# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global #TrackingRef '- Li.cif' _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_address ; Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Universit Paris Descartes, UMR 8601 CNRS, 45 Rue des Saints P res, 75270 Paris cedex 06, France. ; _publ_contact_author_email yun.xu-li@parisdescartes _publ_contact_author_fax '+33 142868387' _publ_contact_author_phone '+33 142862175' _publ_contact_author_name 'Yun Li' _publ_contact_letter ; ? ; #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Unprecedented Ipso Aromatic Nucleophilic Substitution Upon Oxidative Decarboxylation of Tris-(p-carboxyltetrathiaaryl)methyl (TAM) Radicals: A New Access to Diversely Substituted TAM Radicals ; _publ_author_name 'Yun Li' data_Li _database_code_depnum_ccdc_archive 'CCDC 798319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common TAM(NO2)3 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H36 N3 O6 S12' _chemical_formula_weight 1003.53 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.7705(10) _cell_length_b 23.1060(10) _cell_length_c 16.2005(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.12(5) _cell_angle_gamma 90.00 _cell_volume 4406.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.92770 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5631 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 32.07 _reflns_number_total 5631 _reflns_number_gt 5465 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1073P)^2^+9.8204P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5631 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 2.219 _refine_ls_shift/su_mean 0.120 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 1.1236(4) 0.25337(19) 0.4340(3) 0.0219(10) Uani 1 1 d . . . C1A C 1.0630(4) 0.30445(18) 0.4649(3) 0.0207(10) Uani 1 1 d . . . C2A C 0.9761(4) 0.33099(19) 0.4179(3) 0.0195(10) Uani 1 1 d . . . C3A C 0.9221(4) 0.38200(19) 0.4449(3) 0.0198(10) Uani 1 1 d . . . C4A C 0.9579(4) 0.40555(19) 0.5213(3) 0.0237(11) Uani 1 1 d . . . C5A C 1.0401(4) 0.37950(19) 0.5713(3) 0.0204(10) Uani 1 1 d . . . C6A C 1.0917(4) 0.32872(18) 0.5422(3) 0.0186(10) Uani 1 1 d . . . N7A N 0.9042(3) 0.45798(16) 0.5495(2) 0.0256(9) Uani 1 1 d . . . O7A O 0.9550(3) 0.48821(15) 0.5995(2) 0.0375(9) Uani 1 1 d . . . O8A O 