# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_nndans _database_code_depnum_ccdc_archive 'CCDC 832284' #TrackingRef '- Compound 4 cif.txt' _audit_creation_date ; 'Tue Feb 01 06:46:28 2011' ; _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _chemical_oxdiff_usercomment 'NNDABS #10116 for CS/AJB, RT, Twinned crystal' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H32 N4 O6 S2' _chemical_formula_sum 'C30 H32 N4 O6 S2' _chemical_formula_weight 608.72 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, y, -z+1/2' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' _cell_length_a 24.0493(16) _cell_length_b 21.2442(13) _cell_length_c 11.3248(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5785.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4744 _cell_measurement_theta_min 2.9926 _cell_measurement_theta_max 28.1385 _exptl_crystal_description tablet _exptl_crystal_colour light_green _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_T_min 0.88561 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_orient_matrix_UB_11 -0.0030786000 _diffrn_orient_matrix_UB_12 0.0315729000 _diffrn_orient_matrix_UB_13 0.0190591000 _diffrn_orient_matrix_UB_21 -0.0290491000 _diffrn_orient_matrix_UB_22 -0.0018424000 _diffrn_orient_matrix_UB_23 -0.0105938000 _diffrn_orient_matrix_UB_31 -0.0042326000 _diffrn_orient_matrix_UB_32 -0.0105829000 _diffrn_orient_matrix_UB_33 0.0587265000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -69.00 30.00 1.0000 112.2900 omega____ theta____ kappa____ phi______ frames - -28.3928 77.0000 -150.0000 99 #__ type_ start__ end____ width___ exp.time_ 2 omega -72.00 39.00 1.0000 112.2900 omega____ theta____ kappa____ phi______ frames - -28.3928 77.0000 90.0000 111 ; _diffrn_measurement_method '\w scans' _reflns_odcompleteness_completeness 98.90 _reflns_odcompleteness_theta 26.32 _reflns_odcompleteness_iscentric 1 _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_detector_area_resol_mean 16.1592 _diffrn_reflns_number 18834 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 28.13 _reflns_number_total 6458 _reflns_number_gt 3289 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0829P)^2^+1.3276P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6458 _refine_ls_number_parameters 383 _refine_ls_number_restraints 389 _refine_ls_R_factor_all 0.1376 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.2199 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.016 _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 0.01946(5) 0.10966(5) 0.80542(9) 0.0616(3) Uani 1 1 d U . . S2 S 0.14966(5) -0.10433(6) 0.77241(9) 0.0670(4) Uani 1 1 d U . . O1 O 0.00795(12) 0.04739(12) 0.7283(2) 