# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Nikitin, Kirill' _publ_contact_author_email kirill.nikitin@ucd.ie _publ_section_title ; Encapsulation of 4,4=E2=80=99-bipyridinium cations by two= crown ether molecules: formation and structure of [3]pseudorotaxanes ; loop_ _publ_author_name K.Nikitin H.Muller-Bunz data_fma19 _database_code_depnum_ccdc_archive 'CCDC 721642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2 (C24 H32 O8), C14 H18 N2, 2 (F6 P), 0.58 (H2 O)' _chemical_formula_sum 'C62 H83.16 N2 O16.58 F12 P2' _chemical_formula_weight 1411.92 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.7147(17) _cell_length_b 29.563(4) _cell_length_c 16.500(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6689.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9747 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.43 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 1.20 _exptl_crystal_size_min 0.80 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3196.8 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7326 _exptl_absorpt_correction_T_max 0.8740 _exptl_absorpt_process_details SADABS _exptl_special_details ; Hydrogen atoms of the solvent water could not be detected. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 107705 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.53 _reflns_number_total 8182 _reflns_number_gt 7319 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1086P)^2^+10.6199P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8182 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1947 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.78697(14) 0.13899(7) 0.21001(12) 0.0192(4) Uani 1 1 d . . . H1 H 0.7458 0.1533 0.1715 0.023 Uiso 1 1 calc R . . C2 C 0.88630(14) 0.13799(7) 0.19746(12) 0.0186(4) Uani 1 1 d . . . H2 H 0.9135 0.1506 0.1495 0.022 Uiso 1 1 calc R . . C3 C 0.94638(13) 0.11838(6) 0.25559(12) 0.0157(4) Uani 1 1 d . . . C4 C 0.90435(14) 0.09958(7) 0.32470(12) 0.0195(4) Uani 1 1 d . . . H4 H 0.9442 0.0864 0.3654 0.023 Uiso 1 1 calc R . . C5 C 0.80443(14) 0.10036(7) 0.33337(12) 0.0199(4) Uani 1 1 d . . . H5 H 0.7752 0.0871 0.3798 0.024 Uiso 1 1 calc R . . N N 0.74799(12) 0.11980(5) 0.27644(11) 0.0172(3) Uani 1 1 d . . . C6 C 0.64001(14) 0.12090(7) 0.28825(14) 0.0221(4) Uani 1 1 d . . . H6A H 0.6193 0.0942 0.3201 0.027 Uiso 1 1 calc R . . H6B H 0.6071 0.1197 0.2349 0.027 Uiso 1 1 calc R . . C7 C 0.61057(15) 0.16366(7) 0.33229(13) 0.0234(4) Uani 1 1 d . . . H7A H 0.6437 0.1649 0.3849 0.035 Uiso 1 1 calc R . . H7B H 0.5398 0.1637 0.3407 0.035 Uiso 1 1 calc R . . H7C H 0.6291 0.1900 0.2998 0.035 Uiso 1 1 calc R . . C8 C 0.73182(16) 0.06425(7) 0.07907(14) 0.0238(4) Uani 1 1 d . . . C9 C 0.79162(18) 0.07259(8) 0.01272(15) 0.0304(5) Uani 1 1 d . . . H9 H 0.7698 0.0919 -0.0296 0.037 Uiso 1 1 calc R . . C10 C 0.8839(2) 0.05264(9) 0.00815(16) 0.0358(6) Uani 1 1 d . . . H10 H 0.9250 0.0587 -0.0369 0.043 Uiso 1 1 calc R . . C11 C 0.91543(18) 0.02416(9) 0.06900(17) 0.0353(5) Uani 1 1 d . . . H11 H 0.9784 0.0109 0.0658 0.042 Uiso 1 1 calc R . . C12 C 0.85540(17) 0.01465(8) 0.13517(15) 0.0290(5) Uani 1 1 d . . . H12 H 0.8771 -0.0054 0.1764 0.035 Uiso 1 1 calc R . . C13 C 0.76375(16) 0.03458(7) 0.14063(13) 0.0233(4) Uani 1 1 d . . . O1 O 0.70014(12) 0.02732(5) 0.20326(10) 0.0257(3) Uani 1 1 d . . . C14 C 0.72233(19) -0.01038(7) 0.25535(15) 0.0290(5) Uani 1 1 d . . . H14A H 0.7881 -0.0066 0.2791 0.035 Uiso 1 1 calc R . . H14B H 0.7213 -0.0389 0.2239 0.035 Uiso 1 1 calc R . . C15 C 0.64702(18) -0.01210(7) 0.32151(15) 0.0288(5) Uani 1 1 d . . . H15A H 0.5818 -0.0050 0.2991 0.035 Uiso 1 1 calc R . . H15B H 0.6448 -0.0428 0.3455 0.035 Uiso 1 1 calc R . . O2 O 0.67290(11) 0.02026(5) 0.38195(10) 0.0247(3) Uani 1 1 d . . . C16 C 0.60760(16) 0.02008(7) 0.44846(14) 0.0262(5) Uani 1 1 d . . . H16A H 0.5979 -0.0113 0.4680 0.031 Uiso 1 1 calc R . . H16B H 0.5436 0.0323 0.4315 0.031 Uiso 1 1 calc R . . C17 C 0.64957(18) 0.04869(8) 0.51513(14) 0.0280(5) Uani 1 1 d . . . H17A H 0.6091 0.0459 0.5646 0.034 Uiso 1 1 calc R . . H17B H 0.7164 0.0384 0.5282 0.034 Uiso 1 1 calc R . . O3 O 0.65150(12) 0.09476(5) 0.48851(9) 0.0242(3) Uani 1 1 d . . . C18 C 0.68613(19) 0.12519(8) 0.54912(14) 0.0300(5) Uani 1 1 d . . . H18A H 0.6723 0.1123 0.6033 0.036 Uiso 1 1 calc R . . H18B H 0.6501 0.1541 0.5446 0.036 Uiso 1 1 calc R . . C19 C 0.79413(19) 0.13455(8) 0.54227(14) 0.0293(5) Uani 1 1 d . . . H19A H 0.8180 0.1497 0.5920 0.035 Uiso 1 1 calc R . . H19B H 0.8305 0.1059 0.5353 0.035 Uiso 1 1 calc R . . O4 O 0.80855(11) 0.16333(5) 0.47300(9) 0.0239(3) Uani 1 1 d . . . C20 C 0.89942(15) 0.18177(7) 0.46405(12) 0.0212(4) Uani 1 1 d . . . C21 C 0.97957(17) 0.17069(8) 0.51135(13) 0.0258(4) Uani 1 1 d . . . H21 H 0.9743 0.1475 0.5510 0.031 Uiso 1 1 calc R . . C22 C 1.06808(17) 0.19340(8) 0.50094(14) 0.0284(5) Uani 1 1 d . . . H22 H 1.1226 0.1859 0.5339 0.034 Uiso 1 1 calc R . . C23 C 1.07618(16) 0.22678(8) 0.44266(15) 0.0278(5) Uani 1 1 d . . . H23 H 1.1361 0.2424 0.4360 0.033 Uiso 1 1 calc R . . C24 C 0.99648(16) 0.23760(7) 0.39355(13) 0.0237(4) Uani 1 1 d . . . H24 H 1.0028 0.2603 0.3531 0.028 Uiso 1 1 calc R . . C25 C 0.90812(15) 0.21540(7) 0.40348(12) 0.0201(4) Uani 1 1 d . . . O5 O 0.82546(11) 0.22434(5) 0.35998(9) 0.0228(3) Uani 1 1 d . . . C26 C 0.83015(17) 0.26353(7) 0.30833(13) 0.0247(4) Uani 1 1 d . . . H26A H 0.8781 0.2584 0.2645 0.030 Uiso 1 1 calc R . . H26B H 0.8515 0.2901 0.3402 0.030 Uiso 1 1 calc R . . C27 C 0.73097(17) 0.27236(7) 0.27237(13) 0.0256(4) Uani 1 1 d . . . H27A H 0.6800 0.2675 0.3139 0.031 Uiso 1 1 calc R . . H27B H 0.7268 0.3041 0.2538 0.031 Uiso 1 1 calc R . . O6 O 0.71547(11) 0.24251(5) 0.20563(9) 0.0222(3) Uani 1 1 d . . . C28 C 0.62368(15) 0.25046(7) 0.16786(13) 0.0226(4) Uani 1 1 d . . . H28A H 0.6134 0.2834 0.1610 0.027 Uiso 1 1 calc R . . H28B H 0.5706 0.2385 0.2024 0.027 Uiso 1 1 calc R . . C29 C 0.62161(15) 0.22758(7) 0.08662(13) 0.0208(4) Uani 1 1 d . . . H29A H 0.5625 0.2370 0.0566 0.025 Uiso 1 1 calc R . . H29B H 0.6794 0.2368 0.0547 0.025 Uiso 1 1 calc R . . O7 O 0.62143(10) 0.17952(5) 0.09640(9) 0.0195(3) Uani 1 1 d . . . C30 C 0.63395(17) 0.15713(7) 0.02070(13) 0.0246(4) Uani 1 1 d . . . H30A H 0.7038 0.1573 0.0055 0.030 Uiso 1 1 calc R . . H30B H 0.5970 0.1733 -0.0219 0.030 Uiso 1 1 calc R . . C31 C 0.59817(17) 0.10889(8) 0.02660(14) 0.0259(4) Uani 1 1 d . . . H31A H 0.5266 0.1093 0.0344 0.031 Uiso 1 1 calc R . . H31B H 0.6114 0.0935 -0.0256 0.031 Uiso 1 1 calc R . . O8 O 0.64111(11) 0.08272(5) 0.09065(10) 0.0248(3) Uani 1 1 d . . . P1 P 0.0000 0.37482(3) 0.2500 0.0259(2) Uani 1 2 d S . . F1 F -0.0464(2) 0.41461(7) 0.19810(15) 0.0752(8) Uani 1 1 d . . . F2 F -0.0464(2) 0.33510(7) 0.19889(17) 0.0813(8) Uani 1 1 d . . . F3 F 0.0912(3) 0.37486(10) 0.1936(3) 0.1421(19) Uani 1 1 d . . . P2 P 0.51681(18) 0.39857(4) 0.2562(3) 0.0345(6) Uani 0.50 1 d P . . F4 F 0.4195(7) 0.3960(4) 0.3129(6) 0.071(2) Uani 0.50 1 d P . . F5 F 0.5415(4) 0.44757(17) 0.2903(4) 0.0702(17) Uani 0.50 1 d P . . F6 F 0.5758(4) 0.3771(2) 0.3297(3) 0.0851(17) Uani 0.50 1 d P . . F7 F 0.4946(7) 0.34969(16) 0.2234(3) 0.098(3) Uani 0.50 1 d P . . F8 F 0.4600(5) 0.4215(3) 0.1849(4) 0.108(3) Uani 0.50 1 d P . . F9 F 0.6128(7) 0.4016(3) 0.2075(5) 0.066(2) Uani 0.50 1 d P . . O9 O 0.2668(6) 0.3714(3) 0.1448(5) 0.053(3) Uani 0.288(9) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0172(9) 0.0187(9) 0.0217(9) 0.0029(7) -0.0012(7) 0.0008(7) C2 0.0177(9) 0.0192(9) 0.0190(9) 0.0032(7) 0.0017(7) -0.0013(7) C3 0.0135(9) 0.0160(8) 0.0177(8) -0.0022(7) 0.0017(7) -0.0004(6) C4 0.0168(9) 0.0238(9) 0.0178(9) 0.0039(7) -0.0005(7) 0.0004(7) C5 0.0182(9) 0.0235(10) 0.0181(9) 0.0026(7) 0.0023(7) -0.0023(7) N 0.0130(7) 0.0168(7) 0.0219(8) -0.0010(6) 0.0016(6) -0.0005(6) C6 0.0123(8) 0.0247(10) 0.0294(11) 0.0006(8) 0.0030(7) -0.0008(7) C7 0.0184(9) 0.0239(10) 0.0279(10) 0.0036(8) 0.0061(8) 0.0039(8) C8 0.0242(10) 0.0186(9) 0.0288(10) -0.0054(8) 0.0031(8) -0.0012(8) C9 0.0349(12) 0.0274(11) 0.0290(11) -0.0027(9) 0.0088(9) 0.0012(9) C10 0.0356(13) 0.0353(13) 0.0364(13) -0.0087(10) 0.0153(10) 0.0009(10) C11 0.0266(11) 0.0375(13) 0.0417(14) -0.0128(11) 0.0067(10) 0.0067(10) C12 0.0279(11) 0.0270(11) 0.0321(12) -0.0085(9) 0.0001(9) 0.0046(9) C13 0.0244(10) 0.0190(9) 0.0266(10) -0.0070(8) 0.0025(8) -0.0011(8) O1 0.0268(8) 0.0206(7) 0.0296(8) 0.0013(6) 0.0054(6) 0.0023(6) C14 0.0373(12) 0.0191(10) 0.0307(11) 0.0002(8) 0.0027(9) 0.0041(9) C15 0.0363(12) 0.0189(10) 0.0312(11) 0.0021(8) 0.0018(9) -0.0051(8) O2 0.0256(7) 0.0203(7) 0.0282(8) 0.0001(6) 0.0058(6) -0.0036(6) C16 0.0266(10) 0.0190(9) 0.0331(11) 0.0054(8) 0.0086(9) -0.0023(8) C17 0.0363(12) 0.0233(10) 0.0244(10) 0.0080(8) 0.0058(9) -0.0015(9) O3 0.0284(8) 0.0201(7) 0.0242(7) 0.0043(6) 0.0045(6) -0.0043(6) C18 0.0380(12) 0.0293(11) 0.0228(10) -0.0003(9) 0.0097(9) -0.0075(9) C19 0.0388(13) 0.0293(11) 0.0200(10) 0.0053(8) -0.0024(9) -0.0092(9) O4 0.0263(8) 0.0254(7) 0.0200(7) 0.0049(6) -0.0001(6) -0.0059(6) C20 0.0249(10) 0.0197(9) 0.0189(9) -0.0039(7) 0.0012(8) -0.0014(8) C21 0.0302(11) 0.0240(10) 0.0233(10) -0.0040(8) -0.0021(8) 0.0045(8) C22 0.0236(10) 0.0319(11) 0.0297(11) -0.0108(9) -0.0035(8) 0.0063(9) C23 0.0197(9) 0.0313(11) 0.0324(11) -0.0119(9) 0.0032(8) -0.0012(8) C24 0.0247(10) 0.0260(10) 0.0205(9) -0.0055(8) 0.0047(8) -0.0039(8) C25 0.0220(9) 0.0212(9) 0.0171(9) -0.0044(7) 0.0014(7) -0.0007(7) O5 0.0230(7) 0.0250(7) 0.0203(7) 0.0044(6) -0.0014(6) -0.0055(6) C26 0.0318(11) 0.0212(10) 0.0210(9) 0.0016(8) -0.0024(8) -0.0067(8) C27 0.0338(11) 0.0203(10) 0.0228(10) -0.0007(8) -0.0032(9) -0.0004(8) O6 0.0222(7) 0.0238(7) 0.0207(7) 0.0000(6) -0.0028(5) 0.0012(6) C28 0.0224(9) 0.0210(9) 0.0245(10) 0.0021(8) -0.0023(8) 0.0042(8) C29 0.0220(9) 0.0185(9) 0.0219(9) 0.0058(7) -0.0027(7) 0.0008(7) O7 0.0207(7) 0.0180(7) 0.0198(7) 0.0040(5) 0.0002(5) 0.0002(5) C30 0.0292(11) 0.0228(10) 0.0218(10) 0.0017(8) 0.0036(8) -0.0009(8) C31 0.0276(10) 0.0224(10) 0.0276(10) 0.0005(8) -0.0016(8) -0.0010(8) O8 0.0241(7) 0.0219(7) 0.0284(8) 0.0031(6) 0.0050(6) 0.0015(6) P1 0.0300(4) 0.0160(4) 0.0318(4) 0.000 -0.0069(3) 0.000 F1 0.1015(18) 0.0380(10) 0.0862(16) 0.0080(10) -0.0522(14) 0.0081(11) F2 0.108(2) 0.0404(11) 0.0953(18) -0.0213(11) -0.0323(16) -0.0123(12) F3 0.147(3) 0.0555(16) 0.223(5) 0.018(2) 0.118(3) 0.0056(17) P2 0.0430(19) 0.0337(6) 0.0267(13) 0.0001(7) 0.0113(14) -0.0028(6) F4 0.069(5) 0.075(4) 0.070(5) 0.035(3) 0.037(4) 0.019(3) F5 0.076(3) 0.048(3) 0.086(4) -0.025(2) 0.036(3) -0.014(2) F6 0.087(4) 0.107(4) 0.061(3) 0.037(3) 0.004(3) 0.019(3) F7 0.139(5) 0.050(2) 0.106(6) -0.032(3) 0.050(6) -0.039(4) F8 0.103(5) 0.147(7) 0.073(4) 0.060(5) -0.041(4) -0.010(5) F9 0.087(6) 0.053(3) 0.058(4) -0.014(3) 0.034(4) -0.013(4) O9 0.058(5) 0.062(5) 0.040(4) 0.013(3) 0.006(4) -0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N 1.345(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9500 . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 C3 1.482(4) 3_755 ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 N 1.346(3) . ? C5 H5 0.9500 . ? N C6 1.494(2) . ? C6 C7 1.513(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O8 1.372(3) . ? C8 C9 1.390(3) . ? C8 C13 1.412(3) . ? C9 C10 1.399(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.396(4) . ? C11 H11 0.9500 . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 O1 1.369(3) . ? O1 C14 1.440(3) . ? C14 C15 1.504(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O2 1.427(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O2 C16 1.417(3) . ? C16 C17 1.502(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O3 1.431(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O3 C18 1.427(3) . ? C18 C19 1.511(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O4 1.438(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? O4 C20 1.368(3) . ? C20 C21 1.387(3) . ? C20 C25 1.415(3) . ? C21 C22 1.398(3) . ? C21 H21 0.9500 . ? C22 C23 1.382(4) . ? C22 H22 0.9500 . ? C23 C24 1.398(3) . ? C23 H23 0.9500 . ? C24 C25 1.388(3) . ? C24 H24 0.9500 . ? C25 O5 1.368(3) . ? O5 C26 1.440(2) . ? C26 C27 1.507(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O6 1.427(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? O6 C28 1.424(2) . ? C28 C29 1.502(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O7 1.430(2) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? O7 C30 1.424(3) . ? C30 C31 1.511(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O8 1.436(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? P1 F3 1.559(3) 3 ? P1 F3 1.559(3) . ? P1 F2 1.579(2) . ? P1 F2 1.579(2) 3 ? P1 F1 1.588(2) 3 ? P1 F1 1.588(2) . ? P2 F9 1.545(10) . ? P2 F8 1.565(6) . ? P2 F7 1.573(5) . ? P2 F6 1.589(6) . ? P2 F5 1.590(5) . ? P2 F4 1.631(10) . ? 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 N C1 C2 120.42(18) . . ? N C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.40(18) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 119.04(17) . . ? C2 C3 C3 120.13(19) . 3_755 ? C4 C3 C3 120.8(2) . 