# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Wickleder, Mathias' _publ_contact_author_email mathias.wickleder@uni-oldenburg.de _publ_section_title ; Para-Benzene Disulfonic Acid and its Tetrachloro and Tetrafluoro Derivates - Studies Towards Polyhalogenated Metal-Organic-Frameworks with Sulfo Analogues of Terephthalic Acid ; _publ_author_name M.Wickleder data_e:\cz02\cz02 _database_code_depnum_ccdc_archive 'CCDC 763637' #TrackingRef '335_web_deposit_cif_file_0_ChristinaZitzer_1264609785.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N2 O8 S2 Zn' _chemical_formula_weight 447.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7662(4) _cell_length_b 9.8685(4) _cell_length_c 10.1440(4) _cell_angle_alpha 69.106(2) _cell_angle_beta 68.746(2) _cell_angle_gamma 86.295(2) _cell_volume 848.89(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30921 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 35.00 _reflns_number_total 7458 _reflns_number_gt 4895 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0314P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7458 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.5000 0.01085(4) Uani 1 2 d S . . S1 S 0.70958(3) 0.65245(3) 0.10878(3) 0.01139(5) Uani 1 1 d . . . O11 O 0.63067(9) 0.56336(9) 0.26638(8) 0.01726(16) Uani 1 1 d . . . O12 O 0.62700(8) 0.65894(8) 0.01113(8) 0.01383(14) Uani 1 1 d . . . O13 O 0.76063(9) 0.79624(8) 0.08628(9) 0.02016(17) Uani 1 1 d . . . C11 C 0.86987(11) 0.56222(11) 0.04796(11) 0.01184(18) Uani 1 1 d . . . C12 C 0.91917(12) 0.46254(12) 0.15546(12) 0.0145(2) Uani 1 1 d . . . H1 H 0.8691(16) 0.4438(14) 0.2501(16) 0.018(3) Uiso 1 1 d . . . C13 C 0.94882(12) 0.59995(12) -0.10655(12) 0.0145(2) Uani 1 1 d . . . H2 H 0.9116(15) 0.6645(14) -0.1789(15) 0.017(3) Uiso 1 1 d . . . C1 C 0.35397(13) 0.74754(12) 0.34613(13) 0.0181(2) Uani 1 1 d . . . H11 H 0.4181(15) 0.7452(14) 0.2506(15) 0.022(4) Uiso 1 1 d . . . O1 O 0.35397(9) 0.65421(8) 0.46702(9) 0.01627(15) Uani 1 1 d . . . N1 N 0.26470(12) 0.85406(10) 0.33999(11) 0.0206(2) Uani 1 1 d . . . C2 C 0.2657(2) 0.96016(18) 0.19592(19) 0.0399(4) Uani 1 1 d . . . H21 H 0.340(2) 0.9451(19) 0.116(2) 0.048(5) Uiso 1 1 d . . . H22 H 0.284(2) 1.054(2) 0.190(2) 0.065(6) Uiso 1 1 d . . . H23 H 0.170(2) 0.950(2) 0.191(2) 0.062(6) Uiso 1 1 d . . . C3 C 0.15626(17) 0.86709(15) 0.47704(17) 0.0280(3) Uani 1 1 d . . . H31 H 0.1555(17) 0.9641(18) 0.4698(17) 0.035(4) Uiso 1 1 d . . . H32 H 0.1811(18) 0.8053(19) 0.563(2) 0.050(5) Uiso 1 1 d . . . H33 H 0.0646(18) 0.8382(17) 0.4857(18) 0.037(5) Uiso 1 1 d . . . Zn2 Zn 0.5000 0.5000 0.0000 0.01079(4) Uani 1 2 d S . . S2 S 0.70629(3) 0.64460(3) 0.61730(3) 0.01116(5) Uani 1 1 d . . . O21 O 0.62555(8) 0.65499(8) 0.51763(8) 0.01417(14) Uani 1 1 d . . . O22 O 0.62913(9) 0.54633(8) 0.77222(8) 0.01588(15) Uani 1 1 d . . . O23 O 0.75132(9) 0.78654(8) 0.60601(9) 0.01882(16) Uani 1 1 d . . . C21 C 0.87005(11) 0.56090(11) 0.55147(11) 0.01158(18) Uani 1 1 d . . . C22 C 0.91050(12) 0.44493(12) 0.65420(12) 0.0140(2) Uani 1 1 d . . . H3 H 0.8551(16) 0.4121(15) 0.7505(17) 0.022(4) Uiso 1 1 d . . . C23 C 0.95753(12) 0.61619(12) 0.39824(11) 0.0147(2) Uani 1 1 d . . . H4 H 0.9248(15) 0.6950(15) 0.3272(15) 0.019(3) Uiso 1 1 d . . . C4 C 0.60515(14) 0.22537(12) 0.15039(13) 0.0170(2) Uani 1 1 d . . . H41 H 0.5044(14) 0.2006(13) 0.2201(14) 0.016(3) Uiso 1 1 d . . . O2 O 0.64496(9) 0.34335(8) 0.04191(9) 0.01634(15) Uani 1 1 d . . . N2 N 0.69298(12) 0.12054(10) 0.18063(11) 0.01871(19) Uani 1 1 d . . . C5 C 0.84818(15) 0.13270(15) 0.08720(18) 0.0268(3) Uani 1 1 d . . . H51 H 0.8693(17) 0.0603(17) 0.0456(17) 0.029(4) Uiso 1 1 d . . . H52 H 0.9060(18) 0.1270(17) 0.1440(18) 0.042(5) Uiso 1 1 d . . . H53 H 0.8703(19) 0.2184(19) 0.0080(19) 0.044(5) Uiso 1 1 d . . . C6 C 0.63659(19) -0.01397(14) 0.31125(15) 0.0289(3) Uani 1 1 d . . . H61 H 0.5340(18) -0.0109(17) 0.3655(17) 0.037(4) Uiso 1 1 d . . . H62 H 0.6889(17) -0.0210(16) 0.3784(17) 0.031(4) Uiso 1 1 d . . . H63 H 0.6561(17) -0.0964(18) 0.2770(17) 0.039(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.00998(9) 0.01218(8) 0.00953(7) -0.00339(6) -0.00347(6) 0.00325(6) S1 0.01086(13) 0.01311(11) 0.01028(11) -0.00536(9) -0.00298(10) 0.00205(10) O11 0.0139(4) 0.0250(4) 0.0093(3) -0.0050(3) -0.0017(3) 0.0037(3) O12 0.0132(4) 0.0157(3) 0.0128(3) -0.0042(3) -0.0059(3) 0.0020(3) O13 0.0228(4) 0.0153(4) 0.0255(4) -0.0109(3) -0.0087(4) 0.0010(3) C11 0.0101(5) 0.0145(4) 0.0106(4) -0.0052(3) -0.0027(4) 0.0010(4) C12 0.0133(5) 0.0188(5) 0.0093(4) -0.0045(4) -0.0027(4) 0.0029(4) C13 0.0136(5) 0.0177(5) 0.0112(4) -0.0040(4) -0.0048(4) 0.0032(4) C1 0.0168(6) 0.0174(5) 0.0182(5) -0.0047(4) -0.0062(5) 0.0033(4) O1 0.0147(4) 0.0162(4) 0.0165(4) -0.0044(3) -0.0063(3) 0.0056(3) N1 0.0203(5) 0.0151(4) 0.0233(5) -0.0022(4) -0.0097(4) 0.0051(4) C2 0.0505(11) 0.0296(8) 0.0341(8) 0.0011(6) -0.0230(8) 0.0126(8) C3 0.0247(7) 0.0189(6) 0.0377(8) -0.0122(5) -0.0075(6) 0.0082(5) Zn2 0.01022(9) 0.01210(8) 0.00901(7) -0.00339(6) -0.00312(6) 0.00323(6) S2 0.01038(12) 0.01215(11) 0.01031(11) -0.00469(9) -0.00247(10) 0.00124(9) O21 0.0140(4) 0.0149(3) 0.0137(3) -0.0040(3) -0.0064(3) 0.0020(3) O22 0.0139(4) 0.0205(4) 0.0098(3) -0.0046(3) -0.0015(3) 0.0023(3) O23 0.0192(4) 0.0150(4) 0.0238(4) -0.0102(3) -0.0063(3) 0.0007(3) C21 0.0096(5) 0.0138(4) 0.0110(4) -0.0052(3) -0.0026(4) 0.0015(4) C22 0.0121(5) 0.0168(5) 0.0097(4) -0.0032(4) -0.0019(4) 0.0017(4) C23 0.0141(5) 0.0157(5) 0.0112(4) -0.0029(4) -0.0031(4) 0.0026(4) C4 0.0177(6) 0.0153(5) 0.0164(5) -0.0059(4) -0.0051(4) 0.0051(4) O2 0.0146(4) 0.0151(3) 0.0166(4) -0.0032(3) -0.0056(3) 0.0044(3) N2 0.0228(5) 0.0144(4) 0.0181(4) -0.0047(3) -0.0083(4) 0.0059(4) C5 0.0183(6) 0.0229(6) 0.0398(8) -0.0106(6) -0.0131(6) 0.0080(5) C6 0.0459(10) 0.0169(5) 0.0202(6) -0.0038(5) -0.0116(6) 0.0075(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.0406(7) 