# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _audit_creation_date 10-05-02 _journal_coden_Cambridge 440 _publ_contact_author_name 'Prof Pierre Braunstein' _publ_contact_author_address ; Laboratoire de Chimie de Coordination, UMR 7513 CNRS Universite Louis Pasteur 4, rue Blaise Pascal Strasbourg F-67070 FRANCE ; _publ_contact_author_phone 0390241308 _publ_contact_author_fax 0390241322 _publ_contact_author_email braunst@chimie.u-strasbg.fr _publ_requested_journal 'New J. Chem' _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; One-electron oxidation-induced dimerisation of a 2,5-diamino-1,4-benzoquinonediimine: a chemical and electrochemical investigation ; loop_ _publ_author_name 'Pierre Braunstein' 'Jean-Paul Collin' 'Abdellatif Messaoudi' 'Olivier Siri' 'Jean-philippe Taquet' _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. A.L. Spek, PLATON 98, Utrecht University, The Netherland, 1998. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. University of Gottingen. Germany. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_shelxl _database_code_depnum_ccdc_archive 'CCDC 250423' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H96 N8, 2(C F3 O3 S), 2(H2O)' _chemical_formula_sum 'C54 H100 F6 N8 O8 S2' _chemical_formula_weight 1167.54 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 12.3030(3) _cell_length_b 17.0200(4) _cell_length_c 16.8770(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.6510(11) _cell_angle_gamma 90.00 _cell_volume 3510.21(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 29923 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 32.032 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12183 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1220 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 32.06 _reflns_number_total 12182 _reflns_number_gt 7021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _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^)+(0.2000P)^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 12182 _refine_ls_number_parameters 367 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2167 _refine_ls_R_factor_gt 0.1451 _refine_ls_wR_factor_ref 0.4187 _refine_ls_wR_factor_gt 0.3820 _refine_ls_goodness_of_fit_ref 1.330 _refine_ls_restrained_S_all 1.330 _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 N3 N 0.3233(2) 0.11681(15) -0.02056(17) 0.0237(6) Uani 1 1 d . . . N1 N 0.3512(2) -0.19180(15) 0.03941(17) 0.0246(6) Uani 1 1 d . . . H1 H 0.3954 -0.2019 0.0815 0.030 Uiso 1 1 calc . . . C6 C 0.3558(2) 0.04638(16) -0.01946(16) 0.0157(5) Uani 1 1 d . . . N2 N 0.2308(2) 0.02287(16) -0.13529(16) 