# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2011 data_global _journal_coden_Cambridge 1326 loop_ _publ_author_name 'Cruz-Cabeza, Aurora' 'Day, Graeme' 'Jones, William' _publ_contact_author_name 'Cruz-Cabeza, Aurora' _publ_contact_author_email cruz@ccdc.cam.ac.uk _publ_section_title ; Structure Prediction, Disorder and Dynamics in a DMSO Solvate of Carbamazepine ; # Attachment '- crystal_structures.cif' data_CBZDMSO_280K _database_code_depnum_ccdc_archive 'CCDC 819036' #TrackingRef '- crystal_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C2 H6 O S' _chemical_formula_sum 'C17 H18 N2 O2 S' _chemical_formula_weight 314.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4105(3) _cell_length_b 8.9753(3) _cell_length_c 12.2407(4) _cell_angle_alpha 94.259(2) _cell_angle_beta 94.526(3) _cell_angle_gamma 100.200(2) _cell_volume 795.54(5) _cell_formula_units_Z 2 _cell_measurement_temperature 280(2) _cell_measurement_reflns_used 3722 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 1.003 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The DMSO molecule is disordered over two sites, ratio 0.667 : 0.333 ; _diffrn_ambient_temperature 280(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6622 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3609 _reflns_number_gt 2581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1789P] 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 SHELXL _refine_ls_extinction_coef 0.043(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3609 _refine_ls_number_parameters 242 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.02832(18) 0.87311(15) 0.10765(10) 0.0541(4) Uani 1 1 d . . . N1 N 0.16653(19) 0.93655(15) 0.26276(11) 0.0400(3) Uani 1 1 d . . . C1 C 0.4990(2) 1.00191(19) 0.31392(13) 0.0419(4) Uani 1 1 d . . . C2 C 0.5330(3) 0.8685(2) 0.24792(15) 0.0482(4) Uani 1 1 d . . . H2 H 0.6419 0.8802 0.2140 0.058 Uiso 1 1 calc R . . N2 N 0.1605(2) 1.10227(17) 0.12600(12) 0.0518(4) Uani 1 1 d . . . H2A H 0.1174 1.1264 0.0638 0.062 Uiso 1 1 calc R . . H2B H 0.2462 1.1648 0.1658 0.062 Uiso 1 1 calc R . . C3 C 0.0942(2) 0.96726(19) 0.16095(13) 0.0398(4) Uani 1 1 d . . . C4 C 0.3229(2) 1.03288(18) 0.32421(13) 0.0393(4) Uani 1 1 d . . . C5 C 0.6474(3) 1.1010(2) 0.37311(16) 0.0518(5) Uani 1 1 d . . . H5 H 0.7665 1.0844 0.3661 0.062 Uiso 1 1 calc R . . C6 C 0.6209(3) 1.2224(2) 0.44137(15) 0.0570(5) Uani 1 1 d . . . H6 H 0.7216 1.2867 0.4801 0.068 Uiso 1 1 calc R . . C7 C 0.2461(2) 0.68451(19) 0.27349(13) 0.0404(4) Uani 1 1 d . . . C8 C 0.0339(3) 0.4868(2) 0.34407(16) 0.0562(5) Uani 1 1 d . . . H8 H 0.0026 0.3865 0.3605 0.067 Uiso 1 1 calc R . . C9 C 0.4462(3) 1.2489(2) 0.45243(16) 0.0582(5) Uani 1 1 d . . . H9 H 0.4285 1.3306 0.4991 0.070 Uiso 1 1 calc R . . C10 C 0.1246(2) 0.78366(18) 0.29340(13) 0.0387(4) Uani 1 1 d . . . C11 C 0.2960(3) 1.1541(2) 0.39407(15) 0.0498(5) Uani 1 1 d . . . H11 H 0.1776 1.1718 0.4018 0.060 Uiso 1 1 calc R . . C12 C -0.0363(3) 0.7357(2) 0.34123(15) 0.0481(4) Uani 1 1 d . . . H12 H -0.1139 0.8038 0.3567 0.058 Uiso 1 1 calc R . . C13 C 0.4241(3) 0.7318(2) 0.23124(14) 0.0473(4) Uani 1 1 d . . . H13 H 0.4666 0.6584 0.1877 0.057 Uiso 1 1 calc R . . C14 C 0.1955(3) 0.5333(2) 0.29801(15) 0.0493(5) Uani 1 1 d . . . H14 H 0.2719 0.4641 0.2830 0.059 Uiso 1 1 calc R . . C15 C -0.0818(3) 0.5869(2) 0.36603(17) 0.0572(5) Uani 1 1 d . . . H15 H -0.1905 0.5545 0.3975 0.069 Uiso 1 1 calc R . . S1 S 0.67365(12) 0.33041(11) 0.15252(6) 0.0654(3) Uani 0.67 1 d PD A 1 O2 O 0.4981(10) 0.3582(15) 0.1663(7) 0.0642(16) Uani 0.67 1 d PD A 1 C16 C 0.7580(15) 0.4894(15) 0.0667(11) 0.116(4) Uani 0.67 1 d PD A 1 H16A H 0.7091 0.5776 0.0896 0.174 Uiso 0.67 1 calc PR A 1 H16B H 0.7179 0.4585 -0.0094 0.174 Uiso 0.67 1 calc PR A 1 H16C H 0.8901 0.5131 0.0762 0.174 Uiso 0.67 1 calc PR A 1 C17 C 0.6861(17) 0.1838(10) 0.0708(8) 0.126(5) Uani 0.67 1 d PD A 1 H17A H 0.6466 0.0930 0.1059 0.189 Uiso 0.67 1 calc PR A 1 H17B H 0.8110 0.1882 0.0537 0.189 Uiso 0.67 1 calc PR A 1 H17C H 0.6081 0.1830 0.0043 0.189 Uiso 0.67 1 calc PR A 1 S1' S 0.5758(2) 0.33677(19) 0.05824(13) 0.0579(4) Uani 0.33 1 d PD B 2 O2' O 0.459(2) 0.359(3) 0.1400(15) 0.072(4) Uani 0.33 1 d PD B 2 C16' C 0.803(2) 0.459(2) 0.0626(15) 0.081(5) Uani 0.33 1 d PD B 2 H16D H 0.8139 0.5401 0.1197 0.121 Uiso 0.33 1 calc PR B 2 H16E H 0.8171 0.5002 -0.0069 0.121 Uiso 0.33 1 calc PR B 2 H16F H 0.8969 0.3999 0.0774 0.121 Uiso 0.33 1 calc PR B 2 C17' C 0.664(4) 0.166(2) 0.0567(19) 0.138(9) Uani 0.33 1 d PD B 2 H17D H 0.5659 0.0823 0.0626 0.207 Uiso 0.33 1 calc PR B 2 H17E H 0.7559 0.1726 0.1175 0.207 Uiso 0.33 1 calc PR B 2 H17F H 0.7183 0.1505 -0.0110 0.207 Uiso 0.33 1 calc PR B 2 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 O1 0.0531(8) 0.0552(8) 0.0468(7) 0.0161(6) -0.0125(6) -0.0068(6) N1 0.0413(8) 0.0377(7) 0.0402(7) 0.0098(6) -0.0055(6) 0.0071(6) C1 0.0435(10) 0.0432(9) 0.0389(9) 0.0104(7) -0.0018(7) 0.0070(7) C2 0.0438(10) 0.0571(11) 0.0462(10) 0.0091(8) 0.0082(8) 0.0127(9) N2 0.0551(10) 0.0488(9) 0.0475(9) 0.0176(7) -0.0099(7) 0.0001(7) C3 0.0376(9) 0.0428(9) 0.0404(9) 0.0096(7) 0.0019(7) 0.0098(7) C4 0.0439(10) 0.0361(9) 0.0378(8) 0.0100(6) -0.0025(7) 0.0071(7) C5 0.0460(11) 0.0529(11) 0.0543(11) 0.0136(9) -0.0058(8) 0.0040(8) C6 0.0663(14) 0.0513(11) 0.0449(10) 0.0101(8) -0.0132(9) -0.0065(9) C7 0.0474(10) 0.0401(9) 0.0335(8) 0.0034(6) 0.0002(7) 0.0097(7) C8 0.0672(13) 0.0403(10) 0.0615(12) 0.0175(8) 0.0046(10) 0.0066(9) C9 0.0813(16) 0.0422(10) 0.0476(11) -0.0008(8) -0.0004(10) 0.0067(10) C10 0.0424(9) 0.0378(9) 0.0358(8) 0.0068(6) -0.0035(7) 0.0085(7) C11 0.0585(12) 0.0451(10) 0.0479(10) 0.0049(8) 0.0030(8) 0.0156(9) C12 0.0459(10) 0.0484(10) 0.0530(11) 0.0127(8) 0.0041(8) 0.0141(8) C13 0.0536(11) 0.0484(10) 0.0427(10) 0.0022(7) 0.0092(8) 0.0163(9) C14 0.0607(12) 0.0393(10) 0.0491(10) 0.0048(7) 0.0012(8) 0.0141(8) C15 0.0532(12) 0.0550(12) 0.0656(13) 0.0222(9) 0.0101(9) 0.0068(9) S1 0.0550(5) 0.0879(6) 0.0461(4) 0.0060(4) 0.0051(3) -0.0060(4) O2 0.053(4) 0.066(2) 0.074(3) -0.002(2) 0.022(3) 0.007(3) C16 0.079(7) 0.128(6) 0.140(7) 0.001(4) 0.063(5) -0.005(4) C17 0.197(10) 0.121(6) 0.109(6) 0.053(5) 0.091(7) 0.112(7) S1' 0.0554(9) 0.0673(10) 0.0499(8) -0.0002(7) 0.0084(7) 0.0096(7) O2' 0.046(5) 0.061(4) 0.105(10) 0.004(7) 0.009(5) 0.002(4) C16' 0.050(7) 0.113(11) 0.071(7) 0.023(7) 0.030(5) -0.024(7) C17' 0.171(19) 0.166(17) 0.077(9) -0.036(10) -0.017(10) 0.064(13) _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 O1 C3 1.232(2) . ? N1 C3 1.383(2) . ? N1 C10 1.437(2) . ? N1 C4 1.438(2) . ? C1 C4 1.395(2) . ? C1 C5 1.399(2) . ? C1 C2 1.465(3) . ? C2 C13 1.335(3) . ? C2 H2 0.9300 . ? N2 C3 1.339(2) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C4 C11 1.385(2) . ? C5 C6 1.375(3) . ? C5 H5 0.9300 . ? C6 C9 1.373(3) . ? C6 H6 0.9300 . ? C7 C10 1.396(2) . ? C7 C14 1.404(2) . ? C7 C13 1.459(3) . ? C8 C15 1.374(3) . ? C8 C14 1.375(3) . ? C8 H8 0.9300 . ? C9 C11 1.386(3) . ? C9 H9 0.9300 . ? C10 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C15 1.380(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? S1 O2 1.388(7) . ? S1 C17 1.613(8) . ? S1 C16 1.881(11) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? S1' O2' 1.399(17) . ? S1' C17' 1.769(17) . ? S1' C16' 1.833(15) . ? C16' H16D 0.9600 . ? C16' H16E 0.9600 . ? C16' H16F 0.9600 . ? C17' H17D 0.9600 . ? C17' H17E 0.9600 . ? C17' H17F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C10 118.34(13) . . ? C3 N1 C4 123.03(13) . . ? C10 N1 C4 115.79(12) . . ? C4 C1 C5 117.61(17) . . ? C4 C1 C2 122.92(16) . . ? C5 C1 C2 119.43(17) . . ? C13 C2 C1 126.92(17) . . ? C13 C2 H2 116.5 . . ? C1 C2 H2 116.5 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O1 C3 N2 122.91(15) . . ? O1 C3 N1 119.88(15) . . ? N2 C3 N1 117.19(15) . . ? C11 C4 C1 120.92(16) . . ? C11 C4 N1 119.43(16) . . ? C1 C4 N1 119.64(15) . . ? C6 C5 C1 121.43(19) . . ? C6 C5 H5 119.3 . . ? C1 C5 H5 119.3 . . ? C9 C6 C5 120.08(18) . . ? C9 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C10 C7 C14 118.02(16) . . ? C10 C7 C13 123.07(16) . . ? C14 C7 C13 118.89(16) . . ? C15 C8 C14 120.70(18) . . ? C15 C8 H8 119.7 . . ? C14 C8 H8 119.7 . . ? C6 C9 C11 120.07(19) . . ? C6 C9 H9 120.0 . . ? C11 C9 H9 120.0 . . ? C12 C10 C7 120.70(16) . . ? C12 C10 N1 119.83(15) . . ? C7 C10 N1 119.47(15) . . ? C4 C11 C9 119.84(19) . . ? C4 C11 H11 120.1 . . ? C9 C11 H11 120.1 . . ? C15 C12 C10 120.13(17) . . ? C15 C12 H12 119.9 . . ? C10 C12 H12 119.9 . . ? C2 C13 C7 127.45(17) . . ? C2 C13 H13 116.3 . . ? C7 C13 H13 116.3 . . ? C8 C14 C7 120.54(17) . . ? C8 C14 H14 119.7 . . ? C7 C14 H14 119.7 . . ? C8 C15 C12 119.85(19) . . ? C8 C15 H15 120.1 . . ? C12 C15 H15 120.1 . . ? O2 S1 C17 116.3(6) . . ? O2 S1 C16 99.9(6) . . ? C17 S1 C16 101.1(5) . . ? O2' S1' C17' 116.1(14) . . ? O2' S1' C16' 120.1(11) . . ? C17' S1' C16' 94.2(13) . . ? S1' C16' H16D 109.5 . . ? S1' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? S1' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? S1' C17' H17D 109.5 . . ? S1' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? S1' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C1 C2 C13 -32.6(3) . . . . ? C5 C1 C2 C13 144.99(19) . . . . ? C10 N1 C3 O1 12.9(2) . . . . ? C4 N1 C3 O1 172.97(16) . . . . ? C10 N1 C3 N2 -168.45(15) . . . . ? C4 N1 C3 N2 -8.4(2) . . . . ? C5 C1 C4 C11 -2.5(2) . . . . ? C2 C1 C4 C11 175.09(16) . . . . ? C5 C1 C4 N1 178.37(15) . . . . ? C2 C1 C4 N1 -4.0(2) . . . . ? C3 N1 C4 C11 87.3(2) . . . . ? C10 N1 C4 C11 -112.18(17) . . . . ? C3 N1 C4 C1 -93.63(19) . . . . ? C10 N1 C4 C1 66.9(2) . . . . ? C4 C1 C5 C6 1.7(3) . . . . ? C2 C1 C5 C6 -175.99(16) . . . . ? C1 C5 C6 C9 -0.2(3) . . . . ? C5 C6 C9 C11 -0.6(3) . . . . ? C14 C7 C10 C12 3.3(2) . . . . ? C13 C7 C10 C12 -175.11(16) . . . . ? C14 C7 C10 N1 -176.06(14) . . . . ? C13 C7 C10 N1 5.5(2) . . . . ? C3 N1 C10 C12 -85.5(2) . . . . ? C4 N1 C10 C12 113.03(18) . . . . ? C3 N1 C10 C7 93.90(18) . . . . ? C4 N1 C10 C7 -67.6(2) . . . . ? C1 C4 C11 C9 1.9(3) . . . . ? N1 C4 C11 C9 -179.05(16) . . . . ? C6 C9 C11 C4 -0.3(3) . . . . ? C7 C10 C12 C15 -2.5(3) . . . . ? N1 C10 C12 C15 176.89(16) . . . . ? C1 C2 C13 C7 0.8(3) . . . . ? C10 C7 C13 C2 30.8(3) . . . . ? C14 C7 C13 C2 -147.56(19) . . . . ? C15 C8 C14 C7 0.6(3) . . . . ? C10 C7 C14 C8 -2.4(3) . . . . ? C13 C7 C14 C8 176.10(17) . . . . ? C14 C8 C15 C12 0.3(3) . . . . ? C10 C12 C15 C8 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.220 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.056 data_CBZDMSO_200K _database_code_depnum_ccdc_archive 'CCDC 819037' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C2 H6 O S' _chemical_formula_sum 'C17 H18 N2 O2 S' _chemical_formula_weight 314.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3605(2) _cell_length_b 8.9292(3) _cell_length_c 12.2136(3) _cell_angle_alpha 94.491(2) _cell_angle_beta 94.715(2) _cell_angle_gamma 100.070(2) _cell_volume 784.16(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4651 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The DMSO molecule is disordered over two sites, ratio 0.62 : 0.38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7801 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3573 _reflns_number_gt 2896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.1940P] 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 SHELXL _refine_ls_extinction_coef 0.24(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3573 _refine_ls_number_parameters 243 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 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 O1 O -0.03032(19) 0.87253(15) 0.10712(11) 0.0399(4) Uani 1 1 d . . . N1 N 0.1649(2) 0.93744(16) 0.26404(12) 0.0299(3) Uani 1 1 d . . . C1 C 0.5007(2) 1.00228(19) 0.31402(14) 0.0306(4) Uani 1 1 d . . . C2 C 0.5337(3) 0.8683(2) 0.24707(15) 0.0347(4) Uani 1 1 d . . . H2 H 0.6446 0.8801 0.2114 0.042 Uiso 1 1 calc R . . N2 N 0.1603(2) 1.10367(18) 0.12662(13) 0.0381(4) Uani 1 1 d . . . H2A H 0.1162 1.1286 0.0627 0.046 Uiso 1 1 calc R . . H2B H 0.2483 1.1679 0.1679 0.046 Uiso 1 1 calc R . . C3 C 0.0931(2) 0.9676(2) 0.16111(14) 0.0294(4) Uani 1 1 d . . . C4 C 0.3229(2) 1.03338(19) 0.32536(14) 0.0294(4) Uani 1 1 d . . . C5 C 0.6513(3) 1.1023(2) 0.37303(16) 0.0378(4) Uani 1 1 d . . . H5 H 0.7735 1.0854 0.3648 0.045 Uiso 1 1 calc R . . C6 C 0.6262(3) 1.2243(2) 0.44255(16) 0.0402(5) Uani 1 1 d . . . H6 H 0.7303 1.2898 0.4822 0.048 Uiso 1 1 calc R . . C7 C 0.2450(2) 0.68364(19) 0.27358(13) 0.0298(4) Uani 1 1 d . . . C8 C 0.0317(3) 0.4844(2) 0.34424(17) 0.0415(5) Uani 1 1 d . . . H8 H -0.0003 0.3815 0.3609 0.050 Uiso 1 1 calc R . . C9 C 0.4492(3) 1.2515(2) 0.45470(16) 0.0420(5) Uani 1 1 d . . . H9 H 0.4318 1.3355 0.5029 0.050 Uiso 1 1 calc R . . C10 C 0.1224(2) 0.78351(19) 0.29409(14) 0.0296(4) Uani 1 1 d . . . C11 C 0.2970(3) 1.1561(2) 0.39635(16) 0.0363(4) Uani 1 1 d . . . H11 H 0.1754 1.1745 0.4048 0.044 Uiso 1 1 calc R . . C12 C -0.0393(3) 0.7360(2) 0.34212(16) 0.0359(4) Uani 1 1 d . . . H12 H -0.1187 0.8064 0.3582 0.043 Uiso 1 1 calc R . . C13 C 0.4234(3) 0.7303(2) 0.23079(14) 0.0339(4) Uani 1 1 d . . . H13 H 0.4665 0.6543 0.1863 0.041 Uiso 1 1 calc R . . C14 C 0.1945(3) 0.5312(2) 0.29778(15) 0.0357(4) Uani 1 1 d . . . H14 H 0.2731 0.4600 0.2821 0.043 Uiso 1 1 calc R . . C15 C -0.0854(3) 0.5861(2) 0.36678(18) 0.0425(5) Uani 1 1 d . . . H15 H -0.1970 0.5532 0.3990 0.051 Uiso 1 1 calc R . . S1 S 0.67616(12) 0.32453(11) 0.15363(7) 0.0461(3) Uani 0.62 1 d PD A 1 O2 O 0.4932(19) 0.3608(16) 0.1647(12) 0.052(2) Uani 0.62 1 d PD A 1 C16 C 0.7539(10) 0.4918(9) 0.0596(8) 0.081(2) Uani 0.62 1 d PD A 1 H16A H 0.6459 0.5353 0.0349 0.121 Uiso 0.62 1 calc PR A 1 H16B H 0.8072 0.4510 -0.0047 0.121 Uiso 0.62 1 calc PR A 1 H16C H 0.8468 0.5716 0.1023 0.121 Uiso 0.62 1 calc PR A 1 C17 C 0.697(2) 0.1860(13) 0.0702(9) 0.105(5) Uani 0.62 1 d PD A 1 H17A H 0.6538 0.0898 0.1014 0.158 Uiso 0.62 1 calc PR A 1 H17B H 0.8279 0.1929 0.0571 0.158 Uiso 0.62 1 calc PR A 1 H17C H 0.6232 0.1894 0.0003 0.158 Uiso 0.62 1 calc PR A 1 S1' S 0.5732(2) 0.33628(17) 0.05744(11) 0.0450(4) Uani 0.38 1 d PD B 2 O2' O 0.475(3) 0.356(3) 0.152(2) 0.065(5) Uani 0.38 1 d PD B 2 C16' C 0.8089(12) 0.4509(14) 0.0704(9) 0.054(2) Uani 0.38 1 d PD B 2 H16D H 0.8282 0.5197 0.1386 0.081 Uiso 0.38 1 calc PR B 2 H16E H 0.8240 0.5111 0.0070 0.081 Uiso 0.38 1 calc PR B 2 H16F H 0.8999 0.3828 0.0727 0.081 Uiso 0.38 1 calc PR B 2 C17' C 0.646(4) 0.160(2) 0.0591(14) 0.084(5) Uani 0.38 1 d PD B 2 H17D H 0.5401 0.0803 0.0694 0.126 Uiso 0.38 1 calc PR B 2 H17E H 0.7429 0.1652 0.1198 0.126 Uiso 0.38 1 calc PR B 2 H17F H 0.6944 0.1352 -0.0111 0.126 Uiso 0.38 1 calc PR B 2 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 O1 0.0394(8) 0.0407(7) 0.0345(7) 0.0113(5) -0.0078(5) -0.0045(6) N1 0.0312(8) 0.0277(7) 0.0304(8) 0.0073(5) -0.0021(6) 0.0047(6) C1 0.0326(9) 0.0308(8) 0.0288(8) 0.0079(6) 0.0005(7) 0.0056(7) C2 0.0318(9) 0.0409(10) 0.0332(9) 0.0068(7) 0.0059(7) 0.0091(7) N2 0.0402(9) 0.0366(8) 0.0347(8) 0.0131(6) -0.0060(6) -0.0004(7) C3 0.0273(8) 0.0330(9) 0.0290(8) 0.0066(6) 0.0017(6) 0.0077(7) C4 0.0338(9) 0.0270(8) 0.0273(8) 0.0071(6) -0.0018(6) 0.0055(7) C5 0.0330(10) 0.0398(10) 0.0392(10) 0.0102(8) -0.0030(7) 0.0028(8) C6 0.0475(11) 