# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Mezei, Gellert' _publ_contact_author_email gellert.mezei@wmich.edu _publ_section_title ; Single-color pseudorotaxane-based temperature sensing ; loop_ _publ_author_name G.Mezei I.Fernando S.Bairu G.Ramakrishna # Attachment '- CIF files - Gellert Mezei - new.txt' data_C4BP/BPP34C10 _database_code_depnum_ccdc_archive 'CCDC 780506' #TrackingRef '- CIF files - Gellert Mezei - new.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H70 F12 N2 O14 P2' _chemical_formula_weight 1213.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5908(2) _cell_length_b 11.5200(3) _cell_length_c 13.0613(5) _cell_angle_alpha 102.140(2) _cell_angle_beta 101.609(2) _cell_angle_gamma 109.6200(10) _cell_volume 1402.07(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9278 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 78662 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 30.55 _reflns_number_total 8541 _reflns_number_gt 7109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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_number_reflns 8541 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.271 _refine_ls_restrained_S_all 1.271 _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 P1 P 0.18903(3) 0.12572(3) 0.23908(3) 0.02096(10) Uani 1 1 d . . . F1 F 0.14084(8) 0.24351(7) 0.23489(7) 0.02637(18) Uani 1 1 d . . . F2 F 0.14736(14) 0.12446(14) 0.34963(10) 0.0591(3) Uani 1 1 d . . . F3 F 0.23791(11) 0.00993(10) 0.24229(10) 0.0469(3) Uani 1 1 d . . . F4 F 0.23179(12) 0.13306(12) 0.12957(8) 0.0480(3) Uani 1 1 d . . . F5 F 0.34332(10) 0.22550(10) 0.30884(9) 0.0458(3) Uani 1 1 d . . . F6 F 0.03421(10) 0.02710(9) 0.16795(11) 0.0532(3) Uani 1 1 d . . . O3 O 0.38333(10) 0.57394(9) 0.86807(7) 0.0224(2) Uani 1 1 d . . . O4 O 0.36649(9) 0.51747(8) 0.63332(7) 0.01893(18) Uani 1 1 d . . . O5 O 0.28606(9) 0.63000(8) 0.46889(7) 0.01873(18) Uani 1 1 d . . . O6 O 0.58485(10) 0.87092(9) 1.30315(7) 0.0233(2) Uani 1 1 d . . . O7 O 0.69358(9) 1.10663(8) 1.46668(7) 0.01982(19) Uani 1 1 d . . . C12 C 0.47396(13) 0.53183(12) 0.81552(10) 0.0195(2) Uani 1 1 d . . . H12A H 0.5168 0.4877 0.8578 0.023 Uiso 1 1 calc R . . H12B H 0.5480 0.6056 0.8102 0.023 Uiso 1 1 calc R . . C13 C 0.38698(13) 0.44150(11) 0.70285(10) 0.0184(2) Uani 1 1 d . . . H13A H 0.4349 0.3891 0.6751 0.022 Uiso 1 1 calc R . . H13B H 0.2972 0.3844 0.7056 0.022 Uiso 1 1 calc R . . C14 C 0.28807(13) 0.44237(11) 0.52297(10) 0.0190(2) Uani 1 1 d . . . H14A H 0.1884 0.4154 0.5143 0.023 Uiso 1 1 calc R . . H14B H 0.3080 0.3658 0.5034 0.023 Uiso 1 1 calc R . . C15 C 0.32963(14) 0.52459(12) 0.45073(10) 0.0210(2) Uani 1 1 d . . . H15A H 0.4307 0.5580 0.4654 0.025 Uiso 1 1 calc R . . H15B H 0.2873 0.4722 0.3746 0.025 Uiso 1 1 calc R . . C16 C 0.37298(14) 0.73274(12) 0.43843(11) 0.0227(3) Uani 1 1 d . . . H16A H 0.3858 0.6979 0.3687 0.027 Uiso 1 1 calc R . . H16B H 0.4644 0.7746 0.4928 0.027 Uiso 1 1 calc