# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- All CIF.cif' _publ_contact_author_name 'Dr. Gopal Das' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_contact_author_email gdas@iitg.ernet.in _publ_contact_author_phone 00913612582313 _publ_contact_author_fax 00913612582349 loop_ _publ_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_author_name G.Das data_amide _database_code_depnum_ccdc_archive 'CCDC 795525' #TrackingRef '- All CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 N10 O15, C2 H6 O S' _chemical_formula_sum 'C29 H30 N10 O16 S' _chemical_formula_weight 806.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2942(3) _cell_length_b 12.4744(4) _cell_length_c 12.8671(4) _cell_angle_alpha 84.723(2) _cell_angle_beta 79.650(3) _cell_angle_gamma 88.404(2) _cell_volume 1775.65(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3478 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 19.56 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13679 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.29 _reflns_number_total 8734 _reflns_number_gt 7605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0817P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7399 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 N1 N 0.26303(14) 0.30768(14) 0.19610(13) 0.0449(4) Uani 1 1 d . . . C1 C 0.24656(18) 0.29037(18) 0.08872(16) 0.0500(5) Uani 1 1 d . . . H1A H 0.2786 0.3516 0.0410 0.060 Uiso 1 1 calc R . . H1B H 0.1610 0.2874 0.0878 0.060 Uiso 1 1 calc R . . C2 C 0.3061(2) 0.18919(19) 0.04752(18) 0.0556(6) Uani 1 1 d . . . H2A H 0.2759 0.1275 0.0955 0.067 Uiso 1 1 calc R . . H2B H 0.2858 0.1802 -0.0212 0.067 Uiso 1 1 calc R . . N2 N 0.43601(17) 0.19312(18) 0.03769(16) 0.0533(5) Uani 1 1 d . . . C3 C 0.4990(2) 0.1213(2) 0.08783(17) 0.0513(5) Uani 1 1 d . . . C8 C 0.8248(2) 0.0778(2) 0.10507(16) 0.0531(6) Uani 1 1 d . . . C9 C 0.7065(2) 0.05879(19) 0.10065(15) 0.0524(6) Uani 1 1 d . . . H9 H 0.6778 -0.0112 0.1091 0.063 Uiso 1 1 calc R . . C5 C 0.6756(2) 0.24945(19) 0.07235(16) 0.0505(5) Uani 1 1 d . . . H5 H 0.6264 0.3085 0.0596 0.061 Uiso 1 1 calc R . . C4 C 0.63048(19) 0.14568(18) 0.08342(15) 0.0482(5) Uani 1 1 d . . . C7 C 0.8713(2) 0.1789(2) 0.09642(17) 0.0568(6) Uani 1 1 d . . . H7 H 0.9513 0.1898 0.1010 0.068 Uiso 1 1 calc R . . C6 C 0.7943(2) 0.26392(19) 0.08058(16) 0.0528(6) Uani 1 1 d . . . C10 C 0.17952(18) 0.2406(2) 0.27431(16) 0.0540(6) Uani 1 1 d . . . H10A H 0.1729 0.1713 0.2475 0.065 Uiso 1 1 calc R . . H10B H 0.1005 0.2746 0.2831 0.065 Uiso 1 1 calc R . . C11 C 0.21828(19) 0.2230(2) 0.38153(17) 0.0559(6) Uani 1 1 d . . . H11A H 0.2315 0.2923 0.4059 0.067 Uiso 1 1 calc R . . H11B H 0.1542 0.1876 0.4323 0.067 Uiso 1 1 calc R . . N5 N 0.32764(16) 0.15806(18) 0.37768(14) 0.0498(5) Uani 1 1 d . . . C12 C 0.43551(19) 0.20106(19) 0.37011(16) 0.0479(5) Uani 1 1 d . . . C18 C 0.64847(18) 0.16853(18) 0.38085(15) 0.0492(5) Uani 1 1 d . . . H18 H 0.6533 0.2421 0.3860 0.059 Uiso 1 1 calc R . . C13 C 0.54116(18) 0.12410(17) 0.37041(14) 0.0442(5) Uani 1 1 d . . . C16 C 0.74638(19) -0.0054(2) 0.37703(16) 0.0526(6) Uani 1 1 d . . . H16 H 0.8144 -0.0486 0.3800 0.063 Uiso 1 1 calc R . . C17 C 0.74873(18) 0.10290(19) 0.38365(16) 0.0507(6) Uani 1 1 d . . . C14 C 0.53635(19) 0.01391(18) 0.36248(15) 0.0488(5) Uani 1 1 d . . . H14 H 0.4650 -0.0175 0.3551 0.059 Uiso 1 1 calc R . . C15 C 0.6388(2) -0.04803(18) 0.36576(15) 0.0498(5) Uani 1 1 d . . . N3 N 0.84027(18) 0.37407(18) 0.07386(15) 0.0610(5) Uani 1 1 d . . . N4 N 0.9058(2) -0.0146(2) 0.12387(16) 0.0697(6) Uani 1 1 d . . . O3 O 0.92737(16) 0.38725(16) 0.11513(16) 0.0817(6) Uani 1 1 d . . . O2 O 0.78780(17) 0.44527(15) 0.02946(15) 0.0768(5) Uani 1 1 d . . . O1 O 0.45691(15) 0.03856(16) 0.13853(14) 0.0722(5) Uani 1 1 d . . . O4 O 1.01213(19) 0.00211(18) 0.11845(17) 0.0931(7) Uani 1 1 d . . . O5 O 0.8601(2) -0.10330(19) 0.14593(18) 0.0953(7) Uani 1 1 d . . . O6 O 0.45203(14) 0.29843(13) 0.36907(13) 0.0631(4) Uani 1 1 d . . . O10 O 0.86462(15) 0.24762(17) 0.40239(18) 0.0902(6) Uani 1 1 d . . . O9 O 0.95052(16) 0.09295(17) 0.39433(18) 0.0937(7) Uani 1 1 d . . . O8 O 0.72222(19) -0.21917(16) 0.37024(16) 0.0864(6) Uani 1 1 d . . . O7 O 0.5435(2) -0.20069(18) 0.3392(3) 0.1408(11) Uani 1 1 d . . . N7 N 0.86247(18) 0.1521(2) 0.39393(17) 0.0678(6) Uani 1 1 d . . . N6 N 0.6345(2) -0.16436(18) 0.35739(16) 0.0675(6) Uani 1 1 d . . . C20 C 0.3444(2) 0.49462(19) 0.16231(19) 0.0576(6) Uani 1 1 d . . . H20A H 0.3704 0.4779 0.0895 0.069 Uiso 1 1 calc R . . H20B H 0.3157 0.5687 0.1610 0.069 Uiso 1 1 calc R . . C19 C 0.24177(19) 0.42119(19) 0.21429(18) 0.0547(6) Uani 1 1 d . . . H19A H 0.2272 0.4276 0.2901 0.066 Uiso 1 1 calc R . . H19B H 0.1695 0.4455 0.1878 0.066 Uiso 1 1 calc R . . N8 N 0.44721(17) 0.48411(17) 0.21731(15) 0.0535(5) Uani 1 1 d . . . C22 C 0.63805(19) 0.54581(17) 0.25234(16) 0.0483(5) Uani 1 1 d . . . C24 C 0.84470(19) 0.58552(18) 0.24878(18) 0.0532(6) Uani 1 1 d . . . C27 C 0.6323(2) 0.49441(18) 0.35352(17) 0.0520(5) Uani 1 1 d . . . H27 H 0.5617 0.4620 0.3894 0.062 Uiso 1 1 calc R . . C23 C 0.7450(2) 0.59285(17) 0.20167(17) 0.0515(5) Uani 1 1 d . . . H23 H 0.7492 0.6298 0.1350 0.062 Uiso 1 1 calc R . . C21 C 0.5337(2) 0.55530(19) 0.19298(17) 0.0504(5) Uani 1 1 d . . . C25 C 0.8419(2) 0.53589(19) 0.34978(19) 0.0586(6) Uani 1 1 d . . . H25 H 0.9095 0.5321 0.3820 0.070 Uiso 1 1 calc R . . C26 C 0.7341(2) 0.49251(19) 0.39989(17) 0.0562(6) Uani 1 1 d . . . O11 O 0.53381(14) 0.62901(15) 0.12243(13) 0.0679(5) Uani 1 1 d . . . O13 O 1.04587(17) 0.62388(18) 0.23309(18) 0.0947(6) Uani 1 1 d . . . O15 O 0.8139(2) 0.44513(19) 0.55132(15) 0.1017(7) Uani 1 1 d . . . O12 O 0.95904(17) 0.67485(18) 0.10130(19) 0.0890(6) Uani 1 1 d . . . O14 O 0.6343(2) 0.3931(2) 0.54977(15) 0.0965(7) Uani 1 1 d . . . N10 N 0.7267(2) 0.4398(2) 0.50888(16) 0.0712(6) Uani 1 1 d . . . N9 N 0.95809(19) 0.63197(18) 0.1901(2) 0.0677(6) Uani 1 1 d . . . H5N H 0.3273(19) 0.092(2) 0.3768(17) 0.051(7) Uiso 1 1 d . . . H2N H 0.4682(18) 0.2462(18) -0.0017(16) 0.044(7) Uiso 1 1 d . . . H8N H 0.456(2) 0.427(2) 0.267(2) 0.073(8) Uiso 1 1 d . . . S1 S 0.20246(6) 0.91724(6) 0.28883(5) 0.0707(2) Uani 1 1 d . . . O16 O 0.25969(14) 0.94038(14) 0.38030(12) 0.0664(5) Uani 1 1 d . . . C29 C 0.2914(3) 0.8134(3) 0.2268(2) 0.0927(9) Uani 1 1 d . . . H29A H 0.3699 0.8405 0.1964 0.139 Uiso 1 1 calc R . . H29B H 0.2537 0.7896 0.1719 0.139 Uiso 1 1 calc R . . H29C H 0.2986 0.7541 0.2784 0.139 Uiso 1 1 calc R . . C28 C 0.0732(2) 0.8415(2) 0.3450(2) 0.0842(9) Uani 1 1 d . . . H28A H 0.0971 0.7736 0.3769 0.126 Uiso 1 1 calc R . . H28B H 0.0283 0.8293 0.2906 0.126 Uiso 1 1 calc R . . H28C H 0.0239 0.8804 0.3981 0.126 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 N1 0.0379(9) 0.0450(11) 0.0526(9) -0.0020(8) -0.0116(8) -0.0004(8) C1 0.0409(12) 0.0538(14) 0.0589(12) -0.0042(11) -0.0199(10) 0.0034(10) C2 0.0521(14) 0.0537(15) 0.0646(13) -0.0088(11) -0.0176(11) -0.0021(11) N2 0.0487(12) 0.0464(13) 0.0610(12) 0.0063(11) -0.0059(10) 0.0044(10) C3 0.0597(14) 0.0473(14) 0.0450(11) -0.0017(11) -0.0059(11) 0.0010(12) C8 0.0588(14) 0.0554(16) 0.0446(11) -0.0050(11) -0.0106(10) 0.0179(12) C9 0.0626(15) 0.0491(14) 0.0446(11) -0.0042(10) -0.0086(10) 0.0076(12) C5 0.0525(14) 0.0499(14) 0.0476(11) -0.0029(11) -0.0074(10) 0.0099(11) C4 0.0525(13) 0.0506(14) 0.0402(10) -0.0040(10) -0.0061(9) 0.0087(11) C7 0.0511(14) 0.0684(17) 0.0524(12) -0.0090(12) -0.0135(10) 0.0121(13) C6 0.0541(14) 0.0554(15) 0.0481(11) -0.0066(11) -0.0064(10) 0.0025(12) C10 0.0381(12) 0.0623(16) 0.0620(13) 0.0005(12) -0.0132(10) -0.0010(11) C11 0.0417(12) 0.0663(16) 0.0574(13) 0.0021(12) -0.0071(10) 0.0014(11) N5 0.0441(11) 0.0491(13) 0.0579(11) -0.0001(10) -0.0156(8) 0.0011(10) C12 0.0481(13) 0.0493(14) 0.0486(11) 0.0003(10) -0.0172(10) -0.0007(11) C18 0.0497(13) 0.0499(14) 0.0482(11) -0.0023(10) -0.0099(10) -0.0049(11) C13 0.0441(12) 0.0489(13) 0.0400(10) 0.0005(10) -0.0110(9) -0.0017(10) C16 0.0468(13) 0.0634(16) 0.0470(11) -0.0065(11) -0.0071(9) 0.0094(11) C17 0.0400(12) 0.0609(16) 0.0523(12) -0.0071(11) -0.0101(9) -0.0004(11) C14 0.0479(13) 0.0529(14) 0.0468(11) 0.0002(10) -0.0137(9) -0.0033(11) C15 0.0553(14) 0.0504(14) 0.0438(11) -0.0027(10) -0.0097(10) 0.0014(11) N3 0.0592(13) 0.0642(15) 0.0619(12) -0.0127(11) -0.0133(10) 0.0022(11) N4 0.0785(17) 0.0661(17) 0.0692(13) -0.0139(12) -0.0263(12) 0.0264(14) O3 0.0654(11) 0.0808(13) 0.1085(14) -0.0239(11) -0.0336(10) 0.0022(10) O2 0.0858(13) 0.0576(12) 0.0928(13) 0.0004(10) -0.0358(11) 0.0032(10) O1 0.0706(11) 0.0622(12) 0.0815(11) 0.0196(10) -0.0189(9) -0.0085(9) O4 0.0727(14) 0.1012(17) 0.1120(15) -0.0078(12) -0.0394(12) 0.0311(12) O5 0.1052(16) 0.0635(14) 0.1233(17) -0.0098(13) -0.0401(13) 0.0268(13) O6 0.0579(10) 0.0508(11) 0.0853(11) 0.0014(9) -0.0287(8) -0.0014(8) O10 0.0566(11) 0.0760(15) 0.1413(18) -0.0207(13) -0.0197(11) -0.0097(10) O9 0.0398(10) 0.0910(15) 0.1518(19) -0.0219(13) -0.0164(11) 0.0059(10) O8 0.0939(15) 0.0653(13) 0.1050(14) -0.0200(11) -0.0282(11) 0.0236(11) O7 0.1064(18) 0.0620(14) 0.279(4) -0.0374(18) -0.090(2) 0.0028(13) N7 0.0470(13) 0.0732(17) 0.0831(14) -0.0118(12) -0.0082(10) -0.0020(12) N6 0.0749(16) 0.0539(14) 0.0767(13) -0.0111(11) -0.0203(11) 0.0083(12) C20 0.0608(14) 0.0489(14) 0.0695(14) -0.0025(11) -0.0298(12) -0.0013(11) C19 0.0480(13) 0.0565(15) 0.0621(13) -0.0092(11) -0.0154(11) 0.0074(11) N8 0.0584(12) 0.0484(12) 0.0573(11) 0.0044(10) -0.0237(9) -0.0044(10) C22 0.0510(13) 