# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Gautam Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad University of Hyderabad Hyderabad Andhra Pradesh 500046 INDIA ; _publ_contact_author_email desiraju@uohyd.ernet.in _publ_contact_author_phone '91 40 23134828' _publ_contact_author_fax '91 40 23010567' _publ_section_title ; Saccharin as a salt former. Enhanced solubilities of saccharinates of active pharmaceutical ingredients. ; _publ_contact_author ; Prof. Gautam R. Desiraju School of Chemistry Univerisity of Hyderabad Hyderabad 500 046 India ; loop_ _publ_author_name 'Prashant M. Bhatt' 'Nittala V. Ravindra' 'Rahul Banerjee' 'Gautam R. Desiraju' data_grd105_m _database_code_depnum_ccdc_archive 'CCDC 253201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Piroxicam and Saccharin molecular complex ; _chemical_name_common 'Piroxicam and Saccharin molecular complex' _chemical_melting_point '176 ' _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 N O3 S' _chemical_formula_sum 'C22 H18 N4 O7 S2' _chemical_formula_weight 514.52 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 9.5117(8) _cell_length_b 10.3862(9) _cell_length_c 12.6635(11) _cell_angle_alpha 66.983(2) _cell_angle_beta 71.011(2) _cell_angle_gamma 89.380(2) _cell_volume 1078.99(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2197 _cell_measurement_theta_min 2.285 _cell_measurement_theta_max 27.772 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart 4k CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7625 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4011 _reflns_number_gt 3208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0581P)^2^+0.2890P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4011 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.36821(6) -0.05874(6) 0.32969(5) 0.01493(16) Uani 1 1 d . . . O4 O 0.28311(18) -0.10034(17) 0.27093(14) 0.0183(4) Uani 1 1 d . . . O6 O 0.27967(18) 0.35552(17) 0.14934(14) 0.0185(4) Uani 1 1 d . . . O7 O 0.63743(18) 0.18999(18) -0.02617(14) 0.0206(4) Uani 1 1 d . . . O5 O 0.43241(18) -0.16423(17) 0.40648(14) 0.0203(4) Uani 1 1 d . . . N3 N 0.5026(2) 0.0658(2) 0.22506(17) 0.0147(4) Uani 1 1 d . . . N4 N 0.4772(2) 0.3561(2) -0.04875(18) 0.0169(5) Uani 1 1 d . . . N2 N 0.6297(2) 0.3666(2) -0.24006(18) 0.0158(4) Uani 1 1 d . . . C22 C 0.3296(3) 0.2443(2) 0.2083(2) 0.0147(5) Uani 1 1 d . . . C13 C 0.5303(3) 0.2407(2) 0.0216(2) 0.0158(5) Uani 1 1 d . . . C18 C 0.2578(3) 0.0308(2) 0.4120(2) 0.0144(5) Uani 1 1 d . . . C19 C 0.2498(2) 0.1734(2) 0.3437(2) 0.0137(5) Uani 1 1 d . . . C11 C 0.6100(3) 0.5259(3) -0.4251(2) 0.0176(5) Uani 1 1 d . . . C15 C 0.0830(3) 0.1801(3) 0.5313(2) 0.0192(5) Uani 1 1 d . . . C17 C 0.1799(3) -0.0365(3) 0.5368(2) 0.0177(5) Uani 1 1 d . . . C8 C 0.5203(3) 0.4160(2) -0.1731(2) 0.0141(5) Uani 1 1 d . . . C21 C 0.4493(3) 0.1882(2) 0.1520(2) 0.0148(5) Uani 1 1 d . . . C12 C 0.6747(3) 0.4199(3) -0.3638(2) 0.0174(5) Uani 1 1 d . . . C14 C 0.1612(3) 0.2463(3) 0.4060(2) 0.0162(5) Uani 1 1 d . . . C10 C 0.4955(3) 0.5802(3) -0.3587(2) 0.0170(5) Uani 1 1 d . . . C16 C 0.0915(3) 0.0398(3) 0.5959(2) 0.0207(5) Uani 1 1 d . . . C20 C 0.6248(3) 0.0960(3) 0.2636(3) 0.0221(6) Uani 1 1 d . . . C9 C 0.4505(3) 0.5255(2) -0.2337(2) 0.0173(5) Uani 1 1 d . . . S2 S 0.95126(7) 0.55527(6) 0.26469(5) 0.01723(16) Uani 1 1 d . . . O1 O 1.15871(19) 0.59876(18) -0.05475(15) 0.0227(4) Uani 1 1 d . . . O3 O 1.0293(2) 0.6079(2) 0.32168(16) 0.0279(4) Uani 1 1 d . . . O2 O 0.83726(19) 0.43688(18) 0.34433(15) 0.0254(4) Uani 1 1 d . . . C5 C 0.8878(3) 0.6922(2) 0.1630(2) 0.0171(5) Uani 1 1 d . . . N1 N 1.0708(2) 0.5223(2) 0.15406(18) 0.0188(5) Uani 1 1 d . . . C7 C 1.0750(3) 0.6073(2) 0.0378(2) 0.0183(5) Uani 1 1 d . . . C4 C 0.7806(3) 0.7769(3) 0.1892(2) 0.0215(6) Uani 1 1 d . . . C6 C 0.9634(3) 0.7072(2) 0.0444(2) 0.0175(5) Uani 1 1 d . . . C1 C 0.9328(3) 0.8078(3) -0.0523(2) 0.0232(6) Uani 1 1 d . . . C2 C 0.8265(3) 0.8946(3) -0.0280(2) 0.0249(6) Uani 1 1 d . . . C3 C 0.7517(3) 0.8800(3) 0.0916(3) 0.0247(6) Uani 1 1 d . . . H6 H 0.757(3) 0.376(2) -0.402(2) 0.013(6) Uiso 1 1 d . . . H9 H 0.375(3) 0.554(3) -0.186(2) 0.018(7) Uiso 1 1 d . . . H14 H 0.702(3) 0.164(3) 0.187(2) 0.018(6) Uiso 1 1 d . . . H13 H 0.667(3) 0.009(3) 0.301(2) 0.030(7) Uiso 1 1 d . . . H8 H 0.448(3) 0.651(3) -0.401(2) 0.016(6) Uiso 1 1 d . . . H7 H 0.642(3) 0.564(3) -0.515(2) 0.020(7) Uiso 1 1 d . . . H10 H 0.666(3) 0.298(3) -0.196(2) 0.019(7) Uiso 1 1 d . . . H4 H 0.676(3) 0.942(3) 0.104(2) 0.020(7) Uiso 1 1 d . . . H1 H 1.130(3) 0.463(3) 0.164(3) 0.028(8) Uiso 1 1 d . . . H12 H 0.592(3) 0.138(3) 0.320(3) 0.034(8) Uiso 1 1 d . . . H3 H 0.809(3) 0.961(3) -0.092(3) 0.029(8) Uiso 1 1 d . . . H5 H 0.737(3) 0.768(3) 0.269(3) 0.027(7) Uiso 1 1 d . . . H11 H 0.411(4) 0.381(3) -0.012(3) 0.038(10) Uiso 1 1 d . . . H2 H 0.980(3) 0.811(3) -0.130(3) 0.030(8) Uiso 1 1 d . . . H15 H 0.155(3) 0.342(3) 0.362(2) 0.016(6) Uiso 1 1 d . . . H18 H 0.188(3) -0.129(3) 0.578(2) 0.019(7) Uiso 1 1 d . . . H16 H 0.026(3) 0.228(3) 0.575(2) 0.027(7) Uiso 1 1 d . . . H17 H 0.037(3) -0.011(3) 0.686(2) 0.020(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0173(3) 0.0131(3) 0.0137(3) -0.0045(2) -0.0059(2) 0.0040(2) O4 0.0219(9) 0.0171(9) 0.0180(8) -0.0083(7) -0.0081(7) 0.0038(7) O6 0.0207(9) 0.0162(9) 0.0148(8) -0.0036(7) -0.0050(7) 0.0085(7) O7 0.0207(9) 0.0219(10) 0.0165(8) -0.0065(7) -0.0052(7) 0.0108(7) O5 0.0227(9) 0.0175(9) 0.0184(9) -0.0039(7) -0.0085(7) 0.0060(7) N3 0.0145(10) 0.0144(10) 0.0147(10) -0.0046(8) -0.0063(8) 0.0054(8) N4 0.0164(11) 0.0188(11) 0.0126(10) -0.0062(9) -0.0018(9) 0.0072(9) N2 0.0169(11) 0.0158(11) 0.0145(10) -0.0056(9) -0.0061(9) 0.0048(8) C22 0.0162(12) 0.0134(12) 0.0153(12) -0.0056(10) -0.0067(10) 0.0011(9) C13 0.0150(12) 0.0148(12) 0.0174(12) -0.0058(10) -0.0064(10) 0.0040(9) C18 0.0127(12) 0.0185(13) 0.0136(11) -0.0070(10) -0.0059(9) 0.0020(9) C19 0.0120(11) 