# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 883383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H45 N3 O11' _chemical_formula_weight 683.74 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' N N 0.0061 0.0033 '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 9.2812(5) _cell_length_b 10.8141(7) _cell_length_c 17.5421(12) _cell_angle_alpha 90.146(4) _cell_angle_beta 96.815(4) _cell_angle_gamma 99.763(3) _cell_volume 1722.44(19) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 4439 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 29.61 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9617 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 28037 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6776 _reflns_number_gt 5239 _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^)+(0.0859P)^2^+1.3565P] 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 6776 _refine_ls_number_parameters 442 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.129 _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 C1 C 0.4438(3) -0.5319(3) 0.72396(18) 0.0108(7) Uani 1 1 d . . . C2 C 0.4979(3) -0.4429(3) 0.66398(17) 0.0083(6) Uani 1 1 d . . . C3 C 0.4083(3) -0.4204(3) 0.59812(18) 0.0098(6) Uani 1 1 d . . . H3 H 0.3096 -0.4636 0.5894 0.012 Uiso 1 1 calc R . . C4 C 0.4619(3) -0.3352(3) 0.54495(18) 0.0094(6) Uani 1 1 d . . . H4 H 0.4003 -0.3210 0.4998 0.011 Uiso 1 1 calc R . . C5 C 0.6068(3) -0.2702(3) 0.55784(17) 0.0081(6) Uani 1 1 d . . . C6 C 0.6963(3) -0.2943(3) 0.62349(18) 0.0101(6) Uani 1 1 d . . . H6 H 0.7951 -0.2511 0.6324 0.012 Uiso 1 1 calc R . . C7 C 0.6436(3) -0.3802(3) 0.67580(18) 0.0102(6) Uani 1 1 d . . . H7 H 0.7065 -0.3967 0.7200 0.012 Uiso 1 1 calc R . . C8 C 0.6632(3) -0.1780(3) 0.50071(17) 0.0068(6) Uani 1 1 d . . . C9 C 0.6594(3) -0.2148(3) 0.42453(17) 0.0081(6) Uani 1 1 d . . . H9 H 0.6180 -0.2987 0.4089 0.010 Uiso 1 1 calc R . . C10 C 0.7147(3) -0.1316(3) 0.37058(18) 0.0076(6) Uani 1 1 d . . . H10 H 0.7135 -0.1599 0.3192 0.009 Uiso 1 1 calc R . . C11 C 0.7722(3) -0.0062(3) 0.39150(17) 0.0067(4) Uani 1 1 d . . . C12 C 0.7692(3) 0.0327(3) 0.46702(17) 0.0067(4) Uani 1 1 d U . . C13 C 0.7222(3) -0.0533(3) 0.52201(17) 0.0064(6) Uani 1 1 d . . . C14 C 0.6370(3) 0.0589(3) 0.62065(18) 0.0101(6) Uani 1 1 d . . . H14A H 0.5399 0.0060 0.6236 0.012 Uiso 1 1 calc R . . H14B H 0.6245 0.1249 0.5827 0.012 Uiso 1 1 calc R . . C15 C 0.6996(3) 0.1169(3) 0.69779(18) 0.0137(7) Uani 1 1 d . . . H15A H 0.6235 0.1551 0.7197 0.016 Uiso 1 1 calc R . . H15B H 0.7267 0.0506 0.7327 0.016 Uiso 1 1 calc R . . C16 C 0.7919(4) 0.3338(3) 0.6819(2) 0.0168(7) Uani 1 1 d . . . H16A H 0.7855 0.3731 0.7322 0.020 Uiso 1 1 calc R . . H16B H 0.6953 0.3286 0.6503 0.020 Uiso 1 1 calc R . . C17 C 0.9088(4) 0.4128(3) 0.64261(19) 0.0173(7) Uani 1 1 d . . . H17A H 0.9098 0.5024 0.6547 0.021 Uiso 1 1 calc R . . H17B H 1.0061 0.3926 0.6628 0.021 Uiso 1 1 calc R . . C18 C 0.9915(3) 0.3343(3) 0.5293(2) 0.0158(7) Uani 1 1 d . . . H18A H 1.0898 0.3624 0.5585 0.019 Uiso 1 1 calc R . . H18B H 0.9965 0.3613 0.4757 0.019 Uiso 1 1 calc R . . C19 C 0.9558(3) 0.1934(3) 0.53010(19) 0.0111(7) Uani 1 1 d . . . H19A H 1.0297 0.1560 0.5057 0.013 Uiso 1 1 calc R . . H19B H 0.9557 0.1641 0.5835 0.013 Uiso 1 1 calc R . . C20 C 0.8390(3) 0.0804(3) 0.33442(17) 0.0081(6) Uani 1 1 d . . . C21 C 0.9326(3) 0.0385(3) 0.28712(17) 0.0093(6) Uani 1 1 d . . . H21 H 0.9527 -0.0446 0.2917 0.011 Uiso 1 1 calc R . . C22 C 0.9962(3) 0.1168(3) 0.23384(18) 0.0107(7) Uani 1 1 d . . . H22 H 1.0588 0.0869 0.2017 0.013 Uiso 1 1 calc R . . C23 C 0.9692(3) 0.2392(3) 0.22684(17) 0.0092(6) Uani 1 1 d . . . C24 C 1.0390(3) 0.3276(3) 0.17129(18) 0.0099(7) Uani 1 1 d . . . C25 C 0.8750(3) 0.2812(3) 0.27366(17) 0.0094(6) Uani 1 1 d . . . H25 H 0.8551 0.3644 0.2690 0.011 Uiso 1 1 calc R . . C26 C 0.8108(3) 0.2030(3) 0.32662(17) 0.0089(6) Uani 1 1 d . . . H26 H 0.7467 0.2327 0.3581 0.011 Uiso 1 1 calc R . . C27 C 0.1002(3) 0.2919(3) 0.83433(18) 0.0131(7) Uani 1 1 d . . . H27 H 0.0638 0.3632 0.8135 0.016 Uiso 1 1 calc R . . C28 C 0.0834(4) 0.1265(3) 0.9263(2) 0.0188(8) Uani 1 1 d . . . H28A H 0.1620 0.1020 0.9000 0.028 Uiso 1 1 calc R . . H28B H 0.0020 0.0554 0.9255 0.028 Uiso 1 1 calc R . . H28C H 0.1217 0.1510 0.9797 0.028 Uiso 1 1 calc R . . C29 C -0.0921(4) 0.2779(3) 0.9165(2) 0.0228(8) Uani 1 1 d . . . H29A H -0.0625 0.3088 0.9696 0.034 Uiso 1 1 calc R . . H29B H -0.1765 0.2095 0.9149 0.034 Uiso 1 1 calc R . . H29C H -0.1195 0.3463 0.8845 0.034 Uiso 1 1 calc R . . C30 C 0.3451(3) 0.0611(3) 0.0944(2) 0.0172(7) Uani 1 1 d . . . H30 H 0.2664 0.1056 0.0986 0.021 Uiso 1 1 calc R . . C31 C 0.4655(4) 0.1767(3) 0.2089(2) 0.0215(8) Uani 1 1 d . . . H31A H 0.3737 0.2109 0.2037 0.032 Uiso 1 1 calc R . . H31B H 0.5491 0.2452 0.2077 0.032 Uiso 1 1 calc R . . H31C H 0.4759 0.1335 0.2578 0.032 Uiso 1 1 calc R . . C32 C 0.5883(4) 0.0248(3) 0.1446(2) 0.0237(8) Uani 1 1 d . . . H32A H 0.5775 -0.0482 0.1777 0.036 Uiso 1 1 calc R . . H32B H 0.6791 0.0825 0.1630 0.036 Uiso 1 1 calc R . . H32C H 0.5929 -0.0031 0.0918 0.036 Uiso 1 1 calc R . . C33 C 0.3119(3) 0.5126(3) 0.04942(19) 0.0150(7) Uani 1 1 d . . . H33 H 0.3408 0.5187 0.1033 0.018 Uiso 1 1 calc R . . C34 C 0.3282(4) 0.6031(4) -0.0752(2) 0.0307(9) Uani 1 1 d . . . H34A H 0.2379 0.5419 -0.0885 0.046 Uiso 1 1 calc R . . H34B H 0.4070 0.5801 -0.1020 0.046 Uiso 1 1 calc R . . H34C H 0.3106 0.6868 -0.0907 0.046 Uiso 1 1 calc R . . C35 C 0.4809(4) 0.7084(3) 0.0408(2) 0.0233(8) Uani 1 1 d . . . H35A H 0.5015 0.6962 0.0961 0.035 Uiso 1 1 calc R . . H35B H 0.4430 0.7871 0.0321 0.035 Uiso 1 1 calc R . . H35C H 0.5717 0.7120 0.0169 0.035 Uiso 1 1 calc R . . N1 N 0.0305(3) 0.2318(2) 0.88757(15) 0.0115(6) Uani 1 1 d . . . N2 N 0.4623(3) 0.0888(2) 0.14620(16) 0.0153(6) Uani 1 1 d . . . N3 N 0.3712(3) 0.6038(2) 0.00678(16) 0.0145(6) Uani 1 1 d . . . O1 O 0.3017(2) -0.5763(2) 0.71155(13) 0.0154(5) Uani 1 1 d . . . H1 H 0.2777 -0.6254 0.7467 0.023 Uiso 1 1 calc R . . O2 O 0.5242(3) -0.5595(3) 0.77780(14) 0.0292(7) Uani 1 1 d . . . O3 O 0.7404(2) -0.01661(18) 0.59848(11) 0.0077(4) Uani 1 1 d . . . O4 O 0.8258(2) 0.21033(19) 0.69312(13) 0.0144(5) Uani 1 1 d . . . O5 O 0.8863(2) 0.39342(19) 0.56156(13) 0.0149(5) Uani 1 1 d . . . O6 O 0.8120(2) 0.15770(18) 0.48774(12) 0.0075(4) Uani 1 1 d . . . O7 O 1.0319(3) 0.4385(2) 0.17126(14) 0.0191(5) Uani 1 1 d . . . O8 O 1.1098(3) 0.2740(2) 0.12328(14) 0.0197(5) Uani 1 1 d . . . H8 H 1.1470 0.3280 0.0937 0.030 Uiso 1 1 calc R . . O9 O 0.2105(2) 0.2634(2) 0.80866(13) 0.0168(5) Uani 1 1 d . . . O10 O 0.3281(2) -0.0165(2) 0.04146(14) 0.0219(6) Uani 1 1 d . . . O11 O 0.2213(2) 0.4198(2) 0.02388(13) 0.0201(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(16) 0.0071(15) 0.0098(16) 0.0004(12) 0.0026(13) 0.0000(12) C2 0.0124(15) 0.0049(14) 0.0083(16) -0.0018(12) 0.0016(12) 0.0030(12) C3 0.0083(15) 0.0061(14) 0.0140(17) -0.0012(12) 0.0022(12) -0.0022(12) C4 0.0111(15) 0.0071(15) 0.0095(16) 0.0034(12) -0.0022(12) 0.0029(12) C5 0.0105(15) 0.0041(14) 0.0098(16) -0.0014(12) 0.0002(12) 0.0023(11) C6 0.0086(15) 0.0065(14) 0.0133(17) -0.0002(12) -0.0006(12) -0.0027(12) C7 0.0114(15) 0.0106(15) 0.0075(16) 0.0024(12) -0.0036(12) 