# ic980671m.cif _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H32 In N S3' _chemical_formula_weight 461.44 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' 'S' 'S' 0.1246 0.1234 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1490(5) _cell_length_b 24.3811(13) _cell_length_c 18.8484(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.8100(10) _cell_angle_gamma 90.00 _cell_volume 4509.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 23.38 _exptl_crystal_description 'thick plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 1.324 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.982 _publ_section_experimental ; All measurements were made with a Siemens SMART platform diffractometer equipped with a 1K CCD area detector. A hemisphere of data (1271 frames at 5 cm detector distance) was collected using a narrow-frame method with scan widths of 0.30\% in omega an an exposure time of 15 s/frame. The first 50 frames were re-measured at the end of data collection to monitor instrument and crystal stability, and the maximum correction on I was <1%. The data were integrated using the Siemens SAINT program, with the intensities corrected for Lorentz factor, polarization, air absorption, and absorption due to variation in the path length through the detector faceplate. A psi scan absorption correction was applied based on the entire data set. Redundant reflections were averaged. Final cell constants were refined using 8192 reflections having I>10\s(I), and these, along with other information pertinent to data collection and refinement, are listed in Table 1. The Laue symmetry was determined to be 2/m, and from the systematic absences noted the space group was shown unambiguously to be P2(1)/c. ; _publ_section_figure_captions ; Fig. 1 -- View of molecule 1 (In1) showing the atom labels for the core atoms. Thermal ellipsoids are 40% equiprobability envelopes, with hydrogens omitted. Fig. 2 -- View of molecule 2 (In2) showing the atom labels for the core atoms. Thermal ellipsoids are 40% equiprobability envelopes, with hydrogens omitted. Fig. 3 -- Packing of the molecules in the unit cell. ; _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 19554 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 23.28 _reflns_number_total 6429 _reflns_number_gt 5850 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Siemens SMART software (Siemens, 1996)' _computing_data_reduction 'Siemens SMART software (Siemens, 1996)' _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^ > 4sigma(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^)+(0.0113P)^2^+3.7711P] 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_number_reflns 6429 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0460 _refine_ls_wR_factor_gt 0.0454 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group In1 In 0.399845(16) 0.690856(6) 0.080743(9) 0.03112(5) Uani 1 1 d . . . In2 In 0.844855(16) 0.948876(6) 0.185007(9) 0.03005(5) Uani 1 1 d . . . S1 S 0.23040(7) 0.73061(2) -0.02019(4) 0.04314(16) Uani 1 1 d . . . S2 S 0.38510(7) 0.59284(2) 0.09612(3) 0.04355(16) Uani 1 1 d . . . S3 S 0.47547(10) 0.74734(3) 0.18941(4) 0.0609(2) Uani 1 1 d . . . S4 S 0.77633(7) 1.00527(3) 0.07619(3) 0.04374(16) Uani 1 1 d . . . S5 S 0.99420(7) 0.98963(2) 0.29349(3) 0.04244(16) Uani 1 1 d . . . S6 S 0.87503(6) 0.85218(2) 0.16479(3) 0.03680(14) Uani 1 1 d . . . N1 N 0.59735(19) 0.69421(8) 0.04127(11) 0.0358(5) Uani 1 1 d . . . N2 N 0.64592(19) 0.94379(8) 0.22276(11) 0.0338(4) Uani 1 1 d . . . C1 C 0.2229(2) 0.80508(9) -0.00270(13) 0.0343(5) Uani 1 1 d . . . C2 C 0.3629(3) 0.83107(11) 0.00962(18) 0.0538(7) Uani 1 1 d . . . H2A H 0.3987 0.8241 -0.0325 0.081 Uiso 1 1 calc R . . H2B H 0.4237 0.8154 0.0532 