Supplementary Material (ESI) for Chemical Science This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 #TrackingRef '1316_web_deposit_cif_file_0_MatthiasWeil_1275394739.cif' # start Validation Reply Form _vrf_THETM01_cyclothiophene10 ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The measured crystal diffracted weakly. Although the initial measurement was performed to a theta range up to 26 deg/2Theta, reflections at Theta values greater than 23 deg were too weak. Therefore the data set was cut-off for angles > 23 deg/2 theta. Nevertheless, the refined structure has a data-to-parameter ratio of 11.8 (5618 independent reflections, 3702 observed (2 sigma threshold), 477 parameters) and therefore we believe it is well determined. ; _vrf_PLAT431_cyclothiophene10 ; PROBLEM: Short Inter HL..A Contact Cl6 .. Cl6 .. 2.98 Ang. RESPONSE: This (artificially short) contact originates from a disordered chloroform molecule ; _vrf_PLAT432_cyclothiophene10 ; PROBLEM: Short Inter X...Y Contact CS3 .. Cl9 .. 2.01 Ang. RESPONSE: This (artificially short) contact originates from a disordered chloroform molecule ; _vrf_PLAT023_cyclothiophene10 ; PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 22.99 Deg. RESPONSE: The measured crystal diffracted weakly. Although the initial measurement was performed to a theta range up to 26 deg/2Theta, reflections at Theta values greater than 23 deg were too weak. Therefore the data set was cut-off for angles > 23 deg/2 theta. Nevertheless, the refined structure has a data-to-parameter ratio of 11.8 (5618 independent reflections, 3702 observed (2 sigma threshold), 477 parameters) and therefore we believe it is well determined. ; _vrf_DIFMX01_cyclothiophene10 ; PROMLEM: The maximum difference density is > 0.1*ZMAX*0.75 RESPONSE: The maximum density is caused by a disordered chloroform solvent molecule the disorder of which could be resolved only in parts. ; _vrf_DIFMX02_cyclothiophene10 ; PROMLEM: The maximum difference density is > 0.1*ZMAX*0.75 RESPONSE: The maximum density is caused by a disordered chloroform solvent molecule the disorder of which could be resolved only in parts. ; _vrf_PLAT097_cyclothiophene10 ; PROMLEM: The maximum difference density is > 0.1*ZMAX*0.75 RESPONSE: The maximum density is caused by a disordered chloroform solvent molecule the disorder of which could be resolved only in parts. ; # end Validation Reply Form _publ_section_related_literature ; ; _audit_update_record ; ; _publ_contact_author_name ; Peter B\"auerle ; _publ_contact_author_address ; Institute of Organic Chemistry II and Advanced Materials University of Ulm Albert-Einstein-Allee 11 89081 Ulm Germany ; _publ_contact_author_phone '+43 1 58801 17122' _publ_contact_author_fax '+43 1 58801 17199' _publ_contact_author_email peter.baeuerle@uni-ulm.de _publ_contact_letter ; ; _publ_requested_category ; EM ; _publ_requested_coeditor_name ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_paper_category ? _journal_coeditor_notes ? _journal_techeditor_code ? _iucr_compatibility_tag ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _publ_section_title ; ; loop_ _publ_author_address ; Institute of Organic Chemistry II and Advanced Materials University of Ulm Albert-Einstein-Allee 11 89081 Ulm Germany ; ; Institute of Organic Chemistry II and Advanced Materials University of Ulm Albert-Einstein-Allee 11 89081 Ulm Germany ; ; Institute for Chemical Technologies and Analytics Division of Structural Chemistry Vienna University of Technology Getreidemarkt 9/164-SC A-1060 Vienna Austria ; ; Institute of Inorganic Chemistry University of Stuttgart Pfaffenwaldring 55 D -70569 Stuttgart Germany ; ; Institute of Inorganic Chemistry University of Stuttgart Pfaffenwaldring 55 D -70569 Stuttgart Germany ; ; Institute of Organic Chemistry II and Advanced Materials University of Ulm Albert-Einstein-Allee 11 89081 Ulm Germany ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; All S atoms and most C atoms of the cyclothiophene backbone were localised from structure solution by direct methods. All other C atoms were found during subsequent Fourier syntheses. Two chloroform solvate molecules are heavily disordered around inversion centres. The disorder, which could be resolved only in parts, also causes some artificially short bonds (see alert listing) and high remaining electron density peaks (highest peak 1.6 \%A). H atoms were positioned geometrically (C---H = 0.93 or 0.96 \%A) and refined as riding, with U~iso~(H) = 1.2U~eq~(C) or 1.5U~eq~(methyl C), allowing for free rotation of the methyl groups. ; _publ_section_references ; Bruker (2008). APEX2, SADABS & SAINT. Bruker-AXS Inc. Madison, Wisconsin, USA Sheldrick, G. M. (2008). Acta Crystallogr. A64, 112-122. ; _publ_section_figure_captions ; ; _publ_author_name P.Bauerle data_cyclothiophene[10] _database_code_depnum_ccdc_archive 'CCDC 779279' #TrackingRef '1316_web_deposit_cif_file_0_MatthiasWeil_1275394739.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C72 H84 S10, C3.47 Cl4.19, 2(C H Cl3)' _chemical_formula_sum 'C77.50 H86 Cl10.20 S10' _chemical_formula_weight 1699.65 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' 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 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 11.0629(4) _cell_length_b 13.6610(5) _cell_length_c 15.0564(6) _cell_angle_alpha 93.282(2) _cell_angle_beta 107.469(2) _cell_angle_gamma 106.870(2) _cell_volume 2050.98(13) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3689 _cell_measurement_theta_min 2.325 _cell_measurement_theta_max 23.270 _exptl_crystal_description 'triangular fragment' _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8931 _exptl_absorpt_correction_T_max 0.9504 _exptl_absorpt_process_details ; SADABS (Bruker, 2008) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEXII CCD area detector' _diffrn_measurement_method '\w and \f-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19882 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 22.99 _reflns_number_total 5618 _reflns_number_gt 3702 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material SHELXL-97 _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 'w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+13.4099P] 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 5618 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1242 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.2188 _refine_ls_wR_factor_gt 0.1857 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.34731(18) 0.73598(14) 0.39903(13) 0.0277(5) Uani 1 1 d . . . C1A C 1.4840(7) 0.8443(5) 0.4599(5) 0.0252(17) Uani 1 1 d . . . C1B C 1.5099(7) 0.9117(5) 0.3991(5) 0.0289(18) Uani 1 1 d . . . H1B H 1.5803 0.9739 0.4177 0.035 Uiso 1 1 calc R . . C1C C 1.4211(7) 0.8790(6) 0.3062(5) 0.0288(18) Uani 1 1 d . . . H1C H 1.4274 0.9170 0.2575 0.035 Uiso 1 1 calc R . . C1D C 1.3244(7) 0.7854(6) 0.2945(5) 0.0277(17) Uani 1 1 d . . . S2 S 1.06423(18) 0.65318(14) 0.22258(12) 0.0264(5) Uani 1 1 d . . . C2A C 1.2123(7) 0.7285(5) 0.2103(5) 0.0278(17) Uani 1 1 d . . . C2B C 1.2007(7) 0.7245(6) 0.1177(5) 0.0299(18) Uani 1 1 d . . . H2B H 1.2695 0.7610 0.0970 0.036 Uiso 1 1 calc R . . C2C C 1.0761(7) 0.6607(5) 0.0562(5) 0.0282(18) Uani 1 1 d . . . H2C H 1.0543 0.6508 -0.0091 0.034 Uiso 1 1 calc R . . C2D C 0.9897(7) 0.6145(5) 0.1017(5) 0.0254(17) Uani 1 1 d . . . S3 S 0.81266(18) 0.44832(14) 0.13687(13) 0.0277(5) Uani 1 1 d . . . C3A C 0.8549(7) 0.5388(6) 0.0662(5) 0.0256(17) Uani 1 1 d . . . C3B C 0.7518(7) 0.5281(6) -0.0150(5) 0.0286(18) Uani 1 1 d . . . C3C C 0.6328(7) 0.4427(6) -0.0204(5) 0.0265(17) Uani 1 1 d . . . C3D C 0.6517(7) 0.3959(5) 0.0576(5) 0.0259(17) Uani 1 1 d . . . C31 C 0.7581(8) 0.5976(6) -0.0876(5) 0.0320(18) Uani 1 1 d . . . H31A H 0.8219 0.6651 -0.0569 0.038 Uiso 1 1 calc R . . H31B H 0.6711 0.6063 -0.1138 0.038 Uiso 1 1 calc R . . C32 C 0.7982(9) 0.5591(6) -0.1688(5) 0.039(2) Uani 1 1 d . . . H32A H 0.8798 0.5421 -0.1429 0.047 Uiso 1 1 calc R . . H32B H 0.7284 0.4963 -0.2054 0.047 Uiso 1 1 calc R . . C33 C 0.8204(13) 0.6383(9) -0.2333(7) 0.079(4) Uani 1 1 d . . . H33A H 0.7366 0.6508 -0.2628 0.095 Uiso 1 1 calc R . . H33B H 0.8842 0.7029 -0.1954 0.095 Uiso 1 1 calc R . . C34 C 0.8705(14) 0.6078(10) -0.3085(8) 0.094(4) Uani 1 1 d . . . H34A H 0.9519 0.5927 -0.2803 0.141 Uiso 1 1 calc R . . H34B H 0.8875 0.6637 -0.3437 0.141 Uiso 1 1 calc R . . H34C H 0.8044 0.5475 -0.3500 0.141 Uiso 1 1 calc R . . C35 C 0.5002(7) 0.4186(6) -0.0980(5) 0.0316(18) Uani 1 1 d . . . H35A H 0.4952 0.4821 -0.1223 0.038 Uiso 1 1 calc R . . H35B H 0.4294 0.3966 -0.0708 0.038 Uiso 1 1 calc R . . C36 C 0.4729(7) 0.3357(6) -0.1807(5) 0.0333(19) Uani 1 1 d . . . H36A H 0.5430 0.3563 -0.2088 0.040 Uiso 1 1 