data_all_cif _journal_year '2008' _journal_page_first '?' _journal_name_full 'The Journal of Organic Chemistry' _publ_contact_author_name 'Feihe Huang' _publ_contact_author_address ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; _publ_contact_author_email 'fhuang@zju.edu.cn' _publ_contact_author_fax '86-571-87953189' _publ_contact_author_phone '86-571-87953189' _publ_section_title ; Synthesis of cis- and trans-Dibenzo-30-Crown-10 Derivatives via Regioselective Routes and Their Complexations with Paraquat and Diquat ; loop_ _publ_author_name _publ_author_address 'Chunlin He' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; 'Zuming Shi' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; 'Qizhong Zhou' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; 'Shijun Li' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; 'Ning Li' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; 'Feihe Huang' ; Department of Chemistry Zhejiang University Hangzhou 310027, P. R. China ; data_1-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H58 F12 N2 O15 P2' _chemical_formula_weight 1120.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Cmc21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 20.757(7) _cell_length_b 10.663(2) _cell_length_c 22.319(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4940(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2328 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9329 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19011 _diffrn_reflns_av_R_equivalents 0.1099 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4268 _reflns_number_gt 1689 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(4) _refine_ls_number_reflns 4268 _refine_ls_number_parameters 367 _refine_ls_number_restraints 227 _refine_ls_R_factor_all 0.2549 _refine_ls_R_factor_gt 0.1309 _refine_ls_wR_factor_ref 0.3829 _refine_ls_wR_factor_gt 0.3018 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.104 _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 O1 O 0.5000 -0.1627(16) 0.7215(8) 0.146(6) Uani 1 2 d S . . O2 O 0.6184(5) -0.0368(12) 0.7390(6) 0.134(4) Uani 1 1 d D . . O3 O 0.6644(5) 0.1550(12) 0.8271(5) 0.116(3) Uani 1 1 d . A . O4 O 0.6683(4) 0.1837(10) 0.9407(4) 0.095(3) Uani 1 1 d . A . O5 O 0.6177(5) 0.0115(12) 1.0235(5) 0.126(4) Uani 1 1 d D . . O6 O 0.5000 -0.1021(16) 1.0516(7) 0.113(4) Uani 1 2 d S . . O7 O 0.6172(9) 0.7160(15) 0.8865(11) 0.225(8) Uani 1 1 d . A . H7 H 0.5805 0.6909 0.8930 0.338 Uiso 1 1 d R . . C11 C 0.5592(11) -0.175(2) 0.6885(11) 0.163(8) Uani 1 1 d U . . H11A H 0.5599 -0.2568 0.6698 0.196 Uiso 1 1 calc R A . H11B H 0.5591 -0.1129 0.6566 0.196 Uiso 1 1 calc R . . C12 C 0.6132(10) -0.1606(19) 0.7201(10) 0.141(6) Uani 1 1 d U A . H12A H 0.6501 -0.1826 0.6956 0.169 Uiso 1 1 calc R . . H12B H 0.6124 -0.2160 0.7546 0.169 Uiso 1 1 calc R . . C13 C 0.6822(12) -0.003(2) 0.765(2) 0.129(10) Uani 0.50 1 d PDU A 2 H13A H 0.7168 -0.0377 0.7410 0.155 Uiso 0.50 1 calc PR A 2 H13B H 0.6860 -0.0353 0.8055 0.155 Uiso 0.50 1 calc PR A 2 C13' C 0.6856(11) 0.006(2) 0.744(2) 0.129(10) Uani 0.50 1 d PDU A 1 H13C H 0.7069 0.0004 0.7054 0.155 Uiso 0.50 1 calc PR A 1 H13D H 0.7089 -0.0458 0.7724 0.155 Uiso 0.50 1 calc PR A 1 C14 C 0.6844(8) 0.1378(16) 0.7648(9) 0.131(5) Uani 1 1 d DU . . H14A H 0.7272 0.1731 0.7599 0.157 Uiso 1 1 calc R A 1 H14B H 0.6554 0.1850 0.7392 0.157 Uiso 1 1 calc R A 1 C15 C 0.6648(6) 0.2724(19) 0.8477(7) 0.100(4) Uani 1 1 d U . . C16 C 0.6623(6) 0.3762(18) 0.8129(7) 0.097(4) Uani 1 1 d U A . H16 H 0.6605 0.3620 0.7718 0.117 Uiso 1 1 calc R . . C17 C 0.6623(8) 0.492(2) 0.8291(8) 0.115(5) Uani 1 1 d U . . H17 H 0.6628 0.5580 0.8017 0.138 Uiso 1 1 calc R A . C18 C 0.6614(5) 0.5123(13) 0.8924(6) 0.086(4) Uani 1 1 d DU A . C19 C 0.6701(8) 0.4106(17) 0.9281(9) 0.137(6) Uani 1 1 d DU . . H19 H 0.6782 0.4228 0.9687 0.164 Uiso 1 1 calc R A . C20 C 0.6675(4) 0.2957(14) 0.9073(7) 0.079(3) Uani 1 1 d DU A . C21 C 0.6752(7) 0.1958(15) 1.0035(8) 0.123(5) Uani 1 1 d DU . . H21A H 0.6368 0.2297 1.0223 0.147 Uiso 1 1 calc R B 1 H21B H 0.7124 0.2460 1.0144 0.147 Uiso 1 1 calc R B 1 C22 C 0.6756(12) 0.086(2) 1.0428(11) 0.088(10) Uani 0.50 1 d PDU C 2 H22A H 0.6721 0.1105 1.0845 0.106 Uiso 0.50 1 calc PR C 2 H22B H 0.7148 0.0377 1.0375 0.106 Uiso 0.50 1 calc PR C 2 C22' C 0.6846(10) 0.060(2) 1.0173(14) 0.093(10) Uani 0.50 1 d PDU C 1 H22C H 0.7072 0.0179 0.9850 0.111 Uiso 0.50 1 calc PR C 1 H22D H 0.7087 0.0490 1.0542 0.111 Uiso 0.50 1 calc PR C 1 C23 C 0.6125(9) -0.096(2) 1.0558(9) 0.133(6) Uani 1 1 d U C . H23A H 0.6123 -0.0769 1.0982 0.160 Uiso 1 1 calc R . . H23B H 0.6493 -0.1498 1.0477 0.160 Uiso 1 1 calc R . . C24 C 0.5533(11) -0.1617(18) 1.0397(9) 0.143(6) Uani 1 1 d U . . H24A H 0.5543 -0.1796 0.9971 0.172 Uiso 1 1 calc R C . H24B H 0.5525 -0.2415 1.0606 0.172 Uiso 1 1 calc R . . C25 C 0.6603(9) 0.642(2) 0.9135(10) 0.138(6) Uani 1 1 d U . . H25A H 0.6513 0.6414 0.9562 0.166 Uiso 1 1 calc R A . H25B H 0.7028 0.6776 0.9080 0.166 Uiso 1 1 calc R . . N1 N 0.5000 0.1643(14) 0.8054(8) 0.092(5) Uani 1 2 d S . . N2 N 