# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 ####################################################################### # # 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_ccd751 _database_code_depnum_ccdc_archive 'CCDC 284569' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [N,N'-dimethyldihdrophenazine][N,N'-diethylviologen] ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 F12 N6 O8 S4' _chemical_formula_weight 984.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.490(5) _cell_length_b 12.820(5) _cell_length_c 13.993(6) _cell_angle_alpha 71.643(6) _cell_angle_beta 72.240(7) _cell_angle_gamma 82.390(8) _cell_volume 2023.5(14) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_crystal_preparation ; crystallized from ionic liquid comprised of N,N'-dimethyldihdrophenazine and N,N'-diethylviologen ; _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.8623 _exptl_absorpt_correction_T_max 0.9661 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; Decay of reflection intensity was monitored via analysis of redundant frames ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4/CCD' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 12935 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.39 _reflns_number_total 6768 _reflns_number_gt 5698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (v. 4.202, Siemens 1996)' _computing_cell_refinement 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_data_reduction 'Bruker SAINT (v. 5.00, Bruker 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHEXTL (v. 5.10)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0666P)^2^+0.0000P] 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 6768 _refine_ls_number_parameters 559 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1609 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 1.650 _refine_ls_restrained_S_all 1.650 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.78651(8) 0.78396(7) 0.28790(7) 0.0421(2) Uani 1 1 d . . . S2 S 0.95795(8) 0.62008(7) 0.28375(7) 0.0407(2) Uani 1 1 d . . . S3 S 0.49346(8) 0.21025(8) 0.06257(7) 0.0432(3) Uani 1 1 d . . . S4 S 0.42586(8) 0.27176(7) 0.24765(7) 0.0376(2) Uani 1 1 d . . . F1 F 0.7486(2) 0.78792(19) 0.48149(17) 0.0577(6) Uani 1 1 d . . . F2 F 0.6006(2) 0.7748(3) 0.4386(2) 0.0823(9) Uani 1 1 d . . . F3 F 0.7132(2) 0.63461(19) 0.46813(18) 0.0637(7) Uani 1 1 d . . . F4 F 0.9878(3) 0.6991(3) 0.0813(2) 0.0888(9) Uani 1 1 d . . . F5 F 1.1271(2) 0.7178(3) 0.1313(2) 0.0893(9) Uani 1 1 d . . . F6 F 1.0941(3) 0.5591(3) 0.1275(3) 0.1011(11) Uani 1 1 d . . . F7 F 0.6999(2) 0.1335(2) 0.0558(2) 0.0663(7) Uani 1 1 d . . . F8 F 0.5745(2) 