# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2013 ####################################################################### # # 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_eusna #TrackingRef 'web_deposit_cif_file_0_GianlucaCroce_1363080901.eusna.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 N2 Na O6 S' _chemical_formula_weight 343.26 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' Na Na 0.0362 0.0249 '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' 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 11.116(0) _cell_length_b 5.810(0) _cell_length_c 46.919(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3030.22(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_T_min 0.94578 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 ? _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 44762 _diffrn_reflns_av_R_equivalents 0.2272 _diffrn_reflns_av_sigmaI/netI 0.3020 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -67 _diffrn_reflns_limit_l_max 67 _diffrn_reflns_theta_min 4.1234 _diffrn_reflns_theta_max 30.5254 _reflns_number_total 4401 _reflns_number_gt 1810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_cell_refinement 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_data_reduction 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_structure_solution 'Sir2008 (Burla, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2007)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, L. J., 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^)+(0.0256P)^2^+23.3944P] 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 4401 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2403 _refine_ls_R_factor_gt 0.1192 _refine_ls_wR_factor_ref 0.2497 _refine_ls_wR_factor_gt 0.2176 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.44202(16) 0.1230(3) 0.04106(3) 0.0336(4) Uani 1 1 d . . . Na1 Na 0.1468(3) 0.1427(5) 0.00911(6) 0.0456(8) Uani 1 1 d . . . O1 O 0.4736(4) 0.3187(7) 0.02349(9) 0.0354(11) Uani 1 1 d . . . C1 C 0.3579(6) 0.0986(11) 0.09535(13) 0.0316(15) Uani 1 1 d . . . H1 H 0.3176 -0.0330 0.0893 0.038 Uiso 1 1 calc R . . O2 O 0.3315(5) 0.0126(9) 0.03308(9) 0.0471(14) Uani 1 1 d . . . C2 C 0.4875(6) 0.4221(9) 0.08348(13) 0.0278(14) Uani 1 1 d . . . H2 H 0.5311 0.5067 0.0702 0.033 Uiso 1 1 calc R . . C3 C 0.4251(6) 0.2293(10) 0.07611(13) 0.0266(14) Uani 1 1 d . . . O3 O 0.5398(5) -0.0417(9) 0.04260(11) 0.0599(16) Uani 1 1 d . . . N2 N 0.4282(5) 0.4587(9) 0.15843(11) 0.0352(13) Uani 1 1 d . . . N3 N 0.5372(5) 0.6646(9) 0.12700(11) 0.0380(14) Uani 1 1 d . . . C5 C 0.5005(6) 