0.0453(13) 0.0507(12) -0.0066(10) -0.0142(10) 0.0047(10) C24 0.0483(13) 0.0477(13) 0.0662(14) -0.0165(11) -0.0120(11) 0.0030(10) C27 0.0536(13) 0.0512(14) 0.0529(12) -0.0075(11) -0.0123(10) 0.0009(11) C23 0.0578(14) 0.0448(13) 0.0532(12) -0.0066(10) -0.0126(11) 0.0017(11) C21 0.0542(14) 0.0479(14) 0.0506(12) -0.0023(11) -0.0146(10) 0.0002(11) C25 0.0549(14) 0.0568(15) 0.0714(15) -0.0217(12) -0.0244(12) 0.0091(12) C26 0.0691(16) 0.0523(14) 0.0521(12) -0.0119(11) -0.0217(11) 0.0091(12) O11 0.0645(11) 0.0680(12) 0.0711(10) 0.0212(10) -0.0245(8) -0.0090(9) O13 0.0554(11) 0.1035(17) 0.1317(17) -0.0264(13) -0.0252(12) -0.0034(11) O15 0.1149(16) 0.1296(19) 0.0749(12) -0.0116(12) -0.0553(12) 0.0070(14) O12 0.0704(13) 0.0887(16) 0.0988(15) 0.0072(12) 0.0032(11) -0.0121(11) O14 0.1038(16) 0.120(2) 0.0629(12) 0.0186(12) -0.0203(11) -0.0100(15) N10 0.0895(17) 0.0758(16) 0.0546(12) -0.0092(11) -0.0297(13) 0.0104(14) N9 0.0508(13) 0.0558(14) 0.0984(17) -0.0250(13) -0.0096(13) 0.0014(10) S1 0.0811(5) 0.0608(4) 0.0774(4) 0.0010(3) -0.0351(4) -0.0110(4) O16 0.0650(10) 0.0687(11) 0.0692(10) -0.0077(8) -0.0194(8) -0.0142(9) C29 0.096(2) 0.100(2) 0.0826(19) -0.0285(17) -0.0040(16) -0.0158(19) C28 0.0640(17) 0.083(2) 0.113(2) -0.0172(17) -0.0292(16) -0.0100(15) _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 N1 C1 1.463(2) . ? N1 C19 1.463(3) . ? N1 C10 1.466(3) . ? C1 C2 1.508(3) . ? C2 N2 1.452(3) . ? N2 C3 1.322(3) . ? C3 O1 1.228(3) . ? C3 C4 1.514(3) . ? C8 C7 1.368(3) . ? C8 C9 1.375(3) . ? C8 N4 1.481(3) . ? C9 C4 1.391(3) . ? C5 C6 1.382(3) . ? C5 C4 1.390(3) . ? C7 C6 1.376(3) . ? C6 N3 1.472(3) . ? C10 C11 1.516(3) . ? C11 N5 1.454(3) . ? N5 C12 1.329(3) . ? C12 O6 1.233(3) . ? C12 C13 1.511(3) . ? C18 C13 1.380(3) . ? C18 C17 1.383(3) . ? C13 C14 1.391(3) . ? C16 C17 1.363(3) . ? C16 C15 1.376(3) . ? C17 N7 1.471(3) . ? C14 C15 1.378(3) . ? C15 N6 1.468(3) . ? N3 O2 1.211(2) . ? N3 O3 1.220(2) . ? N4 O4 1.213(3) . ? N4 O5 1.222(3) . ? O10 N7 1.208(3) . ? O9 N7 1.222(3) . ? O8 N6 1.215(2) . ? O7 N6 1.204(3) . ? C20 N8 1.462(3) . ? C20 C19 1.516(3) . ? N8 C21 1.314(3) . ? C22 C23 1.384(3) . ? C22 C27 1.389(3) . ? C22 C21 1.512(3) . ? C24 C23 1.368(3) . ? C24 C25 1.383(3) . ? C24 N9 1.469(3) . ? C27 C26 1.385(3) . ? C21 O11 1.231(3) . ? C25 C26 1.372(3) . ? C26 N10 1.482(3) . ? O13 N9 1.217(3) . ? O15 N10 1.215(3) . ? O12 N9 1.215(3) . ? O14 N10 1.219(3) . ? S1 O16 1.4942(16) . ? S1 C28 1.766(3) . ? S1 C29 1.775(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C19 109.75(16) . . ? C1 N1 C10 110.11(16) . . ? C19 N1 C10 109.73(17) . . ? N1 C1 C2 114.19(17) . . ? N2 C2 C1 111.40(18) . . ? C3 N2 C2 123.2(2) . . ? O1 C3 N2 124.2(2) . . ? O1 C3 C4 119.0(2) . . ? N2 C3 C4 116.8(2) . . ? C7 C8 C9 123.1(2) . . ? C7 C8 N4 117.7(2) . . ? C9 C8 N4 119.2(2) . . ? C8 C9 C4 119.1(2) . . ? C6 C5 C4 119.2(2) . . ? C5 C4 C9 119.2(2) . . ? C5 C4 C3 123.52(19) . . ? C9 C4 C3 117.1(2) . . ? C8 C7 C6 116.9(2) . . ? C7 C6 C5 122.4(2) . . ? C7 C6 N3 118.4(2) . . ? C5 C6 N3 119.1(2) . . ? N1 C10 C11 113.15(17) . . ? N5 C11 C10 112.21(18) . . ? C12 N5 C11 122.5(2) . . ? O6 C12 N5 123.6(2) . . ? O6 C12 C13 119.23(19) . . ? N5 C12 C13 117.0(2) . . ? C13 C18 C17 119.5(2) . . ? C18 C13 C14 119.13(19) . . ? C18 C13 C12 116.15(19) . . ? C14 C13 C12 124.72(18) . . ? C17 C16 C15 117.0(2) . . ? C16 C17 C18 122.6(2) . . ? C16 C17 N7 118.8(2) . . ? C18 C17 N7 118.6(2) . . ? C15 C14 C13 119.10(19) . . ? C16 C15 C14 122.7(2) . . ? C16 C15 N6 117.9(2) . . ? C14 C15 N6 119.4(2) . . ? O2 N3 O3 124.7(2) . . ? O2 N3 C6 117.71(19) . . ? O3 N3 C6 117.5(2) . . ? O4 N4 O5 124.1(2) . . ? O4 N4 C8 118.6(3) . . ? O5 N4 C8 117.3(2) . . ? O10 N7 O9 123.2(2) . . ? O10 N7 C17 119.2(2) . . ? O9 N7 C17 117.6(2) . . ? O7 N6 O8 123.4(2) . . ? O7 N6 C15 118.1(2) . . ? O8 N6 C15 118.5(2) . . ? N8 C20 C19 112.65(19) . . ? N1 C19 C20 114.29(18) . . ? C21 N8 C20 119.3(2) . . ? C23 C22 C27 118.84(19) . . ? C23 C22 C21 116.95(19) . . ? C27 C22 C21 124.2(2) . . ? C23 C24 C25 122.0(2) . . ? C23 C24 N9 118.9(2) . . ? C25 C24 N9 119.1(2) . . ? C26 C27 C22 118.6(2) . . ? C24 C23 C22 120.6(2) . . ? O11 C21 N8 122.4(2) . . ? O11 C21 C22 118.5(2) . . ? N8 C21 C22 119.1(2) . . ? C26 C25 C24 116.4(2) . . ? C25 C26 C27 123.4(2) . . ? C25 C26 N10 118.2(2) . . ? C27 C26 N10 118.4(2) . . ? O15 N10 O14 124.2(2) . . ? O15 N10 C26 117.7(3) . . ? O14 N10 C26 118.1(2) . . ? O12 N9 O13 123.9(2) . . ? O12 N9 C24 118.2(2) . . ? O13 N9 C24 117.9(2) . . ? O16 S1 C28 105.42(12) . . ? O16 S1 C29 105.79(12) . . ? C28 S1 C29 98.63(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.620 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.041 data_Amide(F)-H2O _database_code_depnum_ccdc_archive 'CCDC 795526' #TrackingRef '- All CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 N10 O15, C16 H36 N, F, O' _chemical_formula_sum 'C43 H60 F N11 O16' _chemical_formula_weight 1006.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 16.129(3) _cell_length_b 15.781(2) _cell_length_c 25.393(4) _cell_angle_alpha 90.00 _cell_angle_beta 127.592(9) _cell_angle_gamma 90.00 _cell_volume 5121.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3872 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 20.59 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35440 _diffrn_reflns_av_R_equivalents 0.0935 _diffrn_reflns_av_sigmaI/netI 0.0837 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 24.89 _reflns_number_total 8854 _reflns_number_gt 7719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0200P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8791 _refine_ls_number_parameters 644 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.2034 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 O1 O 0.73045(19) 0.06669(16) 0.11641(14) 0.0968(8) Uani 1 1 d . . . O2 O 0.4724(3) -0.14156(19) 0.03603(18) 0.1235(11) Uani 1 1 d . . . O3 O 0.3459(3) -0.1302(2) 0.04013(19) 0.1423(13) Uani 1 1 d . . . O4 O 0.4337(3) 0.2165(2) 0.1776(2) 0.1280(11) Uani 1 1 d . . . O5 O 0.3305(3) 0.1137(2) 0.1492(2) 0.1442(14) Uani 1 1 d . . . O6 O 0.85852(19) 0.54667(16) 0.30281(12) 0.0920(7) Uani 1 1 d . . . O7 O 0.7108(3) 0.1796(2) 0.31284(18) 0.1327(12) Uani 1 1 d . . . O8 O 0.7274(3) 0.1873(2) 0.40310(19) 0.1359(12) Uani 1 1 d . . . O9 O 0.9096(3) 0.5452(3) 0.50824(17) 0.1387(14) Uani 1 1 d . . . O10 O 0.8930(3) 0.4287(3) 0.5459(2) 0.1653(17) Uani 1 1 d . . . O11 O 0.33807(17) 0.38587(15) -0.04375(11) 0.0779(6) Uani 1 1 d . . . O12 O 0.1034(2) 0.5544(2) -0.03119(16) 0.1179(10) Uani 1 1 d . . . O13 O 0.1064(2) 0.5456(2) 0.05439(15) 0.1236(11) Uani 1 1 d . . . O14 O 0.5432(2) 0.3931(2) 0.26143(13) 0.1267(12) Uani 1 1 d . . . O15 O 0.4181(2) 0.4418(2) 0.25918(12) 0.1022(9) Uani 1 1 d . . . N1 N 0.7280(2) 0.36122(16) 0.10568(13) 0.0689(7) Uani 1 1 d . . . N2 N 0.72557(19) 0.19383(17) 0.15542(14) 0.0762(8) Uani 1 1 d . . . H2 H 0.6947 0.2242 0.1669 0.091 Uiso 1 1 d R . . N3 N 0.4242(3) -0.1033(2) 0.05023(16) 0.0890(9) Uani 1 1 d . . . N4 N 0.4032(3) 0.1467(2) 0.15493(17) 0.0901(9) Uani 1 1 d . . . N5 N 0.7627(2) 0.44606(17) 0.22432(14) 0.0744(7) Uani 1 1 d . . . H5A H 0.7292 0.3991 0.2143 0.089 Uiso 1 1 d R . . N6 N 0.7337(3) 0.2177(2) 0.3617(2) 0.0951(10) Uani 1 1 d . . . N7 N 0.8844(3) 0.4712(4) 0.5024(2) 0.1106(13) Uani 1 1 d . . . N8 N 0.50061(19) 0.35751(16) 0.04890(12) 0.0656(7) Uani 1 1 d . . . H8A H 0.5409 0.3533 0.0915 0.079 Uiso 1 1 d R . . N9 N 0.1419(2) 0.5309(2) 0.02482(18) 0.0876(9) Uani 1 1 d . . . N10 N 0.4552(2) 0.4202(2) 0.23163(13) 0.0768(8) Uani 1 1 d . . . C1 C 0.7799(3) 0.2861(2) 0.1048(2) 0.0841(10) Uani 1 1 d . . . H1A H 0.8397 0.3031 0.1070 0.101 Uiso 1 1 calc R . . H1B H 0.7319 0.2555 0.0635 0.101 Uiso 1 1 calc R . . C2 C 0.8159(3) 0.2285(2) 0.1629(2) 0.0899(11) Uani 1 1 d . . . H2A H 0.8577 0.1827 0.1648 0.108 Uiso 1 1 calc R . . H2B H 0.8590 0.2602 0.2041 0.108 Uiso 1 1 calc R . . C3 C 0.6898(2) 0.1172(2) 0.13148(17) 0.0705(9) Uani 1 1 d . . . C4 C 0.5911(2) 0.08877(19) 0.12200(15) 0.0604(8) Uani 1 1 d . . . C5 C 0.5503(2) 0.01149(19) 0.09086(15) 0.0642(8) Uani 1 1 d . . . H5 H 0.5819 -0.0191 0.0761 0.077 Uiso 1 1 calc R . . C6 C 0.4634(3) -0.01986(19) 0.08182(15) 0.0665(8) Uani 1 1 d . . . C7 C 0.4139(2) 0.0223(2) 0.10251(16) 0.0708(9) Uani 1 1 d . . . H7 H 0.3550 0.0002 0.0963 0.085 Uiso 1 1 calc R . . C8 C 0.4555(2) 0.0992(2) 0.13301(15) 0.0639(8) Uani 1 1 d . . . C9 C 0.5431(2) 0.13398(19) 0.14368(15) 0.0633(8) Uani 1 1 d . . . H9 H 0.5692 0.1861 0.1647 0.076 Uiso 1 1 calc R . . C10 C 0.8023(3) 0.4296(2) 0.14602(19) 0.0811(10) Uani 1 1 d . . . H10A H 0.8140 0.4623 0.1187 0.097 Uiso 1 1 calc R . . H10B H 0.8687 0.4049 0.1821 0.097 Uiso 1 1 calc R . . C11 C 0.7653(3) 0.4884(2) 0.17474(18) 0.0825(10) Uani 1 1 d . . . H11A H 0.8118 0.5368 0.1948 0.099 Uiso 1 1 calc R . . H11B H 0.6959 0.5090 0.1393 0.099 Uiso 1 1 calc R . . C12 C 0.8112(2) 0.4783(2) 0.28528(17) 0.0716(9) Uani 1 1 d . . . C13 C 0.8067(2) 0.4282(2) 0.33381(15) 0.0647(8) Uani 1 1 d . . . C18 C 0.7712(2) 0.3454(2) 0.32401(16) 0.0689(8) Uani 1 1 d . . . H18 H 0.7463 0.3171 0.2848 0.083 Uiso 1 1 calc R . . C17 C 0.7730(2) 0.3054(2) 0.37291(17) 0.0732(9) Uani 1 1 d . . . C16 C 0.8094(3) 0.3447(3) 0.43201(18) 0.0820(10) Uani 1 1 d . . . H16 H 0.8101 0.3172 0.4647 0.098 Uiso 1 1 calc R . . C15 C 0.8447(2) 0.4267(3) 0.44003(18) 0.0805(10) Uani 1 1 d . . . C14 C 0.8437(2) 0.4686(2) 0.39289(18) 0.0755(9) Uani 1 1 d . . . H14 H 0.8678 0.5241 0.4003 0.091 Uiso 