0.081 Uiso 1 1 calc R . . H2C H 0.3557 0.8703 0.0161 0.081 Uiso 1 1 calc R . . C3 C 0.1274(3) 0.82825(11) -0.07211(16) 0.0571(8) Uani 1 1 d . . . H3A H 0.1646 0.8211 -0.1137 0.086 Uiso 1 1 calc R . . H3B H 0.1179 0.8675 -0.0667 0.086 Uiso 1 1 calc R . . H3C H 0.0388 0.8109 -0.0801 0.086 Uiso 1 1 calc R . . C4 C 0.1663(3) 0.81594(12) 0.06312(16) 0.0535(7) Uani 1 1 d . . . H4A H 0.0769 0.7993 0.0550 0.080 Uiso 1 1 calc R . . H4B H 0.1589 0.8552 0.0696 0.080 Uiso 1 1 calc R . . H4C H 0.2269 0.8003 0.1067 0.080 Uiso 1 1 calc R . . C5 C 0.2570(3) 0.56355(10) 0.01652(13) 0.0379(6) Uani 1 1 d . . . C6 C 0.2956(3) 0.57540(13) -0.05442(14) 0.0542(7) Uani 1 1 d . . . H6A H 0.3858 0.5609 -0.0515 0.081 Uiso 1 1 calc R . . H6B H 0.2954 0.6147 -0.0623 0.081 Uiso 1 1 calc R . . H6C H 0.2302 0.5581 -0.0949 0.081 Uiso 1 1 calc R . . C7 C 0.2601(4) 0.50190(11) 0.03110(18) 0.0659(9) Uani 1 1 d . . . H7A H 0.3504 0.4878 0.0333 0.099 Uiso 1 1 calc R . . H7B H 0.1939 0.4838 -0.0082 0.099 Uiso 1 1 calc R . . H7C H 0.2381 0.4950 0.0774 0.099 Uiso 1 1 calc R . . C8 C 0.1162(3) 0.58594(13) 0.01312(19) 0.0628(8) Uani 1 1 d . . . H8A H 0.0928 0.5781 0.0589 0.094 Uiso 1 1 calc R . . H8B H 0.0501 0.5688 -0.0272 0.094 Uiso 1 1 calc R . . H8C H 0.1155 0.6253 0.0055 0.094 Uiso 1 1 calc R . . C9 C 0.5049(3) 0.70386(11) 0.27109(13) 0.0408(6) Uani 1 1 d . . . C10 C 0.6153(4) 0.66193(16) 0.2697(2) 0.0863(11) Uani 1 1 d . . . H10A H 0.6977 0.6808 0.2665 0.129 Uiso 1 1 calc R . . H10B H 0.5846 0.6381 0.2275 0.129 Uiso 1 1 calc R . . H10C H 0.6338 0.6402 0.3143 0.129 Uiso 1 1 calc R . . C11 C 0.5520(4) 0.74261(15) 0.33563(16) 0.0744(10) Uani 1 1 d . . . H11A H 0.6344 0.7612 0.3319 0.112 Uiso 1 1 calc R . . H11B H 0.5704 0.7219 0.3810 0.112 Uiso 1 1 calc R . . H11C H 0.4813 0.7695 0.3352 0.112 Uiso 1 1 calc R . . C12 C 0.3773(4) 0.67472(18) 0.2759(2) 0.0928(13) Uani 1 1 d . . . H12A H 0.3481 0.6502 0.2343 0.139 Uiso 1 1 calc R . . H12B H 0.3062 0.7014 0.2754 0.139 Uiso 1 1 calc R . . H12C H 0.3951 0.6537 0.3210 0.139 Uiso 1 1 calc R . . C13 C 0.6335(3) 0.65381(11) 0.00232(15) 0.0482(7) Uani 1 1 d . . . H13 H 0.5765 0.6229 -0.0089 0.058 Uiso 1 1 calc R . . C14 C 0.7493(3) 0.65501(11) -0.02210(16) 0.0530(7) Uani 1 1 d . . . H14 H 0.7707 0.6256 -0.0495 0.064 Uiso 1 1 calc R . . C15 C 0.8338(3) 0.69976(12) -0.00601(15) 0.0496(7) Uani 1 1 d . . . H15 H 0.9145 0.7016 -0.0217 0.060 Uiso 1 1 calc R . . C16 C 0.7974(3) 0.74157(13) 0.03335(17) 0.0571(8) Uani 1 1 d . . . H16 H 0.8524 0.7730 0.0445 0.069 Uiso 1 1 calc R . . C17 C 0.6798(3) 0.73733(11) 0.05655(16) 0.0496(7) Uani 1 1 d . . . H17 H 0.6569 0.7661 0.0844 0.060 Uiso 1 1 calc R . . C18 C 0.7414(2) 0.95871(10) -0.00416(13) 0.0353(5) Uani 1 1 d . . . C19 C 0.6279(3) 0.91864(12) -0.00113(16) 0.0523(7) Uani 1 1 d . . . H19A H 0.5473 0.9389 0.0020 0.078 Uiso 1 1 calc R . . H19B H 0.6573 0.8953 0.0416 0.078 Uiso 1 1 calc R . . H19C H 0.6067 0.8962 -0.0451 0.078 Uiso 1 1 calc R . . C20 C 0.6945(3) 0.99677(12) -0.07058(14) 0.0556(7) Uani 1 1 d . . . H20A H 0.6131 1.0163 -0.0671 0.083 Uiso 1 1 calc R . . H20B H 0.6746 0.9752 -0.1153 0.083 Uiso 1 1 calc R . . H20C H 0.7662 1.0229 -0.0714 0.083 Uiso 1 1 calc R . . C21 C 0.8687(3) 0.92794(12) -0.00908(15) 0.0498(7) Uani 1 1 d . . . H21A H 0.9400 0.9540 -0.0110 0.075 Uiso 1 1 calc R . . H21B H 0.8486 0.9055 -0.0531 0.075 Uiso 1 1 calc R . . H21C H 0.8991 0.9046 0.0337 0.075 Uiso 1 1 calc R . . C22 C 1.0375(2) 1.05981(9) 0.27007(13) 0.0334(5) Uani 1 1 d . . . C23 C 0.9097(3) 1.09528(11) 0.25272(16) 0.0502(7) Uani 1 1 d . . . H23A H 0.8697 1.0952 0.2943 0.075 Uiso 1 1 calc R . . H23B H 0.8445 1.0807 0.2099 0.075 Uiso 1 1 calc R . . H23C H 0.9334 1.1325 0.2429 0.075 Uiso 1 1 calc R . . C24 C 1.1389(3) 1.08124(11) 0.33865(14) 