0.8084(3) 0.46977(15) 0.5220(2) 0.0373(9) Uani 1 1 d . . . S2A S 0.93356(10) 0.30603(5) 0.32090(7) 0.0253(3) Uani 1 1 d . . . S3A S 0.82029(10) 0.41108(5) 0.38012(7) 0.0265(3) Uani 1 1 d . . . C23A C 0.8744(4) 0.3755(2) 0.2873(3) 0.0271(11) Uani 1 1 d . . . C24A C 0.9659(4) 0.4126(2) 0.2468(3) 0.0334(12) Uani 1 1 d . . . H24A H 1.0270 0.4187 0.2851 0.040(4) Uiso 1 1 calc R . . H24B H 0.9340 0.4492 0.2310 0.040(4) Uiso 1 1 calc R . . H24C H 0.9942 0.3931 0.1987 0.040(4) Uiso 1 1 calc R . . C25A C 0.7741(4) 0.3644(2) 0.2284(3) 0.0337(12) Uani 1 1 d . . . H25A H 0.7182 0.3410 0.2558 0.040(4) Uiso 1 1 calc R . . H25B H 0.8008 0.3445 0.1802 0.040(4) Uiso 1 1 calc R . . H25C H 0.7408 0.4006 0.2125 0.040(4) Uiso 1 1 calc R . . S5A S 1.08522(10) 0.40393(5) 0.66793(7) 0.0266(3) Uani 1 1 d . . . S6A S 1.19386(9) 0.29833(5) 0.60796(7) 0.0222(3) Uani 1 1 d . . . C56A C 1.1348(4) 0.3319(2) 0.7006(3) 0.0248(10) Uani 1 1 d . . . C57A C 1.0343(4) 0.2968(2) 0.7326(3) 0.0277(11) Uani 1 1 d . . . H57A H 0.9777 0.2938 0.6900 0.040(4) Uiso 1 1 calc R . . H57B H 1.0024 0.3158 0.7799 0.040(4) Uiso 1 1 calc R . . H57C H 1.0597 0.2588 0.7479 0.040(4) Uiso 1 1 calc R . . C58A C 1.2269(4) 0.3385(2) 0.7643(3) 0.0317(12) Uani 1 1 d . . . H58A H 1.2884 0.3606 0.7415 0.040(4) Uiso 1 1 calc R . . H58B H 1.2540 0.3009 0.7803 0.040(4) Uiso 1 1 calc R . . H58C H 1.1971 0.3581 0.8118 0.040(4) Uiso 1 1 calc R . . C1B C 1.0586(4) 0.20401(18) 0.4032(3) 0.0180(10) Uani 1 1 d . . . C2B C 1.0862(4) 0.17907(19) 0.3260(3) 0.0197(10) Uani 1 1 d . . . C3B C 1.0328(4) 0.12862(18) 0.2985(3) 0.0204(10) Uani 1 1 d . . . C4B C 0.9532(4) 0.10194(18) 0.3510(3) 0.0198(10) Uani 1 1 d . . . C5B C 0.9227(4) 0.12560(18) 0.4277(3) 0.0197(10) Uani 1 1 d . . . C6B C 0.9735(4) 0.17755(18) 0.4519(3) 0.0189(10) Uani 1 1 d . . . N7B N 0.9004(3) 0.04859(15) 0.3239(2) 0.0245(9) Uani 1 1 d . . . O7B O 0.9461(3) 0.02103(14) 0.2680(2) 0.0334(8) Uani 1 1 d . . . O8B O 0.8122(3) 0.03303(14) 0.3584(2) 0.0363(9) Uani 1 1 d . . . S2B S 1.18949(9) 0.20797(5) 0.26017(7) 0.0220(3) Uani 1 1 d . . . S3B S 1.07288(10) 0.10484(5) 0.20039(7) 0.0240(3) Uani 1 1 d . . . C23B C 1.1271(4) 0.1757(2) 0.1681(3) 0.0242(10) Uani 1 1 d . . . C24B C 1.2190(4) 0.1667(2) 0.1028(3) 0.0330(12) Uani 1 1 d . . . H24D H 1.2785 0.1429 0.1251 0.040(4) Uiso 1 1 calc R . . H24E H 1.2497 0.2035 0.0868 0.040(4) Uiso 1 1 calc R . . H24F H 1.1865 0.1479 0.0554 0.040(4) Uiso 1 1 calc R . . C25B C 1.0295(4) 0.2133(2) 0.1360(3) 0.0269(11) Uani 1 1 d . . . H25D H 0.9737 0.2179 0.1786 0.040(4) Uiso 1 1 calc R . . H25E H 0.9952 0.1950 0.0890 0.040(4) Uiso 1 1 calc R . . H25F H 1.0584 0.2505 0.1203 0.040(4) Uiso 1 1 calc R . . S5B S 0.82692(10) 0.09508(5) 0.49692(7) 0.0255(3) Uani 1 1 d . . . S6B S 0.93230(10) 0.20436(5) 0.54845(7) 0.0239(3) Uani 1 1 d . . . C56B C 0.8795(4) 0.1349(2) 0.5868(3) 0.0264(11) Uani 1 1 d . . . C57B C 0.7800(4) 0.1456(2) 0.6454(3) 0.0318(12) Uani 1 1 d . . . H57D H 0.7219 0.1671 0.6172 0.040(4) Uiso 1 1 calc R . . H57E H 0.8060 0.1672 0.6924 0.040(4) Uiso 1 1 calc R . . H57F H 0.7496 0.1091 0.6634 0.040(4) Uiso 1 1 calc R . . C58B C 0.9737(4) 0.1007(2) 0.6294(3) 0.0350(12) Uani 1 1 d . . . H58D H 1.0351 0.0946 0.5914 0.040(4) Uiso 1 1 calc R . . H58E H 0.9446 0.0640 0.6472 0.040(4) Uiso 1 1 calc R . . H58F H 1.0009 0.1220 0.6764 0.040(4) Uiso 1 1 calc R . . C1C C 1.2467(4) 0.25107(18) 0.4349(2) 0.0196(10) Uani 1 1 d . . . C2C C 1.3054(4) 0.19814(18) 0.4517(3) 0.0188(10) Uani 1 1 d . . . C3C C 1.4233(4) 0.19546(18) 0.4510(3) 0.0202(10) Uani 1 1 d . . . C4C C 1.4846(4) 0.24568(19) 0.4327(3) 0.0214(10) Uani 1 1 d . . . C5C C 1.4318(4) 0.29872(18) 0.4164(3) 0.0204(10) Uani 1 1 d . . . C6C C 1.3131(4) 0.30142(19) 0.4178(3) 0.0188(10) Uani 1 1 d . . . N7C N 1.6071(3) 0.24332(15) 0.4325(2) 0.0224(8) Uani 1 1 d . . . O7C O 1.6605(3) 0.28085(14) 0.3939(2) 0.0321(8) Uani 1 1 d . . . O8C O 1.6543(3) 0.20384(15) 0.4713(2) 0.0347(8) Uani 1 1 d . . . S2C S 1.23803(10) 0.13491(5) 0.48564(7) 0.0253(3) Uani 1 1 d . . . S3C S 1.48449(10) 0.12823(5) 0.47562(8) 0.0256(3) Uani 1 1 d . . . C23C C 1.3537(4) 0.0871(2) 0.4561(3) 0.0266(11) Uani 1 1 d . . . C24C C 1.3490(4) 0.0348(2) 0.5130(4) 0.0383(13) Uani 1 1 d . . . H24G H 1.3546 0.0474 0.5693 0.035(4) Uiso 1 1 calc R . . H24H H 1.4111 0.0093 0.5007 0.035(4) Uiso 1 1 calc R . . H24I H 1.2785 0.0148 0.5049 0.035(4) Uiso 1 1 calc R . . C25C C 1.3447(5) 0.0706(2) 0.3659(3) 0.0367(12) Uani 1 1 d . . . H25G H 1.3477 0.1048 0.3325 0.035(4) Uiso 1 1 calc R . . H25H H 1.2741 0.0509 0.3563 0.035(4) Uiso 1 1 calc R . . H25I H 1.4067 0.0455 0.3516 0.035(4) Uiso 1 1 calc R . . S5C S 1.50300(9) 