0.0362(10) 0.0315(9) 0.0065(7) -0.0076(8) -0.0036(8) C7 0.0337(9) 0.0309(9) 0.0247(8) 0.0017(6) 0.0005(6) 0.0069(7) C8 0.0471(11) 0.0313(9) 0.0469(11) 0.0118(8) 0.0049(9) 0.0053(8) C9 0.0581(13) 0.0325(9) 0.0336(10) 0.0000(7) 0.0013(8) 0.0063(9) C10 0.0332(9) 0.0294(8) 0.0259(8) 0.0053(6) -0.0022(6) 0.0064(7) C11 0.0409(10) 0.0334(9) 0.0364(10) 0.0046(7) 0.0027(7) 0.0114(8) C12 0.0333(10) 0.0366(9) 0.0400(10) 0.0088(7) 0.0032(7) 0.0107(7) C13 0.0383(10) 0.0365(9) 0.0296(9) 0.0026(7) 0.0072(7) 0.0126(8) C14 0.0442(11) 0.0296(9) 0.0351(9) 0.0039(7) 0.0036(8) 0.0111(8) C15 0.0387(11) 0.0421(11) 0.0493(12) 0.0162(9) 0.0097(9) 0.0066(8) S1 0.0376(5) 0.0635(6) 0.0323(4) 0.0052(3) 0.0050(3) -0.0054(4) O2 0.060(6) 0.041(4) 0.057(3) -0.001(2) 0.022(3) 0.006(4) C16 0.047(4) 0.080(5) 0.116(6) 0.009(4) 0.046(4) -0.002(3) C17 0.150(12) 0.119(7) 0.093(7) 0.060(6) 0.067(7) 0.101(9) S1' 0.0426(7) 0.0519(8) 0.0401(7) -0.0001(6) 0.0080(5) 0.0077(6) O2' 0.035(4) 0.052(7) 0.103(13) -0.014(7) 0.033(6) -0.009(4) C16' 0.032(5) 0.081(7) 0.048(4) 0.015(4) 0.012(3) 0.002(4) C17' 0.089(9) 0.123(11) 0.047(6) -0.012(6) 0.022(5) 0.038(7) _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 O1 C3 1.235(2) . ? N1 C3 1.388(2) . ? N1 C4 1.434(2) . ? N1 C10 1.439(2) . ? C1 C4 1.400(2) . ? C1 C5 1.402(3) . ? C1 C2 1.463(3) . ? C2 C13 1.342(3) . ? C2 H2 0.9500 . ? N2 C3 1.342(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C4 C11 1.393(3) . ? C5 C6 1.376(3) . ? C5 H5 0.9500 . ? C6 C9 1.384(3) . ? C6 H6 0.9500 . ? C7 C10 1.398(2) . ? C7 C14 1.408(2) . ? C7 C13 1.458(3) . ? C8 C14 1.381(3) . ? C8 C15 1.385(3) . ? C8 H8 0.9500 . ? C9 C11 1.389(3) . ? C9 H9 0.9500 . ? C10 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C15 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? S1 O2 1.453(12) . ? S1 C17 1.577(10) . ? S1 C16 1.989(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? S1' O2' 1.429(18) . ? S1' C17' 1.750(15) . ? S1' C16' 1.841(10) . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? 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 C3 N1 C4 122.87(14) . . ? C3 N1 C10 118.03(14) . . ? C4 N1 C10 115.87(13) . . ? C4 C1 C5 117.69(17) . . ? C4 C1 C2 122.77(16) . . ? C5 C1 C2 119.50(17) . . ? C13 C2 C1 126.72(17) . . ? C13 C2 H2 116.6 . . ? C1 C2 H2 116.6 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O1 C3 N2 123.16(15) . . ? O1 C3 N1 119.82(15) . . ? N2 C3 N1 117.00(15) . . ? C11 C4 C1 120.82(16) . . ? C11 C4 N1 119.33(16) . . ? C1 C4 N1 119.85(15) . . ? C6 C5 C1 121.57(19) . . ? C6 C5 H5 119.2 . . ? C1 C5 H5 119.2 . . ? C5 C6 C9 120.01(18) . . ? C5 C6 H6 120.0 . . ? C9 C6 H6 120.0 . . ? C10 C7 C14 118.06(17) . . ? C10 C7 C13 123.32(16) . . ? C14 C7 C13 118.60(16) . . ? C14 C8 C15 120.60(17) . . ? C14 C8 H8 119.7 . . ? C15 C8 H8 119.7 . . ? C6 C9 C11 119.97(18) . . ? C6 C9 H9 120.0 . . ? C11 C9 H9 120.0 . . ? C12 C10 C7 120.98(16) . . ? C12 C10 N1 119.72(16) . . ? C7 C10 N1 119.30(16) . . ? C9 C11 C4 119.89(18) . . ? C9 C11 H11 120.1 . . ? C4 C11 H11 120.1 . . ? C10 C12 C15 120.10(17) . . ? C10 C12 H12 120.0 . . ? C15 C12 H12 120.0 . . ? C2 C13 C7 127.48(16) . . ? C2 C13 H13 116.3 . . ? C7 C13 H13 116.3 . . ? C8 C14 C7 120.45(17) . . ? C8 C14 H14 119.8 . . ? C7 C14 H14 119.8 . . ? C8 C15 C12 119.74(19) . . ? C8 C15 H15 120.1 . . ? C12 C15 H15 120.1 . . ? O2 S1 C17 119.3(9) . . ? O2 S1 C16 94.8(5) . . ? C17 S1 C16 98.0(5) . . ? O2' S1' C17' 107.5(12) . . ? O2' S1' C16' 113.8(12) . . ? C17' S1' C16' 95.2(9) . . ? S1' C16' H16D 109.5 . . ? S1' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? S1' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? S1' C17' H17D 109.5 . . ? S1' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? S1' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C1 C2 C13 -32.8(3) . . . . ? C5 C1 C2 C13 144.84(19) . . . . ? C4 N1 C3 O1 172.19(16) . . . . ? C10 N1 C3 O1 13.3(2) . . . . ? C4 N1 C3 N2 -9.5(2) . . . . ? C10 N1 C3 N2 -168.41(16) . . . . ? C5 C1 C4 C11 -2.5(2) . . . . ? C2 C1 C4 C11 175.24(16) . . . . ? C5 C1 C4 N1 178.00(15) . . . . ? C2 C1 C4 N1 -4.3(2) . . . . ? C3 N1 C4 C11 88.4(2) . . . . ? C10 N1 C4 C11 -112.28(18) . . . . ? C3 N1 C4 C1 -92.0(2) . . . . ? C10 N1 C4 C1 67.2(2) . . . . ? C4 C1 C5 C6 2.0(3) . . . . ? C2 C1 C5 C6 -175.81(16) . . . . ? C1 C5 C6 C9 -0.6(3) . . . . ? C5 C6 C9 C11 -0.3(3) . . . . ? C14 C7 C10 C12 3.3(3) . . . . ? C13 C7 C10 C12 -175.35(17) . . . . ? C14 C7 C10 N1 -176.29(15) . . . . ? C13 C7 C10 N1 5.1(2) . . . . ? C3 N1 C10 C12 -86.5(2) . . . . ? C4 N1 C10 C12 113.21(19) . . . . ? C3 N1 C10 C7 93.13(19) . . . . ? C4 N1 C10 C7 -67.2(2) . . . . ? C6 C9 C11 C4 -0.2(3) . . . . ? C1 C4 C11 C9 1.7(3) . . . . ? N1 C4 C11 C9 -178.83(16) . . . . ? C7 C10 C12 C15 -2.5(3) . . . . ? N1 C10 C12 C15 177.10(16) . . . . ? C1 C2 C13 C7 1.5(3) . . . . ? C10 C7 C13 C2 30.6(3) . . . . ? C14 C7 C13 C2 -148.01(19) . . . . ? C15 C8 C14 C7 0.6(3) . . . . ? C10 C7 C14 C8 -2.4(3) . . . . ? C13 C7 C14 C8 176.35(17) . . . . ? C14 C8 C15 C12 0.3(3) . . . . ? C10 C12 C15 C8 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.576 _refine_diff_density_min -0.632 _refine_diff_density_rms 0.197 data_CBZDMSO_150K _database_code_depnum_ccdc_archive 'CCDC 819038' #TrackingRef '- crystal_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C2 H6 O S' _chemical_formula_sum 'C17 H18 N2 O2 S' _chemical_formula_weight 314.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3605(2) _cell_length_b 8.9292(3) _cell_length_c 12.2136(3) _cell_angle_alpha 94.491(2) _cell_angle_beta 94.715(2) _cell_angle_gamma 100.070(2) _cell_volume 784.16(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4651 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The DMSO molecule is disordered over two sites, ratio 0.62 : 0.38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7801 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3573 _reflns_number_gt 2896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.1940P] 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 SHELXL _refine_ls_extinction_coef 0.24(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3573 _refine_ls_number_parameters 243 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 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 O1 O -0.03032(19) 0.87253(15) 0.10712(11) 0.0399(4) Uani 1 1 d . . . N1 N 0.1649(2) 0.93744(16) 0.26404(12) 0.0299(3) Uani 1 1 d . . . C1 C 0.5007(2) 1.00228(19) 0.31402(14) 0.0306(4) Uani 1 1 d . . . C2 C 0.5337(3) 0.8683(2) 0.24707(15) 0.0347(4) Uani 1 1 d . . . H2 H 0.6446 0.8801 0.2114 0.042 Uiso 1 1 calc R . . N2 N 0.1603(2) 1.10367(18) 0.12662(13) 0.0381(4) Uani 1 1 d . . . H2A H 0.1162 1.1286 0.0627 0.046 Uiso 1 1 calc R . . H2B H 0.2483 1.1679 0.1679 0.046 Uiso 1 1 calc R . . C3 C 0.0931(2) 0.9676(2) 0.16111(14) 0.0294(4) Uani 1 1 d . . . C4 C 0.3229(2) 1.03338(19) 0.32536(14) 0.0294(4) Uani 1 1 d . . . C5 C 0.6513(3) 1.1023(2) 0.37303(16) 0.0378(4) Uani 1 1 d . . . H5 H 0.7735 1.0854 0.3648 0.045 Uiso 1 1 calc R . . C6 C 0.6262(3) 1.2243(2) 0.44255(16) 0.0402(5) Uani 1 1 d . . . H6 H 0.7303 1.2898 0.4822 0.048 Uiso 1 1 calc R . . C7 C 0.2450(2) 0.68364(19) 0.27358(13) 0.0298(4) Uani 1 1 d . . . C8 C 0.0317(3) 0.4844(2) 0.34424(17) 0.0415(5) Uani 1 1 d . . . H8 H -0.0003 0.3815 0.3609 0.050 Uiso 1 1 calc R . . C9 C 0.4492(3) 1.2515(2) 0.45470(16) 0.0420(5) Uani 1 1 d . . . H9 H 0.4318 1.3355 0.5029 0.050 Uiso 1 1 calc R . . C10 C 0.1224(2) 0.78351(19) 0.29409(14) 0.0296(4) Uani 1 1 d . . . C11 C 0.2970(3) 1.1561(2) 0.39635(16) 0.0363(4) Uani 1 1 d . . . H11 H 0.1754 1.1745 0.4048 0.044 Uiso 1 1 calc R . . C12 C -0.0393(3) 0.7360(2) 