# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kristopher V. Waynant' _publ_contact_author_email kwaynant@gmail.com loop_ _publ_author_name 'Kristopher V. Waynant' 'James D. White' 'Lev Zakharov' data_jw56 _database_code_depnum_ccdc_archive 'CCDC 774941' #TrackingRef '10-jw56.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Ba Cl2 O18' _chemical_formula_weight 756.60 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ba Ba -0.3244 2.2819 '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 10.1152(15) _cell_length_b 10.2248(15) _cell_length_c 12.9429(19) _cell_angle_alpha 92.527(2) _cell_angle_beta 99.751(2) _cell_angle_gamma 97.818(2) _cell_volume 1303.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6100 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 28.23 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5379 _exptl_absorpt_correction_T_max 0.8684 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14739 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5654 _reflns_number_gt 5528 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0380P)^2^+0.4783P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5654 _refine_ls_number_parameters 479 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0209 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0639 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.190 _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 Ba1 Ba 0.239542(11) 0.773093(10) 0.524987(9) 0.02264(5) Uani 1 1 d . . . Cl1 Cl 0.06692(5) 1.07478(5) 0.64521(4) 0.02708(11) Uani 1 1 d . . . Cl2 Cl 0.36111(6) 0.76846(6) 0.82572(5) 0.03689(13) Uani 1 1 d D . . O1 O 0.11671(18) 0.60899(16) 0.34771(12) 0.0337(4) Uani 1 1 d . A . O2 O 0.32574(15) 0.82588(18) 0.33866(13) 0.0348(4) Uani 1 1 d . A . O3 O -0.04187(16) 0.70043(15) 0.05556(12) 0.0306(3) Uani 1 1 d . A . O4 O 0.10830(16) 0.87017(15) 0.05223(12) 0.0276(3) Uani 1 1 d . A . O5 O 0.50953(17) 0.74697(18) 0.53723(14) 0.0374(4) Uani 1 1 d . A . O6 O 0.31314(17) 0.52354(16) 0.55145(13) 0.0334(4) Uani 1 1 d . A . O7 O 0.74449(15) 0.59766(15) 0.77560(12) 0.0267(3) Uani 1 1 d . A . O8 O 0.59290(15) 0.43366(15) 0.79198(12) 0.0274(3) Uani 1 1 d . A . O9 O 0.09783(17) 0.94375(16) 0.62778(13) 0.0330(3) Uani 1 1 d . A . O10 O -0.07774(16) 1.07279(18) 0.61880(13) 0.0362(4) Uani 1 1 d . . . O11 O 0.11250(19) 1.1195(2) 0.75360(14) 0.0465(5) Uani 1 1 d . A . O12 O 0.1335(2) 1.16236(18) 0.57943(17) 0.0470(5) Uani 1 1 d . A . O13 O 0.2687(13) 0.6904(13) 0.7428(9) 0.069(3) Uani 0.609(17) 1 d PD A 1 O14 O 0.4060(5) 0.9049(5) 0.8151(10) 0.076(3) Uani 0.609(17) 1 d PD A 1 O15 O 0.2715(6) 0.7681(6) 0.9032(6) 0.0488(14) Uani 0.609(17) 1 d PD A 1 O16 O 0.4760(14) 0.7070(16) 0.8681(15) 0.047(3) Uani 0.609(17) 1 d PD A 1 O13A O 0.2854(16) 0.6990(17) 0.7326(9) 0.052(4) Uani 0.391(17) 1 d PD A 2 O14A O 0.4209(10) 0.8528(15) 0.7501(10) 0.081(5) Uani 0.391(17) 1 d PD A 2 O15A O 0.300(2) 0.821(2) 0.8970(11) 0.136(8) Uani 0.391(17) 1 d PD A 2 O16A O 0.455(2) 0.681(2) 0.8653(19) 0.037(4) Uani 0.391(17) 1 d PD A 2 O17 O 0.3883(2) 1.02105(18) 0.56596(16) 0.0476(5) Uani 1 1 d . A . O18 O -0.00639(18) 0.6344(2) 0.55616(15) 0.0346(4) Uani 1 1 d . A . C1 C -0.2293(4) 0.5319(3) 0.0307(3) 0.0529(8) Uani 1 1 d . . . C2 C -0.1039(3) 0.5950(2) 0.10157(19) 0.0339(5) Uani 1 1 d . . . C3 C -0.0504(3) 0.5630(2) 0.19679(18) 0.0331(5) Uani 1 1 d . A . C4 C 0.0724(2) 0.6363(2) 0.25787(17) 0.0270(4) Uani 1 1 d . . . C5 C 0.1357(2) 0.7459(2) 0.20532(16) 0.0236(4) Uani 1 1 d . A . C6 C 0.0712(2) 0.7705(2) 0.10907(17) 0.0240(4) Uani 1 1 d . . . C7 C 0.2581(2) 0.8371(2) 0.25199(17) 0.0269(4) Uani 1 1 d . . . C8 C 0.2951(2) 0.9431(2) 0.18704(18) 0.0294(4) Uani 1 1 d . A . C9 C 0.2240(2) 0.9574(2) 0.09307(18) 0.0271(4) Uani 1 1 d . . . C10 C 0.2510(3) 1.0606(3) 0.0192(2) 0.0368(5) Uani 1 1 d . A . C11 C 0.9316(3) 0.7662(3) 0.7864(2) 0.0349(5) Uani 1 1 d . . . C12 C 0.7940(2) 0.7103(2) 0.73128(17) 0.0268(4) Uani 1 1 d . . . C13 C 0.7192(2) 0.7575(2) 0.64969(18) 0.0294(4) Uani 1 1 d . A . C14 C 0.5820(2) 0.6967(2) 0.60663(17) 0.0277(4) Uani 1 1 d . . . C15 C 0.5352(2) 0.5755(2) 0.65354(16) 0.0233(4) Uani 1 1 d . A . C16 C 0.6202(2) 0.5366(2) 0.73557(16) 0.0238(4) Uani 1 1 d . . . C17 C 0.4001(2) 0.4977(2) 0.62372(17) 0.0259(4) Uani 1 1 d . . . C18 C 0.3743(2) 0.3875(2) 0.68749(18) 0.0297(4) Uani 1 1 d . A . C19 C 0.4653(2) 0.3596(2) 0.76706(18) 0.0281(4) Uani 1 1 d . . . C20 C 0.4481(3) 0.2539(3) 0.8413(2) 0.0388(6) Uani 1 1 d . A . H1A H -0.281(4) 0.467(4) 0.052(3) 0.072(12) Uiso 1 1 d . . . H1B H -0.204(4) 0.492(4) -0.030(3) 0.066(11) Uiso 1 1 d . . . H1C H -0.283(4) 0.604(4) -0.003(3) 0.077(12) Uiso 1 1 d . . . H3 H -0.099(3) 0.490(3) 0.225(3) 0.052(9) Uiso 1 1 d . . . H8 H 0.368(3) 0.998(3) 0.209(2) 0.030(7) Uiso 1 1 d . . . H10A H 0.264(4) 1.026(4) -0.036(3) 0.074(13) Uiso 1 1 d . . . H10B H 0.178(4) 1.106(4) 0.001(3) 0.070(11) Uiso 1 1 d . . . H10C H 0.328(3) 1.122(3) 0.049(3) 0.050(9) Uiso 1 1 d . . . H11A H 0.990(5) 0.720(5) 0.780(4) 0.086(15) Uiso 1 1 d . . . H11B H 0.956(4) 0.851(4) 0.783(3) 0.078(13) Uiso 1 1 d . . . H11C H 0.935(5) 0.767(5) 0.863(4) 0.092(15) Uiso 1 1 d . . . H13 H 0.762(3) 0.840(3) 0.619(2) 0.037(7) Uiso 1 1 d . . . H18 H 0.290(3) 0.336(3) 0.675(2) 0.035(7) Uiso 1 1 d . . . H20A H 0.506(4) 0.207(4) 0.847(3) 0.072(12) Uiso 1 1 d . . . H20B H 0.355(4) 0.213(3) 0.831(3) 0.055(9) Uiso 1 1 d . . . H20C H 0.476(4) 0.297(4) 0.921(3) 0.071(11) Uiso 1 1 d . . . H1O H -0.031(4) 0.561(5) 0.571(3) 0.076(13) Uiso 1 1 d . . . H2O H -0.063(4) 0.659(4) 0.522(3) 0.056(11) Uiso 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 Ba1 0.02412(8) 0.02062(8) 0.02382(8) 0.00361(5) 0.00629(5) 0.00238(5) Cl1 0.0269(2) 0.0251(2) 0.0281(3) -0.00226(19) 0.00026(19) 0.00705(19) Cl2 0.0334(3) 0.0353(3) 0.0406(3) 0.0055(2) 0.0036(2) 0.0028(2) O1 0.0495(10) 0.0275(8) 0.0231(8) 0.0064(6) 0.0038(7) 0.0043(7) O2 0.0241(7) 0.0535(10) 0.0272(8) 0.0089(7) 0.0037(6) 0.0058(7) O3 0.0356(8) 0.0279(8) 0.0251(7) 0.0060(6) 0.0003(6) -0.0020(6) O4 0.0308(8) 0.0267(7) 0.0254(7) 0.0074(6) 0.0056(6) 0.0020(6) O5 0.0317(8) 0.0429(10) 0.0403(9) 0.0226(8) 0.0059(7) 0.0091(7) O6 0.0354(8) 0.0279(8) 0.0334(8) 0.0023(6) -0.0063(7) 0.0072(6) O7 0.0241(7) 0.0297(8) 0.0263(7) 0.0072(6) 0.0040(6) 0.0022(6) O8 0.0252(7) 0.0272(7) 0.0299(8) 0.0100(6) 0.0031(6) 0.0035(6) O9 0.0380(9) 0.0259(8) 0.0394(9) 0.0032(7) 0.0136(7) 0.0113(7) O10 0.0269(8) 0.0451(10) 0.0355(9) -0.0050(7) -0.0023(7) 0.0138(7) O11 0.0401(10) 0.0631(12) 0.0328(9) -0.0161(8) -0.0084(8) 0.0203(9) O12 0.0522(11) 0.0297(9) 0.0551(12) 0.0096(8) 0.0068(9) -0.0070(8) O13 0.059(4) 0.076(5) 0.062(6) -0.003(4) -0.010(4) 0.000(4) O14 0.055(2) 0.036(2) 0.142(8) 0.017(3) 0.038(3) -0.0059(17) O15 0.051(3) 0.054(3) 0.047(2) -0.004(2) 0.0186(17) 0.019(2) O16 0.032(4) 0.059(6) 0.045(4) -0.011(4) -0.009(3) 0.011(5) O13A 0.060(6) 0.090(9) 0.011(3) -0.012(4) -0.005(3) 0.051(7) O14A 0.062(5) 0.087(8) 0.077(7) 0.047(6) -0.010(4) -0.035(5) O15A 0.232(17) 0.146(16) 0.050(6) -0.039(8) 0.004(8) 0.139(13) O16A 0.031(6) 0.050(7) 0.030(6) 0.011(6) 0.004(4) 0.006(5) O17 0.0539(11) 0.0303(9) 0.0554(12) 0.0057(8) 0.0121(9) -0.0089(8) O18 0.0275(8) 0.0365(10) 0.0396(10) 0.0082(8) 0.0060(7) 0.0017(7) C1 0.0618(19) 0.0438(16) 0.0393(15) 0.0088(13) -0.0086(14) -0.0215(15) C2 0.0433(13) 0.0251(10) 0.0298(11) 0.0031(9) 0.0049(10) -0.0057(9) C3 0.0449(13) 0.0227(10) 0.0295(11) 0.0036(8) 0.0055(10) -0.0024(9) C4 0.0371(11) 0.0215(10) 0.0249(10) 0.0035(8) 0.0094(9) 0.0076(8) C5 0.0258(10) 0.0248(10) 0.0218(9) 0.0038(8) 0.0067(8) 0.0063(8) C6 0.0283(10) 0.0211(9) 0.0239(10) 0.0025(8) 0.0078(8) 0.0043(8) C7 0.0234(10) 0.0342(11) 0.0257(10) 0.0027(8) 0.0082(8) 0.0079(8) C8 0.0243(10) 0.0306(11) 0.0333(11) 0.0014(9) 0.0079(9) 0.0006(9) C9 0.0274(10) 0.0246(10) 0.0314(11) 0.0029(8) 0.0111(8) 0.0031(8) C10 0.0426(14) 0.0293(12) 0.0408(14) 0.0111(11) 0.0132(11) 0.0036(11) C11 0.0299(12) 0.0402(14) 0.0328(13) 0.0053(10) 0.0063(10) -0.0040(10) C12 0.0282(10) 0.0269(10) 0.0270(10) 0.0028(8) 0.0106(8) 0.0022(8) C13 0.0301(11) 0.0299(11) 0.0300(11) 0.0082(9) 0.0091(9) 0.0035(9) C14 0.0301(11) 0.0305(11) 0.0257(10) 0.0067(8) 0.0090(8) 0.0087(9) C15 0.0259(10) 0.0243(10) 0.0214(9) 0.0034(7) 0.0058(8) 0.0073(8) C16 0.0252(10) 0.0235(10) 0.0242(10) 0.0038(8) 0.0071(8) 0.0046(8) C17 0.0302(10) 0.0215(9) 0.0255(10) -0.0016(8) 0.0028(8) 0.0061(8) C18 0.0272(10) 0.0251(10) 0.0349(12) 0.0027(9) 0.0017(9) 0.0016(8) C19 0.0273(10) 0.0237(10) 0.0341(11) 0.0053(8) 0.0073(9) 0.0036(8) C20 0.0325(13) 0.0370(13) 0.0490(16) 0.0208(12) 0.0085(11) 0.0054(11) _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 Ba1 O17 2.7472(18) . ? Ba1 O2 2.7507(16) . ? Ba1 O5 2.7586(17) . ? Ba1 O6 2.7731(16) . ? Ba1 O1 2.7842(16) . ? Ba1 O18 2.7917(18) . ? Ba1 O13A 2.804(15) . ? Ba1 O9 2.8269(16) . ? Ba1 O10 2.9247(17) 2_576 ? Ba1 O13 2.958(13) . ? Ba1 O14A 3.177(10) . ? Cl1 O9 1.4335(16) . ? Cl1 O11 1.4341(18) . ? Cl1 O12 1.442(2) . ? Cl1 O10 1.4423(16) . ? Cl2 O15A 1.322(11) . ? Cl2 O16 1.435(11) . ? Cl2 O13A 1.417(11) . ? Cl2 O14 1.427(4) . ? Cl2 O13 1.430(10) . ? Cl2 O15 1.461(5) . ? Cl2 O14A 1.483(7) . ? Cl2 O16A 1.438(16) . ? O1 C4 1.232(3) . ? O2 C7 1.230(3) . ? O3 C6 1.329(3) . ? O3 C2 1.382(3) . ? O4 C6 1.332(3) . ? O4 C9 1.382(3) . ? O5 C14 1.237(3) . ? O6 C17 1.235(3) . ? O7 C16 1.332(3) . ? O7 C12 1.381(3) . ? O8 C16 1.332(2) . ? O8 C19 1.384(3) . ? O10 Ba1 2.9247(17) 2_576 ? O18 H1O 0.80(5) . ? O18 H2O 0.74(4) . ? C1 C2 1.483(4) . ? C1 H1A 0.87(4) . ? C1 H1B 0.95(4) . ? C1 H1C 1.04(4) . ? C2 C3 1.333(3) . ? C3 C4 1.446(3) . ? C3 H3 0.96(3) . ? C4 C5 1.465(3) . ? C5 C6 1.356(3) . ? C5 C7 1.466(3) . ? C7 C8 1.448(3) . ? C8 C9 1.329(3) . ? C8 H8 0.86(3) . ? C9 C10 1.484(3) . ? C10 H10A 0.82(4) . ? C10 H10B 0.93(4) . ? C10 H10C 0.94(3) . ? C11 C12 1.478(3) . ? C11 H11A 0.81(5) . ? C11 H11B 0.87(4) . ? C11 H11C 0.99(5) . ? C12 C13 1.339(3) . ? C13 C14 1.447(3) . ? C13 H13 1.02(3) . ? C14 C15 1.461(3) . ? C15 C16 1.359(3) . ? C15 C17 1.466(3) . ? C17 C18 1.447(3) . ? C18 C19 1.328(3) . ? C18 H18 0.92(3) . ? C19 C20 1.489(3) . ? C20 H20A 0.80(4) . ? C20 H20B 0.96(4) . ? C20 H20C 1.08(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O17 Ba1 O2 76.35(6) . . ? O17 Ba1 O5 72.07(6) . . ? O2 Ba1 O5 68.78(5) . . ? O17 Ba1 O6 131.36(6) . . ? O2 Ba1 O6 100.06(5) . . ? O5 Ba1 O6 62.04(5) . . ? O17 Ba1 O1 136.81(5) . . ? O2 Ba1 O1 62.45(5) . . ? O5 Ba1 O1 102.41(6) . . ? O6 Ba1 O1 71.59(5) . . ? O17 Ba1 O18 139.93(6) . . ? O2 Ba1 O18 128.62(5) . . ? O5 Ba1 O18 141.41(6) . . ? O6 Ba1 O18 79.99(6) . . ? O1 Ba1 O18 69.34(5) . . ? O17 Ba1 O13A 96.1(4) . . ? O2 Ba1 O13A 151.5(3) . . ? O5 Ba1 O13A 82.8(3) . . ? O6 Ba1 O13A 64.2(3) . . ? O1 Ba1 O13A 126.3(3) . . ? O18 Ba1 O13A 74.3(4) . . ? O17 Ba1 O9 69.58(6) . . ? O2 Ba1 O9 123.10(5) . . ? O5 Ba1 O9 134.27(5) . . ? O6 Ba1 O9 136.64(5) . . ? O1 Ba1 O9 122.54(5) . . ? O18 Ba1 O9 70.36(5) . . ? O13A Ba1 O9 77.5(3) . . ? O17 Ba1 O10 78.66(6) . 2_576 ? O2 Ba1 O10 62.91(5) . 2_576 ? O5 Ba1 O10 127.92(5) . 2_576 ? O6 Ba1 O10 143.36(5) . 2_576 ? O1 Ba1 O10 71.78(5) . 2_576 ? O18 Ba1 O10 86.59(6) . 2_576 ? O13A Ba1 O10 143.4(3) . 2_576 ? O9 Ba1 O10 66.60(5) . 2_576 ? O17 Ba1 O13 98.3(2) . . ? O2 Ba1 O13 155.0(3) . . ? O5 Ba1 O13 86.3(3) . . ? O6 Ba1 O13 64.8(2) . . ? O1 Ba1 O13 124.5(2) . . ? O18 Ba1 O13 70.7(2) . . ? O13A Ba1 O13 3.7(6) . . ? O9 Ba1 O13 75.7(2) . . ? O10 Ba1 O13 140.8(3) 2_576 . ? O17 Ba1 O14A 60.33(17) . . ? O2 Ba1 O14A 123.98(18) . . ? O5 Ba1 O14A 65.4(3) . . ? O6 Ba1 O14A 85.6(3) . . ? O1 Ba1 O14A 157.2(3) . . ? O18 Ba1 O14A 107.34(17) . . ? O13A Ba1 O14A 36.8(4) . . ? O9 Ba1 O14A 74.4(4) . . ? O10 Ba1 O14A 131.1(3) 2_576 . ? O13 Ba1 O14A 39.7(3) . . ? O9 Cl1 O11 109.61(11) . . ? O9 Cl1 O12 109.29(11) . . ? O11 Cl1 O12 109.91(13) . . ? O9 Cl1 O10 109.11(10) . . ? O11 Cl1 O10 109.45(11) . . ? O12 Cl1 O10 109.45(12) . . ? O15A Cl2 O16 114.6(10) . . ? O15A Cl2 O13A 121.3(12) . . ? O16 Cl2 O13A 112.1(9) . . ? O15A Cl2 O14 81.4(10) . . ? O16 Cl2 O14 108.8(8) . . ? O13A Cl2 O14 114.5(10) . . ? O15A Cl2 O13 113.3(13) . . ? O16 Cl2 O13 114.2(9) . . ? O13A Cl2 O13 9.7(13) . . ? O14 Cl2 O13 120.7(8) . . ? O15A Cl2 O15 23.8(12) . . ? O16 Cl2 O15 108.4(8) . . ? O13A Cl2 O15 107.5(8) . . ? O14 Cl2 O15 105.1(4) . . ? O13 Cl2 O15 98.1(6) . . ? O15A Cl2 O14A 120.5(9) . . ? O16 Cl2 O14A 100.1(8) . . ? O13A Cl2 O14A 82.8(10) . . ? O14 Cl2 O14A 40.9(5) . . ? O13 Cl2 O14A 91.8(8) . . ? O15 Cl2 O14A 142.4(8) . . ? O15A Cl2 O16A 114.9(13) . . ? O16 Cl2 O16A 12.5(16) . . ? O13A Cl2 O16A 103.7(12) . . ? O14 Cl2 O16A 121.2(11) . . ? O13 Cl2 O16A 104.2(12) . . ? O15 Cl2 O16A 103.7(10) . . ? O14A Cl2 O16A 108.8(11) . . ? C4 O1 Ba1 130.44(14) . . ? C7 O2 Ba1 129.07(14) . . ? C6 O3 C2 118.51(17) . . ? C6 O4 C9 118.13(17) . . ? C14 O5 Ba1 127.55(14) . . ? C17 O6 Ba1 124.16(13) . . ? C16 O7 C12 118.56(17) . . ? C16 O8 C19 117.78(17) . . ? Cl1 O9 Ba1 148.38(10) . . ? Cl1 O10 Ba1 131.12(11) . 2_576 ? Cl2 O13 Ba1 120.4(8) . . ? Cl2 O13A Ba1 130.9(11) . . ? Cl2 O14A Ba1 107.2(4) . . ? Ba1 O18 H1O 135(3) . . ? Ba1 O18 H2O 109(3) . . ? H1O O18 H2O 110(4) . . ? C2 C1 H1A 120(3) . . ? C2 C1 H1B 108(2) . . ? H1A C1 H1B 103(3) . . ? C2 C1 H1C 110(2) . . ? H1A C1 H1C 113(3) . . ? H1B C1 H1C 101(3) . . ? C3 C2 O3 120.8(2) . . ? C3 C2 C1 129.0(2) . . ? O3 C2 C1 110.2(2) . . ? C2 C3 C4 122.7(2) . . ? C2 C3 H3 117.2(19) . . ? C4 C3 H3 120.1(19) . . ? O1 C4 C3 121.7(2) . . ? O1 C4 C5 123.7(2) . . ? C3 C4 C5 114.65(19) . . ? C6 C5 C4 117.5(2) . . ? C6 C5 C7 117.31(19) . . ? C4 C5 C7 125.00(19) . . ? O3 C6 O4 107.93(18) . . ? O3 C6 C5 125.80(19) . . ? O4 C6 C5 126.3(2) . . ? O2 C7 C8 121.7(2) . . ? O2 C7 C5 123.8(2) . . ? C8 C7 C5 114.48(19) . . ? C9 C8 C7 123.0(2) . . ? C9 C8 H8 117.6(18) . . ? C7 C8 H8 119.3(18) . . ? C8 C9 O4 120.8(2) . . ? C8 C9 C10 128.2(2) . . ? O4 C9 C10 111.0(2) . . ? C9 C10 H10A 110(3) . . ? C9 C10 H10B 112(2) . . ? H10A C10 H10B 106(4) . . ? C9 C10 H10C 110(2) . . ? H10A C10 H10C 109(4) . . ? H10B C10 H10C 109(3) . . ? C12 C11 H11A 115(3) . . ? C12 C11 H11B 116(3) . . ? H11A C11 H11B 116(4) . . ? C12 C11 H11C 110(3) . . ? H11A C11 H11C 100(4) . . ? H11B C11 H11C 97(4) . . ? C13 C12 O7 120.9(2) . . ? C13 C12 C11 127.8(2) . . ? O7 C12 C11 111.32(19) . . ? C12 C13 C14 122.1(2) . . ? C12 C13 H13 117.4(16) . . ? C14 C13 H13 120.5(16) . . ? O5 C14 C13 121.7(2) . . ? O5 C14 C15 123.1(2) . . ? C13 C14 C15 115.19(19) . . ? C16 C15 C14 117.44(19) . . ? C16 C15 C17 117.44(19) . . ? C14 C15 C17 124.98(19) . . ? O7 C16 O8 108.05(17) . . ? O7 C16 C15 125.71(19) . . ? O8 C16 C15 126.22(19) . . ? O6 C17 C18 121.8(2) . . ? O6 C17 C15 123.7(2) . . ? C18 C17 C15 114.52(18) . . ? C19 C18 C17 122.8(2) . . ? C19 C18 H18 117.9(17) . . ? C17 C18 H18 119.3(17) . . ? C18 C19 O8 121.22(19) . . ? C18 C19 C20 127.7(2) . . ? O8 C19 C20 111.10(19) . . ? C19 C20 H20A 114(3) . . ? C19 C20 H20B 110(2) . . ? H20A C20 H20B 119(4) . . ? C19 C20 H20C 109(2) . . ? H20A C20 H20C 95(3) . . ? H20B C20 H20C 108(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O17 Ba1 O1 C4 -26.7(2) . . . . ? O2 Ba1 O1 C4 -45.83(19) . . . . ? O5 Ba1 O1 C4 -103.6(2) . . . . ? O6 Ba1 O1 C4 -158.2(2) . . . . ? O18 Ba1 O1 C4 115.8(2) . . . . ? O13A Ba1 O1 C4 166.3(4) . . . . ? O9 Ba1 O1 C4 67.6(2) . . . . ? O10 Ba1 O1 C4 22.52(19) 2_576 . . . ? O13 Ba1 O1 C4 162.3(4) . . . . ? O14A Ba1 O1 C4 -158.5(6) . . . . ? O17 Ba1 O2 C7 -116.9(2) . . . . ? O5 Ba1 O2 C7 167.3(2) . . . . ? O6 Ba1 O2 C7 112.7(2) . . . . ? O1 Ba1 O2 C7 49.7(2) . . . . ? O18 Ba1 O2 C7 27.5(2) . . . . ? O13A Ba1 O2 C7 165.8(7) . . . . ? O9 Ba1 O2 C7 -62.9(2) . . . . ? O10 Ba1 O2 C7 -32.86(19) 2_576 . . . ? O13 Ba1 O2 C7 162.8(6) . . . . ? O14A Ba1 O2 C7 -155.9(4) . . . . ? O17 Ba1 O5 C14 110.4(2) . . . . ? O2 Ba1 O5 C14 -167.7(2) . . . . ? O6 Ba1 O5 C14 -53.00(19) . . . . ? O1 Ba1 O5 C14 -114.1(2) . . . . ? O18 Ba1 O5 C14 -41.8(2) . . . . ? O13A Ba1 O5 C14 11.6(4) . . . . ? O9 Ba1 O5 C14 76.2(2) . . . . ? O10 Ba1 O5 C14 169.43(18) 2_576 . . . ? O13 Ba1 O5 C14 10.4(3) . . . . ? O14A Ba1 O5 C14 45.5(3) . . . . ? O17 Ba1 O6 C17 34.2(2) . . . . ? O2 Ba1 O6 C17 114.81(18) . . . . ? O5 Ba1 O6 C17 55.49(17) . . . . ? O1 Ba1 O6 C17 171.16(19) . . . . ? O18 Ba1 O6 C17 -117.43(18) . . . . ? O13A Ba1 O6 C17 -40.2(4) . . . . ? O9 Ba1 O6 C17 -70.6(2) . . . . ? O10 Ba1 O6 C17 172.37(16) 2_576 . . . ? O13 Ba1 O6 C17 -44.2(3) . . . . ? O14A Ba1 O6 C17 -8.9(3) . . . . ? O11 Cl1 O9 Ba1 -117.6(2) . . . . ? O12 Cl1 O9 Ba1 2.9(2) . . . . ? O10 Cl1 O9 Ba1 122.60(19) . . . . ? O17 Ba1 O9 Cl1 32.94(19) . . . . ? O2 Ba1 O9 Cl1 -24.1(2) . . . . ? O5 Ba1 O9 Cl1 67.7(2) . . . . ? O6 Ba1 O9 Cl1 162.20(17) . . . . ? O1 Ba1 O9 Cl1 -100.3(2) . . . . ? O18 Ba1 O9 Cl1 -148.1(2) . . . . ? O13A Ba1 O9 Cl1 134.4(4) . . . . ? O10 Ba1 O9 Cl1 -53.19(19) 2_576 . . . ? O13 Ba1 O9 Cl1 137.7(3) . . . . ? O14A Ba1 O9 Cl1 96.6(2) . . . . ? O9 Cl1 O10 Ba1 -125.28(12) . . . 2_576 ? O11 Cl1 O10 Ba1 114.78(14) . . . 2_576 ? O12 Cl1 O10 Ba1 -5.73(16) . . . 2_576 ? O15A Cl2 O13 Ba1 115.0(13) . . . . ? O16 Cl2 O13 Ba1 -111.4(10) . . . . ? O13A Cl2 O13 Ba1 -31(6) . . . . ? O14 Cl2 O13 Ba1 21.2(10) . . . . ? O15 Cl2 O13 Ba1 134.2(6) . . . . ? O14A Cl2 O13 Ba1 -9.5(10) . . . . ? O16A Cl2 O13 Ba1 -119.4(11) . . . . ? O17 Ba1 O13 Cl2 -9.5(8) . . . . ? O2 Ba1 O13 Cl2 66.0(11) . . . . ? O5 Ba1 O13 Cl2 61.8(7) . . . . ? O6 Ba1 O13 Cl2 122.6(8) . . . . ? O1 Ba1 O13 Cl2 164.3(6) . . . . ? O18 Ba1 O13 Cl2 -149.7(8) . . . . ? O13A Ba1 O13 Cl2 43(7) . . . . ? O9 Ba1 O13 Cl2 -75.8(7) . . . . ? O10 Ba1 O13 Cl2 -91.7(8) 2_576 . . . ? O14A Ba1 O13 Cl2 6.9(8) . . . . ? O15A Cl2 O13A Ba1 104.7(17) . . . . ? O16 Cl2 O13A Ba1 -114.7(11) . . . . ? O14 Cl2 O13A Ba1 9.8(12) . . . . ? O13 Cl2 O13A Ba1 141(7) . . . . ? O15 Cl2 O13A Ba1 126.2(9) . . . . ? O14A Cl2 O13A Ba1 -16.7(11) . . . . ? O16A Cl2 O13A Ba1 -124.4(13) . . . . ? O17 Ba1 O13A Cl2 -0.2(10) . . . . ? O2 Ba1 O13A Cl2 72.2(12) . . . . ? O5 Ba1 O13A Cl2 70.8(10) . . . . ? O6 Ba1 O13A Cl2 133.1(11) . . . . ? O1 Ba1 O13A Cl2 170.9(8) . . . . ? O18 Ba1 O13A Cl2 -140.6(10) . . . . ? O9 Ba1 O13A Cl2 -67.7(9) . . . . ? O10 Ba1 O13A Cl2 -79.4(12) 2_576 . . . ? O13 Ba1 O13A Cl2 -128(8) . . . . ? O14A Ba1 O13A Cl2 12.9(9) . . . . ? O15A Cl2 O14A Ba1 -110.6(9) . . . . ? O16 Cl2 O14A Ba1 122.9(9) . . . . ? O13A Cl2 O14A Ba1 11.6(8) . . . . ? O14 Cl2 O14A Ba1 -130.1(13) . . . . ? O13 Cl2 O14A Ba1 7.9(9) . . . . ? O15 Cl2 O14A Ba1 -97.9(10) . . . . ? O16A Cl2 O14A Ba1 113.6(12) . . . . ? O17 Ba1 O14A Cl2 155.3(11) . . . . ? O2 Ba1 O14A Cl2 -160.1(7) . . . . ? O5 Ba1 O14A Cl2 -122.1(10) . . . . ? O6 Ba1 O14A Cl2 -60.9(9) . . . . ? O1 Ba1 O14A Cl2 -60.7(14) . . . . ? O18 Ba1 O14A Cl2 17.2(10) . . . . ? O13A Ba1 O14A Cl2 -9.7(7) . . . . ? O9 Ba1 O14A Cl2 80.2(9) . . . . ? O10 Ba1 O14A Cl2 118.1(8) 2_576 . . . ? O13 Ba1 O14A Cl2 -6.0(7) . . . . ? C6 O3 C2 C3 -1.0(3) . . . . ? C6 O3 C2 C1 178.7(2) . . . . ? O3 C2 C3 C4 1.0(4) . . . . ? C1 C2 C3 C4 -178.7(3) . . . . ? Ba1 O1 C4 C3 -141.82(18) . . . . ? Ba1 O1 C4 C5 36.5(3) . . . . ? C2 C3 C4 O1 176.5(2) . . . . ? C2 C3 C4 C5 -1.9(3) . . . . ? O1 C4 C5 C6 -175.6(2) . . . . ? C3 C4 C5 C6 2.8(3) . . . . ? O1 C4 C5 C7 -0.4(3) . . . . ? C3 C4 C5 C7 178.0(2) . . . . ? C2 O3 C6 O4 -176.71(19) . . . . ? C2 O3 C6 C5 2.2(3) . . . . ? C9 O4 C6 O3 179.63(17) . . . . ? C9 O4 C6 C5 0.7(3) . . . . ? C4 C5 C6 O3 -3.2(3) . . . . ? C7 C5 C6 O3 -178.7(2) . . . . ? C4 C5 C6 O4 175.57(19) . . . . ? C7 C5 C6 O4 0.0(3) . . . . ? Ba1 O2 C7 C8 135.42(18) . . . . ? Ba1 O2 C7 C5 -45.1(3) . . . . ? C6 C5 C7 O2 179.9(2) . . . . ? C4 C5 C7 O2 4.7(3) . . . . ? C6 C5 C7 C8 -0.5(3) . . . . ? C4 C5 C7 C8 -175.7(2) . . . . ? O2 C7 C8 C9 179.9(2) . . . . ? C5 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 O4 0.3(3) . . . . ? C7 C8 C9 C10 -179.8(2) . . . . ? C6 O4 C9 C8 -0.9(3) . . . . ? C6 O4 C9 C10 179.3(2) . . . . ? C16 O7 C12 C13 -0.1(3) . . . . ? C16 O7 C12 C11 179.0(2) . . . . ? O7 C12 C13 C14 2.4(3) . . . . ? C11 C12 C13 C14 -176.5(2) . . . . ? Ba1 O5 C14 C13 -136.66(18) . . . . ? Ba1 O5 C14 C15 41.2(3) . . . . ? C12 C13 C14 O5 173.8(2) . . . . ? C12 C13 C14 C15 -4.2(3) . . . . ? O5 C14 C15 C16 -174.2(2) . . . . ? C13 C14 C15 C16 3.8(3) . . . . ? O5 C14 C15 C17 1.3(3) . . . . ? C13 C14 C15 C17 179.3(2) . . . . ? C12 O7 C16 O8 -178.35(17) . . . . ? C12 O7 C16 C15 -0.2(3) . . . . ? C19 O8 C16 O7 176.82(17) . . . . ? C19 O8 C16 C15 -1.4(3) . . . . ? C14 C15 C16 O7 -1.8(3) . . . . ? C17 C15 C16 O7 -177.67(19) . . . . ? C14 C15 C16 O8 176.06(19) . . . . ? C17 C15 C16 O8 0.2(3) . . . . ? Ba1 O6 C17 C18 130.18(18) . . . . ? Ba1 O6 C17 C15 -48.6(3) . . . . ? C16 C15 C17 O6 179.2(2) . . . . ? C14 C15 C17 O6 3.7(3) . . . . ? C16 C15 C17 C18 0.3(3) . . . . ? C14 C15 C17 C18 -175.2(2) . . . . ? O6 C17 C18 C19 -178.5(2) . . . . ? C15 C17 C18 C19 0.4(3) . . . . ? C17 C18 C19 O8 -1.6(4) . . . . ? C17 C18 C19 C20 176.6(2) . . . . ? C16 O8 C19 C18 2.1(3) . . . . ? C16 O8 C19 C20 -176.