0.0232(5) Uani 1 1 d . . . H2 H 0.2379 0.0728 -0.1405 0.028 Uiso 1 1 calc . . . C1 C 0.4556(2) 0.01041(15) 0.02858(16) 0.0136(5) Uani 1 1 d . . . H1A H 0.4864 0.0478 0.0693 0.016 Uiso 1 1 calc . . . C2 C 0.4193(2) -0.06338(15) 0.06854(17) 0.0162(5) Uani 1 1 d . . . C3 C 0.3497(2) -0.11845(16) 0.01432(18) 0.0185(6) Uani 1 1 d . . . N4 N 0.4384(2) -0.08481(15) 0.13994(15) 0.0210(5) Uani 1 1 d . . . C4 C 0.2895(2) -0.09009(17) -0.05515(17) 0.0198(6) Uani 1 1 d . . . H4 H 0.2498 -0.1249 -0.0898 0.024 Uiso 1 1 calc . . . C5 C 0.2884(2) -0.01000(17) -0.07310(17) 0.0179(5) Uani 1 1 d . . . C18 C 0.4543(3) -0.0462(2) 0.28098(18) 0.0266(7) Uani 1 1 d . . . C7 C 0.2872(3) -0.25786(19) 0.0046(2) 0.0324(8) Uani 1 1 d . . . H7A H 0.3344 -0.3034 0.0038 0.039 Uiso 1 1 calc . . . H7B H 0.2597 -0.2453 -0.0501 0.039 Uiso 1 1 calc . . . C17 C 0.5039(3) -0.0403(2) 0.20185(19) 0.0280(7) Uani 1 1 d . . . H17A H 0.5068 0.0144 0.1859 0.034 Uiso 1 1 calc . . . H17B H 0.5781 -0.0605 0.2088 0.034 Uiso 1 1 calc . . . C22 C 0.3775(3) 0.17932(19) 0.0282(3) 0.0339(8) Uani 1 1 d . . . H22A H 0.4156 0.2135 -0.0055 0.041 Uiso 1 1 calc . . . H22B H 0.4316 0.1563 0.0679 0.041 Uiso 1 1 calc . . . C12 C 0.1563(3) -0.0171(2) -0.1961(2) 0.0292(7) Uani 1 1 d . . . H12A H 0.1724 -0.0729 -0.1942 0.035 Uiso 1 1 calc . . . H12B H 0.1696 0.0020 -0.2483 0.035 Uiso 1 1 calc . . . C8 C 0.1901(4) -0.2784(2) 0.0508(3) 0.0396(9) Uani 1 1 d . . . C23 C 0.2978(3) 0.2279(3) 0.0699(3) 0.0384(9) Uani 1 1 d . . . C19 C 0.4484(4) -0.1321(3) 0.3054(2) 0.0434(10) Uani 1 1 d . . . H19A H 0.4168 -0.1358 0.3547 0.065 Uiso 1 1 calc . . . H19B H 0.5208 -0.1541 0.3122 0.065 Uiso 1 1 calc . . . H19C H 0.4039 -0.1607 0.2646 0.065 Uiso 1 1 calc . . . C13 C 0.0345(3) -0.0052(2) -0.1862(3) 0.0362(9) Uani 1 1 d . . . C24 C 0.2267(6) 0.2722(4) 0.0012(4) 0.088(2) Uani 1 1 d . . . H24A H 0.1750 0.3054 0.0235 0.131 Uiso 1 1 calc . . . H24B H 0.1883 0.2347 -0.0342 0.131 Uiso 1 1 calc . . . H24C H 0.2733 0.3037 -0.0279 0.131 Uiso 1 1 calc . . . C20 C 0.3396(5) -0.0109(4) 0.2728(3) 0.0620(15) Uani 1 1 d . . . H20A H 0.3102 -0.0146 0.3229 0.093 Uiso 1 1 calc . . . H20B H 0.2934 -0.0391 0.2328 0.093 Uiso 1 1 calc . . . H20C H 0.3431 0.0433 0.2575 0.093 Uiso 1 1 calc . . . C11 C 0.1387(6) -0.3536(3) 0.0148(4) 0.076(2) Uani 1 1 d . . . H11A H 0.1147 -0.3454 -0.0407 0.114 Uiso 1 1 calc . . . H11B H 0.0772 -0.3678 0.0420 0.114 Uiso 1 1 calc . . . H11C H 0.1919 -0.3951 0.0204 0.114 Uiso 1 1 calc . . . C26 C 0.3588(5) 0.2905(3) 0.1207(4) 0.0661(17) Uani 1 1 d . . . H26A H 0.3079 0.3205 0.1474 0.099 Uiso 1 1 calc . . . H26B H 0.3959 0.3246 0.0873 0.099 Uiso 