3_755 ? C5 C4 C3 119.32(18) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N C5 C4 120.44(18) . . ? N C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C1 N C5 121.35(17) . . ? C1 N C6 119.41(17) . . ? C5 N C6 119.23(17) . . ? N C6 C7 110.21(17) . . ? N C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O8 C8 C9 125.0(2) . . ? O8 C8 C13 115.37(19) . . ? C9 C8 C13 119.6(2) . . ? C8 C9 C10 120.1(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.5(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? O1 C13 C12 123.9(2) . . ? O1 C13 C8 116.28(19) . . ? C12 C13 C8 119.8(2) . . ? C13 O1 C14 115.92(17) . . ? O1 C14 C15 108.32(18) . . ? O1 C14 H14A 110.0 . . ? C15 C14 H14A 110.0 . . ? O1 C14 H14B 110.0 . . ? C15 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? O2 C15 C14 108.30(18) . . ? O2 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? O2 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C16 O2 C15 112.44(17) . . ? O2 C16 C17 108.84(18) . . ? O2 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O2 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? O3 C17 C16 108.55(18) . . ? O3 C17 H17A 110.0 . . ? C16 C17 H17A 110.0 . . ? O3 C17 H17B 110.0 . . ? C16 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C18 O3 C17 113.03(17) . . ? O3 C18 C19 112.92(19) . . ? O3 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? O3 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? O4 C19 C18 107.61(19) . . ? O4 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? O4 C19 H19B 110.2 . . ? C18 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? C20 O4 C19 116.53(17) . . ? O4 C20 C21 124.53(19) . . ? O4 C20 C25 115.67(18) . . ? C21 C20 C25 119.8(2) . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 119.9(2) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 120.4(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? O5 C25 C24 124.78(19) . . ? O5 C25 C20 115.89(18) . . ? C24 C25 C20 119.3(2) . . ? C25 O5 C26 115.42(16) . . ? O5 C26 C27 109.41(17) . . ? O5 C26 H26A 109.8 . . ? C27 C26 H26A 109.8 . . ? O5 C26 H26B 109.8 . . ? C27 C26 H26B 109.8 . . ? H26A C26 H26B 108.2 . . ? O6 C27 C26 109.34(18) . . ? O6 C27 H27A 109.8 . . ? C26 C27 H27A 109.8 . . ? O6 C27 H27B 109.8 . . ? C26 C27 H27B 109.8 . . ? H27A C27 H27B 108.3 . . ? C28 O6 C27 111.54(16) . . ? O6 C28 C29 109.45(17) . . ? O6 C28 H28A 109.8 . . ? C29 C28 H28A 109.8 . . ? O6 C28 H28B 109.8 . . ? C29 C28 H28B 109.8 . . ? H28A C28 H28B 108.2 . . ? O7 C29 C28 110.29(16) . . ? O7 C29 H29A 109.6 . . ? C28 C29 H29A 109.6 . . ? O7 C29 H29B 109.6 . . ? C28 C29 H29B 109.6 . . ? H29A C29 H29B 108.1 . . ? C30 O7 C29 111.26(15) . . ? O7 C30 C31 110.05(17) . . ? O7 C30 H30A 109.6 . . ? C31 C30 H30A 109.6 . . ? O7 C30 H30B 109.6 . . ? C31 C30 H30B 109.6 . . ? H30A C30 H30B 108.2 . . ? O8 C31 C30 115.00(18) . . ? O8 C31 H31A 108.5 . . ? C30 C31 H31A 108.5 . . ? O8 C31 H31B 108.5 . . ? C30 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? C8 O8 C31 118.94(17) . . ? F3 P1 F3 179.9(2) 3 . ? F3 P1 F2 89.79(19) 3 . ? F3 P1 F2 90.3(2) . . ? F3 P1 F2 90.3(2) 3 3 ? F3 P1 F2 89.79(19) . 3 ? F2 P1 F2 83.95(19) . 3 ? F3 P1 F1 89.96(19) 3 3 ? F3 P1 F1 90.0(2) . 3 ? F2 P1 F1 179.65(16) . 3 ? F2 P1 F1 95.82(13) 3 3 ? F3 P1 F1 90.0(2) 3 . ? F3 P1 F1 89.96(19) . . ? F2 P1 F1 95.82(13) . . ? F2 P1 F1 179.65(16) 3 . ? F1 P1 F1 84.42(16) 3 . ? F9 P2 F8 90.5(5) . . ? F9 P2 F7 92.3(4) . . ? F8 P2 F7 92.4(5) . . ? F9 P2 F6 89.2(4) . . ? F8 P2 F6 177.8(5) . . ? F7 P2 F6 89.7(4) . . ? F9 P2 F5 87.1(4) . . ? F8 P2 F5 88.7(5) . . ? F7 P2 F5 178.7(5) . . ? F6 P2 F5 89.2(4) . . ? F9 P2 F4 176.3(6) . . ? F8 P2 F4 92.5(4) . . ? F7 P2 F4 89.8(5) . . ? F6 P2 F4 87.8(4) . . ? F5 P2 F4 90.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N C1 C2 C3 -2.3(3) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C1 C2 C3 C3 -177.93(16) . . . 3_755 ? C2 C3 C4 C5 0.8(3) . . . . ? C3 C3 C4 C5 179.65(16) 3_755 . . . ? C3 C4 C5 N -1.2(3) . . . . ? C2 C1 N C5 2.0(3) . . . . ? C2 C1 N C6 -179.36(18) . . . . ? C4 C5 N C1 -0.2(3) . . . . ? C4 C5 N C6 -178.85(19) . . . . ? C1 N C6 C7 -88.3(2) . . . . ? C5 N C6 C7 90.4(2) . . . . ? O8 C8 C9 C10 178.5(2) . . . . ? C13 C8 C9 C10 -1.7(3) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 O1 -179.9(2) . . . . ? C11 C12 C13 C8 0.2(3) . . . . ? O8 C8 C13 O1 1.0(3) . . . . ? C9 C8 C13 O1 -178.7(2) . . . . ? O8 C8 C13 C12 -178.99(19) . . . . ? C9 C8 C13 C12 1.2(3) . . . . ? C12 C13 O1 C14 -14.0(3) . . . . ? C8 C13 O1 C14 165.97(19) . . . . ? C13 O1 C14 C15 178.20(18) . . . . ? O1 C14 C15 O2 -80.6(2) . . . . ? C14 C15 O2 C16 -178.03(18) . . . . ? C15 O2 C16 C17 169.97(18) . . . . ? O2 C16 C17 O3 66.6(2) . . . . ? C16 C17 O3 C18 177.27(18) . . . . ? C17 O3 C18 C19 94.3(2) . . . . ? O3 C18 C19 O4 73.0(2) . . . . ? C18 C19 O4 C20 169.59(18) . . . . ? C19 O4 C20 C21 7.4(3) . . . . ? C19 O4 C20 C25 -170.37(18) . . . . ? O4 C20 C21 C22 -176.02(19) . . . . ? C25 C20 C21 C22 1.7(3) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 0.9(3) . . . . ? C23 C24 C25 O5 178.25(19) . . . . ? C23 C24 C25 C20 0.2(3) . . . . ? O4 C20 C25 O5 -1.8(3) . . . . ? C21 C20 C25 O5 -179.70(18) . . . . ? O4 C20 C25 C24 176.44(18) . . . . ? C21 C20 C25 C24 -1.5(3) . . . . ? C24 C25 O5 C26 -8.2(3) . . . . ? C20 C25 O5 C26 169.93(18) . . . . ? C25 O5 C26 C27 -173.19(17) . . . . ? O5 C26 C27 O6 -79.8(2) . . . . ? C26 C27 O6 C28 -178.21(17) . . . . ? C27 O6 C28 C29 165.17(17) . . . . ? O6 C28 C29 O7 68.3(2) . . . . ? C28 C29 O7 C30 -171.41(17) . . . . ? C29 O7 C30 C31 -159.70(17) . . . . ? O7 C30 C31 O8 -54.8(2) . . . . ? C9 C8 O8 C31 7.2(3) . . . . ? C13 C8 O8 C31 -172.59(18) . . . . ? C30 C31 O8 C8 -80.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.794 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.086 #===END data_mjm263 _database_code_depnum_ccdc_archive 'CCDC 721643' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4 (C16 H18 N2), 8 (C24 H32 O8), 8 (F6 P), 8 (C3 H6 O), C2 H3 N, H2 O' _chemical_formula_sum 'C282 H381 N9 O73 F48 P8' _chemical_formula_weight 6224.72 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.1988(10) _cell_length_b 32.459(2) _cell_length_c 16.0338(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.301(1) _cell_angle_gamma 90.00 _cell_volume 7329.6(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7659 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 21.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3272 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7647 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.043 before and 0.030 after correction. The Ratio of minimum to maximum transmission is 0.789538. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; The PLATON "squeeze" procedure was used to treat regions of diffuse solvent(s) which could not be modelled in terms of atomic sites. The number of electrons thus located, 152 per unit cell, is included in the formula, formula weight, calculated density, \m and F(000). This residual electron density was assigned to 4 molecules of acetone, 1 molecule of water and 1 molecule of acetonitrile per unit cell. This would give 154 e^-^. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22023 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 22.07 _reflns_number_total 4530 _reflns_number_gt 4113 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0322P)^2^+35.7526P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4530 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.2256(2) 0.14125(9) 0.18807(17) 0.0219(7) Uani 1 1 d . . . C1 C 0.1684(3) 0.10877(11) 0.1723(2) 0.0227(9) Uani 1 1 d . . . H1 H 0.1898 0.0855 0.1442 0.027 Uiso 1 1 calc R . . C2 C 0.0796(3) 0.10855(11) 0.1961(2) 0.0239(9) Uani 1 1 d . . . H2 H 0.0399 0.0851 0.1853 0.029 Uiso 1 1 calc R . . C3 C 0.0472(3) 0.14271(11) 0.2362(2) 0.0199(8) Uani 1 1 d . . . C4 C 0.1067(3) 0.17639(11) 0.2496(2) 0.0225(9) Uani 1 1 d . . . H4 H 0.0858 0.2005 0.2753 0.027 Uiso 1 1 calc R . . C5 C 0.1958(3) 0.17483(11) 0.2259(2) 0.0234(9) Uani 1 1 d . . . H5 H 0.2370 0.1978 0.2362 0.028 Uiso 1 1 calc R . . C6 C 0.3229(3) 0.14004(12) 0.1649(2) 0.0278(9) Uani 1 1 d . . . H6A H 0.3440 0.1110 0.1637 0.033 Uiso 1 1 calc R . . H6B H 0.3661 0.1546 0.2085 0.033 Uiso 1 1 calc R . . C7 C 0.3298(3) 0.15912(13) 0.0823(3) 0.0346(10) Uani 1 1 d . . . H7 H 0.2967 0.1840 0.0678 0.042 Uiso 1 1 calc R . . C8 C 0.3810(3) 0.14235(15) 0.0285(3) 0.0442(12) Uani 1 1 d . . . H8A H 0.4144 0.1174 0.0424 0.053 Uiso 1 1 calc R . . H8B H 0.3845 0.1551 -0.0243 0.053 Uiso 1 1 calc R . . O1 O 0.09681(18) 0.18323(8) 0.02060(16) 0.0306(7) Uani 1 1 d . . . C9 C 0.0394(3) 0.21240(12) 0.0496(2) 0.0282(10) Uani 1 1 d . . . C10 C -0.0589(3) 0.21159(13) 0.0375(2) 0.0332(10) Uani 1 1 d . . . H10 H -0.0911 0.1898 0.0062 0.040 Uiso 1 1 calc R . . C11 C -0.1108(3) 0.24240(14) 0.0707(2) 0.0364(11) Uani 1 1 d . . . H11 H -0.1782 0.2416 0.0620 0.044 Uiso 1 1 calc R . . C12 C -0.0655(3) 0.27383(14) 0.1159(3) 0.0389(11) Uani 1 1 d . . . H12 H -0.1012 0.2948 0.1390 0.047 Uiso 1 1 calc R . . C13 C 0.0331(3) 0.27505(13) 0.1280(3) 0.0349(10) Uani 1 1 d . . . H13 H 0.0645 0.2971 0.1589 0.042 Uiso 1 1 calc R . . C14 C 0.0861(3) 0.24480(12) 0.0959(2) 0.0298(10) Uani 1 1 d . . . O2 O 0.18344(18) 0.24358(8) 0.10491(16) 0.0316(7) Uani 1 1 d . . . C15 C 0.2327(3) 0.27612(12) 0.1531(3) 0.0355(10) Uani 1 1 d . . . H15A H 0.2122 0.2773 0.2098 0.043 Uiso 1 1 calc R . . H15B H 0.2179 0.3029 0.1250 0.043 Uiso 1 1 calc R . . C16 C 0.3370(3) 0.26803(12) 0.1602(3) 0.0349(10) Uani 1 1 d . . . H16A H 0.3539 0.2607 0.1041 0.042 Uiso 1 1 calc R . . H16B H 0.3716 0.2936 0.1787 0.042 Uiso 1 1 calc R . . O3 O 0.36723(18) 0.23579(8) 0.21789(15) 0.0278(6) Uani 1 1 d . . . C17 C 0.3902(3) 0.24929(12) 0.3034(2) 0.0314(10) Uani 1 1 d . . . H17A H 0.3333 0.2614 0.3237 0.038 Uiso 1 1 calc R . . H17B H 0.4402 0.2707 0.3067 0.038 Uiso 1 1 calc R . . C18 C 0.4241(3) 0.21348(12) 0.3568(2) 0.0309(10) Uani 1 1 d . . . H18A H 0.4737 0.1985 0.3308 0.037 Uiso 1 1 calc R . . H18B H 0.4524 0.2233 0.4129 0.037 Uiso 1 1 calc R . . O4 O 0.34720(18) 0.18649(8) 0.36562(15) 0.0302(7) Uani 1 1 d . . . C19 C 0.3748(3) 0.15335(13) 0.4221(2) 0.0371(11) Uani 1 1 d . . . H19A H 0.4051 0.1645 0.4765 0.044 Uiso 1 1 calc R . . H19B H 0.4217 0.1357 0.3984 0.044 Uiso 1 1 calc R . . C20 C 0.2902(3) 0.12840(13) 0.4360(2) 0.0353(10) Uani 1 1 d . . . H20A H 0.3026 0.1137 0.4904 0.042 Uiso 1 1 calc R . . H20B H 0.2349 0.1467 0.4382 0.042 Uiso 1 1 calc R . . O5 O 0.2699(2) 0.09929(8) 0.36911(15) 0.0328(7) Uani 1 1 d . . . C21 C 0.1988(3) 0.07156(12) 0.3773(2) 0.0312(10) Uani 1 1 d . . . C22 C 0.1374(3) 0.07390(13) 0.4375(2) 0.0351(11) Uani 1 1 d . . . H22 H 0.1442 0.0956 0.4777 0.042 Uiso 1 1 calc R . . C23 C 0.0659(3) 0.04481(14) 0.4398(3) 0.0392(11) Uani 1 1 d . . . H23 H 0.0246 0.0465 0.4819 0.047 Uiso 1 1 calc R . . C24 C 0.0548(3) 0.01373(14) 0.3816(3) 0.0422(12) Uani 1 1 d . . . H24 H 0.0046 -0.0056 0.3819 0.051 Uiso 1 1 calc R . . C25 C 0.1180(3) 0.01069(13) 0.3217(3) 0.0399(11) Uani 1 1 d . . . H25 H 0.1113 -0.0112 0.2820 0.048 Uiso 1 1 calc R . . C26 C 0.1889(3) 0.03875(13) 0.3196(2) 0.0343(10) Uani 1 1 d . . . O6 O 0.2544(2) 0.03818(8) 0.26334(17) 0.0373(7) Uani 1 1 d . . . C27 C 0.2511(4) 0.00323(13) 0.2067(3) 0.0468(12) Uani 1 1 d . . . H27A H 0.1870 0.0006 0.1747 0.056 Uiso 1 1 calc R . . H27B H 0.2658 -0.0225 0.2389 0.056 Uiso 1 1 calc R . . C28 C 0.3226(4) 0.01042(13) 0.1487(3) 0.0444(12) Uani 1 1 d . . . H28A H 0.3843 0.0168 0.1821 0.053 Uiso 1 1 calc R . . H28B H 0.3306 -0.0152 0.1169 0.053 Uiso 1 1 calc R . . O7 O 0.29798(19) 0.04295(8) 0.09105(16) 0.0323(7) Uani 1 1 d . . . C29 C 0.2363(3) 0.03110(13) 0.0185(3) 0.0413(11) Uani 1 1 d . . . H29A H 0.1756 0.0209 0.0351 0.050 Uiso 1 1 calc R . . H29B H 0.2655 0.0085 -0.0107 0.050 Uiso 1 1 calc R . . C30 C 0.2176(3) 0.06688(13) -0.0395(2) 0.0388(11) Uani 1 1 d . . . H30A H 0.2781 0.0811 -0.0455 0.047 Uiso 1 1 calc R . . H30B H 0.1898 0.0571 -0.0957 0.047 Uiso 1 1 calc R . . O8 O 0.1541(2) 0.09489(8) -0.00753(15) 0.0332(7) Uani 1 1 d . . . C31 C 0.1209(3) 0.12538(13) -0.0672(2) 0.0355(10) Uani 1 1 d . . . H31A H 0.0919 0.1119 -0.1197 0.043 Uiso 1 1 calc R . . H31B H 0.1751 0.1422 -0.0807 0.043 Uiso 1 1 calc R . . C32 C 0.0498(3) 0.15247(13) -0.0346(2) 0.0331(10) Uani 1 1 d . . . H32A H 0.0104 0.1661 -0.0821 0.040 Uiso 1 1 calc R . . H32B H 0.0074 0.1357 -0.0036 0.040 Uiso 1 1 calc R . . P P 0.70385(9) 0.37859(3) 0.18347(7) 0.0366(3) Uani 1 1 d . . . F1 F 0.78198(18) 0.40459(7) 0.14386(14) 0.0445(6) Uani 1 1 d . . . F2 F 0.6251(2) 0.35256(8) 0.22234(16) 0.0610(8) Uani 1 1 d . . . F3 F 0.6846(2) 0.35218(9) 0.09965(16) 0.0613(8) Uani 1 1 d . . . F4 F 0.7828(2) 0.34637(9) 0.21961(19) 0.0719(9) Uani 1 1 d . . . F5 F 0.7238(2) 0.40480(9) 0.26672(16) 0.0708(10) Uani 1 1 d . . . F6 F 0.6251(2) 0.41036(10) 0.1455(2) 0.0711(9) Uani 1 1 d . . . C33 C 0.0000 0.4199(3) 0.2500 0.124(5) Uani 1 2 d S . . O9 O 0.0000 0.4558(3) 0.2500 0.166(4) Uani 1 2 d S . . C34 C 0.0172(6) 0.3958(3) 0.1717(7) 0.151(4) Uani 1 1 d . . . H34A H 0.0147 0.4147 0.1237 0.226 Uiso 1 1 calc R . . H34B H -0.0319 0.3746 0.1599 0.226 Uiso 1 1 calc R . . H34C H 0.0798 0.3827 0.1810 0.226 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 N 0.0258(18) 0.0239(18) 0.0157(16) 0.0022(14) 0.0016(13) 0.0014(15) C1 0.034(2) 0.020(2) 0.0130(19) 0.0000(16) -0.0014(17) 0.0026(18) C2 0.031(2) 0.022(2) 0.018(2) 0.0021(16) 0.0029(17) -0.0048(17) C3 0.027(2) 0.020(2) 0.0122(18) 0.0033(15) 0.0002(15) 0.0031(17) C4 0.030(2) 0.020(2) 0.018(2) -0.0023(16) 0.0039(17) 0.0017(17) C5 0.030(2) 0.022(2) 0.018(2) 0.0037(16) -0.0015(17) -0.0026(17) C6 0.027(2) 0.030(2) 0.028(2) -0.0012(18) 0.0052(17) -0.0007(18) C7 0.032(2) 0.036(3) 0.035(2) 0.003(2) 0.004(2) -0.002(2) C8 0.036(3) 0.063(3) 0.034(3) -0.001(2) 0.006(2) -0.002(2) O1 0.0293(15) 0.0363(16) 0.0248(15) 0.0012(12) -0.0020(12) -0.0067(13) C9 0.031(2) 0.032(2) 0.021(2) 0.0129(18) 0.0022(18) -0.0003(19) C10 0.034(3) 0.041(3) 0.023(2) 0.0114(19) -0.0017(19) -0.010(2) C11 0.031(2) 0.049(3) 0.029(2) 0.015(2) 0.0039(19) 0.007(2) C12 0.042(3) 0.042(3) 0.033(2) 0.012(2) 0.006(2) 0.010(2) C13 0.037(3) 0.032(2) 0.035(2) 0.0044(19) 0.001(2) 0.001(2) C14 0.027(2) 0.033(2) 0.027(2) 0.0084(19) -0.0039(18) -0.0034(19) O2 0.0308(17) 0.0286(16) 0.0339(16) 0.0012(12) -0.0017(12) -0.0054(12) C15 0.038(3) 0.023(2) 0.042(3) 0.0052(19) -0.008(2) -0.0044(19) C16 0.037(3) 0.028(2) 0.038(3) 0.0068(19) 0.000(2) -0.0087(19) O3 0.0314(15) 0.0251(15) 0.0254(15) -0.0001(12) -0.0021(12) -0.0038(12) C17 0.033(2) 0.029(2) 0.032(2) -0.0066(19) 0.0033(19) -0.0033(18) C18 0.031(2) 0.036(2) 0.024(2) -0.0073(18) 