0.0018(12) C8 0.0042(14) 0.0057(14) 0.0105(16) 0.0038(12) 0.0002(12) 0.0012(11) C9 0.0076(14) 0.0029(14) 0.0126(16) 0.0009(12) -0.0028(12) 0.0006(11) C10 0.0096(15) 0.0052(14) 0.0083(16) -0.0002(12) 0.0001(12) 0.0024(11) C11 0.0043(10) 0.0050(10) 0.0099(11) 0.0019(8) -0.0030(8) 0.0011(8) C12 0.0043(10) 0.0050(10) 0.0099(11) 0.0019(8) -0.0030(8) 0.0011(8) C13 0.0028(13) 0.0086(15) 0.0071(15) -0.0002(12) -0.0029(11) 0.0014(11) C14 0.0087(15) 0.0091(15) 0.0126(17) 0.0004(12) 0.0016(12) 0.0019(12) C15 0.0161(17) 0.0116(16) 0.0135(17) 0.0000(13) 0.0049(13) 0.0007(13) C16 0.0205(18) 0.0127(16) 0.0165(18) -0.0046(14) -0.0037(14) 0.0049(14) C17 0.0180(17) 0.0110(16) 0.0195(19) -0.0064(14) -0.0072(14) -0.0002(13) C18 0.0126(16) 0.0067(15) 0.027(2) -0.0019(14) 0.0044(14) -0.0038(13) C19 0.0065(15) 0.0074(15) 0.0187(18) -0.0007(13) 0.0001(13) 0.0002(12) C20 0.0071(14) 0.0079(15) 0.0073(16) 0.0014(12) -0.0034(12) -0.0014(12) C21 0.0114(15) 0.0048(14) 0.0095(16) 0.0006(12) -0.0045(12) -0.0006(12) C22 0.0080(15) 0.0101(15) 0.0130(17) 0.0002(13) -0.0006(12) 0.0000(12) C23 0.0072(14) 0.0103(15) 0.0074(16) 0.0018(12) -0.0044(12) -0.0024(12) C24 0.0066(15) 0.0109(16) 0.0104(16) 0.0023(12) -0.0059(12) 0.0012(12) C25 0.0131(16) 0.0056(14) 0.0081(16) 0.0022(12) -0.0041(12) 0.0009(12) C26 0.0089(15) 0.0090(15) 0.0084(16) -0.0001(12) -0.0012(12) 0.0018(12) C27 0.0148(16) 0.0083(15) 0.0142(17) 0.0027(13) 0.0015(13) -0.0034(13) C28 0.0226(18) 0.0181(18) 0.0160(19) 0.0079(14) 0.0034(15) 0.0035(14) C29 0.0191(18) 0.0231(19) 0.030(2) 0.0113(16) 0.0115(16) 0.0078(15) C30 0.0123(16) 0.0170(17) 0.022(2) 0.0042(15) 0.0024(14) 0.0023(13) C31 0.0221(18) 0.0249(19) 0.0167(19) -0.0031(15) 0.0030(15) 0.0015(15) C32 0.0163(18) 0.027(2) 0.026(2) -0.0047(16) -0.0058(15) 0.0071(15) C33 0.0184(17) 0.0173(17) 0.0114(17) 0.0044(14) 0.0050(14) 0.0071(14) C34 0.035(2) 0.033(2) 0.019(2) 0.0102(17) 0.0017(17) -0.0092(18) C35 0.0188(18) 0.0176(18) 0.031(2) -0.0007(16) 0.0000(16) -0.0019(14) N1 0.0127(13) 0.0112(13) 0.0111(14) 0.0050(11) 0.0031(11) 0.0023(11) N2 0.0137(14) 0.0169(14) 0.0147(15) -0.0010(12) -0.0011(12) 0.0028(11) N3 0.0173(14) 0.0118(14) 0.0142(15) 0.0045(11) 0.0025(11) 0.0012(11) O1 0.0122(11) 0.0156(12) 0.0161(13) 0.0063(10) 0.0037(9) -0.0054(9) O2 0.0195(13) 0.0451(17) 0.0176(14) 0.0199(12) -0.0028(11) -0.0067(12) O3 0.0110(10) 0.0076(10) 0.0044(11) -0.0002(8) -0.0016(8) 0.0030(8) O4 0.0125(11) 0.0088(11) 0.0198(13) -0.0019(9) -0.0042(9) -0.0001(9) O5 0.0178(12) 0.0083(11) 0.0180(13) -0.0016(9) -0.0051(10) 0.0055(9) O6 0.0067(10) 0.0030(10) 0.0107(11) 0.0000(8) -0.0030(8) -0.0025(8) O7 0.0279(13) 0.0085(12) 0.0224(14) 0.0068(10) 0.0094(11) 0.0033(10) O8 0.0288(13) 0.0127(12) 0.0210(14) 0.0092(10) 0.0156(11) 0.0046(10) O9 0.0195(12) 0.0161(12) 0.0166(13) 0.0043(10) 0.0096(10) 0.0031(10) O10 0.0207(13) 0.0217(13) 0.0206(14) -0.0041(11) -0.0043(10) 0.0009(10) O11 0.0245(13) 0.0161(12) 0.0174(13) 0.0033(10) 0.0065(10) -0.0059(10) _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 1.203(4) . ? C1 O1 1.317(4) . ? C1 C2 1.501(4) . ? C2 C3 1.388(4) . ? C2 C7 1.398(4) . ? C3 C4 1.387(4) . ? C3 H3 0.9500 . ? C4 C5 1.400(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 C8 1.492(4) . ? C6 C7 1.378(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.388(4) . ? C8 C13 1.399(4) . ? C9 C10 1.390(4) . ? C9 H9 0.9500 . ? C10 C11 1.401(4) . ? C10 H10 0.9500 . ? C11 C12 1.394(4) . ? C11 C20 1.490(4) . ? C12 O6 1.377(3) . ? C12 C13 1.398(4) . ? C13 O3 1.381(3) . ? C14 O3 1.446(3) . ? C14 C15 1.499(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O4 1.422(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O4 1.432(4) . ? C16 C17 1.499(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O5 1.422(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O5 1.423(4) . ? C18 C19 1.504(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O6 1.439(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.397(4) . ? C20 C26 1.399(4) . ? C21 C22 1.380(4) . ? C21 H21 0.9500 . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 C25 1.396(4) . ? C23 C24 1.492(4) . ? C24 O7 1.213(4) . ? C24 O8 1.317(4) . ? C25 C26 1.378(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O9 1.249(4) . ? C27 N1 1.310(4) . ? C27 H27 0.9500 . ? C28 N1 1.454(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 N1 1.459(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O10 1.228(4) . ? C30 N2 1.324(4) . ? C30 H30 0.9500 . ? C31 N2 1.446(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 N2 1.459(4) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 O11 1.240(4) . ? C33 N3 1.324(4) . ? C33 H33 0.9500 . ? C34 N3 1.445(4) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 N3 1.460(4) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? O1 H1 0.8400 . ? O8 H8 0.8400 . ? 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 O1 124.0(3) . . ? O2 C1 C2 122.4(3) . . ? O1 C1 C2 113.6(3) . . ? C3 C2 C7 119.3(3) . . ? C3 C2 C1 122.4(3) . . ? C7 C2 C1 118.3(3) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 C8 121.1(3) . . ? C4 C5 C8 119.7(3) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 120.2(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C9 C8 C13 118.2(3) . . ? C9 C8 C5 120.4(3) . . ? C13 C8 C5 121.5(3) . . ? C8 C9 C10 121.5(3) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 118.2(3) . . ? C12 C11 C20 121.7(3) . . ? C10 C11 C20 120.0(3) . . ? O6 C12 C11 119.7(3) . . ? O6 C12 C13 119.5(3) . . ? C11 C12 C13 120.8(3) . . ? O3 C13 C12 119.8(3) . . ? O3 C13 C8 119.6(3) . . ? C12 C13 C8 120.5(3) . . ? O3 C14 C15 106.8(2) . . ? O3 C14 H14A 110.4 . . ? C15 C14 H14A 110.4 . . ? O3 C14 H14B 110.4 . . ? C15 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? O4 C15 C14 111.8(3) . . ? O4 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? O4 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? O4 C16 C17 110.1(3) . . ? O4 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? O4 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.2 . . ? O5 C17 C16 112.4(3) . . ? O5 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? O5 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? O5 C18 C19 112.9(2) . . ? O5 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? O5 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? O6 C19 C18 106.7(2) . . ? O6 C19 H19A 110.4 . . ? C18 C19 H19A 110.4 . . ? O6 C19 H19B 110.4 . . ? C18 C19 H19B 110.4 . . ? H19A C19 H19B 108.6 . . ? C21 C20 C26 118.7(3) . . ? C21 C20 C11 119.3(3) . . ? C26 C20 C11 121.9(3) . . ? C22 C21 C20 120.6(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C25 119.1(3) . . ? C22 C23 C24 122.1(3) . . ? C25 C23 C24 118.8(3) . . ? O7 C24 O8 123.5(3) . . ? O7 C24 C23 122.8(3) . . ? O8 C24 C23 113.7(3) . . ? C26 C25 C23 120.5(3) . . ? C26 C25 H25 119.8 . . ? C23 C25 H25 119.8 . . ? C25 C26 C20 120.6(3) . . ? C25 C26 H26 119.7 . . ? C20 C26 H26 119.7 . . ? O9 C27 N1 125.5(3) . . ? O9 C27 H27 117.2 . . ? N1 C27 H27 117.2 . . ? N1 C28 H28A 109.5 . . ? N1 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N1 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N1 C29 H29A 109.5 . . ? N1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O10 