# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_13sd050 _audit_creation_date 2013-12-02T18:20:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C18 H18 N2 S6' _chemical_formula_moiety 'C18 H18 N2 S6' _chemical_formula_weight 454.7 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.15364(18) _cell_length_b 7.3059(2) _cell_length_c 19.4670(5) _cell_angle_alpha 91.284(2) _cell_angle_beta 90.918(2) _cell_angle_gamma 102.456(2) _cell_volume 992.99(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12269 _cell_measurement_theta_min 2.084 _cell_measurement_theta_max 29.51 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.4549 _exptl_crystal_size_mid 0.1313 _exptl_crystal_size_min 0.0395 _exptl_crystal_density_diffrn 1.521 _exptl_crystal_F_000 472 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0197 0 0 -1 0.0197 0 -1 0 0.0656 0 1 0 0.0656 10 -3 1 0.2202 -10 3 -1 0.2202 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_absorpt_correction_T_min 1.029 _exptl_absorpt_correction_T_max 1.491 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 0.0025192 _diffrn_orient_matrix_ub_12 -0.0035932 _diffrn_orient_matrix_ub_13 -0.0364072 _diffrn_orient_matrix_ub_21 0.0105202 _diffrn_orient_matrix_ub_22 0.0987376 _diffrn_orient_matrix_ub_23 -0.0005547 _diffrn_orient_matrix_ub_31 0.1009877 _diffrn_orient_matrix_ub_32 0.0114229 _diffrn_orient_matrix_ub_33 0.0017489 _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_number 24762 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.093 _diffrn_reflns_theta_max 28.279 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _diffrn_reflns_Laue_measured_fraction_full 1 _diffrn_reflns_Laue_measured_fraction_max 1 _diffrn_reflns_point_group_measured_fraction_full 1 _diffrn_reflns_point_group_measured_fraction_max 1 _reflns_number_total 4913 _reflns_number_gt 4315 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _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^)+(0.0301P)^2^+0.3918P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4913 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.332 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.047 _iucr_refine_instructions_details ; TITL 13sd050 in P-1 CELL 0.71073 7.15364 7.3059 19.4670 91.284 90.918 102.456 ZERR 2.00 0.00018 0.0002 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N S UNIT 36 36 4 12 TEMP -100.00 MERG 2 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 10 WGHT 0.030100 0.391800 FVAR 4.70593 N1 3 0.651031 1.082032 1.151485 11.00000 0.02763 0.03839 = 0.02173 0.00068 -0.00197 0.01228 N2 3 0.839508 1.403240 1.080935 11.00000 0.02554 0.02756 = 0.03036 -0.00687 -0.00312 0.00495 S1 4 0.681792 0.662650 0.938556 11.00000 0.02689 0.01848 = 0.02521 0.00034 -0.00065 0.00259 S2 4 0.856505 1.001006 0.861928 11.00000 0.02619 0.02087 = 0.02269 -0.00088 0.00231 0.00070 S3 4 0.648670 0.411025 0.798571 11.00000 0.03315 0.02088 = 0.02881 -0.00248 -0.00227 0.00385 S4 4 0.821134 0.743495 0.721288 11.00000 0.03511 0.02808 = 0.02551 -0.00278 0.00184 -0.00242 S5 4 0.485125 0.185082 0.671926 11.00000 0.03814 0.02742 = 0.04726 -0.01539 -0.01046 0.00582 S6 4 0.693611 0.560593 0.584012 11.00000 0.04880 0.04425 = 0.02470 -0.00746 -0.00032 0.01613 C1 1 0.756388 0.759622 0.859419 11.00000 0.01948 0.02010 = 0.02439 0.00003 -0.00089 0.00344 C2 1 0.712665 0.877076 0.983851 11.00000 0.01654 0.01985 = 0.02446 -0.00049 -0.00379 0.00362 C3 1 0.662462 0.891422 1.050987 11.00000 0.01999 0.02449 = 0.02429 0.00384 -0.00106 0.00412 AFIX 43 H3 2 0.602286 0.783014 1.074760 11.00000 -1.20000 AFIX 0 C4 1 0.701321 1.069671 1.084498 11.00000 0.01906 0.02936 = 0.02185 0.00051 -0.00367 0.00815 C5 1 0.695837 1.250354 1.180469 11.00000 0.03117 0.04374 = 0.02308 -0.00529 -0.00341 0.01433 AFIX 43 H5 2 0.663163 1.265162 1.227066 11.00000 -1.20000 AFIX 0 C6 1 0.790072 1.409802 1.145622 11.00000 0.02929 0.03502 = 0.03062 -0.01106 -0.00507 0.00873 AFIX 43 H6 2 0.819211 1.527147 1.169848 11.00000 -1.20000 AFIX 0 C7 1 0.794347 1.230231 1.049002 11.00000 0.01736 0.02481 = 0.02560 -0.00264 -0.00398 0.00441 C8 1 0.843586 1.213257 0.979489 11.00000 0.02027 0.02104 = 0.02556 0.00140 -0.00019 0.00283 AFIX 43 H8 2 0.904673 1.320420 0.955233 11.00000 -1.20000 AFIX 0 C9 1 0.801724 1.039585 0.947659 11.00000 0.01656 0.02263 = 0.02183 -0.00007 -0.00137 0.00459 C10 1 0.742149 0.654569 0.801190 11.00000 0.02260 0.02128 = 0.02589 -0.00081 -0.00248 0.00299 C11 1 0.604349 0.399264 0.708977 11.00000 0.02622 0.02640 = 0.03041 -0.00804 -0.00466 0.00730 C12 1 0.685081 0.551390 0.673532 11.00000 0.02927 0.02984 = 0.02588 -0.00716 -0.00336 0.00817 C13 1 0.568068 0.744699 0.564266 11.00000 0.04558 0.03011 = 0.02654 0.00189 -0.00215 0.00250 AFIX 23 H13A 2 0.631881 0.861018 0.589580 11.00000 -1.20000 H13B 2 0.578676 0.769511 0.514536 11.00000 -1.20000 AFIX 0 C14 1 0.358709 0.699021 0.582240 11.00000 0.04668 0.03375 = 0.03236 0.00255 0.00019 0.00661 AFIX 23 H14A 2 0.346992 0.711050 0.632660 11.00000 -1.20000 H14B 2 0.302126 0.567417 0.568167 11.00000 -1.20000 AFIX 0 C15 1 0.248171 0.827378 0.547326 11.00000 0.05512 0.04011 = 0.04696 -0.00522 -0.01141 0.01299 AFIX 137 H15A 2 0.305036 0.957972 0.560563 11.00000 -1.50000 H15B 2 0.114432 0.796342 0.561488 11.00000 -1.50000 H15C 2 0.253582 0.810800 0.497356 11.00000 -1.50000 AFIX 0 C16 1 0.256890 0.146490 0.715167 11.00000 0.03984 0.03141 = 0.03619 0.00657 -0.00992 -0.00704 AFIX 23 H16A 2 0.189420 0.014451 0.706713 11.00000 -1.20000 H16B 2 0.282266 0.164654 0.765273 11.00000 -1.20000 AFIX 0 C17 1 0.125579 0.272403 0.693323 11.00000 0.03645 0.03954 = 0.03332 -0.00100 0.00251 0.00330 AFIX 23 H17A 2 0.197279 0.404403 0.696676 11.00000 -1.20000 H17B 2 0.018143 0.258484 0.725586 11.00000 -1.20000 AFIX 0 C18 1 0.044790 