0.0169(12) 0.0131(11) -0.0058(10) -0.0058(9) 0.0006(9) C11 0.0209(13) 0.0185(13) 0.0128(12) -0.0064(10) -0.0050(10) -0.0011(10) C15 0.0168(13) 0.0267(14) 0.0177(12) -0.0129(11) -0.0060(10) 0.0053(10) C17 0.0182(13) 0.0173(14) 0.0165(12) -0.0039(11) -0.0084(10) 0.0016(10) C8 0.0131(12) 0.0141(12) 0.0136(11) -0.0056(10) -0.0028(10) -0.0006(9) C21 0.0162(12) 0.0135(12) 0.0132(11) -0.0034(10) -0.0059(10) 0.0034(9) C12 0.0179(13) 0.0175(13) 0.0156(12) -0.0080(10) -0.0029(10) 0.0002(10) C14 0.0145(12) 0.0161(13) 0.0186(12) -0.0071(11) -0.0064(10) 0.0015(10) C10 0.0166(13) 0.0157(13) 0.0169(12) -0.0038(10) -0.0072(10) 0.0019(10) C16 0.0188(13) 0.0282(15) 0.0112(12) -0.0050(11) -0.0040(10) 0.0008(10) C20 0.0197(14) 0.0202(14) 0.0260(14) -0.0056(12) -0.0122(12) 0.0036(11) C9 0.0160(13) 0.0152(13) 0.0185(12) -0.0061(10) -0.0043(11) 0.0009(10) S2 0.0171(3) 0.0206(3) 0.0144(3) -0.0080(3) -0.0052(2) 0.0084(2) O1 0.0235(10) 0.0242(10) 0.0157(9) -0.0089(8) -0.0001(8) 0.0059(7) O3 0.0305(10) 0.0359(11) 0.0285(10) -0.0197(9) -0.0165(9) 0.0132(8) O2 0.0213(9) 0.0241(10) 0.0207(9) -0.0012(8) -0.0046(8) 0.0065(8) C5 0.0166(12) 0.0151(12) 0.0188(12) -0.0055(10) -0.0068(10) 0.0047(9) N1 0.0184(11) 0.0193(12) 0.0173(11) -0.0077(9) -0.0048(9) 0.0109(9) C7 0.0185(13) 0.0140(12) 0.0186(13) -0.0046(10) -0.0043(11) -0.0007(10) C4 0.0234(14) 0.0220(14) 0.0207(13) -0.0115(11) -0.0064(11) 0.0090(11) C6 0.0178(12) 0.0147(12) 0.0176(12) -0.0058(10) -0.0040(10) 0.0017(10) C1 0.0254(14) 0.0236(14) 0.0194(13) -0.0074(11) -0.0081(12) 0.0048(11) C2 0.0268(15) 0.0211(14) 0.0263(14) -0.0048(12) -0.0145(12) 0.0076(11) C3 0.0244(14) 0.0213(14) 0.0310(15) -0.0116(12) -0.0121(12) 0.0102(11) _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 1.4306(16) . ? S1 O5 1.4345(17) . ? S1 N3 1.6297(19) . ? S1 C18 1.755(2) . ? O6 C22 1.289(3) . ? O7 C13 1.232(3) . ? N3 C21 1.448(3) . ? N3 C20 1.478(3) . ? N4 C8 1.362(3) . ? N4 C13 1.389(3) . ? N4 H11 0.76(3) . ? N2 C8 1.349(3) . ? N2 C12 1.355(3) . ? N2 H10 0.87(3) . ? C22 C21 1.388(3) . ? C22 C19 1.495(3) . ? C13 C21 1.448(3) . ? C18 C17 1.386(3) . ? C18 C19 1.409(3) . ? C19 C14 1.388(3) . ? C11 C12 1.349(4) . ? C11 C10 1.405(3) . ? C11 H7 0.98(2) . ? C15 C16 1.381(4) . ? C15 C14 1.391(3) . ? C15 H16 0.93(3) . ? C17 C16 1.391(4) . ? C17 H18 0.91(3) . ? C8 C9 1.398(3) . ? C12 H6 0.98(3) . ? C14 H15 0.94(3) . ? C10 C9 1.368(3) . ? C10 H8 0.94(3) . ? C16 H17 1.00(3) . ? C20 H14 1.00(3) . ? C20 H13 0.99(3) . ? C20 H12 0.94(3) . ? C9 H9 0.90(3) . ? S2 O3 1.4271(17) . ? S2 O2 1.4326(18) . ? S2 N1 1.644(2) . ? S2 C5 1.761(2) . ? O1 C7 1.219(3) . ? C5 C4 1.383(3) . ? C5 C6 1.384(3) . ? N1 C7 1.377(3) . ? N1 H1 0.83(3) . ? C7 C6 1.482(3) . ? C4 C3 1.389(4) . ? C4 H5 0.93(3) . ? C6 C1 1.378(3) . ? C1 C2 1.387(4) . ? C1 H2 0.93(3) . ? C2 C3 1.394(4) . ? C2 H3 0.90(3) . ? C3 H4 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O5 118.75(10) . . ? O4 S1 N3 108.45(10) . . ? O5 S1 N3 108.24(10) . . ? O4 S1 C18 108.55(10) . . ? O5 S1 C18 109.64(10) . . ? N3 S1 C18 101.89(10) . . ? C21 N3 C20 115.69(19) . . ? C21 N3 S1 113.49(15) . . ? C20 N3 S1 115.88(16) . . ? C8 N4 C13 126.6(2) . . ? C8 N4 H11 118(2) . . ? C13 N4 H11 114(2) . . ? C8 N2 C12 122.3(2) . . ? C8 N2 H10 112.8(17) . . ? C12 N2 H10 124.9(17) . . ? O6 C22 C21 123.3(2) . . ? O6 C22 C19 116.7(2) . . ? C21 C22 C19 119.9(2) . . ? O7 C13 N4 121.2(2) . . ? O7 C13 C21 124.5(2) . . ? N4 C13 C21 114.3(2) . . ? C17 C18 C19 122.0(2) . . ? C17 C18 S1 121.58(19) . . ? C19 C18 S1 116.34(17) . . ? C14 C19 C18 117.7(2) . . ? C14 C19 C22 120.4(2) . . ? C18 C19 C22 121.9(2) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H7 120.8(15) . . ? C10 C11 H7 120.2(15) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H16 117.6(17) . . ? C14 C15 H16 122.0(17) . . ? C18 C17 C16 118.6(2) . . ? C18 C17 H18 119.4(16) . . ? C16 C17 H18 122.0(16) . . ? N2 C8 N4 119.7(2) . . ? N2 C8 C9 118.8(2) . . ? N4 C8 C9 121.5(2) . . ? C22 C21 N3 120.09(19) . . ? C22 C21 C13 125.7(2) . . ? N3 C21 C13 114.2(2) . . ? C11 C12 N2 120.5(2) . . ? C11 C12 H6 125.3(14) . . ? N2 C12 H6 114.2(14) . . ? C19 C14 C15 120.8(2) . . ? C19 C14 H15 118.7(15) . . ? C15 C14 H15 120.5(15) . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H8 120.9(15) . . ? C11 C10 H8 118.9(15) . . ? C15 C16 C17 120.5(2) . . ? C15 C16 H17 122.6(15) . . ? C17 C16 H17 116.9(15) . . ? N3 C20 H14 105.0(13) . . ? N3 C20 H13 111.1(15) . . ? H14 C20 H13 111(2) . . ? N3 C20 H12 111.5(17) . . ? H14 C20 H12 109(2) . . ? H13 C20 H12 109(2) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 H9 123.8(16) . . ? C8 C9 H9 116.8(16) . . ? O3 S2 O2 116.37(11) . . ? O3 S2 N1 110.39(11) . . ? O2 S2 N1 110.65(11) . . ? O3 S2 C5 111.41(11) . . ? O2 S2 C5 112.51(11) . . ? N1 S2 C5 93.13(11) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 S2 128.7(2) . . ? C6 C5 S2 109.46(18) . . ? C7 N1 S2 115.31(18) . . ? C7 N1 H1 120(2) . . ? S2 N1 H1 125(2) . . ? O1 C7 N1 123.9(2) . . ? O1 C7 C6 126.6(2) . . ? N1 C7 C6 109.5(2) . . ? C5 C4 C3 117.7(2) . . ? C5 C4 H5 119.7(17) . . ? C3 C4 H5 122.4(17) . . ? C1 C6 C5 120.5(2) . . ? C1 C6 C7 126.9(2) . . ? C5 C6 C7 112.6(2) . . ? C6 C1 C2 118.5(2) . . ? C6 C1 H2 118.6(18) . . ? C2 C1 H2 122.8(18) . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H3 117.9(18) . . ? C3 C2 H3 121.3(18) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H4 121.7(15) . . ? C2 C3 H4 117.6(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.438 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.066 data_grd120_a _database_code_depnum_ccdc_archive 'CCDC 253202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Mirtazapine and Saccharin molecular complex water structure ; _chemical_name_common 'Mirtazapine and Saccharin molecular complex water structure' _chemical_melting_point '189 ' _chemical_formula_moiety 'C17 H20 N3, C7 H4 N O3 S, H2 O, H2 O0.34' _chemical_formula_sum 'C24 H28 N4 O4.34 S' _chemical_formula_weight 473.84 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)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5791(12) _cell_length_b 26.733(3) _cell_length_c 9.4055(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.511(2) _cell_angle_gamma 90.00 _cell_volume 2270.