0.34212(16) 0.0359(4) Uani 1 1 d . . . H12 H -0.1187 0.8064 0.3582 0.043 Uiso 1 1 calc R . . C13 C 0.4234(3) 0.7303(2) 0.23079(14) 0.0339(4) Uani 1 1 d . . . H13 H 0.4665 0.6543 0.1863 0.041 Uiso 1 1 calc R . . C14 C 0.1945(3) 0.5312(2) 0.29778(15) 0.0357(4) Uani 1 1 d . . . H14 H 0.2731 0.4600 0.2821 0.043 Uiso 1 1 calc R . . C15 C -0.0854(3) 0.5861(2) 0.36678(18) 0.0425(5) Uani 1 1 d . . . H15 H -0.1970 0.5532 0.3990 0.051 Uiso 1 1 calc R . . S1 S 0.67616(12) 0.32453(11) 0.15363(7) 0.0461(3) Uani 0.62 1 d PD A 1 O2 O 0.4932(19) 0.3608(16) 0.1647(12) 0.052(2) Uani 0.62 1 d PD A 1 C16 C 0.7539(10) 0.4918(9) 0.0596(8) 0.081(2) Uani 0.62 1 d PD A 1 H16A H 0.6459 0.5353 0.0349 0.121 Uiso 0.62 1 calc PR A 1 H16B H 0.8072 0.4510 -0.0047 0.121 Uiso 0.62 1 calc PR A 1 H16C H 0.8468 0.5716 0.1023 0.121 Uiso 0.62 1 calc PR A 1 C17 C 0.697(2) 0.1860(13) 0.0702(9) 0.105(5) Uani 0.62 1 d PD A 1 H17A H 0.6538 0.0898 0.1014 0.158 Uiso 0.62 1 calc PR A 1 H17B H 0.8279 0.1929 0.0571 0.158 Uiso 0.62 1 calc PR A 1 H17C H 0.6232 0.1894 0.0003 0.158 Uiso 0.62 1 calc PR A 1 S1' S 0.5732(2) 0.33628(17) 0.05744(11) 0.0450(4) Uani 0.38 1 d PD B 2 O2' O 0.475(3) 0.356(3) 0.152(2) 0.065(5) Uani 0.38 1 d PD B 2 C16' C 0.8089(12) 0.4509(14) 0.0704(9) 0.054(2) Uani 0.38 1 d PD B 2 H16D H 0.8282 0.5197 0.1386 0.081 Uiso 0.38 1 calc PR B 2 H16E H 0.8240 0.5111 0.0070 0.081 Uiso 0.38 1 calc PR B 2 H16F H 0.8999 0.3828 0.0727 0.081 Uiso 0.38 1 calc PR B 2 C17' C 0.646(4) 0.160(2) 0.0591(14) 0.084(5) Uani 0.38 1 d PD B 2 H17D H 0.5401 0.0803 0.0694 0.126 Uiso 0.38 1 calc PR B 2 H17E H 0.7429 0.1652 0.1198 0.126 Uiso 0.38 1 calc PR B 2 H17F H 0.6944 0.1352 -0.0111 0.126 Uiso 0.38 1 calc PR B 2 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 O1 0.0394(8) 0.0407(7) 0.0345(7) 0.0113(5) -0.0078(5) -0.0045(6) N1 0.0312(8) 0.0277(7) 0.0304(8) 0.0073(5) -0.0021(6) 0.0047(6) C1 0.0326(9) 0.0308(8) 0.0288(8) 0.0079(6) 0.0005(7) 0.0056(7) C2 0.0318(9) 0.0409(10) 0.0332(9) 0.0068(7) 0.0059(7) 0.0091(7) N2 0.0402(9) 0.0366(8) 0.0347(8) 0.0131(6) -0.0060(6) -0.0004(7) C3 0.0273(8) 0.0330(9) 0.0290(8) 0.0066(6) 0.0017(6) 0.0077(7) C4 0.0338(9) 0.0270(8) 0.0273(8) 0.0071(6) -0.0018(6) 0.0055(7) C5 0.0330(10) 0.0398(10) 0.0392(10) 0.0102(8) -0.0030(7) 0.0028(8) C6 0.0475(11) 0.0362(10) 0.0315(9) 0.0065(7) -0.0076(8) -0.0036(8) C7 0.0337(9) 0.0309(9) 0.0247(8) 0.0017(6) 0.0005(6) 0.0069(7) C8 0.0471(11) 0.0313(9) 0.0469(11) 0.0118(8) 0.0049(9) 0.0053(8) C9 0.0581(13) 0.0325(9) 0.0336(10) 0.0000(7) 0.0013(8) 0.0063(9) C10 0.0332(9) 0.0294(8) 0.0259(8) 0.0053(6) -0.0022(6) 0.0064(7) C11 0.0409(10) 0.0334(9) 0.0364(10) 0.0046(7) 0.0027(7) 0.0114(8) C12 0.0333(10) 0.0366(9) 0.0400(10) 0.0088(7) 0.0032(7) 0.0107(7) C13 0.0383(10) 0.0365(9) 0.0296(9) 0.0026(7) 0.0072(7) 0.0126(8) C14 0.0442(11) 0.0296(9) 0.0351(9) 0.0039(7) 0.0036(8) 0.0111(8) C15 0.0387(11) 0.0421(11) 0.0493(12) 0.0162(9) 0.0097(9) 0.0066(8) S1 0.0376(5) 0.0635(6) 0.0323(4) 0.0052(3) 0.0050(3) -0.0054(4) O2 0.060(6) 0.041(4) 0.057(3) -0.001(2) 0.022(3) 0.006(4) C16 0.047(4) 0.080(5) 0.116(6) 0.009(4) 0.046(4) -0.002(3) C17 0.150(12) 0.119(7) 0.093(7) 0.060(6) 0.067(7) 0.101(9) S1' 0.0426(7) 0.0519(8) 0.0401(7) -0.0001(6) 0.0080(5) 0.0077(6) O2' 0.035(4) 0.052(7) 0.103(13) -0.014(7) 0.033(6) -0.009(4) C16' 0.032(5) 0.081(7) 0.048(4) 0.015(4) 0.012(3) 0.002(4) C17' 0.089(9) 0.123(11) 0.047(6) -0.012(6) 0.022(5) 0.038(7) _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 O1 C3 1.235(2) . ? N1 C3 1.388(2) . ? N1 C4 1.434(2) . ? N1 C10 1.439(2) . ? C1 C4 1.400(2) . ? C1 C5 1.402(3) . ? C1 C2 1.463(3) . ? C2 C13 1.342(3) . ? C2 H2 0.9500 . ? N2 C3 1.342(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? C4 C11 1.393(3) . ? C5 C6 1.376(3) . ? C5 H5 0.9500 . ? C6 C9 1.384(3) . ? C6 H6 0.9500 . ? C7 C10 1.398(2) . ? C7 C14 1.408(2) . ? C7 C13 1.458(3) . ? C8 C14 1.381(3) . ? C8 C15 1.385(3) . ? C8 H8 0.9500 . ? C9 C11 1.389(3) . ? C9 H9 0.9500 . ? C10 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C15 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? S1 O2 1.453(12) . ? S1 C17 1.577(10) . ? S1 C16 1.989(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? S1' O2' 1.429(18) . ? S1' C17' 1.750(15) . ? S1' C16' 1.841(10) . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? 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 C3 N1 C4 122.87(14) . . ? C3 N1 C10 118.03(14) . . ? C4 N1 C10 115.87(13) . . ? C4 C1 C5 117.69(17) . . ? C4 C1 C2 122.77(16) . . ? C5 C1 C2 119.50(17) . . ? C13 C2 C1 126.72(17) . . ? C13 C2 H2 116.6 . . ? C1 C2 H2 116.6 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O1 C3 N2 123.16(15) . . ? O1 C3 N1 119.82(15) . . ? N2 C3 N1 117.00(15) . . ? C11 C4 C1 120.82(16) . . ? C11 C4 N1 119.33(16) . . ? C1 C4 N1 119.85(15) . . ? C6 C5 C1 121.57(19) . . ? C6 C5 H5 119.2 . . ? C1 C5 H5 119.2 . . ? C5 C6 C9 120.01(18) . . ? C5 C6 H6 120.0 . . ? C9 C6 H6 120.0 . . ? C10 C7 C14 118.06(17) . . ? C10 C7 C13 123.32(16) . . ? C14 C7 C13 118.60(16) . . ? C14 C8 C15 120.60(17) . . ? C14 C8 H8 119.7 . . ? C15 C8 H8 119.7 . . ? C6 C9 C11 119.97(18) . . ? C6 C9 H9 120.0 . . ? C11 C9 H9 120.0 . . ? C12 C10 C7 120.98(16) . . ? C12 C10 N1 119.72(16) . . ? C7 C10 N1 119.30(16) . . ? C9 C11 C4 119.89(18) . . ? C9 C11 H11 120.1 . . ? C4 C11 H11 120.1 . . ? C10 C12 C15 120.10(17) . . ? C10 C12 H12 120.0 . . ? C15 C12 H12 120.0 . . ? C2 C13 C7 127.48(16) . . ? C2 C13 H13 116.3 . . ? C7 C13 H13 116.3 . . ? C8 C14 C7 120.45(17) . . ? C8 C14 H14 119.8 . . ? C7 C14 H14 119.8 . . ? C8 C15 C12 119.74(19) . . ? C8 C15 H15 120.1 . . ? C12 C15 H15 120.1 . . ? O2 S1 C17 119.3(9) . . ? O2 S1 C16 94.8(5) . . ? C17 S1 C16 98.0(5) . . ? O2' S1' C17' 107.5(12) . . ? O2' S1' C16' 113.8(12) . . ? C17' S1' C16' 95.2(9) . . ? S1' C16' H16D 109.5 . . ? S1' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? S1' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? S1' C17' H17D 109.5 . . ? S1' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? S1' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C1 C2 C13 -32.8(3) . . . . ? C5 C1 C2 C13 144.84(19) . . . . ? C4 N1 C3 O1 172.19(16) . . . . ? C10 N1 C3 O1 13.3(2) . . . . ? C4 N1 C3 N2 -9.5(2) . . . . ? C10 N1 C3 N2 -168.41(16) . . . . ? C5 C1 C4 C11 -2.5(2) . . . . ? C2 C1 C4 C11 175.24(16) . . . . ? C5 C1 C4 N1 178.00(15) . . . . ? C2 C1 C4 N1 -4.3(2) . . . . ? C3 N1 C4 C11 88.4(2) . . . . ? C10 N1 C4 C11 -112.28(18) . . . . ? C3 N1 C4 C1 -92.0(2) . . . . ? C10 N1 C4 C1 67.2(2) . . . . ? C4 C1 C5 C6 2.0(3) . . . . ? C2 C1 C5 C6 -175.81(16) . . . . ? C1 C5 C6 C9 -0.6(3) . . . . ? C5 C6 C9 C11 -0.3(3) . . . . ? C14 C7 C10 C12 3.3(3) . . . . ? C13 C7 C10 C12 -175.35(17) . . . . ? C14 C7 C10 N1 -176.29(15) . . . . ? C13 C7 C10 N1 5.1(2) . . . . ? C3 N1 C10 C12 -86.5(2) . . . . ? C4 N1 C10 C12 113.21(19) . . . . ? C3 N1 C10 C7 93.13(19) . . . . ? C4 N1 C10 C7 -67.2(2) . . . . ? C6 C9 C11 C4 -0.2(3) . . . . ? C1 C4 C11 C9 1.7(3) . . . . ? N1 C4 C11 C9 -178.83(16) . . . . ? C7 C10 C12 C15 -2.5(3) . . . . ? N1 C10 C12 C15 177.10(16) . . . . ? C1 C2 C13 C7 1.5(3) . . . . ? C10 C7 C13 C2 30.6(3) . . . . ? C14 C7 C13 C2 -148.01(19) . . . . ? C15 C8 C14 C7 0.6(3) . . . . ? C10 C7 C14 C8 -2.4(3) . . . . ? C13 C7 C14 C8 176.35(17) . . . . ? C14 C8 C15 C12 0.3(3) . . . . ? C10 C12 C15 C8 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.576 _refine_diff_density_min -0.632 _refine_diff_density_rms 0.197 data_CBZDMSO_110K _database_code_depnum_ccdc_archive 'CCDC 819039' #TrackingRef '- crystal_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C2 H6 O S' _chemical_formula_sum 'C17 H18 N2 O2 S' _chemical_formula_weight 314.