0.0008(17) -0.0029(19) O4 0.0342(16) 0.0321(16) 0.0240(15) 0.0033(12) 0.0029(12) 0.0002(13) C19 0.044(3) 0.044(3) 0.022(2) 0.005(2) 0.0003(19) 0.004(2) C20 0.052(3) 0.040(3) 0.015(2) 0.0020(19) 0.0063(19) 0.005(2) O5 0.0450(17) 0.0339(16) 0.0212(15) 0.0015(12) 0.0111(12) 0.0021(14) C21 0.043(3) 0.031(2) 0.020(2) 0.0123(18) 0.0043(19) 0.009(2) C22 0.044(3) 0.039(3) 0.022(2) 0.0136(19) 0.007(2) 0.013(2) C23 0.043(3) 0.046(3) 0.030(2) 0.021(2) 0.009(2) 0.013(2) C24 0.040(3) 0.044(3) 0.042(3) 0.025(2) 0.001(2) 0.002(2) C25 0.054(3) 0.036(3) 0.028(2) 0.012(2) 0.000(2) -0.001(2) C26 0.048(3) 0.035(3) 0.022(2) 0.0126(19) 0.011(2) 0.007(2) O6 0.0588(19) 0.0269(16) 0.0288(16) 0.0029(12) 0.0159(14) 0.0035(14) C27 0.074(4) 0.024(2) 0.045(3) -0.002(2) 0.018(3) 0.004(2) C28 0.067(3) 0.028(2) 0.040(3) -0.003(2) 0.013(2) 0.014(2) O7 0.0423(17) 0.0300(16) 0.0246(15) -0.0055(12) 0.0039(13) 0.0034(13) C29 0.061(3) 0.034(3) 0.029(2) -0.007(2) 0.005(2) -0.005(2) C30 0.058(3) 0.037(3) 0.022(2) -0.0050(19) 0.005(2) -0.008(2) O8 0.0492(18) 0.0335(16) 0.0168(14) 0.0006(12) 0.0041(12) -0.0024(14) C31 0.043(3) 0.042(3) 0.020(2) 0.0043(19) -0.0013(19) -0.011(2) C32 0.032(2) 0.043(3) 0.023(2) 0.0046(19) -0.0047(18) -0.011(2) P 0.0569(8) 0.0314(6) 0.0217(6) -0.0023(5) 0.0057(5) -0.0126(6) F1 0.0549(16) 0.0482(15) 0.0302(13) 0.0008(11) 0.0043(11) -0.0167(12) F2 0.093(2) 0.0505(17) 0.0456(16) -0.0087(13) 0.0317(15) -0.0327(16) F3 0.078(2) 0.073(2) 0.0343(15) -0.0222(14) 0.0121(14) -0.0351(16) F4 0.087(2) 0.0531(18) 0.072(2) 0.0210(16) -0.0026(17) 0.0030(16) F5 0.126(3) 0.0600(19) 0.0302(15) -0.0166(13) 0.0258(16) -0.0412(18) F6 0.064(2) 0.072(2) 0.080(2) 0.0205(17) 0.0217(17) 0.0072(16) C33 0.067(7) 0.050(6) 0.234(16) 0.000 -0.066(8) 0.000 O9 0.165(8) 0.070(5) 0.234(11) 0.000 -0.091(8) 0.000 C34 0.082(6) 0.134(8) 0.229(11) -0.088(8) -0.005(6) 0.014(5) _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 N C1 1.335(5) . ? N C5 1.342(5) . ? N C6 1.476(5) . ? C1 C2 1.363(5) . ? C1 H1 0.9500 . ? C2 C3 1.388(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 C3 1.465(7) 2 ? C4 C5 1.367(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.477(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.314(6) . ? C7 H7 0.9500 . ? C8 H8A 0.9500 . ? C8 H8B 0.9500 . ? O1 C9 1.369(5) . ? O1 C32 1.441(5) . ? C9 C10 1.384(6) . ? C9 C14 1.404(6) . ? C10 C11 1.388(6) . ? C10 H10 0.9500 . ? C11 C12 1.364(6) . ? C11 H11 0.9500 . ? C12 C13 1.390(6) . ? C12 H12 0.9500 . ? C13 C14 1.376(6) . ? C13 H13 0.9500 . ? C14 O2 1.372(5) . ? O2 C15 1.437(5) . ? C15 C16 1.494(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O3 1.426(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O3 C17 1.436(4) . ? C17 C18 1.487(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O4 1.421(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O4 C19 1.429(5) . ? C19 C20 1.488(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O5 1.431(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? O5 C21 1.371(5) . ? C21 C22 1.382(6) . ? C21 C26 1.406(6) . ? C22 C23 1.391(6) . ? C22 H22 0.9500 . ? C23 C24 1.370(6) . ? C23 H23 0.9500 . ? C24 C25 1.398(6) . ? C24 H24 0.9500 . ? C25 C26 1.361(6) . ? C25 H25 0.9500 . ? C26 O6 1.376(5) . ? O6 C27 1.450(5) . ? C27 C28 1.479(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O7 1.418(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? O7 C29 1.418(5) . ? C29 C30 1.490(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O8 1.421(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? O8 C31 1.415(5) . ? C31 C32 1.484(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? P F5 1.578(3) . ? P F6 1.584(3) . ? P F4 1.588(3) . ? P F3 1.588(3) . ? P F1 1.589(3) . ? P F2 1.590(3) . ? C33 O9 1.165(11) . ? C33 C34 1.525(9) 2 ? C33 C34 1.525(9) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 N C5 120.5(3) . . ? C1 N C6 119.9(3) . . ? C5 N C6 119.6(3) . . ? N C1 C2 120.9(3) . . ? N C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.8(3) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 118.2(3) . . ? C4 C3 C3 121.2(2) . 2 ? C2 C3 C3 120.6(2) . 2 ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N C5 C4 120.8(3) . . ? N C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? N C6 C7 112.7(3) . . ? N C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 121.4(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 H8A 120.0 . . ? C7 C8 H8B 120.0 . . ? H8A C8 H8B 120.0 . . ? C9 O1 C32 116.0(3) . . ? O1 C9 C10 125.0(4) . . ? O1 C9 C14 115.8(3) . . ? C10 C9 C14 119.2(4) . . ? C9 C10 C11 120.5(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.6(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? O2 C14 C13 124.9(4) . . ? O2 C14 C9 115.9(4) . . ? C13 C14 C9 119.2(4) . . ? C14 O2 C15 116.8(3) . . ? O2 C15 C16 108.8(3) . . ? O2 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? O2 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? O3 C16 C15 113.1(3) . . ? O3 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? O3 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 O3 C17 114.1(3) . . ? O3 C17 C18 109.2(3) . . ? O3 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? O3 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? O4 C18 C17 110.1(3) . . ? O4 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? O4 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.2 . . ? C18 O4 C19 112.0(3) . . ? O4 C19 C20 110.0(3) . . ? O4 C19 H19A 109.7 . . ? C20 C19 H19A 109.7 . . ? O4 C19 H19B 109.7 . . ? C20 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? O5 C20 C19 109.7(3) . . ? O5 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? O5 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C21 O5 C20 116.3(3) . . ? O5 C21 C22 124.6(4) . . ? O5 C21 C26 116.6(3) . . ? C22 C21 C26 118.8(4) . . ? C21 C22 C23 120.6(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 120.2(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.5(4) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 120.7(4) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 O6 124.8(4) . . ? C25 C26 C21 120.2(4) . . ? O6 C26 C21 115.0(4) . . ? C26 O6 C27 116.8(3) . . ? O6 C27 C28 107.5(4) . . ? O6 C27 H27A 110.2 . . ? C28 C27 H27A 110.2 . . ? O6 C27 H27B 110.2 . . ? C28 C27 H27B 110.2 . . ? H27A C27 H27B 108.5 . . ? O7 C28 C27 113.3(4) . . ? O7 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? O7 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 O7 C29 114.1(3) . . ? O7 C29 C30 110.0(3) . . ? O7 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? O7 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? O8 C30 C29 110.2(3) . . ? O8 C30 H30A 109.6 . . ? C29 C30 H30A 109.6 . . ? O8 C30 H30B 109.6 . . ? C29 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? C31 O8 C30 112.0(3) . . ? O8 C31 C32 111.0(3) . . ? O8 C31 H31A 109.4 . . ? C32 C31 H31A 109.4 . . ? O8 C31 H31B 109.4 . . ? C32 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? O1 C32 C31 110.1(3) . . ? O1 C32 H32A 109.6 . . ? C31 C32 H32A 109.6 . . ? O1 C32 H32B 109.6 . . ? C31 C32 H32B 109.6 . . ? H32A C32 H32B 108.2 . . ? F5 P F6 90.91(19) . . ? F5 P F4 90.23(18) . . ? F6 P F4 178.82(19) . . ? F5 P F3 179.6(2) . . ? F6 P F3 89.38(18) . . ? F4 P F3 89.48(17) . . ? F5 P F1 89.57(14) . . ? F6 P F1 89.74(15) . . ? F4 P F1 89.97(16) . . ? F3 P F1 90.15(14) . . ? F5 P F2 90.82(15) . . ? F6 P F2 89.96(17) . . ? F4 P F2 90.32(17) . . ? F3 P F2 89.46(14) . . ? F1 P F2 179.51(16) . . ? O9 C33 C34 120.8(5) . 2 ? O9 C33 C34 120.8(5) . . ? C34 C33 C34 118.4(11) 2 . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N C1 C2 -1.7(5) . . . . ? C6 N C1 C2 177.4(3) . . . . ? N C1 C2 C3 0.9(5) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C1 C2 C3 C3 -178.7(4) . . . 2 ? C2 C3 C4 C5 -2.0(5) . . . . ? C3 C3 C4 C5 177.6(4) 2 . . . ? C1 N C5 C4 0.6(5) . . . . ? C6 N C5 C4 -178.5(3) . . . . ? C3 C4 C5 N 1.3(5) . . . . ? C1 N C6 C7 95.6(4) . . . . ? C5 N C6 C7 -85.3(4) . . . . ? N C6 C7 C8 -138.3(4) . . . . ? C32 O1 C9 C10 7.6(5) . . . . ? C32 O1 C9 C14 -173.4(3) . . . . ? O1 C9 C10 C11 178.9(3) . . . . ? C14 C9 C10 C11 0.0(5) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C10 C11 C12 C13 0.5(6) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C12 C13 C14 O2 -179.9(4) . . . . ? C12 C13 C14 C9 0.6(6) . . . . ? O1 C9 C14 O2 1.2(5) . . . . ? C10 C9 C14 O2 -179.8(3) . . . . ? O1 C9 C14 C13 -179.2(3) . . . . ? C10 C9 C14 C13 -0.2(5) . . . . ? C13 C14 O2 C15 1.3(5) . . . . ? C9 C14 O2 C15 -179.1(3) . . . . ? C14 O2 C15 C16 176.5(3) . . . . ? O2 C15 C16 O3 -74.6(4) . . . . ? C15 C16 O3 C17 -87.4(4) . . . . ? C16 O3 C17 C18 -177.9(3) . . . . ? O3 C17 C18 O4 -71.0(4) . . . . ? C17 C18 O4 C19 -175.2(3) . . . . ? C18 O4 C19 C20 174.3(3) . . . . ? O4 C19 C20 O5 83.0(4) . . . . ? C19 C20 O5 C21 174.3(3) . . . . ? C20 O5 C21 C22 10.4(5) . . . . ? C20 O5 C21 C26 -169.7(3) . . . . ? O5 C21 C22 C23 178.5(3) . . . . ? C26 C21 C22 C23 -1.4(6) . . . . ? C21 C22 C23 C24 -0.8(6) . . . . ? C22 C23 C24 C25 2.2(6) . . . . ? C23 C24 C25 C26 -1.4(6) . . . . ? C24 C25 C26 O6 179.8(4) . . . . ? C24 C25 C26 C21 -0.7(6) . . . . ? O5 C21 C26 C25 -177.7(3) . . . . ? C22 C21 C26 C25 2.1(6) . . . . ? O5 C21 C26 O6 1.8(5) . . . . ? C22 C21 C26 O6 -178.3(3) . . . . ? C25 C26 O6 C27 -4.9(6) . . . . ? C21 C26 O6 C27 175.6(3) . . . . ? C26 O6 C27 C28 176.2(3) . . . . ? O6 C27 C28 O7 -69.5(5) . . . . ? C27 C28 O7 C29 -83.8(4) . . . . ? C28 O7 C29 C30 -177.9(3) . . . . ? O7 C29 C30 O8 -74.7(4) . . . . ? C29 C30 O8 C31 -169.3(3) . . . . ? C30 O8 C31 C32 176.1(3) . . . . ? C9 O1 C32 C31 174.7(3) . . . . ? O8 C31 C32 O1 80.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.07 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.450 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.056 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.756 284 76 '2 (C3 H6 O), 0.5 (C2 H3 N), 0.5 (H2 O)' 2 0.500 0.000 0.884 284 76 '2 (C3 H6 O), 0.5 (C2 H3 N), 0.5 (H2 O)' _platon_squeeze_details ; ; #===END data_mjm281 _database_code_depnum_ccdc_archive 'CCDC 721644' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2, 2 (C24 H32 O8), 2 (F6 P), 0.6 (H2 O)' _chemical_formula_sum 'C60 H79.2 N2 O16.6 F12 P2' _chemical_formula_weight 1382.44 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' _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 16.3602(17) _cell_length_b 13.2368(14) _cell_length_c 29.792(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.006(2) _cell_angle_gamma 90.00 _cell_volume 6451.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6811 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 24.38 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2893 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8076 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.104 before and 0.037 after correction. The Ratio of minimum to maximum transmission is 0.821434. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; Protons of the water molecule could not be detected. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50203 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 0.68 _diffrn_reflns_theta_max 24.81 _reflns_number_total 11061 _reflns_number_gt 10356 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1181P)^2^+6.4343P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11061 _refine_ls_number_parameters 867 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1794 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3341(2) 0.3182(3) 0.10219(12) 0.0241(7) Uani 1 1 d . . . H1 H 0.3802 0.2884 0.0880 0.029 Uiso 1 1 calc R . . C2 C 0.3237(2) 0.4209(3) 0.10080(12) 0.0243(7) Uani 1 1 d . . . H2 H 0.3633 0.4624 0.0865 0.029 Uiso 1 1 calc R . . C3 C 0.2552(2) 0.4638(3) 0.12027(11) 0.0212(7) Uani 1 1 d . . . C4 C 0.1989(2) 0.4006(3) 0.14118(12) 0.0235(7) Uani 1 1 d . . . H4 H 0.1509 0.4282 0.1542 0.028 Uiso 1 1 calc R . . C5 C 0.2127(2) 0.2989(3) 0.14295(12) 0.0255(8) Uani 1 1 d . . . H5 H 0.1750 0.2561 0.1579 0.031 Uiso 1 1 calc R . . N1 N 0.27959(19) 0.2592(2) 0.12355(10) 0.0231(6) Uani 1 1 d . . . C6 C 0.2938(3) 0.1495(3) 0.12560(14) 0.0318(9) Uani 1 1 d . . . H6A H 0.2975 0.1223 0.0951 0.048 Uiso 1 1 calc R . . H6B H 0.2483 0.1170 0.1414 0.048 Uiso 1 1 calc R . . H6C H 0.3449 0.1361 0.1417 0.048 Uiso 1 1 calc R . . C7 C 0.2907(2) 0.7369(3) 0.14467(12) 0.0251(7) Uani 1 1 d . . . H7 H 0.3309 0.7781 0.1586 0.030 Uiso 1 1 calc R . . C8 C 0.3040(2) 0.6355(3) 0.13991(12) 0.0234(7) Uani 1 1 d . . . H8 H 0.3547 0.6071 0.1489 0.028 Uiso 1 1 calc R . . C9 C 0.2436(2) 0.5741(3) 0.12193(11) 0.0212(7) Uani 1 1 d . . . C10 C 0.1717(2) 0.6195(3) 0.10742(12) 0.0252(7) Uani 1 1 d . . . H10 H 0.1293 0.5794 0.0949 0.030 Uiso 1 1 calc R . . C11 C 0.1620(2) 0.7214(3) 0.11104(12) 0.0252(8) Uani 1 1 d . . . H11 H 0.1134 0.7524 0.1003 0.030 Uiso 1 1 calc R . . N2 N 0.22091(19) 0.7782(2) 0.12978(10) 0.0246(6) Uani 1 1 d . . . C12 C 0.2083(3) 0.8880(3) 0.13476(14) 0.0360(9) Uani 1 1 d . . . H12A H 0.1747 0.9128 0.1099 0.054 Uiso 1 1 calc R . . H12B H 0.2614 0.9224 0.1344 0.054 Uiso 1 1 calc R . . H12C H 0.1806 0.9016 0.1633 0.054 Uiso 1 1 calc R . . O1 O 0.20982(18) 0.2173(2) 0.02888(9) 0.0351(6) Uani 1 1 d . . . C13 C 0.2645(3) 0.2432(3) -0.00743(12) 0.0350(9) Uani 1 1 d . . . H13A H 0.2900 0.3098 -0.0017 0.042 Uiso 1 1 calc R . . H13B H 0.2337 0.2473 -0.0360 0.042 Uiso 1 1 calc R . . C14 C 0.3282(2) 0.1642(3) -0.01056(12) 0.0329(9) Uani 1 1 d . . . H14A H 0.3032 0.0966 -0.0069 0.040 Uiso 1 1 calc R . . H14B H 0.3549 0.1670 -0.0403 0.040 Uiso 1 1 calc R . . O2 O 0.38680(17) 0.1811(2) 0.02377(9) 0.0303(6) Uani 1 1 d . . . C15 C 0.4510(3) 0.1081(3) 0.02370(13) 0.0340(9) Uani 1 1 d . . . H15A H 0.4688 0.0944 -0.0075 0.041 Uiso 1 1 calc R . . H15B H 0.4315 0.0440 0.0370 0.041 Uiso 1 1 calc R . . C16 C 0.5210(3) 0.1486(3) 0.05043(14) 0.0352(9) Uani 