2_666 ? Zn1 O1 2.0406(7) . ? Zn1 O21 2.1146(7) . ? Zn1 O21 2.1146(7) 2_666 ? Zn1 O11 2.1187(7) . ? Zn1 O11 2.1187(7) 2_666 ? S1 O13 1.4464(8) . ? S1 O11 1.4541(8) . ? S1 O12 1.4707(7) . ? S1 C11 1.7707(10) . ? O12 Zn2 2.1192(7) . ? C11 C13 1.3908(14) . ? C11 C12 1.3939(14) . ? C12 C13 1.3930(15) 2_765 ? C12 H1 0.860(14) . ? C13 C12 1.3930(15) 2_765 ? C13 H2 0.952(13) . ? C1 O1 1.2436(13) . ? C1 N1 1.3203(14) . ? C1 H11 0.952(13) . ? N1 C3 1.4537(18) . ? N1 C2 1.4599(17) . ? C2 H21 0.925(18) . ? C2 H22 0.93(2) . ? C2 H23 0.968(19) . ? C3 H31 0.934(16) . ? C3 H32 0.975(18) . ? C3 H33 0.921(17) . ? Zn2 O2 2.0639(7) 2_665 ? Zn2 O2 2.0639(7) . ? Zn2 O22 2.0849(7) 1_554 ? Zn2 O22 2.0849(7) 2_666 ? Zn2 O12 2.1192(7) 2_665 ? S2 O23 1.4482(8) . ? S2 O22 1.4584(8) . ? S2 O21 1.4656(7) . ? S2 C21 1.7705(10) . ? O22 Zn2 2.0849(7) 1_556 ? C21 C23 1.3915(14) . ? C21 C22 1.3933(14) . ? C22 C23 1.3925(15) 2_766 ? C22 H3 0.875(15) . ? C23 C22 1.3925(15) 2_766 ? C23 H4 0.981(14) . ? C4 O2 1.2458(13) . ? C4 N2 1.3228(14) . ? C4 H41 0.965(13) . ? N2 C5 1.4529(17) . ? N2 C6 1.4601(16) . ? C5 H51 0.930(15) . ? C5 H52 0.929(16) . ? C5 H53 0.906(18) . ? C6 H61 0.957(16) . ? C6 H62 0.971(15) . ? C6 H63 0.976(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 180.00(5) 2_666 . ? O1 Zn1 O21 92.29(3) 2_666 . ? O1 Zn1 O21 87.71(3) . . ? O1 Zn1 O21 87.71(3) 2_666 2_666 ? O1 Zn1 O21 92.29(3) . 2_666 ? O21 Zn1 O21 180.0 . 2_666 ? O1 Zn1 O11 86.05(3) 2_666 . ? O1 Zn1 O11 93.95(3) . . ? O21 Zn1 O11 89.37(3) . . ? O21 Zn1 O11 90.63(3) 2_666 . ? O1 Zn1 O11 93.95(3) 2_666 2_666 ? O1 Zn1 O11 86.05(3) . 2_666 ? O21 Zn1 O11 90.63(3) . 2_666 ? O21 Zn1 O11 89.37(3) 2_666 2_666 ? O11 Zn1 O11 180.000(1) . 2_666 ? O13 S1 O11 114.20(5) . . ? O13 S1 O12 111.38(5) . . ? O11 S1 O12 112.53(5) . . ? O13 S1 C11 106.05(5) . . ? O11 S1 C11 105.53(5) . . ? O12 S1 C11 106.43(4) . . ? S1 O11 Zn1 161.65(5) . . ? S1 O12 Zn2 132.81(4) . . ? C13 C11 C12 121.60(10) . . ? C13 C11 S1 118.89(8) . . ? C12 C11 S1 119.38(8) . . ? C13 C12 C11 119.04(10) 2_765 . ? C13 C12 H1 121.8(9) 2_765 . ? C11 C12 H1 119.2(9) . . ? C11 C13 C12 119.36(9) . 2_765 ? C11 C13 H2 120.8(8) . . ? C12 C13 H2 119.8(8) 2_765 . ? O1 C1 N1 123.24(11) . . ? O1 C1 H11 121.4(8) . . ? N1 C1 H11 115.3(8) . . ? C1 O1 Zn1 128.67(8) . . ? C1 N1 C3 121.24(10) . . ? C1 N1 C2 121.78(12) . . ? C3 N1 C2 116.92(12) . . ? N1 C2 H21 110.5(11) . . ? N1 C2 H22 110.0(12) . . ? H21 C2 H22 106.9(17) . . ? N1 C2 H23 107.7(11) . . ? H21 C2 H23 111.4(15) . . ? H22 C2 H23 110.3(16) . . ? N1 C3 H31 109.8(10) . . ? N1 C3 H32 108.5(10) . . ? H31 C3 H32 111.1(13) . . ? N1 C3 H33 108.4(10) . . ? H31 C3 H33 108.1(14) . . ? H32 C3 H33 110.9(14) . . ? O2 Zn2 O2 180.00(3) 2_665 . ? O2 Zn2 O22 94.85(3) 2_665 1_554 ? O2 Zn2 O22 85.15(3) . 1_554 ? O2 Zn2 O22 85.15(3) 2_665 2_666 ? O2 Zn2 O22 94.85(3) . 2_666 ? O22 Zn2 O22 180.00(4) 1_554 2_666 ? O2 Zn2 O12 87.69(3) 2_665 . ? O2 Zn2 O12 92.31(3) . . ? O22 Zn2 O12 90.99(3) 1_554 . ? O22 Zn2 O12 89.01(3) 2_666 . ? O2 Zn2 O12 92.31(3) 2_665 2_665 ? O2 Zn2 O12 87.69(3) . 2_665 ? O22 Zn2 O12 89.01(3) 1_554 2_665 ? O22 Zn2 O12 90.99(3) 2_666 2_665 ? O12 Zn2 O12 180.00(4) . 2_665 ? O23 S2 O22 114.00(5) . . ? O23 S2 O21 111.96(5) . . ? O22 S2 O21 112.43(5) . . ? O23 S2 C21 106.51(5) . . ? O22 S2 C21 104.62(5) . . ? O21 S2 C21 106.56(4) . . ? S2 O21 Zn1 132.81(4) . . ? S2 O22 Zn2 153.50(5) . 1_556 ? C23 C21 C22 121.70(9) . . ? C23 C21 S2 118.74(8) . . ? C22 C21 S2 119.54(8) . . ? C23 C22 C21 118.91(10) 2_766 . ? C23 C22 H3 120.3(9) 2_766 . ? C21 C22 H3 120.7(9) . . ? C21 C23 C22 119.39(9) . 2_766 ? C21 C23 H4 120.3(8) . . ? C22 C23 H4 120.3(8) 2_766 . ? O2 C4 N2 124.59(12) . . ? O2 C4 H41 122.4(7) . . ? N2 C4 H41 113.0(7) . . ? C4 O2 Zn2 122.23(8) . . ? C4 N2 C5 122.31(10) . . ? C4 N2 C6 120.74(11) . . ? C5 N2 C6 116.95(10) . . ? N2 C5 H51 110.8(10) . . ? N2 C5 H52 110.3(10) . . ? H51 C5 H52 109.9(13) . . ? N2 C5 H53 109.5(11) . . ? H51 C5 H53 106.2(14) . . ? H52 C5 H53 110.0(14) . . ? N2 C6 H61 110.5(9) . . ? N2 C6 H62 107.5(9) . . ? H61 C6 H62 107.9(12) . . ? N2 C6 H63 109.2(9) . . ? H61 C6 H63 112.2(13) . . ? H62 C6 H63 109.6(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O13 S1 O11 Zn1 28.25(18) . . . . ? O12 S1 O11 Zn1 -100.01(16) . . . . ? C11 S1 O11 Zn1 144.32(16) . . . . ? O1 Zn1 O11 S1 -140.88(17) 2_666 . . . ? O1 Zn1 O11 S1 39.12(17) . . . . ? O21 Zn1 O11 S1 -48.55(16) . . . . ? O21 Zn1 O11 S1 131.45(16) 2_666 . . . ? O11 Zn1 O11 S1 148(100) 2_666 . . . ? O13 S1 O12 Zn2 -171.42(6) . . . . ? O11 S1 O12 Zn2 -41.70(7) . . . . ? C11 S1 O12 Zn2 73.43(7) . . . . ? O13 S1 C11 C13 -74.54(9) . . . . ? O11 S1 C11 C13 163.95(8) . . . . ? O12 S1 C11 C13 44.18(10) . . . . ? O13 S1 C11 C12 101.26(9) . . . . ? O11 S1 C11 C12 -20.25(10) . . . . ? O12 S1 C11 C12 -140.02(9) . . . . ? C13 C11 C12 C13 0.38(18) . . . 2_765 ? S1 C11 C12 C13 -175.30(9) . . . 2_765 ? C12 C11 C13 C12 -0.38(18) . . . 2_765 ? S1 C11 C13 C12 175.32(9) . . . 2_765 ? N1 C1 O1 Zn1 -170.91(8) . . . . ? O1 Zn1 O1 C1 -88(100) 2_666 . . . ? O21 Zn1 O1 C1 88.84(10) . . . . ? O21 Zn1 O1 C1 -91.16(10) 2_666 . . . ? O11 Zn1 O1 C1 -0.36(10) . . . . ? O11 Zn1 O1 C1 179.64(10) 2_666 . . . ? O1 C1 N1 C3 -1.48(19) . . . . ? O1 C1 N1 C2 -178.78(14) . . . . ? S1 O12 Zn2 O2 141.27(6) . . . 2_665 ? S1 O12 Zn2 O2 -38.73(6) . . . . ? S1 O12 Zn2 O22 -123.91(6) . . . 1_554 ? S1 O12 Zn2 O22 56.09(6) . . . 2_666 ? S1 O12 Zn2 O12 -164(100) . . . 2_665 ? O23 S2 O21 Zn1 -168.55(6) . . . . ? O22 S2 O21 Zn1 -38.69(7) . . . . ? C21 S2 O21 Zn1 75.38(7) . . . . ? O1 Zn1 O21 S2 -40.37(6) 2_666 . . . ? O1 Zn1 O21 S2 139.63(6) . . . . ? O21 Zn1 O21 S2 124(100) 2_666 . . . ? O11 Zn1 O21 S2 -126.39(6) . . . . ? O11 Zn1 O21 S2 53.61(6) 2_666 . . . ? O23 S2 O22 Zn2 26.01(13) . . . 1_556 ? O21 S2 O22 Zn2 -102.79(11) . . . 1_556 ? C21 S2 O22 Zn2 141.96(11) . . . 