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8708(2) _cell_length_b 12.1901(3) _cell_length_c 14.6128(4) _cell_angle_alpha 94.9700(10) _cell_angle_beta 100.2170(10) _cell_angle_gamma 95.0360(10) _cell_volume 1540.67(7) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 12900 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The two DMSO molecules are each disordered over two sites. For each site, the occupancies are in the ratio 0.94:0.06 ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16689 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7002 _reflns_number_gt 5318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.2252P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7002 _refine_ls_number_parameters 431 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1_1 S 1.33646(6) 0.55665(4) 0.78637(3) 0.02461(14) Uani 0.94 1 d P A 1 O2_1 O 1.3673(3) 0.6621(4) 0.7438(4) 0.0316(7) Uani 0.94 1 d P A 1 C16_1 C 1.2128(3) 0.5853(2) 0.86725(19) 0.0368(5) Uani 0.94 1 d P A 1 H16A_1 H 1.1120 0.5991 0.8331 0.055 Uiso 0.94 1 calc PR A 1 H16B_1 H 1.2580 0.6509 0.9101 0.055 Uiso 0.94 1 calc PR A 1 H16C_1 H 1.2006 0.5218 0.9030 0.055 Uiso 0.94 1 calc PR A 1 C17_1 C 1.5051(3) 0.5439(2) 0.87038(17) 0.0334(5) Uani 0.94 1 d P A 1 H17A_1 H 1.5884 0.5247 0.8379 0.050 Uiso 0.94 1 calc PR A 1 H17B_1 H 1.4828 0.4856 0.9097 0.050 Uiso 0.94 1 calc PR A 1 H17C_1 H 1.5367 0.6144 0.9096 0.050 Uiso 0.94 1 calc PR A 1 S1'_1 S 1.3156(8) 0.6543(6) 0.8403(5) 0.0198(9) Uiso 0.06 1 d P B 2 O2'_1 O 1.339(7) 0.664(7) 0.743(6) 0.0198(9) Uiso 0.06 1 d P B 2 C16'_1 C 1.149(4) 0.559(3) 0.826(2) 0.0198(9) Uiso 0.06 1 d P B 2 H16D_1 H 1.0598 0.5922 0.7954 0.030 Uiso 0.06 1 calc PR B 2 H16E_1 H 1.1325 0.5398 0.8878 0.030 Uiso 0.06 1 calc PR B 2 H16F_1 H 1.1632 0.4917 0.7881 0.030 Uiso 0.06 1 calc PR B 2 C17'_1 C 1.460(4) 0.574(3) 0.897(2) 0.0198(9) Uiso 0.06 1 d P B 2 H17D_1 H 1.5615 0.6163 0.9074 0.030 Uiso 0.06 1 calc PR B 2 H17E_1 H 1.4610 0.5046 0.8576 0.030 Uiso 0.06 1 calc PR B 2 H17F_1 H 1.4357 0.5562 0.9576 0.030 Uiso 0.06 1 calc PR B 2 O1_1 O 1.13038(14) 0.39373(10) 1.01864(9) 0.0233(3) Uani 1 1 d . . . N1_1 N 1.06753(16) 0.23510(11) 0.91993(10) 0.0178(3) Uani 1 1 d . . . C1_1 C 1.0029(2) 0.18472(13) 0.75040(12) 0.0188(4) Uani 1 1 d . . . N2_1 N 0.89983(17) 0.37238(12) 0.91893(11) 0.0220(3) Uani 1 1 d . . . H2A_1 H 0.8745 0.4366 0.9403 0.026 Uiso 1 1 calc R . . H2B_1 H 0.8361 0.3304 0.8738 0.026 Uiso 1 1 calc R . . C2_1 C 1.1386(2) 0.25286(14) 0.73446(13) 0.0205(4) Uani 1 1 d . . . H2_1 H 1.1267 0.2882 0.6786 0.025 Uiso 1 1 calc R . . C3_1 C 1.0358(2) 0.33842(13) 0.95510(12) 0.0176(4) Uani 1 1 d . . . C4_1 C 0.97095(19) 0.17258(13) 0.83973(12) 0.0177(4) Uani 1 1 d . . . C5_1 C 0.9016(2) 0.12588(14) 0.67377(13) 0.0220(4) Uani 1 1 d . . . H5_1 H 0.9188 0.1347 0.6124 0.026 Uiso 1 1 calc R . . C6_1 C 0.7776(2) 0.05553(14) 0.68547(14) 0.0235(4) Uani 1 1 d . . . H6_1 H 0.7110 0.0160 0.6325 0.028 Uiso 1 1 calc R . . C7_1 C 1.3244(2) 0.22857(13) 0.88090(12) 0.0186(4) Uani 1 1 d . . . C8_1 C 1.5260(2) 0.16200(15) 0.98997(13) 0.0237(4) Uani 1 1 d . . . H8_1 H 1.6302 0.1473 1.0068 0.028 Uiso 1 1 calc R . . C9_1 C 0.7500(2) 0.04241(15) 0.77475(14) 0.0245(4) Uani 1 1 d . . . H9_1 H 0.6650 -0.0064 0.7830 0.029 Uiso 1 1 calc R . . C10_1 C 1.2229(2) 0.20725(13) 0.94202(12) 0.0178(4) Uani 1 1 d . . . C11_1 C 0.8469(2) 0.10086(14) 0.85180(13) 0.0215(4) Uani 1 1 d . . . H11_1 H 0.8285 0.0918 0.9129 0.026 Uiso 1 1 calc R . . C12_1 C 1.2713(2) 0.16070(14) 1.02448(13) 0.0213(4) Uani 1 1 d . . . H12_1 H 1.2003 0.1440 1.0642 0.026 Uiso 1 1 calc R . . C13_1 C 1.2773(2) 0.27064(13) 0.79021(13) 0.0202(4) Uani 1 1 d . . . H13_1 H 1.3540 0.3156 0.7686 0.024 Uiso 1 1 calc R . . C14_1 C 1.4780(2) 0.20647(14) 0.90714(13) 0.0216(4) Uani 1 1 d . . . H14_1 H 1.5497 0.2222 0.8676 0.026 Uiso 1 1 calc R . . C15_1 C 1.4230(2) 0.13866(15) 1.04877(13) 0.0242(4) Uani 1 1 d . . . H15_1 H 1.4564 0.1077 1.1054 0.029 Uiso 1 1 calc R . . S1_2 S 1.69593(6) 0.34677(4) 0.65856(3) 0.02339(14) Uani 0.94 1 d P C 1 O2_2 O 1.6505(4) 0.33557(19) 0.75155(19) 0.0292(6) Uani 0.94 1 d P C 1 C16_2 C 1.8619(3) 0.44608(18) 0.67881(18) 0.0312(5) Uani 0.94 1 d P C 1 H16A_2 H 1.9474 0.4172 0.7185 0.047 Uiso 0.94 1 calc PR C 1 H16B_2 H 1.8384 0.5152 0.7101 0.047 Uiso 0.94 1 calc PR C 1 H16C_2 H 1.8911 0.4603 0.6190 0.047 Uiso 0.94 1 calc PR C 1 C17_2 C 1.5639(3) 0.42947(19) 0.59649(16) 0.0335(5) Uani 0.94 1 d P C 1 H17A_2 H 1.4611 0.3884 0.5810 0.050 Uiso 0.94 1 calc PR C 1 H17B_2 H 1.5982 0.4471 0.5388 0.050 Uiso 0.94 1 calc PR C 1 H17C_2 H 1.5600 0.4982 0.6357 0.050 Uiso 0.94 1 calc PR C 1 S1'_2 S 1.6654(8) 0.4434(6) 0.7143(5) 0.0198(9) Uiso 0.06 1 d P D 2 O2'_2 O 1.649(7) 0.360(4) 0.765(4) 0.0198(9) Uiso 0.06 1 d P D 2 C16'_2 C 1.798(4) 0.417(3) 0.641(2) 0.0198(9) Uiso 0.06 1 d P D 2 H16D_2 H 1.8987 0.4112 0.6788 0.030 Uiso 0.06 1 calc PR D 2 H16E_2 H 1.8055 0.4776 0.6014 0.030 Uiso 0.06 1 calc PR D 2 H16F_2 H 1.7621 0.3473 0.6010 0.030 Uiso 0.06 1 calc PR D 2 C17'_2 C 1.502(4) 0.454(3) 0.629(2) 0.0198(9) Uiso 0.06 1 d P D 2 H17D_2 H 1.4251 0.4888 0.6589 0.030 Uiso 0.06 1 calc PR D 2 H17E_2 H 1.4589 0.3795 0.6004 0.030 Uiso 0.06 1 calc PR D 2 H17F_2 H 1.5313 0.4985 0.5816 0.030 Uiso 0.06 1 calc PR D 2 N1_2 N 0.94043(16) 0.76493(11) 0.58283(10) 0.0174(3) Uani 1 1 d . . . O1_2 O 0.87180(14) 0.60557(10) 0.48569(9) 0.0232(3) Uani 1 1 d . . . C1_2 C 1.0078(2) 0.81443(14) 0.75215(12) 0.0190(4) Uani 1 1 d . . . N2_2 N 1.10900(17) 0.62866(12) 0.57861(11) 0.0223(3) Uani 1 1 d . . . H2A_2 H 1.1333 0.5645 0.5563 0.027 Uiso 1 1 calc R . . H2B_2 H 1.1754 0.6712 0.6219 0.027 Uiso 1 1 calc R . . C2_2 C 0.8722(2) 0.74686(14) 0.76876(12) 0.0196(4) Uani 1 1 d . . . H2_2 H 0.8844 0.7107 0.8243 0.024 Uiso 1 1 calc R . . C3_2 C 0.9702(2) 0.66165(13) 0.54648(12) 0.0177(4) Uani 1 1 d . . . C4_2 C 1.03857(19) 0.82677(13) 0.66280(12) 0.0180(4) Uani 1 1 d . . . C5_2 C 1.1089(2) 0.87421(14) 0.82882(13) 0.0212(4) Uani 1 1 d . . . H5_2 H 1.0923 0.8652 0.8903 0.025 Uiso 1 1 calc R . . C6_2 C 1.2317(2) 0.94556(14) 0.81672(13) 0.0230(4) Uani 1 1 d . . . H6_2 H 1.2979 0.9858 0.8695 0.028 Uiso 1 1 calc R . . C7_2 C 0.6851(2) 0.77437(13) 0.62368(12) 0.0181(4) Uani 1 1 d . . . C8_2 C 0.4850(2) 0.84596(14) 0.51705(13) 0.0222(4) Uani 1 1 d . . . H8_2 H 0.3817 0.8628 0.5013 0.027 Uiso 1 1 calc R . . C9_2 C 1.2583(2) 0.95846(15) 0.72704(14) 0.0240(4) Uani 1 1 d . . . H9_2 H 1.3424 1.0078 0.7184 0.029 Uiso 1 1 calc R . . C10_2 C 0.78625(19) 0.79477(13) 0.56185(12) 0.0180(4) Uani 1 1 d . . . C11_2 C 1.1618(2) 0.89916(14) 0.65035(13) 0.0215(4) Uani 1 1 d . . . H11_2 H 1.1798 0.9080 0.5891 0.026 Uiso 1 1 calc R . . C12_2 C 0.7381(2) 0.84273(14) 0.48030(13) 0.0208(4) Uani 1 1 d . . . H12_2 H 0.8085 0.8582 0.4399 0.025 Uiso 1 1 calc R . . C13_2 C 0.7327(2) 0.73087(13) 0.71363(12) 0.0198(4) Uani 1 1 d . . . H13_2 H 0.6558 0.6862 0.7353 0.024 Uiso 1 1 calc R . . C14_2 C 0.5326(2) 0.79944(14) 0.59908(13) 0.0209(4) Uani 1 1 d . . . H14_2 H 0.4614 0.7843 0.6391 0.025 Uiso 1 1 calc R . . C15_2 C 0.5875(2) 0.86813(15) 0.45759(13) 0.0235(4) Uani 1 1 d . . . H15_2 H 0.5545 0.9006 0.4016 0.028 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_1 0.0259(3) 0.0252(3) 0.0219(3) 0.00442(18) 0.0027(2) -0.00029(19) O2_1 0.0250(19) 0.0368(9) 0.0324(9) 0.0176(7) 0.0001(14) -0.0037(14) C16_1 0.0352(14) 0.0361(13) 0.0426(15) 0.0074(10) 0.0174(12) -0.0002(10) C17_1 0.0326(13) 0.0373(12) 0.0309(13) 0.0062(9) 0.0030(10) 0.0102(10) O1_1 0.0233(7) 0.0215(6) 0.0217(7) -0.0039(5) -0.0031(5) 0.0051(5) N1_1 0.0163(7) 0.0201(7) 0.0169(8) 0.0000(5) 0.0023(6) 0.0046(6) C1_1 