# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text6 _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'gerard Coquerel' _publ_contact_author_address ;Laboratoire SMS EA 3233 Universit\'e de Rouen B\^at IRCOF rue Tesniere 76821 Mont Saint Aignan Cedex ; _publ_contact_author_email gerard.coquerel@univ-rouen.fr loop_ _publ_author_name _publ_author_address 'D.Martins ' ;Laboratoire SMS EA 3233 Universit\'e de Rouen B\^at IRCOF rue Tesniere 76821 Mont Saint Aignan Cedex ; M.Sanselme ;Laboratoire SMS EA 3233 Universit\'e de Rouen B\^at IRCOF rue Tesniere 76821 Mont Saint Aignan Cedex ; O.Houssin ;Laboratoire SMS EA 3233 Universit\'e de Rouen B\^at IRCOF rue Tesniere 76821 Mont Saint Aignan Cedex ; P.Delphine ;IPSEN 5 avenue du Canada F-91966 LES ULIS ; C.Diolez ;IPSEN 5 avenue du Canada F-91966 LES ULIS ; G.Coquerel ;Laboratoire SMS EA 3233 Universit\'e de Rouen B\^at IRCOF rue Tesniere 76821 Mont Saint Aignan Cedex ; _publ_requested_category FO #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-10-18 at 15:57:15 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : bn83495t struct data_bn83495t _database_code_depnum_ccdc_archive 'CCDC 849363' #TrackingRef '- BN_Form_I_CCDC849363.cif' _audit_creation_date 2011-10-18T15:57:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H15 N1 O5 S1' _chemical_formula_sum 'C14 H15 N O5 S' _chemical_formula_weight 309.33 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.995(5) _cell_length_b 11.236(5) _cell_length_c 10.403(5) _cell_angle_alpha 90 _cell_angle_beta 99.090(7) _cell_angle_gamma 90 _cell_volume 1384.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_unetI/netI 0.0254 _diffrn_reflns_number 9781 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.47 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2818 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0562P)^2^+0.1899P] 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_number_reflns 2818 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.294 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 -0.12321(4) 0.22476(4) 0.50298(4) 0.04146(17) Uani 1 1 d . . . N1 N -0.20580(14) 0.25309(19) 0.37424(17) 0.0473(4) Uani 1 1 d . . . H1N H -0.178(2) 0.230(2) 0.306(2) 0.070(8) Uiso 1 1 d . . . H2N H -0.225(2) 0.326(2) 0.376(2) 0.071(8) Uiso 1 1 d . . . O1 O 0.20113(10) 0.08713(11) 0.23123(13) 0.0449(3) Uani 1 1 d . . . O2 O -0.01194(11) 0.30363(13) 0.50358(13) 0.0533(4) Uani 1 1 d . . . O3 O 0.30021(12) -0.02065(12) 0.11490(14) 0.0538(4) Uani 1 1 d . . . O4 O -0.09332(13) 0.10373(13) 0.50211(17) 0.0696(5) Uani 1 1 d . . . O5 O -0.16801(12) 0.27483(14) 0.60876(13) 0.0587(4) Uani 1 1 d . . . C1 C 0.05609(15) 0.29592(17) 0.40520(18) 0.0415(4) Uani 1 1 d . . . C2 C 0.09254(15) 0.18966(16) 0.36181(18) 0.0415(4) Uani 1 1 d . . . H2 H 0.068 0.1172 0.3904 0.05 Uiso 1 1 calc R . . C3 C 0.16756(14) 0.19510(15) 0.27341(18) 0.0370(4) Uani 1 1 d . . . C4 C 0.20975(14) 0.30083(16) 0.23089(18) 0.0380(4) Uani 1 1 d . . . C5 C 0.16813(16) 0.40585(17) 0.2778(2) 0.0479(5) Uani 1 1 d . . . H12 H 0.193 0.4788 0.2509 0.057 Uiso 1 1 calc R . . C6 C 0.09148(16) 0.40358(18) 0.3626(2) 0.0500(5) Uani 1 1 d . . . H6 H 0.0635 0.4743 0.3913 0.06 Uiso 1 1 calc R . . C7 C 0.27897(14) 0.07918(17) 0.14846(18) 0.0400(4) Uani 1 1 d . . . C8 C 0.33024(15) 0.18692(16) 0.10978(18) 0.0400(4) Uani 1 1 d . . . C9 C 0.29619(14) 0.29454(16) 0.14723(18) 0.0390(4) Uani 1 1 d . . . C10 C 0.35166(16) 0.40556(17) 0.1065(2) 0.0487(5) Uani 1 1 d . . . H10A H 0.3119 0.4746 0.1322 0.058 Uiso 1 1 calc R . . H10B H 0.3455 0.4065 0.0124 0.058 Uiso 1 1 calc R . . C11 C 0.47687(16) 0.41443(18) 0.1670(2) 0.0487(5) Uani 1 1 d . . . H11A H 0.4995 0.4973 0.1669 0.058 Uiso 1 1 calc R . . H11B H 0.4848 0.3889 0.2571 0.058 Uiso 1 1 calc R . . C12 C 0.55714(17) 0.3420(2) 0.0994(2) 0.0538(5) Uani 1 1 d . . . H12A H 0.551 0.3696 0.0102 0.065 Uiso 1 1 calc R . . H12B H 0.6336 0.3579 0.1419 0.065 Uiso 1 1 calc R . . C13 C 0.53889(17) 0.20944(19) 0.0973(2) 0.0551(6) Uani 1 1 d . . . H13A H 0.5492 0.1806 0.1863 0.066 Uiso 1 1 calc R . . H13B H 0.596 0.1723 0.0544 0.066 Uiso 1 1 calc R . . C14 C 0.42300(17) 0.17080(19) 0.0287(2) 0.0519(5) Uani 1 1 d . . . H14A H 0.4042 0.2163 -0.051 0.062 Uiso 1 1 calc R . . H14B H 0.4264 0.0875 0.005 0.062 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 0.0391(3) 0.0520(3) 0.0357(3) 0.0075(2) 0.01355(19) 0.0066(2) N1 0.0474(10) 0.0592(12) 0.0359(9) -0.0023(8) 0.0081(7) 0.0080(8) O1 0.0431(7) 0.0380(7) 0.0572(8) -0.0037(6) 0.0196(6) -0.0025(5) O2 0.0439(8) 0.0729(10) 0.0460(8) -0.0155(7) 0.0162(6) -0.0064(6) O3 0.0534(8) 0.0429(8) 0.0684(10) -0.0103(7) 0.0195(7) 0.0013(6) O4 0.0694(10) 0.0517(10) 0.0950(13) 0.0264(8) 0.0355(9) 0.0168(8) O5 0.0557(9) 0.0910(12) 0.0333(7) 0.0019(7) 0.0193(6) 0.0071(8) C1 0.0300(9) 0.0565(12) 0.0385(10) -0.0050(8) 0.0064(7) -0.0009(8) C2 0.0348(9) 0.0446(11) 0.0463(11) -0.0009(8) 0.0100(8) -0.0044(8) C3 0.0295(9) 0.0385(10) 0.0424(10) -0.0023(8) 0.0046(7) 0.0005(7) C4 0.0302(9) 0.0399(10) 0.0435(11) 0.0017(8) 0.0048(8) 0.0013(7) C5 0.0457(11) 0.0386(10) 0.0619(13) 0.0022(9) 0.0160(9) 0.0026(8) C6 0.0455(11) 0.0442(11) 0.0626(13) -0.0055(10) 0.0151(9) 0.0063(9) C7 0.0322(9) 0.0453(11) 0.0423(10) -0.0043(8) 0.0047(7) -0.0001(8) C8 0.0316(9) 0.0479(11) 0.0411(10) -0.0031(8) 0.0076(8) -0.0022(7) C9 0.0309(9) 0.0444(10) 0.0411(10) 0.0046(8) 0.0037(7) -0.0001(7) C10 0.0436(10) 0.0464(11) 0.0589(13) 0.0097(10) 0.0161(9) 0.0002(8) C11 0.0473(11) 0.0493(12) 0.0511(12) 0.0051(9) 0.0129(9) -0.0104(9) C12 0.0393(10) 0.0663(14) 0.0571(13) 0.0092(11) 0.0115(9) -0.0084(9) C13 0.0402(11) 0.0626(14) 0.0664(14) 0.0034(11) 0.0207(10) 0.0041(9) C14 0.0501(12) 0.0579(13) 0.0522(12) -0.0100(10) 0.0215(10) -0.0033(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 1.4067(16) . ? S1 O5 1.4153(15) . ? S1 N1 1.5676(18) . ? S1 O2 1.6013(15) . ? N1 H1N 0.88(3) . ? N1 H2N 0.85(2) . ? O1 C7 1.369(2) . ? O1 C3 1.372(2) . ? O2 C1 1.409(2) . ? O3 C7 1.214(2) . ? C1 C2 1.372(3) . ? C1 C6 1.378(3) . ? C2 C3 1.386(3) . ? C2 H2 0.93 . ? C3 C4 1.391(2) . ? C4 C5 1.399(3) . ? C4 C9 1.457(3) . ? C5 C6 1.372(3) . ? C5 H12 0.93 . ? C6 H6 0.93 . ? C7 C8 1.444(3) . ? C8 C9 1.353(3) . ? C8 C14 1.509(3) . ? C9 C10 1.506(2) . ? C10 C11 1.537(3) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.516(3) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.505(3) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.522(3) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? 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 O4 S1 O5 121.18(10) . . ? O4 S1 N1 108.55(11) . . ? O5 S1 N1 108.49(10) . . ? O4 S1 O2 108.78(9) . . ? O5 S1 O2 101.28(9) . . ? N1 S1 O2 107.75(9) . . ? S1 N1 H1N 111.1(16) . . ? S1 N1 H2N 108.1(17) . . ? H1N N1 H2N 116(2) . . ? C7 O1 C3 121.50(14) . . ? C1 O2 S1 122.77(12) . . ? C2 C1 C6 121.86(18) . . ? C2 C1 O2 122.94(17) . . ? C6 C1 O2 115.00(17) . . ? C1 C2 C3 117.00(17) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? O1 C3 C2 115.30(16) . . ? O1 C3 C4 120.91(16) . . ? C2 C3 C4 123.76(17) . . ? C3 C4 C5 116.22(17) . . ? C3 C4 C9 118.53(16) . . ? C5 C4 C9 125.19(17) . . ? C6 C5 C4 121.42(18) . . ? C6 C5 H12 119.3 . . ? C4 C5 H12 119.3 . . ? C5 C6 C1 119.66(18) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? O3 C7 O1 115.86(16) . . ? O3 C7 C8 125.22(17) . . ? O1 C7 C8 118.91(16) . . ? C9 C8 C7 120.52(17) . . ? C9 C8 C14 123.42(17) . . ? C7 C8 C14 116.05(17) . . ? C8 C9 C4 119.41(16) . . ? C8 C9 C10 119.50(17) . . ? C4 C9 C10 121.05(16) . . ? C9 C10 C11 112.65(16) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 115.23(17) . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 115.89(17) . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 114.15(18) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C8 C14 C13 113.77(17) . . ? C8 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C8 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 O4 S1 O2 C1 58.51(17) . . . . ? O5 S1 O2 C1 -172.78(15) . . . . ? N1 S1 O2 C1 -58.98(17) . . . . ? S1 O2 C1 C2 -48.4(2) . . . . ? S1 O2 C1 C6 136.71(15) . . . . ? C6 C1 C2 C3 0.4(3) . . . . ? O2 C1 C2 C3 -174.12(16) . . . . ? C7 O1 C3 C2 -176.97(16) . . . . ? C7 O1 C3 C4 1.5(2) . . . . ? C1 C2 C3 O1 -179.34(15) . . . . ? C1 C2 C3 C4 2.2(3) . . . . ? O1 C3 C4 C5 178.71(15) . . . . ? C2 C3 C4 C5 -2.9(3) . . . . ? O1 C3 C4 C9 -4.0(3) . . . . ? C2 C3 C4 C9 174.31(17) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C9 C4 C5 C6 -175.99(18) . . . . ? C4 C5 C6 C1 1.4(3) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? O2 C1 C6 C5 172.76(17) . . . . ? C3 O1 C7 O3 -178.18(15) . . . . ? C3 O1 C7 C8 2.8(2) . . . . ? O3 C7 C8 C9 176.48(18) . . . . ? O1 C7 C8 C9 -4.6(3) . . . . ? O3 C7 C8 C14 -4.4(3) . . . . ? O1 C7 C8 C14 174.49(16) . . . . ? C7 C8 C9 C4 2.1(3) . . . . ? C14 C8 C9 C4 -176.96(17) . . . . ? C7 C8 C9 C10 179.51(16) . . . . ? C14 C8 C9 C10 0.5(3) . . . . ? C3 C4 C9 C8 2.2(3) . . . . ? C5 C4 C9 C8 179.16(18) . . . . ? C3 C4 C9 C10 -175.20(16) . . . . ? C5 C4 C9 C10 1.8(3) . . . . ? C8 C9 C10 C11 -65.5(2) . . . . ? C4 C9 C10 C11 111.91(19) . . . . ? C9 C10 C11 C12 80.5(2) . . . . ? C10 C11 C12 C13 -61.6(2) . . . . ? C11 C12 C13 C14 60.2(3) . . . . ? C9 C8 C14 C13 65.5(3) . . . . ? C7 C8 C14 C13 -113.6(2) . . . . ? C12 C13 C14 C8 -78.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O5 0.88(3) 2.07(3) 2.886(3) 154(2) 4_565 N1 H2N O3 0.85(2) 1.96(3) 2.793(3) 167(2) 2 #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-10-18 at 16:08:38 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : bn83495_form_3 struct data_bn83495_form_3 _database_code_depnum_ccdc_archive 'CCDC 849364' #TrackingRef '- BN_Form_III_CCDC849364_.cif' _audit_creation_date 2011-10-18T16:08:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H15 N1 O5 S1' _chemical_formula_sum 'C14 H15 N O5 S' _chemical_formula_weight 309.33 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.3275(12) _cell_length_b 20.489(2) _cell_length_c 7.8699(8) _cell_angle_alpha 90 _cell_angle_beta 131.5490(10) _cell_angle_gamma 90 _cell_volume 1366.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_unetI/netI 0.0276 _diffrn_reflns_number 3947 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2015 _reflns_number_gt 1931 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0517P)^2^+0.3780P] 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_number_reflns 2015 _refine_ls_number_parameters 198 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(8) _refine_diff_density_max 0.256 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 1.45344(8) -0.18908(2) 1.15708(11) 0.04051(17) Uani 1 1 d . . . O1 O 0.9079(2) -0.05688(8) 0.5756(3) 0.0392(4) Uani 1 1 d . . . O2 O 1.3824(2) -0.14496(9) 1.2407(3) 0.0481(5) Uani 1 1 d . . . O3 O 0.6862(3) -0.02503(10) 0.2510(3) 0.0570(6) Uani 1 1 d . . . O4 O 1.3672(3) -0.17541(11) 0.9246(3) 0.0622(6) Uani 1 1 d . . . O5 O 1.4551(3) -0.25223(10) 1.2277(5) 0.0732(7) Uani 1 1 d . . . N1 N 1.6289(3) -0.16606(18) 1.2982(5) 0.0546(7) Uani 1 1 d . . . HN1 H 1.697(6) -0.1842(18) 1.435(8) 0.078(13) Uiso 1 1 d . . . HN2 H 1.643(5) -0.1342(19) 1.287(6) 0.056(12) Uiso 1 1 d . . . C1 C 1.2910(3) -0.09039(12) 1.1114(4) 0.0357(5) Uani 1 1 d . . . C2 C 1.1424(3) -0.09952(11) 0.9041(4) 0.0366(5) Uani 1 1 d . . . H2 H 1.1025 -0.1412 0.8483 0.044 Uiso 1 1 calc R . . C3 C 1.0541(3) -0.04493(11) 0.7814(4) 0.0308(5) Uani 1 1 d . . . C4 C 1.1093(3) 0.01872(11) 0.8587(4) 0.0322(5) Uani 1 1 d . . . C5 C 1.2593(3) 0.02488(12) 1.0745(4) 0.0402(6) Uani 1 1 d . . . H5 H 1.2982 0.0664 1.1349 0.048 Uiso 1 1 calc R . . C6 C 1.3504(3) -0.02841(13) 1.1996(4) 0.0418(6) Uani 1 1 d . . . H6 H 1.4506 -0.0231 1.3414 0.05 Uiso 1 1 calc R . . C7 C 0.8111(3) -0.00780(12) 0.4284(4) 0.0392(6) Uani 1 1 d . . . C8 C 0.8699(3) 0.05892(11) 0.4976(4) 0.0372(5) Uani 1 1 d . . . C9 C 1.0098(3) 0.07180(11) 0.7049(4) 0.0344(5) Uani 1 1 d . . . C10 C 1.0637(3) 0.14210(11) 0.7790(5) 0.0434(6) Uani 1 1 d . . . H10A H 1.0682 0.1631 0.6729 0.052 Uiso 1 1 calc R . . H10B H 1.1693 0.1424 0.9273 0.052 Uiso 1 1 calc R . . C11 C 0.9541(4) 0.18092(12) 0.7904(5) 0.0456(6) Uani 1 1 d . . . H11A H 0.9218 0.1531 0.853 0.055 Uiso 1 1 calc R . . H11B H 1.0129 0.2172 0.8944 0.055 Uiso 1 1 calc R . . C12 C 0.8072(4) 0.20763(14) 0.5641(5) 0.0556(8) Uani 1 1 d . . . H12A H 0.7523 0.2355 0.5918 0.067 Uiso 1 1 calc R . . H12B H 0.8398 0.2347 0.5004 0.067 Uiso 1 1 calc R . . C13 C 0.6921(4) 0.15681(15) 0.3890(5) 0.0548(8) Uani 1 1 d . . . H13A H 0.6016 0.1789 0.2538 0.066 Uiso 1 1 calc R . . H13B H 0.655 0.1309 0.4487 0.066 Uiso 1 1 calc R . . C14 C 0.7630(4) 0.11106(13) 0.3226(5) 0.0475(7) Uani 1 1 d . . . H14A H 0.6778 0.0901 0.1798 0.057 Uiso 1 1 calc R . . H14B H 0.8227 0.1369 0.2988 0.057 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 0.0383(3) 0.0293(3) 0.0448(3) -0.0033(3) 0.0237(3) 0.0041(3) O1 0.0337(10) 0.0277(8) 0.0421(10) -0.0021(7) 0.0192(8) -0.0020(7) O2 0.0526(12) 0.0480(10) 0.0433(10) 0.0115(8) 0.0317(10) 0.0198(9) O3 0.0397(12) 0.0482(11) 0.0429(11) -0.0095(8) 0.0104(10) -0.0041(9) O4 0.0559(14) 0.0715(13) 0.0406(11) -0.0108(9) 0.0241(11) 0.0178(11) O5 0.0837(17) 0.0362(9) 0.109(2) 0.0082(11) 0.0678(17) 0.0071(11) N1 0.0431(16) 0.0580(17) 0.0537(17) -0.0042(14) 0.0282(14) -0.0035(13) C1 0.0352(13) 0.0378(12) 0.0368(13) 0.0035(10) 0.0250(11) 0.0079(10) C2 0.0398(14) 0.0293(11) 0.0429(14) -0.0037(9) 0.0284(13) -0.0014(9) C3 0.0263(12) 0.0313(11) 0.0313(12) -0.0028(8) 0.0176(10) -0.0016(9) C4 0.0340(13) 0.0293(11) 0.0363(12) -0.0037(9) 0.0246(11) -0.0004(9) C5 0.0362(14) 0.0359(12) 0.0397(13) -0.0104(10) 0.0215(12) -0.0052(10) C6 0.0331(13) 0.0464(14) 0.0345(12) -0.0047(10) 0.0177(11) 0.0037(10) C7 0.0354(14) 0.0387(12) 0.0343(12) -0.0021(10) 0.0192(12) 0.0038(11) C8 0.0411(14) 0.0325(11) 0.0363(12) 0.0018(9) 0.0249(12) 0.0042(10) C9 0.0356(13) 0.0293(10) 0.0389(13) -0.0026(9) 0.0250(12) -0.0001(9) C10 0.0424(15) 0.0311(12) 0.0542(16) -0.0027(10) 0.0310(14) -0.0014(11) C11 0.0485(16) 0.0342(12) 0.0535(16) -0.0066(11) 0.0335(14) -0.0017(11) C12 0.059(2) 0.0427(14) 0.0606(19) 0.0046(13) 0.0379(17) 0.0169(13) C13 0.0478(17) 0.0515(16) 0.0479(17) 0.0069(12) 0.0244(15) 0.0164(13) C14 0.0522(17) 0.0434(13) 0.0347(13) 0.0039(10) 0.0236(13) 0.0067(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O5 1.403(2) . ? S1 O4 1.417(2) . ? S1 N1 1.574(3) . ? S1 O2 1.612(2) . ? O1 C3 1.367(3) . ? O1 C7 1.368(3) . ? O2 C1 1.400(3) . ? O3 C7 1.206(3) . ? N1 HN1 0.89(5) . ? N1 HN2 0.69(4) . ? C1 C2 1.374(3) . ? C1 C6 1.388(4) . ? C2 C3 1.379(3) . ? C2 H2 0.93 . ? C3 C4 1.399(3) . ? C4 C5 1.400(3) . ? C4 C9 1.452(3) . ? C5 C6 1.371(4) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.459(4) . ? C8 C9 1.347(4) . ? C8 C14 1.514(3) . ? C9 C10 1.522(3) . ? C10 C11 1.526(4) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.520(4) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.517(5) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.534(4) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? 