R . . C17 C 0.68897(14) 1.16934(12) 1.57112(10) 0.0212(2) Uani 1 1 d . . . H17A H 0.7831 1.2116 1.6217 0.025 Uiso 1 1 calc R . . H17B H 0.6327 1.1059 1.5997 0.025 Uiso 1 1 calc R . . C18 C 0.74639(14) 1.00906(12) 1.47376(10) 0.0225(3) Uani 1 1 d . . . H18A H 0.6942 0.9517 1.5091 0.027 Uiso 1 1 calc R . . H18B H 0.8443 1.0483 1.5170 0.027 Uiso 1 1 calc R . . C19 C 0.73134(14) 0.93425(12) 1.35977(11) 0.0226(2) Uani 1 1 d . . . H19A H 0.7784 0.9921 1.3225 0.027 Uiso 1 1 calc R . . H19B H 0.7728 0.8712 1.3624 0.027 Uiso 1 1 calc R . . C20 C 0.54562(13) 0.80040(11) 1.19489(10) 0.0194(2) Uani 1 1 d . . . C21 C 0.63815(14) 0.78539(12) 1.13681(10) 0.0210(2) Uani 1 1 d . . . H21 H 0.7343 0.8254 1.1711 0.025 Uiso 1 1 calc R . . C22 C 0.58693(13) 0.71008(12) 1.02658(10) 0.0210(2) Uani 1 1 d . . . H22 H 0.6493 0.7009 0.9877 0.025 Uiso 1 1 calc R . . C23 C 0.44393(13) 0.64930(12) 0.97544(10) 0.0192(2) Uani 1 1 d . . . C24 C 0.35060(14) 0.66456(13) 1.03394(10) 0.0215(2) Uani 1 1 d . . . H24 H 0.2544 0.6235 0.9999 0.026 Uiso 1 1 calc R . . C25 C 0.40105(14) 0.74081(12) 1.14270(10) 0.0213(2) Uani 1 1 d . . . H25 H 0.3387 0.7522 1.1808 0.026 Uiso 1 1 calc R . . C9 C 0.44287(11) 0.95874(10) 0.94872(9) 0.0156(2) Uani 1 1 d . . . C7 C 0.36154(13) 0.81998(13) 0.76225(10) 0.0229(3) Uani 1 1 d . . . H7 H 0.3804 0.7786 0.7015 0.028 Uiso 1 1 calc R . . C10 C 0.30351(12) 0.94017(12) 0.94102(10) 0.0202(2) Uani 1 1 d . . . H10 H 0.2814 0.9799 1.0005 0.024 Uiso 1 1 calc R . . C8 C 0.46976(13) 0.89726(13) 0.85619(10) 0.0227(3) Uani 1 1 d . . . H8 H 0.5615 0.9086 0.8581 0.027 Uiso 1 1 calc R . . O1 O 0.01630(11) 0.39593(9) 0.85466(8) 0.0267(2) Uani 1 1 d . . . O2 O 0.05005(11) 0.33858(9) 0.69043(9) 0.0292(2) Uani 1 1 d . . . N1 N 0.22860(10) 0.80427(10) 0.75815(8) 0.0177(2) Uani 1 1 d . . . C5 C 0.08003(13) 0.57600(12) 0.65721(10) 0.0211(2) Uani 1 1 d . . . H5A H 0.1631 0.5583 0.6559 0.025 Uiso 1 1 calc R . . H5B H 0.0066 0.5193 0.5903 0.025 Uiso 1 1 calc R . . C6 C 0.11228(13) 0.71498(12) 0.65814(10) 0.0206(2) Uani 1 1 d . . . H6A H 0.1390 0.7278 0.5933 0.025 Uiso 1 1 calc R . . H6B H 0.0293 0.7335 0.6571 0.025 Uiso 1 1 calc R . . C4 C 0.03395(13) 0.54376(12) 0.75431(10) 0.0207(2) Uani 1 1 d . . . H4A H 0.0968 0.6104 0.8215 0.025 Uiso 1 1 calc R . . H4B H -0.0598 0.5417 0.7472 0.025 Uiso 1 1 calc R . . C3 C 0.03459(13) 0.41472(12) 0.76029(10) 0.0216(2) Uani 1 1 d . . . C2 C 0.02884(18) 0.27875(15) 0.87207(13) 0.0326(3) Uani 1 1 d . . . H2A H 0.1196 0.2792 0.8686 0.039 Uiso 1 1 calc R . . H2B H -0.0436 0.2030 0.8160 0.039 Uiso 1 1 calc R . . C1 C 0.0131(2) 0.27611(19) 0.98250(15) 0.0444(4) Uani 1 1 d . . . H1A H 0.0798 0.3550 1.0365 0.067 Uiso 1 1 calc R . . H1B H 0.0293 0.2042 0.9992 0.067 Uiso 1 1 calc R . . H1C H -0.0802 0.2675 0.9829 0.067 Uiso 1 1 calc R . . C11 C 0.19926(13) 0.86308(12) 0.84537(11) 0.0207(2) Uani 1 1 d . . . H11 H 0.1068 0.8513 0.8408 0.025 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 