0.5000 0.1837(13) 0.9320(7) 0.094(4) Uani 1 2 d SD . . C1 C 0.5000 0.131(3) 0.7447(11) 0.120(7) Uani 1 2 d SU . . H1A H 0.5000 0.0485 0.7311 0.144 Uiso 1 2 calc SR . . C2 C 0.5000 0.229(3) 0.7092(12) 0.128(7) Uani 1 2 d SU . . H2 H 0.5000 0.2163 0.6680 0.153 Uiso 1 2 calc SR . . C3 C 0.5000 0.351(2) 0.7302(10) 0.097(6) Uani 1 2 d SU . . H3 H 0.5000 0.4189 0.7042 0.117 Uiso 1 2 calc SR . . C4 C 0.5000 0.367(2) 0.7927(12) 0.117(7) Uani 1 2 d SU . . H4 H 0.5000 0.4478 0.8081 0.141 Uiso 1 2 calc SR . . C5 C 0.5000 0.2691(15) 0.8314(6) 0.058(4) Uani 1 2 d SDU . . C6 C 0.5000 0.2914(15) 0.8909(7) 0.072(4) Uani 1 2 d SDU . . C7 C 0.5000 0.394(2) 0.9189(10) 0.114(6) Uani 1 2 d SDU . . H7A H 0.5000 0.4672 0.8965 0.137 Uiso 1 2 calc SR . . C8 C 0.5000 0.404(2) 0.9779(10) 0.114(7) Uani 1 2 d SDU . . H8A H 0.5000 0.4841 0.9947 0.137 Uiso 1 2 calc SR . . C9 C 0.5000 0.304(3) 1.0150(13) 0.133(7) Uani 1 2 d SDU . . H9 H 0.5000 0.3135 1.0564 0.159 Uiso 1 2 calc SR . . C10 C 0.5000 0.190(2) 0.9897(10) 0.106(6) Uani 1 2 d SDU . . H10 H 0.5000 0.1178 1.0130 0.128 Uiso 1 2 calc SR . . C100 C 0.5000 0.057(3) 0.8515(14) 0.166(11) Uani 1 2 d SDU . . H10A H 0.4628 0.0074 0.8404 0.199 Uiso 0.50 1 calc PR . . H10B H 0.5372 0.0074 0.8404 0.199 Uiso 0.50 1 calc PR . . C101 C 0.5000 0.053(2) 0.9158(15) 0.209(15) Uani 1 2 d SDU . . H10C H 0.5381 0.0108 0.9309 0.251 Uiso 0.50 1 calc PR . . H10D H 0.4619 0.0108 0.9309 0.251 Uiso 0.50 1 calc PR . . P1 P 0.64841(19) 0.4833(4) 0.6270(2) 0.1044(13) Uani 1 1 d . . . F1 F 0.6627(6) 0.4257(11) 0.5633(5) 0.174(4) Uani 1 1 d U . . F2 F 0.6359(6) 0.5326(10) 0.6891(5) 0.171(4) Uani 1 1 d U . . F3 F 0.6245(7) 0.3495(13) 0.6483(5) 0.182(5) Uani 1 1 d U . . F4 F 0.7109(7) 0.4272(17) 0.6510(7) 0.239(6) Uani 1 1 d U . . F5 F 0.6650(11) 0.6059(14) 0.6047(7) 0.243(7) Uani 1 1 d U . . F6 F 0.5800(10) 0.487(2) 0.6040(10) 0.278(8) Uani 1 1 d U . . O8 O 0.5000 0.681(2) 0.8313(11) 0.178(7) Uani 1 2 d S . . H8 H 0.5358 0.6942 0.8486 0.267 Uiso 1 1 d R . . O60 O 0.6500(18) 0.943(2) 0.9051(16) 0.343(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.154(15) 0.139(14) 0.144(14) -0.060(11) 0.000 0.000 O2 0.103(8) 0.137(10) 0.164(11) -0.022(8) -0.001(7) -0.004(7) O3 0.144(8) 0.117(9) 0.089(7) 0.019(6) 0.002(6) 0.006(6) O4 0.086(5) 0.126(8) 0.073(6) -0.003(5) -0.007(4) -0.004(5) O5 0.108(8) 0.146(9) 0.124(8) 0.039(7) -0.002(6) 0.036(7) O6 0.090(9) 0.131(12) 0.118(11) 0.031(9) 0.000 0.000 O7 0.198(15) 0.148(11) 0.33(2) -0.032(15) -0.079(16) 0.023(11) C11 0.151(14) 0.158(14) 0.181(15) -0.049(12) 0.003(13) 0.016(12) C12 0.140(13) 0.136(13) 0.147(13) -0.028(11) -0.017(11) 0.001(11) C13 0.105(11) 0.159(13) 0.123(18) -0.019(11) 0.020(10) 0.002(9) C13' 0.105(11) 0.159(13) 0.123(18) -0.019(11) 0.020(10) 0.002(9) C14 0.082(9) 0.153(12) 0.157(13) -0.005(11) -0.012(9) -0.009(8) C15 0.090(9) 0.111(11) 0.099(11) -0.002(10) 0.015(7) -0.017(8) C16 0.068(7) 0.124(11) 0.100(10) 0.006(9) 0.009(6) -0.001(8) C17 0.126(10) 0.122(12) 0.096(9) 0.009(9) -0.011(8) 0.010(10) C18 0.065(6) 0.082(8) 0.110(11) 0.006(8) -0.007(6) -0.016(6) C19 0.128(11) 0.135(13) 0.148(14) 0.006(12) -0.019(9) -0.017(10) C20 0.041(5) 0.088(9) 0.106(9) 0.003(8) -0.005(6) -0.004(5) C21 0.092(9) 0.155(13) 0.121(12) -0.002(10) 0.002(8) 0.009(9) C22 0.089(16) 0.099(16) 0.076(16) 0.010(13) 0.047(13) 0.003(13) C22' 0.085(16) 0.135(19) 0.058(14) -0.012(14) -0.006(12) 0.037(14) C23 0.116(11) 0.148(13) 0.136(12) 0.024(11) -0.001(9) 0.015(10) C24 0.168(14) 0.125(12) 0.138(12) 0.020(9) 0.010(12) 0.029(12) C25 0.125(11) 0.145(14) 0.145(12) 0.007(11) -0.016(10) 0.021(11) N1 0.088(10) 0.067(10) 0.123(14) 0.014(10) 0.000 0.000 N2 0.128(12) 0.064(10) 0.090(12) -0.001(8) 0.000 0.000 C1 0.126(14) 0.132(14) 0.102(13) 0.016(13) 0.000 0.000 C2 0.141(15) 0.118(14) 0.125(14) 0.006(13) 0.000 0.000 C3 0.049(8) 0.126(14) 0.116(13) 0.026(11) 0.000 0.000 C4 0.083(11) 0.126(15) 0.143(15) 0.003(13) 0.000 0.000 C5 0.052(8) 0.040(8) 0.082(9) -0.017(8) 0.000 0.000 C6 0.054(7) 0.061(9) 0.102(12) -0.016(9) 0.000 0.000 C7 0.122(13) 0.102(14) 0.118(14) 0.003(12) 0.000 0.000 C8 0.124(13) 0.101(13) 0.118(13) -0.022(12) 0.000 0.000 C9 0.130(14) 0.151(16) 0.117(14) -0.002(15) 0.000 0.000 C10 0.102(12) 0.112(14) 0.105(14) 0.011(11) 0.000 0.000 C100 0.209(19) 0.123(16) 0.167(18) 0.026(14) 0.000 0.000 C101 0.23(2) 0.20(2) 0.20(2) 0.000(18) 0.000 0.000 P1 0.106(3) 0.118(3) 0.090(3) 0.020(3) -0.004(2) 0.005(2) F1 0.251(11) 0.178(9) 0.093(6) -0.029(6) 0.019(6) -0.031(8) F2 0.284(12) 0.126(7) 0.105(7) 0.003(6) 0.006(7) 0.057(8) F3 0.217(11) 0.179(10) 0.149(8) -0.007(7) 0.043(7) -0.061(8) F4 0.171(10) 0.333(15) 0.213(11) -0.032(11) -0.044(8) 0.044(10) F5 0.404(18) 0.159(9) 0.167(10) 0.033(8) 0.007(10) -0.100(11) F6 0.235(13) 0.315(16) 0.283(16) -0.027(14) -0.052(12) 0.053(12) O8 0.121(12) 0.190(19) 0.22(2) -0.014(15) 0.000 0.000 O60 0.52(5) 0.183(19) 0.33(3) -0.01(2) -0.09(3) -0.04(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.44(2) 3_655 ? O1 C11 1.44(2) . ? O2 C12 1.39(2) . ? O2 C13' 1.471(19) . ? O2 C13 1.488(19) . ? O3 C15 1.333(19) . ? O3 C14 1.46(2) . ? O4 