Supplementary information (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Raj Suryanarayan' ; Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Weaver-Densford Hall, 308 Harvard St. SE, Minneapolis, MN 55455-0343 ; 'Enxian Lu' ; Department of Pharmaceutical Sciences, College of Pharmacy, University of Michigan, 428 Church Street , Ann Arbor, MI 48109-1065 ; 'Nair Rodriguez-Hornedo' '' _publ_contact_author_name 'Raj Suryanarayanan' _publ_contact_author_address ; University of Minnesota Minneapolis 55455 UNITED STATES OF AMERICA ; _publ_contact_author_email SURYA001@UMN.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; A rapid thermal method for cocrystal screening ; data_CAF-SAA _database_code_depnum_ccdc_archive 'CCDC 671496' _audit_creation_method SHELXL-97 _chemical_name_systematic ; caffeine salicylic acid cocrystal ; _chemical_name_common cafsaa _chemical_melting_point 142C _chemical_formula_moiety 'C8 H10 N4 O2, C7 H6 O3' _chemical_formula_sum 'C15 H16 N4 O5' _chemical_formula_weight 332.32 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' _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 14.728(2) _cell_length_b 6.9970(11) _cell_length_c 16.148(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.074(2) _cell_angle_gamma 90.00 _cell_volume 1481.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3157 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 24.83 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9451 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10988 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2623 _reflns_number_gt 1990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0715P)^2^+0.6481P] 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 2623 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O 0.10053(12) 0.4406(2) 0.28181(11) 0.0374(4) Uani 1 1 d . . . O2 O 0.18357(12) 0.5329(2) 0.58866(11) 0.0310(4) Uani 1 1 d . . . O3 O 0.54297(11) 0.1882(2) 0.43557(10) 0.0307(4) Uani 1 1 d . . . H3O H 0.5007(18) 0.226(3) 0.4659(16) 0.037 Uiso 1 1 d . . . O4 O 0.66461(12) 0.1703(2) 0.58215(10) 0.0336(4) Uani 1 1 d . . . O5 O 0.84207(13) 0.0450(2) 0.61622(11) 0.0362(4) Uani 1 1 d . . . H5O H 0.785(2) 0.087(4) 0.6246(18) 0.043 Uiso 1 1 d . . . N1 N 0.39897(13) 0.3925(2) 0.62965(12) 0.0243(4) Uani 1 1 d . . . N2 N 0.43077(13) 0.3047(2) 0.51312(12) 0.0260(4) Uani 1 1 d . . . N3 N 0.26392(13) 0.3736(2) 0.38666(12) 0.0253(4) Uani 1 1 d . . . N4 N 0.14511(13) 0.4931(2) 0.43485(12) 0.0262(4) Uani 1 1 d . . . C1 C 0.41475(18) 0.4330(4) 0.72370(15) 0.0341(6) Uani 1 1 d . . . H1A H 0.4847 0.3993 0.7682 0.051 Uiso 1 1 calc R . . H1B H 0.3667 0.3578 0.7369 0.051 Uiso 1 1 calc R . . H1C H 0.4034 0.5694 0.7293 0.051 Uiso 1 1 calc R . . C2 C 0.46714(16) 0.3216(3) 0.60523(15) 0.0260(5) Uani 1 1 d . . . H2A H 0.5345 0.2867 0.6486 0.031 Uiso 1 1 calc R . . C3 C 0.33331(15) 0.3681(3) 0.47853(14) 0.0224(5) Uani 1 1 d . . . C4 C 0.29233(18) 0.3107(4) 0.31527(15) 0.0338(6) Uani 1 1 d . . . H4A H 0.3216 0.1820 0.3303 0.051 Uiso 1 1 calc R . . H4B H 0.3427 0.3991 0.3130 0.051 Uiso 1 1 calc R . . H4C H 0.2316 0.3087 0.2547 0.051 Uiso 1 1 calc R . . C5 C 0.16606(17) 0.4352(3) 0.36231(15) 0.0266(5) Uani 1 1 d . . . C6 C 0.04083(17) 0.5577(4) 0.40674(17) 0.0363(6) Uani 1 1 d . . . H6A H 0.0188 0.6404 0.3520 0.054 Uiso 1 1 calc R . . H6B H 0.0383 0.6292 0.4578 0.054 Uiso 1 1 calc R . . H6C H -0.0046 0.4467 0.3915 0.054 Uiso 1 1 calc R . . C7 C 0.21213(16) 0.4883(3) 0.53135(15) 0.0245(5) Uani 1 1 d . . . C8 C 0.31051(15) 0.4244(3) 0.54788(14) 0.0224(5) Uani 1 1 d . . . C9 C 0.63553(16) 0.1481(3) 0.49783(15) 0.0256(5) Uani 1 1 d . . . C10 C 0.70381(16) 0.0754(3) 0.46108(15) 0.0250(5) Uani 1 1 d . . . C11 C 0.80501(17) 0.0277(3) 0.52287(16) 0.0278(5) Uani 1 1 d . . . C12 C 0.86943(18) -0.0413(3) 0.48825(18) 0.0334(6) Uani 1 1 d . . . H12A H 0.9377 -0.0753 0.5298 0.040 Uiso 1 1 calc R . . C13 C 0.83468(18) -0.0606(3) 0.39426(18) 0.0356(6) Uani 1 1 d . . . H13A H 0.8794 -0.1079 0.3713 0.043 Uiso 1 1 calc R . . C14 C 0.73538(19) -0.0122(3) 0.33197(17) 0.0333(6) Uani 1 1 d . . . H14A H 0.7126 -0.0241 0.2669 0.040 Uiso 1 1 calc R . . C15 C 0.67029(17) 0.0533(3) 0.36557(16) 0.0283(5) Uani 1 1 d . . . H15A H 0.6018 0.0838 0.3233 0.034 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 O1 0.0326(9) 0.0449(10) 0.0236(9) -0.0008(7) 0.0029(8) 0.0022(7) O2 0.0312(9) 0.0321(9) 0.0325(9) 0.0000(7) 0.0170(7) 0.0018(7) O3 0.0263(9) 0.0366(9) 0.0283(9) -0.0014(7) 0.0116(7) 0.0041(7) O4 0.0352(9) 0.0399(9) 0.0245(9) 0.0009(7) 0.0126(7) 0.0044(7) O5 0.0302(9) 0.0440(10) 0.0283(9) 0.0067(8) 0.0082(8) 0.0035(7) N1 0.0228(9) 0.0243(9) 0.0214(10) 0.0012(7) 0.0064(8) -0.0005(7) N2 0.0245(10) 0.0258(10) 0.0262(10) 0.0008(8) 0.0101(8) -0.0008(8) N3 0.0257(10) 0.0263(9) 0.0209(10) -0.0007(8) 0.0079(8) -0.0010(8) N4 0.0233(10) 0.0258(9) 0.0265(10) 0.0016(8) 0.0087(8) 0.0007(7) C1 0.0363(14) 0.0381(14) 0.0223(12) -0.0031(10) 0.0085(11) 0.0007(10) C2 0.0195(11) 0.0277(11) 0.0257(12) 0.0026(9) 0.0058(9) -0.0003(9) C3 0.0234(11) 0.0180(10) 0.0239(11) 0.0002(8) 0.0092(9) -0.0035(8) C4 0.0400(14) 0.0374(13) 0.0263(12) -0.0019(10) 0.0171(11) -0.0001(11) C5 0.0271(12) 0.0223(11) 0.0248(13) 0.0015(9) 0.0070(10) -0.0024(9) C6 0.0256(13) 0.0413(14) 0.0376(14) 0.0011(11) 0.0106(11) 0.0034(10) C7 0.0293(12) 0.0189(10) 0.0250(12) 0.0011(9) 0.0122(10) -0.0017(9) C8 0.0227(11) 0.0200(10) 0.0215(11) 0.0009(9) 0.0075(9) -0.0025(8) C9 0.0272(12) 0.0216(11) 0.0256(13) 0.0012(9) 0.0099(10) -0.0014(9) C10 0.0260(12) 0.0203(11) 0.0283(12) 0.0001(9) 0.0121(10) -0.0034(9) C11 0.0282(12) 0.0224(11) 0.0312(13) 0.0027(9) 0.0120(10) -0.0034(9) C12 0.0268(12) 0.0302(12) 0.0432(15) 0.0082(11) 0.0161(11) 0.0003(10) C13 0.0374(14) 0.0306(13) 0.0491(16) 0.0025(11) 0.0287(13) 0.0018(10) C14 0.0418(14) 0.0301(12) 0.0328(13) -0.0001(10) 0.0214(12) -0.0026(10) C15 0.0290(12) 0.0240(11) 0.0296(13) 0.0012(9) 0.0113(10) -0.0005(9) _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 C5 1.217(3) . ? O2 C7 1.219(3) . ? O3 C9 1.304(3) . ? O3 H3O 0.99(2) . ? O4 C9 1.237(3) . ? O5 C11 1.355(3) . ? O5 H5O 0.96(3) . ? N1 