0.0624(7) Uani 1 1 d U . . O2 O -0.03176(13) 0.12889(14) 0.8561(3) 0.0799(9) Uani 1 1 d U . . O3 O 0.06425(14) 0.09948(14) 0.8829(2) 0.0806(9) Uani 1 1 d U . . O4 O 0.09493(11) -0.06330(12) 0.7716(2) 0.0619(7) Uani 1 1 d U . . O5 O 0.14172(15) -0.15838(15) 0.7010(2) 0.0868(10) Uani 1 1 d U . . O6 O 0.19231(14) -0.05996(16) 0.7435(2) 0.0860(10) Uani 1 1 d U . . N1 N -0.04176(18) -0.14035(19) 0.7312(3) 0.0764(11) Uani 1 1 d U . . N2 N -0.07526(17) -0.09634(19) 0.7173(3) 0.0752(10) Uani 1 1 d U . . N3 N 0.16067(15) 0.23138(19) 0.3748(3) 0.0734(10) Uani 1 1 d U . . N4 N 0.18643(16) -0.09810(18) 1.3396(3) 0.0752(10) Uani 1 1 d U . . C1 C 0.0154(2) -0.1196(2) 0.6938(4) 0.0686(11) Uani 1 1 d U . . H1 H 0.0366 -0.1540 0.6578 0.082 Uiso 1 1 calc R . . C2 C 0.00340(19) -0.0678(2) 0.6072(3) 0.0683(12) Uani 1 1 d U . . H2A H -0.0059 -0.0837 0.5295 0.082 Uiso 1 1 calc R . . H2B H 0.0338 -0.0379 0.6014 0.082 Uiso 1 1 calc R . . C3 C -0.04689(19) -0.0403(2) 0.6706(3) 0.0678(11) Uani 1 1 d U . . H3 H -0.0707 -0.0153 0.6183 0.081 Uiso 1 1 calc R . . C4 C -0.02676(17) -0.00325(18) 0.7775(3) 0.0591(10) Uani 1 1 d U . . H4 H -0.0588 0.0152 0.8182 0.071 Uiso 1 1 calc R . . C5 C 0.00539(18) -0.04458(19) 0.8628(3) 0.0625(11) Uani 1 1 d U . . H5A H -0.0209 -0.0659 0.9139 0.075 Uiso 1 1 calc R . . H5B H 0.0283 -0.0178 0.9122 0.075 Uiso 1 1 calc R . . C6 C 0.04314(18) -0.09463(18) 0.8039(3) 0.0601(10) Uani 1 1 d U . . H6 H 0.0506 -0.1291 0.8592 0.072 Uiso 1 1 calc R . . C7 C 0.03843(17) 0.15927(17) 0.6888(3) 0.0532(9) Uani 1 1 d U . . C8 C 0.00135(19) 0.20472(19) 0.6593(4) 0.0668(11) Uani 1 1 d U . . H8 H -0.0310 0.2098 0.7032 0.080 Uiso 1 1 calc R . . C9 C 0.0120(2) 0.2437(2) 0.5632(4) 0.0714(12) Uani 1 1 d U . . H9 H -0.0141 0.2739 0.5415 0.086 Uiso 1 1 calc R . . C10 C 0.06001(18) 0.23821(18) 0.5006(4) 0.0626(10) Uani 1 1 d U . . H10 H 0.0663 0.2647 0.4365 0.075 Uiso 1 1 calc R . . C11 C 0.10059(16) 0.19274(17) 0.5316(3) 0.0522(9) Uani 1 1 d U . . C12 C 0.15059(17) 0.18711(19) 0.4648(3) 0.0577(10) Uani 1 1 d U . . C13 C 0.18548(18) 0.1384(2) 0.4894(4) 0.0680(11) Uani 1 1 d U . . H13 H 0.2177 0.1334 0.4450 0.082 Uiso 1 1 calc R . . C14 C 0.17383(18) 0.0960(2) 0.5799(4) 0.0680(11) Uani 1 1 d U . . H14 H 0.1985 0.0632 0.5940 0.082 Uiso 1 1 calc R . . C15 C 0.12799(17) 0.10086(18) 0.6477(3) 0.0574(10) Uani 1 1 d U . . H15 H 0.1217 0.0724 0.7086 0.069 Uiso 1 1 calc R . . C16 C 0.08921(16) 0.15024(16) 0.6249(3) 0.0491(9) Uani 1 1 d U . . C17 C 0.1784(2) 0.2930(2) 0.4174(5) 0.0988(17) Uani 1 1 d U . . H17A H 0.1549 0.3058 0.4817 0.148 Uiso 1 1 calc R . . H17B H 0.1756 0.3232 0.3545 0.148 Uiso 1 1 calc R . . H17C H 0.2162 0.2906 0.4441 0.148 