# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Carl Schiesser' _publ_contact_author_email carlhs@unimelb.edu.au _publ_section_title ; Novel Paramagnetic AT1 Receptor Antagonists ; loop_ _publ_author_name N.Tan M.Taylor S.Bottle C.Wright J.Ziogas J.White C.Schiesser ; N.Jani ; # Attachment '- 4-Me.cif' data_jmwnt13 _database_code_depnum_ccdc_archive 'CCDC 833015' #TrackingRef '- 4-Me.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C31 H32 N7 O).(C2 H8 O2)' _chemical_formula_sum 'C35 H40 N7 O3 S' _chemical_formula_weight 638.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P b c a' _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.5680(7) _cell_length_b 11.9747(5) _cell_length_c 35.0893(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6541.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2120 _cell_measurement_theta_min 3.1029 _cell_measurement_theta_max 73.2163 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3670 _exptl_crystal_size_mid 0.3000 _exptl_crystal_size_min 0.0200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2712 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_T_min 0.90025 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _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 14967 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.1395 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 67.50 _reflns_number_total 5883 _reflns_number_gt 2600 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution ? _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. Disordered ethyl acetate solvent was treated using the Squeeze procedure. ; _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^)+(0.0337P)^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 5883 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 0.712 _refine_ls_restrained_S_all 0.712 _refine_ls_shift/su_max 0.002 _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 C1 C -0.01395(18) 0.3504(3) 0.15942(8) 0.0356(8) Uani 1 1 d . . . C2 C 0.00322(19) 0.2405(3) 0.15671(8) 0.0340(7) Uani 1 1 d . . . C3 C 0.07563(18) 0.2151(3) 0.13372(8) 0.0377(8) Uani 1 1 d . . . H3 H 0.0960 0.1432 0.1293 0.045 Uiso 1 1 calc R . . C4 C 0.11148(19) 0.3098(3) 0.11895(8) 0.0371(8) Uani 1 1 d . . . C5 C 0.18578(19) 0.3186(3) 0.09172(8) 0.0441(9) Uani 1 1 d . . . H5A H 0.2280 0.3700 0.1020 0.053 Uiso 1 1 calc R . . H5B H 0.2129 0.2461 0.0892 0.053 Uiso 1 1 calc R . . C6 C 0.1205(2) 0.2880(3) 0.02829(9) 0.0370(8) Uani 1 1 d . . . C7 C 0.10144(17) 0.4329(3) -0.01425(8) 0.0335(7) Uani 1 1 d . . . C8 C 0.13979(18) 0.5070(3) 0.00877(8) 0.0329(7) Uani 1 1 d . . . C9 C 0.16622(19) 0.4741(3) 0.04654(9) 0.0365(8) Uani 1 1 d . . . C10 C 0.15361(18) 0.6271(2) -0.00204(8) 0.0350(8) Uani 1 1 d . . . H10A H 0.1717 0.6682 0.0204 0.042 Uiso 1 1 calc R . . H10B H 0.0993 0.6584 -0.0104 0.042 Uiso 1 1 calc R . . C11 C 0.21969(18) 0.6438(2) -0.03322(8) 