1_556 ? O23 S2 C21 C23 -69.11(9) . . . . ? O22 S2 C21 C23 169.84(8) . . . . ? O21 S2 C21 C23 50.56(10) . . . . ? O23 S2 C21 C22 108.92(9) . . . . ? O22 S2 C21 C22 -12.13(10) . . . . ? O21 S2 C21 C22 -131.41(9) . . . . ? C23 C21 C22 C23 0.44(18) . . . 2_766 ? S2 C21 C22 C23 -177.53(8) . . . 2_766 ? C22 C21 C23 C22 -0.44(18) . . . 2_766 ? S2 C21 C23 C22 177.54(8) . . . 2_766 ? N2 C4 O2 Zn2 178.78(8) . . . . ? O2 Zn2 O2 C4 -77(100) 2_665 . . . ? O22 Zn2 O2 C4 -146.28(9) 1_554 . . . ? O22 Zn2 O2 C4 33.72(9) 2_666 . . . ? O12 Zn2 O2 C4 122.92(9) . . . . ? O12 Zn2 O2 C4 -57.08(9) 2_665 . . . ? O2 C4 N2 C5 -0.49(18) . . . . ? O2 C4 N2 C6 179.57(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.635 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.097 data_c:\cz12\cz12_neu\cz12 _database_code_depnum_ccdc_archive 'CCDC 763638' #TrackingRef 'CZ12.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 Cl4 N4 O10 S2 Zn' _chemical_formula_weight 731.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0518(12) _cell_length_b 9.8960(10) _cell_length_c 8.3148(11) _cell_angle_alpha 91.409(16) _cell_angle_beta 106.723(16) _cell_angle_gamma 90.440(16) _cell_volume 713.01(15) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11246 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3226 _reflns_number_gt 2699 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3226 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0501 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 1.755 _refine_ls_restrained_S_all 1.755 _refine_ls_shift/su_max 1.273 _refine_ls_shift/su_mean 0.321 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.5000 0.01625(8) Uani 1 2 d S . . S5 S 0.75254(4) 0.76343(5) 0.62601(5) 0.01732(10) Uani 1 1 d . . . Cl1 Cl 0.50810(5) 0.83784(5) 0.81684(5) 0.02696(11) Uani 1 1 d . . . Cl2 Cl 0.27259(6) 1.05158(7) 0.71297(7) 0.04387(16) Uani 1 1 d . . . C6 C 0.50565(18) 0.92591(18) 0.6395(2) 0.0167(3) Uani 1 1 d . . . O8 O 0.66397(13) 0.34963(14) 0.59619(15) 0.0237(3) Uani 1 1 d . . . N8 N 0.78719(15) 0.19912(17) 0.78809(18) 0.0207(3) Uani 1 1 d . . . O9 O 0.66022(13) 0.64522(13) 0.64166(14) 0.0199(3) Uani 1 1 d . . . O10 O 0.58588(13) 0.52121(14) 0.29790(15) 0.0230(3) Uani 1 1 d . . . O11 O 0.84281(13) 0.81684(14) 0.78745(16) 0.0267(3) Uani 1 1 d . . . O12 O 0.83693(14) 0.74124(14) 0.50556(17) 0.0281(3) Uani 1 1 d . . . C9 C 0.67749(19) 0.28612(19) 0.7260(2) 0.0197(4) Uani 1 1 d . . . H1 H 0.601(2) 0.300(2) 0.789(3) 0.025(5) Uiso 1 1 d . . . C7 C 0.39674(18) 1.02756(18) 0.5915(2) 0.0174(3) Uani 1 1 d . . . C8 C 0.61121(17) 0.89507(18) 0.5495(2) 0.0152(3) Uani 1 1 d . . . N9 N 0.78606(15) 0.51042(16) 0.18660(17) 0.0199(3) Uani 1 1 d . . . C10 C 0.71749(19) 0.4838(2) 0.3025(2) 0.0236(4) Uani 1 1 d . . . H2 H 0.784(2) 0.437(2) 0.402(3) 0.022(5) Uiso 1 1 d . . . C11 C 0.7949(2) 0.1287(3) 0.9433(2) 0.0317(5) Uani 1 1 d . . . H3 H 0.786(3) 0.030(3) 0.924(3) 0.032(6) Uiso 1 1 d . . . H6 H 0.900(3) 0.157(3) 1.033(3) 0.051(7) Uiso 1 1 d . . . H9 H 0.708(3) 0.157(3) 0.971(3) 0.051(7) Uiso 1 1 d . . . C12 C 0.7131(2) 0.5950(3) 0.0473(3) 0.0336(5) Uani 1 1 d . . . H7 H 0.784(4) 0.653(4) 0.017(4) 0.077(10) Uiso 1 1 d . . . H11 H 0.717(5) 0.547(5) -0.041(6) 0.135(17) Uiso 1 1 d . . . H12 H 0.614(5) 0.624(4) 0.034(5) 0.104(14) Uiso 1 1 d . . . C13 C 0.9059(2) 0.1660(3) 0.7068(3) 0.0330(5) Uani 1 1 d . . . H4 H 0.913(3) 0.070(3) 0.699(3) 0.034(6) Uiso 1 1 d . . . H10 H 1.007(4) 0.193(3) 0.785(4) 0.064(9) Uiso 1 1 d . . . H14 H 0.881(3) 0.209(3) 0.606(4) 0.063(9) Uiso 1 1 d . . . C14 C 0.9415(2) 0.4635(3) 0.2018(3) 0.0388(5) Uani 1 1 d . . . H5 H 0.971(3) 0.422(3) 0.297(4) 0.056(8) Uiso 1 1 d . . . H8 H 0.941(3) 0.413(3) 0.095(4) 0.069(9) Uiso 1 1 d . . . H13 H 1.013(3) 0.541(3) 0.208(4) 0.058(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01651(13) 0.01737(17) 0.01670(14) 0.00549(11) 0.00715(10) 0.00481(11) S5 0.01470(17) 0.0153(2) 0.0220(2) 0.00509(16) 0.00496(15) 0.00579(16) Cl1 0.0317(2) 0.0315(3) 0.0232(2) 0.01582(19) 0.01524(17) 0.01578(19) Cl2 0.0508(3) 0.0555(4) 0.0422(3) 0.0304(3) 0.0370(2) 0.0389(3) C6 0.0196(7) 0.0157(9) 0.0154(7) 0.0047(6) 0.0056(6) 0.0028(7) O8 0.0233(6) 0.0233(8) 0.0262(6) 0.0074(5) 0.0092(5) 0.0063(5) N8 0.0178(6) 0.0207(9) 0.0228(7) 0.0051(6) 0.0040(5) 0.0047(6) O9 0.0222(5) 0.0161(7) 0.0207(6) 0.0042(5) 0.0046(4) 0.0029(5) O10 0.0210(5) 0.0284(8) 0.0216(6) 0.0045(5) 0.0090(5) 0.0043(5) O11 0.0227(6) 0.0206(8) 0.0295(7) 0.0022(5) -0.0044(5) 0.0045(5) O12 0.0282(6) 0.0254(8) 0.0379(7) 0.0131(6) 0.0194(5) 0.0146(6) C9 0.0181(7) 0.0202(10) 0.0205(8) 0.0014(7) 0.0047(6) -0.0005(7) C7 0.0185(7) 0.0190(10) 0.0173(7) 0.0031(7) 0.0088(6) 0.0057(7) C8 0.0139(7) 0.0137(9) 0.0178(7) 0.0027(6) 0.0042(5) 0.0038(6) N9 0.0226(7) 0.0205(9) 0.0194(7) 0.0055(6) 0.0100(5) 0.0070(6) C10 0.0255(8) 0.0265(12) 0.0201(8) 0.0082(8) 0.0079(6) 0.0078(8) C11 0.0358(11) 0.0315(14) 0.0262(10) 0.0097(9) 0.0054(8) 0.0084(9) C12 0.0292(10) 0.0465(15) 0.0254(10) 0.0177(9) 0.0068(8) 0.0061(9) C13 0.0260(10) 0.0260(13) 0.0520(14) 0.0062(10) 0.0184(9) 0.0092(9) C14 0.0342(11) 0.0449(16) 0.0471(13) 0.0210(11) 0.0249(9) 0.0220(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 Zn1 O10 2.0588(11) . ? Zn1 O10 2.0588(11) 2_666 ? Zn1 O9 2.1113(13) . ? Zn1 O9 2.1113(13) 2_666 ? Zn1 O8 2.1133(13) 2_666 ? Zn1 O8 2.1133(13) . ? S5 O12 1.4377(13) . ? S5 O11 1.4409(13) . ? S5 O9 1.4625(12) . ? S5 C8 1.8265(17) . ? Cl1 C6 1.7259(16) . ? Cl2 C7 1.7275(15) . ? C6 C8 1.404(2) . ? C6 C7 1.397(2) . ? O8 C9 1.238(2) . ? N8 C9 1.317(2) . ? N8 C13 1.460(2) . ? N8 C11 1.466(2) . ? O10 C10 1.241(2) . ? C7 C8 1.401(2) 2_676 ? C8 C7 1.401(2) 2_676 ? N9 C10 1.318(2) . ? N9 C12 1.447(2) . ? N9 C14 1.457(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 Zn1 O10 180.0 . 2_666 ? O10 Zn1 O9 90.93(5) . . ? O10 Zn1 O9 89.07(5) 2_666 . ? O10 Zn1 O9 89.07(5) . 2_666 ? O10 Zn1 O9 90.93(5) 2_666 2_666 ? O9 Zn1 O9 180.0 . 