# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text #TrackingRef '- cif.txt' _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Qiaolin Wu' _publ_contact_author_address ; ' School of Chemistry Jili University Changchun, 130023 P.R. China.' ; _publ_contact_author_email wuql@jlu.edu.cn _publ_contact_author_phone (+86)-431-5168376 _publ_contact_author_fax (+86)-431-5193421 loop_ _publ_author_name _publ_author_address 'Qing Su' ; School of Chemistry Jilin University Changchun, Jilin. 130012 P.R.China ; 'Mina He' ; School of Chemistry Jilin University Changchun, Jilin. 130012 P.R.China ; 'Qiaolin Wu' ; School of Chemistry Jilin University Changchun, Jilin. 130012 P.R.China ; 'Wei Gao' ; School of Chemistry Jilin University Changchun, Jilin. 130012 P.R.China ; 'Hai Xu' ; School of Chemistry Jilin University Changchun, Jilin. 130012 P.R.China ; 'Ling Ye' ; School of Chemistry Jilin University Changchun,Jilin. 130012 P.R.China ; 'Ying Mu' ; School of Chemistry Jilin University Changchun,Jilin. 130012 P.R.China ; data_1 #TrackingRef '- cif.txt' _database_code_depnum_ccdc_archive 'CCDC 866261' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 Cl N2' _chemical_formula_sum 'C11 H13 Cl N2' _chemical_formula_weight 208.68 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0715(14) _cell_length_b 9.0663(18) _cell_length_c 17.098(3) _cell_angle_alpha 92.53(3) _cell_angle_beta 101.12(3) _cell_angle_gamma 102.62(3) _cell_volume 1045.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8215 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9413 _exptl_absorpt_correction_T_max 0.9482 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10332 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4741 _reflns_number_gt 3574 _reflns_threshold_expression >2sigma(I) _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL-XP _computing_publication_material 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^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4741 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 Cl1 Cl 0.36436(10) 0.13095(6) 0.14267(3) 0.05279(19) Uani 1 1 d . . . Cl2 Cl 0.63166(9) 0.62955(6) 0.34897(3) 0.05320(18) Uani 1 1 d . . . N1 N 0.2615(2) 0.30307(16) 0.99401(8) 0.0312(3) Uani 1 1 d . . . N2 N 0.3773(3) 0.7401(2) 1.18057(11) 0.0519(5) Uani 1 1 d . . . N3 N 0.7412(2) -0.03867(19) 0.43274(9) 0.0369(3) Uani 1 1 d . . . N4 N 0.6914(3) -0.2683(2) 0.67870(12) 0.0552(5) Uani 1 1 d . . . C1 C 0.2081(3) 0.2322(2) 0.92039(10) 0.0338(4) Uani 1 1 d . . . C2 C 0.1564(3) 0.3134(2) 0.85593(10) 0.0374(4) Uani 1 1 d . . . H2 H 0.1214 0.2647 0.8045 0.045 Uiso 1 1 calc R . . C3 C 0.1556(3) 0.4648(2) 0.86661(10) 0.0351(4) Uani 1 1 d . . . C4 C 0.2084(2) 0.53745(19) 0.94505(10) 0.0314(4) Uani 1 1 d . . . C5 C 0.2644(2) 0.45325(18) 1.01014(10) 0.0290(3) Uani 1 1 d . . . C6 C 0.2086(3) 0.6911(2) 0.96409(11) 0.0396(4) Uani 1 1 d . . . H6 H 0.1713 0.7499 0.9232 0.048 Uiso 1 1 calc R . . C7 C 0.2621(3) 0.7539(2) 1.04069(12) 0.0412(4) Uani 1 1 d . . . H7 H 0.2595 0.8548 1.0514 0.049 Uiso 1 1 calc R . . C8 C 0.3223(3) 0.6692(2) 1.10529(11) 0.0364(4) Uani 1 1 d . . . C9 C 0.3226(3) 0.5184(2) 1.08939(10) 0.0334(4) Uani 1 1 d . . . H9 H 0.3610 0.4610 1.1308 0.040 Uiso 1 1 calc R . . C10 C 0.2049(4) 0.0671(2) 0.91206(12) 0.0468(5) Uani 1 1 d . . . H10A H 0.2828 0.0409 0.9596 0.070 Uiso 1 1 calc R . . H10B H 0.2590 0.0452 0.8667 0.070 Uiso 1 1 calc R . . H10C H 0.0709 0.0090 0.9046 0.070 Uiso 1 1 calc R . . C11 C 0.1004(4) 0.5492(3) 0.79546(11) 0.0538(6) Uani 1 1 d . . . H11A H 0.1020 0.4906 0.7475 0.081 Uiso 1 1 calc R . . H11B H 0.1939 0.6451 0.8001 0.081 Uiso 1 1 calc R . . H11C H -0.0299 0.5659 0.7932 0.081 Uiso 1 1 calc R . . C12 C 0.7620(3) 0.0805(2) 0.38926(11) 0.0388(4) Uani 1 1 d . . . C13 C 0.7869(3) 0.2248(2) 0.42627(12) 0.0416(4) Uani 1 1 d . . . H13 H 0.8002 0.3078 0.3960 0.050 Uiso 1 1 calc R . . C14 C 0.7925(3) 0.2473(2) 0.50670(12) 0.0394(4) Uani 1 1 d . . . C15 C 0.7773(2) 0.1200(2) 0.55264(11) 0.0350(4) Uani 1 1 d . . . C16 C 0.7461(2) -0.0269(2) 0.51349(10) 0.0338(4) Uani 1 1 d . . . C17 C 0.7865(3) 0.1291(2) 0.63655(12) 0.0418(4) Uani 1 1 d . . . H17 H 0.8100 0.2235 0.6649 0.050 Uiso 1 1 calc R . . C18 C 0.7615(3) 0.0020(2) 0.67567(11) 0.0419(4) Uani 1 1 d . . . H18 H 0.7711 0.0115 0.7308 0.050 Uiso 1 1 calc R . . C19 C 0.7208(3) -0.1454(2) 0.63533(11) 0.0393(4) Uani 1 1 d . . . C20 C 0.7174(3) -0.1580(2) 0.55398(11) 0.0388(4) Uani 1 1 d . . . H20 H 0.6962 -0.2530 0.5265 0.047 Uiso 1 1 calc R . . C21 C 0.7523(3) 0.0512(3) 0.30195(12) 0.0491(5) Uani 1 1 d . . . H21A H 0.7485 -0.0539 0.2897 0.074 Uiso 1 1 calc R . . H21B H 0.8670 0.1132 0.2878 0.074 Uiso 1 1 calc R . . H21C H 0.6350 0.0754 0.2722 0.074 Uiso 1 1 calc R . . C22 C 0.8095(4) 0.4030(2) 0.54568(15) 0.0559(6) Uani 1 1 d . . . H22A H 0.8066 0.4739 0.5057 0.084 Uiso 1 1 calc R . . H22B H 0.9320 0.4332 0.5843 0.084 Uiso 1 1 calc R . . H22C H 0.7007 0.4011 0.5719 0.084 Uiso 1 1 calc R . . H100 H 0.292(4) 0.253(3) 1.0417(14) 0.054(6) Uiso 1 1 d . . . H101 H 0.430(3) 0.694(3) 1.2223(14) 0.046(6) Uiso 1 1 d . . . H102 H 0.382(4) 0.831(3) 1.1816(16) 0.067(8) Uiso 1 1 d . . . H103 H 0.713(4) -0.131(3) 0.4068(14) 0.057(7) Uiso 1 1 d . . . H104 H 0.671(4) -0.252(3) 0.7328(16) 0.059(7) Uiso 1 1 d . . . H105 H 0.627(4) -0.360(3) 0.6550(15) 0.061(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0885(4) 0.0367(3) 0.0310(2) 0.00649(19) 0.0050(2) 0.0158(3) Cl2 0.0722(4) 0.0415(3) 0.0443(3) -0.0029(2) 0.0118(3) 0.0114(2) N1 0.0398(8) 0.0264(7) 0.0291(7) 0.0044(6) 0.0070(6) 0.0110(6) N2 0.0688(13) 0.0435(11) 0.0395(9) -0.0116(8) 0.0021(9) 0.0158(10) N3 0.0359(8) 0.0359(8) 0.0351(8) -0.0048(6) 0.0025(6) 0.0065(6) N4 0.0792(14) 0.0398(10) 0.0451(10) 0.0065(8) 0.0103(10) 0.0124(10) C1 0.0397(9) 0.0276(8) 0.0345(8) 0.0003(7) 0.0089(7) 