1 1 calc . . . H26C H 0.4114 0.2661 0.1595 0.099 Uiso 1 1 calc . . . C16 C 0.0047(4) 0.0807(3) -0.1956(5) 0.082(2) Uani 1 1 d . . . H16A H 0.0208 0.0989 -0.2468 0.123 Uiso 1 1 calc . . . H16B H 0.0463 0.1106 -0.1544 0.123 Uiso 1 1 calc . . . H16C H -0.0720 0.0873 -0.1915 0.123 Uiso 1 1 calc . . . C15 C -0.0325(4) -0.0555(4) -0.2480(4) 0.083(2) Uani 1 1 d . . . H15A H -0.0192 -0.0392 -0.3005 0.124 Uiso 1 1 calc . . . H15B H -0.1088 -0.0496 -0.2424 0.124 Uiso 1 1 calc . . . H15C H -0.0119 -0.1096 -0.2402 0.124 Uiso 1 1 calc . . . C21 C 0.5302(5) -0.0023(3) 0.3432(2) 0.0518(13) Uani 1 1 d . . . H21A H 0.5025 -0.0057 0.3939 0.078 Uiso 1 1 calc . . . H21B H 0.5343 0.0519 0.3278 0.078 Uiso 1 1 calc . . . H21C H 0.6019 -0.0253 0.3471 0.078 Uiso 1 1 calc . . . C10 C 0.2251(5) -0.2910(4) 0.1384(3) 0.0740(19) Uani 1 1 d . . . H10A H 0.2634 -0.2453 0.1602 0.111 Uiso 1 1 calc . . . H10B H 0.2725 -0.3359 0.1454 0.111 Uiso 1 1 calc . . . H10C H 0.1617 -0.2998 0.1655 0.111 Uiso 1 1 calc . . . C9 C 0.1052(5) -0.2139(4) 0.0360(5) 0.089(2) Uani 1 1 d . . . H9A H 0.0873 -0.2066 -0.0204 0.134 Uiso 1 1 calc . . . H9B H 0.1341 -0.1659 0.0597 0.134 Uiso 1 1 calc . . . H9C H 0.0406 -0.2285 0.0593 0.134 Uiso 1 1 calc . . . C25 C 0.2386(10) 0.1783(6) 0.1222(5) 0.146(5) Uani 1 1 d . . . H25A H 0.1959 0.2110 0.1531 0.219 Uiso 1 1 calc . . . H25B H 0.2902 0.1486 0.1573 0.219 Uiso 1 1 calc . . . H25C H 0.1911 0.1430 0.0902 0.219 Uiso 1 1 calc . . . C14 C 0.0109(4) -0.0343(5) -0.1038(4) 0.081(2) Uani 1 1 d . . . H14A H 0.0516 -0.0033 -0.0631 0.122 Uiso 1 1 calc . . . H14B H 0.0322 -0.0884 -0.0974 0.122 Uiso 1 1 calc . . . H14C H -0.0659 -0.0294 -0.0994 0.122 Uiso 1 1 calc . . . C27 C 0.3514(4) -0.2028(3) -0.2603(3) 0.0437(10) Uani 1 1 d . . . F1 F 0.2921(3) -0.1515(2) -0.3103(2) 0.0730(9) Uani 1 1 d . . . F2 F 0.4282(3) -0.23213(19) -0.3016(2) 0.0709(10) Uani 1 1 d . . . F3 F 0.3991(3) -0.1617(2) -0.2014(2) 0.0795(11) Uani 1 1 d . . . S1 S 0.26371(9) -0.27916(7) -0.22779(6) 0.0416(3) Uani 1 1 d . . . O1 O 0.3355(4) -0.3260(3) -0.1744(2) 0.0552(10) Uani 0.83 1 d P . . O2 O 0.1799(3) -0.2317(2) -0.1929(2) 0.0390(8) Uani 0.83 1 d P . . O3 O 0.2204(3) -0.3186(2) -0.2980(2) 0.0463(9) Uani 0.83 1 d P . . O4 O 0.1790(5) -0.2573(3) -0.2693(3) 0.0344(12) Uani 0.50 1 d P . . O5 O 0.5182(4) -0.2691(3) 0.1383(3) 0.0736(12) Uani 1 1 d D . . H1O H 0.466(3) -0.277(3) 0.168(2) 0.050 Uiso 1 1 d D . . H2O H 0.582(2) -0.250(3) 0.157(2) 0.050 Uiso 1 1 d 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 N3 0.0197(13) 0.0159(12) 0.0357(14) 0.0001(10) 0.0047(11) 0.0010(9) N1 0.0282(14) 0.0156(12) 0.0302(14) 0.0030(10) 