2_666 ? O10 Zn1 O8 89.70(5) . 2_666 ? O10 Zn1 O8 90.30(5) 2_666 2_666 ? O9 Zn1 O8 91.73(5) . 2_666 ? O9 Zn1 O8 88.27(5) 2_666 2_666 ? O10 Zn1 O8 90.30(5) . . ? O10 Zn1 O8 89.70(5) 2_666 . ? O9 Zn1 O8 88.27(5) . . ? O9 Zn1 O8 91.73(5) 2_666 . ? O8 Zn1 O8 180.0 2_666 . ? O12 S5 O11 115.06(8) . . ? O12 S5 O9 112.48(8) . . ? O11 S5 O9 111.92(7) . . ? O12 S5 C8 108.57(7) . . ? O11 S5 C8 103.28(8) . . ? O9 S5 C8 104.49(7) . . ? C8 C6 C7 122.27(14) . . ? C8 C6 Cl1 120.11(13) . . ? C7 C6 Cl1 117.62(12) . . ? C9 O8 Zn1 126.36(12) . . ? C9 N8 C13 122.50(16) . . ? C9 N8 C11 121.15(15) . . ? C13 N8 C11 116.34(17) . . ? S5 O9 Zn1 142.79(7) . . ? C10 O10 Zn1 121.57(11) . . ? O8 C9 N8 124.76(16) . . ? C8 C7 C6 121.11(14) 2_676 . ? C8 C7 Cl2 122.06(13) 2_676 . ? C6 C7 Cl2 116.83(12) . . ? C7 C8 C6 116.62(15) 2_676 . ? C7 C8 S5 124.48(12) 2_676 . ? C6 C8 S5 118.86(12) . . ? C10 N9 C12 120.76(15) . . ? C10 N9 C14 120.86(16) . . ? C12 N9 C14 118.25(16) . . ? O10 C10 N9 124.21(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O10 Zn1 O8 C9 -178.89(15) . . . . ? O10 Zn1 O8 C9 1.11(15) 2_666 . . . ? O9 Zn1 O8 C9 90.20(15) . . . . ? O9 Zn1 O8 C9 -89.80(15) 2_666 . . . ? O8 Zn1 O8 C9 -85(100) 2_666 . . . ? O12 S5 O9 Zn1 -48.80(15) . . . . ? O11 S5 O9 Zn1 179.85(11) . . . . ? C8 S5 O9 Zn1 68.77(14) . . . . ? O10 Zn1 O9 S5 26.69(13) . . . . ? O10 Zn1 O9 S5 -153.31(13) 2_666 . . . ? O9 Zn1 O9 S5 117(100) 2_666 . . . ? O8 Zn1 O9 S5 -63.04(13) 2_666 . . . ? O8 Zn1 O9 S5 116.96(13) . . . . ? O10 Zn1 O10 C10 -42(100) 2_666 . . . ? O9 Zn1 O10 C10 67.79(15) . . . . ? O9 Zn1 O10 C10 -112.21(15) 2_666 . . . ? O8 Zn1 O10 C10 159.51(16) 2_666 . . . ? O8 Zn1 O10 C10 -20.49(16) . . . . ? Zn1 O8 C9 N8 -175.47(13) . . . . ? C13 N8 C9 O8 -1.1(3) . . . . ? C11 N8 C9 O8 179.71(18) . . . . ? C8 C6 C7 C8 -0.5(3) . . . 2_676 ? Cl1 C6 C7 C8 179.07(13) . . . 2_676 ? C8 C6 C7 Cl2 178.92(14) . . . . ? Cl1 C6 C7 Cl2 -1.46(19) . . . . ? C7 C6 C8 C7 0.5(3) . . . 2_676 ? Cl1 C6 C8 C7 -179.09(13) . . . 2_676 ? C7 C6 C8 S5 178.32(13) . . . . ? Cl1 C6 C8 S5 -1.3(2) . . . . ? O12 S5 C8 C7 -7.88(17) . . . 2_676 ? O11 S5 C8 C7 114.69(15) . . . 2_676 ? O9 S5 C8 C7 -128.11(15) . . . 2_676 ? O12 S5 C8 C6 174.50(13) . . . . ? O11 S5 C8 C6 -62.92(15) . . . . ? O9 S5 C8 C6 54.28(15) . . . . ? Zn1 O10 C10 N9 -170.75(14) . . . . ? C12 N9 C10 O10 4.0(3) . . . . ? C14 N9 C10 O10 179.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.498 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.061 data_e:\cz29\cz29 _database_code_depnum_ccdc_archive 'CCDC 763639' #TrackingRef '337_web_deposit_cif_file_0_ChristinaZitzer_1264610327.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H0 F4 N4 O10 S2 Zn2' _chemical_formula_weight 703.08 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' 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' S S 0.1246 0.1234 '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 ? _symmetry_space_group_name_H-M ? 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 8.8901(3) _cell_length_b 9.6891(3) _cell_length_c 16.3307(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.524(2) _cell_angle_gamma 90.00 _cell_volume 1348.58(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.017 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25846 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 35.19 _reflns_number_total 5836 _reflns_number_gt 3269 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0412P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5836 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.880 _refine_ls_shift/su_max 0.007 _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 Zn1 Zn 0.5000 0.0000 0.0000 0.01603(8) Uani 1 2 d S . . S1 S 0.32132(6) 0.25785(5) 0.07180(3) 0.01792(10) Uani 1 1 d . . . O1 O 0.17068(16) 0.23842(14) 0.01102(9) 0.0277(3) Uani 1 1 d . . . O2 O 0.31749(18) 0.31011(13) 0.15397(9) 0.0267(3) Uani 1 1 d . . . O3 O 0.42617(16) 0.13962(12) 0.08033(8) 0.0186(3) Uani 1 1 d . . . C1 C 0.4182(2) 0.39229(17) 0.02922(11) 0.0166(3) Uani 1 1 d . . . C2 C 0.5671(2) 0.43499(19) 0.07452(12) 0.0208(4) Uani 1 1 d . . . F1 F 0.64088(15) 0.37296(13) 0.14886(8) 0.0365(3) Uani 1 1 d . . . C3 C 0.3529(2) 0.46100(19) -0.04711(12) 0.0201(4) Uani 1 1 d . . . F2 F 0.20908(15) 0.43068(14) -0.09713(8) 0.0387(3) Uani 1 1 d . . . O4 O 0.69079(16) -0.04308(13) 0.10388(8) 0.0213(3) Uani 1 1 d . . . C4 C 0.8266(2) -0.0067(2) 0.10795(12) 0.0212(4) Uani 1 1 d . . . H41 H 0.849(3) 0.051(2) 0.0635(15) 0.034(6) Uiso 1 1 d . . . N1 N 0.95227(19) -0.03894(16) 0.17054(10) 0.0197(3) Uani 1 1 d . . . C5 C 1.1077(3) 0.0076(3) 0.17011(16) 0.0306(5) Uani 1 1 d . . . H51 H 1.154(3) 0.072(2) 0.2233(16) 0.044(7) Uiso 1 1 d . . . H52 H 1.103(4) 0.063(3) 0.131(2) 0.062(9) Uiso 1 1 d . . . H53 H 1.179(3) -0.072(3) 0.1743(17) 0.055(8) Uiso 1 1 d . . . C6 C 0.9413(3) -0.1284(3) 0.23991(15) 0.0335(5) Uani 1 1 d . . . H61 H 0.832(4) -0.151(3) 0.2422(17) 0.058(8) Uiso 1 1 d . . . H62 H 1.002(3) -0.205(3) 0.2443(15) 0.052(8) Uiso 1 1 d . . . H63 H 0.984(4) -0.081(3) 0.300(2) 0.090(11) Uiso 1 1 d . . . O5 O 0.37284(16) -0.15704(13) 0.03799(8) 0.0212(3) Uani 1 1 d . . . C7 C 0.4096(2) -0.21372(18) 0.10944(12) 0.0178(4) Uani 1 1 d . . . H71 H 0.508(2) -0.1956(19) 0.1515(12) 0.018(5) Uiso 1 1 d . . . N2 N 0.32158(19) -0.30629(15) 0.13302(10) 0.0193(3) Uani 1 1 d . . . C8 C 0.3707(3) -0.3672(2) 0.21876(14) 0.0305(5) Uani 1 1 d . . . H81 H 0.466(3) -0.332(2) 0.2482(15) 0.038(7) Uiso 1 1 d . . . H82 H 0.288(3) -0.341(2) 0.2475(17) 0.043(7) Uiso 1 1 d . . . H83 H 0.385(3) -0.471(2) 0.2109(15) 0.040(7) Uiso 1 1 d . . . C9 C 0.1696(3) -0.3468(2) 0.07821(15) 0.0270(5) Uani 1 1 d . . . H91 H 0.157(3) -0.456(2) 0.0745(14) 0.027(6) Uiso 1 1 d . . . H92 H 0.091(3) -0.319(2) 0.0941(16) 0.045(8) Uiso 1 1 d . . . H93 H 0.159(3) -0.326(3) 0.0199(18) 0.055(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01654(15) 