# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Fourmigue, Marc' _publ_contact_author_name 'Fourmigue, Marc' _publ_contact_author_email marc.fourmigue@univ-rennes1.fr _publ_section_title ; Combining Halogen Bonding and Chirality in a Two-Dimensional Organic Metal (EDT-TTF-I2)2(D\^aCamphorsulfonate)\^a\/cH2O ; # Attachment 'MB45-2.cif.txt' data_MB45 _database_code_depnum_ccdc_archive 'CCDC 768025' #TrackingRef 'MB45-2.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration syn _chemical_formula_moiety ' C10 H15 O4 S, 2(C8 H4 I2 S6), O ' _chemical_formula_sum 'C26 H23 I4 O5 S13' _chemical_formula_weight 1339.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 _symmetry_space_group_name_Hall ' P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.6737(2) _cell_length_b 8.1634(2) _cell_length_c 17.7545(6) _cell_angle_alpha 79.5930(19) _cell_angle_beta 87.517(2) _cell_angle_gamma 65.233(2) _cell_volume 992.64(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3461 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 639 _exptl_absorpt_coefficient_mu 3.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.481 _exptl_absorpt_correction_T_max 0.824 #----------------------------- Remark ------------------------------# # Tmax and Tmin values correspond to EXPECTED values calculated # # from crystal size. In the case of absorption correction performed # # with SADABS program, Tmax should be given as Tmax_expected and # # and Tmin = Tmax * 'relative-correction-factor'. # # SADABS output: # # Ratio of minimum to maximum apparent transmission: 0.660633 #-------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12066 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7679 _reflns_number_gt 6453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0188P)^2^+1.2625P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 7679 _refine_ls_number_parameters 447 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.023 _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 I1 I 0.84174(8) 0.77891(7) 0.59856(3) 0.04620(18) Uani 1 1 d . . . I2 I 0.32288(7) 1.03602(6) 0.52834(3) 0.03921(16) Uani 1 1 d . . . S1 S 0.6551(4) 0.6375(4) 0.75032(15) 0.0384(6) Uani 1 1 d . . . S2 S 0.2531(4) 0.8328(4) 0.69581(13) 0.0371(6) Uani 1 1 d . . . S3 S 0.5236(4) 0.4507(4) 0.90543(13) 0.0384(6) Uani 1 1 d . . . S4 S 0.1229(4) 0.6378(4) 0.84950(15) 0.0397(6) Uani 1 1 d . . . S5 S 0.4466(5) 0.2619(4) 1.05222(15) 0.0477(7) Uani 1 1 d . . . S6 S -0.0327(5) 0.4875(4) 0.98502(17) 0.0468(7) Uani 