0.230856 0.620869 11.00000 0.04060 0.04338 = 0.04136 -0.00022 -0.00928 0.01112 AFIX 137 H18A 2 0.150146 0.240861 0.588642 11.00000 -1.50000 H18B 2 -0.033142 0.321217 0.609119 11.00000 -1.50000 H18C 2 -0.034901 0.103611 0.617972 11.00000 -1.50000 AFIX 0 HKLF 4 REM 13sd050 in P-1 REM R1 = 0.0274 for 4315 Fo > 4sig(Fo) and 0.0331 for all 4913 data REM 237 parameters refined using 0 restraints END ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.65103(18) 1.08203(18) 1.15148(6) 0.0285(3) Uani 1 d . . N2 N 0.83951(17) 1.40324(17) 1.08094(6) 0.0281(3) Uani 1 d . . S1 S 0.68179(5) 0.66265(5) 0.93856(2) 0.02389(8) Uani 1 d . . S2 S 0.85651(5) 1.00101(5) 0.86193(2) 0.02391(8) Uani 1 d . . S3 S 0.64867(5) 0.41103(5) 0.79857(2) 0.02799(9) Uani 1 d . . S4 S 0.82113(6) 0.74350(5) 0.72129(2) 0.03100(9) Uani 1 d . . S5 S 0.48513(6) 0.18508(6) 0.67193(2) 0.03817(11) Uani 1 d . . S6 S 0.69361(7) 0.56059(6) 0.58401(2) 0.03848(11) Uani 1 d . . C1 C 0.75639(19) 0.75962(18) 0.85942(7) 0.0215(3) Uani 1 d . . C2 C 0.71267(18) 0.87708(18) 0.98385(7) 0.0204(3) Uani 1 d . . C3 C 0.66246(19) 0.89142(19) 1.05099(7) 0.0230(3) Uani 1 d . . H3 H 0.6023 0.783 1.0748 0.028 Uiso 1 calc . . C4 C 0.70132(19) 1.0697(2) 1.08450(7) 0.0230(3) Uani 1 d . . C5 C 0.6958(2) 1.2504(2) 1.18047(8) 0.0319(3) Uani 1 d . . H5 H 0.6632 1.2652 1.2271 0.038 Uiso 1 calc . . C6 C 0.7901(2) 1.4098(2) 1.14562(8) 0.0316(3) Uani 1 d . . H6 H 0.8192 1.5271 1.1698 0.038 Uiso 1 calc . . C7 C 0.79435(19) 1.23023(19) 1.04900(7) 0.0227(3) Uani 1 d . . C8 C 0.84359(19) 1.21326(18) 0.97949(7) 0.0225(3) Uani 1 d . . H8 H 0.9047 1.3204 0.9552 0.027 Uiso 1 calc . . C9 C 0.80172(18) 1.03959(18) 0.94766(7) 0.0203(3) Uani 1 d . . C10 C 0.7421(2) 0.65457(19) 0.80119(7) 0.0236(3) Uani 1 d . . C11 C 0.6043(2) 0.3993(2) 0.70898(7) 0.0276(3) Uani 1 d . . C12 C 0.6851(2) 0.5514(2) 0.67353(7) 0.0282(3) Uani 1 d . . C13 C 0.5681(2) 0.7447(2) 0.56427(8) 0.0349(3) Uani 1 d . . H13A H 0.6319 0.861 0.5896 0.042 Uiso 1 calc . . H13B H 0.5787 0.7695 0.5145 0.042 Uiso 1 calc . . C14 C 0.3587(3) 0.6990(2) 0.58224(8) 0.0379(4) Uani 1 d . . H14A H 0.347 0.711 0.6327 0.045 Uiso 1 calc . . H14B H 0.3021 0.5674 0.5682 0.045 Uiso 1 calc . . C15 C 0.2482(3) 0.8274(3) 0.54733(10) 0.0472(4) Uani 1 d . . H15A H 0.305 0.958 0.5606 0.071 Uiso 1 calc . . H15B H 0.1144 0.7963 0.5615 0.071 Uiso 1 calc . . H15C H 0.2536 0.8108 0.4974 0.071 Uiso 1 calc . . C16 C 0.2569(2) 0.1465(2) 0.71517(9) 0.0381(4) Uani 1 d . . H16A H 0.1894 0.0145 0.7067 0.046 Uiso 1 calc . . H16B H 0.2823 0.1647 0.7653 0.046 Uiso 1 calc . . C17 C 0.1256(2) 0.2724(2) 0.69332(8) 0.0372(4) Uani 1 d . . H17A H 0.1973 0.4044 0.6967 0.045 Uiso 1 calc . . H17B H 0.0181 0.2585 0.7256 0.045 Uiso 1 calc . . C18 C 0.0448(3) 0.2309(3) 0.62087(9) 0.0416(4) Uani 1 d . . H18A H 0.1501 0.2409 0.5886 0.062 Uiso 1 calc . . H18B H -0.0331 0.3212 0.6091 0.062 Uiso 1 calc . . H18C H -0.0349 0.1036 0.618 0.062 Uiso 1 calc . . 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 N1 0.0276(6) 0.0384(7) 0.0217(6) 0.0007(5) -0.0020(5) 0.0123(5) N2 0.0255(6) 0.0276(6) 0.0304(6) -0.0069(5) -0.0031(5) 0.0050(5) S1 0.02689(18) 0.01848(15) 0.02521(16) 0.00034(12) -0.00065(13) 0.00259(13) S2 0.02619(17) 0.02087(16) 0.02269(16) -0.00088(12) 0.00231(13) 0.00070(13) S3 0.0331(2) 0.02088(16) 0.02881(18) -0.00248(13) -0.00227(14) 0.00385(14) S4 0.0351(2) 0.02808(18) 0.02551(17) -0.00278(14) 0.00184(14) -0.00242(15) S5 0.0381(2) 0.02742(19) 0.0473(2) -0.01539(17) -0.01046(18) 0.00582(16) S6 0.0488(3) 0.0443(2) 0.02470(18) -0.00746(16) -0.00032(16) 0.01613(19) C1 0.0195(6) 0.0201(6) 0.0244(6) 0.0000(5) -0.0009(5) 0.0034(5) C2 0.0165(6) 0.0199(6) 0.0245(6) -0.0005(5) -0.0038(5) 0.0036(5) C3 0.0200(6) 0.0245(6) 0.0243(6) 0.0038(5) -0.0011(5) 0.0041(5) C4 0.0191(6) 0.0294(7) 0.0219(6) 0.0005(5) -0.0037(5) 0.0081(5) C5 0.0312(8) 0.0437(9) 0.0231(7) -0.0053(6) -0.0034(6) 0.0143(7) C6 0.0293(8) 0.0350(8) 0.0306(7) -0.0111(6) -0.0051(6) 0.0087(6) C7 0.0174(6) 0.0248(6) 0.0256(6) -0.0026(5) -0.0040(5) 0.0044(5) C8 0.0203(6) 0.0210(6) 0.0256(6) 0.0014(5) -0.0002(5) 0.0028(5) C9 0.0166(6) 0.0226(6) 0.0218(6) -0.0001(5) -0.0014(5) 0.0046(5) C10 0.0226(6) 0.0213(6) 0.0259(6) -0.0008(5) -0.0025(5) 0.0030(5) C11 0.0262(7) 0.0264(7) 0.0304(7) -0.0080(6) -0.0047(6) 0.0073(6) C12 0.0293(7) 0.0298(7) 0.0259(7) -0.0072(6) -0.0034(6) 0.0082(6) C13 0.0456(9) 0.0301(8) 0.0265(7) 0.0019(6) -0.0022(6) 0.0025(7) C14 0.0467(10) 0.0337(8) 0.0324(8) 0.0026(6) 0.0002(7) 0.0066(7) C15 0.0551(12) 0.0401(10) 0.0470(10) -0.0052(8) -0.0114(9) 0.0130(9) C16 0.0398(9) 0.0314(8) 0.0362(8) 0.0066(6) -0.0099(7) -0.0070(7) C17 0.0365(9) 0.0395(9) 0.0333(8) -0.0010(7) 0.0025(7) 0.0033(7) C18 0.0406(9) 0.0434(10) 0.0414(9) -0.0002(7) -0.0093(7) 0.0111(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C5 1.314(2) . ? N1 C4 1.3645(17) . ? N2 C6 1.3160(19) . ? N2 C7 1.3677(17) . ? S1 C2 1.7501(13) . ? S1 C1 1.7528(14) . ? S2 C9 1.7510(13) . ? S2 C1 1.7537(14) . ? S3 C10 1.7599(14) . ? S3 C11 1.7646(15) . ? S4 C10 1.7538(14) . ? S4 C12 1.7620(15) . ? S5 C11 1.7465(14) . ? S5 C16 1.8193(18) . ? S6 C12 1.7470(15) . ? S6 C13 1.8157(17) . ? C1 C10 1.3446(19) . ? C2 C3 1.3686(18) . ? C2 C9 1.4274(18) . ? C3 C4 1.4138(19) . ? C3 H3 0.95 . ? C4 C7 1.418(2) . ? C5 C6 1.408(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.4132(18) . ? C8 C9 1.3706(18) . ? C8 H8 0.95 . ? C11 C12 1.347(2) . ? C13 C14 1.511(2) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.516(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 C17 1.512(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.515(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C4 115.80(13) . . ? C6 N2 C7 115.78(13) . . ? C2 S1 C1 95.74(6) . . ? C9 S2 C1 95.95(6) . . ? C10 