C20 1.409(15) . ? O4 C21 1.415(18) . ? O5 C23 1.36(2) . ? O5 C22' 1.489(18) . ? O5 C22 1.503(18) . ? O6 C24 1.30(2) . ? O6 C24 1.30(2) 3_655 ? O7 C25 1.339(19) . ? O7 H7 0.8199 . ? C11 C12 1.33(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.51(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13' C14 1.48(2) . ? C13' H13C 0.9700 . ? C13' H13D 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.354(17) . ? C15 C16 1.35(2) . ? C16 C17 1.29(2) . ? C16 H16 0.9300 . ? C17 C18 1.43(2) . ? C17 H17 0.9300 . ? C18 C19 1.359(15) . ? C18 C25 1.46(2) . ? C19 C20 1.311(15) . ? C19 H19 0.9300 . ? C21 C22 1.463(19) . ? C21 C22' 1.493(18) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22' H22C 0.9700 . ? C22' H22D 0.9700 . ? C23 C24 1.46(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? N1 C5 1.258(19) . ? N1 C1 1.40(3) . ? N1 C100 1.54(3) . ? N2 C10 1.29(2) . ? N2 C101 1.440(19) . ? N2 C6 1.47(2) . ? C1 C2 1.31(3) . ? C1 H1A 0.9300 . ? C2 C3 1.38(3) . ? C2 H2 0.9300 . ? C3 C4 1.41(3) . ? C3 H3 0.9300 . ? C4 C5 1.35(3) . ? C4 H4 0.9300 . ? C5 C6 1.350(15) . ? C6 C7 1.258(16) . ? C7 C8 1.323(17) . ? C7 H7A 0.9300 . ? C8 C9 1.35(3) . ? C8 H8A 0.9300 . ? C9 C10 1.338(18) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C100 C101 1.435(19) . ? C100 H10A 0.9700 . ? C100 H10B 0.9700 . ? C101 H10C 0.9700 . ? C101 H10D 0.9700 . ? P1 F5 1.441(14) . ? P1 F2 1.504(11) . ? P1 F6 1.512(19) . ? P1 F4 1.525(15) . ? P1 F1 1.579(11) . ? P1 F3 1.584(14) . ? O8 H8 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C11 117(2) 3_655 . ? C12 O2 C13' 113.1(15) . . ? C12 O2 C13 114.6(15) . . ? C13' O2 C13 19(3) . . ? C15 O3 C14 116.4(12) . . ? C20 O4 C21 116.7(12) . . ? C23 O5 C22' 114.6(13) . . ? C23 O5 C22 111.0(13) . . ? C22' O5 C22 25.4(13) . . ? C24 O6 C24 116(2) . 3_655 ? C25 O7 H7 110.3 . . ? C12 C11 O1 115.9(19) . . ? C12 C11 H11A 108.3 . . ? O1 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? O1 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C11 C12 O2 109.5(17) . . ? C11 C12 H12A 109.8 . . ? O2 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? O2 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? O2 C13 C14 105.4(17) . . ? O2 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? O2 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? O2 C13' C14 107.7(18) . . ? O2 C13' H13C 110.2 . . ? C14 C13' H13C 110.2 . . ? O2 C13' H13D 110.2 . . ? C14 C13' H13D 110.2 . . ? H13C C13' H13D 108.5 . . ? O3 C14 C13' 115(2) . . ? O3 C14 C13 96(2) . . ? C13' C14 C13 19(3) . . ? O3 C14 H14A 108.5 . . ? C13' C14 H14A 108.5 . . ? C13 C14 H14A 114.6 . . ? O3 C14 H14B 108.5 . . ? C13' C14 H14B 108.5 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 107.5 . . ? O3 C15 C20 120.8(16) . . ? O3 C15 C16 124.7(15) . . ? C20 C15 C16 114.5(16) . . ? C17 C16 C15 128.5(17) . . ? C17 C16 H16 115.7 . . ? C15 C16 H16 115.7 . . ? C16 C17 C18 115.0(16) . . ? C16 C17 H17 122.5 . . ? C18 C17 H17 122.5 . . ? C19 C18 C17 117.3(15) . . ? C19 C18 C25 124.6(15) . . ? C17 C18 C25 117.5(15) . . ? C20 C19 C18 122.2(17) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C15 121.4(16) . . ? C19 C20 O4 127.1(15) . . ? C15 C20 O4 111.4(14) . . ? O4 C21 C22 121.3(17) . . ? O4 C21 C22' 97.4(17) . . ? C22 C21 C22' 25.7(13) . . ? O4 C21 H21A 112.3 . . ? C22 C21 H21A 92.5 . . ? C22' C21 H21A 112.3 . . ? O4 C21 H21B 112.3 . . ? C22 C21 H21B 106.7 . . ? C22' C21 H21B 112.3 . . ? H21A C21 H21B 109.9 . . ? C21 C22 O5 104.3(16) . . ? C21 C22 H22A 110.9 . . ? O5 C22 H22A 110.9 . . ? C21 C22 H22B 110.9 . . ? O5 C22 H22B 110.9 . . ? H22A C22 H22B 108.9 . . ? O5 C22' C21 103.5(15) . . ? O5 C22' H22C 111.1 . . ? C21 C22' H22C 111.1 . . ? O5 C22' H22D 111.1 . . ? C21 C22' H22D 111.1 . . ? H22C C22' H22D 109.0 . . ? O5 C23 C24 109.9(16) . . ? O5 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? O5 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? O6 C24 C23 115.6(17) . . ? O6 C24 H24A 108.4 . . ? C23 C24 H24A 108.4 . . ? O6 C24 H24B 108.4 . . ? C23 C24 H24B 108.4 . . ? H24A C24 H24B 107.4 . . ? O7 C25 C18 115.1(16) . . ? O7 C25 H25A 108.5 . . ? C18 C25 H25A 108.5 . . ? O7 C25 H25B 108.5 . . ? C18 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C5 N1 C1 132.1(19) . . ? C5 N1 C100 111(2) . . ? C1 N1 C100 117(2) . . ? C10 N2 C101 108(2) . . ? C10 N2 C6 125.7(16) . . ? C101 N2 C6 126.8(19) . . ? C2 C1 N1 112(2) . . ? C2 C1 H1A 123.8 . . ? N1 C1 H1A 123.8 . . ? C1 C2 C3 123(3) . . ? C1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C2 C3 C4 117(2) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? C5 C4 C3 123(2) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? N1 C5 C6 127.5(17) . . ? N1 C5 C4 113.0(18) . . ? C6 C5 C4 119.5(17) . . ? C7 C6 C5 129.9(18) . . ? C7 C6 N2 111.6(17) . . ? C5 C6 N2 118.5(14) . . ? C6 C7 C8 125(2) . . ? C6 C7 H7A 117.7 . . ? C8 C7 H7A 117.7 . . ? C7 C8 C9 123(2) . . ? C7 C8 H8A 118.6 . . ? C9 C8 H8A 118.6 . . ? C10 C9 C8 117(3) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? N2 C10 C9 118(2) . . ? N2 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C101 