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5188 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.02 _exptl_crystal_description Prismic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart 4k CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12697 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4002 _reflns_number_gt 3485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0557P)^2^+0.9018P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4002 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.007 _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 S1 S 0.86152(5) 0.039527(16) 0.65105(5) 0.02640(14) Uani 1 1 d . . . O2 O 0.98142(14) 0.06563(5) 0.62332(16) 0.0353(3) Uani 1 1 d . . . O3 O 0.90178(14) -0.00650(5) 0.73289(15) 0.0349(3) Uani 1 1 d . . . O1 O 0.54685(16) 0.11330(5) 0.67141(19) 0.0459(4) Uani 1 1 d . . . N4 N 0.77501(17) 0.07622(6) 0.72943(18) 0.0313(4) Uani 1 1 d . . . C2 C 0.71239(19) 0.03052(7) 0.4813(2) 0.0277(4) Uani 1 1 d . . . C7 C 0.6335(2) 0.08538(7) 0.6385(2) 0.0336(5) Uani 1 1 d . . . C1 C 0.5944(2) 0.05775(7) 0.4920(2) 0.0304(4) Uani 1 1 d . . . C3 C 0.7046(2) 0.00174(8) 0.3572(2) 0.0361(5) Uani 1 1 d . . . H3 H 0.7873 -0.0169 0.3523 0.043 Uiso 1 1 calc R . . C5 C 0.4500(2) 0.02820(9) 0.2480(2) 0.0451(6) Uani 1 1 d . . . H5 H 0.3593 0.0272 0.1661 0.054 Uiso 1 1 calc R . . C6 C 0.4600(2) 0.05662(8) 0.3740(3) 0.0418(6) Uani 1 1 d . . . H6 H 0.3771 0.0749 0.3797 0.050 Uiso 1 1 calc R . . C4 C 0.5701(2) 0.00129(9) 0.2398(2) 0.0453(6) Uani 1 1 d . . . H4 H 0.5605 -0.0179 0.1520 0.054 Uiso 1 1 calc R . . N3 N 1.24751(15) 0.21888(6) 0.90655(16) 0.0262(3) Uani 1 1 d . . . N2 N 1.05383(15) 0.19514(5) 0.99513(16) 0.0243(3) Uani 1 1 d . . . N1 N 0.87360(16) 0.11239(5) 1.01939(19) 0.0262(3) Uani 1 1 d . . . H36 H 0.849(2) 0.0993(8) 0.920(3) 0.044(6) Uiso 1 1 d . . . C19 C 1.14397(17) 0.23263(7) 0.96524(18) 0.0230(4) Uani 1 1 d . . . C20 C 0.89280(18) 0.19528(6) 0.91154(19) 0.0216(4) Uani 1 1 d . . . H20 H 0.8770 0.1769 0.8148 0.026 Uiso 1 1 calc R . . C9 C 0.64127(19) 0.33146(7) 0.7905(2) 0.0272(4) Uani 1 1 d . . . H9 H 0.5821 0.3608 0.7641 0.033 Uiso 1 1 calc R . . C21 C 0.81781(19) 0.16492(6) 1.0035(2) 0.0247(4) Uani 1 1 d . . . H21A H 0.8394 0.1801 1.1045 0.030 Uiso 1 1 calc R . . H21B H 0.7092 0.1652 0.9523 0.030 Uiso 1 1 calc R . . C16 C 1.2233(2) 0.31751(7) 0.9886(2) 0.0309(4) Uani 1 1 d . . . H16 H 1.2166 0.3512 1.0179 0.037 Uiso 1 1 calc R . . C11 C 0.68150(18) 0.24511(7) 0.74991(19) 0.0237(4) Uani 1 1 d . . . H11 H 0.6496 0.2152 0.6937 0.028 Uiso 1 1 calc R . . C8 C 0.7731(2) 0.33228(7) 0.9097(2) 0.0260(4) Uani 1 1 d . . . H8 H 0.8048 0.3625 0.9640 0.031 Uiso 1 1 calc R . . C13 C 0.86016(19) 0.28963(6) 0.95180(19) 0.0225(4) Uani 1 1 d . . . C12 C 0.81406(18) 0.24528(6) 0.87165(19) 0.0210(4) Uani 1 1 d . . . C18 C 1.33660(19) 0.25501(7) 0.8859(2) 0.0306(4) Uani 1 1 d . . . H18 H 1.4091 0.2460 0.8421 0.037 Uiso 1 1 calc R . . C15 C 1.12809(19) 0.28180(7) 1.00979(19) 0.0249(4) Uani 1 1 d . . . C23 C 1.11017(19) 0.14393(7) 1.0025(2) 0.0294(4) Uani 1 1 d . . . H23A H 1.2190 0.1438 1.0526 0.035 Uiso 1 1 calc R . . H23B H 1.0880 0.1305 0.8992 0.035 Uiso 1 1 calc R . . C24 C 0.7998(2) 0.08024(7) 1.1030(2) 0.0345(5) Uani 1 1 d . . . H24A H 0.8288 0.0913 1.2082 0.052 Uiso 1 1 calc R . . H24B H 0.8299 0.0454 1.0996 0.052 Uiso 1 1 calc R . . H24C H 0.6920 0.0829 1.0561 0.052 Uiso 1 1 calc R . . C10 C 0.59613(19) 0.28790(7) 0.7102(2) 0.0264(4) Uani 1 1 d . . . H10 H 0.5061 0.2872 0.6274 0.032 Uiso 1 1 calc R . . C14 C 1.00899(19) 0.29272(7) 1.0753(2) 0.0272(4) Uani 1 1 d . . . H14A H 1.0233 0.3266 1.1205 0.033 Uiso 1 1 calc R . . H14B H 1.0135 0.2682 1.1556 0.033 Uiso 1 1 calc R . . C22 C 1.0379(2) 0.11143(7) 1.0902(2) 0.0310(4) Uani 1 1 d . . . H22A H 1.0739 0.0766 1.0928 0.037 Uiso 1 1 calc R . . H22B H 1.0659 0.1237 1.1954 0.037 Uiso 1 1 calc R . . C17 C 1.3288(2) 0.30416(8) 0.9244(2) 0.0344(5) Uani 1 1 d . . . H17 H 1.3940 0.3284 0.9075 0.041 Uiso 1 1 calc R . . O4 O 0.42171(19) 0.12624(6) 0.9014(2) 0.0493(4) Uani 1 1 d . . . H34 H 0.364(3) 0.1501(11) 0.886(3) 0.074 Uiso 1 1 d . . . H35 H 0.453(3) 0.1239(11) 0.822(3) 0.074 Uiso 1 1 d . . . O11 O 0.2372(4) 0.04741(14) 0.9213(4) 0.0288(14) Uani 0.330(5) 1 d P . . H51 H 0.1682 0.0502 0.8260 0.043 Uiso 0.330(5) 1 d PR . . H52 H 0.3027 0.0715 0.8970 0.043 Uiso 0.330(5) 1 d PR . . 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 0.0219(2) 0.0216(2) 0.0334(3) 0.00338(18) 0.00617(19) 0.00205(17) O2 0.0230(7) 0.0334(8) 0.0475(8) 0.0014(6) 0.0092(6) -0.0022(6) O3 0.0351(8) 0.0276(7) 0.0380(8) 0.0080(6) 0.0067(6) 0.0089(6) O1 0.0353(8) 0.0270(8) 0.0816(11) 0.0037(7) 0.0277(8) 0.0082(6) N4 0.0284(8) 0.0223(8) 0.0420(10) 0.0005(7) 0.0104(7) 0.0021(6) C2 0.0224(9) 0.0253(10) 0.0321(10) 0.0103(8) 0.0047(8) -0.0051(7) C7 0.0268(10) 0.0183(9) 0.0562(13) 0.0091(9) 0.0147(9) -0.0001(8) C1 0.0244(9) 0.0198(9) 0.0442(11) 0.0113(8) 0.0080(8) -0.0035(7) C3 0.0319(10) 0.0416(12) 0.0357(11) 0.0059(9) 0.0125(9) -0.0086(9) C5 0.0338(12) 0.0478(13) 0.0407(12) 0.0172(11) -0.0047(9) -0.0194(10) C6 0.0209(10) 0.0303(11) 0.0665(15) 0.0240(11) 0.0043(9) -0.0045(8) C4 0.0413(12) 0.0560(14) 0.0359(11) 0.0075(10) 0.0095(9) -0.0199(11) N3 0.0185(7) 0.0318(9) 0.0268(8) 0.0064(7) 0.0053(6) -0.0002(6) N2 0.0189(7) 0.0229(8) 0.0306(8) 0.0069(6) 0.0075(6) 0.0013(6) N1 0.0264(8) 0.0196(8) 0.0362(9) 0.0055(7) 0.0153(7) 0.0021(6) C19 0.0165(8) 0.0287(10) 0.0201(8) 0.0065(7) 0.0012(7) -0.0014(7) C20 0.0193(8) 0.0201(9) 0.0258(9) 0.0012(7) 0.0081(7) -0.0003(7) C9 0.0268(9) 0.0233(9) 0.0354(10) 0.0045(8) 0.0156(8) 0.0068(7) C21 0.0232(9) 