# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H38 Cd3 F12 N2 O20' _chemical_formula_weight 1383.88 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8606(15) _cell_length_b 11.6737(17) _cell_length_c 12.5124(18) _cell_angle_alpha 66.930(2) _cell_angle_beta 74.602(3) _cell_angle_gamma 65.787(2) _cell_volume 1199.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5694 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.27 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.442 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7056 _exptl_absorpt_correction_T_max 0.7236 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 6350 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4072 _reflns_number_gt 3740 _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^)+(0.1068P)^2^+3.6364P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4072 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.040 _refine_ls_shift/su_mean 0.001 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 Cd1 Cd 0.58309(4) 0.12632(3) 0.35238(3) 0.02763(18) Uani 1 1 d . . . Cd2 Cd 1.0000 0.0000 0.0000 0.0366(2) Uani 1 2 d S . . C1 C 0.6754(6) 0.3398(5) 0.3822(5) 0.0341(12) Uani 1 1 d . . . C2 C 0.6512(6) 0.4778(5) 0.3809(4) 0.0288(11) Uani 1 1 d . . . C3 C 0.5427(6) 0.5910(5) 0.3213(5) 0.0306(11) Uani 1 1 d . . . C4 C 0.5290(6) 0.7169(5) 0.3141(5) 0.0324(11) Uani 1 1 d . . . C5 C 0.6189(6) 0.7369(5) 0.3688(4) 0.0303(11) Uani 1 1 d . . . C6 C 0.7221(7) 0.6239(6) 0.4309(5) 0.0371(12) Uani 1 1 d . . . C7 C 0.7382(7) 0.4992(6) 0.4364(5) 0.0370(12) Uani 1 1 d . . . C8 C 0.6031(6) 0.8752(5) 0.3617(5) 0.0346(12) Uani 1 1 d . . . C9 C 0.7360(6) 0.2376(5) 0.0696(5) 0.0304(11) Uani 1 1 d . . . C10 C 0.6125(6) 0.3739(5) 0.0348(4) 0.0258(10) Uani 1 1 d . . . C11 C 0.4897(6) 0.3922(5) -0.0110(5) 0.0313(11) Uani 1 1 d . . . C12 C 0.6201(6) 0.4848(5) 0.0453(5) 0.0299(11) Uani 1 1 d . . . C13 C 0.2936(7) 0.3518(6) 0.2564(6) 0.0451(14) Uani 1 1 d . . . H13 H 0.3281 0.4013 0.2787 0.054 Uiso 1 1 calc R . . C14 C 0.0706(12) 0.5441(11) 0.2124(12) 0.115(5) Uani 1 1 d . . . H14A H 0.1215 0.5800 0.2399 0.173 Uiso 1 1 calc R . . H14B H -0.0231 0.5453 0.2609 0.173 Uiso 1 1 calc R . . H14C H 0.0524 0.5968 0.1330 0.173 Uiso 1 1 calc R . . C15 C 0.1039(11) 0.3356(11) 0.1819(10) 0.091(3) Uani 1 1 d . . . H15A H 0.1817 0.2540 0.1770 0.136 Uiso 1 1 calc R . . H15B H 0.0692 0.3875 0.1067 0.136 Uiso 1 1 calc R . . H15C H 0.0221 0.3166 0.2385 0.136 Uiso 1 1 calc R . . C16 C 0.8390(9) -0.0651(8) 0.5330(7) 0.063(2) Uani 1 1 d . . . H16A H 0.7527 -0.0385 0.5872 0.095 Uiso 1 1 calc R . . H16B H 0.9256 -0.0660 0.5551 0.095 Uiso 1 1 calc R . . H16C H 0.8546 -0.1523 0.5341 0.095 Uiso 1 1 calc R . . C17 C 0.9253(10) 0.1566(8) -0.2764(7) 0.073(3) Uani 1 1 d . . . H17A H 0.8425 0.2149 -0.2404 0.109 Uiso 1 1 calc R . . H17B H 0.8919 0.1435 -0.3348 0.109 Uiso 1 1 calc R . . H17C H 1.0022 0.1953 -0.3126 0.109 Uiso 1 1 calc R . . C18 C 1.278(2) 0.088(2) -0.0043(12) 0.162(9) Uani 1 1 d . . . H18A H 1.3696 0.0956 -0.0519 0.242 Uiso 1 1 calc R . . H18B H 1.2983 0.0046 0.0574 0.242 Uiso 1 1 calc R . . H18C H 1.2313 0.1590 0.0289 0.242 Uiso 1 1 calc R . . F1 F 0.4467(4) 0.5828(3) 0.2677(4) 0.0504(9) Uani 1 1 d . . . F2 F 0.4242(5) 0.8228(3) 0.2520(4) 0.0600(11) Uani 1 1 d . . . F3 F 0.8117(5) 0.6364(4) 0.4871(4) 0.0628(12) Uani 1 1 d . . . F4 F 0.8433(5) 0.3963(4) 0.4993(4) 0.0668(13) Uani 1 1 d . . . F5 F 0.4740(4) 0.2886(3) -0.0216(4) 0.0482(9) Uani 1 1 d . . . F6 F 0.7389(4) 0.4725(4) 0.0886(4) 0.0503(9) Uani 1 1 d . . . N1 N 0.1623(7) 0.4095(6) 0.2173(6) 0.0602(16) Uani 1 1 d . . . O1 O 0.5665(4) 0.3183(4) 0.3710(4) 0.0382(9) Uani 1 1 d . . . O2 O 0.8062(6) 0.2607(5) 0.3882(6) 0.0678(16) Uani 1 1 d . . . O3 O 0.6453(7) 0.9484(5) 0.2680(4) 0.0630(15) Uani 1 1 d . . . O4 O 0.5504(6) 0.9087(4) 0.4490(4) 0.0526(12) Uani 1 1 d . . . O5 O 0.7441(4) 0.1773(4) 0.1761(3) 0.0399(10) Uani 1 1 d . . . O6 O 0.8198(5) 0.2020(4) -0.0129(4) 0.0535(13) Uani 1 1 d . . . O7 O 0.3741(5) 0.2347(5) 0.2653(4) 0.0483(11) Uani 1 1 d . . . O8 O 0.8149(4) 0.0280(4) 0.4157(4) 0.0407(9) Uani 1 1 d . . . H8 H 0.8160 0.0937 0.4244 0.061 Uiso 1 1 d R . . O9 O 0.9842(5) 0.0312(5) -0.1891(4) 0.0538(12) Uani 1 1 d . . . H9 H 1.0712 0.0179 -0.2203 0.081 Uiso 1 1 d R . . O10 O 1.1836(6) 0.0964(6) -0.0715(5) 0.0639(14) Uani 1 1 d . . . H10 H 1.1242 0.1725 -0.0815 0.096 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0308(3) 0.0174(2) 0.0361(3) -0.01013(17) -0.00212(16) -0.00962(17) Cd2 0.0328(3) 0.0241(3) 0.0355(3) -0.0084(2) -0.0019(2) 0.0042(2) C1 0.041(3) 0.018(2) 0.043(3) -0.010(2) -0.002(2) -0.012(2) C2 0.041(3) 0.018(2) 0.032(2) -0.011(2) -0.001(2) -0.014(2) C3 0.037(3) 0.025(3) 0.037(3) -0.014(2) -0.007(2) -0.013(2) C4 0.037(3) 0.020(2) 0.042(3) -0.013(2) -0.009(2) -0.006(2) C5 0.040(3) 0.026(3) 0.031(3) -0.016(2) 0.006(2) -0.017(2) C6 0.046(3) 0.036(3) 0.040(3) -0.017(2) -0.007(2) -0.019(3) C7 0.045(3) 0.027(3) 0.037(3) -0.006(2) -0.008(2) -0.012(2) C8 0.037(3) 0.026(3) 0.046(3) -0.017(2) 0.003(2) -0.015(2) C9 0.025(2) 0.019(2) 0.037(3) -0.009(2) -0.002(2) 0.001(2) C10 0.030(2) 0.013(2) 0.029(2) -0.0069(19) -0.0008(19) -0.0034(19) C11 0.032(3) 0.020(2) 0.037(3) -0.010(2) -0.004(2) -0.003(2) C12 0.030(3) 0.022(2) 0.038(3) -0.011(2) -0.005(2) -0.008(2) C13 0.048(4) 0.039(3) 0.047(3) -0.014(3) 0.004(3) -0.020(3) C14 0.063(6) 0.066(6) 0.133(10) -0.004(6) 0.010(6) 0.016(5) C15 0.062(5) 0.095(7) 0.103(7) 0.006(6) -0.039(5) -0.035(5) C16 0.051(4) 0.062(5) 0.060(4) 0.006(4) -0.022(3) -0.019(4) C17 0.069(5) 0.063(5) 0.051(4) -0.015(4) -0.024(4) 0.016(4) C18 0.201(17) 0.30(3) 0.097(9) -0.087(13) 0.032(10) -0.204(19) F1 0.056(2) 0.0327(18) 0.075(3) -0.0176(17) -0.0340(19) -0.0112(16) F2 0.067(3) 0.0231(18) 0.092(3) -0.0112(19) -0.044(2) -0.0036(17) F3 0.085(3) 0.046(2) 0.085(3) -0.029(2) -0.040(2) -0.023(2) F4 0.083(3) 0.032(2) 0.090(3) -0.007(2) -0.058(3) -0.008(2) F5 0.054(2) 0.0226(16) 0.075(3) -0.0193(16) -0.0190(19) -0.0092(15) F6 0.0395(19) 0.039(2) 0.074(2) -0.0141(18) -0.0294(18) -0.0054(15) N1 0.042(3) 0.052(4) 0.057(3) -0.002(3) 0.000(3) -0.007(3) O1 0.038(2) 0.0247(19) 0.061(3) -0.0217(18) 0.0014(18) -0.0174(16) O2 0.042(3) 0.035(3) 0.128(5) -0.032(3) -0.023(3) -0.002(2) O3 0.107(4) 0.038(3) 0.057(3) -0.022(2) 0.016(3) -0.047(3) O4 0.078(3) 0.041(2) 0.055(3) -0.035(2) 0.024(2) -0.037(2) O5 0.034(2) 0.029(2) 0.033(2) -0.0006(16) 0.0002(16) 0.0008(16) O6 0.054(3) 0.034(2) 0.037(2) -0.0136(18) -0.0007(19) 0.018(2) O7 0.039(2) 0.047(3) 0.053(3) -0.009(2) -0.0149(19) -0.009(2) O8 0.040(2) 0.026(2) 0.056(2) -0.0066(18) -0.0141(18) -0.0125(17) O9 0.041(2) 0.049(3) 0.043(2) -0.015(2) -0.0061(19) 0.012(2) O10 0.065(3) 0.066(3) 0.067(3) -0.033(3) 0.015(3) -0.032(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O7 2.238(4) . ? Cd1 O1 2.278(4) . ? Cd1 O8 2.295(4) . ? Cd1 O5 2.372(4) . ? Cd1 O4 2.446(4) 2_666 ? Cd1 O4 2.466(4) 1_545 ? Cd1 O3 2.476(5) 1_545 ? Cd2 O6 2.272(4) . ? Cd2 O6 2.272(4) 2_755 ? Cd2 O9 2.286(5) 2_755 ? Cd2 O9 2.286(5) . ? Cd2 O10 2.317(5) 2_755 ? Cd2 O10 2.317(5) . ? C1 O2 1.242(8) . ? C1 O1 1.251(7) . ? C1 C2 1.523(7) . ? C2 C7 1.380(8) . ? C2 C3 1.392(8) . ? C3 F1 1.347(6) . ? C3 C4 1.388(7) . ? C4 F2 1.351(6) . ? C4 C5 1.388(8) . ? C5 C6 1.376(8) . ? C5 C8 1.526(7) . ? C6 F3 1.346(7) . ? C6 C7 1.374(8) . ? C7 F4 1.345(7) . ? C8 O4 1.218(7) . ? C8 O3 1.236(7) . ? C9 O6 1.234(7) . ? C9 O5 1.247(7) . ? C9 C10 1.534(6) . ? C10 C11 1.379(8) . ? C10 C12 1.384(7) . ? C11 F5 1.340(6) . ? C11 C12 1.381(7) 2_665 ? C12 F6 1.351(6) . ? C12 C11 1.381(7) 2_665 ? C13 O7 1.245(8) . ? C13 N1 1.315(9) . ? C13 H13 0.9300 . ? C14 N1 1.442(12) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N1 1.455(13) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O8 1.455(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O9 1.436(8) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O10 1.362(14) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O3 Cd1 2.476(5) 1_565 ? O4 Cd1 2.446(4) 2_666 ? O4 Cd1 2.466(4) 1_565 ? O8 H8 0.8200 . ? O9 H9 0.8199 . ? O10 H10 0.8199 . ? 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 O7 Cd1 O1 89.79(16) . . ? O7 Cd1 O8 171.67(16) . . ? O1 Cd1 O8 88.74(14) . . ? O7 Cd1 O5 94.27(15) . . ? O1 Cd1 O5 86.93(15) . . ? O8 Cd1 O5 77.46(15) . . ? O7 Cd1 O4 94.42(18) . 2_666 ? O1 Cd1 O4 83.27(14) . 2_666 ? O8 Cd1 O4 93.55(17) . 2_666 ? O5 Cd1 O4 166.86(16) . 2_666 ? O7 Cd1 O4 98.03(18) . 1_545 ? O1 Cd1 O4 147.30(15) . 1_545 ? O8 Cd1 O4 87.58(16) . 1_545 ? O5 Cd1 O4 123.74(14) . 1_545 ? O4 Cd1 O4 64.57(15) 2_666 1_545 ? O7 Cd1 O3 89.0(2) . 1_545 ? O1 Cd1 O3 160.85(16) . 1_545 ? O8 Cd1 O3 89.68(19) . 1_545 ? O5 Cd1 O3 74.11(16) . 1_545 ? O4 Cd1 O3 115.88(14) 2_666 1_545 ? O4 Cd1 O3 51.61(15) 1_545 1_545 ? O6 Cd2 O6 180.0(3) . 2_755 ? O6 Cd2 O9 90.18(16) . 2_755 ? O6 Cd2 O9 89.82(16) 2_755 2_755 ? O6 Cd2 O9 89.82(16) . . ? O6 Cd2 O9 90.18(16) 2_755 . ? O9 Cd2 O9 180.0(3) 2_755 . ? O6 Cd2 O10 89.6(2) . 2_755 ? O6 Cd2 O10 90.4(2) 2_755 2_755 ? O9 Cd2 O10 88.1(2) 2_755 2_755 ? O9 Cd2 O10 91.9(2) . 2_755 ? O6 Cd2 O10 90.4(2) . . ? O6 Cd2 O10 89.6(2) 2_755 . ? O9 Cd2 O10 91.9(2) 2_755 . ? O9 Cd2 O10 88.1(2) . . ? O10 Cd2 O10 180.0(2) 2_755 . ? O2 C1 O1 126.1(5) . . ? O2 C1 C2 115.4(5) . . ? O1 C1 C2 118.3(5) . . ? C7 C2 C3 115.7(5) . . ? C7 C2 C1 122.1(5) . . ? C3 C2 C1 122.2(5) . . ? F1 C3 C4 117.2(5) . . ? F1 C3 C2 121.3(5) . . ? C4 C3 C2 121.5(5) . . ? F2 C4 C3 118.6(5) . . ? F2 C4 C5 119.4(5) . . ? C3 C4 C5 122.1(5) . . ? C6 C5 C4 115.7(5) . . ? C6 C5 C8 122.2(5) . . ? C4 C5 C8 122.1(5) . . ? F3 C6 C7 118.9(5) . . ? F3 C6 C5 118.6(5) . . ? C7 C6 C5 122.4(5) . . ? F4 C7 C6 117.0(5) . . ? F4 C7 C2 120.5(5) . . ? C6 C7 C2 122.5(5) . . ? O4 C8 O3 122.5(5) . . ? O4 C8 C5 118.6(5) . . ? O3 C8 C5 118.8(5) . . ? O6 C9 O5 127.2(5) . . ? O6 C9 C10 115.2(5) . . ? O5 C9 C10 117.5(4) . . ? C11 C10 C12 116.8(5) . . ? C11 C10 C9 121.3(5) . . ? C12 C10 C9 121.9(5) . . ? F5 C11 C10 119.9(5) . . ? F5 C11 C12 118.5(5) . 2_665 ? C10 C11 C12 121.7(5) . 2_665 ? F6 C12 C11 119.3(5) . 