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 O5 S1 O4 120.67(16) . . ? O5 S1 N1 108.55(19) . . ? O4 S1 N1 108.57(18) . . ? O5 S1 O2 103.57(13) . . ? O4 S1 O2 108.20(11) . . ? N1 S1 O2 106.39(14) . . ? C3 O1 C7 122.17(19) . . ? C1 O2 S1 118.68(15) . . ? S1 N1 HN1 114(3) . . ? S1 N1 HN2 119(4) . . ? HN1 N1 HN2 117(4) . . ? C2 C1 C6 121.6(2) . . ? C2 C1 O2 119.2(2) . . ? C6 C1 O2 119.2(2) . . ? C1 C2 C3 118.0(2) . . ? C1 C2 H2 121 . . ? C3 C2 H2 121 . . ? O1 C3 C2 115.5(2) . . ? O1 C3 C4 121.5(2) . . ? C2 C3 C4 123.0(2) . . ? C3 C4 C5 116.4(2) . . ? C3 C4 C9 117.4(2) . . ? C5 C4 C9 126.2(2) . . ? C6 C5 C4 122.0(2) . . ? C6 C5 H5 119 . . ? C4 C5 H5 119 . . ? C5 C6 C1 119.0(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O3 C7 O1 115.5(2) . . ? O3 C7 C8 126.9(2) . . ? O1 C7 C8 117.5(2) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 C14 123.5(2) . . ? C7 C8 C14 115.5(2) . . ? C8 C9 C4 120.2(2) . . ? C8 C9 C10 120.0(2) . . ? C4 C9 C10 119.8(2) . . ? C9 C10 C11 112.4(2) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 114.8(3) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 115.5(2) . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 113.6(3) . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C8 C14 C13 113.9(2) . . ? C8 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C8 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 O5 S1 O2 C1 -147.7(2) . . . . ? O4 S1 O2 C1 -18.5(3) . . . . ? N1 S1 O2 C1 98.0(2) . . . . ? S1 O2 C1 C2 71.4(3) . . . . ? S1 O2 C1 C6 -111.1(2) . . . . ? C6 C1 C2 C3 1.8(4) . . . . ? O2 C1 C2 C3 179.3(2) . . . . ? C7 O1 C3 C2 -175.5(2) . . . . ? C7 O1 C3 C4 3.9(3) . . . . ? C1 C2 C3 O1 179.4(2) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? O1 C3 C4 C5 178.4(2) . . . . ? C2 C3 C4 C5 -2.2(4) . . . . ? O1 C3 C4 C9 -4.4(3) . . . . ? C2 C3 C4 C9 175.0(2) . . . . ? C3 C4 C5 C6 2.8(4) . . . . ? C9 C4 C5 C6 -174.1(3) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? O2 C1 C6 C5 -178.6(2) . . . . ? C3 O1 C7 O3 178.9(2) . . . . ? C3 O1 C7 C8 0.4(3) . . . . ? O3 C7 C8 C9 177.5(3) . . . . ? O1 C7 C8 C9 -4.3(4) . . . . ? O3 C7 C8 C14 -2.1(4) . . . . ? O1 C7 C8 C14 176.1(2) . . . . ? C7 C8 C9 C4 3.7(4) . . . . ? C14 C8 C9 C4 -176.7(2) . . . . ? C7 C8 C9 C10 -176.0(2) . . . . ? C14 C8 C9 C10 3.6(4) . . . . ? C3 C4 C9 C8 0.5(4) . . . . ? C5 C4 C9 C8 177.4(3) . . . . ? C3 C4 C9 C10 -179.7(2) . . . . ? C5 C4 C9 C10 -2.8(4) . . . . ? C8 C9 C10 C11 62.8(3) . . . . ? C4 C9 C10 C11 -117.0(3) . . . . ? C9 C10 C11 C12 -82.0(3) . . . . ? C10 C11 C12 C13 64.7(4) . . . . ? C11 C12 C13 C14 -60.5(4) . . . . ? C9 C8 C14 C13 -67.3(4) . . . . ? C7 C8 C14 C13 112.3(3) . . . . ? C12 C13 C14 C8 76.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 HN1 O5 0.89(5) 2.57(5) 3.363(4) 149(4) 4_545 N1 HN2 O3 0.69(4) 2.35(4) 3.038(4) 178(4) 1_656 data_bn_dioxane _database_code_depnum_ccdc_archive 'CCDC 849365' #TrackingRef '- BN_1_4_dioxane_CCDC849365_modified.cif' _audit_creation_date 2011-12-20T14:54:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H19 N1 O6 S1' _chemical_formula_sum 'C16 H19 N O6 S' _chemical_formula_weight 353.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.016(4) _cell_length_b 9.765(5) _cell_length_c 10.068(5) _cell_angle_alpha 67.731(9) _cell_angle_beta 78.939(8) _cell_angle_gamma 86.504(9) _cell_volume 805.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_unetI/netI 0.0839 _diffrn_reflns_number 4291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.45 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.909 _diffrn_measured_fraction_theta_max 0.909 _reflns_number_total 3016 _reflns_number_gt 1726 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0648P)^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_number_reflns 3016 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.254 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S S 0.04754(9) 0.71830(10) 0.10765(9) 0.0410(3) Uani 1 1 d . . . N1 N 0.0763(4) 0.5616(4) 0.0990(3) 0.0474(8) Uani 1 1 d . . . H1N H 0.169(4) 0.524(3) 0.100(3) 0.047(10) Uiso 1 1 d . . . H2N H 0.006(4) 0.507(4) 0.138(4) 0.054(12) Uiso 1 1 d . . . O1 O -0.1281(2) 1.1547(2) 0.2861(2) 0.0432(6) Uani 1 1 d . . . O2 O 0.0133(2) 0.6737(2) 0.2827(2) 0.0473(6) Uani 1 1 d . . . O3 O -0.1860(3) 1.3790(3) 0.2773(3) 0.0542(7) Uani 1 1 d . . . O4 O -0.0870(2) 0.7799(3) 0.0566(2) 0.0571(7) Uani 1 1 d . . . O5 O 0.1836(3) 0.8014(3) 0.0527(3) 0.0636(7) Uani 1 1 d . . . C1 C -0.0523(3) 0.7714(4) 0.3486(3) 0.0368(8) Uani 1 1 d . . . C2 C -0.0582(3) 0.9222(4) 0.2787(3) 0.0386(8) Uani 1 1 d . . . H2 H -0.0183 0.9683 0.1799 0.046 Uiso 1 1 calc R . . C3 C -0.1256(3) 1.0032(3) 0.3607(3) 0.0341(8) Uani 1 1 d . . . C4 C -0.1856(3) 0.9411(3) 0.5087(3) 0.0339(8) Uani 1 1 d . . . C5 C -0.1743(3) 0.7875(4) 0.5739(3) 0.0388(8) Uani 1 1 d . . . H5 H -0.2123 0.7407 0.673 0.047 Uiso 1 1 calc R . . C6 C -0.1092(3) 0.7036(4) 0.4965(3) 0.0408(8) Uani 1 1 d . . . H6 H -0.103 0.6015 0.543 0.049 Uiso 1 1 calc R . . C7 C -0.1928(3) 1.2484(4) 0.3529(4) 0.0413(8) Uani 1 1 d . . . C8 C -0.2612(3) 1.1854(4) 0.5065(3) 0.0385(8) Uani 1 1 d . . . C9 C -0.2564(3) 1.0376(4) 0.5824(3) 0.0349(8) Uani 1 1 d . . . C10 C -0.3269(4) 0.9732(4) 0.7424(3) 0.0457(9) Uani 1 1 d . . . H10A H -0.2839 1.0226 0.7939 0.055 Uiso 1 1 calc R . . H10B H -0.3023 0.8691 0.7822 0.055 Uiso 1 1 calc R . . C11 C -0.4991(4) 0.9893(4) 0.7686(4) 0.0563(10) Uani 1 1 d . . . H11A H -0.5381 0.9711 0.6934 0.068 Uiso 1 1 calc R . . H11B H -0.5416 0.9141 0.8618 0.068 Uiso 1 1 calc R . . C12 C -0.5519(4) 1.1392(4) 0.7687(4) 0.0592(11) Uani 1 1 d . . . H12A H -0.5123 1.1569 0.8439 0.071 Uiso 1 1 calc R . . H12B H -0.6612 1.1361 0.7953 0.071 Uiso 1 1 calc R . . C13 C -0.5070(4) 1.2689(4) 0.6262(4) 0.0574(10) Uani 1 1 d . . . H13A H -0.55 1.3581 0.6377 0.069 Uiso 1 1 calc R . . H13B H -0.5506 1.2541 0.5516 0.069 Uiso 1 1 calc R . . C14 C -0.3361(4) 1.2922(4) 0.5734(4) 0.0502(9) Uani 1 1 d . . . H14A H -0.3171 1.3921 0.5018 0.06 Uiso 1 1 calc R . . H14B H -0.2896 1.2835 0.6554 0.06 Uiso 1 1 calc R . . O1B O 0.3697(2) 0.4239(3) 0.0922(2) 0.0522(7) Uani 1 1 d . . . C2B C 0.4194(4) 0.4156(4) -0.0477(4) 0.0508(10) Uani 1 1 d . . . H2B1 H 0.3331 0.4027 -0.0866 0.061 Uiso 1 1 calc R . . H2B2 H 0.4849 0.3312 -0.0391 0.061 Uiso 1 1 calc R . . C3B C 0.5035(4) 0.5549(4) -0.1488(4) 0.0589(11) Uani 1 1 d . . . H3B1 H 0.4365 0.6386 -0.1606 0.071 Uiso 1 1 calc R . . H3B2 H 0.5381 0.5493 -0.244 0.071 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 S 0.0439(5) 0.0436(6) 0.0324(5) -0.0125(4) -0.0014(4) -0.0044(4) N1 0.042(2) 0.048(2) 0.052(2) -0.0215(17) 0.0009(16) -0.0070(18) O1 0.0567(14) 0.0331(15) 0.0311(13) -0.0027(12) -0.0061(10) -0.0044(11) O2 0.0645(15) 0.0397(15) 0.0335(14) -0.0112(12) -0.0064(11) 0.0078(12) O3 0.0665(16) 0.0275(16) 0.0548(17) -0.0009(13) -0.0077(12) -0.0047(12) O4 0.0528(15) 0.0672(18) 