1 1 d . . . C1 C 0.2390(19) 0.2570(13) 1.1016(6) 0.036(3) Uani 0.714(19) 1 d PD A 1 H1A H 0.2130 0.1589 1.0885 0.044 Uiso 0.714(19) 1 calc PR A 1 H1B H 0.2666 0.2301 1.1564 0.044 Uiso 0.714(19) 1 calc PR A 1 C2 C 0.062(2) 0.4355(18) 1.0824(7) 0.043(3) Uani 0.714(19) 1 d PD A 1 H2A H 0.0927 0.5346 1.0910 0.051 Uiso 0.714(19) 1 calc PR A 1 H2B H -0.0374 0.4312 1.1173 0.051 Uiso 0.714(19) 1 calc PR A 1 C1C C 0.222(4) 0.387(4) 1.1035(14) 0.049(6) Uani 0.286(19) 1 d PD A 2 H1C1 H 0.2452 0.3436 1.1583 0.059 Uiso 0.286(19) 1 calc PR A 2 H1C2 H 0.1918 0.5171 1.0937 0.059 Uiso 0.286(19) 1 calc PR A 2 C2C C 0.050(4) 0.361(4) 1.0786(15) 0.049(6) Uani 0.286(19) 1 d PD A 2 H2C1 H -0.0524 0.4014 1.1142 0.059 Uiso 0.286(19) 1 calc PR A 2 H2C2 H 0.0860 0.2314 1.0789 0.059 Uiso 0.286(19) 1 calc PR A 2 C3 C 0.1665(15) 0.4958(14) 0.9386(5) 0.038(2) Uani 1 1 d . A . C4 C 0.3529(14) 0.4114(12) 0.9628(5) 0.037(2) Uani 1 1 d . A . C5 C 0.3588(13) 0.5965(11) 0.8320(5) 0.0276(18) Uani 1 1 d . . . C6 C 0.4127(14) 0.6807(14) 0.7660(5) 0.035(2) Uani 1 1 d . . . C7 C 0.4191(14) 0.8648(13) 0.6345(5) 0.035(2) Uani 1 1 d . . . C8 C 0.6052(14) 0.7780(13) 0.6579(5) 0.031(2) Uani 1 1 d . . . I3 I 0.45945(7) -0.26374(6) 1.07448(3) 0.04089(16) Uani 1 1 d . . . I4 I -0.05947(8) -0.00877(7) 0.99812(3) 0.04685(18) Uani 1 1 d . . . S7 S 0.8316(5) 0.2765(4) 0.61935(17) 0.0463(7) Uani 1 1 d . . . S8 S 0.6742(4) 0.1205(4) 0.75508(14) 0.0416(6) Uani 1 1 d . . . S9 S 0.2715(4) 0.3149(4) 0.69678(14) 0.0393(6) Uani 1 1 d . . . S10 S 0.3544(5) 0.5071(4) 0.55409(16) 0.0470(7) Uani 1 1 d . . . S11 S 0.5377(4) -0.0725(4) 0.90725(13) 0.0385(6) Uani 1 1 d . . . S12 S 0.1359(4) 0.1264(4) 0.84969(14) 0.0371(6) Uani 1 1 d . . . C9 C 0.7461(19) 0.3235(17) 0.5197(6) 0.066(3) Uani 1 1 d . . . H9A H 0.8430 0.3399 0.4862 0.079 Uiso 1 1 calc R . . H9B H 0.7300 0.2180 0.5092 0.079 Uiso 1 1 calc R . . C10 C 0.563(2) 0.487(2) 0.5017(7) 0.099(5) Uani 1 1 d . . . H10A H 0.5302 0.4999 0.4482 0.119 Uiso 1 1 calc R . . H10B H 0.5876 0.5925 0.5061 0.119 Uiso 1 1 calc R . . C11 C 0.4452(14) 0.3595(13) 0.6385(5) 0.034(2) Uani 1 1 d . . . C12 C 0.6276(14) 0.2685(11) 0.6660(5) 0.033(2) Uani 1 1 d . . . C13 C 0.4311(14) 0.1620(14) 0.7699(5) 0.039(2) Uani 1 1 d . . . C14 C 0.3729(13) 0.0867(12) 0.8339(5) 0.032(2) Uani 1 1 d . . . C15 C 0.1781(14) -0.0012(14) 0.9391(5) 0.035(2) Uani 1 1 d . . . C16 C 0.3594(13) -0.0969(12) 0.9680(5) 0.0292(19) Uani 1 1 d . . . C1A C 0.9506(16) 0.9250(14) 0.3885(5) 0.068(3) Uani 1 1 d . B . C2A C 0.822(2) 