0.6407(12) 0.15451(14) 0.0363(16) Uani 1 1 d . . . C6 C 0.4817(6) 0.4856(11) 0.11244(13) 0.0310(15) Uani 1 1 d . . . C7 C 0.4160(6) 0.3579(13) 0.13177(13) 0.0342(15) Uani 1 1 d . . . C8 C 0.5989(7) 0.9957(13) 0.17141(17) 0.049(2) Uani 1 1 d . . . H8 H 0.6071 1.0442 0.1526 0.059 Uiso 1 1 calc R . . C9 C 0.3522(6) 0.1682(12) 0.12358(13) 0.0343(16) Uani 1 1 d . . . H9 H 0.3059 0.0872 0.1367 0.041 Uiso 1 1 calc R . . O4 O 0.2878(6) 0.3137(16) 0.20497(13) 0.113(3) Uani 1 1 d . . . C11 C 0.5748(8) 0.8548(15) 0.22735(16) 0.058(2) Uani 1 1 d . . . H11 H 0.5669 0.8069 0.2462 0.070 Uiso 1 1 calc R . . C12 C 0.5320(7) 0.7198(14) 0.20569(15) 0.049(2) Uani 1 1 d . . . H12 H 0.4944 0.5810 0.2099 0.058 Uiso 1 1 calc R . . C13 C 0.6414(7) 1.1303(14) 0.19338(17) 0.053(2) Uani 1 1 d . . . H13 H 0.6785 1.2698 0.1892 0.064 Uiso 1 1 calc R . . C14 C 0.6298(7) 1.0623(15) 0.22124(17) 0.055(2) Uani 1 1 d . . . H14 H 0.6587 1.1550 0.2359 0.066 Uiso 1 1 calc R . . C15 C 0.5444(6) 0.7890(12) 0.17747(14) 0.0376(17) Uani 1 1 d . . . O5 O 0.6943(6) 0.9352(14) 0.09334(14) 0.097(2) Uani 1 1 d . . . O6 O 0.2171(5) -0.1524(11) -0.02441(11) 0.0679(17) 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 0.0439(9) 0.0280(7) 0.0289(8) -0.0078(8) 0.0018(8) -0.0002(8) Na1 0.0514(18) 0.0342(15) 0.0512(18) -0.0044(14) -0.0044(14) -0.0082(15) O1 0.057(3) 0.019(2) 0.030(2) 0.0004(19) 0.004(2) -0.005(2) C1 0.033(4) 0.027(3) 0.035(4) 0.001(3) 0.000(3) -0.007(3) O2 0.062(3) 0.047(3) 0.032(3) -0.008(2) -0.003(2) -0.020(3) C2 0.037(4) 0.012(3) 0.034(4) 0.000(2) 0.003(3) -0.011(3) C3 0.026(3) 0.025(3) 0.029(3) -0.003(3) -0.002(3) 0.001(3) O3 0.079(4) 0.057(3) 0.043(3) -0.001(3) 0.014(3) 0.035(3) N2 0.042(3) 0.035(3) 0.028(3) -0.008(2) -0.004(3) 0.004(3) N3 0.055(4) 0.029(3) 0.030(3) -0.008(3) -0.002(3) -0.007(3) C5 0.042(4) 0.032(3) 0.035(4) -0.004(3) -0.009(3) 0.002(3) C6 0.033(4) 0.031(3) 0.029(4) -0.005(3) -0.005(3) 0.002(3) C7 0.032(4) 0.044(4) 0.027(3) -0.009(3) -0.003(3) -0.007(3) C8 0.066(5) 0.038(4) 0.044(5) -0.013(4) -0.010(4) 0.006(4) C9 0.039(4) 0.036(4) 0.028(4) 0.001(3) 0.004(3) -0.011(3) O4 0.102(6) 0.176(9) 0.060(4) 0.014(5) 0.015(4) -0.025(6) C11 0.075(6) 0.065(5) 0.035(4) -0.029(4) -0.002(4) -0.006(5) C12 0.061(5) 0.052(5) 0.033(4) -0.009(4) -0.002(4) 0.000(4) C13 0.060(5) 0.039(4) 0.061(5) -0.017(4) -0.006(4) 0.007(4) C14 0.055(5) 0.063(6) 0.047(5) -0.036(4) -0.006(4) 0.002(4) C15 0.045(4) 0.038(4) 0.030(4) -0.013(3) -0.011(3) 0.002(4) O5 0.073(5) 0.126(7) 0.093(5) 0.000(5) 0.012(4) -0.012(5) O6 0.062(4) 0.081(4) 0.060(3) -0.010(4) 