P1 0.01856(16) 0.02266(17) 0.02430(18) 0.00714(13) 0.00662(13) 0.01109(13) F1 0.0241(4) 0.0218(4) 0.0345(4) 0.0061(3) 0.0079(3) 0.0125(3) F2 0.0773(9) 0.0909(9) 0.0554(7) 0.0529(7) 0.0453(7) 0.0556(8) F3 0.0334(5) 0.0332(5) 0.0814(8) 0.0212(5) 0.0119(5) 0.0225(4) F4 0.0576(6) 0.0832(8) 0.0331(5) 0.0236(5) 0.0278(5) 0.0519(6) F5 0.0249(4) 0.0416(5) 0.0538(6) 0.0007(5) -0.0082(4) 0.0122(4) F6 0.0220(4) 0.0231(4) 0.0927(9) -0.0047(5) -0.0052(5) 0.0088(4) O3 0.0242(4) 0.0315(5) 0.0144(4) 0.0039(3) 0.0058(3) 0.0164(4) O4 0.0247(4) 0.0168(4) 0.0133(4) 0.0043(3) 0.0016(3) 0.0083(3) O5 0.0205(4) 0.0189(4) 0.0211(4) 0.0079(3) 0.0093(3) 0.0102(3) O6 0.0245(4) 0.0248(4) 0.0179(4) 0.0019(3) 0.0070(3) 0.0090(4) O7 0.0272(4) 0.0187(4) 0.0161(4) 0.0057(3) 0.0067(3) 0.0116(3) C12 0.0219(5) 0.0248(6) 0.0163(5) 0.0066(4) 0.0062(4) 0.0139(5) C13 0.0234(5) 0.0186(5) 0.0179(5) 0.0078(4) 0.0079(4) 0.0116(4) C14 0.0211(5) 0.0181(5) 0.0163(5) 0.0029(4) 0.0031(4) 0.0087(4) C15 0.0270(6) 0.0244(6) 0.0162(5) 0.0063(4) 0.0077(4) 0.0148(5) C16 0.0258(6) 0.0224(6) 0.0248(6) 0.0096(5) 0.0138(5) 0.0103(5) C17 0.0276(6) 0.0209(6) 0.0161(5) 0.0056(4) 0.0078(4) 0.0099(5) C18 0.0286(6) 0.0188(5) 0.0209(6) 0.0060(4) 0.0047(5) 0.0120(5) C19 0.0249(6) 0.0203(6) 0.0233(6) 0.0058(4) 0.0063(5) 0.0109(5) C20 0.0262(6) 0.0180(5) 0.0173(5) 0.0061(4) 0.0077(4) 0.0114(5) C21 0.0232(6) 0.0199(5) 0.0209(6) 0.0057(4) 0.0067(4) 0.0099(5) C22 0.0246(6) 0.0233(6) 0.0195(6) 0.0063(4) 0.0092(5) 0.0132(5) C23 0.0253(6) 0.0215(5) 0.0158(5) 0.0076(4) 0.0064(4) 0.0141(5) C24 0.0234(6) 0.0279(6) 0.0172(5) 0.0076(4) 0.0061(4) 0.0145(5) C25 0.0244(6) 0.0266(6) 0.0182(5) 0.0077(4) 0.0091(4) 0.0141(5) C9 0.0140(5) 0.0152(5) 0.0198(5) 0.0078(4) 0.0058(4) 0.0066(4) C7 0.0179(5) 0.0319(6) 0.0205(6) 0.0075(5) 0.0082(4) 0.0103(5) C10 0.0162(5) 0.0203(5) 0.0237(6) 0.0031(4) 0.0066(4) 0.0085(4) C8 0.0157(5) 0.0331(7) 0.0208(6) 0.0075(5) 0.0074(4) 0.0106(5) O1 0.0350(5) 0.0236(5) 0.0264(5) 0.0101(4) 0.0122(4) 0.0141(4) O2 0.0310(5) 0.0232(5) 0.0311(5) 0.0032(4) 0.0121(4) 0.0091(4) N1 0.0154(4) 0.0212(5) 0.0180(5) 0.0080(4) 0.0055(4) 0.0074(4) C5 0.0206(5) 0.0240(6) 0.0164(5) 0.0027(4) 0.0056(4) 0.0081(4) C6 0.0176(5) 0.0280(6) 0.0147(5) 0.0069(4) 0.0038(4) 0.0077(5) C4 0.0237(6) 0.0217(6) 0.0174(5) 0.0051(4) 0.0064(4) 0.0099(5) C3 0.0176(5) 0.0222(6) 0.0204(6) 0.0046(4) 0.0025(4) 0.0054(4) C2 0.0450(8) 0.0306(7) 0.0350(8) 0.0161(6) 0.0182(7) 0.0228(6) C1 0.0718(13) 0.0488(10) 0.0390(9) 0.0273(8) 0.0291(9) 0.0396(9) C11 0.0147(5) 0.0222(6) 0.0254(6) 0.0053(4) 0.0066(4) 0.0085(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 P1 F5 1.5876(9) . ? P1 F3 1.5898(9) . ? P1 F6 1.5920(9) . ? P1 F2 1.5940(11) . ? P1 F4 1.5949(10) . ? P1 F1 1.6093(8) . ? O3 C23 1.3725(14) . ? O3 C12 1.4372(14) . ? O4 C13 1.4213(14) . ? O4 C14 1.4237(13) . ? O5 C16 1.4214(15) . ? O5 C15 1.4294(14) . ? O6 C20 1.3732(14) . ? O6 C19 1.4274(16) . ? O7 C17 1.4217(14) . ? O7 C18 