C30 N2 126.4(3) . . ? O10 C30 H30 116.8 . . ? N2 C30 H30 116.8 . . ? N2 C31 H31A 109.5 . . ? N2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N2 C32 H32A 109.5 . . ? N2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O11 C33 N3 124.5(3) . . ? O11 C33 H33 117.8 . . ? N3 C33 H33 117.8 . . ? N3 C34 H34A 109.5 . . ? N3 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N3 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N3 C35 H35A 109.5 . . ? N3 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N3 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C27 N1 C28 121.3(3) . . ? C27 N1 C29 120.8(3) . . ? C28 N1 C29 117.5(3) . . ? C30 N2 C31 121.2(3) . . ? C30 N2 C32 120.7(3) . . ? C31 N2 C32 118.0(3) . . ? C33 N3 C34 120.7(3) . . ? C33 N3 C35 121.3(3) . . ? C34 N3 C35 117.9(3) . . ? C1 O1 H1 109.5 . . ? C13 O3 C14 115.7(2) . . ? C15 O4 C16 113.5(2) . . ? C17 O5 C18 116.2(2) . . ? C12 O6 C19 116.8(2) . . ? C24 O8 H8 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.342 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.101 data_BC-5.cif _database_code_depnum_ccdc_archive 'CCDC 883384' #Dr Lei Liu Nanyang Technological University, Singapore ##Prof.Qiaowei Li Fudan University, China #Wish to publish in Chem. Commun. _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 O9, 2(C2 H6 OS)' _chemical_formula_sum 'C32 H40 O11 S2' _chemical_formula_weight 664.76 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5432(16) _cell_length_b 10.5250(19) _cell_length_c 17.119(3) _cell_angle_alpha 105.358(8) _cell_angle_beta 93.281(9) _cell_angle_gamma 96.235(9) _cell_volume 1641.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 23.61 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9168 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 23865 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.1239 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5704 _reflns_number_gt 3305 _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^)+(0.0926P)^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 5704 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1250 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1827 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 C1 C -0.1230(5) -0.6336(4) 0.7443(2) 0.0226(10) Uani 1 1 d . . . C2 C -0.0436(4) -0.5143(4) 0.8057(2) 0.0191(10) Uani 1 1 d . . . C3 C 0.0855(4) -0.4528(4) 0.7926(2) 0.0209(10) Uani 1 1 d . . . H3 H 0.1252 -0.4848 0.7426 0.025 Uiso 1 1 calc R . . C4 C 0.1578(4) -0.3447(4) 0.8520(2) 0.0216(10) Uani 1 1 d . . . H4 H 0.2463 -0.3036 0.8424 0.026 Uiso 1 1 calc R . . C5 C 0.0999(4) -0.2965(4) 0.9257(2) 0.0199(10) Uani 1 1 d . . . C6 C -0.0315(4) -0.3576(4) 0.9387(2) 0.0235(10) Uani 1 1 d . . . H6 H -0.0718 -0.3254 0.9885 0.028 Uiso 1 1 calc R . . C7 C -0.1031(4) -0.4652(4) 0.8787(2) 0.0207(10) Uani 1 1 d . . . H7 H -0.1927 -0.5055 0.8874 0.025 Uiso 1 1 calc R . . C8 C 0.1748(4) -0.1816(4) 0.9904(2) 0.0183(10) Uani 1 1 d . . . C9 C 0.2037(4) -0.1927(4) 1.0697(2) 0.0213(10) Uani 1 1 d . . . H9 H 0.1726 -0.2733 1.0821 0.026 Uiso 1 1 calc R . . C10 C 0.2771(4) -0.0870(4) 1.1300(2) 0.0216(10) Uani 1 1 d . . . H10 H 0.2995 -0.0985 1.1823 0.026 Uiso 1 1 calc R . . C11 C 0.3185(4) 0.0347(4) 1.1158(2) 0.0187(10) Uani 1 1 d . . . C12 C 0.2836(4) 0.0494(4) 1.0380(2) 0.0169(9) Uani 1 1 d . . . C13 C 0.2193(4) -0.0599(4) 0.9752(2) 0.0189(10) Uani 1 1 d . . . C14 C 0.0800(4) 0.0040(4) 0.8738(2) 0.0249(10) Uani 1 1 d . . . H14A H 0.1046 0.0990 0.8764 0.030 Uiso 1 1 calc R . . H14B H 0.0075 -0.0028 0.9121 0.030 Uiso 1 1 calc R . . C15 C 0.0222(5) -0.0736(4) 0.7880(2) 0.0277(11) Uani 1 1 d . . . H15A H 0.0099 -0.1696 0.7845 0.033 Uiso 1 1 calc R . . H15B H -0.0722 -0.0485 0.7763 0.033 Uiso 1 1 calc R . . C16 C 0.0813(5) 0.0614(4) 0.7023(3) 0.0299(11) Uani 1 1 d . . . H16A H 0.0686 0.1354 0.7499 0.036 Uiso 1 1 calc R . . H16B H -0.0072 0.0392 0.6656 0.036 Uiso 1 1 calc R . . C17 C 0.2014(5) 0.1023(5) 0.6588(3) 0.0370(12) Uani 1 1 d . . . H17A H 0.2243 0.0232 0.6178 0.044 Uiso 1 1 calc R . . H17B H 0.1720 0.1659 0.6296 0.044 Uiso 1 1 calc R . . C18 C 0.3195(5) 0.2989(5) 0.7541(3) 0.0388(13) Uani 1 1 d . . . H18A H 0.2223 0.3102 0.7695 0.047 Uiso 1 1 calc R . . H18B H 0.3435 0.3556 0.7178 0.047 Uiso 1 1 calc R . . C19 C 0.4216(5) 0.3405(5) 0.8291(3) 0.0340(12) Uani 1 1 d . . . H19A H 0.5177 0.3221 0.8146 0.041 Uiso 1 1 calc R . . H19B H 0.4250 0.4370 0.8547 0.041 Uiso 1 1 calc R . . C20 C 0.4559(5) 0.3116(4) 0.9609(3) 0.0285(11) Uani 1 1 d . . . H20A H 0.4160 0.3864 0.9968 0.034 Uiso 1 1 calc R . . H20B H 0.5552 0.3422 0.9543 0.034 Uiso 1 1 calc R . . C21 C 0.4502(4) 0.1973(4) 0.9973(3) 0.0268(11) Uani 1 1 d . . . H21A H 0.4740 0.1178 0.9571 0.032 Uiso 1 1 calc R . . H21B H 0.5203 0.2186 1.0453 0.032 Uiso 1 1 calc R . . C22 C 0.4057(4) 0.1421(4) 1.1808(2) 0.0192(10) Uani 1 1 d . . . C23 C 0.3682(4) 0.2705(4) 1.2057(2) 0.0227(10) Uani 1 1 d . . . H23 H 0.2882 0.2924 1.1788 0.027 Uiso 1 1 calc R . . C24 C 0.4469(4) 0.3666(4) 1.2695(2) 0.0223(10) Uani 1 1 d . . . H24 H 0.4207 0.4537 1.2860 0.027 Uiso 1 1 calc R . . C25 C 0.5648(4) 0.3345(4) 1.3090(2) 0.0177(9) Uani 1 1 d . . . C26 C 0.6502(5) 0.4320(4) 1.3806(2) 0.0236(10) Uani 1 1 d . . . C27 C 0.6053(4) 0.2082(4) 1.2828(2) 0.0207(10) Uani 1 1 d . . . H27 H 0.6875 0.1872 1.3082 0.025 Uiso 1 1 calc R . . C28 C 0.5251(4) 0.1127(4) 1.2193(2) 0.0183(9) Uani 1 1 d . . . H28 H 0.5524 0.0262 1.2021 0.022 Uiso 1 1 calc R . . C29 C 0.8680(5) 0.5867(4) 0.6053(3) 0.0339(12) Uani 1 1 d . . . H29A H 0.7964 0.5572 0.6378 0.051 Uiso 1 1 calc R . . H29B H 0.9623 0.5945 0.6333 0.051 Uiso 1 1 calc R . . H29C H 0.8623 0.5219 0.5519 0.051 Uiso 1 1 calc R . . C30 C 0.9758(5) 0.7623(5) 0.5301(3) 0.0407(13) Uani 1 1 d . . . H30A H 0.9646 0.6864 0.4815 0.061 Uiso 1 1 calc R . . H30B H 1.0672 0.7664 0.5605 0.061 Uiso 1 1 calc R . . H30C H 0.9722 0.8445 0.5139 0.061 Uiso 1 1 calc R . . C31 C 0.5914(5) 0.2263(4) 0.5635(3) 0.0340(12) Uani 1 1 d . . . H31A H 0.6143 0.2804 0.6198 0.051 Uiso 1 1 calc R . . H31B H 0.4884 0.2075 0.5517 0.051 Uiso 1 1 calc R . . H31C H 0.6312 0.2747 0.5265 0.051 Uiso 1 1 calc R . . C32 C 0.5980(4) 0.0231(4) 0.6331(2) 0.0259(11) Uani 1 1 d . . . H32A H 0.6313 -0.0612 0.6346 0.039 Uiso 1 1 calc R . . H32B H 0.4944 0.0114 0.6267 0.039 Uiso 1 1 calc R . . H32C H 0.6318 0.0910 0.6839 0.039 Uiso 1 1 calc R . . O1 O -0.0564(3) -0.6731(3) 0.67743(16) 0.0248(7) Uani 1 1 d . . . H1 H -0.0935 -0.7494 0.6506 0.037 Uiso 1 1 calc R . . O2 O -0.2363(3) -0.6865(3) 0.75565(17) 0.0346(8) Uani 1 1 d . . . O3 O 0.7611(3) 0.4120(3) 1.41092(18) 0.0392(9) Uani 1 1 d . . . O4 O 0.5898(3) 0.5415(3) 1.40804(17) 0.0300(8) Uani 1 1 d . . . H4A H 0.6417 0.5938 1.4472 0.045 Uiso 1 1 calc R . . O5 O 0.2042(3) -0.0494(3) 0.89626(14) 0.0191(7) Uani 1 1 d . . . O6 O 0.1105(3) -0.0514(3) 0.72843(15) 0.0261(7) Uani 1 1 d . . . O7 O 0.3260(3) 0.1626(3) 0.71236(18) 0.0361(8) Uani 1 1 d . . . O8 O 0.3755(3) 0.2684(3) 0.88352(18) 0.0405(9) Uani 1 1 d . . . O9 O 0.3105(3) 0.1707(3) 1.02109(15) 0.0188(7) Uani 1 1 d . . . O10 O 0.7007(3) 0.7220(3) 0.53831(16) 0.0307(8) Uani 1 1 d . . . O11 O 0.8243(3) 0.1111(3) 0.57158(15) 