0.04715(19) 0.19151(18) 0.0644(7) Uani 1 1 d . . . F9 F 0.5933(2) 0.0244(2) 0.0411(2) 0.0769(8) Uani 1 1 d . . . F10 F 0.2490(2) 0.3509(3) 0.1824(2) 0.0843(9) Uani 1 1 d . . . F11 F 0.3585(3) 0.4736(2) 0.1653(2) 0.0886(9) Uani 1 1 d . . . F12 F 0.2535(2) 0.3930(2) 0.3163(2) 0.0788(8) Uani 1 1 d . . . O1 O 0.7866(2) 0.9008(2) 0.2616(2) 0.0570(7) Uani 1 1 d . . . O2 O 0.7311(2) 0.7356(2) 0.2386(2) 0.0588(8) Uani 1 1 d . . . O3 O 0.8792(2) 0.5455(2) 0.2901(2) 0.0558(7) Uani 1 1 d . . . O4 O 1.0356(3) 0.5809(2) 0.3444(2) 0.0599(8) Uani 1 1 d . . . O5 O 0.3894(2) 0.1575(3) 0.0922(2) 0.0563(7) Uani 1 1 d . . . O6 O 0.5402(3) 0.2685(3) -0.0452(2) 0.0692(9) Uani 1 1 d . . . O7 O 0.4857(2) 0.3104(2) 0.3011(2) 0.0534(7) Uani 1 1 d . . . O8 O 0.3664(2) 0.1730(2) 0.30182(18) 0.0454(6) Uani 1 1 d . . . N1 N 0.8952(2) 0.2343(2) 0.4589(2) 0.0307(6) Uani 1 1 d . . . N2 N 0.7221(2) 0.1223(2) 0.4611(2) 0.0335(6) Uani 1 1 d . . . N3 N 0.9091(3) 0.7381(2) 0.2916(2) 0.0418(7) Uani 1 1 d . . . N4 N 0.5028(3) 0.2816(2) 0.1329(2) 0.0463(8) Uani 1 1 d . . . N5 N 0.1105(3) 0.0224(3) 0.2311(2) 0.0450(8) Uani 1 1 d . . . N6 N 0.6124(2) 0.5162(2) 0.2331(2) 0.0351(6) Uani 1 1 d . . . C1 C 0.9902(3) 0.2885(3) 0.4596(3) 0.0383(8) Uani 1 1 d . . . H1A H 1.0476 0.2964 0.3942 0.057 Uiso 1 1 calc R . . H1B H 1.0198 0.2451 0.5162 0.057 Uiso 1 1 calc R . . H1C H 0.9657 0.3598 0.4688 0.057 Uiso 1 1 calc R . . C2 C 0.6361(3) 0.0547(3) 0.4631(3) 0.0430(9) Uani 1 1 d . . . H2A H 0.5984 0.0173 0.5345 0.064 Uiso 1 1 calc R . . H2B H 0.6707 0.0017 0.4263 0.064 Uiso 1 1 calc R . . H2C H 0.5826 0.1006 0.4299 0.064 Uiso 1 1 calc R . . C3 C 0.8009(3) 0.2146(2) 0.5486(2) 0.0294(7) Uani 1 1 d . . . C4 C 0.7952(3) 0.2463(3) 0.6365(3) 0.0370(8) Uani 1 1 d . . . H4 H 0.8516 0.2880 0.6348 0.044 Uiso 1 1 calc R . . C5 C 0.7059(3) 0.2165(3) 0.7270(3) 0.0429(9) Uani 1 1 d . . . H5 H 0.7045 0.2358 0.7861 0.051 Uiso 1 1 calc R . . C6 C 0.6202(3) 0.1588(3) 0.7292(3) 0.0448(9) Uani 1 1 d . . . H6 H 0.5606 0.1390 0.7897 0.054 Uiso 1 1 calc R . . C7 C 0.6224(3) 0.1295(3) 0.6400(3) 0.0381(8) Uani 1 1 d . . . H7 H 0.5630 0.0920 0.6412 0.046 Uiso 1 1 calc R . . C8 C 0.7123(3) 0.1558(2) 0.5500(2) 0.0313(7) Uani 1 1 d . . . C9 C 0.7877(3) 0.1844(2) 0.3634(3) 0.0316(7) Uani 1 1 d . . . C10 C 0.7701(3) 0.1887(3) 0.2688(3) 0.0393(8) Uani 1 1 d . . . H10 H 0.7101 0.1528 0.2688 0.047 Uiso 1 1 calc R . . C11 C 0.8416(3) 0.2462(3) 0.1740(3) 0.0461(9) Uani 1 1 d . . . H11 H 0.8301 0.2468 0.1112 0.055 Uiso 1 1 calc R . . C12 C 0.9288(3) 0.3021(3) 0.1723(3) 0.0442(9) Uani 1 1 d . . . H12 H 0.9763 0.3405 0.1087 0.053 Uiso 1 1 calc R . . C13 C 0.9459(3) 0.3011(3) 0.2665(3) 