1.4247(14) . ? C12 C13 1.5045(16) . ? C14 C15 1.4980(18) . ? C16 C17 1.4972(17) 2_677 ? C17 C16 1.4972(17) 2_677 ? C18 C19 1.5024(17) . ? C20 C21 1.3870(17) . ? C20 C25 1.3990(18) . ? C21 C22 1.4015(16) . ? C22 C23 1.3836(17) . ? C23 C24 1.3985(17) . ? C24 C25 1.3890(16) . ? C9 C10 1.3976(15) . ? C9 C8 1.3990(16) . ? C9 C9 1.484(2) 2_677 ? C7 N1 1.3463(15) . ? C7 C8 1.3788(17) . ? C10 C11 1.3741(16) . ? O1 C3 1.3356(16) . ? O1 C2 1.4591(17) . ? O2 C3 1.2036(15) . ? N1 C11 1.3463(15) . ? N1 C6 1.4893(15) . ? C5 C6 1.5176(18) . ? C5 C4 1.5199(18) . ? C4 C3 1.5071(18) . ? C2 C1 1.490(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F5 P1 F3 89.55(5) . . ? F5 P1 F6 179.11(7) . . ? F3 P1 F6 91.11(5) . . ? F5 P1 F2 89.63(7) . . ? F3 P1 F2 91.93(7) . . ? F6 P1 F2 90.94(7) . . ? F5 P1 F4 89.34(7) . . ? F3 P1 F4 90.16(6) . . ? F6 P1 F4 90.07(7) . . ? F2 P1 F4 177.66(7) . . ? F5 P1 F1 90.15(5) . . ? F3 P1 F1 179.27(6) . . ? F6 P1 F1 89.17(5) . . ? F2 P1 F1 88.74(6) . . ? F4 P1 F1 89.17(5) . . ? C23 O3 C12 115.74(9) . . ? C13 O4 C14 113.24(9) . . ? C16 O5 C15 109.79(9) . . ? C20 O6 C19 117.71(10) . . ? C17 O7 C18 110.57(9) . . ? O3 C12 C13 108.12(10) . . ? O4 C13 C12 107.98(9) . . ? O4 C14 C15 107.81(10) . . ? O5 C15 C14 111.24(10) . . ? O5 C16 C17 111.76(10) . 2_677 ? O7 C17 C16 110.02(10) . 2_677 ? O7 C18 C19 108.49(10) . . ? O6 C19 C18 107.31(10) . . ? O6 C20 C21 124.67(12) . . ? O6 C20 C25 115.63(11) . . ? C21 C20 C25 119.69(11) . . ? C20 C21 C22 120.11(12) . . ? C23 C22 C21 120.23(11) . . ? O3 C23 C22 124.74(11) . . ? O3 C23 C24 115.59(11) . . ? C22 C23 C24 119.67(11) . . ? C25 C24 C23 120.24(12) . . ? C24 C25 C20 120.04(11) . . ? C10 C9 C8 117.42(11) . . ? C10 C9 C9 120.84(13) . 2_677 ? C8 C9 C9 121.74(13) . 2_677 ? N1 C7 C8 120.18(11) . . ? C11 C10 C9 119.90(11) . . ? C7 C8 C9 120.61(11) . . ? C3 O1 C2 114.39(10) . . ? C7 N1 C11 120.71(11) . . ? C7 N1 C6 119.42(10) . . ? C11 N1 C6 119.78(10) . . ? C6 C5 C4 114.40(10) . . ? N1 C6 C5 109.86(10) . . ? C3 C4 C5 110.81(10) . . ? O2 C3 O1 124.13(13) . . ? O2 C3 C4 125.18(12) . . ? O1 C3 C4 110.68(10) . . ? O1 C2 C1 107.45(12) . . ? N1 C11 C10 121.17(11) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.882 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.058 #===END data_C4BP _database_code_depnum_ccdc_archive 'CCDC 780507' #TrackingRef '- CIF files - Gellert Mezei - new.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 F12 N2 O4 P2' _chemical_formula_weight 676.42 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 Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' 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' '-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 12.7649(2) _cell_length_b 14.3247(2) _cell_length_c 15.5038(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2834.92(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6205 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 21.96 