S3 C11 94.27(7) . . ? C10 S4 C12 94.46(7) . . ? C11 S5 C16 101.64(7) . . ? C12 S6 C13 103.29(7) . . ? C10 C1 S1 122.05(11) . . ? C10 C1 S2 122.47(11) . . ? S1 C1 S2 115.46(7) . . ? C3 C2 C9 120.72(12) . . ? C3 C2 S1 123.04(10) . . ? C9 C2 S1 116.18(10) . . ? C2 C3 C4 119.14(13) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? N1 C4 C3 118.57(13) . . ? N1 C4 C7 121.37(13) . . ? C3 C4 C7 120.05(12) . . ? N1 C5 C6 123.01(14) . . ? N1 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? N2 C6 C5 122.82(14) . . ? N2 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? N2 C7 C8 118.69(13) . . ? N2 C7 C4 121.22(13) . . ? C8 C7 C4 120.09(12) . . ? C9 C8 C7 118.88(12) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C2 121.09(12) . . ? C8 C9 S2 123.03(10) . . ? C2 C9 S2 115.87(10) . . ? C1 C10 S4 123.81(11) . . ? C1 C10 S3 122.85(11) . . ? S4 C10 S3 113.31(8) . . ? C12 C11 S5 124.82(12) . . ? C12 C11 S3 116.65(11) . . ? S5 C11 S3 118.07(9) . . ? C11 C12 S6 125.02(11) . . ? C11 C12 S4 116.87(11) . . ? S6 C12 S4 117.46(9) . . ? C14 C13 S6 113.95(11) . . ? C14 C13 H13A 108.8 . . ? S6 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? S6 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 111.92(15) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 S5 115.04(11) . . ? C17 C16 H16A 108.5 . . ? S5 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? S5 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 113.61(14) . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C2 S1 C1 C10 -172.63(12) . . . . ? C2 S1 C1 S2 9.05(9) . . . . ? C9 S2 C1 C10 173.88(13) . . . . ? C9 S2 C1 S1 -7.81(9) . . . . ? C1 S1 C2 C3 175.40(12) . . . . ? C1 S1 C2 C9 -7.09(11) . . . . ? C9 C2 C3 C4 -0.51(19) . . . . ? S1 C2 C3 C4 176.90(10) . . . . ? C5 N1 C4 C3 178.06(13) . . . . ? C5 N1 C4 C7 -0.60(19) . . . . ? C2 C3 C4 N1 -179.83(12) . . . . ? C2 C3 C4 C7 -1.2(2) . . . . ? C4 N1 C5 C6 -0.1(2) . . . . ? C7 N2 C6 C5 -0.3(2) . . . . ? N1 C5 C6 N2 0.6(2) . . . . ? C6 N2 C7 C8 -179.94(13) . . . . ? C6 N2 C7 C4 -0.4(2) . . . . ? N1 C4 C7 N2 0.9(2) . . . . ? C3 C4 C7 N2 -177.73(12) . . . . ? N1 C4 C7 C8 -179.59(12) . . . . ? C3 C4 C7 C8 1.8(2) . . . . ? N2 C7 C8 C9 178.83(12) . . . . ? C4 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C2 -1.0(2) . . . . ? C7 C8 C9 S2 -179.76(10) . . . . ? C3 C2 C9 C8 1.6(2) . . . . ? S1 C2 C9 C8 -175.96(10) . . . . ? C3 C2 C9 S2 -179.52(10) . . . . ? S1 C2 C9 S2 2.90(14) . . . . ? C1 S2 C9 C8 -178.24(12) . . . . ? C1 S2 C9 C2 2.92(11) . . . . ? S1 C1 C10 S4 -178.04(8) . . . . ? S2 C1 C10 S4 0.16(19) . . . . ? S1 C1 C10 S3 -0.20(18) . . . . ? S2 C1 C10 S3 178.00(7) . . . . ? C12 S4 C10 C1 -161.84(13) . . . . ? C12 S4 C10 S3 20.14(9) . . . . ? C11 S3 C10 C1 161.43(13) . . . . ? C11 S3 C10 S4 -20.53(9) . . . . ? C16 S5 C11 C12 -126.76(14) . . . . ? C16 S5 C11 S3 61.32(10) . . . . ? C10 S3 C11 C12 13.02(13) . . . . ? C10 S3 C11 S5 -174.39(9) . . . . ? S5 C11 C12 S6 -2.5(2) . . . . ? S3 C11 C12 S6 169.51(9) . . . . ? S5 C11 C12 S4 -172.99(8) . . . . ? S3 C11 C12 S4 -0.97(17) . . . . ? C13 S6 C12 C11 120.53(14) . . . . ? C13 S6 C12 S4 -69.04(10) . . . . ? C10 S4 C12 C11 -11.67(13) . . . . ? C10 S4 C12 S6 177.11(9) . . . . ? C12 S6 C13 C14 -64.80(13) . . . . ? S6 C13 C14 C15 -163.78(12) . . . . ? C11 S5 C16 C17 72.06(13) . . . . ? S5 C16 C17 C18 69.54(17) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 958950' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_13sd012 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C36 H36 I3 N4 S12' _chemical_formula_moiety '2(C18 H18 N2 S6), I3' _chemical_formula_weight 1290.11 _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 7.59591(8) _cell_length_b 11.61481(13) _cell_length_c 25.9543(3) _cell_angle_alpha 83.0995(10) _cell_angle_beta 84.6415(9) _cell_angle_gamma 89.8152(9) _cell_volume 2263.22(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 65802 _cell_measurement_theta_min 1.754 _cell_measurement_theta_max 32.257 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.4711 _exptl_crystal_size_mid 0.2864 _exptl_crystal_size_min 0.0459 _exptl_crystal_density_diffrn 1.893 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1262 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 -1 0.1302 0 0 -1 0.0229 0 1 1 0.1272 0 0 1 0.0229 -9 7 -14 0.2063 -11 -1 -10 0.2739 10 -5 -7 0.2246 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 2.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.52378 _exptl_absorpt_correction_T_max 1 _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 -0.0216216 _diffrn_orient_matrix_ub_12 0.0593825 _diffrn_orient_matrix_ub_13 0.0003108 _diffrn_orient_matrix_ub_21 0.0090689 _diffrn_orient_matrix_ub_22 0.0081529 _diffrn_orient_matrix_ub_23 -0.0276476 _diffrn_orient_matrix_ub_31 -0.0908143 _diffrn_orient_matrix_ub_32 -0.0138379 _diffrn_orient_matrix_ub_33 -0.0001598 _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_unetI/netI 0.0168 _diffrn_reflns_number 161756 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 30.51 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 13791 _reflns_number_gt 12163 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _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^)+(0.0149P)^2^+3.3282P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 13791 _refine_ls_number_parameters 529 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.062 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.516 _refine_diff_density_min -1.31 _refine_diff_density_rms 0.083 _iucr_refine_instructions_details ; TITL 13sd012 CELL 0.71073 7.59591 11.61481 25.9543 83.0995 84.6415 89.8152 ZERR 2.00 0.00008 0.00013 0.0003 0.0010 0.0009 0.0009 LATT 1 SFAC C H N S I UNIT 72 72 8 24 6 MERG 2 