0.0315(7) Uani 1 1 d . . . C12 C 0.28410(18) 0.5669(2) -0.04069(8) 0.0331(7) Uani 1 1 d . . . H12 H 0.2865 0.5014 -0.0265 0.040 Uiso 1 1 calc R . . C13 C 0.34509(18) 0.5851(2) -0.06879(8) 0.0318(7) Uani 1 1 d . . . H13 H 0.3872 0.5316 -0.0732 0.038 Uiso 1 1 calc R . . C14 C 0.34421(18) 0.6826(3) -0.09057(8) 0.0309(7) Uani 1 1 d . . . C15 C 0.27921(19) 0.7588(3) -0.08363(8) 0.0361(8) Uani 1 1 d . . . H15 H 0.2765 0.8237 -0.0981 0.043 Uiso 1 1 calc R . . C16 C 0.21795(19) 0.7407(2) -0.05547(8) 0.0342(7) Uani 1 1 d . . . H16 H 0.1753 0.7937 -0.0514 0.041 Uiso 1 1 calc R . . C17 C 0.4077(2) 0.7019(2) -0.12165(8) 0.0356(8) Uani 1 1 d . . . C18 C 0.4968(2) 0.6877(3) -0.11725(9) 0.0395(8) Uani 1 1 d . . . C19 C 0.5509(2) 0.7038(3) -0.14845(10) 0.0561(10) Uani 1 1 d . . . H25 H 0.6098 0.6945 -0.1455 0.067 Uiso 1 1 calc R . . C20 C 0.5186(3) 0.7332(3) -0.18361(10) 0.0610(11) Uani 1 1 d . . . H26 H 0.5557 0.7432 -0.2041 0.073 Uiso 1 1 calc R . . C21 C 0.4314(2) 0.7479(3) -0.18836(10) 0.0568(10) Uani 1 1 d . . . H27 H 0.4091 0.7674 -0.2120 0.068 Uiso 1 1 calc R . . C22 C 0.3772(2) 0.7333(3) -0.15717(9) 0.0445(9) Uani 1 1 d . . . H28 H 0.3186 0.7450 -0.1603 0.053 Uiso 1 1 calc R . . C23 C 0.53894(19) 0.6564(3) -0.08119(9) 0.0354(8) Uani 1 1 d . . . C24 C 0.1102(2) 0.1673(2) 0.03834(9) 0.0459(9) Uani 1 1 d . . . H24A H 0.1646 0.1374 0.0463 0.069 Uiso 1 1 calc R . . H24B H 0.0900 0.1269 0.0165 0.069 Uiso 1 1 calc R . . H24C H 0.0694 0.1600 0.0587 0.069 Uiso 1 1 calc R . . C25 C 0.06694(18) 0.4631(2) -0.05334(8) 0.0364(8) Uani 1 1 d . . . H25A H 0.1101 0.4483 -0.0722 0.055 Uiso 1 1 calc R . . H25B H 0.0521 0.5409 -0.0539 0.055 Uiso 1 1 calc R . . H25C H 0.0168 0.4191 -0.0587 0.055 Uiso 1 1 calc R . . C26 C -0.0623(2) 0.1713(3) 0.17797(8) 0.0388(8) Uani 1 1 d . . . C27 C -0.1135(2) 0.0942(3) 0.15174(9) 0.0536(10) Uani 1 1 d . . . H27A H -0.0771 0.0347 0.1430 0.080 Uiso 1 1 calc R . . H27B H -0.1341 0.1359 0.1302 0.080 Uiso 1 1 calc R . . H27C H -0.1613 0.0636 0.1655 0.080 Uiso 1 1 calc R . . C28 C -0.0259(2) 0.1076(3) 0.21169(9) 0.0543(10) Uani 1 1 d . . . H28A H 0.0125 0.0507 0.2027 0.081 Uiso 1 1 calc R . . H28B H -0.0720 0.0736 0.2257 0.081 Uiso 1 1 calc R . . H28C H 0.0048 0.1581 0.2280 0.081 Uiso 1 1 calc R . . C29 C -0.0910(2) 0.3802(3) 0.18264(9) 0.0405(8) Uani 1 1 d . . . C30 C -0.16190(19) 0.4388(3) 0.16010(10) 0.0540(10) Uani 1 1 d . . . H30A H -0.1720 0.3992 0.1367 0.081 Uiso 1 1 calc R . . H30B H -0.1446 0.5140 0.1545 0.081 Uiso 1 1 calc R . . H30C H -0.2137 0.4400 0.1749 0.081 Uiso 1 1 calc R . . C31 C -0.0697(2) 0.4421(3) 0.21895(9) 0.0610(11) Uani 1 1 d . . . H31A H -0.0521 0.5169 0.2129 0.091 Uiso 1 1 calc R . . H31B H -0.0239 0.4044 0.2320 0.091 Uiso 1 1 calc R . . H31C H -0.1195 0.4445 0.2351 0.091 Uiso 1 1 calc R . . N1 N 0.15805(15) 0.3582(2) 0.05373(7) 0.0368(7) Uani 1 1 d . . . N2 N 0.09173(15) 0.3215(2) -0.00469(7) 0.0331(6) Uani 1 1 d . . . N3 N 0.51630(16) 0.6827(2) -0.04555(8) 0.0376(7) Uani 1 1 d . . . N4 N 0.57453(16) 0.6389(2) -0.02116(8) 0.0441(7) Uani 1 1 d . . . N5 N 0.63098(17) 0.5871(2) -0.04216(9) 0.0471(7) Uani 1 1 d . . . N6 N 0.61050(16) 0.5949(2) -0.07968(8) 0.0464(7) Uani 1 1 d . . . N7 N -0.11942(17) 0.2634(2) 0.19163(8) 0.0478(8) Uani 1 1 d . . . O1 O -0.18598(16) 0.2445(2) 0.21164(8) 0.0702(8) Uani 1 1 d . . . O2 O 0.19113(13) 0.53589(18) 0.07185(6) 0.0453(6) Uani 1 1 d . . . S1 S 0.05774(5) 0.43049(7) 0.13395(2) 0.0403(2) Uani 1 1 d . . . H4 H 0.473(2) 0.741(3) -0.0317(10) 0.096(14) Uiso 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 0.0311(16) 0.041(2) 0.0347(17) 0.0059(16) -0.0012(14) -0.0050(15) C2 0.0307(17) 0.040(2) 0.0312(16) 0.0026(15) -0.0050(13) 0.0011(16) C3 0.0335(18) 0.047(2) 0.0323(16) 0.0048(16) -0.0024(14) 0.0070(15) C4 0.0324(17) 0.042(2) 0.0371(17) 0.0073(16) -0.0027(14) 0.0064(16) C5 0.0342(18) 0.057(2) 0.0414(19) 0.0111(18) 0.0030(15) 0.0037(17) C6 0.0360(18) 0.037(2) 0.0384(19) 0.0016(16) 0.0173(15) 0.0046(15) C7 0.0301(16) 0.033(2) 0.0375(17) 0.0031(16) 0.0097(13) 0.0063(15) C8 0.0297(16) 0.036(2) 0.0335(17) 0.0008(15) 0.0105(14) 0.0030(15) C9 0.0291(17) 0.039(2) 0.0417(19) -0.0020(17) 0.0084(14) 0.0039(15) C10 0.0363(17) 0.0311(19) 0.0376(18) -0.0013(15) 0.0018(14) 0.0057(15) C11 0.0329(16) 0.0277(19) 0.0338(17) 0.0004(14) -0.0029(13) -0.0013(14) C12 0.0390(17) 0.0265(18) 0.0337(16) 0.0043(15) -0.0023(14) -0.0013(15) C13 0.0300(15) 0.0303(19) 0.0349(16) -0.0017(15) -0.0010(13) -0.0011(15) C14 0.0290(16) 0.0310(19) 0.0326(16) 0.0003(15) -0.0063(13) -0.0045(14) C15 0.0360(17) 0.033(2) 0.0396(17) 0.0080(15) -0.0069(15) -0.0043(16) C16 0.0305(16) 0.0289(19) 0.0433(18) 0.0010(16) -0.0048(14) 0.0020(15) C17 0.0432(19) 0.030(2) 0.0336(17) 0.0005(14) -0.0009(14) -0.0039(15) C18 0.0396(19) 0.033(2) 0.0462(19) 0.0021(17) 0.0048(15) -0.0025(17) C19 0.043(2) 0.064(3) 0.062(2) 0.004(2) 0.0100(18) -0.003(2) C20 0.067(3) 0.072(3) 0.045(2) 0.009(2) 0.024(2) -0.006(2) C21 0.071(3) 0.059(3) 0.040(2) 0.0031(19) 0.004(2) -0.004(2) C22 0.049(2) 0.040(2) 0.045(2) 0.0017(17) 0.0018(17) -0.0074(17) C23 0.0336(18) 0.028(2) 0.0448(19) 0.0033(16) 0.0018(14) -0.0079(14) C24 0.058(2) 0.038(2) 0.0421(19) 0.0069(17) 0.0098(17) 0.0063(17) C25 0.0355(18) 0.038(2) 0.0357(17) 0.0028(15) 0.0039(14) -0.0010(15) C26 0.0390(18) 0.042(2) 0.0348(17) 0.0025(16) 0.0005(14) -0.0041(16) C27 0.051(2) 0.049(2) 0.060(2) -0.0026(19) -0.0042(19) -0.0106(19) C28 0.055(2) 0.063(3) 0.044(2) 0.0179(19) 0.0033(17) -0.0037(19) C29 0.0420(19) 0.041(2) 0.0382(18) -0.0029(16) 0.0038(15) -0.0047(16) C30 0.044(2) 0.048(2) 0.070(3) -0.002(2) 0.0005(18) 0.0102(18) C31 0.073(3) 0.062(3) 0.048(2) -0.014(2) 0.008(2) -0.001(2) N1 0.0331(15) 0.0402(18) 0.0371(15) 0.0040(13) 0.0071(12) -0.0002(13) N2 0.0339(14) 0.0322(16) 0.0330(14) 0.0041(13) 0.0096(11) -0.0010(12) N3 0.0330(14) 0.0323(17) 