calc R . . H36B H 0.4739 0.2708 -0.1581 0.040 Uiso 1 1 calc R . . C37 C 0.3388(8) 0.3207(7) -0.2543(6) 0.047(2) Uani 1 1 d . . . H37A H 0.2700 0.3053 -0.2249 0.056 Uiso 1 1 calc R . . H37B H 0.3404 0.3846 -0.2797 0.056 Uiso 1 1 calc R . . C38 C 0.3048(10) 0.2362(10) -0.3320(8) 0.084(4) Uani 1 1 d . . . H38A H 0.3740 0.2501 -0.3602 0.126 Uiso 1 1 calc R . . H38B H 0.2213 0.2314 -0.3786 0.126 Uiso 1 1 calc R . . H38C H 0.2971 0.1719 -0.3078 0.126 Uiso 1 1 calc R . . S4 S 0.58082(17) 0.32233(14) 0.20717(13) 0.0265(5) Uani 1 1 d . . . C4A C 0.5572(7) 0.3170(6) 0.0873(5) 0.0282(18) Uani 1 1 d . . . C4B C 0.4476(7) 0.2339(6) 0.0378(5) 0.0302(18) Uani 1 1 d . . . H4B H 0.4173 0.2182 -0.0276 0.036 Uiso 1 1 calc R . . C4C C 0.3851(8) 0.1748(6) 0.0942(6) 0.037(2) Uani 1 1 d . . . H4C H 0.3096 0.1164 0.0696 0.045 Uiso 1 1 calc R . . C4D C 0.4460(7) 0.2111(5) 0.1897(5) 0.0273(17) Uani 1 1 d . . . S5 S 0.55511(17) 0.20293(14) 0.37572(13) 0.0275(5) Uani 1 1 d . . . C5A C 0.4194(7) 0.1718(5) 0.2722(5) 0.0266(17) Uani 1 1 d . . . C5B C 0.3025(7) 0.1192(5) 0.2869(5) 0.0258(17) Uani 1 1 d . . . C5C C 0.3216(7) 0.1072(6) 0.3825(5) 0.0298(18) Uani 1 1 d . . . C5D C 0.4532(7) 0.1494(5) 0.4403(5) 0.0274(17) Uani 1 1 d . . . C51 C 0.1688(7) 0.0787(6) 0.2091(5) 0.0318(18) Uani 1 1 d . . . H51A H 0.1672 0.1245 0.1622 0.038 Uiso 1 1 calc R . . H51B H 0.0990 0.0803 0.2352 0.038 Uiso 1 1 calc R . . C52 C 0.1376(8) -0.0315(6) 0.1609(6) 0.041(2) Uani 1 1 d . . . H52A H 0.1936 -0.0297 0.1218 0.049 Uiso 1 1 calc R . . H52B H 0.1615 -0.0734 0.2090 0.049 Uiso 1 1 calc R . . C53 C -0.0075(8) -0.0837(7) 0.1001(7) 0.053(3) Uani 1 1 d . . . H53A H -0.0143 -0.1436 0.0588 0.064 Uiso 1 1 calc R . . H53B H -0.0385 -0.0360 0.0611 0.064 Uiso 1 1 calc R . . C54 C -0.0970(9) -0.1181(8) 0.1611(8) 0.075(4) Uani 1 1 d . . . H54A H -0.0709 -0.1695 0.1960 0.113 Uiso 1 1 calc R . . H54B H -0.1887 -0.1469 0.1212 0.113 Uiso 1 1 calc R . . H54C H -0.0871 -0.0594 0.2041 0.113 Uiso 1 1 calc R . . C55 C 0.2111(7) 0.0577(6) 0.4217(6) 0.0313(18) Uani 1 1 d . . . H55A H 0.1309 0.0723 0.3865 0.038 Uiso 1 1 calc R . . H55B H 0.2374 0.0898 0.4867 0.038 Uiso 1 1 calc R . . C56 C 0.1768(8) -0.0604(6) 0.4184(6) 0.042(2) Uani 1 1 d . . . H56A H 0.2588 -0.0773 0.4427 0.050 Uiso 1 1 calc R . . H56B H 0.1319 -0.0946 0.3536 0.050 Uiso 1 1 calc R . . C57 C 0.0839(8) -0.1009(6) 0.4786(8) 0.059(3) Uani 1 1 d . . . H57A H 0.1273 -0.0637 0.5426 0.071 Uiso 1 1 calc R . . H57B H 0.0008 -0.0861 0.4525 0.071 Uiso 1 1 calc R . . C58 C 0.0526(10) -0.2155(8) 0.4810(8) 0.066(3) Uani 1 1 d . . . H58A H 0.0151 -0.2525 0.4177 0.099 Uiso 1 1 calc R . . H58B H -0.0105 -0.2373 0.5137 0.099 Uiso 1 1 calc R . . H58C H 0.1334 -0.2296 0.5132 0.099 Uiso 1 1 calc R . . C1S C 0.7035(10) 0.1100(7) 0.1503(6) 0.053(2) Uani 1 1 d . . . H1S H 0.6501 0.1569 0.1391 0.064 Uiso 1 1 calc R . . Cl1 Cl 0.7828(3) 0.1157(2) 0.06659(18) 0.0685(8) Uani 1 1 d . . . Cl2 Cl 