0.0475(7) Uani 1 1 d . . . H24A H 1.0969 1.0811 0.3795 0.071 Uiso 1 1 calc R . . H24B H 1.1655 1.1184 0.3300 0.071 Uiso 1 1 calc R . . H24C H 1.2189 1.0579 0.3502 0.071 Uiso 1 1 calc R . . C25 C 1.1010(3) 1.05966(13) 0.20547(15) 0.0544(7) Uani 1 1 d . . . H25A H 1.1823 1.0370 0.2170 0.082 Uiso 1 1 calc R . . H25B H 1.1252 1.0968 0.1955 0.082 Uiso 1 1 calc R . . H25C H 1.0363 1.0451 0.1626 0.082 Uiso 1 1 calc R . . C26 C 0.9718(3) 0.82115(10) 0.25234(13) 0.0377(6) Uani 1 1 d . . . C27 C 0.9107(3) 0.83686(13) 0.31516(15) 0.0598(8) Uani 1 1 d . . . H27A H 0.8161 0.8254 0.3038 0.090 Uiso 1 1 calc R . . H27B H 0.9159 0.8763 0.3219 0.090 Uiso 1 1 calc R . . H27C H 0.9611 0.8190 0.3598 0.090 Uiso 1 1 calc R . . C28 C 0.9606(4) 0.75942(11) 0.23885(18) 0.0686(9) Uani 1 1 d . . . H28A H 0.8657 0.7485 0.2281 0.103 Uiso 1 1 calc R . . H28B H 1.0118 0.7403 0.2823 0.103 Uiso 1 1 calc R . . H28C H 0.9973 0.7503 0.1976 0.103 Uiso 1 1 calc R . . C29 C 1.1199(3) 0.83896(13) 0.26931(16) 0.0566(7) Uani 1 1 d . . . H29A H 1.1580 0.8287 0.2290 0.085 Uiso 1 1 calc R . . H29B H 1.1708 0.8211 0.3139 0.085 Uiso 1 1 calc R . . H29C H 1.1255 0.8784 0.2759 0.085 Uiso 1 1 calc R . . C30 C 0.6035(3) 0.98634(10) 0.25562(15) 0.0439(6) Uani 1 1 d . . . H30 H 0.6585 1.0178 0.2655 0.053 Uiso 1 1 calc R . . C31 C 0.4823(3) 0.98582(12) 0.27556(16) 0.0513(7) Uani 1 1 d . . . H31 H 0.4553 1.0165 0.2985 0.062 Uiso 1 1 calc R . . C32 C 0.4015(3) 0.94007(12) 0.26157(16) 0.0521(7) Uani 1 1 d . . . H32 H 0.3181 0.9388 0.2746 0.062 Uiso 1 1 calc R . . C33 C 0.4451(3) 0.89603(11) 0.22803(17) 0.0540(7) Uani 1 1 d . . . H33 H 0.3919 0.8640 0.2179 0.065 Uiso 1 1 calc R . . C34 C 0.5669(3) 0.89923(10) 0.20951(15) 0.0448(6) Uani 1 1 d . . . H34 H 0.5959 0.8689 0.1866 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 In1 0.04031(10) 0.02362(9) 0.02708(9) -0.00130(6) 0.00431(7) -0.00127(7) In2 0.03485(9) 0.02604(9) 0.02736(9) -0.00030(6) 0.00447(7) -0.00172(6) S1 0.0509(4) 0.0287(3) 0.0401(4) -0.0029(3) -0.0061(3) 0.0033(3) S2 0.0637(4) 0.0248(3) 0.0329(3) 0.0026(3) -0.0045(3) -0.0049(3) S3 0.1112(7) 0.0320(4) 0.0320(4) -0.0057(3) 0.0048(4) -0.0091(4) S4 0.0644(4) 0.0305(3) 0.0302(3) 0.0023(3) 0.0010(3) 0.0006(3) S5 0.0557(4) 0.0306(3) 0.0316(3) 0.0039(3) -0.0062(3) -0.0079(3) S6 0.0492(4) 0.0273(3) 0.0313(3) -0.0016(2) 0.0054(3) 0.0024(3) N1 0.0353(11) 0.0313(11) 0.0382(12) -0.0026(9) 0.0046(9) 0.0009(9) N2 0.0350(11) 0.0314(11) 0.0337(11) -0.0035(8) 0.0065(9) -0.0039(8) C1 0.0345(13) 0.0271(12) 0.0411(14) 0.0019(10) 0.0091(11) 0.0026(10) C2 0.0501(16) 0.0407(15) 0.073(2) 0.0026(14) 0.0203(15) -0.0108(13) C3 0.0695(19) 0.0389(15) 0.0537(18) 0.0073(13) -0.0007(15) 0.0137(14) C4 0.0483(16) 0.0602(18) 0.0568(18) -0.0083(14) 0.0219(14) 0.0063(13) C5 0.0448(14) 0.0302(13) 0.0350(14) -0.0050(10) 0.0035(11) -0.0067(11) C6 0.0591(17) 0.0629(19) 0.0366(15) -0.0131(13) 0.0049(13) -0.0161(15) C7 0.091(2) 0.0330(15) 0.063(2) -0.0067(14) -0.0002(18) -0.0136(15) C8 0.0480(17) 0.0613(19) 0.079(2) -0.0145(17) 0.0155(16) -0.0107(14) C9 0.0449(14) 0.0482(15) 0.0284(13) -0.0017(11) 0.0076(11) -0.0113(12) C10 0.084(3) 0.085(3) 0.079(3) 0.015(2) 0.000(2) 0.025(2) C11 0.103(3) 0.084(2) 0.0325(16) -0.0135(16) 0.0112(17) -0.036(2) C12 0.091(3) 0.129(3) 0.070(2) -0.027(2) 0.041(2) -0.059(3) C13 0.0566(17) 0.0351(14) 0.0553(17) -0.0080(13) 0.0190(14) -0.0050(12) C14 0.0651(19) 0.0411(16) 0.0600(18) -0.0057(14) 0.0293(16) 0.0051(14) C15 0.0411(15) 0.0622(18) 0.0462(16) -0.0009(14) 0.0122(13) 0.0033(13) C16 0.0414(16) 0.0642(19) 0.068(2) -0.0251(16) 0.0178(15) -0.0170(14) C17 0.0421(15) 0.0485(16) 0.0580(18) -0.0211(14) 0.0123(13) -0.0077(12) C18 0.0376(13) 0.0394(14) 0.0282(13) -0.0008(10) 0.0075(11) -0.0013(11) C19 0.0476(16) 0.0573(18) 