0.0082(7) C2 0.0466(10) 0.0364(9) 0.0282(8) -0.0010(7) 0.0047(8) 0.0112(8) C3 0.0395(9) 0.0352(9) 0.0307(8) 0.0058(7) 0.0055(7) 0.0101(7) C4 0.0344(9) 0.0275(8) 0.0330(8) 0.0043(7) 0.0067(7) 0.0086(7) C5 0.0307(8) 0.0253(8) 0.0313(8) 0.0021(6) 0.0066(7) 0.0071(6) C6 0.0506(11) 0.0279(9) 0.0412(10) 0.0068(7) 0.0060(9) 0.0131(8) C7 0.0511(11) 0.0260(9) 0.0463(10) -0.0006(8) 0.0084(9) 0.0107(8) C8 0.0367(9) 0.0347(9) 0.0360(9) -0.0052(7) 0.0064(7) 0.0068(7) C9 0.0384(9) 0.0319(9) 0.0301(8) 0.0023(7) 0.0060(7) 0.0094(7) C10 0.0691(14) 0.0285(9) 0.0436(11) -0.0010(8) 0.0098(10) 0.0155(9) C11 0.0801(16) 0.0505(13) 0.0328(9) 0.0101(9) 0.0049(10) 0.0240(12) C12 0.0296(9) 0.0451(11) 0.0384(9) 0.0019(8) 0.0024(7) 0.0062(8) C13 0.0381(10) 0.0405(10) 0.0450(10) 0.0073(8) 0.0094(8) 0.0053(8) C14 0.0337(9) 0.0345(10) 0.0490(11) -0.0003(8) 0.0104(8) 0.0052(7) C15 0.0291(8) 0.0350(9) 0.0385(9) -0.0022(7) 0.0052(7) 0.0048(7) C16 0.0282(8) 0.0364(9) 0.0350(9) -0.0012(7) 0.0030(7) 0.0075(7) C17 0.0446(11) 0.0362(10) 0.0421(10) -0.0051(8) 0.0095(8) 0.0056(8) C18 0.0447(10) 0.0454(11) 0.0337(9) -0.0012(8) 0.0073(8) 0.0079(8) C19 0.0368(9) 0.0389(10) 0.0411(10) 0.0030(8) 0.0033(8) 0.0106(8) C20 0.0402(10) 0.0340(9) 0.0411(10) -0.0020(8) 0.0039(8) 0.0110(8) C21 0.0511(12) 0.0551(13) 0.0393(10) 0.0054(9) 0.0069(9) 0.0104(10) C22 0.0723(15) 0.0364(11) 0.0616(14) -0.0001(10) 0.0265(12) 0.0078(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.334(2) . ? N1 C5 1.372(2) . ? N1 H100 0.96(2) . ? N2 C8 1.358(2) . ? N2 H101 0.90(3) . ? N2 H102 0.81(3) . ? N3 C12 1.336(3) . ? N3 C16 1.373(2) . ? N3 H103 0.89(3) . ? N4 C19 1.365(3) . ? N4 H104 0.97(2) . ? N4 H105 0.90(3) . ? C1 C2 1.387(3) . ? C1 C10 1.492(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.412(2) . ? C3 C11 1.499(3) . ? C4 C6 1.416(2) . ? C4 C5 1.420(2) . ? C5 C9 1.401(2) . ? C6 C7 1.353(3) . ? C6 H6 0.9300 . ? C7 C8 1.424(3) . ? C7 H7 0.9300 . ? C8 C9 1.383(2) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.388(3) . ? C12 C21 1.491(3) . ? C13 C14 1.373(3) . ? C13 H13 0.9300 . ? C14 C15 1.420(3) . ? C14 C22 1.504(3) . ? C15 C16 1.417(2) . ? C15 C17 1.421(3) . ? C16 C20 1.398(3) . ? C17 C18 1.353(3) . ? C17 H17 0.9300 . ? C18 C19 1.421(3) . ? C18 H18 0.9300 . ? C19 C20 1.386(3) . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 123.35(15) . . ? C1 N1 H100 124.0(14) . . ? C5 N1 H100 112.5(14) . . ? C8 N2 H101 121.5(15) . . ? C8 N2 H102 113(2) . . ? H101 N2 H102 124(3) . . ? C12 N3 C16 123.58(17) . . ? C12 N3 H103 117.6(15) . . ? C16 N3 H103 118.6(15) . . ? C19 N4 H104 118.0(15) . . ? C19 N4 H105 121.1(16) . . ? H104 N4 H105 113(2) . . ? N1 C1 C2 119.18(16) . . ? N1 C1 C10 117.54(16) . . ? C2 C1 C10 123.28(16) . . ? C3 C2 C1 121.34(16) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 118.82(16) . . ? C2 C3 C11 119.85(17) . . ? C4 C3 C11 121.33(17) . . ? C3 C4 C6 124.26(16) . . ? C3 C4 C5 119.04(16) . . ? C6 C4 C5 116.70(16) . . ? N1 C5 C9 119.47(15) . . ? N1 C5 C4 118.24(15) . . ? C9 C5 C4 122.29(16) . . ? C7 C6 C4 121.17(17) . . ? C7 C6 H6 119.4 . . ? C4 C6 H6 119.4 . . ? C6 C7 C8 121.61(17) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? N2 C8 C9 122.40(19) . . ? N2 C8 C7 118.52(19) . . ? C9 C8 C7 119.08(16) . . ? C8 C9 C5 119.12(16) . . ? C8 C9 H9 120.4 . . ? C5 C9 H9 120.4 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 119.23(17) . . ? N3 C12 C21 117.92(18) . . ? C13 C12 C21 122.83(18) . . ? C14 C13 C12 121.21(18) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 118.86(17) . . ? C13 C14 C22 120.96(18) . . ? C15 C14 C22 120.16(17) . . ? C16 C15 C14 119.13(17) . . ? C16 C15 C17 116.71(17) . . ? C14 C15 C17 124.14(17) . . ? N3 C16 C20 119.83(17) . . ? N3 C16 C15 117.90(17) . . ? C20 C16 C15 122.26(16) . . ? C18 C17 C15 120.77(18) . . ? C18 C17 H17 119.6 . . ? C15 C17 H17 119.6 . . ? C17 C18 C19 122.16(17) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? N4 C19 C20 122.89(19) . . ? N4 C19 C18 118.62(18) . . ? C20 C19 C18 118.47(18) . . ? C19 C20 C16 119.52(18) . . ? C19 C20 H20 120.2 . . ? C16 C20 H20 120.2 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 H22A 109.5 . . ? C14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 C7 H7 Cl1 0.93 2.77 3.627(2) 154.4 1_566 C18 H18 Cl1 0.93 2.79 3.581(2) 143.7 2_656 C21 H21C Cl1 0.96 2.78 3.691(3) 159.7 . C22 H22C Cl2 0.96 2.90 3.857(2) 175.6 2_666 C10 H10C Cl1 0.96 3.00 3.943(3) 168.9 2_556 N1 H100 Cl1 0.96(2) 2.13(3) 3.0916(17) 176(2) 1_556 N2 H101 Cl2 0.90(3) 2.52(3) 3.402(3) 166(2) 1_556 N2 H102 Cl1 0.81(3) 2.85(3) 3.648(2) 166(3) 1_566 N3 H103 Cl2 0.89(3) 2.25(3) 3.142(2) 176(2) 1_545 N4 H104 Cl1 0.97(2) 2.43(3) 3.373(2) 162(2) 2_656 N4 H105 Cl2 0.90(3) 2.70(3) 3.514(2) 151.5(19) 2_656 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.380 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.090 #====END data_2 #TrackingRef '- cif.txt' _database_code_depnum_ccdc_archive 'CCDC 294744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 Cl N2 O S' _chemical_formula_weight 286.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9883(14) _cell_length_b 17.034(3) _cell_length_c 12.698(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.88(3) _cell_angle_gamma 90.00 _cell_volume 1489.