0.36247(5) 0.38993(7) 0.0241(3) Uani 1 1 d . . . S6C S 1.25574(9) 0.36805(5) 0.38794(7) 0.0217(3) Uani 1 1 d . . . C56C C 1.3818(4) 0.40958(19) 0.4146(3) 0.0220(10) Uani 1 1 d . . . C57C C 1.3891(4) 0.4627(2) 0.3607(3) 0.0287(11) Uani 1 1 d . . . H57G H 1.3879 0.4513 0.3037 0.035(4) Uiso 1 1 calc R . . H57H H 1.4584 0.4830 0.3723 0.035(4) Uiso 1 1 calc R . . H57I H 1.3255 0.4875 0.3718 0.035(4) Uiso 1 1 calc R . . C58C C 1.3829(4) 0.4240(2) 0.5066(3) 0.0266(11) Uani 1 1 d . . . H58G H 1.3780 0.3889 0.5381 0.035(4) Uiso 1 1 calc R . . H58H H 1.3192 0.4484 0.5194 0.035(4) Uiso 1 1 calc R . . H58I H 1.4521 0.4438 0.5202 0.035(4) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.024(2) 0.020(2) -0.003(2) 0.0034(18) 0.0003(19) C1A 0.020(2) 0.017(2) 0.026(2) 0.001(2) 0.0051(19) -0.0024(18) C2A 0.019(2) 0.022(2) 0.018(2) 0.002(2) -0.0006(17) -0.0033(18) C3A 0.020(2) 0.020(2) 0.020(2) 0.002(2) 0.0064(18) 0.0005(18) C4A 0.025(3) 0.020(2) 0.027(3) 0.000(2) 0.010(2) -0.0005(19) C5A 0.024(2) 0.020(2) 0.018(2) 0.000(2) 0.0025(18) -0.0025(19) C6A 0.019(2) 0.023(2) 0.015(2) 0.003(2) 0.0031(17) 0.0000(18) N7A 0.033(2) 0.0215(19) 0.022(2) -0.0013(18) 0.0076(17) 0.0027(17) O7A 0.052(2) 0.0253(18) 0.035(2) -0.0074(18) 0.0041(18) 0.0068(17) O8A 0.035(2) 0.038(2) 0.039(2) 0.0016(17) 0.0026(16) 0.0170(16) S2A 0.0276(7) 0.0282(7) 0.0201(6) -0.0020(5) -0.0034(5) 0.0012(5) S3A 0.0228(7) 0.0294(7) 0.0273(7) 0.0045(5) 0.0010(5) 0.0043(5) C23A 0.026(3) 0.031(3) 0.025(3) 0.007(2) -0.0009(19) 0.004(2) C24A 0.035(3) 0.036(3) 0.029(3) 0.005(2) 0.004(2) -0.005(2) C25A 0.032(3) 0.044(3) 0.025(3) 0.003(2) -0.012(2) 0.002(2) S5A 0.0340(7) 0.0268(7) 0.0191(6) -0.0058(5) 0.0017(5) 0.0021(5) S6A 0.0219(6) 0.0280(6) 0.0166(6) -0.0007(5) 0.0007(4) 0.0022(5) C56A 0.025(3) 0.027(3) 0.022(2) -0.004(2) 0.0016(19) 0.0035(19) C57A 0.028(3) 0.038(3) 0.017(2) 0.005(2) 0.0034(19) 0.002(2) C58A 0.031(3) 0.044(3) 0.021(2) -0.002(2) -0.008(2) 0.002(2) C1B 0.018(2) 0.020(2) 0.017(2) 0.0004(19) 0.0005(18) -0.0004(17) C2B 0.020(2) 0.022(2) 0.017(2) 0.005(2) 0.0015(18) -0.0004(18) C3B 0.021(2) 0.019(2) 0.022(2) 0.001(2) 0.0042(18) 0.0015(18) C4B 0.018(2) 0.017(2) 0.024(2) 0.002(2) -0.0033(18) -0.0040(17) C5B 0.022(2) 0.019(2) 0.018(2) 0.003(2) 0.0035(18) 0.0040(18) C6B 0.018(2) 0.023(2) 0.015(2) 0.000(2) 0.0020(17) 