0.0522(16) -0.0206(14) -0.0202(12) 0.0158(13) O5 0.0596(15) 0.0630(18) 0.0615(17) -0.0215(14) 0.0092(12) -0.0277(13) C1 0.0339(17) 0.045(2) 0.032(2) -0.0152(18) -0.0054(14) -0.0009(15) C2 0.0427(19) 0.043(2) 0.0266(18) -0.0080(17) -0.0056(14) -0.0064(16) C3 0.0359(17) 0.030(2) 0.0321(19) -0.0046(17) -0.0094(14) -0.0056(14) C4 0.0320(16) 0.033(2) 0.0320(19) -0.0065(17) -0.0044(14) -0.0048(14) C5 0.0425(18) 0.038(2) 0.0267(18) -0.0040(17) -0.0003(14) -0.0019(15) C6 0.0429(18) 0.034(2) 0.036(2) -0.0030(17) -0.0044(15) -0.0028(15) C7 0.0433(19) 0.035(2) 0.044(2) -0.009(2) -0.0138(16) -0.0056(16) C8 0.0362(18) 0.039(2) 0.039(2) -0.0126(18) -0.0065(15) -0.0056(15) C9 0.0357(17) 0.034(2) 0.0323(19) -0.0086(17) -0.0070(14) -0.0062(14) C10 0.054(2) 0.041(2) 0.036(2) -0.0127(18) -0.0008(16) 0.0032(17) C11 0.051(2) 0.056(3) 0.057(2) -0.023(2) 0.0095(18) -0.0106(19) C12 0.039(2) 0.069(3) 0.071(3) -0.033(3) -0.0025(18) 0.0069(19) C13 0.053(2) 0.056(3) 0.072(3) -0.033(2) -0.021(2) 0.0183(19) C14 0.062(2) 0.037(2) 0.053(2) -0.0176(19) -0.0114(18) 0.0000(17) O1B 0.0468(14) 0.0563(17) 0.0447(15) -0.0117(13) 0.0005(11) -0.0110(12) C2B 0.058(2) 0.048(2) 0.049(2) -0.019(2) -0.0111(18) -0.0091(18) C3B 0.066(2) 0.066(3) 0.039(2) -0.011(2) -0.0074(18) -0.015(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O5 1.411(2) . ? S O4 1.419(2) . ? S N1 1.569(3) . ? S O2 1.618(2) . ? N1 H1N 0.89(3) . ? N1 H2N 0.79(3) . ? O1 C7 1.371(4) . ? O1 C3 1.383(4) . ? O2 C1 1.400(3) . ? O3 C7 1.211(4) . ? C1 C2 1.374(4) . ? C1 C6 1.385(4) . ? C2 C3 1.386(4) . ? C2 H2 0.93 . ? C3 C4 1.388(4) . ? C4 C5 1.398(4) . ? C4 C9 1.456(4) . ? C5 C6 1.368(4) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.452(4) . ? C8 C9 1.356(4) . ? C8 C14 1.506(4) . ? C9 C10 1.510(4) . ? C10 C11 1.533(4) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.512(5) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.513(5) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.532(4) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? O1B C2B 1.426(4) . ? O1B C3B 1.429(4) 2_665 ? C2B C3B 1.497(4) . ? C2B H2B1 0.97 . ? C2B H2B2 0.97 . ? C3B O1B 1.429(4) 2_665 ? C3B H3B1 0.97 . ? C3B H3B2 0.97 . ? 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 O5 S O4 120.23(17) . . ? O5 S N1 109.27(18) . . ? O4 S N1 110.90(17) . . ? O5 S O2 107.16(13) . . ? O4 S O2 106.86(13) . . ? N1 S O2 100.47(15) . . ? S N1 H1N 119(2) . . ? S N1 H2N 113(2) . . ? H1N N1 H2N 119(4) . . ? C7 O1 C3 122.0(2) . . ? C1 O2 S 122.7(2) . . ? C2 C1 C6 120.9(3) . . ? C2 C1 O2 124.9(3) . . ? C6 C1 O2 114.1(3) . . ? C1 C2 C3 117.6(3) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? O1 C3 C2 115.7(3) . . ? O1 C3 C4 120.4(3) . . ? C2 C3 C4 123.9(3) . . ? C3 C4 C5 115.7(3) . . ? C3 C4 C9 118.8(3) . . ? C5 C4 C9 125.5(3) . . ? C6 C5 C4 122.1(3) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O3 C7 O1 116.1(3) . . ? O3 C7 C8 125.3(3) . . ? O1 C7 C8 118.5(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 C14 123.1(3) . . ? C7 C8 C14 116.5(3) . . ? C8 C9 C4 119.8(3) . . ? C8 C9 C10 120.0(3) . . ? C4 C9 C10 120.2(3) . . ? C9 C10 C11 112.5(3) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.2(3) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 115.8(3) . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 114.3(3) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C8 C14 C13 114.5(3) . . ? C8 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C8 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C2B O1B C3B 110.0(2) . 2_665 ? O1B C2B C3B 109.4(3) . . ? O1B C2B H2B1 109.8 . . ? C3B C2B H2B1 109.8 . . ? O1B C2B H2B2 109.8 . . ? C3B C2B H2B2 109.8 . . ? H2B1 C2B H2B2 108.2 . . ? C2B C3B O1B 110.4(3) . 2_665 ? C2B C3B H3B1 109.6 . . ? O1B C3B H3B1 109.6 2_665 . ? C2B C3B H3B2 109.6 . . ? O1B C3B H3B2 109.6 2_665 . ? H3B1 C3B H3B2 108.1 . . ? 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 O5 S O2 C1 80.6(2) . . . . ? O4 S O2 C1 -49.5(2) . . . . ? N1 S O2 C1 -165.3(2) . . . . ? S O2 C1 C2 -18.3(4) . . . . ? S O2 C1 C6 163.8(2) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? O2 C1 C2 C3 -179.1(3) . . . . ? C7 O1 C3 C2 179.2(3) . . . . ? C7 O1 C3 C4 -2.0(4) . . . . ? C1 C2 C3 O1 179.6(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? O1 C3 C4 C5 -178.7(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? O1 C3 C4 C9 2.5(4) . . . . ? C2 C3 C4 C9 -178.8(3) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C9 C4 C5 C6 178.4(3) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C2 C1 C6 C5 1.1(5) . . . . ? O2 C1 C6 C5 179.1(3) . . . . ? C3 O1 C7 O3 178.8(3) . . . . ? C3 O1 C7 C8 -0.3(4) . . . . ? O3 C7 C8 C9 -177.0(3) . . . . ? O1 C7 C8 C9 2.0(4) . . . . ? O3 C7 C8 C14 3.3(5) . . . . ? O1 C7 C8 C14 -177.7(3) . . . . ? C7 C8 C9 C4 -1.5(4) . . . . ? C14 C8 C9 C4 178.2(3) . . . . ? C7 C8 C9 C10 179.6(3) . . . . ? C14 C8 C9 C10 -0.7(5) . . . . ? C3 C4 C9 C8 -0.7(4) . . . . ? C5 C4 C9 C8 -179.5(3) . . . . ? C3 C4 C9 C10 178.2(3) . . . . ? C5 C4 C9 C10 -0.5(5) . . . . ? C8 C9 C10 C11 66.0(4) . . . . ? C4 C9 C10 C11 -113.0(3) . . . . ? C9 C10 C11 C12 -82.0(4) . . . . ? C10 C11 C12 C13 63.6(4) . . . . ? C11 C12 C13 C14 -60.7(4) . . . . ? C9 C8 C14 C13 -63.9(4) . . . . ? C7 C8 C14 C13 115.9(3) . . . . ? C12 C13 C14 C8 76.6(4) . . . . ? C3B O1B C2B C3B -58.6(4) 2_665 . . . ? O1B C2B C3B O1B 58.9(4) . . . 2_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1B 0.89(3) 2.01(3) 2.894(4) 173(3) . N1 H2N O3 0.79(3) 2.13(4) 2.908(4) 168(3) 1_545 #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-01-22 at 09:07:31 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : bn38dmso struct data_bn38dmso _database_code_depnum_ccdc_archive 'CCDC 849366' #TrackingRef '- BN_DMSO_III_CCDC849366.cif' _audit_creation_date 2009-01-22T09:07:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H21 N1 O6 S2' _chemical_formula_sum 'C16 H21 N O6 S2' _chemical_formula_weight 387.46 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 13.8424(13) _cell_length_b 7.2425(7) _cell_length_c 18.7780(18) _cell_angle_alpha 90 _cell_angle_beta 104.950(2) _cell_angle_gamma 90 _cell_volume 1818.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_unetI/netI 0.0163 _diffrn_reflns_number 13920 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.42 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3710 _reflns_number_gt 3472 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0653P)^2^+0.7339P] 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_number_reflns 3710 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.386 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 S1S S 0.56790(4) -0.06783(9) 0.17938(3) 0.0598(2) Uani 1 1 d . . . O1S O 0.51404(14) -0.2300(3) 0.19954(10) 0.0758(5) Uani 1 1 d . . . C2S C 0.4755(3) 0.0819(4) 0.1282(2) 0.0821(9) Uani 1 1 d . . . H2S1 H 0.4344 0.0167 0.0869 0.123 Uiso 1 1 calc R . . H2S2 H 0.5069 0.1847 0.1109 0.123 Uiso 1 1 calc R . . H2S3 H 0.4348 0.126 0.159 0.123 Uiso 1 1 calc R . . C1S C 0.6168(2) -0.1393(5) 0.1053(2) 0.0880(9) Uani 1 1 d . . . H1S1 H 0.6696 -0.2271 0.1229 0.132 Uiso 1 1 calc R . . H1S2 H 0.6427 -0.0341 0.0852 0.132 Uiso 1 1 calc R . . H1S3 H 0.5647 -0.1955 0.0677 0.132 Uiso 1 1 calc R . . S1 S 0.68163(4) 0.41070(7) -0.03412(3) 0.04426(17) Uani 1 1 d . . . N1 N 0.61724(16) 