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9834 _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8346 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3411 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3411 _reflns_number_gt 2156 _reflns_threshold_expression >2sigma(I) _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL-XP _computing_publication_material 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^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3411 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 Cl1 Cl 0.19540(15) 0.21216(4) 0.16994(6) 0.0986(3) Uani 1 1 d . . . S1 S 0.26131(11) 0.07626(4) 0.51350(5) 0.0696(2) Uani 1 1 d . . . O1 O 0.2021(4) 0.01370(13) 0.4345(2) 0.1191(9) Uani 1 1 d . . . N1 N 0.2764(2) 0.58673(10) 0.50370(14) 0.0465(4) Uani 1 1 d . . . N2 N 0.2421(4) 0.39993(14) 0.22008(17) 0.0687(6) Uani 1 1 d . . . C1 C 0.2605(2) 0.51054(11) 0.46731(15) 0.0415(4) Uani 1 1 d . . . C2 C 0.2412(3) 0.45021(11) 0.54158(15) 0.0450(4) Uani 1 1 d . . . C3 C 0.2394(3) 0.47039(14) 0.64935(16) 0.0547(5) Uani 1 1 d . . . C4 C 0.2550(3) 0.54869(15) 0.67783(18) 0.0588(6) Uani 1 1 d . . . C5 C 0.2740(3) 0.60672(12) 0.60511(17) 0.0516(5) Uani 1 1 d . . . C6 C 0.2630(3) 0.49492(11) 0.36009(15) 0.0461(4) Uani 1 1 d . . . C7 C 0.2428(3) 0.41811(11) 0.32249(16) 0.0483(5) Uani 1 1 d . . . C8 C 0.2247(3) 0.35685(12) 0.39714(18) 0.0519(5) Uani 1 1 d . . . C9 C 0.2242(3) 0.37233(12) 0.50145(17) 0.0516(5) Uani 1 1 d . . . C10 C 0.2205(6) 0.4082(2) 0.7300(2) 0.0795(8) Uani 1 1 d . . . C11 C 0.2908(5) 0.69178(16) 0.6335(3) 0.0689(7) Uani 1 1 d . . . C12 C 0.0662(5) 0.14391(18) 0.4986(3) 0.1041(10) Uani 1 1 d . . . H12A H 0.0436 0.1641 0.4270 0.156 Uiso 1 1 calc R . . H12B H 0.0979 0.1864 0.5483 0.156 Uiso 1 1 calc R . . H12C H -0.0488 0.1179 0.5126 0.156 Uiso 1 1 calc R . . C13 C 0.4315(4) 0.13605(18) 0.4625(2) 0.0809(7) Uani 1 1 d . . . H13A H 0.5481 0.1066 0.4610 0.121 Uiso 1 1 calc R . . H13B H 0.4611 0.1812 0.5075 0.121 Uiso 1 1 calc R . . H13C H 0.3774 0.1527 0.3914 0.121 Uiso 1 1 calc R . . H1 H 0.285(4) 0.6241(18) 0.453(2) 0.083(8) Uiso 1 1 d . . . H2A H 0.266(4) 0.4371(19) 0.172(2) 0.091(9) Uiso 1 1 d . . . H2B H 0.231(3) 0.3573(17) 0.2034(19) 0.060(7) Uiso 1 1 d . . . H4 H 0.257(4) 0.5621(18) 0.751(2) 0.081(8) Uiso 1 1 d . . . H6 H 0.280(3) 0.5353(13) 0.3152(16) 0.044(5) Uiso 1 1 d . . . H8 H 0.216(3) 0.3055(14) 0.3733(17) 0.056(6) Uiso 1 1 d . . . H9 H 0.216(3) 0.3308(13) 0.5469(16) 0.047(5) Uiso 1 1 d . . . H10A H 0.229(5) 0.433(2) 0.789(3) 0.103(12) Uiso 1 1 d . . . H10B H 0.103(4) 0.3775(18) 0.712(2) 0.094(10) Uiso 1 1 d . . . H10C H 0.329(4) 0.3712(17) 0.7309(19) 0.074(8) Uiso 1 1 d . . . H11A H 0.277(5) 0.723(2) 0.571(3) 0.114(12) Uiso 1 1 d . . . H11B H 0.190(4) 0.7069(16) 0.676(2) 0.085(9) Uiso 1 1 d . . . H11C H 0.407(4) 0.7038(17) 0.678(2) 0.088(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1748(8) 0.0450(3) 0.0672(4) -0.0138(3) -0.0040(4) 0.0045(4) S1 0.1038(5) 0.0508(3) 0.0581(4) 0.0069(3) 0.0251(3) 0.0026(3) O1 0.180(2) 0.0637(12) 0.1322(19) -0.0400(12) 0.0801(17) -0.0307(14) N1 0.0475(9) 0.0401(9) 0.0509(10) -0.0002(7) 0.0061(7) 0.0005(7) N2 0.1104(17) 0.0439(11) 0.0499(11) -0.0045(9) 0.0086(11) -0.0069(11) C1 0.0369(9) 0.0368(9) 0.0504(10) 0.0027(8) 0.0065(7) 0.0012(7) C2 0.0423(10) 0.0447(10) 0.0489(10) 0.0049(8) 0.0102(8) -0.0012(8) C3 0.0520(12) 0.0623(13) 0.0515(12) 0.0056(10) 0.0140(9) -0.0023(10) C4 0.0608(13) 0.0685(14) 0.0495(12) -0.0071(10) 0.0165(10) -0.0014(11) C5 0.0456(11) 0.0507(11) 0.0587(12) -0.0080(10) 0.0097(9) 0.0020(9) C6 0.0533(11) 0.0364(9) 0.0473(11) 0.0067(8) 0.0049(8) -0.0011(8) C7 0.0524(11) 0.0419(10) 0.0483(11) 0.0009(8) 0.0018(8) -0.0008(8) C8 0.0559(12) 0.0351(10) 0.0634(13) 0.0016(9) 0.0068(9) -0.0031(8) C9 0.0584(12) 0.0416(10) 0.0556(12) 0.0110(9) 0.0120(9) -0.0025(9) C10 0.109(3) 0.079(2) 0.0561(16) 0.0110(14) 0.0292(16) -0.0100(18) C11 0.0761(18) 0.0549(14) 0.0755(18) -0.0175(13) 0.0128(15) -0.0007(12) C12 0.100(2) 0.0588(16) 0.161(3) -0.0063(18) 0.042(2) -0.0007(16) C13 0.0836(18) 0.0804(18) 0.0794(17) 0.0105(15) 0.0162(14) -0.0052(15) _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 1.474(2) . ? S1 C13 1.770(3) . ? S1 C12 1.771(3) . ? N1 C5 1.335(3) . ? N1 C1 1.376(2) . ? N1 H1 0.91(3) . ? N2 C7 1.336(3) . ? N2 H2A 0.91(3) . ? N2 H2B 0.76(3) . ? C1 C6 1.390(3) . ? C1 C2 1.417(3) . ? C2 C3 1.413(3) . ? C2 C9 1.419(3) . ? C3 C4 1.381(3) . ? C3 C10 1.495(3) . ? C4 C5 1.375(3) . ? C4 H4 0.95(3) . ? C5 C11 1.493(3) . ? C6 C7 1.392(3) . ? C6 H6 0.91(2) . ? C7 C8 1.430(3) . ? C8 C9 1.351(3) . ? C8 H8 0.92(2) . ? C9 H9 0.92(2) . ? C10 H10A 0.85(3) . ? C10 H10B 0.97(3) . ? C10 H10C 0.98(3) . ? C11 H11A 0.95(4) . ? C11 H11B 1.00(3) . ? C11 H11C 0.92(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C13 107.16(13) . . ? O1 S1 C12 106.06(17) . . ? C13 S1 C12 98.04(15) . . ? C5 N1 C1 123.44(18) . . ? C5 N1 H1 120.9(18) . . ? C1 N1 H1 115.6(18) . . ? C7 N2 H2A 121.1(19) . . ? C7 N2 H2B 118.5(19) . . ? H2A N2 H2B 120(3) . . ? N1 C1 C6 119.72(17) . . ? N1 C1 C2 118.17(18) . . ? C6 C1 C2 122.11(18) . . ? C3 C2 C1 119.07(19) . . ? C3 C2 C9 124.14(18) . . ? C1 C2 C9 116.79(18) . . ? C4 C3 C2 118.4(2) . . ? C4 C3 C10 121.2(2) . . ? C2 C3 C10 120.5(2) . . ? C5 C4 C3 122.1(2) . . ? C5 C4 H4 119.6(19) . . ? C3 C4 H4 118.3(18) . . ? N1 C5 C4 118.9(2) . . ? N1 C5 C11 117.8(2) . . ? C4 C5 C11 123.3(2) . . ? C1 C6 C7 119.89(18) . . ? C1 C6 H6 119.4(13) . . ? C7 C6 H6 120.7(13) . . ? N2 C7 C6 122.35(19) . . ? N2 C7 C8 119.36(19) . . ? C6 C7 C8 118.29(19) . . ? C9 C8 C7 121.53(19) . . ? C9 C8 H8 119.6(14) . . ? C7 C8 H8 118.8(14) . . ? C8 C9 C2 121.36(18) . . ? C8 C9 H9 118.4(13) . . ? C2 C9 H9 120.2(13) . . ? C3 C10 H10A 104(2) . . ? C3 C10 H10B 113.1(17) . . ? H10A C10 H10B 114(3) . . ? C3 C10 H10C 107.7(15) . . ? H10A C10 H10C 112(3) . . ? H10B C10 H10C 106(2) . . ? C5 C11 H11A 111(2) . . ? C5 C11 H11B 110.4(16) . . ? H11A C11 H11B 109(3) . . ? C5 C11 H11C 112.7(18) . . ? H11A C11 H11C 110(3) . . ? H11B C11 H11C 104(2) . . ? S1 C12 H12A 109.5 . . ? S1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 C8 H8 Cl1 0.92(2) 3.01(2) 3.773(2) 140.4(17) . C12 H12C O1 0.96 2.62 3.463(4) 146.5 3_556 C13 H13A O1 0.96 2.87 3.692(4) 144.6 3_656 N2 H2B Cl1 0.76(3) 2.51(3) 3.267(3) 174(2) . N2 H2A O1 0.91(3) 1.92(3) 2.832(3) 176(3) 2 N1 H1 Cl1 0.91(3) 2.19(3) 3.1007(19) 179(3) 2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.338 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.068 #====END data_3 #TrackingRef '- cif.txt' _database_code_depnum_ccdc_archive 'CCDC 866262' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 N2 O2' _chemical_formula_sum 'C13 H16 N2 O2' _chemical_formula_weight 232.28 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 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 17.755(4) _cell_length_b 7.4749(15) _cell_length_c 18.786(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2493.