Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'John Rutherford' 'Selen Bilge' 'Simon Coles' 'David B. Davies' 'M. Hursthouse' 'Zeynel Kilic' 'Robert A. Shaw' _publ_contact_author_name 'John Rutherford' _publ_contact_author_address ; 1 Barliath Minard Argyll PA32 8YQ UNITED KINGDOM ; _publ_contact_author_email JOHN.RUTHERFORD9@BTINTERNET.COM _publ_requested_journal CrystEngComm _publ_section_title ; Clathrate and channel inclusion systems co-exist in the crystal structure of a bis-C-pivot lariat ether. ; data_03src0788 _database_code_depnum_ccdc_archive 'CCDC 666066' _audit_update_record ; 2007-07-27 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 15,22-bis(dimethoxyphosphoryl)-2,5,8-trioxa- 16,21-diazatricyclo[21.4.0.0^9,14^]heptacosa- 9,11,13,23,25,27(1)-hexaene tetrahydrofuran methanol ; _chemical_formula_moiety 'C26 H40 N2 O9 P2, C4 H8 O, C H4 O' _chemical_formula_sum 'C31 H52 N2 O11 P2' _chemical_formula_weight 690.69 _chemical_compound_source 'synthesis as described' 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' 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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 16.6305(4) _cell_length_b 16.7308(5) _cell_length_c 24.0702(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6697.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.370 _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5927 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 35912 _diffrn_reflns_av_R_equivalents 0.2078 _diffrn_reflns_av_sigmaI/netI 0.1746 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.56 _reflns_number_total 14109 _reflns_number_gt 9597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF (Buerskens et al., 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _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^)+(0.1408P)^2^+8.9372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary vecmap _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0198(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Crystal was refined as an inversion twin. Refined fraction of inverted component 0.38(15) ; _refine_ls_number_reflns 14109 _refine_ls_number_parameters 797 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1371 _refine_ls_R_factor_gt 0.0893 _refine_ls_wR_factor_ref 0.2658 _refine_ls_wR_factor_gt 0.2263 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.017 _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 _atom_site_attached_hydrogens C1 C 0.0820(4) -0.0146(4) 0.2630(3) 0.0297(14) Uani 1 1 d . . . . O2 O 0.1144(3) -0.0844(3) 0.2820(2) 0.0376(12) Uani 1 1 d . . . . C3 C 0.1019(4) -0.1020(5) 0.3393(3) 0.0391(17) Uani 1 1 d . . . . H3A H 0.0449 -0.1089 0.3464 0.047 Uiso 1 1 calc R . . . H3B H 0.1211 -0.0579 0.3619 0.047 Uiso 1 1 calc R . . . C4 C 0.1463(4) -0.1772(5) 0.3546(3) 0.0420(18) Uani 1 1 d . . . . H4A H 0.2017 -0.1728 0.3424 0.050 Uiso 1 1 calc R . . . H4B H 0.1463 -0.1832 0.3947 0.050 Uiso 1 1 calc R . . . O5 O 0.1113(3) -0.2453(3) 0.3303(2) 0.0378(12) Uani 1 1 d . . . . C6 C 0.1536(4) -0.3153(5) 0.3476(3) 0.0432(19) Uani 1 1 d . . . . H6A H 0.1554 -0.3170 0.3878 0.052 Uiso 1 1 calc R . . . H6B H 0.2085 -0.3128 0.3340 0.052 Uiso 1 1 calc R . . . C7 C 0.1149(5) -0.3896(5) 0.3265(3) 0.0431(18) Uani 1 1 d . . . . H7A H 0.1385 -0.4358 0.3446 0.052 Uiso 1 1 calc R . . . H7B H 0.0579 -0.3887 0.3349 0.052 Uiso 1 1 calc R . . . O8 O 0.1265(3) -0.3952(3) 0.2677(2) 0.0401(12) Uani 1 1 d . . . . C9 C 0.1033(4) -0.4652(5) 0.2425(3) 0.0381(17) Uani 1 1 d . . . . C10 C 0.0678(4) -0.5283(5) 0.2709(3) 0.0417(18) Uani 1 1 d . . . . H10 H 0.0583 -0.5246 0.3089 0.050 Uiso 1 1 calc R . . . C11 C 0.0468(4) -0.5969(5) 0.2421(3) 0.0438(19) Uani 1 1 d . . . . H11 H 0.0249 -0.6400 0.2612 0.053 Uiso 1 1 calc R . . . C12 C 0.0579(4) -0.6018(5) 0.1862(3) 0.0404(17) Uani 1 1 d . . . . H12 H 0.0429 -0.6480 0.1674 0.049 Uiso 1 1 calc R . . . C13 C 0.0916(4) -0.5385(4) 0.1571(3) 0.0325(15) Uani 1 1 d . . . . H13 H 0.0979 -0.5421 0.1188 0.039 Uiso 1 1 calc R . . . C14 C 0.1160(4) -0.4692(4) 0.1850(3) 0.0296(14) Uani 1 1 d . . . . C15 C 0.1517(3) -0.4002(4) 0.1529(3) 0.0294(14) Uani 1 1 d D . . . H15 H 0.1674 -0.3596 0.1802 0.035 Uiso 1 1 calc R . . . N16 N 0.0995(3) -0.3602(3) 0.1121(2) 0.0290(12) Uani 1 1 d D . . . H16 H 0.084(3) -0.395(3) 0.0871(17) 0.035 Uiso 1 1 d D . . . C17 C 0.0244(4) -0.3294(4) 0.1369(3) 0.0282(13) Uani 1 1 d D . . . H17A H 0.0360 -0.3060 0.1729 0.034 Uiso 1 1 calc R . . . H17B H -0.0129 -0.3732 0.1425 0.034 Uiso 1 1 calc R . . . C18 C -0.0138(4) -0.2667(4) 0.0994(3) 0.0297(14) Uani 1 1 d . . . . H18A H -0.0287 -0.2920 0.0646 0.036 Uiso 1 1 calc R . . . H18B H -0.0629 -0.2479 0.1169 0.036 Uiso 1 1 calc R . . . C19 C 0.0391(4) -0.1951(4) 0.0868(3) 0.0284(13) Uani 1 1 d . . . . H19A H 0.0837 -0.2123 0.0637 0.034 Uiso 1 1 calc R . . . H19B H 0.0082 -0.1564 0.0657 0.034 Uiso 1 1 calc R . . . C20 C 0.0719(4) -0.1550(4) 0.1385(3) 0.0293(14) Uani 1 1 d D . . . H20A H 0.0276 -0.1380 0.1619 0.035 Uiso 1 1 calc R . . . H20B H 0.1039 -0.1931 0.1594 0.035 Uiso 1 1 calc R . . . N21 N 0.1219(3) -0.0853(3) 0.1240(2) 0.0263(11) Uani 1 1 d D . . . H21 H 0.091(3) -0.0497(19) 0.1074(19) 0.032 Uiso 1 1 d D . . . C22 C 0.1575(4) -0.0476(4) 0.1725(3) 0.0276(13) Uani 1 1 d D . . . H22 H 0.1775 -0.0904 0.1967 0.033 Uiso 1 1 calc R . . . C23 C 0.1031(4) 0.0058(4) 0.2077(3) 0.0295(14) Uani 1 1 d . . . . C24 C 0.0714(4) 0.0756(4) 0.1854(3) 0.0336(15) Uani 1 1 d . . . . H24 H 0.0832 0.0893 0.1488 0.040 Uiso 1 1 calc R . . . C25 C 0.0224(4) 0.1251(5) 0.2170(4) 0.0444(19) Uani 1 1 d . . . . H25 H 0.0020 0.1718 0.2015 0.053 Uiso 1 1 calc R . . . C26 C 0.0038(4) 0.1054(5) 0.2713(3) 0.0445(19) Uani 1 1 d . . . . H26 H -0.0287 0.1389 0.2926 0.053 Uiso 1 1 calc R . . . C27 C 0.0339(4) 0.0356(5) 0.2937(3) 0.0416(18) Uani 1 1 d . . . . H27 H 0.0215 0.0222 0.3302 0.050 Uiso 1 1 calc R . . . P28 P 0.24164(9) -0.42688(10) 0.11491(7) 0.0275(4) Uani 1 1 d . . . . O29 O 0.2272(3) -0.4796(3) 0.06699(18) 0.0311(10) Uani 1 1 d . . . . O30 O 0.2988(3) -0.4605(3) 0.16171(18) 0.0342(11) Uani 1 1 d . . . . C31 C 0.3763(4) -0.4925(5) 0.1457(4) 0.0447(18) Uani 1 1 d . . . . H31A H 0.4044 -0.5107 0.1782 0.054 Uiso 