0.0045(11) -0.0039(10) C6 0.0122(12) 0.0165(12) 0.0191(12) 0.0003(10) 0.0052(9) -0.0004(9) N2 0.0166(12) 0.0266(13) 0.0259(13) 0.0016(10) -0.0002(10) 0.0002(9) C1 0.0149(12) 0.0098(11) 0.0166(12) 0.0009(9) 0.0039(9) -0.0013(9) C2 0.0165(13) 0.0123(11) 0.0209(13) 0.0014(10) 0.0068(10) -0.0031(9) C3 0.0186(13) 0.0148(12) 0.0232(13) -0.0018(10) 0.0078(11) -0.0041(10) N4 0.0221(13) 0.0207(12) 0.0201(12) 0.0023(9) 0.0026(9) -0.0043(9) C4 0.0213(14) 0.0183(13) 0.0200(13) -0.0053(10) 0.0025(11) -0.0053(10) C5 0.0129(12) 0.0205(13) 0.0206(13) -0.0013(10) 0.0041(10) -0.0024(10) C18 0.0294(17) 0.0306(17) 0.0196(14) 0.0046(12) 0.0023(12) -0.0017(13) C7 0.044(2) 0.0159(14) 0.0381(19) -0.0031(13) 0.0069(16) -0.0114(13) C17 0.0310(17) 0.0322(17) 0.0201(14) 0.0068(12) 0.0006(12) -0.0125(13) C22 0.0267(17) 0.0155(14) 0.059(2) -0.0095(15) 0.0037(16) -0.0002(12) C12 0.0235(16) 0.0377(19) 0.0249(15) -0.0072(13) -0.0037(12) 0.0039(13) C8 0.044(2) 0.0317(19) 0.044(2) 0.0034(16) 0.0092(18) -0.0192(16) C23 0.0272(18) 0.044(2) 0.042(2) -0.0184(17) -0.0013(15) 0.0060(15) C19 0.062(3) 0.040(2) 0.0287(18) 0.0146(16) 0.0092(18) -0.0105(19) C13 0.0181(15) 0.039(2) 0.050(2) -0.0132(17) -0.0048(14) -0.0010(14) C24 0.087(5) 0.088(5) 0.080(4) -0.038(4) -0.025(4) 0.059(4) C20 0.059(3) 0.080(4) 0.048(3) -0.011(3) 0.009(2) 0.029(3) C11 0.100(5) 0.057(3) 0.069(3) 0.004(3) -0.003(3) -0.056(3) C26 0.067(3) 0.043(3) 0.082(4) -0.037(3) -0.021(3) 0.017(2) C16 0.026(2) 0.049(3) 0.168(7) -0.007(4) 0.003(3) 0.014(2) C15 0.035(3) 0.108(5) 0.098(5) -0.061(4) -0.025(3) 0.010(3) C21 0.071(3) 0.063(3) 0.0197(16) 0.0025(17) -0.0038(18) -0.027(2) C10 0.081(4) 0.091(4) 0.050(3) 0.020(3) 0.006(3) -0.051(4) C9 0.044(3) 0.070(4) 0.163(7) 0.035(4) 0.048(4) -0.001(3) C25 0.240(12) 0.115(7) 0.107(6) -0.059(5) 0.125(8) -0.092(8) C14 0.034(3) 0.136(6) 0.075(4) 0.013(4) 0.014(3) -0.023(3) C27 0.045(2) 0.037(2) 0.051(2) -0.0077(19) 0.0125(19) -0.0037(17) F1 0.076(2) 0.062(2) 0.084(2) 0.0130(18) 0.0239(18) -0.0087(17) F2 0.075(2) 0.063(2) 0.084(2) -0.0150(17) 0.0484(18) -0.0087(16) F3 0.070(2) 0.081(2) 0.091(2) -0.040(2) 0.0184(19) -0.0342(18) S1 0.0446(6) 0.0401(6) 0.0408(6) -0.0103(4) 0.0088(4) -0.0082(4) O1 0.063(3) 0.060(3) 0.044(2) 0.0158(18) 0.0097(19) 0.013(2) O2 0.0459(19) 0.0368(17) 0.0376(17) -0.0193(14) 0.0193(15) -0.0197(14) O3 0.0408(19) 0.0364(18) 0.062(2) -0.0313(17) 0.0066(17) -0.0131(14) O4 0.059(4) 0.024(2) 0.022(2) -0.0049(18) 0.012(2) -0.004(2) O5 0.070(3) 0.057(2) 0.089(3) 0.015(2) -0.012(2) 0.008(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 N3 C6 1.263(4) . ? N3 C22 1.458(4) . ? N1 C3 1.318(4) . ? N1 C7 1.456(4) . ? C6 