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13651 _cell_measurement_theta_min 6.30 _cell_measurement_theta_max 54.91 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9809 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21852 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2840 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL-XP _computing_publication_material 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^)+(0.0789P)^2^+0.0662P] 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 2840 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 1.09218(8) 0.2144(2) 0.28579(7) 0.0683(4) Uani 1 1 d . . . O2 O 1.04769(7) 0.03352(19) 0.36866(7) 0.0615(4) Uani 1 1 d . . . N1 N 0.18620(9) 0.03344(18) 0.41464(7) 0.0421(4) Uani 1 1 d . . . N2 N 0.07506(11) 0.2407(2) 0.63169(10) 0.0583(5) Uani 1 1 d . . . C1 C 0.24551(11) -0.0080(2) 0.37383(9) 0.0473(5) Uani 1 1 d . . . C2 C 0.31792(11) 0.0183(2) 0.39986(11) 0.0539(5) Uani 1 1 d . . . H2 H 0.3589 -0.0130 0.3716 0.065 Uiso 1 1 calc R . . C3 C 0.33056(10) 0.0895(2) 0.46634(10) 0.0486(5) Uani 1 1 d . . . C4 C 0.26778(9) 0.1326(2) 0.50911(9) 0.0411(4) Uani 1 1 d . . . C5 C 0.27248(11) 0.2046(2) 0.57845(9) 0.0483(5) Uani 1 1 d . . . H5 H 0.3196 0.2285 0.5978 0.058 Uiso 1 1 calc R . . C6 C 0.20998(11) 0.2398(2) 0.61744(9) 0.0482(5) Uani 1 1 d . . . H6 H 0.2152 0.2895 0.6626 0.058 Uiso 1 1 calc R . . C7 C 0.13691(10) 0.2026(2) 0.59105(9) 0.0433(4) Uani 1 1 d . . . C8 C 0.13011(10) 0.1343(2) 0.52298(9) 0.0414(4) Uani 1 1 d . . . H8 H 0.0826 0.1114 0.5043 0.050 Uiso 1 1 calc R . . C9 C 0.19411(9) 0.0995(2) 0.48211(8) 0.0377(4) Uani 1 1 d . . . C10 C 0.23020(13) -0.0779(3) 0.30089(10) 0.0632(6) Uani 1 1 d . . . H10A H 0.1924 -0.1695 0.3033 0.095 Uiso 1 1 calc R . . H10B H 0.2756 -0.1271 0.2813 0.095 Uiso 1 1 calc R . . H10C H 0.2127 0.0178 0.2711 0.095 Uiso 1 1 calc R . . C11 C 0.40939(11) 0.1223(3) 0.49209(13) 0.0706(6) Uani 1 1 d . . . H11A H 0.4446 0.0855 0.4561 0.106 Uiso 1 1 calc R . . H11B H 0.4181 0.0548 0.5348 0.106 Uiso 1 1 calc R . . H11C H 0.4160 0.2474 0.5018 0.106 Uiso 1 1 calc R . . C12 C 1.03941(11) 0.1422(3) 0.31733(10) 0.0508(5) Uani 1 1 d . . . C13 C 0.95980(14) 0.1833(4) 0.29453(14) 0.0870(8) Uani 1 1 d . . . H13A H 0.9509 0.3096 0.2984 0.130 Uiso 1 1 calc R . . H13B H 0.9251 0.1200 0.3246 0.130 Uiso 1 1 calc R . . H13C H 0.9527 0.1464 0.2460 0.130 Uiso 1 1 calc R . . H1 H 0.1320(14) 0.025(3) 0.3943(12) 0.082(7) Uiso 1 1 d . . . H100 H 0.0851(14) 0.256(3) 0.6768(15) 0.091(8) Uiso 1 1 d . . . H101 H 0.0310(15) 0.181(3) 0.6189(13) 0.086(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0583(9) 0.0936(10) 0.0530(8) 0.0209(7) -0.0028(7) -0.0151(8) O2 0.0542(8) 0.0857(10) 0.0447(8) 0.0167(7) -0.0067(6) -0.0140(7) N1 0.0517(9) 0.0434(8) 0.0313(7) 0.0035(6) -0.0015(6) 0.0025(7) N2 0.0597(12) 0.0783(12) 0.0368(9) -0.0064(8) 0.0064(8) -0.0035(9) C1 0.0627(12) 0.0399(9) 0.0392(10) 0.0064(7) 0.0063(8) 0.0104(9) C2 0.0549(12) 0.0529(11) 0.0541(12) 0.0119(9) 0.0146(9) 0.0149(9) C3 0.0438(10) 0.0477(10) 0.0542(12) 0.0177(9) 0.0008(8) 0.0062(8) C4 0.0395(9) 0.0417(9) 0.0420(10) 0.0115(7) -0.0039(7) -0.0005(7) C5 0.0500(11) 0.0512(10) 0.0438(10) 0.0069(8) -0.0133(8) -0.0085(8) C6 0.0627(12) 0.0483(10) 0.0337(9) -0.0004(7) -0.0066(8) -0.0084(9) C7 0.0516(11) 0.0439(9) 0.0344(9) 0.0048(7) 0.0025(8) -0.0025(8) C8 0.0407(9) 0.0477(9) 0.0359(9) 0.0035(7) -0.0044(7) -0.0021(8) C9 0.0442(9) 0.0370(8) 0.0320(8) 0.0068(7) -0.0031(7) 0.0009(7) C10 0.0910(16) 0.0562(11) 0.0424(11) -0.0019(9) 0.0055(11) 0.0112(11) C11 0.0443(11) 0.0777(15) 0.0899(17) 0.0194(13) -0.0008(11) 0.0051(11) C12 0.0513(11) 0.0649(11) 0.0362(9) -0.0011(9) -0.0007(8) -0.0067(10) C13 0.0604(14) 0.115(2) 0.0858(18) 0.0318(15) -0.0001(13) 0.0087(14) _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 C12 1.233(2) . ? O2 C12 1.269(2) . ? N1 C1 1.339(2) . ? N1 C9 1.367(2) . ? N1 H1 1.04(2) . ? N2 C7 1.368(2) . ? N2 H100 0.87(3) . ? N2 H101 0.93(3) . ? C1 C2 1.390(3) . ? C1 C10 1.491(3) . ? C2 C3 1.376(3) . ? C2 H2 0.9300 . ? C3 C4 1.411(2) . ? C3 C11 1.501(3) . ? C4 C5 1.412(2) . ? C4 C9 1.425(2) . ? C5 C6 1.355(3) . ? C5 H5 0.9300 . ? C6 C7 1.416(3) . ? C6 H6 0.9300 . ? C7 C8 1.382(2) . ? C8 C9 1.396(2) . ? C8 H8 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.509(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C9 122.24(16) . . ? C1 N1 H1 120.3(13) . . ? C9 N1 H1 117.3(13) . . ? C7 N2 H100 114.0(17) . . ? C7 N2 H101 115.4(15) . . ? H100 N2 H101 119(2) . . ? N1 C1 C2 119.56(17) . . ? N1 C1 C10 117.63(18) . . ? C2 C1 C10 122.80(17) . . ? C3 C2 C1 121.68(17) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 118.43(17) . . ? C2 C3 C11 120.51(18) . . ? C4 C3 C11 121.06(18) . . ? C3 C4 C5 124.43(16) . . ? C3 C4 C9 118.88(16) . . ? C5 C4 C9 116.68(16) . . ? C6 C5 C4 121.60(17) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 121.52(16) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? N2 C7 C8 121.56(17) . . ? N2 C7 C6 119.95(17) . . ? C8 C7 C6 118.44(16) . . ? C7 C8 C9 120.44(16) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? N1 C9 C8 119.57(15) . . ? N1 C9 C4 119.15(15) . . ? C8 C9 C4 121.28(16) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 O2 123.85(18) . . ? O1 C12 C13 119.11(18) . . ? O2 