0.4790(3) -0.11141(12) 0.0555(5) Uani 1 1 d . . . HN1 H 0.573(2) 0.395(4) -0.1360(15) 0.067(8) Uiso 1 1 d . . . HN2 H 0.649(2) 0.530(4) -0.1342(16) 0.064(9) Uiso 1 1 d . . . O1 O 1.07848(10) 0.29856(17) 0.10432(7) 0.0414(3) Uani 1 1 d . . . O2 O 0.75557(10) 0.2659(2) -0.05867(7) 0.0443(3) Uani 1 1 d . . . O3 O 1.23159(11) 0.3301(2) 0.17222(10) 0.0621(4) Uani 1 1 d . . . O4 O 0.74134(14) 0.5558(2) 0.00465(11) 0.0681(5) Uani 1 1 d . . . O5 O 0.62139(12) 0.3068(3) 0.00185(9) 0.0634(4) Uani 1 1 d . . . C1 C 0.83215(13) 0.1848(3) -0.00407(9) 0.0354(4) Uani 1 1 d . . . C2 C 0.91742(14) 0.2840(2) 0.02673(10) 0.0374(4) Uani 1 1 d . . . H2 H 0.923 0.4075 0.0148 0.045 Uiso 1 1 calc R . . C3 C 0.99469(13) 0.1942(2) 0.07605(9) 0.0332(4) Uani 1 1 d . . . C4 C 0.99015(13) 0.0094(2) 0.09544(9) 0.0317(4) Uani 1 1 d . . . C5 C 0.90093(14) -0.0851(2) 0.06239(10) 0.0362(4) Uani 1 1 d . . . H5 H 0.8946 -0.2085 0.0741 0.043 Uiso 1 1 calc R . . C6 C 0.82289(13) 0.0006(3) 0.01324(10) 0.0379(4) Uani 1 1 d . . . H6 H 0.7646 -0.0641 -0.0081 0.045 Uiso 1 1 calc R . . C7 C 1.16198(14) 0.2256(3) 0.15205(10) 0.0400(4) Uani 1 1 d . . . C8 C 1.15951(13) 0.0332(3) 0.17388(10) 0.0357(4) Uani 1 1 d . . . C9 C 1.07691(13) -0.0716(2) 0.14658(9) 0.0330(4) Uani 1 1 d . . . C10 C 1.07622(15) -0.2712(3) 0.16887(11) 0.0440(4) Uani 1 1 d . . . H10A H 1.1319 -0.3338 0.1568 0.053 Uiso 1 1 calc R . . H10B H 1.0151 -0.3281 0.1403 0.053 Uiso 1 1 calc R . . C11 C 1.08356(17) -0.2998(3) 0.25098(13) 0.0552(6) Uani 1 1 d . . . H11A H 1.0412 -0.2096 0.2663 0.066 Uiso 1 1 calc R . . H11B H 1.0576 -0.4213 0.2575 0.066 Uiso 1 1 calc R . . C12 C 1.18754(19) -0.2835(4) 0.30047(13) 0.0616(6) Uani 1 1 d . . . H12A H 1.2292 -0.3756 0.2855 0.074 Uiso 1 1 calc R . . H12B H 1.1851 -0.3134 0.3503 0.074 Uiso 1 1 calc R . . C13 C 1.23742(19) -0.0977(4) 0.30175(12) 0.0579(6) Uani 1 1 d . . . H13A H 1.3019 -0.1014 0.3376 0.07 Uiso 1 1 calc R . . H13B H 1.197 -0.0053 0.3179 0.07 Uiso 1 1 calc R . . C14 C 1.25303(15) -0.0382(3) 0.22713(11) 0.0466(5) Uani 1 1 d . . . H14A H 1.3037 0.0574 0.2353 0.056 Uiso 1 1 calc R . . H14B H 1.2779 -0.1429 0.2049 0.056 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 S1S 0.0518(3) 0.0645(4) 0.0567(4) 0.0067(3) 0.0024(3) -0.0102(3) O1S 0.0752(11) 0.0801(13) 0.0655(11) 0.0209(9) 0.0064(9) -0.0194(10) C2S 0.089(2) 0.0699(18) 0.089(2) 0.0148(15) 0.0256(17) 0.0201(15) C1S 0.0757(19) 0.088(2) 0.114(3) -0.0034(19) 0.0492(19) 0.0020(17) S1 0.0420(3) 0.0392(3) 0.0508(3) -0.0008(2) 0.0107(2) 0.00321(19) N1 0.0474(11) 0.0479(11) 0.0664(13) 0.0160(10) 0.0057(10) 0.0013(9) O1 0.0417(7) 0.0294(6) 0.0493(8) 0.0018(5) 0.0048(6) -0.0076(5) O2 0.0437(7) 0.0494(8) 0.0363(7) -0.0020(6) 0.0042(5) 0.0091(6) O3 0.0483(8) 0.0516(9) 0.0758(11) 0.0071(8) -0.0031(7) -0.0186(7) O4 0.0673(11) 0.0487(9) 0.0817(12) -0.0194(8) 0.0075(9) -0.0008(8) O5 0.0563(9) 0.0753(11) 0.0632(10) 0.0106(9) 0.0240(8) 0.0000(8) C1 0.0373(9) 0.0390(9) 0.0301(8) -0.0024(7) 0.0090(7) 0.0039(7) C2 0.0450(10) 0.0285(8) 0.0395(9) 0.0011(7) 0.0124(8) -0.0002(7) C3 0.0364(9) 0.0306(8) 0.0335(8) -0.0039(7) 0.0106(7) -0.0051(7) C4 0.0367(9) 0.0304(8) 0.0303(8) -0.0027(6) 0.0126(7) -0.0017(7) C5 0.0422(10) 0.0289(8) 0.0390(9) -0.0024(7) 0.0135(7) -0.0045(7) C6 0.0360(9) 0.0390(10) 0.0391(9) -0.0074(8) 0.0106(7) -0.0059(8) C7 0.0382(9) 0.0399(10) 0.0406(10) -0.0009(8) 0.0080(7) -0.0061(8) C8 0.0375(9) 0.0390(9) 0.0315(8) 0.0003(7) 0.0106(7) -0.0005(7) C9 0.0407(9) 0.0296(8) 0.0309(8) -0.0009(6) 0.0133(7) -0.0001(7) C10 0.0493(11) 0.0312(9) 0.0502(11) 0.0048(8) 0.0103(9) 0.0008(8) C11 0.0594(13) 0.0504(12) 0.0613(13) 0.0215(10) 0.0252(11) 0.0042(10) C12 0.0703(15) 0.0707(15) 0.0452(12) 0.0228(11) 0.0174(11) 0.0132(12) C13 0.0613(14) 0.0699(15) 0.0375(11) 0.0062(10) 0.0036(9) 0.0050(11) C14 0.0391(10) 0.0532(11) 0.0452(11) 0.0056(9) 0.0067(8) 0.0007(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1S O1S 1.4916(19) . ? S1S C2S 1.761(3) . ? S1S C1S 1.775(3) . ? C2S H2S1 0.96 . ? C2S H2S2 0.96 . ? C2S H2S3 0.96 . ? C1S H1S1 0.96 . ? C1S H1S2 0.96 . ? C1S H1S3 0.96 . ? S1 O4 1.4165(17) . ? S1 O5 1.4173(16) . ? S1 N1 1.574(2) . ? S1 O2 1.6136(14) . ? N1 HN1 0.90(3) . ? N1 HN2 0.78(3) . ? O1 C3 1.371(2) . ? O1 C7 1.372(2) . ? O2 C1 1.400(2) . ? O3 C7 1.207(2) . ? C1 C2 1.375(3) . ? C1 C6 1.387(3) . ? C2 C3 1.383(3) . ? C2 H2 0.93 . ? C3 C4 1.393(2) . ? C4 C5 1.408(2) . ? C4 C9 1.454(2) . ? C5 C6 1.375(3) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.456(3) . ? C8 C9 1.358(3) . ? C8 C14 1.509(3) . ? C9 C10 1.506(2) . ? C10 C11 1.533(3) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.503(3) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.510(4) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.534(3) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? 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 O1S S1S C2S 106.45(14) . . ? O1S S1S C1S 106.63(15) . . ? C2S S1S C1S 97.03(17) . . ? S1S C2S H2S1 109.5 . . ? S1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? S1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? S1S C1S H1S1 109.5 . . ? S1S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? S1S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? O4 S1 O5 119.08(12) . . ? O4 S1 N1 110.94(12) . . ? O5 S1 N1 110.09(11) . . ? O4 S1 O2 107.45(9) . . ? O5 S1 O2 106.59(10) . . ? N1 S1 O2 100.99(10) . . ? S1 N1 HN1 114.1(18) . . ? S1 N1 HN2 113(2) . . ? HN1 N1 HN2 116(3) . . ? C3 O1 C7 121.76(14) . . ? C1 O2 S1 118.67(11) . . ? C2 C1 C6 121.68(17) . . ? C2 C1 O2 119.64(16) . . ? C6 C1 O2 118.49(16) . . ? C1 C2 C3 117.86(16) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? O1 C3 C2 115.51(15) . . ? O1 C3 C4 121.28(16) . . ? C2 C3 C4 123.20(16) . . ? C3 C4 C5 116.45(16) . . ? C3 C4 C9 118.36(15) . . ? C5 C4 C9 125.19(16) . . ? C6 C5 C4 121.62(16) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 119.19(16) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O3 C7 O1 115.68(17) . . ? O3 C7 C8 125.94(18) . . ? O1 C7 C8 118.37(15) . . ? C9 C8 C7 120.50(16) . . ? C9 C8 C14 123.61(17) . . ? C7 C8 C14 115.88(16) . . ? C8 C9 C4 119.71(16) . . ? C8 C9 C10 119.79(17) . . ? C4 C9 C10 120.50(16) . . ? C9 C10 C11 113.95(17) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 114.57(18) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 116.15(19) . . ? C11 C12 H12A 108.2 . . ? C13 C12 H12A 108.2 . . ? C11 C12 H12B 108.2 . . ? C13 C12 H12B 108.2 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 114.0(2) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C8 C14 C13 113.76(17) . . ? C8 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C8 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 O4 S1 O2 C1 58.25(16) . . . . ? O5 S1 O2 C1 -70.45(15) . . . . ? N1 S1 O2 C1 174.53(15) . . . . ? S1 O2 C1 C2 -78.04(19) . . . . ? S1 O2 C1 C6 107.01(17) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? O2 C1 C2 C3 -174.80(15) . . . . ? C7 O1 C3 C2 -177.92(16) . . . . ? C7 O1 C3 C4 0.9(3) . . . . ? C1 C2 C3 O1 179.10(15) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? O1 C3 C4 C5 -179.23(15) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? O1 C3 C4 C9 -0.1(2) . . . . ? C2 C3 C4 C9 178.58(16) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C9 C4 C5 C6 -178.58(16) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? O2 C1 C6 C5 174.80(15) . . . . ? C3 O1 C7 O3 178.81(17) . . . . ? C3 O1 C7 C8 -1.3(3) . . . . ? O3 C7 C8 C9 -179.1(2) . . . . ? O1 C7 C8 C9 1.0(3) . . . . ? O3 C7 C8 C14 0.6(3) . . . . ? O1 C7 C8 C14 -179.29(16) . . . . ? C7 C8 C9 C4 -0.3(3) . . . . ? C14 C8 C9 C4 -179.98(16) . . . . ? C7 C8 C9 C10 179.08(17) . . . . ? C14 C8 C9 C10 -0.6(3) . . . . ? C3 C4 C9 C8 -0.1(2) . . . . ? C5 C4 C9 C8 178.87(16) . . . . ? C3 C4 C9 C10 -179.50(16) . . . . ? C5 C4 C9 C10 -0.5(3) . . . . ? C8 C9 C10 C11 64.9(2) . . . . ? C4 C9 C10 C11 -115.75(19) . . . . ? C9 C10 C11 C12 -79.9(3) . . . . ? C10 C11 C12 C13 62.5(3) . . . . ? C11 C12 C13 C14 -62.0(3) . . . . ? C9 C8 C14 C13 -63.6(3) . . . . ? C7 C8 C14 C13 116.7(2) . . . . ? C12 C13 C14 C8 77.