C2 1.330(3) . ? N1 C8 1.387(3) . ? N1 C1 1.456(3) . ? N2 C2 1.337(3) . ? N2 C3 1.356(3) . ? N3 C3 1.366(3) . ? N3 C5 1.379(3) . ? N3 C4 1.462(3) . ? N4 C5 1.400(3) . ? N4 C7 1.415(3) . ? N4 C6 1.461(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9500 . ? C3 C8 1.365(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.421(3) . ? C9 C10 1.472(3) . ? C10 C15 1.398(3) . ? C10 C11 1.405(3) . ? C11 C12 1.389(3) . ? C12 C13 1.370(3) . ? C12 H12A 0.9500 . ? C13 C14 1.388(3) . ? C13 H13A 0.9500 . ? C14 C15 1.377(3) . ? C14 H14A 0.9500 . ? C15 H15A 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 C9 O3 H3O 110.5(13) . . ? C11 O5 H5O 104.4(16) . . ? C2 N1 C8 106.63(17) . . ? C2 N1 C1 126.74(18) . . ? C8 N1 C1 126.61(18) . . ? C2 N2 C3 104.01(17) . . ? C3 N3 C5 119.11(18) . . ? C3 N3 C4 120.45(18) . . ? C5 N3 C4 120.42(18) . . ? C5 N4 C7 127.27(18) . . ? C5 N4 C6 115.49(18) . . ? C7 N4 C6 117.19(18) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 112.86(18) . . ? N1 C2 H2A 123.6 . . ? N2 C2 H2A 123.6 . . ? N2 C3 C8 111.46(19) . . ? N2 C3 N3 125.79(19) . . ? C8 C3 N3 122.74(19) . . ? N3 C4 H4A 109.5 . . ? N3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C5 N3 122.1(2) . . ? O1 C5 N4 121.0(2) . . ? N3 C5 N4 116.84(18) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C7 N4 121.41(19) . . ? O2 C7 C8 127.8(2) . . ? N4 C7 C8 110.77(18) . . ? C3 C8 N1 105.03(18) . . ? C3 C8 C7 123.18(19) . . ? N1 C8 C7 131.68(19) . . ? O4 C9 O3 122.57(19) . . ? O4 C9 C10 122.0(2) . . ? O3 C9 C10 115.46(19) . . ? C15 C10 C11 119.0(2) . . ? C15 C10 C9 121.4(2) . . ? C11 C10 C9 119.6(2) . . ? O5 C11 C12 118.4(2) . . ? O5 C11 C10 121.9(2) . . ? C12 C11 C10 119.7(2) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C15 C14 C13 119.2(2) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C10 120.8(2) . . ? C14 C15 H15A 119.6 . . ? C10 C15 H15A 119.6 . . ? 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 C8 N1 C2 N2 0.3(2) . . . . ? C1 N1 C2 N2 -178.38(19) . . . . ? C3 N2 C2 N1 -0.5(2) . . . . ? C2 N2 C3 C8 0.5(2) . . . . ? C2 N2 C3 N3 -178.2(2) . . . . ? C5 N3 C3 N2 177.49(18) . . . . ? C4 N3 C3 N2 -1.1(3) . . . . ? C5 N3 C3 C8 -1.1(3) . . . . ? C4 N3 C3 C8 -179.70(19) . . . . ? C3 N3 C5 O1 -178.9(2) . . . . ? C4 N3 C5 O1 -0.3(3) . . . . ? C3 N3 C5 N4 1.5(3) . . . . ? C4 N3 C5 N4 -179.98(18) . . . . ? C7 N4 C5 O1 177.6(2) . . . . ? C6 N4 C5 O1 0.3(3) . . . . ? C7 N4 C5 N3 -2.8(3) . . . . ? C6 N4 C5 N3 179.96(18) . . . . ? C5 N4 C7 O2 -175.92(19) . . . . ? C6 N4 C7 O2 1.3(3) . . . . ? C5 N4 C7 C8 3.3(3) . . . . ? C6 N4 C7 C8 -179.53(18) . . . . ? N2 C3 C8 N1 -0.4(2) . . . . ? N3 C3 C8 N1 178.44(18) . . . . ? N2 C3 C8 C7 -176.90(18) . . . . ? N3 C3 C8 C7 1.9(3) . . . . ? C2 N1 C8 C3 0.1(2) . . . . ? C1 N1 C8 C3 178.7(2) . . . . ? C2 N1 C8 C7 176.2(2) . . . . ? C1 N1 C8 C7 -5.2(4) . . . . ? O2 C7 C8 C3 176.4(2) . . . . ? N4 C7 C8 C3 -2.7(3) . . . . ? O2 C7 C8 N1 0.9(4) . . . . ? N4 C7 C8 N1 -178.2(2) . . . . ? O4 C9 C10 C15 -179.2(2) . . . . ? O3 C9 C10 C15 0.4(3) . . . . ? O4 C9 C10 C11 0.6(3) . . . . ? O3 C9 C10 C11 -179.83(18) . . . . ? C15 C10 C11 O5 -179.67(18) . . . . ? C9 C10 C11 O5 0.6(3) . . . . ? C15 C10 C11 C12 -0.4(3) . . . . ? C9 C10 C11 C12 179.83(19) . . . . ? O5 C11 C12 C13 -179.9(2) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 -1.1(3) . . . . ? C13 C14 C15 C10 1.5(3) . . . . ? C11 C10 C15 C14 -0.7(3) . . . . ? C9 C10 C15 C14 179.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O N2 0.99(2) 1.63(3) 2.617(2) 176(2) . O5 H5O O4 0.96(3) 1.68(3) 2.568(2) 151(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.292 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.072 # Attachment 'CBZ-MAA.cif' data_CBA-MAA _database_code_depnum_ccdc_archive 'CCDC 671497' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cbzmaa _chemical_melting_point ? _chemical_formula_moiety '2(C15 H12 N2 O), C3 H3 O4' _chemical_formula_sum 'C33 H27 N4 O6' _chemical_formula_weight 575.59 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 17.206(4) _cell_length_b 4.9926(11) _cell_length_c 18.270(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.440(3) _cell_angle_gamma 90.00 _cell_volume 1392.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2111 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.44 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9625 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15846 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2848 _reflns_number_gt 2189 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0497P)^2^+0.6243P] 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 2848 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.84652(8) 0.0255(3) 0.57256(8) 0.0259(3) Uani 1 1 d . . . C1 C 0.76243(10) -0.0453(4) 0.56579(10) 0.0253(4) Uani 1 1 d . . . C2 C 0.71449(11) -0.2514(4) 0.51365(11) 0.0317(4) Uani 1 1 d . . . H2A H 0.7369 -0.3445 0.4820 0.038 Uiso 1 1 calc R . . C3 C 0.63406(12) -0.3213(4) 0.50773(12) 0.0358(5) Uani 1 1 d . . . H3A H 0.6013 -0.4633 0.4724 0.043 Uiso 1 1 calc R . . C4 C 0.60149(12) -0.1843(4) 0.55337(12) 0.0392(5) Uani 1 1 d . . . H4A H 0.5461 -0.2318 0.5492 0.047 Uiso 1 1 calc R . . C5 C 0.64921(12) 0.0215(4) 0.60502(12) 0.0363(5) Uani 1 1 d . . . H5A H 0.6259 0.1150 0.6357 0.044 Uiso 1 1 calc R . . C6 C 0.73155(11) 0.0955(4) 0.61308(10) 0.0282(4) Uani 1 1 d . . . C7 C 0.78023(11) 0.3134(4) 0.66888(10) 0.0302(4) Uani 1 1 d . . . H7A H 0.7466 0.4568 0.6736 0.036 Uiso 1 1 calc R . . C8 C 0.86719(11) 0.3321(4) 0.71396(11) 0.0304(4) Uani 1 1 d . . . H8A H 0.8891 0.4896 0.7462 0.037 Uiso 1 1 calc R . . C9 C 0.93168(10) 0.1341(4) 0.71847(10) 0.0265(4) Uani 1 1 d . . . C10 C 1.00692(12) 0.0882(4) 0.79341(11) 0.0348(4) Uani 1 1 d . . . H10A H 1.0173 0.1962 0.8398 0.042 Uiso 1 1 calc R . . C11 C 1.06597(12) -0.1091(4) 0.80131(12) 0.0381(5) Uani 1 1 d . . . H11A H 1.1161 -0.1373 0.8529 0.046 Uiso 1 1 calc R . . C12 C 1.05245(12) -0.2663(4) 0.73432(12) 0.0360(5) Uani 1 1 d . . . H12A H 1.0928 -0.4044 0.7399 0.043 Uiso 1 1 calc R . . C13 C 0.97991(11) -0.2223(4) 0.65901(11) 0.0309(4) Uani 1 1 d . . . H13A H 