1 1 calc R . . . H31B H 0.4073 -0.4516 0.1277 0.054 Uiso 1 1 calc R . . . H31C H 0.3687 -0.5365 0.1206 0.054 Uiso 1 1 calc R . . . O32 O 0.2859(3) -0.3461(3) 0.09906(19) 0.0341(10) Uani 1 1 d . . . . C33 C 0.2704(5) -0.3096(5) 0.0455(3) 0.0436(18) Uani 1 1 d . . . . H33A H 0.3015 -0.2615 0.0421 0.052 Uiso 1 1 calc R . . . H33B H 0.2143 -0.2971 0.0424 0.052 Uiso 1 1 calc R . . . H33C H 0.2853 -0.3461 0.0165 0.052 Uiso 1 1 calc R . . . P34 P 0.24406(9) 0.00506(10) 0.14583(7) 0.0265(4) Uani 1 1 d . . . . O35 O 0.2285(3) 0.0616(3) 0.10039(19) 0.0304(10) Uani 1 1 d . . . . O36 O 0.3078(3) -0.0612(3) 0.1310(2) 0.0334(11) Uani 1 1 d . . . . C37 C 0.3116(5) -0.0906(5) 0.0742(4) 0.050(2) Uani 1 1 d . . . . H37A H 0.3532 -0.1301 0.0713 0.060 Uiso 1 1 calc R . . . H37B H 0.3233 -0.0470 0.0495 0.060 Uiso 1 1 calc R . . . H37C H 0.2609 -0.1140 0.0642 0.060 Uiso 1 1 calc R . . . O38 O 0.2813(3) 0.0412(3) 0.20039(19) 0.0367(11) Uani 1 1 d . . . . C39 C 0.3586(5) 0.0808(6) 0.1991(4) 0.052(2) Uani 1 1 d . . . . H39A H 0.3722 0.0988 0.2358 0.062 Uiso 1 1 calc R . . . H39B H 0.3560 0.1259 0.1744 0.062 Uiso 1 1 calc R . . . H39C H 0.3989 0.0442 0.1862 0.062 Uiso 1 1 calc R . . . C67 C -0.2118(4) 0.4867(5) 0.3296(3) 0.0429(18) Uani 1 1 d . . . . H67 H -0.2291 0.5043 0.2949 0.052 Uiso 1 1 calc R . . . C66 C -0.2395(4) 0.4148(5) 0.3499(3) 0.0423(18) Uani 1 1 d . . . . H66 H -0.2743 0.3837 0.3288 0.051 Uiso 1 1 calc R . . . C65 C -0.2152(4) 0.3894(5) 0.4017(3) 0.0399(17) Uani 1 1 d . . . . H65 H -0.2331 0.3405 0.4154 0.048 Uiso 1 1 calc R . . . C64 C -0.1646(4) 0.4360(4) 0.4334(3) 0.0297(14) Uani 1 1 d . . . . H64 H -0.1508 0.4195 0.4690 0.036 Uiso 1 1 calc R . . . C63 C -0.1336(3) 0.5081(4) 0.4126(3) 0.0265(13) Uani 1 1 d . . . . C62 C -0.0791(3) 0.5591(4) 0.4483(3) 0.0245(12) Uani 1 1 d D . . . H62 H -0.0577 0.6018 0.4247 0.029 Uiso 1 1 calc R . . . N61 N -0.1179(3) 0.5975(3) 0.4966(2) 0.0245(11) Uani 1 1 d D . . . H61 H -0.152(2) 0.5605(19) 0.509(2) 0.029 Uiso 1 1 d D . . . C60 C -0.1681(4) 0.6642(4) 0.4786(3) 0.0274(13) Uani 1 1 d D . . . H60A H -0.2088 0.6451 0.4530 0.033 Uiso 1 1 calc R . . . H60B H -0.1352 0.7032 0.4592 0.033 Uiso 1 1 calc R . . . C59 C -0.2083(4) 0.7036(4) 0.5283(3) 0.0303(14) Uani 1 1 d . . . . H59A H -0.1671 0.7221 0.5538 0.036 Uiso 1 1 calc R . . . H59B H -0.2405 0.6640 0.5476 0.036 Uiso 1 1 calc R . . . C58 C -0.2619(4) 0.7739(4) 0.5125(3) 0.0302(14) Uani 1 1 d . . . . H58A H -0.2801 0.8000 0.5462 0.036 Uiso 1 1 calc R . . . H58B H -0.3089 0.7537 0.4933 0.036 Uiso 1 1 calc R . . . C57 C -0.2207(4) 0.8357(4) 0.4757(3) 0.0330(14) Uani 1 1 d D . . . H57A H -0.2077 0.8116 0.4401 0.040 Uiso 1 1 calc R . . . H57B H -0.2573 0.8798 0.4689 0.040 Uiso 1 1 calc R . . . N56 N -0.1470(3) 0.8663(3) 0.5013(2) 0.0275(11) Uani 1 1 d D . . . H56 H -0.161(3) 0.897(3) 0.5291(15) 0.033 Uiso 1 1 d D . . . C55 C -0.0941(3) 0.9090(4) 0.4627(3) 0.0273(13) Uani 1 1 d D . . . H55 H -0.0795 0.8715 0.4330 0.033 Uiso 1 1 calc R . . . C54 C -0.1307(3) 0.9830(4) 0.4350(3) 0.0246(13) Uani 1 1 d . . . . C53 C -0.1514(4) 1.0503(4) 0.4663(3) 0.0286(13) Uani 