0.0362(8) Uani 1 1 d . . . H13 H 1.0041 0.3404 0.2652 0.043 Uiso 1 1 calc R . . C14 C 0.8777(3) 0.2425(2) 0.3620(2) 0.0298(7) Uani 1 1 d . . . C15 C 0.5245(3) 0.5038(2) 0.4435(2) 0.0308(7) Uani 1 1 d . . . C16 C 0.6200(3) 0.4437(3) 0.4081(3) 0.0398(8) Uani 1 1 d . . . H16 H 0.6562 0.3975 0.4558 0.048 Uiso 1 1 calc R . . C17 C 0.6627(3) 0.4508(3) 0.3037(3) 0.0406(8) Uani 1 1 d . . . H17 H 0.7275 0.4097 0.2816 0.049 Uiso 1 1 calc R . . C19 C 0.5211(3) 0.5772(3) 0.2648(3) 0.0494(10) Uani 1 1 d . . . H19 H 0.4877 0.6243 0.2154 0.059 Uiso 1 1 calc R . . C20 C 0.4759(3) 0.5722(3) 0.3676(3) 0.0509(10) Uani 1 1 d . . . H20 H 0.4117 0.6150 0.3873 0.061 Uiso 1 1 calc R . . C21 C 0.6585(3) 0.5186(3) 0.1208(3) 0.0459(9) Uani 1 1 d . . . H21A H 0.6762 0.4441 0.1163 0.055 Uiso 1 1 calc R . . H21B H 0.6020 0.5509 0.0841 0.055 Uiso 1 1 calc R . . C22 C 0.7617(4) 0.5837(4) 0.0698(3) 0.0679(13) Uani 1 1 d . . . H22A H 0.7898 0.5841 -0.0022 0.102 Uiso 1 1 calc R . . H22B H 0.8179 0.5513 0.1055 0.102 Uiso 1 1 calc R . . H22C H 0.7439 0.6579 0.0733 0.102 Uiso 1 1 calc R . . C23 C 0.0231(3) 0.0061(2) 0.4430(2) 0.0276(7) Uani 1 1 d . . . C24 C -0.0368(3) -0.0257(3) 0.3876(3) 0.0349(7) Uani 1 1 d . . . H24 H -0.1083 -0.0529 0.4220 0.042 Uiso 1 1 calc R . . C25 C 0.0084(3) -0.0171(3) 0.2837(3) 0.0418(9) Uani 1 1 d . . . H25 H -0.0327 -0.0393 0.2486 0.050 Uiso 1 1 calc R . . C27 C 0.1694(3) 0.0577(3) 0.2803(3) 0.0376(8) Uani 1 1 d . . . H27 H 0.2393 0.0873 0.2429 0.045 Uiso 1 1 calc R . . C28 C 0.1278(3) 0.0504(3) 0.3843(2) 0.0317(7) Uani 1 1 d . . . H28 H 0.1698 0.0753 0.4167 0.038 Uiso 1 1 calc R . . C29 C 0.1631(4) 0.0242(5) 0.1194(3) 0.0803(16) Uani 1 1 d . . . H29A H 0.2359 0.0567 0.0964 0.096 Uiso 1 1 calc R . . H29B H 0.1767 -0.0513 0.1172 0.096 Uiso 1 1 calc R . . C30 C 0.1081(8) 0.0762(10) 0.0514(4) 0.257(8) Uani 1 1 d . . . H30A H 0.1501 0.0699 -0.0167 0.385 Uiso 1 1 calc R . . H30B H 0.0975 0.1524 0.0491 0.385 Uiso 1 1 calc R . . H30C H 0.0361 0.0446 0.0716 0.385 Uiso 1 1 calc R . . C31 C 0.7073(3) 0.7424(3) 0.4271(3) 0.0467(9) Uani 1 1 d . . . C32 C 1.0477(4) 0.6512(4) 0.1493(3) 0.0576(11) Uani 1 1 d . . . C33 C 0.5969(3) 0.0976(3) 0.0895(3) 0.0464(9) Uani 1 1 d . . . C34 C 0.3158(4) 0.3787(3) 0.2263(3) 0.0507(10) 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 S1 0.0425(6) 0.0430(5) 0.0443(5) -0.0164(4) -0.0137(4) -0.0015(4) S2 0.0435(6) 0.0362(5) 0.0446(5) -0.0157(4) -0.0105(4) -0.0032(4) S3 0.0380(6) 0.0576(6) 0.0287(4) -0.0103(4) -0.0041(4) -0.0024(5) S4 0.0357(5) 0.0394(5) 0.0379(5) -0.0126(4) -0.0073(4) -0.0059(4) F1 0.0656(16) 0.0661(14) 0.0506(13) -0.0313(11) -0.0114(12) -0.0095(12) F2 0.0387(15) 