SIMU 0.02 0.04 C13A > C15B DELU 0.01 0.01 C13A > C15A DELU 0.01 0.01 C13B > C15B FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 10 TEMP -100.00 WGHT 0.014900 3.328200 FVAR 2.11638 0.79944 C1 1 -0.108166 0.851260 0.494991 11.00000 0.03050 0.02676 = 0.02397 -0.00407 -0.00179 0.00497 AFIX 43 H1 2 -0.130631 0.909426 0.517506 11.00000 -1.20000 AFIX 0 C2 1 -0.170078 0.737288 0.512105 11.00000 0.02964 0.03127 = 0.02138 -0.00221 0.00127 0.00166 AFIX 43 H2 2 -0.234372 0.722300 0.545433 11.00000 -1.20000 AFIX 0 C3 1 0.008932 0.792504 0.418317 11.00000 0.02062 0.02164 = 0.01939 -0.00035 -0.00476 0.00194 C4 1 -0.050219 0.677507 0.436123 11.00000 0.01948 0.02285 = 0.01859 0.00012 -0.00310 -0.00093 C5 1 -0.012826 0.587717 0.404638 11.00000 0.02379 0.02037 = 0.02253 0.00029 -0.00264 -0.00244 AFIX 43 H5 2 -0.049244 0.510211 0.416685 11.00000 -1.20000 AFIX 0 C6 1 0.077025 0.614512 0.356358 11.00000 0.02308 0.01889 = 0.01868 -0.00122 -0.00417 -0.00104 C7 1 0.130331 0.730502 0.337276 11.00000 0.02082 0.02064 = 0.01814 0.00082 -0.00446 0.00202 C8 1 0.098949 0.818433 0.368010 11.00000 0.02430 0.01792 = 0.02153 0.00202 -0.00211 0.00079 AFIX 43 H8 2 0.137169 0.895429 0.355629 11.00000 -1.20000 AFIX 0 C9 1 0.238872 0.604571 0.264267 11.00000 0.02504 0.02134 = 0.01919 -0.00009 -0.00449 0.00106 C10 1 0.314271 0.565178 0.220499 11.00000 0.02622 0.02048 = 0.01854 -0.00167 -0.00451 0.00035 C11 1 0.465221 0.543339 0.128271 11.00000 0.02867 0.02272 = 0.01895 -0.00167 -0.00038 0.00314 C12 1 0.420713 0.434290 0.149651 11.00000 0.02962 0.02269 = 0.01837 -0.00288 -0.00311 0.00163 PART 1 C13A 1 0.422315 0.672508 0.031196 21.00000 0.03659 0.02483 = 0.02155 0.00240 -0.00393 0.00174 AFIX 23 H13A 2 0.418545 0.649471 -0.004193 21.00000 -1.20000 H13B 2 0.302550 0.660286 0.049642 21.00000 -1.20000 AFIX 0 C14A 1 0.468930 0.799635 0.026459 21.00000 0.04589 0.02817 = 0.03740 0.00292 -0.00847 -0.00158 AFIX 23 H14A 2 0.594283 0.811035 0.012514 21.00000 -1.20000 H14B 2 0.455080 0.826107 0.061464 21.00000 -1.20000 AFIX 0 C15A 1 0.352187 0.872532 -0.009283 21.00000 0.05250 0.03104 = 0.03828 0.01151 -0.00252 0.00492 AFIX 137 H15A 2 0.373525 0.851268 -0.044735 21.00000 -1.50000 H15B 2 0.380339 0.954880 -0.009498 21.00000 -1.50000 H15C 2 0.227647 0.858309 0.003406 21.00000 -1.50000 AFIX 0 PART 2 SAME C13A > C15A C13B 1 0.548463 0.714987 0.047282 -21.00000 0.04423 0.03141 = 0.02435 -0.00147 0.00250 -0.00471 AFIX 23 H13C 2 0.544522 0.760173 0.077368 -21.00000 -1.20000 H13D 2 0.646657 0.745584 0.021556 -21.00000 -1.20000 AFIX 0 C14B 1 0.378303 0.726213 0.023232 -21.00000 0.05004 0.02590 = 0.03725 0.00097 -0.00776 0.00615 AFIX 23 H14C 2 0.280492 0.700716 0.050070 -21.00000 -1.20000 H14D 2 0.379409 0.674262 -0.004370 -21.00000 -1.20000 AFIX 0 C15B 1 0.343770 0.850010 -0.000355 -21.00000 0.07502 0.03333 = 0.04332 0.00871 -0.00333 0.00337 AFIX 137 H15D 2 0.334683 0.901059 0.027205 -21.00000 -1.50000 H15E 2 0.232985 0.852097 -0.016992 -21.00000 -1.50000 H15F 2 0.441455 0.876403 -0.026431 -21.00000 -1.50000 AFIX 0 PART 0 C16 1 0.240142 0.276321 0.104200 11.00000 0.04452 0.03059 = 0.02933 -0.00614 -0.00151 -0.00746 AFIX 23 H16A 2 0.244857 0.205834 0.086142 11.00000 -1.20000 H16B 2 0.163097 0.258617 0.137124 11.00000 -1.20000 AFIX 0 C17 1 0.156785 0.372506 0.070415 11.00000 0.03744 0.04561 = 0.03825 -0.00695 -0.00547 0.00217 AFIX 23 H17A 2 0.240860 0.398947 0.039836 11.00000 -1.20000 H17B 2 0.132768 0.439031 0.090498 11.00000 -1.20000 AFIX 0 C18 1 -0.014879 0.333617 0.051716 11.00000 0.04864 0.08601 = 0.06130 -0.02447 -0.01923 -0.00159 AFIX 137 H18A 2 0.010250 0.273474 0.028670 11.00000 -1.50000 H18B 2 -0.070029 0.400006 0.032629 11.00000 -1.50000 H18C 2 -0.095436 0.302319 0.081805 11.00000 -1.50000 AFIX 0 C19 1 0.227627 0.882225 0.581229 11.00000 0.04024 0.02737 = 0.02690 -0.00582 -0.00296 0.00594 AFIX 43 H19 2 0.200512 0.941496 0.602879 11.00000 -1.20000 AFIX 0 C20 1 0.169077 0.767174 0.599525 11.00000 0.03463 0.03133 = 0.02244 -0.00124 -0.00288 0.00546 AFIX 43 H20 2 0.104014 0.752716 0.632758 11.00000 -1.20000 AFIX 0 C21 1 0.352886 0.821663 0.506135 11.00000 0.02571 0.01892 = 0.02303 -0.00102 -0.00543 0.00105 C22 1 0.295328 0.706410 0.524562 11.00000 0.02325 0.02035 = 0.02024 0.00156 -0.00335 0.00159 C23 1 0.332717 0.616432 0.493652 11.00000 0.02425 0.01793 = 0.02186 0.00281 -0.00328 -0.00125 AFIX 43 H23 2 0.295422 0.539129 0.505773 11.00000 -1.20000 AFIX 0 C24 1 0.424636 0.642792 0.445389 11.00000 0.02103 0.01780 = 0.02010 0.00067 -0.00473 0.00060 C25 1 0.478457 0.758493 0.426550 11.00000 0.01964 0.01968 = 0.02064 0.00264 -0.00446 -0.00086 C26 1 0.443552 0.847338 0.456309 11.00000 0.02742 0.01846 = 0.02523 0.00282 -0.00496 -0.00341 AFIX 43 H26 2 0.479844 0.924510 0.443530 11.00000 -1.20000 AFIX 0 C27 1 0.581684 0.632484 0.353791 11.00000 0.02187 0.02224 = 0.02108 0.00203 -0.00377 0.00083 C28 1 0.654416 0.594487 0.308180 11.00000 0.02358 0.02388 = 0.02013 0.00105 -0.00261 0.00119 C29 1 0.816660 0.585230 0.217544 11.00000 0.02437 0.02902 = 0.01864 0.00141 -0.00192 0.00201 C30 1 0.776916 0.472326 0.237066 11.00000 0.02579 0.02651 = 0.01941 0.00067 -0.00308 0.00455 C31 1 0.914404 0.782686 0.151154 11.00000 0.03921 0.03751 = 0.02891 0.00493 0.00228 0.00118 AFIX 23 H31A 2 0.791152 0.807962 0.158866 11.00000 -1.20000 H31B 2 0.987493 0.810708 0.176816 11.00000 -1.20000 AFIX 0 C32 1 0.983639 0.832668 0.096676 11.00000 0.05521 0.04647 = 0.03473 0.01176 0.00828 0.00167 AFIX 23 H32A 2 0.915045 0.800082 0.071138 11.00000 -1.20000 H32B 2 1.108779 0.810290 0.089918 11.00000 -1.20000 AFIX 0 C33 1 0.969902 0.964196 0.089473 11.00000 0.05503 0.04719 = 0.05489 0.02080 0.00448 0.00712 AFIX 137 H33A 2 0.845918 0.986449 0.095793 11.00000 -1.50000 H33B 2 1.014966 0.994215 0.053790 11.00000 -1.50000 H33C 2 1.039970 0.996666 0.114194 11.00000 -1.50000 AFIX 0 C34 1 0.843085 0.236659 0.251390 11.00000 0.03436 0.02692 = 0.02611 0.00387 -0.00333 -0.00049 AFIX 23 H34A 2 0.941352 0.252142 0.272181 11.00000 -1.20000 H34B 2 0.732785 0.227232 0.275076 11.00000 -1.20000 AFIX 0 C35 1 0.879440 0.126527 0.226054 11.00000 0.03327 0.02825 = 0.03641 0.00016 0.00045 0.00105 AFIX 23 H35A 2 0.995368 0.133367 0.205017 11.00000 -1.20000 H35B 2 0.787234 0.115502 0.202498 11.00000 -1.20000 AFIX 0 C36 1 0.880168 0.022030 0.267959 11.00000 0.03516 0.02937 = 0.06022 0.00989 0.00127 0.00314 AFIX 137 H36A 2 0.969487 0.034101 0.291736 11.00000 -1.50000 H36B 2 0.908078 -0.048157 0.251396 11.00000 -1.50000 H36C 2 0.763405 0.013201 0.287592 11.00000 -1.50000 AFIX 0 N1 3 -0.020514 0.880081 0.449049 11.00000 0.02962 0.02330 = 0.02588 -0.00348 -0.00097 0.00322 N2 3 -0.142573 0.650880 0.483879 11.00000 0.02820 0.02627 = 0.02142 -0.00006 0.00111 -0.00210 N3 3 0.317072 0.910105 0.535966 11.00000 0.03920 0.02181 = 0.02860 -0.00387 -0.00322 0.00196 N4 3 0.201556 0.680283 0.572228 11.00000 0.03223 0.02457 = 0.02177 0.00082 -0.00027 0.00033 S1 4 0.236126 0.751875 0.273680 11.00000 0.02915 0.01957 = 0.01882 0.00118 -0.00047 0.00120 S2 4 0.139000 0.508533 0.315840 11.00000 0.03331 0.01914 = 0.02109 -0.00236 -0.00048 -0.00310 S3 4 0.414994 0.655297 0.166718 11.00000 0.02937 0.01912 = 0.02182 -0.00001 -0.00182 0.00074 S4 4 0.323538 0.416752 0.213958 11.00000 0.03372 0.02000 = 0.02015 -0.00118 -0.00069 -0.00249 S5 4 0.580959 0.576560 0.066767 11.00000 0.04031 0.03447 = 0.02385 0.00174 0.00578 0.00380 S6 4 0.461909 0.308339 0.119980 11.00000 0.03963 0.02314 = 0.02666 -0.00609 -0.00330 0.00461 S7 4 0.585656 0.777840 0.363381 11.00000 0.02785 0.02124 = 0.02324 0.00242 0.00023 -0.00353 S8 4 0.480392 0.537730 0.404147 11.00000 0.02971 0.01848 = 0.02070 0.00053 -0.00065 0.00054 S9 4 0.745493 0.690317 0.256715 11.00000 0.03034 0.02440 = 0.02268 0.00179 0.00069 -0.00120 S10 4 0.662225 0.450116 0.298555 11.00000 0.03221 0.02322 = 0.02125 0.00229 0.00020 0.00296 S11 4 0.922477 0.624846 0.155946 11.00000 0.03420 0.03583 = 0.02200 0.00379 0.00255 0.00175 S12 4 0.821437 0.357467 0.200898 11.00000 0.03861 0.02985 = 0.02143 -0.00083 -0.00309 0.00971 I1 5 0.435576 -0.022830 0.156024 11.00000 0.06626 0.02466 = 0.03431 -0.00286 -0.00009 0.00045 I2 5 0.380094 0.073703 0.253363 11.00000 0.02521 0.02564 = 0.03041 0.00062 -0.00095 -0.00108 I3 5 0.333151 0.165915 0.353843 11.00000 0.05182 0.04967 = 0.03210 -0.00817 0.00338 -0.00399 HKLF 4 END ; 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C -0.1082(3) 0.8513(2) 0.49499(9) 0.0271(4) Uani 1 1 d . . . H1 H -0.1306 0.9094 0.5175 0.032 Uiso 1 1 calc R . . C2 C -0.1701(3) 0.7373(2) 0.51211(9) 0.0277(4) Uani 1 1 d . . . H2 H -0.2344 0.7223 0.5454 0.033 Uiso 1 1 calc R . . C3 C 0.0089(3) 0.79250(18) 0.41832(8) 0.0205(4) Uani 1 1 d . . . C4 C -0.0502(3) 0.67751(18) 0.43612(8) 0.0204(4) Uani 1 1 d . . . C5 C -0.0128(3) 0.58772(18) 0.40464(8) 0.0224(4) Uani 1 1 d . . . H5 H -0.0492 0.5102 0.4167 0.027 Uiso 1 1 calc R . . C6 C 0.0770(3) 0.61451(17) 0.35636(8) 0.0202(4) Uani 1 1 d . . . C7 C 0.1303(3) 0.73050(18) 0.33728(8) 0.0200(4) Uani 1 1 d . . . C8 C 0.0989(3) 0.81843(18) 0.36801(8) 0.0216(4) Uani 1 1 d . . . H8 H 0.1372 0.8954 0.3556 0.026 Uiso 1 1 calc R . . C9 C 0.2389(3) 0.60457(18) 0.26427(8) 0.0219(4) Uani 1 1 d . . . C10 C 0.3143(3) 0.56518(18) 0.22050(8) 0.0216(4) Uani 1 1 d . . . C11 C 0.4652(3) 0.54334(19) 0.12827(8) 0.0236(4) Uani 1 1 d . A . C12 C 0.4207(3) 0.43429(19) 0.14965(8) 0.0235(4) Uani 1 1 d . . . C13A C 0.4223(4) 0.6725(3) 0.03120(12) 0.0280(7) Uani 0.799(6) 1 d PDU A 1 H13A H 0.4185 0.6495 -0.0042 0.034 Uiso 0.799(6) 1 calc PR A 1 H13B H 0.3026 0.6603 0.0496 0.034 Uiso 0.799(6) 1 calc PR A 1 C14A C 0.4689(5) 0.7996(3) 0.02646(14) 0.0374(8) Uani 0.799(6) 1 d PDU A 1 H14A H 0.5943 0.811 0.0125 0.045 Uiso 0.799(6) 1 calc PR A 1 H14B H 0.4551 0.8261 0.0615 0.045 Uiso 0.799(6) 1 calc PR A 1 C15A C 0.3522(12) 0.8725(6) -0.0093(4) 0.0420(13) Uani 0.799(6) 1 d PDU A 1 H15A H 0.3735 0.8513 -0.0447 0.063 Uiso 0.799(6) 1 calc PR A 1 H15B H 0.3803 0.9549 -0.0095 0.063 Uiso 0.799(6) 1 calc PR A 1 H15C H 0.2276 0.8583 0.0034 0.063 Uiso 0.799(6) 1 calc PR A 1 C13B C 0.5485(17) 0.7150(11) 0.0473(5) 0.034(3) Uani 0.201(6) 1 d PDU A 2 H13C H 0.5445 0.7602 0.0774 0.041 Uiso 0.201(6) 1 calc PR A 2 H13D H 0.6467 0.7456 0.0216 0.041 Uiso 0.201(6) 1 calc PR A 2 C14B C 0.3783(19) 0.7262(12) 0.0232(6) 0.038(3) Uani 0.201(6) 1 d PDU A 2 H14C H 0.2805 0.7007 0.0501 0.045 Uiso 0.201(6) 1 calc PR A 2 H14D H 0.3794 0.6743 -0.0044 0.045 Uiso 0.201(6) 1 calc PR A 2 C15B C 0.344(6) 0.850(2) -0.0004(17) 0.052(7) Uani 0.201(6) 1 d PDU A 2 H15D H 0.3347 0.9011 0.0272 0.078 Uiso 0.201(6) 1 calc PR A 2 H15E H 0.233 0.8521 -0.017 0.078 Uiso 0.201(6) 1 calc PR A 2 H15F H 0.4415 0.8764 -0.0264 0.078 Uiso 0.201(6) 1 calc PR A 2 C16 C 0.2401(4) 0.2763(2) 0.10420(10) 0.0347(5) Uani 1 1 d . . . H16A H 0.2449 0.2058 0.0861 0.042 Uiso 1 1 calc R . . H16B H 0.1631 0.2586 0.1371 0.042 Uiso 1 1 calc R . . C17 C 0.1568(4) 0.3725(3) 0.07042(12) 0.0402(6) Uani 1 1 d . . . H17A H 0.2409 0.3989 0.0398 0.048 Uiso 1 1 calc R . . H17B H 0.1328 0.439 0.0905 0.048 Uiso 1 1 calc R . . C18 C -0.0149(5) 0.3336(4) 0.05172(16) 0.0631(10) Uani 1 1 d . . . H18A H 0.0102 0.2735 0.0287 0.095 Uiso 1 1 calc R . . H18B H -0.07 0.4 0.0326 0.095 Uiso 1 1 calc R . . H18C H -0.0954 0.3023 0.0818 0.095 Uiso 1 1 calc R . . C19 C 0.2276(4) 0.8822(2) 0.58123(10) 0.0313(5) Uani 1 1 d . . . H19 H 0.2005 0.9415 0.6029 0.038 Uiso 1 1 calc R . . C20 C 0.1691(3) 0.7672(2) 0.59953(9) 0.0296(5) Uani 1 1 d . . . H20 H 0.104 0.7527 0.6328 0.036 Uiso 1 1 calc R . . C21 C 0.3529(3) 