1 1 calc R . . C19 C 0.6398(3) 0.3884(2) 0.03921(17) 0.0757(9) Uani 1 1 d . . . H19A H 0.6577 0.3817 0.0093 0.091 Uiso 1 1 calc R . . H19B H 0.6263 0.4480 0.0403 0.091 Uiso 1 1 calc R . . C20 C 0.5419(2) 0.3381(2) 0.01301(17) 0.0753(9) Uani 1 1 d . . . H20A H 0.4892 0.3508 -0.0337 0.090 Uiso 1 1 calc R . . H20B H 0.5576 0.2781 0.0170 0.090 Uiso 1 1 calc R . . C21 C 0.4021(2) 0.38153(18) 0.01726(15) 0.0592(8) Uani 1 1 d . . . C22 C 0.3685(2) 0.40827(18) 0.05858(14) 0.0546(7) Uani 1 1 d . . . C27 C 0.4281(2) 0.39749(18) 0.12681(14) 0.0582(7) Uani 1 1 d . . . H27 H 0.4918 0.3691 0.1501 0.070 Uiso 1 1 calc R . . C26 C 0.3911(2) 0.42969(19) 0.15948(14) 0.0597(8) Uani 1 1 d . . . C25 C 0.2980(2) 0.4730(2) 0.12754(16) 0.0647(8) Uani 1 1 d . . . H25 H 0.2753 0.4950 0.1507 0.078 Uiso 1 1 calc R . . C24 C 0.2405(2) 0.4822(2) 0.06022(15) 0.0628(8) Uani 1 1 d . . . C23 C 0.2733(2) 0.45051(19) 0.02551(15) 0.0619(8) Uani 1 1 d . . . H23 H 0.2318 0.4572 -0.0204 0.074 Uiso 1 1 calc R . . N11 N 0.19050(17) 0.32075(15) 0.24747(12) 0.0635(7) Uani 1 1 d . . . C40 C 0.1171(2) 0.2765(2) 0.18038(16) 0.0715(9) Uani 1 1 d . . . H40A H 0.1228 0.2158 0.1880 0.086 Uiso 1 1 calc R . . H40B H 0.0458 0.2926 0.1612 0.086 Uiso 1 1 calc R . . C41 C 0.1363(3) 0.2949(2) 0.13060(17) 0.0833(10) Uani 1 1 d . . . H41A H 0.2068 0.2777 0.1487 0.100 Uiso 1 1 calc R . . H41B H 0.1305 0.3554 0.1223 0.100 Uiso 1 1 calc R . . C42 C 0.0593(3) 0.2490(3) 0.06589(19) 0.1012(12) Uani 1 1 d . . . H42A H 0.0663 0.1885 0.0744 0.121 Uiso 1 1 calc R . . H42B H -0.0111 0.2651 0.0488 0.121 Uiso 1 1 calc R . . C43 C 0.0736(4) 0.2669(3) 0.0140(2) 0.1240(16) Uani 1 1 d . . . H43A H 0.0536 0.3244 -0.0010 0.186 Uiso 1 1 calc R . . H43B H 0.0306 0.2291 -0.0228 0.186 Uiso 1 1 calc R . . H43C H 0.1457 0.2588 0.0326 0.186 Uiso 1 1 calc R . . C28 C 0.1892(2) 0.41611(19) 0.23912(16) 0.0654(8) Uani 1 1 d . . . H28A H 0.2352 0.4411 0.2831 0.078 Uiso 1 1 calc R . . H28B H 0.2192 0.4281 0.2164 0.078 Uiso 1 1 calc R . . C29 C 0.0852(2) 0.4609(2) 0.20207(17) 0.0712(9) Uani 1 1 d . . . H29A H 0.0568 0.4553 0.2263 0.085 Uiso 1 1 calc R . . H29B H 0.0363 0.4353 0.1586 0.085 Uiso 1 1 calc R . . C30 C 0.0994(3) 0.5540(2) 0.19430(19) 0.0870(11) Uani 1 1 d . . . H30A H 0.1524 0.5774 0.2380 0.104 Uiso 1 1 calc R . . H30B H 0.1254 0.5584 0.1686 0.104 Uiso 1 1 calc R . . C31 C 0.0031(3) 0.6065(3) 0.1616(2) 0.1191(16) Uani 1 1 d . . . H31A H -0.0500 0.5843 0.1181 0.179 Uiso 1 1 calc R . . H31B H 0.0187 0.6639 0.1577 0.179 Uiso 1 1 calc R . . H31C H -0.0214 0.6053 0.1878 0.179 Uiso 1 1 calc R . . C32 C 0.1557(2) 0.2974(2) 0.28890(16) 0.0712(9) Uani 1 1 d . . . H32A H 0.1512 0.2362 0.2894 0.085 Uiso 1 1 calc R . . H32B H 0.0859 0.3198 0.2673 0.085 Uiso 1 1 calc R . . C33 C 0.2249(3) 0.3285(2) 0.35972(17) 0.0818(10) Uani 1 1 d . . . H33A H 0.2298 0.3898 0.3598 0.098 Uiso 1 1 calc R . . H33B H 0.2947 0.3056 0.3820 0.098 Uiso 1 1 calc R . . C34 C 0.1848(3) 0.3034(3) 0.3979(2) 0.0999(12) Uani 1 1 d . . . H34A H 0.1154 0.3269 0.3762 0.120 Uiso 1 1 calc R . . H34B H 0.1793 0.2422 0.3978 0.120 Uiso 1 1 calc R . . C35 C 0.2564(4) 0.3346(4) 0.4686(2) 0.1351(18) Uani 1 1 d . . . H35A H 0.3243 0.3095 0.4907 0.203 Uiso 1 1 calc R . . H35B H 0.2282 0.3192 0.4914 0.203 Uiso 1 1 calc R . . H35C H 0.2624 0.3952 0.4688 0.203 Uiso 1 1 calc R . . C36 C 0.3032(2) 0.2930(2) 0.28134(16) 0.0702(9) Uani 1 1 d . . . H36A H 0.3217 0.3089 0.2528 0.084 Uiso 1 1 calc R . . H36B H 0.3481 0.3251 0.3222 0.084 Uiso 1 1 calc R . . C37 C 0.3284(2) 0.2009(2) 0.29797(18) 0.0788(10) Uani 1 1 d . . . H37A H 0.2842 0.1670 0.2580 0.095 Uiso 1 1 calc R . . H37B H 0.3155 0.1840 0.3291 0.095 Uiso 1 1 calc R . . C38 C 0.4436(3) 0.1867(2) 0.3287(2) 0.0880(11) Uani 1 1 d . . . H38A H 0.4573 0.2107 0.2995 0.106 Uiso 1 1 calc R . . H38B H 0.4868 0.2166 0.3708 0.106 Uiso 1 1 calc R . . C39 C 0.4737(3) 0.0969(3) 0.3401(2) 0.1182(15) Uani 1 1 d . . . H39A H 0.4583 0.0721 0.3677 0.177 Uiso 1 1 calc R . . H39B H 0.5473 0.0922 0.3616 0.177 Uiso 1 1 calc R . . H39C H 0.4352 0.0677 0.2982 0.177 Uiso 1 1 calc R . . F1 F 0.63129(12) 0.31097(10) 0.17887(8) 0.0671(5) Uani 1 1 d . . . O16 O 0.0507(3) 0.5128(3) 0.31535(19) 0.1768(18) 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 O1 0.0858(17) 0.0798(17) 0.143(2) -0.0100(15) 0.0794(18) 0.0041(13) O2 0.123(2) 0.083(2) 0.158(3) -0.0432(19) 0.083(2) -0.0175(17) O3 0.149(3) 0.130(3) 0.182(3) -0.071(2) 0.119(3) -0.079(2) O4 0.166(3) 0.083(2) 0.209(3) -0.030(2) 0.153(3) -0.022(2) O5 0.136(3) 0.139(3) 0.227(4) -0.050(2) 0.147(3) -0.041(2) O6 0.0884(17) 0.0719(16) 0.0953(18) -0.0169(13) 0.0455(15) -0.0192(14) O7 0.187(3) 0.091(2) 0.108(2) -0.0066(18) 0.083(2) -0.027(2) O8 0.179(3) 0.120(3) 0.142(3) 0.026(2) 0.115(3) -0.004(2) O9 0.130(3) 0.138(3) 0.107(2) -0.044(2) 0.051(2) 0.008(2) O10 0.157(3) 0.245(5) 0.086(2) -0.044(3) 0.070(2) -0.038(3) O11 0.0736(14) 0.0954(17) 0.0511(14) 0.0010(11) 0.0309(12) 0.0110(12) O12 0.0893(19) 0.159(3) 0.0775(19) 0.0135(19) 0.0367(16) 0.0468(18) O13 0.0755(17) 0.194(3) 0.103(2) -0.007(2) 0.0559(17) 0.0318(18) O14 0.084(2) 0.215(4) 0.0600(16) 0.0165(18) 0.0336(15) 0.044(2) O15 0.0836(17) 0.167(3) 0.0635(15) -0.0112(15) 0.0487(14) -0.0124(16) N1 0.0660(16) 0.0620(17) 0.0789(18) -0.0005(13) 0.0443(15) -0.0049(13) N2 0.0599(16) 0.0600(18) 0.107(2) 0.0048(15) 0.0503(16) 0.0016(13) N3 0.093(2) 0.077(2) 0.090(2) -0.0154(17) 0.053(2) -0.0183(19) N4 0.097(2) 0.084(2) 0.115(3) -0.0043(19) 0.078(2) -0.0061(19) N5 0.0756(18) 0.0658(17) 0.0695(19) -0.0024(14) 0.0379(16) -0.0115(13) N6 0.102(2) 0.087(3) 0.089(3) 0.017(2) 0.055(2) 0.0048(19) N7 0.077(2) 0.164(4) 0.073(3) -0.025(3) 0.037(2) 0.002(2) N8 0.0562(16) 0.0826(19) 0.0518(14) -0.0082(13) 0.0296(13) 0.0009(13) N9 0.0606(18) 0.115(3) 0.069(2) -0.0061(18) 0.0303(18) 0.0107(16) N10 0.0657(19) 0.107(2) 0.0539(18) -0.0064(15) 0.0344(16) -0.0116(16) C1 0.071(2) 0.073(2) 0.123(3) -0.005(2) 0.067(2) -0.0049(18) C2 0.0573(19) 0.072(2) 0.131(3) 0.013(2) 0.052(2) 0.0023(16) C3 0.0609(19) 0.060(2) 0.089(2) 0.0066(18) 0.0449(19) 0.0055(16) C4 0.0581(17) 0.0505(18) 0.0630(19) 0.0052(14) 0.0320(16) 0.0039(14) C5 0.0630(19) 0.060(2) 0.064(2) 0.0052(15) 0.0360(17) 0.0076(15) C6 0.068(2) 0.0537(19) 0.064(2) -0.0015(15) 0.0334(17) -0.0088(16) C7 0.0611(19) 0.075(2) 0.072(2) 0.0042(18) 0.0382(18) -0.0068(17) C8 0.0630(19) 0.062(2) 0.067(2) 0.0040(16) 0.0396(17) -0.0004(16) C9 0.0636(18) 0.0570(19) 0.0644(19) 0.0001(15) 0.0365(16) -0.0035(15) C10 0.077(2) 0.075(2) 0.093(3) -0.0003(19) 0.053(2) -0.0146(18) C11 0.101(3) 0.065(2) 0.079(2) -0.0008(18) 0.053(2) -0.0144(19) C12 0.0563(19) 0.072(2) 0.070(2) -0.0049(18) 0.0294(17) -0.0022(17) C13 0.0466(16) 0.070(2) 0.057(2) -0.0039(17) 0.0216(15) 0.0015(15) C18 0.0544(18) 0.074(2) 0.0585(19) 0.0023(17) 0.0243(16) 0.0085(16) C17 0.0578(19) 0.080(3) 0.065(2) 0.0094(19) 0.0289(17) 0.0090(16) C16 0.0566(19) 0.116(3) 0.062(2) 0.012(2) 0.0302(18) 0.022(2) C15 0.0484(19) 0.110(3) 0.057(2) -0.015(2) 0.0193(17) 0.0093(19) C14 0.0460(18) 0.089(3) 0.066(2) -0.010(2) 0.0214(17) 0.0043(16) C19 0.080(2) 0.083(2) 0.073(2) 0.0037(18) 0.051(2) 0.0042(18) C20 0.066(2) 0.088(2) 0.070(2) -0.0177(18) 0.0409(18) -0.0046(17) C21 0.0602(19) 0.0583(19) 0.0506(19) -0.0030(14) 0.0295(17) -0.0046(14) C22 0.0534(17) 0.0580(18) 0.0479(17) -0.0016(13) 0.0284(15) -0.0048(13) C27 0.0566(17) 0.0586(19) 0.0553(19) 0.0026(14) 0.0320(16) -0.0018(13) C26 0.0556(18) 0.069(2) 0.0502(18) -0.0055(15) 0.0302(16) -0.0124(15) C25 0.0540(18) 0.078(2) 0.065(2) -0.0083(16) 0.0375(17) -0.0079(15) C24 0.0459(16) 0.072(2) 0.059(2) -0.0034(15) 0.0260(16) 0.0011(14) C23 0.0503(17) 0.072(2) 0.0503(17) 0.0003(15) 0.0240(15) -0.0040(14) N11 0.0460(13) 0.0608(16) 0.0716(16) -0.0025(12) 0.0296(13) -0.0015(11) C40 0.0524(17) 0.071(2) 0.071(2) -0.0102(16) 0.0276(17) -0.0036(15) C41 0.067(2) 0.094(3) 0.077(2) -0.014(2) 0.0381(19) -0.0046(18) C42 0.093(3) 0.110(3) 0.082(3) -0.014(2) 0.044(2) -0.001(2) C43 0.116(3) 0.157(5) 0.096(3) -0.028(3) 0.063(3) -0.004(3) C28 0.0520(17) 0.063(2) 0.068(2) 0.0011(15) 0.0299(16) -0.0020(14) C29 0.0606(19) 0.069(2) 0.071(2) -0.0031(16) 0.0333(17) 0.0047(15) C30 0.079(2) 0.074(2) 0.088(2) 0.0006(19) 0.040(2) 0.0055(18) C31 0.098(3) 0.080(3) 0.130(4) 0.010(2) 0.045(3) 0.018(2) C32 0.0548(18) 0.075(2) 0.081(2) -0.0014(17) 0.0399(18) -0.0061(15) C33 0.074(2) 0.084(2) 0.081(2) -0.0066(19) 0.044(2) -0.0080(18) C34 0.100(3) 0.111(3) 0.097(3) -0.002(2) 0.064(3) -0.017(2) C35 0.155(5) 0.166(5) 0.102(4) -0.021(3) 0.087(4) -0.023(4) C36 0.0472(17) 0.071(2) 0.077(2) 0.0019(16) 0.0297(16) 0.0055(14) C37 0.0583(19) 0.073(2) 0.089(2) -0.0035(18) 0.0360(18) 0.0047(16) C38 0.082(2) 0.086(3) 0.091(3) 0.008(2) 0.051(2) 0.0188(19) C39 0.099(3) 0.094(3) 0.136(4) -0.002(3) 0.059(3) 0.025(2) F1 0.0590(10) 0.0647(11) 0.0641(10) 0.0009(8) 0.0306(8) -0.0029(8) O16 0.132(3) 0.283(5) 0.138(3) -0.063(3) 0.094(3) -0.062(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.233(4) . ? O2 N3 1.200(4) . ? O3 N3 1.203(4) . ? O4 N4 1.201(4) . ? O5 N4 1.208(4) . ? O6 C12 1.237(4) . ? O7 N6 1.215(4) . ? O8 N6 1.216(4) . ? O9 N7 1.216(5) . ? O10 N7 1.224(5) . ? O11 C21 1.233(3) . ? O12 N9 1.211(4) . ? O13 N9 1.212(4) . ? O14 N10 1.208(4) . ? O15 N10 1.213(3) . ? N1 C19 1.458(4) . ? N1 C1 1.459(4) . ? N1 C10 1.467(4) . ? N2 C3 1.318(4) . ? N2 C2 1.455(4) . ? N2 H2 0.8599 . ? N3 C6 1.469(4) . ? N4 C8 1.469(4) . ? N5 C12 1.338(4) . ? N5 C11 1.449(4) . ? N5 H5A 0.8600 . ? N6 C17 1.476(5) . ? N7 