0.9706 -0.3293 0.6127 0.037 Uiso 1 1 calc R . . C14 C 0.92109(10) -0.0221(4) 0.65137(10) 0.0250(4) Uani 1 1 d . . . C15 C 0.85182(11) 0.1473(4) 0.50836(10) 0.0254(4) Uani 1 1 d . . . N2 N 0.93116(9) 0.2230(3) 0.51865(9) 0.0329(4) Uani 1 1 d . . . H2B H 0.9363 0.3053 0.4785 0.039 Uiso 1 1 calc R . . H2C H 0.9780 0.1903 0.5656 0.039 Uiso 1 1 calc R . . O1 O 0.78404(8) 0.1897(3) 0.44308(7) 0.0327(3) Uani 1 1 d . . . C16 C 0.7500 0.8858(5) 0.2500 0.0304(6) Uani 1 2 d S . . H16A H 0.7094 0.9976 0.2583 0.037 Uiso 0.50 1 d PR . . C17 C 0.79635(11) 0.7091(4) 0.32509(10) 0.0263(4) Uani 1 1 d . . . O2 O 0.87415(8) 0.7111(3) 0.37164(8) 0.0397(4) Uani 1 1 d . . . O3 O 0.74039(8) 0.5479(3) 0.33274(7) 0.0362(3) Uani 1 1 d . . . H3B H 0.7676 0.4387 0.3711 0.054 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 N1 0.0172(7) 0.0368(9) 0.0192(7) 0.0027(6) 0.0045(6) 0.0007(6) C1 0.0184(8) 0.0322(10) 0.0195(8) 0.0069(7) 0.0038(7) 0.0029(7) C2 0.0268(9) 0.0366(10) 0.0250(9) 0.0034(8) 0.0063(8) 0.0026(8) C3 0.0248(9) 0.0384(11) 0.0309(10) 0.0075(9) 0.0015(8) -0.0045(8) C4 0.0209(9) 0.0493(13) 0.0412(11) 0.0123(10) 0.0090(8) -0.0014(9) C5 0.0241(9) 0.0489(12) 0.0357(10) 0.0081(9) 0.0135(8) 0.0072(9) C6 0.0224(8) 0.0340(10) 0.0252(9) 0.0079(8) 0.0084(7) 0.0057(8) C7 0.0296(9) 0.0341(10) 0.0261(9) 0.0042(8) 0.0121(8) 0.0072(8) C8 0.0328(10) 0.0324(10) 0.0237(9) 0.0000(8) 0.0110(8) -0.0011(8) C9 0.0205(8) 0.0324(10) 0.0234(9) 0.0021(7) 0.0074(7) -0.0024(7) C10 0.0275(9) 0.0474(12) 0.0229(9) -0.0007(8) 0.0059(8) -0.0054(9) C11 0.0197(9) 0.0519(13) 0.0303(10) 0.0122(9) 0.0011(8) 0.0001(9) C12 0.0210(9) 0.0381(11) 0.0438(11) 0.0097(9) 0.0106(8) 0.0051(8) C13 0.0230(9) 0.0338(10) 0.0334(10) 0.0009(8) 0.0110(8) -0.0002(8) C14 0.0180(8) 0.0306(10) 0.0213(8) 0.0042(7) 0.0048(7) -0.0009(7) C15 0.0237(8) 0.0294(9) 0.0198(8) -0.0036(7) 0.0073(7) -0.0010(7) N2 0.0252(8) 0.0471(10) 0.0234(8) 0.0005(7) 0.0088(6) -0.0076(7) O1 0.0270(7) 0.0430(8) 0.0195(6) 0.0035(6) 0.0034(5) -0.0048(6) C16 0.0295(13) 0.0303(14) 0.0296(13) 0.000 0.0121(11) 0.000 C17 0.0225(9) 0.0320(10) 0.0233(9) -0.0085(7) 0.0096(7) -0.0035(7) O2 0.0211(7) 0.0552(9) 0.0334(7) -0.0028(7) 0.0047(6) -0.0046(6) O3 0.0248(6) 0.0469(9) 0.0270(7) 0.0080(6) 0.0035(5) -0.0078(6) _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 C15 1.361(2) . ? N1 C1 1.438(2) . ? N1 C14 1.440(2) . ? C1 C2 1.387(3) . ? C1 C6 1.395(2) . ? C2 C3 1.382(3) . ? C2 H2A 0.9500 . ? C3 C4 1.381(3) . ? C3 H3A 0.9500 . ? C4 C5 1.381(3) . ? C4 H4A 0.9500 . ? C5 C6 1.405(2) . ? C5 H5A 0.9500 . ? C6 C7 1.462(3) . ? C7 C8 1.338(2) . ? C7 H7A 0.9500 . ? C8 C9 1.460(3) . ? C8 H8A 0.9500 . ? C9 C14 1.392(2) . ? C9 C10 1.404(2) . ? C10 C11 1.374(3) . ? C10 H10A 0.9500 . ? C11 C12 1.380(3) . ? C11 H11A 0.9500 . ? C12 C13 1.384(3) . ? C12 H12A 0.9500 . ? C13 C14 1.383(2) . ? C13 H13A 0.9500 . ? C15 O1 1.243(2) . ? C15 N2 1.344(2) . ? N2 H2B 0.8800 . ? N2 H2C 0.8800 . ? C16 C17 1.513(2) 2_655 ? C16 C17 1.513(2) . ? C16 H16A 0.9600 . ? C17 O2 1.211(2) . ? C17 O3 1.311(2) . ? O3 H3B 0.8400 . ? 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 C15 N1 C1 119.99(13) . . ? C15 N1 C14 123.57(14) . . ? C1 N1 C14 116.29(13) . . ? C2 C1 C6 121.58(16) . . ? C2 C1 N1 119.86(16) . . ? C6 C1 N1 118.56(15) . . ? C3 C2 C1 119.88(18) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C4 C3 C2 119.86(19) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.14(18) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C4 C5 C6 121.40(18) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C1 C6 C5 117.14(17) . . ? C1 C6 C7 123.19(16) . . ? C5 C6 C7 119.67(17) . . ? C8 C7 C6 126.89(17) . . ? C8 C7 H7A 116.6 . . ? C6 C7 H7A 116.6 . . ? C7 C8 C9 126.35(17) . . ? C7 C8 H8A 116.8 . . ? C9 C8 H8A 116.8 . . ? C14 C9 C10 117.06(17) . . ? C14 C9 C8 122.83(15) . . ? C10 C9 C8 120.08(16) . . ? C11 C10 C9 121.64(18) . . ? C11 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? C10 C11 C12 120.01(17) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 119.81(18) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C14 C13 C12 119.86(18) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C9 121.56(16) . . ? C13 C14 N1 119.59(16) . . ? C9 C14 N1 118.85(15) . . ? O1 C15 N2 121.99(16) . . ? O1 C15 N1 119.81(15) . . ? N2 C15 N1 118.18(15) . . ? C15 N2 H2B 120.0 . . ? C15 N2 H2C 120.0 . . ? H2B N2 H2C 120.0 . . ? C17 C16 C17 108.6(2) 2_655 . ? C17 C16 H16A 111.4 2_655 . ? C17 C16 H16A 108.3 . . ? O2 C17 O3 123.96(17) . . ? O2 C17 C16 125.63(15) . . ? O3 C17 C16 110.40(13) . . ? C17 O3 H3B 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 C15 N1 C1 C2 70.2(2) . . . . ? C14 N1 C1 C2 -114.11(18) . . . . ? C15 N1 C1 C6 -110.44(19) . . . . ? C14 N1 C1 C6 65.2(2) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? N1 C1 C2 C3 179.35(16) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? N1 C1 C6 C5 179.98(15) . . . . ? C2 C1 C6 C7 179.83(16) . . . . ? N1 C1 C6 C7 0.5(2) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 -179.58(17) . . . . ? C1 C6 C7 C8 -34.9(3) . . . . ? C5 C6 C7 C8 145.63(19) . . . . ? C6 C7 C8 C9 -1.8(3) . . . . ? C7 C8 C9 C14 34.5(3) . . . . ? C7 C8 C9 C10 -143.36(19) . . . . ? C14 C9 C10 C11 -2.5(3) . . . . ? C8 C9 C10 C11 175.50(18) . . . . ? C9 C10 C11 C12 0.6(3) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 C9 -1.6(3) . . . . ? C12 C13 C14 N1 179.00(16) . . . . ? C10 C9 C14 C13 2.9(3) . . . . ? C8 C9 C14 C13 -174.97(17) . . . . ? C10 C9 C14 N1 -177.65(16) . . . . ? C8 C9 C14 N1 4.5(3) . . . . ? C15 N1 C14 C13 -74.0(2) . . . . ? C1 N1 C14 C13 110.49(18) . . . . ? C15 N1 C14 C9 106.56(19) . . . . ? C1 N1 C14 C9 -69.0(2) . . . . ? C1 N1 C15 O1 -2.2(3) . . . . ? C14 N1 C15 O1 -177.52(16) . . . . ? C1 N1 C15 N2 176.55(16) . . . . ? C14 N1 C15 N2 1.2(3) . . . . ? C17 C16 C17 O2 121.79(19) 2_655 . . . ? C17 C16 C17 O3 -57.36(11) 2_655 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2C O2 0.88 2.31 3.026(2) 138.5 3_766 O3 H3B O1 0.84 1.74 2.5359(18) 158.6 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.423 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.044 # Attachment 'CBZ-SUA.cif' data_CBZ-SUA _database_code_depnum_ccdc_archive 'CCDC 671498' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cbzsua _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C17 H15 N2 O3' _chemical_formula_weight 295.31 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 17.536(2) _cell_length_b 5.1229(7) _cell_length_c 18.308(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.505(2) _cell_angle_gamma 90.00 _cell_volume 1445.