C100 N1 134(3) . . ? C101 C100 H10A 103.7 . . ? N1 C100 H10A 103.7 . . ? C101 C100 H10B 103.7 . . ? N1 C100 H10B 103.7 . . ? H10A C100 H10B 105.4 . . ? C100 C101 N2 103(3) . . ? C100 C101 H10C 111.2 . . ? N2 C101 H10C 111.2 . . ? C100 C101 H10D 111.2 . . ? N2 C101 H10D 111.2 . . ? H10C C101 H10D 109.1 . . ? F5 P1 F2 92.5(8) . . ? F5 P1 F6 94.7(13) . . ? F2 P1 F6 98.2(10) . . ? F5 P1 F4 105.9(12) . . ? F2 P1 F4 87.7(8) . . ? F6 P1 F4 158.3(12) . . ? F5 P1 F1 89.8(9) . . ? F2 P1 F1 177.3(7) . . ? F6 P1 F1 83.1(9) . . ? F4 P1 F1 90.2(8) . . ? F5 P1 F3 174.9(10) . . ? F2 P1 F3 89.1(6) . . ? F6 P1 F3 80.3(11) . . ? F4 P1 F3 78.9(9) . . ? F1 P1 F3 88.8(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.555 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.105 #===END data_2-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H56 F12 N2 O12 P2' _chemical_formula_weight 1070.83 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.3885(13) _cell_length_b 18.885(2) _cell_length_c 22.602(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4861.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3602 _cell_measurement_theta_min 4.549 _cell_measurement_theta_max 39.641 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.503 _exptl_crystal_size_mid 0.482 _exptl_crystal_size_min 0.371 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75081 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26463 _diffrn_reflns_av_R_equivalents 0.1208 _diffrn_reflns_av_sigmaI/netI 0.1258 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9457 _reflns_number_gt 4452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1020P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(17) _chemical_absolute_configuration ad _refine_ls_number_reflns 9457 _refine_ls_number_parameters 636 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.881 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.003 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 P1 P -0.2525(2) 0.18739(10) 1.01149(8) 0.0840(6) Uani 1 1 d . . . P2 P 0.87482(16) 0.17778(8) 0.50545(6) 0.0624(4) Uani 1 1 d . . . O1 O 0.4377(4) 0.1520(2) 0.80500(15) 0.0645(11) Uani 1 1 d . . . O2 O 0.3781(4) 0.0362(2) 0.87903(19) 0.0778(12) Uani 1 1 d . . . O3 O 0.2251(5) -0.0852(2) 0.8888(3) 0.0980(16) Uani 1 1 d . . . O4 O -0.0133(4) -0.0566(2) 0.90797(19) 0.0814(13) Uani 1 1 d . . . O5 O -0.1417(3) 0.01877(19) 0.81855(14) 0.0584(10) Uani 1 1 d . . . O6 O -0.1013(4) 0.0390(2) 0.70757(16) 0.0685(11) Uani 1 1 d . . . O7 O 0.0673(5) -0.0399(2) 0.6455(2) 0.0985(16) Uani 1 1 d . . . O8 O 0.2957(6) -0.0773(3) 0.6137(3) 0.119(3) Uani 1 1 d . . . O9 O 0.4753(4) 0.0204(3) 0.6149(3) 0.1072(17) Uani 1 1 d . . . O10 O 0.4938(3) 0.1413(2) 0.69443(16) 0.0622(10) Uani 1 1 d . . . O11 O 0.1510(5) 0.3784(3) 0.7601(2) 0.0969(15) Uani 1 1 d D . . O12 O -0.1416(6) 0.3228(3) 0.7125(3) 0.113(2) Uani 1 1 d . . . H12 H -0.1409 0.3468 0.6822 0.145 Uiso 1 1 calc R . . N1 N 0.1243(4) 0.0894(2) 0.81192(17) 0.0472(10) Uani 1 1 d . . . N2 N 0.2107(4) 0.0997(2) 0.69636(17) 0.0471(10) Uani 1 1 d . . . F1 F -0.2232(15) 0.2115(4) 0.9505(3) 0.208(7) Uani 1 1 d . . . F2 F -0.2607(6) 0.2671(2) 1.0299(2) 0.1354(19) Uani 1 1 d . . . F3 F -0.2691(8) 0.1660(3) 1.0736(2) 0.203(3) Uani 1 1 d . . . F4 F -0.2442(10) 0.1099(3) 0.9921(3) 0.223(4) Uani 1 1 d . . . F5 F -0.1274(7) 0.1841(5) 1.0195(7) 0.239(8) Uani 1 1 d . . . F6 F -0.3762(8) 0.1885(6) 1.0031(7) 0.266(9) Uani 1 1 d . . . F7 F 0.8787(5) 0.2106(2) 0.57019(14) 0.1117(15) Uani 1 1 d . . . F8 F 0.7678(6) 0.2224(3) 0.4886(3) 0.180(3) Uani 1 1 d . . . F9 F 0.9839(4) 0.1303(3) 0.5231(2) 0.1378(19) Uani 1 1 d . . . F10 F 0.8754(4) 0.1437(2) 0.44169(14) 0.1011(13) Uani 1 1 d . . . F11 F 0.7908(4) 0.1179(3) 0.52918(16) 0.1183(16) Uani 1 1 d . . . F12 F 0.9543(7) 0.2388(3) 0.4829(2) 0.186(3) Uani 1 1 d . . . C1 C 0.4513(4) 0.2044(3) 0.7106(2) 0.0504(13) Uani 1 1 d . . . C2 C 0.4354(5) 0.2610(3) 0.6746(2) 0.0637(16) Uani 1 1 d . . . H2 H 0.4592 0.2585 0.6353 0.076 Uiso 1 1 calc R . . C3 C 0.3833(6) 0.3237(3) 0.6960(3) 0.0715(17) Uani 1 1 d . . . H3 H 0.3753 0.3624 0.6709 0.086 Uiso 1 1 calc R . . C4 C 0.3450(6) 0.3286(3) 0.7524(3) 0.0673(17) Uani 1 1 d . . . C5 C 0.3658(5) 0.2727(3) 0.7908(2) 0.0616(15) Uani 1 1 d . . . H5 H 0.3452 0.2770 0.8304 0.074 Uiso 1 1 calc R . . C6 C 0.4166(5) 0.2108(3) 0.7711(2) 0.0529(14) Uani 1 1 d . . . C7 C 0.4157(6) 0.1593(3) 0.8671(2) 0.0657(16) Uani 1 1 d . . . H7A H 0.3328 0.1677 0.8740 0.079 Uiso 1 1 calc R . . H7B H 0.4596 0.1991 0.8828 0.079 Uiso 1 1 calc R . . C8 C 0.4528(6) 0.0928(3) 0.8967(3) 0.0789(19) Uani 1 1 d . . . H8A H 0.5333 0.0820 0.8861 0.095 Uiso 1 1 calc R . . H8B H 0.4489 0.0987 0.9393 0.095 Uiso 1 1 calc R . . C9 C 0.4092(7) -0.0253(4) 0.9117(4) 0.119(3) Uani 1 1 d D . . H9A H 0.4933 -0.0328 0.9094 0.132 Uiso 1 1 calc R . . H9B H 0.3882 -0.0190 0.9530 0.132 Uiso 1 1 calc R . . C10 C 0.3499(8) -0.0846(4) 0.8885(6) 0.118(5) Uani 1 1 d D . . H10A H 0.3764 -0.1259 0.9102 0.142 Uiso 1 1 calc R . . H10B H 0.3754 -0.0905 0.8478 0.142 Uiso 1 1 calc R . . C11 C 0.1692(9) -0.1024(5) 