0.0194(9) 0.0334(10) 0.0037(7) 0.0117(7) 0.0023(7) C16 0.0276(10) 0.0286(10) 0.0302(10) 0.0013(8) 0.0012(8) -0.0062(8) C11 0.0206(8) 0.0214(9) 0.0292(9) -0.0011(7) 0.0084(7) -0.0028(7) C8 0.0327(10) 0.0204(9) 0.0294(10) -0.0027(7) 0.0162(8) -0.0014(7) C13 0.0249(9) 0.0239(9) 0.0209(9) 0.0004(7) 0.0107(7) -0.0019(7) C12 0.0201(8) 0.0212(9) 0.0243(9) 0.0028(7) 0.0107(7) -0.0001(7) C18 0.0187(9) 0.0393(11) 0.0323(10) 0.0096(9) 0.0067(7) -0.0026(8) C15 0.0226(9) 0.0286(10) 0.0192(9) 0.0007(7) 0.0011(7) -0.0026(7) C23 0.0218(9) 0.0268(10) 0.0404(11) 0.0100(8) 0.0117(8) 0.0049(7) C24 0.0381(11) 0.0212(10) 0.0521(12) 0.0099(9) 0.0255(10) 0.0017(8) C10 0.0189(8) 0.0291(10) 0.0309(10) 0.0028(8) 0.0079(7) 0.0007(7) C14 0.0309(10) 0.0273(10) 0.0217(9) -0.0029(7) 0.0066(8) -0.0029(8) C22 0.0275(10) 0.0264(10) 0.0398(11) 0.0112(8) 0.0123(8) 0.0070(8) C17 0.0243(10) 0.0362(11) 0.0396(11) 0.0075(9) 0.0068(8) -0.0093(8) O4 0.0475(10) 0.0439(10) 0.0585(10) -0.0033(8) 0.0203(8) 0.0067(7) O11 0.029(2) 0.028(2) 0.027(2) -0.0014(16) 0.0045(16) 0.0049(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4342(13) . ? S1 O2 1.4403(14) . ? S1 N4 1.6126(16) . ? S1 C2 1.7674(18) . ? O1 C7 1.230(2) . ? N4 C7 1.362(2) . ? C2 C1 1.376(3) . ? C2 C3 1.379(3) . ? C7 C1 1.496(3) . ? C1 C6 1.391(3) . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C5 C6 1.383(3) . ? C5 C4 1.381(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? N3 C19 1.338(2) . ? N3 C18 1.345(2) . ? N2 C19 1.411(2) . ? N2 C23 1.464(2) . ? N2 C20 1.479(2) . ? N1 C22 1.491(2) . ? N1 C21 1.492(2) . ? N1 C24 1.493(2) . ? N1 H36 0.95(2) . ? C19 C15 1.403(3) . ? C20 C12 1.519(2) . ? C20 C21 1.529(2) . ? C20 H20 1.0000 . ? C9 C10 1.377(3) . ? C9 C8 1.381(3) . ? C9 H9 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C16 C15 1.380(3) . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C11 C10 1.383(2) . ? C11 C12 1.397(2) . ? C11 H11 0.9500 . ? C8 C13 1.390(2) . ? C8 H8 0.9500 . ? C13 C12 1.395(2) . ? C13 C14 1.511(2) . ? C18 C17 1.371(3) . ? C18 H18 0.9500 . ? C15 C14 1.496(2) . ? C23 C22 1.515(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C10 H10 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C17 H17 0.9500 . ? O4 H34 0.83(3) . ? O4 H35 0.90(3) . ? O11 H51 0.9219 . ? O11 H52 0.9781 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O2 115.16(8) . . ? O3 S1 N4 111.32(8) . . ? O2 S1 N4 110.53(8) . . ? O3 S1 C2 111.05(8) . . ? O2 S1 C2 110.81(8) . . ? N4 S1 C2 96.43(9) . . ? C7 N4 S1 112.21(14) . . ? C1 C2 C3 122.93(18) . . ? C1 C2 S1 107.32(15) . . ? C3 C2 S1 129.74(15) . . ? O1 C7 N4 124.4(2) . . ? O1 C7 C1 123.29(18) . . ? N4 C7 C1 112.32(16) . . ? C2 C1 C6 119.6(2) . . ? C2 C1 C7 111.68(16) . . ? C6 C1 C7 128.74(19) . . ? C2 C3 C4 116.8(2) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? C6 C5 C4 120.90(19) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.5(2) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C19 N3 C18 117.12(16) . . ? C19 N2 C23 115.65(14) . . ? C19 N2 C20 119.41(13) . . ? C23 N2 C20 109.27(13) . . ? C22 N1 C21 110.51(14) . . ? C22 N1 C24 111.73(15) . . ? C21 N1 C24 112.19(14) . . ? C22 N1 H36 108.1(13) . . ? C21 N1 H36 106.5(13) . . ? C24 N1 H36 107.6(14) . . ? N3 C19 C15 123.36(16) . . ? N3 C19 N2 118.32(16) . . ? C15 C19 N2 118.12(15) . . ? N2 C20 C12 118.51(14) . . ? N2 C20 C21 107.55(13) . . ? C12 C20 C21 108.57(13) . . ? N2 C20 H20 107.2 . . ? C12 C20 H20 107.2 . . ? C21 C20 H20 107.2 . . ? C10 C9 C8 119.56(16) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N1 C21 C20 109.64(14) . . ? N1 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? N1 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C15 C16 C17 119.88(18) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C10 C11 C12 120.81(16) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C9 C8 C13 121.15(17) . . ? C9 C8 H8 119.4 . . ? C13 C8 H8 119.4 . . ? C8 C13 C12 119.46(16) . . ? C8 C13 C14 119.77(15) . . ? C12 C13 C14 120.60(15) . . ? C13 C12 C11 118.85(15) . . ? C13 C12 C20 124.95(15) . . ? C11 C12 C20 116.11(15) . . ? N3 C18 C17 123.81(18) . . ? N3 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? C16 C15 C19 117.51(17) . . ? C16 C15 C14 123.83(17) . . ? C19 C15 C14 118.66(15) . . ? N2 C23 C22 109.49(14) . . ? N2 C23 H23A 109.8 . . ? C22 C23 H23A 109.8 . . ? N2 C23 H23B 109.8 . . ? C22 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? N1 C24 H24A 109.5 . . ? N1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 C10 C11 120.16(16) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C15 C14 C13 109.03(14) . . ? C15 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? N1 C22 C23 110.68(14) . . ? N1 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C18 C17 C16 118.28(17) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? H34 O4 H35 107(3) . . ? H51 O11 H52 91.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.347 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.045 data_grd126_m _database_code_depnum_ccdc_archive 'CCDC 253203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Haloperidol and Saccharin molecular complex ; _chemical_name_common 'Haloperidol and Saccharin molecular complex' _chemical_melting_point '198 ' _chemical_formula_moiety 'C21 H24 Cl F N O2, C7 H4 N O3 S ' _chemical_formula_sum 'C28 H28 Cl F N2 O5 S' _chemical_formula_weight 559.03 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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 19.0609(10) _cell_length_b 7.2197(4) _cell_length_c 21.5624(12) _cell_angle_alpha 90.00 _cell_angle_beta 113.961(2) _cell_angle_gamma 90.00 _cell_volume 2711.