Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Andrew S.Weller' _publ_contact_author_address ; Department of Chemistry University of Bath Bath, BA2 7AY United Kingdom ; _publ_contact_author_email a.s.weller@bath.ac.uk _publ_contact_author_phone '44 1225 38 3394' _publ_contact_author_fax '44 1225 82 6231' loop_ _publ_author_name _publ_author_address 'Jamie H. Cotgreave' ;University of Bath Department of Chemistry Bath, BA2 7AY United Kingdom ; 'David Colclough' ;GloxoSmithKline Old Powder Mills, Leigh, Nr Tonbridge, Kent, TN11 9AN, United Kingdom ; 'Gabriele Kociok-Kohn' ;University of Bath Department of Chemistry Bath, BA2 7AY United Kingdom ; 'Guiseppe Ruggiero' ;University of Bath Department of Chemistry Bath, BA2 7AY United Kingdom ; 'Christopher G. Frost' ;University of Bath Department of Chemistry Bath, BA2 7AY United Kingdom ; ; A.S.Weller ; ;University of Bath Department of Chemistry Bath, BA2 7AY United Kingdom ; _publ_section_title ; Well-defined indium(III) N-heterocyclic carbene complexes with triflate ligands: Structural models for the In(OTf)3 catalyst ; data_k03asw25 _database_code_depnum_ccdc_archive 'CCDC 234195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 1' _chemical_melting_point ? _chemical_formula_moiety 'C23 H30 Cl In N2' _chemical_formula_sum 'C23 H30 Cl In N2' _chemical_formula_weight 484.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' In In -0.7276 1.3100 '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 8.28900(10) _cell_length_b 11.08700(10) _cell_length_c 13.6710(2) _cell_angle_alpha 68.7250(10) _cell_angle_beta 86.5340(10) _cell_angle_gamma 75.1380(10) _cell_volume 1130.84(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.173 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16860 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 27.66 _reflns_number_total 5183 _reflns_number_gt 4708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Nonius program suite version 1.9 (1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119. ; _computing_structure_refinement ; SHELX97-2 Program for Crystal Structure Analysis. G. M. Sheldrick, Institut f. Anorg. Chemie der Universitat, Tammanstrasse 4, D-3400 Gottingen, Germany, 1998. ; _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565 ; _computing_publication_material 'SHELX97-2, G. M. Sheldrick' _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^)+(0.0252P)^2^+0.5693P] 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 SHELXL _refine_ls_extinction_coef 0.0060(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5183 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 In1 In 0.200448(17) 0.080539(15) -0.218587(11) 0.02148(7) Uani 1 1 d . . . Cl1 Cl 0.11556(7) 0.09745(6) -0.39496(4) 0.02946(13) Uani 1 1 d . . . C11 C 0.5988(3) -0.2002(2) -0.26991(16) 0.0231(4) Uani 1 1 d . . . N2 N 0.4778(2) 0.24170(18) -0.33385(14) 0.0219(4) Uani 1 1 d . . . C20 C 0.2682(3) 0.4527(2) -0.42199(16) 0.0219(4) Uani 1 1 d . . . N1 N 0.5888(2) 0.03141(18) -0.28804(14) 0.0221(4) Uani 1 1 d . . . C19 C 0.1661(3) 0.5716(2) -0.41792(17) 0.0234(4) Uani 1 1 d . . . H19 H 0.0919 0.6291 -0.4758 0.028 Uiso 1 1 calc R . . C3 C 0.6325(3) 0.2271(2) -0.37945(19) 0.0301(5) Uani 1 1 d . . . H3 H 0.6801 0.2971 -0.4225 0.036 Uiso 1 1 calc R . . C7 C 0.7091(3) -0.1538(2) -0.12890(18) 0.0263(5) Uani 1 1 d . . . C17 C 0.2801(3) 0.5238(2) -0.24743(18) 0.0274(5) Uani 1 1 d . . . H17 H 0.2859 0.5494 -0.1888 0.033 Uiso 1 1 calc R . . C2 C 0.7018(3) 0.0954(3) -0.3511(2) 0.0319(5) Uani 1 1 d . . . H2 H 0.8075 0.0541 -0.3705 0.038 Uiso 1 1 calc R . . C8 C 0.7547(3) -0.2901(2) -0.07201(18) 0.0281(5) Uani 1 1 d . . . H8 H 0.8089 -0.3211 -0.0049 0.034 Uiso 1 1 calc R . . C23 C 0.2670(3) 0.4173(2) -0.51900(18) 0.0295(5) Uani 1 1 d . . . H23A H 0.3721 0.4238 -0.5550 0.044 Uiso 1 1 calc R . . H23B H 0.1732 0.4795 -0.5663 0.044 Uiso 1 1 calc R . . H23C H 0.2550 0.3258 -0.4984 0.044 Uiso 1 1 calc R . . C6 C 0.6305(3) -0.1113(2) -0.22751(17) 0.0223(4) Uani 1 1 d . . . C16 C 0.3819(3) 0.4030(2) -0.24674(17) 0.0251(5) Uani 1 1 d . . . C22 C 0.0585(3) 0.7390(3) -0.3285(2) 0.0355(6) Uani 1 1 d . . . H22A H 0.0178 0.7258 -0.2575 0.053 Uiso 1 1 calc R . . H22B H -0.0366 0.7686 -0.3781 0.053 Uiso 1 1 calc R . . H22C H 0.1222 0.8071 -0.3483 0.053 Uiso 1 1 calc R . . C18 C 0.1697(3) 0.6089(2) -0.33090(18) 0.0259(5) Uani 1 1 d . . . C15 C 0.3723(3) 0.3683(2) -0.33496(17) 0.0215(4) Uani 1 1 d . . . C9 C 0.7235(3) -0.3831(2) -0.11002(18) 0.0270(5) Uani 1 1 d . . . C12 C 0.7418(3) -0.0564(3) -0.0841(2) 0.0375(6) Uani 1 1 d . . . H12A H 0.6369 -0.0117 -0.0610 0.056 Uiso 1 1 calc R . . H12B