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2295 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 24.96 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10666 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2544 _reflns_number_gt 2077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0448P)^2^+0.3898P] 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 2544 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 O1 O 0.72087(6) 0.1726(2) 0.55310(6) 0.0304(3) Uani 1 1 d . . . O2 O 0.39456(7) 0.3960(2) 0.39430(7) 0.0443(3) Uani 1 1 d . . . O3 O 0.25267(6) 0.4689(2) 0.34061(6) 0.0325(3) Uani 1 1 d . . . H3O H 0.2719(10) 0.603(3) 0.3859(10) 0.039 Uiso 1 1 d . . . N1 N 0.57482(8) 0.2001(3) 0.47715(7) 0.0337(3) Uani 1 1 d . . . H1A H 0.5709 0.2861 0.5168 0.040 Uiso 1 1 calc R . . H1B H 0.5277 0.1637 0.4305 0.040 Uiso 1 1 calc R . . N2 N 0.65626(7) -0.0102(2) 0.42531(7) 0.0265(3) Uani 1 1 d . . . C1 C 0.65240(9) 0.1248(3) 0.48780(8) 0.0256(3) Uani 1 1 d . . . C2 C 0.73953(9) -0.0769(3) 0.43296(8) 0.0264(3) Uani 1 1 d . . . C3 C 0.78725(9) -0.2792(3) 0.48501(9) 0.0314(4) Uani 1 1 d . . . H3A H 0.7648 -0.3739 0.5151 0.038 Uiso 1 1 calc R . . C4 C 0.86749(9) -0.3432(3) 0.49315(9) 0.0360(4) Uani 1 1 d . . . H4A H 0.9002 -0.4821 0.5287 0.043 Uiso 1 1 calc R . . C5 C 0.90008(10) -0.2041(3) 0.44925(10) 0.0397(4) Uani 1 1 d . . . H5A H 0.9551 -0.2480 0.4545 0.048 Uiso 1 1 calc R . . C6 C 0.85268(10) -0.0019(3) 0.39796(10) 0.0373(4) Uani 1 1 d . . . H6A H 0.8761 0.0936 0.3688 0.045 Uiso 1 1 calc R . . C7 C 0.77073(9) 0.0661(3) 0.38788(9) 0.0291(3) Uani 1 1 d . . . C8 C 0.72216(10) 0.2803(3) 0.33206(9) 0.0308(3) Uani 1 1 d . . . H8A H 0.7556 0.4208 0.3285 0.037 Uiso 1 1 calc R . . C9 C 0.63607(10) 0.3005(3) 0.28553(9) 0.0314(4) Uani 1 1 d . . . H9A H 0.6147 0.4558 0.2538 0.038 Uiso 1 1 calc R . . C10 C 0.57153(9) 0.1075(3) 0.27865(9) 0.0286(3) Uani 1 1 d . . . C11 C 0.49664(9) 0.0692(3) 0.20205(9) 0.0361(4) Uani 1 1 d . . . H11A H 0.4868 0.1774 0.1562 0.043 Uiso 1 1 calc R . . C12 C 0.43707(9) -0.1219(3) 0.19184(10) 0.0394(4) Uani 1 1 d . . . H12A H 0.3872 -0.1454 0.1393 0.047 Uiso 1 1 calc R . . C13 C 0.44985(9) -0.2799(3) 0.25821(10) 0.0373(4) Uani 1 1 d . . . H13A H 0.4090 -0.4128 0.2510 0.045 Uiso 1 1 calc R . . C14 C 0.52210(9) -0.2438(3) 0.33496(9) 0.0328(4) Uani 1 1 d . . . H14A H 0.5307 -0.3507 0.3807 0.039 Uiso 1 1 calc R . . C15 C 0.58201(9) -0.0506(3) 0.34499(8) 0.0270(3) Uani 1 1 d . . . C16 C 0.31985(9) 0.3407(3) 0.34505(9) 0.0288(3) Uani 1 1 d . . . C17 C 0.29647(9) 0.1185(3) 0.28489(9) 0.0327(4) Uani 1 1 d . . . H17A H 0.3071 -0.0472 0.3161 0.039 Uiso 1 1 calc R . . H17B H 0.3358 0.1221 0.2601 0.039 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 O1 0.0226(5) 0.0404(6) 0.0225(5) -0.0029(4) 0.0061(5) 0.0039(4) O2 0.0254(6) 0.0577(8) 0.0425(7) -0.0072(6) 0.0103(5) 0.0064(5) O3 0.0253(6) 0.0376(6) 0.0317(6) -0.0049(5) 0.0112(5) 0.0046(5) N1 0.0239(7) 0.0481(8) 0.0268(7) -0.0040(6) 0.0101(5) 0.0044(6) N2 0.0187(6) 0.0361(7) 0.0216(6) -0.0017(5) 0.0071(5) -0.0001(5) C1 0.0235(8) 0.0290(8) 0.0226(7) 0.0038(6) 0.0098(6) 0.0004(6) C2 0.0196(7) 0.0327(8) 0.0234(7) -0.0074(6) 0.0075(6) -0.0026(6) C3 0.0274(8) 0.0347(9) 0.0267(8) -0.0022(7) 0.0085(7) -0.0021(6) C4 0.0270(8) 0.0375(9) 0.0329(8) -0.0040(7) 0.0057(7) 0.0056(7) C5 0.0227(8) 0.0512(11) 0.0408(9) -0.0094(8) 0.0116(7) 0.0013(7) C6 0.0273(8) 0.0491(10) 0.0371(9) -0.0042(8) 0.0168(7) -0.0047(7) C7 0.0236(8) 0.0352(8) 0.0261(8) -0.0065(6) 0.0099(6) -0.0046(6) C8 0.0317(8) 0.0330(8) 0.0292(8) -0.0022(7) 0.0156(7) -0.0060(6) C9 0.0344(9) 0.0327(8) 0.0259(8) 0.0019(6) 0.0133(7) 0.0015(7) C10 0.0230(7) 0.0346(8) 0.0253(8) -0.0027(6) 0.0092(6) 0.0042(6) C11 0.0262(8) 0.0509(10) 0.0254(8) -0.0006(7) 0.0077(7) 0.0067(7) C12 0.0210(8) 0.0582(11) 0.0302(9) -0.0137(8) 0.0050(7) 0.0015(7) C13 0.0218(8) 0.0412(9) 0.0446(10) -0.0130(8) 0.0123(7) -0.0041(7) C14 0.0241(8) 0.0361(9) 0.0368(9) -0.0015(7) 0.0135(7) 0.0005(6) C15 0.0192(7) 0.0335(8) 0.0252(7) -0.0045(6) 0.0081(6) 0.0019(6) C16 0.0268(8) 0.0330(8) 0.0281(8) 0.0075(6) 0.0143(7) 0.0060(6) C17 0.0400(9) 0.0280(8) 0.0352(8) 0.0049(7) 0.0221(7) 0.0063(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 C1 1.2493(16) . ? O2 C16 1.2175(17) . ? O3 C16 1.3169(17) . ? O3 H3O 1.003(17) . ? N1 C1 1.3357(17) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C1 1.3660(18) . ? N2 C2 1.4399(17) . ? N2 C15 1.4399(17) . ? C2 C3 1.386(2) . ? C2 C7 1.396(2) . ? C3 C4 1.382(2) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4A 0.9500 . ? C5 C6 1.379(2) . ? C5 H5A 0.9500 . ? C6 C7 1.403(2) . ? C6 H6A 0.9500 . ? C7 C8 1.464(2) . ? C8 C9 1.337(2) . ? C8 H8A 0.9500 . ? C9 C10 1.462(2) . ? C9 H9A 0.9500 . ? C10 C15 1.397(2) . ? C10 C11 1.404(2) . ? C11 C12 1.378(2) . ? C11 H11A 0.9500 . ? C12 C13 1.386(2) . ? C12 H12A 0.9500 . ? C13 C14 1.384(2) . ? C13 H13A 0.9500 . ? C14 C15 1.390(2) . ? C14 H14A 0.9500 . ? C16 C17 1.499(2) . ? C17 C17 1.517(3) 2 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? 