1 1 d . . . . H53 H -0.1430 1.0507 0.5045 0.034 Uiso 1 1 calc R . . . C52 C -0.1848(4) 1.1170(4) 0.4402(3) 0.0359(16) Uani 1 1 d . . . . H52 H -0.1981 1.1620 0.4609 0.043 Uiso 1 1 calc R . . . C51 C -0.1979(4) 1.1161(5) 0.3840(3) 0.0417(18) Uani 1 1 d . . . . H51 H -0.2194 1.1611 0.3669 0.050 Uiso 1 1 calc R . . . C50 C -0.1798(4) 1.0503(5) 0.3527(3) 0.0393(17) Uani 1 1 d . . . . H50 H -0.1897 1.0503 0.3147 0.047 Uiso 1 1 calc R . . . C49 C -0.1463(4) 0.9831(4) 0.3782(3) 0.0320(14) Uani 1 1 d . . . . O48 O -0.1239(3) 0.9158(3) 0.34975(19) 0.0353(11) Uani 1 1 d . . . . C47 C -0.1428(5) 0.9108(5) 0.2915(3) 0.0395(17) Uani 1 1 d . . . . H47A H -0.1229 0.9579 0.2724 0.047 Uiso 1 1 calc R . . . H47B H -0.2006 0.9082 0.2864 0.047 Uiso 1 1 calc R . . . C46 C -0.1047(5) 0.8385(5) 0.2683(3) 0.0396(17) Uani 1 1 d . . . . H46A H -0.1112 0.8384 0.2283 0.048 Uiso 1 1 calc R . . . H46B H -0.0475 0.8398 0.2763 0.048 Uiso 1 1 calc R . . . O45 O -0.1382(3) 0.7672(3) 0.2906(2) 0.0352(11) Uani 1 1 d . . . . C44 C -0.0975(4) 0.6994(5) 0.2689(3) 0.0399(17) Uani 1 1 d . . . . H44A H -0.0431 0.6979 0.2833 0.048 Uiso 1 1 calc R . . . H44B H -0.0945 0.7036 0.2287 0.048 Uiso 1 1 calc R . . . C43 C -0.1402(4) 0.6243(5) 0.2843(3) 0.0377(16) Uani 1 1 d . . . . H43A H -0.1973 0.6307 0.2777 0.045 Uiso 1 1 calc R . . . H43B H -0.1211 0.5809 0.2611 0.045 Uiso 1 1 calc R . . . O42 O -0.1269(3) 0.6048(3) 0.3418(2) 0.0374(11) Uani 1 1 d . . . . C41 C -0.1585(4) 0.5333(4) 0.3599(3) 0.0318(15) Uani 1 1 d . . . . P68 P -0.00430(9) 0.93040(10) 0.50150(7) 0.0266(4) Uani 1 1 d . . . . O69 O -0.0164(3) 0.9743(3) 0.55392(19) 0.0324(10) Uani 1 1 d . . . . O70 O 0.0504(3) 0.9719(3) 0.45741(18) 0.0320(10) Uani 1 1 d . . . . C71 C 0.1293(4) 1.0020(5) 0.4755(3) 0.0431(18) Uani 1 1 d . . . . H71A H 0.1565 1.0261 0.4445 0.052 Uiso 1 1 calc R . . . H71B H 0.1610 0.9584 0.4895 0.052 Uiso 1 1 calc R . . . H71C H 0.1220 1.0410 0.5043 0.052 Uiso 1 1 calc R . . . O72 O 0.0402(3) 0.8483(3) 0.5092(2) 0.0370(11) Uani 1 1 d . . . . C73 C 0.0255(5) 0.7990(6) 0.5573(4) 0.063(3) Uani 1 1 d . . . . H73A H 0.0579 0.7516 0.5552 0.076 Uiso 1 1 calc R . . . H73B H -0.0303 0.7844 0.5585 0.076 Uiso 1 1 calc R . . . H73C H 0.0392 0.8283 0.5903 0.076 Uiso 1 1 calc R . . . P74 P 0.00580(9) 0.50458(10) 0.47618(7) 0.0259(4) Uani 1 1 d . . . . O75 O -0.0120(3) 0.4418(3) 0.51625(19) 0.0319(11) Uani 1 1 d . . . . O76 O 0.0664(2) 0.5691(3) 0.4987(2) 0.0309(10) Uani 1 1 d . . . . C77 C 0.0698(5) 0.5850(4) 0.5578(3) 0.0383(16) Uani 1 1 d . . . . H77A H 0.1091 0.6258 0.5649 0.046 Uiso 1 1 calc R . . . H77B H 0.0846 0.5371 0.5772 0.046 Uiso 1 1 calc R . . . H77C H 0.0181 0.6028 0.5704 0.046 Uiso 1 1 calc R . . . O78 O 0.0483(3) 0.4768(3) 0.42092(19) 0.0334(10) Uani 1 1 d . . . . C79 C 0.1250(4) 0.4349(5) 0.4240(3) 0.0392(17) Uani 1 1 d . . . . H79A H 0.1430 0.4220 0.3872 0.047 Uiso 1 1 calc R . . . H79B H 0.1185 0.3866 0.4451 0.047 Uiso 1 1 calc R . . . H79C H 0.1641 0.4685 0.4418 0.047 Uiso 1 1 calc R . . . O81 O 0.5458(4) 0.2229(4) 0.3502(3) 0.0565(15) Uani 1 1 d . . . . C82 C 0.4689(5) 0.2059(5) 0.3734(3) 