0.0255(7) Uani 1 1 d . . . S1 S 0.83712(11) 0.74318(11) 0.59268(6) 0.0250(3) Uani 1 1 d . . . S2 S 0.66464(11) 0.07379(11) 0.54984(6) 0.0228(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(3) 0.020(3) 0.020(2) -0.001(2) -0.0085(19) 0.002(2) C2 0.020(3) 0.017(2) 0.015(2) -0.0015(18) -0.0058(17) -0.0007(18) C3 0.024(3) 0.023(2) 0.012(2) -0.0009(19) -0.0011(17) 0.0021(19) C4 0.018(2) 0.022(2) 0.018(2) -0.0005(19) -0.0019(18) -0.0064(19) C5 0.022(3) 0.018(2) 0.017(2) 0.0014(19) -0.0026(18) -0.0007(19) C6 0.028(3) 0.021(2) 0.017(2) -0.0028(19) -0.0009(18) 0.001(2) C7 0.014(2) 0.022(2) 0.020(2) 0.0007(19) -0.0041(18) -0.0061(18) C8 0.012(2) 0.024(3) 0.013(2) -0.0032(19) -0.0020(16) -0.0018(18) C9 0.019(2) 0.023(2) 0.018(2) 0.0007(19) -0.0027(18) -0.0026(19) C10 0.019(3) 0.028(3) 0.013(2) 0.001(2) -0.0075(17) 0.0018(19) C11 0.019(2) 0.021(2) 0.013(2) -0.0002(19) -0.0030(17) 0.0018(18) C12 0.012(2) 0.017(2) 0.017(2) -0.0013(19) -0.0042(17) 0.0000(18) C13 0.015(2) 0.026(3) 0.012(2) 0.0004(19) -0.0002(17) 0.0005(19) C14 0.024(3) 0.032(3) 0.016(2) 0.003(2) -0.0059(18) 0.007(2) C15 0.029(3) 0.031(3) 0.015(2) -0.004(2) -0.0087(19) 0.002(2) C16 0.033(3) 0.034(3) 0.024(2) 0.009(2) 0.000(2) 0.009(2) C17 0.038(3) 0.054(3) 0.021(2) 0.010(2) 0.002(2) 0.016(3) C18 0.051(4) 0.038(3) 0.033(3) 0.015(3) 0.008(2) 0.010(3) C19 0.033(3) 0.033(3) 0.038(3) 0.017(2) 0.001(2) -0.004(2) C20 0.022(3) 0.029(3) 0.031(3) 0.006(2) -0.001(2) -0.002(2) C21 0.018(3) 0.031(3) 0.029(3) 0.006(2) 0.0003(19) -0.001(2) C22 0.019(3) 0.021(2) 0.012(2) -0.0009(18) -0.0004(17) -0.0034(19) C23 0.021(3) 0.028(3) 0.013(2) -0.0018(19) -0.0085(17) 0.001(2) C24 0.020(3) 0.025(3) 0.016(2) -0.0027(19) -0.0050(18) 0.0013(19) C25 0.014(2) 0.023(2) 0.010(2) -0.0043(18) -0.0041(16) -0.0038(18) C26 0.027(3) 0.024(3) 0.015(2) 0.000(2) 0.0024(19) -0.002(2) C27 0.018(2) 0.026(3) 0.014(2) 0.0006(19) -0.0033(17) -0.0001(19) C28 0.019(2) 0.018(2) 0.013(2) -0.0034(18) -0.0042(17) 0.0025(18) C29 0.034(3) 0.039(3) 0.028(3) 0.008(2) 0.001(2) 0.010(2) C30 0.035(3) 0.057(4) 0.027(3) 0.010(3) -0.004(2) -0.001(3) C31 0.033(3) 0.026(3) 0.036(3) 0.003(2) -0.017(2) 0.000(2) C32 0.028(3) 0.029(3) 0.015(2) 0.000(2) -0.0065(18) 0.002(2) O1 0.0256(18) 0.0197(17) 0.0184(16) -0.0087(13) -0.0021(13) -0.0064(13) O2 0.028(2) 0.038(2) 0.0242(17) -0.0080(15) -0.0016(14) -0.0132(15) O3 0.028(2) 0.040(2) 0.0331(19) -0.0152(16) -0.0219(15) 0.0095(16) O4 0.034(2) 0.0215(18) 0.0230(17) -0.0103(14) -0.0157(13) 0.0021(15) O5 0.0172(17) 0.0242(17) 0.0115(14) -0.0012(12) -0.0049(11) 0.0022(12) O6 0.0298(19) 0.0336(19) 0.0148(15) 0.0032(14) 0.0011(13) 0.0120(14) O7 0.034(2) 0.040(2) 0.0334(18) 0.0066(16) 0.0056(15) 0.0091(15) O8 0.036(2) 0.051(2) 0.0332(19) 0.0203(17) -0.0107(15) -0.0167(16) O9 0.0188(17) 0.0196(16) 0.0154(15) 0.0025(12) -0.0025(11) -0.0009(12) O10 0.0235(18) 0.0308(18) 0.0279(17) -0.0062(14) -0.0146(13) 0.0053(14) O11 0.0186(18) 0.0273(18) 0.0203(15) -0.0087(13) -0.0046(12) -0.0003(13) S1 0.0232(7) 0.0289(7) 0.0153(6) -0.0036(5) -0.0077(4) -0.0006(5) S2 0.0223(7) 0.0249(7) 0.0144(5) -0.0026(5) -0.0072(4) -0.0019(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.211(5) . ? C1 O1 1.333(5) . ? C1 C2 1.503(6) . ? C2 C3 1.387(6) . ? C2 C7 1.398(5) . ? C3 C4 1.393(5) . ? C3 H3 0.9500 . ? C4 C5 1.399(5) . ? C4 H4 0.9500 . ? C5 C6 1.402(6) . ? C5 C8 1.488(5) . ? C6 C7 1.393(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.399(6) . ? C8 C9 1.407(5) . ? C9 C10 1.391(6) . ? C9 H9 0.9500 . ? C10 C11 1.386(6) . ? C10 H10 0.9500 . ? C11 C12 1.405(5) . ? C11 C22 1.494(5) . ? C12 O9 1.384(5) . ? C12 C13 1.405(5) . ? C13 O5 1.385(4) . ? C14 O5 1.441(5) . ? C14 C15 1.518(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O6 1.409(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O6 1.423(5) . ? C16 C17 1.488(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O7 1.436(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O7 1.433(5) . ? C18 C19 1.501(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O8 1.410(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O8 1.428(5) . ? C20 C21 1.491(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O9 1.437(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C28 1.389(5) . ? C22 C23 1.397(6) . ? C23 C24 1.391(5) . ? C23 H23 0.9500 . ? C24 C25 1.398(5) . ? C24 H24 0.9500 . ? C25 C27 1.391(5) . ? C25 C26 1.503(6) . ? C26 O3 1.215(5) . ? C26 O4 1.330(5) . ? C27 C28 1.392(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 S1 1.770(5) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 S1 1.777(5) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 S2 1.784(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 S2 1.776(4) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? O1 H1 0.8400 . ? O4 H4A 0.8400 . ? O10 S1 1.516(3) . ? O11 S2 1.530(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 124.5(4) . . ? O2 C1 C2 122.3(4) . . ? O1 C1 C2 113.2(4) . . ? C3 C2 C7 119.4(4) . . ? C3 C2 C1 122.5(4) . . ? C7 C2 C1 118.0(4) . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 C8 121.3(4) . . ? C6 C5 C8 119.5(3) . . ? C7 C6 C5 120.2(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 120.2(4) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C13 C8 C9 117.8(4) . . ? C13 C8 C5 121.9(3) . . ? C9 C8 C5 120.4(4) . . ? C10 C9 C8 120.8(4) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 121.6(4) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 118.1(4) . . ? C10 C11 C22 119.6(3) . . ? C12 C11 C22 122.2(4) . . ? O9 C12 C13 118.1(3) . . ? O9 C12 C11 121.5(3) . . ? C13 C12 C11 120.4(4) . . ? O5 C13 C8 119.2(3) . . ? O5 C13 C12 119.8(4) . . ? C8 C13 C12 120.9(4) . . ? O5 C14 C15 109.0(3) . . ? O5 C14 H14A 109.9 . . ? C15 C14 H14A 109.9 . . ? O5 C14 H14B 109.9 . . ? C15 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O6 C15 C14 113.1(4) . . ? O6 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? O6 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? O6 C16 C17 109.1(4) . . ? O6 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O6 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? O7 C17 C16 112.8(4) . . ? O7 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? O7 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? O7 C18 C19 109.9(4) . . ? O7 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? O7 C18 H18B 109.7 . . ? C19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? O8 C19 C18 108.3(4) . . ? O8 C19 H19A 110.0 . . ? C18 C19 H19A 110.0 . . ? O8 C19 H19B 110.0 . . ? C18 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? O8 C20 C21 108.2(3) . . ? O8 C20 H20A 110.1 . . ? C21 C20 H20A 110.1 . . ? O8 C20 H20B 110.1 . . ? C21 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? O9 C21 C20 109.4(3) . . ? O9 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? O9 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? C28 C22 C23 118.9(4) . . ? C28 C22 C11 119.1(4) . . ? C23 C22 C11 121.9(4) . . ? C24 C23 C22 120.7(4) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.6(4) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C27 C25 C24 120.0(4) . . ? C27 C25 C26 117.8(4) . . ? C24 C25 C26 122.2(4) . . ? O3 C26 O4 