Uiso 1 1 calc R . . C18 C 0.1928(2) 0.2105(3) 0.2738(4) 0.1061(18) Uani 1 1 d U . . H18A H 0.1772 0.1722 0.2435 0.159 Uiso 1 1 calc R . . H18B H 0.2306 0.2033 0.2975 0.159 Uiso 1 1 calc R . . H18C H 0.1919 0.2423 0.2136 0.159 Uiso 1 1 calc R . . C19 C 0.15598(16) -0.12966(19) 0.9194(3) 0.0541(9) Uani 1 1 d U . . C20 C 0.15877(19) -0.1938(2) 0.9376(3) 0.0676(11) Uani 1 1 d U . . H20 H 0.1528 -0.2214 0.8752 0.081 Uiso 1 1 calc R . . C21 C 0.1706(2) -0.2170(2) 1.0498(4) 0.0774(13) Uani 1 1 d U . . H21 H 0.1737 -0.2601 1.0616 0.093 Uiso 1 1 calc R . . C22 C 0.17747(18) -0.1772(2) 1.1414(4) 0.0658(11) Uani 1 1 d U . . H22 H 0.1859 -0.1934 1.2155 0.079 Uiso 1 1 calc R . . C23 C 0.17218(15) -0.11149(18) 1.1275(3) 0.0515(9) Uani 1 1 d U . . C24 C 0.17894(16) -0.0704(2) 1.2261(3) 0.0585(10) Uani 1 1 d U . . C25 C 0.17849(19) -0.0073(2) 1.2069(4) 0.0687(12) Uani 1 1 d U . . H25 H 0.1851 0.0197 1.2699 0.082 Uiso 1 1 calc R . . C26 C 0.16838(19) 0.0179(2) 1.0961(4) 0.0698(12) Uani 1 1 d U . . H26 H 0.1676 0.0614 1.0867 0.084 Uiso 1 1 calc R . . C27 C 0.15957(17) -0.01986(18) 1.0007(4) 0.0607(10) Uani 1 1 d U . . H27 H 0.1518 -0.0023 0.9273 0.073 Uiso 1 1 calc R . . C28 C 0.16235(14) -0.08612(17) 1.0138(3) 0.0478(8) Uani 1 1 d U . . C29 C 0.2184(3) -0.0616(3) 1.4226(5) 0.141(3) Uani 1 1 d U . . H29A H 0.2524 -0.0482 1.3860 0.211 Uiso 1 1 calc R . . H29B H 0.2269 -0.0870 1.4905 0.211 Uiso 1 1 calc R . . H29C H 0.1974 -0.0254 1.4466 0.211 Uiso 1 1 calc R . . C30 C 0.1359(2) -0.1214(3) 1.3896(4) 0.0964(17) Uani 1 1 d U . . H30A H 0.1157 -0.1446 1.3309 0.145 Uiso 1 1 calc R . . H30B H 0.1136 -0.0867 1.4165 0.145 Uiso 1 1 calc R . . H30C H 0.1443 -0.1485 1.4551 0.145 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 S1 0.0746(7) 0.0570(6) 0.0533(6) -0.0074(5) 0.0107(5) -0.0100(5) S2 0.0775(8) 0.0840(8) 0.0396(5) -0.0015(5) 0.0002(5) 0.0108(6) O1 0.0752(19) 0.0548(15) 0.0574(15) -0.0065(13) 0.0179(13) -0.0142(14) O2 0.091(2) 0.0708(19) 0.078(2) -0.0199(16) 0.0345(17) -0.0066(16) O3 0.094(2) 0.095(2) 0.0523(17) 0.0041(15) -0.0024(16) -0.0215(18) O4 0.0666(18) 0.0658(17) 0.0533(15) 0.0055(13) -0.0093(13) -0.0017(14) O5 0.117(3) 0.098(2) 0.0450(15) -0.0204(16) -0.0090(16) 0.024(2) O6 0.082(2) 0.119(3) 0.0570(18) 0.0193(17) 0.0186(15) -0.011(2) N1 0.088(3) 0.075(3) 0.065(2) -0.005(2) -0.014(2) -0.019(2) N2 0.077(3) 0.070(2) 0.079(2) -0.004(2) -0.012(2) -0.023(2) N3 0.073(2) 0.088(3) 0.059(2) 0.0175(19) -0.0029(18) -0.019(2) N4 0.080(3) 0.106(3) 0.0393(18) -0.0009(18) -0.0134(17) 0.004(2) C1 0.085(3) 0.062(3) 0.059(2) -0.012(2) -0.012(2) 0.006(2) C2 0.087(3) 0.083(3) 0.0342(19) -0.0057(19) -0.0081(19) -0.004(2) C3 0.083(3) 0.067(3) 0.053(2) 