2_665 ? F6 C12 C10 119.1(5) . . ? C11 C12 C10 121.6(5) 2_665 . ? O7 C13 N1 123.7(7) . . ? O7 C13 H13 118.2 . . ? N1 C13 H13 118.2 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O8 C16 H16A 109.5 . . ? O8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O9 C17 H17A 109.5 . . ? O9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O10 C18 H18A 109.5 . . ? O10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 N1 C14 121.7(9) . . ? C13 N1 C15 120.0(7) . . ? C14 N1 C15 118.3(9) . . ? C1 O1 Cd1 124.0(3) . . ? C8 O3 Cd1 92.4(4) . 1_565 ? C8 O4 Cd1 150.7(4) . 2_666 ? C8 O4 Cd1 93.4(3) . 1_565 ? Cd1 O4 Cd1 115.43(15) 2_666 1_565 ? C9 O5 Cd1 139.1(4) . . ? C9 O6 Cd2 126.2(4) . . ? C13 O7 Cd1 124.3(5) . . ? C16 O8 Cd1 121.9(4) . . ? C16 O8 H8 99.4 . . ? Cd1 O8 H8 96.2 . . ? C17 O9 Cd2 125.9(5) . . ? C17 O9 H9 94.5 . . ? Cd2 O9 H9 103.6 . . ? C18 O10 Cd2 124.0(7) . . ? C18 O10 H10 102.2 . . ? Cd2 O10 H10 94.6 . . ? 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 O2 C1 C2 C7 -29.9(8) . . . . ? O1 C1 C2 C7 153.7(6) . . . . ? O2 C1 C2 C3 148.4(6) . . . . ? O1 C1 C2 C3 -28.0(8) . . . . ? C7 C2 C3 F1 -177.3(5) . . . . ? C1 C2 C3 F1 4.4(8) . . . . ? C7 C2 C3 C4 3.0(8) . . . . ? C1 C2 C3 C4 -175.4(5) . . . . ? F1 C3 C4 F2 -1.7(8) . . . . ? C2 C3 C4 F2 178.1(5) . . . . ? F1 C3 C4 C5 178.1(5) . . . . ? C2 C3 C4 C5 -2.1(9) . . . . ? F2 C4 C5 C6 179.6(5) . . . . ? C3 C4 C5 C6 -0.2(8) . . . . ? F2 C4 C5 C8 0.3(8) . . . . ? C3 C4 C5 C8 -179.5(5) . . . . ? C4 C5 C6 F3 -179.3(5) . . . . ? C8 C5 C6 F3 0.0(8) . . . . ? C4 C5 C6 C7 1.6(8) . . . . ? C8 C5 C6 C7 -179.1(5) . . . . ? F3 C6 C7 F4 0.5(9) . . . . ? C5 C6 C7 F4 179.7(6) . . . . ? F3 C6 C7 C2 -179.8(5) . . . . ? C5 C6 C7 C2 -0.6(9) . . . . ? C3 C2 C7 F4 178.0(5) . . . . ? C1 C2 C7 F4 -3.6(9) . . . . ? C3 C2 C7 C6 -1.7(8) . . . . ? C1 C2 C7 C6 176.7(6) . . . . ? C6 C5 C8 O4 -70.4(8) . . . . ? C4 C5 C8 O4 108.9(7) . . . . ? C6 C5 C8 O3 109.1(7) . . . . ? C4 C5 C8 O3 -71.7(8) . . . . ? O6 C9 C10 C11 73.7(7) . . . . ? O5 C9 C10 C11 -108.5(6) . . . . ? O6 C9 C10 C12 -104.9(6) . . . . ? O5 C9 C10 C12 72.9(7) . . . . ? C12 C10 C11 F5 -178.8(5) . . . . ? C9 C10 C11 F5 2.5(8) . . . . ? C12 C10 C11 C12 0.3(9) . . . 2_665 ? C9 C10 C11 C12 -178.4(5) . . . 2_665 ? C11 C10 C12 F6 -179.4(5) . . . . ? C9 C10 C12 F6 -0.8(8) . . . . ? C11 C10 C12 C11 -0.3(9) . . . 2_665 ? C9 C10 C12 C11 178.4(5) . . . 2_665 ? O7 C13 N1 C14 177.8(8) . . . . ? O7 C13 N1 C15 0.1(11) . . . . ? O2 C1 O1 Cd1 -2.3(9) . . . . ? C2 C1 O1 Cd1 173.7(3) . . . . ? O7 Cd1 O1 C1 -156.9(5) . . . . ? O8 Cd1 O1 C1 14.9(5) . . . . ? O5 Cd1 O1 C1 -62.6(5) . . . . ? O4 Cd1 O1 C1 108.6(5) 2_666 . . . ? O4 Cd1 O1 C1 98.5(5) 1_545 . . . ? O3 Cd1 O1 C1 -70.5(8) 1_545 . . . ? O4 C8 O3 Cd1 1.7(7) . . . 1_565 ? C5 C8 O3 Cd1 -177.8(5) . . . 1_565 ? O3 C8 O4 Cd1 167.8(7) . . . 2_666 ? C5 C8 O4 Cd1 -12.8(13) . . . 2_666 ? O3 C8 O4 Cd1 -1.7(7) . . . 1_565 ? C5 C8 O4 Cd1 177.8(5) . . . 1_565 ? O6 C9 O5 Cd1 -137.9(6) . . . . ? C10 C9 O5 Cd1 44.5(8) . . . . ? O7 Cd1 O5 C9 -0.7(6) . . . . ? O1 Cd1 O5 C9 -90.3(6) . . . . ? O8 Cd1 O5 C9 -179.7(6) . . . . ? O4 Cd1 O5 C9 -132.0(7) 2_666 . . . ? O4 Cd1 O5 C9 101.9(6) 1_545 . . . ? O3 Cd1 O5 C9 87.0(6) 1_545 . . . ? O5 C9 O6 Cd2 9.1(10) . . . . ? C10 C9 O6 Cd2 -173.3(4) . . . . ? O6 Cd2 O6 C9 157(13) 2_755 . . . ? O9 Cd2 O6 C9 -24.1(6) 2_755 . . . ? O9 Cd2 O6 C9 155.9(6) . . . . ? O10 Cd2 O6 C9 64.1(6) 2_755 . . . ? O10 Cd2 O6 C9 -115.9(6) . . . . ? N1 C13 O7 Cd1 -171.8(5) . . . . ? O1 Cd1 O7 C13 -7.1(5) . . . . ? O8 Cd1 O7 C13 -87.0(12) . . . . ? O5 Cd1 O7 C13 -94.0(5) . . . . ? O4 Cd1 O7 C13 76.1(5) 2_666 . . . ? O4 Cd1 O7 C13 141.0(5) 1_545 . . . ? O3 Cd1 O7 C13 -168.0(5) 1_545 . . . ? O7 Cd1 O8 C16 -174.8(11) . . . . ? O1 Cd1 O8 C16 105.2(5) . . . . ? O5 Cd1 O8 C16 -167.6(6) . . . . ? O4 Cd1 O8 C16 22.1(5) 2_666 . . . ? O4 Cd1 O8 C16 -42.3(5) 1_545 . . . ? O3 Cd1 O8 C16 -93.8(5) 1_545 . . . ? O6 Cd2 O9 C17 21.0(6) . . . . ? O6 Cd2 O9 C17 -159.0(6) 2_755 . . . ? O9 Cd2 O9 C17 144(55) 2_755 . . . ? O10 Cd2 O9 C17 110.6(6) 2_755 . . . ? O10 Cd2 O9 C17 -69.4(6) . . . . ? O6 Cd2 O10 C18 105.4(12) . . . . ? O6 Cd2 O10 C18 -74.6(12) 2_755 . . . ? O9 Cd2 O10 C18 15.2(12) 2_755 . . . ? O9 Cd2 O10 C18 -164.8(12) . . . . ? O10 Cd2 O10 C18 -147(100) 2_755 . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.981 _refine_diff_density_min -1.072 _refine_diff_density_rms 0.248 _database_code_depnum_ccdc_archive 'CCDC 943280' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Cd F4 N2 O8' _chemical_formula_weight 530.70 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.4767(7) _cell_length_b 10.4619(13) _cell_length_c 17.4891(19) _cell_angle_alpha 90.00 _cell_angle_beta 106.381(4) _cell_angle_gamma 90.00 _cell_volume 961.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4539 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.95 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7586 _exptl_absorpt_correction_T_max 0.7754 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5123 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1682 _reflns_number_gt 1590 _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^)+(0.0377P)^2^+1.1697P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1682 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Cd1 Cd 0.0000 0.0000 0.0000 0.03351(13) Uani 1 2 d S . . C1 C 0.1390(5) 0.2857(2) -0.02439(17) 0.0318(6) Uani 1 1 d . . . C2 C 0.3275(5) 0.3964(2) -0.01136(16) 0.0295(6) Uani 1 1 d . . . C3 C 0.4276(6) 0.4510(3) 0.06237(17) 0.0342(6) Uani 1 1 d . . . C4 C 0.5962(6) 0.5522(3) 0.07359(17) 0.0340(6) Uani 1 1 d . . . C5 C -0.0771(7) 0.1666(3) 0.1433(2) 0.0492(8) Uani 1 1 d . . . H5 H 0.0363 0.2184 0.1268 0.059 Uiso 1 1 calc R . . C6 C -0.0592(9) 0.3261(4) 0.2445(2) 0.0646(10) Uani 1 1 d . . . H6A H 0.0243 0.3076 0.2995 0.097 Uiso 1 1 calc R . . H6B H -0.1977 0.3841 0.2412 0.097 Uiso 1 1 calc R . . H6C H 0.0601 0.3645 0.2204 0.097 Uiso 1 1 calc R . . C7 C -0.3367(8) 0.1351(4) 0.2317(3) 0.0652(10) Uani 1 1 d . . . H7A H -0.4072 0.0680 0.1946 0.098 Uiso 1 1 calc R . . H7B H -0.4709 0.1903 0.2370 0.098 Uiso 1 1 calc R . . H7C H -0.2516 0.0987 0.2826 0.098 Uiso 1 1 calc R . . F1 F 0.3557(4) 0.40742(19) 0.12517(11) 0.0544(5) Uani 1 1 d . . . F2 F 0.6831(4) 0.60303(19) 0.14714(11) 0.0554(5) Uani 1 1 d . . . N1 N -0.1569(5) 0.2078(3) 0.20280(16) 0.0445(6) Uani 1 1 d . . . O1 O 0.2312(4) 0.17944(19) 0.00060(15) 0.0502(6) Uani 1 1 d . . . O2 O -0.0835(5) 0.3099(2) -0.0585(2) 0.0721(9) Uani 1 1 d . . . O3 O -0.1393(5) 0.0646(2) 0.10716(15) 0.0538(6) Uani 1 1 d . . . O4 O 0.3598(4) -0.0938(2) 0.08345(15) 0.0533(6) Uani 1 1 d . . . H4A H 0.3206 -0.1693 0.0845 0.080 Uiso 1 1 d R . . H4B H 0.4781 -0.0715 0.0663 0.080 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03260(19) 0.02057(18) 0.0509(2) 0.00064(11) 0.01755(14) -0.00551(10) C1 0.0328(14) 0.0209(13) 0.0454(15) -0.0021(11) 0.0170(12) -0.0053(11) C2 0.0296(13) 0.0171(12) 0.0432(15) 0.0008(11) 0.0128(11) -0.0037(10) C3 0.0380(15) 0.0266(14) 0.0426(15) 0.0037(12) 0.0186(12) -0.0063(12) C4 0.0391(15) 0.0250(14) 0.0386(15) -0.0045(12) 0.0123(12) -0.0075(12) C5 0.0526(19) 0.0457(19) 0.0552(19) 0.0022(16) 0.0247(16) -0.0072(16) C6 0.083(3) 0.047(2) 0.063(2) -0.0068(18) 0.019(2) -0.008(2) C7 0.071(3) 0.064(2) 0.073(3) -0.007(2) 0.041(2) -0.010(2) F1 0.0740(13) 0.0519(11) 0.0449(10) -0.0022(8) 0.0292(9) -0.0315(10) F2 0.0722(13) 0.0556(12) 0.0408(10) -0.0148(8) 0.0201(9) -0.0340(10) N1 0.0504(16) 0.0392(14) 0.0462(14) 0.0013(12) 0.0176(12) 0.0002(12) O1 0.0362(11) 0.0214(10) 0.0896(17) 0.0111(10) 0.0120(11) -0.0075(9) O2 0.0338(13) 0.0356(13) 0.133(3) 0.0105(14) 0.0006(14) -0.0066(10) O3 0.0632(15) 0.0455(14) 0.0610(14) -0.0048(12) 0.0312(12) -0.0037(12) O4 0.0363(11) 0.0485(14) 0.0737(16) 0.0140(12) 0.0135(11) -0.0059(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O1 2.263(2) 3 ? Cd1 O1 2.263(2) . ? Cd1 O4 2.314(2) . ? Cd1 O4 2.314(2) 3 ? Cd1 O3 2.315(2) . ? Cd1 O3 2.315(2) 3 ? C1 O2 1.223(4) . ? C1 O1 1.248(3) . ? C1 C2 1.525(4) . ? C2 C3 1.375(4) . ? C2 C4 1.380(4) 3_665 ? C3 F1 1.347(3) . ? C3 C4 1.382(4) . ? C4 F2 1.349(3) . ? C4 C2 1.380(4) 3_665 ? C5 O3 1.238(4) . ? C5 N1 1.310(4) . ? C5 H5 0.9300 . ? C6 N1 1.459(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N1 1.444(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O4 H4A 0.8200 . ? O4 H4B 0.8199 . ? 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 Cd1 O1 180.00(14) 3 . ? O1 Cd1 O4 91.55(8) 3 . ? O1 Cd1 O4 88.45(8) . . ? O1 Cd1 O4 88.45(8) 3 3 ? O1 Cd1 O4 91.55(8) . 3 ? O4 Cd1 O4 180.00(15) . 3 ? O1 Cd1 O3 86.22(9) 3 . ? O1 Cd1 O3 93.78(9) . . ? O4 Cd1 O3 91.70(9) . . ? O4 Cd1 O3 88.30(9) 3 . ? O1 Cd1 O3 93.78(9) 3 3 ? O1 Cd1 O3 86.22(9) . 3 ? O4 Cd1 O3 88.30(9) . 3 ? O4 Cd1 O3 91.70(9) 3 3 ? O3 Cd1 O3 180.00(10) . 3 ? O2 C1 O1 127.2(3) . . ? O2 C1 C2 117.1(2) . . ? O1 C1 C2 115.7(2) . . ? C3 C2 C4 116.6(2) . 3_665 ? C3 C2 C1 122.0(2) . . ? C4 C2 C1 121.4(2) 3_665 . ? F1 C3 C2 119.5(2) . . ? F1 C3 C4 118.7(3) . . ? C2 C3 C4 121.7(3) . . ? F2 C4 C2 119.6(2) . 3_665 ? F2 C4 C3 118.7(2) . . ? C2 C4 C3 121.7(3) 3_665 . ? O3 C5 N1 125.8(3) . . ? O3 C5 H5 117.1 . . ? N1 C5 H5 117.1 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 N1 C7 121.2(3) . . ? C5 N1 C6 121.3(3) . . ? C7 N1 C6 117.5(3) . . ? C1 O1 Cd1 124.54(18) . . ? C5 O3 Cd1 124.0(2) . . ? Cd1 O4 H4A 103.9 . . ? Cd1 O4 H4B 105.6 . . ? H4A O4 H4B 121.4 . . ? 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 O2 C1 C2 C3 106.1(4) . . . . ? O1 C1 C2 C3 -74.6(4) . . . . ? O2 C1 C2 C4 -73.1(4) . . . 3_665 ? O1 C1 C2 C4 106.2(3) . . . 3_665 ? C4 C2 C3 F1 178.3(3) 3_665 . . . ? C1 C2 C3 F1 -1.0(4) . . . . ? C4 C2 C3 C4 -0.1(5) 3_665 . . . ? C1 C2 C3 C4 -179.3(3) . . . . ? F1 C3 C4 F2 0.3(4) . . . . ? C2 C3 C4 F2 178.6(3) . . . . ? F1 C3 C4 C2 -178.3(3) . . . 3_665 ? C2 C3 C4 C2 0.1(5) . . . 3_665 ? O3 C5 N1 C7 -1.1(6) . . . . ? O3 C5 N1 C6 176.2(4) . . . . ? O2 C1 O1 Cd1 -6.2(5) . . . . ? C2 C1 O1 Cd1 174.62(18) . . . . ? O1 Cd1 O1 C1 111(100) 3 . . . ? O4 Cd1 O1 C1 -167.0(3) . . . . ? O4 Cd1 O1 C1 13.0(3) 3 . . . ? O3 Cd1 O1 C1 -75.4(3) . . . . ? O3 Cd1 O1 C1 104.6(3) 3 . . . ? N1 C5 O3 Cd1 178.1(3) . . . . ? O1 Cd1 O3 C5 178.9(3) 3 . . . ? O1 Cd1 O3 C5 -1.1(3) . . . . ? O4 Cd1 O3 C5 87.5(3) . . . . ? O4 Cd1 O3 C5 -92.5(3) 3 . . . ? O3 Cd1 O3 C5 -28(100) 3 . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.374 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 943281' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H32 Cl12 N4 Na2 O17 Zn2' _chemical_formula_weight 1406.79 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.597(4) _cell_length_b 17.566(3) _cell_length_c 19.258(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.427(2) _cell_angle_gamma 90.00 _cell_volume 5633.7(19) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9980 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.57 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2816 _exptl_absorpt_coefficient_mu 1.503 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.761 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 23765 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.62 _reflns_number_total 6527 _reflns_number_gt 5009 _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^)+(0.0897P)^2^+48.3315P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6527 _refine_ls_number_parameters 343 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1970 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.053 _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 Zn1 Zn 0.24177(3) 0.96705(3) 0.41158(3) 0.03043(18) Uani 1 1 d . . . Na1 Na 0.08223(13) 0.89932(13) 0.24256(12) 0.0389(5) Uani 1 1 d U . . C1 C 0.2075(3) 1.0476(3) 0.2739(3) 0.0397(12) Uani 1 1 d . . . C2 C 0.2161(3) 1.1211(3) 0.2361(3) 0.0335(10) Uani 1 1 d . . . C3 C 0.2523(3) 1.1222(3) 0.1863(3) 0.0332(10) Uani 1 1 d . . . C4 C 0.2573(3) 1.1897(3) 0.1505(3) 0.0304(10) Uani 1 1 d . . . C5 C 0.2270(3) 1.2568(3) 0.1643(3) 0.0307(10) Uani 1 1 d . . . C6 C 0.1917(3) 1.2558(3) 0.2152(3) 0.0333(10) Uani 1 1 d . . . C7 C 0.1860(3) 1.1886(3) 0.2500(3) 0.0337(11) Uani 1 1 d . . . C8 C 0.2242(4) 1.3290(3) 0.1202(4) 0.0477(14) Uani 1 1 d . . . C9 C 0.0856(3) 0.9706(3) 0.4067(3) 0.0369(12) Uani 1 1 d . . . C10 C 0.0389(3) 0.9859(4) 0.4539(3) 0.0370(12) Uani 1 1 d . . . C11 C 0.0042(3) 1.0555(3) 0.4504(3) 0.0353(11) Uani 1 1 d . . . C12 C 0.0349(3) 0.9292(3) 0.5028(3) 0.0351(11) Uani 1 1 d . . . C13 C 0.4029(5) 0.9768(5) 0.5422(5) 0.073(2) Uani 1 1 d U . . H13 H 0.4105 0.9271 0.5302 0.088 Uiso 1 1 calc R . . C14 C 0.5449(6) 0.9782(6) 0.6339(7) 0.0965(18) Uani 1 1 d U . . H14A H 0.5635 0.9821 0.6890 0.145 Uiso 1 1 calc R . . H14B H 0.5819 1.0037 0.6195 0.145 Uiso 1 1 calc R . . H14C H 0.5412 0.9255 0.6194 0.145 Uiso 1 1 calc R . . C15 C 0.4535(6) 1.0880(6) 0.6222(6) 0.0939(18) Uani 1 1 d U . . H15A H 0.3973 1.1001 0.5986 0.141 Uiso 1 1 calc R . . H15B H 0.4821 1.1265 0.6091 0.141 Uiso 1 1 calc R . . H15C H 0.4732 1.0861 0.6775 0.141 Uiso 1 1 calc R . . C16 C 0.1481(4) 0.8518(4) 0.1226(4) 0.0501(15) Uani 1 1 d . . . H16 H 0.1649 0.9022 0.1317 0.060 Uiso 1 1 calc R . . C17 C 0.2177(5) 0.8439(5) 0.0417(4) 0.0619(18) Uani 1 1 d . . . H17A H 0.2245 0.8974 0.0526 0.093 Uiso 1 1 calc R . . H17B H 0.1920 0.8360 -0.0134 0.093 Uiso 1 1 calc R . . H17C H 0.2692 0.8193 0.0638 0.093 Uiso 1 1 calc R . . C18 C 0.1416(5) 0.7335(4) 0.0564(5) 0.069(2) Uani 1 1 d . . . H18A H 0.1078 0.7202 0.0804 0.103 Uiso 1 1 calc R . . H18B H 0.1874 0.7004 0.0751 0.103 Uiso 1 1 calc R . . H18C H 0.1119 0.7281 0.0012 0.103 Uiso 1 1 calc R . . C19 C 0.0082(12) 0.7265(11) 0.2264(11) 0.081(5) Uani 0.50 1 d PU . . H19A H 0.0081 0.6848 0.2586 0.121 Uiso 0.50 1 d PR . . H19B H 0.0589 0.7269 0.2244 0.121 Uiso 0.50 1 d PR . . H19C H -0.0336 0.7180 0.1749 0.121 Uiso 0.50 1 d PR . . Cl1 Cl 0.28872(11) 1.03804(9) 0.16722(10) 0.0534(4) Uani 1 1 d . . . Cl2 Cl 0.29776(9) 1.18929(9) 0.08503(8) 0.0429(3) Uani 1 1 d . . . Cl3 Cl 0.13822(9) 1.18726(9) 0.30962(9) 0.0480(4) Uani 1 1 d . . . Cl4 Cl 0.15728(10) 1.34085(9) 0.23503(10) 0.0542(4) Uani 1 1 d . . . Cl5 Cl 0.00874(8) 1.12574(10) 0.38933(8) 0.0466(4) Uani 1 1 d . . . Cl6 Cl 0.07727(9) 0.84092(10) 0.50480(9) 0.0499(4) Uani 1 1 d . . . N1 N 0.4655(5) 1.0137(5) 0.5940(5) 0.0928(17) Uani 1 1 d U . . N2 N 0.1681(3) 0.8117(3) 0.0751(3) 0.0505(13) Uani 1 1 d . . . O1 O 0.2589(3) 1.0421(2) 0.3452(2) 0.0475(10) Uani 1 1 d . . . O2 O 0.1545(3) 1.0035(3) 0.2354(3) 0.0502(10) Uani 1 1 d . . . O3 O 0.2870(3) 1.3688(2) 0.1452(3) 0.0594(13) Uani 1 1 d . . . O4 O 0.1623(4) 1.3451(4) 0.0637(4) 0.091(2) Uani 1 1 d . . . O5 O 0.0511(2) 0.9440(3) 0.3416(2) 0.0422(9) Uani 1 1 d . . . O6 O 0.1594(2) 0.9898(3) 0.4437(2) 0.0471(10) Uani 1 1 d . . . O7 O 0.3350(2) 1.0039(2) 0.5089(2) 0.0440(9) Uani 1 1 d . . . O8 O 0.1089(3) 0.8274(3) 0.1556(3) 0.0625(13) Uani 1 1 d . . . O9 O 0.0000 0.7961(5) 0.2500 0.0712(16) Uani 1 2 d SU . . H9 H 0.0159 0.8019 0.2968 0.107 Uiso 0.50 1 d PR . . 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 0.0295(3) 0.0354(3) 0.0302(3) 0.0051(2) 0.0167(2) 0.0073(2) Na1 0.0478(12) 0.0426(12) 0.0385(11) -0.0026(9) 0.0301(10) 0.0020(9) C1 0.047(3) 0.035(3) 0.043(3) 0.011(2) 0.026(3) 0.002(2) C2 0.034(2) 0.036(3) 0.028(2) 0.005(2) 0.0106(19) -0.003(2) C3 0.037(2) 0.033(3) 0.029(2) 0.003(2) 0.014(2) 0.001(2) C4 0.027(2) 0.034(3) 0.030(2) 0.0024(19) 0.0133(19) -0.0030(18) C5 0.028(2) 0.031(3) 0.030(2) 0.0009(19) 0.0108(19) -0.0068(18) C6 0.031(2) 0.031(3) 0.035(3) -0.004(2) 0.012(2) -0.0047(19) C7 0.030(2) 0.039(3) 0.031(3) -0.002(2) 0.013(2) -0.007(2) C8 0.064(4) 0.033(3) 0.060(4) 0.003(3) 0.041(3) -0.003(3) C9 0.035(2) 0.054(3) 0.029(3) 0.006(2) 0.021(2) 0.014(2) C10 0.027(2) 0.064(4) 0.023(2) 0.000(2) 0.0127(19) 0.012(2) C11 0.027(2) 0.059(3) 0.021(2) 0.006(2) 0.0112(18) 0.010(2) C12 0.027(2) 0.052(3) 0.026(2) 0.002(2) 0.0116(19) 0.015(2) C13 0.074(4) 0.064(5) 0.083(6) -0.005(4) 0.035(4) 0.018(3) C14 0.0944(19) 0.095(2) 0.097(2) -0.0016(10) 0.0399(11) 0.0005(10) C15 0.0923(19) 0.0928(19) 0.0940(19) -0.0019(10) 0.0392(11) 0.0000(10) C16 0.056(3) 0.048(4) 0.055(4) -0.009(3) 0.032(3) 0.005(3) C17 0.074(5) 0.075(5) 0.052(4) 0.004(3) 0.041(4) 0.009(4) C18 0.073(5) 0.058(4) 0.076(5) -0.022(4) 0.034(4) 0.002(4) C19 0.080(5) 0.080(5) 0.081(5) 0.0001(10) 0.036(2) -0.0003(10) Cl1 0.0754(10) 0.0389(8) 0.0615(10) 0.0100(7) 0.0445(9) 0.0144(7) Cl2 0.0511(7) 0.0487(8) 0.0389(7) 0.0068(6) 0.0291(6) -0.0004(6) Cl3 0.0545(8) 0.0573(9) 0.0468(8) -0.0002(6) 0.0357(7) -0.0043(7) Cl4 0.0675(10) 0.0386(8) 0.0674(10) -0.0006(7) 0.0397(8) 0.0076(7) Cl5 0.0443(7) 0.0632(9) 0.0370(7) 0.0142(6) 0.0225(6) 0.0117(6) Cl6 0.0452(7) 0.0617(9) 0.0451(8) 0.0082(7) 0.0220(6) 0.0272(7) N1 0.087(2) 0.091(2) 0.094(2) -0.0053(15) 0.0351(16) -0.0010(15) N2 0.051(3) 0.058(3) 0.047(3) -0.010(2) 0.026(2) 0.005(2) O1 0.053(2) 0.052(3) 0.038(2) 0.0151(18) 0.0208(19) 0.0019(19) O2 0.061(3) 0.042(2) 0.048(2) 0.0094(19) 0.025(2) -0.010(2) O3 0.093(3) 0.037(2) 0.072(3) -0.016(2) 0.059(3) -0.029(2) O4 0.086(4) 0.087(4) 0.097(5) 0.060(4) 0.037(4) 0.024(3) O5 0.0395(19) 0.062(3) 0.031(2) -0.0040(18) 0.0212(16) 0.0099(18) O6 0.0344(19) 0.073(3) 0.040(2) -0.007(2) 0.0224(17) 0.0067(19) O7 0.038(2) 0.050(2) 0.038(2) -0.0027(18) 0.0114(16) -0.0009(17) O8 0.071(3) 0.067(3) 0.069(3) -0.011(3) 0.048(3) 0.003(2) O9 0.0723(18) 0.0697(18) 0.0750(19) 0.000 0.0357(12) 0.000 _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 O6 1.932(4) . ? Zn1 O1 1.958(4) . ? Zn1 O3 1.985(5) 4_545 ? Zn1 O7 2.010(4) . ? Zn1 Na1 3.495(2) . ? Na1 O2 2.311(5) . ? Na1 O8 2.320(5) . ? Na1 O5 2.361(4) . ? Na1 O5 2.410(5) 2 ? Na1 O9 2.416(6) . ? Na1 O3 2.489(6) 4_545 ? Na1 Na1 3.196(4) 2 ? Na1 H9 2.5867 . ? C1 O2 1.213(7) . ? C1 O1 1.280(7) . ? C1 C2 1.525(7) . ? C2 C7 1.387(8) . ? C2 C3 1.396(7) . ? C3 C4 1.396(7) . ? C3 Cl1 1.732(5) . ? C4 C5 1.381(7) . ? C4 Cl2 1.732(5) . ? C5 C6 1.402(7) . ? C5 C8 1.516(8) . ? C6 C7 1.385(7) . ? C6 Cl4 1.734(5) . ? C7 Cl3 1.736(5) . ? C8 O4 1.215(9) . ? C8 O3 1.259(8) . ? C9 O5 1.219(7) . ? C9 O6 1.278(7) . ? C9 C10 1.534(6) . ? C10 C11 1.370(8) . ? C10 C12 1.396(8) . ? C11 C12 1.412(6) 5_576 ? C11 Cl5 1.732(6) . ? C12 C11 1.412(6) 5_576 ? C12 Cl6 1.732(5) . ? C13 O7 1.230(9) . ? C13 N1 1.318(12) . ? C13 H13 0.9300 . ? C14 N1 1.466(13) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N1 1.469(13) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O8 1.237(8) . ? C16 N2 1.331(8) . ? C16 H16 0.9300 . ? C17 N2 1.453(9) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N2 1.450(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C19 1.08(3) 2 ? C19 O9 1.337(18) . ? C19 H19A 0.9608 . ? C19 H19B 0.9608 . ? C19 H19C 0.9609 . ? O3 Zn1 1.985(5) 4 ? O3 Na1 2.489(6) 4 ? O5 Na1 2.410(5) 2 ? O9 C19 1.337(18) 2 ? O9 Na1 2.416(6) 2 ? O9 H9 0.8200 . ? 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 O6 Zn1 O1 116.88(19) . . ? O6 Zn1 O3 107.3(2) . 4_545 ? O1 Zn1 O3 107.95(19) . 4_545 ? O6 Zn1 O7 96.48(17) . . ? O1 Zn1 O7 93.93(18) . . ? O3 Zn1 O7 134.63(19) 4_545 . ? O6 Zn1 Na1 84.43(13) . . ? O1 Zn1 Na1 86.48(13) . . ? O3 Zn1 Na1 44.10(15) 4_545 . ? O7 Zn1 Na1 178.70(13) . . ? O2 Na1 O8 94.09(19) . . ? O2 Na1 O5 98.23(18) . . ? O8 Na1 O5 166.4(2) . . ? O2 Na1 O5 98.84(17) . 2 ? O8 Na1 O5 100.27(18) . 2 ? O5 Na1 O5 83.46(16) . 2 ? O2 Na1 O9 176.2(2) . . ? O8 Na1 O9 88.78(18) . . ? O5 Na1 O9 79.16(16) . . ? O5 Na1 O9 78.20(15) 2 . ? O2 Na1 O3 81.53(17) . 4_545 ? O8 Na1 O3 93.97(18) . 4_545 ? O5 Na1 O3 82.32(15) . 4_545 ? O5 Na1 O3 165.67(16) 2 4_545 ? O9 Na1 O3 100.75(15) . 4_545 ? O2 Na1 Na1 127.62(13) . 2 ? O8 Na1 Na1 125.81(16) . 2 ? O5 Na1 Na1 48.61(11) . 2 ? O5 Na1 Na1 47.28(10) 2 2 ? O9 Na1 Na1 48.59(14) . 2 ? O3 Na1 Na1 121.75(15) 4_545 2 ? O2 Na1 Zn1 60.69(12) . . ? O8 Na1 Zn1 119.45(15) . . ? O5 Na1 Zn1 63.03(11) . . ? O5 Na1 Zn1 135.07(13) 2 . ? O9 Na1 Zn1 119.83(8) . . ? O3 Na1 Zn1 33.72(11) 4_545 . ? Na1 Na1 Zn1 111.47(9) 2 . ? O2 Na1 H9 160.5 . . ? O8 Na1 H9 103.0 . . ? O5 Na1 H9 64.0 . . ? O5 Na1 H9 87.4 2 . ? O9 Na1 H9 18.5 . . ? O3 Na1 H9 87.9 4_545 . ? Na1 Na1 H9 46.9 2 . ? Zn1 Na1 H9 102.1 . . ? O2 C1 O1 128.5(5) . . ? O2 C1 C2 118.5(5) . . ? O1 C1 C2 113.0(5) . . ? C7 C2 C3 118.7(5) . . ? C7 C2 C1 119.6(5) . . ? C3 C2 C1 121.7(5) . . ? C4 C3 C2 120.7(5) . . ? C4 C3 Cl1 120.2(4) . . ? C2 C3 Cl1 119.2(4) . . ? C5 C4 C3 120.4(5) . . ? C5 C4 Cl2 119.4(4) . . ? C3 C4 Cl2 120.1(4) . . ? C4 C5 C6 118.8(5) . . ? C4 C5 C8 121.4(5) . . ? C6 C5 C8 119.5(5) . . ? C7 C6 C5 120.6(5) . . ? C7 C6 Cl4 120.9(4) . . ? C5 C6 Cl4 118.5(4) . . ? C6 C7 C2 120.7(5) . . ? C6 C7 Cl3 120.2(4) . . ? C2 C7 Cl3 119.0(4) . . ? O4 C8 O3 124.2(6) . . ? O4 C8 C5 118.7(6) . . ? O3 C8 C5 117.1(6) . . ? O5 C9 O6 128.1(5) . . ? O5 C9 C10 119.9(5) . . ? O6 C9 C10 112.0(4) . . ? C11 C10 C12 120.3(4) . . ? C11 C10 C9 120.4(5) . . ? C12 C10 C9 119.3(5) . . ? C10 C11 C12 120.2(5) . 