0.0505(17) -0.0104(14) 0.0100(13) -0.0143(13) C20 0.0663(19) 0.0644(19) 0.0328(14) 0.0082(13) 0.0066(14) 0.0138(15) C21 0.0489(16) 0.0583(17) 0.0462(16) 0.0090(14) 0.0197(13) 0.0101(13) C22 0.0367(13) 0.0314(13) 0.0308(13) -0.0014(10) 0.0062(10) -0.0060(10) C23 0.0600(17) 0.0363(15) 0.0506(17) 0.0028(12) 0.0075(14) 0.0116(13) C24 0.0537(16) 0.0459(15) 0.0398(15) -0.0049(12) 0.0066(13) -0.0167(13) C25 0.0489(16) 0.075(2) 0.0431(16) -0.0067(14) 0.0182(14) -0.0167(14) C26 0.0454(14) 0.0337(13) 0.0341(13) 0.0079(11) 0.0103(12) 0.0028(11) C27 0.076(2) 0.068(2) 0.0417(16) 0.0145(14) 0.0254(15) 0.0043(16) C28 0.100(3) 0.0317(15) 0.064(2) 0.0124(14) 0.0026(19) 0.0049(15) C29 0.0458(16) 0.071(2) 0.0481(17) 0.0004(15) 0.0038(14) 0.0018(14) C30 0.0410(14) 0.0372(14) 0.0532(16) -0.0158(12) 0.0113(13) -0.0108(11) C31 0.0465(16) 0.0500(17) 0.0604(18) -0.0242(14) 0.0191(14) -0.0071(13) C32 0.0454(16) 0.0573(18) 0.0589(18) -0.0140(14) 0.0232(14) -0.0115(13) C33 0.0495(16) 0.0415(16) 0.075(2) -0.0157(14) 0.0242(15) -0.0173(13) C34 0.0449(15) 0.0331(14) 0.0576(17) -0.0113(12) 0.0154(13) -0.0065(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 In1 N1 2.311(2) . ? In1 S2 2.4165(6) . ? In1 S1 2.4172(6) . ? In1 S3 2.4243(7) . ? In2 N2 2.3092(19) . ? In2 S4 2.4191(6) . ? In2 S6 2.4201(6) . ? In2 S5 2.4252(6) . ? S1 C1 1.850(2) . ? S2 C5 1.859(2) . ? S3 C9 1.830(3) . ? S4 C18 1.853(2) . ? S5 C22 1.848(2) . ? S6 C26 1.852(2) . ? N1 C17 1.329(3) . ? N1 C13 1.335(3) . ? N2 C30 1.335(3) . ? N2 C34 1.335(3) . ? C1 C2 1.518(3) . ? C1 C4 1.518(4) . ? C1 C3 1.524(3) . ? C5 C6 1.514(4) . ? C5 C8 1.516(4) . ? C5 C7 1.527(4) . ? C9 C12 1.500(4) . ? C9 C11 1.518(4) . ? C9 C10 1.522(4) . ? C13 C14 1.367(4) . ? C14 C15 1.373(4) . ? C15 C16 1.366(4) . ? C16 C17 1.376(4) . ? C18 C21 1.518(3) . ? C18 C19 1.522(3) . ? C18 C20 1.533(3) . ? C22 C25 1.516(3) . ? C22 C23 1.524(3) . ? C22 C24 1.524(3) . ? C26 C29 1.518(4) . ? C26 C27 1.519(4) . ? C26 C28 1.526(4) . ? C30 C31 1.374(4) . ? C31 C32 1.370(4) . ? C32 C33 1.376(4) . ? C33 C34 1.369(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 In1 S2 99.15(5) . . ? N1 In1 S1 103.51(5) . . ? S2 In1 S1 115.94(2) . . ? N1 In1 S3 97.96(5) . . ? S2 In1 S3 118.45(2) . . ? S1 In1 S3 116.43(2) . . ? N2 In2 S4 101.96(5) . . ? N2 In2 S6 98.74(5) . . ? S4 In2 S6 116.15(2) . . ? N2 In2 S5 99.75(5) . . ? S4 In2 S5 117.66(2) . . ? S6 In2 S5 117.06(2) . . ? C1 S1 In1 107.85(8) . . ? C5 S2 In1 109.58(8) . . ? C9 S3 In1 109.27(8) . . ? C18 S4 In2 107.35(8) . . ? C22 S5 In2 108.27(8) . . ? C26 S6 In2 108.50(8) . . ? C17 N1 C13 117.2(2) . . ? C17 N1 In1 120.56(16) . . ? C13 N1 In1 122.28(16) . . ? C30 N2 C34 118.0(2) . . ? C30 N2 In2 120.83(15) . . ? C34 N2 In2 121.12(16) . . ? C2 C1 C4 109.7(2) . . ? C2 C1 C3 110.0(2) . . ? C4 C1 C3 110.2(2) . . ? C2 C1 S1 110.95(17) . . ? C4 C1 S1 110.97(17) . . ? C3 C1 S1 104.88(17) . . ? C6 C5 C8 110.3(2) . . ? C6 C5 C7 110.4(2) . . ? C8 C5 C7 109.8(2) . . ? C6 C5 S2 110.74(17) . . ? C8 C5 S2 110.70(18) . . ? C7 C5 S2 104.76(18) . . ? C12 C9 C11 110.3(3) . . ? C12 C9 C10 109.5(3) . . ? C11 C9 C10 110.5(3) . . ? C12 C9 S3 111.6(2) . . ? C11 C9 S3 105.3(2) . . ? C10 C9 S3 109.7(2) . . ? N1 C13 C14 123.4(2) . . ? C13 C14 C15 119.0(3) . . ? C16 C15 C14 118.2(3) . . ? C15 C16 C17 119.5(3) . . ? N1 C17 C16 122.7(2) . . ? C21 C18 C19 110.4(2) . . ? C21 C18 C20 109.9(2) . . ? C19 C18 C20 109.8(2) . . ? C21 C18 S4 111.38(18) . . ? C19 C18 S4 110.56(17) . . ? C20 C18 S4 104.55(17) . . ? C25 C22 C23 110.0(2) . . ? C25 C22 C24 110.4(2) . . ? C23 C22 C24 109.9(2) . . ? C25 C22 S5 111.44(18) . . ? C23 C22 S5 109.58(17) . . ? C24 C22 S5 105.38(16) . . ? C29 C26 C27 110.1(2) . . ? C29 C26 C28 110.2(2) . . ? C27 C26 C28 110.5(2) . . ? C29 C26 S6 