0.001(3) -0.003(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 S1 O2 1.436(5) . ? S1 O1 1.448(4) . ? S1 O3 1.450(5) . ? S1 C3 1.767(6) . ? S1 Na1 3.318(3) 7_655 ? Na1 O1 2.406(5) 7_655 ? Na1 O2 2.437(6) 7_665 ? Na1 O6 2.455(7) . ? Na1 O2 2.460(6) . ? Na1 O1 2.469(5) 3_455 ? Na1 O6 2.486(7) 7_665 ? Na1 S1 3.318(3) 7_665 ? Na1 Na1 3.702(4) 7_665 ? Na1 Na1 3.702(4) 7_655 ? Na1 Na1 3.759(5) 5 ? O1 Na1 2.406(5) 7_665 ? O1 Na1 2.469(5) 3 ? C1 C9 1.386(8) . ? C1 C3 1.396(8) . ? O2 Na1 2.437(6) 7_655 ? C2 C3 1.362(8) . ? C2 C6 1.409(8) . ? N2 C5 1.341(9) . ? N2 C7 1.388(8) . ? N3 C5 1.361(8) . ? N3 C6 1.389(8) . ? C5 C15 1.463(9) . ? C6 C7 1.381(9) . ? C7 C9 1.366(9) . ? C8 C15 1.375(10) . ? C8 C13 1.377(10) . ? C11 C12 1.369(9) . ? C11 C14 1.382(11) . ? C12 C15 1.391(10) . ? C13 C14 1.372(11) . ? O6 Na1 2.486(7) 7_655 ? 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 114.2(3) . . ? O2 S1 O3 111.1(3) . . ? O1 S1 O3 111.4(3) . . ? O2 S1 C3 107.9(3) . . ? O1 S1 C3 106.3(3) . . ? O3 S1 C3 105.3(3) . . ? O2 S1 Na1 41.6(2) . 7_655 ? O1 S1 Na1 118.41(19) . 7_655 ? O3 S1 Na1 72.0(3) . 7_655 ? C3 S1 Na1 133.1(2) . 7_655 ? O1 Na1 O2 127.98(19) 7_655 7_665 ? O1 Na1 O6 79.07(18) 7_655 . ? O2 Na1 O6 151.6(2) 7_665 . ? O1 Na1 O2 95.49(18) 7_655 . ? O2 Na1 O2 88.70(17) 7_665 . ? O6 Na1 O2 79.19(19) . . ? O1 Na1 O1 79.10(17) 7_655 3_455 ? O2 Na1 O1 106.45(18) 7_665 3_455 ? O6 Na1 O1 85.10(19) . 3_455 ? O2 Na1 O1 164.1(2) . 3_455 ? O1 Na1 O6 152.9(2) 7_655 7_665 ? O2 Na1 O6 79.01(19) 7_665 7_665 ? O6 Na1 O6 74.65(16) . 7_665 ? O2 Na1 O6 85.90(19) . 7_665 ? O1 Na1 O6 92.23(19) 3_455 7_665 ? O1 Na1 S1 111.45(14) 7_655 7_665 ? O2 Na1 S1 23.01(12) 7_665 7_665 ? O6 Na1 S1 166.36(19) . 7_665 ? O2 Na1 S1 107.48(14) . 7_665 ? O1 Na1 S1 88.37(13) 3_455 7_665 ? O6 Na1 S1 93.68(16) 7_665 7_665 ? O1 Na1 Na1 163.47(12) 7_655 7_665 ? O2 Na1 Na1 41.12(12) 7_665 7_665 ? O6 Na1 Na1 110.54(17) . 7_665 ? O2 Na1 Na1 73.98(15) . 7_665 ? O1 Na1 Na1 114.33(12) 3_455 7_665 ? O6 Na1 Na1 41.15(15) 7_665 7_665 ? S1 Na1 Na1 61.60(4) 7_665 7_665 ? O1 Na1 Na1 74.39(11) 7_655 7_655 ? O2 Na1 Na1 129.09(16) 7_665 7_655 ? O6 Na1 Na1 41.79(15) . 7_655 ? O2 Na1 Na1 40.67(14) . 7_655 ? O1 Na1 Na1 123.67(12) 3_455 7_655 ? O6 Na1 Na1 89.92(18) 7_665 7_655 ? S1 Na1 Na1 147.62(8) 7_665 7_655 ? Na1 Na1 Na1 103.40(14) 7_665 7_655 ? O1 Na1 Na1 40.16(12) 7_655 5 ? O2 Na1 Na1 125.44(18) 7_665 5 ? O6 Na1 Na1 79.78(16) . 5 ? O2 Na1 Na1 133.87(18) . 5 ? O1 Na1 Na1 38.94(11) 3_455 5 ? O6 Na1 Na1 126.55(19) 7_665 5 ? S1 Na1 Na1 102.44(12) 7_665 5 ? Na1 Na1 Na1 152.15(12) 7_665 5 ? Na1 Na1 Na1 101.07(8) 7_655 5 ? S1 O1 Na1 129.7(3) . 