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 HN1 O1S 0.90(3) 1.89(3) 2.782(3) 172(3) 3_655 N1 HN2 O3 0.78(3) 2.21(3) 2.971(3) 166(3) 3_765 #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-10-18 at 14:14:49 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : bn33b_solvat_dmso1_sgs struct data_bn33b_solvat_dmso1_sgs _database_code_depnum_ccdc_archive 'CCDC 849367' #TrackingRef '- BN_DMSO_I_CCDC849367.cif' _audit_creation_date 2011-10-18T14:14:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H21 N1 O6 S2' _chemical_formula_sum 'C16 H21 N O6 S2' _chemical_formula_weight 387.46 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 7.8650(19) _cell_length_b 26.831(7) _cell_length_c 8.552(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1804.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_unetI/netI 0.0445 _diffrn_reflns_number 9962 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3676 _reflns_number_gt 2789 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. The hydrogen atoms of the amine function were located by restrainning their position using a DFIX command : "DFIX 0.9 N1 H1N" and "DFIX 0.9 N1 H2N" ; _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^)+(0.0601P)^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_number_reflns 3676 _refine_ls_number_parameters 266 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(8) _refine_diff_density_max 0.196 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 S1S S 0.30039(13) -0.47764(4) 0.32819(12) 0.0531(4) Uani 0.830(3) 1 d P A 1 C1S C 0.1478(18) -0.5214(5) 0.3791(17) 0.119(5) Uani 0.830(3) 1 d P A 1 H1S1 H 0.1196 -0.5178 0.4877 0.178 Uiso 0.830(3) 1 calc PR A 1 H1S2 H 0.1916 -0.5543 0.3609 0.178 Uiso 0.830(3) 1 calc PR A 1 H1S3 H 0.0477 -0.5164 0.3168 0.178 Uiso 0.830(3) 1 calc PR A 1 C2S C 0.3216(15) -0.4964(4) 0.1288(10) 0.090(3) Uani 0.830(3) 1 d P A 1 H2S1 H 0.2117 -0.4967 0.08 0.135 Uiso 0.830(3) 1 calc PR A 1 H2S2 H 0.3704 -0.5291 0.1243 0.135 Uiso 0.830(3) 1 calc PR A 1 H2S3 H 0.3942 -0.4733 0.0749 0.135 Uiso 0.830(3) 1 calc PR A 1 S1C S 0.1717(9) -0.4777(3) 0.2442(10) 0.088(3) Uani 0.170(3) 1 d P A 2 C1C C 0.163(6) -0.5248(15) 0.400(4) 0.040(7) Uani 0.170(3) 1 d P A 2 H1C1 H 0.264 -0.5227 0.4624 0.061 Uiso 0.170(3) 1 calc PR A 2 H1C2 H 0.1558 -0.5574 0.3536 0.061 Uiso 0.170(3) 1 calc PR A 2 H1C3 H 0.065 -0.519 0.4639 0.061 Uiso 0.170(3) 1 calc PR A 2 C2C C 0.362(9) -0.496(2) 0.168(8) 0.15(3) Uani 0.170(3) 1 d P A 2 H2C1 H 0.4335 -0.5082 0.2497 0.218 Uiso 0.170(3) 1 calc PR A 2 H2C2 H 0.4154 -0.4681 0.1174 0.218 Uiso 0.170(3) 1 calc PR A 2 H2C3 H 0.3429 -0.522 0.0923 0.218 Uiso 0.170(3) 1 calc PR A 2 O1S O 0.2087(3) -0.42880(8) 0.3208(3) 0.0707(7) Uani 1 1 d . . . S1 S 0.31710(10) -0.39909(3) -0.26141(9) 0.0501(2) Uani 1 1 d . . . O1 O 0.3373(2) -0.29532(7) 0.2905(2) 0.0444(5) Uani 1 1 d . . . O2 O 0.1598(3) -0.37158(8) -0.1780(3) 0.0560(6) Uani 1 1 d . . . O3 O 0.4389(3) -0.26688(8) 0.5103(2) 0.0606(6) Uani 1 1 d . . . O4 O 0.2554(4) -0.44803(7) -0.2855(3) 0.0754(7) Uani 1 1 d . . . O5 O 0.4621(3) -0.39058(9) -0.1670(3) 0.0740(7) Uani 1 1 d . . . N1 N 0.3426(4) -0.37408(11) -0.4247(3) 0.0554(7) Uani 1 1 d D . . H1N H 0.394(4) -0.3454(9) -0.434(5) 0.079(12) Uiso 1 1 d D . . H2N H 0.289(4) -0.3888(11) -0.502(3) 0.066(11) Uiso 1 1 d D . . C1 C 0.1942(3) -0.32768(11) -0.0937(3) 0.0455(7) Uani 1 1 d . . . C2 C 0.2474(4) -0.33205(10) 0.0586(3) 0.0424(6) Uani 1 1 d . . . H2 H 0.2605 -0.3631 0.1052 0.051 Uiso 1 1 calc R . . C3 C 0.2805(3) -0.28903(10) 0.1398(3) 0.0386(6) Uani 1 1 d . . . C4 C 0.2600(4) -0.24156(9) 0.0762(3) 0.0391(6) Uani 1 1 d . . . C5 C 0.1978(4) -0.23928(11) -0.0768(4) 0.0502(7) Uani 1 1 d . . . H5 H 0.1778 -0.2083 -0.1222 0.06 Uiso 1 1 calc R . . C6 C 0.1655(4) -0.28189(11) -0.1618(4) 0.0529(7) Uani 1 1 d . . . H6 H 0.1248 -0.2798 -0.2637 0.063 Uiso 1 1 calc R . . C7 C 0.3868(4) -0.25614(10) 0.3808(3) 0.0430(7) Uani 1 1 d . . . C8 C 0.3742(3) -0.20610(9) 0.3158(3) 0.0405(6) Uani 1 1 d . . . C9 C 0.3098(3) -0.19887(11) 0.1720(3) 0.0406(7) Uani 1 1 d . . . C10 C 0.2897(4) -0.14638(11) 0.1080(4) 0.0543(8) Uani 1 1 d . . . H10A H 0.2494 -0.1483 0.0009 0.065 Uiso 1 1 calc R . . H10B H 0.4 -0.1302 0.1067 0.065 Uiso 1 1 calc R . . C11 C 0.1667(4) -0.11479(12) 0.2029(5) 0.0623(10) Uani 1 1 d . . . H11A H 0.125 -0.0881 0.1368 0.075 Uiso 1 1 calc R . . H11B H 0.07 -0.1353 0.2312 0.075 Uiso 1 1 calc R . . C12 C 0.2390(5) -0.09214(12) 0.3500(5) 0.0738(11) Uani 1 1 d . . . H12A H 0.1535 -0.0706 0.3959 0.089 Uiso 1 1 calc R . . H12B H 0.3352 -0.0714 0.3216 0.089 Uiso 1 1 calc R . . C13 C 0.2971(5) -0.12916(13) 0.4740(5) 0.0720(11) Uani 1 1 d . . . H13A H 0.1998 -0.1487 0.5073 0.086 Uiso 1 1 calc R . . H13B H 0.3379 -0.1108 0.5641 0.086 Uiso 1 1 calc R . . C14 C 0.4365(4) -0.16457(11) 0.4198(4) 0.0537(8) Uani 1 1 d . . . H14A H 0.5219 -0.1456 0.3636 0.064 Uiso 1 1 calc R . . H14B H 0.4908 -0.179 0.511 0.064 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 S1S 0.0565(7) 0.0493(6) 0.0533(6) -0.0123(5) -0.0113(5) 0.0050(4) C1S 0.149(10) 0.080(6) 0.127(10) 0.030(6) 0.005(7) -0.015(6) C2S 0.120(8) 0.087(5) 0.064(3) -0.033(3) 0.016(5) 0.007(5) S1C 0.081(5) 0.094(5) 0.090(5) 0.020(4) -0.017(4) -0.008(3) C1C 0.071(19) 0.030(13) 0.020(8) -0.002(9) 0.000(11) -0.007(12) C2C 0.14(4) 0.06(2) 0.24(8) -0.01(3) -0.09(4) -0.03(2) O1S 0.1028(18) 0.0477(12) 0.0616(16) -0.0127(12) -0.0070(14) 0.0132(11) S1 0.0646(5) 0.0481(4) 0.0376(4) -0.0067(4) -0.0054(4) 0.0073(3) O1 0.0598(12) 0.0392(10) 0.0342(10) 0.0003(8) -0.0086(8) -0.0011(8) O2 0.0539(12) 0.0659(13) 0.0481(12) -0.0233(11) -0.0012(11) -0.0079(9) O3 0.0871(17) 0.0542(12) 0.0405(11) 0.0013(9) -0.0211(12) -0.0030(11) O4 0.126(2) 0.0419(12) 0.0588(15) -0.0044(12) 0.0111(15) -0.0033(13) O5 0.0680(15) 0.0974(17) 0.0567(13) -0.0179(13) -0.0204(13) 0.0287(12) N1 0.0711(19) 0.0533(17) 0.0419(14) -0.0027(14) -0.0014(14) -0.0089(14) C1 0.0422(16) 0.0557(18) 0.0387(15) -0.0095(14) 0.0027(13) -0.0058(13) C2 0.0444(16) 0.0426(15) 0.0401(17) -0.0008(12) 0.0038(13) 0.0013(12) C3 0.0394(15) 0.0429(16) 0.0334(14) 0.0004(12) 0.0004(11) -0.0029(12) C4 0.0406(15) 0.0416(15) 0.0350(14) 0.0012(13) 0.0030(12) 0.0052(12) C5 0.060(2) 0.0505(17) 0.0396(15) 0.0091(15) -0.0045(14) 0.0063(14) C6 0.0558(18) 0.071(2) 0.0321(13) -0.0044(15) -0.0076(15) 0.0059(14) C7 0.0463(16) 0.0449(16) 0.0378(15) -0.0048(12) -0.0019(13) -0.0002(12) C8 0.0376(14) 0.0389(14) 0.0450(15) -0.0039(13) 0.0026(13) -0.0034(11) C9 0.0403(15) 0.0389(15) 0.0425(14) 0.0028(12) 0.0045(13) 0.0007(11) C10 