109.98(18) . . ? C27 C26 S6 111.24(18) . . ? C28 C26 S6 104.75(18) . . ? N2 C30 C31 122.5(2) . . ? C32 C31 C30 119.2(2) . . ? C31 C32 C33 118.5(2) . . ? C34 C33 C32 119.3(2) . . ? N2 C34 C33 122.5(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 N1 In1 S1 C1 -91.82(9) . . . . ? S2 In1 S1 C1 160.80(8) . . . . ? S3 In1 S1 C1 14.35(9) . . . . ? N1 In1 S2 C5 -101.53(10) . . . . ? S1 In1 S2 C5 8.44(9) . . . . ? S3 In1 S2 C5 154.18(9) . . . . ? N1 In1 S3 C9 -107.25(11) . . . . ? S2 In1 S3 C9 -2.28(10) . . . . ? S1 In1 S3 C9 143.30(9) . . . . ? N2 In2 S4 C18 -99.70(9) . . . . ? S6 In2 S4 C18 6.39(9) . . . . ? S5 In2 S4 C18 152.45(8) . . . . ? N2 In2 S5 C22 -111.99(9) . . . . ? S4 In2 S5 C22 -2.87(9) . . . . ? S6 In2 S5 C22 142.88(8) . . . . ? N2 In2 S6 C26 -87.65(10) . . . . ? S4 In2 S6 C26 164.35(8) . . . . ? S5 In2 S6 C26 18.08(9) . . . . ? S2 In1 N1 C17 -149.23(19) . . . . ? S1 In1 N1 C17 91.1(2) . . . . ? S3 In1 N1 C17 -28.6(2) . . . . ? S2 In1 N1 C13 31.1(2) . . . . ? S1 In1 N1 C13 -88.5(2) . . . . ? S3 In1 N1 C13 151.77(19) . . . . ? S4 In2 N2 C30 -75.42(19) . . . . ? S6 In2 N2 C30 165.34(18) . . . . ? S5 In2 N2 C30 45.77(19) . . . . ? S4 In2 N2 C34 101.57(19) . . . . ? S6 In2 N2 C34 -17.66(19) . . . . ? S5 In2 N2 C34 -137.23(19) . . . . ? In1 S1 C1 C2 54.8(2) . . . . ? In1 S1 C1 C4 -67.43(18) . . . . ? In1 S1 C1 C3 173.54(16) . . . . ? In1 S2 C5 C6 59.2(2) . . . . ? In1 S2 C5 C8 -63.5(2) . . . . ? In1 S2 C5 C7 178.22(17) . . . . ? In1 S3 C9 C12 -60.6(2) . . . . ? In1 S3 C9 C11 179.79(19) . . . . ? In1 S3 C9 C10 60.9(2) . . . . ? C17 N1 C13 C14 -0.1(4) . . . . ? In1 N1 C13 C14 179.5(2) . . . . ? N1 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 1.1(5) . . . . ? C13 N1 C17 C16 0.6(4) . . . . ? In1 N1 C17 C16 -179.0(2) . . . . ? C15 C16 C17 N1 -1.1(5) . . . . ? In2 S4 C18 C21 -63.06(18) . . . . ? In2 S4 C18 C19 60.14(19) . . . . ? In2 S4 C18 C20 178.29(15) . . . . ? In2 S5 C22 C25 -56.31(19) . . . . ? In2 S5 C22 C23 65.72(18) . . . . ? In2 S5 C22 C24 -176.05(15) . . . . ? In2 S6 C26 C29 -72.91(19) . . . . ? In2 S6 C26 C27 49.3(2) . . . . ? In2 S6 C26 C28 168.74(18) . . . . ? C34 N2 C30 C31 -0.4(4) . . . . ? In2 N2 C30 C31 176.7(2) . . . . ? N2 C30 C31 C32 0.2(4) . . . . ? C30 C31 C32 C33 0.2(5) . . . . ? C31 C32 C33 C34 -0.2(5) . . . . ? C30 N2 C34 C33 0.3(4) . . . . ? In2 N2 C34 C33 -176.8(2) . . . . ? C32 C33 C34 N2 0.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.856 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.043 data_k392 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H41 N4 S3 In, C H2 Cl2' _chemical_formula_sum 'C24 H43 Cl2 In N4 S3' _chemical_formula_weight 669.52 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' 'S' 'S' 0.1246 0.1234 '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.620(1) _cell_length_b 11.568(1) _cell_length_c 14.892(2) _cell_angle_alpha 79.54(1) _cell_angle_beta 75.88(1) _cell_angle_gamma 66.08(1) _cell_volume 1614.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 7.2 _cell_measurement_theta_max 12.25 _exptl_crystal_description 'Square column' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.110 _exptl_absorpt_correction_type none _publ_section_figure_captions ; Fig. 1 -- View of the molecule showing the atom numbering scheme for the core atoms. Thermal ellipsoids are 40% equiprobability envelopes, with hydrogens omitted. Fig. 2 -- Packing of the molecules in the unit cell. ; _diffrn_ambient_temperature 223(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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_decay_% 10.0 _diffrn_reflns_number 4465 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 22.53 _reflns_number_total 4201 _reflns_number_gt 3517 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^ > 4sigma(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^)+(0.0200P)^2^+1.6000P] 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_number_reflns 4201 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.459 _refine_ls_shift/su_mean 0.017 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 0.87625(3) 0.18687(2) 0.229470(18) 0.02937(10) Uani 1 1 d . . . S1 S 0.86414(11) 0.15374(10) 0.39823(7) 0.0393(3) Uani 1 1 d . . . S2 S 1.09190(10) 0.06177(9) 0.12797(7) 0.0368(2) Uani 1 1 d . . . S3 S 0.68401(11) 0.36181(9) 0.16875(8) 0.0412(3) Uani 1 1 d . . . N1 N 0.7848(3) 0.0328(3) 0.2236(2) 0.0329(7) Uani 1 1 d . . . N2 N 0.6658(4) -0.2633(3) 0.2026(2) 0.0382(8) Uani 1 1 d . . . N3 N 0.9730(3) 0.3500(3) 0.2108(2) 0.0320(7) Uani 1 1 d . . . N4 N 1.0932(3) 0.6611(3) 0.1712(2) 0.0377(8) Uani 1 1 d . . . C1 C 0.7052(5) 0.2915(4) 0.4401(3) 0.0451(11) Uani 1 1 d . . . H1 H 0.6939 0.3621 0.3910 0.054 Uiso 1 1 calc R . . C2 C 0.5763(5) 0.2599(5) 0.4608(4) 0.0627(14) Uani 1 1 d . . . H2A H 0.5639 0.2385 0.4051 0.094 Uiso 1 1 calc R . . H2B H 0.4958 0.3320 0.4832 0.094 Uiso 1 1 calc R . . H2C H 0.5871 0.1890 0.5073 0.094 Uiso 1 1 calc R . . C3 C 0.7266(6) 0.3317(5) 0.5250(3) 0.0700(15) Uani 1 1 d . . . H3A H 0.8019 0.3619 0.5074 0.105 Uiso 1 1 calc R . . H3B H 0.7494 0.2604 0.5709 0.105 Uiso 1 1 calc R . . H3C H 0.6421 0.3983 0.5504 0.105 Uiso 1 1 calc R . . C4 C 1.2316(4) 0.0555(4) 0.1838(4) 0.0544(13) Uani 1 1 d . . . H4 H 1.2090 0.1395 0.2029 0.065 Uiso 1 1 calc R . . C5 C 1.2471(6) -0.0417(6) 0.2688(4) 0.0823(17) Uani 1 1 d . . . H5A H 1.1608 -0.0180 0.3134 0.123 Uiso 1 1 calc R . . H5B H 1.3212 -0.0442 0.2963 0.123 Uiso 1 1 calc R . . H5C H 1.2691 -0.1240 0.2503 0.123 Uiso 1 1 calc R . . C6 C 1.3669(5) 0.0189(7) 0.1142(5) 0.111(3) Uani 1 1 d . . . H6A H 1.3567 0.0795 0.0604 0.167 Uiso 1 1 calc R . . H6B H 1.3900 -0.0639 0.0961 0.167 Uiso 1 1 calc R . . H6C H 1.4405 0.0177 0.1415 0.167 Uiso 1 1 calc R . . C7 C 0.5312(4) 0.3189(4) 0.1892(4) 0.0525(12) Uani 1 1 d . . . H7 H 0.5504 0.2380 0.2282 0.063 Uiso 1 1 calc R . . C8 C 0.4052(5) 0.4205(6) 0.2416(4) 0.089(2) Uani 1 1 d . . . H8A H 0.4258 0.4275 0.2992 0.133 Uiso 1 1 calc R . . H8B H 0.3250 0.3974 0.2541 0.133 Uiso 1 1 calc R . . H8C H 0.3856 0.5006 0.2045 0.133 Uiso 1 1 calc R . . C9 C 0.5032(6) 0.3026(6) 0.0993(5) 0.0894(19) Uani 1 1 d . . . H9A H 0.5845 0.2387 0.0679 0.134 Uiso 1 1 calc R . . H9B H 0.4826 0.3816 0.0607 0.134 Uiso 1 1 calc R . . H9C H 0.4247 0.2771 0.1117 0.134 Uiso 1 1 calc R . . C10 C 0.7221(4) -0.0221(4) 0.2978(3) 0.0358(9) Uani 1 1 d . . . H10 H 0.7058 0.0074 0.3553 0.043 Uiso 1 1 calc R . . C11 C 0.6802(4) -0.1188(4) 0.2946(3) 0.0354(9) Uani 1 1 d . . . H11 H 0.6370 -0.1525 0.3488 0.042 Uiso 1 1 calc R . . C12 C 0.7026(4) -0.1668(3) 0.2096(3) 0.0319(9) Uani 1 1 d . . . C13 C 0.7668(4) -0.1073(4) 0.1313(3) 0.0351(9) Uani 1 1 d . . . H13 H 0.7836 -0.1334 0.0725 0.042 Uiso 1 1 calc R . . C14 C 0.8038(4) -0.0123(4) 0.1420(3) 0.0362(9) Uani 1 1 d . . . H14 H 0.8455 0.0248 0.0889 0.043 Uiso 1 1 calc R . . C15 C 0.6068(5) -0.3270(4) 0.2849(3) 0.0501(11) Uani 1 1 d G . . H15A H 0.5996 -0.4006 0.2689 0.075 Uiso 1 1 d G . . H15B H 0.5148 -0.2675 0.3076 0.075 Uiso 1 1 d G . . H15C H 0.6625 -0.3518 0.3322 0.075 Uiso 1 1 d G . . C16 C 0.6875(5) -0.3088(4) 0.1132(3) 0.0481(11) Uani 1 1 d G . . H16A H 0.6544 -0.3772 0.1282 0.072 Uiso 1 1 d G . . H16B H 0.7851 -0.3408 0.0848 0.072 Uiso 1 1 d G . . H16C H 0.6349 -0.2453 0.0708 0.072 Uiso 1 1 d G . . C17 C 1.0306(4) 0.3902(4) 0.1273(3) 0.0362(9) Uani 1 1 d . . . H17 H 1.0433 0.3464 0.0772 0.043 Uiso 1 1 calc R . . C18 C 1.0724(4) 0.4909(4) 0.1099(3) 0.0368(9) Uani 1 1 d . . . H18 H 1.1111 0.5138 0.0497 0.044 Uiso 1 1 calc R . . C19 C 