0.0043(18) N7B 0.030(2) 0.0205(19) 0.023(2) -0.0001(17) 0.0066(17) -0.0037(16) O7B 0.047(2) 0.0245(18) 0.0291(19) -0.0091(16) 0.0108(16) -0.0044(15) O8B 0.044(2) 0.0328(19) 0.0325(19) -0.0048(17) 0.0109(17) -0.0159(16) S2B 0.0215(6) 0.0269(6) 0.0176(6) -0.0030(5) 0.0046(5) -0.0038(4) S3B 0.0323(7) 0.0221(6) 0.0176(6) -0.0034(5) 0.0056(5) -0.0025(5) C23B 0.023(2) 0.025(2) 0.025(2) -0.004(2) 0.0065(19) -0.0072(19) C24B 0.035(3) 0.042(3) 0.022(3) -0.008(2) 0.014(2) -0.007(2) C25B 0.035(3) 0.027(3) 0.019(2) 0.008(2) 0.000(2) -0.005(2) S5B 0.0284(7) 0.0258(6) 0.0223(6) 0.0000(5) 0.0078(5) -0.0056(5) S6B 0.0278(7) 0.0265(6) 0.0175(6) -0.0027(5) 0.0076(5) -0.0033(5) C56B 0.028(3) 0.030(3) 0.020(2) 0.002(2) 0.008(2) -0.006(2) C57B 0.035(3) 0.038(3) 0.022(2) 0.002(2) 0.016(2) -0.001(2) C58B 0.036(3) 0.043(3) 0.026(3) 0.010(2) 0.004(2) 0.009(2) C1C 0.023(3) 0.023(2) 0.013(2) 0.0005(19) 0.0020(17) 0.0009(18) C2C 0.022(3) 0.019(2) 0.015(2) -0.0016(19) 0.0050(18) -0.0003(18) C3C 0.021(3) 0.021(2) 0.019(2) -0.005(2) 0.0016(18) -0.0011(18) C4C 0.021(3) 0.027(2) 0.016(2) -0.002(2) 0.0007(18) -0.0017(19) C5C 0.024(3) 0.022(2) 0.015(2) -0.0016(19) 0.0036(18) 0.0010(19) C6C 0.018(3) 0.025(2) 0.013(2) -0.0021(19) 0.0032(17) 0.0045(18) N7C 0.020(2) 0.0203(19) 0.0266(19) -0.0078(18) 0.0002(16) 0.0055(16) O7C 0.0234(18) 0.0319(19) 0.041(2) 0.0045(17) 0.0071(15) -0.0060(15) O8C 0.0218(19) 0.038(2) 0.044(2) -0.0010(18) -0.0027(16) 0.0047(15) S2C 0.0223(7) 0.0217(6) 0.0319(7) 0.0061(5) 0.0050(5) -0.0002(4) S3C 0.0208(7) 0.0232(6) 0.0327(7) 0.0040(5) 0.0005(5) 0.0028(4) C23C 0.024(3) 0.023(2) 0.033(3) 0.000(2) 0.001(2) 0.0009(19) C24C 0.029(3) 0.027(3) 0.059(4) 0.015(3) -0.001(2) 0.000(2) C25C 0.038(3) 0.031(3) 0.041(3) -0.004(3) 0.004(2) -0.004(2) S5C 0.0207(6) 0.0229(6) 0.0288(7) -0.0006(5) 0.0068(5) -0.0023(4) S6C 0.0211(6) 0.0212(6) 0.0228(6) 0.0031(5) 0.0022(5) -0.0006(4) C56C 0.023(2) 0.021(2) 0.022(2) 0.002(2) 0.0043(18) 0.0018(19) C57C 0.036(3) 0.024(2) 0.026(3) 0.004(2) 0.008(2) -0.002(2) C58C 0.034(3) 0.023(2) 0.023(2) -0.003(2) 0.003(2) 0.003(2) _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 C1C 1.450(7) . ? C1 C1B 1.460(6) . ? C1 C1A 1.468(6) . ? C1A C6A 1.413(6) . ? C1A C2A 1.414(6) . ? C2A C3A 1.409(6) . ? C2A S2A 1.745(4) . ? C3A C4A 1.416(7) . ? C3A S3A 1.727(5) . ? C4A C5A 