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9060 _exptl_absorpt_correction_T_max 0.9613 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 45964 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 30.55 _reflns_number_total 4333 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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_number_reflns 4333 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1419 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.3066 _refine_ls_wR_factor_gt 0.2767 _refine_ls_goodness_of_fit_ref 1.742 _refine_ls_restrained_S_all 1.742 _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 P1 P 0.72613(8) 0.10657(8) 0.38067(7) 0.0573(4) Uani 1 1 d . . . F1 F 0.6262(4) 0.0462(4) 0.3963(3) 0.176(2) Uani 1 1 d . . . F2 F 0.6755(3) 0.1802(2) 0.4418(2) 0.1237(14) Uani 1 1 d . . . F3 F 0.8180(5) 0.1693(5) 0.3630(4) 0.239(3) Uani 1 1 d . . . F4 F 0.7723(4) 0.0302(3) 0.3224(3) 0.181(2) Uani 1 1 d . . . F5 F 0.7802(3) 0.0635(3) 0.4608(2) 0.1407(17) Uani 1 1 d . . . F6 F 0.6646(3) 0.1461(2) 0.29952(19) 0.1172(12) Uani 1 1 d . . . O1 O 0.15595(19) 0.28203(17) 0.88658(16) 0.0528(7) Uani 1 1 d . . . O2 O 0.31877(19) 0.24081(19) 0.8511(2) 0.0621(8) Uani 1 1 d . . . N1 N 0.00122(19) 0.10703(17) 0.70351(17) 0.0391(6) Uani 1 1 d . . . C1 C 0.0493(3) 0.1472(2) 0.6368(2) 0.0479(8) Uani 1 1 d . . . H1 H 0.0831 0.2040 0.6448 0.058 Uiso 1 1 calc R . . C2 C 0.0501(3) 0.1070(2) 0.5575(2) 0.0444(8) Uani 1 1 d . . . H2 H 0.0848 0.1366 0.5124 0.053 Uiso 1 1 calc R . . C3 C 0.0002(2) 0.02253(19) 0.54265(19) 0.0352(7) Uani 1 1 d . . . C4 C -0.0478(3) -0.0185(2) 0.6140(2) 0.0470(8) Uani 1 1 d . . . H4 H -0.0805 -0.0762 0.6084 0.056 Uiso 1 1 calc R . . C5 C -0.0470(3) 0.0253(2) 0.6919(2) 0.0499(8) Uani 1 1 d . . . H5 H -0.0811 -0.0024 0.7383 0.060 Uiso 1 1 calc R . . C6 C -0.0011(3) 0.1515(3) 0.7900(2) 0.0509(9) Uani 1 1 d . . . H6A H -0.0717 0.1483 0.8130 0.061 Uiso 1 1 calc R . . H6B H 0.0176 0.2169 0.7844 0.061 Uiso 1 1 calc R . . C7 C 0.0737(3) 0.1046(3) 0.8524(2) 0.0548(9) Uani 1 1 d . . . H7A H 0.0555 0.1236 0.9105 0.066 Uiso 1 1 calc R . . H7B H 0.0639 0.0376 0.8486 0.066 Uiso 1 1 calc R . . C8 C 0.1881(3) 0.1264(2) 0.8371(2) 0.0506(9) Uani 1 1 d . . . H8A H 0.2306 0.0835 0.8706 0.061 Uiso 1 1 calc R . . H8B H 0.2042 0.1164 0.7767 0.061 Uiso 1 1 calc R . . C9 C 0.2169(3) 0.2252(2) 0.8611(2) 0.0441(8) Uani 1 1 d . . . C10 C 0.3566(4) 0.3340(3) 0.8730(3) 0.0730(13) Uani 1 1 d . . . H10A H 0.3050 0.3798 0.8553 0.088 Uiso 1 1 calc R . . H10B H 0.4207 0.3463 0.8413 0.088 Uiso 1 1 calc R . . C11 C 0.3769(4) 0.3442(3) 0.9659(3) 0.0928(17) Uani 1 1 d . . . H11A H 0.3121 0.3394 0.9970 0.139 Uiso 1 1 calc R . . H11B H 0.4081 0.4040 0.9768 0.139 Uiso 1 1 calc R . . H11C H 0.4237 0.2958 0.9846 0.139 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 P1 0.0620(7) 0.0625(7) 0.0475(6) -0.0094(5) -0.0074(5) 0.0144(5) F1 0.163(4) 0.209(5) 0.157(4) 0.045(3) -0.034(3) -0.099(4) F2 0.170(3) 0.129(3) 