0.0178(9) 0.0186(8) 0.0203(9) 0.0015(6) 0.0031(7) 0.0055(6) N2_1 0.0216(8) 0.0216(7) 0.0208(8) -0.0034(6) -0.0014(6) 0.0073(6) C2_1 0.0250(9) 0.0198(8) 0.0182(9) 0.0036(6) 0.0062(7) 0.0044(7) C3_1 0.0206(9) 0.0186(8) 0.0150(9) 0.0036(6) 0.0054(7) 0.0040(7) C4_1 0.0161(8) 0.0178(8) 0.0189(9) -0.0009(6) 0.0019(7) 0.0052(6) C5_1 0.0238(9) 0.0233(9) 0.0192(9) -0.0004(7) 0.0039(7) 0.0068(7) C6_1 0.0205(9) 0.0205(9) 0.0264(10) -0.0035(7) -0.0021(8) 0.0038(7) C7_1 0.0185(9) 0.0156(8) 0.0206(9) -0.0006(6) 0.0024(7) 0.0011(6) C8_1 0.0164(9) 0.0274(9) 0.0270(10) 0.0024(7) 0.0014(8) 0.0069(7) C9_1 0.0193(9) 0.0201(9) 0.0332(11) 0.0008(7) 0.0039(8) 0.0007(7) C10_1 0.0170(8) 0.0156(8) 0.0197(9) -0.0010(6) 0.0021(7) 0.0026(6) C11_1 0.0196(9) 0.0225(9) 0.0239(10) 0.0014(7) 0.0077(8) 0.0034(7) C12_1 0.0217(9) 0.0232(9) 0.0198(9) 0.0020(7) 0.0055(7) 0.0052(7) C13_1 0.0220(9) 0.0167(8) 0.0230(10) 0.0033(7) 0.0067(8) 0.0011(7) C14_1 0.0178(9) 0.0213(9) 0.0256(10) 0.0016(7) 0.0043(7) 0.0017(7) C15_1 0.0233(10) 0.0278(10) 0.0223(10) 0.0055(7) 0.0017(8) 0.0095(7) S1_2 0.0282(3) 0.0208(2) 0.0198(3) 0.00271(17) -0.0004(2) 0.00379(19) O2_2 0.0240(8) 0.0383(17) 0.0248(14) 0.0089(10) 0.0025(9) 0.0000(11) C16_2 0.0317(12) 0.0263(11) 0.0370(13) 0.0066(9) 0.0094(11) 0.0004(9) C17_2 0.0397(13) 0.0310(11) 0.0282(12) 0.0058(9) -0.0036(10) 0.0117(10) N1_2 0.0142(7) 0.0200(7) 0.0176(8) -0.0010(5) 0.0022(6) 0.0039(5) O1_2 0.0223(7) 0.0225(6) 0.0217(7) -0.0037(5) -0.0025(5) 0.0052(5) C1_2 0.0187(9) 0.0189(8) 0.0202(9) 0.0018(6) 0.0038(7) 0.0060(7) N2_2 0.0194(8) 0.0211(7) 0.0248(8) -0.0031(6) 0.0001(6) 0.0060(6) C2_2 0.0222(9) 0.0198(8) 0.0179(9) 0.0033(6) 0.0049(7) 0.0043(7) C3_2 0.0190(9) 0.0195(8) 0.0157(9) 0.0029(6) 0.0045(7) 0.0042(7) C4_2 0.0158(8) 0.0176(8) 0.0202(9) -0.0007(6) 0.0021(7) 0.0048(6) C5_2 0.0216(9) 0.0236(9) 0.0183(9) -0.0001(7) 0.0024(7) 0.0067(7) C6_2 0.0201(9) 0.0209(9) 0.0252(10) -0.0029(7) -0.0022(8) 0.0045(7) C7_2 0.0180(9) 0.0157(8) 0.0202(9) 0.0001(6) 0.0038(7) 0.0003(6) C8_2 0.0171(9) 0.0251(9) 0.0242(10) 0.0014(7) 0.0019(7) 0.0054(7) C9_2 0.0180(9) 0.0217(9) 0.0312(11) 0.0014(7) 0.0031(8) 0.0014(7) C10_2 0.0159(8) 0.0174(8) 0.0196(9) -0.0028(6) 0.0024(7) 0.0014(6) C11_2 0.0204(9) 0.0224(9) 0.0228(10) 0.0023(7) 0.0055(8) 0.0045(7) C12_2 0.0214(9) 0.0242(9) 0.0172(9) 0.0003(7) 0.0054(7) 0.0036(7) C13_2 0.0215(9) 0.0173(8) 0.0215(9) 0.0028(6) 0.0064(7) 0.0008(7) C14_2 0.0177(9) 0.0205(8) 0.0243(10) 0.0007(7) 0.0050(7) 0.0012(7) C15_2 0.0248(10) 0.0267(9) 0.0195(9) 0.0041(7) 0.0021(8) 0.0076(7) _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_1 O2_1 1.500(6) . ? S1_1 C16_1 1.783(2) . ? S1_1 C17_1 1.787(2) . ? C16_1 H16A_1 0.9800 . ? C16_1 H16B_1 0.9800 . ? C16_1 H16C_1 0.9800 . ? C17_1 H17A_1 0.9800 . ? C17_1 H17B_1 0.9800 . ? C17_1 H17C_1 0.9800 . ? S1'_1 O2'_1 1.49(9) . ? S1'_1 C16'_1 1.77(3) . ? S1'_1 C17'_1 1.81(3) . ? C16'_1 H16D_1 0.9800 . ? C16'_1 H16E_1 0.9800 . ? C16'_1 H16F_1 0.9800 . ? C17'_1 H17D_1 0.9800 . ? C17'_1 H17E_1 0.9800 . ? C17'_1 H17F_1 0.9800 . ? O1_1 C3_1 1.239(2) . ? N1_1 C3_1 1.390(2) . ? N1_1 C10_1 1.436(2) . ? N1_1 C4_1 1.436(2) . ? C1_1 C4_1 1.401(2) . ? C1_1 C5_1 1.402(2) . ? C1_1 C2_1 1.466(2) . ? N2_1 C3_1 1.344(2) . ? N2_1 H2A_1 0.8800 . ? N2_1 H2B_1 0.8800 . ? C2_1 C13_1 1.339(3) . ? C2_1 H2_1 0.9500 . ? C4_1 C11_1 1.390(2) . ? C5_1 C6_1 1.379(3) . ? C5_1 H5_1 0.9500 . ? C6_1 C9_1 1.389(3) . ? C6_1 H6_1 0.9500 . ? C7_1 C10_1 1.400(2) . ? C7_1 C14_1 1.405(2) . ? C7_1 C13_1 1.467(3) . ? C8_1 C14_1 1.383(3) . ? C8_1 C15_1 1.389(3) . ? C8_1 H8_1 0.9500 . ? C9_1 C11_1 1.387(3) . ? C9_1 H9_1 0.9500 . ? C10_1 C12_1 1.391(3) . ? C11_1 H11_1 0.9500 . ? C12_1 C15_1 1.385(3) . ? C12_1 H12_1 0.9500 . ? C13_1 H13_1 0.9500 . ? C14_1 H14_1 0.9500 . ? C15_1 H15_1 0.9500 . ? S1_2 O2_2 1.498(3) . ? S1_2 C16_2 1.787(2) . ? S1_2 C17_2 1.789(2) . ? C16_2 H16A_2 0.9800 . ? C16_2 H16B_2 0.9800 . ? C16_2 H16C_2 0.9800 . ? C17_2 H17A_2 0.9800 . ? C17_2 H17B_2 0.9800 . ? C17_2 H17C_2 0.9800 . ? S1'_2 O2'_2 1.32(6) . ? S1'_2 C17'_2 1.75(3) . ? S1'_2 C16'_2 1.76(3) . ? C16'_2 H16D_2 0.9800 . ? C16'_2 H16E_2 0.9800 . ? C16'_2 H16F_2 0.9800 . ? C17'_2 H17D_2 0.9800 . ? C17'_2 H17E_2 0.9800 . ? C17'_2 H17F_2 0.9800 . ? N1_2 C3_2 1.389(2) . ? N1_2 C10_2 1.433(2) . ? N1_2 C4_2 1.436(2) . ? O1_2 C3_2 1.238(2) . ? C1_2 C4_2 1.398(2) . ? C1_2 C5_2 1.407(2) . ? C1_2 C2_2 1.466(2) . ? N2_2 C3_2 1.346(2) . ? N2_2 H2A_2 0.8800 . ? N2_2 H2B_2 0.8800 . ? C2_2 C13_2 1.340(3) . ? C2_2 H2_2 0.9500 . ? C4_2 C11_2 1.391(2) . ? C5_2 C6_2 1.379(3) . ? C5_2 H5_2 0.9500 . ? C6_2 C9_2 1.392(3) . ? C6_2 H6_2 0.9500 . ? C7_2 C10_2 1.404(2) . ? C7_2 C14_2 1.405(2) . ? C7_2 C13_2 1.466(3) . ? C8_2 C14_2 1.384(3) . ? C8_2 C15_2 1.390(3) . ? C8_2 H8_2 0.9500 . ? C9_2 C11_2 1.387(3) . ? C9_2 H9_2 0.9500 . ? C10_2 C12_2 1.389(3) . ? C11_2 H11_2 0.9500 . ? C12_2 C15_2 1.387(3) . ? C12_2 H12_2 0.9500 . ? C13_2 H13_2 0.9500 . ? C14_2 H14_2 0.9500 . ? C15_2 H15_2 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2_1 S1_1 C16_1 106.54(18) . . ? O2_1 S1_1 C17_1 106.45(16) . . ? C16_1 S1_1 C17_1 97.23(13) . . ? O2'_1 S1'_1 C16'_1 104(3) . . ? O2'_1 S1'_1 C17'_1 109(3) . . ? C16'_1 S1'_1 C17'_1 100.5(15) . . ? S1'_1 C16'_1 H16D_1 109.5 . . ? S1'_1 C16'_1 H16E_1 109.5 . . ? H16D_1 C16'_1 H16E_1 109.5 . . ? S1'_1 C16'_1 H16F_1 109.5 . . ? H16D_1 C16'_1 H16F_1 109.5 . . ? H16E_1 C16'_1 H16F_1 109.5 . . ? S1'_1 C17'_1 H17D_1 109.5 . . ? S1'_1 C17'_1 H17E_1 109.5 . . ? H17D_1 C17'_1 H17E_1 109.5 . . ? S1'_1 C17'_1 H17F_1 109.5 . . ? H17D_1 C17'_1 H17F_1 109.5 . . ? H17E_1 C17'_1 H17F_1 109.5 . . ? C3_1 N1_1 C10_1 118.09(14) . . ? C3_1 N1_1 C4_1 122.22(15) . . ? C10_1 N1_1 C4_1 116.22(13) . . ? C4_1 C1_1 C5_1 117.64(16) . . ? C4_1 C1_1 C2_1 123.00(16) . . ? C5_1 C1_1 C2_1 119.33(16) . . ? C3_1 N2_1 H2A_1 120.0 . . ? C3_1 N2_1 H2B_1 120.0 . . ? H2A_1 N2_1 H2B_1 120.0 . . ? C13_1 C2_1 C1_1 127.02(17) . . ? C13_1 C2_1 H2_1 116.5 . . ? C1_1 C2_1 H2_1 116.5 . . ? O1_1 C3_1 N2_1 123.03(15) . . ? O1_1 C3_1 N1_1 119.69(16) . . ? N2_1 C3_1 N1_1 117.26(15) . . ? C11_1 C4_1 C1_1 120.89(16) . . ? C11_1 C4_1 N1_1 119.52(15) . . ? C1_1 C4_1 N1_1 119.58(15) . . ? C6_1 C5_1 C1_1 121.54(17) . . ? C6_1 C5_1 H5_1 119.2 . . ? C1_1 C5_1 H5_1 119.2 . . ? C5_1 C6_1 C9_1 119.98(17) . . ? C5_1 C6_1 H6_1 120.0 . . ? C9_1 C6_1 H6_1 120.0 . . ? C10_1 C7_1 C14_1 118.22(17) . . ? C10_1 C7_1 C13_1 123.21(16) . . ? C14_1 C7_1 C13_1 118.56(16) . . ? C14_1 C8_1 C15_1 120.45(17) . . ? C14_1 C8_1 H8_1 119.8 . . ? C15_1 C8_1 H8_1 119.8 . . ? C11_1 C9_1 C6_1 119.76(17) . . ? C11_1 C9_1 H9_1 120.1 . . ? C6_1 C9_1 H9_1 120.1 . . ? C12_1 C10_1 C7_1 120.77(16) . . ? C12_1 C10_1 N1_1 119.63(15) . . ? C7_1 C10_1 N1_1 119.59(16) . . ? C9_1 C11_1 C4_1 120.14(17) . . ? C9_1 C11_1 H11_1 119.9 . . ? C4_1 C11_1 H11_1 119.9 . . ? C15_1 C12_1 C10_1 120.10(17) . . ? C15_1 C12_1 H12_1 119.9 . . ? C10_1 C12_1 H12_1 119.9 . . ? C2_1 C13_1 C7_1 127.33(16) . . ? C2_1 C13_1 H13_1 116.3 . . ? C7_1 C13_1 H13_1 116.3 . . ? C8_1 C14_1 C7_1 120.64(17) . . ? C8_1 C14_1 H14_1 119.7 . . ? C7_1 C14_1 H14_1 119.7 . . ? C12_1 C15_1 C8_1 119.76(18) . . ? C12_1 C15_1 H15_1 120.1 . . ? C8_1 C15_1 H15_1 120.1 . . ? O2_2 S1_2 C16_2 106.69(13) . . ? O2_2 S1_2 C17_2 107.11(14) . . ? C16_2 S1_2 C17_2 97.39(11) . . ? O2'_2 S1'_2 C17'_2 114(3) . . ? O2'_2 S1'_2 C16'_2 110(2) . . ? C17'_2 S1'_2 C16'_2 99.3(16) . . ? S1'_2 C16'_2 H16D_2 109.5 . . ? S1'_2 C16'_2 H16E_2 109.5 . . ? H16D_2 C16'_2 H16E_2 109.5 . . ? S1'_2 C16'_2 H16F_2 109.5 . . ? H16D_2 C16'_2 H16F_2 109.5 . . ? H16E_2 C16'_2 H16F_2 109.5 . . ? S1'_2 C17'_2 H17D_2 109.5 . . ? S1'_2 C17'_2 H17E_2 