0.0469(19) Uani 1 1 d . . . . H82A H 0.4580 0.1490 0.3716 0.056 Uiso 1 1 calc R . . . H82B H 0.4273 0.2339 0.3530 0.056 Uiso 1 1 calc R . . . C83 C 0.4705(5) 0.2332(5) 0.4322(3) 0.0438(18) Uani 1 1 d . . . . H83A H 0.4920 0.1922 0.4564 0.053 Uiso 1 1 calc R . . . H83B H 0.4171 0.2479 0.4449 0.053 Uiso 1 1 calc R . . . C84 C 0.5249(6) 0.3044(5) 0.4297(4) 0.055(2) Uani 1 1 d . . . . H84A H 0.5505 0.3140 0.4653 0.066 Uiso 1 1 calc R . . . H84B H 0.4958 0.3520 0.4185 0.066 Uiso 1 1 calc R . . . C85 C 0.5862(5) 0.2795(5) 0.3858(4) 0.053(2) Uani 1 1 d . . . . H85A H 0.6039 0.3255 0.3646 0.063 Uiso 1 1 calc R . . . H85B H 0.6328 0.2550 0.4031 0.063 Uiso 1 1 calc R . . . O91 O 0.7682(6) 0.2282(6) 0.2610(4) 0.101(3) Uani 1 1 d . . . . C92 C 0.7021(7) 0.2659(6) 0.2355(4) 0.067(3) Uani 1 1 d . . . . H92A H 0.7018 0.3226 0.2438 0.081 Uiso 1 1 calc R . . . H92B H 0.6520 0.2427 0.2485 0.081 Uiso 1 1 calc R . . . C93 C 0.7119(6) 0.2524(5) 0.1748(4) 0.056(2) Uani 1 1 d . . . . H93A H 0.6606 0.2392 0.1579 0.068 Uiso 1 1 calc R . . . 93B H 0.7331 0.2999 0.1570 0.068 Uiso 1 1 calc R . . . C94 C 0.7690(9) 0.1849(7) 0.1691(5) 0.087(4) Uani 1 1 d . . . . H94A H 0.8193 0.2026 0.1528 0.105 Uiso 1 1 calc R . . . H94B H 0.7465 0.1429 0.1461 0.105 Uiso 1 1 calc R . . . C95 C 0.7811(8) 0.1568(9) 0.2270(5) 0.095(4) Uani 1 1 d . . . . H95A H 0.7426 0.1153 0.2364 0.114 Uiso 1 1 calc R . . . H95B H 0.8350 0.1360 0.2321 0.114 Uiso 1 1 calc R . . . O101 O 0.24 0.77 0.40 1.000 Uiso 1 1 dum . . . 1 C101 C 0.29 0.73 0.41 1.000 Uiso 1 1 dum . . . 3 C111 C 0.03 0.72 0.22 1.000 Uiso 1 1 dum . . . 3 O111 O -0.01 0.78 0.22 1.000 Uiso 1 1 dum . . . 1 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 0.030(3) 0.036(4) 0.023(3) -0.001(3) 0.004(2) -0.009(3) O2 0.044(3) 0.051(3) 0.018(2) 0.001(2) 0.0072(19) -0.004(2) C3 0.039(4) 0.057(5) 0.021(3) -0.002(3) 0.008(3) -0.006(3) C4 0.035(4) 0.073(5) 0.018(3) 0.003(3) -0.002(3) -0.013(4) O5 0.033(2) 0.059(3) 0.021(3) 0.003(2) -0.0031(19) 0.003(2) C6 0.034(4) 0.076(6) 0.020(3) 0.001(4) -0.003(3) 0.017(4) C7 0.044(4) 0.059(5) 0.026(4) 0.009(4) -0.001(3) 0.006(4) O8 0.041(3) 0.053(3) 0.027(3) 0.000(2) 0.001(2) 0.001(2) C9 0.026(3) 0.060(5) 0.029(4) 0.011(3) -0.004(3) 0.004(3) C10 0.034(4) 0.061(5) 0.030(4) 0.017(4) 0.000(3) 0.000(3) C11 0.030(3) 0.057(5) 0.044(4) 0.024(4) -0.007(3) -0.005(3) C12 0.031(4) 0.041(4) 0.049(5) 0.010(4) -0.009(3) -0.005(3) C13 0.029(3) 0.042(4) 0.027(4) 0.008(3) 0.004(3) 0.002(3) C14 0.025(3) 0.037(4) 0.026(3) 0.006(3) -0.003(2) 0.000(3) C15 0.021(3) 0.039(4) 0.028(3) -0.003(3) 0.003(2) 0.002(3) N16 0.025(2) 0.041(3) 0.021(3) 0.002(2) -0.004(2) 0.004(2) C17 0.028(3) 0.028(3) 0.028(3) -0.007(3) 0.003(2) 0.001(3) C18 0.025(3) 0.032(3) 0.032(4) -0.003(3) -0.002(2) 0.005(3) C19 0.025(3) 0.034(3) 0.027(3) -0.001(3) -0.005(2) 0.000(3) C20 0.031(3) 0.030(3) 0.027(3) 0.006(3) -0.003(3) -0.006(3) N21 0.030(3) 0.028(3) 0.020(3) -0.004(2) -0.001(2) -0.002(2) C22 0.024(3) 0.036(3) 0.023(3) -0.004(3) 0.003(2) -0.003(3) C23 0.027(3) 0.040(4) 0.022(3) -0.006(3) 0.006(2) -0.005(3) C24 0.039(4) 0.035(4) 0.027(4) 