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2768 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.79 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11182 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 24.71 _reflns_number_total 4610 _reflns_number_gt 3746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0671P)^2^+0.3380P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4610 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.75054(4) 0.29744(9) 0.07608(3) 0.02043(18) Uani 1 1 d . . . Cl1 Cl 0.16718(4) 1.27618(12) 0.15460(4) 0.0434(2) Uani 1 1 d . . . F1 F 1.14185(9) 0.7691(2) 0.17315(8) 0.0359(4) Uani 1 1 d . . . O4 O 0.42205(10) 1.0428(2) 0.02732(8) 0.0213(4) Uani 1 1 d . . . O1 O 0.92702(10) 0.3338(2) 0.22976(8) 0.0229(4) Uani 1 1 d . . . O5 O 0.88586(9) 0.9554(2) 0.27596(8) 0.0230(4) Uani 1 1 d . . . C13 C 0.36396(13) 1.0599(3) 0.10888(11) 0.0186(5) Uani 1 1 d . . . O2 O 0.71092(11) 0.4621(3) 0.04240(9) 0.0328(5) Uani 1 1 d . . . O3 O 0.70240(10) 0.1352(3) 0.06525(8) 0.0271(4) Uani 1 1 d . . . N2 N 0.59017(11) 0.8413(3) 0.14746(10) 0.0172(5) Uani 1 1 d . . . C19 C 1.07707(15) 0.7984(4) 0.18349(13) 0.0265(6) Uani 1 1 d . . . C24 C 0.57608(15) 1.0451(3) 0.13362(13) 0.0191(5) Uani 1 1 d . . . C2 C 0.89410(15) 0.2659(3) 0.11175(12) 0.0198(6) Uani 1 1 d . . . C21 C 0.80212(14) 0.8046(4) 0.17516(13) 0.0202(6) Uani 1 1 d . . . N1 N 0.80020(12) 0.3298(3) 0.15589(10) 0.0205(5) Uani 1 1 d . . . C20 C 0.87833(14) 0.8786(3) 0.22321(12) 0.0187(5) Uani 1 1 d . . . C22 C 0.73511(14) 0.8631(4) 0.19230(13) 0.0201(6) Uani 1 1 d . . . C28 C 0.52216(15) 0.7353(4) 0.09939(13) 0.0189(5) Uani 1 1 d . . . C27 C 0.44943(15) 0.7897(4) 0.10706(13) 0.0201(6) Uani 1 1 d . . . C16 C 0.94664(14) 0.8517(3) 0.20616(12) 0.0183(5) Uani 1 1 d . . . C14 C 1.08215(16) 0.9019(4) 0.23871(13) 0.0248(6) Uani 1 1 d . . . C15 C 1.01654(15) 0.9266(3) 0.24966(13) 0.0217(6) Uani 1 1 d . . . C26 C 0.43295(14) 0.9978(3) 0.09522(11) 0.0184(5) Uani 1 1 d . . . C17 C 0.94338(16) 0.7504(3) 0.15001(14) 0.0224(6) Uani 1 1 d . . . C23 C 0.66214(15) 0.7764(4) 0.14153(13) 0.0191(6) Uani 1 1 d . . . C3 C 0.96511(16) 0.2381(4) 0.11006(14) 0.0240(6) Uani 1 1 d . . . C12 C 0.31651(15) 1.2007(4) 0.07008(13) 0.0254(6) Uani 1 1 d . . . C6 C 0.82833(17) 0.1997(4) -0.00851(13) 0.0268(6) Uani 1 1 d . . . C25 C 0.50382(14) 1.1045(4) 0.14133(12) 0.0182(5) Uani 1 1 d . . . C10 C 0.24253(15) 1.1909(4) 0.13628(13) 0.0287(7) Uani 1 1 d . . . C5 C 0.89960(17) 0.1697(4) -0.00968(14) 0.0329(7) Uani 1 1 d . . . C1 C 0.87598(15) 0.3137(3) 0.17189(12) 0.0193(6) Uani 1 1 d . . . C7 C 0.82799(15) 0.2480(3) 0.05334(12) 0.0193(6) Uani 1 1 d . . . C11 C 0.25605(16) 1.2669(4) 0.08362(15) 0.0302(7) Uani 1 1 d . . . C18 C 1.00934(17) 0.7235(4) 0.13850(15) 0.0281(7) Uani 1 1 d . . . C8 C 0.34886(15) 0.9869(4) 0.16219(13) 0.0235(6) Uani 1 1 d . . . C4 C 0.96641(17) 0.1897(4) 0.04800(14) 0.0300(7) Uani 1 1 d . . . C9 C 0.28804(15) 1.0511(4) 0.17590(13) 0.0280(6) Uani 1 1 d . . . H15 H 0.4959(13) 1.237(3) 0.1308(11) 0.010(6) Uiso 1 1 d . . . H11 H 0.6619(13) 0.650(4) 0.1467(11) 0.013(6) Uiso 1 1 d . . . H10 H 0.6553(12) 0.806(3) 0.0961(12) 0.009(6) Uiso 1 1 d . . . H12 H 0.5168(13) 0.767(3) 0.0532(12) 0.010(6) Uiso 1 1 d . . . H7 H 0.8059(14) 0.675(4) 0.1746(11) 0.016(6) Uiso 1 1 d . . . H9 H 0.7437(13) 0.826(3) 0.2374(12) 0.013(6) Uiso 1 1 d . . . H14 H 0.6198(14) 1.110(3) 0.1636(12) 0.015(6) Uiso 1 1 d . . . H13 H 0.5341(14) 0.610(4) 0.1089(11) 0.016(6) Uiso 1 1 d . . . H2 H 1.0154(15) 0.170(3) 0.0474(12) 0.024(7) Uiso 1 1 d . . . H8 H 0.7331(14) 1.000(4) 0.1912(12) 0.020(6) Uiso 1 1 d . . . H19 H 0.3783(14) 0.895(4) 0.1900(12) 0.016(7) Uiso 1 1 d . . . H3 H 1.0096(15) 0.246(3) 0.1501(13) 0.015(6) Uiso 1 1 d . . . H4 H 1.0078(15) 0.649(4) 0.1025(13) 0.027(7) Uiso 1 1 d . . . H1 H 0.7812(16) 0.182(4) -0.0490(14) 0.026(7) Uiso 1 1 d . . . H6 H 0.7913(15) 0.847(4) 0.1282(14) 0.031(7) Uiso 1 1 d . . . H16 H 0.5099(13) 1.095(3) 0.1877(12) 0.012(6) Uiso 1 1 d . . . H5 H 0.8958(16) 0.701(4) 0.1171(14) 0.028(7) Uiso 1 1 d . . . H18 H 0.2772(15) 1.000(4) 0.2117(13) 0.030(7) Uiso 1 1 d . . . H17 H 0.3231(15) 1.255(4) 0.0311(14) 0.030(7) Uiso 1 1 d . . . H20 H 0.4536(14) 0.759(3) 0.1518(13) 0.017(6) Uiso 1 1 d . . . H21 H 1.0186(14) 0.994(4) 0.2875(13) 0.022(7) Uiso 1 1 d . . . H22 H 0.4063(15) 0.724(3) 0.0752(13) 0.021(7) Uiso 1 1 d . . . H23 H 0.5710(14) 1.064(3) 0.0873(13) 0.024(7) Uiso 1 1 d . . . H24 H 1.1282(16) 0.946(4) 0.2685(13) 0.024(7) Uiso 1 1 d . . . H25 H 0.2243(17) 1.356(4) 0.0569(14) 0.037(8) Uiso 1 1 d . . . H26 H 0.9016(16) 0.134(4) -0.0501(14) 0.037(8) Uiso 1 1 d . . . H27 H 0.5940(16) 0.824(4) 0.1905(15) 0.034(8) Uiso 1 1 d . . . H28 H 0.382(2) 0.975(5) 0.0000(16) 0.056(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0224(4) 0.0225(4) 0.0162(3) 0.0018(3) 0.0077(3) 0.0009(3) Cl1 0.0267(4) 0.0606(5) 0.0483(5) -0.0139(4) 0.0208(4) 0.0024(4) F1 0.0280(9) 0.0474(10) 0.0409(10) 0.0041(8) 0.0228(8) 0.0053(8) O4 0.0215(10) 0.0281(10) 0.0137(8) 0.0050(8) 0.0065(8) 0.0010(8) O1 0.0257(10) 0.0267(10) 0.0143(9) -0.0033(7) 0.0061(8) -0.0045(8) O5 0.0225(10) 0.0247(10) 0.0217(9) -0.0039(8) 0.0089(8) 0.0003(8) C13 0.0169(13) 0.0215(13) 0.0147(12) -0.0013(10) 0.0036(10) -0.0028(11) O2 0.0352(11) 0.0325(11) 0.0280(10) 0.0105(9) 0.0100(9) 0.0123(9) O3 0.0257(10) 0.0336(11) 0.0204(9) 0.0026(8) 0.0076(8) -0.0074(9) N2 0.0186(11) 0.0185(11) 0.0146(11) 0.0005(9) 0.0069(9) -0.0001(9) C19 0.0262(15) 0.0295(15) 0.0300(15) 0.0084(12) 0.0178(13) 0.0058(12) C24 0.0193(14) 0.0183(14) 0.0186(13) -0.0004(11) 0.0067(11) -0.0021(11) C2 0.0292(15) 0.0143(13) 0.0170(13) 0.0009(10) 0.0105(12) -0.0024(11) C21 0.0222(14) 0.0165(15) 0.0226(14) -0.0015(11) 0.0098(12) -0.0002(11) N1 0.0250(12) 0.0210(11) 0.0173(11) -0.0022(9) 0.0104(9) 0.0008(9) C20 0.0240(14) 0.0112(12) 0.0202(13) 0.0052(10) 0.0084(11) 0.0037(10) C22 0.0222(14) 0.0208(15) 0.0176(13) 0.0015(11) 0.0083(11) 0.0016(11) C28 0.0216(14) 0.0168(14) 0.0154(13) -0.0003(10) 0.0046(11) -0.0018(11) C27 0.0204(14) 0.0205(14) 0.0174(13) 0.0012(11) 0.0056(12) -0.0030(11) C16 0.0244(14) 0.0114(12) 0.0205(13) 0.0026(10) 0.0107(11) 0.0000(10) C14 0.0206(15) 0.0263(15) 0.0248(14) 