0.8177(4) 0.1487(4) 0.2627(2) 0.1404(19) Uani 1 1 d . . . Cl3 Cl 0.5957(4) -0.0157(2) 0.1389(4) 0.1281(17) Uani 1 1 d . . . C2S C 0.0000 -0.5000 0.5000 0.16(2) Uani 0.85(8) 2 d SP . . Cl4 Cl -0.032(2) -0.4641(18) 0.6022(11) 0.147(12) Uani 0.242(15) 1 d P . . Cl5 Cl 0.0992(10) -0.4957(9) 0.6035(7) 0.121(6) Uani 0.442(17) 1 d P . . Cl6 Cl 0.1487(10) -0.4606(9) 0.5406(10) 0.138(7) Uani 0.426(18) 1 d P . . CS3 C 0.2628(19) -0.5195(14) 0.5265(14) 0.074(9) Uani 0.60(4) 1 d P . . CS4 C 0.497(2) -0.427(2) 0.5645(15) 0.097(11) Uiso 0.71(6) 1 d P . . Cl7 Cl 0.3588(8) -0.6473(6) 0.4853(5) 0.076(3) Uiso 0.378(10) 1 d P . . Cl8 Cl 0.4902(9) -0.4767(8) 0.6210(8) 0.074(5) Uiso 0.328(13) 1 d P . . Cl9 Cl 0.452(3) -0.514(3) 0.543(2) 0.183(15) Uiso 0.28(2) 1 d P . . 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 S1 0.0238(10) 0.0222(10) 0.0306(11) 0.0002(8) 0.0090(8) -0.0013(8) C1A 0.017(4) 0.018(4) 0.036(5) -0.004(3) 0.011(3) -0.003(3) C1B 0.016(4) 0.019(4) 0.041(5) -0.007(4) 0.008(4) -0.005(3) C1C 0.025(4) 0.027(4) 0.037(5) 0.007(4) 0.017(4) 0.005(4) C1D 0.018(4) 0.027(4) 0.034(4) -0.006(3) 0.009(3) 0.003(3) S2 0.0239(10) 0.0255(11) 0.0246(10) -0.0006(8) 0.0082(8) 0.0010(8) C2A 0.030(4) 0.023(4) 0.035(5) 0.008(3) 0.015(4) 0.009(3) C2B 0.032(4) 0.031(5) 0.031(5) 0.008(4) 0.017(4) 0.010(4) C2C 0.031(4) 0.031(4) 0.023(4) 0.002(3) 0.010(4) 0.010(4) C2D 0.027(4) 0.024(4) 0.023(4) 0.004(3) 0.007(3) 0.008(3) S3 0.0242(10) 0.0270(11) 0.0249(10) 0.0015(8) 0.0039(8) 0.0027(8) C3A 0.029(4) 0.028(4) 0.025(4) 0.001(3) 0.012(4) 0.013(3) C3B 0.034(4) 0.029(4) 0.024(4) -0.004(3) 0.010(4) 0.011(4) C3C 0.026(4) 0.032(4) 0.024(4) -0.003(3) 0.008(3) 0.014(4) C3D 0.019(4) 0.027(4) 0.021(4) -0.009(3) 0.000(3) 0.001(3) C31 0.030(4) 0.037(5) 0.028(4) 0.001(4) 0.008(4) 0.013(4) C32 0.048(5) 0.039(5) 0.031(5) 0.003(4) 0.011(4) 0.019(4) C33 0.153(11) 0.105(9) 0.051(6) 0.057(6) 0.070(7) 0.100(9) C34 0.109(10) 0.094(10) 0.083(9) 0.030(7) 0.038(8) 0.030(8) C35 0.027(4) 0.037(5) 0.031(4) 0.002(4) 0.007(4) 0.013(4) C36 0.033(4) 0.034(5) 0.025(4) -0.004(3) 0.006(4) 0.006(4) C37 0.027(5) 0.068(6) 0.032(5) -0.013(4) 0.003(4) 0.006(4) C38 0.033(6) 0.119(10) 0.077(8) -0.047(7) -0.004(5) 0.022(6) S4 0.0211(10) 0.0231(10) 0.0264(10) -0.0014(8) 0.0023(8) 0.0006(8) C4A 0.024(4) 0.028(4) 0.027(4) 0.000(3) 0.002(3) 0.007(4) C4B 0.019(4) 0.036(5) 0.027(4) -0.004(4) 0.002(3) 0.003(4) C4C 0.030(4) 0.033(5) 0.041(5) -0.005(4) 0.007(4) 0.006(4) C4D 0.018(4) 0.018(4) 0.037(5) -0.002(3) 0.005(3) 0.000(3) S5 0.0163(9) 0.0266(11) 0.0316(11) -0.0008(8) 0.0057(8) -0.0014(8) C5A 0.019(4) 0.023(4) 0.031(4) -0.002(3) 0.003(3) 0.003(3) C5B 0.017(4) 0.018(4) 0.034(4) -0.003(3) 0.002(3) 0.001(3) C5C 0.015(4) 0.025(4) 0.042(5) -0.006(4) 0.009(4) -0.002(3) C5D 0.022(4) 0.023(4) 0.034(5) -0.002(3) 0.012(4) 0.001(3) C51 0.018(4) 0.027(4) 0.042(5) -0.001(4) 0.005(4) 0.001(3) C52 0.028(5) 0.031(5) 0.051(5) -0.004(4) 0.002(4) 0.005(4) C53 