7_665 ? S1 O1 Na1 127.8(3) . 3 ? Na1 O1 Na1 100.90(17) 7_665 3 ? C9 C1 C3 118.9(6) . . ? S1 O2 Na1 115.4(3) . 7_655 ? S1 O2 Na1 134.1(3) . . ? Na1 O2 Na1 98.21(19) 7_655 . ? C3 C2 C6 115.9(6) . . ? C2 C3 C1 123.7(6) . . ? C2 C3 S1 118.0(5) . . ? C1 C3 S1 118.0(5) . . ? C5 N2 C7 105.5(5) . . ? C5 N3 C6 104.9(6) . . ? N2 C5 N3 113.0(6) . . ? N2 C5 C15 124.3(6) . . ? N3 C5 C15 122.5(7) . . ? C7 C6 N3 108.3(5) . . ? C7 C6 C2 121.1(6) . . ? N3 C6 C2 130.5(6) . . ? C9 C7 C6 121.6(6) . . ? C9 C7 N2 130.2(6) . . ? C6 C7 N2 108.3(6) . . ? C15 C8 C13 119.5(8) . . ? C7 C9 C1 118.7(6) . . ? C12 C11 C14 120.0(8) . . ? C11 C12 C15 120.5(8) . . ? C14 C13 C8 121.2(8) . . ? C13 C14 C11 119.4(7) . . ? C8 C15 C12 119.5(7) . . ? C8 C15 C5 120.6(7) . . ? C12 C15 C5 119.9(7) . . ? Na1 O6 Na1 97.1(2) . 7_655 ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.436 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 928876' ####################################################################### # # 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_glicna3 #TrackingRef 'web_deposit_cif_file_1_GianlucaCroce_1363080901.BUONO.glicna3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N3 Na O3 S' _chemical_formula_weight 345.39 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' Na Na 0.0362 0.0249 '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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.4283(10) _cell_length_b 9.8446(3) _cell_length_c 12.3063(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.738(7) _cell_angle_gamma 90.00 _cell_volume 1759.32(12) _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 colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_T_min 0.81093 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 ? _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 25394 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 30.34 _reflns_number_total 4888 _reflns_number_gt 3416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_cell_refinement 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_data_reduction 'CrysAlisPRO 171.34.44(OXford Diffraction)' _computing_structure_solution 'Sir2008 (Burla, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2007)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, L. J., 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^)+(0.0929P)^2^+1.2252P] 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 4888 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1828 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.88523(4) 0.16397(5) 0.21485(4) 