123.7(4) . . ? O3 C26 C25 123.7(4) . . ? O4 C26 C25 112.6(4) . . ? C25 C27 C28 119.8(4) . . ? C25 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C22 C28 C27 120.9(4) . . ? C22 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? S1 C29 H29A 109.5 . . ? S1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? S1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? S1 C30 H30A 109.5 . . ? S1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? S1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? S2 C31 H31A 109.5 . . ? S2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? S2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? S2 C32 H32A 109.5 . . ? S2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? S2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C1 O1 H1 109.5 . . ? C26 O4 H4A 109.5 . . ? C13 O5 C14 116.6(3) . . ? C15 O6 C16 112.0(3) . . ? C18 O7 C17 112.8(3) . . ? C19 O8 C20 112.9(3) . . ? C12 O9 C21 114.1(3) . . ? O10 S1 C29 107.5(2) . . ? O10 S1 C30 105.81(19) . . ? C29 S1 C30 97.7(2) . . ? O11 S2 C32 105.78(18) . . ? O11 S2 C31 106.40(19) . . ? C32 S2 C31 99.4(2) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.378 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.102 data_mof-bc4 _database_code_depnum_ccdc_archive 'CCDC 883385' #TrackingRef 'web_deposit_cif_file_0_YanliZhao_1352155281.883385.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 12C4 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C70 H48 O21 Zn4' _chemical_formula_weight 1486.64 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P42/ncm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z+1/2' 'y, -x+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' 'y+1/2, x+1/2, -z' '-y, -x, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z-1/2' '-y, x-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' '-y-1/2, -x-1/2, z' 'y, x, z' _cell_length_a 21.4901(11) _cell_length_b 21.4901(11) _cell_length_c 42.883(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 19805(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 1526 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 21.23 _exptl_crystal_description cube _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 0.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7525 _exptl_absorpt_correction_T_max 0.7525 _exptl_absorpt_process_details sadabs _exptl_special_details ; The crystal was weakly diffracting and the structure is extensively disordered. The data collection has relatively low theta(max). ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.022 0.008 -0.001 13197 2485 ' ' _platon_squeeze_details ; Very little remaining electron density was left, because of the highly disordered nature of the crown ethers and solvent molecules. The highly diffused electron density makes impossible to locate these atoms. SQUEEZE shows about 2485 electron counts in voids in each unit cell, 328 electrons are from 4 unresolved crown ethers, and 2157 electrons from estimated solvents (about 34 DMF in one unit cell, 8.5 DMF per [Zn4O(C26H22O8)3]). ; _diffrn_ambient_temperature 143(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_reflns_number 77217 _diffrn_reflns_av_R_equivalents 0.1495 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 22.60 _reflns_number_total 6856 _reflns_number_gt 3309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In the structure, 17 DFIX, 5 ISOR, and 1 delu instructions were used to refine disordered ligand so that there were 42 restraints. The modeled structure formula is C70 H24 O19 Zn4. Including the unresolved crown ethers, and the solvents, the full formula of the structure is [Zn4O(C26H22O8)3].8.5(C7H7NO). ; _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^)+(0.1327P)^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 6856 _refine_ls_number_parameters 255 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2301 _refine_ls_wR_factor_gt 0.2138 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.005 _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 Zn1 Zn 0.301188(8) 0.198812(8) 0.523071(6) 0.04762(7) Uani 1 2 d S . . Zn2 Zn 0.302504(9) 0.302504(9) 0.575712(6) 0.05704(9) Uani 1 2 d S . . O1 O 0.2500 0.2500 0.54904(4) 0.0310(5) Uani 1 4 d S . . O2 O 0.28641(5) 0.21359(5) 0.47915(3) 0.0792(6) Uani 1 2 d S . . O3 O 0.21181(6) 0.39016(5) 0.52795(3) 0.0945(5) Uani 1 1 d . . . O4 O 0.28942(6) 0.38757(5) 0.56306(4) 0.1062(6) Uani 1 1 d . . . O5 O 0.21134(9) 0.28866(9) 0.11895(5) 0.2020(14) Uani 1 2 d S . . C1 C 0.2500 0.2500 0.46464(7) 0.0613(11) Uani 1 4 d S . . C2 C 0.2500 0.2500 0.43067(7) 0.0849(13) Uani 1 4 d S . . C3 C 0.28743(11) 0.21257(11) 0.41416(7) 0.1476(15) Uani 1 2 d SU . . H3 H 0.3150 0.1850 0.4246 0.177 Uiso 1 2 calc SR . . C4 C 0.28569(12) 0.21431(12) 0.38168(7) 0.2031(18) Uani 1 2 d S . . H4 H 0.3134 0.1866 0.3714 0.244 Uiso 1 2 calc SR . . C5 C 0.2500 0.2500 0.36254(10) 0.178(2) Uani 1 4 d SDU . . C6 C 0.2500 0.2500 0.32732(9) 0.197(3) Uani 1 4 d SD . . C7 C 0.2407(6) 0.1920(2) 0.31129(11) 0.459(8) Uani 0.50 1 d PD . . C8 C 0.2331(4) 0.1889(2) 0.27727(13) 0.295(5) Uiso 0.50 1 d PD . . C9 C 0.2500 0.2500 0.26571(12) 0.207(3) Uiso 1 4 d SD . . C10 C 0.2500 0.2500 0.23003(16) 0.209(3) Uiso 1 4 d S . . C11 C 0.21059(18) 0.28941(18) 0.21489(15) 0.252(3) Uiso 1 2 d S . . H11 H 0.1835 0.3165 0.2260 0.302 Uiso 1 2 calc SR . . C12 C 0.21187(19) 0.28813(19) 0.18244(16) 0.278(3) Uiso 1 2 d S . . H12 H 0.1845 0.3155 0.1717 0.333 Uiso 1 2 calc SR . . C13 C 0.2500 0.2500 0.16456(13) 0.314(5) Uiso 1 4 d SD . . C14 C 0.2500 0.2500 0.13013(15) 0.488(8) Uiso 1 4 d SD . . C15 C 0.25106(10) 0.41558(8) 0.54558(4) 0.0941(8) Uani 1 1 d . . . C16 C 0.25497(12) 0.48527(8) 0.54628(5) 0.1173(10) Uani 1 1 d . . . C17 C 0.28994(12) 0.51926(8) 0.56364(7) 0.1429(12) Uani 1 1 d . . . H13 H 0.3176 0.4978 0.5771 0.171 Uiso 1 1 calc R . . C18 C 0.29172(12) 0.58077(9) 0.56484(6) 0.1505(12) Uani 1 1 d D . . H14 H 0.3186 0.6005 0.5794 0.181 Uiso 1 1 calc R . . C19 C 0.25645(17) 0.61590(9) 0.54592(6) 0.1822(15) Uani 1 1 d D . . C20 C 0.21384(18) 0.58407(11) 0.52857(7) 0.2212(18) Uani 1 1 d U . . H16 H 0.1841 0.6069 0.5168 0.265 Uiso 1 1 calc R . . C21 C 0.21225(15) 0.51651(15) 0.52743(8) 0.1903(14) Uiso 1 1 d U . . H17 H 0.1836 0.4948 0.5145 0.228 Uiso 1 1 calc R . . C22 C 0.2562(2) 0.68580(19) 0.54622(9) 0.1064(17) Uani 0.50 1 d PU . . C23 C 0.3247(2) 0.71714(16) 0.55178(10) 0.0913(16) Uani 0.50 1 d PU . . C24 C 0.32685(16) 0.78305(18) 0.54913(9) 0.0862(13) Uiso 0.50 1 d PD . . C25 C 0.28078(15) 0.7945(2) 0.54367(10) 0.0960(17) Uani 0.50 1 d P . . C26 C 0.2172(2) 0.7911(2) 0.54188(12) 0.1209(17) Uiso 0.50 1 d PD . . C27 C 0.4227(2) 0.6717(3) 0.52778(12) 0.154(2) Uiso 0.50 1 d PD . . H27A H 0.3958 0.6453 0.5145 0.185 Uiso 0.50 1 calc PR . . H27B H 0.4288 0.7114 0.5165 0.185 Uiso 0.50 1 calc PR . . C28 C 0.4793(2) 0.6432(3) 0.52971(15) 0.260(4) Uiso 0.50 1 d PD . . H28A H 0.5021 0.6462 0.5097 0.312 Uiso 0.50 1 calc PR . . H28B H 0.4748 0.5988 0.5354 0.312 Uiso 0.50 1 calc PR . . C29 C 0.5633(3) 0.7047(3) 0.5474(2) 0.347(6) Uiso 0.50 1 d PD . . H29A H 0.5602 0.7256 0.5268 0.416 Uiso 0.50 1 calc PR . . H29B H 0.5985 0.6750 0.5473 0.416 Uiso 0.50 1 calc PR . . C30 C 0.56754(19) 0.7624(2) 0.58107(16) 0.537(10) Uiso 0.50 1 d PD . . H30A H 0.5546 0.7442 0.6013 0.645 Uiso 0.50 1 calc PR . . H30B H 0.6087 0.7827 0.5830 0.645 Uiso 0.50 1 calc PR . . C31 C 0.48283(18) 0.8402(2) 0.58441(13) 0.352(6) Uiso 0.50 1 d PD . . H31A H 0.4908 0.8825 0.5762 0.422 Uiso 0.50 1 calc PR . . H31B H 0.4982 0.8402 0.6062 0.422 Uiso 0.50 1 calc PR . . C32 C 0.4090(3) 0.8339(3) 0.58680(16) 0.213(3) Uiso 0.50 1 d P . . H32A H 0.3976 0.8019 0.6024 0.256 Uiso 0.50 1 calc PR . . H32B H 0.3902 0.8740 0.5931 0.256 Uiso 0.50 1 calc PR . . O6 O 0.38721(14) 0.68600(10) 0.55691(8) 0.1206(13) Uani 0.50 1 d PD . . O7 O 0.51292(15) 0.67974(19) 0.55551(11) 0.224(2) Uani 0.50 1 d PD . . O8 O 0.52263(14) 0.80067(15) 0.56791(10) 0.314(3) Uani 0.50 1 d PD . . O9 O 0.38773(14) 0.81622(12) 0.55668(9) 0.1462(16) Uani 0.50 1 d PD . . 