0.126(2) 0.0836(19) -0.0480(18) -0.0074(14) 0.0099(16) F3 0.0762(18) 0.0555(14) 0.0526(13) -0.0160(11) 0.0007(13) -0.0235(13) F4 0.102(2) 0.115(2) 0.0426(14) -0.0218(15) -0.0136(15) -0.0015(19) F5 0.0601(19) 0.101(2) 0.094(2) -0.0303(17) 0.0112(16) -0.0318(18) F6 0.103(2) 0.086(2) 0.102(2) -0.0595(18) 0.0140(19) 0.0126(18) F7 0.0344(14) 0.0799(17) 0.0801(17) -0.0256(14) -0.0049(12) -0.0077(13) F8 0.0630(17) 0.0603(15) 0.0546(14) -0.0022(11) -0.0118(12) 0.0027(12) F9 0.0688(18) 0.0815(18) 0.095(2) -0.0573(16) -0.0114(15) -0.0030(14) F10 0.0658(18) 0.109(2) 0.092(2) -0.0349(17) -0.0445(17) 0.0165(16) F11 0.078(2) 0.0553(16) 0.101(2) 0.0022(15) -0.0109(17) 0.0061(14) F12 0.0688(18) 0.0901(19) 0.0703(17) -0.0361(15) -0.0081(14) 0.0255(15) O1 0.0583(19) 0.0432(15) 0.0677(18) -0.0101(13) -0.0234(15) 0.0035(13) O2 0.0562(18) 0.0727(19) 0.0595(17) -0.0300(15) -0.0240(15) 0.0022(15) O3 0.0571(18) 0.0435(14) 0.0723(19) -0.0251(13) -0.0146(15) -0.0089(13) O4 0.066(2) 0.0476(15) 0.077(2) -0.0188(14) -0.0374(17) 0.0031(14) O5 0.0361(16) 0.094(2) 0.0450(15) -0.0321(15) -0.0056(13) -0.0080(15) O6 0.068(2) 0.088(2) 0.0300(14) -0.0019(14) -0.0028(14) 0.0042(17) O7 0.0495(17) 0.0588(16) 0.0617(17) -0.0256(14) -0.0195(14) -0.0059(14) O8 0.0516(17) 0.0481(14) 0.0335(13) -0.0107(11) -0.0035(12) -0.0148(12) N1 0.0244(15) 0.0304(13) 0.0373(15) -0.0073(11) -0.0100(12) -0.0046(12) N2 0.0299(16) 0.0331(14) 0.0375(15) -0.0093(12) -0.0084(13) -0.0058(12) N3 0.0405(18) 0.0389(16) 0.0490(18) -0.0199(14) -0.0085(15) -0.0041(14) N4 0.0417(19) 0.0433(17) 0.0446(18) -0.0101(14) 0.0031(15) -0.0124(15) N5 0.040(2) 0.0608(19) 0.0339(16) -0.0166(14) -0.0029(15) -0.0122(16) N6 0.0371(17) 0.0337(14) 0.0336(15) -0.0091(12) -0.0096(13) -0.0002(13) C1 0.035(2) 0.0382(18) 0.0419(19) -0.0105(15) -0.0096(17) -0.0070(16) C2 0.040(2) 0.0413(19) 0.048(2) -0.0124(16) -0.0095(18) -0.0128(17) C3 0.0242(18) 0.0242(15) 0.0361(17) -0.0038(13) -0.0088(15) 0.0006(13) C4 0.032(2) 0.0353(17) 0.044(2) -0.0122(15) -0.0121(17) 0.0027(15) C5 0.043(2) 0.048(2) 0.038(2) -0.0142(16) -0.0132(18) 0.0070(18) C6 0.039(2) 0.046(2) 0.0363(19) -0.0059(16) -0.0025(17) 0.0056(18) C7 0.031(2) 0.0365(18) 0.0400(19) -0.0045(15) -0.0058(16) -0.0031(15) C8 0.0273(19) 0.0257(15) 0.0365(18) -0.0036(13) -0.0106(15) 0.0045(14) C9 0.0298(19) 0.0275(15) 0.0371(18) -0.0104(13) -0.0096(15) 0.0036(14) C10 0.040(2) 0.0390(18) 0.041(2) -0.0144(15) -0.0110(17) -0.0014(16) C11 0.051(3) 0.052(2) 0.0353(19) -0.0168(17) -0.0116(18) 0.0045(19) C12 0.045(2) 0.046(2) 0.0354(19) -0.0115(16) -0.0021(17) -0.0016(18) C13 0.032(2) 0.0311(17) 0.0410(19) -0.0090(14) -0.0044(16) -0.0035(15) C14 0.0272(18) 