Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Andreas Schmidt' _publ_contact_author_address ; Institute of Organic Chemistry Clausthal University of Technology Leibnizstrasse 6 Clausthal-Zellerfeld D-38678 GERMANY ; _publ_contact_author_email SCHMIDT@IOC.TU-CLAUSTHAL.DE _publ_requested_coeditor_name ? _publ_contact_letter ; enclosed you will fond the necessary data of our publication in Org. Biomol. Chem. ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Syntheses, pi-stacking interactions, and base-pairings of uracil-pyridinium salts and uracilyl-betaines with nucleobases ; loop_ _publ_author_name _publ_author_address A.Schmidt ; Institut fur Organische Chemie Technische Universitat Clausthal Leibnitzstr. 6 D-38678 Clausthal-Zellerfeld Bundesrepublik Deutschland ; A.Lindner ; Institut fur Organische Chemie Technische Universitat Clausthal Leibnitzstr. 6 D-38678 Clausthal-Zellerfeld Bundesrepublik Deutschland ; M.Nieger ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; M.D.Ruiz-Delgado ; Department of Physikal Chemistry Faculty of Sciences University of Malaga E-29071 Malaga Spain ; F.J.Ramirez ; Department of Physikal Chemistry Faculty of Sciences University of Malaga E-29071 Malaga Spain ; #============================================================================== data_schm30_compound_10 _database_code_depnum_ccdc_archive 'CCDC 605902' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-4-morpholin-4-yl- pyridinium chloride ; _chemical_name_common ; 1-(2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-4-morpholin-4- yl-pyridinium chloride ; _chemical_melting_point ? _chemical_formula_moiety '[C13 H15 N4 O3]+ [Cl]- (H2 O)' _chemical_formula_sum 'C13 H17 Cl N4 O4' _chemical_formula_weight 328.76 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' 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 P21/n _symmetry_Int_Tables_number 14 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 6.9530(1) _cell_length_b 7.9824(2) _cell_length_c 26.3031(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.122(1) _cell_angle_gamma 90.00 _cell_volume 1458.86(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2267 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 40 sec./deg., 1 deg., 2 sets, 214 frames, mos.= 0.456(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7161 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3239 _reflns_number_gt 2805 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.3866P] 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 3239 _refine_ls_number_parameters 211 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Cl1 Cl 0.70196(4) 0.97618(4) 0.290996(11) 0.01746(10) Uani 1 1 d . . . N1 N 0.48028(16) 0.74949(14) 0.11184(4) 