C12 C13 117.04(18) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O1 1.04(2) 2.58(2) 3.236(2) 120.7(15) 1_455 N1 H1 O2 1.04(2) 1.57(2) 2.607(2) 173(2) 1_455 N2 H100 O1 0.87(3) 2.06(3) 2.930(2) 172(2) 7_466 N2 H101 O2 0.93(3) 2.14(3) 2.992(2) 152(2) 5_656 C8 H8 O2 0.93 2.69 3.334(2) 127.4 1_455 C10 H10C O1 0.96 2.61 3.295(3) 128.5 1_455 C2 H2 O1 0.93 2.74 3.507(2) 140.4 8_755 C10 H10B O1 0.96 2.63 3.527(3) 155.5 8_755 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.211 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.038 #====END data_4 #TrackingRef '- cif.txt' _database_code_depnum_ccdc_archive 'CCDC 866263' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N2 O2' _chemical_formula_weight 294.34 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)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.339(5) _cell_length_b 7.2309(14) _cell_length_c 18.639(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.50(3) _cell_angle_gamma 90.00 _cell_volume 3030.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15847 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28473 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6913 _reflns_number_gt 3999 _reflns_threshold_expression >2sigma(I) _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-XP _computing_publication_material 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^)+(0.0577P)^2^+0.4654P] 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 SHELXL _refine_ls_extinction_coef 0.0047(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6913 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1150 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.63716(9) -0.1652(2) 0.32840(10) 0.0746(5) Uani 1 1 d . . . O2 O 0.61158(7) 0.0252(2) 0.22792(9) 0.0667(5) Uani 1 1 d . . . O3 O 0.13316(8) 0.6944(2) 0.32468(10) 0.0726(5) Uani 1 1 d . . . O4 O 0.10963(7) 0.4868(2) 0.39520(9) 0.0624(4) Uani 1 1 d . . . N1 N 0.47988(8) 0.3451(2) 0.37094(10) 0.0465(4) Uani 1 1 d . . . N2 N 0.35635(12) 0.2474(4) 0.51480(16) 0.0734(7) Uani 1 1 d . . . N3 N 1.01595(8) 0.6606(2) 0.40323(10) 0.0429(4) Uani 1 1 d . . . N4 N 1.13779(11) 0.7343(3) 0.67178(13) 0.0685(6) Uani 1 1 d . . . C1 C 0.53289(10) 0.3544(3) 0.36488(12) 0.0500(5) Uani 1 1 d . . . C2 C 0.58368(10) 0.3082(3) 0.42848(13) 0.0548(6) Uani 1 1 d . . . H2 H 0.6203 0.3111 0.4236 0.066 Uiso 1 1 calc R . . C3 C 0.58146(10) 0.2583(3) 0.49836(13) 0.0515(6) Uani 1 1 d . . . C4 C 0.52511(10) 0.2482(3) 0.50410(11) 0.0453(5) Uani 1 1 d . . . C5 C 0.47369(9) 0.2933(3) 0.43830(11) 0.0433(5) Uani 1 1 d . . . C6 C 0.41716(10) 0.2910(3) 0.44039(12) 0.0504(5) Uani 1 1 d . . . H6 H 0.3841 0.3194 0.3959 0.060 Uiso 1 1 calc R . . C7 C 0.40988(10) 0.2466(3) 0.50869(13) 0.0525(6) Uani 1 1 d . . . C8 C 0.46120(11) 0.1986(3) 0.57463(13) 0.0564(6) Uani 1 1 d . . . H8 H 0.4569 0.1648 0.6203 0.068 Uiso 1 1 calc R . . C9 C 0.51626(11) 0.2007(3) 0.57274(12) 0.0555(6) Uani 1 1 d . . . H9 H 0.5489 0.1703 0.6173 0.067 Uiso 1 1 calc R . . C10 C 0.53413(11) 0.4203(4) 0.28954(13) 0.0665(7) Uani 1 1 d . . . H10A H 0.4950 0.4599 0.2561 0.100 Uiso 1 1 calc R . . H10B H 0.5468 0.3214 0.2651 0.100 Uiso 1 1 calc R . . H10C H 0.5613 0.5221 0.2989 0.100 Uiso 1 1 calc R . . C11 C 0.63753(11) 0.2200(4) 0.56698(14) 0.0714(7) Uani 1 1 d . . . H11A H 0.6711 0.2354 0.5525 0.107 Uiso 1 1 calc R . . H11B H 0.6368 0.0954 0.5844 0.107 Uiso 1 1 calc R . . H11C H 0.6407 0.3045 0.6081 0.107 Uiso 1 1 calc R . . C12 C 0.96406(9) 0.6663(3) 0.34273(12) 0.0456(5) Uani 1 1 d . . . C13 C 0.91360(10) 0.7254(3) 0.35376(13) 0.0490(5) Uani 1 1 d . . . H13 H 0.8775 0.7310 0.3114 0.059 Uiso 1 1 calc R . . C14 C 0.91570(9) 0.7760(3) 0.42595(12) 0.0453(5) Uani 1 1 d . . . C15 C 0.97095(9) 0.7713(3) 0.48939(11) 0.0405(5) Uani 1 1 d . . . C16 C 1.02210(9) 0.7117(3) 0.47671(11) 0.0394(5) Uani 1 1 d . . . C17 C 1.07770(9) 0.6991(3) 0.53667(12) 0.0457(5) Uani 1 1 d . . . H17 H 1.1103 0.6590 0.5264 0.055 Uiso 1 1 calc R . . C18 C 1.08472(10) 0.7457(3) 0.61128(12) 0.0487(5) Uani 1 1 d . . . C19 C 1.03421(11) 0.8087(3) 0.62487(13) 0.0516(6) Uani 1 1 d . . . H19 H 1.0386 0.8432 0.6748 0.062 Uiso 1 1 calc R . . C20 C 0.97987(10) 0.8195(3) 0.56680(13) 0.0493(5) Uani 1 1 d . . . H20 H 0.9477 0.8595 0.5779 0.059 Uiso 1 1 calc R . . C21 C 0.96322(11) 0.6034(4) 0.26594(12) 0.0604(6) Uani 1 1 d . . . H21A H 1.0018 0.5574 0.2723 0.091 Uiso 1 1 calc R . . H21B H 0.9530 0.7055 0.2303 0.091 Uiso 1 1 calc R . . H21C H 0.9343 0.5069 0.2459 0.091 Uiso 1 1 calc R . . C22 C 0.85990(10) 0.8303(3) 0.43659(15) 0.0615(6) Uani 1 1 d . . . H22A H 0.8271 0.8290 0.3872 0.092 Uiso 1 1 calc R . . H22B H 0.8645 0.9524 0.4583 0.092 Uiso 1 1 calc R . . H22C H 0.8524 0.7444 0.4710 0.092 Uiso 1 1 calc R . . C23 C 0.68629(9) 0.1238(3) 0.34541(11) 0.0438(5) Uani 1 1 d . . . C24 C 0.72603(9) 0.0836(3) 0.42022(12) 0.0531(6) Uani 1 1 d . . . H24 H 0.7276 -0.0356 0.4396 0.064 Uiso 1 1 calc R . . C25 C 0.76319(10) 0.2181(4) 0.46605(13) 0.0622(7) Uani 1 1 d . . . H25 H 0.7901 0.1888 0.5157 0.075 Uiso 1 1 calc R . . C26 C 0.76052(11) 0.3949(4) 0.43848(14) 0.0651(7) Uani 1 1 d . . . H26 H 0.7845 0.4866 0.4701 0.078 Uiso 1 1 calc R . . C27 C 0.72225(11) 0.4373(4) 0.36390(14) 0.0633(6) Uani 1 1 d . . . H27 H 0.7210 0.5568 0.3449 0.076 Uiso 1 1 calc R . . C28 C 0.68584(10) 0.3024(3) 0.31754(13) 0.0547(6) Uani 1 1 d . . . H28 H 0.6606 0.3312 0.2670 0.066 Uiso 1 1 calc R . . C29 C 0.64184(9) -0.0183(3) 0.29760(12) 0.0486(5) Uani 1 1 d . . . C30 C 0.18274(8) 0.4064(3) 0.34668(10) 0.0424(5) Uani 1 1 d . . . C31 C 0.22246(10) 0.4610(4) 0.31330(13) 0.0601(6) Uani 1 1 d . . . H31 H 0.2248 0.5848 0.3012 0.072 Uiso 1 1 calc R . . C32 C 0.25844(11) 0.3322(5) 0.29804(14) 0.0750(8) Uani 1 1 d . . . H32 H 0.2850 0.3699 0.2759 0.090 Uiso 1 1 calc R . . C33 C 0.25539(11) 0.1492(4) 0.31525(14) 0.0730(8) Uani 