0.065(2) 0.0431(17) 0.0547(19) 0.0052(15) 0.0012(16) 0.0035(14) C11 0.0529(19) 0.0501(18) 0.084(3) -0.0015(18) -0.0136(17) 0.0086(14) C12 0.070(2) 0.0569(19) 0.094(3) -0.024(2) -0.014(2) 0.0162(17) C13 0.078(3) 0.071(2) 0.067(2) -0.034(2) -0.0077(19) 0.0098(18) C14 0.0508(19) 0.0518(17) 0.0586(19) -0.0049(15) -0.0141(16) -0.0070(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1S O1S 1.497(2) . ? S1S C1S 1.735(13) . ? S1S C2S 1.785(7) . ? C1S H1S1 0.96 . ? C1S H1S2 0.96 . ? C1S H1S3 0.96 . ? C2S H2S1 0.96 . ? C2S H2S2 0.96 . ? C2S H2S3 0.96 . ? S1C O1S 1.495(8) . ? S1C C2C 1.70(7) . ? S1C C1C 1.84(4) . ? C1C H1C1 0.96 . ? C1C H1C2 0.96 . ? C1C H1C3 0.96 . ? C2C H2C1 0.96 . ? C2C H2C2 0.96 . ? C2C H2C3 0.96 . ? S1 O4 1.415(2) . ? S1 O5 1.416(2) . ? S1 N1 1.563(3) . ? S1 O2 1.608(2) . ? O1 C7 1.361(3) . ? O1 C3 1.374(3) . ? O2 C1 1.407(3) . ? O3 C7 1.216(3) . ? N1 H1N 0.873(18) . ? N1 H2N 0.877(18) . ? C1 C2 1.373(4) . ? C1 C6 1.378(4) . ? C2 C3 1.372(4) . ? C2 H2 0.93 . ? C3 C4 1.394(4) . ? C4 C5 1.398(4) . ? C4 C9 1.462(4) . ? C5 C6 1.378(4) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.456(4) . ? C8 C9 1.344(4) . ? C8 C14 1.507(4) . ? C9 C10 1.519(4) . ? C10 C11 1.521(5) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.509(5) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.523(6) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.523(4) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? 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 O1S S1S C1S 105.7(5) . . ? O1S S1S C2S 104.5(4) . . ? C1S S1S C2S 96.5(6) . . ? O1S S1C C2C 104.6(19) . . ? O1S S1C C1C 107.1(11) . . ? C2C S1C C1C 96(3) . . ? S1C C1C H1C1 109.5 . . ? S1C C1C H1C2 109.5 . . ? H1C1 C1C H1C2 109.5 . . ? S1C C1C H1C3 109.5 . . ? H1C1 C1C H1C3 109.5 . . ? H1C2 C1C H1C3 109.5 . . ? S1C C2C H2C1 109.5 . . ? S1C C2C H2C2 109.5 . . ? H2C1 C2C H2C2 109.5 . . ? S1C C2C H2C3 109.5 . . ? H2C1 C2C H2C3 109.5 . . ? H2C2 C2C H2C3 109.5 . . ? S1C O1S S1S 49.0(3) . . ? O4 S1 O5 120.59(16) . . ? O4 S1 N1 108.19(15) . . ? O5 S1 N1 109.71(16) . . ? O4 S1 O2 103.12(14) . . ? O5 S1 O2 107.02(13) . . ? N1 S1 O2 107.36(14) . . ? C7 O1 C3 122.0(2) . . ? C1 O2 S1 117.61(18) . . ? S1 N1 H1N 121(3) . . ? S1 N1 H2N 115(2) . . ? H1N N1 H2N 123(4) . . ? C2 C1 C6 121.8(3) . . ? C2 C1 O2 118.2(3) . . ? C6 C1 O2 119.9(3) . . ? C3 C2 C1 117.8(3) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 O1 115.7(2) . . ? C2 C3 C4 123.3(2) . . ? O1 C3 C4 121.0(2) . . ? C3 C4 C5 116.5(3) . . ? C3 C4 C9 117.8(2) . . ? C5 C4 C9 125.7(2) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.1(3) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O3 C7 O1 115.5(2) . . ? O3 C7 C8 126.1(3) . . ? O1 C7 C8 118.4(2) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 C14 123.8(3) . . ? C7 C8 C14 115.7(2) . . ? C8 C9 C4 120.1(3) . . ? C8 C9 C10 120.2(3) . . ? C4 C9 C10 119.8(3) . . ? C9 C10 C11 113.0(3) . . ? C9 C10 H10A 109 . . ? C11 C10 H10A 109 . . ? C9 C10 H10B 109 . . ? C11 C10 H10B 109 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 115.5(3) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 115.5(3) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 114.3(3) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C8 C14 C13 114.0(3) . . ? C8 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C8 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? 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 C2C S1C O1S S1S -47(2) . . . . ? C1C S1C O1S S1S 54.1(14) . . . . ? C1S S1S O1S S1C -52.6(7) . . . . ? C2S S1S O1S S1C 48.7(6) . . . . ? O4 S1 O2 C1 160.3(2) . . . . ? O5 S1 O2 C1 32.1(3) . . . . ? N1 S1 O2 C1 -85.6(2) . . . . ? S1 O2 C1 C2 -84.7(3) . . . . ? S1 O2 C1 C6 98.8(3) . . . . ? C6 C1 C2 C3 -3.5(4) . . . . ? O2 C1 C2 C3 -180.0(2) . . . . ? C1 C2 C3 O1 -178.5(2) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C7 O1 C3 C2 175.2(2) . . . . ? C7 O1 C3 C4 -4.5(4) . . . . ? C2 C3 C4 C5 1.8(4) . . . . ? O1 C3 C4 C5 -178.5(2) . . . . ? C2 C3 C4 C9 -176.3(3) . . . . ? O1 C3 C4 C9 3.3(4) . . . . ? C3 C4 C5 C6 -2.6(4) . . . . ? C9 C4 C5 C6 175.3(3) . . . . ? C4 C5 C6 C1 0.4(4) . . . . ? C2 C1 C6 C5 2.8(4) . . . . ? O2 C1 C6 C5 179.2(2) . . . . ? C3 O1 C7 O3 -178.0(3) . . . . ? C3 O1 C7 C8 1.7(4) . . . . ? O3 C7 C8 C9 -178.2(3) . . . . ? O1 C7 C8 C9 2.1(4) . . . . ? O3 C7 C8 C14 1.7(4) . . . . ? O1 C7 C8 C14 -178.0(2) . . . . ? C7 C8 C9 C4 -3.1(4) . . . . ? C14 C8 C9 C4 177.0(3) . . . . ? C7 C8 C9 C10 177.2(2) . . . . ? C14 C8 C9 C10 -2.6(4) . . . . ? C3 C4 C9 C8 0.5(4) . . . . ? C5 C4 C9 C8 -177.5(3) . . . . ? C3 C4 C9 C10 -179.9(2) . . . . ? C5 C4 C9 C10 2.2(4) . . . . ? C8 C9 C10 C11 -62.7(4) . . . . ? C4 C9 C10 C11 117.7(3) . . . . ? C9 C10 C11 C12 80.7(4) . . . . ? C10 C11 C12 C13 -63.2(4) . . . . ? C11 C12 C13 C14 60.1(4) . . . . ? C9 C8 C14 C13 66.1(4) . . . . ? C7 C8 C14 C13 -113.8(3) . . . . ? C12 C13 C14 C8 -76.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.873(18) 2.19(2) 3.026(4) 161(3) 1_554 N1 H2N O1S 0.877(18) 1.96(2) 2.828(4) 169(3) 1_554 #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-10-18 at 14:27:10 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : bn50cmodifie struct data_bn50cmodifie _database_code_depnum_ccdc_archive 'CCDC 849368' #TrackingRef '- BN_DMSO_II_CCDC849368.cif' _audit_creation_date 2011-10-18T14:27:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H19 N1 O6 S2' _chemical_formula_sum 'C16 H19 N O6 S2' _chemical_formula_weight 385.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.713(2) _cell_length_b 9.399(7) _cell_length_c 16.6487(12) _cell_angle_alpha 90 _cell_angle_beta 126.015(9) _cell_angle_gamma 90 _cell_volume 3634(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1371 _diffrn_reflns_av_unetI/netI 0.321 _diffrn_reflns_number 11894 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.56 _diffrn_reflns_theta_full 28.56 _diffrn_measured_fraction_theta_full 0.851 _diffrn_measured_fraction_theta_max 0.851 _reflns_number_total 3949 _reflns_number_gt 1372 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 3949 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2781 _refine_ls_R_factor_gt 0.1572 _refine_ls_wR_factor_ref 0.5387 _refine_ls_wR_factor_gt 0.388 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.517 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.116 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 S1S S 0.20805(13) 0.5757(4) 0.1369(3) 0.0943(13) Uani 1 1 d . . . O1S O 0.2139(4) 0.5214(12) 0.2274(8) 0.134(4) Uani 1 1 d . . . C1S C 0.2694(6) 0.6782(14) 0.1798(12) 0.115(5) Uani 1 1 d . . . H1S1 H 0.2688 0.7616 0.2125 0.172 Uiso 1 1 calc R . . H1S2 H 0.2698 0.7059 0.1247 0.172 Uiso 1 1 calc R . . H1S3 H 0.3032 0.6233 0.2258 0.172 Uiso 1 1 calc R . . C2S C 0.2252(6) 0.4239(14) 0.0912(13) 0.114(5) Uani 1 1 d . . . H2S1 H 0.2582 0.3754 0.146 0.172 Uiso 1 1 calc R . . H2S2 H 0.2335 0.456 0.0461 0.172 Uiso 1 1 calc R . . H2S3 H 0.1929 0.36 0.0572 0.172 Uiso 1 1 calc R . . S1 S 0.11132(12) 0.7393(3) 0.2439(2) 0.0730(10) Uani 1 1 d . . . O1 O -0.0859(2) 0.4386(7) 0.1159(5) 0.0645(18) Uani 1 1 d . . . O2 O 0.0705(3) 0.6637(7) 0.1385(5) 0.075(2) Uani 1 1 d . . . O3 O -0.1629(3) 0.3534(7) 0.0975(6) 0.078(2) Uani 1 1 d . . . O4 O 0.0788(4) 0.7592(8) 0.2833(7) 0.089(2) Uani 1 1 d . . . O5 O 0.1316(4) 