C15 1.474(5) . ? N8 C21 1.326(4) . ? N8 C20 1.452(4) . ? N8 H8A 0.8600 . ? N9 C24 1.477(4) . ? N10 C26 1.462(4) . ? C1 C2 1.514(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.524(4) . ? C4 C5 1.382(4) . ? C4 C9 1.390(4) . ? C5 C6 1.368(4) . ? C5 H5 0.9300 . ? C6 C7 1.367(4) . ? C7 C8 1.374(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(4) . ? C9 H9 0.9300 . ? C10 C11 1.509(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.502(5) . ? C13 C14 1.386(4) . ? C13 C18 1.388(4) . ? C18 C17 1.376(5) . ? C18 H18 0.9300 . ? C17 C16 1.380(5) . ? C16 C15 1.379(5) . ? C16 H16 0.9300 . ? C15 C14 1.359(5) . ? C14 H14 0.9300 . ? C19 C20 1.512(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.505(4) . ? C22 C27 1.387(4) . ? C22 C23 1.391(4) . ? C27 C26 1.381(4) . ? C27 H27 0.9300 . ? C26 C25 1.375(4) . ? C25 C24 1.367(4) . ? C25 H25 0.9300 . ? C24 C23 1.370(4) . ? C23 H23 0.9300 . ? N11 C32 1.509(4) . ? N11 C28 1.518(4) . ? N11 C40 1.527(4) . ? N11 C36 1.526(4) . ? C40 C41 1.502(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.509(5) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.496(6) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C28 C29 1.508(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.518(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.488(5) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.507(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.511(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.506(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C37 1.498(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.530(5) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.468(5) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? 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 C19 N1 C1 112.6(3) . . ? C19 N1 C10 113.3(3) . . ? C1 N1 C10 112.2(3) . . ? C3 N2 C2 121.8(3) . . ? C3 N2 H2 119.1 . . ? C2 N2 H2 119.1 . . ? O2 N3 O3 123.2(4) . . ? O2 N3 C6 118.3(3) . . ? O3 N3 C6 118.6(4) . . ? O4 N4 O5 122.4(3) . . ? O4 N4 C8 119.2(3) . . ? O5 N4 C8 118.4(3) . . ? C12 N5 C11 121.6(3) . . ? C12 N5 H5A 119.2 . . ? C11 N5 H5A 119.2 . . ? O7 N6 O8 123.6(4) . . ? O7 N6 C17 119.3(4) . . ? O8 N6 C17 117.1(4) . . ? O9 N7 O10 124.8(5) . . ? O9 N7 C15 118.8(5) . . ? O10 N7 C15 116.3(5) . . ? C21 N8 C20 121.3(3) . . ? C21 N8 H8A 119.4 . . ? C20 N8 H8A 119.3 . . ? O12 N9 O13 124.8(3) . . ? O12 N9 C24 117.7(3) . . ? O13 N9 C24 117.5(3) . . ? O14 N10 O15 122.8(3) . . ? O14 N10 C26 118.9(3) . . ? O15 N10 C26 118.2(3) . . ? N1 C1 C2 110.8(3) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 109.9(3) . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O1 C3 N2 124.8(3) . . ? O1 C3 C4 117.6(3) . . ? N2 C3 C4 117.7(3) . . ? C5 C4 C9 119.6(3) . . ? C5 C4 C3 115.9(3) . . ? C9 C4 C3 124.5(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 122.6(3) . . ? C7 C6 N3 119.3(3) . . ? C5 C6 N3 118.1(3) . . ? C6 C7 C8 116.6(3) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? C7 C8 C9 123.5(3) . . ? C7 C8 N4 117.9(3) . . ? C9 C8 N4 118.6(3) . . ? C8 C9 C4 118.0(3) . . ? C8 C9 H9 121.0 . . ? C4 C9 H9 121.0 . . ? N1 C10 C11 113.2(3) . . ? N1 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? N1 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? N5 C11 C10 111.5(3) . . ? N5 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? N5 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? O6 C12 N5 123.0(3) . . ? O6 C12 C13 119.4(3) . . ? N5 C12 C13 117.6(3) . . ? C14 C13 C18 119.0(3) . . ? C14 C13 C12 116.2(3) . . ? C18 C13 C12 124.7(3) . . ? C17 C18 C13 119.4(3) . . ? C17 C18 H18 120.3 . . ? C13 C18 H18 120.3 . . ? C18 C17 C16 122.4(4) . . ? C18 C17 N6 119.0(3) . . ? C16 C17 N6 118.6(4) . . ? C15 C16 C17 116.5(4) . . ? C15 C16 H16 121.8 . . ? C17 C16 H16 121.8 . . ? C14 C15 C16 123.0(3) . . ? C14 C15 N7 118.6(5) . . ? C16 C15 N7 118.4(4) . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? N1 C19 C20 112.0(3) . . ? N1 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? N1 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? N8 C20 C19 111.7(3) . . ? N8 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? N8 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? O11 C21 N8 123.5(3) . . ? O11 C21 C22 118.6(3) . . ? N8 C21 C22 117.8(3) . . ? C27 C22 C23 118.8(3) . . ? C27 C22 C21 124.6(3) . . ? C23 C22 C21 116.6(3) . . ? C26 C27 C22 118.8(3) . . ? C26 C27 H27 120.6 . . ? C22 C27 H27 120.6 . . ? C25 C26 C27 123.0(3) . . ? C25 C26 N10 118.2(3) . . ? C27 C26 N10 118.7(3) . . ? C24 C25 C26 117.0(3) . . ? C24 C25 H25 121.5 . . ? C26 C25 H25 121.5 . . ? C25 C24 C23 122.1(3) . . ? C25 C24 N9 118.3(3) . . ? C23 C24 N9 119.6(3) . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C32 N11 C28 111.1(2) . . ? C32 N11 C40 107.5(2) . . ? C28 N11 C40 111.3(2) . . ? C32 N11 C36 111.0(2) . . ? C28 N11 C36 105.9(2) . . ? C40 N11 C36 110.1(2) . . ? C41 C40 N11 115.6(3) . . ? C41 C40 H40A 108.4 . . ? N11 C40 H40A 108.4 . . ? C41 C40 H40B 108.4 . . ? N11 C40 H40B 108.4 . . ? H40A C40 H40B 107.4 . . ? C40 C41 C42 111.6(3) . . ? C40 C41 H41A 109.3 . . ? C42 C41 H41A 109.3 . . ? C40 C41 H41B 109.3 . . ? C42 C41 H41B 109.3 . . ? H41A C41 H41B 108.0 . . ? C43 C42 C41 113.7(4) . . ? C43 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? C43 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C29 C28 N11 117.9(2) . . ? C29 C28 H28A 107.8 . . ? N11 C28 H28A 107.8 . . ? C29 C28 H28B 107.8 . . ? N11 C28 H28B 107.8 . . ? H28A C28 H28B 107.2 . . ? C28 C29 C30 109.6(3) . . ? C28 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? C28 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? C31 C30 C29 115.0(3) . . ? C31 C30 H30A 108.5 . . ? C29 C30 H30A 108.5 . . ? C31 C30 H30B 108.5 . . ? C29 C30 H30B 108.5 . . ? H30A C30 H30B 107.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N11 C32 C33 115.7(3) . . ? N11 C32 H32A 108.4 . . ? C33 C32 H32A 108.4 . . ? N11 C32 H32B 108.4 . . ? C33 C32 H32B 108.4 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C34 112.7(3) . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? C35 C34 C33 111.2(3) . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34B 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 N11 117.5(3) . . ? C37 C36 H36A 107.9 . . ? N11 C36 H36A 107.9 . . ? C37 C36 H36B 107.9 . . ? N11 C36 H36B 107.9 . . ? H36A C36 H36B 107.2 . . ? C36 C37 C38 108.8(3) . . ? C36 C37 H37A 109.9 . . ? C38 C37 H37A 109.9 . . ? C36 C37 H37B 109.9 . . ? C38 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? C39 C38 C37 113.3(3) . . ? C39 C38 H38A 108.9 . . ? C37 C38 H38A 108.9 . . ? C39 C38 H38B 108.9 . . ? C37 C38 H38B 108.9 . . ? H38A C38 H38B 107.7 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.89 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.389 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.039 data_Amide(F)-DMF _database_code_depnum_ccdc_archive 'CCDC 803581' #TrackingRef '- All CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 N10 O15, C16 H36 N, C3 H7 N O, F' _chemical_formula_sum 'C46 H67 F N12 O16' _chemical_formula_weight 1063.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0759(3) _cell_length_b 16.7929(6) _cell_length_c 16.8986(5) _cell_angle_alpha 79.197(2) _cell_angle_beta 78.461(3) _cell_angle_gamma 89.753(2) _cell_volume 2750.23(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5367 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 22.53 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29276 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 28.39 _reflns_number_total 13732 _reflns_number_gt 11770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Appropriate bond restraints have been applied in SHELXL-97 to ensure standard bond geometry of lattice DMF molecule and tetrabutylammonium cation. ; _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^)+(0.0200P)^2^+0.0010P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13133 _refine_ls_number_parameters 683 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1917 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.1841 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.006 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 N1 N 0.6327(2) 0.27505(15) 0.38193(15) 0.0652(7) Uani 1 1 d . . . C4 C 0.9928(3) 0.38984(16) 0.51649(17) 0.0590(8) Uani 1 1 d . . . C8 C 1.1856(3) 0.43694(17) 0.41061(18) 0.0623(8) Uani 1 1 d . . . C9 C 1.0539(3) 0.40908(16) 0.43301(18) 0.0617(8) Uani 1 1 d . . . H9 H 1.0051 0.4029 0.3931 0.074 Uiso 1 1 calc R . . C3 C 0.8473(3) 0.36024(18) 0.5475(2) 0.0661(8) Uani 1 1 d . . . C6 C 1.2004(4) 0.42993(18) 0.5481(2) 0.0699(9) Uani 1 1 d . . . C7 C 1.2631(3) 0.44799(17) 0.4658(2) 0.0697(9) Uani 1 1 d . . . H7 H 1.3530 0.4666 0.4490 0.084 Uiso 1 1 calc R . . C5 C 1.0684(4) 0.40210(18) 0.57291(19) 0.0691(9) Uani 1 1 d . . . H5 H 1.0292 0.3913 0.6287 0.083 Uiso 1 1 calc R . . C2 C 0.6457(3) 0.3030(2) 0.5200(2) 0.0804(10) Uani 1 1 d . . . H2A H 0.5988 0.3305 0.5627 0.097 Uiso 1 1 calc R . . H2B H 0.6408 0.2453 0.5424 0.097 Uiso 1 1 calc R . . C1 C 0.5766(3) 0.3191(2) 0.4473(2) 0.0799(10) Uani 1 1 d . . . H1A H 0.4810 0.3042 0.4664 0.096 Uiso 1 1 calc R . . H1B H 0.5838 0.3768 0.4247 0.096 Uiso 1 1 calc R . . N3 N 1.2465(3) 0.45876(16) 0.32186(18) 0.0745(7) Uani 1 1 d . . . N2 N 0.7864(3) 0.33099(15) 0.49664(16) 0.0712(7) Uani 1 1 d . . . H2 H 0.8312 0.3284 0.4483 0.085 Uiso 1 1 calc R . . N4 N 1.2779(4) 0.44301(19) 0.6094(2) 