0.0246(15) 0.0361(18) -0.0092(13) -0.0080(15) 0.0033(14) C15 0.0310(19) 0.0262(15) 0.0333(17) -0.0039(13) -0.0093(15) -0.0058(14) C16 0.042(2) 0.0387(18) 0.0375(19) -0.0083(15) -0.0174(17) 0.0112(17) C17 0.043(2) 0.0388(18) 0.043(2) -0.0161(16) -0.0164(17) 0.0119(16) C19 0.046(2) 0.055(2) 0.037(2) -0.0036(17) -0.0158(18) 0.0167(19) C20 0.046(2) 0.057(2) 0.038(2) -0.0103(17) -0.0104(18) 0.024(2) C21 0.050(2) 0.050(2) 0.040(2) -0.0146(17) -0.0164(19) 0.0028(19) C22 0.073(3) 0.087(3) 0.040(2) -0.017(2) -0.003(2) -0.027(3) C23 0.0227(18) 0.0219(14) 0.0338(16) -0.0052(12) -0.0051(14) 0.0002(13) C24 0.032(2) 0.0357(17) 0.0350(18) -0.0089(14) -0.0081(15) -0.0026(15) C25 0.036(2) 0.054(2) 0.0383(19) -0.0163(17) -0.0079(18) -0.0114(18) C27 0.0290(19) 0.0403(18) 0.0389(19) -0.0092(15) -0.0030(16) -0.0073(16) C28 0.030(2) 0.0329(16) 0.0322(17) -0.0070(13) -0.0110(15) -0.0010(15) C29 0.066(3) 0.138(5) 0.039(2) -0.039(3) 0.009(2) -0.035(3) C30 0.188(9) 0.461(18) 0.033(3) -0.046(6) -0.029(4) 0.219(11) C31 0.040(2) 0.052(2) 0.053(2) -0.0254(19) -0.0103(19) -0.0013(18) C32 0.053(3) 0.059(3) 0.058(3) -0.024(2) -0.008(2) 0.002(2) C33 0.041(2) 0.053(2) 0.045(2) -0.0194(18) -0.0041(18) -0.0050(19) C34 0.045(2) 0.055(2) 0.046(2) -0.0094(19) -0.008(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 S1 O2 1.420(3) . ? S1 O1 1.426(3) . ? S1 N3 1.576(3) . ? S1 C31 1.835(4) . ? S2 O4 1.421(3) . ? S2 O3 1.426(3) . ? S2 N3 1.578(3) . ? S2 C32 1.821(4) . ? S3 O6 1.429(3) . ? S3 O5 1.431(3) . ? S3 N4 1.576(3) . ? S3 C33 1.832(4) . ? S4 O8 1.425(3) . ? S4 O7 1.427(3) . ? S4 N4 1.576(3) . ? S4 C34 1.830(4) . ? F1 C31 1.335(4) . ? F2 C31 1.319(4) . ? F3 C31 1.321(4) . ? F4 C32 1.336(5) . ? F5 C32 1.309(5) . ? F6 C32 1.326(5) . ? F7 C33 1.319(5) . ? F8 C33 1.326(4) . ? F9 C33 1.330(4) . ? F10 C34 1.315(5) . ? F11 C34 1.317(5) . ? F12 C34 1.317(5) . ? N1 C14 1.407(4) . ? N1 C3 1.416(4) . ? N1 C1 1.455(4) . ? N2 C9 1.406(4) . ? N2 C8 1.406(4) . ? N2 C2 1.455(4) . ? N5 C25 1.337(5) . ? N5 C27 1.346(4) . ? N5 C29 1.494(5) . ? N6 C19 1.334(4) . ? N6 C17 1.338(4) . ? N6 C21 1.491(4) . ? C3 C4 1.392(5) . ? C3 C8 1.412(4) . ? C4 C5 1.393(5) . ? C5 C6 1.367(5) . ? C6 C7 1.404(5) . ? C7 C8 1.389(5) . ? C9 C10 1.391(5) . ? C9 C14 1.421(4) . ? C10 C11 1.392(5) . ? C11 C12 1.372(5) . ? C12 C13 1.394(5) . ? C13 C14 1.385(5) . ? C15 C16 1.378(5) . ? C15 C20 1.389(5) . ? C15 C15 1.489(6) 2_666 ? C16 C17 1.371(5) . ? C19 C20 1.359(5) . ? C21 C22 1.489(6) . ? C23 C28 1.397(5) . ? C23 C24 1.401(4) . ? C23 C23 1.486(6) 2_556 ? C24 C25 1.363(5) . ? C27 C28 1.365(5) . ? C29 C30 1.304(8) . ? 