0.001(3) 0.004(3) 0.001(3) C25 0.036(4) 0.041(4) 0.056(5) -0.014(4) 0.006(3) -0.005(3) C26 0.036(4) 0.055(5) 0.042(4) -0.018(4) 0.010(3) -0.007(3) C27 0.042(4) 0.055(5) 0.028(4) -0.010(4) 0.009(3) -0.011(4) P28 0.0236(8) 0.0346(9) 0.0241(8) -0.0019(7) 0.0005(6) 0.0001(7) O29 0.032(2) 0.035(2) 0.026(2) -0.006(2) 0.0027(18) -0.0025(19) O30 0.028(2) 0.048(3) 0.027(3) -0.003(2) -0.0007(18) 0.004(2) C31 0.030(3) 0.061(5) 0.043(4) 0.002(4) 0.003(3) 0.013(3) O32 0.032(2) 0.038(2) 0.032(3) 0.005(2) 0.0023(19) -0.009(2) C33 0.046(4) 0.041(4) 0.044(4) 0.004(3) 0.006(3) -0.009(3) P34 0.0232(7) 0.0345(9) 0.0218(8) 0.0021(7) 0.0002(6) -0.0007(6) O35 0.033(2) 0.033(2) 0.026(2) 0.0057(19) -0.0033(18) -0.0002(19) O36 0.035(2) 0.032(2) 0.034(3) 0.002(2) 0.0022(19) 0.0100(19) C37 0.047(4) 0.044(4) 0.058(5) -0.023(4) 0.011(4) 0.011(4) O38 0.026(2) 0.062(3) 0.023(2) -0.001(2) -0.0025(17) -0.013(2) C39 0.042(4) 0.075(6) 0.038(4) -0.002(4) -0.003(3) -0.023(4) C67 0.036(4) 0.067(5) 0.026(4) -0.005(4) 0.000(3) -0.007(4) C66 0.028(3) 0.060(5) 0.040(4) -0.023(4) -0.001(3) -0.004(3) C65 0.033(4) 0.041(4) 0.045(4) -0.015(3) 0.004(3) -0.006(3) C64 0.027(3) 0.039(4) 0.023(3) -0.002(3) 0.000(2) -0.002(3) C63 0.021(3) 0.034(3) 0.024(3) -0.003(3) 0.001(2) 0.004(2) C62 0.022(3) 0.028(3) 0.023(3) 0.004(3) -0.001(2) 0.002(2) N61 0.029(3) 0.024(2) 0.020(3) -0.002(2) 0.000(2) 0.002(2) C60 0.029(3) 0.029(3) 0.024(3) -0.003(3) -0.004(2) 0.003(2) C59 0.034(3) 0.029(3) 0.027(3) -0.003(3) 0.009(3) -0.001(3) C58 0.032(3) 0.027(3) 0.032(4) -0.004(3) 0.002(3) 0.001(3) C57 0.030(3) 0.031(3) 0.037(4) 0.004(3) -0.003(3) 0.005(3) N56 0.025(2) 0.034(3) 0.024(3) 0.002(2) 0.005(2) -0.005(2) C55 0.022(3) 0.034(3) 0.026(3) 0.003(3) -0.001(2) 0.002(2) C54 0.017(3) 0.028(3) 0.028(3) 0.007(3) -0.001(2) -0.003(2) C53 0.027(3) 0.030(3) 0.029(3) -0.003(3) -0.005(2) 0.001(3) C52 0.027(3) 0.033(4) 0.047(4) 0.003(3) 0.003(3) -0.003(3) C51 0.029(3) 0.042(4) 0.054(5) 0.018(4) 0.001(3) -0.003(3) C50 0.034(4) 0.053(5) 0.031(4) 0.011(4) 0.003(3) 0.001(3) C49 0.029(3) 0.039(4) 0.028(4) 0.001(3) 0.001(3) -0.003(3) O48 0.044(3) 0.048(3) 0.014(2) 0.001(2) -0.0009(18) 0.004(2) C47 0.044(4) 0.060(5) 0.014(3) -0.002(3) -0.001(3) -0.012(3) C46 0.045(4) 0.046(4) 0.028(4) 0.001(3) 0.004(3) -0.004(3) O45 0.032(2) 0.046(3) 0.027(3) 0.003(2) 0.0044(19) 0.001(2) C44 0.040(4) 0.053(4) 0.027(4) 0.010(3) 0.008(3) 0.010(3) C43 0.043(4) 0.050(4) 0.019(3) 0.000(3) -0.002(3) 0.008(3) O42 0.046(3) 0.042(3) 0.024(2) -0.001(2) -0.008(2) -0.004(2) C41 0.033(3) 0.035(4) 0.027(3) -0.010(3) 0.000(3) 0.006(3) P68 0.0214(7) 0.0350(9) 0.0235(8) -0.0012(7) 0.0010(6) 0.0012(6) O69 0.027(2) 0.043(3) 0.027(2) -0.004(2) 0.0012(18) 0.000(2) O70 0.026(2) 0.044(3) 0.026(2) -0.004(2) 0.0011(17) -0.008(2) C71 0.030(3) 0.064(5) 0.035(4) -0.010(4) 0.004(3) -0.015(3) O72 0.030(2) 0.040(3) 0.041(3) 0.001(2) 0.000(2) 0.007(2) C73 0.047(5) 0.062(6) 0.081(7) 0.029(5) 0.006(4) 0.014(4) P74 0.0256(8) 0.0297(8) 0.0223(8) 0.0028(7) -0.0001(6) 0.0008(6) O75 0.035(2) 0.027(2) 0.035(3) 0.005(2) -0.0015(19) 0.0007(19) O76 0.027(2) 0.030(2) 0.036(3) 