5_576 ? C10 C11 Cl5 120.3(4) . . ? C12 C11 Cl5 119.5(4) 5_576 . ? C10 C12 C11 119.5(5) . 5_576 ? C10 C12 Cl6 119.5(4) . . ? C11 C12 Cl6 121.0(4) 5_576 . ? O7 C13 N1 124.2(8) . . ? O7 C13 H13 117.9 . . ? N1 C13 H13 117.9 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O8 C16 N2 125.4(7) . . ? O8 C16 H16 117.3 . . ? N2 C16 H16 117.3 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 C19 O9 66.2(8) 2 . ? C19 C19 H19A 51.2 2 . ? O9 C19 H19A 116.4 . . ? C19 C19 H19B 133.1 2 . ? O9 C19 H19B 105.6 . . ? H19A C19 H19B 108.4 . . ? C19 C19 H19C 118.0 2 . ? O9 C19 H19C 109.4 . . ? H19A C19 H19C 108.4 . . ? H19B C19 H19C 108.4 . . ? C13 N1 C14 122.1(9) . . ? C13 N1 C15 119.2(8) . . ? C14 N1 C15 117.9(9) . . ? C16 N2 C18 120.2(6) . . ? C16 N2 C17 121.7(6) . . ? C18 N2 C17 118.1(6) . . ? C1 O1 Zn1 119.4(4) . . ? C1 O2 Na1 143.7(4) . . ? C8 O3 Zn1 107.2(5) . 4 ? C8 O3 Na1 146.5(4) . 4 ? Zn1 O3 Na1 102.18(17) 4 4 ? C9 O5 Na1 138.8(3) . . ? C9 O5 Na1 136.8(3) . 2 ? Na1 O5 Na1 84.12(15) . 2 ? C9 O6 Zn1 125.1(3) . . ? C13 O7 Zn1 128.4(5) . . ? C16 O8 Na1 123.2(5) . . ? C19 O9 C19 47.6(15) . 2 ? C19 O9 Na1 119.7(8) . . ? C19 O9 Na1 151.3(9) 2 . ? C19 O9 Na1 151.3(9) . 2 ? C19 O9 Na1 119.7(8) 2 2 ? Na1 O9 Na1 82.8(3) . 2 ? C19 O9 H9 116.5 . . ? C19 O9 H9 77.2 2 . ? Na1 O9 H9 92.6 . . ? Na1 O9 H9 76.8 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 O6 Zn1 Na1 O2 115.5(2) . . . . ? O1 Zn1 Na1 O2 -2.00(19) . . . . ? O3 Zn1 Na1 O2 -122.5(2) 4_545 . . . ? O7 Zn1 Na1 O2 -110(6) . . . . ? O6 Zn1 Na1 O8 -167.4(2) . . . . ? O1 Zn1 Na1 O8 75.1(2) . . . . ? O3 Zn1 Na1 O8 -45.4(3) 4_545 . . . ? O7 Zn1 Na1 O8 -33(6) . . . . ? O6 Zn1 Na1 O5 -2.57(19) . . . . ? O1 Zn1 Na1 O5 -120.03(18) . . . . ? O3 Zn1 Na1 O5 119.5(2) 4_545 . . . ? O7 Zn1 Na1 O5 132(6) . . . . ? O6 Zn1 Na1 O5 43.7(2) . . . 2 ? O1 Zn1 Na1 O5 -73.7(2) . . . 2 ? O3 Zn1 Na1 O5 165.8(3) 4_545 . . 2 ? O7 Zn1 Na1 O5 178(100) . . . 2 ? O6 Zn1 Na1 O9 -60.2(2) . . . . ? O1 Zn1 Na1 O9 -177.7(2) . . . . ? O3 Zn1 Na1 O9 61.8(2) 4_545 . . . ? O7 Zn1 Na1 O9 74(6) . . . . ? O6 Zn1 Na1 O3 -122.1(2) . . . 4_545 ? O1 Zn1 Na1 O3 120.5(2) . . . 4_545 ? O7 Zn1 Na1 O3 12(6) . . . 4_545 ? O6 Zn1 Na1 Na1 -6.65(15) . . . 2 ? O1 Zn1 Na1 Na1 -124.10(14) . . . 2 ? O3 Zn1 Na1 Na1 115.4(2) 4_545 . . 2 ? O7 Zn1 Na1 Na1 128(6) . . . 2 ? O2 C1 C2 C7 100.6(7) . . . . ? O1 C1 C2 C7 -78.3(6) . . . . ? O2 C1 C2 C3 -78.2(7) . . . . ? O1 C1 C2 C3 102.9(6) . . . . ? C7 C2 C3 C4 -0.8(7) . . . . ? C1 C2 C3 C4 178.1(5) . . . . ? C7 C2 C3 Cl1 -179.0(4) . . . . ? C1 C2 C3 Cl1 -0.1(7) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? Cl1 C3 C4 C5 178.8(4) . . . . ? C2 C3 C4 Cl2 -176.6(4) . . . . ? Cl1 C3 C4 Cl2 1.6(6) . . . . ? C3 C4 C5 C6 0.4(7) . . . . ? Cl2 C4 C5 C6 177.6(4) . . . . ? C3 C4 C5 C8 -173.8(5) . . . . ? Cl2 C4 C5 C8 3.4(7) . . . . ? C4 C5 C6 C7 -1.1(7) . . . . ? C8 C5 C6 C7 173.2(5) . . . . ? C4 C5 C6 Cl4 177.6(4) . . . . ? C8 C5 C6 Cl4 -8.1(7) . . . . ? C5 C6 C7 C2 0.9(8) . . . . ? Cl4 C6 C7 C2 -177.8(4) . . . . ? C5 C6 C7 Cl3 -177.2(4) . . . . ? Cl4 C6 C7 Cl3 4.1(6) . . . . ? C3 C2 C7 C6 0.0(7) . . . . ? C1 C2 C7 C6 -178.8(5) . . . . ? C3 C2 C7 Cl3 178.2(4) . . . . ? C1 C2 C7 Cl3 -0.7(7) . . . . ? C4 C5 C8 O4 96.3(8) . . . . ? C6 C5 C8 O4 -77.8(8) . . . . ? C4 C5 C8 O3 -84.1(7) . . . . ? C6 C5 C8 O3 101.8(6) . . . . ? O5 C9 C10 C11 -91.4(7) . . . . ? O6 C9 C10 C11 87.8(6) . . . . ? O5 C9 C10 C12 91.1(6) . . . . ? O6 C9 C10 C12 -89.7(7) . . . . ? C12 C10 C11 C12 1.0(9) . . . 5_576 ? C9 C10 C11 C12 -176.5(5) . . . 5_576 ? C12 C10 C11 Cl5 -179.7(4) . . . . ? C9 C10 C11 Cl5 2.8(7) . . . . ? C11 C10 C12 C11 -1.0(9) . . . 5_576 ? C9 C10 C12 C11 176.5(5) . . . 5_576 ? C11 C10 C12 Cl6 178.6(4) . . . . ? C9 C10 C12 Cl6 -3.9(7) . . . . ? O7 C13 N1 C14 178.1(9) . . . . ? O7 C13 N1 C15 8.5(15) . . . . ? O8 C16 N2 C18 2.0(11) . . . . ? O8 C16 N2 C17 -177.0(7) . . . . ? O2 C1 O1 Zn1 -14.5(9) . . . . ? C2 C1 O1 Zn1 164.3(4) . . . . ? O6 Zn1 O1 C1 -74.0(5) . . . . ? O3 Zn1 O1 C1 47.0(5) 4_545 . . . ? O7 Zn1 O1 C1 -173.3(4) . . . . ? Na1 Zn1 O1 C1 7.9(4) . . . . ? O1 C1 O2 Na1 14.4(12) . . . . ? C2 C1 O2 Na1 -164.3(5) . . . . ? O8 Na1 O2 C1 -126.9(7) . . . . ? O5 Na1 O2 C1 47.4(7) . . . . ? O5 Na1 O2 C1 132.0(7) 2 . . . ? O9 Na1 O2 C1 94(2) . . . . ? O3 Na1 O2 C1 -33.5(7) 4_545 . . . ? Na1 Na1 O2 C1 90.3(7) 2 . . . ? Zn1 Na1 O2 C1 -5.3(7) . . . . ? O4 C8 O3 Zn1 10.1(9) . . . 4 ? C5 C8 O3 Zn1 -169.5(4) . . . 4 ? O4 C8 O3 Na1 160.2(6) . . . 4 ? C5 C8 O3 Na1 -19.4(11) . . . 4 ? O6 C9 O5 Na1 6.2(11) . . . . ? C10 C9 O5 Na1 -174.7(4) . . . . ? O6 C9 O5 Na1 177.9(4) . . . 2 ? C10 C9 O5 Na1 -3.0(9) . . . 2 ? O2 Na1 O5 C9 -51.7(6) . . . . ? O8 Na1 O5 C9 103.4(10) . . . . ? O5 Na1 O5 C9 -149.7(6) 2 . . . ? O9 Na1 O5 C9 131.1(6) . . . . ? O3 Na1 O5 C9 28.5(6) 4_545 . . . ? Na1 Na1 O5 C9 174.3(7) 2 . . . ? Zn1 Na1 O5 C9 -0.6(6) . . . . ? O2 Na1 O5 Na1 134.01(16) . . . 2 ? O8 Na1 O5 Na1 -70.9(8) . . . 2 ? O5 Na1 O5 Na1 36.0(2) 2 . . 2 ? O9 Na1 O5 Na1 -43.21(14) . . . 2 ? O3 Na1 O5 Na1 -145.76(16) 4_545 . . 2 ? Zn1 Na1 O5 Na1 -174.94(15) . . . 2 ? O5 C9 O6 Zn1 -10.1(9) . . . . ? C10 C9 O6 Zn1 170.8(4) . . . . ? O1 Zn1 O6 C9 90.0(5) . . . . ? O3 Zn1 O6 C9 -31.4(5) 4_545 . . . ? O7 Zn1 O6 C9 -172.3(5) . . . . ? Na1 Zn1 O6 C9 6.8(5) . . . . ? N1 C13 O7 Zn1 162.7(7) . . . . ? O6 Zn1 O7 C13 142.7(7) . . . . ? O1 Zn1 O7 C13 -99.7(7) . . . . ? O3 Zn1 O7 C13 20.4(8) 4_545 . . . ? Na1 Zn1 O7 C13 9(6) . . . . ? N2 C16 O8 Na1 176.7(5) . . . . ? O2 Na1 O8 C16 -2.2(6) . . . . ? O5 Na1 O8 C16 -157.5(7) . . . . ? O5 Na1 O8 C16 97.6(6) 2 . . . ? O9 Na1 O8 C16 175.4(6) . . . . ? O3 Na1 O8 C16 -83.9(6) 4_545 . . . ? Na1 Na1 O8 C16 141.6(5) 2 . . . ? Zn1 Na1 O8 C16 -60.6(6) . . . . ? C19 C19 O9 Na1 147.8(16) 2 . . . ? C19 C19 O9 Na1 -74(3) 2 . . 2 ? O2 Na1 O9 C19 157(2) . . . . ? O8 Na1 O9 C19 18.0(10) . . . . ? O5 Na1 O9 C19 -155.7(10) . . . . ? O5 Na1 O9 C19 118.8(10) 2 . . . ? O3 Na1 O9 C19 -75.8(10) 4_545 . . . ? Na1 Na1 O9 C19 161.0(10) 2 . . . ? Zn1 Na1 O9 C19 -105.7(10) . . . . ? O2 Na1 O9 C19 -148(3) . . . 2 ? O8 Na1 O9 C19 72.9(16) . . . 2 ? O5 Na1 O9 C19 -100.8(16) . . . 2 ? O5 Na1 O9 C19 173.7(16) 2 . . 2 ? O3 Na1 O9 C19 -20.9(17) 4_545 . . 2 ? Na1 Na1 O9 C19 -144.0(16) 2 . . 2 ? Zn1 Na1 O9 C19 -50.7(17) . . . 2 ? O2 Na1 O9 Na1 -4(2) . . . 2 ? O8 Na1 O9 Na1 -143.04(17) . . . 2 ? O5 Na1 O9 Na1 43.22(10) . . . 2 ? O5 Na1 O9 Na1 -42.29(11) 2 . . 2 ? O3 Na1 O9 Na1 123.14(14) 4_545 . . 2 ? Zn1 Na1 O9 Na1 93.27(11) . . . 2 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.649 _refine_diff_density_min -1.917 _refine_diff_density_rms 0.131 _database_code_depnum_ccdc_archive 'CCDC 943282' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cl6 K N2 O7 Zn' _chemical_formula_weight 675.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.3749(8) _cell_length_b 17.7228(14) _cell_length_c 14.3154(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.919(2) _cell_angle_gamma 90.00 _cell_volume 2518.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6044 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 29.65 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 1.819 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5638 _exptl_absorpt_correction_T_max 0.6099 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 14787 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4933 _reflns_number_gt 3995 _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^)+(0.0974P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4933 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1167 _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 K1 K 0.41279(10) 0.93281(5) 0.41109(6) 0.0473(2) Uani 1 1 d . . . Zn1 Zn 0.51185(4) 1.058251(18) 0.22812(3) 0.02853(14) Uani 1 1 d . . . C1 C 0.3823(4) 0.93103(19) 0.1371(3) 0.0421(9) Uani 1 1 d . . . C2 C 0.3149(4) 0.85465(18) 0.1359(2) 0.0370(8) Uani 1 1 d . . . C3 C 0.1822(4) 0.84189(19) 0.0805(2) 0.0391(8) Uani 1 1 d . . . C4 C 0.1204(4) 0.77249(19) 0.0835(2) 0.0377(7) Uani 1 1 d . . . C5 C 0.1896(3) 0.71553(17) 0.1439(2) 0.0343(7) Uani 1 1 d . . . C6 C 0.3233(4) 0.72755(18) 0.1979(3) 0.0376(7) Uani 1 1 d . . . C7 C 0.3853(3) 0.79668(19) 0.1938(3) 0.0380(7) Uani 1 1 d . . . C8 C 0.3784(4) 1.14127(18) 0.3461(3) 0.0390(8) Uani 1 1 d . . . C9 C 0.7220(3) 1.0178(2) 0.3819(3) 0.0385(8) Uani 1 1 d . . . C10 C 0.8669(3) 1.00796(19) 0.4420(2) 0.0339(7) Uani 1 1 d . . . C11 C 0.9172(4) 0.93712(18) 0.4754(3) 0.0362(7) Uani 1 1 d . . . C12 C 1.0503(4) 0.92987(19) 0.5335(3) 0.0384(7) Uani 1 1 d . . . C13 C 0.0785(6) 0.8421(3) 0.2938(4) 0.0680(13) Uani 1 1 d . . . H13 H 0.0679 0.7899 0.2957 0.082 Uiso 1 1 d R . . C14 C 0.0407(7) 0.9732(3) 0.2577(5) 0.0928(19) Uani 1 1 d . . . H14A H 0.0752 0.9864 0.3255 0.139 Uiso 1 1 calc R . . H14B H -0.0333 1.0057 0.2267 0.139 Uiso 1 1 calc R . . H14C H 0.1106 0.9788 0.2266 0.139 Uiso 1 1 calc R . . C15 C -0.1366(6) 0.8816(4) 0.1899(5) 0.098(2) Uani 1 1 d . . . H15A H -0.1546 0.8284 0.1886 0.148 Uiso 1 1 calc R . . H15B H -0.1456 0.8990 0.1248 0.148 Uiso 1 1 calc R . . H15C H -0.1997 0.9078 0.2157 0.148 Uiso 1 1 calc R . . C16 C 0.6396(7) 1.1645(3) 0.1261(5) 0.096(2) Uani 1 1 d . . . H16A H 0.6366 1.1907 0.0668 0.144 Uiso 1 1 calc R . . H16B H 0.7247 1.1393 0.1503 0.144 Uiso 1 1 calc R . . H16C H 0.6288 1.2000 0.1739 0.144 Uiso 1 1 calc R . . C17 C 0.4013(8) 1.1458(4) 0.0499(4) 0.108(2) Uani 1 1 d . . . H17A H 0.3647 1.1738 0.0936 0.161 Uiso 1 1 calc R . . H17B H 0.3380 1.1078 0.0174 0.161 Uiso 1 1 calc R . . H17C H 0.4185 1.1794 0.0023 0.161 Uiso 1 1 calc R . . Cl1 Cl 0.54970(11) 0.81111(6) 0.26159(10) 0.0677(3) Uani 1 1 d . . . Cl2 Cl 0.41001(12) 0.65704(6) 0.27235(9) 0.0663(3) Uani 1 1 d . . . Cl3 Cl 0.09321(13) 0.91424(6) 0.00966(8) 0.0649(3) Uani 1 1 d . . . Cl4 Cl -0.04254(11) 0.75538(6) 0.01424(8) 0.0598(3) Uani 1 1 d . . . Cl5 Cl 0.81543(10) 0.85913(6) 