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 O2 S1 O1 119.30(17) . . ? O2 S1 N3 117.06(16) . . ? O1 S1 N3 107.45(17) . . ? O2 S1 C31 104.85(18) . . ? O1 S1 C31 103.68(17) . . ? N3 S1 C31 102.12(17) . . ? O4 S2 O3 118.13(17) . . ? O4 S2 N3 109.83(16) . . ? O3 S2 N3 116.30(17) . . ? O4 S2 C32 103.3(2) . . ? O3 S2 C32 104.97(19) . . ? N3 S2 C32 101.84(18) . . ? O6 S3 O5 118.65(18) . . ? O6 S3 N4 108.92(19) . . ? O5 S3 N4 116.24(16) . . ? O6 S3 C33 103.92(18) . . ? O5 S3 C33 104.74(19) . . ? N4 S3 C33 102.09(17) . . ? O8 S4 O7 118.36(16) . . ? O8 S4 N4 116.70(15) . . ? O7 S4 N4 108.46(18) . . ? O8 S4 C34 104.40(18) . . ? O7 S4 C34 104.02(18) . . ? N4 S4 C34 102.74(17) . . ? C14 N1 C3 117.7(3) . . ? C14 N1 C1 118.9(3) . . ? C3 N1 C1 118.5(3) . . ? C9 N2 C8 118.3(3) . . ? C9 N2 C2 118.7(3) . . ? C8 N2 C2 119.1(3) . . ? S1 N3 S2 124.75(19) . . ? S4 N4 S3 125.0(2) . . ? C25 N5 C27 119.8(3) . . ? C25 N5 C29 121.3(3) . . ? C27 N5 C29 118.9(3) . . ? C19 N6 C17 119.3(3) . . ? C19 N6 C21 121.2(3) . . ? C17 N6 C21 119.4(3) . . ? C4 C3 C8 119.3(3) . . ? C4 C3 N1 122.5(3) . . ? C8 C3 N1 118.2(3) . . ? C3 C4 C5 120.8(3) . . ? C6 C5 C4 120.1(3) . . ? C5 C6 C7 119.9(3) . . ? C8 C7 C6 120.9(3) . . ? C7 C8 N2 123.1(3) . . ? C7 C8 C3 118.9(3) . . ? N2 C8 C3 117.9(3) . . ? C10 C9 N2 122.9(3) . . ? C10 C9 C14 119.0(3) . . ? N2 C9 C14 118.1(3) . . ? C9 C10 C11 120.6(3) . . ? C12 C11 C10 120.6(3) . . ? C11 C12 C13 119.6(3) . . ? C14 C13 C12 121.1(3) . . ? C13 C14 N1 123.2(3) . . ? C13 C14 C9 119.1(3) . . ? N1 C14 C9 117.7(3) . . ? C16 C15 C20 116.3(3) . . ? C16 C15 C15 122.1(3) . 2_666 ? C20 C15 C15 121.6(4) . 2_666 ? C17 C16 C15 121.1(3) . . ? N6 C17 C16 120.8(3) . . ? N6 C19 C20 121.6(3) . . ? C19 C20 C15 120.8(3) . . ? C22 C21 N6 111.0(3) . . ? C28 C23 C24 115.9(3) . . ? C28 C23 C23 122.6(4) . 2_556 ? C24 C23 C23 121.5(4) . 2_556 ? C25 C24 C23 120.8(3) . . ? N5 C25 C24 121.5(3) . . ? N5 C27 C28 120.8(3) . . ? C27 C28 C23 121.2(3) . . ? C30 C29 N5 117.8(5) . . ? F2 C31 F3 108.6(3) . . ? F2 C31 F1 108.3(3) . . ? F3 C31 F1 107.8(3) . . ? F2 C31 S1 110.3(3) . . ? F3 C31 S1 111.4(2) . . ? F1 C31 S1 110.5(3) . . ? F5 C32 F6 109.2(4) . . ? F5 C32 F4 107.2(4) . . ? F6 C32 F4 106.7(4) . . ? F5 C32 S2 112.4(3) . . ? F6 C32 S2 110.2(3) . . ? F4 C32 S2 110.9(3) . . ? F7 C33 F8 108.4(3) . . ? F7 C33 F9 108.3(3) . . ? F8 C33 F9 108.3(3) . . ? F7 C33 S3 111.4(3) . . ? F8 C33 S3 110.7(3) . . ? F9 C33 S3 109.6(3) . . ? F10 C34 F11 108.0(3) . . ? F10 C34 F12 107.6(4) . . ? F11 C34 F12 108.1(4) . . ? F10 C34 S4 110.9(3) . . ? F11 C34 S4 111.7(3) . . ? F12 C34 S4 110.4(3) . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.676 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.059