0.0476(17) 0.0025(14) -0.0088(13) -0.0014(13) N4 0.0374(16) 0.0301(17) 0.0646(19) 0.0034(14) -0.0117(14) 0.0000(13) N5 0.0406(16) 0.0343(18) 0.066(2) 0.0057(16) -0.0071(15) -0.0002(14) N6 0.0323(15) 0.0416(19) 0.066(2) 0.0055(16) 0.0088(14) 0.0022(14) N7 0.0426(17) 0.0443(19) 0.0566(19) -0.0014(15) 0.0146(15) -0.0030(14) O1 0.0572(16) 0.0672(19) 0.086(2) 0.0048(16) 0.0322(15) -0.0013(15) O2 0.0450(14) 0.0499(16) 0.0411(13) -0.0050(12) 0.0002(11) 0.0013(11) S1 0.0410(4) 0.0426(5) 0.0373(4) 0.0046(4) -0.0011(4) -0.0029(4) _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 C2 1.345(4) . ? C1 C29 1.493(4) . ? C1 S1 1.722(3) . ? C2 C3 1.419(4) . ? C2 C26 1.511(4) . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 C5 1.504(4) . ? C4 S1 1.751(3) . ? C5 N1 1.479(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N2 1.304(4) . ? C6 N1 1.358(4) . ? C6 C24 1.497(4) . ? C7 C8 1.340(4) . ? C7 N2 1.383(4) . ? C7 C25 1.517(4) . ? C8 C9 1.442(4) . ? C8 C10 1.504(4) . ? C9 O2 1.219(3) . ? C9 N1 1.417(4) . ? C10 C11 1.515(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.386(4) . ? C11 C16 1.399(4) . ? C12 C13 1.386(4) . ? C12 H12 0.9300 . ? C13 C14 1.395(4) . ? C13 H13 0.9300 . ? C14 C15 1.385(4) . ? C14 C17 1.490(4) . ? C15 C16 1.390(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.385(4) . ? C17 C18 1.406(4) . ? C18 C19 1.394(4) . ? C18 C23 1.474(4) . ? C19 C20 1.378(5) . ? C19 H25 0.9300 . ? C20 C21 1.379(5) . ? C20 H26 0.9300 . ? C21 C22 1.393(4) . ? C21 H27 0.9300 . ? C22 H28 0.9300 . ? C23 N6 1.336(4) . ? C23 N3 1.337(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N7 1.495(4) . ? C26 C28 1.518(4) . ? C26 C27 1.528(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 N7 1.501(4) . ? C29 C31 1.511(4) . ? C29 C30 1.529(4) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? N3 N4 1.352(3) . ? N3 H4 1.09(4) . ? N4 N5 1.304(3) . ? N5 N6 1.358(4) . ? N7 O1 1.272(3) . ? 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 C2 C1 C29 115.6(3) . . ? C2 C1 S1 112.3(2) . . ? C29 C1 S1 132.1(3) . . ? C1 C2 C3 114.1(3) . . ? C1 C2 C26 111.5(3) . . ? C3 C2 C26 134.3(3) . . ? C4 C3 C2 111.2(3) . . ? C4 C3 H3 124.4 . . ? C2 C3 H3 124.4 . . ? C3 C4 C5 127.9(3) . . ? C3 C4 S1 112.1(2) . . ? C5 C4 S1 120.0(2) . . ? N1 C5 C4 111.8(2) . . ? N1 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N2 C6 N1 122.7(3) . . ? N2 C6 C24 118.0(3) . . ? N1 C6 C24 119.2(3) . . ? C8 C7 N2 122.7(3) . . ? C8 C7 C25 123.0(3) . . ? N2 C7 C25 114.2(3) . . ? C7 C8 C9 120.0(3) . . ? C7 C8 C10 123.0(3) . . ? C9 C8 C10 116.9(3) . . ? O2 C9 N1 119.6(3) . . ? O2 C9 C8 126.5(3) . . ? N1 C9 C8 113.9(3) . . ? C8 C10 C11 113.9(2) . . ? C8 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C8 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C16 117.4(3) . . ? C12 C11 C10 122.7(3) . . ? C16 C11 C10 120.0(3) . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 121.0(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 117.5(3) . . ? C15 C14 C17 120.8(3) . . ? C13 C14 C17 121.6(3) . . ? C14 C15 C16 121.6(3) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C22 C17 C18 118.0(3) . . ? C22 C17 C14 118.3(3) . . ? C18 C17 C14 123.7(3) . . ? C19 C18 C17 119.5(3) . . ? C19 C18 C23 116.2(3) . . ? C17 C18 C23 124.3(3) . . ? C20 C19 C18 121.3(3) . . ? C20 C19 H25 119.4 . . ? C18 C19 H25 119.4 . . ? C19 C20 C21 119.9(3) . . ? C19 C20 H26 120.0 . . ? C21 C20 H26 120.0 . . ? C20 C21 C22 119.0(3) . . ? C20 C21 H27 120.5 . . ? C22 C21 H27 120.5 . . ? C17 C22 C21 122.3(3) . . ? C17 C22 H28 118.9 . . ? C21 C22 H28 118.9 . . ? N6 C23 N3 108.2(3) . . ? N6 C23 C18 123.1(3) . . ? N3 C23 C18 128.7(3) . . ? C6 C24 H24A 109.5 . . ? C6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C7 C25 H25A 109.5 . . ? C7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N7 C26 C2 98.9(3) . . ? N7 C26 C28 110.1(3) . . ? C2 C26 C28 114.1(3) . . ? N7 C26 C27 109.2(3) . . ? C2 C26 C27 112.7(3) . . ? C28 C26 C27 111.1(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C1 C29 N7 97.4(2) . . ? C1 C29 C31 113.7(3) . . ? N7 C29 C31 110.2(3) . . ? C1 C29 C30 114.1(3) . . ? N7 C29 C30 108.9(3) . . ? C31 C29 C30 111.7(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C6 N1 C9 121.8(3) . . ? C6 N1 C5 121.3(3) . . ? C9 N1 C5 116.6(3) . . ? C6 N2 C7 118.3(3) . . ? C23 N3 N4 108.9(3) . . ? C23 N3 H4 137.1(19) . . ? N4 N3 H4 112.6(19) . . ? N5 N4 N3 106.2(3) . . ? N4 N5 N6 110.9(2) . . ? C23 N6 N5 105.8(3) . . ? O1 N7 C26 122.0(3) . . ? O1 N7 C29 121.5(3) . . ? C26 N7 C29 116.4(2) . . ? C1 S1 C4 90.32(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C29 C1 C2 C3 178.6(3) . . . . ? S1 C1 C2 C3 -0.1(3) . . . . ? C29 C1 C2 C26 0.9(4) . . . . ? S1 C1 C2 C26 -177.8(2) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C26 C2 C3 C4 176.3(3) . . . . ? C2 C3 C4 C5 -176.6(3) . . . . ? C2 C3 C4 S1 1.1(3) . . . . ? C3 C4 C5 N1 110.8(4) . . . . ? S1 C4 C5 N1 -66.7(4) . . . . ? N2 C7 C8 C9 -5.5(4) . . . . ? C25 C7 C8 C9 176.1(2) . . . . ? N2 C7 C8 C10 177.6(3) . . . . ? C25 C7 C8 C10 -0.9(4) . . . . ? C7 C8 C9 O2 -169.7(3) . . . . ? C10 C8 C9 O2 7.4(5) . . . . ? C7 C8 C9 N1 7.8(4) . . . . ? C10 C8 C9 N1 -175.0(2) . . . . ? C7 C8 C10 C11 -69.6(4) . . . . ? C9 C8 C10 C11 113.3(3) . . . . ? C8 C10 C11 C12 -23.9(4) . . . . ? C8 C10 C11 C16 157.1(3) . . . . ? C16 C11 C12 C13 0.6(4) . . . . ? C10 C11 C12 C13 -178.5(3) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C12 C13 C14 C15 -1.4(4) . . . . ? C12 C13 C14 C17 -178.1(3) . . . . ? C13 C14 C15 C16 1.4(4) . . . . ? C17 C14 C15 C16 178.1(3) . . . . ? C14 C15 C16 C11 -0.4(5) . . . . ? C12 C11 C16 C15 -0.6(4) . . . . ? C10 C11 C16 C15 178.5(3) . . . . ? C15 C14 C17 C22 -47.3(4) . . . . ? C13 C14 C17 C22 129.3(3) . . . . ? C15 C14 C17 C18 134.1(3) . . . . ? C13 C14 C17 C18 -49.3(4) . . . . ? C22 C17 C18 C19 -1.0(5) . . . . ? C14 C17 C18 C19 177.6(3) . . . . ? C22 C17 C18 C23 179.0(3) . . . . ? C14 C17 C18 C23 -2.4(5) . . . . ? C17 C18 C19 C20 -0.1(6) . . . . ? C23 C18 C19 C20 180.0(3) . . . . ? C18 C19 C20 C21 0.4(6) . . . . ? C19 C20 C21 C22 0.4(6) . . . . ? C18 C17 C22 C21 1.8(5) . . . . ? C14 C17 C22 C21 -176.9(3) . . . . ? C20 C21 C22 C17 -1.5(5) . . . . ? C19 C18 C23 N6 -32.3(5) . . . . ? C17 C18 C23 N6 147.8(3) . . . . ? C19 C18 C23 N3 146.7(3) . . . . ? C17 C18 C23 N3 -33.3(5) . . . . ? C1 C2 C26 N7 1.7(3) . . . . ? C3 C2 C26 N7 -175.4(3) . . . . ? C1 C2 C26 C28 -115.1(3) . . . . ? C3 C2 C26 C28 67.7(4) . . . . ? C1 C2 C26 C27 116.9(3) . . . . ? C3 C2 C26 C27 -60.2(5) . . . . ? C2 C1 C29 N7 -2.9(3) . . . . ? S1 C1 C29 N7 175.4(2) . . . . ? C2 C1 C29 C31 113.0(3) . . . . ? S1 C1 C29 C31 -68.7(4) . . . . ? C2 C1 C29 C30 -117.4(3) . . . . ? S1 C1 C29 C30 60.9(4) . . . . ? N2 C6 N1 C9 2.0(4) . . . . ? C24 C6 N1 C9 -177.2(3) . . . . ? N2 C6 N1 C5 176.7(3) . . . . ? C24 C6 N1 C5 -2.5(4) . . . . ? O2 C9 N1 C6 171.5(3) . . . . ? C8 C9 N1 C6 -6.2(4) . . . . ? O2 C9 N1 C5 -3.5(4) . . . . ? C8 C9 N1 C5 178.8(2) . . . . ? C4 C5 N1 C6 -79.1(4) . . . . ? C4 C5 N1 C9 95.9(3) . . . . ? N1 C6 N2 C7 1.1(4) . . . . ? C24 C6 N2 C7 -179.7(2) . . . . ? C8 C7 N2 C6 0.7(4) . . . . ? C25 C7 N2 C6 179.3(2) . . . . ? N6 C23 N3 N4 0.8(4) . . . . ? C18 C23 N3 N4 -178.3(3) . . . . ? C23 N3 N4 N5 -0.1(3) . . . . ? N3 N4 N5 N6 -0.7(3) . . . . ? N3 C23 N6 N5 -1.2(3) . . . . ? C18 C23 N6 N5 177.9(3) . . . . ? N4 N5 N6 C23 1.2(4) . . . . ? C2 C26 N7 O1 -179.9(3) . . . . ? C28 C26 N7 O1 -60.1(4) . . . . ? C27 C26 N7 O1 62.2(4) . . . . ? C2 C26 N7 C29 -3.8(3) . . . . ? C28 C26 N7 C29 116.1(3) . . . . ? C27 C26 N7 C29 -121.7(3) . . . . ? C1 C29 N7 O1 -179.7(3) . . . . ? C31 C29 N7 O1 61.7(4) . . . . ? C30 C29 N7 O1 -61.1(4) . . . . ? C1 C29 N7 C26 4.1(3) . . . . ? C31 C29 N7 C26 -114.5(3) . . . . ? C30 C29 N7 C26 122.7(3) . . . . ? C2 C1 S1 C4 0.6(2) . . . . ? C29 C1 S1 C4 -177.8(3) . . . . ? C3 C4 S1 C1 -1.0(2) . . . . ? C5 C4 S1 C1 176.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.265 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.044 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 -0.037 0.205 268.2 52.4 2 0.750 -0.044 0.295 268.2 51.6 3 0.250 -0.020 0.705 268.2 52.4 4 0.750 -0.012 0.795 268.2 51.5 _platon_squeeze_details ; ; _vrf_CHEMW03_jmwnt13 ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: The deviation is a result of the application of the SQUEEZE routine from PLATON to account for disordered solvent of crystallisation that could not be reliably modelled by normal techniques. This also results in a number of other alerts. ; _vrf_PLAT043_jmwnt13 ; PROBLEM: Check Reported Molecular Weight ................ 638.80 RESPONSE: See Above. ; _vrf_PLAT041_jmwnt13 ; PROBLEM: Calculated and Reported SunFormula Strings differ ... ? RESPONSE: See Above. ;