0.44430(8) 0.0544(3) Uani 1 1 d . . . Cl6 Cl 1.11294(11) 0.84147(5) 0.57420(8) 0.0577(3) Uani 1 1 d . . . N1 N -0.0050(5) 0.8955(2) 0.2493(3) 0.0696(11) Uani 1 1 d . . . N2 N 0.5305(4) 1.10882(15) 0.1066(2) 0.0431(7) Uani 1 1 d . . . H2 H 0.5473 1.0779 0.0664 0.052 Uiso 1 1 d R . . O1 O 0.3925(3) 0.96998(13) 0.21237(17) 0.0396(5) Uani 1 1 d . . . O2 O 0.4255(5) 0.94887(17) 0.0698(2) 0.0815(13) Uani 1 1 d . . . O3 O 0.4380(3) 1.14453(13) 0.27992(18) 0.0420(6) Uani 1 1 d . . . O4 O 0.3675(3) 1.08780(15) 0.3965(2) 0.0597(8) Uani 1 1 d . . . O5 O 0.7014(3) 1.02818(16) 0.29166(18) 0.0465(6) Uani 1 1 d . . . O6 O 0.6348(3) 1.01598(18) 0.4238(2) 0.0542(7) Uani 1 1 d . . . O7 O 0.1936(4) 0.8518(2) 0.3427(3) 0.0800(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0591(5) 0.0419(4) 0.0441(5) -0.0013(3) 0.0200(4) -0.0099(4) Zn1 0.0321(2) 0.0224(2) 0.0314(2) 0.00046(13) 0.00965(16) -0.00047(13) C1 0.058(2) 0.0314(17) 0.042(2) -0.0073(14) 0.0224(18) -0.0190(15) C2 0.049(2) 0.0292(16) 0.0367(18) -0.0094(13) 0.0192(16) -0.0136(14) C3 0.056(2) 0.0297(16) 0.0318(17) -0.0002(13) 0.0126(16) -0.0038(15) C4 0.0431(19) 0.0350(18) 0.0341(17) -0.0050(13) 0.0099(15) -0.0104(14) C5 0.0437(19) 0.0259(15) 0.0356(17) -0.0043(13) 0.0152(15) -0.0096(14) C6 0.0420(19) 0.0283(16) 0.0404(18) -0.0013(14) 0.0086(15) -0.0014(14) C7 0.0358(18) 0.0343(17) 0.0434(19) -0.0076(14) 0.0107(15) -0.0125(14) C8 0.049(2) 0.0273(16) 0.0426(19) 0.0032(14) 0.0162(16) 0.0143(14) C9 0.0336(18) 0.0390(19) 0.0411(19) 0.0020(14) 0.0079(15) 0.0068(14) C10 0.0304(16) 0.0409(18) 0.0303(16) 0.0001(13) 0.0088(13) 0.0044(14) C11 0.0355(18) 0.0352(17) 0.0360(17) -0.0010(13) 0.0073(14) -0.0041(13) C12 0.0421(19) 0.0356(17) 0.0367(18) 0.0035(14) 0.0102(15) 0.0089(14) C13 0.087(4) 0.058(3) 0.071(3) -0.010(2) 0.042(3) -0.019(3) C14 0.119(5) 0.064(3) 0.116(5) -0.006(3) 0.067(4) -0.003(3) C15 0.075(4) 0.122(5) 0.097(5) -0.022(4) 0.023(4) 0.010(4) C16 0.163(7) 0.060(3) 0.096(4) -0.012(3) 0.086(5) -0.038(4) C17 0.136(6) 0.111(5) 0.062(3) 0.026(3) 0.007(4) 0.041(5) Cl1 0.0425(6) 0.0560(6) 0.0909(8) -0.0067(6) -0.0021(5) -0.0137(5) Cl2 0.0686(7) 0.0392(5) 0.0754(8) 0.0115(5) -0.0040(6) 0.0030(5) Cl3 0.0855(8) 0.0395(5) 0.0576(6) 0.0135(5) 0.0017(6) -0.0002(5) Cl4 0.0473(6) 0.0534(6) 0.0657(7) 0.0013(5) -0.0039(5) -0.0113(4) Cl5 0.0496(6) 0.0416(5) 0.0657(6) -0.0035(4) 0.0065(5) -0.0099(4) Cl6 0.0580(6) 0.0363(5) 0.0690(7) 0.0077(4) 0.0032(5) 0.0107(4) N1 0.082(3) 0.063(3) 0.074(3) -0.016(2) 0.040(3) -0.018(2) N2 0.078(2) 0.0280(14) 0.0271(14) 0.0015(11) 0.0208(15) 0.0007(14) O1 0.0544(15) 0.0323(12) 0.0348(12) -0.0094(10) 0.0173(11) -0.0133(11) O2 0.149(4) 0.059(2) 0.0614(19) -0.0251(15) 0.069(2) -0.053(2) O3 0.0561(16) 0.0285(12) 0.0485(14) 0.0008(10) 0.0261(13) 0.0066(11) O4 0.079(2) 0.0364(14) 0.079(2) 0.0199(14) 0.0472(18) 0.0235(14) O5 0.0396(14) 0.0623(16) 0.0340(13) 0.0040(12) 0.0051(11) 0.0099(12) O6 0.0349(14) 0.076(2) 0.0550(16) 0.0077(14) 0.0177(12) 0.0038(13) O7 0.074(2) 0.083(3) 0.080(2) -0.0076(19) 0.018(2) -0.021(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 K1 O7 2.625(4) . ? K1 O6 2.696(3) . ? K1 O6 2.709(3) 3_676 ? K1 O4 2.784(3) . ? K1 O1 2.867(2) . ? K1 O4 3.044(4) 3_676 ? K1 K1 3.5702(17) 3_676 ? K1 Cl1 3.6081(15) . ? K1 Cl4 3.6222(14) 4_676 ? K1 Zn1 3.7981(9) . ? Zn1 O3 1.951(2) . ? Zn1 O1 1.967(2) . ? Zn1 O5 1.984(3) . ? Zn1 N2 2.015(3) . ? C1 O2 1.217(4) . ? C1 O1 1.258(4) . ? C1 C2 1.521(4) . ? C2 C7 1.387(5) . ? C2 C3 1.393(5) . ? C3 C4 1.393(5) . ? C3 Cl3 1.726(4) . ? C4 C5 1.386(5) . ? C4 Cl4 1.720(4) . ? C5 C6 1.394(5) . ? C5 C8 1.519(4) 2_545 ? C6 C7 1.393(5) . ? C6 Cl2 1.717(4) . ? C7 Cl1 1.718(3) . ? C8 O4 1.216(4) . ? C8 O3 1.275(4) . ? C8 C5 1.519(4) 2 ? C9 O6 1.222(4) . ? C9 O5 1.260(4) . ? C9 C10 1.510(5) . ? C10 C12 1.378(5) 3_776 ? C10 C11 1.390(5) . ? C11 C12 1.396(5) . ? C11 Cl5 1.717(3) . ? C12 C10 1.378(5) 3_776 ? C12 Cl6 1.731(3) . ? C13 O7 1.208(6) . ? C13 N1 1.316(7) . ? C13 H13 0.9336 . ? C14 N1 1.450(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N1 1.404(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N2 1.466(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N2 1.501(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? Cl4 K1 3.6222(14) 4_575 ? N2 H2 0.8494 . ? O4 K1 3.044(4) 3_676 ? O6 K1 2.709(3) 3_676 ? 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 O7 K1 O6 162.62(10) . . ? O7 K1 O6 98.65(10) . 3_676 ? O6 K1 O6 97.31(7) . 3_676 ? O7 K1 O4 113.73(12) . . ? O6 K1 O4 65.67(9) . . ? O6 K1 O4 70.44(9) 3_676 . ? O7 K1 O1 87.15(10) . . ? O6 K1 O1 75.87(8) . . ? O6 K1 O1 144.05(9) 3_676 . ? O4 K1 O1 74.74(8) . . ? O7 K1 O4 127.66(10) . 3_676 ? O6 K1 O4 66.70(8) . 3_676 ? O6 K1 O4 61.91(8) 3_676 3_676 ? O4 K1 O4 104.59(7) . 3_676 ? O1 K1 O4 138.15(8) . 3_676 ? O7 K1 K1 146.59(9) . 3_676 ? O6 K1 K1 48.81(6) . 3_676 ? O6 K1 K1 48.51(6) 3_676 3_676 ? O4 K1 K1 55.59(8) . 3_676 ? O1 K1 K1 115.45(6) . 3_676 ? O4 K1 K1 49.00(6) 3_676 3_676 ? O7 K1 Cl1 84.25(9) . . ? O6 K1 Cl1 83.72(7) . . ? O6 K1 Cl1 157.11(7) 3_676 . ? O4 K1 Cl1 129.21(6) . . ? O1 K1 Cl1 58.46(6) . . ? O4 K1 Cl1 98.32(6) 3_676 . ? K1 K1 Cl1 128.05(4) 3_676 . ? O7 K1 Cl4 69.06(9) . 4_676 ? O6 K1 Cl4 118.07(7) . 4_676 ? O6 K1 Cl4 89.25(7) 3_676 4_676 ? O4 K1 Cl4 159.68(7) . 4_676 ? O1 K1 Cl4 125.43(6) . 4_676 ? O4 K1 Cl4 63.08(6) 3_676 4_676 ? K1 K1 Cl4 110.21(4) 3_676 4_676 ? Cl1 K1 Cl4 70.47(3) . 4_676 ? O7 K1 Zn1 116.22(9) . . ? O6 K1 Zn1 47.86(6) . . ? O6 K1 Zn1 124.09(7) 3_676 . ? O4 K1 Zn1 56.25(5) . . ? O1 K1 Zn1 30.44(5) . . ? O4 K1 Zn1 114.37(6) 3_676 . ? K1 K1 Zn1 85.33(3) 3_676 . ? Cl1 K1 Zn1 73.06(3) . . ? Cl4 K1 Zn1 142.36(3) 4_676 . ? O3 Zn1 O1 111.30(10) . . ? O3 Zn1 O5 118.86(11) . . ? O1 Zn1 O5 110.23(12) . . ? O3 Zn1 N2 97.27(11) . . ? O1 Zn1 N2 118.04(11) . . ? O5 Zn1 N2 100.59(13) . . ? O3 Zn1 K1 88.95(7) . . ? O1 Zn1 K1 47.61(7) . . ? O5 Zn1 K1 87.56(8) . . ? N2 Zn1 K1 165.62(9) . . ? O2 C1 O1 125.3(3) . . ? O2 C1 C2 119.7(3) . . ? O1 C1 C2 115.0(3) . . ? C7 C2 C3 118.8(3) . . ? C7 C2 C1 119.4(3) . . ? C3 C2 C1 121.7(3) . . ? C4 C3 C2 120.9(3) . . ? C4 C3 Cl3 120.1(3) . . ? C2 C3 Cl3 119.0(3) . . ? C5 C4 C3 120.2(3) . . ? C5 C4 Cl4 118.3(2) . . ? C3 C4 Cl4 121.4(3) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 C8 121.3(3) . 2_545 ? C6 C5 C8 119.6(3) . 2_545 ? C7 C6 C5 120.6(3) . . ? C7 C6 Cl2 120.1(3) . . ? C5 C6 Cl2 119.4(3) . . ? C2 C7 C6 120.5(3) . . ? C2 C7 Cl1 119.4(2) . . ? C6 C7 Cl1 120.1(3) . . ? O4 C8 O3 128.7(3) . . ? O4 C8 C5 119.6(3) . 2 ? O3 C8 C5 111.7(3) . 2 ? O6 C9 O5 125.3(3) . . ? O6 C9 C10 118.3(3) . . ? O5 C9 C10 116.4(3) . . ? C12 C10 C11 119.4(3) 3_776 . ? C12 C10 C9 119.8(3) 3_776 . ? C11 C10 C9 120.8(3) . . ? C10 C11 C12 119.7(3) . . ? C10 C11 Cl5 119.8(3) . . ? C12 C11 Cl5 120.5(3) . . ? C10 C12 C11 120.9(3) 3_776 . ? C10 C12 Cl6 119.5(3) 3_776 . ? C11 C12 Cl6 119.6(3) . . ? O7 C13 N1 125.4(5) . . ? O7 C13 H13 103.3 . . ? N1 C13 H13 131.4 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 Cl1 K1 85.78(12) . . ? C4 Cl4 K1 112.65(12) . 4_575 ? C13 N1 C15 123.6(5) . . ? C13 N1 C14 119.3(5) . . ? C15 N1 C14 117.0(6) . . ? C16 N2 C17 109.1(5) . . ? C16 N2 Zn1 113.5(3) . . ? C17 N2 Zn1 111.5(3) . . ? C16 N2 H2 105.3 . . ? C17 N2 H2 104.0 . . ? Zn1 N2 H2 112.9 . . ? C1 O1 Zn1 115.3(2) . . ? C1 O1 K1 133.4(2) . . ? Zn1 O1 K1 101.94(9) . . ? C8 O3 Zn1 125.2(2) . . ? C8 O4 K1 140.4(2) . . ? C8 O4 K1 117.1(3) . 3_676 ? K1 O4 K1 75.41(7) . 3_676 ? C9 O5 Zn1 111.1(2) . . ? C9 O6 K1 136.1(3) . . ? C9 O6 K1 140.2(3) . 3_676 ? K1 O6 K1 82.69(7) . 3_676 ? C13 O7 K1 153.7(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 O7 K1 Zn1 O3 101.91(13) . . . . ? O6 K1 Zn1 O3 -86.59(12) . . . . ? O6 K1 Zn1 O3 -20.48(11) 3_676 . . . ? O4 K1 Zn1 O3 -0.24(12) . . . . ? O1 K1 Zn1 O3 120.57(13) . . . . ? O4 K1 Zn1 O3 -91.96(10) 3_676 . . . ? K1 K1 Zn1 O3 -51.39(9) 3_676 . . . ? Cl1 K1 Zn1 O3 176.44(9) . . . . ? Cl4 K1 Zn1 O3 -168.87(10) 4_676 . . . ? O7 K1 Zn1 O1 -18.66(14) . . . . ? O6 K1 Zn1 O1 152.84(13) . . . . ? O6 K1 Zn1 O1 -141.05(13) 3_676 . . . ? O4 K1 Zn1 O1 -120.81(14) . . . . ? O4 K1 Zn1 O1 147.47(12) 3_676 . . . ? K1 K1 Zn1 O1 -171.96(11) 3_676 . . . ? Cl1 K1 Zn1 O1 55.87(10) . . . . ? Cl4 K1 Zn1 O1 70.56(11) 4_676 . . . ? O7 K1 Zn1 O5 -139.14(13) . . . . ? O6 K1 Zn1 O5 32.36(12) . . . . ? O6 K1 Zn1 O5 98.47(11) 3_676 . . . ? O4 K1 Zn1 O5 118.71(12) . . . . ? O1 K1 Zn1 O5 -120.48(13) . . . . ? O4 K1 Zn1 O5 26.99(10) 3_676 . . . ? K1 K1 Zn1 O5 67.56(9) 3_676 . . . ? Cl1 K1 Zn1 O5 -64.62(8) . . . . ? Cl4 K1 Zn1 O5 -49.93(9) 4_676 . . . ? O7 K1 Zn1 N2 -14.1(4) . . . . ? O6 K1 Zn1 N2 157.4(4) . . . . ? O6 K1 Zn1 N2 -136.4(4) 3_676 . . . ? O4 K1 Zn1 N2 -116.2(4) . . . . ? O1 K1 Zn1 N2 4.6(4) . . . . ? O4 K1 Zn1 N2 152.1(4) 3_676 . . . ? K1 K1 Zn1 N2 -167.4(4) 3_676 . . . ? Cl1 K1 Zn1 N2 60.5(4) . . . . ? Cl4 K1 Zn1 N2 75.2(4) 4_676 . . . ? O2 C1 C2 C7 103.1(5) . . . . ? O1 C1 C2 C7 -74.4(4) . . . . ? O2 C1 C2 C3 -79.2(5) . . . . ? O1 C1 C2 C3 103.3(4) . . . . ? C7 C2 C3 C4 0.4(5) . . . . ? C1 C2 C3 C4 -177.3(3) . . . . ? C7 C2 C3 Cl3 179.0(3) . . . . ? C1 C2 C3 Cl3 1.3(4) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? Cl3 C3 C4 C5 -176.9(3) . . . . ? C2 C3 C4 Cl4 -179.0(2) . . . . ? Cl3 C3 C4 Cl4 2.4(4) . . . . ? C3 C4 C5 C6 -2.8(5) . . . . ? Cl4 C4 C5 C6 177.8(2) . . . . ? C3 C4 C5 C8 175.7(3) . . . 2_545 ? Cl4 C4 C5 C8 -3.6(4) . . . 2_545 ? C4 C5 C6 C7 2.0(5) . . . . ? C8 C5 C6 C7 -176.6(3) 2_545 . . . ? C4 C5 C6 Cl2 -179.6(3) . . . . ? C8 C5 C6 Cl2 1.8(4) 2_545 . . . ? C3 C2 C7 C6 -1.2(5) . . . . ? C1 C2 C7 C6 176.5(3) . . . . ? C3 C2 C7 Cl1 179.3(2) . . . . ? C1 C2 C7 Cl1 -2.9(4) . . . . ? C5 C6 C7 C2 0.0(5) . . . . ? Cl2 C6 C7 C2 -178.3(3) . . . . ? C5 C6 C7 Cl1 179.5(2) . . . . ? Cl2 C6 C7 Cl1 1.1(4) . . . . ? O6 C9 C10 C12 -101.8(4) . . . 3_776 ? O5 C9 C10 C12 77.4(4) . . . 3_776 ? O6 C9 C10 C11 76.4(4) . . . . ? O5 C9 C10 C11 -104.4(4) . . . . ? C12 C10 C11 C12 0.2(5) 3_776 . . . ? C9 C10 C11 C12 -177.9(3) . . . . ? C12 C10 C11 Cl5 -179.3(3) 3_776 . . . ? C9 C10 C11 Cl5 2.5(4) . . . . ? C10 C11 C12 C10 -0.2(5) . . . 3_776 ? Cl5 C11 C12 C10 179.3(3) . . . 