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O18 H1O O1 0.80(5) 2.22(5) 2.996(3) 163(4) 2_566 O18 H1O O18 0.80(5) 2.64(4) 3.080(4) 116(4) 2_566 O18 H2O O12 0.74(4) 2.41(4) 3.056(3) 146(4) 2_576 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.543 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.143 # Attachment '4-jw33.cif' data_jw33 _database_code_depnum_ccdc_archive 'CCDC 774942' #TrackingRef '4-jw33.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 O5' _chemical_formula_weight 210.18 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0711(2) _cell_length_b 25.5598(9) _cell_length_c 11.1908(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.5210(10) _cell_angle_gamma 90.00 _cell_volume 1957.97(11) _cell_formula_units_Z 8 _cell_measurement_temperature 173 _cell_measurement_reflns_used 3116 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 24.38 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19210 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4263 _reflns_number_gt 2740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0566P)^2^+0.1674P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4263 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.20170(19) 0.38373(4) 0.95856(11) 0.0561(4) Uani 1 1 d . . . O2 O 0.13044(18) 0.30667(4) 0.88548(10) 0.0497(3) Uani 1 1 d . . . O3 O -0.0230(2) 0.45887(5) 0.63622(13) 0.0720(4) Uani 1 1 d . . . O4 O -0.1466(2) 0.35615(5) 0.54196(12) 0.0657(4) Uani 1 1 d . . . C1 C 0.1160(2) 0.35740(6) 0.85733(16) 0.0443(4) Uani 1 1 d . . . C2 C 0.2047(3) 0.43785(7) 0.95345(17) 0.0558(5) Uani 1 1 d . . . C3 C 0.1266(3) 0.46250(8) 0.84864(18) 0.0569(5) Uani 1 1 d . . . C4 C 0.0379(3) 0.43563(7) 0.73443(17) 0.0517(5) Uani 1 1 d . . . C5 C 0.0318(2) 0.37840(6) 0.74538(15) 0.0433(4) Uani 1 1 d . . . C6 C -0.0567(3) 0.34221(7) 0.64587(16) 0.0467(4) Uani 1 1 d . . . C7 C -0.0337(3) 0.28723(7) 0.67961(17) 0.0485(4) Uani 1 1 d . . . C8 C 0.0521(2) 0.27109(6) 0.79308(16) 0.0442(4) Uani 1 1 d . . . C10 C 0.3066(5) 0.45951(10) 1.0752(2) 0.0754(7) Uani 1 1 d . . . C11 C 0.0768(4) 0.21683(7) 0.8406(2) 0.0549(5) Uani 1 1 d . . . O1' O 0.40799(18) 0.15437(5) 0.07997(11) 0.0554(3) Uani 1 1 d . . . O2' O 0.45220(18) 0.23373(5) 0.14792(11) 0.0528(3) Uani 1 1 d . . . O3' O 0.6550(3) 0.08802(5) 0.41069(14) 0.0826(5) Uani 1 1 d . . . O4' O 0.7424(2) 0.19159(5) 0.49400(12) 0.0709(4) Uani 1 1 d . . . C1' C 0.4803(2) 0.18344(7) 0.17982(16) 0.0452(4) Uani 1 1 d . . . C2' C 0.4229(3) 0.10041(7) 0.09105(18) 0.0543(5) Uani 1 1 d . . . C3' C 0.5041(3) 0.07849(8) 0.19923(19) 0.0581(5) Uani 1 1 d . . . C4' C 0.5828(3) 0.10841(7) 0.31070(18) 0.0544(5) Uani 1 1 d . . . C5' C 0.5676(2) 0.16511(7) 0.29388(16) 0.0451(4) Uani 1 1 d . . . C6' C 0.6451(3) 0.20342(7) 0.39075(17) 0.0486(4) Uani 1 1 d . . . C7' C 0.6013(3) 0.25720(8) 0.35380(18) 0.0507(5) Uani 1 1 d . . . C8' C 0.5130(3) 0.27119(7) 0.23968(17) 0.0497(4) Uani 1 1 d . . . C10' C 0.3396(5) 0.07493(12) -0.0297(3) 0.0784(7) Uani 1 1 d . . . C11' C 0.4652(5) 0.32474(9) 0.1918(3) 0.0685(6) Uani 1 1 d . . . O1S O 0.7905(3) 0.44326(9) 0.36362(17) 0.0857(6) Uani 1 1 d . . . O1S' O 0.9418(3) 0.10375(8) 0.6693(2) 0.0923(6) Uani 1 1 d . . . H1S H 0.818(5) 0.4270(12) 0.424(3) 0.127(13) Uiso 1 1 d . . . H1'S H 0.858(5) 0.1113(13) 0.609(3) 0.128(14) Uiso 1 1 d . . . H2S H 0.865(5) 0.4711(13) 0.375(3) 0.135(13) Uiso 1 1 d . . . H2'S H 0.885(5) 0.0947(14) 0.721(3) 0.145(17) Uiso 1 1 d . . . H3 H 0.132(3) 0.4993(8) 0.8500(16) 0.060(5) Uiso 1 1 d . . . H3' H 0.510(3) 0.0422(8) 0.2026(17) 0.065(6) Uiso 1 1 d . . . H7 H -0.087(3) 0.2611(7) 0.6193(18) 0.058(5) Uiso 1 1 d . . . H7' H 0.640(3) 0.2824(7) 0.4123(18) 0.058(6) Uiso 1 1 d . . . H10A H 0.442(4) 0.4472(10) 1.097(2) 0.111(10) Uiso 1 1 d . . . H10B H 0.241(4) 0.4485(10) 1.136(2) 0.103(9) Uiso 1 1 d . . . H10C H 0.301(3) 0.4975(11) 1.074(2) 0.102(8) Uiso 1 1 d . . . H10D H 0.213(5) 0.0908(12) -0.069(3) 0.143(13) Uiso 1 1 d . . . H10E H 0.420(4) 0.0790(10) -0.085(3) 0.113(10) Uiso 1 1 d . . . H10F H 0.332(4) 0.0397(10) -0.018(2) 0.098(9) Uiso 1 1 d . . . H11A H 0.207(3) 0.2095(8) 0.876(2) 0.077(7) Uiso 1 1 d . . . H11B H 0.004(3) 0.2112(8) 0.903(2) 0.087(7) Uiso 1 1 d . . . H11C H 0.031(3) 0.1911(8) 0.7706(18) 0.069(6) Uiso 1 1 d . . . H11D H 0.518(4) 0.3494(10) 0.258(2) 0.099(8) Uiso 1 1 d . . . H11E H 0.335(4) 0.3286(9) 0.165(2) 0.084(8) Uiso 1 1 d . . . H11F H 0.517(3) 0.3312(9) 0.121(2) 0.089(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0772(9) 0.0362(7) 0.0483(7) -0.0002(5) 0.0033(6) -0.0024(6) O2 0.0646(8) 0.0342(7) 0.0481(7) 0.0023(5) 0.0101(6) 0.0000(5) O3 0.0960(11) 0.0483(8) 0.0618(9) 0.0160(7) 0.0013(8) 0.0000(7) O4 0.0858(10) 0.0559(8) 0.0481(8) 0.0029(6) 0.0032(7) 0.0005(7) C1 0.0508(10) 0.0351(9) 0.0472(10) -0.0001(8) 0.0125(8) -0.0017(7) C2 0.0717(13) 0.0353(10) 0.0587(12) -0.0016(8) 0.0130(10) -0.0028(9) C3 0.0711(13) 0.0334(10) 0.0639(13) 0.0023(9) 0.0129(10) -0.0015(9) C4 0.0546(11) 0.0421(10) 0.0573(11) 0.0081(9) 0.0116(9) 0.0026(8) C5 0.0450(9) 0.0387(9) 0.0476(10) 0.0037(8) 0.0140(8) 0.0016(7) C6 0.0495(10) 0.0460(10) 0.0460(10) 0.0013(8) 0.0144(8) -0.0001(8) C7 0.0541(11) 0.0427(10) 0.0490(11) -0.0055(9) 0.0136(9) -0.0021(8) C8 0.0456(10) 0.0369(9) 0.0531(10) -0.0038(8) 0.0178(8) -0.0018(7) C10 0.110(2) 0.0471(14) 0.0608(14) -0.0084(11) 0.0061(14) -0.0093(13) C11 0.0602(13) 0.0371(11) 0.0682(13) 0.0045(10) 0.0180(11) 0.0019(9) O1' 0.0587(8) 0.0507(8) 0.0522(8) -0.0008(6) 0.0055(6) -0.0033(6) O2' 0.0607(8) 0.0434(7) 0.0503(7) 0.0065(6) 0.0066(6) 0.0011(6) O3' 0.1187(13) 0.0514(9) 0.0659(9) 0.0152(7) 0.0012(9) 0.0007(8) O4' 0.0896(11) 0.0584(9) 0.0525(8) 0.0049(7) -0.0049(7) 0.0033(7) C1' 0.0423(9) 0.0444(10) 0.0494(10) 0.0009(8) 0.0124(8) -0.0028(7) C2' 0.0535(11) 0.0483(11) 0.0626(12) -0.0023(9) 0.0171(9) -0.0048(9) C3' 0.0639(13) 0.0420(12) 0.0694(13) 0.0001(10) 0.0187(10) -0.0018(9) C4' 0.0586(12) 0.0452(11) 0.0591(12) 0.0079(9) 0.0142(9) -0.0008(9) C5' 0.0413(9) 0.0448(10) 0.0491(10) 0.0039(8) 0.0112(8) -0.0012(7) C6' 0.0473(10) 0.0497(11) 0.0496(10) 0.0057(8) 0.0136(8) 0.0025(8) C7' 0.0544(11) 0.0472(11) 0.0504(11) -0.0036(9) 0.0130(9) -0.0004(9) C8' 0.0535(11) 0.0442(10) 0.0531(11) 0.0005(8) 0.0166(9) -0.0007(8) C10' 0.096(2) 0.0650(17) 0.0716(16) -0.0149(13) 0.0149(15) -0.0143(15) C11' 0.090(2) 0.0490(13) 0.0672(15) 0.0108(11) 0.0216(14) 0.0078(12) O1S 0.1054(14) 0.0840(13) 0.0594(10) 0.0124(9) 0.0053(9) -0.0131(11) O1S' 0.1023(15) 0.0852(13) 0.0830(14) 0.0117(11) 0.0109(13) 0.0172(11) _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 1.326(2) . ? O1 C2 1.385(2) . ? O2 C1 1.3321(19) . ? O2 C8 1.384(2) . ? O3 C4 1.228(2) . ? O4 C6 1.230(2) . ? C1 C5 1.356(2) . ? C2 C3 1.324(3) . ? C2 C10 1.480(3) . ? C3 C4 1.448(3) . ? C3 H3 0.94(2) . ? C4 C5 1.469(2) . ? C5 C6 1.462(2) . ? C6 C7 1.454(2) . ? C7 C8 1.328(2) . ? C7 H7 0.958(19) . ? C8 C11 1.480(2) . ? C10 H10A 0.98(3) . ? C10 H10B 0.96(3) . ? C10 H10C 0.97(3) . ? C11 H11A 0.93(2) . ? C11 H11B 0.98(2) . ? C11 H11C 1.01(2) . ? O1' C1' 1.332(2) . ? O1' C2' 1.386(2) . ? O2' C1' 1.336(2) . ? O2' C8' 1.391(2) . ? O3' C4' 1.224(2) . ? O4' C6' 1.225(2) . ? C1' C5' 1.355(2) . ? C2' C3' 1.327(3) . ? C2' C10' 1.483(3) . ? C3' C4' 1.450(3) . ? C3' H3' 0.93(2) . ? C4' C5' 1.462(2) . ? C5' C6' 1.462(2) . ? C6' C7' 1.447(3) . ? C7' C8' 1.323(3) . ? C7' H7' 0.910(19) . ? C8' C11' 1.478(3) . ? C10' H10D 0.98(3) . ? C10' H10E 0.94(3) . ? C10' H10F 0.92(3) . ? C11' H11D 0.97(3) . ? C11' H11E 0.90(2) . ? C11' H11F 0.97(2) . ? O1S H1S 0.77(3) . ? O1S H2S 0.87(3) . ? O1S' H1'S 0.80(4) . ? O1S' H2'S 0.81(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 C1 O1 C2 118.69(14) . . ? C1 O2 C8 118.04(13) . . ? O1 C1 O2 107.48(14) . . ? O1 C1 C5 126.07(15) . . ? O2 C1 C5 126.44(16) . . ? C3 C2 O1 120.31(17) . . ? C3 C2 C10 129.52(19) . . ? O1 C2 C10 110.16(17) . . ? C2 C3 C4 123.25(18) . . ? C2 C3 H3 117.1(11) . . ? C4 C3 H3 119.7(11) . . ? O3 C4 C3 122.51(17) . . ? O3 C4 C5 123.03(17) . . ? C3 C4 C5 114.45(16) . . ? C1 C5 C6 117.26(15) . . ? C1 C5 C4 117.14(16) . . ? C6 C5 C4 125.60(15) . . ? O4 C6 C7 121.55(17) . . ? O4 C6 C5 123.92(16) . . ? C7 C6 C5 114.52(15) . . ? C8 C7 C6 122.90(17) . . ? C8 C7 H7 117.5(11) . . ? C6 C7 H7 119.5(11) . . ? C7 C8 O2 120.76(15) . . ? C7 C8 C11 128.23(17) . . ? O2 C8 C11 111.00(16) . . ? C2 C10 H10A 109.1(16) . . ? C2 C10 H10B 109.6(16) . . ? H10A C10 H10B 110(2) . . ? C2 C10 H10C 110.6(14) . . ? H10A C10 H10C 111(2) . . ? H10B C10 H10C 106(2) . . ? C8 C11 H11A 111.1(13) . . ? C8 C11 H11B 111.1(13) . . ? H11A C11 H11B 107.6(19) . . ? C8 C11 H11C 110.2(11) . . ? H11A C11 H11C 107.3(17) . . ? H11B C11 H11C 109.4(17) . . ? C1' O1' C2' 118.37(14) . . ? C1' O2' C8' 117.88(13) . . ? O1' C1' O2' 108.22(14) . . ? O1' C1' C5' 125.85(16) . . ? O2' C1' C5' 125.93(16) . . ? C3' C2' O1' 120.49(18) . . ? C3' C2' C10' 128.9(2) . . ? O1' C2' C10' 110.58(19) . . ? C2' C3' C4' 123.17(19) . . ? C2' C3' H3' 117.6(12) . . ? C4' C3' H3' 119.2(12) . . ? O3' C4' C3' 122.96(18) . . ? O3' C4' C5' 122.70(18) . . ? C3' C4' C5' 114.34(17) . . ? C1' C5' C6' 117.70(16) . . ? C1' C5' C4' 117.75(16) . . ? C6' C5' C4' 124.53(16) . . ? O4' C6' C7' 122.24(17) . . ? O4' C6' C5' 123.48(17) . . ? C7' C6' C5' 114.26(16) . . ? C8' C7' C6' 123.27(18) . . ? C8' C7' H7' 119.2(12) . . ? C6' C7' H7' 117.5(12) . . ? C7' C8' O2' 120.69(16) . . ? C7' C8' C11' 127.60(19) . . ? O2' C8' C11' 111.71(17) . . ? C2' C10' H10D 109.8(19) . . ? C2' C10' H10E 112.2(16) . . ? H10D C10' H10E 107(3) . . ? C2' C10' H10F 108.8(16) . . ? H10D C10' H10F 113(2) . . ? H10E C10' H10F 106(2) . . ? C8' C11' H11D 108.2(15) . . ? C8' C11' H11E 110.2(15) . . ? H11D C11' H11E 111(2) . . ? C8' C11' H11F 110.9(14) . . ? H11D C11' H11F 111(2) . . ? H11E C11' H11F 106(2) . . ? H1S O1S H2S 107(3) . . ? H1'S O1S' H2'S 106(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O1 C1 O2 -179.49(14) . . . . ? C2 O1 C1 C5 1.4(3) . . . . ? C8 O2 C1 O1 -179.43(13) . . . . ? C8 O2 C1 C5 -0.4(2) . . . . ? C1 O1 C2 C3 -1.3(3) . . . . ? C1 O1 C2 C10 -180.0(2) . . . . ? O1 C2 C3 C4 -1.1(3) . . . . ? C10 C2 C3 C4 177.3(3) . . . . ? C2 C3 C4 O3 -175.3(2) . . . . ? C2 C3 C4 C5 3.1(3) . . . . ? O1 C1 C5 C6 -179.36(16) . . . . ? O2 C1 C5 C6 1.7(3) . . . . ? O1 C1 C5 C4 0.8(3) . . . . ? O2 C1 C5 C4 -178.15(16) . . . . ? O3 C4 C5 C1 175.59(18) . . . . ? C3 C4 C5 C1 -2.9(2) . . . . ? O3 C4 C5 C6 -4.3(3) . . . . ? C3 C4 C5 C6 177.27(16) . . . . ? C1 C5 C6 O4 176.02(17) . . . . ? C4 C5 C6 O4 -4.1(3) . . . . ? C1 C5 C6 C7 -2.9(2) . . . . ? C4 C5 C6 C7 176.92(16) . . . . ? O4 C6 C7 C8 -175.75(18) . . . . ? C5 C6 C7 C8 3.2(2) . . . . ? C6 C7 C8 O2 -2.0(3) . . . . ? C6 C7 C8 C11 176.99(19) . . . . ? C1 O2 C8 C7 0.4(2) . . . . ? C1 O2 C8 C11 -178.73(16) . . . . ? C2' O1' C1' O2' 179.31(14) . . . . ? C2' O1' C1' C5' -0.5(3) . . . . ? C8' O2' C1' O1' 178.46(13) . . . . ? C8' O2' C1' C5' -1.7(2) . . . . ? C1' O1' C2' C3' 1.3(3) . . . . ? C1' O1' C2' C10' -178.50(19) . . . . ? O1' C2' C3' C4' -0.6(3) . . . . ? C10' C2' C3' C4' 179.1(2) . . . . ? C2' C3' C4' O3' 178.9(2) . . . . ? C2' C3' C4' C5' -0.7(3) . . . . ? O1' C1' C5' C6' 177.46(15) . . . . ? O2' C1' C5' C6' -2.4(3) . . . . ? O1' C1' C5' C4' -0.8(3) . . . . ? O2' C1' C5' C4' 179.37(16) . . . . ? O3' C4' C5' C1' -178.28(18) . . . . ? C3' C4' C5' C1' 1.4(2) . . . . ? O3' C4' C5' C6' 3.6(3) . . . . ? C3' C4' C5' C6' -176.78(16) . . . . ? C1' C5' C6' O4' -173.08(17) . . . . ? C4' C5' C6' O4' 5.1(3) . . . . ? C1' C5' C6' C7' 5.5(2) . . . . ? C4' C5' C6' C7' -176.31(16) . . . . ? O4' C6' C7' C8' 173.27(19) . . . . ? C5' C6' C7' C8' -5.4(3) . . . . ? C6' C7' C8' O2' 1.6(3) . . . . ? C6' C7' C8' C11' -178.6(2) . . . . ? C1' O2' C8' C7' 2.1(2) . . . . ? C1' O2' C8' C11' -177.66(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1S H1S O4 0.77(3) 2.22(3) 2.948(2) 157(3) 1_655 O1S H1S O3 0.77(3) 2.50(3) 3.031(2) 128(3) 1_655 O1S' H1'S O3' 0.80(4) 2.40(4) 3.116(3) 150(3) . O1S' H1'S O4' 0.80(4) 2.45(3) 3.081(3) 136(3) . O1S H2S O3 0.87(3) 2.13(3) 2.993(3) 168(3) 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.184 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.036 # Attachment '5-jw38a.cif' data_jw38a _database_code_depnum_ccdc_archive 'CCDC 774943' #TrackingRef '5-jw38a.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 Cl O8' _chemical_formula_weight 292.62 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.190(4) _cell_length_b 12.552(4) _cell_length_c 8.820(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1128.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3642 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.31 _exptl_crystal_description prizm _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8705 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Bruker Apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12297 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1291 _reflns_number_gt 1129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0568P)^2^+0.4566P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1291 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 Cl1 Cl 0.75472(5) 0.2500 0.03640(6) 0.02811(19) Uani 1 2 d S . . O1 O 0.49105(10) 0.66323(9) 0.24013(12) 0.0273(3) Uani 1 1 d . . . O2 O 0.80691(13) 0.64709(11) -0.03975(15) 0.0380(3) Uani 1 1 d . . . O3 O 0.8367(2) 0.2500 0.1667(2) 0.0530(6) Uani 1 2 d S . . O4 O 0.6200(2) 0.2500 0.0822(3) 0.0547(6) Uani 1 2 d S . . O5 O 0.77914(16) 0.34346(11) -0.05354(16) 0.0453(4) Uani 1 1 d . . . C1 C 0.5489(2) 0.7500 0.1898(2) 0.0267(5) Uani 1 2 d S . . C2 C 0.6554(2) 0.7500 0.0959(3) 0.0275(5) Uani 1 2 d S . . C3 C 0.70813(17) 0.65014(14) 0.04759(18) 0.0302(4) Uani 1 1 d . . . C4 C 0.64428(16) 0.55684(13) 0.10301(19) 0.0307(4) Uani 1 1 d . . . C5 C 0.53947(15) 0.56518(13) 0.19640(18) 0.0281(4) Uani 1 1 d . . . C6 C 0.4628(2) 0.47728(15) 0.2626(2) 0.0344(4) Uani 1 1 d . . . H1 H 0.828(4) 0.707(3) -0.060(4) 0.042(13) Uiso 0.50 1 d P . . H2 H 0.6730(19) 0.4861(16) 0.074(2) 0.034(5) Uiso 1 1 d . . . H3 H 0.502(2) 0.4151(19) 0.229(2) 0.043(6) Uiso 1 1 d . . . H4 H 0.464(2) 0.4836(18) 0.373(3) 0.052(6) Uiso 1 1 d . . . H5 H 0.372(3) 0.4844(17) 0.228(2) 0.051(6) Uiso 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 Cl1 0.0273(3) 0.0280(3) 0.0290(3) 0.000 0.0016(2) 0.000 O1 0.0234(6) 0.0267(6) 0.0317(6) 0.0007(4) 0.0004(4) -0.0008(4) O2 0.0341(7) 0.0386(8) 0.0413(8) -0.0017(6) 0.0096(5) 0.0031(6) O3 0.0609(13) 0.0510(12) 0.0471(12) 0.000 -0.0214(10) 0.000 O4 0.0348(11) 0.0686(14) 0.0605(13) 0.000 0.0168(10) 0.000 O5 0.0591(9) 0.0338(7) 0.0429(8) 0.0088(6) 0.0129(6) 0.0035(6) C1 0.0248(11) 0.0276(11) 0.0277(11) 0.000 -0.0058(9) 0.000 C2 0.0230(10) 0.0317(11) 0.0277(11) 0.000 -0.0030(9) 0.000 C3 0.0248(8) 0.0360(9) 0.0298(8) -0.0013(7) -0.0028(6) 0.0004(7) C4 0.0298(8) 0.0309(9) 0.0314(8) -0.0028(7) -0.0044(7) 0.0025(6) C5 0.0266(8) 0.0288(8) 0.0289(8) -0.0009(6) -0.0069(6) 0.0002(6) C6 0.0370(10) 0.0313(9) 0.0350(9) 0.0016(7) -0.0025(7) -0.0026(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 Cl1 O3 1.421(2) . ? Cl1 O4 1.431(2) . ? Cl1 O5 1.4378(14) 7_565 ? Cl1 O5 1.4378(14) . ? O1 C1 1.3157(17) . ? O1 C5 1.3810(19) . ? O2 C3 1.268(2) . ? O2 H1 0.81(4) . ? C1 O1 1.3157(17) 7_575 ? C1 C2 1.365(3) . ? C2 C3 1.429(2) 7_575 ? C2 C3 1.429(2) . ? C3 C4 1.426(2) . ? C4 C5 1.353(2) . ? C4 H2 0.97(2) . ? C5 C6 1.472(2) . ? C6 H3 0.92(2) . ? C6 H4 0.97(2) . ? C6 H5 0.98(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 O3 Cl1 O4 109.63(14) . . ? O3 Cl1 O5 110.15(8) . 7_565 ? O4 Cl1 O5 108.77(8) . 7_565 ? O3 Cl1 O5 110.15(8) . . ? O4 Cl1 O5 108.77(8) . . ? O5 Cl1 O5 109.34(12) 7_565 . ? C1 O1 C5 118.91(13) . . ? C3 O2 H1 109(3) . . ? O1 C1 O1 111.74(19) . 7_575 ? O1 C1 C2 124.13(10) . . ? O1 C1 C2 124.13(10) 7_575 . ? C1 C2 C3 118.67(11) . 7_575 ? C1 C2 C3 118.67(11) . . ? C3 C2 C3 122.6(2) 7_575 . ? O2 C3 C4 123.07(16) . . ? O2 C3 C2 120.40(16) . . ? C4 C3 C2 116.53(16) . . ? C5 C4 C3 120.36(16) . . ? C5 C4 H2 118.2(11) . . ? C3 C4 H2 121.5(12) . . ? C4 C5 O1 121.40(14) . . ? C4 C5 C6 127.03(16) . . ? O1 C5 C6 111.57(14) . . ? C5 C6 H3 106.1(14) . . ? C5 C6 H4 109.0(14) . . ? H3 C6 H4 112.2(18) . . ? C5 C6 H5 108.0(13) . . ? H3 C6 H5 112.7(18) . . ? H4 C6 H5 108.7(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C1 O1 179.45(11) . . . 7_575 ? C5 O1 C1 C2 -0.1(3) . . . . ? O1 C1 C2 C3 179.15(18) . . . 7_575 ? O1 C1 C2 C3 -0.3(3) 7_575 . . 7_575 ? O1 C1 C2 C3 0.3(3) . . . . ? O1 C1 C2 C3 -179.15(18) 7_575 . . . ? C1 C2 C3 O2 179.93(18) . . . . ? C3 C2 C3 O2 1.2(3) 7_575 . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C3 C2 C3 C4 -179.03(14) 7_575 . . . ? O2 C3 C4 C5 179.77(16) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 O1 0.3(2) . . . . ? C3 C4 C5 C6 179.78(16) . . . . ? C1 O1 C5 C4 -0.2(2) . . . . ? C1 O1 C5 C6 -179.80(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1 O2 0.81(4) 1.85(4) 2.583(3) 151(4) 7_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.473 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.060 # Attachment '7a-jw45a.cif' data_jw45a _database_code_depnum_ccdc_archive 'CCDC 774944' #TrackingRef '7a-jw45a.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cl2 Mg O19' _chemical_formula_weight 689.64 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' Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.050(3) _cell_length_b 18.021(3) _cell_length_c 11.008(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.023(3) _cell_angle_gamma 90.00 _cell_volume 2908.