1.1092(19) 0.3441(6) 0.132(5) Uani 1 1 d . . . H2A1 H 0.6953 1.1562 0.3650 0.158 Uiso 1 1 calc R . . H2A2 H 0.8767 1.1975 0.3426 0.158 Uiso 1 1 calc R . . C3A C 0.818(2) 1.0647(15) 0.2703(8) 0.111(5) Uani 1 1 d . . . H3A H 0.7131 1.1615 0.2369 0.134 Uiso 1 1 calc R . . C4A C 1.0156(16) 1.0217(14) 0.2345(5) 0.088(3) Uani 1 1 d . . . H4A1 H 1.0662 1.1079 0.2430 0.106 Uiso 1 1 calc R . . H4A2 H 1.0089 1.0231 0.1799 0.106 Uiso 1 1 calc R . . C5A C 1.1380(17) 0.8256(15) 0.2789(9) 0.124(6) Uani 1 1 d . B . H5A1 H 1.1945 0.7392 0.2442 0.149 Uiso 1 1 calc R . . H5A2 H 1.2390 0.8240 0.3104 0.149 Uiso 1 1 calc R . . C6A C 0.9856(17) 0.7831(17) 0.3286(6) 0.078(3) Uani 1 1 d . . . C7A C 0.8062(17) 0.8884(16) 0.2798(5) 0.087(3) Uani 1 1 d . B . C8A C 0.640(2) 0.864(3) 0.3349(7) 0.143(5) Uani 1 1 d . . . H8A1 H 0.5172 0.9321 0.3087 0.215 Uiso 1 1 calc R B . H8A2 H 0.6406 0.9093 0.3812 0.215 Uiso 1 1 calc R . . H8A3 H 0.6652 0.7367 0.3473 0.215 Uiso 1 1 calc R . . C9A C 0.788(3) 0.841(3) 0.2060(9) 0.143(5) Uani 1 1 d . . . H9A1 H 0.6658 0.9249 0.1818 0.215 Uiso 1 1 calc R B . H9A2 H 0.7962 0.7184 0.2139 0.215 Uiso 1 1 calc R . . H9A3 H 0.8890 0.8487 0.1740 0.215 Uiso 1 1 calc R . . O4 O 1.0138(12) 0.8734(12) 0.4514(4) 0.112(3) Uani 1 1 d . . . C10A C 1.0439(18) 0.5945(15) 0.3715(6) 0.100(3) Uani 0.577(12) 1 d PD B 1 H10C H 0.9270 0.5767 0.3807 0.120 Uiso 0.577(12) 1 calc PR B 1 H10D H 1.0940 0.5917 0.4211 0.120 Uiso 0.577(12) 1 calc PR B 1 S13A S 1.2185(13) 0.3889(8) 0.3359(4) 0.100(3) Uani 0.577(12) 1 d PD B 1 O1A O 1.218(3) 0.231(2) 0.3849(9) 0.094(5) Uiso 0.577(12) 1 d PD B 1 O2A O 1.154(4) 0.410(3) 0.2591(9) 0.199(10) Uiso 0.577(12) 1 d PD B 1 O3A O 1.3874(16) 0.4175(17) 0.3438(7) 0.096(4) Uiso 0.577(12) 1 d PD B 1 C10B C 1.0439(18) 0.5945(15) 0.3715(6) 0.100(3) Uani 0.423(12) 1 d PD B 2 H10E H 0.9325 0.5905 0.3983 0.120 Uiso 0.423(12) 1 calc PR B 2 H10F H 1.1390 0.5750 0.4104 0.120 Uiso 0.423(12) 1 calc PR B 2 S13B S 1.1404(12) 0.3995(9) 0.3232(4) 0.0594(19) Uani 0.423(12) 1 d PD B 2 O1B O 0.988(2) 0.415(2) 0.2749(8) 0.093(5) Uiso 0.423(12) 1 d PD B 2 O2B O 1.285(3) 0.402(3) 0.2697(12) 0.123(8) Uiso 0.423(12) 1 d PD B 2 O3B O 1.143(4) 0.286(3) 0.3955(9) 0.095(7) Uiso 0.423(12) 1 d PD B 2 O5 O 0.5891(15) 0.5133(12) 0.2190(5) 0.105(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 I1 0.0354(4) 0.0523(4) 0.0534(4) -0.0078(3) 0.0130(3) -0.0225(3) I2 0.0384(4) 0.0439(4) 0.0302(3) -0.0013(2) 0.0010(3) -0.0143(3) S1 0.0270(14) 0.0487(15) 0.0372(12) -0.0051(10) 0.0033(10) -0.0147(12) S2 