0.9422(4) 0.114(3) Uani 1 1 d . . . H11A H 0.1758 -0.0632 0.9697 0.137 Uiso 1 1 calc R . . H11B H 0.2066 -0.1435 0.9598 0.137 Uiso 1 1 calc R . . C12 C 0.0439(9) -0.1178(4) 0.9304(3) 0.108(3) Uani 1 1 d . . . H12A H 0.0378 -0.1560 0.9018 0.130 Uiso 1 1 calc R . . H12B H 0.0059 -0.1328 0.9666 0.130 Uiso 1 1 calc R . . C13 C -0.1317(7) -0.0669(4) 0.8943(3) 0.086(2) Uani 1 1 d . . . H13A H -0.1732 -0.0848 0.9287 0.103 Uiso 1 1 calc R . . H13B H -0.1393 -0.1012 0.8626 0.103 Uiso 1 1 calc R . . C14 C -0.1818(6) 0.0009(4) 0.8760(3) 0.0765(19) Uani 1 1 d . . . H14A H -0.2668 -0.0022 0.8760 0.092 Uiso 1 1 calc R . . H14B H -0.1589 0.0375 0.9038 0.092 Uiso 1 1 calc R . . C15 C -0.1737(5) 0.0840(4) 0.7970(2) 0.0597(15) Uani 1 1 d . . . C16 C -0.2274(5) 0.1364(4) 0.8278(3) 0.0687(16) Uani 1 1 d . . . H16 H -0.2494 0.1278 0.8668 0.082 Uiso 1 1 calc R . . C17 C -0.2505(6) 0.2018(4) 0.8035(3) 0.0803(19) Uani 1 1 d . . . H17 H -0.2844 0.2374 0.8263 0.096 Uiso 1 1 calc R . . C18 C -0.2234(6) 0.2135(3) 0.7464(3) 0.0722(18) Uani 1 1 d . . . C19 C -0.1723(5) 0.1611(4) 0.7116(3) 0.0700(18) Uani 1 1 d . . . H19 H -0.1542 0.1696 0.6721 0.084 Uiso 1 1 calc R . . C20 C -0.1491(5) 0.0955(3) 0.7376(2) 0.0546(14) Uani 1 1 d . . . C21 C -0.0827(5) 0.0476(3) 0.6456(2) 0.0627(16) Uani 1 1 d . . . H21A H -0.0235 0.0836 0.6387 0.075 Uiso 1 1 calc R . . H21B H -0.1550 0.0626 0.6267 0.075 Uiso 1 1 calc R . . C22 C -0.0432(6) -0.0214(4) 0.6201(3) 0.0726(18) Uani 1 1 d . . . H22A H -0.1006 -0.0580 0.6288 0.087 Uiso 1 1 calc R . . H22B H -0.0358 -0.0174 0.5775 0.087 Uiso 1 1 calc R . . C23 C 0.1016(11) -0.1093(5) 0.6333(6) 0.117(4) Uani 1 1 d D . . H23A H 0.0356 -0.1353 0.6171 0.138 Uiso 1 1 calc R . . H23B H 0.1254 -0.1323 0.6698 0.138 Uiso 1 1 calc R . . C24 C 0.1947(13) -0.1105(5) 0.5930(5) 0.127(5) Uani 1 1 d D . . H24A H 0.2132 -0.1594 0.5836 0.140 Uiso 1 1 calc R . . H24B H 0.1700 -0.0875 0.5567 0.140 Uiso 1 1 calc R . . C25 C 0.3911(12) -0.0883(5) 0.5850(6) 0.128(7) Uani 1 1 d . . . H25A H 0.3740 -0.0802 0.5435 0.137 Uiso 1 1 calc R . . H25B H 0.4098 -0.1382 0.5891 0.137 Uiso 1 1 calc R . . C26 C 0.4945(8) -0.0498(5) 0.5985(5) 0.129(4) Uani 1 1 d . . . H26A H 0.5352 -0.0737 0.6305 0.137 Uiso 1 1 calc R . . H26B H 0.5456 -0.0505 0.5642 0.137 Uiso 1 1 calc R . . C27 C 0.5762(6) 0.0606(4) 0.6248(3) 0.086(2) Uani 1 1 d . . . H27A H 0.6280 0.0573 0.5909 0.103 Uiso 1 1 calc R . . H27B H 0.6177 0.0427 0.6591 0.103 Uiso 1 1 calc R . . C28 C 0.5416(6) 0.1370(3) 0.6349(3) 0.0709(17) Uani 1 1 d . . . H28A H 0.6095 0.1676 0.6311 0.085 Uiso 1 1 calc R . . H28B H 0.4831 0.1515 0.6062 0.085 Uiso 1 1 calc R . . C29 C 0.2710(7) 0.3919(3) 0.7737(3) 0.0822(19) Uani 1 1 d . . . H29A H 0.2804 0.3982 0.8160 0.099 Uiso 1 1 calc R . . H29B H 0.2967 0.4349 0.7541 0.099 Uiso 1 1 calc R . . C30 C -0.2515(8) 0.2842(4) 0.7162(4) 0.105(3) Uani 1 1 d . . . H30A H -0.2834 0.2762 0.6770 0.126 Uiso 1 1 calc R . . H30B H -0.3084 0.3107 0.7392 0.126 Uiso 1 1 calc R . . C31 C 0.0961(5) 0.0829(3) 0.8695(2) 0.0592(15) Uani 1 1 d . . . H31 H 0.1008 0.0391 0.8882 0.071 Uiso 1 1 calc R . . C32 C 0.0605(6) 0.1413(4) 0.9001(2) 0.0687(17) Uani 1 1 d . . . H32 H 0.0426 0.1372 0.9401 0.082 Uiso 1 1 calc R . . C33 C 0.0508(5) 0.2053(3) 0.8733(3) 0.0680(17) Uani 1 1 d . . . H33 H 0.0220 0.2442 0.8938 0.082 Uiso 1 1 calc R . . C34 C 0.0845(5) 0.2115(3) 0.8146(2) 0.0515(13) Uani 1 1 d . . . H34 H 0.0840 0.2556 0.7962 0.062 Uiso 1 1 calc R . . C35 C 0.1186(4) 0.1527(3) 0.7835(2) 0.0438(12) Uani 1 1 d . . . C36 C 0.1506(4) 0.1544(3) 0.72034(19) 0.0390(11) Uani 1 1 d . . . C37 C 0.1188(5) 0.2103(3) 0.6843(2) 0.0505(13) Uani 1 1 d . . . H37 H 0.0761 0.2482 0.6995 0.061 Uiso 1 1 calc R . . C38 C 0.1512(5) 0.2093(3) 0.6252(2) 0.0587(15) Uani 1 1 d . . . H38 H 0.1310 0.2472 0.6009 0.070 Uiso 1 1 calc R . . C39 C 0.2118(5) 0.1541(3) 0.6021(2) 0.0606(15) Uani 1 1 d . . . H39 H 0.2328 0.1537 0.5623 0.073 Uiso 1 1 calc R . . C40 C 0.2416(5) 0.0990(3) 0.6384(2) 0.0607(15) Uani 1 1 d . . . H40 H 0.2832 0.0607 0.6232 0.073 Uiso 1 1 calc R . . C41 C 0.2505(5) 0.0421(3) 0.7356(2) 0.0590(15) Uani 1 1 d . . . H41A H 0.3202 0.0568 0.7570 0.071 Uiso 1 1 calc R . . H41B H 0.2701 0.0006 0.7123 0.071 Uiso 1 1 calc R . . C42 C 0.1553(5) 0.0246(2) 0.7781(2) 0.0566(15) Uani 1 1 d . . . H42A H 0.1814 -0.0122 0.8050 0.068 Uiso 1 1 calc R . . H42B H 0.0870 0.0073 0.7569 0.068 Uiso 1 1 calc R . . H11 H 0.075(2) 0.375(3) 0.748(3) 0.08(2) Uiso 1 1 d 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 P1 0.1103(17) 0.0844(13) 0.0572(10) -0.0110(9) 0.0065(10) 0.0236(11) P2 0.0887(12) 0.0570(9) 0.0414(8) 0.0036(7) -0.0105(8) -0.0067(9) O1 0.088(3) 0.054(2) 0.051(2) 0.0042(18) 0.0009(19) 0.001(2) O2 0.078(3) 0.058(3) 0.098(3) 0.027(2) -0.006(3) 0.008(2) O3 0.096(4) 0.071(3) 0.127(5) 0.026(3) -0.036(3) -0.009(3) O4 0.084(3) 0.071(3) 0.090(3) 0.026(2) -0.013(3) -0.016(2) O5 0.074(3) 0.058(2) 0.043(2) 0.0055(17) 0.0070(19) 0.000(2) O6 0.080(3) 0.076(3) 0.049(2) 0.0080(19) 0.002(2) -0.002(2) O7 0.100(4) 0.054(3) 0.142(5) -0.021(3) -0.020(3) 0.000(2) O8 0.098(5) 0.117(5) 