H 0.7885 0.0106 -0.1380 0.056 Uiso 1 1 calc R . . H12C H 0.8214 -0.1045 -0.0240 0.056 Uiso 1 1 calc R . . C21 C 0.4987(3) 0.3125(3) -0.1547(2) 0.0358(6) Uani 1 1 d . . . H21A H 0.4994 0.3585 -0.1056 0.054 Uiso 1 1 calc R . . H21B H 0.6117 0.2890 -0.1795 0.054 Uiso 1 1 calc R . . H21C H 0.4611 0.2308 -0.1189 0.054 Uiso 1 1 calc R . . C10 C 0.6461(3) -0.3356(2) -0.20895(18) 0.0265(5) Uani 1 1 d . . . H10 H 0.6247 -0.3980 -0.2359 0.032 Uiso 1 1 calc R . . C14 C 0.5192(3) -0.1521(3) -0.37809(18) 0.0330(5) Uani 1 1 d . . . H14A H 0.6029 -0.1304 -0.4310 0.050 Uiso 1 1 calc R . . H14B H 0.4277 -0.0721 -0.3881 0.050 Uiso 1 1 calc R . . H14C H 0.4754 -0.2225 -0.3856 0.050 Uiso 1 1 calc R . . C13 C 0.7719(4) -0.5303(3) -0.0452(2) 0.0371(6) Uani 1 1 d . . . H13A H 0.8636 -0.5489 0.0044 0.056 Uiso 1 1 calc R . . H13B H 0.8081 -0.5813 -0.0916 0.056 Uiso 1 1 calc R . . H13C H 0.6756 -0.5566 -0.0063 0.056 Uiso 1 1 calc R . . C5 C 0.2322(3) -0.1239(2) -0.1133(2) 0.0342(5) Uani 1 1 d . . . H5A H 0.2177 -0.1266 -0.0409 0.051 Uiso 1 1 calc R . . H5B H 0.3445 -0.1763 -0.1196 0.051 Uiso 1 1 calc R . . H5C H 0.1489 -0.1617 -0.1316 0.051 Uiso 1 1 calc R . . C4 C 0.0277(3) 0.2510(3) -0.1963(2) 0.0326(5) Uani 1 1 d . . . H4A H -0.0496 0.2197 -0.1414 0.049 Uiso 1 1 calc R . . H4B H -0.0356 0.3081 -0.2621 0.049 Uiso 1 1 calc R . . H4C H 0.0901 0.3022 -0.1752 0.049 Uiso 1 1 calc R . . C1 C 0.4502(3) 0.1209(2) -0.27699(16) 0.0196(4) 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 In1 0.01736(10) 0.01933(10) 0.02453(10) -0.00479(6) 0.00419(6) -0.00453(6) Cl1 0.0249(3) 0.0330(3) 0.0300(3) -0.0096(2) -0.0012(2) -0.0083(2) C11 0.0196(10) 0.0240(11) 0.0233(10) -0.0089(9) 0.0043(8) -0.0015(9) N2 0.0185(9) 0.0183(9) 0.0263(9) -0.0057(7) 0.0041(7) -0.0044(7) C20 0.0225(10) 0.0185(11) 0.0234(10) -0.0047(8) 0.0045(8) -0.0084(9) N1 0.0165(8) 0.0191(9) 0.0279(9) -0.0068(7) 0.0042(7) -0.0028(7) C19 0.0214(10) 0.0193(11) 0.0253(10) -0.0027(9) 0.0022(8) -0.0060(9) C3 0.0225(11) 0.0270(13) 0.0375(13) -0.0070(10) 0.0136(10) -0.0100(10) C7 0.0206(10) 0.0245(12) 0.0323(11) -0.0112(10) -0.0003(9) -0.0016(9) C17 0.0316(12) 0.0245(12) 0.0280(11) -0.0109(9) 0.0045(9) -0.0092(10) C2 0.0222(11) 0.0288(13) 0.0410(13) -0.0100(11) 0.0132(10) -0.0068(10) C8 0.0258(11) 0.0245(12) 0.0293(11) -0.0082(10) -0.0032(9) 0.0005(9) C23 0.0356(13) 0.0261(12) 0.0256(11) -0.0083(9) 0.0018(10) -0.0075(10) C6 0.0169(10) 0.0189(11) 0.0271(10) -0.0060(9) 0.0036(8) -0.0016(8) C16 0.0237(11) 0.0243(12) 0.0256(11) -0.0057(9) 0.0015(9) -0.0084(9) C22 0.0366(14) 0.0262(13) 0.0410(14) -0.0140(11) 0.0047(11) -0.0014(11) C18 0.0250(11) 0.0198(11) 0.0313(11) -0.0072(9) 0.0064(9) -0.0070(9) C15 0.0193(10) 0.0161(10) 0.0277(10) -0.0054(8) 0.0047(8) -0.0064(8) C9 0.0251(11) 0.0207(11) 0.0303(11) -0.0073(9) 0.0029(9) -0.0005(9) C12 0.0373(14) 0.0283(14) 0.0475(15) -0.0155(12) -0.0131(12) -0.0031(11) C21 0.0371(14) 0.0328(14) 0.0339(13) -0.0117(11) -0.0072(11) -0.0016(11) C10 0.0283(11) 0.0232(12) 0.0289(11) -0.0115(9) 0.0037(9) -0.0052(9) C14 0.0395(14) 0.0292(13) 0.0270(11) -0.0115(10) -0.0026(10) 0.0000(11) C13 0.0470(15) 0.0217(12) 0.0357(13) -0.0073(10) -0.0048(11) -0.0003(11) C5 0.0349(13) 0.0251(13) 0.0346(13) -0.0009(10) 0.0057(10) -0.0096(11) C4 0.0267(12) 0.0297(13) 0.0385(13) -0.0138(11) 0.0078(10) -0.0017(10) C1 0.0166(9) 0.0171(10) 0.0230(10) -0.0056(8) 0.0011(8) -0.0030(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 In1 C5 2.156(2) . ? In1 C4 2.166(2) . ? In1 C1 2.267(2) . ? In1 Cl1 2.4807(6) . ? C11 C10 1.390(3) . ? C11 C6 1.394(3) . ? C11 C14 1.507(3) . ? N2 C1 1.353(3) . ? N2 C3 1.389(3) . ? N2 C15 1.447(3) . ? C20 C19 1.390(3) . ? C20 C15 1.392(3) . ? C20 C23 1.515(3) . ? N1 C1 1.352(3) . ? N1 C2 1.387(3) . ? N1 C6 1.453(3) . ? C19 C18 1.398(3) . ? C3 C2 1.341(3) . ? C7 C8 1.386(3) . ? C7 C6 1.397(3) . ? C7 C12 1.505(3) . ? C17 C16 1.385(3) . ? C17 C18 1.390(3) . ? C8 C9 1.394(3) . ? C16 C15 1.404(3) . ? C16 C21 1.503(3) . ? C22 C18 1.510(3) . ? C9 C10 1.390(3) . ? C9 C13 1.505(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 C5 In1 C4 124.47(10) . . ? C5 In1 C1 110.77(9) . . ? C4 In1 C1 112.95(9) . . ? C5 In1 Cl1 108.28(7) . . ? C4 In1 Cl1 103.13(7) . . ? C1 In1 Cl1 91.45(5) . . ? C10 C11 C6 117.2(2) . . ? C10 C11 C14 121.2(2) . . ? C6 C11 C14 121.5(2) . . ? C1 N2 C3 110.75(18) . . ? C1 N2 C15 124.61(17) . . ? C3 N2 C15 124.09(18) . . ? C19 C20 C15 118.06(19) . . ? C19 C20 C23 120.7(2) . . ? C15 C20 C23 121.2(2) . . ? C1 N1 C2 111.10(19) . . ? C1 N1 C6 125.13(18) . . ? C2 N1 C6 122.84(18) . . ? C20 C19 C18 121.7(2) . . ? C2 C3 N2 107.0(2) . . ? C8 C7 C6 117.6(2) . . ? C8 C7 C12 