0.82166(18) 0.50614(8) 0.0225(4) Uani 1 1 d . . . C22 C 0.2953(3) 0.70641(18) 0.52456(8) 0.0215(4) Uani 1 1 d . . . C23 C 0.3327(3) 0.61643(18) 0.49365(8) 0.0217(4) Uani 1 1 d . . . H23 H 0.2954 0.5391 0.5058 0.026 Uiso 1 1 calc R . . C24 C 0.4246(3) 0.64279(17) 0.44539(8) 0.0197(4) Uani 1 1 d . . . C25 C 0.4785(3) 0.75849(18) 0.42655(8) 0.0202(4) Uani 1 1 d . . . C26 C 0.4436(3) 0.84734(18) 0.45631(9) 0.0240(4) Uani 1 1 d . . . H26 H 0.4798 0.9245 0.4435 0.029 Uiso 1 1 calc R . . C27 C 0.5817(3) 0.63248(18) 0.35379(8) 0.0220(4) Uani 1 1 d . . . C28 C 0.6544(3) 0.59449(19) 0.30818(8) 0.0228(4) Uani 1 1 d . . . C29 C 0.8167(3) 0.5852(2) 0.21754(8) 0.0244(4) Uani 1 1 d . . . C30 C 0.7769(3) 0.47233(19) 0.23707(8) 0.0241(4) Uani 1 1 d . . . C31 C 0.9144(4) 0.7827(2) 0.15115(10) 0.0363(6) Uani 1 1 d . . . H31A H 0.7912 0.808 0.1589 0.044 Uiso 1 1 calc R . . H31B H 0.9875 0.8107 0.1768 0.044 Uiso 1 1 calc R . . C32 C 0.9836(5) 0.8327(3) 0.09668(12) 0.0476(7) Uani 1 1 d . . . H32A H 0.915 0.8001 0.0711 0.057 Uiso 1 1 calc R . . H32B H 1.1088 0.8103 0.0899 0.057 Uiso 1 1 calc R . . C33 C 0.9699(5) 0.9642(3) 0.08947(14) 0.0552(9) Uani 1 1 d . . . H33A H 0.8459 0.9864 0.0958 0.083 Uiso 1 1 calc R . . H33B H 1.015 0.9942 0.0538 0.083 Uiso 1 1 calc R . . H33C H 1.04 0.9967 0.1142 0.083 Uiso 1 1 calc R . . C34 C 0.8431(3) 0.2367(2) 0.25139(9) 0.0297(5) Uani 1 1 d . . . H34A H 0.9414 0.2521 0.2722 0.036 Uiso 1 1 calc R . . H34B H 0.7328 0.2272 0.2751 0.036 Uiso 1 1 calc R . . C35 C 0.8794(4) 0.1265(2) 0.22605(11) 0.0332(5) Uani 1 1 d . . . H35A H 0.9954 0.1334 0.205 0.04 Uiso 1 1 calc R . . H35B H 0.7872 0.1155 0.2025 0.04 Uiso 1 1 calc R . . C36 C 0.8802(4) 0.0220(2) 0.26796(13) 0.0432(7) Uani 1 1 d . . . H36A H 0.9695 0.0341 0.2917 0.065 Uiso 1 1 calc R . . H36B H 0.9081 -0.0482 0.2514 0.065 Uiso 1 1 calc R . . H36C H 0.7634 0.0132 0.2876 0.065 Uiso 1 1 calc R . . N1 N -0.0205(3) 0.88008(17) 0.44905(8) 0.0263(4) Uani 1 1 d . . . N2 N -0.1426(3) 0.65088(17) 0.48388(7) 0.0257(4) Uani 1 1 d . . . N3 N 0.3171(3) 0.91011(17) 0.53597(8) 0.0298(4) Uani 1 1 d . . . N4 N 0.2016(3) 0.68028(17) 0.57223(7) 0.0266(4) Uani 1 1 d . . . S1 S 0.23613(8) 0.75187(4) 0.27368(2) 0.02292(10) Uani 1 1 d . . . S2 S 0.13900(8) 0.50853(5) 0.31584(2) 0.02464(10) Uani 1 1 d . . . S3 S 0.41499(8) 0.65530(5) 0.16672(2) 0.02368(10) Uani 1 1 d . . . S4 S 0.32354(8) 0.41675(5) 0.21396(2) 0.02483(11) Uani 1 1 d . . . S5 S 0.58096(9) 0.57656(6) 0.06677(2) 0.03387(13) Uani 1 1 d . . . S6 S 0.46191(9) 0.30834(5) 0.11998(2) 0.02955(12) Uani 1 1 d . . . S7 S 0.58566(8) 0.77784(5) 0.36338(2) 0.02468(10) Uani 1 1 d . . . S8 S 0.48039(8) 0.53773(4) 0.40415(2) 0.02331(10) Uani 1 1 d . . . S9 S 0.74549(8) 0.69032(5) 0.25671(2) 0.02638(11) Uani 1 1 d . . . S10 S 0.66223(8) 0.45012(5) 0.29855(2) 0.02614(11) Uani 1 1 d . . . S11 S 0.92248(9) 0.62485(6) 0.15595(2) 0.03160(12) Uani 1 1 d . . . S12 S 0.82144(9) 0.35747(5) 0.20090(2) 0.03015(12) Uani 1 1 d . . . I1 I 0.43558(3) -0.022830(15) 0.156024(7) 0.04209(5) Uani 1 1 d . . . I2 I 0.38009(2) 0.073703(13) 0.253363(6) 0.02751(4) Uani 1 1 d . . . I3 I 0.33315(3) 0.165915(18) 0.353843(7) 0.04471(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 C1 0.0305(12) 0.0268(11) 0.0240(10) -0.0041(8) -0.0018(9) 0.0050(9) C2 0.0296(11) 0.0313(11) 0.0214(10) -0.0022(8) 0.0013(8) 0.0017(9) C3 0.0206(9) 0.0216(9) 0.0194(9) -0.0004(7) -0.0048(7) 0.0019(7) C4 0.0195(9) 0.0229(9) 0.0186(9) 0.0001(7) -0.0031(7) -0.0009(7) C5 0.0238(10) 0.0204(9) 0.0225(9) 0.0003(7) -0.0026(8) -0.0024(8) C6 0.0231(10) 0.0189(9) 0.0187(9) -0.0012(7) -0.0042(7) -0.0010(7) C7 0.0208(9) 0.0206(9) 0.0181(9) 0.0008(7) -0.0045(7) 0.0020(7) C8 0.0243(10) 0.0179(9) 0.0215(9) 0.0020(7) -0.0021(8) 0.0008(7) C9 0.0250(10) 0.0213(9) 0.0192(9) -0.0001(7) -0.0045(8) 0.0011(8) C10 0.0262(10) 0.0205(9) 0.0185(9) -0.0017(7) -0.0045(8) 0.0004(8) C11 0.0287(11) 0.0227(10) 0.0189(9) -0.0017(7) -0.0004(8) 0.0031(8) C12 0.0296(11) 0.0227(10) 0.0184(9) -0.0029(7) -0.0031(8) 0.0016(8) C13A 0.0366(17) 0.0248(15) 0.0215(13) 0.0024(11) -0.0039(11) 0.0017(12) C14A 0.046(2) 0.0282(15) 0.0374(17) 0.0029(12) -0.0085(14) -0.0016(13) C15A 0.052(3) 0.031(3) 0.038(3) 0.012(2) -0.003(2) 0.005(2) C13B 0.044(6) 0.031(5) 0.024(5) -0.001(4) 0.003(4) -0.005(5) C14B 0.050(7) 0.026(6) 0.037(6) 0.001(5) -0.008(5) 0.006(5) C15B 0.075(13) 0.033(10) 0.043(14) 0.009(9) -0.003(10) 0.003(10) C16 0.0445(15) 0.0306(12) 0.0293(12) -0.0061(9) -0.0015(11) -0.0075(11) C17 0.0374(14) 0.0456(15) 0.0383(14) -0.0070(12) -0.0055(11) 0.0022(12) C18 0.049(2) 0.086(3) 0.061(2) -0.024(2) -0.0192(17) -0.0016(19) C19 0.0402(14) 0.0274(11) 0.0269(11) -0.0058(9) -0.0030(10) 0.0059(10) C20 0.0346(12) 0.0313(11) 0.0224(10) -0.0012(9) -0.0029(9) 0.0055(9) C21 0.0257(10) 0.0189(9) 0.0230(10) -0.0010(7) -0.0054(8) 0.0010(8) C22 0.0233(10) 0.0203(9) 0.0202(9) 0.0016(7) -0.0034(8) 0.0016(7) C23 0.0242(10) 0.0179(9) 0.0219(9) 0.0028(7) -0.0033(8) -0.0013(7) C24 0.0210(9) 0.0178(9) 0.0201(9) 0.0007(7) -0.0047(7) 0.0006(7) C25 0.0196(9) 0.0197(9) 0.0206(9) 0.0026(7) -0.0045(7) -0.0009(7) C26 0.0274(11) 0.0185(9) 0.0252(10) 0.0028(7) -0.0050(8) -0.0034(8) C27 0.0219(10) 0.0222(9) 0.0211(9) 0.0020(7) -0.0038(8) 0.0008(7) C28 0.0236(10) 0.0239(10) 0.0201(9) 0.0011(7) -0.0026(8) 0.0012(8) C29 0.0244(10) 0.0290(11) 0.0186(9) 0.0014(8) -0.0019(8) 0.0020(8) C30 0.0258(10) 0.0265(10) 0.0194(9) 0.0007(8) -0.0031(8) 0.0045(8) C31 0.0392(14) 0.0375(13) 0.0289(12) 0.0049(10) 0.0023(10) 0.0012(11) C32 0.0552(19) 0.0465(16) 0.0347(14) 0.0118(12) 0.0083(13) 0.0017(14) C33 0.055(2) 0.0472(18) 0.055(2) 0.0208(15) 0.0045(16) 0.0071(15) C34 0.0344(12) 0.0269(11) 0.0261(11) 0.0039(8) -0.0033(9) -0.0005(9) C35 0.0333(13) 0.0282(11) 0.0364(13) 0.0002(10) 