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5288 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9277 _exptl_absorpt_correction_T_max 0.9613 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27023 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5118 _reflns_number_gt 3836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0832P)^2^+3.3721P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5118 _refine_ls_number_parameters 500 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.174 _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 Mg1 Mg 0.5000 0.5000 0.5000 0.0239(4) Uani 1 2 d S . . O1 O 0.55900(17) 0.60141(13) 0.5558(2) 0.0261(6) Uani 1 1 d . . . O2 O 0.45951(18) 0.49992(14) 0.6673(2) 0.0302(6) Uani 1 1 d . . . O3 O 0.54379(17) 0.73619(13) 0.8464(2) 0.0257(6) Uani 1 1 d . . . O4 O 0.46577(16) 0.65886(13) 0.9302(2) 0.0241(6) Uani 1 1 d . . . O5 O 0.38335(19) 0.55633(16) 0.4205(3) 0.0403(7) Uani 1 1 d D . . C1 C 0.6373(4) 0.8300(2) 0.7952(4) 0.0357(10) Uani 1 1 d . . . C2 C 0.5927(3) 0.7575(2) 0.7599(3) 0.0264(8) Uani 1 1 d . . . C3 C 0.5967(3) 0.71367(19) 0.6624(3) 0.0249(8) Uani 1 1 d . . . C4 C 0.5536(2) 0.64240(19) 0.6452(3) 0.0220(7) Uani 1 1 d . . . C5 C 0.5055(2) 0.62056(18) 0.7407(3) 0.0211(7) Uani 1 1 d . . . C6 C 0.5050(2) 0.66982(19) 0.8345(3) 0.0209(7) Uani 1 1 d . . . C7 C 0.4623(2) 0.54913(19) 0.7470(3) 0.0225(8) Uani 1 1 d . . . C8 C 0.4226(2) 0.5383(2) 0.8534(3) 0.0249(8) Uani 1 1 d . . . C9 C 0.4243(2) 0.59165(19) 0.9391(3) 0.0232(8) Uani 1 1 d . . . C10 C 0.3851(3) 0.5894(3) 1.0506(4) 0.0325(9) Uani 1 1 d . . . C11 C 0.3025(3) 0.5319(3) 0.3386(5) 0.0559(13) Uani 1 1 d . . . H11A H 0.2599 0.5735 0.3182 0.084 Uiso 1 1 calc R . . H11B H 0.2747 0.4925 0.3787 0.084 Uiso 1 1 calc R . . H11C H 0.3170 0.5128 0.2620 0.084 Uiso 1 1 calc R . . Mg1' Mg 0.0000 1.0000 1.0000 0.0232(4) Uani 1 2 d S . . O1' O 0.05027(17) 0.99919(13) 0.8410(2) 0.0287(6) Uani 1 1 d . . . O2' O -0.04798(17) 0.89557(13) 0.9526(2) 0.0271(6) Uani 1 1 d . . . O3' O 0.02438(16) 0.84836(13) 0.5609(2) 0.0256(6) Uani 1 1 d . . . O4' O -0.05231(16) 0.77037(13) 0.6446(2) 0.0244(6) Uani 1 1 d . . . O5' O 0.12079(19) 0.95386(17) 1.0982(3) 0.0426(7) Uani 1 1 d D . . C1' C 0.1095(3) 0.9161(3) 0.4442(4) 0.0334(9) Uani 1 1 d . . . C2' C 0.0730(2) 0.91308(19) 0.5581(3) 0.0242(8) Uani 1 1 d . . . C3' C 0.0817(2) 0.9629(2) 0.6503(3) 0.0252(8) Uani 1 1 d . . . C4' C 0.0431(2) 0.95133(19) 0.7572(3) 0.0220(8) Uani 1 1 d . . . C5' C -0.0033(2) 0.88133(18) 0.7600(3) 0.0204(7) Uani 1 1 d . . . C6' C -0.0101(2) 0.83505(19) 0.6599(3) 0.0210(7) Uani 1 1 d . . . C7' C -0.0473(2) 0.85707(19) 0.8583(3) 0.0219(7) Uani 1 1 d . . . C8' C -0.0917(3) 0.78630(19) 0.8389(3) 0.0256(8) Uani 1 1 d . . . C9' C -0.0943(2) 0.74582(19) 0.7362(3) 0.0239(8) Uani 1 1 d . . . C10' C -0.1401(3) 0.6737(2) 0.7007(4) 0.0343(10) Uani 1 1 d . . . C11' C 0.2069(3) 0.9867(3) 1.1392(6) 0.0701(16) Uani 1 1 d . . . H11D H 0.2499 0.9498 1.1839 0.105 Uiso 1 1 calc R . . H11E H 0.2023 1.0281 1.1952 0.105 Uiso 1 1 calc R . . H11F H 0.2285 1.0051 1.0672 0.105 Uiso 1 1 calc R . . Cl1 Cl 0.21107(8) 0.76683(6) 0.21055(10) 0.0438(3) Uani 1 1 d D . . O6 O 0.2867(3) 0.7999(3) 0.2822(5) 0.1075(18) Uani 1 1 d D A . O7 O 0.1389(7) 0.7713(8) 0.2684(12) 0.164(5) Uani 0.638(4) 1 d PD A 1 O8 O 0.1875(6) 0.8070(4) 0.0967(6) 0.094(2) Uani 0.638(4) 1 d PD A 1 O9 O 0.2227(5) 0.6935(3) 0.1810(8) 0.0786(19) Uani 0.638(4) 1 d PD A 1 O7A O 0.2298(12) 0.7327(15) 0.109(2) 0.164(5) Uani 0.362(4) 1 d PD A 2 O8A O 0.1831(11) 0.7048(8) 0.2736(13) 0.094(2) Uani 0.362(4) 1 d PD A 2 O9A O 0.1324(8) 0.8090(6) 0.1720(16) 0.0786(19) Uani 0.362(4) 1 d PD A 2 Cl2 Cl 0.25730(6) 0.12080(5) 0.50211(8) 0.0310(3) Uani 1 1 d D . . O10 O 0.2518(2) 0.19909(17) 0.5146(3) 0.0583(10) Uani 1 1 d D B . O11 O 0.3491(2) 0.1062(2) 0.4874(4) 0.0449(10) Uani 0.804(4) 1 d PD B 1 O12 O 0.1966(3) 0.0964(2) 0.3975(5) 0.0735(16) Uani 0.804(4) 1 d PD B 1 O13 O 0.2499(4) 0.0829(2) 0.6119(4) 0.0713(16) Uani 0.804(4) 1 d PD B 1 O11A O 0.1681(9) 0.1052(9) 0.5217(15) 0.0449(10) Uani 0.196(4) 1 d PD B 2 O12A O 0.3162(14) 0.0898(10) 0.578(2) 0.0735(16) Uani 0.196(4) 1 d PD B 2 O13A O 0.2492(18) 0.0841(11) 0.3934(16) 0.0713(3) Uani 0.196(4) 1 d PD B 2 O1S O 0.3596(2) 0.69366(19) 0.4949(3) 0.0574(9) Uani 1 1 d D . . H1A H 0.593(3) 0.864(3) 0.802(4) 0.056(15) Uiso 1 1 d . . . H1B H 0.671(3) 0.847(3) 0.748(5) 0.054(15) Uiso 1 1 d . . . H1C H 0.682(3) 0.825(2) 0.878(4) 0.045(13) Uiso 1 1 d . . . H1'A H 0.055(3) 0.907(3) 0.365(5) 0.061(14) Uiso 1 1 d . . . H1'B H 0.154(3) 0.877(3) 0.447(4) 0.049(13) Uiso 1 1 d . . . H1'C H 0.138(3) 0.960(3) 0.445(4) 0.045(13) Uiso 1 1 d . . . H3 H 0.626(2) 0.7315(19) 0.604(3) 0.020(9) Uiso 1 1 d . . . H3' H 0.116(3) 1.007(2) 0.643(3) 0.026(10) Uiso 1 1 d . . . H5'O H 0.124(3) 0.9024(12) 1.105(4) 0.058(15) Uiso 1 1 d D . . H5O H 0.383(4) 0.6072(15) 0.441(6) 0.10(2) Uiso 1 1 d D . . H8 H 0.395(3) 0.490(2) 0.865(4) 0.034(11) Uiso 1 1 d . . . H8' H -0.121(2) 0.766(2) 0.898(3) 0.025(9) Uiso 1 1 d . . . H10A H 0.435(3) 0.598(2) 1.128(4) 0.048(13) Uiso 1 1 d . . . H10B H 0.341(3) 0.628(3) 1.047(4) 0.050(13) Uiso 1 1 d . . . H10C H 0.361(3) 0.542(3) 1.053(4) 0.048(13) Uiso 1 1 d . . . H10D H -0.101(3) 0.641(3) 0.689(4) 0.042(13) Uiso 1 1 d . . . H10E H -0.170(3) 0.654(3) 0.763(4) 0.048(13) Uiso 1 1 d . . . H10F H -0.188(3) 0.682(2) 0.623(4) 0.041(12) Uiso 1 1 d . . . H1S H 0.317(5) 0.697(5) 0.552(7) 0.20(4) Uiso 1 1 d D . . H2S H 0.340(5) 0.721(4) 0.416(4) 0.13(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mg1 0.0309(9) 0.0227(9) 0.0191(8) -0.0047(7) 0.0078(7) -0.0012(7) O1 0.0365(14) 0.0242(13) 0.0200(13) -0.0051(10) 0.0119(11) -0.0041(11) O2 0.0439(16) 0.0239(13) 0.0256(14) -0.0057(11) 0.0140(12) -0.0090(11) O3 0.0364(14) 0.0200(13) 0.0243(13) -0.0042(10) 0.0148(11) -0.0018(11) O4 0.0295(13) 0.0254(13) 0.0205(13) -0.0040(10) 0.0121(10) -0.0027(11) O5 0.0346(16) 0.0363(17) 0.0448(17) -0.0045(14) -0.0024(13) 0.0047(13) C1 0.054(3) 0.023(2) 0.036(3) -0.0037(18) 0.021(2) -0.010(2) C2 0.037(2) 0.0219(19) 0.0234(19) 0.0048(15) 0.0127(16) -0.0003(16) C3 0.033(2) 0.0243(19) 0.0189(18) 0.0018(15) 0.0086(15) -0.0006(16) C4 0.0251(18) 0.0216(18) 0.0195(18) 0.0007(14) 0.0052(14) 0.0014(14) C5 0.0240(17) 0.0219(18) 0.0180(17) 0.0002(14) 0.0061(14) 0.0010(14) C6 0.0217(17) 0.0217(18) 0.0195(17) -0.0001(14) 0.0053(14) 0.0001(14) C7 0.0278(19) 0.0200(18) 0.0198(18) -0.0006(14) 0.0055(14) 0.0000(14) C8 0.0275(19) 0.0234(19) 0.0248(19) 0.0030(15) 0.0081(15) -0.0012(15) C9 0.0233(18) 0.0257(19) 0.0213(18) 0.0029(15) 0.0065(14) 0.0020(15) C10 0.039(2) 0.033(2) 0.031(2) -0.0025(18) 0.0200(19) -0.004(2) C11 0.048(3) 0.058(3) 0.053(3) 0.000(2) -0.006(2) 0.000(2) Mg1' 0.0308(9) 0.0220(9) 0.0181(8) -0.0033(7) 0.0081(7) 0.0005(7) O1' 0.0400(15) 0.0238(13) 0.0249(14) -0.0054(11) 0.0127(11) -0.0083(11) O2' 0.0407(15) 0.0255(13) 0.0180(13) -0.0045(10) 0.0126(11) -0.0031(11) O3' 0.0319(14) 0.0282(13) 0.0202(13) -0.0046(10) 0.0132(11) -0.0051(11) O4' 0.0316(13) 0.0220(13) 0.0219(13) -0.0033(10) 0.0112(10) -0.0033(11) O5' 0.0338(16) 0.0405(18) 0.0485(18) 0.0066(14) -0.0014(13) 0.0032(14) C1' 0.040(2) 0.034(2) 0.031(2) -0.0029(18) 0.0187(19) -0.004(2) C2' 0.0266(18) 0.0257(19) 0.0226(19) 0.0021(15) 0.0103(15) -0.0019(15) C3' 0.0281(19) 0.0241(19) 0.0246(19) 0.0026(15) 0.0086(15) -0.0013(16) C4' 0.0234(18) 0.0226(19) 0.0196(18) 0.0022(14) 0.0041(14) 0.0037(14) C5' 0.0227(17) 0.0214(18) 0.0172(17) -0.0002(14) 0.0045(13) 0.0024(14) C6' 0.0211(17) 0.0228(19) 0.0205(18) 0.0020(14) 0.0078(14) 0.0013(14) C7' 0.0246(18) 0.0222(18) 0.0186(18) 0.0016(14) 0.0044(14) 0.0027(14) C8' 0.034(2) 0.0229(19) 0.0228(19) 0.0027(15) 0.0123(16) -0.0012(16) C9' 0.0293(19) 0.0205(18) 0.0239(18) 0.0046(14) 0.0101(15) 0.0012(15) C10' 0.048(3) 0.025(2) 0.034(2) -0.0027(18) 0.018(2) -0.005(2) C11' 0.039(3) 0.072(4) 0.090(4) -0.011(3) -0.004(3) 0.006(3) Cl1 0.0470(6) 0.0365(6) 0.0468(6) -0.0018(5) 0.0080(5) 0.0012(5) O6 0.076(3) 0.084(3) 0.139(4) 0.003(3) -0.026(3) -0.038(3) O7 0.119(7) 0.231(12) 0.176(9) -0.150(9) 0.108(7) -0.084(8) O8 0.126(6) 0.082(5) 0.067(4) 0.024(3) 0.008(4) 0.016(4) O9 0.073(4) 0.038(3) 0.117(6) -0.008(3) 0.005(4) 0.011(3) O7A 0.119(7) 0.231(12) 0.176(9) -0.150(9) 0.108(7) -0.084(8) O8A 0.126(6) 0.082(5) 0.067(4) 0.024(3) 0.008(4) 0.016(4) O9A 0.073(4) 0.038(3) 0.117(6) -0.008(3) 0.005(4) 0.011(3) Cl2 0.0370(5) 0.0246(5) 0.0345(5) 0.0011(4) 0.0145(4) 0.0021(4) O10 0.052(2) 0.0244(17) 0.096(3) 0.0003(16) 0.0109(19) 0.0028(14) O11 0.0327(19) 0.056(2) 0.050(2) -0.0076(18) 0.0171(17) 0.0083(17) O12 0.055(3) 0.049(3) 0.091(4) -0.010(2) -0.035(3) 0.002(2) O13 0.116(4) 0.053(3) 0.066(3) 0.018(2) 0.064(3) 0.009(3) O11A 0.0327(19) 0.056(2) 0.050(2) -0.0076(18) 0.0171(17) 0.0083(17) O12A 0.055(3) 0.049(3) 0.091(4) -0.010(2) -0.035(3) 0.002(2) O13A 0.1160(2) 0.05287(19) 0.0654(3) 0.016(2) 0.0634(19) 0.009(2) O1S 0.063(2) 0.0434(19) 0.063(2) -0.0016(17) 0.0092(19) 0.0130(17) _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 Mg1 O5 2.046(3) 3_666 ? Mg1 O5 2.046(3) . ? Mg1 O1 2.064(2) 3_666 ? Mg1 O1 2.064(2) . ? Mg1 O2 2.066(2) 3_666 ? Mg1 O2 2.066(2) . ? Mg1 H5O 2.60(5) . ? O1 C4 1.248(4) . ? O2 C7 1.241(4) . ? O3 C6 1.324(4) . ? O3 C2 1.383(4) . ? O4 C6 1.332(4) . ? O4 C9 1.376(4) . ? O5 C11 1.411(5) . ? O5 H5O 0.95(2) . ? C1 C2 1.479(5) . ? C1 H1A 0.92(5) . ? C1 H1B 0.85(5) . ? C1 H1C 1.01(5) . ? C2 C3 1.345(5) . ? C3 C4 1.432(5) . ? C3 H3 0.92(4) . ? C4 C5 1.459(5) . ? C5 C6 1.363(5) . ? C5 C7 1.450(5) . ? C7 C8 1.443(5) . ? C8 C9 1.344(5) . ? C8 H8 0.99(4) . ? C9 C10 1.477(5) . ? C10 H10A 1.01(5) . ? C10 H10B 0.96(5) . ? C10 H10C 0.93(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? Mg1' O2' 2.041(2) . ? Mg1' O2' 2.041(2) 3_577 ? Mg1' O1' 2.057(2) 3_577 ? Mg1' O1' 2.057(2) . ? Mg1' O5' 2.068(3) . ? Mg1' O5' 2.068(3) 3_577 ? O1' C4' 1.250(4) . ? O2' C7' 1.250(4) . ? O3' C6' 1.330(4) . ? O3' C2' 1.381(4) . ? O4' C6' 1.320(4) . ? O4' C9' 1.378(4) . ? O5' C11' 1.403(6) . ? O5' H5'O 0.93(2) . ? C1' C2' 1.478(5) . ? C1' H1'A 1.06(5) . ? C1' H1'B 0.97(5) . ? C1' H1'C 0.90(5) . ? C2' C3' 1.340(5) . ? C3' C4' 1.440(5) . ? C3' H3' 0.96(4) . ? C4' C5' 1.445(5) . ? C5' C6' 1.367(5) . ? C5' C7' 1.458(5) . ? C7' C8' 1.433(5) . ? C8' C9' 1.339(5) . ? C8' H8' 0.94(4) . ? C9' C10' 1.481(5) . ? C10' H10D 0.86(5) . ? C10' H10E 0.97(5) . ? C10' H10F 1.00(5) . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? Cl1 O7A 1.362(11) . ? Cl1 O6 1.367(4) . ? Cl1 O7 1.379(7) . ? Cl1 O9 1.382(6) . ? Cl1 O9A 1.391(10) . ? Cl1 O8 1.422(6) . ? Cl1 O8A 1.428(11) . ? Cl2 O12A 1.211(14) . ? Cl2 O12 1.371(4) . ? Cl2 O13 1.414(4) . ? Cl2 O10 1.422(3) . ? Cl2 O11 1.451(3) . ? Cl2 O13A 1.349(16) . ? Cl2 O11A 1.435(12) . ? O1S H1S 1.00(2) . ? O1S H2S 0.98(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 O5 Mg1 O5 180.0 3_666 . ? O5 Mg1 O1 87.60(11) 3_666 3_666 ? O5 Mg1 O1 92.40(11) . 3_666 ? O5 Mg1 O1 92.40(11) 3_666 . ? O5 Mg1 O1 87.60(11) . . ? O1 Mg1 O1 180.000(1) 3_666 . ? O5 Mg1 O2 89.12(11) 3_666 3_666 ? O5 Mg1 O2 90.88(11) . 3_666 ? O1 Mg1 O2 85.92(9) 3_666 3_666 ? O1 Mg1 O2 94.08(9) . 3_666 ? O5 Mg1 O2 90.89(11) 3_666 . ? O5 Mg1 O2 89.11(11) . . ? O1 Mg1 O2 94.08(9) 3_666 . ? O1 Mg1 O2 85.92(9) . . ? O2 Mg1 O2 180.000(1) 3_666 . ? O5 Mg1 H5O 160.8(11) 3_666 . ? O5 Mg1 H5O 19.2(10) . . ? O1 Mg1 H5O 111.3(11) 3_666 . ? O1 Mg1 H5O 68.7(10) . . ? O2 Mg1 H5O 95.5(13) 3_666 . ? O2 Mg1 H5O 84.5(13) . . ? C4 O1 Mg1 131.2(2) . . ? C7 O2 Mg1 131.3(2) . . ? C6 O3 C2 118.3(3) . . ? C6 O4 C9 118.4(3) . . ? C11 O5 Mg1 130.6(3) . . ? C11 O5 H5O 114(4) . . ? Mg1 O5 H5O 115(4) . . ? C2 C1 H1A 109(3) . . ? C2 C1 H1B 116(3) . . ? H1A C1 H1B 110(4) . . ? C2 C1 H1C 109(3) . . ? H1A C1 H1C 109(4) . . ? H1B C1 H1C 102(4) . . ? C3 C2 O3 120.8(3) . . ? C3 C2 C1 129.0(3) . . ? O3 C2 C1 110.2(3) . . ? C2 C3 C4 122.2(3) . . ? C2 C3 H3 118(2) . . ? C4 C3 H3 120(2) . . ? O1 C4 C3 121.8(3) . . ? O1 C4 C5 122.7(3) . . ? C3 C4 C5 115.5(3) . . ? C6 C5 C7 117.6(3) . . ? C6 C5 C4 117.3(3) . . ? C7 C5 C4 125.0(3) . . ? O3 C6 O4 108.7(3) . . ? O3 C6 C5 125.8(3) . . ? O4 C6 C5 125.5(3) . . ? O2 C7 C8 121.5(3) . . ? O2 C7 C5 123.0(3) . . ? C8 C7 C5 115.5(3) . . ? C9 C8 C7 121.9(3) . . ? C9 C8 H8 119(2) . . ? C7 C8 H8 119(2) . . ? C8 C9 O4 121.1(3) . . ? C8 C9 C10 128.1(3) . . ? O4 C9 C10 110.8(3) . . ? C9 C10 H10A 110(3) . . ? C9 C10 H10B 111(3) . . ? H10A C10 H10B 107(4) . . ? C9 C10 H10C 106(3) . . ? H10A C10 H10C 110(4) . . ? H10B C10 H10C 113(4) . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2' Mg1' O2' 180.000(1) . 3_577 ? O2' Mg1' O1' 92.72(9) . 3_577 ? O2' Mg1' O1' 87.28(9) 3_577 3_577 ? O2' Mg1' O1' 87.28(9) . . ? O2' Mg1' O1' 92.72(9) 3_577 . ? O1' Mg1' O1' 180.000(1) 3_577 . ? O2' Mg1' O5' 88.95(11) . . ? O2' Mg1' O5' 91.05(11) 3_577 . ? O1' Mg1' O5' 90.38(11) 3_577 . ? O1' Mg1' O5' 89.62(12) . . ? O2' Mg1' O5' 91.05(11) . 3_577 ? O2' Mg1' O5' 88.95(11) 3_577 3_577 ? O1' Mg1' O5' 89.62(12) 3_577 3_577 ? O1' Mg1' O5' 90.38(12) . 3_577 ? O5' Mg1' O5' 180.000(1) . 3_577 ? C4' O1' Mg1' 130.2(2) . . ? C7' O2' Mg1' 131.0(2) . . ? C6' O3' C2' 118.5(3) . . ? C6' O4' C9' 118.5(3) . . ? C11' O5' Mg1' 129.6(3) . . ? C11' O5' H5'O 112(3) . . ? Mg1' O5' H5'O 118(3) . . ? C2' C1' H1'A 109(3) . . ? C2' C1' H1'B 110(3) . . ? H1'A C1' H1'B 108(4) . . ? C2' C1' H1'C 107(3) . . ? H1'A C1' H1'C 115(4) . . ? H1'B C1' H1'C 108(4) . . ? C3' C2' O3' 120.7(3) . . ? C3' C2' C1' 128.8(3) . . ? O3' C2' C1' 110.5(3) . . ? C2' C3' C4' 122.2(3) . . ? C2' C3' H3' 117(2) . . ? C4' C3' H3' 120(2) . . ? O1' C4' C3' 121.3(3) . . ? O1' C4' C5' 123.3(3) . . ? C3' C4' C5' 115.4(3) . . ? C6' C5' C4' 117.7(3) . . ? C6' C5' C7' 116.8(3) . . ? C4' C5' C7' 125.4(3) . . ? O4' C6' O3' 108.6(3) . . ? O4' C6' C5' 126.1(3) . . ? O3' C6' C5' 125.3(3) . . ? O2' C7' C8' 121.8(3) . . ? O2' C7' C5' 122.7(3) . . ? C8' C7' C5' 115.5(3) . . ? C9' C8' C7' 122.3(3) . . ? C9' C8' H8' 116(2) . . ? C7' C8' H8' 121(2) . . ? C8' C9' O4' 120.8(3) . . ? C8' C9' C10' 128.6(3) . . ? O4' C9' C10' 110.6(3) . . ? C9' C10' H10D 110(3) . . ? C9' C10' H10E 113(3) . . ? H10D C10' H10E 107(4) . . ? C9' C10' H10F 107(2) . . ? H10D C10' H10F 112(4) . . ? H10E C10' H10F 108(4) . . ? O5' C11' H11D 109.5 . . ? O5' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? O5' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? O7A Cl1 O6 111.8(7) . . ? O7A Cl1 O7 137.4(7) . . ? O6 Cl1 O7 110.4(4) . . ? O7A Cl1 O9 46.7(11) . . ? O6 Cl1 O9 114.8(4) . . ? O7 Cl1 O9 108.6(6) . . ? O7A Cl1 O9A 108.4(13) . . ? O6 Cl1 O9A 118.6(5) . . ? O7 Cl1 O9A 53.4(7) . . ? O9 Cl1 O9A 126.6(5) . . ? O7A Cl1 O8 64.0(13) . . ? O6 Cl1 O8 107.3(4) . . ? O7 Cl1 O8 108.1(7) . . ? O9 Cl1 O8 107.4(4) . . ? O9A Cl1 O8 55.0(7) . . ? O7A Cl1 O8A 100.7(12) . . ? O6 Cl1 O8A 111.1(6) . . ? O7 Cl1 O8A 58.1(7) . . ? O9 Cl1 O8A 55.4(7) . . ? O9A Cl1 O8A 104.6(8) . . ? O8 Cl1 O8A 141.7(6) . . ? O12A Cl2 O12 132.8(9) . . ? O12A Cl2 O13 51.1(13) . . ? O12 Cl2 O13 113.4(3) . . ? O12A Cl2 O10 116.1(9) . . ? O12 Cl2 O10 110.9(2) . . ? O13 Cl2 O10 112.3(2) . . ? O12A Cl2 O11 55.0(13) . . ? O12 Cl2 O11 108.6(3) . . ? O13 Cl2 O11 105.5(3) . . ? O10 Cl2 O11 105.6(2) . . ? O12A Cl2 O13A 107.1(15) . . ? O12 Cl2 O13A 35.6(10) . . ? O13 Cl2 O13A 120.9(9) . . ? O10 Cl2 O13A 125.2(9) . . ? O11 Cl2 O13A 73.1(11) . . ? O12A Cl2 O11A 111.7(15) . . ? O12 Cl2 O11A 66.1(7) . . ? O13 Cl2 O11A 61.4(7) . . ? O10 Cl2 O11A 95.9(6) . . ? O11 Cl2 O11A 158.2(7) . . ? O13A Cl2 O11A 97.9(12) . . ? H1S O1S H2S 115(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Mg1 O1 C4 -100.0(3) 3_666 . . . ? O5 Mg1 O1 C4 80.0(3) . . . . ? O1 Mg1 O1 C4 94(100) 3_666 . . . ? O2 Mg1 O1 C4 170.7(3) 3_666 . . . ? O2 Mg1 O1 C4 -9.3(3) . . . . ? O5 Mg1 O2 C7 101.7(3) 3_666 . . . ? O5 Mg1 O2 C7 -78.3(3) . . . . ? O1 Mg1 O2 C7 -170.6(3) 3_666 . . . ? O1 Mg1 O2 C7 9.4(3) . . . . ? O2 Mg1 O2 C7 -56(100) 3_666 . . . ? O5 Mg1 O5 C11 112(100) 3_666 . . . ? O1 Mg1 O5 C11 -10.8(4) 3_666 . . . ? O1 Mg1 O5 C11 169.2(4) . . . . ? O2 Mg1 O5 C11 75.2(4) 3_666 . . . ? O2 Mg1 O5 C11 -104.8(4) . . . . ? C6 O3 C2 C3 3.6(5) . . . . ? C6 O3 C2 C1 -175.0(3) . . . . ? O3 C2 C3 C4 -2.1(6) . . . . ? C1 C2 C3 C4 176.2(4) . . . . ? Mg1 O1 C4 C3 -176.1(2) . . . . ? Mg1 O1 C4 C5 5.5(5) . . . . ? C2 C3 C4 O1 -178.6(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? O1 C4 C5 C6 179.4(3) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? O1 C4 C5 C7 2.8(5) . . . . ? C3 C4 C5 C7 -175.6(3) . . . . ? C2 O3 C6 O4 176.7(3) . . . . ? C2 O3 C6 C5 -2.9(5) . . . . ? C9 O4 C6 O3 -177.4(3) . . . . ? C9 O4 C6 C5 2.2(5) . . . . ? C7 C5 C6 O3 177.4(3) . . . . ? C4 C5 C6 O3 0.6(5) . . . . ? C7 C5 C6 O4 -2.1(5) . . . . ? C4 C5 C6 O4 -179.0(3) . . . . ? Mg1 O2 C7 C8 174.7(2) . . . . ? Mg1 O2 C7 C5 -5.6(5) . . . . ? C6 C5 C7 O2 -179.3(3) . . . . ? C4 C5 C7 O2 -2.7(6) . . . . ? C6 C5 C7 C8 0.3(5) . . . . ? C4 C5 C7 C8 176.9(3) . . . . ? O2 C7 C8 C9 -179.1(3) . . . . ? C5 C7 C8 C9 1.2(5) . . . . ? C7 C8 C9 O4 -1.2(5) . . . . ? C7 C8 C9 C10 178.5(4) . . . . ? C6 O4 C9 C8 -0.5(5) . . . . ? C6 O4 C9 C10 179.8(3) . . . . ? O2' Mg1' O1' C4' 3.5(3) . . . . ? O2' Mg1' O1' C4' -176.5(3) 3_577 . . . ? O1' Mg1' O1' C4' -64(100) 3_577 . . . ? O5' Mg1' O1' C4' 92.4(3) . . . . ? O5' Mg1' O1' C4' -87.6(3) 3_577 . . . ? O2' Mg1' O2' C7' 75(80) 3_577 . . . ? O1' Mg1' O2' C7' 175.7(3) 3_577 . . . ? O1' Mg1' O2' C7' -4.3(3) . . . . ? O5' Mg1' O2' C7' -94.0(3) . . . . ? O5' Mg1' O2' C7' 86.0(3) 3_577 . . . ? O2' Mg1' O5' C11' 161.6(4) . . . . ? O2' Mg1' O5' C11' -18.4(4) 3_577 . . . ? O1' Mg1' O5' C11' -105.7(4) 3_577 . . . ? O1' Mg1' O5' C11' 74.3(4) . . . . ? O5' Mg1' O5' C11' -31(100) 3_577 . . . ? C6' O3' C2' C3' -3.0(5) . . . . ? C6' O3' C2' C1' 177.2(3) . . . . ? O3' C2' C3' C4' 1.3(5) . . . . ? C1' C2' C3' C4' -179.0(4) . . . . ? Mg1' O1' C4' C3' 178.0(2) . . . . ? Mg1' O1' C4' C5' -2.2(5) . . . . ? C2' C3' C4' O1' -178.4(3) . . . . ? C2' C3' C4' C5' 1.8(5) . . . . ? O1' C4' C5' C6' 177.1(3) . . . . ? C3' C4' C5' C6' -3.2(5) . . . . ? O1' C4' C5' C7' 0.1(5) . . . . ? C3' C4' C5' C7' 179.8(3) . . . . ? C9' O4' C6' O3' -179.2(3) . . . . ? C9' O4' C6' C5' 0.3(5) . . . . ? C2' O3' C6' O4' -179.0(3) . . . . ? C2' O3' C6' C5' 1.5(5) . . . . ? C4' C5' C6' O4' -177.8(3) . . . . ? C7' C5' C6' O4' -0.5(5) . . . . ? C4' C5' C6' O3' 1.7(5) . . . . ? C7' C5' C6' O3' 178.9(3) . . . . ? Mg1' O2' C7' C8' -175.0(2) . . . . ? Mg1' O2' C7' C5' 3.9(5) . . . . ? C6' C5' C7' O2' -177.9(3) . . . . ? C4' C5' C7' O2' -0.9(5) . . . . ? C6' C5' C7' C8' 1.0(5) . . . . ? C4' C5' C7' C8' 178.0(3) . . . . ? O2' C7' C8' C9' 177.5(3) . . . . ? C5' C7' C8' C9' -1.4(5) . . . . ? C7' C8' C9' O4' 1.2(5) . . . . ? C7' C8' C9' C10' -177.4(4) . . . . ? C6' O4' C9' C8' -0.6(5) . . . . ? C6' O4' C9' C10' 178.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5' H5'O O9A 0.93(2) 1.83(3) 2.728(12) 161(4) 1_556 O5' H5'O O8 0.93(2) 1.98(3) 2.832(8) 151(4) 1_556 O5 H5O O1S 0.95(2) 1.73(3) 2.656(4) 165(6) . O1S H1S O7A 1.00(2) 2.02(7) 2.872(19) 142(8) 4_576 O1S H1S O8 1.00(2) 2.12(5) 3.045(10) 154(8) 4_576 O1S H1S O6 1.00(2) 2.67(5) 3.575(7) 151(8) 4_576 O1S H2S O6 0.98(2) 2.07(3) 3.032(6) 164(6) . O1S H2S O8A 0.98(2) 2.55(7) 3.181(14) 122(5) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.697 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.072 # Attachment '7b-jw46.cif' data_jw46 _database_code_depnum_ccdc_archive 'CCDC 774945' #TrackingRef '7b-jw46.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cl2 Ni O18' _chemical_formula_weight 706.02 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.412(2) _cell_length_b 14.508(4) _cell_length_c 13.476(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.849(5) _cell_angle_gamma 90.00 _cell_volume 1441.