120.5(2) . . ? C6 C7 C12 121.9(2) . . ? C16 C17 C18 122.3(2) . . ? C3 C2 N1 106.6(2) . . ? C7 C8 C9 122.1(2) . . ? C11 C6 C7 122.6(2) . . ? C11 C6 N1 120.23(19) . . ? C7 C6 N1 117.14(19) . . ? C17 C16 C15 117.7(2) . . ? C17 C16 C21 121.0(2) . . ? C15 C16 C21 121.3(2) . . ? C17 C18 C19 118.1(2) . . ? C17 C18 C22 121.0(2) . . ? C19 C18 C22 120.9(2) . . ? C20 C15 C16 122.0(2) . . ? C20 C15 N2 120.38(19) . . ? C16 C15 N2 117.61(19) . . ? C10 C9 C8 117.9(2) . . ? C10 C9 C13 121.4(2) . . ? C8 C9 C13 120.7(2) . . ? C11 C10 C9 122.5(2) . . ? N1 C1 N2 104.64(17) . . ? N1 C1 In1 127.06(15) . . ? N2 C1 In1 126.11(15) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.860 _refine_diff_density_min -1.101 _refine_diff_density_rms 0.139 #=== END data_k03asw34 _database_code_depnum_ccdc_archive 'CCDC 234196' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 3' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 Cl2 F6 In N2 O6 S2' _chemical_formula_weight 817.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.42300(10) _cell_length_b 12.5040(2) _cell_length_c 14.5090(2) _cell_angle_alpha 85.3780(10) _cell_angle_beta 83.6180(10) _cell_angle_gamma 83.1720(10) _cell_volume 1682.95(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(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 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.058 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 30330 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 30.09 _reflns_number_total 9809 _reflns_number_gt 8689 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0242P)^2^+0.8895P] 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 9809 _refine_ls_number_parameters 465 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.038 _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 In In 0.921212(12) 0.035887(9) 0.183436(8) 0.02278(4) Uani 1 1 d . . . S1 S 0.89908(5) -0.14557(3) -0.00158(3) 0.02630(9) Uani 1 1 d . . . S2 S 1.01518(5) 0.22577(4) 0.31629(3) 0.02753(9) Uani 1 1 d . . . N1 N 0.61999(15) -0.00510(12) 0.28356(10) 0.0277(3) Uani 1 1 d . . . N2 N 0.59019(15) 0.14521(12) 0.20168(10) 0.0270(3) Uani 1 1 d . . . O1 O 0.85628(14) -0.09478(10) 0.08480(9) 0.0314(3) Uani 1 1 d . . . O2 O 0.79158(14) -0.14087(12) -0.06382(10) 0.0389(3) Uani 1 1 d . . . O3 O 1.03981(13) -0.11778(10) -0.04566(8) 0.0267(2) Uani 1 1 d . . . O4 O 0.94120(14) 0.19529(10) 0.23986(9) 0.0302(3) Uani 1 1 d . . . O5 O 0.91892(16) 0.26539(14) 0.39242(10) 0.0452(4) Uani 1 1 d . . . O6 O 1.13515(14) 0.15048(11) 0.33855(9) 0.0342(3) Uani 1 1 d . . . F1 F 0.81785(15) -0.32757(10) 0.07165(11) 0.0591(4) Uani 1 1 d . . . F2 F 0.99891(14) -0.34492(10) -0.03272(9) 0.0446(3) Uani 1 1 d . . . F3 F 1.02672(15) -0.29848(10) 0.10345(9) 0.0480(3) Uani 1 1 d . . . F4 F 0.99645(15) 0.42041(10) 0.23371(10) 0.0529(3) Uani 1 1 d . . . F5 F 1.16315(16) 0.38622(11) 0.32538(10) 0.0563(4) Uani 1 1 d . . . F6 F 1.19025(13) 0.31942(9) 0.19186(8) 0.0421(3) Uani 1 1 d . . . C1 C 1.0995(2) -0.06897(18) 0.22476(17) 0.0437(5) Uani 1 1 d . . . H1A H 1.1475 -0.1067 0.1712 0.066 Uiso 1 1 calc R . . H1B H 1.0665 -0.1219 0.2736 0.066 Uiso 1 1 calc R . . H1C H 1.1671 -0.0269 0.2486 0.066 Uiso 1 1 calc R . . C2 C 0.69030(17) 0.06334(13) 0.22342(11) 0.0229(3) Uani 1 1 d . . . C3 C 0.4764(2) 0.03327(17) 0.29924(15) 0.0401(5) Uani 1 1 d . . . H3 H 0.4048 -0.0001 0.3389 0.048 Uiso 1 1 calc R . . C4 C 0.4576(2) 0.12703(17) 0.24739(15) 0.0395(5) Uani 1 1 d . . . H4 H 0.3698 0.1722 0.2430 0.047 Uiso 1 1 calc R . . C5 C 0.6872(2) -0.10707(14) 0.32178(11) 0.0284(3) Uani 1 1 d . . . C6 C 0.6662(2) -0.20089(15) 0.28189(12) 0.0319(4) Uani 1 1 d . . . C7 C 0.7356(3) -0.29729(17) 0.31695(14) 0.0428(5) Uani 1 1 d . . . H7 H 0.7249 -0.3624 0.2903 0.051 Uiso 1 1 calc R . . C8 C 0.8202(3) -0.30118(17) 0.38995(15) 0.0483(6) Uani 1 1 d . . . C9 C 0.8358(3) -0.20630(18) 0.42844(14) 0.0459(5) Uani 1 1 d . . . H9 H 0.8935 -0.2088 0.4784 0.055 Uiso 1 1 calc R . . C10 C 0.7688(2) -0.10662(16) 0.39588(12) 0.0358(4) Uani 1 1 d . . . C11 C 0.5722(2) -0.19860(18) 0.20433(13) 0.0384(4) Uani 1 1 d . . . H11A H 0.5769 -0.2713 0.1826 0.058 Uiso 1 1 calc R . . H11B H 0.6056 -0.1491 0.1528 0.058 Uiso 1 1 calc R . . H11C H 0.4727 -0.1740 0.2270 0.058 Uiso 1 1 calc R . . C12 C 0.8941(4) -0.4078(2) 0.4267(2) 0.0778(10) Uani 1 1 d . . . H12A H 0.9942 -0.4166 0.3992 0.117 Uiso 1 1 calc R . . H12B H 0.8445 -0.4671 0.4103 0.117 Uiso 1 1 calc R . . H12C H 0.8915 -0.4088 0.4945 0.117 Uiso 1 1 calc R . . C13 C 0.7863(3) -0.00542(18) 0.44102(15) 0.0521(6) Uani 1 1 d . . . H13A H 0.8664 0.0293 0.4071 0.078 Uiso 1 1 calc R . . H13B H 0.8063 -0.0238 0.5056 