0.0930(9) Uani 1 1 d . . . O1 O 0.7915(2) 0.36773(13) 0.61834(13) 0.0826(7) Uani 1 1 d . . . O2 O 1.1729(3) 0.45713(17) 0.27333(15) 0.1031(8) Uani 1 1 d . . . O3 O 1.3676(3) 0.47638(16) 0.30218(15) 0.1000(8) Uani 1 1 d . . . O4 O 1.3986(4) 0.45777(19) 0.5876(2) 0.1215(10) Uani 1 1 d . . . O5 O 1.2162(4) 0.4385(2) 0.6798(2) 0.1357(12) Uani 1 1 d . . . C13 C 1.0108(3) 0.2579(2) 0.15951(19) 0.0695(8) Uani 1 1 d . . . C12 C 0.8864(3) 0.3087(2) 0.1695(2) 0.0771(9) Uani 1 1 d . . . C17 C 1.2110(3) 0.2022(2) 0.1969(2) 0.0769(9) Uani 1 1 d . . . C18 C 1.1023(3) 0.2492(2) 0.21173(19) 0.0722(9) Uani 1 1 d . . . H18 H 1.0892 0.2754 0.2564 0.087 Uiso 1 1 calc R . . C10 C 0.6084(3) 0.3170(2) 0.3018(2) 0.0770(9) Uani 1 1 d . . . H10A H 0.5247 0.3460 0.3101 0.092 Uiso 1 1 calc R . . H10B H 0.5981 0.2773 0.2683 0.092 Uiso 1 1 calc R . . C11 C 0.7233(3) 0.3760(2) 0.2572(2) 0.0817(10) Uani 1 1 d . . . H11A H 0.7017 0.4052 0.2063 0.098 Uiso 1 1 calc R . . H11B H 0.7346 0.4153 0.2910 0.098 Uiso 1 1 calc R . . C15 C 1.1474(4) 0.1734(3) 0.0803(2) 0.0969(12) Uani 1 1 d . . . C14 C 1.0356(4) 0.2199(2) 0.0925(2) 0.0861(10) Uani 1 1 d . . . H14 H 0.9768 0.2257 0.0559 0.103 Uiso 1 1 calc R . . C16 C 1.2388(4) 0.1632(2) 0.1313(2) 0.0909(11) Uani 1 1 d . . . H16 H 1.3146 0.1318 0.1220 0.109 Uiso 1 1 calc R . . N5 N 0.8491(3) 0.33400(15) 0.23887(17) 0.0716(7) Uani 1 1 d . . . H5A H 0.9000 0.3256 0.2746 0.086 Uiso 1 1 calc R . . N6 N 1.3075(3) 0.1941(3) 0.2528(2) 0.0958(10) Uani 1 1 d . . . N7 N 1.1705(6) 0.1332(3) 0.0080(3) 0.1473(16) Uani 1 1 d . . . O6 O 0.8235(3) 0.32222(18) 0.11244(16) 0.1121(9) Uani 1 1 d . . . O7 O 1.3941(3) 0.1437(2) 0.2457(2) 0.1402(12) Uani 1 1 d . . . O8 O 1.2932(3) 0.2358(2) 0.3049(2) 0.1203(10) Uani 1 1 d . . . O10 O 1.0896(5) 0.1406(3) -0.0353(3) 0.204(2) Uani 1 1 d . . . O9 O 1.2690(6) 0.0959(4) -0.0051(3) 0.251(3) Uani 1 1 d . . . C21 C 0.8969(3) 0.07543(19) 0.37271(19) 0.0635(8) Uani 1 1 d . . . C20 C 0.6852(3) 0.13785(19) 0.3543(2) 0.0767(9) Uani 1 1 d . . . H20A H 0.6476 0.0829 0.3655 0.092 Uiso 1 1 calc R . . H20B H 0.6970 0.1586 0.2957 0.092 Uiso 1 1 calc R . . C19 C 0.5880(3) 0.19025(19) 0.4010(2) 0.0731(9) Uani 1 1 d . . . H19A H 0.4994 0.1857 0.3876 0.088 Uiso 1 1 calc R . . H19B H 0.5790 0.1702 0.4596 0.088 Uiso 1 1 calc R . . C22 C 1.0243(3) 0.07771(17) 0.40597(17) 0.0594(7) Uani 1 1 d . . . C23 C 1.1227(3) 0.02220(18) 0.38718(18) 0.0674(8) Uani 1 1 d . . . H23 H 1.1108 -0.0131 0.3527 0.081 Uiso 1 1 calc R . . C26 C 1.1604(3) 0.12260(19) 0.49089(19) 0.0694(8) Uani 1 1 d . . . C24 C 1.2373(3) 0.0195(2) 0.4195(2) 0.0709(9) Uani 1 1 d . . . C27 C 1.0439(3) 0.12790(18) 0.45911(19) 0.0668(8) Uani 1 1 d . . . H27 H 0.9790 0.1651 0.4734 0.080 Uiso 1 1 calc R . . C25 C 1.2601(3) 0.0691(2) 0.4719(2) 0.0762(9) Uani 1 1 d . . . H25 H 1.3384 0.0666 0.4934 0.091 Uiso 1 1 calc R . . N8 N 0.8162(2) 0.13737(15) 0.37844(15) 0.0693(7) Uani 1 1 d . . . H8 H 0.8415 0.1780 0.3967 0.083 Uiso 1 1 calc R . . N10 N 1.3400(3) -0.0402(2) 0.3990(2) 0.0940(9) Uani 1 1 d . . . N9 N 1.1791(5) 0.1754(2) 0.5482(2) 0.0982(10) Uani 1 1 d . . . O11 O 0.8705(2) 0.01583(14) 0.34567(15) 0.0834(7) Uani 1 1 d . . . O14 O 1.4462(3) -0.03690(18) 0.42139(19) 0.1190(10) Uani 1 1 d . . . O13 O 1.0793(4) 0.21139(18) 0.5774(2) 0.1251(11) Uani 1 1 d . . . O15 O 1.3133(3) -0.0898(2) 0.3612(3) 0.1468(14) Uani 1 1 d . . . O12 O 1.2904(4) 0.1785(2) 0.5658(2) 0.1354(12) Uani 1 1 d . . . N11 N 0.2551(3) 0.69520(18) 0.12782(16) 0.0857(9) Uani 1 1 d . . . C29 C 0.4092(4) 0.6362(2) 0.0144(2) 0.0925(11) Uani 1 1 d . . . H29A H 0.3459 0.5927 0.0148 0.111 Uiso 1 1 calc R . . H29B H 0.4660 0.6163 0.0534 0.111 Uiso 1 1 calc R . . C28 C 0.3332(4) 0.7060(2) 0.03965(19) 0.0818(10) Uani 1 1 d . . . H28A H 0.2696 0.7208 0.0036 0.098 Uiso 1 1 calc R . . H28B H 0.3970 0.7516 0.0301 0.098 Uiso 1 1 calc R . . C30 C 0.4964(4) 0.6601(2) -0.0706(2) 0.1023(12) Uani 1 1 d . . . H30A H 0.4385 0.6819 -0.1083 0.123 Uiso 1 1 calc R . . H30B H 0.5592 0.7035 -0.0698 0.123 Uiso 1 1 calc R . . C31 C 0.5753(5) 0.5944(3) -0.1032(3) 0.1400(18) Uani 1 1 d . . . H31A H 0.6281 0.5694 -0.0645 0.210 Uiso 1 1 calc R . . H31B H 0.6346 0.6168 -0.1545 0.210 Uiso 1 1 calc R . . H31C H 0.5144 0.5546 -0.1118 0.210 Uiso 1 1 calc R . . C32 C 0.1485(4) 0.6255(2) 0.1470(2) 0.1023(13) Uani 1 1 d . . . H32A H 0.1951 0.5760 0.1395 0.123 Uiso 1 1 calc R . . H32B H 0.1050 0.6187 0.2046 0.123 Uiso 1 1 calc R . . C33 C 0.0398(4) 0.6348(3) 0.0968(3) 0.1075(13) Uani 1 1 d . . . H33A H 0.0818 0.6465 0.0388 0.129 Uiso 1 1 calc R . . H33B H -0.0149 0.6804 0.1088 0.129 Uiso 1 1 calc R . . C34 C -0.0513(6) 0.5587(3) 0.1147(3) 0.1418(19) Uani 1 1 d . . . H34A H 0.0037 0.5134 0.1021 0.170 Uiso 1 1 calc R . . H34B H -0.0918 0.5467 0.1729 0.170 Uiso 1 1 calc R . . C35 C -0.1628(6) 0.5665(4) 0.0660(4) 0.177(3) Uani 1 1 d . . . H35A H -0.2171 0.6116 0.0776 0.266 Uiso 1 1 calc R . . H35B H -0.2186 0.5177 0.0812 0.266 Uiso 1 1 calc R . . H35C H -0.1235 0.5751 0.0083 0.266 Uiso 1 1 calc R . . C36 C 0.3479(5) 0.6727(3) 0.1875(2) 0.1026(13) Uani 1 1 d . . . H36A H 0.2940 0.6662 0.2429 0.123 Uiso 1 1 calc R . . H36B H 0.3846 0.6203 0.1808 0.123 Uiso 1 1 calc R . . C38 C 0.5508(6) 0.6943(4) 0.2402(3) 0.162(2) Uani 1 1 d D . . H38A H 0.4953 0.6829 0.2953 0.194 Uiso 1 1 calc R . . H38B H 0.5840 0.6432 0.2269 0.194 Uiso 1 1 calc R . . C37 C 0.4620(6) 0.7298(3) 0.1805(3) 0.1334(17) Uani 1 1 d . . . H37A H 0.4278 0.7811 0.1928 0.160 Uiso 1 1 calc R . . H37B H 0.5148 0.7396 0.1247 0.160 Uiso 1 1 calc R . . C39 C 0.6690(7) 0.7471(4) 0.2405(5) 0.215(3) Uani 1 1 d D . . H39A H 0.7232 0.7605 0.1859 0.322 Uiso 1 1 calc R . . H39B H 0.7226 0.7189 0.2771 0.322 Uiso 1 1 calc R . . H39C H 0.6373 0.7960 0.2586 0.322 Uiso 1 1 calc R . . C40 C 0.1898(4) 0.7760(2) 0.1360(2) 0.0906(11) Uani 1 1 d . . . H40A H 0.2608 0.8181 0.1203 0.109 Uiso 1 1 calc R . . H40B H 0.1305 0.7872 0.0968 0.109 Uiso 1 1 calc R . . C41 C 0.1085(5) 0.7825(3) 0.2202(2) 0.1310(17) Uani 1 1 d . . . H41A H 0.0416 0.7381 0.2389 0.157 Uiso 1 1 calc R . . H41B H 0.1685 0.7779 0.2590 0.157 Uiso 1 1 calc R . . C42 C 0.0375(6) 0.8623(4) 0.2183(3) 0.1418(18) Uani 1 1 d D . . H42A H -0.0318 0.8623 0.1858 0.170 Uiso 1 1 calc R . . H42B H -0.0083 0.8648 0.2740 0.170 Uiso 1 1 calc R . . C43 C 0.1239(7) 0.9376(4) 0.1849(4) 0.188(3) Uani 1 1 d D . . H43A H 0.1990 0.9360 0.2122 0.282 Uiso 1 1 calc R . . H43B H 0.0712 0.9840 0.1941 0.282 Uiso 1 1 calc R . . H43C H 0.1570 0.9413 0.1269 0.282 Uiso 1 1 calc R . . N12 N 0.6396(5) 0.0331(3) 0.1336(3) 0.1411(16) Uani 1 1 d D . . O16 O 0.5760(8) 0.1064(4) 0.0375(6) 0.314(5) Uani 1 1 d D . . C45 C 0.6328(12) -0.0285(5) 0.2046(4) 0.177(2) Uani 1 1 d D . . H45A H 0.5549 -0.0640 0.2103 0.475 Uiso 1 1 calc R . . H45B H 0.6239 -0.0045 0.2524 0.475 Uiso 1 1 calc R . . H45C H 0.7131 -0.0594 0.1988 0.475 Uiso 1 1 calc R . . C46 C 0.7575(8) 0.0837(7) 0.1206(7) 0.1397(18) Uani 1 1 d D . . H46A H 0.7994 0.0940 0.0632 0.502 Uiso 1 1 calc R . . H46B H 0.8200 0.0575 0.1522 0.502 Uiso 1 1 calc R . . H46C H 0.7327 0.1343 0.1374 0.502 Uiso 1 1 calc R . . C44 C 0.5579(12) 0.0360(4) 0.0790(7) 0.214(3) Uani 1 1 d D . . H44 H 0.5031 -0.0056 0.0726 0.634 Uiso 1 1 calc R . . F1 F 0.94870(15) 0.27969(9) 0.37190(9) 0.0660(5) 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 N1 0.0559(15) 0.0643(16) 0.0706(17) -0.0080(13) -0.0059(12) 0.0091(12) C4 0.073(2) 0.0511(17) 0.0507(18) -0.0079(13) -0.0080(16) 0.0102(15) C8 0.066(2) 0.0563(18) 0.059(2) -0.0077(14) -0.0024(16) 0.0077(15) C9 0.073(2) 0.0517(17) 0.0577(19) -0.0086(14) -0.0092(16) 0.0062(15) C3 0.077(2) 0.0591(19) 0.059(2) -0.0116(15) -0.0047(18) 0.0093(16) C6 0.086(3) 0.0600(19) 0.069(2) -0.0151(16) -0.025(2) 0.0181(17) C7 0.066(2) 0.0596(19) 0.086(3) -0.0176(17) -0.0161(19) 0.0117(15) C5 0.089(3) 0.0618(19) 0.0543(19) -0.0129(15) -0.0081(18) 0.0121(18) C2 0.074(2) 0.086(2) 0.072(2) -0.0159(18) 0.0079(18) 0.0002(18) C1 0.060(2) 0.082(2) 0.088(2) -0.0125(19) 0.0042(18) 0.0085(17) N3 0.080(2) 0.0701(18) 0.0648(19) -0.0051(14) -0.0007(17) 0.0054(15) N2 0.0646(17) 0.0836(18) 0.0599(16) -0.0206(14) 0.0070(13) -0.0032(14) N4 0.110(3) 0.092(2) 0.088(3) -0.0235(19) -0.037(2) 0.012(2) O1 0.0940(17) 0.0890(16) 0.0554(14) -0.0154(11) 0.0083(12) 0.0036(12) O2 0.106(2) 0.136(2) 0.0562(15) 0.0008(14) -0.0069(14) -0.0005(16) O3 0.0795(18) 0.110(2) 0.0949(18) -0.0161(14) 0.0161(14) -0.0006(15) O4 0.110(2) 0.136(3) 0.130(2) -0.0199(19) -0.056(2) -0.007(2) O5 0.157(3) 0.182(3) 0.089(2) -0.059(2) -0.045(2) 0.019(2) C13 0.062(2) 0.083(2) 0.057(2) -0.0061(17) -0.0039(16) 0.0010(17) C12 0.071(2) 0.092(2) 0.063(2) -0.0035(19) -0.0103(18) 0.0087(19) C17 0.058(2) 0.098(3) 0.065(2) -0.0017(19) -0.0047(17) -0.0007(19) C18 0.061(2) 0.094(2) 0.0560(19) -0.0091(17) -0.0011(16) -0.0030(18) C10 0.067(2) 0.079(2) 0.081(2) -0.0063(18) -0.0153(18) 0.0184(18) C11 0.088(2) 0.068(2) 0.082(2) -0.0038(18) -0.0117(19) 0.0204(19) C15 0.111(3) 0.119(3) 0.068(2) -0.035(2) -0.020(2) 0.033(3) C14 0.085(3) 0.103(3) 0.070(2) -0.015(2) -0.0171(19) 0.016(2) C16 0.083(3) 0.100(3) 0.084(3) -0.011(2) -0.009(2) 0.025(2) N5 0.0700(17) 0.0755(17) 0.0645(18) -0.0052(14) -0.0101(14) 0.0093(14) N6 0.059(2) 0.141(3) 0.078(2) -0.001(2) -0.0088(17) 0.006(2) N7 0.158(4) 0.190(4) 0.122(3) -0.076(3) -0.053(3) 0.080(3) O6 0.1005(19) 0.163(3) 0.0763(17) -0.0225(16) -0.0274(15) 0.0425(17) O7 0.101(2) 0.191(3) 0.130(3) -0.021(2) -0.0358(19) 0.060(2) O8 0.087(2) 0.180(3) 0.103(2) -0.032(2) -0.0334(17) 