . . ? N4 C31 H31B 109.3 . . ? H31A C31 H31B 108 . . ? N2 C32 N4 111.6(4) . . ? N2 C32 H32A 109.3 . . ? N4 C32 H32A 109.3 . . ? N2 C32 H32B 109.3 . . ? N4 C32 H32B 109.3 . . ? H32A C32 H32B 108 . . ? N4 C33 N1 109.0(4) . . ? N4 C33 H33A 109.9 . . ? N1 C33 H33A 109.9 . . ? N4 C33 H33B 109.9 . . ? N1 C33 H33B 109.9 . . ? H33A C33 H33B 108.3 . . ? N3 C34 N1 109.0(4) . . ? N3 C34 H34A 109.9 . . ? N1 C34 H34A 109.9 . . ? N3 C34 H34B 109.9 . . ? N1 C34 H34B 109.9 . . ? H34A C34 H34B 108.3 . . ? C33 N1 C29 110.6(4) . . ? C33 N1 C34 109.1(5) . . ? C29 N1 C34 107.8(4) . . ? C33 N1 H1 109(3) . . ? C29 N1 H1 114(4) . . ? C34 N1 H1 106(4) . . ? C29 N2 C32 109.3(4) . . ? C29 N2 C30 108.4(4) . . ? C32 N2 C30 109.4(4) . . ? C34 N3 C31 109.4(4) . . ? C34 N3 C30 108.4(5) . . ? C31 N3 C30 109.3(4) . . ? C33 N4 C32 108.5(4) . . ? C33 N4 C31 108.4(4) . . ? C32 N4 C31 109.2(4) . . ? N6 C35 N5 109.5(4) . . ? N6 C35 H35A 109.8 . . ? N5 C35 H35A 109.8 . . ? N6 C35 H35B 109.8 . . ? N5 C35 H35B 109.8 . . ? H35A C35 H35B 108.2 . . ? N7 C36 N6 112.4(5) . . ? N7 C36 H36A 109.1 . . ? N6 C36 H36A 109.1 . . ? N7 C36 H36B 109.1 . . ? N6 C36 H36B 109.1 . . ? H36A C36 H36B 107.9 . . ? N8 C37 N7 112.1(4) . . ? N8 C37 H37A 109.2 . . ? N7 C37 H37A 109.2 . . ? N8 C37 H37B 109.2 . . ? N7 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? N8 C38 N6 111.6(4) . . ? N8 C38 H38A 109.3 . . ? N6 C38 H38A 109.3 . . ? N8 C38 H38B 109.3 . . ? N6 C38 H38B 109.3 . . ? H38A C38 H38B 108 . . ? N8 C39 N5 109.6(4) . . ? N8 C39 H39A 109.8 . . ? N5 C39 H39A 109.8 . . ? N8 C39 H39B 109.8 . . ? N5 C39 H39B 109.8 . . ? H39A C39 H39B 108.2 . . ? N7 C40 N5 108.9(4) . . ? N7 C40 H40A 109.9 . . ? N5 C40 H40A 109.9 . . ? N7 C40 H40B 109.9 . . ? N5 C40 H40B 109.9 . . ? H40A C40 H40B 108.3 . . ? C35 N5 C39 110.0(4) . . ? C35 N5 C40 108.9(4) . . ? C39 N5 C40 109.0(4) . . ? C35 N5 H5A 108(4) . . ? C39 N5 H5A 113(4) . . ? C40 N5 H5A 107(4) . . ? C35 N6 C36 108.5(5) . . ? C35 N6 C38 108.5(5) . . ? C36 N6 C38 108.9(5) . . ? C40 N7 C36 108.2(4) . . ? C40 N7 C37 108.9(4) . . ? C36 N7 C37 108.5(4) . . ? C39 N8 C37 109.1(4) . . ? C39 N8 C38 108.1(4) . . ? C37 N8 C38 109.4(5) . . ? 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 C10 C1 C2 C3 -60.1(4) . . . . ? C9 C1 C2 C3 58.6(4) . . . . ? C11 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C12 177.9(4) . . . . ? C1 C2 C3 C4 61.3(5) . . . . ? C1 C2 C3 C8 -59.3(4) . . . . ? C12 C3 C4 C5 -175.4(4) . . . . ? C8 C3 C4 C5 59.9(5) . . . . ? C2 C3 C4 C5 -60.9(5) . . . . ? C3 C4 C5 C13 178.5(4) . . . . ? C3 C4 C5 C10 59.5(5) . . . . ? C3 C4 C5 C6 -58.7(5) . . . . ? C13 C5 C6 C7 -176.8(4) . . . . ? C4 C5 C6 C7 59.2(5) . . . . ? C10 C5 C6 C7 -59.8(5) . . . . ? C5 C6 C7 C14 178.7(4) . . . . ? C5 C6 C7 C8 -60.3(5) . . . . ? C5 C6 C7 C9 