1 1 d . . . H16A H 0.5685 0.1026 0.0479 0.042 Uiso 1 1 calc R . . H16B H 0.5372 0.2157 0.0387 0.042 Uiso 1 1 calc R . . O3 O 0.49691(15) 0.1572(2) 0.09644(9) 0.0309(6) Uani 1 1 d . . . C17 C 0.5594(2) 0.2003(3) 0.12408(16) 0.0388(10) Uani 1 1 d . . . H17A H 0.6131 0.1899 0.1095 0.047 Uiso 1 1 calc R . . H17B H 0.5603 0.1646 0.1533 0.047 Uiso 1 1 calc R . . C18 C 0.5473(2) 0.3103(3) 0.13226(14) 0.0354(9) Uani 1 1 d . . . H18A H 0.5965 0.3396 0.1466 0.042 Uiso 1 1 calc R . . H18B H 0.5377 0.3459 0.1035 0.042 Uiso 1 1 calc R . . O4 O 0.47790(16) 0.3214(2) 0.16120(9) 0.0312(6) Uani 1 1 d . . . C19 C 0.4661(2) 0.4145(3) 0.18068(12) 0.0248(7) Uani 1 1 d . . . C20 C 0.5092(2) 0.5003(3) 0.17105(14) 0.0334(9) Uani 1 1 d . . . H20 H 0.5488 0.4993 0.1478 0.040 Uiso 1 1 calc R . . C21 C 0.4958(2) 0.5884(3) 0.19471(15) 0.0348(9) Uani 1 1 d . . . H21 H 0.5264 0.6474 0.1878 0.042 Uiso 1 1 calc R . . C22 C 0.4380(2) 0.5908(3) 0.22834(14) 0.0338(9) Uani 1 1 d . . . H22 H 0.4292 0.6513 0.2448 0.041 Uiso 1 1 calc R . . C23 C 0.3917(2) 0.5036(3) 0.23840(14) 0.0299(8) Uani 1 1 d . . . H23 H 0.3510 0.5056 0.2611 0.036 Uiso 1 1 calc R . . C24 C 0.4061(2) 0.4152(3) 0.21487(13) 0.0263(8) Uani 1 1 d . . . O5 O 0.36536(16) 0.32607(19) 0.22139(9) 0.0291(6) Uani 1 1 d . . . C25 C 0.3177(3) 0.3189(3) 0.26148(14) 0.0342(9) Uani 1 1 d . . . H25A H 0.2708 0.3660 0.2598 0.041 Uiso 1 1 calc R . . H25B H 0.3515 0.3378 0.2877 0.041 Uiso 1 1 calc R . . C26 C 0.2872(3) 0.2128(3) 0.26685(15) 0.0370(9) Uani 1 1 d . . . H26A H 0.3317 0.1644 0.2602 0.044 Uiso 1 1 calc R . . H26B H 0.2691 0.2016 0.2982 0.044 Uiso 1 1 calc R . . O6 O 0.22068(16) 0.1970(2) 0.23682(9) 0.0315(6) Uani 1 1 d . . . C27 C 0.1818(3) 0.1033(3) 0.24389(14) 0.0333(9) Uani 1 1 d . . . H27A H 0.1753 0.0911 0.2765 0.040 Uiso 1 1 calc R . . H27B H 0.2158 0.0482 0.2313 0.040 Uiso 1 1 calc R . . C28 C 0.0998(2) 0.1036(3) 0.22168(14) 0.0336(9) Uani 1 1 d . . . H28A H 0.0682 0.0439 0.2316 0.040 Uiso 1 1 calc R . . H28B H 0.0693 0.1649 0.2308 0.040 Uiso 1 1 calc R . . O7 O 0.10816(17) 0.1019(2) 0.17479(10) 0.0356(7) Uani 1 1 d . . . C29 C 0.0293(3) 0.1243(4) 0.15506(16) 0.0450(11) Uani 1 1 d . . . H29A H 0.0158 0.1965 0.1593 0.054 Uiso 1 1 calc R . . H29B H -0.0137 0.0831 0.1696 0.054 Uiso 1 1 calc R . . C30 C 0.0339(3) 0.1000(4) 0.10611(17) 0.0518(12) Uani 1 1 d . . . H30A H 0.0418 0.0262 0.1027 0.062 Uiso 1 1 calc R . . H30B H -0.0190 0.1174 0.0920 0.062 Uiso 1 1 calc R . . O8 O 0.0981(2) 0.1511(3) 0.08213(11) 0.0476(8) Uani 1 1 d . . . C31 C 0.0868(3) 0.2478(4) 0.06636(14) 0.0417(10) Uani 1 1 d . . . C32 C 0.0207(3) 0.3084(4) 0.07612(16) 0.0507(12) Uani 1 1 d . . . H32 H -0.0219 0.2839 0.0949 0.061 Uiso 1 1 calc R . . C33 C 0.0164(3) 0.4053(5) 0.05841(17) 0.0569(15) Uani 1 1 d . . . H33 H -0.0285 0.4476 0.0659 0.068 Uiso 1 1 calc R . . C34 C 0.0763(3) 0.4406(4) 0.03024(18) 0.0542(14) Uani 1 1 d . . . H34 H 0.0725 0.5069 0.0183 0.065 Uiso 1 1 calc R . . C35 C 0.1420(3) 0.3801(4) 0.01919(15) 0.0428(11) Uani 1 1 d . . . H35 H 0.1831 0.4045 -0.0006 0.051 Uiso 1 1 calc R . . C36 C 0.1479(3) 0.2839(3) 0.03703(13) 0.0356(9) Uani 1 1 d . . . O9 O 0.13519(16) 0.6976(2) 0.22515(9) 0.0307(6) Uani 1 1 d . . . C37 C 0.1873(3) 0.7126(4) 0.26303(15) 0.0454(11) Uani 1 1 d . . . H37A H 0.2380 0.6724 0.2595 0.054 Uiso 1 1 calc R . . H37B H 0.1594 0.6900 0.2907 0.054 Uiso 1 1 calc R . . C38 C 0.2076(4) 0.8205(5) 0.26639(19) 0.075(2) Uani 1 1 d . . . H38A H 0.1576 0.8608 0.2608 0.091 Uiso 1 1 calc R . . H38B H 0.2263 0.8354 0.2973 0.091 Uiso 1 1 calc R . . O10 O 0.2697(2) 0.8509(3) 0.23524(11) 0.0592(11) Uani 1 1 d . . . C39 C 0.3415(3) 0.8885(3) 0.25432(13) 0.0315(8) Uani 1 1 d . . . H39A H 0.3737 0.8317 0.2667 0.038 Uiso 1 1 calc R . . H39B H 0.3273 0.9342 0.2794 0.038 Uiso 1 1 calc R . . C40 C 0.3920(3) 0.9441(4) 0.22140(15) 0.0454(11) Uani 1 1 d . . . H40A H 0.3609 1.0039 0.2111 0.055 Uiso 1 1 calc R . . H40B H 0.4418 0.9689 0.2368 0.055 Uiso 1 1 calc R . . O11 O 0.4151(2) 0.8893(2) 0.18469(11) 0.0459(8) Uani 1 1 d . . . C41 C 0.4649(3) 0.9416(4) 0.15391(14) 0.0456(11) Uani 1 1 d . . . H41A H 0.5150 0.9661 0.1690 0.055 Uiso 1 1 calc R . . H41B H 0.4352 1.0005 0.1416 0.055 Uiso 1 1 calc R . . C42 C 0.4862(3) 0.8715(4) 0.11783(15) 0.0452(11) Uani 1 1 d . . . H42A H 0.5323 0.8988 0.1000 0.054 Uiso 1 1 calc R . . H42B H 0.5030 0.8056 0.1306 0.054 Uiso 1 1 calc R . . O12 O 0.41541(19) 0.8588(2) 0.08967(10) 0.0405(7) Uani 1 1 d . . . C43 C 0.4161(3) 0.7734(4) 0.06380(14) 0.0417(10) Uani 1 1 d . . . C44 C 0.4749(4) 0.7005(4) 0.06264(19) 0.0608(14) Uani 1 1 d . . . H44 H 0.5231 0.7078 0.0801 0.073 Uiso 1 1 calc R . . C45 C 0.4642(5) 0.6138(5) 0.0353(2) 0.0728(18) Uani 1 1 d . . . H45 H 0.5041 0.5617 0.0347 0.087 Uiso 1 1 calc R . . C46 C 0.3953(4) 0.6074(5) 0.0101(2) 0.0675(16) Uani 1 1 d . . . H46 H 0.3883 0.5498 -0.0085 0.081 Uiso 1 1 calc R . . C47 C 0.3361(4) 0.6788(4) 0.01002(18) 0.0564(13) Uani 1 1 d . . . H47 H 0.2891 0.6704 -0.0084 0.068 Uiso 1 1 calc R . . C48 C 0.3434(3) 0.7629(4) 0.03627(14) 0.0499(13) Uani 1 1 d . . . O13 O 0.2867(2) 0.8380(3) 0.03823(11) 0.0502(9) Uani 1 1 d . . . C49 C 0.2251(4) 0.8431(5) 0.00250(15) 0.0579(14) Uani 1 1 d . . . H49A H 0.1927 0.7800 0.0021 0.070 Uiso 1 1 calc R . . H49B H 0.2524 0.8503 -0.0270 0.070 Uiso 1 1 calc R . . C50 C 0.1705(3) 0.9304(4) 0.01035(17) 0.0562(14) Uani 1 1 d . . . H50A H 0.2030 0.9864 0.0233 0.067 Uiso 1 1 calc R . . H50B H 0.1486 0.9536 -0.0188 0.067 Uiso 1 1 calc R . . O14 O 0.1032(2) 0.9082(3) 0.03996(11) 0.0482(8) Uani 1 1 d . . . C51 C 0.0378(3) 0.8662(4) 0.01754(15) 0.0465(11) Uani 1 1 d . . . H51A H 0.0548 0.8017 0.0035 0.056 Uiso 1 1 calc R . . H51B H 0.0196 0.9125 -0.0066 0.056 Uiso 1 1 calc R . . C52 C -0.0303(3) 0.8475(3) 0.04882(16) 0.0392(10) Uani 1 1 d . . . H52A H -0.0451 0.9117 0.0638 0.047 Uiso 1 1 calc R . . H52B H -0.0785 0.8241 0.0316 0.047 Uiso 1 1 calc R . . O15 O -0.01096(19) 0.7754(3) 0.08151(11) 0.0531(9) Uani 1 1 d . . . C53 C -0.0696(3) 0.7611(4) 0.11454(15) 0.0402(10) Uani 1 1 d . . . H53A H -0.1245 0.7595 0.1006 0.048 Uiso 1 1 calc R . . H53B H -0.0680 0.8184 0.1359 0.048 Uiso 1 1 calc R . . C54 C -0.0555(3) 0.6653(4) 0.13932(16) 0.0433(11) Uani 1 1 d . . . H54A H -0.1039 0.6492 0.1580 0.052 Uiso 1 1 calc R . . H54B H -0.0471 0.6093 0.1178 0.052 Uiso 1 1 calc R . . O16 O 0.01569(17) 0.6757(2) 0.16760(10) 0.0365(7) Uani 1 1 d . . . C55 C 0.0366(2) 0.5929(3) 0.19060(13) 0.0286(8) Uani 1 1 d . . . C56 C -0.0003(2) 0.4956(3) 0.18664(14) 0.0340(9) Uani 1 1 d . . . H56 H -0.0431 0.4847 0.1656 0.041 Uiso 1 1 calc R . . C57 C 0.0266(3) 0.4176(3) 0.21356(16) 0.0408(11) Uani 1 1 d . . . H57 H 0.0015 0.3532 0.2106 0.049 Uiso 1 1 calc R . . C58 C 0.0869(3) 0.4287(3) 0.24378(16) 0.0402(10) Uani 1 1 d . . . H58 H 0.1033 0.3740 0.2623 0.048 Uiso 1 1 calc R . . C59 C 0.1242(3) 0.5217(3) 0.24719(15) 0.0371(10) Uani 1 1 d . . . H59 H 0.1677 0.5293 0.2680 0.044 Uiso 1 1 calc R . . C60 C 0.1012(2) 0.6043(3) 0.22179(13) 0.0272(8) Uani 1 1 d . . . P1 P 0.24678(7) 0.48809(8) 0.37425(3) 0.0294(2) Uani 1 1 d . . . F1 F 0.2116(2) 0.4272(3) 0.41539(10) 0.0716(11) Uani 1 1 d . A . F2 F 0.2821(2) 0.5484(3) 0.33303(11) 0.0719(10) Uani 1 1 d . A . F3 F 0.2079(5) 0.4104(6) 0.3372(2) 0.0275(18) Uiso 0.384(10) 1 d P A 1 F4 F 0.1659(6) 0.5483(8) 0.3786(3) 0.058(3) Uiso 0.384(10) 1 d P A 1 F5 F 0.2916(5) 0.5542(6) 0.4115(2) 0.034(2) Uiso 0.384(10) 1 d P A 1 F6 F 0.3320(6) 0.4272(8) 0.3682(3) 0.055(3) Uiso 0.384(10) 1 d P A 1 F13 F 0.2415(7) 0.3818(7) 0.3508(3) 0.049(3) Uiso 0.304(6) 1 d P A 2 F14 F 0.1511(6) 0.5089(7) 0.3593(3) 0.044(3) Uiso 0.304(6) 1 d P A 2 F15 F 0.2523(6) 0.5965(6) 0.3989(3) 0.040(2) Uiso 0.304(6) 1 d P A 2 F16 F 0.3354(6) 0.4684(8) 0.3874(4) 0.045(3) Uiso 0.304(6) 1 d P A 2 F23 F 0.1874(7) 0.4455(10) 0.3398(3) 0.047(3) Uiso 0.313(9) 1 d P A 3 F24 F 0.2036(10) 0.5923(10) 0.3814(4) 0.076(4) Uiso 0.313(9) 1 d P A 3 F25 F 0.3190(6) 0.5223(7) 0.4110(3) 0.034(2) Uiso 0.313(9) 1 d P A 3 F26 F 0.3053(7) 0.3884(9) 0.3719(4) 0.056(3) Uiso 0.313(9) 1 d P A 3 F7 F 0.1589(2) 0.9469(3) 0.37765(14) 0.0861(12) Uani 1 1 d . . . P2 P 0.24491(10) 0.98120(16) 0.39800(4) 0.0692(5) Uani 1 1 d . . . F8 F 0.3316(3) 1.0124(4) 0.41754(17) 0.1119(18) Uani 1 1 d . . . F9 F 0.2766(2) 0.8683(3) 0.39394(14) 0.0852(12) Uani 1 1 d . . . F10 F 0.2761(3) 1.0038(3) 0.34929(11) 0.0759(11) Uani 1 1 d . . . F11 F 0.2139(3) 1.0944(4) 0.40303(14) 0.0985(15) Uani 1 1 d . . . F12 F 0.2121(3) 0.9525(5) 0.44693(13) 0.129(2) Uani 1 1 d . . . O21 O 0.6422(7) 0.7190(8) 0.1258(4) 0.054(4) Uani 0.338(12) 1 d P . . O22 O 0.8577(11) 0.2546(15) 0.1287(8) 0.093(8) Uani 0.260(14) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0215(17) 0.0309(19) 0.0199(17) -0.0028(14) 0.0035(14) -0.0020(15) C2 0.0225(17) 0.0263(18) 0.0240(18) -0.0029(14) 0.0041(15) -0.0046(14) C3 0.0207(17) 0.0239(16) 0.0191(16) -0.0011(13) -0.0058(14) 0.0007(14) C4 0.0239(18) 0.0229(17) 0.0238(18) 0.0025(14) 0.0060(14) 0.0027(14) C5 0.0249(17) 0.0295(18) 0.0221(17) 0.0045(14) 0.0061(15) 0.0042(15) N1 0.0243(14) 0.0240(14) 0.0210(14) -0.0014(12) 0.0015(12) 0.0026(12) C6 0.037(2) 0.0255(19) 0.032(2) 0.0028(16) 0.0076(18) 0.0068(16) C7 0.0288(18) 0.0276(18) 0.0190(17) 0.0020(14) -0.0021(14) -0.0055(15) C8 0.0193(16) 0.0296(18) 0.0212(18) 0.0013(14) -0.0022(14) 0.0007(14) C9 0.0220(17) 0.0258(17) 0.0158(15) 0.0032(13) 0.0021(14) 0.0015(14) C10 0.0205(17) 0.0285(18) 0.0267(19) 0.0031(15) -0.0035(15) -0.0036(14) C11 0.0248(18) 0.0273(18) 0.0234(18) 0.0078(14) -0.0036(14) 0.0021(15) N2 0.0297(16) 0.0240(15) 0.0202(15) 0.0021(12) -0.0009(13) 0.0001(12) C12 0.054(3) 0.0225(18) 0.032(2) 0.0027(16) -0.008(2) 0.0036(18) O1 0.0369(15) 0.0458(16) 0.0225(13) 0.0013(12) 0.0003(12) 0.0109(13) C13 0.042(2) 0.047(2) 0.0161(17) 0.0017(16) -0.0034(16) 0.0030(19) C14 0.037(2) 0.045(2) 0.0166(18) -0.0047(16) -0.0009(16) -0.0004(18) O2 0.0331(14) 0.0365(15) 0.0214(13) -0.0076(11) -0.0007(11) 0.0070(12) C15 0.037(2) 0.039(2) 0.0253(19) -0.0085(17) 0.0075(17) 0.0090(18) C16 0.033(2) 0.041(2) 0.032(2) -0.0092(17) 0.0152(18) 0.0025(18) O3 0.0206(12) 0.0456(16) 0.0266(14) -0.0121(11) 0.0010(11) 0.0037(11) C17 0.0242(19) 0.051(2) 0.041(2) -0.013(2) 0.0000(18) 0.0073(18) C18 0.0195(18) 0.053(3) 0.033(2) -0.0112(19) 0.0055(16) -0.0009(17) O4 0.0226(13) 0.0374(15) 0.0335(14) -0.0105(12) 0.0068(12) -0.0017(11) C19 0.0195(17) 0.0297(18) 0.0251(18) -0.0018(14) -0.0035(14) 0.0034(14) C20 0.0249(19) 0.048(2) 0.027(2) 0.0104(17) -0.0067(16) -0.0010(17) C21 0.030(2) 0.0247(19) 0.050(3) 0.0058(17) -0.0175(19) 0.0014(16) C22 0.033(2) 0.029(2) 0.039(2) -0.0018(17) -0.0151(18) 0.0047(16) C23 0.0233(18) 0.035(2) 0.032(2) -0.0069(16) -0.0108(16) 0.0111(15) C24 0.0242(18) 0.0284(19) 0.0263(18) -0.0006(15) -0.0058(15) 0.0008(15) O5 0.0254(13) 0.0289(13) 0.0330(14) -0.0053(11) 0.0056(11) -0.0013(11) C25 0.031(2) 0.044(2) 0.028(2) -0.0023(17) 0.0005(17) 0.0013(17) C26 0.034(2) 0.042(2) 0.034(2) 0.0076(18) -0.0046(18) -0.0061(18) O6 0.0286(14) 0.0330(14) 0.0330(14) 0.0064(11) -0.0006(12) -0.0058(12) C27 0.037(2) 0.0285(19) 0.034(2) 0.0139(16) 0.0023(17) -0.0001(17) C28 0.029(2) 0.038(2) 0.034(2) 0.0100(17) 0.0100(17) -0.0068(17) O7 0.0307(14) 0.0424(16) 0.0337(15) 0.0081(12) 0.0019(12) -0.0102(12) C29 0.038(2) 0.057(3) 0.040(3) -0.002(2) -0.003(2) 0.000(2) C30 0.050(3) 0.064(3) 0.042(3) -0.003(2) -0.001(2) 0.002(2) O8 0.0501(19) 0.064(2) 0.0289(16) 0.0083(15) 0.0039(14) 0.0049(17) C31 0.039(2) 0.061(3) 0.025(2) -0.0111(19) -0.0073(18) 0.009(2) C32 0.051(3) 0.073(3) 0.028(2) -0.014(2) -0.004(2) 0.010(3) C33 0.042(3) 0.089(4) 0.039(3) -0.026(3) -0.011(2) 0.020(3) C34 0.058(3) 0.058(3) 0.047(3) -0.014(2) -0.024(3) 0.019(3) C35 0.045(3) 0.054(3) 0.029(2) -0.008(2) -0.0149(19) 0.013(2) C36 0.041(2) 0.046(2) 0.0193(18) -0.0040(16) -0.0065(16) 0.0063(19) O9 0.0271(14) 0.0317(14) 0.0334(15) 0.0019(11) -0.0068(11) -0.0003(11) C37 0.043(2) 0.064(3) 0.029(2) -0.002(2) -0.0072(19) -0.022(2) C38 0.081(4) 0.104(5) 0.042(3) -0.026(3) 0.027(3) -0.060(4) O10 0.0487(19) 0.100(3) 0.0290(16) -0.0198(17) 0.0091(15) -0.050(2) C39 0.039(2) 0.0243(18) 0.031(2) -0.0005(15) -0.0033(17) -0.0068(16) C40 0.037(2) 0.066(3) 0.033(2) -0.013(2) -0.0042(19) -0.018(2) O11 0.0514(19) 0.0460(17) 0.0403(18) -0.0114(14) 0.0019(15) -0.0176(15) C41 0.039(2) 0.066(3) 0.031(2) 0.003(2) -0.0044(19) -0.021(2) C42 0.036(2) 0.063(3) 0.036(2) 0.007(2) -0.0069(19) -0.008(2) O12 0.0405(16) 0.0527(18) 0.0283(15) 0.0036(13) -0.0079(13) -0.0106(14) C43 0.049(3) 0.051(3) 0.025(2) -0.0008(19) 0.0084(19) -0.011(2) C44 0.069(4) 0.063(3) 0.050(3) 0.008(3) 0.015(3) -0.017(3) C45 0.085(5) 0.058(3) 0.075(4) -0.003(3) 0.026(4) 0.003(3) C46 0.073(4) 0.071(4) 0.059(4) -0.015(3) 0.013(3) -0.020(3) C47 0.058(3) 0.064(3) 0.047(3) -0.006(2) 0.009(2) -0.013(3) C48 0.068(3) 0.064(3) 0.0171(19) -0.0019(19) 0.009(2) -0.037(3) O13 0.0495(19) 0.071(2) 0.0298(16) 0.0091(15) -0.0066(15) -0.0160(18) C49 0.070(4) 0.081(4) 0.023(2) 0.007(2) 0.001(2) -0.023(3) C50 0.056(3) 0.070(3) 0.043(3) 0.028(3) -0.004(2) -0.009(3) O14 0.054(2) 0.0525(19) 0.0376(17) 0.0063(14) -0.0032(15) -0.0090(16) C51 0.055(3) 0.058(3) 0.027(2) 0.005(2) -0.009(2) 0.014(2) C52 0.039(2) 0.035(2) 0.043(2) 0.0091(18) -0.020(2) -0.0035(18) O15 0.0318(16) 0.087(3) 0.0404(18) 0.0216(17) -0.0070(14) 0.0131(16) C53 0.028(2) 0.045(2) 0.048(3) 0.011(2) -0.0070(18) 0.0089(18) C54 0.027(2) 0.059(3) 0.044(3) 0.005(2) -0.0085(19) 0.005(2) O16 0.0273(14) 0.0474(17) 0.0349(16) 0.0045(13) -0.0044(12) 0.0057(13) C55 0.0201(18) 0.042(2) 0.0232(18) -0.0039(16) 0.0028(15) 0.0012(15) C56 0.0202(18) 0.047(2) 0.035(2) -0.0124(18) 0.0052(16) -0.0008(16) C57 0.045(3) 0.031(2) 0.047(3) 0.0012(18) 0.022(2) 0.0122(18) C58 0.039(2) 0.034(2) 0.047(3) 0.0030(19) 0.013(2) 0.0084(18) C59 0.035(2) 0.038(2) 0.038(2) 0.0028(18) 0.0122(18) 0.0086(18) C60 0.0185(17) 0.035(2) 0.028(2) -0.0037(16) 