3_776 ? C10 C11 C12 Cl6 -179.5(3) . . . . ? Cl5 C11 C12 Cl6 0.1(4) . . . . ? C2 C7 Cl1 K1 71.1(3) . . . . ? C6 C7 Cl1 K1 -108.3(3) . . . . ? O7 K1 Cl1 C7 23.66(15) . . . . ? O6 K1 Cl1 C7 -143.77(14) . . . . ? O6 K1 Cl1 C7 122.3(2) 3_676 . . . ? O4 K1 Cl1 C7 -92.43(16) . . . . ? O1 K1 Cl1 C7 -66.52(13) . . . . ? O4 K1 Cl1 C7 150.96(13) 3_676 . . . ? K1 K1 Cl1 C7 -165.72(13) 3_676 . . . ? Cl4 K1 Cl1 C7 93.46(12) 4_676 . . . ? Zn1 K1 Cl1 C7 -96.00(12) . . . . ? C5 C4 Cl4 K1 -40.5(3) . . . 4_575 ? C3 C4 Cl4 K1 140.2(3) . . . 4_575 ? O7 C13 N1 C15 177.5(5) . . . . ? O7 C13 N1 C14 0.0(7) . . . . ? O3 Zn1 N2 C16 71.8(3) . . . . ? O1 Zn1 N2 C16 -169.3(3) . . . . ? O5 Zn1 N2 C16 -49.4(3) . . . . ? K1 Zn1 N2 C16 -173.1(4) . . . . ? O3 Zn1 N2 C17 -51.8(4) . . . . ? O1 Zn1 N2 C17 67.0(4) . . . . ? O5 Zn1 N2 C17 -173.1(4) . . . . ? K1 Zn1 N2 C17 63.2(5) . . . . ? O2 C1 O1 Zn1 -9.7(6) . . . . ? C2 C1 O1 Zn1 167.6(3) . . . . ? O2 C1 O1 K1 -149.5(4) . . . . ? C2 C1 O1 K1 27.9(5) . . . . ? O3 Zn1 O1 C1 141.2(3) . . . . ? O5 Zn1 O1 C1 -84.7(3) . . . . ? N2 Zn1 O1 C1 30.0(3) . . . . ? K1 Zn1 O1 C1 -151.3(3) . . . . ? O3 Zn1 O1 K1 -67.52(12) . . . . ? O5 Zn1 O1 K1 66.57(11) . . . . ? N2 Zn1 O1 K1 -178.71(11) . . . . ? O7 K1 O1 C1 -53.4(3) . . . . ? O6 K1 O1 C1 122.9(3) . . . . ? O6 K1 O1 C1 -154.2(3) 3_676 . . . ? O4 K1 O1 C1 -168.9(3) . . . . ? O4 K1 O1 C1 96.1(3) 3_676 . . . ? K1 K1 O1 C1 152.2(3) 3_676 . . . ? Cl1 K1 O1 C1 31.6(3) . . . . ? Cl4 K1 O1 C1 8.3(4) 4_676 . . . ? Zn1 K1 O1 C1 143.3(4) . . . . ? O7 K1 O1 Zn1 163.30(13) . . . . ? O6 K1 O1 Zn1 -20.43(10) . . . . ? O6 K1 O1 Zn1 62.48(18) 3_676 . . . ? O4 K1 O1 Zn1 47.75(11) . . . . ? O4 K1 O1 Zn1 -47.23(16) 3_676 . . . ? K1 K1 O1 Zn1 8.88(12) 3_676 . . . ? Cl1 K1 O1 Zn1 -111.70(11) . . . . ? Cl4 K1 O1 Zn1 -135.03(7) 4_676 . . . ? O4 C8 O3 Zn1 8.4(6) . . . . ? C5 C8 O3 Zn1 -169.3(2) 2 . . . ? O1 Zn1 O3 C8 39.7(3) . . . . ? O5 Zn1 O3 C8 -90.0(3) . . . . ? N2 Zn1 O3 C8 163.7(3) . . . . ? K1 Zn1 O3 C8 -3.3(3) . . . . ? O3 C8 O4 K1 -10.5(8) . . . . ? C5 C8 O4 K1 167.0(3) 2 . . . ? O3 C8 O4 K1 89.6(5) . . . 3_676 ? C5 C8 O4 K1 -92.9(4) 2 . . 3_676 ? O7 K1 O4 C8 -101.3(5) . . . . ? O6 K1 O4 C8 59.6(4) . . . . ? O6 K1 O4 C8 167.6(5) 3_676 . . . ? O1 K1 O4 C8 -21.5(4) . . . . ? O4 K1 O4 C8 115.1(5) 3_676 . . . ? K1 K1 O4 C8 115.1(5) 3_676 . . . ? Cl1 K1 O4 C8 1.2(5) . . . . ? Cl4 K1 O4 C8 165.0(3) 4_676 . . . ? Zn1 K1 O4 C8 5.3(4) . . . . ? O7 K1 O4 K1 143.53(10) . . . 3_676 ? O6 K1 O4 K1 -55.50(8) . . . 3_676 ? O6 K1 O4 K1 52.49(7) 3_676 . . 3_676 ? O1 K1 O4 K1 -136.62(8) . . . 3_676 ? O4 K1 O4 K1 0.0 3_676 . . 3_676 ? Cl1 K1 O4 K1 -113.91(8) . . . 3_676 ? Cl4 K1 O4 K1 49.9(2) 4_676 . . 3_676 ? Zn1 K1 O4 K1 -109.81(8) . . . 3_676 ? O6 C9 O5 Zn1 9.4(5) . . . . ? C10 C9 O5 Zn1 -169.7(2) . . . . ? O3 Zn1 O5 C9 54.0(3) . . . . ? O1 Zn1 O5 C9 -76.2(3) . . . . ? N2 Zn1 O5 C9 158.5(2) . . . . ? K1 Zn1 O5 C9 -33.4(2) . . . . ? O5 C9 O6 K1 58.9(5) . . . . ? C10 C9 O6 K1 -122.0(3) . . . . ? O5 C9 O6 K1 -137.0(3) . . . 3_676 ? C10 C9 O6 K1 42.1(5) . . . 3_676 ? O7 K1 O6 C9 -33.6(6) . . . . ? O6 K1 O6 C9 169.8(4) 3_676 . . . ? O4 K1 O6 C9 -125.5(4) . . . . ? O1 K1 O6 C9 -46.1(3) . . . . ? O4 K1 O6 C9 114.7(4) 3_676 . . . ? K1 K1 O6 C9 169.8(4) 3_676 . . . ? Cl1 K1 O6 C9 12.9(3) . . . . ? Cl4 K1 O6 C9 76.8(4) 4_676 . . . ? Zn1 K1 O6 C9 -59.9(3) . . . . ? O7 K1 O6 K1 156.6(4) . . . 3_676 ? O6 K1 O6 K1 0.0 3_676 . . 3_676 ? O4 K1 O6 K1 64.63(9) . . . 3_676 ? O1 K1 O6 K1 144.03(9) . . . 3_676 ? O4 K1 O6 K1 -55.10(7) 3_676 . . 3_676 ? Cl1 K1 O6 K1 -156.97(7) . . . 3_676 ? Cl4 K1 O6 K1 -93.07(7) 4_676 . . 3_676 ? Zn1 K1 O6 K1 130.23(10) . . . 3_676 ? N1 C13 O7 K1 -10.4(11) . . . . ? O6 K1 O7 C13 -64.1(9) . . . . ? O6 K1 O7 C13 92.4(7) 3_676 . . . ? O4 K1 O7 C13 20.0(8) . . . . ? O1 K1 O7 C13 -51.9(7) . . . . ? O4 K1 O7 C13 153.4(7) 3_676 . . . ? K1 K1 O7 C13 83.0(8) 3_676 . . . ? Cl1 K1 O7 C13 -110.5(7) . . . . ? Cl4 K1 O7 C13 178.3(8) 4_676 . . . ? Zn1 K1 O7 C13 -42.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.715 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.169 _database_code_depnum_ccdc_archive 'CCDC 943283' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H54 Cd8 F32 O59' _chemical_formula_weight 3274.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.426(3) _cell_length_b 47.197(8) _cell_length_c 7.0539(13) _cell_angle_alpha 90.00 _cell_angle_beta 107.580(8) _cell_angle_gamma 90.00 _cell_volume 4578.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3719 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 23.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3164 _exptl_absorpt_coefficient_mu 2.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6044 _exptl_absorpt_correction_T_max 0.6674 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 Smart Apex CCD' _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 13993 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_k_max 58 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 0.86 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4513 _reflns_number_gt 3061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0517P)^2^+28.6747P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4513 _refine_ls_number_parameters 374 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 2.371 _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 C1 C 0.2422(6) 0.77771(14) 0.2585(14) 0.030(3) Uani 1 1 d G . . C2 C 0.3261(5) 0.76381(17) 0.3689(13) 0.035(3) Uani 1 1 d GD . . C3 C 0.3300(5) 0.73438(17) 0.3691(13) 0.033(3) Uani 1 1 d GD . . C4 C 0.2499(6) 0.71885(14) 0.2588(13) 0.026(3) Uani 1 1 d G . . C5 C 0.1660(5) 0.73276(18) 0.1485(12) 0.033(3) Uani 1 1 d GD . . C6 C 0.1622(5) 0.76218(18) 0.1483(13) 0.038(4) Uani 1 1 d GD . . C7 C 0.2454(11) 0.8079(3) 0.237(2) 0.032(3) Uani 1 1 d . . . C8 C 0.2545(11) 0.6873(3) 0.269(2) 0.035(4) Uani 1 1 d . . . C9 C 0.5000 0.9392(4) 0.2500 0.028(4) Uani 1 2 d S . . C10 C 0.5000 0.9701(4) 0.2500 0.025(4) Uani 1 2 d S . . C11 C 0.5818(9) 0.9866(2) 0.2393(17) 0.017(2) Uani 1 1 d . . . C12 C 0.5832(9) 1.0147(2) 0.2414(17) 0.017(2) Uani 1 1 d . . . C13 C 0.5000 1.0301(4) 0.2500 0.032(5) Uani 1 2 d S . . C14 C 0.5000 1.0608(4) 0.2500 0.032(5) Uani 1 2 d S . . C15 C 0.0000 0.9441(4) 0.2500 0.028(4) Uani 1 2 d S . . C16 C 0.0000 0.9742(4) 0.2500 0.027(4) Uani 1 2 d S . . C17 C 0.0841(9) 0.9900(2) 0.3465(17) 0.018(2) Uani 1 1 d . . . C18 C 0.0826(10) 1.0196(3) 0.3477(18) 0.024(3) Uani 1 1 d . . . C19 C 0.0000 1.0351(4) 0.2500 0.036(5) Uani 1 2 d S . . C20 C 0.0000 1.0644(4) 0.2500 0.041(6) Uani 1 2 d S . . Cd1 Cd 0.24837(7) 0.86707(2) 0.23480(14) 0.0278(3) Uani 1 1 d . . . Cd2 Cd 0.5000 0.88113(3) 0.2500 0.0294(4) Uani 1 2 d S . . Cd3 Cd 0.0000 0.88495(3) 0.2500 0.0304(4) Uani 1 2 d S . . F1 F 0.4005(6) 0.77860(18) 0.4764(14) 0.042(2) Uani 1 1 d D . . F2 F 0.4045(7) 0.72177(19) 0.4723(13) 0.042(2) Uani 1 1 d D . . F3 F 0.0920(7) 0.71844(19) 0.0424(12) 0.042(2) Uani 1 1 d D . . F4 F 0.0852(7) 0.77524(19) 0.0452(14) 0.043(2) Uani 1 1 d D . . F5 F 0.6580(5) 0.97322(15) 0.2224(11) 0.0263(17) Uani 1 1 d . . . F6 F 0.6589(5) 1.02914(15) 0.2188(11) 0.0221(15) Uani 1 1 d . . . F7 F 0.1629(5) 0.97633(15) 0.4492(11) 0.0263(17) Uani 1 1 d . . . F8 F 0.1639(6) 1.03083(15) 0.4486(11) 0.0275(17) Uani 1 1 d . . . O1 O 0.3240(8) 0.8228(2) 0.3182(15) 0.034(2) Uani 1 1 d . . . O2 O 0.1707(7) 0.82433(19) 0.1654(14) 0.030(2) Uani 1 1 d . . . O3 O 0.1820(8) 0.6717(2) 0.2310(14) 0.035(2) Uani 1 1 d . . . O4 O 0.3308(8) 0.6732(2) 0.3055(15) 0.037(2) Uani 1 1 d . . . O5 O 0.4220(7) 0.92627(18) 0.1562(13) 0.027(2) Uani 1 1 d . . . O6 O 0.5741(7) 1.07381(18) 0.3505(12) 0.025(2) Uani 1 1 d . . . O7 O -0.0724(7) 0.93017(19) 0.2676(13) 0.025(2) Uani 1 1 d . . . O8 O 0.0758(7) 1.0780(2) 0.2629(14) 0.030(2) Uani 1 1 d . . . O1W O 0.5000 0.8350(3) 0.2500 0.030(3) Uani 1 2 d S . . H1X H 0.5361 0.8282 0.1649 0.036 Uiso 0.50 1 d PR . . H1Y H 0.4343 0.8282 0.2022 0.036 Uiso 0.50 1 d PR . . O2W O 0.2519(7) 0.91306(19) 0.2350(14) 0.029(2) Uani 1 1 d . . . H2X H 0.1986 0.9194 0.1582 0.035 Uiso 1 1 d R . . H2Y H 0.2987 0.9188 0.1950 0.035 Uiso 1 1 d R . . O3W O 0.0000 0.8364(3) 0.2500 0.034(3) Uani 1 2 d S . . H3X H -0.0618 0.8296 0.1677 0.040 Uiso 0.50 1 d PR . . H3Y H 0.0505 0.8296 0.1989 0.040 Uiso 0.50 1 d PR . . O4W O 0.4085(8) 0.8770(2) 0.4641(14) 0.036(2) Uani 1 1 d . . . H4X H 0.4286 0.8634 0.5455 0.043 Uiso 1 1 d R . . H4Y H 0.4087 0.8922 0.5285 0.043 Uiso 1 1 d R . . O5W O 0.3400(7) 0.8725(2) 0.0115(14) 0.033(2) Uani 1 1 d . . . H5X H 0.3204 0.8865 -0.0667 0.039 Uiso 1 1 d R . . H5Y H 0.3395 0.8576 -0.0557 0.039 Uiso 1 1 d R . . O6W O 0.1589(7) 0.8744(2) 0.4619(14) 0.029(2) Uani 1 1 d . . . H6X H 0.1818 0.8882 0.5394 0.035 Uiso 1 1 d R . . H6Y H 0.1590 0.8596 0.5308 0.035 Uiso 1 1 d R . . O7W O 0.0884(14) 0.8758(4) 0.015(3) 0.031(5) Uani 0.50 1 d P . . H7X H 0.0660 0.8616 -0.0589 0.037 Uiso 0.50 1 d PR . . H7Y H 0.0877 0.8903 -0.0581 0.037 Uiso 0.50 1 d PR . . O8W O 0.2511(15) 0.9238(5) 0.734(3) 0.035(5) Uani 0.50 1 d P . . H8X H 0.2549 0.9380 0.6618 0.042 Uiso 0.50 1 d PR . . H8Y H 0.2157 0.9280 0.8062 0.042 Uiso 0.50 1 d PR . . O9W O 0.0000 0.8419(3) 0.7500 0.029(3) Uani 1 2 d S . . H9X H 0.0328 0.8393 0.6696 0.035 Uiso 0.50 1 d PR . . H9Y H -0.0075 0.8261 0.8022 0.035 Uiso 0.50 1 d PR . . O10W O 0.5000 0.8310(6) 0.7500 0.032(7) Uani 0.50 2 d SP . . H10X H 0.4638 0.8271 0.8217 0.039 Uiso 0.25 1 d PR . . H10Y H 0.5064 0.8163 0.6848 0.039 Uiso 0.25 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.017(7) 0.033(7) 0.036(8) 0.000(6) 0.001(6) 0.002(6) C2 0.033(9) 0.045(9) 0.034(8) -0.001(7) 0.019(7) 0.010(7) C3 0.024(8) 0.037(8) 0.038(8) -0.010(6) 0.009(6) -0.003(6) C4 0.037(8) 0.018(7) 0.025(7) -0.004(5) 0.013(6) -0.006(6) C5 0.025(8) 0.045(8) 0.029(7) 0.010(6) 0.008(6) -0.001(7) C6 0.033(9) 0.051(9) 0.035(8) 0.029(7) 0.016(7) -0.004(7) C7 0.034(9) 0.032(8) 0.029(7) -0.003(6) 0.009(6) -0.011(6) C8 0.028(8) 0.025(7) 0.054(10) -0.013(6) 0.015(7) 0.000(6) C9 0.021(10) 0.021(9) 0.041(11) 0.000 0.009(9) 0.000 C10 0.029(10) 0.018(9) 0.036(10) 0.000 0.021(9) 0.000 C11 0.022(7) 0.016(5) 0.017(6) 0.001(4) 0.011(5) 0.006(5) C12 0.021(7) 0.018(6) 0.013(5) -0.005(4) 0.009(5) -0.008(5) C13 0.023(11) 0.022(10) 0.048(12) 0.000 0.006(9) 0.000 