0.203(8) -0.100(5) 0.002(5) 0.019(4) O9 0.086(4) 0.079(3) 0.157(5) -0.051(3) 0.023(3) 0.009(3) O10 0.072(3) 0.056(2) 0.059(2) -0.0009(18) 0.0096(19) 0.011(2) O11 0.097(5) 0.081(3) 0.113(4) -0.013(3) -0.007(3) 0.011(3) O12 0.154(6) 0.095(5) 0.181(7) 0.029(4) -0.024(5) -0.034(4) N1 0.051(3) 0.041(2) 0.050(3) 0.0028(19) -0.002(2) -0.006(2) N2 0.048(3) 0.048(3) 0.045(2) -0.004(2) -0.006(2) 0.000(2) F1 0.40(2) 0.136(5) 0.091(4) 0.021(3) 0.117(7) 0.103(10) F2 0.192(5) 0.091(3) 0.123(4) -0.025(3) 0.039(3) 0.010(3) F3 0.302(10) 0.157(5) 0.099(4) 0.011(3) 0.061(5) -0.008(6) F4 0.323(12) 0.086(3) 0.161(5) -0.034(3) 0.082(7) 0.036(6) F5 0.111(6) 0.225(10) 0.68(2) 0.057(12) 0.092(9) 0.025(6) F6 0.184(8) 0.307(12) 0.61(2) -0.153(14) -0.263(12) 0.073(9) F7 0.194(5) 0.092(3) 0.049(2) -0.0120(17) -0.006(3) 0.003(3) F8 0.194(6) 0.202(6) 0.145(4) 0.009(4) -0.066(4) 0.114(5) F9 0.118(4) 0.183(5) 0.112(4) -0.014(3) -0.034(3) 0.048(4) F10 0.150(4) 0.097(3) 0.055(2) -0.0149(18) -0.007(2) -0.034(3) F11 0.140(4) 0.137(4) 0.077(3) 0.023(2) -0.005(2) -0.058(3) F12 0.301(9) 0.157(5) 0.080(3) 0.001(3) 0.011(4) -0.161(5) C1 0.042(3) 0.055(4) 0.055(3) 0.004(3) 0.000(2) -0.008(3) C2 0.067(4) 0.071(4) 0.052(3) 0.003(3) 0.007(3) -0.008(3) C3 0.098(5) 0.053(4) 0.063(4) -0.003(3) -0.001(3) -0.002(4) C4 0.088(5) 0.050(4) 0.064(4) -0.007(3) -0.007(3) 0.007(3) C5 0.072(4) 0.064(4) 0.048(3) 0.000(3) -0.003(3) 0.001(3) C6 0.057(4) 0.040(3) 0.061(3) 0.004(3) -0.007(3) 0.000(3) C7 0.077(4) 0.068(4) 0.053(3) 0.007(3) -0.005(3) -0.016(3) C8 0.089(5) 0.077(5) 0.071(4) 0.020(3) -0.021(4) -0.015(4) C9 0.100(6) 0.084(6) 0.172(8) 0.054(6) -0.051(6) -0.006(5) C10 0.090(7) 0.074(6) 0.240(16) 0.043(7) -0.103(8) -0.001(5) C11 0.150(9) 0.099(6) 0.093(6) 0.004(5) -0.061(6) 0.026(6) C12 0.163(9) 0.075(5) 0.087(5) 0.050(4) 0.004(5) -0.002(5) C13 0.103(6) 0.088(5) 0.065(4) 0.030(3) 0.006(4) -0.020(4) C14 0.073(4) 0.088(5) 0.069(4) 0.015(4) 0.023(3) -0.011(4) C15 0.042(3) 0.085(5) 0.052(3) -0.005(3) -0.001(3) -0.005(3) C16 0.067(4) 0.083(5) 0.057(4) -0.004(3) 0.004(3) -0.004(4) C17 0.080(5) 0.081(5) 0.080(5) -0.004(4) -0.010(4) -0.002(4) C18 0.071(5) 0.064(4) 0.081(5) 0.006(4) -0.021(4) 0.006(3) C19 0.048(3) 0.090(5) 0.072(4) 0.014(4) -0.013(3) -0.005(3) C20 0.040(3) 0.061(4) 0.063(4) 0.008(3) -0.010(3) -0.012(3) C21 0.048(4) 0.099(5) 0.042(3) 0.016(3) 0.000(2) -0.008(3) C22 0.078(5) 0.092(5) 0.048(3) -0.003(3) -0.011(3) -0.020(4) C23 0.191(12) 0.072(6) 0.207(12) -0.048(7) -0.032(10) 0.015(7) C24 0.197(14) 0.082(7) 0.200(12) -0.093(7) 0.011(11) -0.019(8) C25 0.163(11) 0.104(8) 0.226(17) -0.118(10) 0.105(12) -0.012(8) C26 0.097(7) 0.096(7) 0.205(12) -0.070(7) 0.002(7) 0.043(6) C27 0.058(4) 0.110(6) 0.090(5) -0.025(4) 0.016(4) 0.000(4) C28 0.059(4) 0.083(5) 0.071(4) -0.010(3) 0.011(3) 0.004(3) C29 0.090(6) 0.065(4) 0.091(5) -0.018(3) 0.000(4) 0.000(4) C30 0.111(7) 0.082(5) 0.123(6) 0.034(4) -0.026(5) -0.002(5) C31 0.059(4) 0.068(4) 0.052(3) 0.007(3) -0.004(3) -0.012(3) C32 0.083(4) 0.077(5) 0.046(3) -0.007(3) 0.005(3) -0.008(3) C33 0.074(4) 0.068(4) 0.062(4) -0.013(3) 0.007(3) 0.006(3) C34 0.052(3) 0.048(3) 0.054(3) -0.005(2) 0.005(3) 0.004(3) C35 0.042(3) 0.040(3) 0.050(3) 0.000(2) -0.005(2) -0.002(2) C36 0.036(3) 0.039(3) 0.042(3) -0.002(2) 0.000(2) 0.002(2) C37 0.054(3) 0.045(3) 0.052(3) 0.001(2) 0.008(3) 0.008(3) C38 0.069(4) 0.059(4) 0.048(3) 0.015(3) -0.005(3) -0.008(3) C39 0.057(4) 0.074(4) 0.051(3) -0.001(3) 0.001(3) -0.007(3) C40 0.053(4) 0.065(4) 0.065(4) -0.013(3) 0.010(3) 0.000(3) C41 0.059(4) 0.049(3) 0.068(4) 0.002(3) -0.020(3) 0.005(3) C42 0.081(4) 0.030(3) 0.060(3) 0.003(2) -0.012(3) 0.000(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 P1 F6 1.421(8) . ? P1 F5 1.437(8) . ? P1 F3 1.473(5) . ? P1 F1 1.489(6) . ? P1 F4 1.530(5) . ? P1 F2 1.565(5) . ? P2 F8 1.529(5) . ? P2 F12 1.551(5) . ? P2 F11 1.576(4) . ? P2 F10 1.578(3) . ? P2 F9 1.583(5) . ? P2 F7 1.590(4) . ? O1 C6 1.372(6) . ? O1 C7 1.433(6) . ? O2 C9 1.420(7) . ? O2 C8 1.424(7) . ? O3 C11 1.403(10) . ? O3 C10 1.422(9) . ? O4 C13 1.397(8) . ? O4 C12 1.419(8) . ? O5 C15 1.374(7) . ? O5 C14 1.417(6) . ? O6 C20 1.377(7) . ? O6 C21 1.426(6) . ? O7 C23 1.395(9) . ? O7 C22 1.426(7) . ? O8 C25 1.283(11) . ? O8 C24 1.391(12) . ? O9 C26 1.395(8) . ? O9 C27 1.396(8) . ? O10 C1 1.338(6) . ? O10 C28 1.453(6) . ? O11 C29 1.424(9) . ? O11 H11 0.91(2) . ? O12 C30 1.450(9) . ? O12 H12 0.8200 . ? N1 C31 1.346(6) . ? N1 C35 1.359(6) . ? N1 C42 1.486(6) . ? N2 C36 1.353(6) . ? N2 C40 1.357(6) . ? N2 C41 1.475(6) . ? F1 H32 3.3448 . ? F11 H27A 2.5858 . ? C1 C2 1.356(7) . ? C1 C6 1.427(7) . ? C2 C3 1.409(8) . ? C2 H2 0.9300 . ? C3 C4 1.350(8) . ? C3 H3 0.9300 . ? C4 C5 1.387(7) . ? C4 C29 1.541(8) . ? C5 C6 1.377(7) . ? C5 H5 0.9300 . ? C7 C8 1.484(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.409(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.481(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.461(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.356(8) . ? C15 C20 1.387(7) . ? C16 C17 1.378(8) . ? C16 H16 0.9300 . ? C17 C18 1.345(9) . ? C17 H17 0.9300 . ? C18 C19 1.391(9) . ? C18 C30 1.534(9) . ? C19 C20 1.397(8) . ? C19 H19 0.9300 . ? C21 C22 1.495(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.399(12) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.417(13) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.513(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.363(8) . ? C31 H31 0.9300 . ? C32 C33 1.356(8) . ? C32 H32 0.9300 . ? C33 C34 1.386(7) . ? C33 H33 0.9300 . ? C34 C35 1.369(7) . ? C34 H34 0.9300 . ? C35 C36 1.474(6) . ? C36 C37 1.382(7) . ? C37 C38 1.386(7) . ? C37 H37 0.9300 . ? C38 C39 1.355(8) . ? C38 H38 0.9300 . ? C39 C40 1.367(8) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C42 1.485(8) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? 