0.004(2) -0.016(2) -0.009(2) C4 0.064(3) 0.060(2) 0.053(2) -0.0130(19) 0.0006(18) -0.005(2) C5 0.083(3) 0.072(3) 0.0329(19) -0.0029(18) -0.0014(18) -0.012(2) C6 0.080(3) 0.056(2) 0.043(2) 0.0052(18) -0.0107(19) -0.015(2) C7 0.064(2) 0.042(2) 0.054(2) -0.0078(17) 0.0005(18) -0.0088(18) C8 0.071(3) 0.051(2) 0.077(3) -0.014(2) 0.013(2) 0.003(2) C9 0.085(3) 0.055(3) 0.075(3) -0.003(2) -0.004(2) 0.014(2) C10 0.075(3) 0.055(2) 0.058(2) 0.0037(19) -0.010(2) 0.003(2) C11 0.064(2) 0.048(2) 0.0452(19) 0.0004(16) -0.0125(17) -0.0088(18) C12 0.059(2) 0.069(3) 0.045(2) 0.0067(18) -0.0049(17) -0.012(2) C13 0.055(2) 0.087(3) 0.062(2) 0.005(2) 0.0055(19) -0.006(2) C14 0.060(3) 0.073(3) 0.070(3) 0.009(2) -0.005(2) 0.011(2) C15 0.059(2) 0.058(2) 0.056(2) 0.0043(18) -0.0019(18) 0.000(2) C16 0.058(2) 0.0420(19) 0.0469(19) 0.0007(16) -0.0074(16) -0.0081(17) C17 0.110(4) 0.089(4) 0.098(4) 0.033(3) -0.020(3) -0.033(3) C18 0.111(4) 0.149(5) 0.058(3) 0.020(3) 0.016(3) -0.020(4) C19 0.056(2) 0.064(2) 0.0418(19) 0.0041(17) 0.0011(16) 0.0041(19) C20 0.088(3) 0.062(3) 0.053(2) -0.010(2) -0.005(2) 0.000(2) C21 0.110(4) 0.055(3) 0.067(3) 0.008(2) 0.002(3) 0.007(2) C22 0.085(3) 0.065(3) 0.047(2) 0.006(2) -0.002(2) 0.008(2) C23 0.046(2) 0.062(2) 0.046(2) 0.0030(17) 0.0004(15) 0.0002(18) C24 0.052(2) 0.078(3) 0.045(2) -0.003(2) -0.0009(16) -0.002(2) C25 0.074(3) 0.079(3) 0.053(2) -0.017(2) 0.005(2) -0.010(2) C26 0.085(3) 0.058(2) 0.067(3) -0.007(2) 0.014(2) -0.008(2) C27 0.069(3) 0.060(2) 0.053(2) 0.0108(19) 0.0064(19) 0.002(2) C28 0.049(2) 0.054(2) 0.0409(18) 0.0019(16) 0.0052(15) 0.0014(17) C29 0.175(7) 0.179(6) 0.068(4) -0.008(4) -0.055(4) -0.038(5) C30 0.111(4) 0.119(4) 0.059(3) 0.037(3) 0.010(3) 0.017(3) _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 O3 1.406(3) . ? S1 O2 1.419(3) . ? S1 O1 1.609(3) . ? S1 C7 1.750(4) . ? S2 O5 1.417(3) . ? S2 O6 1.431(3) . ? S2 O4 1.579(3) . ? S2 C19 1.756(4) . ? O1 C4 1.471(4) . ? O4 C6 1.459(5) . ? N1 N2 1.244(5) . ? N1 C1 1.504(6) . ? N2 C3 1.470(5) . ? N3 C12 1.409(5) . ? N3 C18 1.449(6) . ? N3 C17 1.459(6) . ? N4 C24 1.425(5) . ? N4 C30 1.430(6) . ? N4 C29 1.441(6) . ? C1 C2 1.503(6) . ? C1 C6 1.511(5) . ? C1 H1 0.9800 . ? C2 C3 1.522(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.523(5) . ? C3 H3 0.9800 . ? C4 C5 1.518(5) . ? C4 H4 0.9800 . ? C5 C6 1.549(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6 0.9800 . ? C7 C8 1.356(5) . ? C7 C16 1.432(5) . ? C8 C9 1.392(6) . ? C8 H8 0.9300 . ? C9 C10 1.361(6) . ? C9 H9 0.9300 . ? C10 C11 1.417(5) . ? C10 H10 0.9300 . ? C11 C16 1.417(5) . ? C11 C12 1.425(5) . ? C12 C13 1.361(6) . ? C13 C14 1.393(5) . ? C13 H13 0.9300 . ? C14 C15 1.347(5) . ? C14 