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 O3 H3O 110.6(9) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 C2 119.48(11) . . ? C1 N2 C15 123.10(11) . . ? C2 N2 C15 116.49(11) . . ? O1 C1 N1 122.00(13) . . ? O1 C1 N2 119.44(12) . . ? N1 C1 N2 118.56(12) . . ? C3 C2 C7 121.37(13) . . ? C3 C2 N2 119.73(13) . . ? C7 C2 N2 118.89(13) . . ? C4 C3 C2 120.08(14) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 119.73(15) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C6 C5 C4 120.02(14) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C7 121.54(15) . . ? C5 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C2 C7 C6 117.24(14) . . ? C2 C7 C8 122.99(13) . . ? C6 C7 C8 119.76(14) . . ? C9 C8 C7 127.36(14) . . ? C9 C8 H8A 116.3 . . ? C7 C8 H8A 116.3 . . ? C8 C9 C10 126.47(14) . . ? C8 C9 H9A 116.8 . . ? C10 C9 H9A 116.8 . . ? C15 C10 C11 117.33(14) . . ? C15 C10 C9 122.81(13) . . ? C11 C10 C9 119.82(14) . . ? C12 C11 C10 121.48(15) . . ? C12 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? C11 C12 C13 120.07(14) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C14 C13 C12 119.90(15) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 119.83(15) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C14 C15 C10 121.36(13) . . ? C14 C15 N2 119.70(13) . . ? C10 C15 N2 118.94(12) . . ? O2 C16 O3 122.99(14) . . ? O2 C16 C17 122.78(13) . . ? O3 C16 C17 114.23(13) . . ? C16 C17 C17 115.22(11) . 2 ? C16 C17 H17A 108.5 . . ? C17 C17 H17A 108.5 2 . ? C16 C17 H17B 108.5 . . ? C17 C17 H17B 108.5 2 . ? H17A C17 H17B 107.5 . . ? 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 N2 C1 O1 -4.9(2) . . . . ? C15 N2 C1 O1 -173.47(13) . . . . ? C2 N2 C1 N1 175.59(13) . . . . ? C15 N2 C1 N1 7.0(2) . . . . ? C1 N2 C2 C3 75.72(17) . . . . ? C15 N2 C2 C3 -114.99(15) . . . . ? C1 N2 C2 C7 -103.80(15) . . . . ? C15 N2 C2 C7 65.48(17) . . . . ? C7 C2 C3 C4 0.0(2) . . . . ? N2 C2 C3 C4 -179.54(13) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C7 -0.9(2) . . . . ? C3 C2 C7 C6 -0.5(2) . . . . ? N2 C2 C7 C6 179.00(13) . . . . ? C3 C2 C7 C8 179.75(13) . . . . ? N2 C2 C7 C8 -0.7(2) . . . . ? C5 C6 C7 C2 1.0(2) . . . . ? C5 C6 C7 C8 -179.30(14) . . . . ? C2 C7 C8 C9 -33.6(2) . . . . ? C6 C7 C8 C9 146.62(16) . . . . ? C7 C8 C9 C10 -1.9(2) . . . . ? C8 C9 C10 C15 33.9(2) . . . . ? C8 C9 C10 C11 -143.83(15) . . . . ? C15 C10 C11 C12 -1.9(2) . . . . ? C9 C10 C11 C12 175.91(14) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C10 -0.8(2) . . . . ? C13 C14 C15 N2 178.81(13) . . . . ? C11 C10 C15 C14 2.0(2) . . . . ? C9 C10 C15 C14 -175.79(14) . . . . ? C11 C10 C15 N2 -177.60(12) . . . . ? C9 C10 C15 N2 4.6(2) . . . . ? C1 N2 C15 C14 -79.23(18) . . . . ? C2 N2 C15 C14 111.91(15) . . . . ? C1 N2 C15 C10 100.36(16) . . . . ? C2 N2 C15 C10 -68.50(17) . . . . ? O2 C16 C17 C17 -165.68(15) . . . 2 ? O3 C16 C17 C17 15.00(19) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O O1 1.003(17) 1.566(17) 2.5522(14) 166.7(14) 3_666 N1 H1A O2 0.88 2.17 2.9837(17) 152.7 3_666 N1 H1B O2 0.88 2.41 2.9536(16) 119.9 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.160 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.034 # Attachment 'SFZ-SAC.cif' data_SFZ-SAC _database_code_depnum_ccdc_archive 'CCDC 671499' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common sfzsac _chemical_melting_point 155C _chemical_formula_moiety 'C12 H15 N4 O2 S, C7 H4 N O3 S' _chemical_formula_sum 'C19 H19 N5 O5 S2' _chemical_formula_weight 461.51 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 'Pbca ' 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' '-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 10.5106(13) _cell_length_b 16.035(2) _cell_length_c 25.247(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4255.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2889 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.47 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8920 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details 'E.Lu / Prof. R. Sury' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48432 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4878 _reflns_number_gt 3749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0564P)^2^+1.7859P] 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 4878 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _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 0.57719(5) 0.19803(3) 0.66469(2) 0.03645(15) Uani 1 1 d . . . O1 O 0.50915(17) 0.15757(9) 0.70637(6) 0.0481(4) Uani 1 1 d . . . O2 O 0.70175(15) 0.16884(10) 0.65103(6) 0.0474(4) Uani 1 1 d . . . N1 N 0.49975(16) 0.18473(11) 0.60819(6) 0.0335(4) Uani 1 1 d . . . H1A H 0.5442 0.1675 0.5808 0.040 Uiso 1 1 calc R . . N2 N 0.30239(17) 0.23156(10) 0.63838(7) 0.0339(4) Uani 1 1 d . . . N3 N 0.32605(15) 0.17569(9) 0.55292(6) 0.0277(3) Uani 1 1 d . . . H3A H 0.3768 0.1525 0.5294 0.033 Uiso 1 1 calc R . . N4 N 0.6133(2) 0.55746(12) 0.70914(8) 0.0516(5) Uani 1 1 d . . . H4A H 0.5580 0.5819 0.7302 0.062 Uiso 1 1 calc R . . H4B H 0.6744 0.5869 0.6943 0.062 Uiso 1 1 calc R . . C1 C 0.37276(19) 0.19830(11) 0.60053(7) 0.0290(4) Uani 1 1 d . . . C2 C 0.1784(2) 0.24222(12) 0.62788(8) 0.0352(5) Uani 1 1 d . . . C3 C 0.1254(2) 0.22175(12) 0.57925(8) 0.0332(4) Uani 1 1 d . . . H3B H 0.0375 0.2308 0.5727 0.040 Uiso 1 1 calc R . . C4 C 0.20231(18) 0.18823(11) 0.54085(8) 0.0286(4) Uani 1 1 d . . . C5 C 0.0995(2) 0.27640(16) 0.67227(9) 0.0490(6) Uani 1 1 d . . . H5A H 0.1432 0.3243 0.6882 0.074 Uiso 1 1 calc R . . H5B H 0.0871 0.2331 0.6992 0.074 Uiso 1 1 calc R . . H5C H 0.0167 0.2942 0.6585 0.074 Uiso 1 1 calc R . . C6 C 0.1607(2) 0.16561(13) 0.48645(8) 0.0339(4) Uani 1 1 d . . . H6A H 0.1870 0.1083 0.4786 0.051 Uiso 1 1 calc R . . H6B H 0.1997 0.2038 0.4609 0.051 Uiso 1 1 calc R . . H6C H 0.0678 0.1698 0.4841 0.051 Uiso 1 1 calc R . . C7 C 0.5844(2) 0.30409(12) 0.67770(8) 0.0321(4) Uani 1 1 d . . . C8 C 0.4967(2) 0.34233(13) 0.71130(8) 0.0339(4) Uani 1 1 d . . . H8A H 0.4292 0.3107 0.7263 0.041 Uiso 1 1 calc R . . C9 C 0.5081(2) 0.42594(13) 0.72274(8) 0.0352(5) Uani 1 1 d . . . H9A H 0.4500 0.4513 0.7466 0.042 Uiso 1 1 calc R . . C10 C 0.6045(2) 0.47415(13) 0.69955(8) 0.0367(5) Uani 1 1 d . . . C11 C 0.6915(2) 0.43489(14) 0.66549(8) 0.0389(5) Uani 1 1 d . . . H11A H 0.7574 0.4667 0.6495 0.047 Uiso 1 1 calc R . . C12 C 0.6824(2) 0.35110(14) 0.65500(8) 0.0380(5) Uani 1 1 d . . . H12A H 0.7426 0.3250 0.6323 0.046 Uiso 1 1 calc R . . S2 S 0.78399(5) 0.09637(3) 0.51752(2) 0.03100(14) Uani 1 1 d . . . O3 O 0.82633(15) 0.03610(9) 0.55551(6) 0.0403(4) Uani 1 1 d . . . O4 O 0.85480(14) 0.17301(9) 0.51539(6) 0.0401(4) Uani 1 1 d . . . O5 O 0.44996(13) 0.10212(9) 0.47570(6) 0.0367(3) Uani 1 1 d . . . N5 