0.0091(19) O10 0.230(5) 0.289(6) 0.155(3) -0.139(4) -0.099(3) 0.125(4) O9 0.252(5) 0.363(7) 0.209(5) -0.184(5) -0.098(4) 0.205(6) C21 0.068(2) 0.0563(19) 0.0657(19) -0.0110(15) -0.0128(16) 0.0044(16) C20 0.069(2) 0.069(2) 0.099(3) -0.0202(18) -0.0287(19) 0.0118(17) C19 0.0571(19) 0.073(2) 0.087(2) -0.0060(17) -0.0188(17) 0.0017(16) C22 0.0624(19) 0.0512(17) 0.0607(18) -0.0041(14) -0.0095(15) 0.0059(14) C23 0.067(2) 0.0634(19) 0.068(2) -0.0096(15) -0.0081(16) 0.0042(16) C26 0.077(2) 0.062(2) 0.068(2) -0.0055(16) -0.0175(17) -0.0044(18) C24 0.057(2) 0.070(2) 0.079(2) -0.0042(18) -0.0059(17) 0.0055(16) C27 0.067(2) 0.0571(18) 0.073(2) -0.0051(16) -0.0138(17) 0.0108(15) C25 0.065(2) 0.079(2) 0.078(2) 0.0058(19) -0.0159(18) -0.0017(18) N8 0.0628(16) 0.0620(16) 0.0899(19) -0.0205(13) -0.0259(14) 0.0114(13) N10 0.071(2) 0.095(2) 0.109(3) -0.0081(19) -0.0124(19) 0.025(2) N9 0.121(3) 0.082(2) 0.098(2) -0.0097(19) -0.046(2) 0.002(2) O11 0.0826(16) 0.0768(15) 0.1019(18) -0.0330(13) -0.0301(13) 0.0154(12) O14 0.0717(17) 0.136(2) 0.142(2) -0.0073(18) -0.0229(17) 0.0297(16) O13 0.167(3) 0.107(2) 0.128(2) -0.0490(19) -0.071(2) 0.049(2) O15 0.123(3) 0.139(3) 0.209(4) -0.086(3) -0.058(3) 0.067(2) O12 0.117(2) 0.169(3) 0.140(3) -0.052(2) -0.051(2) -0.021(2) N11 0.103(2) 0.090(2) 0.0521(16) 0.0027(14) -0.0040(15) 0.0230(18) C29 0.108(3) 0.089(3) 0.068(2) -0.0042(19) 0.003(2) 0.010(2) C28 0.094(2) 0.089(2) 0.0493(19) -0.0006(17) 0.0037(17) 0.015(2) C30 0.106(3) 0.107(3) 0.082(3) -0.015(2) 0.004(2) 0.015(2) C31 0.164(5) 0.130(4) 0.113(4) -0.028(3) 0.007(3) 0.040(3) C32 0.123(3) 0.085(3) 0.072(2) 0.0114(19) 0.018(2) 0.009(2) C33 0.116(3) 0.101(3) 0.092(3) 0.001(2) -0.006(3) 0.007(3) C34 0.167(5) 0.114(4) 0.115(4) 0.005(3) 0.016(4) -0.039(4) C35 0.169(6) 0.195(6) 0.159(5) -0.021(4) -0.022(5) -0.058(5) C36 0.120(3) 0.119(3) 0.060(2) -0.002(2) -0.013(2) 0.024(3) C38 0.139(4) 0.218(7) 0.133(4) -0.021(4) -0.051(4) 0.022(5) C37 0.160(5) 0.149(4) 0.102(3) -0.021(3) -0.056(3) 0.033(4) C39 0.259(8) 0.158(6) 0.258(8) -0.009(5) -0.151(7) 0.008(6) C40 0.112(3) 0.088(3) 0.063(2) -0.0054(18) -0.005(2) 0.023(2) C41 0.164(4) 0.139(4) 0.075(3) -0.018(3) 0.007(3) 0.060(3) C42 0.154(5) 0.157(5) 0.101(4) -0.033(3) 0.013(3) 0.044(4) C43 0.225(7) 0.173(6) 0.171(6) -0.074(5) -0.015(5) 0.054(6) N12 0.151(4) 0.102(3) 0.152(4) -0.047(3) 0.035(3) -0.016(3) O16 0.276(8) 0.191(6) 0.429(11) 0.041(7) -0.055(8) -0.060(6) C45 0.169(6) 0.195(6) 0.160(5) -0.021(4) -0.023(5) -0.058(5) C46 0.163(4) 0.130(4) 0.114(4) -0.029(3) 0.006(3) 0.040(3) C44 0.252(8) 0.158(6) 0.261(8) -0.006(5) -0.152(7) 0.004(6) F1 0.0646(10) 0.0659(10) 0.0661(10) -0.0164(8) -0.0061(8) 0.0051(8) _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 N1 C19 1.453(4) . ? N1 C1 1.463(4) . ? N1 C10 1.471(4) . ? C4 C5 1.377(4) . ? C4 C9 1.399(4) . ? C4 C3 1.507(4) . ? C8 C9 1.364(4) . ? C8 C7 1.369(4) . ? C8 N3 1.479(4) . ? C3 O1 1.245(3) . ? C3 N2 1.315(4) . ? C6 C5 1.368(4) . ? C6 C7 1.385(5) . ? C6 N4 1.463(5) . ? C2 N2 1.449(4) . ? C2 C1 1.512(5) . ? N3 O2 1.215(3) . ? N3 O3 1.221(3) . ? N4 O4 1.211(4) . ? N4 O5 1.215(4) . ? C13 C14 1.382(5) . ? C13 C18 1.388(4) . ? C13 C12 1.513(5) . ? C12 O6 1.242(4) . ? C12 N5 1.306(4) . ? C17 C18 1.357(4) . ? C17 C16 1.374(5) . ? C17 N6 1.473(5) . ? C10 C11 1.507(4) . ? C11 N5 1.455(4) . ? C15 C14 1.371(5) . ? C15 C16 1.371(5) . ? C15 N7 1.482(5) . ? N6 O8 1.211(4) . ? N6 O7 1.217(4) . ? N7 O9 1.177(5) . ? N7 O10 1.192(5) . ? C21 O11 1.226(3) . ? C21 N8 1.323(4) . ? C21 C22 1.504(4) . ? C20 N8 1.457(4) . ? C20 C19 1.517(4) . ? C22 C27 1.383(4) . ? C22 C23 1.390(4) . ? C23 C24 1.370(4) . ? C26 C25 1.375(5) . ? C26 C27 1.381(4) . ? C26 N9 1.469(5) . ? C24 C25 1.375(5) . ? C24 N10 1.475(4) . ? N10 O15 1.203(4) . ? N10 O14 1.209(4) . ? N9 O12 1.220(4) . ? N9 O13 1.235(4) . ? N11 C36 1.506(5) . ? N11 C28 1.518(4) . ? N11 C40 1.522(4) . ? N11 C32 1.535(5) . ? C29 C28 1.481(4) . ? C29 C30 1.508(5) . ? C30 C31 1.483(5) . ? C32 C33 1.505(5) . ? C33 C34 1.524(6) . ? C34 C35 1.510(7) . ? C36 C37 1.472(6) . ? C38 C39 1.489(10) . ? C38 C37 1.519(6) . ? C40 C41 1.516(5) . ? C41 C42 1.515(6) . ? C42 C43 1.490(9) . ? N12 C44 1.350(12) . ? N12 C46 1.419(11) . ? N12 C45 1.419(9) . ? O16 C44 1.250(12) . ? 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 C19 N1 C1 112.9(2) . . ? C19 N1 C10 112.6(3) . . ? C1 N1 C10 111.3(2) . . ? C5 C4 C9 117.9(3) . . ? C5 C4 C3 118.5(3) . . ? C9 C4 C3 123.5(3) . . ? C9 C8 C7 123.5(3) . . ? C9 C8 N3 118.2(3) . . ? C7 C8 N3 118.3(3) . . ? C8 C9 C4 119.4(3) . . ? O1 C3 N2 124.4(3) . . ? O1 C3 C4 118.0(3) . . ? N2 C3 C4 117.6(3) . . ? C5 C6 C7 121.9(3) . . ? C5 C6 N4 119.8(3) . . ? C7 C6 N4 118.4(4) . . ? C8 C7 C6 116.3(3) . . ? C6 C5 C4 121.0(3) . . ? N2 C2 C1 111.3(3) . . ? N1 C1 C2 113.9(3) . . ? O2 N3 O3 124.3(3) . . ? O2 N3 C8 117.8(3) . . ? O3 N3 C8 117.9(3) . . ? C3 N2 C2 121.7(3) . . ? O4 N4 O5 123.8(4) . . ? O4 N4 C6 118.8(4) . . ? O5 N4 C6 117.4(4) . . ? C14 C13 C18 118.6(3) . . ? C14 C13 C12 117.1(3) . . ? C18 C13 C12 124.2(3) . . ? O6 C12 N5 123.7(3) . . ? O6 C12 C13 118.4(3) . . ? N5 C12 C13 117.9(3) . . ? C18 C17 C16 123.7(3) . . ? C18 C17 N6 118.6(4) . . ? C16 C17 N6 117.6(3) . . ? C17 C18 C13 119.4(3) . . ? N1 C10 C11 111.4(3) . . ? N5 C11 C10 110.9(3) . . ? C14 C15 C16 123.2(4) . . ? C14 C15 N7 118.1(4) . . ? C16 C15 N7 118.8(4) . . ? C15 C14 C13 119.5(3) . . ? C15 C16 C17 115.6(3) . . ? C12 N5 C11 121.6(3) . . ? O8 N6 O7 123.7(4) . . ? O8 N6 C17 118.2(4) . . ? O7 N6 C17 118.1(4) . . ? O9 N7 O10 122.2(5) . . ? O9 N7 C15 118.9(5) . . ? O10 N7 C15 118.9(4) . . ? O11 C21 N8 123.9(3) . . ? O11 C21 C22 119.1(3) . . ? N8 C21 C22 116.9(3) . . ? N8 C20 C19 110.6(3) . . ? N1 C19 C20 112.6(3) . . ? C27 C22 C23 118.4(3) . . ? C27 C22 C21 123.4(3) . . ? C23 C22 C21 118.1(3) . . ? C24 C23 C22 120.0(3) . . ? C25 C26 C27 122.8(3) . . ? C25 C26 N9 118.0(3) . . ? C27 C26 N9 119.1(3) . . ? C23 C24 C25 122.9(3) . . ? C23 C24 N10 119.0(3) . . ? C25 C24 N10 118.1(3) . . ? C26 C27 C22 119.7(3) . . ? C26 C25 C24 116.2(3) . . ? C21 N8 C20 121.2(3) . . ? O15 N10 O14 123.5(4) . . ? O15 N10 C24 118.2(4) . . ? O14 N10 C24 118.3(4) . . ? O12 N9 O13 124.6(4) . . ? O12 N9 C26 117.9(4) . . ? O13 N9 C26 117.5(4) . . ? C36 N11 C28 110.9(3) . . ? C36 N11 C40 111.6(3) . . ? C28 N11 C40 105.8(2) . . ? C36 N11 C32 106.0(3) . . ? C28 N11 C32 111.1(3) . . ? C40 N11 C32 111.6(3) . . ? C28 C29 C30 111.0(3) . . ? C29 C28 N11 117.5(3) . . ? C31 C30 C29 115.8(3) . . ? C33 C32 N11 116.5(3) . . ? C32 C33 C34 112.0(4) . . ? C35 C34 C33 113.3(4) . . ? C37 C36 N11 116.6(3) . . ? C39 C38 C37 114.9(5) . . ? C36 C37 C38 109.4(4) . . ? C41 C40 N11 116.6(3) . . ? C42 C41 C40 111.5(3) . . ? C43 C42 C41 116.8(5) . . ? C44 N12 C46 123.6(7) . . ? C44 N12 C45 124.6(7) . . ? C46 N12 C45 111.0(8) . . ? O16 C44 N12 104.8(8) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.538 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.040 data_Amide(F)-THF _database_code_depnum_ccdc_archive 'CCDC 803582' #TrackingRef '- All CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H84 F N11 O18' _chemical_formula_weight 1206.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 10.0221(9) _cell_length_b 33.279(3) _cell_length_c 19.4872(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.12(2) _cell_angle_gamma 90.00 _cell_volume 6499.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3577 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 17.84 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2576 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 88335 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.2113 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 24.84 _reflns_number_total 11125 _reflns_number_gt 9064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.Appropriate restraints have been applied in SHELXL to ensure standard bond geometry of lattice THF molecules and TBA cation. ; _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^)+(0.0250P)^2^+0.0010P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11178 _refine_ls_number_parameters 782 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.2386 _refine_ls_R_factor_gt 0.0835 _refine_ls_wR_factor_ref 0.1919 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.007 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 N1 N 1.3057(3) 0.59374(13) 0.7502(2) 0.0591(11) Uani 1 1 d . . . C4 C 0.9447(5) 0.51883(18) 0.8898(3) 0.0569(14) Uani 1 1 d . . . C6 C 0.7736(6) 0.5004(2) 0.9677(3) 0.0718(17) Uani 1 1 d . . . C5 C 0.8921(5) 0.49209(16) 0.9357(3) 0.0654(15) Uani 1 1 d . . . H5 H 0.9369 0.4683 0.9453 0.079 Uiso 1 1 calc R . . C9 C 0.8770(6) 0.55413(18) 0.8764(3) 0.0693(16) Uani 1 1 d . . . H9 H 0.9118 0.5726 0.8454 0.083 Uiso 1 1 calc R . . C1 C 1.3493(5) 0.55845(17) 0.7888(3) 0.0695(15) Uani 1 1 d . . . H1A H 1.3526 0.5651 0.8372 0.083 Uiso 1 1 calc R . . H1B H 1.4387 0.5511 0.7744 0.083 Uiso 1 1 calc R . . C2 C 1.2571(5) 0.52284(15) 0.7785(3) 0.0697(15) Uani 1 1 d . . . H2A H 1.2474 0.5176 0.7297 0.084 Uiso 1 1 calc R . . H2B H 1.2960 0.4992 0.7996 0.084 Uiso 1 1 calc R . . C3 C 1.0782(6) 0.50788(19) 0.8584(3) 0.0671(16) Uani 1 1 d . . . C8 C 0.7580(6) 0.56197(18) 0.9090(3) 0.0658(15) Uani 1 1 d . . . C7 C 0.7040(5) 0.5352(2) 0.9565(3) 0.0772(17) Uani 1 1 d . . . H7 H 0.6247 0.5407 0.9794 0.093 Uiso 1 1 calc R . . N2 N 1.1268(5) 0.53033(17) 0.8082(3) 0.0660(15) Uani 1 1 d . . . N3 N 0.7173(6) 0.47124(19) 1.0176(3) 