0.0018(15) -0.0017(15) P1 0.0311(5) 0.0392(5) 0.0181(4) 0.0009(4) 0.0005(4) -0.0052(4) F1 0.069(2) 0.111(3) 0.0341(15) 0.0242(16) -0.0130(14) -0.050(2) F2 0.087(2) 0.084(2) 0.0436(17) 0.0213(16) 0.0138(17) -0.028(2) F7 0.054(2) 0.117(3) 0.087(3) 0.022(2) -0.0125(19) 0.027(2) P2 0.0527(8) 0.1244(14) 0.0304(6) -0.0100(8) -0.0050(7) 0.0465(9) F8 0.079(3) 0.161(4) 0.096(3) -0.049(3) -0.049(3) 0.038(3) F9 0.059(2) 0.114(3) 0.082(3) 0.005(2) 0.0051(19) 0.046(2) F10 0.090(3) 0.099(3) 0.0384(16) -0.0071(16) 0.0044(17) 0.007(2) F11 0.099(3) 0.127(4) 0.070(2) -0.041(2) -0.023(2) 0.058(3) F12 0.126(4) 0.216(6) 0.045(2) 0.022(3) 0.020(2) 0.110(4) O21 0.054(7) 0.054(7) 0.054(7) 0.009(5) -0.011(5) -0.016(5) O22 0.065(12) 0.080(13) 0.133(19) 0.031(12) 0.025(11) 0.009(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.345(5) . ? C1 C2 1.371(5) . ? C1 H1 0.9500 . ? C2 C3 1.384(5) . ? C2 H2 0.9500 . ? C3 C4 1.391(5) . ? C3 C9 1.472(5) . ? C4 C5 1.366(5) . ? C4 H4 0.9500 . ? C5 N1 1.344(5) . ? C5 H5 0.9500 . ? N1 C6 1.472(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.341(5) . ? C7 C8 1.367(5) . ? C7 H7 0.9500 . ? C8 C9 1.387(5) . ? C8 H8 0.9500 . ? C9 C10 1.390(5) . ? C10 C11 1.362(5) . ? C10 H10 0.9500 . ? C11 N2 1.344(5) . ? C11 H11 0.9500 . ? N2 C12 1.475(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O1 C36 1.365(5) . ? O1 C13 1.445(5) . ? C13 C14 1.480(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O2 1.419(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O2 C15 1.427(5) . ? C15 C16 1.493(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O3 1.430(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O3 C17 1.431(5) . ? C17 C18 1.490(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O4 1.434(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O4 C19 1.375(4) . ? C19 C20 1.368(6) . ? C19 C24 1.415(5) . ? C20 C21 1.380(6) . ? C20 H20 0.9500 . ? C21 C22 1.378(6) . ? C21 H21 0.9500 . ? C22 C23 1.413(6) . ? C22 H22 0.9500 . ? C23 C24 1.384(5) . ? C23 H23 0.9500 . ? C24 O5 1.368(5) . ? O5 C25 1.430(5) . ? C25 C26 1.499(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O6 1.425(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? O6 C27 1.409(5) . ? C27 C28 1.496(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O7 1.404(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? O7 C29 1.448(6) . ? C29 C30 1.495(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O8 1.439(6) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? O8 C31 1.376(6) . ? C31 C32 1.378(7) . ? C31 C36 1.410(7) . ? C32 C33 1.389(8) . ? C32 H32 0.9500 . ? C33 C34 1.373(8) . ? C33 H33 0.9500 . ? C34 C35 1.381(7) . ? C34 H34 0.9500 . ? C35 C36 1.383(7) . ? C35 H35 0.9500 . ? O9 C60 1.358(5) . ? O9 C37 1.428(5) . ? C37 C38 1.470(8) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O10 1.434(6) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? O10 C39 1.396(5) . ? C39 C40 1.478(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O11 1.366(6) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? O11 C41 1.409(5) . ? C41 C42 1.462(7) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 O12 1.440(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? O12 C43 1.368(6) . ? C43 C44 1.363(8) . ? C43 C48 1.452(7) . ? C44 C45 1.418(9) . ? C44 H44 0.9500 . ? C45 C46 1.358(10) . ? C45 H45 0.9500 . ? C46 C47 1.354(9) . ? C46 H46 0.9500 . ? C47 C48 1.366(7) . ? C47 H47 0.9500 . ? C48 O13 1.360(7) . ? O13 C49 1.467(6) . ? C49 C50 1.478(9) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 O14 1.441(6) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? O14 C51 1.379(6) . ? C51 C52 1.473(7) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 O15 1.399(5) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? O15 C53 1.387(5) . ? C53 C54 1.485(6) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 O16 1.444(5) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? O16 C55 1.337(5) . ? C55 C60 1.415(5) . ? C55 C56 1.427(6) . ? C56 C57 1.380(7) . ? C56 H56 0.9500 . ? C57 C58 1.343(7) . ? C57 H57 0.9500 . ? C58 C59 1.377(6) . ? C58 H58 0.9500 . ? C59 C60 1.383(6) . ? C59 H59 0.9500 . ? P1 F23 1.521(10) . ? P1 F16 1.524(9) . ? P1 F4 1.551(9) . ? P1 F24 1.564(13) . ? P1 F13 1.572(9) . ? P1 F2 1.575(3) . ? P1 F1 1.575(3) . ? P1 F5 1.592(6) . ? P1 F15 1.614(8) . ? P1 F6 1.621(9) . ? P1 F26 1.632(10) . ? P1 F3 1.636(6) . ? F7 P2 1.598(4) . ? P2 F10 1.567(4) . ? P2 F9 1.586(4) . ? P2 F8 1.588(4) . ? P2 F11 1.588(4) . ? P2 F12 1.599(4) . ? 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 N1 C1 C2 120.5(3) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 118.5(3) . . ? C2 C3 C9 121.7(3) . . ? C4 C3 C9 119.7(3) . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 120.2(3) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 N1 C1 121.1(3) . . ? C5 N1 C6 119.7(3) . . ? C1 N1 C6 119.2(3) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 120.1(3) . . ? N2 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 118.0(3) . . ? C8 C9 C3 120.2(3) . . ? C10 C9 C3 121.8(3) . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N2 C11 C10 120.2(3) . . ? N2 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C7 N2 C11 121.3(3) . . ? C7 N2 C12 119.2(3) . . ? C11 N2 C12 119.5(3) . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C36 O1 C13 116.1(3) . . ? O1 C13 C14 108.4(3) . . ? O1 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? O1 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? O2 C14 C13 108.6(3) . . ? O2 C14 H14A 110.0 . . ? C13 C14 H14A 110.0 . . ? O2 C14 H14B 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.3 . . ? C14 O2 C15 113.0(3) . . ? O2 C15 C16 108.7(3) . . ? O2 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O2 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.3 . . ? O3 C16 C15 109.2(3) . . ? O3 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? O3 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? C16 O3 C17 112.7(3) . . ? O3 C17 C18 112.9(3) . . ? O3 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? O3 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? O4 C18 C17 107.7(3) . . ? O4 C18 H18A 110.2 . . ? C17 C18 H18A 110.2 . . ? O4 C18 H18B 110.2 . . ? C17 C18 H18B 110.2 . . ? H18A C18 H18B 108.5 . . ? C19 O4 C18 117.2(3) . . ? C20 C19 O4 125.7(4) . . ? C20 C19 C24 120.2(4) . . ? O4 C19 C24 114.0(3) . . ? C19 C20 C21 120.9(4) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 120.0(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.2(4) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 119.5(4) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? O5 C24 C23 125.0(4) . . ? O5 C24 C19 115.8(3) . . ? C23 C24 C19 119.2(4) . . ? C24 O5 C25 116.2(3) . . ? O5 C25 C26 109.5(3) . . ? O5 C25 H25A 109.8 . . ? C26 C25 H25A 109.8 . . ? O5 C25 H25B 109.8 . . ? C26 C25 H25B 109.8 . . ? H25A C25 H25B 108.2 . . ? O6 C26 C25 108.9(3) . . ? O6 C26 H26A 109.9 . . ? C25 C26 H26A 109.9 . . ? O6 C26 H26B 109.9 . . ? C25 C26 H26B 109.9 . . ? H26A C26 H26B 108.3 . . ? C27 O6 C26 112.3(3) . . ? O6 C27 C28 109.6(3) . . ? O6 C27 H27A 109.8 . . ? C28 C27 H27A 109.8 . . ? O6 C27 H27B 109.8 . . ? C28 C27 H27B 109.8 . . ? H27A C27 H27B 108.2 . . ? O7 C28 C27 110.6(3) . . ? O7 C28 H28A 109.5 . . ? C27 C28 H28A 109.5 . . ? O7 C28 H28B 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 108.1 . . ? C28 O7 C29 108.3(3) . . ? O7 C29 C30 107.9(4) . . ? O7 C29 H29A 110.1 . . ? C30 C29 H29A 110.1 . . ? O7 C29 H29B 110.1 . . ? C30 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? O8 C30 C29 114.8(4) . . ? O8 C30 H30A 108.6 . . ? C29 C30 H30A 108.6 . . ? O8 C30 H30B 108.6 . . ? C29 C30 H30B 108.6 . . ? H30A C30 H30B 107.5 . . ? C31 O8 C30 120.6(4) . . ? O8 C31 C32 125.1(5) . . ? O8 C31 C36 115.6(4) . . ? C32 C31 C36 119.3(5) . . ? C31 C32 C33 119.8(5) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C34 C33 C32 120.7(5) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 120.4(5) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 119.7(5) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? O1 C36 C35 125.2(4) . . ? O1 C36 C31 114.7(4) . . ? C35 C36 C31 120.1(4) . . ? C60 O9 C37 115.4(3) . . ? O9 C37 C38 108.9(4) . . ? O9 C37 H37A 109.9 . . ? C38 C37 H37A 109.9 . . ? O9 C37 H37B 109.9 . . ? C38 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? O10 C38 C37 112.8(5) . . ? O10 C38 H38A 109.0 . . ? C37 C38 H38A 109.0 . . ? O10 C38 H38B 109.0 . . ? C37 C38 H38B 109.0 . . ? H38A C38 H38B 107.8 . . ? C39 O10 C38 115.6(4) . . ? O10 C39 C40 112.2(3) . . ? O10 C39 H39A 109.2 . . ? C40 C39 H39A 109.2 . . ? O10 C39 H39B 109.2 . . ? C40 C39 H39B 109.2 . . ? H39A C39 H39B 107.9 . . ? O11 C40 C39 114.9(4) . . ? O11 C40 H40A 108.5 . . ? C39 C40 H40A 108.5 . . ? O11 C40 H40B 108.5 . . ? C39 C40 H40B 108.5 . . ? H40A C40 H40B 107.5 . . ? C40 O11 C41 114.8(4) . . ? O11 C41 C42 107.7(4) . . ? O11 C41 H41A 110.2 . . ? C42 C41 H41A 110.2 . . ? O11 C41 H41B 110.2 . . ? C42 C41 H41B 110.2 . . ? H41A C41 H41B 108.5 . . ? O12 C42 C41 108.1(4) . . ? O12 C42 H42A 110.1 . . ? C41 C42 H42A 110.1 . . ? O12 C42 H42B 110.1 . . ? C41 C42 H42B 110.1 . . ? H42A C42 H42B 108.4 . . ? C43 O12 C42 114.7(4) . . ? C44 C43 O12 127.2(5) . . ? C44 C43 C48 119.8(5) . . ? O12 C43 C48 113.0(4) . . ? C43 C44 C45 120.0(6) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C46 C45 C44 118.1(6) . . ? C46 C45 H45 121.0 . . ? C44 C45 H45 121.0 . . ? C47 C46 C45 123.5(6) . . ? C47 C46 H46 118.3 . . ? C45 C46 H46 118.3 . . ? C46 C47 C48 120.3(6) . . ? C46 C47 H47 119.8 . . ? C48 C47 H47 119.8 . . ? O13 C48 C47 124.0(5) . . ? O13 C48 C43 117.7(4) . . ? C47 C48 C43 118.2(6) . . ? C48 O13 C49 118.1(4) . . ? O13 C49 C50 109.6(4) . . ? O13 C49 H49A 109.7 . . ? C50 C49 H49A 109.7 . . ? O13 C49 H49B 109.7 . . ? C50 C49 H49B 109.7 . . ? H49A C49 H49B 108.2 . . ? O14 C50 C49 113.5(4) . . ? O14 C50 H50A 108.9 . . ? C49 C50 H50A 108.9 . . ? O14 C50 H50B 108.9 . . ? C49 C50 H50B 108.9 . . ? H50A C50 H50B 107.7 . . ? C51 O14 C50 112.3(4) . . ? O14 C51 C52 110.4(4) . . ? O14 C51 H51A 109.6 . . ? C52 C51 H51A 109.6 . . ? O14 C51 H51B 109.6 . . ? C52 C51 H51B 109.6 . . ? H51A C51 H51B 108.1 . . ? O15 C52 C51 112.6(4) . . ? O15 C52 H52A 109.1 . . ? C51 C52 H52A 109.1 . . ? O15 C52 H52B 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? C53 O15 C52 115.5(3) . . ? O15 C53 C54 111.3(4) . . ? O15 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? O15 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? O16 C54 C53 109.5(4) . . ? O16 C54 H54A 109.8 . . ? C53 C54 H54A 109.8 . . ? O16 C54 H54B 109.8 . . ? C53 C54 H54B 109.8 . . ? H54A C54 H54B 108.2 . . ? C55 O16 C54 115.3(3) . . ? O16 C55 C60 116.1(4) . . ? O16 C55 C56 126.1(4) . . ? C60 C55 C56 117.8(4) . . ? C57 C56 C55 119.5(4) . . ? C57 C56 H56 120.3 . . ? C55 C56 H56 120.3 . . ? C58 C57 C56 122.8(4) . . ? C58 C57 H57 118.6 . . ? C56 C57 H57 118.6 . . ? C57 C58 C59 118.2(4) . . ? C57 C58 H58 120.9 . . ? C59 C58 H58 120.9 . . ? C58 C59 C60 123.1(4) . . ? C58 C59 H59 118.4 . . ? C60 C59 H59 118.4 . . ? O9 C60 C59 124.6(4) . . ? O9 C60 C55 116.8(3) . . ? C59 C60 C55 118.5(4) . . ? F23 P1 F24 97.5(7) . . ? F16 P1 F13 90.7(6) . . ? F23 P1 F2 84.0(4) . . ? F16 P1 F2 86.5(4) . . ? F4 P1 F2 96.8(4) . . ? F24 P1 F2 80.0(5) . . ? F13 P1 F2 97.3(4) . . ? F23 P1 F1 95.9(4) . . ? F16 P1 F1 93.4(4) . . ? F4 P1 F1 83.5(4) . . ? F24 P1 F1 100.4(5) . . ? F13 P1 F1 82.4(4) . . ? F2 P1 F1 179.7(2) . . ? F4 P1 F5 93.0(5) . . ? F2 P1 F5 95.5(3) . . ? F1 P1 F5 84.6(3) . . ? F16 P1 F15 89.0(5) . . ? F13 P1 F15 179.3(5) . . ? F2 P1 F15 83.3(3) . . ? F1 P1 F15 97.0(3) . . ? F4 P1 F6 178.1(5) . . ? F2 P1 F6 81.3(4) . . ? F1 P1 F6 98.4(4) . . ? F5 P1 F6 87.4(5) . . ? F23 P1 F26 92.7(6) . . ? F24 P1 F26 169.6(7) . . ? F2 P1 F26 99.2(5) . . ? F1 P1 F26 80.4(5) . . ? F4 P1 F3 92.7(5) . . ? F2 P1 F3 86.3(3) . . ? F1 P1 F3 93.5(3) . . ? F5 P1 F3 173.8(5) . . ? F6 P1 F3 87.0(5) . . ? F10 P2 F9 90.2(2) . . ? F10 P2 F8 89.9(3) . . ? F9 P2 F8 88.9(2) . . ? F10 P2 F11 90.6(2) . . ? F9 P2 F11 178.9(2) . . ? F8 P2 F11 90.3(3) . . ? F10 P2 F7 89.4(2) . . ? F9 P2 F7 89.5(2) . . ? F8 P2 F7 178.3(3) . . ? F11 P2 F7 91.3(2) . . ? F10 P2 F12 177.2(3) . . ? F9 P2 F12 87.5(3) . . ? F8 P2 F12 91.6(3) . . ? F11 P2 F12 91.7(3) . . ? F7 P2 F12 89.