1.0564(4) 0.5600(3) 0.1838(3) 0.0302(9) Uani 1 1 d . . . C20 C 0.9984(4) 0.5155(4) 0.2718(3) 0.0353(9) Uani 1 1 d . . . H20 H 0.9862 0.5553 0.3240 0.042 Uiso 1 1 calc R . . C21 C 0.9599(4) 0.4143(4) 0.2810(3) 0.0368(9) Uani 1 1 d . . . H21 H 0.9219 0.3880 0.3404 0.044 Uiso 1 1 calc R . . C22 C 1.1544(5) 0.7041(4) 0.0794(3) 0.0537(12) Uani 1 1 d G . . H22A H 1.1788 0.7745 0.0824 0.081 Uiso 1 1 d G . . H22B H 1.0868 0.7297 0.0399 0.081 Uiso 1 1 d G . . H22C H 1.2369 0.6352 0.0548 0.081 Uiso 1 1 d G . . C23 C 1.0786(5) 0.7273(4) 0.2493(3) 0.0455(11) Uani 1 1 d G . . H23A H 1.0917 0.8055 0.2264 0.068 Uiso 1 1 d G . . H23B H 1.1432 0.6782 0.2899 0.068 Uiso 1 1 d G . . H23C H 0.9842 0.7453 0.2829 0.068 Uiso 1 1 d G . . C24 C 0.1716(6) 0.1783(6) 0.4645(5) 0.0865(19) Uani 1 1 d . . . H24A H 0.1368 0.1282 0.5164 0.104 Uiso 1 1 calc R . . H24B H 0.1288 0.1832 0.4127 0.104 Uiso 1 1 calc R . . Cl1 Cl 0.12302(19) 0.33184(15) 0.49586(11) 0.0905(5) Uani 1 1 d . . . Cl2 Cl 0.35132(16) 0.10406(16) 0.43380(14) 0.0931(5) 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 0.02721(16) 0.02842(16) 0.03346(16) -0.00432(11) -0.00427(11) -0.01178(12) S1 0.0438(6) 0.0424(6) 0.0346(6) -0.0009(5) -0.0082(5) -0.0199(5) S2 0.0298(5) 0.0358(6) 0.0429(6) -0.0105(5) -0.0018(4) -0.0107(4) S3 0.0352(6) 0.0298(5) 0.0589(7) -0.0007(5) -0.0147(5) -0.0107(5) N1 0.0331(18) 0.0298(17) 0.0359(19) -0.0028(14) -0.0059(15) -0.0125(15) N2 0.045(2) 0.0317(18) 0.043(2) -0.0047(15) -0.0052(16) -0.0212(16) N3 0.0338(18) 0.0324(18) 0.0341(19) -0.0043(15) -0.0067(14) -0.0161(15) N4 0.044(2) 0.0325(18) 0.0388(19) -0.0027(15) -0.0038(16) -0.0189(16) C1 0.050(3) 0.046(3) 0.038(2) -0.009(2) 0.002(2) -0.020(2) C2 0.048(3) 0.069(3) 0.069(3) -0.025(3) 0.003(3) -0.022(3) C3 0.081(4) 0.090(4) 0.053(3) -0.031(3) 0.005(3) -0.046(3) C4 0.035(3) 0.033(2) 0.097(4) -0.010(2) -0.023(3) -0.008(2) C5 0.066(4) 0.102(5) 0.078(4) 0.000(3) -0.033(3) -0.024(3) C6 0.037(3) 0.161(7) 0.115(6) 0.041(5) -0.019(3) -0.036(4) C7 0.032(2) 0.041(3) 0.080(3) 0.005(2) -0.018(2) -0.010(2) C8 0.038(3) 0.098(5) 0.098(5) 0.001(4) -0.004(3) -0.002(3) C9 0.072(4) 0.107(5) 0.115(5) -0.016(4) -0.036(4) -0.047(4) C10 0.034(2) 0.034(2) 0.038(2) -0.0090(18) -0.0012(18) -0.0124(19) C11 0.036(2) 0.032(2) 0.039(2) -0.0026(18) 0.0009(18) -0.0172(18) C12 0.027(2) 0.026(2) 0.040(2) -0.0046(17) -0.0046(17) -0.0075(17) C13 0.037(2) 0.035(2) 0.033(2) -0.0049(18) -0.0068(18) -0.0128(19) C14 0.037(2) 0.040(2) 0.036(2) -0.0001(18) -0.0045(18) -0.0203(19) C15 0.054(3) 0.041(3) 0.058(3) -0.012(2) 0.003(2) -0.025(2) C16 0.056(3) 0.039(2) 0.054(3) -0.010(2) -0.007(2) -0.023(2) C17 0.042(2) 0.035(2) 0.034(2) -0.0083(18) -0.0065(19) -0.0156(19) C18 0.043(2) 0.036(2) 0.032(2) -0.0026(18) -0.0040(18) -0.0172(19) C19 0.025(2) 0.024(2) 0.041(2) -0.0030(17) -0.0088(17) -0.0077(17) C20 0.038(2) 0.035(2) 0.035(2) -0.0068(18) -0.0032(18) -0.0167(19) C21 0.038(2) 0.039(2) 0.033(2) -0.0034(18) -0.0024(18) -0.0170(19) C22 0.068(3) 0.046(3) 0.055(3) 0.000(2) -0.003(2) -0.036(3) C23 0.054(3) 0.037(2) 0.054(3) -0.010(2) -0.007(2) -0.025(2) C24 0.060(4) 0.082(4) 0.122(5) -0.014(4) -0.032(4) -0.023(3) Cl1 0.1059(12) 0.0829(10) 0.0693(9) -0.0247(8) -0.0237(9) -0.0109(9) Cl2 0.0579(9) 0.0851(11) 0.1389(15) -0.0314(10) -0.0121(9) -0.0248(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 In N1 2.373(3) . ? In N3 2.437(3) . ? In S3 2.4428(11) . ? In S1 2.4519(11) . ? In S2 2.4580(11) . ? S1 C1 1.856(4) . ? S2 C4 1.841(4) . ? S3 C7 1.825(4) . ? N1 C10 1.340(5) . ? N1 C14 1.346(5) . ? N2 C12 1.351(5) . ? N2 C16 1.453(5) . ? N2 C15 1.452(5) . ? N3 C17 1.337(5) . ? N3 C21 1.339(5) . ? N4 C19 1.346(5) . ? N4 C23 1.449(5) . ? N4 C22 1.456(5) . ? C1 C2 1.503(6) . ? C1 C3 1.519(6) . ? C4 C6 1.503(7) . ? C4 