0.002(2) -0.0070(19) -0.0077(18) C77 0.051(4) 0.032(4) 0.032(4) -0.007(3) -0.012(3) -0.008(3) O78 0.029(2) 0.045(3) 0.026(2) 0.004(2) 0.0009(18) 0.007(2) C79 0.031(3) 0.044(4) 0.043(4) 0.000(3) -0.003(3) 0.009(3) O81 0.062(4) 0.062(4) 0.045(3) -0.004(3) 0.016(3) -0.004(3) C82 0.050(4) 0.044(4) 0.047(5) 0.009(4) 0.000(4) -0.004(4) C83 0.044(4) 0.044(4) 0.044(5) 0.000(4) 0.005(3) 0.004(3) C84 0.061(5) 0.038(4) 0.065(6) 0.001(4) 0.011(4) -0.001(4) C85 0.042(4) 0.049(5) 0.066(6) 0.012(4) 0.005(4) -0.017(4) O91 0.120(7) 0.126(8) 0.059(5) 0.008(5) -0.022(5) 0.011(6) C92 0.091(7) 0.057(6) 0.054(6) 0.002(5) -0.003(5) -0.004(5) C93 0.083(6) 0.039(4) 0.046(5) 0.000(4) -0.002(4) -0.001(4) C94 0.128(10) 0.074(7) 0.060(7) 0.009(6) 0.009(7) 0.031(7) C95 0.093(8) 0.114(11) 0.077(8) 0.029(8) -0.012(6) 0.027(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.365(9) . n C1 C27 1.375(10) . n C1 C23 1.417(9) . n O2 C3 1.426(8) . n C3 C4 1.504(11) . n C4 O5 1.406(9) . n O5 C6 1.428(9) . n C6 C7 1.488(12) . n C7 O8 1.433(9) . n O8 C9 1.374(10) . n C9 C10 1.389(11) . n C9 C14 1.401(10) . n C10 C11 1.385(12) . n C11 C12 1.360(11) . n C12 C13 1.389(10) . n C13 C14 1.400(10) . n C14 C15 1.511(9) . n C15 N16 1.472(8) . n C15 P28 1.809(6) . n N16 C17 1.477(8) . n C17 C18 1.523(9) . n C18 C19 1.518(9) . n C19 C20 1.516(9) . n C20 N21 1.474(8) . n N21 C22 1.453(8) . n C22 C23 1.529(9) . n C22 P34 1.806(6) . n C23 C24 1.388(10) . n C24 C25 1.389(10) . n C25 C26 1.385(12) . n C26 C27 1.380(12) . n P28 O29 1.472(5) . n P28 O30 1.577(5) . n P28 O32 1.585(5) . n O30 C31 1.449(8) . n O32 C33 1.450(9) . n P34 O35 1.469(5) . n P34 O38 1.572(5) . n P34 O36 1.574(5) . n O36 C37 1.455(9) . n O38 C39 1.448(8) . n C67 C41 1.388(10) . n C67 C66 1.378(12) . n C66 C65 1.378(12) . n C65 C64 1.378(10) . n C64 C63 1.404(9) . n C63 C41 1.397(9) . n C63 C62 1.514(9) . n C62 N61 1.476(8) . n C62 P74 1.811(6) . n N61 C60 1.459(8) . n C60 C59 1.521(8) . n C59 C58 1.524(9) . n C58 C57 1.525(9) . n C57 N56 1.464(8) . n N56 C55 1.466(8) . n C55 C54 1.532(9) . n C55 P68 1.798(6) . n C54 C49 1.392(9) . n C54 C53 1.399(9) . n C53 C52 1.395(9) . n C52 C51 1.369(11) . n C51 C50 1.368(11) . n C50 C49 1.397(10) . n C49 O48 1.369(9) . n O48 C47 1.440(8) . n C47 C46 1.475(11) . n C46 O45 1.421(9) . n O45 C44 1.421(9) . n C44 C43 1.489(11) . n C43 O42 1.439(8) . n O42 C41 1.378(9) . n P68 O69 1.474(5) . n P68 O70 1.561(5) . n P68 O72 1.572(5) . n O70 C71 1.471(8) . n O72 C73 1.442(10) . n P74 O75 1.456(5) . n P74 O76 1.574(4) . n P74 O78 1.576(5) . n O76 C77 1.448(8) . n O78 C79 1.457(8) . n O81 C82 1.423(10) . n O81 C85 1.443(10) . n C82 C83 1.486(11) . n C83 C84 1.497(12) . n C84 C85 1.528(12) . n O91 C92 1.409(13) . n O91 C95 1.465(17) . n C92 C93 1.487(12) . n C93 C94 1.482(14) . n C94 C95 1.485(15) . n 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 O2 C1 C27 124.8(6) . . n O2 C1 C23 115.1(6) . . n C27 C1 C23 120.0(7) . . n C1 O2 C3 116.4(6) . . n O2 C3 C4 109.7(6) . . n O5 C4 C3 111.9(6) . . n C4 O5 C6 110.0(5) . . n O5 C6 C7 112.0(6) . . n O8 C7 C6 109.4(6) . . n C9 O8 C7 117.0(6) . . n