0.0180(2) Uani 1 1 d D . . H1 H 0.530(2) 0.7544(18) 0.0832(5) 0.022 Uiso 1 1 d D . . C2 C 0.30007(19) 0.67755(16) 0.11563(5) 0.0192(3) Uani 1 1 d . . . O2 O 0.20982(14) 0.63347(13) 0.07671(4) 0.0290(2) Uani 1 1 d . . . C3 C 0.23629(18) 0.65752(16) 0.16695(5) 0.0180(3) Uani 1 1 d . . . H3 H 0.1176 0.6041 0.1734 0.022 Uiso 1 1 calc R . . C4 C 0.34986(18) 0.71674(14) 0.20506(5) 0.0143(2) Uani 1 1 d . . . N5 N 0.51775(15) 0.79960(13) 0.19821(4) 0.0151(2) Uani 1 1 d D . . H5 H 0.581(2) 0.8469(17) 0.2238(5) 0.018 Uiso 1 1 d D . . C6 C 0.59390(18) 0.81491(15) 0.15094(5) 0.0171(3) Uani 1 1 d . . . O6 O 0.74622(13) 0.88535(12) 0.14401(4) 0.0241(2) Uani 1 1 d . . . N7 N 0.30283(14) 0.69734(12) 0.25733(4) 0.0136(2) Uani 1 1 d . . . C8 C 0.12307(17) 0.73689(15) 0.27284(5) 0.0151(3) Uani 1 1 d . . . H8 H 0.0291 0.7762 0.2486 0.018 Uiso 1 1 calc R . . C9 C 0.07611(18) 0.72127(15) 0.32210(5) 0.0155(3) Uani 1 1 d . . . H9 H -0.0503 0.7492 0.3317 0.019 Uiso 1 1 calc R . . C10 C 0.21277(17) 0.66381(15) 0.35969(5) 0.0145(2) Uani 1 1 d . . . C11 C 0.39516(18) 0.61520(15) 0.34152(5) 0.0157(3) Uani 1 1 d . . . H11 H 0.4892 0.5686 0.3645 0.019 Uiso 1 1 calc R . . C12 C 0.43612(17) 0.63452(15) 0.29194(5) 0.0150(3) Uani 1 1 d . . . H12 H 0.5599 0.6039 0.2809 0.018 Uiso 1 1 calc R . . N13 N 0.17214(15) 0.65581(14) 0.40919(4) 0.0172(2) Uani 1 1 d . . . C14 C -0.02309(18) 0.67580(17) 0.42823(5) 0.0192(3) Uani 1 1 d . . . H14A H -0.0718 0.5659 0.4395 0.023 Uiso 1 1 calc R . . H14B H -0.1107 0.7176 0.4005 0.023 Uiso 1 1 calc R . . C15 C -0.02036(19) 0.79771(17) 0.47220(5) 0.0204(3) Uani 1 1 d . . . H15A H 0.0202 0.9096 0.4604 0.024 Uiso 1 1 calc R . . H15B H -0.1513 0.8079 0.4855 0.024 Uiso 1 1 calc R . . O16 O 0.11031(14) 0.74011(12) 0.51177(3) 0.0229(2) Uani 1 1 d . . . C17 C 0.30149(19) 0.73357(19) 0.49381(5) 0.0248(3) Uani 1 1 d . . . H17A H 0.3913 0.6982 0.5219 0.030 Uiso 1 1 calc R . . H17B H 0.3404 0.8466 0.4826 0.030 Uiso 1 1 calc R . . C18 C 0.3141(2) 0.61096(18) 0.44953(5) 0.0231(3) Uani 1 1 d . . . H18A H 0.4450 0.6142 0.4360 0.028 Uiso 1 1 calc R . . H18B H 0.2893 0.4957 0.4615 0.028 Uiso 1 1 calc R . . O1W O -0.11667(18) 0.42187(16) 0.09020(4) 0.0381(3) Uani 1 1 d D . . H1WA H -0.143(3) 0.440(3) 0.1210(6) 0.057 Uiso 1 1 d D . . H1WB H -0.038(3) 0.495(2) 0.0828(8) 0.057 Uiso 1 1 d 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 Cl1 0.01531(16) 0.02001(16) 0.01703(16) -0.00207(11) 0.00024(11) 0.00020(11) N1 0.0199(6) 0.0239(6) 0.0105(5) -0.0002(4) 0.0043(4) -0.0052(4) C2 0.0211(7) 0.0222(6) 0.0145(6) -0.0009(5) 0.0029(5) -0.0047(5) O2 0.0295(5) 0.0446(6) 0.0128(5) -0.0043(4) 0.0010(4) -0.0155(5) C3 0.0174(6) 0.0229(6) 0.0138(6) -0.0007(5) 0.0028(5) -0.0054(5) C4 0.0156(6) 0.0142(5) 0.0133(6) 0.0010(5) 0.0032(4) 