0.035(5) 0.028(5) 0.067(7) -0.004(5) -0.015(5) 0.001(4) C54 0.027(5) 0.051(6) 0.101(9) 0.026(6) -0.018(5) -0.016(5) C55 0.019(4) 0.028(4) 0.042(5) -0.004(4) 0.008(4) 0.005(3) C56 0.019(4) 0.032(5) 0.069(6) -0.003(4) 0.017(4) -0.001(4) C57 0.023(5) 0.027(5) 0.126(9) 0.009(5) 0.034(5) -0.002(4) C58 0.053(6) 0.066(7) 0.079(8) 0.018(6) 0.028(6) 0.012(5) C1S 0.075(7) 0.051(6) 0.049(6) 0.012(5) 0.027(5) 0.035(5) Cl1 0.0832(19) 0.0734(18) 0.0616(17) 0.0194(14) 0.0408(15) 0.0249(15) Cl2 0.145(4) 0.248(5) 0.052(2) -0.011(2) 0.006(2) 0.132(4) Cl3 0.163(4) 0.055(2) 0.238(5) 0.047(2) 0.162(4) 0.037(2) C2S 0.13(3) 0.13(3) 0.19(5) 0.07(3) 0.02(3) 0.04(2) Cl4 0.128(18) 0.23(2) 0.051(11) 0.055(12) 0.005(9) 0.037(15) Cl5 0.084(8) 0.166(10) 0.059(6) -0.029(6) 0.003(5) -0.010(6) Cl6 0.068(7) 0.159(11) 0.126(12) 0.003(7) -0.001(6) -0.014(6) CS3 0.073(15) 0.061(13) 0.097(16) 0.026(11) 0.036(12) 0.024(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 S1 C1D 1.726(8) . ? S1 C1A 1.741(7) . ? C1A C1B 1.367(10) . ? C1A C5D 1.438(10) 2_766 ? C1B C1C 1.404(10) . ? C1B H1B 0.9300 . ? C1C C1D 1.370(10) . ? C1C H1C 0.9300 . ? C1D C2A 1.461(10) . ? S2 C2A 1.733(7) . ? S2 C2D 1.735(7) . ? C2A C2B 1.357(10) . ? C2B C2C 1.400(10) . ? C2B H2B 0.9300 . ? C2C C2D 1.370(10) . ? C2C H2C 0.9300 . ? C2D C3A 1.463(10) . ? S3 C3A 1.729(7) . ? S3 C3D 1.730(7) . ? C3A C3B 1.365(10) . ? C3B C3C 1.462(10) . ? C3B C31 1.492(10) . ? C3C C3D 1.359(10) . ? C3C C35 1.507(10) . ? C3D C4A 1.461(10) . ? C31 C32 1.535(10) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.510(11) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.490(14) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.530(10) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.511(10) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.474(12) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? S4 C4D 1.734(7) . ? S4 C4A 1.738(7) . ? C4A C4B 1.370(10) . ? C4B C4C 1.399(10) . ? C4B H4B 0.9300 . ? C4C C4D 1.383(10) . ? C4C H4C 0.9300 . ? C4D C5A 1.456(10) . ? S5 C5A 1.735(7) . ? S5 C5D 1.736(7) . ? C5A C5B 1.374(10) . ? C5B C5C 1.417(10) . ? C5B C51 1.509(10) . ? C5C C5D 1.380(10) . ? C5C C55 1.517(10) . ? C5D C1A 1.438(10) 2_766 ? C51 C52 1.529(10) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 C53 1.517(11) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C54 1.539(14) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 C56 1.540(11) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 C57 1.572(12) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 C58 1.508(12) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C1S Cl2 1.722(10) . ? C1S Cl1 1.732(9) . ? C1S Cl3 1.747(10) . ? C1S H1S 0.9800 . ? C2S Cl6 1.488(10) 2_546 ? C2S Cl6 1.488(10) . ? C2S Cl5 1.601(10) . ? C2S Cl5 1.601(10) 2_546 ? C2S Cl4 1.75(2) 2_546 ? C2S Cl4 1.75(2) . ? Cl4 Cl5 1.63(2) . ? Cl4 Cl6 2.16(2) 2_546 ? Cl4 Cl6 2.43(3) . ? Cl5 Cl6 1.280(13) . ? Cl6 CS3 1.74(2) . ? Cl6 Cl4 2.16(2) 2_546 ? CS3 Cl9 2.01(3) . ? CS4 Cl8 1.13(2) . ? CS4 Cl9 1.14(3) . ? CS4 Cl7 2.00(2) 2_646 ? CS4 Cl9 2.06(4) 2_646 ? Cl7 Cl9 1.82(3) . ? Cl7 CS4 2.00(2) 2_646 ? Cl8 Cl9 1.16(3) . ? Cl9 Cl9 1.89(5) 2_646 ? Cl9 CS4 2.06(4) 2_646 ? 