109.5 . . ? H17D_2 C17'_2 H17E_2 109.5 . . ? S1'_2 C17'_2 H17F_2 109.5 . . ? H17D_2 C17'_2 H17F_2 109.5 . . ? H17E_2 C17'_2 H17F_2 109.5 . . ? C3_2 N1_2 C10_2 118.40(14) . . ? C3_2 N1_2 C4_2 122.49(14) . . ? C10_2 N1_2 C4_2 115.86(13) . . ? C4_2 C1_2 C5_2 117.75(16) . . ? C4_2 C1_2 C2_2 123.14(16) . . ? C5_2 C1_2 C2_2 119.04(16) . . ? C3_2 N2_2 H2A_2 120.0 . . ? C3_2 N2_2 H2B_2 120.0 . . ? H2A_2 N2_2 H2B_2 120.0 . . ? C13_2 C2_2 C1_2 126.62(17) . . ? C13_2 C2_2 H2_2 116.7 . . ? C1_2 C2_2 H2_2 116.7 . . ? O1_2 C3_2 N2_2 123.09(15) . . ? O1_2 C3_2 N1_2 119.71(16) . . ? N2_2 C3_2 N1_2 117.17(15) . . ? C11_2 C4_2 C1_2 120.85(16) . . ? C11_2 C4_2 N1_2 119.65(15) . . ? C1_2 C4_2 N1_2 119.50(15) . . ? C6_2 C5_2 C1_2 121.49(17) . . ? C6_2 C5_2 H5_2 119.3 . . ? C1_2 C5_2 H5_2 119.3 . . ? C5_2 C6_2 C9_2 119.81(17) . . ? C5_2 C6_2 H6_2 120.1 . . ? C9_2 C6_2 H6_2 120.1 . . ? C10_2 C7_2 C14_2 118.34(17) . . ? C10_2 C7_2 C13_2 122.95(16) . . ? C14_2 C7_2 C13_2 118.69(16) . . ? C14_2 C8_2 C15_2 120.47(17) . . ? C14_2 C8_2 H8_2 119.8 . . ? C15_2 C8_2 H8_2 119.8 . . ? C11_2 C9_2 C6_2 119.85(17) . . ? C11_2 C9_2 H9_2 120.1 . . ? C6_2 C9_2 H9_2 120.1 . . ? C12_2 C10_2 C7_2 120.69(16) . . ? C12_2 C10_2 N1_2 119.72(15) . . ? C7_2 C10_2 N1_2 119.59(16) . . ? C9_2 C11_2 C4_2 120.21(17) . . ? C9_2 C11_2 H11_2 119.9 . . ? C4_2 C11_2 H11_2 119.9 . . ? C15_2 C12_2 C10_2 120.19(17) . . ? C15_2 C12_2 H12_2 119.9 . . ? C10_2 C12_2 H12_2 119.9 . . ? C2_2 C13_2 C7_2 127.43(16) . . ? C2_2 C13_2 H13_2 116.3 . . ? C7_2 C13_2 H13_2 116.3 . . ? C8_2 C14_2 C7_2 120.54(17) . . ? C8_2 C14_2 H14_2 119.7 . . ? C7_2 C14_2 H14_2 119.7 . . ? C12_2 C15_2 C8_2 119.74(18) . . ? C12_2 C15_2 H15_2 120.1 . . ? C8_2 C15_2 H15_2 120.1 . . ? 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 C4_1 C1_1 C2_1 C13_1 32.4(3) . . . . ? C5_1 C1_1 C2_1 C13_1 -145.69(18) . . . . ? C10_1 N1_1 C3_1 O1_1 -14.8(2) . . . . ? C4_1 N1_1 C3_1 O1_1 -172.99(15) . . . . ? C10_1 N1_1 C3_1 N2_1 166.68(15) . . . . ? C4_1 N1_1 C3_1 N2_1 8.5(2) . . . . ? C5_1 C1_1 C4_1 C11_1 2.8(2) . . . . ? C2_1 C1_1 C4_1 C11_1 -175.36(16) . . . . ? C5_1 C1_1 C4_1 N1_1 -177.18(15) . . . . ? C2_1 C1_1 C4_1 N1_1 4.7(2) . . . . ? C3_1 N1_1 C4_1 C11_1 -88.6(2) . . . . ? C10_1 N1_1 C4_1 C11_1 112.86(18) . . . . ? C3_1 N1_1 C4_1 C1_1 91.38(19) . . . . ? C10_1 N1_1 C4_1 C1_1 -67.2(2) . . . . ? C4_1 C1_1 C5_1 C6_1 -2.1(3) . . . . ? C2_1 C1_1 C5_1 C6_1 176.07(16) . . . . ? C1_1 C5_1 C6_1 C9_1 0.6(3) . . . . ? C5_1 C6_1 C9_1 C11_1 0.4(3) . . . . ? C14_1 C7_1 C10_1 C12_1 -2.9(2) . . . . ? C13_1 C7_1 C10_1 C12_1 175.85(15) . . . . ? C14_1 C7_1 C10_1 N1_1 176.29(14) . . . . ? C13_1 C7_1 C10_1 N1_1 -5.0(2) . . . . ? C3_1 N1_1 C10_1 C12_1 86.6(2) . . . . ? C4_1 N1_1 C10_1 C12_1 -113.88(17) . . . . ? C3_1 N1_1 C10_1 C7_1 -92.55(19) . . . . ? C4_1 N1_1 C10_1 C7_1 66.9(2) . . . . ? C6_1 C9_1 C11_1 C4_1 0.2(3) . . . . ? C1_1 C4_1 C11_1 C9_1 -1.9(3) . . . . ? N1_1 C4_1 C11_1 C9_1 178.09(16) . . . . ? C7_1 C10_1 C12_1 C15_1 2.4(3) . . . . ? N1_1 C10_1 C12_1 C15_1 -176.75(15) . . . . ? C1_1 C2_1 C13_1 C7_1 -1.7(3) . . . . ? C10_1 C7_1 C13_1 C2_1 -30.2(3) . . . . ? C14_1 C7_1 C13_1 C2_1 148.53(18) . . . . ? C15_1 C8_1 C14_1 C7_1 -0.2(3) . . . . ? C10_1 C7_1 C14_1 C8_1 1.8(3) . . . . ? C13_1 C7_1 C14_1 C8_1 -177.04(15) . . . . ? C10_1 C12_1 C15_1 C8_1 -0.8(3) . . . . ? C14_1 C8_1 C15_1 C12_1 -0.4(3) . . . . ? C4_2 C1_2 C2_2 C13_2 -32.9(3) . . . . ? C5_2 C1_2 C2_2 C13_2 144.09(18) . . . . ? C10_2 N1_2 C3_2 O1_2 11.6(2) . . . . ? C4_2 N1_2 C3_2 O1_2 170.35(15) . . . . ? C10_2 N1_2 C3_2 N2_2 -169.97(15) . . . . ? C4_2 N1_2 C3_2 N2_2 -11.2(2) . . . . ? C5_2 C1_2 C4_2 C11_2 -2.5(2) . . . . ? C2_2 C1_2 C4_2 C11_2 174.54(16) . . . . ? C5_2 C1_2 C4_2 N1_2 178.35(15) . . . . ? C2_2 C1_2 C4_2 N1_2 -4.6(2) . . . . ? C3_2 N1_2 C4_2 C11_2 89.2(2) . . . . ? C10_2 N1_2 C4_2 C11_2 -111.52(18) . . . . ? C3_2 N1_2 C4_2 C1_2 -91.63(19) . . . . ? C10_2 N1_2 C4_2 C1_2 67.7(2) . . . . ? C4_2 C1_2 C5_2 C6_2 2.1(3) . . . . ? C2_2 C1_2 C5_2 C6_2 -175.05(16) . . . . ? C1_2 C5_2 C6_2 C9_2 -0.7(3) . . . . ? C5_2 C6_2 C9_2 C11_2 -0.3(3) . . . . ? C14_2 C7_2 C10_2 C12_2 2.6(2) . . . . ? C13_2 C7_2 C10_2 C12_2 -175.80(15) . . . . ? C14_2 C7_2 C10_2 N1_2 -176.91(14) . . . . ? C13_2 C7_2 C10_2 N1_2 4.7(2) . . . . ? C3_2 N1_2 C10_2 C12_2 -86.5(2) . . . . ? C4_2 N1_2 C10_2 C12_2 113.35(17) . . . . ? C3_2 N1_2 C10_2 C7_2 93.03(19) . . . . ? C4_2 N1_2 C10_2 C7_2 -67.1(2) . . . . ? C6_2 C9_2 C11_2 C4_2 -0.1(3) . . . . ? C1_2 C4_2 C11_2 C9_2 1.5(3) . . . . ? N1_2 C4_2 C11_2 C9_2 -179.32(16) . . . . ? C7_2 C10_2 C12_2 C15_2 -1.9(3) . . . . ? N1_2 C10_2 C12_2 C15_2 177.60(15) . . . . ? C1_2 C2_2 C13_2 C7_2 1.8(3) . . . . ? C10_2 C7_2 C13_2 C2_2 30.7(3) . . . . ? C14_2 C7_2 C13_2 C2_2 -147.73(18) . . . . ? C15_2 C8_2 C14_2 C7_2 0.3(3) . . . . ? C10_2 C7_2 C14_2 C8_2 -1.8(2) . . . . ? C13_2 C7_2 C14_2 C8_2 176.68(15) . . . . ? C10_2 C12_2 C15_2 C8_2 0.3(3) . . . . ? C14_2 C8_2 C15_2 C12_2 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.591 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.157 data_ECBZDMSO_180K _database_code_depnum_ccdc_archive 'CCDC 819040' #TrackingRef '- crystal_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O2, C2 H6 O S' _chemical_formula_sum 'C17 H18 N2 O3 S' _chemical_formula_weight 330.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6987(2) _cell_length_b 12.4986(3) _cell_length_c 11.9748(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.0670(10) _cell_angle_gamma 90.00 _cell_volume 1600.98(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9887 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 34.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16256 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 35.00 _reflns_number_total 6997 _reflns_number_gt 5444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.5078P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6997 _refine_ls_number_parameters 222 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1123 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.99620(7) 0.12572(6) 0.74455(7) 0.02060(14) Uani 1 1 d . . . N2 N 1.10540(7) 0.06689(7) 0.90243(7) 0.02447(16) Uani 1 1 d . . . H2A H 1.1096 0.0335 0.9671 0.029 Uiso 1 1 calc R . . H2B H 1.1730 0.0960 0.8746 0.029 Uiso 1 1 calc R . . O1 O 0.89748(6) 0.03420(6) 0.88082(6) 0.02748(15) Uani 1 1 d . . . O2 O 0.95465(7) 0.31901(7) 0.86214(6) 0.03088(17) Uani 1 1 d . . . C1 C 0.99606(8) 0.07345(7) 0.84626(7) 0.01921(15) Uani 1 1 d . . . C2 C 0.87930(8) 0.15031(7) 0.69005(7) 0.01991(15) Uani 1 1 d . . . C3 C 0.81750(9) 0.07119(8) 0.62905(9) 0.02691(19) Uani 1 1 d . . . H3 H 0.8509 0.0008 0.6270 0.032 Uiso 1 1 calc R . . C4 C 0.70701(10) 0.09439(10) 0.57097(10) 0.0325(2) Uani 1 1 d . . . H4 H 0.6643 0.0396 0.5306 0.039 Uiso 1 1 calc R . . C5 C 0.65919(10) 0.19755(10) 0.57208(9) 0.0316(2) Uani 1 1 d . . . H5 H 0.5852 0.2141 0.5305 0.038 Uiso 1 1 calc R . . C6 C 0.71957(9) 0.27630(9) 0.63395(9) 0.02705(19) Uani 1 1 d . . . H6 H 0.6858 0.3466 0.6352 0.032 Uiso 1 1 calc R . . C7 C 0.82956(8) 0.25392(8) 0.69466(8) 0.02110(16) Uani 1 1 d . . . C8 C 0.88778(9) 0.34268(8) 0.75904(8) 0.02466(18) Uani 1 1 d . . . H8 H 0.8365 0.4096 0.7611 0.030 Uiso 1 1 calc R . . C9 C 1.02452(9) 0.36049(8) 0.76926(9) 0.02591(18) Uani 1 1 d . . . H9 H 1.0500 0.4372 0.7768 0.031 Uiso 1 1 calc R . . C10 C 1.11776(8) 0.29085(8) 0.71512(8) 0.02211(16) Uani 1 1 d . . . C11 C 1.22220(9) 0.33997(9) 0.66955(10) 0.0287(2) Uani 1 1 d . . . H11 H 1.2326 0.4151 0.6770 0.034 Uiso 1 1 calc R . . C12 C 1.31124(10) 0.28090(10) 0.61345(10) 0.0331(2) Uani 1 1 d . . . H12 H 1.3814 0.3158 