C14 0.045(14) 0.016(9) 0.038(11) 0.000 0.018(10) 0.000 C15 0.028(11) 0.027(10) 0.025(10) 0.000 0.000(8) 0.000 C16 0.030(11) 0.024(9) 0.026(10) 0.000 0.005(8) 0.000 C17 0.018(7) 0.014(6) 0.020(6) -0.006(4) 0.004(5) -0.002(5) C18 0.025(8) 0.028(7) 0.018(6) 0.005(5) 0.006(5) 0.002(6) C19 0.042(13) 0.034(11) 0.029(11) 0.000 0.006(9) 0.000 C20 0.075(18) 0.017(9) 0.033(11) 0.000 0.020(12) 0.000 Cd1 0.0304(6) 0.0250(6) 0.0279(6) -0.0002(4) 0.0089(4) 0.0000(4) Cd2 0.0290(9) 0.0257(8) 0.0339(8) 0.000 0.0101(6) 0.000 Cd3 0.0285(9) 0.0269(8) 0.0368(9) 0.000 0.0115(7) 0.000 F1 0.034(5) 0.041(5) 0.052(5) -0.003(4) 0.016(4) -0.007(4) F2 0.044(6) 0.052(5) 0.031(5) -0.005(4) 0.011(4) 0.008(5) F3 0.042(5) 0.056(6) 0.027(4) 0.018(4) 0.007(4) -0.004(5) F4 0.034(5) 0.052(6) 0.045(5) 0.003(4) 0.014(4) 0.013(4) F5 0.022(4) 0.026(4) 0.032(4) -0.004(3) 0.009(3) 0.008(3) F6 0.014(4) 0.026(4) 0.031(4) 0.002(3) 0.012(3) 0.000(3) F7 0.021(4) 0.024(4) 0.028(4) 0.010(3) -0.002(3) 0.006(3) F8 0.026(4) 0.021(4) 0.026(4) -0.009(3) -0.007(3) -0.005(3) O1 0.040(6) 0.029(5) 0.034(5) 0.007(4) 0.013(5) -0.005(5) O2 0.029(6) 0.025(5) 0.037(5) -0.018(4) 0.009(4) 0.002(4) O3 0.039(6) 0.034(5) 0.034(5) -0.014(4) 0.016(5) -0.016(5) O4 0.036(6) 0.033(5) 0.040(6) 0.010(4) 0.009(5) 0.006(5) O5 0.033(6) 0.019(4) 0.026(5) -0.003(4) 0.005(4) -0.006(4) O6 0.027(5) 0.029(5) 0.020(4) 0.008(4) 0.011(4) -0.006(4) O7 0.027(5) 0.030(5) 0.027(5) -0.007(4) 0.021(4) -0.006(4) O8 0.025(5) 0.032(5) 0.034(5) 0.006(4) 0.010(4) -0.007(4) O1W 0.033(8) 0.023(7) 0.037(8) 0.000 0.014(6) 0.000 O2W 0.031(6) 0.017(4) 0.039(6) 0.002(4) 0.009(5) 0.004(4) O3W 0.041(9) 0.010(6) 0.053(9) 0.000 0.018(7) 0.000 O4W 0.042(6) 0.035(5) 0.029(5) 0.008(4) 0.009(5) 0.004(5) O5W 0.038(6) 0.033(5) 0.028(5) -0.008(4) 0.011(4) 0.004(4) O6W 0.028(5) 0.030(5) 0.031(5) -0.008(4) 0.011(4) -0.012(4) O7W 0.028(11) 0.021(9) 0.034(10) -0.012(8) -0.006(8) -0.013(8) O8W 0.038(13) 0.044(13) 0.027(10) -0.003(8) 0.016(9) -0.017(10) O9W 0.021(7) 0.031(7) 0.034(7) 0.000 0.006(6) 0.000 O10W 0.013(13) 0.06(2) 0.020(13) 0.000 0.002(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.437(16) . ? C2 F1 1.313(10) . ? C2 C3 1.3900 . ? C3 F2 1.253(11) . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C4 C8 1.492(16) . ? C5 F3 1.294(10) . ? C5 C6 1.3900 . ? C6 F4 1.286(10) . ? C7 O2 1.299(18) . ? C7 O1 1.309(17) . ? C8 O3 1.240(17) . ? C8 O4 1.244(17) . ? C9 O5 1.275(13) 2_655 ? C9 O5 1.275(13) . ? C9 C10 1.46(2) . ? C9 Cd2 2.740(18) . ? C10 C11 1.435(15) . ? C10 C11 1.435(15) 2_655 ? C11 F5 1.302(14) . ? C11 C12 1.328(16) . ? C12 F6 1.337(14) . ? C12 C13 1.421(15) . ? C13 C12 1.421(15) 2_655 ? C13 C14 1.45(3) . ? C14 O6 1.250(13) . ? C14 O6 1.250(13) 2_655 ? C15 O7 1.271(13) 2 ? C15 O7 1.271(13) . ? C15 C16 1.42(3) . ? C16 C17 1.410(15) . ? C16 C17 1.410(15) 2 ? C17 F7 1.316(14) . ? C17 C18 1.399(17) . ? C18 F8 1.288(15) . ? C18 C19 1.391(17) . ? C19 C20 1.38(3) . ? C19 C18 1.391(17) 2 ? C20 O8 1.246(13) . ? C20 O8 1.246(13) 2 ? Cd1 O2W 2.171(9) . ? Cd1 O2 2.288(9) . ? Cd1 O1 2.347(10) . ? Cd1 O5W 2.356(10) . ? Cd1 O6W 2.366(10) . ? Cd1 O7W 2.397(19) . ? Cd1 O4W 2.431(11) . ? Cd2 O1W 2.177(13) . ? Cd2 O4W 2.295(11) 2_655 ? Cd2 O4W 2.295(11) . ? Cd2 O5 2.407(9) . ? Cd2 O5 2.407(9) 2_655 ? Cd2 O5W 2.445(10) . ? Cd2 O5W 2.445(10) 2_655 ? Cd3 O3W 2.292(12) . ? Cd3 O6W 2.381(10) . ? Cd3 O6W 2.381(10) 2 ? Cd3 O7 2.396(9) . ? Cd3 O7 2.396(9) 2 ? Cd3 O7W 2.42(2) 2 ? Cd3 O7W 2.42(2) . ? O1W H1X 0.9600 . ? O1W H1Y 0.9600 . ? O2W H2X 0.8500 . ? O2W H2Y 0.8498 . ? O3W H3X 0.9600 . ? O3W H3Y 0.9600 . ? O4W H4X 0.8500 . ? O4W H4Y 0.8498 . ? O5W H5X 0.8500 . ? O5W H5Y 0.8501 . ? O6W H6X 0.8502 . ? O6W H6Y 0.8500 . ? O7W H7X 0.8497 . ? O7W H7Y 0.8503 . ? O8W H8X 0.8501 . ? O8W H8Y 0.8501 . ? O9W H9X 0.8500 . ? O9W H9Y 0.8501 . ? O10W H10X 0.8500 . ? O10W H10Y 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.0 . . ? C2 C1 C7 118.5(8) . . ? C6 C1 C7 120.8(8) . . ? F1 C2 C1 119.6(7) . . ? F1 C2 C3 120.4(7) . . ? C1 C2 C3 120.0 . . ? F2 C3 C4 119.8(7) . . ? F2 C3 C2 120.2(7) . . ? C4 C3 C2 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 C8 118.8(8) . . ? C5 C4 C8 121.1(8) . . ? F3 C5 C6 119.7(7) . . ? F3 C5 C4 120.3(7) . . ? C6 C5 C4 120.0 . . ? F4 C6 C5 120.4(7) . . ? F4 C6 C1 119.5(7) . . ? C5 C6 C1 120.0 . . ? O2 C7 O1 111.0(12) . . ? O2 C7 C1 125.7(12) . . ? O1 C7 C1 122.5(12) . . ? O3 C8 O4 111.3(13) . . ? O3 C8 C4 124.1(13) . . ? O4 C8 C4 124.5(13) . . ? O5 C9 O5 122.9(17) 2_655 . ? O5 C9 C10 118.5(8) 2_655 . ? O5 C9 C10 118.5(8) . . ? O5 C9 Cd2 61.5(8) 2_655 . ? O5 C9 Cd2 61.5(8) . . ? C10 C9 Cd2 180.000(2) . . ? C11 C10 C11 114.3(15) . 2_655 ? C11 C10 C9 122.8(7) . . ? C11 C10 C9 122.8(7) 2_655 . ? F5 C11 C12 118.2(12) . . ? F5 C11 C10 118.2(10) . . ? C12 C11 C10 123.5(12) . . ? C11 C12 F6 121.3(11) . . ? C11 C12 C13 120.1(12) . . ? F6 C12 C13 118.4(11) . . ? C12 C13 C12 118.5(16) 2_655 . ? C12 C13 C14 120.8(8) 2_655 . ? C12 C13 C14 120.8(8) . . ? O6 C14 O6 121.4(17) . 2_655 ? O6 C14 C13 119.3(9) . . ? O6 C14 C13 119.3(9) 2_655 . ? O7 C15 O7 117.8(17) 2 . ? O7 C15 C16 121.1(8) 2 . ? O7 C15 C16 121.1(8) . . ? C17 C16 C17 116.5(16) . 2 ? C17 C16 C15 121.8(8) . . ? C17 C16 C15 121.8(8) 2 . ? F7 C17 C18 119.9(11) . . ? F7 C17 C16 118.8(11) . . ? C18 C17 C16 121.1(12) . . ? F8 C18 C19 123.9(12) . . ? F8 C18 C17 113.6(11) . . ? C19 C18 C17 122.5(13) . . ? C20 C19 C18 121.8(9) . 2 ? C20 C19 C18 121.8(9) . . ? C18 C19 C18 116.4(18) 2 . ? O8 C20 O8 118.2(18) . 2 ? O8 C20 C19 120.9(9) . . ? O8 C20 C19 120.9(9) 2 . ? O2W Cd1 O2 153.1(4) . . ? O2W Cd1 O1 151.7(4) . . ? O2 Cd1 O1 55.2(4) . . ? O2W Cd1 O5W 82.7(4) . . ? O2 Cd1 O5W 106.9(3) . . ? O1 Cd1 O5W 87.3(4) . . ? O2W Cd1 O6W 82.6(4) . . ? O2 Cd1 O6W 86.6(3) . . ? O1 Cd1 O6W 105.5(3) . . ? O5W Cd1 O6W 165.3(3) . . ? O2W Cd1 O7W 81.1(5) . . ? O2 Cd1 O7W 72.5(5) . . ? O1 Cd1 O7W 126.9(5) . . ? O5W Cd1 O7W 99.9(6) . . ? O6W Cd1 O7W 78.4(6) . . ? O2W Cd1 O4W 77.9(4) . . ? O2 Cd1 O4W 128.1(3) . . ? O1 Cd1 O4W 74.2(3) . . ? O5W Cd1 O4W 79.2(3) . . ? O6W Cd1 O4W 97.1(3) . . ? O7W Cd1 O4W 158.9(5) . . ? O1W Cd2 O4W 85.1(3) . 2_655 ? O1W Cd2 O4W 85.1(3) . . ? O4W Cd2 O4W 170.2(5) 2_655 . ? O1W Cd2 O5 152.3(2) . . ? O4W Cd2 O5 102.1(3) 2_655 . ? O4W Cd2 O5 86.7(3) . . ? O1W Cd2 O5 152.3(2) . 2_655 ? O4W Cd2 O5 86.7(3) 2_655 2_655 ? O4W Cd2 O5 102.1(3) . 2_655 ? O5 Cd2 O5 55.5(4) . 2_655 ? O1W Cd2 O5W 80.5(2) . . ? O4W Cd2 O5W 98.3(3) 2_655 . ? O4W Cd2 O5W 80.0(3) . . ? O5 Cd2 O5W 72.0(3) . . ? O5 Cd2 O5W 127.0(3) 2_655 . ? O1W Cd2 O5W 80.5(2) . 2_655 ? O4W Cd2 O5W 80.0(3) 2_655 2_655 ? O4W Cd2 O5W 98.3(3) . 2_655 ? O5 Cd2 O5W 127.0(3) . 2_655 ? O5 Cd2 O5W 72.0(3) 2_655 2_655 ? O5W Cd2 O5W 160.9(5) . 2_655 ? O1W Cd2 C9 180.000(3) . . ? O4W Cd2 C9 94.9(3) 2_655 . ? O4W Cd2 C9 94.9(3) . . ? O5 Cd2 C9 27.7(2) . . ? O5 Cd2 C9 27.7(2) 2_655 . ? O5W Cd2 C9 99.5(2) . . ? O5W Cd2 C9 99.5(2) 2_655 . ? O3W Cd3 O6W 77.9(2) . . ? O3W Cd3 O6W 77.9(2) . 2 ? O6W Cd3 O6W 155.8(4) . 2 ? O3W Cd3 O7 153.0(2) . . ? O6W Cd3 O7 120.4(3) . . ? O6W Cd3 O7 82.4(3) 2 . ? O3W Cd3 O7 153.0(2) . 2 ? O6W Cd3 O7 82.4(3) . 2 ? O6W Cd3 O7 120.4(3) 2 2 ? O7 Cd3 O7 54.0(4) . 2 ? O3W Cd3 O7W 79.8(4) . 2 ? O6W Cd3 O7W 98.0(5) . 2 ? O6W Cd3 O7W 77.7(5) 2 2 ? O7 Cd3 O7W 78.1(5) . 2 ? O7 Cd3 O7W 121.5(5) 2 2 ? O3W Cd3 O7W 79.8(4) . . ? O6W Cd3 O7W 77.7(5) . . ? O6W Cd3 O7W 98.0(5) 2 . ? O7 Cd3 O7W 121.5(5) . . ? O7 Cd3 O7W 78.1(5) 2 . ? O7W Cd3 O7W 159.5(9) 2 . ? C7 O1 Cd1 95.3(9) . . ? C7 O2 Cd1 98.4(8) . . ? C9 O5 Cd2 90.8(9) . . ? C15 O7 Cd3 94.1(9) . . ? Cd2 O1W H1X 109.5 . . ? Cd2 O1W H1Y 109.5 . . ? H1X O1W H1Y 109.5 . . ? Cd1 O2W H2X 109.5 . . ? Cd1 O2W H2Y 109.7 . . ? H2X O2W H2Y 109.5 . . ? Cd3 O3W H3X 109.5 . . ? Cd3 O3W H3Y 109.5 . . ? H3X O3W H3Y 109.5 . . ? Cd2 O4W Cd1 101.4(4) . . ? Cd2 O4W H4X 111.2 . . ? Cd1 O4W H4X 111.5 . . ? Cd2 O4W H4Y 111.7 . . ? Cd1 O4W H4Y 111.6 . . ? H4X O4W H4Y 109.3 . . ? Cd1 O5W Cd2 99.3(3) . . ? Cd1 O5W H5X 112.0 . . ? Cd2 O5W H5X 112.2 . . ? Cd1 O5W H5Y 111.8 . . ? Cd2 O5W H5Y 111.6 . . ? H5X O5W H5Y 109.6 . . ? Cd1 O6W Cd3 103.0(4) . . ? Cd1 O6W H6X 111.2 . . ? Cd3 O6W H6X 110.9 . . ? Cd1 O6W H6Y 111.2 . . ? Cd3 O6W H6Y 111.4 . . ? H6X O6W H6Y 109.1 . . ? Cd1 O7W Cd3 100.9(7) . . ? Cd1 O7W H7X 111.9 . . ? Cd3 O7W H7X 112.1 . . ? Cd1 O7W H7Y 111.3 . . ? Cd3 O7W H7Y 111.0 . . ? H7X O7W H7Y 109.4 . . ? H8X O8W H8Y 109.5 . . ? H9X O9W H9Y 109.5 . . ? H10X O10W H10Y 109.5 . . ? 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 C6 C1 C2 F1 -178.4(10) . . . . ? C7 C1 C2 F1 11.0(11) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C7 C1 C2 C3 -170.7(10) . . . . ? F1 C2 C3 F2 0.1(11) . . . . ? C1 C2 C3 F2 -178.2(10) . . . . ? F1 C2 C3 C4 178.3(10) . . . . ? C1 C2 C3 C4 0.0 . . . . ? F2 C3 C4 C5 178.2(10) . . . . ? C2 C3 C4 C5 0.0 . . . . ? F2 C3 C4 C8 1.0(11) . . . . ? C2 C3 C4 C8 -177.3(11) . . . . ? C3 C4 C5 F3 178.6(9) . . . . ? C8 C4 C5 F3 -4.2(11) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C8 C4 C5 C6 177.2(11) . . . . ? F3 C5 C6 F4 0.7(10) . . . . ? C4 C5 C6 F4 179.4(10) . . . . ? F3 C5 C6 C1 -178.6(9) . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 C1 C6 F4 -179.4(9) . . . . ? C7 C1 C6 F4 -8.9(11) . . . . ? C2 C1 C6 C5 0.0 . . . . ? C7 C1 C6 C5 170.5(11) . . . . ? C2 C1 C7 O2 -168.9(11) . . . . ? C6 C1 C7 O2 20.5(18) . . . . ? C2 C1 C7 O1 -0.4(17) . . . . ? C6 C1 C7 O1 -171.0(10) . . . . ? C3 C4 C8 O3 156.9(12) . . . . ? C5 C4 C8 O3 -20.3(19) . . . . ? C3 C4 C8 O4 -27.4(19) . . . . ? C5 C4 C8 O4 155.4(12) . . . . ? O5 C9 C10 C11 37.7(7) 2_655 . . . ? O5 C9 C10 C11 -142.3(7) . . . . ? Cd2 C9 C10 C11 3(100) . . . . ? O5 C9 C10 C11 -142.3(7) 2_655 . . 2_655 ? O5 C9 C10 C11 37.7(7) . . . 2_655 ? Cd2 C9 C10 C11 -177(100) . . . 2_655 ? C11 C10 C11 F5 -177.8(12) 2_655 . . . ? C9 C10 C11 F5 2.2(12) . . . . ? C11 C10 C11 C12 0.8(9) 2_655 . . . ? C9 C10 C11 C12 -179.2(9) . . . . ? F5 C11 C12 F6 2.7(18) . . . . ? C10 C11 C12 F6 -175.8(9) . . . . ? F5 C11 C12 C13 177.0(9) . . . . ? C10 C11 C12 C13 -1.5(17) . . . . ? C11 C12 C13 C12 0.8(8) . . . 2_655 ? F6 C12 C13 C12 175.2(11) . . . 2_655 ? C11 C12 C13 C14 -179.2(8) . . . . ? F6 C12 C13 C14 -4.8(11) . . . . ? C12 C13 C14 O6 139.0(7) 2_655 . . . ? C12 C13 C14 O6 -41.0(7) . . . . ? C12 C13 C14 O6 -41.0(7) 2_655 . . 