0.0253(13) 0.0513(14) 0.0312(11) -0.0012(10) 0.0000(10) -0.0149(11) S3 0.0310(13) 0.0471(15) 0.0298(11) 0.0018(10) -0.0001(10) -0.0127(12) S4 0.0293(13) 0.0507(14) 0.0358(11) 0.0005(9) -0.0012(10) -0.0165(11) S5 0.0493(15) 0.0479(15) 0.0355(12) 0.0083(11) -0.0010(11) -0.0164(12) S6 0.0384(15) 0.0526(16) 0.0490(15) -0.0025(12) 0.0101(12) -0.0219(12) C1 0.051(7) 0.026(5) 0.038(6) -0.007(4) 0.000(5) -0.021(5) C2 0.048(8) 0.044(7) 0.040(7) -0.016(6) 0.030(6) -0.024(7) C1C 0.073(16) 0.049(13) 0.040(9) -0.010(8) 0.018(8) -0.040(11) C2C 0.073(16) 0.049(13) 0.040(9) -0.010(8) 0.018(8) -0.040(11) C3 0.040(5) 0.055(6) 0.026(4) -0.008(4) 0.010(4) -0.028(5) C4 0.030(5) 0.029(5) 0.046(5) -0.012(4) 0.001(4) -0.006(4) C5 0.027(4) 0.030(4) 0.032(4) -0.007(3) 0.002(3) -0.017(4) C6 0.029(5) 0.053(6) 0.030(4) -0.011(4) 0.004(4) -0.023(5) C7 0.038(5) 0.039(5) 0.029(4) -0.002(4) -0.006(4) -0.017(5) C8 0.033(5) 0.041(5) 0.026(4) -0.005(3) 0.002(3) -0.024(4) I3 0.0417(4) 0.0412(4) 0.0343(3) -0.0003(3) 0.0003(3) -0.0146(3) I4 0.0324(4) 0.0501(4) 0.0578(4) -0.0042(3) 0.0112(3) -0.0201(3) S7 0.0337(13) 0.0573(16) 0.0486(15) -0.0007(12) 0.0074(12) -0.0238(12) S8 0.0282(13) 0.0583(15) 0.0318(11) 0.0042(10) -0.0003(9) -0.0166(11) S9 0.0257(13) 0.0534(16) 0.0358(12) -0.0006(10) -0.0013(10) -0.0164(12) S10 0.0434(14) 0.0439(14) 0.0399(13) 0.0070(11) -0.0004(11) -0.0104(12) S11 0.0282(13) 0.0543(15) 0.0298(11) 0.0009(10) -0.0019(10) -0.0173(12) S12 0.0251(13) 0.0499(15) 0.0312(11) 0.0015(10) -0.0046(10) -0.0138(12) C9 0.063(7) 0.068(7) 0.042(5) -0.003(5) 0.003(5) -0.006(6) C10 0.060(8) 0.141(12) 0.057(7) 0.022(7) 0.024(6) -0.021(8) C11 0.044(5) 0.043(5) 0.020(3) 0.002(3) 0.003(3) -0.026(4) C12 0.032(5) 0.023(4) 0.043(5) -0.006(3) 0.000(4) -0.009(4) C13 0.030(5) 0.051(6) 0.028(4) -0.004(4) -0.004(4) -0.010(4) C14 0.028(5) 0.033(5) 0.033(4) -0.002(4) -0.005(4) -0.011(4) C15 0.029(5) 0.041(5) 0.033(4) -0.008(3) 0.004(4) -0.013(4) C16 0.025(4) 0.040(5) 0.026(4) -0.010(3) 0.009(3) -0.016(4) C1A 0.086(7) 0.079(5) 0.037(4) 0.010(4) -0.003(4) -0.041(5) C2A 0.170(13) 0.176(13) 0.059(6) -0.042(7) 0.049(7) -0.078(11) C3A 0.135(12) 0.054(7) 0.108(9) -0.014(6) -0.025(8) -0.002(7) C4A 0.120(8) 0.124(8) 0.044(4) 0.012(4) 0.002(5) -0.084(7) C5A 0.073(7) 0.089(7) 0.181(13) 0.006(8) 0.064(8) -0.023(6) C6A 0.080(7) 0.080(8) 0.057(5) -0.004(6) 0.020(5) -0.023(7) C7A 0.087(7) 0.093(7) 0.054(5) -0.021(5) -0.020(5) -0.008(6) C8A 0.120(8) 0.264(15) 0.072(6) -0.022(7) 0.006(6) -0.108(10) C9A 0.120(8) 0.264(15) 