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 F6 P1 F5 178.3(6) . . ? F6 P1 F3 90.2(8) . . ? F5 P1 F3 89.7(7) . . ? F6 P1 F1 95.4(8) . . ? F5 P1 F1 84.7(8) . . ? F3 P1 F1 174.0(8) . . ? F6 P1 F4 92.1(6) . . ? F5 P1 F4 86.2(6) . . ? F3 P1 F4 91.1(4) . . ? F1 P1 F4 90.8(4) . . ? F6 P1 F2 87.9(5) . . ? F5 P1 F2 93.8(6) . . ? F3 P1 F2 90.1(3) . . ? F1 P1 F2 88.0(3) . . ? F4 P1 F2 178.8(3) . . ? F8 P2 F12 88.5(4) . . ? F8 P2 F11 89.8(4) . . ? F12 P2 F11 177.9(4) . . ? F8 P2 F10 90.1(3) . . ? F12 P2 F10 90.1(2) . . ? F11 P2 F10 91.2(2) . . ? F8 P2 F9 178.9(4) . . ? F12 P2 F9 92.6(4) . . ? F11 P2 F9 89.1(3) . . ? F10 P2 F9 89.8(3) . . ? F8 P2 F7 92.1(3) . . ? F12 P2 F7 89.7(3) . . ? F11 P2 F7 89.1(2) . . ? F10 P2 F7 177.8(3) . . ? F9 P2 F7 88.1(2) . . ? C6 O1 C7 116.0(4) . . ? C9 O2 C8 108.6(5) . . ? C11 O3 C10 117.3(7) . . ? C13 O4 C12 114.2(6) . . ? C15 O5 C14 117.0(4) . . ? C20 O6 C21 117.0(4) . . ? C23 O7 C22 113.4(6) . . ? C25 O8 C24 117.2(9) . . ? C26 O9 C27 115.5(6) . . ? C1 O10 C28 116.1(4) . . ? C29 O11 H11 172(4) . . ? C30 O12 H12 109.5 . . ? C31 N1 C35 121.7(4) . . ? C31 N1 C42 118.7(4) . . ? C35 N1 C42 119.5(4) . . ? C36 N2 C40 121.7(4) . . ? C36 N2 C41 118.6(4) . . ? C40 N2 C41 119.6(5) . . ? P1 F1 H32 98.0 . . ? P2 F11 H27A 159.4 . . ? O10 C1 C2 125.9(5) . . ? O10 C1 C6 115.9(5) . . ? C2 C1 C6 118.1(5) . . ? C1 C2 C3 120.8(5) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 121.2(6) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 C29 121.7(6) . . ? C5 C4 C29 119.3(6) . . ? C6 C5 C4 121.0(5) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? O1 C6 C5 125.4(5) . . ? O1 C6 C1 114.7(5) . . ? C5 C6 C1 119.8(5) . . ? O1 C7 C8 108.0(5) . . ? O1 C7 H7A 110.1 . . ? C8 C7 H7A 110.1 . . ? O1 C7 H7B 110.1 . . ? C8 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? O2 C8 C7 109.9(5) . . ? O2 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? O2 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 O2 109.6(6) . . ? C10 C9 H9A 109.7 . . ? O2 C9 H9A 109.7 . . ? C10 C9 H9B 109.8 . . ? O2 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 O3 118.9(8) . . ? C9 C10 H10A 107.6 . . ? O3 C10 H10A 107.6 . . ? C9 C10 H10B 107.6 . . ? O3 C10 H10B 107.6 . . ? H10A C10 H10B 107.0 . . ? O3 C11 C12 109.1(6) . . ? O3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O4 C12 C11 110.3(6) . . ? O4 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? O4 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O4 C13 C14 108.5(6) . . ? O4 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? O4 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? O5 C14 C13 110.0(5) . . ? O5 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? O5 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 O5 126.2(5) . . ? C16 C15 C20 118.3(6) . . ? O5 C15 C20 115.5(5) . . ? C15 C16 C17 122.4(6) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C18 C17 C16 119.0(6) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C17 C18 C19 121.5(6) . . ? C17 C18 C30 121.5(7) . . ? C19 C18 C30 117.0(7) . . ? C18 C19 C20 118.2(6) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? O6 C20 C15 115.8(5) . . ? O6 C20 C19 123.7(5) . . ? C15 C20 C19 120.5(6) . . ? O6 C21 C22 108.9(5) . . ? O6 C21 H21A 109.9 . . ? C22 C21 H21A 109.9 . . ? O6 C21 H21B 109.9 . . ? C22 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? O7 C22 C21 108.9(5) . . ? O7 C22 H22A 109.9 . . ? C21 C22 H22A 109.9 . . ? O7 C22 H22B 109.9 . . ? C21 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? O7 C23 C24 110.9(9) . . ? O7 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? O7 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? O8 C24 C23 113.6(9) . . ? O8 C24 H24A 108.8 . . ? C23 C24 H24A 108.8 . . ? O8 C24 H24B 108.8 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? O8 C25 C26 120.8(9) . . ? O8 C25 H25A 107.1 . . ? C26 C25 H25A 107.1 . . ? O8 C25 H25B 107.1 . . ? C26 C25 H25B 107.1 . . ? H25A C25 H25B 106.8 . . ? O9 C26 C25 114.5(7) . . ? O9 C26 H26A 108.6 . . ? C25 C26 H26A 108.6 . . ? O9 C26 H26B 108.6 . . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? O9 C27 C28 109.2(5) . . ? O9 C27 H27A 109.9 . . ? C28 C27 H27A 109.9 . . ? O9 C27 H27B 109.8 . . ? C28 C27 H27B 109.8 . . ? H27A C27 H27B 108.3 . . ? O10 C28 C27 106.9(5) . . ? O10 C28 H28A 110.3 . . ? C27 C28 H28A 110.3 . . ? O10 C28 H28B 110.3 . . ? C27 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? O11 C29 C4 108.5(5) . . ? O11 C29 H29A 110.0 . . ? C4 C29 H29A 110.0 . . ? O11 C29 H29B 110.0 . . ? C4 C29 H29B 110.0 . . ? H29A C29 H29B 108.4 . . ? O12 C30 C18 106.5(6) . . ? O12 C30 H30A 110.4 . . ? C18 C30 H30A 110.4 . . ? O12 C30 H30B 110.4 . . ? C18 C30 H30B 110.4 . . ? H30A C30 H30B 108.6 . . ? N1 C31 C32 119.2(5) . . ? N1 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C33 C32 C31 121.2(5) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 118.7(6) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 120.1(5) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? N1 C35 C34 119.0(4) . . ? N1 C35 C36 117.7(4) . . ? C34 C35 C36 123.3(4) . . ? N2 C36 C37 118.7(4) . . ? N2 C36 C35 119.8(4) . . ? C37 C36 C35 121.5(4) . . ? C36 C37 C38 119.2(5) . . ? C36 C37 H37 120.4 . . ? C38 C37 H37 120.4 . . ? C39 C38 C37 121.1(5) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 118.8(5) . . ? C38 C39 H39 120.6 . . ? C40 C39 H39 120.6 . . ? N2 C40 C39 120.5(5) . . ? N2 C40 H40 119.7 . . ? C39 C40 H40 119.8 . . ? N2 C41 C42 109.2(4) . . ? N2 C41 H41A 109.8 . . ? C42 C41 H41A 109.8 . . ? N2 C41 H41B 109.8 . . ? C42 C41 H41B 109.8 . . ? H41A C41 H41B 108.3 . . ? C41 C42 N1 108.8(4) . . ? C41 C42 H42A 109.9 . . ? N1 C42 H42A 109.9 . . ? C41 C42 H42B 109.9 . . ? N1 C42 H42B 109.9 . . ? H42A C42 H42B 108.3 . . ? 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 F6 P1 F1 H32 -153.2 . . . . ? F5 P1 F1 H32 25.1 . . . . ? F3 P1 F1 H32 47.5 . . . . ? F4 P1 F1 H32 -61.0 . . . . ? F2 P1 F1 H32 119.1 . . . . ? F8 P2 F11 H27A -57.3 . . . . ? F12 P2 F11 H27A -21.1 . . . . ? F10 P2 F11 H27A -147.3 . . . . ? F9 P2 F11 H27A 122.9 . . . . ? F7 P2 F11 H27A 34.8 . . . . ? C28 O10 C1 C2 8.9(8) . . . . ? C28 O10 C1 C6 -173.2(5) . . . . ? O10 C1 C2 C3 176.2(6) . . . . ? C6 C1 C2 C3 -1.7(8) . . . . ? C1 C2 C3 C4 -1.8(10) . . . . ? C2 C3 C4 C5 5.1(10) . . . . ? C2 C3 C4 C29 -170.3(6) . . . . ? C3 C4 C5 C6 -5.0(9) . . . . ? C29 C4 C5 C6 170.5(6) . . . . ? C7 O1 C6 C5 -6.8(8) . . . . ? C7 O1 C6 C1 173.6(5) . . . . ? C4 C5 C6 O1 -178.0(5) . . . . ? C4 C5 C6 C1 1.6(9) . . . . ? O10 C1 C6 O1 3.2(7) . . . . ? C2 C1 C6 O1 -178.6(5) . . . . ? O10 C1 C6 C5 -176.4(5) . . . . ? C2 C1 C6 C5 1.7(8) . . . . ? C6 O1 C7 C8 -175.3(5) . . . . ? C9 O2 C8 C7 -175.1(6) . . . . ? O1 C7 C8 O2 -67.2(7) . . . . ? C8 O2 C9 C10 -170.6(8) . . . . ? O2 C9 C10 O3 -60.7(13) . . . . ? C11 O3 C10 C9 -79.5(11) . . . . ? C10 O3 C11 C12 -166.0(7) . . . . ? C13 O4 C12 C11 178.7(6) . . . . ? O3 C11 C12 O4 -63.1(9) . . . . ? C12 O4 C13 C14 175.9(6) . . . . ? C15 O5 C14 C13 -174.9(5) . . . . ? O4 C13 C14 O5 73.7(7) . . . . ? C14 O5 C15 C16 8.7(8) . . . . ? C14 O5 C15 C20 -170.3(5) . . . . ? O5 C15 C16 C17 176.3(6) . . . . ? C20 C15 C16 C17 -4.7(9) . . . . ? C15 C16 C17 C18 2.8(10) . . . . ? C16 C17 C18 C19 -0.3(10) . . . . ? C16 C17 C18 C30 177.6(6) . . . . ? C17 C18 C19 C20 -0.3(9) . . . . ? C30 C18 C19 C20 -178.2(6) . . . . ? C21 O6 C20 C15 175.7(5) . . . . ? C21 O6 C20 C19 -4.4(7) . . . . ? C16 C15 C20 O6 -176.0(5) . . . . ? O5 C15 C20 O6 3.1(7) . . . . ? C16 C15 C20 C19 4.1(8) . . . . ? O5 C15 C20 C19 -176.8(5) . . . . ? C18 C19 C20 O6 178.4(5) . . . . ? C18 C19 C20 C15 -1.7(8) . . . . ? C20 O6 C21 C22 -173.9(5) . . . . ? C23 O7 C22 C21 168.6(8) . . . . ? O6 C21 C22 O7 -63.8(6) . . . . ? C22 O7 C23 C24 108.4(10) . . . . ? C25 O8 C24 C23 166.4(12) . . . . ? O7 C23 C24 O8 62.1(15) . . . . ? C24 O8 C25 C26 172.1(12) . . . . ? C27 O9 C26 C25 -176.1(10) . . . . ? O8 C25 C26 O9 -36(2) . . . . ? C26 O9 C27 C28 173.3(7) . . . . ? C1 O10 C28 C27 -176.1(5) . . . . ? O9 C27 C28 O10 75.6(7) . . . . ? C3 C4 C29 O11 84.9(8) . . . . ? C5 C4 C29 O11 -90.5(7) . . . . ? C17 C18 C30 O12 103.3(8) . . . . ? C19 C18 C30 O12 -78.8(8) . . . . ? C35 N1 C31 C32 0.3(8) . . . . ? C42 N1 C31 C32 -176.0(5) . . . . ? N1 C31 C32 C33 1.4(9) . . . . ? C31 C32 C33 C34 -3.8(9) . . . . ? C32 C33 C34 C35 4.7(9) . . . . ? C31 N1 C35 C34 0.7(7) . . . . ? C42 N1 C35 C34 176.9(5) . . . . ? C31 N1 C35 C36 -179.7(4) . . . . ? C42 N1 C35 C36 -3.4(7) . . . . ? C33 C34 C35 N1 -3.2(8) . . . . ? C33 C34 C35 C36 177.2(5) . . . . ? C40 N2 C36 C37 0.9(7) . . . . ? C41 N2 C36 C37 176.5(5) . . . . ? C40 N2 C36 C35 179.8(5) . . . . ? C41 N2 C36 C35 -4.6(6) . . . . ? N1 C35 C36 N2 -16.2(7) . . . . ? C34 C35 C36 N2 163.4(5) . . . . ? N1 C35 C36 C37 162.6(5) . . . . ? C34 C35 C36 C37 -17.7(7) . . . . ? N2 C36 C37 C38 -1.2(7) . . . . ? C35 C36 C37 C38 179.9(5) . . . . ? C36 C37 C38 C39 1.0(8) . . . . ? C37 C38 C39 C40 -0.4(8) . . . . ? C36 N2 C40 C39 -0.3(8) . . . . ? C41 N2 C40 C39 -175.9(5) . . . . ? C38 C39 C40 N2 0.1(8) . . . . ? C36 N2 C41 C42 42.1(6) . . . . ? C40 N2 C41 C42 -142.2(5) . . . . ? N2 C41 C42 N1 -57.7(5) . . . . ? C31 N1 C42 C41 -143.1(5) . . . . ? C35 N1 C42 C41 40.5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O3 0.82 2.27 3.027(8) 154.0 3_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.551 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.065 #===END