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2594 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 24.96 _exptl_crystal_description block _exptl_crystal_colour light-green _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7592 _exptl_absorpt_correction_T_max 0.8796 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9624 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3129 _reflns_number_gt 2595 _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. ; _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^)+(0.0504P)^2^+1.0341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3129 _refine_ls_number_parameters 254 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.044 _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 Ni1 Ni 0.0000 0.5000 0.0000 0.02849(15) Uani 1 2 d S . . Cl1 Cl 0.20478(11) 0.34631(6) 0.32635(5) 0.0489(2) Uani 1 1 d D . . O1 O 0.1503(2) 0.38695(11) -0.01935(13) 0.0329(4) Uani 1 1 d . . . O2 O -0.1631(2) 0.42878(11) 0.08309(13) 0.0345(4) Uani 1 1 d . . . O3 O 0.0600(3) 0.12322(12) 0.05950(15) 0.0367(4) Uani 1 1 d . . . O4 O -0.1684(2) 0.15473(11) 0.14059(13) 0.0322(4) Uani 1 1 d . . . O5 O 0.1681(3) 0.53158(15) 0.12844(16) 0.0399(5) Uani 1 1 d . . . O6 O 0.0910(4) 0.42142(19) 0.28830(19) 0.0745(8) Uani 1 1 d D A . O7 O 0.1665(4) 0.3289(2) 0.42745(19) 0.0632(8) Uani 0.851(3) 1 d PD A 1 O8 O 0.1663(6) 0.2640(3) 0.2718(3) 0.1031(15) Uani 0.851(3) 1 d PD A 1 O9 O 0.3906(4) 0.3688(2) 0.3287(3) 0.0806(11) Uani 0.851(3) 1 d PD A 1 O7A O 0.287(2) 0.3319(13) 0.2323(10) 0.0632(8) Uani 0.149(3) 1 d PD A 2 O8A O 0.303(4) 0.3684(17) 0.4107(17) 0.1031(15) Uani 0.149(3) 1 d PD A 2 O9A O 0.083(2) 0.2702(13) 0.3181(19) 0.0806(11) Uani 0.149(3) 1 d PD A 2 C1 C 0.2855(6) 0.0603(2) -0.0301(4) 0.0616(11) Uani 1 1 d . . . C2 C 0.1968(4) 0.14485(17) 0.0015(2) 0.0364(6) Uani 1 1 d . . . C3 C 0.2292(4) 0.23228(17) -0.0218(2) 0.0319(6) Uani 1 1 d . . . C4 C 0.1188(3) 0.30685(16) 0.00624(18) 0.0278(5) Uani 1 1 d . . . C5 C -0.0301(3) 0.28117(15) 0.06351(17) 0.0254(5) Uani 1 1 d . . . C6 C -0.0454(3) 0.19047(16) 0.08651(17) 0.0270(5) Uani 1 1 d . . . C7 C -0.1606(3) 0.34391(16) 0.09967(18) 0.0285(5) Uani 1 1 d . . . C8 C -0.2935(4) 0.30262(18) 0.15612(19) 0.0337(6) Uani 1 1 d . . . C9 C -0.2960(4) 0.21208(17) 0.17495(19) 0.0326(6) Uani 1 1 d . . . C10 C -0.4222(5) 0.1590(2) 0.2306(3) 0.0449(8) Uani 1 1 d . . . C11 C 0.3618(5) 0.5419(3) 0.1316(3) 0.0591(9) Uani 1 1 d . . . H1A H 0.381(6) 0.076(3) -0.060(3) 0.071(12) Uiso 1 1 d . . . H1B H 0.318(7) 0.023(3) 0.027(4) 0.099(16) Uiso 1 1 d . . . H1C H 0.206(7) 0.025(3) -0.078(4) 0.097(16) Uiso 1 1 d . . . H3 H 0.318(5) 0.243(2) -0.059(2) 0.052(9) Uiso 1 1 d . . . H5 H 0.148(5) 0.499(2) 0.166(3) 0.037(10) Uiso 1 1 d . . . H8 H -0.375(4) 0.340(2) 0.182(2) 0.045(8) Uiso 1 1 d . . . H10A H -0.507(5) 0.194(3) 0.252(3) 0.061(11) Uiso 1 1 d . . . H10B H -0.476(5) 0.116(3) 0.186(3) 0.068(11) Uiso 1 1 d . . . H10C H -0.355(5) 0.131(2) 0.288(3) 0.058(10) Uiso 1 1 d . . . H11A H 0.391(6) 0.599(3) 0.105(3) 0.091(15) Uiso 1 1 d . . . H11B H 0.417(6) 0.546(3) 0.197(4) 0.097(15) Uiso 1 1 d . . . H11C H 0.408(8) 0.493(4) 0.098(5) 0.13(2) Uiso 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 Ni1 0.0387(3) 0.0181(2) 0.0308(3) 0.00196(17) 0.0135(2) 0.00189(18) Cl1 0.0466(5) 0.0575(5) 0.0423(4) -0.0008(3) 0.0023(3) 0.0179(3) O1 0.0407(10) 0.0209(8) 0.0397(10) 0.0027(7) 0.0162(8) 0.0015(7) O2 0.0434(11) 0.0221(8) 0.0407(10) 0.0045(7) 0.0178(8) 0.0030(8) O3 0.0369(10) 0.0232(8) 0.0518(11) 0.0051(8) 0.0133(9) 0.0019(7) O4 0.0391(11) 0.0242(8) 0.0345(9) 0.0029(7) 0.0103(8) -0.0018(7) O5 0.0474(13) 0.0370(11) 0.0364(11) -0.0002(9) 0.0085(9) 0.0008(9) O6 0.0720(17) 0.0939(19) 0.0621(15) 0.0390(14) 0.0279(13) 0.0432(15) O7 0.0599(19) 0.086(2) 0.0434(14) 0.0211(14) 0.0030(13) 0.0251(16) O8 0.109(3) 0.103(3) 0.087(3) -0.047(2) -0.037(2) 0.030(2) O9 0.0488(18) 0.091(2) 0.105(3) 0.014(2) 0.0214(18) 0.0111(16) O7A 0.0599(19) 0.086(2) 0.0434(14) 0.0211(14) 0.0030(13) 0.0251(16) O8A 0.109(3) 0.103(3) 0.087(3) -0.047(2) -0.037(2) 0.030(2) O9A 0.0488(18) 0.091(2) 0.105(3) 0.014(2) 0.0214(18) 0.0111(16) C1 0.058(2) 0.0290(15) 0.104(3) 0.0041(19) 0.036(2) 0.0097(16) C2 0.0293(14) 0.0277(13) 0.0541(16) 0.0049(12) 0.0127(12) 0.0040(10) C3 0.0286(14) 0.0247(12) 0.0441(15) 0.0008(11) 0.0124(12) 0.0023(10) C4 0.0302(13) 0.0242(11) 0.0291(12) 0.0002(9) 0.0033(10) -0.0009(10) C5 0.0294(13) 0.0236(11) 0.0232(11) 0.0006(9) 0.0026(9) -0.0015(9) C6 0.0281(13) 0.0245(11) 0.0284(12) 0.0002(9) 0.0033(10) -0.0004(10) C7 0.0342(14) 0.0247(11) 0.0272(12) 0.0015(9) 0.0066(10) 0.0008(10) C8 0.0405(16) 0.0283(12) 0.0346(13) 0.0011(11) 0.0155(12) 0.0014(11) C9 0.0376(15) 0.0318(13) 0.0298(12) -0.0003(10) 0.0101(11) -0.0009(11) C10 0.057(2) 0.0344(15) 0.0476(18) 0.0012(14) 0.0250(17) -0.0062(15) C11 0.051(2) 0.065(2) 0.061(2) 0.005(2) -0.0008(18) -0.0082(19) _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 Ni1 O1 2.0143(17) 3_565 ? Ni1 O1 2.0143(17) . ? Ni1 O2 2.0146(17) . ? Ni1 O2 2.0146(17) 3_565 ? Ni1 O5 2.078(2) 3_565 ? Ni1 O5 2.078(2) . ? Cl1 O8A 1.325(14) . ? Cl1 O9 1.412(3) . ? Cl1 O8 1.416(4) . ? Cl1 O9A 1.423(16) . ? Cl1 O6 1.440(2) . ? Cl1 O7 1.442(3) . ? Cl1 O7A 1.476(13) . ? O1 C4 1.241(3) . ? O2 C7 1.251(3) . ? O3 C6 1.324(3) . ? O3 C2 1.378(3) . ? O4 C6 1.329(3) . ? O4 C9 1.375(3) . ? O5 C11 1.440(4) . ? O5 H5 0.73(3) . ? C1 C2 1.475(4) . ? C1 H1A 0.88(4) . ? C1 H1B 0.95(5) . ? C1 H1C 0.97(5) . ? C2 C3 1.334(4) . ? C3 C4 1.430(3) . ? C3 H3 0.88(3) . ? C4 C5 1.458(3) . ? C5 C6 1.359(3) . ? C5 C7 1.448(3) . ? C7 C8 1.435(4) . ? C8 C9 1.338(4) . ? C8 H8 0.91(3) . ? C9 C10 1.474(4) . ? C10 H10A 0.87(4) . ? C10 H10B 0.92(4) . ? C10 H10C 0.97(4) . ? C11 H11A 0.93(5) . ? C11 H11B 0.94(5) . ? C11 H11C 0.93(6) . ? 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 Ni1 O1 180.00(10) 3_565 . ? O1 Ni1 O2 88.55(7) 3_565 . ? O1 Ni1 O2 91.45(7) . . ? O1 Ni1 O2 91.45(7) 3_565 3_565 ? O1 Ni1 O2 88.55(7) . 3_565 ? O2 Ni1 O2 180.00(8) . 3_565 ? O1 Ni1 O5 89.70(8) 3_565 3_565 ? O1 Ni1 O5 90.30(8) . 3_565 ? O2 Ni1 O5 90.40(9) . 3_565 ? O2 Ni1 O5 89.60(9) 3_565 3_565 ? O1 Ni1 O5 90.30(8) 3_565 . ? O1 Ni1 O5 89.70(8) . . ? O2 Ni1 O5 89.60(9) . . ? O2 Ni1 O5 90.40(9) 3_565 . ? O5 Ni1 O5 180.0 3_565 . ? O8A Cl1 O9 58.4(15) . . ? O8A Cl1 O8 135.5(10) . . ? O9 Cl1 O8 110.6(3) . . ? O8A Cl1 O9A 122.9(17) . . ? O9 Cl1 O9A 142.2(8) . . ? O8 Cl1 O9A 38.0(9) . . ? O8A Cl1 O6 111.9(10) . . ? O9 Cl1 O6 111.56(19) . . ? O8 Cl1 O6 112.0(2) . . ? O9A Cl1 O6 102.4(9) . . ? O8A Cl1 O7 51.4(15) . . ? O9 Cl1 O7 107.7(2) . . ? O8 Cl1 O7 107.1(3) . . ? O9A Cl1 O7 75.8(10) . . ? O6 Cl1 O7 107.72(15) . . ? O8A Cl1 O7A 122.1(16) . . ? O9 Cl1 O7A 64.2(7) . . ? O8 Cl1 O7A 61.0(8) . . ? O9A Cl1 O7A 97.9(12) . . ? O6 Cl1 O7A 94.5(6) . . ? O7 Cl1 O7A 157.6(6) . . ? C4 O1 Ni1 127.19(16) . . ? C7 O2 Ni1 127.25(16) . . ? C6 O3 C2 118.49(19) . . ? C6 O4 C9 118.83(19) . . ? C11 O5 Ni1 124.0(2) . . ? C11 O5 H5 109(3) . . ? Ni1 O5 H5 107(3) . . ? C2 C1 H1A 109(3) . . ? C2 C1 H1B 109(3) . . ? H1A C1 H1B 112(4) . . ? C2 C1 H1C 112(3) . . ? H1A C1 H1C 107(4) . . ? H1B C1 H1C 109(4) . . ? C3 C2 O3 120.7(2) . . ? C3 C2 C1 128.8(3) . . ? O3 C2 C1 110.5(2) . . ? C2 C3 C4 122.4(2) . . ? C2 C3 H3 118(2) . . ? C4 C3 H3 120(2) . . ? O1 C4 C3 120.4(2) . . ? O1 C4 C5 124.1(2) . . ? C3 C4 C5 115.5(2) . . ? C6 C5 C7 117.2(2) . . ? C6 C5 C4 116.9(2) . . ? C7 C5 C4 125.8(2) . . ? O3 C6 O4 108.7(2) . . ? O3 C6 C5 125.8(2) . . ? O4 C6 C5 125.5(2) . . ? O2 C7 C8 120.5(2) . . ? O2 C7 C5 123.8(2) . . ? C8 C7 C5 115.7(2) . . ? C9 C8 C7 122.2(2) . . ? C9 C8 H8 119.6(19) . . ? C7 C8 H8 118.1(19) . . ? C8 C9 O4 120.5(2) . . ? C8 C9 C10 129.1(3) . . ? O4 C9 C10 110.4(2) . . ? C9 C10 H10A 112(2) . . ? C9 C10 H10B 106(2) . . ? H10A C10 H10B 109(3) . . ? C9 C10 H10C 109(2) . . ? H10A C10 H10C 108(3) . . ? H10B C10 H10C 113(3) . . ? O5 C11 H11A 111(3) . . ? O5 C11 H11B 112(3) . . ? H11A C11 H11B 102(4) . . ? O5 C11 H11C 109(4) . . ? H11A C11 H11C 112(4) . . ? H11B C11 H11C 111(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 O1 C4 176(68) 3_565 . . . ? O2 Ni1 O1 C4 7.0(2) . . . . ? O2 Ni1 O1 C4 -173.0(2) 3_565 . . . ? O5 Ni1 O1 C4 -83.4(2) 3_565 . . . ? O5 Ni1 O1 C4 96.6(2) . . . . ? O1 Ni1 O2 C7 174.2(2) 3_565 . . . ? O1 Ni1 O2 C7 -5.8(2) . . . . ? O2 Ni1 O2 C7 18(100) 3_565 . . . ? O5 Ni1 O2 C7 84.5(2) 3_565 . . . ? O5 Ni1 O2 C7 -95.5(2) . . . . ? O1 Ni1 O5 C11 -124.7(3) 3_565 . . . ? O1 Ni1 O5 C11 55.3(3) . . . . ? O2 Ni1 O5 C11 146.8(3) . . . . ? O2 Ni1 O5 C11 -33.2(3) 3_565 . . . ? O5 Ni1 O5 C11 36(13) 3_565 . . . ? C6 O3 C2 C3 4.0(4) . . . . ? C6 O3 C2 C1 -173.7(3) . . . . ? O3 C2 C3 C4 -4.0(4) . . . . ? C1 C2 C3 C4 173.3(4) . . . . ? Ni1 O1 C4 C3 173.68(18) . . . . ? Ni1 O1 C4 C5 -5.1(3) . . . . ? C2 C3 C4 O1 -177.9(3) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? O1 C4 C5 C6 -179.4(2) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? O1 C4 C5 C7 -0.7(4) . . . . ? C3 C4 C5 C7 -179.6(2) . . . . ? C2 O3 C6 O4 179.3(2) . . . . ? C2 O3 C6 C5 -1.1(4) . . . . ? C9 O4 C6 O3 -178.5(2) . . . . ? C9 O4 C6 C5 1.9(4) . . . . ? C7 C5 C6 O3 179.4(2) . . . . ? C4 C5 C6 O3 -1.8(4) . . . . ? C7 C5 C6 O4 -1.0(4) . . . . ? C4 C5 C6 O4 177.8(2) . . . . ? Ni1 O2 C7 C8 -176.37(18) . . . . ? Ni1 O2 C7 C5 2.6(4) . . . . ? C6 C5 C7 O2 -179.3(2) . . . . ? C4 C5 C7 O2 2.1(4) . . . . ? C6 C5 C7 C8 -0.2(3) . . . . ? C4 C5 C7 C8 -178.9(2) . . . . ? O2 C7 C8 C9 179.6(3) . . . . ? C5 C7 C8 C9 0.6(4) . . . . ? C7 C8 C9 O4 0.3(4) . . . . ? C7 C8 C9 C10 -179.6(3) . . . . ? C6 O4 C9 C8 -1.5(4) . . . . ? C6 O4 C9 C10 178.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O6 0.73(3) 2.07(3) 2.788(3) 172(3) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.733 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.067 # Attachment '8-jw59.cif' data_jw59 _database_code_depnum_ccdc_archive 'CCDC 774946' #TrackingRef '8-jw59.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32.50 H32 Cl2 Li2 O22.50' _chemical_formula_weight 867.36 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' Li Li -0.0003 0.0001 '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' Cl Cl 0.1484 0.1585 '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 13.6532(18) _cell_length_b 15.954(2) _cell_length_c 18.398(2) _cell_angle_alpha 79.690(2) _cell_angle_beta 87.173(2) _cell_angle_gamma 76.390(2) _cell_volume 3832.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3870 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1788 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9078 _exptl_absorpt_correction_T_max 0.9597 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37382 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 13455 _reflns_number_gt 8426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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 crystal structure two of five solvent molecules, CH3OH, are highly disordered and were treated by SQUEEZE [Van der Sluis,P. & Spek, A.L. (1990) Acta Cryst., Sect.A,A46,194-201.]. Corrections of the X-ray data by SQUEEZE (67 electron/cell) was close to the required values (72 electron/cell). ; _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^)+(0.0799P)^2^+0.2693P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13455 _refine_ls_number_parameters 1219 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1691 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Li1 Li 0.2479(4) 0.3394(4) 0.2050(3) 0.0343(14) Uani 1 1 d . . . Li2 Li 0.4698(4) 0.2975(4) 0.2007(3) 0.0330(14) Uani 1 1 d . . . O1 O 0.36744(17) 0.33505(16) 0.12607(12) 0.0361(6) Uani 1 1 d . . . O2 O 0.16247(18) 0.3354(2) 0.12269(14) 0.0562(8) Uani 1 1 d . . . O3 O 0.34205(15) 0.41780(14) -0.09567(11) 0.0253(5) Uani 1 1 d . . . O4 O 0.18608(16) 0.41154(14) -0.09879(12) 0.0268(5) Uani 1 1 d . . . O5 O 0.36956(16) 0.28336(15) 0.27756(12) 0.0307(6) Uani 1 1 d . . . O6 O 0.16413(17) 0.28272(16) 0.28171(12) 0.0365(6) Uani 1 1 d . . . O7 O 0.38283(16) 0.12659(14) 0.47825(12) 0.0266(5) Uani 1 1 d . . . O8 O 0.22765(16) 0.11805(15) 0.47742(12) 0.0307(6) Uani 1 1 d . . . O9 O 0.57444(16) 0.35359(14) 0.21101(12) 0.0315(6) Uani 1 1 d . . . O10 O 0.55605(17) 0.18705(15) 0.18909(13) 0.0342(6) Uani 1 1 d . . . O11 O 0.87570(16) 0.25790(14) 0.18770(12) 0.0277(5) Uani 1 1 d . . . O12 O 0.86088(16) 0.13259(14) 0.16840(12) 0.0288(5) Uani 1 1 d . . . O13 O 0.2254(2) 0.46550(18) 0.20289(15) 0.0600(8) Uani 1 1 d D . . H13A H 0.2155 0.5004 0.1551 0.072 Uiso 1 1 calc RD . . C1 C 0.5090(3) 0.4347(3) -0.1139(2) 0.0335(9) Uani 1 1 d . . . C2 C 0.4324(2) 0.4075(2) -0.06111(18) 0.0246(7) Uani 1 1 d . . . C3 C 0.4422(3) 0.3775(2) 0.0116(2) 0.0295(8) Uani 1 1 d . . . C4 C 0.3595(2) 0.3589(2) 0.05738(19) 0.0286(8) Uani 1 1 d . . . C5 C 0.2658(2) 0.3704(2) 0.01928(18) 0.0282(8) Uani 1 1 d . . . C6 C 0.2646(2) 0.3986(2) -0.05492(17) 0.0244(7) Uani 1 1 d . . . C7 C 0.1723(3) 0.3557(3) 0.0551(2) 0.0388(9) Uani 1 1 d . . . C8 C 0.0901(3) 0.3674(3) 0.0046(2) 0.0362(9) Uani 1 1 d . . . C9 C 0.0972(2) 0.3939(2) -0.06726(19) 0.0294(8) Uani 1 1 d . . . C10 C 0.0175(3) 0.4110(3) -0.1236(2) 0.0342(9) Uani 1 1 d . . . C11 C 0.5456(3) 0.1364(3) 0.5073(2) 0.0322(9) Uani 1 1 d . . . C12 C 0.4638(2) 0.1626(2) 0.45205(18) 0.0267(8) Uani 1 1 d . . . C13 C 0.4603(2) 0.2135(2) 0.38631(19) 0.0274(8) Uani 1 1 d . . . C14 C 0.3715(2) 0.2385(2) 0.34037(18) 0.0253(7) Uani 1 1 d . . . C15 C 0.2857(2) 0.2069(2) 0.37305(17) 0.0231(7) Uani 1 1 d . . . C16 C 0.2976(2) 0.1537(2) 0.43963(18) 0.0255(8) Uani 1 1 d . . . C17 C 0.1850(3) 0.2325(2) 0.34068(19) 0.0302(8) Uani 1 1 d . . . C18 C 0.1102(3) 0.1944(3) 0.3844(2) 0.0351(9) Uani 1 1 d . . . C19 C 0.1310(3) 0.1404(2) 0.44867(19) 0.0331(8) Uani 1 1 d . . . C20 C 0.0620(4) 0.0968(4) 0.4988(3) 0.0494(12) Uani 1 1 d . . . C21 C 0.9218(3) 0.3834(3) 0.2098(3) 0.0406(10) Uani 1 1 d . . . C22 C 0.8383(3) 0.3412(2) 0.20400(17) 0.0274(8) Uani 1 1 d . . . C23 C 0.7400(3) 0.3721(2) 0.21205(19) 0.0276(8) Uani 1 1 d . . . C24 C 0.6671(2) 0.3229(2) 0.20473(17) 0.0261(8) Uani 1 1 d . . . C25 C 0.7084(2) 0.2354(2) 0.18922(16) 0.0234(7) Uani 1 1 d . . . C26 C 0.8100(2) 0.2101(2) 0.18209(17) 0.0244(7) Uani 1 1 d . . . C27 C 0.6497(2) 0.1712(2) 0.18390(17) 0.0276(8) Uani 1 1 d . . . C28 C 0.7086(3) 0.0871(2) 0.17262(18) 0.0286(8) Uani 1 1 d . . . C29 C 0.8080(3) 0.0692(2) 0.16524(18) 0.0283(8) Uani 1 1 d . . . C30 C 0.8782(3) -0.0134(3) 0.1538(3) 0.0361(9) Uani 1 1 d . . . C31 C 0.2217(5) 0.5119(3) 0.2602(2) 0.099(2) Uani 1 1 d . . . H31A H 0.2085 0.5747 0.2402 0.148 Uiso 1 1 calc R . . H31B H 0.2864 0.4938 0.2861 0.148 Uiso 1 1 calc R . . H31C H 0.1677 0.5002 0.2948 0.148 Uiso 1 1 calc R . . Li1' Li 0.2518(4) 0.7343(4) 0.3034(3) 0.0420(16) Uani 1 1 d . . . Li2' Li 0.0407(4) 0.7246(4) 0.3027(3) 0.0346(14) Uani 1 1 d . . . O1' O 0.14875(16) 0.68156(16) 0.37367(12) 0.0342(6) Uani 1 1 d . . . O2' O 0.35351(18) 0.68127(19) 0.38104(13) 0.0489(7) Uani 1 1 d . . . O3' O 0.17408(15) 0.57513(14) 0.59175(11) 0.0247(5) Uani 1 1 d . . . O4' O 0.33111(16) 0.57689(14) 0.59757(11) 0.0264(5) Uani 1 1 d . . . O5' O 0.13742(16) 0.74385(15) 0.22472(12) 0.0332(6) Uani 1 1 d . . . O6' O 0.34551(17) 0.73793(17) 0.21738(13) 0.0419(7) Uani 1 1 d . . . O7' O 0.12928(16) 0.87630(14) 0.01400(12) 0.0262(5) Uani 1 1 d . . . O8' O 0.28699(16) 0.87783(15) 0.01056(12) 0.0327(6) Uani 1 1 d . . . O9' O -0.04996(17) 0.82950(15) 0.32102(13) 0.0348(6) Uani 1 1 d . . . O10' O -0.06102(16) 0.66377(14) 0.29110(12) 0.0319(6) Uani 1 1 d . . . O11' O -0.35571(16) 0.87880(14) 0.33057(13) 0.0324(6) Uani 1 1 d . . . O12' O -0.36435(16) 0.75367(14) 0.30676(12) 0.0309(6) Uani 1 1 d . . . O13' O 0.2091(2) 0.85919(19) 0.31042(15) 0.0616(8) Uani 1 1 d D . . H13B H 0.2060 0.9013 0.2665 0.074 Uiso 1 1 calc RD . . C1' C 0.0053(3) 0.5598(3) 0.6061(2) 0.0334(9) Uani 1 1 d . . . C2' C 0.0840(2) 0.5889(2) 0.55570(18) 0.0270(8) Uani 1 1 d . . . C3' C 0.0742(3) 0.6254(2) 0.48429(19) 0.0298(8) Uani 1 1 d . . . C4' C 0.1569(2) 0.6487(2) 0.44079(18) 0.0278(8) Uani 1 1 d . . . C5' C 0.2510(2) 0.6326(2) 0.47992(18) 0.0271(8) Uani 1 1 d . . . C6' C 0.2518(2) 0.5966(2) 0.55276(17) 0.0244(7) Uani 1 1 d . . . C7' C 0.3452(3) 0.6503(2) 0.44679(19) 0.0326(8) Uani 1 1 d . . . C8' C 0.4297(3) 0.6267(2) 0.4968(2) 0.0329(9) Uani 1 1 d . . . C9' C 0.4217(2) 0.5921(2) 0.56785(18) 0.0276(8) Uani 1 1 d . . . C10' C 0.5021(3) 0.5639(3) 0.6243(2) 0.0327(9) Uani 1 1 d . . . C11' C -0.0376(3) 0.8725(3) -0.0089(2) 0.0375(10) Uani 1 1 d . . . C12' C 0.0456(2) 0.8479(2) 0.04512(18) 0.0261(8) Uani 1 1 d . . . C13' C 0.0477(2) 0.8039(2) 0.11422(19) 0.0268(8) Uani 1 1 d . . . C14' C 0.1364(2) 0.7816(2) 0.15926(18) 0.0265(8) Uani 1 1 d . . . C15' C 0.2254(2) 0.8053(2) 0.12264(17) 0.0250(7) Uani 1 1 d . . . C16' C 0.2150(2) 0.8507(2) 0.05264(18) 0.0242(7) Uani 1 1 d . . . C17' C 0.3269(3) 0.7796(2) 0.15454(19) 0.0328(8) Uani 1 1 d . . . C18' C 0.4035(3) 0.8080(3) 0.1061(2) 0.0357(9) Uani 1 1 d . . . C19' C 0.3840(3) 0.8552(2) 0.03871(19) 0.0355(9) Uani 1 1 d . . . C20' C 0.4550(3) 0.8897(4) -0.0157(3) 0.0473(12) Uani 1 1 d . . . C21' C -0.3775(3) 1.0226(3) 0.3532(3) 0.0392(10) Uani 1 1 d . . . C22' C -0.3050(3) 0.9417(2) 0.33958(18) 0.0313(8) Uani 1 1 d . . . C23' C -0.2060(3) 0.9266(2) 0.33575(18) 0.0305(8) Uani 1 1 d . . . C24' C -0.1440(3) 0.8434(2) 0.32314(17) 0.0282(8) Uani 1 1 d . . . C25' C -0.1995(2) 0.7797(2) 0.31201(17) 0.0247(7) Uani 1 1 d . . . C26' C -0.3016(3) 0.8026(2) 0.31649(17) 0.0279(8) Uani 1 1 d . . . C27' C -0.1542(3) 0.6922(2) 0.29615(17) 0.0275(8) Uani 1 1 d . . . C28' C -0.2250(3) 0.6420(2) 0.28554(19) 0.0299(8) Uani 1 1 d . . . C29' C -0.3236(3) 0.6709(2) 0.29139(18) 0.0278(8) Uani 1 1 d . . . C30' C -0.4054(3) 0.6268(3) 0.2831(3) 0.0420(10) Uani 1 1 d . . . C31' C 0.1828(5) 0.8885(4) 0.3780(3) 0.108(2) Uani 1 1 d . . . H31D H 0.1650 0.9527 0.3694 0.162 Uiso 1 1 calc R . . H31E H 0.2402 0.8671 0.4117 0.162 Uiso 1 1 calc R . . H31F H 0.1251 0.8662 0.3999 0.162 Uiso 1 1 calc R . . Cl1 Cl 0.22791(6) 0.62144(6) 0.99832(5) 0.0318(2) Uani 1 1 d . . . Cl2 Cl 0.70694(6) 0.83001(6) 0.10828(5) 0.0346(2) Uani 1 1 d . . . Cl3 Cl 0.73919(6) 0.63039(5) 0.49154(4) 0.0295(2) Uani 1 1 d . . . Cl4 Cl 0.80130(6) 0.17864(6) 0.38691(5) 0.0302(2) Uani 1 1 d . . . O14 O 0.23297(19) 0.60236(17) 1.07783(13) 0.0445(7) Uani 1 1 d . . . O15 O 0.1920(3) 0.71196(17) 0.97507(15) 0.0652(9) Uani 1 1 d . . . O16 O 0.32399(18) 0.59072(19) 0.96716(15) 0.0513(7) Uani 1 1 d . . . O17 O 0.1586(2) 0.5766(2) 0.97374(16) 0.0596(8) Uani 1 1 d . . . O18 O 0.7075(3) 0.8808(3) 0.0383(2) 0.1257(19) Uani 1 1 d . . . O19 O 0.6587(2) 0.8859(2) 0.1585(2) 0.0818(11) Uani 1 1 d . . . O20 O 0.6515(2) 0.76579(18) 0.1091(2) 0.0735(10) Uani 1 1 d . . . O21 O 0.80830(17) 0.79003(16) 0.13193(14) 0.0412(6) Uani 1 1 d . . . O22 O 0.6968(2) 0.72107(16) 0.46903(14) 0.0540(8) Uani 1 1 d . . . O23 O 0.83777(17) 0.60660(18) 0.46007(14) 0.0470(7) Uani 1 1 d . . . O24 O 0.67527(19) 0.58225(18) 0.46527(15) 0.0523(7) Uani 1 1 d . . . O25 O 0.74342(19) 0.60962(17) 0.57053(13) 0.0445(7) Uani 1 1 d . . . O26 O 0.7990(2) 0.1202(2) 0.45403(15) 0.0734(10) Uani 1 1 d . . . O27 O 0.8587(2) 0.23946(19) 0.3937(2) 0.0758(11) Uani 1 1 d . . . O28 O 0.8474(2) 0.12821(18) 0.33238(15) 0.0567(8) Uani 1 1 d . . . O29 O 0.70058(17) 0.22404(16) 0.36529(14) 0.0429(7) Uani 1 1 d . . . O1S O 0.1313(3) 0.9984(2) 0.1992(2) 0.0860(11) Uani 1 1 d . . . C1S C 0.0960(5) 1.0764(4) 0.2337(4) 0.115(2) Uani 1 1 d . . . H1A H 0.479(3) 0.491(3) -0.138(2) 0.055(13) Uiso 1 1 d . . . H1B H 0.569(2) 0.4349(19) -0.0884(17) 0.025(9) Uiso 1 1 d . . . H1C H 0.527(3) 0.405(2) -0.154(2) 0.047(12) Uiso 1 1 d . . . H1D H -0.014(3) 0.591(3) 0.644(2) 0.061(14) Uiso 1 1 d . . . H1E H 0.034(3) 0.497(3) 0.632(2) 0.053(12) Uiso 1 1 d . . . H1F H -0.057(3) 0.568(2) 0.576(2) 0.048(11) Uiso 1 1 d . . . H3 H 0.498(2) 0.375(2) 0.0286(17) 0.023(9) Uiso 1 1 d . . . H3' H 0.007(2) 0.6352(19) 0.4611(17) 0.027(9) Uiso 1 1 d . . . H8 H 0.034(3) 0.360(2) 0.019(2) 0.045(12) Uiso 1 1 d . . . H8' H 0.492(3) 0.635(2) 0.4797(17) 0.029(9) Uiso 1 1 d . . . H10A H -0.031(3) 0.389(3) -0.105(2) 0.054(13) Uiso 1 1 d . . . H10B H -0.007(2) 0.477(2) -0.1390(17) 0.025(9) Uiso 1 1 d . . . H10C H 0.046(3) 0.384(2) -0.169(2) 0.059(12) Uiso 1 1 d . . . H10D H 0.481(3) 0.585(2) 0.672(2) 0.042(11) Uiso 1 1 d . . . H10E H 0.557(3) 0.580(2) 0.6082(17) 0.027(9) Uiso 1 1 d . . . H10F H 0.520(2) 0.497(2) 0.6400(17) 0.029(9) Uiso 1 1 d . . . H11A H 0.563(2) 0.072(2) 0.5230(16) 0.020(8) Uiso 1 1 d . . . H11B H 0.527(2) 0.158(2) 0.553(2) 0.034(10) Uiso 1 1 d . . . H11C H 0.603(3) 0.155(2) 0.4889(18) 0.037(10) Uiso 1 1 d . . . H11D H -0.092(3) 0.856(3) 0.009(2) 0.053(13) Uiso 1 1 d . . . H11E H -0.053(3) 0.933(3) -0.027(2) 0.072(15) Uiso 1 1 d . . . H11F H -0.017(3) 0.846(3) -0.050(2) 0.059(13) Uiso 1 1 d . . . H13 H 0.518(3) 0.233(2) 0.3713(19) 0.041(10) Uiso 1 1 d . . . H13' H -0.014(3) 0.790(2) 0.1297(19) 0.039(10) Uiso 1 1 d . . . H18 