0.0011(5) N5 0.0156(5) 0.0167(5) 0.0129(5) -0.0004(4) 0.0000(4) -0.0033(4) C6 0.0188(6) 0.0166(6) 0.0159(6) 0.0020(5) 0.0029(5) -0.0013(5) O6 0.0210(5) 0.0305(5) 0.0210(5) 0.0028(4) 0.0045(4) -0.0106(4) N7 0.0148(5) 0.0160(5) 0.0103(5) 0.0001(4) 0.0020(4) -0.0006(4) C8 0.0133(6) 0.0155(6) 0.0165(6) -0.0004(5) 0.0002(5) 0.0001(5) C9 0.0137(6) 0.0176(6) 0.0155(6) -0.0012(5) 0.0023(5) 0.0016(5) C10 0.0174(6) 0.0128(5) 0.0133(6) -0.0013(4) 0.0016(5) -0.0002(5) C11 0.0155(6) 0.0176(6) 0.0140(6) 0.0001(5) 0.0003(5) 0.0028(5) C12 0.0132(6) 0.0157(6) 0.0164(6) -0.0013(5) 0.0014(5) 0.0015(5) N13 0.0156(5) 0.0247(6) 0.0114(5) 0.0000(4) 0.0022(4) 0.0044(4) C14 0.0170(6) 0.0270(7) 0.0140(6) -0.0019(5) 0.0048(5) 0.0010(5) C15 0.0222(7) 0.0256(7) 0.0135(6) -0.0005(5) 0.0027(5) 0.0063(5) O16 0.0238(5) 0.0348(5) 0.0103(4) 0.0004(4) 0.0025(4) 0.0055(4) C17 0.0209(7) 0.0396(8) 0.0138(6) -0.0007(6) 0.0004(5) 0.0029(6) C18 0.0223(7) 0.0345(8) 0.0125(6) 0.0027(5) 0.0012(5) 0.0093(6) O1W 0.0409(7) 0.0520(7) 0.0217(6) -0.0059(5) 0.0031(5) -0.0239(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 C6 1.3763(17) . ? N1 C2 1.3852(17) . ? N1 H1 0.842(13) . ? C2 O2 1.2321(16) . ? C2 C3 1.4452(17) . ? C3 C4 1.3390(18) . ? C3 H3 0.9500 . ? C4 N5 1.3594(16) . ? C4 N7 1.4335(15) . ? N5 C6 1.3747(16) . ? N5 H5 0.875(13) . ? C6 O6 1.2187(15) . ? N7 C8 1.3660(15) . ? N7 C12 1.3698(16) . ? C8 C9 1.3535(17) . ? C8 H8 0.9500 . ? C9 C10 1.4217(17) . ? C9 H9 0.9500 . ? C10 N13 1.3439(15) . ? C10 C11 1.4256(17) . ? C11 C12 1.3538(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? N13 C18 1.4664(16) . ? N13 C14 1.4729(16) . ? C14 C15 1.5110(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O16 1.4319(16) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O16 C17 1.4281(16) . ? C17 C18 1.5263(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O1W H1WA 0.849(15) . ? O1W H1WB 0.828(15) . ? 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 C6 N1 C2 126.82(11) . . ? C6 N1 H1 114.0(11) . . ? C2 N1 H1 119.1(11) . . ? O2 C2 N1 119.52(11) . . ? O2 C2 C3 125.45(12) . . ? N1 C2 C3 115.01(11) . . ? C4 C3 C2 117.86(11) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 N5 123.92(11) . . ? C3 C4 N7 122.05(11) . . ? N5 C4 N7 114.03(10) . . ? C4 N5 C6 121.63(11) . . ? C4 N5 H5 121.2(10) . . ? C6 N5 H5 117.2(10) . . ? O6 C6 N5 122.83(12) . . ? O6 C6 N1 122.77(12) . . ? N5 C6 N1 114.35(11) . . ? C8 N7 C12 119.35(10) . . ? C8 N7 C4 120.35(10) . . ? C12 N7 C4 120.28(10) . . ? C9 C8 N7 121.36(12) . . ? C9 C8 H8 119.3 . . ? N7 C8 H8 119.3 . . ? C8 C9 C10 121.11(11) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N13 C10 C9 122.01(11) . . ? N13 C10 C11 122.24(11) . . ? C9 C10 C11 115.75(11) . . ? C12 C11 C10 