C5 1.501(4) . ? C6 C1 1.520(4) . ? N2 C5 1.320(4) . ? N2 C12 1.463(4) . ? C1 C2 1.517(4) . ? C1 C1 1.579(5) 3_655 ? C2 N4 1.255(4) . ? C2 C3 1.506(4) . ? C3 C4 1.398(4) . ? N4 C17 1.456(4) . ? C4 C5 1.396(4) . ? C18 C21 1.519(5) . ? C18 C19 1.523(5) . ? C18 C20 1.525(6) . ? C18 C17 1.535(5) . ? C7 C8 1.541(6) . ? C22 C23 1.517(5) . ? C12 C13 1.541(5) . ? C8 C10 1.507(7) . ? C8 C9 1.515(8) . ? C8 C11 1.522(6) . ? C23 C25 1.473(9) . ? C23 C26 1.511(6) . ? C23 C24 1.563(8) . ? C13 C16 1.511(7) . ? C13 C15 1.518(6) . ? C13 C14 1.536(8) . ? C27 F3 1.299(5) . ? C27 F2 1.335(5) . ? C27 F1 1.366(6) . ? C27 S1 1.814(5) . ? S1 O4 1.244(6) . ? S1 O3 1.412(3) . ? S1 O1 1.429(4) . ? S1 O2 1.484(4) . ? O2 O4 1.360(6) . ? O3 O4 1.281(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 C6 N3 C22 124.2(3) . . ? C3 N1 C7 128.0(3) . . ? N3 C6 C5 116.5(3) . . ? N3 C6 C1 128.7(3) . . ? C5 C6 C1 114.8(2) . . ? C5 N2 C12 126.6(3) . . ? C2 C1 C6 108.0(2) . . ? C2 C1 C1 110.3(3) . 3_655 ? C6 C1 C1 109.8(3) . 3_655 ? N4 C2 C3 115.7(2) . . ? N4 C2 C1 129.4(3) . . ? C3 C2 C1 114.9(2) . . ? N1 C3 C4 125.7(3) . . ? N1 C3 C2 114.1(3) . . ? C4 C3 C2 120.2(2) . . ? C2 N4 C17 124.4(3) . . ? C5 C4 C3 120.7(3) . . ? N2 C5 C4 125.3(3) . . ? N2 C5 C6 114.6(3) . . ? C4 C5 C6 120.1(3) . . ? C21 C18 C19 109.3(3) . . ? C21 C18 C20 110.9(4) . . ? C19 C18 C20 109.3(4) . . ? C21 C18 C17 107.1(3) . . ? C19 C18 C17 109.6(3) . . ? C20 C18 C17 110.6(3) . . ? N1 C7 C8 112.7(3) . . ? N4 C17 C18 110.3(3) . . ? N3 C22 C23 112.5(3) . . ? N2 C12 C13 113.6(3) . . ? C10 C8 C9 112.2(6) . . ? C10 C8 C11 109.3(4) . . ? C9 C8 C11 107.3(5) . . ? C10 C8 C7 112.2(4) . . ? C9 C8 C7 108.2(3) . . ? C11 C8 C7 107.4(4) . . ? C25 C23 C26 108.2(5) . . ? C25 C23 C22 110.9(5) . . ? C26 C23 C22 110.0(4) . . ? C25 C23 C24 116.6(7) . . ? C26 C23 C24 106.2(4) . . ? C22 C23 C24 104.7(4) . . ? C16 C13 C15 111.6(5) . . ? C16 C13 C14 109.7(5) . . ? C15 C13 C14 107.2(5) . . ? C16 C13 C12 110.1(4) . . ? C15 C13 C12 108.0(3) . . ? C14 C13 C12 110.2(4) . . ? F3 C27 F2 108.5(4) . . ? F3 C27 F1 106.9(4) . . ? F2 C27 F1 106.0(4) . . ? F3 C27 S1 112.7(3) . . ? F2 C27 S1 111.8(3) . . ? F1 C27 S1 110.5(3) . . ? O4 S1 O3 57.2(3) . . ? O4 S1 O1 159.8(3) . . ? O3 S1 O1 114.1(3) . . ? O4 S1 O2 59.0(3) . . ? O3 S1 O2 112.4(2) . . ? O1 S1 O2 117.5(2) . . ? O4 S1 C27 96.0(3) . . ? O3 S1 C27 105.5(2) . . ? O1 S1 C27 104.1(2) . . ? O2 S1 C27 101.2(2) . . ? O4 O2 S1 51.6(3) . . ? O4 O3 S1 54.8(3) . . ? S1 O4 O3 68.0(3) . . ? S1 O4 O2 69.3(3) . . ? O3 O4 O2 131.3(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.131 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.159