H 0.045(3) 0.209(2) 0.368(2) 0.048(11) Uiso 1 1 d . . . H18' H 0.470(3) 0.797(2) 0.1254(19) 0.038(10) Uiso 1 1 d . . . H20A H 0.051(3) 0.120(3) 0.540(2) 0.049(14) Uiso 1 1 d . . . H20B H 0.094(4) 0.037(3) 0.511(3) 0.087(18) Uiso 1 1 d . . . H20C H -0.003(3) 0.107(2) 0.478(2) 0.054(12) Uiso 1 1 d . . . H20D H 0.460(3) 0.863(3) -0.054(3) 0.068(16) Uiso 1 1 d . . . H20E H 0.523(3) 0.883(2) 0.0045(19) 0.045(11) Uiso 1 1 d . . . H20F H 0.434(3) 0.952(3) -0.028(3) 0.078(17) Uiso 1 1 d . . . H21A H 0.954(3) 0.390(3) 0.171(2) 0.054(15) Uiso 1 1 d . . . H21B H 0.971(3) 0.351(2) 0.2448(19) 0.035(10) Uiso 1 1 d . . . H21C H 0.895(2) 0.440(2) 0.2271(18) 0.033(10) Uiso 1 1 d . . . H21D H -0.419(3) 1.046(2) 0.3166(19) 0.030(11) Uiso 1 1 d . . . H21E H -0.343(3) 1.067(3) 0.366(2) 0.054(12) Uiso 1 1 d . . . H21F H -0.425(3) 1.012(2) 0.393(2) 0.037(10) Uiso 1 1 d . . . H23 H 0.726(2) 0.424(2) 0.2227(16) 0.016(8) Uiso 1 1 d . . . H23' H -0.168(3) 0.971(2) 0.3436(19) 0.049(11) Uiso 1 1 d . . . H28 H 0.677(2) 0.041(2) 0.1731(16) 0.024(9) Uiso 1 1 d . . . H28' H -0.202(2) 0.591(2) 0.2773(18) 0.028(10) Uiso 1 1 d . . . H30A H 0.925(3) -0.033(2) 0.194(2) 0.054(13) Uiso 1 1 d . . . H30B H 0.908(3) -0.004(3) 0.109(3) 0.066(14) Uiso 1 1 d . . . H30C H 0.843(3) -0.055(3) 0.155(2) 0.049(12) Uiso 1 1 d . . . H30D H -0.454(4) 0.625(3) 0.328(3) 0.086(16) Uiso 1 1 d . . . H30E H -0.456(4) 0.659(3) 0.248(3) 0.11(2) Uiso 1 1 d . . . H30F H -0.378(3) 0.572(2) 0.2709(19) 0.039(11) Uiso 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 Li1 0.024(3) 0.047(4) 0.028(3) 0.003(3) 0.000(3) -0.006(3) Li2 0.025(3) 0.043(4) 0.027(3) -0.002(3) 0.000(2) -0.004(3) O1 0.0270(13) 0.0515(16) 0.0243(14) 0.0014(11) -0.0029(11) -0.0033(12) O2 0.0296(15) 0.114(3) 0.0236(15) 0.0009(15) 0.0038(12) -0.0242(16) O3 0.0209(12) 0.0291(13) 0.0245(12) -0.0027(10) -0.0008(10) -0.0042(10) O4 0.0209(12) 0.0353(14) 0.0244(13) -0.0052(10) -0.0035(10) -0.0065(10) O5 0.0235(13) 0.0399(14) 0.0238(13) 0.0020(11) 0.0020(10) -0.0035(11) O6 0.0245(13) 0.0502(16) 0.0280(14) 0.0077(12) -0.0042(11) -0.0055(12) O7 0.0209(12) 0.0288(13) 0.0280(13) 0.0006(10) -0.0035(10) -0.0050(10) O8 0.0244(13) 0.0367(14) 0.0295(13) 0.0054(11) -0.0027(10) -0.0121(11) O9 0.0223(13) 0.0320(14) 0.0361(14) -0.0051(11) 0.0018(11) 0.0009(11) O10 0.0229(13) 0.0364(14) 0.0425(15) -0.0053(12) -0.0013(11) -0.0061(11) O11 0.0226(12) 0.0264(13) 0.0319(13) -0.0020(10) 0.0002(10) -0.0038(10) O12 0.0256(13) 0.0248(13) 0.0333(14) -0.0053(10) 0.0041(10) -0.0013(10) O13 0.082(2) 0.0451(17) 0.0385(17) 0.0078(14) 0.0019(15) 0.0012(16) C1 0.025(2) 0.043(3) 0.032(2) -0.002(2) -0.0031(18) -0.0086(18) C2 0.0167(17) 0.0217(18) 0.033(2) -0.0050(15) -0.0018(14) 0.0000(14) C3 0.0214(19) 0.034(2) 0.031(2) -0.0064(16) -0.0056(16) -0.0021(16) C4 0.0234(18) 0.0298(19) 0.028(2) -0.0030(15) 0.0006(15) 0.0017(15) C5 0.0234(18) 0.034(2) 0.0251(19) -0.0050(15) 0.0000(15) -0.0031(15) C6 0.0220(18) 0.0231(18) 0.0270(19) -0.0042(14) -0.0005(15) -0.0032(14) C7 0.029(2) 0.057(3) 0.028(2) -0.0021(18) -0.0014(16) -0.0096(19) C8 0.022(2) 0.057(3) 0.032(2) -0.0069(18) 0.0023(17) -0.0139(19) C9 0.0212(18) 0.033(2) 0.035(2) -0.0076(16) 0.0009(15) -0.0066(15) C10 0.025(2) 0.048(3) 0.033(2) -0.008(2) -0.0031(17) -0.0129(19) C11 0.024(2) 0.042(3) 0.028(2) -0.0007(18) -0.0022(17) -0.0081(18) C12 0.0213(18) 0.0282(19) 0.030(2) -0.0051(15) 0.0013(15) -0.0042(15) C13 0.0187(18) 0.032(2) 0.030(2) -0.0047(16) 0.0030(15) -0.0034(15) C14 0.0244(18) 0.0237(18) 0.0268(19) -0.0063(15) 0.0026(15) -0.0024(14) C15 0.0180(17) 0.0264(18) 0.0232(18) -0.0036(14) 0.0011(14) -0.0022(14) C16 0.0224(18) 0.0259(19) 0.0281(19) -0.0036(15) 0.0014(15) -0.0065(15) C17 0.0269(19) 0.037(2) 0.026(2) -0.0050(16) -0.0018(15) -0.0054(16) C18 0.0220(19) 0.053(2) 0.030(2) 0.0020(18) -0.0052(16) -0.0130(18) C19 0.0248(19) 0.042(2) 0.033(2) 0.0004(17) -0.0056(16) -0.0126(17) C20 0.035(3) 0.072(4) 0.042(3) 0.012(3) -0.005(2) -0.027(3) C21 0.033(2) 0.038(3) 0.053(3) -0.012(2) -0.007(2) -0.008(2) C22 0.032(2) 0.0225(18) 0.0250(18) -0.0008(14) -0.0026(15) -0.0041(15) C23 0.0270(19) 0.022(2) 0.033(2) -0.0079(16) 0.0000(15) -0.0010(16) C24 0.0276(19) 0.0252(19) 0.0210(18) -0.0003(14) 0.0004(15) -0.0002(15) C25 0.0251(18) 0.0254(18) 0.0166(17) 0.0008(14) -0.0001(14) -0.0029(15) C26 0.0253(18) 0.0257(19) 0.0206(18) -0.0015(14) 0.0007(14) -0.0048(15) C27 0.0264(19) 0.033(2) 0.0214(18) -0.0003(15) -0.0017(15) -0.0056(16) C28 0.033(2) 0.0240(19) 0.030(2) -0.0048(15) 0.0002(16) -0.0093(16) C29 0.033(2) 0.0255(19) 0.0245(19) -0.0029(15) 0.0035(15) -0.0054(16) C30 0.040(2) 0.028(2) 0.037(3) -0.0065(18) 0.006(2) -0.0030(19) C31 0.179(7) 0.072(4) 0.037(3) -0.010(3) -0.004(3) -0.011(4) Li1' 0.031(3) 0.056(4) 0.030(3) 0.009(3) -0.002(3) -0.004(3) Li2' 0.027(3) 0.038(3) 0.031(3) 0.003(3) -0.001(3) 0.000(3) O1' 0.0267(13) 0.0480(15) 0.0233(13) 0.0049(11) -0.0017(10) -0.0073(11) O2' 0.0295(14) 0.081(2) 0.0276(15) 0.0112(14) 0.0023(11) -0.0117(14) O3' 0.0209(12) 0.0309(13) 0.0215(12) -0.0019(10) -0.0014(10) -0.0062(10) O4' 0.0222(12) 0.0303(13) 0.0250(13) -0.0005(10) -0.0008(10) -0.0060(10) O5' 0.0299(13) 0.0420(15) 0.0236(13) 0.0021(11) 0.0011(10) -0.0065(11) O6' 0.0263(14) 0.0636(18) 0.0259(14) 0.0059(13) -0.0018(11) -0.0009(13) O7' 0.0224(12) 0.0268(13) 0.0260(12) 0.0035(10) -0.0032(10) -0.0046(10) O8' 0.0240(13) 0.0422(15) 0.0299(14) 0.0053(11) -0.0012(11) -0.0122(11) O9' 0.0261(14) 0.0351(14) 0.0435(15) -0.0073(12) -0.0011(11) -0.0068(11) O10' 0.0233(13) 0.0318(14) 0.0367(14) -0.0055(11) 0.0007(11) 0.0009(11) O11' 0.0277(13) 0.0265(13) 0.0412(15) -0.0090(11) 0.0056(11) -0.0018(11) O12' 0.0263(13) 0.0282(13) 0.0381(14) -0.0064(11) 0.0000(11) -0.0060(11) O13' 0.080(2) 0.066(2) 0.0359(17) -0.0113(15) 0.0046(15) -0.0111(17) C1' 0.028(2) 0.039(2) 0.030(2) 0.0010(19) 0.0027(18) -0.0070(18) C2' 0.0256(18) 0.0254(19) 0.031(2) -0.0058(15) -0.0022(15) -0.0056(15) C3' 0.0237(19) 0.033(2) 0.031(2) -0.0031(16) -0.0015(16) -0.0058(16) C4' 0.0285(19) 0.0289(19) 0.0239(19) -0.0028(15) 0.0006(15) -0.0040(15) C5' 0.0240(18) 0.0294(19) 0.0249(19) 0.0002(15) -0.0002(14) -0.0041(15) C6' 0.0224(18) 0.0236(18) 0.0256(19) -0.0045(15) 0.0001(15) -0.0022(14) C7' 0.0263(19) 0.040(2) 0.026(2) 0.0004(16) 0.0009(15) -0.0027(16) C8' 0.0230(19) 0.041(2) 0.033(2) -0.0018(17) 0.0041(16) -0.0091(17) C9' 0.0260(19) 0.0254(19) 0.031(2) -0.0047(15) 0.0012(15) -0.0043(15) C10' 0.026(2) 0.042(3) 0.030(2) 0.0013(18) -0.0036(17) -0.0138(19) C11' 0.026(2) 0.051(3) 0.035(2) -0.002(2) -0.0031(18) -0.012(2) C12' 0.0175(17) 0.0284(19) 0.032(2) -0.0060(15) 0.0021(15) -0.0050(14) C13' 0.0180(18) 0.031(2) 0.030(2) -0.0057(16) 0.0006(15) -0.0016(15) C14' 0.0270(19) 0.0263(19) 0.0237(19) -0.0045(15) 0.0046(15) -0.0025(15) C15' 0.0202(17) 0.0282(19) 0.0237(18) -0.0028(15) 0.0018(14) -0.0014(14) C16' 0.0176(17) 0.0276(19) 0.0264(18) -0.0032(15) -0.0028(14) -0.0035(14) C17' 0.0245(19) 0.038(2) 0.030(2) -0.0035(17) -0.0019(16) 0.0035(16) C18' 0.0199(19) 0.057(3) 0.028(2) -0.0003(18) -0.0029(16) -0.0084(18) C19' 0.0237(19) 0.050(2) 0.032(2) -0.0031(18) 0.0000(16) -0.0109(17) C20' 0.029(2) 0.078(4) 0.034(3) 0.008(3) -0.0039(19) -0.025(2) C21' 0.036(2) 0.029(2) 0.049(3) -0.007(2) 0.009(2) -0.0009(19) C22' 0.035(2) 0.029(2) 0.029(2) -0.0061(16) 0.0046(16) -0.0072(17) C23' 0.038(2) 0.026(2) 0.028(2) -0.0046(15) -0.0008(16) -0.0085(17) C24' 0.033(2) 0.029(2) 0.0216(18) 0.0012(15) -0.0047(15) -0.0083(16) C25' 0.0288(19) 0.0229(18) 0.0203(17) -0.0013(14) -0.0014(14) -0.0035(15) C26' 0.031(2) 0.027(2) 0.0237(18) -0.0022(15) -0.0004(15) -0.0044(16) C27' 0.031(2) 0.0300(19) 0.0185(18) -0.0015(14) 0.0003(15) -0.0027(16) C28' 0.035(2) 0.023(2) 0.030(2) -0.0063(16) 0.0010(16) -0.0035(17) C29' 0.032(2) 0.0262(19) 0.0245(19) -0.0018(15) -0.0036(15) -0.0069(16) C30' 0.038(2) 0.042(3) 0.052(3) -0.014(2) -0.003(2) -0.016(2) C31' 0.158(6) 0.108(5) 0.063(4) -0.037(4) 0.015(4) -0.029(4) Cl1 0.0273(5) 0.0349(5) 0.0290(5) -0.0041(4) -0.0004(4) 0.0004(4) Cl2 0.0249(5) 0.0371(5) 0.0401(5) -0.0004(4) -0.0014(4) -0.0081(4) Cl3 0.0256(4) 0.0327(5) 0.0268(5) -0.0040(4) 0.0001(4) -0.0014(4) Cl4 0.0265(5) 0.0346(5) 0.0292(5) -0.0040(4) 0.0004(4) -0.0080(4) O14 0.0429(16) 0.0586(18) 0.0289(14) 0.0038(12) -0.0008(12) -0.0141(14) O15 0.107(3) 0.0364(17) 0.0371(17) -0.0029(13) 0.0048(16) 0.0105(16) O16 0.0269(14) 0.073(2) 0.0529(18) -0.0238(15) 0.0051(13) -0.0001(14) O17 0.0414(17) 0.075(2) 0.071(2) -0.0255(17) -0.0076(15) -0.0187(15) O18 0.052(2) 0.205(5) 0.076(3) 0.084(3) -0.0125(19) -0.021(3) O19 0.056(2) 0.071(2) 0.121(3) -0.053(2) 0.000(2) 0.0078(17) O20 0.0322(16) 0.0470(18) 0.151(3) -0.035(2) -0.0161(18) -0.0115(14) O21 0.0225(13) 0.0500(16) 0.0476(16) 0.0004(13) -0.0052(11) -0.0070(12) O22 0.079(2) 0.0333(15) 0.0367(16) -0.0014(12) 0.0065(14) 0.0075(14) O23 0.0239(14) 0.0716(19) 0.0440(16) -0.0174(14) 0.0029(12) -0.0029(13) O24 0.0396(16) 0.0635(19) 0.0646(19) -0.0248(16) 0.0011(14) -0.0229(14) O25 0.0462(16) 0.0545(17) 0.0281(14) -0.0008(12) 0.0014(12) -0.0073(14) O26 0.0515(19) 0.108(3) 0.0389(17) 0.0280(17) -0.0004(14) -0.0048(18) O27 0.0385(17) 0.0526(19) 0.150(3) -0.049(2) -0.0055(19) -0.0138(15) O28 0.0615(19) 0.0585(19) 0.0443(17) -0.0235(15) 0.0006(14) 0.0084(15) O29 0.0244(13) 0.0518(17) 0.0456(16) 0.0041(13) -0.0046(12) -0.0034(12) O1S 0.088(3) 0.078(2) 0.086(3) -0.014(2) -0.017(2) -0.005(2) C1S 0.092(5) 0.113(5) 0.133(6) -0.081(4) -0.041(4) 0.041(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 Li1 O13 1.957(7) . ? Li1 O2 1.975(6) . ? Li1 O6 1.997(6) . ? Li1 O5 2.105(6) . ? Li1 O1 2.127(6) . ? Li1 Li2 2.944(8) . ? Li2 O9 1.889(6) . ? Li2 O10 1.916(6) . ? Li2 O1 1.923(6) . ? Li2 O5 1.940(6) . ? O1 C4 1.255(4) . ? O2 C7 1.237(4) . ? O3 C6 1.330(4) . ? O3 C2 1.377(4) . ? O4 C6 1.328(4) . ? O4 C9 1.386(4) . ? O5 C14 1.243(4) . ? O6 C17 1.230(4) . ? O7 C16 1.335(4) . ? O7 C12 1.390(4) . ? O8 C16 1.329(4) . ? O8 C19 1.389(4) . ? O9 C24 1.252(4) . ? O10 C27 1.246(4) . ? O11 C26 1.326(4) . ? O11 C22 1.388(4) . ? O12 C26 1.328(4) . ? O12 C29 1.385(4) . ? O13 C31 1.386(5) . ? O13 H13A 0.9500 . ? C1 C2 1.478(5) . ? C1 H1A 0.94(4) . ? C1 H1B 0.97(3) . ? C1 H1C 0.95(4) . ? C2 C3 1.341(5) . ? C3 C4 1.429(5) . ? C3 H3 0.82(3) . ? C4 C5 1.448(4) . ? C5 C6 1.358(4) . ? C5 C7 1.456(5) . ? C7 C8 1.449(5) . ? C8 C9 1.320(5) . ? C8 H8 0.82(4) . ? C9 C10 1.484(5) . ? C10 H10A 0.85(4) . ? C10 H10B 1.02(3) . ? C10 H10C 1.02(4) . ? C11 C12 1.482(5) . ? C11 H11A 0.99(3) . ? C11 H11B 0.96(3) . ? C11 H11C 0.93(4) . ? C12 C13 1.327(4) . ? C13 C14 1.447(4) . ? C13 H13 0.93(3) . ? C14 C15 1.446(4) . ? C15 C16 1.353(4) . ? C15 C17 1.463(4) . ? C17 C18 1.447(5) . ? C18 C19 1.332(5) . ? C18 H18 0.92(4) . ? C19 C20 1.487(5) . ? C20 H20A 0.90(4) . ? C20 H20B 0.94(5) . ? C20 H20C 0.94(4) . ? C21 C22 1.471(5) . ? C21 H21A 0.81(4) . ? C21 H21B 0.94(4) . ? C21 H21C 0.99(3) . ? C22 C23 1.326(4) . ? C23 C24 1.430(5) . ? C23 H23 0.86(3) . ? C24 C25 1.451(4) . ? C25 C26 1.357(4) . ? C25 C27 1.460(4) . ? C27 C28 1.437(5) . ? C28 C29 1.324(5) . ? C28 H28 0.93(3) . ? C29 C30 1.479(5) . ? C30 H30A 0.96(4) . ? C30 H30B 0.90(4) . ? C30 H30C 0.90(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? Li1' O13' 1.966(7) . ? Li1' O2' 1.974(6) . ? Li1' O6' 1.987(6) . ? Li1' O1' 2.085(6) . ? Li1' O5' 2.142(7) . ? Li1' Li2' 2.923(8) . ? Li2' O9' 1.906(6) . ? Li2' O10' 1.911(6) . ? Li2' O5' 1.935(6) . ? Li2' O1' 1.935(6) . ? O1' C4' 1.252(4) . ? O2' C7' 1.233(4) . ? O3' C6' 1.329(4) . ? O3' C2' 1.380(4) . ? O4' C6' 1.337(4) . ? O4' C9' 1.383(4) . ? O5' C14' 1.246(4) . ? O6' C17' 1.232(4) . ? O7' C16' 1.340(4) . ? O7' C12' 1.387(4) . ? O8' C16' 1.326(4) . ? O8' C19' 1.389(4) . ? O9' C24' 1.250(4) . ? O10' C27' 1.250(4) . ? O11' C26' 1.327(4) . ? O11' C22' 1.383(4) . ? O12' C26' 1.325(4) . ? O12' C29' 1.380(4) . ? O13' C31' 1.406(5) . ? O13' H13B 0.9500 . ? C1' C2' 1.486(5) . ? C1' H1D 0.92(4) . ? C1' H1E 1.02(4) . ? C1' H1F 1.01(4) . ? C2' C3' 1.338(5) . ? C3' C4' 1.434(5) . ? C3' H3' 0.99(3) . ? C4' C5' 1.452(4) . ? C5' C6' 1.360(4) . ? C5' C7' 1.462(5) . ? C7' C8' 1.446(5) . ? C8' C9' 1.336(5) . ? C8' H8' 0.92(3) . ? C9' C10' 1.483(5) . ? C10' H10D 1.00(4) . ? C10' H10E 0.86(3) . ? C10' H10F 1.03(3) . ? C11' C12' 1.482(5) . ? C11' H11D 0.87(4) . ? C11' H11E 0.94(5) . ? C11' H11F 0.93(4) . ? C12' C13' 1.336(4) . ? C13' C14' 1.439(4) . ? C13' H13' 0.95(3) . ? C14' C15' 1.456(4) . ? C15' C16' 1.356(4) . ? C15' C17' 1.469(4) . ? C17' C18' 1.442(5) . ? C18' C19' 1.333(5) . ? C18' H18' 0.96(3) . ? C19' C20' 1.483(5) . ? C20' H20D 0.89(4) . ? C20' H20E 0.99(4) . ? C20' H20F 0.95(5) . ? C21' C22' 1.483(5) . ? C21' H21D 0.88(3) . ? C21' H21E 1.00(4) . ? C21' H21F 0.97(4) . ? C22' C23' 1.317(5) . ? C23' C24' 1.447(5) . ? C23' H23' 1.00(4) . ? C24' C25' 1.450(4) . ? C25' C26' 1.357(4) . ? C25' C27' 1.462(4) . ? C27' C28' 1.433(5) . ? C28' C29' 1.323(5) . ? C28' H28' 0.84(3) . ? C29' C30' 1.479(5) . ? C30' H30D 1.04(5) . ? C30' H30E 0.95(6) . ? C30' H30F 0.92(4) . ? C31' H31D 0.9800 . ? C31' H31E 0.9800 . ? C31' H31F 0.9800 . ? Cl1 O15 1.405(3) . ? Cl1 O16 1.419(3) . ? Cl1 O14 1.442(2) . ? Cl1 O17 1.445(3) . ? Cl2 O18 1.395(3) . ? Cl2 O20 1.408(3) . ? Cl2 O19 1.429(3) . ? Cl2 O21 1.434(2) . ? Cl3 O22 1.419(3) . ? Cl3 O23 1.433(2) . ? Cl3 O25 1.433(2) . ? Cl3 O24 1.441(3) . ? Cl4 O27 1.408(3) . ? Cl4 O26 1.412(3) . ? Cl4 O28 1.428(3) . ? Cl4 O29 1.434(2) . ? O1S C1S 1.467(6) . ? 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 O13 Li1 O2 101.6(3) . . ? O13 Li1 O6 112.6(3) . . ? O2 Li1 O6 93.6(3) . . ? O13 Li1 O5 104.7(3) . . ? O2 Li1 O5 151.6(4) . . ? O6 Li1 O5 86.2(2) . . ? O13 Li1 O1 94.3(3) . . ? O2 Li1 O1 86.1(2) . . ? O6 Li1 O1 152.6(3) . . ? O5 Li1 O1 81.4(2) . . ? O13 Li1 Li2 98.1(3) . . ? O2 Li1 Li2 124.3(3) . . ? O6 Li1 Li2 125.1(3) . . ? O5 Li1 Li2 41.13(16) . . ? O1 Li1 Li2 40.70(16) . . ? O9 Li2 O10 96.0(3) . . ? O9 Li2 O1 125.8(3) . . ? O10 Li2 O1 111.0(3) . . ? O9 Li2 O5 122.1(3) . . ? O10 Li2 O5 111.3(3) . . ? O1 Li2 O5 91.2(3) . . ? O9 Li2 Li1 137.7(3) . . ? O10 Li2 Li1 126.2(3) . . ? O1 Li2 Li1 46.16(18) . . ? O5 Li2 Li1 45.54(17) . . ? C4 O1 Li2 139.6(3) . . ? C4 O1 Li1 126.9(3) . . ? Li2 O1 Li1 93.1(2) . . ? C7 O2 Li1 131.0(3) . . ? C6 O3 C2 118.4(2) . . ? C6 O4 C9 118.0(3) . . ? C14 O5 Li2 134.3(3) . . ? C14 O5 Li1 130.0(3) . . ? Li2 O5 Li1 93.3(2) . . ? C17 O6 Li1 132.7(3) . . ? C16 O7 C12 117.7(2) . . ? C16 O8 C19 117.9(3) . . ? C24 O9 Li2 126.8(3) . . ? C27 O10 Li2 125.7(3) . . ? C26 O11 C22 117.6(2) . . ? C26 O12 C29 118.3(2) . . ? C31 O13 Li1 130.1(3) . . ? C31 O13 H13A 114.9 . . ? Li1 O13 H13A 114.9 . . ? C2 C1 H1A 106(2) . . ? C2 C1 H1B 111.0(18) . . ? H1A C1 H1B 111(3) . . ? C2 C1 H1C 118(2) . . ? H1A C1 H1C 101(3) . . ? H1B C1 H1C 110(3) . . ? C3 C2 O3 120.7(3) . . ? C3 C2 C1 128.1(3) . . ? O3 C2 C1 111.2(3) . . ? C2 C3 C4 122.3(3) . . ? C2 C3 H3 115(2) . . ? C4 C3 H3 122(2) . . ? O1 C4 C3 122.3(3) . . ? O1 C4 C5 122.2(3) . . ? C3 C4 C5 115.5(3) . . ? C6 C5 C4 117.6(3) . . ? C6 C5 C7 117.8(3) . . ? C4 C5 C7 124.6(3) . . ? O4 C6 O3 108.7(3) . . ? O4 C6 C5 125.8(3) . . ? O3 C6 C5 125.5(3) . . ? O2 C7 C8 122.2(3) . . ? O2 C7 C5 123.6(3) . . ? C8 C7 C5 114.2(3) . . ? C9 C8 C7 123.1(3) . . ? C9 C8 H8 115(3) . . ? C7 C8 H8 122(3) . . ? C8 C9 O4 120.9(3) . . ? C8 C9 C10 127.8(3) . . ? O4 C9 C10 111.3(3) . . ? C9 C10 H10A 109(3) . . ? C9 C10 H10B 108.5(18) . . ? H10A C10 H10B 110(3) . . ? C9 C10 H10C 110(2) . . ? H10A C10 H10C 109(3) . . ? H10B C10 H10C 109(3) . . ? C12 C11 H11A 110.3(17) . . ? C12 C11 H11B 114(2) . . ? H11A C11 H11B 104(3) . . ? C12 C11 H11C 112(2) . . ? H11A C11 H11C 109(3) . . ? H11B C11 H11C 107(3) . . ? C13 C12 O7 120.8(3) . . ? C13 C12 C11 128.9(3) . . ? O7 C12 C11 110.3(3) . . ? C12 C13 C14 122.5(3) . . ? C12 C13 H13 116(2) . . ? C14 C13 H13 122(2) . . ? O5 C14 C15 122.7(3) . . ? O5 C14 C13 122.5(3) . . ? C15 C14 C13 114.8(3) . . ? C16 C15 C14 118.1(3) . . ? C16 C15 C17 117.6(3) . . ? C14 C15 C17 124.2(3) . . ? O8 C16 O7 108.1(3) . . ? O8 C16 C15 126.4(3) . . ? O7 C16 C15 125.6(3) . . ? O6 C17 C18 122.0(3) . . ? O6 C17 C15 123.6(3) . . ? C18 C17 C15 114.4(3) . . ? C19 C18 C17 123.0(3) . . ? C19 C18 H18 118(2) . . ? C17 C18 H18 119(2) . . ? C18 C19 O8 120.6(3) . . ? C18 C19 C20 128.6(3) . . ? O8 C19 C20 110.8(3) . . ? C19 C20 H20A 109(3) . . ? C19 C20 H20B 108(3) . . ? H20A C20 H20B 109(4) . . ? C19 C20 H20C 112(2) . . ? H20A C20 H20C 105(4) . . ? H20B C20 H20C 114(4) . . ? C22 C21 H21A 113(3) . . ? C22 C21 H21B 114(2) . . ? H21A C21 H21B 104(4) . . ? C22 C21 H21C 108.8(19) . . ? H21A C21 H21C 112(4) . . ? H21B C21 H21C 105(3) . . ? C23 C22 O11 120.8(3) . . ? C23 C22 C21 129.3(3) . . ? O11 C22 C21 109.9(3) . . ? C22 C23 C24 122.9(3) . . ? C22 C23 H23 112(2) . . ? C24 C23 H23 125(2) . . ? O9 C24 C23 122.1(3) . . ? O9 C24 C25 122.8(3) . . ? C23 C24 C25 115.1(3) . . ? C26 C25 C24 117.3(3) . . ? C26 C25 C27 117.5(3) . . ? C24 C25 C27 125.1(3) . . ? O11 C26 O12 108.1(3) . . ? O11 C26 C25 126.2(3) . . ? O12 C26 C25 125.7(3) . . ? O10 C27 C28 122.2(3) . . ? O10 C27 C25 123.2(3) . . ? C28 C27 C25 114.6(3) . . ? C29 C28 C27 123.3(3) . . ? C29 C28 H28 116.6(19) . . ? C27 C28 H28 120.0(19) . . ? C28 C29 O12 120.4(3) . . ? C28 C29 C30 129.4(3) . . ? O12 C29 C30 110.2(3) . . ? C29 C30 H30A 109(2) . . ? C29 C30 H30B 109(3) . . ? H30A C30 H30B 113(4) . . ? C29 C30 H30C 109(2) . . ? H30A C30 H30C 107(3) . . ? H30B C30 H30C 109(4) . . ? O13 C31 H31A 109.5 . . ? O13 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O13 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O13' Li1' O2' 106.2(3) . . ? O13' Li1' O6' 101.1(3) . . ? O2' Li1' O6' 97.8(3) . . ? O13' Li1' O1' 101.8(3) . . ? O2' Li1' O1' 87.4(2) . . ? O6' Li1' O1' 154.1(4) . . ? O13' Li1' O5' 92.8(3) . . ? O2' Li1' O5' 159.3(4) . . ? O6' Li1' O5' 86.0(2) . . ? O1' Li1' O5' 80.9(2) . . ? O13' Li1' Li2' 89.9(3) . . ? O2' Li1' Li2' 128.7(3) . . ? O6' Li1' Li2' 127.0(3) . . ? O1' Li1' Li2' 41.38(17) . . ? O5' Li1' Li2' 41.43(17) . . ? O9' Li2' O10' 95.9(3) . . ? O9' Li2' O5' 113.6(3) . . ? O10' Li2' O5' 121.0(3) . . ? O9' Li2' O1' 113.3(3) . . ? O10' Li2' O1' 124.2(3) . . ? O5' Li2' O1' 90.2(3) . . ? O9' Li2' Li1' 112.7(3) . . ? O10' Li2' Li1' 151.4(3) . . ? O5' Li2' Li1' 47.09(19) . . ? O1' Li2' Li1' 45.42(18) . . ? C4' O1' Li2' 136.6(3) . . ? C4' O1' Li1' 129.2(3) . . ? Li2' O1' Li1' 93.2(3) . . ? C7' O2' Li1' 131.6(3) . . ? C6' O3' C2' 117.9(2) . . ? C6' O4' C9' 118.1(3) . . ? C14' O5' Li2' 137.7(3) . . ? C14' O5' Li1' 125.3(3) . . ? Li2' O5' Li1' 91.5(3) . . ? C17' O6' Li1' 127.4(3) . . ? C16' O7' C12' 117.8(2) . . ? C16' O8' C19' 117.9(3) . . ? C24' O9' Li2' 126.1(3) . . ? C27' O10' Li2' 126.5(3) . . ? C26' O11' C22' 118.0(3) . . ? C26' O12' C29' 118.0(3) . . ? C31' O13' Li1' 122.5(4) . . ? C31' O13' H13B 118.7 . . ? Li1' O13' H13B 118.7 . . ? C2' C1' H1D 115(3) . . ? C2' C1' H1E 109(2) . . ? H1D C1' H1E 105(3) . . ? C2' C1' H1F 108(2) . . ? H1D C1' H1F 106(3) . . ? H1E C1' H1F 114(3) . . ? C3' C2' O3' 121.0(3) . . ? C3' C2' C1' 127.4(3) . . ? O3' C2' C1' 111.6(3) . . ? C2' C3' C4' 122.2(3) . . ? C2' C3' H3' 118.0(18) . . ? C4' C3' H3' 119.7(18) . . ? O1' C4' C3' 122.6(3) . . ? O1' C4' C5' 121.9(3) . . ? C3' C4' C5' 115.6(3) . . ? C6' C5' C4' 117.2(3) . . ? C6' C5' C7' 117.7(3) . . ? C4' C5' C7' 125.1(3) . . ? O3' C6' O4' 108.2(3) . . ? O3' C6' C5' 126.1(3) . . ? O4' C6' C5' 125.7(3) . . ? O2' C7' C8' 122.0(3) . . ? O2' C7' C5' 123.1(3) . . ? C8' C7' C5' 114.9(3) . . ? C9' C8' C7' 122.4(3) . . ? C9' C8' H8' 118(2) . . ? C7' C8' H8' 120(2) . . ? C8' C9' O4' 121.2(3) . . ? C8' C9' C10' 127.8(3) . . ? O4' C9' C10' 111.0(3) . . ? C9' C10' H10D 113(2) . . ? C9' C10' H10E 112(2) . . ? H10D C10' H10E 109(3) . . ? C9' C10' H10F 111.5(18) . . ? H10D C10' H10F 103(3) . . ? H10E C10' H10F 107(3) . . ? C12' C11' H11D 