1 1 d . . . H33 H 0.2789 0.0627 0.3033 0.088 Uiso 1 1 calc R . . C34 C 0.21785(11) 0.0937(4) 0.35000(13) 0.0630(6) Uani 1 1 d . . . H34 H 0.2164 -0.0301 0.3628 0.076 Uiso 1 1 calc R . . C35 C 0.18223(9) 0.2213(3) 0.36604(11) 0.0489(5) Uani 1 1 d . . . H35 H 0.1573 0.1827 0.3904 0.059 Uiso 1 1 calc R . . C36 C 0.13833(9) 0.5422(3) 0.35638(11) 0.0464(5) Uani 1 1 d . . . H100 H 0.4405(12) 0.398(4) 0.3222(15) 0.085(8) Uiso 1 1 d . . . H101 H 1.0503(11) 0.618(3) 0.3968(12) 0.061(7) Uiso 1 1 d . . . H102 H 0.3264(13) 0.275(4) 0.4751(17) 0.078(10) Uiso 1 1 d . . . H103 H 0.3570(12) 0.222(4) 0.5635(16) 0.083(9) Uiso 1 1 d . . . H104 H 1.1685(13) 0.692(4) 0.6629(15) 0.078(9) Uiso 1 1 d . . . H105 H 1.1403(12) 0.744(4) 0.7188(16) 0.077(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0910(14) 0.0613(11) 0.0657(11) -0.0036(9) 0.0236(10) -0.0184(10) O2 0.0584(11) 0.0832(12) 0.0467(9) -0.0073(8) 0.0070(8) -0.0196(9) O3 0.0882(14) 0.0598(11) 0.0716(11) 0.0106(9) 0.0324(10) 0.0142(9) O4 0.0566(10) 0.0726(11) 0.0676(10) 0.0073(9) 0.0343(9) 0.0136(8) N1 0.0442(11) 0.0479(10) 0.0423(10) -0.0010(8) 0.0108(9) 0.0033(8) N2 0.0583(16) 0.1037(19) 0.0588(15) 0.0039(14) 0.0231(13) -0.0110(13) N3 0.0402(10) 0.0458(10) 0.0435(10) 0.0002(8) 0.0169(9) 0.0026(8) N4 0.0575(15) 0.0912(17) 0.0478(13) -0.0129(12) 0.0102(12) -0.0055(12) C1 0.0475(14) 0.0501(13) 0.0507(12) -0.0077(10) 0.0168(11) 0.0035(10) C2 0.0430(13) 0.0601(14) 0.0564(14) -0.0114(11) 0.0136(11) 0.0058(11) C3 0.0455(13) 0.0480(13) 0.0491(12) -0.0105(10) 0.0050(11) 0.0088(10) C4 0.0468(13) 0.0373(11) 0.0423(11) -0.0068(9) 0.0066(10) 0.0048(9) C5 0.0443(13) 0.0371(11) 0.0422(11) -0.0034(9) 0.0096(10) 0.0002(9) C6 0.0423(13) 0.0542(13) 0.0462(12) 0.0017(10) 0.0075(10) -0.0019(10) C7 0.0526(14) 0.0496(13) 0.0528(13) -0.0063(10) 0.0174(12) -0.0080(10) C8 0.0640(16) 0.0555(14) 0.0447(12) -0.0035(10) 0.0153(12) -0.0060(12) C9 0.0593(16) 0.0515(13) 0.0408(12) -0.0023(10) 0.0027(11) 0.0040(11) C10 0.0615(16) 0.0810(18) 0.0594(14) 0.0010(13) 0.0258(13) 0.0079(13) C11 0.0516(16) 0.0857(19) 0.0596(15) -0.0049(13) 0.0022(13) 0.0141(13) C12 0.0444(13) 0.0459(12) 0.0431(11) 0.0059(9) 0.0132(10) 0.0011(9) C13 0.0400(12) 0.0500(13) 0.0517(13) 0.0096(10) 0.0118(10) 0.0042(10) C14 0.0419(13) 0.0391(11) 0.0573(13) 0.0072(10) 0.0215(11) -0.0009(9) C15 0.0427(12) 0.0327(10) 0.0487(12) 0.0028(9) 0.0204(10) -0.0022(8) C16 0.0420(12) 0.0336(10) 0.0435(11) -0.0010(8) 0.0174(10) -0.0033(8) C17 0.0433(13) 0.0450(12) 0.0480(12) -0.0027(10) 0.0166(10) -0.0013(9) C18 0.0489(14) 0.0457(12) 0.0470(12) -0.0028(10) 0.0133(11) -0.0072(10) C19 0.0633(16) 0.0511(13) 0.0456(12) -0.0050(10) 0.0265(12) -0.0089(11) C20 0.0542(14) 0.0442(12) 0.0589(14) -0.0019(10) 0.0322(12) -0.0026(10) C21 0.0561(15) 0.0782(17) 0.0439(12) 0.0036(12) 0.0156(11) 0.0070(13) C22 0.0441(14) 0.0659(15) 0.0793(16) 0.0054(13) 0.0290(13) 0.0011(11) C23 0.0327(11) 0.0596(13) 0.0405(11) -0.0048(10) 0.0157(9) -0.0011(9) C24 0.0404(13) 0.0653(15) 0.0497(12) 0.0055(11) 0.0128(11) 0.0017(11) C25 0.0426(14) 0.0909(19) 0.0444(12) -0.0017(13) 0.0068(11) -0.0103(13) C26 0.0551(16) 0.0761(18) 0.0610(15) -0.0137(13) 0.0186(13) -0.0210(13) C27 0.0615(16) 0.0625(16) 0.0625(15) 0.0008(12) 0.0200(13) -0.0125(13) C28 0.0484(14) 0.0679(15) 0.0465(12) 0.0030(11) 0.0168(11) -0.0034(12) C29 0.0414(13) 0.0618(15) 0.0454(12) -0.0079(11) 0.0198(11) -0.0003(10) C30 0.0321(11) 0.0585(13) 0.0315(10) 0.0005(9) 0.0066(9) -0.0015(9) C31 0.0359(13) 0.0828(17) 0.0573(14) 0.0181(13) 0.0130(11) -0.0012(12) C32 0.0415(14) 0.127(3) 0.0615(16) 0.0269(16) 0.0256(13) 0.0170(15) C33 0.0571(17) 0.107(2) 0.0541(15) 0.0074(15) 0.0205(13) 0.0341(15) C34 0.0640(16) 0.0658(16) 0.0539(14) 0.0034(12) 0.0165(13) 0.0119(13) C35 0.0419(13) 0.0623(14) 0.0417(11) 0.0029(10) 0.0150(10) 0.0006(10) C36 0.0410(12) 0.0559(14) 0.0341(10) -0.0018(10) 0.0053(10) -0.0010(10) _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 C29 1.233(3) . ? O2 C29 1.263(3) . ? O3 C36 1.233(3) . ? O4 C36 1.248(2) . ? N1 C1 1.339(3) . ? N1 C5 1.373(3) . ? N1 H100 1.11(3) . ? N2 C7 1.351(3) . ? N2 H102 0.84(3) . ? N2 H103 0.92(3) . ? N3 C12 1.333(3) . ? N3 C16 1.370(2) . ? N3 H101 0.94(2) . ? N4 C18 1.353(3) . ? N4 H104 0.88(3) . ? N4 H105 0.86(3) . ? C1 C2 1.387(3) . ? C1 C10 1.494(3) . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.418(3) . ? C3 C11 1.496(3) . ? C4 C5 1.415(3) . ? C4 C9 1.419(3) . ? C5 C6 1.391(3) . ? C6 C7 1.388(3) . ? C6 H6 0.9300 . ? C7 C8 1.420(3) . ? C8 C9 1.354(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.388(3) . ? C12 C21 1.494(3) . ? C13 C14 1.376(3) . ? C13 H13 0.9300 . ? C14 C15 1.411(3) . ? C14 C22 1.498(3) . ? C15 C20 1.418(3) . ? C15 C16 1.420(3) . ? C16 C17 1.390(3) . ? C17 C18 1.377(3) . ? C17 H17 0.9300 . ? C18 C19 1.422(3) . ? C19 C20 1.353(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.390(3) . ? C23 C28 1.391(3) . ? C23 C29 1.511(3) . ? C24 C25 1.379(3) . ? C24 H24 0.9300 . ? C25 C26 1.370(4) . ? C25 H25 0.9300 . ? C26 C27 1.379(3) . ? C26 H26 0.9300 . ? C27 C28 1.377(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C30 C35 1.388(3) . ? C30 C31 1.392(3) . ? C30 C36 1.521(3) . ? C31 C32 1.381(4) . ? C31 H31 0.9300 . ? C32 C33 1.371(4) . ? C32 H32 0.9300 . ? C33 C34 1.367(3) . ? C33 H33 0.9300 . ? C34 C35 1.375(3) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 122.52(19) . . ? C1 N1 H100 118.3(13) . . ? C5 N1 H100 118.8(13) . . ? C7 N2 H102 117.7(19) . . ? C7 N2 H103 115.4(18) . . ? H102 N2 H103 127(3) . . ? C12 N3 C16 122.84(18) . . ? C12 N3 H101 120.2(14) . . ? C16 N3 H101 117.0(14) . . ? C18 N4 H104 118.3(18) . . ? C18 N4 H105 121.2(19) . . ? H104 N4 H105 119(3) . . ? N1 C1 C2 119.2(2) . . ? N1 C1 C10 117.5(2) . . ? C2 C1 C10 123.2(2) . . ? C3 C2 C1 121.9(2) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 118.4(2) . . ? C2 C3 C11 120.4(2) . . ? C4 C3 C11 121.2(2) . . ? C5 C4 C3 118.89(19) . . ? C5 C4 C9 116.6(2) . . ? C3 C4 C9 124.5(2) . . ? N1 C5 C6 119.00(19) . . ? N1 C5 C4 119.03(19) . . ? C6 C5 C4 121.95(19) . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N2 C7 C6 122.8(2) . . ? N2 C7 C8 119.0(2) . . ? C6 C7 C8 118.1(2) . . ? C9 C8 C7 121.8(2) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 121.3(2) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 119.33(19) . . ? N3 C12 C21 117.49(19) . . ? C13 C12 C21 123.2(2) . . ? C14 C13 C12 121.5(2) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 118.67(19) . . ? C13 C14 C22 120.2(2) . . ? C15 C14 C22 121.13(19) . . ? C14 C15 C20 124.93(19) . . ? C14 C15 C16 118.87(18) . . ? C20 C15 C16 116.19(19) . . ? N3 C16 C17 119.09(18) . . ? N3 C16 C15 118.75(18) . . ? C17 C16 C15 122.14(18) . . ? C18 C17 C16 120.16(19) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? N4 C18 C17 122.4(2) . . ? N4 C18 C19 119.1(2) . . ? C17 C18 C19 118.5(2) . . ? C20 C19 C18 121.54(19) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C15 121.46(19) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 H22A 109.5 . . ? C14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 118.2(2) . . ? C24 C23 C29 121.0(2) . . ? C28 C23 C29 120.7(2) . . ? C25 C24 C23 120.9(2) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C25 C24 120.0(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.1(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 119.9(2) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 120.8(2) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? O1 C29 O2 124.9(2) . . ? O1 C29 C23 119.0(2) . . ? O2 C29 C23 116.2(2) . . ? C35 C30 C31 117.8(2) . . ? C35 C30 C36 120.93(18) . . ? C31 C30 C36 121.1(2) . . ? C32 C31 C30 120.3(2) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C33 C32 C31 120.5(2) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 120.0(2) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.8(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C30 121.5(2) . . ? C34 C35 H35 119.3 . . ? C30 C35 H35 119.3 . . ? O3 C36 O4 126.0(2) . . ? O3 C36 C30 117.77(19) . . ? O4 C36 C30 116.26(19) . . ? 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 N4 H105 O3 0.86(3) 2.09(3) 2.940(3) 169(3) 4_676 N3 H101 O4 0.94(2) 1.74(2) 2.657(2) 165(2) 1_655 N2 H103 O1 0.92(3) 2.01(3) 2.927(3) 177(3) 3_656 N1 H100 O2 1.11(3) 1.56(3) 2.628(2) 161(2) 2_655 C2 H2 Cg1 0.929 2.828 3.7452(31) 169.342(181) . C13 H13 Cg2 0.929 2.829 3.7464(26) 169.660(157) 1_455 N4 H105 Cg1 0.86(4) 3.24(3) 3.97(4) 146.171(251) 3_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.211 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.041 #====END data_5 #TrackingRef '- cif.txt' _database_code_depnum_ccdc_archive 'CCDC 866264' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 N2 O8' _chemical_formula_weight 358.35 _chemical_absolute_configuration unk 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 Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.1192(14) _cell_length_b 15.328(3) _cell_length_c 15.729(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1716.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14101 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16287 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2250 _reflns_number_gt 1860 _reflns_threshold_expression >2sigma(I) _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-XP _computing_publication_material 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. Considering the meaningless absolute structure parameter value, Friedel-pair reflections is merged with the MERG 3 instruction before final refinement. ; _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^)+(0.0946P)^2^+0.0678P] 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 2250 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.8505(2) 0.14113(17) 0.22919(14) 0.0519(6) Uani 1 1 d . . . O2 O 0.8427(2) 0.15074(14) 0.08789(13) 0.0424(5) Uani 1 1 d . . . O3 O 0.4807(3) 0.14636(15) 0.24194(13) 0.0463(5) Uani 1 1 d . . . H3 H 0.3898 0.1136 0.2448 0.069 Uiso 1 1 calc R . . O4 O 0.5447(3) 0.30162(13) 0.1441(2) 0.0598(7) Uani 1 1 d . . . H4 H 0.4558 0.3348 0.1514 0.090 Uiso 1 1 calc R . . O5 O 0.1872(2) 0.15456(12) 0.07986(13) 0.0399(4) Uani 1 1 d . . . O6 O 0.1848(3) 0.28952(14) 0.13186(19) 0.0577(6) Uani 1 1 d . . . O7 O 0.1741(3) 0.0379(2) 0.2585(2) 0.0659(7) Uani 1 1 d . . . O8 O 0.8712(3) 0.40117(17) 0.1309(3) 0.0860(10) Uani 1 1 d . . . N1 N 0.2994(4) 0.65171(15) 0.10067(16) 0.0395(5) Uani 1 1 d . . . N2 N 0.2848(6) 0.9642(2) 0.0932(3) 0.0793(11) Uani 1 1 d . . . C1 C 0.3060(4) 0.57464(19) 0.0635(2) 0.0500(7) Uani 1 1 d . . . C2 C 0.3034(5) 0.5696(2) -0.0245(2) 0.0579(9) Uani 1 1 d . . . H2 H 0.3048 0.5152 -0.0507 0.069 Uiso 1 1 calc R . . C3 C 0.2988(4) 0.6426(3) -0.0727(2) 0.0559(8) Uani 1 1 d . . . C4 C 0.2974(4) 0.7255(2) -0.03333(17) 0.0431(6) Uani 1 1 d . . . C5 C 0.2956(3) 0.72846(17) 0.05702(17) 0.0357(5) Uani 1 1 d . . . C6 C 0.2960(5) 0.8055(3) -0.0768(2) 0.0585(8) Uani 1 1 d . . . H6 H 0.2970 0.8060 -0.1359 0.070 Uiso 1 1 calc R . . C7 C 0.2933(5) 0.8806(2) -0.0347(3) 0.0595(9) Uani 1 1 d . . . H7 H 0.2945 0.9323 -0.0655 0.071 Uiso 1 1 calc R . . C8 C 0.2886(4) 0.88505(18) 0.0550(3) 0.0544(8) Uani 1 1 d . . . C9 C 0.2910(4) 0.80686(19) 0.1015(2) 0.0454(6) Uani 1 1 d . . . H9 H 0.2896 0.8075 0.1606 0.054 Uiso 1 1 calc R . . C10 C 0.3180(6) 0.4955(2) 0.1190(3) 0.0805(13) Uani 1 1 d . . . H10A H 0.3957 0.5080 0.1673 0.121 Uiso 1 1 calc R . . H10B H 0.3715 0.4481 0.0873 0.121 Uiso 1 1 calc R . . H10C H 0.1944 0.4796 0.1378 0.121 Uiso 1 1 calc R . . C11 C 0.2929(8) 0.6358(4) -0.1690(3) 0.0982(18) Uani 1 1 d . . . H11A H 0.2453 0.5796 -0.1851 0.147 Uiso 1 1 calc R . . H11B H 0.4173 0.6431 -0.1915 0.147 