N 0.63309(15) 0.11613(10) 0.52390(7) 0.0312(4) Uani 1 1 d . . . C13 C 0.56734(18) 0.09229(12) 0.48092(8) 0.0291(4) Uani 1 1 d . . . C14 C 0.64642(19) 0.05284(11) 0.43896(8) 0.0294(4) Uani 1 1 d . . . C15 C 0.6084(2) 0.02058(13) 0.39066(8) 0.0364(5) Uani 1 1 d . . . H15A H 0.5216 0.0219 0.3802 0.044 Uiso 1 1 calc R . . C16 C 0.7011(2) -0.01382(13) 0.35793(9) 0.0404(5) Uani 1 1 d . . . H16A H 0.6774 -0.0361 0.3245 0.048 Uiso 1 1 calc R . . C17 C 0.8275(2) -0.01605(13) 0.37344(9) 0.0407(5) Uani 1 1 d . . . H17A H 0.8888 -0.0405 0.3506 0.049 Uiso 1 1 calc R . . C18 C 0.8667(2) 0.01682(13) 0.42191(9) 0.0374(5) Uani 1 1 d . . . H18A H 0.9534 0.0157 0.4326 0.045 Uiso 1 1 calc R . . C19 C 0.77332(19) 0.05104(12) 0.45361(8) 0.0308(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0418(3) 0.0334(3) 0.0341(3) 0.0002(2) -0.0084(2) 0.0027(2) O1 0.0703(12) 0.0372(8) 0.0368(8) 0.0075(7) -0.0060(8) -0.0055(8) O2 0.0424(9) 0.0450(9) 0.0547(10) -0.0071(7) -0.0155(8) 0.0138(7) N1 0.0313(9) 0.0398(10) 0.0293(8) -0.0054(7) -0.0014(7) 0.0017(7) N2 0.0389(10) 0.0327(9) 0.0300(9) -0.0028(7) 0.0056(8) -0.0002(8) N3 0.0288(8) 0.0273(8) 0.0271(8) -0.0014(6) 0.0032(7) 0.0012(7) N4 0.0620(14) 0.0376(11) 0.0552(12) -0.0036(9) 0.0148(10) -0.0098(10) C1 0.0331(10) 0.0241(9) 0.0298(10) 0.0010(8) 0.0016(8) -0.0011(8) C2 0.0384(11) 0.0301(10) 0.0371(11) 0.0007(8) 0.0084(9) 0.0015(9) C3 0.0305(11) 0.0302(10) 0.0388(11) -0.0006(8) 0.0036(9) 0.0017(8) C4 0.0272(10) 0.0236(9) 0.0351(10) 0.0026(8) 0.0007(8) -0.0003(8) C5 0.0507(15) 0.0540(14) 0.0423(13) -0.0051(11) 0.0138(11) 0.0089(12) C6 0.0289(10) 0.0335(10) 0.0393(11) -0.0027(9) -0.0019(9) 0.0015(9) C7 0.0360(11) 0.0327(10) 0.0277(10) 0.0001(8) -0.0052(8) 0.0006(9) C8 0.0372(11) 0.0361(11) 0.0282(10) 0.0058(9) -0.0034(8) -0.0020(9) C9 0.0394(12) 0.0372(11) 0.0291(10) 0.0009(8) 0.0001(9) 0.0011(9) C10 0.0435(12) 0.0362(11) 0.0303(10) 0.0005(8) -0.0039(9) -0.0031(9) C11 0.0395(12) 0.0432(12) 0.0340(11) 0.0015(9) 0.0021(9) -0.0073(10) C12 0.0381(12) 0.0460(12) 0.0298(11) -0.0029(9) -0.0001(9) 0.0008(10) S2 0.0251(2) 0.0292(3) 0.0387(3) -0.0001(2) -0.0008(2) 0.0021(2) O3 0.0415(9) 0.0384(8) 0.0411(8) 0.0044(7) -0.0051(7) 0.0079(7) O4 0.0279(8) 0.0335(8) 0.0589(10) -0.0010(7) -0.0033(7) -0.0030(6) O5 0.0245(7) 0.0440(8) 0.0415(8) -0.0076(7) 0.0011(6) 0.0014(6) N5 0.0240(8) 0.0326(9) 0.0369(9) -0.0026(7) 0.0014(7) 0.0008(7) C13 0.0258(10) 0.0261(9) 0.0355(10) -0.0009(8) 0.0021(8) -0.0015(8) C14 0.0288(10) 0.0252(10) 0.0342(10) 0.0014(8) 0.0037(8) 0.0004(8) C15 0.0391(12) 0.0341(11) 0.0360(11) 0.0007(9) 0.0015(9) -0.0008(9) C16 0.0531(14) 0.0345(11) 0.0337(11) -0.0002(9) 0.0076(10) -0.0022(10) C17 0.0461(13) 0.0329(11) 0.0431(12) 0.0024(9) 0.0190(10) 0.0043(10) C18 0.0316(11) 0.0329(11) 0.0476(13) 0.0065(9) 0.0104(10) 0.0032(9) C19 0.0308(11) 0.0252(9) 0.0365(11) 0.0038(8) 0.0048(8) 0.0010(8) _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 O1 1.4281(16) . ? S1 O2 1.4325(17) . ? S1 N1 1.6562(17) . ? S1 C7 1.734(2) . ? N1 C1 1.366(3) . ? N1 H1A 0.8800 . ? N2 C1 1.321(2) . ? N2 C2 1.340(3) . ? N3 C1 1.348(2) . ? N3 C4 1.351(2) . ? N3 H3A 0.8800 . ? N4 C10 1.361(3) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C2 C3 1.388(3) . ? C2 C5 1.498(3) . ? C3 C4 1.372(3) . ? C3 H3B 0.9500 . ? C4 C6 1.486(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.394(3) . ? C7 C12 1.400(3) . ? C8 C9 1.377(3) . ? C8 H8A 0.9500 . ? C9 C10 1.402(3) . ? C9 H9A 0.9500 . ? C10 C11 1.404(3) . ? C11 C12 1.373(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? S2 O3 1.4325(15) . ? S2 O4 1.4376(15) . ? S2 N5 1.6255(17) . ? S2 C19 1.773(2) . ? O5 C13 1.251(2) . ? N5 C13 1.342(3) . ? C13 C14 1.488(3) . ? C14 C15 1.384(3) . ? C14 C19 1.384(3) . ? C15 C16 1.392(3) . ? C15 H15A 0.9500 . ? C16 C17 1.386(3) . ? C16 H16A 0.9500 . ? C17 C18 1.395(3) . ? C17 H17A 0.9500 . ? C18 C19 1.380(3) . ? C18 H18A 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 O1 S1 O2 119.12(10) . . ? O1 S1 N1 109.27(10) . . ? O2 S1 N1 101.52(9) . . ? O1 S1 C7 109.14(10) . . ? O2 S1 C7 109.05(10) . . ? N1 S1 C7 108.11(9) . . ? C1 N1 S1 125.57(14) . . ? C1 N1 H1A 117.2 . . ? S1 N1 H1A 117.2 . . ? C1 N2 C2 116.92(18) . . ? C1 N3 C4 120.77(17) . . ? C1 N3 H3A 119.6 . . ? C4 N3 H3A 119.6 . . ? C10 N4 H4A 120.0 . . ? C10 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N2 C1 N3 123.35(19) . . ? N2 C1 N1 120.59(18) . . ? N3 C1 N1 116.05(17) . . ? N2 C2 C3 122.35(19) . . ? N2 C2 C5 115.9(2) . . ? C3 C2 C5 121.7(2) . . ? C4 C3 C2 118.78(19) . . ? C4 C3 H3B 120.6 . . ? C2 C3 H3B 120.6 . . ? N3 C4 C3 117.78(18) . . ? N3 C4 C6 117.11(17) . . ? C3 C4 C6 125.11(18) . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 119.92(19) . . ? C8 C7 S1 121.19(16) . . ? C12 C7 S1 118.86(16) . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? N4 C10 C9 121.1(2) . . ? N4 C10 C11 120.3(2) . . ? C9 C10 C11 118.6(2) . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C7 120.0(2) . . ? C11 C12 H12A 120.0 . . ? C7 C12 H12A 120.0 . . ? O3 S2 O4 116.16(9) . . ? O3 S2 N5 111.60(9) . . ? O4 S2 N5 110.01(9) . . ? O3 S2 C19 110.63(9) . . ? O4 S2 C19 110.44(9) . . ? N5 S2 C19 96.22(9) . . ? C13 N5 S2 111.52(13) . . ? O5 C13 N5 123.87(18) . . ? O5 C13 C14 121.98(18) . . ? N5 C13 C14 114.15(17) . . ? C15 C14 C19 120.41(19) . . ? C15 C14 C13 128.68(19) . . ? C19 C14 C13 110.91(17) . . ? C14 C15 C16 118.0(2) . . ? C14 C15 H15A 121.0 . . ? C16 C15 H15A 121.0 . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? C16 C17 C18 121.4(2) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C19 C18 C17 116.7(2) . . ? C19 C18 H18A 121.7 . . ? C17 C18 H18A 121.7 . . ? C18 C19 C14 122.6(2) . . ? C18 C19 S2 130.20(17) . . ? C14 C19 S2 107.19(14) . . ? 