1.398(7) . ? C4A N7A 1.441(6) . ? C5A C6A 1.403(6) . ? C5A S5A 1.745(4) . ? C6A S6A 1.751(4) . ? N7A O7A 1.224(5) . ? N7A O8A 1.242(5) . ? S2A C23A 1.832(5) . ? S3A C23A 1.829(5) . ? C23A C24A 1.526(7) . ? C23A C25A 1.538(7) . ? S5A C56A 1.841(5) . ? S6A C56A 1.829(4) . ? C56A C58A 1.502(6) . ? C56A C57A 1.526(7) . ? C1B C2B 1.416(6) . ? C1B C6B 1.416(6) . ? C2B C3B 1.397(6) . ? C2B S2B 1.751(4) . ? C3B C4B 1.408(6) . ? C3B S3B 1.748(4) . ? C4B C5B 1.406(6) . ? C4B N7B 1.448(6) . ? C5B C6B 1.396(6) . ? C5B S5B 1.741(4) . ? C6B S6B 1.752(4) . ? N7B O7B 1.231(5) . ? N7B O8B 1.234(5) . ? S2B C23B 1.821(5) . ? S3B C23B 1.833(5) . ? C23B C25B 1.530(7) . ? C23B C24B 1.530(6) . ? S5B C56B 1.829(5) . ? S6B C56B 1.830(5) . ? C56B C58B 1.525(7) . ? C56B C57B 1.530(6) . ? C1C C6C 1.429(6) . ? C1C C2C 1.431(6) . ? C2C C3C 1.389(7) . ? C2C S2C 1.752(4) . ? C3C C4C 1.399(6) . ? C3C S3C 1.758(4) . ? C4C C5C 1.399(6) . ? C4C N7C 1.442(6) . ? C5C C6C 1.400(7) . ? C5C S5C 1.749(4) . ? C6C S6C 1.749(4) . ? N7C O8C 1.238(5) . ? N7C O7C 1.241(5) . ? S2C C23C 1.818(5) . ? S3C C23C 1.837(5) . ? C23C C25C 1.514(7) . ? C23C C24C 1.519(7) . ? S5C C56C 1.839(4) . ? S6C C56C 1.819(5) . ? C56C C57C 1.508(7) . ? C56C C58C 1.527(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1C C1 C1B 119.8(4) . . ? C1C C1 C1A 120.8(4) . . ? C1B C1 C1A 119.4(4) . . ? C6A C1A C2A 118.5(4) . . ? C6A C1A C1 120.4(4) . . ? C2A C1A C1 121.1(4) . . ? C3A C2A C1A 121.4(4) . . ? C3A C2A S2A 115.3(3) . . ? C1A C2A S2A 123.2(3) . . ? C2A C3A C4A 117.4(4) . . ? C2A C3A S3A 116.7(3) . . ? C4A C3A S3A 125.9(3) . . ? C5A C4A C3A 123.1(4) . . ? C5A C4A N7A 118.8(4) . . ? C3A C4A N7A 118.1(4) . . ? C4A C5A C6A 117.7(4) . . ? C4A C5A S5A 126.1(3) . . ? C6A C5A S5A 116.2(3) . . ? C5A C6A C1A 121.8(4) . . ? C5A C6A S6A 115.3(3) . . ? C1A C6A S6A 122.9(3) . . ? O7A N7A O8A 123.6(4) . . ? O7A N7A C4A 118.4(4) . . ? O8A N7A C4A 118.0(4) . . ? C2A S2A C23A 94.9(2) . . ? C3A S3A C23A 94.7(2) . . ? C24A C23A C25A 111.6(4) . . ? C24A C23A S3A 110.4(3) . . ? C25A C23A S3A 108.5(3) . . ? C24A C23A S2A 110.6(3) . . ? C25A C23A S2A 109.2(3) . . ? S3A C23A S2A 106.4(2) . . ? C5A S5A C56A 93.5(2) . . ? C6A S6A C56A 93.9(2) . . ? C58A C56A C57A 112.3(4) . . ? C58A C56A S6A 109.4(3) . . ? C57A C56A S6A 110.4(3) . . ? C58A C56A S5A 109.5(3) . . ? C57A