H14 0.9300 . ? C15 C16 1.427(5) . ? C15 H15 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.379(5) . ? C19 C28 1.423(5) . ? C20 C21 1.392(5) . ? C20 H20 0.9300 . ? C21 C22 1.349(6) . ? C21 H21 0.9300 . ? C22 C23 1.410(5) . ? C22 H22 0.9300 . ? C23 C28 1.415(5) . ? C23 C24 1.427(5) . ? C24 C25 1.356(5) . ? C25 C26 1.386(6) . ? C25 H25 0.9300 . ? C26 C27 1.362(5) . ? C26 H26 0.9300 . ? C27 C28 1.417(5) . ? C27 H27 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 O3 S1 O2 117.20(19) . . ? O3 S1 O1 110.12(18) . . ? O2 S1 O1 107.88(17) . . ? O3 S1 C7 111.32(19) . . ? O2 S1 C7 111.0(2) . . ? O1 S1 C7 97.49(15) . . ? O5 S2 O6 120.0(2) . . ? O5 S2 O4 109.37(18) . . ? O6 S2 O4 103.45(18) . . ? O5 S2 C19 107.69(19) . . ? O6 S2 C19 110.91(19) . . ? O4 S2 C19 104.30(17) . . ? C4 O1 S1 119.5(2) . . ? C6 O4 S2 117.3(2) . . ? N2 N1 C1 109.6(4) . . ? N1 N2 C3 110.7(4) . . ? C12 N3 C18 117.3(4) . . ? C12 N3 C17 114.2(3) . . ? C18 N3 C17 112.3(4) . . ? C24 N4 C30 113.1(3) . . ? C24 N4 C29 115.7(4) . . ? C30 N4 C29 112.5(4) . . ? C2 C1 N1 102.9(4) . . ? C2 C1 C6 111.4(3) . . ? N1 C1 C6 105.9(3) . . ? C2 C1 H1 112.0 . . ? N1 C1 H1 112.0 . . ? C6 C1 H1 112.0 . . ? C1 C2 C3 97.2(3) . . ? C1 C2 H2A 112.3 . . ? C3 C2 H2A 112.3 . . ? C1 C2 H2B 112.3 . . ? C3 C2 H2B 112.3 . . ? H2A C2 H2B 109.9 . . ? N2 C3 C4 106.3(3) . . ? N2 C3 C2 103.2(4) . . ? C4 C3 C2 108.7(4) . . ? N2 C3 H3 112.7 . . ? C4 C3 H3 112.7 . . ? C2 C3 H3 112.7 . . ? O1 C4 C5 112.0(3) . . ? O1 C4 C3 104.9(3) . . ? C5 C4 C3 111.7(3) . . ? O1 C4 H4 109.4 . . ? C5 C4 H4 109.4 . . ? C3 C4 H4 109.4 . . ? C4 C5 C6 114.9(3) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? O4 C6 C1 109.3(3) . . ? O4 C6 C5 107.2(3) . . ? C1 C6 C5 109.8(4) . . ? O4 C6 H6 110.2 . . ? C1 C6 H6 110.2 . . ? C5 C6 H6 110.2 . . ? C8 C7 C16 122.1(4) . . ? C8 C7 S1 116.3(3) . . ? C16 C7 S1 121.5(3) . . ? C7 C8 C9 119.7(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.8(4) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.9(4) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C16 119.1(4) . . ? C10 C11 C12 120.5(3) . . ? C16 C11 C12 120.3(3) . . ? C13 C12 N3 123.3(4) . . ? C13 C12 C11 118.4(3) . . ? N3 C12 C11 118.2(4) . . ? C12 C13 C14 121.2(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 122.3(4) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 118.5(4) . . ? C11 C16 C7 117.1(3) . . ? C15 C16 C7 124.4(3) . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C28 121.6(3) . . ? C20 C19 S2 116.7(3) . . ? C28 C19 S2 121.5(3) . . ? C19 C20 C21 119.7(4) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.4(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 121.6(4) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C22 C23 C28 119.6(3) . . ? C22 C23 C24 120.5(3) . . ? C28 C23 C24 119.8(3) . . ? C25 C24 N4 123.6(4) . . ? C25 C24 C23 118.6(3) . . ? N4 C24 C23 117.8(4) . . ? C24 C25 C26 121.9(4) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C27 C26 C25 121.2(4) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 119.6(4) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C23 C28 C27 118.8(3) . . ? C23 C28 C19 117.0(3) . . ? C27 C28 C19 124.2(3) . . ? N4 C29 H29A 109.5 . . ? N4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N4 C30 H30A 109.5 . . ? N4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 O3 S1 O1 C4 84.1(3) . . . . ? O2 S1 O1 C4 -44.9(3) . . . . ? C7 S1 O1 C4 -159.8(3) . . . . ? O5 S2 O4 C6 53.9(3) . . . . ? O6 S2 O4 C6 -177.1(2) . . . . ? C19 S2 O4 C6 -61.0(3) . . . . ? C1 N1 N2 C3 -0.5(5) . . . . ? N2 N1 C1 C2 -24.9(4) . . . . ? N2 N1 C1 C6 92.2(4) . . . . ? N1 C1 C2 C3 36.8(4) . . . . ? C6 C1 C2 C3 -76.3(4) . . . . ? N1 N2 C3 C4 -88.9(4) . . . . ? N1 N2 C3 C2 25.4(4) . . . . ? C1 C2 C3 N2 -37.4(4) . . . . ? C1 C2 C3 C4 75.2(4) . . . . ? S1 O1 C4 C5 -79.8(4) . . . . ? S1 O1 C4 C3 158.9(3) . . . . ? N2 C3 C4 O1 172.3(3) . . . . ? C2 C3 C4 O1 61.8(4) . . . . ? N2 C3 C4 C5 50.7(5) . . . . ? C2 C3 C4 C5 -59.7(4) . . . . ? O1 C4 C5 C6 -79.6(4) . . . . ? C3 C4 C5 C6 37.8(5) . . . . ? S2 O4 C6 C1 -91.9(3) . . . . ? S2 O4 C6 C5 149.2(2) . . . . ? C2 C1 C6 O4 -58.8(5) . . . . ? N1 C1 C6 O4 -170.0(3) . . . . ? C2 C1 C6 C5 58.5(5) . . . . ? N1 C1 C6 C5 -52.7(4) . . . . ? C4 C5 C6 O4 82.5(4) . . . . ? C4 C5 C6 C1 -36.1(5) . . . . ? O3 S1 C7 C8 -136.5(3) . . . . ? O2 S1 C7 C8 -4.0(4) . . . . ? O1 S1 C7 C8 108.4(3) . . . . ? O3 S1 C7 C16 46.3(3) . . . . ? O2 S1 C7 C16 178.7(3) . . . . ? O1 S1 C7 C16 -68.8(3) . . . . ? C16 C7 C8 C9 0.9(6) . . . . ? S1 C7 C8 C9 -176.3(3) . . . . ? C7 C8 C9 C10 -2.2(6) . . . . ? C8 C9 C10 C11 -0.1(6) . . . . ? C9 C10 C11 C16 3.7(6) . . . . ? C9 C10 C11 C12 179.6(4) . . . . ? C18 N3 C12 C13 28.6(6) . . . . ? C17 N3 C12 C13 -105.9(5) . . . . ? C18 N3 C12 C11 -149.8(4) . . . . ? C17 N3 C12 C11 75.7(5) . . . . ? C10 C11 C12 C13 -172.8(4) . . . . ? C16 C11 C12 C13 3.0(5) . . . . ? C10 C11 C12 N3 5.6(5) . . . . ? C16 C11 C12 N3 -178.5(3) . . . . ? N3 C12 C13 C14 179.7(4) . . . . ? C11 C12 C13 C14 -2.0(6) . . . . ? C12 C13 C14 C15 -0.3(7) . . . . ? C13 C14 C15 C16 1.4(6) . . . . ? C10 C11 C16 C15 174.0(3) . . . . ? C12 C11 C16 C15 -2.0(5) . . . . ? C10 C11 C16 C7 -4.7(5) . . . . ? C12 C11 C16 C7 179.3(3) . . . . ? C14 C15 C16 C11 -0.3(5) . . . . ? C14 C15 C16 C7 178.3(4) . . . . ? C8 C7 C16 C11 2.6(5) . . . . ? S1 C7 C16 C11 179.6(3) . . . . ? C8 C7 C16 