0.0046(12) 0.0063(12) 0.0007(12) C15 0.0261(15) 0.0175(13) 0.0226(14) 0.0008(11) 0.0108(12) 0.0018(11) C26 0.0212(13) 0.0214(14) 0.0125(11) 0.0017(10) 0.0067(10) -0.0003(11) C17 0.0258(15) 0.0169(13) 0.0258(14) 0.0000(11) 0.0118(13) -0.0021(11) C23 0.0232(14) 0.0189(15) 0.0186(14) 0.0011(11) 0.0120(12) 0.0020(11) C3 0.0246(15) 0.0267(15) 0.0205(14) 0.0017(11) 0.0090(13) -0.0015(12) C12 0.0247(15) 0.0279(15) 0.0231(14) 0.0016(12) 0.0091(12) -0.0005(12) C6 0.0321(17) 0.0298(16) 0.0178(14) -0.0037(12) 0.0094(13) -0.0064(13) C25 0.0227(14) 0.0164(14) 0.0171(13) 0.0014(10) 0.0095(11) 0.0005(11) C10 0.0192(14) 0.0368(17) 0.0304(15) -0.0108(13) 0.0103(12) -0.0025(12) C5 0.0413(18) 0.0409(18) 0.0238(15) -0.0075(13) 0.0207(14) -0.0037(14) C1 0.0290(15) 0.0121(13) 0.0193(14) 0.0011(10) 0.0124(12) -0.0006(11) C7 0.0239(14) 0.0182(13) 0.0165(13) 0.0009(10) 0.0089(11) -0.0010(11) C11 0.0247(16) 0.0305(17) 0.0315(16) 0.0008(13) 0.0075(13) 0.0058(13) C18 0.0369(18) 0.0256(15) 0.0289(15) -0.0018(12) 0.0207(14) 0.0013(13) C8 0.0239(15) 0.0266(15) 0.0192(13) -0.0001(12) 0.0080(12) -0.0008(12) C4 0.0291(16) 0.0382(17) 0.0279(16) -0.0038(13) 0.0169(14) -0.0004(13) C9 0.0252(15) 0.0373(17) 0.0246(14) -0.0041(13) 0.0134(13) -0.0078(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 S O2 1.4374(19) . ? S O3 1.4474(18) . ? S N1 1.609(2) . ? S C7 1.771(2) . ? Cl1 C10 1.749(3) . ? F1 C19 1.358(3) . ? O4 C26 1.430(3) . ? O4 H28 0.90(3) . ? O1 C1 1.240(3) . ? O5 C20 1.220(3) . ? C13 C12 1.391(4) . ? C13 C8 1.397(3) . ? C13 C26 1.527(3) . ? N2 C28 1.500(3) . ? N2 C24 1.503(3) . ? N2 C23 1.504(3) . ? N2 H27 0.91(3) . ? C19 C18 1.372(4) . ? C19 C14 1.376(4) . ? C24 C25 1.515(3) . ? C24 H14 0.94(3) . ? C24 H23 0.97(2) . ? C2 C7 1.379(4) . ? C2 C3 1.383(4) . ? C2 C1 1.511(3) . ? C21 C20 1.499(4) . ? C21 C22 1.527(3) . ? C21 H7 0.94(3) . ? C21 H6 0.99(3) . ? N1 C1 1.347(3) . ? C20 C16 1.502(3) . ? C22 C23 1.513(4) . ? C22 H9 0.96(2) . ? C22 H8 0.99(3) . ? C28 C27 1.513(4) . ? C28 H12 0.98(2) . ? C28 H13 0.94(3) . ? C27 C26 1.535(3) . ? C27 H20 0.96(3) . ? C27 H22 0.95(3) . ? C16 C15 1.390(3) . ? C16 C17 1.394(3) . ? C14 C15 1.375(4) . ? C14 H24 0.91(3) . ? C15 H21 0.94(2) . ? C26 C25 1.522(3) . ? C17 C18 1.391(4) . ? C17 H5 0.96(3) . ? C23 H11 0.92(3) . ? C23 H10 0.96(2) . ? C3 C4 1.393(4) . ? C3 H3 0.93(3) . ? C12 C11 1.384(4) . ? C12 H17 0.98(3) . ? C6 C7 1.381(3) . ? C6 C5 1.386(4) . ? C6 H1 0.97(3) . ? C25 H15 0.98(2) . ? C25 H16 0.96(2) . ? C10 C11 1.376(4) . ? C10 C9 1.378(4) . ? C5 C4 1.379(4) . ? C5 H26 0.92(3) . ? C11 H25 0.91(3) . ? C18 H4 0.93(3) . ? C8 C9 1.387(4) . ? C8 H19 0.92(3) . ? C4 H2 0.95(3) . ? C9 H18 0.95(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S O3 114.81(11) . . ? O2 S N1 112.35(11) . . ? O3 S N1 110.45(10) . . ? O2 S C7 110.65(11) . . ? O3 S C7 109.72(11) . . ? N1 S C7 97.52(11) . . ? C26 O4 H28 106(2) . . ? C12 C13 C8 118.0(2) . . ? C12 C13 C26 119.9(2) . . ? C8 C13 C26 121.9(2) . . ? C28 N2 C24 109.12(19) . . ? C28 N2 C23 110.15(19) . . ? C24 N2 C23 112.57(19) . . ? C28 N2 H27 108.8(18) . . ? C24 N2 H27 105.9(18) . . ? C23 N2 H27 110.2(18) . . ? F1 C19 C18 118.7(2) . . ? F1 C19 C14 118.5(2) . . ? C18 C19 C14 122.8(2) . . ? N2 C24 C25 110.63(19) . . ? N2 C24 H14 108.2(14) . . ? C25 C24 H14 111.9(14) . . ? N2 C24 H23 106.0(15) . . ? C25 C24 H23 110.9(15) . . ? H14 C24 H23 109(2) . . ? C7 C2 C3 120.2(2) . . ? C7 C2 C1 111.3(2) . . ? C3 C2 C1 128.5(2) . . ? C20 C21 C22 113.9(2) . . ? C20 C21 H7 107.9(15) . . ? C22 C21 H7 110.8(14) . . ? C20 C21 H6 109.7(15) . . ? C22 C21 H6 108.2(15) . . ? H7 C21 H6 106(2) . . ? C1 N1 S 111.43(16) . . ? O5 C20 C21 121.4(2) . . ? O5 C20 C16 120.1(2) . . ? C21 C20 C16 118.5(2) . . ? C23 C22 C21 108.9(2) . . ? C23 C22 H9 110.4(14) . . ? C21 C22 H9 110.8(14) . . ? C23 C22 H8 112.3(14) . . ? C21 C22 H8 107.4(13) . . ? H9 C22 H8 106.9(19) . . ? N2 C28 C27 111.4(2) . . ? N2 C28 H12 106.7(13) . . ? C27 C28 H12 109.1(13) . . ? N2 C28 H13 106.1(15) . . ? C27 C28 H13 112.3(14) . . ? H12 C28 H13 111.0(19) . . ? C28 C27 C26 111.7(2) . . ? C28 C27 H20 110.0(14) . . ? C26 C27 H20 108.8(14) . . ? C28 C27 H22 110.6(15) . . ? C26 C27 H22 107.8(15) . . ? H20 C27 H22 108(2) . . ? C15 C16 C17 118.9(2) . . ? C15 C16 C20 118.2(2) . . ? C17 C16 C20 122.9(2) . . ? C15 C14 C19 118.0(3) . . ? C15 C14 H24 121.1(16) . . ? C19 C14 H24 120.8(16) . . ? C14 C15 C16 121.5(2) . . ? C14 C15 H21 119.8(15) . . ? C16 C15 H21 118.7(15) . . ? O4 C26 C25 105.95(18) . . ? O4 C26 C13 110.62(19) . . ? C25 C26 C13 109.30(19) . . ? O4 C26 C27 109.13(19) . . ? C25 C26 C27 108.6(2) . . ? C13 C26 C27 112.95(19) . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H5 117.8(16) . . ? C16 C17 H5 121.9(16) . . ? N2 C23 C22 114.3(2) . . ? N2 C23 H11 104.5(14) . . ? C22 C23 H11 111.8(15) . . ? N2 C23 H10 105.6(13) . . ? C22 C23 H10 110.5(13) . . ? H11 C23 H10 109.8(19) . . ? C2 C3 C4 117.5(3) . . ? C2 C3 H3 119.9(14) . . ? C4 C3 H3 122.6(14) . . ? C11 C12 C13 121.3(3) . . ? C11 C12 H17 116.7(15) . . ? C13 C12 H17 122.0(15) . . ? C7 C6 C5 116.5(3) . . ? C7 C6 H1 122.2(15) . . ? C5 C6 H1 121.2(15) . . ? C24 C25 C26 113.0(2) . . ? C24 C25 H15 108.2(13) . . ? C26 C25 H15 109.3(14) . . ? C24 C25 H16 111.3(13) . . ? C26 C25 H16 110.0(13) . . ? H15 C25 H16 104.8(19) . . ? C11 C10 C9 121.5(2) . . ? C11 C10 Cl1 119.5(2) . . ? C9 C10 Cl1 119.1(2) . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H26 120.2(18) . . ? C6 C5 H26 118.5(18) . . ? O1 C1 N1 124.7(2) . . ? O1 C1 C2 122.1(2) . . ? N1 C1 C2 113.3(2) . . ? C2 C7 C6 123.0(2) . . ? C2 C7 S 106.47(17) . . ? C6 C7 S 130.5(2) . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H25 120.3(18) . . ? C12 C11 H25 120.5(18) . . ? C19 C18 C17 118.5(3) . . ? C19 C18 H4 121.1(16) . . ? C17 C18 H4 120.2(16) . . ? C9 C8 C13 121.2(3) . . ? C9 C8 H19 116.4(14) . . ? C13 C8 H19 122.4(14) . . ? C5 C4 C3 121.5(3) . . ? C5 C4 H2 121.7(15) . . ? C3 C4 H2 116.8(15) . . ? C10 C9 C8 118.9(2) . . ? C10 C9 H18 119.7(16) . . ? C8 C9 H18 121.4(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.458 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.069 data_grd137_a _database_code_depnum_ccdc_archive 'CCDC 253204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Quinine and Saccharin molecular complex ; _chemical_name_common 'Quinine and Saccharin molecular complex' _chemical_melting_point '185 ' _chemical_formula_moiety 'C20 H25 N2 O2, C7 H4 N O3 S' _chemical_formula_sum 'C27 H29 N3 O5 S' _chemical_formula_weight 507.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.607(3) _cell_length_b 8.634(3) _cell_length_c 30.371(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2519.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1264 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'smart 4k CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8453 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0946 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4368 _reflns_number_gt 2953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(14) _refine_ls_number_reflns 4368 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 1.0693(3) 0.3132(4) 0.85266(11) 0.0377(8) Uani 1 1 d . . . S1 S 1.18588(12) 0.49027(17) 0.12542(4) 0.0463(4) Uani 1 1 d . . . O3 O 0.4114(3) 0.4994(4) 0.80856(9) 0.0378(7) Uani 1 1 d . . . C12 C 0.7918(4) 0.5132(5) 0.78781(12) 0.0284(10) Uani 1 1 d . . . C13 C 0.9238(4) 0.4765(5) 0.80561(13) 0.0293(10) Uani 1 1 d . . . C7 C 0.6630(4) 0.4778(5) 0.80844(13) 0.0289(10) Uani 1 1 d . . . H7 H 0.6629 0.4230 0.8356 0.035 Uiso 1 1 calc R . . C19 C 1.0678(4) 0.5683(5) 0.94820(15) 0.0362(11) Uani 1 1 d . . . H19 H 1.1467 0.6389 0.9558 0.043 Uiso 1 1 calc R . . N4 N 0.8682(4) 0.3896(5) 0.92841(12) 0.0339(9) Uani 1 1 d . . . O1 O 1.0028(4) 0.2270(4) 0.05037(12) 0.0551(10) Uani 1 1 d . . . C8 C 0.5400(4) 0.5208(6) 0.79017(13) 0.0313(11) Uani 1 1 d . . . C17 C 0.9053(4) 0.4848(6) 0.88781(13) 0.0292(10) Uani 1 1 d . . . C14 C 1.0412(4) 0.5163(6) 0.78251(14) 0.0389(11) Uani 1 1 d . . . H14 H 1.1308 0.4903 0.7935 0.047 Uiso 1 1 calc R . . C10 C 0.6589(5) 0.6331(5) 0.72852(15) 0.0381(11) Uani 1 1 d . . . H10 H 0.6565 0.6839 0.7008 0.046 Uiso 1 1 calc R . . C2 C 1.0071(4) 0.5372(5) 0.12683(15) 0.0344(11) Uani 1 1 d . . . C18 C 1.0208(4) 0.5976(5) 0.90077(14) 0.0328(11) Uani 1 1 d . . . H18A H 0.9866 0.7052 0.8980 0.039 Uiso 1 1 calc R . . H18B H 1.1010 0.5847 0.8806 0.039 Uiso 1 1 calc R . . C11 C 0.7892(4) 0.5939(5) 0.74692(13) 0.0327(11) Uani 1 1 d . . . C21 C 0.8212(4) 0.5013(6) 0.96394(13) 0.0441(12) Uani 1 1 d . . . H21A H 0.7790 0.4429 0.9886 0.053 Uiso 1 1 calc R . . H21B H 0.7498 0.5724 0.9519 0.053 Uiso 1 1 calc R . . C6 C 1.0417(6) 0.3294(5) 0.07607(15) 0.0412(12) Uani 1 1 d . . . O2 O 1.2308(3) 0.4310(4) 0.16762(11) 0.0628(11) Uani 1 1 d . . . C20 C 0.9456(4) 0.5946(6) 0.98063(15) 0.0380(12) Uani 1 1 d . . . H20 H 0.9736 0.5502 1.0097 0.046 Uiso 1 1 calc R . . C9 C 0.5379(5) 0.6010(6) 0.74898(16) 0.0390(12) Uani 1 1 d . . . H9 H 0.4519 0.6313 0.7361 0.047 Uiso 1 1 calc R . . C16 C 0.9357(4) 0.3814(5) 0.84765(13) 0.0313(11) Uani 1 1 d . . . H16A H 0.8647 0.2968 0.8467 0.038 Uiso 1 1 calc R . . N3 N 1.1726(4) 0.3496(5) 0.09013(13) 0.0447(10) Uani 1 1 d . . . C24 C 0.4106(5) 0.4379(6) 0.85223(15) 0.0451(13) Uani 1 1 d . . . H24A H 0.4533 0.3348 0.8521 0.068 Uiso 1 1 calc R . . H24B H 0.3144 0.4302 0.8628 0.068 Uiso 1 1 calc R . . H24C H 0.4636 0.5065 0.8717 0.068 Uiso 1 1 calc R . . C3 C 0.9418(5) 0.4397(5) 0.09768(14) 0.0326(11) Uani 1 1 d . . . C22 C 1.1138(4) 0.4013(5) 0.95265(15) 0.0379(12) Uani 1 1 d . . . H22A H 1.1538 0.3837 0.9823 0.045 Uiso 1 1 calc R . . H22B H 1.1863 0.3777 0.9305 0.045 Uiso 1 1 calc R . . C25 C 0.9134(5) 0.7603(6) 0.98754(18) 0.0506(14) Uani 1 1 d . . . H35 H 0.8671 0.8142 0.9645 0.061 Uiso 1 1 calc R . . C23 C 0.9872(4) 0.2952(5) 0.94570(15) 0.0375(11) Uani 1 1 d . . . H23A H 1.0107 0.2122 0.9245 0.045 Uiso 1 1 calc R . . H23B H 0.9606 0.2461 0.9739 0.045 Uiso 1 1 calc R . . C5 C 0.7267(6) 0.5544(6) 0.1185(2) 0.0604(16) Uani 1 1 d . . . H5 H 0.6283 0.5611 0.1161 0.072 Uiso 1 1 calc R . . C15 C 1.0272(5) 0.5960(6) 0.74244(16) 0.0452(13) Uani 1 1 d . . . H15 H 1.1099 0.6258 0.7275 0.054 Uiso 1 1 calc R . . C26 C 0.9445(6) 0.8377(7) 1.0234(2) 0.0657(17) Uani 1 1 d . . . H26A H 0.9907 0.7872 1.0470 0.079 Uiso 1 1 calc R . . H26B H 0.9207 0.9442 1.0257 0.079 Uiso 1 1 calc R . . C1 C 0.9378(5) 0.6441(5) 0.15239(17) 0.0462(13) Uani 1 1 d . . . H1 H 0.9858 0.7100 0.1723 0.055 Uiso 1 1 calc R . . C4 C 0.7977(5) 0.4496(6) 0.09303(18) 0.0485(13) Uani 1 1 d . . . H4 H 0.7498 0.3853 0.0727 0.058 Uiso 1 1 calc R . . C27 C 0.7960(6) 0.6505(7) 0.1477(2) 0.0619(16) Uani 1 1 d . . . H27 H 0.7441 0.7224 0.1648 0.074 Uiso 1 1 calc R . . O5 O 1.2632(4) 0.6181(5) 0.10827(14) 0.0780(13) Uani 1 1 d . . . N5 N 0.9077(4) 0.6320(5) 0.72428(12) 0.0412(10) Uani 1 1 d . . . H25 H 0.821(3) 0.540(3) 0.8815(10) 0.004(8) Uiso 1 1 d . . . H31 H 0.790(6) 0.317(8) 0.920(2) 0.11(2) Uiso 1 1 d . . . H51 H 1.076(5) 0.259(6) 0.8333(17) 0.055(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0346(19) 0.052(2) 0.0266(19) -0.0060(18) -0.0020(15) 0.0108(16) S1 0.0367(7) 0.0589(8) 0.0434(7) 0.0003(7) -0.0024(6) -0.0007(7) O3 0.0309(16) 0.0489(19) 0.0336(17) 0.0026(18) -0.0018(13) -0.0021(16) C12 0.030(2) 0.030(2) 0.025(2) -0.003(2) 0.0005(18) 0.001(2) C13 0.028(2) 0.034(3) 0.026(2) -0.005(2) 0.0013(18) 0.006(2) C7 0.029(2) 0.037(3) 0.020(2) -0.003(2) -0.0020(18) -0.004(2) C19 0.029(3) 0.045(3) 0.035(3) -0.007(2) -0.004(2) -0.004(2) N4 0.032(2) 0.046(2) 0.024(2) -0.0009(18) 0.0062(16) -0.006(2) O1 0.084(3) 0.042(2) 0.039(2) -0.0100(18) -0.006(2) 0.0058(19) C8 0.031(2) 0.038(3) 0.025(2) -0.002(2) 0.000(2) -0.001(2) C17 0.025(2) 0.040(3) 0.023(2) 0.000(2) 0.0002(17) 0.005(2) C14 0.030(2) 0.055(3) 0.031(2) -0.003(3) 0.002(2) 