0.078 Uiso 1 1 calc R . . H13C H 0.6977 0.0442 0.4398 0.078 Uiso 1 1 calc R . . C14 C 0.61537(18) 0.23572(13) 0.13559(12) 0.0263(3) Uani 1 1 d . . . C15 C 0.61958(18) 0.21880(14) 0.04137(12) 0.0267(3) Uani 1 1 d . . . C16 C 0.6462(2) 0.30605(15) -0.02182(14) 0.0331(4) Uani 1 1 d . . . H16 H 0.6496 0.2973 -0.0865 0.040 Uiso 1 1 calc R . . C17 C 0.6679(2) 0.40531(15) 0.00743(15) 0.0377(4) Uani 1 1 d . . . C18 C 0.6584(2) 0.41852(15) 0.10178(16) 0.0382(4) Uani 1 1 d . . . H18 H 0.6707 0.4870 0.1219 0.046 Uiso 1 1 calc R . . C19 C 0.6315(2) 0.33476(15) 0.16821(14) 0.0327(4) Uani 1 1 d . . . C20 C 0.5930(2) 0.11280(14) 0.00877(13) 0.0318(4) Uani 1 1 d . . . H20A H 0.4915 0.1022 0.0242 0.048 Uiso 1 1 calc R . . H20B H 0.6530 0.0542 0.0395 0.048 Uiso 1 1 calc R . . H20C H 0.6171 0.1128 -0.0587 0.048 Uiso 1 1 calc R . . C21 C 0.7035(3) 0.49635(18) -0.06299(18) 0.0496(6) Uani 1 1 d . . . H21A H 0.8068 0.5024 -0.0678 0.074 Uiso 1 1 calc R . . H21B H 0.6501 0.5642 -0.0432 0.074 Uiso 1 1 calc R . . H21C H 0.6767 0.4816 -0.1237 0.074 Uiso 1 1 calc R . . C22 C 0.6182(3) 0.35193(19) 0.27062(16) 0.0462(5) Uani 1 1 d . . . H22A H 0.6563 0.4195 0.2798 0.069 Uiso 1 1 calc R . . H22B H 0.6729 0.2916 0.3030 0.069 Uiso 1 1 calc R . . H22C H 0.5169 0.3559 0.2956 0.069 Uiso 1 1 calc R . . C23 C 0.9391(2) -0.28798(16) 0.03744(15) 0.0368(4) Uani 1 1 d . . . C24 C 1.0949(2) 0.34499(15) 0.26364(14) 0.0346(4) Uani 1 1 d . . . C25 C 1.3675(16) -0.3251(7) 0.4681(7) 0.045(3) Uiso 0.25 1 d PD A 1 H25A H 1.4578 -0.3008 0.4834 0.054 Uiso 0.25 1 calc PR A 1 H25B H 1.3048 -0.3357 0.5267 0.054 Uiso 0.25 1 calc PR A 1 Cl1 Cl 1.2808(5) -0.2253(3) 0.3934(4) 0.0604(8) Uani 0.25 1 d PD A 1 Cl2 Cl 1.4056(8) -0.4464(4) 0.4150(8) 0.143(3) Uani 0.25 1 d PD A 1 C25A C 1.3172(19) -0.3439(14) 0.4538(9) 0.093(5) Uiso 0.25 1 d PD B 2 H25C H 1.3327 -0.4072 0.4986 0.111 Uiso 0.25 1 calc PR B 2 H25D H 1.2171 -0.3109 0.4682 0.111 Uiso 0.25 1 calc PR B 2 Cl1A Cl 1.4310(12) -0.2509(10) 0.4745(7) 0.172(6) Uani 0.25 1 d PD B 2 Cl2A Cl 1.3319(12) -0.3904(6) 0.3436(7) 0.121(4) Uani 0.25 1 d PD B 2 C25B C 1.2510(11) -0.3020(11) 0.4258(8) 0.060(3) Uiso 0.25 1 d PD C 3 H25E H 1.2343 -0.3592 0.4757 0.072 Uiso 0.25 1 calc PR C 3 H25F H 1.1637 -0.2493 0.4273 0.072 Uiso 0.25 1 calc PR C 3 Cl1B Cl 1.3977(9) -0.2355(6) 0.4494(6) 0.090(3) Uani 0.25 1 d PD C 3 Cl2B Cl 1.2755(11) -0.3597(6) 0.3192(6) 0.099(3) Uani 0.25 1 d PD C 3 C25C C 1.399(3) -0.3104(10) 0.4667(16) 0.111(12) Uiso 0.25 1 d PD D 4 H25G H 1.4891 -0.2767 0.4493 0.133 Uiso 0.25 1 calc PR D 4 H25H H 1.3523 -0.2814 0.5254 0.133 Uiso 0.25 1 calc PR D 4 Cl1C Cl 1.4382(9) -0.4522(7) 0.4821(5) 0.147(3) Uani 0.25 1 d PD . 4 Cl2C Cl 1.2827(10) -0.2793(12) 0.3775(7) 0.238(9) Uani 0.25 1 d PD D 4 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 In 0.01767(6) 0.02890(6) 0.02124(6) -0.00326(4) -0.00190(4) 0.00053(4) S1 0.0226(2) 0.0315(2) 0.02572(19) -0.00857(16) 0.00177(15) -0.00613(16) S2 0.0252(2) 0.0363(2) 0.02214(18) -0.00677(16) -0.00184(15) -0.00492(17) N1 0.0233(7) 0.0340(7) 0.0234(7) 0.0061(6) 0.0000(5) -0.0002(6) N2 0.0200(7) 0.0301(7) 0.0282(7) 0.0032(6) -0.0002(5) 0.0021(5) O1 0.0342(7) 0.0331(6) 0.0274(6) -0.0099(5) 0.0069(5) -0.0099(5) O2 0.0255(7) 0.0536(9) 0.0401(7) -0.0164(6) -0.0060(6) -0.0037(6) O3 0.0222(6) 0.0351(6) 0.0230(5) -0.0027(5) -0.0002(4) -0.0060(5) O4 0.0294(6) 0.0345(6) 0.0286(6) -0.0073(5) -0.0077(5) -0.0032(5) O5 0.0370(8) 0.0690(10) 0.0304(7) -0.0181(7) 0.0051(6) -0.0068(7) O6 0.0327(7) 0.0402(7) 0.0305(6) 0.0009(5) -0.0088(5) -0.0040(6) F1 0.0512(8) 0.0399(7) 0.0848(11) -0.0110(7) 0.0230(7) -0.0232(6) F2 0.0445(7) 0.0385(6) 0.0506(7) -0.0189(5) 0.0023(6) -0.0003(5) F3 0.0628(9) 0.0411(7) 0.0391(7) 0.0038(5) -0.0067(6) -0.0048(6) F4 0.0581(8) 0.0323(6) 0.0659(9) -0.0049(6) -0.0106(7) 0.0098(6) F5 0.0659(9) 0.0527(8) 0.0592(8) -0.0180(6) -0.0152(7) -0.0251(7) F6 0.0447(7) 0.0370(6) 0.0416(6) 0.0021(5) 0.0078(5) -0.0067(5) C1 0.0305(10) 0.0435(11) 0.0563(13) -0.0072(10) -0.0148(9) 0.0114(8) C2 0.0210(7) 0.0279(8) 0.0190(7) -0.0004(6) -0.0026(6) -0.0002(6) C3 0.0231(9) 0.0479(11) 0.0432(11) 0.0111(9) 0.0088(8) 0.0004(8) C4 0.0194(8) 0.0450(11) 0.0476(11) 0.0091(9) 0.0067(8) 0.0051(8) C5 0.0308(9) 0.0311(8) 0.0212(7) 0.0058(6) -0.0018(6) -0.0009(7) C6 0.0357(10) 0.0377(9) 0.0219(8) 0.0040(7) -0.0034(7) -0.0061(8) C7 0.0640(15) 0.0345(10) 0.0295(9) 0.0011(8) -0.0081(9) -0.0029(9) C8 0.0724(16) 0.0364(11) 0.0333(10) 0.0024(8) -0.0148(10) 0.0111(10) C9 0.0655(15) 0.0440(11) 0.0281(9) 0.0020(8) -0.0206(10) 0.0057(10) C10 0.0484(12) 0.0361(9) 0.0230(8) 0.0004(7) -0.0079(8) -0.0024(8) C11 0.0364(10) 0.0508(12) 0.0299(9) 