2_655 ? C12 C13 C14 O6 139.0(7) . . . 2_655 ? O7 C15 C16 C17 -39.0(7) 2 . . . ? O7 C15 C16 C17 141.0(7) . . . . ? O7 C15 C16 C17 141.0(7) 2 . . 2 ? O7 C15 C16 C17 -39.0(7) . . . 2 ? C17 C16 C17 F7 175.8(12) 2 . . . ? C15 C16 C17 F7 -4.2(12) . . . . ? C17 C16 C17 C18 1.0(9) 2 . . . ? C15 C16 C17 C18 -179.0(9) . . . . ? F7 C17 C18 F8 2.6(18) . . . . ? C16 C17 C18 F8 177.4(9) . . . . ? F7 C17 C18 C19 -176.8(9) . . . . ? C16 C17 C18 C19 -2.0(18) . . . . ? F8 C18 C19 C20 1.7(14) . . . . ? C17 C18 C19 C20 -179.0(9) . . . . ? F8 C18 C19 C18 -178.3(14) . . . 2 ? C17 C18 C19 C18 1.0(9) . . . 2 ? C18 C19 C20 O8 -150.9(8) 2 . . . ? C18 C19 C20 O8 29.1(8) . . . . ? C18 C19 C20 O8 29.1(8) 2 . . 2 ? C18 C19 C20 O8 -150.9(8) . . . 2 ? O5 C9 Cd2 O1W 146(100) 2_655 . . . ? O5 C9 Cd2 O1W -34(100) . . . . ? C10 C9 Cd2 O1W 0(22) . . . . ? O5 C9 Cd2 O4W -73.3(5) 2_655 . . 2_655 ? O5 C9 Cd2 O4W 106.7(5) . . . 2_655 ? C10 C9 Cd2 O4W -39(100) . . . 2_655 ? O5 C9 Cd2 O4W 106.7(5) 2_655 . . . ? O5 C9 Cd2 O4W -73.3(5) . . . . ? C10 C9 Cd2 O4W 141(100) . . . . ? O5 C9 Cd2 O5 180.000(6) 2_655 . . . ? C10 C9 Cd2 O5 -146(100) . . . . ? O5 C9 Cd2 O5 180.000(6) . . . 2_655 ? C10 C9 Cd2 O5 34(100) . . . 2_655 ? O5 C9 Cd2 O5W -172.6(5) 2_655 . . . ? O5 C9 Cd2 O5W 7.4(5) . . . . ? C10 C9 Cd2 O5W -138(100) . . . . ? O5 C9 Cd2 O5W 7.4(5) 2_655 . . 2_655 ? O5 C9 Cd2 O5W -172.6(5) . . . 2_655 ? C10 C9 Cd2 O5W 42(100) . . . 2_655 ? O2 C7 O1 Cd1 -2.7(12) . . . . ? C1 C7 O1 Cd1 -172.8(11) . . . . ? O2W Cd1 O1 C7 179.8(8) . . . . ? O2 Cd1 O1 C7 1.8(8) . . . . ? O5W Cd1 O1 C7 -111.0(8) . . . . ? O6W Cd1 O1 C7 76.3(8) . . . . ? O7W Cd1 O1 C7 -10.7(11) . . . . ? O4W Cd1 O1 C7 169.5(9) . . . . ? O1 C7 O2 Cd1 2.8(12) . . . . ? C1 C7 O2 Cd1 172.5(12) . . . . ? O2W Cd1 O2 C7 -179.7(8) . . . . ? O1 Cd1 O2 C7 -1.8(8) . . . . ? O5W Cd1 O2 C7 72.5(9) . . . . ? O6W Cd1 O2 C7 -113.3(8) . . . . ? O7W Cd1 O2 C7 167.8(10) . . . . ? O4W Cd1 O2 C7 -16.9(10) . . . . ? O5 C9 O5 Cd2 0.000(4) 2_655 . . . ? C10 C9 O5 Cd2 180.000(3) . . . . ? O1W Cd2 O5 C9 180.000(6) . . . . ? O4W Cd2 O5 C9 -77.3(5) 2_655 . . . ? O4W Cd2 O5 C9 107.1(5) . . . . ? O5 Cd2 O5 C9 0.000(2) 2_655 . . . ? O5W Cd2 O5 C9 -172.3(5) . . . . ? O5W Cd2 O5 C9 9.2(6) 2_655 . . . ? O7 C15 O7 Cd3 0.0 2 . . . ? C16 C15 O7 Cd3 180.0 . . . . ? O3W Cd3 O7 C15 180.000(2) . . . . ? O6W Cd3 O7 C15 51.9(6) . . . . ? O6W Cd3 O7 C15 -136.8(5) 2 . . . ? O7 Cd3 O7 C15 0.0 2 . . . ? O7W Cd3 O7 C15 144.3(7) 2 . . . ? O7W Cd3 O7 C15 -42.0(7) . . . . ? O1W Cd2 O4W Cd1 -79.6(3) . . . . ? O4W Cd2 O4W Cd1 -79.6(3) 2_655 . . . ? O5 Cd2 O4W Cd1 73.8(4) . . . . ? O5 Cd2 O4W Cd1 127.5(3) 2_655 . . . ? O5W Cd2 O4W Cd1 1.5(3) . . . . ? O5W Cd2 O4W Cd1 -159.2(4) 2_655 . . . ? C9 Cd2 O4W Cd1 100.4(3) . . . . ? O2W Cd1 O4W Cd2 -86.3(4) . . . . ? O2 Cd1 O4W Cd2 101.5(4) . . . . ? O1 Cd1 O4W Cd2 88.7(4) . . . . ? O5W Cd1 O4W Cd2 -1.6(3) . . . . ? O6W Cd1 O4W Cd2 -167.2(4) . . . . ? O7W Cd1 O4W Cd2 -91.0(15) . . . . ? O2W Cd1 O5W Cd2 80.4(4) . . . . ? O2 Cd1 O5W Cd2 -125.3(3) . . . . ? O1 Cd1 O5W Cd2 -73.0(4) . . . . ? O6W Cd1 O5W Cd2 78.1(13) . . . . ? O7W Cd1 O5W Cd2 160.0(5) . . . . ? O4W Cd1 O5W Cd2 1.5(3) . . . . ? O1W Cd2 O5W Cd1 85.1(3) . . . . ? O4W Cd2 O5W Cd1 168.7(4) 2_655 . . . ? O4W Cd2 O5W Cd1 -1.5(3) . . . . ? O5 Cd2 O5W Cd1 -91.2(4) . . . . ? O5 Cd2 O5W Cd1 -99.2(4) 2_655 . . . ? O5W Cd2 O5W Cd1 85.1(3) 2_655 . . . ? C9 Cd2 O5W Cd1 -94.9(3) . . . . ? O2W Cd1 O6W Cd3 80.3(4) . . . . ? O2 Cd1 O6W Cd3 -74.9(4) . . . . ? O1 Cd1 O6W Cd3 -127.4(4) . . . . ? O5W Cd1 O6W Cd3 82.7(13) . . . . ? O7W Cd1 O6W Cd3 -2.1(5) . . . . ? O4W Cd1 O6W Cd3 157.0(4) . . . . ? O3W Cd3 O6W Cd1 84.1(3) . . . . ? O6W Cd3 O6W Cd1 84.1(3) 2 . . . ? O7 Cd3 O6W Cd1 -117.4(3) . . . . ? O7 Cd3 O6W Cd1 -77.4(3) 2 . . . ? O7W Cd3 O6W Cd1 161.7(6) 2 . . . ? O7W Cd3 O6W Cd1 2.1(5) . . . . ? O2W Cd1 O7W Cd3 -82.2(6) . . . . ? O2 Cd1 O7W Cd3 92.1(6) . . . . ? O1 Cd1 O7W Cd3 102.8(6) . . . . ? O5W Cd1 O7W Cd3 -163.1(5) . . . . ? O6W Cd1 O7W Cd3 2.0(5) . . . . ? O4W Cd1 O7W Cd3 -77.6(17) . . . . ? O3W Cd3 O7W Cd1 -81.7(5) . . . . ? O6W Cd3 O7W Cd1 -2.0(5) . . . . ? O6W Cd3 O7W Cd1 -157.8(5) 2 . . . ? O7 Cd3 O7W Cd1 116.3(6) . . . . ? O7 Cd3 O7W Cd1 82.7(6) 2 . . . ? O7W Cd3 O7W Cd1 -81.7(5) 2 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.905 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.129 _database_code_depnum_ccdc_archive 'CCDC 943284' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H20 Cl4 O14 Zn' _chemical_formula_weight 547.41 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' Zn Zn 0.2839 1.4301 '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 5.349(2) _cell_length_b 12.309(6) _cell_length_c 15.159(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.851(9) _cell_angle_gamma 90.00 _cell_volume 992.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2756 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 29.81 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6463 _exptl_absorpt_correction_T_max 0.7099 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5257 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1741 _reflns_number_gt 1541 _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^)+(0.0619P)^2^+9.9896P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1741 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1716 _refine_ls_wR_factor_gt 0.1689 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.0000 1.0000 0.0000 0.0238(3) Uani 1 2 d S . . C1 C 0.1713(11) 0.0621(5) 0.5520(4) 0.0214(13) Uani 1 1 d . . . C2 C 0.1648(11) 0.0643(5) 0.4597(4) 0.0203(12) Uani 1 1 d . . . C3 C -0.0065(11) 0.0024(5) 0.4066(4) 0.0215(13) Uani 1 1 d . . . C4 C -0.0175(12) 0.0066(5) 0.3056(4) 0.0254(14) Uani 1 1 d . . . Cl1 Cl 0.3960(3) 0.13736(15) 0.61513(11) 0.0355(5) Uani 1 1 d . . . Cl2 Cl 0.3830(3) 0.14202(14) 0.41035(11) 0.0326(4) Uani 1 1 d . . . O1 O -0.0724(10) 0.0944(4) 0.2682(3) 0.0346(12) Uani 1 1 d . . . O2 O 0.0287(10) -0.0801(4) 0.2664(3) 0.0318(11) Uani 1 1 d . . . O3 O 0.2113(9) 0.9296(4) 0.1079(3) 0.0369(12) Uani 1 1 d . . . H3A H 0.3553 0.9013 0.1050 0.055 Uiso 1 1 d R . . H3B H 0.1927 0.9445 0.1616 0.055 Uiso 1 1 d R . . O4 O 0.2210(9) 0.9322(4) -0.0892(3) 0.0366(12) Uani 1 1 d . . . H4A H 0.1665 0.9027 -0.1381 0.055 Uiso 1 1 d R . . H4B H 0.3781 0.9210 -0.0791 0.055 Uiso 1 1 d R . . O5 O 0.2621(9) 1.1293(4) 0.0138(3) 0.0333(11) Uani 1 1 d . . . H5A H 0.3040 1.1684 -0.0286 0.050 Uiso 1 1 d R . . H5B H 0.3296 1.1546 0.0627 0.050 Uiso 1 1 d R . . O6 O 0.1476(9) 0.7041(4) 0.6514(3) 0.0349(11) Uani 1 1 d . . . H6A H 0.2554 0.6657 0.6825 0.052 Uiso 1 1 d R . . H6B H 0.1487 0.7683 0.6722 0.052 Uiso 1 1 d R . . O7 O 0.3427(10) 0.2082(4) 0.1783(3) 0.0425(13) Uani 1 1 d . . . H7A H 0.2649 0.1815 0.2193 0.064 Uiso 1 1 d R . . H7B H 0.3671 0.2756 0.1876 0.064 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0257(6) 0.0263(6) 0.0191(5) -0.0007(4) 0.0016(4) 0.0003(4) C1 0.022(3) 0.022(3) 0.020(3) -0.004(2) 0.001(2) -0.001(2) C2 0.019(3) 0.023(3) 0.020(3) 0.002(2) 0.003(2) -0.002(2) C3 0.023(3) 0.023(3) 0.017(3) -0.001(2) -0.002(2) 0.002(2) C4 0.030(3) 0.028(3) 0.018(3) 0.001(3) 0.002(2) 0.001(3) Cl1 0.0340(9) 0.0437(10) 0.0276(8) -0.0089(7) -0.0033(7) -0.0149(8) Cl2 0.0323(9) 0.0355(9) 0.0306(9) 0.0054(7) 0.0064(7) -0.0101(7) O1 0.053(3) 0.030(3) 0.020(2) 0.0019(19) 0.001(2) 0.009(2) O2 0.047(3) 0.028(2) 0.020(2) -0.0016(19) 0.005(2) 0.004(2) O3 0.040(3) 0.050(3) 0.022(2) 0.007(2) 0.009(2) 0.018(2) O4 0.028(2) 0.056(3) 0.024(2) -0.009(2) -0.0030(19) 0.014(2) O5 0.037(3) 0.034(3) 0.028(2) -0.003(2) 0.003(2) -0.008(2) O6 0.043(3) 0.030(3) 0.031(3) -0.003(2) -0.001(2) 0.004(2) O7 0.052(3) 0.037(3) 0.037(3) -0.002(2) -0.004(2) -0.006(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 Zn1 O4 2.061(5) . ? Zn1 O4 2.061(5) 3_575 ? Zn1 O3 2.080(5) 3_575 ? Zn1 O3 2.080(5) . ? Zn1 O5 2.117(5) 3_575 ? Zn1 O5 2.117(5) . ? C1 C3 1.383(9) 3_556 ? C1 C2 1.396(8) . ? C1 Cl1 1.727(6) . ? C2 C3 1.385(9) . ? C2 Cl2 1.737(6) . ? C3 C1 1.383(9) 3_556 ? C3 C4 1.527(8) . ? C4 O1 1.242(8) . ? C4 O2 1.257(8) . ? O3 H3A 0.8502 . ? O3 H3B 0.8502 . ? O4 H4A 0.8501 . ? O4 H4B 0.8501 . ? O5 H5A 0.8506 . ? O5 H5A 0.8506 . ? O5 H5B 0.8506 . ? O6 H6A 0.8500 . ? O6 H6B 0.8500 . ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O4 180.000(1) . 3_575 ? O4 Zn1 O3 87.42(19) . 3_575 ? O4 Zn1 O3 92.58(19) 3_575 3_575 ? O4 Zn1 O3 92.58(19) . . ? O4 Zn1 O3 87.42(19) 3_575 . ? O3 Zn1 O3 180.0(3) 3_575 . ? O4 Zn1 O5 92.8(2) . 3_575 ? O4 Zn1 O5 87.2(2) 3_575 3_575 ? O3 Zn1 O5 86.2(2) 3_575 3_575 ? O3 Zn1 O5 93.8(2) . 3_575 ? O4 Zn1 O5 87.2(2) . . ? O4 Zn1 O5 92.8(2) 3_575 . ? O3 Zn1 O5 93.8(2) 3_575 . ? O3 Zn1 O5 86.2(2) . . ? O5 Zn1 O5 180.000(1) 3_575 . ? C3 C1 C2 120.9(6) 3_556 . ? C3 C1 Cl1 119.7(5) 3_556 . ? C2 C1 Cl1 119.3(5) . . ? C3 C2 C1 121.3(6) . . ? C3 C2 Cl2 119.1(5) . . ? C1 C2 Cl2 119.6(5) . . ? C1 C3 C2 117.8(5) 3_556 . ? C1 C3 C4 120.9(5) 3_556 . ? C2 C3 C4 121.3(6) . . ? O1 C4 O2 124.9(6) . . ? O1 C4 C3 118.0(6) . . ? O2 C4 C3 117.1(5) . . ? Zn1 O3 H3A 123.5 . . ? Zn1 O3 H3B 123.7 . . ? H3A O3 H3B 109.5 . . ? Zn1 O4 H4A 125.2 . . ? Zn1 O4 H4B 124.7 . . ? H4A O4 H4B 109.4 . . ? H5A O5 Zn1 125.0 . . ? H5A O5 H5A 0.0 . . ? Zn1 O5 H5A 125.0 . . ? H5A O5 H5B 109.3 . . ? Zn1 O5 H5B 125.4 . . ? H5A O5 H5B 109.3 . . ? H6A O6 H6B 109.5 . . ? H7A O7 H7B 109.5 . . ? 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 C3 C1 C2 C3 0.1(10) 3_556 . . . ? Cl1 C1 C2 C3 177.8(5) . . . . ? C3 C1 C2 Cl2 -177.4(5) 3_556 . . . ? Cl1 C1 C2 Cl2 0.3(7) . . . . ? C1 C2 C3 C1 -0.1(10) . . . 3_556 ? Cl2 C2 C3 C1 177.4(5) . . . 3_556 ? C1 C2 C3 C4 178.7(6) . . . . ? Cl2 C2 C3 C4 -3.8(8) . . . . ? C1 C3 C4 O1 116.1(7) 3_556 . . . ? C2 C3 C4 O1 -62.7(9) . . . . ? C1 C3 C4 O2 -63.5(8) 3_556 . . . ? C2 C3 C4 O2 117.7(7) . . . . ? O4 Zn1 O5 H5A 56.6 . . . . ? O4 Zn1 O5 H5A -123.4 3_575 . . . ? O3 Zn1 O5 H5A -30.7 3_575 . . . ? O3 Zn1 O5 H5A 149.3 . . . . ? O5 Zn1 O5 H5A -172.0 3_575 . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.609 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.207 _database_code_depnum_ccdc_archive 'CCDC 943285'