Uiso 1 1 calc R . . H11C H 0.2124 0.6805 -0.1914 0.147 Uiso 1 1 calc R . . C12 C 0.7677(3) 0.14643(15) 0.16111(17) 0.0319(5) Uani 1 1 d . . . C13 C 0.5520(3) 0.14603(16) 0.15826(16) 0.0307(5) Uani 1 1 d . . . H13 H 0.5108 0.0922 0.1302 0.037 Uiso 1 1 calc R . . C14 C 0.4799(3) 0.22296(16) 0.10732(18) 0.0350(5) Uani 1 1 d . . . H14 H 0.5263 0.2187 0.0488 0.042 Uiso 1 1 calc R . . C15 C 0.2645(3) 0.22416(16) 0.10657(17) 0.0341(5) Uani 1 1 d . . . H100 H 0.272(9) 1.012(5) 0.055(5) 0.12(2) Uiso 1 1 d . . . H101 H 0.244(4) 0.9593(19) 0.163(2) 0.036(7) Uiso 1 1 d . . . H102 H 0.304(5) 0.650(2) 0.149(2) 0.042(9) Uiso 1 1 d . . . H103 H 0.079(8) 0.072(4) 0.259(3) 0.102(18) Uiso 1 1 d . . . H104 H 0.118(4) -0.0051(19) 0.2960(18) 0.072(12) Uiso 1 1 d . . . H105 H 0.9049 0.3344 0.1250 0.087 Uiso 1 1 d R . . H106 H 0.8519 0.3782 0.1850 0.087 Uiso 1 1 d R . . H107 H 0.973(9) 0.154(3) 0.097(3) 0.098(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0245(8) 0.0820(16) 0.0491(11) 0.0039(11) -0.0082(8) 0.0021(9) O2 0.0204(8) 0.0582(12) 0.0486(11) -0.0098(9) -0.0006(7) -0.0010(8) O3 0.0295(9) 0.0670(13) 0.0423(10) 0.0040(10) 0.0030(8) -0.0067(9) O4 0.0310(9) 0.0292(10) 0.119(2) -0.0022(12) -0.0054(12) -0.0048(7) O5 0.0205(7) 0.0421(10) 0.0570(11) -0.0067(9) -0.0020(7) 0.0022(7) O6 0.0291(9) 0.0401(11) 0.1039(18) -0.0086(11) 0.0048(11) 0.0076(8) O7 0.0404(11) 0.0764(17) 0.0808(17) 0.0225(14) 0.0006(12) -0.0016(12) O8 0.0393(11) 0.0468(13) 0.172(3) -0.0277(16) -0.0025(18) -0.0011(10) N1 0.0447(12) 0.0355(11) 0.0381(12) 0.0019(10) -0.0027(10) -0.0023(10) N2 0.072(2) 0.0368(15) 0.130(3) -0.0174(19) -0.002(2) -0.0026(14) C1 0.0372(14) 0.0400(15) 0.073(2) -0.0093(13) -0.0048(15) -0.0025(12) C2 0.0480(17) 0.0492(17) 0.076(2) -0.0287(16) -0.0111(17) 0.0047(14) C3 0.0415(15) 0.075(2) 0.0513(16) -0.0251(16) -0.0047(14) 0.0074(16) C4 0.0338(13) 0.0545(16) 0.0411(13) 0.0051(12) -0.0032(11) -0.0016(12) C5 0.0298(12) 0.0336(12) 0.0439(13) 0.0014(10) -0.0015(11) 0.0012(10) C6 0.0543(18) 0.066(2) 0.0552(18) 0.0173(16) -0.0016(16) 0.0043(16) C7 0.0470(17) 0.0543(19) 0.077(2) 0.0218(17) -0.0027(17) 0.0018(14) C8 0.0362(14) 0.0297(13) 0.097(3) -0.0066(15) -0.0026(17) -0.0017(11) C9 0.0413(14) 0.0401(14) 0.0546(16) -0.0058(12) -0.0020(14) -0.0030(12) C10 0.081(3) 0.0326(16) 0.128(4) 0.0138(19) -0.005(3) -0.0057(17) C11 0.092(3) 0.148(5) 0.055(2) -0.040(3) -0.017(2) 0.023(3) C12 0.0226(10) 0.0263(11) 0.0467(13) -0.0046(10) -0.0018(9) -0.0013(8) C13 0.0229(10) 0.0291(11) 0.0401(12) -0.0024(10) 0.0008(9) -0.0014(8) C14 0.0204(10) 0.0327(12) 0.0519(14) 0.0040(11) 0.0050(10) -0.0017(9) C15 0.0222(10) 0.0340(12) 0.0459(13) 0.0062(10) 0.0012(9) 0.0021(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 C12 1.225(3) . ? O2 C12 1.271(3) . ? O2 H107 0.94(6) . ? O3 C13 1.411(3) . ? O3 H3 0.8200 . ? O4 C14 1.415(3) . ? O4 H4 0.8200 . ? O5 C15 1.272(3) . ? O6 C15 1.218(3) . ? O7 H103 0.86(6) . ? O7 H104 0.97(3) . ? O8 H105 1.0547 . ? O8 H106 0.9299 . ? N1 C1 1.319(4) . ? N1 C5 1.362(4) . ? N1 H102 0.76(4) . ? N2 C8 1.355(4) . ? N2 H100 0.95(7) . ? N2 H101 1.15(3) . ? C1 C2 1.386(5) . ? C1 C10 1.497(5) . ? C2 C3 1.353(5) . ? C2 H2 0.9300 . ? C3 C4 1.414(5) . ? C3 C11 1.519(5) . ? C4 C6 1.404(5) . ? C4 C5 1.422(4) . ? C5 C9 1.391(4) . ? C6 C7 1.327(5) . ? C6 H6 0.9300 . ? C7 C8 1.413(6) . ? C7 H7 0.9300 . ? C8 C9 1.404(5) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.537(3) . ? C13 C14 1.515(3) . ? C13 H13 0.9800 . ? C14 C15 1.534(3) . ? C14 H14 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O2 H107 106(3) . . ? C13 O3 H3 109.5 . . ? C14 O4 H4 109.5 . . ? H103 O7 H104 95(4) . . ? H105 O8 H106 75.4 . . ? C1 N1 C5 123.4(3) . . ? C1 N1 H102 114(3) . . ? C5 N1 H102 122(3) . . ? C8 N2 H100 114(4) . . ? C8 N2 H101 111.9(15) . . ? H100 N2 H101 130(5) . . ? N1 C1 C2 119.5(3) . . ? N1 C1 C10 118.0(3) . . ? C2 C1 C10 122.5(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 C11 120.2(4) . . ? C4 C3 C11 119.9(4) . . ? C6 C4 C3 124.8(3) . . ? C6 C4 C5 117.3(3) . . ? C3 C4 C5 117.8(3) . . ? N1 C5 C9 119.5(2) . . ? N1 C5 C4 118.4(3) . . ? C9 C5 C4 122.1(3) . . ? C7 C6 C4 120.9(3) . . ? C7 C6 H6 119.5 . . ? C4 C6 H6 119.5 . . ? C6 C7 C8 122.8(3) . . ? C6 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? N2 C8 C9 122.3(4) . . ? N2 C8 C7 119.1(4) . . ? C9 C8 C7 118.6(3) . . ? C5 C9 C8 118.4(3) . . ? C5 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 O2 126.4(2) . . ? O1 C12 C13 120.4(2) . . ? O2 C12 C13 113.2(2) . . ? O3 C13 C14 111.6(2) . . ? O3 C13 C12 109.4(2) . . ? C14 C13 C12 110.5(2) . . ? O3 C13 H13 108.4 . . ? C14 C13 H13 108.4 . . ? C12 C13 H13 108.4 . . ? O4 C14 C13 109.7(2) . . ? O4 C14 C15 108.6(2) . . ? C13 C14 C15 110.6(2) . . ? O4 C14 H14 109.3 . . ? C13 C14 H14 109.3 . . ? C15 C14 H14 109.3 . . ? O6 C15 O5 126.6(2) . . ? O6 C15 C14 118.2(2) . . ? O5 C15 C14 115.2(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 C10 H10B O4 0.96 2.71 3.405(4) 129.5 . C10 H10B O6 0.96 2.86 3.303(4) 109.4 . O2 H107 O5 0.94(6) 1.55(6) 2.457(2) 161(5) 1_655 O2 H107 O6 0.94(6) 2.63(5) 3.307(3) 130(4) 1_655 C7 H7 O8 0.93 2.81 3.714(5) 165.8 4_465 C11 H11C O6 0.96 2.91 3.338(6) 108.2 2_564 O8 H106 O4 0.93 2.56 2.788(3) 94.0 . O7 H104 O8 0.97(3) 1.84(3) 2.743(4) 153(3) 3_645 O7 H103 O1 0.86(6) 2.00(6) 2.832(3) 165(5) 1_455 N1 H102 O3 0.76(4) 2.31(4) 2.930(3) 140(3) 3_655 N1 H102 O1 0.76(4) 2.22(4) 2.886(3) 148(4) 3_655 N2 H101 O7 1.15(3) 1.98(3) 2.943(6) 139(2) 1_565 N2 H100 O5 0.95(7) 2.31(7) 3.006(4) 130(6) 1_565 O4 H4 O6 0.82 2.07 2.576(3) 119.4 . O3 H3 O7 0.82 1.94 2.756(3) 176.7 . C2 H2 O2 0.93 2.62 3.533(4) 165.6 4_455 C10 H10C O8 0.96 2.60 3.499(5) 156.3 1_455 C13 H13 N2 0.98 2.60 3.526(4) 156.9 1_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.253 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.048 #====END