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -2.1(5) . . . . ? C1 C2 C3 C4 0.6(5) . . . . ? C1 C2 C3 C9 176.4(3) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C9 C3 C4 C5 -174.6(3) . . . . ? C3 C4 C5 N1 -1.7(6) . . . . ? C4 C5 N1 C1 0.1(5) . . . . ? C4 C5 N1 C6 -179.9(4) . . . . ? C2 C1 N1 C5 1.8(5) . . . . ? C2 C1 N1 C6 -178.2(4) . . . . ? N2 C7 C8 C9 -3.6(5) . . . . ? C7 C8 C9 C10 2.7(5) . . . . ? C7 C8 C9 C3 -174.9(3) . . . . ? C2 C3 C9 C8 -53.5(5) . . . . ? C4 C3 C9 C8 122.3(4) . . . . ? C2 C3 C9 C10 129.1(4) . . . . ? C4 C3 C9 C10 -55.1(5) . . . . ? C8 C9 C10 C11 0.0(5) . . . . ? C3 C9 C10 C11 177.5(3) . . . . ? C9 C10 C11 N2 -1.8(5) . . . . ? C8 C7 N2 C11 1.7(5) . . . . ? C8 C7 N2 C12 -179.2(3) . . . . ? C10 C11 N2 C7 1.0(5) . . . . ? C10 C11 N2 C12 -178.1(3) . . . . ? C36 O1 C13 C14 178.7(3) . . . . ? O1 C13 C14 O2 -78.1(4) . . . . ? C13 C14 O2 C15 179.8(3) . . . . ? C14 O2 C15 C16 162.7(3) . . . . ? O2 C15 C16 O3 66.0(4) . . . . ? C15 C16 O3 C17 -177.1(3) . . . . ? C16 O3 C17 C18 98.2(4) . . . . ? O3 C17 C18 O4 70.2(4) . . . . ? C17 C18 O4 C19 166.6(3) . . . . ? C18 O4 C19 C20 7.8(5) . . . . ? C18 O4 C19 C24 -169.0(3) . . . . ? O4 C19 C20 C21 -175.8(4) . . . . ? C24 C19 C20 C21 0.8(6) . . . . ? C19 C20 C21 C22 -0.4(6) . . . . ? C20 C21 C22 C23 -0.7(6) . . . . ? C21 C22 C23 C24 1.4(6) . . . . ? C22 C23 C24 O5 -179.9(3) . . . . ? C22 C23 C24 C19 -1.0(5) . . . . ? C20 C19 C24 O5 178.9(3) . . . . ? O4 C19 C24 O5 -4.1(5) . . . . ? C20 C19 C24 C23 -0.1(5) . . . . ? O4 C19 C24 C23 176.9(3) . . . . ? C23 C24 O5 C25 -14.0(5) . . . . ? C19 C24 O5 C25 167.1(3) . . . . ? C24 O5 C25 C26 -171.9(3) . . . . ? O5 C25 C26 O6 -76.6(4) . . . . ? C25 C26 O6 C27 -172.3(3) . . . . ? C26 O6 C27 C28 163.4(3) . . . . ? O6 C27 C28 O7 70.3(4) . . . . ? C27 C28 O7 C29 -167.8(4) . . . . ? C28 O7 C29 C30 -167.6(4) . . . . ? O7 C29 C30 O8 -56.2(6) . . . . ? C29 C30 O8 C31 -83.6(5) . . . . ? C30 O8 C31 C32 8.5(6) . . . . ? C30 O8 C31 C36 -169.7(4) . . . . ? O8 C31 C32 C33 179.5(4) . . . . ? C36 C31 C32 C33 -2.4(6) . . . . ? C31 C32 C33 C34 1.8(7) . . . . ? C32 C33 C34 C35 -0.2(7) . . . . ? C33 C34 C35 C36 -0.7(7) . . . . ? C13 O1 C36 C35 -12.1(6) . . . . ? C13 O1 C36 C31 168.2(3) . . . . ? C34 C35 C36 O1 -179.7(4) . . . . ? C34 C35 C36 C31 0.0(6) . . . . ? O8 C31 C36 O1 -0.5(5) . . . . ? C32 C31 C36 O1 -178.7(4) . . . . ? O8 C31 C36 C35 179.8(4) . . . . ? C32 C31 C36 C35 1.5(6) . . . . ? C60 O9 C37 C38 -170.2(4) . . . . ? O9 C37 C38 O10 -78.5(6) . . . . ? C37 C38 O10 C39 -118.4(5) . . . . ? C38 O10 C39 C40 -163.8(5) . . . . ? O10 C39 C40 O11 -58.3(6) . . . . ? C39 C40 O11 C41 -178.5(4) . . . . ? C40 O11 C41 C42 178.0(4) . . . . ? O11 C41 C42 O12 74.8(5) . . . . ? C41 C42 O12 C43 -159.9(4) . . . . ? C42 O12 C43 C44 1.1(6) . . . . ? C42 O12 C43 C48 179.4(3) . . . . ? O12 C43 C44 C45 176.9(5) . . . . ? C48 C43 C44 C45 -1.3(7) . . . . ? C43 C44 C45 C46 1.4(9) . . . . ? C44 C45 C46 C47 -0.7(10) . . . . ? C45 C46 C47 C48 -0.2(9) . . . . ? C46 C47 C48 O13 -179.8(5) . . . . ? C46 C47 C48 C43 0.3(7) . . . . ? C44 C43 C48 O13 -179.5(4) . . . . ? O12 C43 C48 O13 2.1(5) . . . . ? C44 C43 C48 C47 0.4(6) . . . . ? O12 C43 C48 C47 -178.0(4) . . . . ? C47 C48 O13 C49 -16.3(6) . . . . ? C43 C48 O13 C49 163.6(4) . . . . ? C48 O13 C49 C50 -179.0(4) . . . . ? O13 C49 C50 O14 -85.8(5) . . . . ? C49 C50 O14 C51 -85.0(5) . . . . ? C50 O14 C51 C52 -178.4(4) . . . . ? O14 C51 C52 O15 -64.6(5) . . . . ? C51 C52 O15 C53 174.3(4) . . . . ? C52 O15 C53 C54 163.6(4) . . . . ? O15 C53 C54 O16 71.6(5) . . . . ? C53 C54 O16 C55 -177.7(3) . . . . ? C54 O16 C55 C60 -174.0(3) . . . . ? C54 O16 C55 C56 5.7(5) . . . . ? O16 C55 C56 C57 -178.4(4) . . . . ? C60 C55 C56 C57 1.3(5) . . . . ? C55 C56 C57 C58 0.0(6) . . . . ? C56 C57 C58 C59 -1.4(6) . . . . ? C57 C58 C59 C60 1.6(6) . . . . ? C37 O9 C60 C59 -11.4(5) . . . . ? C37 O9 C60 C55 167.1(4) . . . . ? C58 C59 C60 O9 178.2(4) . . . . ? C58 C59 C60 C55 -0.4(6) . . . . ? O16 C55 C60 O9 0.0(5) . . . . ? C56 C55 C60 O9 -179.7(3) . . . . ? O16 C55 C60 C59 178.6(3) . . . . ? C56 C55 C60 C59 -1.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.183 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.091 #===END data_mjm303 _database_code_depnum_ccdc_archive 'CCDC 721645' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N2, 2 (C24 H32 O8), 2 (F6 P), 2 (H2 O)' _chemical_formula_sum 'C68 H98 N2 O18 F12 P2' _chemical_formula_weight 1521.42 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' _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 16.5359(10) _cell_length_b 14.4572(9) _cell_length_c 31.097(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.492(1) _cell_angle_gamma 90.00 _cell_volume 7420.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6406 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 19.75 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3208 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8799 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.034 before and 0.028 after correction. The Ratio of minimum to maximum transmission is 0.884011. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; The hydrogen atoms of the solvent water could not be detected. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31417 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 19.84 _reflns_number_total 6741 _reflns_number_gt 5608 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0492P)^2^+17.0310P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6741 _refine_ls_number_parameters 926 _refine_ls_number_restraints 238 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7160(3) 0.3228(3) 0.08291(13) 0.0258(11) Uani 1 1 d U . . H1 H 0.6760 0.2894 0.0660 0.031 Uiso 1 1 calc R . . C2 C 0.6974(3) 0.4060(3) 0.09989(13) 0.0250(11) Uani 1 1 d U . . H2 H 0.6439 0.4296 0.0957 0.030 Uiso 1 1 calc R . . C3 C 0.7562(3) 0.4567(3) 0.12342(13) 0.0216(10) Uani 1 1 d U . . C4 C 0.8333(3) 0.4192(3) 0.12833(13) 0.0245(11) Uani 1 1 d U . . H4 H 0.8755 0.4530 0.1433 0.029 Uiso 1 1 calc R . . C5 C 0.8493(3) 0.3345(3) 0.11184(13) 0.0259(11) Uani 1 1 d U . . H5 H 0.9020 0.3087 0.1160 0.031 Uiso 1 1 calc R . . N1 N 0.7905(2) 0.2873(2) 0.08978(10) 0.0238(9) Uani 1 1 d U . . C6 C 0.8090(3) 0.1943(3) 0.07234(14) 0.0285(11) Uani 1 1 d U . . H6A H 0.7580 0.1592 0.0673 0.034 Uiso 1 1 calc R . . H6B H 0.8439 0.1601 0.0939 0.034 Uiso 1 1 calc R . . C7 C 0.8512(3) 0.2006(3) 0.03085(14) 0.0315(12) Uani 1 1 d U . . H7A H 0.9040 0.2322 0.0363 0.038 Uiso 1 1 calc R . . H7B H 0.8180 0.2382 0.0099 0.038 Uiso 1 1 calc R . . C8 C 0.8653(3) 0.1059(3) 0.01176(14) 0.0320(12) Uani 1 1 d U . . H8A H 0.8964 0.0677 0.0334 0.038 Uiso 1 1 calc R . . H8B H 0.8122 0.0756 0.0054 0.038 Uiso 1 1 calc R . . C9 C 0.9103(3) 0.1089(4) -0.02886(15) 0.0487(14) Uani 1 1 d U . . H9A H 0.9650 0.1348 -0.0221 0.058 Uiso 1 1 calc R . . H9B H 0.8814 0.1509 -0.0497 0.058 Uiso 1 1 calc R . . C10 C 0.9187(3) 0.0150(4) -0.04956(16) 0.0574(16) Uani 1 1 d U . . H10A H 0.9499 -0.0260 -0.0297 0.086 Uiso 1 1 calc R . . H10B H 0.9468 0.0216 -0.0762 0.086 Uiso 1 1 calc R . . H10C H 0.8648 -0.0115 -0.0561 0.086 Uiso 1 1 calc R . . C11 C 0.7637(3) 0.7063(3) 0.15445(14) 0.0286(11) Uani 1 1 d U . . H11 H 0.7959 0.7595 0.1501 0.034 Uiso 1 1 calc R . . C12 C 0.7849(3) 0.6229(3) 0.13709(13) 0.0228(11) Uani 1 1 d U . . H12 H 0.8321 0.6180 0.1213 0.027 Uiso 1 1 calc R . . C13 C 0.7370(2) 0.5463(3) 0.14276(13) 0.0221(10) Uani 1 1 d U . . C14 C 0.6700(3) 0.5552(3) 0.16730(13) 0.0272(11) Uani 1 1 d U . . H14 H 0.6364 0.5033 0.1719 0.033 Uiso 1 1 calc R . . C15 C 0.6527(3) 0.6392(3) 0.18475(14) 0.0289(11) Uani 1 1 d U . . H15 H 0.6079 0.6450 0.2023 0.035 Uiso 1 1 calc R . . N2 N 0.6981(2) 0.7130(3) 0.17748(11) 0.0302(9) Uani 1 1 d U . . C16 C 0.6761(3) 0.8051(3) 0.19483(16) 0.0463(14) Uani 1 1 d U . . H16A H 0.6164 0.8111 0.1937 0.056 Uiso 1 1 calc R . . H16B H 0.6975 0.8543 0.1765 0.056 Uiso 1 1 calc R . . C17 C 0.7092(3) 0.8177(4) 0.24010(17) 0.0566(16) Uani 1 1 d U A . H17A H 0.7681 0.8046 0.2417 0.068 Uiso 1 1 calc R . . H17B H 0.6831 0.7728 0.2589 0.068 Uiso 1 1 calc R . . C18 C 0.6955(3) 0.9143(4) 0.2565(2) 0.0696(19) Uani 1 1 d U . . H18A H 0.6870 0.9532 0.2304 0.084 Uiso 0.346(14) 1 calc PR A 1 H18B H 0.6427 0.9120 0.2698 0.084 Uiso 0.346(14) 1 calc PR A 1 H18C H 0.6388 0.9329 0.2489 0.084 Uiso 0.654(14) 1 d PR A 2 H18D H 0.7316 0.9580 0.2424 0.084 Uiso 0.654(14) 1 d PR A 2 C19A C 0.7467(10) 0.9663(11) 0.2852(5) 0.049(6) Uiso 0.346(14) 1 d PU A 1 H19A H 0.7233 1.0284 0.2894 0.059 Uiso 0.346(14) 1 calc PR A 1 H19B H 0.8006 0.9739 0.2734 0.059 Uiso 0.346(14) 1 calc PR A 1 C20A C 0.755(2) 0.914(2) 0.3276(10) 0.113(10) Uiso 0.346(14) 1 d PU A 1 H20A H 0.7584 0.9588 0.3515 0.170 Uiso 0.346(14) 1 calc PR A 1 H20B H 0.8037 0.8761 0.3286 0.170 Uiso 0.346(14) 1 calc PR A 1 H20C H 0.7072 0.8748 0.3303 0.170 Uiso 0.346(14) 1 calc PR A 1 C19B C 0.7131(6) 0.9201(7) 0.3079(3) 0.062(4) Uiso 0.654(14) 1 d PU A 2 H19C H 0.7085 0.9854 0.3170 0.074 Uiso 0.654(14) 1 calc PR A 2 H19D H 0.6709 0.8844 0.3220 0.074 Uiso 0.654(14) 1 calc PR A 2 C20B C 0.7889(6) 0.8868(7) 0.3225(3) 0.048(3) Uiso 0.654(14) 1 d PU A 2 H20D H 0.7898 0.8193 0.3196 0.072 Uiso 0.654(14) 1 calc PR A 2 H20E H 0.7996 0.9036 0.3528 0.072 Uiso 0.654(14) 1 calc PR A 2 H20F H 0.8306 0.9139 0.3053 0.072 Uiso 0.654(14) 1 calc PR A 2 O1 O 0.82171(18) 0.4421(2) 0.01257(9) 0.0346(8) Uani 1 1 d U B . C21 C 0.8615(3) 0.5200(3) 0.02807(14) 0.0313(11) Uani 1 1 d U . . C22 C 0.8313(3) 0.6081(4) 0.02325(14) 0.0376(12) Uani 1 1 d U . . H22 H 0.7793 0.6169 0.0091 0.045 Uiso 1 1 calc R . . C23 C 0.8747(3) 0.6840(4) 0.03846(15) 0.0468(14) Uani 1 1 d U . . H23 H 0.8528 0.7444 0.0348 0.056 Uiso 1 1 calc R . . C24 C 0.9496(4) 0.6716(4) 0.05892(16) 0.0510(15) Uani 1 1 d U . . H24 H 0.9801 0.7237 0.0692 0.061 Uiso 1 1 calc R . . C25 C 0.9810(3) 0.5837(4) 0.06463(15) 0.0478(14) Uani 1 1 d U . . H25 H 1.0327 0.5757 0.0791 0.057 Uiso 1 1 calc R . . C26 C 0.9378(3) 0.5066(4) 0.04942(15) 0.0387(12) Uani 1 1 d U . . O2 O 0.96366(18) 0.4169(2) 0.05344(10) 0.0431(9) Uani 1 1 d U . . C27 C 1.0447(3) 0.4044(4) 0.07131(17) 0.0542(15) Uani 1 1 d U B . H27A H 1.0506 0.4328 0.1003 0.065 Uiso 1 1 calc R . . H27B H 1.0833 0.4351 0.0528 0.065 Uiso 1 1 calc R . . C28 C 1.0628(3) 0.3048(4) 0.07431(18) 0.0617(17) Uani 1 1 d U . . H28A H 1.0388 0.2717 0.0488 0.074 Uiso 0.835(11) 1 calc PR B 1 H28B H 1.1221 0.2942 0.0762 0.074 Uiso 0.835(11) 1 calc PR B 1 H28C H 1.1143 0.3016 0.0923 0.074 Uiso 0.165(11) 1 d PR B 2 H28D H 1.0770 0.2880 0.0448 0.074 Uiso 0.165(11) 1 d PR B 2 O3A O 1.0272(2) 0.2732(3) 0.11306(13) 0.0374(18) Uani 0.835(11) 1 d PU B 1 O3B O 1.0133(10) 0.2146(14) 0.0911(6) 0.015(7) Uiso 0.165(11) 1 d PU B 2 C29 C 1.0474(3) 0.1832(4) 0.1230(2) 0.0560(16) Uani 1 1 d U . . H29A H 1.1071 0.1783 0.1270 0.067 Uiso 0.835(11) 1 calc PR B 1 H29B H 1.0296 0.1433 0.0984 0.067 Uiso 0.835(11) 1 calc PR B 1 H29C H 1.0885 0.2286 0.1339 0.067 Uiso 0.165(11) 1 d PR B 2 H29D H 1.0782 0.1303 0.1122 0.067 Uiso 0.165(11) 1 d PR B 2 C30 C 1.0118(3) 0.1483(4) 0.16169(17) 0.0447(14) Uani 1 1 d U B . H30A H 1.0256 0.0820 0.1652 0.054 Uiso 1 1 calc R . . H30B H 1.0360 0.1817 0.1871 0.054 Uiso 1 1 calc R . . O4 O 0.92868(19) 0.1580(3) 0.16051(11) 0.0576(11) Uani 1 1 d U . . C31 C 0.8892(3) 0.1240(4) 0.19586(16) 0.0478(14) Uani 1 1 d U B . H31A H 0.9294 0.1146 0.2204 0.057 Uiso 1 1 calc R . . H31B H 0.8648 0.0632 0.1883 0.057 Uiso 1 1 calc R . . C32 C 0.8257(3) 0.1867(4) 0.20910(15) 0.0455(14) Uani 1 1 d U . . H32A H 0.8073 0.1669 0.2374 0.055 Uiso 1 1 calc R B . H32B H 0.8477 0.2502 0.2122 0.055 Uiso 1 1 calc R . . O5 O 0.75770(18) 0.1863(2) 0.17732(9) 0.0364(8) Uani 1 1 d U B . C33 C 0.6933(3) 0.2416(3) 0.18655(15) 0.0318(12) Uani 1 1 d U . . C34 C 0.6934(3) 0.3015(3) 0.22084(15) 0.0346(12) Uani 1 1 d U B . H34 H 0.7404 0.3066 0.2399 0.042 Uiso 1 1 calc R . . C35 C 0.6257(3) 0.3548(3) 0.22795(16) 0.0383(12) Uani 1 1 d U . . H35 H 0.6264 0.3955 0.2519 0.046 Uiso 1 1 calc R B . C36 C 0.5579(3) 0.3489(3) 0.20059(16) 0.0406(13) Uani 1 1 d U B . H36 H 0.5117 0.3857 0.2055 0.049 Uiso 1 1 calc R . . C37 C 0.5568(3) 0.2896(3) 0.16606(16) 0.0376(12) Uani 1 1 d U . . H37 H 0.5097 0.2859 0.1470 0.045 Uiso 1 1 calc R B . C38 C 0.6234(3) 0.2350(3) 0.15859(15) 0.0353(12) Uani 1 1 d U B . O6 O 0.62800(18) 0.1743(2) 0.12498(10) 0.0430(9) Uani 1 1 d U . . C39 C 0.5546(3) 0.1661(4) 0.09677(16) 0.0568(16) Uani 1 1 d U B . H39A H 0.5106 0.1382 0.1127 0.068 Uiso 1 1 calc R . . H39B H 0.5367 0.2281 0.0865 0.068 Uiso 1 1 calc R . . C40 C 0.5723(3) 0.1081(4) 0.06049(17) 0.0562(15) Uani 1 1 d U . . H40A H 0.5980 0.0503 0.0715 0.067 Uiso 1 1 calc R B . H40B H 0.5207 0.0913 0.0446 0.067 Uiso 1 1 calc R . . O7 O 0.62434(18) 0.1511(2) 0.03125(9) 0.0385(8) Uani 1 1 d U B . C41 C 0.5841(3) 0.1948(4) -0.00520(16) 0.0425(13) Uani 1 1 d U . . H41A H 0.5467 0.2430 0.0045 0.051 Uiso 1 1 calc R B . H41B H 0.5518 0.1486 -0.0223 0.051 Uiso 1 1 calc R . . C42 C 0.6451(3) 0.2377(3) -0.03245(15) 0.0398(13) Uani 1 1 d U B . H42A H 0.6885 0.1926 -0.0375 0.048 Uiso 1 1 calc R . . H42B H 0.6189 0.2555 -0.0607 0.048 Uiso 1 1 calc R . . O8 O 0.67882(18) 0.3174(2) -0.01134(9) 0.0362(8) Uani 1 1 d U . . C43 C 0.7270(3) 0.3698(3) -0.03868(14) 0.0378(13) Uani 1 1 d U B . H43A H 0.6955 0.3836 -0.0660 0.045 Uiso 1 1 calc R . . H43B H 0.7753 0.3335 -0.0455 0.045 Uiso 1 1 calc R . . C44 C 0.7530(3) 0.4581(3) -0.01721(14) 0.0358(12) Uani 1 1 d U . . H44A H 0.7676 0.5037 -0.0392 0.043 Uiso 1 1 calc R B . H44B H 0.7077 0.4839 -0.0016 0.043 Uiso 1 1 calc R . . O9 O 0.82833(17) 0.6139(2) 0.25244(9) 0.0325(8) Uani 1 1 d U . . C45 C 0.8952(3) 0.5910(3) 0.23138(14) 0.0303(11) Uani 1 1 d U . . C46 C 0.9242(3) 0.5028(4) 0.22805(14) 0.0358(12) Uani 1 1 d U . . H46 H 0.8974 0.4528 0.2409 0.043 Uiso 1 1 calc R . . C47 C 0.9948(3) 0.4866(4) 0.20511(15) 0.0434(13) Uani 1 1 d U . . H47 H 1.0153 0.4258 0.2021 0.052 Uiso 1 1 calc R . . C48 C 1.0326(3) 0.5610(4) 0.18746(15) 0.0480(14) Uani 1 1 d U . . H48 H 1.0799 0.5507 0.1722 0.058 Uiso 1 1 calc R . . C49 C 1.0043(3) 0.6491(4) 0.19117(16) 0.0465(14) Uani 1 1 d U . . H49 H 1.0325 0.6990 0.1790 0.056 Uiso 1 1 calc R . . C50 C 0.9355(3) 0.6661(4) 0.21229(14) 0.0325(12) Uani 1 1 d U . . O10 O 0.90205(19) 0.7507(2) 0.21751(10) 0.0437(9) Uani 1 1 d U . . C51 C 0.9476(3) 0.8333(4) 0.20877(18) 0.0564(16) Uani 1 1 d U . . H51A H 0.9286 0.8838 0.2271 0.068 Uiso 1 1 calc R . . H51B H 1.0053 0.8218 0.2175 0.068 Uiso 1 1 calc R . . C52 C 0.9423(3) 0.8642(4) 0.16514(19) 0.0623(16) Uani 1 1 d U . . H52A H 0.9571 0.8130 0.1460 0.075 Uiso 1 1 calc R . . H52B H 0.9809 0.9156 0.1617 0.075 Uiso 1 1 calc R . . O11 O 0.8620(2) 0.8947(2) 0.15329(11) 0.0470(9) Uani 1 1 d U . . C53 C 0.8560(3) 0.9316(4) 0.11123(16) 0.0466(14) Uani 1 1 d U . . H53A H 0.8824 0.8892 0.0914 0.056 Uiso 1 1 calc R . . H53B H 0.8846 0.9918 0.1109 0.056 Uiso 1 1 calc R . . C54 C 0.7695(3) 0.9447(3) 0.09624(16) 0.0428(13) Uani 1 1 d U . . H54A H 0.7410 0.9810 0.1177 0.051 Uiso 1 1 calc R . . H54B H 0.7657 0.9786 0.0685 0.051 Uiso 1 1 calc R . . O12 O 0.73379(19) 0.8559(2) 0.09104(10) 0.0400(9) Uani 1 1 d U . . C55 C 0.6602(3) 0.8571(3) 0.06457(16) 0.0401(13) Uani 1 1 d U . . H55A H 0.6696 0.8863 0.0365 0.048 Uiso 1 1 calc R . . H55B H 0.6188 0.8938 0.0787 0.048 Uiso 1 1 calc R . . C56 C 0.6309(3) 0.7609(3) 0.05761(15) 0.0381(12) Uani 1 1 d