113(3) . . ? C12' C11' H11E 112(3) . . ? H11D C11' H11E 110(4) . . ? C12' C11' H11F 109(3) . . ? H11D C11' H11F 107(4) . . ? H11E C11' H11F 105(4) . . ? C13' C12' O7' 121.0(3) . . ? C13' C12' C11' 128.7(3) . . ? O7' C12' C11' 110.3(3) . . ? C12' C13' C14' 122.3(3) . . ? C12' C13' H13' 113(2) . . ? C14' C13' H13' 125(2) . . ? O5' C14' C13' 122.5(3) . . ? O5' C14' C15' 122.2(3) . . ? C13' C14' C15' 115.3(3) . . ? C16' C15' C14' 117.7(3) . . ? C16' C15' C17' 117.5(3) . . ? C14' C15' C17' 124.7(3) . . ? O8' C16' O7' 108.0(3) . . ? O8' C16' C15' 126.4(3) . . ? O7' C16' C15' 125.6(3) . . ? O6' C17' C18' 122.5(3) . . ? O6' C17' C15' 123.3(3) . . ? C18' C17' C15' 114.2(3) . . ? C19' C18' C17' 123.2(3) . . ? C19' C18' H18' 119(2) . . ? C17' C18' H18' 118(2) . . ? C18' C19' O8' 120.7(3) . . ? C18' C19' C20' 128.5(3) . . ? O8' C19' C20' 110.8(3) . . ? C19' C20' H20D 109(3) . . ? C19' C20' H20E 114(2) . . ? H20D C20' H20E 109(4) . . ? C19' C20' H20F 110(3) . . ? H20D C20' H20F 114(4) . . ? H20E C20' H20F 101(3) . . ? C22' C21' H21D 113(2) . . ? C22' C21' H21E 112(2) . . ? H21D C21' H21E 111(3) . . ? C22' C21' H21F 113(2) . . ? H21D C21' H21F 99(3) . . ? H21E C21' H21F 107(3) . . ? C23' C22' O11' 121.5(3) . . ? C23' C22' C21' 128.2(4) . . ? O11' C22' C21' 110.3(3) . . ? C22' C23' C24' 122.3(3) . . ? C22' C23' H23' 123(2) . . ? C24' C23' H23' 115(2) . . ? O9' C24' C23' 121.5(3) . . ? O9' C24' C25' 123.7(3) . . ? C23' C24' C25' 114.8(3) . . ? C26' C25' C24' 117.9(3) . . ? C26' C25' C27' 117.1(3) . . ? C24' C25' C27' 125.0(3) . . ? O12' C26' O11' 108.3(3) . . ? O12' C26' C25' 126.2(3) . . ? O11' C26' C25' 125.5(3) . . ? O10' C27' C28' 122.5(3) . . ? O10' C27' C25' 122.8(3) . . ? C28' C27' C25' 114.7(3) . . ? C29' C28' C27' 123.2(3) . . ? C29' C28' H28' 119(2) . . ? C27' C28' H28' 118(2) . . ? C28' C29' O12' 120.8(3) . . ? C28' C29' C30' 129.4(3) . . ? O12' C29' C30' 109.8(3) . . ? C29' C30' H30D 113(3) . . ? C29' C30' H30E 115(3) . . ? H30D C30' H30E 95(4) . . ? C29' C30' H30F 110(2) . . ? H30D C30' H30F 113(3) . . ? H30E C30' H30F 110(4) . . ? O13' C31' H31D 109.5 . . ? O13' C31' H31E 109.5 . . ? H31D C31' H31E 109.5 . . ? O13' C31' H31F 109.5 . . ? H31D C31' H31F 109.5 . . ? H31E C31' H31F 109.5 . . ? O15 Cl1 O16 111.38(19) . . ? O15 Cl1 O14 109.48(16) . . ? O16 Cl1 O14 110.17(16) . . ? O15 Cl1 O17 108.58(19) . . ? O16 Cl1 O17 107.95(17) . . ? O14 Cl1 O17 109.22(17) . . ? O18 Cl2 O20 111.4(3) . . ? O18 Cl2 O19 108.3(3) . . ? O20 Cl2 O19 107.5(2) . . ? O18 Cl2 O21 109.94(18) . . ? O20 Cl2 O21 110.43(16) . . ? O19 Cl2 O21 109.26(18) . . ? O22 Cl3 O23 110.48(17) . . ? O22 Cl3 O25 109.90(16) . . ? O23 Cl3 O25 110.47(15) . . ? O22 Cl3 O24 108.08(18) . . ? O23 Cl3 O24 108.75(16) . . ? O25 Cl3 O24 109.12(16) . . ? O27 Cl4 O26 111.1(2) . . ? O27 Cl4 O28 108.68(19) . . ? O26 Cl4 O28 107.65(19) . . ? O27 Cl4 O29 109.74(17) . . ? O26 Cl4 O29 109.71(16) . . ? O28 Cl4 O29 109.96(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O13 Li1 Li2 O9 11.5(5) . . . . ? O2 Li1 Li2 O9 121.6(5) . . . . ? O6 Li1 Li2 O9 -113.6(5) . . . . ? O5 Li1 Li2 O9 -91.5(5) . . . . ? O1 Li1 Li2 O9 98.5(5) . . . . ? O13 Li1 Li2 O10 -172.0(3) . . . . ? O2 Li1 Li2 O10 -61.9(5) . . . . ? O6 Li1 Li2 O10 62.9(5) . . . . ? O5 Li1 Li2 O10 85.0(4) . . . . ? O1 Li1 Li2 O10 -84.9(4) . . . . ? O13 Li1 Li2 O1 -87.1(3) . . . . ? O2 Li1 Li2 O1 23.0(3) . . . . ? O6 Li1 Li2 O1 147.9(4) . . . . ? O5 Li1 Li2 O1 169.9(4) . . . . ? O13 Li1 Li2 O5 103.0(3) . . . . ? O2 Li1 Li2 O5 -146.9(4) . . . . ? O6 Li1 Li2 O5 -22.1(3) . . . . ? O1 Li1 Li2 O5 -169.9(4) . . . . ? O9 Li2 O1 C4 48.3(6) . . . . ? O10 Li2 O1 C4 -66.2(5) . . . . ? O5 Li2 O1 C4 -179.6(4) . . . . ? Li1 Li2 O1 C4 173.2(5) . . . . ? O9 Li2 O1 Li1 -124.9(4) . . . . ? O10 Li2 O1 Li1 120.6(3) . . . . ? O5 Li2 O1 Li1 7.2(3) . . . . ? O13 Li1 O1 C4 -77.0(4) . . . . ? O2 Li1 O1 C4 24.4(4) . . . . ? O6 Li1 O1 C4 114.6(7) . . . . ? O5 Li1 O1 C4 178.8(3) . . . . ? Li2 Li1 O1 C4 -174.5(4) . . . . ? O13 Li1 O1 Li2 97.5(3) . . . . ? O2 Li1 O1 Li2 -161.1(3) . . . . ? O6 Li1 O1 Li2 -70.9(7) . . . . ? O5 Li1 O1 Li2 -6.7(3) . . . . ? O13 Li1 O2 C7 70.9(5) . . . . ? O6 Li1 O2 C7 -175.2(4) . . . . ? O5 Li1 O2 C7 -86.5(8) . . . . ? O1 Li1 O2 C7 -22.7(5) . . . . ? Li2 Li1 O2 C7 -37.5(6) . . . . ? O9 Li2 O5 C14 -69.6(5) . . . . ? O10 Li2 O5 C14 42.6(5) . . . . ? O1 Li2 O5 C14 155.7(3) . . . . ? Li1 Li2 O5 C14 162.9(4) . . . . ? O9 Li2 O5 Li1 127.5(4) . . . . ? O10 Li2 O5 Li1 -120.4(3) . . . . ? O1 Li2 O5 Li1 -7.3(3) . . . . ? O13 Li1 O5 C14 110.4(3) . . . . ? O2 Li1 O5 C14 -92.5(7) . . . . ? O6 Li1 O5 C14 -2.0(4) . . . . ? O1 Li1 O5 C14 -157.4(3) . . . . ? Li2 Li1 O5 C14 -164.1(4) . . . . ? O13 Li1 O5 Li2 -85.6(3) . . . . ? O2 Li1 O5 Li2 71.5(7) . . . . ? O6 Li1 O5 Li2 162.1(3) . . . . ? O1 Li1 O5 Li2 6.6(3) . . . . ? O13 Li1 O6 C17 -109.4(4) . . . . ? O2 Li1 O6 C17 146.4(3) . . . . ? O5 Li1 O6 C17 -5.1(5) . . . . ? O1 Li1 O6 C17 58.1(9) . . . . ? Li2 Li1 O6 C17 9.3(6) . . . . ? O10 Li2 O9 C24 5.1(4) . . . . ? O1 Li2 O9 C24 -116.1(4) . . . . ? O5 Li2 O9 C24 124.9(4) . . . . ? Li1 Li2 O9 C24 -177.7(3) . . . . ? O9 Li2 O10 C27 -5.9(4) . . . . ? O1 Li2 O10 C27 126.2(3) . . . . ? O5 Li2 O10 C27 -133.8(3) . . . . ? Li1 Li2 O10 C27 176.4(3) . . . . ? O2 Li1 O13 C31 146.1(5) . . . . ? O6 Li1 O13 C31 47.2(6) . . . . ? O5 Li1 O13 C31 -44.8(6) . . . . ? O1 Li1 O13 C31 -127.1(5) . . . . ? Li2 Li1 O13 C31 -86.3(5) . . . . ? C6 O3 C2 C3 1.0(4) . . . . ? C6 O3 C2 C1 -178.0(3) . . . . ? O3 C2 C3 C4 -3.2(5) . . . . ? C1 C2 C3 C4 175.7(4) . . . . ? Li2 O1 C4 C3 -10.1(6) . . . . ? Li1 O1 C4 C3 161.4(3) . . . . ? Li2 O1 C4 C5 170.5(4) . . . . ? Li1 O1 C4 C5 -18.0(5) . . . . ? C2 C3 C4 O1 -176.3(3) . . . . ? C2 C3 C4 C5 3.1(5) . . . . ? O1 C4 C5 C6 178.4(3) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? O1 C4 C5 C7 -0.2(6) . . . . ? C3 C4 C5 C7 -179.7(3) . . . . ? C9 O4 C6 O3 179.1(2) . . . . ? C9 O4 C6 C5 -1.0(5) . . . . ? C2 O3 C6 O4 -179.0(2) . . . . ? C2 O3 C6 C5 1.1(5) . . . . ? C4 C5 C6 O4 179.1(3) . . . . ? C7 C5 C6 O4 -2.2(5) . . . . ? C4 C5 C6 O3 -1.0(5) . . . . ? C7 C5 C6 O3 177.7(3) . . . . ? Li1 O2 C7 C8 -165.2(4) . . . . ? Li1 O2 C7 C5 14.3(7) . . . . ? C6 C5 C7 O2 -175.3(4) . . . . ? C4 C5 C7 O2 3.3(6) . . . . ? C6 C5 C7 C8 4.3(5) . . . . ? C4 C5 C7 C8 -177.1(3) . . . . ? O2 C7 C8 C9 175.9(4) . . . . ? C5 C7 C8 C9 -3.6(6) . . . . ? C7 C8 C9 O4 0.6(6) . . . . ? C7 C8 C9 C10 -177.8(4) . . . . ? C6 O4 C9 C8 1.9(5) . . . . ? C6 O4 C9 C10 -179.5(3) . . . . ? C16 O7 C12 C13 -8.3(4) . . . . ? C16 O7 C12 C11 170.9(3) . . . . ? O7 C12 C13 C14 3.6(5) . . . . ? C11 C12 C13 C14 -175.4(3) . . . . ? Li2 O5 C14 C15 -149.8(3) . . . . ? Li1 O5 C14 C15 7.7(5) . . . . ? Li2 O5 C14 C13 29.8(5) . . . . ? Li1 O5 C14 C13 -172.7(3) . . . . ? C12 C13 C14 O5 -177.1(3) . . . . ? C12 C13 C14 C15 2.6(5) . . . . ? O5 C14 C15 C16 175.6(3) . . . . ? C13 C14 C15 C16 -4.1(4) . . . . ? O5 C14 C15 C17 -7.9(5) . . . . ? C13 C14 C15 C17 172.4(3) . . . . ? C19 O8 C16 O7 177.4(3) . . . . ? C19 O8 C16 C15 -3.6(5) . . . . ? C12 O7 C16 O8 -174.1(2) . . . . ? C12 O7 C16 C15 6.9(5) . . . . ? C14 C15 C16 O8 -179.4(3) . . . . ? C17 C15 C16 O8 3.8(5) . . . . ? C14 C15 C16 O7 -0.7(5) . . . . ? C17 C15 C16 O7 -177.4(3) . . . . ? Li1 O6 C17 C18 -174.8(4) . . . . ? Li1 O6 C17 C15 5.9(6) . . . . ? C16 C15 C17 O6 177.6(3) . . . . ? C14 C15 C17 O6 1.1(5) . . . . ? C16 C15 C17 C18 -1.7(5) . . . . ? C14 C15 C17 C18 -178.3(3) . . . . ? O6 C17 C18 C19 -179.5(4) . . . . ? C15 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 O8 0.4(6) . . . . ? C17 C18 C19 C20 -179.9(5) . . . . ? C16 O8 C19 C18 1.4(5) . . . . ? C16 O8 C19 C20 -178.4(4) . . . . ? C26 O11 C22 C23 -1.4(4) . . . . ? C26 O11 C22 C21 178.6(3) . . . . ? O11 C22 C23 C24 0.0(5) . . . . ? C21 C22 C23 C24 -180.0(4) . . . . ? Li2 O9 C24 C23 178.5(3) . . . . ? Li2 O9 C24 C25 -1.2(5) . . . . ? C22 C23 C24 O9 -178.5(3) . . . . ? C22 C23 C24 C25 1.2(5) . . . . ? O9 C24 C25 C26 178.6(3) . . . . ? C23 C24 C25 C26 -1.1(4) . . . . ? O9 C24 C25 C27 -4.2(5) . . . . ? C23 C24 C25 C27 176.1(3) . . . . ? C22 O11 C26 O12 -178.3(2) . . . . ? C22 O11 C26 C25 1.5(4) . . . . ? C29 O12 C26 O11 175.7(2) . . . . ? C29 O12 C26 C25 -4.1(5) . . . . ? C24 C25 C26 O11 -0.2(5) . . . . ? C27 C25 C26 O11 -177.6(3) . . . . ? C24 C25 C26 O12 179.6(3) . . . . ? C27 C25 C26 O12 2.2(5) . . . . ? Li2 O10 C27 C28 -177.7(3) . . . . ? Li2 O10 C27 C25 2.8(5) . . . . ? C26 C25 C27 O10 -179.5(3) . . . . ? C24 C25 C27 O10 3.3(5) . . . . ? C26 C25 C27 C28 0.9(4) . . . . ? C24 C25 C27 C28 -176.3(3) . . . . ? O10 C27 C28 C29 178.4(3) . . . . ? C25 C27 C28 C29 -2.0(5) . . . . ? C27 C28 C29 O12 0.2(5) . . . . ? C27 C28 C29 C30 179.7(4) . . . . ? C26 O12 C29 C28 2.8(4) . . . . ? C26 O12 C29 C30 -176.8(3) . . . . ? O13' Li1' Li2' O9' -7.2(3) . . . . ? O2' Li1' Li2' O9' 103.6(4) . . . . ? O6' Li1' Li2' O9' -111.1(4) . . . . ? O1' Li1' Li2' O9' 100.9(3) . . . . ? O5' Li1' Li2' O9' -101.7(3) . . . . ? O13' Li1' Li2' O10' 170.9(6) . . . . ? O2' Li1' Li2' O10' -78.2(8) . . . . ? O6' Li1' Li2' O10' 67.0(8) . . . . ? O1' Li1' Li2' O10' -81.0(6) . . . . ? O5' Li1' Li2' O10' 76.5(6) . . . . ? O13' Li1' Li2' O5' 94.4(3) . . . . ? O2' Li1' Li2' O5' -154.7(5) . . . . ? O6' Li1' Li2' O5' -9.5(3) . . . . ? O1' Li1' Li2' O5' -157.4(4) . . . . ? O13' Li1' Li2' O1' -108.1(3) . . . . ? O2' Li1' Li2' O1' 2.7(4) . . . . ? O6' Li1' Li2' O1' 148.0(5) . . . . ? O5' Li1' Li2' O1' 157.4(4) . . . . ? O9' Li2' O1' C4' 68.7(5) . . . . ? O10' Li2' O1' C4' -46.6(6) . . . . ? O5' Li2' O1' C4' -175.4(3) . . . . ? Li1' Li2' O1' C4' 168.3(5) . . . . ? O9' Li2' O1' Li1' -99.6(3) . . . . ? O10' Li2' O1' Li1' 145.1(4) . . . . ? O5' Li2' O1' Li1' 16.3(3) . . . . ? O13' Li1' O1' C4' -93.5(4) . . . . ? O2' Li1' O1' C4' 12.5(5) . . . . ? O6' Li1' O1' C4' 114.9(7) . . . . ? O5' Li1' O1' C4' 175.5(3) . . . . ? Li2' Li1' O1' C4' -169.6(4) . . . . ? O13' Li1' O1' Li2' 76.1(3) . . . . ? O2' Li1' O1' Li2' -177.9(3) . . . . ? O6' Li1' O1' Li2' -75.4(8) . . . . ? O5' Li1' O1' Li2' -14.9(3) . . . . ? O13' Li1' O2' C7' 87.1(5) . . . . ? O6' Li1' O2' C7' -168.8(4) . . . . ? O1' Li1' O2' C7' -14.4(5) . . . . ? O5' Li1' O2' C7' -69.4(11) . . . . ? Li2' Li1' O2' C7' -16.2(7) . . . . ? O9' Li2' O5' C14' -52.6(6) . . . . ? O10' Li2' O5' C14' 60.5(6) . . . . ? O1' Li2' O5' C14' -168.3(3) . . . . ? Li1' Li2' O5' C14' -152.4(5) . . . . ? O9' Li2' O5' Li1' 99.8(3) . . . . ? O10' Li2' O5' Li1' -147.1(4) . . . . ? O1' Li2' O5' Li1' -15.9(3) . . . . ? O13' Li1' O5' C14' 71.0(4) . . . . ? O2' Li1' O5' C14' -131.5(9) . . . . ? O6' Li1' O5' C14' -30.0(4) . . . . ? O1' Li1' O5' C14' 172.4(3) . . . . ? Li2' Li1' O5' C14' 157.5(4) . . . . ? O13' Li1' O5' Li2' -86.6(3) . . . . ? O2' Li1' O5' Li2' 70.9(10) . . . . ? O6' Li1' O5' Li2' 172.4(3) . . . . ? O1' Li1' O5' Li2' 14.9(3) . . . . ? O13' Li1' O6' C17' -56.9(5) . . . . ? O2' Li1' O6' C17' -165.2(3) . . . . ? O1' Li1' O6' C17' 94.7(8) . . . . ? O5' Li1' O6' C17' 35.2(4) . . . . ? Li2' Li1' O6' C17' 41.5(6) . . . . ? O10' Li2' O9' C24' 0.2(4) . . . . ? O5' Li2' O9' C24' 127.8(3) . . . . ? O1' Li2' O9' C24' -131.1(3) . . . . ? Li1' Li2' O9' C24' 179.3(3) . . . . ? O9' Li2' O10' C27' -0.5(4) . . . . ? O5' Li2' O10' C27' -122.6(4) . . . . ? O1' Li2' O10' C27' 122.9(4) . . . . ? Li1' Li2' O10' C27' -178.8(5) . . . . ? O2' Li1' O13' C31' -47.6(5) . . . . ? O6' Li1' O13' C31' -149.2(4) . . . . ? O1' Li1' O13' C31' 43.1(5) . . . . ? O5' Li1' O13' C31' 124.3(4) . . . . ? Li2' Li1' O13' C31' 83.0(4) . . . . ? C6' O3' C2' C3' -2.2(4) . . . . ? C6' O3' C2' C1' 178.6(3) . . . . ? O3' C2' C3' C4' 2.6(5) . . . . ? C1' C2' C3' C4' -178.4(3) . . . . ? Li2' O1' C4' C3' 6.8(6) . . . . ? Li1' O1' C4' C3' 171.6(3) . . . . ? Li2' O1' C4' C5' -172.5(4) . . . . ? Li1' O1' C4' C5' -7.7(5) . . . . ? C2' C3' C4' O1' 178.8(3) . . . . ? C2' C3' C4' C5' -1.8(5) . . . . ? O1' C4' C5' C6' -180.0(3) . . . . ? C3' C4' C5' C6' 0.7(5) . . . . ? O1' C4' C5' C7' -1.3(5) . . . . ? C3' C4' C5' C7' 179.3(3) . . . . ? C2' O3' C6' O4' -179.1(2) . . . . ? C2' O3' C6' C5' 1.1(5) . . . . ? C9' O4' C6' O3' 178.5(2) . . . . ? C9' O4' C6' C5' -1.7(5) . . . . ? C4' C5' C6' O3' -0.4(5) . . . . ? C7' C5' C6' O3' -179.2(3) . . . . ? C4' C5' C6' O4' 179.8(3) . . . . ? C7' C5' C6' O4' 1.1(5) . . . . ? Li1' O2' C7' C8' -170.3(4) . . . . ? Li1' O2' C7' C5' 11.2(6) . . . . ? C6' C5' C7' O2' 178.6(3) . . . . ? C4' C5' C7' O2' 0.0(6) . . . . ? C6' C5' C7' C8' 0.0(5) . . . . ? C4' C5' C7' C8' -178.6(3) . . . . ? O2' C7' C8' C9' -179.1(4) . . . . ? C5' C7' C8' C9' -0.5(5) . . . . ? C7' C8' C9' O4' -0.1(5) . . . . ? C7' C8' C9' C10' 178.9(4) . . . . ? C6' O4' C9' C8' 1.1(5) . . . . ? C6' O4' C9' C10' -178.0(3) . . . . ? C16' O7' C12' C13' 6.6(4) . . . . ? C16' O7' C12' C11' -172.6(3) . . . . ? O7' C12' C13' C14' -1.6(5) . . . . ? C11' C12' C13' C14' 177.3(4) . . . . ? Li2' O5' C14' C13' -19.5(6) . . . . ? Li1' O5' C14' C13' -165.0(3) . . . . ? Li2' O5' C14' C15' 161.3(4) . . . . ? Li1' O5' C14' C15' 15.9(5) . . . . ? C12' C13' C14' O5' 176.9(3) . . . . ? C12' C13' C14' C15' -3.9(5) . . . . ? O5' C14' C15' C16' -176.3(3) . . . . ? C13' C14' C15' C16' 4.4(4) . . . . ? O5' C14' C15' C17' 7.1(5) . . . . ? C13' C14' C15' C17' -172.2(3) . . . . ? C19' O8' C16' O7' -177.4(3) . . . . ? C19' O8' C16' C15' 2.9(5) . . . . ? C12' O7' C16' O8' 174.3(2) . . . . ? C12' O7' C16' C15' -6.0(5) . . . . ? C14' C15' C16' O8' -180.0(3) . . . . ? C17' C15' C16' O8' -3.1(5) . . . . ? C14' C15' C16' O7' 0.4(5) . . . . ? C17' C15' C16' O7' 177.3(3) . . . . ? Li1' O6' C17' C18' 153.3(4) . . . . ? Li1' O6' C17' C15' -26.2(6) . . . . ? C16' C15' C17' O6' -179.6(3) . . . . ? C14' C15' C17' O6' -3.0(6) . . . . ? C16' C15' C17' C18' 0.8(5) . . . . ? C14' C15' C17' C18' 177.4(3) . . . . ? O6' C17' C18' C19' -178.1(4) . . . . ? C15' C17' C18' C19' 1.5(5) . . . . ? C17' C18' C19' O8' -1.8(6) . . . . ? C17' C18' C19' C20' 178.7(5) . . . . ? C16' O8' C19' C18' -0.3(5) . . . . ? C16' O8' C19' C20' 179.2(4) . . . . ? C26' O11' C22' C23' -1.2(5) . . . . ? C26' O11' C22' C21' 178.8(3) . . . . ? O11' C22' C23' C24' -1.0(5) . . . . ? C21' C22' C23' C24' 179.0(4) . . . . ? Li2' O9' C24' C23' -178.5(3) . . . . ? Li2' O9' C24' C25' 0.3(5) . . . . ? C22' C23' C24' O9' -178.7(3) . . . . ? C22' C23' C24' C25' 2.5(5) . . . . ? O9' C24' C25' C26' 179.3(3) . . . . ? C23' C24' C25' C26' -1.8(4) . . . . ? O9' C24' C25' C27' -0.7(5) . . . . ? C23' C24' C25' C27' 178.1(3) . . . . ? C29' O12' C26' O11' -179.9(3) . . . . ? C29' O12' C26' C25' 0.8(5) . . . . ? C22' O11' C26' O12' -177.4(3) . . . . ? C22' O11' C26' C25' 1.9(5) . . . . ? C24' C25' C26' O12' 178.8(3) . . . . ? C27' C25' C26' O12' -1.1(5) . . . . ? C24' C25' C26' O11' -0.3(5) . . . . ? C27' C25' C26' O11' 179.8(3) . . . . ? Li2' O10' C27' C28' 179.1(3) . . . . ? Li2' O10' C27' C25' 0.2(5) . . . . ? C26' C25' C27' O10' -179.6(3) . . . . ? C24' C25' C27' O10' 0.4(5) . . . . ? C26' C25' C27' C28' 1.4(4) . . . . ? C24' C25' C27' C28' -178.5(3) . . . . ? O10' C27' C28' C29' 179.3(3) . . . . ? C25' C27' C28' C29' -1.7(5) . . . . ? C27' C28' C29' O12' 1.5(5) . . . . ? C27' C28' C29' C30' -179.1(4) . . . . ? C26' O12' C29' C28' -1.0(4) . . . . ? C26' O12' C29' C30' 179.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13A O14 0.95 2.01 2.891(4) 153.1 1_554 O13' H13B O1S 0.95 1.92 2.780(4) 150.2 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.545 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.062 # Attachment '9a-jw41.cif' data_jw41 _database_code_depnum_ccdc_archive 'CCDC 774947' #TrackingRef '9a-jw41.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl2 Cu O18' _chemical_formula_weight 682.80 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9449(10) _cell_length_b 12.6414(13) _cell_length_c 10.4593(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.359(2) _cell_angle_gamma 90.00 _cell_volume 1309.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8778 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour light-blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 694 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7148 _exptl_absorpt_correction_T_max 0.8405 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14330 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2858 _reflns_number_gt 2707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0426P)^2^+0.4673P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2858 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.02471(9) Uani 1 2 d S . . Cl1 Cl 0.92585(4) 0.18584(3) 0.23069(3) 0.02848(10) Uani 1 1 d . . . O1 O 0.16446(10) 0.58265(9) 0.50432(10) 0.0316(2) Uani 1 1 d . . . O2 O 0.03631(11) 0.47309(9) 0.69818(11) 0.0314(2) Uani 1 1 d . . . O3 O 0.13870(11) 0.47540(9) 0.89226(11) 0.0299(2) Uani 1 1 d . . . O4 O 0.44999(10) 0.65681(8) 0.79470(10) 0.0286(2) Uani 1 1 d . . . O5 O 0.11682(15) 0.36234(11) 0.45820(13) 0.0424(3) Uani 1 1 d . . . O6 O 0.99628(13) 0.09097(10) 0.20393(14) 0.0493(3) Uani 1 1 d . . . O7 O 0.98452(13) 0.27586(9) 0.17356(12) 0.0425(3) Uani 1 1 d . . . O8 O 0.93096(13) 0.20162(10) 0.36829(11) 0.0428(3) Uani 1 1 d . . . O9 O 0.78483(12) 0.17753(10) 0.18373(13) 0.0432(3) Uani 1 1 d . . . C1 C 0.58625(16) 0.75273(14) 0.66217(18) 0.0354(3) Uani 1 1 d . . . C2 C 0.46071(15) 0.69016(11) 0.67169(16) 0.0286(3) Uani 1 1 d . . . C3 C 0.36647(15) 0.66601(12) 0.57551(16) 0.0304(3) Uani 1 1 d . . . C4 C 0.25004(14) 0.60354(11) 0.59663(14) 0.0271(3) Uani 1 1 d . . . C5 C 0.24295(13) 0.56942(11) 0.72764(14) 0.0249(3) Uani 1 1 d . . . C6 C 0.13444(15) 0.50487(11) 0.76640(16) 0.0267(3) Uani 1 1 d . . . C7 C 0.34366(13) 0.59793(11) 0.82094(14) 0.0256(3) Uani 1 1 d . . . C8 C 0.34245(15) 0.56621(12) 0.95034(15) 0.0284(3) Uani 1 1 d . . . C9 C 0.24078(16) 0.50474(11) 0.98236(16) 0.0291(3) Uani 1 1 d . . . C10 C 0.22412(19) 0.45957(16) 1.11022(17) 0.0396(4) Uani 1 1 d . . . H1A H 0.595(2) 0.8064(16) 0.730(2) 0.045(6) Uiso 1 1 d . . . H1B H 0.662(2) 0.7061(17) 0.676(2) 0.050(6) Uiso 1 1 d . . . H1C H 0.584(2) 0.7860(17) 0.583(2) 0.046(6) Uiso 1 1 d . . . H3 H 0.3744(19) 0.6873(15) 0.4958(19) 0.036(5) Uiso 1 1 d . . . H5A H 0.069(3) 0.316(2) 0.437(2) 0.056(7) Uiso 1 1 d . . . H5B H 0.167(3) 0.3473(19) 0.514(2) 0.054(7) Uiso 1 1 d . . . H8 H 0.410(2) 0.5862(15) 1.0066(19) 0.039(5) Uiso 1 1 d . . . H10A H 0.232(2) 0.385(2) 1.104(2) 0.058(6) Uiso 1 1 d . . . H10B H 0.137(3) 0.481(2) 1.134(3) 0.073(8) Uiso 1 1 d . . . H10C H 0.294(2) 0.4829(16) 1.171(2) 0.043(6) Uiso 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 Cu1 0.01980(13) 0.03124(15) 0.02237(14) -0.00117(9) -0.00190(9) -0.00231(9) Cl1 0.02645(18) 0.02583(18) 0.03277(19) 0.00009(13) 0.00076(14) -0.00139(12) O1 0.0248(5) 0.0402(6) 0.0293(5) -0.0022(4) 0.0005(4) -0.0057(4) O2 0.0217(5) 0.0365(5) 0.0353(6) -0.0013(5) -0.0007(4) -0.0063(4) O3 0.0223(5) 0.0334(5) 0.0337(6) 0.0012(4) 0.0009(4) -0.0043(4) O4 0.0212(5) 0.0288(5) 0.0354(6) -0.0019(4) 0.0013(4) -0.0046(4) O5 0.0412(7) 0.0440(7) 0.0392(7) -0.0026(6) -0.0119(6) -0.0025(6) O6 0.0443(7) 0.0321(6) 0.0736(9) -0.0035(6) 0.0175(7) 0.0058(5) O7 0.0478(7) 0.0326(6) 0.0494(7) 0.0005(5) 0.0169(6) -0.0082(5) O8 0.0438(7) 0.0525(7) 0.0312(6) 0.0041(5) -0.0017(5) 0.0032(6) O9 0.0328(6) 0.0420(7) 0.0520(8) -0.0028(5) -0.0107(5) -0.0039(5) C1 0.0258(7) 0.0382(8) 0.0424(9) 0.0002(7) 0.0044(6) -0.0078(6) C2 0.0231(7) 0.0259(7) 0.0373(8) -0.0008(6) 0.0048(6) 0.0001(5) C3 0.0248(7) 0.0331(7) 0.0337(8) -0.0006(6) 0.0054(6) -0.0017(6) C4 0.0218(6) 0.0266(7) 0.0329(7) -0.0034(6) 0.0029(5) 0.0010(5) C5 0.0197(6) 0.0237(6) 0.0313(7) -0.0023(5) 0.0020(5) 0.0012(5) C6 0.0221(7) 0.0256(7) 0.0321(7) -0.0020(5) 0.0021(6) 0.0015(5) C7 0.0193(6) 0.0231(6) 0.0344(7) -0.0032(5) 0.0022(5) 0.0011(5) C8 0.0221(6) 0.0293(7) 0.0328(7) -0.0025(6) -0.0023(5) 0.0000(5) C9 0.0244(7) 0.0291(7) 0.0335(8) -0.0012(5) 0.0004(6) 0.0026(5) C10 0.0341(9) 0.0470(10) 0.0372(9) 0.0070(8) 0.0010(7) -0.0048(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9377(10) 3_566 ? Cu1 O1 1.9377(10) . ? Cu1 O2 2.0983(11) 3_566 ? Cu1 O2 2.0983(11) . ? Cu1 O5 2.1596(14) 3_566 ? Cu1 O5 2.1596(14) . ? Cl1 O6 1.4296(12) . ? Cl1 O7 1.4345(12) . ? Cl1 O9 1.4458(12) . ? Cl1 O8 1.4491(13) . ? O1 C4 1.2541(18) . ? O2 C6 1.2218(19) . ? O3 C6 1.365(2) . ? O3 C9 1.3702(19) . ? O4 C7 1.3424(17) . ? O4 C2 1.3674(19) . ? O5 H5A 0.78(3) . ? O5 H5B 0.76(3) . ? C1 C2 1.489(2) . ? C1 H1A 0.98(2) . ? C1 H1B 0.95(2) . ? C1 H1C 0.93(2) . ? C2 C3 1.344(2) . ? C3 C4 1.436(2) . ? C3 H3 0.89(2) . ? C4 C5 1.445(2) . ? C5 C7 1.3793(19) . ? C5 C6 1.441(2) . ? C7 C8 1.413(2) . ? C8 C9 1.342(2) . ? C8 H8 0.89(2) . ? C9 C10 1.478(2) . ? C10 H10A 0.95(3) . ? C10 H10B 0.96(3) . ? C10 H10C 0.94(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 O1 Cu1 O1 180.00(6) 3_566 . ? O1 Cu1 O2 89.85(4) 3_566 3_566 ? O1 Cu1 O2 90.15(4) . 