59.5(5) . . . . ? C14 C7 C8 C3 -178.6(4) . . . . ? C6 C7 C8 C3 60.3(5) . . . . ? C9 C7 C8 C3 -59.4(5) . . . . ? C12 C3 C8 C7 177.6(4) . . . . ? C4 C3 C8 C7 -60.4(5) . . . . ? C2 C3 C8 C7 59.4(4) . . . . ? C10 C1 C9 C7 58.7(5) . . . . ? C11 C1 C9 C7 178.4(4) . . . . ? C2 C1 C9 C7 -59.8(5) . . . . ? C14 C7 C9 C1 -179.1(4) . . . . ? C8 C7 C9 C1 60.8(5) . . . . ? C6 C7 C9 C1 -58.9(5) . . . . ? C9 C1 C10 C5 -59.7(5) . . . . ? C11 C1 C10 C5 178.9(4) . . . . ? C2 C1 C10 C5 58.7(5) . . . . ? C13 C5 C10 C1 179.2(4) . . . . ? C4 C5 C10 C1 -58.7(5) . . . . ? C6 C5 C10 C1 60.1(5) . . . . ? C10 C1 C11 O1 -106.2(5) . . . . ? C9 C1 C11 O1 133.7(5) . . . . ? C2 C1 C11 O1 13.0(6) . . . . ? C10 C1 C11 O2 72.9(5) . . . . ? C9 C1 C11 O2 -47.2(5) . . . . ? C2 C1 C11 O2 -167.9(4) . . . . ? C4 C3 C12 O4 22.8(6) . . . . ? C8 C3 C12 O4 145.5(5) . . . . ? C2 C3 C12 O4 -93.7(5) . . . . ? C4 C3 C12 O3 -161.3(4) . . . . ? C8 C3 C12 O3 -38.6(5) . . . . ? C2 C3 C12 O3 82.2(5) . . . . ? C4 C5 C13 O6 158.8(5) . . . . ? C10 C5 C13 O6 -80.9(6) . . . . ? C6 C5 C13 O6 36.7(7) . . . . ? C4 C5 C13 O5 -21.2(6) . . . . ? C10 C5 C13 O5 99.1(5) . . . . ? C6 C5 C13 O5 -143.2(4) . . . . ? C8 C7 C14 O8 -117.1(6) . . . . ? C6 C7 C14 O8 3.5(7) . . . . ? C9 C7 C14 O8 123.2(5) . . . . ? C8 C7 C14 O7 63.0(5) . . . . ? C6 C7 C14 O7 -176.4(4) . . . . ? C9 C7 C14 O7 -56.7(5) . . . . ? C25 C15 C16 C17 178.8(4) . . . . ? C23 C15 C16 C17 59.0(5) . . . . ? C24 C15 C16 C17 -59.0(5) . . . . ? C15 C16 C17 C26 179.9(4) . . . . ? C15 C16 C17 C18 59.8(5) . . . . ? C15 C16 C17 C22 -59.9(5) . . . . ? C26 C17 C18 C19 -179.7(4) . . . . ? C16 C17 C18 C19 -59.3(5) . . . . ? C22 C17 C18 C19 60.3(5) . . . . ? C17 C18 C19 C27 177.5(4) . . . . ? C17 C18 C19 C20 -59.8(5) . . . . ? C17 C18 C19 C24 59.2(5) . . . . ? C27 C19 C20 C21 -177.6(4) . . . . ? C18 C19 C20 C21 59.4(5) . . . . ? C24 C19 C20 C21 -60.3(5) . . . . ? C19 C20 C21 C28 178.7(4) . . . . ? C19 C20 C21 C22 -59.2(5) . . . . ? C19 C20 C21 C23 60.1(5) . . . . ? C26 C17 C22 C21 -180.0(4) . . . . ? C18 C17 C22 C21 -60.2(5) . . . . ? C16 C17 C22 C21 59.8(5) . . . . ? C28 C21 C22 C17 -178.4(4) . . . . ? C20 C21 C22 C17 59.7(5) . . . . ? C23 C21 C22 C17 -59.6(5) . . . . ? C25 C15 C23 C21 180.0(4) . . . . ? C16 C15 C23 C21 -58.6(5) . . . . ? C24 C15 C23 C21 59.6(5) . . . . ? C28 C21 C23 C15 179.8(4) . . . . ? C20 C21 C23 C15 -60.0(5) . . . . ? C22 C21 C23 C15 59.4(5) . . . . ? C25 C15 C24 C19 -178.9(3) . . . . ? C23 C15 C24 C19 -59.8(5) . . . . ? C16 C15 C24 C19 58.6(5) . . . . ? C27 C19 C24 C15 179.9(4) . . . . ? C18 C19 C24 C15 -59.4(5) . . . . ? C20 C19 C24 C15 60.4(5) . . . . ? C23 C15 C25 O9 101.6(5) . . . . ? C16 C15 C25 O9 -18.4(6) . . . . ? C24 C15 C25 O9 -139.4(4) . . . . ? C23 C15 C25 O10 -75.6(5) . . . . ? C16 C15 C25 O10 