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 C1D S1 C1A 92.5(3) . . ? C1B C1A C5D 131.5(6) . 2_766 ? C1B C1A S1 109.5(5) . . ? C5D C1A S1 119.0(5) 2_766 . ? C1A C1B C1C 114.3(6) . . ? C1A C1B H1B 122.9 . . ? C1C C1B H1B 122.9 . . ? C1D C1C C1B 113.2(7) . . ? C1D C1C H1C 123.4 . . ? C1B C1C H1C 123.4 . . ? C1C C1D C2A 129.4(7) . . ? C1C C1D S1 110.5(6) . . ? C2A C1D S1 120.1(5) . . ? C2A S2 C2D 92.1(3) . . ? C2B C2A C1D 130.5(7) . . ? C2B C2A S2 110.3(6) . . ? C1D C2A S2 119.2(5) . . ? C2A C2B C2C 114.2(7) . . ? C2A C2B H2B 122.9 . . ? C2C C2B H2B 122.9 . . ? C2D C2C C2B 113.2(6) . . ? C2D C2C H2C 123.4 . . ? C2B C2C H2C 123.4 . . ? C2C C2D C3A 131.5(6) . . ? C2C C2D S2 110.2(5) . . ? C3A C2D S2 118.2(5) . . ? C3A S3 C3D 91.4(4) . . ? C3B C3A C2D 130.3(7) . . ? C3B C3A S3 112.4(5) . . ? C2D C3A S3 117.3(5) . . ? C3A C3B C3C 111.6(6) . . ? C3A C3B C31 124.2(7) . . ? C3C C3B C31 124.2(7) . . ? C3D C3C C3B 112.1(6) . . ? C3D C3C C35 124.2(7) . . ? C3B C3C C35 123.3(7) . . ? C3C C3D C4A 130.7(6) . . ? C3C C3D S3 112.4(5) . . ? C4A C3D S3 116.7(5) . . ? C3B C31 C32 114.8(6) . . ? C3B C31 H31A 108.6 . . ? C32 C31 H31A 108.6 . . ? C3B C31 H31B 108.6 . . ? C32 C31 H31B 108.6 . . ? H31A C31 H31B 107.5 . . ? C33 C32 C31 112.6(7) . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? C34 C33 C32 114.5(8) . . ? C34 C33 H33A 108.6 . . ? C32 C33 H33A 108.6 . . ? C34 C33 H33B 108.6 . . ? C32 C33 H33B 108.6 . . ? H33A C33 H33B 107.6 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C3C C35 C36 115.9(6) . . ? C3C C35 H35A 108.3 . . ? C36 C35 H35A 108.3 . . ? C3C C35 H35B 108.3 . . ? C36 C35 H35B 108.3 . . ? H35A C35 H35B 107.4 . . ? C37 C36 C35 110.6(6) . . ? C37 C36 H36A 109.5 . . ? C35 C36 H36A 109.5 . . ? C37 C36 H36B 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 108.1 . . ? C38 C37 C36 112.1(7) . . ? C38 C37 H37A 109.2 . . ? C36 C37 H37A 109.2 . . ? C38 C37 H37B 109.2 . . ? C36 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C4D S4 C4A 93.0(4) . . ? C4B C4A C3D 132.2(7) . . ? C4B C4A S4 109.6(5) . . ? C3D C4A S4 118.2(5) . . ? C4A C4B C4C 114.2(7) . . ? C4A C4B H4B 122.9 . . ? C4C C4B H4B 122.9 . . ? C4D C4C C4B 113.8(7) . . ? C4D C4C H4C 123.1 . . ? C4B C4C H4C 123.1 . . ? C4C C4D C5A 132.3(7) . . ? C4C C4D S4 109.3(6) . . ? C5A C4D S4 118.4(5) . . ? C5A S5 C5D 91.9(3) . . ? C5B C5A C4D 131.9(7) . . ? C5B C5A S5 111.3(5) . . ? C4D C5A S5 116.6(5) . . ? C5A C5B C5C 112.7(6) . . ? C5A C5B C51 123.3(7) . . ? C5C C5B C51 124.0(6) . . ? C5D C5C C5B 113.4(6) . . ? C5D C5C C55 121.4(7) . . ? C5B C5C C55 125.2(6) . . ? C5C C5D C1A 131.8(6) . 