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 Zn1 0.04878(9) 0.04878(9) 0.04530(14) -0.00125(9) 0.00125(9) 0.01593(13) Zn2 0.05685(10) 0.05685(10) 0.05743(17) -0.00222(10) -0.00222(10) -0.00632(15) O1 0.0269(5) 0.0269(5) 0.0392(10) 0.000 0.000 0.0006(9) O2 0.0937(7) 0.0937(7) 0.0500(9) 0.0082(6) -0.0082(6) 0.0403(9) O3 0.1503(11) 0.0416(7) 0.0918(9) -0.0028(7) -0.0135(9) 0.0429(7) O4 0.0897(9) 0.0464(7) 0.1826(13) 0.0038(9) -0.0163(10) 0.0101(7) O5 0.276(2) 0.276(2) 0.0532(12) -0.0350(11) 0.0350(11) -0.008(2) C1 0.0799(14) 0.0799(14) 0.0241(15) 0.000 0.000 -0.003(2) C2 0.1164(18) 0.1164(18) 0.0220(17) 0.000 0.000 0.034(3) C3 0.191(2) 0.191(2) 0.0614(18) 0.0088(13) -0.0088(13) 0.073(2) C4 0.275(3) 0.275(3) 0.059(2) -0.0252(15) 0.0252(15) 0.135(3) C5 0.208(3) 0.208(3) 0.118(4) 0.000 0.000 0.025(4) C6 0.250(4) 0.250(4) 0.092(4) 0.000 0.000 0.012(7) C7 0.622(18) 0.202(9) 0.553(13) -0.109(7) -0.248(12) 0.008(11) C15 0.1434(18) 0.0420(10) 0.0968(15) 0.0110(11) 0.0167(15) -0.0015(13) C16 0.198(2) 0.0359(10) 0.1184(16) 0.0150(12) 0.0140(18) 0.0346(13) C17 0.163(2) 0.0290(11) 0.236(3) -0.0095(15) -0.021(2) -0.0133(14) C18 0.214(3) 0.0391(12) 0.199(2) -0.0013(15) 0.057(2) -0.0242(15) C19 0.371(4) 0.0341(11) 0.141(2) 0.0010(14) 0.006(3) -0.031(2) C20 0.409(4) 0.0683(16) 0.186(3) 0.0194(18) -0.072(3) 0.039(2) C22 0.139(3) 0.082(3) 0.098(3) -0.014(2) 0.039(3) -0.005(3) C23 0.116(3) 0.0333(19) 0.124(3) 0.010(2) -0.003(3) -0.002(2) C25 0.0178(16) 0.159(4) 0.112(3) 0.004(3) 0.004(2) 0.022(2) O6 0.131(2) 0.0339(14) 0.196(3) 0.0013(17) -0.002(2) -0.0071(16) O7 0.103(2) 0.241(4) 0.329(5) 0.083(4) 0.056(3) 0.064(3) O8 0.140(3) 0.250(5) 0.553(9) 0.055(5) -0.135(4) -0.095(3) O9 0.107(2) 0.0518(16) 0.280(4) 0.028(2) 0.007(3) 0.0109(16) _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 Zn1 O1 1.9132(10) . ? Zn1 O2 1.9363(15) . ? Zn1 O3 1.9436(11) 16 ? Zn1 O3 1.9436(11) 2 ? Zn1 Zn1 3.1113(5) 2 ? Zn2 O5 1.901(2) 4 ? Zn2 O4 1.9274(12) 16 ? Zn2 O4 1.9275(12) . ? Zn2 O1 1.9632(10) . ? O1 Zn1 1.9131(10) 2 ? O1 Zn2 1.9633(10) 2 ? O2 C1 1.270(2) . ? O3 C15 1.258(2) . ? O3 Zn1 1.9436(11) 2 ? O4 C15 1.266(2) . ? O5 C14 1.269(4) . ? O5 Zn2 1.901(2) 3_554 ? C1 O2 1.270(2) 2 ? C1 C2 1.457(4) . ? C2 C3 1.340(4) 2 ? C2 C3 1.340(4) . ? C3 C4 1.394(4) . ? C3 H3 0.9500 . ? C4 C5 1.360(4) . ? C4 H4 0.9500 . ? C5 C4 1.360(4) 2 ? C5 C6 1.510(6) . ? C6 C7 1.437(6) . ? C6 C7 1.437(6) 16 ? C6 C7 1.437(6) 15_665 ? C6 C7 1.437(6) 2 ? C7 C8 1.470(7) . ? C7 C7 1.48(2) 16 ? C7 C8 2.037(11) 16 ? C7 C7 2.04(2) 15_665 ? C8 C8 1.342(15) 16 ? C8 C9 1.449(6) . ? C8 C7 2.037(11) 16 ? C9 C8 1.449(6) 15_665 ? C9 C8 1.449(6) 2 ? C9 C8 1.449(6) 16 ? C9 C10 1.530(8) . ? C10 C11 1.362(6) 2 ? C10 C11 1.362(6) . ? C11 C12 1.392(9) . ? C11 H11 0.9500 . ? C12 C13 1.389(7) . ? C12 H12 0.9500 . ? C13 C12 1.389(7) 2 ? C13 C14 1.477(8) . ? C14 O5 1.269(4) 2 ? C15 C16 1.500(2) . ? C16 C17 1.286(3) . ? C16 C21 1.395(4) . ? C17 C18 1.323(3) . ? C17 H13 0.9500 . ? C18 C19 1.343(4) . ? C18 H14 0.9500 . ? C19 C20 1.364(4) . ? C19 C22 1.502(5) . ? C20 C21 1.453(4) . ? C20 H16 0.9500 . ? C21 H17 0.9500 . ? C22 C26 0.779(6) 2_565 ? C22 C25 0.907(6) 2_565 ? C22 C23 1.635(6) . ? C22 C24 1.910(6) 2_565 ? C23 C26 1.011(6) 2_565 ? C23 C24 1.422(5) . ? C23 O6 1.518(5) . ? C24 C25 1.047(5) . ? C24 O9 1.525(5) . ? C24 C26 1.880(6) 2_565 ? C24 C22 1.910(6) 2_565 ? C25 C22 0.907(6) 2_565 ? C25 C26 1.370(5) . ? C25 C26 1.842(7) 2_565 ? C26 C22 0.779(6) 2_565 ? C26 C23 1.011(6) 2_565 ? C26 C25 1.842(7) 2_565 ? C26 C24 1.880(6) 2_565 ? C27 C28 1.364(7) . ? C27 O6 1.496(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 O7 1.537(7) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O7 1.258(7) . ? C29 C30 1.906(10) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O8 1.389(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O8 1.398(5) . ? C31 C32 1.596(8) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O9 1.422(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? 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 O1 Zn1 O2 112.19(6) . . ? O1 Zn1 O3 114.86(4) . 16 ? O2 Zn1 O3 104.04(5) . 16 ? O1 Zn1 O3 114.86(4) . 2 ? O2 Zn1 O3 104.04(5) . 2 ? O3 Zn1 O3 105.73(8) 16 2 ? O1 Zn1 Zn1 35.60(4) . 2 ? O2 Zn1 Zn1 76.59(5) . 2 ? O3 Zn1 Zn1 126.44(4) 16 2 ? O3 Zn1 Zn1 126.44(4) 2 2 ? O5 Zn2 O4 113.58(7) 4 16 ? O5 Zn2 O4 113.59(7) 4 . ? O4 Zn2 O4 101.39(8) 16 . ? O5 Zn2 O1 112.85(10) 4 . ? O4 Zn2 O1 107.29(5) 16 . ? O4 Zn2 O1 107.29(5) . . ? Zn1 O1 Zn1 108.80(8) 2 . ? Zn1 O1 Zn2 109.824(6) 2 . ? Zn1 O1 Zn2 109.823(6) . . ? Zn1 O1 Zn2 109.825(6) 2 2 ? Zn1 O1 Zn2 109.824(6) . 2 ? Zn2 O1 Zn2 108.73(8) . 2 ? C1 O2 Zn1 132.75(15) . . ? C15 O3 Zn1 126.04(12) . 2 ? C15 O4 Zn2 135.43(12) . . ? C14 O5 Zn2 125.0(3) . 3_554 ? O2 C1 O2 121.3(3) . 2 ? O2 C1 C2 119.34(13) . . ? O2 C1 C2 119.34(13) 2 . ? C3 C2 C3 116.2(3) 2 . ? C3 C2 C1 121.89(17) 2 . ? C3 C2 C1 121.89(17) . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 129.3(3) . . ? C5 C4 H4 115.4 . . ? C3 C4 H4 115.4 . . ? C4 C5 C4 105.8(4) 2 . ? C4 C5 C6 127.1(2) 2 . ? C4 C5 C6 127.1(2) . . ? C7 C6 C7 62.0(10) . 16 ? C7 C6 C7 90.6(10) . 15_665 ? C7 C6 C7 122.8(5) 16 15_665 ? C7 C6 C7 122.8(5) . 2 ? C7 C6 C7 90.6(10) 16 2 ? C7 C6 C7 62.0(10) 15_665 2 ? C7 C6 C5 118.6(2) . . ? C7 C6 C5 118.6(2) 16 . ? C7 C6 C5 118.6(2) 15_665 . ? C7 C6 C5 118.6(2) 2 . ? C6 C7 C8 122.0(4) . . ? C6 C7 C7 59.0(5) . 16 ? C8 C7 C7 87.3(5) . 16 ? C6 C7 C8 92.4(4) . 16 ? C8 C7 C8 41.2(5) . 16 ? C7 C7 C8 46.1(3) 16 16 ? C6 C7 C7 44.7(5) . 15_665 ? C8 C7 C7 96.4(5) . 15_665 ? C7 C7 C7 89.999(2) 16 15_665 ? C8 C7 C7 94.6(3) 16 15_665 ? C8 C8 C9 62.4(3) 16 . ? C8 C8 C7 92.7(5) 16 . ? C9 C8 C7 105.7(5) . . ? C8 C8 C7 46.1(3) 16 16 ? C9 C8 C7 81.9(4) . 16 ? C7 C8 C7 46.6(6) . 16 ? C8 C9 C8 109.7(7) . 15_665 ? C8 C9 C8 140.0(6) . 2 ? C8 C9 C8 55.2(7) 15_665 2 ? C8 C9 C8 55.2(7) . 16 ? C8 C9 C8 140.0(6) 15_665 16 ? C8 C9 C8 109.7(7) 2 16 ? C8 C9 C10 110.0(3) . . ? C8 C9 C10 110.0(3) 15_665 . ? C8 C9 C10 110.0(3) 2 . ? C8 C9 C10 110.0(3) 16 . ? C11 C10 C11 123.1(7) 2 . ? C11 C10 C9 118.5(4) 2 . ? C11 C10 C9 118.5(4) . . ? C10 C11 C12 116.9(5) . . ? C10 C11 H11 121.6 . . ? C12 C11 H11 121.6 . . ? C13 C12 C11 125.1(5) . . ? C13 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? C12 C13 C12 113.0(7) . 