0.0025(8) -0.0070(8) -0.0125(9) C12 0.128(3) 0.0442(14) 0.0580(16) 0.0021(12) -0.0387(18) 0.0269(16) C13 0.0853(19) 0.0411(11) 0.0330(10) -0.0017(9) -0.0206(11) -0.0069(12) C14 0.0195(8) 0.0257(8) 0.0322(8) 0.0048(6) -0.0040(6) 0.0007(6) C15 0.0196(8) 0.0281(8) 0.0328(8) 0.0034(7) -0.0074(6) -0.0032(6) C16 0.0281(9) 0.0356(9) 0.0358(9) 0.0090(7) -0.0090(7) -0.0072(7) C17 0.0299(10) 0.0318(9) 0.0514(12) 0.0129(8) -0.0115(8) -0.0070(7) C18 0.0346(10) 0.0257(9) 0.0558(12) 0.0004(8) -0.0128(9) -0.0035(7) C19 0.0271(9) 0.0311(9) 0.0396(10) -0.0029(7) -0.0091(7) 0.0031(7) C20 0.0312(9) 0.0308(9) 0.0353(9) -0.0004(7) -0.0102(7) -0.0062(7) C21 0.0451(12) 0.0379(11) 0.0656(15) 0.0205(10) -0.0130(11) -0.0138(9) C22 0.0471(13) 0.0451(12) 0.0465(12) -0.0148(9) -0.0088(10) 0.0067(10) C23 0.0358(10) 0.0330(9) 0.0417(10) -0.0084(8) 0.0064(8) -0.0099(8) C24 0.0370(10) 0.0290(9) 0.0392(10) -0.0082(7) -0.0061(8) -0.0033(8) Cl1 0.0435(16) 0.0738(17) 0.0552(18) 0.0224(13) 0.0057(13) 0.0015(12) Cl2 0.120(5) 0.056(2) 0.236(9) -0.043(4) 0.080(6) -0.012(3) Cl1A 0.206(10) 0.104(5) 0.154(9) 0.017(5) 0.137(8) 0.032(5) Cl2A 0.144(9) 0.079(5) 0.136(8) -0.052(5) 0.074(6) -0.050(5) Cl1B 0.111(4) 0.072(4) 0.083(3) -0.020(3) 0.052(3) -0.044(4) Cl2B 0.140(7) 0.074(4) 0.077(3) -0.008(3) 0.040(3) -0.029(4) Cl1C 0.127(5) 0.188(8) 0.115(5) -0.025(5) 0.034(4) -0.008(4) Cl2C 0.119(6) 0.47(2) 0.111(7) 0.135(12) -0.023(5) -0.052(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 In C1 2.1153(19) . ? In C2 2.1823(16) . ? In O3 2.1854(12) 2_755 ? In O4 2.2506(12) . ? In O1 2.4292(12) . ? S1 O2 1.4232(14) . ? S1 O1 1.4464(12) . ? S1 O3 1.4743(12) . ? S1 C23 1.833(2) . ? S2 O5 1.4307(14) . ? S2 O6 1.4309(14) . ? S2 O4 1.4710(13) . ? S2 C24 1.823(2) . ? N1 C2 1.349(2) . ? N1 C3 1.381(2) . ? N1 C5 1.451(2) . ? N2 C2 1.350(2) . ? N2 C4 1.383(2) . ? N2 C14 1.447(2) . ? O3 In 2.1854(12) 2_755 ? F1 C23 1.329(2) . ? F2 C23 1.325(2) . ? F3 C23 1.321(3) . ? F4 C24 1.324(2) . ? F5 C24 1.328(2) . ? F6 C24 1.331(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C4 1.345(3) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C10 1.390(3) . ? C5 C6 1.393(3) . ? C6 C7 1.388(3) . ? C6 C11 1.504(3) . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 C12 1.515(3) . ? C9 C10 1.400(3) . ? C9 H9 0.9500 . ? C10 C13 1.505(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.391(3) . ? C14 C15 1.396(2) . ? C15 C16 1.395(2) . ? C15 C20 1.500(2) . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.384(3) . ? C17 C21 1.510(3) . ? C18 C19 1.392(3) . ? C18 H18 0.9500 . ? C19 C22 1.508(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C25 Cl2 1.738(8) . ? C25 Cl1 1.771(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C25A Cl2A 1.732(9) . ? C25A Cl1A 1.736(9) . ? C25A H25C 0.9900 . ? C25A H25D 0.9900 . ? C25B Cl2B 1.739(8) . ? C25B Cl1B 1.774(8) . ? C25B H25E 0.9900 . ? C25B H25F 0.9900 . ? C25C Cl1C 1.770(10) . ? C25C Cl2C 1.778(10) . ? C25C H25G 0.9900 . ? C25C H25H 0.9900 . ? Cl1C Cl1C 1.660(15) 2_846 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 In C2 138.02(8) . . ? C1 In O3 113.79(7) . 2_755 ? C2 In O3 106.54(5) . 2_755 ? C1 In O4 105.37(7) . . ? C2 In O4 88.00(5) . . ? O3 In O4 86.25(5) 2_755 . ? C1 In O1 92.35(7) . . ? C2 In O1 84.28(5) . . ? O3 In O1 78.71(4) 2_755 . ? O4 In O1 160.34(5) . . ? O2 S1 O1 116.11(8) . . ? O2 S1 O3 114.42(8) . . ? O1 S1 O3 112.51(7) . . ? O2 S1 C23 106.72(9) . . ? O1 S1 C23 102.71(9) . . ? O3 S1 C23 102.43(8) . . ? O5 S2 O6 117.07(9) . . ? O5 S2 O4 113.32(8) . . ? O6 S2 O4 113.84(8) . . ? O5 S2 C24 104.01(10) . . ? O6 S2 C24 104.59(9) . . ? O4 S2 C24 101.72(8) . . ? C2 N1 C3 110.56(14) . . ? C2 N1 C5 123.62(14) . . ? C3 N1 C5 125.74(15) . . ? C2 N2 C4 110.22(14) . . ? C2 N2 C14 125.11(14) . . ? C4 N2 C14 124.57(14) . . ? S1 O1 In 143.16(8) . . ? S1 O3 In 125.44(7) . 2_755 ? S2 O4 In 133.10(8) . . ? In C1 H1A 109.5 . . ? In C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 105.47(14) . . ? N1 C2 In 122.44(11) . . ? N2 C2 In 132.03(12) . . ? C4 C3 N1 106.69(16) . . ? C4 C3 H3 126.7 . . ? N1 C3 H3 126.7 . . ? C3 C4 N2 107.05(16) . . ? C3 C4 H4 126.5 . . ? N2 C4 H4 126.5 . . ? C10 C5 C6 123.31(16) . . ? C10 C5 N1 118.82(16) . . ? C6 C5 N1 117.87(16) . . ? C7 C6 C5 117.15(17) . . ? C7 C6 C11 121.09(18) . . ? C5 C6 C11 121.76(17) . . ? C6 C7 C8 121.9(2) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 118.94(19) . . ? C9 C8 C12 120.5(2) . . ? C7 C8 C12 120.5(2) . . ? C8 C9 C10 121.82(19) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C5 C10 C9 116.89(18) . . ? C5 C10 C13 123.00(18) . . ? C9 C10 C13 120.11(18) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 123.32(16) . . ? C19 C14 N2 119.21(16) . . ? C15 C14 N2 117.46(15) . . ? C16 C15 C14 117.01(17) . . ? C16 C15 C20 121.03(17) . . ? C14 C15 C20 121.94(15) . . ? C17 C16 C15 121.66(19) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 118.89(17) . . ? C18 C17 C21 120.9(2) . . ? C16 C17 C21 120.2(2) . . ? C17 C18 C19 122.14(19) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C14 C19 C18 116.91(18) . . ? C14 C19 C22 121.97(18) . . ? C18 C19 C22 121.11(19) . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? F3 C23 F2 109.09(17) . . ? F3 C23 F1 108.37(17) . . ? F2 C23 F1 108.57(16) . . ? F3 C23 S1 110.69(13) . . ? F2 C23 S1 110.72(14) . . ? F1 C23 S1 109.34(15) . . ? F4 C24 F5 108.49(16) . . ? F4 C24 F6 108.21(16) . . ? F5 C24 F6 107.78(17) . . ? F4 C24 S2 111.72(14) . . ? F5 C24 S2 109.88(14) . . ? F6 C24 S2 110.65(12) . . ? Cl2 C25 Cl1 110.3(6) . . ? Cl2 C25 H25A 109.6 . . ? Cl1 C25 H25A 109.6 . . ? Cl2 C25 H25B 109.6 . . ? Cl1 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? Cl2A C25A Cl1A 118.0(7) . . ? Cl2A C25A H25C 107.8 . . ? Cl1A C25A H25C 107.8 . . ? Cl2A C25A H25D 107.8 . . ? Cl1A C25A H25D 107.8 . . ? H25C C25A H25D 107.1 . . ? Cl2B C25B Cl1B 114.1(6) . . ? Cl2B C25B H25E 108.7 . . ? Cl1B C25B H25E 108.7 . . ? Cl2B C25B H25F 108.7 . . ? Cl1B C25B H25F 108.7 . . ? H25E C25B H25F 107.6 . . ? Cl1C C25C Cl2C 109.0(7) . . ? Cl1C C25C H25G 109.9 . . ? Cl2C C25C H25G 109.9 . . ? Cl1C C25C H25H 109.9 . . ? Cl2C C25C H25H 109.9 . . ? H25G C25C H25H 108.3 . . ? Cl1C Cl1C C25C 142.2(10) 2_846 . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.09 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.394 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.065 #=== END data_h03asw15 _database_code_depnum_ccdc_archive 'CCDC 234197' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 2' _chemical_melting_point ? _chemical_formula_moiety 'C25 H32 Cl2 F3 In N2 O3 S' _chemical_formula_sum 'C25 H32 Cl2 F3 In N2 O3 S' _chemical_formula_weight 683.31 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' In In -0.7276 1.3100 '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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 9.06100(10) _cell_length_b 22.3800(3) _cell_length_c 14.7900(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.9230(10) _cell_angle_gamma 90.00 _cell_volume 2944.86(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 154693 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 1.102 _exptl_absorpt_correction_type sortav _exptl_absorpt_correction_T_min 0.6087 _exptl_absorpt_correction_T_max 0.9170 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 49531 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.38 _reflns_number_total 6651 _reflns_number_gt 5160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Nonius program suite version 1.9 (1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119. ; _computing_structure_refinement ; SHELX97-2 Program for Crystal Structure Analysis. G. M. Sheldrick, Institut f. Anorg. Chemie der Universitat, Tammanstrasse 4, D-3400 Gottingen, Germany, 1998. ; _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565 ; _computing_publication_material 'SHELX97-2, G. M. Sheldrick' _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^)+(0.0371P)^2^+1.6718P] 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 6651 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 In In 0.731723(17) 0.251469(6) 0.055306(11) 0.02327(6) Uani 1 1 d . . . S S 0.66763(6) 0.25686(2) 0.30304(4) 0.02393(12) Uani 1 1 d . . . O1 O 0.7572(2) 0.25957(7) 0.23211(12) 0.0334(4) Uani 1 1 d . . . O2 O 0.75617(19) 0.26641(7) 0.39457(11) 0.0299(4) Uani 1 1 d . . . O3 O 0.55824(19) 0.21014(7) 0.29466(12) 0.0358(4) Uani 1 1 d . . . F1 F 0.6363(2) 0.37321(7) 0.30050(15) 0.0687(6) Uani 1 1 d . . . F2 F 0.48455(18) 0.32733(7) 0.19400(11) 0.0494(4) Uani 1 1 d . . . F3 F 0.4478(2) 0.32519(8) 0.33300(12) 0.0582(5) Uani 1 1 d . . . N1 N 1.0988(2) 0.24833(7) 0.11951(14) 0.0243(4) Uani 1 1 d . . . N2 N 1.0092(2) 0.16091(8) 0.13018(13) 0.0249(4) Uani 1 1 d . . . C1 C 0.7219(3) 0.34661(10) 0.03911(19) 0.0381(6) Uani 1 1 d . . . H1A H 0.6185 0.3586 0.0133 0.057 Uiso 1 1 calc R . . H1B H 0.7883 0.3590 -0.0026 0.057 Uiso 1 1 calc R . . H1C H 0.7542 0.3657 0.0992 0.057 Uiso 1 1 calc R . . C2 C 0.5691(3) 0.18187(10) 0.05328(17) 0.0314(5) Uani 1 1 d . . . H2A H 0.5670 0.1693 0.1165 0.047 Uiso 1 1 calc R . . H2B H 0.5962 0.1478 0.0182 0.047 Uiso 1 1 calc R . . H2C H 0.4696 0.1967 0.0242 0.047 Uiso 1 1 calc R . . C3 C 0.9692(2) 0.21701(9) 0.10050(15) 0.0223(4) Uani 1 1 d . . . C4 