0.01674(14) 0.01464(14) 0.00099(12) 0.00415(11) -0.00036(12) S1 0.0186(2) 0.0168(2) 0.0201(2) 0.00165(16) 0.00836(18) -0.00004(17) O1 0.0174(7) 0.0270(7) 0.0361(8) 0.0075(6) 0.0036(6) -0.0028(6) O2 0.0383(9) 0.0221(7) 0.0268(8) -0.0009(6) 0.0206(7) 0.0015(6) O3 0.0227(7) 0.0167(6) 0.0169(6) 0.0004(5) 0.0063(5) 0.0021(5) C1 0.0168(9) 0.0170(8) 0.0171(8) -0.0003(6) 0.0062(7) -0.0001(7) C2 0.0212(10) 0.0231(9) 0.0162(9) 0.0060(7) 0.0020(7) 0.0004(7) F1 0.0294(7) 0.0446(8) 0.0265(7) 0.0202(6) -0.0065(5) -0.0114(6) C3 0.0162(9) 0.0224(9) 0.0194(9) 0.0013(7) 0.0012(7) -0.0028(7) F2 0.0254(7) 0.0474(8) 0.0323(7) 0.0174(6) -0.0094(6) -0.0171(6) O4 0.0182(7) 0.0261(7) 0.0192(7) 0.0014(5) 0.0048(6) -0.0011(5) C4 0.0207(9) 0.0241(9) 0.0181(8) 0.0024(8) 0.0042(7) -0.0031(8) N1 0.0169(8) 0.0241(8) 0.0178(8) 0.0011(6) 0.0046(6) -0.0011(6) C5 0.0209(10) 0.0362(12) 0.0340(12) 0.0076(11) 0.0067(9) -0.0054(10) C6 0.0243(13) 0.0495(15) 0.0266(12) 0.0171(10) 0.0067(10) 0.0025(11) O5 0.0214(7) 0.0222(7) 0.0197(7) 0.0034(5) 0.0055(6) -0.0016(5) C7 0.0191(10) 0.0163(8) 0.0180(9) -0.0023(7) 0.0052(8) -0.0002(7) N2 0.0218(8) 0.0192(7) 0.0169(8) 0.0001(6) 0.0058(6) -0.0023(6) C8 0.0459(15) 0.0270(11) 0.0180(10) 0.0017(8) 0.0082(10) -0.0076(10) C9 0.0205(11) 0.0291(11) 0.0312(12) 0.0025(9) 0.0071(9) -0.0044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.0718(13) 3_655 ? Zn1 O4 2.0718(13) . ? Zn1 O5 2.0922(13) 3_655 ? Zn1 O5 2.0922(13) . ? Zn1 O3 2.1146(12) 3_655 ? Zn1 O3 2.1146(12) . ? S1 O1 1.4345(15) . ? S1 O2 1.4438(14) . ? S1 O3 1.4583(13) . ? S1 C1 1.8062(18) . ? C1 C2 1.384(3) . ? C1 C3 1.386(2) . ? C2 F1 1.346(2) . ? C2 C3 1.379(3) 3_665 ? C3 F2 1.339(2) . ? C3 C2 1.379(3) 3_665 ? O4 C4 1.241(2) . ? C4 N1 1.320(2) . ? N1 C6 1.451(3) . ? N1 C5 1.455(3) . ? O5 C7 1.246(2) . ? C7 N2 1.318(2) . ? N2 C9 1.447(3) . ? N2 C8 1.467(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O4 180.00(9) 3_655 . ? O4 Zn1 O5 89.78(5) 3_655 3_655 ? O4 Zn1 O5 90.22(5) . 3_655 ? O4 Zn1 O5 90.22(5) 3_655 . ? O4 Zn1 O5 89.78(5) . . ? O5 Zn1 O5 180.00(8) 3_655 . ? O4 Zn1 O3 86.97(5) 3_655 3_655 ? O4 Zn1 O3 93.03(5) . 3_655 ? O5 Zn1 O3 89.55(5) 3_655 3_655 ? O5 Zn1 O3 90.45(5) . 3_655 ? O4 Zn1 O3 93.03(5) 3_655 . ? O4 Zn1 O3 86.97(5) . . ? O5 Zn1 O3 90.45(5) 3_655 . ? O5 Zn1 O3 89.55(5) . . ? O3 Zn1 O3 180.00(7) 3_655 . ? O1 S1 O2 115.14(9) . . ? O1 S1 O3 114.11(8) . . ? O2 S1 O3 111.72(8) . . ? O1 S1 C1 106.37(8) . . ? O2 S1 C1 104.17(8) . . ? O3 S1 C1 103.98(8) . . ? S1 O3 Zn1 138.25(8) . . ? C2 C1 C3 115.43(16) . . ? C2 C1 S1 119.89(13) . . ? C3 C1 S1 124.67(14) . . ? F1 C2 C3 117.07(17) . 3_665 ? F1 C2 C1 119.69(16) . . ? C3 C2 C1 123.24(16) 3_665 . ? F2 C3 C2 116.94(16) . 3_665 ? F2 C3 C1 121.73(17) . . ? C2 C3 C1 121.33(17) 3_665 . ? C4 O4 Zn1 122.95(12) . . ? O4 C4 N1 124.80(18) . . ? C4 N1 C6 121.04(18) . . ? C4 N1 C5 121.26(17) . . ? C6 N1 C5 117.62(18) . . ? C7 O5 Zn1 125.33(12) . . ? O5 C7 N2 123.67(18) . . ? C7 N2 C9 122.11(17) . . ? C7 N2 C8 120.84(18) . . ? C9 N2 C8 116.96(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 O3 Zn1 45.70(15) . . . . ? O2 S1 O3 Zn1 178.50(11) . . . . ? C1 S1 O3 Zn1 -69.75(13) . . . . ? O4 Zn1 O3 S1 -19.19(13) 3_655 . . . ? O4 Zn1 O3 S1 160.81(13) . . . . ? O5 Zn1 O3 S1 70.62(12) 3_655 . . . ? O5 Zn1 O3 S1 -109.38(12) . . . . ? O3 Zn1 O3 S1 -147(100) 3_655 . . . ? O1 S1 C1 C2 179.55(15) . . . . ? O2 S1 C1 C2 57.48(17) . . . . ? O3 S1 C1 C2 -59.66(17) . . . . ? O1 S1 C1 C3 0.83(19) . . . . ? O2 S1 C1 C3 -121.23(17) . . . . ? O3 S1 C1 C3 121.62(16) . . . . ? C3 C1 C2 F1 -179.10(17) . . . . ? S1 C1 C2 F1 2.1(3) . . . . ? C3 C1 C2 C3 0.3(3) . . . 3_665 ? S1 C1 C2 C3 -178.52(16) . . . 3_665 ? C2 C1 C3 F2 -179.61(18) . . . . ? S1 C1 C3 F2 -0.8(3) . . . . ? C2 C1 C3 C2 -0.3(3) . . . 3_665 ? S1 C1 C3 C2 178.46(15) . . . 3_665 ? O4 Zn1 O4 C4 161(100) 3_655 . . . ? O5 Zn1 O4 C4 -19.28(15) 3_655 . . . ? O5 Zn1 O4 C4 160.72(15) . . . . ? O3 Zn1 O4 C4 70.28(15) 3_655 . . . ? O3 Zn1 O4 C4 -109.72(15) . . . . ? Zn1 O4 C4 N1 -175.83(14) . . . . ? O4 C4 N1 C6 3.1(3) . . . . ? O4 C4 N1 C5 179.7(2) . . . . ? O4 Zn1 O5 C7 -165.22(14) 3_655 . . . ? O4 Zn1 O5 C7 14.78(14) . . . . ? O5 Zn1 O5 C7 7(100) 3_655 . . . ? O3 Zn1 O5 C7 107.81(14) 3_655 . . . ? O3 Zn1 O5 C7 -72.19(14) . . . . ? Zn1 O5 C7 N2 175.57(13) . . . . ? O5 C7 N2 C9 -2.4(3) . . . . ? O5 C7 N2 C8 -178.91(18) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 35.19 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.499 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.120 data_d:\struktur\cuclpbds\cuclpbds _database_code_depnum_ccdc_archive 'CCDC 776934' #TrackingRef '1154_web_deposit_cif_file_0_ChristinaZitzer_1273683984.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Cl4 Cu O10 S2' _chemical_formula_sum 'C6 H8 Cl4 Cu O10 S2' _chemical_formula_weight 509.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 7.2127(2) _cell_length_b 21.4781(6) _cell_length_c 9.7942(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1517.27(8) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9927 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 34.99 _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 2.466 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5472 _exptl_absorpt_correction_T_max 0.8049 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26926 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 35.07 _reflns_number_total 3403 _reflns_number_gt 3046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+1.7849P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3403 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0736 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 1.0000 0.01089(6) Uani 1 2 d S . . O1 O 0.15072(14) 0.52507(5) 0.84541(10) 0.01375(16) Uani 1 1 d . . . H1 H 0.244(4) 0.5433(11) 0.860(3) 0.027(6) Uiso 1 1 d . . . H2 H 0.100(4) 0.5429(12) 0.789(3) 0.039(7) Uiso 1 1 d . . . O2 O 0.14377(15) 0.55250(5) 1.12455(10) 0.01556(17) Uani 1 1 d . . . H3 H 0.251(4) 0.5564(11) 1.120(2) 0.022(5) Uiso 1 1 d . . . H4 H 0.110(4) 0.5579(12) 1.197(3) 0.039(7) Uiso 1 1 d . . . S1 S 0.40486(4) 0.399579(13) 1.01581(3) 0.01002(6) Uani 1 1 d . . . O3 O 0.21023(13) 0.41208(5) 1.03611(11) 0.01546(17) Uani 1 1 d . . . O4 O 0.48219(14) 0.42355(5) 0.88815(10) 0.01514(17) Uani 1 1 d . . . O5 O 0.51610(14) 0.41866(5) 1.13342(10) 0.01452(17) Uani 1 1 d . . . C1 C 0.42734(17) 0.31590(6) 1.00337(12) 0.01108(19) Uani 1 1 d . . . C2 C 0.29518(18) 0.28257(6) 0.92717(13) 0.01276(19) Uani 1 1 d . . . Cl1 Cl 0.13952(6) 0.320509(15) 0.82391(4) 0.02313(8) Uani 1 1 d . . . C3 C 0.57550(18) 0.28275(6) 1.06127(14) 0.0149(2) Uani 1 1 d . . . Cl2 Cl 0.76971(6) 0.319340(17) 1.12444(6) 0.03482(12) 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 Cu1 0.01064(10) 0.01305(10) 0.00897(9) 0.00022(6) -0.00005(6) -0.00180(7) O1 0.0126(4) 0.0169(4) 0.0118(4) 0.0029(3) -0.0004(3) -0.0019(3) O2 0.0128(4) 0.0212(4) 0.0127(4) -0.0036(3) -0.0001(3) -0.0030(3) S1 0.01012(12) 0.00871(11) 0.01123(11) -0.00010(8) 0.00007(9) 0.00045(9) O3 0.0110(4) 0.0139(4) 0.0215(4) -0.0004(3) 0.0015(3) 0.0027(3) O4 0.0157(4) 0.0165(4) 0.0133(4) 0.0037(3) 0.0011(3) -0.0011(3) O5 0.0142(4) 0.0152(4) 0.0141(4) -0.0044(3) -0.0018(3) -0.0003(3) C1 0.0108(5) 0.0096(4) 0.0129(5) 0.0000(3) -0.0016(3) 0.0004(3) C2 0.0139(5) 0.0110(4) 0.0133(4) 0.0006(3) -0.0044(4) 0.0007(4) Cl1 0.02717(17) 0.01437(13) 0.02785(17) 0.00067(11) -0.01748(13) 0.00300(11) C3 0.0122(5) 0.0102(4) 0.0224(5) -0.0004(4) -0.0055(4) -0.0005(4) Cl2 0.02041(17) 0.01267(14) 0.0714(3) -0.00398(16) -0.02439(19) -0.00020(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9402(9) 5_567 ? Cu1 O1 1.9402(9) . ? Cu1 O2 1.9582(10) . ? Cu1 O2 1.9582(10) 5_567 ? Cu1 O3 2.4475(10) . ? Cu1 O3 2.4475(10) 5_567 ? O1 H1 0.79(3) . ? O1 H2 0.76(3) . ? O2 H3 0.78(3) . ? O2 H4 0.76(3) . ? S1 O3 1.4430(10) . ? S1 O5 1.4624(10) . ? S1 O4 1.4627(10) . ? S1 C1 1.8088(12) . ? C1 C3 1.4037(17) . ? C1 C2 1.4064(17) . ? C2 C2 1.399(2) 8_565 ? C2 Cl1 1.7169(12) . ? C3 C3 1.407(2) 8_565 ? C3 Cl2 1.7212(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0 5_567 . ? O1 Cu1 O2 88.30(4) 5_567 . ? O1 Cu1 O2 91.70(4) . . ? O1 Cu1 O2 91.70(4) 5_567 5_567 ? O1 Cu1 O2 88.30(4) . 5_567 ? O2 Cu1 O2 180.00(5) . 5_567 ? O1 Cu1 O3 91.16(4) 5_567 . ? O1 Cu1 O3 88.84(4) . . ? O2 Cu1 O3 91.50(4) . . ? O2 Cu1 O3 88.50(4) 5_567 . ? O1 Cu1 O3 88.84(4) 5_567 5_567 ? O1 Cu1 O3 91.16(4) . 5_567 ? O2 Cu1 O3 88.50(4) . 5_567 ? O2 Cu1 O3 91.50(4) 5_567 5_567 ? O3 Cu1 O3 180.0 . 5_567 ? Cu1 O1 H1 118.5(18) . . ? Cu1 O1 H2 116(2) . . ? H1 O1 H2 106(3) . . ? Cu1 O2 H3 123.3(18) . . ? Cu1 O2 H4 120(2) . . ? H3 O2 H4 111(3) . . ? O3 S1 O5 111.91(6) . . ? O3 S1 O4 115.04(6) . . ? O5 S1 O4 111.43(6) . . ? O3 S1 C1 106.34(6) . . ? O5 S1 C1 106.41(6) . . ? O4 S1 C1 104.95(6) . . ? O3 S1 Cu1 27.58(4) . . ? O5 S1 Cu1 107.95(4) . . ? O4 S1 Cu1 93.50(4) . . ? C1 S1 Cu1 131.22(4) . . ? S1 O3 Cu1 136.58(6) . . ? C3 C1 C2 118.18(11) . . ? C3 C1 S1 123.02(9) . . ? C2 C1 S1 118.74(9) . . ? C2 C2 C1 120.60(7) 8_565 . ? C2 C2 Cl1 118.34(4) 8_565 . ? C1 C2 Cl1 120.95(9) . . ? C1 C3 C3 120.47(7) . 8_565 ? C1 C3 Cl2 122.23(10) . . ? C3 C3 Cl2 117.17(4) 8_565 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 S1 O3 32.61(10) 5_567 . . . ? O1 Cu1 S1 O3 -147.39(10) . . . . ? O2 Cu1 S1 O3 119.19(10) . . . . ? O2 Cu1 S1 O3 -60.81(10) 5_567 . . . ? O3 Cu1 S1 O3 180.0 5_567 . . . ? O1 Cu1 S1 O5 -70.51(5) 5_567 . . . ? O1 Cu1 S1 O5 109.49(5) . . . . ? O2 Cu1 S1 O5 16.07(5) . . . . ? O2 Cu1 S1 O5 -163.93(5) 5_567 . . . ? O3 Cu1 S1 O5 -103.12(10) . . . . ? O3 Cu1 S1 O5 76.88(10) 5_567 . . . ? O1 Cu1 S1 O4 175.63(5) 5_567 . . . ? O1 Cu1 S1 O4 -4.37(5) . . . . ? O2 Cu1 S1 O4 -97.80(5) . . . . ? O2 Cu1 S1 O4 82.20(5) 5_567 . . . ? O3 Cu1 S1 O4 143.01(10) . . . . ? O3 Cu1 S1 O4 -36.99(10) 5_567 . . . ? O1 Cu1 S1 C1 62.22(6) 5_567 . . . ? O1 Cu1 S1 C1 -117.78(6) . . . . ? O2 Cu1 S1 C1 148.79(6) . . . . ? O2 Cu1 S1 C1 -31.21(6) 5_567 . . . ? O3 Cu1 S1 C1 29.60(10) . . . . ? O3 Cu1 S1 C1 -150.40(10) 5_567 . . . ? O5 S1 O3 Cu1 86.99(10) . . . . ? O4 S1 O3 Cu1 -41.51(11) . . . . ? C1 S1 O3 Cu1 -157.22(8) . . . . ? O1 Cu1 O3 S1 -148.56(9) 5_567 . . . ? O1 Cu1 O3 S1 31.44(9) . . . . ? O2 Cu1 O3 S1 -60.22(10) . . . . ? O2 Cu1 O3 S1 119.78(10) 5_567 . . . ? O3 Cu1 O3 S1 58(7) 5_567 . . . ? O3 S1 C1 C3 -141.08(11) . . . . ? O5 S1 C1 C3 -21.63(13) . . . . ? O4 S1 C1 C3 96.59(12) . . . . ? Cu1 S1 C1 C3 -154.87(9) . . . . ? O3 S1 C1 C2 41.84(12) . . . . ? O5 S1 C1 C2 161.29(10) . . . . ? O4 S1 C1 C2 -80.49(11) . . . . ? Cu1 S1 C1 C2 28.05(12) . . . . ? C3 C1 C2 C2 9.87(14) . . . 8_565 ? S1 C1 C2 C2 -172.90(4) . . . 8_565 ? C3 C1 C2 Cl1 -166.06(10) . . . . ? S1 C1 C2 Cl1 11.16(15) . . . . ? C2 C1 C3 C3 -9.86(14) . . . 8_565 ? S1 C1 C3 C3 173.04(5) . . . 8_565 ? C2 C1 C3 Cl2 165.80(10) . . . . ? S1 C1 C3 Cl2 -11.30(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 35.07 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.004 _refine_diff_density_min -1.370 _refine_diff_density_rms 0.095 data_d:\struktur\naclpbds\naclpbds _database_code_depnum_ccdc_archive 'CCDC 776935' #TrackingRef '1155_web_deposit_cif_file_0_ChristinaZitzer_1273684230.