2 ? C12 C13 C14 123.5(3) . . ? C12 C13 C14 123.5(3) 2 . ? O5 C14 O5 135.6(6) . 2 ? O5 C14 C13 112.2(3) . . ? O5 C14 C13 112.2(3) 2 . ? O3 C15 O4 125.87(16) . . ? O3 C15 C16 118.89(18) . . ? O4 C15 C16 115.23(18) . . ? C17 C16 C21 116.5(2) . . ? C17 C16 C15 127.7(2) . . ? C21 C16 C15 115.6(2) . . ? C16 C17 C18 127.4(2) . . ? C16 C17 H13 116.3 . . ? C18 C17 H13 116.3 . . ? C17 C18 C19 121.5(3) . . ? C17 C18 H14 119.3 . . ? C19 C18 H14 119.3 . . ? C18 C19 C20 115.3(2) . . ? C18 C19 C22 124.0(3) . . ? C20 C19 C22 120.3(3) . . ? C19 C20 C21 122.4(3) . . ? C19 C20 H16 118.8 . . ? C21 C20 H16 118.8 . . ? C16 C21 C20 116.5(3) . . ? C16 C21 H17 121.8 . . ? C20 C21 H17 121.8 . . ? C26 C22 C25 108.4(6) 2_565 2_565 ? C26 C22 C19 129.3(6) 2_565 . ? C25 C22 C19 117.9(5) 2_565 . ? C26 C22 C23 27.6(4) 2_565 . ? C25 C22 C23 127.9(5) 2_565 . ? C19 C22 C23 114.2(3) . . ? C26 C22 C24 118.4(5) 2_565 2_565 ? C25 C22 C24 13.0(3) 2_565 2_565 ? C19 C22 C24 110.7(3) . 2_565 ? C23 C22 C24 133.4(3) . 2_565 ? C26 C23 C24 99.8(4) 2_565 . ? C26 C23 O6 140.6(4) 2_565 . ? C24 C23 O6 114.9(3) . . ? C26 C23 C22 20.9(3) 2_565 . ? C24 C23 C22 115.4(3) . . ? O6 C23 C22 129.5(3) . . ? C25 C24 C23 102.8(4) . . ? C25 C24 O9 138.5(4) . . ? C23 C24 O9 118.5(3) . . ? C25 C24 C26 71.7(4) . 2_565 ? C23 C24 C26 32.0(2) . 2_565 ? O9 C24 C26 149.8(3) . 2_565 ? C25 C24 C22 11.2(3) . 2_565 ? C23 C24 C22 108.9(3) . 2_565 ? O9 C24 C22 130.7(3) . 2_565 ? C26 C24 C22 79.3(2) 2_565 2_565 ? C22 C25 C24 155.8(6) 2_565 . ? C22 C25 C26 32.7(4) 2_565 . ? C24 C25 C26 160.5(5) . . ? C22 C25 C26 119.4(5) 2_565 2_565 ? C24 C25 C26 75.6(4) . 2_565 ? C26 C25 C26 88.1(3) . 2_565 ? C22 C26 C23 131.5(7) 2_565 2_565 ? C22 C26 C25 38.9(4) 2_565 . ? C23 C26 C25 150.9(6) 2_565 . ? C22 C26 C25 127.6(6) 2_565 2_565 ? C23 C26 C25 80.1(4) 2_565 2_565 ? C25 C26 C25 91.7(3) . 2_565 ? C22 C26 C24 150.5(6) 2_565 2_565 ? C23 C26 C24 48.2(3) 2_565 2_565 ? C25 C26 C24 122.6(4) . 2_565 ? C25 C26 C24 32.65(17) 2_565 2_565 ? C28 C27 O6 119.8(5) . . ? C28 C27 H27A 107.4 . . ? O6 C27 H27A 107.4 . . ? C28 C27 H27B 107.4 . . ? O6 C27 H27B 107.4 . . ? H27A C27 H27B 106.9 . . ? C27 C28 O7 103.5(5) . . ? C27 C28 H28A 111.1 . . ? O7 C28 H28A 111.1 . . ? C27 C28 H28B 111.1 . . ? O7 C28 H28B 111.1 . . ? H28A C28 H28B 109.0 . . ? O7 C29 C30 96.2(5) . . ? O7 C29 H29A 112.5 . . ? C30 C29 H29A 112.5 . . ? O7 C29 H29B 112.5 . . ? C30 C29 H29B 112.5 . . ? H29A C29 H29B 110.0 . . ? O8 C30 C29 92.5(4) . . ? O8 C30 H30A 113.2 . . ? C29 C30 H30A 113.2 . . ? O8 C30 H30B 113.2 . . ? C29 C30 H30B 113.2 . . ? H30A C30 H30B 110.6 . . ? O8 C31 C32 126.1(4) . . ? O8 C31 H31A 105.8 . . ? C32 C31 H31A 105.8 . . ? O8 C31 H31B 105.8 . . ? C32 C31 H31B 105.8 . . ? H31A C31 H31B 106.2 . . ? O9 C32 C31 106.5(5) . . ? O9 C32 H32A 110.4 . . ? C31 C32 H32A 110.4 . . ? O9 C32 H32B 110.4 . . ? C31 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C27 O6 C23 114.9(3) . . ? C29 O7 C28 115.0(5) . . ? C30 O8 C31 125.4(5) . . ? C32 O9 C24 126.4(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.60 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.598 _refine_diff_density_min -0.657 _refine_diff_density_rms 0.072 data_mof-bc5 _database_code_depnum_ccdc_archive 'CCDC 883386' #TrackingRef 'web_deposit_cif_file_1_YanliZhao_1352155281.883386.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 15C5 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H24 O13 Zn4' _chemical_formula_weight 1214.27 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Cubic _symmetry_space_group_name_H-M Im-3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'z, x, y' 'z, -x, -y' '-z, -x, y' '-z, x, -y' 'y, z, x' '-y, z, -x' 'y, -z, -x' '-y, -z, x' 'y, x, -z' '-y, -x, -z' 'y, -x, z' '-y, x, z' 'x, z, -y' '-x, z, y' '-x, -z, -y' 'x, -z, y' 'z, y, -x' 'z, -y, x' '-z, y, x' '-z, -y, -x' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'z+1/2, -x+1/2, -y+1/2' '-z+1/2, -x+1/2, y+1/2' '-z+1/2, x+1/2, -y+1/2' 'y+1/2, z+1/2, x+1/2' '-y+1/2, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x+1/2' '-y+1/2, -z+1/2, x+1/2' 'y+1/2, x+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' 'y+1/2, -x+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' 'x+1/2, z+1/2, -y+1/2' '-x+1/2, z+1/2, y+1/2' '-x+1/2, -z+1/2, -y+1/2' 'x+1/2, -z+1/2, y+1/2' 'z+1/2, y+1/2, -x+1/2' 'z+1/2, -y+1/2, x+1/2' '-z+1/2, y+1/2, x+1/2' '-z+1/2, -y+1/2, -x+1/2' '-x, -y, -z' 'x, y, -z' 'x, -y, z' '-x, y, z' '-z, -x, -y' '-z, x, y' 'z, x, -y' 'z, -x, y' '-y, -z, -x' 'y, -z, x' '-y, z, x' 'y, z, -x' '-y, -x, z' 'y, x, z' '-y, x, -z' 'y, -x, -z' '-x, -z, y' 'x, -z, -y' 'x, z, y' '-x, z, -y' '-z, -y, x' '-z, y, -x' 'z, -y, -x' 'z, y, x' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' '-z+1/2, -x+1/2, -y+1/2' '-z+1/2, x+1/2, y+1/2' 'z+1/2, x+1/2, -y+1/2' 'z+1/2, -x+1/2, y+1/2' '-y+1/2, -z+1/2, -x+1/2' 'y+1/2, -z+1/2, x+1/2' '-y+1/2, z+1/2, x+1/2' 'y+1/2, z+1/2, -x+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-x+1/2, -z+1/2, y+1/2' 'x+1/2, -z+1/2, -y+1/2' 'x+1/2, z+1/2, y+1/2' '-x+1/2, z+1/2, -y+1/2' '-z+1/2, -y+1/2, x+1/2' '-z+1/2, y+1/2, -x+1/2' 'z+1/2, -y+1/2, -x+1/2' 'z+1/2, y+1/2, x+1/2' _cell_length_a 21.4744(13) _cell_length_b 21.4744(13) _cell_length_c 21.4744(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9902.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 362 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 23.08 _exptl_crystal_description cube _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8654 _exptl_absorpt_correction_T_max 0.8860 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.013 0.197 0.204 7295 1852 ' ' _platon_squeeze_details ; Very little remaining electron density was left, because of the highly disordered nature of the crown ethers and solvent molecules. The highly diffused electron density makes impossible to locate these atoms. SQUEEZE shows about 1852 electron counts in voids in each unit cell, 636 electrons are from 6 unresolved crown ethers, and 1216 electrons from estimated solvents (about 19 DMF in one unit cell, 9.5 DMF per [Zn4O(C28H26O9)3] )). ; _diffrn_ambient_temperature 153(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_reflns_number 25086 _diffrn_reflns_av_R_equivalents 0.1062 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.16 _reflns_number_total 907 _reflns_number_gt 550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In the structure, 1 ISOR instruction was used to refine.The crystal was weakly diffracting and the structure is extensively disordered, thus the WR2 value is high. The modeled structure formula is C60 H24 O13 Zn4. Including the unresolved crown ethers, and the solvents, the full formula of the structure is [Zn4O(C28H26O9)3].9.5(C7H7NO). ; _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^)+(0.1989P)^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 907 _refine_ls_number_parameters 44 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1460 _refine_ls_R_factor_gt 0.0921 _refine_ls_wR_factor_ref 0.3150 _refine_ls_wR_factor_gt 0.2759 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.129 _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 0.0000 0.0000 1.0000 0.049(3) Uani 1 48 d S . . O2 O 0.0380(3) 0.0380(3) 0.8602(3) 0.107(3) Uani 0.50 2 d SP . . Zn1 Zn 0.05199(5) 0.05199(5) 0.94801(5) 0.0708(9) Uani 0.50 6 d SP . . C1 C 0.0000 0.0000 0.8340(5) 0.104(4) Uani 1 8 d S . . C2 C 0.0000 0.0000 0.7653(5) 0.123(5) Uani 1 8 d S . . C3 C 0.0343(17) 0.040(2) 0.7328(6) 0.203(16) Uani 0.25 1 d P A -1 H3 H 0.0595 0.0681 0.7553 0.243 Uiso 0.25 1 d PR A -1 C4 C 0.0371(5) 0.0371(5) 0.6677(7) 0.175(8) Uani 0.50 2 d SP . . H4 H 0.0653 0.0653 0.6464 0.210 Uiso 0.25 1 d PR A . C5 C 0.0000 0.0000 0.6337(7) 0.173(8) Uani 1 8 d S . . C6 C 0.0000 0.0000 0.5644(9) 0.195(9) Uani 1 8 d S . . C7 C 0.0418(7) 0.0418(7) 0.5337(9) 0.234(11) Uani 0.50 2 d SPU . . 