C 1.2178(3) 0.21249(11) 0.15996(17) 0.0325(5) Uani 1 1 d . . . H4 H 1.3195 0.2244 0.1792 0.039 Uiso 1 1 calc R . . C5 C 1.1614(3) 0.15760(11) 0.16659(18) 0.0340(6) Uani 1 1 d . . . H5 H 1.2154 0.1231 0.1915 0.041 Uiso 1 1 calc R . . C6 C 1.1189(2) 0.31021(9) 0.09474(16) 0.0245(5) Uani 1 1 d . . . C7 C 1.1554(3) 0.32171(10) 0.00883(16) 0.0290(5) Uani 1 1 d . . . C8 C 1.1838(3) 0.38063(11) -0.01187(17) 0.0358(6) Uani 1 1 d . . . H8 H 1.2100 0.3896 -0.0696 0.043 Uiso 1 1 calc R . . C9 C 1.1749(3) 0.42691(11) 0.04989(18) 0.0380(6) Uani 1 1 d . . . C10 C 1.1371(3) 0.41333(11) 0.13351(17) 0.0338(6) Uani 1 1 d . . . H10 H 1.1293 0.4448 0.1754 0.041 Uiso 1 1 calc R . . C11 C 1.1099(3) 0.35503(10) 0.15872(16) 0.0284(5) Uani 1 1 d . . . C12 C 1.1627(3) 0.27258(12) -0.06033(18) 0.0386(6) Uani 1 1 d . . . H12A H 1.0607 0.2594 -0.0871 0.058 Uiso 1 1 calc R . . H12B H 1.2202 0.2388 -0.0295 0.058 Uiso 1 1 calc R . . H12C H 1.2121 0.2877 -0.1092 0.058 Uiso 1 1 calc R . . C13 C 1.2064(4) 0.49101(12) 0.0251(2) 0.0577(9) Uani 1 1 d . . . H13A H 1.1825 0.5181 0.0724 0.087 Uiso 1 1 calc R . . H13B H 1.1441 0.5012 -0.0346 0.087 Uiso 1 1 calc R . . H13C H 1.3128 0.4951 0.0215 0.087 Uiso 1 1 calc R . . C14 C 1.0733(3) 0.34158(12) 0.25115(17) 0.0375(6) Uani 1 1 d . . . H14A H 0.9713 0.3252 0.2433 0.056 Uiso 1 1 calc R . . H14B H 1.0793 0.3784 0.2875 0.056 Uiso 1 1 calc R . . H14C H 1.1452 0.3123 0.2832 0.056 Uiso 1 1 calc R . . C15 C 0.9130(2) 0.10876(9) 0.11657(16) 0.0250(5) Uani 1 1 d . . . C16 C 0.8495(3) 0.08754(10) 0.18902(17) 0.0299(5) Uani 1 1 d . . . C17 C 0.7592(3) 0.03681(11) 0.17179(19) 0.0360(6) Uani 1 1 d . . . H17 H 0.7127 0.0218 0.2196 0.043 Uiso 1 1 calc R . . C18 C 0.7345(3) 0.00752(10) 0.0879(2) 0.0373(6) Uani 1 1 d . . . C19 C 0.8028(3) 0.02996(10) 0.01856(19) 0.0340(6) Uani 1 1 d . . . H19 H 0.7873 0.0100 -0.0392 0.041 Uiso 1 1 calc R . . C20 C 0.8930(3) 0.08057(10) 0.03088(16) 0.0280(5) Uani 1 1 d . . . C21 C 0.8773(3) 0.11651(12) 0.28252(18) 0.0411(6) Uani 1 1 d . . . H21A H 0.7850 0.1153 0.3079 0.062 Uiso 1 1 calc R . . H21B H 0.9079 0.1581 0.2770 0.062 Uiso 1 1 calc R . . H21C H 0.9573 0.0949 0.3236 0.062 Uiso 1 1 calc R . . C22 C 0.6367(3) -0.04775(12) 0.0724(2) 0.0531(8) Uani 1 1 d . . . H22A H 0.6331 -0.0625 0.0096 0.080 Uiso 1 1 calc R . . H22B H 0.5348 -0.0378 0.0807 0.080 Uiso 1 1 calc R . . H22C H 0.6789 -0.0787 0.1167 0.080 Uiso 1 1 calc R . . C23 C 0.9662(3) 0.10362(10) -0.04541(17) 0.0338(5) Uani 1 1 d . . . H23A H 0.9576 0.0735 -0.0943 0.051 Uiso 1 1 calc R . . H23B H 1.0726 0.1118 -0.0212 0.051 Uiso 1 1 calc R . . H23C H 0.9161 0.1405 -0.0704 0.051 Uiso 1 1 calc R . . C24 C 0.5535(3) 0.32454(11) 0.28152(19) 0.0376(6) Uani 1 1 d . . . C25 C 0.3817(4) -0.00378(14) 0.3048(3) 0.0627(9) Uani 1 1 d . . . H25A H 0.3994 -0.0258 0.3640 0.075 Uiso 1 1 calc R . . H25B H 0.4334 -0.0256 0.2616 0.075 Uiso 1 1 calc R . . Cl1 Cl 0.45790(8) 0.06845(3) 0.32267(6) 0.0586(2) Uani 1 1 d . . . Cl2 Cl 0.18770(9) -0.00167(3) 0.25983(6) 0.0550(2) 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 In 0.02344(10) 0.02261(9) 0.02312(9) 0.00154(6) 0.00277(6) 0.00096(6) S 0.0245(3) 0.0264(3) 0.0207(3) -0.0012(2) 0.0040(2) -0.0004(2) O1 0.0324(10) 0.0448(10) 0.0241(9) -0.0008(7) 0.0084(7) -0.0003(7) O2 0.0309(9) 0.0369(9) 0.0212(9) -0.0012(7) 0.0029(7) 0.0000(7) O3 0.0335(9) 0.0316(9) 0.0416(10) 0.0001(8) 0.0055(8) -0.0080(7) F1 0.0647(12) 0.0266(8) 0.1021(16) 0.0013(9) -0.0169(11) -0.0027(8) F2 0.0452(9) 0.0574(10) 0.0409(9) 0.0133(8) -0.0041(7) 0.0110(7) F3 0.0530(11) 0.0691(12) 0.0548(11) -0.0038(9) 0.0163(9) 0.0288(9) N1 0.0255(9) 0.0229(9) 0.0236(10) 0.0008(7) 0.0023(8) -0.0013(7) N2 0.0245(10) 0.0248(9) 0.0246(10) 0.0034(8) 0.0027(8) 0.0010(7) C1 0.0472(16) 0.0251(12) 0.0408(15) 0.0037(11) 0.0054(12) 0.0025(10) C2 0.0282(12) 0.0347(12) 0.0319(13) -0.0004(10) 0.0069(10) -0.0032(10) C3 0.0262(11) 0.0224(11) 0.0184(11) 0.0010(8) 0.0049(9) -0.0017(8) C4 0.0239(12) 0.0338(13) 0.0372(14) 0.0027(11) -0.0011(10) 0.0000(9) C5 0.0282(13) 0.0309(12) 0.0400(15) 0.0067(11) -0.0013(11) 0.0042(10) C6 0.0248(11) 0.0222(10) 0.0252(12) 0.0002(9) 0.0017(9) -0.0041(8) C7 0.0288(12) 0.0326(12) 0.0250(12) -0.0029(10) 0.0037(10) -0.0047(9) C8 0.0440(15) 0.0384(13) 0.0244(13) 0.0031(10) 0.0053(11) -0.0114(11) C9 0.0456(15) 0.0303(13) 0.0346(14) 0.0022(10) -0.0012(12) -0.0115(11) C10 0.0396(14) 0.0290(12) 0.0313(13) -0.0081(10) 0.0029(11) -0.0051(10) C11 0.0291(12) 0.0286(12) 0.0273(12) -0.0035(9) 0.0048(10) -0.0042(9) C12 0.0493(16) 0.0395(14) 0.0293(14) -0.0073(11) 0.0133(12) -0.0053(12) C13 0.084(2) 0.0351(15) 0.0503(19) 0.0069(14) 0.0036(17) -0.0210(15) C14 