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 O1 S1 N1 C1 48.93(19) . . . . ? O2 S1 N1 C1 175.61(17) . . . . ? C7 S1 N1 C1 -69.74(19) . . . . ? C2 N2 C1 N3 0.4(3) . . . . ? C2 N2 C1 N1 -179.48(18) . . . . ? C4 N3 C1 N2 1.7(3) . . . . ? C4 N3 C1 N1 -178.44(16) . . . . ? S1 N1 C1 N2 6.3(3) . . . . ? S1 N1 C1 N3 -173.54(13) . . . . ? C1 N2 C2 C3 -1.7(3) . . . . ? C1 N2 C2 C5 177.31(18) . . . . ? N2 C2 C3 C4 1.0(3) . . . . ? C5 C2 C3 C4 -177.9(2) . . . . ? C1 N3 C4 C3 -2.3(3) . . . . ? C1 N3 C4 C6 176.78(17) . . . . ? C2 C3 C4 N3 1.0(3) . . . . ? C2 C3 C4 C6 -178.03(18) . . . . ? O1 S1 C7 C8 -22.0(2) . . . . ? O2 S1 C7 C8 -153.71(16) . . . . ? N1 S1 C7 C8 96.70(17) . . . . ? O1 S1 C7 C12 156.18(16) . . . . ? O2 S1 C7 C12 24.52(19) . . . . ? N1 S1 C7 C12 -85.07(18) . . . . ? C12 C7 C8 C9 -1.1(3) . . . . ? S1 C7 C8 C9 177.13(15) . . . . ? C7 C8 C9 C10 2.2(3) . . . . ? C8 C9 C10 N4 177.5(2) . . . . ? C8 C9 C10 C11 -1.8(3) . . . . ? N4 C10 C11 C12 -179.1(2) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C7 1.0(3) . . . . ? C8 C7 C12 C11 -0.5(3) . . . . ? S1 C7 C12 C11 -178.79(16) . . . . ? O3 S2 N5 C13 -115.63(14) . . . . ? O4 S2 N5 C13 113.92(14) . . . . ? C19 S2 N5 C13 -0.52(15) . . . . ? S2 N5 C13 O5 -178.65(16) . . . . ? S2 N5 C13 C14 1.1(2) . . . . ? O5 C13 C14 C15 -1.4(3) . . . . ? N5 C13 C14 C15 178.92(19) . . . . ? O5 C13 C14 C19 178.51(18) . . . . ? N5 C13 C14 C19 -1.2(2) . . . . ? C19 C14 C15 C16 0.4(3) . . . . ? C13 C14 C15 C16 -179.69(19) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C18 -0.8(3) . . . . ? C16 C17 C18 C19 0.4(3) . . . . ? C17 C18 C19 C14 0.4(3) . . . . ? C17 C18 C19 S2 178.56(16) . . . . ? C15 C14 C19 C18 -0.8(3) . . . . ? C13 C14 C19 C18 179.28(18) . . . . ? C15 C14 C19 S2 -179.36(15) . . . . ? C13 C14 C19 S2 0.75(19) . . . . ? O3 S2 C19 C18 -62.7(2) . . . . ? O4 S2 C19 C18 67.4(2) . . . . ? N5 S2 C19 C18 -178.56(19) . . . . ? O3 S2 C19 C14 115.72(14) . . . . ? O4 S2 C19 C14 -114.26(14) . . . . ? N5 S2 C19 C14 -0.18(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N5 0.88 1.90 2.775(2) 172.6 . N3 H3A O5 0.88 1.76 2.625(2) 168.6 . N4 H4A O1 0.88 2.13 2.964(3) 158.0 3_656 N4 H4B O2 0.88 2.15 3.020(3) 170.5 8_765 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.265 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.049 # Attachment 'TPL-SAC.cif' data_TPL-SAC _database_code_depnum_ccdc_archive 'CCDC 671500' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common tplsac _chemical_melting_point 207C _chemical_formula_moiety 'C7 H8 N4 O2, C7 H5 N O3 S' _chemical_formula_sum 'C14 H13 N5 O5 S' _chemical_formula_weight 363.35 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 8.7638(11) _cell_length_b 8.7638(11) _cell_length_c 11.5480(14) _cell_angle_alpha 71.823(2) _cell_angle_beta 75.951(2) _cell_angle_gamma 64.113(2) _cell_volume 752.20(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.45 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8828 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details 'E. Lu / Prof. R. Sury' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8831 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3390 _reflns_number_gt 2883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0719P)^2^+0.1711P] 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 3390 _refine_ls_number_parameters 234 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 O1A O 0.41910(16) 0.87989(17) 0.33806(12) 0.0276(3) Uani 1 1 d . . . O2A O 0.71360(17) 1.16883(17) 0.03834(12) 0.0288(3) Uani 1 1 d . . . N1A N 0.7392(2) 0.6340(2) 0.01074(14) 0.0249(3) Uani 1 1 d . . . N2A N 0.5647(2) 0.60362(19) 0.18569(14) 0.0230(3) Uani 1 1 d D . . H2AA H 0.506(2) 0.557(3) 0.2481(12) 0.028 Uiso 1 1 d D . . N3A N 0.55837(18) 1.02857(18) 0.18278(13) 0.0207(3) Uani 1 1 d . . . N4A N 0.73442(19) 0.91296(19) 0.01384(13) 0.0219(3) Uani 1 1 d . . . C1A C 0.6614(2) 0.5348(2) 0.09081(16) 0.0260(4) Uani 1 1 d . . . H1AA H 0.6735 0.4260 0.0814 0.031 Uiso 1 1 calc R . . C2A C 0.5789(2) 0.7599(2) 0.16716(15) 0.0202(3) Uani 1 1 d . . . C3A C 0.5099(2) 0.8861(2) 0.23844(16) 0.0198(3) Uani 1 1 d . . . C4A C 0.6718(2) 1.0440(2) 0.07552(16) 0.0210(3) Uani 1 1 d . . . C5A C 0.6866(2) 0.7732(2) 0.06001(15) 0.0202(3) Uani 1 1 d . . . C6A C 0.4929(2) 1.1707(2) 0.24675(18) 0.0280(4) Uani 1 1 d . . . H6AA H 0.4427 1.2829 0.1891 0.042 Uiso 1 1 calc R . . H6AB H 0.5871 1.1698 0.2790 0.042 Uiso 1 1 calc R . . H6AC H 0.4055 1.1539 0.3148 0.042 Uiso 1 1 calc R . . C7A C 0.8604(3) 0.9184(3) -0.09593(18) 0.0329(4) Uani 1 1 d . . . H7AA H 0.9605 0.9217 -0.0747 0.049 Uiso 1 1 calc R . . H7AB H 0.8093 1.0230 -0.1595 0.049 Uiso 1 1 calc R . . H7AC H 0.8955 0.8142 -0.1268 0.049 Uiso 1 1 calc R . . S1B S 0.08615(5) 0.74919(5) 0.61119(4) 0.02058(14) Uani 1 1 d . . . O1B O 0.16491(17) 0.78232(18) 0.69054(12) 0.0302(3) Uani 1 1 d . . . O2B O -0.07661(16) 0.87763(16) 0.57822(12) 0.0293(3) Uani 1 1 d . . . O3B O 0.37422(17) 0.47056(17) 0.39358(12) 0.0310(3) Uani 1 1 d . . . N1B N 0.22419(19) 0.6989(2) 0.48834(14) 0.0236(3) Uani 1 1 d D . . H1BA H 0.281(2) 0.764(2) 0.4436(16) 0.028 Uiso 1 1 d D . . C1B C 0.2724(2) 0.5323(2) 0.47571(16) 0.0216(4) Uani 1 1 d . . . C2B C 0.1788(2) 0.4412(2) 0.57748(15) 0.0196(3) Uani 1 1 d . . . C3B C 0.1838(2) 0.2759(2) 0.59339(16) 0.0235(4) Uani 1 1 d . . . H3BA H 0.2542 0.2055 0.5374 0.028 Uiso 1 1 calc R . . C4B C 0.0822(2) 0.2157(2) 0.69426(17) 0.0253(4) Uani 1 1 d . . . H4BA H 0.0813 0.1039 0.7060 0.030 Uiso 1 1 calc R . . C5B C -0.0177(2) 0.3176(2) 0.77778(17) 0.0259(4) Uani 1 1 d . . . H5BA H -0.0842 0.2731 0.8466 0.031 Uiso 1 1 calc R . . C6B C -0.0222(2) 0.4838(2) 0.76245(16) 0.0235(4) Uani 1 1 d . . . H6BA H -0.0905 0.5540 0.8190 0.028 Uiso 1 1 calc R . . C7B C 0.0775(2) 0.5415(2) 0.66093(15) 0.0195(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0281(7) 0.0288(7) 0.0273(7) -0.0117(5) 0.0079(5) -0.0150(6) O2A 0.0331(7) 0.0266(7) 0.0311(7) -0.0079(6) 0.0017(6) -0.0178(6) N1A 0.0283(8) 0.0231(7) 0.0243(8) -0.0095(6) 0.0006(6) -0.0104(6) N2A 0.0266(8) 0.0198(7) 0.0233(7) -0.0057(6) 0.0008(6) -0.0113(6) N3A 0.0202(7) 0.0194(7) 0.0235(7) -0.0072(6) -0.0004(6) -0.0083(6) N4A 0.0241(7) 0.0230(7) 0.0200(7) -0.0060(6) 0.0019(6) -0.0122(6) C1A 0.0301(9) 0.0227(9) 0.0260(9) -0.0088(7) -0.0007(7) -0.0106(7) C2A 0.0192(8) 0.0196(8) 0.0219(8) -0.0049(6) -0.0020(6) -0.0080(6) C3A 0.0158(7) 0.0201(8) 0.0228(8) -0.0049(7) -0.0028(6) -0.0064(6) C4A 0.0190(8) 0.0214(8) 0.0229(8) -0.0041(7) -0.0044(6) -0.0083(7) C5A 0.0194(8) 