0.072(6) -0.022(7) 0.006(6) -0.108(10) O4 0.149(7) 0.179(7) 0.048(3) -0.021(4) 0.004(4) -0.108(6) C10A 0.122(9) 0.098(7) 0.070(6) -0.006(5) -0.004(6) -0.040(7) S13A 0.187(8) 0.063(3) 0.053(3) 0.008(2) -0.041(4) -0.060(4) C10B 0.122(9) 0.098(7) 0.070(6) -0.006(5) -0.004(6) -0.040(7) S13B 0.086(4) 0.052(3) 0.038(3) 0.005(2) -0.012(3) -0.032(3) O5 0.122(8) 0.080(5) 0.061(4) 0.045(4) -0.015(4) -0.014(5) _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 I1 C8 2.061(9) . ? I2 C7 2.087(9) . ? S1 C6 1.761(10) . ? S1 C8 1.778(9) . ? S2 C6 1.701(10) . ? S2 C7 1.713(10) . ? S3 C4 1.724(10) . ? S3 C5 1.742(9) . ? S4 C5 1.722(9) . ? S4 C3 1.736(10) . ? S5 C4 1.787(10) . ? S5 C1 1.797(13) . ? S5 C1C 1.89(3) . ? S6 C3 1.726(10) . ? S6 C2C 1.78(3) . ? S6 C2 1.811(15) . ? C1 C2 1.512(16) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1C C2C 1.518(17) . ? C1C H1C1 0.9700 . ? C1C H1C2 0.9700 . ? C2C H2C1 0.9700 . ? C2C H2C2 0.9700 . ? C3 C4 1.352(14) . ? C5 C6 1.387(11) . ? C7 C8 1.346(14) . ? I3 C16 2.082(9) . ? I4 C15 2.081(10) . ? S7 C12 1.759(10) . ? S7 C9 1.830(12) . ? S8 C12 1.757(9) . ? S8 C13 1.767(10) . ? S9 C13 1.737(9) . ? S9 C11 1.770(9) . ? S10 C11 1.708(8) . ? S10 C10 1.778(12) . ? S11 C16 1.760(9) . ? S11 C14 1.771(9) . ? S12 C15 1.695(9) . ? S12 C14 1.728(10) . ? C9 C10 1.475(17) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.344(14) . ? C13 C14 1.342(12) . ? C15 C16 1.348(14) . ? C1A O4 1.168(11) . ? C1A C2A 1.500(16) . ? C1A C6A 1.644(16) . ? C2A C3A 1.427(17) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C7A 1.457(15) . ? C3A C4A 1.544(18) . ? C3A H3A 0.9800 . ? C4A C5A 1.554(14) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.552(14) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A C10A 1.476(14) . ? C6A C7A 1.492(14) . ? C7A C9A 1.460(17) . ? C7A C8A 1.628(18) . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? C10A S13A 1.854(12) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? S13A O1A 1.419(9) . ? S13A O2A 1.425(9) . ? S13A O3A 1.427(9) . ? S13B O1B 1.427(9) . ? S13B O2B 1.434(9) . ? S13B O3B 1.436(9) . ? 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 C6 S1 C8 93.8(4) . . ? C6 S2 C7 96.6(5) . . ? C4 S3 C5 94.2(4) . . ? C5 S4 C3 96.4(5) . . ? C4 S5 C1 104.7(5) . . ? C4 S5 C1C 92.6(9) . . ? C3 S6 C2C 106.2(9) . . ? C3 S6 C2 97.8(6) . . ? C2 C1 S5 113.0(8) . . ? C2 C1 H1A 109.0 . . ? S5 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? S5 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C1 C2 S6 114.7(8) . . ? C1 