0.072(2) -0.0244(19) -0.006(2) 0.085(2) F3 0.233(5) 0.304(7) 0.179(5) -0.044(4) 0.052(4) -0.200(6) F4 0.239(5) 0.196(4) 0.108(3) -0.079(3) -0.048(3) 0.150(4) F5 0.145(3) 0.201(4) 0.076(2) -0.024(2) -0.042(2) 0.104(3) F6 0.161(3) 0.124(2) 0.066(2) 0.0142(18) -0.0238(19) 0.051(2) O1 0.0594(14) 0.0462(13) 0.0529(16) -0.0095(11) -0.0019(11) 0.0149(11) O2 0.0489(14) 0.0645(17) 0.073(2) -0.0172(14) -0.0027(13) 0.0066(12) N1 0.0389(13) 0.0401(14) 0.0383(15) -0.0015(11) -0.0040(11) 0.0011(10) C1 0.0554(19) 0.0414(17) 0.047(2) 0.0015(15) -0.0001(16) -0.0084(15) C2 0.0557(18) 0.0384(16) 0.0392(18) 0.0026(14) 0.0038(15) -0.0126(13) C3 0.0325(13) 0.0364(15) 0.0366(16) 0.0050(12) -0.0030(12) 0.0014(11) C4 0.0540(18) 0.0451(17) 0.042(2) 0.0000(15) 0.0038(15) -0.0182(15) C5 0.0575(19) 0.053(2) 0.0394(19) 0.0048(16) 0.0070(16) -0.0137(16) C6 0.0549(19) 0.056(2) 0.042(2) -0.0108(16) -0.0001(16) 0.0028(16) C7 0.065(2) 0.058(2) 0.042(2) -0.0010(17) -0.0084(18) -0.0050(17) C8 0.0557(19) 0.051(2) 0.045(2) -0.0097(16) -0.0082(17) 0.0112(16) C9 0.0520(19) 0.0483(18) 0.0319(17) -0.0055(14) -0.0055(14) 0.0075(15) C10 0.067(3) 0.064(3) 0.088(4) -0.005(2) -0.001(2) -0.014(2) C11 0.109(4) 0.071(3) 0.099(4) -0.019(3) -0.030(3) -0.013(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 F3 1.503(4) . ? P1 F4 1.536(3) . ? P1 F5 1.550(3) . ? P1 F2 1.559(3) . ? P1 F1 1.560(4) . ? P1 F6 1.588(3) . ? O1 C9 1.194(4) . ? O2 C9 1.328(4) . ? O2 C10 1.459(5) . ? N1 C1 1.333(4) . ? N1 C5 1.334(4) . ? N1 C6 1.485(4) . ? C1 C2 1.357(5) . ? C2 C3 1.387(4) . ? C3 C4 1.395(4) . ? C3 C3 1.472(6) 5_556 ? C4 C5 1.360(5) . ? C6 C7 1.516(5) . ? C7 C8 1.512(5) . ? C8 C9 1.509(5) . ? C10 C11 1.471(7) . ? 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 F3 P1 F4 91.1(4) . . ? F3 P1 F5 92.1(3) . . ? F4 P1 F5 91.0(2) . . ? F3 P1 F2 91.7(3) . . ? F4 P1 F2 177.1(3) . . ? F5 P1 F2 88.10(17) . . ? F3 P1 F1 176.4(4) . . ? F4 P1 F1 90.6(3) . . ? F5 P1 F1 91.1(3) . . ? F2 P1 F1 86.7(3) . . ? F3 P1 F6 91.7(3) . . ? F4 P1 F6 88.75(19) . . ? F5 P1 F6 176.3(2) . . ? F2 P1 F6 92.02(17) . . ? F1 P1 F6 85.2(2) . . ? C9 O2 C10 116.8(3) . . ? C1 N1 C5 119.0(3) . . ? C1 N1 C6 121.6(3) . . ? C5 N1 C6 119.3(3) . . ? N1 C1 C2 121.5(3) . . ? C1 C2 C3 121.1(3) . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C3 122.2(3) . 5_556 ? C4 C3 C3 121.8(3) . 5_556 ? C5 C4 C3 120.4(3) . . ? N1 C5 C4 121.9(3) . . ? N1 C6 C7 111.9(3) . . ? C8 C7 C6 114.7(3) . . ? C9 C8 C7 113.0(3) . . ? O1 C9 O2 124.2(3) . . ? O1 C9 C8 124.2(3) . . ? O2 C9 C8 111.6(3) . . ? O2 C10 C11 112.1(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.718 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.084 #===END data_BN32C8 _database_code_depnum_ccdc_archive 'CCDC 780508' #TrackingRef '- CIF files - Gellert Mezei - new.