0.0450(15) 0.0407(14) 0.0283(14) -0.0068(11) 0.0112(11) -0.0082(11) C15 0.0227(11) 0.0203(10) 0.0313(13) 0.0063(9) 0.0031(9) 0.0015(8) C16 0.0281(12) 0.0295(12) 0.0321(13) 0.0096(10) 0.0059(10) 0.0069(9) C17 0.0321(13) 0.0304(13) 0.0473(16) 0.0170(12) 0.0122(12) 0.0028(10) C18 0.0302(13) 0.0233(11) 0.0566(17) 0.0090(12) 0.0037(12) 0.0002(9) C19 0.0359(14) 0.0241(11) 0.0400(15) -0.0002(10) 0.0020(11) -0.0001(10) C20 0.0271(12) 0.0238(11) 0.0324(13) 0.0046(9) 0.0043(10) 0.0034(9) C21 0.0486(16) 0.0447(15) 0.0317(14) 0.0088(12) 0.0122(12) 0.0046(12) C22 0.0407(16) 0.0308(14) 0.085(2) 0.0132(14) 0.0052(15) -0.0092(11) C23 0.0415(14) 0.0276(12) 0.0338(14) 0.0003(10) 0.0109(11) 0.0008(10) C24 0.0353(14) 0.0352(13) 0.0390(15) -0.0001(11) -0.0010(12) 0.0032(11) C25 0.0528(19) 0.0423(17) 0.089(3) -0.0075(17) 0.0030(18) 0.0068(14) Cl1 0.0418(4) 0.0506(4) 0.0806(6) -0.0156(4) 0.0042(4) 0.0014(3) Cl2 0.0571(5) 0.0474(4) 0.0583(5) -0.0084(3) 0.0054(4) -0.0092(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 In C2 2.141(2) . ? In C1 2.143(2) . ? In C3 2.264(2) . ? In O2 2.4617(16) 4_565 ? In O1 2.5876(18) . ? S O3 1.4299(17) . ? S O1 1.4441(18) . ? S O2 1.4528(17) . ? S C24 1.828(3) . ? O2 In 2.4617(16) 4_566 ? F1 C24 1.322(3) . ? F2 C24 1.328(3) . ? F3 C24 1.332(3) . ? N1 C3 1.351(3) . ? N1 C4 1.385(3) . ? N1 C6 1.453(3) . ? N2 C3 1.357(3) . ? N2 C5 1.384(3) . ? N2 C15 1.447(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C4 C5 1.341(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C11 1.392(3) . ? C6 C7 1.396(3) . ? C7 C8 1.389(3) . ? C7 C12 1.512(3) . ? C8 C9 1.393(4) . ? C8 H8 0.9500 . ? C9 C10 1.378(4) . ? C9 C13 1.521(3) . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 C14 1.497(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.392(3) . ? C15 C20 1.396(3) . ? C16 C17 1.395(3) . ? C16 C21 1.505(4) . ? C17 C18 1.383(4) . ? C17 H17 0.9500 . ? C18 C19 1.388(4) . ? C18 C22 1.514(3) . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 C23 1.504(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 Cl1 1.758(3) . ? C25 Cl2 1.758(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 In C1 135.03(10) . . ? C2 In C3 111.69(8) . . ? C1 In C3 112.87(9) . . ? C2 In O2 93.21(8) . 4_565 ? C1 In O2 93.61(8) . 4_565 ? C3 In O2 88.59(7) . 4_565 ? C2 In O1 89.69(8) . . ? C1 In O1 92.13(8) . . ? C3 In O1 80.07(7) . . ? O2 In O1 168.57(6) 4_565 . ? O3 S O1 116.34(11) . . ? O3 S O2 116.08(10) . . ? O1 S O2 112.55(11) . . ? O3 S C24 103.34(11) . . ? O1 S C24 102.48(12) . . ? O2 S C24 103.58(11) . . ? S O1 In 140.92(11) . . ? S O2 In 137.83(10) . 4_566 ? C3 N1 C4 111.36(18) . . ? C3 N1 C6 125.99(19) . . ? C4 N1 C6 122.45(19) . . ? C3 N2 C5 111.15(18) . . ? C3 N2 C15 125.76(18) . . ? C5 N2 C15 122.68(18) . . ? In C1 H1A 109.5 . . ? In C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? In C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? In C2 H2A 109.5 . . ? In C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? In C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 N2 104.15(18) . . ? N1 C3 In 128.67(15) . . ? N2 C3 In 126.26(15) . . ? C5 C4 N1 106.6(2) . . ? C5 C4 H4 126.7 . . ? N1 C4 H4 126.7 . . ? C4 C5 N2 106.7(2) . . ? C4 C5 H5 126.6 . . ? N2 C5 H5 126.6 . . ? C11 C6 C7 122.7(2) . . ? C11 C6 N1 119.3(2) . . ? C7 C6 N1 117.88(19) . . ? C8 C7 C6 117.5(2) . . ? C8 C7 C12 120.5(2) . . ? C6 C7 C12 122.0(2) . . ? C7 C8 C9 121.7(2) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 118.6(2) . . ? C10 C9 C13 120.9(2) . . ? C8 C9 C13 120.4(2) . . ? C9 C10 C11 122.3(2) . . ? C9 C10 H10 118.9 . . ? C11 C10 H10 118.9 . . ? C10 C11 C6 117.2(2) . . ? C10 C11 C14 120.9(2) . . ? C6 C11 C14 121.8(2) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 122.9(2) . . ? C16 C15 N2 119.6(2) . . ? C20 C15 N2 117.5(2) . . ? C15 C16 C17 116.8(2) . . ? C15 C16 C21 122.6(2) . . ? C17 C16 C21 120.6(2) . . ? C18 C17 C16 122.6(2) . . ? C18 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? C17 C18 C19 118.2(2) . . ? C17 C18 C22 120.9(3) . . ? C19 C18 C22 120.9(3) . . ? C20 C19 C18 122.1(2) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C15 117.4(2) . . ? C19 C20 C23 120.9(2) . . ? C15 C20 C23 121.7(2) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? F1 C24 F2 108.1(2) . . ? F1 C24 F3 108.1(2) . . ? F2 C24 F3 107.5(2) . . ? F1 C24 S 111.46(18) . . ? F2 C24 S 110.79(18) . . ? F3 C24 S 110.73(18) . . ? Cl1 C25 Cl2 111.60(17) . . ? Cl1 C25 H25A 109.3 . . ? Cl2 C25 H25A 109.3 . . ? Cl1 C25 H25B 109.3 . . ? Cl2 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.433 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.100 #=== END