0.03664(17) Uani 1 1 d . . . Na1 Na 1.00534(7) 0.39303(9) 0.37601(7) 0.0412(2) Uani 1 1 d . . . O1 O 1.01693(14) 0.61409(15) 0.44619(14) 0.0434(4) Uani 1 1 d . . . O2 O 0.91306(13) 0.02197(16) 0.22677(13) 0.0451(4) Uani 1 1 d . . . N100 N 1.10599(14) 0.2854(2) 0.02111(17) 0.0402(4) Uani 1 1 d . . . O100 O 0.86989(14) 0.2208(2) 0.31526(15) 0.0521(5) Uani 1 1 d . . . N2 N 1.05599(15) 0.3152(2) 0.09510(18) 0.0451(5) Uani 1 1 d . . . H2 H 1.0634 0.3915 0.1311 0.054 Uiso 1 1 calc R . . N3 N 0.95431(14) 0.26298(18) 0.18532(16) 0.0369(4) Uani 1 1 d . . . C2 C 0.99625(16) 0.2219(2) 0.10858(17) 0.0335(4) Uani 1 1 d . . . C3 C 0.77714(18) 0.1654(2) 0.1026(2) 0.0429(5) Uani 1 1 d . . . C4 C 0.87495(19) 0.5918(3) 0.0344(2) 0.0485(6) Uani 1 1 d . . . H4A H 0.9303 0.5570 0.0921 0.058 Uiso 1 1 calc R . . H4B H 0.8477 0.5211 -0.0217 0.058 Uiso 1 1 calc R . . C5 C 0.8059(2) 0.6462(3) 0.0902(3) 0.0566(7) Uani 1 1 d . . . H5 H 0.8386 0.6771 0.1691 0.068 Uiso 1 1 calc R . . C6 C 0.8040(2) 0.7747(3) -0.0796(3) 0.0607(7) Uani 1 1 d . . . H6A H 0.7697 0.7228 -0.1475 0.073 Uiso 1 1 calc R . . H6B H 0.8097 0.8678 -0.1021 0.073 Uiso 1 1 calc R . . C7 C 0.7691(2) 0.1751(4) -0.0115(3) 0.0685(9) Uani 1 1 d . . . H7 H 0.8216 0.1862 -0.0318 0.082 Uiso 1 1 calc R . . C8 C 0.7296(3) 0.5488(5) 0.0888(4) 0.0945(13) Uani 1 1 d . . . H8A H 0.7101 0.5629 0.1551 0.113 Uiso 1 1 calc R . . H8B H 0.7490 0.4552 0.0881 0.113 Uiso 1 1 calc R . . C9 C 0.6847(3) 0.1687(5) -0.0954(3) 0.0887(13) Uani 1 1 d . . . H9 H 0.6810 0.1730 -0.1724 0.106 Uiso 1 1 calc R . . C10 C 0.6991(2) 0.1461(5) 0.1304(3) 0.0823(12) Uani 1 1 d . . . H10 H 0.7034 0.1357 0.2072 0.099 Uiso 1 1 calc R . . C11 C 0.7578(2) 0.7681(3) 0.0127(3) 0.0638(8) Uani 1 1 d . . . H11 H 0.7691 0.8522 0.0579 0.077 Uiso 1 1 calc R . . C12 C 0.6063(3) 0.1563(6) -0.0705(4) 0.1016(15) Uani 1 1 d . . . C13 C 0.6144(3) 0.1424(7) 0.0444(5) 0.118(2) Uani 1 1 d . . . H13 H 0.5617 0.1302 0.0639 0.142 Uiso 1 1 calc R . . C14 C 0.6518(4) 0.5852(7) -0.0246(7) 0.141(2) Uani 1 1 d . . . H14A H 0.6619 0.5422 -0.0902 0.170 Uiso 1 1 calc R . . H14B H 0.5924 0.5570 -0.0218 0.170 Uiso 1 1 calc R . . C15 C 0.6569(3) 0.7368(6) -0.0322(5) 0.1108(17) Uani 1 1 d . . . H15A H 0.6293 0.7673 -0.1114 0.133 Uiso 1 1 calc R . . H15B H 0.6255 0.7803 0.0148 0.133 Uiso 1 1 calc R . . C16 C 0.5128(4) 0.1511(11) -0.1673(6) 0.192(4) Uani 1 1 d . . . H16A H 0.4670 0.1180 -0.1371 0.288 Uiso 1 1 calc R . . H16B H 0.5165 0.0914 -0.2273 0.288 Uiso 1 1 calc R . . H16C H 0.4962 0.2406 -0.1984 0.288 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 0.0561(4) 