0.0005(10) 0.0011(10) C36 0.0352(14) 0.0294(13) 0.0602(19) 0.0099(12) 0.0013(13) 0.0031(11) N1 0.0296(10) 0.0233(9) 0.0259(9) -0.0035(7) -0.0010(8) 0.0032(7) N2 0.0282(10) 0.0263(9) 0.0214(9) -0.0001(7) 0.0011(7) -0.0021(7) N3 0.0392(12) 0.0218(9) 0.0286(10) -0.0039(7) -0.0032(8) 0.0020(8) N4 0.0322(10) 0.0246(9) 0.0218(9) 0.0008(7) -0.0003(7) 0.0003(8) S1 0.0292(3) 0.0196(2) 0.0188(2) 0.00118(17) -0.00047(19) 0.00120(19) S2 0.0333(3) 0.0191(2) 0.0211(2) -0.00236(18) -0.0005(2) -0.0031(2) S3 0.0294(3) 0.0191(2) 0.0218(2) -0.00001(18) -0.0018(2) 0.00074(19) S4 0.0337(3) 0.0200(2) 0.0201(2) -0.00118(18) -0.0007(2) -0.0025(2) S5 0.0403(3) 0.0345(3) 0.0239(3) 0.0017(2) 0.0058(2) 0.0038(3) S6 0.0396(3) 0.0231(2) 0.0267(3) -0.0061(2) -0.0033(2) 0.0046(2) S7 0.0278(3) 0.0212(2) 0.0232(2) 0.00242(19) 0.0002(2) -0.0035(2) S8 0.0297(3) 0.0185(2) 0.0207(2) 0.00053(18) -0.0006(2) 0.00054(19) S9 0.0303(3) 0.0244(2) 0.0227(2) 0.00179(19) 0.0007(2) -0.0012(2) S10 0.0322(3) 0.0232(2) 0.0213(2) 0.00229(19) 0.0002(2) 0.0030(2) S11 0.0342(3) 0.0358(3) 0.0220(3) 0.0038(2) 0.0025(2) 0.0017(2) S12 0.0386(3) 0.0299(3) 0.0214(2) -0.0008(2) -0.0031(2) 0.0097(2) I1 0.06626(13) 0.02466(8) 0.03431(9) -0.00286(6) -0.00009(8) 0.00045(8) I2 0.02521(7) 0.02564(7) 0.03041(7) 0.00062(5) -0.00095(5) -0.00108(5) I3 0.05182(12) 0.04967(11) 0.03210(9) -0.00817(8) 0.00338(8) -0.00399(9) _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 C1 N1 1.317(3) . ? C1 C2 1.412(3) . ? C1 H1 0.95 . ? C2 N2 1.317(3) . ? C2 H2 0.95 . ? C3 N1 1.372(3) . ? C3 C8 1.415(3) . ? C3 C4 1.420(3) . ? C4 N2 1.368(3) . ? C4 C5 1.413(3) . ? C5 C6 1.371(3) . ? C5 H5 0.95 . ? C6 C7 1.425(3) . ? C6 S2 1.749(2) . ? C7 C8 1.377(3) . ? C7 S1 1.757(2) . ? C8 H8 0.95 . ? C9 C10 1.353(3) . ? C9 S2 1.752(2) . ? C9 S1 1.757(2) . ? C10 S4 1.753(2) . ? C10 S3 1.756(2) . ? C11 C12 1.351(3) . ? C11 S5 1.750(2) . ? C11 S3 1.752(2) . ? C12 S6 1.748(2) . ? C12 S4 1.750(2) . ? C13A C14A 1.507(4) . ? C13A S5 1.870(3) . ? C13A H13A 0.99 . ? C13A H13B 0.99 . ? C14A C15A 1.524(7) . ? C14A H14A 0.99 . ? C14A H14B 0.99 . ? C15A H15A 0.98 . ? C15A H15B 0.98 . ? C15A H15C 0.98 . ? C13B C14B 1.486(14) . ? C13B S5 1.651(12) . ? C13B H13C 0.99 . ? C13B H13D 0.99 . ? C14B C15B 1.525(17) . ? C14B H14C 0.99 . ? C14B H14D 0.99 . ? C15B H15D 0.98 . ? C15B H15E 0.98 . ? C15B H15F 0.98 . ? C16 C17 1.511(4) . ? C16 S6 1.820(3) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.521(4) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 N3 1.307(3) . ? C19 C20 1.422(3) . ? C19 H19 0.95 . ? C20 N4 1.311(3) . ? C20 H20 0.95 . ? C21 N3 1.371(3) . ? C21 C26 1.406(3) . ? C21 C22 1.422(3) . ? C22 N4 1.370(3) . ? C22 C23 1.405(3) . ? C23 C24 1.377(3) . ? C23 H23 0.95 . ? C24 C25 1.421(3) . ? C24 S8 1.744(2) . ? C25 C26 1.372(3) . ? C25 S7 1.751(2) . ? C26 H26 0.95 . ? C27 C28 1.380(3) . ? C27 S8 1.727(2) . ? C27 S7 1.737(2) . ? C28 S10 1.725(2) . ? C28 S9 1.725(2) . ? C29 C30 1.372(3) . ? C29 S11 1.732(2) . ? C29 S9 1.734(2) . ? C30 S12 1.736(2) . ? C30 S10 1.736(2) . ? C31 C32 1.510(4) . ? C31 S11 1.824(3) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 C33 1.521(4) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? C34 C35 1.520(4) . ? C34 S12 1.819(2) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 C36 1.530(4) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 H36A 0.98 . ? C36 H36B 0.98 . ? C36 H36C 0.98 . ? I1 I2 2.8803(2) . ? I2 I3 2.9275(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.6(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? N2 C2 C1 122.9(2) . . ? N2 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? N1 C3 C8 118.91(19) . . ? N1 C3 C4 121.06(19) . . ? C8 C3 C4 120.03(19) . . ? N2 C4 C5 118.64(19) . . ? N2 C4 C3 121.20(19) . . ? C5 C4 C3 120.16(19) . . ? C6 C5 C4 118.77(19) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 121.45(19) . . ? C5 C6 S2 122.19(16) . . ? C7 C6 S2 116.33(16) . . ? C8 C7 C6 120.46(19) . . ? C8 C7 S1 123.49(16) . . ? C6 C7 S1 116.06(16) . . ? C7 C8 C3 119.06(19) . . ? C7 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? C10 C9 S2 120.85(17) . . ? C10 C9 S1 123.19(17) . . ? S2 C9 S1 115.96(12) . . ? C9 C10 S4 121.72(17) . . ? C9 C10 S3 123.87(17) . . ? S4 C10 S3 114.39(12) . . ? C12 C11 S5 123.68(17) . . ? C12 C11 S3 117.16(17) . . ? S5 C11 S3 119.03(13) . . ? C11 C12 S6 125.78(17) . . ? C11 C12 S4 117.14(17) . . ? S6 C12 S4 116.99(12) . . ? C14A C13A S5 113.6(2) . . ? C14A C13A H13A 108.8 . . ? S5 C13A H13A 108.8 . . ? C14A C13A H13B 108.8 . . ? S5 C13A H13B 108.8 . . ? H13A C13A H13B 107.7 . . ? C13A C14A C15A 111.7(5) . . ? C13A C14A H14A 109.3 . . ? C15A C14A H14A 109.3 . . ? C13A C14A H14B 109.3 . . ? C15A C14A H14B 109.3 . . ? H14A C14A H14B 107.9 . . ? C14B C13B S5 108.6(9) . . ? C14B C13B H13C 110 . . ? S5 C13B H13C 110 . . ? C14B C13B H13D 110 . . ? S5 C13B H13D 110 . . ? H13C C13B H13D 108.3 . . ? C13B C14B C15B 112.7(19) . . ? C13B C14B H14C 109.1 . . ? C15B C14B H14C 109.1 . . ? C13B C14B H14D 109.1 . . ? C15B C14B H14D 109.1 . . ? H14C C14B H14D 107.8 . . ? C14B C15B H15D 109.5 . . ? C14B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C14B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C17 C16 S6 114.76(19) . . ? C17 C16 H16A 108.6 . . ? S6 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? S6 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 112.0(3) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C20 122.9(2) . . ? N3 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? N4 C20 C19 122.4(2) . . ? N4 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? N3 C21 C26 118.8(2) . . ? N3 C21 C22 120.7(2) . . ? C26 C21 C22 120.4(2) . . ? N4 C22 C23 118.41(19) . . ? N4 C22 C21 121.4(2) . . ? C23 C22 C21 120.23(19) . . ? C24 C23 C22 118.51(19) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C23 C24 C25 121.16(19) . . ? C23 C24 S8 122.37(16) . . ? C25 C24 S8 116.46(16) . . ? C26 C25 C24 121.07(19) . . ? C26 C25 S7 123.64(16) . . ? C24 C25 S7 115.28(16) . . ? C25 C26 C21 118.56(19) . . ? C25 C26 H26 120.7 . . ? C21 C26 H26 120.7 . . ? C28 C27 S8 121.57(17) . . ? C28 C27 S7 121.84(16) . . ? S8 C27 S7 116.58(13) . . ? C27 C28 S10 123.05(17) . . ? C27 C28 S9 121.41(17) . . ? S10 C28 S9 115.54(13) . . ? C30 C29 S11 123.09(18) . . ? C30 C29 S9 116.50(17) . . ? S11 C29 S9 120.34(13) . . ? C29 C30 S12 122.53(17) . . ? C29 C30 S10 116.44(17) . . ? S12 C30 S10 120.83(13) . . ? C32 C31 S11 108.9(2) . . ? C32 C31 H31A 109.9 . . ? S11 C31 H31A 109.9 . . ? C32 C31 H31B 109.9 . . ? S11 C31 H31B 109.9 . . ? H31A C31 H31B 108.3 . . ? C31 C32 C33 111.2(3) . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 S12 109.20(17) . . ? C35 C34 H34A 109.8 . . ? S12 C34 H34A 109.8 . . ? C35 C34 H34B 109.8 . . ? S12 C34 H34B 109.8 . . ? H34A C34 H34B 108.3 . . ? C34 C35 C36 110.0(2) . . ? C34 C35 H35A 109.7 . . ? C36 C35 H35A 109.7 . . ? C34 C35 H35B 109.7 . . ? C36 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C1 N1 C3 116.2(2) . . ? C2 N2 C4 116.1(2) . . ? C19 N3 C21 116.4(2) . . ? C20 N4 C22 116.2(2) . . ? C9 S1 C7 95.60(10) . . ? C6 S2 C9 95.88(10) . . ? C11 S3 C10 95.47(10) . . ? C12 S4 C10 95.59(10) . . ? C13B S5 C11 107.7(5) . . ? C11 S5 C13A 102.23(12) . . ? C12 S6 C16 100.06(12) . . ? C27 S7 C25 95.87(10) . . ? C27 S8 C24 95.75(10) . . ? C28 S9 C29 95.74(11) . . ? C28 S10 C30 95.71(11) . . ? C29 S11 C31 101.66(12) . . ? C30 S12 C34 102.25(11) . . ? I1 I2 I3 177.919(8) . . ? 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 C1 C2 N2 1.1(4) . . . . ? N1 C3 C4 N2 1.8(3) . . . . ? C8 C3 C4 N2 -177.8(2) . . . . ? N1 C3 C4 C5 -177.7(2) . . . . ? C8 C3 C4 C5 2.7(3) . . . . ? N2 C4 C5 C6 178.9(2) . . . . ? C3 C4 C5 C6 -1.7(3) . . . . ? C4 C5 C6 C7 -1.0(3) . . . . ? C4 C5 C6 S2 176.80(16) . . . . ? C5 C6 C7 C8 2.7(3) . . . . ? S2 C6 C7 C8 -175.21(16) . . . . ? C5 C6 C7 S1 -177.44(17) . . . . ? S2 C6 C7 S1 4.6(2) . . . . ? C6 C7 C8 C3 -1.6(3) . . . . ? S1 C7 C8 C3 178.53(16) . . . . ? N1 C3 C8 C7 179.3(2) . . . . ? C4 C3 C8 C7 -1.0(3) . . . . ? S2 C9 C10 S4 -2.4(3) . . . . ? S1 C9 C10 S4 176.86(12) . . . . ? S2 C9 C10 S3 179.28(12) . . . . ? S1 C9 C10 S3 -1.5(3) . . . . ? S5 C11 C12 S6 -2.3(3) . . . . ? S3 C11 C12 S6 -178.21(13) . . . . ? S5 C11 C12 S4 174.13(13) . . . . ? S3 C11 C12 S4 -1.7(3) . . . . ? S5 C13A C14A C15A 171.8(5) . . . . ? S5 C13B C14B C15B -175(2) . . . . ? S6 C16 C17 C18 171.0(2) . . . . ? N3 C19 C20 N4 0.3(4) . . . . ? N3 C21 C22 N4 0.5(3) . . . . ? C26 C21 C22 N4 -177.7(2) . . . . ? N3 C21 C22 C23 180.0(2) . . . . ? C26 C21 C22 C23 1.7(3) . . . . ? N4 C22 C23 C24 179.0(2) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C22 C23 C24 C25 -1.1(3) . . . . ? C22 C23 C24 S8 179.24(16) . . . . ? C23 C24 C25 C26 1.3(3) . . . . ? S8 C24 C25 C26 -178.97(17) . . . . ? C23 C24 C25 S7 -177.38(16) . . . . ? S8 C24 C25 S7 2.4(2) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? S7 C25 C26 C21 178.55(16) . . . . ? N3 C21 C26 C25 -179.8(2) . . . . ? C22 C21 C26 C25 -1.5(3) . . . . ? S8 C27 C28 S10 -3.7(3) . . . . ? S7 C27 C28 S10 176.80(12) . . . . ? S8 C27 C28 S9 176.67(12) . . . . ? S7 C27 C28 S9 -2.8(3) . . . . ? S11 C29 C30 S12 -2.5(3) . . . . ? S9 C29 C30 S12 174.41(13) . . . . ? S11 C29 C30 S10 -177.37(13) . . . . ? S9 C29 C30 S10 -0.5(3) . . . . ? S11 C31 C32 C33 176.7(2) . . . . ? S12 C34 C35 C36 -174.51(19) . . . . ? C2 C1 N1 C3 -0.4(3) . . . . ? C8 C3 N1 C1 178.6(2) . . . . ? C4 C3 N1 C1 -1.0(3) . . . . ? C1 C2 N2 C4 -0.4(3) . . . . ? C5 C4 N2 C2 178.4(2) . . . . ? C3 C4 N2 C2 -1.0(3) . . . . ? C20 C19 N3 C21 0.0(4) . . . . ? C26 C21 N3 C19 177.9(2) . . . . ? C22 C21 N3 C19 -0.4(3) . . . . ? C19 C20 N4 C22 -0.2(4) . . . . ? C23 C22 N4 C20 -179.6(2) . . . . ? C21 C22 N4 C20 -0.2(3) . . . . ? C10 C9 S1 C7 -177.42(19) . . . . ? S2 C9 S1 C7 1.88(14) . . . . ? C8 C7 S1 C9 176.02(19) . . . . ? C6 C7 S1 C9 -3.84(18) . . . . ? C5 C6 S2 C9 179.28(19) . . . . ? C7 C6 S2 C9 -2.82(18) . . . . ? C10 C9 S2 C6 179.44(19) . . . . ? S1 C9 S2 C6 0.13(14) . . . . ? C12 C11 S3 C10 -1.5(2) . . . . ? S5 C11 S3 C10 -177.59(14) . . . . ? C9 C10 S3 C11 -177.4(2) . . . . ? S4 C10 S3 C11 4.20(14) . . . . ? C11 C12 S4 C10 4.0(2) . . . . ? S6 C12 S4 C10 -179.19(14) . . . . ? C9 C10 S4 C12 176.62(19) . . . . ? S3 C10 S4 C12 -4.92(14) . . . . ? C14B C13B S5 C11 -83.7(9) . . . . ? C14B C13B S5 C13A 4.1(7) . . . . ? C12 C11 S5 C13B 160.9(5) . . . . ? S3 C11 S5 C13B -23.4(5) . . . . ? C12 C11 S5 C13A 120.2(2) . . . . ? S3 C11 S5 C13A -63.99(17) . . . . ? C14A C13A S5 C13B -0.7(7) . . . . ? C14A C13A S5 C11 102.4(2) . . . . ? C11 C12 S6 C16 -105.7(2) . . . . ? S4 C12 S6 C16 77.79(15) . . . . ? C17 C16 S6 C12 57.3(2) . . . . ? C28 C27 S7 C25 -179.17(19) . . . . ? S8 C27 S7 C25 1.30(14) . . . . ? C26 C25 S7 C27 179.22(19) . . . . ? C24 C25 S7 C27 -2.14(17) . . . . ? C28 C27 S8 C24 -179.81(19) . . . . ? S7 C27 S8 C24 -0.27(14) . . . . ? C23 C24 S8 C27 178.48(18) . . . . ? C25 C24 S8 C27 -1.24(18) . . . . ? C27 C28 S9 C29 176.86(19) . . . . ? S10 C28 S9 C29 -2.80(15) . . . . ? C30 C29 S9 C28 1.9(2) . . . . ? S11 C29 S9 C28 178.94(14) . . . . ? C27 C28 S10 C30 -177.1(2) . . . . ? S9 C28 S10 C30 2.60(15) . . . . ? C29 C30 S10 C28 -1.3(2) . . . . ? S12 C30 S10 C28 -176.24(14) . . . . ? C30 C29 S11 C31 174.2(2) . . . . ? S9 C29 S11 C31 -2.63(18) . . . . ? C32 C31 S11 C29 -173.6(2) . . . . ? C29 C30 S12 C34 154.1(2) . . . . ? S10 C30 S12 C34 -31.28(17) . . . . ? C35 C34 S12 C30 178.91(18) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 958951'