0.002(3) C10 0.043(3) 0.046(3) 0.026(3) 0.008(2) -0.007(2) 0.004(2) C2 0.042(3) 0.026(3) 0.036(2) 0.002(2) -0.003(2) -0.001(2) C18 0.031(2) 0.039(3) 0.029(2) 0.000(2) 0.004(2) 0.001(2) C11 0.042(3) 0.036(3) 0.020(2) 0.002(2) 0.001(2) 0.001(2) C21 0.042(3) 0.061(3) 0.030(2) -0.011(3) 0.012(2) 0.007(3) C6 0.067(4) 0.031(3) 0.026(3) 0.004(2) 0.002(3) 0.003(3) O2 0.054(2) 0.086(3) 0.048(2) -0.007(2) -0.0227(18) 0.021(2) C20 0.039(3) 0.045(3) 0.030(3) -0.004(2) -0.008(2) 0.004(2) C9 0.032(3) 0.046(3) 0.039(3) 0.008(2) -0.008(2) 0.003(2) C16 0.020(2) 0.048(3) 0.025(2) -0.004(2) -0.0006(18) -0.001(2) N3 0.044(3) 0.051(3) 0.039(2) -0.002(2) 0.001(2) 0.010(2) C24 0.035(3) 0.060(3) 0.040(3) 0.010(3) 0.006(2) -0.006(2) C3 0.043(3) 0.024(2) 0.031(2) 0.006(2) -0.001(2) 0.001(2) C22 0.036(3) 0.046(3) 0.031(3) -0.002(2) -0.006(2) 0.001(2) C25 0.051(3) 0.057(4) 0.044(3) -0.006(3) 0.008(3) 0.004(3) C23 0.046(3) 0.040(3) 0.026(3) 0.001(2) -0.003(2) 0.002(2) C5 0.038(3) 0.058(4) 0.085(4) 0.012(3) -0.004(3) 0.015(3) C15 0.034(3) 0.062(3) 0.039(3) 0.010(3) 0.011(2) -0.007(3) C26 0.073(4) 0.050(4) 0.074(4) -0.022(3) 0.004(3) 0.004(3) C1 0.060(3) 0.031(3) 0.048(3) -0.002(2) -0.008(3) 0.008(2) C4 0.042(3) 0.042(3) 0.062(3) 0.003(3) -0.018(3) 0.001(2) C27 0.063(4) 0.053(4) 0.070(4) -0.001(3) 0.005(3) 0.028(3) O5 0.064(3) 0.083(3) 0.087(3) 0.003(2) 0.008(2) -0.031(2) N5 0.042(2) 0.056(3) 0.026(2) 0.004(2) 0.0073(19) -0.004(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 O4 C16 1.420(5) . ? O4 H51 0.76(5) . ? S1 O5 1.428(4) . ? S1 O2 1.446(4) . ? S1 N3 1.625(4) . ? S1 C2 1.765(4) . ? O3 C8 1.368(5) . ? O3 C24 1.429(5) . ? C12 C13 1.414(5) . ? C12 C7 1.421(5) . ? C12 C11 1.424(6) . ? C13 C14 1.372(6) . ? C13 C16 1.522(6) . ? C7 C8 1.357(5) . ? C7 H7 0.9500 . ? C19 C22 1.514(6) . ? C19 C18 1.530(6) . ? C19 C20 1.549(6) . ? C19 H19 1.0000 . ? N4 C23 1.499(5) . ? N4 C21 1.516(5) . ? N4 C17 1.524(5) . ? N4 H31 1.01(7) . ? O1 C6 1.237(5) . ? C8 C9 1.430(6) . ? C17 C18 1.529(6) . ? C17 C16 1.540(6) . ? C17 H25 0.96(3) . ? C14 C15 1.405(7) . ? C14 H14 0.9500 . ? C10 C9 1.347(6) . ? C10 C11 1.412(6) . ? C10 H10 0.9500 . ? C2 C3 1.374(6) . ? C2 C1 1.378(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C11 N5 1.370(5) . ? C21 C20 1.528(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C6 N3 1.339(6) . ? C6 C3 1.503(6) . ? C20 C25 1.479(7) . ? C20 H20 1.0000 . ? C9 H9 0.9500 . ? C16 H16A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C3 C4 1.394(6) . ? C22 C23 1.538(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C25 C26 1.311(7) . ? C25 H35 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C5 C4 1.372(7) . ? C5 C27 1.384(7) . ? C5 H5 0.9500 . ? C15 N5 1.311(6) . ? C15 H15 0.9500 . ? C26 H26A 0.9500 . ? C26 H26B 0.9500 . ? C1 C27 1.371(7) . ? C1 H1 0.9500 . ? C4 H4 0.9500 . ? C27 H27 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 C16 O4 H51 105(4) . . ? O5 S1 O2 116.2(2) . . ? O5 S1 N3 112.2(2) . . ? O2 S1 N3 110.1(2) . . ? O5 S1 C2 109.7(2) . . ? O2 S1 C2 110.5(2) . . ? N3 S1 C2 96.4(2) . . ? C8 O3 C24 115.7(3) . . ? C13 C12 C7 124.3(4) . . ? C13 C12 C11 117.3(4) . . ? C7 C12 C11 118.3(4) . . ? C14 C13 C12 119.0(4) . . ? C14 C13 C16 120.1(4) . . ? C12 C13 C16 120.6(4) . . ? C8 C7 C12 121.3(4) . . ? C8 C7 H7 119.4 . . ? C12 C7 H7 119.4 . . ? C22 C19 C18 109.1(4) . . ? C22 C19 C20 107.7(4) . . ? C18 C19 C20 110.5(4) . . ? C22 C19 H19 109.8 . . ? C18 C19 H19 109.8 . . ? C20 C19 H19 109.8 . . ? C23 N4 C21 108.9(3) . . ? C23 N4 C17 113.5(3) . . ? C21 N4 C17 107.6(4) . . ? C23 N4 H31 108(4) . . ? C21 N4 H31 110(4) . . ? C17 N4 H31 108(4) . . ? C7 C8 O3 125.6(4) . . ? C7 C8 C9 120.2(4) . . ? O3 C8 C9 114.2(4) . . ? N4 C17 C18 107.7(3) . . ? N4 C17 C16 111.9(4) . . ? C18 C17 C16 115.8(3) . . ? N4 C17 H25 103.3(18) . . ? C18 C17 H25 110.5(18) . . ? C16 C17 H25 106.9(18) . . ? C13 C14 C15 119.2(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C9 C10 C11 122.2(4) . . ? C9 C10 H10 118.9 . . ? C11 C10 H10 118.9 . . ? C3 C2 C1 123.6(4) . . ? C3 C2 S1 106.7(3) . . ? C1 C2 S1 129.7(4) . . ? C17 C18 C19 110.6(4) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? N5 C11 C10 118.7(4) . . ? N5 C11 C12 122.7(4) . . ? C10 C11 C12 118.6(4) . . ? N4 C21 C20 109.8(3) . . ? N4 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? N4 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? O1 C6 N3 125.3(5) . . ? O1 C6 C3 122.3(5) . . ? N3 C6 C3 112.2(4) . . ? C25 C20 C21 113.1(4) . . ? C25 C20 C19 113.0(4) . . ? C21 C20 C19 107.7(3) . . ? C25 C20 H20 107.6 . . ? C21 C20 H20 107.6 . . ? C19 C20 H20 107.6 . . ? C10 C9 C8 119.4(4) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O4 C16 C13 112.4(3) . . ? O4 C16 C17 109.1(3) . . ? C13 C16 C17 109.7(4) . . ? O4 C16 H16A 108.5 . . ? C13 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C6 N3 S1 112.4(3) . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2 C3 C4 118.8(4) . . ? C2 C3 C6 112.2(4) . . ? C4 C3 C6 129.0(4) . . ? C19 C22 C23 108.9(3) . . ? C19 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? C19 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? C26 C25 C20 124.2(5) . . ? C26 C25 H35 117.9 . . ? C20 C25 H35 117.9 . . ? N4 C23 C22 109.1(4) . . ? N4 C23 H23A 109.9 . . ? C22 C23 H23A 109.9 . . ? N4 C23 H23B 109.9 . . ? C22 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? C4 C5 C27 121.1(5) . . ? C4 C5 H5 119.4 . . ? C27 C5 H5 119.4 . . ? N5 C15 C14 124.3(4) . . ? N5 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? C25 C26 H26A 120.0 . . ? C25 C26 H26B 120.0 . . ? H26A C26 H26B 120.0 . . ? C27 C1 C2 116.7(5) . . ? C27 C1 H1 121.7 . . ? C2 C1 H1 121.7 . . ? C5 C4 C3 118.5(5) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C1 C27 C5 121.4(5) . . ? C1 C27 H27 119.3 . . ? C5 C27 H27 119.3 . . ? C15 N5 C11 117.4(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.505 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.062