0.0918(18) Uani 1 1 d . . . N4 N 0.6854(6) 0.59932(17) 0.8972(3) 0.0937(17) Uani 1 1 d . . . O1 O 1.1358(3) 0.47802(11) 0.8811(2) 0.0849(12) Uani 1 1 d . . . O3 O 0.7802(4) 0.44088(13) 1.0284(2) 0.1086(16) Uani 1 1 d . . . O5 O 0.5823(4) 0.60505(14) 0.9264(3) 0.1263(18) Uani 1 1 d . . . O2 O 0.6122(4) 0.47967(15) 1.0465(2) 0.1209(18) Uani 1 1 d . . . O4 O 0.7338(5) 0.62259(14) 0.8581(3) 0.148(2) Uani 1 1 d . . . F1 F 0.9921(2) 0.59471(7) 0.75077(12) 0.0638(8) Uani 1 1 d . . . C10 C 1.3459(5) 0.63131(16) 0.7839(3) 0.0712(16) Uani 1 1 d . . . H10A H 1.3470 0.6529 0.7504 0.085 Uiso 1 1 calc R . . H10B H 1.4355 0.6284 0.8020 0.085 Uiso 1 1 calc R . . C13 C 0.9438(6) 0.70075(18) 0.7955(3) 0.0673(16) Uani 1 1 d . . . C18 C 0.8689(6) 0.67695(15) 0.7522(3) 0.0632(15) Uani 1 1 d . . . H18 H 0.8959 0.6508 0.7425 0.076 Uiso 1 1 calc R . . C11 C 1.2502(6) 0.64225(15) 0.8423(3) 0.0772(17) Uani 1 1 d . . . H11A H 1.2410 0.6194 0.8729 0.093 Uiso 1 1 calc R . . H11B H 1.2872 0.6644 0.8684 0.093 Uiso 1 1 calc R . . C17 C 0.7554(6) 0.6918(2) 0.7237(3) 0.0742(17) Uani 1 1 d . . . C15 C 0.7826(7) 0.7526(2) 0.7784(4) 0.091(2) Uani 1 1 d . . . C12 C 1.0736(6) 0.6901(2) 0.8282(3) 0.0699(16) Uani 1 1 d . . . C16 C 0.7067(6) 0.7300(2) 0.7347(4) 0.091(2) Uani 1 1 d . . . H16 H 0.6292 0.7396 0.7141 0.109 Uiso 1 1 calc R . . C14 C 0.8967(6) 0.73975(19) 0.8081(3) 0.088(2) Uani 1 1 d . . . H14 H 0.9442 0.7568 0.8370 0.105 Uiso 1 1 calc R . . N5 N 1.1224(5) 0.65330(16) 0.8168(3) 0.0695(15) Uani 1 1 d . . . N7 N 0.6773(6) 0.6662(2) 0.6768(3) 0.0962(18) Uani 1 1 d . . . N6 N 0.7375(7) 0.7949(2) 0.7926(4) 0.136(3) Uani 1 1 d . . . O6 O 1.1300(4) 0.71552(11) 0.8641(2) 0.1012(14) Uani 1 1 d . . . O10 O 0.5742(5) 0.67830(14) 0.6518(3) 0.1311(19) Uani 1 1 d . . . O9 O 0.7187(4) 0.63220(16) 0.6648(3) 0.140(2) Uani 1 1 d . . . O7 O 0.8054(5) 0.81468(15) 0.8309(4) 0.179(3) Uani 1 1 d . . . O8 O 0.6368(5) 0.80618(15) 0.7642(4) 0.177(3) Uani 1 1 d . . . C22 C 0.9450(5) 0.55374(14) 0.5772(3) 0.0550(14) Uani 1 1 d . . . C24 C 0.7801(6) 0.51707(17) 0.5149(3) 0.0667(16) Uani 1 1 d . . . C23 C 0.8960(5) 0.53812(15) 0.5164(3) 0.0576(14) Uani 1 1 d . . . H23 H 0.9433 0.5421 0.4759 0.069 Uiso 1 1 calc R . . C25 C 0.7052(5) 0.50962(15) 0.5735(4) 0.0723(16) Uani 1 1 d . . . H25 H 0.6263 0.4950 0.5722 0.087 Uiso 1 1 calc R . . C21 C 1.0736(5) 0.57593(16) 0.5712(3) 0.0586(15) Uani 1 1 d . . . C27 C 0.8712(5) 0.54713(14) 0.6374(3) 0.0631(15) Uani 1 1 d . . . H27 H 0.9007 0.5574 0.6791 0.076 Uiso 1 1 calc R . . C19 C 1.3470(5) 0.59179(15) 0.6781(3) 0.0706(16) Uani 1 1 d . . . H19A H 1.3553 0.5639 0.6644 0.085 Uiso 1 1 calc R . . H19B H 1.4339 0.6043 0.6732 0.085 Uiso 1 1 calc R . . C26 C 0.7555(6) 0.52535(17) 0.6341(3) 0.0676(15) Uani 1 1 d . . . C20 C 1.2502(5) 0.61230(16) 0.6319(3) 0.0762(17) Uani 1 1 d . . . H20A H 1.2374 0.6396 0.6479 0.091 Uiso 1 1 calc R . . H20B H 1.2878 0.6136 0.5861 0.091 Uiso 1 1 calc R . . N8 N 1.1221(5) 0.59272(17) 0.6284(3) 0.0685(16) Uani 1 1 d . . . N10 N 0.7240(6) 0.50051(16) 0.4502(3) 0.0853(16) Uani 1 1 d . . . N9 N 0.6808(6) 0.51704(18) 0.6977(3) 0.1012(18) Uani 1 1 d . . . O11 O 1.1329(3) 0.57742(10) 0.51662(19) 0.0757(11) Uani 1 1 d . . . O14 O 0.7946(4) 0.50729(13) 0.3988(2) 0.1078(15) Uani 1 1 d . . . O15 O 0.6185(4) 0.48328(15) 0.4507(2) 0.1220(19) Uani 1 1 d . . . O13 O 0.5831(5) 0.49609(15) 0.6944(2) 0.1261(17) Uani 1 1 d . . . O12 O 0.7165(4) 0.53248(19) 0.7496(3) 0.162(3) Uani 1 1 d . . . N11 N 0.2417(6) 0.84739(19) 0.8641(3) 0.0938(16) Uani 1 1 d . . . C30 C 0.3255(7) 0.7708(3) 0.7219(4) 0.169(4) Uani 1 1 d D . . H30A H 0.3862 0.7879 0.6965 0.203 Uiso 1 1 calc R . . H30B H 0.3782 0.7543 0.7527 0.203 Uiso 1 1 calc R . . C28 C 0.3113(6) 0.8229(2) 0.8112(3) 0.117(2) Uani 1 1 d D . . H28A H 0.3744 0.8057 0.8349 0.140 Uiso 1 1 calc R . . H28B H 0.3630 0.8412 0.7830 0.140 Uiso 1 1 calc R . . C29 C 0.2311(6) 0.7968(2) 0.7639(4) 0.124(2) Uani 1 1 d D . . H29A H 0.1779 0.8135 0.7336 0.148 Uiso 1 1 calc R . . H29B H 0.1713 0.7800 0.7903 0.148 Uiso 1 1 calc R . . C34 C 0.0399(11) 0.7884(3) 1.0069(5) 0.213(5) Uani 1 1 d D . . H34A H 0.1019 0.7680 1.0228 0.255 Uiso 1 1 calc R . . H34B H -0.0193 0.7766 0.9730 0.255 Uiso 1 1 calc R . . C32 C 0.1827(9) 0.8138(3) 0.9123(6) 0.191(4) Uani 1 1 d D . . H32A H 0.1207 0.7982 0.8848 0.230 Uiso 1 1 calc R . . H32B H 0.2558 0.7960 0.9240 0.230 Uiso 1 1 calc R . . C35 C -0.0373(9) 0.8061(3) 1.0654(5) 0.221(5) Uani 1 1 d D . . H35A H 0.0222 0.8117 1.1028 0.332 Uiso 1 1 calc R . . H35B H -0.1043 0.7873 1.0802 0.332 Uiso 1 1 calc R . . H35C H -0.0792 0.8306 1.0508 0.332 Uiso 1 1 calc R . . C33 C 0.1125(12) 0.8239(3) 0.9779(5) 0.260(6) Uani 1 1 d D . . H33A H 0.0494 0.8455 0.9696 0.312 Uiso 1 1 calc R . . H33B H 0.1772 0.8334 1.0112 0.312 Uiso 1 1 calc R . . C31 C 0.2526(7) 0.7441(2) 0.6726(4) 0.181(3) Uani 1 1 d D . . H31A H 0.1946 0.7264 0.6975 0.271 Uiso 1 1 calc R . . H31B H 0.3159 0.7285 0.6469 0.271 Uiso 1 1 calc R . . H31C H 0.2008 0.7603 0.6417 0.271 Uiso 1 1 calc R . . C38 C 0.0303(11) 0.9401(3) 0.7909(7) 0.230(5) Uani 1 1 d D . . H38A H 0.0183 0.9602 0.8263 0.277 Uiso 1 1 calc R . . H38B H 0.0632 0.9530 0.7495 0.277 Uiso 1 1 calc R . . C37 C 0.1289(14) 0.9055(5) 0.8156(10) 0.369(12) Uani 1 1 d D . . H37A H 0.1852 0.9013 0.7758 0.442 Uiso 1 1 calc R . . H37B H 0.1852 0.9192 0.8486 0.442 Uiso 1 1 calc R . . C36 C 0.1181(12) 0.8640(3) 0.8453(8) 0.347(13) Uani 1 1 d D . . H36A H 0.0610 0.8650 0.8855 0.416 Uiso 1 1 calc R . . H36B H 0.0759 0.8466 0.8119 0.416 Uiso 1 1 calc R . . C42 C 0.5404(11) 0.9022(4) 0.9464(9) 0.321(10) Uani 1 1 d D . . H42A H 0.5619 0.9179 0.9060 0.385 Uiso 1 1 calc R . . H42B H 0.4931 0.9181 0.9804 0.385 Uiso 1 1 calc R . . C40 C 0.3420(9) 0.8728(2) 0.9049(4) 0.145(3) Uani 1 1 d D . . H40A H 0.3593 0.8963 0.8770 0.174 Uiso 1 1 calc R . . H40B H 0.2939 0.8822 0.9450 0.174 Uiso 1 1 calc R . . C41 C 0.4755(13) 0.8593(5) 0.9308(8) 0.380(12) Uani 1 1 d D . . H41A H 0.5251 0.8447 0.8962 0.456 Uiso 1 1 calc R . . H41B H 0.4677 0.8431 0.9720 0.456 Uiso 1 1 calc R . . C43 C 0.6542(11) 0.8780(3) 0.9744(6) 0.270(6) Uani 1 1 d D . . H43A H 0.6221 0.8521 0.9886 0.404 Uiso 1 1 calc R . . H43B H 0.6924 0.8917 1.0131 0.404 Uiso 1 1 calc R . . H43C H 0.7208 0.8746 0.9395 0.404 Uiso 1 1 calc R . . C39 C -0.0969(11) 0.9178(3) 0.7773(6) 0.264(6) Uani 1 1 d D . . H39A H -0.0840 0.8995 0.7399 0.396 Uiso 1 1 calc R . . H39B H -0.1660 0.9366 0.7658 0.396 Uiso 1 1 calc R . . H39C H -0.1223 0.9031 0.8177 0.396 Uiso 1 1 calc R . . O16 O 0.5658(11) 0.7566(3) 0.9178(6) 0.264(4) Uani 1 1 d . . . C44 C 0.5006(12) 0.7205(4) 0.9155(8) 0.230(5) Uani 1 1 d . . . H44A H 0.5530 0.7012 0.8898 0.276 Uiso 1 1 calc R . . H44B H 0.4153 0.7238 0.8926 0.276 Uiso 1 1 calc R . . C45 C 0.4805(17) 0.7065(4) 0.9829(9) 0.296(9) Uani 1 1 d . . . H45A H 0.5313 0.6823 0.9919 0.356 Uiso 1 1 calc R . . H45B H 0.3868 0.7016 0.9922 0.356 Uiso 1 1 calc R . . C46 C 0.531(2) 0.7410(8) 1.0233(13) 0.50(2) Uani 1 1 d . . . H46A H 0.4717 0.7639 1.0225 0.597 Uiso 1 1 calc R . . H46B H 0.5533 0.7338 1.0702 0.597 Uiso 1 1 calc R . . C47 C 0.6410(13) 0.7463(6) 0.9835(11) 0.401(14) Uani 1 1 d . . . H47A H 0.6937 0.7220 0.9791 0.482 Uiso 1 1 calc R . . H47B H 0.6967 0.7682 0.9993 0.482 Uiso 1 1 calc R . . O17 O 0.4296(13) 0.8946(3) 0.7042(6) 0.311(6) Uani 1 1 d . . . C48 C 0.5602(13) 0.9136(4) 0.6959(8) 0.330(11) Uani 1 1 d D . . H48A H 0.5587 0.9428 0.6968 0.396 Uiso 1 1 calc R . . H48B H 0.6294 0.9029 0.7255 0.396 Uiso 1 1 calc R . . C50 C 0.457(2) 0.9272(5) 0.6105(9) 0.377(11) Uani 1 1 d D . . H50A H 0.4818 0.9541 0.6247 0.453 Uiso 1 1 calc R . . H50B H 0.4319 0.9267 0.5624 0.453 Uiso 1 1 calc R . . C49 C 0.5569(19) 0.8965(6) 0.6287(8) 0.453(16) Uani 1 1 d . . . H49A H 0.5232 0.8692 0.6273 0.543 Uiso 1 1 calc R . . H49B H 0.6403 0.8988 0.6037 0.543 Uiso 1 1 calc R . . C51 C 0.3674(13) 0.9093(7) 0.6524(9) 0.353(12) Uani 1 1 d . . . H51A H 0.3020 0.9289 0.6677 0.423 Uiso 1 1 calc R . . H51B H 0.3211 0.8881 0.6280 0.423 Uiso 1 1 calc R . . O18 O 1.013(2) 0.8570(6) 0.5098(8) 0.381(8) Uani 1 1 d . . . C54 C 1.077(2) 0.8389(8) 0.583(2) 0.44(2) Uani 1 1 d . . . H54A H 1.1201 0.8131 0.5767 0.527 Uiso 1 1 calc R . . H54B H 1.1361 0.8577 0.6053 0.527 Uiso 1 1 calc R . . C55 C 0.913(3) 0.8230(8) 0.546(2) 0.487(19) Uani 1 1 d . . . H55A H 0.8238 0.8126 0.5385 0.585 Uiso 1 1 calc R . . H55B H 0.9823 0.8105 0.5191 0.585 Uiso 1 1 calc R . . C52 C 0.927(3) 0.8705(4) 0.5630(15) 0.386(15) Uani 1 1 d . . . H52A H 0.8537 0.8877 0.5498 0.463 Uiso 1 1 calc R . . H52B H 0.9687 0.8778 0.6063 0.463 Uiso 1 1 calc R . . C53 C 0.947(3) 0.8357(9) 0.6164(9) 0.335(13) Uani 1 1 d . . . H53A H 0.9079 0.8609 0.6311 0.402 Uiso 1 1 calc R . . H53B H 0.9402 0.8149 0.6512 0.402 Uiso 1 1 calc R . . H5N H 1.066(4) 0.6405(13) 0.792(2) 0.057(18) Uiso 1 1 d . . . H8N H 1.081(3) 0.5925(12) 0.6567(18) 0.005(14) Uiso 1 1 d . . . H2N H 1.081(4) 0.5450(12) 0.795(2) 0.030(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.075(3) 0.046(3) 0.056(3) 0.000(3) 0.009(2) -0.004(2) C4 0.068(4) 0.051(4) 0.051(4) 0.002(3) 0.004(3) -0.008(3) C6 0.080(5) 0.078(5) 0.057(4) 0.031(4) 0.004(3) -0.021(4) C5 0.074(4) 0.061(4) 0.061(4) 0.014(3) 0.002(3) -0.010(3) C9 0.076(4) 0.069(5) 0.063(4) 0.010(3) 0.017(3) -0.013(4) C1 0.080(4) 0.066(4) 0.062(4) -0.005(4) 0.003(3) 0.009(3) C2 0.101(4) 0.043(4) 0.065(4) 0.007(3) 0.017(3) 0.008(3) C3 0.095(5) 0.048(4) 0.059(4) 0.001(4) 0.002(4) 0.000(4) C8 0.077(4) 0.063(5) 0.057(4) 