120.89(12) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 N7 121.36(11) . . ? C11 C12 H12 119.3 . . ? N7 C12 H12 119.3 . . ? C10 N13 C18 123.55(10) . . ? C10 N13 C14 123.62(11) . . ? C18 N13 C14 112.61(10) . . ? N13 C14 C15 110.15(11) . . ? N13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? N13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? O16 C15 C14 109.83(10) . . ? O16 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? O16 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 O16 C15 110.16(10) . . ? O16 C17 C18 110.88(11) . . ? O16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N13 C18 C17 109.85(11) . . ? N13 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? N13 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? H1WA O1W H1WB 106(2) . . ? 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 C6 N1 C2 O2 175.53(12) . . . . ? C6 N1 C2 C3 -5.87(19) . . . . ? O2 C2 C3 C4 -178.17(13) . . . . ? N1 C2 C3 C4 3.32(18) . . . . ? C2 C3 C4 N5 2.43(19) . . . . ? C2 C3 C4 N7 -177.59(11) . . . . ? C3 C4 N5 C6 -6.45(19) . . . . ? N7 C4 N5 C6 173.57(10) . . . . ? C4 N5 C6 O6 -178.34(12) . . . . ? C4 N5 C6 N1 3.95(17) . . . . ? C2 N1 C6 O6 -175.43(13) . . . . ? C2 N1 C6 N5 2.29(18) . . . . ? C3 C4 N7 C8 -48.60(17) . . . . ? N5 C4 N7 C8 131.38(12) . . . . ? C3 C4 N7 C12 129.57(13) . . . . ? N5 C4 N7 C12 -50.45(15) . . . . ? C12 N7 C8 C9 2.53(18) . . . . ? C4 N7 C8 C9 -179.28(11) . . . . ? N7 C8 C9 C10 0.34(18) . . . . ? C8 C9 C10 N13 176.43(12) . . . . ? C8 C9 C10 C11 -3.63(17) . . . . ? N13 C10 C11 C12 -175.81(11) . . . . ? C9 C10 C11 C12 4.26(17) . . . . ? C10 C11 C12 N7 -1.62(18) . . . . ? C8 N7 C12 C11 -1.88(18) . . . . ? C4 N7 C12 C11 179.93(11) . . . . ? C9 C10 N13 C18 -174.61(12) . . . . ? C11 C10 N13 C18 5.45(19) . . . . ? C9 C10 N13 C14 11.24(18) . . . . ? C11 C10 N13 C14 -168.70(11) . . . . ? C10 N13 C14 C15 -131.99(12) . . . . ? C18 N13 C14 C15 53.29(14) . . . . ? N13 C14 C15 O16 -57.66(14) . . . . ? C14 C15 O16 C17 62.47(14) . . . . ? C15 O16 C17 C18 -61.48(14) . . . . ? C10 N13 C18 C17 133.66(12) . . . . ? C14 N13 C18 C17 -51.62(15) . . . . ? O16 C17 C18 N13 55.30(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 H1 O16 0.842(13) 1.980(13) 2.8159(14) 171.9(15) 4_675 N5 H5 Cl1 0.875(13) 2.188(13) 3.0582(11) 172.4(13) . O1W H1WA Cl1 0.849(15) 2.384(15) 3.2314(12) 176(2) 2_545 O1W H1WB O2 0.828(15) 2.059(16) 2.8622(15) 163(2) . C3 H3 Cl1 0.95 2.65 3.5853(13) 169.3 2_545 C9 H9 Cl1 0.95 2.69 3.3793(13) 129.5 1_455 C12 H12 Cl1 0.95 2.76 3.6187(12) 151.5 2_645 C11 H11 O6 0.95 2.37 3.1078(15) 134.5 2_645 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.247 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.046 #============================================================================== data_schmidt4_(ade(H+)2-2Cl-) _database_code_depnum_ccdc_archive 'CCDC 605903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; adeninediium dichloride ; _chemical_name_common 'adeninediium dichloride' _chemical_formula_moiety 'C5 H7 N5 Cl2' _chemical_formula_sum 'C5 H7 N5 Cl2' _chemical_formula_weight 208.06 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 13.4485(12) _cell_length_b 6.4673(6) _cell_length_c 9.3711(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 815.06(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3396 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour coorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.744 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min '0.7551 (theor.)' _exptl_absorpt_correction_T_max '0.8655 (theor.)' _exptl_special_details ; dx = 39.966(4) mm, 2 x 60 sec., 2 deg., 85 frames, mos.= 0.634(4) ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3163 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 28.26 _reflns_number_total 997 _reflns_number_gt 866 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0812P] 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 997 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.43590(3) 0.2500 0.61042(5) 0.02432(18) Uani 1 d S . . Cl2 Cl 0.30140(3) 0.2500 -0.05769(5) 0.01910(17) Uani 1 d S . . N1 N 0.02105(11) 0.2500 0.33199(18) 0.0192(4) Uani 1 d S . . C2 C 0.07406(13) 0.2500 0.2150(2) 0.0186(4) Uani 1 d S . . H2 H 0.0395 0.2500 0.1266 0.022 Uiso 1 calc SR . . N3 N 0.17541(11) 0.2500 0.21090(18) 0.0178(4) Uani 1 d S . . H3 H 0.2044 0.2500 0.1267 0.021 Uiso 1 calc SR . . C4 C 0.23456(13) 0.2500 0.3285(2) 0.0148(4) Uani 1 d S . . N4 N 0.33129(11) 0.2500 0.31534(19) 0.0203(4) Uani 1 d S . . H4A H 0.3585 0.2500 0.2299 0.024 Uiso 1 calc SR . . H4B H 0.3692 0.2500 0.3919 0.024 Uiso 1 calc SR . . C4A C 0.18044(13) 0.2500 0.4562(2) 0.0155(4) Uani 1 d S . . N5 N 0.20743(11) 0.2500 0.59785(17) 0.0155(4) Uani 1 d S . . H5 H 0.2687 0.2500 0.6309 0.019 Uiso 1 calc SR . . C6 C 0.12522(12) 0.2500 0.6759(2) 0.0174(4) Uani 1 d S . . H6 H 0.1232 0.2500 0.7773 0.021 Uiso 1 calc SR . . N7 N 0.04542(11) 0.2500 0.59022(17) 0.0168(4) Uani 1 d S . . H7 H -0.0170 0.2500 0.6182 0.020 Uiso 1 calc SR . . C7A C 0.07803(13) 0.2500 0.45093(19) 0.0141(4) Uani 1 d S . . 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 Cl1 0.0123(3) 0.0438(3) 0.0169(3) 0.000 -0.00099(17) 0.000 Cl2 0.0161(3) 0.0233(3) 0.0179(3) 0.000 0.00208(18) 0.000 N1 0.0107(7) 0.0259(9) 0.0210(9) 0.000 -0.0009(7) 0.000 C2 0.0128(9) 0.0288(10) 0.0142(10) 0.000 -0.0020(7) 0.000 N3 0.0130(8) 0.0267(9) 0.0137(9) 0.000 0.0031(6) 0.000 C4 0.0120(9) 0.0159(9) 0.0166(11) 0.000 -0.0002(7) 0.000 N4 0.0105(8) 0.0354(10) 0.0150(9) 