C15 -176.1(4) . . . . ? S1 C7 C16 C15 1.0(5) . . . . ? O5 S2 C19 C20 7.2(4) . . . . ? O6 S2 C19 C20 -125.9(3) . . . . ? O4 S2 C19 C20 123.3(3) . . . . ? O5 S2 C19 C28 -177.7(3) . . . . ? O6 S2 C19 C28 49.2(4) . . . . ? O4 S2 C19 C28 -61.5(3) . . . . ? C28 C19 C20 C21 -2.9(6) . . . . ? S2 C19 C20 C21 172.2(4) . . . . ? C19 C20 C21 C22 2.2(7) . . . . ? C20 C21 C22 C23 1.0(7) . . . . ? C21 C22 C23 C28 -3.4(6) . . . . ? C21 C22 C23 C24 179.1(4) . . . . ? C30 N4 C24 C25 103.7(5) . . . . ? C29 N4 C24 C25 -28.1(7) . . . . ? C30 N4 C24 C23 -77.1(5) . . . . ? C29 N4 C24 C23 151.1(5) . . . . ? C22 C23 C24 C25 174.1(4) . . . . ? C28 C23 C24 C25 -3.3(6) . . . . ? C22 C23 C24 N4 -5.2(6) . . . . ? C28 C23 C24 N4 177.4(3) . . . . ? N4 C24 C25 C26 -176.8(4) . . . . ? C23 C24 C25 C26 3.9(6) . . . . ? C24 C25 C26 C27 -1.4(7) . . . . ? C25 C26 C27 C28 -1.9(7) . . . . ? C22 C23 C28 C27 -177.3(4) . . . . ? C24 C23 C28 C27 0.2(5) . . . . ? C22 C23 C28 C19 2.6(5) . . . . ? C24 C23 C28 C19 -180.0(3) . . . . ? C26 C27 C28 C23 2.4(6) . . . . ? C26 C27 C28 C19 -177.5(4) . . . . ? C20 C19 C28 C23 0.5(5) . . . . ? S2 C19 C28 C23 -174.4(3) . . . . ? C20 C19 C28 C27 -179.6(4) . . . . ? S2 C19 C28 C27 5.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.740 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.051 # start Validation Reply Form _vrf_PLAT230_ALERT_2_B ; PROBLEM: Hirshfeld Test Diff for S2 -- O6 .. 7.5 su RESPONSE: Every specimen crystal examined was twinned. The one chosen for data collection had a sufficiently low fraction of the minor component that twin refinement did not make a significant improvement and was deemed unnecessary. However, 25 of the 30 _most disagreeable_ reflections listed by SHELXL have F(obs) > F(calc), and four reflections had to be omitted because the discrepancy was so large. The ADPs may be affected by this small amount of twinning, influencing the Hirshfeld tests. ; _vrf_PLAT094_ALERT_2_C ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.10 RESPONSE: The largest peak in the difference electron density map (0.74 e/Ang**3) could be interpreted as an alternative site for a disordered O1, but this explanation is rejected because no credible alternative peaks appear for the other O atoms attached to S1. Therefore this peak is ascribed to the aforementioned twinning. ; _vrf_PLAT340_ALERT_3_C ; PROBLEM: Low Bond Precision on C-C Bonds (x 1000) Ang .. 6 RESPONSE: Given the quality of the crystalline material, the data set reported here is the best available. The main point of interest is the relative orientation of the dansyl substituents, not fine differences in bond distances. ; # end Validation Reply Form