0.0343(3) 0.0255(3) -0.00096(19) 0.0216(2) 0.0011(2) Na1 0.0709(7) 0.0315(4) 0.0275(4) -0.0008(3) 0.0248(4) -0.0022(4) O1 0.0809(12) 0.0266(7) 0.0336(8) 0.0055(6) 0.0336(8) 0.0039(7) O2 0.0714(12) 0.0358(8) 0.0341(8) 0.0079(6) 0.0259(8) 0.0060(7) N100 0.0526(12) 0.0395(9) 0.0368(10) 0.0010(8) 0.0258(9) 0.0046(8) O100 0.0745(13) 0.0590(11) 0.0349(9) -0.0096(8) 0.0342(9) -0.0041(9) N2 0.0628(13) 0.0405(10) 0.0440(11) -0.0143(8) 0.0339(10) -0.0104(9) N3 0.0547(11) 0.0315(8) 0.0315(9) -0.0071(7) 0.0237(8) -0.0012(8) C2 0.0517(12) 0.0282(9) 0.0243(9) -0.0013(7) 0.0177(9) 0.0045(8) C3 0.0526(14) 0.0411(11) 0.0394(12) 0.0018(9) 0.0214(11) -0.0009(10) C4 0.0563(15) 0.0475(13) 0.0489(14) 0.0063(11) 0.0272(12) 0.0005(11) C5 0.0650(18) 0.0663(17) 0.0474(15) -0.0039(13) 0.0306(14) -0.0091(14) C6 0.0644(18) 0.0636(17) 0.0550(17) 0.0103(14) 0.0212(14) 0.0126(14) C7 0.0584(18) 0.108(3) 0.0401(15) 0.0149(16) 0.0179(13) -0.0014(17) C8 0.099(3) 0.088(3) 0.121(4) 0.000(3) 0.069(3) -0.023(2) C9 0.068(2) 0.144(4) 0.0468(18) 0.022(2) 0.0101(16) -0.006(2) C10 0.062(2) 0.134(4) 0.060(2) -0.003(2) 0.0339(17) -0.008(2) C11 0.0598(18) 0.0649(18) 0.075(2) -0.0055(15) 0.0334(16) 0.0060(14) C12 0.056(2) 0.161(5) 0.078(3) 0.012(3) 0.008(2) -0.002(2) C13 0.059(2) 0.212(6) 0.091(3) -0.008(4) 0.034(2) -0.014(3) C14 0.081(3) 0.167(6) 0.171(6) -0.026(5) 0.036(4) -0.052(4) C15 0.059(2) 0.139(5) 0.136(4) 0.005(4) 0.035(3) 0.014(3) C16 0.065(3) 0.373(13) 0.107(5) 0.012(6) -0.009(3) -0.008(5) _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 O100 1.4467(16) . ? S1 O2 1.4553(17) . ? S1 N3 1.5748(19) . ? S1 C3 1.770(3) . ? S1 Na1 3.1575(11) . ? Na1 O1 2.3260(17) . ? Na1 O1 2.3277(17) 3_766 ? Na1 O2 2.4231(19) 2_755 ? Na1 N3 2.5530(19) . ? Na1 O100 2.597(2) . ? Na1 N100 2.610(2) 4_566 ? Na1 C2 3.125(2) 4_566 ? Na1 Na1 3.7571(16) 3_766 ? O1 C2 1.237(2) 2_755 ? O1 Na1 2.3277(17) 3_766 ? O2 Na1 2.4231(19) 2_745 ? N100 N2 1.409(2) . ? N100 C6 1.457(4) 3_765 ? N100 C4 1.467(3) 3_765 ? N100 Na1 2.610(2) 4_565 ? N2 C2 1.350(3) . ? N3 C2 1.373(2) . ? C2 O1 1.237(2) 2_745 ? C2 Na1 3.125(2) 4_565 ? C3 C10 1.371(4) . ? C3 C7 1.371(4) . ? C4 N100 1.467(3) 3_765 ? C4 C5 1.544(4) . ? C5 C8 1.514(5) . ? C5 C11 1.557(5) . ? C6 N100 1.457(4) 3_765 ? C6 C11 1.532(4) . ? C7 C9 1.363(5) . ? C8 C14 1.544(8) . ? C9 C12 1.350(6) . ? C10 C13 1.377(6) . ? C11 C15 1.497(5) . ? C12 C13 1.384(7) . ? C12 C16 1.530(6) . ? C14 C15 1.499(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 O100 S1 O2 114.40(10) . . ? O100 S1 N3 106.05(10) . . ? O2 S1 N3 114.72(10) . . ? O100 S1 C3 106.30(12) . . ? O2 S1 C3 104.74(11) . . ? N3 S1 C3 110.35(11) . . ? O100 S1 Na1 54.41(8) . . ? O2 S1 Na1 122.15(8) . . ? N3 S1 Na1 53.38(7) . . ? C3 S1 Na1 133.07(8) . . ? O1 Na1 O1 72.33(6) . 