164.3(4) . . . . ? C24 C15 C25 O10 43.4(5) . . . . ? C18 C17 C26 O12 116.0(6) . . . . ? C16 C17 C26 O12 -4.3(7) . . . . ? C22 C17 C26 O12 -124.2(6) . . . . ? C18 C17 C26 O11 -63.4(6) . . . . ? C16 C17 C26 O11 176.2(4) . . . . ? C22 C17 C26 O11 56.4(6) . . . . ? C18 C19 C27 O14 129.0(6) . . . . ? C20 C19 C27 O14 6.9(7) . . . . ? C24 C19 C27 O14 -111.2(6) . . . . ? C18 C19 C27 O13 -53.9(5) . . . . ? C20 C19 C27 O13 -176.0(4) . . . . ? C24 C19 C27 O13 65.9(5) . . . . ? C20 C21 C28 O16 -2.9(7) . . . . ? C22 C21 C28 O16 -124.2(6) . . . . ? C23 C21 C28 O16 116.4(6) . . . . ? C20 C21 C28 O15 178.6(4) . . . . ? C22 C21 C28 O15 57.3(6) . . . . ? C23 C21 C28 O15 -62.1(5) . . . . ? N4 C33 N1 C29 -58.0(6) . . . . ? N4 C33 N1 C34 60.4(6) . . . . ? N2 C29 N1 C33 58.1(6) . . . . ? N2 C29 N1 C34 -61.1(6) . . . . ? N3 C34 N1 C33 -59.9(6) . . . . ? N3 C34 N1 C29 60.3(6) . . . . ? N1 C29 N2 C32 -58.2(6) . . . . ? N1 C29 N2 C30 60.9(6) . . . . ? N4 C32 N2 C29 61.1(6) . . . . ? N4 C32 N2 C30 -57.4(6) . . . . ? N3 C30 N2 C29 -61.4(6) . . . . ? N3 C30 N2 C32 57.8(6) . . . . ? N1 C34 N3 C31 59.2(6) . . . . ? N1 C34 N3 C30 -59.9(6) . . . . ? N4 C31 N3 C34 -60.8(6) . . . . ? N4 C31 N3 C30 57.7(6) . . . . ? N2 C30 N3 C34 61.1(5) . . . . ? N2 C30 N3 C31 -58.1(6) . . . . ? N1 C33 N4 C32 58.4(5) . . . . ? N1 C33 N4 C31 -60.1(6) . . . . ? N2 C32 N4 C33 -60.9(5) . . . . ? N2 C32 N4 C31 57.1(6) . . . . ? N3 C31 N4 C33 60.8(6) . . . . ? N3 C31 N4 C32 -57.3(6) . . . . ? N6 C35 N5 C39 58.8(6) . . . . ? N6 C35 N5 C40 -60.6(6) . . . . ? N8 C39 N5 C35 -59.2(5) . . . . ? N8 C39 N5 C40 60.1(5) . . . . ? N7 C40 N5 C35 60.5(5) . . . . ? N7 C40 N5 C39 -59.6(5) . . . . ? N5 C35 N6 C36 59.5(6) . . . . ? N5 C35 N6 C38 -58.7(6) . . . . ? N7 C36 N6 C35 -60.5(7) . . . . ? N7 C36 N6 C38 57.5(7) . . . . ? N8 C38 N6 C35 61.3(6) . . . . ? N8 C38 N6 C36 -56.7(6) . . . . ? N5 C40 N7 C36 -59.3(5) . . . . ? N5 C40 N7 C37 58.5(5) . . . . ? N6 C36 N7 C40 60.6(6) . . . . ? N6 C36 N7 C37 -57.5(6) . . . . ? N8 C37 N7 C40 -59.9(5) . . . . ? N8 C37 N7 C36 57.7(6) . . . . ? N5 C39 N8 C37 -59.7(5) . . . . ? N5 C39 N8 C38 59.2(5) . . . . ? N7 C37 N8 C39 60.2(6) . . . . ? N7 C37 N8 C38 -57.9(6) . . . . ? N6 C38 N8 C39 -61.4(6) . . . . ? N6 C38 N8 C37 57.3(6) . . . . ? 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 O3 H3 O2 0.92(6) 1.69(6) 2.601(5) 169(5) 2_546 O5 H5 O9 0.96(7) 1.63(7) 2.572(5) 166(7) 3_566 O7 H7 O1 0.98(6) 1.68(6) 2.649(5) 169(5) 2_556 O11 H11 N4 1.07(8) 1.72(8) 2.767(6) 164(6) 4_575 O13 H13 O10 0.97(6) 1.71(6) 2.679(5) 175(5) 3_666 O15 H15 N7 0.96(7) 1.78(7) 2.719(6) 164(6) 1_565 N1 H1 O1 1.00(7) 1.99(7) 2.834(6) 140(5) . N1 H1 O2 1.00(7) 1.96(7) 2.887(6) 152(5) . N5 H5A O9 0.80(6) 2.46(6) 2.976(5) 123(5) . N5 H5A O10 0.80(6) 1.94(6) 2.734(5) 172(6) . ###END