0.5824 0.040 Uiso 1 1 calc R . . C13 C 1.29772(10) 0.17102(10) 0.60278(10) 0.0322(2) Uani 1 1 d . . . H13 H 1.3590 0.1302 0.5653 0.039 Uiso 1 1 calc R . . C14 C 1.19357(9) 0.12086(8) 0.64744(9) 0.02676(19) Uani 1 1 d . . . H14 H 1.1837 0.0457 0.6396 0.032 Uiso 1 1 calc R . . C15 C 1.10407(8) 0.17990(7) 0.70330(7) 0.02011(15) Uani 1 1 d . . . S1 S 0.97317(3) 0.35144(3) 0.44417(2) 0.03074(8) Uani 0.9347(12) 1 d PD A 1 O3 O 0.87227(8) 0.40578(9) 0.37804(10) 0.0487(5) Uani 0.9347(12) 1 d PD A 1 C16 C 1.11653(12) 0.39447(16) 0.38626(16) 0.0392(4) Uani 0.9347(12) 1 d PD A 1 H16A H 1.1318 0.4694 0.4065 0.059 Uiso 0.9347(12) 1 calc PR A 1 H16B H 1.1118 0.3878 0.3047 0.059 Uiso 0.9347(12) 1 calc PR A 1 H16C H 1.1850 0.3500 0.4156 0.059 Uiso 0.9347(12) 1 calc PR A 1 C17 C 0.97758(17) 0.21666(12) 0.39618(15) 0.0515(6) Uani 0.9347(12) 1 d PD A 1 H17A H 0.8991 0.1807 0.4144 0.077 Uiso 0.9347(12) 1 calc PR A 1 H17B H 1.0477 0.1792 0.4326 0.077 Uiso 0.9347(12) 1 calc PR A 1 H17C H 0.9883 0.2159 0.3151 0.077 Uiso 0.9347(12) 1 calc PR A 1 S1' S 0.9761(5) 0.3506(5) 0.3329(5) 0.0450(15) Uani 0.0653(12) 1 d PD A 2 O3' O 0.87227(8) 0.40578(9) 0.37804(10) 0.086(13) Uiso 0.0653(12) 1 d PD A 2 C16' C 1.111(3) 0.395(3) 0.408(4) 0.086(13) Uiso 0.0653(12) 1 d PD A 2 H16D H 1.1072 0.4729 0.4173 0.129 Uiso 0.0653(12) 1 calc PR A 2 H16E H 1.1859 0.3757 0.3673 0.129 Uiso 0.0653(12) 1 calc PR A 2 H16F H 1.1135 0.3609 0.4821 0.129 Uiso 0.0653(12) 1 calc PR A 2 C17' C 0.97758(17) 0.21666(12) 0.39618(15) 0.086(13) Uiso 0.0653(12) 1 d PD A 2 H17D H 1.0268 0.1681 0.3502 0.129 Uiso 0.0653(12) 1 calc PR A 2 H17E H 0.8917 0.1899 0.4007 0.129 Uiso 0.0653(12) 1 calc PR A 2 H17F H 1.0150 0.2206 0.4714 0.129 Uiso 0.0653(12) 1 calc PR A 2 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 N1 0.0157(3) 0.0241(3) 0.0220(3) 0.0076(3) 0.0010(2) 0.0004(2) N2 0.0178(3) 0.0316(4) 0.0239(4) 0.0104(3) -0.0006(3) -0.0009(3) O1 0.0182(3) 0.0362(4) 0.0281(3) 0.0130(3) 0.0013(2) -0.0031(3) O2 0.0288(4) 0.0438(4) 0.0201(3) -0.0042(3) 0.0021(3) 0.0002(3) C1 0.0182(3) 0.0188(3) 0.0207(4) 0.0038(3) 0.0016(3) 0.0016(3) C2 0.0171(3) 0.0237(4) 0.0190(3) 0.0045(3) 0.0010(3) 0.0002(3) C3 0.0245(4) 0.0267(4) 0.0295(5) -0.0002(4) -0.0002(3) -0.0016(3) C4 0.0262(5) 0.0405(6) 0.0307(5) -0.0032(4) -0.0044(4) -0.0055(4) C5 0.0210(4) 0.0456(6) 0.0279(5) 0.0054(4) -0.0053(3) -0.0002(4) C6 0.0209(4) 0.0321(5) 0.0280(4) 0.0071(4) -0.0014(3) 0.0049(3) C7 0.0184(3) 0.0250(4) 0.0199(4) 0.0041(3) 0.0013(3) 0.0018(3) C8 0.0225(4) 0.0259(4) 0.0256(4) -0.0015(3) 0.0019(3) 0.0035(3) C9 0.0251(4) 0.0260(4) 0.0267(4) -0.0034(4) 0.0010(3) -0.0012(3) C10 0.0195(4) 0.0245(4) 0.0224(4) 0.0033(3) 0.0002(3) -0.0014(3) C11 0.0230(4) 0.0278(4) 0.0355(5) 0.0074(4) 0.0025(4) -0.0043(3) C12 0.0228(4) 0.0383(5) 0.0386(6) 0.0108(5) 0.0088(4) -0.0031(4) C13 0.0241(4) 0.0377(5) 0.0350(5) 0.0050(4) 0.0113(4) 0.0035(4) C14 0.0227(4) 0.0277(4) 0.0301(5) 0.0035(4) 0.0063(3) 0.0025(3) C15 0.0167(3) 0.0242(4) 0.0195(4) 0.0063(3) 0.0016(3) 0.0002(3) S1 0.02242(12) 0.04221(17) 0.02778(13) 0.00164(11) 0.00596(9) 0.00226(10) O3 0.0220(4) 0.0531(8) 0.0710(10) 0.0092(6) -0.0009(4) 0.0120(4) C16 0.0222(5) 0.0575(9) 0.0381(7) 0.0023(6) 0.0054(5) -0.0031(5) C17 0.0613(11) 0.0373(8) 0.0560(11) 0.0070(7) 0.0027(8) 0.0021(7) S1' 0.039(3) 0.058(3) 0.038(3) 0.002(2) -0.0003(19) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3821(11) . ? N1 C2 1.4333(11) . ? N1 C15 1.4338(11) . ? N2 C1 1.3410(11) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? O1 C1 1.2412(11) . ? O2 C8 1.4459(12) . ? O2 C9 1.4476(13) . ? C2 C3 1.3895(14) . ? C2 C7 1.4016(13) . ? C3 C4 1.3908(15) . ? C3 H3 0.9500 . ? C4 C5 1.3873(17) . ? C4 H4 0.9500 . ? C5 C6 1.3846(16) . ? C5 H5 0.9500 . ? C6 C7 1.3998(13) . ? C6 H6 0.9500 . ? C7 C8 1.4817(14) . ? C8 C9 1.4825(14) . ? C8 H8 1.0000 . ? C9 C10 1.4822(14) . ? C9 H9 1.0000 . ? C10 C11 1.3950(13) . ? C10 C15 1.4013(13) . ? C11 C12 1.3885(16) . ? C11 H11 0.9500 . ? C12 C13 1.3866(17) . ? C12 H12 0.9500 . ? C13 C14 1.3938(14) . ? C13 H13 0.9500 . ? C14 C15 1.3903(13) . ? C14 H14 0.9500 . ? S1 O3 1.4906(10) . ? S1 C16 1.7782(15) . ? S1 C17 1.7808(16) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? S1' C16' 1.775(18) . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? 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 C1 N1 C2 119.17(7) . . ? C1 N1 C15 122.75(7) . . ? C2 N1 C15 116.29(7) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C8 O2 C9 61.64(6) . . ? O1 C1 N2 123.18(8) . . ? O1 C1 N1 119.71(8) . . ? N2 C1 N1 117.11(8) . . ? C3 C2 C7 120.06(8) . . ? C3 C2 N1 119.30(8) . . ? C7 C2 N1 120.60(8) . . ? C2 C3 C4 120.41(10) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.94(10) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 119.82(9) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 121.01(10) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 118.70(9) . . ? C6 C7 C8 117.51(9) . . ? C2 C7 C8 123.78(8) . . ? O2 C8 C7 119.18(8) . . ? O2 C8 C9 59.24(6) . . ? C7 C8 C9 124.05(8) . . ? O2 C8 H8 114.4 . . ? C7 C8 H8 114.4 . . ? C9 C8 H8 114.4 . . ? O2 C9 C10 119.15(9) . . ? O2 C9 C8 59.12(6) . . ? C10 C9 C8 123.16(9) . . ? O2 C9 H9 114.7 . . ? C10 C9 H9 114.7 . . ? C8 C9 H9 114.7 . . ? C11 C10 C15 118.62(9) . . ? C11 C10 C9 117.59(9) . . ? C15 C10 C9 123.73(8) . . ? C12 C11 C10 121.13(10) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.00(9) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.53(10) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.57(10) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C10 120.15(8) . . ? C14 C15 N1 118.75(8) . . ? C10 C15 N1 121.06(8) . . ? O3 S1 C16 106.05(8) . . ? O3 S1 C17 106.43(8) . . ? C16 S1 C17 97.59(9) . . ? S1 C16 H16A 109.5 . . ? S1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1' C16' H16D 109.5 . . ? S1' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? S1' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 10.96(13) . . . . ? C15 N1 C1 O1 175.14(9) . . . . ? C2 N1 C1 N2 -169.84(8) . . . . ? C15 N1 C1 N2 -5.66(13) . . . . ? C1 N1 C2 C3 -80.94(11) . . . . ? C15 N1 C2 C3 113.88(10) . . . . ? C1 N1 C2 C7 101.31(10) . . . . ? C15 N1 C2 C7 -63.88(11) . . . . ? C7 C2 C3 C4 0.87(15) . . . . ? N1 C2 C3 C4 -176.89(9) . . . . ? C2 C3 C4 C5 1.21(16) . . . . ? C3 C4 C5 C6 -2.05(17) . . . . ? C4 C5 C6 C7 0.82(16) . . . . ? C5 C6 C7 C2 1.24(15) . . . . ? C5 C6 C7 C8 -179.70(9) . . . . ? C3 C2 C7 C6 -2.07(13) . . . . ? N1 C2 C7 C6 175.67(8) . . . . ? C3 C2 C7 C8 178.92(9) . . . . ? N1 C2 C7 C8 -3.34(13) . . . . ? C9 O2 C8 C7 114.45(10) . . . . ? C6 C7 C8 O2 148.02(9) . . . . ? C2 C7 C8 O2 -32.96(13) . . . . ? C6 C7 C8 C9 -141.22(10) . . . . ? C2 C7 C8 C9 37.79(15) . . . . ? C8 O2 C9 C10 -113.34(10) . . . . ? C7 C8 C9 O2 -106.42(11) . . . . ? O2 C8 C9 C10 106.70(11) . . . . ? C7 C8 C9 C10 0.28(16) . . . . ? O2 C9 C10 C11 -148.70(9) . . . . ? C8 C9 C10 C11 141.03(10) . . . . ? O2 C9 C10 C15 34.05(14) . . . . ? C8 C9 C10 C15 -36.22(15) . . . . ? C15 C10 C11 C12 0.03(15) . . . . ? C9 C10 C11 C12 -177.37(10) . . . . ? C10 C11 C12 C13 -0.54(18) . . . . ? C11 C12 C13 C14 0.81(18) . . . . ? C12 C13 C14 C15 -0.59(17) . . . . ? C13 C14 C15 C10 0.08(15) . . . . ? C13 C14 C15 N1 177.85(9) . . . . ? C11 C10 C15 C14 0.20(14) . . . . ? C9 C10 C15 C14 177.42(9) . . . . ? C11 C10 C15 N1 -177.52(9) . . . . ? C9 C10 C15 N1 -0.30(14) . . . . ? C1 N1 C15 C14 84.15(12) . . . . ? C2 N1 C15 C14 -111.24(10) . . . . ? C1 N1 C15 C10 -98.09(11) . . . . ? C2 N1 C15 C10 66.51(12) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.387 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.048