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 O8' _chemical_formula_weight 548.61 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4523(3) _cell_length_b 8.8380(3) _cell_length_c 10.7212(5) _cell_angle_alpha 84.569(2) _cell_angle_beta 77.234(2) _cell_angle_gamma 83.613(2) _cell_volume 682.61(5) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4908 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9277 _exptl_absorpt_correction_T_max 0.9450 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9470 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.06 _reflns_number_total 3269 _reflns_number_gt 2461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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_number_reflns 3269 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1617 _refine_ls_wR_factor_gt 0.1458 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 1.03738(11) -0.14061(9) 0.88826(8) 0.0504(3) Uani 1 1 d . . . O2 O 1.24824(12) -0.41710(9) 0.94789(8) 0.0544(3) Uani 1 1 d . . . O3 O 0.56302(15) 0.39573(13) 0.32878(9) 0.0801(4) Uani 1 1 d . . . O4 O 0.80558(12) 0.32101(12) 0.49744(9) 0.0616(3) Uani 1 1 d . . . C1 C 0.91017(16) -0.05517(13) 0.82987(11) 0.0436(3) Uani 1 1 d . . . C2 C 0.72273(17) -0.05521(15) 0.87252(12) 0.0526(3) Uani 1 1 d . . . H2 H 0.6748 -0.1181 0.9439 0.063 Uiso 1 1 calc R . . C3 C 0.60338(17) 0.03995(16) 0.80814(13) 0.0552(3) Uani 1 1 d . . . H3 H 0.4764 0.0387 0.8373 0.066 Uiso 1 1 calc R . . C4 C 0.66911(16) 0.13375(15) 0.70424(12) 0.0503(3) Uani 1 1 d . . . H4 H 0.5877 0.1977 0.6642 0.060 Uiso 1 1 calc R . . C5 C 0.93589(17) 0.22771(14) 0.54603(11) 0.0474(3) Uani 1 1 d . . . C6 C 1.12219(18) 0.21969(15) 0.49747(13) 0.0551(3) Uani 1 1 d . . . H6 H 1.1693 0.2797 0.4240 0.066 Uiso 1 1 calc R . . C7 C 1.24194(17) 0.12110(15) 0.55843(13) 0.0545(3) Uani 1 1 d . . . H7 H 1.3684 0.1166 0.5244 0.065 Uiso 1 1 calc R . . C8 C 1.17848(16) 0.03196(14) 0.66573(12) 0.0481(3) Uani 1 1 d . . . H8 H 1.2609 -0.0321 0.7048 0.058 Uiso 1 1 calc R . . C9 C 0.98600(15) 0.03671(12) 0.71810(10) 0.0409(3) Uani 1 1 d . . . C10 C 0.86179(15) 0.13377(13) 0.65713(11) 0.0422(3) Uani 1 1 d . . . C11 C 0.96920(18) -0.24516(15) 0.99362(12) 0.0530(3) Uani 1 1 d . . . H11A H 0.8994 -0.3173 0.9662 0.064 Uiso 1 1 calc R . . H11B H 0.8879 -0.1902 1.0616 0.064 Uiso 1 1 calc R . . C12 C 1.1291(2) -0.32804(15) 1.04159(12) 0.0566(3) Uani 1 1 d . . . H12A H 1.1989 -0.2546 1.0673 0.068 Uiso 1 1 calc R . . H12B H 1.0832 -0.3942 1.1167 0.068 Uiso 1 1 calc R . . C13 C 1.41500(19) -0.35165(16) 0.89259(14) 0.0590(4) Uani 1 1 d . . . H13A H 1.4917 -0.3577 0.9555 0.071 Uiso 1 1 calc R . . H13B H 1.3880 -0.2448 0.8669 0.071 Uiso 1 1 calc R . . C14 C 0.8600(2) 0.40301(16) 0.37644(13) 0.0583(4) Uani 1 1 d . . . H14A H 0.9119 0.3327 0.3108 0.070 Uiso 1 1 calc R . . H14B H 0.9527 0.4703 0.3802 0.070 Uiso 1 1 calc R . . C15 C 0.6921(2) 0.49361(17) 0.34603(14) 0.0638(4) Uani 1 1 d . . . H15A H 0.6360 0.5580 0.4154 0.077 Uiso 1 1 calc R . . H15B H 0.7269 0.5591 0.2685 0.077 Uiso 1 1 calc R . . C16 C 0.4842(2) 0.4330(2) 0.22062(14) 0.0691(4) Uani 1 1 d . . . H16A H 0.4833 0.5421 0.1991 0.083 Uiso 1 1 calc R . . H16B H 0.3571 0.4079 0.2418 0.083 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 O1 0.0495(5) 0.0461(5) 0.0550(5) 0.0078(4) -0.0155(4) -0.0025(4) O2 0.0557(5) 0.0419(5) 0.0615(6) -0.0004(4) -0.0041(4) -0.0065(4) O3 0.0960(8) 0.0901(8) 0.0572(6) 0.0267(5) -0.0278(6) -0.0254(7) O4 0.0583(6) 0.0682(6) 0.0489(5) 0.0125(4) -0.0075(4) 0.0125(5) C1 0.0452(6) 0.0397(6) 0.0476(6) -0.0033(5) -0.0140(5) -0.0030(5) C2 0.0494(7) 0.0540(7) 0.0533(7) 0.0027(6) -0.0084(6) -0.0101(5) C3 0.0394(6) 0.0650(8) 0.0607(8) -0.0050(6) -0.0089(6) -0.0055(6) C4 0.0432(6) 0.0551(7) 0.0531(7) -0.0052(5) -0.0144(5) 0.0027(5) C5 0.0506(7) 0.0458(7) 0.0446(6) -0.0036(5) -0.0108(5) 0.0030(5) C6 0.0548(7) 0.0564(8) 0.0492(7) 0.0028(6) -0.0034(6) -0.0051(6) C7 0.0410(6) 0.0610(8) 0.0587(8) -0.0033(6) -0.0052(6) -0.0051(5) C8 0.0406(6) 0.0501(7) 0.0543(7) -0.0031(5) -0.0140(5) -0.0005(5) C9 0.0421(6) 0.0382(6) 0.0440(6) -0.0053(5) -0.0122(5) -0.0029(5) C10 0.0432(6) 0.0421(6) 0.0423(6) -0.0058(5) -0.0118(5) -0.0006(5) C11 0.0604(8) 0.0465(7) 0.0480(7) 0.0022(5) -0.0061(6) -0.0024(6) C12 0.0700(8) 0.0500(7) 0.0462(7) 0.0027(5) -0.0109(6) 0.0025(6) C13 0.0556(7) 0.0590(8) 0.0640(8) 0.0126(6) -0.0191(6) -0.0139(6) C14 0.0691(8) 0.0541(7) 0.0469(7) 0.0027(5) -0.0087(6) 0.0017(6) C15 0.0772(9) 0.0572(8) 0.0550(8) 0.0086(6) -0.0179(7) -0.0005(7) C16 0.0514(7) 0.0907(11) 0.0594(8) 0.0172(7) -0.0122(6) -0.0002(7) _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 C1 1.3691(13) . ? O1 C11 1.4286(14) . ? O2 C13 1.4141(16) . ? O2 C12 1.4202(15) . ? O3 C16 1.4083(17) . ? O3 C15 1.4150(18) . ? O4 C5 1.3632(14) . ? O4 C14 1.4239(16) . ? C1 C2 1.3704(17) . ? C1 C9 1.4259(16) . ? C2 C3 1.4034(18) . ? C3 C4 1.3574(18) . ? C4 C10 1.4130(17) . ? C5 C6 1.3672(18) . ? C5 C10 1.4272(17) . ? C6 C7 1.3999(18) . ? C7 C8 1.3560(18) . ? C8 C9 1.4177(16) . ? C9 C10 1.4158(16) . ? C11 C12 1.4920(19) . ? C13 C16 1.482(2) 2_756 ? C14 C15 1.4900(19) . ? C16 C13 1.482(2) 2_756 ? 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 O1 C11 117.37(9) . . ? C13 O2 C12 113.13(10) . . ? C16 O3 C15 116.07(12) . . ? C5 O4 C14 118.75(10) . . ? O1 C1 C2 124.05(11) . . ? O1 C1 C9 115.11(10) . . ? C2 C1 C9 120.83(11) . . ? C1 C2 C3 119.79(11) . . ? C4 C3 C2 121.51(11) . . ? C3 C4 C10 119.72(11) . . ? O4 C5 C6 125.62(12) . . ? O4 C5 C10 113.89(10) . . ? C6 C5 C10 120.49(12) . . ? C5 C6 C7 119.94(12) . . ? C8 C7 C6 121.75(11) . . ? C7 C8 C9 119.76(11) . . ? C10 C9 C8 119.58(11) . . ? C10 C9 C1 117.85(10) . . ? C8 C9 C1 122.56(10) . . ? C4 C10 C9 120.22(11) . . ? C4 C10 C5 121.31(11) . . ? C9 C10 C5 118.45(11) . . ? O1 C11 C12 108.82(11) . . ? O2 C12 C11 112.45(10) . . ? O2 C13 C16 110.34(12) . 2_756 ? O4 C14 C15 107.56(11) . . ? O3 C15 C14 110.51(12) . . ? O3 C16 C13 112.86(12) . 2_756 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.203 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.037