2_766 ? C5C C5D S5 110.6(5) . . ? C1A C5D S5 117.5(5) 2_766 . ? C5B C51 C52 113.6(6) . . ? C5B C51 H51A 108.8 . . ? C52 C51 H51A 108.8 . . ? C5B C51 H51B 108.8 . . ? C52 C51 H51B 108.8 . . ? H51A C51 H51B 107.7 . . ? C53 C52 C51 114.6(7) . . ? C53 C52 H52A 108.6 . . ? C51 C52 H52A 108.6 . . ? C53 C52 H52B 108.6 . . ? C51 C52 H52B 108.6 . . ? H52A C52 H52B 107.6 . . ? C52 C53 C54 111.2(8) . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C5C C55 C56 114.8(6) . . ? C5C C55 H55A 108.6 . . ? C56 C55 H55A 108.6 . . ? C5C C55 H55B 108.6 . . ? C56 C55 H55B 108.6 . . ? H55A C55 H55B 107.5 . . ? C55 C56 C57 110.9(6) . . ? C55 C56 H56A 109.5 . . ? C57 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? C57 C56 H56B 109.5 . . ? H56A C56 H56B 108.0 . . ? C58 C57 C56 112.8(7) . . ? C58 C57 H57A 109.0 . . ? C56 C57 H57A 109.0 . . ? C58 C57 H57B 109.0 . . ? C56 C57 H57B 109.0 . . ? H57A C57 H57B 107.8 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? Cl2 C1S Cl1 111.3(6) . . ? Cl2 C1S Cl3 110.5(5) . . ? Cl1 C1S Cl3 109.8(5) . . ? Cl2 C1S H1S 108.4 . . ? Cl1 C1S H1S 108.4 . . ? Cl3 C1S H1S 108.4 . . ? Cl6 C2S Cl6 180.000(2) 2_546 . ? Cl6 C2S Cl5 131.2(5) 2_546 . ? Cl6 C2S Cl5 48.8(5) . . ? Cl6 C2S Cl5 48.8(5) 2_546 2_546 ? Cl6 C2S Cl5 131.2(5) . 2_546 ? Cl5 C2S Cl5 180.0(9) . 2_546 ? Cl6 C2S Cl4 97.0(9) 2_546 2_546 ? Cl6 C2S Cl4 83.0(9) . 2_546 ? Cl5 C2S Cl4 122.3(7) . 2_546 ? Cl5 C2S Cl4 57.7(7) 2_546 2_546 ? Cl6 C2S Cl4 83.0(9) 2_546 . ? Cl6 C2S Cl4 97.0(9) . . ? Cl5 C2S Cl4 57.7(7) . . ? Cl5 C2S Cl4 122.3(7) 2_546 . ? Cl4 C2S Cl4 180.0(12) 2_546 . ? Cl5 Cl4 C2S 56.4(8) . . ? Cl5 Cl4 Cl6 95.0(12) . 2_546 ? C2S Cl4 Cl6 43.2(5) . 2_546 ? Cl5 Cl4 Cl6 28.9(6) . . ? C2S Cl4 Cl6 37.4(5) . . ? Cl6 Cl4 Cl6 80.5(8) 2_546 . ? Cl6 Cl5 C2S 61.0(6) . . ? Cl6 Cl5 Cl4 113.2(12) . . ? C2S Cl5 Cl4 65.9(7) . . ? Cl5 Cl6 C2S 70.2(7) . . ? Cl5 Cl6 CS3 111.5(12) . . ? C2S Cl6 CS3 128.5(10) . . ? Cl5 Cl6 Cl4 115.1(8) . 2_546 ? C2S Cl6 Cl4 53.8(7) . 2_546 ? CS3 Cl6 Cl4 84.7(11) . 2_546 ? Cl5 Cl6 Cl4 37.9(8) . . ? C2S Cl6 Cl4 45.7(6) . . ? CS3 Cl6 Cl4 147.6(11) . . ? Cl4 Cl6 Cl4 99.5(8) 2_546 . ? Cl6 CS3 Cl9 150.7(15) . . ? Cl8 CS4 Cl9 61.4(18) . . ? Cl8 CS4 Cl7 135.4(16) . 2_646 ? Cl9 CS4 Cl7 117.1(19) . 2_646 ? Cl8 CS4 Cl9 115(2) . 2_646 ? Cl9 CS4 Cl9 65(2) . 2_646 ? Cl7 CS4 Cl9 53.3(10) 2_646 2_646 ? Cl9 Cl7 CS4 65.0(11) . 2_646 ? CS4 Cl8 Cl9 59.7(14) . . ? CS4 Cl9 Cl8 58.9(19) . . ? CS4 Cl9 Cl7 168(2) . . ? Cl8 Cl9 Cl7 131(2) . . ? CS4 Cl9 Cl9 82(2) . 2_646 ? Cl8 Cl9 Cl9 126(3) . 2_646 ? Cl7 Cl9 Cl9 94(2) . 2_646 ? CS4 Cl9 CS3 95(2) . . ? Cl8 Cl9 CS3 92.6(16) . . ? Cl7 Cl9 CS3 78.5(12) . . ? Cl9 Cl9 CS3 129(2) 2_646 . ? CS4 Cl9 CS4 115(2) . 2_646 ? Cl8 Cl9 CS4 145.1(19) . 2_646 ? Cl7 Cl9 CS4 61.7(15) . 2_646 ? Cl9 Cl9 CS4 33.1(12) 2_646 2_646 ? CS3 Cl9 CS4 122.1(18) . 2_646 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 22.99 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.693 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.102