C2 H2A 108.6 . . ? S6 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? S6 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2C C1C S5 112.7(19) . . ? C2C C1C H1C1 109.1 . . ? S5 C1C H1C1 109.1 . . ? C2C C1C H1C2 109.1 . . ? S5 C1C H1C2 109.1 . . ? H1C1 C1C H1C2 107.8 . . ? C1C C2C S6 109.9(18) . . ? C1C C2C H2C1 109.7 . . ? S6 C2C H2C1 109.7 . . ? C1C C2C H2C2 109.7 . . ? S6 C2C H2C2 109.7 . . ? H2C1 C2C H2C2 108.2 . . ? C4 C3 S6 129.1(8) . . ? C4 C3 S4 114.7(7) . . ? S6 C3 S4 116.1(6) . . ? C3 C4 S3 119.4(7) . . ? C3 C4 S5 126.3(8) . . ? S3 C4 S5 114.3(5) . . ? C6 C5 S4 122.4(7) . . ? C6 C5 S3 122.3(7) . . ? S4 C5 S3 115.2(5) . . ? C5 C6 S2 123.2(7) . . ? C5 C6 S1 121.3(7) . . ? S2 C6 S1 115.5(5) . . ? C8 C7 S2 117.8(7) . . ? C8 C7 I2 123.7(7) . . ? S2 C7 I2 118.6(5) . . ? C7 C8 S1 116.2(7) . . ? C7 C8 I1 128.2(7) . . ? S1 C8 I1 115.6(5) . . ? C12 S7 C9 99.3(6) . . ? C12 S8 C13 94.7(5) . . ? C13 S9 C11 96.3(5) . . ? C11 S10 C10 103.4(6) . . ? C16 S11 C14 94.7(5) . . ? C15 S12 C14 95.4(4) . . ? C10 C9 S7 113.5(9) . . ? C10 C9 H9A 108.9 . . ? S7 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? S7 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 S10 121.1(10) . . ? C9 C10 H10A 107.0 . . ? S10 C10 H10A 107.0 . . ? C9 C10 H10B 107.0 . . ? S10 C10 H10B 107.0 . . ? H10A C10 H10B 106.8 . . ? C12 C11 S10 130.0(8) . . ? C12 C11 S9 115.6(7) . . ? S10 C11 S9 114.4(6) . . ? C11 C12 S8 118.7(7) . . ? C11 C12 S7 126.0(7) . . ? S8 C12 S7 115.3(6) . . ? C14 C13 S9 122.4(7) . . ? C14 C13 S8 122.8(7) . . ? S9 C13 S8 114.8(5) . . ? C13 C14 S12 123.5(7) . . ? C13 C14 S11 121.9(7) . . ? S12 C14 S11 114.5(5) . . ? C16 C15 S12 120.2(8) . . ? C16 C15 I4 122.8(7) . . ? S12 C15 I4 117.0(5) . . ? C15 C16 S11 114.9(7) . . ? C15 C16 I3 129.8(7) . . ? S11 C16 I3 115.3(5) . . ? O4 C1A C2A 133.8(11) . . ? O4 C1A C6A 121.8(9) . . ? C2A C1A C6A 104.3(8) . . ? C3A C2A C1A 100.8(10) . . ? C3A C2A H2A1 111.6 . . ? C1A C2A H2A1 111.6 . . ? C3A C2A H2A2 111.6 . . ? C1A C2A H2A2 111.6 . . ? H2A1 C2A H2A2 109.4 . . ? C2A C3A C7A 108.9(12) . . ? C2A C3A C4A 109.1(13) . . ? C7A C3A C4A 102.1(10) . . ? C2A C3A H3A 112.1 . . ? C7A C3A H3A 112.1 . . ? C4A C3A H3A 112.1 . . ? C3A C4A C5A 101.8(7) . . ? C3A C4A H4A1 111.4 . . ? C5A C4A H4A1 111.4 . . ? C3A C4A H4A2 111.4 . . ? C5A C4A H4A2 111.4 . . ? H4A1 C4A H4A2 109.3 . . ? C6A C5A C4A 101.8(9) . . ? C6A C5A H5A1 111.4 . . ? C4A C5A H5A1 111.4 . . ? C6A C5A H5A2 111.4 . . ? C4A C5A H5A2 111.4 . . ? H5A1 C5A H5A2 109.3 . . ? C10A C6A C7A 124.6(13) . . ? C10A C6A C5A 117.5(9) . . ? C7A C6A C5A 102.7(10) . . ? C10A C6A C1A 110.0(8) . . ? C7A C6A C1A 99.1(9) . . ? C5A C6A C1A 98.5(10) . . ? C3A C7A C9A 111.5(12) . . ? C3A C7A C6A 95.8(12) . . ? C9A C7A C6A 120.6(11) . . ? C3A C7A C8A 116.7(12) . . ? C9A C7A C8A 108.7(12) . . ? C6A C7A C8A 103.4(9) . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C7A C9A H9A1 109.5 . . ? C7A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C7A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C6A C10A S13A 123.3(8) . . ? C6A C10A H10C 106.5 . . ? S13A C10A H10C 106.5 . . ? C6A C10A H10D 106.5 . . ? S13A C10A H10D 106.5 . . ? H10C C10A H10D 106.5 . . ? O1A S13A O2A 113.8(14) . . ? O1A S13A O3A 114.2(10) . . ? O2A S13A O3A 115.5(13) . . ? O1A S13A C10A 108.1(10) . . ? O2A S13A C10A 104.9(11) . . ? O3A S13A C10A 98.2(7) . . ? O1B S13B O2B 102.6(12) . . ? O1B S13B O3B 109.3(13) . . ? O2B S13B O3B 133.7(15) . . ? 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 C4 S5 C1 C2 -31.9(10) . . . . ? C1C S5 C1 C2 38.7(16) . . . . ? S5 C1 C2 S6 68.3(12) . . . . ? C3 S6 C2 C1 -60.9(11) . . . . ? C2C S6 C2 C1 54(3) . . . . ? C4 S5 C1C C2C 69(2) . . . . ? C1 S5 C1C C2C -44.9(16) . . . . ? S5 C1C C2C S6 -73(3) . . . . ? C3 S6 C2C C1C 30(2) . . . . ? C2 S6 C2C C1C -39.1(19) . . . . ? C2C S6 C3 C4 5.8(15) . . . . ? C2 S6 C3 C4 26.0(11) . . . . ? C2C S6 C3 S4 -171.9(11) . . . . ? C2 S6 C3 S4 -151.6(6) . . . . ? C5 S4 C3 C4 1.2(9) . . . . ? C5 S4 C3 S6 179.2(6) . . . . ? S6 C3 C4 S3 -177.6(6) . . . . ? S4 C3 C4 S3 0.0(11) . . . . ? S6 C3 C4 S5 0.5(15) . . . . ? S4 C3 C4 S5 178.2(5) . . . . ? C5 S3 C4 C3 -1.2(9) . . . . ? C5 S3 C4 S5 -179.6(5) . . . . ? C1 S5 C4 C3 -1.7(10) . . . . ? C1C S5 C4 C3 -31.7(11) . . . . ? C1 S5 C4 S3 176.6(5) . . . . ? C1C S5 C4 S3 146.6(8) . . . . ? C3 S4 C5 C6 -178.9(7) . . . . ? C3 S4 C5 S3 -2.0(6) . . . . ? C4 S3 C5 C6 178.8(7) . . . . ? C4 S3 C5 S4 2.0(6) . . . . ? S4 C5 C6 S2 0.2(11) . . . . ? S3 C5 C6 S2 -176.4(6) . . . . ? S4 C5 C6 S1 179.3(5) . . . . ? S3 C5 C6 S1 2.7(11) . . . . ? C7 S2 C6 C5 -177.0(8) . . . . ? C7 S2 C6 S1 3.9(7) . . . . ? C8 S1 C6 C5 177.3(7) . . . . ? C8 S1 C6 S2 -3.6(6) . . . . ? C6 S2 C7 C8 -2.8(9) . . . . ? C6 S2 C7 I2 177.5(5) . . . . ? S2 C7 C8 S1 0.7(11) . . . . ? I2 C7 C8 S1 -179.6(5) . . . . ? S2 C7 C8 I1 178.1(5) . . . . ? I2 C7 C8 I1 -2.2(13) . . . . ? C6 S1 C8 C7 1.7(8) . . . . ? C6 S1 C8 I1 -176.0(5) . . . . ? C12 S7 C9 C10 54.9(12) . . . . ? S7 C9 C10 S10 -56.9(17) . . . . ? C11 S10 C10 C9 22.2(16) . . . . ? C10 