0.012(4) 0.004(3) -0.008(4) C7 0.084(4) 0.078(5) 0.069(5) 0.009(4) 0.007(3) -0.003(4) N2 0.073(4) 0.056(4) 0.068(4) 0.006(3) 0.012(3) 0.009(3) N3 0.093(5) 0.099(5) 0.084(4) 0.036(4) 0.001(3) -0.024(4) N4 0.113(5) 0.074(5) 0.094(5) 0.027(4) 0.031(4) 0.010(4) O1 0.104(3) 0.056(3) 0.094(3) 0.027(2) 0.015(2) 0.006(2) O3 0.142(4) 0.079(3) 0.105(4) 0.034(3) 0.019(3) -0.013(3) O5 0.109(3) 0.117(4) 0.153(5) 0.022(3) 0.059(3) 0.031(3) O2 0.084(3) 0.167(5) 0.112(4) 0.062(3) 0.015(3) -0.023(3) O4 0.165(4) 0.094(4) 0.184(6) 0.070(4) 0.089(4) 0.053(3) F1 0.0861(18) 0.0515(18) 0.0536(18) -0.0034(15) 0.0080(14) -0.0043(15) C10 0.082(4) 0.057(4) 0.075(4) -0.001(3) -0.011(3) -0.005(3) C13 0.076(4) 0.045(4) 0.081(5) -0.004(4) 0.013(4) -0.008(4) C18 0.077(4) 0.044(4) 0.069(4) 0.009(3) 0.010(3) -0.006(4) C11 0.098(5) 0.057(4) 0.077(5) -0.020(3) -0.007(4) 0.002(3) C17 0.074(5) 0.062(5) 0.086(5) -0.006(4) -0.001(4) -0.016(4) C15 0.094(6) 0.040(5) 0.140(7) -0.017(4) 0.006(5) 0.008(4) C12 0.084(5) 0.058(5) 0.068(5) -0.002(4) 0.009(4) -0.001(4) C16 0.088(5) 0.059(5) 0.124(6) 0.010(4) 0.008(4) 0.010(4) C14 0.078(5) 0.058(5) 0.127(6) -0.013(4) 0.003(4) 0.001(4) N5 0.072(4) 0.051(4) 0.085(4) -0.017(3) -0.015(3) 0.006(3) N7 0.093(5) 0.078(5) 0.118(5) 0.004(4) -0.012(4) 0.008(4) N6 0.084(5) 0.084(7) 0.242(9) -0.020(5) -0.005(5) 0.005(4) O6 0.125(3) 0.056(3) 0.122(4) -0.030(3) -0.024(3) -0.005(2) O10 0.111(4) 0.107(4) 0.175(5) -0.009(3) -0.048(3) 0.011(3) O9 0.140(4) 0.100(4) 0.181(5) -0.042(4) -0.063(3) 0.021(3) O7 0.153(5) 0.067(4) 0.316(9) -0.066(4) -0.047(5) 0.015(3) O8 0.123(4) 0.093(4) 0.316(9) -0.032(4) -0.038(5) 0.033(3) C22 0.066(4) 0.043(4) 0.056(4) -0.002(3) -0.002(3) 0.008(3) C24 0.067(4) 0.075(4) 0.058(4) -0.019(4) -0.004(4) 0.022(3) C23 0.055(4) 0.061(4) 0.057(4) 0.000(3) -0.004(3) 0.008(3) C25 0.066(4) 0.062(4) 0.089(5) -0.012(4) -0.004(4) 0.002(3) C21 0.076(4) 0.047(4) 0.053(4) 0.000(3) -0.001(4) 0.005(3) C27 0.074(4) 0.055(4) 0.060(4) -0.012(3) -0.003(3) -0.003(3) C19 0.081(4) 0.067(4) 0.064(4) -0.003(3) 0.014(3) -0.025(3) C26 0.074(4) 0.068(4) 0.060(5) -0.010(4) 0.006(4) -0.006(3) C20 0.075(4) 0.078(4) 0.075(5) 0.018(4) -0.007(3) -0.029(3) N8 0.075(4) 0.074(4) 0.056(4) 0.006(3) 0.011(4) -0.009(3) N10 0.093(5) 0.092(4) 0.070(4) -0.023(4) -0.007(4) 0.024(3) N9 0.096(5) 0.125(5) 0.083(5) -0.016(4) 0.023(4) -0.038(4) O11 0.098(3) 0.079(3) 0.050(3) 0.001(2) 0.022(2) -0.015(2) O14 0.144(4) 0.112(4) 0.067(3) -0.023(3) -0.004(3) -0.004(3) O15 0.073(3) 0.168(5) 0.125(4) -0.068(3) -0.009(3) -0.011(3) O13 0.120(4) 0.160(5) 0.099(4) -0.010(3) 0.032(3) -0.054(3) O12 0.133(4) 0.283(7) 0.072(4) -0.039(4) 0.029(3) -0.093(4) N11 0.095(4) 0.082(4) 0.104(5) -0.016(4) 0.036(4) -0.011(4) C30 0.147(7) 0.165(8) 0.195(9) -0.108(7) 0.016(6) -0.007(6) C28 0.116(5) 0.106(6) 0.128(6) -0.044(5) 0.036(5) -0.003(4) C29 0.132(6) 0.103(6) 0.136(7) -0.023(5) 0.003(5) -0.013(5) C34 0.283(12) 0.177(10) 0.178(11) -0.014(9) 0.062(9) -0.086(9) C32 0.171(8) 0.214(12) 0.189(11) -0.096(10) 0.012(8) -0.046(8) C35 0.257(10) 0.196(10) 0.210(12) -0.063(9) 0.069(9) -0.029(8) C33 0.318(15) 0.261(16) 0.201(14) -0.099(14) -0.010(11) -0.061(12) C31 0.244(9) 0.129(8) 0.169(9) -0.011(7) 0.011(7) -0.010(6) C38 0.282(15) 0.172(12) 0.237(14) 0.011(10) -0.009(11) 0.050(10) C37 0.281(16) 0.32(2) 0.50(3) 0.22(2) -0.058(15) -0.019(17) C36 0.220(14) 0.292(18) 0.53(3) -0.31(2) -0.091(17) 0.121(14) C42 0.255(14) 0.136(11) 0.57(3) -0.101(15) 0.162(15) 0.013(10) C40 0.194(8) 0.081(6) 0.159(8) -0.063(6) 0.076(7) -0.052(6) C41 0.34(2) 0.29(2) 0.51(3) -0.188(19) 0.049(19) 0.137(16) C43 0.347(16) 0.114(9) 0.347(17) -0.098(10) -0.003(13) -0.082(10) C39 0.354(16) 0.177(12) 0.261(14) 0.042(10) -0.107(13) 0.006(10) O16 0.333(10) 0.138(6) 0.321(13) 0.048(7) -0.006(9) -0.081(7) C44 0.315(13) 0.119(10) 0.255(17) -0.008(11) 0.003(12) -0.079(9) C45 0.49(2) 0.203(15) 0.200(16) 0.057(13) 0.093(16) -0.083(13) C46 0.62(4) 0.50(3) 0.38(3) -0.31(3) 0.19(3) -0.15(3) C47 0.212(13) 0.59(3) 0.40(3) 0.00(2) -0.230(17) -0.074(16) O17 0.323(13) 0.364(12) 0.245(11) 0.192(10) 0.011(9) -0.072(10) C48 0.197(12) 0.265(16) 0.53(3) -0.13(2) 0.011(17) -0.124(12) C50 0.303(18) 0.43(2) 0.40(3) 0.32(2) 0.011(19) 0.045(15) C49 0.52(3) 0.66(4) 0.170(14) 0.092(18) 0.167(16) 0.41(3) C51 0.191(13) 0.64(4) 0.232(17) 0.24(2) 0.039(11) -0.017(17) O18 0.48(2) 0.382(19) 0.277(15) -0.023(14) 0.117(15) -0.075(19) C54 0.31(2) 0.40(3) 0.60(5) 0.04(3) -0.28(3) 0.13(2) C55 0.48(4) 0.31(3) 0.67(6) -0.15(3) 0.02(4) -0.21(3) C52 0.62(4) 0.159(14) 0.38(3) 0.034(18) 0.26(3) 0.142(19) C53 0.57(4) 0.29(2) 0.143(13) 0.088(14) 0.07(2) 0.02(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.462(5) . ? N1 C19 1.466(6) . ? N1 C10 1.469(5) . ? C4 C5 1.368(6) . ? C4 C9 1.381(6) . ? C4 C3 1.516(7) . ? C6 C7 1.370(6) . ? C6 C5 1.370(6) . ? C6 N3 1.484(7) . ? C9 C8 1.376(6) . ? C1 C2 1.516(6) . ? C2 N2 1.450(6) . ? C3 O1 1.232(5) . ? C3 N2 1.323(7) . ? C8 C7 1.394(7) . ? C8 N4 1.458(7) . ? N3 O3 1.209(5) . ? N3 O2 1.228(5) . ? N4 O4 1.189(5) . ? N4 O5 1.195(5) . ? C10 C11 1.532(6) . ? C13 C18 1.380(6) . ? C13 C14 1.403(6) . ? C13 C12 1.491(7) . ? C18 C17 1.359(6) . ? C11 N5 1.423(6) . ? C17 C16 1.379(7) . ? C17 N7 1.476(7) . ? C15 C14 1.351(7) . ? C15 C16 1.366(7) . ? C15 N6 1.505(8) . ? C12 O6 1.234(6) . ? C12 N5 1.338(6) . ? N7 O10 1.212(5) . ? N7 O9 1.226(5) . ? N6 O7 1.205(7) . ? N6 O8 1.210(6) . ? C22 C23 1.384(6) . ? C22 C27 1.404(6) . ? C22 C21 1.490(6) . ? C24 C23 1.357(6) . ? C24 C25 1.389(7) . ? C24 N10 1.486(7) . ? C25 C26 1.386(7) . ? C21 O11 1.219(5) . ? C21 N8 1.338(7) . ? C27 C26 1.370(6) . ? C19 C20 1.489(6) . ? C26 N9 1.475(7) . ? C20 N8 1.441(6) . ? N10 O15 1.203(5) . ? N10 O14 1.247(5) . ? N9 O12 1.189(6) . ? N9 O13 1.204(5) . ? N11 C36 1.405(11) . ? N11 C28 1.488(7) . ? N11 C40 1.535(8) . ? N11 C32 1.574(12) . ? C30 C31 1.499(11) . ? C30 C29 1.522(8) . ? C28 C29 1.500(9) . ? C34 C33 1.498(15) . ? C34 C35 1.498(14) . ? C32 C33 1.497(15) . ? C38 C39 1.499(15) . ? C38 C37 1.592(15) . ? C37 C36 1.50(2) . ? C42 C43 1.499(17) . ? C42 C41 1.598(15) . ? C40 C41 1.499(16) . ? O16 C44 1.366(9) . ? O16 C47 1.524(16) . ? C44 C45 1.409(13) . ? C45 C46 1.48(2) . ? C46 C47 1.36(3) . ? O17 C51 1.283(13) . ? O17 C48 1.463(11) . ? C48 C49 1.429(19) . ? C50 C51 1.35(3) . ? C50 C49 1.471(17) . ? O18 C52 1.420(16) . ? O18 C54 1.67(3) . ? C54 C53 1.46(3) . ? C55 C53 1.47(3) . ? C55 C52 1.62(2) . ? 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 C1 N1 C19 112.0(4) . . ? C1 N1 C10 111.8(4) . . ? C19 N1 C10 112.9(4) . . ? C5 C4 C9 119.2(5) . . ? C5 C4 C3 116.6(6) . . ? C9 C4 C3 124.2(6) . . ? C7 C6 C5 122.6(5) . . ? C7 C6 N3 117.7(6) . . ? C5 C6 N3 119.7(6) . . ? C4 C5 C6 120.0(5) . . ? C8 C9 C4 120.0(5) . . ? N1 C1 C2 112.2(4) . . ? N2 C2 C1 111.2(4) . . ? O1 C3 N2 123.3(6) . . ? O1 C3 C4 117.6(6) . . ? N2 C3 C4 119.2(6) . . ? C9 C8 C7 121.5(6) . . ? C9 C8 N4 121.4(6) . . ? C7 C8 N4 117.1(6) . . ? C6 C7 C8 116.7(6) . . ? C3 N2 C2 122.0(6) . . ? O3 N3 O2 123.9(6) . . ? O3 N3 C6 117.6(6) . . ? O2 N3 C6 118.5(6) . . ? O4 N4 O5 123.6(6) . . ? O4 N4 C8 116.9(6) . . ? O5 N4 C8 119.5(6) . . ? N1 C10 C11 111.3(4) . . ? C18 C13 C14 117.1(6) . . ? C18 C13 C12 126.9(6) . . ? C14 C13 C12 116.0(6) . . ? C17 C18 C13 119.8(5) . . ? N5 C11 C10 111.4(5) . . ? C18 C17 C16 124.7(6) . . ? C18 C17 N7 119.1(6) . . ? C16 C17 N7 116.2(7) . . ? C14 C15 C16 124.4(6) . . ? C14 C15 N6 118.1(7) . . ? C16 C15 N6 117.5(7) . . ? O6 C12 N5 123.7(6) . . ? O6 C12 C13 118.6(6) . . ? N5 C12 C13 117.7(6) . . ? C15 C16 C17 114.0(6) . . ? C15 C14 C13 120.1(6) . . ? C12 N5 C11 120.5(5) . . ? O10 N7 O9 121.3(6) . . ? O10 N7 C17 120.6(6) . . ? O9 N7 C17 118.1(6) . . ? O7 N6 O8 125.8(8) . . ? O7 N6 C15 117.1(7) . . ? O8 N6 C15 117.2(7) . . ? C23 C22 C27 118.0(5) . . ? C23 C22 C21 115.3(5) . . ? C27 C22 C21 126.8(5) . . ? C23 C24 C25 122.4(6) . . ? C23 C24 N10 122.3(6) . . ? C25 C24 N10 115.3(6) . . ? C24 C23 C22 121.1(5) . . ? C26 C25 C24 115.9(5) . . ? O11 C21 N8 122.1(6) . . ? O11 C21 C22 120.7(6) . . ? N8 C21 C22 117.1(6) . . ? C26 C27 C22 119.3(5) . . ? N1 C19 C20 112.0(4) . . ? C27 C26 C25 123.2(6) . . ? C27 C26 N9 119.3(6) . . ? C25 C26 N9 117.4(6) . . ? N8 C20 C19 113.7(4) . . ? C21 N8 C20 123.5(5) . . ? O15 N10 O14 126.2(6) . . ? O15 N10 C24 120.2(6) . . ? O14 N10 C24 113.6(6) . . ? O12 N9 O13 122.7(6) . . ? O12 N9 C26 118.8(6) . . ? O13 N9 C26 118.5(6) . . ? C36 N11 C28 116.7(7) . . ? C36 N11 C40 119.7(7) . . ? C28 N11 C40 110.7(5) . . ? C36 N11 C32 96.0(7) . . ? C28 N11 C32 101.6(6) . . ? C40 N11 C32 109.1(6) . . ? C31 C30 C29 112.4(6) . . ? N11 C28 C29 119.4(6) . . ? C28 C29 C30 109.1(6) . . ? C33 C34 C35 103.1(8) . . ? C33 C32 N11 121.7(8) . . ? C32 C33 C34 111.8(9) . . ? C39 C38 C37 103.0(10) . . ? C36 C37 C38 137.5(12) . . ? N11 C36 C37 113.6(12) . . ? C43 C42 C41 84.1(8) . . ? C41 C40 N11 126.6(9) . . ? C40 C41 C42 99.3(10) . . ? C44 O16 C47 93.9(10) . . ? O16 C44 C45 109.1(13) . . ? C44 C45 C46 101.0(16) . . ? C47 C46 C45 94.4(15) . . ? C46 C47 O16 96.3(14) . . ? C51 O17 C48 100.5(12) . . ? C49 C48 O17 84.8(12) . . ? C51 C50 C49 90.1(12) . . ? C48 C49 C50 87.7(9) . . ? O17 C51 C50 108.6(15) . . ? C52 O18 C54 74.0(15) . . ? C53 C54 O18 94.1(13) . . ? C53 C55 C52 60.9(14) . . ? O18 C52 C55 66.4(16) . . ? C54 C53 C55 79(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.84 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.547 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.059