U . . H56A H 0.5954 0.7575 0.0309 0.046 Uiso 1 1 calc R . . H56B H 0.6775 0.7189 0.0545 0.046 Uiso 1 1 calc R . . O13 O 0.58664(18) 0.7326(2) 0.09387(9) 0.0349(8) Uani 1 1 d U . . C57 C 0.5446(3) 0.6511(3) 0.08992(15) 0.0336(12) Uani 1 1 d U . . C58 C 0.5533(3) 0.5873(3) 0.05759(15) 0.0359(12) Uani 1 1 d U . . H58 H 0.5903 0.5984 0.0359 0.043 Uiso 1 1 calc R . . C59 C 0.5074(3) 0.5064(4) 0.05698(17) 0.0450(13) Uani 1 1 d U . . H59 H 0.5143 0.4614 0.0352 0.054 Uiso 1 1 calc R . . C60 C 0.4525(3) 0.4912(4) 0.08750(18) 0.0487(14) Uani 1 1 d U . . H60 H 0.4210 0.4362 0.0866 0.058 Uiso 1 1 calc R . . C61 C 0.4429(3) 0.5560(4) 0.11969(16) 0.0428(13) Uani 1 1 d U . . H61 H 0.4045 0.5454 0.1407 0.051 Uiso 1 1 calc R . . C62 C 0.4886(3) 0.6355(3) 0.12133(15) 0.0340(12) Uani 1 1 d U . . O14 O 0.48580(18) 0.7032(2) 0.15201(10) 0.0416(9) Uani 1 1 d U . . C63 C 0.4207(3) 0.7022(4) 0.18080(17) 0.0499(14) Uani 1 1 d U . . H63A H 0.3696 0.6871 0.1640 0.060 Uiso 1 1 calc R . . H63B H 0.4148 0.7651 0.1929 0.060 Uiso 1 1 calc R . . C64 C 0.4319(3) 0.6352(4) 0.21717(16) 0.0493(14) Uani 1 1 d U . . H64A H 0.3847 0.6385 0.2353 0.059 Uiso 1 1 calc R . . H64B H 0.4348 0.5716 0.2056 0.059 Uiso 1 1 calc R . . O15 O 0.50377(19) 0.6548(2) 0.24281(11) 0.0431(9) Uani 1 1 d U . . C65 C 0.5139(3) 0.5935(4) 0.27838(16) 0.0456(14) Uani 1 1 d U . . H65A H 0.5141 0.5289 0.2679 0.055 Uiso 1 1 calc R . . H65B H 0.4680 0.6007 0.2971 0.055 Uiso 1 1 calc R . . C66 C 0.5907(3) 0.6130(4) 0.30350(16) 0.0488(14) Uani 1 1 d U . . H66A H 0.5942 0.6797 0.3105 0.059 Uiso 1 1 calc R . . H66B H 0.5926 0.5778 0.3309 0.059 Uiso 1 1 calc R . . O16 O 0.65714(18) 0.5868(2) 0.27891(9) 0.0389(8) Uani 1 1 d U . . C67 C 0.7311(3) 0.5843(4) 0.30484(15) 0.0405(13) Uani 1 1 d U . . H67A H 0.7242 0.5463 0.3308 0.049 Uiso 1 1 calc R . . H67B H 0.7465 0.6477 0.3142 0.049 Uiso 1 1 calc R . . C68 C 0.7960(3) 0.5436(3) 0.27908(15) 0.0348(12) Uani 1 1 d U . . H68A H 0.8398 0.5180 0.2987 0.042 Uiso 1 1 calc R . . H68B H 0.7733 0.4927 0.2608 0.042 Uiso 1 1 calc R . . P1 P 0.31919(8) 0.23805(9) 0.06878(4) 0.0367(4) Uani 1 1 d U . . F1 F 0.37311(16) 0.2595(2) 0.11178(8) 0.0549(8) Uani 1 1 d U . . F2 F 0.26631(17) 0.2170(2) 0.02570(9) 0.0557(8) Uani 1 1 d U . . F3 F 0.25676(17) 0.1829(2) 0.09557(10) 0.0667(9) Uani 1 1 d U . . F4 F 0.27054(17) 0.3305(2) 0.07528(9) 0.0580(8) Uani 1 1 d U . . F5 F 0.38297(19) 0.2932(2) 0.04253(9) 0.0701(10) Uani 1 1 d U . . F6 F 0.36917(19) 0.1460(2) 0.06172(12) 0.0809(11) Uani 1 1 d U . . P2 P 0.80515(8) 0.19141(10) 0.84626(4) 0.0397(4) Uani 1 1 d U . . F7 F 0.72851(15) 0.14691(19) 0.82031(8) 0.0443(7) Uani 1 1 d U . . F8 F 0.88242(16) 0.2349(2) 0.87202(8) 0.0553(8) Uani 1 1 d U . . F9 F 0.85828(16) 0.1690(2) 0.80583(9) 0.0609(9) Uani 1 1 d U . . F10 F 0.8275(2) 0.0917(2) 0.86501(10) 0.0708(10) Uani 1 1 d U . . F11 F 0.75220(18) 0.2115(2) 0.88544(10) 0.0756(11) Uani 1 1 d U . . F12 F 0.78391(18) 0.2886(2) 0.82548(10) 0.0668(9) Uani 1 1 d U . . O17 O 0.3518(3) 0.9598(3) 0.09349(16) 0.1112(17) Uani 1 1 d . . . O18 O 0.4963(3) 0.0854(4) 0.86576(19) 0.1234(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.024(3) 0.033(3) 0.020(3) 0.002(2) -0.003(2) 0.001(2) C2 0.022(3) 0.026(3) 0.026(3) 0.002(2) -0.003(2) 0.002(2) C3 0.025(3) 0.024(3) 0.016(2) 0.003(2) 0.002(2) 0.001(2) C4 0.023(3) 0.029(3) 0.020(3) -0.004(2) -0.004(2) 0.001(2) C5 0.024(3) 0.032(3) 0.022(3) 0.001(2) -0.003(2) 0.003(2) N1 0.030(2) 0.024(2) 0.017(2) -0.0008(17) -0.0034(18) 0.0023(19) C6 0.035(3) 0.024(3) 0.026(3) -0.002(2) -0.002(2) 0.005(2) C7 0.036(3) 0.033(3) 0.026(3) 0.002(2) 0.000(2) 0.007(2) C8 0.035(3) 0.034(3) 0.027(3) 0.002(2) -0.001(2) 0.007(2) C9 0.061(4) 0.054(4) 0.031(3) -0.001(3) 0.005(3) 0.020(3) C10 0.072(4) 0.061(4) 0.039(3) -0.012(3) 0.006(3) 0.025(3) C11 0.029(3) 0.031(3) 0.025(3) 0.003(2) -0.003(2) -0.003(2) C12 0.021(3) 0.029(3) 0.018(3) 0.000(2) -0.002(2) -0.001(2) C13 0.022(3) 0.026(3) 0.018(2) 0.002(2) -0.004(2) 0.000(2) C14 0.026(3) 0.030(3) 0.025(3) 0.003(2) -0.002(2) 0.002(2) C15 0.022(3) 0.039(3) 0.025(3) 0.001(2) 0.003(2) 0.002(2) N2 0.032(2) 0.030(2) 0.028(2) -0.0053(19) 0.0000(19) 0.006(2) C16 0.054(3) 0.038(3) 0.048(3) -0.014(3) 0.008(3) 0.010(3) C17 0.060(4) 0.056(4) 0.054(4) -0.030(3) 0.003(3) 0.004(3) C18 0.057(4) 0.071(4) 0.083(5) -0.044(4) 0.019(3) -0.011(3) O1 0.039(2) 0.037(2) 0.0270(18) 0.0059(16) -0.0069(16) 0.0039(16) C21 0.038(3) 0.037(3) 0.019(3) 0.003(2) 0.001(2) -0.004(2) C22 0.049(3) 0.044(3) 0.020(3) 0.004(2) 0.001(2) -0.006(3) C23 0.067(4) 0.043(3) 0.030(3) 0.002(3) 0.004(3) -0.009(3) C24 0.068(4) 0.053(4) 0.032(3) 0.005(3) 0.007(3) -0.027(3) C25 0.043(3) 0.074(4) 0.025(3) 0.012(3) -0.006(2) -0.019(3) C26 0.042(3) 0.050(3) 0.024(3) 0.017(3) -0.001(2) -0.005(3) O2 0.029(2) 0.063(2) 0.037(2) 0.0158(18) -0.0049(16) 0.0027(18) C27 0.028(3) 0.094(4) 0.041(3) 0.028(3) 0.000(3) -0.003(3) C28 0.023(3) 0.106(5) 0.057(4) 0.042(4) 0.010(3) 0.013(3) O3A 0.030(2) 0.038(3) 0.044(3) 0.007(2) 0.001(2) 0.008(2) C29 0.038(3) 0.051(4) 0.081(5) 0.021(3) 0.016(3) 0.016(3) C30 0.031(3) 0.044(3) 0.058(4) 0.011(3) -0.005(3) 0.008(3) O4 0.031(2) 0.092(3) 0.050(2) 0.035(2) 0.0080(18) 0.020(2) C31 0.040(3) 0.070(4) 0.033(3) 0.014(3) -0.004(3) 0.010(3) C32 0.047(3) 0.064(4) 0.025(3) 0.007(3) -0.007(2) 0.013(3) O5 0.0316(19) 0.052(2) 0.0251(18) 0.0028(16) -0.0038(15) 0.0026(17) C33 0.028(3) 0.041(3) 0.027(3) 0.014(2) 0.000(2) 0.000(2) C34 0.032(3) 0.038(3) 0.034(3) 0.011(2) 0.001(2) -0.001(2) C35 0.043(3) 0.036(3) 0.036(3) 0.007(2) 0.002(3) -0.002(3) C36 0.038(3) 0.044(3) 0.041(3) 0.010(3) 0.008(3) 0.000(3) C37 0.023(3) 0.054(3) 0.036(3) 0.015(3) -0.001(2) -0.005(3) C38 0.041(3) 0.043(3) 0.022(3) 0.005(2) 0.003(2) -0.008(3) O6 0.033(2) 0.064(2) 0.031(2) -0.0003(18) -0.0068(16) -0.0082(17) C39 0.035(3) 0.096(5) 0.040(3) -0.009(3) 0.003(3) -0.017(3) C40 0.049(4) 0.071(4) 0.049(3) -0.013(3) 0.001(3) -0.021(3) O7 0.0305(19) 0.058(2) 0.0267(19) -0.0023(17) -0.0011(16) -0.0090(17) C41 0.031(3) 0.053(3) 0.041(3) -0.010(3) -0.013(3) 0.003(3) C42 0.046(3) 0.046(3) 0.026(3) -0.004(3) -0.010(2) -0.002(3) O8 0.042(2) 0.040(2) 0.0262(18) -0.0039(17) -0.0039(16) 0.0021(16) C43 0.045(3) 0.047(3) 0.020(3) 0.005(2) -0.009(2) 0.008(3) C44 0.040(3) 0.042(3) 0.025(3) 0.006(2) -0.009(2) 0.008(2) O9 0.0300(19) 0.041(2) 0.0266(18) 0.0018(16) 0.0035(15) -0.0016(16) C45 0.026(3) 0.042(3) 0.022(3) 0.000(2) -0.008(2) 0.003(2) C46 0.032(3) 0.051(3) 0.023(3) -0.004(2) -0.008(2) 0.000(3) C47 0.038(3) 0.058(4) 0.032(3) -0.009(3) -0.018(3) 0.014(3) C48 0.039(3) 0.082(4) 0.024(3) -0.001(3) 0.003(2) 0.002(3) C49 0.036(3) 0.068(4) 0.035(3) 0.012(3) 0.000(3) 0.002(3) C50 0.024(3) 0.052(3) 0.021(3) 0.001(2) -0.005(2) -0.005(3) O10 0.037(2) 0.047(2) 0.047(2) 0.0124(18) -0.0025(16) -0.0052(18) C51 0.038(3) 0.059(4) 0.071(4) 0.014(3) -0.005(3) -0.023(3) C52 0.050(4) 0.063(4) 0.073(4) 0.018(3) -0.009(3) -0.017(3) O11 0.045(2) 0.042(2) 0.053(2) 0.0098(18) -0.0134(18) -0.0102(17) C53 0.053(3) 0.038(3) 0.049(3) 0.005(3) 0.000(3) -0.013(3) C54 0.054(3) 0.033(3) 0.041(3) 0.006(3) 0.000(3) -0.007(3) O12 0.046(2) 0.033(2) 0.039(2) 0.0037(16) -0.0092(17) -0.0078(17) C55 0.042(3) 0.042(3) 0.036(3) 0.005(2) -0.007(3) 0.000(2) C56 0.041(3) 0.040(3) 0.033(3) 0.000(2) -0.005(2) 0.005(2) O13 0.0386(19) 0.035(2) 0.0311(19) -0.0052(16) 0.0037(16) -0.0017(16) C57 0.033(3) 0.031(3) 0.035(3) -0.002(2) -0.011(2) 0.001(2) C58 0.041(3) 0.035(3) 0.031(3) -0.002(2) -0.013(2) 0.008(2) C59 0.058(4) 0.035(3) 0.039(3) -0.002(3) -0.022(3) 0.005(3) C60 0.054(4) 0.036(3) 0.052(4) 0.007(3) -0.024(3) -0.006(3) C61 0.040(3) 0.046(3) 0.040(3) 0.008(3) -0.009(3) -0.003(3) C62 0.030(3) 0.035(3) 0.036(3) -0.001(3) -0.002(2) 0.006(2) O14 0.038(2) 0.044(2) 0.043(2) -0.0045(18) 0.0090(17) 0.0050(17) C63 0.033(3) 0.059(4) 0.059(4) -0.004(3) 0.013(3) 0.012(3) C64 0.032(3) 0.071(4) 0.046(3) 0.000(3) 0.009(3) 0.007(3) O15 0.034(2) 0.053(2) 0.043(2) -0.0095(18) 0.0111(17) 0.0020(17) C65 0.037(3) 0.062(4) 0.039(3) -0.006(3) 0.015(3) 0.001(3) C66 0.042(3) 0.070(4) 0.036(3) -0.009(3) 0.012(3) 0.003(3) O16 0.0291(19) 0.059(2) 0.0292(18) -0.0108(17) 0.0067(16) 0.0019(17) C67 0.039(3) 0.052(3) 0.030(3) -0.004(3) 0.004(2) -0.005(3) C68 0.035(3) 0.039(3) 0.030(3) 0.004(2) -0.001(2) -0.007(2) P1 0.0326(8) 0.0407(9) 0.0364(8) 0.0071(7) -0.0010(7) -0.0028(7) F1 0.0398(17) 0.082(2) 0.0410(17) 0.0052(16) -0.0109(14) 0.0020(16) F2 0.0588(19) 0.060(2) 0.0465(18) -0.0037(15) -0.0159(15) -0.0098(16) F3 0.0570(19) 0.082(2) 0.061(2) 0.0304(18) 0.0023(16) -0.0245(17) F4 0.061(2) 0.056(2) 0.0554(19) -0.0025(15) -0.0148(15) 0.0167(16) F5 0.080(2) 0.089(2) 0.0435(18) -0.0123(17) 0.0236(16) -0.0457(19) F6 0.059(2) 0.066(2) 0.116(3) -0.021(2) -0.014(2) 0.0205(18) P2 0.0349(8) 0.0526(10) 0.0319(8) -0.0003(7) 0.0051(7) -0.0058(7) F7 0.0325(16) 0.0587(19) 0.0414(17) -0.0064(14) -0.0005(13) -0.0075(14) F8 0.0424(17) 0.082(2) 0.0403(17) -0.0026(16) -0.0069(14) -0.0214(16) F9 0.0420(17) 0.093(2) 0.0490(19) -0.0165(17) 0.0133(15) -0.0112(17) F10 0.088(2) 0.061(2) 0.059(2) 0.0067(17) -0.0295(18) -0.0038(18) F11 0.066(2) 0.110(3) 0.054(2) -0.0386(19) 0.0325(17) -0.035(2) F12 0.070(2) 0.048(2) 0.080(2) 0.0044(17) -0.0131(18) -0.0099(16) O17 0.141(4) 0.091(4) 0.106(4) -0.013(3) 0.041(3) -0.013(3) O18 0.127(4) 0.101(4) 0.145(5) -0.009(4) 0.030(4) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.339(5) . ? C1 C2 1.357(6) . ? C1 H1 0.9500 . ? C2 C3 1.390(6) . ? C2 H2 0.9500 . ? C3 C4 1.386(6) . ? C3 C13 1.471(6) . ? C4 C5 1.360(6) . ? C4 H4 0.9500 . ? C5 N1 1.341(5) . ? C5 H5 0.9500 . ? N1 C6 1.488(5) . ? C6 C7 1.507(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.516(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.505(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.512(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.340(5) . ? C11 C12 1.375(6) . ? C11 H11 0.9500 . ? C12 C13 1.379(6) . ? C12 H12 0.9500 . ? C13 C14 1.389(6) . ? C14 C15 1.367(6) . ? C14 H14 0.9500 . ? C15 N2 1.331(5) . ? C15 H15 0.9500 . ? N2 C16 1.490(6) . ? C16 C17 1.491(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.508(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19A 1.409(15) . ? C18 C19B 1.611(11) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 H18C 0.9900 . ? C18 H18D 0.9900 . ? C19A C20A 1.52(3) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C19B C20B 1.392(15) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? O1 C21 1.377(5) . ? O1 C44 1.440(5) . ? C21 C22 1.372(6) . ? C21 C26 1.404(7) . ? C22 C23 1.380(7) . ? C22 H22 0.9500 . ? C23 C24 1.370(7) . ? C23 H23 0.9500 . ? C24 C25 1.380(7) . ? C24 H24 0.9500 . ? C25 C26 1.390(7) . ? C25 H25 0.9500 . ? C26 O2 1.369(6) . ? O2 C27 1.431(5) . ? C27 C28 1.472(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O3A 1.447(6) . ? C28 O3B 1.642(18) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 H28C 0.9900 . ? C28 H28D 0.9900 . ? O3A C29 1.374(6) . ? O3B C29 1.202(17) . ? C29 C30 1.460(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29 H29C 0.9900 . ? C29 H29D 0.9900 . ? C30 O4 1.381(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? O4 C31 1.402(6) . ? C31 C32 1.465(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O5 1.451(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? O5 C33 1.376(5) . ? C33 C34 1.374(6) . ? C33 C38 1.406(6) . ? C34 C35 1.388(6) . ? C34 H34 0.9500 . ? C35 C36 1.368(6) . ? C35 H35 0.9500 . ? C36 C37 1.373(7) . ? C36 H36 0.9500 . ? C37 C38 1.386(7) . ? C37 H37 0.9500 . ? C38 O6 1.371(5) . ? O6 C39 1.458(6) . ? C39 C40 1.450(7) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O7 1.432(6) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? O7 C41 1.426(5) . ? C41 C42 1.491(6) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 O8 1.422(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? O8 C43 1.420(5) . ? C43 C44 1.491(6) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? O9 C45 1.361(5) . ? O9 C68 1.435(5) . ? C45 C46 1.367(6) . ? C45 C50 1.423(6) . ? C46 C47 1.424(7) . ? C46 H46 0.9500 . ? C47 C48 1.374(7) . ? C47 H47 0.9500 . ? C48 C49 1.365(7) . ? C48 H48 0.9500 . ? C49 C50 1.370(7) . ? C49 H49 0.9500 . ? C50 O10 1.356(6) . ? O10 C51 1.446(6) . ? C51 C52 1.426(7) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 O11 1.426(6) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? O11 C53 1.411(6) . ? C53 C54 1.489(7) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 O12 1.419(5) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? O12 C55 1.427(5) . ? C55 C56 1.485(6) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 O13 1.440(5) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? O13 C57 1.370(5) . ? C57 C58 1.378(6) . ? C57 C62 1.405(6) . ? C58 C59 1.394(7) . ? C58 H58 0.9500 . ? C59 C60 1.371(7) . ? C59 H59 0.9500 . ? C60 C61 1.388(7) . ? C60 H60 0.9500 . ? C61 C62 1.375(7) . ? C61 H61 0.9500 . ? C62 O14 1.370(5) . ? O14 C63 1.442(5) . ? C63 C64 1.492(7) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 O15 1.419(6) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? O15 C65 1.419(6) . ? C65 C66 1.476(7) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 O16 1.428(5) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? O16 C67 1.423(5) . ? C67 C68 1.499(6) . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C68 H68A 0.9900 . ? C68 H68B 0.9900 . ? P1 F4 1.579(3) . ? P1 F3 1.581(3) . ? P1 F2 1.584(3) . ? P1 F5 1.587(3) . ? P1 F6 1.589(3) . ? P1 F1 1.592(3) . ? P2 F11 1.570(3) . ? P2 F12 1.578(3) . ? P2 F10 1.589(3) . ? P2 F8 1.596(3) . ? P2 F7 1.596(3) . ? P2 F9 1.610(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 N1 C1 C2 120.4(4) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 120.3(4) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 117.5(4) . . ? C4 C3 C13 121.3(4) . . ? C2 C3 C13 121.2(4) . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 120.0(4) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 N1 C5 121.2(4) . . ? C1 N1 C6 119.7(4) . . ? C5 N1 C6 119.2(4) . . ? N1 C6 C7 112.0(3) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 111.8(4) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 113.5(4) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 113.2(4) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 120.4(4) . . ? N2 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.5(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 118.6(4) . . ? C12 C13 C3 121.0(4) . . ? C14 C13 C3 120.3(4) . . ? C15 C14 C13 119.5(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? N2 C15 C14 120.7(4) . . ? N2 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 N2 C11 121.1(4) . . ? C15 N2 C16 120.2(4) . . ? C11 N2 C16 118.7(4) . . ? N2 C16 C17 111.6(4) . . ? N2 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N2 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 112.3(5) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19A C18 C17 127.7(8) . . ? C17 C18 C19B 111.2(6) . . ? C19A C18 H18A 105.4 . . ? C17 C18 H18A 105.4 . . ? C19A C18 H18B 105.4 . . ? C17 C18 H18B 105.4 . . ? H18A C18 H18B 106.0 . . ? C17 C18 H18C 109.3 . . ? C19B C18 H18C 109.6 . . ? C17 C18 H18D 109.5 . . ? C19B C18 H18D 109.1 . . ? H18C C18 H18D 108.0 . . ? C18 C19A C20A 107.7(17) . . ? C18 C19A H19A 110.2 . . ? C20A C19A H19A 110.2 . . ? C18 C19A H19B 110.2 . . ? C20A C19A H19B 110.2 . . ? H19A C19A H19B 108.5 . . ? C20B C19B C18 114.2(8) . . ? C20B C19B H19C 108.7 . . ? C18 C19B H19C 108.7 . . ? C20B C19B H19D 108.7 . . ? C18 C19B H19D 108.7 . . ? H19C C19B H19D 107.6 . . ? C19B C20B H20D 109.5 . . ? C19B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C21 O1 C44 115.8(3) . . ? C22 C21 O1 123.9(4) . . ? C22 C21 C26 119.4(5) . . ? O1 C21 C26 116.7(4) . . ? C21 C22 C23 121.5(5) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 119.5(5) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 120.1(5) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 120.9(5) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? O2 C26 C25 125.2(5) . . ? O2 C26 C21 116.2(4) . . ? C25 C26 C21 118.6(5) . . ? C26 O2 C27 115.8(4) . . ? O2 C27 C28 109.3(5) . . ? O2 C27 H27A 109.8 . . ? C28 C27 H27A 109.8 . . ? O2 C27 H27B 109.8 . . ? C28 C27 H27B 109.8 . . ? H27A C27 H27B 108.3 . . ? O3A C28 C27 105.7(5) . . ? C27 C28 O3B 133.9(7) . . ? O3A C28 H28A 110.6 . . ? C27 C28 H28A 110.6 . . ? O3A C28 H28B 110.6 . . ? C27 C28 H28B 110.6 . . ? O3B C28 H28B 111.7 . . ? H28A C28 H28B 108.7 . . ? C27 C28 H28C 104.2 . . ? O3B C28 H28C 102.2 . . ? C27 C28 H28D 103.9 . . ? O3B C28 H28D 104.4 . . ? H28C C28 H28D 105.5 . . ? C29 O3A C28 112.5(4) . . ? C28 O3A H29C 102.8 . . ? C29 O3B C28 110.2(14) . . ? O3B C29 C30 128.3(8) . . ? O3A C29 C30 114.2(5) . . ? O3A C29 H29A 108.7 . . ? C30 C29 H29A 108.7 . . ? O3A C29 H29B 108.7 . . ? C30 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? O3B C29 H29C 108.0 . . ? C30 C29 H29C 104.5 . . ? O3B C29 H29D 103.6 . . ? C30 C29 H29D 104.9 . . ? H29C C29 H29D 105.7 . . ? O4 C30 C29 113.1(4) . . ? O4 C30 H30A 109.0 . . ? C29 C30 H30A 109.0 . . ? O4 C30 H30B 109.0 . . ? C29 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C30 O4 C31 117.0(4) . . ? O4 C31 C32 112.3(4) . . ? O4 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? O4 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? O5 C32 C31 110.2(4) . . ? O5 C32 H32A 109.6 . . ? C31 C32 H32A 109.6 . . ? O5 C32 H32B 109.6 . . ? C31 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? C33 O5 C32 115.7(3) . . ? C34 C33 O5 124.3(4) . . ? C34 C33 C38 119.0(4) . . ? O5 C33 C38 116.7(4) . . ? C33 C34 C35 120.7(5) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C36 C35 C34 120.3(5) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C37 119.8(5) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C38 120.9(5) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? O6 C38 C37 125.0(4) . . ? O6 C38 C33 115.7(4) . . ? C37 C38 C33 119.3(5) . . ? C38 O6 C39 115.4(4) . . ? C40 C39 O6 108.4(4) . . ? C40 C39 H39A 110.0 . . ? O6 C39 H39A 110.0 . . ? C40 C39 H39B 110.0 . . ? O6 C39 H39B 110.0 . . ? H39A C39 H39B 108.4 . . ? O7 C40 C39 113.6(4) . . ? O7 C40 H40A 108.8 . . ? C39 C40 H40A 108.8 . . ? O7 C40 H40B 108.8 . . ? C39 C40 H40B 108.8 . . ? H40A C40 H40B 107.7 . . ? C41 O7 C40 115.3(4) . . ? O7 C41 C42 109.7(4) . . ? O7 C41 H41A 109.7 . . ? C42 C41 H41A 109.7 . . ? O7 C41 H41B 109.7 . . ? C42 C41 H41B 109.7 . . ? H41A C41 H41B 108.2 . . ? O8 C42 C41 109.5(4) . . ? O8 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? O8 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.2 . . ? C43 O8 C42 112.0(3) . . ? O8 C43 C44 110.2(4) . . ? O8 C43 H43A 109.6 . . ? C44 C43 H43A 109.6 . . ? O8 C43 H43B 109.6 . . ? C44 C43 H43B 109.6 . . ? H43A C43 H43B 108.1 . . ? O1 C44 C43 110.2(4) . . ? O1 C44 H44A 109.6 . . ? C43 C44 H44A 109.6 . . ? O1 C44 H44B 109.6 . . ? C43 C44 H44B 109.6 . . ? H44A C44 H44B 108.1 . . ? C45 O9 C68 116.6(3) . . ? O9 C45 C46 124.2(4) . . ? O9 C45 C50 115.5(4) . . ? C46 C45 C50 120.3(4) . . ? C45 C46 C47 119.5(5) . . ? C45 C46 H46 120.2 . . ? C47 C46 H46 120.2 . . ? C48 C47 C46 118.6(5) . . ? C48 C47 H47 120.7 . . ? C46 C47 H47 120.7 . . ? C49 C48 C47 122.0(5) . . ? C49 C48 H48 119.0 . . ? C47 C48 H48 119.0 . . ? C48 C49 C50 120.5(5) . . ? C48 C49 H49 119.8 . . ? C50 C49 H49 119.8 . . ? O10 C50 C49 125.2(5) . . ? O10 C50 C45 115.7(4) . . ? C49 C50 C45 119.1(5) . . ? C50 O10 C51 120.1(4) . . ? C52 C51 O10 115.8(5) . . ? C52 C51 H51A 108.3 . . ? O10 C51 H51A 108.3 . . ? C52 C51 H51B 108.3 . . ? O10 C51 H51B 108.3 . . ? H51A C51 H51B 107.4 . . ? C51 C52 O11 110.1(5) . . ? C51 C52 H52A 109.6 . . ? O11 C52 H52A 109.6 . . ? C51 C52 H52B 109.6 . . ? O11 C52 H52B 109.6 . . ? H52A C52 H52B 108.1 . . ? C53 O11 C52 111.6(4) . . ? O11 C53 C54 110.5(4) . . ? O11 C53 H53A 109.6 . . ? C54 C53 H53A 109.6 . . ? O11 C53 H53B 109.6 . . ? C54 C53 H53B 109.6 . . ? H53A C53 H53B 108.1 . . ? O12 C54 C53 107.8(4) . . ? O12 C54 H54A 110.1 . . ? C53 C54 H54A 110.1 . . ? O12 C54 H54B 110.1 . . ? C53 C54 H54B 110.1 . . ? H54A C54 H54B 108.5 . . ? C54 O12 C55 112.9(3) . . ? O12 C55 C56 109.3(4) . . ? O12 C55 H55A 109.8 . . ? C56 C55 H55A 109.8 . . ? O12 C55 H55B 109.8 . . ? C56 C55 H55B 109.8 . . ? H55A C55 H55B 108.3 . . ? O13 C56 C55 109.2(4) . . ? O13 C56 H56A 109.9 . . ? C55 C56 H56A 109.9 . . ? O13 C56 H56B 109.9 . . ? C55 C56 H56B 109.9 . . ? H56A C56 H56B 108.3 . . ? C57 O13 C56 116.9(3) . . ? O13 C57 C58 124.5(4) . . ? O13 C57 C62 115.4(4) . . ? C58 C57 C62 120.2(5) . . ? C57 C58 C59 119.4(5) . . ? C57 C58 H58 120.3 . . ? C59 C58 H58 120.3 . . ? C60 C59 C58 120.5(5) . . ? C60 C59 H59 119.7 . . ? C58 C59 H59 119.7 . . ? C59 C60 C61 120.1(5) . . ? C59 C60 H60 120.0 . . ? C61 C60 H60 120.0 . . ? C62 C61 C60 120.3(5) . . ? C62 C61 H61 119.9 . . ? C60 C61 H61 119.9 . . ? O14 C62 C61 125.6(4) . . ? O14 C62 C57 114.9(4) . . ? C61 C62 C57 119.5(5) . . ? C62 O14 C63 118.9(4) . . ? O14 C63 C64 114.5(4) . . ? O14 C63 H63A 108.6 . . ? C64 C63 H63A 108.6 . . ? O14 C63 H63B 108.6 . . ? C64 C63 H63B 108.6 . . ? H63A C63 H63B 107.6 . . ? O15 C64 C63 110.9(4) . . ? O15 C64 H64A 109.5 . . ? C63 C64 H64A 109.5 . . ? O15 C64 H64B 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 108.0 . . ? C65 O15 C64 111.6(4) . . ? O15 C65 C66 110.5(4) . . ? O15 C65 H65A 109.5 . . ? C66 C65 H65A 109.5 . . ? O15 C65 H65B 109.5 . . ? C66 C65 H65B 109.5 . . ? H65A C65 H65B 108.1 . . ? O16 C66 C65 109.3(4) . . ? O16 C66 H66A 109.8 . . ? C65 C66 H66A 109.8 . . ? O16 C66 H66B 109.8 . . ? C65 C66 H66B 109.8 . . ? H66A C66 H66B 108.3 . . ? C67 O16 C66 111.5(3) . . ? O16 C67 C68 109.0(4) . . ? O16 C67 H67A 109.9 . . ? C68 C67 H67A 109.9 . . ? O16 C67 H67B 109.9 . . ? C68 C67 H67B 109.9 . . ? H67A C67 H67B 108.3 . . ? O9 C68 C67 109.6(4) . . ? O9 C68 H68A 109.8 . . ? C67 C68 H68A 109.8 . . ? O9 C68 H68B 109.8 . . ? C67 C68 H68B 109.8 . . ? H68A C68 H68B 108.2 . . ? F4 P1 F3 90.33(18) . . ? F4 P1 F2 90.65(16) . . ? F3 P1 F2 90.25(16) . . ? F4 P1 F5 90.01(18) . . ? F3 P1 F5 179.04(19) . . ? F2 P1 F5 90.64(16) . . ? F4 P1 F6 179.0(2) . . ? F3 P1 F6 90.68(19) . . ? F2 P1 F6 89.28(18) . . ? F5 P1 F6 89.0(2) . . ? F4 P1 F1 89.50(16) . . ? F3 P1 F1 90.34(16) . . ? F2 P1 F1 179.39(18) . . ? F5 P1 F1 88.77(16) . . ? F6 P1 F1 90.56(17) . . ? F11 P2 F12 91.9(2) . . ? F11 P2 F10 90.6(2) . . ? F12 P2 F10 177.29(19) . . ? F11 P2 F8 90.28(16) . . ? F12 P2 F8 90.33(17) . . ? F10 P2 F8 90.69(17) . . ? F11 P2 F7 90.21(16) . . ? F12 P2 F7 90.11(16) . . ? F10 P2 F7 88.85(16) . . ? F8 P2 F7 179.33(19) . . ? F11 P2 F9 178.80(18) . . ? F12 P2 F9 88.74(18) . . ? F10 P2 F9 88.74(18) . . ? F8 P2 F9 90.75(15) . . ? F7 P2 F9 88.75(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.1(6) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C1 C2 C3 C13 -178.9(4) . . . . ? C2 C3 C4 C5 -2.2(6) . . . . ? C13 C3 C4 C5 177.2(4) . . . . ? C3 C4 C5 N1 1.5(6) . . . . ? C2 C1 N1 C5 -3.0(6) . . . . ? C2 C1 N1 C6 177.6(4) . . . . ? C4 C5 N1 C1 1.1(6) . . . . ? C4 C5 N1 C6 -179.5(4) . . . . ? C1 N1 C6 C7 98.9(4) . . . . ? C5 N1 C6 C7 -80.5(5) . . . . ? N1 C6 C7 C8 -176.4(4) . . . . ? C6 C7 C8 C9 -177.7(4) . . . . ? C7 C8 C9 C10 -175.7(4) . . . . ? N2 C11 C12 C13 1.4(6) . . . . ? C11 C12 C13 C14 -2.3(6) . . . . ? C11 C12 C13 C3 177.9(4) . . . . ? C4 C3 C13 C12 49.9(6) . . . . ? C2 C3 C13 C12 -130.7(4) . . . . ? C4 C3 C13 C14 -129.9(4) . . . . ? C2 C3 C13 C14 49.5(6) . . . . ? C12 C13 C14 C15 0.7(6) . . . . ? C3 C13 C14 C15 -179.5(4) . . . . ? C13 C14 C15 N2 1.9(6) . . . . ? C14 C15 N2 C11 -2.9(6) . . . . ? C14 C15 N2 C16 176.9(4) . . . . ? C12 C11 N2 C15 1.2(6) . . . . ? C12 C11 N2 C16 -178.5(4) . . . . ? C15 N2 C16 C17 85.1(5) . . . . ? C11 N2 C16 C17 -95.2(5) . . . . ? N2 C16 C17 C18 173.7(4) . . . . ? C16 C17 C18 C19A -145.5(10) . . . . ? C16 C17 C18 C19B 167.2(6) . . . . ? C17 C18 C19A C20A -62(2) . . . . ? C19B C18 C19A C20A 19.9(16) . . . . ? C19A C18 C19B C20B -69.6(12) . . . . ? C17 C18 C19B C20B 53.2(10) . . . . ? C44 O1 C21 C22 12.5(6) . . . . ? C44 O1 C21 C26 -166.6(4) . . . . ? O1 C21 C22 C23 -178.3(4) . . . . ? C26 C21 C22 C23 0.8(7) . . . . ? C21 C22 C23 C24 -0.1(7) . . . . ? C22 C23 C24 C25 -0.7(7) . . . . ? C23 C24 C25 C26 0.7(7) . . . . ? C24 C25 C26 O2 179.9(4) . . . . ? C24 C25 C26 C21 0.0(7) . . . . ? C22 C21 C26 O2 179.3(4) . . . . ? O1 C21 C26 O2 -1.5(6) . . . . ? C22 C21 C26 C25 -0.7(7) . . . . ? O1 C21 C26 C25 178.4(4) . . . . ? C25 C26 O2 C27 -6.0(6) . . . . ? C21 C26 O2 C27 173.9(4) . . . . ? C26 O2 C27 C28 178.9(4) . . . . ? O2 C27 C28 O3A -80.8(5) . . . . ? O2 C27 C28 O3B -45.2(13) . . . . ? C27 C28 O3A C29 -172.8(4) . . . . ? O3B C28 O3A C29 46.7(9) . . . . ? O3A C28 O3B C29 -55.0(12) . . . . ? C27 C28 O3B C29 -113.2(12) . . . . ? C28 O3B C29 O3A 47.8(9) . . . . ? C28 O3B C29 C30 139.0(8) . . . . ? C28 O3A C29 O3B -58.6(10) . . . . ? C28 O3A C29 C30 -179.3(5) . . . . ? O3B C29 C30 O4 -3.2(16) . . . . ? O3A C29 C30 O4 54.2(7) . . . . ? C29 C30 O4 C31 178.3(5) . . . . ? C30 O4 C31 C32 138.1(5) . . . . ? O4 C31 C32 O5 70.9(6) . . . . ? C31 C32 O5 C33 178.9(4) . . . . ? C32 O5 C33 C34 6.5(6) . . . . ? C32 O5 C33 C38 -173.6(4) . . . . ? O5 C33 C34 C35 -179.8(4) . . . . ? C38 C33 C34 C35 0.2(7) . . . . ? C33 C34 C35 C36 -0.6(7) . . . . ? C34 C35 C36 C37 0.3(7) . . . . ? C35 C36 C37 C38 0.4(7) . . . . ? C36 C37 C38 O6 -179.8(4) . . . . ? C36 C37 C38 C33 -0.8(7) . . . . ? C34 C33 C38 O6 179.6(4) . . . . ? O5 C33 C38 O6 -0.4(6) . . . . ? C34 C33 C38 C37 0.5(7) . . . . ? O5 C33 C38 C37 -179.5(4) . . . . ? C37 C38 O6 C39 -2.5(6) . . . . ? C33 C38 O6 C39 178.5(4) . . . . ? C38 O6 C39 C40 173.5(4) . . . . ? O6 C39 C40 O7 -70.5(6) . . . . ? C39 C40 O7 C41 -95.9(5) . . . . ? C40 O7 C41 C42 179.2(4) . . . . ? O7 C41 C42 O8 -72.2(5) . . . . ? C41 C42 O8 C43 -170.1(4) . . . . ? C42 O8 C43 C44 173.3(4) . . . . ? C21 O1 C44 C43 167.6(4) . . . . ? O8 C43 C44 O1 80.8(5) . . . . ? C68 O9 C45 C46 11.9(6) . . . . ? C68 O9 C45 C50 -167.9(4) . . . . ? O9 C45 C46 C47 179.8(4) . . . . ? C50 C45 C46 C47 -0.4(6) . . . . ? C45 C46 C47 C48 1.0(6) . . . . ? C46 C47 C48 C49 -0.3(7) . . . . ? C47 C48 C49 C50 -1.1(8) . . . . ? C48 C49 C50 O10 -179.5(4) . . . . ? C48 C49 C50 C45 1.8(7) . . . . ? O9 C45 C50 O10 -0.1(5) . . . . ? C46 C45 C50 O10 -179.9(4) . . . . ? O9 C45 C50 C49 178.8(4) . . . . ? C46 C45 C50 C49 -1.0(6) . . . . ? C49 C50 O10 C51 -13.6(7) . . . . ? C45 C50 O10 C51 165.2(4) . . . . ? C50 O10 C51 C52 86.5(6) . . . . ? O10 C51 C52 O11 66.8(6) . . . . ? C51 C52 O11 C53 175.9(4) . . . . ? C52 O11 C53 C54 168.2(4) . . . . ? O11 C53 C54 O12 -67.6(5) . . . . ? C53 C54 O12 C55 -161.6(4) . . . . ? C54 O12 C55 C56 174.9(4) . . . . ? O12 C55 C56 O13 83.1(5) . . . . ? C55 C56 O13 C57 170.2(4) . . . . ? C56 O13 C57 C58 12.1(6) . . . . ? C56 O13 C57 C62 -166.7(4) . . . . ? O13 C57 C58 C59 179.7(4) . . . . ? C62 C57 C58 C59 -1.5(7) . . . . ? C57 C58 C59 C60 1.8(7) . . . . ? C58 C59 C60 C61 -0.8(7) . . . . ? C59 C60 C61 C62 -0.4(7) . . . . ? C60 C61 C62 O14 -178.4(4) . . . . ? C60 C61 C62 C57 0.6(7) . . . . ? O13 C57 C62 O14 -1.6(6) . . . . ? C58 C57 C62 O14 179.5(4) . . . . ? O13 C57 C62 C61 179.2(4) . . . . ? C58 C57 C62 C61 0.3(7) . . . . ? C61 C62 O14 C63 -12.1(6) . . . . ? C57 C62 O14 C63 168.8(4) . . . . ? C62 O14 C63 C64 79.5(5) . . . . ? O14 C63 C64 O15 59.4(6) . . . . ? C63 C64 O15 C65 178.1(4) . . . . ? C64 O15 C65 C66 177.7(4) . . . . ? O15 C65 C66 O16 -69.5(5) . . . . ? C65 C66 O16 C67 -166.8(4) . . . . ? C66 O16 C67 C68 172.0(4) . . . . ? C45 O9 C68 C67 171.5(3) . . . . ? O16 C67 C68 O9 82.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 19.84 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.677 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.051