S10 C11 C12 8.9(12) . . . . ? C10 S10 C11 S9 -168.7(7) . . . . ? C13 S9 C11 C12 0.7(8) . . . . ? C13 S9 C11 S10 178.7(6) . . . . ? S10 C11 C12 S8 -178.3(6) . . . . ? S9 C11 C12 S8 -0.8(11) . . . . ? S10 C11 C12 S7 -0.6(14) . . . . ? S9 C11 C12 S7 177.0(5) . . . . ? C13 S8 C12 C11 0.4(9) . . . . ? C13 S8 C12 S7 -177.6(5) . . . . ? C9 S7 C12 C11 -28.8(10) . . . . ? C9 S7 C12 S8 149.0(6) . . . . ? C11 S9 C13 C14 177.2(8) . . . . ? C11 S9 C13 S8 -0.5(7) . . . . ? C12 S8 C13 C14 -177.5(8) . . . . ? C12 S8 C13 S9 0.2(6) . . . . ? S9 C13 C14 S12 2.2(12) . . . . ? S8 C13 C14 S12 179.7(6) . . . . ? S9 C13 C14 S11 178.8(6) . . . . ? S8 C13 C14 S11 -3.7(12) . . . . ? C15 S12 C14 C13 -177.5(8) . . . . ? C15 S12 C14 S11 5.7(6) . . . . ? C16 S11 C14 C13 178.0(8) . . . . ? C16 S11 C14 S12 -5.1(6) . . . . ? C14 S12 C15 C16 -4.3(9) . . . . ? C14 S12 C15 I4 177.9(5) . . . . ? S12 C15 C16 S11 1.3(11) . . . . ? I4 C15 C16 S11 178.9(4) . . . . ? S12 C15 C16 I3 179.7(5) . . . . ? I4 C15 C16 I3 -2.7(13) . . . . ? C14 S11 C16 C15 2.3(8) . . . . ? C14 S11 C16 I3 -176.3(5) . . . . ? O4 C1A C2A C3A 177.0(14) . . . . ? C6A C1A C2A C3A -6.4(13) . . . . ? C1A C2A C3A C7A 39.9(16) . . . . ? C1A C2A C3A C4A -70.7(12) . . . . ? C2A C3A C4A C5A 76.5(13) . . . . ? C7A C3A C4A C5A -38.6(12) . . . . ? C3A C4A C5A C6A 4.0(13) . . . . ? C4A C5A C6A C10A 171.4(10) . . . . ? C4A C5A C6A C7A 30.8(14) . . . . ? C4A C5A C6A C1A -70.7(11) . . . . ? O4 C1A C6A C10A 18.8(15) . . . . ? C2A C1A C6A C10A -158.3(10) . . . . ? O4 C1A C6A C7A 151.0(11) . . . . ? C2A C1A C6A C7A -26.1(11) . . . . ? O4 C1A C6A C5A -104.6(12) . . . . ? C2A C1A C6A C5A 78.3(11) . . . . ? C2A C3A C7A C9A 176.1(13) . . . . ? C4A C3A C7A C9A -68.7(14) . . . . ? C2A C3A C7A C6A -57.7(14) . . . . ? C4A C3A C7A C6A 57.5(10) . . . . ? C2A C3A C7A C8A 50.5(16) . . . . ? C4A C3A C7A C8A 165.7(8) . . . . ? C10A C6A C7A C3A 168.3(10) . . . . ? C5A C6A C7A C3A -54.7(13) . . . . ? C1A C6A C7A C3A 46.2(10) . . . . ? C10A C6A C7A C9A -72.4(16) . . . . ? C5A C6A C7A C9A 64.5(18) . . . . ? C1A C6A C7A C9A 165.4(14) . . . . ? C10A C6A C7A C8A 49.1(14) . . . . ? C5A C6A C7A C8A -173.9(11) . . . . ? C1A C6A C7A C8A -73.0(12) . . . . ? C7A C6A C10A S13A 98.3(12) . . . . ? C5A C6A C10A S13A -33.0(17) . . . . ? C1A C6A C10A S13A -144.5(9) . . . . ? C6A C10A S13A O1A -171.0(13) . . . . ? C6A C10A S13A O2A -49.2(17) . . . . ? C6A C10A S13A O3A 70.1(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.809 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.084