3_566 ? O1 Cu1 O2 90.15(4) 3_566 . ? O1 Cu1 O2 89.85(4) . . ? O2 Cu1 O2 180.0 3_566 . ? O1 Cu1 O5 88.30(5) 3_566 3_566 ? O1 Cu1 O5 91.70(5) . 3_566 ? O2 Cu1 O5 91.33(5) 3_566 3_566 ? O2 Cu1 O5 88.67(5) . 3_566 ? O1 Cu1 O5 91.70(5) 3_566 . ? O1 Cu1 O5 88.30(5) . . ? O2 Cu1 O5 88.67(5) 3_566 . ? O2 Cu1 O5 91.33(5) . . ? O5 Cu1 O5 180.0 3_566 . ? O6 Cl1 O7 110.99(8) . . ? O6 Cl1 O9 110.49(8) . . ? O7 Cl1 O9 109.60(8) . . ? O6 Cl1 O8 109.73(8) . . ? O7 Cl1 O8 109.06(8) . . ? O9 Cl1 O8 106.88(8) . . ? C4 O1 Cu1 129.95(10) . . ? C6 O2 Cu1 125.31(10) . . ? C6 O3 C9 122.93(12) . . ? C7 O4 C2 119.70(12) . . ? Cu1 O5 H5A 109.9(18) . . ? Cu1 O5 H5B 112.2(18) . . ? H5A O5 H5B 112(3) . . ? C2 C1 H1A 110.0(12) . . ? C2 C1 H1B 108.3(13) . . ? H1A C1 H1B 107.4(18) . . ? C2 C1 H1C 110.4(13) . . ? H1A C1 H1C 108.8(17) . . ? H1B C1 H1C 111.9(18) . . ? C3 C2 O4 121.60(13) . . ? C3 C2 C1 126.92(15) . . ? O4 C2 C1 111.48(13) . . ? C2 C3 C4 121.71(15) . . ? C2 C3 H3 121.2(13) . . ? C4 C3 H3 117.1(13) . . ? O1 C4 C3 119.77(14) . . ? O1 C4 C5 125.29(13) . . ? C3 C4 C5 114.94(13) . . ? C7 C5 C6 117.54(14) . . ? C7 C5 C4 119.77(13) . . ? C6 C5 C4 122.69(13) . . ? O2 C6 O3 115.12(13) . . ? O2 C6 C5 126.89(15) . . ? O3 C6 C5 117.99(13) . . ? O4 C7 C5 122.28(13) . . ? O4 C7 C8 115.50(12) . . ? C5 C7 C8 122.21(13) . . ? C9 C8 C7 118.51(14) . . ? C9 C8 H8 122.7(12) . . ? C7 C8 H8 118.7(12) . . ? C8 C9 O3 120.80(14) . . ? C8 C9 C10 126.89(15) . . ? O3 C9 C10 112.30(14) . . ? C9 C10 H10A 107.6(14) . . ? C9 C10 H10B 107.5(17) . . ? H10A C10 H10B 113(2) . . ? C9 C10 H10C 110.3(13) . . ? H10A C10 H10C 107.3(19) . . ? H10B C10 H10C 111(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C4 17(47) 3_566 . . . ? O2 Cu1 O1 C4 -179.07(13) 3_566 . . . ? O2 Cu1 O1 C4 0.93(13) . . . . ? O5 Cu1 O1 C4 89.60(13) 3_566 . . . ? O5 Cu1 O1 C4 -90.40(13) . . . . ? O1 Cu1 O2 C6 178.50(12) 3_566 . . . ? O1 Cu1 O2 C6 -1.50(12) . . . . ? O2 Cu1 O2 C6 -99(100) 3_566 . . . ? O5 Cu1 O2 C6 -93.21(13) 3_566 . . . ? O5 Cu1 O2 C6 86.79(13) . . . . ? C7 O4 C2 C3 0.4(2) . . . . ? C7 O4 C2 C1 -179.10(13) . . . . ? O4 C2 C3 C4 -0.3(2) . . . . ? C1 C2 C3 C4 179.14(15) . . . . ? Cu1 O1 C4 C3 179.05(10) . . . . ? Cu1 O1 C4 C5 -0.8(2) . . . . ? C2 C3 C4 O1 -179.93(14) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? O1 C4 C5 C7 -179.83(13) . . . . ? C3 C4 C5 C7 0.28(19) . . . . ? O1 C4 C5 C6 0.8(2) . . . . ? C3 C4 C5 C6 -179.07(13) . . . . ? Cu1 O2 C6 O3 -178.34(9) . . . . ? Cu1 O2 C6 C5 2.0(2) . . . . ? C9 O3 C6 O2 -179.44(13) . . . . ? C9 O3 C6 C5 0.2(2) . . . . ? C7 C5 C6 O2 179.08(14) . . . . ? C4 C5 C6 O2 -1.6(2) . . . . ? C7 C5 C6 O3 -0.53(19) . . . . ? C4 C5 C6 O3 178.84(12) . . . . ? C2 O4 C7 C5 -0.2(2) . . . . ? C2 O4 C7 C8 179.22(12) . . . . ? C6 C5 C7 O4 179.20(12) . . . . ? C4 C5 C7 O4 -0.2(2) . . . . ? C6 C5 C7 C8 -0.2(2) . . . . ? C4 C5 C7 C8 -179.55(13) . . . . ? O4 C7 C8 C9 -178.21(13) . . . . ? C5 C7 C8 C9 1.2(2) . . . . ? C7 C8 C9 O3 -1.5(2) . . . . ? C7 C8 C9 C10 177.18(15) . . . . ? C6 O3 C9 C8 0.9(2) . . . . ? C6 O3 C9 C10 -178.02(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O8 0.78(3) 2.07(3) 2.847(2) 175(3) 1_455 O5 H5B O9 0.76(3) 2.06(3) 2.8061(19) 170(3) 4_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.312 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.051 # Attachment '9b-jw43.cif' data_jw43 _database_code_depnum_ccdc_archive 'CCDC 774948' #TrackingRef '9b-jw43.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl2 Co O18' _chemical_formula_weight 678.19 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.033(6) _cell_length_b 12.586(8) _cell_length_c 10.332(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.922(9) _cell_angle_gamma 90.00 _cell_volume 1297.7(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2841 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.17 _exptl_crystal_description block _exptl_crystal_colour ping _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 690 _exptl_absorpt_coefficient_mu 0.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8394 _exptl_absorpt_correction_T_max 0.8941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11277 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2279 _reflns_number_gt 1819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0603P)^2^+2.7290P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2279 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Co1 Co 0.0000 0.5000 0.0000 0.0319(3) Uani 1 2 d S . . Cl1 Cl 0.57475(10) 0.68534(8) 0.77571(10) 0.0349(3) Uani 1 1 d . . . O1 O 0.1746(3) 0.5847(2) 0.0072(3) 0.0377(7) Uani 1 1 d . . . O2 O 0.0431(3) 0.4759(2) 0.1980(3) 0.0345(7) Uani 1 1 d . . . O3 O 0.1419(3) 0.4779(2) 0.3950(3) 0.0354(7) Uani 1 1 d . . . O4 O 0.4537(3) 0.6578(2) 0.3047(3) 0.0352(7) Uani 1 1 d . . . O5 O 0.1056(4) 0.3652(3) -0.0392(4) 0.0458(9) Uani 1 1 d . . . O6 O 0.5772(4) 0.7005(3) 0.6378(3) 0.0667(11) Uani 1 1 d . . . O7 O 0.7127(4) 0.6788(3) 0.8259(4) 0.0733(12) Uani 1 1 d . . . O8 O 0.5159(4) 0.7766(3) 0.8259(4) 0.0700(12) Uani 1 1 d . . . O9 O 0.5042(4) 0.5910(3) 0.7999(4) 0.0602(10) Uani 1 1 d . . . C1 C 0.5871(5) 0.7550(4) 0.1724(6) 0.0434(12) Uani 1 1 d . . . C2 C 0.4655(4) 0.6919(3) 0.1808(4) 0.0370(10) Uani 1 1 d . . . C3 C 0.3723(4) 0.6684(4) 0.0848(5) 0.0338(10) Uani 1 1 d . . . C4 C 0.2580(4) 0.6060(3) 0.1014(4) 0.0329(10) Uani 1 1 d . . . C5 C 0.2486(4) 0.5710(3) 0.2326(4) 0.0296(9) Uani 1 1 d . . . C6 C 0.1401(4) 0.5078(3) 0.2683(4) 0.0304(9) Uani 1 1 d . . . C7 C 0.3462(4) 0.5986(3) 0.3292(4) 0.0309(9) Uani 1 1 d . . . C8 C 0.3419(4) 0.5672(3) 0.4595(4) 0.0316(9) Uani 1 1 d . . . C9 C 0.2414(4) 0.5075(3) 0.4892(4) 0.0337(9) Uani 1 1 d . . . C10 C 0.2228(6) 0.4630(5) 0.6164(5) 0.0457(12) Uani 1 1 d . . . H1A H 0.662(5) 0.717(4) 0.193(5) 0.046(14) Uiso 1 1 d . . . H1B H 0.581(6) 0.789(4) 0.088(6) 0.067(17) Uiso 1 1 d . . . H1C H 0.600(6) 0.804(5) 0.238(6) 0.065(18) Uiso 1 1 d . . . H3 H 0.384(5) 0.692(4) 0.013(5) 0.057(17) Uiso 1 1 d . . . H5OA H 0.074(5) 0.323(4) -0.063(5) 0.031(17) Uiso 1 1 d . . . H5OB H 0.166(7) 0.348(6) 0.001(7) 0.09(3) Uiso 1 1 d . . . H8 H 0.402(5) 0.581(4) 0.508(5) 0.048(15) Uiso 1 1 d . . . H10A H 0.228(6) 0.396(5) 0.612(6) 0.07(2) Uiso 1 1 d . . . H10B H 0.290(5) 0.486(3) 0.676(5) 0.037(12) Uiso 1 1 d . . . H10C H 0.129(7) 0.485(5) 0.640(6) 0.081(19) Uiso 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 Co1 0.0261(4) 0.0379(5) 0.0305(4) -0.0025(4) -0.0029(3) -0.0016(3) Cl1 0.0350(6) 0.0306(5) 0.0377(6) -0.0013(4) -0.0025(4) 0.0035(4) O1 0.0319(16) 0.0472(18) 0.0332(16) 0.0020(14) -0.0013(13) -0.0041(13) O2 0.0261(15) 0.0435(18) 0.0324(16) -0.0003(13) -0.0036(12) -0.0066(12) O3 0.0312(16) 0.0382(17) 0.0354(16) 0.0029(13) -0.0037(13) -0.0038(12) O4 0.0302(15) 0.0335(16) 0.0406(17) 0.0007(13) -0.0023(13) -0.0050(12) O5 0.043(2) 0.043(2) 0.047(2) -0.0125(18) -0.0111(17) 0.0054(19) O6 0.080(3) 0.081(3) 0.040(2) -0.0135(19) 0.0092(18) -0.024(2) O7 0.060(2) 0.056(2) 0.094(3) 0.010(2) -0.039(2) -0.0024(19) O8 0.087(3) 0.039(2) 0.092(3) 0.012(2) 0.051(2) 0.0199(19) O9 0.060(2) 0.0375(19) 0.086(3) -0.0009(18) 0.022(2) -0.0091(16) C1 0.038(3) 0.042(3) 0.050(3) 0.004(3) 0.004(2) -0.007(2) C2 0.035(2) 0.032(2) 0.046(3) 0.002(2) 0.009(2) 0.0002(18) C3 0.028(2) 0.038(2) 0.035(2) 0.000(2) 0.0040(19) -0.0022(18) C4 0.029(2) 0.030(2) 0.038(2) -0.0017(18) -0.0014(19) 0.0053(17) C5 0.028(2) 0.027(2) 0.033(2) -0.0013(17) -0.0025(17) 0.0020(17) C6 0.030(2) 0.028(2) 0.032(2) 0.0000(18) 0.0002(18) 0.0030(17) C7 0.026(2) 0.024(2) 0.043(2) -0.0028(18) 0.0005(18) 0.0024(16) C8 0.028(2) 0.030(2) 0.034(2) -0.0005(19) -0.0094(19) 0.0001(18) C9 0.031(2) 0.031(2) 0.038(2) -0.0002(19) -0.0028(18) 0.0041(18) C10 0.044(3) 0.050(3) 0.043(3) 0.008(2) 0.000(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.045(3) 3_565 ? Co1 O1 2.045(3) . ? Co1 O5 2.062(4) . ? Co1 O5 2.062(4) 3_565 ? Co1 O2 2.069(3) 3_565 ? Co1 O2 2.069(3) . ? Cl1 O8 1.414(4) . ? Cl1 O9 1.418(3) . ? Cl1 O7 1.429(4) . ? Cl1 O6 1.440(4) . ? O1 C4 1.245(5) . ? O2 C6 1.221(5) . ? O3 C6 1.360(5) . ? O3 C9 1.372(5) . ? O4 C7 1.356(5) . ? O4 C2 1.366(5) . ? O5 H5OA 0.66(5) . ? O5 H5OB 0.73(7) . ? C1 C2 1.465(6) . ? C1 H1A 0.90(5) . ? C1 H1B 0.96(6) . ? C1 H1C 0.91(6) . ? C2 C3 1.324(6) . ? C3 C4 1.415(6) . ? C3 H3 0.82(5) . ? C4 C5 1.438(6) . ? C5 C7 1.369(6) . ? C5 C6 1.427(6) . ? C7 C8 1.408(6) . ? C8 C9 1.319(6) . ? C8 H8 0.77(5) . ? C9 C10 1.458(7) . ? C10 H10A 0.85(6) . ? C10 H10B 0.91(5) . ? C10 H10C 1.04(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 O1 Co1 O1 180.0 3_565 . ? O1 Co1 O5 91.10(16) 3_565 . ? O1 Co1 O5 88.90(16) . . ? O1 Co1 O5 88.90(16) 3_565 3_565 ? O1 Co1 O5 91.10(16) . 3_565 ? O5 Co1 O5 180.0 . 3_565 ? O1 Co1 O2 87.12(11) 3_565 3_565 ? O1 Co1 O2 92.88(11) . 3_565 ? O5 Co1 O2 89.18(14) . 3_565 ? O5 Co1 O2 90.82(14) 3_565 3_565 ? O1 Co1 O2 92.88(11) 3_565 . ? O1 Co1 O2 87.12(11) . . ? O5 Co1 O2 90.82(14) . . ? O5 Co1 O2 89.18(14) 3_565 . ? O2 Co1 O2 180.00(16) 3_565 . ? O8 Cl1 O9 112.3(2) . . ? O8 Cl1 O7 109.8(3) . . ? O9 Cl1 O7 111.7(2) . . ? O8 Cl1 O6 107.8(2) . . ? O9 Cl1 O6 110.2(2) . . ? O7 Cl1 O6 104.6(3) . . ? C4 O1 Co1 130.1(3) . . ? C6 O2 Co1 127.7(3) . . ? C6 O3 C9 123.0(3) . . ? C7 O4 C2 119.7(3) . . ? Co1 O5 H5OA 121(5) . . ? Co1 O5 H5OB 123(6) . . ? H5OA O5 H5OB 108(7) . . ? C2 C1 H1A 112(3) . . ? C2 C1 H1B 108(3) . . ? H1A C1 H1B 115(5) . . ? C2 C1 H1C 112(4) . . ? H1A C1 H1C 97(5) . . ? H1B C1 H1C 111(5) . . ? C3 C2 O4 120.6(4) . . ? C3 C2 C1 127.1(5) . . ? O4 C2 C1 112.3(4) . . ? C2 C3 C4 123.5(4) . . ? C2 C3 H3 116(4) . . ? C4 C3 H3 120(4) . . ? O1 C4 C3 120.9(4) . . ? O1 C4 C5 124.5(4) . . ? C3 C4 C5 114.6(4) . . ? C7 C5 C6 117.4(4) . . ? C7 C5 C4 119.9(4) . . ? C6 C5 C4 122.7(4) . . ? O2 C6 O3 114.3(4) . . ? O2 C6 C5 127.8(4) . . ? O3 C6 C5 117.9(3) . . ? O4 C7 C5 121.7(4) . . ? O4 C7 C8 115.9(4) . . ? C5 C7 C8 122.4(4) . . ? C9 C8 C7 118.9(4) . . ? C9 C8 H8 123(4) . . ? C7 C8 H8 118(4) . . ? C8 C9 O3 120.4(4) . . ? C8 C9 C10 126.9(4) . . ? O3 C9 C10 112.6(4) . . ? C9 C10 H10A 108(4) . . ? C9 C10 H10B 109(3) . . ? H10A C10 H10B 109(5) . . ? C9 C10 H10C 109(3) . . ? H10A C10 H10C 110(5) . . ? H10B C10 H10C 112(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Co1 O1 C4 -6(100) 3_565 . . . ? O5 Co1 O1 C4 -91.9(4) . . . . ? O5 Co1 O1 C4 88.1(4) 3_565 . . . ? O2 Co1 O1 C4 178.9(4) 3_565 . . . ? O2 Co1 O1 C4 -1.1(4) . . . . ? O1 Co1 O2 C6 -179.9(3) 3_565 . . . ? O1 Co1 O2 C6 0.1(3) . . . . ? O5 Co1 O2 C6 88.9(4) . . . . ? O5 Co1 O2 C6 -91.1(4) 3_565 . . . ? O2 Co1 O2 C6 -142(3) 3_565 . . . ? C7 O4 C2 C3 0.6(6) . . . . ? C7 O4 C2 C1 179.8(4) . . . . ? O4 C2 C3 C4 -1.4(7) . . . . ? C1 C2 C3 C4 179.5(5) . . . . ? Co1 O1 C4 C3 -178.8(3) . . . . ? Co1 O1 C4 C5 1.4(6) . . . . ? C2 C3 C4 O1 -178.7(4) . . . . ? C2 C3 C4 C5 1.1(6) . . . . ? O1 C4 C5 C7 179.8(4) . . . . ? C3 C4 C5 C7 -0.1(6) . . . . ? O1 C4 C5 C6 -0.5(6) . . . . ? C3 C4 C5 C6 179.7(4) . . . . ? Co1 O2 C6 O3 -179.2(2) . . . . ? Co1 O2 C6 C5 0.6(6) . . . . ? C9 O3 C6 O2 -178.9(3) . . . . ? C9 O3 C6 C5 1.3(5) . . . . ? C7 C5 C6 O2 179.2(4) . . . . ? C4 C5 C6 O2 -0.6(7) . . . . ? C7 C5 C6 O3 -1.0(5) . . . . ? C4 C5 C6 O3 179.2(3) . . . . ? C2 O4 C7 C5 0.5(6) . . . . ? C2 O4 C7 C8 -179.8(4) . . . . ? C6 C5 C7 O4 179.5(3) . . . . ? C4 C5 C7 O4 -0.7(6) . . . . ? C6 C5 C7 C8 -0.1(6) . . . . ? C4 C5 C7 C8 179.6(4) . . . . ? O4 C7 C8 C9 -178.5(4) . . . . ? C5 C7 C8 C9 1.1(6) . . . . ? C7 C8 C9 O3 -0.9(6) . . . . ? C7 C8 C9 C10 176.9(4) . . . . ? C6 O3 C9 C8 -0.3(6) . . . . ? C6 O3 C9 C10 -178.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5OA O6 0.66(5) 2.24(5) 2.883(7) 166(6) 2_545 O5 H5OB O7 0.73(7) 2.08(7) 2.768(6) 156(7) 3_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.924 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.080 # Attachment '9c-jw42.cif' data_jw42 _database_code_depnum_ccdc_archive 'CCDC 774949' #TrackingRef '9c-jw42.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl2 Ni O18' _chemical_formula_weight 677.97 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.952(3) _cell_length_b 12.636(3) _cell_length_c 10.439(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.348(4) _cell_angle_gamma 90.00 _cell_volume 1307.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3869 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8278 _exptl_absorpt_correction_T_max 0.9127 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12556 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2852 _reflns_number_gt 2441 _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. ; _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^)+(0.0379P)^2^+0.4549P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2852 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 Ni1 Ni 0.0000 0.5000 0.5000 0.02290(11) Uani 1 2 d S . . Cl1 Cl 0.42578(5) 0.68571(4) 0.73049(5) 0.02996(13) Uani 1 1 d . . . O1 O 0.16431(13) 0.41743(11) 0.50433(13) 0.0329(3) Uani 1 1 d . . . O2 O 0.03623(14) 0.52700(11) 0.69827(14) 0.0330(3) Uani 1 1 d . . . O3 O 0.13854(14) 0.52468(11) 0.89255(13) 0.0317(3) Uani 1 1 d . . . O4 O 0.44977(13) 0.34326(11) 0.79493(13) 0.0297(3) Uani 1 1 d . . . O5 O 0.11717(18) 0.63772(14) 0.45810(16) 0.0446(4) Uani 1 1 d . . . O6 O 0.43082(17) 0.70114(13) 0.86797(15) 0.0451(4) Uani 1 1 d . . . O7 O 0.28520(16) 0.67761(13) 0.68318(16) 0.0451(4) Uani 1 1 d . . . O8 O 0.49589(17) 0.59111(13) 0.70377(18) 0.0513(4) Uani 1 1 d . . . O9 O 0.48430(16) 0.77560(12) 0.67377(16) 0.0444(4) Uani 1 1 d . . . C1 C 0.5857(2) 0.24731(19) 0.6624(2) 0.0371(5) Uani 1 1 d . . . C2 C 0.46022(19) 0.30995(15) 0.6712(2) 0.0293(4) Uani 1 1 d . . . C3 C 0.3659(2) 0.33430(17) 0.5759(2) 0.0309(4) Uani 1 1 d . . . C4 C 0.25057(19) 0.39644(15) 0.59689(19) 0.0282(4) Uani 1 1 d . . . C5 C 0.24295(18) 0.43063(15) 0.72773(18) 0.0263(4) Uani 1 1 d . . . C6 C 0.13449(19) 0.49494(15) 0.7665(2) 0.0281(4) Uani 1 1 d . . . C7 C 0.34332(18) 0.40213(15) 0.82119(19) 0.0268(4) Uani 1 1 d . . . C8 C 0.3418(2) 0.43400(16) 0.9504(2) 0.0294(4) Uani 1 1 d . . . C9 C 0.2411(2) 0.49537(15) 0.9828(2) 0.0310(4) Uani 1 1 d . . . C10 C 0.2243(3) 0.5403(2) 1.1105(2) 0.0418(5) Uani 1 1 d . . . H1A H 0.593(3) 0.191(2) 0.731(3) 0.054(8) Uiso 1 1 d . . . H1B H 0.664(3) 0.294(2) 0.681(3) 0.059(8) Uiso 1 1 d . . . H1C H 0.582(3) 0.214(2) 0.575(3) 0.051(7) Uiso 1 1 d . . . H3 H 0.374(2) 0.3113(17) 0.498(2) 0.035(6) Uiso 1 1 d . . . H5A H 0.181(4) 0.661(3) 0.525(4) 0.102(12) Uiso 1 1 d . . . H5B H 0.067(3) 0.687(3) 0.437(3) 0.074(11) Uiso 1 1 d . . . H8 H 0.408(2) 0.4123(18) 1.008(2) 0.037(6) Uiso 1 1 d . . . H10A H 0.295(4) 0.518(2) 1.173(3) 0.073(10) Uiso 1 1 d . . . H10B H 0.135(4) 0.521(3) 1.136(3) 0.094(12) Uiso 1 1 d . . . H10C H 0.231(3) 0.617(2) 1.102(2) 0.061(8) Uiso 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 Ni1 0.01765(17) 0.0291(2) 0.02124(17) 0.00131(13) -0.00191(12) 0.00239(13) Cl1 0.0280(2) 0.0271(2) 0.0344(3) 0.00029(18) 0.00089(19) -0.00141(18) O1 0.0263(7) 0.0409(8) 0.0311(7) 0.0029(6) 0.0005(6) 0.0053(6) O2 0.0241(7) 0.0370(8) 0.0373(8) 0.0005(6) -0.0006(6) 0.0066(6) O3 0.0236(7) 0.0360(8) 0.0350(8) -0.0014(6) 0.0000(6) 0.0043(6) O4 0.0219(7) 0.0305(7) 0.0364(8) 0.0027(6) 0.0018(6) 0.0048(6) O5 0.0428(9) 0.0457(10) 0.0426(9) 0.0029(8) -0.0112(7) 0.0030(8) O6 0.0459(9) 0.0545(10) 0.0340(8) 0.0047(7) -0.0018(7) 0.0037(8) O7 0.0343(8) 0.0436(9) 0.0545(10) -0.0027(7) -0.0111(7) -0.0036(7) O8 0.0464(10) 0.0334(9) 0.0764(12) -0.0038(8) 0.0184(9) 0.0059(7) O9 0.0502(10) 0.0334(8) 0.0522(10) -0.0001(7) 0.0179(8) -0.0096(7) C1 0.0280(11) 0.0394(13) 0.0439(13) 0.0001(10) 0.0038(9) 0.0082(9) C2 0.0237(10) 0.0259(10) 0.0389(11) 0.0007(8) 0.0061(8) -0.0015(8) C3 0.0265(10) 0.0330(11) 0.0335(11) -0.0006(8) 0.0050(8) 0.0009(8) C4 0.0219(9) 0.0275(10) 0.0354(10) 0.0046(8) 0.0033(8) -0.0019(8) C5 0.0202(9) 0.0262(10) 0.0323(10) 0.0025(8) 0.0019(7) -0.0005(7) C6 0.0231(9) 0.0258(10) 0.0353(10) 0.0022(8) 0.0017(8) -0.0022(8) C7 0.0198(9) 0.0234(10) 0.0374(10) 0.0031(8) 0.0037(8) -0.0014(7) C8 0.0229(9) 0.0298(10) 0.0345(10) 0.0039(8) -0.0025(8) 0.0002(8) C9 0.0253(10) 0.0300(10) 0.0370(11) 0.0019(8) -0.0007(8) -0.0034(8) C10 0.0372(13) 0.0478(15) 0.0402(13) -0.0059(11) 0.0015(10) 0.0036(11) _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 Ni1 O1 1.9366(14) . ? Ni1 O1 1.9366(14) 3_566 ? Ni1 O2 2.0955(15) 3_566 ? Ni1 O2 2.0955(15) . ? Ni1 O5 2.1621(18) 3_566 ? Ni1 O5 2.1621(18) . ? Cl1 O8 1.4247(16) . ? Cl1 O9 1.4298(16) . ? Cl1 O7 1.4432(16) . ? Cl1 O6 1.4446(16) . ? O1 C4 1.259(2) . ? O2 C6 1.224(2) . ? O3 C6 1.365(3) . ? O3 C9 1.374(2) . ? O4 C7 1.343(2) . ? O4 C2 1.371(2) . ? O5 H5A 0.95(4) . ? O5 H5B 0.82(3) . ? C1 C2 1.489(3) . ? C1 H1A 1.01(3) . ? C1 H1B 0.98(3) . ? C1 H1C 1.00(3) . ? C2 C3 1.339(3) . ? C3 C4 1.425(3) . ? C3 H3 0.88(2) . ? C4 C5 1.441(3) . ? C5 C7 1.377(3) . ? C5 C6 1.439(3) . ? C7 C8 1.409(3) . ? C8 C9 1.335(3) . ? C8 H8 0.89(2) . ? C9 C10 1.474(3) . ? C10 H10A 0.96(4) . ? C10 H10B 0.98(4) . ? C10 H10C 0.97(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 O1 Ni1 O1 180.00(8) . 3_566 ? O1 Ni1 O2 90.15(5) . 3_566 ? O1 Ni1 O2 89.85(6) 3_566 3_566 ? O1 Ni1 O2 89.85(6) . . ? O1 Ni1 O2 90.15(5) 3_566 . ? O2 Ni1 O2 180.0 3_566 . ? O1 Ni1 O5 91.82(7) . 3_566 ? O1 Ni1 O5 88.18(7) 3_566 3_566 ? O2 Ni1 O5 91.28(6) 3_566 3_566 ? O2 Ni1 O5 88.72(6) . 