C56A S5A 109.4(3) . . ? S6A C56A S5A 105.6(2) . . ? C2B C1B C6B 118.7(4) . . ? C2B C1B C1 119.9(4) . . ? C6B C1B C1 121.2(4) . . ? C3B C2B C1B 121.1(4) . . ? C3B C2B S2B 115.9(3) . . ? C1B C2B S2B 122.9(3) . . ? C2B C3B C4B 118.2(4) . . ? C2B C3B S3B 115.4(3) . . ? C4B C3B S3B 126.3(3) . . ? C5B C4B C3B 122.4(4) . . ? C5B C4B N7B 119.3(4) . . ? C3B C4B N7B 118.4(4) . . ? C6B C5B C4B 118.2(4) . . ? C6B C5B S5B 116.4(3) . . ? C4B C5B S5B 125.4(3) . . ? C5B C6B C1B 121.2(4) . . ? C5B C6B S6B 115.8(3) . . ? C1B C6B S6B 122.8(3) . . ? O7B N7B O8B 123.5(4) . . ? O7B N7B C4B 118.4(4) . . ? O8B N7B C4B 118.1(4) . . ? C2B S2B C23B 93.6(2) . . ? C3B S3B C23B 94.2(2) . . ? C25B C23B C24B 111.9(4) . . ? C25B C23B S2B 110.3(3) . . ? C24B C23B S2B 109.7(3) . . ? C25B C23B S3B 110.1(3) . . ? C24B C23B S3B 108.9(3) . . ? S2B C23B S3B 105.8(2) . . ? C5B S5B C56B 95.2(2) . . ? C6B S6B C56B 95.0(2) . . ? C58B C56B C57B 111.1(4) . . ? C58B C56B S5B 110.1(3) . . ? C57B C56B S5B 108.5(3) . . ? C58B C56B S6B 111.2(3) . . ? C57B C56B S6B 109.3(3) . . ? S5B C56B S6B 106.6(2) . . ? C6C C1C C2C 118.0(4) . . ? C6C C1C C1 121.0(4) . . ? C2C C1C C1 121.0(4) . . ? C3C C2C C1C 121.2(4) . . ? C3C C2C S2C 114.7(3) . . ? C1C C2C S2C 123.6(3) . . ? C2C C3C C4C 118.7(4) . . ? C2C C3C S3C 116.5(3) . . ? C4C C3C S3C 124.7(3) . . ? C5C C4C C3C 122.5(4) . . ? C5C C4C N7C 118.5(4) . . ? C3C C4C N7C 119.0(4) . . ? C4C C5C C6C 118.7(4) . . ? C4C C5C S5C 124.8(3) . . ? C6C C5C S5C 116.4(3) . . ? C5C C6C C1C 120.9(4) . . ? C5C C6C S6C 114.8(3) . . ? C1C C6C S6C 124.0(3) . . ? O8C N7C O7C 122.9(4) . . ? O8C N7C C4C 118.3(4) . . ? O7C N7C C4C 118.8(4) . . ? C2C S2C C23C 94.9(2) . . ? C3C S3C C23C 94.3(2) . . ? C25C C23C C24C 112.5(4) . . ? C25C C23C S2C 110.9(3) . . ? C24C C23C S2C 107.2(3) . . ? C25C C23C S3C 110.7(3) . . ? C24C C23C S3C 109.8(3) . . ? S2C C23C S3C 105.5(2) . . ? C5C S5C C56C 94.2(2) . . ? C6C S6C C56C 94.8(2) . . ? C57C C56C C58C 112.8(4) . . ? C57C C56C S6C 109.8(3) . . ? C58C C56C S6C 110.6(3) . . ? C57C C56C S5C 108.1(3) . . ? C58C C56C S5C 109.7(3) . . ? S6C C56C S5C 105.6(2) . . ? _diffrn_measured_fraction_theta_max 0.813 _diffrn_reflns_theta_full 32.07 _diffrn_measured_fraction_theta_full 0.813 _refine_diff_density_max 0.492 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.113