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 0.049(3) 0.049(3) 0.049(3) 0.000 0.000 0.000 O2 0.133(4) 0.133(4) 0.053(4) -0.003(3) -0.003(3) -0.023(4) Zn1 0.0708(9) 0.0708(9) 0.0708(9) 0.0031(5) 0.0031(5) -0.0031(5) C1 0.125(6) 0.125(6) 0.063(7) 0.000 0.000 0.000 C2 0.161(8) 0.161(8) 0.047(7) 0.000 0.000 0.000 C3 0.20(3) 0.35(6) 0.063(8) 0.079(18) -0.062(14) -0.119(18) C4 0.222(13) 0.222(13) 0.082(10) 0.006(6) 0.006(6) -0.073(12) C5 0.229(13) 0.229(13) 0.060(9) 0.000 0.000 0.000 C6 0.235(16) 0.235(16) 0.117(14) 0.000 0.000 0.000 C7 0.275(14) 0.275(14) 0.152(14) 0.035(7) 0.035(7) -0.079(12) _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 Zn1 1.9337(19) 50_557 ? O1 Zn1 1.9337(19) 2 ? O1 Zn1 1.9337(19) 49_557 ? O1 Zn1 1.9337(19) 52 ? O1 Zn1 1.9337(19) 4_557 ? O1 Zn1 1.9337(19) 3_557 ? O1 Zn1 1.9337(19) 51 ? O1 Zn1 1.9338(19) . ? O2 C1 1.283(8) . ? O2 O2 1.632(12) 52 ? O2 O2 1.632(12) 51 ? O2 Zn1 1.934(6) . ? Zn1 O2 1.934(6) 11_566 ? Zn1 O2 1.934(6) 8_656 ? Zn1 Zn1 2.233(2) 51 ? Zn1 Zn1 2.233(2) 52 ? Zn1 Zn1 2.233(2) 50_557 ? Zn1 Zn1 3.158(3) 2 ? Zn1 Zn1 3.158(3) 4_557 ? Zn1 Zn1 3.158(3) 3_557 ? C1 O2 1.283(8) 2 ? C1 O2 1.283(8) 52 ? C1 O2 1.283(8) 51 ? C1 C2 1.475(15) . ? C2 C3 1.325(16) . ? C2 C3 1.325(16) 61 ? C2 C3 1.325(16) 2 ? C2 C3 1.325(16) 16 ? C2 C3 1.325(16) 62 ? C2 C3 1.325(16) 51 ? C2 C3 1.325(16) 15 ? C2 C3 1.325(16) 52 ? C3 C4 1.40(2) . ? C3 H3 0.9500 . ? C4 C5 1.343(15) . ? C4 C3 1.40(2) 62 ? C4 C4 1.59(2) 52 ? C4 C4 1.59(2) 51 ? C4 H4 0.9690 . ? C5 C4 1.343(15) 2 ? C5 C4 1.343(15) 52 ? C5 C4 1.343(15) 51 ? C5 C6 1.49(2) . ? C6 C7 1.429(18) . ? C6 C7 1.429(18) 2 ? C6 C7 1.429(18) 52 ? C6 C7 1.429(18) 51 ? C7 C7 1.45(4) 50_556 ? C7 C7 1.79(3) 52 ? C7 C7 1.79(3) 51 ? 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 Zn1 O1 Zn1 180.0 50_557 2 ? Zn1 O1 Zn1 109.471(1) 50_557 49_557 ? Zn1 O1 Zn1 70.529(1) 2 49_557 ? Zn1 O1 Zn1 109.471(1) 50_557 52 ? Zn1 O1 Zn1 70.529(1) 2 52 ? Zn1 O1 Zn1 109.5 49_557 52 ? Zn1 O1 Zn1 70.529(1) 50_557 4_557 ? Zn1 O1 Zn1 109.5 2 4_557 ? Zn1 O1 Zn1 70.529(1) 49_557 4_557 ? Zn1 O1 Zn1 180.00(5) 52 4_557 ? Zn1 O1 Zn1 70.529(1) 50_557 3_557 ? Zn1 O1 Zn1 109.5 2 3_557 ? Zn1 O1 Zn1 70.529(1) 49_557 3_557 ? Zn1 O1 Zn1 70.529(1) 52 3_557 ? Zn1 O1 Zn1 109.471(1) 4_557 3_557 ? Zn1 O1 Zn1 109.471(1) 50_557 51 ? Zn1 O1 Zn1 70.529(1) 2 51 ? Zn1 O1 Zn1 109.5 49_557 51 ? Zn1 O1 Zn1 109.471(1) 52 51 ? Zn1 O1 Zn1 70.529(1) 4_557 51 ? Zn1 O1 Zn1 180.00(5) 3_557 51 ? Zn1 O1 Zn1 70.5 50_557 . ? Zn1 O1 Zn1 109.5 2 . ? Zn1 O1 Zn1 180.0 49_557 . ? Zn1 O1 Zn1 70.5 52 . ? Zn1 O1 Zn1 109.471(1) 4_557 . ? Zn1 O1 Zn1 109.471(1) 3_557 . ? Zn1 O1 Zn1 70.5 51 . ? C1 O2 O2 50.5(2) . 52 ? C1 O2 O2 50.5(2) . 51 ? O2 O2 O2 89.996(1) 52 51 ? C1 O2 Zn1 128.7(8) . . ? O2 O2 Zn1 98.94(18) 52 . ? O2 O2 Zn1 98.94(18) 51 . ? O2 Zn1 O2 106.2(3) . 11_566 ? O2 Zn1 O2 106.2(3) . 8_656 ? O2 Zn1 O2 106.2(3) 11_566 8_656 ? O2 Zn1 O1 112.6(3) . . ? O2 Zn1 O1 112.6(3) 11_566 . ? O2 Zn1 O1 112.6(3) 8_656 . ? O2 Zn1 Zn1 81.06(18) . 51 ? O2 Zn1 Zn1 167.3(3) 11_566 51 ? O2 Zn1 Zn1 81.06(18) 8_656 51 ? O1 Zn1 Zn1 54.7 . 51 ? O2 Zn1 Zn1 81.06(18) . 52 ? O2 Zn1 Zn1 81.06(18) 11_566 52 ? O2 Zn1 Zn1 167.3(3) 8_656 52 ? O1 Zn1 Zn1 54.733(1) . 52 ? Zn1 Zn1 Zn1 89.996(1) 51 52 ? O2 Zn1 Zn1 167.3(3) . 50_557 ? O2 Zn1 Zn1 81.06(18) 11_566 50_557 ? O2 Zn1 Zn1 81.06(18) 8_656 50_557 ? O1 Zn1 Zn1 54.7 . 50_557 ? Zn1 Zn1 Zn1 89.996(1) 51 50_557 ? Zn1 Zn1 Zn1 89.996(1) 52 50_557 ? O2 Zn1 Zn1 77.3(3) . 2 ? O2 Zn1 Zn1 125.4(2) 11_566 2 ? O2 Zn1 Zn1 125.4(2) 8_656 2 ? O1 Zn1 Zn1 35.3 . 2 ? Zn1 Zn1 Zn1 45.0 51 2 ? Zn1 Zn1 Zn1 45.0 52 2 ? Zn1 Zn1 Zn1 89.996(1) 50_557 2 ? O2 Zn1 Zn1 125.4(2) . 4_557 ? O2 Zn1 Zn1 125.4(2) 11_566 4_557 ? O2 Zn1 Zn1 77.3(3) 8_656 4_557 ? O1 Zn1 Zn1 35.3 . 4_557 ? Zn1 Zn1 Zn1 44.998(1) 51 4_557 ? Zn1 Zn1 Zn1 89.996(1) 52 4_557 ? Zn1 Zn1 Zn1 45.0 50_557 4_557 ? Zn1 Zn1 Zn1 59.998(1) 2 4_557 ? O2 Zn1 Zn1 125.4(2) . 3_557 ? O2 Zn1 Zn1 77.3(3) 11_566 3_557 ? O2 Zn1 Zn1 125.4(2) 8_656 3_557 ? O1 Zn1 Zn1 35.3 . 3_557 ? Zn1 Zn1 Zn1 89.996(1) 51 3_557 ? Zn1 Zn1 Zn1 44.998(1) 52 3_557 ? Zn1 Zn1 Zn1 45.0 50_557 3_557 ? Zn1 Zn1 Zn1 59.998(1) 2 3_557 ? Zn1 Zn1 Zn1 60.0 4_557 3_557 ? O2 C1 O2 79.0(5) 2 52 ? O2 C1 O2 79.0(5) 2 51 ? O2 C1 O2 128.1(12) 52 51 ? O2 C1 O2 128.1(12) 2 . ? O2 C1 O2 79.0(5) 52 . ? O2 C1 O2 79.0(5) 51 . ? O2 C1 C2 116.0(6) 2 . ? O2 C1 C2 116.0(6) 52 . ? O2 C1 C2 116.0(6) 51 . ? O2 C1 C2 116.0(6) . . ? C3 C2 C3 115.8(15) . 61 ? C3 C2 C3 116.2(17) . 2 ? C3 C2 C3 7(5) 61 2 ? C3 C2 C3 73.8(8) . 16 ? C3 C2 C3 67(4) 61 16 ? C3 C2 C3 73.8(8) 2 16 ? C3 C2 C3 7(5) . 62 ? C3 C2 C3 116.2(17) 61 62 ? C3 C2 C3 115.8(15) 2 62 ? C3 C2 C3 80(5) 16 62 ? C3 C2 C3 80(5) . 51 ? C3 C2 C3 73.8(8) 61 51 ? C3 C2 C3 67(4) 2 51 ? C3 C2 C3 115.8(15) 16 51 ? C3 C2 C3 73.8(8) 62 51 ? C3 C2 C3 73.8(8) . 15 ? C3 C2 C3 80(5) 61 15 ? C3 C2 C3 73.8(8) 2 15 ? C3 C2 C3 116.2(17) 16 15 ? C3 C2 C3 67(4) 62 15 ? C3 C2 C3 7(5) 51 15 ? C3 C2 C3 67(4) . 52 ? C3 C2 C3 73.8(8) 61 52 ? C3 C2 C3 80(5) 2 52 ? C3 C2 C3 7(5) 16 52 ? C3 C2 C3 73.8(8) 62 52 ? C3 C2 C3 116.2(17) 51 52 ? C3 C2 C3 115.8(15) 15 52 ? C3 C2 C1 121.9(8) . . ? C3 C2 C1 121.9(8) 61 . ? C3 C2 C1 121.9(8) 2 . ? C3 C2 C1 121.9(8) 16 . ? C3 C2 C1 121.9(8) 62 . ? C3 C2 C1 121.9(8) 51 . ? C3 C2 C1 121.9(8) 15 . ? C3 C2 C1 121.9(8) 52 . ? C2 C3 C4 121.8(17) . . ? C2 C3 H3 117.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 122.6(14) . . ? C5 C4 C3 122.6(14) . 62 ? C3 C4 C3 7(5) . 62 ? C5 C4 C4 53.6(4) . 52 ? C3 C4 C4 87.5(16) . 52 ? C3 C4 C4 92.2(19) 62 52 ? C5 C4 C4 53.6(4) . 51 ? C3 C4 C4 92.2(19) . 51 ? C3 C4 C4 87.5(16) 62 51 ? C4 C4 C4 89.997(2) 52 51 ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.3 . . ? C3 C4 H4 118.3 62 . ? C4 C4 H4 128.6 52 . ? C4 C4 H4 128.6 51 . ? C4 C5 C4 72.8(8) 2 52 ? C4 C5 C4 72.8(8) 2 51 ? C4 C5 C4 114.1(17) 52 51 ? C4 C5 C4 114.1(17) 2 . ? C4 C5 C4 72.8(8) 52 . ? C4 C5 C4 72.8(8) 51 . ? C4 C5 C6 122.9(8) 2 . ? C4 C5 C6 122.9(8) 52 . ? C4 C5 C6 122.9(8) 51 . ? C4 C5 C6 122.9(8) . . ? C7 C6 C7 125(2) . 2 ? C7 C6 C7 77.7(10) . 52 ? C7 C6 C7 77.7(10) 2 52 ? C7 C6 C7 77.7(10) . 51 ? C7 C6 C7 77.7(10) 2 51 ? C7 C6 C7 125(2) 52 51 ? C7 C6 C5 117.5(12) . . ? C7 C6 C5 117.5(12) 2 . ? C7 C6 C5 117.5(12) 52 . ? C7 C6 C5 117.5(12) 51 . ? C6 C7 C7 117.5(12) . 50_556 ? C6 C7 C7 51.1(5) . 52 ? C7 C7 C7 90.002(4) 50_556 52 ? C6 C7 C7 51.1(5) . 51 ? C7 C7 C7 90.002(1) 50_556 51 ? C7 C7 C7 90.004(2) 52 51 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.365 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.053