0.8561(8) 0.2190(6) 0.097(3) Uani 1 1 d . . . N1 N 0.1623(4) 0.6326(9) 0.3100(6) 0.074(2) Uani 1 1 d . . . C1 C 0.0433(4) 0.5393(11) 0.1383(7) 0.067(3) Uani 1 1 d . . . C2 C -0.0081(4) 0.5473(10) 0.1307(7) 0.062(2) Uani 1 1 d . . . H2 H -0.0232 0.6351 0.1304 0.075 Uiso 1 1 calc R . . C3 C -0.0349(4) 0.4271(10) 0.1238(7) 0.055(2) Uani 1 1 d . . . C4 C -0.0144(4) 0.2931(9) 0.1268(7) 0.052(2) Uani 1 1 d . . . C5 C 0.0390(4) 0.2899(10) 0.1371(7) 0.062(3) Uani 1 1 d . . . H5 H 0.055 0.2024 0.1399 0.075 Uiso 1 1 calc R . . C6 C 0.0665(4) 0.4097(11) 0.1428(7) 0.068(3) Uani 1 1 d . . . H6 H 0.1011 0.4045 0.1496 0.082 Uiso 1 1 calc R . . C7 C -0.1196(4) 0.3258(10) 0.1019(7) 0.061(2) Uani 1 1 d . . . C8 C -0.0992(4) 0.1858(10) 0.0995(8) 0.060(2) Uani 1 1 d . . . C9 C -0.0477(4) 0.1724(8) 0.1161(6) 0.049(2) Uani 1 1 d . . . C10 C -0.0266(4) 0.0209(9) 0.1168(7) 0.066(3) Uani 1 1 d . . . H10A H 0.014 0.025 0.1442 0.079 Uiso 1 1 calc R . . H10B H -0.0305 -0.039 0.1599 0.079 Uiso 1 1 calc R . . C11 C -0.0585(4) -0.0448(11) 0.0169(7) 0.069(3) Uani 1 1 d . . . H11A H -0.0346 -0.118 0.0174 0.083 Uiso 1 1 calc R . . H11B H -0.0652 0.0273 -0.0305 0.083 Uiso 1 1 calc R . . C12 C -0.1167(5) -0.1113(14) -0.0192(10) 0.089(4) Uani 1 1 d . . . H12A H -0.1342 -0.1518 -0.0846 0.107 Uiso 1 1 calc R . . H12B H -0.1101 -0.1882 0.0253 0.107 Uiso 1 1 calc R . . C13 C -0.1582(5) -0.0065(12) -0.0241(9) 0.086(4) Uani 1 1 d . . . H13A H -0.194 -0.0563 -0.0505 0.103 Uiso 1 1 calc R . . H13B H -0.1661 0.0662 -0.0721 0.103 Uiso 1 1 calc R . . C14 C -0.1408(5) 0.0699(12) 0.0721(10) 0.086(3) Uani 1 1 d . . . H14A H -0.175 0.1087 0.0628 0.103 Uiso 1 1 calc R . . H14B H -0.1239 0.0014 0.1259 0.103 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 S1S 0.0834(19) 0.103(3) 0.106(2) 0.029(2) 0.0611(18) 0.0216(18) O1S 0.137(8) 0.166(10) 0.155(9) 0.083(8) 0.116(8) 0.049(7) C1S 0.118(10) 0.098(11) 0.144(13) -0.030(10) 0.085(10) -0.032(8) C2S 0.110(10) 0.081(10) 0.156(14) -0.009(9) 0.081(10) 0.002(7) S1 0.0855(18) 0.0541(18) 0.0792(17) -0.0049(14) 0.0483(14) -0.0176(13) O1 0.064(4) 0.047(4) 0.086(4) -0.006(3) 0.046(3) 0.005(3) O2 0.082(4) 0.066(5) 0.066(4) -0.001(3) 0.038(4) -0.022(4) O3 0.074(4) 0.063(5) 0.103(6) 0.000(4) 0.055(4) 0.008(3) O4 0.118(6) 0.054(5) 0.124(7) -0.025(4) 0.087(6) -0.009(4) O5 0.116(6) 0.062(5) 0.094(6) 0.009(4) 0.051(5) -0.005(4) N1 0.091(6) 0.069(6) 0.068(5) -0.001(5) 0.051(5) -0.014(5) C1 0.078(6) 0.060(7) 0.064(5) -0.004(5) 0.042(5) -0.015(5) C2 0.070(5) 0.039(5) 0.072(6) 0.001(5) 0.039(5) 0.003(4) C3 0.064(5) 0.045(5) 0.060(5) -0.007(4) 0.038(4) 0.001(4) C4 0.071(5) 0.027(4) 0.066(5) -0.022(4) 0.044(4) -0.013(4) C5 0.064(5) 0.044(5) 0.077(6) -0.029(5) 0.041(5) -0.006(4) C6 0.061(5) 0.070(7) 0.072(6) -0.027(5) 0.039(4) -0.011(5) C7 0.064(5) 0.046(6) 0.072(6) -0.010(5) 0.039(5) 0.000(5) C8 0.069(5) 0.038(5) 0.075(6) 0.005(4) 0.044(5) 0.003(4) C9 0.073(5) 0.023(4) 0.053(4) 0.002(3) 0.038(4) 0.016(4) C10 0.083(6) 0.033(5) 0.079(6) -0.021(5) 0.047(5) 0.000(4) C11 0.088(6) 0.059(6) 0.063(5) -0.018(5) 0.047(5) -0.008(5) C12 0.095(8) 0.075(8) 0.099(8) -0.028(7) 0.058(7) -0.003(6) C13 0.074(6) 0.068(8) 0.101(8) -0.040(6) 0.043(6) -0.025(5) C14 0.091(7) 0.065(8) 0.117(9) 0.004(7) 0.071(7) 0.008(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1S O1S 1.505(9) . ? S1S C1S 1.749(12) . ? S1S C2S 1.815(14) . ? C1S H1S1 0.96 . ? C1S H1S2 0.96 . ? C1S H1S3 0.96 . ? C2S H2S1 0.96 . ? C2S H2S2 0.96 . ? C2S H2S3 0.96 . ? S1 O5 1.415(8) . ? S1 O4 1.436(9) . ? S1 N1 1.570(9) . ? S1 O2 1.593(7) . ? O1 C7 1.360(10) . ? O1 C3 1.394(10) . ? O2 C1 1.404(11) . ? O3 C7 1.229(10) . ? C1 C6 1.370(14) . ? C1 C2 1.408(14) . ? C2 C3 1.334(12) . ? C2 H2 0.93 . ? C3 C4 1.380(12) . ? C4 C9 1.426(12) . ? C4 C5 1.440(11) . ? C5 C6 1.346(13) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.451(13) . ? C8 C9 1.343(12) . ? C8 C14 1.476(13) . ? C9 C10 1.545(11) . ? C10 C11 1.482(12) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.538(15) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.509(15) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.547(16) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? 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 O1S S1S C1S 106.6(8) . . ? O1S S1S C2S 104.8(7) . . ? C1S S1S C2S 98.5(7) . . ? S1S C1S H1S1 109.5 . . ? S1S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? S1S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? S1S C2S H2S1 109.5 . . ? S1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? S1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? O5 S1 O4 121.6(5) . . ? O5 S1 N1 109.0(5) . . ? O4 S1 N1 110.6(5) . . ? O5 S1 O2 100.7(4) . . ? O4 S1 O2 107.8(5) . . ? N1 S1 O2 105.5(5) . . ? C7 O1 C3 123.9(7) . . ? C1 O2 S1 115.0(6) . . ? C6 C1 O2 119.2(10) . . ? C6 C1 C2 120.3(9) . . ? O2 C1 C2 120.5(9) . . ? C3 C2 C1 119.0(9) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 123.9(9) . . ? C2 C3 O1 117.6(8) . . ? C4 C3 O1 118.5(8) . . ? C3 C4 C9 118.7(8) . . ? C3 C4 C5 115.3(8) . . ? C9 C4 C5 126.0(8) . . ? C6 C5 C4 122.1(8) . . ? C6 C5 H5 119 . . ? C4 C5 H5 119 . . ? C5 C6 C1 119.5(9) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? O3 C7 O1 116.0(8) . . ? O3 C7 C8 126.8(9) . . ? O1 C7 C8 117.0(8) . . ? C9 C8 C7 119.5(8) . . ? C9 C8 C14 126.0(8) . . ? C7 C8 C14 114.4(8) . . ? C8 C9 C4 122.0(7) . . ? C8 C9 C10 117.9(8) . . ? C4 C9 C10 120.1(8) . . ? C11 C10 C9 113.2(8) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 114.9(9) . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 113.4(10) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 118.9(10) . . ? C12 C13 H13A 107.6 . . ? C14 C13 H13A 107.6 . . ? C12 C13 H13B 107.6 . . ? C14 C13 H13B 107.6 . . ? H13A C13 H13B 107 . . ? C8 C14 C13 111.9(10) . . ? C8 C14 H14A 109.2 . . ? C13 C14 H14A 109.2 . . ? C8 C14 H14B 109.2 . . ? C13 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? 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 O5 S1 O2 C1 179.4(8) . . . . ? O4 S1 O2 C1 -52.1(8) . . . . ? N1 S1 O2 C1 66.1(8) . . . . ? S1 O2 C1 C6 -98.1(10) . . . . ? S1 O2 C1 C2 83.8(10) . . . . ? C6 C1 C2 C3 -2.7(15) . . . . ? O2 C1 C2 C3 175.4(8) . . . . ? C1 C2 C3 C4 2.1(15) . . . . ? C1 C2 C3 O1 -179.7(8) . . . . ? C7 O1 C3 C2 175.6(9) . . . . ? C7 O1 C3 C4 -6.2(13) . . . . ? C2 C3 C4 C9 -178.4(9) . . . . ? O1 C3 C4 C9 3.5(13) . . . . ? C2 C3 C4 C5 -0.6(14) . . . . ? O1 C3 C4 C5 -178.8(7) . . . . ? C3 C4 C5 C6 -0.3(14) . . . . ? C9 C4 C5 C6 177.2(9) . . . . ? C4 C5 C6 C1 -0.2(16) . . . . ? O2 C1 C6 C5 -176.4(9) . . . . ? C2 C1 C6 C5 1.7(16) . . . . ? C3 O1 C7 O3 179.2(8) . . . . ? C3 O1 C7 C8 2.7(14) . . . . ? O3 C7 C8 C9 -172.7(10) . . . . ? O1 C7 C8 C9 3.4(15) . . . . ? O3 C7 C8 C14 11.0(16) . . . . ? O1 C7 C8 C14 -172.9(9) . . . . ? C7 C8 C9 C4 -6.0(15) . . . . ? C14 C8 C9 C4 169.9(10) . . . . ? C7 C8 C9 C10 177.8(8) . . . . ? C14 C8 C9 C10 -6.3(15) . . . . ? C3 C4 C9 C8 2.5(14) . . . . ? C5 C4 C9 C8 -174.9(9) . . . . ? C3 C4 C9 C10 178.7(8) . . . . ? C5 C4 C9 C10 1.2(14) . . . . ? C8 C9 C10 C11 71.6(12) . . . . ? C4 C9 C10 C11 -104.7(10) . . . . ? C9 C10 C11 C12 -81.3(12) . . . . ? C10 C11 C12 C13 59.0(14) . . . . ? C11 C12 C13 C14 -60.3(15) . . . . ? C9 C8 C14 C13 -57.4(15) . . . . ? C7 C8 C14 C13 118.7(10) . . . . ? C12 C13 C14 C8 77.0(14) . . . . ?