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H2 Cl2 Na O4 S' _chemical_formula_weight 228.00 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.5673(16) _cell_length_b 5.5847(5) _cell_length_c 10.7230(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.488(17) _cell_angle_gamma 90.00 _cell_volume 692.47(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4186 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 1.253 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5456 _exptl_absorpt_correction_T_max 0.8956 _exptl_absorpt_process_details 'Stoe X-RED 1.22, 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method '\f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9049 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1588 _reflns_number_gt 1389 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'STOE X-RED 1.22, 2001' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.0000P] 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 1588 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0523 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Na1 Na 0.37564(5) -0.53277(11) 0.30126(5) 0.01386(13) Uani 1 1 d . . . O4 O 0.56625(8) -0.3955(2) 0.30895(10) 0.0172(2) Uani 1 1 d . . . H1 H 0.6012 -0.5052 0.2751 0.026 Uiso 1 1 d R . . H2 H 0.6011 -0.3695 0.3779 0.026 Uiso 1 1 d R . . S1 S 0.28104(3) -1.01796(6) 0.48481(3) 0.00911(9) Uani 1 1 d . . . O1 O 0.31613(8) -0.7712(2) 0.46359(9) 0.0130(2) Uani 1 1 d . . . O2 O 0.31312(8) -1.1713(2) 0.38249(9) 0.0156(2) Uani 1 1 d . . . O3 O 0.31540(8) -1.1084(2) 0.60693(9) 0.0145(2) Uani 1 1 d . . . C1 C 0.12326(10) -1.0110(3) 0.48934(11) 0.0087(3) Uani 1 1 d . . . C2 C 0.07051(10) -0.8395(3) 0.56386(12) 0.0093(2) Uani 1 1 d . . . Cl1 Cl 0.15179(2) -0.63705(6) 0.65101(3) 0.01256(9) Uani 1 1 d . . . C3 C -0.05069(10) -0.8255(3) 0.57371(11) 0.0092(2) Uani 1 1 d . . . Cl2 Cl -0.10254(3) -0.59733(6) 0.66436(3) 0.01450(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 Na1 0.0146(3) 0.0142(4) 0.0128(3) 0.0007(2) 0.00137(19) -0.0008(2) O4 0.0138(5) 0.0161(7) 0.0219(5) -0.0045(4) 0.0002(4) -0.0006(4) S1 0.00783(14) 0.0101(2) 0.00942(16) -0.00090(11) 0.00104(10) -0.00029(11) O1 0.0130(4) 0.0125(6) 0.0137(5) 0.0007(4) 0.0027(3) -0.0027(4) O2 0.0123(4) 0.0174(6) 0.0173(5) -0.0066(4) 0.0049(3) -0.0001(4) O3 0.0129(4) 0.0168(6) 0.0137(5) 0.0027(4) -0.0026(3) 0.0001(4) C1 0.0088(6) 0.0096(8) 0.0078(5) 0.0012(4) 0.0010(4) 0.0000(4) C2 0.0110(5) 0.0082(7) 0.0087(5) 0.0003(5) -0.0003(4) -0.0015(4) Cl1 0.01094(15) 0.0133(2) 0.01341(16) -0.00613(11) 0.00054(10) -0.00301(11) C3 0.0109(5) 0.0094(7) 0.0073(5) -0.0006(5) 0.0014(4) 0.0008(5) Cl2 0.01152(15) 0.0139(2) 0.01811(18) -0.00889(12) 0.00151(11) 0.00078(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O1 2.3108(11) . ? Na1 O3 2.3182(12) 4_545 ? Na1 O2 2.3215(12) 1_565 ? Na1 O4 2.3337(11) . ? Na1 O4 2.4482(13) 2_645 ? Na1 Cl2 3.2717(8) 3_546 ? Na1 H1 2.6357 . ? O4 Na1 2.4482(13) 2_655 ? O4 H1 0.8231 . ? O4 H2 0.8455 . ? S1 O2 1.4477(11) . ? S1 O3 1.4494(10) . ? S1 O1 1.4559(12) . ? S1 C1 1.8275(13) . ? O2 Na1 2.3215(12) 1_545 ? O3 Na1 2.3182(12) 4_546 ? C1 C2 1.3973(18) . ? C1 C3 1.4023(18) 3_536 ? C2 C3 1.4108(17) . ? C2 Cl1 1.7293(14) . ? C3 C1 1.4023(18) 3_536 ? C3 Cl2 1.7201(14) . ? Cl2 Na1 3.2717(8) 3_546 ? 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 Na1 O3 141.69(4) . 4_545 ? O1 Na1 O2 96.70(4) . 1_565 ? O3 Na1 O2 87.26(4) 4_545 1_565 ? O1 Na1 O4 117.54(4) . . ? O3 Na1 O4 100.47(5) 4_545 . ? O2 Na1 O4 90.25(4) 1_565 . ? O1 Na1 O4 88.71(4) . 2_645 ? O3 Na1 O4 85.84(4) 4_545 2_645 ? O2 Na1 O4 173.10(5) 1_565 2_645 ? O4 Na1 O4 91.02(3) . 2_645 ? O1 Na1 Cl2 74.68(3) . 3_546 ? O3 Na1 Cl2 75.95(3) 4_545 3_546 ? O2 Na1 Cl2 56.87(3) 1_565 3_546 ? O4 Na1 Cl2 146.85(4) . 3_546 ? O4 Na1 Cl2 121.07(3) 2_645 3_546 ? O1 Na1 Na1 143.54(4) . 2_655 ? O3 Na1 Na1 74.28(3) 4_545 2_655 ? O2 Na1 Na1 74.98(3) 1_565 2_655 ? O4 Na1 Na1 29.91(3) . 2_655 ? O4 Na1 Na1 103.10(3) 2_645 2_655 ? Cl2 Na1 Na1 123.701(17) 3_546 2_655 ? O1 Na1 Na1 91.93(3) . 2_645 ? O3 Na1 Na1 100.59(4) 4_545 2_645 ? O2 Na1 Na1 154.62(3) 1_565 2_645 ? O4 Na1 Na1 64.68(3) . 2_645 ? O4 Na1 Na1 28.38(2) 2_645 2_645 ? Cl2 Na1 Na1 148.407(19) 3_546 2_645 ? Na1 Na1 Na1 83.91(2) 2_655 2_645 ? O1 Na1 H1 115.4 . . ? O3 Na1 H1 99.2 4_545 . ? O2 Na1 H1 107.9 1_565 . ? O4 Na1 H1 17.8 . . ? O4 Na1 H1 73.3 2_645 . ? Cl2 Na1 H1 163.8 3_546 . ? Na1 Na1 H1 40.8 2_655 . ? Na1 Na1 H1 47.2 2_645 . ? Na1 O4 Na1 121.71(5) . 2_655 ? Na1 O4 H1 102.4 . . ? Na1 O4 H1 105.0 2_655 . ? Na1 O4 H2 121.0 . . ? Na1 O4 H2 98.6 2_655 . ? H1 O4 H2 106.6 . . ? O2 S1 O3 114.13(7) . . ? O2 S1 O1 111.31(6) . . ? O3 S1 O1 113.58(6) . . ? O2 S1 C1 107.98(6) . . ? O3 S1 C1 103.54(6) . . ? O1 S1 C1 105.46(6) . . ? S1 O1 Na1 138.84(6) . . ? S1 O2 Na1 152.52(7) . 1_545 ? S1 O3 Na1 139.69(7) . 4_546 ? C2 C1 C3 117.20(11) . 3_536 ? C2 C1 S1 118.76(10) . . ? C3 C1 S1 123.99(10) 3_536 . ? C1 C2 C3 122.03(12) . . ? C1 C2 Cl1 121.18(9) . . ? C3 C2 Cl1 116.78(10) . . ? C1 C3 C2 120.75(12) 3_536 . ? C1 C3 Cl2 122.81(10) 3_536 . ? C2 C3 Cl2 116.44(10) . . ? C3 Cl2 Na1 125.46(5) . 3_546 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Na1 O4 Na1 -155.87(5) . . . 2_655 ? O3 Na1 O4 Na1 29.09(7) 4_545 . . 2_655 ? O2 Na1 O4 Na1 -58.17(5) 1_565 . . 2_655 ? O4 Na1 O4 Na1 115.05(8) 2_645 . . 2_655 ? Cl2 Na1 O4 Na1 -51.20(9) 3_546 . . 2_655 ? Na1 Na1 O4 Na1 125.95(6) 2_645 . . 2_655 ? O2 S1 O1 Na1 15.55(10) . . . . ? O3 S1 O1 Na1 146.02(8) . . . . ? C1 S1 O1 Na1 -101.30(9) . . . . ? O3 Na1 O1 S1 59.53(12) 4_545 . . . ? O2 Na1 O1 S1 153.61(8) 1_565 . . . ? O4 Na1 O1 S1 -112.59(9) . . . . ? O4 Na1 O1 S1 -22.11(9) 2_645 . . . ? Cl2 Na1 O1 S1 100.68(9) 3_546 . . . ? Na1 Na1 O1 S1 -132.65(7) 2_655 . . . ? Na1 Na1 O1 S1 -50.31(9) 2_645 . . . ? O3 S1 O2 Na1 14.57(15) . . . 1_545 ? O1 S1 O2 Na1 144.75(12) . . . 1_545 ? C1 S1 O2 Na1 -99.95(13) . . . 1_545 ? O2 S1 O3 Na1 146.73(8) . . . 4_546 ? O1 S1 O3 Na1 17.69(11) . . . 4_546 ? C1 S1 O3 Na1 -96.15(10) . . . 4_546 ? O2 S1 C1 C2 -167.62(10) . . . . ? O3 S1 C1 C2 71.04(12) . . . . ? O1 S1 C1 C2 -48.53(12) . . . . ? O2 S1 C1 C3 15.18(13) . . . 3_536 ? O3 S1 C1 C3 -106.16(12) . . . 3_536 ? O1 S1 C1 C3 134.27(12) . . . 3_536 ? C3 C1 C2 C3 -1.6(2) 3_536 . . . ? S1 C1 C2 C3 -178.97(10) . . . . ? C3 C1 C2 Cl1 177.24(10) 3_536 . . . ? S1 C1 C2 Cl1 -0.15(16) . . . . ? C1 C2 C3 C1 1.6(2) . . . 