O8 C9 C10 123.4(7) . . n O8 C9 C14 115.7(7) . . n C10 C9 C14 120.9(8) . . n C11 C10 C9 119.4(7) . . n C12 C11 C10 120.7(7) . . n C11 C12 C13 120.5(8) . . n C12 C13 C14 120.4(7) . . n C13 C14 C9 118.0(6) . . n C13 C14 C15 120.1(6) . . n C9 C14 C15 121.8(7) . . n N16 C15 C14 117.1(5) . . n N16 C15 P28 105.2(4) . . n C14 C15 P28 113.3(5) . . n C15 N16 C17 112.8(5) . . n N16 C17 C18 110.7(5) . . n C19 C18 C17 114.9(5) . . n C20 C19 C18 113.1(5) . . n N21 C20 C19 111.1(5) . . n C22 N21 C20 112.6(5) . . n N21 C22 C23 117.2(5) . . n N21 C22 P34 104.5(4) . . n C23 C22 P34 112.6(4) . . n C24 C23 C1 118.2(6) . . n C24 C23 C22 120.1(6) . . n C1 C23 C22 121.6(6) . . n C25 C24 C23 120.8(7) . . n C24 C25 C26 120.4(8) . . n C27 C26 C25 119.2(7) . . n C1 C27 C26 121.3(7) . . n O29 P28 O30 116.4(3) . . n O29 P28 O32 113.5(3) . . n O30 P28 O32 101.3(3) . . n O29 P28 C15 114.2(3) . . n O30 P28 C15 103.0(3) . . n O32 P28 C15 107.1(3) . . n C31 O30 P28 118.6(5) . . n C33 O32 P28 119.4(4) . . n O35 P34 O38 116.3(3) . . n O35 P34 O36 113.8(3) . . n O38 P34 O36 101.3(3) . . n O35 P34 C22 116.1(3) . . n O38 P34 C22 101.8(3) . . n O36 P34 C22 105.9(3) . . n C37 O36 P34 118.8(4) . . n C39 O38 P34 120.5(5) . . n C41 C67 C66 121.1(7) . . n C65 C66 C67 119.5(7) . . n C64 C65 C66 120.3(7) . . n C65 C64 C63 120.9(7) . . n C64 C63 C41 118.3(6) . . n C64 C63 C62 120.1(6) . . n C41 C63 C62 121.5(6) . . n N61 C62 C63 115.6(5) . . n N61 C62 P74 105.6(4) . . n C63 C62 P74 113.1(4) . . n C60 N61 C62 110.4(5) . . n N61 C60 C59 110.4(5) . . n C60 C59 C58 113.3(5) . . n C59 C58 C57 114.0(5) . . n N56 C57 C58 111.6(6) . . n C57 N56 C55 113.9(5) . . n N56 C55 C54 115.5(5) . . n N56 C55 P68 105.4(4) . . n C54 C55 P68 113.3(4) . . n C49 C54 C53 118.9(6) . . n C49 C54 C55 120.2(6) . . n C53 C54 C55 121.0(6) . . n C52 C53 C54 119.9(6) . . n C51 C52 C53 120.0(7) . . n C50 C51 C52 121.2(7) . . n C51 C50 C49 119.6(7) . . n O48 C49 C54 116.0(6) . . n O48 C49 C50 123.5(7) . . n C54 C49 C50 120.4(7) . . n C49 O48 C47 118.3(6) . . n O48 C47 C46 108.7(6) . . n O45 C46 C47 112.2(6) . . n C46 O45 C44 110.2(5) . . n O45 C44 C43 110.8(6) . . n O42 C43 C44 111.0(6) . . n C41 O42 C43 116.4(5) . . n O42 C41 C67 124.3(7) . . n O42 C41 C63 115.9(6) . . n C67 C41 C63 119.8(7) . . n O69 P68 O70 116.1(3) . . n O69 P68 O72 113.5(3) . . n O70 P68 O72 101.2(3) . . n O69 P68 C55 115.5(3) . . n O70 P68 C55 102.7(3) . . n O72 P68 C55 106.2(3) . . n C71 O70 P68 118.1(4) . . n C73 O72 P68 121.0(5) . . n O75 P74 O76 113.3(3) . . n O75 P74 O78 115.9(3) . . n O76 P74 O78 101.9(3) . . n O75 P74 C62 116.8(3) . . n O76 P74 C62 106.4(3) . . n O78 P74 C62 100.7(3) . . n C77 O76 P74 119.3(4) . . n C79 O78 P74 119.4(4) . . n C82 O81 C85 108.5(6) . . n O81 C82 C83 107.2(7) . . n C82 C83 C84 102.6(7) . . n C83 C84 C85 102.3(7) . . n O81 C85 C84 106.2(6) . . n C92 O91 C95 103.6(8) . . n O91 C92 C93 105.9(9) . . n C94 C93 C92 106.2(9) . . n C93 C94 C95 103.9(9) . . n O91 C95 C94 104.3(10) . . n _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.728 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.143