0.000 0.0015(6) 0.000 C4A 0.0113(8) 0.0159(9) 0.0195(11) 0.000 0.0006(7) 0.000 N5 0.0092(8) 0.0235(8) 0.0139(9) 0.000 -0.0015(6) 0.000 C6 0.0128(9) 0.0210(10) 0.0183(10) 0.000 0.0017(8) 0.000 N7 0.0092(7) 0.0228(8) 0.0183(9) 0.000 0.0025(6) 0.000 C7A 0.0115(9) 0.0157(9) 0.0153(11) 0.000 0.0011(7) 0.000 _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 C2 1.308(2) . ? N1 C7A 1.353(2) . ? C2 N3 1.364(2) . ? C2 H2 0.9500 . ? N3 C4 1.359(2) . ? N3 H3 0.8800 . ? C4 N4 1.307(2) . ? C4 C4A 1.401(3) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C4A N5 1.376(3) . ? C4A C7A 1.378(2) . ? N5 C6 1.326(2) . ? N5 H5 0.8800 . ? C6 N7 1.340(2) . ? C6 H6 0.9500 . ? N7 C7A 1.377(2) . ? N7 H7 0.8800 . ? 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 C2 N1 C7A 112.45(16) . . ? N1 C2 N3 124.67(19) . . ? N1 C2 H2 117.7 . . ? N3 C2 H2 117.7 . . ? C4 N3 C2 124.20(17) . . ? C4 N3 H3 117.9 . . ? C2 N3 H3 117.9 . . ? N4 C4 N3 120.41(18) . . ? N4 C4 C4A 126.73(18) . . ? N3 C4 C4A 112.86(16) . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N5 C4A C7A 107.35(16) . . ? N5 C4A C4 133.40(17) . . ? C7A C4A C4 119.26(17) . . ? C6 N5 C4A 108.20(16) . . ? C6 N5 H5 125.9 . . ? C4A N5 H5 125.9 . . ? N5 C6 N7 109.69(18) . . ? N5 C6 H6 125.2 . . ? N7 C6 H6 125.2 . . ? C6 N7 C7A 108.24(15) . . ? C6 N7 H7 125.9 . . ? C7A N7 H7 125.9 . . ? N1 C7A N7 126.92(16) . . ? N1 C7A C4A 126.56(17) . . ? N7 C7A C4A 106.52(16) . . ? 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 C7A N1 C2 N3 0.0 . . . . ? N1 C2 N3 C4 0.0 . . . . ? C2 N3 C4 N4 180.0 . . . . ? C2 N3 C4 C4A 0.0 . . . . ? N4 C4 C4A N5 0.0 . . . . ? N3 C4 C4A N5 180.0 . . . . ? N4 C4 C4A C7A 180.0 . . . . ? N3 C4 C4A C7A 0.0 . . . . ? C7A C4A N5 C6 0.0 . . . . ? C4 C4A N5 C6 180.0 . . . . ? C4A N5 C6 N7 0.0 . . . . ? N5 C6 N7 C7A 0.0 . . . . ? C2 N1 C7A N7 180.0 . . . . ? C2 N1 C7A C4A 0.0 . . . . ? C6 N7 C7A N1 180.0 . . . . ? C6 N7 C7A C4A 0.0 . . . . ? N5 C4A C7A N1 180.0 . . . . ? C4 C4A C7A N1 0.0 . . . . ? N5 C4A C7A N7 0.0 . . . . ? C4 C4A C7A N7 180.0 . . . . ? 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 N3 H3 Cl2 0.88 2.17 3.0342(17) 169.2 . N4 H4A Cl2 0.88 2.80 3.5187(18) 139.5 . N4 H4B Cl1 0.88 2.24 3.1025(17) 168.2 . N5 H5 Cl1 0.88 2.26 3.0748(15) 154.5 . N4 H4A N1 0.88 2.26 2.901(2) 129.5 6_656 N5 H5 Cl2 0.88 2.95 3.4665(17) 119.2 1_556 N7 H7 Cl2 0.88 2.51 3.2959(16) 149.6 6_556 N7 H7 Cl1 0.88 2.62 3.1685(17) 121.3 6_557 _diffrn_measured_fraction_theta_max 0.839 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.839 _refine_diff_density_max 0.311 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.055 #============================================================================== #_eof # End of Crystallographic Information File