3_536 ? Cl1 C2 C3 C1 -177.23(10) . . . 3_536 ? C1 C2 C3 Cl2 -177.54(10) . . . . ? Cl1 C2 C3 Cl2 3.59(14) . . . . ? C1 C3 Cl2 Na1 -3.98(14) 3_536 . . 3_546 ? C2 C3 Cl2 Na1 175.18(8) . . . 3_546 ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.418 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.067 data_c:\tm216\tm216 _database_code_depnum_ccdc_archive 'CCDC 777578' #TrackingRef '1206_web_deposit_cif_file_0_ChristinaZitzer_1274194827.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 Cu F4 O12 S2' _chemical_formula_weight 479.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1045(2) _cell_length_b 7.4468(3) _cell_length_c 10.7777(4) _cell_angle_alpha 85.627(2) _cell_angle_beta 77.449(2) _cell_angle_gamma 76.015(2) _cell_volume 387.92(3) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9669 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 40.11 _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 241 _exptl_absorpt_coefficient_mu 1.783 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4313 _exptl_absorpt_correction_T_max 0.9067 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\F and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20526 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 40.30 _reflns_number_total 4896 _reflns_number_gt 4069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0424P)^2^+0.0253P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4896 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.0000 0.01359(4) Uani 1 2 d S . . S2 S 0.80720(4) 0.97144(3) -0.26730(2) 0.01355(4) Uani 1 1 d . . . O1 O 0.57820(15) 1.00403(10) -0.15676(7) 0.01809(12) Uani 1 1 d . . . O2 O 0.30361(15) 0.34305(10) -0.06204(8) 0.01908(13) Uani 1 1 d . . . H3 H 0.186(4) 0.377(3) -0.100(2) 0.037(5) Uiso 1 1 d . . . H5 H 0.388(4) 0.249(3) -0.0927(19) 0.033(5) Uiso 1 1 d . . . O3 O 0.98346(15) 0.78629(10) -0.26568(8) 0.01958(13) Uani 1 1 d . . . O4 O 0.95745(16) 1.11575(11) -0.29014(8) 0.02035(13) Uani 1 1 d . . . O5 O 0.30451(16) 0.72803(10) -0.07812(8) 0.02044(13) Uani 1 1 d . . . H4 H 0.381(4) 0.806(3) -0.0994(19) 0.035(5) Uiso 1 1 d . . . H6 H 0.213(5) 0.729(3) -0.124(2) 0.046(6) Uiso 1 1 d . . . C1 C 0.64283(17) 0.98300(11) -0.39899(8) 0.01342(12) Uani 1 1 d . . . F1 F 0.5086(2) 1.30841(10) -0.38630(10) 0.0452(3) Uani 1 1 d . . . F2 F 0.7405(3) 0.65717(10) -0.42266(11) 0.0519(3) Uani 1 1 d . . . C2 C 0.5143(2) 1.15412(13) -0.44332(10) 0.02008(17) Uani 1 1 d . . . C3 C 0.6239(2) 0.82837(13) -0.45763(10) 0.02086(17) Uani 1 1 d . . . O6 O 0.12405(16) 0.55375(11) 0.17786(8) 0.01874(12) Uani 1 1 d . . . H1 H 0.110(4) 0.634(3) 0.2167(18) 0.028(4) Uiso 1 1 d . . . H2 H 0.110(4) 0.480(3) 0.227(2) 0.035(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01321(6) 0.01275(7) 0.01704(7) 0.00103(5) -0.00793(5) -0.00338(4) S2 0.01508(8) 0.01383(8) 0.01349(8) 0.00053(6) -0.00610(7) -0.00415(6) O1 0.0215(3) 0.0194(3) 0.0137(3) -0.0002(2) -0.0029(2) -0.0061(2) O2 0.0179(3) 0.0162(3) 0.0260(3) -0.0033(2) -0.0114(3) -0.0025(2) O3 0.0206(3) 0.0160(3) 0.0236(3) -0.0001(2) -0.0119(3) -0.0004(2) O4 0.0212(3) 0.0208(3) 0.0233(3) -0.0001(3) -0.0074(3) -0.0107(2) O5 0.0206(3) 0.0174(3) 0.0280(4) 0.0064(3) -0.0145(3) -0.0069(2) C1 0.0154(3) 0.0132(3) 0.0130(3) 0.0005(2) -0.0054(2) -0.0039(2) F1 0.0783(7) 0.0139(3) 0.0566(6) -0.0082(3) -0.0528(5) 0.0011(3) F2 0.0951(8) 0.0120(3) 0.0666(6) 0.0024(3) -0.0676(6) -0.0024(4) C2 0.0305(4) 0.0117(3) 0.0224(4) -0.0011(3) -0.0155(4) -0.0039(3) C3 0.0321(5) 0.0116(3) 0.0232(4) 0.0015(3) -0.0176(4) -0.0032(3) O6 0.0216(3) 0.0164(3) 0.0202(3) 0.0002(2) -0.0083(2) -0.0047(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 Cu1 O2 1.9481(7) 2_665 ? Cu1 O2 1.9481(7) . ? Cu1 O5 1.9790(7) . ? Cu1 O5 1.9790(7) 2_665 ? Cu1 O6 2.3800(8) 2_665 ? Cu1 O6 2.3800(8) . ? S2 O4 1.4421(7) . ? S2 O3 1.4541(7) . ? S2 O1 1.4650(8) . ? S2 C1 1.7860(8) . ? O2 H3 0.78(2) . ? O2 H5 0.78(2) . ? O5 H4 0.769(19) . ? O5 H6 0.75(2) . ? C1 C2 1.3864(12) . ? C1 C3 1.3878(13) . ? F1 C2 1.3350(12) . ? F2 C3 1.3339(12) . ? C2 C3 1.3839(13) 2_674 ? C3 C2 1.3839(13) 2_674 ? O6 H1 0.73(2) . ? O6 H2 0.74(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.00(4) 2_665 . ? O2 Cu1 O5 86.52(3) 2_665 . ? O2 Cu1 O5 93.48(3) . . ? O2 Cu1 O5 93.48(3) 2_665 2_665 ? O2 Cu1 O5 86.52(3) . 2_665 ? O5 Cu1 O5 180.00(5) . 2_665 ? O2 Cu1 O6 86.42(3) 2_665 2_665 ? O2 Cu1 O6 93.58(3) . 2_665 ? O5 Cu1 O6 93.10(3) . 2_665 ? O5 Cu1 O6 86.90(3) 2_665 2_665 ? O2 Cu1 O6 93.58(3) 2_665 . ? O2 Cu1 O6 86.42(3) . . ? O5 Cu1 O6 86.90(3) . . ? O5 Cu1 O6 93.10(3) 2_665 . ? O6 Cu1 O6 180.0 2_665 . ? O4 S2 O3 113.49(5) . . ? O4 S2 O1 113.23(5) . . ? O3 S2 O1 112.63(5) . . ? O4 S2 C1 106.07(4) . . ? O3 S2 C1 106.36(4) . . ? O1 S2 C1 104.11(4) . . ? Cu1 O2 H3 125.7(15) . . ? Cu1 O2 H5 118.7(14) . . ? H3 O2 H5 104(2) . . ? Cu1 O5 H4 118.0(15) . . ? Cu1 O5 H6 124.0(16) . . ? H4 O5 H6 107(2) . . ? C2 C1 C3 116.83(8) . . ? C2 C1 S2 119.38(7) . . ? C3 C1 S2 123.72(7) . . ? F1 C2 C3 117.64(8) . 2_674 ? F1 C2 C1 120.23(8) . . ? C3 C2 C1 122.04(8) 2_674 . ? F2 C3 C2 117.09(9) . 2_674 ? F2 C3 C1 121.78(8) . . ? C2 C3 C1 121.12(8) 2_674 . ? Cu1 O6 H1 116.9(14) . . ? Cu1 O6 H2 119.2(16) . . ? H1 O6 H2 102(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 O4 S2 C1 C2 -43.54(9) . . . . ? O3 S2 C1 C2 -164.66(8) . . . . ? O1 S2 C1 C2 76.18(9) . . . . ? O4 S2 C1 C3 139.56(9) . . . . ? O3 S2 C1 C3 18.44(10) . . . . ? O1 S2 C1 C3 -100.73(9) . . . . ? C3 C1 C2 F1 175.71(11) . . . . ? S2 C1 C2 F1 -1.40(15) . . . . ? C3 C1 C2 C3 -0.83(18) . . . 2_674 ? S2 C1 C2 C3 -177.94(9) . . . 2_674 ? C2 C1 C3 F2 179.83(11) . . . . ? S2 C1 C3 F2 -3.19(16) . . . . ? C2 C1 C3 C2 0.82(18) . . . 2_674 ? S2 C1 C3 C2 177.80(9) . . . 2_674 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 40.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.166 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.084