C5 1.526(7) . ? C7 C9 1.499(7) . ? C7 C8 1.527(7) . ? C10 C11 1.373(5) . ? C11 C12 1.402(5) . ? C12 C13 1.415(5) . ? C13 C14 1.353(5) . ? C17 C18 1.370(5) . ? C18 C19 1.413(5) . ? C19 C20 1.408(5) . ? C20 C21 1.363(5) . ? C24 Cl2 1.725(6) . ? C24 Cl1 1.755(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 In N3 171.59(10) . . ? N1 In S3 93.45(8) . . ? N3 In S3 82.74(8) . . ? N1 In S1 95.61(8) . . ? N3 In S1 92.80(8) . . ? S3 In S1 117.99(4) . . ? N1 In S2 87.80(8) . . ? N3 In S2 87.96(8) . . ? S3 In S2 122.55(4) . . ? S1 In S2 119.01(4) . . ? C1 S1 In 102.44(14) . . ? C4 S2 In 103.11(16) . . ? C7 S3 In 109.82(15) . . ? C10 N1 C14 115.3(3) . . ? C10 N1 In 124.8(3) . . ? C14 N1 In 119.7(2) . . ? C12 N2 C16 121.2(3) . . ? C12 N2 C15 120.8(3) . . ? C16 N2 C15 118.0(3) . . ? C17 N3 C21 115.2(3) . . ? C17 N3 In 121.7(2) . . ? C21 N3 In 122.8(2) . . ? C19 N4 C23 121.0(3) . . ? C19 N4 C22 121.1(3) . . ? C23 N4 C22 117.9(3) . . ? C2 C1 C3 111.8(4) . . ? C2 C1 S1 111.0(3) . . ? C3 C1 S1 108.7(3) . . ? C6 C4 C5 109.5(4) . . ? C6 C4 S2 108.3(4) . . ? C5 C4 S2 110.9(3) . . ? C9 C7 C8 111.6(4) . . ? C9 C7 S3 110.8(4) . . ? C8 C7 S3 109.0(4) . . ? N1 C10 C11 124.4(4) . . ? C10 C11 C12 120.1(4) . . ? N2 C12 C11 122.6(3) . . ? N2 C12 C13 122.0(3) . . ? C11 C12 C13 115.4(3) . . ? C14 C13 C12 119.9(4) . . ? N1 C14 C13 125.1(4) . . ? N3 C17 C18 125.0(4) . . ? C17 C18 C19 119.7(4) . . ? N4 C19 C20 122.3(3) . . ? N4 C19 C18 122.7(3) . . ? C20 C19 C18 115.0(3) . . ? C21 C20 C19 120.3(4) . . ? N3 C21 C20 124.7(4) . . ? Cl2 C24 Cl1 111.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 In S1 C1 -102.27(16) . . . . ? N3 In S1 C1 77.92(16) . . . . ? S3 In S1 C1 -5.34(15) . . . . ? S2 In S1 C1 167.14(14) . . . . ? N1 In S2 C4 -134.15(17) . . . . ? N3 In S2 C4 53.11(17) . . . . ? S3 In S2 C4 133.16(16) . . . . ? S1 In S2 C4 -38.96(16) . . . . ? N1 In S3 C7 22.26(19) . . . . ? N3 In S3 C7 -165.26(19) . . . . ? S1 In S3 C7 -75.95(18) . . . . ? S2 In S3 C7 111.85(18) . . . . ? N3 In N1 C10 -168.4(6) . . . . ? S3 In N1 C10 -105.7(3) . . . . ? S1 In N1 C10 12.9(3) . . . . ? S2 In N1 C10 131.8(3) . . . . ? N3 In N1 C14 16.7(9) . . . . ? S3 In N1 C14 79.3(3) . . . . ? S1 In N1 C14 -162.1(3) . . . . ? S2 In N1 C14 -43.1(3) . . . . ? N1 In N3 C17 -12.6(9) . . . . ? S3 In N3 C17 -76.0(3) . . . . ? S1 In N3 C17 166.2(3) . . . . ? S2 In N3 C17 47.2(3) . . . . ? N1 In N3 C21 160.5(6) . . . . ? S3 In N3 C21 97.1(3) . . . . ? S1 In N3 C21 -20.8(3) . . . . ? S2 In N3 C21 -139.7(3) . . . . ? In S1 C1 C2 90.0(3) . . . . ? In S1 C1 C3 -146.7(3) . . . . ? In S2 C4 C6 -162.1(4) . . . . ? In S2 C4 C5 77.6(4) . . . . ? In S3 C7 C9 -111.5(4) . . . . ? In S3 C7 C8 125.4(3) . . . . ? C14 N1 C10 C11 1.0(6) . . . . ? In N1 C10 C11 -174.2(3) . . . . ? N1 C10 C11 C12 0.1(6) . . . . ? C16 N2 C12 C11 178.6(4) . . . . ? C15 N2 C12 C11 -3.2(6) . . . . ? C16 N2 C12 C13 -1.5(6) . . . . ? C15 N2 C12 C13 176.7(4) . . . . ? C10 C11 C12 N2 178.8(4) . . . . ? C10 C11 C12 C13 -1.1(5) . . . . ? N2 C12 C13 C14 -179.0(4) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C10 N1 C14 C13 -1.1(6) . . . . ? In N1 C14 C13 174.3(3) . . . . ? C12 C13 C14 N1 0.2(6) . . . . ? C21 N3 C17 C18 -1.5(6) . . . . ? In N3 C17 C18 172.1(3) . . . . ? N3 C17 C18 C19 0.5(6) . . . . ? C23 N4 C19 C20 1.9(6) . . . . ? C22 N4 C19 C20 179.3(4) . . . . ? C23 N4 C19 C18 -178.3(4) . . . . ? C22 N4 C19 C18 -0.9(6) . . . . ? C17 C18 C19 N4 -179.0(4) . . . . ? C17 C18 C19 C20 0.8(5) . . . . ? N4 C19 C20 C21 178.7(4) . . . . ? C18 C19 C20 C21 -1.1(5) . . . . ? C17 N3 C21 C20 1.2(6) . . . . ? In N3 C21 C20 -172.3(3) . . . . ? C19 C20 C21 N3 0.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.745 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.062