0.0205(8) 0.0206(8) -0.0043(6) -0.0036(6) -0.0073(6) C6A 0.0288(9) 0.0243(9) 0.0331(10) -0.0137(8) 0.0023(8) -0.0108(8) C7A 0.0372(11) 0.0389(11) 0.0270(10) -0.0125(8) 0.0108(8) -0.0232(9) S1B 0.0212(2) 0.0193(2) 0.0222(2) -0.00655(16) 0.00018(16) -0.00924(17) O1B 0.0353(8) 0.0329(7) 0.0309(7) -0.0119(6) -0.0043(6) -0.0180(6) O2B 0.0228(7) 0.0217(6) 0.0388(8) -0.0069(6) -0.0028(6) -0.0053(5) O3B 0.0334(8) 0.0308(7) 0.0271(7) -0.0124(6) 0.0086(6) -0.0137(6) N1B 0.0248(8) 0.0234(7) 0.0238(7) -0.0067(6) 0.0044(6) -0.0137(6) C1B 0.0206(8) 0.0222(8) 0.0228(8) -0.0062(7) -0.0016(7) -0.0089(7) C2B 0.0167(8) 0.0216(8) 0.0200(8) -0.0046(6) -0.0032(6) -0.0069(6) C3B 0.0231(8) 0.0221(8) 0.0262(9) -0.0073(7) -0.0048(7) -0.0077(7) C4B 0.0275(9) 0.0219(8) 0.0291(9) -0.0033(7) -0.0063(7) -0.0126(7) C5B 0.0248(9) 0.0284(9) 0.0250(9) -0.0028(7) -0.0011(7) -0.0140(8) C6B 0.0213(8) 0.0254(9) 0.0232(8) -0.0077(7) 0.0008(7) -0.0092(7) C7B 0.0187(8) 0.0183(8) 0.0219(8) -0.0036(6) -0.0038(6) -0.0077(6) _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 O1A C3A 1.231(2) . ? O2A C4A 1.223(2) . ? N1A C1A 1.337(2) . ? N1A C5A 1.356(2) . ? N2A C1A 1.341(2) . ? N2A C2A 1.375(2) . ? N2A H2AA 0.878(5) . ? N3A C4A 1.399(2) . ? N3A C3A 1.408(2) . ? N3A C6A 1.473(2) . ? N4A C5A 1.376(2) . ? N4A C4A 1.378(2) . ? N4A C7A 1.469(2) . ? C1A H1AA 0.9500 . ? C2A C5A 1.369(2) . ? C2A C3A 1.417(2) . ? C6A H6AA 0.9800 . ? C6A H6AB 0.9800 . ? C6A H6AC 0.9800 . ? C7A H7AA 0.9800 . ? C7A H7AB 0.9800 . ? C7A H7AC 0.9800 . ? S1B O2B 1.4286(13) . ? S1B O1B 1.4312(13) . ? S1B N1B 1.6618(15) . ? S1B C7B 1.7595(17) . ? O3B C1B 1.215(2) . ? N1B C1B 1.378(2) . ? N1B H1BA 0.881(5) . ? C1B C2B 1.487(2) . ? C2B C3B 1.384(2) . ? C2B C7B 1.386(2) . ? C3B C4B 1.397(3) . ? C3B H3BA 0.9500 . ? C4B C5B 1.393(3) . ? C4B H4BA 0.9500 . ? C5B C6B 1.395(2) . ? C5B H5BA 0.9500 . ? C6B C7B 1.383(2) . ? C6B H6BA 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 C1A N1A C5A 103.02(15) . . ? C1A N2A C2A 106.32(15) . . ? C1A N2A H2AA 126.7(14) . . ? C2A N2A H2AA 126.9(14) . . ? C4A N3A C3A 126.16(14) . . ? C4A N3A C6A 116.18(14) . . ? C3A N3A C6A 117.54(15) . . ? C5A N4A C4A 119.68(14) . . ? C5A N4A C7A 120.72(15) . . ? C4A N4A C7A 119.47(15) . . ? N1A C1A N2A 113.45(16) . . ? N1A C1A H1AA 123.3 . . ? N2A C1A H1AA 123.3 . . ? C5A C2A N2A 105.05(15) . . ? C5A C2A C3A 123.20(16) . . ? N2A C2A C3A 131.70(16) . . ? O1A C3A N3A 120.81(15) . . ? O1A C3A C2A 127.15(16) . . ? N3A C3A C2A 112.04(15) . . ? O2A C4A N4A 121.52(16) . . ? O2A C4A N3A 121.20(15) . . ? N4A C4A N3A 117.27(14) . . ? N1A C5A C2A 112.16(15) . . ? N1A C5A N4A 126.34(16) . . ? C2A C5A N4A 121.48(15) . . ? N3A C6A H6AA 109.5 . . ? N3A C6A H6AB 109.5 . . ? H6AA C6A H6AB 109.5 . . ? N3A C6A H6AC 109.5 . . ? H6AA C6A H6AC 109.5 . . ? H6AB C6A H6AC 109.5 . . ? N4A C7A H7AA 109.5 . . ? N4A C7A H7AB 109.5 . . ? H7AA C7A H7AB 109.5 . . ? N4A C7A H7AC 109.5 . . ? H7AA C7A H7AC 109.5 . . ? H7AB C7A H7AC 109.5 . . ? O2B S1B O1B 117.43(8) . . ? O2B S1B N1B 111.72(8) . . ? O1B S1B N1B 109.54(8) . . ? O2B S1B C7B 109.46(8) . . ? O1B S1B C7B 113.43(8) . . ? N1B S1B C7B 92.55(8) . . ? C1B N1B S1B 115.53(12) . . ? C1B N1B H1BA 120.8(14) . . ? S1B N1B H1BA 122.3(14) . . ? O3B C1B N1B 125.17(16) . . ? O3B C1B C2B 125.59(16) . . ? N1B C1B C2B 109.24(14) . . ? C3B C2B C7B 120.42(16) . . ? C3B C2B C1B 127.03(16) . . ? C7B C2B C1B 112.54(15) . . ? C2B C3B C4B 118.02(16) . . ? C2B C3B H3BA 121.0 . . ? C4B C3B H3BA 121.0 . . ? C5B C4B C3B 120.82(17) . . ? C5B C4B H4BA 119.6 . . ? C3B C4B H4BA 119.6 . . ? C4B C5B C6B 121.30(17) . . ? C4B C5B H5BA 119.3 . . ? C6B C5B H5BA 119.3 . . ? C7B C6B C5B 116.79(16) . . ? C7B C6B H6BA 121.6 . . ? C5B C6B H6BA 121.6 . . ? C6B C7B C2B 122.64(16) . . ? C6B C7B S1B 127.20(13) . . ? C2B C7B S1B 110.02(13) . . ? 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 C5A N1A C1A N2A 0.0(2) . . . . ? C2A N2A C1A N1A 0.2(2) . . . . ? C1A N2A C2A C5A -0.31(19) . . . . ? C1A N2A C2A C3A -177.86(18) . . . . ? C4A N3A C3A O1A 174.38(15) . . . . ? C6A N3A C3A O1A -1.4(2) . . . . ? C4A N3A C3A C2A -5.1(2) . . . . ? C6A N3A C3A C2A 179.11(14) . . . . ? C5A C2A C3A O1A -176.40(17) . . . . ? N2A C2A C3A O1A 0.8(3) . . . . ? C5A C2A C3A N3A 3.0(2) . . . . ? N2A C2A C3A N3A -179.83(17) . . . . ? C5A N4A C4A O2A 178.81(16) . . . . ? C7A N4A C4A O2A 2.9(3) . . . . ? C5A N4A C4A N3A -1.1(2) . . . . ? C7A N4A C4A N3A -177.01(16) . . . . ? C3A N3A C4A O2A -175.61(16) . . . . ? C6A N3A C4A O2A 0.3(2) . . . . ? C3A N3A C4A N4A 4.3(2) . . . . ? C6A N3A C4A N4A -179.83(15) . . . . ? C1A N1A C5A C2A -0.2(2) . . . . ? C1A N1A C5A N4A 178.25(16) . . . . ? N2A C2A C5A N1A 0.3(2) . . . . ? C3A C2A C5A N1A 178.15(16) . . . . ? N2A C2A C5A N4A -178.21(15) . . . . ? C3A C2A C5A N4A -0.4(3) . . . . ? C4A N4A C5A N1A -179.02(16) . . . . ? C7A N4A C5A N1A -3.2(3) . . . . ? C4A N4A C5A C2A -0.7(2) . . . . ? C7A N4A C5A C2A 175.18(17) . . . . ? O2B S1B N1B C1B -112.30(13) . . . . ? O1B S1B N1B C1B 115.82(13) . . . . ? C7B S1B N1B C1B -0.17(14) . . . . ? S1B N1B C1B O3B -178.47(15) . . . . ? S1B N1B C1B C2B 2.12(18) . . . . ? O3B C1B C2B C3B -3.6(3) . . . . ? N1B C1B C2B C3B 175.83(16) . . . . ? O3B C1B C2B C7B 176.97(17) . . . . ? N1B C1B C2B C7B -3.6(2) . . . . ? C7B C2B C3B C4B 1.0(2) . . . . ? C1B C2B C3B C4B -178.41(16) . . . . ? C2B C3B C4B C5B -1.5(3) . . . . ? C3B C4B C5B C6B 1.2(3) . . . . ? C4B C5B C6B C7B -0.2(3) . . . . ? C5B C6B C7B C2B -0.3(3) . . . . ? C5B C6B C7B S1B 174.87(13) . . . . ? C3B C2B C7B C6B -0.1(3) . . . . ? C1B C2B C7B C6B 179.40(15) . . . . ? C3B C2B C7B S1B -176.00(13) . . . . ? C1B C2B C7B S1B 3.49(18) . . . . ? O2B S1B C7B C6B -63.54(18) . . . . ? O1B S1B C7B C6B 69.75(18) . . . . ? N1B S1B C7B C6B -177.66(16) . . . . ? O2B S1B C7B C2B 112.14(13) . . . . ? O1B S1B C7B C2B -114.57(13) . . . . ? N1B S1B C7B C2B -1.98(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2A H2AA O3B 0.878(5) 1.939(6) 2.814(2) 174(2) . N1B H1BA O1A 0.881(5) 1.891(6) 2.7664(19) 173(2) . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.740 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.075