3_766 ? O1 Na1 O2 73.46(6) . 2_755 ? O1 Na1 O2 140.72(7) 3_766 2_755 ? O1 Na1 N3 140.51(7) . . ? O1 Na1 N3 138.71(7) 3_766 . ? O2 Na1 N3 80.57(6) 2_755 . ? O1 Na1 O100 132.17(7) . . ? O1 Na1 O100 83.75(6) 3_766 . ? O2 Na1 O100 134.52(6) 2_755 . ? N3 Na1 O100 55.92(6) . . ? O1 Na1 N100 114.98(7) . 4_566 ? O1 Na1 N100 65.12(6) 3_766 4_566 ? O2 Na1 N100 114.57(7) 2_755 4_566 ? N3 Na1 N100 102.64(7) . 4_566 ? O100 Na1 N100 89.56(7) . 4_566 ? O1 Na1 C2 91.17(6) . 4_566 ? O1 Na1 C2 20.21(5) 3_766 4_566 ? O2 Na1 C2 149.30(7) 2_755 4_566 ? N3 Na1 C2 124.40(6) . 4_566 ? O100 Na1 C2 75.32(6) . 4_566 ? N100 Na1 C2 47.93(6) 4_566 4_566 ? O1 Na1 S1 148.95(6) . . ? O1 Na1 S1 109.10(5) 3_766 . ? O2 Na1 S1 110.15(5) 2_755 . ? N3 Na1 S1 29.68(4) . . ? O100 Na1 S1 26.93(4) . . ? N100 Na1 S1 92.08(5) 4_566 . ? C2 Na1 S1 96.79(5) 4_566 . ? O1 Na1 Na1 36.18(4) . 3_766 ? O1 Na1 Na1 36.15(4) 3_766 3_766 ? O2 Na1 Na1 107.66(5) 2_755 3_766 ? N3 Na1 Na1 160.60(7) . 3_766 ? O100 Na1 Na1 110.37(5) . 3_766 ? N100 Na1 Na1 90.05(5) 4_566 3_766 ? C2 Na1 Na1 55.34(4) 4_566 3_766 ? S1 Na1 Na1 137.15(4) . 3_766 ? C2 O1 Na1 128.53(14) 2_755 . ? C2 O1 Na1 119.25(13) 2_755 3_766 ? Na1 O1 Na1 107.67(6) . 3_766 ? S1 O2 Na1 129.67(9) . 2_745 ? N2 N100 C6 113.9(2) . 3_765 ? N2 N100 C4 111.67(19) . 3_765 ? C6 N100 C4 104.9(2) 3_765 3_765 ? N2 N100 Na1 104.66(14) . 4_565 ? C6 N100 Na1 108.17(17) 3_765 4_565 ? C4 N100 Na1 113.74(16) 3_765 4_565 ? S1 O100 Na1 98.66(9) . . ? C2 N2 N100 118.90(18) . . ? C2 N3 S1 119.30(15) . . ? C2 N3 Na1 135.14(15) . . ? S1 N3 Na1 96.94(8) . . ? O1 C2 N2 120.68(19) 2_745 . ? O1 C2 N3 126.7(2) 2_745 . ? N2 C2 N3 112.59(18) . . ? O1 C2 Na1 40.54(10) 2_745 4_565 ? N2 C2 Na1 83.70(12) . 4_565 ? N3 C2 Na1 156.01(16) . 4_565 ? C10 C3 C7 118.8(3) . . ? C10 C3 S1 118.7(2) . . ? C7 C3 S1 122.4(2) . . ? N100 C4 C5 101.4(2) 3_765 . ? C8 C5 C4 115.2(3) . . ? C8 C5 C11 105.9(3) . . ? C4 C5 C11 104.7(2) . . ? N100 C6 C11 102.8(2) 3_765 . ? C9 C7 C3 120.4(3) . . ? C5 C8 C14 103.1(4) . . ? C12 C9 C7 122.2(4) . . ? C3 C10 C13 119.8(3) . . ? C15 C11 C6 114.9(4) . . ? C15 C11 C5 106.8(3) . . ? C6 C11 C5 104.0(2) . . ? C9 C12 C13 117.5(4) . . ? C9 C12 C16 120.5(5) . . ? C13 C12 C16 121.9(5) . . ? C10 C13 C12 121.2(4) . . ? C15 C14 C8 104.3(5) . . ? C11 C15 C14 104.6(4) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.567 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 928877'