3_566 ? O1 Ni1 O5 88.18(7) . . ? O1 Ni1 O5 91.82(7) 3_566 . ? O2 Ni1 O5 88.72(6) 3_566 . ? O2 Ni1 O5 91.28(6) . . ? O5 Ni1 O5 180.0 3_566 . ? O8 Cl1 O9 111.08(10) . . ? O8 Cl1 O7 110.51(10) . . ? O9 Cl1 O7 109.51(10) . . ? O8 Cl1 O6 109.60(10) . . ? O9 Cl1 O6 109.05(10) . . ? O7 Cl1 O6 106.99(10) . . ? C4 O1 Ni1 130.17(13) . . ? C6 O2 Ni1 125.15(14) . . ? C6 O3 C9 122.67(16) . . ? C7 O4 C2 119.51(15) . . ? Ni1 O5 H5A 116(2) . . ? Ni1 O5 H5B 110(2) . . ? H5A O5 H5B 109(3) . . ? C2 C1 H1A 109.8(15) . . ? C2 C1 H1B 108.6(16) . . ? H1A C1 H1B 106(2) . . ? C2 C1 H1C 108.5(15) . . ? H1A C1 H1C 110(2) . . ? H1B C1 H1C 113(2) . . ? C3 C2 O4 121.36(18) . . ? C3 C2 C1 127.6(2) . . ? O4 C2 C1 111.06(17) . . ? C2 C3 C4 122.1(2) . . ? C2 C3 H3 119.9(15) . . ? C4 C3 H3 118.1(15) . . ? O1 C4 C3 119.95(19) . . ? O1 C4 C5 124.86(18) . . ? C3 C4 C5 115.19(17) . . ? C7 C5 C6 117.49(18) . . ? C7 C5 C4 119.61(17) . . ? C6 C5 C4 122.90(17) . . ? O2 C6 O3 114.85(17) . . ? O2 C6 C5 127.04(19) . . ? O3 C6 C5 118.11(17) . . ? O4 C7 C5 122.26(18) . . ? O4 C7 C8 115.63(17) . . ? C5 C7 C8 122.10(18) . . ? C9 C8 C7 118.93(18) . . ? C9 C8 H8 122.3(14) . . ? C7 C8 H8 118.8(14) . . ? C8 C9 O3 120.67(19) . . ? C8 C9 C10 127.2(2) . . ? O3 C9 C10 112.11(18) . . ? C9 C10 H10A 111.2(19) . . ? C9 C10 H10B 109(2) . . ? H10A C10 H10B 112(3) . . ? C9 C10 H10C 106.8(16) . . ? H10A C10 H10C 107(2) . . ? H10B C10 H10C 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 O1 C4 28(100) 3_566 . . . ? O2 Ni1 O1 C4 178.96(17) 3_566 . . . ? O2 Ni1 O1 C4 -1.04(17) . . . . ? O5 Ni1 O1 C4 -89.75(17) 3_566 . . . ? O5 Ni1 O1 C4 90.25(17) . . . . ? O1 Ni1 O2 C6 1.35(16) . . . . ? O1 Ni1 O2 C6 -178.65(16) 3_566 . . . ? O2 Ni1 O2 C6 -74(89) 3_566 . . . ? O5 Ni1 O2 C6 93.18(17) 3_566 . . . ? O5 Ni1 O2 C6 -86.82(17) . . . . ? C7 O4 C2 C3 -0.4(3) . . . . ? C7 O4 C2 C1 179.24(17) . . . . ? O4 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 C4 -179.1(2) . . . . ? Ni1 O1 C4 C3 -179.13(14) . . . . ? Ni1 O1 C4 C5 1.1(3) . . . . ? C2 C3 C4 O1 -179.97(19) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? O1 C4 C5 C7 179.61(18) . . . . ? C3 C4 C5 C7 -0.2(3) . . . . ? O1 C4 C5 C6 -0.9(3) . . . . ? C3 C4 C5 C6 179.28(18) . . . . ? Ni1 O2 C6 O3 178.32(11) . . . . ? Ni1 O2 C6 C5 -1.7(3) . . . . ? C9 O3 C6 O2 179.68(17) . . . . ? C9 O3 C6 C5 -0.3(3) . . . . ? C7 C5 C6 O2 -179.14(19) . . . . ? C4 C5 C6 O2 1.4(3) . . . . ? C7 C5 C6 O3 0.8(3) . . . . ? C4 C5 C6 O3 -178.70(17) . . . . ? C2 O4 C7 C5 0.1(3) . . . . ? C2 O4 C7 C8 -179.18(16) . . . . ? C6 C5 C7 O4 -179.26(17) . . . . ? C4 C5 C7 O4 0.3(3) . . . . ? C6 C5 C7 C8 -0.1(3) . . . . ? C4 C5 C7 C8 179.44(17) . . . . ? O4 C7 C8 C9 178.00(17) . . . . ? C5 C7 C8 C9 -1.2(3) . . . . ? C7 C8 C9 O3 1.8(3) . . . . ? C7 C8 C9 C10 -177.3(2) . . . . ? C6 O3 C9 C8 -1.1(3) . . . . ? C6 O3 C9 C10 178.18(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5B O6 0.82(3) 2.04(3) 2.854(3) 173(3) 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.327 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.055 # Attachment '9d-jw54.cif' data_jw54 _database_code_depnum_ccdc_archive 'CCDC 774950' #TrackingRef '9d-jw54.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl2 O18 Zn' _chemical_formula_weight 684.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.973(3) _cell_length_b 12.636(3) _cell_length_c 10.432(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.500(4) _cell_angle_gamma 90.00 _cell_volume 1308.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3293 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 23.64 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6944 _exptl_absorpt_correction_T_max 0.9080 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14755 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2855 _reflns_number_gt 2314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0501P)^2^+0.7927P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2855 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 Zn1 Zn 0.5000 0.0000 0.0000 0.02987(15) Uani 1 2 d S . . Cl1 Cl 0.92550(7) -0.18614(5) 0.22722(7) 0.03144(18) Uani 1 1 d . . . O1 O 0.67435(19) 0.08513(16) 0.00538(18) 0.0343(5) Uani 1 1 d . . . O2 O 0.54122(19) -0.02380(16) 0.19723(18) 0.0311(4) Uani 1 1 d . . . O3 O 0.64096(19) -0.02224(15) 0.39242(18) 0.0310(4) Uani 1 1 d . . . O4 O 0.95463(18) 0.15816(15) 0.30130(18) 0.0308(4) Uani 1 1 d . . . O5 O 0.6090(3) -0.1354(2) -0.0395(2) 0.0417(6) Uani 1 1 d . . . O6 O 0.9269(2) -0.20290(19) 0.3645(2) 0.0497(6) Uani 1 1 d . . . O7 O 0.7856(2) -0.17671(18) 0.1792(2) 0.0524(6) Uani 1 1 d . . . O8 O 0.9977(2) -0.09214(18) 0.2031(2) 0.0526(6) Uani 1 1 d . . . O9 O 0.9823(2) -0.27709(18) 0.1716(2) 0.0516(6) Uani 1 1 d . . . C1 C 1.0911(3) 0.2555(3) 0.1709(4) 0.0399(7) Uani 1 1 d . . . C2 C 0.9669(3) 0.1922(2) 0.1778(3) 0.0329(6) Uani 1 1 d . . . C3 C 0.8743(3) 0.1691(2) 0.0816(3) 0.0326(6) Uani 1 1 d . . . C4 C 0.7582(3) 0.1062(2) 0.0987(3) 0.0294(6) Uani 1 1 d . . . C5 C 0.7481(3) 0.0715(2) 0.2303(3) 0.0261(5) Uani 1 1 d . . . C6 C 0.6397(3) 0.0080(2) 0.2666(3) 0.0272(6) Uani 1 1 d . . . C7 C 0.8470(3) 0.0989(2) 0.3251(3) 0.0273(6) Uani 1 1 d . . . C8 C 0.8428(3) 0.0676(2) 0.4547(3) 0.0292(6) Uani 1 1 d . . . C9 C 0.7418(3) 0.0066(2) 0.4848(3) 0.0301(6) Uani 1 1 d . . . C10 C 0.7226(4) -0.0388(3) 0.6114(3) 0.0399(7) Uani 1 1 d . . . H1A H 1.095(3) 0.308(3) 0.234(4) 0.050(10) Uiso 1 1 d . . . H1B H 1.093(3) 0.290(3) 0.088(3) 0.044(9) Uiso 1 1 d . . . H1C H 1.166(4) 0.214(3) 0.188(3) 0.047(10) Uiso 1 1 d . . . H3 H 0.888(3) 0.194(2) 0.003(3) 0.031(8) Uiso 1 1 d . . . H5A H 0.661(4) -0.151(3) 0.006(4) 0.051(13) Uiso 1 1 d . . . H5B H 0.567(5) -0.180(3) -0.063(4) 0.067(16) Uiso 1 1 d . . . H8 H 0.906(4) 0.085(3) 0.507(3) 0.041(9) Uiso 1 1 d . . . H10A H 0.723(4) -0.112(3) 0.607(4) 0.063(12) Uiso 1 1 d . . . H10B H 0.636(5) -0.019(3) 0.634(4) 0.068(13) Uiso 1 1 d . . . H10C H 0.787(4) -0.015(2) 0.672(3) 0.039(9) Uiso 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 Zn1 0.0245(2) 0.0382(3) 0.0255(2) -0.00231(19) -0.00470(17) -0.00093(19) Cl1 0.0294(3) 0.0303(4) 0.0335(4) -0.0005(3) -0.0029(3) 0.0026(3) O1 0.0287(10) 0.0469(12) 0.0263(10) 0.0016(9) -0.0026(8) -0.0051(9) O2 0.0242(10) 0.0416(11) 0.0263(10) 0.0008(8) -0.0040(8) -0.0063(8) O3 0.0264(10) 0.0381(11) 0.0272(10) 0.0011(8) -0.0040(8) -0.0034(8) O4 0.0247(9) 0.0342(10) 0.0326(11) -0.0008(8) -0.0030(8) -0.0051(8) O5 0.0368(13) 0.0460(15) 0.0393(13) -0.0079(11) -0.0126(11) 0.0061(12) O6 0.0521(14) 0.0611(15) 0.0347(12) -0.0058(10) -0.0024(10) -0.0088(12) O7 0.0409(13) 0.0486(14) 0.0628(16) 0.0025(12) -0.0208(11) 0.0024(10) O8 0.0474(14) 0.0396(13) 0.0725(17) 0.0015(11) 0.0149(12) -0.0060(10) O9 0.0596(15) 0.0372(12) 0.0617(15) 0.0035(11) 0.0244(12) 0.0101(11) C1 0.0328(17) 0.0429(19) 0.0441(19) 0.0029(16) 0.0048(14) -0.0051(14) C2 0.0279(14) 0.0332(15) 0.0379(16) 0.0026(12) 0.0037(12) 0.0014(11) C3 0.0322(15) 0.0343(15) 0.0316(15) 0.0014(12) 0.0045(12) -0.0008(12) C4 0.0252(13) 0.0316(15) 0.0313(14) -0.0013(11) 0.0019(11) 0.0033(11) C5 0.0224(12) 0.0259(13) 0.0291(14) 0.0001(11) -0.0013(10) 0.0017(10) C6 0.0267(13) 0.0273(14) 0.0269(13) -0.0010(11) -0.0015(11) 0.0041(11) C7 0.0229(13) 0.0243(14) 0.0340(15) -0.0018(11) -0.0007(11) 0.0019(10) C8 0.0258(14) 0.0306(14) 0.0293(14) -0.0017(12) -0.0079(11) 0.0012(11) C9 0.0281(14) 0.0323(15) 0.0283(14) -0.0018(11) -0.0052(11) 0.0031(12) C10 0.0375(18) 0.050(2) 0.0308(16) 0.0051(15) -0.0042(14) -0.0042(15) _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 2.0408(19) 3_655 ? Zn1 O1 2.0408(19) . ? Zn1 O2 2.0809(19) 3_655 ? Zn1 O2 2.0809(19) . ? Zn1 O5 2.089(3) 3_655 ? Zn1 O5 2.089(3) . ? Cl1 O8 1.424(2) . ? Cl1 O9 1.429(2) . ? Cl1 O7 1.442(2) . ? Cl1 O6 1.446(2) . ? O1 C4 1.250(3) . ? O2 C6 1.230(3) . ? O3 C6 1.366(3) . ? O3 C9 1.374(3) . ? O4 C7 1.351(3) . ? O4 C2 1.375(3) . ? O5 H5A 0.70(4) . ? O5 H5B 0.73(4) . ? C1 C2 1.482(4) . ? C1 H1A 0.93(4) . ? C1 H1B 0.97(4) . ? C1 H1C 0.92(4) . ? C2 C3 1.330(4) . ? C3 C4 1.429(4) . ? C3 H3 0.90(3) . ? C4 C5 1.455(4) . ? C5 C7 1.372(4) . ? C5 C6 1.426(4) . ? C7 C8 1.414(4) . ? C8 C9 1.330(4) . ? C8 H8 0.82(3) . ? C9 C10 1.469(4) . ? C10 H10A 0.93(4) . ? C10 H10B 0.95(5) . ? C10 H10C 0.91(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 180.00(11) 3_655 . ? O1 Zn1 O2 87.82(7) 3_655 3_655 ? O1 Zn1 O2 92.18(7) . 3_655 ? O1 Zn1 O2 92.18(7) 3_655 . ? O1 Zn1 O2 87.82(7) . . ? O2 Zn1 O2 180.00(11) 3_655 . ? O1 Zn1 O5 88.80(10) 3_655 3_655 ? O1 Zn1 O5 91.20(10) . 3_655 ? O2 Zn1 O5 91.11(9) 3_655 3_655 ? O2 Zn1 O5 88.89(9) . 3_655 ? O1 Zn1 O5 91.20(10) 3_655 . ? O1 Zn1 O5 88.80(10) . . ? O2 Zn1 O5 88.89(9) 3_655 . ? O2 Zn1 O5 91.11(9) . . ? O5 Zn1 O5 180.00(18) 3_655 . ? O8 Cl1 O9 111.87(14) . . ? O8 Cl1 O7 111.01(15) . . ? O9 Cl1 O7 109.51(15) . . ? O8 Cl1 O6 109.87(15) . . ? O9 Cl1 O6 108.51(14) . . ? O7 Cl1 O6 105.87(15) . . ? C4 O1 Zn1 129.72(18) . . ? C6 O2 Zn1 127.26(18) . . ? C6 O3 C9 122.6(2) . . ? C7 O4 C2 119.3(2) . . ? Zn1 O5 H5A 118(3) . . ? Zn1 O5 H5B 114(4) . . ? H5A O5 H5B 112(5) . . ? C2 C1 H1A 109(2) . . ? C2 C1 H1B 112(2) . . ? H1A C1 H1B 108(3) . . ? C2 C1 H1C 111(2) . . ? H1A C1 H1C 107(3) . . ? H1B C1 H1C 110(3) . . ? C3 C2 O4 121.3(3) . . ? C3 C2 C1 127.3(3) . . ? O4 C2 C1 111.4(3) . . ? C2 C3 C4 122.7(3) . . ? C2 C3 H3 117.1(19) . . ? C4 C3 H3 120.1(19) . . ? O1 C4 C3 120.8(3) . . ? O1 C4 C5 124.7(3) . . ? C3 C4 C5 114.6(2) . . ? C7 C5 C6 117.5(2) . . ? C7 C5 C4 119.5(2) . . ? C6 C5 C4 122.9(2) . . ? O2 C6 O3 114.0(2) . . ? O2 C6 C5 127.6(3) . . ? O3 C6 C5 118.4(2) . . ? O4 C7 C5 122.5(2) . . ? O4 C7 C8 115.3(2) . . ? C5 C7 C8 122.2(3) . . ? C9 C8 C7 118.7(3) . . ? C9 C8 H8 123(2) . . ? C7 C8 H8 118(2) . . ? C8 C9 O3 120.6(3) . . ? C8 C9 C10 127.2(3) . . ? O3 C9 C10 112.2(3) . . ? C9 C10 H10A 110(2) . . ? C9 C10 H10B 108(2) . . ? H10A C10 H10B 107(3) . . ? C9 C10 H10C 110(2) . . ? H10A C10 H10C 111(3) . . ? H10B C10 H10C 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 O1 C4 10(100) 3_655 . . . ? O2 Zn1 O1 C4 179.7(2) 3_655 . . . ? O2 Zn1 O1 C4 -0.3(2) . . . . ? O5 Zn1 O1 C4 88.5(2) 3_655 . . . ? O5 Zn1 O1 C4 -91.5(2) . . . . ? O1 Zn1 O2 C6 179.1(2) 3_655 . . . ? O1 Zn1 O2 C6 -0.9(2) . . . . ? O2 Zn1 O2 C6 0(100) 3_655 . . . ? O5 Zn1 O2 C6 -92.1(2) 3_655 . . . ? O5 Zn1 O2 C6 87.9(2) . . . . ? C7 O4 C2 C3 0.8(4) . . . . ? C7 O4 C2 C1 -179.9(3) . . . . ? O4 C2 C3 C4 -1.3(5) . . . . ? C1 C2 C3 C4 179.4(3) . . . . ? Zn1 O1 C4 C3 -179.19(19) . . . . ? Zn1 O1 C4 C5 0.4(4) . . . . ? C2 C3 C4 O1 -179.1(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? O1 C4 C5 C7 179.6(3) . . . . ? C3 C4 C5 C7 -0.8(4) . . . . ? O1 C4 C5 C6 0.5(4) . . . . ? C3 C4 C5 C6 -179.9(3) . . . . ? Zn1 O2 C6 O3 -178.49(15) . . . . ? Zn1 O2 C6 C5 1.9(4) . . . . ? C9 O3 C6 O2 -179.2(2) . . . . ? C9 O3 C6 C5 0.4(4) . . . . ? C7 C5 C6 O2 179.1(3) . . . . ? C4 C5 C6 O2 -1.8(4) . . . . ? C7 C5 C6 O3 -0.4(4) . . . . ? C4 C5 C6 O3 178.7(2) . . . . ? C2 O4 C7 C5 -0.3(4) . . . . ? C2 O4 C7 C8 -180.0(2) . . . . ? C6 C5 C7 O4 179.5(2) . . . . ? C4 C5 C7 O4 0.4(4) . . . . ? C6 C5 C7 C8 -0.8(4) . . . . ? C4 C5 C7 C8 -180.0(2) . . . . ? O4 C7 C8 C9 -178.1(2) . . . . ? C5 C7 C8 C9 2.2(4) . . . . ? C7 C8 C9 O3 -2.2(4) . . . . ? C7 C8 C9 C10 176.6(3) . . . . ? C6 O3 C9 C8 1.0(4) . . . . ? C6 O3 C9 C10 -178.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O7 0.70(4) 2.12(4) 2.794(4) 164(4) . O5 H5B O6 0.73(4) 2.12(5) 2.851(4) 174(5) 4 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.680 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.071 # Attachment '9e-jw49.cif' data_jw49 _database_code_depnum_ccdc_archive 'CCDC 774951' #TrackingRef '9e-jw49.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl2 Fe O18' _chemical_formula_weight 675.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.113(2) _cell_length_b 12.627(3) _cell_length_c 10.339(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.402(4) _cell_angle_gamma 90.00 _cell_volume 1314.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3321 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.18 _exptl_crystal_description block _exptl_crystal_colour red/orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7295 _exptl_absorpt_correction_T_max 0.9186 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8603 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2848 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0482P)^2^+0.6030P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2848 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Fe1 Fe 0.0000 0.5000 0.5000 0.03319(14) Uani 1 2 d S . . Cl1 Cl 0.57532(5) 0.68414(4) 0.27610(5) 0.03504(15) Uani 1 1 d . . . O1 O 0.17387(14) 0.58551(13) 0.50881(14) 0.0384(3) Uani 1 1 d . . . O2 O 0.04516(14) 0.47607(12) 0.69960(13) 0.0348(3) Uani 1 1 d . . . O3 O 0.14261(14) 0.47766(12) 0.89734(14) 0.0338(3) Uani 1 1 d . . . O4 O 0.45276(13) 0.65840(12) 0.80480(14) 0.0346(3) Uani 1 1 d . . . O5 O 0.1123(2) 0.36251(16) 0.45462(19) 0.0464(4) Uani 1 1 d . . . O6 O 0.5733(2) 0.7011(2) 0.1370(2) 0.0511(6) Uani 0.849(3) 1 d P A 1 O7 O 0.7152(2) 0.67685(16) 0.3231(2) 0.0492(6) Uani 0.849(3) 1 d P A 1 O8 O 0.5206(2) 0.77691(16) 0.3308(2) 0.0485(6) Uani 0.849(3) 1 d P A 1 O6A O 0.6604(13) 0.6920(10) 0.3888(12) 0.0511(6) Uani 0.151(3) 1 d P A 2 O7A O 0.4655(13) 0.7575(11) 0.2782(13) 0.0492(6) Uani 0.151(3) 1 d P A 2 O8A O 0.6306(15) 0.6689(9) 0.1682(14) 0.0485(6) Uani 0.151(3) 1 d P A 2 O9 O 0.50526(18) 0.58976(14) 0.3018(2) 0.0596(5) Uani 1 1 d . A . C1 C 0.5869(2) 0.7558(2) 0.6727(3) 0.0433(5) Uani 1 1 d . . . C2 C 0.4641(2) 0.69315(16) 0.6809(2) 0.0346(5) Uani 1 1 d . . . C3 C 0.3720(2) 0.66944(17) 0.5842(2) 0.0349(5) Uani 1 1 d . . . C4 C 0.25771(19) 0.60699(16) 0.60194(19) 0.0323(4) Uani 1 1 d . . . C5 C 0.24900(18) 0.57159(15) 0.73412(19) 0.0294(4) Uani 1 1 d . . . C6 C 0.14117(19) 0.50758(15) 0.7710(2) 0.0299(4) Uani 1 1 d . . . C7 C 0.34702(18) 0.59943(15) 0.8298(2) 0.0297(4) Uani 1 1 d . . . C8 C 0.3425(2) 0.56687(17) 0.9600(2) 0.0319(4) Uani 1 1 d . . . C9 C 0.2424(2) 0.50647(16) 0.9903(2) 0.0329(4) Uani 1 1 d . . . C10 C 0.2235(3) 0.4616(2) 1.1186(2) 0.0448(5) Uani 1 1 d . . . H1A H 0.596(3) 0.805(2) 0.743(3) 0.060(8) Uiso 1 1 d . . . H1B H 0.584(3) 0.790(2) 0.597(3) 0.057(8) Uiso 1 1 d . . . H1C H 0.663(3) 0.712(2) 0.685(3) 0.057(8) Uiso 1 1 d . . . H3 H 0.381(2) 0.6916(19) 0.509(3) 0.044(7) Uiso 1 1 d . . . H5A H 0.075(3) 0.320(3) 0.431(3) 0.066(12) Uiso 1 1 d . . . H5B H 0.172(3) 0.344(3) 0.505(3) 0.069(10) Uiso 1 1 d . . . H8 H 0.395(3) 0.583(2) 1.010(3) 0.051(8) Uiso 1 1 d . . . H9C H 0.285(3) 0.4884(19) 1.184(3) 0.041(7) Uiso 1 1 d . . . H10A H 0.229(3) 0.386(3) 1.113(3) 0.066(9) Uiso 1 1 d . . . H10B H 0.133(4) 0.482(2) 1.144(3) 0.082(10) Uiso 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 Fe1 0.0254(2) 0.0423(3) 0.0309(2) -0.00370(17) -0.00267(16) -0.00096(16) Cl1 0.0331(3) 0.0331(3) 0.0380(3) -0.0013(2) -0.0016(2) 0.00363(19) O1 0.0301(7) 0.0509(9) 0.0336(8) -0.0001(7) 0.0000(6) -0.0051(6) O2 0.0256(7) 0.0461(8) 0.0320(7) -0.0009(6) -0.0015(6) -0.0061(6) O3 0.0275(7) 0.0396(8) 0.0336(7) 0.0009(6) -0.0017(6) -0.0033(6) O4 0.0264(7) 0.0362(8) 0.0407(8) -0.0008(6) 0.0007(6) -0.0045(6) O5 0.0393(10) 0.0493(11) 0.0475(10) -0.0115(9) -0.0115(8) 0.0081(8) O6 0.0490(13) 0.0671(15) 0.0360(11) -0.0049(10) -0.0032(9) -0.0050(11) O7 0.0376(11) 0.0500(12) 0.0565(14) 0.0030(9) -0.0139(10) 0.0042(8) O8 0.0523(13) 0.0351(10) 0.0611(14) 0.0021(9) 0.0213(11) 0.0088(9) O6A 0.0490(13) 0.0671(15) 0.0360(11) -0.0049(10) -0.0032(9) -0.0050(11) O7A 0.0376(11) 0.0500(12) 0.0565(14) 0.0030(9) -0.0139(10) 0.0042(8) O8A 0.0523(13) 0.0351(10) 0.0611(14) 0.0021(9) 0.0213(11) 0.0088(9) O9 0.0553(11) 0.0436(10) 0.0828(14) -0.0014(9) 0.0221(10) -0.0050(8) C1 0.0343(12) 0.0448(14) 0.0513(15) 0.0049(12) 0.0070(10) -0.0068(10) C2 0.0288(10) 0.0315(11) 0.0437(12) 0.0011(9) 0.0040(9) 0.0010(8) C3 0.0296(10) 0.0388(12) 0.0367(11) 0.0012(9) 0.0046(9) 0.0014(8) C4 0.0268(10) 0.0334(10) 0.0367(11) -0.0013(8) 0.0020(8) 0.0032(8) C5 0.0238(9) 0.0290(10) 0.0351(10) -0.0026(8) 0.0008(7) 0.0022(7) C6 0.0256(9) 0.0312(10) 0.0326(10) -0.0006(8) 0.0008(8) 0.0022(7) C7 0.0236(9) 0.0275(10) 0.0377(10) -0.0020(8) -0.0001(8) 0.0021(7) C8 0.0261(10) 0.0336(11) 0.0343(11) -0.0030(9) -0.0066(8) -0.0007(8) C9 0.0299(10) 0.0332(11) 0.0342(10) -0.0018(8) -0.0040(8) 0.0045(8) C10 0.0421(13) 0.0522(15) 0.0396(13) 0.0089(11) 0.0012(10) -0.0024(11) _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 Fe1 O1 2.0581(15) . ? Fe1 O1 2.0581(15) 3_566 ? Fe1 O2 2.0932(15) 3_566 ? Fe1 O2 2.0932(15) . ? Fe1 O5 2.1506(18) 3_566 ? Fe1 O5 2.1506(18) . ? Cl1 O8A 1.308(12) . ? Cl1 O6A 1.385(11) . ? Cl1 O9 1.4241(18) . ? Cl1 O8 1.434(2) . ? Cl1 O7A 1.448(12) . ? Cl1 O6 1.452(2) . ? Cl1 O7 1.4547(19) . ? O1 C4 1.251(2) . ? O2 C6 1.229(2) . ? O3 C6 1.359(2) . ? O3 C9 1.375(2) . ? O4 C7 1.348(2) . ? O4 C2 1.370(3) . ? O5 H5A 0.69(3) . ? O5 H5B 0.79(4) . ? C1 C2 1.481(3) . ? C1 H1A 0.95(3) . ? C1 H1B 0.89(3) . ? C1 H1C 0.95(3) . ? C2 C3 1.335(3) . ? C3 C4 1.425(3) . ? C3 H3 0.84(3) . ? C4 C5 1.448(3) . ? C5 C7 1.378(3) . ? C5 C6 1.437(3) . ? C7 C8 1.413(3) . ? C8 C9 1.328(3) . ? C8 H8 0.74(3) . ? C9 C10 1.471(3) . ? C10 H9C 0.94(3) . ? C10 H10A 0.95(3) . ? C10 H10B 1.01(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe1 O1 180.00(8) . 3_566 ? O1 Fe1 O2 94.25(6) . 3_566 ? O1 Fe1 O2 85.75(6) 3_566 3_566 ? O1 Fe1 O2 85.75(6) . . ? O1 Fe1 O2 94.25(6) 3_566 . ? O2 Fe1 O2 180.0 3_566 . ? O1 Fe1 O5 91.92(7) . 3_566 ? O1 Fe1 O5 88.08(7) 3_566 3_566 ? O2 Fe1 O5 91.59(7) 3_566 3_566 ? O2 Fe1 O5 88.41(7) . 3_566 ? O1 Fe1 O5 88.08(7) . . ? O1 Fe1 O5 91.92(7) 3_566 . ? O2 Fe1 O5 88.41(7) 3_566 . ? O2 Fe1 O5 91.59(7) . . ? O5 Fe1 O5 180.0 3_566 . ? O8A Cl1 O6A 116.5(9) . . ? O8A Cl1 O9 107.2(6) . . ? O6A Cl1 O9 100.6(5) . . ? O8A Cl1 O8 131.9(5) . . ? O6A Cl1 O8 80.9(6) . . ? O9 Cl1 O8 113.14(11) . . ? O8A Cl1 O7A 119.8(8) . . ? O6A Cl1 O7A 111.0(8) . . ? O9 Cl1 O7A 97.9(6) . . ? O8 Cl1 O7A 31.4(5) . . ? O8A Cl1 O6 31.1(6) . . ? O6A Cl1 O6 140.5(6) . . ? O9 Cl1 O6 110.30(13) . . ? O8 Cl1 O6 107.47(13) . . ? O7A Cl1 O6 88.9(5) . . ? O8A Cl1 O7 78.2(7) . . ? O6A Cl1 O7 38.4(6) . . ? O9 Cl1 O7 111.72(12) . . ? O8 Cl1 O7 108.62(14) . . ? O7A Cl1 O7 139.4(6) . . ? O6 Cl1 O7 105.20(13) . . ? C4 O1 Fe1 131.45(14) . . ? C6 O2 Fe1 129.19(13) . . ? C6 O3 C9 122.64(16) . . ? C7 O4 C2 119.63(16) . . ? Fe1 O5 H5A 115(3) . . ? Fe1 O5 H5B 119(2) . . ? H5A O5 H5B 111(4) . . ? C2 C1 H1A 108.9(17) . . ? C2 C1 H1B 110.4(18) . . ? H1A C1 H1B 110(2) . . ? C2 C1 H1C 110.9(17) . . ? H1A C1 H1C 105(2) . . ? H1B C1 H1C 111(2) . . ? C3 C2 O4 120.99(19) . . ? C3 C2 C1 127.4(2) . . ? O4 C2 C1 111.63(19) . . ? C2 C3 C4 123.0(2) . . ? C2 C3 H3 119.6(18) . . ? C4 C3 H3 117.4(17) . . ? O1 C4 C3 121.31(19) . . ? O1 C4 C5 124.21(18) . . ? C3 C4 C5 114.49(18) . . ? C7 C5 C6 117.73(18) . . ? C7 C5 C4 119.66(18) . . ? C6 C5 C4 122.60(18) . . ? O2 C6 O3 115.07(17) . . ? O2 C6 C5 126.79(19) . . ? O3 C6 C5 118.14(17) . . ? O4 C7 C5 122.22(18) . . ? O4 C7 C8 116.17(17) . . ? C5 C7 C8 121.61(18) . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8 121(2) . . ? C7 C8 H8 120(2) . . ? C8 C9 O3 120.81(19) . . ? C8 C9 C10 126.9(2) . . ? O3 C9 C10 112.29(19) . . ? C9 C10 H9C 112.1(15) . . ? C9 C10 H10A 108.6(18) . . ? H9C C10 H10A 111(2) . . ? C9 C10 H10B 109.8(19) . . ? H9C C10 H10B 106(2) . . ? H10A C10 H10B 109(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Fe1 O1 C4 57(100) 3_566 . . . ? O2 Fe1 O1 C4 179.34(18) 3_566 . . . ? O2 Fe1 O1 C4 -0.66(18) . . . . ? O5 Fe1 O1 C4 87.59(19) 3_566 . . . ? O5 Fe1 O1 C4 -92.41(19) . . . . ? O1 Fe1 O2 C6 -0.09(18) . . . . ? O1 Fe1 O2 C6 179.91(18) 3_566 . . . ? O2 Fe1 O2 C6 18(99) 3_566 . . . ? O5 Fe1 O2 C6 -92.13(18) 3_566 . . . ? O5 Fe1 O2 C6 87.87(18) . . . . ? C7 O4 C2 C3 -0.1(3) . . . . ? C7 O4 C2 C1 -179.57(18) . . . . ? O4 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C4 179.1(2) . . . . ? Fe1 O1 C4 C3 -179.51(14) . . . . ? Fe1 O1 C4 C5 0.8(3) . . . . ? C2 C3 C4 O1 -179.4(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? O1 C4 C5 C7 179.82(19) . . . . ? C3 C4 C5 C7 0.1(3) . . . . ? O1 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 C6 -179.81(18) . . . . ? Fe1 O2 C6 O3 -179.44(11) . . . . ? Fe1 O2 C6 C5 0.7(3) . . . . ? C9 O3 C6 O2 -179.68(17) . . . . ? C9 O3 C6 C5 0.2(3) . . . . ? C7 C5 C6 O2 179.39(19) . . . . ? C4 C5 C6 O2 -0.7(3) . . . . ? C7 C5 C6 O3 -0.5(3) . . . . ? C4 C5 C6 O3 179.45(17) . . . . ? C2 O4 C7 C5 0.5(3) . . . . ? C2 O4 C7 C8 -179.89(17) . . . . ? C6 C5 C7 O4 179.38(17) . . . . ? C4 C5 C7 O4 -0.6(3) . . . . ? C6 C5 C7 C8 -0.2(3) . . . . ? C4 C5 C7 C8 179.88(18) . . . . ? O4 C7 C8 C9 -178.43(18) . . . . ? C5 C7 C8 C9 1.2(3) . . . . ? C7 C8 C9 O3 -1.4(3) . . . . ? C7 C8 C9 C10 177.4(2) . . . . ? C6 O3 C9 C8 0.8(3) . . . . ? C6 O3 C9 C10 -178.24(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O6 0.69(3) 2.19(4) 2.871(4) 170(4) 2_545 O5 H5A O7A 0.69(3) 2.30(4) 2.796(13) 130(4) 2_545 O5 H5B O6A 0.79(4) 1.99(4) 2.771(12) 171(3) 3_666 O5 H5B O7 0.79(4) 2.04(4) 2.796(3) 160(3) 3_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.334 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.058